##############################################################################
###    CIF submission form for molecular structure report (Acta Cryst. C)  ###
###                                               Version: 7 October 1991  ###
##############################################################################

# This is an electronic "form" for submitting a structural paper to Acta Cryst.
# Section C as a Crystallographic Information File. Full details of the format
# of such files are given in the paper "The Crystallographic Information File
# (CIF): a New Standard Archive File for Crystallography" by S. R. Hall, F. H.
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. An example of a
# completed CIF form may be obtained by sending the one-line request 
#      'send example.cif'
# to sendcif@iucr.ac.uk. Queries or requests for further information should be
# directed to teched@iucr.ac.uk.
#
# Note that all fields should be numeric or character type EXCEPT those which
# are flagged as 'text' - free-form text of any length may be included in
# these latter fields provided the text block begins and ends with a semicolon
# as the first character of a new line. . Note also that the query marks
# '?' are significant as placeholders, and should not be deleted where a data
# item is not given, UNLESS the accompanying data name is also deleted.
# Lines should not exceed 80 characters in length.

#============================================================================== 
data_global
#==============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author           # Name and address of author for correspondence
;
      Dr Anthony C. Willis
      Research School of Chemistry
      Australian National University
      GPO Box 4
      Canberra, A.C.T.
      Australia    2601
;
_publ_contact_author_phone        '616 249 4109'
_publ_contact_author_fax          '616 249 0750'
_publ_contact_author_email        willis@RSC3.anu.oz.au
   
_publ_requested_journal           'Acta Crystallographica C'
_publ_requested_coeditor_name     ?

_publ_contact_letter
;
     Please consider this CIF submission for publication as a New Structure
     paper in Acta Crystallographica Section C.  The figures, chemical
     structure diagram (scheme), Transfer of Copyright Agreement form and 
     structure factors will be sent on receipt of your acknowledgement 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_coeditor_notes
; ?
;

_journal_techeditor_code          ?
_journal_techeditor_notes
; ?
;

_journal_coden_ASTM               ?
_journal_name_full                ?
_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
;
trans-3-Benzoyl-2-(tert-butyl)-4-(iso-butyl)-1,3-oxazolidin-5-one
;

# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.

loop_
	_publ_author_name
	_publ_author_address
'Willis, Anthony C.'            #<--'Last name, first name' 
;     Research School of Chemistry 
      Australian National University
      GPO Box 4
      Canberra, A.C.T.
      Australia    2601
; 
     'Beckwith, Athelstan L.J.'
;     Research School of Chemistry
      Australian National University
      GPO Box 4
      Canberra, A.C.T.
      Australia    2601
;
     'Tozer, Matthew J.'
;     Research School of Chemistry
      Australian National University
      GPO Box 4
      Canberra, A.C.T.
      Australia    2601
;
 
#==============================================================================

# 4. TEXT

_publ_section_abstract
;
The oxazolidinone ring is a shallow envelope conformation with the 
tert-butyl and iso-butyl groups occupying trans-positions with respect to 
the ring.  The angles at the N atom sum to 356.2°, indicating a 
very small degree of pyramidalization at this atom.  This is consistent
with electron delocalization between the N atom and the
carbonyl centre [N--C=O = 1.374(3)Å].
;
_publ_section_comment
;
The structure of the title compound was undertaken to establish
whether a sec-butyl group would be formed cis or trans to the tert-butyl group 
as part of a study of diastereoselectivities of free radical reactions.  Details
of the synthetic work will be published elsewhere (Beckwith, Chai & Tozer, 
1991).

The tert-butyl and iso-butyl groups are trans, as expected 
from nmr evidence.  The oxazolidinone ring is in an envelope conformation 
with C(5) the out-of-plane atom.  The angle between the least-squares plane 
through atoms O(1), C(2), C(3) and N(4) and the plane of N(4), C(5) and O(1)
is 10.9(2)°.  Intra-annular torsion angles (starting with 
C(5)-O(1)-C(2)-C(3) and proceeding around the ring) are 9.5, -2.3, -5.4, 10.7
and -12.3(3)°.  A search of the January 1990 Version of the Cambridge 
Structure Database (Allen, Kennard & Taylor, 1983) revealed three structure
determinations with 1,3-oxazolidin-5-one fragments (Seebach, Boes, Naef & 
Schweizer 1983, Karady, Amato & Weinstock 1984, Weber, Aeschimann, Maetzke & 
Seebach 1986).  Bond lengths and angles in these compounds are comparable 
with those in the present study; the magnitudes of their respective maximum 
intra-annular torsion angle are 10.2, 1.9 and 10.2°.  Diagrams and 
most calculations were performed with the Xtal3.0 package (Hall & Stewart, 
1990), as was the generation of the Crystallographic Information File used for 
the submission of this paper.
;

_publ_section_experimental
; ?
;

_publ_section_references
;
Allen, F.H., Kennard, O. and Taylor, R. (1983) Accounts Chem. Res., 16, 
146-152.  

