# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3mem
_database_code_depnum_ccdc_archive 'CCDC 1411472'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 O2 S2'
_chemical_formula_sum            'C14 H20 O2 S2'
_chemical_formula_weight         284.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  P2ac2ab

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

_cell_length_a                   10.1194(14)
_cell_length_b                   11.6313(16)
_cell_length_c                   12.1672(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1432.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.122
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.0
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            13875
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2511
_reflns_number_gt                2277
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.0414P] 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
_chemical_absolute_configuration syn
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19350(7) 0.70595(6) 0.03270(5) 0.0416(2) Uani 1 1 d . . .
S2 S 0.27385(8) 0.90845(6) 0.17128(6) 0.0466(2) Uani 1 1 d . . .
O1 O 0.21287(19) 0.63199(15) 0.48791(14) 0.0410(5) Uani 1 1 d . . .
O2 O 0.1770(3) 0.7601(2) 0.6217(2) 0.0677(7) Uani 1 1 d . . .
C1 C 0.2810(3) 0.7862(3) -0.0720(2) 0.0508(7) Uani 1 1 d . . .
H1A H 0.3725 0.7613 -0.0726 0.061 Uiso 1 1 calc R . .
H1B H 0.2432 0.7676 -0.1430 0.061 Uiso 1 1 calc R . .
C2 C 0.2775(3) 0.9148(3) -0.0571(2) 0.0565(8) Uani 1 1 d . . .
H2A H 0.3163 0.9511 -0.1212 0.068 Uiso 1 1 calc R . .
H2B H 0.1862 0.9397 -0.0521 0.068 Uiso 1 1 calc R . .
C3 C 0.3505(3) 0.9539(3) 0.0441(3) 0.0506(7) Uani 1 1 d . . .
H3A H 0.3560 1.0372 0.0435 0.061 Uiso 1 1 calc R . .
H3B H 0.4400 0.9240 0.0415 0.061 Uiso 1 1 calc R . .
C4 C 0.2753(3) 0.7516(2) 0.16044(19) 0.0327(6) Uani 1 1 d . . .
C5 C 0.4148(2) 0.7037(2) 0.1701(2) 0.0388(6) Uani 1 1 d . . .
H5A H 0.4630 0.7205 0.1031 0.047 Uiso 1 1 calc R . .
H5B H 0.4599 0.7417 0.2304 0.047 Uiso 1 1 calc R . .
C6 C 0.4158(3) 0.5752(3) 0.1897(2) 0.0451(7) Uani 1 1 d . . .
H6A H 0.5063 0.5488 0.1964 0.054 Uiso 1 1 calc R . .
H6B H 0.3762 0.5365 0.1272 0.054 Uiso 1 1 calc R . .
C7 C 0.1896(3) 0.7127(2) 0.2577(2) 0.0355(6) Uani 1 1 d . . .
H7A H 0.0984 0.7312 0.2408 0.043 Uiso 1 1 calc R . .
H7B H 0.2145 0.7581 0.3213 0.043 Uiso 1 1 calc R . .
C8 C 0.3399(3) 0.5443(2) 0.2933(2) 0.0428(7) Uani 1 1 d . . .
H8A H 0.3837 0.5785 0.3562 0.051 Uiso 1 1 calc R . .
H8B H 0.3414 0.4615 0.3028 0.051 Uiso 1 1 calc R . .
C9 C 0.1960(3) 0.5852(2) 0.29035(19) 0.0350(6) Uani 1 1 d . . .
C10 C 0.1142(3) 0.5069(3) 0.2152(2) 0.0527(8) Uani 1 1 d . . .
H10A H 0.0272 0.5386 0.2065 0.079 Uiso 1 1 calc R . .
H10B H 0.1079 0.4318 0.2474 0.079 Uiso 1 1 calc R . .
H10C H 0.1562 0.5014 0.1447 0.079 Uiso 1 1 calc R . .
C11 C 0.1360(3) 0.5722(2) 0.4063(2) 0.0400(7) Uani 1 1 d . . .
H11 H 0.1345 0.4903 0.4253 0.048 Uiso 1 1 calc R . .
