A very short O—H···O hydrogen bond in the structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)
Shaibah, Mohammed A. E.; Kavitha, Channappa N.; Yathirajan, Hemmige S.; Foro, Sabine; Glidewell, Christopher; Acta Crystallographica Section E 76 (2020) 1629–1633; doi:10.1107/S2056989020012268

data_2243594
_publ_section_title
;
 A very short O---H&#x00B7;&#x00B7;&#x00B7;O hydrogen bond in the
 structure of clozapinium hydrogen bis(3,5-dinitrobenzoate)
;
_journal_coeditor_code           HB7944
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1629
_journal_page_last               1633
_journal_paper_doi               10.1107/S2056989020012268
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H20 Cl N4 +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_moiety         'C18 H20 Cl N4 +, C7 H3 N2 O6 -, C7 H4 N2 O6'
_chemical_formula_sum            'C32 H27 Cl N8 O12'
_chemical_formula_weight         751.07
_chemical_name_common
;
Clozapinium hydrogen bis(3,5-dinitrobenzoate)
;
_chemical_name_systematic
;4-[6-Chloro-2,9-diazatricyclo[9.4.0.0^3,8^]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl]-1-methylpiperazin-1-ium
3,5-dinitrobenzoate--3,5-dinitrobenzic acid (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 98.478(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4102(6)
_cell_length_b                   24.629(2)
_cell_length_c                   18.4460(10)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.885
_cell_measurement_theta_min      2.838
_cell_volume                     3329.7(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur Sapphire CCD detector
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13700
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.546
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0620
_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^)+(0.0452P)^2^+1.0626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                3811
_reflns_number_total             6870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7944sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243594
_cod_database_fobs_code          2243594
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.962
_shelx_hkl_checksum              34851
_shelx_res_checksum              64449
_shelxl_version_number           2.014