# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email duan_shuwen@163.com _publ_author_name 'Wen-Jing Xiao' data_mo_111111a_0m _database_code_depnum_ccdc_archive 'CCDC 861216' #TrackingRef 'mo_111111a_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34 N2 O8 S2' _chemical_formula_weight 614.71 _chemical_absolute_configuration ' unk ' 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+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.6237(6) _cell_length_b 11.9478(7) _cell_length_c 12.4395(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1430.32(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9417 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 32.09 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9646 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 13344 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4167 _reflns_number_gt 3976 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0428P)^2^+0.0187P] 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 -0.06(4) _refine_ls_number_reflns 4167 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0637 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _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 C1 C 0.59164(10) 0.56275(8) 0.38003(8) 0.01435(17) Uani 1 1 d . . . C2 C 0.54448(9) 0.51157(8) 0.28570(8) 0.01301(17) Uani 1 1 d . . . C3 C 0.63143(10) 0.43817(9) 0.23235(9) 0.01743(19) Uani 1 1 d . . . H3 H 0.6025 0.4035 0.1693 0.021 Uiso 1 1 calc R . . C4 C 0.76399(11) 0.41669(9) 0.27457(9) 0.0215(2) Uani 1 1 d . . . H4 H 0.8232 0.3676 0.2390 0.026 Uiso 1 1 calc R . . C5 C 0.80779(10) 0.46776(10) 0.36866(9) 0.0224(2) Uani 1 1 d . . . H5 H 0.8958 0.4520 0.3957 0.027 Uiso 1 1 calc R . . C6 C 0.72185(10) 0.54244(9) 0.42345(9) 0.0199(2) Uani 1 1 d . . . H6 H 0.7507 0.5772 0.4865 0.024 Uiso 1 1 calc R . . C7 C 0.37314(9) 0.63318(8) 0.35812(8) 0.01294(17) Uani 1 1 d . . . C8 C 0.39547(9) 0.54817(8) 0.26723(8) 0.01170(16) Uani 1 1 d . . . C9 C 0.50137(12) 0.69766(10) 0.51984(8) 0.0211(2) Uani 1 1 d . . . H9A H 0.4237 0.7475 0.5268 0.032 Uiso 1 1 calc R . . H9B H 0.5860 0.7402 0.5184 0.032 Uiso 1 1 calc R . . H9C H 0.5031 0.6472 0.5798 0.032 Uiso 1 1 calc R . . C10 C 0.29235(9) 0.44823(8) 0.28081(8) 0.01329(18) Uani 1 1 d . . . H10 H 0.3156 0.4037 0.3445 0.016 Uiso 1 1 calc R . . C11 C 0.30648(11) 0.37882(8) 0.17896(8) 0.01643(18) Uani 1 1 d . . . H11A H 0.2246 0.3328 0.1685 0.020 Uiso 1 1 calc R . . H11B H 0.3871 0.3303 0.1835 0.020 Uiso 1 1 calc R . . C12 C 0.35481(9) 0.59706(8) 0.15765(7) 0.01298(17) Uani 1 1 d . . . H12 H 0.2656 0.6355 0.1666 0.016 Uiso 1 1 calc R . . C13 C 0.45577(10) 0.68012(8) 0.11026(8) 0.01370(17) Uani 1 1 d . . . C14 C 0.49736(11) 0.79619(9) -0.04086(8) 0.01878(19) Uani 1 1 d . . . H14A H 0.5940 0.7736 -0.0459 0.023 Uiso 1 1 calc R . . H14B H 0.4923 0.8652 0.0001 0.023 Uiso 1 1 calc R . . C15 C 0.43700(12) 0.81280(11) -0.15116(9) 0.0268(2) Uani 1 1 d . . . H15A H 0.4444 0.7444 -0.1913 0.040 Uiso 1 1 calc R . . H15B H 0.4871 0.8710 -0.1877 0.040 Uiso 1 1 calc R . . H15C H 0.3410 0.8336 -0.1450 0.040 Uiso 1 1 calc R . . N1 N 0.48843(8) 