#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021850.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_4021850
loop_
_publ_author_name
'Yoshihiro Miyake'
'Mo Wu'
'M. Jalilur Rahman'
'Yoshiyuki Kuwatani'
'Masahiko Iyoda'
_publ_section_title
;
 Efficient Construction of Biaryls and Macrocyclic Cyclophanes via
 Electron-Transfer Oxidation of Lipshutz Cuprates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6110
_journal_page_last               6117
_journal_paper_doi               10.1021/jo0608063
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C20 H20 S4 Si2 '
_chemical_formula_sum            'C20 H20 S4 Si2'
_chemical_formula_weight         444.79
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             'Sat Jun 25 14:42:23 2005'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 113.257(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.190(3)
_cell_length_b                   11.435(1)
_cell_length_c                   14.976(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    153.2
_cell_measurement_theta_max      17.3
_cell_measurement_theta_min      15.0
_cell_volume                     4278.0(10)
_computing_cell_refinement       AFC
_computing_data_collection       AFC
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_publication_material  'teXsan Ver. 2.0'
_computing_structure_refinement  'teXsan Ver. 2.0'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5273
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.18
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1856.00
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.00
_refine_diff_density_min         0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4919
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          1.1959
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                3800
_reflns_number_total             5020
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0608063si20060420_034003.cif
_cod_original_sg_symbol_H-M      'C 2/c        '
_cod_original_formula_sum        'C20 H20 S4 Si2 '
_cod_database_code               4021850
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-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
S(1) S 0.63598(2) -0.13140(4) 0.16365(4) 0.0368(1) Uani 1.00 1 d
S(2) S 0.48252(2) 0.32572(5) 0.06521(4) 0.0395(2) Uani 1.00 1 d
S(3) S 0.75540(2) 0.07501(5) 0.08234(4) 0.0333(1) Uani 1.00 1 d
S(4) S 0.63318(2) 0.54815(4) 0.12574(4) 0.0391(1) Uani 1.00 1 d
Si(1) Si 0.59013(2) 0.19610(5) -0.06762(3) 0.0241(1) Uani 1.00 1 d
Si(2) Si 0.66797(2) 0.22042(4) 0.29062(4) 0.0237(1) Uani 1.00 1 d
C(1) C 0.64210(7) 0.0835(2) 0.2186(1) 0.0227(4) Uani 1.00 1 d
C(2) C 0.67002(8) -0.0199(2) 0.2388(1) 0.0296(5) Uani 1.00 1 d
C(3) C 0.58283(8) -0.0423(2) 0.1022(1) 0.0285(5) Uani 1.00 1 d
C(4) C 0.59131(7) 0.0692(2) 0.1373(1) 0.0226(4) Uani 1.00 1 d
C(5) C 0.55387(7) 0.1675(2) 0.0938(1) 0.0220(4) Uani 1.00 1 d
