# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c



_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,3-bis((tert-butylsulfinyl)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 O2 S2'

_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_formula_weight         314.49



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'



_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14

_symmetry_space_group_name_hall  '-P 2ybc'


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                   12.443(2)

_cell_length_b                   6.5577(11)

_cell_length_c                   21.666(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 93.151(2)

_cell_angle_gamma                90.00

_cell_volume                     1765.2(5)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    2250

_cell_measurement_theta_min      2.43

_cell_measurement_theta_max      23.35



_exptl_crystal_description       block

_exptl_crystal_colour            blue

_exptl_crystal_size_max          0.26

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.15

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.183

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             680

_exptl_absorpt_coefficient_mu    0.301

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9258

_exptl_absorpt_correction_T_max  0.9562

_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      298(2)
_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            8800

_diffrn_reflns_av_R_equivalents  0.0281

_diffrn_reflns_av_sigmaI/netI    0.0332

_diffrn_reflns_limit_h_min       -14

_diffrn_reflns_limit_h_max       15

_diffrn_reflns_limit_k_min       -7

_diffrn_reflns_limit_k_max       7

_diffrn_reflns_limit_l_min       -26

_diffrn_reflns_limit_l_max       22

_diffrn_reflns_theta_min         1.88

_diffrn_reflns_theta_max         25.50

_reflns_number_total             3261

_reflns_number_gt                2311

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_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.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0762P)²+0.9899P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3261

_refine_ls_number_parameters     196

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0813

_refine_ls_R_factor_gt           0.0573

_refine_ls_wR_factor_ref         0.1645

_refine_ls_wR_factor_gt          0.1502

_refine_ls_goodness_of_fit_ref   1.062

_refine_ls_restrained_S_all      1.062

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



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















































S1 S 0.61344(7) 0.78918(13) 0.12989(4) 0.0573(3) Uani 1 1 d . . .
S2 S 0.99225(6) 0.21020(15) 0.14868(4) 0.0619(3) Uani 1 1 d . . .
O1 O 0.5195(3) 0.6733(5) 0.10893(18) 0.0874(10) Uani 0.80 1 d P . .
O1' O 0.6625(10) 0.6990(18) 0.1791(5) 0.071(3) Uani 0.20 1 d P . .
O2 O 0.9519(3) 0.0075(5) 0.13316(17) 0.1150(12) Uani 1 1 d . . .
C1 C 0.5017(3) 1.0277(6) 0.20148(17) 0.0752(10) Uani 1 1 d . . .
H1A H 0.5453 0.9775 0.2361 0.113 Uiso 1 1 calc R . .
H1B H 0.4448 0.9325 0.1914 0.113 Uiso 1 1 calc R . .
H1C H 0.4713 1.1570 0.2118 0.113 Uiso 1 1 calc R . .
C2 C 0.6686(3) 1.1854(6) 0.16219(18) 0.0723(10) Uani 1 1 d . . .
H2A H 0.6456 1.3126 0.1790 0.108 Uiso 1 1 calc R . .
H2B H 0.7068 1.2106 0.1257 0.108 Uiso 1 1 calc R . .
H2C H 0.7150 1.1164 0.1922 0.108 Uiso 1 1 calc R . .
C3 C 0.5043(3) 1.1371(6) 0.09082(16) 0.0681(9) Uani 1 1 d . . .
H3A H 0.4756 1.2679 0.1012 0.102 Uiso 1 1 calc R . .
H3B H 0.4462 1.0451 0.0802 0.102 Uiso 1 1 calc R . .
H3C H 0.5488 1.1513 0.0563 0.102 Uiso 1 1 calc R . .
C4 C 0.5710(2) 1.0535(5) 0.14591(14) 0.0511(7) Uani 1 1 d . . .
C5 C 0.6973(3) 0.8329(5) 0.06545(17) 0.0684(10) Uani 1 1 d . . .
H5A H 0.6543 0.8922 0.0313 0.082 Uiso 1 1 calc R . .
H5B H 0.7540 0.9286 0.0776 0.082 Uiso 1 1 calc R . .
C6 C 0.7459(3) 0.6380(5) 0.04508(14) 0.0536(8) Uani 1 1 d . . .
C7 C 0.6933(3) 0.5105(6) 0.00237(14) 0.0599(9) Uani 1 1 d . . .
H7 H 0.6248 0.5448 -0.0137 0.072 Uiso 1 1 calc R . .
C8 C 0.7410(3) 0.3341(6) -0.01643(14) 0.0619(9) Uani 1 1 d . . .
H8 H 0.7050 0.2509 -0.0455 0.074 Uiso 1 1 calc R . .
C9 C 0.8409(3) 0.2798(5) 0.00720(15) 0.0594(8) Uani 1 1 d . . .
H9 H 0.8725 0.1599 -0.0059 0.071 Uiso 1 1 calc R . .
C10 C 0.8955(2) 0.4017(5) 0.05044(14) 0.0526(8) Uani 1 1 d . . .
C11 C 0.8475(3) 0.5805(5) 0.06887(14) 0.0556(8) Uani 1 1 d . . .
H11 H 0.8840 0.6638 0.0977 0.067 Uiso 1 1 calc R . .
C12 C 1.0052(3) 0.3435(6) 0.07750(16) 0.0702(10) Uani 1 1 d . . .
H12A H 1.0484 0.4652 0.0848 0.084 Uiso 1 1 calc R . .
H12B H 1.0411 0.2574 0.0487 0.084 Uiso 1 1 calc R . .
C13 C 1.1348(3) 0.1867(6) 0.17628(15) 0.0616(9) Uani 1 1 d . . .
C14 C 1.1790(4) 0.3976(9) 0.1874(3) 0.128(2) Uani 1 1 d . . .
H14A H 1.2427 0.3901 0.2144 0.192 Uiso 1 1 calc R . .
H14B H 1.1261 0.4801 0.2062 0.192 Uiso 1 1 calc R . .
H14C H 1.1964 0.4573 0.1488 0.192 Uiso 1 1 calc R . .
C15 C 1.1300(4) 0.0741(10) 0.2368(2) 0.121(2) Uani 1 1 d . . .
H15A H 1.0907 -0.0507 0.2303 0.182 Uiso 1 1 calc R . .
H15B H 1.0945 0.1575 0.2659 0.182 Uiso 1 1 calc R . .
H15C H 1.2017 0.0440 0.2527 0.182 Uiso 1 1 calc R . .
C16 C 1.1954(4) 0.0691(10) 0.1305(2) 0.123(2) Uani 1 1 d . . .
H16A H 1.2142 0.1579 0.0975 0.185 Uiso 1 1 calc R . .
H16B H 1.1512 -0.0401 0.1139 0.185 Uiso 1 1 calc R . .
H16C H 1.2597 0.0140 0.1505 0.185 Uiso 1 1 calc R . .



loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12





















S1 0.0672(5) 0.0365(4) 0.0685(5) 0.0072(4) 0.0067(4) 0.0031(4)
S2 0.0519(5) 0.0734(6) 0.0602(5) 0.0120(4) 0.0017(4) -0.0049(4)
O1 0.083(2) 0.051(2) 0.128(3) -0.0172(19) 0.011(2) -0.0176(16)
O1' 0.087(8) 0.063(8) 0.062(7) 0.024(6) -0.003(6) 0.026(6)
O2 0.107(2) 0.075(2) 0.157(3) 0.026(2) -0.052(2) -0.0375(18)
C1 0.084(3) 0.069(3) 0.074(2) 0.001(2) 0.0143(19) 0.013(2)
C2 0.077(2) 0.052(2) 0.086(2) -0.0087(19) -0.0111(19) -0.0087(18)
C3 0.072(2) 0.056(2) 0.075(2) 0.0089(18) -0.0104(18) 0.0128(18)
C4 0.0557(18) 0.0380(17) 0.0588(18) 0.0009(14) -0.0051(14) 0.0036(14)
C5 0.088(3) 0.045(2) 0.073(2) 0.0111(17) 0.0140(19) 0.0103(18)
C6 0.069(2) 0.0418(17) 0.0510(17) 0.0082(14) 0.0075(15) 0.0025(15)
C7 0.062(2) 0.061(2) 0.0559(19) 0.0106(17) -0.0032(15) 0.0044(17)
C8 0.072(2) 0.060(2) 0.0519(18) -0.0038(16) -0.0045(16) -0.0035(18)
C9 0.070(2) 0.052(2) 0.0572(18) 0.0017(16) 0.0101(16) 0.0075(17)
C10 0.0524(17) 0.057(2) 0.0488(17) 0.0121(15) 0.0058(13) 0.0013(15)
C11 0.063(2) 0.054(2) 0.0493(17) 0.0053(14) 0.0011(14) -0.0122(16)
C12 0.0530(19) 0.088(3) 0.070(2) 0.022(2) 0.0061(16) 0.0014(18)
C13 0.0521(18) 0.076(3) 0.0555(19) 0.0004(17) -0.0054(14) -0.0008(17)
C14 0.118(4) 0.110(4) 0.149(5) -0.015(4) -0.055(3) -0.037(3)
C15 0.100(3) 0.175(6) 0.087(3) 0.046(3) -0.021(3) 0.004(4)
C16 0.077(3) 0.188(6) 0.104(3) -0.026(4) -0.005(2) 0.058(3)



_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_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag















































S1 O1' 1.337(10) . ?
S1 O1 1.446(3) . ?
S1 C5 1.811(4) . ?
S1 C4 1.850(3) . ?
S2 O2 1.454(3) . ?
S2 C12 1.788(3) . ?
S2 C13 1.846(3) . ?
C1 C4 1.529(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.516(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C5 C6 1.491(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.385(5) . ?
C6 C11 1.391(4) . ?
C7 C8 1.372(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 C12 1.505(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.494(6) . ?
C13 C14 1.503(6) . ?
C13 C15 1.509(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?



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























































































O1' S1 O1 110.1(6) . . ?
O1' S1 C5 115.3(5) . . ?
O1 S1 C5 109.3(2) . . ?
O1' S1 C4 112.8(5) . . ?
O1 S1 C4 108.49(17) . . ?
C5 S1 C4 100.29(15) . . ?
O2 S2 C12 107.1(2) . . ?
O2 S2 C13 108.16(18) . . ?
C12 S2 C13 100.95(15) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C3 111.9(3) . . ?
C2 C4 C1 111.0(3) . . ?
C3 C4 C1 110.5(3) . . ?
C2 C4 S1 110.2(2) . . ?
C3 C4 S1 109.9(2) . . ?
C1 C4 S1 102.9(2) . . ?
C6 C5 S1 110.7(2) . . ?
C6 C5 H5A 109.5 . . ?
S1 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
S1 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C11 118.1(3) . . ?
C7 C6 C5 122.0(3) . . ?
C11 C6 C5 119.9(3) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 C12 121.2(3) . . ?
C11 C10 C12 119.9(3) . . ?
C10 C11 C6 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C10 C12 S2 109.7(2) . . ?
C10 C12 H12A 109.7 . . ?
S2 C12 H12A 109.7 . . ?
C10 C12 H12B 109.7 . . ?
S2 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C16 C13 C14 112.8(4) . . ?
C16 C13 C15 111.7(4) . . ?
C14 C13 C15 110.0(4) . . ?
C16 C13 S2 109.8(3) . . ?
C14 C13 S2 108.2(3) . . ?
C15 C13 S2 103.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?



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_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag


































O1' S1 C4 C2 63.1(7) . . . . ?
O1 S1 C4 C2 -174.6(3) . . . . ?
C5 S1 C4 C2 -60.1(3) . . . . ?
O1' S1 C4 C3 -173.1(6) . . . . ?
O1 S1 C4 C3 -50.9(3) . . . . ?
C5 S1 C4 C3 63.7(3) . . . . ?
O1' S1 C4 C1 -55.4(6) . . . . ?
O1 S1 C4 C1 66.9(3) . . . . ?
C5 S1 C4 C1 -178.6(2) . . . . ?
O1' S1 C5 C6 56.3(7) . . . . ?
O1 S1 C5 C6 -68.3(3) . . . . ?
C4 S1 C5 C6 177.7(3) . . . . ?
S1 C5 C6 C7 87.2(3) . . . . ?
S1 C5 C6 C11 -93.3(3) . . . . ?
C11 C6 C7 C8 -0.9(5) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C8 C9 C10 C12 179.4(3) . . . . ?
C9 C10 C11 C6 0.5(4) . . . . ?
C12 C10 C11 C6 -179.5(3) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C5 C6 C11 C10 -179.3(3) . . . . ?
C9 C10 C12 S2 -94.5(3) . . . . ?
C11 C10 C12 S2 85.5(3) . . . . ?
O2 S2 C12 C10 73.8(3) . . . . ?
C13 S2 C12 C10 -173.2(3) . . . . ?
O2 S2 C13 C16 52.0(4) . . . . ?
C12 S2 C13 C16 -60.3(4) . . . . ?
O2 S2 C13 C14 175.5(3) . . . . ?
C12 S2 C13 C14 63.2(4) . . . . ?
O2 S2 C13 C15 -67.7(4) . . . . ?
C12 S2 C13 C15 -179.9(3) . . . . ?



