#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:42:09 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/22/2242201.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242201
loop_
_publ_author_name
'Chesna, Aaron M.'
'Cox, Jordan M.'
'Basso, Sanjukta'
'Benedict, Jason B.'
_publ_section_title
;
 Hydrogen-bonded co-crystal structure of benzoic acid and zwitterionic
 <small>L</small>-proline
;
_journal_coeditor_code           LH5828
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              369
_journal_page_last               371
_journal_paper_doi               10.1107/S2056989017001785
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C5 H9 N O2, C7 H6 O2'
_chemical_formula_moiety         'C5 H9 N O2, C7 H6 O2'
_chemical_formula_sum            'C12 H15 N O4'
_chemical_formula_weight         237.25
_chemical_name_common
;
Benzoic acid--L-proline (1/1)
;
_chemical_name_systematic
;
Benzoic acid--pyrrolidin-1-ium-2-carboxylate (1/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6993(7)
_cell_length_b                   12.0762(13)
_cell_length_c                   16.6839(19)
_cell_measurement_reflns_used    2011
_cell_measurement_temperature    90
_cell_measurement_theta_max      24.654
_cell_measurement_theta_min      3.374
_cell_volume                     1148.3(2)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13711
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.425
_diffrn_reflns_theta_min         2.082
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details
;
Flack x determined using 824 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0344P)²+0.0827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2375
_reflns_number_total             2880
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5828sup1.cif
_cod_data_source_block           I
_cod_database_code               2242201
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_occupancy
O O1 0.6846(3) 0.69609(14) 0.45367(10) 0.0186(4) Uani d 1
O O2 0.8438(3) 0.62955(13) 0.34146(9) 0.0131(4) Uani d 1
N N1 0.2560(3) 0.72586(15) 0.39137(11) 0.0118(4) Uani d 1
H H1A 0.1317 0.6787 0.3892 0.014 Uiso calc 1
H H1B 0.3091 0.7281 0.4428 0.014 Uiso calc 1
C C1 0.1825(5) 0.8393(2) 0.36504(13) 0.0161(5) Uani d 1
H H1C 0.2726 0.8972 0.3936 0.019 Uiso calc 1
H H1D 0.0129 0.8512 0.3745 0.019 Uiso calc 1
C C2 0.2381(4) 0.8397(2) 0.27615(13) 0.0161(5) Uani d 1
H H2A 0.2546 0.9162 0.2556 0.019 Uiso calc 1
H H2B 0.1152 0.8008 0.2451 0.019 Uiso calc 1
C C3 0.4714(4) 0.7775(2) 0.27268(14) 0.0149(5) Uani d 1
H H3A 0.6039 0.8275 0.2854 0.018 Uiso calc 1
H H3B 0.4968 0.7451 0.2189 0.018 Uiso calc 1
C C4 0.4481(4) 0.68629(19) 0.33630(13) 0.0110(5) Uani d 1
H H4 0.3995 0.6154 0.3101 0.013 Uiso calc 1
C C5 0.6756(4) 0.66858(18) 0.38222(14) 0.0119(5) Uani d 1
O O3 0.2945(3) 0.46855(14) 0.70526(9) 0.0174(4) Uani d 1
O O4 0.6289(3) 0.37449(14) 0.68623(9) 0.0173(4) Uani d 1
H H4A 0.6367 0.3789 0.7364 0.026 Uiso calc 1
