#------------------------------------------------------------------------------
#$Date: 2018-09-12 13:13:09 +0300 (Wed, 12 Sep 2018) $
#$Revision: 210877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101612.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_4101612
loop_
_publ_author_name
'Fujisaki, Junichi'
'Matsumoto, Kenji'
'Matsumoto, Kazuhiro'
'Katsuki, Tsutomu'
_publ_section_title
;
 Catalytic asymmetric oxidation of cyclic dithioacetals: highly diastereo-
 and enantioselective synthesis of the S-oxides by a chiral
 aluminum(salalen) complex
;
_journal_coden_ASTM              JACSAT
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              56
_journal_page_last               61
_journal_paper_doi               10.1021/ja106877x
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C12 H12 O1 S2)'
_chemical_formula_sum            'C12 H12 O S2'
_chemical_formula_weight         236.33
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.0880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2896(14)
_cell_length_b                   5.7582(6)
_cell_length_c                   15.3496(16)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.38
_cell_volume                     1128.6(2)
_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      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12914
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_correction_T_min  0.8099
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0184
_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)+(0.0323P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0501
_reflns_number_gt                5055
_reflns_number_total             5109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106877x_si_002.cif
_cod_data_source_block           phenylethynyl_SSO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4101612
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1B S 0.152393(19) 0.67047(4) 0.051051(17) 0.01581(6) Uani 1 1 d . . .
S2B S 0.23604(2) 0.30395(5) 0.192333(17) 0.01930(7) Uani 1 1 d . . .
S1A S 0.14639(2) 0.56952(5) 0.558474(18) 0.01728(6) Uani 1 1 d . . .
S2A S 0.23140(2) 0.18646(6) 0.689999(17) 0.02171(7) Uani 1 1 d . . .
O1A O 0.08120(6) 0.60770(16) 0.46255(5) 0.02315(18) Uani 1 1 d . . .
O1B O 0.08283(6) 0.69651(16) -0.04406(5) 0.02132(17) Uani 1 1 d . . .
C2A C 0.51803(9) 0.1431(2) 0.37821(7) 0.0211(2) Uani 1 1 d . . .
C5A C 0.35799(9) -0.1617(2) 0.38512(7) 0.0186(2) Uani 1 1 d . . .
C3A C 0.44484(9) 0.2081(2) 0.42301(7) 0.0180(2) Uani 1 1 d . . .
C1A C 0.51020(9) -0.0708(2) 0.33564(7) 0.0227(2) Uani 1 1 d . . .
C4A C 0.36424(8) 0.0560(2) 0.42658(7) 0.01592(19) Uani 1 1 d . . .
C6A C 0.43002(10) -0.2225(2) 0.33885(7) 0.0225(2) Uani 1 1 d . . .
C8A C 0.23036(8) 0.1767(2) 0.51644(7) 0.0184(2) Uani 1 1 d . . .
C9A C 0.16495(8) 0.25263(19) 0.57236(7) 0.0159(2) Uani 1 1 d . . .
C7A C 0.29044(8) 0.1209(2) 0.47495(7) 0.0181(2) Uani 1 1 d . . .
C10A C 0.05508(9) 0.5960(2) 0.62704(8) 0.0199(2) Uani 1 1 d . . .
C11A C 0.12981(9) 0.2769(3) 0.74028(8) 0.0249(3) Uani 1 1 d . . .
C12A C 0.10403(10) 0.5349(2) 0.72632(8) 0.0242(2) Uani 1 1 d . . .
C2B C 0.50835(9) 0.0904(2) -0.12057(7) 0.0211(2) Uani 1 1 d . . .
C3B C 0.44321(9) 0.1906(2) -0.07465(7) 0.0187(2) Uani 1 1 d . . .
C1B C 0.48401(9) -0.1261(2) -0.16149(7) 0.0216(2) Uani 1 1 d . . .
C6B C 0.39402(9) -0.2418(2) -0.15653(7) 0.0206(2) Uani 1 1 d . . .
C5B C 0.32864(9) -0.1441(2) -0.10994(7) 0.0183(2) Uani 1 1 d . . .
C4B C 0.35262(8) 0.0741(2) -0.06893(7) 0.0170(2) Uani 1 1 d . . .
C9B C 0.16570(8) 0.35542(19) 0.07395(7) 0.0164(2) Uani 1 1 d . . .
C7B C 0.28508(8) 0.1749(2) -0.02085(7) 0.0187(2) Uani 1 1 d . . .
C8B C 0.22718(8) 0.2557(2) 0.01873(7) 0.0187(2) Uani 1 1 d . . .
C10B C 0.06905(9) 0.7275(2) 0.12403(8) 0.0201(2) Uani 1 1 d . . .
C12B C 0.12729(9) 0.6909(2) 0.22374(7) 0.0203(2) Uani 1 1 d . . .
C11B C 0.14569(9) 0.4351(2) 0.24712(8) 0.0222(2) Uani 1 1 d . . .
H2A H 0.5733(13) 0.253(3) 0.3819(11) 0.036(4) Uiso 1 1 d . . .