C(6) C 0.51865(8) 0.2097(2) 0.1303(1) 0.0302(5) Uani 1.00 1 d
C(7) C 0.51439(8) 0.3187(2) -0.0131(2) 0.0321(5) Uani 1.00 1 d
C(8) C 0.55150(7) 0.2311(2) 0.0085(1) 0.0234(4) Uani 1.00 1 d
C(9) C 0.66231(7) 0.1721(2) 0.0111(1) 0.0225(4) Uani 1.00 1 d
C(10) C 0.69045(7) 0.0778(2) 0.0000(1) 0.0282(5) Uani 1.00 1 d
C(11) C 0.74670(7) 0.2017(2) 0.1346(1) 0.0283(5) Uani 1.00 1 d
C(12) C 0.69578(7) 0.2440(2) 0.0910(1) 0.0220(4) Uani 1.00 1 d
C(13) C 0.67461(7) 0.3479(2) 0.1239(1) 0.0241(4) Uani 1.00 1 d
C(14) C 0.66334(8) 0.4519(2) 0.0758(2) 0.0327(5) Uani 1.00 1 d
C(15) C 0.63581(8) 0.4488(2) 0.2129(1) 0.0314(5) Uani 1.00 1 d
C(16) C 0.65894(7) 0.3453(2) 0.2055(1) 0.0243(4) Uani 1.00 1 d
C(17) C 0.63108(9) 0.2570(2) 0.3686(2) 0.0369(6) Uani 1.00 1 d
C(18) C 0.73989(8) 0.1991(2) 0.3711(1) 0.0346(5) Uani 1.00 1 d
C(19) C 0.56384(8) 0.0587(2) -0.1371(1) 0.0366(5) Uani 1.00 1 d
C(20) C 0.58200(9) 0.3194(2) -0.1542(2) 0.0406(6) Uani 1.00 1 d
H(1) H 0.7050 -0.0275 0.2892 0.0353 Uiso 1.00 1 calc
H(2) H 0.5505 -0.0669 0.0500 0.0345 Uiso 1.00 1 calc
H(3) H 0.5147 0.1778 0.1862 0.0350 Uiso 1.00 1 calc
H(4) H 0.5070 0.3712 -0.0670 0.0378 Uiso 1.00 1 calc
H(5) H 0.6753 0.0186 -0.0491 0.0334 Uiso 1.00 1 calc
H(6) H 0.7747 0.2392 0.1886 0.0330 Uiso 1.00 1 calc
H(7) H 0.6715 0.4687 0.0200 0.0392 Uiso 1.00 1 calc
H(8) H 0.6229 0.4650 0.2630 0.0371 Uiso 1.00 1 calc
H(9) H 0.5941 0.2683 0.3296 0.0435 Uiso 1.00 1 calc
H(10) H 0.6452 0.3267 0.4046 0.0435 Uiso 1.00 1 calc
H(11) H 0.6346 0.1948 0.4135 0.0435 Uiso 1.00 1 calc
H(12) H 0.7540 0.2686 0.4072 0.0413 Uiso 1.00 1 calc
H(13) H 0.7435 0.1365 0.4154 0.0413 Uiso 1.00 1 calc
H(14) H 0.7599 0.1807 0.3331 0.0413 Uiso 1.00 1 calc
H(15) H 0.5454 0.3298 -0.1956 0.0489 Uiso 1.00 1 calc
H(16) H 0.6019 0.3040 -0.1934 0.0489 Uiso 1.00 1 calc
H(17) H 0.5952 0.3906 -0.1192 0.0489 Uiso 1.00 1 calc
H(18) H 0.5269 0.0665 -0.1777 0.0437 Uiso 1.00 1 calc
H(19) H 0.5832 0.0396 -0.1760 0.0437 Uiso 1.00 1 calc
H(20) H 0.5677 -0.0051 -0.0928 0.0437 Uiso 1.00 1 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Si Si 0.082 0.070
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(2) 1.710(2) yes
S(1) C(3) 1.710(2) yes
S(2) C(6) 1.708(2) yes
S(2) C(7) 1.714(2) yes
S(3) C(10) 1.709(2) yes
S(3) C(11) 1.707(2) yes
S(4) C(14) 1.711(2) yes
S(4) C(15) 1.710(2) yes
Si(1) C(8) 1.874(2) yes
Si(1) C(9) 1.868(2) yes
Si(1) C(19) 1.865(2) yes
Si(1) C(20) 1.869(2) yes
Si(2) C(1) 1.874(2) yes
Si(2) C(16) 1.865(2) yes
Si(2) C(17) 1.864(2) yes
Si(2) C(18) 1.864(2) yes
C(1) C(2) 1.373(3) yes
C(1) C(4) 1.445(2) yes
C(2) H(1) 0.957 no
C(3) C(4) 1.362(3) yes
C(3) H(2) 0.960 no
C(4) C(5) 1.484(2) yes
C(5) C(6) 1.365(3) yes
C(5) C(8) 1.449(2) yes
C(6) H(3) 0.957 no
C(7) C(8) 1.367(3) yes
C(7) H(4) 0.961 no
C(9) C(10) 1.370(3) yes
C(9) C(12) 1.441(2) yes
C(10) H(5) 0.964 no
C(11) C(12) 1.365(3) yes
C(11) H(6) 0.964 no
C(12) C(13) 1.487(3) yes
C(13) C(14) 1.362(3) yes
C(13) C(16) 1.444(3) yes
C(14) H(7) 0.964 no
