# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/460 data_jmk _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O4 S2' _chemical_formula_weight 340.41 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.389(2) _cell_length_b 10.165(2) _cell_length_c 12.128(3) _cell_angle_alpha 109.600(10) _cell_angle_beta 107.55(2) _cell_angle_gamma 94.24(2) _cell_volume 802.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 1890 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1767 _reflns_number_gt 1682 _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 w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+0.0741P] 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_number_reflns 1767 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.33479(16) 0.35857(14) 0.35401(12) 0.0418(4) Uani 1 d . . . S2 S 0.36262(17) 0.47471(16) 0.24932(13) 0.0489(4) Uani 1 d . . . N1 N 0.1335(6) 0.4666(5) 0.1802(4) 0.0477(11) Uani 1 d . . . N2 N -0.1836(5) 0.3759(5) 0.1453(4) 0.0468(11) Uani 1 d . . . O1 O 0.2538(5) 0.2099(4) 0.4694(4) 0.0584(11) Uani 1 d . . . O2 O -0.0050(4) 0.1765(4) 0.5163(3) 0.0477(9) Uani 1 d . . . O3 O -0.2555(4) 0.2976(3) 0.4674(3) 0.0416(8) Uani 1 d . . . O4 O -0.2484(4) 0.4441(4) 0.3706(3) 0.0422(8) Uani 1 d . . . C1 C -0.1780(6) 0.3515(5) 0.3987(4) 0.0328(10) Uani 1 d . . . C2 C -0.2119(6) 0.1667(5) 0.4793(5) 0.0422(12) Uani 1 d . . . C3 C -0.2669(7) 0.1560(6) 0.5836(5) 0.0526(14) Uani 1 d . . . H3A H -0.2402 0.0691 0.5940 0.079 Uiso 1 calc R . . H3B H -0.4025 0.1565 0.5658 0.079 Uiso 1 calc R . . H3C H -0.1937 0.2356 0.6588 0.079 Uiso 1 calc R . . C4 C -0.3130(8) 0.0416(6) 0.3590(6) 0.0585(15) Uani 1 d . . . H4A H -0.2820 -0.0444 0.3698 0.088 Uiso 1 calc R . . H4B H -0.2712 0.0530 0.2945 0.088 Uiso 1 calc R . . H4C H -0.4503 0.0364 0.3359 0.088 Uiso 1 calc R . . C5 C 0.0887(7) 0.2273(5) 0.4558(5) 0.0417(12) Uani 1 d . . . C6 C -0.0108(6) 0.2992(5) 0.3773(4) 0.0347(11) Uani 1 d . . . C7 C 0.0890(6) 0.3470(5) 0.3121(4) 0.0347(11) Uani 1 d . . . C8 C 0.0124(6) 0.3984(5) 0.2107(4) 0.0365(11) Uani 1 d . . . C9 C -0.3015(7) 0.2347(6) 0.0991(5) 0.0545(15) Uani 1 d . . . H9A H -0.4354 0.2430 0.0868 0.065 Uiso 1 calc R . . H9B H -0.2601 0.1926 0.1612 0.065 Uiso 1 calc R . . C10 C -0.2881(11) 0.1386(8) -0.0208(8) 0.091(2) Uani 1 d . . . H10 H -0.3202 0.1730 -0.0848 0.109 Uiso 1 calc R . . C11 C -0.2411(14) 0.0200(12) -0.0492(12) 0.158(5) Uani 1 d . . . H11A H -0.2070 -0.0218 0.0097 0.189 Uiso 1 calc R . . H11B H -0.2401 -0.0268 -0.1293 0.189 Uiso 1 calc R . . C12 C -0.2441(8) 0.4641(6) 0.0715(5) 0.0550(15) Uani 1 d . . . H12A H -0.3792 0.4283 0.0191 0.066 Uiso 1 calc R . . H12B