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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_170308e
_database_code_depnum_ccdc_archive 'CCDC 1583691'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 N2 O5 S'
_chemical_formula_weight         566.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4008(12)
_cell_length_b                   12.9855(13)
_cell_length_c                   13.2123(15)
_cell_angle_alpha                64.9820(10)
_cell_angle_beta                 66.8950(10)
_cell_angle_gamma                83.284(2)
_cell_volume                     1627.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    765
_cell_measurement_theta_min      2.273
_cell_measurement_theta_max      18.449

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            8378
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.1477
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5676
_reflns_number_gt                2015
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 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)+(0.0504P)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_number_reflns         5676
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1713
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1974
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3609(4) 0.8411(3) 0.1191(4) 0.0554(11) Uani 1 1 d . . .
N2 N 0.4678(4) 0.7973(4) 0.1066(4) 0.0613(12) Uani 1 1 d . . .
O1 O -0.0900(3) 1.0171(3) 0.1877(4) 0.0850(13) Uani 1 1 d . . .
O2 O 0.6428(4) 0.6071(4) -0.2266(5) 0.1265(19) Uani 1 1 d . . .
O3 O 0.1081(3) 0.6544(3) 0.3505(4) 0.0926(13) Uani 1 1 d . . .
O4 O -0.0457(3) 0.7927(3) 0.3951(3) 0.0855(12) Uani 1 1 d . . .
O5 O -0.3896(4) 0.4745(3) 0.3448(4) 0.1052(15) Uani 1 1 d . . .
S1 S 0.01365(14) 0.73143(14) 0.32321(14) 0.0693(5) Uani 1 1 d . . .
C1 C 0.0072(5) 1.0066(4) 0.2069(5) 0.0586(15) Uani 1 1 d . . .
C2 C 0.1225(4) 0.9466(4) 0.1541(4) 0.0527(14) Uani 1 1 d . . .
C3 C 0.2132(4) 0.9460(4) 0.2130(4) 0.0497(13) Uani 1 1 d . . .
C4 C 0.1593(4) 1.0167(4) 0.2805(4) 0.0494(13) Uani 1 1 d . . .
C5 C 0.0391(5) 1.0519(4) 0.2779(4) 0.0531(13) Uani 1 1 d . . .
C6 C -0.0321(5) 1.1187(5) 0.3355(5) 0.0664(16) Uani 1 1 d . . .
H6 H -0.1131 1.1382 0.3353 0.080 Uiso 1 1 calc R . .
C7 C 0.0182(5) 1.1551(5) 0.3922(5) 0.0731(17) Uani 1 1 d . . .
H7 H -0.0279 1.2014 0.4304 0.088 Uiso 1 1 calc R . .
C8 C 0.1380(5) 1.1241(5) 0.3941(5) 0.0683(16) Uani 1 1 d . . .
H8 H 0.1710 1.1502 0.4338 0.082 Uiso 1 1 calc R . .
C9 C 0.2088(5) 1.0566(4) 0.3396(4) 0.0616(15) Uani 1 1 d . . .
H9 H 0.2892 1.0371 0.3417 0.074 Uiso 1 1 calc R . .
C10 C 0.3231(4) 0.8925(4) 0.2013(4) 0.0489(13) Uani 1 1 d . . .
C11 C 0.4010(5) 0.8868(5) 0.2706(5) 0.0537(14) Uani 1 1 d . . .
C12 C 0.3614(5) 0.8113(5) 0.3901(6) 0.0698(16) Uani 1 1 d . . .
H12 H 0.2899 0.7621 0.4244 0.084 Uiso 1 1 calc R . .
C13 C 0.4284(6) 0.8083(5) 0.4604(5) 0.0783(17) Uani 1 1 d . . .
H13 H 0.3996 0.7578 0.5414 0.094 Uiso 1 1 calc R . .
C14 C 0.5350(5) 0.8779(5) 0.4124(6) 0.0683(16) Uani 1 1 d . . .
C15 C 0.5733(5) 0.9519(5) 0.2911(6) 0.0724(17) Uani 1 1 d . . .
H15 H 0.6457 1.0004 0.2552 0.087 Uiso 1 1 calc R . .
C16 C 0.5067(5) 0.9553(5) 0.2225(5) 0.0639(15) Uani 1 1 d . . .
H16 H 0.5353 1.0057 0.1415 0.077 Uiso 1 1 calc R . .
C17 C 0.6064(5) 0.8737(6) 0.4892(6) 0.107(2) Uani 1 1 d . . .
