Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt containing a very short O—H···O hydrogen bond with chlorprothixene
Shaibah, Mohammed A. E.; Yathirajan, Hemmige S.; Rathore, Ravindranath S.; Furuya, Tetsundo; Haraguchi, Tomoyuki; Akitsu, Takashiro; Glidewell, Christopher; Acta Crystallographica Section E 75 (2019) 292–298; doi:10.1107/S2056989019001385

data_2242838
_publ_section_title
;
 Co-crystallization of 3,5-dinitrobenzoic acid with two antipsychotic
 agents: a simple 1:1 salt with trihexyphenidyl and a 1:2 acid salt
 containing a very short O---H&#x00B7;&#x00B7;&#x00B7;O hydrogen bond with
 chlorprothixene
;
_journal_coeditor_code           ZL2748
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              292
_journal_page_last               298
_journal_paper_doi               10.1107/S2056989019001385
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H19 Cl N S +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_moiety         'C18 H19 Cl N S +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_sum            'C32 H26 Cl N5 O12 S'
_chemical_formula_weight         740.09
_chemical_name_common
;
[3-(2-Chloro-9<i>H</i>-thioxanthen-9-yl)propyl]dimethylammonium
hydrogen bis(3,5-dinitrobenzoate)
;
_chemical_name_systematic
'(<i>Z</i>)-3-(2-Chloro-9<i>H</i>-thioxanthen-9-yl)-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium hydrogen bis(3,5-dinitrobenzoate)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.6910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3454(8)
_cell_length_b                   24.3857(16)
_cell_length_c                   11.6098(8)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.421
_cell_measurement_theta_min      1.799
_cell_volume                     3205.4(4)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17539
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_min         1.799
_diffrn_source                   'fine focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.295
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         7139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0482P)^2^+1.3713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                6365
_reflns_number_total             7139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2748sup1.cif
_cod_data_source_block           II
_cod_database_code               2242838
_cod_database_fobs_code          2242838
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.927
_shelx_hkl_checksum              62005
_shelx_res_checksum              64348
_shelxl_version_number           2.014