# 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_cd214198
_database_code_depnum_ccdc_archive 'CCDC 996223'
_audit_update_record             
;
2014-04-09 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 N2 O4 S4'
_chemical_formula_weight         662.87

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   28.621(7)
_cell_length_b                   26.533(8)
_cell_length_c                   9.756(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7409(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1793
_cell_measurement_theta_min      4.663
_cell_measurement_theta_max      56.536

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             2784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5525
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.2008
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             6523
_reflns_number_gt                2591
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.967

_reflns_special_details          
; 
 Data were apparently pre-merged, so _diffrn_reflns_number 
 etc. will have to be added later. 
  
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.56(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6523
_refine_ls_number_parameters     401
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2146
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.1994
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.574 17 2 ' '
2 0.250 0.064 0.709 271 80 ' '
3 0.500 0.000 0.074 17 2 ' '
4 0.750 -0.064 0.206 271 82 ' '
5 0.574 0.094 0.208 8 1 ' '
6 0.926 0.094 0.708 8 1 ' '
7 0.750 0.436 0.560 271 82 ' '
8 0.074 0.406 0.208 8 1 ' '
9 0.426 0.406 0.708 8 1 ' '
10 0.000 0.500 0.074 17 2 ' '
11 0.250 0.564 0.183 271 80 ' '
12 0.500 0.500 0.574 17 2 ' '
13 0.574 0.594 0.708 8 1 ' '
14 0.926 0.594 0.208 8 1 ' '
15 0.074 0.906 0.708 8 1 ' '
16 0.426 0.906 0.208 8 1 ' '
_platon_squeeze_details          
;
;


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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15731(14) 0.22731(13) 0.8622(3) 0.0776(10) Uani 1 1 d . . . . .
S2 S 0.03676(11) 0.35722(14) 0.9142(3) 0.0809(11) Uani 1 1 d . . . . .
S3 S 0.09686(16) 0.53234(13) 0.7663(4) 0.0995(14) Uani 1 1 d . . . . .
S4 S 0.16729(11) 0.40294(11) 1.0385(3) 0.0730(10) Uani 1 1 d . . . . .
N1 N 0.0851(3) 0.3932(3) 0.9257(9) 0.063(3) Uani 1 1 d . . . . .
N2 N 0.1504(3) 0.2884(3) 0.8331(10) 0.059(2) Uani 1 1 d . . . . .
O1 O 0.2040(3) 0.2158(3) 0.8238(12) 0.117(4) Uani 1 1 d . . . . .
O2 O 0.1203(4) 0.2037(3) 0.7911(9) 0.103(3) Uani 1 1 d . . . . .
O3 O 0.0474(3) 0.3098(3) 0.9767(8) 0.095(3) Uani 1 1 d . . . . .
O4 O 0.0003(3) 0.3882(4) 0.9658(9) 0.114(4) Uani 1 1 d . . . . .
C1 C 0.0781(4) 0.4432(5) 0.8776(13) 0.069(3) Uani 1 1 d . . . . .
H1 H 0.0516 0.4603 0.9071 0.083 Uiso 1 1 calc R U . . .
C2 C 0.1067(5) 0.4666(4) 0.7944(13) 0.069(4) Uani 1 1 d . . . . .
C3 C 0.1479(5) 0.4436(4) 0.7354(11) 0.075(4) Uani 1 1 d . . . . .
H3A H 0.1755 0.4589 0.7751 0.090 Uiso 1 1 calc R U . . .
H3B H 0.1484 0.4500 0.6376 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1492(4) 0.3874(4) 0.7601(11) 0.062(3) Uani 1 1 d . . . . .
H4A H 0.1304 0.3706 0.6912 0.074 Uiso 1 1 calc R U . . .
H4B H 0.1811 0.3755 0.7506 0.074 Uiso 1 1 calc R U . . .
C5 C 0.1314(3) 0.3735(4) 0.8998(10) 0.047(3) Uani 1 1 d . . . . .
C6 C 0.1359(3) 0.3180(4) 0.9275(11) 0.054(3) Uani 1 1 d . . . . .
H6 H 0.1282 0.3052 1.0133 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1493(5) 0.2146(4) 1.0391(14) 0.061(3) Uani 1 1 d . . . . .
C8 C 0.1891(5) 0.2102(4) 1.1213(14) 0.071(4) Uani 1 1 d . . . . .
H8 H 0.2191 0.2151 1.0869 0.085 Uiso 1 1 calc R U . . .
C9 C 0.1810(6) 0.1982(5) 1.2576(19) 0.098(5) Uani 1 1 d . . . . .
H9 H 0.2066 0.1948 1.3157 0.118 Uiso 1 1 calc R U . . .
C10 C 0.1369(7) 0.1910(5) 1.3113(15) 0.084(4) Uani 1 1 d . . . . .
C11 C 0.1005(5) 0.1981(5) 1.2262(16) 0.076(4) Uani 1 1 d . . . . .
H11 H 0.0705 0.1958 1.2621 0.092 Uiso 1 1 calc R U . . .
C12 C 0.1054(4) 0.2083(4) 1.0910(16) 0.068(4) Uani 1 1 d . . . . .
H12 H 0.0793 0.2109 1.0345 0.081 Uiso 1 1 calc R U . . .
C13 C 0.1321(7) 0.1769(6) 1.4592(17) 0.140(6) Uani 1 1 d . . . . .
H13A H 0.1002 0.1813 1.4873 0.209 Uiso 1 1 calc R U . . .
H13B H 0.1520 0.1980 1.5137 0.209 Uiso 1 1 calc R U . . .
H13C H 0.1410 0.1423 1.4713 0.209 Uiso 1 1 calc R U . . .
C14 C 0.0278(4) 0.3456(5) 0.7408(11) 0.061(3) Uani 1 1 d . . . . .
C15 C 0.0411(4) 0.3023(5) 0.6770(16) 0.076(4) Uani 1 1 d . . . . .
H15 H 0.0561 0.2767 0.7250 0.092 Uiso 1 1 calc R U . . .
C16 C 0.0318(4) 0.2975(5) 0.5414(18) 0.080(4) Uani 1 1 d . . . . .
H16 H 0.0392 0.2671 0.4992 0.097 Uiso 1 1 calc R U . . .
C17 C 0.0128(4) 0.3332(6) 0.4655(15) 0.073(4) Uani 1 1 d . . . . .