_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        25.50

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.944

_refine_diff_density_min         -0.432

_refine_diff_density_rms         0.050

_database_code_depnum_ccdc_archive 'CCDC 755513'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c



_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,2-bis((tert-butylthio)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 S2'

_chemical_formula_sum            'C16 H26 S2'

_chemical_formula_weight         282.51

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2

_symmetry_space_group_name_hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2584(14)
_cell_length_b                   10.6118(18)
_cell_length_c                   11.751(2)
_cell_angle_alpha                67.631(2)
_cell_angle_beta                 72.609(2)
_cell_angle_gamma                69.331(2)
_cell_volume                     874.8(3)
_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1626

_cell_measurement_theta_min      2.25

_cell_measurement_theta_max      18.11



_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.072

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             308

_exptl_absorpt_coefficient_mu    0.289

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5122
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3723
_reflns_number_gt                2532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.1450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.9541(4) 0.1593(3) 0.0503(3) 0.0828(8) Uani 1 1 d . . .
H1 H 1.0414 0.0819 0.0320 0.099 Uiso 1 1 calc R . .
C2 C 0.8122(3) 0.1385(3) 0.1465(3) 0.0704(7) Uani 1 1 d . . .
H2 H 0.8045 0.0467 0.1918 0.085 Uiso 1 1 calc R . .
C3 C 0.6801(3) 0.2521(2) 0.1772(2) 0.0524(5) Uani 1 1 d . . .
C4 C 0.6931(3) 0.3894(2) 0.10527(19) 0.0496(5) Uani 1 1 d . . .
C5 C 0.8367(3) 0.4073(3) 0.0088(2) 0.0634(6) Uani 1 1 d . . .
H5 H 0.8454 0.4983 -0.0388 0.076 Uiso 1 1 calc R . .
C6 C 0.9668(4) 0.2927(3) -0.0179(3) 0.0791(8) Uani 1 1 d . . .
H6 H 1.0630 0.3066 -0.0824 0.095 Uiso 1 1 calc R . .
C7 C 0.5328(3) 0.2259(3) 0.2863(2) 0.0628(6) Uani 1 1 d . . .
H7A H 0.4934 0.3012 0.3240 0.075 Uiso 1 1 calc R . .
H7B H 0.5741 0.1372 0.3490 0.075 Uiso 1 1 calc R . .
C8 C 0.5578(3) 0.5182(2) 0.1317(2) 0.0575(6) Uani 1 1 d . . .
H8A H 0.4419 0.5016 0.1607 0.069 Uiso 1 1 calc R . .
H8B H 0.5551 0.5983 0.0557 0.069 Uiso 1 1 calc R . .
C9 C 0.1660(3) 0.2348(2) 0.3676(2) 0.0550(5) Uani 1 1 d . . .
C10 C 0.2130(4) 0.1211(3) 0.4878(2) 0.0791(8) Uani 1 1 d . . .
H10A H 0.1124 0.1272 0.5546 0.119 Uiso 1 1 calc R . .
H10B H 0.3086 0.1346 0.5083 0.119 Uiso 1 1 calc R . .
H10C H 0.2477 0.0296 0.4765 0.119 Uiso 1 1 calc R . .
C11 C 0.0178(4) 0.2129(3) 0.3321(3) 0.0856(8) Uani 1 1 d . . .
H11A H 0.0525 0.1198 0.3240 0.128 Uiso 1 1 calc R . .
H11B H -0.0067 0.2823 0.2537 0.128 Uiso 1 1 calc R . .
H11C H -0.0860 0.2227 0.3960 0.128 Uiso 1 1 calc R . .
C12 C 0.1134(4) 0.3822(3) 0.3808(3) 0.0884(9) Uani 1 1 d . . .
H12A H 0.0848 0.4520 0.3035 0.133 Uiso 1 1 calc R . .
H12B H 0.2096 0.3961 0.4001 0.133 Uiso 1 1 calc R . .
H12C H 0.0125 0.3912 0.4470 0.133 Uiso 1 1 calc R . .
C13 C 0.4642(4) 0.7290(3) 0.2551(2) 0.0696(7) Uani 1 1 d . . .
C14 C 0.5133(7) 0.7597(4) 0.3550(4) 0.1504(18) Uani 1 1 d . . .
H14A H 0.4368 0.8483 0.3655 0.226 Uiso 1 1 calc R . .
H14B H 0.6333 0.7648 0.3295 0.226 Uiso 1 1 calc R . .
H14C H 0.5009 0.6854 0.4329 0.226 Uiso 1 1 calc R . .
C15 C 0.2755(5) 0.7253(4) 0.2901(5) 0.1392(17) Uani 1 1 d . . .
H15A H 0.2005 0.8144 0.3005 0.209 Uiso 1 1 calc R . .
H15B H 0.2587 0.6509 0.3672 0.209 Uiso 1 1 calc R . .
H15C H 0.2464 0.7083 0.2250 0.209 Uiso 1 1 calc R . .
C16 C 0.4919(5) 0.8411(3) 0.1302(3) 0.1176(13) Uani 1 1 d . . .
H16A H 0.4645 0.8189 0.0673 0.176 Uiso 1 1 calc R . .
H16B H 0.6125 0.8441 0.1074 0.176 Uiso 1 1 calc R . .
H16C H 0.4161 0.9317 0.1364 0.176 Uiso 1 1 calc R . .
S1 S 0.35049(8) 0.21847(6) 0.23528(5) 0.05675(19) Uani 1 1 d . . .
S2 S 0.61431(9) 0.55599(6) 0.25084(6) 0.0662(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0603(16) 0.096(2) 0.111(2) -0.0677(19) -0.0122(16) -0.0074(15)
C2 0.0680(16) 0.0598(14) 0.0943(19) -0.0298(14) -0.0239(14) -0.0162(12)
C3 0.0481(12) 0.0596(13) 0.0563(13) -0.0190(10) -0.0149(10) -0.0172(10)
C4 0.0485(12) 0.0602(13) 0.0475(12) -0.0201(10) -0.0140(9) -0.0156(10)
C5 0.0641(15) 0.0759(16) 0.0570(14) -0.0229(12) -0.0047(11) -0.0295(13)
C6 0.0617(16) 0.108(2) 0.0799(19) -0.0506(17) 0.0064(13) -0.0299(16)
C7 0.0605(14) 0.0746(15) 0.0542(13) -0.0075(11) -0.0170(11) -0.0275(12)
C8 0.0616(14) 0.0602(13) 0.0549(13) -0.0187(10) -0.0204(11) -0.0127(11)
C9 0.0548(13) 0.0585(13) 0.0540(13) -0.0146(10) -0.0089(10) -0.0221(10)
C10 0.0807(18) 0.0897(19) 0.0597(15) -0.0062(13) -0.0124(13) -0.0339(15)
C11 0.0605(16) 0.113(2) 0.091(2) -0.0282(17) -0.0144(14) -0.0366(16)
C12 0.085(2) 0.0765(18) 0.100(2) -0.0398(16) 0.0067(16) -0.0234(15)
C13 0.0767(17) 0.0626(15) 0.0680(16) -0.0289(13) -0.0028(13) -0.0168(13)
C14 0.230(5) 0.108(3) 0.152(4) -0.085(3) -0.085(4) -0.001(3)
C15 0.086(3) 0.119(3) 0.203(5) -0.090(3) 0.033(3) -0.022(2)
C16 0.147(3) 0.0632(18) 0.105(3) -0.0172(17) 0.004(2) -0.018(2)
S1 0.0574(3) 0.0661(4) 0.0544(3) -0.0196(3) -0.0106(2) -0.0246(3)
S2 0.0796(4) 0.0609(4) 0.0672(4) -0.0261(3) -0.0298(3) -0.0093(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.359(4) . ?
C1 C2 1.379(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(3) . ?
C3 C7 1.495(3) . ?
C4 C5 1.385(3) . ?
C4 C8 1.500(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 S1 1.814(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 S2 1.814(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.517(3) . ?
C9 C11 1.519(3) . ?
C9 C12 1.524(3) . ?
C9 S1 1.836(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C15 1.499(4) . ?
C13 C16 1.512(4) . ?
C13 C14 1.522(4) . ?
C13 S2 1.826(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C7 120.1(2) . . ?
C4 C3 C7 121.8(2) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 C8 118.8(2) . . ?
C3 C4 C8 121.88(19) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C3 C7 S1 110.13(15) . . ?
C3 C7 H7A 109.6 . . ?
S1 C7 H7A 109.6 . . ?
C3 C7 H7B 109.6 . . ?
S1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C4 C8 S2 108.83(14) . . ?
C4 C8 H8A 109.9 . . ?
S2 C8 H8A 109.9 . . ?
C4 C8 H8B 109.9 . . ?
S2 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C11 110.1(2) . . ?
C10 C9 C12 111.2(2) . . ?
C11 C9 C12 110.2(2) . . ?
C10 C9 S1 110.72(17) . . ?
C11 C9 S1 104.12(16) . . ?
C12 C9 S1 110.27(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C16 109.1(3) . . ?
C15 C13 C14 110.8(3) . . ?
C16 C13 C14 110.2(3) . . ?
C15 C13 S2 111.4(2) . . ?
C16 C13 S2 111.22(19) . . ?
C14 C13 S2 104.0(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 S1 C9 103.63(11) . . ?
C8 S2 C13 104.49(11) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C2 C3 C7 -176.8(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C7 C3 C4 C5 177.1(2) . . . . ?
C2 C3 C4 C8 -179.69(19) . . . . ?
C7 C3 C4 C8 -1.4(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C8 C4 C5 C6 178.6(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C2 C3 C7 S1 -90.9(2) . . . . ?
C4 C3 C7 S1 90.9(2) . . . . ?
C5 C4 C8 S2 -92.8(2) . . . . ?
C3 C4 C8 S2 85.7(2) . . . . ?
C3 C7 S1 C9 -165.17(16) . . . . ?
C10 C9 S1 C7 -55.79(19) . . . . ?
C11 C9 S1 C7 -174.14(17) . . . . ?
C12 C9 S1 C7 67.6(2) . . . . ?
C4 C8 S2 C13 170.70(16) . . . . ?
C15 C13 S2 C8 60.8(3) . . . . ?
C16 C13 S2 C8 -61.2(3) . . . . ?
C14 C13 S2 C8 -179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 755514'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
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data_a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,2-bis((tert-butylsulfinyl)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 O2 S2'
_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           orthorhombic

_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4014(17)
_cell_length_b                   11.1506(18)
_cell_length_c                   15.433(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1790.0(5)
_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    980