C C6 0.3977(4) 0.41409(19) 0.57268(14) 0.0125(5) Uani d 1
C C7 0.1924(5) 0.4564(2) 0.54035(14) 0.0183(5) Uani d 1
H H7 0.0767 0.4870 0.5749 0.022 Uiso calc 1
C C8 0.1538(5) 0.4548(2) 0.45852(14) 0.0201(6) Uani d 1
H H8 0.0124 0.4839 0.4369 0.024 Uiso calc 1
C C9 0.3232(5) 0.41022(19) 0.40809(14) 0.0196(6) Uani d 1
H H9 0.2987 0.4095 0.3518 0.024 Uiso calc 1
C C10 0.5282(5) 0.3668(2) 0.44000(15) 0.0200(6) Uani d 1
H H10 0.6438 0.3363 0.4054 0.024 Uiso calc 1
C C11 0.5651(5) 0.3678(2) 0.52216(14) 0.0162(5) Uani d 1
H H11 0.7046 0.3369 0.5439 0.019 Uiso calc 1
C C12 0.4324(4) 0.42155(19) 0.66114(14) 0.0132(5) Uani d 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1A N1 H1B 108.4
C1 N1 H1A 110.0
C1 N1 H1B 110.0
C1 N1 C4 108.32(18)
C4 N1 H1A 110.0
C4 N1 H1B 110.0
N1 C1 H1C 111.1
N1 C1 H1D 111.1
N1 C1 C2 103.39(18)
H1C C1 H1D 109.0
C2 C1 H1C 111.1
C2 C1 H1D 111.1
C1 C2 H2A 111.3
C1 C2 H2B 111.3
C1 C2 C3 102.53(19)
H2A C2 H2B 109.2
C3 C2 H2A 111.3
C3 C2 H2B 111.3
C2 C3 H3A 110.8
C2 C3 H3B 110.8
C2 C3 C4 104.55(19)
H3A C3 H3B 108.9
C4 C3 H3A 110.8
C4 C3 H3B 110.8
N1 C4 C3 104.87(18)
N1 C4 H4 109.6
N1 C4 C5 110.90(18)
C3 C4 H4 109.6
C5 C4 C3 112.05(19)
C5 C4 H4 109.6
O1 C5 O2 125.8(2)
O1 C5 C4 118.9(2)
O2 C5 C4 115.28(19)
C12 O4 H4A 109.5
C7 C6 C11 119.5(2)
C7 C6 C12 118.3(2)
C11 C6 C12 122.2(2)
C6 C7 H7 119.6
C8 C7 C6 120.8(2)
C8 C7 H7 119.6
C7 C8 H8 120.2
C7 C8 C9 119.6(3)
C9 C8 H8 120.2
C8 C9 H9 120.0
C10 C9 C8 120.0(2)
C10 C9 H9 120.0
C9 C10 H10 119.9
C9 C10 C11 120.3(2)
C11 C10 H10 119.9
C6 C11 H11 120.1
C10 C11 C6 119.9(2)
C10 C11 H11 120.1
O3 C12 O4 123.7(2)
O3 C12 C6 122.7(2)
O4 C12 C6 113.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.239(3)
O2 C5 1.266(3)
N1 H1A 0.9100
N1 H1B 0.9100
N1 C1 1.498(3)
N1 C4 1.507(3)
C1 H1C 0.9900
C1 H1D 0.9900
C1 C2 1.517(3)
C2 H2A 0.9900
C2 H2B 0.9900
C2 C3 1.528(3)
C3 H3A 0.9900
C3 H3B 0.9900
C3 C4 1.536(3)
C4 H4 1.0000
C4 C5 1.521(3)
O3 C12 1.217(3)
O4 H4A 0.8400
O4 C12 1.324(3)
C6 C7 1.386(3)
C6 C11 1.391(3)
C6 C12 1.492(3)
C7 H7 0.9500
C7 C8 1.383(3)
C8 H8 0.9500
C8 C9 1.389(4)
C9 H9 0.9500
C9 C10 1.386(4)
C10 H10 0.9500
C10 C11 1.387(3)
C11 H11 0.9500
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
N1 H1A O2 1_455 0.91 1.92 2.751(3) 151.3
N1 H1B O1 . 0.91 2.18 2.679(3) 113.5
N1 H1B O1 3_466 0.91 2.08 2.782(2) 133.0
C4 H4 O3 2_564 1.00 2.30 3.192(3) 147.3
O4 H4A O2 2_665 0.84 1.76 2.595(2) 173.1
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
N1 C1 C2 C3 -39.6(2)
N1 C4 C5 O1 -6.0(3)
N1 C4 C5 O2 176.36(18)
C1 N1 C4 C3 -4.2(2)
C1 N1 C4 C5 117.0(2)
C1 C2 C3 C4 37.3(2)
C2 C3 C4 N1 -20.6(2)
C2 C3 C4 C5 -141.01(19)
C3 C4 C5 O1 110.8(2)
C3 C4 C5 O2 -66.8(3)
C4 N1 C1 C2 27.4(2)
C6 C7 C8 C9 -0.1(4)
C7 C6 C11 C10 1.6(4)
C7 C6 C12 O3 -4.2(3)
C7 C6 C12 O4 177.2(2)
C7 C8 C9 C10 0.7(4)
C8 C9 C10 C11 -0.1(4)
C9 C10 C11 C6 -1.0(4)
C11 C6 C7 C8 -1.0(4)
C11 C6 C12 O3 174.9(2)
C11 C6 C12 O4 -3.7(3)
C12 C6 C7 C8 178.1(2)
C12 C6 C11 C10 -177.5(2)

_cod_database_fobs_code 2242201