Beckwith, A.L.J., Chai, C.L.L. & Tozer, M.J. (1991)  manuscript 
in preparation. 
 
Hall, S.R. and Stewart, J.M. (1990) Eds. Xtal3.0 Reference Manual. University
     of Western Australia and University of Maryland.
 
Karady, S., Amato, J.S. & Weinstock, L.M. (1984).  Tetrahedron Lett.,25,
4337-4340.
 
McLaughlin, G.M. (1983).  PWREDU. Program for data reduction for Philips 
PW1100/20 diffractometer.  Australian National Univ., Canberra.
 
Seebach, D., Boes,M., Naef, W.B. & Schweizer, W.B. (1983). J Am. Chem. Soc.,
105,5390-5398.
 
Sheldrick, G.M. (1976).  SHELX76. Program for crystal structure 
determination.  Univ. of Cambridge, England.
 
Sheldrick, G.M. (1985).  SHELXS86. Program for the solution of crystal
structures.  Univ. of Gottingen, Federal Republic of Germany.
 
Weber, T., Aeschimann, R., Maetzke, T. & Seebach, D. (1986) Helv. Chim. Acta,
69,1365-1377.
;
_publ_section_figure_captions
;
View of C₁₈H₂₅O₃N showing the labelling of the non-H atoms.  Thermal
ellipsoids are shown at 50% probability levels; H atoms are drawn as
small circles of arbitrary radius.
;
_publ_section_acknowledgements
; ?
;

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

# If more than one structure is reported, sections 5-10 should be filled in 
# per structure. For each data set, replace the '?' in the data_? line below
# by a unique identifier.

data_TOZ

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

# 5. CHEMICAL DATA

_chemical_name_systematic
;
trans-3-Benzoyl-2-(tert-butyl)-4-(iso-butyl)-1,3-oxazolidin-5-one
;
_chemical_name_common             ?
_chemical_formula_moiety          'C18 H25 N O3'
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C18 H25 N O3'
_chemical_formula_weight          303.40
_chemical_melting_point           ?
_chemical_compound_source         ?

loop_
     _atom_type_symbol
     _atom_type_description
     _atom_type_scat_dispersion_real
     _atom_type_scat_dispersion_imag
     _atom_type_scat_source
  C  ?  .017  .009  International_Tables_Vol_IV_Table_2.3.1
  H  ?  0  0  International_Tables_Vol_IV_Table_2.3.1
  O  ?  .047  .032  International_Tables_Vol_IV_Table_2.3.1
  N  ?  .029  .018  International_Tables_Vol_IV_Table_2.3.1

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

# 6. CRYSTAL DATA

_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    'P 21 21 21'
_symmetry_space_group_name_Hall   'P 2ac 2ab'
loop_
        _symmetry_equiv_pos_as_xyz
       'x,y,z'
       1/2-x,-y,1/2+z
       1/2+x,1/2-y,-z
       -x,1/2+y,1/2-z

_cell_length_a                    5.959(1)
_cell_length_b                    14.956(1)
_cell_length_c                    19.737(3)
_cell_angle_alpha                 90.0
_cell_angle_beta                  90.0
_cell_angle_gamma                 90.0
_cell_volume                      1759.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     293
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       25
_cell_measurement_theta_max       31
_cell_special_details
; ?
;

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.32
_exptl_crystal_size_mid           0.27
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       1.146
_exptl_crystal_density_diffrn     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              656
_exptl_absorpt_coefficient_mu     0.59
_exptl_absorpt_correction_type    'shelx76 gaussian'
_exptl_absorpt_correction_T_min   .933
_exptl_absorpt_correction_T_max   .824

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

# 7. EXPERIMENTAL DATA

_exptl_special_details
; ?
;

_diffrn_ambient_temperature       293
_diffrn_radiation_wavelength      1.5418
_diffrn_radiation_type            'Copper K\a'
_diffrn_radiation_source          xray_tube

