# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd214407
_database_code_depnum_ccdc_archive 'CCDC 1018373'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 N3 O4 S2'
_chemical_formula_weight         535.66

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.2945(8)
_cell_length_b                   18.1137(16)
_cell_length_c                   14.6463(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.831(2)
_cell_angle_gamma                90
_cell_volume                     2627.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      4.497
_cell_measurement_theta_max      45.227

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6784
_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            15803
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.831
_diffrn_reflns_theta_max         25.994
_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             5169
_reflns_number_gt                3394
_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)+(0.0883P)²+0.2866P] 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         5169
_refine_ls_number_parameters     337
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.26474(8) 0.11967(4) 0.23409(5) 0.0805(3) Uani 1 1 d . . . . .
S2 S 0.35917(7) 0.15818(5) 0.73559(5) 0.0838(3) Uani 1 1 d . . . . .
N1 N 0.2737(2) 0.12037(11) 0.34578(15) 0.0682(6) Uani 1 1 d . . . . .
N2 N 0.36425(19) 0.09076(12) 0.66074(15) 0.0715(6) Uani 1 1 d . . . . .
N3 N 0.2510(3) -0.02677(15) 0.64741(19) 0.0968(8) Uani 1 1 d . . . . .
O1 O 0.4000(2) 0.11972(12) 0.22749(16) 0.1040(7) Uani 1 1 d . . . . .
O2 O 0.1725(2) 0.17615(12) 0.18925(15) 0.1034(7) Uani 1 1 d . . . . .
O3 O 0.4948(2) 0.18169(14) 0.77339(14) 0.1049(7) Uani 1 1 d . . . . .
O4 O 0.2838(2) 0.13001(14) 0.79629(14) 0.1099(8) Uani 1 1 d . . . . .
C1 C 0.3928(2) 0.08657(13) 0.41302(18) 0.0648(6) Uani 1 1 d . . . . .
H1A H 0.4113 0.0386 0.3899 0.078 Uiso 1 1 calc R U . . .
H1B H 0.4715 0.1177 0.4197 0.078 Uiso 1 1 calc R U . . .
C2 C 0.1662(3) 0.14680(16) 0.3846(2) 0.0785(8) Uani 1 1 d . U . . .
H2A H 0.0918 0.1640 0.3328 0.094 Uiso 1 1 calc R U . . .
H2B H 0.1994 0.1886 0.4257 0.094 Uiso 1 1 calc R U . . .
C3 C 0.1149(2) 0.08960(14) 0.43948(18) 0.0684(7) Uani 1 1 d . U . . .
H3A H 0.0568 0.0557 0.3954 0.082 Uiso 1 1 calc R U . . .
H3B H 0.0608 0.1135 0.4757 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2289(2) 0.04514(12) 0.50815(16) 0.0564(6) Uani 1 1 d . . . . .
C5 C 0.3622(2) 0.07875(12) 0.50490(18) 0.0567(6) Uani 1 1 d . . . . .
C6 C 0.4296(2) 0.10442(13) 0.58807(19) 0.0643(6) Uani 1 1 d . . . . .
H6 H 0.5117 0.1290 0.5986 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2388(2) 0.04822(14) 0.61558(17) 0.0663(6) Uani 1 1 d . . . . .
H7 H 0.1590 0.0719 0.6270 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2436(2) -0.07470(16) 0.5751(2) 0.0765(8) Uani 1 1 d . . . . .
C9 C 0.2242(2) -0.03733(13) 0.4896(2) 0.0643(6) Uani 1 1 d . . . . .
C10 C 0.2074(3) -0.07574(16) 0.4067(2) 0.0821(8) Uani 1 1 d . . . . .
H10 H 0.1911 -0.0507 0.3493 0.099 Uiso 1 1 calc R U . . .
C11 C 0.2147(3) -0.15276(19) 0.4088(3) 0.1061(11) Uani 1 1 d . . . . .
H11 H 0.2049 -0.1794 0.3531 0.127 Uiso 1 1 calc R U . . .
C12 C 0.2367(3) -0.18865(19) 0.4946(4) 0.1124(14) Uani 1 1 d . . . . .
H12 H 0.2417 -0.2399 0.4957 0.135 Uiso 1 1 calc R U . . .
C13 C 0.2514(3) -0.15168(19) 0.5777(3) 0.1022(12) Uani 1 1 d . . . . .
H13 H 0.2662 -0.1771 0.6348 0.123 Uiso 1 1 calc R U . . .
C14 C 0.2675(4) -0.0471(2) 0.7449(2) 0.1136(12) Uani 1 1 d . . . . .
