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_7243470
_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, C12 H7 O4, C2 H6 O'
_chemical_formula_sum            'C36 H31 Cl N2 O5'
_chemical_formula_weight         607.08
_chemical_name_common            'Clotrimazole 4-Carboxy-1-naphthoate'
_chemical_name_systematic
'1-((2-chlorophenyl)(diphenyl)methyl)-1H-imidazol-3-ium 4-Carboxy-1-naphthoate'
_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             2021-05-24
_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                78.390(4)
_cell_angle_beta                 71.852(4)
_cell_angle_gamma                89.207(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4734(4)
_cell_length_b                   12.1901(6)
_cell_length_c                   13.6109(7)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4890
_cell_measurement_theta_min      1.7490
_cell_volume                     1461.05(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.708
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88204
_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            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       rod
_exptl_crystal_F_000             636
_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         1.603
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.023(3)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         5172
_refine_ls_number_restraints     83
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0965P)^2^+1.9895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4268
_reflns_number_total             5172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00934f2.cif
_cod_data_source_block           r20210126c
_cod_depositor_comments
'Adding full bibliography for 7243468--7243476.cif.'
_cod_database_code               7243470
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-C37
 1.45 with sigma of 0.02
 C37-C38
 1.54 with sigma of 0.02
 C35-C36
 1.52 with sigma of 0.02
 O6-C35
 1.45 with sigma of 0.02
 C35-C35_$1
 3.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C24: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O5 \\sim C37 \\sim C38: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.001 within 2A
O6 \\sim C35 \\sim O5 \\sim C37 \\sim C36 \\sim C38: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.001 within 2A
4. Rigid body (RIGU) restrains
 O5, C37, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O5, O6, C35, C37, C38, C36
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O6)=Sof(H6)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 Sof(H36C)=1-FVAR(1)
 Sof(O5)=Sof(H5)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C37)=Sof(H37A)=
 Sof(H37B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C35(H35A,H35B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C11(H11), C8(H8), C18(H18), C10(H10), C15(H15), C9(H9),
 C22(H22), C4(H4A), C14(H14), C31(H31), C28(H28), C3(H3), C34(H34), C19(H19),
 C27(H27), C26(H26), C20(H20), C21(H21), C32(H32), C24(H24), C33(H33)
6.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C)
6.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O6(H6)
;
_shelx_res_checksum              80987
_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
;