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_7229952
_publ_section_title
;
 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, C6 H6 N2 O'
_chemical_formula_sum            'C17 H18 N4 O3 S'
_chemical_formula_weight         358.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-12-05 deposited with the CCDC.
2018-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                75.429(15)
_cell_angle_beta                 74.117(15)
_cell_angle_gamma                79.223(16)
_cell_formula_units_Z            4
_cell_length_a                   10.2301(19)
_cell_length_b                   10.609(2)
_cell_length_c                   17.283(3)
_cell_measurement_reflns_used    1028
_cell_measurement_temperature    213.50(10)
_cell_measurement_theta_max      73.7090
_cell_measurement_theta_min      4.3130
_cell_volume                     1732.0(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      213.50(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   37.0000 -180.0000 82

  2 omega  -96.00    3.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093  125.0000   60.0000 99

  3 omega  -69.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   57.0000    0.0000 101

  4 omega -111.00  -20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093  -57.0000 -150.0000 91

  5 omega  -43.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0093   37.0000  120.0000 58

  6 omega   42.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000 -150.0000 55

  7 omega   24.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000  -30.0000 74

  8 omega   35.00   92.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000  120.0000 57

  9 omega   54.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -45.0000    0.0000 45

 10 omega  105.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  125.0000    0.0000 71

 11 omega   38.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000  120.0000 71

 12 omega   30.00   63.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -30.0000  150.0000 33

 13 omega   38.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -94.0000   30.0000 65

 14 omega   29.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771  -15.0000  -30.0000 120

 15 omega   87.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771 -125.0000  -60.0000 33

 16 omega   81.00  176.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771   45.0000  150.0000 95

 17 omega   39.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771 -125.0000   30.0000 26

 18 omega  118.00  152.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1771   30.0000  -90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0525039000
_diffrn_orient_matrix_UB_12      -0.1338924000
_diffrn_orient_matrix_UB_13      -0.0242645000
_diffrn_orient_matrix_UB_21      0.1409900000
_diffrn_orient_matrix_UB_22      0.0045906000
_diffrn_orient_matrix_UB_23      0.0143937000
_diffrn_orient_matrix_UB_31      -0.0477512000
_diffrn_orient_matrix_UB_32      -0.0702164000
_diffrn_orient_matrix_UB_33      0.0905422000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.1784
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.341
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1749
_refine_ls_R_factor_gt           0.0802
_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/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2579
_reflns_number_total             6186
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce02150j2.cif
_cod_data_source_block           20170516nami2
_cod_depositor_comments
'Adding full bibliography for 7229950--7229953.cif.'
_cod_database_code               7229952
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     CHNOS
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C31(H31), C32(H32),
  C33(H33), C34(H34)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N6(H6A,H6B), N8(H8A,H8B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'