# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1474252'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 O2 S'
_chemical_formula_weight         372.46

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)/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                   9.2961(2)
_cell_length_b                   10.1519(2)
_cell_length_c                   20.8230(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2670(10)
_cell_angle_gamma                90.00
_cell_volume                     1920.26(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      31.83

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            19210
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         32.03
_reflns_number_total             5793
_reflns_number_gt                4634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0702P)²+0.3845P] 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         5793
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 -0.00248(3) 0.58118(3) 0.140189(15) 0.03851(10) Uani 1 1 d . . .
O2 O -0.08637(11) 0.57221(11) 0.19042(5) 0.0512(3) Uani 1 1 d . . .
C1 C 0.18554(12) 0.61865(12) 0.17695(6) 0.0350(2) Uani 1 1 d . . .
C6 C 0.29068(13) 0.62489(12) 0.13488(6) 0.0360(2) Uani 1 1 d . . .
C7 C 0.25560(15) 0.59790(13) 0.06649(7) 0.0420(3) Uani 1 1 d . . .
H7 H 0.1604 0.5717 0.0470 0.050 Uiso 1 1 calc R . .
C5 C 0.43856(13) 0.66316(13) 0.16322(7) 0.0405(3) Uani 1 1 d . . .
C18 C -0.06306(13) 0.72402(13) 0.09404(6) 0.0381(2) Uani 1 1 d . . .
C2 C 0.22649(14) 0.65146(12) 0.24289(6) 0.0381(3) Uani 1 1 d . . .
O1 O -0.00782(12) 0.47124(10) 0.09605(5) 0.0511(2) Uani 1 1 d . . .
C12 C 0.12963(14) 0.65838(13) 0.29182(6) 0.0397(3) Uani 1 1 d . . .
C4 C 0.47950(14) 0.69428(14) 0.23129(8) 0.0461(3) Uani 1 1 d . . .
C8 C 0.35831(17) 0.60936(15) 0.02828(8) 0.0500(3) Uani 1 1 d . . .
H8 H 0.3317 0.5920 -0.0165 0.060 Uiso 1 1 calc R . .
C3 C 0.37507(15) 0.68871(15) 0.26845(7) 0.0459(3) Uani 1 1 d . . .
H3 H 0.4025 0.7104 0.3128 0.055 Uiso 1 1 calc R . .
C10 C 0.54195(16) 0.67199(15) 0.12161(8) 0.0517(3) Uani 1 1 d . . .
H10 H 0.6387 0.6955 0.1398 0.062 Uiso 1 1 calc R . .
C19 C -0.10726(15) 0.71978(14) 0.02630(7) 0.0442(3) Uani 1 1 d . . .
H19 H -0.1023 0.6414 0.0037 0.053 Uiso 1 1 calc R . .
C21 C -0.16529(15) 0.95193(15) 0.02519(8) 0.0489(3) Uani 1 1 d . . .
C17 C 0.09557(17) 0.78115(15) 0.31384(7) 0.0494(3) Uani 1 1 d . . .
H17 H 0.1300 0.8568 0.2969 0.059 Uiso 1 1 calc R . .
C20 C -0.15913(16) 0.83405(16) -0.00760(7) 0.0499(3) Uani 1 1 d . . .
H20 H -0.1902 0.8313 -0.0531 0.060 Uiso 1 1 calc R . .
C9 C 0.50287(18) 0.64699(16) 0.05620(9) 0.0553(4) Uani 1 1 d . . .
H9 H 0.5719 0.6549 0.0300 0.066 Uiso 1 1 calc R . .
C23 C -0.07071(17) 0.84056(15) 0.12799(7) 0.0510(3) Uani 1 1 d . . .
H23 H -0.0424 0.8427 0.1736 0.061 Uiso 1 1 calc R . .
C16 C 0.01067(19) 0.79199(19) 0.36083(8) 0.0602(4) Uani 1 1 d . . .
H16 H -0.0130 0.8747 0.3748 0.072 Uiso 1 1 calc R . .
C13 C 0.08128(17) 0.54657(16) 0.31918(7) 0.0495(3) Uani 1 1 d . . .
