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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/7/22/66/7226677.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_7226677
loop_
_publ_author_name
'Saikia, Basanta'
'Khatioda, Rajiv'
'Bora, Pranita'
'Sarma, Bipul'
_publ_section_title
;
 Pyridine N-oxides as coformers in the development of drug cocrystals
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              8454
_journal_paper_doi               10.1039/C6CE01838F
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C24 H22 N4 O6'
_chemical_formula_weight         462.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2016-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.977(3)
_cell_length_b                   12.112(4)
_cell_length_c                   16.439(5)
_cell_measurement_reflns_used    549
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.19
_cell_measurement_theta_min      2.79
_cell_volume                     2185.6(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.558
_diffrn_measured_fraction_theta_max 0.640
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.558
_diffrn_reflns_Laue_measured_fraction_max 0.640
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1902
_diffrn_reflns_point_group_measured_fraction_full 0.558
_diffrn_reflns_point_group_measured_fraction_max 0.640
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.003
_diffrn_reflns_theta_min         2.794
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Metahnol'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.979
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                833
_reflns_number_total             1102
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01838f2.cif
_cod_data_source_block           BS_RK_NC_2_0m
_cod_depositor_comments
'Adding full bibliography for 7226673--7226678.cif.'
_cod_original_cell_volume        2185.5(11)
_cod_database_code               7226677
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.0043(2) 0.94659(17) 0.29383(17) 0.0281(8) Uani 1 1 d . .
C2 C -0.0637(3) 0.9072(2) 0.0826(2) 0.0189(10) Uani 1 1 d . .
H2 H -0.1093 0.8588 0.0509 0.023 Uiso 1 1 calc R U
N2 N 0.3796(3) 0.3303(2) 0.6821(2) 0.0271(9) Uani 1 1 d . .
O4 O 0.1346(2) 0.02815(16) 0.41062(17) 0.0241(7) Uani 1 1 d . .
C7 C 0.2535(3) 0.1903(2) 0.6198(2) 0.0216(10) Uani 1 1 d . .
H7 H 0.2264 0.1680 0.6708 0.026 Uiso 1 1 calc R U
O3 O 0.2255(2) 0.15268(18) 0.32926(17) 0.0259(7) Uani 1 1 d . .
N1 N 0.0041(2) 0.9621(2) 0.2142(2) 0.0205(8) Uani 1 1 d . .
C1 C -0.0614(3) 0.8927(2) 0.1654(3) 0.0215(10) Uani 1 1 d . .
H1 H -0.1050 0.8349 0.1886 0.026 Uiso 1 1 calc R U
C3 C 0.0003(3) 0.9927(2) 0.0444(2) 0.0186(9) Uani 1 1 d . .
C5 C 0.0669(3) 1.0473(2) 0.1791(3) 0.0239(10) Uani 1 1 d . .
H5 H 0.1115 1.0952 0.2117 0.029 Uiso 1 1 calc R U
C4 C 0.0649(3) 1.0630(2) 0.0969(2) 0.0216(10) Uani 1 1 d . .
H4 H 0.1077 1.1222 0.0750 0.026 Uiso 1 1 calc R U
C6 C 0.3371(3) 0.2785(2) 0.6132(3) 0.0198(10) Uani 1 1 d . .
C11 C 0.3765(3) 0.3095(2) 0.5352(2) 0.0190(10) Uani 1 1 d . .
H11 H 0.4321 0.3669 0.5298 0.023 Uiso 1 1 calc R U
C10 C 0.3347(3) 0.2568(2) 0.4671(2) 0.0186(9) Uani 1 1 d . .
H10 H 0.3621 0.2793 0.4162 0.022 Uiso 1 1 calc R U
C9 C 0.2505(3) 0.1687(2) 0.4730(2) 0.0167(9) Uani 1 1 d . .
C12 C 0.2046(3) 0.1170(2) 0.3976(3) 0.0188(10) Uani 1 1 d . .
C8 C 0.2118(3) 0.1370(2) 0.5508(2) 0.0212(10) Uani 1 1 d . .
H8 H 0.1570 0.0789 0.5562 0.025 Uiso 1 1 calc R U
H2A H 0.411(3) 0.394(3) 0.671(2) 0.058(14) Uiso 1 1 d . .
H1A H 0.341(4) 0.316(4) 0.731(3) 0.085(19) Uiso 1 1 d . .
H3A H 0.107(4) 0.005(3) 0.361(3) 0.068(17) Uiso 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 0.0000 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_3
C1 C2 C3 122.0(3) .
C1 C2 H2 119.0 .
C3 C2 H2 119.0 .
C6 N2 H2A 111(3) .
C6 N2 H1A 118(3) .
H2A N2 H1A 123(4) .
