#------------------------------------------------------------------------------
#$Date: 2021-08-10 01:31:57 +0300 (Tue, 10 Aug 2021) $
#$Revision: 267999 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564335.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_1564335
loop_
_publ_author_name
'Xu, Yankun'
'Xu, Weiwei'
'Chen, Xinyang'
'Luo, Xiai'
'Lu, Haiyan'
'Zhang, Minghao'
'Yang, Xiumei'
'Deng, Guobo'
'Liang, Yun'
'Yang, Yuan'
_publ_section_title
;
 Me3SiSiMe2(OnBu): a disilane reagent for the synthesis of diverse
 silacycles via Brook- and retro-Brook-type rearrangement
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03487A
_journal_year                    2021
_chemical_formula_sum            'C24 H22 Cl N O Si'
_chemical_formula_weight         403.96
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                112.361(10)
_cell_angle_beta                 99.502(11)
_cell_angle_gamma                100.767(11)
_cell_formula_units_Z            2
_cell_length_a                   8.468(7)
_cell_length_b                   10.762(9)
_cell_length_c                   13.404(11)
_cell_measurement_reflns_used    2701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.54
_cell_volume                     1071.7(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7693
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.535
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0906P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2608
_reflns_number_total             3587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03487a2.cif
_cod_data_source_block           zxm343_0m
_cod_original_cell_volume        1071.6(15)
_cod_database_code               1564335
_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   0.938
_shelx_estimated_absorpt_t_max   0.954
_shelxl_version_number           2014-3
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
Cl1 Cl 0.03771(10) 0.27214(7) -0.39998(6) 0.0719(3) Uani 1 1 d . . . . .
N1 N 0.4468(2) 0.74499(18) -0.10568(16) 0.0411(5) Uani 1 1 d . . . . .
C7 C 0.5144(3) 0.7973(2) -0.1795(2) 0.0453(6) Uani 1 1 d . . . . .
H7A H 0.5806 0.8933 -0.1359 0.054 Uiso 1 1 calc R U . . .
H7B H 0.4229 0.7968 -0.2339 0.054 Uiso 1 1 calc R U . . .
Si1 Si 0.51058(9) 0.83562(7) 0.28423(6) 0.0493(3) Uani 1 1 d . . . . .
C3 C 0.8313(4) 0.5796(3) -0.3505(3) 0.0749(9) Uani 1 1 d . . . . .
H3 H 0.9032 0.5355 -0.3871 0.090 Uiso 1 1 calc R U . . .
C4 C 0.8454(4) 0.6102(3) -0.2390(3) 0.0744(9) Uani 1 1 d . . . . .
H4 H 0.9261 0.5851 -0.2005 0.089 Uiso 1 1 calc R U . . .
C5 C 0.7418(3) 0.6771(3) -0.1849(2) 0.0550(7) Uani 1 1 d . . . . .
H5 H 0.7532 0.6978 -0.1097 0.066 Uiso 1 1 calc R U . . .
C6 C 0.6204(3) 0.7142(2) -0.2405(2) 0.0403(6) Uani 1 1 d . . . . .
C14 C 0.3839(3) 0.7286(2) 0.05521(19) 0.0393(5) Uani 1 1 d . . . . .
C16 C 0.2757(3) 0.8187(2) 0.1130(2) 0.0377(5) Uani 1 1 d . . . . .
C21 C 0.3246(3) 0.8827(2) 0.2297(2) 0.0414(6) Uani 1 1 d . . . . .
C20 C 0.2322(3) 0.9689(2) 0.2848(2) 0.0511(7) Uani 1 1 d . . . . .
H20 H 0.2620 1.0127 0.3625 0.061 Uiso 1 1 calc R U . . .
C19 C 0.0980(3) 0.9900(3) 0.2262(3) 0.0550(7) Uani 1 1 d . . . . .
H19 H 0.0375 1.0471 0.2643 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7098(4) 0.6152(3) -0.4066(3) 0.0684(8) Uani 1 1 d . . . . .
H2 H 0.6985 0.5944 -0.4818 0.082 Uiso 1 1 calc R U . . .
C1 C 0.6054(3) 0.6812(3) -0.3523(2) 0.0541(7) Uani 1 1 d . . . . .
H1 H 0.5229 0.7041 -0.3913 0.065 Uiso 1 1 calc R U . . .
C13 C 0.2841(3) 0.6013(2) -0.05055(19) 0.0380(5) Uani 1 1 d . . . . .
C17 C 0.1419(3) 0.8412(2) 0.0537(2) 0.0472(6) Uani 1 1 d . . . . .
