#------------------------------------------------------------------------------
#$Date: 2019-11-26 16:41:09 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243652 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/94/4089469.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_4089469
loop_
_publ_author_name
'Durka, Krzysztof'
'Kliś, Tomasz'
'Serwatowski, Janusz'
'Woźniak, Krzysztof'
_publ_section_title
;
 Influence of the Silyl Group on the Reactivity of Some Ortho-Lithiated
 Aryl Alkyl Sulfides
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3145
_journal_paper_doi               10.1021/om400236x
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C15 H16 S2 Si'
_chemical_formula_sum            'C15 H16 S2 Si'
_chemical_formula_weight         288.51
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.74(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.465(11)
_cell_length_b                   7.6229(7)
_cell_length_c                   14.273(6)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1383
_cell_measurement_theta_min      1.9192
_cell_volume                     1443.9(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.1 (release 27-01-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,21:22:45)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.1 (release 27-01-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,21:22:45)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.1 (release 27-01-2011 CrysAlis171 .NET)
(compiled Feb 15 2011,21:22:45)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'KUMA CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.1395
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8057
_diffrn_reflns_theta_full        32.20
_diffrn_reflns_theta_max         32.20
_diffrn_reflns_theta_min         1.92
_diffrn_standards_interval_count '5o frames'
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unspecified
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1822
_reflns_number_gt                2793
_reflns_number_total             4577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400236x_si_001.cif
_cod_data_source_block           9
_cod_original_cell_volume        1443.8(13)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4089469
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.32687(6) 0.82354(10) 0.16106(6) 0.0163(2) Uani 1 1 d .
Si1 Si 0.48094(7) 1.20300(10) 0.14086(7) 0.0141(2) Uani 1 1 d .
S2 S 0.40715(6) 1.05933(10) 0.33212(6) 0.0182(2) Uani 1 1 d .
C1 C 0.2820(2) 1.0145(4) 0.0944(2) 0.0149(6) Uani 1 1 d .
C7 C 0.5486(2) 1.0191(4) 0.2149(2) 0.0125(6) Uani 1 1 d .
C10 C 0.6557(3) 0.7598(4) 0.3311(3) 0.0208(7) Uani 1 1 d .
H10 H 0.6923 0.6733 0.3706 0.025 Uiso 1 1 calc R
C6 C 0.1827(3) 1.0080(4) 0.0458(2) 0.0195(7) Uani 1 1 d .
H6 H 0.1423 0.9083 0.0528 0.023 Uiso 1 1 calc R
C8 C 0.5188(2) 0.9659(4) 0.3006(2) 0.0150(6) Uani 1 1 d .
C2 C 0.3447(2) 1.1612(4) 0.0862(2) 0.0147(6) Uani 1 1 d .
C12 C 0.6332(2) 0.9374(4) 0.1902(3) 0.0171(7) Uani 1 1 d .
H12 H 0.6551 0.9708 0.1329 0.021 Uiso 1 1 calc R
C3 C 0.2994(3) 1.2995(4) 0.0267(2) 0.0196(7) Uani 1 1 d .
H3 H 0.3379 1.4018 0.0200 0.023 Uiso 1 1 calc R
C15 C 0.4907(3) 1.4130(4) 0.2106(3) 0.0216(7) Uani 1 1 d .
H15A H 0.4559 1.5069 0.1711 0.032 Uiso 1 1 calc R
H15B H 0.5618 1.4442 0.2299 0.032 Uiso 1 1 calc R
H15C H 0.4594 1.3975 0.2673 0.032 Uiso 1 1 calc R
C14 C 0.5494(3) 1.2420(4) 0.0386(3) 0.0210(7) Uani 1 1 d .
H14A H 0.5172 1.3386 -0.0005 0.031 Uiso 1 1 calc R
H14B H 0.5470 1.1354 0.0000 0.031 Uiso 1 1 calc R
H14C H 0.6197 1.2724 0.0631 0.031 Uiso 1 1 calc R
C5 C 0.1422(3) 1.1452(5) -0.0128(3) 0.0250(8) Uani 1 1 d .
H5 H 0.0750 1.1394 -0.0462 0.030 Uiso 1 1 calc R
C13 C 0.3179(3) 0.8900(4) 0.2807(2) 0.0194(7) Uani 1 1 d .
H13A H 0.3280 0.7852 0.3221 0.023 Uiso 1 1 calc R
H13B H 0.2487 0.9336 0.2812 0.023 Uiso 1 1 calc R
C11 C 0.6864(3) 0.8090(4) 0.2466(3) 0.0198(7) Uani 1 1 d .
H11 H 0.7435 0.7551 0.2276 0.024 Uiso 1 1 calc R
C9 C 0.5715(2) 0.8375(4) 0.3573(2) 0.0185(7) Uani 1 1 d .
H9 H 0.5498 0.8026 0.4145 0.022 Uiso 1 1 calc R
C4 C 0.2015(3) 1.2900(5) -0.0214(3) 0.0236(8) Uani 1 1 d .
