#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/07/2220799.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_2220799
loop_
_publ_author_name
'Ng, Seik Weng'
_publ_section_title
;
 Low-temperature redetermination of tribenzylchloridotin(IV)
;
_journal_coeditor_code           HB2901
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m238
_journal_paper_doi               10.1107/S160053680900289X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Sn (C7 H7)3 Cl]'
_chemical_formula_moiety         'C21 H21 Cl Sn'
_chemical_formula_sum            'C21 H21 Cl Sn'
_chemical_formula_weight         427.52
_chemical_name_systematic
;
tribenzylchloridotin(IV)
;
_space_group_IT_number           146
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   16.7985(2)
_cell_length_b                   16.7985
_cell_length_c                   11.6875(2)
_cell_measurement_reflns_used    5172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.4
_cell_volume                     2856.23(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9077
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.479
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.253
_refine_ls_abs_structure_details 'Flack (1983), 1372 Fridel pairs'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                2431
_reflns_number_total             2737
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2901.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               2220799
_cod_database_fobs_code          2220799
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'
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_disorder_assembly
_atom_site_disorder_group
Sn Sn1 0.3333 0.6667 0.500000(15) 0.01587(10) Uani d S 1 . .
Sn Sn2 0.3333 0.6667 1.00289(2) 0.01945(10) Uani d S 1 . .
Cl Cl1 0.3333 0.6667 0.29532(14) 0.0388(4) Uani d S 1 . .
Cl Cl2 0.3333 0.6667 0.79730(13) 0.0364(4) Uani d S 1 . .
C C1 0.4692(2) 0.7751(2) 0.5415(3) 0.0231(6) Uani d . 1 . .
H H1A 0.4805 0.7730 0.6242 0.028 Uiso calc R 1 . .
H H1B 0.5149 0.7659 0.4988 0.028 Uiso calc R 1 . .
C C2 0.4812(2) 0.8672(2) 0.5120(3) 0.0214(6) Uani d . 1 . .
C C3 0.5272(2) 0.9129(2) 0.4134(3) 0.0353(7) Uani d . 1 . .
H H3 0.5524 0.8858 0.3646 0.042 Uiso calc R 1 . .
C C4 0.5369(3) 0.9971(2) 0.3847(3) 0.0475(9) Uani d . 1 . .
H H4 0.5686 1.0272 0.3167 0.057 Uiso calc R 1 . .
C C5 0.5008(3) 1.0378(2) 0.4544(4) 0.0438(8) Uani d . 1 . .
H H5 0.5070 1.0954 0.4344 0.053 Uiso calc R 1 . .
C C6 0.4552(2) 0.9929(2) 0.5546(4) 0.0361(8) Uani d . 1 . .
H H6 0.4305 1.0204 0.6034 0.043 Uiso calc R 1 . .
C C7 0.4456(2) 0.9089(2) 0.5831(3) 0.0283(7) Uani d . 1 . .
H H7 0.4146 0.8791 0.6516 0.034 Uiso calc R 1 . .
C C8 0.4652(2) 0.7841(2) 1.0378(3) 0.0269(7) Uani d . 1 . .
H H8A 0.4828 0.7815 1.1180 0.032 Uiso calc R 1 . .
H H8B 0.5119 0.7831 0.9871 0.032 Uiso calc R 1 . .
C C9 0.4632(2) 0.8710(2) 1.0191(3) 0.0259(6) Uani d . 1 . .
C C10 0.4869(2) 0.9179(2) 0.9159(3) 0.0417(8) Uani d . 1 . .
H H10 0.5076 0.8957 0.8546 0.050 Uiso calc R 1 . .
C C11 0.4811(3) 0.9968(2) 0.9002(4) 0.0531(10) Uani d . 1 . .
H H11 0.4966 1.0271 0.8281 0.064 Uiso calc R 1 . .
C C12 0.4528(2) 1.0317(2) 0.9886(4) 0.0482(9) Uani d . 1 . .
H H12 0.4500 1.0863 0.9784 0.058 Uiso calc R 1 . .
C C13 0.4288(2) 0.9860(2) 1.0914(4) 0.0401(8) Uani d . 1 . .
H H13 0.4091 1.0091 1.1527 0.048 Uiso calc R 1 . .
C C14 0.4331(2) 0.9067(2) 1.1065(3) 0.0311(7) Uani d . 1 . .
H H14 0.4151 0.8756 1.1779 0.037 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C1 Sn1 C1 2_665 . 115.06(6) ?
C1 Sn1 C1 2_665 3_565 115.06(7) ?
C1 Sn1 C1 . 3_565 115.06(6) ?
C1 Sn1 Cl1 2_665 . 103.05(9) ?
C1 Sn1 Cl1 . . 103.05(9) ?
C1 Sn1 Cl1 3_565 . 103.05(9) ?
C1 Sn1 Cl2 2_665 . 76.95(9) ?
C1 Sn1 Cl2 . . 76.95(9) ?