_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device        'Philips PW1100/20 diffractometer'
_diffrn_measurement_method        θ/2θ

_diffrn_standards_number          3
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   120
_diffrn_standards_decay_%         0
loop_
        _diffrn_standard_refln_index_h
        _diffrn_standard_refln_index_k
        _diffrn_standard_refln_index_l
  3 2 4
  1 9 1
  3 0 10

_diffrn_reflns_number             1592
_diffrn_reflns_av_R_equivalents   0
_diffrn_reflns_av_sigmaI/netI     .027
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        0
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.71
_diffrn_reflns_theta_max          61.97

_diffrn_reflns_reduction_process  ?

_reflns_number_total              ?
_reflns_number_observed           ?
_reflns_observed_criterion        ?

_computing_data_collection         'Philips PW1100/20 software 1976'
_computing_cell_refinement         xtal_LATCON
_computing_data_reduction          'pwredu, xtal_ADDREF_SORTRF'
_computing_structure_solution      shelxs86
_computing_structure_refinement    'shelx76, xtal_CRYLSQ'
_computing_molecular_graphics     ?
_computing_publication_material   xtal_BONDLA_CIFIO

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

# 8. REFINEMENT DATA

_refine_special_details
;
sfls: F    calc weight    full matrix
;

_refine_ls_structure_factor_coef  F
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       '1/(\s^2^(F)+0.0004F^2^)'
_refine_ls_hydrogen_treatment     'refxyz except H332B noref'
_refine_ls_extinction_method      Zachariasen
_refine_ls_extinction_coef        3514(42)
_refine_ls_extinction_expression 
      'equ(22) p292 "Crystallographic Computing" (1970)'
_refine_ls_abs_structure_details  
;   The absolute configuration was assigned to agree with the known chirality 
    at C(3) arising from its precursor l-leucine.
;
_refine_ls_abs_structure_Flack    0
_refine_ls_number_reflns          1408
_refine_ls_number_parameters      272
_refine_ls_number_restraints      0
_refine_ls_number_constraints     0
_refine_ls_R_factor_all           .038
_refine_ls_R_factor_obs           .034
_refine_ls_wR_factor_all          .044
_refine_ls_wR_factor_obs          .042
_refine_ls_goodness_of_fit_all    1.462
_refine_ls_goodness_of_fit_obs    1.515
_refine_ls_shift/esd_max          .535
_refine_ls_shift/esd_mean         .044
_refine_diff_density_max          .131
_refine_diff_density_min          -.108