H13 H 0.1057 0.4635 0.3059 0.059 Uiso 1 1 calc R . .
C14 C -0.00325(18) 0.55824(19) 0.36615(7) 0.0576(4) Uani 1 1 d . . .
H14 H -0.0364 0.4829 0.3839 0.069 Uiso 1 1 calc R . .
C22 C -0.12073(18) 0.95307(16) 0.09328(8) 0.0560(4) Uani 1 1 d . . .
H22 H -0.1248 1.0315 0.1159 0.067 Uiso 1 1 calc R . .
C11 C 0.63416(17) 0.7363(2) 0.26241(10) 0.0662(5) Uani 1 1 d . . .
H11A H 0.6406 0.7545 0.3082 0.099 Uiso 1 1 calc R . .
H11B H 0.6588 0.8142 0.2409 0.099 Uiso 1 1 calc R . .
H11C H 0.7016 0.6670 0.2579 0.099 Uiso 1 1 calc R . .
C24 C -0.2182(2) 1.07663(18) -0.01141(10) 0.0666(5) Uani 1 1 d . . .
H24A H -0.1884 1.0771 -0.0528 0.100 Uiso 1 1 calc R . .
H24B H -0.1762 1.1513 0.0141 0.100 Uiso 1 1 calc R . .
H24C H -0.3236 1.0810 -0.0189 0.100 Uiso 1 1 calc R . .
C15 C -0.03863(19) 0.6802(2) 0.38678(8) 0.0622(4) Uani 1 1 d . . .
H15 H -0.0958 0.6872 0.4182 0.075 Uiso 1 1 calc R . .


_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 O2 1.4342(9) . ?
S1 O1 1.4400(10) . ?
S1 C18 1.7645(13) . ?
S1 C1 1.7936(12) . ?
C1 C2 1.3853(17) . ?
C1 C6 1.4458(15) . ?
C6 C7 1.4185(18) . ?
C6 C5 1.4297(18) . ?
C7 C8 1.3714(17) . ?
C7 H7 0.9300 . ?
C5 C4 1.423(2) . ?
C5 C10 1.4271(17) . ?
C18 C19 1.3834(18) . ?
C18 C23 1.3878(18) . ?
C2 C3 1.4218(18) . ?
C2 C12 1.4980(16) . ?
C12 C13 1.3870(19) . ?
C12 C17 1.3876(19) . ?
C4 C3 1.3652(19) . ?
C4 C11 1.508(2) . ?
C8 C9 1.399(2) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C10 C9 1.357(2) . ?
C10 H10 0.9300 . ?
C19 C20 1.390(2) . ?
C19 H19 0.9300 . ?
C21 C20 1.385(2) . ?
C21 C22 1.390(2) . ?
C21 C24 1.505(2) . ?
C17 C16 1.386(2) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C9 H9 0.9300 . ?
C23 C22 1.378(2) . ?
C23 H23 0.9300 . ?
C16 C15 1.377(3) . ?
C16 H16 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 H15 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
O2 S1 O1 117.77(6) . . ?
O2 S1 C18 106.82(6) . . ?
O1 S1 C18 109.00(6) . . ?
O2 S1 C1 109.50(6) . . ?
O1 S1 C1 109.58(6) . . ?
C18 S1 C1 103.15(6) . . ?
C2 C1 C6 120.74(11) . . ?
C2 C1 S1 120.77(9) . . ?
C6 C1 S1 118.28(9) . . ?
C7 C6 C5 117.56(11) . . ?
C7 C6 C1 123.98(11) . . ?
C5 C6 C1 118.44(11) . . ?
C8 C7 C6 121.75(13) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C4 C5 C10 121.25(13) . . ?
C4 C5 C6 120.12(11) . . ?
C10 C5 C6 118.61(13) . . ?
C19 C18 C23 120.64(13) . . ?
C19 C18 S1 121.40(10) . . ?
C23 C18 S1 117.91(10) . . ?
C1 C2 C3 118.39(11) . . ?
C1 C2 C12 127.39(11) . . ?
C3 C2 C12 114.16(11) . . ?
C13 C12 C17 118.87(12) . . ?
C13 C12 C2 122.35(12) . . ?
C17 C12 C2 118.63(12) . . ?
