# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_SHB2t
_database_code_depnum_ccdc_archive 'CCDC 1481207'
_audit_update_record             
;
2016-05-21 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SHB2t
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 O2 S2'
_chemical_formula_weight         400.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.6533(2)
_cell_length_b                   13.2733(3)
_cell_length_c                   15.1062(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.485(2)
_cell_angle_gamma                90.00
_cell_volume                     1935.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      4.4200
_cell_measurement_theta_max      62.4080

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4195
_exptl_absorpt_correction_T_max  0.6083
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_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            6270
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         62.53
_reflns_number_total             3035
_reflns_number_gt                2505
_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)+(0.0552P)²+0.1162P] 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         3035
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
S2 S 0.16206(6) 0.32199(4) 0.31105(3) 0.06331(19) Uani 1 1 d . . .
S1 S 0.16361(7) 0.21935(5) -0.12906(4) 0.0755(2) Uani 1 1 d . . .
C1 C 0.1433(2) 0.35124(19) -0.13811(13) 0.0653(6) Uani 1 1 d . . .
C13 C 0.1347(2) 0.12017(16) 0.25903(13) 0.0550(5) Uani 1 1 d . . .
O2 O 0.3017(2) 0.19482(15) -0.15656(12) 0.0941(6) Uani 1 1 d . . .
C8 C 0.2587(2) 0.22126(18) 0.04074(15) 0.0665(6) Uani 1 1 d . . .
H8 H 0.3354 0.2545 0.0181 0.080 Uiso 1 1 calc R . .
C23 C 0.1586(2) 0.34248(17) 0.42505(14) 0.0609(5) Uani 1 1 d . . .
C9 C 0.2522(2) 0.19980(18) 0.12940(14) 0.0641(6) Uani 1 1 d . . .
H9 H 0.3240 0.2198 0.1669 0.077 Uiso 1 1 calc R . .
C24 C 0.1464(2) 0.19204(15) 0.32609(13) 0.0527(5) Uani 1 1 d . . .
C19 C 0.1406(2) 0.2589(2) 0.56588(15) 0.0722(6) Uani 1 1 d . . .
H19 H 0.1338 0.2004 0.5995 0.087 Uiso 1 1 calc R . .
O1 O 0.0479(2) 0.17243(17) -0.17292(12) 0.1074(7) Uani 1 1 d . . .
C16 C 0.1279(2) 0.06410(17) 0.43869(15) 0.0650(6) Uani 1 1 d . . .
H16 H 0.1272 0.0447 0.4978 0.078 Uiso 1 1 calc R . .
C10 C 0.1391(2) 0.14828(16) 0.16386(14) 0.0578(5) Uani 1 1 d . . .
C17 C 0.1413(2) 0.16583(16) 0.41609(13) 0.0551(5) Uani 1 1 d . . .
C14 C 0.1172(2) 0.02074(17) 0.28450(16) 0.0653(6) Uani 1 1 d . . .
H14 H 0.1061 -0.0286 0.2413 0.078 Uiso 1 1 calc R . .
C7 C 0.1512(2) 0.19342(17) -0.01484(14) 0.0633(6) Uani 1 1 d . . .
C18 C 0.1476(2) 0.25274(17) 0.47345(13) 0.0579(5) Uani 1 1 d . . .
C15 C 0.1157(2) -0.00662(17) 0.37333(17) 0.0700(6) Uani 1 1 d . . .
H15 H 0.1064 -0.0742 0.3885 0.084 Uiso 1 1 calc R . .
C6 C 0.2535(2) 0.40843(19) -0.16614(14) 0.0679(6) Uani 1 1 d . . .
H6 H 0.3395 0.3788 -0.1751 0.081 Uiso 1 1 calc R . .
C12 C 0.0373(3) 0.1435(2) 0.01795(16) 0.0729(6) Uani 1 1 d . . .
H12 H -0.0357 0.1257 -0.0195 0.087 Uiso 1 1 calc R . .
C11 C 0.0328(2) 0.12015(19) 0.10691(15) 0.0708(6) Uani 1 1 d . . .
H11 H -0.0428 0.0850 0.1289 0.085 Uiso 1 1 calc R . .
C22 C 0.1633(3) 0.43576(19) 0.46728(17) 0.0767(7) Uani 1 1 d . . .
H22 H 0.1716 0.4949 0.4348 0.092 Uiso 1 1 calc R . .
C5 C 0.2352(3) 0.5094(2) -0.18064(16) 0.0786(7) Uani 1 1 d . . .
H5 H 0.3087 0.5479 -0.2012 0.094 Uiso 1 1 calc R . .
