# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_dm15739_0m
_database_code_depnum_ccdc_archive 'CCDC 1428608'
_audit_update_record             
;
2015-09-30 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H37 Cl2 N3 O4 S2'
_chemical_formula_weight         698.69

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      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                   8.616(4)
_cell_length_b                   21.777(9)
_cell_length_c                   18.552(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.259(9)
_cell_angle_gamma                90
_cell_volume                     3426(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      4.356
_cell_measurement_theta_max      38.781

_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             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.354
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6788
_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            24817
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.870
_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             6732
_reflns_number_gt                3430
_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)+(0.0616P)²+0.8775P] 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     SHELXL
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6732
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.009
_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 0.74159(11) 0.24413(4) 0.77692(5) 0.0502(3) Uani 1 1 d . . . . .
S2 S 0.79399(12) 0.23635(4) 1.02732(5) 0.0543(3) Uani 1 1 d . . . . .
Cl1 Cl 0.4259(2) 0.04937(11) 0.43011(14) 0.1914(11) Uani 1 1 d . . . . .
Cl2 Cl 0.1071(2) 0.07369(9) 0.36957(9) 0.1333(6) Uani 1 1 d . . . . .
N1 N 0.3644(3) 0.20404(13) 0.83876(15) 0.0464(7) Uani 1 1 d . . . . .
N2 N 0.6317(3) 0.20089(11) 0.81801(14) 0.0405(7) Uani 1 1 d . . . . .
N3 N 0.6484(3) 0.21481(13) 0.96432(15) 0.0492(7) Uani 1 1 d . . . . .
O1 O 0.6449(3) 0.29467(11) 0.74746(15) 0.0692(8) Uani 1 1 d . . . . .
O2 O 0.8836(3) 0.25448(11) 0.82765(13) 0.0592(7) Uani 1 1 d . . . . .
O3 O 0.9337(3) 0.21146(12) 1.00728(13) 0.0638(7) Uani 1 1 d . . . . .
O4 O 0.7786(4) 0.30072(11) 1.03654(15) 0.0731(8) Uani 1 1 d . . . . .
C1 C 0.2842(4) 0.15271(16) 0.85625(19) 0.0459(9) Uani 1 1 d . . . . .
C2 C 0.1736(4) 0.14902(19) 0.9021(2) 0.0553(10) Uani 1 1 d . . . . .
H2 H 0.1473 0.1835 0.9269 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1043(4) 0.0934(2) 0.9099(2) 0.0632(11) Uani 1 1 d . . . . .
H3 H 0.0315 0.0903 0.9413 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1389(5) 0.0423(2) 0.8730(2) 0.0707(12) Uani 1 1 d . . . . .
H4 H 0.0875 0.0054 0.8779 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2520(4) 0.04603(18) 0.8280(2) 0.0622(11) Uani 1 1 d . . . . .
H5 H 0.2779 0.0114 0.8033 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3249(4) 0.10108(16) 0.82047(18) 0.0449(9) Uani 1 1 d . . . . .
C7 C 0.4525(4) 0.11667(15) 0.77741(18) 0.0435(8) Uani 1 1 d . . . . .
C8 C 0.6230(4) 0.09425(14) 0.81177(18) 0.0414(8) Uani 1 1 d . . . . .
H8 H 0.6802 0.0955 0.7706 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6954(4) 0.14745(14) 0.86142(18) 0.0402(8) Uani 1 1 d . . . . .
H9 H 0.8105 0.1467 0.8660 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4666(4) 0.18781(15) 0.78702(18) 0.0437(8) Uani 1 1 d . . . . .
H10 H 0.4342 0.2090 0.7401 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3988(4) 0.25573(16) 0.8881(2) 0.0571(10) Uani 1 1 d . . . . .
H11A H 0.2997 0.2747 0.8936 0.069 Uiso 1 1 calc R U . . .
H11B H 0.4579 0.2857 0.8654 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4913(4) 0.24122(17) 0.9644(2) 0.0579(10) Uani 1 1 d . . . . .
H12A H 0.5034 0.2787 0.9931 0.069 Uiso 1 1 calc R U . . .
H12B H 0.4306 0.2126 0.9883 0.069 Uiso 1 1 calc R U . . .
C13 C 0.6510(4) 0.15116(14) 0.93846(17) 0.0421(8) Uani 1 1 d . . . . .
H13A H 0.5478 0.1329 0.9370 0.051 Uiso 1 1 calc R U . . .
H13B H 0.7266 0.1278 0.9727 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4098(5) 0.09679(18) 0.69725(19) 0.0609(11) Uani 1 1 d . . . . .
H14A H 0.4039 0.0528 0.6946 0.091 Uiso 1 1 calc R U . . .
H14B H 0.4890 0.1111 0.6709 0.091 Uiso 1 1 calc R U . . .
H14C H 0.3095 0.1140 0.6759 0.091 Uiso 1 1 calc R U . . .
C15 C 0.6454(4) 0.02920(15) 0.83939(18) 0.0428(8) Uani 1 1 d . . . . .
C16 C 0.6003(5) 0.00681(17) 0.9025(2) 0.0648(11) Uani 1 1 d . . . . .
H16 H 0.5505 0.0330 0.9308 0.078 Uiso 1 1 calc R U . . .
C17 C 0.6275(5) -0.05331(19) 0.9244(2) 0.0763(13) Uani 1 1 d . . . . .
H17 H 0.5984 -0.0669 0.9676 0.092 Uiso 1 1 calc R U . . .
C18 C 0.6971(5) -0.09306(19) 0.8829(3) 0.0737(13) Uani 1 1 d . . . . .
H18 H 0.7137 -0.1338 0.8972 0.088 Uiso 1 1 calc R U . . .
C19 C 0.7421(5) -0.07255(18) 0.8205(3) 0.0699(12) Uani 1 1 d . . . . .
H19 H 0.7902 -0.0993 0.7921 0.084 Uiso 1 1 calc R U . . .
C20 C 0.7164(4) -0.01221(16) 0.7992(2) 0.0536(10) Uani 1 1 d . . . . .
H20 H 0.7480 0.0010 0.7564 0.064 Uiso 1 1 calc R U . . .
C21 C 0.7889(4) 0.20179(16) 0.70308(19) 0.0470(9) Uani 1 1 d . . . . .
C22 C 0.7027(5) 0.21017(19) 0.6333(2) 0.0616(11) Uani 1 1 d . . . . .
H22 H 0.6249 0.2402 0.6248 0.074 Uiso 1 1 calc R U . . .
C23 C 0.7323(5) 0.1743(2) 0.5773(2) 0.0739(13) Uani 1 1 d . . . . .
H23 H 0.6735 0.1803 0.5307 0.089 Uiso 1 1 calc R U . . .
C24 C 0.8461(6) 0.1296(2) 0.5872(2) 0.0678(12) Uani 1 1 d . . . . .
C25 C 0.9326(5) 0.12184(18) 0.6573(2) 0.0609(11) Uani 1 1 d . . . . .
H25 H 1.0099 0.0916 0.6655 0.073 Uiso 1 1 calc R U . . .
C26 C 0.9065(4) 0.15794(17) 0.7150(2) 0.0542(10) Uani 1 1 d . . . . .
H26 H 0.9673 0.1528 0.7613 0.065 Uiso 1 1 calc R U . . .
C27 C 0.8777(7) 0.0892(2) 0.5251(3) 0.1039(18) Uani 1 1 d . . . . .
H27A H 0.7877 0.0635 0.5088 0.156 Uiso 1 1 calc R U . . .
H27B H 0.9683 0.0639 0.5419 0.156 Uiso 1 1 calc R U . . .
H27C H 0.8972 0.1144 0.4853 0.156 Uiso 1 1 calc R U . . .
C28 C 0.7675(4) 0.20076(17) 1.10939(19) 0.0508(9) Uani 1 1 d . . . . .
C29 C 0.6614(5) 0.22464(19) 1.1495(2) 0.0637(11) Uani 1 1 d . . . . .
H29 H 0.6083 0.2610 1.1351 0.076 Uiso 1 1 calc R U . . .
C30 C 0.6353(5) 0.1942(2) 1.2107(2) 0.0704(12) Uani 1 1 d . . . . .
H30 H 0.5636 0.2105 1.2376 0.085 Uiso 1 1 calc R U . . .
C31 C 0.7108(5) 0.1407(2) 1.2337(2) 0.0613(11) Uani 1 1 d . . . . .
C32 C 0.8223(5) 0.11876(18) 1.1946(2) 0.0609(11) Uani 1 1 d . . . . .
H32 H 0.8798 0.0838 1.2109 0.073 Uiso 1 1 calc R U . . .
C33 C 0.8492(4) 0.14767(18) 1.1323(2) 0.0556(10) Uani 1 1 d . . . . .
H33 H 0.9217 0.1317 1.1057 0.067 Uiso 1 1 calc R U . . .
C34 C 0.6748(6) 0.1066(2) 1.2999(2) 0.0879(15) Uani 1 1 d . . . . .
H34A H 0.6392 0.1351 1.3329 0.132 Uiso 1 1 calc R U . . .
H34B H 0.7684 0.0863 1.3244 0.132 Uiso 1 1 calc R U . . .
H34C H 0.5939 0.0766 1.2844 0.132 Uiso 1 1 calc R U . . .
C35 C 0.2914(7) 0.1028(2) 0.3985(3) 0.119(2) Uani 1 1 d . . . . .
H35A H 0.3247 0.1242 0.3580 0.143 Uiso 1 1 calc R U . . .
H35B H 0.2869 0.1326 0.4369 0.143 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 1.422(3) . ?
S1 O1 1.429(3) . ?
S1 N2 1.620(3) . ?
S1 C21 1.758(4) . ?
S2 O4 1.421(3) . ?
S2 O3 1.428(3) . ?