C12 O4 H3A 107(3) .
C8 C7 C6 120.3(3) .
C8 C7 H7 119.8 .
C6 C7 H7 119.8 .
O1 N1 C5 121.6(3) .
O1 N1 C1 119.6(3) .
C5 N1 C1 118.8(3) .
N1 C1 C2 120.8(3) .
N1 C1 H1 119.6 .
C2 C1 H1 119.6 .
C2 C3 C4 115.2(3) .
C2 C3 C3 122.2(4) 5_575
C4 C3 C3 122.6(4) 5_575
N1 C5 C4 121.0(3) .
N1 C5 H5 119.5 .
C4 C5 H5 119.5 .
C5 C4 C3 122.1(3) .
C5 C4 H4 118.9 .
C3 C4 H4 118.9 .
N2 C6 C11 121.7(3) .
N2 C6 C7 120.0(4) .
C11 C6 C7 118.2(3) .
C10 C11 C6 121.4(3) .
C10 C11 H11 119.3 .
C6 C11 H11 119.3 .
C11 C10 C9 121.0(3) .
C11 C10 H10 119.5 .
C9 C10 H10 119.5 .
C8 C9 C10 117.8(3) .
C8 C9 C12 123.2(3) .
C10 C9 C12 119.0(3) .
O3 C12 O4 122.5(3) .
O3 C12 C9 123.8(3) .
O4 C12 C9 113.7(3) .
C7 C8 C9 121.4(3) .
C7 C8 H8 119.3 .
C9 C8 H8 119.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.323(4) .
C2 C1 1.374(5) .
C2 C3 1.399(4) .
C2 H2 0.9300 .
N2 C6 1.377(4) .
N2 H2A 0.87(4) .
N2 H1A 0.92(5) .
O4 C12 1.340(4) .
O4 H3A 0.92(5) .
C7 C8 1.383(4) .
C7 C6 1.412(4) .
C7 H7 0.9300 .
O3 C12 1.225(4) .
N1 C5 1.369(4) .
N1 C1 1.366(4) .
C1 H1 0.9300 .
C3 C4 1.406(4) .
C3 C3 1.470(7) 5_575
C5 C4 1.363(4) .
C5 H5 0.9300 .
C4 H4 0.9300 .
C6 C11 1.403(5) .
C11 C10 1.367(4) .
C11 H11 0.9300 .
C10 C9 1.416(4) .
C10 H10 0.9300 .
C9 C8 1.402(4) .
C9 C12 1.476(5) .
C8 H8 0.9300 .
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
N2 H1A O3 0.92(5) 2.09(5) 2.958(5) 156(4) 7_566
N2 H2A O1 0.87(4) 2.26(4) 3.055(4) 152(4) 2_566
C5 H5 O3 0.93 2.40 3.280(5) 156.7 1_565
C1 H1 O3 0.93 2.59 3.421(4) 149.1 3
C5 H5 O3 0.93 2.40 3.280(5) 156.7 1_565
C1 H1 O3 0.93 2.59 3.421(4) 149.1 3
C1 H1 O3 0.93 2.59 3.421(4) 149.1 3
C5 H5 O3 0.93 2.40 3.280(5) 156.7 1_565
C1 H1 O3 0.93 2.59 3.421(4) 149.1 3
C5 H5 O3 0.93 2.40 3.280(5) 156.7 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_1
_geom_torsion_site_symmetry_4
O1 N1 C1 C2 179.6(3) . .
C5 N1 C1 C2 0.6(4) . .
C3 C2 C1 N1 0.1(5) . .
C1 C2 C3 C4 -1.1(4) . .
C1 C2 C3 C3 178.9(3) . 5_575
O1 N1 C5 C4 -179.3(3) . .
C1 N1 C5 C4 -0.3(4) . .
N1 C5 C4 C3 -0.8(5) . .
C2 C3 C4 C5 1.4(5) . .
C3 C3 C4 C5 -178.6(3) 5_575 .
C8 C7 C6 N2 -179.2(3) . .
C8 C7 C6 C11 -0.3(5) . .
N2 C6 C11 C10 179.4(3) . .
C7 C6 C11 C10 0.6(5) . .
C6 C11 C10 C9 -0.3(5) . .
C11 C10 C9 C8 -0.2(4) . .
C11 C10 C9 C12 177.8(3) . .
C8 C9 C12 O3 170.4(3) . .
C10 C9 C12 O3 -7.6(5) . .
C8 C9 C12 O4 -7.9(4) . .
C10 C9 C12 O4 174.1(3) . .
C6 C7 C8 C9 -0.2(5) . .
C10 C9 C8 C7 0.5(4) . .
C12 C9 C8 C7 -177.5(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 85836976
