# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1441556'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O4 S2'
_chemical_formula_weight         440.52

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'
N N 0.0061 0.0033 '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                   9.621(3)
_cell_length_b                   14.256(5)
_cell_length_c                   8.097(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.224(5)
_cell_angle_gamma                90.00
_cell_volume                     1035.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2128
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9233
_exptl_absorpt_correction_T_max  0.9390
_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_reflns_number            4686
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1813
_reflns_number_gt                1524
_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, 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)+(0.0447P)²+0.1090P] 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         1813
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.90730(17) 0.90506(11) 0.3196(2) 0.0370(4) Uani 1 1 d . . .
C2 C 1.05662(19) 0.92352(13) 0.3527(2) 0.0482(4) Uani 1 1 d . . .
H2 H 1.0836 0.9744 0.2990 0.058 Uiso 1 1 calc R . .
C3 C 1.1657(2) 0.86571(16) 0.4665(3) 0.0612(6) Uani 1 1 d . . .
H3 H 1.2658 0.8776 0.4880 0.073 Uiso 1 1 calc R . .
C4 C 1.1262(2) 0.79125(15) 0.5471(3) 0.0653(6) Uani 1 1 d . . .
H4 H 1.1996 0.7536 0.6253 0.078 Uiso 1 1 calc R . .
C5 C 0.9786(2) 0.77218(14) 0.5128(3) 0.0643(6) Uani 1 1 d . . .
H5 H 0.9524 0.7211 0.5669 0.077 Uiso 1 1 calc R . .
C6 C 0.86880(19) 0.82824(12) 0.3987(2) 0.0477(4) Uani 1 1 d . . .
H6 H 0.7689 0.8145 0.3748 0.057 Uiso 1 1 calc R . .
C7 C 0.78976(16) 0.96679(10) 0.20280(19) 0.0343(3) Uani 1 1 d . . .
C8 C 0.64967(17) 1.09417(11) -0.0085(2) 0.0409(4) Uani 1 1 d . . .
H8A H 0.6599 1.1571 0.0399 0.049 Uiso 1 1 calc R . .
H8B H 0.6004 1.0978 -0.1362 0.049 Uiso 1 1 calc R . .
C9 C 0.55915(16) 1.03163(10) 0.0730(2) 0.0343(3) Uani 1 1 d . . .
C10 C 0.47443(17) 1.09608(11) 0.1564(2) 0.0384(4) Uani 1 1 d . . .
C11 C 0.3718(2) 1.11410(14) 0.3778(3) 0.0583(5) Uani 1 1 d . . .
H11A H 0.4213 1.1732 0.4139 0.087 Uiso 1 1 calc R . .
H11B H 0.3671 1.0817 0.4795 0.087 Uiso 1 1 calc R . .
H11C H 0.2725 1.1247 0.2947 0.087 Uiso 1 1 calc R . .
N1 N 0.65880(14) 0.96915(8) 0.20642(16) 0.0351(3) Uani 1 1 d . . .
O1 O 0.45398(13) 1.05771(8) 0.29480(14) 0.0430(3) Uani 1 1 d . . .
O2 O 0.43356(17) 1.17306(9) 0.10266(17) 0.0649(4) Uani 1 1 d . . .
S1 S 0.82952(5) 1.03925(3) 0.04871(6) 0.04821(17) 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
C1 C6 1.385(2) . ?
C1 C2 1.388(2) . ?
C1 C7 1.474(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.2712(19) . ?
C7 S1 1.7653(16) . ?
C8 C9 1.551(2) . ?
C8 S1 1.8003(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.4595(19) . ?
C9 C10 1.537(2) . ?
C9 C9 1.591(3) 3_675 ?
C10 O2 1.1935(19) . ?
C10 O1 1.3243(19) . ?
C11 O1 1.4519(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C6 C1 C2 119.46(15) . . ?
C6 C1 C7 119.81(14) . . ?
C2 C1 C7 120.73(15) . . ?
