# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Francisco M. Romero' 'Eugenio Coronado' 'Carlos Gimenez-Saiz' 'Mael Nicolas' 'Eduard Rusanov' 'Helen Stoeckli-Evans' _publ_contact_author_name 'Dr Francisco M. Romero' _publ_contact_author_address ; Institut de Ciencia Molecular Universitat de Valencia Dr. Moliner, 50 Burjassot 46100 SPAIN ; _publ_contact_author_email FMRM@UV.ES _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis, crystal structures and electronic properties of imidazoline nitroxide radicals bearing active groups in electropolymerisation ; _publ_section_exptl_refinement ; There are three independent molecules per asymmetric unit. Molecule 1 (S1) is normal; Molecules 2 (S2) and 3 (S3) show two alternate positions for the heterocyclic ring. The S and C atoms involved were split and the occupancies refined S2a/S2b (= C24a/C24b) = 0.677/0.323; S3a/S3b (= C44a/C44b) = 0.727/0.273. The bond distances involved were also constrained, with C-S 1.71(2)\%A and C-C 1.43 (2)\%A. The imino nitroxide group in Molecule 3 is also disordered with two alternative positions for atom O31; refined occupancies O31a/O31b = 0.427/0.573. ; data_compound5 _database_code_CSD 199926 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H19 N2 O S' _chemical_formula_sum 'C17 H19 N2 O S' _chemical_formula_weight 299.40 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 9.3399(9) _cell_length_b 11.1211(12) _cell_length_c 23.606(2) _cell_angle_alpha 89.342(12) _cell_angle_beta 85.858(11) _cell_angle_gamma 75.866(12) _cell_volume 2371.5(4) _cell_formula_units_Z 6 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6494 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 25.92 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 954 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18613 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.1290 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.92 _reflns_number_total 8598 _reflns_number_gt 3701 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; ? ; _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^)+(0.0609P)^2^] 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 8598 _refine_ls_number_parameters 632 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 0.789 _refine_ls_restrained_S_all 0.793 _refine_ls_shift/su_max 0.047 _refine_ls_shift/su_mean 0.002 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 0.40820(13) 1.00872(11) 0.43699(5) 0.0628(3) Uani 1 1 d . . . O1 O 0.0378(3) 0.6313(3) 0.15270(13) 0.0722(9) Uani 1 1 d . . . N1 N 0.1266(3) 0.6743(3) 0.11850(13) 0.0477(8) Uani 1 1 d . . . N2 N 0.2818(3) 0.7877(3) 0.08938(13) 0.0449(8) Uani 1 1 d . . . C1 C 0.3747(4) 0.9944(3) 0.36740(15) 0.0421(9) Uani 1 1 d . . . H1A H 0.3835 1.0545 0.3393 0.050 Uiso 1 1 calc R . . C2 C 0.3341(3) 0.8875(3) 0.35664(14) 0.0299(8) Uani 1 1 d . . . C3 C 0.3308(4) 0.8170(3) 0.40684(16) 0.0443(9) Uani 1 1 d . . . H3A H 0.3056 0.7392 0.4080 0.053 Uiso 1 1 calc R . . C4 C 0.3688(4) 0.8737(3) 0.45511(15) 0.0444(9) Uani 1 1 d . . . H4A H 0.3715 0.8401 0.4923 0.053 Uiso 1 1 calc R . . C5 C 0.2986(3) 0.8518(3) 0.29997(14) 0.0285(7) Uani 1 1 d . . . C6 C 0.2194(3) 0.7627(3) 0.29354(14) 0.0335(8) Uani 1 1 d . . . H6A H 0.1869 0.7237 0.3264 0.040 Uiso 1 1 calc R . . C7 C 0.1864(3) 0.7290(3) 0.24055(14) 0.0322(8) Uani 1 1 d . . . H7A H 0.1318 0.6679 0.2374 0.039 Uiso 1 1 calc R . . C8 C 0.2332(3) 0.7848(3) 0.19218(14) 0.0280(7) Uani 1 1 d . . . C9 C 0.3118(4) 0.8747(3) 0.19815(15) 0.0353(8) Uani 1 1 d . . . H9A H 0.3440 0.9137 0.1653 0.042 Uiso 1 1 calc R . . C10 C 0.3438(4) 0.9080(3) 0.25095(15) 0.0360(8) Uani 1 1 d . . . H10A H 0.3972 0.9699 0.2540 0.043 Uiso 1 1 calc R . . C11 C 0.2129(3) 0.7499(3) 0.13319(14) 0.0281(7) Uani 1 1 d . . . C12 C 0.1519(3) 0.6408(3) 0.05773(14) 0.0342(8) Uani 1 1 d . . . C13 C 0.0030(4) 0.6456(4) 0.03374(19) 0.0604(12) Uani 1 1 d . . . H13C H 0.0187 0.6237 -0.0067 0.091 Uiso 1 1 calc R . . H13B H -0.0609 0.7295 0.0384 0.091 Uiso 1 1 calc R . . H13A H -0.0444 0.5866 0.0541 0.091 Uiso 1 1 calc R . . C14 C 0.2498(4) 0.5107(3) 0.05234(17) 0.0499(10) Uani 1 1 d . . . H14C H 0.2683 0.4869 0.0121 0.075 Uiso 1 1 calc R . . H14B H 0.2005 0.4530 0.0727 0.075 Uiso 1 1 calc R . . H14A H 0.3441 0.5080 0.0686 0.075 Uiso 1 1 calc R . . C15 C 0.2269(3) 0.7446(3) 0.03691(14) 0.0334(8) Uani 1 1 d . . . C16 C 0.1227(4) 0.8614(4) 0.01444(18) 0.0594(11) Uani 1 1 d . . . H16C H 0.0815 0.8406 -0.0201 0.089 Uiso 1 1 calc R . . H16B H 0.1781 0.9245 0.0058 0.089 Uiso 1 1 calc R . . H16A H 0.0421 0.8936 0.0433 0.089 Uiso 1 1 calc R . . C17 C 0.3590(4) 0.7044(4) -0.00576(18) 0.0587(11) Uani 1 1 d . . . H17C H 0.3268 0.6759 -0.0407 0.088 Uiso 1 1 calc R . . H17B H 0.4328 0.6368 0.0102 0.088 Uiso 1 1 calc R . . H17A H 0.4029 0.7747 -0.0143 0.088 Uiso 1 1 calc R . . S2A S -0.2132(2) 0.6915(3) 0.42696(15) 0.0571(9) Uani 0.677(6) 1 d PD . . C24B C -0.199(2) 0.670(3) 0.4216(13) 0.12(2) Uani 0.323(6) 1 d PD . . S2B S -0.1416(10) 0.7399(9) 0.4787(4) 0.068(3) Uani 0.323(6) 1 d PD . . C24A C -0.1257(16) 0.7369(17) 0.4848(8) 0.074(7) Uani 0.677(6) 1 d PD . . O2 O 0.6002(3) 0.1856(3) 0.27676(12) 0.0720(9) Uani 1 1 d . . . N21 N 0.6748(3) 0.1811(3) 0.31990(13) 0.0398(7) Uani 1 1 d . . . N22 N 0.7327(3) 0.2238(2) 0.40615(12) 0.0377(7) Uani 1 1 d . . . C21 C -0.0660(4) 0.5878(4) 0.39792(19) 0.0484(10) Uani 1 1 d D . . H21 H -0.067(4) 0.539(4) 0.364(2) 0.078(14) Uiso 1 1 d . . . C22 C 0.0594(4) 0.5797(3) 0.42751(15) 0.0353(8) Uani 1 1 d . . . C23 C 0.0273(5) 0.6609(4) 0.47390(19) 0.0477(10) Uani 1 1 d D . . H23 H 0.087(4) 0.668(3) 0.4989(17) 0.051(12) Uiso 1 1 d . . . C25 C 0.2051(3) 0.4956(3) 0.41176(14) 0.0304(8) Uani 1 1 d . . . C26 C 0.2327(3) 0.4279(3) 0.36114(15) 0.0397(9) Uani 1 1 d . . . H26A H 0.1563 0.4377 0.3357 0.048 Uiso 1 1 calc R . . C27 C 0.3673(3) 0.3470(3) 0.34683(15) 