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#$Date: 2022-05-05 01:59:53 +0300 (Thu, 05 May 2022) $
#$Revision: 274901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/01/7710188.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_7710188
loop_
_publ_author_name
'Dunaj, Tobias'
'Dollberg, Kevin'
'von Hänisch, Carsten'
_publ_section_title
;
 Binary interpnictogen compounds bearing diaryl bismuth fragments bound to
 all lighter pnictogens
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00472K
_journal_year                    2022
_chemical_formula_moiety         'C22 H32 Bi N'
_chemical_formula_sum            'C22 H32 Bi N'
_chemical_formula_weight         519.46
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Light-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-11 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                96.380(4)
_cell_angle_beta                 104.891(4)
_cell_angle_gamma                115.291(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5236(5)
_cell_length_b                   9.9232(5)
_cell_length_c                   13.0242(6)
_cell_measurement_reflns_used    16312
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.151
_cell_measurement_theta_min      1.972
_cell_volume                     1040.56(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         1.672
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           0.000
_diffrn_source_power             0.000
_diffrn_source_voltage           0
_exptl_absorpt_coefficient_mu    8.475
_exptl_absorpt_correction_T_max  0.2473
_exptl_absorpt_correction_T_min  0.0727
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'LANA 1.83.8.0 (STOE, 2020)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       irregular
_exptl_crystal_F_000             508
_exptl_crystal_size_rad          0.0701
_refine_diff_density_max         1.291
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4916
_reflns_number_total             5617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00472k2.cif
_cod_data_source_block           tdx024
_cod_original_cell_volume        1040.56(10)
_cod_database_code               7710188
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.96 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C5(H5), C12(H12)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C21(H21A,H21B,
 H21C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C22(H22A,
 H22B,H22C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Bi1 Bi 0.54700(2) 0.63142(2) 0.69428(2) 0.02223(4) Uani 1 1 d . . . . .
N1 N 0.5613(4) 0.8534(3) 0.7576(2) 0.0258(6) Uani 1 1 d D . . . .
C9 C 0.7907(4) 0.6238(4) 0.5689(3) 0.0246(6) Uani 1 1 d . . . . .
C7 C 1.0323(4) 0.8108(4) 0.9779(3) 0.0247(6) Uani 1 1 d . . . . .
H7 H 1.140550 0.895217 1.001033 0.030 Uiso 1 1 calc R . . . .
C6 C 0.9954(4) 0.7031(4) 1.0405(3) 0.0267(7) Uani 1 1 d . . . . .
C1 C 0.7541(4) 0.6732(4) 0.8476(3) 0.0234(6) Uani 1 1 d . . . . .
C16 C 0.9684(4) 0.9198(4) 0.8193(3) 0.0271(7) Uani 1 1 d . . . . .
H16A H 1.061668 1.015288 0.869543 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.876238 0.939107 0.786131 0.041 Uiso 1 1 calc GR . . . .
H16C H 1.001801 0.883496 0.761363 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.8747(4) 0.6543(4) 0.4941(3) 0.0263(7) Uani 1 1 d . . . . .
H10 H 0.939484 0.605040 0.487716 0.032 Uiso 1 1 calc R . . . .
C8 C 0.9146(4) 0.7978(4) 0.8824(3) 0.0248(6) Uani 1 1 d . . . . .
C5 C 0.8352(4) 0.5827(4) 1.0057(3) 0.0266(7) Uani 1 1 d . . . . .
H5 H 0.806411 0.509990 1.048359 0.032 Uiso 1 1 calc R . . . .
C2 C 0.6951(4) 0.6970(4) 0.5794(3) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.7694(5) 0.8223(4) 0.4387(3) 0.0300(7) Uani 1 1 d . . . . .
H12 H 0.761128 0.889895 0.394053 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4097(4) 0.8422(4) 0.7763(3) 0.0258(6) Uani 1 1 d . . . . .
C4 C 0.7158(4) 0.5658(4) 0.9101(3) 0.0249(6) Uani 1 1 d . . . . .
C17 C 0.8073(5) 0.5134(4) 0.6361(3) 0.0307(7) Uani 1 1 d . . . . .
H17A H 0.843927 0.449071 0.599787 0.046 Uiso 1 1 calc GR . . . .
H17B H 0.700302 0.447799 0.642609 0.046 Uiso 1 1 calc GR . . . .
H17C H 0.888571 0.571825 0.709380 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.8673(4) 0.7542(4) 0.4285(3) 0.0274(7) Uani 1 1 d . . . . .
C14 C 0.5451(5) 0.4283(4) 0.8773(3) 0.0314(7) Uani 1 1 d . . . . .
H14A H 0.463785 0.464554 0.875748 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.543698 0.365967 0.930746 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.517570 0.365716 0.804322 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.6830(4) 0.7950(4) 0.5121(3) 0.0268(7) Uani 1 1 d . . . . .
C21 C 0.4481(5) 1.0063(4) 0.8283(3) 0.0335(8) Uani 1 1 d . . . . .
