# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cd16049
_database_code_depnum_ccdc_archive 'CCDC 1449115'
_audit_update_record             
;
2016-01-22 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 N2 O2 S'
_chemical_formula_weight         442.56

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   14.945(2)
_cell_length_b                   16.857(3)
_cell_length_c                   18.059(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4549.7(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1307
_cell_measurement_theta_min      4.511
_cell_measurement_theta_max      34.155

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_T_max  0.7456
_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            25038
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         25.493
_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             4233
_reflns_number_gt                2254
_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)+(0.0479P)²+0.0349P] 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         4233
_refine_ls_number_parameters     290
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.997
_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_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 0.27286(5) 0.11237(4) 0.28330(4) 0.0667(3) Uani 1 1 d . U . . .
N1 N 0.03586(14) 0.22103(12) 0.40148(11) 0.0516(5) Uani 1 1 d . . . . .
N2 N 0.22585(14) 0.19672(12) 0.30098(11) 0.0561(6) Uani 1 1 d . . . . .
O1 O 0.21910(13) 0.05373(11) 0.31970(12) 0.0802(6) Uani 1 1 d . U . . .
O2 O 0.28568(14) 0.10944(13) 0.20489(11) 0.0926(7) Uani 1 1 d . U . . .
C1 C -0.03101(17) 0.27693(16) 0.39373(13) 0.0525(7) Uani 1 1 d . . . . .
C2 C -0.12117(18) 0.27265(18) 0.41191(14) 0.0647(8) Uani 1 1 d . . . . .
H2 H -0.1461 0.2265 0.4311 0.078 Uiso 1 1 calc R U . . .
C3 C -0.1721(2) 0.3396(2) 0.40031(17) 0.0766(9) Uani 1 1 d . . . . .
H3 H -0.2326 0.3387 0.4125 0.092 Uiso 1 1 calc R U . . .
C4 C -0.1358(2) 0.4075(2) 0.37123(18) 0.0813(9) Uani 1 1 d . . . . .
H4 H -0.1725 0.4513 0.3636 0.098 Uiso 1 1 calc R U . . .
C5 C -0.0467(2) 0.41259(17) 0.35313(15) 0.0684(8) Uani 1 1 d . . . . .
H5 H -0.0233 0.4589 0.3330 0.082 Uiso 1 1 calc R U . . .
C6 C 0.00819(18) 0.34639(15) 0.36574(13) 0.0525(7) Uani 1 1 d . . . . .
C7 C 0.10148(18) 0.33121(14) 0.35742(13) 0.0533(7) Uani 1 1 d . . . . .
C8 C 0.17772(19) 0.38219(15) 0.33188(16) 0.0703(8) Uani 1 1 d . . . . .
H8A H 0.1865 0.4255 0.3665 0.084 Uiso 1 1 calc R U . . .
H8B H 0.1638 0.4046 0.2838 0.084 Uiso 1 1 calc R U . . .
C9 C 0.26306(19) 0.33308(16) 0.32669(16) 0.0660(8) Uani 1 1 d . . . . .
H9 H 0.3152 0.3677 0.3203 0.079 Uiso 1 1 calc R U . . .
C10 C 0.2602(2) 0.27012(17) 0.26527(15) 0.0742(9) Uani 1 1 d . . . . .
H10A H 0.2207 0.2867 0.2255 0.089 Uiso 1 1 calc R U . . .
H10B H 0.3195 0.2613 0.2451 0.089 Uiso 1 1 calc R U . . .
C11 C 0.27394(17) 0.28166(15) 0.39549(14) 0.0625(7) Uani 1 1 d . . . . .
H11A H 0.3338 0.2599 0.3993 0.075 Uiso 1 1 calc R U . . .
H11B H 0.2597 0.3106 0.4404 0.075 Uiso 1 1 calc R U . . .
C12 C 0.20497(16) 0.21779(15) 0.37908(13) 0.0515(7) Uani 1 1 d . . . . .
H12 H 0.2092 0.1724 0.4128 0.062 Uiso 1 1 calc R U . . .
C13 C 0.11555(17) 0.25563(14) 0.37975(12) 0.0476(6) Uani 1 1 d . . . . .
C14 C 0.02411(18) 0.13685(15) 0.41655(15) 0.0609(7) Uani 1 1 d . . . . .
H14A H 0.0571 0.1069 0.3797 0.073 Uiso 1 1 calc R U . . .
H14B H -0.0387 0.1238 0.4109 0.073 Uiso 1 1 calc R U . . .
C15 C 0.05414(17) 0.11083(16) 0.49218(17) 0.0579(7) Uani 1 1 d . . . . .
C16 C 0.10912(19) 0.04542(18) 0.49945(19) 0.0753(9) Uani 1 1 d . . . . .
H16 H 0.1306 0.0201 0.4573 0.090 Uiso 1 1 calc R U . . .
C17 C 0.1325(2) 0.0173(2) 0.5681(3) 0.0941(12) Uani 1 1 d . . . . .