H -0.1687 0.4568 0.0174 0.066 Uiso 1 calc R . . C13 C -0.2181(8) 0.6169(7) 0.1527(6) 0.0607(16) Uani 1 d . . . H13 H -0.2422 0.6366 0.2270 0.073 Uiso 1 calc R . . C14 C -0.1653(11) 0.7221(8) 0.1271(7) 0.084(2) Uani 1 d . . . H14A H -0.1400 0.7063 0.0536 0.100 Uiso 1 calc R . . H14B H -0.1520 0.8147 0.1821 0.100 Uiso 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 0.0235(6) 0.0540(8) 0.0537(8) 0.0264(7) 0.0126(5) 0.0151(5) S2 0.0300(7) 0.0686(10) 0.0617(9) 0.0356(8) 0.0204(6) 0.0158(6) N1 0.034(2) 0.067(3) 0.052(3) 0.032(2) 0.017(2) 0.016(2) N2 0.027(2) 0.060(3) 0.051(3) 0.029(2) 0.0020(19) 0.0081(19) O1 0.0310(18) 0.074(3) 0.092(3) 0.054(2) 0.0214(19) 0.0295(18) O2 0.0293(17) 0.059(2) 0.066(2) 0.040(2) 0.0118(16) 0.0168(16) O3 0.0315(17) 0.0436(19) 0.060(2) 0.0288(18) 0.0173(16) 0.0171(15) O4 0.0351(17) 0.046(2) 0.058(2) 0.0290(18) 0.0193(16) 0.0230(16) C1 0.025(2) 0.035(3) 0.033(3) 0.013(2) 0.0039(19) 0.005(2) C2 0.027(2) 0.042(3) 0.062(3) 0.028(3) 0.010(2) 0.011(2) C3 0.044(3) 0.058(4) 0.069(4) 0.036(3) 0.024(3) 0.013(3) C4 0.055(3) 0.050(3) 0.066(4) 0.025(3) 0.012(3) 0.004(3) C5 0.033(3) 0.046(3) 0.055(3) 0.029(3) 0.015(2) 0.017(2) C6 0.023(2) 0.038(3) 0.044(3) 0.018(2) 0.009(2) 0.0123(19) C7 0.024(2) 0.035(3) 0.043(3) 0.014(2) 0.008(2) 0.0106(19) C8 0.029(2) 0.044(3) 0.038(3) 0.017(2) 0.011(2) 0.013(2) C9 0.036(3) 0.057(4) 0.056(4) 0.017(3) 0.002(3) 0.001(3) C10 0.087(5) 0.067(5) 0.084(5) 0.012(4) 0.004(4) 0.008(4) C11 0.105(8) 0.123(9) 0.173(11) -0.010(8) 0.020(7) 0.039(7) C12 0.039(3) 0.072(4) 0.049(3) 0.029(3) 0.002(2) 0.014(3) C13 0.047(3) 0.074(4) 0.065(4) 0.034(4) 0.014(3) 0.023(3) C14 0.098(6) 0.078(5) 0.078(5) 0.030(4) 0.029(4) 0.033(4) _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 C7 1.715(4) . ? S1 S2 2.0433(19) . ? S2 N1 1.629(4) . ? N1 C8 1.303(6) . ? N2 C8 1.384(5) . ? N2 C9 1.454(7) . ? N2 C12 1.471(6) . ? O1 C5 1.215(5) . ? O2 C5 1.339(6) . ? O2 C2 1.443(5) . ? O3 C1 1.368(6) . ? O3 C2 1.434(6) . ? O4 C1 1.206(5) . ? C1 C6 1.441(6) . ? C2 C3 1.473(7) . ? C2 C4 1.503(8) . ? C5 C6 1.451(6) . ? C6 C7 1.400(6) . ? C7 C8 1.469(6) . ? C9 C10 1.491(9) . ? C10 C11 1.244(11) . ? C12 C13 1.495(8) . ? C13 C14 1.275(9) . ? 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 C7 S1 S2 93.57(17) . . ? N1 S2 S1 98.10(17) . . ? C8 N1 S2 116.5(4) . . ? C8 N2 C9 119.4(4) . . ? C8 N2 C12 116.6(4) . . ? C9 N2 C12 116.6(4) . . ? C5 O2 C2 118.0(4) . . ? C1 O3 C2 119.4(4) . . ? O4 C1 O3 116.6(4) . . ? O4 C1 C6 127.3(4) . . ? O3 C1 C6 115.9(4) . . ? O3 C2 O2 108.5(4) . . ? O3 C2 C3 107.1(4) . . ? O2 C2 C3 106.5(4) . . ? O3 C2 C4 111.3(4) . . ? O2 C2 C4 110.5(4) . . ? C3 