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

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Ying-Chun Chen.'
'Wei Du.'
'Zhi-Jun Jia.'
'Kun Jiang.'
'Tian-Yu Liu.'
'Xiao-Feng Xiong.'

_publ_contact_author_name        'Ying-Chun Chen'
_publ_contact_author_email       YCCHENHUAXI@YAHOO.COM.CN

_publ_section_title              
;
Merging Chiral Organocatalysts: Enantioselectivity
and Diastereoselectivity Switchable Direct Vinylogous Mannich Reaction
of Alkylimines
;

# Attachment 'anti-5m.cif'

data_anti-5m
_database_code_depnum_ccdc_archive 'CCDC 745436'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 N3 O2 S3'
_chemical_formula_weight         545.72

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.2353(10)
_cell_length_b                   16.2177(18)
_cell_length_c                   17.641(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2642.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9054
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8849
_exptl_absorpt_correction_T_max  0.9210
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku SPIDER'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21830
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6032
_reflns_number_gt                5855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0450P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6032
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
S1 S 0.67107(5) 0.23015(3) -0.00418(2) 0.02265(10) Uani 1 1 d . . .
S2 S 0.44271(4) 0.40952(2) 0.22575(2) 0.01941(9) Uani 1 1 d . . .
S3 S 0.61848(6) 0.21128(3) 0.40341(2) 0.03267(12) Uani 1 1 d . . .
O1 O 0.53791(14) 0.44491(7) 0.17037(7) 0.0265(3) Uani 1 1 d . . .
O2 O 0.29024(13) 0.42243(7) 0.21676(7) 0.0258(3) Uani 1 1 d . . .
N1 N 0.46215(15) 0.31046(8) 0.22770(8) 0.0188(3) Uani 1 1 d . . .
N2 N 1.19455(15) 0.20967(9) 0.19997(8) 0.0244(3) Uani 1 1 d . . .
N3 N 0.91153(15) 0.39971(9) 0.26472(9) 0.0296(3) Uani 1 1 d . . .
C1 C 0.78293(17) 0.15087(10) 0.02996(9) 0.0191(3) Uani 1 1 d . . .
C2 C 0.81720(18) 0.08469(10) -0.01706(9) 0.0224(3) Uani 1 1 d . . .
H2 H 0.7799 0.0827 -0.0672 0.027 Uiso 1 1 calc R . .
C3 C 0.90486(18) 0.02225(10) 0.00884(10) 0.0244(4) Uani 1 1 d . . .
H3 H 0.9311 -0.0214 -0.0244 0.029 Uiso 1 1 calc R . .
C4 C 0.95582(19) 0.02217(10) 0.08336(10) 0.0231(4) Uani 1 1 d . . .
H4 H 1.0114 -0.0229 0.1018 0.028 Uiso 1 1 calc R . .
C5 C 0.92441(17) 0.08853(10) 0.13006(9) 0.0186(3) Uani 1 1 d . . .
H5 H 0.9596 0.0890 0.1807 0.022 Uiso 1 1 calc R . .
C6 C 0.84171(16) 0.15478(9) 0.10369(8) 0.0162(3) Uani 1 1 d . . .
C7 C 0.82106(16) 0.23005(9) 0.14928(8) 0.0161(3) Uani 1 1 d . . .
