#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:07:02 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/92/4349244.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_4349244
loop_
_publ_author_name
'Arlt, Sören'
'Harloff, Jörg'
'Schulz, Axel'
'Stoffers, Alrik'
'Villinger, Alexander'
_publ_section_title
;
 Cyanido Antimonate(III) and Bismuthate(III) Anions.
;
_journal_issue                   23
_journal_name_full               'Inorganic chemistry'
_journal_page_first              12321
_journal_page_last               12328
_journal_paper_doi               10.1021/acs.inorgchem.6b02174
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C36 H30 N P2 +, C N -, C7 H8'
_chemical_formula_sum            'C44 H38 N2 P2'
_chemical_formula_weight         656.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.391(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6941(6)
_cell_length_b                   10.7497(4)
_cell_length_c                   22.1216(8)
_cell_measurement_reflns_used    9210
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.29
_cell_measurement_theta_min      2.35
_cell_volume                     3472.5(2)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            31416
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.499
_diffrn_reflns_theta_min         2.353
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6289
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0412
_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/[σ²(Fo²)+(0.0565P)²+1.6148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5138
_reflns_number_total             6289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b02174_si_002.cif
_cod_data_source_block           is_as472_PPN_CN_Toluene
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4349244
_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.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1A C 0.4975(10) 0.939(2) 0.2361(7) 0.047(3) Uani 0.342(15) 1 d D U P A 1
N1A N 0.5171(9) 0.9338(15) 0.2814(5) 0.048(2) Uani 0.342(15) 1 d D U P A 1
C1B C 0.5023(16) 0.957(2) 0.2901(12) 0.043(2) Uani 0.158(15) 1 d D U P A 2
N1B N 0.5000 0.9132(19) 0.2500 0.045(3) Uani 0.32(3) 2 d DS TU P A 2
N2 N 0.0000 0.97088(10) 0.2500 0.0156(2) Uani 1 2 d S T P . .
P1 P 0.03410(2) 0.90947(2) 0.31418(2) 0.01424(7) Uani 1 1 d . . . . .
C2 C 0.05661(7) 1.03379(10) 0.36781(5) 0.0206(2) Uani 1 1 d . . . . .
C3 C 0.08202(9) 1.00378(14) 0.42898(5) 0.0317(3) Uani 1 1 d . . . . .
H3 H 0.0911 0.9195 0.4411 0.038 Uiso 1 1 calc R U . . .
C4 C 0.09375(11) 1.09865(17) 0.47172(6) 0.0442(4) Uani 1 1 d . . . . .
H4 H 0.1111 1.0793 0.5133 0.053 Uiso 1 1 calc R U . . .
C5 C 0.08026(10) 1.22133(16) 0.45392(7) 0.0445(4) Uani 1 1 d . . . . .
H5 H 0.0880 1.2855 0.4836 0.053 Uiso 1 1 calc R U . . .
C6 C 0.05578(8) 1.25154(13) 0.39369(7) 0.0366(3) Uani 1 1 d . . . . .
H6 H 0.0470 1.3361 0.3819 0.044 Uiso 1 1 calc R U . . .
C7 C 0.04406(7) 1.15725(11) 0.35021(6) 0.0246(2) Uani 1 1 d . . . . .
H7 H 0.0275 1.1774 0.3086 0.029 Uiso 1 1 calc R U . . .
C8 C 0.13656(6) 0.82032(9) 0.31173(4) 0.01692(17) Uani 1 1 d . . . . .
C9 C 0.22105(7) 0.88082(10) 0.32114(5) 0.0216(2) Uani 1 1 d . . . . .
H9 H 0.2243 0.9635 0.3364 0.026 Uiso 1 1 calc R U . . .
C10 C 0.30039(7) 0.82063(12) 0.30825(6) 0.0274(2) Uani 1 1 d . . . . .
H10 H 0.3578 0.8621 0.3144 0.033 Uiso 1 1 calc R U . . .
C11 C 0.29522(8) 0.69974(12) 0.28641(6) 0.0286(2) Uani 1 1 d . . . . .
H11 H 0.3492 0.6588 0.2771 0.034 Uiso 1 1 calc R U . . .
C12 C 0.21189(8) 0.63792(11) 0.27808(5) 0.0254(2) Uani 1 1 d . . . . .
H12 H 0.2094 0.5542 0.2642 0.030 Uiso 1 1 calc R U . . .
C13 C 0.13215(7) 0.69807(10) 0.28996(5) 0.02000(19) Uani 1 1 d . . . . .
H13 H 0.0749 0.6564 0.2833 0.024 Uiso 1 1 calc R U . . .
C14 C -0.05292(7) 0.81718(9) 0.34416(4) 0.01723(18) Uani 1 1 d . . . . .
C15 C -0.03756(8) 0.70178(10) 0.37177(5) 0.0238(2) Uani 1 1 d . . . . .
H15 H 0.0219 0.6660 0.3757 0.029 Uiso 1 1 calc R U . . .
C16 C -0.11022(9) 0.63899(11) 0.39374(6) 0.0292(2) Uani 1 1 d . . . . .
