#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:09:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178803 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/57/4105782.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_4105782
loop_
_publ_author_name
'Aaron Sattler'
'Gerard Parkin'
_publ_section_title
;
 Carbon-Sulfur Bond Cleavage and Hydrodesulfurization of Thiophenes by
 Tungsten
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3748
_journal_page_last               3751
_journal_paper_doi               10.1021/ja111034g
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C20 H44 P4 S W'
_chemical_formula_weight         624.34
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.769(2)
_cell_angle_beta                 73.792(2)
_cell_angle_gamma                84.386(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9970(13)
_cell_length_b                   10.0679(15)
_cell_length_c                   15.782(2)
_cell_measurement_reflns_used    7851
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      2.36
_cell_volume                     1352.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0859
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21808
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    4.587
_exptl_absorpt_correction_T_max  0.9138
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.266
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         8217
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0434
_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)+(0.0220P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                6269
_reflns_number_total             8217
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja111034g_si_002_6.cif
_cod_data_source_block           wbtys10
_cod_database_code               4105782
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
W W -0.06111(2) 0.721950(19) 0.771683(13) 0.02093(6) Uani 1 1 d D . .
H1 H 0.013(5) 0.673(5) 0.858(2) 0.046(9) Uiso 1 1 d D A .
H2 H -0.106(6) 0.879(2) 0.729(3) 0.046(9) Uiso 1 1 d D A .
H3 H -0.2460(19) 0.748(5) 0.769(3) 0.046(9) Uiso 1 1 d D A .
P1 P -0.19381(15) 0.50842(13) 0.83478(10) 0.0352(3) Uani 1 1 d . A .
P2 P 0.15820(14) 0.86781(12) 0.73453(9) 0.0282(3) Uani 1 1 d . A .
P3 P -0.19932(15) 0.83468(13) 0.89641(8) 0.0296(3) Uani 1 1 d . A .
P4 P -0.10556(15) 0.72841(14) 0.62110(9) 0.0344(3) Uani 1 1 d . A .
C1 C 0.139(8) 0.572(8) 0.7276(12) 0.025(2) Uani 0.796(5) 1 d PD A 1
C2 C 0.2104(15) 0.5240(12) 0.6485(5) 0.0294(18) Uani 0.796(5) 1 d PD A 1
H2A H 0.1874 0.5639 0.5946 0.035 Uiso 0.796(5) 1 calc PR A 1
C3 C 0.3214(8) 0.4122(10) 0.6502(6) 0.026(2) Uani 0.796(5) 1 d PD A 1
C4 C 0.341(3) 0.373(2) 0.7368(7) 0.0265(13) Uani 0.796(5) 1 d PD A 1
S1 S 0.2133(2) 0.47386(18) 0.81030(11) 0.0294(5) Uani 0.796(5) 1 d PD A 1
C5 C 0.4456(8) 0.2699(10) 0.7545(6) 0.0295(17) Uani 0.796(5) 1 d PD A 1
H5A H 0.4594 0.2473 0.8127 0.035 Uiso 0.796(5) 1 calc PR A 1
C6 C 0.5307(13) 0.2003(11) 0.6861(5) 0.0297(19) Uani 0.796(5) 1 d PD A 1
H6A H 0.5962 0.1240 0.6985 0.036 Uiso 0.796(5) 1 calc PR A 1
C7 C 0.520(2) 0.2420(15) 0.5987(6) 0.037(2) Uani 0.796(5) 1 d PD A 1
H7A H 0.5858 0.1990 0.5513 0.044 Uiso 0.796(5) 1 calc PR A 1
C8 C 0.4164(12) 0.3447(14) 0.5811(7) 0.032(2) Uani 0.796(5) 1 d PD A 1
H8A H 0.4084 0.3705 0.5219 0.038 Uiso 0.796(5) 1 calc PR A 1
C1A C 0.13(3) 0.57(3) 0.726(4) 0.025(2) Uani 0.204(5) 1 d PD A 2
C2A C 0.213(3) 0.491(3) 0.7759(15) 0.0294(5) Uani 0.204(5) 1 d PD A 2
H2AA H 0.1983 0.4980 0.8370 0.035 Uiso 0.204(5) 1 calc PR A 2
C3A C 0.322(11) 0.392(8) 0.734(2) 0.0265(13) Uani 0.204(5) 1 d PD A 2
C4A C 0.354(4) 0.424(4) 0.640(2) 0.026(2) Uani 0.204(5) 1 d PD A 2
S1A S 0.2116(16) 0.5443(13) 0.6154(6) 0.0294(18) Uani 0.204(5) 1 d PD A 2
C5A C 0.450(6) 0.341(6) 0.583(2) 0.032(2) Uani 0.204(5) 1 d PD A 2
H5AA H 0.4642 0.3619 0.5206 0.038 Uiso 0.204(5) 1 calc PR A 2
C6A C 0.525(10) 0.228(6) 0.619(3) 0.037(2) Uani 0.204(5) 1 d PD A 2
H6AA H 0.5793 0.1627 0.5821 0.044 Uiso 0.204(5) 1 calc PR A 2
C7A C 0.518(6) 0.212(5) 0.709(3) 0.0297(19) Uani 0.204(5) 1 d PD A 2
H7AA H 0.5924 0.1532 0.7311 0.036 Uiso 0.204(5) 1 calc PR A 2
C8A C 0.405(4) 0.279(4) 0.767(2) 0.0295(17) Uani 0.204(5) 1 d PD A 2
H8AA H 0.3817 0.2490 0.8291 0.035 Uiso 0.204(5) 1 calc PR A 2
C11 C -0.1295(7) 0.3574(5) 0.7797(5) 0.0581(18) Uani 1 1 d . . .
