#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/35/2233517.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233517
loop_
_publ_author_name
'Ludwig, Gerd'
'Block, Michael'
'Wagner, Christoph'
'Steinborn, Dirk'
_publ_section_title
;
 [3-Methoxy-1-(phenylsulfanyl)propyl]triphenyltin(IV) benzene 0.17-solvate
;
_journal_coeditor_code           IS5011
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m149
_journal_paper_doi               10.1107/S1600536811055474
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Sn (C6 H5)3 (C10 H13 O S)], 0.17C6 H6'
_chemical_formula_moiety         'C28 H28 O S Sn, 0.17(C6 H6)'
_chemical_formula_sum            'C29 H29 O S Sn'
_chemical_formula_weight         544.27
_chemical_name_systematic
;
[3-Methoxy-1-(phenylsulfanyl)propyl]triphenyltin(IV) benzene 0.17-solvate
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   35.338(3)
_cell_length_b                   35.338(3)
_cell_length_c                   10.5660(8)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.0
_cell_volume                     11426.8(16)
_computing_cell_refinement       'IPDS EXPOSE (Stoe & Cie, 1999)'
_computing_data_collection       'IPDS EXPOSE (Stoe & Cie, 1999)'
_computing_data_reduction        'IPDS INTEGRATE (Stoe & Cie, 1999)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'area detector'
_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  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22832
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  0.8471
_exptl_absorpt_correction_T_min  0.6484
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(IPDS Software; Stoe & Cie, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4986
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.525
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.99
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0371P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0615
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                4008
_reflns_number_total             4905
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5011.cif
_cod_data_source_block           I
_cod_original_cell_volume        11427.1(16)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2233517
_cod_database_fobs_code          2233517
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.46298(8) 0.12671(8) 0.9677(2) 0.0295(5) Uani d . 1 1
H H1 0.4833 0.1173 0.9386 0.035 Uiso calc R 1 1
C C2 0.42345(9) 0.08653(9) 1.0248(3) 0.0421(7) Uani d . 1 1
H H3 0.4134 0.0627 0.9645 0.050 Uiso calc R 1 1
H H2 0.4330 0.0779 1.1000 0.050 Uiso calc R 1 1
C C3 0.38543(9) 0.09245(10) 1.0599(3) 0.0460(7) Uani d . 1 1
H H5 0.3647 0.0680 1.1110 0.055 Uiso calc R 1 1
H H4 0.3955 0.1191 1.1085 0.055 Uiso calc R 1 1
C C4 0.33026(10) 0.10298(12) 0.9689(4) 0.0637(9) Uani d . 1 1
H H6 0.3176 0.1040 0.8895 0.076 Uiso calc R 1 1
H H8 0.3412 0.1305 1.0117 0.076 Uiso calc R 1 1
