#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225227.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_2225227
loop_
_publ_author_name
'Wardell, Solange M. S. V.'
'Wardell, James L.'
'de Lima, Geraldo M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 meso-1-{[2-(Propyl-1-sulfinyl)ethyl]sulfinyl}propane
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o647
_journal_page_last               o648
_journal_paper_doi               10.1107/S1600536810005799
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H18 O2 S2'
_chemical_formula_moiety         'C8 H18 O2 S2'
_chemical_formula_sum            'C8 H18 O2 S2'
_chemical_formula_weight         210.34
_chemical_name_common
;
meso-1-{[2-(Propane-1-sulfinyl)ethane]sulfinyl}propane
;
_chemical_name_systematic
;
meso-1-{[2-(Propyl-1-sulfinyl)ethyl]sulfinyl}propane
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 97.191(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9794(9)
_cell_length_b                   5.2190(3)
_cell_length_c                   8.7618(5)
_cell_measurement_reflns_used    19160
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     543.48(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5666
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.4
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.4193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.078
_refine_ls_wR_factor_ref         0.080
_reflns_number_gt                1167
_reflns_number_total             1239
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2201.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225227
_cod_database_fobs_code          2225227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
S S1 0.66819(3) -0.09909(6) 0.45405(4) 0.01305(14) Uani d . 1 . .
O O1 0.64458(10) -0.37397(19) 0.40786(13) 0.0187(3) Uani d . 1 . .
C C1 0.72083(12) 0.0560(3) 0.29375(16) 0.0149(3) Uani d . 1 . .
H H1A 0.6705 0.0192 0.1978 0.018 Uiso calc R 1 . .
H H1B 0.7228 0.2438 0.3097 0.018 Uiso calc R 1 . .
C C2 0.83896(12) -0.0425(3) 0.27975(17) 0.0191(3) Uani d . 1 . .
H H2A 0.8363 -0.2305 0.2646 0.023 Uiso calc R 1 . .
H H2B 0.8885 -0.0065 0.3765 0.023 Uiso calc R 1 . .
C C3 0.88818(14) 0.0828(3) 0.14553(19) 0.0246(4) Uani d . 1 . .
H H3A 0.8398 0.0455 0.0494 0.037 Uiso calc R 1 . .
H H3B 0.9638 0.0147 0.1397 0.037 Uiso calc R 1 . .
H H3C 0.8925 0.2686 0.1614 0.037 Uiso calc R 1 . .
C C4 0.53341(12) 0.0583(3) 0.44006(15) 0.0144(3) Uani d . 1 . .
H H4A 0.5438 0.2443 0.4589 0.017 Uiso calc R 1 . .
H H4B 0.4924 0.0343 0.3358 0.017 Uiso calc R 1 . .
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 0.0150(2) 0.0110(2) 0.0135(2) 0.00060(11) 0.00307(13) 0.00048(11)
O1 0.0238(6) 0.0087(5) 0.0244(6) 0.0012(4) 0.0066(4) 0.0004(4)
C1 0.0176(7) 0.0133(6) 0.0147(6) -0.0002(5) 0.0048(5) 0.0007(5)
C2 0.0179(7) 0.0221(7) 0.0181(7) 0.0014(6) 0.0057(5) 0.0005(6)
C3 0.0210(8) 0.0325(9) 0.0217(7) -0.0031(6) 0.0078(6) 0.0010(6)
C4 0.0167(7) 0.0111(6) 0.0162(6) 0.0018(5) 0.0049(5) 0.0013(5)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 C4 . . 106.20(7) ?
O1 S1 C1 . . 106.88(7) ?
C4 S1 C1 . . 98.06(6) ?
C2 C1 S1 . . 109.27(10) ?
C2 C1 H1A . . 109.8 ?
S1 C1 H1A . . 109.8 ?
C2 C1 H1B . . 109.8 ?
S1 C1 H1B . . 109.8 ?
H1A C1 H1B . . 108.3 ?
C1 C2 C3 . . 111.67(13) ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 107.9 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
C4 C4 S1 3_656 . 108.34(13) ?
C4 C4 H4A 3_656 . 110.0 ?
S1 C4 H4A . . 110.0 ?
C4 C4 H4B 3_656 . 110.0 ?
S1 C4 H4B . . 110.0 ?
H4A C4 H4B . . 108.4 ?
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 O1 . 1.5077(10) ?
S1 C4 . 1.8018(14) ?
S1 C1 . 1.8021(14) ?
C1 C2 . 1.525(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.527(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 C4 3_656 1.525(3) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1b O1 1_565 0.99 2.41 3.3035(19) 150
C4 H4a O1 1_565 0.99 2.40 3.2751(19) 147
C4 H4b O1 2_655 0.99 2.57 3.5124(18) 159
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . -71.04(11) ?
C4 S1 C1 C2 . . . . 179.23(10) ?
S1 C1 C2 C3 . . . . -179.93(11) ?
O1 S1 C4 C4 . . . 3_656 65.40(14) ?
C1 S1 C4 C4 . . . 3_656 175.68(13) ?
