# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Prof Shengming Ma'
_publ_contact_author_address     
;
State Key Laboratory of Organometallic Chemistry
Shanghai Institute of Organic Chemistry
Chinese Academy of Sciences
Shanghai
200032
CHINA
;

_publ_contact_author_email       MASM@MAIL.SIOC.AC.CN

_publ_section_title              
;
NaI-Catalyzed Highly Regioselective Ring-Opening
[1+2] Cycloaddition Reaction of Cyclopropenes with Imines. Highly
Stereoselective Synthesis of cis-Vinylic Aziridines
;
loop_
_publ_author_name
'Shengming Ma'
'Yangjun Cai'
'Harong Hou'
'Xin Jin'
'Lianghua Lu'
;
Junliang Zhang
;

data_4aa
_database_code_depnum_ccdc_archive 'CCDC 227385'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 N O6 S'
_chemical_formula_weight         471.55

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.211(2)
_cell_length_b                   8.6072(16)
_cell_length_c                   26.662(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.710(4)
_cell_angle_gamma                90.00
_cell_volume                     2535.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    965
_cell_measurement_theta_min      4.980
_cell_measurement_theta_max      35.465

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   sadabs
_exptl_absorpt_correction_T_min  0.55043
_exptl_absorpt_correction_T_max  1.00000
_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            14986
_diffrn_reflns_av_R_equivalents  0.1523
_diffrn_reflns_av_sigmaI/netI    0.2239
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.29
_reflns_number_total             5885
_reflns_number_gt                1636
_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 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^)+(0.0701P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0003(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5885
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2185
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   0.729
_refine_ls_restrained_S_all      0.729
_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
S S 0.53426(11) -0.13160(15) 0.84505(4) 0.0737(4) Uani 1 1 d . . .
N1 N 0.6450(3) -0.0280(4) 0.87978(11) 0.0585(9) Uani 1 1 d . . .
O1 O 0.8722(3) 0.5733(5) 0.8742(2) 0.1516(19) Uani 1 1 d . . .
O2 O 0.9588(3) 0.4318(4) 0.93640(14) 0.1104(12) Uani 1 1 d . . .
O3 O 0.5692(3) 0.3915(3) 0.93161(11) 0.0761(9) Uani 1 1 d . . .
O4 O 0.7214(3) 0.5443(4) 0.96616(12) 0.1003(11) Uani 1 1 d . . .
O5 O 0.4236(3) -0.0438(4) 0.83540(11) 0.0930(10) Uani 1 1 d . . .
O6 O 0.5357(3) -0.2779(3) 0.86983(11) 0.0991(11) Uani 1 1 d . . .
C1 C 0.6090(4) 0.0498(5) 0.92443(15) 0.0588(11) Uani 1 1 d . . .
C2 C 0.6328(4) 0.1413(5) 0.87951(16) 0.0570(11) Uani 1 1 d . . .
C3 C 0.7451(3) 0.2344(5) 0.87982(14) 0.0572(11) Uani 1 1 d . . .
C4 C 0.8346(5) 0.1737(7) 0.8481(2) 0.0753(15) Uani 1 1 d . . .
C5 C 0.8016(4) 0.2245(6) 0.79207(18) 0.0998(16) Uani 1 1 d . . .
H6 H 0.7239 0.1798 0.7777 0.120 Uiso 1 1 calc R . .
H5 H 0.7932 0.3366 0.7907 0.120 Uiso 1 1 calc R . .
C6 C 0.8924(5) 0.1772(8) 0.7606(2) 0.142(2) Uani 1 1 d . . .
H7 H 0.9712 0.2155 0.7764 0.170 Uiso 1 1 calc R . .
H8 H 0.8966 0.0647 0.7600 0.170 Uiso 1 1 calc R . .
C7 C 0.8668(6) 0.2336(9) 0.7085(3) 0.185(3) Uani 1 1 d . . .
H11 H 0.7871 0.2015 0.6931 0.277 Uiso 1 1 calc R . .
