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#$Date: 2021-05-05 11:38:42 +0300 (Wed, 05 May 2021) $
#$Revision: 264899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/68/7706887.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_7706887
loop_
_publ_author_name
'Švec, Petr'
'Samsonov, Maksim A.'
'R°uŽičková, Zdeňka'
'Brus, Jiří'
'R°uŽička, Aleš'
_publ_section_title
;
 Oxidative addition of cyanogen bromide to C,N-chelated and
 Lappert's stannylenes.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5519
_journal_page_last               5529
_journal_paper_doi               10.1039/d1dt00704a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_sum            'C21.2 H28 Br0.8 N3.2 O0.5 Sn'
_chemical_formula_weight         518.28
_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_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-07-07 deposited with the CCDC.	2021-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                94.2816(12)
_cell_angle_beta                 90.6193(10)
_cell_angle_gamma                115.8048(9)
_cell_formula_units_Z            2
_cell_length_a                   8.4177(2)
_cell_length_b                   9.2090(3)
_cell_length_c                   15.3664(5)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.47
_cell_volume                     1068.16(6)
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23476
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         1.330
_exptl_absorpt_coefficient_mu    2.706
_exptl_absorpt_correction_T_max  0.6853
_exptl_absorpt_correction_T_min  0.5307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_description       prism
_exptl_crystal_F_000             519
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.257
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0201
_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)+(0.0081P)²+0.7476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0397
_refine_ls_wR_factor_ref         0.0403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4750
_reflns_number_total             5111
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00704a2.cif
_cod_data_source_block           ps150112Sn1
_cod_depositor_comments
'Adding full bibliography for 7706886--7706890.cif.'
_cod_original_formula_sum        'C21.20 H28 Br0.80 N3.20 O0.50 Sn'
_cod_database_code               7706887
_shelx_shelxl_version_number     2017/1
_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   0.543
_shelx_estimated_absorpt_t_max   0.743
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.774
;
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
Sn1 Sn 0.64440(2) 0.61009(2) 0.75672(2) 0.01514(4) Uani 1 1 d D . . . .
Br1 Br 0.3849(2) 0.6513(3) 0.83529(14) 0.0253(3) Uani 0.36 1 d D . P A 1
N3 N 0.3162(5) 0.6666(5) 0.8558(2) 0.0319(8) Uani 0.64 1 d D . P A 2
C19 C 0.4327(13) 0.6539(16) 0.8226(9) 0.0282(18) Uani 0.64 1 d D . P A 2
Br2 Br 0.43085(16) 0.51097(16) 0.61719(6) 0.02315(19) Uani 0.44 1 d D . P A 1
C20 C 0.4626(14) 0.5188(15) 0.6439(5) 0.0284(19) Uani 0.56 1 d D . P A 2
N4 N 0.3593(6) 0.4716(6) 0.5882(3) 0.0443(13) Uani 0.56 1 d D . P A 2
N1 N 0.86073(19) 0.58581(17) 0.65529(9) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.82535(19) 0.68786(17) 0.91231(10) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.8060(2) 0.8511(2) 0.72923(12) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.8039(3) 0.9848(2) 0.77698(14) 0.0272(4) Uani 1 1 d . . . . .
H2A H 0.728505 0.969992 0.824451 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9122(3) 1.1399(2) 0.75504(15) 0.0339(5) Uani 1 1 d . . . . .
H3A H 0.911519 1.231395 0.787706 0.041 Uiso 1 1 calc R U . . .
C4 C 1.0207(3) 1.1609(2) 0.68577(16) 0.0340(5) Uani 1 1 d . . . . .
H4A H 1.094154 1.267019 0.670600 0.041 Uiso 1 1 calc R U . . .
C5 C 1.0230(2) 1.0282(2) 0.63826(14) 0.0281(4) Uani 1 1 d . . . . .
H5A H 1.099781 1.043996 0.591329 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9140(2) 0.8719(2) 0.65861(12) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.9024(2) 0.7251(2) 0.60249(12) 0.0232(4) Uani 1 1 d . . . . .
H7A H 0.809505 0.695476 0.555487 0.028 Uiso 1 1 calc R U . . .
H7B H 1.016281 0.751708 0.574799 0.028 Uiso 1 1 calc R U . . .
C8 C 0.7961(3) 0.4324(2) 0.59907(13) 0.0282(4) Uani 1 1 d . . . . .
H8A H 0.889930 0.434150 0.561346 0.042 Uiso 1 1 calc R U . . .
