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#$Date: 2022-08-06 22:37:59 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/74/1567435.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_1567435
loop_
_publ_author_name
'Seidel, Anne'
'Weigel, Mareike'
'Ehrlich, Lisa'
'Gericke, Robert'
'Brendler, Erica'
'Wagler, Jörg'
_publ_section_title
;
 Molecular Structures of the Silicon Pyridine-2-(thi)olates Me3Si(pyX),
 Me2Si(pyX)2 and Ph2Si(pyX)2 (py = 2-Pyridyl, X = O, S), and Their Intra-
 and Intermolecular Ligand Exchange in Solution
;
_journal_issue                   8
_journal_name_full               Crystals
_journal_page_first              1054
_journal_paper_doi               10.3390/cryst12081054
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 N2 S2 Si'
_chemical_formula_sum            'C22 H18 N2 S2 Si'
_chemical_formula_weight         402.59
_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-2014/7
_cell_angle_alpha                96.698(6)
_cell_angle_beta                 114.442(6)
_cell_angle_gamma                90.107(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4763(8)
_cell_length_b                   10.2415(8)
_cell_length_c                   11.1044(8)
_cell_measurement_reflns_used    19701
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.67
_cell_volume                     972.92(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-2T'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14558
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.664
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XShape
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       piece
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0313
_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)+(0.0364P)²+0.4635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4149
_reflns_number_total             4698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file
CIFs_all-in-one_SeidelWeigelEhrlichGerickeBrendlerWagler_pyOpyS-silanes.cif
_cod_data_source_block           ml001filtr01
_cod_database_code               1567435
_shelx_shelxl_version_number     2014/7
_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   0.846
_shelx_estimated_absorpt_t_max   0.904
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
S1 S 0.39175(4) 0.73110(3) 0.54611(3) 0.02720(9) Uani 1 1 d . . . . .
S2 S 0.58594(4) 0.49866(3) 0.76046(4) 0.02950(9) Uani 1 1 d . . . . .
Si1 Si 0.62577(4) 0.72534(3) 0.77061(3) 0.02023(9) Uani 1 1 d . . . . .
N1 N 0.56179(12) 0.89978(10) 0.74284(11) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.45586(12) 0.69215(11) 0.82345(11) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.43912(15) 0.88962(13) 0.62065(13) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.37028(18) 1.00465(14) 0.57046(15) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.2837 0.9988 0.4863 0.038 Uiso 1 1 calc R U . . .
C3 C 0.42846(19) 1.12496(14) 0.64330(16) 0.0341(3) Uani 1 1 d . . . . .
H3 H 0.3827 1.2029 0.6095 0.041 Uiso 1 1 calc R U . . .
C4 C 0.55579(19) 1.13316(14) 0.76804(16) 0.0327(3) Uani 1 1 d . . . . .
H4 H 0.5968 1.2163 0.8192 0.039 Uiso 1 1 calc R U . . .
C5 C 0.62011(17) 1.01942(13) 0.81493(14) 0.0271(3) Uani 1 1 d . . . . .
H5 H 0.7067 1.0243 0.8990 0.033 Uiso 1 1 calc R U . . .
C6 C 0.45157(16) 0.55967(14) 0.81660(14) 0.0278(3) Uani 1 1 d . . . . .
C7 C 0.34507(19) 0.49328(16) 0.84871(17) 0.0378(3) Uani 1 1 d . . . . .
H7 H 0.3425 0.4001 0.8451 0.045 Uiso 1 1 calc R U . . .
C8 C 0.24421(19) 0.56588(19) 0.88561(17) 0.0422(4) Uani 1 1 d . . . . .
H8 H 0.1714 0.5227 0.9082 0.051 Uiso 1 1 calc R U . . .
C9 C 0.24818(18) 0.70247(18) 0.89012(16) 0.0373(3) Uani 1 1 d . . . . .
H9 H 0.1778 0.7528 0.9145 0.045 Uiso 1 1 calc R U . . .
