#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/38/4503826.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_4503826
loop_
_publ_author_name
'Shattock, Tanise R.'
'Arora, Kapildev K.'
'Vishweshwar, Peddy'
'Zaworotko, Michael J.'
_publ_section_title
;
 Hierarchy of Supramolecular Synthons: Persistent Carboxylic
 Acid···Pyridine Hydrogen Bonds in Cocrystals That
 also Contain a Hydroxyl Moiety
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4533
_journal_paper_doi               10.1021/cg800565a
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C12 H10 N2, C7 H6 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_chemical_melting_point          '184-186 &#x00BA;C'
_chemical_name_common            '1:1 Co-crystal of 4HBA + BPEE'
_chemical_name_systematic
; 
 1:1 Co-crystal of 4-hydroxybenzoic acid and BPEE 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.046(6)
_cell_angle_beta                 94.058(7)
_cell_angle_gamma                103.928(6)
_cell_formula_units_Z            2
_cell_length_a                   6.193(19)
_cell_length_b                   6.957(2)
_cell_length_c                   18.499(5)
_cell_measurement_temperature    100(2)
_cell_volume                     767(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.1127
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3082
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             336
_exptl_crystal_preparation       methanol
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0682
_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)+(0.0499P)²+0.2338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                1448
_reflns_number_total             2508
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800565a_si_012.cif
_cod_data_source_block           ts461a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        767.1(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4503826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O17 O -0.0554(5) 0.2909(4) 0.35690(14) 0.0297(8) Uani 1 1 d .
O18 O 0.2692(4) 0.3131(4) 0.30759(14) 0.0263(7) Uani 1 1 d .
H18 H 0.2919 0.2026 0.3434 0.039 Uiso 1 1 d R
O19 O -0.0316(4) 1.0065(4) 0.16202(14) 0.0264(7) Uani 1 1 d .
H19 H 0.0839 1.0470 0.1277 0.040 Uiso 1 1 d R
C11 C 0.0041(6) 0.8554(6) 0.1988(2) 0.0210(10) Uani 1 1 d .
C12 C -0.1667(6) 0.7602(6) 0.2385(2) 0.0248(10) Uani 1 1 d .
H12 H -0.3003 0.8041 0.2401 0.030 Uiso 1 1 calc R
C13 C -0.1401(6) 0.6016(6) 0.2756(2) 0.0233(10) Uani 1 1 d .
H13 H -0.2570 0.5378 0.3025 0.028 Uiso 1 1 calc R
C14 C 0.0533(6) 0.5333(6) 0.27451(19) 0.0189(9) Uani 1 1 d .
C15 C 0.2218(6) 0.6294(6) 0.23415(19) 0.0191(9) Uani 1 1 d .
H15 H 0.3546 0.5843 0.2321 0.023 Uiso 1 1 calc R
C16 C 0.1990(6) 0.7896(6) 0.1970(2) 0.0213(10) Uani 1 1 d .
H16 H 0.3163 0.8541 0.1705 0.026 Uiso 1 1 calc R
C17 C 0.0823(7) 0.3674(6) 0.3160(2) 0.0234(10) Uani 1 1 d .
N21 N 0.3151(5) 1.0173(5) 0.38041(16) 0.0235(8) Uani 1 1 d .
C21 C 0.4981(7) 0.9482(6) 0.3751(2) 0.0251(10) Uani 1 1 d .
H21 H 0.6048 1.0066 0.3438 0.030 Uiso 1 1 calc R
C22 C 0.5386(7) 0.7964(6) 0.4129(2) 0.0269(10) Uani 1 1 d .
H22 H 0.6695 0.7507 0.4065 0.032 Uiso 1 1 calc R
C23 C 0.3873(6) 0.7094(6) 0.4606(2) 0.0201(9) Uani 1 1 d .
C24 C 0.1987(6) 0.7827(6) 0.4659(2) 0.0241(10) Uani 1 1 d .
H24 H 0.0905 0.7296 0.4975 0.029 Uiso 1 1 calc R
C25 C 0.1680(7) 0.9338(6) 0.4249(2) 0.0256(10) Uani 1 1 d .
H25 H 0.0363 0.9797 0.4287 0.031 Uiso 1 1 calc R
C26 C 0.4233(6) 0.5517(6) 0.5048(2) 0.0214(10) Uani 1 1 d .
H26 H 0.3303 0.5214 0.5431 0.026 Uiso 1 1 calc R
N31 N 0.3291(5) 0.1662(5) 0.08816(18) 0.0243(9) Uani 1 1 d .
C31 C 0.5257(7) 0.2514(6) 0.1269(2) 0.0266(10) Uani 1 1 d .
H31 H 0.5339 0.2490 0.1783 0.032 Uiso 1 1 calc R
C32 C 0.7159(7) 0.3420(6) 0.0968(2) 0.0242(10) Uani 1 1 d .
