#########################################################################
#									#
#            	THIS IS AN EXAMPLE OF A CIF REPORTING MULTIPLE 		#
#	 	STRUCTURES AND INCLUDING USER-DEFINABLE TEXT		#
#		SECTIONS						#
#									#
#########################################################################

data_global

loop_
_publ_body_element
_publ_body_title
_publ_body_contents

 section . 
;
?
;
 section 
;
Introduction
; 
;\
INTRODUCTION TEXT HERE
;
 section Experimental 
;
?
;
 subsection 'Synthesis and crystallization'
;
TEXT HERE
;

 subsection Refinement
;
TEXT HERE
;

 section 'Results and discussion'
;
TEXT HERE
;

#=============================================================

_audit_creation_date        'June 17, 2013'
_audit_creation_method      'from SHELXL-97'
_audit_update_record
;
;

#===================================================================
# 1. SUBMISSION DETAILS

_publ_contact_author_name       'NAME'
_publ_contact_author_address
;
ADDRESS
;

_publ_contact_author_phone      ?
_publ_contact_author_fax        ?
_publ_contact_author_email      ?

_publ_requested_journal         'Acta Crystallographica C'
_publ_requested_category        FA
_publ_requested_coeditor_name   ?

_publ_contact_letter
;
;

#=====================================================================
# 2. PROCESSING SUMMARY  (IUCr Office Use Only)

_journal_date_recd_electronic     ?
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted            ?
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code            ?
_journal_paper_doi                ?
_journal_paper_category           FA
_journal_coeditor_notes           ?
_journal_techeditor_code          ?
_iucr_compatibility_tag           ACTA95
_journal_techeditor_notes         ?
_journal_coden_ASTM               ACSCGG
_journal_name_full                'Acta Crystallographica, Section C'
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

#=====================================================================
# 3. TITLE AND AUTHOR LIST

_publ_section_title
;
TITLE
;

loop_
_publ_author_name
_publ_author_address
_publ_author_email
_publ_author_footnote
'NAME'
;  
ADDRESS
;
? ?

#======================================================================
# 4. TEXT

_publ_section_synopsis
;
TEXT HERE
;

_publ_section_keywords
;
TEXT HERE
;

_publ_section_abstract
;
TEXT HERE
;

_publ_section_references
;
REFERENCES HERE
;

_publ_section_figure_captions  
;
FIGURE CAPTIONS HERE
;

_publ_section_table_legends
;
TABLE CAPTIONS HERE
;

_publ_section_acknowledgements
;
ACKNOWLEDGEMENTS HERE
;

#=====================================================================

data_I

#=====================================================================
# 5. Chemical Data

_chemical_name_systematic
;\
(6R*,11R*)-5-Acetyl-11-ethyl-6,11-dihydro-5H-\
dibenzo[b,e]azepine-6-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C19 H19 N O3' 
_chemical_formula_sum             'C19 H19 N O3' 
_chemical_formula_weight          309.35 
_chemical_compound_source         'synthesised by authors, see text'
_chemical_formula_iupac           'C19 H19 N O3' 

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21'
_symmetry_space_group_name_Hall   'P 2yb'

loop_
 _symmetry_equiv_pos_as_xyz
'x, y, z' 
 '-x, y+1/2, -z' 

_cell_length_a                    8.8053(3) 
_cell_length_b                    10.9821(4) 
_cell_length_c                    9.0080(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  118.510(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      765.45(6) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     1853
_cell_measurement_theta_min       3.20
_cell_measurement_theta_max       27.50

_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.14
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              328
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min   0.977
_exptl_absorpt_correction_T_max   0.991

_exptl_special_details
?

_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_source          'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method        'φ and ω'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_number          0
_diffrn_standards_decay_%         0

_diffrn_reflns_number             13276 
_diffrn_reflns_av_R_equivalents   0.0486 
_diffrn_reflns_av_sigmaI/netI     0.0321 
_diffrn_reflns_limit_h_min       -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min       -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min       -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          3.71
_diffrn_reflns_theta_max          27.50
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_max    0.997
_diffrn_measured_fraction_theta_full   0.997
_reflns_number_total              1851
_reflns_number_gt                 1638
_reflns_threshold_expression      I>2σ(I)

_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        
'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction         
'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'  
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material 
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;

#=========================================================================
# 8. Refinement Data

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0351P)²+0.1657P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          1851 
_refine_ls_number_parameters      210 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0455 
_refine_ls_R_factor_gt            0.0360 
_refine_ls_wR_factor_ref          0.0807 
_refine_ls_wR_factor_gt           0.0772 
_refine_ls_goodness_of_fit_ref    1.146 
_refine_ls_restrained_S_all       1.146 
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max          0.209
_refine_diff_density_min         -0.240

#=========================================================================
# 9. Atomic Coordinates and Displacement Parameters

