# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Institute of Life Sciences Medicinal Chemistry Department University of Hyderabad Campus 500046 India ; _publ_contact_author_email manojitpal@rediffmail.com _publ_contact_author_fax +91-40-66571581 _publ_contact_author_phone +91-40-66571500 #TrackingRef '2-MP.cif' _publ_contact_author_name 'Dr.Manojit Pal' _publ_author_name 'Manojit Pal' data_ils_drb_1_141_3_1 _database_code_depnum_ccdc_archive 'CCDC 818602' #TrackingRef '1-MP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 F6 N2 O4 S2' _chemical_formula_weight 500.45 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' F F 0.0171 0.0103 '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, z+1/2' _cell_length_a 9.917(5) _cell_length_b 14.232(7) _cell_length_c 14.838(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.095(11) _cell_angle_gamma 90.00 _cell_volume 2088.8(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(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 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11828 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.1023 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5898 _reflns_number_gt 3910 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+1.0217P] 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 0.67(16) _refine_ls_number_reflns 5898 _refine_ls_number_parameters 581 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.2720 _refine_ls_wR_factor_gt 0.2359 _refine_ls_goodness_of_fit_ref 1.357 _refine_ls_restrained_S_all 1.357 _refine_ls_shift/su_max 0.345 _refine_ls_shift/su_mean 0.014 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 S3 S 0.9019(2) 0.42198(15) 0.41602(17) 0.0417(5) Uani 1 1 d . . . S4 S 1.0512(3) 0.66606(16) 0.63770(19) 0.0484(6) Uani 1 1 d . . . S1 S 0.9790(3) 0.17400(18) 0.16516(19) 0.0522(7) Uani 1 1 d . . . S2 S 0.8883(3) 0.47000(16) 0.00420(19) 0.0493(6) Uani 1 1 d . . . C15 C 1.0927(10) 0.1567(6) -0.0885(7) 0.043(2) Uani 1 1 d . . . H15 H 1.0903 0.0915 -0.0845 0.052 Uiso 1 1 calc R . . C1 C 0.8856(9) 0.1574(6) -0.0131(6) 0.0371(19) Uani 1 1 d . . . C11 C 0.9974(9) 0.3084(6) -0.0586(6) 0.0363(19) Uani 1 1 d . . . C13 C 1.1994(10) 0.2982(7) -0.1367(7) 0.045(2) Uani 1 1 d . . . H13 H 1.2690 0.3274 -0.1648 0.054 Uiso 1 1 calc R . . C10 C 0.9945(10) 0.2091(6) -0.0516(7) 0.045(2) Uani 1 1 d . . . C8 C 0.7498(9) 0.0997(6) 0.0906(7) 0.043(2) Uani 1 1 d . . . C12 C 1.1016(11) 0.3508(6) -0.1007(8) 0.049(2) Uani 1 1 d . . . H12 H 1.1051 0.4159 -0.1046 0.058 Uiso 1 1 calc R . . C5 C 0.5179(11) -0.0082(7) 0.0772(9) 0.058(3) Uani 1 1 d . . . C3 C 0.6983(10) 0.0717(6) 0.0085(7) 0.043(2) Uani 1 1 d . . . C14 C 1.1945(10) 0.1992(6) -0.1313(7) 0.042(2) Uani 1 1 d . . . C6 C 0.5725(15) 0.0201(9) 0.1588(10) 0.071(4) Uani 1 1 d . . . H6 H 0.5306 -0.0006 0.2092 0.085 Uiso 1 1 calc R . . C7 C 0.6859(12) 0.0775(9) 0.1745(9) 0.061(3) Uani 1 1 d . . . H7 H 0.7173 0.0992 0.2313 0.074 Uiso 1 1 calc R . . C4 C 0.5837(12) 0.0158(7) -0.0027(9) 0.060(3) Uani 1 1 d . . . H4 H 0.5510 -0.0050 -0.0595 0.072 Uiso 1 1 calc R . . C16 C 1.3060(12) 0.1445(7) -0.1672(8) 0.054(3) Uani 