C12 C 0.0010(3) 0.6197(3) 0.4221(3) 0.0510(8) Uani 1 1 d . . .
H12 H -0.0727 0.5993 0.3808 0.061 Uiso 1 1 calc R . .
C13 C 0.0010(3) 0.6943(3) 0.5025(3) 0.0552(8) Uani 1 1 d . . .
H13 H -0.0724 0.7349 0.5271 0.066 Uiso 1 1 calc R . .
C14 C 0.1334(3) 0.7038(3) 0.5474(2) 0.0463(7) Uani 1 1 d . . .


_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 C1 1.810(3) . ?
S1 C4 1.839(2) . ?
S2 C3 1.810(3) . ?
S2 C4 1.829(3) . ?
O1 C14 1.367(3) . ?
O1 C11 1.440(3) . ?
O2 C14 1.201(4) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.507(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.522(4) . ?
C4 C7 1.535(3) . ?
C5 C6 1.513(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.520(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C9 1.536(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.532(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.534(4) . ?
C9 C11 1.544(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.486(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.307(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.451(4) . ?
C13 H13 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
C1 S1 C4 103.03(13) . . ?
C3 S2 C4 103.08(13) . . ?
C14 O1 C11 110.0(2) . . ?
C2 C1 S1 114.6(2) . . ?
C2 C1 H1A 108.6 . . ?
S1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
S1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 112.7(2) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 S2 113.6(2) . . ?
C2 C3 H3A 108.9 . . ?
S2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
S2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C7 110.9(2) . . ?
C5 C4 S2 111.53(18) . . ?
C7 C4 S2 103.52(16) . . ?
C5 C4 S1 112.14(17) . . ?
C7 C4 S1 108.20(17) . . ?
S2 C4 S1 110.20(13) . . ?
C6 C5 C4 112.3(2) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C8 111.2(2) . . ?
C5 C6 H6A 109.4 . . ?
C8 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C8 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C4 C7 C9 117.4(2) . . ?
C4 C7 H7A 108.0 . . ?
C9 C7 H7A 108.0 . . ?
C4 C7 H7B 108.0 . . ?
C9 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
C6 C8 C9 112.8(2) . . ?
C6 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C6 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 110.0(2) . . ?
C8 C9 C7 110.2(2) . . ?
C10 C9 C7 113.4(2) . . ?
C8 C9 C11 108.8(2) . . ?
C10 C9 C11 105.9(2) . . ?
C7 C9 C11 108.3(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C12 103.2(2) . . ?
O1 C11 C9 111.7(2) . . ?
C12 C11 C9 116.3(2) . . ?
O1 C11 H11 108.4 . . ?
C12 C11 H11 108.4 . . ?
C9 C11 H11 108.4 . . ?
C13 C12 C11 110.1(3) . . ?
C13 C12 H12 125.0 . . ?
C11 C12 H12 125.0 . . ?
C12 C13 C14 109.4(3) . . ?
C12 C13 H13 125.3 . . ?
C14 C13 H13 125.3 . . ?
O2 C14 O1 121.0(3) . . ?
O2 C14 C13 131.6(3) . . ?
O1 C14 C13 107.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 -57.9(2) . . . . ?
S1 C1 C2 C3 66.1(3) . . . . ?
C1 C2 C3 S2 -66.9(3) . . . . ?
C4 S2 C3 C2 60.0(2) . . . . ?
C3 S2 C4 C5 70.1(2) . . . . ?
C3 S2 C4 C7 -170.60(17) . . . . ?
C3 S2 C4 S1 -55.08(16) . . . . ?
C1 S1 C4 C5 -70.9(2) . . . . ?
C1 S1 C4 C7 166.52(18) . . . . ?
C1 S1 C4 S2 53.99(17) . . . . ?
C7 C4 C5 C6 51.0(3) . . . . ?
S2 C4 C5 C6 165.80(17) . . . . ?
S1 C4 C5 C6 -70.1(2) . . . . ?
C4 C5 C6 C8 -58.2(3) . . . . ?
C5 C4 C7 C9 -46.0(3) . . . . ?
S2 C4 C7 C9 -165.74(19) . . . . ?