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6424(3) 0.5942(2) 0.7939(3) 0.0186(5) Uani 1 1 d . . . 
H1 H 0.6599 0.6154 0.9031 0.022 Uiso 1 1 calc R . . 
C2 C 0.7828(3) 0.5595(2) 0.7731(3) 0.0211(5) Uani 1 1 d . . . 
H2 H 0.8953 0.5589 0.8678 0.025 Uiso 1 1 calc R . . 
C3 C 0.7604(3) 0.5255(2) 0.6149(3) 0.0202(5) Uani 1 1 d . . . 
H3 H 0.8563 0.4993 0.6019 0.024 Uiso 1 1 calc R . . 
C4 C 0.5955(3) 0.5306(2) 0.4757(3) 0.0166(5) Uani 1 1 d . . . 
H4 H 0.5780 0.5079 0.3669 0.020 Uiso 1 1 calc R . . 
C4a C 0.4576(3) 0.5687(2) 0.4973(3) 0.0142(5) Uani 1 1 d . . . 
N5 N 0.2883(2) 0.58197(17) 0.3533(2) 0.0132(4) Uani 1 1 d . . . 
C6 C 0.1469(3) 0.4966(2) 0.3244(3) 0.0128(4) Uani 1 1 d . . . 
H6 H 0.0389 0.5461 0.2831 0.015 Uiso 1 1 calc R . . 
C6a C 0.1714(3) 0.4295(2) 0.4842(3) 0.0145(5) Uani 1 1 d . . . 
C7 C 0.1243(3) 0.3077(2) 0.4737(3) 0.0174(5) Uani 1 1 d . . . 
H7 H 0.0884 0.2652 0.3704 0.021 Uiso 1 1 calc R . . 
C8 C 0.1286(3) 0.2465(2) 0.6107(3) 0.0189(5) Uani 1 1 d . . . 
H8 H 0.0977 0.1628 0.6008 0.023 Uiso 1 1 calc R . . 
C9 C 0.1780(3) 0.3073(2) 0.7616(3) 0.0188(5) Uani 1 1 d . . . 
H9 H 0.1759 0.2670 0.8540 0.023 Uiso 1 1 calc R . . 
C10 C 0.2305(3) 0.4277(2) 0.7762(3) 0.0185(5) Uani 1 1 d . . . 
H10 H 0.2674 0.4685 0.8808 0.022 Uiso 1 1 calc R . . 
C10a C 0.2307(3) 0.4909(2) 0.6412(3) 0.0151(5) Uani 1 1 d . . . 
C11 C 0.3097(3) 0.6185(2) 0.6677(3) 0.0150(5) Uani 1 1 d . . . 
H11 H 0.2307 0.6694 0.5686 0.018 Uiso 1 1 calc R . . 
C11a C 0.4763(3) 0.5982(2) 0.6566(3) 0.0145(5) Uani 1 1 d . . . 
C51 C 0.2534(3) 0.6720(2) 0.2388(3) 0.0142(5) Uani 1 1 d . . . 
O51 O 0.10670(19) 0.68043(16) 0.11339(19) 0.0180(4) Uani 1 1 d . . . 
C52 C 0.3950(3) 0.7609(2) 0.2675(3) 0.0189(5) Uani 1 1 d . . . 
H52A H 0.4784 0.7219 0.2397 0.028 Uiso 1 1 calc R . . 
H52B H 0.4537 0.7862 0.3862 0.028 Uiso 1 1 calc R . . 
H52C H 0.3452 0.8324 0.1952 0.028 Uiso 1 1 calc R . . 
C61 C 0.1208(3) 0.4093(2) 0.1806(3) 0.0145(5) Uani 1 1 d . . . 
O61 O -0.0387(2) 0.36474(17) 0.10291(19) 0.0186(4) Uani 1 1 d . . . 
H61 H -0.0487 0.3107 0.0297 0.028 Uiso 1 1 d R . . 
O62 O 0.2327(2) 0.38608(17) 0.1438(2) 0.0224(4) Uani 1 1 d . . . 
C111 C 0.3325(3) 0.6837(2) 0.8280(3) 0.0202(5) Uani 1 1 d . . . 
H11A H 0.2247 0.6761 0.8362 0.024 Uiso 1 1 calc R . . 
H11B H 0.4266 0.6440 0.9284 0.024 Uiso 1 1 calc R . . 
C112 C 0.3752(3) 0.8181(2) 0.8272(3) 0.0229(5) Uani 1 1 d . . . 
H12A H 0.4821 0.8260 0.8195 0.034 Uiso 1 1 calc R . . 
H12B H 0.3905 0.8565 0.9317 0.034 Uiso 1 1 calc R . . 
H12C H 0.2804 0.8583 0.7300 0.034 Uiso 1 1 calc R . . 


#=========================================================================
# 10. Molecular Geometry

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.388(4) . ? 
C1 C11a 1.395(3) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.393(4) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.395(3) . ? 
C3 H3 0.9500 . ? 
C4 C4a 1.383(3) . ? 
C4 H4 0.9500 . ? 
C4a C11a 1.402(3) . ? 
C4a N5 1.442(3) . ? 
N5 C51 1.354(3) . ? 
N5 C6 1.479(3) . ? 
C6 C6a 1.538(3) . ? 
C6 C61 1.538(3) . ? 
C6 H6 1.0000 . ? 
C6a C7 1.390(3) . ? 
C6a C10a 1.423(3) . ? 
C7 C8 1.390(3) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.386(3) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.386(3) . ? 
C9 H9 0.9500 . ? 
C10 C10a 1.401(3) . ? 
C10 H10 0.9500 . ? 
C10a C11 1.532(3) . ? 
C11 C11a 1.533(3) . ? 
C11 C111 1.536(3) . ? 
C11 H11 1.0000 . ? 
C51 O51 1.249(3) . ? 
C51 C52 1.506(3) . ? 
C52 H52A 0.9800 . ? 
C52 H52B 0.9800 . ? 
C52 H52C 0.9800 . ? 
C61 O62 1.207(3) . ? 
C61 O61 1.328(3) . ? 
O61 H61 0.8602 . ? 
C111 C112 1.523(4) . ? 
C111 H11A 0.9900 . ? 
C111 H11B 0.9900 . ? 
C112 H12A 0.9800 . ? 
C112 H12B 0.9800 . ? 
C112 H12C 0.9800 . ? 

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C11a 120.9(2) . . ? 
C2 C1 H1 119.5 . . ? 
C11a C1 H1 119.5 . . ? 
C1 C2 C3 120.7(2) . . ? 
C1 C2 H2 119.6 . . ? 
C3 C2 H2 119.6 . . ? 
C2 C3 C4 119.1(2) . . ? 
C2 C3 H3 120.4 . . ? 
C4 C3 H3 120.4 . . ? 
C4a C4 C3 119.6(2) . . ? 
C4a C4 H4 120.2 . . ? 
C3 C4 H4 120.2 . . ? 
C4 C4a C11a 122.1(2) . . ? 
C4 C4a N5 120.27(19) . . ? 
C11a C4a N5 117.61(19) . . ? 
C51 N5 C4a 121.36(18) . . ? 
C51 N5 C6 117.57(18) . . ? 
C4a N5 C6 121.06(17) . . ? 
N5 C6 C6a 114.16(18) . . ? 
N5 C6 C61 108.54(17) . . ? 
C6a C6 C61 112.80(19) . . ? 
N5 C6 H6 107.0 . . ? 
C6a C6 H6 107.0 . . ? 
C61 C6 H6 107.0 . . ? 
C7 C6a C10a 118.7(2) . . ? 
C7 C6a C6 119.6(2) . . ? 
C10a C6a C6 121.6(2) . . ? 
C8 C7 C6a 121.6(2) . . ? 
C8 C7 H7 119.2 . . ? 
C6a C7 H7 119.2 . . ? 
C9 C8 C7 120.0(2) . . ? 
C9 C8 H8 120.0 . . ? 
C7 C8 H8 120.0 . . ? 
C8 C9 C10 119.2(2) . . ? 
C8 C9 H9 120.4 . . ? 
C10 C9 H9 120.4 . . ? 
C9 C10 C10a 122.0(2) . . ? 
C9 C10 H10 119.0 . . ? 
C10a C10 H10 119.0 . . ? 
C10 C10a C6a 118.4(2) . . ? 
C10 C10a C11 120.5(2) . . ? 
C6a C10a C11 120.8(2) . . ? 
C10a C11 C11a 103.51(18) . . ? 
C10a C11 C111 114.78(19) . . ? 
C11a C11 C111 115.41(19) . . ? 
C10a C11 H11 107.6 . . ? 
C11a C11 H11 107.6 . . ? 
C111 C11 H11 107.6 . . ? 
C1 C11a C4a 117.4(2) . . ? 
C1 C11a C11 125.3(2) . . ? 
C4a C11a C11 116.87(19) . . ? 
O51 C51 N5 120.3(2) . . ? 
O51 C51 C52 121.4(2) . . ? 
N5 C51 C52 118.30(19) . . ? 
C51 C52 H52A 109.5 . . ? 
C51 C52 H52B 109.5 . . ? 
H52A C52 H52B 109.5 . . ? 
C51 C52 H52C 109.5 . . ? 
H52A C52 H52C 109.5 . . ? 
H52B C52 H52C 109.5 . . ? 
O62 C61 O61 125.0(2) . . ? 
O62 C61 C6 123.3(2) . . ? 
O61 C61 C6 111.64(18) . . ? 
C61 O61 H61 110.7 . . ? 
C112 C111 C11 111.7(2) . . ? 
C112 C111 H11A 109.3 . . ? 
C11 C111 H11A 109.3 . . ? 
C112 C111 H11B 109.3 . . ? 
C11 C111 H11B 109.3 . . ? 
H11A C111 H11B 108.0 . . ? 
C111 C112 H12A 109.5 . . ? 
C111 C112 H12B 109.5 . . ? 
H12A C112 H12B 109.5 . . ? 
C111 C112 H12C 109.5 . . ? 
H12A C112 H12C 109.5 . . ? 
H12B C112 H12C 109.5 . . ? 