H16 H -0.1002 0.5594 0.4119 0.035 Uiso 1 1 calc R U . . .
C17 C -0.19650(8) 0.69142(12) 0.38931(5) 0.0292(2) Uani 1 1 d . . . . .
H17 H -0.2453 0.6483 0.4049 0.035 Uiso 1 1 calc R U . . .
C18 C -0.21208(8) 0.80680(12) 0.36216(5) 0.0272(2) Uani 1 1 d . . . . .
H18 H -0.2715 0.8428 0.3591 0.033 Uiso 1 1 calc R U . . .
C19 C -0.14067(7) 0.86942(11) 0.33956(5) 0.0221(2) Uani 1 1 d . . . . .
H19 H -0.1514 0.9484 0.3208 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2892(2) 0.83206(18) 0.51689(12) 0.0454(9) Uani 0.5 1 d G . P . .
C21 C 0.3225(2) 0.7646(3) 0.47048(12) 0.0467(11) Uani 0.5 1 d G . P . .
H21 H 0.3756 0.7924 0.4535 0.056 Uiso 0.5 1 calc R U P . .
C22 C 0.2782(3) 0.6566(2) 0.44885(15) 0.0757(19) Uani 0.5 1 d G . P . .
H22 H 0.3010 0.6105 0.4171 0.091 Uiso 0.5 1 calc R U P . .
C23 C 0.2006(3) 0.61598(19) 0.4736(2) 0.0702(16) Uani 0.5 1 d G . P . .
H23 H 0.1703 0.5421 0.4589 0.084 Uiso 0.5 1 calc R U P . .
C24 C 0.1672(3) 0.6834(3) 0.5201(2) 0.0742(19) Uani 0.5 1 d G . P . .
H24 H 0.1142 0.6557 0.5370 0.089 Uiso 0.5 1 calc R U P . .
C25 C 0.2115(3) 0.7915(2) 0.54168(15) 0.0660(19) Uani 0.5 1 d G . P . .
H25 H 0.1887 0.8376 0.5734 0.079 Uiso 0.5 1 calc R U P . .
C26 C 0.3340(4) 0.9505(4) 0.53924(19) 0.0661(12) Uani 0.5 1 d . . P . .
H26A H 0.3956 0.9551 0.5263 0.099 Uiso 0.5 1 calc R U P . .
H26B H 0.3384 0.9530 0.5838 0.099 Uiso 0.5 1 calc R U P . .
H26C H 0.2976 1.0213 0.5224 0.099 Uiso 0.5 1 calc R U P . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
N1A C1A C1A 155(6) 2_655 2_655
N1A C1A N1A 162(6) 2_655 .
C1A C1A N1A 10(2) 2_655 .
C1A N1A C1A 15(4) 2_655 .
C1A N1A N1A 13(4) 2_655 2_655
C1A N1A N1A 5.3(17) . 2_655
N1B C1B C1B 28(3) . 2_655
C1B N1B C1B 123(5) . 2_655
P1 N2 P1 131.10(8) . 2
N2 P1 C8 112.12(4) . .
N2 P1 C2 107.28(5) . .
C8 P1 C2 108.97(5) . .
N2 P1 C14 112.95(4) . .
C8 P1 C14 110.48(5) . .
C2 P1 C14 104.64(5) . .
C7 C2 C3 120.23(10) . .
C7 C2 P1 121.15(8) . .
C3 C2 P1 118.51(9) . .
C4 C3 C2 119.23(14) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C5 C4 C3 120.20(14) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C6 C5 C4 120.84(12) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 119.60(14) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C2 C7 C6 119.89(12) . .
C2 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C9 C8 C13 119.68(9) . .
C9 C8 P1 118.87(8) . .
C13 C8 P1 120.43(7) . .
C10 C9 C8 120.30(10) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 119.57(11) . .
C11 C10 H10 120.2 . .
C9 C10 H10 120.2 . .
C10 C11 C12 120.59(11) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C12 C13 120.17(11) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C13 C8 119.67(10) . .
C12 C13 H13 120.2 . .
C8 C13 H13 120.2 . .
C15 C14 C19 119.56(9) . .
C15 C14 P1 124.45(8) . .
C19 C14 P1 115.97(8) . .
C14 C15 C16 119.44(11) . .
C14 C15 H15 120.3 . .
C16 C15 H15 120.3 . .
C17 C16 C15 120.65(11) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C16 C17 C18 120.14(10) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C19 119.72(11) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C18 C19 C14 120.47(11) . .
C18 C19 H19 119.8 . .
C14 C19 H19 119.8 . .
C21 C20 C25 120.0 . .
C21 C20 C26 120.7(3) . .
C25 C20 C26 119.3(3) . .
C22 C21 C20 120.0 . .
C22 C21 H21 120.0 . .
C20 C21 H21 120.0 . .
C21 C22 C23 120.0 . .
C21 C22 H22 120.0 . .
C23 C22 H22 120.0 . .
C22 C23 C24 120.0 . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C25 C24 C23 120.0 . .