H17A H 0.5512 0.8397 0.5730 0.160 Uiso 1 1 calc R . .
H17B H 0.6339 0.9496 0.4687 0.160 Uiso 1 1 calc R . .
H17C H 0.6796 0.8292 0.4748 0.160 Uiso 1 1 calc R . .
C18 C 0.5055(5) 0.7480(4) 0.0231(4) 0.0529(14) Uani 1 1 d . . .
C19 C 0.6210(5) 0.7044(5) 0.0013(5) 0.0758(18) Uani 1 1 d . . .
H19 H 0.6694 0.7069 0.0429 0.091 Uiso 1 1 calc R . .
C20 C 0.6699(5) 0.6564(5) -0.0800(6) 0.0843(19) Uani 1 1 d . . .
H20 H 0.7510 0.6284 -0.0940 0.101 Uiso 1 1 calc R . .
C21 C 0.6009(6) 0.6493(6) -0.1403(6) 0.085(2) Uani 1 1 d . . .
C22 C 0.4849(6) 0.6930(6) -0.1195(6) 0.111(3) Uani 1 1 d . . .
H22 H 0.4366 0.6904 -0.1611 0.133 Uiso 1 1 calc R . .
C23 C 0.4369(5) 0.7411(6) -0.0379(6) 0.093(2) Uani 1 1 d . . .
H23 H 0.3560 0.7694 -0.0241 0.112 Uiso 1 1 calc R . .
C24 C 0.7594(6) 0.5560(6) -0.2480(6) 0.128(3) Uani 1 1 d . . .
H24A H 0.8260 0.6088 -0.2687 0.192 Uiso 1 1 calc R . .
H24B H 0.7774 0.5344 -0.3134 0.192 Uiso 1 1 calc R . .
H24C H 0.7551 0.4896 -0.1766 0.192 Uiso 1 1 calc R . .
C25 C 0.1817(4) 1.0231(5) 0.0157(5) 0.0721(17) Uani 1 1 d . . .
H25A H 0.2072 1.0969 0.0030 0.108 Uiso 1 1 calc R . .
H25B H 0.1194 1.0309 -0.0188 0.108 Uiso 1 1 calc R . .
H25C H 0.2548 0.9886 -0.0221 0.108 Uiso 1 1 calc R . .
C26 C 0.0765(4) 0.8320(4) 0.1724(4) 0.0581(14) Uani 1 1 d . . .
H26A H 0.1475 0.8000 0.1269 0.070 Uiso 1 1 calc R . .
H26B H 0.0114 0.8449 0.1389 0.070 Uiso 1 1 calc R . .
C27 C -0.1067(5) 0.6569(5) 0.3264(5) 0.0595(14) Uani 1 1 d . . .
C28 C -0.2092(5) 0.7121(5) 0.3040(5) 0.0666(16) Uani 1 1 d . . .
H28 H -0.2132 0.7897 0.2851 0.080 Uiso 1 1 calc R . .
C29 C -0.3057(5) 0.6554(5) 0.3088(5) 0.0710(16) Uani 1 1 d . . .
H29 H -0.3753 0.6934 0.2934 0.085 Uiso 1 1 calc R . .
C30 C -0.2979(6) 0.5389(6) 0.3374(5) 0.0747(17) Uani 1 1 d . . .
C31 C -0.1947(6) 0.4848(5) 0.3601(6) 0.088(2) Uani 1 1 d . . .
H31 H -0.1893 0.4072 0.3792 0.106 Uiso 1 1 calc R . .
C32 C -0.0999(5) 0.5439(5) 0.3550(5) 0.0738(17) Uani 1 1 d . . .
H32 H -0.0303 0.5066 0.3711 0.089 Uiso 1 1 calc R . .
C33 C -0.5080(6) 0.5208(6) 0.3382(6) 0.115(2) Uani 1 1 d . . .
H33A H -0.5499 0.5462 0.4017 0.173 Uiso 1 1 calc R . .
H33B H -0.5617 0.4633 0.3472 0.173 Uiso 1 1 calc R . .
H33C H -0.4918 0.5840 0.2614 0.173 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
N1 N2 1.264(4) . ?
N1 C10 1.412(5) . ?
N2 C18 1.404(5) . ?
O1 C1 1.212(5) . ?
O2 C21 1.367(6) . ?
O2 C24 1.395(6) . ?
O3 S1 1.428(4) . ?
O4 S1 1.415(3) . ?
O5 C30 1.363(6) . ?
O5 C33 1.432(6) . ?