S2 N3 1.624(3) . ?
S2 C28 1.759(4) . ?
Cl1 C35 1.674(6) . ?
Cl2 C35 1.705(6) . ?
N1 C1 1.383(4) . ?
N1 C11 1.448(4) . ?
N1 C10 1.457(4) . ?
N2 C10 1.464(4) . ?
N2 C9 1.465(4) . ?
N3 C13 1.468(4) . ?
N3 C12 1.471(4) . ?
C1 C6 1.382(4) . ?
C1 C2 1.388(5) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(4) . ?
C7 C14 1.530(5) . ?
C7 C10 1.562(4) . ?
C7 C8 1.571(5) . ?
C8 C15 1.507(4) . ?
C8 C9 1.541(4) . ?
C8 H8 0.9800 . ?
C9 C13 1.546(4) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 C12 1.529(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.381(4) . ?
C15 C16 1.387(5) . ?
C16 C17 1.378(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.381(5) . ?
C21 C22 1.384(5) . ?
C22 C23 1.360(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.389(6) . ?
C24 C27 1.512(6) . ?
C25 C26 1.378(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.380(5) . ?
C28 C33 1.380(5) . ?
C29 C30 1.368(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.365(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.388(5) . ?
C31 C34 1.514(5) . ?
C32 C33 1.372(5) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

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 120.33(17) . . ?
O2 S1 N2 106.67(15) . . ?
O1 S1 N2 106.14(15) . . ?
O2 S1 C21 107.89(16) . . ?
O1 S1 C21 107.83(17) . . ?
N2 S1 C21 107.35(15) . . ?
O4 S2 O3 120.42(17) . . ?
O4 S2 N3 107.16(16) . . ?
O3 S2 N3 106.38(15) . . ?
O4 S2 C28 107.52(17) . . ?
O3 S2 C28 107.66(17) . . ?
N3 S2 C28 107.04(16) . . ?
C1 N1 C11 122.3(3) . . ?
C1 N1 C10 110.2(3) . . ?
C11 N1 C10 121.7(3) . . ?
C10 N2 C9 107.7(2) . . ?
C10 N2 S1 122.5(2) . . ?
C9 N2 S1 121.8(2) . . ?
C13 N3 C12 115.9(3) . . ?
C13 N3 S2 116.9(2) . . ?
C12 N3 S2 118.6(2) . . ?
C6 C1 N1 111.4(3) . . ?
C6 C1 C2 120.5(3) . . ?
N1 C1 C2 128.1(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 121.9(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 129.9(3) . . ?
C1 C6 C7 110.0(3) . . ?
C6 C7 C14 112.3(3) . . ?
C6 C7 C10 102.2(3) . . ?
C14 C7 C10 113.1(3) . . ?
C6 C7 C8 115.6(3) . . ?
C14 C7 C8 110.6(3) . . ?
C10 C7 C8 102.4(3) . . ?
C15 C8 C9 119.3(3) . . ?
C15 C8 C7 119.0(3) . . ?
C9 C8 C7 105.0(2) . . ?
C15 C8 H8 103.8 . . ?
C9 C8 H8 103.8 . . ?
C7 C8 H8 103.8 . . ?
N2 C9 C8 101.3(3) . . ?
N2 C9 C13 109.6(2) . . ?
C8 C9 C13 116.8(3) . . ?
N2 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
C13 C9 H9 109.6 . . ?
N1 C10 N2 110.7(3) . . ?
N1 C10 C7 105.8(3) . . ?
N2 C10 C7 106.8(3) . . ?
N1 C10 H10 111.1 . . ?
N2 C10 H10 111.1 . . ?
C7 C10 H10 111.1 . . ?
N1 C11 C12 116.0(3) . . ?
N1 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
N1 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
N3 C12 C11 114.1(3) . . ?
N3 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N3 C13 C9 111.8(3) . . ?
N3 C13 H13A 109.2 . . ?
C9 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C9 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 116.4(3) . . ?
C20 C15 C8 118.2(3) . . ?
C16 C15 C8 125.4(3) . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 122.1(4) . . ?
C19 C20 H20 118.9 . . ?
C15 C20 H20 118.9 . . ?
C26 C21 C22 119.8(4) . . ?
C26 C21 S1 120.2(3) . . ?
C22 C21 S1 119.9(3) . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 122.2(4) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C23 C24 C25 117.6(4) . . ?
C23 C24 C27 122.2(4) . . ?
C25 C24 C27 120.2(4) . . ?
C26 C25 C24 121.6(4) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C21 119.1(4) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C33 120.0(4) . . ?
C29 C28 S2 120.1(3) . . ?
C33 C28 S2 119.8(3) . . ?
C30 C29 C28 119.2(4) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C31 C30 C29 122.2(4) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C32 117.8(4) . . ?
C30 C31 C34 121.2(4) . . ?
C32 C31 C34 121.0(4) . . ?
C33 C32 C31 121.3(4) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C32 C33 C28 119.3(3) . . ?
C32 C33 H33 120.3 . . ?
C28 C33 H33 120.3 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Cl1 C35 Cl2 113.5(3) . . ?
Cl1 C35 H35A 108.9 . . ?
Cl2 C35 H35A 108.9 . . ?
Cl1 C35 H35B 108.9 . . ?
Cl2 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C10 170.7(2) . . . . ?
O1 S1 N2 C10 41.3(3) . . . . ?
C21 S1 N2 C10 -73.8(3) . . . . ?
O2 S1 N2 C9 -44.3(3) . . . . ?
O1 S1 N2 C9 -173.7(2) . . . . ?
C21 S1 N2 C9 71.2(3) . . . . ?
O4 S2 N3 C13 172.2(2) . . . . ?
O3 S2 N3 C13 42.2(3) . . . . ?
C28 S2 N3 C13 -72.7(3) . . . . ?
O4 S2 N3 C12 -41.1(3) . . . . ?
O3 S2 N3 C12 -171.1(3) . . . . ?
C28 S2 N3 C12 74.0(3) . . . . ?
C11 N1 C1 C6 -152.9(3) . . . . ?
C10 N1 C1 C6 0.6(4) . . . . ?
C11 N1 C1 C2 28.0(5) . . . . ?
C10 N1 C1 C2 -178.5(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
N1 C1 C2 C3 177.9(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
C4 C5 C6 C7 178.1(4) . . . . ?
N1 C1 C6 C5 -176.9(3) . . . . ?
C2 C1 C6 C5 2.3(5) . . . . ?
N1 C1 C6 C7 3.7(4) . . . . ?
C2 C1 C6 C7 -177.1(3) . . . . ?
C5 C6 C7 C14 53.2(5) . . . . ?
C1 C6 C7 C14 -127.5(3) . . . . ?
C5 C6 C7 C10 174.7(4) . . . . ?
C1 C6 C7 C10 -6.0(4) . . . . ?
C5 C6 C7 C8 -75.1(5) . . . . ?
C1 C6 C7 C8 104.3(3) . . . . ?
C6 C7 C8 C15 46.9(4) . . . . ?
C14 C7 C8 C15 -82.1(4) . . . . ?
C10 C7 C8 C15 157.1(3) . . . . ?
C6 C7 C8 C9 -89.8(3) . . . . ?
C14 C7 C8 C9 141.2(3) . . . . ?
C10 C7 C8 C9 20.4(3) . . . . ?
C10 N2 C9 C8 41.2(3) . . . . ?
S1 N2 C9 C8 -108.2(3) . . . . ?
C10 N2 C9 C13 -82.8(3) . . . . ?
S1 N2 C9 C13 127.7(2) . . . . ?
C15 C8 C9 N2 -173.9(3) . . . . ?
C7 C8 C9 N2 -37.4(3) . . . . ?
C15 C8 C9 C13 -54.8(4) . . . . ?
C7 C8 C9 C13 81.6(3) . . . . ?
C1 N1 C10 N2 -119.7(3) . . . . ?
C11 N1 C10 N2 34.0(4) . . . . ?
C1 N1 C10 C7 -4.4(4) . . . . ?
C11 N1 C10 C7 149.2(3) . . . . ?
C9 N2 C10 N1 85.8(3) . . . . ?
S1 N2 C10 N1 -125.0(2) . . . . ?
C9 N2 C10 C7 -28.8(3) . . . . ?
S1 N2 C10 C7 120.4(2) . . . . ?
C6 C7 C10 N1 6.1(3) . . . . ?
C14 C7 C10 N1 127.0(3) . . . . ?
C8 C7 C10 N1 -113.9(3) . . . . ?
C6 C7 C10 N2 124.0(3) . . . . ?
C14 C7 C10 N2 -115.1(3) . . . . ?
C8 C7 C10 N2 4.0(3) . . . . ?
C1 N1 C11 C12 56.5(4) . . . . ?
C10 N1 C11 C12 -93.9(4) . . . . ?
C13 N3 C12 C11 -72.3(4) . . . . ?
S2 N3 C12 C11 140.7(3) . . . . ?
N1 C11 C12 N3 60.9(4) . . . . ?
C12 N3 C13 C9 106.6(3) . . . . ?
S2 N3 C13 C9 -105.8(3) . . . . ?
N2 C9 C13 N3 -34.4(4) . . . . ?
C8 C9 C13 N3 -148.9(3) . . . . ?
C9 C8 C15 C20 -122.4(3) . . . . ?
C7 C8 C15 C20 107.1(4) . . . . ?
C9 C8 C15 C16 57.7(5) . . . . ?
C7 C8 C15 C16 -72.8(5) . . . . ?
C20 C15 C16 C17 1.0(6) . . . . ?
C8 C15 C16 C17 -179.0(4) . . . . ?
C15 C16 C17 C18 -1.5(7) . . . . ?
C16 C17 C18 C19 1.2(7) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C18 C19 C20 C15 0.0(6) . . . . ?