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

# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
        _atom_site_label 
        _atom_site_fract_x 
        _atom_site_fract_y
        _atom_site_fract_z
        _atom_site_U_iso_or_equiv                                          
        _atom_site_thermal_displace_type
        _atom_site_calc_flag        
        _atom_site_calc_attached_atom 
        _atom_site_type_symbol       
  O1  .4154(4)  .5699(1)  .3026(0)  .060(1)  Uij  ?  ?  O
  C2  .5630(5)  .5087(2)  .3246(1)  .060(2)  Uij  ?  ?  C
  C3  .5350(5)  .4920(2)  .3997(1)  .048(1)  Uij  ?  ?  C
  N4  .3570(3)  .5558(1)  .4167(0)  .039(1)  Uij  ?  ?  N
  C5  .3000(5)  .6122(2)  .3581(1)  .045(1)  Uij  ?  ?  C
  O21  .6958(5)  .4738(2)  .2874(1)  .090(2)  Uij  ?  ?  O
  C31  .4869(6)  .3929(2)  .4143(2)  .059(2)  Uij  ?  ?  C
  C32  .2552(7)  .3558(2)  .3953(2)  .073(2)  Uij  ?  ?  C
  C321  .209(1)  .3542(4)  .3211(3)  .111(4)  Uij  ?  ?  C
  C322  .230(1)  .2626(3)  .4264(3)  .149(5)  Uij  ?  ?  C
  C41  .2034(4)  .5476(2)  .4682(1)  .041(1)  Uij  ?  ?  C
  O41  .0124(3)  .5776(1)  .4624(0)  .054(1)  Uij  ?  ?  O
  C411  .2826(4)  .5093(2)  .5334(1)  .043(1)  Uij  ?  ?  C
  C412  .1315(5)  .4613(2)  .5725(1)  .064(2)  Uij  ?  ?  C
  C413  .1914(7)  .4324(3)  .6366(2)  .086(2)  Uij  ?  ?  C
  C414  .3987(6)  .4522(3)  .6620(1)  .078(2)  Uij  ?  ?  C
  C415  .5494(6)  .4997(2)  .6241(1)  .065(2)  Uij  ?  ?  C
  C416  .4920(5)  .5279(2)  .5594(1)  .053(2)  Uij  ?  ?  C
  C51  .3745(5)  .7097(2)  .3634(1)  .052(2)  Uij  ?  ?  C
  C511  .6299(6)  .7166(3)  .3669(2)  .072(2)  Uij  ?  ?  C
  C512  .2881(8)  .7581(3)  .3000(2)  .079(2)  Uij  ?  ?  C
  C513  .2757(7)  .7522(2)  .4267(2)  .068(2)  Uij  ?  ?  C
  H3  .679(5)  .510(2)  .422(1)  .06000  Uiso  ?  ?  H
  H5  .135(5)  .608(2)  .350(1)  .06000  Uiso  ?  ?  H
  H31A  .507(5)  .381(2)  .461(2)  .07000  Uiso  ?  ?  H
  H31B  .593(6)  .357(2)  .390(2)  .07000  Uiso  ?  ?  H
  H32  .129(6)  .401(3)  .417(2)  .09000  Uiso  ?  ?  H
  H321A  .330(9)  .311(4)  .306(3)  .14000  Uiso  ?  ?  H
  H321B  .22(1)  .415(4)  .298(2)  .14000  Uiso  ?  ?  H
  H321C  .04(1)  .318(3)  .320(2)  .14000  Uiso  ?  ?  H
  H322A  .25(1)  .272(4)  .475(3)  .19000  Uiso  ?  ?  H
  H322B  .34976  .22118  .40954  .19000  Uiso  calc  C322 H
  H322C  .08(1)  .234(4)  .397(3)  .19000  Uiso  ?  ?  H
  H412  -.007(6)  .447(2)  .552(2)  .08000  Uiso  ?  ?  H
  H413  .096(7)  .392(3)  .661(2)  .11000  Uiso  ?  ?  H
  H414  .447(7)  .433(2)  .708(2)  .10000  Uiso  ?  ?  H
  H415  .722(6)  .521(2)  .641(2)  .08000  Uiso  ?  ?  H
  H416  .588(5)  .564(2)  .535(1)  .07000  Uiso  ?  ?  H
  H511A  .683(7)  .692(2)  .322(2)  .09000  Uiso  ?  ?  H
  H511B  .689(6)  .681(2)  .408(2)  .09000  Uiso  ?  ?  H
  H511C  .678(7)  .781(3)  .372(2)  .09000  Uiso  ?  ?  H
  H512A  .143(8)  .759(3)  .302(2)  .10000  Uiso  ?  ?  H
  H512B  .345(7)  .726(3)  .258(2)  .10000  Uiso  ?  ?  H
  H512C  .361(7)  .820(3)  .302(2)  .10000  Uiso  ?  ?  H
  H513A  .337(6)  .717(2)  .469(2)  .09000  Uiso  ?  ?  H
  H513B  .115(7)  .757(3)  .426(2)  .09000  Uiso  ?  ?  H
  H513C  .329(6)  .817(2)  .430(2)  .09000  Uiso  ?  ?  H

                                    

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

# 10. MOLECULAR GEOMETRY

_geom_special_details        ?
           