H17 H 0.1121 0.7994 -0.0240 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0535(3) 0.9266(3) 0.1116(3) 0.0538(7) Uani 1 1 d . . . . .
H18 H -0.0371 0.9412 0.0723 0.065 Uiso 1 1 calc R U . . .
C23 C 0.4813(4) 0.7635(3) 0.3880(3) 0.0778(9) Uani 1 1 d . . . . .
H23A H 0.3816 0.6876 0.3572 0.117 Uiso 1 1 calc R U . . .
H23B H 0.5750 0.7304 0.4058 0.117 Uiso 1 1 calc R U . . .
H23C H 0.4721 0.8354 0.4547 0.117 Uiso 1 1 calc R U . . .
C24 C 0.4930(3) 0.6970(3) 0.1422(2) 0.0520(7) Uani 1 1 d . . . . .
H24A H 0.6025 0.6985 0.1291 0.062 Uiso 1 1 calc R U . . .
H24B H 0.4421 0.6053 0.1370 0.062 Uiso 1 1 calc R U . . .
C22 C 0.7032(4) 0.9827(3) 0.3429(3) 0.0701(8) Uani 1 1 d . . . . .
H22A H 0.7176 1.0194 0.2889 0.105 Uiso 1 1 calc R U . . .
H22B H 0.6944 1.0549 0.4095 0.105 Uiso 1 1 calc R U . . .
H22C H 0.7973 0.9499 0.3606 0.105 Uiso 1 1 calc R U . . .
C15 C 0.4937(3) 0.8131(2) 0.0090(2) 0.0407(6) Uani 1 1 d . . . . .
O1 O 0.6047(2) 0.92037(17) 0.06297(14) 0.0538(5) Uani 1 1 d . . . . .
C8 C 0.3246(3) 0.6175(2) -0.14269(19) 0.0385(5) Uani 1 1 d . . . . .
C9 C 0.2529(3) 0.5186(2) -0.2503(2) 0.0443(6) Uani 1 1 d . . . . .
H9 H 0.2817 0.5303 -0.3109 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1344(3) 0.3992(2) -0.2647(2) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.0925(3) 0.3796(2) -0.1758(2) 0.0483(6) Uani 1 1 d . . . . .
H11 H 0.0141 0.2988 -0.1877 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1685(3) 0.4818(2) -0.0679(2) 0.0448(6) Uani 1 1 d . . . . .
H12 H 0.1411 0.4693 -0.0073 0.054 Uiso 1 1 calc R U . . .
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'
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C15 N1 C8 111.21(18) . . ?
C15 N1 C7 124.59(19) . . ?
C8 N1 C7 124.20(19) . . ?
N1 C7 C6 113.84(18) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C22 Si1 C23 109.93(15) . . ?
C22 Si1 C21 112.78(13) . . ?
C23 Si1 C21 113.40(14) . . ?
C22 Si1 C24 115.04(14) . . ?
C23 Si1 C24 112.88(15) . . ?
C21 Si1 C24 91.90(12) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 120.5(2) . . ?
C13 C14 C16 113.03(19) . . ?
C13 C14 C15 101.66(19) . . ?
C16 C14 C15 107.47(17) . . ?
C13 C14 C24 114.80(19) . . ?
C16 C14 C24 108.87(19) . . ?
C15 C14 C24 110.6(2) . . ?
C17 C16 C21 121.3(2) . . ?
C17 C16 C14 122.6(2) . . ?
C21 C16 C14 116.1(2) . . ?
C16 C21 C20 117.6(2) . . ?
C16 C21 Si1 111.08(17) . . ?
C20 C21 Si1 131.3(2) . . ?
C19 C20 C21 121.3(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C12 C13 C8 119.0(2) . . ?
C12 C13 C14 131.7(2) . . ?
C8 C13 C14 109.23(19) . . ?
C18 C17 C16 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C24 Si1 107.33(16) . . ?
C14 C24 H24A 110.2 . . ?
Si1 C24 H24A 110.2 . . ?
C14 C24 H24B 110.2 . . ?
Si1 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C15 N1 124.9(2) . . ?
O1 C15 C14 126.8(2) . . ?
N1 C15 C14 108.27(19) . . ?
C9 C8 C13 122.5(2) . . ?
C9 C8 N1 128.1(2) . . ?
C13 C8 N1 109.4(2) . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 Cl1 119.37(19) . . ?
C9 C10 Cl1 118.4(2) . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
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
Cl1 C10 1.742(3) . ?
N1 C15 1.375(3) . ?
N1 C8 1.408(3) . ?
N1 C7 1.454(3) . ?
C7 C6 1.503(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
Si1 C22 1.858(3) . ?
Si1 C23 1.861(3) . ?