H17 H 0.1696 -0.0268 0.5721 0.113 Uiso 1 1 calc R U . . .
C18 C 0.1023(3) 0.0529(3) 0.6290(2) 0.1013(13) Uani 1 1 d . . . . .
H18 H 0.1179 0.0329 0.6752 0.122 Uiso 1 1 calc R U . . .
C19 C 0.0486(3) 0.1188(3) 0.6246(2) 0.1058(12) Uani 1 1 d . . . . .
H19 H 0.0283 0.1434 0.6676 0.127 Uiso 1 1 calc R U . . .
C20 C 0.0245(2) 0.1488(2) 0.55465(19) 0.0819(9) Uani 1 1 d . . . . .
H20 H -0.0111 0.1939 0.5509 0.098 Uiso 1 1 calc R U . . .
C21 C 0.37834(17) 0.11323(15) 0.32584(15) 0.0559(7) Uani 1 1 d . . . . .
C22 C 0.4521(2) 0.14113(18) 0.28727(16) 0.0723(8) Uani 1 1 d . . . . .
H22 H 0.4470 0.1549 0.2376 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5329(2) 0.1483(2) 0.3232(2) 0.0820(9) Uani 1 1 d . . . . .
H23 H 0.5824 0.1665 0.2970 0.098 Uiso 1 1 calc R U . . .
C24 C 0.54231(19) 0.12907(19) 0.39677(19) 0.0724(9) Uani 1 1 d . . . . .
C25 C 0.4688(2) 0.10083(16) 0.43398(16) 0.0672(8) Uani 1 1 d . . . . .
H25 H 0.4742 0.0871 0.4837 0.081 Uiso 1 1 calc R U . . .
C26 C 0.38750(19) 0.09237(15) 0.39951(16) 0.0616(7) Uani 1 1 d . . . . .
H26 H 0.3387 0.0726 0.4256 0.074 Uiso 1 1 calc R U . . .
C27 C 0.6313(2) 0.1382(2) 0.4358(2) 0.1104(13) Uani 1 1 d . . . . .
H27A H 0.6781 0.1431 0.3997 0.166 Uiso 1 1 calc R U . . .
H27B H 0.6422 0.0925 0.4662 0.166 Uiso 1 1 calc R U . . .
H27C H 0.6300 0.1849 0.4663 0.166 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 1.430(2) . ?
S1 O1 1.433(2) . ?
S1 N2 1.618(2) . ?
S1 C21 1.754(3) . ?
N1 C1 1.381(3) . ?
N1 C13 1.383(3) . ?
N1 C14 1.456(3) . ?
N2 C10 1.487(3) . ?
N2 C12 1.488(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.426(3) . ?
C7 C13 1.353(3) . ?
C7 C8 1.500(3) . ?
C8 C9 1.523(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.524(4) . ?
C9 C10 1.536(4) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.481(3) . ?
C12 H12 0.9800 . ?
C14 C15 1.503(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.371(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.332(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.408(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.383(3) . ?
C21 C22 1.386(4) . ?
C22 C23 1.377(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(4) . ?
C24 C27 1.513(4) . ?
C25 C26 1.372(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.37(13) . . ?
O2 S1 N2 106.50(12) . . ?
O1 S1 N2 105.79(12) . . ?
O2 S1 C21 108.28(13) . . ?
O1 S1 C21 107.97(13) . . ?
N2 S1 C21 107.26(11) . . ?
C1 N1 C13 107.9(2) . . ?
C1 N1 C14 126.7(2) . . ?
C13 N1 C14 124.6(2) . . ?
C10 N2 C12 106.55(19) . . ?
C10 N2 S1 119.74(17) . . ?
C12 N2 S1 119.22(16) . . ?
N1 C1 C2 130.0(3) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 122.2(3) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 107.3(2) . . ?
C5 C6 C7 134.2(3) . . ?
C13 C7 C6 106.8(2) . . ?
C13 C7 C8 120.9(2) . . ?
C6 C7 C8 132.3(2) . . ?
C7 C8 C9 110.1(2) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 C11 110.4(2) . . ?
C8 C9 C10 113.4(2) . . ?
C11 C9 C10 101.5(2) . . ?
C8 C9 H9 110.4 . . ?
C11 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
N2 C10 C9 105.8(2) . . ?
N2 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
N2 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C9 99.9(2) . . ?
C12 C11 H11A 111.8 . . ?
C9 C11 H11A 111.8 . . ?
C12 C11 H11B 111.8 . . ?
C9 C11 H11B 111.8 . . ?
H11A C11 H11B 109.5 . . ?
C13 C12 N2 107.45(19) . . ?
C13 C12 C11 107.8(2) . . ?
N2 C12 C11 102.23(19) . . ?
C13 C12 H12 112.9 . . ?
N2 C12 H12 112.9 . . ?
C11 C12 H12 112.9 . . ?
C7 C13 N1 110.4(2) . . ?
C7 C13 C12 122.9(2) . . ?