C18 C 0.0001(4) 0.3774(5) 0.5251(15) 0.073(3) Uani 1 1 d . . . . .
H18 H -0.0132 0.4027 0.4717 0.087 Uiso 1 1 calc R U . . .
C19 C 0.0066(4) 0.3856(5) 0.6646(15) 0.070(3) Uani 1 1 d . . . . .
H19 H -0.0023 0.4156 0.7063 0.084 Uiso 1 1 calc R U . . .
C20 C 0.0049(5) 0.3262(5) 0.3134(16) 0.108(5) Uani 1 1 d . . . . .
H20A H 0.0115 0.3572 0.2665 0.162 Uiso 1 1 calc R U . . .
H20B H -0.0270 0.3166 0.2975 0.162 Uiso 1 1 calc R U . . .
H20C H 0.0253 0.3002 0.2798 0.162 Uiso 1 1 calc R U . . .
C21 C 0.0951(5) 0.5334(5) 0.5864(13) 0.075(4) Uani 1 1 d . . . . .
C22 C 0.0720(5) 0.4985(5) 0.5088(15) 0.095(5) Uani 1 1 d . . . . .
H22 H 0.0577 0.4714 0.5525 0.114 Uiso 1 1 calc R U . . .
C23 C 0.0691(6) 0.5020(5) 0.3700(16) 0.105(5) Uani 1 1 d . . . . .
H23 H 0.0524 0.4779 0.3211 0.126 Uiso 1 1 calc R U . . .
C24 C 0.0907(5) 0.5408(6) 0.3012(13) 0.082(4) Uani 1 1 d . . . . .
C25 C 0.1139(6) 0.5761(5) 0.381(2) 0.105(5) Uani 1 1 d . . . . .
H25 H 0.1277 0.6038 0.3387 0.126 Uiso 1 1 calc R U . . .
C26 C 0.1172(5) 0.5716(6) 0.5198(19) 0.096(4) Uani 1 1 d . . . . .
H26 H 0.1347 0.5948 0.5694 0.115 Uiso 1 1 calc R U . . .
C27 C 0.0903(8) 0.5451(6) 0.1506(17) 0.152(8) Uani 1 1 d . . . . .
H27A H 0.1061 0.5754 0.1236 0.228 Uiso 1 1 calc R U . . .
H27B H 0.0585 0.5462 0.1187 0.228 Uiso 1 1 calc R U . . .
H27C H 0.1058 0.5165 0.1112 0.228 Uiso 1 1 calc R U . . .
C28 C 0.2248(4) 0.3843(5) 0.9939(11) 0.062(3) Uani 1 1 d . . . . .
C29 C 0.2531(5) 0.4162(5) 0.9300(14) 0.085(4) Uani 1 1 d . . . . .
H29 H 0.2422 0.4482 0.9083 0.102 Uiso 1 1 calc R U . . .
C30 C 0.2992(6) 0.4027(8) 0.8938(14) 0.107(5) Uani 1 1 d . . . . .
H30 H 0.3187 0.4249 0.8475 0.129 Uiso 1 1 calc R U . . .
C31 C 0.3141(5) 0.3551(9) 0.9301(17) 0.096(5) Uani 1 1 d . . . . .
C32 C 0.2857(7) 0.3225(6) 0.9981(18) 0.108(6) Uani 1 1 d . . . . .
H32 H 0.2964 0.2906 1.0222 0.129 Uiso 1 1 calc R U . . .
C33 C 0.2404(5) 0.3375(5) 1.0313(16) 0.092(4) Uani 1 1 d . . . . .
H33 H 0.2208 0.3157 1.0788 0.111 Uiso 1 1 calc R U . . .
C34 C 0.3647(6) 0.3400(9) 0.884(2) 0.182(9) Uani 1 1 d . . . . .
H34A H 0.3746 0.3107 0.9337 0.273 Uiso 1 1 calc R U . . .
H34B H 0.3857 0.3674 0.9019 0.273 Uiso 1 1 calc R U . . .
H34C H 0.3647 0.3327 0.7875 0.273 Uiso 1 1 calc R U . . .


_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 1.413(9) . ?
S1 O1 1.422(9) . ?
S1 N2 1.658(9) . ?
S1 C7 1.773(14) . ?
S2 O4 1.419(8) . ?
S2 O3 1.432(8) . ?
S2 N1 1.685(10) . ?
S2 C14 1.739(12) . ?
S3 C21 1.756(13) . ?
S3 C2 1.787(12) . ?
S4 C28 1.774(13) . ?
S4 C5 1.871(10) . ?
N1 C1 1.419(14) . ?
N1 C5 1.447(12) . ?
N2 C6 1.280(12) . ?
C1 C2 1.309(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.448(15) . ?
C3 C4 1.511(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.500(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.502(13) . ?
C6 H6 0.9300 . ?
C7 C12 1.366(15) . ?
C7 C8 1.398(16) . ?
C8 C9 1.39(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.346(18) . ?
C10 C13 1.497(19) . ?
C11 C12 1.354(16) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.363(15) . ?
C14 C19 1.430(15) . ?
C15 C16 1.355(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.319(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(16) . ?
C17 C20 1.512(18) . ?
C18 C19 1.391(17) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.358(18) . ?
C21 C22 1.367(17) . ?
C22 C23 1.360(18) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(18) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(18) . ?
C24 C27 1.47(2) . ?
C25 C26 1.36(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.325(16) . ?
C28 C33 1.370(15) . ?
C29 C30 1.413(18) . ?
C29 H29 0.9300 . ?
C30 C31 1.38(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.36(2) . ?
C31 C34 1.57(2) . ?
C32 C33 1.39(2) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
O2 S1 O1 118.7(6) . . ?
O2 S1 N2 105.0(6) . . ?
O1 S1 N2 106.1(5) . . ?
O2 S1 C7 107.3(6) . . ?
O1 S1 C7 109.7(7) . . ?
N2 S1 C7 109.7(5) . . ?
O4 S2 O3 120.9(6) . . ?
O4 S2 N1 104.5(6) . . ?
O3 S2 N1 107.2(5) . . ?
O4 S2 C14 109.8(6) . . ?
O3 S2 C14 106.9(6) . . ?
N1 S2 C14 106.7(5) . . ?
C21 S3 C2 100.0(6) . . ?
