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_7243472
_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 H17 Cl N2, C9 H7 N O2'
_chemical_formula_sum            'C31 H24 Cl N3 O2'
_chemical_formula_weight         505.98
_chemical_name_common            'Clotrimazole Indole-6-carboxylic acid'
_chemical_name_systematic
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazole Indole-6-carboxylic acid'
_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             2021-03-21
_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                95.603(4)
_cell_angle_beta                 95.284(4)
_cell_angle_gamma                97.549(4)
_cell_formula_units_Z            2
_cell_length_a                   8.6793(3)
_cell_length_b                   10.6795(6)
_cell_length_c                   13.6524(7)
_cell_measurement_reflns_used    9586
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6960
_cell_measurement_theta_min      1.9760
_cell_volume                     1241.41(11)
_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 0.897
_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  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_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      -0.0068366000
_diffrn_orient_matrix_UB_12      0.0657032000
_diffrn_orient_matrix_UB_13      0.0034159000
_diffrn_orient_matrix_UB_21      0.0179271000
_diffrn_orient_matrix_UB_22      0.0017458000
_diffrn_orient_matrix_UB_23      -0.0495417000
_diffrn_orient_matrix_UB_31      -0.0806570000
_diffrn_orient_matrix_UB_32      -0.0149970000
_diffrn_orient_matrix_UB_33      -0.0170396000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18814
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.905
_diffrn_reflns_theta_min         1.936
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95470
_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    1.354
_exptl_crystal_description       rod
_exptl_crystal_F_000             528
_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         0.349
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         8339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0589P)^2^+0.2584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6173
_reflns_number_total             8339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00934f2.cif
_cod_data_source_block           r20201209b
_cod_depositor_comments
'Adding full bibliography for 7243468--7243476.cif.'
_cod_original_cell_volume        1241.41(10)
_cod_database_code               7243472
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C21(H21), C19(H19), C12(H12), C23(H23), C10(H10),
 C25(H25), C18(H18), C22(H22), C24(H24), C16(H16), C3(H3A), C17(H17), C4(H4),
 C7(H7), C9(H9), C31(H31), C6(H6), C28(H28), C30(H30), C29(H29)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              1791
_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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.633