1 1 d . . . C2 C 0.7820(11) 0.1095(7) -0.0547(8) 0.049(2) Uani 1 1 d . . . H2 H 0.7677 0.1024 -0.1169 0.059 Uiso 1 1 calc R . . C9 C 0.387(2) -0.0643(10) 0.0612(15) 0.101(6) Uani 1 1 d . . . F2 F 0.3641(14) -0.1047(9) 0.1434(10) 0.159(6) Uani 1 1 d . . . F3 F 0.2894(9) -0.0148(8) 0.0430(11) 0.130(4) Uani 1 1 d . . . F1 F 0.3969(13) -0.1324(8) 0.0065(11) 0.145(5) Uani 1 1 d . . . F6 F 1.4293(7) 0.1637(5) -0.1323(7) 0.084(2) Uani 1 1 d . . . F5 F 1.3123(12) 0.1566(7) -0.2560(6) 0.110(4) Uani 1 1 d . . . F4 F 1.2929(9) 0.0505(4) -0.1556(6) 0.080(2) Uani 1 1 d . . . N2 N 0.8892(7) 0.3613(5) -0.0297(6) 0.0418(19) Uani 1 1 d . . . H2A H 0.8130 0.3324 -0.0300 0.050 Uiso 1 1 calc R . . N1 N 0.8672(9) 0.1569(5) 0.0841(6) 0.0441(18) Uani 1 1 d . . . O2 O 1.0711(9) 0.2398(6) 0.1334(7) 0.075(3) Uani 1 1 d . . . O1 O 0.9121(9) 0.1925(7) 0.2437(6) 0.072(2) Uani 1 1 d . . . C17 C 1.0556(19) 0.0649(11) 0.1800(13) 0.099(5) Uani 1 1 d . . . H17A H 1.1381 0.0714 0.2174 0.148 Uiso 1 1 calc R . . H17B H 1.0752 0.0399 0.1222 0.148 Uiso 1 1 calc R . . H17C H 0.9958 0.0230 0.2084 0.148 Uiso 1 1 calc R . . O4 O 0.9677(11) 0.5246(6) -0.0517(8) 0.087(3) Uani 1 1 d . . . O3 O 0.7504(8) 0.4926(5) 0.0090(7) 0.069(2) Uani 1 1 d . . . C26 C 1.1266(8) 0.3117(6) 0.4531(6) 0.0340(18) Uani 1 1 d . . . C23 C 1.3450(11) 0.1986(7) 0.4373(8) 0.048(2) Uani 1 1 d . . . C19 C 1.0183(10) 0.3608(6) 0.5778(6) 0.039(2) Uani 1 1 d . . . C29 C 0.9423(10) 0.4963(7) 0.6682(7) 0.043(2) Uani 1 1 d . . . C33 C 0.8225(10) 0.3464(7) 0.6650(7) 0.045(2) Uani 1 1 d . . . H33 H 0.8118 0.2855 0.6430 0.054 Uiso 1 1 calc R . . C21 C 1.1945(10) 0.2731(6) 0.5303(6) 0.039(2) Uani 1 1 d . . . C24 C 1.2788(11) 0.2363(7) 0.3605(8) 0.054(3) Uani 1 1 d . . . H24 H 1.3096 0.2230 0.3041 0.065 Uiso 1 1 calc R . . C25 C 1.1689(11) 0.2929(7) 0.3665(7) 0.050(2) Uani 1 1 d . . . H25 H 1.1236 0.3183 0.3151 0.060 Uiso 1 1 calc R . . C28 C 0.9255(11) 0.4045(7) 0.6342(7) 0.047(2) Uani 1 1 d . . . C30 C 0.8491(10) 0.5258(7) 0.7307(8) 0.048(2) Uani 1 1 d . . . H30 H 0.8553 0.5869 0.7527 0.058 Uiso 1 1 calc R . . C31 C 0.7519(12) 0.4693(8) 0.7597(8) 0.055(3) Uani 1 1 d . . . H31 H 0.6946 0.4918 0.8017 0.066 Uiso 1 1 calc R . . C20 C 1.1249(11) 0.3058(8) 0.6024(7) 0.053(3) Uani 1 1 d . . . H20 H 1.1499 0.2908 0.6622 0.063 Uiso 1 1 calc R . . C32 C 0.7369(12) 0.3801(7) 0.7282(8) 0.055(3) Uani 1 1 d . . . C22 C 1.3021(12) 0.2153(7) 0.5195(8) 0.053(3) Uani 1 1 d . . . H22 H 1.3462 0.1871 0.5699 0.064 Uiso 1 1 calc R . . C27 C 1.4612(14) 0.1385(9) 0.4275(10) 0.072(4) Uani 1 1 d . . . F9 F 1.4866(11) 0.0759(6) 0.4905(7) 0.106(3) Uani 1 1 d . . . F8 F 1.4427(15) 0.0736(8) 0.3550(9) 0.141(5) Uani 1 1 d . . . F7 F 1.5649(11) 0.1790(6) 0.4004(13) 0.167(7) Uani 1 1 d . . . N3 N 1.0420(10) 0.5503(6) 0.6364(7) 0.057(2) Uani 1 1 d . . . H3 H 1.1070 0.5210 0.6132 0.069 Uiso 1 1 calc R . . C36 C 0.918(2) 0.7022(10) 0.5653(13) 0.096(5) Uani 1 1 d . . . H36A H 0.8770 0.7568 0.5896 0.144 Uiso 1 1 calc R . . H36B H 0.8523 0.6527 0.5582 0.144 Uiso 1 1 calc R . . H36C H 0.9503 0.7171 0.5075 0.144 Uiso 1 1 calc R . . O8 O 1.0264(10) 0.7010(6) 0.7225(6) 0.073(3) Uani 