H14A H 0.2131 -0.0896 0.7476 0.170 Uiso 1 1 calc R U . . .
H14B H 0.2399 -0.0068 0.7779 0.170 Uiso 1 1 calc R U . . .
H14C H 0.3607 -0.0584 0.7744 0.170 Uiso 1 1 calc R U . . .
C15 C 0.1928(3) 0.03441(17) 0.18905(19) 0.0783(7) Uani 1 1 d . . . . .
C16 C 0.2732(3) -0.02711(19) 0.1885(2) 0.0892(9) Uani 1 1 d . . . . .
H16 H 0.3668 -0.0227 0.2071 0.107 Uiso 1 1 calc R U . . .
C17 C 0.2145(3) -0.0943(2) 0.1606(2) 0.0961(9) Uani 1 1 d . . . . .
H17 H 0.2695 -0.1352 0.1615 0.115 Uiso 1 1 calc R U . . .
C18 C 0.0772(4) -0.1029(2) 0.1315(2) 0.1026(10) Uani 1 1 d . . . . .
C19 C -0.0007(4) -0.0411(2) 0.1318(3) 0.1141(12) Uani 1 1 d . . . . .
H19 H -0.0942 -0.0456 0.1122 0.137 Uiso 1 1 calc R U . . .
C20 C 0.0548(3) 0.0265(2) 0.1600(2) 0.1002(10) Uani 1 1 d . . . . .
H20 H -0.0006 0.0671 0.1594 0.120 Uiso 1 1 calc R U . . .
C21 C 0.0152(5) -0.1783(3) 0.1029(3) 0.1442(16) Uani 1 1 d . . . . .
H21A H 0.0732 -0.2065 0.0748 0.216 Uiso 1 1 calc R U . . .
H21B H -0.0715 -0.1725 0.0579 0.216 Uiso 1 1 calc R U . . .
H21C H 0.0047 -0.2036 0.1581 0.216 Uiso 1 1 calc R U . . .
C22 C 0.2695(3) 0.23002(15) 0.66831(17) 0.0710(7) Uani 1 1 d . . . . .
C23 C 0.1317(3) 0.23633(18) 0.6577(2) 0.0862(8) Uani 1 1 d . . . . .
H23 H 0.0876 0.2029 0.6871 0.103 Uiso 1 1 calc R U . . .
C24 C 0.0618(3) 0.2924(2) 0.6033(3) 0.0958(10) Uani 1 1 d . . . . .
H24 H -0.0303 0.2970 0.5965 0.115 Uiso 1 1 calc R U . . .
C25 C 0.1245(3) 0.34232(19) 0.5585(2) 0.0885(9) Uani 1 1 d . . . . .
C26 C 0.2616(3) 0.33414(17) 0.56895(19) 0.0834(8) Uani 1 1 d . . . . .
H26 H 0.3052 0.3668 0.5381 0.100 Uiso 1 1 calc R U . . .
C27 C 0.3342(3) 0.27914(16) 0.62358(18) 0.0728(7) Uani 1 1 d . . . . .
H27 H 0.4264 0.2748 0.6306 0.087 Uiso 1 1 calc R U . . .
C28 C 0.0474(4) 0.4060(2) 0.5036(3) 0.1302(15) Uani 1 1 d . . . . .
H28A H 0.0155 0.3929 0.4378 0.195 Uiso 1 1 calc R U . . .
H28B H 0.1056 0.4482 0.5104 0.195 Uiso 1 1 calc R U . . .
H28C H -0.0281 0.4175 0.5277 0.195 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 1.422(2) . ?
S1 O2 1.428(2) . ?
S1 N1 1.613(2) . ?
S1 C15 1.761(3) . ?
S2 O3 1.420(2) . ?
S2 O4 1.424(2) . ?
S2 N2 1.651(2) . ?
S2 C22 1.738(3) . ?
N1 C2 1.456(3) . ?
N1 C1 1.480(3) . ?
N2 C6 1.427(3) . ?
N2 C7 1.494(3) . ?
N3 C8 1.356(4) . ?
N3 C7 1.430(3) . ?
N3 C14 1.440(4) . ?
C1 C5 1.470(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.493(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.547(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.514(3) . ?
C4 C9 1.517(3) . ?
C4 C7 1.550(3) . ?
C5 C6 1.312(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C8 C9 1.389(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.368(4) . ?
C10 C11 1.397(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.374(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(5) . ?
C18 C21 1.516(5) . ?
C19 C20 1.367(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.379(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.368(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.386(4) . ?
C25 C28 1.502(5) . ?
C26 C27 1.365(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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 120.58(13) . . ?
O1 S1 N1 106.44(13) . . ?
