#########################################################################
#									#
#		THIS IS AN EXAMPLE OF A CIF 				#
#		PRODUCED BY THE OLEX2 PROGRAM				#
#									#
#       Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., 		#
#       Howard, J. A. K. & Puschmann, H. (2009). J. Appl. 		#
#       Cryst. 42, 339-341.						#
#									#
#########################################################################

data_global

_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_journal_date_recd_electronic     ?
_journal_date_accepted            ?
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     ?
_journal_volume     ?
_journal_issue      ?
_journal_page_first     ?
_journal_page_last     ?
_journal_paper_category     FO
_journal_paper_doi     ?
_journal_coeditor_code     ?

loop_
_publ_contact_author_name
_publ_contact_author_address
_publ_contact_author_email
'NAME'
;
ADDRESS
;
;
E-MAIL
;
_publ_contact_author_phone      ?

_publ_section_title
;
TITLE
;

loop_
_publ_author_name
_publ_author_address
'NAME'
;
ADDRESS
;

_publ_section_synopsis
;
;

data_I

_chemical_name_systematic
;
2-(5-Hydroxy-1H-indol-3-yl)ethanaminium 3-carboxypropanoate
;
_chemical_name_common     'Serotonin adipate'
_chemical_formula_moiety     'C10 H13 N2 O +, C6 H9 O4 -'
_chemical_formula_sum     'C16 H22 N2 O5'
_chemical_formula_iupac     'C10 H13 N2 O + , C6 H9 O4 -'
_chemical_formula_weight     322.36
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
    1 'x, y, z'
    2 '-x, -y, -z'

_cell_length_a     7.1582(3)
_cell_length_b     10.5984(7)
_cell_length_c     12.1715(7)
_cell_angle_alpha     113.202(6)
_cell_angle_beta     101.233(4)
_cell_angle_gamma     98.045(4)
_cell_volume     808.04(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2039
_cell_measurement_theta_min     1.8894
_cell_measurement_theta_max     26.3219
_cell_measurement_temperature     298
_cell_special_details     322.37
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.325
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     344
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2008)'
_exptl_absorpt_correction_T_min     0.99359
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature     298
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Gemini Ultra R'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.3457
_diffrn_reflns_number     10092
_diffrn_reflns_av_R_equivalents     0.0611
_diffrn_reflns_theta_min     1.89
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_theta_full     26.38
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger.
;
_reflns_number_total     3286
_reflns_number_gt     1849
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1080
_refine_ls_R_factor_gt     0.0514
_refine_ls_wR_factor_gt     0.0968
_refine_ls_wR_factor_ref     0.1205
_refine_ls_goodness_of_fit_ref     0.995
_refine_ls_restrained_S_all     0.995
_refine_ls_number_reflns     3286
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.160
_refine_diff_density_min     -0.197
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?

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'

