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#$Date: 2022-06-24 02:12:50 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/05/7710560.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_7710560
loop_
_publ_author_name
'Duneș, Gabriel'
'Soran, Albert'
'Silvestru, Cristian'
_publ_section_title
;
 Organopnictogen(III) bis(arylthiolates) containing NCN-aryl pincer
 ligands: from synthesis and characterization to reactivity
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01436J
_journal_year                    2022
_chemical_formula_moiety         'C16 H23 Bi I2 N2 O2, 0.5(I2)'
_chemical_formula_sum            'C16 H23 Bi I3 N2 O2'
_chemical_formula_weight         865.04
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-02-17 deposited with the CCDC.	2022-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.5660(10)
_cell_angle_beta                 94.0610(10)
_cell_angle_gamma                109.3520(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1472(2)
_cell_length_b                   9.8243(2)
_cell_length_c                   13.1662(3)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    295.(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.37
_cell_volume                     1112.83(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX4 2021.10-0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'Bruker APEX4 2021.10-0'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_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            39183
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'Incoatec Mo--I\mS 3.0 microfocus source'
_exptl_absorpt_coefficient_mu    12.094
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             782
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.057
_refine_diff_density_max         1.096
_refine_diff_density_min         -1.557
_refine_ls_extinction_coef       0.00153(13)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0269
_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)+(0.0266P)²+3.8493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5187
_reflns_number_total             5515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01436j2.cif
_cod_data_source_block           0166alb
_cod_database_code               7710560
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi1 0.36991(2) 0.63643(2) 0.82505(2) 0.03523(6) Uani d . . . 1 . .
I I1 0.60871(4) 0.48516(4) 0.85384(3) 0.05125(10) Uani d . . . 1 . .
I I2 0.11905(5) 0.78618(5) 0.79546(4) 0.06798(12) Uani d . . . 1 . .
I I3 0.05193(6) 0.93181(5) 0.57956(5) 0.08118(16) Uani d . . . 1 . .
O O1 0.6622(5) 1.0958(5) 0.9060(4) 0.0740(14) Uani d . . . 1 . .
O O2 0.0634(5) 0.2026(5) 0.9241(4) 0.0716(13) Uani d . . . 1 . .
N N1 0.5969(5) 0.8516(5) 0.7659(4) 0.0503(11) Uani d . . . 1 . .
N N2 0.1333(5) 0.4092(5) 0.7656(3) 0.0461(10) Uani d . . . 1 . .
C C1 0.3638(7) 0.6155(6) 0.6578(4) 0.0481(12) Uani d . . . 1 . .
C C2 0.4917(8) 0.7002(7) 0.6097(4) 0.0588(15) Uani d . . . 1 . .
C C3 0.4840(12) 0.6887(10) 0.5033(6) 0.083(2) Uani d . . . 1 . .
H H3 0.566587 0.746115 0.468982 0.100000 Uiso calc U . R 1 . .
C C4 0.3566(13) 0.5939(11) 0.4486(6) 0.095(3) Uani d . . . 1 . .
H H4 0.354178 0.586504 0.377962 0.114000 Uiso calc U . R 1 . .
C C5 0.2310(12) 0.5090(10) 0.4995(5) 0.083(2) Uani d . . . 1 . .
H H5 0.145426 0.444114 0.462577 0.099000 Uiso calc U . R 1 . .
C C6 0.2330(8) 0.5207(7) 0.6053(4) 0.0562(14) Uani d . . . 1 . .
C C7 0.6329(8) 0.7916(7) 0.6711(5) 0.0647(17) Uani d . . . 1 . .
H H7A 0.699056 0.734464 0.688379 0.078000 Uiso calc U . R 1 . .
H H7B 0.690205 0.870456 0.630401 0.078000 Uiso calc U . R 1 . .
C C8 0.7382(6) 0.9017(7) 0.8383(5) 0.0595(15) Uani d . . . 1 . .
H H8A 0.823073 0.968086 0.804809 0.071000 Uiso calc U . R 1 . .
H H8B 0.768623 0.819772 0.858797 0.071000 Uiso calc U . R 1 . .
C C9 0.7076(7) 0.9758(7) 0.9308(6) 0.0649(16) Uani d . . . 1 . .
