#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/67/1506702.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_1506702
loop_
_publ_author_name
'Wedel, Tobias'
'Podlech, Joachim'
_publ_section_title
;
 Enolate addition to a 2-alkylidene[1,3]dithiane-derived bissulfoxide. A
 new a(2)-acceptor.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4013
_journal_page_last               4015
_journal_paper_doi               10.1021/ol051670i
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C11 H12 O2 S2'
_chemical_formula_weight         240.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.613(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4794(3)
_cell_length_b                   6.8463(3)
_cell_length_c                   10.1247(5)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      26
_cell_volume                     571.25(4)
_computing_cell_refinement       'Bruker Xscans v.2.31'
_computing_data_collection       'Bruker Xscans v.2.31'
_computing_data_reduction        'Bruker Xscans v.2.31'
_computing_molecular_graphics    'SHELXTL - XP'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'Omega - Scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2186
_diffrn_reflns_theta_full        67.98
_diffrn_reflns_theta_max         67.98
_diffrn_reflns_theta_min         4.49
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.042
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                1806
_reflns_number_total             1899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol051670isi20050718_023318.cif
_cod_data_source_block           s1111rc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Psi-Scan' changed to
'psi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1506702
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
_atom_site_refinement_flags
S1 S 0.77082(11) 0.04034(13) 0.58110(10) 0.0550(3) Uani 1 1 d .
C1 C 0.8543(4) 0.2538(6) 0.6750(4) 0.0508(9) Uani 1 1 d .
O1 O 0.9032(4) -0.1065(5) 0.6032(4) 0.0751(9) Uani 1 1 d .
S2 S 0.71700(11) 0.45543(13) 0.65484(9) 0.0552(3) Uani 1 1 d .
O2 O 0.5558(3) 0.3670(5) 0.6561(3) 0.0688(8) Uani 1 1 d .
C2 C 0.7602(5) 0.1454(7) 0.4169(4) 0.0581(9) Uani 1 1 d .
H2A H 0.8690 0.1790 0.4097 0.070 Uiso 1 1 calc R
H2B H 0.7180 0.0483 0.3478 0.070 Uiso 1 1 calc R
C3 C 0.6541(5) 0.3267(6) 0.3888(4) 0.0607(10) Uani 1 1 d .
H3A H 0.6441 0.3652 0.2950 0.073 Uiso 1 1 calc R
H3B H 0.5465 0.2930 0.3989 0.073 Uiso 1 1 calc R
C4 C 0.7143(5) 0.5005(6) 0.4788(4) 0.0592(10) Uani 1 1 d .
H4A H 0.6449 0.6118 0.4471 0.071 Uiso 1 1 calc R
H4B H 0.8231 0.5333 0.4712 0.071 Uiso 1 1 calc R
C5 C 1.0037(5) 0.2394(6) 0.7568(4) 0.0542(9) Uani 1 1 d .
H5 H 1.0524 0.1185 0.7526 0.065 Uiso 1 1 calc R
C6 C 1.1052(5) 0.3765(7) 0.8513(4) 0.0596(10) Uani 1 1 d .
C7 C 1.0728(6) 0.5732(7) 0.8636(4) 0.0657(11) Uani 1 1 d .
H7 H 0.9818 0.6298 0.8071 0.079 Uiso 1 1 calc R
C8 C 1.1763(7) 0.6847(10) 0.9604(5) 0.0876(17) Uani 1 1 d .
H8 H 1.1550 0.8167 0.9693 0.105 Uiso 1 1 calc R
C9 C 1.3128(8) 0.5991(16) 1.0447(6) 0.117(3) Uani 1 1 d .
H9 H 1.3816 0.6737 1.1107 0.140 Uiso 1 1 calc R
C10 C 1.3450(9) 0.4101(17) 1.0307(8) 0.129(3) Uani 1 1 d .
H10 H 1.4376 0.3548 1.0859 0.155 Uiso 1 1 calc R
C11 C 1.2436(7) 0.2978(13) 0.9365(6) 0.101(2) Uani 1 1 d .