0.63442(7) 0.42107(7) 0.01512(16) Uani 1 1 d . . . O1 O 0.26730(7) 0.68796(6) 0.37348(6) 0.01755(15) Uani 1 1 d . . . O2 O 0.15217(7) 0.48634(6) 0.28539(6) 0.01718(14) Uani 1 1 d . . . H2 H 0.1462 0.5381 0.3285 0.026 Uiso 1 1 calc R . . O3 O 0.55572(8) 0.71778(7) 0.15584(6) 0.02177(16) Uani 1 1 d . . . O4 O 0.41544(7) 0.70883(6) 0.01111(6) 0.01744(15) Uani 1 1 d . . . S1 S 0.32592(3) 0.47801(2) 0.067953(19) 0.01819(6) Uani 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 C1 0.0135(4) 0.0153(4) 0.0143(4) 0.0018(3) 0.0000(3) -0.0013(3) C2 0.0119(4) 0.0131(4) 0.0141(4) 0.0018(3) 0.0004(3) -0.0001(3) C3 0.0160(4) 0.0168(4) 0.0195(5) -0.0003(4) 0.0019(4) 0.0015(3) C4 0.0152(4) 0.0213(5) 0.0280(5) 0.0024(4) 0.0042(4) 0.0048(4) C5 0.0121(4) 0.0264(5) 0.0288(5) 0.0080(4) -0.0023(4) 0.0012(4) C6 0.0152(4) 0.0245(5) 0.0198(5) 0.0025(4) -0.0037(4) -0.0025(3) C7 0.0149(4) 0.0108(4) 0.0131(4) 0.0013(3) 0.0014(3) -0.0020(3) C8 0.0112(4) 0.0124(4) 0.0115(4) 0.0000(3) -0.0006(3) -0.0005(3) C9 0.0241(5) 0.0242(5) 0.0149(5) -0.0065(4) 0.0001(4) -0.0053(4) C10 0.0127(4) 0.0127(4) 0.0144(4) 0.0012(3) -0.0019(3) -0.0011(3) C11 0.0203(4) 0.0137(4) 0.0153(4) 0.0004(3) -0.0019(4) -0.0030(3) C12 0.0139(4) 0.0127(4) 0.0123(4) 0.0013(3) -0.0015(3) -0.0013(3) C13 0.0155(4) 0.0126(4) 0.0130(4) 0.0003(3) 0.0010(3) -0.0001(3) C14 0.0216(4) 0.0158(4) 0.0190(5) 0.0043(4) 0.0020(4) -0.0050(4) C15 0.0265(5) 0.0317(6) 0.0222(5) 0.0125(5) -0.0010(4) -0.0062(5) N1 0.0150(4) 0.0161(4) 0.0143(4) -0.0028(3) -0.0001(3) -0.0018(3) O1 0.0169(3) 0.0162(3) 0.0195(3) 0.0007(3) 0.0033(3) 0.0030(3) O2 0.0114(3) 0.0189(3) 0.0212(4) 0.0011(3) -0.0009(2) -0.0011(3) O3 0.0239(4) 0.0204(4) 0.0210(4) 0.0022(3) -0.0053(3) -0.0086(3) O4 0.0192(3) 0.0189(3) 0.0142(3) 0.0055(3) -0.0012(3) -0.0052(3) S1 0.02654(12) 0.01566(11) 0.01236(11) 0.00012(9) -0.00323(9) -0.00582(9) _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 C1 C6 1.3860(13) . ? C1 C2 1.3989(14) . ? C1 N1 1.4073(13) . ? C2 C3 1.3819(14) . ? C2 C8 1.5167(13) . ? C3 C4 1.4032(14) . ? C3 H3 0.9300 . ? C4 C5 1.3856(17) . ? C4 H4 0.9300 . ? C5 C6 1.3945(15) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.2257(12) . ? C7 N1 1.3580(12) . ? C7 C8 1.5349(13) . ? C8 C12 1.5338(13) . ? C8 C10 1.5618(13) . ? C9 N1 1.4477(13) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O2 1.4249(11) . ? C10 C11 1.5203(14) . ? C10 H10 0.9800 . ? C11 S1 1.8293(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.5088(13) . ? C12 S1 1.8290(10) . ? C12 H12 0.9800 . ? C13 O3 1.2039(12) . ? C13 O4 1.3377(12) . ? C14 O4 1.4591(12) . ? C14 C15 1.5032(15) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O2 H2 0.8200 . ? 