C2 C4 112.7(4) . . ? O1 C5 O2 117.7(4) . . ? O1 C5 C6 123.4(5) . . ? O2 C5 C6 118.9(4) . . ? C7 C6 C1 122.9(4) . . ? C7 C6 C5 117.5(4) . . ? C1 C6 C5 117.1(4) . . ? C6 C7 C8 128.4(4) . . ? C6 C7 S1 119.7(3) . . ? C8 C7 S1 111.8(3) . . ? N1 C8 N2 118.6(4) . . ? N1 C8 C7 118.9(4) . . ? N2 C8 C7 122.5(4) . . ? N2 C9 C10 112.5(5) . . ? C11 C10 C9 130.6(10) . . ? N2 C12 C13 111.8(5) . . ? C14 C13 C12 124.5(7) . . ? _diffrn_measured_fraction_theta_max 0.626 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.626 _refine_diff_density_max 0.434 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.083 data_j _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N2 O3 S2' _chemical_formula_weight 258.31 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.517(2) _cell_length_b 19.328(2) _cell_length_c 7.9740(10) _cell_angle_alpha 90.000(10) _cell_angle_beta 107.39(2) _cell_angle_gamma 90.000(10) _cell_volume 1105.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.474 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 1506 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1388 _reflns_number_gt 1342 _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 w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.1820P] 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_number_reflns 1388 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.003 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.73437(12) 0.01025(4) 0.81149(10) 0.0365(2) Uani 1 d . . . S2 S 0.82237(13) 0.11302(5) 0.79389(12) 0.0489(3) Uani 1 d . . . N1 N 0.8509(4) 0.13754(14) 0.9996(4) 0.0441(7) Uani 1 d . . . N2 N 0.6903(3) -0.14230(12) 1.2359(3) 0.0336(6) Uani 1 d . . . O1 O 0.7596(4) 0.01955(13) 1.4575(3) 0.0565(7) Uani 1 d . . . O2 O 0.8242(3) 0.09246(11) 1.2648(3) 0.0413(6) Uani 1 d . . . O3 O 0.6099(3) -0.10412(11) 0.9561(3) 0.0425(6) Uani 1 d . . . C1 C 0.7702(4) 0.02605(15) 1.3125(4) 0.0368(8) Uani 1 d . . . C2 C 0.7373(4) -0.01988(15) 1.1600(4) 0.0290(6) Uani 1 d . . . C3 C 0.7589(4) 0.02070(15) 1.0276(4) 0.0285(7) Uani 1 d . . . C4 C 0.8144(4) 0.08870(16) 1.0933(4) 0.0340(7) Uani 1 d . . . C5 C 0.6750(4) -0.09222(15) 1.1150(4) 0.0301(7) Uani 1 d . . . C6 C 0.6333(5) -0.21217(16) 1.1680(4) 0.0431(8) Uani 1 d . . . H6A H 0.5204 -0.2090 1.0697 0.052 Uiso 1 calc R . . H6B H 0.6053 -0.2394 1.2591 0.052 Uiso 1 calc R . . C7 C 0.7820(6) -0.24848(18) 1.1089(5) 0.0594(11) Uani 1 d . . . H7A H 0.7385 -0.2936 1.0651 0.089 Uiso 1 calc R . . H7B H 0.8930 -0.2529 1.2066 0.089 Uiso 1 calc R . . H7C H 0.8089 -0.2220 1.0176 0.089 Uiso 1 calc R . . C8 C 0.7995(5) -0.13771(17) 1.4217(4) 0.0426(8) Uani 1 d . . . H8A H 0.8591 -0.0927 1.4435 0.051 Uiso 1 calc R . . H8B H 0.8969 -0.1725 1.4465 0.051 Uiso 1 calc R . . C9 C 0.6839(6) -0.1478(2) 1.5447(5) 0.0667(12) Uani 1 d . . . H9A H 0.7626 -0.1448 1.6640 0.100 Uiso 1 calc R . . H9B H 0.6256 -0.1925 1.5249 0.100 Uiso 1 calc R . . H9C H 0.5898 -0.1125 1.5237 0.100 Uiso 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 0.0431(5) 0.0417(4) 0.0272(4) 0.0017(3) 0.0142(3) 0.0015(4) S2 0.0556(6) 0.0480(5) 0.0493(5) 0.0154(4) 0.0251(4) -0.0014(4) N1 0.0449(17) 0.0351(15) 0.0528(18) 0.0039(13) 0.0153(14) -0.0038(13) N2 0.0360(15) 0.0314(13) 0.0332(14) 0.0010(11) 0.0102(12) -0.0035(11) O1 0.088(2) 0.0553(16) 0.0299(13) -0.0063(11) 0.0227(13) -0.0019(14) O2 0.0561(15) 0.0322(12) 0.0337(12) -0.0063(9) 0.0105(11) -0.0063(10) O3 0.0579(15) 0.0349(12) 0.0294(12) -0.0052(9) 0.0051(11) -0.0003(11) C1 0.047(2) 0.0333(17) 0.0291(16) -0.0010(13) 0.0094(15) -0.0004(14) C2 0.0295(17) 0.0302(15) 0.0275(15) 0.0006(12) 0.0089(13) 0.0014(13) C3 0.0255(15) 0.0326(16) 0.0277(16) -0.0022(12) 0.0085(12) 0.0054(12) C4 0.0344(17) 0.0320(16) 0.0361(17) 0.0003(13) 0.0113(14) 0.0004(14) C5 0.0308(17) 0.0305(15) 0.0298(16) -0.0024(12) 0.0104(13) 0.0018(13) C6 0.050(2) 0.0307(17) 0.050(2) -0.0019(15) 0.0161(17) -0.0097(15) C7 0.069(3) 0.0350(19) 0.079(3) -0.0073(19) 0.030(2) -0.0008(18) C8 0.046(2) 0.0399(18) 0.0381(19) 0.0061(14) 0.0066(16) -0.0008(16) C9 0.088(3) 0.076(3) 0.040(2) -0.0014(19) 0.027(2) -0.022(2) _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 C3 1.690(3) . ? S1 S2 2.1114(13) . ? S2 N1 1.658(3) . ? N1 C4 1.283(4) . ? N2 C5 1.347(4) . ? N2 C8 1.466(4) . ? N2 C6 1.470(4) . ? O1 C1 1.189(4) . ? O2 C4 1.350(4) . ? O2 C1 1.431(4) . ? O3 C5 1.235(3) . ? C1 C2 1.465(4) . ? C2 C3 1.363(4) . ? C2 C5 1.484(4) . ? C3 C4 1.430(4) . ? C6 C7 1.509(5) . ? C8 C9 1.505(5) . ? 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 C3 S1 S2 90.83(11) . . ? N1 S2 S1 98.83(10) . . ? C4 N1 S2 112.3(2) . . ? C5 N2 C8 125.6(3) . . ? C5 N2 C6 116.3(2) . . ? C8 N2 C6 116.2(2) . . ? C4 O2 C1 106.7(2) . . ? O1 C1 O2 117.4(3) . . ? O1 C1 C2 134.3(3) . . ? O2 C1 C2 108.3(2) . . ? C3 C2 C1 105.3(3) . . ? C3 C2 C5 117.2(3) . . ? C1 C2 C5 137.3(3) . . ? C2 C3 C4 109.5(3) . . ? C2 C3 S1 136.0(2) . . ? C4 C3 S1 114.5(2) . . ? N1 C4 O2 126.4(3) . . ? N1 C4 C3 123.5(3) . . ? O2 C4 C3 110.0(3) . . ? O3 C5 N2 121.5(3) . . ? O3 C5 C2 115.0(3) . . ? N2 C5 C2 123.4(3) . . ? N2 C6 C7 112.3(3) . . ? N2 C8 C9 113.1(3) . . ? _diffrn_measured_fraction_theta_max 0.691 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.691 _refine_diff_density_max 0.261 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.074