# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Organic Letters' _journal_coden_cambridge 1336 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Craig Forsyth' _publ_contact_author_email Craig.Forsyth@sci.monash.edu.au loop_ _publ_author_name 'S. V. Bhosale' 'C. M. Forsyth' 'K. P. Ghiggino' 'J. A. Hutchinson' 'C. H. Jani' 'S. J. Langford' 'M. A. P. Lee' 'C. P. Woodward' data_a52_07 _database_code_depnum_ccdc_archive 'CCDC 665869' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H34 N2 O12 S2' _chemical_formula_sum 'C36 H34 N2 O12 S2' _chemical_formula_weight 750.77 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 4.8437(4) _cell_length_b 7.3713(8) _cell_length_c 23.573(2) _cell_angle_alpha 95.651(5) _cell_angle_beta 95.316(5) _cell_angle_gamma 93.561(5) _cell_volume 831.82(14) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 X8 Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12574 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3811 _reflns_number_gt 3390 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2 v2.0 (Bruker AXS, 2005)' _computing_cell_refinement 'Bruker Apex2 v2.0 (Bruker AXS, 2005)' _computing_data_reduction 'Bruker Apex2 v2.0 (Bruker AXS, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0395P)^2^+0.4496P] 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_number_reflns 3811 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.75901(8) 0.74675(6) 0.671953(18) 0.02571(12) Uani 1 1 d . . . O1 O 1.5426(2) 1.14957(15) 0.92342(5) 0.0242(2) Uani 1 1 d . . . O2 O 1.3503(2) 1.69548(15) 0.86026(5) 0.0241(2) Uani 1 1 d . . . O3 O 1.2086(2) 1.18111(14) 0.78703(5) 0.0213(2) Uani 1 1 d . . . O4 O 0.9815(2) 0.89565(15) 0.70397(5) 0.0240(2) Uani 1 1 d . . . O5 O 0.6162(3) 0.84236(18) 0.62995(6) 0.0394(3) Uani 1 1 d . . . O6 O 0.6118(3) 0.66371(17) 0.71347(6) 0.0357(3) Uani 1 1 d . . . N1 N 1.4355(3) 1.41868(17) 0.88965(5) 0.0180(3) Uani 1 1 d . . . C1 C 1.4154(3) 1.2868(2) 0.92787(6) 0.0177(3) Uani 1 1 d . . . C2 C 1.2324(3) 1.32291(19) 0.97456(6) 0.0161(3) Uani 1 1 d . . . C3 C 1.0883(3) 1.48433(19) 0.97814(6) 0.0154(3) Uani 1 1 d . . . C4 C 1.1210(3) 1.61527(19) 0.93920(6) 0.0164(3) Uani 1 1 d . . . C5 C 1.3085(3) 1.5844(2) 0.89359(6) 0.0182(3) Uani 1 1 d . . . C6 C 1.2013(3) 1.1987(2) 1.01379(6) 0.0180(3) Uani 1 1 d . . . H6 H 1.3010 1.0917 1.0117 0.022 Uiso 1 1 calc R . . C7 C 0.9768(3) 1.7709(2) 0.94312(6) 0.0185(3) Uani 1 1 d . . . H7 H 0.9983 1.8581 0.9165 0.022 Uiso 1 1 calc R . . C8 C 1.5926(3) 1.3817(2) 0.83943(6) 0.0213(3) Uani 1 1 d . . . H8A H 1.7094 1.2782 