_cell_measurement_theta_min      2.25

_cell_measurement_theta_max      18.11



_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             680.0

_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10956
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.26
_reflns_number_total             4144
_reflns_number_gt                2018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(8)
_refine_ls_number_reflns         4144
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3559(4) 0.6732(3) 0.8981(2) 0.0898(13) Uani 1 1 d . . .
H1A H 0.3471 0.7589 0.8978 0.135 Uiso 1 1 calc R . .
H1B H 0.2891 0.6387 0.9330 0.135 Uiso 1 1 calc R . .
H1C H 0.3492 0.6434 0.8399 0.135 Uiso 1 1 calc R . .
C2 C 0.4858(4) 0.6396(3) 0.9353(2) 0.0625(11) Uani 1 1 d . . .
C3 C 0.5029(4) 0.6984(3) 1.0244(2) 0.1037(16) Uani 1 1 d . . .
H3A H 0.5814 0.6708 1.0502 0.156 Uiso 1 1 calc R . .
H3B H 0.4317 0.6772 1.0610 0.156 Uiso 1 1 calc R . .
H3C H 0.5060 0.7839 1.0177 0.156 Uiso 1 1 calc R . .
C4 C 0.5978(3) 0.6682(3) 0.8767(2) 0.0798(13) Uani 1 1 d . . .
H4A H 0.5839 0.6324 0.8209 0.120 Uiso 1 1 calc R . .
H4B H 0.6755 0.6369 0.9015 0.120 Uiso 1 1 calc R . .
H4C H 0.6053 0.7536 0.8704 0.120 Uiso 1 1 calc R . .
C5 C 0.0252(4) 0.4964(3) 0.8710(2) 0.1107(16) Uani 1 1 d . . .
H5A H 0.0812 0.5396 0.8327 0.166 Uiso 1 1 calc R . .
H5B H 0.0681 0.4832 0.9253 0.166 Uiso 1 1 calc R . .
H5C H -0.0516 0.5422 0.8807 0.166 Uiso 1 1 calc R . .
C6 C -0.0922(3) 0.3957(3) 0.7505(2) 0.0821(13) Uani 1 1 d . . .
H6A H -0.1680 0.4399 0.7661 0.123 Uiso 1 1 calc R . .
H6B H -0.1166 0.3194 0.7268 0.123 Uiso 1 1 calc R . .
H6C H -0.0442 0.4400 0.7081 0.123 Uiso 1 1 calc R . .
C7 C -0.0097(3) 0.3762(3) 0.8306(2) 0.0572(10) Uani 1 1 d . . .
C8 C -0.0771(3) 0.2951(4) 0.8949(2) 0.1047(15) Uani 1 1 d . . .
H8A H -0.0282 0.2918 0.9476 0.157 Uiso 1 1 calc R . .
H8B H -0.0845 0.2160 0.8710 0.157 Uiso 1 1 calc R . .
H8C H -0.1613 0.3262 0.9069 0.157 Uiso 1 1 calc R . .
C9 C 0.2243(3) 0.2813(3) 0.88990(18) 0.0499(9) Uani 1 1 d . . .
H9A H 0.2405 0.3590 0.9159 0.060 Uiso 1 1 calc R . .
H9B H 0.1731 0.2346 0.9302 0.060 Uiso 1 1 calc R . .
C10 C 0.4687(3) 0.4144(2) 0.85249(17) 0.0526(9) Uani 1 1 d . . .
H10A H 0.3920 0.4440 0.8239 0.063 Uiso 1 1 calc R . .
H10B H 0.5428 0.4387 0.8186 0.063 Uiso 1 1 calc R . .
C11 C 0.4637(3) 0.2794(3) 0.85832(19) 0.0466(9) Uani 1 1 d . . .
C12 C 0.3504(3) 0.2184(3) 0.87397(18) 0.0428(8) Uani 1 1 d . . .
C13 C 0.3531(4) 0.0936(3) 0.8784(2) 0.0557(10) Uani 1 1 d . . .
H13 H 0.2776 0.0514 0.8891 0.067 Uiso 1 1 calc R . .
C14 C 0.4659(4) 0.0327(3) 0.8670(2) 0.0730(12) Uani 1 1 d . . .
H14 H 0.4660 -0.0506 0.8691 0.088 Uiso 1 1 calc R . .
C15 C 0.5783(4) 0.0923(4) 0.8528(2) 0.0716(12) Uani 1 1 d . . .
H15 H 0.6548 0.0502 0.8459 0.086 Uiso 1 1 calc R . .
C16 C 0.5769(3) 0.2161(4) 0.8489(2) 0.0638(11) Uani 1 1 d . . .
H16 H 0.6534 0.2574 0.8398 0.077 Uiso 1 1 calc R . .
O1 O 0.2080(2) 0.3905(2) 0.73778(14) 0.0833(9) Uani 1 1 d . . .
O2 O 0.6078(3) 0.44475(19) 0.99340(16) 0.0966(10) Uani 1 1 d . . .
S1 S 0.13575(9) 0.30104(8) 0.78999(6) 0.0560(3) Uani 1 1 d . . .
S2 S 0.47952(10) 0.47741(7) 0.96055(6) 0.0608(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.091(3) 0.058(3) 0.121(3) 0.002(3) -0.018(3) 0.005(3)
C2 0.078(3) 0.040(2) 0.070(3) 0.0022(19) -0.015(2) -0.006(2)
C3 0.164(5) 0.066(3) 0.082(3) -0.021(2) -0.028(3) -0.029(3)
C4 0.081(3) 0.055(3) 0.104(3) 0.011(2) 0.002(3) -0.018(2)
C5 0.085(3) 0.104(3) 0.143(4) -0.056(3) -0.022(3) 0.036(3)
C6 0.067(3) 0.102(3) 0.077(3) 0.009(2) -0.014(2) 0.008(2)
C7 0.041(3) 0.074(3) 0.057(2) -0.003(2) -0.009(2) 0.006(2)
C8 0.052(3) 0.176(5) 0.086(3) 0.043(3) 0.015(2) 0.010(3)
C9 0.052(2) 0.056(2) 0.0417(19) 0.0042(19) 0.0047(17) -0.0047(19)
C10 0.061(3) 0.049(2) 0.048(2) 0.0020(17) -0.0032(19) -0.0125(19)
C11 0.049(2) 0.044(2) 0.047(2) -0.0018(18) -0.0048(18) -0.002(2)
C12 0.045(2) 0.045(2) 0.0385(19) 0.0003(17) 0.0008(18) -0.0012(19)
C13 0.067(3) 0.042(2) 0.059(2) -0.0013(19) 0.001(2) -0.002(2)
C14 0.103(4) 0.049(2) 0.067(3) -0.009(2) 0.004(3) 0.015(3)
C15 0.067(3) 0.071(3) 0.077(3) -0.010(3) -0.004(2) 0.024(2)
C16 0.052(3) 0.065(3) 0.075(3) -0.008(2) -0.001(2) -0.004(2)
O1 0.065(2) 0.120(2) 0.0645(16) 0.0334(15) 0.0074(14) -0.0108(16)
O2 0.108(3) 0.0663(18) 0.115(2) 0.0118(16) -0.0608(19) -0.0017(16)
S1 0.0539(6) 0.0655(6) 0.0485(5) -0.0026(5) -0.0013(5) -0.0002(5)
S2 0.0815(8) 0.0453(5) 0.0557(6) 0.0030(5) -0.0167(6) -0.0073(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.516(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.509(4) . ?
C2 C3 1.533(4) . ?
C2 S2 1.851(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C7 1.522(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.520(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.515(4) . ?
C7 S1 1.840(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C12 1.507(4) . ?
C9 S1 1.810(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(4) . ?
C10 S2 1.813(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.381(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O1 S1 1.487(2) . ?
O2 S2 1.473(2) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 C1 114.1(3) . . ?
C4 C2 C3 111.0(3) . . ?
C1 C2 C3 109.7(3) . . ?
C4 C2 S2 111.1(2) . . ?
C1 C2 S2 106.9(2) . . ?
C3 C2 S2 103.5(2) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C5 H5A 109.5 . . ?
C7 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C7 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C6 110.0(3) . . ?
C5 C7 C8 111.5(3) . . ?
C6 C7 C8 110.9(3) . . ?
C5 C7 S1 110.1(3) . . ?
C6 C7 S1 104.6(2) . . ?
C8 C7 S1 109.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C9 S1 111.1(2) . . ?
C12 C9 H9A 109.4 . . ?
S1 C9 H9A 109.4 . . ?
C12 C9 H9B 109.4 . . ?
S1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 S2 109.51(19) . . ?
C11 C10 H10A 109.8 . . ?
S2 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
S2 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 119.6(3) . . ?
C16 C11 C10 118.3(3) . . ?
C12 C11 C10 122.1(3) . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 C9 122.8(3) . . ?
C13 C12 C9 118.3(3) . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.0(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O1 S1 C9 106.63(14) . . ?
O1 S1 C7 107.11(16) . . ?
C9 S1 C7 100.60(14) . . ?
O2 S2 C10 106.08(15) . . ?
O2 S2 C2 106.36(16) . . ?
C10 S2 C2 100.80(14) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C10 C11 C16 -95.8(3) . . . . ?
S2 C10 C11 C12 83.2(3) . . . . ?
C16 C11 C12 C13 -1.1(5) . . . . ?
C10 C11 C12 C13 179.9(3) . . . . ?
C16 C11 C12 C9 176.5(3) . . . . ?
C10 C11 C12 C9 -2.5(5) . . . . ?
S1 C9 C12 C11 92.2(3) . . . . ?
S1 C9 C12 C13 -90.2(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C9 C12 C13 C14 -178.0(3) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C12 C11 C16 C15 1.5(5) . . . . ?
C10 C11 C16 C15 -179.4(3) . . . . ?
C12 C9 S1 O1 -69.1(3) . . . . ?
C12 C9 S1 C7 179.3(2) . . . . ?
C5 C7 S1 O1 -48.8(3) . . . . ?
C6 C7 S1 O1 69.4(3) . . . . ?
C8 C7 S1 O1 -171.7(2) . . . . ?
C5 C7 S1 C9 62.4(3) . . . . ?
C6 C7 S1 C9 -179.4(2) . . . . ?
C8 C7 S1 C9 -60.5(3) . . . . ?
C11 C10 S2 O2 68.7(3) . . . . ?
C11 C10 S2 C2 179.4(2) . . . . ?
C4 C2 S2 O2 52.7(3) . . . . ?
C1 C2 S2 O2 177.8(3) . . . . ?
C3 C2 S2 O2 -66.4(3) . . . . ?
C4 C2 S2 C10 -57.8(3) . . . . ?
C1 C2 S2 C10 67.3(3) . . . . ?
C3 C2 S2 C10 -176.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 755515'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c


_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,4-bis((tert-butylsulfinyl)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 O2 S2'

_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_formula_weight         314.51



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'



_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14

_symmetry_space_group_name_hall  '-P 2ybc'

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                   5.985(4)

_cell_length_b                   10.346(7)

_cell_length_c                   27.985(18)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.592(9)

_cell_angle_gamma                90.00

_cell_volume                     1733(2)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1150

_cell_measurement_theta_min      2.91

_cell_measurement_theta_max      19.56



_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             680

_exptl_absorpt_coefficient_mu    0.307

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            9885

_diffrn_reflns_av_R_equivalents  0.0632

_diffrn_reflns_av_sigmaI/netI    0.1158

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -36

_diffrn_reflns_limit_l_max       36

_diffrn_reflns_theta_min         2.10

_diffrn_reflns_theta_max         27.87

_reflns_number_total             3899

_reflns_number_gt                2080

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_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.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1293P)²+5.1167P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     SHELXL

_refine_ls_extinction_coef       0.025(5)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         3899