H11 H 1.2672 0.1662 0.9290 0.121 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0400(5) 0.0513(5) 0.0727(6) -0.0040(4) 0.0111(4) -0.0013(4)
C1 0.037(2) 0.060(2) 0.0548(19) -0.0015(16) 0.0089(16) 0.0031(16)
O1 0.0590(19) 0.0529(14) 0.107(2) -0.0109(15) 0.0069(16) 0.0124(13)
S2 0.0419(5) 0.0571(5) 0.0649(5) -0.0037(4) 0.0091(4) 0.0093(4)
O2 0.0415(15) 0.0848(19) 0.0824(18) 0.0103(16) 0.0197(13) 0.0092(14)
C2 0.043(2) 0.068(2) 0.064(2) -0.0174(18) 0.0158(17) -0.0112(19)
C3 0.046(2) 0.068(2) 0.065(2) 0.0031(19) 0.0077(18) -0.0070(19)
C4 0.044(2) 0.058(2) 0.073(2) 0.0096(18) 0.0085(17) 0.0030(16)
C5 0.038(2) 0.0615(19) 0.062(2) 0.0038(16) 0.0087(16) 0.0045(16)
C6 0.042(2) 0.081(3) 0.054(2) -0.0030(19) 0.0087(17) -0.002(2)
C7 0.056(2) 0.077(3) 0.065(2) -0.012(2) 0.015(2) -0.009(2)
C8 0.081(4) 0.104(4) 0.085(3) -0.035(3) 0.035(3) -0.026(3)
C9 0.068(4) 0.198(10) 0.079(3) -0.057(5) 0.007(3) -0.037(5)
C10 0.085(5) 0.167(8) 0.108(5) -0.045(5) -0.035(4) 0.006(5)
C11 0.063(3) 0.122(5) 0.098(4) -0.015(4) -0.022(3) 0.014(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 C2 106.4(2)
O1 S1 C1 106.36(18)
C2 S1 C1 95.29(18)
C5 C1 S2 128.5(3)
C5 C1 S1 117.6(3)
S2 C1 S1 113.80(19)
O2 S2 C1 104.95(19)
O2 S2 C4 106.14(18)
C1 S2 C4 95.83(17)
C3 C2 S1 113.5(3)
C3 C2 H2A 108.9
S1 C2 H2A 108.9
C3 C2 H2B 108.9
S1 C2 H2B 108.9
H2A C2 H2B 107.7
C4 C3 C2 115.4(3)
C4 C3 H3A 108.4
C2 C3 H3A 108.4
C4 C3 H3B 108.4
C2 C3 H3B 108.4
H3A C3 H3B 107.5
C3 C4 S2 112.6(3)
C3 C4 H4A 109.1
S2 C4 H4A 109.1
C3 C4 H4B 109.1
S2 C4 H4B 109.1
H4A C4 H4B 107.8
C1 C5 C6 132.7(4)
C1 C5 H5 113.6
C6 C5 H5 113.6
C7 C6 C11 118.5(5)
C7 C6 C5 125.6(4)
C11 C6 C5 115.9(5)
C8 C7 C6 119.6(5)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 119.9(6)
C7 C8 H8 120.0
C9 C8 H8 120.0
C10 C9 C8 120.2(6)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 120.6(7)
C9 C10 H10 119.7
C11 C10 H10 119.7
C10 C11 C6 121.1(8)
C10 C11 H11 119.4
C6 C11 H11 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.484(3)
S1 C2 1.794(4)
S1 C1 1.796(4)
C1 C5 1.344(6)
C1 S2 1.786(4)
S2 O2 1.498(3)
S2 C4 1.804(4)
C2 C3 1.520(6)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.512(6)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.466(6)
C5 H5 0.9300
C6 C7 1.386(7)
C6 C11 1.391(7)
C7 C8 1.381(7)
C7 H7 0.9300
C8 C9 1.395(10)
C8 H8 0.9300
C9 C10 1.336(14)
C9 H9 0.9300
C10 C11 1.362(9)
C10 H10 0.9300
C11 H11 0.9300
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
O1 S1 C1 C5 -7.5(4)
C2 S1 C1 C5 -116.4(3)
O1 S1 C1 S2 176.8(2)
C2 S1 C1 S2 67.9(2)
C5 C1 S2 O2 -134.9(4)
S1 C1 S2 O2 40.2(2)
C5 C1 S2 C4 116.6(4)
S1 C1 S2 C4 -68.3(2)
O1 S1 C2 C3 -168.5(3)
C1 S1 C2 C3 -59.7(3)
S1 C2 C3 C4 65.0(4)
C2 C3 C4 S2 -64.5(4)
O2 S2 C4 C3 -47.5(3)
C1 S2 C4 C3 59.9(3)
S2 C1 C5 C6 -1.8(7)
S1 C1 C5 C6 -176.7(4)
C1 C5 C6 C7 -9.4(7)
C1 C5 C6 C11 169.3(5)
C11 C6 C7 C8 -0.8(7)
C5 C6 C7 C8 177.8(4)
C6 C7 C8 C9 0.2(7)
C7 C8 C9 C10 1.0(10)
C8 C9 C10 C11 -1.5(14)
C9 C10 C11 C6 0.8(14)
C7 C6 C11 C10 0.4(10)
C5 C6 C11 C10 -178.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21157011 ChemSpider