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C11a C1 C2 C3 -1.3(4) . . . . ? 
C1 C2 C3 C4 2.1(4) . . . . ? 
C2 C3 C4 C4a -0.1(4) . . . . ? 
C3 C4 C4a C11a -2.7(4) . . . . ? 
C3 C4 C4a N5 176.0(2) . . . . ? 
C4 C4a N5 C51 -70.0(3) . . . . ? 
C11a C4a N5 C51 108.7(2) . . . . ? 
C4 C4a N5 C6 109.3(2) . . . . ? 
C11a C4a N5 C6 -72.0(3) . . . . ? 
C51 N5 C6 C6a -158.55(19) . . . . ? 
C4a N5 C6 C6a 22.1(3) . . . . ? 
C51 N5 C6 C61 74.7(2) . . . . ? 
C4a N5 C6 C61 -104.7(2) . . . . ? 
N5 C6 C6a C7 -141.2(2) . . . . ? 
C61 C6 C6a C7 -16.7(3) . . . . ? 
N5 C6 C6a C10a 42.9(3) . . . . ? 
C61 C6 C6a C10a 167.43(19) . . . . ? 
C10a C6a C7 C8 2.2(3) . . . . ? 
C6 C6a C7 C8 -173.8(2) . . . . ? 
C6a C7 C8 C9 1.0(4) . . . . ? 
C7 C8 C9 C10 -3.0(3) . . . . ? 
C8 C9 C10 C10a 1.8(3) . . . . ? 
C9 C10 C10a C6a 1.4(3) . . . . ? 
C9 C10 C10a C11 -172.7(2) . . . . ? 
C7 C6a C10a C10 -3.4(3) . . . . ? 
C6 C6a C10a C10 172.6(2) . . . . ? 
C7 C6a C10a C11 170.7(2) . . . . ? 
C6 C6a C10a C11 -13.4(3) . . . . ? 
C10 C10a C11 C11a 108.4(2) . . . . ? 
C6a C10a C11 C11a -65.6(3) . . . . ? 
C10 C10a C11 C111 -18.3(3) . . . . ? 
C6a C10a C11 C111 167.7(2) . . . . ? 
C2 C1 C11a C4a -1.4(3) . . . . ? 
C2 C1 C11a C11 171.5(2) . . . . ? 
C4 C4a C11a C1 3.4(3) . . . . ? 
N5 C4a C11a C1 -175.3(2) . . . . ? 
C4 C4a C11a C11 -170.1(2) . . . . ? 
N5 C4a C11a C11 11.2(3) . . . . ? 
C10a C11 C11a C1 -103.1(3) . . . . ? 
C111 C11 C11a C1 23.1(4) . . . . ? 
C10a C11 C11a C4a 69.8(2) . . . . ? 
C111 C11 C11a C4a -163.9(2) . . . . ? 
C4a N5 C51 O51 178.7(2) . . . . ? 
C6 N5 C51 O51 -0.7(3) . . . . ? 
C4a N5 C51 C52 -1.5(3) . . . . ? 
C6 N5 C51 C52 179.1(2) . . . . ? 
N5 C6 C61 O62 24.4(3) . . . . ? 
C6a C6 C61 O62 -103.1(3) . . . . ? 
N5 C6 C61 O61 -155.01(18) . . . . ? 
C6a C6 C61 O61 77.5(2) . . . . ? 
C10a C11 C111 C112 -168.0(2) . . . . ? 
C11a C11 C111 C112 71.7(3) . . . . ? 

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
 _geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D   H    A   D-H   H...A  D...A    D-H...A  symm  publ
# -   -    -   ---   -----  -----    -------  ----  ----
 O61  H61  O51 0.86  1.83   2.672(2) 167      2_545 no
 C2   H2   O51 0.95  2.49   3.309(3) 144      1_656 no
 C112 H12A O62 0.98  2.46   3.418(4) 165      2_656 no

#======================================================================


#======================================================================

data_II

#=====================================================================
# 5. Chemical Data

_chemical_name_systematic
;
(6RS,11SR)-5-Acetyl-11-ethyl-2-methyl-6,11-dihydro-\
5H-dibenzo[b,e]azepine-6-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C20 H21 N O3' 
_chemical_formula_sum             'C20 H21 N O3' 
_chemical_formula_weight          323.38 
_chemical_compound_source         'synthesised by authors, see text'
_chemical_formula_iupac           'C20 H21 N O3' 

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21/c'
_symmetry_space_group_name_Hall   '-P 2ybc'

loop_
 _symmetry_equiv_pos_as_xyz
'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 

_cell_length_a                    15.2894(16) 
_cell_length_b                    10.760(2) 
_cell_length_c                    10.538(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  100.990(11) 
_cell_angle_gamma                 90.00 
_cell_volume                      1701.9(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3906
_cell_measurement_theta_min       2.65
_cell_measurement_theta_max       27.50

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.41
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.24
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.262
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              688
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min   0.966
_exptl_absorpt_correction_T_max   0.980

_exptl_special_details
?