H8B H 0.693439 0.419460 0.562871 0.042 Uiso 1 1 calc R U . . .
H8C H 0.762010 0.341751 0.635648 0.042 Uiso 1 1 calc R U . . .
C9 C 1.0202(2) 0.6076(2) 0.70614(13) 0.0242(4) Uani 1 1 d . . . . .
H9A H 1.109786 0.606791 0.666158 0.036 Uiso 1 1 calc R U . . .
H9B H 0.990087 0.519293 0.744068 0.036 Uiso 1 1 calc R U . . .
H9C H 1.066823 0.711367 0.741997 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5980(2) 0.3888(2) 0.80960(11) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.4628(2) 0.2446(2) 0.77146(12) 0.0232(4) Uani 1 1 d . . . . .
H11A H 0.401728 0.244973 0.719185 0.028 Uiso 1 1 calc R U . . .
C12 C 0.4176(3) 0.1007(2) 0.80984(13) 0.0278(4) Uani 1 1 d . . . . .
H12A H 0.326651 0.002738 0.783382 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5043(3) 0.1000(2) 0.88619(13) 0.0269(4) Uani 1 1 d . . . . .
H13A H 0.471978 0.001823 0.912832 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6385(2) 0.2420(2) 0.92406(12) 0.0228(4) Uani 1 1 d . . . . .
H14A H 0.698063 0.240680 0.976650 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6875(2) 0.3876(2) 0.88576(11) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.8425(2) 0.5385(2) 0.92590(12) 0.0212(4) Uani 1 1 d . . . . .
H16A H 0.852844 0.530303 0.989397 0.025 Uiso 1 1 calc R U . . .
H16B H 0.952361 0.544883 0.900035 0.025 Uiso 1 1 calc R U . . .
C17 C 1.0006(2) 0.8278(2) 0.92163(13) 0.0273(4) Uani 1 1 d . . . . .
H17A H 1.079662 0.809704 0.880475 0.041 Uiso 1 1 calc R U . . .
H17B H 1.049473 0.841084 0.981449 0.041 Uiso 1 1 calc R U . . .
H17C H 0.989335 0.925844 0.909152 0.041 Uiso 1 1 calc R U . . .
C18 C 0.7119(3) 0.7125(2) 0.97876(13) 0.0268(4) Uani 1 1 d . . . . .
H18A H 0.595085 0.619773 0.973588 0.040 Uiso 1 1 calc R U . . .
H18B H 0.699859 0.811526 0.969632 0.040 Uiso 1 1 calc R U . . .
H18C H 0.765647 0.722724 1.037170 0.040 Uiso 1 1 calc R U . . .
O1S O 0.6776(6) 0.0819(5) 0.4731(4) 0.0697(13) Uani 0.5 1 d D . P B -1
C1S C 0.6044(17) -0.0356(19) 0.5332(10) 0.046(3) Uani 0.5 1 d D . P B -1
H1SA H 0.682638 -0.005502 0.586606 0.055 Uiso 0.5 1 calc R U P B -1
H1SB H 0.590149 -0.142423 0.507121 0.055 Uiso 0.5 1 calc R U P B -1
C2S C 0.4279(10) -0.0429(12) 0.5551(5) 0.057(2) Uani 0.5 1 d D . P B -1
H2SA H 0.432856 0.008966 0.614543 0.068 Uiso 0.5 1 calc R U P B -1
H2SB H 0.336038 -0.156365 0.551719 0.068 Uiso 0.5 1 calc R U P B -1
C3S C 0.3910(17) 0.0496(19) 0.4865(9) 0.041(3) Uani 0.5 1 d D . P B -1
H3SA H 0.404237 0.156651 0.511664 0.049 Uiso 0.5 1 calc R U P B -1
H3SB H 0.270664 -0.012038 0.459022 0.049 Uiso 0.5 1 calc R U P B -1
C4S C 0.5310(11) 0.0672(11) 0.4214(5) 0.0508(19) Uani 0.5 1 d D . P B -1
H4SA H 0.490253 -0.029084 0.378595 0.061 Uiso 0.5 1 calc R U P B -1
H4SB H 0.560911 0.164712 0.389546 0.061 Uiso 0.5 1 calc R U P B -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'
Br Br -0.2901 2.4595 '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'
Sn Sn -0.6537 1.4246 '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
C1 Sn1 C10 153.41(6) . . ?
C1 Sn1 C20 102.1(3) . . ?
C10 Sn1 C20 100.1(3) . . ?
