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

_journal_coden_Cambridge         182

loop_
_publ_author_name
'R Stockman'
'Jean-Chistophe Legeay'
'William Lewis'

_publ_contact_author_name        'R Stockman'
_publ_contact_author_email       ROBERT.STOCKMAN@NOTTINGHAM.AC.UK

_publ_section_title              
;
Combining two-directional synthesis and tandem
reactions : New access to 3,5-disubstituted pyrrolizidines and first
total synthesis of alkaloid cis-223B.
;

# Attachment 'anobnc.cif'

data_anobnc
_database_code_depnum_ccdc_archive 'CCDC 715790'

_refine_special_details          
;
H3 was located in the difference map and its postion was allowed to refine.
A riding model was used for the U~iso~ and the N3-H3 distance was restrained
to 0.91 A/o. All CH~3~ groups were refined as rigid rotors.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H33 N3 O3 S'
_chemical_formula_sum            'C22 H33 N3 O3 S'
_chemical_formula_weight         419.57

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.7854(6)
_cell_length_b                   8.3741(7)
_cell_length_c                   18.0810(14)
_cell_angle_alpha                83.9330(10)
_cell_angle_beta                 78.6570(10)
_cell_angle_gamma                73.4460(10)
_cell_volume                     1106.33(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5244
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.50

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8236
_exptl_absorpt_correction_T_max  0.9100
_exptl_absorpt_process_details   'SADABS 2007/2'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9712
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4910
_reflns_number_gt                4218
_reflns_threshold_expression     >2s(I)