C1 Sn1 Cl2 3_565 . 76.95(9) ?
Cl1 Sn1 Cl2 . . 180.0 ?
C8 Sn2 C8 2_665 . 116.46(6) ?
C8 Sn2 C8 2_665 3_565 116.46(6) ?
C8 Sn2 C8 . 3_565 116.46(6) ?
C8 Sn2 Cl2 2_665 . 100.98(9) ?
C8 Sn2 Cl2 . . 100.98(9) ?
C8 Sn2 Cl2 3_565 . 100.98(9) ?
C8 Sn2 Cl1 2_665 1_556 79.02(9) ?
C8 Sn2 Cl1 . 1_556 79.02(9) ?
C8 Sn2 Cl1 3_565 1_556 79.02(9) ?
Cl2 Sn2 Cl1 . 1_556 180.0 ?
Sn2 Cl2 Sn1 . . 180.0 ?
C2 C1 Sn1 . . 111.2(2) ?
C2 C1 H1A . . 109.4 ?
Sn1 C1 H1A . . 109.4 ?
C2 C1 H1B . . 109.4 ?
Sn1 C1 H1B . . 109.4 ?
H1A C1 H1B . . 108.0 ?
C3 C2 C7 . . 118.4(3) ?
C3 C2 C1 . . 120.9(3) ?
C7 C2 C1 . . 120.7(3) ?
C4 C3 C2 . . 121.1(3) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 119.0(3) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C7 C6 C5 . . 120.5(3) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C2 . . 120.6(3) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
C9 C8 Sn2 . . 110.7(2) ?
C9 C8 H8A . . 109.5 ?
Sn2 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
Sn2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C10 C9 C14 . . 117.0(3) ?
C10 C9 C8 . . 122.9(3) ?
C14 C9 C8 . . 120.1(3) ?
C9 C10 C11 . . 121.4(3) ?
C9 C10 H10 . . 119.3 ?
C11 C10 H10 . . 119.3 ?
C12 C11 C10 . . 120.5(3) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 118.9(3) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C14 . . 120.6(3) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 121.6(3) ?
C13 C14 H14 . . 119.2 ?
C9 C14 H14 . . 119.2 ?
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
Sn1 C1 2_665 2.146(3) ?
Sn1 C1 . 2.146(3) y
Sn1 C1 3_565 2.146(3) ?
Sn1 Cl1 . 2.392(2) yes
Sn1 Cl2 . 3.475(2) n
Sn2 C8 2_665 2.143(3) ?
Sn2 C8 . 2.143(3) y
Sn2 C8 3_565 2.143(3) ?
Sn2 Cl2 . 2.403(2) yes
Sn2 Cl1 1_556 3.418(2) n
C1 C2 . 1.497(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.387(4) ?
C2 C7 . 1.398(4) ?
C3 C4 . 1.381(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.396(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.379(5) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.494(5) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.387(4) ?
C9 C14 . 1.400(4) ?
C10 C11 . 1.389(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.383(5) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.373(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.381(5) ?
C13 H13 . 0.9500 ?
C14 H14 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 Sn1 C1 C2 2_665 . . . -41.4(3) ?
C1 Sn1 C1 C2 3_565 . . . -178.70(16) ?
Cl1 Sn1 C1 C2 . . . . 69.9(2) ?
Cl2 Sn1 C1 C2 . . . . -110.1(2) ?
Sn1 C1 C2 C3 . . . . -101.4(3) ?
Sn1 C1 C2 C7 . . . . 78.1(3) ?
C7 C2 C3 C4 . . . . -0.7(5) ?
C1 C2 C3 C4 . . . . 178.8(3) ?
C2 C3 C4 C5 . . . . 0.0(5) ?
C3 C4 C5 C6 . . . . 0.6(6) ?
C4 C5 C6 C7 . . . . -0.5(5) ?
C5 C6 C7 C2 . . . . -0.2(5) ?
C3 C2 C7 C6 . . . . 0.8(5) ?
C1 C2 C7 C6 . . . . -178.7(3) ?
C8 Sn2 C8 C9 2_665 . . . -31.7(3) ?
C8 Sn2 C8 C9 3_565 . . . -175.18(15) ?
Cl2 Sn2 C8 C9 . . . . 76.6(2) ?
Cl1 Sn2 C8 C9 1_556 . . . -103.4(2) ?
Sn2 C8 C9 C10 . . . . -92.7(3) ?
Sn2 C8 C9 C14 . . . . 84.8(3) ?
C14 C9 C10 C11 . . . . 0.1(5) ?
C8 C9 C10 C11 . . . . 177.7(3) ?
C9 C10 C11 C12 . . . . 1.2(5) ?
C10 C11 C12 C13 . . . . -1.3(5) ?
C11 C12 C13 C14 . . . . 0.2(5) ?
C12 C13 C14 C9 . . . . 1.1(5) ?
C10 C9 C14 C13 . . . . -1.2(5) ?
C8 C9 C14 C13 . . . . -178.9(3) ?
