# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/498 data_fl0001 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N3 O1.50 S' _chemical_formula_weight 272.36 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 C2/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 47.033(2) _cell_length_b 11.2180(7) _cell_length_c 10.5570(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.501(4) _cell_angle_gamma 90.00 _cell_volume 5564.7(5) _cell_formula_units_Z 16 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 20097 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.230 _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 220(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5846 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3532 _reflns_number_gt 2657 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; "Collect" data collection software, Nonius B.V., 1998. ; _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; "Collect" data collection software, Nonius B.V., 1998. ; _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^)+(0.0886P)^2^+46.6802P] 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 3532 _refine_ls_number_parameters 366 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.2368 _refine_ls_wR_factor_gt 0.2214 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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 0.04416(10) 0.6959(5) 0.6868(5) 0.0634(14) Uani 1 1 d D . . H1A H 0.0639(7) 0.671(6) 0.679(8) 0.095 Uiso 1 1 d D . . H1B H 0.0386(14) 0.778(3) 0.711(8) 0.095 Uiso 1 1 d D . . S1_1 S 0.19903(4) 0.75038(17) 0.82849(18) 0.0557(6) Uani 1 1 d . . . O18_1 O 0.29893(8) 0.7251(4) 0.8028(4) 0.0459(11) Uani 1 1 d . . . H18_1 H 0.3096 0.6908 0.8557 0.069 Uiso 1 1 calc R . . N10_1 N 0.15483(12) 0.3270(5) 0.8499(5) 0.0379(13) Uani 1 1 d . . . H100_1 H 0.1703(16) 0.335(6) 0.811(6) 0.054(11) Uiso 1 1 d . . . H200_1 H 0.1518(15) 0.276(7) 0.898(7) 0.054(11) Uiso 1 1 d . . . N11_1 N 0.08479(10) 0.5074(5) 0.7116(4) 0.0441(13) Uani 1 1 d . . . N13_1 N 0.10730(10) 0.3685(4) 0.8520(4) 0.0347(12) Uani 1 1 d . . . C2_1 C 0.17287(14) 0.6508(6) 0.7844(6) 0.0501(17) Uani 1 1 d . . . H2_1 H 0.1550 0.6479 0.8212 0.060 Uiso 1 1 calc R . . C3_1 C 0.18064(12) 0.5763(6) 0.6900(5) 0.0360(14) Uani 1 1 d . . . C4_1 C 0.20881(12) 0.6003(6) 0.6532(5) 0.0386(15) Uani 1 1 d . . . C5_1 C 0.22136(13) 0.6932(6) 0.7196(6) 0.0426(16) Uani 1 1 d . . . C6_1 C 0.25137(13) 0.7392(6) 0.7146(6) 0.0482(17) Uani 1 1 d . . . H6A_1 H 0.2582 0.7272 0.6291 0.058 Uiso 1 1 calc