_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_source          'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method        'φ and ω'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_number          0
_diffrn_standards_decay_%         0

_diffrn_reflns_number             28096 
_diffrn_reflns_av_R_equivalents   0.0915 
_diffrn_reflns_av_sigmaI/netI     0.0603 
_diffrn_reflns_limit_h_min       -19 
_diffrn_reflns_limit_h_max        19 
_diffrn_reflns_limit_k_min       -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min       -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.50
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_max    0.998
_diffrn_measured_fraction_theta_full   0.998
_reflns_number_total              3903
_reflns_number_gt                 2589
_reflns_threshold_expression      I>2σ(I)


_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        
'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction         
'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'  
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material 
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;


#=========================================================================
# 8. Refinement Data

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0624P)²+1.5377P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3903 
_refine_ls_number_parameters      220 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1051 
_refine_ls_R_factor_gt            0.0586 
_refine_ls_wR_factor_ref          0.1548 
_refine_ls_wR_factor_gt           0.1302 
_refine_ls_goodness_of_fit_ref    1.050 
_refine_ls_restrained_S_all       1.050 
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max          0.678
_refine_diff_density_min         -0.292

#=========================================================================
# 9. Atomic Coordinates and Displacement Parameters

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.11423(15) 0.5736(2) 0.1081(2) 0.0183(5) Uani 1 1 d . . . 
H1 H 0.0551 0.5673 0.1234 0.022 Uiso 1 1 calc R . . 
C2 C 0.13034(15) 0.6464(2) 0.0050(2) 0.0200(5) Uani 1 1 d . . . 
C3 C 0.21783(16) 0.6576(2) -0.0142(2) 0.0203(5) Uani 1 1 d . . . 
H3 H 0.2303 0.7089 -0.0819 0.024 Uiso 1 1 calc R . . 
C4 C 0.28655(15) 0.5946(2) 0.0642(2) 0.0189(5) Uani 1 1 d . . . 
H4 H 0.3459 0.6025 0.0502 0.023 Uiso 1 1 calc R . . 
C4a C 0.26855(14) 0.5197(2) 0.1637(2) 0.0160(5) Uani 1 1 d . . . 
N5 N 0.33846(12) 0.45422(17) 0.24821(17) 0.0153(4) Uani 1 1 d . . . 
C6 C 0.36955(15) 0.5095(2) 0.3762(2) 0.0164(5) Uani 1 1 d . . . 
H6 H 0.4184 0.4543 0.4213 0.020 Uiso 1 1 calc R . . 
C6a C 0.30137(15) 0.5169(2) 0.4643(2) 0.0166(5) Uani 1 1 d . . . 
C7 C 0.33741(16) 0.5563(2) 0.5908(2) 0.0216(5) Uani 1 1 d . . . 
H7 H 0.3989 0.5765 0.6123 0.026 Uiso 1 1 calc R . . 
C8 C 0.28551(17) 0.5662(2) 0.6846(2) 0.0257(5) Uani 1 1 d . . . 
H8 H 0.3111 0.5930 0.7694 0.031 Uiso 1 1 calc R . . 
C9 C 0.19597(18) 0.5366(2) 0.6534(2) 0.0267(6) Uani 1 1 d . . . 
H9 H 0.1594 0.5439 0.7165 0.032 Uiso 1 1 calc R . . 
C10 C 0.15979(16) 0.4962(2) 0.5295(2) 0.0220(5) Uani 1 1 d . . . 
H10 H 0.0983 0.4754 0.5094 0.026 Uiso 1 1 calc R . . 
C10a C 0.21130(15) 0.4849(2) 0.4325(2) 0.0176(5) Uani 1 1 d . . . 
C11 C 0.16359(14) 0.4346(2) 0.3022(2) 0.0180(5) Uani 1 1 d . . . 
H11 H 0.0985 0.4447 0.3014 0.022 Uiso 1 1 calc R . . 
C11a C 0.18239(15) 0.5102(2) 0.1891(2) 0.0166(5) Uani 1 1 d . . . 
C21 C 0.05529(16) 0.7126(2) -0.0825(2) 0.0279(6) Uani 1 1 d . . . 
H21A H 0.0756 0.7409 -0.1604 0.042 Uiso 1 1 calc R . . 
H21B H 0.0366 0.7844 -0.0371 0.042 Uiso 1 1 calc R . . 
H21C H 0.0049 0.6556 -0.1069 0.042 Uiso 1 1 calc R . . 
C51 C 0.38517(14) 0.3587(2) 0.2100(2) 0.0182(5) Uani 1 1 d . . . 
O51 O 0.44856(11) 0.31255(16) 0.28673(15) 0.0231(4) Uani 1 1 d . . . 
C52 C 0.35754(17) 0.3077(2) 0.0754(2) 0.0265(6) Uani 1 1 d . . . 
H52A H 0.4064 0.3181 0.0282 0.040 Uiso 1 1 calc R . . 
H52B H 0.3049 0.3526 0.0305 0.040 Uiso 1 1 calc R . . 
H52C H 0.3433 0.2192 0.0800 0.040 Uiso 1 1 calc R . . 
C61 C 0.41375(15) 0.6350(2) 0.3559(2) 0.0188(5) Uani 1 1 d . . . 
O61 O 0.47155(11) 0.61912(15) 0.27831(17) 0.0259(4) Uani 1 1 d . . . 
H61 H 0.4981 0.6936 0.2657 0.039 Uiso 1 1 d R . . 
O62 O 0.39924(12) 0.73197(15) 0.40492(16) 0.0270(4) Uani 1 1 d . . . 
C111 C 0.17878(16) 0.2930(2) 0.2890(2) 0.0204(5) Uani 1 1 d . . . 
H11A H 0.1583 0.2681 0.1977 0.024 Uiso 1 1 calc R . . 
H11B H 0.2434 0.2751 0.3125 0.024 Uiso 1 1 calc R . . 
C112 C 0.12941(17) 0.2163(2) 0.3747(2) 0.0254(5) Uani 1 1 d . . . 
H12A H 0.1478 0.2429 0.4648 0.038 Uiso 1 1 calc R . . 
H12B H 0.1437 0.1281 0.3673 0.038 Uiso 1 1 calc R . . 
H12C H 0.0651 0.2286 0.3472 0.038 Uiso 1 1 calc R . . 


#=========================================================================
# 10. Molecular Geometry

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C11a 1.393(3) . ? 
C1 C2 1.398(3) . ? 
C1 H1 0.9500 . ? 
C2 C3 1.396(3) . ? 
C2 C21 1.507(3) . ? 
C3 C4 1.384(3) . ? 
C3 H3 0.9500 . ? 
C4 C4a 1.390(3) . ? 
C4 H4 0.9500 . ? 
C4a C11a 1.397(3) . ? 
C4a N5 1.439(3) . ? 
N5 C51 1.356(3) . ? 
N5 C6 1.468(3) . ? 
C6 C6a 1.524(3) . ? 
C6 C61 1.543(3) . ? 
C6 H6 1.0000 . ? 
C6a C10a 1.397(3) . ? 
C6a C7 1.407(3) . ? 
C7 C8 1.385(3) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.383(4) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.387(3) . ? 
C9 H9 0.9500 . ? 
C10 C10a 1.409(3) . ? 
C10 H10 0.9500 . ? 
C10a C11 1.527(3) . ? 
C11 C11a 1.515(3) . ? 
C11 C111 1.551(3) . ? 
C11 H11 1.0000 . ? 
C21 H21A 0.9800 . ? 
C21 H21B 0.9800 . ? 
C21 H21C 0.9800 . ? 
C51 O51 1.241(3) . ? 
C51 C52 1.504(3) . ? 
C52 H52A 0.9800 . ? 
C52 H52B 0.9800 . ? 
C52 H52C 0.9800 . ? 
C61 O62 1.204(3) . ? 
C61 O61 1.325(3) . ? 
O61 H61 0.9200 . ? 
C111 C112 1.526(3) . ? 
C111 H11A 0.9900 . ? 
C111 H11B 0.9900 . ? 
C112 H12A 0.9800 . ? 
C112 H12B 0.9800 . ? 
C112 H12C 0.9800 . ? 

