#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/38/4503827.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_4503827
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          '180-184 &#x00BA;C'
_chemical_name_common            '1:1 Co-crystal of 3HBA + BPEE'
_chemical_name_systematic
; 
 1:1 Co-crystal of 3-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                114.081(2)
_cell_angle_beta                 103.883(3)
_cell_angle_gamma                93.041(3)
_cell_formula_units_Z            2
_cell_length_a                   7.901(13)
_cell_length_b                   10.310(16)
_cell_length_c                   10.863(17)
_cell_measurement_temperature    100(2)
_cell_volume                     773(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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3945
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             336
_exptl_crystal_preparation       ethanol
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0416
_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)+(0.0560P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2326
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800565a_si_013.cif
_cod_data_source_block           ts460b
_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        772.8(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4503827
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
O1 O 0.98925(14) 1.04944(11) 1.26482(11) 0.0244(3) Uani 1 1 d .
H1O H 1.0629 1.1277 1.3598 0.029 Uiso 1 1 d R
O2 O 0.88221(14) 1.23740(10) 1.23848(11) 0.0237(3) Uani 1 1 d .
O3 O 0.46105(14) 1.00119(11) 0.74719(11) 0.0234(3) Uani 1 1 d .
H3O H 0.4037 0.9282 0.6576 0.028 Uiso 1 1 d R
C1 C 0.79317(19) 1.00265(15) 1.04491(15) 0.0175(3) Uani 1 1 d .
C2 C 0.67256(19) 1.04817(15) 0.96125(15) 0.0181(3) Uani 1 1 d .
H2 H 0.6530 1.1451 0.9981 0.022 Uiso 1 1 calc R
C3 C 0.58046(19) 0.95232(15) 0.82377(15) 0.0179(3) Uani 1 1 d .
C4 C 0.6104(2) 0.81067(16) 0.76963(16) 0.0200(3) Uani 1 1 d .
H4 H 0.5490 0.7450 0.6754 0.024 Uiso 1 1 calc R
C5 C 0.7306(2) 0.76570(16) 0.85402(16) 0.0213(4) Uani 1 1 d .
H5 H 0.7506 0.6689 0.8170 0.026 Uiso 1 1 calc R
C6 C 0.8218(2) 0.86040(15) 0.99148(16) 0.0202(3) Uani 1 1 d .
H6 H 0.9029 0.8286 1.0487 0.024 Uiso 1 1 calc R
C7 C 0.89084(19) 1.10899(15) 1.19171(16) 0.0193(3) Uani 1 1 d .
N11 N 0.18772(17) 0.22729(13) 0.52130(13) 0.0225(3) Uani 1 1 d .
C11 C 0.2560(2) 0.36379(16) 0.55732(16) 0.0251(4) Uani 1 1 d .
H11 H 0.2396 0.3965 0.4859 0.030 Uiso 1 1 calc R
C12 C 0.3490(2) 0.45931(16) 0.69331(16) 0.0249(4) Uani 1 1 d .
H12 H 0.3939 0.5555 0.7138 0.030 Uiso 1 1 calc R
C13 C 0.3771(2) 0.41431(16) 0.80074(16) 0.0198(3) Uani 1 1 d .
C14 C 0.3045(2) 0.27207(16) 0.76276(16) 0.0210(4) Uani 1 1 d .
H14 H 0.3185 0.2361 0.8317 0.025 Uiso 1 1 calc R
C15 C 0.2125(2) 0.18443(16) 0.62453(16) 0.0223(4) Uani 1 1 d .
H15 H 0.1638 0.0882 0.6010 0.027 Uiso 1 1 calc R
C16 C 0.4784(2) 0.51532(16) 0.94472(16) 0.0215(3) Uani 1 1 d .
H16 H 0.5167 0.6112 0.9607 0.026 Uiso 1 1 calc R
N21 N 0.28974(17) 0.80015(13) 0.47935(13) 0.0230(3) Uani 1 1 d .
C21 C 0.2942(2) 0.82532(17) 0.36792(17) 0.0249(4) Uani 1 1 d .
H21 H 0.3619 0.9130 0.3848 0.030 Uiso 1 1 calc R
C22 C 0.2061(2) 0.73122(16) 0.23061(16) 0.0229(4) Uani 1 1 d .
H22 H 0.2140 0.7545 0.1558 0.027 Uiso 1 1 calc R
C23 C 0.1054(2) 0.60161(16) 0.20208(16) 0.0194(3) Uani 1 1 d .
C24 C 0.1016(2) 0.57452(16) 0.31751(15) 0.0204(3) Uani 1 1 d .