R . . H6B_1 H 0.2516 0.8250 0.7321 0.058 Uiso 1 1 calc R . . C7_1 C 0.27084(13) 0.6774(7) 0.8084(6) 0.0486(17) Uani 1 1 d . . . H7A_1 H 0.2639 0.6880 0.8939 0.058 Uiso 1 1 calc R . . H7B_1 H 0.2711 0.5918 0.7898 0.058 Uiso 1 1 calc R . . C8_1 C 0.22279(14) 0.5332(6) 0.5505(6) 0.0513(18) Uani 1 1 d . . . H8A_1 H 0.2422 0.5609 0.5442 0.077 Uiso 1 1 calc R . . H8B_1 H 0.2124 0.5464 0.4704 0.077 Uiso 1 1 calc R . . H8C_1 H 0.2229 0.4487 0.5702 0.077 Uiso 1 1 calc R . . C9_1 C 0.16177(12) 0.4838(6) 0.6293(5) 0.0395(15) Uani 1 1 d . . . H9A_1 H 0.1572 0.5076 0.5414 0.047 Uiso 1 1 calc R . . H9B_1 H 0.1723 0.4085 0.6270 0.047 Uiso 1 1 calc R . . C12_1 C 0.08497(12) 0.4313(6) 0.8070(5) 0.0367(15) Uani 1 1 d . . . C14_1 C 0.13232(12) 0.3855(5) 0.7978(5) 0.0312(14) Uani 1 1 d . . . C15_1 C 0.13461(12) 0.4627(6) 0.6936(5) 0.0359(15) Uani 1 1 d . . . C16_1 C 0.11006(13) 0.5204(6) 0.6568(5) 0.0419(16) Uani 1 1 d . . . H16_1 H 0.1108 0.5733 0.5880 0.050 Uiso 1 1 calc R . . C17_1 C 0.05749(13) 0.4123(7) 0.8720(6) 0.0521(18) Uani 1 1 d . . . H17A_1 H 0.0588 0.4488 0.9554 0.078 Uiso 1 1 calc R . . H17B_1 H 0.0540 0.3275 0.8806 0.078 Uiso 1 1 calc R . . H17C_1 H 0.0420 0.4484 0.8220 0.078 Uiso 1 1 calc R . . S1_2 S 0.08915(4) 0.74216(17) 1.00486(17) 0.0549(6) Uani 1 1 d . . . N10_2 N 0.09629(12) 0.8189(5) 0.5545(5) 0.0454(14) Uani 1 1 d . . . H100_2 H 0.0994(14) 0.766(6) 0.495(7) 0.054(11) Uiso 1 1 d . . . H200_2 H 0.0817(15) 0.810(6) 0.608(6) 0.054(11) Uiso 1 1 d . . . N11_2 N 0.16254(11) 1.0463(5) 0.6317(5) 0.0445(13) Uani 1 1 d . . . N13_2 N 0.14192(10) 0.8790(4) 0.5253(4) 0.0370(12) Uani 1 1 d . . . C2_2 C 0.10227(14) 0.8311(6) 0.8903(6) 0.0456(16) Uani 1 1 d . . . H2_2 H 0.1206 0.8224 0.8592 0.055 Uiso 1 1 calc R . . C3_2 C 0.08370(13) 0.9150(6) 0.8490(5) 0.0373(15) Uani 1 1 d . . . C4_2 C 0.05779(14) 0.9092(6) 0.9120(6) 0.0468(17) Uani 1 1 d . . . C5_2 C 0.05743(14) 0.8197(6) 0.9996(6) 0.0495(17) Uani 1 1 d D . . O18_2 O 0.01169(17) 0.6496(9) 0.9087(8) 0.069(3) Uani 0.67 1 d PD A 1 H18_2 H 0.0247 0.6685 0.8621 0.103 Uiso 0.67 1 calc PR A 1 C6_2 C 0.0331(5) 0.774(2) 1.0758(15) 0.060(3) Uani 0.67 1 d PD A 1 H6A_2 H 0.0395 0.7705 1.1653 0.072 Uiso 0.67 1 calc PR A 1 H6B_2 H 0.0174 0.8315 1.0685 0.072 Uiso 0.67 1 calc PR A 1 C7_2 C 0.0218(2) 0.6528(9) 1.0366(11) 0.047(3) Uani 0.67 1 d PD A 1 H7A_2 H 0.0370 0.5937 1.0493 0.056 Uiso 0.67 1 calc PR A 1 H7B_2 H 0.0063 0.6308 1.0912 0.056 Uiso 0.67 1 calc PR A 1 O18'_2 O 0.0063(4) 0.7238(19) 0.9167(18) 0.069(3) Uani 0.33 1 d PD A 2 H18'_2 H 0.0203 