S1 C27 1.747(5) . ?
S1 C26 1.757(5) . ?
C1 C5 1.464(6) . ?
C1 C2 1.523(6) . ?
C2 C3 1.517(6) . ?
C2 C26 1.525(6) . ?
C2 C25 1.561(6) . ?
C3 C10 1.345(6) . ?
C3 C4 1.464(6) . ?
C4 C9 1.398(6) . ?
C4 C5 1.403(6) . ?
C5 C6 1.378(6) . ?
C6 C7 1.347(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.482(6) . ?
C11 C16 1.348(6) . ?
C11 C12 1.376(7) . ?
C12 C13 1.403(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(7) . ?
C14 C17 1.513(7) . ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.343(6) . ?
C18 C23 1.357(7) . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.353(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.348(7) . ?
C22 C23 1.371(7) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C32 1.352(6) . ?
C27 C28 1.365(6) . ?
C28 C29 1.360(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.396(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(7) . ?
C31 C32 1.362(7) . ?
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
N2 N1 C10 113.8(4) . . ?
N1 N2 C18 113.3(4) . . ?
C21 O2 C24 119.4(5) . . ?
C30 O5 C33 120.7(5) . . ?
O4 S1 O3 118.9(3) . . ?
O4 S1 C27 107.7(2) . . ?
O3 S1 C27 108.7(3) . . ?
O4 S1 C26 106.9(2) . . ?
O3 S1 C26 110.3(2) . . ?
C27 S1 C26 103.2(2) . . ?
O1 C1 C5 127.7(5) . . ?
O1 C1 C2 124.6(5) . . ?
C5 C1 C2 107.7(4) . . ?
C3 C2 C1 104.8(4) . . ?
C3 C2 C26 117.7(4) . . ?
C1 C2 C26 108.8(4) . . ?
C3 C2 C25 110.2(4) . . ?
C1 C2 C25 106.1(4) . . ?
C26 C2 C25 108.6(4) . . ?
C10 C3 C4 127.8(4) . . ?
C10 C3 C2 125.6(4) . . ?
C4 C3 C2 106.6(4) . . ?
C9 C4 C5 117.3(4) . . ?
C9 C4 C3 131.5(4) . . ?
C5 C4 C3 111.1(4) . . ?
C6 C5 C4 122.5(5) . . ?
C6 C5 C1 128.5(5) . . ?
C4 C5 C1 109.1(4) . . ?
C7 C6 C5 118.6(5) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 120.4(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.8(5) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C3 C10 N1 116.3(4) . . ?
C3 C10 C11 122.5(4) . . ?
N1 C10 C11 121.2(4) . . ?
C16 C11 C12 118.6(5) . . ?
C16 C11 C10 122.8(5) . . ?
C12 C11 C10 118.6(5) . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 121.4(6) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 116.8(5) . . ?
C13 C14 C17 120.9(6) . . ?
C15 C14 C17 122.4(6) . . ?
C16 C15 C14 121.7(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C11 C16 C15 121.3(6) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 117.2(5) . . ?
C19 C18 N2 116.5(5) . . ?
C23 C18 N2 126.3(5) . . ?
C18 C19 C20 122.2(5) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 120.4(5) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 118.0(6) . . ?
C22 C21 O2 116.9(6) . . ?
C20 C21 O2 125.0(6) . . ?
C21 C22 C23 121.1(6) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C18 C23 C22 121.1(5) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 C26 S1 115.2(3) . . ?
C2 C26 H26A 108.5 . . ?
S1 C26 H26A 108.5 . . ?
C2 C26 H26B 108.5 . . ?
S1 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C32 C27 C28 120.3(5) . . ?
C32 C27 S1 119.8(5) . . ?
C28 C27 S1 119.9(4) . . ?
C29 C28 C27 121.0(5) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 118.6(5) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
O5 C30 C31 117.3(6) . . ?
O5 C30 C29 123.1(6) . . ?
C31 C30 C29 119.7(6) . . ?
C32 C31 C30 120.3(6) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C27 C32 C31 120.1(5) . . ?
C27 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
O5 C33 H33A 109.5 . . ?
O5 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O5 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
C10 N1 N2 C18 -179.0(4) . . . . ?
O1 C1 C2 C3 -174.9(5) . . . . ?
C5 C1 C2 C3 7.7(5) . . . . ?
O1 C1 C2 C26 -48.2(7) . . . . ?
C5 C1 C2 C26 134.4(4) . . . . ?
O1 C1 C2 C25 68.5(6) . . . . ?