H3A H 0.4462(10) 0.360(3) 0.4512(9) 0.020(3) Uiso 1 1 d . . .
H1A H 0.5580(11) -0.117(3) 0.3046(9) 0.022(3) Uiso 1 1 d . . .
H5A H 0.4251(10) -0.367(3) 0.3087(9) 0.017(3) Uiso 1 1 d . . .
H4A H 0.3047(12) -0.262(3) 0.3876(11) 0.038(4) Uiso 1 1 d . . .
H6A H 0.0972(11) 0.189(3) 0.5544(9) 0.024(4) Uiso 1 1 d . . .
H8A H -0.0033(10) 0.499(3) 0.6014(8) 0.014(3) Uiso 1 1 d . . .
H10A H 0.0682(11) 0.188(3) 0.7153(9) 0.023(4) Uiso 1 1 d . . .
H7A H 0.0367(12) 0.760(3) 0.6197(10) 0.029(4) Uiso 1 1 d . . .
H9A H 0.1577(12) 0.246(3) 0.8037(11) 0.037(4) Uiso 1 1 d . . .
H11A H 0.0557(12) 0.576(3) 0.7591(10) 0.032(4) Uiso 1 1 d . . .
H12A H 0.1697(13) 0.631(3) 0.7489(11) 0.037(4) Uiso 1 1 d . . .
H6B H 0.0928(11) 0.293(3) 0.0587(9) 0.025(4) Uiso 1 1 d . . .
H8B H 0.0067(11) 0.628(3) 0.1075(9) 0.019(3) Uiso 1 1 d . . .
H4B H 0.2683(11) -0.215(3) -0.1067(9) 0.026(4) Uiso 1 1 d . . .
H10B H 0.0770(13) 0.344(3) 0.2289(11) 0.038(4) Uiso 1 1 d . . .
H12B H 0.1937(10) 0.771(2) 0.2391(8) 0.012(3) Uiso 1 1 d . . .
H2B H 0.5708(12) 0.172(3) -0.1193(10) 0.032(4) Uiso 1 1 d . . .
H5B H 0.3762(10) -0.385(3) -0.1834(9) 0.017(3) Uiso 1 1 d . . .
H1B H 0.5318(10) -0.192(3) -0.1928(9) 0.020(3) Uiso 1 1 d . . .
H11B H 0.0874(11) 0.760(3) 0.2592(9) 0.022(3) Uiso 1 1 d . . .
H7B H 0.0516(11) 0.894(3) 0.1110(10) 0.026(4) Uiso 1 1 d . . .
H3B H 0.4572(10) 0.338(3) -0.0474(9) 0.018(3) Uiso 1 1 d . . .
H9B H 0.1802(11) 0.407(3) 0.3122(9) 0.025(4) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1B S1B C10B 105.41(5) . . ?
O1B S1B C9B 106.46(5) . . ?
C10B S1B C9B 95.93(5) . . ?
C11B S2B C9B 99.92(5) . . ?
O1A S1A C10A 104.99(5) . . ?
O1A S1A C9A 106.26(5) . . ?
C10A S1A C9A 96.04(5) . . ?
C11A S2A C9A 98.57(5) . . ?
C1A C2A C3A 120.14(11) . . ?
C1A C2A H2A 124.8(10) . . ?
C3A C2A H2A 115.0(10) . . ?
C6A C5A C4A 119.83(10) . . ?
C6A C5A H4A 120.6(11) . . ?
C4A C5A H4A 119.5(11) . . ?
C2A C3A C4A 120.02(11) . . ?
C2A C3A H3A 122.2(8) . . ?
C4A C3A H3A 117.8(8) . . ?
C2A C1A C6A 120.04(10) . . ?
C2A C1A H1A 121.6(10) . . ?
C6A C1A H1A 118.3(10) . . ?
C3A C4A C5A 119.61(10) . . ?
C3A C4A C7A 119.93(10) . . ?
C5A C4A C7A 120.43(10) . . ?
C5A C6A C1A 120.34(11) . . ?
C5A C6A H5A 120.6(8) . . ?
C1A C6A H5A 119.0(8) . . ?
C7A C8A C9A 175.19(11) . . ?
C8A C9A S2A 108.63(8) . . ?
C8A C9A S1A 108.24(8) . . ?
S2A C9A S1A 109.55(6) . . ?
C8A C9A H6A 113.1(9) . . ?
S2A C9A H6A 111.9(9) . . ?
S1A C9A H6A 105.3(10) . . ?
C8A C7A C4A 178.84(12) . . ?
C12A C10A S1A 113.01(8) . . ?
C12A C10A H8A 110.6(8) . . ?
S1A C10A H8A 108.1(8) . . ?
C12A C10A H7A 111.4(9) . . ?
S1A C10A H7A 101.5(9) . . ?
H8A C10A H7A 111.9(13) . . ?
C12A C11A S2A 112.68(9) . . ?
C12A C11A H10A 109.3(10) . . ?
S2A C11A H10A 109.5(9) . . ?
C12A C11A H9A 109.4(11) . . ?
S2A C11A H9A 104.8(9) . . ?
H10A C11A H9A 111.0(13) . . ?