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C11a C1 C2 121.9(2) . . ? 
C11a C1 H1 119.1 . . ? 
C2 C1 H1 119.1 . . ? 
C3 C2 C1 118.5(2) . . ? 
C3 C2 C21 120.6(2) . . ? 
C1 C2 C21 120.9(2) . . ? 
C4 C3 C2 120.7(2) . . ? 
C4 C3 H3 119.7 . . ? 
C2 C3 H3 119.7 . . ? 
C3 C4 C4a 119.8(2) . . ? 
C3 C4 H4 120.1 . . ? 
C4a C4 H4 120.1 . . ? 
C4 C4a C11a 121.1(2) . . ? 
C4 C4a N5 121.3(2) . . ? 
C11a C4a N5 117.50(19) . . ? 
C51 N5 C4a 123.97(18) . . ? 
C51 N5 C6 118.90(18) . . ? 
C4a N5 C6 116.29(17) . . ? 
N5 C6 C6a 116.21(18) . . ? 
N5 C6 C61 107.51(17) . . ? 
C6a C6 C61 113.99(18) . . ? 
N5 C6 H6 106.1 . . ? 
C6a C6 H6 106.1 . . ? 
C61 C6 H6 106.1 . . ? 
C10a C6a C7 119.4(2) . . ? 
C10a C6a C6 126.77(19) . . ? 
C7 C6a C6 113.8(2) . . ? 
C8 C7 C6a 121.7(2) . . ? 
C8 C7 H7 119.2 . . ? 
C6a C7 H7 119.2 . . ? 
C9 C8 C7 119.2(2) . . ? 
C9 C8 H8 120.4 . . ? 
C7 C8 H8 120.4 . . ? 
C8 C9 C10 119.7(2) . . ? 
C8 C9 H9 120.2 . . ? 
C10 C9 H9 120.2 . . ? 
C9 C10 C10a 122.1(2) . . ? 
C9 C10 H10 118.9 . . ? 
C10a C10 H10 118.9 . . ? 
C6a C10a C10 117.8(2) . . ? 
C6a C10a C11 125.67(19) . . ? 
C10 C10a C11 116.5(2) . . ? 
C11a C11 C10a 112.81(19) . . ? 
C11a C11 C111 113.73(18) . . ? 
C10a C11 C111 112.05(18) . . ? 
C11a C11 H11 105.8 . . ? 
C10a C11 H11 105.8 . . ? 
C111 C11 H11 105.8 . . ? 
C1 C11a C4a 118.0(2) . . ? 
C1 C11a C11 120.9(2) . . ? 
C4a C11a C11 121.1(2) . . ? 
C2 C21 H21A 109.5 . . ? 
C2 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
C2 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
O51 C51 N5 120.0(2) . . ? 
O51 C51 C52 120.8(2) . . ? 
N5 C51 C52 119.2(2) . . ? 
C51 C52 H52A 109.5 . . ? 
C51 C52 H52B 109.5 . . ? 
H52A C52 H52B 109.5 . . ? 
C51 C52 H52C 109.5 . . ? 
H52A C52 H52C 109.5 . . ? 
H52B C52 H52C 109.5 . . ? 
O62 C61 O61 125.2(2) . . ? 
O62 C61 C6 125.3(2) . . ? 
O61 C61 C6 109.52(18) . . ? 
C61 O61 H61 110.0 . . ? 
C112 C111 C11 112.24(19) . . ? 
C112 C111 H11A 109.2 . . ? 
C11 C111 H11A 109.2 . . ? 
C112 C111 H11B 109.2 . . ? 
C11 C111 H11B 109.2 . . ? 
H11A C111 H11B 107.9 . . ? 
C111 C112 H12A 109.5 . . ? 
C111 C112 H12B 109.5 . . ? 
H12A C112 H12B 109.5 . . ? 
C111 C112 H12C 109.5 . . ? 
H12A C112 H12C 109.5 . . ? 
H12B C112 H12C 109.5 . . ? 

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C11a C1 C2 C3 -1.7(3) . . . . ? 
C11a C1 C2 C21 179.1(2) . . . . ? 
C1 C2 C3 C4 2.2(3) . . . . ? 
C21 C2 C3 C4 -178.5(2) . . . . ? 
C2 C3 C4 C4a -0.3(3) . . . . ? 
C3 C4 C4a C11a -2.3(3) . . . . ? 
C3 C4 C4a N5 -179.1(2) . . . . ? 
C4 C4a N5 C51 -67.9(3) . . . . ? 
C11a C4a N5 C51 115.2(2) . . . . ? 
C4 C4a N5 C6 101.4(2) . . . . ? 
C11a C4a N5 C6 -75.5(2) . . . . ? 
C51 N5 C6 C6a -126.5(2) . . . . ? 
C4a N5 C6 C6a 63.6(2) . . . . ? 
C51 N5 C6 C61 104.4(2) . . . . ? 
C4a N5 C6 C61 -65.5(2) . . . . ? 
N5 C6 C6a C10a -4.9(3) . . . . ? 
C61 C6 C6a C10a 121.0(2) . . . . ? 
N5 C6 C6a C7 172.59(19) . . . . ? 
C61 C6 C6a C7 -61.5(3) . . . . ? 
C10a C6a C7 C8 -1.1(3) . . . . ? 
C6 C6a C7 C8 -178.8(2) . . . . ? 
C6a C7 C8 C9 0.0(4) . . . . ? 
C7 C8 C9 C10 0.8(4) . . . . ? 
C8 C9 C10 C10a -0.6(4) . . . . ? 
C7 C6a C10a C10 1.3(3) . . . . ? 
C6 C6a C10a C10 178.6(2) . . . . ? 
C7 C6a C10a C11 -176.7(2) . . . . ? 
C6 C6a C10a C11 0.6(4) . . . . ? 
C9 C10 C10a C6a -0.5(3) . . . . ? 
C9 C10 C10a C11 177.7(2) . . . . ? 
C6a C10a C11 C11a -48.5(3) . . . . ? 
C10 C10a C11 C11a 133.4(2) . . . . ? 
C6a C10a C11 C111 81.4(3) . . . . ? 
C10 C10a C11 C111 -96.7(2) . . . . ? 
C2 C1 C11a C4a -0.8(3) . . . . ? 
C2 C1 C11a C11 178.4(2) . . . . ? 
C4 C4a C11a C1 2.8(3) . . . . ? 
N5 C4a C11a C1 179.75(19) . . . . ? 
C4 C4a C11a C11 -176.4(2) . . . . ? 
N5 C4a C11a C11 0.5(3) . . . . ? 
C10a C11 C11a C1 -116.4(2) . . . . ? 
C111 C11 C11a C1 114.6(2) . . . . ? 
C10a C11 C11a C4a 62.8(3) . . . . ? 
C111 C11 C11a C4a -66.2(3) . . . . ? 
C4a N5 C51 O51 175.1(2) . . . . ? 
C6 N5 C51 O51 6.0(3) . . . . ? 
C4a N5 C51 C52 -6.6(3) . . . . ? 
C6 N5 C51 C52 -175.6(2) . . . . ? 
N5 C6 C61 O62 131.7(2) . . . . ? 
C6a C6 C61 O62 1.4(3) . . . . ? 
N5 C6 C61 O61 -49.6(2) . . . . ? 
C6a C6 C61 O61 -179.92(18) . . . . ? 
C11a C11 C111 C112 -159.48(19) . . . . ? 
C10a C11 C111 C112 71.1(2) . . . . ? 

loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
 _geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D  H   A    D-H   H...A  D...A    D-H...A  symm  publ
# -  -   -    ---   -----  -----    -------  ----  ----
 O61 H61 O51  0.92  1.67   2.572(2) 167      2_655 no
 C4  H4  O62  0.95  2.58   3.220(3) 125      4_575 no
 C8  H8  O62  0.95  2.58   3.405(3) 145      4_576 no


#======================================================================


#======================================================================

data_III

#=====================================================================
# 5. Chemical Data

_chemical_name_systematic
;
(6RS,11SR)-5-Acetyl-11-ethyl-1,3-dimethyl-6,11-dihydro-\
5H-dibenzo[b,e]azepine-6-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C21 H23 N O3' 
_chemical_formula_sum             'C21 H23 N O3' 
_chemical_formula_weight          337.40 
_chemical_compound_source         'synthesised by authors, see text'
_chemical_formula_iupac           'C21 H23 N O3' 

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    'P 21/n'
_symmetry_space_group_name_Hall   '-P 2yn'

loop_
 _symmetry_equiv_pos_as_xyz
'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 

_cell_length_a                    9.2283(11) 
_cell_length_b                    16.691(2) 
_cell_length_c                    11.9824(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  103.820(11) 
_cell_angle_gamma                 90.00 
_cell_volume                      1792.2(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3320
_cell_measurement_theta_min       2.80
_cell_measurement_theta_max       25.50

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.23
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.250
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              720
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min   0.981
_exptl_absorpt_correction_T_max   0.984

_exptl_special_details
?

_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_source          'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method        'φ and ω'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_number          0
_diffrn_standards_decay_%         0

_diffrn_reflns_number             27558 
_diffrn_reflns_av_R_equivalents   0.1392 
_diffrn_reflns_av_sigmaI/netI     0.0758 
_diffrn_reflns_limit_h_min       -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min       -20 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min       -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.89 
_diffrn_reflns_theta_max          25.50 
_diffrn_reflns_theta_full              25.50
_diffrn_measured_fraction_theta_max    0.996
_diffrn_measured_fraction_theta_full   0.996
_reflns_number_total              3316
_reflns_number_gt                 2090
_reflns_threshold_expression      I>2σ(I)


_computing_data_collection        'COLLECT (Nonius, 1998)' 
_computing_cell_refinement        
'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_reduction         
'EVALCCD (Duisenberg et al., 2003)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'  
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'  
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material 
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;


#=========================================================================
# 8. Refinement Data

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0317P)²+1.5359P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3316 
_refine_ls_number_parameters      230 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1188 
_refine_ls_R_factor_gt            0.0575 
_refine_ls_wR_factor_ref          0.1195 
_refine_ls_wR_factor_gt           0.0998 
_refine_ls_goodness_of_fit_ref    1.083 
_refine_ls_restrained_S_all       1.083 
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max          0.245
_refine_diff_density_min         -0.290

#=========================================================================
# 9. Atomic Coordinates and Displacement Parameters

