# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Ya Li'
_publ_contact_author_email       ya.li@sues.edu.cn
loop_
_publ_author_name
'Ya Li'
'Zhihua Sun'

data_mo_dm11223_0m
_database_code_depnum_ccdc_archive 'CCDC 830371'
#TrackingRef 'web_deposit_cif_file_0_YaLi_1308295700.mo_dm11223_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 N O3 S2'
_chemical_formula_weight         407.57

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.0665(17)
_cell_length_b                   8.4236(14)
_cell_length_c                   12.792(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.133(3)
_cell_angle_gamma                90.00
_cell_volume                     1078.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5513
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.22

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9123
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      133(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7673
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4587
_reflns_number_gt                4430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0374P)^2^+0.1927P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4587
_refine_ls_number_parameters     249
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
S1 S 0.18676(4) 0.33606(5) 0.48118(3) 0.01648(9) Uani 1 1 d . . .
S2 S 0.33222(4) 0.08406(5) 0.21480(3) 0.01725(9) Uani 1 1 d . . .
O1 O 0.07587(13) 0.42787(15) 0.52101(10) 0.0247(3) Uani 1 1 d . . .
O2 O 0.36304(13) -0.04070(15) 0.14400(11) 0.0265(3) Uani 1 1 d . . .
O3 O 0.40811(11) 0.09545(17) 0.31629(9) 0.0235(3) Uani 1 1 d . . .
N1 N 0.12968(13) 0.18430(17) 0.40658(10) 0.0153(3) Uani 1 1 d . . .
H1 H 0.1125 0.0912 0.4334 0.018 Uiso 1 1 calc R . .
C1 C 0.10980(15) 0.21541(19) 0.29322(12) 0.0142(3) Uani 1 1 d . . .
H1A H 0.1683 0.3075 0.2797 0.017 Uiso 1 1 calc R . .
C2 C 0.15535(14) 0.0742(2) 0.22789(12) 0.0152(3) Uani 1 1 d . . .
H2 H 0.1104 0.0913 0.1552 0.018 Uiso 1 1 calc R . .
C3 C 0.10707(17) -0.0911(2) 0.26107(14) 0.0196(3) Uani 1 1 d . . .
H3 H 0.0229 -0.0721 0.2943 0.023 Uiso 1 1 calc R . .
C4 C 0.0681(2) -0.1957(2) 0.16489(15) 0.0289(4) Uani 1 1 d . . .
H4A H 0.1474 -0.2178 0.1291 0.043 Uiso 1 1 calc R . .
H4B H 0.0013 -0.1406 0.1166 0.043 Uiso 1 1 calc R . .
H4C H 0.0306 -0.2959 0.1874 0.043 Uiso 1 1 calc R . .
C5 C 0.20114(18) -0.1799(2) 0.34298(14) 0.0251(4) Uani 1 1 d . . .
H5A H 0.1573 -0.2768 0.3643 0.038 Uiso 1 1 calc R . .
H5B H 0.2231 -0.1118 0.4045 0.038 Uiso 1 1 calc R . .
H5C H 0.2833 -0.2081 0.3126 0.038 Uiso 1 1 calc R . .
C6 C 0.26353(16) 0.2238(2) 0.59567(13) 0.0197(3) Uani 1 1 d . . .
C7 C 0.3830(2) 0.1326(3) 0.56326(16) 0.0356(5) Uani 1 1 d . . .
H7A H 0.4276 0.0766 0.6244 0.053 Uiso 1 1 calc R . .
H7B H 0.4459 0.2070 0.5361 0.053 Uiso 1 1 calc R . .
H7C H 0.3526 0.0556 0.5084 0.053 Uiso 1 1 calc R . .
C8 C 0.1592(2) 0.1169(2) 0.63620(14) 0.0282(4) Uani 1 1 d . . .
H8A H 0.1421 0.0262 0.5887 0.042 Uiso 1 1 calc R . .
H8B H 0.0763 0.1768 0.6395 0.042 Uiso 1 1 calc R . .
H8C H 0.1918 0.0787 0.7066 0.042 Uiso 1 1 calc R . .
C9 C 0.30974(19) 0.3500(3) 0.67751(13) 0.0289(4) Uani 1 1 d . . .
H9A H 0.2316 0.4010 0.7027 0.043 Uiso 1 1 calc R . .
H9B H 0.3634 0.4300 0.6456 0.043 Uiso 1 1 calc R . .