C1 Sn1 C19 97.9(3) . . ?
C10 Sn1 C19 98.1(3) . . ?
C20 Sn1 C19 85.8(5) . . ?
C1 Sn1 N1 75.73(6) . . ?
C10 Sn1 N1 92.08(5) . . ?
C20 Sn1 N1 84.6(3) . . ?
C19 Sn1 N1 167.1(4) . . ?
C1 Sn1 Br2 99.74(6) . . ?
C10 Sn1 Br2 102.37(5) . . ?
N1 Sn1 Br2 83.90(4) . . ?
C1 Sn1 Br1 99.90(7) . . ?
C10 Sn1 Br1 96.36(7) . . ?
N1 Sn1 Br1 167.71(6) . . ?
Br2 Sn1 Br1 85.58(6) . . ?
N3 C19 Sn1 175.8(11) . . ?
N4 C20 Sn1 175.5(11) . . ?
C9 N1 C8 108.89(14) . . ?
C9 N1 C7 109.78(14) . . ?
C8 N1 C7 111.10(14) . . ?
C9 N1 Sn1 109.10(11) . . ?
C8 N1 Sn1 115.35(11) . . ?
C7 N1 Sn1 102.42(10) . . ?
C17 N2 C16 109.83(14) . . ?
C17 N2 C18 108.63(14) . . ?
C16 N2 C18 109.36(14) . . ?
C2 C1 C6 120.36(16) . . ?
C2 C1 Sn1 122.73(13) . . ?
C6 C1 Sn1 116.89(13) . . ?
C3 C2 C1 119.86(18) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 119.91(19) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.33(18) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 C6 120.59(18) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 118.93(17) . . ?
C5 C6 C7 121.35(17) . . ?
C1 C6 C7 119.61(16) . . ?
N1 C7 C6 111.02(14) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.76(16) . . ?
C15 C10 Sn1 121.02(12) . . ?
C11 C10 Sn1 118.92(12) . . ?
C12 C11 C10 120.16(17) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C13 C12 C11 120.09(18) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.05(17) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 120.68(17) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C10 C15 C14 119.24(16) . . ?
C10 C15 C16 121.52(15) . . ?
C14 C15 C16 119.17(16) . . ?
N2 C16 C15 112.72(14) . . ?
N2 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
N2 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S O1S C4S 104.4(8) . . ?
O1S C1S C2S 107.4(6) . . ?
O1S C1S H1SA 110.2 . . ?
C2S C1S H1SA 110.2 . . ?
O1S C1S H1SB 110.2 . . ?
C2S C1S H1SB 110.2 . . ?
H1SA C1S H1SB 108.5 . . ?
C1S C2S C3S 104.0(5) . . ?
C1S C2S H2SA 111.0 . . ?
C3S C2S H2SA 111.0 . . ?
C1S C2S H2SB 111.0 . . ?
C3S C2S H2SB 111.0 . . ?
H2SA C2S H2SB 109.0 . . ?
C2S C3S C4S 102.5(6) . . ?
C2S C3S H3SA 111.3 . . ?
C4S C3S H3SA 111.3 . . ?
C2S C3S H3SB 111.3 . . ?
C4S C3S H3SB 111.3 . . ?
H3SA C3S H3SB 109.2 . . ?
O1S C4S C3S 104.3(7) . . ?
O1S C4S H4SA 110.9 . . ?
C3S C4S H4SA 110.9 . . ?
O1S C4S H4SB 110.9 . . ?
C3S C4S H4SB 110.9 . . ?
H4SA C4S H4SB 108.9 . . ?
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
Sn1 C1 2.1162(17) . ?
Sn1 C10 2.1274(16) . ?
Sn1 C20 2.159(7) . ?
Sn1 C19 2.228(7) . ?
Sn1 N1 2.4818(14) . ?
Sn1 Br2 2.6188(10) . ?
Sn1 Br1 2.6619(14) . ?
N3 C19 1.157(7) . ?
C20 N4 1.130(7) . ?
N1 C9 1.474(2) . ?
N1 C8 1.475(2) . ?
N1 C7 1.482(2) . ?
N2 C17 1.474(2) . ?
N2 C16 1.474(2) . ?
N2 C18 1.477(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.394(2) . ?
C2 C3 1.389(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.513(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.388(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.389(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.399(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.513(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.408(8) . ?
O1S C4S 1.411(6) . ?
C1S C2S 1.500(8) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S C3S 1.515(9) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.516(8) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