0.0382(9) Uani 1 1 d . . . H27A H 0.3821 0.3022 0.3120 0.046 Uiso 1 1 calc R . . C28 C 0.4819(3) 0.3305(3) 0.38294(14) 0.0296(7) Uani 1 1 d . . . C29 C 0.4553(4) 0.3969(3) 0.43330(16) 0.0443(9) Uani 1 1 d . . . H29A H 0.5319 0.3869 0.4586 0.053 Uiso 1 1 calc R . . C30 C 0.3200(4) 0.4773(3) 0.44782(16) 0.0447(9) Uani 1 1 d . . . H30A H 0.3050 0.5209 0.4830 0.054 Uiso 1 1 calc R . . C31 C 0.6293(3) 0.2456(3) 0.37076(15) 0.0315(8) Uani 1 1 d . . . C32 C 0.8710(3) 0.1432(3) 0.37814(15) 0.0362(8) Uani 1 1 d . . . C33 C 0.9741(4) 0.2296(4) 0.36462(18) 0.0552(11) Uani 1 1 d . . . H33C H 1.0675 0.1822 0.3459 0.083 Uiso 1 1 calc R . . H33B H 0.9938 0.2661 0.4000 0.083 Uiso 1 1 calc R . . H33A H 0.9268 0.2958 0.3394 0.083 Uiso 1 1 calc R . . C34 C 0.9402(4) 0.0457(4) 0.42047(17) 0.0564(11) Uani 1 1 d . . . H34C H 1.0314 -0.0077 0.4027 0.085 Uiso 1 1 calc R . . H34B H 0.8705 -0.0046 0.4320 0.085 Uiso 1 1 calc R . . H34A H 0.9634 0.0867 0.4539 0.085 Uiso 1 1 calc R . . C35 C 0.8205(3) 0.0916(3) 0.32396(16) 0.0391(9) Uani 1 1 d . . . C36 C 0.9174(4) 0.0930(4) 0.26961(17) 0.0605(12) Uani 1 1 d . . . H36C H 1.0130 0.0334 0.2726 0.091 Uiso 1 1 calc R . . H36B H 0.9331 0.1763 0.2637 0.091 Uiso 1 1 calc R . . H36A H 0.8686 0.0701 0.2374 0.091 Uiso 1 1 calc R . . C37 C 0.7887(4) -0.0358(3) 0.3311(2) 0.0656(13) Uani 1 1 d . . . H37C H 0.8819 -0.0986 0.3340 0.098 Uiso 1 1 calc R . . H37B H 0.7395 -0.0545 0.2981 0.098 Uiso 1 1 calc R . . H37A H 0.7242 -0.0365 0.3656 0.098 Uiso 1 1 calc R . . S3A S 0.7580(2) -0.0323(4) 0.11997(15) 0.0453(7) Uani 0.727(6) 1 d PD . . C44B C 0.748(2) 0.000(4) 0.1236(15) 0.08(2) Uani 0.273(6) 1 d PD . . S3B S 0.6856(12) -0.0771(11) 0.0711(5) 0.067(3) Uani 0.273(6) 1 d PD . . C44A C 0.6595(16) -0.0800(18) 0.0644(8) 0.071(6) Uani 0.727(6) 1 d PD . . O31A O -0.1781(6) 0.4273(6) 0.1022(3) 0.052(2) Uani 0.427(7) 1 d P . . O31B O -0.0463(5) 0.4775(5) 0.2709(2) 0.066(2) Uani 0.573(7) 1 d P . . N31 N -0.1878(3) 0.4393(3) 0.14910(18) 0.0520(9) Uani 1 1 d . . . N32 N -0.1215(3) 0.4730(3) 0.23437(16) 0.0445(8) Uani 1 1 d . . . C41 C 0.6137(4) 0.0766(4) 0.14891(18) 0.0484(10) Uani 1 1 d D . . H41 H 0.628(4) 0.120(4) 0.1821(18) 0.066(13) Uiso 1 1 d . . . C42 C 0.4853(3) 0.0828(3) 0.12214(15) 0.0350(8) Uani 1 1 d . . . C43 C 0.5113(4) -0.0025(3) 0.07711(17) 0.0428(9) Uani 1 1 d D . . H43 H 0.440(4) -0.011(3) 0.0511(17) 0.060(12) Uiso 1 1 d . . . C45 C 0.3394(3) 0.1659(3) 0.13996(15) 0.0324(8) Uani 1 1 d . . . C46 C 0.2111(4) 0.1574(3) 0.11415(17) 0.0469(10) Uani 1 1 d . . . H46A H 0.2178 0.0969 0.0853 0.056 Uiso 1 1 calc R . . C47 C 0.0765(4) 0.2351(3) 0.13004(16) 0.0450(10) Uani 1 1 d . . . H47A H -0.0086 0.2270 0.1122 0.054 Uiso 1 1 calc R . . C48 C 0.0618(3) 0.3246(3) 0.17120(15) 0.0323(8) Uani 1 1 d . . . C49 C 0.1872(3) 0.3319(3) 0.19808(16) 0.0393(9) Uani 1 1 d . . . H49A H 0.1797 0.3912 0.2275 0.047 Uiso 1 1 calc R . . C50 C 0.3233(3) 0.2526(3) 0.18200(16) 0.0387(9) Uani 1 1 d . . . H50A H 0.4078 0.2589 0.2008 0.046 Uiso 1 1 calc R . . C51 C -0.0827(3) 0.4119(3) 0.18574(18) 0.0400(9) Uani 1 1 d . . . C52 C -0.3209(4) 0.5275(3) 0.17532(18) 0.0485(10) Uani 1 1 d . . . C53 C -0.3583(5) 0.6365(5) 0.1346(2) 0.0903(18) Uani 1 1 d . . . H53C H -0.4460 0.6976 0.1503 0.135 Uiso 1 1 calc R . . H53B H -0.3784 0.6067 0.0978 0.135 Uiso 1 1 calc R . . H53A H -0.2745 0.6750 0.1296 0.135 Uiso 1 1 calc R . . C54 C -0.4454(4) 0.4600(4) 0.1791(2) 0.0655(13) Uani 1 1 d . . . H54C H -0.5362 0.5153 0.1962 0.098 Uiso 1 1 calc R . . H54B H -0.4174 0.3860 0.2026 0.098 Uiso 1 1 calc R . . H54A H -0.4625 0.4356 0.1409 0.098 Uiso 1 1 calc R . . C55 C -0.2718(3) 0.5588(3) 0.23391(18) 0.0477(10) Uani 1 1 d . . . C56 C -0.2536(5) 0.6911(4) 0.2419(3) 0.0910(18) Uani 1 1 d . . . H56C H -0.3506 0.7501 0.2418 0.137 Uiso 1 1 calc R . . H56B H -0.1877 0.7106 0.2108 0.137 Uiso 1 1 calc R . . H56A H -0.2109 0.6969 0.2782 0.137 Uiso 1 1 calc R . . C57 C -0.3659(4) 0.5288(4) 0.2857(2) 0.0689(13) Uani 1 1 d . . . H57C H -0.4655 0.5838 0.2863 0.103 Uiso 1 1 calc R . . H57B H -0.3199 0.5412 0.3205 0.103 Uiso 1 1 calc R . . H57A H -0.3723 0.4424 0.2834 0.103 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 0.0704(7) 0.0739(8) 0.0478(8) -0.0081(6) -0.0070(5) -0.0236(6) O1 0.086(2) 0.095(2) 0.055(2) -0.0047(16) 0.0108(16) -0.0624(18) N1 0.063(2) 0.055(2) 0.038(2) -0.0007(15) 0.0080(15) -0.0404(17) N2 0.0560(19) 0.0468(18) 0.037(2) 0.0066(14) -0.0069(15) -0.0226(15) C1 0.054(2) 0.044(2) 0.031(2) 0.0021(16) -0.0016(16) -0.0170(17) C2 0.0275(16) 0.0312(18) 0.029(2) 0.0000(15) 0.0028(14) -0.0046(14) C3 0.054(2) 0.044(2) 0.036(3) 0.0104(17) -0.0052(17) -0.0140(17) C4 0.0401(19) 0.066(3) 0.018(2) 0.0138(17) 0.0035(15) 0.0022(18) C5 0.0254(16) 0.0303(18) 0.028(2) 0.0024(14) -0.0006(13) -0.0034(14) C6 0.0372(18) 0.0359(19) 0.026(2) 0.0068(15) 0.0043(15) -0.0092(15) C7 0.0361(18) 0.0318(18) 0.031(2) 0.0037(15) 0.0012(15) -0.0130(14) C8 0.0290(16) 0.0272(17) 0.027(2) 0.0021(14) -0.0006(14) -0.0050(13) C9 0.051(2) 0.0369(19) 0.023(2) 0.0067(15) -0.0015(15) -0.0208(16) C10 0.045(2) 0.0350(19) 0.032(2) 0.0043(16) -0.0014(16) -0.0175(16) C11 0.0251(16) 0.0255(17) 0.032(2) 0.0017(14) 0.0001(14) -0.0035(13) C12 0.0395(18) 0.043(2) 0.023(2) -0.0054(15) -0.0008(14) -0.0155(16) C13 0.041(2) 0.065(3) 0.080(3) -0.021(2) -0.007(2) -0.021(2) C14 0.063(2) 0.038(2) 0.051(3) 0.0055(17) -0.019(2) -0.0137(18) C15 0.0366(18) 0.0362(19) 0.029(2) 0.0024(15) -0.0080(15) -0.0099(15) C16 0.066(3) 0.059(3) 0.055(3) 0.021(2) -0.017(2) -0.017(2) C17 0.055(2) 0.068(3) 0.055(3) 0.002(2) 0.008(2) -0.022(2) S2A 0.0379(11) 0.0567(13) 0.065(2) 0.0122(12) 0.0084(11) 0.0066(9) C24B 0.19(4) 0.13(3) 0.036(18) -0.014(17) -0.012(18) -0.03(2) S2B 0.084(5) 0.047(4) 0.064(5) -0.017(4) 0.031(4) -0.010(3) C24A 0.064(8) 0.093(12) 0.076(11) 0.038(8) -0.022(7) -0.040(7) O2 0.0550(17) 0.095(2) 