Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_d:\xray\recent\c4s1-3~1\sad _database_code_CSD 165414 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Atwood, J.L.' 'Barbour, Leonard J.' _publ_contact_author_name 'Prof J L Atwood' _publ_contact_author_address ; Chemistry Department University of Missouri-Columbia 125 Chemistry Building Columbia Missouri 65211 USA ; _publ_contact_author_email ATWOODJ@MISSOURI.EDU _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H40 N4 O16 S4' _chemical_formula_weight 1057.08 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 11.8339(9) _cell_length_b 11.8339(9) _cell_length_c 14.9028(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2087.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9110 _exptl_absorpt_correction_T_max 0.9250 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12722 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.11 _reflns_number_total 2302 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0723P)^2^+0.8113P] 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 0.06(10) _refine_ls_number_reflns 2302 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 S1 S 0.54881(5) 0.27002(6) 0.81094(5) 0.02219(18) Uani 1 1 d . . . O1 O 0.55289(17) 0.26307(16) 0.41492(12) 0.0252(4) Uani 1 1 d . . . C3 C 0.4494(2) 0.2635(2) 0.64463(17) 0.0197(5) Uani 1 1 d . . . H3 H 0.3807 0.2519 0.6764 0.024 Uiso 1 1 calc R . . C4 C 0.5491(2) 0.2814(2) 0.69192(17) 0.0201(5) Uani 1 1 d . . . C1 C 0.5522(2) 0.2779(2) 0.50648(17) 0.0192(5) Uani 1 1 d . . . O3 O 0.46974(19) 0.1822(2) 0.83414(14) 0.0354(5) Uani 1 1 d . . . N3A N 0.7939(2) 0.0436(2) 0.63167(18) 0.0310(6) Uani 1 1 d . . . H3A H 0.8671 0.0568 0.6323 0.037 Uiso 1 1 calc R . . C5 C 0.6485(2) 0.3049(2) 0.64680(17) 0.0197(5) Uani 1 1 d . . . H5 H 0.7156 0.3193 0.6798 0.024 Uiso 1 1 calc R . . O4 O 0.66285(17) 0.24456(17) 0.83494(13) 0.0295(5) Uani 1 1 d . . . O2 O 0.51452(19) 0.38024(18) 0.84718(14) 0.0331(5) Uani 1 1 d . . . C2 C 0.4491(2) 0.2624(2) 0.55094(16) 0.0181(5) Uani 1 1 d . . . C7 C 0.7575(2) 0.3420(2) 0.50344(17) 0.0197(5) Uani 1 1 d . . . H7A H 0.7809 0.2800 0.4628 0.024 Uiso 1 1 calc R . . H7B H 0.8193 0.3550 0.5470 0.024 Uiso 1 1 calc R . . C4A C 0.7409(3) 0.0232(3) 0.7079(2) 0.0311(7) Uani 1 1 d . . . H4A H 0.7824 0.0214 0.7625 0.037 Uiso 1 1 calc R . . C6 C 0.6509(2) 0.3077(2) 0.55329(17) 0.0190(5) Uani 1 1 d . . . C2A C 0.7386(3) 0.0446(3) 0.5536(2) 0.0333(7) Uani 1 1 d . . . H2A H 0.7790 0.0579 0.4996 0.040 Uiso 1 1 calc R . . C1A C 0.6238(3) 0.0268(3) 0.5504(2) 0.0314(7) Uani 1 1 d . . . H1A H 0.5857 0.0267 0.4943 0.038 Uiso 1 1 calc R . . C6A C 0.5631(2) 0.0089(2) 0.62971(18) 0.0277(6) Uani 1 1 d . . . C5A C 0.6254(3) 0.0042(3) 0.70912(19) 0.0288(6) Uani 1 1 d . . . H5A H 0.5884 -0.0120 0.7642 0.035 Uiso 1 1 calc R . . H1 H 0.6273 0.2360 0.3936 0.038(9) Uiso 1 1 d 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 0.0244(3) 0.0279(3) 0.0143(3) 0.0022(3) -0.0003(3) -0.0016(3) O1 0.0280(10) 0.0331(10) 0.0143(9) -0.0002(8) 0.0004(7) 0.0024(9) C3 0.0204(12) 0.0207(11) 0.0180(12) 0.0041(10) -0.0003(10) 0.0020(12) C4 0.0254(12) 0.0214(12) 0.0136(11) 0.0014(10) -0.0007(10) 0.0029(11) C1 0.0245(13) 0.0175(12) 0.0155(11) 0.0019(9) 0.0003(10) 0.0027(12) O3 0.0430(13) 0.0442(12) 0.0190(10) 0.0037(9) 0.0009(9) -0.0140(11) N3A 0.0345(14) 0.0287(12) 0.0299(14) 0.0009(11) -0.0010(10) 0.0054(11) C5 0.0205(12) 0.0207(12) 0.0181(12) 0.0018(9) -0.0016(10) -0.0010(10) O4 0.0338(11) 0.0356(12) 0.0192(9) 0.0063(8) 0.0027(8) 0.0032(9) O2 0.0375(12) 0.0364(12) 0.0253(10) -0.0042(9) 0.0028(9) 0.0013(9) C2 0.0193(11) 0.0179(11) 0.0171(12) 0.0004(9) -0.0027(9) -0.0002(11) C7 0.0195(13) 0.0196(12) 0.0201(12) 0.0030(10) 0.0015(10) 0.0010(10) C4A 0.0408(17) 0.0264(15) 0.0262(15) 0.0009(11) -0.0046(12) 0.0039(13) C6 0.0199(12) 0.0178(12) 0.0194(12) 0.0032(9) 0.0015(10) 0.0013(10) C2A 0.0389(17) 0.0373(16) 0.0236(14) -0.0005(13) 0.0026(12) 0.0059(14) C1A 0.0404(17) 0.0323(17) 0.0216(14) -0.0012(11) -0.0011(12) 0.0003(13) C6A 0.0370(16) 0.0224(13) 0.0236(14) -0.0028(11) 0.0022(12) 0.0014(12) C5A 0.0388(16) 0.0254(14) 0.0221(14) 0.0008(11) -0.0007(11) -0.0018(12) _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 O4 1.428(2) . ? S1 O3 1.440(2) . ? S1 O2 1.469(2) . ? S1 C4 1.779(3) . ? O1 C1 1.376(3) . ? C3 C4 1.391(4) . ? C3 C2 1.396(3) . ? C4 C5 1.383(4) . ? C1 C2 1.400(4) . ? C1 C6 1.406(4) . ? N3A C4A 1.320(4) . ? N3A C2A 1.335(4) . ? C5 C6 1.394(3) . ? C2 C7 1.523(3) 2_566 ? C7 C6 1.519(3) . ? C7 C2 1.523(3) 4_656 ? C4A C5A 1.386(4) . ? C2A C1A 1.376(5) . ? C1A C6A 1.399(4) . ? C6A C5A 1.395(4) . ? C6A C6A 1.507(6) 3_655 ? 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 O4 S1 O3 113.67(13) . . ? O4 S1 O2 110.87(13) . . ? O3 S1 O2 111.89(13) . . ? O4 S1 C4 105.31(12) . . ? O3 S1 C4 107.17(12) . . ? O2 S1 C4 107.45(12) . . ? C4 C3 C2 120.7(2) . . ? C5 C4 C3 120.4(2) . . ? C5 C4 S1 120.1(2) . . ? C3 C4 S1 119.5(2) . . ? O1 C1 C2 117.2(2) . . ? O1 C1 C6 121.3(2) . . ? C2 C1 C6 121.5(2) . . ? C4A N3A C2A 121.3(3) . . ? C4 C5 C6 120.6(2) . . ? C3 C2 C1 118.0(2) . . ? C3 C2 C7 122.4(2) . 2_566 ? C1 C2 C7 119.6(2) . 2_566 ? C6 C7 C2 110.7(2) . 4_656 ? N3A C4A C5A 120.6(3) . . ? C5 C6 C1 118.2(2) . . ? C5 C6 C7 120.8(2) . . ? C1 C6 C7 121.0(2) . . ? N3A C2A C1A 120.9(3) . . ? C2A C1A C6A 120.1(3) . . ? C5A C6A C1A 116.8(3) . . ? C5A C6A C6A 121.18(18) . 3_655 ? C1A C6A C6A 121.97(18) . 3_655 ? C4A C5A C6A 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.674 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.085