C16 C15 C20 C19 -0.3(6) . . . . ?
C8 C15 C20 C19 179.8(4) . . . . ?
O2 S1 C21 C26 35.3(3) . . . . ?
O1 S1 C21 C26 166.7(3) . . . . ?
N2 S1 C21 C26 -79.3(3) . . . . ?
O2 S1 C21 C22 -148.0(3) . . . . ?
O1 S1 C21 C22 -16.6(3) . . . . ?
N2 S1 C21 C22 97.4(3) . . . . ?
C26 C21 C22 C23 1.3(6) . . . . ?
S1 C21 C22 C23 -175.4(3) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C22 C23 C24 C25 -0.3(6) . . . . ?
C22 C23 C24 C27 179.2(4) . . . . ?
C23 C24 C25 C26 -0.5(6) . . . . ?
C27 C24 C25 C26 180.0(4) . . . . ?
C24 C25 C26 C21 1.6(6) . . . . ?
C22 C21 C26 C25 -2.0(5) . . . . ?
S1 C21 C26 C25 174.6(3) . . . . ?
O4 S2 C28 C29 35.4(4) . . . . ?
O3 S2 C28 C29 166.5(3) . . . . ?
N3 S2 C28 C29 -79.5(3) . . . . ?
O4 S2 C28 C33 -146.8(3) . . . . ?
O3 S2 C28 C33 -15.7(3) . . . . ?
N3 S2 C28 C33 98.3(3) . . . . ?
C33 C28 C29 C30 -1.8(6) . . . . ?
S2 C28 C29 C30 176.0(3) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C29 C30 C31 C32 2.7(6) . . . . ?
C29 C30 C31 C34 -177.5(4) . . . . ?
C30 C31 C32 C33 -3.8(6) . . . . ?
C34 C31 C32 C33 176.4(4) . . . . ?
C31 C32 C33 C28 2.1(6) . . . . ?
C29 C28 C33 C32 0.8(6) . . . . ?
S2 C28 C33 C32 -177.0(3) . . . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.046

_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_cd2335
_database_code_depnum_ccdc_archive 'CCDC 994520'
_audit_update_record             
;
2014-03-31 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36  N12 O12 Cl3 Cu3'
_chemical_formula_weight         981.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   24.106(3)
_cell_length_b                   8.4201(10)
_cell_length_c                   20.584(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4178.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      5.204
_cell_measurement_theta_max      48.400

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.606
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_type   sadabs
_exptl_absorpt_correction_T_min  0.0656
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24306
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_sigmaI/netI    0.1188
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         28.30
_reflns_number_total             9454
_reflns_number_gt                4145
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0982P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_number_reflns         9454
_refine_ls_number_parameters     495
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.846
_refine_ls_shift/su_max          0.322
_refine_ls_shift/su_mean         0.054

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.95648(5) 0.78417(14) 0.50417(6) 0.0572(4) Uani 1 1 d . . .
Cu2 Cu 0.03999(5) 0.29688(15) 0.34780(4) 0.0506(3) Uani 1 1 d . . .
Cu3 Cu 0.70905(5) 0.80142(13) 0.67066(7) 0.0556(3) Uani 1 1 d . . .
Cl1 Cl 0.7950(2) 0.2361(11) 0.5071(4) 0.219(3) Uani 1 1 d . . .
Cl2 Cl 0.5422(4) 0.235(2) 0.6746(9) 0.403(8) Uani 1 1 d . . .
Cl3 Cl 0.7798(13) 0.255(6) 0.831(3) 1.23(4) Uiso 1 1 d . . .
O1 O 0.8221(4) 0.2844(13) 0.5645(4) 0.113(4) Uani 1 1 d . . .
O2 O 0.8209(4) 0.2878(12) 0.4523(4) 0.098(3) Uani 1 1 d . . .
O3 O 0.7420(3) 0.2999(10) 0.5100(5) 0.093(3) Uani 1 1 d . . .
O4 O 0.7900(6) 0.0670(8) 0.5067(8) 0.183(6) Uani 1 1 d . . .
O5 O 0.5681(5) 0.3036(16) 0.6168(7) 0.146(5) Uani 1 1 d . . .
O6 O 0.5683(6) 0.2866(17) 0.7298(6) 0.149(6) Uani 1 1 d . . .
O7 O 0.4874(3) 0.2933(11) 0.6720(6) 0.115(3) Uani 1 1 d . . .
O8 O 0.5449(10) 0.0691(17) 0.6669(17) 0.344(19) Uani 1 1 d . . .
O9 O 0.7406(4) 0.2507(15) 0.8316(5) 0.139(5) Uani 1 1 d . . .
O10 O 0.8236(5) 0.2884(16) 0.7849(6) 0.135(5) Uani 1 1 d . . .
O11 O 0.8094(8) 0.0791(19) 0.8302(10) 0.258(10) Uani 1 1 d . . .
O12 O 0.8203(5) 0.2778(12) 0.8926(5) 0.112(4) Uani 1 1 d . . .
N1 N 0.9135(3) 0.8692(11) 0.5801(4) 0.053(2) Uani 1 1 d . . .
N2 N 0.9554(3) 0.5527(9) 0.5063(5) 0.055(2) Uani 1 1 d . . .
N3 N 1.0341(3) 0.8673(9) 0.5088(4) 0.0557(18) Uani 1 1 d . . .
N4 N 0.9189(3) 0.8736(11) 0.4244(4) 0.061(2) Uani 1 1 d . . .
N5 N -0.0361(3) 0.3781(10) 0.3416(4) 0.061(2) Uani 1 1 d . . .
N6 N 0.0767(3) 0.3836(9) 0.4273(3) 0.0467(18) Uani 1 1 d . . .
N7 N 0.0406(4) 0.0645(11) 0.3448(5) 0.067(3) Uani 1 1 d . . .
N8 N 0.0804(3) 0.3790(9) 0.2711(4) 0.053(2) Uani 1 1 d . . .
N9 N 0.7089(3) 1.0418(12) 0.6702(6) 0.066(2) Uani 1 1 d . . .
N10 N 0.7490(4) 0.7290(10) 0.5922(5) 0.063(3) Uani 1 1 d . . .
N11 N 0.7465(4) 0.7378(10) 0.7517(5) 0.061(2) Uani 1 1 d . . .
N12 N 0.6306(3) 0.7349(9) 0.6715(5) 0.0593(18) Uani 1 1 d . . .
C1 C 0.8909(4) 0.9277(12) 0.6195(5) 0.053(2) Uani 1 1 d . . .
C2 C 0.8613(4) 1.0000(13) 0.6760(8) 0.079(3) Uani 1 1 d . . .
H2A H 0.8736 0.9504 0.7154 0.119 Uiso 1 1 calc R . .
H2B H 0.8221 0.9845 0.6711 0.119 Uiso 1 1 calc R . .
H2C H 0.8692 1.1117 0.6777 0.119 Uiso 1 1 calc R . .
C3 C 0.9558(3) 0.4113(9) 0.5082(6) 0.042(2) Uani 1 1 d . . .
C4 C 0.9577(5) 0.2469(8) 0.5122(8) 0.063(4) Uani 1 1 d . . .
H4A H 0.9764 0.2050 0.4748 0.095 Uiso 1 1 calc R . .
H4B H 0.9206 0.2054 0.5140 0.095 Uiso 1 1 calc R . .
H4C H 0.9775 0.2164 0.5508 0.095 Uiso 1 1 calc R . .
C5 C 1.0772(3) 0.9237(10) 0.5063(5) 0.053(2) Uani 1 1 d . . .
C6 C 1.1293(4) 0.9852(11) 0.5043(8) 0.070(3) Uani 1 1 d . . .
H6A H 1.1516 0.9364 0.5374 0.105 Uiso 1 1 calc R . .
H6B H 1.1276 1.0977 0.5117 0.105 Uiso 1 1 calc R . .
H6C H 1.1454 0.9650 0.4625 0.105 Uiso 1 1 calc R . .
C7 C 0.8953(4) 0.9365(12) 0.3832(5) 0.056(3) Uani 1 1 d . . .
C8 C 0.8610(5) 1.0017(15) 0.3351(8) 0.091(4) Uani 1 1 d . . .
H8A H 0.8248 0.9541 0.3376 0.137 Uiso 1 1 calc R . .
H8B H 0.8767 0.9815 0.2931 0.137 Uiso 1 1 calc R . .
H8C H 0.8579 1.1142 0.3417 0.137 Uiso 1 1 calc R . .
C9 C -0.0780(4) 0.4352(10) 0.3341(4) 0.050(2) Uani 1 1 d . . .
C10 C -0.1346(4) 0.5152(13) 0.3248(6) 0.066(3) Uani 1 1 d . . .
H10A H -0.1317 0.6260 0.3353 0.098 Uiso 1 1 calc R . .
H10B H -0.1614 0.4659 0.3528 0.098 Uiso 1 1 calc R . .
H10C H -0.1462 0.5037 0.2804 0.098 Uiso 1 1 calc R . .
C11 C 0.1010(4) 0.4333(11) 0.4674(4) 0.050(2) Uani 1 1 d . . .
C12 C 0.1310(5) 0.5091(11) 0.5232(6) 0.073(4) Uani 1 1 d . . .
H12A H 0.1425 0.6143 0.5111 0.110 Uiso 1 1 calc R . .
H12B H 0.1630 0.4468 0.5340 0.110 Uiso 1 1 calc R . .
H12C H 0.1067 0.5149 0.5601 0.110 Uiso 1 1 calc R . .
C13 C 0.0404(4) -0.0615(15) 0.3406(5) 0.057(3) Uani 1 1 d . . .
C14 C 0.0435(5) -0.2351(14) 0.3387(6) 0.082(5) Uani 1 1 d . . .