C21 C 0.1555(3) 0.4382(2) 0.55799(19) 0.0872(8) Uani 1 1 d . . .
H21 H 0.1581 0.5000 0.5871 0.105 Uiso 1 1 calc R . .
C4 C 0.1120(3) 0.5538(3) -0.1656(2) 0.1017(10) Uani 1 1 d . . .
H4 H 0.1010 0.6224 -0.1759 0.122 Uiso 1 1 calc R . .
C20 C 0.1438(3) 0.3506(2) 0.60669(18) 0.0846(8) Uani 1 1 d . . .
H20 H 0.1379 0.3542 0.6680 0.101 Uiso 1 1 calc R . .
C2 C 0.0173(3) 0.3954(3) -0.1220(2) 0.1029(10) Uani 1 1 d . . .
H2 H -0.0570 0.3569 -0.1027 0.123 Uiso 1 1 calc R . .
C3 C 0.0030(3) 0.4978(3) -0.1350(3) 0.1278(14) Uani 1 1 d . . .
H3 H -0.0810 0.5290 -0.1230 0.153 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
S2 C24 1.747(2) . ?
S2 C23 1.744(2) . ?
S1 O2 1.437(2) . ?
S1 O1 1.436(2) . ?
S1 C7 1.764(2) . ?
S1 C1 1.767(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.376(3) . ?
C13 C14 1.385(3) . ?
C13 C24 1.395(3) . ?
C13 C10 1.486(3) . ?
C8 C9 1.371(3) . ?
C8 C7 1.380(3) . ?
C8 H8 0.9300 . ?
C23 C22 1.393(3) . ?
C23 C18 1.402(3) . ?
C9 C10 1.393(3) . ?
C9 H9 0.9300 . ?
C24 C17 1.405(3) . ?
C19 C20 1.365(4) . ?
C19 C18 1.401(3) . ?
C19 H19 0.9300 . ?
C16 C15 1.367(3) . ?
C16 C17 1.399(3) . ?
C16 H16 0.9300 . ?
C10 C11 1.385(3) . ?
C17 C18 1.444(3) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C7 C12 1.380(3) . ?
C15 H15 0.9300 . ?
C6 C5 1.369(4) . ?
C6 H6 0.9300 . ?
C12 C11 1.380(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C22 C21 1.373(4) . ?
C22 H22 0.9300 . ?
C5 C4 1.348(4) . ?
C5 H5 0.9300 . ?
C21 C20 1.381(4) . ?
C21 H21 0.9300 . ?
C4 C3 1.371(5) . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 H3 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
C24 S2 C23 91.32(10) . . ?
O2 S1 O1 119.22(13) . . ?
O2 S1 C7 108.02(12) . . ?
O1 S1 C7 107.92(12) . . ?
O2 S1 C1 107.73(12) . . ?
O1 S1 C1 107.99(13) . . ?
C7 S1 C1 105.10(10) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 S1 120.4(2) . . ?
C6 C1 S1 119.0(2) . . ?
C14 C13 C24 117.32(19) . . ?
C14 C13 C10 120.82(19) . . ?
C24 C13 C10 121.86(18) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C22 C23 C18 121.2(2) . . ?
C22 C23 S2 126.15(19) . . ?
C18 C23 S2 112.62(16) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C13 C24 C17 122.01(19) . . ?
C13 C24 S2 125.96(15) . . ?
C17 C24 S2 111.98(16) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 C13 120.42(19) . . ?
C9 C10 C13 120.89(19) . . ?
C16 C17 C24 118.6(2) . . ?
C16 C17 C18 128.9(2) . . ?
C24 C17 C18 112.42(18) . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C8 C7 C12 120.5(2) . . ?
C8 C7 S1 119.07(17) . . ?
C12 C7 S1 120.38(17) . . ?
C19 C18 C23 118.4(2) . . ?
C19 C18 C17 130.0(2) . . ?
C23 C18 C17 111.64(18) . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C11 C12 C7 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C21 C22 C23 118.4(2) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?

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 175.3(2) . . . . ?
O1 S1 C1 C2 45.3(3) . . . . ?
C7 S1 C1 C2 -69.7(2) . . . . ?
O2 S1 C1 C6 -1.2(2) . . . . ?
O1 S1 C1 C6 -131.16(18) . . . . ?
C7 S1 C1 C6 113.83(18) . . . . ?
C24 S2 C23 C22 -178.2(2) . . . . ?
C24 S2 C23 C18 0.78(17) . . . . ?
C7 C8 C9 C10 1.3(4) . . . . ?
C14 C13 C24 C17 0.2(3) . . . . ?