H H7 0.3085 0.0801 1.0204 0.076 Uiso calc R 1 1
C C5 0.51631(8) 0.14921(9) 1.1889(2) 0.0326(6) Uani d . 1 1
C C6 0.51916(8) 0.11198(9) 1.1672(2) 0.0364(6) Uani d . 1 1
H H9 0.5065 0.0952 1.0951 0.044 Uiso calc R 1 1
C C7 0.54086(9) 0.09969(10) 1.2528(3) 0.0479(7) Uani d . 1 1
H H10 0.5426 0.0747 1.2378 0.057 Uiso calc R 1 1
C C8 0.55965(10) 0.12407(13) 1.3589(3) 0.0599(9) Uani d . 1 1
H H11 0.5745 0.1159 1.4153 0.072 Uiso calc R 1 1
C C9 0.55662(11) 0.16073(13) 1.3820(3) 0.0639(10) Uani d . 1 1
H H12 0.5693 0.1771 1.4546 0.077 Uiso calc R 1 1
C C10 0.53482(9) 0.17353(10) 1.2982(3) 0.0468(7) Uani d . 1 1
H H13 0.5326 0.1982 1.3149 0.056 Uiso calc R 1 1
C C11 0.51525(8) 0.20375(8) 0.7377(2) 0.0314(5) Uani d . 1 1
C C12 0.55158(9) 0.19985(9) 0.7660(3) 0.0414(6) Uani d . 1 1
H H14 0.5480 0.1765 0.8153 0.050 Uiso calc R 1 1
C C13 0.59285(10) 0.22978(10) 0.7227(3) 0.0519(8) Uani d . 1 1
H H15 0.6167 0.2264 0.7424 0.062 Uiso calc R 1 1
C C14 0.59838(10) 0.26436(11) 0.6508(3) 0.0576(9) Uani d . 1 1
H H16 0.6261 0.2847 0.6217 0.069 Uiso calc R 1 1
C C15 0.56311(11) 0.26918(11) 0.6216(4) 0.0666(10) Uani d . 1 1
H H17 0.5670 0.2928 0.5730 0.080 Uiso calc R 1 1
C C16 0.52209(9) 0.23920(9) 0.6638(3) 0.0486(8) Uani d . 1 1
H H18 0.4985 0.2427 0.6426 0.058 Uiso calc R 1 1
C C17 0.41851(8) 0.11558(8) 0.6483(2) 0.0272(5) Uani d . 1 1
C C18 0.38006(8) 0.07525(8) 0.6555(2) 0.0323(6) Uani d . 1 1
H H19 0.3660 0.0654 0.7330 0.039 Uiso calc R 1 1
C C19 0.36252(9) 0.04966(9) 0.5481(3) 0.0370(6) Uani d . 1 1
H H20 0.3370 0.0227 0.5544 0.044 Uiso calc R 1 1
C C20 0.38254(9) 0.06382(10) 0.4326(3) 0.0425(7) Uani d . 1 1
H H21 0.3706 0.0465 0.3611 0.051 Uiso calc R 1 1
C C21 0.42028(10) 0.10362(10) 0.4230(3) 0.0496(7) Uani d . 1 1
H H22 0.4337 0.1135 0.3448 0.060 Uiso calc R 1 1
C C22 0.43828(9) 0.12899(9) 0.5303(2) 0.0389(6) Uani d . 1 1
H H23 0.4642 0.1556 0.5232 0.047 Uiso calc R 1 1
C C23 0.41951(8) 0.19495(8) 0.8547(2) 0.0303(5) Uani d . 1 1
C C24 0.38656(9) 0.19384(9) 0.7791(3) 0.0392(6) Uani d . 1 1
H H24 0.3785 0.1775 0.7049 0.047 Uiso calc R 1 1
C C25 0.36561(9) 0.21676(10) 0.8130(3) 0.0488(8) Uani d . 1 1
H H25 0.3439 0.2158 0.7612 0.059 Uiso calc R 1 1
C C26 0.37677(10) 0.24078(10) 0.9222(3) 0.0515(8) Uani d . 1 1
H H26 0.3624 0.2557 0.9452 0.062 Uiso calc R 1 1
C C27 0.40953(11) 0.24266(10) 0.9980(3) 0.0515(8) Uani d . 1 1
H H27 0.4174 0.2590 1.0721 0.062 Uiso calc R 1 1
C C28 0.43065(9) 0.22026(9) 0.9638(3) 0.0411(6) Uani d . 1 1
H H28 0.4529 0.2222 1.0151 0.049 Uiso calc R 1 1
C C29 0.6516(4) 0.28958(16) 0.3333 0.240(8) Uani d D 1 1
H H29 0.6412 0.2597 0.3333 0.288 Uiso calc R 1 1
O O 0.36531(6) 0.09476(7) 0.94676(18) 0.0436(5) Uani d . 1 1
S S 0.49207(2) 0.16969(2) 1.08222(6) 0.03528(15) Uani d . 1 1
Sn Sn 0.450886(5) 0.158288(5) 0.805962(15) 0.02691(7) Uani d . 1 1
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'
O O 0.0106 0.0060 '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'
