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_7243475
_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, C10 H5 O8'
_chemical_formula_sum            'C32 H23 Cl N2 O8'
_chemical_formula_weight         598.97
_chemical_name_common            'Clotrimazolium  Pyromellitate'
_chemical_name_systematic
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium trihydrogen 1,2,4,5-Benzenetetracarboxylate'
_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
_audit_creation_date             2021-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-08 deposited with the CCDC.	2021-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                69.389(4)
_cell_angle_beta                 89.642(4)
_cell_angle_gamma                89.690(4)
_cell_formula_units_Z            4
_cell_length_a                   11.7142(6)
_cell_length_b                   15.5030(7)
_cell_length_c                   16.6489(8)
_cell_measurement_reflns_used    12374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6280
_cell_measurement_theta_min      1.8370
_cell_volume                     2829.9(2)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    2.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    2.00    --  -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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.545
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20351
_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    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.492
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     788
_refine_ls_number_reflns         15773
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.1045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.2005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8931
_reflns_number_total             15773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00934f2.cif
_cod_data_source_block           r20210116b
_cod_depositor_comments
'Adding full bibliography for 7243468--7243476.cif.'
_cod_database_code               7243475
_shelx_shelxl_version_number     2018/3
_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. Restrained distances
 H6-O6 = H14-O14
 0.82 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C7(H7), C35(H35), C13(H13), C4(H4), C43(H43), C38(H38),
 C44(H44), C45(H45), C12(H12), C22(H22), C11(H11), C52(H52), C16(H16), C48(H48),
  C20(H20), C17(H17), C18(H18), C32(H32), C64(H64), C19(H19), C23(H23),
 C26(H26), C51(H51), C24(H24), C50(H50), C49(H49), C58(H58), C61(H61), C62(H62),
  C31(H31), C25(H25), C29(H29), C63(H63), C54(H54), C30(H30), C57(H57),
 C55(H55), C56(H56)
3.b Idealised tetrahedral OH refined as rotating group:
 O9(H9), O12(H12A), O1(H1A), O4(H4A)
;
_shelx_res_checksum              36992
_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
;