0.047(2) -0.0242(16) -0.0184(14) 0.0225(16) N21 0.0388(16) 0.0408(17) 0.034(2) -0.0015(14) -0.0061(14) 0.0021(13) N22 0.0324(15) 0.0408(17) 0.037(2) 0.0056(13) -0.0039(13) -0.0036(13) C21 0.042(2) 0.044(2) 0.050(3) -0.004(2) -0.001(2) 0.0076(18) C22 0.0397(19) 0.0269(18) 0.038(2) 0.0062(16) 0.0047(16) -0.0071(15) C23 0.045(2) 0.048(2) 0.047(3) -0.006(2) 0.002(2) -0.0069(19) C25 0.0328(17) 0.0257(17) 0.032(2) 0.0035(14) 0.0011(15) -0.0072(14) C26 0.0302(18) 0.046(2) 0.040(2) -0.0025(17) -0.0051(15) -0.0040(16) C27 0.0333(19) 0.044(2) 0.037(2) -0.0083(17) -0.0024(16) -0.0082(16) C28 0.0323(17) 0.0279(17) 0.028(2) 0.0027(14) -0.0013(14) -0.0066(14) C29 0.042(2) 0.050(2) 0.036(2) -0.0033(18) -0.0116(17) 0.0014(17) C30 0.049(2) 0.046(2) 0.034(2) -0.0070(17) -0.0050(17) 0.0004(18) C31 0.0324(18) 0.0300(18) 0.032(2) 0.0070(15) -0.0016(15) -0.0078(14) C32 0.0306(18) 0.0366(19) 0.037(2) 0.0115(16) -0.0002(15) -0.0004(15) C33 0.042(2) 0.061(3) 0.064(3) 0.006(2) -0.0029(19) -0.0155(19) C34 0.051(2) 0.058(3) 0.050(3) 0.017(2) -0.0018(19) 0.0055(19) C35 0.0304(18) 0.037(2) 0.045(3) 0.0023(17) -0.0022(16) -0.0004(15) C36 0.045(2) 0.085(3) 0.042(3) -0.001(2) 0.0056(19) 0.000(2) C37 0.053(2) 0.037(2) 0.105(4) -0.006(2) -0.007(2) -0.0052(18) S3A 0.0338(10) 0.0507(15) 0.0419(14) 0.0004(8) 0.0012(8) 0.0071(7) C44B 0.11(3) 0.08(3) 0.048(18) -0.009(15) -0.038(17) 0.009(16) S3B 0.097(6) 0.040(4) 0.062(6) -0.006(4) 0.023(5) -0.019(4) C44A 0.079(7) 0.075(10) 0.071(8) 0.034(6) -0.039(6) -0.037(6) O31A 0.052(4) 0.069(4) 0.034(5) 0.000(3) -0.019(3) -0.006(3) O31B 0.044(3) 0.100(4) 0.033(3) -0.011(3) -0.014(2) 0.028(3) N31 0.0297(17) 0.068(2) 0.057(3) 0.0171(19) -0.0146(17) -0.0067(15) N32 0.0249(15) 0.0445(19) 0.061(3) -0.0058(17) -0.0021(16) -0.0019(13) C41 0.039(2) 0.051(2) 0.048(3) -0.006(2) -0.0120(19) 0.0051(18) C42 0.0377(19) 0.0293(18) 0.037(2) 0.0101(16) 0.0016(16) -0.0078(15) C43 0.042(2) 0.043(2) 0.044(3) -0.0006(18) 0.0026(18) -0.0130(18) C45 0.0339(18) 0.0305(18) 0.035(2) 0.0078(15) -0.0042(15) -0.0112(15) C46 0.044(2) 0.047(2) 0.047(3) -0.0086(18) -0.0143(18) -0.0025(18) C47 0.0341(19) 0.048(2) 0.053(3) -0.0010(19) -0.0191(17) -0.0041(17) C48 0.0277(17) 0.0310(18) 0.039(2) 0.0117(15) -0.0061(15) -0.0087(14) C49 0.0288(18) 0.0317(19) 0.056(3) -0.0030(16) -0.0056(16) -0.0036(15) C50 0.0259(17) 0.038(2) 0.053(3) -0.0021(17) -0.0078(16) -0.0092(15) C51 0.0288(18) 0.0277(19) 0.066(3) 0.0142(18) -0.0055(18) -0.0109(15) C52 0.0275(18) 0.050(2) 0.071(3) 0.025(2) -0.0158(18) -0.0119(17) C53 0.053(3) 0.094(4) 0.114(5) 0.062(3) -0.015(3) 0.000(3) C54 0.041(2) 0.084(3) 0.082(4) 0.012(2) -0.015(2) -0.032(2) C55 0.0252(18) 0.032(2) 0.083(3) -0.0011(19) -0.0020(18) -0.0033(15) C56 0.070(3) 0.042(3) 0.163(6) -0.002(3) -0.016(3) -0.015(2) C57 0.036(2) 0.091(3) 0.078(4) -0.018(3) 0.014(2) -0.016(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 C4 1.675(4) . ? S1 C1 1.711(4) . ? O1 N1 1.287(4) . ? N1 C11 1.362(4) . ? N1 C12 1.474(4) . ? N2 C11 1.299(4) . ? N2 C15 1.501(4) . ? C1 C2 1.365(4) . ? C1 H1A 0.9500 . ? C2 C3 1.416(5) . ? C2 C5 1.482(5) . ? C3 C4 1.416(5) . ? C3 H3A 0.9500 . ? C4 H4A 0.9500 . ? C5 C6 1.390(4) . ? C5 C10 1.396(5) . ? C6 C7 1.387(5) . ? C6 H6A 0.9500 . ? C7 C8 1.387(4) . ? C7 H7A 0.9500 . ? C8 C9 1.391(4) . ? C8 C11 1.487(4) . ? C9 C10 1.378(5) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C12 C14 1.513(5) . ? C12 C13 1.528(4) . ? C12 C15 1.548(5) . ? C13 H13C 0.9800 . ? C13 H13B 0.9800 . ? C13 H13A 0.9800 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C14 H14A 0.9800 . ? C15 C17 1.516(5) . ? C15 C16 1.535(5) . ? C16 H16C 0.9800 . ? C16 H16B 0.9800 . ? C16 H16A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C17 H17A 0.9800 . ? S2A S2B 1.592(10) . ? S2A C21 1.673(4) . ? S2A C24A 1.779(14) . ? C24B C21 1.432(18) . ? C24B S2B 1.746(19) . ? C24B C24A 1.92(3) . ? S2B C23 1.604(9) . ? C24A C23 1.478(14) . ? O2 N21 1.269(4) . ? N21 C31 1.390(4) . ? N21 C35 1.486(4) . ? N22 C31 1.298(4) . ? N22 C32 1.495(4) . ? C21 C22 1.391(5) . ? C21 H21 0.98(4) . ? C22 C23 1.395(5) . ? C22 C25 1.476(4) . ? C23 H23 0.86(4) . ? C25 C30 1.392(5) . ? C25 C26 1.394(5) . ? C26 C27 1.377(4) . ? C26 H26A 0.9500 . ? C27 C28 1.392(4) . ? C27 H27A 0.9500 . ? C28 C29 1.381(5) . ? C28 C31 1.478(4) . ? C29 C30 1.381(5) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C32 C34 1.523(5) . ? C32 C33 1.533(5) . ? C32 C35 1.557(5) . ? C33 H33C 0.9800 . ? C33 H33B 0.9800 . ? C33 H33A 0.9800 . ? C34 H34C 0.9800 . ? C34 H34B 0.9800 . ? C34 H34A 0.9800 . ? C35 C36 1.518(5) . ? C35 C37 1.522(5) . ? C36 H36C 0.9800 . ? C36 H36B 0.9800 . ? C36 H36A 0.9800 . ? C37 H37C 0.9800 . ? C37 H37B 0.9800 . ? C37 H37A 0.9800 . ? S3A S3B 1.526(14) . ? S3A C41 1.685(4) . ? S3A C44A 1.811(14) . ? C44B C41 1.423(19) . ? C44B S3B 1.729(19) . ? C44B C44A 2.00(3) . ? S3B C43 1.634(11) . ? C44A C43 1.454(14) . ? O31A N31 1.111(6) . ? O31B N32 1.159(5) . ? N31 C51 1.333(5) . ? N31 C52 1.483(5) . ? N32 C51 1.322(5) . ? N32 C55 1.493(4) . ? C41 C42 1.382(5) . ? C41 H41 0.96(4) . ? C42 C43 1.401(5) . ? C42 C45 1.483(4) . ? C43 H43 0.96(4) . ? C45 C50 1.367(5) . ? C45 C46 1.406(4) . ? C46 C47 1.370(5) . ? C46 H46A 0.9500 . ? C47 C48 1.374(5) . ? C47 H47A 0.9500 . ? C48 C49 1.392(4) . ? C48 C51 1.477(5) . ? C49 C50 1.388(4) . ? C49 H49A 0.9500 . ? C50 H50A 0.9500 . ? C52 C53 1.526(5) . ? C52 C54 1.527(5) . ? C52 C55 1.557(6) . ? C53 H53C 0.9800 . ? C53 H53B 0.9800 . ? C53 H53A 0.9800 . ? C54 H54C 0.9800 . ? C54 H54B 0.9800 . ? C54 H54A 0.9800 . ? C55 C57 1.535(6) . ? C55 C56 1.537(5) . ? C56 H56C 0.9800 . ? C56 H56B 0.9800 . ? C56 H56A 0.9800 . ? C57 H57C 0.9800 . ? C57 H57B 0.9800 . ? C57 H57A 0.9800 . ? 