H11A H -0.1872 0.2808 0.8157 0.087 Uiso 1 1 calc R A .
H11B H -0.0184 0.3377 0.7734 0.087 Uiso 1 1 calc R . .
H11C H -0.1486 0.3732 0.7206 0.087 Uiso 1 1 calc R . .
C12 C -0.1866(8) 0.4331(6) 0.9478(4) 0.0621(19) Uani 1 1 d . . .
H12A H -0.2367 0.4961 0.9899 0.093 Uiso 1 1 calc R A .
H12B H -0.0783 0.4138 0.9491 0.093 Uiso 1 1 calc R . .
H12C H -0.2409 0.3491 0.9646 0.093 Uiso 1 1 calc R . .
C13 C -0.4013(6) 0.5117(6) 0.8441(4) 0.0496(15) Uani 1 1 d . . .
H13A H -0.4181 0.5313 0.7845 0.074 Uiso 1 1 calc R A .
H13B H -0.4558 0.5818 0.8798 0.074 Uiso 1 1 calc R . .
H13C H -0.4412 0.4239 0.8730 0.074 Uiso 1 1 calc R . .
C21 C 0.1158(7) 1.0488(5) 0.7375(5) 0.069(2) Uani 1 1 d . . .
H21A H 0.0498 1.0637 0.7964 0.104 Uiso 1 1 calc R A .
H21B H 0.0621 1.0860 0.6920 0.104 Uiso 1 1 calc R . .
H21C H 0.2130 1.0935 0.7255 0.104 Uiso 1 1 calc R . .
C22 C 0.2915(6) 0.8315(6) 0.8045(4) 0.0495(15) Uani 1 1 d . . .
H22A H 0.3736 0.8956 0.7839 0.074 Uiso 1 1 calc R A .
H22B H 0.3375 0.7396 0.8008 0.074 Uiso 1 1 calc R . .
H22C H 0.2350 0.8398 0.8664 0.074 Uiso 1 1 calc R . .
C23 C 0.2979(7) 0.8760(7) 0.6250(4) 0.0561(17) Uani 1 1 d . . .
H23A H 0.3822 0.9322 0.6230 0.084 Uiso 1 1 calc R A .
H23B H 0.2461 0.9151 0.5791 0.084 Uiso 1 1 calc R . .
H23C H 0.3405 0.7849 0.6143 0.084 Uiso 1 1 calc R . .
C31 C -0.1011(8) 0.8709(9) 0.9747(5) 0.094(3) Uani 1 1 d . . .
H31A H -0.0105 0.9227 0.9427 0.141 Uiso 1 1 calc R A .
H31B H -0.0675 0.7862 1.0060 0.141 Uiso 1 1 calc R . .
H31C H -0.1720 0.9235 1.0180 0.141 Uiso 1 1 calc R . .
C32 C -0.2962(8) 0.9978(6) 0.8695(4) 0.069(2) Uani 1 1 d . . .
H32A H -0.3370 1.0404 0.9237 0.103 Uiso 1 1 calc R A .
H32B H -0.3818 0.9846 0.8451 0.103 Uiso 1 1 calc R . .
H32C H -0.2219 1.0558 0.8253 0.103 Uiso 1 1 calc R . .
C33 C -0.3718(8) 0.7653(7) 0.9774(4) 0.080(2) Uani 1 1 d . . .
H33A H -0.3429 0.6790 1.0090 0.120 Uiso 1 1 calc R A .
H33B H -0.4480 0.7513 0.9463 0.120 Uiso 1 1 calc R . .
H33C H -0.4168 0.8284 1.0202 0.120 Uiso 1 1 calc R . .
C41 C 0.0332(7) 0.7958(6) 0.5166(3) 0.0537(17) Uani 1 1 d . . .
H41A H -0.0084 0.7906 0.4662 0.081 Uiso 1 1 calc R A .
H41B H 0.1320 0.7426 0.5097 0.081 Uiso 1 1 calc R . .
H41C H 0.0497 0.8899 0.5184 0.081 Uiso 1 1 calc R . .
C42 C -0.2728(7) 0.8388(7) 0.6078(4) 0.0611(19) Uani 1 1 d . . .
H42A H -0.2865 0.8380 0.5485 0.092 Uiso 1 1 calc R A .
H42B H -0.2561 0.9308 0.6147 0.092 Uiso 1 1 calc R . .
H42C H -0.3658 0.8069 0.6533 0.092 Uiso 1 1 calc R . .
