#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/29/2202944.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_2202944
loop_
_publ_author_name
'Gültekin, Zeynep'
'Adams, Harry'
'Hökelek, Tuncer'
_publ_section_title
(1RS,4RS)-1-Methoxyspiro[bicyclo[2.2.2]oct-5-ene-2,2'-[1',3']dithiolane]
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o926
_journal_page_last               o928
_journal_paper_doi               10.1107/S1600536803012005
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C11 H16 O S2'
_chemical_formula_sum            'C11 H16 O S2'
_chemical_formula_weight         228.36
_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                99.23(4)
_cell_angle_beta                 103.00(5)
_cell_angle_gamma                102.69(3)
_cell_formula_units_Z            2
_cell_length_a                   6.748(4)
_cell_length_b                   7.870(4)
_cell_length_c                   11.474(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      12
_cell_volume                     564.9(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'non-profiled 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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2493
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0545
_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)+(0.0676P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                1040
_reflns_number_total             1983
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6163.cif
_cod_data_source_block           I
_cod_database_code               2202944
_cod_database_fobs_code          2202944
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
H41 -0.307(9) 0.320(8) 0.268(5) 0.14(2) Uiso d . 1 . . H
H31 0.103(6) 0.526(4) 0.241(3) 0.063(10) Uiso d . 1 . . H
H61 -0.334(5) 0.734(4) 0.101(3) 0.054(9) Uiso d . 1 . . H
H62 -0.253(8) 0.582(7) 0.036(5) 0.120(16) Uiso d . 1 . . H
H51 -0.516(9) 0.458(7) 0.197(5) 0.128(18) Uiso d . 1 . . H
S1 0.14523(13) 0.75242(11) 0.10461(7) 0.0537(3) Uani d . 1 . . S
S2 -0.02942(15) 1.01505(11) 0.22952(10) 0.0674(4) Uani d . 1 . . S
O1 0.2272(3) 0.8104(3) 0.38379(19) 0.0608(6) Uani d . 1 . . O
C2 -0.0373(4) 0.7751(3) 0.1983(2) 0.0386(6) Uani d . 1 . . C
C1 0.0184(4) 0.7118(3) 0.3202(2) 0.0408(6) Uani d . 1 . . C
C4 -0.2288(6) 0.4076(5) 0.2180(4) 0.0676(10) Uani d . 1 . . C
C11 -0.3429(5) 0.6548(5) 0.3202(3) 0.0655(9) Uani d . 1 . . C
H11A -0.4261 0.7395 0.3068 0.079 Uiso calc R 1 . . H
H11B -0.4031 0.5800 0.3697 0.079 Uiso calc R 1 . . H
C3 -0.0032(5) 0.5118(4) 0.2862(3) 0.0552(8) Uani d . 1 . . C
C5 -0.3623(5) 0.5404(5) 0.1995(3) 0.0597(9) Uani d . 1 . . C
C6 -0.2620(5) 0.6598(5) 0.1219(3) 0.0588(9) Uani d . 1 . . C
C7 0.3251(6) 0.9731(5) 0.1657(4) 0.0767(11) Uani d . 1 . . C
H7A 0.4237 0.9746 0.2420 0.092 Uiso calc R 1 . . H
H7B 0.4048 1.0042 0.1081 0.092 Uiso calc R 1 . . H
C9 0.2998(6) 0.7914(5) 0.5060(3) 0.0674(10) Uani d . 1 . . C
H9A 0.4429 0.8625 0.5407 0.101 Uiso calc R 1 . . H
H9B 0.2935 0.6683 0.5057 0.101 Uiso calc R 1 . . H
H9C 0.2122 0.8306 0.5541 0.101 Uiso calc R 1 . . H
C8 0.2045(6) 1.1028(5) 0.1873(5) 0.0822(12) Uani d . 1 . . C
H8A 0.1663 1.1467 0.1133 0.099 Uiso calc R 1 . . H
H8B 0.2939 1.2035 0.2518 0.099 Uiso calc R 1 . . H
C10 -0.1484(4) 0.7441(4) 0.3825(3) 0.0508(7) Uani d . 1 . . C
H10A -0.1179 0.7120 0.4615 0.061 Uiso calc R 1 . . H
H10B -0.1399 0.8707 0.3974 0.061 Uiso calc R 1 . . H
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'
O O 0.0106 0.0060 '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'
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
C7 S1 C2 97.42(16) yes
C8 S2 C2 99.37(16) yes
C1 O1 C9 116.0(2) yes
C1 C2 C6 108.0(2) ?
C1 C2 S1 113.79(18) yes
C6 C2 S1 108.1(2) yes
C1 C2 S2 110.58(17) yes
C6 C2 S2 110.6(2) yes
S1 C2 S2 105.72(15) yes
O1 C1 C10 115.5(2) yes
O1 C1 C3 112.3(2) yes
C10 C1 C3 109.7(2) ?