_refine_ls_number_parameters     188

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1749

_refine_ls_R_factor_gt           0.1103

_refine_ls_wR_factor_ref         0.3307

_refine_ls_wR_factor_gt          0.2965

_refine_ls_goodness_of_fit_ref   1.025

_refine_ls_restrained_S_all      1.025

_refine_ls_shift/su_max          0.004

_refine_ls_shift/su_mean         0.001



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
C1 C 0.1962(17) 0.2753(8) 0.4084(3) 0.082(3) Uani 1 1 d . . .
H1A H 0.2829 0.3522 0.4136 0.123 Uiso 1 1 calc R . .
H1B H 0.0426 0.2922 0.4156 0.123 Uiso 1 1 calc R . .
H1C H 0.2080 0.2493 0.3756 0.123 Uiso 1 1 calc R . .
C2 C 0.1576(15) 0.0442(8) 0.4303(3) 0.075(2) Uani 1 1 d . . .
H2A H 0.0046 0.0534 0.4397 0.112 Uiso 1 1 calc R . .
H2B H 0.2262 -0.0245 0.4483 0.112 Uiso 1 1 calc R . .
H2C H 0.1633 0.0243 0.3968 0.112 Uiso 1 1 calc R . .
C3 C 0.2822(11) 0.1698(7) 0.4399(2) 0.0539(16) Uani 1 1 d . . .
C4 C 0.5248(14) 0.1437(11) 0.4347(4) 0.096(3) Uani 1 1 d . . .
H4A H 0.5553 0.1210 0.4021 0.144 Uiso 1 1 calc R . .
H4B H 0.5676 0.0735 0.4553 0.144 Uiso 1 1 calc R . .
H4C H 0.6083 0.2196 0.4433 0.144 Uiso 1 1 calc R . .
C5 C 0.3858(14) 0.3554(7) 0.5094(2) 0.068(2) Uani 1 1 d . . .
H5A H 0.5317 0.3449 0.4952 0.082 Uiso 1 1 calc R . .
H5B H 0.3089 0.4251 0.4929 0.082 Uiso 1 1 calc R . .
C6 C 0.4127(12) 0.3890(7) 0.5617(2) 0.0579(17) Uani 1 1 d . . .
C7 C 0.2541(13) 0.4553(7) 0.5853(3) 0.0639(19) Uani 1 1 d . . .
H7 H 0.1259 0.4813 0.5689 0.077 Uiso 1 1 calc R . .
C8 C 0.2769(12) 0.4855(7) 0.6330(2) 0.0577(17) Uani 1 1 d . . .
H8 H 0.1653 0.5319 0.6483 0.069 Uiso 1 1 calc R . .
C9 C 0.4676(11) 0.4464(6) 0.6588(2) 0.0527(16) Uani 1 1 d . . .
C10 C 0.6294(13) 0.3800(7) 0.6343(3) 0.0639(19) Uani 1 1 d . . .
H10 H 0.7585 0.3541 0.6504 0.077 Uiso 1 1 calc R . .
C11 C 0.6049(13) 0.3512(7) 0.5867(3) 0.0651(19) Uani 1 1 d . . .
H11 H 0.7169 0.3063 0.5709 0.078 Uiso 1 1 calc R . .
C12 C 0.4910(13) 0.4730(8) 0.7105(2) 0.0660(19) Uani 1 1 d . . .
H12A H 0.5213 0.3926 0.7272 0.079 Uiso 1 1 calc R . .
H12B H 0.3509 0.5070 0.7223 0.079 Uiso 1 1 calc R . .
C13 C 0.5409(14) 0.5622(9) 0.8152(3) 0.080(2) Uani 1 1 d . . .
H13A H 0.4612 0.4821 0.8122 0.120 Uiso 1 1 calc R . .
H13B H 0.4514 0.6311 0.8023 0.120 Uiso 1 1 calc R . .
H13C H 0.5725 0.5789 0.8484 0.120 Uiso 1 1 calc R . .
C14 C 0.7562(12) 0.5537(7) 0.7884(2) 0.0569(17) Uani 1 1 d . . .
C15 C 0.8648(16) 0.4224(8) 0.7930(3) 0.085(3) Uani 1 1 d . . .
H15A H 0.9847 0.4156 0.7706 0.127 Uiso 1 1 calc R . .
H15B H 0.7561 0.3563 0.7865 0.127 Uiso 1 1 calc R . .
H15C H 0.9228 0.4119 0.8249 0.127 Uiso 1 1 calc R . .
C16 C 0.9194(14) 0.6599(8) 0.8036(3) 0.077(2) Uani 1 1 d . . .
H16A H 0.9687 0.6445 0.8359 0.115 Uiso 1 1 calc R . .
H16B H 0.8461 0.7423 0.8018 0.115 Uiso 1 1 calc R . .
H16C H 1.0459 0.6596 0.7828 0.115 Uiso 1 1 calc R . .
O1 O -0.0105(11) 0.2466(7) 0.5062(2) 0.101(2) Uani 1 1 d . . .
O2 O 0.6108(12) 0.7169(6) 0.7198(2) 0.097(2) Uani 1 1 d . . .
S1 S 0.7109(3) 0.58636(17) 0.72399(6) 0.0584(6) Uani 1 1 d . . .
S2 S 0.2275(3) 0.20726(17) 0.50297(6) 0.0594(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.121(8) 0.071(5) 0.054(4) -0.002(4) -0.009(4) 0.002(5)
C2 0.082(6) 0.069(5) 0.073(5) -0.014(4) 0.007(4) -0.012(4)
C3 0.051(4) 0.061(4) 0.049(3) -0.005(3) -0.004(3) -0.006(3)
C4 0.059(5) 0.117(8) 0.112(7) -0.029(6) 0.009(5) 0.011(5)
C5 0.088(6) 0.066(4) 0.051(4) -0.007(3) 0.013(4) -0.024(4)
C6 0.061(5) 0.057(4) 0.056(4) 0.003(3) 0.009(3) -0.014(3)
C7 0.058(5) 0.074(5) 0.059(4) 0.003(3) -0.004(3) 0.008(4)
C8 0.052(4) 0.069(4) 0.052(4) -0.011(3) 0.007(3) 0.003(3)
C9 0.054(4) 0.051(4) 0.053(4) 0.003(3) 0.009(3) -0.006(3)
C10 0.059(5) 0.063(4) 0.070(5) 0.003(4) -0.005(4) 0.005(3)
C11 0.062(5) 0.052(4) 0.081(5) -0.005(3) 0.006(4) 0.001(3)
C12 0.067(5) 0.076(5) 0.055(4) 0.008(3) 0.004(3) -0.015(4)
C13 0.082(6) 0.097(6) 0.060(4) 0.002(4) 0.014(4) -0.002(5)
C14 0.054(4) 0.061(4) 0.055(4) 0.002(3) -0.005(3) 0.001(3)
C15 0.094(7) 0.065(5) 0.094(6) 0.012(4) -0.024(5) 0.000(4)
C16 0.074(6) 0.071(5) 0.086(5) -0.008(4) -0.018(4) -0.005(4)
O1 0.074(4) 0.127(5) 0.104(5) -0.038(4) 0.028(3) -0.018(4)
O2 0.123(5) 0.076(4) 0.092(4) 0.011(3) -0.019(4) 0.011(4)
S1 0.0634(12) 0.0595(11) 0.0524(10) 0.0002(8) 0.0036(8) -0.0082(8)
S2 0.0709(13) 0.0563(10) 0.0511(9) -0.0034(8) 0.0062(8) -0.0138(9)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.492(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.521(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.486(11) . ?
C3 S2 1.839(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.511(9) . ?
C5 S2 1.810(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.349(10) . ?
C6 C11 1.395(11) . ?
C7 C8 1.377(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(10) . ?
C9 C12 1.478(9) . ?
C10 C11 1.372(10) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 S1 1.799(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.501(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.511(10) . ?
C14 C16 1.528(10) . ?
C14 S1 1.850(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 S2 1.485(7) . ?
O2 S1 1.481(6) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 114.0(8) . . ?
C4 C3 C2 107.7(7) . . ?
C1 C3 C2 110.8(6) . . ?
C4 C3 S2 108.5(5) . . ?
C1 C3 S2 110.5(5) . . ?
C2 C3 S2 105.0(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S2 110.0(5) . . ?
C6 C5 H5A 109.7 . . ?
S2 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
S2 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C11 118.6(7) . . ?
C7 C6 C5 121.5(7) . . ?
C11 C6 C5 119.9(7) . . ?
C6 C7 C8 121.8(7) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 120.4(6) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 117.4(6) . . ?
C10 C9 C12 121.4(7) . . ?
C8 C9 C12 121.2(6) . . ?
C11 C10 C9 121.6(7) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C6 120.3(7) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C9 C12 S1 112.8(5) . . ?
C9 C12 H12A 109.0 . . ?
S1 C12 H12A 109.0 . . ?
C9 C12 H12B 109.0 . . ?
S1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C13 C14 C15 112.4(7) . . ?
C13 C14 C16 111.5(6) . . ?
C15 C14 C16 110.4(6) . . ?
C13 C14 S1 111.1(5) . . ?
C15 C14 S1 107.9(5) . . ?
C16 C14 S1 103.2(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 S1 C12 106.4(4) . . ?
O2 S1 C14 107.4(3) . . ?
C12 S1 C14 100.6(3) . . ?
O1 S2 C5 105.3(4) . . ?
O1 S2 C3 107.2(3) . . ?
C5 S2 C3 100.1(3) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C5 C6 C7 -85.0(8) . . . . ?
S2 C5 C6 C11 94.9(7) . . . . ?
C11 C6 C7 C8 -0.4(11) . . . . ?
C5 C6 C7 C8 179.5(7) . . . . ?
C6 C7 C8 C9 -0.6(11) . . . . ?
C7 C8 C9 C10 1.2(10) . . . . ?
C7 C8 C9 C12 -177.4(7) . . . . ?
C8 C9 C10 C11 -0.9(10) . . . . ?
C12 C9 C10 C11 177.7(7) . . . . ?
C9 C10 C11 C6 0.0(11) . . . . ?
C7 C6 C11 C10 0.7(11) . . . . ?
C5 C6 C11 C10 -179.2(6) . . . . ?
C10 C9 C12 S1 68.4(8) . . . . ?
C8 C9 C12 S1 -113.0(7) . . . . ?
C9 C12 S1 O2 86.6(6) . . . . ?
C9 C12 S1 C14 -161.5(6) . . . . ?
C13 C14 S1 O2 58.2(6) . . . . ?
C15 C14 S1 O2 -178.3(6) . . . . ?
C16 C14 S1 O2 -61.4(6) . . . . ?
C13 C14 S1 C12 -53.0(6) . . . . ?
C15 C14 S1 C12 70.6(6) . . . . ?
C16 C14 S1 C12 -172.6(5) . . . . ?
C6 C5 S2 O1 82.5(6) . . . . ?
C6 C5 S2 C3 -166.4(6) . . . . ?
C4 C3 S2 O1 174.0(6) . . . . ?
C1 C3 S2 O1 48.5(7) . . . . ?
C2 C3 S2 O1 -71.0(6) . . . . ?
C4 C3 S2 C5 64.4(7) . . . . ?
C1 C3 S2 C5 -61.1(6) . . . . ?
C2 C3 S2 C5 179.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 755516'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,4-bis((tert-butylthio)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 S2'

_chemical_formula_sum            'C16 H26 S2'

_chemical_formula_weight         282.51



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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2

_symmetry_space_group_name_hall  '-P 1'

loop_

_symmetry_equiv_pos_as_xyz


'x, y, z'
'-x, -y, -z'



_cell_length_a                   6.171(5)

_cell_length_b                   12.078(5)

_cell_length_c                   12.267(5)

_cell_angle_alpha                76.243(5)

_cell_angle_beta                 80.572(5)

_cell_angle_gamma                77.970(5)

_cell_volume                     862.3(9)

_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1493

_cell_measurement_theta_min      2.71

_cell_measurement_theta_max      24.68



_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.088

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             308.0

_exptl_absorpt_coefficient_mu    0.293

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          ?

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5111

_diffrn_reflns_av_R_equivalents  0.0127

_diffrn_reflns_av_sigmaI/netI    0.0321

_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -13

_diffrn_reflns_limit_k_max       15

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         1.72

_diffrn_reflns_theta_max         27.59

_reflns_number_total             3686

_reflns_number_gt                2414

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_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.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1107P)²+0.4910P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3686