loop_
        _geom_bond_atom_site_label_1  
        _geom_bond_atom_site_label_2 
        _geom_bond_distance       
        _geom_bond_site_symmetry_1  
        _geom_bond_site_symmetry_2 
        _geom_bond_publ_flag       
  O1  C2  1.342(4)  .  .  yes
  O1  C5  1.439(3)  .  .  yes
  C2  C3  1.512(4)  .  .  yes
  C2  O21  1.199(4)  .  .  yes
  C3  N4  1.465(3)  .  .  yes
  C3  C31  1.537(4)  .  .  yes
  C3  H3  1.00(3)  .  .  ?
  N4  C5  1.472(3)  .  .  yes
  N4  C41  1.374(3)  .  .  yes
  C5  C51  1.528(4)  .  .  yes
  C5  H5  1.00(3)  .  .  ?
  C31  C32  1.535(5)  .  .  yes
  C31  H31A  .95(3)  .  .  ?
  C31  H31B  .96(3)  .  .  ?
  C32  C321  1.490(7)  .  .  yes
  C32  C322  1.531(6)  .  .  yes
  C32  H32  1.10(4)  .  .  ?
  C321  H321A  1.01(5)  .  .  ?
  C321  H321B  1.02(5)  .  .  ?
  C321  H321C  1.14(6)  .  .  ?
  C322  H322A  .98(5)  .  .  ?
  C322  H322B  1.002  .  .  ?
  C322  H322C  1.15(7)  .  .  ?
  C41  O41  1.229(3)  .  .  yes
  C41  C411  1.485(3)  .  .  yes
  C411  C412  1.386(4)  .  .  yes
  C411  C416  1.378(4)  .  .  yes
  C412  C413  1.383(4)  .  .  yes
  C412  H412  .94(4)  .  .  ?
  C413  C414  1.366(5)  .  .  yes
  C413  H413  .96(4)  .  .  ?
  C414  C415  1.368(5)  .  .  yes
  C414  H414  1.00(4)  .  .  ?
  C415  C416  1.387(4)  .  .  yes
  C415  H415  1.12(4)  .  .  ?
  C416  H416  .93(3)  .  .  ?
  C51  C511  1.527(5)  .  .  yes
  C51  C512  1.533(5)  .  .  yes
  C51  C513  1.520(5)  .  .  yes
  C511  H511A  1.00(4)  .  .  ?
  C511  H511B  1.03(4)  .  .  ?
  C511  H511C  1.01(4)  .  .  ?
  C512  H512A  .87(5)  .  .  ?
  C512  H512B  1.03(4)  .  .  ?
  C512  H512C  1.03(4)  .  .  ?
  C513  H513A  1.06(3)  .  .  ?
  C513  H513B  .96(4)  .  .  ?
  C513  H513C  1.02(4)  .  .  ?
                                   
loop_
        _geom_contact_atom_site_label_1 
        _geom_contact_atom_site_label_2
        _geom_contact_distance      
        _geom_contact_site_symmetry_1 
        _geom_contact_site_symmetry_2
        _geom_contact_publ_flag 
       ?   ?   ?   ?   ?   ?  
                                    