C10A C12A C11A 112.48(10) . . ?
C10A C12A H11A 108.0(9) . . ?
C11A C12A H11A 109.0(11) . . ?
C10A C12A H12A 107.8(10) . . ?
C11A C12A H12A 110.3(10) . . ?
H11A C12A H12A 109.2(14) . . ?
C3B C2B C1B 120.18(11) . . ?
C3B C2B H2B 116.8(10) . . ?
C1B C2B H2B 122.9(10) . . ?
C2B C3B C4B 120.07(11) . . ?
C2B C3B H3B 121.8(8) . . ?
C4B C3B H3B 118.1(8) . . ?
C6B C1B C2B 120.02(11) . . ?
C6B C1B H1B 121.8(9) . . ?
C2B C1B H1B 118.2(9) . . ?
C5B C6B C1B 120.34(11) . . ?
C5B C6B H5B 118.2(8) . . ?
C1B C6B H5B 121.5(8) . . ?
C6B C5B C4B 119.83(10) . . ?
C6B C5B H4B 122.0(10) . . ?
C4B C5B H4B 118.1(10) . . ?
C5B C4B C3B 119.54(10) . . ?
C5B C4B C7B 119.82(10) . . ?
C3B C4B C7B 120.63(11) . . ?
C8B C9B S2B 107.59(7) . . ?
C8B C9B S1B 108.53(8) . . ?
S2B C9B S1B 110.18(6) . . ?
C8B C9B H6B 112.8(9) . . ?
S2B C9B H6B 111.8(8) . . ?
S1B C9B H6B 105.9(10) . . ?
C8B C7B C4B 178.68(12) . . ?
C7B C8B C9B 174.59(11) . . ?
C12B C10B S1B 111.60(8) . . ?
C12B C10B H8B 109.6(8) . . ?
S1B C10B H8B 110.5(8) . . ?
C12B C10B H7B 111.2(8) . . ?
S1B C10B H7B 101.5(9) . . ?
H8B C10B H7B 112.3(12) . . ?
C11B C12B C10B 112.00(10) . . ?
C11B C12B H12B 109.3(8) . . ?
C10B C12B H12B 110.7(7) . . ?
C11B C12B H11B 110.6(9) . . ?
C10B C12B H11B 108.0(8) . . ?
H12B C12B H11B 106.1(11) . . ?
C12B C11B S2B 112.25(8) . . ?
C12B C11B H10B 111.1(10) . . ?
S2B C11B H10B 108.4(10) . . ?
C12B C11B H9B 113.2(10) . . ?
S2B C11B H9B 102.7(8) . . ?
H10B C11B H9B 108.7(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1B O1B 1.5035(8) . ?
S1B C10B 1.8104(11) . ?
S1B C9B 1.8470(11) . ?
S2B C11B 1.8108(12) . ?
S2B C9B 1.8227(11) . ?
S1A O1A 1.5032(8) . ?
S1A C10A 1.8197(12) . ?
S1A C9A 1.8458(12) . ?
S2A C11A 1.8075(12) . ?
S2A C9A 1.8171(11) . ?
C2A C1A 1.3845(18) . ?
C2A C3A 1.3892(15) . ?
C2A H2A 0.959(17) . ?
C5A C6A 1.3855(16) . ?
C5A C4A 1.3981(15) . ?
C5A H4A 0.924(17) . ?
C3A C4A 1.3964(15) . ?
C3A H3A 0.975(15) . ?
C1A C6A 1.3892(18) . ?
C1A H1A 0.933(14) . ?
C4A C7A 1.4340(14) . ?
C6A H5A 0.945(15) . ?
C8A C7A 1.1950(16) . ?
C8A C9A 1.4482(14) . ?
C9A H6A 0.940(15) . ?
C10A C12A 1.5231(16) . ?
C10A H8A 0.950(14) . ?
C10A H7A 0.971(18) . ?
C11A C12A 1.5264(19) . ?
C11A H10A 0.950(15) . ?
C11A H9A 0.958(16) . ?
C12A H11A 0.949(15) . ?
C12A H12A 1.011(17) . ?
C2B C3B 1.3848(16) . ?
C2B C1B 1.3926(18) . ?
C2B H2B 0.949(16) . ?
C3B C4B 1.4021(16) . ?
C3B H3B 0.940(15) . ?
C1B C6B 1.3893(17) . ?
C1B H1B 0.974(13) . ?
C6B C5B 1.3882(16) . ?
C6B H5B 0.923(15) . ?
C5B C4B 1.4019(16) . ?
C5B H4B 0.914(15) . ?
C4B C7B 1.4334(15) . ?
C9B C8B 1.4490(15) . ?
C9B H6B 0.999(15) . ?
C7B C8B 1.1985(16) . ?
C10B C12B 1.5262(15) . ?
C10B H8B 0.982(15) . ?
C10B H7B 0.991(17) . ?
C12B C11B 1.5196(18) . ?
C12B H12B 0.965(13) . ?
C12B H11B 0.946(14) . ?
C11B H10B 1.023(17) . ?
C11B H9B 0.990(14) . ?