O2 S1 N1 107.91(12) . . ?
O1 S1 C15 107.14(13) . . ?
O2 S1 C15 107.28(15) . . ?
N1 S1 C15 106.77(12) . . ?
O3 S2 O4 120.61(13) . . ?
O3 S2 N2 105.95(13) . . ?
O4 S2 N2 105.70(14) . . ?
O3 S2 C22 108.08(13) . . ?
O4 S2 C22 109.07(14) . . ?
N2 S2 C22 106.58(11) . . ?
C2 N1 C1 117.15(19) . . ?
C2 N1 S1 124.00(18) . . ?
C1 N1 S1 118.65(15) . . ?
C6 N2 C7 106.60(19) . . ?
C6 N2 S2 118.27(17) . . ?
C7 N2 S2 119.67(16) . . ?
C8 N3 C7 111.9(2) . . ?
C8 N3 C14 125.3(3) . . ?
C7 N3 C14 122.8(3) . . ?
C5 C1 N1 107.70(17) . . ?
C5 C1 H1A 110.2 . . ?
N1 C1 H1A 110.2 . . ?
C5 C1 H1B 110.2 . . ?
N1 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N1 C2 C3 113.6(2) . . ?
N1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 113.24(19) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C9 112.04(17) . . ?
C5 C4 C3 107.67(17) . . ?
C9 C4 C3 114.5(2) . . ?
C5 C4 C7 102.03(18) . . ?
C9 C4 C7 101.97(18) . . ?
C3 C4 C7 118.00(18) . . ?
C6 C5 C1 128.7(2) . . ?
C6 C5 C4 111.6(2) . . ?
C1 C5 C4 119.3(2) . . ?
C5 C6 N2 113.2(2) . . ?
C5 C6 H6 123.4 . . ?
N2 C6 H6 123.4 . . ?
N3 C7 N2 110.9(2) . . ?
N3 C7 C4 105.8(2) . . ?
N2 C7 C4 106.10(16) . . ?
N3 C7 H7 111.3 . . ?
N2 C7 H7 111.3 . . ?
C4 C7 H7 111.3 . . ?
N3 C8 C9 110.8(2) . . ?
N3 C8 C13 128.9(3) . . ?
C9 C8 C13 120.3(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 C4 130.5(2) . . ?
C8 C9 C4 109.2(2) . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 122.3(3) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C8 118.3(3) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 S1 120.0(2) . . ?
C16 C15 S1 121.0(2) . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 117.3(3) . . ?
C17 C18 C21 120.6(4) . . ?
C19 C18 C21 122.0(4) . . ?
C20 C19 C18 122.2(3) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C19 C20 C15 119.9(3) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 120.3(3) . . ?
C27 C22 S2 120.1(2) . . ?
C23 C22 S2 119.6(2) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 121.6(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 118.2(3) . . ?
C24 C25 C28 120.8(3) . . ?
C26 C25 C28 121.0(4) . . ?
C27 C26 C25 121.4(3) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C22 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 H27 120.3 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 C2 156.8(2) . . . . ?
O2 S1 N1 C2 26.0(3) . . . . ?
C15 S1 N1 C2 -89.0(2) . . . . ?
O1 S1 N1 C1 -28.6(2) . . . . ?
O2 S1 N1 C1 -159.34(19) . . . . ?
C15 S1 N1 C1 85.6(2) . . . . ?
O3 S2 N2 C6 -53.4(2) . . . . ?
O4 S2 N2 C6 177.52(18) . . . . ?
C22 S2 N2 C6 61.55(19) . . . . ?
O3 S2 N2 C7 173.78(17) . . . . ?
O4 S2 N2 C7 44.7(2) . . . . ?
C22 S2 N2 C7 -71.27(19) . . . . ?
C2 N1 C1 C5 8.0(3) . . . . ?
S1 N1 C1 C5 -166.98(16) . . . . ?
C1 N1 C2 C3 -54.2(3) . . . . ?
S1 N1 C2 C3 120.5(2) . . . . ?
N1 C2 C3 C4 44.8(4) . . . . ?
C2 C3 C4 C5 5.0(3) . . . . ?
C2 C3 C4 C9 -120.3(2) . . . . ?
C2 C3 C4 C7 119.7(2) . . . . ?
N1 C1 C5 C6 -123.8(3) . . . . ?
N1 C1 C5 C4 48.1(3) . . . . ?
C9 C4 C5 C6 -114.7(2) . . . . ?
C3 C4 C5 C6 118.5(2) . . . . ?
C7 C4 C5 C6 -6.4(2) . . . . ?
