# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Joan Bosch'
_publ_contact_author_email       JOANBOSCH@UB.EDU

_publ_section_title              
;
Enantioselective total synthesis of the indole alkaloid
16-episilicine
;
_publ_requested_category         FO
loop_
_publ_author_name
'Joan Bosch'
'Mercedes Amat'
'Begona Checa'
'Nuria Llor'
'Elies Molins'

# Attachment 'archive_jb68d.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-11-07 at 20:14:05
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : jb68d difabs dreduc struct

data_jb68d
_database_code_depnum_ccdc_archive 'CCDC 708534'

_audit_creation_date             2008-11-07T20:14:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C32 H30 N2 O4 S1'
_chemical_formula_sum            'C32 H30 N2 O4 S1'
_chemical_formula_weight         538.64
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.004(5)
_cell_length_b                   14.264(3)
_cell_length_c                   20.840(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2676.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    565(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      9.2
_cell_measurement_theta_max      15.3
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.9054
_exptl_absorpt_correction_T_max  0.9696

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      565(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.019789
_diffrn_orient_matrix_ub_12      -0.000662
_diffrn_orient_matrix_ub_13      -0.047221
_diffrn_orient_matrix_ub_21      0.002195
_diffrn_orient_matrix_ub_22      -0.070118
_diffrn_orient_matrix_ub_23      0.000633
_diffrn_orient_matrix_ub_31      -0.109321
_diffrn_orient_matrix_ub_32      -0.001742
_diffrn_orient_matrix_ub_33      -0.008594
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 2 2
2 2 -2

_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_number            2660
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         24.94
_diffrn_reflns_theta_full        24.94
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2660
_reflns_number_gt                1701
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0364P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.097
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(15)
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
S1 S 0.28633(14) 0.09470(9) 0.88826(7) 0.0521(4) Uani 1 1 d . . .
O1 O 0.5025(4) 0.6802(2) 0.85517(17) 0.0605(10) Uani 1 1 d . . .
O2 O 0.3005(4) -0.0044(2) 0.88575(18) 0.0698(10) Uani 1 1 d . . .
O3 O 0.1497(3) 0.1381(2) 0.87080(17) 0.0653(11) Uani 1 1 d . . .
O5 O 0.8295(4) 0.4911(2) 0.78792(18) 0.0688(11) Uani 1 1 d . . .
N4 N 0.6938(4) 0.5781(2) 0.85668(17) 0.0432(10) Uani 1 1 d . . .
N69 N 0.4163(4) 0.1384(2) 0.83964(18) 0.0425(10) Uani 1 1 d . . .
C2 C 0.6317(5) 0.7367(3) 0.8470(3) 0.0572(15) Uani 1 1 d . . .
H2A H 0.6507 0.7736 0.8852 0.069 Uiso 1 1 calc R . .
H2B H 0.6197 0.7788 0.8108 0.069 Uiso 1 1 calc R . .
C3 C 0.7612(5) 0.6664(3) 0.8346(2) 0.0486(13) Uani 1 1 d . . .
H3 H 0.7807 0.6625 0.7884 0.058 Uiso 1 1 calc R . .
C5 C 0.7210(6) 0.4972(3) 0.8230(2) 0.0440(12) Uani 1 1 d . . .
C6 C 0.6110(4) 0.4179(3) 0.8310(2) 0.0387(11) Uani 1 1 d . . .
H6 H 0.6292 0.389 0.873 0.046 Uiso 1 1 calc R . .
C7 C 0.4539(4) 0.4609(3) 0.8324(2) 0.0412(12) Uani 1 1 d . . .
H7 H 0.4474 0.5029 0.7952 0.049 Uiso 1 1 calc R . .
C8 C 0.4418(5) 0.5235(3) 0.8925(2) 0.0445(11) Uani 1 1 d . . .
H8 H 0.3436 0.5531 0.8917 0.053 Uiso 1 1 calc R . .
C8A C 0.5562(5) 0.6007(3) 0.8899(2) 0.0471(12) Uani 1 1 d . . .
H8A H 0.5799 0.6202 0.9339 0.056 Uiso 1 1 calc R . .
C31 C 0.8997(5) 0.6952(4) 0.8686(3) 0.0557(15) Uani 1 1 d . . .
