#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/70/4507090.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_4507090
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            'C9 H10 N O4'
_chemical_formula_weight         196.10
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 113.321(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.886(5)
_cell_length_b                   5.118(3)
_cell_length_c                   21.046(10)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     878.9(8)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8846
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7568
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0420
_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)+(0.0624P)²+0.3087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                1896
_reflns_number_total             2015
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg3013766_si_003.cif
_cod_data_source_block           02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_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_sg_symbol_H-M      'P 21/c'
_cod_database_code               4507090
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'
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
H5 H -0.240(2) 0.602(3) 0.2556(10) 0.025(4) Uiso 1 1 d
H10 H 0.4653(19) 0.772(3) 0.0130(8) 0.015(4) Uiso 1 1 d
H3 H -0.480(3) 0.398(5) 0.2453(13) 0.046(6) Uiso 1 1 d
H7 H -0.235(2) -0.038(3) 0.0928(9) 0.021(4) Uiso 1 1 d
H6 H -0.437(2) -0.057(4) 0.1436(10) 0.032(5) Uiso 1 1 d
H4 H -0.040(2) 0.620(4) 0.2061(10) 0.027(4) Uiso 1 1 d
H9 H 0.585(2) 0.582(3) 0.0723(9) 0.021(4) Uiso 1 1 d
H2 H 0.007(2) -0.038(4) 0.0876(10) 0.033(5) Uiso 1 1 d
H1 H 0.115(2) 0.145(4) 0.0671(11) 0.036(5) Uiso 1 1 d
H8 H 0.231(3) 0.588(4) 0.0992(12) 0.048(6) Uiso 1 1 d
O2 O 0.26483(12) 0.2959(2) 0.01885(6) 0.0273(3) Uani 1 1 d
O1 O 0.32280(12) 0.6407(2) 0.09004(6) 0.0265(3) Uani 1 1 d
C1 C 0.48713(14) 0.5823(2) 0.02738(6) 0.0169(3) Uani 1 1 d
C2 C 0.34634(15) 0.4884(2) 0.04420(7) 0.0173(3) Uani 1 1 d
O3 O 0.07218(12) 0.54120(19) 0.11772(6) 0.0246(3) Uani 1 1 d
O4 O -0.47259(12) 0.25089(19) 0.22782(6) 0.0234(3) Uani 1 1 d
N1 N 0.03989(16) 0.1204(2) 0.08384(7) 0.0260(3) Uani 1 1 d
C4 C -0.12008(14) 0.2957(2) 0.14467(6) 0.0152(3) Uani 1 1 d
C7 C -0.35366(15) 0.2706(2) 0.20187(7) 0.0168(3) Uani 1 1 d
C5 C -0.23536(15) 0.0937(2) 0.12625(7) 0.0171(3) Uani 1 1 d
C6 C -0.35293(15) 0.0825(2) 0.15439(7) 0.0185(3) Uani 1 1 d
C8 C -0.23793(15) 0.4705(2) 0.22177(7) 0.0173(3) Uani 1 1 d
C3 C 0.00441(15) 0.3250(2) 0.11408(7) 0.0170(3) Uani 1 1 d
C9 C -0.12271(15) 0.4825(2) 0.19248(7) 0.0162(3) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 H8 112.3(14) . .
C2 C1 C1 112.99(13) . 3_665
C2 C1 H10 107.3(9) . .
C1 C1 H10 112.0(9) 3_665 .
C2 C1 H9 105.6(10) . .
C1 C1 H9 112.4(10) 3_665 .
H10 C1 H9 106.1(13) . .
O2 C2 O1 124.12(12) . .
O2 C2 C1 124.16(12) . .
O1 C2 C1 111.71(11) . .
C7 O4 H3 108.1(16) . .
C3 N1 H2 122.4(13) . .
C3 N1 H1 116.3(13) . .
H2 N1 H1 120.2(18) . .
C9 C4 C5 119.16(12) . .
C9 C4 C3 118.01(11) . .
C5 C4 C3 122.82(11) . .
O4 C7 C6 117.33(11) . .
O4 C7 C8 121.87(12) . .
C6 C7 C8 120.81(12) . .
C6 C5 C4 120.24(12) . .
C6 C5 H7 119.6(10) . .
C4 C5 H7 120.1(10) . .
C7 C6 C5 119.73(11) . .
C7 C6 H6 116.5(12) . .
C5 C6 H6 123.7(12) . .
C9 C8 C7 119.03(12) . .
C9 C8 H5 121.2(11) . .
C7 C8 H5 119.8(11) . .
O3 C3 N1 121.94(12) . .
O3 C3 C4 119.02(11) . .
N1 C3 C4 119.04(11) . .
C8 C9 C4 121.01(11) . .
C8 C9 H4 120.1(11) . .
C4 C9 H4 118.8(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C2 1.2143(17) .
O1 C2 1.3198(17) .
O1 H8 0.94(2) .
C1 C2 1.5073(18) .
C1 C1 1.516(2) 3_665
C1 H10 1.012(16) .
C1 H9 1.000(16) .
O3 C3 1.2476(17) .
O4 C7 1.3719(16) .
O4 H3 0.85(2) .
N1 C3 1.3267(18) .
N1 H2 0.87(2) .
N1 H1 0.88(2) .
C4 C9 1.3949(18) .
C4 C5 1.3980(18) .
C4 C3 1.4914(18) .
C7 C6 1.3893(18) .
C7 C8 1.3923(18) .
C5 C6 1.3911(18) .
C5 H7 0.977(18) .
C6 H6 0.994(19) .
C8 C9 1.3898(19) .
C8 H5 0.987(19) .
C9 H4 0.972(18) .
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
C1 C1 C2 O2 2.6(2) 3_665
C1 C1 C2 O1 -177.63(13) 3_665
C9 C4 C5 C6 1.20(18) .
C3 C4 C5 C6 -177.31(11) .
O4 C7 C6 C5 179.79(11) .
C8 C7 C6 C5 -0.05(19) .
C4 C5 C6 C7 -1.13(19) .
O4 C7 C8 C9 -178.69(11) .
C6 C7 C8 C9 1.14(19) .
C9 C4 C3 O3 -17.95(17) .
C5 C4 C3 O3 160.57(12) .
C9 C4 C3 N1 162.02(12) .
C5 C4 C3 N1 -19.47(18) .
C7 C8 C9 C4 -1.07(19) .
C5 C4 C9 C8 -0.09(18) .
C3 C4 C9 C8 178.49(11) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146309