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 C4 S1 C1 93.16(18) . . ? O1 N1 C11 125.7(3) . . ? O1 N1 C12 122.7(3) . . ? C11 N1 C12 111.6(3) . . ? C11 N2 C15 108.0(3) . . ? C2 C1 S1 112.8(3) . . ? C2 C1 H1A 123.6 . . ? S1 C1 H1A 123.6 . . ? C1 C2 C3 110.6(3) . . ? C1 C2 C5 124.0(3) . . ? C3 C2 C5 125.4(3) . . ? C4 C3 C2 113.4(3) . . ? C4 C3 H3A 123.3 . . ? C2 C3 H3A 123.3 . . ? C3 C4 S1 110.0(3) . . ? C3 C4 H4A 125.0 . . ? S1 C4 H4A 125.0 . . ? C6 C5 C10 117.7(3) . . ? C6 C5 C2 121.8(3) . . ? C10 C5 C2 120.5(3) . . ? C7 C6 C5 121.9(3) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C7 C8 C9 118.8(3) . . ? C7 C8 C11 124.3(3) . . ? C9 C8 C11 116.7(3) . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C5 120.8(3) . . ? C9 C10 H10A 119.6 . . ? C5 C10 H10A 119.6 . . ? N2 C11 N1 112.5(3) . . ? N2 C11 C8 121.9(3) . . ? N1 C11 C8 125.5(3) . . ? N1 C12 C14 108.2(3) . . ? N1 C12 C13 108.9(3) . . ? C14 C12 C13 109.9(3) . . ? N1 C12 C15 98.7(2) . . ? C14 C12 C15 115.0(3) . . ? C13 C12 C15 115.2(3) . . ? C12 C13 H13C 109.5 . . ? C12 C13 H13B 109.5 . . ? H13C C13 H13B 109.5 . . ? C12 C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? C12 C14 H14C 109.5 . . ? C12 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C12 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? N2 C15 C17 107.4(3) . . ? N2 C15 C16 104.5(3) . . ? C17 C15 C16 108.5(3) . . ? N2 C15 C12 104.7(3) . . ? C17 C15 C12 115.5(3) . . ? C16 C15 C12 115.4(3) . . ? C15 C16 H16C 109.5 . . ? C15 C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C15 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? C15 C17 H17C 109.5 . . ? C15 C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C15 C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? S2B S2A C21 100.3(3) . . ? S2B S2A C24A 3.4(8) . . ? C21 S2A C24A 97.4(5) . . ? C21 C24B S2B 103.8(13) . . ? C21 C24B C24A 100.5(13) . . ? S2B C24B C24A 3.8(7) . . ? S2A S2B C23 104.3(4) . . ? S2A S2B C24B 7.8(8) . . ? C23 S2B C24B 96.8(7) . . ? C23 C24A S2A 101.2(8) . . ? C23 C24A C24B 94.3(10) . . ? S2A C24A C24B 7.3(8) . . ? O2 N21 C31 126.8(3) . . ? O2 N21 C35 122.1(3) . . ? C31 N21 C35 110.8(3) . . ? C31 N22 C32 109.6(3) . . ? C22 C21 C24B 115.9(9) . . ? C22 C21 S2A 112.2(3) . . ? C24B C21 S2A 4.7(13) . . ? C22 C21 H21 124(2) . . ? C24B C21 H21 120(3) . . ? S2A C21 H21 124(2) . . ? C21 C22 C23 110.5(3) . . ? C21 C22 C25 124.1(3) . . ? C23 C22 C25 125.4(3) . . ? C22 C23 C24A 118.7(7) . . ? C22 C23 S2B 112.7(4) . . ? C24A C23 S2B 6.3(9) . . ? C22 C23 H23 126(3) . . ? C24A C23 H23 115(3) . . ? S2B C23 H23 121(3) . . ? C30 C25 C26 117.0(3) . . ? C30 C25 C22 121.3(3) . . ? C26 C25 C22 121.7(3) . . ? C27 C26 C25 122.0(3) . . ? C27 C26 H26A 119.0 . . ? C25 C26 H26A 119.0 . . ? C26 C27 C28 120.6(3) . . ? C26 C27 H27A 119.7 . . ? C28 C27 H27A 119.7 . . ? C29 C28 C27 117.8(3) . . ? C29 C28 C31 118.3(3) . . ? C27 C28 C31 123.9(3) . . ? C30 C29 C28 121.6(3) . . ? C30 C29 H29A 119.2 . . ? C28 C29 H29A 119.2 . . ? C29 C30 C25 121.0(3) . . ? C29 C30 H30A 119.5 . . ? C25 C30 H30A 119.5 . . ? N22 C31 N21 112.0(3) . . ? N22 C31 C28 123.8(3) . . ? N21 C31 C28 124.2(3) . . ? N22 C32 C34 108.5(3) . . ? N22 C32 C33 105.3(3) . . ? C34 C32 C33 109.3(3) . . ? N22 C32 C35 104.8(2) . . ? C34 C32 C35 115.2(3) . . ? C33 C32 C35 113.0(3) . . ? C32 C33 H33C 109.5 . . ? C32 C33 H33B 109.5 . . ? H33C C33 H33B 109.5 . . ? C32 C33 H33A 109.5 . . ? H33C C33 H33A 109.5 . . ? H33B C33 H33A 109.5 . . ? C32 C34 H34C 109.5 . . ? C32 C34 H34B 109.5 . . ? H34C C34 H34B 109.5 . . ? C32 C34 H34A 109.5 . . ? H34C C34 H34A 109.5 . . ? H34B C34 H34A 109.5 . . ? N21 C35 C36 110.1(3) . . ? N21 C35 C37 106.3(3) . . ? C36 C35 C37 109.2(3) . . ? N21 C35 C32 99.6(2) . . ? C36 C35 C32 116.2(3) . . ? C37 C35 C32 114.6(3) . . ? C35 C36 H36C 109.5 . . ? C35 C36 H36B 109.5 . . ? H36C C36 H36B 109.5 . . ? C35 C36 H36A 109.5 . . ? H36C C36 H36A 109.5 . . ? H36B C36 H36A 109.5 . . ? C35 C37 H37C 109.5 . . ? C35 C37 H37B 109.5 . . ? H37C C37 H37B 109.5 . . ? C35 C37 H37A 109.5 . . ? H37C C37 H37A 109.5 . . ? H37B C37 H37A 109.5 . . ? S3B S3A C41 100.2(4) . . ? S3B S3A C44A 4.0(8) . . ? C41 S3A C44A 96.3(5) . . ? C41 C44B S3B 102.5(13) . . ? C41 C44B C44A 97.9(13) . . ? S3B C44B C44A 4.7(6) . . ? S3A S3B C43 106.4(5) . . ? S3A S3B C44B 10.6(14) . . ? C43 S3B C44B 98.2(8) . . ? C43 C44A S3A 101.1(9) . . ? C43 C44A C44B 93.6(10) . . ? S3A C44A C44B 9.4(12) . . ? O31A N31 C51 129.3(4) . . ? O31A N31 C52 118.1(4) . . ? C51 N31 C52 110.2(4) . . ? O31B N32 C51 127.1(3) . . ? O31B N32 C55 120.5(4) . . ? C51 N32 C55 111.5(3) . . ? C42 C41 C44B 117.6(10) . . ? C42 C41 S3A 112.3(3) . . ? C44B C41 S3A 9.3(17) . . ? C42 C41 H41 129(2) . . ? C44B C41 H41 113(2) . . ? S3A C41 H41 118(2) . . ? C41 C42 C43 110.7(3) . . ? C41 C42 C45 124.4(3) . . ? C43 C42 C45 124.9(3) . . ? C42 C43 C44A 119.5(7) . . ? C42 C43 S3B 110.2(5) . . ? C44A C43 S3B 9.3(9) . . ? C42 C43 H43 125(2) . . ? C44A C43 H43 115(2) . . ? S3B C43 H43 124(2) . . ? C50 C45 C46 117.3(3) . . ? C50 C45 C42 121.9(3) . . ? C46 C45 C42 120.8(3) . . ? C47 C46 C45 120.9(3) . . ? C47 C46 H46A 119.6 . . ? C45 C46 H46A 119.6 . . ? C46 C47 C48 121.6(3) . . ? C46 C47 H47A 119.2 . . ? C48 C47 H47A 119.2 . . ? C47 C48 C49 118.1(3) . . ? C47 C48 C51 120.9(3) . . ? C49 C48 C51 121.0(3) . . ? C50 C49 C48 120.1(3) . . ? C50 C49 H49A 119.9 . . ? C48 C49 H49A 119.9 . . ? C45 C50 C49 122.0(3) . . ? C45 C50 H50A 119.0 . . ? C49 C50 H50A 119.0 . . ? N32 C51 N31 112.8(3) . . ? N32 C51 C48 125.3(3) . . ? N31 C51 C48 122.0(4) . . ? N31 C52 C53 106.6(4) . . ? N31 C52 C54 106.6(3) . . ? C53 C52 C54 109.6(3) . . ? N31 C52 C55 103.6(3) . . ? C53 C52 C55 115.2(4) . . ? C54 C52 C55 114.3(3) . . ? C52 C53 H53C 109.5 . . ? C52 C53 H53B 109.5 . . ? H53C C53 H53B 109.5 . . ? C52 C53 H53A 109.5 . . ? H53C C53 H53A 109.5 . . ? H53B C53 H53A 109.5 . . ? C52 C54 H54C 109.5 . . ? C52 C54 H54B 109.5 . . ? H54C C54 H54B 109.5 . . ? C52 C54 H54A 109.5 . . ? H54C C54 H54A 109.5 . . ? H54B C54 H54A 109.5 . . ? N32 C55 C57 107.9(3) . . ? N32 C55 C56 107.3(3) . . ? C57 C55 C56 107.6(4) . . ? N32 C55 C52 101.6(3) . . ? C57 C55 C52 115.1(3) . . ? C56 C55 C52 116.7(4) . . ? C55 C56 H56C 109.5 . . ? C55 C56 H56B 109.5 . . ? H56C C56 H56B 109.5 . . ? C55 C56 H56A 109.5 . . ? H56C C56 H56A 109.5 . . ? H56B C56 H56A 109.5 . . ? C55 C57 H57C 109.5 . . ? C55 C57 H57B 109.5 . . ? H57C C57 H57B 109.5 . . ? C55 C57 H57A 109.5 . . ? H57C C57 H57A 109.5 . . ? H57B C57 H57A 109.5 . . ? 