C9 C4 C5 C1 72.1(3) . . . . ?
C3 C4 C5 C1 -54.7(3) . . . . ?
C7 C4 C5 C1 -179.54(19) . . . . ?
C1 C5 C6 N2 175.5(2) . . . . ?
C4 C5 C6 N2 3.1(3) . . . . ?
C7 N2 C6 C5 1.8(3) . . . . ?
S2 N2 C6 C5 -136.56(19) . . . . ?
C8 N3 C7 N2 -117.5(3) . . . . ?
C14 N3 C7 N2 63.1(3) . . . . ?
C8 N3 C7 C4 -2.9(3) . . . . ?
C14 N3 C7 C4 177.8(3) . . . . ?
C6 N2 C7 N3 108.8(2) . . . . ?
S2 N2 C7 N3 -113.6(2) . . . . ?
C6 N2 C7 C4 -5.7(2) . . . . ?
S2 N2 C7 C4 131.96(17) . . . . ?
C5 C4 C7 N3 -110.9(2) . . . . ?
C9 C4 C7 N3 5.1(2) . . . . ?
C3 C4 C7 N3 131.4(2) . . . . ?
C5 C4 C7 N2 7.0(2) . . . . ?
C9 C4 C7 N2 122.94(18) . . . . ?
C3 C4 C7 N2 -110.7(2) . . . . ?
C7 N3 C8 C9 -0.8(3) . . . . ?
C14 N3 C8 C9 178.5(3) . . . . ?
C7 N3 C8 C13 179.9(2) . . . . ?
C14 N3 C8 C13 -0.8(5) . . . . ?
N3 C8 C9 C10 -176.8(2) . . . . ?
C13 C8 C9 C10 2.5(3) . . . . ?
N3 C8 C9 C4 4.4(3) . . . . ?
C13 C8 C9 C4 -176.3(2) . . . . ?
C5 C4 C9 C10 -76.0(3) . . . . ?
C3 C4 C9 C10 47.0(3) . . . . ?
C7 C4 C9 C10 175.6(2) . . . . ?
C5 C4 C9 C8 102.7(2) . . . . ?
C3 C4 C9 C8 -134.3(2) . . . . ?
C7 C4 C9 C8 -5.7(2) . . . . ?
C8 C9 C10 C11 -2.4(4) . . . . ?
C4 C9 C10 C11 176.2(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
N3 C8 C13 C12 177.9(3) . . . . ?
C9 C8 C13 C12 -1.3(4) . . . . ?
O1 S1 C15 C20 -160.5(2) . . . . ?
O2 S1 C15 C20 -29.7(3) . . . . ?
N1 S1 C15 C20 85.8(3) . . . . ?
O1 S1 C15 C16 24.1(3) . . . . ?
O2 S1 C15 C16 154.9(2) . . . . ?
N1 S1 C15 C16 -89.6(2) . . . . ?
C20 C15 C16 C17 -0.9(4) . . . . ?
S1 C15 C16 C17 174.5(2) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 -0.4(5) . . . . ?
C16 C17 C18 C21 -178.8(3) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C21 C18 C19 C20 178.2(4) . . . . ?
C18 C19 C20 C15 0.1(6) . . . . ?
C16 C15 C20 C19 0.4(5) . . . . ?
S1 C15 C20 C19 -175.1(3) . . . . ?
O3 S2 C22 C27 29.6(2) . . . . ?
O4 S2 C22 C27 162.4(2) . . . . ?
N2 S2 C22 C27 -83.9(2) . . . . ?
O3 S2 C22 C23 -152.2(2) . . . . ?
O4 S2 C22 C23 -19.4(3) . . . . ?
N2 S2 C22 C23 94.2(2) . . . . ?
C27 C22 C23 C24 -0.8(4) . . . . ?
S2 C22 C23 C24 -179.0(2) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C24 C25 C26 0.5(4) . . . . ?
C23 C24 C25 C28 -176.5(3) . . . . ?
C24 C25 C26 C27 -1.2(4) . . . . ?
C28 C25 C26 C27 175.8(3) . . . . ?
C25 C26 C27 C22 0.9(4) . . . . ?
C23 C22 C27 C26 0.2(4) . . . . ?
S2 C22 C27 C26 178.30(18) . . . . ?

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
C27 H27 O2 0.93 2.60 3.447(4) 151.8 4_666
C14 H14B O4 0.96 2.52 3.288(5) 137.1 .
C14 H14B O4 0.96 2.52 3.288(5) 137.1 .
C27 H27 O2 0.93 2.60 3.447(4) 151.8 4_666
C14 H14B O4 0.96 2.52 3.288(5) 137.1 .