C5 C1 C2 C25 -108.9(4) . . . . ?
C1 C2 C3 C10 173.7(5) . . . . ?
C26 C2 C3 C10 52.7(7) . . . . ?
C25 C2 C3 C10 -72.5(6) . . . . ?
C1 C2 C3 C4 -7.9(5) . . . . ?
C26 C2 C3 C4 -128.8(4) . . . . ?
C25 C2 C3 C4 105.9(4) . . . . ?
C10 C3 C4 C9 6.9(9) . . . . ?
C2 C3 C4 C9 -171.6(5) . . . . ?
C10 C3 C4 C5 -176.2(5) . . . . ?
C2 C3 C4 C5 5.4(5) . . . . ?
C9 C4 C5 C6 -3.0(7) . . . . ?
C3 C4 C5 C6 179.5(5) . . . . ?
C9 C4 C5 C1 177.0(4) . . . . ?
C3 C4 C5 C1 -0.5(6) . . . . ?
O1 C1 C5 C6 -2.0(9) . . . . ?
C2 C1 C5 C6 175.3(5) . . . . ?
O1 C1 C5 C4 178.0(5) . . . . ?
C2 C1 C5 C4 -4.7(6) . . . . ?
C4 C5 C6 C7 2.7(8) . . . . ?
C1 C5 C6 C7 -177.3(5) . . . . ?
C5 C6 C7 C8 -1.1(8) . . . . ?
C6 C7 C8 C9 0.0(9) . . . . ?
C7 C8 C9 C4 -0.3(8) . . . . ?
C5 C4 C9 C8 1.8(7) . . . . ?
C3 C4 C9 C8 178.6(5) . . . . ?
C4 C3 C10 N1 -172.5(4) . . . . ?
C2 C3 C10 N1 5.6(7) . . . . ?
C4 C3 C10 C11 7.6(8) . . . . ?
C2 C3 C10 C11 -174.2(5) . . . . ?
N2 N1 C10 C3 176.5(4) . . . . ?
N2 N1 C10 C11 -3.7(7) . . . . ?
C3 C10 C11 C16 -100.7(6) . . . . ?
N1 C10 C11 C16 79.5(6) . . . . ?
C3 C10 C11 C12 77.0(6) . . . . ?
N1 C10 C11 C12 -102.8(5) . . . . ?
C16 C11 C12 C13 1.5(7) . . . . ?
C10 C11 C12 C13 -176.2(5) . . . . ?
C11 C12 C13 C14 -1.2(8) . . . . ?
C12 C13 C14 C15 0.2(8) . . . . ?
C12 C13 C14 C17 -180.0(5) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C17 C14 C15 C16 -179.5(5) . . . . ?
C12 C11 C16 C15 -1.1(7) . . . . ?
C10 C11 C16 C15 176.6(5) . . . . ?
C14 C15 C16 C11 0.2(8) . . . . ?
N1 N2 C18 C19 177.1(4) . . . . ?
N1 N2 C18 C23 -2.5(8) . . . . ?
C23 C18 C19 C20 1.1(9) . . . . ?
N2 C18 C19 C20 -178.5(5) . . . . ?
C18 C19 C20 C21 -1.3(10) . . . . ?
C19 C20 C21 C22 1.4(10) . . . . ?
C19 C20 C21 O2 177.3(6) . . . . ?
C24 O2 C21 C22 -177.0(6) . . . . ?
C24 O2 C21 C20 7.1(10) . . . . ?
C20 C21 C22 C23 -1.3(11) . . . . ?
O2 C21 C22 C23 -177.5(6) . . . . ?
C19 C18 C23 C22 -0.9(10) . . . . ?
N2 C18 C23 C22 178.6(6) . . . . ?
C21 C22 C23 C18 1.1(11) . . . . ?
C3 C2 C26 S1 51.0(5) . . . . ?
C1 C2 C26 S1 -67.9(5) . . . . ?
C25 C2 C26 S1 177.0(3) . . . . ?
O4 S1 C26 C2 32.6(4) . . . . ?
O3 S1 C26 C2 -98.1(4) . . . . ?
C27 S1 C26 C2 146.0(4) . . . . ?
O4 S1 C27 C32 -128.4(5) . . . . ?
O3 S1 C27 C32 1.6(5) . . . . ?
C26 S1 C27 C32 118.7(5) . . . . ?
O4 S1 C27 C28 49.4(5) . . . . ?
O3 S1 C27 C28 179.5(4) . . . . ?