Si1 C21 1.864(3) . ?
Si1 C24 1.880(3) . ?
C3 C2 1.372(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.379(4) . ?
C14 C13 1.514(3) . ?
C14 C16 1.541(3) . ?
C14 C15 1.543(3) . ?
C14 C24 1.547(3) . ?
C16 C17 1.387(3) . ?
C16 C21 1.397(3) . ?
C21 C20 1.399(3) . ?
C20 C19 1.377(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.373(4) . ?
C19 H19 0.9300 . ?
C2 C1 1.368(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C13 C12 1.377(3) . ?
C13 C8 1.397(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C15 O1 1.214(3) . ?
C8 C9 1.373(3) . ?
C9 C10 1.400(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C7 C6 111.1(2) . . . . ?
C8 N1 C7 C6 -68.8(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 -175.4(2) . . . . ?
N1 C7 C6 C5 -47.1(3) . . . . ?
N1 C7 C6 C1 137.1(2) . . . . ?
C13 C14 C16 C17 -38.0(3) . . . . ?
C15 C14 C16 C17 73.3(3) . . . . ?
C24 C14 C16 C17 -166.9(2) . . . . ?
C13 C14 C16 C21 144.9(2) . . . . ?
C15 C14 C16 C21 -103.8(2) . . . . ?
C24 C14 C16 C21 16.1(3) . . . . ?
C17 C16 C21 C20 0.9(3) . . . . ?
C14 C16 C21 C20 178.04(18) . . . . ?
C17 C16 C21 Si1 -178.54(17) . . . . ?
C14 C16 C21 Si1 -1.4(2) . . . . ?
C22 Si1 C21 C16 107.72(18) . . . . ?
C23 Si1 C21 C16 -126.52(19) . . . . ?
C24 Si1 C21 C16 -10.53(17) . . . . ?
C22 Si1 C21 C20 -71.7(2) . . . . ?
C23 Si1 C21 C20 54.1(3) . . . . ?
C24 Si1 C21 C20 170.1(2) . . . . ?
C16 C21 C20 C19 -0.1(3) . . . . ?
Si1 C21 C20 C19 179.30(18) . . . . ?
C21 C20 C19 C18 -0.4(4) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
C3 C2 C1 C6 0.5(4) . . . . ?
C5 C6 C1 C2 -1.0(4) . . . . ?
C7 C6 C1 C2 174.8(2) . . . . ?
C16 C14 C13 C12 -68.5(3) . . . . ?
C15 C14 C13 C12 176.6(2) . . . . ?
C24 C14 C13 C12 57.2(3) . . . . ?
C16 C14 C13 C8 111.4(2) . . . . ?
C15 C14 C13 C8 -3.5(2) . . . . ?
C24 C14 C13 C8 -122.9(2) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C14 C16 C17 C18 -178.2(2) . . . . ?
C20 C19 C18 C17 0.1(4) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C13 C14 C24 Si1 -150.22(17) . . . . ?
C16 C14 C24 Si1 -22.4(2) . . . . ?
C15 C14 C24 Si1 95.5(2) . . . . ?
C22 Si1 C24 C14 -97.4(2) . . . . ?
C23 Si1 C24 C14 135.37(19) . . . . ?
C21 Si1 C24 C14 18.92(17) . . . . ?
C8 N1 C15 O1 174.7(2) . . . . ?
C7 N1 C15 O1 -5.1(3) . . . . ?
C8 N1 C15 C14 -4.2(2) . . . . ?
C7 N1 C15 C14 175.87(19) . . . . ?
C13 C14 C15 O1 -174.3(2) . . . . ?
C16 C14 C15 O1 66.7(3) . . . . ?
C24 C14 C15 O1 -52.0(3) . . . . ?
C13 C14 C15 N1 4.6(2) . . . . ?
C16 C14 C15 N1 -114.3(2) . . . . ?
C24 C14 C15 N1 127.0(2) . . . . ?
C12 C13 C8 C9 0.2(3) . . . . ?
C14 C13 C8 C9 -179.7(2) . . . . ?
C12 C13 C8 N1 -178.85(19) . . . . ?
C14 C13 C8 N1 1.3(2) . . . . ?
C15 N1 C8 C9 -177.0(2) . . . . ?
C7 N1 C8 C9 2.9(4) . . . . ?
C15 N1 C8 C13 1.9(2) . . . . ?
C7 N1 C8 C13 -178.16(19) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
N1 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C9 C10 Cl1 178.97(17) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
Cl1 C10 C11 C12 -179.32(17) . . . . ?
C8 C13 C12 C11 -0.6(3) . . . . ?
C14 C13 C12 C11 179.3(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