C8 C 0.67780(17) 0.27523(9) 0.14800(8) 0.0170(3) Uani 1 1 d . . .
H8 H 0.6994 0.3350 0.1399 0.020 Uiso 1 1 calc R . .
C9 C 0.57739(18) 0.24786(10) 0.08414(9) 0.0218(4) Uani 1 1 d . . .
H9A H 0.5025 0.2907 0.0762 0.026 Uiso 1 1 calc R . .
H9B H 0.5276 0.1964 0.0995 0.026 Uiso 1 1 calc R . .
C10 C 0.60067(15) 0.26732(9) 0.22636(9) 0.0155(3) Uani 1 1 d . . .
H10 H 0.6648 0.2925 0.2657 0.019 Uiso 1 1 calc R . .
C11 C 0.49958(17) 0.44666(9) 0.31472(9) 0.0176(3) Uani 1 1 d . . .
C12 C 0.61804(18) 0.50001(9) 0.31558(9) 0.0209(3) Uani 1 1 d . . .
H12 H 0.6690 0.5113 0.2700 0.025 Uiso 1 1 calc R . .
C13 C 0.66133(18) 0.53645(10) 0.38268(10) 0.0229(4) Uani 1 1 d . . .
H13 H 0.7414 0.5732 0.3828 0.027 Uiso 1 1 calc R . .
C14 C 0.58934(19) 0.51991(10) 0.44975(10) 0.0233(4) Uani 1 1 d . . .
C15 C 0.47295(18) 0.46474(9) 0.44821(10) 0.0212(3) Uani 1 1 d . . .
H15 H 0.4248 0.4522 0.4944 0.025 Uiso 1 1 calc R . .
C16 C 0.42477(18) 0.42745(9) 0.38150(9) 0.0190(3) Uani 1 1 d . . .
C17 C 0.57421(18) 0.17742(9) 0.24793(9) 0.0178(3) Uani 1 1 d . . .
H17A H 0.5043 0.1535 0.2115 0.021 Uiso 1 1 calc R . .
H17B H 0.6664 0.1468 0.2425 0.021 Uiso 1 1 calc R . .
C18 C 0.51679(19) 0.16379(10) 0.32787(10) 0.0260(4) Uani 1 1 d . . .
H18A H 0.5130 0.1037 0.3374 0.031 Uiso 1 1 calc R . .
H18B H 0.4162 0.1848 0.3301 0.031 Uiso 1 1 calc R . .
C19 C 0.7961(2) 0.17320(10) 0.38827(10) 0.0276(4) Uani 1 1 d . . .
C20 C 0.8241(2) 0.09723(10) 0.35465(9) 0.0242(4) Uani 1 1 d . . .
H20 H 0.7459 0.0631 0.3393 0.029 Uiso 1 1 calc R . .
C21 C 0.9644(2) 0.07128(12) 0.34353(10) 0.0312(4) Uani 1 1 d . . .
H21 H 0.9824 0.0200 0.3193 0.037 Uiso 1 1 calc R . .
C22 C 1.0797(2) 0.11946(14) 0.36745(11) 0.0407(5) Uani 1 1 d . . .
H22 H 1.1765 0.1015 0.3598 0.049 Uiso 1 1 calc R . .
C23 C 1.0520(3) 0.19406(14) 0.40264(12) 0.0472(6) Uani 1 1 d . . .
H23 H 1.1303 0.2269 0.4201 0.057 Uiso 1 1 calc R . .
C24 C 0.9112(2) 0.22126(12) 0.41256(11) 0.0388(5) Uani 1 1 d . . .
H24 H 0.8935 0.2730 0.4361 0.047 Uiso 1 1 calc R . .
C25 C 0.93174(17) 0.26244(10) 0.19054(8) 0.0175(3) Uani 1 1 d . . .
C26 C 1.07656(17) 0.23016(10) 0.19389(9) 0.0188(3) Uani 1 1 d . . .
C27 C 0.91764(17) 0.33845(10) 0.23192(9) 0.0206(3) Uani 1 1 d . . .
C28 C 0.6355(2) 0.56049(12) 0.52254(11) 0.0352(5) Uani 1 1 d . . .
H28A H 0.7123 0.5278 0.5463 0.042 Uiso 1 1 calc R . .
H28B H 0.5525 0.5641 0.5570 0.042 Uiso 1 1 calc R . .
H28C H 0.6718 0.6161 0.5118 0.042 Uiso 1 1 calc R . .
C29 C 0.29960(18) 0.36861(10) 0.38483(10) 0.0240(4) Uani 1 1 d . . .
H29A H 0.3305 0.3144 0.3664 0.029 Uiso 1 1 calc R . .
H29B H 0.2206 0.3893 0.3530 0.029 Uiso 1 1 calc R . .
