#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/74/4507463.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_4507463
loop_
_publ_author_name
'Sarcevica, Inese'
'Orola, Liana'
'Veidis, Mikelis V.'
'Podjava, Anton'
'Belyakov, Sergey'
_publ_section_title
;
 Crystal and Molecular Structure and Stability of Isoniazid Cocrystals
 with Selected Carboxylic Acids
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1082
_journal_paper_doi               10.1021/cg301356h
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C10 H18 O4, 2(C6 H7 N3 O)'
_chemical_formula_sum            'C22 H32 N6 O6'
_chemical_formula_weight         476.54
_chemical_name_common            'isoniazid - sebacic acid cocrystal'
_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                104.455(4)
_cell_angle_beta                 92.400(3)
_cell_angle_gamma                95.106(4)
_cell_formula_units_Z            1
_cell_length_a                   6.8942(6)
_cell_length_b                   7.1004(6)
_cell_length_c                   12.4475(12)
_cell_measurement_reflns_used    11180
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     586.40(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       8
_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            4068
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             254.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0617
_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)+(0.0573P)²+0.1669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                1613
_reflns_number_total             2710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301356h_si_002.cif
_cod_data_source_block           isoniazid-sebacic-cocrystal
_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_database_code               4507463
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
O8 O 0.2384(3) 0.0578(2) 0.56819(16) 0.0529(5) Uani 1 1 d .
O12 O -0.4164(2) 0.9484(2) 0.78727(15) 0.0481(5) Uani 1 1 d .
O11 O -0.5466(2) 0.6783(2) 0.82743(15) 0.0461(5) Uani 1 1 d .
H11 H -0.432(5) 0.614(4) 0.794(3) 0.078(9) Uiso 1 1 d .
N1 N -0.2467(3) 0.5134(3) 0.73248(15) 0.0356(5) Uani 1 1 d .
C4 C 0.0670(3) 0.3381(3) 0.63115(17) 0.0320(5) Uani 1 1 d .
C3 C 0.0517(3) 0.5357(3) 0.64311(18) 0.0339(5) Uani 1 1 d .
H3 H 0.1462 0.6127 0.6176 0.041 Uiso 1 1 calc R
C16 C -0.8892(3) 1.2504(3) 0.95829(19) 0.0348(5) Uani 1 1 d .
H161 H -1.0054 1.1767 0.9165 0.042 Uiso 1 1 calc R
H162 H -0.8848 1.2238 1.0311 0.042 Uiso 1 1 calc R
N9 N 0.3556(3) 0.3359(3) 0.52852(16) 0.0407(5) Uani 1 1 d .
H9 H 0.3592 0.4690 0.5346 0.049 Uiso 1 1 d R
C15 C -0.7105(3) 1.1766(3) 0.89911(19) 0.0347(5) Uani 1 1 d .
H151 H -0.7146 1.1987 0.8253 0.042 Uiso 1 1 calc R
H152 H -0.5929 1.2488 0.9401 0.042 Uiso 1 1 calc R
C7 C 0.2288(3) 0.2306(3) 0.57337(18) 0.0352(5) Uani 1 1 d .
C14 C -0.7053(3) 0.9597(3) 0.89025(19) 0.0354(5) Uani 1 1 d .
H141 H -0.6991 0.9411 0.9649 0.043 Uiso 1 1 calc R
H142 H -0.8273 0.8913 0.8529 0.043 Uiso 1 1 calc R
C2 C -0.1077(3) 0.6155(3) 0.69385(19) 0.0357(5) Uani 1 1 d .
H2 H -0.1180 0.7478 0.7013 0.043 Uiso 1 1 calc R
C13 C -0.5404(3) 0.8653(3) 0.82997(18) 0.0339(5) Uani 1 1 d .
C17 C -0.9070(3) 1.4670(3) 0.97292(19) 0.0360(6) Uani 1 1 d .
H171 H -0.9052 1.4956 0.9007 0.043 Uiso 1 1 calc R
H172 H -0.7947 1.5417 1.0184 0.043 Uiso 1 1 calc R
C5 C -0.0764(3) 0.2315(3) 0.67158(19) 0.0372(6) Uani 1 1 d .
H5 H -0.0700 0.0989 0.6651 0.045 Uiso 1 1 calc R
N10 N 0.5133(3) 0.2583(3) 0.46835(17) 0.0424(5) Uani 1 1 d .