C3 C4 C5 118.91(12) . . ?
C3 C4 C11 119.75(14) . . ?
C5 C4 C11 121.32(13) . . ?
C7 C8 C9 120.51(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C3 C2 123.37(13) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
C9 C10 C5 121.78(14) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C18 C19 C20 119.19(13) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C20 C21 C22 118.39(14) . . ?
C20 C21 C24 121.35(15) . . ?
C22 C21 C24 120.26(15) . . ?
C16 C17 C12 120.58(14) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C21 C20 C19 121.12(13) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C10 C9 C8 119.78(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C22 C23 C18 119.17(14) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.4 . . ?
C15 C16 C17 119.91(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C14 C13 C12 120.17(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.54(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C23 C22 C21 121.47(14) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C15 C16 119.91(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?

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
O2 S1 C1 C2 -8.58(12) . . . . ?
O1 S1 C1 C2 -139.16(10) . . . . ?
C18 S1 C1 C2 104.86(11) . . . . ?
O2 S1 C1 C6 176.68(9) . . . . ?
O1 S1 C1 C6 46.10(11) . . . . ?
C18 S1 C1 C6 -69.88(10) . . . . ?
C2 C1 C6 C7 -177.41(12) . . . . ?
S1 C1 C6 C7 -2.67(16) . . . . ?
C2 C1 C6 C5 1.22(17) . . . . ?
S1 C1 C6 C5 175.97(9) . . . . ?
C5 C6 C7 C8 -0.81(18) . . . . ?
C1 C6 C7 C8 177.84(12) . . . . ?
C7 C6 C5 C4 178.62(12) . . . . ?
C1 C6 C5 C4 -0.10(18) . . . . ?
C7 C6 C5 C10 -0.04(17) . . . . ?
C1 C6 C5 C10 -178.76(11) . . . . ?
O2 S1 C18 C19 -127.83(11) . . . . ?
O1 S1 C18 C19 0.40(12) . . . . ?
C1 S1 C18 C19 116.79(11) . . . . ?
O2 S1 C18 C23 49.67(12) . . . . ?
O1 S1 C18 C23 177.91(11) . . . . ?
C1 S1 C18 C23 -65.71(12) . . . . ?
C6 C1 C2 C3 -1.29(18) . . . . ?
S1 C1 C2 C3 -175.90(10) . . . . ?
C6 C1 C2 C12 175.86(11) . . . . ?
S1 C1 C2 C12 1.25(18) . . . . ?
C1 C2 C12 C13 76.26(18) . . . . ?
C3 C2 C12 C13 -106.48(15) . . . . ?
C1 C2 C12 C17 -108.25(16) . . . . ?
C3 C2 C12 C17 69.00(17) . . . . ?
C10 C5 C4 C3 177.71(13) . . . . ?
C6 C5 C4 C3 -0.9(2) . . . . ?
C10 C5 C4 C11 -0.7(2) . . . . ?
C6 C5 C4 C11 -179.35(13) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C5 C4 C3 C2 0.9(2) . . . . ?
C11 C4 C3 C2 179.33(15) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C12 C2 C3 C4 -177.28(13) . . . . ?
C4 C5 C10 C9 -177.67(14) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
C23 C18 C19 C20 0.2(2) . . . . ?
S1 C18 C19 C20 177.68(10) . . . . ?
C13 C12 C17 C16 -2.1(2) . . . . ?
C2 C12 C17 C16 -177.70(13) . . . . ?
C22 C21 C20 C19 -1.2(2) . . . . ?
C24 C21 C20 C19 178.61(14) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C5 C10 C9 C8 -1.1(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C19 C18 C23 C22 -1.1(2) . . . . ?
S1 C18 C23 C22 -178.59(12) . . . . ?
C12 C17 C16 C15 1.0(3) . . . . ?
C17 C12 C13 C14 1.9(2) . . . . ?