0.8452 0.026 Uiso 1 1 calc R . . H8B H 1.7168 1.4904 0.8354 0.026 Uiso 1 1 calc R . . C9 C 1.3950(3) 1.3356(2) 0.78511(6) 0.0227(3) Uani 1 1 d . . . H9A H 1.2864 1.4424 0.7786 0.027 Uiso 1 1 calc R . . H9B H 1.5056 1.3129 0.7522 0.027 Uiso 1 1 calc R . . C10 C 1.3352(3) 1.0126(2) 0.77713(7) 0.0212(3) Uani 1 1 d . . . H10A H 1.4472 0.9872 0.8124 0.025 Uiso 1 1 calc R . . H10B H 1.4601 1.0202 0.7464 0.025 Uiso 1 1 calc R . . C11 C 1.1118(3) 0.8626(2) 0.75999(6) 0.0214(3) Uani 1 1 d . . . H11A H 1.1924 0.7423 0.7578 0.026 Uiso 1 1 calc R . . H11B H 0.9732 0.8640 0.7883 0.026 Uiso 1 1 calc R . . C12 C 0.9494(3) 0.5808(2) 0.63785(7) 0.0219(3) Uani 1 1 d . . . C13 C 0.9744(4) 0.4133(2) 0.65884(7) 0.0274(4) Uani 1 1 d . . . H13 H 0.8925 0.3878 0.6926 0.033 Uiso 1 1 calc R . . C14 C 1.1202(4) 0.2826(2) 0.63022(7) 0.0298(4) Uani 1 1 d . . . H14 H 1.1381 0.1676 0.6447 0.036 Uiso 1 1 calc R . . C15 C 1.2403(3) 0.3175(2) 0.58081(7) 0.0284(4) Uani 1 1 d . . . C16 C 1.2123(4) 0.4870(2) 0.56104(7) 0.0300(4) Uani 1 1 d . . . H16 H 1.2949 0.5132 0.5275 0.036 Uiso 1 1 calc R . . C17 C 1.0679(3) 0.6191(2) 0.58880(7) 0.0277(4) Uani 1 1 d . . . H17 H 1.0502 0.7343 0.5744 0.033 Uiso 1 1 calc R . . C18 C 1.3941(4) 0.1753(3) 0.54892(9) 0.0425(5) Uani 1 1 d . . . H18A H 1.3976 0.0659 0.5694 0.064 Uiso 1 1 calc R . . H18B H 1.5849 0.2239 0.5463 0.064 Uiso 1 1 calc R . . H18C H 1.2998 0.1434 0.5103 0.064 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 0.0209(2) 0.0231(2) 0.0311(2) -0.00437(16) 0.00054(16) -0.00052(15) O1 0.0283(6) 0.0202(6) 0.0249(6) 0.0014(4) 0.0036(4) 0.0093(5) O2 0.0318(6) 0.0198(6) 0.0214(5) 0.0045(4) 0.0050(5) 0.0005(5) O3 0.0239(5) 0.0150(5) 0.0241(5) -0.0015(4) 0.0023(4) 0.0012(4) O4 0.0283(6) 0.0192(5) 0.0231(5) 0.0008(4) 0.0003(4) -0.0035(4) O5 0.0348(7) 0.0347(7) 0.0447(8) -0.0045(6) -0.0134(6) 0.0105(6) O6 0.0290(6) 0.0293(7) 0.0479(8) -0.0073(6) 0.0158(6) -0.0064(5) N1 0.0197(6) 0.0172(6) 0.0166(6) 0.0004(5) 0.0015(5) 0.0011(5) C1 0.0178(7) 0.0158(7) 0.0180(7) -0.0007(5) -0.0026(5) 0.0003(5) C2 0.0155(6) 0.0147(7) 0.0171(7) -0.0002(5) -0.0023(5) 0.0005(5) C3 0.0148(6) 0.0127(7) 0.0170(7) -0.0002(5) -0.0035(5) -0.0011(5) C4 0.0167(7) 0.0149(7) 0.0163(6) -0.0001(5) -0.0024(5) -0.0011(5) C5 0.0190(7) 0.0162(7) 0.0177(7) -0.0007(6) -0.0014(5) -0.0021(5) C6 0.0191(7) 0.0131(7) 0.0209(7) 0.0006(5) -0.0027(5) 0.0024(5) C7 0.0218(7) 0.0142(7) 0.0189(7) 0.0030(5) -0.0019(6) 0.0000(6) C8 0.0219(7) 0.0206(7) 0.0208(7) -0.0011(6) 0.0051(6) -0.0011(6) C9 0.0332(8) 0.0162(7) 0.0181(7) 0.0000(6) 0.0034(6) -0.0013(6) C10 