#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200220.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_2200220
loop_
_publ_author_name
'Kansikas, Jarno'
'Sipilä, Kaija'
_publ_section_title
;(1S*,2R*,2'R*)-2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol
 at 193K
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o335
_journal_page_last               o337
_journal_paper_doi               10.1107/S160053680100438X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C20 H24 O2 S2'
_chemical_formula_moiety         'C20 H24 O2 S2'
_chemical_formula_sum            'C20 H24 O2 S2'
_chemical_formula_weight         360.51
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2440(18)
_cell_length_b                   19.239(4)
_cell_length_c                   10.682(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      4
_cell_volume                     1896.5(6)
_computing_cell_refinement       'AFC-7S software'
_computing_data_collection       'AFC-7S software'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full .964
_diffrn_measured_fraction_theta_max .964
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0289
_diffrn_reflns_av_sigmaI/netI    .0541
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3637
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .290
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             768
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_refine_diff_density_max         .277
_refine_diff_density_min         -.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          .0780
_refine_ls_R_factor_gt           .0460
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0501P)²+0.1099P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1069
_reflns_number_gt                2438
_reflns_number_total             3418
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6010.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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      'P 21/c'
_cod_database_code               2200220
_cod_database_fobs_code          2200220
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_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
S1 .61079(7) .30678(4) .07364(6) .0355(2) Uani d . 1 . . S
O1 .39674(19) .21467(9) -.04576(15) .0329(4) Uani d . 1 . . O
H1A .3562 .1792 -.0773 .049 Uiso calc R 1 . . H
C1 .4319(3) .28763(12) .1302(2) .0252(5) Uani d . 1 . . C
H1B .4395 .2883 .2239 .030 Uiso calc R 1 . . H
S2 .31071(7) .35720(3) .07562(6) .02717(17) Uani d . 1 . . S
O2 .2771(2) .39432(9) .31726(15) .0333(4) Uani d . 1 . . O
C2 .3857(3) .21387(13) .0866(2) .0272(6) Uani d . 1 . . C
C3 .4888(3) .15934(14) .1449(3) .0379(7) Uani d . 1 . . C
H3A .4579 .1130 .1160 .057 Uiso calc R 1 . . H
H3B .4875 .1616 .2365 .057 Uiso calc R 1 . . H
H3C .5873 .1684 .1197 .057 Uiso calc R 1 . . H
C4 .6601(3) .37767(14) .1741(2) .0320(6) Uani d . 1 . . C
C5 .6929(3) .36759(14) .3006(3) .0360(6) Uani d . 1 . . C
H5A .6862 .3224 .3358 .043 Uiso calc R 1 . . H
C6 .7355(3) .42303(15) .3758(3) .0425(7) Uani d . 1 . . C
H6A .7576 .4160 .4629 .051 Uiso calc R 1 . . H
C7 .7461(3) .48869(15) .3253(3) .0427(7) Uani d . 1 . . C
H7A .7761 .5268 .3772 .051 Uiso calc R 1 . . H
C8 .7132(3) .49868(15) .1999(3) .0432(7) Uani d . 1 . . C
H8A .7210 .5438 .1650 .052 Uiso calc R 1 . . H
C9 .6686(3) .44362(14) .1235(3) .0368(7) Uani d . 1 . . C
H9A .6440 .4511 .0370 .044 Uiso calc R 1 . . H
C10 .2298(3) .20079(12) .1215(2) .0249(5) Uani d . 1 . . C
C11 .1150(3) .21167(14) .0344(2) .0326(6) Uani d . 1 . . C
H11A .1334 .2230 -.0497 .039 Uiso calc R 1 . . H
C12 -.0263(3) .20616(15) .0692(3) .0419(7) Uani d . 1 . . C
H12A -.1040 .2148 .0091 .050 Uiso calc R 1 . . H
C13 -.0558(3) .18841(15) .1891(3) .0429(7) Uani d . 1 . . C
H13A -.1532 .1852 .2123 .051 Uiso calc R 1 . . H
C14 .0581(3) .17519(14) .2764(3) .0365(7) Uani d . 1 . . C
H14A .0390 .1612 .3591 .044 Uiso calc R 1 . . H
C15 .1994(3) .18243(13) .2426(2) .0296(6) Uani d . 1 . . C
H15A .2770 .1747 .3034 .036 Uiso calc R 1 . . H
C16 .1978(3) .36796(13) .2092(2) .0280(6) Uani d . 1 . . C
H16A .1601 .3210 .2310 .034 Uiso calc R 1 . . H
C17 .0689(3) .41334(14) .1720(3) .0354(6) Uani d . 1 . . C
H17A -.0033 .4099 .2366 .043 Uiso calc R 1 . . H
H17B .0228 .3965 .0917 .043 Uiso calc R 1 . . H
C18 .1132(3) .48914(14) .1576(3) .0381(7) Uani d . 1 . . C
H18A .1735 .4941 .0845 .046 Uiso calc R 1 . . H
H18B .0257 .5184 .1429 .046 Uiso calc R 1 . . H
C19 .1978(3) .51272(14) .2754(3) .0436(7) Uani d . 1 . . C
H19A .1335 .5131 .3463 .052 Uiso calc R 1 . . H
H19B .2336 .5606 .2636 .052 Uiso calc R 1 . . H
C20 .3249(3) .46461(14) .3054(3) .0388(7) Uani d . 1 . . C
H20A .3936 .4676 .2379 .047 Uiso calc R 1 . . H
H20B .3765 .4795 .3848 .047 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
C4 S1 C1 99.20(11) yes
C2 C1 S2 115.16(17) yes
C2 C1 S1 108.91(16) yes
S2 C1 S1 107.30(12) yes
C1 S2 C16 101.66(11) yes
C16 O2 C20 114.32(19) yes
O1 C2 C3 109.5(2) ?