N1 C13 C12 126.7(2) . . ?
N1 C14 C15 114.7(2) . . ?
N1 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N1 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 119.1(3) . . ?
C20 C15 C14 121.0(3) . . ?
C16 C15 C14 119.8(3) . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 119.2(3) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C26 C21 C22 119.4(3) . . ?
C26 C21 S1 120.6(2) . . ?
C22 C21 S1 119.8(2) . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 118.2(3) . . ?
C25 C24 C27 120.7(3) . . ?
C23 C24 C27 121.1(3) . . ?
C26 C25 C24 121.5(3) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C21 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C10 -45.1(2) . . . . ?
O1 S1 N2 C10 -174.25(19) . . . . ?
C21 S1 N2 C10 70.7(2) . . . . ?
O2 S1 N2 C12 -179.13(18) . . . . ?
O1 S1 N2 C12 51.7(2) . . . . ?
C21 S1 N2 C12 -63.4(2) . . . . ?
C13 N1 C1 C2 -176.1(2) . . . . ?
C14 N1 C1 C2 14.2(4) . . . . ?
C13 N1 C1 C6 0.9(3) . . . . ?
C14 N1 C1 C6 -168.8(2) . . . . ?
N1 C1 C2 C3 177.6(2) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
N1 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
N1 C1 C6 C7 -0.6(3) . . . . ?
C2 C1 C6 C7 176.7(2) . . . . ?
C4 C5 C6 C1 2.3(4) . . . . ?
C4 C5 C6 C7 -176.6(3) . . . . ?
C1 C6 C7 C13 0.1(3) . . . . ?
C5 C6 C7 C13 179.1(3) . . . . ?
C1 C6 C7 C8 -178.5(3) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C13 C7 C8 C9 7.1(3) . . . . ?
C6 C7 C8 C9 -174.5(3) . . . . ?
C7 C8 C9 C11 -45.7(3) . . . . ?
C7 C8 C9 C10 67.4(3) . . . . ?
C12 N2 C10 C9 2.9(3) . . . . ?
S1 N2 C10 C9 -136.19(19) . . . . ?
C8 C9 C10 N2 -91.9(3) . . . . ?
C11 C9 C10 N2 26.5(3) . . . . ?
C8 C9 C11 C12 75.5(3) . . . . ?
C10 C9 C11 C12 -44.9(2) . . . . ?
C10 N2 C12 C13 81.9(2) . . . . ?
S1 N2 C12 C13 -138.72(18) . . . . ?
C10 N2 C12 C11 -31.4(2) . . . . ?
S1 N2 C12 C11 108.0(2) . . . . ?
C9 C11 C12 C13 -65.6(2) . . . . ?
C9 C11 C12 N2 47.4(2) . . . . ?
C6 C7 C13 N1 0.5(3) . . . . ?
C8 C7 C13 N1 179.3(2) . . . . ?
C6 C7 C13 C12 179.9(2) . . . . ?
C8 C7 C13 C12 -1.4(4) . . . . ?
C1 N1 C13 C7 -0.9(3) . . . . ?
C14 N1 C13 C7 169.1(2) . . . . ?
C1 N1 C13 C12 179.8(2) . . . . ?
C14 N1 C13 C12 -10.3(4) . . . . ?
N2 C12 C13 C7 -76.4(3) . . . . ?
C11 C12 C13 C7 33.1(3) . . . . ?
N2 C12 C13 N1 102.8(3) . . . . ?
C11 C12 C13 N1 -147.7(2) . . . . ?
C1 N1 C14 C15 -110.7(3) . . . . ?
C13 N1 C14 C15 81.2(3) . . . . ?
N1 C14 C15 C20 52.1(3) . . . . ?
N1 C14 C15 C16 -130.9(3) . . . . ?
C20 C15 C16 C17 1.5(4) . . . . ?
C14 C15 C16 C17 -175.5(2) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C16 C15 C20 C19 -1.9(4) . . . . ?
C14 C15 C20 C19 175.1(3) . . . . ?
C18 C19 C20 C15 1.0(5) . . . . ?
O2 S1 C21 C26 -160.6(2) . . . . ?
O1 S1 C21 C26 -28.8(2) . . . . ?
N2 S1 C21 C26 84.8(2) . . . . ?
O2 S1 C21 C22 24.7(3) . . . . ?
O1 S1 C21 C22 156.5(2) . . . . ?
N2 S1 C21 C22 -89.9(2) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
S1 C21 C22 C23 174.2(2) . . . . ?
C21 C22 C23 C24 -0.6(5) . . . . ?
C22 C23 C24 C25 1.2(5) . . . . ?
C22 C23 C24 C27 -179.2(3) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C27 C24 C25 C26 179.8(3) . . . . ?
C24 C25 C26 C21 -0.6(4) . . . . ?
C22 C21 C26 C25 1.2(4) . . . . ?