C27 H27 O2 0.93 2.60 3.447(4) 151.8 4_666
C14 H14B O4 0.96 2.52 3.288(5) 137.1 .
C27 H27 O2 0.93 2.60 3.447(4) 151.8 4_666

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.044

_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_cd214332
_database_code_depnum_ccdc_archive 'CCDC 1018374'
_audit_update_record             
;
2014-08-07 deposited with the CCDC.
2015-09-21 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 H24 Cl3 N3 O4 S2'
_chemical_formula_weight         624.96

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'
Cl Cl 0.1484 0.1585 '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                   11.3585(10)
_cell_length_b                   11.9810(10)
_cell_length_c                   13.4380(12)
_cell_angle_alpha                106.420(2)
_cell_angle_beta                 108.985(2)
_cell_angle_gamma                104.217(2)
_cell_volume                     1539.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2861
_cell_measurement_theta_min      5.502
_cell_measurement_theta_max      52.453

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.469
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_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     0.0428
_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         1.745
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6031
_reflns_number_gt                4693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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)+(0.0852P)²+0.2777P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6031
_refine_ls_number_parameters     357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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 0.000 172 59 ' '
_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 0.69666(6) 0.46452(6) 0.42662(5) 0.03859(18) Uani 1 1 d . . . . .
S2 S 0.03178(6) 0.48422(6) 0.18283(5) 0.04067(19) Uani 1 1 d . . . . .
N1 N 0.2370(2) 0.35880(19) -0.01615(16) 0.0362(4) Uani 1 1 d D . . . .
N2 N 0.59108(19) 0.4563(2) 0.30233(16) 0.0380(5) Uani 1 1 d . . . . .
N3 N 0.14660(19) 0.4552(2) 0.14070(16) 0.0379(5) Uani 1 1 d . . . . .
O1 O 0.77062(19) 0.39036(19) 0.40029(17) 0.0540(5) Uani 1 1 d . . . . .
O2 O 0.61619(18) 0.43486(19) 0.48460(15) 0.0495(5) Uani 1 1 d . . . . .
O3 O 0.07462(19) 0.51845(19) 0.30365(15) 0.0522(5) Uani 1 1 d . . . . .
O4 O -0.0073(2) 0.56937(19) 0.13573(17) 0.0558(5) Uani 1 1 d . . . . .
Cl1 Cl 0.42871(17) 0.88963(12) 0.60171(12) 0.1341(6) Uani 1 1 d . . . . .
Cl2 Cl 0.42071(17) 0.77890(12) 0.38037(15) 0.1286(5) Uani 1 1 d . . . . .
Cl3 Cl 0.22821(14) 0.88493(14) 0.40953(17) 0.1366(6) Uani 1 1 d . . . . .
C1 C 0.2455(2) 0.2974(2) -0.11387(19) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.1523(3) 0.2466(2) -0.2277(2) 0.0418(6) Uani 1 1 d . . . . .
H2 H 0.0682 0.2523 -0.2477 0.050 Uiso 1 1 calc R U . . .
C3 C 0.1890(3) 0.1877(2) -0.3090(2) 0.0490(6) Uani 1 1 d . . . . .
H3 H 0.1284 0.1521 -0.3857 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3154(3) 0.1799(3) -0.2792(2) 0.0565(7) Uani 1 1 d . . . . .
H4 H 0.3374 0.1394 -0.3365 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4074(3) 0.2304(3) -0.1679(2) 0.0522(7) Uani 1 1 d . . . . .
H5 H 0.4915 0.2249 -0.1493 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3736(2) 0.2906(2) -0.0822(2) 0.0375(5) Uani 1 1 d . . . . .
C7 C 0.4408(2) 0.3492(2) 0.03968(19) 0.0361(5) Uani 1 1 d . . . . .
C8 C 0.3537(2) 0.3886(2) 0.07760(19) 0.0325(5) Uani 1 1 d . . . . .
C9 C 0.3641(2) 0.4401(2) 0.19379(19) 0.0333(5) Uani 1 1 d . . . . .
C10 C 0.4695(2) 0.4618(2) 0.2911(2) 0.0358(5) Uani 1 1 d . . . . .
H10 H 0.4570 0.4829 0.3580 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6476(2) 0.4768(2) 0.2216(2) 0.0405(5) Uani 1 1 d . . . . .
H11A H 0.7428 0.4929 0.2555 0.049 Uiso 1 1 calc R U . . .
H11B H 0.6375 0.5506 0.2094 0.049 Uiso 1 1 calc R U . . .
C12 C 0.5818(3) 0.3675(3) 0.1082(2) 0.0478(6) Uani 1 1 d . . . . .