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 C4 S1 C1 C2 -0.3(3) . . . . ? S1 C1 C2 C3 0.0(4) . . . . ? S1 C1 C2 C5 179.9(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C5 C2 C3 C4 -179.5(3) . . . . ? C2 C3 C4 S1 -0.6(4) . . . . ? C1 S1 C4 C3 0.5(3) . . . . ? C1 C2 C5 C6 -161.6(3) . . . . ? C3 C2 C5 C6 18.3(5) . . . . ? C1 C2 C5 C10 18.1(5) . . . . ? C3 C2 C5 C10 -162.0(3) . . . . ? C10 C5 C6 C7 0.4(5) . . . . ? C2 C5 C6 C7 -179.8(3) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C6 C7 C8 C11 175.7(3) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C11 C8 C9 C10 -176.2(3) . . . . ? C8 C9 C10 C5 0.3(5) . . . . ? C6 C5 C10 C9 -0.7(5) . . . . ? C2 C5 C10 C9 179.6(3) . . . . ? C15 N2 C11 N1 6.3(4) . . . . ? C15 N2 C11 C8 -175.4(3) . . . . ? O1 N1 C11 N2 -174.3(3) . . . . ? C12 N1 C11 N2 8.5(4) . . . . ? O1 N1 C11 C8 7.4(5) . . . . ? C12 N1 C11 C8 -169.7(3) . . . . ? C7 C8 C11 N2 -166.9(3) . . . . ? C9 C8 C11 N2 9.3(4) . . . . ? C7 C8 C11 N1 11.2(5) . . . . ? C9 C8 C11 N1 -172.6(3) . . . . ? O1 N1 C12 C14 -75.4(4) . . . . ? C11 N1 C12 C14 101.9(3) . . . . ? O1 N1 C12 C13 44.2(5) . . . . ? C11 N1 C12 C13 -138.6(3) . . . . ? O1 N1 C12 C15 164.6(3) . . . . ? C11 N1 C12 C15 -18.1(3) . . . . ? C11 N2 C15 C17 -140.8(3) . . . . ? C11 N2 C15 C16 104.2(3) . . . . ? C11 N2 C15 C12 -17.5(3) . . . . ? N1 C12 C15 N2 20.3(3) . . . . ? C14 C12 C15 N2 -94.6(3) . . . . ? C13 C12 C15 N2 136.1(3) . . . . ? N1 C12 C15 C17 138.2(3) . . . . ? C14 C12 C15 C17 23.3(4) . . . . ? C13 C12 C15 C17 -106.1(3) . . . . ? N1 C12 C15 C16 -93.9(3) . . . . ? C14 C12 C15 C16 151.2(3) . . . . ? C13 C12 C15 C16 21.9(4) . . . . ? C21 S2A S2B C23 -0.9(7) . . . . ? C24A S2A S2B C23 27(18) . . . . ? C21 S2A S2B C24B -17(11) . . . . ? C24A S2A S2B C24B 11(22) . . . . ? C21 C24B S2B S2A 159(13) . . . . ? C24A C24B S2B S2A -171(18) . . . . ? C21 C24B S2B C23 -5(2) . . . . ? C24A C24B S2B C23 25(14) . . . . ? S2B S2A C24A C23 -151(19) . . . . ? C21 S2A C24A C23 1.5(11) . . . . ? S2B S2A C24A C24B -170(21) . . . . ? C21 S2A C24A C24B -17(10) . . . . ? C21 C24B C24A C23 -2(2) . . . . ? S2B C24B C24A C23 -153(16) . . . . ? C21 C24B C24A S2A 159(12) . . . . ? S2B C24B C24A S2A 8(17) . . . . ? S2B C24B C21 C22 5(3) . . . . ? C24A C24B C21 C22 3(3) . . . . ? S2B C24B C21 S2A -33(18) . . . . ? C24A C24B C21 S2A -35(18) . . . . ? S2B S2A C21 C22 0.5(6) . . . . ? C24A S2A C21 C22 -1.1(8) . . . . ? S2B S2A C21 C24B 143(20) . . . . ? C24A S2A C21 C24B 142(20) . . . . ? C24B C21 C22 C23 -3(2) . . . . ? S2A C21 C22 C23 0.3(5) . . . . ? C24B C21 C22 C25 176.5(19) . . . . ? S2A C21 C22 C25 179.7(3) . . . . ? C21 C22 C23 C24A 1.0(11) . . . . ? C25 C22 C23 C24A -178.4(10) . . . . ? C21 C22 C23 S2B -1.0(7) . . . . ? C25 C22 C23 S2B 179.6(5) . . . . ? S2A C24A C23 C22 -1.7(14) . . . . ? C24B C24A C23 C22 0.7(18) . . . . ? S2A C24A C23 S2B 15(10) . . . . ? C24B C24A C23 S2B 17(11) . . . . ? S2A S2B C23 C22 1.2(8) . . . . ? C24B S2B C23 C22 3.4(16) . . . . ? S2A S2B C23 C24A -163(12) . . . . ? C24B S2B C23 C24A -161(12) . . . . ? C21 C22 C25 C30 -169.7(4) . . . . ? C23 C22 C25 C30 9.6(5) . . . . ? C21 C22 C25 C26 8.2(5) . . . . ? C23 C22 C25 C26 -172.4(4) . . . . ? C30 C25 C26 C27 -0.5(5) . . . . ? C22 C25 C26 C27 -178.5(3) . . . . ? C25 C26 C27 C28 -0.2(5) . . . . ? C26 C27 C28 C29 0.4(5) . . . . ? C26 C27 C28 C31 179.9(3) . . . . ? C27 C28 C29 C30 0.0(5) . . . . ? C31 C28 C29 C30 -179.6(3) . . . . ? C28 C29 C30 C25 -0.7(6) . . . . ? C26 C25 C30 C29 0.9(5) . . . . ? C22 C25 C30 C29 178.9(3) . . . . ? C32 N22 C31 N21 4.4(4) . . . . ? C32 N22 C31 C28 -174.8(3) . . . . ? O2 N21 C31 N22 -178.2(3) . . . . ? C35 N21 C31 N22 8.4(4) . . . . ? O2 N21 C31 C28 0.9(5) . . . . ? C35 N21 C31 C28 -172.5(3) . . . . ? C29 C28 C31 N22 4.4(5) . . . . ? C27 C28 C31 N22 -175.1(3) . . . . ? C29 C28 C31 N21 -174.6(3) . . . . ? C27 C28 C31 N21 5.9(5) . . . . ? C31 N22 C32 C34 -138.0(3) . . . . ? C31 N22 C32 C33 105.0(3) . . . . ? C31 N22 C32 C35 -14.4(4) . . . . ? O2 N21 C35 C36 47.5(5) . . . . ? C31 N21 C35 C36 -138.7(3) . . . . ? O2 N21 C35 C37 -70.6(4) . . . . ? C31 N21 C35 C37 103.2(3) . . . . ? O2 N21 C35 C32 170.1(3) . . . . ? C31 N21 C35 C32 -16.1(3) . . . . ? N22 C32 C35 N21 17.5(3) . . . . ? C34 C32 C35 N21 136.6(3) . . . . ? C33 C32 C35 N21 -96.7(3) . . . . ? N22 C32 C35 C36 135.6(3) . . . . ? C34 C32 C35 C36 -105.3(4) . . . . ? C33 C32 C35 C36 21.4(4) . . . . ? N22 C32 C35 C37 -95.5(3) . . . . ? C34 C32 C35 C37 23.7(4) . . . . ? C33 C32 C35 C37 150.4(3) . . . . ? C41 S3A S3B C43 -3.6(9) . . . . ? C44A S3A S3B C43 11(18) . . . . ? C41 S3A S3B C44B 37(7) . . . . ? C44A S3A S3B C44B 52(20) . . . . ? C41 C44B S3B S3A -134(9) . . . . ? C44A C44B S3B S3A -142(15) . . . . ? C41 C44B S3B C43 7(3) . . . . ? C44A C44B S3B C43 -1(14) . . . . ? S3B S3A C44A C43 -168(19) . . . . ? C41 S3A C44A C43 -2.4(12) . . . . ? S3B S3A C44A C44B -130(20) . . . . ? C41 S3A C44A C44B 36(7) . . . . ? C41 C44B C44A C43 7(3) . . . . ? S3B C44B C44A C43 179(100) . . . . ? C41 C44B C44A S3A -136(9) . . . . ? S3B C44B C44A S3A 36(15) . . . . ? S3B C44B C41 C42 -9(3) . . . . ? C44A C44B C41 C42 -8(3) . . . . ? S3B C44B C41 S3A 48(8) . . . . ? C44A C44B C41 S3A 49(8) . . . . ? S3B S3A C41 C42 3.2(7) . . . . ? C44A S3A C41 C42 2.2(8) . . . . ? S3B S3A C41 C44B -123(10) . . . . ? C44A S3A C41 C44B -124(10) . . . . ? C44B C41 C42 C43 7(2) . . . . ? S3A C41 C42 