C25 C24 H24 120.0 . .
C23 C24 H24 120.0 . .
C24 C25 C20 120.0 . .
C24 C25 H25 120.0 . .
C20 C25 H25 120.0 . .
C20 C26 H26A 109.5 . .
C20 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C20 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1A N1A 0.43(2) 2_655
C1A C1A 0.61(3) 2_655
C1A N1A 1.014(11) .
N1A C1A 0.43(2) 2_655
N1A N1A 1.42(2) 2_655
C1B N1B 1.005(12) .
C1B C1B 1.77(5) 2_655
N1B C1B 1.005(12) 2_655
N2 P1 1.5950(5) .
N2 P1 1.5951(5) 2
P1 C8 1.7905(10) .
P1 C2 1.7932(10) .
P1 C14 1.8023(10) .
C2 C7 1.3897(16) .
C2 C3 1.4006(16) .
C3 C4 1.3884(18) .
C3 H3 0.9500 .
C4 C5 1.384(3) .
C4 H4 0.9500 .
C5 C6 1.380(2) .
C5 H5 0.9500 .
C6 C7 1.3949(15) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.3965(14) .
C8 C13 1.3986(14) .
C9 C10 1.3904(15) .
C9 H9 0.9500 .
C10 C11 1.3856(18) .
C10 H10 0.9500 .
C11 C12 1.3874(17) .
C11 H11 0.9500 .
C12 C13 1.3887(15) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.3899(14) .
C14 C19 1.3996(14) .
C15 C16 1.3955(15) .
C15 H15 0.9500 .
C16 C17 1.3809(18) .
C16 H16 0.9500 .
C17 C18 1.3859(18) .
C17 H17 0.9500 .
C18 C19 1.3860(15) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.3900 .
C20 C25 1.3900 .
C20 C26 1.493(5) .
C21 C22 1.3900 .
C21 H21 0.9500 .
C22 C23 1.3900 .
C22 H22 0.9500 .
C23 C24 1.3900 .
C23 H23 0.9500 .
C24 C25 1.3900 .
C24 H24 0.9500 .
C25 H25 0.9500 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
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_4
N1A C1A N1A C1A -59(31) 2_655 2_655
C1A C1A N1A N1A 59(31) 2_655 2_655
P1 N2 P1 C8 63.26(4) 2 .
P1 N2 P1 C2 -177.13(4) 2 .
P1 N2 P1 C14 -62.35(4) 2 .
N2 P1 C2 C7 -0.31(9) . .
C8 P1 C2 C7 121.28(9) . .
C14 P1 C2 C7 -120.54(9) . .
N2 P1 C2 C3 175.92(8) . .
C8 P1 C2 C3 -62.48(10) . .
C14 P1 C2 C3 55.70(10) . .
C7 C2 C3 C4 0.52(17) . .
P1 C2 C3 C4 -175.75(10) . .
C2 C3 C4 C5 0.1(2) . .
C3 C4 C5 C6 -0.5(2) . .
C4 C5 C6 C7 0.3(2) . .
C3 C2 C7 C6 -0.75(16) . .
P1 C2 C7 C6 175.42(9) . .
C5 C6 C7 C2 0.34(17) . .
N2 P1 C8 C9 86.05(9) . .
C2 P1 C8 C9 -32.55(9) . .
C14 P1 C8 C9 -147.00(8) . .
N2 P1 C8 C13 -82.36(9) . .
C2 P1 C8 C13 159.04(8) . .
C14 P1 C8 C13 44.59(9) . .
C13 C8 C9 C10 0.81(15) . .
P1 C8 C9 C10 -167.69(8) . .
C8 C9 C10 C11 -0.48(17) . .
C9 C10 C11 C12 -0.84(18) . .
C10 C11 C12 C13 1.84(18) . .
C11 C12 C13 C8 -1.49(16) . .
C9 C8 C13 C12 0.18(15) . .
P1 C8 C13 C12 168.50(8) . .
N2 P1 C14 C15 137.46(9) . .
C8 P1 C14 C15 10.97(10) . .
C2 P1 C14 C15 -106.18(10) . .
N2 P1 C14 C19 -43.83(9) . .
C8 P1 C14 C19 -170.32(8) . .
C2 P1 C14 C19 72.53(9) . .
C19 C14 C15 C16 0.88(16) . .
P1 C14 C15 C16 179.55(9) . .
C14 C15 C16 C17 -1.22(18) . .
C15 C16 C17 C18 0.82(18) . .
C16 C17 C18 C19 -0.09(18) . .
C17 C18 C19 C14 -0.24(17) . .
C15 C14 C19 C18 -0.16(16) . .
P1 C14 C19 C18 -178.94(8) . .
C25 C20 C21 C22 0.0 . .
C26 C20 C21 C22 -177.9(3) . .
C20 C21 C22 C23 0.0 . .
C21 C22 C23 C24 0.0 . .
C22 C23 C24 C25 0.0 . .
C23 C24 C25 C20 0.0 . .
C21 C20 C25 C24 0.0 . .
C26 C20 C25 C24 178.0(3) . .
