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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/1/56/74/1567433.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_1567433
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         'C12 H14 N2 S2 Si'
_chemical_formula_sum            'C12 H14 N2 S2 Si'
_chemical_formula_weight         278.46
_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                73.601(3)
_cell_angle_beta                 89.903(3)
_cell_angle_gamma                85.998(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7145(4)
_cell_length_b                   11.5896(5)
_cell_length_c                   12.9509(6)
_cell_measurement_reflns_used    67856
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.64
_cell_volume                     1395.13(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0181
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35958
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.690
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.8701
_exptl_absorpt_correction_T_min  0.7862
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   XShape
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       piece
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0293
_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)+(0.0398P)²+0.4395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6348
_reflns_number_total             6716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file
CIFs_all-in-one_SeidelWeigelEhrlichGerickeBrendlerWagler_pyOpyS-silanes.cif
_cod_data_source_block           ml003l01
_cod_database_code               1567433
_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   0.807
_shelx_estimated_absorpt_t_max   0.859
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 0.74777(4) 0.87099(3) 0.53200(3) 0.04586(10) Uani 1 1 d . . . . .
S2 S 1.03874(3) 0.88142(3) 0.63251(3) 0.04152(9) Uani 1 1 d . . . . .
Si1 Si 0.89306(3) 0.74517(3) 0.64269(3) 0.03050(8) Uani 1 1 d . . . . .
N1 N 0.62670(11) 0.66272(10) 0.59227(9) 0.0360(2) Uani 1 1 d . . . . .
N2 N 1.16717(10) 0.67614(10) 0.75298(8) 0.0320(2) Uani 1 1 d . . . . .
C1 C 0.60713(12) 0.77934(12) 0.53894(9) 0.0328(2) Uani 1 1 d . . . . .
C2 C 0.48277(13) 0.83320(13) 0.48786(10) 0.0367(3) Uani 1 1 d . . . . .
H2 H 0.4731 0.9167 0.4505 0.044 Uiso 1 1 calc R U . . .
C3 C 0.37411(13) 0.76069(14) 0.49349(11) 0.0401(3) Uani 1 1 d . . . . .
H3 H 0.2875 0.7941 0.4606 0.048 Uiso 1 1 calc R U . . .
C4 C 0.39261(14) 0.63931(14) 0.54726(11) 0.0413(3) Uani 1 1 d . . . . .
H4 H 0.3197 0.5878 0.5512 0.050 Uiso 1 1 calc R U . . .
C5 C 0.51952(14) 0.59452(13) 0.59517(11) 0.0392(3) Uani 1 1 d . . . . .
H5 H 0.5318 0.5110 0.6322 0.047 Uiso 1 1 calc R U . . .
C6 C 1.17837(12) 0.79422(11) 0.71090(9) 0.0305(2) Uani 1 1 d . . . . .
C7 C 1.29635(13) 0.85200(12) 0.72412(10) 0.0350(3) Uani 1 1 d . . . . .
H7 H 1.2996 0.9367 0.6946 0.042 Uiso 1 1 calc R U . . .
C8 C 1.40730(13) 0.78308(13) 0.78089(11) 0.0374(3) Uani 1 1 d . . . . .
H8 H 1.4890 0.8195 0.7909 0.045 Uiso 1 1 calc R U . . .
C9 C 1.39863(13) 0.65951(13) 0.82356(11) 0.0377(3) Uani 1 1 d . . . . .
H9 H 1.4743 0.6098 0.8623 0.045 Uiso 1 1 calc R U . . .
C10 C 1.27700(13) 0.61079(12) 0.80820(10) 0.0343(2) Uani 1 1 d . . . . .
H10 H 1.2707 0.5265 0.8383 0.041 Uiso 1 1 calc R U . . .
C11 C 0.82141(13) 0.69786(13) 0.78017(11) 0.0389(3) Uani 1 1 d . . . . .
H11A H 0.7720 0.6250 0.7885 0.058 Uiso 1 1 calc R U . . .
H11B H 0.7576 0.7626 0.7908 0.058 Uiso 1 1 calc R U . . .
H11C H 0.8969 0.6810 0.8336 0.058 Uiso 1 1 calc R U . . .
C12 C 0.96240(14) 0.62303(13) 0.58572(12) 0.0413(3) Uani 1 1 d . . . . .
H12A H 1.0009 0.5546 0.6440 0.062 Uiso 1 1 calc R U . . .
H12B H 1.0350 0.6531 0.5345 0.062 Uiso 1 1 calc R U . . .
H12C H 0.8879 0.5970 0.5486 0.062 Uiso 1 1 calc R U . . .