C43 -1.1(5) . . . . ? C44B C41 C42 C45 -174(2) . . . . ? S3A C41 C42 C45 177.2(3) . . . . ? C41 C42 C43 C44A -0.9(12) . . . . ? C45 C42 C43 C44A -179.2(11) . . . . ? C41 C42 C43 S3B -1.4(7) . . . . ? C45 C42 C43 S3B -179.7(6) . . . . ? S3A C44A C43 C42 2.3(15) . . . . ? C44B C44A C43 C42 -3.5(19) . . . . ? S3A C44A C43 S3B 5(8) . . . . ? C44B C44A C43 S3B -1(8) . . . . ? S3A S3B C43 C42 3.5(10) . . . . ? C44B S3B C43 C42 -3.4(18) . . . . ? S3A S3B C43 C44A -174(10) . . . . ? C44B S3B C43 C44A 179(10) . . . . ? C41 C42 C45 C50 6.2(5) . . . . ? C43 C42 C45 C50 -175.8(4) . . . . ? C41 C42 C45 C46 -173.3(4) . . . . ? C43 C42 C45 C46 4.7(5) . . . . ? C50 C45 C46 C47 1.3(5) . . . . ? C42 C45 C46 C47 -179.1(3) . . . . ? C45 C46 C47 C48 0.6(6) . . . . ? C46 C47 C48 C49 -2.1(6) . . . . ? C46 C47 C48 C51 176.8(3) . . . . ? C47 C48 C49 C50 1.9(5) . . . . ? C51 C48 C49 C50 -177.0(3) . . . . ? C46 C45 C50 C49 -1.5(5) . . . . ? C42 C45 C50 C49 178.9(3) . . . . ? C48 C49 C50 C45 0.0(5) . . . . ? O31B N32 C51 N31 -170.8(5) . . . . ? C55 N32 C51 N31 -1.6(4) . . . . ? O31B N32 C51 C48 7.7(7) . . . . ? C55 N32 C51 C48 176.8(3) . . . . ? O31A N31 C51 N32 159.3(6) . . . . ? C52 N31 C51 N32 -2.3(4) . . . . ? O31A N31 C51 C48 -19.2(7) . . . . ? C52 N31 C51 C48 179.2(3) . . . . ? C47 C48 C51 N32 157.4(4) . . . . ? C49 C48 C51 N32 -23.7(5) . . . . ? C47 C48 C51 N31 -24.3(5) . . . . ? C49 C48 C51 N31 154.6(3) . . . . ? O31A N31 C52 C53 -37.0(6) . . . . ? C51 N31 C52 C53 127.0(4) . . . . ? O31A N31 C52 C54 80.0(6) . . . . ? C51 N31 C52 C54 -116.1(3) . . . . ? O31A N31 C52 C55 -159.0(5) . . . . ? C51 N31 C52 C55 5.0(4) . . . . ? O31B N32 C55 C57 -64.2(5) . . . . ? C51 N32 C55 C57 125.8(3) . . . . ? O31B N32 C55 C56 51.4(6) . . . . ? C51 N32 C55 C56 -118.5(4) . . . . ? O31B N32 C55 C52 174.4(5) . . . . ? C51 N32 C55 C52 4.5(4) . . . . ? N31 C52 C55 N32 -5.4(3) . . . . ? C53 C52 C55 N32 -121.4(3) . . . . ? C54 C52 C55 N32 110.3(3) . . . . ? N31 C52 C55 C57 -121.5(3) . . . . ? C53 C52 C55 C57 122.4(4) . . . . ? C54 C52 C55 C57 -5.9(5) . . . . ? N31 C52 C55 C56 110.9(3) . . . . ? C53 C52 C55 C56 -5.1(5) . . . . ? C54 C52 C55 C56 -133.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.630 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.047 data_compound3 _database_code_CSD 199927 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 N3 O2' _chemical_formula_weight 272.32 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 10.1447(8) _cell_length_b 13.1725(8) _cell_length_c 11.4922(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.697(8) _cell_angle_gamma 90.00 _cell_volume 1395.24(17) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.87 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10256 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.87 _reflns_number_total 2704 _reflns_number_gt 1961 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (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^)+(0.1000P)^2^] 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 2704 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 0.654 _refine_ls_restrained_S_all 0.654 _refine_ls_shift/su_max 0.000 _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 O1 O 0.38811(12) -0.08098(7) 0.13369(9) 0.0375(3) Uani 1 1 d . . . O2 O 0.59305(10) 0.19748(7) 0.39388(9) 0.0316(2) Uani 1 1 d . . . N1 N 0.41536(11) 0.01027(8) 0.17793(10) 0.0245(2) Uani 1 1 d . . . N2 N 0.51358(11) 0.14197(7) 0.29881(10) 0.0227(2) Uani 1 1 d . . . N3 N 0.92842(12) -0.20971(8) 0.65571(10) 0.0265(3) Uani 1 1 d . . . H3N H 0.9353(19) -0.2770(14) 0.6699(17) 0.045(5) Uiso 1 1 d . . . C1 C 0.51533(13) 0.03915(9) 0.29337(12) 0.0230(3) Uani 1 1 d . . . C2 C 0.32283(14) 0.09652(9) 0.10152(12) 0.0250(3) Uani 1 1 d . . . C3 C 0.29782(18) 0.08563(12) -0.03845(13) 0.0359(3) Uani 1 1 d . . . H3A H 0.2432(19) 0.1463(14) -0.0856(17) 0.047(5) Uiso 1 1 d . . . H3B H 0.393(2) 0.0826(13) -0.0489(17) 0.045(5) Uiso 1 1 d . . . H3C H 0.237(2) 0.0240(15) -0.0722(18) 0.053(5) Uiso 1 1 d . . . C4 C 0.17882(16) 0.08848(12) 0.11387(16) 0.0360(3) Uani 1 1 d . . . H4A H 0.1943(19) 0.0918(12) 0.2038(18) 0.044(5) Uiso 1 1 d . . . H4B H 0.1362(19) 0.0221(14) 0.0777(17) 0.047(5) Uiso 1 1 d . . . H4C H 0.112(2) 0.1434(14) 0.0659(17) 0.046(5) Uiso 1 1 d . . . C5 C 0.41772(13) 0.18926(9) 0.17290(11) 0.0237(3) Uani 1 1 d . . . C6 C 0.51891(16) 0.22775(11) 0.11422(15) 0.0330(3) Uani 1 1 d . . . H6A H 0.5728(18) 0.1697(13) 0.0965(16) 0.041(4) Uiso 1 1 d . . . H6B H 0.5866(19) 0.2773(13) 0.1727(17) 0.041(4) Uiso 1 1 d . . . H6C H 0.4614(17) 0.2641(12) 0.0316(16) 0.038(4) Uiso 1 1 d . . . C7 C 0.33540(15) 0.27748(10) 0.19671(13) 0.0278(3) Uani 1 1 d . . . H7A H 0.4015(17) 0.3320(12) 0.2421(15) 0.031(4) Uiso 1 1 d . . . H7B H 0.2649(19) 0.3038(12) 0.1123(18) 0.044(5) Uiso 1 1 d . . . H7C H 0.2851(18) 0.2572(13) 0.2491(17) 0.045(4) Uiso 1 1 d . . . C8 C 0.61568(13) -0.02730(9) 0.39287(11) 0.0226(3) Uani 1 1 d . . . C9 C 0.57367(15) -0.12781(10) 0.40722(12) 0.0253(3) Uani 1 1 d . . . H9 H 0.4719(17) -0.1488(11) 0.3570(14) 0.028(4) Uiso 1 1 d . . . C10 C 0.67051(14) -0.19485(9) 0.49204(12) 0.0262(3) Uani 1 1 d . . . H10 H 0.6414(17) -0.2655(12) 0.5006(14) 0.031(4) Uiso 1 1 d . . . C11 C 0.81126(14) -0.16041(9) 0.56569(11) 0.0228(3) Uani 1 1 d . . . C12 C 1.04254(15) -0.14260(10) 0.70547(13) 0.0290(3) Uani 1 1 d . . . H12 H 1.1356(18) -0.1679(12) 0.7724(16) 0.037(4) Uiso 1 1 d . . . C13 C 1.00132(14) -0.04966(10) 0.65019(13) 0.0276(3) Uani 1 1 d . . . H13 H 1.0660(18) 0.0106(12) 0.6713(16) 0.038(4) Uiso 1 1 d . . . C14 C 0.85355(14) -0.05884(9) 0.55899(12) 0.0229(3) Uani 1 1 d . . . C15 C 0.75418(13) 0.00740(9) 0.47045(12) 0.0230(3) Uani 1 1 d . . . H15 H 0.7840(16) 0.0761(11) 0.4619(14) 0.029(4) Uiso 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 O1 0.0450(6) 0.0214(5) 0.0294(5) -0.0058(4) -0.0009(5) 