H29C H 0.2659 0.3637 0.4373 0.029 Uiso 1 1 calc R . .
H1N H 0.383(3) 0.2858(15) 0.2203(14) 0.058(7) 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
S1 0.0284(2) 0.0269(2) 0.01262(18) 0.00152(16) -0.00394(16) 0.00077(17)
S2 0.0241(2) 0.01765(19) 0.01648(18) 0.00175(15) -0.00064(16) 0.00490(16)
S3 0.0566(3) 0.0248(2) 0.0166(2) -0.00105(16) 0.0047(2) 0.0105(2)
O1 0.0417(7) 0.0197(6) 0.0182(6) 0.0031(5) 0.0050(5) 0.0014(5)
O2 0.0256(6) 0.0282(6) 0.0236(6) -0.0018(5) -0.0063(5) 0.0117(5)
N1 0.0158(7) 0.0165(7) 0.0242(7) -0.0003(6) -0.0019(6) 0.0014(5)
N2 0.0181(7) 0.0296(8) 0.0254(8) -0.0046(6) -0.0022(6) -0.0009(6)
N3 0.0230(8) 0.0324(8) 0.0333(9) -0.0109(7) 0.0007(7) -0.0030(6)
C1 0.0192(8) 0.0232(8) 0.0148(7) 0.0008(6) 0.0026(6) -0.0060(6)
C2 0.0240(8) 0.0279(9) 0.0154(7) -0.0039(6) 0.0014(6) -0.0071(7)
C3 0.0265(9) 0.0246(9) 0.0221(8) -0.0080(7) 0.0043(7) -0.0033(7)
C4 0.0225(9) 0.0227(8) 0.0241(9) -0.0023(7) 0.0025(7) -0.0006(7)
C5 0.0167(7) 0.0217(8) 0.0174(7) 0.0007(6) 0.0013(6) -0.0022(6)
C6 0.0152(7) 0.0195(8) 0.0139(7) 0.0000(6) 0.0016(6) -0.0037(6)
C7 0.0174(7) 0.0197(7) 0.0111(7) 0.0019(6) 0.0008(6) -0.0019(6)
C8 0.0178(7) 0.0191(8) 0.0141(7) 0.0009(6) -0.0023(6) 0.0013(6)
C9 0.0181(8) 0.0307(9) 0.0166(7) -0.0015(6) -0.0049(6) 0.0044(6)
C10 0.0137(7) 0.0167(7) 0.0162(7) -0.0001(6) -0.0013(6) 0.0011(6)
C11 0.0187(8) 0.0153(8) 0.0189(8) 0.0017(6) 0.0004(6) 0.0033(6)
C12 0.0226(8) 0.0187(8) 0.0216(8) 0.0038(6) 0.0031(7) 0.0031(7)
C13 0.0216(8) 0.0178(8) 0.0293(9) 0.0037(7) -0.0014(7) -0.0006(6)
C14 0.0276(9) 0.0191(8) 0.0231(8) 0.0016(7) -0.0045(7) 0.0011(7)
C15 0.0261(9) 0.0191(8) 0.0184(8) 0.0019(6) 0.0022(7) 0.0007(7)
C16 0.0197(8) 0.0165(8) 0.0207(8) 0.0023(6) 0.0023(7) 0.0027(6)
C17 0.0198(8) 0.0152(7) 0.0185(8) 0.0010(6) -0.0005(6) 0.0011(6)
C18 0.0288(9) 0.0221(9) 0.0270(9) 0.0044(7) 0.0080(7) 0.0037(7)
C19 0.0467(11) 0.0229(9) 0.0131(8) 0.0038(6) -0.0028(8) -0.0042(8)
C20 0.0331(9) 0.0223(8) 0.0171(8) 0.0010(7) -0.0077(7) -0.0020(7)
C21 0.0371(11) 0.0367(11) 0.0197(9) 0.0062(8) 0.0001(8) 0.0038(8)
C22 0.0353(11) 0.0591(14) 0.0277(10) 0.0147(9) 0.0012(9) -0.0083(10)
C23 0.0519(14) 0.0577(14) 0.0319(11) 0.0113(10) -0.0048(11) -0.0331(12)
C24 0.0641(15) 0.0296(10) 0.0226(9) 0.0009(8) -0.0011(9) -0.0176(10)
C25 0.0167(7) 0.0210(8) 0.0146(7) -0.0001(6) 0.0007(6) 0.0016(6)
C26 0.0191(8) 0.0217(8) 0.0157(7) -0.0033(6) 0.0012(6) -0.0039(6)
C27 0.0139(7) 0.0289(9) 0.0190(8) -0.0021(7) -0.0022(6) -0.0018(6)
C28 0.0476(12) 0.0310(10) 0.0268(10) 0.0003(8) -0.0065(9) -0.0081(9)
C29 0.0233(9) 0.0236(8) 0.0252(9) -0.0040(7) 0.0057(7) -0.0036(7)

