Multicomponent crystals of clotrimazole: a combined theoretical and experimental study
Li, Chang; Wu, Di; Li, Jiulong; Ji, Xu; Qi, Luguang; Sun, Qin; Wang, Aiyu; Xie, Chuang; Gong, Junbo; Chen, Wei; CrystEngComm 23 (2021) 6977–6993; doi:10.1039/D1CE00934F

data_7243474
_publ_section_title
;
 Multicomponent crystals of clotrimazole: a combined theoretical and
 experimental study
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6977
_journal_page_last               6993
_journal_paper_doi               10.1039/D1CE00934F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 Cl N2, C7 H5 O4'
_chemical_formula_sum            'C29 H23 Cl N2 O4'
_chemical_formula_weight         498.94
_chemical_name_common            'Clotrimazole 2,3-dihydroxybenzoate'
_chemical_name_systematic
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 2,3-dihydroxybenzoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-25 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0772(7)
_cell_length_b                   8.2738(3)
_cell_length_c                   13.8978(5)
_cell_measurement_reflns_used    14048
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6680
_cell_measurement_theta_min      2.4000
_cell_volume                     2423.62(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_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   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312610000
_diffrn_orient_matrix_UB_12      -0.0034430000
_diffrn_orient_matrix_UB_13      -0.0188194000
_diffrn_orient_matrix_UB_21      0.0004707000
_diffrn_orient_matrix_UB_22      -0.0848087000
_diffrn_orient_matrix_UB_23      0.0073010000
_diffrn_orient_matrix_UB_31      -0.0124696000
_diffrn_orient_matrix_UB_32      -0.0116942000
_diffrn_orient_matrix_UB_33      -0.0468966000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29389
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.858
_diffrn_reflns_theta_min         1.932
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       rod
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         8262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0507
_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^)+(0.0518P)^2^+0.0633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                6862
_reflns_number_total             8262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00934f2.cif
_cod_data_source_block           r20210116d
_cod_depositor_comments
'Adding full bibliography for 7243468--7243476.cif.'
_cod_database_code               7243474
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C10(H10), C9(H9), C2(H2A), C4(H4), C28(H28), C3(H3), C22(H22),
  C19(H19), C25(H25), C23(H23), C13(H13), C14(H14), C17(H17), C21(H21),
 C15(H15), C20(H20), C26(H26), C27(H27), C16(H16)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1A)
;
_shelx_res_checksum              11632
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.778