Synthesis and structure of clozapine <i>N</i>-oxide hemi(hydrochloride): an infinite hydrogen-bonded poly[<i>n</i>]catenane
van der Peet, Phillip L.; Joyce, Rohan D.; Ott, Holger; Marcuccio, Sebastian M.; White, Jonathan M.; Williams, Spencer J.; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989022009306

data_2244183
_publ_section_title
;
 Synthesis and structure of clozapine <i>N</i>-oxide hemi(hydrochloride):
 an infinite hydrogen-bonded poly[<i>n</i>]catenane
;
_journal_coeditor_code           HB8039
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022009306
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          '2C18 H19 Cl1 N4 O1, H Cl'
_chemical_formula_moiety         '2(C18 H19 Cl1 N4 O1), H Cl'
_chemical_formula_sum            'C36 H39 Cl3 N8 O2'
_chemical_formula_weight         722.10
_chemical_name_common
;
Clozapine <i>N</i>-oxide hemi(hydrochloride)
;
_chemical_name_systematic
;8-Chloro-11-(4-methyl-1-piperazinyl)-5<i>H</i>-dibenzo[<i>b</i>,<i>e</i>][1,4]diazepine <i>N</i>-oxide
hemi(hydrochloride)
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           87
_space_group_name_Hall           '-I 4'
_space_group_name_H-M_alt        'I 4/m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.305(2)
_cell_length_b                   17.305(2)
_cell_length_c                   26.040(5)
_cell_measurement_reflns_used    5908
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      1.4
_cell_volume                     7798(2)
_computing_cell_refinement
;
<i>XDS</i> (Kabsch, 1993)
;
_computing_data_collection       'AS QEGUI'
_computing_data_reduction
;
<i>XDS</i> (Kabsch, 1993)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
WINGX (Farrugia, 2012)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.710757
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            66433
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.773
_diffrn_reflns_theta_min         1.413
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.491
_refine_ls_extinction_coef       0.0069(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016/6 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0661P)^2^+11.4576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                5096
_reflns_number_total             5901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8039sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        7798(3)
_cod_database_code               2244183
_shelx_hkl_checksum              52636
_shelx_res_checksum              99554
_shelx_fab_checksum              16807
_cod_database_fobs_code 2244183