H14A H 0.0750 -0.2669 0.3133 0.122 Uiso 1 1 calc R . .
H14B H 0.0103 -0.2769 0.3195 0.122 Uiso 1 1 calc R . .
H14C H 0.0473 -0.2755 0.3821 0.122 Uiso 1 1 calc R . .
C15 C 0.1015(4) 0.4373(10) 0.2259(4) 0.042(2) Uani 1 1 d . . .
C16 C 0.1253(4) 0.5068(14) 0.1705(7) 0.085(4) Uani 1 1 d . . .
H16A H 0.1474 0.4294 0.1481 0.127 Uiso 1 1 calc R . .
H16B H 0.1483 0.5944 0.1834 0.127 Uiso 1 1 calc R . .
H16C H 0.0964 0.5443 0.1423 0.127 Uiso 1 1 calc R . .
C17 C 0.7109(4) 1.1757(12) 0.6723(7) 0.058(3) Uani 1 1 d . . .
C18 C 0.7116(4) 1.3493(10) 0.6717(7) 0.072(3) Uani 1 1 d . . .
H18A H 0.7341 1.3857 0.6362 0.108 Uiso 1 1 calc R . .
H18B H 0.7268 1.3877 0.7118 0.108 Uiso 1 1 calc R . .
H18C H 0.6745 1.3884 0.6665 0.108 Uiso 1 1 calc R . .
C19 C 0.7713(4) 0.7091(12) 0.5459(5) 0.053(3) Uani 1 1 d . . .
C20 C 0.7985(4) 0.6836(15) 0.4839(5) 0.071(3) Uani 1 1 d . . .
H20A H 0.7889 0.5805 0.4676 0.106 Uiso 1 1 calc R . .
H20B H 0.8380 0.6898 0.4896 0.106 Uiso 1 1 calc R . .
H20C H 0.7868 0.7634 0.4537 0.106 Uiso 1 1 calc R . .
C21 C 0.7683(4) 0.7268(12) 0.8026(5) 0.054(3) Uani 1 1 d . . .
C22 C 0.7982(5) 0.7110(17) 0.8603(5) 0.082(4) Uani 1 1 d . . .
H22A H 0.8202 0.6160 0.8587 0.122 Uiso 1 1 calc R . .
H22B H 0.7729 0.7049 0.8963 0.122 Uiso 1 1 calc R . .
H22C H 0.8221 0.8013 0.8658 0.122 Uiso 1 1 calc R . .
C23 C 0.5845(4) 0.7200(10) 0.6747(6) 0.055(2) Uani 1 1 d . . .
C24 C 0.5252(4) 0.6991(15) 0.6748(7) 0.090(4) Uani 1 1 d . . .
H24A H 0.5155 0.6127 0.6466 0.135 Uiso 1 1 calc R . .
H24B H 0.5077 0.7947 0.6598 0.135 Uiso 1 1 calc R . .
H24C H 0.5129 0.6759 0.7181 0.135 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.949(7) . ?
Cu1 N3 2.000(7) . ?
Cu1 N1 2.008(8) . ?
Cu1 N4 2.021(9) . ?
Cu2 N7 1.957(10) . ?
Cu2 N5 1.961(7) . ?
Cu2 N8 1.980(8) . ?
Cu2 N6 1.998(8) . ?
Cu3 N11 1.972(10) . ?
Cu3 N12 1.973(7) . ?
Cu3 N10 1.976(10) . ?
Cu3 N9 2.024(10) . ?
Cl1 O2 1.362(11) . ?
Cl1 O3 1.388(8) . ?
Cl1 O1 1.409(10) . ?
Cl1 O4 1.429(10) . ?
Cl2 O6 1.37(2) . ?
Cl2 O8 1.41(2) . ?
Cl2 O7 1.409(12) . ?
Cl2 O5 1.461(18) . ?
Cl3 O9 0.94(3) . ?
Cl3 O10 1.44(4) . ?
Cl3 O12 1.62(5) . ?
Cl3 O11 1.64(5) . ?
N1 C1 1.094(11) . ?
N2 C3 1.192(9) . ?
N3 C5 1.144(9) . ?
N4 C7 1.151(11) . ?
N5 C9 1.129(10) . ?
N6 C11 1.095(10) . ?
N7 C13 1.065(12) . ?
N8 C15 1.169(10) . ?
N9 C17 1.129(11) . ?
N10 C19 1.109(12) . ?
N11 C21 1.176(13) . ?
N12 C23 1.120(10) . ?
C1 C2 1.493(16) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.388(10) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.359(13) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.401(15) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.535(13) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.500(13) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.464(14) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.403(15) . ?
C16 H16A 0.9603 . ?
C16 H16B 0.9603 . ?
C16 H16C 0.9603 . ?
C17 C18 1.462(13) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.449(14) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.396(14) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.440(12) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
N2 Cu1 N3 111.2(3) . . ?
N2 Cu1 N1 109.4(4) . . ?
N3 Cu1 N1 108.7(3) . . ?
N2 Cu1 N4 112.6(4) . . ?
N3 Cu1 N4 109.2(3) . . ?
N1 Cu1 N4 105.6(3) . . ?
N7 Cu2 N5 110.7(4) . . ?
N7 Cu2 N8 108.7(4) . . ?
N5 Cu2 N8 106.7(3) . . ?
N7 Cu2 N6 112.8(4) . . ?
N5 Cu2 N6 109.8(3) . . ?
N8 Cu2 N6 107.9(3) . . ?
N11 Cu3 N12 110.8(4) . . ?
N11 Cu3 N10 112.6(3) . . ?
N12 Cu3 N10 112.8(4) . . ?
N11 Cu3 N9 106.0(4) . . ?
N12 Cu3 N9 106.4(3) . . ?
N10 Cu3 N9 107.8(4) . . ?
O2 Cl1 O3 109.6(8) . . ?
O2 Cl1 O1 113.0(7) . . ?
O3 Cl1 O1 106.2(8) . . ?
O2 Cl1 O4 110.5(10) . . ?
O3 Cl1 O4 108.0(8) . . ?
O1 Cl1 O4 109.4(10) . . ?
O6 Cl2 O8 113(2) . . ?
O6 Cl2 O7 110.7(14) . . ?
O8 Cl2 O7 112.4(17) . . ?
O6 Cl2 O5 110.9(13) . . ?
O8 Cl2 O5 106.2(18) . . ?
O7 Cl2 O5 103.5(14) . . ?
O9 Cl3 O10 139(5) . . ?
O9 Cl3 O12 126(5) . . ?
O10 Cl3 O12 93(2) . . ?
O9 Cl3 O11 114(4) . . ?
O10 Cl3 O11 82(2) . . ?
O12 Cl3 O11 81(2) . . ?
C1 N1 Cu1 174.1(9) . . ?
C3 N2 Cu1 178.8(9) . . ?
C5 N3 Cu1 173.2(8) . . ?
C7 N4 Cu1 172.9(9) . . ?
C9 N5 Cu2 173.6(8) . . ?
C11 N6 Cu2 173.4(7) . . ?
C13 N7 Cu2 177.1(12) . . ?
C15 N8 Cu2 174.8(8) . . ?
C17 N9 Cu3 176.4(12) . . ?
C19 N10 Cu3 170.6(9) . . ?
C21 N11 Cu3 168.6(8) . . ?
C23 N12 Cu3 169.5(8) . . ?
N1 C1 C2 176.5(11) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.4 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C4 177.7(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 C6 177.6(10) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.3 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 173.1(11) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.6 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 C10 179.0(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.3 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N6 C11 C12 176.0(11) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.6 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N7 C13 C14 175.5(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N8 C15 C16 178.3(9) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 109.4 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.4 . . ?
H16B C16 H16C 109.4 . . ?
N9 C17 C18 176.7(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N10 C19 C20 177.8(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N11 C21 C22 175.3(12) . . ?
C21 C22 H22A 109.4 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N12 C23 C24 176.7(15) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N2 Cu1 N1 C1 -177(100) . . . . ?
N3 Cu1 N1 C1 61(7) . . . . ?
N4 Cu1 N1 C1 -56(7) . . . . ?
N3 Cu1 N2 C3 24(51) . . . . ?
N1 Cu1 N2 C3 -97(51) . . . . ?
N4 Cu1 N2 C3 146(51) . . . . ?
N2 Cu1 N3 C5 129(7) . . . . ?
N1 Cu1 N3 C5 -110(7) . . . . ?
N4 Cu1 N3 C5 4(7) . . . . ?
N2 Cu1 N4 C7 140(6) . . . . ?
N3 Cu1 N4 C7 -96(6) . . . . ?
N1 Cu1 N4 C7 21(7) . . . . ?
N7 Cu2 N5 C9 -137(7) . . . . ?
N8 Cu2 N5 C9 -19(7) . . . . ?
N6 Cu2 N5 C9 98(7) . . . . ?
N7 Cu2 N6 C11 99(7) . . . . ?
N5 Cu2 N6 C11 -137(7) . . . . ?
N8 Cu2 N6 C11 -21(7) . . . . ?
N5 Cu2 N7 C13 70(21) . . . . ?
N8 Cu2 N7 C13 -47(21) . . . . ?
N6 Cu2 N7 C13 -167(21) . . . . ?
N7 Cu2 N8 C15 147(8) . . . . ?
N5 Cu2 N8 C15 27(8) . . . . ?
N6 Cu2 N8 C15 -91(8) . . . . ?
N11 Cu3 N9 C17 18(19) . . . . ?
N12 Cu3 N9 C17 136(19) . . . . ?
N10 Cu3 N9 C17 -103(19) . . . . ?
N11 Cu3 N10 C19 -124(6) . . . . ?
N12 Cu3 N10 C19 109(6) . . . . ?
N9 Cu3 N10 C19 -8(6) . . . . ?
N12 Cu3 N11 C21 -106(4) . . . . ?