C(15) C(16) 1.366(3) yes
C(15) H(8) 0.964 no
C(17) H(9) 0.952 no
C(17) H(10) 0.954 no
C(17) H(11) 0.956 no
C(18) H(12) 0.952 no
C(18) H(13) 0.954 no
C(18) H(14) 0.953 no
C(19) H(18) 0.951 no
C(19) H(19) 0.951 no
C(19) H(20) 0.965 no
C(20) H(15) 0.950 no
C(20) H(16) 0.958 no
C(20) H(17) 0.958 no
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_publ_flag
S(1) C(2) C(1) Si(2) 178.19(10) yes
S(1) C(2) C(1) C(4) -0.9(2) yes
S(1) C(3) C(4) C(1) -1.5(2) yes
S(1) C(3) C(4) C(5) 175.5(1) yes
S(2) C(6) C(5) C(4) 178.3(1) yes
S(2) C(6) C(5) C(8) -0.4(2) yes
S(2) C(7) C(8) Si(1) 176.5(1) yes
S(2) C(7) C(8) C(5) -0.3(2) yes
S(3) C(10) C(9) Si(1) -179.01(10) yes
S(3) C(10) C(9) C(12) -0.2(2) yes
S(3) C(11) C(12) C(9) -0.7(2) yes
S(3) C(11) C(12) C(13) 175.5(1) yes
S(4) C(14) C(13) C(12) 173.6(1) yes
S(4) C(14) C(13) C(16) -0.7(2) yes
S(4) C(15) C(16) Si(2) 179.52(10) yes
S(4) C(15) C(16) C(13) -0.6(2) yes
Si(1) C(8) C(5) C(4) 5.0(2) yes
Si(1) C(8) C(5) C(6) -176.2(1) yes
Si(1) C(9) C(12) C(11) 179.3(1) yes
Si(1) C(9) C(12) C(13) 3.0(2) yes
Si(2) C(1) C(4) C(3) -177.5(1) yes
Si(2) C(1) C(4) C(5) 5.5(3) yes
Si(2) C(16) C(13) C(12) 6.3(2) yes
Si(2) C(16) C(13) C(14) -179.3(1) yes
C(1) Si(2) C(16) C(13) -49.6(2) yes
C(1) Si(2) C(16) C(15) 130.3(2) yes
C(1) C(2) S(1) C(3) 0.1(2) yes
C(1) C(4) C(5) C(6) -82.1(2) yes
C(1) C(4) C(5) C(8) 96.6(2) yes
C(2) S(1) C(3) C(4) 0.8(2) yes
C(2) C(1) Si(2) C(16) 133.3(2) yes
C(2) C(1) Si(2) C(17) -107.9(2) yes
C(2) C(1) Si(2) C(18) 11.6(2) yes
C(2) C(1) C(4) C(3) 1.6(2) yes
C(2) C(1) C(4) C(5) -175.5(2) yes
C(3) C(4) C(5) C(6) 101.2(2) yes
C(3) C(4) C(5) C(8) -80.1(2) yes
C(4) C(1) Si(2) C(16) -47.8(2) yes
C(4) C(1) Si(2) C(17) 71.0(2) yes
C(4) C(1) Si(2) C(18) -169.5(2) yes
C(4) C(5) C(8) C(7) -178.3(2) yes
C(5) C(6) S(2) C(7) 0.2(2) yes
C(5) C(8) Si(1) C(9) -48.1(2) yes
C(5) C(8) Si(1) C(19) 70.4(2) yes
C(5) C(8) Si(1) C(20) -169.9(2) yes
C(6) S(2) C(7) C(8) 0.0(2) yes
C(6) C(5) C(8) C(7) 0.5(2) yes
C(7) C(8) Si(1) C(9) 135.6(2) yes
C(7) C(8) Si(1) C(19) -105.9(2) yes
C(7) C(8) Si(1) C(20) 13.8(2) yes
C(8) Si(1) C(9) C(10) 132.1(2) yes
C(8) Si(1) C(9) C(12) -46.5(2) yes
C(9) C(10) S(3) C(11) -0.1(2) yes
C(9) C(12) C(13) C(14) -75.7(2) yes
C(9) C(12) C(13) C(16) 98.0(2) yes
C(10) S(3) C(11) C(12) 0.5(2) yes
C(10) C(9) Si(1) C(19) 12.3(2) yes
C(10) C(9) Si(1) C(20) -107.5(2) yes
C(10) C(9) C(12) C(11) 0.6(2) yes
C(10) C(9) C(12) C(13) -175.7(2) yes
C(11) C(12) C(13) C(14) 108.5(2) yes
C(11) C(12) C(13) C(16) -77.8(2) yes
C(12) C(9) Si(1) C(19) -166.2(2) yes
C(12) C(9) Si(1) C(20) 74.0(2) yes
C(12) C(13) C(16) C(15) -173.6(2) yes
C(13) C(14) S(4) C(15) 0.3(2) yes
C(13) C(16) Si(2) C(17) -171.3(2) yes
C(13) C(16) Si(2) C(18) 70.6(2) yes
C(14) S(4) C(15) C(16) 0.2(2) yes
C(14) C(13) C(16) C(15) 0.8(2) yes
C(15) C(16) Si(2) C(17) 8.6(2) yes
C(15) C(16) Si(2) C(18) -109.5(2) yes
C(15) C(16) Si(2) C(18) -109.5(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9949824