H32 H 0.8506 0.3991 0.1271 0.029 Uiso 1 1 calc R
C33 C 0.7100(6) 0.3494(5) 0.0211(2) 0.0191(10) Uani 1 1 d .
C34 C 0.5059(6) 0.2582(6) -0.0193(2) 0.0207(9) Uani 1 1 d .
H34 H 0.4924 0.2573 -0.0709 0.025 Uiso 1 1 calc R
C35 C 0.3245(7) 0.1697(6) 0.0156(2) 0.0249(10) Uani 1 1 d .
H35 H 0.1884 0.1076 -0.0133 0.030 Uiso 1 1 calc R
C36 C 0.8994(6) 0.4508(6) -0.0155(2) 0.0228(10) Uani 1 1 d .
H36 H 0.8765 0.4460 -0.0671 0.027 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
O19 C11 C16 122.9(4) .
O19 C11 C12 117.6(4) .
C16 C11 C12 119.5(4) .
C13 C12 C11 119.7(4) .
C12 C13 C14 121.7(4) .
C13 C14 C15 117.8(4) .
C13 C14 C17 121.2(4) .
C15 C14 C17 121.0(4) .
C16 C15 C14 121.4(4) .
C15 C16 C11 119.9(4) .
O17 C17 O18 123.0(4) .
O17 C17 C14 122.4(4) .
O18 C17 C14 114.6(4) .
C25 N21 C21 117.5(4) .
N21 C21 C22 123.0(4) .
C21 C22 C23 120.2(4) .
C24 C23 C22 116.3(4) .
C24 C23 C26 120.4(4) .
C22 C23 C26 123.3(4) .
C23 C24 C25 120.0(4) .
N21 C25 C24 123.0(4) .
C26 C26 C23 124.9(5) 2_666
C31 N31 C35 116.3(4) .
N31 C31 C32 124.1(4) .
C31 C32 C33 119.6(4) .
C34 C33 C32 116.3(4) .
C34 C33 C36 119.9(3) .
C32 C33 C36 123.8(3) .
C35 C34 C33 119.9(4) .
N31 C35 C34 123.7(4) .
C36 C36 C33 126.9(5) 2_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O17 C17 1.236(4) .
O18 C17 1.316(5) .
O19 C11 1.353(5) .
C11 C16 1.391(5) .
C11 C12 1.399(5) .
C12 C13 1.386(6) .
C13 C14 1.392(5) .
C14 C15 1.399(5) .
C14 C17 1.479(5) .
C15 C16 1.389(5) .
N21 C25 1.334(5) .
N21 C21 1.339(5) .
C21 C22 1.379(6) .
C22 C23 1.401(5) .
C23 C24 1.389(5) .
C23 C26 1.474(6) .
C24 C25 1.390(5) .
C26 C26 1.336(8) 2_666
N31 C31 1.342(5) .
N31 C35 1.343(5) .
C31 C32 1.375(5) .
C32 C33 1.404(5) .
C33 C34 1.399(5) .
C33 C36 1.460(5) .
C34 C35 1.378(5) .
C36 C36 1.331(7) 2_765
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O18 H18 N21 1.08 1.54 2.617(4) 168.8 1_545
O19 H19 N31 1.00 1.79 2.756(4) 163.8 1_565
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_4
O19 C11 C12 C13 178.5(3) .
C16 C11 C12 C13 -0.1(5) .
C11 C12 C13 C14 0.0(6) .
C12 C13 C14 C15 -0.4(5) .
C12 C13 C14 C17 178.3(3) .
C13 C14 C15 C16 0.8(5) .
C17 C14 C15 C16 -177.8(3) .
C14 C15 C16 C11 -0.9(5) .
O19 C11 C16 C15 -177.9(3) .
C12 C11 C16 C15 0.5(5) .
C13 C14 C17 O17 -4.7(6) .
C15 C14 C17 O17 173.8(3) .
C13 C14 C17 O18 177.3(3) .
C15 C14 C17 O18 -4.1(5) .
C25 N21 C21 C22 0.3(6) .
N21 C21 C22 C23 -1.3(6) .
C21 C22 C23 C24 1.0(5) .
C21 C22 C23 C26 -177.7(3) .
C22 C23 C24 C25 0.2(5) .
C26 C23 C24 C25 178.9(3) .
C21 N21 C25 C24 0.9(5) .
C23 C24 C25 N21 -1.2(6) .
C24 C23 C26 C26 168.1(5) 2_666
C22 C23 C26 C26 -13.3(7) 2_666
C35 N31 C31 C32 1.0(6) .
N31 C31 C32 C33 0.3(6) .
C31 C32 C33 C34 -1.2(6) .
C31 C32 C33 C36 176.7(4) .
C32 C33 C34 C35 0.7(6) .
C36 C33 C34 C35 -177.3(4) .
C31 N31 C35 C34 -1.5(6) .
C33 C34 C35 N31 0.7(6) .
C34 C33 C36 C36 177.7(5) 2_765
C32 C33 C36 C36 -0.1(8) 2_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144828