_refine_ls_number_parameters     169

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1041

_refine_ls_R_factor_gt           0.0732

_refine_ls_wR_factor_ref         0.2324

_refine_ls_wR_factor_gt          0.2064

_refine_ls_goodness_of_fit_ref   1.086

_refine_ls_restrained_S_all      1.086

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



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
C1 C 0.0702(9) 0.0459(4) 0.7739(4) 0.0977(15) Uani 1 1 d . . .
H1A H 0.1846 0.0016 0.7305 0.147 Uiso 1 1 calc R . .
H1B H -0.0505 0.0818 0.7298 0.147 Uiso 1 1 calc R . .
H1C H 0.0162 -0.0044 0.8414 0.147 Uiso 1 1 calc R . .
C2 C -0.0155(8) 0.2084(4) 0.8749(4) 0.0920(14) Uani 1 1 d . . .
H2A H -0.0639 0.1583 0.9439 0.138 Uiso 1 1 calc R . .
H2B H -0.1396 0.2415 0.8324 0.138 Uiso 1 1 calc R . .
H2C H 0.0429 0.2692 0.8920 0.138 Uiso 1 1 calc R . .
C3 C 0.1660(6) 0.1388(3) 0.8053(3) 0.0573(8) Uani 1 1 d . . .
C4 C 0.3639(7) 0.0850(4) 0.8699(4) 0.0869(13) Uani 1 1 d . . .
H4A H 0.3168 0.0345 0.9391 0.130 Uiso 1 1 calc R . .
H4B H 0.4251 0.1449 0.8870 0.130 Uiso 1 1 calc R . .
H4C H 0.4755 0.0412 0.8249 0.130 Uiso 1 1 calc R . .
C5 C 0.3622(7) 0.3418(4) 0.7060(3) 0.0738(11) Uani 1 1 d . . .
H5A H 0.2503 0.3839 0.7538 0.089 Uiso 1 1 calc R . .
H5B H 0.4891 0.3065 0.7474 0.089 Uiso 1 1 calc R . .
C6 C 0.4337(6) 0.4235(3) 0.5990(3) 0.0597(8) Uani 1 1 d . . .
C7 C 0.6567(6) 0.4153(3) 0.5533(3) 0.0652(9) Uani 1 1 d . . .
H7 H 0.7636 0.3578 0.5887 0.078 Uiso 1 1 calc R . .
C8 C 0.7203(6) 0.4909(3) 0.4568(3) 0.0662(9) Uani 1 1 d . . .
H8 H 0.8704 0.4845 0.4281 0.079 Uiso 1 1 calc R . .
C9 C 0.5756(13) 0.3160(9) 0.1996(11) 0.277(8) Uani 1 1 d . . .
H9A H 0.6372 0.3856 0.1712 0.416 Uiso 1 1 calc R . .
H9B H 0.6666 0.2545 0.1671 0.416 Uiso 1 1 calc R . .
H9C H 0.5719 0.2953 0.2804 0.416 Uiso 1 1 calc R . .
C10 C 0.2301(17) 0.4394(5) 0.2007(8) 0.217(5) Uani 1 1 d . . .
H10A H 0.2958 0.4566 0.2592 0.325 Uiso 1 1 calc R . .
H10B H 0.0787 0.4298 0.2277 0.325 Uiso 1 1 calc R . .
H10C H 0.2321 0.5020 0.1357 0.325 Uiso 1 1 calc R . .
C11 C 0.3548(6) 0.3350(3) 0.1703(3) 0.0608(9) Uani 1 1 d . . .
C12 C 0.364(2) 0.3464(8) 0.0474(5) 0.244(7) Uani 1 1 d . . .
H12A H 0.2165 0.3730 0.0256 0.367 Uiso 1 1 calc R . .
H12B H 0.4239 0.2726 0.0282 0.367 Uiso 1 1 calc R . .
H12C H 0.4580 0.4012 0.0083 0.367 Uiso 1 1 calc R . .
C13 C 0.2157(10) 0.1944(4) 0.3815(3) 0.1059(18) Uani 1 1 d . . .
H13A H 0.3678 0.1808 0.3993 0.127 Uiso 1 1 calc R . .
H13B H 0.1358 0.2643 0.4056 0.127 Uiso 1 1 calc R . .
C14 C 0.1041(7) 0.0928(3) 0.4428(3) 0.0662(10) Uani 1 1 d . . .
C15 C 0.2227(7) -0.0187(4) 0.4601(3) 0.0698(10) Uani 1 1 d . . .
H15 H 0.3734 -0.0324 0.4327 0.084 Uiso 1 1 calc R . .
C16 C 0.1192(8) -0.1101(3) 0.5177(3) 0.0721(10) Uani 1 1 d . . .
H16 H 0.2020 -0.1847 0.5300 0.087 Uiso 1 1 calc R . .
S1 S 0.24783(16) 0.23088(8) 0.66878(7) 0.0637(3) Uani 1 1 d . . .
S2 S 0.2159(2) 0.21158(10) 0.23427(8) 0.0863(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.136(4) 0.090(3) 0.081(3) -0.002(2) -0.016(3) -0.068(3)
C2 0.081(3) 0.097(3) 0.083(3) -0.006(2) 0.010(2) -0.012(2)
C3 0.063(2) 0.0584(19) 0.0477(17) -0.0036(14) -0.0055(15) -0.0142(16)
C4 0.084(3) 0.081(3) 0.087(3) 0.010(2) -0.028(2) -0.013(2)
C5 0.092(3) 0.074(2) 0.061(2) -0.0049(18) -0.011(2) -0.036(2)
C6 0.069(2) 0.0545(19) 0.060(2) -0.0083(15) -0.0113(17) -0.0209(16)
C7 0.062(2) 0.054(2) 0.075(2) -0.0060(17) -0.0159(18) -0.0026(16)
C8 0.0514(19) 0.072(2) 0.073(2) -0.0116(18) -0.0044(17) -0.0129(17)
C9 0.119(6) 0.237(10) 0.398(17) 0.178(11) -0.076(8) -0.108(7)
C10 0.283(11) 0.067(4) 0.242(10) -0.023(5) 0.146(9) -0.049(5)
C11 0.072(2) 0.0531(19) 0.0571(19) -0.0063(15) 0.0047(16) -0.0254(17)
C12 0.477(18) 0.246(10) 0.072(4) -0.003(5) 0.016(7) -0.275(12)
C13 0.175(5) 0.107(4) 0.056(2) 0.006(2) -0.016(3) -0.096(4)
C14 0.093(3) 0.067(2) 0.0435(17) -0.0007(15) -0.0089(17) -0.037(2)
C15 0.070(2) 0.086(3) 0.055(2) -0.0142(18) -0.0053(17) -0.019(2)
C16 0.096(3) 0.057(2) 0.061(2) -0.0071(17) -0.020(2) -0.007(2)
S1 0.0802(7) 0.0624(6) 0.0511(5) -0.0052(4) -0.0078(4) -0.0262(5)
S2 0.1283(10) 0.0880(8) 0.0560(6) -0.0024(5) -0.0084(6) -0.0655(7)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.522(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.524(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.511(5) . ?
C3 S1 1.835(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.506(5) . ?
C5 S1 1.815(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.381(5) 2_666 ?
C6 C7 1.391(5) . ?
C7 C8 1.369(5) . ?
C7 H7 0.9300 . ?
C8 C6 1.381(5) 2_666 ?
C8 H8 0.9300 . ?
C9 C11 1.425(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.431(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.474(7) . ?
C11 S2 1.824(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.513(5) . ?
C13 S2 1.768(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C16 1.374(6) 2_556 ?
C14 C15 1.378(6) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9300 . ?
C16 C14 1.374(6) 2_556 ?
C16 H16 0.9300 . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 110.6(4) . . ?
C4 C3 C2 110.9(4) . . ?
C1 C3 C2 109.4(4) . . ?
C4 C3 S1 111.6(3) . . ?
C1 C3 S1 104.1(3) . . ?
C2 C3 S1 110.1(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 108.6(3) . . ?
C6 C5 H5A 110.0 . . ?
S1 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
S1 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C8 C6 C7 117.9(3) 2_666 . ?
C8 C6 C5 121.0(3) 2_666 . ?
C7 C6 C5 121.1(3) . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C6 121.4(3) . 2_666 ?
C7 C8 H8 119.3 . . ?
C6 C8 H8 119.3 2_666 . ?
C11 C9 H9A 109.5 . . ?
C11 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C11 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C10 109.6(8) . . ?
C9 C11 C12 109.4(7) . . ?
C10 C11 C12 109.0(6) . . ?
C9 C11 S2 112.0(4) . . ?
C10 C11 S2 111.6(4) . . ?
C12 C11 S2 105.1(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S2 109.1(3) . . ?
C14 C13 H13A 109.9 . . ?
S2 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
S2 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C16 C14 C15 118.5(3) 2_556 . ?
C16 C14 C13 120.4(4) 2_556 . ?
C15 C14 C13 121.1(4) . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C14 C16 C15 121.1(4) 2_556 . ?
C14 C16 H16 119.4 2_556 . ?
C15 C16 H16 119.4 . . ?
C5 S1 C3 104.19(17) . . ?
C13 S2 C11 104.94(19) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 C8 79.3(4) . . . 2_666 ?
S1 C5 C6 C7 -100.8(4) . . . . ?
C8 C6 C7 C8 0.8(6) 2_666 . . . ?
C5 C6 C7 C8 -179.1(4) . . . . ?
C6 C7 C8 C6 -0.8(6) . . . 2_666 ?
S2 C13 C14 C16 -94.3(4) . . . 2_556 ?
S2 C13 C14 C15 85.5(5) . . . . ?
C16 C14 C15 C16 -1.2(6) 2_556 . . . ?
C13 C14 C15 C16 178.9(4) . . . . ?
C14 C15 C16 C14 1.2(6) . . . 2_556 ?
C6 C5 S1 C3 -179.6(3) . . . . ?
C4 C3 S1 C5 -60.7(3) . . . . ?
C1 C3 S1 C5 -180.0(3) . . . . ?
C2 C3 S1 C5 62.9(3) . . . . ?
C14 C13 S2 C11 -179.7(4) . . . . ?
C9 C11 S2 C13 58.9(8) . . . . ?
C10 C11 S2 C13 -64.4(6) . . . . ?
C12 C11 S2 C13 177.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 766254'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97

_chemical_name_systematic        1,4-bis((tert-butylsulfinyl)methyl)benzene

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 O2 S2'
_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2

_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.927(5)
_cell_length_b                   6.623(5)
_cell_length_c                   11.219(5)
_cell_angle_alpha                80.046(5)
_cell_angle_beta                 89.205(5)
_cell_angle_gamma                84.973(5)
_cell_volume                     432.1(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1248

_cell_measurement_theta_min      3.13

_cell_measurement_theta_max      27.19

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             170.0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2589
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.57
_reflns_number_total             1861
_reflns_number_gt                1598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1017P)²+0.2979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1861
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1758
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1705(5) 0.7256(5) 0.0399(3) 0.0584(7) Uani 1 1 d . . .
H1A H 0.0203 0.6820 0.0513 0.088 Uiso 1 1 calc R . .
H1B H 0.2562 0.6411 -0.0091 0.088 Uiso 1 1 calc R . .
H1C H 0.1624 0.8666 0.0003 0.088 Uiso 1 1 calc R . .
C2 C 0.2868(4) 0.7048(4) 0.1635(2) 0.0419(6) Uani 1 1 d . . .
C3 C 0.1528(6) 0.8321(5) 0.2435(3) 0.0666(9) Uani 1 1 d . . .
H3A H 0.2371 0.8314 0.3161 0.100 Uiso 1 1 calc R . .
H3B H 0.0111 0.7751 0.2641 0.100 Uiso 1 1 calc R . .
H3C H 0.1250 0.9710 0.2014 0.100 Uiso 1 1 calc R . .
C4 C 0.5302(5) 0.7594(6) 0.1472(4) 0.0727(10) Uani 1 1 d . . .
H4A H 0.5338 0.8907 0.0954 0.109 Uiso 1 1 calc R . .
H4B H 0.6171 0.6563 0.1113 0.109 Uiso 1 1 calc R . .
H4C H 0.5937 0.7659 0.2246 0.109 Uiso 1 1 calc R . .
C5 C 0.4410(6) 0.4169(4) 0.3649(3) 0.0631(9) Uani 1 1 d . . .
H5A H 0.5888 0.4666 0.3461 0.076 Uiso 1 1 calc R . .
H5B H 0.3604 0.5061 0.4143 0.076 Uiso 1 1 calc R . .
C6 C 0.4699(5) 0.2000(4) 0.4348(2) 0.0470(6) Uani 1 1 d . . .
C7 C 0.6679(5) 0.0771(5) 0.4238(2) 0.0524(7) Uani 1 1 d . . .
H7 H 0.7819 0.1281 0.3724 0.063 Uiso 1 1 calc R . .
C8 C 0.6974(5) -0.1203(5) 0.4886(3) 0.0534(7) Uani 1 1 d . . .
H8 H 0.8315 -0.2008 0.4807 0.064 Uiso 1 1 calc R . .
O1 O 0.0506(5) 0.3871(4) 0.2581(3) 0.0876(9) Uani 1 1 d . . .
S1 S 0.28554(12) 0.42712(9) 0.22581(6) 0.0469(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0650(18) 0.0529(17) 0.0530(16) 0.0017(13) -0.0095(13) -0.0020(13)
C2 0.0375(12) 0.0366(12) 0.0489(13) 0.0023(10) -0.0026(10) -0.0063(9)
C3 0.076(2) 0.0497(17) 0.075(2) -0.0201(15) -0.0106(16) 0.0098(15)
C4 0.0487(16) 0.072(2) 0.087(2) 0.0226(18) -0.0054(15) -0.0216(15)
C5 0.094(2) 0.0383(14) 0.0550(16) 0.0045(12) -0.0272(15) -0.0144(14)
C6 0.0624(16) 0.0377(13) 0.0395(12) 0.0017(10) -0.0111(11) -0.0107(11)
C7 0.0539(15) 0.0557(16) 0.0441(14) 0.0056(12) 0.0008(11) -0.0132(12)
C8 0.0553(15) 0.0501(16) 0.0512(15) -0.0018(12) -0.0024(12) 0.0019(12)
O1 0.0811(17) 0.0827(18) 0.0953(19) 0.0135(15) -0.0081(14) -0.0416(14)
S1 0.0614(5) 0.0341(4) 0.0445(4) -0.0017(3) -0.0091(3) -0.0092(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.536(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.508(4) . ?
C2 C4 1.519(4) . ?
C2 S1 1.852(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.510(4) . ?
C5 S1 1.811(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.383(4) 2_656 ?
C6 C7 1.385(4) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C6 1.383(4) 2_656 ?
C8 H8 0.9300 . ?
O1 S1 1.469(3) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C4 112.4(3) . . ?
C3 C2 C1 110.6(2) . . ?
C4 C2 C1 110.4(2) . . ?
C3 C2 S1 110.6(2) . . ?
C4 C2 S1 109.11(19) . . ?
C1 C2 S1 103.33(18) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 111.0(2) . . ?
C6 C5 H5A 109.4 . . ?
S1 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
S1 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C8 C6 C7 118.6(2) 2_656 . ?
C8 C6 C5 121.3(3) 2_656 . ?
C7 C6 C5 120.0(3) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C6 120.9(3) . 2_656 ?
C7 C8 H8 119.6 . . ?
C6 C8 H8 119.6 2_656 . ?
O1 S1 C5 107.85(18) . . ?
O1 S1 C2 107.42(14) . . ?
C5 S1 C2 99.69(12) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 C8 -84.2(3) . . . 2_656 ?
S1 C5 C6 C7 96.5(3) . . . . ?
C8 C6 C7 C8 -0.3(5) 2_656 . . . ?
C5 C6 C7 C8 179.1(3) . . . . ?
C6 C7 C8 C6 0.3(5) . . . 2_656 ?
C6 C5 S1 O1 69.2(3) . . . . ?
C6 C5 S1 C2 -178.8(2) . . . . ?
C3 C2 S1 O1 47.1(2) . . . . ?
C4 C2 S1 O1 171.3(2) . . . . ?
C1 C2 S1 O1 -71.3(2) . . . . ?
C3 C2 S1 C5 -65.2(2) . . . . ?
C4 C2 S1 C5 59.0(3) . . . . ?
C1 C2 S1 C5 176.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 766255'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a



_audit_creation_method           SHELXL-97

_chemical_name_systematic        alpha,alpha'-tert-butylsulfinyl-m-xylene

_chemical_name_common            ?

_chemical_formula_moiety         'C16 H26 O2 S2'

_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_melting_point          ?



