#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:00:39 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178881 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/10/4111084.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_4111084
loop_
_publ_author_name
'Eric Block'
'Evgeny V. Dikarev'
'Richard S. Glass'
'Jin Jin'
'Bo Li'
'Xiaojie Li'
'Shao-Zhong Zhang'
_publ_section_title
;
 Synthesis, Structure, and Chemistry of New, Mixed Group 14 and 16
 Heterocycles: Nucleophile-Induced Ring Contraction of Mesocyclic
 Dications
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14949
_journal_page_last               14961
_journal_paper_doi               10.1021/ja065037j
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'Se2 (C H2)4 (Si (C H3)2)4'
_chemical_formula_sum            'C12 H32 Se2 Si4'
_chemical_formula_weight         446.66
_chemical_name_systematic
; 
 3,3,4,4,8,8,9,9-Octamethyl-1,6-diselena-3,4,8,9-tetrasilacyclodecane    
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.8910(10)
_cell_angle_beta                 94.1820(10)
_cell_angle_gamma                107.2310(10)
_cell_formula_units_Z            1
_cell_length_a                   6.2293(4)
_cell_length_b                   8.0571(5)
_cell_length_c                   11.4887(7)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.75
_cell_volume                     528.14(6)
_computing_cell_refinement       'SMART, SAINT'
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXP-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXCIF-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide ω exposures'
_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  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4677
_diffrn_reflns_theta_full        28.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         'none (area detector data)'
_exptl_absorpt_coefficient_mu    3.715
_exptl_absorpt_correction_T_max  0.8079
_exptl_absorpt_correction_T_min  0.5545
_exptl_absorpt_correction_type   'multi-scan (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       noref
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0504
_reflns_number_gt                2256
_reflns_number_total             2371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja065037jsi20060721_015610.cif
_cod_data_source_block           C12H32Se2Si4_42
_cod_database_code               4111084
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
Se1 Se 1.04158(2) 1.200126(18) 0.433048(12) 0.02606(6) Uani 1 1 d
Si1 Si 0.84396(7) 0.85592(5) 0.20666(3) 0.02345(9) Uani 1 1 d
Si2 Si 0.88026(7) 0.61985(5) 0.28434(3) 0.02341(9) Uani 1 1 d
C1 C 0.7691(3) 1.0287(2) 0.32451(15) 0.0294(3) Uani 1 1 d
C2 C 0.9025(3) 1.2844(2) 0.57314(14) 0.0280(3) Uani 1 1 d
C3 C 0.6107(3) 0.7659(2) 0.07223(15) 0.0346(4) Uani 1 1 d
C4 C 1.1160(3) 0.9681(2) 0.15623(16) 0.0343(3) Uani 1 1 d
C5 C 0.6016(3) 0.4868(2) 0.31821(17) 0.0345(3) Uani 1 1 d
C6 C 0.9812(3) 0.4633(2) 0.17007(16) 0.0350(4) Uani 1 1 d
H1A H 0.696(3) 1.089(3) 0.2798(19) 0.043(5) Uiso 1 1 d
H1B H 0.679(4) 0.974(3) 0.373(2) 0.051(6) Uiso 1 1 d
H2A H 0.838(3) 1.370(3) 0.5577(18) 0.044(5) Uiso 1 1 d
H2B H 0.783(4) 1.180(3) 0.5764(19) 0.049(6) Uiso 1 1 d
H3A H 0.647(4) 0.681(3) 0.011(2) 0.058(7) Uiso 1 1 d
H3B H 0.465(4) 0.709(4) 0.097(2) 0.065(7) Uiso 1 1 d
H3C H 0.596(4) 0.865(3) 0.039(2) 0.058(6) Uiso 1 1 d
H4A H 1.149(4) 0.886(3) 0.090(2) 0.053(6) Uiso 1 1 d
H4B H 1.119(4) 1.069(3) 0.132(2) 0.058(7) Uiso 1 1 d
H4C H 1.259(4) 1.011(3) 0.2223(19) 0.048(6) Uiso 1 1 d
H5A H 0.498(5) 0.432(3) 0.249(2) 0.065(7) Uiso 1 1 d
H5B H 0.531(4) 0.563(3) 0.373(2) 0.055(6) Uiso 1 1 d
H5C H 0.612(5) 0.398(4) 0.359(2) 0.071(7) Uiso 1 1 d
H6A H 0.877(4) 0.416(3) 0.093(2) 0.068(7) Uiso 1 1 d
H6B H 1.009(4) 0.366(3) 0.202(2) 0.060(7) Uiso 1 1 d
H6C H 1.122(5) 0.528(4) 0.149(2) 0.067(7) Uiso 1 1 d
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'
Se Se -0.0929 2.2259 '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
C1 Se1 C2 99.48(7) . .