C28 S4 C5 102.5(5) . . ?
C1 N1 C5 114.1(9) . . ?
C1 N1 S2 113.1(8) . . ?
C5 N1 S2 122.3(7) . . ?
C6 N2 S1 121.1(8) . . ?
C2 C1 N1 124.1(11) . . ?
C2 C1 H1 117.9 . . ?
N1 C1 H1 117.9 . . ?
C1 C2 C3 123.6(11) . . ?
C1 C2 S3 117.5(10) . . ?
C3 C2 S3 118.6(11) . . ?
C2 C3 C4 112.0(11) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 112.2(9) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C4 112.4(8) . . ?
N1 C5 C6 113.7(8) . . ?
C4 C5 C6 112.0(9) . . ?
N1 C5 S4 103.0(7) . . ?
C4 C5 S4 111.6(7) . . ?
C6 C5 S4 103.3(6) . . ?
N2 C6 C5 120.0(10) . . ?
N2 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C7 C8 121.8(13) . . ?
C12 C7 S1 120.2(11) . . ?
C8 C7 S1 118.0(11) . . ?
C9 C8 C7 115.6(13) . . ?
C9 C8 H8 122.2 . . ?
C7 C8 H8 122.2 . . ?
C10 C9 C8 123.3(14) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C11 C10 C9 117.1(14) . . ?
C11 C10 C13 123.9(17) . . ?
C9 C10 C13 119.0(17) . . ?
C10 C11 C12 123.3(14) . . ?
C10 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C7 118.7(13) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.5(12) . . ?
C15 C14 S2 123.6(10) . . ?
C19 C14 S2 115.9(11) . . ?
C16 C15 C14 118.0(12) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C17 C16 C15 124.2(14) . . ?
C17 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
C16 C17 C18 119.3(14) . . ?
C16 C17 C20 121.6(15) . . ?
C18 C17 C20 119.1(15) . . ?
C17 C18 C19 121.2(13) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C14 116.7(12) . . ?
C18 C19 H19 121.6 . . ?
C14 C19 H19 121.6 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 117.7(13) . . ?
C26 C21 S3 118.5(13) . . ?
C22 C21 S3 123.8(12) . . ?
C23 C22 C21 122.3(14) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 120.7(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 116.5(12) . . ?
C23 C24 C27 122.7(16) . . ?
C25 C24 C27 120.8(16) . . ?
C26 C25 C24 122.1(14) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C21 C26 C25 120.7(15) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
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 . . ?
C29 C28 C33 120.3(13) . . ?
C29 C28 S4 120.2(11) . . ?
C33 C28 S4 119.4(11) . . ?
C28 C29 C30 121.7(13) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 117.2(15) . . ?
C31 C30 H30 121.4 . . ?
C29 C30 H30 121.4 . . ?
C32 C31 C30 121.5(16) . . ?
C32 C31 C34 122(2) . . ?
C30 C31 C34 116(2) . . ?
C31 C32 C33 119.2(16) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C28 C33 C32 120.0(15) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
O4 S2 N1 C1 -45.5(9) . . . . ?
O3 S2 N1 C1 -175.0(8) . . . . ?
C14 S2 N1 C1 70.8(9) . . . . ?
O4 S2 N1 C5 171.8(8) . . . . ?
O3 S2 N1 C5 42.3(9) . . . . ?
C14 S2 N1 C5 -71.9(9) . . . . ?
O2 S1 N2 C6 107.5(9) . . . . ?
O1 S1 N2 C6 -126.0(9) . . . . ?
C7 S1 N2 C6 -7.5(10) . . . . ?
C5 N1 C1 C2 12.8(16) . . . . ?
S2 N1 C1 C2 -133.1(11) . . . . ?
N1 C1 C2 C3 3.2(19) . . . . ?
N1 C1 C2 S3 -170.6(8) . . . . ?
C21 S3 C2 C1 -127.3(11) . . . . ?
C21 S3 C2 C3 58.6(11) . . . . ?
C1 C2 C3 C4 10.3(16) . . . . ?
S3 C2 C3 C4 -176.0(8) . . . . ?
C2 C3 C4 C5 -38.1(13) . . . . ?
C1 N1 C5 C4 -41.0(12) . . . . ?
S2 N1 C5 C4 101.4(10) . . . . ?
C1 N1 C5 C6 -169.6(9) . . . . ?
S2 N1 C5 C6 -27.2(12) . . . . ?
C1 N1 C5 S4 79.3(9) . . . . ?
S2 N1 C5 S4 -138.4(6) . . . . ?
C3 C4 C5 N1 54.5(12) . . . . ?
C3 C4 C5 C6 -176.0(9) . . . . ?
C3 C4 C5 S4 -60.7(11) . . . . ?
C28 S4 C5 N1 -173.6(7) . . . . ?
C28 S4 C5 C4 -52.7(8) . . . . ?
C28 S4 C5 C6 67.8(8) . . . . ?
S1 N2 C6 C5 178.1(7) . . . . ?
N1 C5 C6 N2 124.0(10) . . . . ?
C4 C5 C6 N2 -4.8(13) . . . . ?
S4 C5 C6 N2 -125.1(8) . . . . ?
O2 S1 C7 C12 -30.3(11) . . . . ?
O1 S1 C7 C12 -160.6(9) . . . . ?
N2 S1 C7 C12 83.2(10) . . . . ?
O2 S1 C7 C8 148.3(9) . . . . ?
O1 S1 C7 C8 18.0(10) . . . . ?
N2 S1 C7 C8 -98.2(9) . . . . ?
C12 C7 C8 C9 1.2(17) . . . . ?
S1 C7 C8 C9 -177.4(9) . . . . ?
C7 C8 C9 C10 -0.3(19) . . . . ?
C8 C9 C10 C11 -3(2) . . . . ?
C8 C9 C10 C13 178.6(14) . . . . ?
C9 C10 C11 C12 4.7(19) . . . . ?
C13 C10 C11 C12 -176.5(14) . . . . ?
C10 C11 C12 C7 -3.9(19) . . . . ?
C8 C7 C12 C11 0.7(17) . . . . ?
S1 C7 C12 C11 179.3(9) . . . . ?
O4 S2 C14 C15 -148.5(10) . . . . ?
O3 S2 C14 C15 -15.6(11) . . . . ?
N1 S2 C14 C15 98.8(11) . . . . ?