S1 C4 C7 C9 77.3(2) . . . . ?
C5 C6 C8 C9 57.9(3) . . . . ?
C6 C8 C9 C10 75.7(3) . . . . ?
C6 C8 C9 C7 -50.0(3) . . . . ?
C6 C8 C9 C11 -168.7(2) . . . . ?
C4 C7 C9 C8 45.3(3) . . . . ?
C4 C7 C9 C10 -78.5(3) . . . . ?
C4 C7 C9 C11 164.2(2) . . . . ?
C14 O1 C11 C12 1.6(3) . . . . ?
C14 O1 C11 C9 127.3(2) . . . . ?
C8 C9 C11 O1 55.5(3) . . . . ?
C10 C9 C11 O1 173.7(2) . . . . ?
C7 C9 C11 O1 -64.3(3) . . . . ?
C8 C9 C11 C12 173.6(2) . . . . ?
C10 C9 C11 C12 -68.2(3) . . . . ?
C7 C9 C11 C12 53.7(3) . . . . ?
O1 C11 C12 C13 -1.0(3) . . . . ?
C9 C11 C12 C13 -123.6(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C11 O1 C14 O2 178.2(3) . . . . ?
C11 O1 C14 C13 -1.7(3) . . . . ?
C12 C13 C14 O2 -178.9(3) . . . . ?
C12 C13 C14 O1 1.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_65_0m
_database_code_depnum_ccdc_archive 'CCDC 1411484'
_audit_update_record             
;
2015-07-08 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 O2 S2'
_chemical_formula_sum            'C13 H18 O2 S2'
_chemical_formula_weight         270.39
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.6349(2)
_cell_length_b                   8.9609(3)
_cell_length_c                   21.6859(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1289.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7970
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      36.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8405
_exptl_absorpt_correction_T_max  0.8928
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8835
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2245
_reflns_number_gt                2215
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0287P)²+0.4438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_number_reflns         2245
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
O1 O -0.1979(2) 0.72240(15) 0.06958(6) 0.0219(3) Uani 1 1 d . . .
C2 C -0.2569(3) 0.8218(2) 0.11409(9) 0.0220(4) Uani 1 1 d . . .
C3 C -0.0789(3) 0.9030(2) 0.13524(10) 0.0235(4) Uani 1 1 d . . .
H3 H -0.0769 0.9776 0.1664 0.028 Uiso 1 1 calc R . .
C4 C 0.0796(3) 0.8551(2) 0.10356(10) 0.0218(4) Uani 1 1 d . . .
H4 H 0.2135 0.8905 0.1087 0.026 Uiso 1 1 calc R . .
C5 C 0.0175(3) 0.7379(2) 0.05885(9) 0.0199(4) Uani 1 1 d . . .
H5 H 0.0386 0.7768 0.0161 0.024 Uiso 1 1 calc R . .
O6 O -0.4311(2) 0.83262(17) 0.12908(7) 0.0312(4) Uani 1 1 d . . .
S1' S 0.14668(7) 0.30225(5) 0.21161(2) 0.02037(12) Uani 1 1 d . . .
C2' C 0.3142(3) 0.1460(2) 0.22462(9) 0.0227(4) Uani 1 1 d . . .
H2'A H 0.2845 0.1026 0.2656 0.027 Uiso 1 1 calc R . .
H2'B H 0.2863 0.0684 0.1933 0.027 Uiso 1 1 calc R . .
C3' C 0.5367(3) 0.1865(2) 0.22190(9) 0.0244(4) Uani 1 1 d . . .
H3'A H 0.5644 0.2666 0.2522 0.029 Uiso 1 1 calc R . .
H3'B H 0.6178 0.0983 0.2337 0.029 Uiso 1 1 calc R . .
C4' C 0.6010(3) 0.2385(2) 0.15832(9) 0.0223(4) Uani 1 1 d . . .
H4'A H 0.5630 0.1611 0.1279 0.027 Uiso 1 1 calc R . .
H4'B H 0.7496 0.2477 0.1577 0.027 Uiso 1 1 calc R . .