H101 H 0.5842 0.1953 0.5011 0.051 Uiso 1 1 d R
H102 H 0.4686 0.1582 0.4020 0.051 Uiso 1 1 d R
C6 C -0.2304(3) 0.3240(3) 0.72210(19) 0.0374(6) Uani 1 1 d .
H6 H -0.3258 0.2512 0.7497 0.045 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
_geom_angle_site_symmetry_3
C13 O11 H11 114.0(17) . .
C2 N1 C6 117.89(18) . .
C5 C4 C3 118.24(19) . .
C5 C4 C7 117.79(19) . .
C3 C4 C7 123.9(2) . .
C2 C3 C4 118.5(2) . .
C2 C3 H3 120.8 . .
C4 C3 H3 120.8 . .
C17 C16 C15 114.76(18) . .
C17 C16 H161 108.6 . .
C15 C16 H161 108.6 . .
C17 C16 H162 108.6 . .
C15 C16 H162 108.6 . .
H161 C16 H162 107.6 . .
C7 N9 N10 123.53(18) . .
C7 N9 H9 126.1 . .
N10 N9 H9 110.3 . .
C14 C15 C16 110.45(18) . .
C14 C15 H151 109.6 . .
C16 C15 H151 109.6 . .
C14 C15 H152 109.6 . .
C16 C15 H152 109.6 . .
H151 C15 H152 108.1 . .
O8 C7 N9 123.2(2) . .
O8 C7 C4 121.1(2) . .
N9 C7 C4 115.69(19) . .
C13 C14 C15 116.31(18) . .
C13 C14 H141 108.2 . .
C15 C14 H141 108.2 . .
C13 C14 H142 108.2 . .
C15 C14 H142 108.2 . .
H141 C14 H142 107.4 . .
N1 C2 C3 123.6(2) . .
N1 C2 H2 118.2 . .
C3 C2 H2 118.2 . .
O12 C13 O11 123.12(19) . .
O12 C13 C14 124.8(2) . .
O11 C13 C14 112.03(18) . .
C16 C17 C17 113.2(2) . 2_387
C16 C17 H171 108.9 . .
C17 C17 H171 108.9 2_387 .
C16 C17 H172 108.9 . .
C17 C17 H172 108.9 2_387 .
H171 C17 H172 107.8 . .
C4 C5 C6 119.4(2) . .
C4 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
N9 N10 H101 115.0 . .
N9 N10 H102 111.9 . .
H101 N10 H102 100.5 . .
N1 C6 C5 122.4(2) . .
N1 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O8 C7 1.221(3) .
O12 C13 1.211(3) .
O11 C13 1.317(3) .
O11 H11 1.00(3) .
N1 C2 1.328(3) .
N1 C6 1.334(3) .
C4 C5 1.379(3) .
C4 C3 1.387(3) .
C4 C7 1.513(3) .
C3 C2 1.385(3) .
C3 H3 0.9300 .
C16 C17 1.520(3) .
C16 C15 1.527(3) .
C16 H161 0.9700 .
C16 H162 0.9700 .
N9 C7 1.330(3) .
N9 N10 1.419(2) .
N9 H9 0.9268 .
C15 C14 1.520(3) .
C15 H151 0.9700 .
C15 H152 0.9700 .
C14 C13 1.504(3) .
C14 H141 0.9700 .
C14 H142 0.9700 .
C2 H2 0.9300 .
C17 C17 1.529(4) 2_387
C17 H171 0.9700 .
C17 H172 0.9700 .
C5 C6 1.388(3) .
C5 H5 0.9300 .
N10 H101 0.8478 .
N10 H102 0.9636 .
C6 H6 0.9300 .
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
C5 C4 C3 C2 -0.7(3) .
C7 C4 C3 C2 177.5(2) .
C17 C16 C15 C14 179.2(2) .
N10 N9 C7 O8 1.1(4) .
N10 N9 C7 C4 -178.10(19) .
C5 C4 C7 O8 -4.1(3) .
C3 C4 C7 O8 177.8(2) .
C5 C4 C7 N9 175.2(2) .
C3 C4 C7 N9 -3.0(3) .
C16 C15 C14 C13 177.90(19) .
C6 N1 C2 C3 0.4(3) .
C4 C3 C2 N1 0.4(4) .
C15 C14 C13 O12 -1.4(4) .
C15 C14 C13 O11 179.3(2) .
C15 C16 C17 C17 177.0(2) 2_387
C3 C4 C5 C6 0.2(3) .
C7 C4 C5 C6 -178.1(2) .
C2 N1 C6 C5 -0.9(3) .
C4 C5 C6 N1 0.6(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146419