O4 S2 C14 C19 33.7(11) . . . . ?
O3 S2 C14 C19 166.6(8) . . . . ?
N1 S2 C14 C19 -79.0(9) . . . . ?
C19 C14 C15 C16 -2.9(18) . . . . ?
S2 C14 C15 C16 179.5(9) . . . . ?
C14 C15 C16 C17 4(2) . . . . ?
C15 C16 C17 C18 -2.1(19) . . . . ?
C15 C16 C17 C20 177.7(12) . . . . ?
C16 C17 C18 C19 -0.2(18) . . . . ?
C20 C17 C18 C19 179.9(11) . . . . ?
C17 C18 C19 C14 0.8(16) . . . . ?
C15 C14 C19 C18 0.8(16) . . . . ?
S2 C14 C19 C18 178.6(8) . . . . ?
C2 S3 C21 C26 -138.0(11) . . . . ?
C2 S3 C21 C22 43.1(13) . . . . ?
C26 C21 C22 C23 -3(2) . . . . ?
S3 C21 C22 C23 176.3(13) . . . . ?
C21 C22 C23 C24 2(3) . . . . ?
C22 C23 C24 C25 -2(2) . . . . ?
C22 C23 C24 C27 177.5(16) . . . . ?
C23 C24 C25 C26 3(2) . . . . ?
C27 C24 C25 C26 -176.2(15) . . . . ?
C22 C21 C26 C25 4(2) . . . . ?
S3 C21 C26 C25 -175.2(12) . . . . ?
C24 C25 C26 C21 -4(2) . . . . ?
C5 S4 C28 C29 100.4(10) . . . . ?
C5 S4 C28 C33 -82.4(10) . . . . ?
C33 C28 C29 C30 2.3(19) . . . . ?
S4 C28 C29 C30 179.5(10) . . . . ?
C28 C29 C30 C31 -1(2) . . . . ?
C29 C30 C31 C32 0(2) . . . . ?
C29 C30 C31 C34 177.6(13) . . . . ?
C30 C31 C32 C33 0(2) . . . . ?
C34 C31 C32 C33 -177.3(14) . . . . ?
C29 C28 C33 C32 -2.1(19) . . . . ?
S4 C28 C33 C32 -179.3(10) . . . . ?
C31 C32 C33 C28 1(2) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.080

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd214392
_database_code_depnum_ccdc_archive 'CCDC 1013188'
_audit_update_record             
;
2014-07-10 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H38 N2 O4 S4'
_chemical_formula_weight         690.92

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5970(13)
_cell_length_b                   13.9714(19)
_cell_length_c                   14.765(2)
_cell_angle_alpha                105.066(3)
_cell_angle_beta                 107.053(3)
_cell_angle_gamma                97.126(3)
_cell_volume                     1784.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4175
_cell_measurement_theta_min      4.914
_cell_measurement_theta_max      53.764

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.307
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10140
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.519
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6514
_reflns_number_gt                5329
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1149P)²+0.0712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6514
_refine_ls_number_parameters     425
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.59310(6) 0.13531(5) 0.13618(5) 0.0455(2) Uani 1 1 d . . . . .
S2 S 0.11358(7) -0.01973(4) 0.10590(4) 0.0453(2) Uani 1 1 d . . . . .
S3 S 0.33564(7) 0.27970(5) 0.41324(4) 0.0473(2) Uani 1 1 d . . . . .
S4 S 0.19136(9) 0.46212(5) 0.13998(6) 0.0575(2) Uani 1 1 d . . . . .
N1 N 0.4125(2) 0.09813(16) 0.10662(16) 0.0470(5) Uani 1 1 d D . . . .
N2 N 0.2308(2) 0.26943(14) 0.29972(14) 0.0429(5) Uani 1 1 d . . . . .
O1 O 0.6251(2) 0.09578(14) 0.04705(14) 0.0553(5) Uani 1 1 d . . . . .
O2 O 0.6287(2) 0.24167(14) 0.18475(15) 0.0577(5) Uani 1 1 d . . . . .
O3 O 0.4785(2) 0.34009(16) 0.43226(14) 0.0645(5) Uani 1 1 d . . . . .
O4 O 0.3229(2) 0.17981(14) 0.42002(14) 0.0616(5) Uani 1 1 d . . . . .
C1 C 0.3376(3) 0.14684(18) 0.16633(17) 0.0412(5) Uani 1 1 d . . . . .
H1 H 0.3823 0.2136 0.2057 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2084(2) 0.10750(16) 0.17286(16) 0.0369(5) Uani 1 1 d . . . . .
C3 C 0.1294(2) 0.17159(16) 0.23212(17) 0.0394(5) Uani 1 1 d . . . . .
H3 H 0.0969 0.1342 0.2727 0.047 Uiso 1 1 calc R U . . .
C4 C -0.0076(2) 0.19539(18) 0.16500(18) 0.0429(5) Uani 1 1 d . . . . .
H4A H -0.0740 0.1321 0.1193 0.051 Uiso 1 1 calc R U . . .
H4B H -0.0607 0.2293 0.2060 0.051 Uiso 1 1 calc R U . . .
C5 C 0.0305(3) 0.26196(17) 0.10519(17) 0.0422(5) Uani 1 1 d . . . . .
H5 H 0.0677 0.2221 0.0558 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1554(3) 0.35184(17) 0.17470(18) 0.0424(5) Uani 1 1 d . . . . .
C7 C 0.2429(3) 0.35212(17) 0.26334(17) 0.0423(5) Uani 1 1 d . . . . .
H7 H 0.3159 0.4102 0.3032 0.051 Uiso 1 1 calc R U . . .
C8 C -0.1086(3) 0.2928(2) 0.0492(2) 0.0584(7) Uani 1 1 d . . . . .
H8A H -0.1404 0.3384 0.0960 0.088 Uiso 1 1 calc R U . . .
H8B H -0.1869 0.2334 0.0120 0.088 Uiso 1 1 calc R U . . .
H8C H -0.0858 0.3259 0.0042 0.088 Uiso 1 1 calc R U . . .
C9 C 0.6733(3) 0.0751(2) 0.2222(2) 0.0556(7) Uani 1 1 d . . . . .
C10 C 0.7112(4) -0.0175(3) 0.1882(3) 0.0774(9) Uani 1 1 d . . . . .