S1 C21 C26 C25 -173.6(2) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

_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_mo_dm15587_0m
_database_code_depnum_ccdc_archive 'CCDC 1414546'
_audit_update_record             
;
2015-07-23 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O2 S2'
_chemical_formula_weight         369.48

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.934(5)
_cell_length_b                   8.1289(14)
_cell_length_c                   17.387(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.645(3)
_cell_angle_gamma                90
_cell_volume                     3546.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2404
_cell_measurement_theta_min      4.514
_cell_measurement_theta_max      45.120

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12382
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         25.997
_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             3478
_reflns_number_gt                2273
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0556P)²+5.1572P] 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         3478
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.020
_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 -0.02744(4) 0.82197(16) 0.04838(6) 0.0894(4) Uani 1 1 d . . . . .
S2 S 0.17061(3) 0.46685(11) 0.21558(5) 0.0627(3) Uani 1 1 d . . . . .
N1 N 0.12917(9) 0.6182(3) 0.19662(14) 0.0563(6) Uani 1 1 d . . . . .
O1 O 0.20502(10) 0.4860(3) 0.16409(15) 0.0852(8) Uani 1 1 d . . . . .
O2 O 0.13948(9) 0.3216(3) 0.21194(15) 0.0780(7) Uani 1 1 d . . . . .
C1 C -0.04188(13) 0.6170(6) 0.05788(19) 0.0768(11) Uani 1 1 d . . . . .
C2 C -0.08291(15) 0.5251(8) 0.0115(2) 0.0957(15) Uani 1 1 d . . . . .
H2 H -0.1072 0.5739 -0.0310 0.115 Uiso 1 1 calc R U . . .
C3 C -0.08764(16) 0.3654(8) 0.0279(3) 0.1042(17) Uani 1 1 d . . . . .
H3 H -0.1154 0.3043 -0.0037 0.125 Uiso 1 1 calc R U . . .
C4 C -0.05185(16) 0.2891(6) 0.0912(3) 0.0970(14) Uani 1 1 d . . . . .
H4 H -0.0561 0.1785 0.1019 0.116 Uiso 1 1 calc R U . . .
C5 C -0.00992(13) 0.3778(5) 0.1382(2) 0.0718(10) Uani 1 1 d . . . . .
H5 H 0.0144 0.3270 0.1800 0.086 Uiso 1 1 calc R U . . .
C6 C -0.00465(12) 0.5434(4) 0.12216(17) 0.0585(8) Uani 1 1 d . . . . .
C7 C 0.03453(12) 0.6587(4) 0.16146(17) 0.0545(7) Uani 1 1 d . . . . .
C8 C 0.02789(13) 0.8107(4) 0.12871(19) 0.0667(9) Uani 1 1 d . . . . .
C9 C 0.06397(17) 0.9525(5) 0.1582(3) 0.0915(12) Uani 1 1 d . . . . .
H9A H 0.0446 1.0370 0.1786 0.110 Uiso 1 1 calc R U . . .
H9B H 0.0762 0.9993 0.1146 0.110 Uiso 1 1 calc R U . . .
C10 C 0.11154(15) 0.8974(4) 0.2233(2) 0.0748(10) Uani 1 1 d . . . . .
H10 H 0.1304 0.9925 0.2518 0.090 Uiso 1 1 calc R U . . .
C11 C 0.09311(14) 0.7814(4) 0.28083(19) 0.0690(9) Uani 1 1 d . . . . .
H11A H 0.1209 0.7631 0.3291 0.083 Uiso 1 1 calc R U . . .
H11B H 0.0614 0.8221 0.2943 0.083 Uiso 1 1 calc R U . . .
C12 C 0.08178(11) 0.6279(4) 0.23001(17) 0.0526(7) Uani 1 1 d . . . . .
H12 H 0.0775 0.5298 0.2606 0.063 Uiso 1 1 calc R U . . .
C13 C 0.14981(14) 0.7878(4) 0.1931(2) 0.0717(10) Uani 1 1 d . . . . .
H13A H 0.1500 0.8167 0.1391 0.086 Uiso 1 1 calc R U . . .
H13B H 0.1858 0.7978 0.2267 0.086 Uiso 1 1 calc R U . . .
C14 C 0.21002(11) 0.4883(4) 0.31367(19) 0.0540(7) Uani 1 1 d . . . . .
C15 C 0.19249(13) 0.4256(5) 0.3762(2) 0.0722(10) Uani 1 1 d . . . . .
H15 H 0.1603 0.3691 0.3668 0.087 Uiso 1 1 calc R U . . .
C16 C 0.22288(14) 0.4471(5) 0.4527(2) 0.0811(11) Uani 1 1 d . . . . .
H16 H 0.2108 0.4051 0.4948 0.097 Uiso 1 1 calc R U . . .
C17 C 0.27078(13) 0.5297(4) 0.4683(2) 0.0657(9) Uani 1 1 d . . . . .
C18 C 0.28719(13) 0.5919(4) 0.4051(2) 0.0692(9) Uani 1 1 d . . . . .