H10 H 0.9251 0.1916 0.6896 0.277 Uiso 1 1 calc R . .
H9 H 0.8715 0.3450 0.7084 0.277 Uiso 1 1 calc R . .
C8 C 0.7615(4) 0.3679(5) 0.90466(15) 0.0635(11) Uani 1 1 d . . .
C9 C 0.8716(5) 0.4741(8) 0.9034(2) 0.0902(16) Uani 1 1 d . . .
C10 C 1.0551(5) 0.5577(9) 0.9359(3) 0.210(4) Uani 1 1 d . . .
H12 H 1.1179 0.5190 0.9188 0.315 Uiso 1 1 calc R . .
H14 H 1.0890 0.5854 0.9702 0.315 Uiso 1 1 calc R . .
H13 H 1.0187 0.6477 0.9182 0.315 Uiso 1 1 calc R . .
C11 C 0.6710(4) 0.4337(5) 0.93477(16) 0.0671(12) Uani 1 1 d . . .
C12 C 0.6432(5) 0.6129(5) 0.9975(2) 0.121(2) Uani 1 1 d . . .
H15 H 0.5696 0.6463 0.9766 0.182 Uiso 1 1 calc R . .
H16 H 0.6829 0.7006 1.0153 0.182 Uiso 1 1 calc R . .
H17 H 0.6250 0.5376 1.0217 0.182 Uiso 1 1 calc R . .
C13 C 0.6936(4) 0.0387(5) 0.97337(15) 0.0625(11) Uani 1 1 d . . .
C14 C 0.6620(4) 0.1083(5) 1.01582(18) 0.0810(14) Uani 1 1 d . . .
H18 H 0.5894 0.1626 1.0128 0.097 Uiso 1 1 calc R . .
C15 C 0.7360(6) 0.0992(7) 1.0627(2) 0.114(2) Uani 1 1 d . . .
H19 H 0.7144 0.1485 1.0909 0.136 Uiso 1 1 calc R . .
C16 C 0.8413(6) 0.0169(8) 1.0672(2) 0.123(2) Uani 1 1 d . . .
H20 H 0.8913 0.0094 1.0986 0.148 Uiso 1 1 calc R . .
C17 C 0.8737(4) -0.0544(7) 1.0259(3) 0.111(2) Uani 1 1 d . . .
H21 H 0.9452 -0.1113 1.0295 0.133 Uiso 1 1 calc R . .
C18 C 0.8007(4) -0.0425(6) 0.97854(18) 0.0851(14) Uani 1 1 d . . .
H22 H 0.8242 -0.0893 0.9503 0.102 Uiso 1 1 calc R . .
C19 C 0.5901(4) -0.1496(5) 0.78815(16) 0.0615(11) Uani 1 1 d . . .
C20 C 0.5378(4) -0.0719(5) 0.74615(18) 0.0756(13) Uani 1 1 d . . .
H23 H 0.4715 -0.0080 0.7474 0.091 Uiso 1 1 calc R . .
C21 C 0.5824(5) -0.0873(5) 0.70172(18) 0.0852(14) Uani 1 1 d . . .
H24 H 0.5451 -0.0333 0.6731 0.102 Uiso 1 1 calc R . .
C22 C 0.6795(5) -0.1789(6) 0.69783(19) 0.0821(14) Uani 1 1 d . . .
C23 C 0.7312(4) -0.2581(6) 0.7410(2) 0.0881(15) Uani 1 1 d . . .
H25 H 0.7970 -0.3227 0.7395 0.106 Uiso 1 1 calc R . .
C24 C 0.6883(4) -0.2441(5) 0.78622(18) 0.0795(13) Uani 1 1 d . . .
H26 H 0.7250 -0.2977 0.8150 0.095 Uiso 1 1 calc R . .
C25 C 0.7276(5) -0.1978(7) 0.64913(19) 0.131(2) Uani 1 1 d . . .
H27 H 0.8105 -0.1646 0.6540 0.196 Uiso 1 1 calc R . .