N10 Cu3 N11 C21 127(4) . . . . ?
N9 Cu3 N11 C21 9(4) . . . . ?
N11 Cu3 N12 C23 99(7) . . . . ?
N10 Cu3 N12 C23 -134(7) . . . . ?
N9 Cu3 N12 C23 -16(7) . . . . ?
Cu1 N1 C1 C2 -144(14) . . . . ?
Cu1 N2 C3 C4 19(75) . . . . ?
Cu1 N3 C5 C6 -151(27) . . . . ?
Cu1 N4 C7 C8 -86(13) . . . . ?
Cu2 N5 C9 C10 -79(67) . . . . ?
Cu2 N6 C11 C12 129(13) . . . . ?
Cu2 N7 C13 C14 149(15) . . . . ?
Cu2 N8 C15 C16 -60(39) . . . . ?
Cu3 N9 C17 C18 167(13) . . . . ?
Cu3 N10 C19 C20 -79(33) . . . . ?
Cu3 N11 C21 C22 -110(14) . . . . ?
Cu3 N12 C23 C24 116(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         1.746
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_cd15336
_database_code_depnum_ccdc_archive 'CCDC 1444005'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 N3 O4 S2'
_chemical_formula_weight         599.74

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                   33.342(3)
_cell_length_b                   14.1163(13)
_cell_length_c                   13.8882(14)
_cell_angle_alpha                90
_cell_angle_beta                 113.533(2)
_cell_angle_gamma                90
_cell_volume                     5993.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3125
_cell_measurement_theta_min      4.872
_cell_measurement_theta_max      42.765

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6597
_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            17770
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.589
_diffrn_reflns_theta_max         25.999
_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             5909
_reflns_number_gt                4034
_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)+(0.0766P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.015
_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 0.08849(2) 0.09400(4) 0.13839(5) 0.0618(2) Uani 1 1 d . . . . .
S2 S 0.19824(2) 0.07931(4) 0.49756(5) 0.05228(19) Uani 1 1 d . . . . .
N1 N 0.05561(6) 0.19900(13) 0.34629(15) 0.0535(5) Uani 1 1 d . . . . .
N2 N 0.09404(6) 0.16483(12) 0.23596(14) 0.0499(5) Uani 1 1 d . . . . .
N3 N 0.15095(6) 0.13214(12) 0.44002(14) 0.0520(5) Uani 1 1 d . . . . .
O1 O 0.04836(7) 0.11425(13) 0.05149(13) 0.0836(6) Uani 1 1 d . . . . .
O2 O 0.12855(7) 0.09756(13) 0.12453(16) 0.0852(6) Uani 1 1 d . . . . .
O3 O 0.22328(5) 0.10561(11) 0.43891(13) 0.0615(4) Uani 1 1 d . . . . .
O4 O 0.18986(5) -0.01825(10) 0.50781(13) 0.0656(5) Uani 1 1 d . . . . .
C1 C 0.05454(7) 0.28674(18) 0.3907(2) 0.0576(6) Uani 1 1 d . . . . .
C2 C 0.05020(9) 0.3064(2) 0.4833(2) 0.0764(8) Uani 1 1 d . . . . .
H2 H 0.0498 0.2581 0.5284 0.092 Uiso 1 1 calc R U . . .
C3 C 0.04652(11) 0.4002(3) 0.5071(3) 0.0983(11) Uani 1 1 d . . . . .
H3 H 0.0437 0.4148 0.5693 0.118 Uiso 1 1 calc R U . . .
C4 C 0.04695(11) 0.4721(3) 0.4417(3) 0.1004(11) Uani 1 1 d . . . . .
H4 H 0.0436 0.5344 0.4587 0.120 Uiso 1 1 calc R U . . .
C5 C 0.05242(9) 0.4523(2) 0.3505(3) 0.0783(8) Uani 1 1 d . . . . .
H5 H 0.0530 0.5011 0.3061 0.094 Uiso 1 1 calc R U . . .
C6 C 0.05704(7) 0.35982(18) 0.3257(2) 0.0584(6) Uani 1 1 d . . . . .
C7 C 0.06258(7) 0.31894(16) 0.23200(18) 0.0537(6) Uani 1 1 d . . . . .
H7 H 0.0399 0.3433 0.1669 0.064 Uiso 1 1 calc R U . . .
C8 C 0.10866(7) 0.32507(15) 0.22718(18) 0.0495(5) Uani 1 1 d . . . . .
H8 H 0.1027 0.3182 0.1525 0.059 Uiso 1 1 calc R U . . .
C9 C 0.13098(7) 0.23101(14) 0.27773(17) 0.0463(5) Uani 1 1 d . . . . .
H9 H 0.1532 0.2141 0.2512 0.056 Uiso 1 1 calc R U . . .
C10 C 0.05629(7) 0.21107(16) 0.24253(18) 0.0530(6) Uani 1 1 d . . . . .
H10 H 0.0290 0.1886 0.1872 0.064 Uiso 1 1 calc R U . . .
C11 C 0.15107(7) 0.22850(14) 0.39838(17) 0.0478(5) Uani 1 1 d . . . . .
H11A H 0.1809 0.2515 0.4239 0.057 Uiso 1 1 calc R U . . .
H11B H 0.1347 0.2706 0.4245 0.057 Uiso 1 1 calc R U . . .
C12 C 0.11888(8) 0.11583(17) 0.48650(19) 0.0587(6) Uani 1 1 d . . . . .
H12A H 0.1220 0.1656 0.5372 0.070 Uiso 1 1 calc R U . . .
H12B H 0.1256 0.0561 0.5242 0.070 Uiso 1 1 calc R U . . .
C13 C 0.07158(8) 0.11336(17) 0.40719(19) 0.0594(6) Uani 1 1 d . . . . .
H13A H 0.0684 0.0614 0.3590 0.071 Uiso 1 1 calc R U . . .
H13B H 0.0531 0.0996 0.4445 0.071 Uiso 1 1 calc R U . . .
C14 C 0.13447(7) 0.41575(15) 0.2598(2) 0.0549(6) Uani 1 1 d . . . . .
C15 C 0.15202(10) 0.45093(18) 0.3610(2) 0.0786(8) Uani 1 1 d . . . . .
H15 H 0.1475 0.4185 0.4141 0.094 Uiso 1 1 calc R U . . .
C16 C 0.17621(11) 0.5335(2) 0.3845(3) 0.0973(11) Uani 1 1 d . . . . .
H16 H 0.1883 0.5552 0.4534 0.117 Uiso 1 1 calc R U . . .
C17 C 0.18258(13) 0.5829(2) 0.3093(4) 0.1122(13) Uani 1 1 d . . . . .
H17 H 0.1983 0.6392 0.3258 0.135 Uiso 1 1 calc R U . . .
C18 C 0.16595(15) 0.5502(3) 0.2091(4) 0.1234(14) Uani 1 1 d . . . . .
H18 H 0.1705 0.5837 0.1566 0.148 Uiso 1 1 calc R U . . .
C19 C 0.14221(11) 0.4668(2) 0.1854(3) 0.0881(9) Uani 1 1 d . . . . .
H19 H 0.1312 0.4447 0.1166 0.106 Uiso 1 1 calc R U . . .
C20 C 0.08334(8) -0.01798(16) 0.18648(18) 0.0565(6) Uani 1 1 d . . . . .
C21 C 0.12015(9) -0.0605(2) 0.2610(2) 0.0740(8) Uani 1 1 d . . . . .
H21 H 0.1473 -0.0309 0.2835 0.089 Uiso 1 1 calc R U . . .
C22 C 0.11591(11) -0.1464(2) 0.3006(3) 0.0899(10) Uani 1 1 d . . . . .
H22 H 0.1406 -0.1748 0.3508 0.108 Uiso 1 1 calc R U . . .
C23 C 0.07608(11) -0.1928(2) 0.2685(3) 0.0845(9) Uani 1 1 d . . . . .
C24 C 0.04035(10) -0.1499(2) 0.1935(2) 0.0774(8) Uani 1 1 d . . . . .
H24 H 0.0134 -0.1803 0.1699 0.093 Uiso 1 1 calc R U . . .
C25 C 0.04340(9) -0.06264(18) 0.1521(2) 0.0628(7) Uani 1 1 d . . . . .
H25 H 0.0188 -0.0344 0.1016 0.075 Uiso 1 1 calc R U . . .
C26 C 0.07220(15) -0.2871(3) 0.3154(4) 0.1405(17) Uani 1 1 d . . . . .
H26A H 0.0425 -0.3090 0.2833 0.211 Uiso 1 1 calc R U . . .
H26B H 0.0805 -0.2800 0.3896 0.211 Uiso 1 1 calc R U . . .
H26C H 0.0911 -0.3323 0.3031 0.211 Uiso 1 1 calc R U . . .
C27 C 0.22345(7) 0.12713(15) 0.62466(18) 0.0503(5) Uani 1 1 d . . . . .
C28 C 0.22473(9) 0.07718(18) 0.7116(2) 0.0700(8) Uani 1 1 d . . . . .
H28 H 0.2117 0.0178 0.7035 0.084 Uiso 1 1 calc R U . . .
C29 C 0.24544(10) 0.1160(2) 0.8100(2) 0.0780(8) Uani 1 1 d . . . . .
H29 H 0.2464 0.0818 0.8682 0.094 Uiso 1 1 calc R U . . .
C30 C 0.26490(8) 0.20460(18) 0.8249(2) 0.0648(7) Uani 1 1 d . . . . .
C31 C 0.26159(8) 0.25463(16) 0.7371(2) 0.0579(6) Uani 1 1 d . . . . .
H31 H 0.2731 0.3155 0.7449 0.070 Uiso 1 1 calc R U . . .
