# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
# 
#  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_k293

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33

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   P21/n

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

_cell_length_a                   13.1132(16)
_cell_length_b                   7.6905(9)
_cell_length_c                   28.214(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.057(2)
_cell_angle_gamma                90.00
_cell_volume                     2771.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5966
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.80

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8975
_exptl_absorpt_correction_T_max  0.9314
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 SADABS;sheldrick 1996
;

_diffrn_ambient_temperature      93(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15993
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         27.10
_reflns_number_total             6023
_reflns_number_gt                5138
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0852P)²+2.0085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6023
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1842
_refine_ls_wR_factor_gt          0.1785
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
S12 S 0.50676(5) 0.17127(9) 0.13547(3) 0.0519(2) Uani 1 1 d . . .
S30 S 1.13212(6) 0.68109(9) 0.13793(3) 0.0546(2) Uani 1 1 d . . .
C18 C 0.42292(19) 0.4988(4) 0.11262(10) 0.0450(6) Uani 1 1 d . . .
O1 O 0.57200(16) 0.3066(3) 0.04898(7) 0.0607(6) Uani 1 1 d . . .
O19 O 0.98177(18) 0.8160(3) 0.05223(8) 0.0621(6) Uani 1 1 d . . .
C1 C 0.6483(2) 0.2583(3) 0.07949(9) 0.0420(6) Uani 1 1 d . . .
C13 C 0.48202(18) 0.3922(3) 0.14824(9) 0.0409(5) Uani 1 1 d . . .
C10 C 0.8401(2) 0.2061(3) 0.10397(10) 0.0434(6) Uani 1 1 d . . .
C19 C 0.9359(2) 0.7638(3) 0.08220(10) 0.0449(6) Uani 1 1 d . . .
C9 C 0.7544(2) 0.2723(3) 0.07027(9) 0.0414(5) Uani 1 1 d . . .
O22 O 0.78400(19) 0.5432(4) 0.17939(8) 0.0739(7) Uani 1 1 d . . .
C2 C 0.6364(2) 0.1834(3) 0.12641(9) 0.0415(5) Uani 1 1 d . . .
C21 C 0.9450(2) 0.6133(4) 0.16099(10) 0.0458(6) Uani 1 1 d . . .
C27 C 0.8197(2) 0.7722(3) 0.07266(9) 0.0442(6) Uani 1 1 d . . .
C3 C 0.7180(2) 0.1124(4) 0.15838(9) 0.0452(6) Uani 1 1 d . . .
C31 C 1.16453(19) 0.9046(4) 0.14973(10) 0.0437(6) Uani 1 1 d . . .
C28 C 0.7684(2) 0.7012(3) 0.10654(10) 0.0460(6) Uani 1 1 d . . .
O4 O 0.89714(16) 0.0485(4) 0.17640(8) 0.0680(6) Uani 1 1 d . . .
C32 C 1.1934(2) 1.0068(4) 0.11449(10) 0.0461(6) Uani 1 1 d . . .
O32 O 1.18710(19) 0.9503(3) 0.06825(8) 0.0673(6) Uani 1 1 d . . .
H32 H 1.1354 0.8837 0.0599 0.101 Uiso 1 1 calc R . .
O18 O 0.38905(18) 0.4478(3) 0.06605(8) 0.0674(6) Uani 1 1 d . . .
H18 H 0.4288 0.3698 0.0597 0.101 Uiso 1 1 calc R . .
C22 C 0.8281(2) 0.6149(4) 0.15091(10) 0.0491(6) Uani 1 1 d . . .
C4 C 0.8248(2) 0.1179(4) 0.14814(9) 0.0463(6) Uani 1 1 d . . .
C17 C 0.3951(2) 0.6641(4) 0.12515(12) 0.0545(7) Uani 1 1 d . . .
H17 H 0.3534 0.7368 0.1011 0.065 Uiso 1 1 calc R . .
C20 C 0.9937(2) 0.6876(3) 0.12899(10) 0.0428(6) Uani 1 1 d . . .
C23 C 0.6595(2) 0.7083(4) 0.09753(12) 0.0575(8) Uani 1 1 d . . .
H23 H 0.6239 0.6617 0.1205 0.069 Uiso 1 1 calc R . .
C8 C 0.7690(3) 0.3512(4) 0.02785(11) 0.0529(7) Uani 1 1 d . . .