H28 H 0.6806 -0.1358 0.6231 0.196 Uiso 1 1 calc R . .
H29 H 0.7226 -0.3050 0.6391 0.196 Uiso 1 1 calc R . .
H1 H 0.529(3) 0.042(4) 0.9241(13) 0.062(12) Uiso 1 1 d . . .
H2 H 0.569(3) 0.183(4) 0.8575(12) 0.050(12) Uiso 1 1 d . . .
H3 H 0.912(4) 0.208(4) 0.8614(16) 0.090(16) Uiso 1 1 d . . .
H4 H 0.839(3) 0.066(4) 0.8495(14) 0.068(14) Uiso 1 1 d . . .

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
S 0.0824(9) 0.0754(9) 0.0649(8) -0.0114(7) 0.0170(6) -0.0201(7)
N1 0.071(2) 0.055(2) 0.052(2) -0.0105(17) 0.0143(16) -0.0100(17)
O1 0.082(3) 0.151(4) 0.219(5) 0.091(3) 0.017(3) -0.032(2)
O2 0.089(3) 0.155(3) 0.083(3) 0.031(2) 0.003(2) -0.042(2)
O3 0.074(2) 0.073(2) 0.089(2) -0.0085(16) 0.0384(17) -0.0159(17)
O4 0.102(3) 0.112(3) 0.099(3) -0.049(2) 0.054(2) -0.048(2)
O5 0.062(2) 0.123(3) 0.097(3) -0.0263(19) 0.0188(16) -0.0087(19)
O6 0.148(3) 0.073(2) 0.078(2) 0.0041(17) 0.023(2) -0.041(2)
C1 0.058(3) 0.062(3) 0.058(3) -0.003(2) 0.017(2) -0.011(2)
C2 0.061(3) 0.063(3) 0.050(3) 0.002(2) 0.019(2) -0.006(3)
C3 0.060(3) 0.068(3) 0.048(3) 0.005(2) 0.020(2) -0.008(2)
C4 0.067(4) 0.079(4) 0.088(4) -0.007(3) 0.035(3) -0.005(3)
C5 0.096(4) 0.145(5) 0.065(4) -0.010(3) 0.033(3) -0.010(3)
C6 0.130(5) 0.235(7) 0.076(4) -0.019(4) 0.059(4) -0.015(5)
C7 0.198(7) 0.269(9) 0.107(6) 0.001(6) 0.080(5) -0.011(6)
C8 0.066(3) 0.073(3) 0.057(3) -0.006(2) 0.027(2) -0.016(3)
C9 0.082(4) 0.140(5) 0.055(3) -0.003(3) 0.031(3) -0.012(4)
C10 0.109(5) 0.362(11) 0.172(7) -0.088(7) 0.060(4) -0.142(6)
C11 0.087(4) 0.064(3) 0.057(3) -0.004(2) 0.031(3) -0.017(3)
C12 0.146(5) 0.115(4) 0.124(5) -0.061(4) 0.086(4) -0.043(4)
C13 0.070(3) 0.074(3) 0.048(3) 0.004(2) 0.021(2) -0.025(2)
C14 0.078(3) 0.113(4) 0.055(3) -0.004(3) 0.016(3) -0.016(3)
C15 0.109(5) 0.173(6) 0.064(4) -0.011(4) 0.030(4) -0.046(4)
C16 0.094(5) 0.206(7) 0.069(4) 0.025(4) 0.012(4) -0.062(5)
C17 0.069(4) 0.160(5) 0.102(5) 0.058(4) 0.009(4) -0.010(3)
C18 0.065(3) 0.118(4) 0.071(4) 0.017(3) 0.009(3) -0.002(3)
C19 0.071(3) 0.055(3) 0.059(3) -0.007(2) 0.010(2) -0.004(2)
C20 0.089(3) 0.070(3) 0.065(3) 0.000(3) 0.009(3) 0.011(3)
C21 0.107(4) 0.086(4) 0.057(3) 0.004(3) 0.000(3) 0.002(3)
C22 0.088(4) 0.092(4) 0.068(4) -0.015(3) 0.018(3) -0.018(3)
C23 0.080(4) 0.103(4) 0.080(4) -0.014(3) 0.010(3) 0.012(3)
C24 0.085(4) 0.075(3) 0.075(4) 0.004(3) 0.003(3) 0.003(3)
C25 0.142(5) 0.169(6) 0.096(5) -0.029(4) 0.064(4) -0.028(4)

_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
S O6 1.421(3) . ?