C32 C 0.24159(7) 0.21680(16) 0.6379(2) 0.0555(6) Uani 1 1 d . . . . .
H32 H 0.2403 0.2515 0.5798 0.067 Uiso 1 1 calc R U . . .
C33 C 0.28997(12) 0.2452(2) 0.9321(2) 0.0953(10) Uani 1 1 d . . . . .
H33A H 0.3206 0.2327 0.9530 0.143 Uiso 1 1 calc R U . . .
H33B H 0.2801 0.2166 0.9814 0.143 Uiso 1 1 calc R U . . .
H33C H 0.2853 0.3124 0.9305 0.143 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 1.424(2) . ?
S1 O1 1.428(2) . ?
S1 N2 1.6339(19) . ?
S1 C20 1.751(2) . ?
S2 O4 1.4237(16) . ?
S2 O3 1.4285(17) . ?
S2 N3 1.6356(19) . ?
S2 C27 1.759(2) . ?
N1 C1 1.391(3) . ?
N1 C13 1.449(3) . ?
N1 C10 1.460(3) . ?
N2 C10 1.453(3) . ?
N2 C9 1.468(3) . ?
N3 C12 1.471(3) . ?
N3 C11 1.479(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.395(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C10 1.552(3) . ?
C7 C8 1.567(3) . ?
C7 H7 0.9800 . ?
C8 C14 1.508(3) . ?
C8 C9 1.547(3) . ?
C8 H8 0.9800 . ?
C9 C11 1.537(3) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.366(4) . ?
C14 C15 1.381(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.340(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.357(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.375(3) . ?
C20 C21 1.387(3) . ?
C21 C22 1.362(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(4) . ?
C23 C26 1.510(4) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C32 1.383(3) . ?
C27 C28 1.384(3) . ?
C28 C29 1.375(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(3) . ?
C30 C33 1.500(4) . ?
C31 C32 1.376(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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 119.43(13) . . ?
O2 S1 N2 106.78(10) . . ?
O1 S1 N2 109.64(11) . . ?
O2 S1 C20 108.88(12) . . ?
O1 S1 C20 107.55(12) . . ?
N2 S1 C20 103.41(10) . . ?
O4 S2 O3 119.42(10) . . ?
O4 S2 N3 107.47(10) . . ?
O3 S2 N3 105.77(10) . . ?
O4 S2 C27 107.76(10) . . ?
O3 S2 C27 108.58(11) . . ?
N3 S2 C27 107.25(10) . . ?
C1 N1 C13 123.5(2) . . ?
C1 N1 C10 110.31(19) . . ?
C13 N1 C10 121.76(19) . . ?
C10 N2 C9 107.48(17) . . ?
C10 N2 S1 120.86(14) . . ?
C9 N2 S1 121.10(15) . . ?
C12 N3 C11 115.56(18) . . ?
C12 N3 S2 116.24(14) . . ?
C11 N3 S2 117.25(14) . . ?
C2 C1 N1 128.6(3) . . ?
C2 C1 C6 120.7(3) . . ?
N1 C1 C6 110.6(2) . . ?
C1 C2 C3 117.9(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 C7 130.4(3) . . ?
C1 C6 C7 109.7(2) . . ?
C6 C7 C10 103.15(19) . . ?
C6 C7 C8 118.56(19) . . ?
C10 C7 C8 103.30(17) . . ?
C6 C7 H7 110.4 . . ?
C10 C7 H7 110.4 . . ?
C8 C7 H7 110.4 . . ?
C14 C8 C9 118.62(18) . . ?
C14 C8 C7 119.06(19) . . ?
C9 C8 C7 103.62(17) . . ?
C14 C8 H8 104.6 . . ?
C9 C8 H8 104.6 . . ?
C7 C8 H8 104.6 . . ?
N2 C9 C11 110.35(17) . . ?
N2 C9 C8 101.03(16) . . ?
C11 C9 C8 115.85(18) . . ?
N2 C9 H9 109.7 . . ?
C11 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
N2 C10 N1 111.39(18) . . ?
N2 C10 C7 106.36(17) . . ?
N1 C10 C7 105.27(18) . . ?
N2 C10 H10 111.2 . . ?
N1 C10 H10 111.2 . . ?
C7 C10 H10 111.2 . . ?
N3 C11 C9 112.31(17) . . ?
N3 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C13 114.25(19) . . ?
N3 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N1 C13 C12 115.88(19) . . ?
N1 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
N1 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C19 C14 C15 116.7(2) . . ?
C19 C14 C8 118.5(2) . . ?
C15 C14 C8 124.8(2) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 122.2(3) . . ?
C14 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C25 C20 C21 120.4(2) . . ?
C25 C20 S1 120.68(19) . . ?
C21 C20 S1 118.9(2) . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 122.2(3) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C22 117.7(3) . . ?
C24 C23 C26 121.3(3) . . ?
C22 C23 C26 121.0(3) . . ?
C23 C24 C25 121.7(3) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C20 C25 C24 119.1(2) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 119.4(2) . . ?
C32 C27 S2 119.52(18) . . ?
C28 C27 S2 121.06(18) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 121.8(2) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 117.7(2) . . ?
C31 C30 C33 120.0(2) . . ?
C29 C30 C33 122.3(2) . . ?
C30 C31 C32 121.6(2) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C27 120.0(2) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 152.25(18) . . . . ?
O1 S1 N2 C10 21.5(2) . . . . ?
C20 S1 N2 C10 -92.96(18) . . . . ?
O2 S1 N2 C9 12.0(2) . . . . ?
O1 S1 N2 C9 -118.76(17) . . . . ?
C20 S1 N2 C9 126.76(17) . . . . ?
O4 S2 N3 C12 51.36(19) . . . . ?
O3 S2 N3 C12 179.97(16) . . . . ?
C27 S2 N3 C12 -64.28(18) . . . . ?
O4 S2 N3 C11 -165.99(16) . . . . ?
O3 S2 N3 C11 -37.38(19) . . . . ?
C27 S2 N3 C11 78.37(18) . . . . ?
C13 N1 C1 C2 -28.9(4) . . . . ?
C10 N1 C1 C2 174.4(2) . . . . ?
C13 N1 C1 C6 153.3(2) . . . . ?
C10 N1 C1 C6 -3.5(2) . . . . ?
N1 C1 C2 C3 -174.9(2) . . . . ?
C6 C1 C2 C3 2.7(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 2.4(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C2 C1 C6 C5 -4.1(4) . . . . ?
N1 C1 C6 C5 174.0(2) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
N1 C1 C6 C7 -3.1(3) . . . . ?
C5 C6 C7 C10 -168.9(2) . . . . ?
C1 C6 C7 C10 7.9(2) . . . . ?
C5 C6 C7 C8 77.8(3) . . . . ?
C1 C6 C7 C8 -105.5(2) . . . . ?
C6 C7 C8 C14 -42.5(3) . . . . ?
C10 C7 C8 C14 -155.7(2) . . . . ?
C6 C7 C8 C9 91.8(2) . . . . ?
C10 C7 C8 C9 -21.4(2) . . . . ?
C10 N2 C9 C11 80.3(2) . . . . ?
S1 N2 C9 C11 -134.85(17) . . . . ?
C10 N2 C9 C8 -42.8(2) . . . . ?
S1 N2 C9 C8 102.05(18) . . . . ?
C14 C8 C9 N2 173.2(2) . . . . ?
C7 C8 C9 N2 38.6(2) . . . . ?
C14 C8 C9 C11 53.9(3) . . . . ?
C7 C8 C9 C11 -80.6(2) . . . . ?
C9 N2 C10 N1 -84.6(2) . . . . ?
S1 N2 C10 N1 130.46(16) . . . . ?
C9 N2 C10 C7 29.6(2) . . . . ?
S1 N2 C10 C7 -115.34(17) . . . . ?
C1 N1 C10 N2 123.17(19) . . . . ?
C13 N1 C10 N2 -34.1(3) . . . . ?
C1 N1 C10 C7 8.3(2) . . . . ?
C13 N1 C10 C7 -148.95(19) . . . . ?
C6 C7 C10 N2 -127.81(18) . . . . ?
C8 C7 C10 N2 -3.8(2) . . . . ?
C6 C7 C10 N1 -9.5(2) . . . . ?
C8 C7 C10 N1 114.54(18) . . . . ?
C12 N3 C11 C9 -106.8(2) . . . . ?
S2 N3 C11 C9 110.27(18) . . . . ?
N2 C9 C11 N3 36.7(2) . . . . ?
C8 C9 C11 N3 150.66(18) . . . . ?
C11 N3 C12 C13 70.4(3) . . . . ?
S2 N3 C12 C13 -146.28(18) . . . . ?
C1 N1 C13 C12 -59.5(3) . . . . ?
C10 N1 C13 C12 94.7(3) . . . . ?
N3 C12 C13 N1 -60.5(3) . . . . ?
C9 C8 C14 C19 118.3(3) . . . . ?
C7 C8 C14 C19 -114.1(3) . . . . ?
C9 C8 C14 C15 -60.2(3) . . . . ?
C7 C8 C14 C15 67.4(3) . . . . ?
C19 C14 C15 C16 -0.2(4) . . . . ?
C8 C14 C15 C16 178.3(3) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C16 C17 C18 C19 0.7(7) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C8 C14 C19 C18 -179.4(3) . . . . ?
C17 C18 C19 C14 0.5(6) . . . . ?
O2 S1 C20 C25 -141.2(2) . . . . ?
O1 S1 C20 C25 -10.5(2) . . . . ?
N2 S1 C20 C25 105.5(2) . . . . ?
O2 S1 C20 C21 39.6(2) . . . . ?
O1 S1 C20 C21 170.4(2) . . . . ?
N2 S1 C20 C21 -73.7(2) . . . . ?
C25 C20 C21 C22 -1.0(4) . . . . ?