C26 S1 C27 C28 -63.4(5) . . . . ?
C32 C27 C28 C29 -0.6(8) . . . . ?
S1 C27 C28 C29 -178.4(4) . . . . ?
C27 C28 C29 C30 0.1(8) . . . . ?
C33 O5 C30 C31 171.7(6) . . . . ?
C33 O5 C30 C29 -8.0(9) . . . . ?
C28 C29 C30 O5 179.9(5) . . . . ?
C28 C29 C30 C31 0.2(9) . . . . ?
O5 C30 C31 C32 -179.7(5) . . . . ?
C29 C30 C31 C32 0.0(9) . . . . ?
C28 C27 C32 C31 0.8(9) . . . . ?
S1 C27 C32 C31 178.6(4) . . . . ?
C30 C31 C32 C27 -0.5(9) . . . . ?

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
1 0.000 0.500 0.000 283.9 5.2
_platon_squeeze_details          
;
;


_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_170804f
_database_code_depnum_ccdc_archive 'CCDC 1583692'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 Br0.50 Cl0.50 O3 S Se'
_chemical_formula_weight         614.21

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'
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'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9091(9)
_cell_length_b                   12.3360(11)
_cell_length_c                   13.1036(12)
_cell_angle_alpha                108.864(2)
_cell_angle_beta                 96.2640(10)
_cell_angle_gamma                113.226(3)
_cell_volume                     1340.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      2.734
_cell_measurement_theta_max      25.647

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             622
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4591
_exptl_absorpt_correction_T_max  0.5447
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            6824
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4663
_reflns_number_gt                3354
_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)+(0.0867P)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_number_reflns         4663
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.71009(5) 0.71242(4) 0.23444(4) 0.04651(18) Uani 1 1 d . . .
Cl1 Cl 1.5011(13) 1.1482(14) 0.4836(11) 0.088(2) Uani 0.50 1 d P A 1
Br1 Br 1.5357(5) 1.1478(6) 0.4537(5) 0.0875(9) Uani 0.50 1 d P A 2
S1 S 0.61700(12) 0.34899(10) 0.26344(9) 0.0446(3) Uani 1 1 d . . .
O1 O 0.7296(3) 0.2359(3) -0.0010(3) 0.0554(8) Uani 1 1 d . . .
O2 O 0.7081(4) 0.2819(3) 0.2521(3) 0.0611(9) Uani 1 1 d . . .
O3 O 0.4625(4) 0.2863(3) 0.2702(3) 0.0634(9) Uani 1 1 d . . .
C1 C 0.8039(4) 0.3441(4) 0.0709(3) 0.0368(9) Uani 1 1 d . . .
C2 C 0.7406(4) 0.4442(4) 0.1035(3) 0.0359(9) Uani 1 1 d . . .
C3 C 0.8806(4) 0.5698(4) 0.1874(3) 0.0341(8) Uani 1 1 d . . .
C4 C 1.0077(4) 0.5356(4) 0.2045(3) 0.0372(9) Uani 1 1 d . . .
C5 C 0.9614(4) 0.4059(4) 0.1394(3) 0.0402(9) Uani 1 1 d . . .
C6 C 1.0520(5) 0.3456(4) 0.1455(4) 0.0475(10) Uani 1 1 d . . .
H6 H 1.0171 0.2589 0.1007 0.057 Uiso 1 1 calc R . .
C7 C 1.1956(5) 0.4176(5) 0.2197(4) 0.0560(12) Uani 1 1 d . . .
H7 H 1.2597 0.3801 0.2248 0.067 Uiso 1 1 calc R . .
C8 C 1.2443(5) 0.5470(5) 0.2874(4) 0.0587(13) Uani 1 1 d . . .
H8 H 1.3404 0.5943 0.3385 0.070 Uiso 1 1 calc R . .
C9 C 1.1535(5) 0.6063(4) 0.2801(4) 0.0507(11) Uani 1 1 d . . .
H9 H 1.1888 0.6929 0.3252 0.061 Uiso 1 1 calc R . .
C10 C 0.5979(4) 0.3881(4) 0.1448(3) 0.0382(9) Uani 1 1 d . . .
H10A H 0.5217 0.3105 0.0827 0.046 Uiso 1 1 calc R . .
H10B H 0.5570 0.4495 0.1615 0.046 Uiso 1 1 calc R . .
C11 C 0.7168(5) 0.4945(4) 0.3833(3) 0.0426(10) Uani 1 1 d . . .