C2 C12 C13 C14 177.42(13) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C18 C23 C22 C21 0.8(2) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C24 C21 C22 C23 -179.46(15) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C17 C16 C15 C14 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.867
_diffrn_reflns_theta_full        32.03
_diffrn_measured_fraction_theta_full 0.867
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.068
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_141022h
_database_code_depnum_ccdc_archive 'CCDC 1474253'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 O2 S'
_chemical_formula_weight         408.49

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   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                   7.0521(6)
_cell_length_b                   28.030(2)
_cell_length_c                   10.4649(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.0690(10)
_cell_angle_gamma                90.00
_cell_volume                     2036.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    950
_cell_measurement_theta_min      2.9780
_cell_measurement_theta_max      23.8690

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9231
_exptl_absorpt_correction_T_max  0.9444
_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            7408
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.1145
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3601
_reflns_number_gt                1972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0326P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3601
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.39200(16) 0.35209(4) 0.10860(9) 0.0466(3) Uani 1 1 d . . .
O1 O 0.4052(4) 0.32664(10) 0.2291(2) 0.0611(8) Uani 1 1 d . . .
O2 O 0.5668(4) 0.35588(10) 0.0549(2) 0.0590(8) Uani 1 1 d . . .
C1 C 0.3065(5) 0.41128(12) 0.1247(3) 0.0353(9) Uani 1 1 d . . .
C2 C 0.2644(5) 0.42642(13) 0.2415(3) 0.0366(9) Uani 1 1 d . . .
C3 C 0.2306(5) 0.47662(13) 0.2599(3) 0.0362(9) Uani 1 1 d . . .
C4 C 0.2009(6) 0.49395(15) 0.3821(3) 0.0483(11) Uani 1 1 d . . .
H4 H 0.2016 0.4727 0.4505 0.058 Uiso 1 1 calc R . .
C5 C 0.1711(6) 0.54130(15) 0.4005(4) 0.0527(11) Uani 1 1 d . . .
H5 H 0.1500 0.5521 0.4809 0.063 Uiso 1 1 calc R . .
C6 C 0.1722(6) 0.57336(15) 0.3002(4) 0.0570(12) Uani 1 1 d . . .
H6 H 0.1524 0.6056 0.3136 0.068 Uiso 1 1 calc R . .
C7 C 0.2021(6) 0.55783(14) 0.1818(4) 0.0473(10) Uani 1 1 d . . .
H7 H 0.2033 0.5798 0.1153 0.057 Uiso 1 1 calc R . .
C8 C 0.2310(5) 0.50930(13) 0.1585(3) 0.0341(9) Uani 1 1 d . . .
C9 C 0.2560(5) 0.49215(13) 0.0317(3) 0.0345(9) Uani 1 1 d . . .
C10 C 0.2976(5) 0.44339(13) 0.0149(3) 0.0353(9) Uani 1 1 d . . .
C11 C 0.3214(5) 0.42807(14) -0.1098(3) 0.0431(10) Uani 1 1 d . . .
H11 H 0.3472 0.3961 -0.1233 0.052 Uiso 1 1 calc R . .
C12 C 0.3072(5) 0.45936(16) -0.2110(3) 0.0478(11) Uani 1 1 d . . .
H12 H 0.3236 0.4484 -0.2922 0.057 Uiso 1 1 calc R . .
C13 C 0.2688(5) 0.50729(15) -0.1946(3) 0.0474(10) Uani 1 1 d . . .
H13 H 0.2594 0.5283 -0.2641 0.057 Uiso 1 1 calc R . .
C14 C 0.2449(5) 0.52315(14) -0.0749(3) 0.0448(10) Uani 1 1 d . . .
H14 H 0.2207 0.5554 -0.0637 0.054 Uiso 1 1 calc R . .
C15 C 0.2365(7) 0.39433(14) 0.3503(3) 0.0505(11) Uani 1 1 d . . .
C16 C 0.0551(8) 0.37533(15) 0.3515(4) 0.0669(14) Uani 1 1 d . . .
H16 H -0.0441 0.3812 0.2822 0.080 Uiso 1 1 calc R . .
C17 C 0.0205(11) 0.34790(19) 0.4540(6) 0.107(2) Uani 1 1 d . . .
H17 H -0.1011 0.3351 0.4547 0.128 Uiso 1 1 calc R . .
C18 C 0.1695(15) 0.3397(3) 0.5557(7) 0.135(4) Uani 1 1 d . . .