0.0211(7) 0.0162(7) 0.0259(8) 0.0006(6) 0.0010(6) 0.0027(6) C11 0.0250(8) 0.0179(7) 0.0213(7) 0.0031(6) 0.0022(6) 0.0005(6) C12 0.0197(7) 0.0216(8) 0.0225(7) -0.0018(6) -0.0012(6) -0.0014(6) C13 0.0318(9) 0.0258(8) 0.0243(8) 0.0025(7) 0.0045(7) -0.0019(7) C14 0.0365(9) 0.0235(8) 0.0289(8) 0.0019(7) 0.0012(7) 0.0020(7) C15 0.0270(8) 0.0307(9) 0.0257(8) -0.0032(7) -0.0011(6) 0.0038(7) C16 0.0314(9) 0.0346(10) 0.0244(8) 0.0028(7) 0.0075(7) 0.0000(7) C17 0.0304(9) 0.0253(8) 0.0277(8) 0.0064(7) 0.0022(7) -0.0006(7) C18 0.0482(12) 0.0433(12) 0.0366(10) -0.0046(9) 0.0063(9) 0.0177(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 S1 O5 1.4235(14) . ? S1 O6 1.4262(13) . ? S1 O4 1.5730(12) . ? S1 C12 1.7543(16) . ? O1 C1 1.2171(18) . ? O2 C5 1.2103(18) . ? O3 C9 1.4157(18) . ? O3 C10 1.4275(18) . ? O4 C11 1.4594(18) . ? N1 C1 1.3942(19) . ? N1 C5 1.4003(19) . ? N1 C8 1.4778(18) . ? C1 C2 1.490(2) . ? C2 C6 1.375(2) . ? C2 C3 1.416(2) . ? C3 C4 1.408(2) . ? C3 C3 1.410(3) 2_787 ? C4 C7 1.379(2) . ? C4 C5 1.480(2) . ? C6 C7 1.403(2) 2_787 ? C7 C6 1.403(2) 2_787 ? C8 C9 1.522(2) . ? C10 C11 1.496(2) . ? C12 C13 1.383(2) . ? C12 C17 1.383(2) . ? C13 C14 1.388(2) . ? C14 C15 1.388(2) . ? C15 C16 1.386(3) . ? C15 C18 1.504(2) . ? C16 C17 1.382(2) . ? 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 O5 S1 O6 120.58(9) . . ? O5 S1 O4 103.35(7) . . ? O6 S1 O4 108.72(7) . . ? O5 S1 C12 109.35(8) . . ? O6 S1 C12 108.21(8) . . ? O4 S1 C12 105.62(7) . . ? C9 O3 C10 112.76(12) . . ? C11 O4 S1 118.14(9) . . ? C1 N1 C5 125.05(12) . . ? C1 N1 C8 118.85(12) . . ? C5 N1 C8 116.06(12) . . ? O1 C1 N1 121.53(13) . . ? O1 C1 C2 121.80(13) . . ? N1 C1 C2 116.66(12) . . ? C6 C2 C3 120.03(13) . . ? C6 C2 C1 120.04(13) . . ? C3 C2 C1 119.93(13) . . ? C4 C3 C3 119.40(16) . 2_787 ? C4 C3 C2 121.10(13) . . ? C3 C3 C2 119.49(16) 2_787 . ? C7 C4 C3 120.18(13) . . ? C7 C4 C5 120.08(13) . . ? C3 C4 C5 119.73(13) . . ? O2 C5 N1 120.44(14) . . ? O2 C5 C4 122.20(14) . . ? N1 C5 C4 117.35(13) . . ? C2 C6 C7 120.41(13) . 2_787 ? C4 C7 C6 120.47(13) . 2_787 ? N1 C8 C9 110.60(12) . . ? O3 C9 C8 113.53(12) . . ? O3 C10 C11 108.77(12) . . ? O4 C11 C10 106.80(12) . . ? C13 C12 C17 120.74(15) . . ? C13 C12 S1 120.55(12) . . ? C17 C12 S1 118.70(13) . . ? C12 C13 C14 119.41(15) . . ? C15 C14 C13 120.97(16) . . ? C16 C15 C14 118.16(16) . . ? C16 C15 C18 120.55(16) . . ? C14 C15 C18 121.29(17) . . ? C17 C16 C15 121.87(16) . . ? C16 C17 C12 118.85(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.335 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.050