1 1 d . . . O7 O 1.1708(9) 0.6887(5) 0.5980(8) 0.081(3) Uani 1 1 d . . . C35 C 0.7743(13) 0.3368(9) 0.4021(9) 0.064(3) Uani 1 1 d . . . H35A H 0.7095 0.3556 0.3543 0.096 Uiso 1 1 calc R . . H35B H 0.7301 0.3305 0.4573 0.096 Uiso 1 1 calc R . . H35C H 0.8134 0.2776 0.3871 0.096 Uiso 1 1 calc R . . O5 O 0.9579(9) 0.4391(6) 0.3324(5) 0.063(2) Uani 1 1 d . . . O6 O 0.8535(9) 0.4994(5) 0.4654(6) 0.065(2) Uani 1 1 d . . . C34 C 0.6325(13) 0.3188(8) 0.7588(10) 0.067(4) Uani 1 1 d . . . F10 F 0.6604(13) 0.2303(7) 0.7577(13) 0.172(8) Uani 1 1 d . . . F12 F 0.5183(12) 0.3244(10) 0.7142(15) 0.208(10) Uani 1 1 d . . . F11 F 0.6000(17) 0.3362(11) 0.8412(9) 0.173(7) Uani 1 1 d . . . N4 N 1.0187(8) 0.3680(5) 0.4830(5) 0.0417(18) Uani 1 1 d . . . C18 C 0.961(2) 0.4687(13) 0.1049(15) 0.125(8) Uani 1 1 d . . . H18A H 1.0577 0.4667 0.1013 0.187 Uiso 1 1 calc R . . H18B H 0.9327 0.4143 0.1366 0.187 Uiso 1 1 calc R . . H18C H 0.9375 0.5244 0.1365 0.187 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 S3 0.0436(12) 0.0444(11) 0.0365(13) 0.0012(10) -0.0015(9) 0.0021(9) S4 0.0530(14) 0.0453(12) 0.0482(15) -0.0056(11) 0.0131(12) -0.0095(10) S1 0.0557(15) 0.0580(14) 0.0424(15) -0.0019(12) 0.0007(12) -0.0045(11) S2 0.0562(15) 0.0422(12) 0.0500(16) -0.0008(11) 0.0082(12) 0.0067(10) C15 0.048(5) 0.037(4) 0.046(6) -0.005(4) 0.010(4) 0.000(4) C1 0.032(4) 0.040(4) 0.038(5) 0.004(4) -0.002(4) 0.004(3) C11 0.033(4) 0.043(4) 0.034(5) 0.005(4) 0.010(4) 0.003(3) C13 0.041(5) 0.049(5) 0.045(6) 0.007(4) 0.005(4) -0.005(4) C10 0.049(5) 0.042(5) 0.046(6) -0.004(4) 0.015(4) -0.001(4) C8 0.030(4) 0.040(4) 0.060(7) 0.011(4) 0.016(4) 0.001(3) C12 0.060(6) 0.031(4) 0.056(7) 0.004(4) 0.014(5) -0.005(4) C5 0.053(6) 0.045(5) 0.077(9) 0.028(6) 0.015(6) 0.004(4) C3 0.046(5) 0.034(4) 0.049(6) 0.008(4) 0.001(4) 0.003(4) C14 0.039(5) 0.047(5) 0.040(5) -0.003(4) 0.004(4) -0.008(4) C6 0.083(9) 0.071(7) 0.062(9) 0.006(6) 0.030(7) -0.014(6) C7 0.054(7) 0.080(7) 0.054(7) 0.005(6) 0.025(5) -0.014(5) C4 0.064(7) 0.050(6) 0.068(8) 0.000(5) 0.012(6) -0.010(5) C16 0.057(7) 0.051(5) 0.055(7) -0.007(5) 0.019(5) -0.002(5) C2 0.046(5) 0.048(5) 0.052(6) 0.001(5) -0.010(5) -0.015(4) C9 0.105(13) 0.055(7) 0.145(17) 0.043(10) 0.032(12) -0.016(8) F2 0.160(12) 0.152(10) 0.172(13) 0.044(9) 0.057(10) -0.088(9) F3 0.054(6) 0.118(8) 0.220(15) 0.028(8) 0.021(7) -0.004(5) F1 0.116(9) 0.118(7) 0.204(14) -0.083(9) 0.043(9) -0.058(7) F6 0.041(4) 0.088(5) 0.124(8) -0.013(5) 0.013(4) 0.010(3) F5 0.141(9) 0.130(7) 0.066(5) 0.015(5) 0.053(6) 0.064(6) F4 0.096(6) 0.049(3) 0.099(6) -0.009(4) 0.035(5) 0.006(3) N2 0.034(4) 0.037(4) 0.057(5) 0.008(3) 0.020(4) 0.008(3) N1 0.046(5) 0.041(4) 0.046(5) 0.002(4) 0.004(4) 0.005(3) O2 0.049(5) 0.094(6) 0.080(6) 0.027(5) -0.010(4) -0.032(4) O1 0.067(6) 0.114(7) 0.037(4) -0.024(5) 0.009(4) -0.016(5) C17 0.088(11) 0.103(11) 0.103(13) 0.010(9) -0.002(9) 0.051(9) O4 0.091(7) 0.049(4) 0.128(9) 0.014(5) 0.052(7) 0.002(4) O3 0.055(5) 0.056(4) 0.098(7) 0.012(4) 0.025(5) 0.011(3) C26 0.025(4) 0.038(4) 0.039(5) -0.005(4) -0.001(3) -0.005(3) C23 0.049(6) 0.048(5) 0.051(6) 0.004(5) 0.020(5) 0.004(4) C19 0.043(5) 0.043(4) 