H12A H 0.6334 0.3800 0.0646 0.057 Uiso 1 1 calc R U . . .
H12B H 0.5830 0.2920 0.1212 0.057 Uiso 1 1 calc R U . . .
C13 C 0.2553(2) 0.4633(2) 0.21701(19) 0.0357(5) Uani 1 1 d . . . . .
H13 H 0.2644 0.4857 0.2920 0.043 Uiso 1 1 calc R U . . .
C14 C -0.0980(2) 0.3366(3) 0.1086(2) 0.0442(6) Uani 1 1 d . . . . .
C15 C -0.1636(3) 0.2904(3) -0.0094(2) 0.0562(7) Uani 1 1 d . . . . .
H15 H -0.1421 0.3389 -0.0488 0.067 Uiso 1 1 calc R U . . .
C16 C -0.2608(3) 0.1723(4) -0.0678(3) 0.0696(9) Uani 1 1 d . . . . .
H16 H -0.3052 0.1413 -0.1472 0.084 Uiso 1 1 calc R U . . .
C17 C -0.2940(3) 0.0984(3) -0.0114(3) 0.0715(9) Uani 1 1 d . . . . .
C18 C -0.2288(3) 0.1485(4) 0.1067(3) 0.0721(9) Uani 1 1 d . . . . .
H18 H -0.2518 0.1012 0.1465 0.087 Uiso 1 1 calc R U . . .
C19 C -0.1306(3) 0.2665(3) 0.1670(3) 0.0557(7) Uani 1 1 d . . . . .
H19 H -0.0870 0.2982 0.2465 0.067 Uiso 1 1 calc R U . . .
C20 C -0.3991(5) -0.0318(4) -0.0772(5) 0.1197(18) Uani 1 1 d . . . . .
H20A H -0.4826 -0.0279 -0.1210 0.180 Uiso 1 1 calc R U . . .
H20B H -0.4104 -0.0689 -0.0247 0.180 Uiso 1 1 calc R U . . .
H20C H -0.3715 -0.0817 -0.1280 0.180 Uiso 1 1 calc R U . . .
C21 C 0.8046(3) 0.6213(3) 0.5006(2) 0.0458(6) Uani 1 1 d . . . . .
C22 C 0.7579(4) 0.7069(3) 0.5495(3) 0.0687(9) Uani 1 1 d . . . . .
H22 H 0.6702 0.6821 0.5423 0.082 Uiso 1 1 calc R U . . .
C23 C 0.8437(6) 0.8304(4) 0.6095(4) 0.1001(15) Uani 1 1 d . . . . .
H23 H 0.8140 0.8904 0.6426 0.120 Uiso 1 1 calc R U . . .
C24 C 0.9743(6) 0.8652(4) 0.6204(3) 0.1006(17) Uani 1 1 d . . . . .
H24 H 1.0325 0.9484 0.6623 0.121 Uiso 1 1 calc R U . . .
C25 C 1.0179(4) 0.7795(4) 0.5711(3) 0.0866(13) Uani 1 1 d . . . . .
H25 H 1.1058 0.8046 0.5787 0.104 Uiso 1 1 calc R U . . .
C26 C 0.9340(3) 0.6551(3) 0.5094(3) 0.0595(8) Uani 1 1 d . . . . .
H26 H 0.9637 0.5959 0.4749 0.071 Uiso 1 1 calc R U . . .
C27 C 0.3269(4) 0.8050(3) 0.4572(3) 0.0764(10) Uani 1 1 d . . . . .
H27 H 0.2680 0.7236 0.4470 0.092 Uiso 1 1 calc R U . . .
H1 H 0.175(2) 0.378(3) -0.012(2) 0.046(8) 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 O1 1.4151(19) . ?
S1 O2 1.4245(19) . ?
S1 N2 1.6681(19) . ?
S1 C21 1.743(3) . ?
S2 O4 1.4292(19) . ?
S2 O3 1.4326(19) . ?
S2 N3 1.6535(19) . ?
S2 C14 1.750(3) . ?
N1 C1 1.358(3) . ?
N1 C8 1.378(3) . ?
N1 H1 0.805(17) . ?
N2 C10 1.359(3) . ?
N2 C11 1.475(3) . ?
N3 C13 1.283(3) . ?
Cl1 C27 1.728(4) . ?
Cl2 C27 1.731(4) . ?
Cl3 C27 1.730(4) . ?
C1 C2 1.390(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(3) . ?
C7 C8 1.372(3) . ?
C7 C12 1.489(3) . ?
C8 C9 1.460(3) . ?
C9 C10 1.359(3) . ?