C32 C 0.9363(7) 0.6607(4) 0.9284(3) 0.084(2) Uani 1 1 d . . .
H32 H 0.876 0.6156 0.9473 0.101 Uiso 1 1 calc R . .
C33 C 1.0616(8) 0.6922(6) 0.9609(4) 0.115(3) Uani 1 1 d . . .
H33 H 1.0846 0.6696 1.0016 0.139 Uiso 1 1 calc R . .
C34 C 1.1502(9) 0.7574(7) 0.9315(6) 0.138(5) Uani 1 1 d . . .
H34 H 1.2361 0.7775 0.9522 0.165 Uiso 1 1 calc R . .
C35 C 1.1164(9) 0.7930(6) 0.8739(5) 0.124(4) Uani 1 1 d . . .
H35 H 1.1769 0.8385 0.8555 0.149 Uiso 1 1 calc R . .
C36 C 0.9907(6) 0.7617(4) 0.8415(3) 0.082(2) Uani 1 1 d . . .
H36 H 0.968 0.7859 0.8012 0.098 Uiso 1 1 calc R . .
C61 C 0.6324(5) 0.3429(3) 0.7804(2) 0.0450(12) Uani 1 1 d . . .
H61A H 0.5826 0.3618 0.7412 0.054 Uiso 1 1 calc R . .
H61B H 0.7375 0.3365 0.7711 0.054 Uiso 1 1 calc R . .
C62 C 0.5720(5) 0.2503(3) 0.8021(2) 0.0414(12) Uani 1 1 d . . .
C63 C 0.6514(5) 0.1626(3) 0.8047(2) 0.0402(12) Uani 1 1 d . . .
C64 C 0.7977(6) 0.1371(3) 0.7878(2) 0.0525(13) Uani 1 1 d . . .
H64 H 0.8619 0.1809 0.7698 0.063 Uiso 1 1 calc R . .
C65 C 0.8433(6) 0.0477(4) 0.7983(2) 0.0592(15) Uani 1 1 d . . .
H65 H 0.9393 0.0302 0.787 0.071 Uiso 1 1 calc R . .
C66 C 0.7491(6) -0.0180(3) 0.8257(2) 0.0568(14) Uani 1 1 d . . .
H66 H 0.7839 -0.0783 0.8334 0.068 Uiso 1 1 calc R . .
C67 C 0.6047(6) 0.0047(3) 0.8416(2) 0.0510(14) Uani 1 1 d . . .
H67 H 0.5415 -0.0397 0.8596 0.061 Uiso 1 1 calc R . .
C68 C 0.5569(5) 0.0948(3) 0.8302(2) 0.0435(12) Uani 1 1 d . . .
C71 C 0.3237(5) 0.3965(3) 0.8282(2) 0.0468(12) Uani 1 1 d . . .
H71 H 0.2327 0.4272 0.8265 0.056 Uiso 1 1 calc R . .
C72 C 0.3131(5) 0.3027(3) 0.8266(2) 0.0472(12) Uani 1 1 d . . .
H72 H 0.2174 0.2782 0.8274 0.057 Uiso 1 1 calc R . .
C73 C 0.4324(5) 0.2353(3) 0.8238(2) 0.0429(12) Uani 1 1 d . . .
C74 C 0.3383(5) 0.1329(3) 0.9643(2) 0.0514(13) Uani 1 1 d . . .
C75 C 0.4326(6) 0.0788(4) 1.0010(3) 0.0722(17) Uani 1 1 d . . .
H75 H 0.4714 0.0232 0.9847 0.087 Uiso 1 1 calc R . .
C76 C 0.4687(7) 0.1081(6) 1.0617(3) 0.087(2) Uani 1 1 d . . .
H76 H 0.5304 0.0713 1.0872 0.105 Uiso 1 1 calc R . .
C77 C 0.4149(7) 0.1904(6) 1.0851(3) 0.082(2) Uani 1 1 d . . .
H77 H 0.4418 0.2102 1.126 0.099 Uiso 1 1 calc R . .
C78 C 0.3217(8) 0.2441(4) 1.0489(3) 0.0792(19) Uani 1 1 d . . .
H78 H 0.2854 0.3002 1.0653 0.095 Uiso 1 1 calc R . .
