#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/39/4113988.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_4113988
loop_
_publ_author_name
'Sanae Tanaka'
'Yoshiaki Sugihara'
'Akira Sakamoto'
'Akihiko Ishii'
'Juzo Nakayama'
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science, Saitama University
sakura-ku, Saitama, Saitama 338-8570, Japan
;
_publ_contact_author_email       nakaj@post.saitama-u.ac.jp
_publ_contact_author_fax         +81-48-858-3700
_publ_contact_author_name        'Dr. Juzo Nakayama'
_publ_contact_author_phone       +81-48-858-3390
_publ_section_title
;
 The Thiosulfinyl Group Serves as a Stereogenic Center and Shows
 Diamagnetic Anisotropy Similar to That of the Sulfinyl Group
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9024
_journal_page_last               9025
_journal_paper_doi               10.1021/ja035892s
_journal_volume                  125
_journal_year                    2003
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C12 H22 O2 S3 '
_chemical_formula_sum            'C12 H22 O2 S3'
_chemical_formula_weight         294.498
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 109.3810(20)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6600(3)
_cell_length_b                   13.2410(6)
_cell_length_c                   13.1402(8)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    153
_cell_volume                     1421.36(12)
_computing_cell_refinement       'HKL Scalepack'
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'DIP Image plate'
_diffrn_measurement_method       IP
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3241
_diffrn_reflns_theta_full        27.07
_diffrn_reflns_theta_max         27.07
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       Cube
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2500
_reflns_number_total             3103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja035892ssi20030501_042556.cif
_cod_data_source_block           global
_cod_original_cell_volume        1424.16(12)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C12 H22 O2 S3 '
_cod_database_code               4113988
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
'-X,+Y+ 1/2,-Z+ 1/2'
'+X,-Y+ 1/2,+Z+ 1/2'
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
S1 S 0.05898(5) 0.14013(3) 0.53582(3) 0.02267(12) Uani 1 1 d
S2 S 0.23836(6) 0.32185(3) 0.81974(4) 0.03294(14) Uani 1 1 d
S3 S -0.12331(6) 0.23015(4) 0.48535(4) 0.03138(14) Uani 1 1 d
O4 O 0.06103(13) 0.08102(9) 0.64592(9) 0.0203(3) Uani 1 1 d
O5 O 0.21755(13) 0.21053(9) 0.59908(9) 0.0221(3) Uani 1 1 d
C6 C 0.17142(18) 0.12772(12) 0.74364(13) 0.0176(3) Uani 1 1 d
C7 C 0.1903(2) 0.04739(12) 0.83413(14) 0.0213(4) Uani 1 1 d
C8 C 0.0875(2) 0.22516(13) 0.76632(15) 0.0217(4) Uani 1 1 d
C9 C 0.31673(19) 0.16957(12) 0.70552(13) 0.0189(3) Uani 1 1 d
C10 C 0.45533(19) 0.10417(13) 0.68513(14) 0.0220(4) Uani 1 1 d
C11 C 0.2411(3) -0.05771(14) 0.80715(18) 0.0290(4) Uani 1 1 d
C12 C 0.3881(2) 0.01542(15) 0.60838(16) 0.0266(4) Uani 1 1 d
C13 C 0.5813(2) 0.06642(17) 0.78985(17) 0.0299(4) Uani 1 1 d
C14 C 0.3892(2) 0.26325(14) 0.77169(17) 0.0273(4) Uani 1 1 d
C15 C 0.0215(2) 0.03053(17) 0.84787(19) 0.0306(4) Uani 1 1 d
C16 C 0.5501(2) 0.17107(17) 0.6299(2) 0.0341(5) Uani 1 1 d
C17 C 0.3071(3) 0.08545(16) 0.94139(15) 0.0295(4) Uani 1 1 d
H8A H 0.011(3) 0.2483(16) 0.7041(19) 0.039(6) Uiso 1 1 d
H8B H 0.029(2) 0.2166(14) 0.8139(16) 0.023(5) Uiso 1 1 d
H11A H 0.242(2) -0.1016(15) 0.8654(17) 0.029(5) Uiso 1 1 d