H8 H 0.7112 0.3983 0.0050 0.063 Uiso 1 1 calc R . .
C33 C 1.2310(2) 1.1729(4) 0.12657(13) 0.0567(8) Uani 1 1 d . . .
H33 H 1.2524 1.2431 0.1028 0.068 Uiso 1 1 calc R . .
C34 C 1.2377(2) 1.2369(4) 0.17251(14) 0.0643(9) Uani 1 1 d . . .
H34 H 1.2647 1.3505 0.1805 0.077 Uiso 1 1 calc R . .
C14 C 0.5141(2) 0.4539(4) 0.19554(10) 0.0522(7) Uani 1 1 d . . .
H14 H 0.5550 0.3819 0.2200 0.063 Uiso 1 1 calc R . .
C25 C 0.6550(3) 0.8531(5) 0.02207(13) 0.0664(9) Uani 1 1 d . . .
H25 H 0.6156 0.9051 -0.0069 0.080 Uiso 1 1 calc R . .
C26 C 0.7635(3) 0.8487(4) 0.03054(11) 0.0557(7) Uani 1 1 d . . .
H26 H 0.7985 0.8975 0.0077 0.067 Uiso 1 1 calc R . .
C5 C 0.9399(2) 0.2167(4) 0.09480(12) 0.0557(7) Uani 1 1 d . . .
H5 H 0.9985 0.1715 0.1177 0.067 Uiso 1 1 calc R . .
C29 C 0.9997(3) 0.5270(5) 0.20728(12) 0.0668(9) Uani 1 1 d . . .
H29A H 0.9874 0.4013 0.2047 0.100 Uiso 1 1 calc R . .
H29B H 0.9726 0.5732 0.2344 0.100 Uiso 1 1 calc R . .
H29C H 1.0751 0.5499 0.2131 0.100 Uiso 1 1 calc R . .
C24 C 0.6037(3) 0.7828(5) 0.05529(13) 0.0670(9) Uani 1 1 d . . .
H24 H 0.5295 0.7859 0.0489 0.080 Uiso 1 1 calc R . .
C7 C 0.8693(3) 0.3603(4) 0.01940(13) 0.0645(9) Uani 1 1 d . . .
H7 H 0.8799 0.4136 -0.0095 0.077 Uiso 1 1 calc R . .
C16 C 0.4276(3) 0.7225(4) 0.17197(13) 0.0619(8) Uani 1 1 d . . .
H16 H 0.4089 0.8361 0.1801 0.074 Uiso 1 1 calc R . .
C35 C 1.2058(3) 1.1391(5) 0.20703(13) 0.0656(9) Uani 1 1 d . . .
H35 H 1.2087 1.1855 0.2385 0.079 Uiso 1 1 calc R . .
C6 C 0.9536(3) 0.2927(5) 0.05255(13) 0.0651(9) Uani 1 1 d . . .
H6 H 1.0216 0.2986 0.0462 0.078 Uiso 1 1 calc R . .
C11 C 0.7104(3) 0.0273(6) 0.20485(12) 0.0741(10) Uani 1 1 d . . .
H11A H 0.6407 0.0475 0.2109 0.111 Uiso 1 1 calc R . .
H11B H 0.7635 0.0763 0.2316 0.111 Uiso 1 1 calc R . .
H11C H 0.7221 -0.0980 0.2026 0.111 Uiso 1 1 calc R . .
C36 C 1.1694(2) 0.9713(4) 0.19566(11) 0.0537(7) Uani 1 1 d . . .
H36 H 1.1478 0.9021 0.2195 0.064 Uiso 1 1 calc R . .
C15 C 0.4868(3) 0.6191(5) 0.20726(12) 0.0649(8) Uani 1 1 d . . .
H15 H 0.5089 0.6609 0.2396 0.078 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
S12 C2 1.777(3) . ?
S12 C13 1.782(3) . ?
S30 C20 1.775(3) . ?
S30 C31 1.784(3) . ?
C18 O18 1.347(3) . ?
C18 C13 1.389(4) . ?
C18 C17 1.390(4) . ?
O1 C1 1.221(3) . ?
O19 C19 1.211(3) . ?
C1 C9 1.476(4) . ?
C1 C2 1.484(4) . ?
C13 C14 1.389(4) . ?
C10 C5 1.394(4) . ?
C10 C9 1.394(4) . ?
C10 C4 1.472(4) . ?
C19 C20 1.486(4) . ?
C19 C27 1.488(4) . ?
C9 C8 1.393(4) . ?
O22 C22 1.222(3) . ?
C2 C3 1.349(4) . ?
C21 C20 1.346(4) . ?
C21 C22 1.495(4) . ?
C21 C29 1.496(4) . ?
C27 C26 1.381(4) . ?
C27 C28 1.398(4) . ?
C3 C11 1.488(4) . ?
C3 C4 1.493(4) . ?
C31 C36 1.381(4) . ?
C31 C32 1.386(4) . ?
C28 C23 1.394(4) . ?
C28 C22 1.476(4) . ?
O4 C4 1.216(3) . ?
C32 O32 1.360(4) . ?
C32 C33 1.384(4) . ?
O32 H32 0.8400 . ?
O18 H18 0.8400 . ?
C17 C16 1.369(5) . ?
C17 H17 0.9500 . ?
C23 C24 1.375(5) . ?
C23 H23 0.9500 . ?
C8 C7 1.390(5) . ?
C8 H8 0.9500 . ?
C33 C34 1.371(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.369(5) . ?
C34 H34 0.9500 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C25 C24 1.381(5) . ?
C25 C26 1.389(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C24 H24 0.9500 . ?
C7 C6 1.378(5) . ?
C7 H7 0.9500 . ?
C16 C15 1.370(5) . ?
C16 H16 0.9500 . ?
C35 C36 1.388(5) . ?
C35 H35 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C36 H36 0.9500 . ?
C15 H15 0.9500 . ?