C10 C13 C24 C17 179.53(18) . . . . ?
C14 C13 C24 S2 -177.24(16) . . . . ?
C10 C13 C24 S2 2.0(3) . . . . ?
C23 S2 C24 C13 176.64(19) . . . . ?
C23 S2 C24 C17 -1.06(16) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C8 C9 C10 C13 176.8(2) . . . . ?
C14 C13 C10 C11 54.0(3) . . . . ?
C24 C13 C10 C11 -125.3(2) . . . . ?
C14 C13 C10 C9 -123.5(2) . . . . ?
C24 C13 C10 C9 57.3(3) . . . . ?
C15 C16 C17 C24 -2.0(3) . . . . ?
C15 C16 C17 C18 176.2(2) . . . . ?
C13 C24 C17 C16 1.8(3) . . . . ?
S2 C24 C17 C16 179.57(16) . . . . ?
C13 C24 C17 C18 -176.71(18) . . . . ?
S2 C24 C17 C18 1.1(2) . . . . ?
C24 C13 C14 C15 -2.0(3) . . . . ?
C10 C13 C14 C15 178.7(2) . . . . ?
C9 C8 C7 C12 -0.4(4) . . . . ?
C9 C8 C7 S1 -178.60(18) . . . . ?
O2 S1 C7 C8 42.9(2) . . . . ?
O1 S1 C7 C8 173.1(2) . . . . ?
C1 S1 C7 C8 -71.9(2) . . . . ?
O2 S1 C7 C12 -135.3(2) . . . . ?
O1 S1 C7 C12 -5.1(3) . . . . ?
C1 S1 C7 C12 109.9(2) . . . . ?
C20 C19 C18 C23 0.3(3) . . . . ?
C20 C19 C18 C17 -177.6(2) . . . . ?
C22 C23 C18 C19 0.4(3) . . . . ?
S2 C23 C18 C19 -178.57(16) . . . . ?
C22 C23 C18 C17 178.7(2) . . . . ?
S2 C23 C18 C17 -0.3(2) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C24 C17 C18 C19 177.5(2) . . . . ?
C16 C17 C18 C23 -178.8(2) . . . . ?
C24 C17 C18 C23 -0.5(2) . . . . ?
C17 C16 C15 C14 0.3(3) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
S1 C1 C6 C5 174.42(17) . . . . ?
C8 C7 C12 C11 -1.0(4) . . . . ?
S1 C7 C12 C11 177.2(2) . . . . ?
C7 C12 C11 C10 1.6(4) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C13 C10 C11 C12 -178.3(2) . . . . ?
C18 C23 C22 C21 -0.7(4) . . . . ?
S2 C23 C22 C21 178.13(19) . . . . ?
C1 C6 C5 C4 1.8(4) . . . . ?
C23 C22 C21 C20 0.3(4) . . . . ?
C6 C5 C4 C3 0.2(5) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
S1 C1 C2 C3 -176.0(3) . . . . ?
C5 C4 C3 C2 -1.9(6) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        62.53
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_SDB2t
_database_code_depnum_ccdc_archive 'CCDC 1481208'
_audit_update_record             
;
2016-05-21 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SDB2t
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H24 Cl2 O2 S3'
_chemical_formula_weight         667.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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                   9.3865(3)
_cell_length_b                   12.1945(3)
_cell_length_c                   26.4154(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.268(2)
_cell_angle_gamma                90.00
_cell_volume                     3015.22(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.83(10)
_cell_measurement_reflns_used    2441
_cell_measurement_theta_min      3.3240
_cell_measurement_theta_max      66.7430

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    4.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2939
_exptl_absorpt_correction_T_max  0.6577
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294.83(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_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            5373
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         66.86
_reflns_number_total             2630
_reflns_number_gt                2219
_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)+(0.0552P)²+1.8192P] 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         2630
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0928
_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
S2 S 0.18600(6) 0.38870(5) 0.48949(2) 0.02774(17) Uani 1 1 d . . .
S1 S 0.0000 0.24913(6) 0.2500 0.02127(19) Uani 1 2 d S . .
O1 O 0.11578(17) 0.18952(13) 0.22993(5) 0.0283(4) Uani 1 1 d . . .
C7 C 0.2608(2) 0.54107(18) 0.41591(8) 0.0232(5) Uani 1 1 d . . .
C11 C 0.3263(2) 0.57302(19) 0.50642(8) 0.0232(5) Uani 1 1 d . . .
C13 C 0.3632(3) 0.5618(2) 0.60381(8) 0.0287(5) Uani 1 1 d . . .