S3 S 0.47475(3) 0.93189(3) 0.16923(3) 0.04234(9) Uani 1 1 d . . . . .
S4 S 0.76726(4) 0.90062(3) 0.07031(3) 0.04742(10) Uani 1 1 d . . . . .
Si2 Si 0.61548(3) 0.78274(3) 0.15730(3) 0.02906(8) Uani 1 1 d . . . . .
N3 N 0.33929(11) 0.73342(10) 0.24277(9) 0.0341(2) Uani 1 1 d . . . . .
N4 N 0.88222(10) 0.67649(10) 0.10196(8) 0.0337(2) Uani 1 1 d . . . . .
C13 C 0.32718(12) 0.85336(11) 0.21844(10) 0.0325(2) Uani 1 1 d . . . . .
C14 C 0.20507(14) 0.91916(13) 0.23021(12) 0.0410(3) Uani 1 1 d . . . . .
H14 H 0.2004 1.0047 0.2122 0.049 Uiso 1 1 calc R U . . .
C15 C 0.09127(14) 0.85624(15) 0.26882(12) 0.0443(3) Uani 1 1 d . . . . .
H15 H 0.0068 0.8982 0.2783 0.053 Uiso 1 1 calc R U . . .
C16 C 0.10132(13) 0.73199(14) 0.29356(11) 0.0411(3) Uani 1 1 d . . . . .
H16 H 0.0241 0.6870 0.3196 0.049 Uiso 1 1 calc R U . . .
C17 C 0.22639(13) 0.67483(13) 0.27947(11) 0.0378(3) Uani 1 1 d . . . . .
H17 H 0.2332 0.5893 0.2966 0.045 Uiso 1 1 calc R U . . .
C18 C 0.89887(12) 0.79288(12) 0.05591(10) 0.0329(2) Uani 1 1 d . . . . .
C19 C 1.01641(14) 0.83375(12) -0.00185(11) 0.0381(3) Uani 1 1 d . . . . .
H19 H 1.0232 0.9171 -0.0363 0.046 Uiso 1 1 calc R U . . .
C20 C 1.12202(14) 0.75005(13) -0.00753(11) 0.0396(3) Uani 1 1 d . . . . .
H20 H 1.2039 0.7752 -0.0448 0.047 Uiso 1 1 calc R U . . .
C21 C 1.10747(14) 0.62910(13) 0.04165(11) 0.0394(3) Uani 1 1 d . . . . .
H21 H 1.1792 0.5698 0.0395 0.047 Uiso 1 1 calc R U . . .
C22 C 0.98585(14) 0.59675(12) 0.09411(10) 0.0367(3) Uani 1 1 d . . . . .
H22 H 0.9751 0.5135 0.1264 0.044 Uiso 1 1 calc R U . . .
C23 C 0.67945(13) 0.69262(12) 0.29304(10) 0.0364(3) Uani 1 1 d . . . . .
H23A H 0.6009 0.6690 0.3399 0.055 Uiso 1 1 calc R U . . .
H23B H 0.7376 0.7411 0.3235 0.055 Uiso 1 1 calc R U . . .
H23C H 0.7336 0.6202 0.2874 0.055 Uiso 1 1 calc R U . . .
C24 C 0.54517(14) 0.70080(14) 0.06748(12) 0.0432(3) Uani 1 1 d . . . . .
H24A H 0.6209 0.6715 0.0293 0.065 Uiso 1 1 calc R U . . .
H24B H 0.4802 0.7554 0.0152 0.065 Uiso 1 1 calc R U . . .
H24C H 0.4972 0.6322 0.1105 0.065 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 100.26(4) . . ?
C6 S2 Si1 101.00(4) . . ?
C11 Si1 C12 116.80(7) . . ?
C11 Si1 S2 110.29(5) . . ?
C12 Si1 S2 112.26(5) . . ?
C11 Si1 S1 110.82(5) . . ?
C12 Si1 S1 111.51(5) . . ?
S2 Si1 S1 92.601(18) . . ?
C1 N1 C5 117.02(11) . . ?
C6 N2 C10 117.27(10) . . ?
N1 C1 C2 123.78(12) . . ?
N1 C1 S1 117.96(9) . . ?
C2 C1 S1 118.25(10) . . ?
C3 C2 C1 117.69(13) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 119.49(12) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 118.48(12) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.53(13) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 C7 123.21(11) . . ?
N2 C6 S2 118.34(9) . . ?
C7 C6 S2 118.44(10) . . ?
C8 C7 C6 118.34(12) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C9 119.29(11) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 118.28(12) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N2 C10 C9 123.58(12) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
Si1 C11 H11A 109.5 . . ?
Si1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Si1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C12 H12A 109.5 . . ?