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 S12 C13 101.69(12) . . ?
C20 S30 C31 101.08(12) . . ?
O18 C18 C13 122.8(3) . . ?
O18 C18 C17 117.8(3) . . ?
C13 C18 C17 119.4(3) . . ?
O1 C1 C9 120.6(2) . . ?
O1 C1 C2 120.8(2) . . ?
C9 C1 C2 118.6(2) . . ?
C14 C13 C18 119.5(3) . . ?
C14 C13 S12 119.4(2) . . ?
C18 C13 S12 120.9(2) . . ?
C5 C10 C9 119.9(3) . . ?
C5 C10 C4 119.8(3) . . ?
C9 C10 C4 120.2(2) . . ?
O19 C19 C20 121.1(3) . . ?
O19 C19 C27 120.6(3) . . ?
C20 C19 C27 118.3(2) . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 C1 120.1(2) . . ?
C10 C9 C1 120.0(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 S12 121.5(2) . . ?
C1 C2 S12 116.45(18) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 C29 124.6(3) . . ?
C22 C21 C29 116.0(2) . . ?
C26 C27 C28 120.6(3) . . ?
C26 C27 C19 120.0(3) . . ?
C28 C27 C19 119.4(2) . . ?
C2 C3 C11 124.5(3) . . ?
C2 C3 C4 119.7(2) . . ?
C11 C3 C4 115.8(2) . . ?
C36 C31 C32 120.0(3) . . ?
C36 C31 S30 119.4(2) . . ?
C32 C31 S30 120.3(2) . . ?
C23 C28 C27 119.5(3) . . ?
C23 C28 C22 119.8(3) . . ?
C27 C28 C22 120.7(3) . . ?
O32 C32 C33 118.2(3) . . ?
O32 C32 C31 122.7(3) . . ?
C33 C32 C31 119.1(3) . . ?
C32 O32 H32 109.5 . . ?
C18 O18 H18 109.5 . . ?
O22 C22 C28 121.4(3) . . ?
O22 C22 C21 119.2(3) . . ?
C28 C22 C21 119.3(2) . . ?
O4 C4 C10 121.5(3) . . ?
O4 C4 C3 119.2(3) . . ?
C10 C4 C3 119.3(2) . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C21 C20 C19 122.6(3) . . ?
C21 C20 S30 121.2(2) . . ?
C19 C20 S30 115.93(19) . . ?
C24 C23 C28 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C28 C23 H23 120.1 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 120.7(3) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C24 C25 C26 120.7(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 119.1(3) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C6 C5 C10 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C10 C5 H5 120.1 . . ?
C21 C29 H29A 109.5 . . ?
C21 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C21 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C34 C35 C36 119.4(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C31 C36 C35 120.2(3) . . ?
C31 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?