_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ' ?'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_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^)+(0.0519P)^2^+0.3397P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4910
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      5.201
_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 0.9256(7) 0.7090(7) 0.3017(3) 0.0216(11) Uani 1 1 d . . .
C1 C 1.0013(8) 0.7384(8) 0.3667(4) 0.0228(13) Uani 1 1 d . . .
H1A H 1.0722 0.8228 0.3519 0.027 Uiso 1 1 calc R . .
C2 C 1.1275(9) 0.5674(9) 0.3852(4) 0.0292(15) Uani 1 1 d . . .
H2A H 1.2454 0.5459 0.3500 0.035 Uiso 1 1 calc R . .
H2B H 1.1501 0.5590 0.4377 0.035 Uiso 1 1 calc R . .
C3 C 1.0195(10) 0.4466(9) 0.3750(4) 0.0324(16) Uani 1 1 d . . .
H3A H 0.9361 0.4301 0.4223 0.039 Uiso 1 1 calc RD . .
H3B H 1.1024 0.3369 0.3598 0.039 Uiso 1 1 calc R . .
C4 C 0.9118(9) 0.5317(8) 0.3119(4) 0.0273(14) Uani 1 1 d . . .
H4A H 0.7814 0.5315 0.3279 0.033 Uiso 1 1 calc R . .
C5 C 0.9842(10) 0.4606(9) 0.2336(4) 0.0333(16) Uani 1 1 d . . .
H5A H 1.1084 0.3847 0.2313 0.040 Uiso 1 1 calc R . .
H5B H 0.9036 0.3986 0.2211 0.040 Uiso 1 1 calc R . .
C6 C 0.9854(10) 0.6135(10) 0.1798(4) 0.0332(16) Uani 1 1 d . . .
H6A H 1.0753 0.5845 0.1330 0.040 Uiso 1 1 calc R . .
H6B H 0.8636 0.6664 0.1666 0.040 Uiso 1 1 calc R . .
C7 C 1.0399(9) 0.7266(8) 0.2264(4) 0.0244(13) Uani 1 1 d . . .
H7A H 1.1714 0.6809 0.2304 0.029 Uiso 1 1 calc R . .
C8 C 0.8457(9) 0.7974(8) 0.4334(4) 0.0244(13) Uani 1 1 d . . .
H8A H 0.7687 0.7190 0.4420 0.029 Uiso 1 1 calc R . .
H8B H 0.8997 0.7901 0.4792 0.029 Uiso 1 1 calc R . .
C9 C 0.7244(9) 0.9724(8) 0.4242(3) 0.0230(13) Uani 1 1 d . . .
N2 N 0.5946(7) 1.0165(7) 0.3859(3) 0.0230(11) Uani 1 1 d . . .
N3 N 0.5761(8) 0.8874(7) 0.3457(3) 0.0232(11) Uani 1 1 d D . .
H3 H 0.682(11) 0.831(10) 0.320(5) 0.028 Uiso 1 1 d . . .
S1 S 0.4214(2) 0.95500(19) 0.29180(9) 0.0226(5) Uani 1 1 d . . .
O1 O 0.4359(7) 0.8141(6) 0.2496(3) 0.0301(11) Uani 1 1 d . . .
O2 O 0.2509(6) 1.0312(6) 0.3380(3) 0.0291(11) Uani 1 1 d . . .
C10 C 0.4819(8) 1.1129(8) 0.2278(4) 0.0228(13) Uani 1 1 d . . .
C11 C 0.4799(9) 1.2633(8) 0.2550(4) 0.0254(14) Uani 1 1 d . . .
H11A H 0.4449 1.2814 0.3075 0.031 Uiso 1 1 calc R . .
C12 C 0.5293(9) 1.3862(8) 0.2047(4) 0.0278(14) Uani 1 1 d . . .
H12A H 0.5289 1.4884 0.2232 0.033 Uiso 1 1 calc R . .
C13 C 0.5797(9) 1.3620(9) 0.1274(4) 0.0292(15) Uani 1 1 d . . .
C14 C 0.5784(10) 1.2117(9) 0.1012(4) 0.0311(15) Uani 1 1 d . . .
H14A H 0.6105 1.1945 0.0487 0.037 Uiso 1 1 calc R . .
C15 C 0.5307(9) 1.0865(9) 0.1510(4) 0.0275(14) Uani 1 1 d . . .
H15A H 0.5315 0.9840 0.1326 0.033 Uiso 1 1 calc R . .
C16 C 0.7541(10) 1.1051(9) 0.4664(4) 0.0293(15) Uani 1 1 d . . .
H16A H 0.8804 1.1127 0.4490 0.035 Uiso 1 1 calc R . .
H16B H 0.7417 1.0700 0.5208 0.035 Uiso 1 1 calc R . .