H10 H 0.7008 -0.0450 0.1215 0.093 Uiso 1 1 calc R U . . .
C11 C 0.7639(5) -0.0668(4) 0.2555(4) 0.1006(13) Uani 1 1 d . . . . .
H11 H 0.7919 -0.1277 0.2338 0.121 Uiso 1 1 calc R U . . .
C12 C 0.7772(5) -0.0298(4) 0.3540(4) 0.1042(15) Uani 1 1 d . . . . .
C13 C 0.7421(5) 0.0620(4) 0.3859(3) 0.1041(14) Uani 1 1 d . . . . .
H13 H 0.7538 0.0890 0.4529 0.125 Uiso 1 1 calc R U . . .
C14 C 0.6891(4) 0.1167(3) 0.3210(2) 0.0771(9) Uani 1 1 d . . . . .
H14 H 0.6654 0.1791 0.3437 0.093 Uiso 1 1 calc R U . . .
C15 C 0.8265(6) -0.0907(5) 0.4250(5) 0.161(3) Uani 1 1 d . . . . .
H15A H 0.7457 -0.1459 0.4122 0.242 Uiso 1 1 calc R U . . .
H15B H 0.8544 -0.0475 0.4926 0.242 Uiso 1 1 calc R U . . .
H15C H 0.9105 -0.1171 0.4151 0.242 Uiso 1 1 calc R U . . .
C16 C 0.1726(3) -0.08392(17) 0.19508(17) 0.0432(5) Uani 1 1 d . . . . .
C17 C 0.3103(3) -0.0535(2) 0.2701(2) 0.0643(8) Uani 1 1 d . . . . .
H17 H 0.3734 0.0075 0.2807 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3537(4) -0.1137(2) 0.3291(2) 0.0716(9) Uani 1 1 d . . . . .
H18 H 0.4462 -0.0918 0.3798 0.086 Uiso 1 1 calc R U . . .
C19 C 0.2648(4) -0.2056(2) 0.3158(2) 0.0623(7) Uani 1 1 d . . . . .
C20 C 0.1273(4) -0.2336(2) 0.2425(2) 0.0698(8) Uani 1 1 d . . . . .
H20 H 0.0643 -0.2946 0.2323 0.084 Uiso 1 1 calc R U . . .
C21 C 0.0796(3) -0.1736(2) 0.1834(2) 0.0573(7) Uani 1 1 d . . . . .
H21 H -0.0154 -0.1937 0.1356 0.069 Uiso 1 1 calc R U . . .
C22 C 0.3191(5) -0.2723(3) 0.3773(3) 0.0914(12) Uani 1 1 d . . . . .
H22A H 0.4073 -0.2346 0.4326 0.137 Uiso 1 1 calc R U . . .
H22B H 0.3418 -0.3299 0.3370 0.137 Uiso 1 1 calc R U . . .
H22C H 0.2429 -0.2950 0.4017 0.137 Uiso 1 1 calc R U . . .
C23 C 0.2507(3) 0.34965(19) 0.49091(18) 0.0491(6) Uani 1 1 d . . . . .
C24 C 0.1117(4) 0.3074(2) 0.4878(2) 0.0712(9) Uani 1 1 d . . . . .
H24 H 0.0634 0.2420 0.4459 0.085 Uiso 1 1 calc R U . . .
C25 C 0.0448(4) 0.3631(3) 0.5477(3) 0.0866(11) Uani 1 1 d . . . . .
H25 H -0.0490 0.3343 0.5461 0.104 Uiso 1 1 calc R U . . .
C26 C 0.1125(5) 0.4597(3) 0.6094(2) 0.0783(10) Uani 1 1 d . . . . .
C27 C 0.2505(5) 0.5003(3) 0.6109(3) 0.0922(12) Uani 1 1 d . . . . .
H27 H 0.2981 0.5659 0.6526 0.111 Uiso 1 1 calc R U . . .
C28 C 0.3213(4) 0.4468(2) 0.5525(2) 0.0776(9) Uani 1 1 d . . . . .
H28 H 0.4153 0.4759 0.5546 0.093 Uiso 1 1 calc R U . . .
C29 C 0.0340(7) 0.5206(4) 0.6719(4) 0.1215(17) Uani 1 1 d . . . . .
H29A H -0.0620 0.5230 0.6294 0.182 Uiso 1 1 calc R U . . .
H29B H 0.0930 0.5883 0.7055 0.182 Uiso 1 1 calc R U . . .
H29C H 0.0212 0.4889 0.7202 0.182 Uiso 1 1 calc R U . . .
C30 C 0.2644(3) 0.4165(2) 0.0432(2) 0.0531(6) Uani 1 1 d . . . . .
C31 C 0.2143(4) 0.4396(3) -0.0436(3) 0.0767(9) Uani 1 1 d . . . . .
H31 H 0.1371 0.4741 -0.0538 0.092 Uiso 1 1 calc R U . . .
C32 C 0.2787(5) 0.4116(3) -0.1165(3) 0.0955(12) Uani 1 1 d . . . . .
H32 H 0.2448 0.4294 -0.1744 0.115 Uiso 1 1 calc R U . . .
C33 C 0.3915(5) 0.3584(3) -0.1063(3) 0.0848(11) Uani 1 1 d . . . . .
C34 C 0.4366(5) 0.3349(3) -0.0191(3) 0.0966(13) Uani 1 1 d . . . . .
H34 H 0.5111 0.2982 -0.0096 0.116 Uiso 1 1 calc R U . . .
C35 C 0.3760(4) 0.3636(3) 0.0546(3) 0.0795(10) Uani 1 1 d . . . . .
H35 H 0.4110 0.3468 0.1129 0.095 Uiso 1 1 calc R U . . .
C36 C 0.4612(6) 0.3306(4) -0.1849(4) 0.129(2) Uani 1 1 d . . . . .
H36A H 0.5103 0.2760 -0.1769 0.193 Uiso 1 1 calc R U . . .
H36B H 0.5328 0.3884 -0.1789 0.193 Uiso 1 1 calc R U . . .
H36C H 0.3852 0.3096 -0.2496 0.193 Uiso 1 1 calc R U . . .
H1A H 0.383(3) 0.0378(14) 0.076(2) 0.063(9) Uiso 1 1 d 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 O2 1.4198(19) . ?
S1 O1 1.4258(18) . ?
S1 N1 1.637(2) . ?
