Mechanochemical cocrystallization to improve the physicochemical properties of chlorzoxazone
Roy, Parag; Ghosh, Animesh; CrystEngComm  (2020) –; doi:10.1039/D0CE00635A

data_7240660
_publ_section_title
;
 Mechanochemical cocrystallization to improve the physicochemical
 properties of chlorzoxazone
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00635A
_journal_year                    2020
_chemical_formula_moiety         'C7 H4 Cl N O2, C6 H5 N O2'
_chemical_formula_sum            'C13 H9 Cl N2 O4'
_chemical_formula_weight         292.67
_chemical_name_systematic        CHZ_PA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-06 deposited with the CCDC.	2020-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                99.238(5)
_cell_angle_beta                 107.382(5)
_cell_angle_gamma                101.179(5)
_cell_formula_units_Z            2
_cell_length_a                   7.5903(4)
_cell_length_b                   9.0809(6)
_cell_length_c                   9.7444(5)
_cell_measurement_reflns_used    2639
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2310
_cell_measurement_theta_min      4.4350
_cell_volume                     611.46(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4324
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -12.00  79.00   1.00   12.57    --   10.22  57.00 -90.00   91
  2  \w    -59.00  35.00   1.00   12.57    --   10.22 -57.00 120.00   94
  3  \w    -67.00  15.00   1.00   12.57    --  -10.38 -57.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0519477000
_diffrn_orient_matrix_UB_12      -0.0028748000
_diffrn_orient_matrix_UB_13      -0.0745888000
_diffrn_orient_matrix_UB_21      -0.0203688000
_diffrn_orient_matrix_UB_22      0.0710818000
_diffrn_orient_matrix_UB_23      0.0228066000
_diffrn_orient_matrix_UB_31      0.0845666000
_diffrn_orient_matrix_UB_32      0.0405398000
_diffrn_orient_matrix_UB_33      -0.0083108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.445
_diffrn_reflns_theta_min         3.617
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_preparation       'LIQUID ASSISTED GRINDING WITH ACN'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0570P)^2^+0.1051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2464
_reflns_number_total             2843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00635a2.cif
_cod_data_source_block           chz_pa
_cod_original_cell_volume        611.46(6)
_cod_database_code               7240660
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H9 Cl N2 O4'
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H6), C10(H7), C3(H5), C5(H3), C12(H8), C6(H2), C4(H4), C13(H9)
;
_olex2_submission_original_sample_id CHZ_PA
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.796