#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/66/7226673.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_7226673
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            'C15 H14 N O5'
_chemical_formula_weight         288.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.789(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1347(4)
_cell_length_b                   10.8799(5)
_cell_length_c                   12.0819(5)
_cell_measurement_reflns_used    1840
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.54
_cell_volume                     1304.10(10)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12426
_diffrn_reflns_theta_full        28.73
_diffrn_reflns_theta_max         28.73
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.804
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0527
_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+0.8447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1603
_reflns_number_gt                2223
_reflns_number_total             3330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce01838f2.cif
_cod_data_source_block           bs_bpf_3_0m
_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_cell_volume        1304.11(10)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7226673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.34786(14) 0.99038(16) 0.12071(14) 0.0208(4) Uani 1 1 d .
C3 C 0.07338(16) 0.99893(17) 0.02478(15) 0.0168(4) Uani 1 1 d .
C5 C 0.26218(18) 1.04575(19) 0.17588(17) 0.0228(4) Uani 1 1 d .
H5 H 0.2949 1.0809 0.2463 0.027 Uiso 1 1 calc R
C4 C 0.12586(18) 1.05124(19) 0.12944(17) 0.0213(4) Uani 1 1 d .
H4 H 0.0683 1.0906 0.1689 0.026 Uiso 1 1 calc R
C2 C 0.16618(18) 0.94432(19) -0.03060(17) 0.0235(4) Uani 1 1 d .
H2 H 0.1360 0.9090 -0.1013 0.028 Uiso 1 1 calc R
C1 C 0.30185(19) 0.9416(2) 0.01728(17) 0.0254(5) Uani 1 1 d .
H1 H 0.3620 0.9059 -0.0219 0.031 Uiso 1 1 calc R
O4 O -0.15380(14) 0.40367(15) 0.09813(12) 0.0270(4) Uani 1 1 d .
O3 O -0.23696(12) 0.25506(14) 0.24594(12) 0.0265(4) Uani 1 1 d .
C12 C -0.00404(17) 0.22630(18) 0.35106(16) 0.0186(4) Uani 1 1 d .
H12 H -0.0299 0.1749 0.4043 0.022 Uiso 1 1 calc R
C7 C -0.10074(17) 0.27459(18) 0.26374(16) 0.0190(4) Uani 1 1 d .
C8 C -0.06240(17) 0.35321(19) 0.18394(17) 0.0206(4) Uani 1 1 d .
C9 C 0.07271(18) 0.38202(18) 0.19279(17) 0.0212(4) Uani 1 1 d .
H9 H 0.0986 0.4343 0.1401 0.025 Uiso 1 1 calc R
C10 C 0.16948(17) 0.33334(19) 0.27974(16) 0.0206(4) Uani 1 1 d .
H10 H 0.2597 0.3534 0.2848 0.025 Uiso 1 1 calc R
C11 C 0.13335(17) 0.25496(18) 0.35933(16) 0.0190(4) Uani 1 1 d .
C13 C 0.23281(17) 0.20219(18) 0.45192(17) 0.0206(4) Uani 1 1 d .
H13 H 0.1994 0.1612 0.5079 0.025 Uiso 1 1 calc R
C15 C 0.46064(17) 0.1467(2) 0.55711(17) 0.0238(4) Uani 1 1 d .
C14 C 0.36743(18) 0.2068(2) 0.46439(17) 0.0245(4) Uani 1 1 d .
H14 H 0.4033 0.2505 0.4113 0.029 Uiso 1 1 calc R
C16 C -0.28799(18) 0.1739(2) 0.31932(19) 0.0269(5) Uani 1 1 d .
H16A H -0.2526 0.0929 0.3133 0.040 Uiso 1 1 calc R
H16B H -0.3846 0.1716 0.2984 0.040 Uiso 1 1 calc R
H16C H -0.2613 0.2023 0.3958 0.040 Uiso 1 1 calc R
O5 O 0.47788(12) 0.98395(15) 0.16661(12) 0.0288(4) Uani 1 1 d .
O7 O 0.40594(14) 0.11077(16) 0.64175(13) 0.0316(4) Uani 1 1 d .
O6 O 0.57907(13) 0.13075(16) 0.55436(14) 0.0347(4) Uani 1 1 d .
H4A H 0.465(3) 0.074(3) 0.699(3) 0.067(10) Uiso 1 1 d .
H3A H -0.239(3) 0.384(3) 0.104(3) 0.061(9) 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
O5 N1 C5 120.41(16) .
O5 N1 C1 119.55(16) .
C5 N1 C1 120.04(16) .
C4 C3 C2 116.17(16) .
C4 C3 C3 121.7(2) 3_575
C2 C3 C3 122.1(2) 3_575
N1 C5 C4 120.85(18) .
C5 C4 C3 121.11(18) .
C1 C2 C3 121.39(18) .
N1 C1 C2 120.40(19) .
C7 O3 C16 118.80(15) .
C7 C12 C11 120.25(18) .
O3 C7 C12 126.38(18) .
O3 C7 C8 113.50(16) .
C12 C7 C8 120.11(16) .
O4 C8 C9 118.45(18) .
O4 C8 C7 122.03(16) .
C9 C8 C7 119.52(17) .
C10 C9 C8 120.39(18) .
C9 C10 C11 120.86(17) .
C10 C11 C12 118.86(17) .
C10 C11 C13 122.20(16) .
C12 C11 C13 118.94(17) .
C14 C13 C11 126.67(19) .
O6 C15 O7 123.42(19) .
O6 C15 C14 121.8(2) .
O7 C15 C14 114.74(16) .
C13 C14 C15 123.45(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O5 1.3230(18) .
N1 C5 1.341(3) .
N1 C1 1.350(2) .
C3 C4 1.390(3) .
C3 C2 1.394(3) .
C3 C3 1.486(3) 3_575
C5 C4 1.382(2) .
C2 C1 1.379(2) .
O4 C8 1.357(2) .
O3 C7 1.370(2) .
O3 C16 1.422(2) .
C12 C7 1.388(2) .
C12 C11 1.410(2) .
C7 C8 1.402(3) .
C8 C9 1.387(2) .
C9 C10 1.387(3) .
C10 C11 1.389(3) .
C11 C13 1.462(3) .
C13 C14 1.343(2) .
C15 O6 1.220(2) .
C15 O7 1.318(3) .
C15 C14 1.464(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202795
