#------------------------------------------------------------------------------
#$Date: 2022-03-25 09:49:32 +0200 (Fri, 25 Mar 2022) $
#$Revision: 273968 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104854.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8104854
loop_
_publ_author_name
'Averdunk, Arthur'
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of diphenyalmine hydrochloride antimony trichloride
 co-crystallizate, C12H12Cl4NSb -- Localization of hydrogen atoms
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              439
_journal_page_last               441
_journal_paper_doi               10.1515/ncrs-2020-0503
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C12 H12 N, 0.5(Cl8 Sb2)'
_chemical_formula_sum            'C12 H12 Cl4 N Sb'
_chemical_formula_weight         433.78
_chemical_name_systematic
'Diphenylammonium chloride antimony trichloride'
_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     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 100.3830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6693(2)
_cell_length_b                   20.2385(7)
_cell_length_c                   14.3908(5)
_cell_measurement_reflns_used    9396
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.47
_cell_volume                     1624.14(10)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15212
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.513
_exptl_absorpt_coefficient_mu    2.339
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8081
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]                                         
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0159P)²+0.8199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0430
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3408
_reflns_number_total             3736
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0503_suppl.cif
_cod_data_source_block           g
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104854
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.60254(2) 0.42241(2) 0.62212(2) 0.02581(5) Uani 1 1 d . . . . .
Cl1 Cl 0.74776(11) 0.43708(3) 0.78814(4) 0.04689(14) Uani 1 1 d . . . . .
Cl2 Cl 0.99203(9) 0.43626(3) 0.58696(4) 0.04769(14) Uani 1 1 d . . . . .
Cl3 Cl 0.63053(13) 0.30517(3) 0.62539(5) 0.06115(18) Uani 1 1 d . . . . .
Cl4 Cl 0.44458(8) 0.42553(2) 0.41040(3) 0.03228(10) Uani 1 1 d . . . . .
N1 N 0.9128(3) 0.37738(8) 0.34111(11) 0.0274(3) Uani 1 1 d . . . . .
H1 H 1.051(4) 0.3919(11) 0.3700(16) 0.036(6) Uiso 1 1 d . . . . .
H2 H 0.799(5) 0.3967(13) 0.3597(17) 0.046(7) Uiso 1 1 d . . . . .
C11 C 0.9006(3) 0.39522(9) 0.24101(13) 0.0299(4) Uani 1 1 d . . . . .
C12 C 1.0647(4) 0.36771(12) 0.19288(16) 0.0472(5) Uani 1 1 d . . . . .
H12 H 1.182142 0.337393 0.222883 0.057 Uiso 1 1 calc R U . . .
C13 C 1.0538(6) 0.38548(16) 0.09964(19) 0.0637(8) Uani 1 1 d . . . . .
H13 H 1.165023 0.367118 0.064711 0.076 Uiso 1 1 calc R U . . .
C14 C 0.8837(6) 0.42948(14) 0.05679(18) 0.0664(9) Uani 1 1 d . . . . .
H14 H 0.878347 0.441546 -0.007359 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7219(6) 0.45594(14) 0.10652(18) 0.0619(7) Uani 1 1 d . . . . .
H15 H 0.604324 0.486221 0.076552 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7285(5) 0.43894(11) 0.19990(16) 0.0445(5) Uani 1 1 d . . . . .
H16 H 0.616692 0.457088 0.234705 0.053 Uiso 1 1 calc R U . . .
C21 C 0.8949(3) 0.30587(9) 0.35992(14) 0.0302(4) Uani 1 1 d . . . . .
C22 C 0.7125(5) 0.27045(12) 0.3087(2) 0.0594(7) Uani 1 1 d . . . . .
H22 H 0.599787 0.291055 0.260593 0.071 Uiso 1 1 calc R U . . .
C23 C 0.6940(6) 0.20384(14) 0.3282(2) 0.0697(8) Uani 1 1 d . . . . .
H23 H 0.566367 0.178612 0.293553 0.084 Uiso 1 1 calc R U . . .
C24 C 0.8565(6) 0.17430(12) 0.3961(2) 0.0632(8) Uani 1 1 d . . . . .
H24 H 0.844960 0.128359 0.407992 0.076 Uiso 1 1 calc R U . . .
C25 C 1.0362(6) 0.21075(14) 0.4471(3) 0.0792(10) Uani 1 1 d . . . . .