0.0002(4) O2 0.0316(5) 0.0240(5) 0.0261(5) -0.0042(4) -0.0008(4) -0.0028(4) N1 0.0255(6) 0.0212(5) 0.0205(5) -0.0020(4) 0.0035(5) 0.0003(4) N2 0.0214(5) 0.0209(5) 0.0202(5) -0.0018(4) 0.0032(4) -0.0008(4) N3 0.0298(6) 0.0229(6) 0.0241(5) 0.0036(4) 0.0086(5) 0.0042(4) C1 0.0216(6) 0.0233(6) 0.0219(6) -0.0001(5) 0.0069(5) -0.0010(5) C2 0.0238(6) 0.0243(6) 0.0213(6) 0.0005(5) 0.0039(5) 0.0045(5) C3 0.0425(9) 0.0350(8) 0.0212(7) -0.0010(6) 0.0044(6) 0.0084(7) C4 0.0248(7) 0.0359(8) 0.0417(9) -0.0064(7) 0.0084(7) -0.0021(6) C5 0.0230(6) 0.0243(6) 0.0196(6) 0.0019(5) 0.0047(5) 0.0026(5) C6 0.0329(8) 0.0346(8) 0.0331(8) 0.0055(6) 0.0154(7) 0.0011(6) C7 0.0297(7) 0.0249(7) 0.0247(7) 0.0009(5) 0.0072(6) 0.0048(6) C8 0.0239(6) 0.0223(6) 0.0202(6) -0.0002(5) 0.0077(5) -0.0001(5) C9 0.0267(7) 0.0256(6) 0.0200(6) -0.0009(5) 0.0061(5) -0.0044(5) C10 0.0331(7) 0.0219(6) 0.0213(6) 0.0004(5) 0.0092(6) -0.0044(5) C11 0.0273(6) 0.0218(6) 0.0194(6) 0.0005(5) 0.0099(5) 0.0017(5) C12 0.0236(7) 0.0326(7) 0.0269(7) 0.0037(6) 0.0068(6) 0.0045(6) C13 0.0228(6) 0.0282(7) 0.0284(7) 0.0020(5) 0.0074(6) -0.0012(5) C14 0.0235(6) 0.0227(6) 0.0217(6) 0.0005(5) 0.0086(5) -0.0003(5) C15 0.0238(6) 0.0194(6) 0.0241(6) 0.0004(5) 0.0084(6) -0.0010(5) _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 O1 N1 1.2892(13) . ? O2 N2 1.2816(13) . ? N1 C1 1.3449(16) . ? N1 C2 1.5014(16) . ? N2 C1 1.3563(15) . ? N2 C5 1.5005(15) . ? N3 C11 1.3701(17) . ? N3 C12 1.3768(17) . ? N3 H3N 0.899(18) . ? C1 C8 1.4620(17) . ? C2 C3 1.5268(18) . ? C2 C4 1.5294(19) . ? C2 C5 1.5595(17) . ? C3 H3A 0.995(18) . ? C3 H3B 1.019(19) . ? C3 H3C 0.996(19) . ? C4 H4A 0.979(19) . ? C4 H4B 0.987(18) . ? C4 H4C 0.989(19) . ? C5 C7 1.5211(17) . ? C5 C6 1.5311(17) . ? C6 H6A 1.009(17) . ? C6 H6B 0.982(18) . ? C6 H6C 1.004(17) . ? C7 H7A 0.972(16) . ? C7 H7B 0.997(18) . ? C7 H7C 0.975(18) . ? C8 C15 1.3897(18) . ? C8 C9 1.4213(17) . ? C9 C10 1.3766(18) . ? C9 H9 0.989(15) . ? C10 C11 1.3968(18) . ? C10 H10 0.994(16) . ? C11 C14 1.4170(17) . ? C12 C13 1.3621(19) . ? C12 H12 0.993(17) . ? C13 C14 1.4309(19) . ? C13 H13 0.993(17) . ? C14 C15 1.3984(18) . ? C15 H15 0.972(15) . ? 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 O1 N1 C1 126.99(10) . . ? O1 N1 C2 119.75(10) . . ? C1 N1 C2 113.10(10) . . ? O2 N2 C1 126.40(10) . . ? O2 N2 C5 120.57(9) . . ? C1 N2 C5 112.70(10) . . ? C11 N3 C12 108.84(11) . . ? C11 N3 H3N 125.6(11) . . ? C12 N3 H3N 124.7(11) . . ? N1 C1 N2 107.99(11) . . ? N1 C1 C8 126.43(11) . . ? N2 C1 C8 125.46(11) . . ? N1 C2 C3 109.47(10) . . ? N1 C2 C4 106.34(11) . . ? C3 C2 C4 110.28(12) . . ? N1 C2 C5 100.80(9) . . ? C3 C2 C5 114.97(11) . . ? C4 C2 C5 114.14(11) . . ? C2 C3 H3A 107.9(10) . . ? C2 C3 H3B 112.3(10) . . ? H3A C3 H3B 107.8(14) . . ? C2 C3 H3C 106.8(11) . . ? H3A C3 H3C 109.2(15) . . ? H3B C3 H3C 112.8(14) . . ? C2 C4 H4A 110.9(10) . . ? C2 C4 H4B 106.8(10) . . ? H4A C4 H4B 109.4(14) . . ? C2 C4 H4C 111.1(10) . . ? H4A C4 H4C 108.9(14) . . ? H4B C4 H4C 109.6(14) . . ? N2 C5 C7 109.09(10) . . ? N2 C5 C6 106.17(10) . . ? C7 C5 C6 110.23(11) . . ? N2 C5 C2 101.01(9) . . ? C7 C5 C2 115.37(10) . . ? C6 C5 C2 114.07(11) . . ? C5 C6 H6A 111.0(9) . . ? C5 C6 H6B 109.0(10) . . ? H6A C6 H6B 111.0(13) . . ? C5 C6 H6C 110.0(9) . . ? H6A C6 H6C 108.7(13) . . ? H6B C6 H6C 107.1(13) . . ? C5 C7 H7A 110.7(9) . . ? C5 C7 H7B 108.4(10) . . ? H7A C7 H7B 108.6(13) . . ? C5 C7 H7C 111.7(10) . . ? H7A C7 H7C 107.0(13) . . ? H7B C7 H7C 110.4(14) . . ? C15 C8 C9 120.24(12) . . ? C15 C8 C1 119.46(11) . . ? C9 C8 C1 120.26(11) . . ? C10 C9 C8 121.33(12) . . ? C10 C9 H9 119.8(8) . . ? C8 C9 H9 118.9(8) . . ? C9 C10 C11 117.84(11) . . ? C9 C10 H10 121.2(9) . . ? C11 C10 H10 121.0(9) . . ? N3 C11 C10 130.41(11) . . ? N3 C11 C14 107.56(11) . . ? C10 C11 C14 121.99(12) . . ? C13 C12 N3 110.03(12) . . ? C13 C12 H12 132.1(9) . . ? N3 C12 H12 117.9(9) . . ? C12 C13 C14 106.81(11) . . ? C12 C13 H13 124.2(9) . . ? C14 C13 H13 129.0(9) . . ? C15 C14 C11 119.08(12) . . ? C15 C14 C13 134.13(12) . . ? C11 C14 C13 106.76(11) . . ? C8 C15 C14 119.33(11) . . ? C8 C15 H15 121.0(9) . . ? C14 C15 H15 119.6(9) . . ? 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 O1 N1 C1 N2 176.88(11) . . . . ? C2 N1 C1 N2 -7.69(14) . . . . ? O1 N1 C1 C8 0.7(2) . . . . ? C2 N1 C1 C8 176.14(11) . . . . ? O2 N2 C1 N1 179.55(11) . . . . ? C5 N2 C1 N1 -7.12(13) . . . . ? O2 N2 C1 C8 -4.23(19) . . . . ? C5 N2 C1 C8 169.10(11) . . . . ? O1 N1 C2 C3 -44.67(16) . . . . ? C1 N1 C2 C3 139.54(12) . . . . ? O1 N1 C2 C4 74.46(14) . . . . ? C1 N1 C2 C4 -101.34(12) . . . . ? O1 N1 C2 C5 -166.21(11) . . . . ? C1 N1 C2 C5 17.99(13) . . . . ? O2 N2 C5 C7 -46.65(14) . . . . ? C1 N2 C5 C7 139.59(11) . . . . ? O2 N2 C5 C6 72.13(14) . . . . ? C1 N2 C5 C6 -101.64(12) . . . . ? O2 N2 C5 C2 -168.60(10) . . . . ? C1 N2 C5 C2 17.63(12) . . . . ? N1 C2 C5 N2 -19.51(11) . . . . ? C3 C2 C5 N2 -137.09(11) . . . . ? C4 C2 C5 N2 94.03(12) . . . . ? N1 C2 C5 C7 -136.96(11) . . . . ? C3 C2 C5 C7 105.46(13) . . . . ? C4 C2 C5 C7 -23.42(16) . . . . ? N1 C2 C5 C6 93.92(12) . . . . ? C3 C2 C5 C6 -23.66(15) . . . . ? C4 C2 C5 C6 -152.54(12) . . . . ? N1 C1 C8 C15 145.51(12) . . . . ? N2 C1 C8 C15 -30.01(18) . . . . ? N1 C1 C8 C9 -32.32(18) . . . . ? N2 C1 C8 C9 152.16(12) . . . . ? C15 C8 C9 C10 -3.91(19) . . . . ? C1 C8 C9 C10 173.90(11) . . . . ? C8 C9 C10 C11 1.18(18) . . . . ? C12 N3 C11 C10 -177.93(13) . . . . ? C12 N3 C11 C14 -0.05(13) . . . . ? C9 C10 C11 N3 -179.64(12) . . . . ? C9 C10 C11 C14 2.75(18) . . . . ? C11 N3 C12 C13 0.61(14) . . . . ? N3 C12 C13 C14 -0.89(15) . . . . ? N3 C11 C14 C15 177.94(11) . . . . ? C10 C11 C14 C15 -3.97(18) . . . . ? N3 C11 C14 C13 -0.48(13) . . . . ? C10 C11 C14 C13 177.61(11) . . . . ? C12 C13 C14 C15 -177.24(14) . . . . ? C12 C13 C14 C11 0.84(14) . . . . ? C9 C8 C15 C14 2.64(18) . . . . ? C1 