# Electronic Supplementary Material (ESI) for ChemComm.
# 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.
#
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#  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
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_cd213561

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O S2'
_chemical_formula_weight         266.40

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   P2(1)/c

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

_cell_length_a                   7.2689(9)
_cell_length_b                   11.4438(14)
_cell_length_c                   17.560(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.396(2)
_cell_angle_gamma                90.00
_cell_volume                     1451.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3330
_cell_measurement_theta_min      4.668
_cell_measurement_theta_max      56.310

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.54533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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            8448
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2843
_reflns_number_gt                2415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0656P)²+0.1329P] 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       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2843
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.43222(6) 0.82689(5) 0.35129(3) 0.05473(19) Uani 1 1 d . . .
S2 S 0.07797(6) 0.90913(4) 0.41212(2) 0.05248(19) Uani 1 1 d . . .
O1 O 0.2101(2) 0.66414(12) 0.19286(8) 0.0670(4) Uani 1 1 d . . .
C1 C 0.2854(3) 0.85786(19) 0.16099(11) 0.0606(5) Uani 1 1 d . . .
H1A H 0.3756 0.8227 0.1321 0.091 Uiso 1 1 calc R . .
H1B H 0.3439 0.9168 0.1943 0.091 Uiso 1 1 calc R . .
H1C H 0.1892 0.8928 0.1265 0.091 Uiso 1 1 calc R . .
C2 C 0.2040(2) 0.76655(16) 0.20775(9) 0.0462(4) Uani 1 1 d . . .
C3 C 0.0969(2) 0.80807(14) 0.27200(9) 0.0409(4) Uani 1 1 d . . .
C4 C 0.1893(2) 0.84609(14) 0.33708(9) 0.0425(4) Uani 1 1 d . . .
C5 C -0.1129(2) 0.79619(15) 0.25686(10) 0.0470(4) Uani 1 1 d . . .
H5 H -0.1663 0.8498 0.2919 0.056 Uiso 1 1 calc R . .
C6 C -0.1816(2) 0.83475(14) 0.17616(10) 0.0443(4) Uani 1 1 d . . .
C7 C -0.2080(3) 0.75732(18) 0.11502(11) 0.0590(5) Uani 1 1 d . . .
H7 H -0.1882 0.6778 0.1235 0.071 Uiso 1 1 calc R . .
C8 C -0.2636(3) 0.7973(3) 0.04161(13) 0.0825(7) Uani 1 1 d . . .
H8 H -0.2802 0.7444 0.0012 0.099 Uiso 1 1 calc R . .
C9 C -0.2942(4) 0.9126(3) 0.02792(17) 0.0938(9) Uani 1 1 d . . .
H9 H -0.3300 0.9389 -0.0216 0.113 Uiso 1 1 calc R . .
C10 C -0.2719(4) 0.9901(2) 0.08780(18) 0.0902(8) Uani 1 1 d . . .
H10 H -0.2945 1.0692 0.0788 0.108 Uiso 1 1 calc R . .
C11 C -0.2161(3) 0.95177(17) 0.16135(13) 0.0637(5) Uani 1 1 d . . .
H11 H -0.2017 1.0054 0.2014 0.076 Uiso 1 1 calc R . .
C12 C -0.1725(3) 0.67268(19) 0.27667(14) 0.0692(6) Uani 1 1 d . . .
H12A H -0.3045 0.6658 0.2661 0.104 Uiso 1 1 calc R . .
H12B H -0.1364 0.6577 0.3300 0.104 Uiso 1 1 calc R . .
H12C H -0.1139 0.6170 0.2463 0.104 Uiso 1 1 calc R . .
C13 C 0.5157(3) 0.9689(2) 0.38114(16) 0.0804(7) Uani 1 1 d . . .
H13A H 0.4930 1.0227 0.3392 0.121 Uiso 1 1 calc R . .
H13B H 0.6463 0.9649 0.3970 0.121 Uiso 1 1 calc R . .
H13C H 0.4526 0.9951 0.4232 0.121 Uiso 1 1 calc R . .
C14 C 0.1711(3) 0.8233(2) 0.49351(11) 0.0692(6) Uani 1 1 d . . .
H14A H 0.1310 0.7437 0.4865 0.104 Uiso 1 1 calc R . .
H14B H 0.1279 0.8541 0.5392 0.104 Uiso 1 1 calc R . .
H14C H 0.3038 0.8264 0.4982 0.104 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 0.0401(3) 0.0751(4) 0.0478(3) -0.0045(2) -0.0005(2) 0.0111(2)
S2 0.0540(3) 0.0634(3) 0.0415(3) -0.00725(18) 0.0116(2) 0.0075(2)
O1 0.0814(11) 0.0630(9) 0.0586(9) -0.0081(6) 0.0166(8) 0.0185(7)
C1 0.0568(11) 0.0817(14) 0.0460(11) -0.0044(9) 0.0173(9) -0.0034(10)
C2 0.0398(9) 0.0615(11) 0.0370(8) -0.0038(7) 0.0026(7) 0.0110(8)
C3 0.0391(8) 0.0481(9) 0.0361(8) 0.0008(6) 0.0064(7) 0.0062(7)
C4 0.0404(9) 0.0508(9) 0.0371(8) 0.0014(6) 0.0080(7) 0.0067(7)
C5 0.0382(9) 0.0580(10) 0.0454(9) -0.0047(8) 0.0073(7) 0.0031(7)
C6 0.0318(8) 0.0488(9) 0.0510(10) -0.0035(7) -0.0012(7) 0.0008(6)
C7 0.0520(11) 0.0644(11) 0.0584(11) -0.0133(9) -0.0034(9) 0.0055(9)
C8 0.0649(14) 0.125(2) 0.0537(13) -0.0167(13) -0.0102(10) 0.0106(14)
C9 0.0698(16) 0.139(3) 0.0685(17) 0.0290(17) -0.0096(13) 0.0150(16)
C10 0.0755(16) 0.0786(16) 0.112(2) 0.0391(16) -0.0088(15) 0.0090(12)
C11 0.0549(11) 0.0508(11) 0.0831(15) -0.0011(9) -0.0030(10) 0.0001(9)
C12 0.0560(12) 0.0758(14) 0.0769(15) 0.0193(11) 0.0116(11) -0.0052(10)
C13 0.0519(12) 0.0896(17) 0.0991(18) -0.0054(13) 0.0058(12) -0.0156(11)
C14 0.0804(15) 0.0908(15) 0.0371(10) 0.0036(9) 0.0097(10) -0.0011(11)