S5' S 0.49245(7) 0.41530(5) 0.13426(2) 0.01892(12) Uani 1 1 d . . .
C6' C 0.2220(3) 0.3721(2) 0.13580(9) 0.0158(4) Uani 1 1 d . . .
C7' C 0.1090(3) 0.5217(2) 0.12935(9) 0.0180(4) Uani 1 1 d . . .
H7'A H -0.0349 0.5060 0.1395 0.022 Uiso 1 1 calc R . .
H7'B H 0.1647 0.5937 0.1595 0.022 Uiso 1 1 calc R . .
C8' C 0.1245(3) 0.5886(2) 0.06469(8) 0.0176(4) Uani 1 1 d . . .
H8' H 0.2707 0.6067 0.0563 0.021 Uiso 1 1 calc R . .
C9' C 0.0506(3) 0.4760(2) 0.01678(9) 0.0211(4) Uani 1 1 d . . .
H9'A H -0.0925 0.4515 0.0247 0.025 Uiso 1 1 calc R . .
H9'B H 0.0605 0.5202 -0.0250 0.025 Uiso 1 1 calc R . .
C10' C 0.1768(3) 0.3347(2) 0.01979(9) 0.0207(4) Uani 1 1 d . . .
H10B H 0.3190 0.3589 0.0102 0.025 Uiso 1 1 calc R . .
H10A H 0.1281 0.2627 -0.0115 0.025 Uiso 1 1 calc R . .
C11' C 0.1642(3) 0.2637(2) 0.08402(8) 0.0175(4) Uani 1 1 d . . .
H11A H 0.0249 0.2279 0.0911 0.021 Uiso 1 1 calc R . .
H11B H 0.2550 0.1761 0.0855 0.021 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
O1 C2 1.371(2) . ?
O1 C5 1.454(2) . ?
C2 O6 1.204(2) . ?
C2 C3 1.461(3) . ?
C3 C4 1.328(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.488(3) . ?
C4 H4 0.9500 . ?
C5 C8' 1.520(3) . ?
C5 H5 1.0000 . ?
S1' C2' 1.8097(19) . ?
S1' C6' 1.8287(19) . ?
C2' C3' 1.521(3) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3' C4' 1.517(3) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C4' S5' 1.816(2) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
S5' C6' 1.8360(18) . ?
C6' C11' 1.533(2) . ?
C6' C7' 1.542(2) . ?
C7' C8' 1.529(3) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C8' C9' 1.529(3) . ?
C8' H8' 1.0000 . ?
C9' C10' 1.519(3) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C10' C11' 1.534(3) . ?
C10' H10B 0.9900 . ?
C10' H10A 0.9900 . ?
C11' H11A 0.9900 . ?
C11' H11B 0.9900 . ?

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 O1 C5 109.36(15) . . ?
O6 C2 O1 121.11(19) . . ?
O6 C2 C3 130.6(2) . . ?
O1 C2 C3 108.29(16) . . ?
C4 C3 C2 108.45(18) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 C5 110.26(18) . . ?
C3 C4 H4 124.9 . . ?
C5 C4 H4 124.9 . . ?
O1 C5 C4 103.62(16) . . ?
O1 C5 C8' 111.21(14) . . ?
C4 C5 C8' 115.94(16) . . ?
O1 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C8' C5 H5 108.6 . . ?
C2' S1' C6' 103.71(9) . . ?
C3' C2' S1' 113.91(13) . . ?
C3' C2' H2'A 108.8 . . ?
S1' C2' H2'A 108.8 . . ?
C3' C2' H2'B 108.8 . . ?
S1' C2' H2'B 108.8 . . ?
H2'A C2' H2'B 107.7 . . ?
C4' C3' C2' 112.43(16) . . ?
C4' C3' H3'A 109.1 . . ?
C2' C3' H3'A 109.1 . . ?
C4' C3' H3'B 109.1 . . ?
C2' C3' H3'B 109.1 . . ?
H3'A C3' H3'B 107.8 . . ?
C3' C4' S5' 114.70(14) . . ?
C3' C4' H4'A 108.6 . . ?
S5' C4' H4'A 108.6 . . ?
