#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508138.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_4508138
loop_
_publ_author_name
'Lemmerer, Andreas'
'Adsmond, Daniel A.'
'Esterhuysen, Catharine'
'Bernstein, Joel'
_publ_section_title
;
 Polymorphic Co-crystals from Polymorphic Co-crystal Formers: Competition
 between Carboxylic Acid...Pyridine and Phenol...Pyridine Hydrogen Bonds
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3935
_journal_paper_doi               10.1021/cg4006357
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C7 H6 O4, C6 H6 N2 O1'
_chemical_formula_sum            'C13 H12 N2 O5'
_chemical_formula_weight         276.25
_chemical_name_systematic
;
 (2,4-dihydroxybenzoic acid).(nicotinamide) Form I
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-03-03T18:17:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                96.617(5)
_cell_angle_beta                 91.353(4)
_cell_angle_gamma                94.753(7)
_cell_formula_units_Z            2
_cell_length_a                   5.8411(9)
_cell_length_b                   8.1695(14)
_cell_length_c                   13.4181(19)
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      2.52
_cell_volume                     633.49(17)
_computing_cell_refinement       'Bruker SAINT+, Bruker (1999)'
_computing_data_collection       'Bruker SMART, Bruker (1998)'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5949
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         1.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.0330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1555
_reflns_number_total             2338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4006357_si_002.cif
_cod_data_source_block           4(I)
_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 2.4.2 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-1
_cod_database_code               4508138
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
C1 C 0.3725(3) 0.4297(2) 0.23386(14) 0.0380(4) Uani 1 1 d .
C2 C 0.1646(3) 0.3293(2) 0.21337(14) 0.0405(5) Uani 1 1 d .
C3 C 0.1272(3) 0.2292(2) 0.12345(14) 0.0463(5) Uani 1 1 d .
H3A H -0.011 0.1641 0.1105 0.056 Uiso 1 1 calc R
C4 C 0.2959(3) 0.2256(2) 0.05241(14) 0.0450(5) Uani 1 1 d .
C5 C 0.5023(3) 0.3245(2) 0.07214(15) 0.0503(5) Uani 1 1 d .
H5 H 0.6157 0.3224 0.0246 0.06 Uiso 1 1 calc R
C6 C 0.5384(3) 0.4243(2) 0.16078(15) 0.0466(5) Uani 1 1 d .
H6 H 0.6763 0.49 0.1727 0.056 Uiso 1 1 calc R
C7 C 0.4098(3) 0.5343(2) 0.32939(14) 0.0420(5) Uani 1 1 d .
O1 O 0.6093(2) 0.62287(17) 0.34150(10) 0.0561(4) Uani 1 1 d .
H1 H 0.6125 0.6837 0.3947 0.084 Uiso 1 1 calc R
O2 O 0.2651(2) 0.53975(17) 0.39524(10) 0.0550(4) Uani 1 1 d .
O3 O 0.2528(3) 0.1242(2) -0.03300(11) 0.0676(5) Uani 1 1 d .
H3 H 0.3597 0.136 -0.0708 0.081 Uiso 1 1 calc R
O4 O -0.0023(2) 0.32635(19) 0.28172(11) 0.0589(4) Uani 1 1 d .
H4 H 0.0359 0.3935 0.3307 0.071 Uiso 1 1 calc R
C8 C 0.6383(3) 0.9729(2) 0.66199(13) 0.0380(4) Uani 1 1 d .
C9 C 0.5099(3) 1.0026(2) 0.74669(14) 0.0438(5) Uani 1 1 d .
H9 H 0.3658 0.9453 0.7479 0.053 Uiso 1 1 calc R
C10 C 0.7902(4) 1.1876(3) 0.82410(15) 0.0520(5) Uani 1 1 d .
H10 H 0.8437 1.2603 0.8798 0.062 Uiso 1 1 calc R
C11 C 0.9308(4) 1.1668(3) 0.74342(16) 0.0536(6) Uani 1 1 d .
H11 H 1.0751 1.2246 0.7446 0.064 Uiso 1 1 calc R
C12 C 0.8528(3) 1.0588(2) 0.66116(15) 0.0466(5) Uani 1 1 d .
H12 H 0.9434 1.0435 0.6053 0.056 Uiso 1 1 calc R
C13 C 0.5574(3) 0.8524(2) 0.57340(14) 0.0404(5) Uani 1 1 d .
N1 N 0.3534(3) 0.7684(2) 0.57569(12) 0.0542(5) Uani 1 1 d .
H1S H 0.3039 0.6987 0.5253 0.081 Uiso 1 1 calc R
H1A H 0.2707 0.7836 0.6276 0.081 Uiso 1 1 calc R
N2 N 0.5811(3) 1.1087(2) 0.82656(12) 0.0483(4) Uani 1 1 d .