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 C6 C1 C2 122.94(9) . . ? C6 C1 N1 127.11(9) . . ? C2 C1 N1 109.96(8) . . ? C3 C2 C1 118.93(9) . . ? C3 C2 C8 133.06(9) . . ? C1 C2 C8 107.92(8) . . ? C2 C3 C4 119.13(10) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.81(10) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.94(9) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 117.24(10) . . ? C1 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? O1 C7 N1 125.67(9) . . ? O1 C7 C8 125.77(8) . . ? N1 C7 C8 108.52(8) . . ? C2 C8 C12 119.05(8) . . ? C2 C8 C7 102.22(7) . . ? C12 C8 C7 111.52(8) . . ? C2 C8 C10 111.35(7) . . ? C12 C8 C10 103.01(7) . . ? C7 C8 C10 109.71(7) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C11 107.00(8) . . ? O2 C10 C8 111.20(8) . . ? C11 C10 C8 105.67(8) . . ? O2 C10 H10 110.9 . . ? C11 C10 H10 110.9 . . ? C8 C10 H10 110.9 . . ? C10 C11 S1 106.55(6) . . ? C10 C11 H11A 110.4 . . ? S1 C11 H11A 110.4 . . ? C10 C11 H11B 110.4 . . ? S1 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C13 C12 C8 115.68(8) . . ? C13 C12 S1 111.78(7) . . ? C8 C12 S1 106.55(6) . . ? C13 C12 H12 107.5 . . ? C8 C12 H12 107.5 . . ? S1 C12 H12 107.5 . . ? O3 C13 O4 124.77(9) . . ? O3 C13 C12 125.20(9) . . ? O4 C13 C12 110.00(8) . . ? O4 C14 C15 106.86(8) . . ? O4 C14 H14A 110.3 . . ? C15 C14 H14A 110.3 . . ? O4 C14 H14B 110.3 . . ? C15 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 N1 C1 111.15(8) . . ? C7 N1 C9 124.43(9) . . ? C1 N1 C9 124.38(9) . . ? C10 O2 H2 109.5 . . ? C13 O4 C14 115.80(8) . . ? C12 S1 C11 93.37(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.64(15) . . . . ? N1 C1 C2 C3 179.61(9) . . . . ? C6 C1 C2 C8 176.46(9) . . . . ? N1 C1 C2 C8 -3.29(11) . . . . ? C1 C2 C3 C4 0.33(15) . . . . ? C8 C2 C3 C4 -175.89(10) . . . . ? C2 C3 C4 C5 0.22(16) . . . . ? C3 C4 C5 C6 -0.49(17) . . . . ? C2 C1 C6 C5 0.37(15) . . . . ? N1 C1 C6 C5 -179.93(10) . . . . ? C4 C5 C6 C1 0.20(16) . . . . ? C3 C2 C8 C12 -55.45(14) . . . . ? C1 C2 C8 C12 128.03(9) . . . . ? C3 C2 C8 C7 -178.80(11) . . . . ? C1 C2 C8 C7 4.68(10) . . . . ? C3 C2 C8 C10 64.12(14) . . . . ? C1 C2 C8 C10 -112.40(9) . . . . ? O1 C7 C8 C2 177.67(9) . . . . ? N1 C7 C8 C2 -4.60(10) . . . . ? O1 C7 C8 C12 49.39(13) . . . . ? N1 C7 C8 C12 -132.88(8) . . . . ? O1 C7 C8 C10 -64.08(12) . . . . ? N1 C7 C8 C10 113.65(8) . . . . ? C2 C8 C10 O2 168.05(8) . . . . ? C12 C8 C10 O2 -63.24(9) . . . . ? C7 C8 C10 O2 55.63(10) . . . . ? C2 C8 C10 C11 -76.19(9) . . . . ? C12 C8 C10 C11 52.52(9) . . . . ? C7 C8 C10 C11 171.38(8) . . . . ? O2 C10 C11 S1 79.74(8) . . . . ? C8 C10 C11 S1 -38.85(8) . . . . ? C2 C8 C12 C13 -43.60(12) . . . . ? C7 C8 C12 C13 75.05(10) . . . . ? C10 C8 C12 C13 -167.36(8) . . . . ? C2 C8 C12 S1 81.32(9) . . . . ? C7 C8 C12 S1 -160.04(6) . . . . ? C10 C8 C12 S1 -42.44(8) . . . . ? C8 C12 C13 O3 -7.61(14) . . . . ? S1 C12 C13 O3 -129.78(9) . . . . ? C8 C12 C13 O4 174.44(8) . . . . ? S1 C12 C13 O4 52.26(9) . . . . ? O1 C7 N1 C1 -179.35(9) . . . . ? C8 C7 N1 C1 2.92(11) . . . . ? O1 C7 N1 C9 2.99(16) . . . . ? C8 C7 N1 C9 -174.74(9) . . . . ? C6 C1 N1 C7 -179.52(10) . . . . ? C2 C1 N1 C7 0.22(11) . . . . ? C6 C1 N1 C9 -1.86(16) . . . . ? C2 C1 N1 C9 177.88(9) . . . . ? O3 C13 O4 C14 -3.02(14) . . . . ? C12 C13 O4 C14 174.95(8) . . . . ? C15 C14 O4 C13 178.53(9) . . . . ? C13 C12 S1 C11 145.62(7) . . . . ? C8 C12 S1 C11 18.35(7) . . . . ? C10 C11 S1 C12 12.08(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.270 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.052