C8 C15 C14 -175.20(11) . . . . ? C11 C14 C15 C8 1.16(18) . . . . ? C13 C14 C15 C8 179.06(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O1 0.899(18) 1.933(18) 2.7833(15) 157.2(16) 4_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.87 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.178 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.031 data_compound1 _database_code_CSD 199928 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 N4 O4 S2' _chemical_formula_weight 478.62 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.949(2) _cell_length_b 8.2983(9) _cell_length_c 12.3808(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.442(2) _cell_angle_gamma 90.00 _cell_volume 2371.7(4) _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 prism _exptl_crystal_colour red _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.90 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.7807 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD area detector diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9565 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 30.52 _reflns_number_total 3609 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SMART (Siemens, 1995)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (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^)+(0.0732P)^2^+1.0764P] 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 3609 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.14065(2) -0.05266(5) 0.77873(4) 0.05401(14) Uani 1 1 d . . . C1 C 0.07199(7) -0.0410(2) 0.69325(15) 0.0498(4) Uani 1 1 d . . . C2 C 0.06783(6) 0.07423(18) 0.61224(13) 0.0434(3) Uani 1 1 d . . . C3 C 0.12175(5) 0.15498(14) 0.62156(10) 0.0305(2) Uani 1 1 d . . . C4 C 0.16506(6) 0.09567(17) 0.70847(11) 0.0394(3) Uani 1 1 d . . . C5 C 0.12858(5) 0.29021(14) 0.55280(9) 0.0287(2) Uani 1 1 d . . . C6 C 0.10467(5) 0.49834(15) 0.41751(10) 0.0336(2) Uani 1 1 d . . . C7 C 0.16862(5) 0.51922(15) 0.48724(10) 0.0328(2) Uani 1 1 d . . . C8 C 0.09510(8) 0.4968(2) 0.29067(12) 0.0494(4) Uani 1 1 d . . . C9 C 0.06203(8) 0.6139(2) 0.44966(18) 0.0536(4) Uani 1 1 d . . . C10 C 0.18317(8) 0.68564(19) 0.53893(15) 0.0493(3) Uani 1 1 d . . . C11 C 0.21358(6) 0.4664(2) 0.42697(13) 0.0438(3) Uani 1 1 d . . . N1 N 0.09114(4) 0.33461(13) 0.45504(8) 0.0326(2) Uani 1 1 d . . . N2 N 0.17216(4) 0.39845(13) 0.57876(8) 0.0317(2) Uani 1 1 d . . . O1 O 0.04531(4) 0.25875(14) 0.40328(9) 0.0504(3) Uani 1 1 d . . . O2 O 0.21581(4) 0.39420(14) 0.66506(8) 0.0464(3) Uani 1 1 d . . . H11A H 0.2068(7) 0.358(2) 0.4001(15) 0.045(4) Uiso 1 1 d . . . H2 H 0.0337(9) 0.096(3) 0.5569(18) 0.064(6) Uiso 1 1 d . . . H11B H 0.2529(9) 0.470(2) 0.4814(17) 0.053(5) Uiso 1 1 d . . . H11C H 0.2132(8) 0.536(2) 0.3699(17) 0.054(5) Uiso 1 1 d . . . H10A H 0.2215(9) 0.688(2) 0.5822(17) 0.058(5) Uiso 1 1 d . . . H9A H 0.0655(8) 0.615(3) 0.5312(19) 0.060(5) Uiso 1 1 d . . . H4 H 0.2038(9) 0.126(3) 0.7321(17) 0.061(5) Uiso 1 1 d . . . H10B H 0.1598(9) 0.715(3) 0.590(2) 0.068(6) Uiso 1 1 d . . . H8A H 0.0985(10) 0.606(3) 0.267(2) 0.080(7) Uiso 1 1 d . . . H9B H 0.0237(10) 0.582(3) 0.4119(18) 0.065(6) Uiso 1 1 d . . . H10C H 0.1763(8) 0.765(3) 0.4793(18) 0.062(6) Uiso 1 1 d . . . H8B H 0.1209(9) 0.425(3) 0.2661(18) 0.063(6) Uiso 1 1 d . . . H9C H 0.0675(10) 0.711(3) 0.426(2) 0.078(7) Uiso 1 1 d . . . H8C H 0.0546(9) 0.470(3) 0.2553(17) 0.060(6) Uiso 1 1 d . . . H1 H 0.0456(10) -0.097(3) 0.704(2) 0.081(7) Uiso 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 S1 0.0632(3) 0.0460(2) 0.0497(2) 0.01548(16) 0.00965(18) -0.00452(17) C1 0.0472(8) 0.0458(8) 0.0578(9) 0.0096(7) 0.0165(7) -0.0126(6) C2 0.0346(6) 0.0433(7) 0.0509(8) 0.0065(6) 0.0089(5) -0.0098(5) C3 0.0314(5) 0.0300(5) 0.0308(5) -0.0016(4) 0.0094(4) -0.0040(4) C4 0.0378(6) 0.0401(6) 0.0384(6) 0.0054(5) 0.0067(5) -0.0030(5) C5 0.0279(5) 0.0319(5) 0.0264(5) -0.0023(4) 0.0070(4) -0.0063(4) C6 0.0346(6) 0.0344(6) 0.0321(5) 0.0030(4) 0.0095(4) -0.0036(4) C7 0.0358(6) 0.0335(5) 0.0307(5) -0.0010(4) 0.0115(4) -0.0093(4) C8 0.0534(8) 0.0616(10) 0.0309(6) 0.0091(6) 0.0075(6) -0.0059(7) C9 0.0450(8) 0.0488(9) 0.0686(11) -0.0003(8) 0.0181(8) 0.0066(7) C10 0.0560(9) 0.0374(7) 0.0552(9) -0.0077(6) 0.0159(7) -0.0162(6) C11 0.0391(7) 0.0552(9) 0.0422(7) 0.0000(6) 0.0195(6) -0.0081(6) N1 0.0295(4) 0.0374(5) 0.0286(5) -0.0009(4) 0.0040(4) -0.0088(4) N2 0.0289(4) 0.0376(5) 0.0273(4) -0.0014(4) 0.0053(4) -0.0098(4) O1 0.0409(5) 0.0596(6) 0.0407(5) 0.0016(4) -0.0064(4) -0.0230(5) O2 0.0360(5) 0.0604(6) 0.0349(5) 0.0019(4) -0.0039(4) -0.0182(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 C4 1.6984(14) . ? S1 C1 1.7049(18) . ? C1 C2 1.370(2) . ? C2 C3 1.4320(17) . ? C3 C4 1.3717(17) . ? C3 C5 1.4439(16) . ? C5 N2 1.3494(14) . ? C5 N1 1.3516(15) . ? C6 N1 1.4991(16) . ? C6 C8 1.5255(19) . ? C6 C9 1.529(2) . ? C6 C7 1.5544(17) . ? C7 N2 1.4981(16) . ? C7 C10 1.5230(19) . ? C7 C11 1.5285(18) . ? N1 O1 1.2794(13) . ? N2 O2 1.2809(13) . ? 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 C4 S1 C1 92.74(7) . . ? C2 C1 S1 111.34(11) . . ? C1 C2 C3 112.30(13) . . ? C4 C3 C2 111.88(11) . . ? C4 C3 C5 124.10(11) . . ? C2 C3 C5 123.87(11) . . ? C3 C4 S1 111.73(10) . . ? N2 C5 N1 108.57(10) . . ? N2 C5 C3 125.36(10) . . ? N1 C5 C3 125.99(10) . . ? N1 C6 C8 109.00(11) . . ? N1 C6 C9 105.86(11) . . ? C8 C6 C9 110.22(13) . . ? N1 C6 C7 101.03(9) . . ? C8 C6 C7 115.38(11) . . ? C9 C6 C7 114.40(12) . . ? N2 C7 C10 109.16(11) . . ? N2 C7 C11 105.79(11) . . ? C10 C7 C11 110.67(12) . . ? N2 C7 C6 101.22(9) . . ? C10 C7 C6 114.57(12) . . ? C11 C7 C6 114.51(11) . . ? O1 N1 C5 126.19(11) . . ? O1 N1 C6 121.21(10) . . ? C5 N1 C6 112.21(9) . . ? O2 N2 C5 126.01(11) . . ? O2 N2 C7 121.24(9) . . ? C5 N2 C7 112.38(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.264 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.060