C10 C 0.35610(16) 0.76325(15) 0.85850(14) 0.0293(3) Uani 1 1 d . . . . .
H10 H 0.3602 0.8563 0.8615 0.035 Uiso 1 1 calc R U . . .
C11 C 0.77616(15) 0.75561(13) 0.95257(13) 0.0238(2) Uani 1 1 d . . . . .
C12 C 0.74941(17) 0.82345(14) 1.05760(14) 0.0306(3) Uani 1 1 d . . . . .
H12 H 0.6527 0.8622 1.0386 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8608(2) 0.83569(18) 1.18928(16) 0.0413(4) Uani 1 1 d . . . . .
H13 H 0.8395 0.8822 1.2585 0.050 Uiso 1 1 calc R U . . .
C14 C 1.0025(2) 0.7798(2) 1.21884(16) 0.0463(4) Uani 1 1 d . . . . .
H14 H 1.0790 0.7888 1.3082 0.056 Uiso 1 1 calc R U . . .
C15 C 1.03199(18) 0.71108(19) 1.11771(17) 0.0424(4) Uani 1 1 d . . . . .
H15 H 1.1285 0.6718 1.1376 0.051 Uiso 1 1 calc R U . . .
C16 C 0.92012(16) 0.69945(15) 0.98668(15) 0.0313(3) Uani 1 1 d . . . . .
H16 H 0.9421 0.6519 0.9183 0.038 Uiso 1 1 calc R U . . .
C17 C 0.75651(15) 0.72021(13) 0.67699(13) 0.0238(2) Uani 1 1 d . . . . .
C18 C 0.86269(16) 0.82466(14) 0.69809(14) 0.0277(3) Uani 1 1 d . . . . .
H18 H 0.8690 0.9000 0.7591 0.033 Uiso 1 1 calc R U . . .
C19 C 0.95963(18) 0.82088(17) 0.63165(16) 0.0362(3) Uani 1 1 d . . . . .
H19 H 1.0296 0.8938 0.6466 0.043 Uiso 1 1 calc R U . . .
C20 C 0.95415(19) 0.71078(18) 0.54363(16) 0.0395(4) Uani 1 1 d . . . . .
H20 H 1.0211 0.7073 0.4992 0.047 Uiso 1 1 calc R U . . .
C21 C 0.8498(2) 0.60610(17) 0.52138(16) 0.0387(4) Uani 1 1 d . . . . .
H21 H 0.8450 0.5304 0.4613 0.046 Uiso 1 1 calc R U . . .
C22 C 0.75237(18) 0.61160(15) 0.58675(15) 0.0311(3) Uani 1 1 d . . . . .
H22 H 0.6808 0.5393 0.5696 0.037 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'
H H 0.0000 0.0000 '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'
S S 0.1246 0.1234 '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'
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 S1 Si1 73.15(5) . . ?
C6 S2 Si1 78.08(5) . . ?
N1 Si1 C17 96.55(5) . . ?
N1 Si1 C11 100.39(5) . . ?
C17 Si1 C11 101.37(6) . . ?
N1 Si1 N2 90.00(5) . . ?
C17 Si1 N2 163.44(6) . . ?
C11 Si1 N2 92.33(5) . . ?
N1 Si1 S2 154.73(4) . . ?
C17 Si1 S2 97.84(4) . . ?
C11 Si1 S2 97.00(4) . . ?
N2 Si1 S2 71.02(4) . . ?
N1 Si1 S1 67.93(4) . . ?
C17 Si1 S1 88.18(4) . . ?
C11 Si1 S1 165.91(5) . . ?
N2 Si1 S1 80.19(3) . . ?
S2 Si1 S1 91.868(18) . . ?
C5 N1 C1 120.93(11) . . ?
C5 N1 Si1 132.61(9) . . ?
C1 N1 Si1 106.32(8) . . ?
C10 N2 C6 120.99(12) . . ?