C17 C 0.6249(10) 1.2774(9) 0.4575(5) 0.0361(17) Uani 1 1 d . . .
H17A H 0.6458 1.3530 0.4906 0.054 Uiso 1 1 calc R . .
H17B H 0.4990 1.2705 0.4713 0.054 Uiso 1 1 calc R . .
H17C H 0.6467 1.3200 0.4049 0.054 Uiso 1 1 calc R . .
C18 C 0.6391(11) 1.4951(10) 0.0740(5) 0.0402(18) Uani 1 1 d . . .
H18A H 0.6641 1.4603 0.0220 0.060 Uiso 1 1 calc R . .
H18B H 0.7495 1.5115 0.0865 0.060 Uiso 1 1 calc R . .
H18C H 0.5421 1.5999 0.0788 0.060 Uiso 1 1 calc R . .
C19 C 1.0029(9) 0.9096(9) 0.1992(4) 0.0270(14) Uani 1 1 d . . .
H19A H 0.8732 0.9520 0.1940 0.032 Uiso 1 1 calc R . .
H19B H 1.0232 0.9733 0.2383 0.032 Uiso 1 1 calc R . .
C20 C 1.1190(9) 0.9432(9) 0.1249(4) 0.0276(14) Uani 1 1 d . . .
O3 O 1.2282(8) 0.8335(7) 0.0882(3) 0.0409(14) Uani 1 1 d . . .
C21 C 1.0898(11) 1.1248(10) 0.0993(4) 0.0365(17) Uani 1 1 d . . .
H21B H 1.1396 1.1793 0.1328 0.044 Uiso 1 1 calc R . .
H21C H 0.9573 1.1784 0.1052 0.044 Uiso 1 1 calc R . .
C22 C 1.1762(13) 1.1560(11) 0.0181(5) 0.047(2) Uani 1 1 d . . .
H22C H 1.1491 1.2763 0.0058 0.071 Uiso 1 1 calc R . .
H22D H 1.1271 1.1036 -0.0158 0.071 Uiso 1 1 calc R . .
H22A H 1.3083 1.1081 0.0121 0.071 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
N1 0.022(3) 0.024(3) 0.021(3) -0.002(2) -0.004(2) -0.008(2)
C1 0.021(3) 0.026(3) 0.022(3) -0.001(2) -0.004(2) -0.007(2)
C2 0.026(3) 0.030(3) 0.030(3) 0.000(3) -0.009(3) -0.003(3)
C3 0.035(4) 0.025(3) 0.035(4) 0.001(3) -0.006(3) -0.005(3)
C4 0.025(3) 0.024(3) 0.034(4) -0.003(3) -0.005(3) -0.009(3)
C5 0.032(4) 0.031(4) 0.040(4) -0.012(3) -0.008(3) -0.009(3)
C6 0.035(4) 0.040(4) 0.028(4) -0.010(3) -0.006(3) -0.011(3)
C7 0.022(3) 0.029(3) 0.021(3) -0.004(2) -0.002(2) -0.006(3)
C8 0.026(3) 0.027(3) 0.020(3) 0.000(2) -0.005(2) -0.006(3)
C9 0.024(3) 0.027(3) 0.018(3) -0.001(2) 0.000(2) -0.009(3)
N2 0.024(3) 0.025(3) 0.021(3) -0.003(2) -0.002(2) -0.009(2)
N3 0.023(3) 0.022(3) 0.025(3) -0.003(2) -0.005(2) -0.005(2)
S1 0.0215(8) 0.0222(8) 0.0261(9) -0.0008(6) -0.0054(6) -0.0083(6)
O1 0.035(3) 0.026(2) 0.034(3) -0.003(2) -0.010(2) -0.013(2)
O2 0.021(2) 0.030(3) 0.036(3) 0.000(2) -0.0026(19) -0.0084(19)
C10 0.019(3) 0.024(3) 0.026(3) 0.001(2) -0.006(2) -0.006(2)
C11 0.024(3) 0.025(3) 0.027(3) -0.003(3) -0.004(2) -0.005(3)
C12 0.026(3) 0.022(3) 0.036(4) -0.001(3) -0.008(3) -0.007(3)
C13 0.025(3) 0.032(4) 0.033(4) 0.007(3) -0.010(3) -0.010(3)
C14 0.032(4) 0.039(4) 0.024(3) 0.002(3) -0.007(3) -0.012(3)
C15 0.029(3) 0.029(3) 0.027(3) -0.002(3) -0.008(3) -0.009(3)
C16 0.031(4) 0.033(4) 0.026(3) -0.006(3) -0.005(3) -0.011(3)
C17 0.034(4) 0.031(4) 0.045(4) -0.012(3) -0.004(3) -0.012(3)
C18 0.045(4) 0.041(4) 0.039(4) 0.012(3) -0.013(4) -0.021(4)
C19 0.025(3) 0.031(3) 0.022(3) -0.001(3) -0.002(2) -0.005(3)
C20 0.025(3) 0.035(4) 0.022(3) -0.001(3) -0.005(3) -0.009(3)
O3 0.044(3) 0.040(3) 0.028(3) -0.002(2) 0.007(2) -0.005(2)