_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_data_reduction      'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al.,
2008), PLATON (Spek, 2009) and CrystalExplorer (McKinnon
et al., 1998; Spackman & McKinnon, 2002)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009), enCIFer (Allen et al.,
2004) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.2468(4) -0.1305(3) 0.7987(2) 0.0523(6) Uani d . 1 1 . .
    N N2 0.2581(3) 0.0764(2) 0.4250(2) 0.0570(6) Uani d . 1 1 . .
    O O1 0.2346(2) 0.81214(18) 0.16669(15) 0.0549(5) Uani d . 1 1 . .
    O O2 0.3050(3) 0.65419(18) 0.00795(17) 0.0699(5) Uani d . 1 1 . .
    O O3 0.1196(2) 0.08911(16) 0.18057(15) 0.0518(4) Uani d . 1 1 . .
    O O4 0.3235(2) -0.01023(16) 0.07900(15) 0.0524(4) Uani d . 1 1 . .
    O O5 0.2448(3) 0.5954(2) 0.7695(2) 0.0704(6) Uani d . 1 1 . .
    C C1 0.2592(3) 0.6863(2) 0.1048(2) 0.0414(5) Uani d . 1 1 . .
    C C2 0.2307(4) 0.5868(2) 0.1627(2) 0.0445(6) Uani d . 1 1 . .
    C C3 0.2515(4) 0.4404(2) 0.0852(2) 0.0444(6) Uani d . 1 1 . .
    C C4 0.2290(4) 0.3395(2) 0.1442(2) 0.0464(6) Uani d . 1 1 . .
    C C5 0.2498(4) 0.1940(2) 0.0616(2) 0.0450(6) Uani d . 1 1 . .
    C C6 0.2288(3) 0.0849(2) 0.1118(2) 0.0392(5) Uani d . 1 1 . .
    C C7 0.2618(4) -0.1017(3) 0.6905(2) 0.0489(6) Uani d . 1 1 . .
    C C8 0.2533(4) 0.0492(3) 0.7188(2) 0.0481(6) Uani d . 1 1 . .
    C C9 0.2578(3) 0.0857(2) 0.6129(2) 0.0431(6) Uani d . 1 1 . .
    C C10 0.2552(3) 0.2220(2) 0.6173(2) 0.0429(6) Uani d . 1 1 . .
    C C11 0.2508(3) 0.3511(3) 0.7107(2) 0.0454(6) Uani d . 1 1 . .
    C C12 0.2476(3) 0.4643(3) 0.6829(2) 0.0523(6) Uani d . 1 1 . .
    C C13 0.2482(4) 0.4537(3) 0.5646(3) 0.0621(7) Uani d . 1 1 . .
    C C14 0.2534(4) 0.3290(3) 0.4724(3) 0.0614(7) Uani d . 1 1 . .
    C C15 0.2547(3) 0.2131(3) 0.4985(2) 0.0474(6) Uani d . 1 1 . .
    C C16 0.2572(3) 0.0000(3) 0.4943(2) 0.0526(6) Uani d . 1 1 . .
    H H1 0.261(3) 0.879(3) 0.124(2) 0.080(8) Uiso d . 1 1 . .
    H H1A 0.123(4) -0.117(3) 0.821(3) 0.094(10) Uiso d . 1 1 . .
    H H1B 0.249(3) -0.232(3) 0.775(2) 0.070(8) Uiso d . 1 1 . .
    H H1C 0.337(4) -0.072(3) 0.871(3) 0.099(11) Uiso d . 1 1 . .
    H H2 0.236(4) 0.040(3) 0.342(3) 0.101(11) Uiso d . 1 1 . .
    H H2A 0.325(3) 0.631(2) 0.245(2) 0.050(6) Uiso d . 1 1 . .
    H H2B 0.101(3) 0.584(2) 0.181(2) 0.071(8) Uiso d . 1 1 . .
    H H3A 0.156(3) 0.400(2) 0.003(2) 0.051(6) Uiso d . 1 1 . .
    H H3B 0.375(3) 0.448(2) 0.069(2) 0.060(7) Uiso d . 1 1 . .
    H H4A 0.101(3) 0.332(2) 0.162(2) 0.060(7) Uiso d . 1 1 . .
    H H4B 0.328(3) 0.380(2) 0.225(2) 0.070(8) Uiso d . 1 1 . .
    H H5 0.254(4) 0.598(3) 0.841(3) 0.088(11) Uiso d . 1 1 . .
    H H5A 0.143(3) 0.154(2) -0.021(2) 0.059(7) Uiso d . 1 1 . .
    H H5B 0.370(3) 0.204(2) 0.044(2) 0.067(8) Uiso d . 1 1 . .
    H H7A 0.145(3) -0.172(2) 0.618(2) 0.054(6) Uiso d . 1 1 . .
    H H7B 0.382(3) -0.123(2) 0.675(2) 0.056(7) Uiso d . 1 1 . .
    H H8A 0.129(3) 0.064(2) 0.748(2) 0.069(7) Uiso d . 1 1 . .
    H H8B 0.359(3) 0.112(2) 0.791(2) 0.056(7) Uiso d . 1 1 . .
    H H11 0.250(3) 0.360(2) 0.794(2) 0.051(6) Uiso d . 1 1 . .
    H H14 0.249(3) 0.321(2) 0.395(2) 0.062(7) Uiso d . 1 1 . .
    H H13 0.238(3) 0.540(3) 0.548(2) 0.067(7) Uiso d . 1 1 . .
    H H16 0.252(3) -0.104(3) 0.453(2) 0.069(8) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C7 . 1.483(3) ?
    N1 H1A . 0.99(3) ?
    N1 H1B . 1.00(3) ?
    N1 H1C . 0.90(3) ?
    N2 C16 . 1.381(3) ?
    N2 H2 . 0.89(3) ?
    O1 H1 . 1.04(3) ?
    O3 C6 . 1.245(2) ?
    O4 C6 . 1.271(2) ?
    O5 H5 . 0.84(3) ?
    O5 C12 . 1.380(3) ?
    C1 O1 . 1.305(3) ?