C3' C4' H4'B 108.6 . . ?
S5' C4' H4'B 108.6 . . ?
H4'A C4' H4'B 107.6 . . ?
C4' S5' C6' 101.43(9) . . ?
C11' C6' C7' 111.25(15) . . ?
C11' C6' S1' 111.92(12) . . ?
C7' C6' S1' 104.24(12) . . ?
C11' C6' S5' 111.40(13) . . ?
C7' C6' S5' 106.87(12) . . ?
S1' C6' S5' 110.83(10) . . ?
C8' C7' C6' 113.04(15) . . ?
C8' C7' H7'A 109.0 . . ?
C6' C7' H7'A 109.0 . . ?
C8' C7' H7'B 109.0 . . ?
C6' C7' H7'B 109.0 . . ?
H7'A C7' H7'B 107.8 . . ?
C5 C8' C7' 112.97(15) . . ?
C5 C8' C9' 111.97(15) . . ?
C7' C8' C9' 110.06(16) . . ?
C5 C8' H8' 107.2 . . ?
C7' C8' H8' 107.2 . . ?
C9' C8' H8' 107.2 . . ?
C10' C9' C8' 110.11(15) . . ?
C10' C9' H9'A 109.6 . . ?
C8' C9' H9'A 109.6 . . ?
C10' C9' H9'B 109.6 . . ?
C8' C9' H9'B 109.6 . . ?
H9'A C9' H9'B 108.2 . . ?
C9' C10' C11' 110.77(16) . . ?
C9' C10' H10B 109.5 . . ?
C11' C10' H10B 109.5 . . ?
C9' C10' H10A 109.5 . . ?
C11' C10' H10A 109.5 . . ?
H10B C10' H10A 108.1 . . ?
C6' C11' C10' 112.87(15) . . ?
C6' C11' H11A 109.0 . . ?
C10' C11' H11A 109.0 . . ?
C6' C11' H11B 109.0 . . ?
C10' C11' H11B 109.0 . . ?
H11A C11' H11B 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
C5 O1 C2 O6 177.38(18) . . . . ?
C5 O1 C2 C3 -1.62(19) . . . . ?
O6 C2 C3 C4 -177.9(2) . . . . ?
O1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 O1 C5 C4 1.57(18) . . . . ?
C2 O1 C5 C8' 126.80(16) . . . . ?
C3 C4 C5 O1 -1.0(2) . . . . ?
C3 C4 C5 C8' -123.08(19) . . . . ?
C6' S1' C2' C3' 57.45(16) . . . . ?
S1' C2' C3' C4' -64.7(2) . . . . ?
C2' C3' C4' S5' 67.2(2) . . . . ?
C3' C4' S5' C6' -60.46(16) . . . . ?
C2' S1' C6' C11' 69.83(14) . . . . ?
C2' S1' C6' C7' -169.82(12) . . . . ?
C2' S1' C6' S5' -55.19(11) . . . . ?
C4' S5' C6' C11' -69.80(14) . . . . ?
C4' S5' C6' C7' 168.49(13) . . . . ?
C4' S5' C6' S1' 55.51(11) . . . . ?
C11' C6' C7' C8' -50.3(2) . . . . ?
S1' C6' C7' C8' -171.05(13) . . . . ?
S5' C6' C7' C8' 71.54(17) . . . . ?
O1 C5 C8' C7' -62.9(2) . . . . ?
C4 C5 C8' C7' 55.2(2) . . . . ?
O1 C5 C8' C9' 62.1(2) . . . . ?
C4 C5 C8' C9' -179.91(17) . . . . ?
C6' C7' C8' C5 -178.57(15) . . . . ?
C6' C7' C8' C9' 55.5(2) . . . . ?
C5 C8' C9' C10' 173.92(15) . . . . ?
C7' C8' C9' C10' -59.5(2) . . . . ?
C8' C9' C10' C11' 59.3(2) . . . . ?
C7' C6' C11' C10' 49.5(2) . . . . ?
S1' C6' C11' C10' 165.71(13) . . . . ?
S5' C6' C11' C10' -69.58(18) . . . . ?
C9' C10' C11' C6' -54.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041