H13 H 0.4107 0.6286 0.6071 0.034 Uiso 1 1 calc R . .
C1 C 0.0733(2) 0.33886(17) 0.29761(7) 0.0197(4) Uani 1 1 d . . .
C15 C 0.2716(3) 0.3992(2) 0.64200(8) 0.0309(6) Uani 1 1 d . . .
H15 H 0.2589 0.3582 0.6710 0.037 Uiso 1 1 calc R . .
C6 C -0.0071(2) 0.36675(18) 0.33796(8) 0.0209(4) Uani 1 1 d . . .
H6 H -0.0997 0.3405 0.3394 0.025 Uiso 1 1 calc R . .
C5 C 0.0534(2) 0.43410(17) 0.37584(8) 0.0215(5) Uani 1 1 d . . .
H5 H 0.0003 0.4535 0.4028 0.026 Uiso 1 1 calc R . .
C8 C 0.3344(2) 0.63665(19) 0.40567(8) 0.0278(5) Uani 1 1 d . . .
H8 H 0.3392 0.6588 0.3721 0.033 Uiso 1 1 calc R . .
C3 C 0.2679(2) 0.44812(19) 0.33195(8) 0.0254(5) Uani 1 1 d . . .
H3 H 0.3586 0.4774 0.3294 0.030 Uiso 1 1 calc R . .
C12 C 0.3139(2) 0.52341(19) 0.55588(8) 0.0239(5) Uani 1 1 d . . .
C2 C 0.2095(2) 0.38034(19) 0.29401(8) 0.0242(5) Uani 1 1 d . . .
H2 H 0.2610 0.3628 0.2664 0.029 Uiso 1 1 calc R . .
C4 C 0.1925(2) 0.47344(17) 0.37426(8) 0.0209(5) Uani 1 1 d . . .
C18 C 0.2587(2) 0.51044(17) 0.46709(8) 0.0223(5) Uani 1 1 d . . .
C10 C 0.3970(3) 0.66926(19) 0.49461(8) 0.0281(5) Uani 1 1 d . . .
H10 H 0.4409 0.7124 0.5203 0.034 Uiso 1 1 calc R . .
C9 C 0.4012(3) 0.6999(2) 0.44434(9) 0.0318(5) Uani 1 1 d . . .
H9 H 0.4492 0.7635 0.4363 0.038 Uiso 1 1 calc R . .
C14 C 0.3410(2) 0.4996(2) 0.64647(8) 0.0309(6) Uani 1 1 d . . .
H14 H 0.3730 0.5255 0.6784 0.037 Uiso 1 1 calc R . .
C17 C 0.2425(2) 0.42227(19) 0.55212(8) 0.0247(5) Uani 1 1 d . . .
C16 C 0.2210(3) 0.3593(2) 0.59496(8) 0.0295(5) Uani 1 1 d . . .
H16 H 0.1739 0.2922 0.5920 0.035 Uiso 1 1 calc R . .
Cl Cl 0.04346(7) 0.72185(7) 0.30408(3) 0.0485(2) Uani 1 1 d . . .
C19 C 0.0000 0.6421(3) 0.2500 0.0614(14) Uani 1 2 d S . .
H19A H -0.0804 0.5953 0.2562 0.074 Uiso 0.50 1 calc PR . .
H19B H 0.0804 0.5953 0.2438 0.074 Uiso 0.50 1 calc PR . .


_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
S2 C17 1.748(2) . ?
S2 C18 1.755(2) . ?
S1 O1 1.4409(15) 2 ?
S1 O1 1.4409(15) . ?
S1 C1 1.768(2) . ?
S1 C1 1.768(2) 2 ?
C7 C8 1.392(3) . ?
C7 C18 1.404(3) . ?
C7 C4 1.482(3) . ?
C11 C10 1.395(3) . ?
C11 C18 1.402(3) . ?
C11 C12 1.452(3) . ?
C13 C14 1.387(3) . ?
C13 C12 1.396(3) . ?
C13 H13 0.9300 . ?
C1 C2 1.384(3) . ?
C1 C6 1.393(3) . ?
C15 C16 1.385(3) . ?
C15 C14 1.387(4) . ?
C15 H15 0.9300 . ?
C6 C5 1.383(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.395(3) . ?
C5 H5 0.9300 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9300 . ?
C3 C2 1.381(3) . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
C12 C17 1.404(3) . ?
C2 H2 0.9300 . ?
C10 C9 1.383(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C14 H14 0.9300 . ?
C17 C16 1.395(3) . ?
C16 H16 0.9300 . ?
Cl C19 1.751(2) . ?
