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_2242837
_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          'C20 H32 N O +, C7 H3 N2 O6 -'
_chemical_formula_moiety         'C20 H32 N O +, C7 H3 N2 O6 -'
_chemical_formula_sum            'C27 H35 N3 O7'
_chemical_formula_weight         513.58
_chemical_name_common
;
Trihexyphenidylium 3,5-dinitrobenzoate
;
_chemical_name_systematic
;
1-(3-Cyclohexyl-3-hydroxy-3-phenylpropyl)piperidin-1-ium 3,5-dinitrobenzoate
;
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                111.9230(10)
_cell_angle_beta                 114.3250(10)
_cell_angle_gamma                95.9030(10)
_cell_formula_units_Z            2
_cell_length_a                   11.2743(12)
_cell_length_b                   11.2898(12)
_cell_length_c                   12.6478(13)
_cell_measurement_reflns_used    5525
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.516
_cell_measurement_theta_min      1.989
_cell_volume                     1296.6(2)
_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 0.976
_diffrn_measured_fraction_theta_max 0.927
_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  0.0134
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7191
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         1.989
_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    0.095
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.613
_exptl_crystal_size_mid          0.577
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0513P)^2^+0.3666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                4819
_reflns_number_total             5525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2748sup1.cif
_cod_data_source_block           I
_cod_database_code               2242837
_cod_database_fobs_code          2242837
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              79221
_shelx_res_checksum              32166
_shelxl_version_number           2.014