Cocrystals of zileuton with enhanced physical stability
Chen, Xin; Li, Duanxiu; Luo, Chun; Wang, Jinqiu; Deng, Zongwu; Zhang, Hailu; CrystEngComm 20 (2018) 990–; doi:10.1039/C7CE02150J

data_7229953
_publ_section_title
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 Cocrystals of zileuton with enhanced physical stability
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              990
_journal_paper_doi               10.1039/C7CE02150J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C11 H12 N2 O2 S, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C23 H24 N6 O4 S'
_chemical_formula_weight         480.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2017-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.691(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1859(7)
_cell_length_b                   43.799(5)
_cell_length_c                   10.7366(15)
_cell_measurement_reflns_used    1855
_cell_measurement_temperature    213.0
_cell_measurement_theta_max      22.8460
_cell_measurement_theta_min      4.0170
_cell_volume                     2359.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      213.0
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   20.00   85.25   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   57.0000    0.0000 87

  2 omega  -39.00   39.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428  -37.0000 -150.0000 104

  3 omega   27.00   52.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428   19.0000    0.0000 34

  4 omega  -47.00  -11.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2428  -37.0000 -180.0000 48

  5 omega  -25.00    0.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -99.0000   90.0000 34

  6 omega  -17.00   16.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.1803  -87.0000  132.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0472865000
_diffrn_orient_matrix_UB_12      -0.0142515000
_diffrn_orient_matrix_UB_13      0.0169984000
_diffrn_orient_matrix_UB_21      -0.0578927000
_diffrn_orient_matrix_UB_22      -0.0029818000
_diffrn_orient_matrix_UB_23      -0.0658380000
_diffrn_orient_matrix_UB_31      0.1189826000
_diffrn_orient_matrix_UB_32      -0.0070970000
_diffrn_orient_matrix_UB_33      -0.0065852000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.1022
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14099
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rodlike
_exptl_crystal_F_000             1008
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0057(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.0882
_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/[\s^2^(Fo^2^)+(0.0940P)^2^+1.9215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2634
_reflns_number_gt                2415
_reflns_number_total             4806
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce02150j2.cif
_cod_data_source_block           g170904a
_cod_depositor_comments
'Adding full bibliography for 7229950--7229953.cif.'
_cod_database_code               7229953
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 98.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 C8, C7, C6, C5, C4, C3, C2, C1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C8 \\sim C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C1: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.004
4.a Rotating group:
 N5(H5A,H5B)
4.b Ternary CH refined with riding coordinates:
 C9(H9)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C3(H3), C2(H2), C17(H17), C16(H16), C15(H15),
 C14(H14), C23(H23), C22(H22), C21(H21), C20(H20)
4.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'