S1 C20 C21 C22 178.2(2) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C21 C22 C23 C26 -178.8(4) . . . . ?
C22 C23 C24 C25 -1.1(5) . . . . ?
C26 C23 C24 C25 178.4(3) . . . . ?
C21 C20 C25 C24 0.7(4) . . . . ?
S1 C20 C25 C24 -178.5(2) . . . . ?
C23 C24 C25 C20 0.4(4) . . . . ?
O4 S2 C27 C32 169.43(18) . . . . ?
O3 S2 C27 C32 38.7(2) . . . . ?
N3 S2 C27 C32 -75.1(2) . . . . ?
O4 S2 C27 C28 -11.8(2) . . . . ?
O3 S2 C27 C28 -142.5(2) . . . . ?
N3 S2 C27 C28 103.7(2) . . . . ?
C32 C27 C28 C29 -2.5(4) . . . . ?
S2 C27 C28 C29 178.8(2) . . . . ?
C27 C28 C29 C30 0.6(5) . . . . ?
C28 C29 C30 C31 2.2(4) . . . . ?
C28 C29 C30 C33 -176.2(3) . . . . ?
C29 C30 C31 C32 -3.1(4) . . . . ?
C33 C30 C31 C32 175.3(3) . . . . ?
C30 C31 C32 C27 1.3(4) . . . . ?
C28 C27 C32 C31 1.5(4) . . . . ?
S2 C27 C32 C31 -179.65(18) . . . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.052

_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_cd15264
_database_code_depnum_ccdc_archive 'CCDC 1437967'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2017-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H33 N3 O4 S2'
_chemical_formula_weight         599.74

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                   20.618(2)
_cell_length_b                   12.7286(14)
_cell_length_c                   11.5829(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.577(2)
_cell_angle_gamma                90
_cell_volume                     3019.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5273
_cell_measurement_theta_min      4.772
_cell_measurement_theta_max      48.968

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6698
_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            17809
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.884
_diffrn_reflns_theta_max         25.999
_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             5949
_reflns_number_gt                4672
_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)+(0.0669P)²+0.4830P] 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         5949
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.014
_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 0.25334(3) 0.66966(4) 0.28150(4) 0.04951(15) Uani 1 1 d . . . . .
S2 S 0.36930(2) 0.40961(4) 0.08326(5) 0.05486(16) Uani 1 1 d . . . . .
N1 N 0.09146(7) 0.55210(12) -0.00991(14) 0.0484(4) Uani 1 1 d . . . . .
N2 N 0.20533(7) 0.62220(11) 0.17046(13) 0.0448(4) Uani 1 1 d . . . . .
N3 N 0.29693(8) 0.43523(13) 0.12045(16) 0.0441(4) Uani 1 1 d . . . . .
O1 O 0.21375(8) 0.68446(11) 0.37310(12) 0.0662(4) Uani 1 1 d . . . . .
O2 O 0.30837(8) 0.60106(11) 0.29742(12) 0.0630(4) Uani 1 1 d . . . . .
O3 O 0.35922(7) 0.36730(13) -0.03142(15) 0.0726(5) Uani 1 1 d . . . . .
O4 O 0.40142(8) 0.35026(12) 0.17652(17) 0.0807(5) Uani 1 1 d . . . . .
C1 C 0.05385(9) 0.59132(16) -0.10589(19) 0.0535(5) Uani 1 1 d . . . . .
C2 C 0.01085(11) 0.6761(2) -0.1162(3) 0.0778(7) Uani 1 1 d . . . . .
H2 H 0.0028 0.7156 -0.0518 0.093 Uiso 1 1 calc R U . . .
C3 C -0.01924(12) 0.6989(3) -0.2256(3) 0.0972(10) Uani 1 1 d . . . . .
H3 H -0.0475 0.7560 -0.2352 0.117 Uiso 1 1 calc R U . . .
C4 C -0.00865(12) 0.6395(3) -0.3212(3) 0.0951(10) Uani 1 1 d . . . . .
H4 H -0.0303 0.6565 -0.3937 0.114 Uiso 1 1 calc R U . . .
C5 C 0.03309(11) 0.5563(2) -0.3111(2) 0.0759(7) Uani 1 1 d . . . . .
H5 H 0.0397 0.5164 -0.3760 0.091 Uiso 1 1 calc R U . . .
C6 C 0.06583(9) 0.53144(16) -0.20269(18) 0.0531(5) Uani 1 1 d . . . . .
C7 C 0.11321(9) 0.45489(15) -0.16053(16) 0.0470(4) Uani 1 1 d . . . . .
H7 H 0.1305 0.4033 -0.2049 0.056 Uiso 1 1 calc R U . . .
C8 C 0.12873(8) 0.46999(13) -0.04485(16) 0.0400(4) Uani 1 1 d . . . . .
C9 C 0.18177(8) 0.41916(12) 0.03621(15) 0.0381(4) Uani 1 1 d . . . . .
H9 H 0.1682 0.4200 0.1145 0.046 Uiso 1 1 calc R U . . .
C10 C 0.24601(8) 0.48360(12) 0.03901(15) 0.0373(4) Uani 1 1 d . . . . .
H10 H 0.2604 0.4787 -0.0386 0.045 Uiso 1 1 calc R U . . .
C11 C 0.23689(9) 0.60038(12) 0.06438(15) 0.0403(4) Uani 1 1 d . . . . .
H11A H 0.2793 0.6342 0.0719 0.048 Uiso 1 1 calc R U . . .
H11B H 0.2107 0.6318 -0.0016 0.048 Uiso 1 1 calc R U . . .
C12 C 0.13925(10) 0.66851(15) 0.15094(19) 0.0545(5) Uani 1 1 d . . . . .
H12A H 0.1390 0.7244 0.0940 0.065 Uiso 1 1 calc R U . . .
H12B H 0.1283 0.6990 0.2230 0.065 Uiso 1 1 calc R U . . .
C13 C 0.08833(9) 0.58810(16) 0.10874(18) 0.0534(5) Uani 1 1 d . . . . .
H13A H 0.0931 0.5278 0.1603 0.064 Uiso 1 1 calc R U . . .
H13B H 0.0455 0.6180 0.1138 0.064 Uiso 1 1 calc R U . . .
C14 C 0.18921(8) 0.30534(13) 0.00101(15) 0.0413(4) Uani 1 1 d . . . . .
C15 C 0.15857(9) 0.22745(14) 0.05786(18) 0.0508(5) Uani 1 1 d . . . . .
H15 H 0.1370 0.2449 0.1214 0.061 Uiso 1 1 calc R U . . .
C16 C 0.15956(12) 0.12440(16) 0.0217(2) 0.0672(6) Uani 1 1 d . . . . .
H16 H 0.1383 0.0733 0.0607 0.081 Uiso 1 1 calc R U . . .
C17 C 0.19115(14) 0.09677(18) -0.0701(3) 0.0776(7) Uani 1 1 d . . . . .
H17 H 0.1915 0.0271 -0.0942 0.093 Uiso 1 1 calc R U . . .
C18 C 0.22252(13) 0.17229(18) -0.1268(2) 0.0713(7) Uani 1 1 d . . . . .
H18 H 0.2445 0.1536 -0.1896 0.086 Uiso 1 1 calc R U . . .
C19 C 0.22182(10) 0.27625(16) -0.09172(18) 0.0550(5) Uani 1 1 d . . . . .
H19 H 0.2434 0.3268 -0.1308 0.066 Uiso 1 1 calc R U . . .
C20 C 0.28035(9) 0.79250(14) 0.23828(16) 0.0450(4) Uani 1 1 d . . . . .
C21 C 0.33866(10) 0.80210(16) 0.1911(2) 0.0593(5) Uani 1 1 d . . . . .
H21 H 0.3646 0.7433 0.1834 0.071 Uiso 1 1 calc R U . . .
C22 C 0.35803(11) 0.89833(19) 0.1559(2) 0.0693(6) Uani 1 1 d . . . . .
H22 H 0.3974 0.9041 0.1243 0.083 Uiso 1 1 calc R U . . .
C23 C 0.32072(11) 0.98739(17) 0.1659(2) 0.0609(5) Uani 1 1 d . . . . .
C24 C 0.26253(10) 0.97574(15) 0.21148(18) 0.0552(5) Uani 1 1 d . . . . .
H24 H 0.2365 1.0346 0.2183 0.066 Uiso 1 1 calc R U . . .
C25 C 0.24153(9) 0.88021(14) 0.24724(16) 0.0475(4) Uani 1 1 d . . . . .
H25 H 0.2017 0.8744 0.2772 0.057 Uiso 1 1 calc R U . . .
C26 C 0.34346(15) 1.0938(2) 0.1310(3) 0.0997(10) Uani 1 1 d . . . . .
H26A H 0.3106 1.1452 0.1415 0.149 Uiso 1 1 calc R U . . .
H26B H 0.3512 1.0922 0.0509 0.149 Uiso 1 1 calc R U . . .
H26C H 0.3832 1.1118 0.1785 0.149 Uiso 1 1 calc R U . . .
C27 C 0.41283(9) 0.52802(16) 0.07495(18) 0.0503(5) Uani 1 1 d . . . . .
C28 C 0.45350(10) 0.56481(18) 0.1694(2) 0.0624(5) Uani 1 1 d . . . . .
H28 H 0.4575 0.5280 0.2392 0.075 Uiso 1 1 calc R U . . .
C29 C 0.48806(10) 0.65649(18) 0.1595(2) 0.0643(6) Uani 1 1 d . . . . .
H29 H 0.5156 0.6806 0.2232 0.077 Uiso 1 1 calc R U . . .
C30 C 0.48289(9) 0.71284(17) 0.0584(2) 0.0590(5) Uani 1 1 d . . . . .