H21A H 0.532715 1.044355 0.901202 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.347470 1.005052 0.835258 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.488421 1.074167 0.781657 0.050 Uiso 1 1 calc GR . . . .
C15 C 1.1248(5) 0.7179(4) 1.1417(3) 0.0305(7) Uani 1 1 d . . . . .
H15A H 1.208679 0.700318 1.120988 0.046 Uiso 1 1 calc GR . . . .
H15B H 1.073650 0.641368 1.180306 0.046 Uiso 1 1 calc GR . . . .
H15C H 1.176751 0.821505 1.190086 0.046 Uiso 1 1 calc GR . . . .
C19 C 0.5784(5) 0.8730(5) 0.5161(3) 0.0341(8) Uani 1 1 d . . . . .
H19A H 0.467533 0.796439 0.510497 0.051 Uiso 1 1 calc GR . . . .
H19B H 0.571023 0.921598 0.454829 0.051 Uiso 1 1 calc GR . . . .
H19C H 0.628742 0.951724 0.585687 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.9591(5) 0.7842(5) 0.3480(3) 0.0372(8) Uani 1 1 d . . . . .
H18A H 1.040516 0.747004 0.364501 0.056 Uiso 1 1 calc GR . . . .
H18B H 1.015575 0.895075 0.353868 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.880824 0.730022 0.273264 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.3548(6) 0.7393(5) 0.8530(4) 0.0403(9) Uani 1 1 d . . . . .
H22A H 0.327103 0.633658 0.819596 0.060 Uiso 1 1 calc GR . . . .
H22B H 0.257579 0.740150 0.864765 0.060 Uiso 1 1 calc GR . . . .
H22C H 0.444576 0.778179 0.923574 0.060 Uiso 1 1 calc GR . . . .
C20 C 0.2707(5) 0.7810(4) 0.6667(3) 0.0344(8) Uani 1 1 d . . . . .
H20A H 0.304304 0.848558 0.618451 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.172029 0.778340 0.678483 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.246056 0.676769 0.632529 0.052 Uiso 1 1 calc GR . . . .
H1 H 0.644(5) 0.883(5) 0.827(2) 0.054(14) Uiso 1 1 d D . . . .
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'
Bi Bi -4.1077 10.2566 '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'
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
_geom_angle_publ_flag
N1 Bi1 C1 90.74(11) . . ?
N1 Bi1 C2 100.55(11) . . ?
C1 Bi1 C2 98.66(12) . . ?
C3 N1 Bi1 114.9(2) . . ?
C10 C9 C2 119.1(3) . . ?
C10 C9 C17 118.1(3) . . ?
C2 C9 C17 122.7(3) . . ?
C8 C7 C6 121.8(3) . . ?
C7 C6 C15 120.9(3) . . ?
C5 C6 C7 117.7(3) . . ?
C5 C6 C15 121.4(3) . . ?
C8 C1 Bi1 124.7(2) . . ?
C4 C1 Bi1 116.3(2) . . ?
C4 C1 C8 119.1(3) . . ?
C11 C10 C9 122.5(3) . . ?
C7 C8 C1 119.5(3) . . ?
C7 C8 C16 117.6(3) . . ?
C1 C8 C16 122.9(3) . . ?
C6 C5 C4 121.8(3) . . ?
C9 C2 Bi1 117.7(2) . . ?
C13 C2 Bi1 122.9(2) . . ?
C13 C2 C9 119.1(3) . . ?
C11 C12 C13 122.2(3) . . ?
N1 C3 C21 107.1(3) . . ?
N1 C3 C22 113.3(3) . . ?
N1 C3 C20 109.3(3) . . ?
C22 C3 C21 108.8(3) . . ?
C20 C3 C21 108.8(3) . . ?
C20 C3 C22 109.4(3) . . ?
C1 C4 C14 121.9(3) . . ?
C5 C4 C1 120.2(3) . . ?
C5 C4 C14 117.9(3) . . ?
C10 C11 C18 121.2(3) . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 C18 121.5(3) . . ?
C2 C13 C19 122.0(3) . . ?
C12 C13 C2 119.7(3) . . ?
C12 C13 C19 118.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.198(3) . ?
Bi1 C1 2.268(3) . ?
Bi1 C2 2.273(3) . ?
N1 C3 1.485(4) . ?
C9 C10 1.392(5) . ?
C9 C2 1.408(5) . ?
C9 C17 1.510(5) . ?
C7 C6 1.396(5) . ?
C7 C8 1.394(5) . ?
C6 C5 1.388(5) . ?
C6 C15 1.499(5) . ?
C1 C8 1.405(5) . ?
C1 C4 1.395(4) . ?
C16 C8 1.521(5) . ?
C10 C11 1.391(5) . ?
C5 C4 1.391(5) . ?
C2 C13 1.400(4) . ?
C12 C11 1.388(5) . ?
C12 C13 1.391(5) . ?
C3 C21 1.538(5) . ?
C3 C22 1.534(5) . ?
C3 C20 1.520(5) . ?
C4 C14 1.518(5) . ?
C11 C18 1.506(5) . ?
C13 C19 1.507(5) . ?