H18 H 0.1478 0.3207 0.6245 0.162 Uiso 1 1 calc R . .
C19 C 0.3445(13) 0.3584(2) 0.5583(5) 0.120(3) Uani 1 1 d . . .
H19 H 0.4424 0.3527 0.6285 0.145 Uiso 1 1 calc R . .
C20 C 0.3794(8) 0.38658(17) 0.4549(4) 0.0811(17) Uani 1 1 d . . .
H20 H 0.5003 0.4001 0.4571 0.097 Uiso 1 1 calc R . .
C21 C 0.2155(6) 0.32344(13) -0.0054(3) 0.0397(9) Uani 1 1 d . . .
C22 C 0.0234(6) 0.33371(14) -0.0149(3) 0.0472(10) Uani 1 1 d . . .
H22 H -0.0156 0.3571 0.0381 0.057 Uiso 1 1 calc R . .
C23 C -0.1135(6) 0.30945(14) -0.1031(3) 0.0530(11) Uani 1 1 d . . .
H23 H -0.2433 0.3169 -0.1090 0.064 Uiso 1 1 calc R . .
C24 C -0.0590(7) 0.27473(15) -0.1814(4) 0.0554(12) Uani 1 1 d . . .
C25 C 0.1348(8) 0.26373(15) -0.1673(4) 0.0632(13) Uani 1 1 d . . .
H25 H 0.1734 0.2393 -0.2171 0.076 Uiso 1 1 calc R . .
C26 C 0.2729(6) 0.28797(14) -0.0814(4) 0.0545(11) Uani 1 1 d . . .
H26 H 0.4027 0.2804 -0.0751 0.065 Uiso 1 1 calc R . .
C27 C -0.2066(7) 0.24955(17) -0.2800(4) 0.0892(17) Uani 1 1 d . . .
H27A H -0.2315 0.2680 -0.3584 0.134 Uiso 1 1 calc R . .
H27B H -0.3238 0.2459 -0.2461 0.134 Uiso 1 1 calc R . .
H27C H -0.1587 0.2187 -0.2984 0.134 Uiso 1 1 calc R . .


_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 1.437(2) . ?
S1 O2 1.445(3) . ?
S1 C21 1.760(4) . ?
S1 C1 1.783(3) . ?
C1 C2 1.375(4) . ?
C1 C10 1.452(4) . ?
C2 C3 1.446(5) . ?
C2 C15 1.491(5) . ?
C3 C8 1.402(4) . ?
C3 C4 1.417(4) . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.364(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.451(4) . ?
C9 C14 1.405(4) . ?
C9 C10 1.415(4) . ?
C10 C11 1.411(4) . ?
C11 C12 1.365(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.370(6) . ?
C15 C16 1.387(6) . ?
C16 C17 1.376(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.337(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.371(5) . ?
C21 C26 1.378(5) . ?
C22 C23 1.392(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(6) . ?
C24 C27 1.507(5) . ?
C25 C26 1.383(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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 O2 116.66(17) . . ?
O1 S1 C21 107.32(17) . . ?
O2 S1 C21 108.67(16) . . ?
O1 S1 C1 110.49(16) . . ?
O2 S1 C1 107.08(16) . . ?
C21 S1 C1 106.13(17) . . ?
C2 C1 C10 121.8(3) . . ?
C2 C1 S1 120.0(3) . . ?
C10 C1 S1 118.1(2) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 C15 124.8(3) . . ?
C3 C2 C15 116.0(3) . . ?
C8 C3 C4 118.6(3) . . ?
C8 C3 C2 120.9(3) . . ?
C4 C3 C2 120.5(3) . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.1(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.9(3) . . ?
C3 C8 C9 119.5(3) . . ?
C7 C8 C9 121.6(3) . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 121.5(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C10 C9 118.0(3) . . ?
C11 C10 C1 123.2(3) . . ?
C9 C10 C1 118.8(3) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.1(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 121.8(4) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
C20 C15 C16 118.9(4) . . ?
C20 C15 C2 121.9(4) . . ?
C16 C15 C2 118.9(4) . . ?
C17 C16 C15 120.7(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 118.6(7) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 121.8(7) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.6(7) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.3(6) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C26 119.7(4) . . ?