_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 C1 1.7559(17) . ?
S1 C9 1.8050(17) . ?
S2 O2 1.4324(12) . ?
S2 O1 1.4342(12) . ?
S2 N1 1.6168(14) . ?
S2 C11 1.7612(16) . ?
S3 C19 1.773(2) . ?
S3 C18 1.8031(19) . ?
N1 C10 1.4583(19) . ?
N1 H1N 0.84(2) . ?
N2 C26 1.144(2) . ?
N3 C27 1.151(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.411(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.474(2) . ?
C7 C25 1.360(2) . ?
C7 C8 1.513(2) . ?
C8 C9 1.525(2) . ?
C8 C10 1.560(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C17 1.527(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.395(2) . ?
C11 C16 1.401(2) . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(2) . ?
C14 C28 1.505(2) . ?
C15 C16 1.396(2) . ?
C15 H15 0.9500 . ?
C16 C29 1.500(2) . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.386(3) . ?
C19 C20 1.392(2) . ?
C20 C21 1.377(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.438(2) . ?
C25 C27 1.439(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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 S1 C9 95.88(8) . . ?
O2 S2 O1 117.95(8) . . ?
O2 S2 N1 104.88(7) . . ?
O1 S2 N1 110.12(7) . . ?
O2 S2 C11 109.99(7) . . ?
O1 S2 C11 106.71(7) . . ?
N1 S2 C11 106.72(8) . . ?
C19 S3 C18 102.81(8) . . ?
C10 N1 S2 125.01(11) . . ?
C10 N1 H1N 121.9(17) . . ?
S2 N1 H1N 111.9(17) . . ?
C2 C1 C6 119.76(15) . . ?
C2 C1 S1 119.58(13) . . ?
C6 C1 S1 120.64(12) . . ?
C3 C2 C1 120.23(16) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.81(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.24(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.89(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.84(14) . . ?
C5 C6 C7 121.71(14) . . ?
C1 C6 C7 119.37(14) . . ?
C25 C7 C6 120.96(14) . . ?
C25 C7 C8 118.56(13) . . ?
C6 C7 C8 120.41(13) . . ?
C7 C8 C9 113.69(13) . . ?
C7 C8 C10 110.26(12) . . ?
C9 C8 C10 110.67(13) . . ?
C7 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
C8 C9 S1 113.10(11) . . ?
C8 C9 H9A 109.0 . . ?
S1 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
S1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N1 C10 C17 108.28(12) . . ?
N1 C10 C8 112.05(12) . . ?
C17 C10 C8 111.87(12) . . ?
N1 C10 H10 108.2 . . ?
C17 C10 H10 108.2 . . ?
C8 C10 H10 108.2 . . ?
C12 C11 C16 121.04(15) . . ?
C12 C11 S2 117.11(12) . . ?
C16 C11 S2 121.76(12) . . ?
C13 C12 C11 120.09(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.70(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 118.48(16) . . ?
C13 C14 C28 120.59(16) . . ?
C15 C14 C28 120.93(16) . . ?
C16 C15 C14 122.57(16) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C11 117.10(15) . . ?
C15 C16 C29 119.22(15) . . ?
C11 C16 C29 123.67(15) . . ?
C18 C17 C10 115.17(13) . . ?
C18 C17 H17A 108.5 . . ?
C10 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C10 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 S3 116.17(12) . . ?
C17 C18 H18A 108.2 . . ?
S3 C18 H18A 108.2 . . ?
C17 C18 H18B 108.2 . . ?
S3 C18 H18B 108.2 . . ?
H18A C18 H18B 107.4 . . ?
C24 C19 C20 119.14(19) . . ?
C24 C19 S3 117.85(15) . . ?
C20 C19 S3 123.00(15) . . ?