H25 H 1.148017 0.190188 0.495546 0.095 Uiso 1 1 calc R U . . .
C26 C 1.0581(5) 0.27803(12) 0.4289(2) 0.0597(7) Uani 1 1 d . . . . .
H26 H 1.184133 0.303533 0.464108 0.072 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl2 Sb1 Cl3 93.49(2) . .
Cl2 Sb1 Cl1 91.85(2) . .
Cl3 Sb1 Cl1 95.39(2) . .
C11 N1 C21 115.19(15) . .
C11 N1 H1 105.4(15) . .
C21 N1 H1 109.2(15) . .
C11 N1 H2 107.1(17) . .
C21 N1 H2 108.3(17) . .
H1 N1 H2 112(2) . .
C16 C11 C12 122.6(2) . .
C16 C11 N1 118.98(18) . .
C12 C11 N1 118.45(18) . .
C11 C12 C13 118.0(2) . .
C11 C12 H12 121.0 . .
C13 C12 H12 121.0 . .
C14 C13 C12 120.7(3) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C15 C14 C13 120.0(2) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.5(3) . .
C14 C15 H15 119.7 . .
C16 C15 H15 119.7 . .
C11 C16 C15 118.3(2) . .
C11 C16 H16 120.9 . .
C15 C16 H16 120.9 . .
C26 C21 C22 122.1(2) . .
C26 C21 N1 118.80(19) . .
C22 C21 N1 119.12(18) . .
C21 C22 C23 118.8(2) . .
C21 C22 H22 120.6 . .
C23 C22 H22 120.6 . .
C24 C23 C22 120.6(3) . .
C24 C23 H23 119.7 . .
C22 C23 H23 119.7 . .
C23 C24 C25 119.7(2) . .
C23 C24 H24 120.1 . .
C25 C24 H24 120.1 . .
C24 C25 C26 120.7(3) . .
C24 C25 H25 119.6 . .
C26 C25 H25 119.6 . .
C21 C26 C25 118.1(3) . .
C21 C26 H26 120.9 . .
C25 C26 H26 120.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sb1 Cl2 2.3692(5) .
Sb1 Cl3 2.3781(6) .
Sb1 Cl1 2.4010(5) .
N1 C11 1.475(2) .
N1 C21 1.479(2) .
N1 H1 0.87(2) .
N1 H2 0.84(3) .
C11 C16 1.370(3) .
C11 C12 1.374(3) .
C12 C13 1.380(3) .
C12 H12 0.9500 .
C13 C14 1.374(4) .
C13 H13 0.9500 .
C14 C15 1.370(4) .
C14 H14 0.9500 .
C15 C16 1.381(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C26 1.352(3) .
C21 C22 1.361(3) .
C22 C23 1.385(4) .
C22 H22 0.9500 .
C23 C24 1.355(4) .
C23 H23 0.9500 .
C24 C25 1.361(4) .
C24 H24 0.9500 .
C25 C26 1.396(4) .
C25 H25 0.9500 .
C26 H26 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl4 0.87(2) 2.31(2) 3.1545(17) 165(2) 1_655
N1 H2 Cl4 0.84(3) 2.33(3) 3.1533(17) 167(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C21 N1 C11 C16 123.6(2) . . . .
C21 N1 C11 C12 -57.1(2) . . . .
C16 C11 C12 C13 0.2(3) . . . .
N1 C11 C12 C13 -179.1(2) . . . .
C11 C12 C13 C14 0.1(4) . . . .
C12 C13 C14 C15 -0.3(4) . . . .
C13 C14 C15 C16 0.2(4) . . . .
C12 C11 C16 C15 -0.3(3) . . . .
N1 C11 C16 C15 179.0(2) . . . .
C14 C15 C16 C11 0.1(4) . . . .
C11 N1 C21 C26 131.0(2) . . . .
C11 N1 C21 C22 -50.4(3) . . . .
C26 C21 C22 C23 0.0(4) . . . .
N1 C21 C22 C23 -178.6(2) . . . .
C21 C22 C23 C24 -0.8(5) . . . .
C22 C23 C24 C25 1.5(5) . . . .
C23 C24 C25 C26 -1.3(5) . . . .
C22 C21 C26 C25 0.2(4) . . . .
N1 C21 C26 C25 178.8(3) . . . .
C24 C25 C26 C21 0.5(5) . . . .