C10 N2 Si1 137.57(10) . . ?
C6 N2 Si1 101.44(9) . . ?
N1 C1 C2 119.29(12) . . ?
N1 C1 S1 112.59(9) . . ?
C2 C1 S1 128.10(11) . . ?
C3 C2 C1 119.77(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.96(13) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.06(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 120.98(13) . . ?
N1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N2 C6 C7 120.49(14) . . ?
N2 C6 S2 109.38(10) . . ?
C7 C6 S2 130.10(12) . . ?
C8 C7 C6 118.52(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 120.39(14) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.83(15) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C9 120.77(14) . . ?
N2 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C16 C11 C12 116.54(13) . . ?
C16 C11 Si1 118.70(11) . . ?
C12 C11 Si1 124.62(10) . . ?
C13 C12 C11 121.85(15) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 119.90(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.72(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.95(16) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 122.05(15) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C22 C17 C18 116.98(13) . . ?
C22 C17 Si1 121.80(11) . . ?
C18 C17 Si1 121.22(10) . . ?
C19 C18 C17 121.54(14) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 120.16(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.22(14) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.15(15) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.94(15) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
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
S1 C1 1.7026(14) . ?
S1 Si1 2.5683(5) . ?
S2 C6 1.7233(16) . ?
S2 Si1 2.3335(5) . ?
Si1 N1 1.9058(11) . ?
Si1 C17 1.9162(14) . ?
Si1 C11 1.9181(14) . ?
Si1 N2 1.9694(12) . ?
N1 C5 1.3602(17) . ?
N1 C1 1.3654(17) . ?
N2 C10 1.3477(18) . ?
N2 C6 1.3496(18) . ?
C1 C2 1.4069(18) . ?
C2 C3 1.368(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3716(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.400(2) . ?
C7 C8 1.375(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.4005(19) . ?
C11 C12 1.401(2) . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3965(19) . ?
C17 C18 1.3979(19) . ?
C18 C19 1.394(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
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
C5 N1 C1 C2 -1.47(19) . . . . ?
Si1 N1 C1 C2 -177.68(11) . . . . ?
C5 N1 C1 S1 177.34(10) . . . . ?
Si1 N1 C1 S1 1.12(11) . . . . ?
Si1 S1 C1 N1 -0.83(8) . . . . ?
Si1 S1 C1 C2 177.84(14) . . . . ?
N1 C1 C2 C3 1.1(2) . . . . ?
S1 C1 C2 C3 -177.48(12) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C1 N1 C5 C4 1.1(2) . . . . ?
Si1 N1 C5 C4 176.18(11) . . . . ?
C3 C4 C5 N1 -0.4(2) . . . . ?
C10 N2 C6 C7 -1.4(2) . . . . ?
Si1 N2 C6 C7 179.28(12) . . . . ?
C10 N2 C6 S2 176.71(10) . . . . ?
Si1 N2 C6 S2 -2.63(10) . . . . ?
Si1 S2 C6 N2 2.22(8) . . . . ?
Si1 S2 C6 C7 -179.93(15) . . . . ?
N2 C6 C7 C8 0.8(2) . . . . ?
S2 C6 C7 C8 -176.86(12) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C6 N2 C10 C9 0.9(2) . . . . ?
Si1 N2 C10 C9 179.93(11) . . . . ?
C8 C9 C10 N2 0.2(2) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
Si1 C11 C12 C13 176.26(12) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
Si1 C11 C16 C15 -176.51(12) . . . . ?
C22 C17 C18 C19 0.3(2) . . . . ?
Si1 C17 C18 C19 179.14(11) . . . . ?
C17 C18 C19 C20 -1.1(2) . . . . ?
C18 C19 C20 C21 1.0(2) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C17 -0.7(2) . . . . ?
C18 C17 C22 C21 0.6(2) . . . . ?
Si1 C17 C22 C21 -178.27(12) . . . . ?