C1 Se1 Si1 33.83(5) . .
C2 Se1 Si1 130.12(5) . .
C1 Se1 Si2 51.75(5) . .
C2 Se1 Si2 117.69(5) . .
Si1 Se1 Si2 31.681(9) . .
C4 Si1 C3 108.30(8) . .
C4 Si1 C1 109.46(8) . .
C3 Si1 C1 107.75(8) . .
C4 Si1 Si2 110.18(6) . .
C3 Si1 Si2 110.26(6) . .
C1 Si1 Si2 110.81(6) . .
C4 Si1 Se1 81.12(6) . .
C3 Si1 Se1 138.61(6) . .
C1 Si1 Se1 35.21(5) . .
Si2 Si1 Se1 103.211(17) . .
C6 Si2 C5 108.32(8) . .
C6 Si2 C2 108.44(8) . 2_776
C5 Si2 C2 109.75(8) . 2_776
C6 Si2 Si1 109.42(6) . .
C5 Si2 Si1 111.36(6) . .
C2 Si2 Si1 109.49(5) 2_776 .
C6 Si2 Se1 137.42(6) . .
C5 Si2 Se1 112.95(6) . .
C2 Si2 Se1 66.90(5) 2_776 .
Si1 Si2 Se1 45.109(12) . .
Si1 C1 Se1 110.96(8) . .
Si1 C1 H1A 105.7(13) . .
Se1 C1 H1A 111.0(12) . .
Si1 C1 H1B 110.5(15) . .
Se1 C1 H1B 105.9(14) . .
H1A C1 H1B 112.9(19) . .
Si2 C2 Se1 110.50(8) 2_776 .
Si2 C2 H2A 111.9(13) 2_776 .
Se1 C2 H2A 108.7(12) . .
Si2 C2 H2B 112.3(13) 2_776 .
Se1 C2 H2B 105.0(13) . .
H2A C2 H2B 108.3(18) . .
Si1 C3 H3A 109.1(15) . .
Si1 C3 H3B 109.9(14) . .
H3A C3 H3B 110(2) . .
Si1 C3 H3C 110.4(14) . .
H3A C3 H3C 108(2) . .
H3B C3 H3C 109(2) . .
Si1 C4 H4A 110.9(14) . .
Si1 C4 H4B 114.8(15) . .
H4A C4 H4B 107(2) . .
Si1 C4 H4C 114.0(11) . .
H4A C4 H4C 104.5(18) . .
H4B C4 H4C 104.3(18) . .
Si2 C5 H5A 111.0(16) . .
Si2 C5 H5B 112.9(13) . .
H5A C5 H5B 105(2) . .
Si2 C5 H5C 114.1(16) . .
H5A C5 H5C 109(2) . .
H5B C5 H5C 103.8(19) . .
Si2 C6 H6A 110.9(15) . .
Si2 C6 H6B 112.1(14) . .
H6A C6 H6B 112(2) . .
Si2 C6 H6C 110.4(16) . .
H6A C6 H6C 104(2) . .
H6B C6 H6C 107(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C1 1.9543(16) .
Se1 C2 1.9566(16) .