C22 C21 S1 121.7(3) . . ?
C26 C21 S1 118.5(3) . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.6(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 118.0(4) . . ?
C23 C24 C27 120.6(4) . . ?
C25 C24 C27 121.4(4) . . ?
C26 C25 C24 122.0(4) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C21 C26 C25 119.0(4) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C1 C2 0.2(4) . . . . ?
O2 S1 C1 C2 -127.8(3) . . . . ?
C21 S1 C1 C2 116.2(3) . . . . ?
O1 S1 C1 C10 175.5(3) . . . . ?
O2 S1 C1 C10 47.5(3) . . . . ?
C21 S1 C1 C10 -68.4(3) . . . . ?
C10 C1 C2 C3 -6.7(5) . . . . ?
S1 C1 C2 C3 168.4(3) . . . . ?
C10 C1 C2 C15 168.7(4) . . . . ?
S1 C1 C2 C15 -16.2(5) . . . . ?
C1 C2 C3 C8 3.2(5) . . . . ?
C15 C2 C3 C8 -172.6(3) . . . . ?
C1 C2 C3 C4 -175.4(3) . . . . ?
C15 C2 C3 C4 8.8(5) . . . . ?
C8 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C5 179.3(4) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C5 C6 C7 C8 0.4(6) . . . . ?
C4 C3 C8 C7 0.1(5) . . . . ?
C2 C3 C8 C7 -178.5(3) . . . . ?
C4 C3 C8 C9 -178.3(3) . . . . ?
C2 C3 C8 C9 3.1(5) . . . . ?
C6 C7 C8 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 177.7(4) . . . . ?
C3 C8 C9 C14 175.8(3) . . . . ?
C7 C8 C9 C14 -2.5(5) . . . . ?
C3 C8 C9 C10 -5.9(5) . . . . ?
C7 C8 C9 C10 175.8(3) . . . . ?
C14 C9 C10 C11 -1.5(5) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C14 C9 C10 C1 -179.2(3) . . . . ?
C8 C9 C10 C1 2.5(5) . . . . ?
C2 C1 C10 C11 -173.6(3) . . . . ?
S1 C1 C10 C11 11.1(5) . . . . ?
C2 C1 C10 C9 3.9(5) . . . . ?
S1 C1 C10 C9 -171.3(3) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C1 C10 C11 C12 178.4(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C9 -0.8(6) . . . . ?
C10 C9 C14 C13 1.5(5) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C1 C2 C15 C20 99.6(5) . . . . ?
C3 C2 C15 C20 -84.8(5) . . . . ?
C1 C2 C15 C16 -86.5(5) . . . . ?
C3 C2 C15 C16 89.1(4) . . . . ?
C20 C15 C16 C17 -2.0(6) . . . . ?
C2 C15 C16 C17 -176.1(4) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C16 C17 C18 C19 1.3(11) . . . . ?
C17 C18 C19 C20 -0.8(12) . . . . ?
C16 C15 C20 C19 2.5(7) . . . . ?
C2 C15 C20 C19 176.4(4) . . . . ?
C18 C19 C20 C15 -1.2(9) . . . . ?
O1 S1 C21 C22 84.5(3) . . . . ?
O2 S1 C21 C22 -148.5(3) . . . . ?
C1 S1 C21 C22 -33.6(3) . . . . ?
O1 S1 C21 C26 -91.8(3) . . . . ?
O2 S1 C21 C26 35.2(3) . . . . ?
C1 S1 C21 C26 150.1(3) . . . . ?
C26 C21 C22 C23 -1.7(6) . . . . ?
S1 C21 C22 C23 -178.0(3) . . . . ?
C21 C22 C23 C24 0.4(6) . . . . ?
C22 C23 C24 C25 1.8(6) . . . . ?
C22 C23 C24 C27 -178.0(4) . . . . ?
C23 C24 C25 C26 -2.8(6) . . . . ?
C27 C24 C25 C26 177.0(4) . . . . ?
C22 C21 C26 C25 0.8(6) . . . . ?
S1 C21 C26 C25 177.2(3) . . . . ?
C24 C25 C26 C21 1.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.053