H H9A 0.626361 0.907428 0.965964 0.078000 Uiso calc U . R 1 . .
H H9B 0.800942 1.007224 0.976910 0.078000 Uiso calc U . R 1 . .
C C10 0.5258(8) 1.0506(7) 0.8394(6) 0.0678(18) Uani d . . . 1 . .
H H10A 0.495493 1.133703 0.822028 0.081000 Uiso calc U . R 1 . .
H H10B 0.442426 0.984071 0.874040 0.081000 Uiso calc U . R 1 . .
C C11 0.5475(7) 0.9781(6) 0.7434(5) 0.0604(15) Uani d . . . 1 . .
H H11A 0.450572 0.947075 0.700800 0.073000 Uiso calc U . R 1 . .
H H11B 0.625266 1.046718 0.706055 0.073000 Uiso calc U . R 1 . .
C C12 0.0936(8) 0.4419(7) 0.6604(5) 0.0634(16) Uani d . . . 1 . .
H H12A 0.026071 0.499833 0.661793 0.076000 Uiso calc U . R 1 . .
H H12B 0.036433 0.352211 0.623073 0.076000 Uiso calc U . R 1 . .
C C13 0.1792(7) 0.2780(6) 0.7666(5) 0.0577(14) Uani d . . . 1 . .
H H13A 0.276203 0.297834 0.734654 0.069000 Uiso calc U . R 1 . .
H H13B 0.100501 0.200915 0.727005 0.069000 Uiso calc U . R 1 . .
C C14 0.1988(8) 0.2297(7) 0.8719(6) 0.0648(17) Uani d . . . 1 . .
H H14A 0.225987 0.142412 0.868877 0.078000 Uiso calc U . R 1 . .
H H14B 0.283834 0.303444 0.909616 0.078000 Uiso calc U . R 1 . .
C C15 0.0227(7) 0.3294(7) 0.9284(5) 0.0606(15) Uani d . . . 1 . .
H H15A 0.105999 0.405133 0.965862 0.073000 Uiso calc U . R 1 . .
H H15B -0.070073 0.310706 0.964864 0.073000 Uiso calc U . R 1 . .
C C16 -0.0061(6) 0.3794(7) 0.8246(5) 0.0574(14) Uani d . . . 1 . .
H H16A -0.093161 0.305880 0.788388 0.069000 Uiso calc U . R 1 . .
H H16B -0.033240 0.466395 0.830653 0.069000 Uiso calc U . R 1 . .
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'
I I -0.4742 1.8119 '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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Bi1 N1 . . 72.6(2) ?
C1 Bi1 N2 . . 72.56(19) ?
N1 Bi1 N2 . . 145.14(16) ?
C1 Bi1 I1 . . 91.89(14) ?
N1 Bi1 I1 . . 85.35(10) ?
N2 Bi1 I1 . . 97.14(10) ?
C1 Bi1 I2 . . 88.11(14) ?
N1 Bi1 I2 . . 95.73(10) ?
N2 Bi1 I2 . . 81.78(10) ?
I1 Bi1 I2 . . 178.872(12) ?
C9 O1 C10 . . 109.4(5) ?
C14 O2 C15 . . 109.4(5) ?
C7 N1 C11 . . 110.2(5) ?
C7 N1 C8 . . 110.0(5) ?
C11 N1 C8 . . 107.5(5) ?
C7 N1 Bi1 . . 102.2(3) ?
C11 N1 Bi1 . . 111.6(3) ?
C8 N1 Bi1 . . 115.3(3) ?
C12 N2 C13 . . 110.4(5) ?
C12 N2 C16 . . 109.2(5) ?
C13 N2 C16 . . 107.5(5) ?
C12 N2 Bi1 . . 102.9(3) ?
C13 N2 Bi1 . . 110.6(3) ?
C16 N2 Bi1 . . 116.3(3) ?
C6 C1 C2 . . 122.9(5) ?
C6 C1 Bi1 . . 118.8(4) ?
C2 C1 Bi1 . . 118.3(4) ?
C1 C2 C3 . . 117.5(7) ?
C1 C2 C7 . . 120.0(5) ?
C3 C2 C7 . . 122.4(7) ?
C4 C3 C2 . . 121.3(8) ?
C4 C3 H3 . . 119.400000 ?