H11B H 0.343(2) -0.0588(13) 0.7957(15) 0.021(5) Uiso 1 1 d
H11C H 0.167(3) -0.0851(17) 0.7458(19) 0.042(6) Uiso 1 1 d
H12A H 0.481(3) -0.0245(17) 0.6034(17) 0.042(6) Uiso 1 1 d
H12B H 0.329(3) 0.0378(15) 0.5387(18) 0.034(6) Uiso 1 1 d
H12C H 0.323(3) -0.0269(17) 0.6316(19) 0.045(6) Uiso 1 1 d
H13A H 0.658(3) 0.0239(17) 0.7707(18) 0.042(6) Uiso 1 1 d
H13B H 0.532(3) 0.0257(19) 0.836(2) 0.058(7) Uiso 1 1 d
H13C H 0.638(3) 0.1161(18) 0.8241(19) 0.043(7) Uiso 1 1 d
H14A H 0.421(2) 0.3083(16) 0.7271(18) 0.038(6) Uiso 1 1 d
H14B H 0.486(3) 0.2448(15) 0.8384(18) 0.034(5) Uiso 1 1 d
H15A H 0.032(2) -0.0292(17) 0.8945(17) 0.037(6) Uiso 1 1 d
H15B H -0.055(3) 0.0196(17) 0.7801(19) 0.041(6) Uiso 1 1 d
H15C H -0.008(2) 0.0854(16) 0.8820(17) 0.032(5) Uiso 1 1 d
H16A H 0.627(3) 0.1325(16) 0.6129(18) 0.034(6) Uiso 1 1 d
H16B H 0.607(3) 0.2278(18) 0.6749(19) 0.043(6) Uiso 1 1 d
H16C H 0.481(3) 0.2000(16) 0.5597(19) 0.037(6) Uiso 1 1 d
H17A H 0.309(3) 0.0367(17) 0.9966(19) 0.045(6) Uiso 1 1 d
H17B H 0.265(3) 0.1480(17) 0.9650(17) 0.036(6) Uiso 1 1 d
H17C H 0.419(3) 0.0902(17) 0.9440(17) 0.039(6) 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
O4 S1 O5 93.32(6)
O4 S1 S3 111.88(5)
O5 S1 S3 106.28(5)
C8 S2 C14 94.25(8)
C6 O4 S1 112.83(9)
C9 O5 S1 113.60(9)
O4 C6 C8 107.82(12)
O4 C6 C7 104.82(12)
C8 C6 C7 110.96(13)
O4 C6 C9 103.13(12)
C8 C6 C9 103.73(13)
C7 C6 C9 125.22(13)
C17 C7 C11 111.03(15)
C17 C7 C15 107.83(16)
C11 C7 C15 104.43(15)
C17 C7 C6 110.53(14)
C11 C7 C6 114.06(14)
C15 C7 C6 108.59(14)
C6 C8 S2 109.84(11)
O5 C9 C14 104.09(13)
O5 C9 C10 106.25(13)
C14 C9 C10 110.47(13)
O5 C9 C6 98.59(11)
C14 C9 C6 108.82(14)
C10 C9 C6 125.84(13)
C13 C10 C12 110.25(15)
C13 C10 C16 106.13(15)
C12 C10 C16 106.08(16)
C13 C10 C9 112.66(15)
C12 C10 C9 112.76(13)
C16 C10 C9 108.50(14)
C9 C14 S2 109.82(12)
C6 C8 H8A 110.5(14)
S2 C8 H8A 109.1(14)
C6 C8 H8B 114.8(12)
S2 C8 H8B 108.1(12)
H8A C8 H8B 104.2(18)
C7 C11 H11A 107.2(12)
C7 C11 H11B 113.8(11)
H11A C11 H11B 110.5(16)
C7 C11 H11C 112.8(14)
H11A C11 H11C 106.4(18)
H11B C11 H11C 106.0(17)
C10 C12 H12A 108.2(13)
C10 C12 H12B 111.6(13)
H12A C12 H12B 107.6(18)
C10 C12 H12C 113.2(14)
H12A C12 H12C 107.5(18)
H12B C12 H12C 108.6(18)
C10 C13 H13A 107.7(13)
C10 C13 H13B 113.8(14)
H13A C13 H13B 107.9(19)
C10 C13 H13C 109.9(16)
H13A C13 H13C 105.0(19)
H13B C13 H13C 112(2)
C9 C14 H14A 108.1(13)
S2 C14 H14A 110.0(13)
C9 C14 H14B 111.3(12)
S2 C14 H14B 106.6(12)
H14A C14 H14B 111.0(17)
C7 C15 H15A 106.6(12)
C7 C15 H15B 108.5(13)
H15A C15 H15B 111.3(18)
C7 C15 H15C 111.4(13)
H15A C15 H15C 108.1(17)
H15B C15 H15C 110.8(18)
C10 C16 H16A 109.4(13)
C10 C16 H16B 113.2(14)
H16A C16 H16B 108.3(18)
C10 C16 H16C 113.7(12)
H16A C16 H16C 104.7(19)
H16B C16 H16C 107.1(18)
C7 C17 H17A 108.4(14)
C7 C17 H17B 111.4(12)
H17A C17 H17B 103.9(18)
C7 C17 H17C 114.2(13)
H17A C17 H17C 104.4(19)
H17B C17 H17C 113.6(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.6399(12)
S1 O5 1.6432(12)
S1 S3 1.9154(6)
S2 C8 1.8000(18)
S2 C14 1.8017(19)
O4 C6 1.4640(18)
O5 C9 1.4844(19)
C6 C8 1.557(2)
C6 C7 1.564(2)
C6 C9 1.598(2)
C7 C17 1.527(3)
C7 C11 1.535(2)
C7 C15 1.546(2)
C9 C14 1.527(2)
C9 C10 1.572(2)
C10 C13 1.534(3)
C10 C12 1.534(3)
C10 C16 1.541(2)
C8 H8A 0.92(2)
C8 H8B 0.93(2)
C11 H11A 0.96(2)
C11 H11B 0.943(19)
C11 H11C 0.93(2)
C12 H12A 0.98(2)
C12 H12B 0.94(2)
C12 H12C 0.92(2)
C13 H13A 0.96(2)
C13 H13B 1.01(3)
C13 H13C 0.86(2)
C14 H14A 0.94(2)
C14 H14B 1.02(2)
C15 H15A 0.99(2)
C15 H15B 0.93(2)
C15 H15C 0.93(2)
C16 H16A 0.92(2)
C16 H16B 0.98(2)
C16 H16C 1.00(2)
C17 H17A 0.97(2)
C17 H17B 0.99(2)
C17 H17C 0.96(2)