H9C H 0.3638 0.2999 0.7368 0.043 Uiso 1 1 calc R . .
C10 C -0.03220(15) 0.26045(19) 0.24882(12) 0.0149(3) Uani 1 1 d . . .
C11 C -0.04734(16) 0.3414(2) 0.15343(12) 0.0220(3) Uani 1 1 d . . .
H11 H 0.0295 0.3708 0.1208 0.026 Uiso 1 1 calc R . .
C12 C -0.17374(18) 0.3798(2) 0.10544(13) 0.0264(4) Uani 1 1 d . . .
H12 H -0.1831 0.4355 0.0405 0.032 Uiso 1 1 calc R . .
C13 C -0.28580(16) 0.3366(2) 0.15248(13) 0.0246(3) Uani 1 1 d . . .
H13 H -0.3723 0.3622 0.1197 0.030 Uiso 1 1 calc R . .
C14 C -0.27203(17) 0.2565(2) 0.24674(15) 0.0236(4) Uani 1 1 d . . .
H14 H -0.3492 0.2265 0.2786 0.028 Uiso 1 1 calc R . .
C15 C -0.14509(16) 0.2190(2) 0.29591(13) 0.0191(3) Uani 1 1 d . . .
H15 H -0.1362 0.1651 0.3615 0.023 Uiso 1 1 calc R . .
C16 C 0.34923(16) 0.2685(2) 0.15024(13) 0.0174(3) Uani 1 1 d . . .
C17 C 0.32972(19) 0.2764(3) 0.04149(14) 0.0266(4) Uani 1 1 d . . .
H17 H 0.3077 0.1838 0.0009 0.032 Uiso 1 1 calc R . .
C18 C 0.3429(2) 0.4218(3) -0.00685(16) 0.0343(5) Uani 1 1 d . . .
H18 H 0.3301 0.4290 -0.0814 0.041 Uiso 1 1 calc R . .
C19 C 0.37429(19) 0.5564(3) 0.05201(16) 0.0315(4) Uani 1 1 d . . .
H19 H 0.3818 0.6557 0.0180 0.038 Uiso 1 1 calc R . .
C20 C 0.39505(17) 0.5469(2) 0.16099(15) 0.0249(4) Uani 1 1 d . . .
H20 H 0.4176 0.6394 0.2014 0.030 Uiso 1 1 calc R . .
C21 C 0.38277(16) 0.4025(2) 0.21054(14) 0.0202(3) Uani 1 1 d . . .
H21 H 0.3971 0.3950 0.2850 0.024 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 0.01790(17) 0.01429(18) 0.01672(17) -0.00063(15) -0.00060(13) 0.00019(15)
S2 0.01339(16) 0.01640(19) 0.02279(19) 0.00007(15) 0.00570(13) 0.00170(15)
O1 0.0287(7) 0.0219(7) 0.0225(6) -0.0046(5) -0.0017(5) 0.0116(5)
O2 0.0245(6) 0.0202(7) 0.0377(7) -0.0042(5) 0.0160(5) 0.0020(5)
O3 0.0162(5) 0.0282(7) 0.0258(6) 0.0058(6) 0.0014(4) 0.0016(5)
N1 0.0173(6) 0.0132(7) 0.0152(6) -0.0001(5) 0.0007(5) 0.0004(5)
C1 0.0128(7) 0.0148(7) 0.0150(7) 0.0001(6) 0.0017(6) 0.0003(6)
C2 0.0128(6) 0.0167(8) 0.0165(7) -0.0028(6) 0.0035(5) 0.0010(6)
C3 0.0200(8) 0.0154(8) 0.0247(9) -0.0027(7) 0.0087(7) -0.0020(6)
C4 0.0351(10) 0.0223(10) 0.0305(9) -0.0075(7) 0.0080(8) -0.0073(8)
C5 0.0276(8) 0.0178(9) 0.0311(9) 0.0032(7) 0.0082(7) 0.0027(7)
C6 0.0203(8) 0.0210(9) 0.0166(8) -0.0008(6) -0.0039(6) 0.0058(7)
C7 0.0277(10) 0.0481(13) 0.0292(10) -0.0065(9) -0.0053(8) 0.0191(9)
C8 0.0370(10) 0.0234(10) 0.0230(9) 0.0065(7) -0.0020(7) -0.0016(8)
C9 0.0317(9) 0.0276(10) 0.0243(8) -0.0061(8) -0.0109(7) 0.0044(9)
C10 0.0150(7) 0.0125(7) 0.0169(7) -0.0018(6) 0.0000(6) 0.0017(6)
C11 0.0217(7) 0.0265(8) 0.0183(7) 0.0030(8) 0.0050(6) 0.0066(8)
C12 0.0297(9) 0.0316(11) 0.0173(8) -0.0001(7) -0.0006(7) 0.0128(8)
C13 0.0190(7) 0.0238(8) 0.0291(8) -0.0081(8) -0.0065(6) 0.0062(8)
C14 0.0157(8) 0.0197(9) 0.0355(10) -0.0013(7) 0.0029(7) -0.0004(6)
C15 0.0175(8) 0.0160(8) 0.0239(8) 0.0008(6) 0.0023(6) 0.0009(6)
C16 0.0128(7) 0.0200(8) 0.0205(8) 0.0023(6) 0.0068(6) -0.0002(6)
C17 0.0281(9) 0.0308(10) 0.0216(9) -0.0026(7) 0.0057(7) -0.0051(8)
C18 0.0387(11) 0.0418(12) 0.0227(9) 0.0077(9) 0.0046(8) -0.0054(9)
C19 0.0268(9) 0.0283(11) 0.0400(11) 0.0142(8) 0.0065(8) 0.0013(8)
C20 0.0184(8) 0.0218(10) 0.0353(10) -0.0009(7) 0.0065(7) 0.0011(7)
C21 0.0153(7) 0.0233(8) 0.0228(8) -0.0018(7) 0.0058(6) -0.0007(6)