_exptl_crystal_description       block

_exptl_crystal_colour            white




_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3438(18)
_cell_length_b                   10.203(3)
_cell_length_c                   14.767(4)
_cell_angle_alpha                108.771(4)
_cell_angle_beta                 97.042(4)
_cell_angle_gamma                93.170(4)
_cell_volume                     893.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    977

_cell_measurement_theta_min      2.95

_cell_measurement_theta_max      20.81

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.22

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.169

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             340.0

_exptl_absorpt_coefficient_mu    0.297

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5444
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3920
_reflns_number_gt                2170
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'


_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0730P)²+0.0290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3920
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1667
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4771(7) 0.4100(4) 0.1631(3) 0.1066(15) Uani 1 1 d . . .
H1A H 0.5832 0.4370 0.1296 0.160 Uiso 1 1 calc R . .
H1B H 0.3684 0.4728 0.1698 0.160 Uiso 1 1 calc R . .
H1C H 0.4143 0.3172 0.1268 0.160 Uiso 1 1 calc R . .
C2 C 0.7400(7) 0.3091(4) 0.2521(3) 0.1022(14) Uani 1 1 d . . .
H2A H 0.7901 0.3024 0.3144 0.153 Uiso 1 1 calc R . .
H2B H 0.8583 0.3372 0.2255 0.153 Uiso 1 1 calc R . .
H2C H 0.6733 0.2201 0.2097 0.153 Uiso 1 1 calc R . .
C3 C 0.5809(5) 0.4146(3) 0.2627(2) 0.0591(8) Uani 1 1 d . . .
C4 C 0.4146(8) 0.3929(4) 0.3220(3) 0.132(2) Uani 1 1 d . . .
H4A H 0.3318 0.3050 0.2891 0.197 Uiso 1 1 calc R . .
H4B H 0.3226 0.4663 0.3309 0.197 Uiso 1 1 calc R . .
H4C H 0.4830 0.3936 0.3838 0.197 Uiso 1 1 calc R . .
C5 C 0.8329(6) 0.5862(3) 0.4329(2) 0.0664(9) Uani 1 1 d . . .
H5A H 0.7184 0.5684 0.4666 0.080 Uiso 1 1 calc R . .
H5B H 0.9236 0.5110 0.4250 0.080 Uiso 1 1 calc R . .
C6 C 0.9606(5) 0.7210(3) 0.49174(19) 0.0510(7) Uani 1 1 d . . .
C7 C 1.1628(5) 0.7511(3) 0.4738(2) 0.0608(8) Uani 1 1 d . . .
H7 H 1.2215 0.6867 0.4258 0.073 Uiso 1 1 calc R . .
C8 C 1.2771(5) 0.8759(4) 0.5265(2) 0.0671(9) Uani 1 1 d . . .
H8 H 1.4129 0.8957 0.5136 0.081 Uiso 1 1 calc R . .
C9 C 1.1952(6) 0.9714(3) 0.5972(2) 0.0649(9) Uani 1 1 d . . .
H9 H 1.2760 1.0550 0.6330 0.078 Uiso 1 1 calc R . .
C10 C 0.9915(6) 0.9445(3) 0.61637(19) 0.0587(8) Uani 1 1 d . . .
C11 C 0.8774(5) 0.8179(3) 0.56263(19) 0.0543(8) Uani 1 1 d . . .
H11 H 0.7410 0.7982 0.5749 0.065 Uiso 1 1 calc R . .
C12 C 0.8961(7) 1.0501(3) 0.6926(2) 0.0805(11) Uani 1 1 d . . .
H12A H 0.7418 1.0376 0.6765 0.097 Uiso 1 1 calc R . .
H12B H 0.9451 1.1430 0.6948 0.097 Uiso 1 1 calc R . .
C13 C 0.8548(6) 1.1810(3) 0.8862(2) 0.0718(10) Uani 1 1 d . . .
C14 C 0.6186(7) 1.1731(5) 0.8554(3) 0.1254(18) Uani 1 1 d . . .
H14A H 0.5519 1.0856 0.8540 0.188 Uiso 1 1 calc R . .
H14B H 0.5924 1.1810 0.7920 0.188 Uiso 1 1 calc R . .
H14C H 0.5604 1.2476 0.9003 0.188 Uiso 1 1 calc R . .
C15 C 0.9050(9) 1.1704(5) 0.9872(3) 0.140(2) Uani 1 1 d . . .
H15A H 0.8852 1.2570 1.0346 0.211 Uiso 1 1 calc R . .
H15B H 1.0503 1.1505 0.9979 0.211 Uiso 1 1 calc R . .
H15C H 0.8111 1.0971 0.9926 0.211 Uiso 1 1 calc R . .
C16 C 0.9714(10) 1.3130(4) 0.8825(4) 0.147(2) Uani 1 1 d . . .
H16A H 0.9261 1.3246 0.8213 0.220 Uiso 1 1 calc R . .
H16B H 1.1225 1.3062 0.8901 0.220 Uiso 1 1 calc R . .
H16C H 0.9393 1.3916 0.9337 0.220 Uiso 1 1 calc R . .
O1 O 0.5608(4) 0.6905(2) 0.33300(19) 0.0952(8) Uani 1 1 d . . .
O2 O 0.8507(5) 0.9053(2) 0.80853(19) 0.1051(9) Uani 1 1 d . . .
S1 S 0.72215(13) 0.59022(8) 0.31607(5) 0.0578(3) Uani 1 1 d . . .
S2 S 0.97109(15) 1.03231(8) 0.80919(5) 0.0645(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.118(4) 0.078(3) 0.092(3) 0.010(2) -0.046(3) -0.005(2)
C2 0.128(4) 0.067(2) 0.085(3) -0.004(2) -0.013(2) 0.031(2)
C3 0.068(2) 0.0461(17) 0.0530(17) 0.0048(13) 0.0029(15) 0.0026(15)
C4 0.127(4) 0.089(3) 0.146(4) -0.010(3) 0.065(3) -0.056(3)
C5 0.094(3) 0.0513(18) 0.0488(17) 0.0169(14) -0.0023(16) -0.0087(17)
C6 0.063(2) 0.0457(16) 0.0427(15) 0.0160(13) 0.0003(14) 0.0017(15)
C7 0.070(2) 0.059(2) 0.0510(17) 0.0153(15) 0.0060(16) 0.0119(17)
C8 0.057(2) 0.078(2) 0.069(2) 0.0310(19) 0.0006(17) 0.0008(18)
C9 0.073(2) 0.0524(19) 0.060(2) 0.0181(16) -0.0156(18) -0.0085(17)
C10 0.085(3) 0.0477(17) 0.0393(15) 0.0123(13) -0.0041(16) 0.0127(17)
C11 0.060(2) 0.0600(19) 0.0463(16) 0.0230(15) 0.0047(14) 0.0055(16)
C12 0.123(3) 0.065(2) 0.0468(18) 0.0119(15) -0.0012(19) 0.032(2)
C13 0.093(3) 0.062(2) 0.0504(18) 0.0053(15) 0.0052(18) 0.0187(19)
C14 0.103(4) 0.158(5) 0.101(3) 0.015(3) 0.019(3) 0.057(3)
C15 0.217(6) 0.154(4) 0.050(2) 0.020(3) 0.023(3) 0.101(4)
C16 0.221(6) 0.054(3) 0.140(4) -0.010(3) 0.057(4) -0.001(3)
O1 0.102(2) 0.0527(14) 0.114(2) 0.0162(13) -0.0182(16) 0.0097(14)
O2 0.154(3) 0.0603(16) 0.101(2) 0.0296(14) 0.0180(19) -0.0037(16)
S1 0.0676(6) 0.0531(5) 0.0497(4) 0.0189(4) -0.0013(4) -0.0071(4)
S2 0.0836(7) 0.0558(5) 0.0474(5) 0.0111(4) -0.0025(4) 0.0151(4)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.522(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.501(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.501(5) . ?
C3 S1 1.837(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.496(4) . ?
C5 S1 1.795(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.371(4) . ?
C6 C7 1.379(4) . ?
C7 C8 1.369(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(4) . ?
C10 C12 1.502(4) . ?
C11 H11 0.9300 . ?
C12 S2 1.798(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.502(6) . ?
C13 C16 1.520(5) . ?
C13 C15 1.526(5) . ?
C13 S2 1.832(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 S1 1.473(3) . ?
O2 S2 1.464(3) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 C3 C4 112.2(3) . . ?
C2 C3 C1 109.5(3) . . ?
C4 C3 C1 110.6(4) . . ?
C2 C3 S1 109.3(2) . . ?
C4 C3 S1 110.8(2) . . ?
C1 C3 S1 104.1(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 110.97(19) . . ?
C6 C5 H5A 109.4 . . ?
S1 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
S1 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C11 C6 C7 118.9(3) . . ?
C11 C6 C5 120.8(3) . . ?
C7 C6 C5 120.3(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 C12 120.7(3) . . ?
C9 C10 C12 121.0(3) . . ?
C6 C11 C10 121.6(3) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C12 S2 110.6(2) . . ?
C10 C12 H12A 109.5 . . ?
S2 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
S2 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C16 111.9(4) . . ?
C14 C13 C15 111.5(4) . . ?
C16 C13 C15 110.0(4) . . ?
C14 C13 S2 111.5(3) . . ?
C16 C13 S2 107.9(3) . . ?
C15 C13 S2 103.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 S1 C5 106.29(16) . . ?
O1 S1 C3 107.90(15) . . ?
C5 S1 C3 100.57(14) . . ?
O2 S2 C12 106.80(17) . . ?
O2 S2 C13 107.75(18) . . ?
C12 S2 C13 100.48(15) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 C11 101.4(3) . . . . ?
S1 C5 C6 C7 -77.0(3) . . . . ?
C11 C6 C7 C8 0.2(4) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C8 C9 C10 C12 -178.5(3) . . . . ?
C7 C6 C11 C10 -0.2(4) . . . . ?
C5 C6 C11 C10 -178.6(2) . . . . ?
C9 C10 C11 C6 -0.4(4) . . . . ?
C12 C10 C11 C6 179.0(3) . . . . ?
C11 C10 C12 S2 93.8(3) . . . . ?
C9 C10 C12 S2 -86.8(3) . . . . ?
C6 C5 S1 O1 -68.1(3) . . . . ?
C6 C5 S1 C3 179.5(2) . . . . ?
C2 C3 S1 O1 -175.3(2) . . . . ?
C4 C3 S1 O1 -51.2(3) . . . . ?
C1 C3 S1 O1 67.7(3) . . . . ?
C2 C3 S1 C5 -64.2(3) . . . . ?
C4 C3 S1 C5 59.9(3) . . . . ?
C1 C3 S1 C5 178.9(3) . . . . ?
C10 C12 S2 O2 -72.6(3) . . . . ?
C10 C12 S2 C13 175.1(3) . . . . ?
C14 C13 S2 O2 -53.7(3) . . . . ?
C16 C13 S2 O2 -176.8(3) . . . . ?
C15 C13 S2 O2 66.5(3) . . . . ?
C14 C13 S2 C12 57.9(3) . . . . ?
C16 C13 S2 C12 -65.3(3) . . . . ?
C15 C13 S2 C12 178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.880
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 810941'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

 alpha,alpha'-tert-butylsulfinyl-m-xylene

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C16 H26 O2 S2'

_chemical_formula_sum            
'C16 H26 O2 S2'

_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'


_symmetry_space_group_name_hall  '-P 2ybc'

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                   12.418(5)
_cell_length_b                   6.541(2)
_cell_length_c                   21.609(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.212(6)
_cell_angle_gamma                90.00
_cell_volume                     1752.5(11)
_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    956