H18 H 0.3193 0.6489 0.4145 0.083 Uiso 1 1 calc R U . . .
C19 C 0.25748(12) 0.5721(4) 0.3285(2) 0.0627(8) Uani 1 1 d . . . . .
H19 H 0.2694 0.6154 0.2866 0.075 Uiso 1 1 calc R U . . .
C20 C 0.30382(16) 0.5520(6) 0.5524(2) 0.0963(13) Uani 1 1 d . . . . .
H20A H 0.3404 0.5690 0.5522 0.144 Uiso 1 1 calc R U . . .
H20B H 0.3010 0.4554 0.5829 0.144 Uiso 1 1 calc R U . . .
H20C H 0.2911 0.6457 0.5757 0.144 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 C1 1.725(5) . ?
S1 C8 1.733(3) . ?
S2 O2 1.422(2) . ?
S2 O1 1.423(3) . ?
S2 N1 1.612(3) . ?
S2 C14 1.761(3) . ?
N1 C13 1.486(4) . ?
N1 C12 1.488(4) . ?
C1 C2 1.381(6) . ?
C1 C6 1.412(4) . ?
C2 C3 1.342(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.424(4) . ?
C7 C8 1.353(4) . ?
C7 C12 1.499(4) . ?
C8 C9 1.492(5) . ?
C9 C10 1.516(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.522(5) . ?
C10 C11 1.536(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.373(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(5) . ?
C17 C20 1.507(5) . ?
C18 C19 1.369(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C1 S1 C8 91.55(16) . . ?
O2 S2 O1 120.11(16) . . ?
O2 S2 N1 106.43(14) . . ?
O1 S2 N1 106.24(15) . . ?
O2 S2 C14 108.00(15) . . ?
O1 S2 C14 107.20(15) . . ?
N1 S2 C14 108.43(14) . . ?
C13 N1 C12 108.0(2) . . ?
C13 N1 S2 119.2(2) . . ?
C12 N1 S2 122.3(2) . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 S1 128.3(4) . . ?
C6 C1 S1 111.3(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 129.5(3) . . ?
C1 C6 C7 111.3(3) . . ?
C8 C7 C6 113.6(3) . . ?
C8 C7 C12 118.6(3) . . ?
C6 C7 C12 127.8(3) . . ?
C7 C8 C9 124.0(3) . . ?
C7 C8 S1 112.3(3) . . ?
C9 C8 S1 123.7(3) . . ?
C8 C9 C10 110.5(3) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C13 113.2(3) . . ?
C9 C10 C11 109.8(3) . . ?
C13 C10 C11 101.7(3) . . ?
C9 C10 H10 110.6 . . ?
C13 C10 H10 110.6 . . ?
C11 C10 H10 110.6 . . ?
C12 C11 C10 99.9(3) . . ?
C12 C11 H11A 111.8 . . ?
C10 C11 H11A 111.8 . . ?
C12 C11 H11B 111.8 . . ?
C10 C11 H11B 111.8 . . ?
H11A C11 H11B 109.5 . . ?
N1 C12 C7 106.8(2) . . ?
N1 C12 C11 102.3(2) . . ?
C7 C12 C11 109.0(3) . . ?
N1 C12 H12 112.7 . . ?
C7 C12 H12 112.7 . . ?
C11 C12 H12 112.7 . . ?
N1 C13 C10 104.8(3) . . ?
N1 C13 H13A 110.8 . . ?
C10 C13 H13A 110.8 . . ?
N1 C13 H13B 110.8 . . ?
C10 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
C19 C14 C15 119.6(3) . . ?
C19 C14 S2 120.2(3) . . ?
C15 C14 S2 120.1(2) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 121.2(3) . . ?
C16 C17 C20 120.9(4) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
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 . . ?

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 S2 N1 C13 -177.8(2) . . . . ?
O1 S2 N1 C13 -48.7(3) . . . . ?
C14 S2 N1 C13 66.3(3) . . . . ?
O2 S2 N1 C12 41.7(3) . . . . ?
O1 S2 N1 C12 170.8(2) . . . . ?
C14 S2 N1 C12 -74.3(2) . . . . ?
C8 S1 C1 C2 -178.9(3) . . . . ?
C8 S1 C1 C6 0.3(3) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
S1 C1 C2 C3 179.6(3) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
S1 C1 C6 C5 -179.5(2) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
S1 C1 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
C1 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C7 C12 2.0(5) . . . . ?
C1 C6 C7 C12 -177.5(3) . . . . ?
C6 C7 C8 C9 -179.2(3) . . . . ?
C12 C7 C8 C9 -2.0(5) . . . . ?
C6 C7 C8 S1 0.8(4) . . . . ?
C12 C7 C8 S1 178.0(2) . . . . ?
C1 S1 C8 C7 -0.7(3) . . . . ?
C1 S1 C8 C9 179.3(3) . . . . ?
C7 C8 C9 C10 6.0(5) . . . . ?
S1 C8 C9 C10 -174.0(3) . . . . ?