O1 C2 C10 111.5(2) ?
C3 C2 C10 111.2(2) ?
O1 C2 C1 104.76(19) yes
C3 C2 C1 110.7(2) ?
C10 C2 C1 108.95(19) ?
C5 C4 C9 119.8(2) ?
C5 C4 S1 121.1(2) ?
C9 C4 S1 119.1(2) ?
C6 C5 C4 120.0(3) ?
C5 C6 C7 120.3(3) ?
C8 C7 C6 119.6(3) ?
C7 C8 C9 120.7(3) ?
C4 C9 C8 119.5(3) ?
C11 C10 C15 118.4(2) ?
C11 C10 C2 120.5(2) ?
C15 C10 C2 121.0(2) ?
C12 C11 C10 120.4(3) ?
C13 C12 C11 120.9(3) ?
C12 C13 C14 119.3(3) ?
C15 C14 C13 119.8(3) ?
C14 C15 C10 121.0(2) ?
O2 C16 C17 111.6(2) ?
O2 C16 S2 112.52(16) yes
C17 C16 S2 109.73(17) ?
C16 C17 C18 111.5(2) ?
C19 C18 C17 109.4(2) ?
C18 C19 C20 110.5(2) ?
O2 C20 C19 110.9(2) ?
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 C4 . 1.778(3) yes
S1 C1 . 1.831(2) yes
O1 C2 . 1.423(3) yes
C1 C2 . 1.546(3) yes
C1 S2 . 1.819(2) yes
S2 C16 . 1.828(2) yes
O2 C16 . 1.424(3) yes
O2 C20 . 1.431(3) yes
C2 C3 . 1.525(4) ?
C2 C10 . 1.531(3) ?
C4 C5 . 1.381(4) ?
C4 C9 . 1.383(4) ?
C5 C6 . 1.379(4) ?
C6 C7 . 1.380(4) ?
C7 C8 . 1.369(4) ?
C8 C9 . 1.385(4) ?
C10 C11 . 1.385(3) ?
C10 C15 . 1.386(3) ?
C11 C12 . 1.383(4) ?
C12 C13 . 1.367(4) ?
C13 C14 . 1.388(4) ?
C14 C15 . 1.383(4) ?
C16 C17 . 1.512(3) ?
C17 C18 . 1.525(4) ?
C18 C19 . 1.512(4) ?
C19 C20 . 1.515(4) ?
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
O1 H1A O2 4_565 .84 1.92 2.751(2) 167.7
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
C4 S1 C1 C2 -162.48(17) yes
C4 S1 C1 S2 72.25(15) yes
C2 C1 S2 C16 96.02(18) yes
S1 C1 S2 C16 -142.57(12) yes
S2 C1 C2 O1 66.0(2) yes
S1 C1 C2 O1 -54.5(2) yes
S2 C1 C2 C3 -176.06(17) yes
S1 C1 C2 C3 63.4(2) yes
S2 C1 C2 C10 -53.4(2) ?
S1 C1 C2 C10 -173.97(16) yes
C1 S1 C4 C5 70.4(2) ?
C1 S1 C4 C9 -111.0(2) ?
C9 C4 C5 C6 -.7(4) ?
S1 C4 C5 C6 177.9(2) ?
C4 C5 C6 C7 -.3(4) ?
C5 C6 C7 C8 .4(5) ?
C6 C7 C8 C9 .3(4) ?
C5 C4 C9 C8 1.5(4) ?
S1 C4 C9 C8 -177.1(2) ?
C7 C8 C9 C4 -1.3(4) ?
O1 C2 C10 C11 -19.1(3) ?
C3 C2 C10 C11 -141.6(2) ?
C1 C2 C10 C11 96.1(3) ?
O1 C2 C10 C15 165.3(2) ?
C3 C2 C10 C15 42.7(3) ?
C1 C2 C10 C15 -79.6(3) ?
C15 C10 C11 C12 1.8(4) ?
C2 C10 C11 C12 -173.9(2) ?
C10 C11 C12 C13 -1.5(4) ?
C11 C12 C13 C14 -.6(4) ?
C12 C13 C14 C15 2.2(4) ?
C13 C14 C15 C10 -1.9(4) ?
C11 C10 C15 C14 -.1(4) ?
C2 C10 C15 C14 175.6(2) ?
C20 O2 C16 C17 -55.7(3) ?
C20 O2 C16 S2 68.2(2) ?
C1 S2 C16 O2 67.04(18) yes
C1 S2 C16 C17 -168.11(18) ?
O2 C16 C17 C18 52.9(3) ?
S2 C16 C17 C18 -72.5(2) ?
C16 C17 C18 C19 -53.0(3) ?
C17 C18 C19 C20 54.6(3) ?
C16 O2 C20 C19 57.6(3) ?
C18 C19 C20 O2 -56.6(3) ?