S1 C9 1.748(3) . ?
S2 C2 1.767(2) . ?
S2 C16 1.778(2) . ?
S3 O4 1.418(2) . ?
S3 O3 1.426(2) . ?
S3 N2 1.641(2) . ?
S3 C23 1.760(3) . ?
S4 C6 1.772(2) . ?
S4 C30 1.779(3) . ?
N1 C1 1.392(3) . ?
N1 H1A 0.814(17) . ?
N2 C7 1.401(3) . ?
N2 C3 1.484(3) . ?
C1 C2 1.334(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.514(3) . ?
C3 C4 1.529(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.520(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.517(3) . ?
C5 C8 1.527(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.330(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.377(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.365(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(7) . ?
C12 C15 1.524(6) . ?
C13 C14 1.397(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.382(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 C22 1.498(4) . ?
C20 C21 1.384(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.373(4) . ?
C23 C28 1.378(4) . ?
C24 C25 1.379(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(5) . ?
C26 C29 1.517(4) . ?
C27 C28 1.378(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.367(4) . ?
C30 C35 1.371(4) . ?
C31 C32 1.388(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.382(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.370(6) . ?
C33 C36 1.494(5) . ?
C34 C35 1.373(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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
O2 S1 O1 120.06(11) . . ?
O2 S1 N1 106.56(11) . . ?
O1 S1 N1 105.93(11) . . ?
O2 S1 C9 108.93(13) . . ?
O1 S1 C9 108.91(12) . . ?
N1 S1 C9 105.46(12) . . ?
C2 S2 C16 102.77(11) . . ?
O4 S3 O3 120.18(13) . . ?
O4 S3 N2 106.37(11) . . ?
O3 S3 N2 107.58(11) . . ?
O4 S3 C23 109.20(12) . . ?
O3 S3 C23 107.83(12) . . ?
N2 S3 C23 104.61(11) . . ?
C6 S4 C30 101.42(11) . . ?
C1 N1 S1 120.59(17) . . ?
C1 N1 H1A 120(2) . . ?
S1 N1 H1A 112(2) . . ?
C7 N2 C3 118.98(19) . . ?
C7 N2 S3 119.90(16) . . ?
C3 N2 S3 121.01(15) . . ?
C2 C1 N1 126.6(2) . . ?
C2 C1 H1 116.7 . . ?
N1 C1 H1 116.7 . . ?
C1 C2 C3 121.69(19) . . ?
C1 C2 S2 121.87(17) . . ?
C3 C2 S2 116.30(15) . . ?
N2 C3 C2 111.14(18) . . ?
N2 C3 C4 107.90(18) . . ?
C2 C3 C4 112.26(18) . . ?
N2 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C5 C4 C3 113.34(18) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 108.86(19) . . ?
C6 C5 C8 113.3(2) . . ?
C4 C5 C8 110.7(2) . . ?
C6 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
C8 C5 H5 108.0 . . ?
C7 C6 C5 122.4(2) . . ?
C7 C6 S4 116.88(18) . . ?
C5 C6 S4 120.70(17) . . ?
C6 C7 N2 123.4(2) . . ?
C6 C7 H7 118.3 . . ?
N2 C7 H7 118.3 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 121.3(3) . . ?
C14 C9 S1 119.4(2) . . ?
C10 C9 S1 119.2(3) . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 122.5(4) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 118.2(4) . . ?
C13 C12 C15 121.1(6) . . ?
C11 C12 C15 120.7(5) . . ?
C12 C13 C14 122.1(4) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C9 C14 C13 117.6(4) . . ?
C9 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 S2 123.7(2) . . ?
C21 C16 S2 117.65(19) . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 122.4(3) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C20 C19 C18 117.0(3) . . ?
C20 C19 C22 121.9(3) . . ?
C18 C19 C22 121.1(3) . . ?
C19 C20 C21 121.7(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 120.2(3) . . ?
C24 C23 S3 119.4(2) . . ?
C28 C23 S3 120.4(2) . . ?
C23 C24 C25 119.1(3) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.7(3) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C27 C26 C25 118.1(3) . . ?
C27 C26 C29 121.3(4) . . ?
C25 C26 C29 120.6(4) . . ?
C26 C27 C28 121.9(3) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C23 C28 C27 118.9(3) . . ?
C23 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C35 118.4(3) . . ?
C31 C30 S4 119.4(2) . . ?
C35 C30 S4 122.1(2) . . ?
C30 C31 C32 120.0(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 122.4(3) . . ?
C33 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
C34 C33 C32 115.8(3) . . ?
C34 C33 C36 122.6(4) . . ?
C32 C33 C36 121.5(4) . . ?
C33 C34 C35 122.5(4) . . ?
C33 C34 H34 118.7 . . ?
C35 C34 H34 118.7 . . ?
C30 C35 C34 120.8(3) . . ?
C30 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
O2 S1 N1 C1 -32.0(2) . . . . ?
O1 S1 N1 C1 -160.90(19) . . . . ?
C9 S1 N1 C1 83.7(2) . . . . ?
O4 S3 N2 C7 -167.21(17) . . . . ?
O3 S3 N2 C7 -37.2(2) . . . . ?
C23 S3 N2 C7 77.28(19) . . . . ?
O4 S3 N2 C3 8.9(2) . . . . ?
O3 S3 N2 C3 138.90(18) . . . . ?
C23 S3 N2 C3 -106.61(18) . . . . ?
S1 N1 C1 C2 -155.6(2) . . . . ?
N1 C1 C2 C3 -173.3(2) . . . . ?
N1 C1 C2 S2 2.2(3) . . . . ?
C16 S2 C2 C1 96.3(2) . . . . ?
C16 S2 C2 C3 -88.03(18) . . . . ?
C7 N2 C3 C2 87.2(2) . . . . ?
S3 N2 C3 C2 -89.0(2) . . . . ?
C7 N2 C3 C4 -36.3(2) . . . . ?
S3 N2 C3 C4 147.54(16) . . . . ?
C1 C2 C3 N2 -15.2(3) . . . . ?
S2 C2 C3 N2 169.09(15) . . . . ?
C1 C2 C3 C4 105.8(2) . . . . ?
S2 C2 C3 C4 -70.0(2) . . . . ?
N2 C3 C4 C5 57.3(2) . . . . ?
C2 C3 C4 C5 -65.5(2) . . . . ?