_cell_measurement_theta_min      2.43

_cell_measurement_theta_max      18.30



_exptl_crystal_description       block

_exptl_crystal_colour            white

_exptl_crystal_size_max          0.32

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.19

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.192

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             680.0

_exptl_absorpt_coefficient_mu    0.303

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10160
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_sigmaI/netI    0.1199
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4061
_reflns_number_gt                1523
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1322P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2771
_refine_ls_wR_factor_gt          0.2220
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5047(4) 0.6561(10) 0.0783(2) 0.0738(17) Uani 1 1 d . . .
H1A H 0.5412 0.7412 0.0493 0.089 Uiso 1 1 calc R . .
H1B H 0.5475 0.5337 0.0859 0.089 Uiso 1 1 calc R . .
C2 C 0.3955(4) 0.5988(8) 0.0511(2) 0.0575(13) Uani 1 1 d . . .
C3 C 0.3469(4) 0.4203(8) 0.0688(2) 0.0606(14) Uani 1 1 d . . .
H3 H 0.3834 0.3359 0.0976 0.073 Uiso 1 1 calc R . .
C4 C 0.2445(4) 0.3618(8) 0.0449(2) 0.0566(13) Uani 1 1 d . . .
C5 C 0.1937(4) 0.4888(9) 0.0026(2) 0.0622(14) Uani 1 1 d . . .
H5 H 0.1253 0.4546 -0.0139 0.075 Uiso 1 1 calc R . .
C6 C 0.2410(4) 0.6650(9) -0.0160(2) 0.0666(15) Uani 1 1 d . . .
H6 H 0.2046 0.7491 -0.0449 0.080 Uiso 1 1 calc R . .
C7 C 0.3417(4) 0.7190(8) 0.0076(2) 0.0642(14) Uani 1 1 d . . .
H7 H 0.3737 0.8380 -0.0061 0.077 Uiso 1 1 calc R . .
C8 C 0.1961(4) 0.1683(8) 0.0650(3) 0.0718(16) Uani 1 1 d . . .
H8A H 0.2529 0.0715 0.0766 0.086 Uiso 1 1 calc R . .
H8B H 0.1522 0.1101 0.0309 0.086 Uiso 1 1 calc R . .
C9 C 0.1692(4) -0.1858(9) 0.1623(3) 0.0763(16) Uani 1 1 d . . .
H9A H 0.2162 -0.1159 0.1920 0.115 Uiso 1 1 calc R . .
H9B H 0.2069 -0.2122 0.1255 0.115 Uiso 1 1 calc R . .
H9C H 0.1465 -0.3129 0.1795 0.115 Uiso 1 1 calc R . .
C10 C 0.0711(4) -0.0536(7) 0.1460(2) 0.0551(13) Uani 1 1 d . . .
C11 C 0.0053(4) -0.1376(9) 0.0905(3) 0.0732(16) Uani 1 1 d . . .
H11A H -0.0286 -0.2631 0.1017 0.110 Uiso 1 1 calc R . .
H11B H 0.0517 -0.1628 0.0573 0.110 Uiso 1 1 calc R . .
H11C H -0.0490 -0.0401 0.0772 0.110 Uiso 1 1 calc R . .
C12 C 0.6344(4) 0.8113(9) 0.1766(3) 0.0679(15) Uani 1 1 d . . .
C13 C 0.0019(5) -0.0307(9) 0.2013(3) 0.0809(17) Uani 1 1 d . . .
H13A H -0.0295 -0.1604 0.2107 0.121 Uiso 1 1 calc R . .
H13B H -0.0544 0.0668 0.1917 0.121 Uiso 1 1 calc R . .
H13C H 0.0458 0.0160 0.2365 0.121 Uiso 1 1 calc R . .
C14 C 0.6272(6) 0.9224(15) 0.2371(3) 0.140(3) Uani 1 1 d . . .
H14A H 0.5932 0.8359 0.2662 0.210 Uiso 1 1 calc R . .
H14B H 0.5854 1.0448 0.2306 0.210 Uiso 1 1 calc R . .
H14C H 0.6984 0.9575 0.2533 0.210 Uiso 1 1 calc R . .
C15 C 0.6790(7) 0.6053(13) 0.1871(4) 0.143(3) Uani 1 1 d . . .
H15A H 0.7425 0.6135 0.2145 0.214 Uiso 1 1 calc R . .
H15B H 0.6973 0.5473 0.1483 0.214 Uiso 1 1 calc R . .
H15C H 0.6263 0.5206 0.2054 0.214 Uiso 1 1 calc R . .
C16 C 0.6973(5) 0.9232(16) 0.1294(4) 0.139(4) Uani 1 1 d . . .
H16A H 0.6514 1.0220 0.1082 0.209 Uiso 1 1 calc R . .
H16B H 0.7228 0.8273 0.1000 0.209 Uiso 1 1 calc R . .
H16C H 0.7576 0.9917 0.1500 0.209 Uiso 1 1 calc R . .
O1 O 0.4531(4) 0.9930(7) 0.1324(3) 0.128(2) Uani 1 1 d . . .
O2 O 0.0201(4) 0.3254(7) 0.1093(3) 0.1227(17) Uani 1 1 d . . .
S1 S 0.11385(11) 0.2109(2) 0.13012(7) 0.0627(5) Uani 1 1 d . . .
S2 S 0.49268(10) 0.7899(3) 0.14849(6) 0.0685(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.055(3) 0.099(5) 0.068(4) -0.022(3) 0.008(3) 0.000(3)
C2 0.060(3) 0.058(4) 0.055(3) -0.012(3) 0.006(2) 0.001(3)
C3 0.079(4) 0.052(3) 0.051(3) -0.005(3) 0.001(3) 0.018(3)
C4 0.067(3) 0.049(3) 0.053(3) -0.013(3) 0.007(3) -0.008(3)
C5 0.055(3) 0.071(4) 0.059(3) -0.008(3) -0.006(3) -0.007(3)
C6 0.078(4) 0.067(4) 0.053(3) 0.003(3) -0.005(3) 0.007(3)
C7 0.081(4) 0.054(3) 0.059(3) -0.003(3) 0.012(3) -0.005(3)
C8 0.084(4) 0.048(4) 0.084(4) -0.012(3) 0.009(3) -0.011(3)
C9 0.081(4) 0.058(4) 0.088(4) 0.009(3) -0.015(3) 0.003(3)
C10 0.064(3) 0.035(3) 0.065(3) -0.002(2) -0.009(3) -0.002(2)
C11 0.074(4) 0.062(4) 0.082(4) -0.016(3) -0.013(3) -0.011(3)
C12 0.057(3) 0.080(4) 0.066(4) -0.002(3) -0.008(3) 0.002(3)
C13 0.090(4) 0.069(4) 0.084(4) -0.004(3) 0.014(3) -0.015(3)
C14 0.127(6) 0.205(10) 0.084(5) -0.058(6) -0.040(4) -0.006(6)
C15 0.147(7) 0.108(7) 0.165(8) 0.007(6) -0.073(6) 0.045(6)
C16 0.079(4) 0.219(10) 0.118(6) 0.043(6) -0.015(4) -0.051(5)
O1 0.121(4) 0.081(4) 0.172(5) -0.031(3) -0.064(3) 0.039(3)
O2 0.122(4) 0.081(3) 0.165(5) 0.017(3) 0.008(3) 0.019(3)
S1 0.0715(9) 0.0417(8) 0.0752(10) -0.0060(7) 0.0067(7) -0.0032(7)
S2 0.0568(8) 0.0813(11) 0.0667(10) -0.0148(8) -0.0021(6) 0.0055(8)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.495(7) . ?
C1 S2 1.764(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.371(7) . ?
C2 C3 1.378(7) . ?
C3 C4 1.399(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(7) . ?
C4 C8 1.476(7) . ?
C5 C6 1.364(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 S1 1.807(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.518(6) . ?
C10 C13 1.518(7) . ?
C10 S1 1.847(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.469(9) . ?
C12 C14 1.503(8) . ?
C12 C16 1.508(9) . ?
C12 S2 1.835(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 S2 1.452(5) . ?
O2 S1 1.436(5) . ?

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
C2 C1 S2 110.1(3) . . ?
C2 C1 H1A 109.6 . . ?
S2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
S2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C7 C2 C3 118.1(5) . . ?
C7 C2 C1 121.5(5) . . ?
C3 C2 C1 120.4(5) . . ?
C2 C3 C4 122.2(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 117.2(5) . . ?
C5 C4 C8 122.6(5) . . ?
C3 C4 C8 120.1(5) . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.5(5) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C4 C8 S1 110.7(4) . . ?
C4 C8 H8A 109.5 . . ?
S1 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
S1 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C13 110.8(4) . . ?
C11 C10 C9 111.5(4) . . ?
C13 C10 C9 110.9(4) . . ?
C11 C10 S1 109.8(4) . . ?
C13 C10 S1 103.6(3) . . ?
C9 C10 S1 110.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C14 110.4(6) . . ?
C15 C12 C16 110.2(6) . . ?
C14 C12 C16 114.3(6) . . ?
C15 C12 S2 109.1(5) . . ?
C14 C12 S2 102.8(4) . . ?
C16 C12 S2 109.7(4) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 S1 C8 108.7(3) . . ?
O2 S1 C10 108.1(3) . . ?
C8 S1 C10 100.4(2) . . ?
O1 S2 C1 106.9(3) . . ?
O1 S2 C12 108.4(3) . . ?
C1 S2 C12 101.3(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C1 C2 C7 94.6(5) . . . . ?
S2 C1 C2 C3 -86.4(6) . . . . ?
C7 C2 C3 C4 -1.5(7) . . . . ?
C1 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C2 C3 C4 C8 179.6(5) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C8 C4 C5 C6 -178.8(5) . . . . ?
C4 C5 C6 C7 0.0(8) . . . . ?
C5 C6 C7 C2 -1.3(8) . . . . ?
C3 C2 C7 C6 2.0(7) . . . . ?
C1 C2 C7 C6 -179.0(5) . . . . ?
C5 C4 C8 S1 -88.3(6) . . . . ?
C3 C4 C8 S1 92.5(5) . . . . ?
C4 C8 S1 O2 69.1(5) . . . . ?
C4 C8 S1 C10 -177.6(4) . . . . ?
C11 C10 S1 O2 51.5(4) . . . . ?
C13 C10 S1 O2 -66.9(4) . . . . ?
C9 C10 S1 O2 174.5(4) . . . . ?
C11 C10 S1 C8 -62.3(4) . . . . ?
C13 C10 S1 C8 179.4(3) . . . . ?
C9 C10 S1 C8 60.8(4) . . . . ?
C2 C1 S2 O1 -73.6(5) . . . . ?
C2 C1 S2 C12 172.9(4) . . . . ?
C15 C12 S2 O1 -174.3(5) . . . . ?
C14 C12 S2 O1 68.5(6) . . . . ?
C16 C12 S2 O1 -53.5(6) . . . . ?
C15 C12 S2 C1 -61.9(6) . . . . ?
C14 C12 S2 C1 -179.2(5) . . . . ?
C16 C12 S2 C1 58.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.928
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 810942'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_update_record             
;
2011-06-11 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,2-bis((tert-butylsulfinyl)methyl)benzene
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H26 O2 S2'
_chemical_formula_sum            'C16 H26 O2 S2'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            white

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?
_symmetry_space_group_name_hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.940(7)
_cell_length_b                   19.051(10)
_cell_length_c                   9.493(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.504(7)
_cell_angle_gamma                90.00
_cell_volume                     1779.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    392
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      18.65
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5309
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.1381
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2060
_reflns_number_gt                791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2060
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1811
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1751(5) 0.1004(2) 0.4664(5) 0.1091(17) Uani 1 1 d . . .
H1A H 0.2228 0.0571 0.4854 0.164 Uiso 1 1 calc R . .
H1B H 0.2074 0.1351 0.4240 0.164 Uiso 1 1 calc R . .
H1C H 0.0796 0.0931 0.3842 0.164 Uiso 1 1 calc R . .
C2 C 0.1999(3) 0.12575(17) 0.6338(5) 0.0525(10) Uani 1 1 d . . .
C3 C 0.1490(4) 0.07265(18) 0.7031(6) 0.0952(16) Uani 1 1 d . . .
H3A H 0.0514 0.0723 0.6331 0.143 Uiso 1 1 calc R . .
H3B H 0.1809 0.0850 0.8182 0.143 Uiso 1 1 calc R . .
H3C H 0.1823 0.0269 0.7022 0.143 Uiso 1 1 calc R . .
C4 C 0.3481(3) 0.14366(19) 0.7621(6) 0.0865(14) Uani 1 1 d . . .
H4A H 0.4035 0.1047 0.7731 0.130 Uiso 1 1 calc R . .
H4B H 0.3634 0.1534 0.8710 0.130 Uiso 1 1 calc R . .
H4C H 0.3713 0.1842 0.7237 0.130 Uiso 1 1 calc R . .
C5 C 0.1392(3) 0.23463(15) 0.7799(4) 0.0484(9) Uani 1 1 d . . .
H5A H 0.1146 0.1977 0.8279 0.058 Uiso 1 1 calc R . .
H5B H 0.2362 0.2427 0.8570 0.058 Uiso 1 1 calc R . .
C6 C 0.0638(3) 0.30068(15) 0.7630(4) 0.0444(9) Uani 1 1 d . . .
C7 C 0.1249(4) 0.36426(18) 0.7747(5) 0.0630(11) Uani 1 1 d . . .
H7 H 0.2093 0.3647 0.7908 0.076 Uiso 1 1 calc R . .
C8 C 0.0625(4) 0.42663(18) 0.7628(6) 0.0811(14) Uani 1 1 d . . .
H8 H 0.1051 0.4689 0.7723 0.097 Uiso 1 1 calc R . .
O1 O -0.0478(2) 0.18673(14) 0.4685(3) 0.0794(9) Uani 1 1 d . . .
S1 S 0.09862(10) 0.20734(5) 0.57297(12) 0.0585(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.133(4) 0.108(4) 0.075(4) -0.012(3) 0.052(3) 0.045(3)
C2 0.050(2) 0.052(2) 0.052(3) 0.0013(19) 0.027(2) 0.0085(18)
C3 0.105(4) 0.051(2) 0.144(5) 0.002(3) 0.080(4) 0.003(2)
C4 0.049(3) 0.083(3) 0.108(4) -0.012(3) 0.032(3) 0.013(2)
C5 0.042(2) 0.051(2) 0.049(2) -0.0012(17) 0.0238(19) 0.0033(16)
C6 0.042(2) 0.0397(19) 0.046(2) 0.0045(18) 0.022(2) 0.0003(16)
C7 0.052(2) 0.060(3) 0.068(3) -0.003(2) 0.029(2) -0.008(2)
C8 0.083(3) 0.039(2) 0.103(4) -0.002(2) 0.042(3) -0.0135(19)
O1 0.0485(17) 0.101(2) 0.0602(19) -0.0194(15) 0.0136(15) 0.0114(14)
S1 0.0560(7) 0.0613(6) 0.0505(6) 0.0028(5) 0.0255(5) 0.0123(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.521(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.513(4) . ?
C2 C3 1.509(5) . ?
C2 S1 1.850(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.502(4) . ?
C5 S1 1.813(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C6 1.399(6) 2_556 ?
C6 C7 1.385(4) . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C8 1.368(7) 2_556 ?
C8 H8 0.9300 . ?
O1 S1 1.494(2) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 C1 111.1(3) . . ?
C4 C2 C3 112.1(3) . . ?
C1 C2 C3 110.8(3) . . ?
C4 C2 S1 108.8(2) . . ?
C1 C2 S1 103.6(2) . . ?
C3 C2 S1 110.2(2) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S1 110.4(2) . . ?
C6 C5 H5A 109.6 . . ?
S1 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
S1 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C6 C7 119.04(19) 2_556 . ?
C6 C6 C5 123.09(16) 2_556 . ?
C7 C6 C5 117.9(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8 C8 C7 120.1(2) 2_556 . ?
C8 C8 H8 120.0 2_556 . ?
C7 C8 H8 120.0 . . ?
O1 S1 C5 106.79(15) . . ?
O1 S1 C2 107.39(16) . . ?
C5 S1 C2 100.16(15) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C6 C6 91.7(4) . . . 2_556 ?
S1 C5 C6 C7 -88.6(3) . . . . ?
C6 C6 C7 C8 0.7(6) 2_556 . . . ?
C5 C6 C7 C8 -179.0(3) . . . . ?
C6 C7 C8 C8 -0.8(8) . . . 2_556 ?
C6 C5 S1 O1 -66.6(2) . . . . ?
C6 C5 S1 C2 -178.4(2) . . . . ?
C4 C2 S1 O1 -171.3(3) . . . . ?
C1 C2 S1 O1 70.5(3) . . . . ?
C3 C2 S1 O1 -48.0(3) . . . . ?
C4 C2 S1 C5 -60.0(3) . . . . ?
C1 C2 S1 C5 -178.1(3) . . . . ?
C3 C2 S1 C5 63.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.928
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 833342'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
(R,S)-1,2-bis((tert-butylsulfinyl)methyl)benzene

_chemical_name_common            ?