S O5 1.439(3) . ?
S N1 1.675(3) . ?
S C19 1.743(4) . ?
N1 C2 1.464(5) . ?
N1 C1 1.481(5) . ?
O1 C9 1.156(6) . ?
O2 C9 1.253(6) . ?
O2 C10 1.531(6) . ?
O3 C11 1.187(4) . ?
O4 C11 1.329(5) . ?
O4 C12 1.437(4) . ?
C1 C13 1.481(5) . ?
C1 C2 1.495(5) . ?
C1 H1 0.90(3) . ?
C2 C3 1.491(5) . ?
C2 H2 0.92(3) . ?
C3 C8 1.323(5) . ?
C3 C4 1.511(5) . ?
C4 C5 1.540(6) . ?
C4 H3 0.93(4) . ?
C4 H4 0.93(3) . ?
C5 C6 1.482(6) . ?
C5 H6 0.9700 . ?
C5 H5 0.9700 . ?
C6 C7 1.453(8) . ?
C6 H7 0.9700 . ?
C6 H8 0.9700 . ?
C7 H11 0.9600 . ?
C7 H10 0.9600 . ?
C7 H9 0.9600 . ?
C8 C11 1.506(5) . ?
C8 C9 1.542(6) . ?
C10 H12 0.9600 . ?
C10 H14 0.9600 . ?
C10 H13 0.9600 . ?
C12 H15 0.9600 . ?
C12 H16 0.9600 . ?
C12 H17 0.9600 . ?
C13 C18 1.376(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.381(6) . ?
C14 H18 0.9300 . ?
C15 C16 1.364(7) . ?
C15 H19 0.9300 . ?
C16 C17 1.361(8) . ?
C16 H20 0.9300 . ?
C17 C18 1.388(6) . ?
C17 H21 0.9300 . ?
C18 H22 0.9300 . ?
C19 C20 1.350(5) . ?
C19 C24 1.376(5) . ?
C20 C21 1.368(6) . ?
C20 H23 0.9300 . ?
C21 C22 1.362(6) . ?
C21 H24 0.9300 . ?
C22 C23 1.378(6) . ?
C22 C25 1.496(6) . ?
C23 C24 1.378(6) . ?
C23 H25 0.9300 . ?
C24 H26 0.9300 . ?
C25 H27 0.9600 . ?
C25 H28 0.9600 . ?
C25 H29 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
O6 S O5 119.4(2) . . ?
O6 S N1 105.40(18) . . ?
O5 S N1 110.85(18) . . ?
O6 S C19 110.4(2) . . ?
O5 S C19 108.5(2) . . ?
N1 S C19 100.75(17) . . ?
C2 N1 C1 61.0(2) . . ?
C2 N1 S 117.8(3) . . ?
C1 N1 S 114.0(3) . . ?
C9 O2 C10 104.8(5) . . ?
C11 O4 C12 115.1(3) . . ?
N1 C1 C13 117.2(4) . . ?
N1 C1 C2 58.9(2) . . ?
C13 C1 C2 124.4(4) . . ?
N1 C1 H1 112(2) . . ?
C13 C1 H1 120(2) . . ?
C2 C1 H1 110(2) . . ?
N1 C2 C3 117.2(4) . . ?
N1 C2 C1 60.0(2) . . ?
C3 C2 C1 122.9(4) . . ?
N1 C2 H2 117(2) . . ?
C3 C2 H2 111(2) . . ?
C1 C2 H2 120(2) . . ?
C8 C3 C2 121.0(3) . . ?
C8 C3 C4 122.1(4) . . ?
