4-(4-Chlorophenyl)-1-[3-(4-fluorobenzoyl)propyl]-4-hydroxypiperidin-1-ium 2,4,6-trinitrophenolate (haloperidol picrate)
Jasinski, Jerry P.; Butcher, Ray J.; Hakim Al-Arique, Q. N. M.; Yathirajan, H. S.; Narayana, B.; Acta Crystallographica Section E 65 (2009) o2403–o2404; doi:10.1107/S1600536809033261

data_2223437
_publ_section_title
;
 4-(4-Chlorophenyl)-1-[3-(4-fluorobenzoyl)propyl]-4-hydroxypiperidin-1-ium
 2,4,6-trinitrophenolate (haloperidol picrate)
;
_journal_coeditor_code           IM2134
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2403
_journal_page_last               o2404
_journal_paper_doi               10.1107/S1600536809033261
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H24 Cl F N O2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C21 H24 Cl F N O2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C27 H26 Cl F N4 O9'
_chemical_formula_weight         604.97
_chemical_name_common            'haloperidol picrate'
_chemical_name_systematic
;
4-(4-Chlorophenyl)-1-[3-(4-fluorobenzoyl)propyl]-4-hydroxypiperidin-1-ium
2,4,6-trinitrophenolate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9089(5)
_cell_length_b                   12.5934(3)
_cell_length_c                   14.5074(5)
_cell_measurement_reflns_used    8346
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      32.6425
_cell_measurement_theta_min      4.9617
_cell_volume                     2723.82(15)
_computing_cell_refinement
'<i>CrysAlis RED</i> (Oxford Diffraction, 2007)'
_computing_data_collection
'<i>CrysAlis Pro</i> (Oxford Diffraction, 2007)'
_computing_data_reduction
'<i>CrysAlis RED</i> (Oxford Diffraction, 2007)'
_computing_molecular_graphics    '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material  '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_structure_refinement  '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type
;
Oxford Diffraction Gemini R CCD
;
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19020
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.72
_diffrn_reflns_theta_min         5.03
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.241
_refine_ls_abs_structure_details 'Flack (1983), 2287 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         7472
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                5784
_reflns_number_total             7472
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            im2134.cif
_cod_data_source_block           I
_cod_original_cell_volume        2723.8(2)
_cod_database_code               2223437
_cod_database_fobs_code          2223437