#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/66/7226674.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_7226674
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            'C13 H13 N O3'
_chemical_formula_weight         231.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-26 deposited with the CCDC.
2016-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.620(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6691(9)
_cell_length_b                   6.8681(5)
_cell_length_c                   14.3968(9)
_cell_measurement_reflns_used    1293
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.45
_cell_measurement_theta_min      2.36
_cell_volume                     1148.28(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8593
_diffrn_reflns_theta_full        26.19
_diffrn_reflns_theta_max         26.19
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             506
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0524
_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)+(0.1000P)²+0.3734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                1213
_reflns_number_total             2274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01838f2.cif
_cod_data_source_block           bs_acrno_1_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226673--7226678.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7226674
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.61051(14) 0.3617(2) 0.28193(11) 0.0448(5) Uani 1 1 d .
O1 O 0.49704(13) 0.3644(2) 0.27274(12) 0.0709(5) Uani 1 1 d .
O2 O 0.3736(2) 0.7001(3) 0.21496(14) 0.0737(6) Uani 1 1 d .
O3 O 0.35254(16) 1.0615(4) 0.30957(13) 0.0761(6) Uani 1 1 d .
C9 C 0.66827(17) 0.3620(3) 0.20357(12) 0.0413(5) Uani 1 1 d .
C8 C 0.79030(17) 0.3627(3) 0.21264(13) 0.0428(5) Uani 1 1 d .
C5 C 0.79007(18) 0.3609(3) 0.37999(12) 0.0445(5) Uani 1 1 d .
C6 C 0.66820(18) 0.3594(3) 0.36952(13) 0.0438(5) Uani 1 1 d .
C7 C 0.84947(17) 0.3623(3) 0.30126(14) 0.0459(5) Uani 1 1 d .
H7 H 0.9296 0.3630 0.3077 0.055 Uiso 1 1 calc R
C10 C 0.6053(2) 0.3633(3) 0.11451(14) 0.0558(6) Uani 1 1 d .
H10 H 0.5252 0.3644 0.1089 0.067 Uiso 1 1 calc R
C13 C 0.8465(2) 0.3636(3) 0.12850(15) 0.0572(6) Uani 1 1 d .
H13 H 0.9265 0.3641 0.1318 0.069 Uiso 1 1 calc R
C1 C 0.6049(2) 0.3554(3) 0.44905(16) 0.0638(7) Uani 1 1 d .
H1 H 0.5248 0.3533 0.4420 0.077 Uiso 1 1 calc R
C4 C 0.8457(2) 0.3605(3) 0.47292(15) 0.0636(7) Uani 1 1 d .
H4 H 0.9256 0.3625 0.4824 0.076 Uiso 1 1 calc R
C11 C 0.6634(3) 0.3629(4) 0.03742(15) 0.0680(8) Uani 1 1 d .
H11 H 0.6222 0.3619 -0.0212 0.082 Uiso 1 1 calc R
C12 C 0.7834(3) 0.3638(3) 0.04384(15) 0.0681(8) Uani 1 1 d .
H12 H 0.8208 0.3645 -0.0103 0.082 Uiso 1 1 calc R
C3 C 0.7832(3) 0.3572(4) 0.54743(16) 0.0793(9) Uani 1 1 d .
H3 H 0.8208 0.3565 0.6075 0.095 Uiso 1 1 calc R
C2 C 0.6631(3) 0.3548(4) 0.53508(17) 0.0796(9) Uani 1 1 d .
H2 H 0.6221 0.3527 0.5873 0.096 Uiso 1 1 calc R
H1B H 0.369(3) 0.953(6) 0.278(2) 0.131(15) Uiso 1 1 d .
H1A H 0.405(3) 1.150(4) 0.2959(19) 0.085(9) Uiso 1 1 d .
H2A H 0.413(3) 0.606(5) 0.2344(19) 0.091(11) Uiso 1 1 d .
H2B H 0.295(3) 0.650(4) 0.2071(18) 0.098(10) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0417(10) 0.0405(11) 0.0525(9) 0.0045(8) 0.0062(8) 0.0019(8)
O1 0.0401(9) 0.0745(12) 0.0986(12) 0.0164(9) 0.0086(8) 0.0011(8)
O2 0.0613(13) 0.0709(14) 0.0896(13) 0.0067(11) 0.0105(10) 0.0020(11)
O3 0.0608(12) 0.0815(16) 0.0875(13) 0.0020(12) 0.0152(9) -0.0084(11)
C9 0.0517(13) 0.0285(11) 0.0434(10) 0.0016(8) 0.0032(9) -0.0002(9)
C8 0.0487(13) 0.0313(12) 0.0495(11) -0.0009(9) 0.0100(9) -0.0003(9)
C5 0.0551(14) 0.0327(12) 0.0448(11) -0.0011(9) 0.0002(9) 0.0020(10)
C6 0.0549(14) 0.0316(12) 0.0461(11) 0.0018(9) 0.0111(9) 0.0044(10)
C7 0.0390(12) 0.0413(13) 0.0570(12) -0.0013(10) 0.0022(9) 0.0021(9)
C10 0.0672(16) 0.0437(14) 0.0532(12) 0.0020(10) -0.0110(11) -0.0004(11)
C13 0.0694(16) 0.0459(14) 0.0605(13) -0.0013(10) 0.0266(12) 0.0011(11)
C1 0.0790(17) 0.0527(16) 0.0640(14) 0.0040(11) 0.0291(12) 0.0072(12)
C4 0.0817(18) 0.0504(15) 0.0544(13) -0.0014(10) -0.0152(12) 0.0034(13)
C11 0.107(2) 0.0517(16) 0.0421(12) 0.0004(10) -0.0063(13) -0.0004(15)
C12 0.115(2) 0.0466(16) 0.0466(12) -0.0002(10) 0.0271(14) 0.0016(15)
C3 0.135(3) 0.0609(19) 0.0393(12) -0.0013(11) -0.0044(14) 0.0109(18)
C2 0.129(3) 0.0647(19) 0.0497(14) 0.0035(12) 0.0306(16) 0.0147(17)
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
O1 N1 C9 119.20(16)
O1 N1 C6 119.40(16)
C9 N1 C6 121.40(17)
N1 C9 C10 119.54(19)
N1 C9 C8 119.68(17)
C10 C9 C8 120.78(18)
C7 C8 C9 119.27(17)
C7 C8 C13 123.29(19)
C9 C8 C13 117.44(18)
C7 C5 C6 119.41(17)
C7 C5 C4 123.3(2)
C6 C5 C4 117.32(19)
N1 C6 C5 119.72(17)
N1 C6 C1 119.6(2)
C5 C6 C1 120.7(2)
C5 C7 C8 120.51(19)
C11 C10 C9 119.0(2)
C12 C13 C8 120.4(2)
C2 C1 C6 118.9(3)
C3 C4 C5 120.8(2)
C10 C11 C12 121.7(2)
C13 C12 C11 120.7(2)
C4 C3 C2 120.7(2)
C1 C2 C3 121.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.318(2)
N1 C9 1.370(2)
N1 C6 1.370(2)
C9 C10 1.414(3)
C9 C8 1.417(3)
C8 C7 1.390(3)
C8 C13 1.433(3)
C5 C7 1.385(3)
C5 C6 1.415(3)
C5 C4 1.429(3)
C6 C1 1.422(3)
C10 C11 1.356(3)
C13 C12 1.360(3)
C1 C2 1.353(4)
C4 C3 1.355(3)
C11 C12 1.394(4)
C3 C2 1.395(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202796