Si1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Si1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 S3 Si2 100.02(4) . . ?
C18 S4 Si2 100.56(4) . . ?
C24 Si2 C23 117.72(7) . . ?
C24 Si2 S3 111.69(5) . . ?
C23 Si2 S3 110.37(5) . . ?
C24 Si2 S4 108.91(5) . . ?
C23 Si2 S4 112.25(4) . . ?
S3 Si2 S4 93.262(18) . . ?
C13 N3 C17 117.15(11) . . ?
C18 N4 C22 117.38(11) . . ?
N3 C13 C14 123.34(12) . . ?
N3 C13 S3 117.68(9) . . ?
C14 C13 S3 118.97(10) . . ?
C15 C14 C13 118.07(13) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C16 C15 C14 119.49(13) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 118.28(12) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
N3 C17 C16 123.66(13) . . ?
N3 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
N4 C18 C19 123.01(12) . . ?
N4 C18 S4 118.37(9) . . ?
C19 C18 S4 118.61(10) . . ?
C20 C19 C18 118.37(12) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 119.29(12) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 118.29(13) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
N4 C22 C21 123.60(13) . . ?
N4 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
Si2 C23 H23A 109.5 . . ?
Si2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si2 C24 H24A 109.5 . . ?
Si2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
Si2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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 1.7752(13) . ?
S1 Si1 2.1708(5) . ?
S2 C6 1.7681(13) . ?
S2 Si1 2.1696(4) . ?
Si1 C11 1.8582(13) . ?
Si1 C12 1.8593(14) . ?
N1 C1 1.3331(17) . ?
N1 C5 1.3447(17) . ?
N2 C6 1.3346(16) . ?
N2 C10 1.3444(16) . ?
C1 C2 1.3968(17) . ?
C2 C3 1.3838(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3805(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.4014(16) . ?
C7 C8 1.3752(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3827(18) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
S3 C13 1.7724(13) . ?
S3 Si2 2.1682(5) . ?
S4 C18 1.7711(13) . ?
S4 Si2 2.1716(4) . ?
Si2 C24 1.8543(14) . ?
Si2 C23 1.8558(13) . ?
N3 C13 1.3323(16) . ?
N3 C17 1.3454(16) . ?
N4 C18 1.3331(16) . ?
N4 C22 1.3420(17) . ?
C13 C14 1.3967(17) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3797(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.4001(16) . ?
C19 C20 1.378(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3832(18) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
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 0.63(19) . . . . ?
C5 N1 C1 S1 -179.02(10) . . . . ?
Si1 S1 C1 N1 -8.27(10) . . . . ?
Si1 S1 C1 C2 172.06(9) . . . . ?
N1 C1 C2 C3 0.10(19) . . . . ?
S1 C1 C2 C3 179.75(10) . . . . ?
C1 C2 C3 C4 -0.86(19) . . . . ?
C2 C3 C4 C5 0.87(19) . . . . ?
C1 N1 C5 C4 -0.6(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
C10 N2 C6 C7 -1.66(17) . . . . ?
C10 N2 C6 S2 177.08(9) . . . . ?
Si1 S2 C6 N2 1.30(10) . . . . ?
Si1 S2 C6 C7 -179.90(9) . . . . ?
N2 C6 C7 C8 1.73(19) . . . . ?
S2 C6 C7 C8 -177.01(10) . . . . ?
C6 C7 C8 C9 -0.40(18) . . . . ?
C7 C8 C9 C10 -0.84(19) . . . . ?
C6 N2 C10 C9 0.31(18) . . . . ?
C8 C9 C10 N2 0.93(19) . . . . ?
C17 N3 C13 C14 0.61(19) . . . . ?
C17 N3 C13 S3 -179.63(9) . . . . ?
Si2 S3 C13 N3 5.11(10) . . . . ?
Si2 S3 C13 C14 -175.12(10) . . . . ?
N3 C13 C14 C15 -0.2(2) . . . . ?
S3 C13 C14 C15 -179.92(11) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C13 N3 C17 C16 -0.48(19) . . . . ?
C15 C16 C17 N3 -0.1(2) . . . . ?
C22 N4 C18 C19 1.91(19) . . . . ?
C22 N4 C18 S4 -177.12(9) . . . . ?
Si2 S4 C18 N4 -3.70(10) . . . . ?
Si2 S4 C18 C19 177.23(10) . . . . ?
N4 C18 C19 C20 -2.7(2) . . . . ?
S4 C18 C19 C20 176.29(10) . . . . ?
C18 C19 C20 C21 1.4(2) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C18 N4 C22 C21 0.24(19) . . . . ?
C20 C21 C22 N4 -1.5(2) . . . . ?