C3 C4 C5 C6 -48.4(2) . . . . ?
C3 C4 C5 C8 -173.51(19) . . . . ?
C4 C5 C6 C7 18.6(3) . . . . ?
C8 C5 C6 C7 142.2(2) . . . . ?
C4 C5 C6 S4 -161.65(15) . . . . ?
C8 C5 C6 S4 -38.1(3) . . . . ?
C30 S4 C6 C7 109.9(2) . . . . ?
C30 S4 C6 C5 -69.8(2) . . . . ?
C5 C6 C7 N2 1.6(3) . . . . ?
S4 C6 C7 N2 -178.10(16) . . . . ?
C3 N2 C7 C6 8.2(3) . . . . ?
S3 N2 C7 C6 -175.61(18) . . . . ?
O2 S1 C9 C14 31.7(3) . . . . ?
O1 S1 C9 C14 164.3(2) . . . . ?
N1 S1 C9 C14 -82.3(3) . . . . ?
O2 S1 C9 C10 -152.4(2) . . . . ?
O1 S1 C9 C10 -19.7(3) . . . . ?
N1 S1 C9 C10 93.6(2) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
S1 C9 C10 C11 -175.5(3) . . . . ?
C9 C10 C11 C12 1.7(6) . . . . ?
C10 C11 C12 C13 -2.9(7) . . . . ?
C10 C11 C12 C15 175.8(4) . . . . ?
C11 C12 C13 C14 2.1(7) . . . . ?
C15 C12 C13 C14 -176.6(4) . . . . ?
C10 C9 C14 C13 -1.1(5) . . . . ?
S1 C9 C14 C13 174.8(3) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C2 S2 C16 C17 -30.3(3) . . . . ?
C2 S2 C16 C21 154.9(2) . . . . ?
C21 C16 C17 C18 2.0(4) . . . . ?
S2 C16 C17 C18 -172.8(2) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -2.1(5) . . . . ?
C17 C18 C19 C22 176.3(3) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C22 C19 C20 C21 -177.6(3) . . . . ?
C19 C20 C21 C16 1.9(5) . . . . ?
C17 C16 C21 C20 -3.3(4) . . . . ?
S2 C16 C21 C20 171.8(2) . . . . ?
O4 S3 C23 C24 -47.0(3) . . . . ?
O3 S3 C23 C24 -179.2(2) . . . . ?
N2 S3 C23 C24 66.5(3) . . . . ?
O4 S3 C23 C28 134.6(3) . . . . ?
O3 S3 C23 C28 2.4(3) . . . . ?
N2 S3 C23 C28 -111.9(3) . . . . ?
C28 C23 C24 C25 -0.6(5) . . . . ?
S3 C23 C24 C25 -179.0(3) . . . . ?
C23 C24 C25 C26 0.6(6) . . . . ?
C24 C25 C26 C27 -0.4(6) . . . . ?
C24 C25 C26 C29 177.9(4) . . . . ?
C25 C26 C27 C28 0.1(6) . . . . ?
C29 C26 C27 C28 -178.2(4) . . . . ?
C24 C23 C28 C27 0.3(5) . . . . ?
S3 C23 C28 C27 178.7(3) . . . . ?
C26 C27 C28 C23 -0.1(6) . . . . ?
C6 S4 C30 C31 134.3(3) . . . . ?
C6 S4 C30 C35 -49.5(3) . . . . ?
C35 C30 C31 C32 -1.5(5) . . . . ?
S4 C30 C31 C32 174.8(3) . . . . ?
C30 C31 C32 C33 1.5(6) . . . . ?
C31 C32 C33 C34 -0.2(6) . . . . ?
C31 C32 C33 C36 -178.9(4) . . . . ?
C32 C33 C34 C35 -1.0(6) . . . . ?
C36 C33 C34 C35 177.7(4) . . . . ?
C31 C30 C35 C34 0.4(5) . . . . ?
S4 C30 C35 C34 -175.8(3) . . . . ?
C33 C34 C35 C30 0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C28 H28 O3 0.93 2.58 3.253(4) 129.5 2_666
N1 H1A O1 0.814(17) 2.22(2) 2.949(3) 150(3) 2_655

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.107

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd214475
_database_code_depnum_ccdc_archive 'CCDC 1021015'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O2 S2'
_chemical_formula_weight         345.46

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.6224(10)
_cell_length_b                   14.3505(14)
_cell_length_c                   13.0206(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.158(2)
_cell_angle_gamma                90
_cell_volume                     1757.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2688
_cell_measurement_theta_min      5.587
_cell_measurement_theta_max      48.216

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.311
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10504
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3442
_reflns_number_gt                2718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²+0.2027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.13530(5) 0.06325(4) 0.33963(4) 0.04988(18) Uani 1 1 d . . . . .
S2 S 0.34507(6) 0.09188(4) 0.32427(4) 0.05618(19) Uani 1 1 d . . . . .
N1 N 0.03516(17) 0.06792(11) 0.33345(12) 0.0452(4) Uani 1 1 d . . . . .
O1 O -0.15474(18) 0.13352(12) 0.41299(12) 0.0746(5) Uani 1 1 d . . . . .
O2 O -0.18235(16) -0.02900(11) 0.35676(13) 0.0694(5) Uani 1 1 d . . . . .
C1 C 0.1088(2) -0.00523(13) 0.35813(14) 0.0456(4) Uani 1 1 d . . . . .
H1 H 0.0648 -0.0580 0.3780 0.055 Uiso 1 1 calc R U . . .
C2 C 0.2590(2) -0.00967(14) 0.35657(14) 0.0462(5) Uani 1 1 d . . . . .
C3 C 0.3303(2) -0.08776(15) 0.38774(15) 0.0549(5) Uani 1 1 d . . . . .
H3 H 0.2779 -0.1353 0.4099 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4815(2) -0.10886(19) 0.39185(19) 0.0727(7) Uani 1 1 d . . . . .
H4A H 0.5224 -0.0603 0.3571 0.109 Uiso 1 1 calc R U . . .
H4B H 0.4890 -0.1672 0.3573 0.109 Uiso 1 1 calc R U . . .
H4C H 0.5313 -0.1128 0.4638 0.109 Uiso 1 1 calc R U . . .
C5 C 0.25965(18) 0.11430(13) 0.19173(14) 0.0420(4) Uani 1 1 d . . . . .