O5 O 0.6804(2) 0.83351(17) 0.50009(10) 0.0552(4) 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.07
0 0 -1 0.07
-2 4 -1 0.26
2 -4 1 0.26
-2 0 -1 0.32
3 1 2 0.32
2 -1 1 0.28
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 118.06(16)
C6 C1 C7 121.85(17)
C2 C1 C7 120.09(17)
O4 C2 C3 118.09(17)
O4 C2 C1 121.15(16)
C3 C2 C1 120.75(17)
C2 C3 C4 119.92(18)
C2 C3 H3A 120
C4 C3 H3A 120
O3 C4 C3 117.62(17)
O3 C4 C5 122.67(17)
C3 C4 C5 119.71(18)
C6 C5 C4 120.29(18)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 121.28(17)
C5 C6 H6 119.4
C1 C6 H6 119.4
O2 C7 O1 121.83(17)
O2 C7 C1 122.67(17)
O1 C7 C1 115.50(16)
C7 O1 H1 109.5
C4 O3 H3 109.5
C2 O4 H4 109.5
C9 C8 C12 117.57(17)
C9 C8 C13 123.21(17)
C12 C8 C13 119.21(16)
N2 C9 C8 123.77(18)
N2 C9 H9 118.1
C8 C9 H9 118.1
N2 C10 C11 123.45(19)
N2 C10 H10 118.3
C11 C10 H10 118.3
C12 C11 C10 118.45(19)
C12 C11 H11 120.8
C10 C11 H11 120.8
C11 C12 C8 119.54(18)
C11 C12 H12 120.2
C8 C12 H12 120.2
O5 C13 N1 121.67(17)
O5 C13 C8 119.57(17)
N1 C13 C8 118.76(16)
C13 N1 H1S 120
C13 N1 H1A 120
H1A N1 H1A 120
C9 N2 C10 117.19(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.394(3)
C1 C2 1.411(3)
C1 C7 1.458(3)
C2 O4 1.355(2)
C2 C3 1.380(3)
C3 C4 1.387(3)
C3 H3A 0.93
C4 O3 1.340(2)
C4 C5 1.397(3)
C5 C6 1.364(3)
C5 H5 0.93
C6 H6 0.93
C7 O2 1.237(2)
C7 O1 1.316(2)
O1 H1 0.82
O3 H3 0.82
O4 H4 0.82
C8 C9 1.385(3)
C8 C12 1.386(3)
C8 C13 1.494(3)
C9 N2 1.333(2)
C9 H9 0.93
C10 N2 1.336(3)
C10 C11 1.378(3)
C10 H10 0.93
C11 C12 1.375(3)
C11 H11 0.93
C12 H12 0.93
C13 O5 1.235(2)
C13 N1 1.328(2)
N1 H1S 0.86
N1 H1A 0.86
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 H1 O5 0.82 1.77 2.580(2) 167 .
O3 H3 N2 0.82 1.92 2.720(2) 166 1_544
O4 H4 O2 0.82 1.85 2.574(2) 147 .
N1 H1A O4 0.86 2.2 2.954(2) 146 2_566
N1 H1S O2 0.86 2.05 2.891(2) 166 .
C3 H3A O3 0.93 2.73 3.568(2) 151 2
C11 H11 O1 0.93 2.52 3.361(2) 151 2_776
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
C6 C1 C2 O4 178.83(18)
C7 C1 C2 O4 -0.8(3)
C6 C1 C2 C3 -0.2(3)
C7 C1 C2 C3 -179.74(18)
O4 C2 C3 C4 -178.48(18)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 O3 178.88(19)
C2 C3 C4 C5 -0.5(3)
O3 C4 C5 C6 -179.30(19)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 0.4(3)
C2 C1 C6 C5 -0.3(3)
C7 C1 C6 C5 179.27(19)
C6 C1 C7 O2 -179.49(19)
C2 C1 C7 O2 0.1(3)
C6 C1 C7 O1 0.2(3)
C2 C1 C7 O1 179.75(17)
C12 C8 C9 N2 0.1(3)
C13 C8 C9 N2 179.37(17)
N2 C10 C11 C12 -0.3(3)
C10 C11 C12 C8 -0.8(3)
C9 C8 C12 C11 0.9(3)
C13 C8 C12 C11 -178.38(18)
C9 C8 C13 O5 179.32(18)
C12 C8 C13 O5 -1.4(3)
C9 C8 C13 N1 -0.5(3)
C12 C8 C13 N1 178.76(18)
C8 C9 N2 C10 -1.2(3)
C11 C10 N2 C9 1.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146592