C19 Cl 1.751(2) 2 ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C17 S2 C18 91.31(10) . . ?
O1 S1 O1 119.41(14) 2 . ?
O1 S1 C1 108.36(9) 2 . ?
O1 S1 C1 108.03(9) . . ?
O1 S1 C1 108.03(9) 2 2 ?
O1 S1 C1 108.36(9) . 2 ?
C1 S1 C1 103.50(13) . 2 ?
C8 C7 C18 116.9(2) . . ?
C8 C7 C4 121.01(19) . . ?
C18 C7 C4 122.04(19) . . ?
C10 C11 C18 119.24(19) . . ?
C10 C11 C12 128.6(2) . . ?
C18 C11 C12 112.18(19) . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 S1 119.34(15) . . ?
C6 C1 S1 119.40(17) . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C6 C5 C4 121.15(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 129.3(2) . . ?
C17 C12 C11 111.87(19) . . ?
C3 C2 C1 119.19(19) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 C7 121.57(18) . . ?
C3 C4 C7 119.9(2) . . ?
C11 C18 C7 122.1(2) . . ?
C11 C18 S2 112.11(16) . . ?
C7 C18 S2 125.68(17) . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C17 C12 121.6(2) . . ?
C16 C17 S2 125.94(19) . . ?
C12 C17 S2 112.48(16) . . ?
C15 C16 C17 118.3(2) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
Cl C19 Cl 112.5(2) . 2 ?
Cl C19 H19A 109.1 . . ?
Cl C19 H19A 109.1 2 . ?
Cl C19 H19B 109.1 . . ?
Cl C19 H19B 109.1 2 . ?
H19A C19 H19B 107.8 . . ?

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 160.67(17) 2 . . . ?
O1 S1 C1 C2 30.0(2) . . . . ?
C1 S1 C1 C2 -84.80(17) 2 . . . ?
O1 S1 C1 C6 -19.5(2) 2 . . . ?
O1 S1 C1 C6 -150.22(17) . . . . ?
C1 S1 C1 C6 95.02(18) 2 . . . ?
C2 C1 C6 C5 -2.3(3) . . . . ?
S1 C1 C6 C5 177.86(16) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C18 C7 C8 C9 -0.9(3) . . . . ?
C4 C7 C8 C9 -178.9(2) . . . . ?
C14 C13 C12 C17 0.1(3) . . . . ?
C14 C13 C12 C11 -179.1(2) . . . . ?
C10 C11 C12 C13 3.3(4) . . . . ?
C18 C11 C12 C13 -178.2(2) . . . . ?
C10 C11 C12 C17 -175.9(2) . . . . ?
C18 C11 C12 C17 2.6(3) . . . . ?
C4 C3 C2 C1 1.3(3) . . . . ?
C6 C1 C2 C3 1.9(3) . . . . ?
S1 C1 C2 C3 -178.32(17) . . . . ?
C6 C5 C4 C3 3.4(3) . . . . ?
C6 C5 C4 C7 -176.9(2) . . . . ?
C2 C3 C4 C5 -3.8(3) . . . . ?
C2 C3 C4 C7 176.4(2) . . . . ?
C8 C7 C4 C5 -133.6(2) . . . . ?
C18 C7 C4 C5 48.6(3) . . . . ?
C8 C7 C4 C3 46.1(3) . . . . ?
C18 C7 C4 C3 -131.7(2) . . . . ?
C10 C11 C18 C7 0.5(3) . . . . ?
C12 C11 C18 C7 -178.1(2) . . . . ?
C10 C11 C18 S2 176.27(18) . . . . ?
C12 C11 C18 S2 -2.3(2) . . . . ?
C8 C7 C18 C11 0.5(3) . . . . ?
C4 C7 C18 C11 178.4(2) . . . . ?
C8 C7 C18 S2 -174.63(18) . . . . ?
C4 C7 C18 S2 3.3(3) . . . . ?
C17 S2 C18 C11 1.18(18) . . . . ?
C17 S2 C18 C7 176.8(2) . . . . ?
C18 C11 C10 C9 -1.2(4) . . . . ?
C12 C11 C10 C9 177.2(2) . . . . ?
C11 C10 C9 C8 0.8(4) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C16 C15 C14 C13 -0.9(4) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 178.8(2) . . . . ?
C13 C12 C17 S2 179.01(17) . . . . ?
C11 C12 C17 S2 -1.7(2) . . . . ?
C18 S2 C17 C16 179.8(2) . . . . ?
C18 S2 C17 C12 0.33(18) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C12 C17 C16 C15 0.3(3) . . . . ?
S2 C17 C16 C15 -179.18(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        66.86
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.056