H4 H 0.1746 1.3846 -0.0611 0.028 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'
Si Si 0.0817 0.0704 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C13 101.79(15)
C14 Si1 C15 106.12(16)
C14 Si1 C7 107.31(15)
C15 Si1 C7 110.57(15)
C14 Si1 C2 105.96(17)
C15 Si1 C2 109.74(15)
C7 Si1 C2 116.51(14)
C8 S2 C13 98.10(16)
C6 C1 C2 121.3(3)
C6 C1 S1 116.4(2)
C2 C1 S1 122.3(2)
C12 C7 C8 117.1(3)
C12 C7 Si1 121.7(2)
C8 C7 Si1 121.0(2)
C9 C10 C11 119.7(3)
C9 C10 H10 120.1
C11 C10 H10 120.1
C5 C6 C1 121.0(3)
C5 C6 H6 119.5
C1 C6 H6 119.5
C9 C8 C7 121.1(3)
C9 C8 S2 120.2(3)
C7 C8 S2 118.6(2)
C1 C2 C3 115.6(3)
C1 C2 Si1 130.3(2)
C3 C2 Si1 114.1(2)
C11 C12 C7 122.1(3)
C11 C12 H12 118.9
C7 C12 H12 118.9
C4 C3 C2 122.3(3)
C4 C3 H3 118.9
C2 C3 H3 118.9
Si1 C15 H15A 109.5
Si1 C15 H15B 109.5
H15A C15 H15B 109.5
Si1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
Si1 C14 H14A 109.5
Si1 C14 H14B 109.5
H14A C14 H14B 109.5
Si1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C4 C5 C6 118.8(3)
C4 C5 H5 120.6
C6 C5 H5 120.6
S1 C13 S2 115.69(19)
S1 C13 H13A 108.4
S2 C13 H13A 108.4
S1 C13 H13B 108.4
S2 C13 H13B 108.4
H13A C13 H13B 107.4
C12 C11 C10 119.6(3)
C12 C11 H11 120.2
C10 C11 H11 120.2
C10 C9 C8 120.3(3)
C10 C9 H9 119.8
C8 C9 H9 119.8
C5 C4 C3 121.0(3)
C5 C4 H4 119.5
C3 C4 H4 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.787(3)
S1 C13 1.804(4)
Si1 C14 1.876(4)
Si1 C15 1.878(3)
Si1 C7 1.894(3)
Si1 C2 1.896(4)
S2 C8 1.789(4)
S2 C13 1.830(3)
C1 C6 1.399(5)
C1 C2 1.418(4)
C7 C12 1.395(4)
C7 C8 1.410(4)
C10 C9 1.386(5)
C10 C11 1.391(5)
C10 H10 0.9500
C6 C5 1.392(5)
C6 H6 0.9500
C8 C9 1.387(4)
C2 C3 1.424(4)
C12 C11 1.387(4)
C12 H12 0.9500
C3 C4 1.382(5)
C3 H3 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C5 C4 1.380(5)
C5 H5 0.9500
C13 H13A 0.9900
C13 H13B 0.9900
C11 H11 0.9500
C9 H9 0.9500
C4 H4 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
C13 S1 C1 C6 -101.7(3)
C13 S1 C1 C2 81.9(3)
C14 Si1 C7 C12 -0.2(3)
C15 Si1 C7 C12 -115.5(3)
C2 Si1 C7 C12 118.3(3)
C14 Si1 C7 C8 176.1(2)
C15 Si1 C7 C8 60.8(3)
C2 Si1 C7 C8 -65.4(3)
C2 C1 C6 C5 0.3(5)
S1 C1 C6 C5 -176.1(3)
C12 C7 C8 C9 -0.2(4)
Si1 C7 C8 C9 -176.7(2)
C12 C7 C8 S2 -177.0(2)
Si1 C7 C8 S2 6.6(3)
C13 S2 C8 C9 -83.4(3)
C13 S2 C8 C7 93.4(3)
C6 C1 C2 C3 0.7(5)
S1 C1 C2 C3 176.9(2)
C6 C1 C2 Si1 -178.5(2)
S1 C1 C2 Si1 -2.3(4)
C14 Si1 C2 C1 122.0(3)
C15 Si1 C2 C1 -123.8(3)
C7 Si1 C2 C1 2.8(4)
C14 Si1 C2 C3 -57.2(3)
C15 Si1 C2 C3 57.0(3)
C7 Si1 C2 C3 -176.4(2)
C8 C7 C12 C11 0.1(5)
Si1 C7 C12 C11 176.5(2)
C1 C2 C3 C4 -1.3(5)
Si1 C2 C3 C4 178.0(3)
C1 C6 C5 C4 -0.8(5)
C1 S1 C13 S2 -69.5(2)
C8 S2 C13 S1 -47.3(2)
C7 C12 C11 C10 -0.5(5)
C9 C10 C11 C12 1.0(5)
C11 C10 C9 C8 -1.1(5)
C7 C8 C9 C10 0.7(5)
S2 C8 C9 C10 177.4(3)
C6 C5 C4 C3 0.2(5)
C2 C3 C4 C5 0.9(5)
