#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/64/4066498.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_4066498
loop_
_publ_author_name
'Wagler, Jörg'
'Heine, Thomas'
'Hill, Anthony F.'
_publ_section_title
;
 Poly(methimazolyl)silanes: Syntheses and Molecular Structures†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5607
_journal_paper_doi               10.1021/om1004989
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C7 H14 N2 S Si'
_chemical_formula_sum            'C7 H14 N2 S Si'
_chemical_formula_weight         186.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9036(6)
_cell_length_b                   7.0905(2)
_cell_length_c                   21.1015(9)
_cell_measurement_reflns_used    27779
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.032
_cell_measurement_theta_min      2.546
_cell_volume                     2080.26(14)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Scalepack
_computing_molecular_graphics    'ORTEP32 for windows (Farugia)'
_computing_publication_material  'Ciftab (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius Kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16935
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SORTAV
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.6232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                2966
_reflns_number_total             3838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1004989_si_002.cif
_cod_data_source_block           Me3Si(mt)
_cod_original_sg_symbol_Hall     -P2ac2n
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4066498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.86955(3) 0.2500 0.492018(19) 0.01966(10) Uani 1 2 d S
Si1 Si 0.66341(3) 0.2500 0.58308(2) 0.01797(10) Uani 1 2 d S
N1 N 0.78620(10) 0.2500 0.61015(6) 0.0165(3) Uani 1 2 d S
N2 N 0.94401(10) 0.2500 0.61129(6) 0.0176(3) Uani 1 2 d S
C1 C 0.86632(12) 0.2500 0.57232(7) 0.0159(3) Uani 1 2 d S
C2 C 1.04359(13) 0.2500 0.58993(9) 0.0243(4) Uani 1 2 d S
H2A H 1.0541 0.1433 0.5612 0.036 Uiso 0.50 1 calc PR
H2B H 1.0864 0.2386 0.6266 0.036 Uiso 0.50 1 calc PR
H2C H 1.0572 0.3681 0.5676 0.036 Uiso 0.50 1 calc PR
C3 C 0.81679(13) 0.2500 0.67318(8) 0.0196(3) Uani 1 2 d S
H3 H 0.7762 0.2500 0.7094 0.024 Uiso 1 2 calc SR
C4 C 0.91351(13) 0.2500 0.67388(8) 0.0205(3) Uani 1 2 d S
H4 H 0.9535 0.2500 0.7104 0.025 Uiso 1 2 calc SR
C5 C 0.64086(9) 0.03291(18) 0.53642(6) 0.0231(2) Uani 1 1 d .
H5A H 0.6848 0.0290 0.5001 0.035 Uiso 1 1 calc R
H5B H 0.5742 0.0329 0.5212 0.035 Uiso 1 1 calc R
H5C H 0.6517 -0.0779 0.5632 0.035 Uiso 1 1 calc R
C6 C 0.58993(13) 0.2500 0.65709(9) 0.0254(4) Uani 1 2 d S
H6A H 0.5217 0.2632 0.6462 0.038 Uiso 0.50 1 calc PR
H6B H 0.6096 0.3557 0.6841 0.038 Uiso 0.50 1 calc PR
H6C H 0.5998 0.1311 0.6799 0.038 Uiso 0.50 1 calc PR
S2 S 0.28783(3) 0.2500 0.31577(2) 0.02106(10) Uani 1 2 d S
Si2 Si 0.16191(3) 0.2500 0.17650(2) 0.01734(10) Uani 1 2 d S
N3 N 0.11346(10) 0.2500 0.25539(6) 0.0178(3) Uani 1 2 d S
N4 N 0.10316(10) 0.2500 0.35901(6) 0.0174(3) Uani 1 2 d S
C7 C 0.16685(11) 0.2500 0.31011(7) 0.0159(3) Uani 1 2 d S
C8 C 0.12902(13) 0.2500 0.42590(8) 0.0219(3) Uani 1 2 d S
H8A H 0.1402 0.3798 0.4400 0.033 Uiso 0.50 1 calc PR
H8B H 0.1877 0.1756 0.4320 0.033 Uiso 0.50 1 calc PR
H8C H 0.0765 0.1945 0.4507 0.033 Uiso 0.50 1 calc PR
C9 C 0.01037(12) 0.2500 0.33583(8) 0.0226(3) Uani 1 2 d S
H9 H -0.0470 0.2500 0.3603 0.027 Uiso 1 2 calc SR
C10 C 0.01598(12) 0.2500 0.27216(8) 0.0227(3) Uani 1 2 d S
H10 H -0.0369 0.2500 0.2436 0.027 Uiso 1 2 calc SR
C11 C 0.05372(15) 0.2500 0.12500(9) 0.0288(4) Uani 1 2 d S
H11A H 0.0123 0.1434 0.1363 0.043 Uiso 0.50 1 calc PR
H11B H 0.0734 0.2385 0.0806 0.043 Uiso 0.50 1 calc PR
H11C H 0.0183 0.3682 0.1309 0.043 Uiso 0.50 1 calc PR
C12 C 0.23330(11) 0.03291(19) 0.16388(6) 0.0294(3) Uani 1 1 d .