_chemical_formula_moiety         'C16 H26 O2 S2'

_chemical_formula_sum            'C16 H26 O2 S2'

_chemical_melting_point          ?



_exptl_crystal_description       block

_exptl_crystal_colour            white

_chemical_formula_weight         314.51

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'

_symmetry_cell_setting           orthorhombic

_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ?

_symmetry_space_group_name_hall  'P 2ac 2ab '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4267(16)
_cell_length_b                   15.449(2)
_cell_length_c                   11.1546(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1796.8(5)
_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    964

_cell_measurement_theta_min      2.36

_cell_measurement_theta_max      26.59

_exptl_crystal_size_max          0.29

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.22

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.163

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             680.0

_exptl_absorpt_coefficient_mu    0.296

_exptl_absorpt_correction_type   none

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10429
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_sigmaI/netI    0.1865
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         28.25
_reflns_number_total             4144
_reflns_number_gt                1769
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0147P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_number_reflns         4144
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2124
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2743(5) 0.8788(3) 0.7545(5) 0.107(2) Uani 1 1 d . . .
H1A H 0.1974 0.8673 0.7098 0.160 Uiso 1 1 calc R . .
H1B H 0.3195 0.8256 0.7680 0.160 Uiso 1 1 calc R . .
H1C H 0.3278 0.9178 0.7099 0.160 Uiso 1 1 calc R . .
C2 C 0.2397(5) 0.9195(3) 0.8737(5) 0.0539(14) Uani 1 1 d . . .
C3 C 0.1575(4) 0.9996(3) 0.8550(5) 0.084(2) Uani 1 1 d . . .
H3A H 0.2047 1.0415 0.8094 0.126 Uiso 1 1 calc R . .
H3B H 0.1349 1.0238 0.9314 0.126 Uiso 1 1 calc R . .
H3C H 0.0809 0.9840 0.8124 0.126 Uiso 1 1 calc R . .
C4 C 0.1731(5) 0.8555(3) 0.9561(6) 0.105(2) Uani 1 1 d . . .
H4A H 0.0906 0.8411 0.9237 0.157 Uiso 1 1 calc R . .
H4B H 0.1626 0.8810 1.0340 0.157 Uiso 1 1 calc R . .
H4C H 0.2241 0.8040 0.9628 0.157 Uiso 1 1 calc R . .
C5 C 0.5992(5) 0.8756(3) 1.0318(5) 0.0395(12) Uani 1 1 d . . .
C6 C 0.6038(6) 0.8720(3) 1.1569(5) 0.0539(15) Uani 1 1 d . . .
H6 H 0.5289 0.8619 1.1998 0.065 Uiso 1 1 calc R . .
C7 C 0.7163(6) 0.8833(3) 1.2170(5) 0.0667(16) Uani 1 1 d . . .
H7 H 0.7167 0.8813 1.3003 0.080 Uiso 1 1 calc R . .
C8 C 0.8289(6) 0.8973(3) 1.1566(6) 0.0696(19) Uani 1 1 d . . .
H8 H 0.9056 0.9037 1.1982 0.084 Uiso 1 1 calc R . .
C9 C 0.8265(5) 0.9019(3) 1.0332(6) 0.0594(16) Uani 1 1 d . . .
H9 H 0.9024 0.9121 0.9917 0.071 Uiso 1 1 calc R . .
C10 C 0.7132(5) 0.8917(3) 0.9699(5) 0.0457(13) Uani 1 1 d . . .
C11 C 0.7180(4) 0.8969(2) 0.8351(4) 0.0512(14) Uani 1 1 d . . .
H11A H 0.7919 0.9308 0.8106 0.061 Uiso 1 1 calc R . .
H11B H 0.6415 0.9255 0.8055 0.061 Uiso 1 1 calc R . .
C12 C 0.4745(4) 0.8600(3) 0.9689(4) 0.0460(14) Uani 1 1 d . . .
H12A H 0.4233 0.8196 1.0153 0.055 Uiso 1 1 calc R . .
H12B H 0.4909 0.8341 0.8912 0.055 Uiso 1 1 calc R . .
C13 C 0.8467(5) 0.8727(3) 0.5807(5) 0.0782(19) Uani 1 1 d . . .
H13A H 0.8583 0.8752 0.4954 0.117 Uiso 1 1 calc R . .
H13B H 0.9230 0.8502 0.6174 0.117 Uiso 1 1 calc R . .
H13C H 0.8300 0.9298 0.6109 0.117 Uiso 1 1 calc R . .
C14 C 0.6048(5) 0.8520(3) 0.5754(5) 0.0827(18) Uani 1 1 d . . .
H14A H 0.5970 0.9094 0.6075 0.124 Uiso 1 1 calc R . .
H14B H 0.5379 0.8161 0.6074 0.124 Uiso 1 1 calc R . .
H14C H 0.5975 0.8541 0.4896 0.124 Uiso 1 1 calc R . .
C15 C 0.7350(6) 0.8144(3) 0.6096(4) 0.0554(15) Uani 1 1 d . . .
C16 C 0.7525(6) 0.7256(3) 0.5510(4) 0.099(2) Uani 1 1 d . . .
H16A H 0.7570 0.7323 0.4655 0.148 Uiso 1 1 calc R . .
H16B H 0.6812 0.6891 0.5711 0.148 Uiso 1 1 calc R . .
H16C H 0.8304 0.6997 0.5795 0.148 Uiso 1 1 calc R . .
O1 O 0.8577(4) 0.7563(2) 0.8057(3) 0.0861(13) Uani 1 1 d . . .
O2 O 0.4575(3) 1.0116(2) 0.8581(3) 0.0759(12) Uani 1 1 d . . .
S1 S 0.38543(13) 0.96022(8) 0.94902(13) 0.0525(4) Uani 1 1 d . . .
S2 S 0.72879(14) 0.78932(8) 0.77148(11) 0.0569(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.081(5) 0.139(5) 0.100(6) -0.053(4) -0.032(5) 0.021(4)
C2 0.029(4) 0.058(3) 0.074(4) -0.002(3) -0.004(3) 0.009(3)
C3 0.055(5) 0.078(4) 0.119(6) 0.010(3) -0.020(4) 0.013(3)
C4 0.050(4) 0.081(4) 0.183(7) 0.041(5) -0.009(4) -0.012(3)
C5 0.039(3) 0.038(3) 0.041(4) 0.003(2) -0.001(3) -0.002(2)
C6 0.064(5) 0.061(3) 0.037(4) 0.001(3) 0.008(3) 0.000(3)
C7 0.084(5) 0.072(4) 0.043(4) -0.004(3) -0.015(5) 0.000(4)
C8 0.056(5) 0.075(4) 0.078(5) -0.007(4) -0.025(4) 0.007(3)
C9 0.045(4) 0.068(4) 0.065(5) -0.007(3) 0.000(4) -0.004(3)
C10 0.050(4) 0.046(3) 0.041(4) -0.003(3) -0.001(4) 0.007(3)
C11 0.052(4) 0.048(3) 0.054(4) 0.003(2) 0.007(3) 0.000(3)
C12 0.043(3) 0.042(3) 0.053(4) 0.003(3) 0.006(3) 0.001(2)
C13 0.075(5) 0.101(4) 0.058(5) 0.015(3) 0.015(4) -0.001(4)
C14 0.076(5) 0.115(5) 0.058(5) 0.007(4) -0.007(4) 0.011(4)
C15 0.069(5) 0.064(4) 0.033(3) 0.001(3) 0.007(3) 0.008(3)
C16 0.147(7) 0.081(4) 0.068(4) -0.021(3) 0.030(5) 0.021(4)
O1 0.097(3) 0.099(3) 0.063(3) 0.011(2) -0.004(3) 0.053(2)
O2 0.059(3) 0.063(2) 0.105(3) 0.035(2) 0.009(2) -0.0073(19)
S1 0.0452(9) 0.0485(7) 0.0638(10) -0.0025(8) -0.0023(9) 0.0023(7)
S2 0.0745(12) 0.0533(8) 0.0428(9) 0.0030(7) 0.0068(9) 0.0151(8)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.515(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.520(5) . ?
C2 C4 1.518(6) . ?
C2 S1 1.847(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.397(6) . ?
C5 C10 1.396(6) . ?
C5 C12 1.497(6) . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.508(6) . ?
C11 S2 1.810(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 S1 1.819(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.507(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.525(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.531(5) . ?
C15 S2 1.847(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 S2 1.487(3) . ?
O2 S1 1.491(3) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 110.5(4) . . ?
C1 C2 C4 111.8(5) . . ?
C3 C2 C4 110.8(4) . . ?
C1 C2 S1 110.2(4) . . ?
C3 C2 S1 104.4(3) . . ?
C4 C2 S1 108.8(4) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 118.1(5) . . ?
C6 C5 C12 119.4(5) . . ?
C10 C5 C12 122.4(5) . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.1(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 118.9(5) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C8 C9 C10 121.2(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 119.6(5) . . ?
C9 C10 C11 118.3(5) . . ?
C5 C10 C11 122.1(5) . . ?
C10 C11 S2 110.1(3) . . ?
C10 C11 H11A 109.6 . . ?
S2 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
S2 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C5 C12 S1 111.3(3) . . ?
C5 C12 H12A 109.4 . . ?
S1 C12 H12A 109.4 . . ?
C5 C12 H12B 109.4 . . ?
S1 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C15 C13 H13A 109.5 . . ?
C15 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C15 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C14 114.0(4) . . ?
C13 C15 C16 110.6(4) . . ?
C14 C15 C16 109.9(5) . . ?
C13 C15 S2 111.2(4) . . ?
C14 C15 S2 107.1(4) . . ?
C16 C15 S2 103.5(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 S1 C12 106.2(2) . . ?
O2 S1 C2 106.7(2) . . ?
C12 S1 C2 100.7(2) . . ?
O1 S2 C11 105.7(2) . . ?
O1 S2 C15 106.9(2) . . ?
C11 S2 C15 101.1(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C5 C6 C7 -0.6(7) . . . . ?
C12 C5 C6 C7 178.0(4) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
C6 C7 C8 C9 1.4(8) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C8 C9 C10 C5 -0.6(7) . . . . ?
C8 C9 C10 C11 -179.6(4) . . . . ?
C6 C5 C10 C9 1.2(6) . . . . ?
C12 C5 C10 C9 -177.3(4) . . . . ?
C6 C5 C10 C11 -179.9(4) . . . . ?
C12 C5 C10 C11 1.6(6) . . . . ?
C9 C10 C11 S2 96.2(4) . . . . ?
C5 C10 C11 S2 -82.8(5) . . . . ?
C6 C5 C12 S1 89.5(4) . . . . ?
C10 C5 C12 S1 -92.0(5) . . . . ?
C5 C12 S1 O2 70.0(4) . . . . ?
C5 C12 S1 C2 -179.0(4) . . . . ?
C1 C2 S1 O2 48.5(4) . . . . ?
C3 C2 S1 O2 -70.2(4) . . . . ?
C4 C2 S1 O2 171.4(3) . . . . ?
C1 C2 S1 C12 -62.1(4) . . . . ?
C3 C2 S1 C12 179.1(3) . . . . ?
C4 C2 S1 C12 60.7(4) . . . . ?
C10 C11 S2 O1 -68.1(4) . . . . ?
C10 C11 S2 C15 -179.4(4) . . . . ?
C13 C15 S2 O1 -52.4(4) . . . . ?
C14 C15 S2 O1 -177.6(3) . . . . ?
C16 C15 S2 O1 66.3(4) . . . . ?
C13 C15 S2 C11 57.9(4) . . . . ?
C14 C15 S2 C11 -67.3(4) . . . . ?
C16 C15 S2 C11 176.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 833343'
