The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions
Kaur, Manpreet; Jasinski, Jerry P.; Yathirajan, Hemmige S.; Kavitha, Channappa N.; Glidewell, Christopher; Acta Crystallographica Section E 71 (2015) 406–413; doi:10.1107/S205698901500554X

data_2240528
_publ_section_title
;
 The crystal structures of three clozapinium salts: different molecular
 configurations, and supramolecular assembly in one, two and three
 dimensions
;
_journal_coeditor_code           HB7383
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              406
_journal_page_last               413
_journal_paper_doi               10.1107/S205698901500554X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C18 H20 Cl N4 +, C7 H5 O3 -'
_chemical_formula_moiety         'C18 H20 Cl N4 +, C7 H5 O3 -'
_chemical_formula_sum            'C25 H25 Cl N4 O3'
_chemical_formula_weight         464.94
_chemical_name_systematic
;
Clozapinium 2-hydroxybenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.325(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4296(5)
_cell_length_b                   15.3728(5)
_cell_length_c                   8.6359(3)
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.602
_cell_measurement_theta_min      3.834
_cell_volume                     2313.88(13)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlisRed (Agilent, 2012)
;
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Agilent Eos Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7244
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.602
_diffrn_reflns_theta_min         3.834
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  0.705
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.362
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1674 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.022(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0563
_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^)+(0.1069P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                3962
_reflns_number_total             4069
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb7383sup1.cif
_cod_data_source_block           III
_cod_database_code               2240528
_cod_database_fobs_code          2240528
_shelx_estimated_absorpt_t_min   0.527
_shelx_estimated_absorpt_t_max   0.721
_shelx_hkl_checksum              97891
_shelx_res_checksum              44527
_shelxl_version_number           2.014