0.032(5) -0.001(4) 0.012(4) 0.000(4) C29 0.047(5) 0.047(5) 0.033(5) -0.005(4) -0.001(4) 0.001(4) C33 0.039(5) 0.043(5) 0.054(6) 0.002(4) 0.015(4) -0.005(4) C21 0.051(5) 0.040(4) 0.028(5) 0.004(4) 0.008(4) 0.014(4) C24 0.055(6) 0.055(6) 0.054(7) -0.004(5) 0.024(5) -0.001(4) C25 0.054(6) 0.057(5) 0.040(6) 0.002(5) 0.013(5) -0.011(5) C28 0.064(6) 0.046(5) 0.036(5) 0.009(4) 0.029(5) 0.014(4) C30 0.044(5) 0.048(5) 0.054(6) -0.010(5) 0.014(5) 0.003(4) C31 0.060(7) 0.060(6) 0.046(6) -0.008(5) 0.009(5) -0.001(5) C20 0.049(6) 0.073(6) 0.036(6) 0.004(5) 0.004(4) 0.023(5) C32 0.062(7) 0.056(6) 0.048(7) 0.010(5) 0.012(5) 0.006(5) C22 0.060(7) 0.060(6) 0.040(6) 0.009(5) 0.008(5) 0.012(5) C27 0.071(8) 0.064(7) 0.085(10) 0.018(7) 0.036(7) 0.022(6) F9 0.120(8) 0.082(5) 0.122(8) 0.030(5) 0.049(6) 0.053(5) F8 0.165(11) 0.121(7) 0.142(10) -0.027(7) 0.037(8) 0.081(8) F7 0.074(6) 0.089(6) 0.35(2) 0.063(9) 0.105(10) 0.019(5) N3 0.067(6) 0.044(4) 0.065(6) -0.022(4) 0.033(5) -0.010(4) C36 0.132(15) 0.065(8) 0.088(12) 0.015(8) -0.006(10) 0.000(8) O8 0.100(7) 0.074(5) 0.049(5) -0.027(4) 0.022(5) -0.017(5) O7 0.069(6) 0.049(4) 0.132(9) -0.009(5) 0.049(6) -0.019(4) C35 0.051(7) 0.074(7) 0.065(8) -0.003(6) -0.012(6) 0.000(5) O5 0.068(5) 0.085(5) 0.035(4) 0.022(4) -0.001(4) -0.007(4) O6 0.074(5) 0.058(4) 0.061(5) -0.028(4) -0.011(4) 0.021(4) C34 0.064(8) 0.050(6) 0.092(10) 0.019(6) 0.034(7) 0.008(5) F10 0.118(9) 0.083(6) 0.33(2) 0.066(9) 0.133(12) 0.010(6) F12 0.067(7) 0.173(12) 0.38(3) 0.166(15) -0.032(11) -0.043(7) F11 0.201(14) 0.217(13) 0.114(9) -0.073(9) 0.106(10) -0.139(12) N4 0.055(5) 0.043(4) 0.028(4) 0.000(3) 0.009(3) 0.004(3) C18 0.125(16) 0.118(14) 0.124(17) -0.062(13) -0.045(13) 0.035(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 S3 O5 1.416(8) . ? S3 O6 1.425(7) . ? S3 N4 1.660(8) . ? S3 C35 1.754(12) . ? S4 O8 1.392(8) . ? S4 O7 1.398(8) . ? S4 N3 1.650(8) . ? S4 C36 1.721(19) . ? S1 O1 1.407(8) . ? S1 O2 1.412(8) . ? S1 N1 1.596(9) . ? S1 C17 1.736(13) . ? S2 O3 1.412(8) . ? S2 O4 1.416(9) . ? S2 C18 1.61(2) . ? S2 N2 1.627(8) . ? C15 C14 1.371(13) . ? C15 C10 1.372(13) . ? C1 C2 1.345(13) . ? C1 C10 1.457(13) . ? C1 N1 1.467(13) . ? C11 C12 1.384(13) . ? C11 N2 1.402(11) . ? C11 C10 1.418(12) . ? C13 C12 1.363(14) . ? C13 C14 1.411(13) . ? C8 C3 1.347(15) . ? C8 N1 1.430(12) . ? C8 C7 1.470(14) . ? C5 C6 1.35(2) . ? C5 C4 1.435(17) . ? C5 C9 1.53(2) . ? C3 C4 1.387(15) . ? C3 C2 1.403(15) . ? C14 C16 1.483(14) . ? C6 C7 1.396(18) . ? C16 F6 1.322(14) . ? C16 F5 1.335(14) . ? C16 F4 1.356(12) . ? C9 F3 1.209(19) . ? C9 F1 1.27(2) . ? C9 F2 1.38(2) . ? C26 C21 1.399(13) . ? C26 C25 1.406(13) . ? C26 N4 1.432(11) . ? C23 C22 1.342(14) . ? C23 C24 1.383(17) . ? C23 C27 1.450(15) . ? C19 C20 1.345(14) . ? C19 N4 1.411(12) . ? C19 C28 1.429(12) . ? C29 N3 1.363(13) . ? C29 C28 1.407(14) . ? C29 C30 1.419(13) . ? C33 C32 1.394(14) . ? C33 C28 1.415(13) . ? C21 C22 1.366(13) . ? C21 C20 1.394(13) . ? C24 C25 1.363(16) . ? C30 C31 1.348(15) . ? C31 C32 1.357(16) . ? C32 C34 1.451(15) . ? C27 F7 1.269(16) . ? C27 F9 1.303(15) . ? C27 F8 1.42(2) . ? C34 F12 1.272(19) . ? C34 F10 1.290(14) . ? C34 F11 1.309(17) . ? 