_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 O1 1.4917(13) . ?
S1 N1 1.6607(14) . ?
S1 C6 1.8426(16) . ?
S2 O3 1.4375(12) . ?
S2 O2 1.4426(13) . ?
S2 C16 1.7765(18) . ?
S2 C2 1.8080(15) . ?
N1 C1 1.4662(19) . ?
N1 H1 0.8800 . ?
C1 C10 1.529(2) . ?
C1 C2 1.551(2) . ?
C1 H1A 1.0000 . ?
C2 C3 1.548(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(2) . ?
C3 C5 1.531(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.516(3) . ?
C6 C7 1.522(2) . ?
C6 C9 1.529(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.387(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 C21 1.388(2) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
O1 S1 N1 111.70(7) . . ?
O1 S1 C6 105.08(7) . . ?
N1 S1 C6 98.72(7) . . ?
O3 S2 O2 119.11(8) . . ?
O3 S2 C16 107.05(8) . . ?
O2 S2 C16 107.91(8) . . ?
O3 S2 C2 110.67(7) . . ?
O2 S2 C2 107.73(8) . . ?
C16 S2 C2 103.19(8) . . ?
C1 N1 S1 115.66(11) . . ?
C1 N1 H1 122.2 . . ?
S1 N1 H1 122.2 . . ?
N1 C1 C10 115.80(13) . . ?
N1 C1 C2 112.26(13) . . ?
C10 C1 C2 107.98(12) . . ?
N1 C1 H1A 106.8 . . ?
C10 C1 H1A 106.8 . . ?
C2 C1 H1A 106.8 . . ?
C3 C2 C1 114.98(12) . . ?
C3 C2 S2 114.06(11) . . ?
C1 C2 S2 111.43(11) . . ?
C3 C2 H2 105.1 . . ?
C1 C2 H2 105.1 . . ?
S2 C2 H2 105.1 . . ?
C4 C3 C5 110.81(15) . . ?
C4 C3 C2 111.02(14) . . ?
C5 C3 C2 115.97(14) . . ?
C4 C3 H3 106.1 . . ?
C5 C3 H3 106.1 . . ?
C2 C3 H3 106.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C8 C6 C7 112.98(17) . . ?
C8 C6 C9 110.47(15) . . ?
C7 C6 C9 110.23(15) . . ?
C8 C6 S1 109.25(11) . . ?
C7 C6 S1 108.61(12) . . ?
C9 C6 S1 104.97(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.09(14) . . ?
C15 C10 C1 123.60(14) . . ?
C11 C10 C1 117.24(14) . . ?
C12 C11 C10 120.68(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.82(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.00(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.44(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.96(16) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C21 121.29(17) . . ?
C17 C16 S2 119.87(14) . . ?
C21 C16 S2 118.84(13) . . ?
C18 C17 C16 118.70(18) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 120.71(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.11(18) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 119.95(18) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 119.24(16) . . ?
C20 C21 H21 120.4 . . ?
C16 C21 H21 120.4 . . ?

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 H1 O1 0.88 2.46 3.1961(18) 141.1 2_546

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.042