H12A H 0.2864 0.0289 0.1944 0.044 Uiso 1 1 calc R
H12B H 0.2593 0.0326 0.1207 0.044 Uiso 1 1 calc R
H12C H 0.1920 -0.0777 0.1698 0.044 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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Si1 C5 109.20(5) . .
N1 Si1 C5 109.20(5) . 8_565
C5 Si1 C5 112.25(8) . 8_565
N1 Si1 C6 104.69(8) . .
C5 Si1 C6 110.60(5) . .
C5 Si1 C6 110.60(5) 8_565 .
C1 N1 C3 107.89(14) . .
C1 N1 Si1 125.87(11) . .
C3 N1 Si1 126.24(12) . .
C1 N2 C4 109.49(14) . .
C1 N2 C2 124.68(14) . .
C4 N2 C2 125.83(14) . .
N2 C1 N1 107.09(13) . .
N2 C1 S1 125.77(12) . .
N1 C1 S1 127.14(12) . .
N2 C2 H2A 109.5 . .
N2 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N2 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 C3 N1 108.37(15) . .
C4 C3 H3 125.8 . .
N1 C3 H3 125.8 . .
C3 C4 N2 107.16(14) . .
C3 C4 H4 126.4 . .
N2 C4 H4 126.4 . .
Si1 C5 H5A 109.5 . .
Si1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
Si1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
Si1 C6 H6A 109.5 . .
Si1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
Si1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 Si2 C12 109.55(5) . 8_565
N3 Si2 C12 109.55(5) . .
C12 Si2 C12 112.54(10) 8_565 .
N3 Si2 C11 103.82(8) . .
C12 Si2 C11 110.52(6) 8_565 .
C12 Si2 C11 110.52(6) . .
C7 N3 C10 108.10(14) . .
C7 N3 Si2 125.24(11) . .
C10 N3 Si2 126.66(12) . .
C7 N4 C9 109.88(14) . .
C7 N4 C8 125.07(14) . .
C9 N4 C8 125.05(14) . .
N4 C7 N3 106.63(14) . .
N4 C7 S2 126.58(12) . .
N3 C7 S2 126.79(12) . .
N4 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 N4 107.44(15) . .
C10 C9 H9 126.3 . .
N4 C9 H9 126.3 . .
C9 C10 N3 107.96(15) . .
C9 C10 H10 126.0 . .
N3 C10 H10 126.0 . .
Si2 C11 H11A 109.5 . .
Si2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
Si2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
Si2 C12 H12A 109.5 . .
Si2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
Si2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.6950(16) .
Si1 N1 1.8002(15) .
Si1 C5 1.8540(13) .
Si1 C5 1.8539(13) 8_565
Si1 C6 1.8663(18) .
N1 C1 1.370(2) .
N1 C3 1.397(2) .
N2 C1 1.358(2) .
N2 C4 1.387(2) .
N2 C2 1.456(2) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 C4 1.345(2) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
S2 C7 1.6863(17) .
Si2 N3 1.7958(14) .
Si2 C12 1.8509(13) 8_565
Si2 C12 1.8509(13) .
Si2 C11 1.8556(19) .
N3 C7 1.373(2) .
N3 C10 1.401(2) .
N4 C7 1.360(2) .
N4 C9 1.380(2) .
N4 C8 1.457(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.346(2) .
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 .
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
C5 Si1 N1 C1 61.54(5) .
C5 Si1 N1 C1 -61.54(5) 8_565
C6 Si1 N1 C1 180.0 .
C5 Si1 N1 C3 -118.46(5) .
C5 Si1 N1 C3 118.46(5) 8_565
C6 Si1 N1 C3 0.0 .
C4 N2 C1 N1 0.0 .
C2 N2 C1 N1 180.0 .
C4 N2 C1 S1 180.0 .
C2 N2 C1 S1 0.0 .
C3 N1 C1 N2 0.0 .
Si1 N1 C1 N2 180.0 .
C3 N1 C1 S1 180.0 .
Si1 N1 C1 S1 0.0 .
C1 N1 C3 C4 0.0 .
Si1 N1 C3 C4 180.0 .
N1 C3 C4 N2 0.0 .
C1 N2 C4 C3 0.0 .
C2 N2 C4 C3 180.0 .
C12 Si2 N3 C7 -61.95(5) 8_565
C12 Si2 N3 C7 61.95(5) .
C11 Si2 N3 C7 180.0 .
C12 Si2 N3 C10 118.05(5) 8_565
C12 Si2 N3 C10 -118.05(5) .
C11 Si2 N3 C10 0.0 .
C9 N4 C7 N3 0.0 .
C8 N4 C7 N3 180.0 .
C9 N4 C7 S2 180.0 .
C8 N4 C7 S2 0.0 .
C10 N3 C7 N4 0.0 .
Si2 N3 C7 N4 180.0 .
C10 N3 C7 S2 180.0 .
Si2 N3 C7 S2 0.0 .
C7 N4 C9 C10 0.0 .
C8 N4 C9 C10 180.0 .
N4 C9 C10 N3 0.0 .
C7 N3 C10 C9 0.0 .
Si2 N3 C10 C9 180.0 .
