#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2000500.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_2000500
loop_
_publ_author_name
'Watson, W. H.'
'Krawiec, M.'
'Ghosh, T.'
'Bartlett, P. D.'
_publ_contact_author
;
    William H. Watson
   Department of Chemistry, Texas Christian University,
         Fort Worth,  Texas 76129, USA
;
_publ_section_title
;
 <i>endo</i>-2-Phenyl-<i>exo</i>-3,4,5-trithiatricyclo[5.2.1.0^2,6^]decane
 <i>exo</i>-4-oxide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2092
_journal_page_last               2094
_journal_volume                  48
_journal_year                    1992
_chemical_formula_sum            'C13 H14 O S3'
_chemical_formula_weight         282.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           ' '
_cell_angle_alpha                90
_cell_angle_beta                 93.520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.232(3)
_cell_length_b                   5.9730(10)
_cell_length_c                   14.980(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      14.46
_cell_measurement_theta_min      11.57
_cell_volume                     1271.0(4)
_computing_cell_refinement       'Syntex  Diffractometer Control'
_computing_data_collection       'Syntex  Diffractometer Control'
_computing_data_reduction        'SHELXTL              '
_computing_publication_material  'SHELXTL             '
_computing_structure_refinement  'SHELXTL         '
_computing_structure_solution    'SHELXTL              '
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'R3M/\m update of Syntex P2~1~'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'x-ray tube'
_diffrn_radiation_type
;
MoK\a radiation, graphite monochromator
;
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.008
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            4103
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        <+-2
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.48
_exptl_crystal_description       prism
_exptl_crystal_F_000             592.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.35
_refine_ls_extinction_method
;
F~corr~ = F~c~/[1+2.6(2) x 10^-7^F~c~^2^/sin^2^ \q]^1/4^
;
_refine_ls_goodness_of_fit_obs   1.737
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           block-cascade
_refine_ls_number_constraints    0
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_obs          0.0346
_refine_ls_shift/esd_max         0.008
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = [\s^2^(F~o~) + 0.00014F~o~^2^]^-1^ '
_refine_ls_wR_factor_all         0.0394
_refine_ls_wR_factor_obs         0.0388
_reflns_number_observed          2551
_reflns_number_total             2922
_reflns_observed_criterion       'I >= 3\s(I)'
_[local]_cod_data_source_file    hh1012.cif
_[local]_cod_data_source_block   hh1012
_[local]_cod_cif_authors_sg_H-M  'P 21/n                 '
_cod_original_cell_volume        1270.8(3)
_cod_database_code               2000500
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0430(10) 0.0350(10) 0.0310(10) -0.0070(10) -0.0030(10) -0.0060(10)
S2 0.0440(10) 0.0450(10) 0.0230(10) -0.0110(10) -0.0040(10) 0.0030(10)
S3 0.0350(10) 0.0370(10) 0.0260(10) -0.0110(10) -0.0030(10) 0.002(2)
O1 0.0600(10) 0.0490(10) 0.0430(10) -0.0040(10) -0.0190(10) 0.0120(10)
C1 0.0360(10) 0.0400(10) 0.0320(10) 0.0090(10) 0.0020(10) -0.0050(10)
C2 0.0400(10) 0.0700(10) 0.0360(10) 0.0090(10) 0.0120(10) -0.0010(10)
C3 0.0430(10) 0.083(2) 0.0560(10) -0.0100(10) 0.0210(10) 0.0020(10)
C4 0.0250(10) 0.0690(10) 0.0440(10) -0.0050(10) 0.0010(10) -0.0030(10)
C5 0.0290(10) 0.0330(10) 0.0290(10) -0.0040(10) -0.0010(10) 0.0020(10)
C6 0.0270(10) 0.0300(10) 0.0240(10) 0.0010(10) 0.0020(10) 0.0000(10)
C7 0.0360(10) 0.0610(10) 0.0440(10) 0.0190(10) 0.0000(10) 0.0000(10)
C8 0.0260(10) 0.0320(10) 0.0250(10) 0.0000(10) 0.0030(10) 0.0020(10)
C9 0.0320(10) 0.0420(10) 0.0310(10) 0.0000(10) 0.0010(10) -0.0020(10)
C10 0.0320(10) 0.0660(10) 0.0320(10) -0.0050(10) -0.0040(10) 0.0020(10)
C11 0.0260(10) 0.0680(10) 0.0460(10) 0.0060(10) -0.0030(10) 0.0190(10)
C12 0.0340(10) 0.0430(10) 0.0550(10) 0.0100(10) 0.0070(10) 0.0100(10)
C13 0.0330(10) 0.0340(10) 0.0390(10) 0.0020(10) 0.0020(10) -0.0010(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
S1 -0.25370(10) 0.17740(10) 0.38500(10) 0.0360(10) Uani
S2 -0.20580(10) 0.48760(10) 0.34230(10) 0.0380(10) Uani
S3 -0.13720(10) 0.55690(10) 0.46660(10) 0.0330(10) Uani
O1 -0.28440(10) 0.6423(2) 0.32140(10) 0.0520(10) Uani
C1 -0.26950(10) 0.5517(3) 0.59810(10) 0.0360(10) Uani
C2 -0.3154(2) 0.4154(4) 0.67120(10) 0.0480(10) Uani
C3 -0.3874(2) 0.2665(5) 0.6180(2) 0.0600(10) Uani
C4 -0.37050(10) 0.3267(4) 0.52070(10) 0.0460(10) Uani
C5 -0.27290(10) 0.2297(3) 0.50150(10) 0.0310(10) Uani
C6 -0.20170(10) 0.3966(3) 0.54970(10) 0.0270(10) Uani
C7 -0.35140(10) 0.5769(4) 0.52790(10) 0.0470(10) Uani
C8 -0.12310(10) 0.2923(3) 0.60840(10) 0.0270(10) Uani
C9 -0.08220(10) 0.4078(3) 0.68140(10) 0.0350(10) Uani
C10 -0.00690(10) 0.3165(4) 0.73210(10) 0.0440(10) ?