C21 C20 C19 120.42(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.47(18) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.2(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.15(19) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C7 C25 C26 125.49(14) . . ?
C7 C25 C27 122.30(14) . . ?
C26 C25 C27 112.05(14) . . ?
N2 C26 C25 174.66(17) . . ?
N3 C27 C25 177.58(17) . . ?
C14 C28 H28A 109.5 . . ?
C14 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C14 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C16 C29 H29A 109.5 . . ?
C16 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C16 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S2 N1 C10 171.76(13) . . . . ?
O1 S2 N1 C10 43.90(15) . . . . ?
C11 S2 N1 C10 -71.55(14) . . . . ?
C9 S1 C1 C2 143.44(14) . . . . ?
C9 S1 C1 C6 -38.41(14) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
S1 C1 C2 C3 179.88(13) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C2 C3 C4 C5 -3.9(3) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 3.8(2) . . . . ?
C4 C5 C6 C7 -172.89(14) . . . . ?
C2 C1 C6 C5 -5.0(2) . . . . ?
S1 C1 C6 C5 176.90(12) . . . . ?
C2 C1 C6 C7 171.84(14) . . . . ?
S1 C1 C6 C7 -6.3(2) . . . . ?
C5 C6 C7 C25 39.6(2) . . . . ?
C1 C6 C7 C25 -137.11(16) . . . . ?
C5 C6 C7 C8 -143.42(15) . . . . ?
C1 C6 C7 C8 39.9(2) . . . . ?
C25 C7 C8 C9 163.81(14) . . . . ?
C6 C7 C8 C9 -13.3(2) . . . . ?
C25 C7 C8 C10 -71.24(18) . . . . ?
C6 C7 C8 C10 111.69(15) . . . . ?
C7 C8 C9 S1 -40.43(17) . . . . ?
C10 C8 C9 S1 -165.16(10) . . . . ?
C1 S1 C9 C8 61.39(13) . . . . ?
S2 N1 C10 C17 166.60(12) . . . . ?
S2 N1 C10 C8 -69.56(17) . . . . ?
C7 C8 C10 N1 179.71(12) . . . . ?
C9 C8 C10 N1 -53.63(17) . . . . ?
C7 C8 C10 C17 -58.47(16) . . . . ?
C9 C8 C10 C17 68.19(16) . . . . ?
O2 S2 C11 C12 -128.94(12) . . . . ?
O1 S2 C11 C12 0.10(14) . . . . ?
N1 S2 C11 C12 117.82(13) . . . . ?
O2 S2 C11 C16 47.57(15) . . . . ?
O1 S2 C11 C16 176.61(13) . . . . ?
N1 S2 C11 C16 -65.67(15) . . . . ?
C16 C11 C12 C13 -1.5(2) . . . . ?
S2 C11 C12 C13 174.99(13) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C12 C13 C14 C28 -179.23(16) . . . . ?
C13 C14 C15 C16 -1.6(2) . . . . ?
C28 C14 C15 C16 178.41(16) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C14 C15 C16 C29 179.68(14) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
S2 C11 C16 C15 -175.61(12) . . . . ?
C12 C11 C16 C29 -178.05(14) . . . . ?
S2 C11 C16 C29 5.6(2) . . . . ?
N1 C10 C17 C18 -63.44(18) . . . . ?
C8 C10 C17 C18 172.60(13) . . . . ?
C10 C17 C18 S3 -52.48(18) . . . . ?
C19 S3 C18 C17 -54.45(13) . . . . ?
C18 S3 C19 C24 152.47(14) . . . . ?
C18 S3 C19 C20 -28.73(16) . . . . ?
C24 C19 C20 C21 -2.0(3) . . . . ?
S3 C19 C20 C21 179.23(14) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C19 1.0(3) . . . . ?
C20 C19 C24 C23 0.6(3) . . . . ?
S3 C19 C24 C23 179.49(16) . . . . ?
C6 C7 C25 C26 1.2(2) . . . . ?
C8 C7 C25 C26 -175.89(14) . . . . ?
C6 C7 C25 C27 176.17(14) . . . . ?
C8 C7 C25 C27 -0.9(2) . . . . ?
C7 C25 C26 N2 175.6(18) . . . . ?
C27 C25 C26 N2 0(2) . . . . ?
C7 C25 C27 N3 -152(4) . . . . ?
C26 C25 C27 N3 24(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.84(2) 2.17(2) 3.003(2) 174(2) 1_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042