C1 C2 C3 119.77(18) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.17(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.16(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.00(17) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 122.52(14) . . ?
N1 C7 S1 118.10(12) . . ?
C1 C7 S1 119.37(11) . . ?
C9 C8 S1 106.02(10) . . ?
C9 C8 H8A 110.5 . . ?
S1 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
S1 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N1 C9 C10 110.50(12) . . ?
N1 C9 C8 110.27(12) . . ?
C10 C9 C8 108.19(12) . . ?
N1 C9 C9 107.79(14) . 3_675 ?
C10 C9 C9 108.34(15) . 3_675 ?
C8 C9 C9 111.75(15) . 3_675 ?
O2 C10 O1 123.91(15) . . ?
O2 C10 C9 123.14(14) . . ?
O1 C10 C9 112.94(13) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 N1 C9 112.95(12) . . ?
C10 O1 C11 115.83(13) . . ?
C7 S1 C8 90.13(7) . . ?

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
C6 C1 C2 C3 -0.9(2) . . . . ?
C7 C1 C2 C3 178.48(15) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
C7 C1 C6 C5 -177.75(16) . . . . ?
C6 C1 C7 N1 19.4(2) . . . . ?
C2 C1 C7 N1 -159.97(15) . . . . ?
C6 C1 C7 S1 -159.53(12) . . . . ?
C2 C1 C7 S1 21.1(2) . . . . ?
S1 C8 C9 N1 16.61(15) . . . . ?
S1 C8 C9 C10 137.55(11) . . . . ?
S1 C8 C9 C9 -103.26(15) . . . 3_675 ?
N1 C9 C10 O2 150.26(16) . . . . ?
C8 C9 C10 O2 29.5(2) . . . . ?
C9 C9 C10 O2 -91.9(2) 3_675 . . . ?
N1 C9 C10 O1 -28.76(17) . . . . ?
C8 C9 C10 O1 -149.56(13) . . . . ?
C9 C9 C10 O1 89.12(17) 3_675 . . . ?
C1 C7 N1 C9 -176.94(13) . . . . ?
S1 C7 N1 C9 1.99(17) . . . . ?
C10 C9 N1 C7 -131.98(14) . . . . ?
C8 C9 N1 C7 -12.43(18) . . . . ?
C9 C9 N1 C7 109.81(16) 3_675 . . . ?
O2 C10 O1 C11 2.3(2) . . . . ?
C9 C10 O1 C11 -178.73(14) . . . . ?
N1 C7 S1 C8 7.34(13) . . . . ?
C1 C7 S1 C8 -173.70(12) . . . . ?
C9 C8 S1 C7 -12.96(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_20150908laj1_0m
_database_code_depnum_ccdc_archive 'CCDC 1444167'
_audit_update_record             
;
2015-12-27 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O4 S2'
_chemical_formula_weight         440.52

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'
N N 0.0061 0.0033 '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                   11.3995(11)
_cell_length_b                   15.4075(15)
_cell_length_c                   12.3398(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.817(2)
_cell_angle_gamma                90.00
_cell_volume                     2147.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5213
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9259
_exptl_absorpt_correction_T_max  0.9411
_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_reflns_number            11697
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3796
_reflns_number_gt                3191
_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, 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)+(0.0527P)²+0.6859P] 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     SHELXL
_refine_ls_extinction_coef       0.190(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3796
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.024
_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 0.15349(18) 0.04827(13) 0.36903(16) 0.0502(5) Uani 1 1 d . . .
H1 H 0.1774 0.0984 0.3362 0.060 Uiso 1 1 calc R . .
C2 C 0.0936(2) -0.01547(14) 0.30572(17) 0.0600(5) Uani 1 1 d . . .
H2 H 0.0771 -0.0084 0.2303 0.072 Uiso 1 1 calc R . .
C3 C 0.05809(19) -0.08996(13) 0.3543(2) 0.0600(6) Uani 1 1 d . . .