0.7330 0.8725 0.103 Uiso 0.33 1 calc PR A 2 C6'_2 C 0.0349(9) 0.794(5) 1.094(3) 0.060(3) Uani 0.33 1 d PD A 2 H6'1_2 H 0.0237 0.8665 1.1086 0.072 Uiso 0.33 1 calc PR A 2 H6'2_2 H 0.0440 0.7697 1.1756 0.072 Uiso 0.33 1 calc PR A 2 C7'_2 C 0.0156(4) 0.695(2) 1.042(2) 0.047(3) Uani 0.33 1 d PD A 2 H7'1_2 H 0.0261 0.6197 1.0425 0.056 Uiso 0.33 1 calc PR A 2 H7'2_2 H -0.0008 0.6864 1.0949 0.056 Uiso 0.33 1 calc PR A 2 C8_2 C 0.03382(17) 0.9935(8) 0.8839(8) 0.082(3) Uani 1 1 d . . . H8A_2 H 0.0335 1.0156 0.7950 0.123 Uiso 1 1 calc R A . H8B_2 H 0.0364 1.0643 0.9358 0.123 Uiso 1 1 calc R . . H8C_2 H 0.0160 0.9554 0.9026 0.123 Uiso 1 1 calc R . . C9_2 C 0.08857(13) 1.0042(6) 0.7473(5) 0.0417(15) Uani 1 1 d . . . H9A_2 H 0.0893 1.0838 0.7856 0.050 Uiso 1 1 calc R . . H9B_2 H 0.0722 1.0026 0.6864 0.050 Uiso 1 1 calc R . . C12_2 C 0.16315(13) 0.9556(6) 0.5505(5) 0.0418(16) Uani 1 1 d . . . C14_2 C 0.11772(13) 0.8923(6) 0.5862(5) 0.0370(15) Uani 1 1 d . . . C15_2 C 0.11526(12) 0.9851(5) 0.6766(5) 0.0357(14) Uani 1 1 d . . . C16_2 C 0.13817(14) 1.0571(6) 0.6927(6) 0.0455(17) Uani 1 1 d . . . H16_2 H 0.1370 1.1197 0.7514 0.055 Uiso 1 1 calc R . . C17_2 C 0.19048(14) 0.9343(7) 0.4854(6) 0.0516(18) Uani 1 1 d . . . H17A_2 H 0.2019 1.0063 0.4890 0.077 Uiso 1 1 calc R . . H17B_2 H 0.1863 0.9129 0.3975 0.077 Uiso 1 1 calc R . . H17C_2 H 0.2009 0.8700 0.5276 0.077 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 O1 0.044(3) 0.086(4) 0.061(3) -0.006(3) 0.006(2) 0.002(3) S1_1 0.0458(11) 0.0538(12) 0.0679(12) -0.0142(9) 0.0071(9) -0.0059(9) O18_1 0.034(2) 0.048(3) 0.056(3) 0.004(2) 0.003(2) -0.006(2) N10_1 0.036(3) 0.044(3) 0.035(3) 0.006(3) 0.008(2) 0.006(3) N11_1 0.033(3) 0.066(4) 0.033(3) 0.005(3) 0.004(2) -0.004(3) N13_1 0.037(3) 0.043(3) 0.024(2) -0.002(2) 0.004(2) -0.004(2) C2_1 0.031(3) 0.061(5) 0.058(4) -0.002(4) 0.007(3) 0.002(3) C3_1 0.028(3) 0.045(4) 0.036(3) 0.006(3) 0.006(3) 0.004(3) C4_1 0.036(3) 0.047(4) 0.033(3) 0.009(3) 0.003(3) 0.006(3) C5_1 0.037(3) 0.045(4) 0.045(4) 0.016(3) 0.001(3) 0.000(3) C6_1 0.037(4) 0.051(4) 0.056(4) 0.013(3) 0.000(3) -0.007(3) C7_1 0.037(4) 0.062(5) 0.048(4) 0.006(3) 0.006(3) -0.006(3) C8_1 0.046(4) 0.058(4) 0.052(4) -0.004(3) 0.016(3) -0.009(3) C9_1 0.039(4) 0.049(4) 0.031(3) 0.002(3) 0.004(3) -0.001(3) C12_1 0.035(3) 0.046(4) 0.030(3) -0.002(3) 0.004(3) 0.002(3) C14_1 0.039(4) 0.027(3) 0.028(3) -0.004(3) 0.001(3) 0.001(3) C15_1 0.034(3) 0.046(4) 0.028(3) 0.001(3) -0.001(3) -0.008(3) C16_1 0.041(4) 0.051(4) 0.034(3) 0.008(3) 0.004(3) -0.001(3) C17_1 