# Attachment 'syn-4m.cif'

data_syn-4m
_database_code_depnum_ccdc_archive 'CCDC 745437'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H27 N3 O2 S3'
_chemical_formula_sum            'C29 H27 N3 O2 S3'
_chemical_formula_weight         545.72
_chemical_absolute_configuration rmad

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   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb '

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

_cell_length_a                   7.2498(8)
_cell_length_b                   13.0008(15)
_cell_length_c                   14.4114(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.274(3)
_cell_angle_gamma                90.00
_cell_volume                     1358.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4120
_cell_measurement_theta_min      1.4
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16640
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6100
_reflns_number_gt                5447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear(Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'CrystalStructure 3.8'

_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^)+(0.0453P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack H D (1983), 2862 Friedel pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         6100
_refine_ls_number_parameters     340
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
S1 S 1.22938(7) 0.79819(4) 0.59464(4) 0.02984(14) Uani 1 1 d . . .
S2 S 1.05786(7) 1.08769(4) 0.72678(4) 0.02310(12) Uani 1 1 d . . .
S3 S 0.72900(8) 0.85257(4) 0.87240(4) 0.02615(13) Uani 1 1 d . . .
O1 O 1.1928(2) 1.00942(12) 0.74565(12) 0.0328(4) Uani 1 1 d . . .
O2 O 1.1100(2) 1.17935(11) 0.67723(12) 0.0324(4) Uani 1 1 d . . .
N1 N 0.4810(3) 0.60654(15) 0.43783(14) 0.0332(5) Uani 1 1 d . . .
N2 N 0.5259(3) 0.92539(15) 0.39197(14) 0.0301(4) Uani 1 1 d . . .
N3 N 0.8967(3) 1.03438(13) 0.66541(12) 0.0211(4) Uani 1 1 d . . .
C1 C 1.0871(3) 0.88848(17) 0.53132(15) 0.0253(5) Uani 1 1 d . . .
H1A H 1.1377 0.9585 0.5404 0.030 Uiso 1 1 calc R . .
H1B H 1.0946 0.8723 0.4643 0.030 Uiso 1 1 calc R . .
C2 C 0.8849(3) 0.88832(15) 0.56000(14) 0.0189(4) Uani 1 1 d . . .
H2 H 0.8178 0.9377 0.5188 0.023 Uiso 1 1 calc R . .
C3 C 0.8046(3) 0.78219(14) 0.54323(13) 0.0174(4) Uani 1 1 d . . .
C4 C 0.8866(3) 0.69639(16) 0.59497(14) 0.0202(4) Uani 1 1 d . . .
C5 C 1.0767(3) 0.69675(16) 0.61764(16) 0.0248(5) Uani 1 1 d . . .
C6 C 1.1537(3) 0.61304(16) 0.66451(17) 0.0307(5) Uani 1 1 d . . .
H6 H 1.2825 0.6117 0.6769 0.037 Uiso 1 1 calc R . .
C7 C 1.0450(3) 0.53253(18) 0.69294(18) 0.0354(6) Uani 1 1 d . . .
H7 H 1.0993 0.4760 0.7247 0.042 Uiso 1 1 calc R . .
C8 C 0.8561(3) 0.53316(17) 0.67563(16) 0.0300(5) Uani 1 1 d . . .
H8 H 0.7807 0.4786 0.6974 0.036 Uiso 1 1 calc R . .
C9 C 0.7789(3) 0.61381(15) 0.62644(15) 0.0235(5) Uani 1 1 d . . .
H9 H 0.6503 0.6133 0.6137 0.028 Uiso 1 1 calc R . .
C10 C 0.8547(3) 0.92338(14) 0.66223(13) 0.0168(4) Uani 1 1 d . . .
H10 H 0.9414 0.8854 0.7041 0.020 Uiso 1 1 calc R . .
C11 C 0.6553(3) 0.90261(16) 0.69204(14) 0.0197(4) Uani 1 1 d . . .
H11A H 0.5711 0.9390 0.6488 0.024 Uiso 1 1 calc R . .
H11B H 0.6305 0.8280 0.6860 0.024 Uiso 1 1 calc R . .
C12 C 0.6101(3) 0.93566(15) 0.79095(14) 0.0208(4) Uani 1 1 d . . .
H12A H 0.4753 0.9314 0.8011 0.025 Uiso 1 1 calc R . .
H12B H 0.6490 1.0078 0.8008 0.025 Uiso 1 1 calc R . .
C13 C 0.6545(3) 0.89988(16) 0.98101(14) 0.0219(4) Uani 1 1 d . . .
C14 C 0.5379(3) 0.98392(17) 0.99126(16) 0.0266(5) Uani 1 1 d . . .
H14 H 0.4909 1.0186 0.9382 0.032 Uiso 1 1 calc R . .
C15 C 0.4903(3) 1.01702(18) 1.08030(16) 0.0319(5) Uani 1 1 d . . .
H15 H 0.4126 1.0753 1.0875 0.038 Uiso 1 1 calc R . .
C16 C 0.5549(3) 0.96624(19) 1.15748(16) 0.0344(6) Uani 1 1 d . . .
H16 H 0.5216 0.9893 1.2177 0.041 Uiso 1 1 calc R . .
C17 C 0.6692(3) 0.8808(2) 1.14732(16) 0.0339(6) Uani 1 1 d . . .
H17 H 0.7127 0.8451 1.2006 0.041 Uiso 1 1 calc R . .
