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#$Date: 2022-09-13 11:52:57 +0300 (Tue, 13 Sep 2022) $
#$Revision: 277800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105763.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_8105763
loop_
_publ_author_name
'Tan, Nianyuan'
'Wu, Shuisheng'
'Huiqiong, Yang'
'Lan, Donghui'
'Au, Chak-Tong'
'Yi, Bing'
_publ_section_title
;
 Crystal structure of
 6-cyclohexyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl nitrate,
 C20H23O3N2Bi
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              509
_journal_page_last               511
_journal_paper_doi               10.1515/ncrs-2018-0507
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C20 H23 Bi N2 O3'
_chemical_formula_sum            'C20 H23 Bi N2 O3'
_chemical_formula_weight         548.38
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-28 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 105.491(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6897(5)
_cell_length_b                   10.5590(5)
_cell_length_c                   17.4099(9)
_cell_measurement_reflns_used    9192
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.28
_cell_volume                     1893.71(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.959
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14351
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.279
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    9.332
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.418
_refine_diff_density_min         -2.118
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0253
_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)+(0.0195P)²+2.9960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0576
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3516
_reflns_number_total             4174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0507_suppl.cif
_cod_data_source_block           yinsf1_0m
_cod_database_code               8105763
_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.
;
_shelx_estimated_absorpt_t_max   0.767
_shelx_estimated_absorpt_t_min   0.653
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Bi1 Bi 0.99740(2) 0.27546(2) 0.04107(2) 0.02798(6) Uani 1 1 d . . . . .
N1 N 0.7606(3) 0.2827(3) 0.0321(2) 0.0278(7) Uani 1 1 d . . . . .
N2 N 1.2999(4) 0.2434(4) 0.0921(3) 0.0468(10) Uani 1 1 d . . . . .
O1 O 1.2198(3) 0.3143(4) 0.1148(2) 0.0489(8) Uani 1 1 d . . . . .
O2 O 1.2588(4) 0.1543(4) 0.0483(3) 0.0654(11) Uani 1 1 d . . . . .
O3 O 1.4140(4) 0.2673(6) 0.1160(3) 0.104(2) Uani 1 1 d . . . . .
C1 C 0.9601(4) 0.4611(4) 0.0942(2) 0.0284(8) Uani 1 1 d . . . . .
C2 C 1.0537(4) 0.5374(4) 0.1441(2) 0.0341(9) Uani 1 1 d . . . . .
H2 H 1.140489 0.513098 0.157202 0.041 Uiso 1 1 calc R . . . .
C3 C 1.0187(5) 0.6488(4) 0.1742(3) 0.0408(11) Uani 1 1 d . . . . .
H3 H 1.080823 0.697209 0.209703 0.049 Uiso 1 1 calc R . . . .
C4 C 0.8908(5) 0.6878(5) 0.1515(3) 0.0471(12) Uani 1 1 d . . . . .
H4 H 0.867252 0.764362 0.170084 0.057 Uiso 1 1 calc R . . . .
C5 C 0.7980(5) 0.6137(4) 0.1012(3) 0.0433(11) Uani 1 1 d . . . . .
H5 H 0.711924 0.640368 0.086460 0.052 Uiso 1 1 calc R . . . .
C6 C 0.8313(4) 0.5003(4) 0.0726(2) 0.0331(9) Uani 1 1 d . . . . .
C7 C 0.7285(4) 0.4196(4) 0.0175(3) 0.0366(10) Uani 1 1 d . . . . .
H7A H 0.644519 0.437010 0.026526 0.044 Uiso 1 1 calc R . . . .
H7B H 0.723842 0.440334 -0.037520 0.044 Uiso 1 1 calc R . . . .
C11 C 0.9738(4) 0.1542(4) 0.1411(2) 0.0304(9) Uani 1 1 d . . . . .
C12 C 1.0714(4) 0.0771(4) 0.1870(3) 0.0401(10) Uani 1 1 d . . . . .
H12 H 1.153524 0.077946 0.178304 0.048 Uiso 1 1 calc R . . . .
C13 C 1.0471(5) -0.0001(5) 0.2447(3) 0.0466(11) Uani 1 1 d . . . . .
H13 H 1.112556 -0.051772 0.274777 0.056 Uiso 1 1 calc R . . . .
C14 C 0.9258(5) -0.0011(5) 0.2582(3) 0.0464(12) Uani 1 1 d . . . . .
H14 H 0.909919 -0.052417 0.297985 0.056 Uiso 1 1 calc R . . . .
C15 C 0.8275(4) 0.0740(4) 0.2129(3) 0.0401(10) Uani 1 1 d . . . . .
H15 H 0.745323 0.071621 0.221378 0.048 Uiso 1 1 calc R . . . .
C16 C 0.8517(4) 0.1535(4) 0.1541(2) 0.0294(8) Uani 1 1 d . . . . .
C17 C 0.7498(4) 0.2458(4) 0.1123(3) 0.0341(10) Uani 1 1 d . . . . .
H17A H 0.664900 0.208630 0.106965 0.041 Uiso 1 1 calc R . . . .
