#------------------------------------------------------------------------------
#$Date: 2022-05-05 01:59:53 +0300 (Thu, 05 May 2022) $
#$Revision: 274901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/01/7710184.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_7710184
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         'C14 H16 Bi N'
_chemical_formula_sum            'C14 H16 Bi N'
_chemical_formula_weight         407.26
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-12
_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                80.019(3)
_cell_angle_beta                 78.242(3)
_cell_angle_gamma                88.274(3)
_cell_formula_units_Z            4
_cell_length_a                   9.3621(4)
_cell_length_b                   9.7525(3)
_cell_length_c                   14.8523(6)
_cell_measurement_reflns_used    18869
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.179
_cell_measurement_theta_min      2.120
_cell_volume                     1307.51(9)
_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                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'STOE IPDS 2T'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.179
_diffrn_reflns_theta_min         2.120
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    13.458
_exptl_absorpt_correction_T_max  0.1075
_exptl_absorpt_correction_T_min  0.0355
_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    2.069
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_rad          0.0569
_refine_diff_density_max         1.833
_refine_diff_density_min         -1.547
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         7042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0270
_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)+(0.0333P)²+2.1903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5603
_reflns_number_total             7042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00472k2.cif
_cod_data_source_block           tdx049
_cod_database_code               7710184
_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.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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 0.79590(2) 0.33654(2) 0.21662(2) 0.01677(5) Uani 1 1 d . . . . .
N1 N 0.5963(4) 0.4640(4) 0.2035(3) 0.0203(7) Uani 1 1 d . . . . .
C1 C 0.7522(4) 0.2891(4) 0.3733(3) 0.0185(8) Uani 1 1 d . . . . .
C2 C 0.9478(5) 0.5200(4) 0.1983(3) 0.0194(8) Uani 1 1 d . . . . .
C5 C 0.5674(5) 0.5756(4) 0.2585(4) 0.0258(10) Uani 1 1 d . . . . .
H5A H 0.550097 0.535731 0.325057 0.039 Uiso 1 1 calc GR . . . .
H5B H 0.481021 0.627376 0.244423 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.651696 0.638680 0.242918 0.039 Uiso 1 1 calc GR . . . .
C6 C 0.6100(5) 0.5257(5) 0.1045(4) 0.0269(10) Uani 1 1 d . . . . .
H6A H 0.689958 0.593913 0.086348 0.040 Uiso 1 1 calc GR . . . .
H6B H 0.518685 0.572056 0.094876 0.040 Uiso 1 1 calc GR . . . .
H6C H 0.630687 0.452291 0.066260 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.7463(4) 0.1484(4) 0.4132(3) 0.0186(8) Uani 1 1 d . . . . .
H9 H 0.758735 0.079649 0.374134 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7225(5) 0.1079(4) 0.5095(3) 0.0209(8) Uani 1 1 d . . . . .
H10 H 0.719034 0.011786 0.535920 0.025 Uiso 1 1 calc R . . . .
C11 C 0.7037(5) 0.2076(4) 0.5670(3) 0.0214(9) Uani 1 1 d . . . . .
H11 H 0.686166 0.179892 0.632865 0.026 Uiso 1 1 calc R . . . .
C12 C 0.7106(5) 0.3480(4) 0.5281(3) 0.0190(8) Uani 1 1 d . . . . .
H12 H 0.699058 0.416311 0.567505 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7342(4) 0.3889(4) 0.4320(3) 0.0182(8) Uani 1 1 d . . . . .
H13 H 0.738094 0.485097 0.405877 0.022 Uiso 1 1 calc R . . . .
C14 C 1.0082(5) 0.5597(4) 0.2688(3) 0.0211(8) Uani 1 1 d . . . . .
H14 H 0.977322 0.514737 0.331664 0.025 Uiso 1 1 calc R . . . .
C15 C 1.1127(5) 0.6642(5) 0.2476(4) 0.0256(9) Uani 1 1 d . . . . .
H15 H 1.150741 0.691981 0.296280 0.031 Uiso 1 1 calc R . . . .
C16 C 1.1623(5) 0.7286(5) 0.1565(4) 0.0270(10) Uani 1 1 d . . . . .
H16 H 1.237143 0.797136 0.142357 0.032 Uiso 1 1 calc R . . . .
C17 C 1.1018(6) 0.6923(5) 0.0856(4) 0.0291(10) Uani 1 1 d . . . . .
H17 H 1.132142 0.738372 0.022934 0.035 Uiso 1 1 calc R . . . .
C18 C 0.9971(5) 0.5885(5) 0.1076(4) 0.0255(9) Uani 1 1 d . . . . .
H18 H 0.957390 0.562918 0.058800 0.031 Uiso 1 1 calc R . . . .
Bi2 Bi 0.29692(2) 0.32525(2) 0.20922(2) 0.01928(5) Uani 1 1 d . . . . .
N2 N 0.1055(4) 0.1952(4) 0.2064(3) 0.0230(8) Uani 1 1 d . . . . .
C3 C 0.2571(5) 0.2830(4) 0.3655(3) 0.0201(9) Uani 1 1 d . . . . .
C4 C 0.4618(5) 0.1548(4) 0.1845(3) 0.0205(8) Uani 1 1 d . . . . .
C7 C 0.1121(5) 0.1859(5) 0.1084(4) 0.0292(10) Uani 1 1 d . . . . .
H7A H 0.122774 0.279467 0.070910 0.044 Uiso 1 1 calc GR . . . .
H7B H 0.022160 0.142848 0.102223 0.044 Uiso 1 1 calc GR . . . .
H7C H 0.195890 0.129030 0.086517 0.044 Uiso 1 1 calc GR . . . .