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.3227(3) 0.48561(16) 0.3898(2) 0.0174(6) Uani 1 1 d . . . 
C2 C 0.2439(3) 0.53647(17) 0.4458(2) 0.0197(6) Uani 1 1 d . . . 
H2 H 0.2072 0.5158 0.5076 0.024 Uiso 1 1 calc R . . 
C3 C 0.2165(3) 0.61670(17) 0.4150(2) 0.0205(6) Uani 1 1 d . . . 
C4 C 0.2709(3) 0.64561(17) 0.3246(2) 0.0174(6) Uani 1 1 d . . . 
H4 H 0.2549 0.7001 0.3020 0.021 Uiso 1 1 calc R . . 
C4a C 0.3486(3) 0.59547(15) 0.2670(2) 0.0141(6) Uani 1 1 d . . . 
N5 N 0.4052(2) 0.62796(12) 0.17360(17) 0.0132(5) Uani 1 1 d . . . 
C6 C 0.5661(3) 0.64307(15) 0.1962(2) 0.0146(6) Uani 1 1 d . . . 
H6 H 0.5817 0.6680 0.1241 0.018 Uiso 1 1 calc R . . 
C6a C 0.6650(3) 0.56840(16) 0.2147(2) 0.0155(6) Uani 1 1 d . . . 
C7 C 0.8137(3) 0.58138(16) 0.2103(2) 0.0172(6) Uani 1 1 d . . . 
H7 H 0.8446 0.6342 0.1972 0.021 Uiso 1 1 calc R . . 
C8 C 0.9167(3) 0.51994(17) 0.2243(2) 0.0206(6) Uani 1 1 d . . . 
H8 H 1.0173 0.5308 0.2228 0.025 Uiso 1 1 calc R . . 
C9 C 0.8724(3) 0.44232(17) 0.2404(2) 0.0225(7) Uani 1 1 d . . . 
H9 H 0.9418 0.3993 0.2503 0.027 Uiso 1 1 calc R . . 
C10 C 0.7248(3) 0.42871(16) 0.2419(2) 0.0194(6) Uani 1 1 d . . . 
H10 H 0.6940 0.3753 0.2510 0.023 Uiso 1 1 calc R . . 
C10a C 0.6187(3) 0.49019(16) 0.2306(2) 0.0149(6) Uani 1 1 d . . . 
C11 C 0.4610(3) 0.46222(16) 0.2309(2) 0.0161(6) Uani 1 1 d . . . 
H11 H 0.4741 0.4097 0.2723 0.019 Uiso 1 1 calc R . . 
C11a C 0.3770(3) 0.51523(16) 0.2974(2) 0.0148(6) Uani 1 1 d . . . 
C12 C 0.3465(3) 0.39932(17) 0.4299(2) 0.0256(7) Uani 1 1 d . . . 
H12A H 0.2968 0.3901 0.4925 0.038 Uiso 1 1 calc R . . 
H12B H 0.4536 0.3889 0.4575 0.038 Uiso 1 1 calc R . . 
H12C H 0.3045 0.3633 0.3658 0.038 Uiso 1 1 calc R . . 
C31 C 0.1284(4) 0.67011(19) 0.4762(3) 0.0313(8) Uani 1 1 d . . . 
H31A H 0.0923 0.7169 0.4282 0.047 Uiso 1 1 calc R . . 
H31B H 0.1925 0.6878 0.5495 0.047 Uiso 1 1 calc R . . 
H31C H 0.0432 0.6403 0.4905 0.047 Uiso 1 1 calc R . . 
C51 C 0.3141(3) 0.65751(16) 0.0762(2) 0.0163(6) Uani 1 1 d . . . 
O51 O 0.3684(2) 0.69395(11) 0.00503(15) 0.0212(5) Uani 1 1 d . . . 
C52 C 0.1502(3) 0.64286(18) 0.0543(2) 0.0231(7) Uani 1 1 d . . . 
H52A H 0.1063 0.6805 0.0997 0.035 Uiso 1 1 calc R . . 
H52B H 0.1325 0.5879 0.0764 0.035 Uiso 1 1 calc R . . 
H52C H 0.1042 0.6506 -0.0275 0.035 Uiso 1 1 calc R . . 
C61 C 0.6070(3) 0.70912(16) 0.2882(2) 0.0160(6) Uani 1 1 d . . . 
O61 O 0.7497(2) 0.70908(11) 0.34155(16) 0.0223(5) Uani 1 1 d . . . 
H61 H 0.7652 0.7474 0.3911 0.034 Uiso 1 1 d R . . 
O62 O 0.5169(2) 0.75766(11) 0.30369(18) 0.0268(5) Uani 1 1 d . . . 
C111 C 0.3721(3) 0.44278(17) 0.1067(2) 0.0190(6) Uani 1 1 d . . . 
H11A H 0.3513 0.4933 0.0626 0.023 Uiso 1 1 calc R . . 
H11B H 0.4343 0.4087 0.0691 0.023 Uiso 1 1 calc R . . 
C112 C 0.2253(3) 0.40005(18) 0.1024(3) 0.0273(7) Uani 1 1 d . . . 
H11C H 0.2449 0.3498 0.1457 0.041 Uiso 1 1 calc R . . 
H11D H 0.1752 0.3885 0.0223 0.041 Uiso 1 1 calc R . . 
H11E H 0.1612 0.4344 0.1365 0.041 Uiso 1 1 calc R . . 
 


#=========================================================================
# 10. Molecular Geometry

loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.390(4) . ? 
C1 C11a 1.408(4) . ? 
C1 C12 1.518(4) . ? 
C2 C3 1.396(4) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.384(4) . ? 
C3 C31 1.509(4) . ? 
C4 C4a 1.389(4) . ? 
C4 H4 0.9500 . ? 
C4a C11a 1.396(4) . ? 
C4a N5 1.448(3) . ? 
N5 C51 1.358(3) . ? 
N5 C6 1.466(3) . ? 
C6 C6a 1.529(4) . ? 
C6 C61 1.541(4) . ? 
C6 H6 1.0000 . ? 
C6a C10a 1.400(4) . ? 
C6a C7 1.403(4) . ? 
C7 C8 1.381(4) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.386(4) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.385(4) . ? 
C9 H9 0.9500 . ? 
C10 C10a 1.402(4) . ? 
C10 H10 0.9500 . ? 
C10a C11 1.529(4) . ? 
C11 C11a 1.522(4) . ? 
C11 C111 1.552(4) . ? 
C11 H11 1.0000 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C31 H31A 0.9800 . ? 
C31 H31B 0.9800 . ? 
C31 H31C 0.9800 . ? 
C51 O51 1.246(3) . ? 
C51 C52 1.492(4) . ? 
C52 H52A 0.9800 . ? 
C52 H52B 0.9800 . ? 
C52 H52C 0.9800 . ? 
C61 O62 1.207(3) . ? 
C61 O61 1.319(3) . ? 
O61 H61 0.8604 . ? 
C111 C112 1.521(4) . ? 
C111 H11A 0.9900 . ? 
C111 H11B 0.9900 . ? 
C112 H11C 0.9800 . ? 
C112 H11D 0.9800 . ? 
C112 H11E 0.9800 . ? 

loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C11a 119.3(2) . . ? 
C2 C1 C12 118.6(2) . . ? 
C11a C1 C12 122.1(2) . . ? 
C1 C2 C3 122.8(3) . . ? 
C1 C2 H2 118.6 . . ? 
C3 C2 H2 118.6 . . ? 
C4 C3 C2 117.7(3) . . ? 
C4 C3 C31 120.8(3) . . ? 
C2 C3 C31 121.5(3) . . ? 
C3 C4 C4a 120.4(3) . . ? 
C3 C4 H4 119.8 . . ? 
C4a C4 H4 119.8 . . ? 
C4 C4a C11a 122.3(2) . . ? 
C4 C4a N5 118.9(2) . . ? 
C11a C4a N5 118.8(2) . . ? 
C51 N5 C4a 122.4(2) . . ? 
C51 N5 C6 119.2(2) . . ? 
C4a N5 C6 117.2(2) . . ? 
N5 C6 C6a 115.4(2) . . ? 
N5 C6 C61 108.6(2) . . ? 
C6a C6 C61 116.3(2) . . ? 
N5 C6 H6 105.1 . . ? 
C6a C6 H6 105.1 . . ? 
C61 C6 H6 105.1 . . ? 
C10a C6a C7 118.8(2) . . ? 
C10a C6a C6 126.1(2) . . ? 
C7 C6a C6 115.1(2) . . ? 
C8 C7 C6a 122.1(3) . . ? 
C8 C7 H7 118.9 . . ? 
C6a C7 H7 118.9 . . ? 
C7 C8 C9 119.6(3) . . ? 
C7 C8 H8 120.2 . . ? 
C9 C8 H8 120.2 . . ? 
C10 C9 C8 118.6(3) . . ? 
C10 C9 H9 120.7 . . ? 
C8 C9 H9 120.7 . . ? 
C9 C10 C10a 123.0(3) . . ? 
C9 C10 H10 118.5 . . ? 
C10a C10 H10 118.5 . . ? 
C6a C10a C10 117.8(2) . . ? 
C6a C10a C11 127.3(2) . . ? 
C10 C10a C11 114.8(2) . . ? 
C11a C11 C10a 115.4(2) . . ? 
C11a C11 C111 113.9(2) . . ? 
C10a C11 C111 110.3(2) . . ? 
C11a C11 H11 105.4 . . ? 
C10a C11 H11 105.4 . . ? 
C111 C11 H11 105.4 . . ? 
C4a C11a C1 117.6(2) . . ? 
C4a C11a C11 120.5(2) . . ? 
C1 C11a C11 121.9(2) . . ? 
C1 C12 H12A 109.5 . . ? 
C1 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C1 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
C3 C31 H31A 109.5 . . ? 
C3 C31 H31B 109.5 . . ? 
H31A C31 H31B 109.5 . . ? 
C3 C31 H31C 109.5 . . ? 
H31A C31 H31C 109.5 . . ? 
H31B C31 H31C 109.5 . . ? 
O51 C51 N5 119.8(2) . . ? 
O51 C51 C52 121.1(2) . . ? 
N5 C51 C52 119.0(2) . . ? 
C51 C52 H52A 109.5 . . ? 
C51 C52 H52B 109.5 . . ? 
H52A C52 H52B 109.5 . . ? 
C51 C52 H52C 109.5 . . ? 
H52A C52 H52C 109.5 . . ? 
H52B C52 H52C 109.5 . . ? 
O62 C61 O61 124.8(2) . . ? 
O62 C61 C6 122.0(2) . . ? 
O61 C61 C6 113.1(2) . . ? 
C61 O61 H61 108.4 . . ? 
C112 C111 C11 113.2(2) . . ? 
C112 C111 H11A 108.9 . . ? 
C11 C111 H11A 108.9 . . ? 
C112 C111 H11B 108.9 . . ? 
C11 C111 H11B 108.9 . . ? 
H11A C111 H11B 107.8 . . ? 
C111 C112 H11C 109.5 . . ? 
C111 C112 H11D 109.5 . . ? 
H11C C112 H11D 109.5 . . ? 
C111 C112 H11E 109.5 . . ? 
H11C C112 H11E 109.5 . . ? 
H11D C112 H11E 109.5 . . ? 

loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C11a C1 C2 C3 -0.5(4) . . . . ? 
C12 C1 C2 C3 180.0(3) . . . . ? 
C1 C2 C3 C4 0.0(4) . . . . ? 
C1 C2 C3 C31 179.0(3) . . . . ? 
C2 C3 C4 C4a 0.6(4) . . . . ? 
C31 C3 C4 C4a -178.4(3) . . . . ? 
C3 C4 C4a C11a -0.8(4) . . . . ? 
C3 C4 C4a N5 -179.4(2) . . . . ? 
C4 C4a N5 C51 -62.8(3) . . . . ? 
C11a C4a N5 C51 118.6(3) . . . . ? 
C4 C4a N5 C6 105.2(3) . . . . ? 
C11a C4a N5 C6 -73.5(3) . . . . ? 
C51 N5 C6 C6a -123.6(2) . . . . ? 
C4a N5 C6 C6a 68.0(3) . . . . ? 
C51 N5 C6 C61 103.6(3) . . . . ? 
C4a N5 C6 C61 -64.8(3) . . . . ? 
N5 C6 C6a C10a -11.2(4) . . . . ? 
C61 C6 C6a C10a 117.9(3) . . . . ? 
N5 C6 C6a C7 166.2(2) . . . . ? 
C61 C6 C6a C7 -64.7(3) . . . . ? 
C10a C6a C7 C8 -1.8(4) . . . . ? 
C6 C6a C7 C8 -179.4(2) . . . . ? 
C6a C7 C8 C9 1.6(4) . . . . ? 
C7 C8 C9 C10 0.1(4) . . . . ? 
C8 C9 C10 C10a -1.6(4) . . . . ? 
C7 C6a C10a C10 0.4(4) . . . . ? 
C6 C6a C10a C10 177.6(2) . . . . ? 
C7 C6a C10a C11 -176.1(2) . . . . ? 
C6 C6a C10a C11 1.1(4) . . . . ? 
C9 C10 C10a C6a 1.4(4) . . . . ? 
C9 C10 C10a C11 178.3(2) . . . . ? 
C6a C10a C11 C11a -43.6(4) . . . . ? 
C10 C10a C11 C11a 139.8(2) . . . . ? 
C6a C10a C11 C111 87.1(3) . . . . ? 
C10 C10a C11 C111 -89.4(3) . . . . ? 
C4 C4a C11a C1 0.4(4) . . . . ? 
N5 C4a C11a C1 179.0(2) . . . . ? 
C4 C4a C11a C11 179.3(2) . . . . ? 
N5 C4a C11a C11 -2.1(4) . . . . ? 
C2 C1 C11a C4a 0.2(4) . . . . ? 
C12 C1 C11a C4a 179.8(2) . . . . ? 
C2 C1 C11a C11 -178.6(2) . . . . ? 
C12 C1 C11a C11 0.9(4) . . . . ? 
C10a C11 C11a C4a 59.8(3) . . . . ? 
C111 C11 C11a C4a -69.3(3) . . . . ? 
C10a C11 C11a C1 -121.4(3) . . . . ? 
C111 C11 C11a C1 109.5(3) . . . . ? 
C4a N5 C51 O51 170.9(2) . . . . ? 
C6 N5 C51 O51 3.1(4) . . . . ? 
C4a N5 C51 C52 -11.5(4) . . . . ? 
C6 N5 C51 C52 -179.2(2) . . . . ? 
N5 C6 C61 O62 -24.6(3) . . . . ? 
C6a C6 C61 O62 -156.9(2) . . . . ? 
N5 C6 C61 O61 159.0(2) . . . . ? 
C6a C6 C61 O61 26.7(3) . . . . ? 
C11a C11 C111 C112 -59.2(3) . . . . ? 
C10a C11 C111 C112 169.2(2) . . . . ? 


loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
 _geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
# D  H  A             D-H   H...A  D...A    D-H...A  symm  publ
# -  -  -             ---   -----  -----    -------  ----  ----
O61 H61 O51           0.86  1.76   2.575(3)  156     4_676  no
C9  H9  O62           0.95  2.50   3.329(3)  145     2_645  no
C8  H8  '<i>Cg</i>1'  0.95  2.75   3.569(3)  144     1_655  no

_iucr_geom_hbonds_special_details
;
Cg1 represents the centroid of the C1--C4/C4a/C11a ring.
;

#======================================================================



#======================================================================
#                         END of CIF
#======================================================================

# start Validation Reply Form
_vrf_PUBL005_GLOBAL
;
PROBLEM: _publ_contact_author_email, _publ_contact_author_fax and
RESPONSE: Example CIF
;
# end Validation Reply Form