H17B H 0.755940 0.321317 0.144792 0.041 Uiso 1 1 calc R . . . .
C21 C 0.6808(4) 0.1959(4) -0.0309(2) 0.0293(9) Uani 1 1 d . . . . .
H21 H 0.701868 0.108994 -0.012014 0.035 Uiso 1 1 calc R . . . .
C22 C 0.7152(4) 0.2078(5) -0.1097(3) 0.0414(11) Uani 1 1 d . . . . .
H22A H 0.807185 0.191697 -0.101281 0.050 Uiso 1 1 calc R . . . .
H22B H 0.697792 0.293666 -0.129509 0.050 Uiso 1 1 calc R . . . .
C23 C 0.6381(4) 0.1156(5) -0.1716(3) 0.0435(11) Uani 1 1 d . . . . .
H23A H 0.657075 0.131380 -0.222210 0.052 Uiso 1 1 calc R . . . .
H23B H 0.665158 0.029779 -0.155355 0.052 Uiso 1 1 calc R . . . .
C24 C 0.4933(4) 0.1273(5) -0.1824(3) 0.0454(11) Uani 1 1 d . . . . .
H24A H 0.463730 0.208979 -0.205780 0.054 Uiso 1 1 calc R . . . .
H24B H 0.448588 0.062045 -0.218711 0.054 Uiso 1 1 calc R . . . .
C25 C 0.4604(4) 0.1142(5) -0.1037(3) 0.0435(11) Uani 1 1 d . . . . .
H25A H 0.482539 0.029721 -0.082579 0.052 Uiso 1 1 calc R . . . .
H25B H 0.367883 0.126333 -0.111571 0.052 Uiso 1 1 calc R . . . .
C26 C 0.5350(4) 0.2120(5) -0.0442(3) 0.0416(11) Uani 1 1 d . . . . .
H26A H 0.509770 0.296561 -0.064311 0.050 Uiso 1 1 calc R . . . .
H26B H 0.513188 0.202497 0.006064 0.050 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Bi1 N1 149.99(11) . .
C1 Bi1 N1 73.19(12) . .
C1 Bi1 O1 83.75(13) . .
C11 Bi1 N1 75.05(13) . .
C11 Bi1 O1 89.02(14) . .
C11 Bi1 C1 96.32(13) . .
C7 N1 Bi1 102.9(2) . .
C7 N1 C21 113.9(3) . .
C17 N1 Bi1 105.4(2) . .
C17 N1 C7 110.1(3) . .
C17 N1 C21 110.7(3) . .
C21 N1 Bi1 113.3(2) . .
O2 N2 O1 119.1(4) . .
O3 N2 O1 118.1(5) . .
O3 N2 O2 122.8(4) . .
N2 O1 Bi1 112.5(3) . .
C2 C1 Bi1 125.8(3) . .
C6 C1 Bi1 114.8(3) . .
C6 C1 C2 119.4(4) . .
C3 C2 C1 120.5(4) . .
C2 C3 C4 119.6(4) . .
C5 C4 C3 120.2(4) . .
C4 C5 C6 120.7(4) . .
C1 C6 C7 120.2(4) . .
C5 C6 C1 119.6(4) . .
C5 C6 C7 120.2(4) . .
N1 C7 C6 110.0(3) . .
C12 C11 Bi1 124.0(3) . .
C16 C11 Bi1 116.1(3) . .
C16 C11 C12 119.9(4) . .
C13 C12 C11 120.5(4) . .
C12 C13 C14 120.0(4) . .
C13 C14 C15 120.3(4) . .
C14 C15 C16 120.1(4) . .
C11 C16 C15 119.3(4) . .
C11 C16 C17 120.9(4) . .
C15 C16 C17 119.6(4) . .
N1 C17 C16 113.5(3) . .
N1 C21 C22 112.3(3) . .
N1 C21 C26 113.6(3) . .
C22 C21 C26 109.7(4) . .
C21 C22 C23 111.8(4) . .
C24 C23 C22 112.2(4) . .
C25 C24 C23 111.0(4) . .
C24 C25 C26 110.3(4) . .
C21 C26 C25 110.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 N1 2.495(3) .
Bi1 O1 2.416(3) .
Bi1 C1 2.248(4) .
Bi1 C11 2.230(4) .
N1 C7 1.492(5) .
N1 C17 1.483(5) .
N1 C21 1.507(5) .
N2 O1 1.277(5) .
N2 O2 1.217(5) .
N2 O3 1.206(6) .
C1 C2 1.393(6) .
C1 C6 1.390(5) .
C2 C3 1.380(6) .
C3 C4 1.381(7) .
C4 C5 1.378(7) .
C5 C6 1.380(6) .
C6 C7 1.514(6) .
C11 C12 1.394(6) .
C11 C16 1.383(5) .
C12 C13 1.372(6) .
C13 C14 1.379(7) .
C14 C15 1.382(7) .
C15 C16 1.399(6) .
C16 C17 1.498(6) .
C21 C22 1.518(6) .
C21 C26 1.522(5) .
C22 C23 1.522(6) .
C23 C24 1.513(6) .
C24 C25 1.510(6) .
C25 C26 1.527(6) .