H3 H 0.0164 -0.1325 0.3117 0.072 Uiso 1 1 calc R . .
C4 C 0.08413(18) -0.10143(13) 0.4654(2) 0.0570(5) Uani 1 1 d . . .
H4 H 0.0614 -0.1523 0.4974 0.068 Uiso 1 1 calc R . .
C5 C 0.14407(16) -0.03766(12) 0.52992(17) 0.0480(5) Uani 1 1 d . . .
H5 H 0.1613 -0.0455 0.6051 0.058 Uiso 1 1 calc R . .
C6 C 0.17829(15) 0.03805(11) 0.48173(15) 0.0406(4) Uani 1 1 d . . .
C7 C 0.23915(15) 0.10881(11) 0.54727(14) 0.0396(4) Uani 1 1 d . . .
C8 C 0.32709(15) 0.24151(12) 0.58287(13) 0.0394(4) Uani 1 1 d . . .
C9 C 0.34851(17) 0.20059(13) 0.69942(15) 0.0474(5) Uani 1 1 d . . .
H9A H 0.3053 0.2325 0.7491 0.057 Uiso 1 1 calc R . .
H9B H 0.4321 0.2019 0.7279 0.057 Uiso 1 1 calc R . .
C10 C 0.44202(16) 0.24917(14) 0.53105(16) 0.0480(5) Uani 1 1 d . . .
C11 C 0.6063(2) 0.1675(2) 0.4912(3) 0.1009(11) Uani 1 1 d . . .
H11A H 0.5812 0.1734 0.4140 0.151 Uiso 1 1 calc R . .
H11B H 0.6409 0.1112 0.5060 0.151 Uiso 1 1 calc R . .
H11C H 0.6640 0.2115 0.5147 0.151 Uiso 1 1 calc R . .
C12 C -0.05927(17) 0.30399(13) 0.72534(17) 0.0493(5) Uani 1 1 d . . .
H12 H 0.0080 0.2809 0.7663 0.059 Uiso 1 1 calc R . .
C13 C -0.16763(19) 0.29862(15) 0.7642(2) 0.0640(6) Uani 1 1 d . . .
H13 H -0.1733 0.2706 0.8301 0.077 Uiso 1 1 calc R . .
C14 C -0.26682(19) 0.33479(17) 0.7052(2) 0.0745(7) Uani 1 1 d . . .
H14 H -0.3395 0.3311 0.7311 0.089 Uiso 1 1 calc R . .
C15 C -0.25844(19) 0.37609(17) 0.6085(3) 0.0771(8) Uani 1 1 d . . .
H15 H -0.3253 0.4017 0.5699 0.092 Uiso 1 1 calc R . .
C16 C -0.15145(17) 0.38025(14) 0.5673(2) 0.0605(6) Uani 1 1 d . . .
H16 H -0.1469 0.4074 0.5007 0.073 Uiso 1 1 calc R . .
C17 C -0.05062(15) 0.34345(11) 0.62629(16) 0.0438(4) Uani 1 1 d . . .
C18 C 0.06467(15) 0.34648(11) 0.58357(14) 0.0385(4) Uani 1 1 d . . .
C19 C 0.22606(17) 0.36457(13) 0.46312(15) 0.0458(4) Uani 1 1 d . . .
H19A H 0.2432 0.3214 0.4103 0.055 Uiso 1 1 calc R . .
H19B H 0.2681 0.4175 0.4504 0.055 Uiso 1 1 calc R . .
C20 C 0.26474(14) 0.33118(12) 0.58154(13) 0.0382(4) Uani 1 1 d . . .
C21 C 0.34779(16) 0.39589(13) 0.64923(16) 0.0462(4) Uani 1 1 d . . .
C22 C 0.3788(3) 0.54311(18) 0.6984(3) 0.0927(9) Uani 1 1 d . . .
H22A H 0.3880 0.5280 0.7746 0.139 Uiso 1 1 calc R . .