C79 C 0.2808(6) 0.2154(4) 0.9878(3) 0.0652(15) Uani 1 1 d . . .
H79 H 0.2159 0.2512 0.9632 0.078 Uiso 1 1 calc R . .
C81 C 0.4543(6) 0.4685(3) 0.9558(2) 0.0628(15) Uani 1 1 d . . .
H81A H 0.405 0.4086 0.9507 0.075 Uiso 1 1 calc R . .
H81B H 0.5584 0.4562 0.9644 0.075 Uiso 1 1 calc R . .
C82 C 0.3881(7) 0.5184(4) 1.0130(3) 0.091(2) Uani 1 1 d . . .
H82A H 0.4352 0.5783 1.0182 0.136 Uiso 1 1 calc R . .
H82B H 0.4035 0.4814 1.0509 0.136 Uiso 1 1 calc R . .
H82C H 0.2835 0.5271 1.0063 0.136 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0427(7) 0.0482(7) 0.0652(9) 0.0019(7) -0.0006(7) -0.0175(7)
O1 0.051(2) 0.040(2) 0.091(3) 0.010(2) -0.007(2) -0.0010(19)
O2 0.069(2) 0.0403(18) 0.100(3) 0.000(2) 0.001(2) -0.0259(19)
O3 0.0353(19) 0.074(2) 0.086(3) 0.014(2) -0.0056(19) -0.0105(19)
O5 0.056(2) 0.056(2) 0.094(3) -0.010(2) 0.029(2) -0.015(2)
N4 0.039(2) 0.035(2) 0.056(2) -0.0026(19) 0.004(2) -0.0031(19)
N69 0.036(2) 0.043(2) 0.049(2) 0.002(2) -0.001(2) -0.0081(19)
C2 0.054(3) 0.043(3) 0.075(4) 0.011(3) -0.006(3) -0.005(3)
C3 0.052(3) 0.034(3) 0.059(3) 0.006(2) -0.001(3) -0.007(2)
C5 0.040(3) 0.046(3) 0.047(3) 0.003(2) -0.001(3) -0.006(3)
C6 0.036(3) 0.039(3) 0.041(3) 0.006(2) 0.002(2) -0.002(2)
C7 0.035(3) 0.039(3) 0.050(3) 0.006(2) 0.001(2) 0.001(2)
C8 0.033(2) 0.047(3) 0.053(3) -0.001(3) 0.004(3) 0.003(2)
C8A 0.046(3) 0.043(3) 0.052(3) 0.000(3) -0.002(3) 0.000(3)
C31 0.045(3) 0.041(3) 0.081(4) -0.009(3) 0.004(3) -0.003(3)
C32 0.063(4) 0.069(4) 0.121(6) -0.009(4) -0.032(4) -0.012(4)
C33 0.069(5) 0.128(7) 0.149(8) -0.035(6) -0.048(5) -0.003(5)
C34 0.044(5) 0.162(10) 0.206(12) -0.112(10) -0.015(7) -0.004(6)
C35 0.064(6) 0.119(7) 0.190(10) -0.087(8) 0.050(6) -0.041(5)
C36 0.063(4) 0.075(4) 0.108(5) -0.030(4) 0.031(4) -0.015(4)
C61 0.041(3) 0.041(3) 0.053(3) 0.000(2) 0.002(3) -0.009(2)
C62 0.038(3) 0.043(3) 0.043(3) -0.002(2) 0.002(2) -0.006(2)
C63 0.039(3) 0.041(3) 0.041(3) -0.012(2) 0.001(2) -0.003(2)
C64 0.054(3) 0.049(3) 0.055(3) -0.012(3) 0.010(3) -0.006(3)
C65 0.046(3) 0.053(3) 0.078(4) -0.016(3) 0.005(3) 0.006(3)
C66 0.065(4) 0.044(3) 0.062(4) -0.007(3) -0.011(3) 0.001(3)
C67 0.061(4) 0.039(3) 0.053(3) -0.004(3) -0.004(3) -0.006(3)
C68 0.045(3) 0.039(3) 0.047(3) -0.001(3) -0.005(3) -0.003(3)
C71 0.036(3) 0.052(3) 0.052(3) 0.000(3) -0.002(2) -0.001(3)
C72 0.029(3) 0.053(3) 0.060(3) 0.005(3) 0.006(3) -0.004(2)
C73 0.044(3) 0.036(3) 0.048(3) -0.001(2) 0.000(3) -0.003(2)
C74 0.042(3) 0.052(3) 0.060(3) 0.005(3) 0.003(3) -0.018(3)
C75 0.057(4) 0.083(4) 0.076(4) 0.011(4) 0.002(3) 0.005(4)
C76 0.060(4) 0.137(7) 0.064(5) 0.008(5) -0.007(3) -0.002(5)
C77 0.070(5) 0.117(6) 0.061(4) -0.015(4) 0.013(4) -0.042(4)
C78 0.097(5) 0.076(4) 0.065(4) -0.003(4) 0.013(4) -0.011(4)
C79 0.067(4) 0.068(4) 0.060(4) 0.008(3) 0.006(3) -0.002(3)
C81 0.067(4) 0.055(3) 0.066(4) 0.001(3) 0.012(3) -0.013(3)
C82 0.093(5) 0.111(5) 0.069(4) -0.009(4) 0.021(4) -0.004(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 1.420(3) . ?