C8 C9 C10 C13 69.5(4) . . . . ?
C8 C9 C10 C11 -43.4(4) . . . . ?
C9 C10 C11 C12 74.2(4) . . . . ?
C13 C10 C11 C12 -45.9(3) . . . . ?
C13 N1 C12 C7 87.1(3) . . . . ?
S2 N1 C12 C7 -128.6(2) . . . . ?
C13 N1 C12 C11 -27.3(3) . . . . ?
S2 N1 C12 C11 117.0(2) . . . . ?
C8 C7 C12 N1 -74.5(3) . . . . ?
C6 C7 C12 N1 102.3(3) . . . . ?
C8 C7 C12 C11 35.3(4) . . . . ?
C6 C7 C12 C11 -147.9(3) . . . . ?
C10 C11 C12 N1 44.9(3) . . . . ?
C10 C11 C12 C7 -67.9(3) . . . . ?
C12 N1 C13 C10 -1.8(3) . . . . ?
S2 N1 C13 C10 -147.3(2) . . . . ?
C9 C10 C13 N1 -88.1(3) . . . . ?
C11 C10 C13 N1 29.7(3) . . . . ?
O2 S2 C14 C19 153.7(3) . . . . ?
O1 S2 C14 C19 22.9(3) . . . . ?
N1 S2 C14 C19 -91.4(3) . . . . ?
O2 S2 C14 C15 -28.5(3) . . . . ?
O1 S2 C14 C15 -159.2(3) . . . . ?
N1 S2 C14 C15 86.5(3) . . . . ?
C19 C14 C15 C16 -0.3(5) . . . . ?
S2 C14 C15 C16 -178.2(3) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C15 C16 C17 C20 -179.8(4) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C20 C17 C18 C19 179.9(3) . . . . ?
C17 C18 C19 C14 0.0(5) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
S2 C14 C19 C18 178.3(2) . . . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.043

_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_cd214173
_database_code_depnum_ccdc_archive 'CCDC 995123'
_audit_update_record             
;
2014-04-02 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O2 S2'
_chemical_formula_weight         319.42

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'
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                   16.677(4)
_cell_length_b                   8.1292(16)
_cell_length_c                   11.693(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.956(4)
_cell_angle_gamma                90
_cell_volume                     1565.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3133
_cell_measurement_theta_min      4.945
_cell_measurement_theta_max      55.622

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    0.343
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5753
_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            8555
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.473
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8555
_reflns_number_gt                6410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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)+(0.1244P)²+0.9898P] 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         8555
_refine_ls_number_parameters     210
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2216
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.075
_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_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
S2 S 0.19829(6) 0.28513(12) 0.65679(10) 0.0661(4) Uani 1 1 d . . . . .
N1 N 0.29372(19) 0.2869(3) 0.6410(3) 0.0566(8) Uani 1 1 d . . . . .
O1 O 0.1966(2) 0.3205(4) 0.7769(3) 0.0916(10) Uani 1 1 d . . . . .
O2 O 0.1666(2) 0.1347(3) 0.6065(4) 0.1012(12) Uani 1 1 d . . . . .
C1 C 0.6840(4) 0.2418(9) 0.5665(6) 0.108(2) Uani 1 1 d D . . . .
H1 H 0.7199 0.2052 0.5186 0.129 Uiso 1 1 calc R U . A 1
C2 C 0.7036(3) 0.3463(8) 0.6499(7) 0.108(2) Uani 1 1 d D . . . .
H2 H 0.7549 0.3935 0.6656 0.130 Uiso 1 1 calc R U . B 1
C4 C 0.5691(3) 0.2946(6) 0.6629(5) 0.0822(15) Uani 1 1 d D . . . .
C5 C 0.4899(3) 0.3084(5) 0.7100(4) 0.0743(12) Uani 1 1 d . . . . .
H5A H 0.5007 0.3608 0.7854 0.089 Uiso 1 1 calc R U . . .
H5B H 0.4703 0.1982 0.7215 0.089 Uiso 1 1 calc R U . . .
C6 C 0.4207(3) 0.4060(5) 0.6334(3) 0.0689(11) Uani 1 1 d . . . . .
H6 H 0.4402 0.5144 0.6135 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3917(3) 0.3116(5) 0.5279(4) 0.0747(12) Uani 1 1 d . . . . .
H7 H 0.4200 0.2984 0.4660 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3196(3) 0.2483(5) 0.5338(3) 0.0651(11) Uani 1 1 d . . . . .
H8 H 0.2895 0.1863 0.4754 0.078 Uiso 1 1 calc R U . . .
C9 C 0.3463(2) 0.4231(5) 0.6903(3) 0.0615(10) Uani 1 1 d . . . . .
H9A H 0.3598 0.4124 0.7737 0.074 Uiso 1 1 calc R U . . .
H9B H 0.3201 0.5285 0.6722 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1507(2) 0.4486(4) 0.5759(3) 0.0484(8) Uani 1 1 d . . . . .