C2 C3 H3 . . 119.400000 ?
C3 C4 C5 . . 119.7(7) ?
C3 C4 H4 . . 120.100000 ?
C5 C4 H4 . . 120.100000 ?
C6 C5 C4 . . 120.5(8) ?
C6 C5 H5 . . 119.700000 ?
C4 C5 H5 . . 119.700000 ?
C1 C6 C5 . . 118.1(7) ?
C1 C6 C12 . . 120.4(5) ?
C5 C6 C12 . . 121.4(7) ?
N1 C7 C2 . . 112.7(5) ?
N1 C7 H7A . . 109.000000 ?
C2 C7 H7A . . 109.000000 ?
N1 C7 H7B . . 109.000000 ?
C2 C7 H7B . . 109.000000 ?
H7A C7 H7B . . 107.800000 ?
N1 C8 C9 . . 110.6(5) ?
N1 C8 H8A . . 109.500000 ?
C9 C8 H8A . . 109.500000 ?
N1 C8 H8B . . 109.500000 ?
C9 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 108.100000 ?
O1 C9 C8 . . 112.3(6) ?
O1 C9 H9A . . 109.100000 ?
C8 C9 H9A . . 109.100000 ?
O1 C9 H9B . . 109.100000 ?
C8 C9 H9B . . 109.100000 ?
H9A C9 H9B . . 107.900000 ?
O1 C10 C11 . . 112.2(6) ?
O1 C10 H10A . . 109.200000 ?
C11 C10 H10A . . 109.200000 ?
O1 C10 H10B . . 109.200000 ?
C11 C10 H10B . . 109.200000 ?
H10A C10 H10B . . 107.900000 ?
N1 C11 C10 . . 111.4(5) ?
N1 C11 H11A . . 109.400000 ?
C10 C11 H11A . . 109.400000 ?
N1 C11 H11B . . 109.400000 ?
C10 C11 H11B . . 109.400000 ?
H11A C11 H11B . . 108.000000 ?
N2 C12 C6 . . 113.2(5) ?
N2 C12 H12A . . 108.900000 ?
C6 C12 H12A . . 108.900000 ?
N2 C12 H12B . . 108.900000 ?
C6 C12 H12B . . 108.900000 ?
H12A C12 H12B . . 107.800000 ?
N2 C13 C14 . . 111.9(5) ?
N2 C13 H13A . . 109.200000 ?
C14 C13 H13A . . 109.200000 ?
N2 C13 H13B . . 109.200000 ?
C14 C13 H13B . . 109.200000 ?
H13A C13 H13B . . 107.900000 ?
O2 C14 C13 . . 112.4(5) ?
O2 C14 H14A . . 109.100000 ?
C13 C14 H14A . . 109.100000 ?
O2 C14 H14B . . 109.100000 ?
C13 C14 H14B . . 109.100000 ?
H14A C14 H14B . . 107.900000 ?
O2 C15 C16 . . 111.8(6) ?
O2 C15 H15A . . 109.300000 ?
C16 C15 H15A . . 109.300000 ?
O2 C15 H15B . . 109.300000 ?
C16 C15 H15B . . 109.300000 ?
H15A C15 H15B . . 107.900000 ?
N2 C16 C15 . . 111.2(5) ?
N2 C16 H16A . . 109.400000 ?
C15 C16 H16A . . 109.400000 ?
N2 C16 H16B . . 109.400000 ?
C15 C16 H16B . . 109.400000 ?
H16A C16 H16B . . 108.000000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 C1 . 2.204(5) ?
Bi1 N1 . 2.596(4) ?
Bi1 N2 . 2.608(4) ?
Bi1 I1 . 3.0279(4) ?
Bi1 I2 . 3.1151(4) ?
I3 I3 2_576 2.7756(13) ?
O1 C9 . 1.408(8) ?
O1 C10 . 1.412(8) ?
O2 C14 . 1.408(8) ?
O2 C15 . 1.415(8) ?
N1 C7 . 1.479(8) ?
N1 C11 . 1.483(7) ?
N1 C8 . 1.488(8) ?
N2 C12 . 1.472(7) ?
N2 C13 . 1.483(7) ?
N2 C16 . 1.488(7) ?
C1 C6 . 1.382(8) ?