C21 0.034(4) 0.037(4) 0.037(4) 0.001(3) -0.001(3) -0.012(3)
C22 0.062(6) 0.047(5) 0.037(4) 0.009(4) -0.005(4) -0.027(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
N1 C1 1.485(8) . ?
N1 C7 1.490(8) . ?
N1 C4 1.509(8) . ?
C1 C2 1.535(9) . ?
C1 C8 1.541(9) . ?
C1 H1A 1.0000 . ?
C2 C3 1.534(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.541(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.532(10) . ?
C4 H4A 1.0000 . ?
C5 C6 1.526(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.525(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C19 1.522(9) . ?
C7 H7A 1.0000 . ?
C8 C9 1.513(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.284(8) . ?
C9 C16 1.505(9) . ?
N2 N3 1.419(7) . ?
N3 S1 1.636(6) . ?
N3 H3 0.89(8) . ?
S1 O2 1.436(5) . ?
S1 O1 1.438(5) . ?
S1 C10 1.769(7) . ?
C10 C15 1.389(9) . ?
C10 C11 1.394(9) . ?
C11 C12 1.388(10) . ?
C11 H11A 0.9500 . ?
C12 C13 1.396(10) . ?
C12 H12A 0.9500 . ?
C13 C14 1.394(10) . ?
C13 C18 1.509(10) . ?
C14 C15 1.392(10) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.519(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.514(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O3 1.212(9) . ?
C20 C21 1.508(10) . ?
C21 C22 1.518(11) . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C22 H22C 0.9800 . ?
C22 H22D 0.9800 . ?
C22 H22A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 114.6(5) . . ?
C1 N1 C4 106.9(5) . . ?
C7 N1 C4 107.3(5) . . ?
N1 C1 C2 103.9(5) . . ?
N1 C1 C8 109.8(5) . . ?
C2 C1 C8 111.7(5) . . ?
N1 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
C8 C1 H1A 110.5 . . ?
C3 C2 C1 102.8(5) . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 104.5(5) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C5 105.1(5) . . ?
N1 C4 C3 106.5(5) . . ?
C5 C4 C3 116.3(6) . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C6 C5 C4 104.4(5) . . ?
C6 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C5 102.2(6) . . ?
C7 C6 H6A 111.3 . . ?
C5 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
N1 C7 C19 110.1(5) . . ?
N1 C7 C6 101.7(5) . . ?
C19 C7 C6 116.1(6) . . ?
N1 C7 H7A 109.6 . . ?
C19 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C9 C8 C1 116.0(5) . . ?
C9 C8 H8A 108.3 . . ?
C1 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N2 C9 C16 117.2(6) . . ?
N2 C9 C8 125.8(6) . . ?
C16 C9 C8 116.9(6) . . ?
C9 N2 N3 114.7(5) . . ?
N2 N3 S1 112.4(4) . . ?
N2 N3 H3 113(5) . . ?
S1 N3 H3 112(5) . . ?
O2 S1 O1 119.3(3) . . ?
O2 S1 N3 108.7(3) . . ?
O1 S1 N3 104.7(3) . . ?
O2 S1 C10 107.1(3) . . ?
O1 S1 C10 108.3(3) . . ?
N3 S1 C10 108.3(3) . . ?
C15 C10 C11 120.6(6) . . ?
C15 C10 S1 119.9(5) . . ?
C11 C10 S1 119.5(5) . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C13 121.0(6) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C14 C13 C12 118.7(6) . . ?
C14 C13 C18 121.2(7) . . ?
C12 C13 C18 120.1(7) . . ?