C18 C 0.7195(3) 0.84793(18) 1.05960(15) 0.0270(5) Uani 1 1 d . . .
H18 H 0.7983 0.7900 1.0528 0.032 Uiso 1 1 calc R . .
C19 C 0.6610(3) 0.77103(14) 0.48229(13) 0.0184(4) Uani 1 1 d . . .
C20 C 0.5682(3) 0.67636(16) 0.45894(14) 0.0232(5) Uani 1 1 d . . .
C21 C 0.5853(3) 0.85760(17) 0.43294(14) 0.0214(4) Uani 1 1 d . . .
C22 C 0.9652(3) 1.12793(15) 0.83490(15) 0.0212(4) Uani 1 1 d . . .
C23 C 0.8347(3) 1.20714(15) 0.83945(15) 0.0233(5) Uani 1 1 d . . .
C24 C 0.7807(3) 1.23971(16) 0.92801(15) 0.0257(5) Uani 1 1 d . . .
H24 H 0.6936 1.2940 0.9327 0.031 Uiso 1 1 calc R . .
C25 C 0.8492(3) 1.19604(17) 1.00950(15) 0.0260(5) Uani 1 1 d . . .
C26 C 0.9735(3) 1.11555(17) 1.00183(17) 0.0295(5) Uani 1 1 d . . .
H26 H 1.0189 1.0831 1.0564 0.035 Uiso 1 1 calc R . .
C27 C 1.0329(3) 1.08155(17) 0.91540(16) 0.0264(5) Uani 1 1 d . . .
H27 H 1.1194 1.0269 0.9112 0.032 Uiso 1 1 calc R . .
C28 C 0.7478(4) 1.25600(19) 0.75525(16) 0.0378(6) Uani 1 1 d . . .
H28A H 0.8444 1.2763 0.7116 0.057 Uiso 1 1 calc R . .
H28B H 0.6776 1.3169 0.7741 0.057 Uiso 1 1 calc R . .
H28C H 0.6647 1.2066 0.7252 0.057 Uiso 1 1 calc R . .
C29 C 0.7897(4) 1.2369(2) 1.10234(16) 0.0359(6) Uani 1 1 d . . .
H29A H 0.6550 1.2426 1.1037 0.054 Uiso 1 1 calc R . .
H29B H 0.8445 1.3050 1.1124 0.054 Uiso 1 1 calc R . .
H29C H 0.8310 1.1900 1.1514 0.054 Uiso 1 1 calc R . .
H1 H 0.826(4) 1.078(2) 0.6370(19) 0.038(7) 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
S1 0.0156(3) 0.0284(3) 0.0455(3) -0.0050(3) 0.0033(2) -0.0005(2)
S2 0.0170(3) 0.0222(2) 0.0300(3) -0.0070(2) 0.0022(2) -0.0014(2)
S3 0.0268(3) 0.0313(3) 0.0204(2) 0.0031(2) 0.0033(2) 0.0088(2)
O1 0.0181(9) 0.0350(9) 0.0454(10) -0.0146(8) -0.0049(7) 0.0063(7)
O2 0.0317(10) 0.0266(8) 0.0392(9) -0.0057(7) 0.0131(8) -0.0103(7)
N1 0.0327(12) 0.0337(11) 0.0333(11) -0.0058(9) -0.0033(9) -0.0086(9)
N2 0.0298(12) 0.0300(10) 0.0304(10) 0.0034(9) -0.0046(9) 0.0005(8)
N3 0.0221(10) 0.0182(8) 0.0230(9) 0.0002(7) -0.0038(7) 0.0017(7)
C1 0.0222(12) 0.0282(10) 0.0256(10) -0.0019(9) 0.0064(9) -0.0022(9)
C2 0.0188(11) 0.0180(9) 0.0199(9) 0.0011(8) 0.0027(8) -0.0010(8)
C3 0.0157(10) 0.0209(9) 0.0156(9) -0.0036(8) 0.0033(8) 0.0004(8)
C4 0.0179(11) 0.0208(9) 0.0218(10) -0.0044(8) -0.0001(8) 0.0028(8)
C5 0.0213(12) 0.0227(10) 0.0305(11) -0.0063(9) 0.0021(9) -0.0006(9)
C6 0.0216(12) 0.0292(12) 0.0412(13) -0.0036(10) -0.0064(10) 0.0060(9)
C7 0.0345(15) 0.0262(11) 0.0453(14) 0.0014(11) -0.0152(11) 0.0063(10)
C8 0.0314(14) 0.0250(11) 0.0337(12) 0.0025(10) -0.0060(10) 0.0002(9)
C9 0.0206(12) 0.0219(11) 0.0278(11) -0.0002(8) -0.0045(9) -0.0006(8)
C10 0.0172(11) 0.0143(8) 0.0189(9) -0.0011(8) 0.0003(8) -0.0002(7)
C11 0.0168(11) 0.0227(9) 0.0195(9) -0.0005(8) 0.0009(8) 0.0009(8)
C12 0.0171(11) 0.0244(10) 0.0209(10) 0.0016(8) 0.0009(8) 0.0026(8)
C13 0.0174(11) 0.0276(10) 0.0207(10) 0.0008(9) -0.0001(8) -0.0042(8)
C14 0.0243(12) 0.0316(11) 0.0240(10) 0.0025(9) 0.0034(9) -0.0026(9)
C15 0.0288(13) 0.0343(12) 0.0327(12) -0.0065(11) 0.0088(10) -0.0072(10)
C16 0.0339(14) 0.0444(14) 0.0249(11) -0.0067(11) 0.0072(10) -0.0195(11)
C17 0.0286(14) 0.0488(15) 0.0242(11) 0.0014(11) -0.0022(10) -0.0130(11)
C18 0.0249(12) 0.0321(11) 0.0241(10) 0.0031(10) -0.0017(9) -0.0027(10)
C19 0.0208(11) 0.0185(9) 0.0161(9) 0.0001(8) 0.0012(8) 0.0004(8)
C20 0.0220(12) 0.0273(11) 0.0205(10) 0.0002(9) 0.0010(9) 0.0023(9)
C21 0.0199(11) 0.0262(10) 0.0181(9) -0.0020(9) -0.0010(8) -0.0020(9)
C22 0.0172(11) 0.0208(9) 0.0254(10) -0.0052(9) -0.0022(8) -0.0025(8)
C23 0.0247(12) 0.0209(10) 0.0242(10) -0.0019(9) -0.0026(9) 0.0005(8)
C24 0.0259(12) 0.0236(10) 0.0278(11) -0.0023(9) 0.0025(9) 0.0021(9)
C25 0.0254(13) 0.0277(10) 0.0249(10) -0.0021(9) 0.0024(9) -0.0075(9)
C26 0.0284(13) 0.0331(12) 0.0272(11) 0.0051(10) -0.0055(9) -0.0043(9)
C27 0.0224(12) 0.0230(10) 0.0338(11) -0.0003(10) -0.0069(9) 0.0009(9)
C28 0.0496(17) 0.0356(12) 0.0284(12) 0.0010(11) 0.0001(11) 0.0229(12)
C29 0.0364(15) 0.0466(14) 0.0245(11) -0.0011(11) 0.0020(10) -0.0057(11)