C12 C 0.8716(5) 0.5418(5) 0.4314(4) 0.0561(12) Uani 1 1 d . . .
H12 H 0.9244 0.4981 0.3994 0.067 Uiso 1 1 calc R . .
C13 C 0.9463(6) 0.6545(5) 0.5275(4) 0.0639(14) Uani 1 1 d . . .
H13 H 1.0499 0.6859 0.5592 0.077 Uiso 1 1 calc R . .
C14 C 0.8716(6) 0.7213(5) 0.5774(4) 0.0623(13) Uani 1 1 d . . .
C15 C 0.7157(6) 0.6719(5) 0.5271(4) 0.0594(13) Uani 1 1 d . . .
H15 H 0.6631 0.7161 0.5585 0.071 Uiso 1 1 calc R . .
C16 C 0.6394(5) 0.5601(4) 0.4329(4) 0.0493(11) Uani 1 1 d . . .
H16 H 0.5355 0.5280 0.4020 0.059 Uiso 1 1 calc R . .
C17 C 0.9514(8) 0.8448(6) 0.6813(5) 0.090(2) Uani 1 1 d . . .
H17A H 0.9212 0.9068 0.6720 0.135 Uiso 1 1 calc R . .
H17B H 1.0598 0.8779 0.6932 0.135 Uiso 1 1 calc R . .
H17C H 0.9241 0.8283 0.7447 0.135 Uiso 1 1 calc R . .
C18 C 0.6885(5) 0.4581(4) -0.0046(3) 0.0479(11) Uani 1 1 d . . .
H18A H 0.6529 0.5222 0.0125 0.072 Uiso 1 1 calc R . .
H18B H 0.6074 0.3772 -0.0575 0.072 Uiso 1 1 calc R . .
H18C H 0.7728 0.4838 -0.0363 0.072 Uiso 1 1 calc R . .
C19 C 0.8915(4) 0.6881(4) 0.2298(3) 0.0368(9) Uani 1 1 d . . .
C20 C 1.0384(4) 0.8080(4) 0.2856(3) 0.0383(9) Uani 1 1 d . A .
C21 C 1.1456(5) 0.8405(4) 0.2271(4) 0.0483(11) Uani 1 1 d . . .
H21 H 1.1209 0.7913 0.1508 0.058 Uiso 1 1 calc R . .
C22 C 1.2887(5) 0.9446(5) 0.2797(4) 0.0578(12) Uani 1 1 d . A .
H22 H 1.3587 0.9647 0.2387 0.069 Uiso 1 1 calc R . .
C23 C 1.3277(5) 1.0179(4) 0.3917(5) 0.0594(13) Uani 1 1 d . . .
C24 C 1.2224(6) 0.9915(4) 0.4510(4) 0.0606(13) Uani 1 1 d . A .
H24 H 1.2482 1.0434 0.5267 0.073 Uiso 1 1 calc R . .
C25 C 1.0752(5) 0.8866(4) 0.3988(4) 0.0496(11) Uani 1 1 d . . .
H25 H 1.0036 0.8701 0.4393 0.060 Uiso 1 1 calc R A .
C26 C 0.7289(4) 0.8206(4) 0.1542(4) 0.0425(10) Uani 1 1 d . . .
C27 C 0.8038(5) 0.8203(4) 0.0710(4) 0.0550(12) Uani 1 1 d . . .
H27 H 0.8546 0.7701 0.0549 0.066 Uiso 1 1 calc R . .
C28 C 0.8030(6) 0.8948(5) 0.0119(4) 0.0620(13) Uani 1 1 d . . .
H28 H 0.8534 0.8941 -0.0440 0.074 Uiso 1 1 calc R . .
C29 C 0.7306(7) 0.9686(5) 0.0338(6) 0.0779(18) Uani 1 1 d . . .
H29 H 0.7314 1.0181 -0.0069 0.093 Uiso 1 1 calc R . .
C30 C 0.6560(6) 0.9708(5) 0.1157(6) 0.0781(18) Uani 1 1 d . . .
H30 H 0.6060 1.0217 0.1304 0.094 Uiso 1 1 calc R . .
C31 C 0.6545(5) 0.8975(5) 0.1771(5) 0.0616(13) Uani 1 1 d . . .
H31 H 0.6043 0.8996 0.2331 0.074 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
Se1 C26 1.917(4) . ?
Se1 C19 1.939(4) . ?
Cl1 C23 1.763(15) . ?
Br1 C23 1.915(7) . ?
S1 O2 1.436(3) . ?