    C1 O2 . 1.217(3) ?
    C1 C2 . 1.493(3) ?
    C2 C3 . 1.511(3) ?
    C2 H2A . 0.98(2) ?
    C2 H2B . 1.00(2) ?
    C3 H3A . 0.98(2) ?
    C3 H3B . 0.94(2) ?
    C4 C3 . 1.512(3) ?
    C4 C5 . 1.520(3) ?
    C4 H4A . 0.98(2) ?
    C4 H4B . 0.99(2) ?
    C5 H5A . 1.02(2) ?
    C5 H5B . 0.93(2) ?
    C6 C5 . 1.508(3) ?
    C7 H7A . 1.02(2) ?
    C7 H7B . 0.95(2) ?
    C8 C7 . 1.510(3) ?
    C8 C9 . 1.490(3) ?
    C8 H8A . 1.03(2) ?
    C8 H8B . 0.96(2) ?
    C9 C16 . 1.368(3) ?
    C10 C9 . 1.427(3) ?
    C10 C11 . 1.402(3) ?
    C11 C12 . 1.371(3) ?
    C11 H11 . 0.99(2) ?
    C12 C13 . 1.400(3) ?
    C13 C14 . 1.367(4) ?
    C13 H13 . 1.02(2) ?
    C14 H14 . 0.91(2) ?
    C15 N2 . 1.377(3) ?
    C15 C10 . 1.411(3) ?
    C15 C14 . 1.385(3) ?
    C16 H16 . 1.00(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N1 C7 C8 . . 110.1(2) ?
    N1 C7 H7A . . 105.7(12) ?
    N1 C7 H7B . . 105.1(13) ?
    N2 C15 C10 . . 107.3(2) ?
    N2 C15 C14 . . 130.9(2) ?
    N2 C16 H16 . . 119.2(15) ?
    O1 C1 C2 . . 115.3(2) ?
    O2 C1 O1 . . 121.8(2) ?
    O2 C1 C2 . . 122.9(2) ?
    O3 C6 O4 . . 122.7(2) ?
    O3 C6 C5 . . 120.0(2) ?
    O4 C6 C5 . . 117.3(2) ?
    O5 C12 C13 . . 116.0(2) ?
    C1 O1 H1 . . 112.4(14) ?
    C1 C2 C3 . . 113.5(2) ?
    C1 C2 H2A . . 106.7(12) ?
    C1 C2 H2B . . 108.4(13) ?
    C2 C3 C4 . . 114.2(2) ?
    C2 C3 H3A . . 109.8(12) ?
    C2 C3 H3B . . 108.9(14) ?
    C3 C2 H2A . . 112.2(12) ?
    C3 C2 H2B . . 111.8(14) ?
    C3 C4 C5 . . 111.8(2) ?
    C3 C4 H4A . . 109.7(13) ?
    C3 C4 H4B . . 108.9(14) ?
    C4 C3 H3A . . 109.5(12) ?
    C4 C3 H3B . . 109.4(14) ?
    C4 C5 H5A . . 108.4(12) ?
    C4 C5 H5B . . 108.8(15) ?
    C5 C4 H4A . . 110.0(13) ?
    C5 C4 H4B . . 110.4(13) ?
    C6 C5 C4 . . 116.0(2) ?
    C6 C5 H5A . . 106.4(12) ?
    C6 C5 H5B . . 109.5(15) ?
    C7 N1 H1A . . 112.9(16) ?
    C7 N1 H1B . . 107.4(14) ?
    C7 N1 H1C . . 115(2) ?
    C7 C8 H8A . . 106.9(13) ?
    C7 C8 H8B . . 108.9(13) ?
    C8 C7 H7A . . 111.4(11) ?
    C8 C7 H7B . . 113.9(13) ?
    C9 C8 C7 . . 113.9(2) ?
    C9 C8 H8A . . 111.8(13) ?
    C9 C8 H8B . . 110.9(14) ?
    C9 C16 N2 . . 109.9(2) ?
    C9 C16 H16 . . 130.8(15) ?
    C10 C9 C8 . . 124.5(2) ?
    C10 C11 H11 . . 120.5(12) ?
    C11 C10 C15 . . 119.0(2) ?
    C11 C10 C9 . . 133.4(2) ?
    C11 C12 O5 . . 122.2(2) ?
    C11 C12 C13 . . 121.8(2) ?
    C12 O5 H5 . . 112(2) ?
    C12 C11 C10 . . 118.4(2) ?
    C12 C11 H11 . . 121.1(12) ?
    C12 C13 H13 . . 118.1(14) ?
    C13 C14 C15 . . 118.3(3) ?
    C13 C14 H14 . . 120.9(15) ?
    C14 C15 C10 . . 121.8(2) ?
    C14 C13 C12 . . 120.7(3) ?
    C14 C13 H13 . . 121.1(14) ?
    C15 N2 C16 . . 108.7(2) ?
    C15 N2 H2 . . 124(2) ?
    C15 C10 C9 . . 107.5(2) ?
    C15 C14 H14 . . 120.7(16) ?
    C16 N2 H2 . . 126(2) ?
    C16 C9 C10 . . 106.5(2) ?
    C16 C9 C8 . . 128.9(2) ?
    H1A N1 H1B . . 108(2) ?
    H1A N1 H1C . . 102(3) ?
    H1B N1 H1C . . 112(2) ?
    H2A C2 H2B . . 103.7(19) ?
    H3A C3 H3B . . 104.6(19) ?
    H4A C4 H4B . . 106(2) ?
    H5A C5 H5B . . 107(2) ?
    H7A C7 H7B . . 110.1(18) ?
    H8A C8 H8B . . 103.9(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O1 H1 O4 1_565 1.04(3) 1.53(3) 2.569(2) 172(2)
    N1 H1A O3 2_556 0.99(3) 1.80(3) 2.762(3) 163(2)
    N1 H1B O5 1_545 1.00(3) 1.80(3) 2.782(3) 166(2)
    O5 H5 O2 1_556 0.84(3) 1.82(3) 2.647(3) 164(3)

# start Validation Reply Form
_vrf_PUBL006_GLOBAL
;
PROBLEM: _publ_requested_journal is missing
RESPONSE: Example CIF
;
_vrf_PUBL012_GLOBAL
;
PROBLEM: _publ_section_abstract is missing.
RESPONSE: Example CIF
;
# end Validation Reply Form