Sn Sn -0.6537 1.4246 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 S . . 112.78(18)
C2 C1 Sn . . 117.27(16)
S C1 Sn . . 105.52(11)
C2 C1 H1 . . 106.9
S C1 H1 . . 106.9
Sn C1 H1 . . 106.9
C3 C2 C1 . . 115.6(2)
C3 C2 H3 . . 108.4
C1 C2 H3 . . 108.4
C3 C2 H2 . . 108.4
C1 C2 H2 . . 108.4
H3 C2 H2 . . 107.5
O C3 C2 . . 108.0(2)
O C3 H5 . . 110.1
C2 C3 H5 . . 110.1
O C3 H4 . . 110.1
C2 C3 H4 . . 110.1
H5 C3 H4 . . 108.4
O C4 H6 . . 109.5
O C4 H8 . . 109.5
H6 C4 H8 . . 109.5
O C4 H7 . . 109.5
H6 C4 H7 . . 109.5
H8 C4 H7 . . 109.5
C6 C5 C10 . . 119.2(2)
C6 C5 S . . 124.04(19)
C10 C5 S . . 116.7(2)
C5 C6 C7 . . 120.1(3)
C5 C6 H9 . . 119.9
C7 C6 H9 . . 119.9
C8 C7 C6 . . 120.5(3)
C8 C7 H10 . . 119.7
C6 C7 H10 . . 119.7
C7 C8 C9 . . 119.8(3)
C7 C8 H11 . . 120.1
C9 C8 H11 . . 120.1
C8 C9 C10 . . 120.7(3)
C8 C9 H12 . . 119.6
C10 C9 H12 . . 119.6
C9 C10 C5 . . 119.6(3)
C9 C10 H13 . . 120.2
C5 C10 H13 . . 120.2
C12 C11 C16 . . 117.2(2)
C12 C11 Sn . . 122.56(19)
C16 C11 Sn . . 120.26(19)
C13 C12 C11 . . 121.8(3)
C13 C12 H14 . . 119.1
C11 C12 H14 . . 119.1
C14 C13 C12 . . 119.5(3)
C14 C13 H15 . . 120.3
C12 C13 H15 . . 120.3
C13 C14 C15 . . 120.2(3)
C13 C14 H16 . . 119.9
C15 C14 H16 . . 119.9
C16 C15 C14 . . 120.3(3)
C16 C15 H17 . . 119.9
C14 C15 H17 . . 119.9
C15 C16 C11 . . 121.2(3)
C15 C16 H18 . . 119.4
C11 C16 H18 . . 119.4
C22 C17 C18 . . 117.6(2)
C22 C17 Sn . . 117.01(17)
C18 C17 Sn . . 125.37(18)
C19 C18 C17 . . 120.7(2)
C19 C18 H19 . . 119.7
C17 C18 H19 . . 119.7
C20 C19 C18 . . 120.5(2)
C20 C19 H20 . . 119.7
C18 C19 H20 . . 119.7
C19 C20 C21 . . 119.8(2)
C19 C20 H21 . . 120.1
C21 C20 H21 . . 120.1
C20 C21 C22 . . 119.9(3)
C20 C21 H22 . . 120.1
C22 C21 H22 . . 120.1
C21 C22 C17 . . 121.5(3)
C21 C22 H23 . . 119.3
C17 C22 H23 . . 119.3
C28 C23 C24 . . 117.1(2)
C28 C23 Sn . . 121.46(18)
C24 C23 Sn . . 121.40(19)
C25 C24 C23 . . 121.1(3)
C25 C24 H24 . . 119.5
C23 C24 H24 . . 119.5
C26 C25 C24 . . 120.4(3)
C26 C25 H25 . . 119.8
C24 C25 H25 . . 119.8
C25 C26 C27 . . 119.5(3)
C25 C26 H26 . . 120.2
C27 C26 H26 . . 120.2
C28 C27 C26 . . 120.1(3)
C28 C27 H27 . . 120.0
C26 C27 H27 . . 120.0
C27 C28 C23 . . 121.7(3)
C27 C28 H28 . . 119.1
C23 C28 H28 . . 119.1
C29 C29 C29 17 18_545 120.0060(10)
C29 C29 H29 17 . 120.0
C29 C29 H29 18_545 . 120.0
C3 O C4 . . 112.7(2)
C5 S C1 . . 105.70(12)
C23 Sn C11 . . 107.59(9)
C23 Sn C17 . . 110.79(9)
C11 Sn C17 . . 104.90(9)
C23 Sn C1 . . 114.23(9)
C11 Sn C1 . . 103.82(9)
C17 Sn C1 . . 114.57(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.532(4) ?
C1 S . 1.807(2) ?
C1 Sn . 2.196(2) yes
C1 H1 . 0.9800 ?
C2 C3 . 1.506(4) ?
C2 H3 . 0.9700 ?
C2 H2 . 0.9700 ?
C3 O . 1.414(3) ?
C3 H5 . 0.9700 ?
C3 H4 . 0.9700 ?
C4 O . 1.426(4) ?
C4 H6 . 0.9600 ?
C4 H8 . 0.9600 ?
C4 H7 . 0.9600 ?
C5 C6 . 1.388(4) ?
C5 C10 . 1.391(4) ?
C5 S . 1.774(3) yes
C6 C7 . 1.389(4) ?
C6 H9 . 0.9300 ?
C7 C8 . 1.367(5) ?
C7 H10 . 0.9300 ?
C8 C9 . 1.374(5) ?
C8 H11 . 0.9300 ?
C9 C10 . 1.390(5) ?
C9 H12 . 0.9300 ?