C2 C3 C4 116.8(4) . . ?
C3 C4 C5 111.8(4) . . ?
C3 C4 H3 110(3) . . ?
C5 C4 H3 110(3) . . ?
C3 C4 H4 111(2) . . ?
C5 C4 H4 109(2) . . ?
H3 C4 H4 106(4) . . ?
C6 C5 C4 113.3(4) . . ?
C6 C5 H6 108.9 . . ?
C4 C5 H6 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
H6 C5 H5 107.7 . . ?
C7 C6 C5 113.9(5) . . ?
C7 C6 H7 108.8 . . ?
C5 C6 H7 108.8 . . ?
C7 C6 H8 108.8 . . ?
C5 C6 H8 108.8 . . ?
H7 C6 H8 107.7 . . ?
C6 C7 H11 109.5 . . ?
C6 C7 H10 109.5 . . ?
H11 C7 H10 109.5 . . ?
C6 C7 H9 109.5 . . ?
H11 C7 H9 109.5 . . ?
H10 C7 H9 109.5 . . ?
C3 C8 C11 123.0(4) . . ?
C3 C8 C9 123.2(4) . . ?
C11 C8 C9 113.7(4) . . ?
O1 C9 O2 126.5(6) . . ?
O1 C9 C8 123.2(5) . . ?
O2 C9 C8 110.2(5) . . ?
O2 C10 H12 109.5 . . ?
O2 C10 H14 109.5 . . ?
H12 C10 H14 109.5 . . ?
O2 C10 H13 109.5 . . ?
H12 C10 H13 109.5 . . ?
H14 C10 H13 109.5 . . ?
O3 C11 O4 124.4(4) . . ?
O3 C11 C8 125.0(4) . . ?
O4 C11 C8 110.6(4) . . ?
O4 C12 H15 109.5 . . ?
O4 C12 H16 109.5 . . ?
H15 C12 H16 109.5 . . ?
O4 C12 H17 109.5 . . ?
H15 C12 H17 109.5 . . ?
H16 C12 H17 109.5 . . ?
C18 C13 C14 118.6(4) . . ?
C18 C13 C1 122.7(4) . . ?
C14 C13 C1 118.7(4) . . ?
C13 C14 C15 121.3(5) . . ?
C13 C14 H18 119.4 . . ?
C15 C14 H18 119.4 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H19 120.4 . . ?
C14 C15 H19 120.4 . . ?
C17 C16 C15 120.6(6) . . ?
C17 C16 H20 119.7 . . ?
C15 C16 H20 119.7 . . ?
C16 C17 C18 120.3(6) . . ?
C16 C17 H21 119.8 . . ?
C18 C17 H21 119.8 . . ?
C13 C18 C17 119.9(5) . . ?
C13 C18 H22 120.0 . . ?
C17 C18 H22 120.0 . . ?
C20 C19 C24 120.0(4) . . ?
C20 C19 S 120.5(4) . . ?
C24 C19 S 119.5(4) . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H23 120.0 . . ?
C21 C20 H23 120.0 . . ?
C22 C21 C20 122.4(4) . . ?
C22 C21 H24 118.8 . . ?
C20 C21 H24 118.8 . . ?
C21 C22 C23 116.9(4) . . ?
C21 C22 C25 122.6(5) . . ?
C23 C22 C25 120.6(5) . . ?
C24 C23 C22 121.9(5) . . ?
C24 C23 H25 119.1 . . ?
C22 C23 H25 119.1 . . ?
C19 C24 C23 119.0(4) . . ?
C19 C24 H26 120.5 . . ?
C23 C24 H26 120.5 . . ?
C22 C25 H27 109.5 . . ?
C22 C25 H28 109.5 . . ?
H27 C25 H28 109.5 . . ?
C22 C25 H29 109.5 . . ?
H27 C25 H29 109.5 . . ?
H28 C25 H29 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
O6 S N1 C2 -152.2(3) . . . . ?
O5 S N1 C2 -21.7(3) . . . . ?