S1 O3 1.446(3) . ?
S1 C11 1.762(5) . ?
S1 C10 1.782(4) . ?
O1 C1 1.213(5) . ?
C1 C5 1.462(5) . ?
C1 C2 1.558(5) . ?
C2 C18 1.540(5) . ?
C2 C3 1.551(5) . ?
C2 C10 1.552(5) . ?
C3 C19 1.337(5) . ?
C3 C4 1.495(5) . ?
C4 C5 1.397(6) . ?
C4 C9 1.401(5) . ?
C5 C6 1.384(6) . ?
C6 C7 1.379(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.386(6) . ?
C11 C12 1.392(6) . ?
C12 C13 1.386(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(7) . ?
C14 C17 1.507(7) . ?
C15 C16 1.368(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.488(5) . ?
C20 C21 1.385(6) . ?
C20 C25 1.395(6) . ?
C21 C22 1.383(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(7) . ?
C24 C25 1.411(6) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.385(6) . ?
C26 C31 1.395(6) . ?
C27 C28 1.383(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.348(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.388(8) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 Se1 C19 102.34(17) . . ?
O2 S1 O3 119.6(2) . . ?
O2 S1 C11 107.9(2) . . ?
O3 S1 C11 107.89(19) . . ?
O2 S1 C10 108.59(19) . . ?
O3 S1 C10 104.57(19) . . ?
C11 S1 C10 107.78(19) . . ?
O1 C1 C5 129.1(4) . . ?
O1 C1 C2 123.0(4) . . ?
C5 C1 C2 107.9(3) . . ?
C18 C2 C3 111.1(3) . . ?
C18 C2 C10 108.0(3) . . ?
C3 C2 C10 118.1(3) . . ?
C18 C2 C1 106.8(3) . . ?
C3 C2 C1 103.8(3) . . ?
C10 C2 C1 108.4(3) . . ?
C19 C3 C4 125.9(3) . . ?
C19 C3 C2 127.5(3) . . ?
C4 C3 C2 106.4(3) . . ?
C5 C4 C9 117.3(4) . . ?
C5 C4 C3 111.1(3) . . ?
C9 C4 C3 131.2(4) . . ?
C6 C5 C4 123.5(4) . . ?
C6 C5 C1 126.0(4) . . ?
C4 C5 C1 110.5(3) . . ?
C7 C6 C5 118.1(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 119.7(4) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C2 C10 S1 119.2(3) . . ?
C2 C10 H10A 107.5 . . ?
S1 C10 H10A 107.5 . . ?
C2 C10 H10B 107.5 . . ?
S1 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C16 C11 C12 119.5(4) . . ?
C16 C11 S1 119.8(3) . . ?
C12 C11 S1 120.6(3) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 121.8(5) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 117.7(5) . . ?
C13 C14 C17 122.5(5) . . ?
C15 C14 C17 119.8(5) . . ?
C16 C15 C14 121.4(5) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C19 C20 124.0(3) . . ?
C3 C19 Se1 120.8(3) . . ?
C20 C19 Se1 115.0(3) . . ?
C21 C20 C25 118.4(4) . . ?
C21 C20 C19 120.3(4) . . ?
C25 C20 C19 121.2(4) . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 120.3(5) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.7(4) . . ?
C22 C23 Cl1 131.3(5) . . ?
C24 C23 Cl1 109.0(5) . . ?
C22 C23 Br1 114.8(4) . . ?
C24 C23 Br1 125.4(4) . . ?
Cl1 C23 Br1 16.5(4) . . ?
C23 C24 C25 120.9(4) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C24 119.1(4) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C27 C26 C31 118.9(4) . . ?
C27 C26 Se1 123.5(3) . . ?
C31 C26 Se1 117.5(4) . . ?
C28 C27 C26 119.8(4) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C29 C28 C27 121.2(5) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.2(5) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C31 120.3(5) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 119.6(5) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C18 -56.4(5) . . . . ?
C5 C1 C2 C18 122.6(3) . . . . ?
O1 C1 C2 C3 -173.9(4) . . . . ?
C5 C1 C2 C3 5.1(4) . . . . ?
O1 C1 C2 C10 59.7(5) . . . . ?
C5 C1 C2 C10 -121.3(3) . . . . ?
C18 C2 C3 C19 56.7(5) . . . . ?
C10 C2 C3 C19 -68.8(5) . . . . ?
C1 C2 C3 C19 171.2(4) . . . . ?
C18 C2 C3 C4 -118.3(3) . . . . ?