_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 C4 1.7691(17) . ?
S1 C13 1.792(2) . ?
S2 C4 1.7747(16) . ?
S2 C14 1.803(2) . ?
O1 C2 1.203(2) . ?
C1 C2 1.492(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.517(2) . ?
C3 C4 1.333(2) . ?
C3 C5 1.524(2) . ?
C5 C6 1.515(2) . ?
C5 C12 1.530(3) . ?
C5 H5 0.9800 . ?
C6 C11 1.382(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.355(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C4 S1 C13 103.23(10) . . ?
C4 S2 C14 101.84(9) . . ?
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 . . ?
O1 C2 C1 122.46(16) . . ?
O1 C2 C3 120.07(16) . . ?
C1 C2 C3 117.27(15) . . ?
C4 C3 C2 119.23(15) . . ?
C4 C3 C5 125.30(14) . . ?
C2 C3 C5 115.39(14) . . ?
C3 C4 S1 118.72(12) . . ?
C3 C4 S2 122.76(13) . . ?
S1 C4 S2 118.45(9) . . ?
C6 C5 C3 110.87(13) . . ?
C6 C5 C12 114.20(16) . . ?
C3 C5 C12 110.22(15) . . ?
C6 C5 H5 107.1 . . ?
C3 C5 H5 107.1 . . ?
C12 C5 H5 107.1 . . ?
C11 C6 C7 117.79(18) . . ?
C11 C6 C5 119.50(16) . . ?
C7 C6 C5 122.69(16) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C2 C3 C4 107.9(2) . . . . ?
C1 C2 C3 C4 -77.1(2) . . . . ?
O1 C2 C3 C5 -69.0(2) . . . . ?
C1 C2 C3 C5 105.94(18) . . . . ?
C2 C3 C4 S1 -9.1(2) . . . . ?
C5 C3 C4 S1 167.59(13) . . . . ?
C2 C3 C4 S2 173.94(12) . . . . ?
C5 C3 C4 S2 -9.4(2) . . . . ?
C13 S1 C4 C3 130.89(16) . . . . ?
C13 S1 C4 S2 -52.00(14) . . . . ?
C14 S2 C4 C3 127.40(16) . . . . ?
C14 S2 C4 S1 -49.59(13) . . . . ?
C4 C3 C5 C6 139.91(17) . . . . ?
C2 C3 C5 C6 -43.30(19) . . . . ?
C4 C3 C5 C12 -92.7(2) . . . . ?
C2 C3 C5 C12 84.13(19) . . . . ?
C3 C5 C6 C11 -85.0(2) . . . . ?
C12 C5 C6 C11 149.82(17) . . . . ?
C3 C5 C6 C7 93.58(19) . . . . ?
C12 C5 C6 C7 -31.6(2) . . . . ?
C11 C6 C7 C8 1.3(3) . . . . ?
C5 C6 C7 C8 -177.27(18) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C6 0.1(4) . . . . ?
C7 C6 C11 C10 -1.2(3) . . . . ?
C5 C6 C11 C10 177.45(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 988290'