C11 0.02870(10) 0.1117(4) 0.71080(10) 0.0470(10) ?
C12 -0.00990(10) -0.0028(4) 0.6382(2) 0.0440(10) ?
C13 -0.08520(10) 0.0862(3) 0.58700(10) 0.0350(10) ?
H1 -0.2390(10) 0.679(3) 0.6180(10) 0.035(5) Uani
H2A -0.272(2) 0.323(4) 0.707(2) 0.065(7) Uani
H2B -0.346(2) 0.509(4) 0.712(2) 0.058(7) Uani
H3A -0.378(2) 0.107(4) 0.625(2) 0.065(7) Uani
H3B -0.457(2) 0.304(4) 0.632(2) 0.085(8) Uani
H4 -0.4190(10) 0.283(3) 0.4750(10) 0.045(5) Uani
H5 -0.2630(10) 0.086(3) 0.5260(10) 0.032(5) Uani
H7A -0.336(2) 0.642(4) 0.4720(10) 0.047(6) Uani
H7B -0.406(2) 0.645(3) 0.5510(10) 0.057(6) Uani
H9 -0.1060(10) 0.552(4) 0.6930(10) 0.041(5) Uani
H10 0.0200(10) 0.404(4) 0.7810(10) 0.051(6) Uani
H11 0.075(2) 0.054(4) 0.741(2) 0.063(7) Uani
H12 0.0140(10) -0.146(4) 0.6240(10) 0.045(6) Uani
H13 -0.1080(10) 0.014(3) 0.5360(10) 0.041(5) ?
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables'
H 0.000 0.000 'International Tables'
O 0.008 0.006 'International Tables'
S 0.00? 0.00? 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
8 0 0
0 -1 -6
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
S2 S1 C5 102.30(10) yes
S1 S2 S3 92.70(10) yes
S1 S2 O1 111.40(10) yes
S3 S2 O1 111.90(10) yes
S2 S3 C6 105.80(10) yes
C2 C1 C6 108.6(2) yes
C2 C1 C7 101.7(2) yes
C6 C1 C7 102.00(10) yes
C1 C2 C3 103.6(2) yes
C2 C3 C4 102.6(2) yes
C3 C4 C5 106.5(2) yes
C3 C4 C7 101.6(2) yes
C5 C4 C7 102.8(2) yes
S1 C5 C4 115.70(10) yes
S1 C5 C6 115.00(10) yes
C4 C5 C6 103.80(10) yes
S3 C6 C1 110.70(10) yes
S3 C6 C5 110.60(10) yes
C1 C6 C5 101.10(10) yes
S3 C6 C8 102.90(10) yes
C1 C6 C8 115.70(10) yes
C5 C6 C8 116.10(10) yes
C1 C7 C4 94.5(2) yes
C6 C8 C9 120.70(10) yes
C6 C8 C13 121.00(10) yes
C9 C8 C13 118.1(2) yes
C8 C9 C10 120.5(2) yes
C9 C10 C11 120.5(2) yes
C10 C11 C12 119.6(2) yes
C11 C12 C13 120.5(2) yes
C8 C13 C12 120.7(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 S2 2.0880(10) yes
S1 C5 1.810(2) yes
S2 S3 2.0900(10) yes
S2 O1 1.470(2) yes
S3 C6 1.857(2) yes
C1 C2 1.542(3) yes
C1 C6 1.550(2) yes
C1 C7 1.528(3) yes
C2 C3 1.542(3) yes
C3 C4 1.534(3) yes
C4 C5 1.549(3) yes
C4 C7 1.522(3) yes
C5 C6 1.566(2) yes
C6 C8 1.513(2) yes
C8 C9 1.390(2) yes
C8 C13 1.389(2) yes
C9 C10 1.388(3) yes
C10 C11 1.369(3) yes
C11 C12 1.372(3) yes
C12 C13 1.385(3) yes