S1 O3 1.425(3) . ?
S1 N69 1.669(4) . ?
S1 C74 1.741(5) . ?
O1 C2 1.425(5) . ?
O1 C8A 1.430(5) . ?
O5 C5 1.223(5) . ?
N4 C5 1.372(6) . ?
N4 C8A 1.456(5) . ?
N4 C3 1.472(5) . ?
N69 C68 1.424(5) . ?
N69 C73 1.428(5) . ?
C2 C3 1.559(6) . ?
C3 C31 1.492(6) . ?
C5 C6 1.513(6) . ?
C6 C61 1.514(6) . ?
C6 C7 1.543(6) . ?
C7 C71 1.492(6) . ?
C7 C8 1.543(6) . ?
C8 C8A 1.509(6) . ?
C8 C81 1.538(6) . ?
C31 C36 1.375(7) . ?
C31 C32 1.380(7) . ?
C32 C33 1.391(8) . ?
C33 C34 1.370(11) . ?
C34 C35 1.339(12) . ?
C35 C36 1.392(9) . ?
C61 C62 1.499(5) . ?
C62 C73 1.353(6) . ?
C62 C63 1.441(6) . ?
C63 C68 1.393(6) . ?
C63 C64 1.412(6) . ?
C64 C65 1.359(6) . ?
C65 C66 1.386(6) . ?
C66 C67 1.380(6) . ?
C67 C68 1.376(6) . ?
C71 C72 1.342(6) . ?
C72 C73 1.442(6) . ?
C74 C79 1.376(6) . ?
C74 C75 1.378(7) . ?
C75 C76 1.372(8) . ?
C76 C77 1.360(8) . ?
C77 C78 1.363(8) . ?
C78 C79 1.387(7) . ?
C81 C82 1.511(6) . ?

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 O3 120.1(2) . . ?
O2 S1 N69 106.6(2) . . ?
O3 S1 N69 106.8(2) . . ?
O2 S1 C74 108.7(2) . . ?
O3 S1 C74 109.2(3) . . ?
N69 S1 C74 104.3(2) . . ?
C2 O1 C8A 103.5(3) . . ?
C5 N4 C8A 125.5(4) . . ?
C5 N4 C3 119.1(4) . . ?
C8A N4 C3 108.1(3) . . ?
C68 N69 C73 107.5(4) . . ?
C68 N69 S1 123.0(3) . . ?
C73 N69 S1 124.9(3) . . ?
O1 C2 C3 105.5(4) . . ?
N4 C3 C31 115.6(4) . . ?
N4 C3 C2 100.9(3) . . ?
C31 C3 C2 111.7(4) . . ?
O5 C5 N4 120.5(4) . . ?
O5 C5 C6 122.3(4) . . ?
N4 C5 C6 117.1(4) . . ?
C5 C6 C61 111.6(4) . . ?
C5 C6 C7 107.7(4) . . ?
C61 C6 C7 114.2(4) . . ?
C71 C7 C8 110.3(4) . . ?
C71 C7 C6 118.3(3) . . ?
C8 C7 C6 108.0(4) . . ?
C8A C8 C81 110.6(4) . . ?
C8A C8 C7 110.2(4) . . ?
C81 C8 C7 113.4(4) . . ?