H22B H 0.3391 0.5980 0.6878 0.139 Uiso 1 1 calc R . .
H22C H 0.4554 0.5471 0.6745 0.139 Uiso 1 1 calc R . .
N1 N 0.25372(12) 0.18347(9) 0.50753(11) 0.0395(3) Uani 1 1 d . . .
N2 N 0.16110(12) 0.32232(10) 0.63949(11) 0.0397(3) Uani 1 1 d . . .
O1 O 0.46797(13) 0.30863(11) 0.47744(14) 0.0684(4) Uani 1 1 d . . .
O2 O 0.50540(13) 0.17737(11) 0.54957(15) 0.0733(5) Uani 1 1 d . . .
O3 O 0.43444(14) 0.37581(11) 0.70941(15) 0.0746(5) Uani 1 1 d . . .
O4 O 0.30898(13) 0.47658(9) 0.63505(13) 0.0656(4) Uani 1 1 d . . .
S1 S 0.29637(5) 0.09016(4) 0.68562(4) 0.0585(2) Uani 1 1 d . . .
S2 S 0.06977(5) 0.38466(4) 0.45014(4) 0.0612(2) 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
C1 C2 1.377(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.474(3) . ?
C7 N1 1.270(2) . ?
C7 S1 1.7663(18) . ?
C8 N1 1.467(2) . ?
C8 C10 1.539(2) . ?
C8 C20 1.553(2) . ?
C8 C9 1.559(2) . ?
C9 S1 1.803(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.191(2) . ?
C10 O2 1.324(2) . ?
C11 O2 1.446(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.381(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.482(2) . ?
C18 N2 1.272(2) . ?
C18 S2 1.7568(19) . ?
C19 C20 1.555(2) . ?
C19 S2 1.794(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N2 1.468(2) . ?
C20 C21 1.540(2) . ?
C21 O3 1.193(2) . ?
C21 O4 1.323(2) . ?
C22 O4 1.458(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C2 C1 C6 120.30(19) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.34(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.67(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.52(18) . . ?
C5 C6 C7 121.67(17) . . ?
C1 C6 C7 118.80(16) . . ?
N1 C7 C6 122.32(16) . . ?
N1 C7 S1 118.03(14) . . ?
C6 C7 S1 119.64(13) . . ?
N1 C8 C10 103.16(13) . . ?
N1 C8 C20 108.36(13) . . ?
C10 C8 C20 109.99(15) . . ?
N1 C8 C9 110.02(15) . . ?
C10 C8 C9 112.27(14) . . ?
C20 C8 C9 112.56(14) . . ?
C8 C9 S1 106.64(12) . . ?
C8 C9 H9A 110.4 . . ?
S1 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
S1 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
O1 C10 O2 124.59(18) . . ?
O1 C10 C8 125.44(18) . . ?
O2 C10 C8 109.86(17) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.4(2) . . ?
C17 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 119.21(18) . . ?
C12 C17 C18 120.16(16) . . ?
C16 C17 C18 120.63(19) . . ?
N2 C18 C17 122.74(17) . . ?
N2 C18 S2 118.05(13) . . ?
C17 C18 S2 119.21(13) . . ?
C20 C19 S2 106.99(12) . . ?
C20 C19 H19A 110.3 . . ?
S2 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
S2 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
N2 C20 C21 105.79(13) . . ?
N2 C20 C8 108.04(14) . . ?
C21 C20 C8 108.87(14) . . ?
N2 C20 C19 110.14(13) . . ?
C21 C20 C19 111.72(15) . . ?
C8 C20 C19 112.03(14) . . ?
O3 C21 O4 124.02(18) . . ?
O3 C21 C20 124.43(18) . . ?
O4 C21 C20 111.51(15) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C8 113.62(14) . . ?
C18 N2 C20 113.70(14) . . ?
C10 O2 C11 117.0(2) . . ?
C21 O4 C22 116.18(19) . . ?