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 S3 O6 119.0(6) . . ? O5 S3 N4 107.7(4) . . ? O6 S3 N4 107.2(4) . . ? O5 S3 C35 109.9(6) . . ? O6 S3 C35 109.2(6) . . ? N4 S3 C35 102.5(5) . . ? O8 S4 O7 120.6(6) . . ? O8 S4 N3 110.7(5) . . ? O7 S4 N3 105.8(5) . . ? O8 S4 C36 106.3(8) . . ? O7 S4 C36 107.7(9) . . ? N3 S4 C36 104.6(7) . . ? O1 S1 O2 120.5(6) . . ? O1 S1 N1 108.0(5) . . ? O2 S1 N1 106.3(5) . . ? O1 S1 C17 106.9(8) . . ? O2 S1 C17 110.4(8) . . ? N1 S1 C17 103.5(7) . . ? O3 S2 O4 119.1(6) . . ? O3 S2 C18 109.2(10) . . ? O4 S2 C18 108.5(11) . . ? O3 S2 N2 105.0(5) . . ? O4 S2 N2 109.0(5) . . ? C18 S2 N2 105.3(7) . . ? C14 C15 C10 120.8(8) . . ? C2 C1 C10 129.8(10) . . ? C2 C1 N1 107.7(9) . . ? C10 C1 N1 122.4(8) . . ? C12 C11 N2 121.1(8) . . ? C12 C11 C10 119.1(8) . . ? N2 C11 C10 119.5(8) . . ? C12 C13 C14 119.8(9) . . ? C15 C10 C11 119.6(8) . . ? C15 C10 C1 116.7(8) . . ? C11 C10 C1 123.5(8) . . ? C3 C8 N1 111.4(8) . . ? C3 C8 C7 122.9(9) . . ? N1 C8 C7 125.6(10) . . ? C13 C12 C11 120.8(8) . . ? C6 C5 C4 119.5(11) . . ? C6 C5 C9 125.2(12) . . ? C4 C5 C9 115.4(14) . . ? C8 C3 C4 122.2(10) . . ? C8 C3 C2 106.6(9) . . ? C4 C3 C2 131.1(11) . . ? C15 C14 C13 119.8(9) . . ? C15 C14 C16 121.8(8) . . ? C13 C14 C16 118.3(8) . . ? C5 C6 C7 126.2(11) . . ? C6 C7 C8 112.1(11) . . ? C3 C4 C5 117.0(12) . . ? F6 C16 F5 104.7(10) . . ? F6 C16 F4 104.4(9) . . ? F5 C16 F4 105.4(9) . . ? F6 C16 C14 116.2(9) . . ? F5 C16 C14 112.1(10) . . ? F4 C16 C14 113.1(8) . . ? C1 C2 C3 110.9(10) . . ? F3 C9 F1 114(2) . . ? F3 C9 F2 105.3(17) . . ? F1 C9 F2 105.7(13) . . ? F3 C9 C5 112.8(11) . . ? F1 C9 C5 112.9(14) . . ? F2 C9 C5 105.6(16) . . ? C11 N2 S2 128.8(6) . . ? C8 N1 C1 103.2(8) . . ? C8 N1 S1 124.1(7) . . ? C1 N1 S1 127.8(7) . . ? C21 C26 C25 121.1(8) . . ? C21 C26 N4 107.1(7) . . ? C25 C26 N4 131.8(9) . . ? C22 C23 C24 121.2(9) . . ? C22 C23 C27 120.1(11) . . ? C24 C23 C27 118.7(10) . . ? C20 C19 N4 104.7(8) . . ? C20 C19 C28 128.4(10) . . ? N4 C19 C28 126.9(9) . . ? N3 C29 C28 118.0(8) . . ? N3 C29 C30 125.6(9) . . ? C28 C29 C30 116.3(9) . . ? C32 C33 C28 120.3(9) . . ? C22 C21 C20 136.5(9) . . ? C22 C21 C26 118.3(8) . . ? C20 C21 C26 105.1(8) . . ? C25 C24 C23 120.7(10) . . ? C24 C25 C26 117.7(10) . . ? C29 C28 C33 119.7(8) . . ? C29 C28 C19 123.3(9) . . ? C33 C28 C19 116.4(9) . . ? C31 C30 C29 123.1(9) . . ? C30 C31 C32 120.8(10) . . ? C19 C20 C21 114.2(10) . . ? C31 C32 C33 119.7(10) . . ? C31 C32 C34 121.2(10) . . ? C33 C32 C34 119.1(10) . . ? C23 C22 C21 121.0(10) . . ? F7 C27 F9 114.7(14) . . ? F7 C27 F8 96.9(13) . . ? F9 C27 F8 96.2(11) . . ? F7 C27 C23 115.5(11) . . ? F9 C27 C23 116.5(10) . . ? F8 C27 C23 113.5(13) . . ? C29 N3 S4 126.9(7) . . ? F12 C34 F10 103.8(15) . . ? F12 C34 F11 101.8(14) . . ? F10 C34 F11 105.3(14) . . ? F12 C34 C32 115.3(12) . . ? F10 C34 C32 115.1(10) . . ? F11 C34 C32 114.0(12) . . ? C19 N4 C26 108.9(7) . . ? C19 N4 S3 125.3(6) . . ? C26 N4 S3 125.4(6) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.597 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.135 # Attachment '2-MP.cif' data_tri _database_code_depnum_ccdc_archive 'CCDC 818615' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H24 N2 O5 S2' _chemical_formula_sum 'C25 H24 N2 O5 S2' _chemical_formula_weight 496.58 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2712(4) _cell_length_b 12.0103(6) _cell_length_c 13.3107(6) _cell_angle_alpha 98.590(4) _cell_angle_beta 91.371(4) _cell_angle_gamma 108.406(4) _cell_volume 1237.00(10) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5109 _cell_measurement_theta_min 2.9220 _cell_measurement_theta_max 28.9329 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.254 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9417 _exptl_absorpt_correction_T_max 0.9702 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _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 8168 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 24.71 _reflns_number_total 4219 _reflns_number_gt 3536 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _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^)+(0.0451P)^2^+0.6516P] 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 4219 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 C1 C 0.7351(3) 0.69975(19) 0.10489(15) 0.0337(5) Uani 1 1 d . . . C2 C 0.6450(3) 0.6178(2) 0.15870(17) 0.0422(5) Uani 1 1 d . . . H2 H 0.5434 0.5574 0.1353 0.051 Uiso 1 1 calc R . . C3 C 0.7306(3) 0.6385(2) 0.25792(16) 0.0382(5) Uani 1 1 d . . . C4 C 0.8769(3) 0.73698(19) 0.26236(15) 0.0349(5) Uani 1 1 d . . . C5 C 0.6953(3) 0.5810(2) 0.34286(18) 0.0494(6) Uani 1 1 d . . . H5 H 0.6005 0.5131 0.3393 0.059 Uiso 1 1 calc R . . C6 C 0.7998(3) 0.6243(2) 0.43174(18) 0.0505(6) Uani 1 1 d . . . C7 C 0.9445(3) 0.7255(2) 0.43492(17) 0.0467(6) Uani 1 1 d . . . C8 C 0.9860(3) 0.7817(2) 0.35033(17) 0.0427(5) Uani 1 1 d . . . H8 H 1.0839 0.8472 0.3527 0.051 Uiso 1 1 calc R . . C9 C 1.0565(4) 0.7815(3) 0.53120(19) 0.0577(7) Uani 1 1 d . . . C10 C 1.2449(4) 0.8142(2) 0.52835(19) 0.0519(6) Uani 1 1 d . . . C11 C 1.3208(4) 0.7613(3) 0.4524(2) 0.0627(8) Uani 1 1 d . . . H11 H 1.2534 0.7065 0.3986 0.075 Uiso 1 1 calc R . . C12 C 1.4959(5) 0.7895(3) 0.4562(3) 0.0850(10) Uani 1 1 d . . . H12 H 1.5464 0.7533 0.4052 0.102 Uiso 1 1 calc R . . C13 C 1.5963(5) 0.8709(4) 0.5351(3) 0.0884(11) Uani 1 1 d . . . H13 H 1.7144 0.8891 0.5376 0.106 Uiso 1 1 calc R . . C14 C 1.5235(5) 0.9247(3) 0.6094(3) 0.0813(10) Uani 1 1 d . . . H14 H 1.5921 0.9806 0.6621 0.098 Uiso 1 1 calc R . . C15 C 1.3499(4) 0.8971(3) 0.6070(2) 0.0676(8) Uani 1 1 d . . . H15 H 1.3012 0.9340 0.6585 0.081 Uiso 1 1 calc R . . C16 C 0.7568(5) 0.5610(3) 0.5228(2) 0.0866(11) Uani 1 1 d . . . H16A H 0.7056 0.6048 0.5712 0.130 Uiso 1 1 calc R . . H16B H 0.8593 0.5559 0.5542 0.130 Uiso 1 1 calc R . . H16C H 0.6781 0.4824 0.5007 0.130 Uiso 1 1 calc R . . C17 C 0.9759(4) 1.0097(2) 0.1638(2) 0.0696(8) Uani 1 1 d . . . H17A H 1.0622 1.0786 0.1483 0.104 Uiso 1 1 calc R . . H17B H 0.9588 1.0212 0.2352 0.104 Uiso 1 1 calc R . . H17C H 0.8709 0.9981 0.1250 0.104 Uiso 1 1 calc R . . C18 C 0.6896(3) 0.71705(19) 0.00140(15) 0.0337(5) Uani 1 1 d . . . C19 C 0.5914(3) 0.7899(2) -0.01054(17) 0.0406(5) Uani 1 1 d . . . H19 