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
O18 C18 C13 C14 -179.9(3) . . . . ?
C17 C18 C13 C14 -1.3(4) . . . . ?
O18 C18 C13 S12 -5.9(4) . . . . ?
C17 C18 C13 S12 172.7(2) . . . . ?
C2 S12 C13 C14 -85.3(2) . . . . ?
C2 S12 C13 C18 100.7(2) . . . . ?
C5 C10 C9 C8 -1.0(4) . . . . ?
C4 C10 C9 C8 -178.2(2) . . . . ?
C5 C10 C9 C1 178.9(2) . . . . ?
C4 C10 C9 C1 1.7(4) . . . . ?
O1 C1 C9 C8 4.2(4) . . . . ?
C2 C1 C9 C8 -176.2(2) . . . . ?
O1 C1 C9 C10 -175.7(3) . . . . ?
C2 C1 C9 C10 3.9(3) . . . . ?
O1 C1 C2 C3 172.8(3) . . . . ?
C9 C1 C2 C3 -6.8(4) . . . . ?
O1 C1 C2 S12 -0.8(3) . . . . ?
C9 C1 C2 S12 179.65(18) . . . . ?
C13 S12 C2 C3 110.9(2) . . . . ?
C13 S12 C2 C1 -75.5(2) . . . . ?
O19 C19 C27 C26 -3.6(4) . . . . ?
C20 C19 C27 C26 177.3(2) . . . . ?
O19 C19 C27 C28 176.0(3) . . . . ?
C20 C19 C27 C28 -3.0(4) . . . . ?
C1 C2 C3 C11 -176.8(3) . . . . ?
S12 C2 C3 C11 -3.6(4) . . . . ?
C1 C2 C3 C4 3.8(4) . . . . ?
S12 C2 C3 C4 177.01(19) . . . . ?
C20 S30 C31 C36 80.4(2) . . . . ?
C20 S30 C31 C32 -105.1(2) . . . . ?
C26 C27 C28 C23 0.0(4) . . . . ?
C19 C27 C28 C23 -179.7(2) . . . . ?
C26 C27 C28 C22 178.2(3) . . . . ?
C19 C27 C28 C22 -1.4(4) . . . . ?
C36 C31 C32 O32 -177.8(3) . . . . ?
S30 C31 C32 O32 7.8(4) . . . . ?
C36 C31 C32 C33 2.6(4) . . . . ?
S30 C31 C32 C33 -171.8(2) . . . . ?
C23 C28 C22 O22 2.7(4) . . . . ?
C27 C28 C22 O22 -175.5(3) . . . . ?
C23 C28 C22 C21 -178.0(3) . . . . ?
C27 C28 C22 C21 3.7(4) . . . . ?
C20 C21 C22 O22 178.0(3) . . . . ?
C29 C21 C22 O22 -2.1(4) . . . . ?
C20 C21 C22 C28 -1.3(4) . . . . ?
C29 C21 C22 C28 178.6(3) . . . . ?
C5 C10 C4 O4 -2.3(4) . . . . ?
C9 C10 C4 O4 174.8(3) . . . . ?
C5 C10 C4 C3 178.1(2) . . . . ?
C9 C10 C4 C3 -4.8(4) . . . . ?
C2 C3 C4 O4 -177.6(3) . . . . ?
C11 C3 C4 O4 2.9(4) . . . . ?
C2 C3 C4 C10 2.0(4) . . . . ?
C11 C3 C4 C10 -177.5(3) . . . . ?
O18 C18 C17 C16 -179.9(3) . . . . ?
C13 C18 C17 C16 1.4(4) . . . . ?
C22 C21 C20 C19 -3.4(4) . . . . ?
C29 C21 C20 C19 176.8(3) . . . . ?
C22 C21 C20 S30 -177.28(19) . . . . ?
C29 C21 C20 S30 2.9(4) . . . . ?
O19 C19 C20 C21 -173.4(3) . . . . ?
C27 C19 C20 C21 5.6(4) . . . . ?
O19 C19 C20 S30 0.7(3) . . . . ?
C27 C19 C20 S30 179.82(18) . . . . ?
C31 S30 C20 C21 -111.9(2) . . . . ?
C31 S30 C20 C19 73.8(2) . . . . ?
C27 C28 C23 C24 0.8(4) . . . . ?
C22 C28 C23 C24 -177.5(3) . . . . ?
C10 C9 C8 C7 1.1(4) . . . . ?
C1 C9 C8 C7 -178.8(3) . . . . ?
O32 C32 C33 C34 179.2(3) . . . . ?
C31 C32 C33 C34 -1.3(4) . . . . ?
C32 C33 C34 C35 -1.0(5) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
S12 C13 C14 C15 -173.6(2) . . . . ?
C28 C27 C26 C25 -0.4(4) . . . . ?
C19 C27 C26 C25 179.2(3) . . . . ?
C24 C25 C26 C27 0.2(5) . . . . ?
C9 C10 C5 C6 0.1(4) . . . . ?
C4 C10 C5 C6 177.3(3) . . . . ?
C28 C23 C24 C25 -1.0(5) . . . . ?
C26 C25 C24 C23 0.5(5) . . . . ?
C9 C8 C7 C6 -0.2(5) . . . . ?
C18 C17 C16 C15 -0.7(5) . . . . ?
C33 C34 C35 C36 1.9(5) . . . . ?
C10 C5 C6 C7 0.7(5) . . . . ?
C8 C7 C6 C5 -0.7(5) . . . . ?
C32 C31 C36 C35 -1.7(4) . . . . ?
S30 C31 C36 C35 172.7(2) . . . . ?
C34 C35 C36 C31 -0.6(5) . . . . ?
C17 C16 C15 C14 0.0(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O18 H18 O1 0.84 2.03 2.773(3) 147.5 .
O32 H32 O19 0.84 2.04 2.823(3) 154.0 .

