Taking advantage of solvate formation to modulate drug–drug ratio in clofaziminium diclofenac salts
Bodart, Laurie; Prinzo, Maria; Derlet, Amélie; Tumanov, Nikolay; Wouters, Johan; CrystEngComm 23 (2021) 185–201; doi:10.1039/D0CE01400A

data_7241524
_publ_section_title
;
 Taking advantage of solvate formation to modulate drug--drug ratio in
 clofaziminium diclofenac salts
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              185
_journal_page_last               201
_journal_paper_doi               10.1039/D0CE01400A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety
;	
C27 H23 Cl2 N4, C14 H10 Cl2 N O2, C14 H11 Cl2 N O2, 
2(C2 H3 N)
;
_chemical_formula_sum            'C59 H50 Cl6 N8 O4'
_chemical_formula_weight         1147.77
_chemical_name_common
;
Clofaziminium 1+ diclofenac 1- 
diclofenac acetonitrile solvated
cocrystal of salt
;
_chemical_name_systematic
;
2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid 
N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-
2,10-dihydrophenazin-2-ylidene]propan-2-aminium 
bis(acetonitrile) 
2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate
;
_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
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-09-17 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                74.882(7)
_cell_angle_beta                 61.685(8)
_cell_angle_gamma                64.227(7)
_cell_formula_units_Z            2
_cell_length_a                   15.0694(11)
_cell_length_b                   15.2735(10)
_cell_length_c                   15.5991(13)
_cell_measurement_reflns_used    10211
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.9030
_cell_measurement_theta_min      3.2090
_cell_volume                     2839.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27894
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.276
_diffrn_reflns_theta_max         67.276
_diffrn_reflns_theta_min         3.221
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.196
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00129(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     744
_refine_ls_number_reflns         10010
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0839P)^2^+0.4564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7543
_reflns_number_total             10010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01400a2.cif
_cod_data_source_block           lb0721_CFZ-DCF_1-2_in_MeCN
_cod_depositor_comments
'Adding full bibliography for 7241513--7241524.cif.'
_cod_database_code               7241524
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.437
_shelx_estimated_absorpt_t_max   0.663
_oxdiff_exptl_absorpt_empirical_full_min 0.721
_oxdiff_exptl_absorpt_empirical_full_max 4.849
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              804