C7 S1 C9 90.66(8) . . ?
C18 S2 C19 91.01(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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 178.20(16) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C6 C7 -178.06(18) . . . . ?
C5 C6 C7 N1 -168.23(16) . . . . ?
C1 C6 C7 N1 10.9(3) . . . . ?
C5 C6 C7 S1 12.7(2) . . . . ?
C1 C6 C7 S1 -168.16(14) . . . . ?
N1 C8 C9 S1 10.37(17) . . . . ?
C10 C8 C9 S1 -103.90(15) . . . . ?
C20 C8 C9 S1 131.33(13) . . . . ?
N1 C8 C10 O1 100.8(2) . . . . ?
C20 C8 C10 O1 -14.6(3) . . . . ?
C9 C8 C10 O1 -140.8(2) . . . . ?
N1 C8 C10 O2 -75.68(18) . . . . ?
C20 C8 C10 O2 168.90(15) . . . . ?
C9 C8 C10 O2 42.7(2) . . . . ?
C17 C12 C13 C14 -1.7(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C13 C12 C17 C16 2.0(3) . . . . ?
C13 C12 C17 C18 -178.06(17) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C15 C16 C17 C18 179.55(19) . . . . ?
C12 C17 C18 N2 -7.8(3) . . . . ?
C16 C17 C18 N2 172.19(18) . . . . ?
C12 C17 C18 S2 172.06(14) . . . . ?
C16 C17 C18 S2 -8.0(2) . . . . ?
N1 C8 C20 N2 72.41(16) . . . . ?
C10 C8 C20 N2 -175.51(13) . . . . ?
C9 C8 C20 N2 -49.50(18) . . . . ?
N1 C8 C20 C21 -173.15(13) . . . . ?
C10 C8 C20 C21 -61.07(17) . . . . ?
C9 C8 C20 C21 64.94(18) . . . . ?
N1 C8 C20 C19 -49.08(18) . . . . ?
C10 C8 C20 C19 63.00(18) . . . . ?
C9 C8 C20 C19 -170.99(15) . . . . ?
S2 C19 C20 N2 3.48(17) . . . . ?
S2 C19 C20 C21 -113.78(14) . . . . ?
S2 C19 C20 C8 123.75(13) . . . . ?
N2 C20 C21 O3 102.5(2) . . . . ?
C8 C20 C21 O3 -13.4(3) . . . . ?
C19 C20 C21 O3 -137.6(2) . . . . ?
N2 C20 C21 O4 -75.46(19) . . . . ?
C8 C20 C21 O4 168.64(15) . . . . ?
C19 C20 C21 O4 44.4(2) . . . . ?
C6 C7 N1 C8 -173.92(14) . . . . ?
S1 C7 N1 C8 5.20(19) . . . . ?
C10 C8 N1 C7 109.79(16) . . . . ?
C20 C8 N1 C7 -133.63(15) . . . . ?
C9 C8 N1 C7 -10.18(19) . . . . ?
C17 C18 N2 C20 -179.73(15) . . . . ?
S2 C18 N2 C20 0.4(2) . . . . ?
C21 C20 N2 C18 118.29(16) . . . . ?
C8 C20 N2 C18 -125.25(15) . . . . ?
C19 C20 N2 C18 -2.6(2) . . . . ?
O1 C10 O2 C11 -6.6(3) . . . . ?
C8 C10 O2 C11 169.9(2) . . . . ?
O3 C21 O4 C22 0.0(3) . . . . ?
C20 C21 O4 C22 177.93(19) . . . . ?
N1 C7 S1 C9 1.25(15) . . . . ?
C6 C7 S1 C9 -179.60(14) . . . . ?
C8 C9 S1 C7 -6.58(13) . . . . ?
N2 C18 S2 C19 1.55(15) . . . . ?
C17 C18 S2 C19 -178.30(14) . . . . ?
C20 C19 S2 C18 -2.75(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054