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_2  
        _geom_angle_site_symmetry_3 
        _geom_angle_publ_flag       
  C2  O1  C5  111.6(2)  .  .  .  yes
  O1  C2  C3  110.9(2)  .  .  .  yes
  O1  C2  O21  122.2(3)  .  .  .  yes
  C3  C2  O21  127.0(3)  .  .  .  yes
  C2  C3  N4  101.3(2)  .  .  .  yes
  C2  C3  C31  111.3(2)  .  .  .  yes
  C2  C3  H3  107(1)  .  .  .  ?
  N4  C3  C31  116.7(2)  .  .  .  yes
  N4  C3  H3  110(1)  .  .  .  ?
  C31  C3  H3  110(1)  .  .  .  ?
  C3  N4  C5  111.2(2)  .  .  .  yes
  C3  N4  C41  126.4(2)  .  .  .  yes
  C5  N4  C41  118.6(2)  .  .  .  yes
  O1  C5  N4  103.6(2)  .  .  .  yes
  O1  C5  C51  109.4(2)  .  .  .  yes
  O1  C5  H5  109(1)  .  .  .  ?
  N4  C5  C51  115.3(2)  .  .  .  yes
  N4  C5  H5  109(1)  .  .  .  ?
  C51  C5  H5  111(1)  .  .  .  ?
  C3  C31  C32  118.1(3)  .  .  .  yes
  C3  C31  H31A  110(1)  .  .  .  ?
  C3  C31  H31B  109(1)  .  .  .  ?
  C32  C31  H31A  107(1)  .  .  .  ?
  C32  C31  H31B  105(1)  .  .  .  ?
  H31A  C31  H31B  108(1)  .  .  .  ?
  C31  C32  C321  114.5(4)  .  .  .  yes
  C31  C32  C322  108.6(4)  .  .  .  yes
  C31  C32  H32  107(1)  .  .  .  ?
  C321  C32  C322  111.2(4)  .  .  .  yes
  C321  C32  H32  105(1)  .  .  .  ?
  C322  C32  H32  110(1)  .  .  .  ?
  C32  C321  H321A  99(1)  .  .  .  ?
  C32  C321  H321B  114(1)  .  .  .  ?
  C32  C321  H321C  101(1)  .  .  .  ?
  H321A  C321  H321B  113(1)  .  .  .  ?
  H321A  C321  H321C  109(1)  .  .  .  ?
  H321B  C321  H321C  119(1)  .  .  .  ?
  C32  C322  H322A  104(1)  .  .  .  ?
  C32  C322  H322B  111.1  .  .  .  ?
  C32  C322  H322C  103(1)  .  .  .  ?
  H322A  C322  H322B  108  .  .  .  ?
  H322A  C322  H322C  131(1)  .  .  .  ?
  H322B  C322  H322C  99  .  .  .  ?
  N4  C41  O41  121.0(2)  .  .  .  yes
  N4  C41  C411  117.6(2)  .  .  .  yes
  O41  C41  C411  121.1(2)  .  .  .  yes
  C41  C411  C412  118.4(2)  .  .  .  yes
  C41  C411  C416  122.2(2)  .  .  .  yes
  C412  C411  C416  119.0(2)  .  .  .  yes
  C411  C412  C413  120.3(3)  .  .  .  yes
  C411  C412  H412  117(1)  .  .  .  ?
  C413  C412  H412  123(1)  .  .  .  ?
  C412  C413  C414  120.1(3)  .  .  .  yes
  C412  C413  H413  120(1)  .  .  .  ?
  C414  C413  H413  119(1)  .  .  .  ?
  C413  C414  C415  120.4(3)  .  .  .  yes
  C413  C414  H414  122(1)  .  .  .  ?
  C415  C414  H414  117(1)  .  .  .  ?
  C414  C415  C416  120.0(3)  .  .  .  yes
  C414  C415  H415  126(1)  .  .  .  ?
  C416  C415  H415  114(1)  .  .  .  ?
  C411  C416  C415  120.4(3)  .  .  .  yes
  C411  C416  H416  119(1)  .  .  .  ?
  C415  C416  H416  120(1)  .  .  .  ?
  C5  C51  C511  110.9(3)  .  .  .  yes
  C5  C51  C512  107.3(3)  .  .  .  yes
  C5  C51  C513  110.0(2)  .  .  .  yes
  C511  C51  C512  109.9(3)  .  .  .  yes
  C511  C51  C513  108.7(3)  .  .  .  yes
  C512  C51  C513  110.0(3)  .  .  .  yes
  C51  C511  H511A  104(1)  .  .  .  ?
  C51  C511  H511B  110(1)  .  .  .  ?
  C51  C511  H511C  111(1)  .  .  .  ?
  H511A  C511  H511B  113(1)  .  .  .  ?
  H511A  C511  H511C  111(1)  .  .  .  ?
  H511B  C511  H511C  108(1)  .  .  .  ?
  C51  C512  H512A  108(1)  .  .  .  ?
  C51  C512  H512B  109(1)  .  .  .  ?
  C51  C512  H512C  105(1)  .  .  .  ?
  H512A  C512  H512B  112(1)  .  .  .  ?
  H512A  C512  H512C  114(1)  .  .  .  ?
  H512B  C512  H512C  108(1)  .  .  .  ?
  C51  C513  H513A  108(1)  .  .  .  ?
  C51  C513  H513B  114(1)  .  .  .  ?
  C51  C513  H513C  109(1)  .  .  .  ?
  H513A  C513  H513B  113(1)  .  .  .  ?
  H513A  C513  H513C  108(1)  .  .  .  ?
  H513B  C513  H513C  104(1)  .  .  .  ?
                                    