C9 C13 1.439(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.498(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C14 C19 1.366(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.370(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(5) . ?
C17 C20 1.503(6) . ?
C18 C19 1.374(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.371(4) . ?
C21 C26 1.380(4) . ?
C22 C23 1.377(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.348(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27 0.9800 . ?

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 120.12(12) . . ?
O1 S1 N2 106.77(11) . . ?
O2 S1 N2 105.51(10) . . ?
O1 S1 C21 109.01(13) . . ?
O2 S1 C21 109.12(13) . . ?
N2 S1 C21 105.26(11) . . ?
O4 S2 O3 118.05(12) . . ?
O4 S2 N3 105.99(11) . . ?
O3 S2 N3 112.10(10) . . ?
O4 S2 C14 109.12(12) . . ?
O3 S2 C14 109.53(12) . . ?
N3 S2 C14 100.61(11) . . ?
C1 N1 C8 109.93(19) . . ?
C1 N1 H1 126(2) . . ?
C8 N1 H1 124(2) . . ?
C10 N2 C11 121.84(18) . . ?
C10 N2 S1 119.18(16) . . ?
C11 N2 S1 117.00(15) . . ?
C13 N3 S2 117.48(17) . . ?
N1 C1 C2 130.6(2) . . ?
N1 C1 C6 107.4(2) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 134.2(2) . . ?
C1 C6 C7 107.0(2) . . ?
C8 C7 C6 107.07(19) . . ?
C8 C7 C12 128.4(2) . . ?
C6 C7 C12 124.5(2) . . ?
C7 C8 N1 108.5(2) . . ?
C7 C8 C9 130.1(2) . . ?
N1 C8 C9 120.9(2) . . ?
C10 C9 C13 111.7(2) . . ?
C10 C9 C8 125.5(2) . . ?
C13 C9 C8 122.5(2) . . ?
C9 C10 N2 127.8(2) . . ?
C9 C10 H10 116.1 . . ?
N2 C10 H10 116.1 . . ?
N2 C11 C12 113.0(2) . . ?
N2 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C7 C12 C11 113.2(2) . . ?
C7 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C7 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C9 124.1(2) . . ?
N3 C13 H13 117.9 . . ?
C9 C13 H13 117.9 . . ?
C19 C14 C15 120.7(3) . . ?
C19 C14 S2 120.0(2) . . ?
C15 C14 S2 119.3(2) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C18 117.8(3) . . ?
C16 C17 C20 120.6(4) . . ?
C18 C17 C20 121.5(4) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C14 C19 C18 119.2(3) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
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 . . ?
C22 C21 C26 122.2(3) . . ?
C22 C21 S1 118.4(2) . . ?
C26 C21 S1 119.4(2) . . ?
C21 C22 C23 118.5(4) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.9(4) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 117.9(4) . . ?
C21 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
Cl1 C27 Cl3 108.6(2) . . ?
Cl1 C27 Cl2 111.2(2) . . ?
Cl3 C27 Cl2 111.5(2) . . ?
Cl1 C27 H27 108.4 . . ?
Cl3 C27 H27 108.4 . . ?
Cl2 C27 H27 108.4 . . ?

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 N2 C10 147.62(19) . . . . ?
O2 S1 N2 C10 18.7(2) . . . . ?
C21 S1 N2 C10 -96.6(2) . . . . ?
O1 S1 N2 C11 -48.1(2) . . . . ?
O2 S1 N2 C11 -176.95(18) . . . . ?
C21 S1 N2 C11 67.7(2) . . . . ?
O4 S2 N3 C13 131.6(2) . . . . ?
O3 S2 N3 C13 1.5(2) . . . . ?
C14 S2 N3 C13 -114.8(2) . . . . ?
C8 N1 C1 C2 178.0(2) . . . . ?
C8 N1 C1 C6 -1.7(3) . . . . ?
N1 C1 C2 C3 -179.0(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 177.9(3) . . . . ?
N1 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N1 C1 C6 C7 0.9(3) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C5 C6 C7 C8 -178.1(3) . . . . ?
C1 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C12 4.7(5) . . . . ?
C1 C6 C7 C12 -177.0(2) . . . . ?
C6 C7 C8 N1 -1.2(3) . . . . ?
C12 C7 C8 N1 175.8(2) . . . . ?
C6 C7 C8 C9 171.7(2) . . . . ?
C12 C7 C8 C9 -11.3(4) . . . . ?
C1 N1 C8 C7 1.9(3) . . . . ?
C1 N1 C8 C9 -171.8(2) . . . . ?
C7 C8 C9 C10 1.5(4) . . . . ?