O1 C1 C2 106.8(2) yes
C10 C1 C2 104.8(2) ?
C3 C1 C2 107.1(2) yes
C3 C4 C5 108.5(3) ?
C3 C4 H41 114(3) ?
C5 C4 H41 104(3) ?
C10 C11 C5 114.9(3) yes
C10 C11 H11A 108.6 ?
C5 C11 H11A 108.6 ?
C10 C11 H11B 108.6 ?
C5 C11 H11B 108.6 ?
H11A C11 H11B 107.5 ?
C4 C3 C1 111.7(3) yes
C4 C3 H31 119(2) ?
C1 C3 H31 93.6(19) ?
C11 C5 C4 109.6(3) ?
C11 C5 C6 108.3(3) ?
C4 C5 C6 105.3(3) yes
C11 C5 H51 92(3) ?
C4 C5 H51 100(3) ?
C6 C5 H51 139(3) ?
C5 C6 C2 109.8(3) ?
C5 C6 H61 112(2) ?
C2 C6 H61 106(2) ?
C5 C6 H62 112(3) ?
C2 C6 H62 110(3) ?
H61 C6 H62 106(4) ?
C8 C7 S1 109.3(3) yes
C8 C7 H7A 109.8 ?
S1 C7 H7A 109.8 ?
C8 C7 H7B 109.8 ?
S1 C7 H7B 109.8 ?
H7A C7 H7B 108.3 ?
O1 C9 H9A 109.5 ?
O1 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O1 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C7 C8 S2 113.9(3) yes
C7 C8 H8A 108.8 ?
S2 C8 H8A 108.8 ?
C7 C8 H8B 108.8 ?
S2 C8 H8B 108.8 ?
H8A C8 H8B 107.7 ?
C11 C10 C1 114.6(3) yes
C11 C10 H10A 108.6 ?
C1 C10 H10A 108.6 ?
C11 C10 H10B 108.6 ?
C1 C10 H10B 108.6 ?
H10A C10 H10B 107.6 ?
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
S1 C7 . 1.811(4) yes
S1 C2 . 1.826(3) yes
S2 C8 . 1.782(5) yes
S2 C2 . 1.852(3) yes
O1 C1 . 1.412(3) yes
O1 C9 . 1.421(4) yes
C2 C1 . 1.554(4) yes
C2 C6 . 1.560(4) yes
C1 C10 . 1.507(4) yes
C1 C3 . 1.526(4) yes
C4 C3 . 1.521(5) yes
C4 C5 . 1.532(5) yes
C4 H41 . 1.09(7) ?
C11 C10 . 1.319(4) yes
C11 C5 . 1.488(5) yes
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C3 H31 . 0.97(4) ?
C5 C6 . 1.547(6) yes
C5 H51 . 1.09(6) ?
C6 H61 . 0.87(4) ?
C6 H62 . 1.09(5) ?
C7 C8 . 1.462(6) yes
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
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
C7 S1 C2 C1 -91.5(2) ?
C7 S1 C2 C6 148.5(2) ?
C7 S1 C2 S2 30.1(2) yes
C8 S2 C2 C1 108.3(2) ?
C8 S2 C2 C6 -132.0(2) ?
C8 S2 C2 S1 -15.3(2) yes
C9 O1 C1 C10 55.4(4) ?
C9 O1 C1 C3 -71.4(3) yes
C9 O1 C1 C2 171.5(3) ?
C6 C2 C1 O1 176.4(2) ?
S1 C2 C1 O1 56.4(2) yes
S2 C2 C1 O1 -62.4(2) yes
C6 C2 C1 C10 -60.7(3) ?
S1 C2 C1 C10 179.34(17) ?
S2 C2 C1 C10 60.5(2) ?
C6 C2 C1 C3 55.8(3) ?
S1 C2 C1 C3 -64.2(2) ?
S2 C2 C1 C3 177.04(19) ?
C5 C4 C3 C1 2.8(4) ?
O1 C1 C3 C4 179.9(3) ?
C10 C1 C3 C4 50.1(3) ?
C2 C1 C3 C4 -63.1(3) ?
C10 C11 C5 C4 57.2(5) ?
C10 C11 C5 C6 -57.1(4) ?
C3 C4 C5 C11 -55.5(4) ?
C3 C4 C5 C6 60.8(3) ?
C11 C5 C6 C2 50.3(4) ?
C4 C5 C6 C2 -66.8(3) ?
C1 C2 C6 C5 7.1(3) ?
S1 C2 C6 C5 130.6(3) ?
S2 C2 C6 C5 -114.1(3) ?
C2 S1 C7 C8 -38.6(4) yes
S1 C7 C8 S2 32.1(4) yes
C2 S2 C8 C7 -10.1(4) yes
C5 C11 C10 C1 -0.6(5) ?
O1 C1 C10 C11 178.2(3) ?
C3 C1 C10 C11 -53.7(4) ?
C2 C1 C10 C11 61.0(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4410973