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  
  C5  O1  C2  C3  9.5(3)  .  .  .  .  ?
  C5  O1  C2  O21  -170.6(3)  .  .  .  .  ?
  C2  O1  C5  N4  -12.3(3)  .  .  .  .  ?
  C2  O1  C5  C51  111.2(3)  .  .  .  .  ?
  C2  O1  C5  H5  -128(1)  .  .  .  .  ?
  O1  C2  C3  N4  -2.3(3)  .  .  .  .  ?
  O1  C2  C3  C31  122.5(3)  .  .  .  .  ?
  O1  C2  C3  H3  -118(1)  .  .  .  .  ?
  O21  C2  C3  N4  177.7(3)  .  .  .  .  ?
  O21  C2  C3  C31  -57.5(4)  .  .  .  .  ?
  O21  C2  C3  H3  62(1)  .  .  .  .  ?
  C2  C3  N4  C5  -5.4(3)  .  .  .  .  ?
  C2  C3  N4  C41  152.1(2)  .  .  .  .  ?
  C31  C3  N4  C5  -126.5(2)  .  .  .  .  ?
  C31  C3  N4  C41  31.0(3)  .  .  .  .  ?
  H3  C3  N4  C5  108(1)  .  .  .  .  ?
  H3  C3  N4  C41  -95(1)  .  .  .  .  ?
  C2  C3  C31  C32  -72.1(4)  .  .  .  .  ?
  C2  C3  C31  H31A  166(1)  .  .  .  .  ?
  C2  C3  C31  H31B  48(1)  .  .  .  .  ?
  N4  C3  C31  C32  43.6(4)  .  .  .  .  ?
  N4  C3  C31  H31A  -79(1)  .  .  .  .  ?
  N4  C3  C31  H31B  164(1)  .  .  .  .  ?
  H3  C3  C31  C32  170(1)  .  .  .  .  ?
  H3  C3  C31  H31A  48(1)  .  .  .  .  ?
  H3  C3  C31  H31B  -70(1)  .  .  .  .  ?
  C3  N4  C5  O1  10.7(3)  .  .  .  .  ?
  C3  N4  C5  C51  -108.9(2)  .  .  .  .  ?
  C3  N4  C5  H5  126(1)  .  .  .  .  ?
  C41  N4  C5  O1  -148.8(2)  .  .  .  .  ?
  C41  N4  C5  C51  91.7(3)  .  .  .  .  ?
  C41  N4  C5  H5  -33(1)  .  .  .  .  ?
  C3  N4  C41  O41  -147.4(2)  .  .  .  .  ?
  C3  N4  C41  C411  38.4(3)  .  .  .  .  ?
  C5  N4  C41  O41  8.6(3)  .  .  .  .  ?
  C5  N4  C41  C411  -165.6(2)  .  .  .  .  ?
  O1  C5  C51  C511  -52.9(3)  .  .  .  .  ?
  O1  C5  C51  C512  67.1(3)  .  .  .  .  ?
  O1  C5  C51  C513  -173.2(2)  .  .  .  .  ?
  N4  C5  C51  C511  63.3(3)  .  .  .  .  ?
  N4  C5  C51  C512  -176.7(3)  .  .  .  .  ?
  N4  C5  C51  C513  -57.0(3)  .  .  .  .  ?
  H5  C5  C51  C511  -173(1)  .  .  .  .  ?
  H5  C5  C51  C512  -53(1)  .  .  .  .  ?
  H5  C5  C51  C513  67(1)  .  .  .  .  ?
  C3  C31  C32  C321  65.8(4)  .  .  .  .  ?
  C3  C31  C32  C322  -169.3(4)  .  .  .  .  ?
  C3  C31  C32  H32  -50(1)  .  .  .  .  ?
  H31A  C31  C32  C321  -171(1)  .  .  .  .  ?
  H31A  C31  C32  C322  -46(1)  .  .  .  .  ?
  H31A  C31  C32  H32  73(1)  .  .  .  .  ?
  H31B  C31  C32  C321  -56(1)  .  .  .  .  ?
  H31B  C31  C32  C322  69(1)  .  .  .  .  ?
  H31B  C31  C32  H32  -172(1)  .  .  .  .  ?
  C31  C32  C321  H321A  63(1)  .  .  .  .  ?
  C31  C32  C321  H321B  -57(1)  .  .  .  .  ?
  C31  C32  C321  H321C  174(1)  .  .  .  .  ?
  C322  C32  C321  H321A  -61(1)  .  .  .  .  ?
  C322  C32  C321  H321B  179(1)  .  .  .  .  ?
  C322  C32  C321  H321C  51(1)  .  .  .  .  ?
  H32  C32  C321  H321A  -180(1)  .  .  .  .  ?
  H32  C32  C321  H321B  60(1)  .  .  .  .  ?
  H32  C32  C321  H321C  -68(1)  .  .  .  .  ?
  C31  C32  C322  H322A  57(1)  .  .  .  .  ?
  C31  C32  C322  H322B  -59.3  .  .  .  .  ?
  C31  C32  C322  H322C  -164(1)  .  .  .  .  ?
  C321  C32  C322  H322A  -176(1)  .  .  .  .  ?
  C321  C32  C322  H322B  67.6  .  .  .  .  ?
  C321  C32  C322  H322C  -38(1)  .  .  .  .  ?
  H32  C32  C322  H322A  -61(1)  .  .  .  .  ?