C11 C 0.1154(2) 0.4254(5) 0.4623(3) 0.0591(9) Uani 1 1 d . . . . .
H11 H 0.1150 0.3219 0.4283 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0807(2) 0.5576(5) 0.4001(3) 0.0650(10) Uani 1 1 d . . . . .
H12 H 0.0563 0.5414 0.3239 0.078 Uiso 1 1 calc R U . . .
C13 C 0.0809(2) 0.7136(5) 0.4466(3) 0.0580(9) Uani 1 1 d . . . . .
C14 C 0.1178(2) 0.7339(4) 0.5604(3) 0.0606(10) Uani 1 1 d . . . . .
H14 H 0.1195 0.8380 0.5937 0.073 Uiso 1 1 calc R U . . .
C15 C 0.1518(2) 0.6034(4) 0.6249(3) 0.0562(9) Uani 1 1 d . . . . .
H15 H 0.1756 0.6191 0.7014 0.067 Uiso 1 1 calc R U . . .
C16 C 0.0428(3) 0.8568(6) 0.3784(4) 0.0893(14) Uani 1 1 d . . . . .
H16A H 0.0008 0.9023 0.4163 0.134 Uiso 1 1 calc R U . . .
H16B H 0.0200 0.8209 0.3020 0.134 Uiso 1 1 calc R U . . .
H16C H 0.0833 0.9392 0.3730 0.134 Uiso 1 1 calc R U . . .
S1 S 0.5856(2) 0.1788(5) 0.5539(3) 0.0835(9) Uani 0.7 1 d D U P C 1
C3 C 0.6466(7) 0.3803(17) 0.7099(15) 0.062(3) Uani 0.7 1 d D U P C 1
H3 H 0.6531 0.4494 0.7741 0.075 Uiso 0.7 1 calc R U P C 1
S1' S 0.6240(8) 0.3964(17) 0.7232(13) 0.114(4) Uani 0.3 1 d D U P C 2
C3' C 0.6083(19) 0.217(3) 0.555(2) 0.082(9) Uani 0.3 1 d D U P C 2
H3' H 0.5786 0.1621 0.4924 0.099 Uiso 0.3 1 calc R U P C 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O2 1.423(3) . ?
S2 O1 1.438(3) . ?
S2 N1 1.631(3) . ?
S2 C10 1.749(3) . ?
N1 C8 1.422(5) . ?
N1 C9 1.473(5) . ?
C1 C3' 1.27(3) . ?
C1 C2 1.296(9) . ?
C1 S1 1.705(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.296(14) . ?
C2 S1' 1.736(12) . ?
C2 H2 0.9300 . ?
C4 S1' 1.348(14) . ?
C4 C3 1.495(14) . ?
C4 C5 1.513(6) . ?
C4 C3' 1.64(2) . ?
C4 S1 1.642(7) . ?
C5 C6 1.563(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.469(6) . ?
C6 C9 1.504(6) . ?
C6 H6 0.9800 . ?
C7 C8 1.320(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.379(5) . ?
C10 C15 1.381(5) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(5) . ?
C13 C16 1.495(5) . ?
C14 C15 1.372(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 H3 0.9300 . ?
C3' H3' 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S2 O1 120.9(2) . . ?
O2 S2 N1 105.51(19) . . ?
O1 S2 N1 106.07(18) . . ?
O2 S2 C10 108.75(19) . . ?
O1 S2 C10 107.46(18) . . ?
N1 S2 C10 107.52(15) . . ?
C8 N1 C9 105.5(3) . . ?
C8 N1 S2 122.2(3) . . ?
C9 N1 S2 119.6(3) . . ?
C3' C1 C2 108.4(11) . . ?
C2 C1 S1 112.8(5) . . ?
C2 C1 H1 123.6 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 C3 115.3(8) . . ?
C1 C2 S1' 113.8(7) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 H2 122.3 . . ?
S1' C4 C5 109.0(7) . . ?
C3 C4 C5 125.8(7) . . ?
S1' C4 C3' 108.6(10) . . ?
C5 C4 C3' 141.8(10) . . ?
C3 C4 S1 108.3(6) . . ?
C5 C4 S1 125.9(4) . . ?
C4 C5 C6 115.9(3) . . ?
C4 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C9 103.5(3) . . ?
C7 C6 C5 109.5(4) . . ?
C9 C6 C5 112.3(3) . . ?
C7 C6 H6 110.5 . . ?
C9 C6 H6 110.5 . . ?
C5 C6 H6 110.5 . . ?
C8 C7 C6 110.1(4) . . ?
C8 C7 H7 124.9 . . ?
C6 C7 H7 124.9 . . ?
C7 C8 N1 111.3(3) . . ?
C7 C8 H8 124.3 . . ?
N1 C8 H8 124.3 . . ?
N1 C9 C6 103.8(3) . . ?
N1 C9 H9A 111.0 . . ?
C6 C9 H9A 111.0 . . ?