C10 H13 . 0.9300 ?
C11 C12 . 1.391(4) ?
C11 C16 . 1.391(4) ?
C11 Sn . 2.150(2) yes
C12 C13 . 1.382(4) ?
C12 H14 . 0.9300 ?
C13 C14 . 1.368(4) ?
C13 H15 . 0.9300 ?
C14 C15 . 1.375(5) ?
C14 H16 . 0.9300 ?
C15 C16 . 1.374(4) ?
C15 H17 . 0.9300 ?
C16 H18 . 0.9300 ?
C17 C22 . 1.392(3) ?
C17 C18 . 1.395(3) ?
C17 Sn . 2.153(2) yes
C18 C19 . 1.389(4) ?
C18 H19 . 0.9300 ?
C19 C20 . 1.373(4) ?
C19 H20 . 0.9300 ?
C20 C21 . 1.375(4) ?
C20 H21 . 0.9300 ?
C21 C22 . 1.387(4) ?
C21 H22 . 0.9300 ?
C22 H23 . 0.9300 ?
C23 C28 . 1.390(4) ?
C23 C24 . 1.396(4) ?
C23 Sn . 2.147(2) yes
C24 C25 . 1.390(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.368(4) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.381(4) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.380(4) ?
C27 H27 . 0.9300 ?
C28 H28 . 0.9300 ?
C29 C29 17 1.360(5) ?
C29 C29 18_545 1.360(5) ?
C29 H29 . 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
S C1 C2 C3 70.6(3)
Sn C1 C2 C3 -52.3(3)
C1 C2 C3 O 71.8(3)
C10 C5 C6 C7 -1.0(4)
S C5 C6 C7 176.4(2)
C5 C6 C7 C8 -0.1(4)
C6 C7 C8 C9 0.8(5)
C7 C8 C9 C10 -0.4(5)
C8 C9 C10 C5 -0.7(5)
C6 C5 C10 C9 1.4(4)
S C5 C10 C9 -176.2(2)
C16 C11 C12 C13 -0.1(4)
Sn C11 C12 C13 -179.0(2)
C11 C12 C13 C14 0.4(5)
C12 C13 C14 C15 -0.2(6)
C13 C14 C15 C16 -0.3(6)
C14 C15 C16 C11 0.7(6)
C12 C11 C16 C15 -0.5(5)
Sn C11 C16 C15 178.5(3)
C22 C17 C18 C19 0.2(4)
Sn C17 C18 C19 -178.21(18)
C17 C18 C19 C20 -0.6(4)
C18 C19 C20 C21 0.1(4)
C19 C20 C21 C22 0.9(5)
C20 C21 C22 C17 -1.4(5)
C18 C17 C22 C21 0.8(4)
Sn C17 C22 C21 179.4(2)
C28 C23 C24 C25 -0.7(4)
Sn C23 C24 C25 178.3(2)
C23 C24 C25 C26 -0.4(5)
C24 C25 C26 C27 0.9(5)
C25 C26 C27 C28 -0.3(5)
C26 C27 C28 C23 -0.9(5)
C24 C23 C28 C27 1.4(4)
Sn C23 C28 C27 -177.6(2)
C2 C3 O C4 -176.5(2)
C6 C5 S C1 12.6(2)
C10 C5 S C1 -170.0(2)
C2 C1 S C5 68.1(2)
Sn C1 S C5 -162.64(11)
C28 C23 Sn C11 -74.8(2)
C24 C23 Sn C11 106.2(2)
C28 C23 Sn C17 171.1(2)
C24 C23 Sn C17 -7.9(2)
C28 C23 Sn C1 39.9(2)
C24 C23 Sn C1 -139.1(2)
C16 C11 Sn C23 -37.7(2)
C12 C11 Sn C23 141.3(2)
C16 C11 Sn C17 80.3(2)
C12 C11 Sn C17 -100.7(2)
C16 C11 Sn C1 -159.1(2)
C12 C11 Sn C1 19.8(2)
C22 C17 Sn C23 101.8(2)
C18 C17 Sn C23 -79.8(2)
C22 C17 Sn C11 -14.0(2)
C18 C17 Sn C11 164.4(2)
C22 C17 Sn C1 -127.14(19)
C18 C17 Sn C1 51.2(2)
C2 C1 Sn C23 73.5(2)
S C1 Sn C23 -52.99(14)
C2 C1 Sn C11 -169.59(19)
S C1 Sn C11 63.88(13)
C2 C1 Sn C17 -55.8(2)
S C1 Sn C17 177.69(10)