  H32  C32  C322  H322B  -176  .  .  .  .  ?
  H32  C32  C322  H322C  78(1)  .  .  .  .  ?
  N4  C41  C411  C412  -149.4(3)  .  .  .  .  ?
  N4  C41  C411  C416  37.8(4)  .  .  .  .  ?
  O41  C41  C411  C412  36.4(4)  .  .  .  .  ?
  O41  C41  C411  C416  -136.4(3)  .  .  .  .  ?
  C41  C411  C412  C413  -173.4(3)  .  .  .  .  ?
  C41  C411  C412  H412  10(1)  .  .  .  .  ?
  C416  C411  C412  C413  -.4(5)  .  .  .  .  ?
  C416  C411  C412  H412  -177(1)  .  .  .  .  ?
  C41  C411  C416  C415  172.2(3)  .  .  .  .  ?
  C41  C411  C416  H416  -1(1)  .  .  .  .  ?
  C412  C411  C416  C415  -.5(4)  .  .  .  .  ?
  C412  C411  C416  H416  -174(1)  .  .  .  .  ?
  C411  C412  C413  C414  1.0(6)  .  .  .  .  ?
  C411  C412  C413  H413  -171(1)  .  .  .  .  ?
  H412  C412  C413  C414  177(1)  .  .  .  .  ?
  H412  C412  C413  H413  5(1)  .  .  .  .  ?
  C412  C413  C414  C415  -.8(6)  .  .  .  .  ?
  C412  C413  C414  H414  179(1)  .  .  .  .  ?
  H413  C413  C414  C415  171(1)  .  .  .  .  ?
  H413  C413  C414  H414  -9(1)  .  .  .  .  ?
  C413  C414  C415  C416  -.1(6)  .  .  .  .  ?
  C413  C414  C415  H415  178(1)  .  .  .  .  ?
  H414  C414  C415  C416  -180(1)  .  .  .  .  ?
  H414  C414  C415  H415  -1(1)  .  .  .  .  ?
  C414  C415  C416  C411  .8(5)  .  .  .  .  ?
  C414  C415  C416  H416  174(1)  .  .  .  .  ?
  H415  C415  C416  C411  -178(1)  .  .  .  .  ?
  H415  C415  C416  H416  -4(1)  .  .  .  .  ?
  C5  C51  C511  H511A  63(1)  .  .  .  .  ?
  C5  C51  C511  H511B  -59(1)  .  .  .  .  ?
  C5  C51  C511  H511C  -178(1)  .  .  .  .  ?
  C512  C51  C511  H511A  -55(1)  .  .  .  .  ?
  C512  C51  C511  H511B  -177(1)  .  .  .  .  ?
  C512  C51  C511  H511C  64(1)  .  .  .  .  ?
  C513  C51  C511  H511A  -176(1)  .  .  .  .  ?
  C513  C51  C511  H511B  62(1)  .  .  .  .  ?
  C513  C51  C511  H511C  -57(1)  .  .  .  .  ?
  C5  C51  C512  H512A  66(1)  .  .  .  .  ?
  C5  C51  C512  H512B  -56(1)  .  .  .  .  ?
  C5  C51  C512  H512C  -172(1)  .  .  .  .  ?
  C511  C51  C512  H512A  -173(1)  .  .  .  .  ?
  C511  C51  C512  H512B  65(1)  .  .  .  .  ?
  C511  C51  C512  H512C  -51(1)  .  .  .  .  ?
  C513  C51  C512  H512A  -53(1)  .  .  .  .  ?
  C513  C51  C512  H512B  -175(1)  .  .  .  .  ?
  C513  C51  C512  H512C  69(1)  .  .  .  .  ?
  C5  C51  C513  H513A  61(1)  .  .  .  .  ?
  C5  C51  C513  H513B  -65(1)  .  .  .  .  ?
  C5  C51  C513  H513C  179(1)  .  .  .  .  ?
  C511  C51  C513  H513A  -60(1)  .  .  .  .  ?
  C511  C51  C513  H513B  173(1)  .  .  .  .  ?
  C511  C51  C513  H513C  57(1)  .  .  .  .  ?
  C512  C51  C513  H513A  179(1)  .  .  .  .  ?
  C512  C51  C513  H513B  53(1)  .  .  .  .  ?
  C512  C51  C513  H513C  -63(1)  .  .  .  .  ?


#==============================================================================
# Additional structures (sections 5-10 and associated data_? identifiers)
# may be added at this point.
#==============================================================================

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set.
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./                 