H24 H 0.0361 0.4873 0.3036 0.024 Uiso 1 1 calc R
C25 C 0.1935(2) 0.67509(16) 0.45183(16) 0.0228(4) Uani 1 1 d .
H25 H 0.1883 0.6547 0.5287 0.027 Uiso 1 1 calc R
C26 C 0.0038(2) 0.49540(15) 0.06020(16) 0.0200(3) Uani 1 1 d .
H26 H -0.0631 0.4121 0.0533 0.024 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
C2 C1 C6 120.10(14) .
C2 C1 C7 118.76(13) .
C6 C1 C7 121.15(13) .
C1 C2 C3 120.25(13) .
O3 C3 C2 118.03(13) .
O3 C3 C4 122.22(13) .
C2 C3 C4 119.74(13) .
C5 C4 C3 119.71(14) .
C6 C5 C4 120.81(14) .
C5 C6 C1 119.38(13) .
O2 C7 O1 123.80(13) .
O2 C7 C1 123.28(13) .
O1 C7 C1 112.92(12) .
C11 N11 C15 117.03(13) .
N11 C11 C12 123.16(14) .
C11 C12 C13 119.91(14) .
C14 C13 C12 116.69(14) .
C14 C13 C16 123.50(13) .
C12 C13 C16 119.81(13) .
C15 C14 C13 119.50(14) .
N11 C15 C14 123.70(13) .
C16 C16 C13 125.93(18) 2_667
C25 N21 C21 116.65(13) .
N21 C21 C22 123.74(14) .
C21 C22 C23 119.60(14) .
C22 C23 C24 116.83(14) .
C22 C23 C26 123.97(14) .
C24 C23 C26 119.20(13) .
C25 C24 C23 119.76(14) .
N21 C25 C24 123.41(14) .
C26 C26 C23 126.29(17) 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.3282(17) .
O2 C7 1.2219(18) .
O3 C3 1.3608(18) .
C1 C2 1.391(2) .
C1 C6 1.394(2) .
C1 C7 1.494(2) .
C2 C3 1.391(2) .
C3 C4 1.392(2) .
C4 C5 1.390(2) .
C5 C6 1.386(2) .
N11 C11 1.3392(19) .
N11 C15 1.341(2) .
C11 C12 1.381(2) .
C12 C13 1.398(2) .
C13 C14 1.398(2) .
C13 C16 1.467(2) .
C14 C15 1.378(2) .
C16 C16 1.335(3) 2_667
N21 C25 1.3425(19) .
N21 C21 1.345(2) .
C21 C22 1.378(2) .
C22 C23 1.395(2) .
C23 C24 1.398(2) .
C23 C26 1.468(2) .
C24 C25 1.381(2) .
C26 C26 1.337(3) 2_565
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
O1 H1O N11 1.02 1.64 2.6482(16) 168.6 1_666
O3 H3O N21 0.93 1.80 2.7358(16) 174.8 .
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
C6 C1 C2 C3 -0.3(2) .
C7 C1 C2 C3 179.48(12) .
C1 C2 C3 O3 178.58(13) .
C1 C2 C3 C4 -0.5(2) .
O3 C3 C4 C5 -178.28(13) .
C2 C3 C4 C5 0.8(2) .
C3 C4 C5 C6 -0.2(2) .
C4 C5 C6 C1 -0.5(2) .
C2 C1 C6 C5 0.8(2) .
C7 C1 C6 C5 -178.96(13) .
C2 C1 C7 O2 -6.7(2) .
C6 C1 C7 O2 173.03(14) .
C2 C1 C7 O1 174.09(13) .
C6 C1 C7 O1 -6.15(19) .
C15 N11 C11 C12 0.2(2) .
N11 C11 C12 C13 0.6(3) .
C11 C12 C13 C14 -1.0(2) .
C11 C12 C13 C16 179.02(15) .
C12 C13 C14 C15 0.6(2) .
C16 C13 C14 C15 -179.45(15) .
C11 N11 C15 C14 -0.7(2) .
C13 C14 C15 N11 0.3(2) .
C14 C13 C16 C16 3.3(3) 2_667
C12 C13 C16 C16 -176.7(2) 2_667
C25 N21 C21 C22 0.3(2) .
N21 C21 C22 C23 0.0(2) .
C21 C22 C23 C24 -0.5(2) .
C21 C22 C23 C26 178.71(14) .
C22 C23 C24 C25 0.7(2) .
C26 C23 C24 C25 -178.54(13) .
C21 N21 C25 C24 -0.1(2) .
C23 C24 C25 N21 -0.5(2) .
C22 C23 C26 C26 1.9(3) 2_565
C24 C23 C26 C26 -178.90(19) 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144829