C19 S N1 C2 92.9(3) . . . . ?
O6 S N1 C1 -83.6(3) . . . . ?
O5 S N1 C1 46.9(3) . . . . ?
C19 S N1 C1 161.5(3) . . . . ?
C2 N1 C1 C13 -115.6(4) . . . . ?
S N1 C1 C13 134.7(3) . . . . ?
S N1 C1 C2 -109.7(3) . . . . ?
C1 N1 C2 C3 114.2(4) . . . . ?
S N1 C2 C3 -142.3(3) . . . . ?
S N1 C2 C1 103.6(3) . . . . ?
C13 C1 C2 N1 103.6(5) . . . . ?
N1 C1 C2 C3 -104.8(4) . . . . ?
C13 C1 C2 C3 -1.2(7) . . . . ?
N1 C2 C3 C8 -144.6(4) . . . . ?
C1 C2 C3 C8 -74.3(6) . . . . ?
N1 C2 C3 C4 38.9(5) . . . . ?
C1 C2 C3 C4 109.2(5) . . . . ?
C8 C3 C4 C5 -92.3(6) . . . . ?
C2 C3 C4 C5 84.1(5) . . . . ?
C3 C4 C5 C6 175.6(5) . . . . ?
C4 C5 C6 C7 -175.9(5) . . . . ?
C2 C3 C8 C11 1.1(6) . . . . ?
C4 C3 C8 C11 177.5(4) . . . . ?
C2 C3 C8 C9 -175.9(4) . . . . ?
C4 C3 C8 C9 0.4(7) . . . . ?
C10 O2 C9 O1 10.3(8) . . . . ?
C10 O2 C9 C8 -172.9(4) . . . . ?
C3 C8 C9 O1 91.6(7) . . . . ?
C11 C8 C9 O1 -85.6(6) . . . . ?
C3 C8 C9 O2 -85.3(5) . . . . ?
C11 C8 C9 O2 97.5(5) . . . . ?
C12 O4 C11 O3 0.2(7) . . . . ?
C12 O4 C11 C8 -178.8(4) . . . . ?
C3 C8 C11 O3 -15.3(7) . . . . ?
C9 C8 C11 O3 162.0(4) . . . . ?
C3 C8 C11 O4 163.7(4) . . . . ?
C9 C8 C11 O4 -19.0(5) . . . . ?
N1 C1 C13 C18 -1.4(6) . . . . ?
C2 C1 C13 C18 -70.8(6) . . . . ?
N1 C1 C13 C14 -179.3(3) . . . . ?
C2 C1 C13 C14 111.3(5) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
C1 C13 C14 C15 178.6(4) . . . . ?
C13 C14 C15 C16 -1.3(8) . . . . ?
C14 C15 C16 C17 0.5(9) . . . . ?
C15 C16 C17 C18 0.8(9) . . . . ?
C14 C13 C18 C17 0.8(6) . . . . ?
C1 C13 C18 C17 -177.1(4) . . . . ?
C16 C17 C18 C13 -1.5(7) . . . . ?
O6 S C19 C20 139.8(3) . . . . ?
O5 S C19 C20 7.3(4) . . . . ?
N1 S C19 C20 -109.2(4) . . . . ?
O6 S C19 C24 -40.1(4) . . . . ?
O5 S C19 C24 -172.6(3) . . . . ?
N1 S C19 C24 70.9(4) . . . . ?
C24 C19 C20 C21 0.0(6) . . . . ?
S C19 C20 C21 -179.9(3) . . . . ?
C19 C20 C21 C22 -0.3(7) . . . . ?
C20 C21 C22 C23 0.7(7) . . . . ?
C20 C21 C22 C25 179.2(4) . . . . ?
C21 C22 C23 C24 -0.9(7) . . . . ?
C25 C22 C23 C24 -179.4(4) . . . . ?
C20 C19 C24 C23 -0.2(6) . . . . ?
S C19 C24 C23 179.7(3) . . . . ?
C22 C23 C24 C19 0.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.050

### END