_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 C5 1.754(2) . ?
S1 C1 1.807(2) . ?
S2 O1 1.4368(16) . ?
S2 O2 1.4407(16) . ?
S2 N3 1.6179(19) . ?
S2 C22 1.778(2) . ?
S3 C13 1.769(2) . ?
S3 C12 1.811(2) . ?
N1 C20 1.146(3) . ?
N2 C21 1.144(3) . ?
N3 C10 1.476(2) . ?
N3 H1 0.87(3) . ?
C1 C2 1.525(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.517(3) . ?
C2 C10 1.559(3) . ?
C2 H2 1.0000 . ?
C3 C19 1.366(3) . ?
C3 C4 1.466(3) . ?
C4 C9 1.404(3) . ?
C4 C5 1.415(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.534(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C21 1.439(3) . ?
C19 C20 1.442(3) . ?
C22 C27 1.395(3) . ?
C22 C23 1.400(3) . ?
C23 C24 1.402(3) . ?
C23 C28 1.505(3) . ?
C24 C25 1.394(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 C29 1.505(3) . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C5 S1 C1 102.99(11) . . ?
O1 S2 O2 119.97(10) . . ?
O1 S2 N3 106.83(9) . . ?
O2 S2 N3 105.89(10) . . ?
O1 S2 C22 107.60(10) . . ?
O2 S2 C22 106.98(10) . . ?
N3 S2 C22 109.27(10) . . ?
C13 S3 C12 102.69(10) . . ?
C10 N3 S2 125.75(16) . . ?
C10 N3 H1 120.5(19) . . ?
S2 N3 H1 113.5(18) . . ?
C2 C1 S1 114.15(14) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 109.09(16) . . ?
C3 C2 C10 111.16(15) . . ?
C1 C2 C10 113.31(17) . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C10 C2 H2 107.7 . . ?
C19 C3 C4 123.51(18) . . ?
C19 C3 C2 119.34(18) . . ?
C4 C3 C2 117.15(17) . . ?
C9 C4 C5 118.07(19) . . ?
C9 C4 C3 121.40(19) . . ?
C5 C4 C3 120.48(19) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 S1 115.25(18) . . ?
C4 C5 S1 125.00(17) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 121.4(2) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
N3 C10 C11 110.99(16) . . ?
N3 C10 C2 106.58(15) . . ?
C11 C10 C2 110.51(16) . . ?
N3 C10 H10 109.6 . . ?
C11 C10 H10 109.6 . . ?
C2 C10 H10 109.6 . . ?
C12 C11 C10 114.76(17) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 S3 109.51(14) . . ?
C11 C12 H12A 109.8 . . ?
S3 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
S3 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C18 119.8(2) . . ?
C14 C13 S3 123.78(17) . . ?
C18 C13 S3 116.44(17) . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C3 C19 C21 121.49(18) . . ?
C3 C19 C20 126.44(19) . . ?
C21 C19 C20 112.06(18) . . ?
N1 C20 C19 173.7(2) . . ?
N2 C21 C19 178.5(2) . . ?
C27 C22 C23 121.0(2) . . ?
C27 C22 S2 117.94(16) . . ?
C23 C22 S2 121.04(17) . . ?
C22 C23 C24 117.1(2) . . ?
C22 C23 C28 123.57(19) . . ?
C24 C23 C28 119.26(19) . . ?
C25 C24 C23 123.0(2) . . ?
C25 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
C26 C25 C24 118.0(2) . . ?
C26 C25 C29 121.8(2) . . ?
C24 C25 C29 120.2(2) . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C22 119.9(2) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S2 N3 C10 22.89(19) . . . . ?
O2 S2 N3 C10 151.86(16) . . . . ?
C22 S2 N3 C10 -93.23(18) . . . . ?
C5 S1 C1 C2 32.21(18) . . . . ?
S1 C1 C2 C3 -60.4(2) . . . . ?
S1 C1 C2 C10 64.05(19) . . . . ?
C1 C2 C3 C19 -118.7(2) . . . . ?
C10 C2 C3 C19 115.62(19) . . . . ?
C1 C2 C3 C4 61.7(2) . . . . ?
C10 C2 C3 C4 -64.0(2) . . . . ?
C19 C3 C4 C9 -34.8(3) . . . . ?
C2 C3 C4 C9 144.74(19) . . . . ?
C19 C3 C4 C5 147.6(2) . . . . ?
C2 C3 C4 C5 -32.8(3) . . . . ?
C9 C4 C5 C6 4.3(3) . . . . ?
C3 C4 C5 C6 -178.1(2) . . . . ?
C9 C4 C5 S1 -173.59(16) . . . . ?
C3 C4 C5 S1 4.1(3) . . . . ?
C1 S1 C5 C6 178.10(17) . . . . ?
C1 S1 C5 C4 -4.0(2) . . . . ?
C4 C5 C6 C7 -3.2(3) . . . . ?
S1 C5 C6 C7 174.81(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 2.4(4) . . . . ?
C7 C8 C9 C4 -1.2(3) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C3 C4 C9 C8 -179.67(19) . . . . ?
S2 N3 C10 C11 121.16(18) . . . . ?
S2 N3 C10 C2 -118.46(17) . . . . ?
C3 C2 C10 N3 -166.96(17) . . . . ?
C1 C2 C10 N3 69.8(2) . . . . ?
C3 C2 C10 C11 -46.3(2) . . . . ?
C1 C2 C10 C11 -169.55(16) . . . . ?
N3 C10 C11 C12 -61.1(2) . . . . ?
C2 C10 C11 C12 -179.16(16) . . . . ?
C10 C11 C12 S3 -69.5(2) . . . . ?
C13 S3 C12 C11 -178.23(14) . . . . ?
C12 S3 C13 C14 -2.2(2) . . . . ?
C12 S3 C13 C18 177.94(16) . . . . ?
C18 C13 C14 C15 1.4(3) . . . . ?
S3 C13 C14 C15 -178.46(17) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
C14 C13 C18 C17 -0.6(3) . . . . ?
S3 C13 C18 C17 179.30(17) . . . . ?
C4 C3 C19 C21 -179.88(18) . . . . ?
C2 C3 C19 C21 0.6(3) . . . . ?
C4 C3 C19 C20 0.0(3) . . . . ?
C2 C3 C19 C20 -179.52(18) . . . . ?
C3 C19 C20 N1 158(2) . . . . ?
C21 C19 C20 N1 -22(2) . . . . ?
C3 C19 C21 N2 122(9) . . . . ?
C20 C19 C21 N2 -58(9) . . . . ?
O1 S2 C22 C27 0.34(19) . . . . ?
O2 S2 C22 C27 -129.81(17) . . . . ?
N3 S2 C22 C27 115.98(17) . . . . ?
O1 S2 C22 C23 177.35(17) . . . . ?
O2 S2 C22 C23 47.2(2) . . . . ?
N3 S2 C22 C23 -67.01(19) . . . . ?
C27 C22 C23 C24 2.1(3) . . . . ?
S2 C22 C23 C24 -174.77(16) . . . . ?
C27 C22 C23 C28 -176.2(2) . . . . ?
S2 C22 C23 C28 6.9(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C28 C23 C24 C25 177.6(2) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C23 C24 C25 C29 178.1(2) . . . . ?
C24 C25 C26 C27 2.1(3) . . . . ?
C29 C25 C26 C27 -177.3(2) . . . . ?
C25 C26 C27 C22 -0.8(3) . . . . ?
C23 C22 C27 C26 -1.4(3) . . . . ?
S2 C22 C27 C26 175.63(17) . . . . ?

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 H1 N1 0.87(3) 2.50(3) 3.249(3) 145(2) 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.052