C6 C 0.2473(2) 0.20553(13) 0.15740(15) 0.0492(5) Uani 1 1 d . . . . .
H6 H 0.2776 0.2536 0.2047 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1905(2) 0.22605(14) 0.05337(16) 0.0515(5) Uani 1 1 d . . . . .
H7 H 0.1829 0.2879 0.0317 0.062 Uiso 1 1 calc R U . . .
C8 C 0.1448(2) 0.15631(14) -0.01905(15) 0.0474(5) Uani 1 1 d . . . . .
C9 C 0.1584(2) 0.06517(13) 0.01704(15) 0.0492(5) Uani 1 1 d . . . . .
H9 H 0.1285 0.0171 -0.0303 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2143(2) 0.04332(13) 0.12023(16) 0.0464(5) Uani 1 1 d . . . . .
H10 H 0.2217 -0.0186 0.1419 0.056 Uiso 1 1 calc R U . . .
C11 C 0.0813(3) 0.17757(17) -0.13223(17) 0.0716(7) Uani 1 1 d . . . . .
H11A H 0.1197 0.1356 -0.1765 0.107 Uiso 1 1 calc R U . . .
H11B H 0.1038 0.2405 -0.1477 0.107 Uiso 1 1 calc R U . . .
H11C H -0.0200 0.1702 -0.1448 0.107 Uiso 1 1 calc R U . . .
C12 C -0.2159(2) 0.09910(13) 0.21150(15) 0.0441(4) Uani 1 1 d . . . . .
C13 C -0.1454(2) 0.15211(13) 0.15067(15) 0.0474(5) Uani 1 1 d . . . . .
H13 H -0.0512 0.1692 0.1761 0.057 Uiso 1 1 calc R U . . .
C14 C -0.2152(2) 0.17971(14) 0.05191(17) 0.0524(5) Uani 1 1 d . . . . .
H14 H -0.1668 0.2148 0.0106 0.063 Uiso 1 1 calc R U . . .
C15 C -0.3562(2) 0.15626(15) 0.01285(17) 0.0569(6) Uani 1 1 d . . . . .
C16 C -0.4252(2) 0.10412(19) 0.0761(2) 0.0692(7) Uani 1 1 d . . . . .
H16 H -0.5203 0.0887 0.0518 0.083 Uiso 1 1 calc R U . . .
C17 C -0.3567(2) 0.07463(18) 0.17383(19) 0.0644(6) Uani 1 1 d . . . . .
H17 H -0.4044 0.0384 0.2146 0.077 Uiso 1 1 calc R U . . .
C18 C -0.4321(3) 0.18697(19) -0.0949(2) 0.0839(8) Uani 1 1 d . . . . .
H18A H -0.5214 0.2149 -0.0907 0.126 Uiso 1 1 calc R U . . .
H18B H -0.4486 0.1340 -0.1408 0.126 Uiso 1 1 calc R U . . .
H18C H -0.3747 0.2317 -0.1218 0.126 Uiso 1 1 calc R U . . .


_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 1.4281(16) . ?
S1 O2 1.4317(16) . ?
S1 N1 1.6604(16) . ?
S1 C12 1.762(2) . ?
S2 C2 1.770(2) . ?
S2 C5 1.7777(19) . ?
N1 C1 1.269(2) . ?
C1 C2 1.451(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.332(3) . ?
C3 C4 1.475(3) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.380(3) . ?
C5 C10 1.387(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C11 1.503(3) . ?
C9 C10 1.374(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.376(3) . ?
C12 C17 1.385(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 C18 1.504(3) . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 117.29(11) . . ?
O1 S1 N1 105.89(10) . . ?
O2 S1 N1 113.13(9) . . ?
O1 S1 C12 109.49(9) . . ?
O2 S1 C12 109.08(10) . . ?
N1 S1 C12 100.65(8) . . ?
C2 S2 C5 103.64(9) . . ?
C1 N1 S1 117.30(13) . . ?
N1 C1 C2 122.49(17) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.92(18) . . ?
C3 C2 S2 121.88(16) . . ?
C1 C2 S2 118.97(14) . . ?
C2 C3 C4 128.6(2) . . ?
C2 C3 H3 115.7 . . ?
C4 C3 H3 115.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.07(18) . . ?
C6 C5 S2 118.46(14) . . ?
C10 C5 S2 122.31(14) . . ?
C5 C6 C7 120.59(18) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 121.20(18) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 117.27(18) . . ?
C7 C8 C11 121.82(19) . . ?
C9 C8 C11 120.90(19) . . ?
C10 C9 C8 122.41(18) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C5 119.45(17) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.03(19) . . ?
C13 C12 S1 122.29(15) . . ?
C17 C12 S1 117.64(15) . . ?
C12 C13 C14 119.57(18) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 C18 121.0(2) . . ?
C14 C15 C18 121.1(2) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 N1 C1 120.50(16) . . . . ?
O2 S1 N1 C1 -9.28(18) . . . . ?
C12 S1 N1 C1 -125.52(16) . . . . ?
S1 N1 C1 C2 -179.56(13) . . . . ?
N1 C1 C2 C3 177.23(19) . . . . ?
N1 C1 C2 S2 2.6(3) . . . . ?
C5 S2 C2 C3 121.13(17) . . . . ?
C5 S2 C2 C1 -64.44(16) . . . . ?
C1 C2 C3 C4 179.2(2) . . . . ?
S2 C2 C3 C4 -6.3(3) . . . . ?
C2 S2 C5 C6 149.07(15) . . . . ?
C2 S2 C5 C10 -35.56(18) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
S2 C5 C6 C7 175.60(14) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C11 179.33(19) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C11 C8 C9 C10 -179.18(19) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
S2 C5 C10 C9 -175.27(14) . . . . ?
O1 S1 C12 C13 87.59(18) . . . . ?
O2 S1 C12 C13 -142.85(16) . . . . ?
N1 S1 C12 C13 -23.64(17) . . . . ?
O1 S1 C12 C17 -90.35(19) . . . . ?
O2 S1 C12 C17 39.22(19) . . . . ?
N1 S1 C12 C17 158.42(17) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
S1 C12 C13 C14 -178.56(15) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C18 179.7(2) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C18 C15 C16 C17 179.1(2) . . . . ?
C15 C16 C17 C12 1.4(4) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
S1 C12 C17 C16 177.50(19) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

