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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/58/7225826.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_7225826
loop_
_publ_author_name
'de Melo, Cristiane C.'
'de Sousa Carvalho, Paulo'
'Diniz, Luan F.'
'D'Vries, Richard F.'
'Ayala, Alejandro P.'
'Ellena, Javier'
_publ_section_title
;
 Supramolecular synthesis and thermochemical investigations of
 pharmaceutical inorganic isoniazid salts
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              6378
_journal_paper_doi               10.1039/C6CE00969G
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H8 N3 O, N O3'
_chemical_formula_sum            'C6 H8 N4 O4'
_chemical_formula_weight         200.16
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-04-14T06:18:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-04-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.151(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3630(13)
_cell_length_b                   15.970(6)
_cell_length_c                   8.043(2)
_cell_measurement_reflns_used    771
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_measurement_wavelength     0.71073
_cell_volume                     816.7(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0331356
_diffrn_orient_matrix_UB_12      -0.0229982
_diffrn_orient_matrix_UB_13      0.111657
_diffrn_orient_matrix_UB_21      0.153174
_diffrn_orient_matrix_UB_22      0
_diffrn_orient_matrix_UB_23      0.0327152
_diffrn_orient_matrix_UB_31      -0.013085
_diffrn_orient_matrix_UB_32      0.058239
_diffrn_orient_matrix_UB_33      0.0440926
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1462
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_min         3.449
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.062(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1454
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0781P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                1183
_reflns_number_total             1454
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00969g2.cif
_cod_data_source_block           isonitrate
_cod_depositor_comments
'Adding full bibliography for 7225824--7225827.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7225826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
O3 0.0830(6) 0.2894(3) 0.2428(5) 0.0700(11) Uani d 1 O
O1 0.6802(6) -0.0030(3) 0.3215(6) 0.0750(12) Uani d 1 O
N1 0.6155(6) 0.1263(3) 0.4177(5) 0.0611(11) Uani d 1 N
N2 0.0468(6) -0.0538(3) 0.6410(5) 0.0569(11) Uani d 1 N
O2 0.4184(6) 0.2891(3) 0.2143(6) 0.0826(13) Uani d 1 O
N4 0.2657(7) 0.2842(3) 0.3064(5) 0.0584(11) Uani d 1 N
C1 0.3894(7) 0.0123(3) 0.4942(6) 0.0495(11) Uani d 1 C
C6 0.2390(7) 0.0646(3) 0.5628(6) 0.0564(12) Uani d 1 C
H6 0.2535 0.1225 0.5583 0.068 Uiso calc 1 H
C4 0.1870(8) -0.1058(3) 0.5752(7) 0.0603(13) Uani d 1 C
H4 0.168 -0.1634 0.5809 0.072 Uiso calc 1 H
C2 0.5772(7) 0.0452(3) 0.4051(6) 0.0526(11) Uani d 1 C
C3 0.3591(7) -0.0732(3) 0.4992(6) 0.0578(12) Uani d 1 C
H3 0.4551 -0.1089 0.4511 0.069 Uiso calc 1 H
O4 0.2913(7) 0.2733(3) 0.4567(5) 0.0915(14) Uani d 1 O
C5 0.0700(8) 0.0293(3) 0.6367(6) 0.0598(12) Uani d 1 C
H5 -0.0296 0.0634 0.6843 0.072 Uiso calc 1 H
N3 0.7840(6) 0.1608(3) 0.3313(5) 0.0606(12) Uani d 1 N
H3B 0.8629 0.183 0.4154 0.073 Uiso d 1 H
H3A 0.7388 0.1987 0.2472 0.073 Uiso d 1 H
H1 0.5374 0.1541 0.4707 0.073 Uiso d 1 H
H2 -0.0774 -0.0805 0.7263 0.073 Uiso d 1 H
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
-1 0 -2 0.055
1 0 2 0.07
-1 0 1 0.252
3 0 -4 0.16
0 -1 0 0.011
0 1 0 0.015
-1 -1 16 0.15
-1 0 2 0.214
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 N3 119.1(4)
C5 N2 C4 121.9(4)
O4 N4 O2 121.2(5)
O4 N4 O3 119.9(4)
O2 N4 O3 119.0(4)
C3 C1 C6 118.8(4)
C3 C1 C2 118.1(4)
C6 C1 C2 123.0(4)
C5 C6 C1 119.0(5)
N2 C4 C3 119.6(5)
O1 C2 N1 123.8(5)
O1 C2 C1 119.4(4)
N1 C2 C1 116.8(4)
C4 C3 C1 120.0(4)
N2 C5 C6 120.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 N4 1.255(6)
O1 C2 1.227(6)
N1 C2 1.322(6)
N1 N3 1.412(5)
N2 C5 1.335(7)
N2 C4 1.341(7)
O2 N4 1.246(6)
N4 O4 1.226(5)
C1 C3 1.381(7)
C1 C6 1.399(7)
C1 C2 1.511(7)
C6 C5 1.370(7)
C4 C3 1.376(7)
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
C3 C1 C6 C5 1.9(7)
C2 C1 C6 C5 178.1(4)
C5 N2 C4 C3 -0.7(8)
N3 N1 C2 O1 -0.1(8)
N3 N1 C2 C1 -177.3(4)
C3 C1 C2 O1 9.9(7)
C6 C1 C2 O1 -166.2(5)
C3 C1 C2 N1 -172.7(4)
C6 C1 C2 N1 11.1(7)
N2 C4 C3 C1 1.4(8)
C6 C1 C3 C4 -2.0(7)
C2 C1 C3 C4 -178.3(4)
C4 N2 C5 C6 0.7(8)
C1 C6 C5 N2 -1.3(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202364
