Structural variety of clofaziminium salts: effect of the counter-ion on clofaziminium conformation and crystal packing
Bodart, Laurie; Tumanov, Nikolay; Wouters, Johan; Acta Crystallographica Section B 75 (2019) –; doi:10.1107/S2052520619007649

data_2108447
_publ_section_title
;
 Structural variety of clofaziminium salts: effect of the counter-ion on
 clofaziminium conformation and crystal packing
;
_journal_coeditor_code           AW5025
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520619007649
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety
;
C27 H23 Cl2 N4 + , 0.5C8 H4 O4 2- , 0.5C8 H6 O4 
;
_chemical_formula_sum            'C35 H28 Cl2 N4 O4'
_chemical_formula_weight         639.51
_chemical_name_common
;
bis-clofaziminium terephthalate terephthalic acid
;
_chemical_name_systematic
;
N-[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]
-2,10-dihydrophenazin-2-ylidene]propan-2-aminium 
benzene-1,4-dicarboxylic acid benzene-1,4-dicarboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                71.183(3)
_cell_angle_beta                 73.984(3)
_cell_angle_gamma                76.148(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4028(3)
_cell_length_b                   10.8454(3)
_cell_length_c                   15.4229(5)
_cell_measurement_reflns_used    5839
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.3580
_cell_measurement_theta_min      2.4810
_cell_volume                     1561.33(9)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur Ruby Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0255
_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       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13059
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.475
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'Metallic dark red'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       Prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.717
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.413
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0540P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4554
_reflns_number_total             5704
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            aw5025sup1.cif
_cod_data_source_block           lb0329_CLZ-TRPTA_reMo
_cod_database_code               2108447
_cod_database_fobs_code          2108447
_shelx_shelxl_version_number     2016/6
_oxdiff_exptl_absorpt_empirical_full_min 0.869
_oxdiff_exptl_absorpt_empirical_full_max 1.156
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              38194
_shelx_hkl_checksum              22498