O1 C8A N4 102.8(4) . . ?
O1 C8A C8 111.5(4) . . ?
N4 C8A C8 115.9(4) . . ?
C36 C31 C32 118.4(6) . . ?
C36 C31 C3 119.5(6) . . ?
C32 C31 C3 122.1(5) . . ?
C31 C32 C33 121.3(7) . . ?
C34 C33 C32 118.3(9) . . ?
C35 C34 C33 121.8(9) . . ?
C34 C35 C36 119.9(9) . . ?
C31 C36 C35 120.4(7) . . ?
C62 C61 C6 111.5(4) . . ?
C73 C62 C63 108.1(4) . . ?
C73 C62 C61 125.2(4) . . ?
C63 C62 C61 126.6(4) . . ?
C68 C63 C64 119.1(4) . . ?
C68 C63 C62 108.3(4) . . ?
C64 C63 C62 132.6(4) . . ?
C65 C64 C63 118.9(5) . . ?
C64 C65 C66 121.1(5) . . ?
C67 C66 C65 121.1(5) . . ?
C68 C67 C66 118.1(5) . . ?
C67 C68 C63 121.6(4) . . ?
C67 C68 N69 131.5(4) . . ?
C63 C68 N69 107.0(4) . . ?
C72 C71 C7 132.2(4) . . ?
C71 C72 C73 127.7(4) . . ?
C62 C73 N69 108.9(4) . . ?
C62 C73 C72 126.9(4) . . ?
N69 C73 C72 124.1(4) . . ?
C79 C74 C75 120.9(5) . . ?
C79 C74 S1 119.4(5) . . ?
C75 C74 S1 119.7(5) . . ?
C76 C75 C74 119.1(6) . . ?
C77 C76 C75 120.6(7) . . ?
C76 C77 C78 120.4(6) . . ?
C77 C78 C79 120.3(6) . . ?
C74 C79 C78 118.6(6) . . ?
C82 C81 C8 114.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N69 C68 -32.8(4) . . . . ?
O3 S1 N69 C68 -162.3(3) . . . . ?
C74 S1 N69 C68 82.2(4) . . . . ?
O2 S1 N69 C73 174.3(4) . . . . ?
O3 S1 N69 C73 44.8(4) . . . . ?
C74 S1 N69 C73 -70.8(4) . . . . ?
C8A O1 C2 C3 37.7(5) . . . . ?
C5 N4 C3 C31 -98.4(5) . . . . ?
C8A N4 C3 C31 109.8(4) . . . . ?
C5 N4 C3 C2 140.9(4) . . . . ?
C8A N4 C3 C2 -10.9(5) . . . . ?
O1 C2 C3 N4 -16.2(5) . . . . ?
O1 C2 C3 C31 -139.6(4) . . . . ?
C8A N4 C5 O5 167.6(4) . . . . ?
C3 N4 C5 O5 21.2(7) . . . . ?
C8A N4 C5 C6 -11.8(6) . . . . ?
C3 N4 C5 C6 -158.3(4) . . . . ?
O5 C5 C6 C61 -13.0(6) . . . . ?
N4 C5 C6 C61 166.5(4) . . . . ?
O5 C5 C6 C7 -139.1(5) . . . . ?
N4 C5 C6 C7 40.3(5) . . . . ?
C5 C6 C7 C71 169.4(4) . . . . ?
C61 C6 C7 C71 44.8(6) . . . . ?
C5 C6 C7 C8 -64.4(4) . . . . ?
C61 C6 C7 C8 171.0(4) . . . . ?
C71 C7 C8 C8A -169.0(4) . . . . ?
C6 C7 C8 C8A 60.2(4) . . . . ?
C71 C7 C8 C81 66.4(5) . . . . ?
C6 C7 C8 C81 -64.4(5) . . . . ?
C2 O1 C8A N4 -44.3(4) . . . . ?
C2 O1 C8A C8 -169.1(4) . . . . ?
C5 N4 C8A O1 -115.3(5) . . . . ?
C3 N4 C8A O1 34.2(4) . . . . ?
C5 N4 C8A C8 6.6(7) . . . . ?
C3 N4 C8A C8 156.1(4) . . . . ?
C81 C8 C8A O1 -147.5(4) . . . . ?