H 0.5591 0.8288 0.0474 0.049 Uiso 1 1 calc R . . C20 C 0.5397(3) 0.8069(2) -0.10529(18) 0.0431(5) Uani 1 1 d . . . C21 C 0.5899(3) 0.7480(2) -0.18984(18) 0.0461(6) Uani 1 1 d . . . H21 H 0.5592 0.7590 -0.2544 0.055 Uiso 1 1 calc R . . C22 C 0.6847(3) 0.6731(2) -0.18092(17) 0.0451(6) Uani 1 1 d . . . H22 H 0.7158 0.6342 -0.2393 0.054 Uiso 1 1 calc R . . C23 C 0.7338(3) 0.65550(19) -0.08611(16) 0.0375(5) Uani 1 1 d . . . C24 C 0.4340(4) 0.8873(3) -0.1164(2) 0.0616(7) Uani 1 1 d . . . H24A H 0.3645 0.8881 -0.0597 0.092 Uiso 1 1 calc R . . H24B H 0.3620 0.8583 -0.1786 0.092 Uiso 1 1 calc R . . H24C H 0.5085 0.9666 -0.1178 0.092 Uiso 1 1 calc R . . C25 C 1.0829(5) 0.6124(4) -0.1919(4) 0.1156(16) Uani 1 1 d . . . H25A H 1.1331 0.5768 -0.2467 0.173 Uiso 1 1 calc R . . H25B H 1.1654 0.6451 -0.1343 0.173 Uiso 1 1 calc R . . H25C H 1.0478 0.6746 -0.2134 0.173 Uiso 1 1 calc R . . N1 N 0.8224(3) 0.57477(19) -0.07225(15) 0.0522(6) Uani 1 1 d . . . H1 H 0.8325 0.5613 -0.0111 0.063 Uiso 1 1 calc R . . N2 N 0.8831(2) 0.77513(16) 0.16678(13) 0.0353(4) Uani 1 1 d . . . O1 O 0.7886(3) 0.45805(18) -0.24525(14) 0.0751(6) Uani 1 1 d . . . O2 O 0.9633(3) 0.42587(18) -0.10737(14) 0.0667(6) Uani 1 1 d . . . O3 O 1.0435(2) 0.85885(17) 0.02552(12) 0.0571(5) Uani 1 1 d . . . O4 O 1.1888(2) 0.89898(18) 0.19603(14) 0.0651(5) Uani 1 1 d . . . O5 O 0.9918(3) 0.7992(3) 0.61136(15) 0.0968(9) Uani 1 1 d . . . S1 S 0.90660(9) 0.50519(6) -0.15782(5) 0.04905(19) Uani 1 1 d . . . S2 S 1.04116(7) 0.88500(5) 0.13269(4) 0.04104(17) 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 0.0341(11) 0.0376(12) 0.0285(11) 0.0031(9) -0.0008(9) 0.0116(9) C2 0.0378(13) 0.0476(14) 0.0337(12) 0.0060(10) -0.0016(10) 0.0035(10) C3 0.0384(12) 0.0454(13) 0.0300(11) 0.0070(9) 0.0029(9) 0.0121(10) C4 0.0388(12) 0.0408(12) 0.0255(11) 0.0053(9) 0.0008(9) 0.0136(10) C5 0.0491(15) 0.0568(15) 0.0381(14) 0.0160(11) 0.0077(11) 0.0074(12) C6 0.0543(16) 0.0675(17) 0.0326(13) 0.0189(12) 0.0069(11) 0.0185(13) C7 0.0500(15) 0.0644(16) 0.0275(12) 0.0073(11) -0.0004(10) 0.0214(13) C8 0.0428(13) 0.0484(14) 0.0310(12) 0.0052(10) -0.0035(10) 0.0076(11) C9 0.0658(18) 0.0775(19) 0.0293(13) 0.0071(12) -0.0046(12) 0.0238(15) C10 0.0635(17) 0.0569(16) 0.0368(13) 0.0105(11) -0.0120(12) 0.0213(13) C11 0.0690(19) 0.0583(17) 0.0617(18) 0.0011(14) -0.0112(15) 0.0268(15) C12 0.077(2) 0.090(3) 0.099(3) 0.009(2) -0.001(2) 0.047(2) C13 0.062(2) 0.103(3) 0.104(3) 0.031(2) -0.017(2) 0.027(2) C14 0.077(2) 0.086(2) 0.065(2) 0.0174(18) -0.0343(18) 0.0051(19) C15 0.078(2) 0.079(2) 0.0382(15) 0.0053(14) -0.0182(14) 0.0190(17) C16 0.089(2) 0.114(3) 0.0500(18) 0.0433(19) 0.0049(17) 0.011(2) C17 0.095(2) 0.0396(15) 0.070(2) 0.0075(13) 0.0049(17) 0.0159(15) C18 0.0335(11) 0.0364(11) 0.0280(11) 0.0032(9) -0.0032(9) 0.0080(9) C19 0.0418(13) 0.0461(13) 0.0349(12) 0.0022(10) -0.0002(10) 0.0178(11) C20 0.0442(13) 0.0459(13) 0.0407(13) 0.0083(10) -0.0053(10) 0.0165(11) C21 0.0577(15) 0.0515(14) 0.0310(12) 0.0079(10) -0.0091(11) 0.0208(12) C22 0.0602(16) 0.0512(14) 0.0270(12) 0.0014(10) -0.0034(10) 0.0250(12) C23 0.0429(13) 0.0378(12) 0.0314(12) 0.0026(9) -0.0044(9) 