C1 C2 . 1.390(8) ?
C2 C3 . 1.398(9) ?
C2 C7 . 1.483(10) ?
C3 C4 . 1.376(13) ?
C3 H3 . 0.930000 ?
C4 C5 . 1.397(14) ?
C4 H4 . 0.930000 ?
C5 C6 . 1.395(8) ?
C5 H5 . 0.930000 ?
C6 C12 . 1.496(10) ?
C7 H7A . 0.970000 ?
C7 H7B . 0.970000 ?
C8 C9 . 1.503(10) ?
C8 H8A . 0.970000 ?
C8 H8B . 0.970000 ?
C9 H9A . 0.970000 ?
C9 H9B . 0.970000 ?
C10 C11 . 1.502(10) ?
C10 H10A . 0.970000 ?
C10 H10B . 0.970000 ?
C11 H11A . 0.970000 ?
C11 H11B . 0.970000 ?
C12 H12A . 0.970000 ?
C12 H12B . 0.970000 ?
C13 C14 . 1.488(9) ?
C13 H13A . 0.970000 ?
C13 H13B . 0.970000 ?
C14 H14A . 0.970000 ?
C14 H14B . 0.970000 ?
C15 C16 . 1.492(9) ?
C15 H15A . 0.970000 ?
C15 H15B . 0.970000 ?
C16 H16A . 0.970000 ?
C16 H16B . 0.970000 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.9(9) ?
Bi1 C1 C2 C3 . . . . -178.2(5) ?
C6 C1 C2 C7 . . . . -175.4(6) ?
Bi1 C1 C2 C7 . . . . 5.4(7) ?
C1 C2 C3 C4 . . . . -1.9(11) ?
C7 C2 C3 C4 . . . . 174.4(7) ?
C2 C3 C4 C5 . . . . 1.0(13) ?
C3 C4 C5 C6 . . . . 0.8(12) ?
C2 C1 C6 C5 . . . . 0.8(9) ?
Bi1 C1 C6 C5 . . . . 179.9(5) ?
C2 C1 C6 C12 . . . . -174.7(6) ?
Bi1 C1 C6 C12 . . . . 4.4(7) ?
C4 C5 C6 C1 . . . . -1.6(10) ?
C4 C5 C6 C12 . . . . 173.8(7) ?
C11 N1 C7 C2 . . . . -79.3(6) ?
C8 N1 C7 C2 . . . . 162.3(5) ?
Bi1 N1 C7 C2 . . . . 39.3(6) ?
C1 C2 C7 N1 . . . . -34.9(8) ?
C3 C2 C7 N1 . . . . 148.9(6) ?
C7 N1 C8 C9 . . . . 174.6(5) ?
C11 N1 C8 C9 . . . . 54.6(6) ?
Bi1 N1 C8 C9 . . . . -70.6(5) ?
C10 O1 C9 C8 . . . . 59.2(7) ?
N1 C8 C9 O1 . . . . -59.0(7) ?
C9 O1 C10 C11 . . . . -58.3(7) ?
C7 N1 C11 C10 . . . . -174.2(5) ?
C8 N1 C11 C10 . . . . -54.3(6) ?
Bi1 N1 C11 C10 . . . . 73.1(5) ?
O1 C10 C11 N1 . . . . 57.8(7) ?
C13 N2 C12 C6 . . . . -81.6(6) ?
C16 N2 C12 C6 . . . . 160.5(5) ?
Bi1 N2 C12 C6 . . . . 36.4(6) ?
C1 C6 C12 N2 . . . . -32.0(8) ?
C5 C6 C12 N2 . . . . 152.6(6) ?
C12 N2 C13 C14 . . . . -172.0(5) ?
C16 N2 C13 C14 . . . . -53.1(6) ?
Bi1 N2 C13 C14 . . . . 74.8(5) ?
C15 O2 C14 C13 . . . . -58.6(7) ?
N2 C13 C14 O2 . . . . 57.3(7) ?
C14 O2 C15 C16 . . . . 59.4(7) ?
C12 N2 C16 C15 . . . . 173.6(5) ?
C13 N2 C16 C15 . . . . 53.8(6) ?
Bi1 N2 C16 C15 . . . . -70.7(5) ?
O2 C15 C16 N2 . . . . -58.9(6) ?