N1 C8 C9 C10 173.6(2) . . . . ?
C7 C8 C9 C13 -172.6(2) . . . . ?
N1 C8 C9 C13 -0.5(3) . . . . ?
C13 C9 C10 N2 -176.0(2) . . . . ?
C8 C9 C10 N2 9.3(4) . . . . ?
C11 N2 C10 C9 26.1(4) . . . . ?
S1 N2 C10 C9 -170.4(2) . . . . ?
C10 N2 C11 C12 -74.9(3) . . . . ?
S1 N2 C11 C12 121.2(2) . . . . ?
C8 C7 C12 C11 -23.0(4) . . . . ?
C6 C7 C12 C11 153.6(2) . . . . ?
N2 C11 C12 C7 69.0(3) . . . . ?
S2 N3 C13 C9 179.53(18) . . . . ?
C10 C9 C13 N3 176.8(2) . . . . ?
C8 C9 C13 N3 -8.3(4) . . . . ?
O4 S2 C14 C19 -139.1(2) . . . . ?
O3 S2 C14 C19 -8.5(3) . . . . ?
N3 S2 C14 C19 109.7(2) . . . . ?
O4 S2 C14 C15 43.0(2) . . . . ?
O3 S2 C14 C15 173.7(2) . . . . ?
N3 S2 C14 C15 -68.1(2) . . . . ?
C19 C14 C15 C16 -1.0(4) . . . . ?
S2 C14 C15 C16 176.8(2) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 1.8(5) . . . . ?
C15 C16 C17 C20 -178.9(4) . . . . ?
C16 C17 C18 C19 -2.1(5) . . . . ?
C20 C17 C18 C19 178.6(4) . . . . ?
C15 C14 C19 C18 0.7(4) . . . . ?
S2 C14 C19 C18 -177.1(2) . . . . ?
C17 C18 C19 C14 0.9(5) . . . . ?
O1 S1 C21 C22 -170.2(2) . . . . ?
O2 S1 C21 C22 -37.3(2) . . . . ?
N2 S1 C21 C22 75.6(2) . . . . ?
O1 S1 C21 C26 9.0(2) . . . . ?
O2 S1 C21 C26 141.9(2) . . . . ?
N2 S1 C21 C26 -105.2(2) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
S1 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 -0.8(6) . . . . ?
C22 C23 C24 C25 1.2(6) . . . . ?
C23 C24 C25 C26 -0.6(6) . . . . ?
C22 C21 C26 C25 0.8(4) . . . . ?
S1 C21 C26 C25 -178.4(2) . . . . ?
C24 C25 C26 C21 -0.4(5) . . . . ?

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
N1 H1 O4 0.805(17) 2.43(2) 3.048(3) 134(2) 2_565
N1 H1 N3 0.805(17) 2.16(2) 2.729(3) 127(2) .
C27 H27 O3 0.98 2.55 3.401(4) 145.4 .
C15 H15 O4 0.93 2.56 3.409(4) 152.1 2_565
C13 H13 O3 0.93 2.33 2.791(3) 110.2 .
C13 H13 O2 0.93 2.62 3.500(3) 158.4 2_666
C10 H10 O2 0.93 2.55 3.458(3) 165.4 2_666
C2 H2 O4 0.93 2.63 3.267(3) 126.6 2_565
N1 H1 O4 0.805(17) 2.43(2) 3.048(3) 134(2) 2_565
N1 H1 N3 0.805(17) 2.16(2) 2.729(3) 127(2) .
C27 H27 O3 0.98 2.55 3.401(4) 145.4 .
C15 H15 O4 0.93 2.56 3.409(4) 152.1 2_565
C13 H13 O3 0.93 2.33 2.791(3) 110.2 .
C13 H13 O2 0.93 2.62 3.500(3) 158.4 2_666
C10 H10 O2 0.93 2.55 3.458(3) 165.4 2_666
C2 H2 O4 0.93 2.63 3.267(3) 126.6 2_565
C2 H2 O4 0.93 2.63 3.267(3) 126.6 2_565
C10 H10 O2 0.93 2.55 3.458(3) 165.4 2_666
C13 H13 O2 0.93 2.62 3.500(3) 158.4 2_666
C13 H13 O3 0.93 2.33 2.791(3) 110.2 .
C15 H15 O4 0.93 2.56 3.409(4) 152.1 2_565
C27 H27 O3 0.98 2.55 3.401(4) 145.4 .
N1 H1 N3 0.805(17) 2.16(2) 2.729(3) 127(2) .
N1 H1 O4 0.805(17) 2.43(2) 3.048(3) 134(2) 2_565

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4