N1 C9 H9B 111.0 . . ?
C6 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C11 C10 C15 120.0(3) . . ?
C11 C10 S2 120.4(3) . . ?
C15 C10 S2 119.5(3) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 122.4(3) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C14 117.4(3) . . ?
C12 C13 C16 122.1(4) . . ?
C14 C13 C16 120.5(4) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 S1 C1 92.0(3) . . ?
C2 C3 C4 111.5(11) . . ?
C2 C3 H3 124.3 . . ?
C4 C3 H3 124.3 . . ?
C4 S1' C2 96.1(7) . . ?
C1 C3' C4 111.5(14) . . ?
C1 C3' H3' 124.2 . . ?
C4 C3' H3' 124.2 . . ?

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 S2 N1 C8 47.4(3) . . . . ?
O1 S2 N1 C8 176.7(3) . . . . ?
C10 S2 N1 C8 -68.6(3) . . . . ?
O2 S2 N1 C9 -176.4(3) . . . . ?
O1 S2 N1 C9 -47.1(3) . . . . ?
C10 S2 N1 C9 67.6(3) . . . . ?
C3' C1 C2 C3 9.5(19) . . . . ?
S1 C1 C2 C3 1.8(10) . . . . ?
C3' C1 C2 S1' 6.4(18) . . . . ?
S1 C1 C2 S1' -1.4(9) . . . . ?
S1' C4 C5 C6 105.5(8) . . . . ?
C3 C4 C5 C6 108.9(9) . . . . ?
C3' C4 C5 C6 -64(2) . . . . ?
S1 C4 C5 C6 -73.0(5) . . . . ?
C4 C5 C6 C7 69.5(5) . . . . ?
C4 C5 C6 C9 -176.2(4) . . . . ?
C9 C6 C7 C8 -13.2(4) . . . . ?
C5 C6 C7 C8 106.7(4) . . . . ?
C6 C7 C8 N1 -1.7(5) . . . . ?
C9 N1 C8 C7 16.3(4) . . . . ?
S2 N1 C8 C7 157.6(3) . . . . ?
C8 N1 C9 C6 -23.3(4) . . . . ?
S2 N1 C9 C6 -165.9(2) . . . . ?
C7 C6 C9 N1 22.0(4) . . . . ?
C5 C6 C9 N1 -96.0(4) . . . . ?
O2 S2 C10 C11 -22.6(4) . . . . ?
O1 S2 C10 C11 -155.0(3) . . . . ?
N1 S2 C10 C11 91.2(3) . . . . ?
O2 S2 C10 C15 160.3(3) . . . . ?
O1 S2 C10 C15 27.9(4) . . . . ?
N1 S2 C10 C15 -85.9(3) . . . . ?
C15 C10 C11 C12 -0.9(6) . . . . ?
S2 C10 C11 C12 -178.0(3) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C11 C12 C13 C16 -179.8(4) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C16 C13 C14 C15 178.9(4) . . . . ?
C13 C14 C15 C10 0.9(6) . . . . ?
C11 C10 C15 C14 0.0(6) . . . . ?
S2 C10 C15 C14 177.1(3) . . . . ?
S1' C4 S1 C1 1.9(9) . . . . ?
C3 C4 S1 C1 -1.5(7) . . . . ?
C5 C4 S1 C1 -179.8(4) . . . . ?
C3' C4 S1 C1 19(4) . . . . ?
C3' C1 S1 C4 -60(8) . . . . ?
C2 C1 S1 C4 0.0(5) . . . . ?
C1 C2 C3 C4 -2.9(14) . . . . ?
S1' C2 C3 C4 59(17) . . . . ?
S1' C4 C3 C2 -168(5) . . . . ?
C5 C4 C3 C2 -178.9(7) . . . . ?
C3' C4 C3 C2 -3.3(16) . . . . ?
S1 C4 C3 C2 2.8(13) . . . . ?
C3 C4 S1' C2 9(4) . . . . ?
C5 C4 S1' C2 179.0(5) . . . . ?
C3' C4 S1' C2 -7.9(15) . . . . ?
S1 C4 S1' C2 -2.5(11) . . . . ?
C1 C2 S1' C4 2.3(11) . . . . ?
C3 C2 S1' C4 -117(18) . . . . ?
C2 C1 C3' C4 -11(2) . . . . ?
S1 C1 C3' C4 112(9) . . . . ?
S1' C4 C3' C1 14(3) . . . . ?
C3 C4 C3' C1 9(2) . . . . ?
C5 C4 C3' C1 -176.8(8) . . . . ?
S1 C4 C3' C1 -151(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
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C11 H11 O1 0.93 2.66 3.383(5) 135.1 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C11 H11 O1 0.93 2.66 3.383(5) 135.1 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C11 H11 O1 0.93 2.66 3.383(5) 135.1 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656
C8 H8 O1 0.93 2.58 3.409(5) 148.3 4_565
C9 H9A S1 0.97 3.00 3.674(6) 127.6 2_656

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