C7 C8 C8A O1 86.4(4) . . . . ?
C81 C8 C8A N4 95.4(5) . . . . ?
C7 C8 C8A N4 -30.8(5) . . . . ?
N4 C3 C31 C36 163.3(5) . . . . ?
C2 C3 C31 C36 -82.1(6) . . . . ?
N4 C3 C31 C32 -20.1(7) . . . . ?
C2 C3 C31 C32 94.5(6) . . . . ?
C36 C31 C32 C33 0.2(9) . . . . ?
C3 C31 C32 C33 -176.4(5) . . . . ?
C31 C32 C33 C34 -1.2(11) . . . . ?
C32 C33 C34 C35 2.1(14) . . . . ?
C33 C34 C35 C36 -1.9(15) . . . . ?
C32 C31 C36 C35 0.0(9) . . . . ?
C3 C31 C36 C35 176.8(5) . . . . ?
C34 C35 C36 C31 0.8(12) . . . . ?
C5 C6 C61 C62 156.9(4) . . . . ?
C7 C6 C61 C62 -80.7(5) . . . . ?
C6 C61 C62 C73 53.5(6) . . . . ?
C6 C61 C62 C63 -125.2(5) . . . . ?
C73 C62 C63 C68 -1.5(5) . . . . ?
C61 C62 C63 C68 177.5(4) . . . . ?
C73 C62 C63 C64 179.4(5) . . . . ?
C61 C62 C63 C64 -1.6(8) . . . . ?
C68 C63 C64 C65 -1.6(7) . . . . ?
C62 C63 C64 C65 177.4(5) . . . . ?
C63 C64 C65 C66 -0.6(8) . . . . ?
C64 C65 C66 C67 1.7(8) . . . . ?
C65 C66 C67 C68 -0.6(7) . . . . ?
C66 C67 C68 C63 -1.6(7) . . . . ?
C66 C67 C68 N69 178.3(4) . . . . ?
C64 C63 C68 C67 2.7(7) . . . . ?
C62 C63 C68 C67 -176.5(4) . . . . ?
C64 C63 C68 N69 -177.2(4) . . . . ?
C62 C63 C68 N69 3.6(5) . . . . ?
C73 N69 C68 C67 175.8(5) . . . . ?
S1 N69 C68 C67 18.9(7) . . . . ?
C73 N69 C68 C63 -4.3(5) . . . . ?
S1 N69 C68 C63 -161.3(3) . . . . ?
C8 C7 C71 C72 -121.1(6) . . . . ?
C6 C7 C71 C72 4.0(8) . . . . ?
C7 C71 C72 C73 -4.9(9) . . . . ?
C63 C62 C73 N69 -1.3(5) . . . . ?
C61 C62 C73 N69 179.8(4) . . . . ?
C63 C62 C73 C72 -176.8(4) . . . . ?
C61 C62 C73 C72 4.2(8) . . . . ?
C68 N69 C73 C62 3.5(5) . . . . ?
S1 N69 C73 C62 159.9(3) . . . . ?
C68 N69 C73 C72 179.2(4) . . . . ?
S1 N69 C73 C72 -24.4(6) . . . . ?
C71 C72 C73 C62 -22.9(8) . . . . ?
C71 C72 C73 N69 162.1(5) . . . . ?
O2 S1 C74 C79 -153.9(4) . . . . ?
O3 S1 C74 C79 -21.2(4) . . . . ?
N69 S1 C74 C79 92.6(4) . . . . ?
O2 S1 C74 C75 24.1(5) . . . . ?
O3 S1 C74 C75 156.8(4) . . . . ?
N69 S1 C74 C75 -89.3(4) . . . . ?
C79 C74 C75 C76 0.3(8) . . . . ?
S1 C74 C75 C76 -177.7(4) . . . . ?
C74 C75 C76 C77 -1.5(9) . . . . ?
C75 C76 C77 C78 1.4(9) . . . . ?
C76 C77 C78 C79 -0.1(9) . . . . ?
C75 C74 C79 C78 1.1(8) . . . . ?
S1 C74 C79 C78 179.1(4) . . . . ?
C77 C78 C79 C74 -1.2(9) . . . . ?
C8A C8 C81 C82 77.2(6) . . . . ?
C7 C8 C81 C82 -158.5(4) . . . . ?