C8 C 0.1006(5) 0.0542(5) 0.2605(4) 0.0283(10) Uani 1 1 d . . . . .
H8A H 0.187220 0.002861 0.235882 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.012710 0.006111 0.255633 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.098415 0.059278 0.326038 0.042 Uiso 1 1 calc GR . . . .
C19 C 0.1171(5) 0.2631(5) 0.4180(3) 0.0230(9) Uani 1 1 d . . . . .
H19 H 0.037332 0.264409 0.387240 0.028 Uiso 1 1 calc R . . . .
C20 C 0.0909(5) 0.2410(5) 0.5150(4) 0.0255(9) Uani 1 1 d . . . . .
H20 H -0.005902 0.225915 0.550072 0.031 Uiso 1 1 calc R . . . .
C21 C 0.2065(5) 0.2413(4) 0.5605(3) 0.0228(9) Uani 1 1 d . . . . .
H21 H 0.189289 0.227025 0.626784 0.027 Uiso 1 1 calc R . . . .
C22 C 0.3472(5) 0.2624(4) 0.5086(3) 0.0225(9) Uani 1 1 d . . . . .
H22 H 0.426643 0.262363 0.539432 0.027 Uiso 1 1 calc R . . . .
C23 C 0.3729(5) 0.2836(4) 0.4116(3) 0.0208(8) Uani 1 1 d . . . . .
H23 H 0.469688 0.298557 0.376519 0.025 Uiso 1 1 calc R . . . .
C24 C 0.5243(5) 0.1468(5) 0.0912(3) 0.0261(10) Uani 1 1 d . . . . .
H24 H 0.494493 0.209381 0.042044 0.031 Uiso 1 1 calc R . . . .
C25 C 0.6306(6) 0.0466(5) 0.0707(4) 0.0303(11) Uani 1 1 d . . . . .
H25 H 0.672679 0.041314 0.007539 0.036 Uiso 1 1 calc R . . . .
C26 C 0.6745(6) -0.0448(5) 0.1420(4) 0.0293(11) Uani 1 1 d . . . . .
H26 H 0.747894 -0.111632 0.127841 0.035 Uiso 1 1 calc R . . . .
C27 C 0.6115(5) -0.0388(5) 0.2339(4) 0.0275(10) Uani 1 1 d . . . . .
H27 H 0.640154 -0.102846 0.282813 0.033 Uiso 1 1 calc R . . . .
C28 C 0.5066(5) 0.0603(4) 0.2547(3) 0.0225(9) Uani 1 1 d . . . . .
H28 H 0.464410 0.063725 0.318056 0.027 Uiso 1 1 calc R . . . .
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 96.94(14) . . ?
N1 Bi1 C2 95.67(14) . . ?
C1 Bi1 C2 97.27(16) . . ?
C5 N1 Bi1 116.7(3) . . ?
C5 N1 C6 108.3(4) . . ?
C6 N1 Bi1 107.4(3) . . ?
C9 C1 Bi1 116.0(3) . . ?
C9 C1 C13 118.9(4) . . ?
C13 C1 Bi1 125.1(3) . . ?
C14 C2 Bi1 125.4(3) . . ?
C18 C2 Bi1 116.6(3) . . ?
C18 C2 C14 117.6(4) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C9 H9 119.7 . . ?
C10 C9 C1 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C1 C13 H13 119.8 . . ?
C12 C13 C1 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C2 C14 H14 119.8 . . ?
C15 C14 C2 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.0(5) . . ?
C18 C17 H17 120.5 . . ?
C2 C18 H18 118.8 . . ?
C17 C18 C2 122.4(5) . . ?
C17 C18 H18 118.8 . . ?
N2 Bi2 C3 92.53(15) . . ?
N2 Bi2 C4 94.52(15) . . ?
C3 Bi2 C4 97.12(16) . . ?
C7 N2 Bi2 106.3(3) . . ?
C7 N2 C8 108.8(4) . . ?
C8 N2 Bi2 115.5(3) . . ?
C19 C3 Bi2 120.8(3) . . ?
C19 C3 C23 118.8(4) . . ?
C23 C3 Bi2 120.4(3) . . ?
C24 C4 Bi2 116.9(3) . . ?
C28 C4 Bi2 124.7(3) . . ?
C28 C4 C24 118.4(4) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C19 H19 119.4 . . ?
C3 C19 C20 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(5) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C3 C23 H23 119.9 . . ?
C22 C23 C3 120.3(4) . . ?
C22 C23 H23 119.9 . . ?
C4 C24 H24 120.0 . . ?
C25 C24 C4 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(5) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.9(4) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.1(5) . . ?
C28 C27 H27 119.9 . . ?
C4 C28 H28 119.4 . . ?
C27 C28 C4 121.2(4) . . ?
C27 C28 H28 119.4 . . ?
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 2.236(4) . ?
Bi1 C1 2.247(5) . ?
Bi1 C2 2.263(4) . ?
N1 C5 1.457(5) . ?
N1 C6 1.470(6) . ?
C1 C9 1.395(6) . ?
C1 C13 1.399(6) . ?
C2 C14 1.402(6) . ?
C2 C18 1.389(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.389(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.384(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C18 H18 0.9500 . ?
Bi2 N2 2.238(4) . ?
Bi2 C3 2.241(5) . ?
Bi2 C4 2.260(4) . ?
N2 C7 1.462(6) . ?
N2 C8 1.464(6) . ?
C3 C19 1.382(6) . ?
C3 C23 1.396(6) . ?
C4 C24 1.404(6) . ?
C4 C28 1.391(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.392(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(7) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.399(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(6) . ?
C28 H28 0.9500 . ?