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 1000471'
#######################################################################
#
#                 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_im1741a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33
_chemical_absolute_configuration unk

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   P21

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

_cell_length_a                   10.900(3)
_cell_length_b                   5.5397(12)
_cell_length_c                   11.358(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.555(4)
_cell_angle_gamma                90.00
_cell_volume                     674.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2672
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      27.55

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5013
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         27.55
_reflns_number_total             2773
_reflns_number_gt                2672
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0318P)²+0.5197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   1.12(9)
_refine_ls_number_reflns         2773
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.2243(2) 0.3150(4) 0.2141(2) 0.0175(5) Uani 1 1 d . . .
C2 C 0.1345(2) 0.4707(4) 0.2640(2) 0.0189(5) Uani 1 1 d . . .
C3 C 0.0777(2) 0.6616(5) 0.2017(2) 0.0195(5) Uani 1 1 d . . .
C4 C 0.1149(2) 0.7392(5) 0.0871(2) 0.0184(5) Uani 1 1 d . . .
C5 C 0.2480(2) 0.6669(5) -0.0657(2) 0.0220(5) Uani 1 1 d . . .
H5 H 0.2140 0.8087 -0.1060 0.026 Uiso 1 1 calc R . .
C6 C 0.3353(2) 0.5313(5) -0.1118(2) 0.0231(6) Uani 1 1 d . . .
H6 H 0.3605 0.5797 -0.1840 0.028 Uiso 1 1 calc R . .
C7 C 0.3857(2) 0.3244(5) -0.0524(2) 0.0220(5) Uani 1 1 d . . .
H7 H 0.4451 0.2313 -0.0844 0.026 Uiso 1 1 calc R . .
C8 C 0.3496(2) 0.2534(5) 0.0537(2) 0.0197(5) Uani 1 1 d . . .
H8 H 0.3849 0.1131 0.0946 0.024 Uiso 1 1 calc R . .
C9 C 0.2616(2) 0.3882(5) 0.10016(19) 0.0169(4) Uani 1 1 d . . .
C10 C 0.2104(2) 0.5952(4) 0.0399(2) 0.0180(5) Uani 1 1 d . . .
C11 C -0.0224(2) 0.8097(5) 0.2412(2) 0.0276(6) Uani 1 1 d . . .
H11A H -0.1044 0.7435 0.2062 0.041 Uiso 1 1 calc R . .
H11B H -0.0166 0.9769 0.2145 0.041 Uiso 1 1 calc R . .
H11C H -0.0117 0.8056 0.3287 0.041 Uiso 1 1 calc R . .
O1 O 0.26384(16) 0.1276(3) 0.26584(15) 0.0216(4) Uani 1 1 d . . .