Se1 Si1 3.1652(4) .
Se1 Si2 4.3495(5) .
Si1 C4 1.8738(17) .
Si1 C3 1.8796(16) .
Si1 C1 1.8869(16) .
Si1 Si2 2.3464(6) .
Si2 C6 1.8722(17) .
Si2 C5 1.8736(17) .
Si2 C2 1.8865(16) 2_776
C1 H1A 0.96(2) .
C1 H1B 0.91(2) .
C2 Si2 1.8865(16) 2_776
C2 H2A 0.94(2) .
C2 H2B 0.95(2) .
C3 H3A 0.95(3) .
C3 H3B 0.98(3) .
C3 H3C 0.99(3) .
C4 H4A 0.95(3) .
C4 H4B 0.91(3) .
C4 H4C 1.04(2) .
C5 H5A 0.91(3) .
C5 H5B 0.99(2) .
C5 H5C 0.96(3) .
C6 H6A 0.98(3) .
C6 H6B 0.99(3) .
C6 H6C 0.96(3) .
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_4
C1 Se1 Si1 C4 143.74(11) . . .
C2 Se1 Si1 C4 173.23(8) . . .
Si2 Se1 Si1 C4 -108.78(6) . . .
C1 Se1 Si1 C3 36.07(13) . . .
C2 Se1 Si1 C3 65.57(11) . . .
Si2 Se1 Si1 C3 143.55(9) . . .
C2 Se1 Si1 C1 29.50(11) . . .
Si2 Se1 Si1 C1 107.48(9) . . .
C1 Se1 Si1 Si2 -107.48(9) . . .
C2 Se1 Si1 Si2 -77.98(6) . . .
C4 Si1 Si2 C6 -53.40(9) . . .
C3 Si1 Si2 C6 66.09(9) . . .
C1 Si1 Si2 C6 -174.70(8) . . .
Se1 Si1 Si2 C6 -138.66(7) . . .
C4 Si1 Si2 C5 -173.13(9) . . .
C3 Si1 Si2 C5 -53.64(9) . . .
C1 Si1 Si2 C5 65.57(8) . . .
Se1 Si1 Si2 C5 101.61(7) . . .
C4 Si1 Si2 C2 65.32(8) . . 2_776
C3 Si1 Si2 C2 -175.19(8) . . 2_776
C1 Si1 Si2 C2 -55.98(8) . . 2_776
Se1 Si1 Si2 C2 -19.94(6) . . 2_776
C4 Si1 Si2 Se1 85.26(6) . . .
C3 Si1 Si2 Se1 -155.25(7) . . .
C1 Si1 Si2 Se1 -36.04(5) . . .
C1 Se1 Si2 C6 109.56(11) . . .
C2 Se1 Si2 C6 -170.62(10) . . .
Si1 Se1 Si2 C6 67.02(9) . . .
C1 Se1 Si2 C5 -55.30(9) . . .
C2 Se1 Si2 C5 24.51(8) . . .
Si1 Se1 Si2 C5 -97.85(7) . . .
C1 Se1 Si2 C2 -157.91(8) . . 2_776
C2 Se1 Si2 C2 -78.10(8) . . 2_776
Si1 Se1 Si2 C2 159.54(6) . . 2_776
C1 Se1 Si2 Si1 42.54(6) . . .
C2 Se1 Si2 Si1 122.36(5) . . .
C4 Si1 C1 Se1 -38.30(11) . . .
C3 Si1 C1 Se1 -155.87(9) . . .
Si2 Si1 C1 Se1 83.42(8) . . .
C2 Se1 C1 Si1 -157.56(8) . . .
Si2 Se1 C1 Si1 -39.64(5) . . .
C1 Se1 C2 Si2 157.66(8) . . 2_776
Si1 Se1 C2 Si2 141.53(5) . . 2_776
Si2 Se1 C2 Si2 106.07(7) . . 2_776
Se1 C2 Si2 Si1 82.90(8) 2_776 2_776 .