C15 C14 C13 121.0(6) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C10 C15 C14 119.3(6) . . ?
C10 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C9 C16 C17 114.9(6) . . ?
C9 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C9 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C7 114.6(6) . . ?
C20 C19 H19A 108.6 . . ?
C7 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C7 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
O3 C20 C21 121.9(6) . . ?
O3 C20 C19 123.1(7) . . ?
C21 C20 C19 115.1(6) . . ?
C20 C21 C22 114.6(7) . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21C 108.6 . . ?
C22 C21 H21C 108.6 . . ?
H21B C21 H21C 107.6 . . ?
C21 C22 H22C 109.5 . . ?
C21 C22 H22D 109.5 . . ?
H22C C22 H22D 109.5 . . ?
C21 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22D C22 H22A 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
C7 N1 C1 C2 -86.6(6) . . . . ?
C4 N1 C1 C2 32.2(6) . . . . ?
C7 N1 C1 C8 153.9(5) . . . . ?
C4 N1 C1 C8 -87.4(6) . . . . ?
N1 C1 C2 C3 -39.7(6) . . . . ?
C8 C1 C2 C3 78.5(7) . . . . ?
C1 C2 C3 C4 31.9(7) . . . . ?
C1 N1 C4 C5 -135.9(5) . . . . ?
C7 N1 C4 C5 -12.6(7) . . . . ?
C1 N1 C4 C3 -12.0(7) . . . . ?
C7 N1 C4 C3 111.4(6) . . . . ?
C2 C3 C4 N1 -12.9(7) . . . . ?
C2 C3 C4 C5 103.8(7) . . . . ?
N1 C4 C5 C6 -15.1(7) . . . . ?
C3 C4 C5 C6 -132.6(6) . . . . ?
C4 C5 C6 C7 36.4(7) . . . . ?
C1 N1 C7 C19 -82.8(6) . . . . ?
C4 N1 C7 C19 158.7(5) . . . . ?
C1 N1 C7 C6 153.6(5) . . . . ?
C4 N1 C7 C6 35.1(6) . . . . ?
C5 C6 C7 N1 -43.8(6) . . . . ?
C5 C6 C7 C19 -163.2(6) . . . . ?
N1 C1 C8 C9 -71.5(7) . . . . ?
C2 C1 C8 C9 173.9(5) . . . . ?
C1 C8 C9 N2 79.2(8) . . . . ?
C1 C8 C9 C16 -103.4(7) . . . . ?
C16 C9 N2 N3 178.4(5) . . . . ?
C8 C9 N2 N3 -4.2(9) . . . . ?
C9 N2 N3 S1 -174.7(5) . . . . ?
N2 N3 S1 O2 -57.8(5) . . . . ?
N2 N3 S1 O1 173.6(4) . . . . ?
N2 N3 S1 C10 58.2(5) . . . . ?
O2 S1 C10 C15 -129.4(5) . . . . ?
O1 S1 C10 C15 0.5(6) . . . . ?
N3 S1 C10 C15 113.5(6) . . . . ?
O2 S1 C10 C11 50.5(6) . . . . ?
O1 S1 C10 C11 -179.6(5) . . . . ?
N3 S1 C10 C11 -66.6(6) . . . . ?
C15 C10 C11 C12 -0.8(10) . . . . ?
S1 C10 C11 C12 179.3(5) . . . . ?
C10 C11 C12 C13 0.5(10) . . . . ?
C11 C12 C13 C14 0.4(10) . . . . ?
C11 C12 C13 C18 -177.9(6) . . . . ?
C12 C13 C14 C15 -1.0(10) . . . . ?
C18 C13 C14 C15 177.3(7) . . . . ?
C11 C10 C15 C14 0.2(10) . . . . ?
S1 C10 C15 C14 -179.9(5) . . . . ?
C13 C14 C15 C10 0.7(10) . . . . ?
N2 C9 C16 C17 -0.4(9) . . . . ?
C8 C9 C16 C17 -178.1(6) . . . . ?
N1 C7 C19 C20 177.1(5) . . . . ?
C6 C7 C19 C20 -68.2(8) . . . . ?
C7 C19 C20 O3 2.6(10) . . . . ?
C7 C19 C20 C21 -177.2(6) . . . . ?
O3 C20 C21 C22 12.3(11) . . . . ?
C19 C20 C21 C22 -168.0(7) . . . . ?

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 H3 N1 0.89(8) 1.86(8) 2.711(8) 159(7) .

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.045