C31 C 0.44176(12) 0.6752(2) -0.0342(2) 0.0756(7) Uani 1 1 d . . . . .
H31 H 0.4371 0.7127 -0.1036 0.091 Uiso 1 1 calc R U . . .
C32 C 0.40732(11) 0.5835(2) -0.0267(2) 0.0680(6) Uani 1 1 d . . . . .
H32 H 0.3802 0.5592 -0.0909 0.082 Uiso 1 1 calc R U . . .
C33 C 0.52141(12) 0.81233(19) 0.0480(3) 0.0793(7) Uani 1 1 d . . . . .
H33A H 0.5251 0.8494 0.1206 0.119 Uiso 1 1 calc R U . . .
H33B H 0.4995 0.8558 -0.0119 0.119 Uiso 1 1 calc R U . . .
H33C H 0.5642 0.7951 0.0288 0.119 Uiso 1 1 calc R U . . .
H3A H 0.2994(10) 0.4581(16) 0.1792(18) 0.046(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4233(15) . ?
S1 O2 1.4268(15) . ?
S1 N2 1.6454(16) . ?
S1 C20 1.7519(19) . ?
S2 O4 1.4185(17) . ?
S2 O3 1.4264(17) . ?
S2 N3 1.6326(17) . ?
S2 C27 1.762(2) . ?
N1 C1 1.374(3) . ?
N1 C8 1.385(2) . ?
N1 C13 1.457(2) . ?
N2 C12 1.478(2) . ?
N2 C11 1.481(2) . ?
N3 C10 1.464(2) . ?
N3 H3A 0.74(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.426(3) . ?
C7 C8 1.355(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.504(2) . ?
C9 C14 1.518(2) . ?
C9 C10 1.555(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.531(2) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C19 1.381(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.382(3) . ?
C20 C25 1.384(3) . ?
C21 C22 1.365(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 C26 1.503(3) . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C32 1.367(3) . ?
C27 C28 1.382(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(3) . ?
C30 C33 1.507(3) . ?
C31 C32 1.374(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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 120.00(9) . . ?
O1 S1 N2 106.63(9) . . ?
O2 S1 N2 105.94(8) . . ?
O1 S1 C20 108.85(8) . . ?
O2 S1 C20 108.01(9) . . ?
N2 S1 C20 106.66(8) . . ?
O4 S2 O3 120.91(11) . . ?
O4 S2 N3 105.45(10) . . ?
O3 S2 N3 106.32(9) . . ?
O4 S2 C27 107.50(10) . . ?
O3 S2 C27 107.03(10) . . ?
N3 S2 C27 109.28(8) . . ?
C1 N1 C8 108.56(16) . . ?
C1 N1 C13 124.53(16) . . ?
C8 N1 C13 126.80(16) . . ?
C12 N2 C11 115.64(15) . . ?
C12 N2 S1 115.76(12) . . ?
C11 N2 S1 115.80(12) . . ?
C10 N3 S2 121.57(13) . . ?
C10 N3 H3A 113.4(16) . . ?
S2 N3 H3A 110.7(16) . . ?
N1 C1 C2 130.2(2) . . ?
N1 C1 C6 108.36(17) . . ?
C2 C1 C6 121.4(2) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 134.9(2) . . ?
C1 C6 C7 105.92(17) . . ?
C8 C7 C6 108.46(17) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 N1 108.66(16) . . ?
C7 C8 C9 128.96(16) . . ?
N1 C8 C9 122.04(16) . . ?
C8 C9 C14 109.37(14) . . ?
C8 C9 C10 110.05(13) . . ?
C14 C9 C10 113.41(13) . . ?
C8 C9 H9 107.9 . . ?
C14 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
N3 C10 C11 112.29(14) . . ?
N3 C10 C9 109.74(13) . . ?
C11 C10 C9 113.15(13) . . ?
N3 C10 H10 107.1 . . ?
C11 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
N2 C11 C10 114.62(13) . . ?
N2 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N2 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N2 C12 C13 112.00(15) . . ?
N2 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 C12 114.52(16) . . ?
N1 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C19 C14 C15 117.89(17) . . ?
C19 C14 C9 122.54(16) . . ?
C15 C14 C9 119.41(16) . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.5(2) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C25 119.66(18) . . ?
C21 C20 S1 120.75(15) . . ?
C25 C20 S1 119.53(14) . . ?
C22 C21 C20 119.68(19) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.7(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 117.57(19) . . ?
C24 C23 C26 120.9(2) . . ?
C22 C23 C26 121.5(2) . . ?
C25 C24 C23 122.15(19) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C24 C25 C20 119.17(18) . . ?
C24 C25 H25 120.4 . . ?
C20 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 119.4(2) . . ?
C32 C27 S2 119.75(16) . . ?
C28 C27 S2 120.88(17) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 121.7(2) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 117.8(2) . . ?
C29 C30 C33 121.3(2) . . ?
C31 C30 C33 121.0(2) . . ?
C32 C31 C30 121.6(2) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C27 C32 C31 120.0(2) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 N2 C12 40.06(15) . . . . ?
O2 S1 N2 C12 168.96(14) . . . . ?
C20 S1 N2 C12 -76.13(15) . . . . ?
O1 S1 N2 C11 -179.85(12) . . . . ?
O2 S1 N2 C11 -50.95(14) . . . . ?
C20 S1 N2 C11 63.96(14) . . . . ?
O4 S2 N3 C10 -171.73(14) . . . . ?
O3 S2 N3 C10 -42.22(17) . . . . ?
C27 S2 N3 C10 72.98(16) . . . . ?
C8 N1 C1 C2 -177.0(2) . . . . ?
C13 N1 C1 C2 6.7(3) . . . . ?
C8 N1 C1 C6 1.8(2) . . . . ?
C13 N1 C1 C6 -174.56(17) . . . . ?
N1 C1 C2 C3 178.4(2) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
N1 C1 C6 C5 179.98(18) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
N1 C1 C6 C7 -0.7(2) . . . . ?
C2 C1 C6 C7 178.18(19) . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 N1 1.7(2) . . . . ?
C6 C7 C8 C9 -171.59(16) . . . . ?
C1 N1 C8 C7 -2.2(2) . . . . ?
C13 N1 C8 C7 174.05(17) . . . . ?
C1 N1 C8 C9 171.68(15) . . . . ?
C13 N1 C8 C9 -12.1(3) . . . . ?
C7 C8 C9 C14 -36.5(2) . . . . ?
N1 C8 C9 C14 151.01(16) . . . . ?
C7 C8 C9 C10 88.7(2) . . . . ?
N1 C8 C9 C10 -83.78(19) . . . . ?
S2 N3 C10 C11 -103.35(16) . . . . ?
S2 N3 C10 C9 129.88(13) . . . . ?
C8 C9 C10 N3 178.49(14) . . . . ?
C14 C9 C10 N3 -58.64(19) . . . . ?
C8 C9 C10 C11 52.21(18) . . . . ?
C14 C9 C10 C11 175.08(14) . . . . ?
C12 N2 C11 C10 -112.15(17) . . . . ?
S1 N2 C11 C10 107.71(15) . . . . ?
N3 C10 C11 N2 -71.79(19) . . . . ?
C9 C10 C11 N2 53.1(2) . . . . ?
C11 N2 C12 C13 76.0(2) . . . . ?
S1 N2 C12 C13 -143.88(14) . . . . ?
C1 N1 C13 C12 -96.7(2) . . . . ?
C8 N1 C13 C12 87.6(2) . . . . ?
N2 C12 C13 N1 -70.9(2) . . . . ?
C8 C9 C14 C19 78.1(2) . . . . ?
C10 C9 C14 C19 -45.2(2) . . . . ?
C8 C9 C14 C15 -97.26(19) . . . . ?
C10 C9 C14 C15 139.50(17) . . . . ?
C19 C14 C15 C16 -1.2(3) . . . . ?
C9 C14 C15 C16 174.36(18) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
C9 C14 C19 C18 -174.4(2) . . . . ?
C17 C18 C19 C14 -0.2(4) . . . . ?
O1 S1 C20 C21 151.85(16) . . . . ?
O2 S1 C20 C21 20.05(19) . . . . ?
N2 S1 C20 C21 -93.45(17) . . . . ?
O1 S1 C20 C25 -30.75(18) . . . . ?
O2 S1 C20 C25 -162.55(15) . . . . ?
N2 S1 C20 C25 83.95(16) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
S1 C20 C21 C22 178.67(18) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C21 C22 C23 C26 177.7(2) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C26 C23 C24 C25 -178.0(2) . . . . ?
C23 C24 C25 C20 0.6(3) . . . . ?
C21 C20 C25 C24 -1.5(3) . . . . ?
S1 C20 C25 C24 -178.95(15) . . . . ?
O4 S2 C27 C32 157.98(18) . . . . ?
O3 S2 C27 C32 26.7(2) . . . . ?
N3 S2 C27 C32 -88.05(19) . . . . ?
O4 S2 C27 C28 -20.9(2) . . . . ?
O3 S2 C27 C28 -152.15(17) . . . . ?
N3 S2 C27 C28 93.11(18) . . . . ?
C32 C27 C28 C29 -0.3(3) . . . . ?
S2 C27 C28 C29 178.55(16) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C28 C29 C30 C31 0.1(3) . . . . ?
C28 C29 C30 C33 -179.4(2) . . . . ?
C29 C30 C31 C32 -0.7(4) . . . . ?
C33 C30 C31 C32 178.7(2) . . . . ?
C28 C27 C32 C31 -0.3(3) . . . . ?
S2 C27 C32 C31 -179.19(19) . . . . ?
C30 C31 C32 C27 0.9(4) . . . . ?

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
N3 H3A O2 0.74(2) 2.27(2) 2.933(2) 150(2) .
C12 H12B O1 0.97 2.34 2.849(3) 112.3 .

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