O4 O 0.07067(17) 0.9202(3) 0.03567(16) 0.0249(4) Uani 1 1 d . . .
C13 C 0.2375(2) 0.3449(5) 0.49584(19) 0.0193(5) Uani 1 1 d . . .
C14 C 0.3292(2) 0.5203(5) 0.5051(2) 0.0193(5) Uani 1 1 d . . .
H14 H 0.3148 0.6614 0.4570 0.023 Uiso 1 1 calc R . .
C15 C 0.4420(2) 0.4927(5) 0.5840(2) 0.0196(5) Uani 1 1 d . . .
H15 H 0.5052 0.6123 0.5886 0.024 Uiso 1 1 calc R . .
C16 C 0.4615(2) 0.2884(4) 0.6561(2) 0.0179(5) Uani 1 1 d . . .
C17 C 0.3697(2) 0.1129(5) 0.6484(2) 0.0205(5) Uani 1 1 d . . .
H17 H 0.3834 -0.0256 0.6985 0.025 Uiso 1 1 calc R . .
C18 C 0.2583(2) 0.1378(5) 0.5683(2) 0.0198(5) Uani 1 1 d . . .
H18 H 0.1962 0.0158 0.5624 0.024 Uiso 1 1 calc R . .
O16 O 0.57000(16) 0.2536(3) 0.73723(15) 0.0228(4) Uani 1 1 d . . .
H16 H 0.6190 0.3691 0.7331 0.034 Uiso 1 1 calc R . .
S12 S 0.09078(5) 0.38088(13) 0.39968(5) 0.02372(15) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.231(3) . ?
C1 C9 1.482(3) . ?
C1 C2 1.492(3) . ?
C2 C3 1.358(3) . ?
C2 S12 1.766(2) . ?
C3 C4 1.495(3) . ?
C3 C11 1.498(3) . ?
C4 O4 1.215(3) . ?
C4 C10 1.487(3) . ?
C5 C6 1.388(4) . ?
C5 C10 1.394(3) . ?
C6 C7 1.391(4) . ?
C7 C8 1.392(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.398(4) . ?
C13 C14 1.384(3) . ?
C13 C18 1.406(3) . ?
C13 S12 1.775(2) . ?
C14 C15 1.392(3) . ?
C15 C16 1.390(3) . ?
C16 O16 1.374(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.385(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
O1 C1 C9 121.3(2) . . ?
O1 C1 C2 120.1(2) . . ?
C9 C1 C2 118.5(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 S12 120.30(19) . . ?
C1 C2 S12 118.01(18) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 C11 123.9(2) . . ?
C4 C3 C11 115.6(2) . . ?
O4 C4 C10 120.8(2) . . ?
O4 C4 C3 120.6(2) . . ?
C10 C4 C3 118.6(2) . . ?
C6 C5 C10 120.0(2) . . ?
C5 C6 C7 120.0(2) . . ?
C6 C7 C8 120.2(2) . . ?
C7 C8 C9 120.0(2) . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 C1 120.1(2) . . ?
C10 C9 C1 120.2(2) . . ?
C5 C10 C9 120.1(2) . . ?
C5 C10 C4 119.5(2) . . ?
C9 C10 C4 120.4(2) . . ?
C14 C13 C18 119.5(2) . . ?
C14 C13 S12 121.61(19) . . ?
C18 C13 S12 118.82(19) . . ?
C13 C14 C15 120.8(2) . . ?
C16 C15 C14 119.4(2) . . ?
O16 C16 C17 117.8(2) . . ?
O16 C16 C15 122.0(2) . . ?
C17 C16 C15 120.3(2) . . ?
C18 C17 C16 120.5(2) . . ?
C17 C18 C13 119.6(2) . . ?
C2 S12 C13 102.22(11) . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1000472'
