##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H24 O2 S2'
_chemical_formula_sum     'C20 H24 O2 S2'
_chemical_formula_iupac     'C20 H24 O2 S2'
_chemical_formula_weight     360.51
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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'
_cell_length_a     9.2440(18)
_cell_length_b     19.239(4)
_cell_length_c     10.682(2)
_cell_angle_alpha     90.00
_cell_angle_beta     93.37(3)
_cell_angle_gamma     90.00
_cell_volume     1896.5(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     4
_cell_measurement_theta_max     10
_cell_measurement_temperature     193(2)
_exptl_crystal_description     Prismatic
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max      .36
_exptl_crystal_size_mid      .30
_exptl_crystal_size_min      .25
_exptl_crystal_density_diffrn     1.263
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu      .290
_exptl_absorpt_correction_type     None
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-7S'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3637
_diffrn_reflns_av_R_equivalents      .0289
_diffrn_reflns_av_sigmaI/netI      .0541
_diffrn_reflns_theta_min     2.85
_diffrn_reflns_theta_max     25.25
_diffrn_reflns_theta_full     25.25
_diffrn_measured_fraction_theta_max      .964
_diffrn_measured_fraction_theta_full      .964
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     3
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <0.1
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR
and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and
is
 not relevant to the choice of reflections for refinement.  R-factors
based
 on F² are statistically about twice as large as those based on F, and
R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3418
_reflns_number_gt     2438
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .0780
_refine_ls_R_factor_gt      .0460
_refine_ls_wR_factor_ref      .1069
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     3418
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'w = 1/[σ²(Fo²)+(0.0501P)²+0.1099P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .277
_refine_diff_density_min      -.289
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'AFC-7S software'
_computing_cell_refinement     'AFC-7S software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXL97'
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_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  .0289(4)  .0361(4)  .0426(4)  -.0044(3)  .0115(3)  -.0118(3)
    O1  .0407(11)  .0316(10)  .0269(9)  -.0069(8)  .0051(8)  -.0079(7)
    C1  .0232(13)  .0273(13)  .0252(12)  .0006(11)  .0036(10)  -.0018(10)
    S2  .0316(4)  .0249(3)  .0253(3)  .0022(3)  .0036(3)  .0002(3)
    O2  .0419(11)  .0317(10)  .0263(9)  .0086(9)  .0011(8)  .0008(8)
    C2  .0286(14)  .0266(14)  .0266(13)  .0003(11)  .0026(11)  -.0027(10)
    C3  .0352(16)  .0291(15)  .0494(17)  .0053(12)  .0028(13)  -.0003(13)
    C4  .0226(13)  .0331(15)  .0408(15)  -.0034(11)  .0056(12)  -.0052(12)
    C5  .0343(15)  .0297(15)  .0438(16)  -.0028(12)  .0002(12)  .0025(12)
    C6  .0430(17)  .0411(17)  .0429(17)  -.0051(14)  -.0012(14)  -.0047(14)
    C7  .0336(16)  .0357(17)  .059(2)  -.0050(13)  .0040(14)  -.0177(14)
    C8  .0376(17)  .0299(15)  .063(2)  -.0031(13)  .0084(15)  .0021(14)
    C9  .0334(15)  .0349(16)  .0429(16)  -.0053(13)  .0080(12)  .0029(13)
    C10  .0279(13)  .0164(12)  .0300(13)  -.0019(10)  -.0011(11)  -.0042(10)
    C11  .0341(15)  .0342(15)  .0290(13)  -.0005(12)  -.0027(11)  -.0025(11)
    C12  .0286(15)  .0449(18)  .0509(18)  -.0024(13)  -.0087(13)  -.0026(14)
    C13  .0291(15)  .0401(17)  .0602(19)  -.0096(13)  .0091(14)  -.0063(15)
    C14  .0443(17)  .0285(15)  .0378(15)  -.0107(13)  .0109(13)  .0004(12)
    C15  .0329(14)  .0239(13)  .0316(14)  -.0033(11)  -.0011(11)  .0007(10)
    C16  .0310(14)  .0239(13)  .0299(13)  -.0015(11)  .0074(11)  .0009(10)
    C17  .0261(14)  .0385(16)  .0418(16)  .0026(13)  .0029(12)  -.0037(13)
    C18  .0357(16)  .0329(16)  .0456(16)  .0115(13)  .0012(13)  .0066(13)
    C19  .0459(18)  .0239(15)  .061(2)  .0025(13)  .0037(15)  -.0067(14)
    C20  .0420(17)  .0331(16)  .0402(16)  .0013(14)  -.0059(13)  -.0103(12)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are
taken
 into account individually in the estimation of esds in distances,
angles
 and torsion angles; correlations between esds in cell parameters are
only
 used when they are defined by crystal symmetry.  An approximate
(isotropic)
 treatment of cell esds is used for estimating esds involving l.s.
planes.
;
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_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
    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_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
    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) ?
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
data_diastereomer
_journal_date_recd_electronic     2001-02-06
_journal_date_accepted     2001-03-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      4
_journal_page_first     o335
_journal_page_last     o337
_journal_paper_category     EO
_publ_contact_author_name     'Jarno Kansikas'
_publ_contact_author_address
;
 Laboratory of Inorganic Chemistry, PO Box 55
 00014 University of Helsinki
 Finland
;
_publ_contact_author_email     jarno.kansikas@helsinki.fi
_publ_contact_author_fax     '358 9 191 50198'
_publ_contact_author_phone     '358 9 191 50202'
_publ_section_title
;
(1S*,2R*,2'R*)-2-Phenyl-1-phenylthio-1-(tetrahydropyran-2-ylthio)propan-2-ol
at 193 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Kansikas, Jarno'
;     Department of Chemistry
      Laboratory of Inorganic Chemistry
      PO Box 55
      00014 University of Helsinki
      Finland
;
    'Sipilä, Kaija'
;     Department of Chemistry
      Laboratory of Organic Chemistry
      PO Box 55
      00014 University of Helsinki
      Finland
;