C43 C -0.1566(7) 0.5765(7) 0.5875(4) 0.0593(18) Uani 1 1 d . . .
H43A H -0.2544 0.5455 0.6284 0.089 Uiso 1 1 calc R A .
H43B H -0.0744 0.5056 0.5892 0.089 Uiso 1 1 calc R . .
H43C H -0.1684 0.5973 0.5268 0.089 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'
P P 0.1023 0.0942 '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'
W W -0.8490 6.8722 '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
H3 W H1 130(2)
H3 W H2 66(2)
H1 W H2 128(2)
H3 W C1A 136(10)
H1 W C1A 75(3)
H2 W C1A 133(8)
H3 W C1 137(3)
H1 W C1 73.2(17)
H2 W C1 133(2)
C1A W C1 2(8)
H3 W P3 72.1(16)
H1 W P3 69.4(16)
H2 W P3 73.8(16)
C1A W P3 144(2)
C1 W P3 142.5(7)
H3 W P2 133.8(16)
H1 W P2 78.8(16)
H2 W P2 67.6(17)
C1A W P2 81(10)
C1 W P2 80(3)
P3 W P2 92.48(4)
H3 W P1 71.8(16)
H1 W P1 79.9(16)
H2 W P1 138.1(17)
C1A W P1 80(10)
C1 W P1 80(3)
P3 W P1 93.50(5)
P2 W P1 154.16(4)
H3 W P4 64.9(16)
H1 W P4 159.3(16)
H2 W P4 68.7(16)
C1A W P4 85(3)
C1 W P4 86.3(7)
P3 W P4 131.13(4)
P2 W P4 100.80(5)
P1 W P4 94.06(5)
C13 P1 C11 99.3(3)
C13 P1 C12 101.7(3)
C11 P1 C12 98.0(3)
C13 P1 W 117.19(19)
C11 P1 W 119.9(2)
C12 P1 W 117.2(2)
C22 P2 C23 99.4(3)
C22 P2 C21 100.8(3)
C23 P2 C21 98.5(3)
C22 P2 W 116.42(19)
C23 P2 W 119.9(2)
C21 P2 W 118.1(2)
C31 P3 C32 102.1(4)
C31 P3 C33 97.8(4)
C32 P3 C33 94.6(3)
C31 P3 W 120.4(2)
C32 P3 W 116.0(2)
C33 P3 W 121.2(2)
C42 P4 C43 98.9(3)
C42 P4 C41 97.5(3)
C43 P4 C41 99.9(3)
C42 P4 W 112.05(19)
C43 P4 W 120.6(2)
C41 P4 W 123.1(2)
C2 C1 S1 107.3(7)
C2 C1 W 134.7(11)
S1 C1 W 117.6(5)
C1 C2 C3 117.7(8)
C8 C3 C4 117.6(7)
C8 C3 C2 131.0(8)
C4 C3 C2 111.2(7)
C5 C4 C3 121.9(8)
C5 C4 S1 129.1(7)
C3 C4 S1 109.0(6)
C1 S1 C4 94.7(5)
C4 C5 C6 119.1(8)
C5 C6 C7 120.2(8)
C8 C7 C6 120.5(9)
C7 C8 C3 120.5(7)
C2A C1A S1A 106.1(16)
C2A C1A W 128(2)
S1A C1A W 126.1(17)
C1A C2A C3A 119(3)
C8A C3A C4A 117(2)
C8A C3A C2A 133(2)
C4A C3A C2A 110(2)
C5A C4A C3A 122(2)
C5A C4A S1A 127(2)
C3A C4A S1A 108.4(19)
C1A S1A C4A 95.0(14)
C4A C5A C6A 119(2)
C5A C6A C7A 118(3)
C8A C7A C6A 121(3)
C7A C8A C3A 120(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W H3 1.672(10)
W H1 1.672(10)
W H2 1.673(10)
W C1A 2.20(2)
W C1 2.260(7)
W P3 2.4049(12)
W P2 2.4573(12)
W P1 2.4881(13)
W P4 2.5075(13)
P1 C13 1.829(5)
P1 C11 1.837(5)
P1 C12 1.839(6)
P2 C22 1.820(5)
P2 C23 1.826(5)
P2 C21 1.830(5)
P3 C31 1.805(6)
P3 C32 1.827(5)
P3 C33 1.829(6)
P4 C42 1.821(6)
P4 C43 1.835(6)
P4 C41 1.842(6)
C1 C2 1.373(15)
C1 S1 1.754(11)
C2 C3 1.432(12)
C3 C8 1.409(10)
C3 C4 1.414(9)
C4 C5 1.379(9)
C4 S1 1.762(8)
C5 C6 1.385(9)
C6 C7 1.402(8)
C7 C8 1.373(10)
C1A C2A 1.37(3)
C1A S1A 1.75(2)
C2A C3A 1.43(2)
C3A C8A 1.40(2)
C3A C4A 1.417(18)
C4A C5A 1.38(2)
C4A S1A 1.76(2)
C5A C6A 1.39(2)
C6A C7A 1.400(18)
C7A C8A 1.36(2)