C10 C2 C3 C4 116.2(4) . . . . ?
C1 C2 C3 C4 -3.8(4) . . . . ?
C19 C3 C4 C5 -173.9(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C19 C3 C4 C9 13.2(7) . . . . ?
C2 C3 C4 C9 -171.7(4) . . . . ?
C9 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C5 C6 -174.6(4) . . . . ?
C9 C4 C5 C1 176.2(4) . . . . ?
C3 C4 C5 C1 2.1(5) . . . . ?
O1 C1 C5 C6 -9.1(7) . . . . ?
C2 C1 C5 C6 172.0(4) . . . . ?
O1 C1 C5 C4 174.3(4) . . . . ?
C2 C1 C5 C4 -4.6(4) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C1 C5 C6 C7 -176.3(4) . . . . ?
C5 C6 C7 C8 1.1(7) . . . . ?
C6 C7 C8 C9 -1.6(8) . . . . ?
C7 C8 C9 C4 0.9(7) . . . . ?
C5 C4 C9 C8 0.1(6) . . . . ?
C3 C4 C9 C8 172.7(5) . . . . ?
C18 C2 C10 S1 175.4(3) . . . . ?
C3 C2 C10 S1 -57.5(4) . . . . ?
C1 C2 C10 S1 60.1(4) . . . . ?
O2 S1 C10 C2 -44.7(4) . . . . ?
O3 S1 C10 C2 -173.4(3) . . . . ?
C11 S1 C10 C2 71.9(3) . . . . ?
O2 S1 C11 C16 -161.3(3) . . . . ?
O3 S1 C11 C16 -30.8(4) . . . . ?
C10 S1 C11 C16 81.6(4) . . . . ?
O2 S1 C11 C12 16.2(4) . . . . ?
O3 S1 C11 C12 146.7(3) . . . . ?
C10 S1 C11 C12 -100.9(4) . . . . ?
C16 C11 C12 C13 -0.7(7) . . . . ?
S1 C11 C12 C13 -178.2(4) . . . . ?
C11 C12 C13 C14 0.3(7) . . . . ?
C12 C13 C14 C15 -0.4(7) . . . . ?
C12 C13 C14 C17 -179.4(5) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C17 C14 C15 C16 -180.0(5) . . . . ?
C14 C15 C16 C11 -1.5(7) . . . . ?
C12 C11 C16 C15 1.3(6) . . . . ?
S1 C11 C16 C15 178.8(3) . . . . ?
C4 C3 C19 C20 10.6(6) . . . . ?
C2 C3 C19 C20 -163.5(4) . . . . ?
C4 C3 C19 Se1 -163.4(3) . . . . ?
C2 C3 C19 Se1 22.5(5) . . . . ?
C26 Se1 C19 C3 -123.8(3) . . . . ?
C26 Se1 C19 C20 61.7(3) . . . . ?
C3 C19 C20 C21 61.0(5) . . . . ?
Se1 C19 C20 C21 -124.7(3) . . . . ?
C3 C19 C20 C25 -115.7(5) . . . . ?
Se1 C19 C20 C25 58.7(4) . . . . ?
C25 C20 C21 C22 3.0(6) . . . . ?
C19 C20 C21 C22 -173.7(4) . . . . ?
C20 C21 C22 C23 0.1(7) . . . . ?
C21 C22 C23 C24 -2.7(7) . . . . ?
C21 C22 C23 Cl1 175.6(7) . . . . ?
C21 C22 C23 Br1 174.4(4) . . . . ?
C22 C23 C24 C25 2.1(7) . . . . ?
Cl1 C23 C24 C25 -176.6(6) . . . . ?
Br1 C23 C24 C25 -174.7(4) . . . . ?
C21 C20 C25 C24 -3.6(6) . . . . ?
C19 C20 C25 C24 173.1(4) . . . . ?
C23 C24 C25 C20 1.1(7) . . . . ?
C19 Se1 C26 C27 28.5(4) . . . . ?
C19 Se1 C26 C31 -155.6(3) . . . . ?
C31 C26 C27 C28 -0.4(7) . . . . ?
Se1 C26 C27 C28 175.5(3) . . . . ?
C26 C27 C28 C29 0.1(7) . . . . ?
C27 C28 C29 C30 0.0(8) . . . . ?
C28 C29 C30 C31 0.2(9) . . . . ?
C29 C30 C31 C26 -0.4(8) . . . . ?
C27 C26 C31 C30 0.5(7) . . . . ?
Se1 C26 C31 C30 -175.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.078
