#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/71/4507100.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4507100
loop_
_publ_author_name
'Tothadi, Srinu'
'Desiraju, Gautam R.'
_publ_section_title
;
 Synthon Modularity in 4-Hydroxybenzamide--Dicarboxylic Acid Cocrystals
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6188
_journal_paper_doi               10.1021/cg3013766
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_chemical_name_common            4-hydroxybenzamide
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9100(16)
_cell_length_b                   5.2740(11)
_cell_length_c                   8.4510(17)
_cell_measurement_reflns_used    1066
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     333.78(13)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_av_sigmaI/netI    0.1184
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3451
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1167P)²+0.0896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.1956
_reflns_number_gt                1428
_reflns_number_total             1504
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg3013766_si_003.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        333.78(12)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4507100
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
H9 H 0.563(5) 0.651(8) 0.025(5) 0.029(9) Uiso 1 1 d .
H2 H 0.876(5) 1.414(9) 0.761(5) 0.029(9) Uiso 1 1 d .
H1 H 0.959(7) 1.295(9) 0.905(6) 0.042(11) Uiso 1 1 d .
O2 O 0.6158(3) 0.8197(5) 0.0579(3) 0.0366(6) Uani 1 1 d .
O1 O 0.8644(3) 0.8576(4) 0.8497(2) 0.0259(5) Uani 1 1 d .
C1 C 0.6693(3) 0.8809(4) 0.2269(3) 0.0190(5) Uani 1 1 d .
C2 C 0.7772(3) 1.0016(4) 0.5698(3) 0.0151(5) Uani 1 1 d .
N1 N 0.8916(4) 1.2771(5) 0.8107(3) 0.0255(6) Uani 1 1 d .
C3 C 0.8470(3) 1.0430(5) 0.7541(3) 0.0178(5) Uani 1 1 d .
C4 C 0.8287(3) 1.1547(5) 0.4571(3) 0.0192(5) Uani 1 1 d .
H4 H 0.9006 1.3002 0.4970 0.023 Uiso 1 1 calc R
C5 C 0.6678(3) 0.7907(4) 0.5075(3) 0.0176(5) Uani 1 1 d .
H5 H 0.6312 0.6860 0.5819 0.021 Uiso 1 1 calc R
C6 C 0.7761(4) 1.0961(5) 0.2889(3) 0.0212(6) Uani 1 1 d .
H6 H 0.8121 1.2015 0.2144 0.025 Uiso 1 1 calc R
C7 C 0.6126(3) 0.7334(5) 0.3382(3) 0.0193(5) Uani 1 1 d .
H7 H 0.5357 0.5930 0.2975 0.023 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0420(14) 0.0401(13) 0.0255(11) -0.0022(9) 0.0078(10) -0.0039(11)
O1 0.0349(12) 0.0240(9) 0.0169(8) 0.0034(7) 0.0057(8) -0.0005(8)
C1 0.0182(12) 0.0208(12) 0.0158(11) 0.0011(9) 0.0026(10) 0.0015(9)
C2 0.0147(11) 0.0161(11) 0.0137(10) 0.0004(8) 0.0032(9) 0.0033(8)
N1 0.0349(14) 0.0215(11) 0.0161(10) -0.0019(9) 0.0025(10) -0.0027(9)
C3 0.0146(11) 0.0226(12) 0.0145(11) -0.0003(9) 0.0026(9) 0.0005(9)
C4 0.0210(12) 0.0165(10) 0.0197(11) 0.0019(9) 0.0059(9) -0.0017(9)
C5 0.0181(11) 0.0195(12) 0.0148(10) 0.0015(8) 0.0049(9) 0.0008(9)
C6 0.0241(13) 0.0223(12) 0.0186(12) 0.0041(9) 0.0089(11) -0.0026(9)
C7 0.0175(12) 0.0211(11) 0.0177(11) -0.0020(9) 0.0034(10) -0.0023(8)
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
C1 O2 H9 118(2)
O2 C1 C7 120.2(2)
O2 C1 C6 121.1(2)
C7 C1 C6 118.7(2)
C5 C2 C4 118.6(2)
C5 C2 C3 119.0(2)
C4 C2 C3 122.2(2)
C3 N1 H2 131(3)
C3 N1 H1 118(3)
H2 N1 H1 110(4)
O1 C3 N1 122.2(2)
O1 C3 C2 119.2(2)
N1 C3 C2 118.5(2)
C6 C4 C2 120.8(2)
C6 C4 H4 119.6
C2 C4 H4 119.6
C7 C5 C2 120.7(2)
C7 C5 H5 119.6
C2 C5 H5 119.6
C4 C6 C1 120.5(2)
C4 C6 H6 119.7
C1 C6 H6 119.7
C5 C7 C1 120.6(2)
C5 C7 H7 119.7
C1 C7 H7 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.391(3)
O2 H9 0.99(4)
O1 C3 1.248(3)
C1 C7 1.401(3)
C1 C6 1.411(3)
C2 C5 1.403(3)
C2 C4 1.406(3)
C2 C3 1.491(3)
N1 C3 1.330(3)
N1 H2 0.83(5)
N1 H1 0.81(5)
C4 C6 1.381(3)
C4 H4 0.9500
C5 C7 1.387(3)
C5 H5 0.9500
C6 H6 0.9500
C7 H7 0.9500
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
C5 C2 C3 O1 25.6(3)
C4 C2 C3 O1 -149.1(2)
C5 C2 C3 N1 -155.5(2)
C4 C2 C3 N1 29.8(4)
C5 C2 C4 C6 -1.3(4)
C3 C2 C4 C6 173.4(2)
C4 C2 C5 C7 0.4(4)
C3 C2 C5 C7 -174.5(2)
C2 C4 C6 C1 0.0(4)
O2 C1 C6 C4 -179.9(2)
C7 C1 C6 C4 2.3(4)
C2 C5 C7 C1 1.9(4)
O2 C1 C7 C5 178.9(2)
C6 C1 C7 C5 -3.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 58563
2 PubChem 65052