0.0146(10) C24 0.0694(19) 0.0698(19) 0.0583(17) 0.0121(14) -0.0044(14) 0.0403(16) C25 0.077(3) 0.112(3) 0.176(5) 0.053(3) 0.046(3) 0.039(2) N1 0.0799(16) 0.0637(14) 0.0268(10) 0.0012(9) -0.0047(10) 0.0462(12) N2 0.0374(10) 0.0389(10) 0.0262(9) 0.0066(7) -0.0030(7) 0.0073(8) O1 0.1202(18) 0.0732(13) 0.0397(10) -0.0145(9) -0.0226(11) 0.0549(13) O2 0.0973(15) 0.0712(13) 0.0472(11) -0.0052(9) -0.0112(10) 0.0571(12) O3 0.0561(11) 0.0697(12) 0.0344(9) 0.0095(8) 0.0093(8) 0.0039(9) O4 0.0423(10) 0.0818(14) 0.0579(12) 0.0258(10) -0.0130(9) -0.0042(9) O5 0.0827(16) 0.161(2) 0.0325(11) -0.0076(13) 0.0008(11) 0.0312(16) S1 0.0630(4) 0.0514(4) 0.0383(3) -0.0018(3) -0.0003(3) 0.0309(3) S2 0.0411(3) 0.0433(3) 0.0321(3) 0.0086(2) -0.0014(2) 0.0037(3) _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 C2 1.345(3) . ? C1 N2 1.423(3) . ? C1 C18 1.481(3) . ? C2 C3 1.433(3) . ? C3 C4 1.392(3) . ? C3 C5 1.401(3) . ? C4 C8 1.389(3) . ? C4 N2 1.412(3) . ? C5 C6 1.379(3) . ? C6 C7 1.405(4) . ? C6 C16 1.516(4) . ? C7 C8 1.393(3) . ? C7 C9 1.498(3) . ? C9 O5 1.225(3) . ? C9 C10 1.484(4) . ? C10 C11 1.382(4) . ? C10 C15 1.393(4) . ? C11 C12 1.378(4) . ? C12 C13 1.373(5) . ? C13 C14 1.356(5) . ? C14 C15 1.367(5) . ? C17 S2 1.744(3) . ? C18 C19 1.391(3) . ? C18 C23 1.404(3) . ? C19 C20 1.386(3) . ? C20 C21 1.382(3) . ? C20 C24 1.513(3) . ? C21 C22 1.382(3) . ? C22 C23 1.382(3) . ? C23 N1 1.417(3) . ? C25 S1 1.735(4) . ? N1 S1 1.6130(19) . ? N2 S2 1.6655(18) . ? O1 S1 1.424(2) . ? O2 S1 1.4270(19) . ? O3 S2 1.4161(17) . ? O4 S2 1.4174(18) . ? 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 C2 C1 N2 108.32(19) . . ? C2 C1 C18 127.8(2) . . ? N2 C1 C18 123.78(18) . . ? C1 C2 C3 109.1(2) . . ? C4 C3 C5 119.4(2) . . ? C4 C3 C2 107.33(19) . . ? C5 C3 C2 133.3(2) . . ? C8 C4 C3 121.4(2) . . ? C8 C4 N2 131.1(2) . . ? C3 C4 N2 107.55(18) . . ? C6 C5 C3 120.6(2) . . ? C5 C6 C7 118.9(2) . . ? C5 C6 C16 119.3(3) . . ? C7 C6 C16 121.8(3) . . ? C8 C7 C6 121.7(2) . . ? C8 C7 C9 116.9(2) . . ? C6 C7 C9 121.4(2) . . ? C4 C8 C7 118.1(2) . . ? O5 C9 C10 120.8(2) . . ? O5 C9 C7 119.7(3) . . ? C10 C9 C7 119.5(2) . . ? C11 C10 C15 118.3(3) . . ? C11 C10 C9 122.3(2) . . ? C15 C10 C9 119.3(3) . . ? C12 C11 C10 120.2(3) . . ? C13 C12 C11 120.2(3) . . ? C14 C13 C12 120.2(3) . . ? C13 C14 C15 120.2(3) . . ? C14 C15 C10 120.8(3) . . ? C19 C18 C23 118.6(2) . . ? C19 C18 C1 119.70(19) . . ? C23 C18 C1 121.55(19) . . ? C20 C19 C18 122.7(2) . . ? C21 C20 C19 117.2(2) . . ? C21 C20 C24 121.1(2) . . ? C19 C20 C24 121.7(2) . . ? C22 C21 C20 121.7(2) . . ? C21 C22 C23 120.6(2) . . ? C22 C23 C18 119.1(2) . . ? C22 C23 N1 123.2(2) . . ? C18 C23 N1 117.65(19) . . ? C23 N1 S1 127.54(16) . . ? C4 N2 C1 107.67(17) . . ? C4 N2 S2 125.37(15) . . ? C1 N2 S2 126.91(14) . . ? O1 S1 O2 119.15(12) . . ? O1 S1 N1 108.71(12) . . ? O2 S1 N1 105.48(11) . . ? O1 S1 C25 107.7(2) . . ? O2 S1 C25 109.13(18) . . ? N1 S1 C25 105.90(18) . . ? O3 S2 O4 119.70(12) . . ? O3 S2 N2 106.87(10) . . ? O4 S2 N2 106.97(10) . . ? O3 S2 C17 109.26(14) . . ? O4 S2 C17 109.07(15) . . ? N2 S2 C17 103.77(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.042