0.033(4) 0.075(5) 0.049(4) 0.005(4) 0.008(3) 0.000(3) S1_2 0.0584(12) 0.0534(11) 0.0527(10) 0.0116(9) 0.0017(8) 0.0087(9) N10_2 0.042(3) 0.052(4) 0.042(3) -0.010(3) 0.010(3) -0.004(3) N11_2 0.041(3) 0.049(3) 0.044(3) -0.005(3) 0.006(3) -0.006(3) N13_2 0.040(3) 0.040(3) 0.031(3) -0.004(2) 0.005(2) -0.001(3) C2_2 0.041(4) 0.051(4) 0.045(4) 0.001(3) 0.002(3) 0.003(3) C3_2 0.040(3) 0.041(4) 0.031(3) -0.005(3) 0.002(3) 0.002(3) C4_2 0.046(4) 0.054(4) 0.041(4) 0.000(3) 0.008(3) 0.008(3) C5_2 0.059(4) 0.054(4) 0.036(3) -0.001(3) 0.005(3) 0.016(4) O18_2 0.034(4) 0.108(9) 0.064(4) 0.000(6) 0.010(3) 0.016(5) C6_2 0.075(6) 0.067(10) 0.039(6) -0.004(5) 0.022(5) -0.001(5) C7_2 0.033(6) 0.067(9) 0.041(4) 0.006(6) 0.013(4) 0.026(5) O18'_2 0.034(4) 0.108(9) 0.064(4) 0.000(6) 0.010(3) 0.016(5) C6'_2 0.075(6) 0.067(10) 0.039(6) -0.004(5) 0.022(5) -0.001(5) C7'_2 0.033(6) 0.067(9) 0.041(4) 0.006(6) 0.013(4) 0.026(5) C8_2 0.064(5) 0.098(7) 0.088(6) 0.044(5) 0.037(4) 0.041(5) C9_2 0.042(4) 0.048(4) 0.035(3) -0.003(3) 0.006(3) 0.008(3) C12_2 0.039(4) 0.058(4) 0.029(3) -0.002(3) 0.004(3) 0.002(3) C14_2 0.041(4) 0.041(4) 0.029(3) 0.004(3) 0.006(3) 0.005(3) C15_2 0.039(4) 0.038(4) 0.030(3) 0.002(3) 0.004(3) 0.002(3) C16_2 0.054(4) 0.048(4) 0.035(3) -0.013(3) 0.004(3) -0.001(3) C17_2 0.051(4) 0.059(5) 0.046(4) -0.004(3) 0.008(3) -0.008(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 O1 H1A 0.98(2) . ? O1 H1B 0.99(2) . ? S1_1 C2_1 1.711(7) . ? S1_1 C5_1 1.715(7) . ? O18_1 C7_1 1.429(7) . ? O18_1 H18_1 0.8300 . ? N10_1 C14_1 1.343(8) . ? N10_1 H100_1 0.85(7) . ? N10_1 H200_1 0.78(7) . ? N11_1 C12_1 1.320(8) . ? N11_1 C16_1 1.352(8) . ? N13_1 C12_1 1.335(7) . ? N13_1 C14_1 1.345(7) . ? C2_1 C3_1 1.363(9) . ? C2_1 H2_1 0.9400 . ? C3_1 C4_1 1.423(8) . ? C3_1 C9_1 1.492(9) . ? C4_1 C5_1 1.375(9) . ? C4_1 C8_1 1.496(9) . ? C5_1 C6_1 1.506(9) . ? C6_1 C7_1 1.490(9) . ? C6_1 H6A_1 0.9800 . ? C6_1 H6B_1 0.9800 . ? C7_1 H7A_1 0.9800 . ? C7_1 H7B_1 0.9800 . ? C8_1 H8A_1 0.9700 . ? C8_1 H8B_1 0.9700 . ? C8_1 H8C_1 0.9700 . ? C9_1 C15_1 1.491(8) . ? C9_1 H9A_1 0.9800 . ? C9_1 H9B_1 0.9800 . ? C12_1 C17_1 1.505(8) . ? C14_1 C15_1 1.408(8) . ? C15_1 C16_1 1.365(8) . ? C16_1 H16_1 0.9400 . ? C17_1 H17A_1 0.9700 . ? C17_1 H17B_1 0.9700 . ? C17_1 H17C_1 0.9700 . ? S1_2 C2_2 1.704(7) . ? S1_2 C5_2 1.726(7) . ? N10_2 C14_2 1.333(8) . ? N10_2 H100_2 0.88(7) . ? N10_2 H200_2 0.91(7) . ? N11_2 C12_2 1.332(8) . ? N11_2 C16_2 1.344(8) . ? N13_2 C12_2 1.335(8) . ? N13_2 C14_2 1.340(7) . ? C2_2 C3_2 1.343(9) . ? C2_2 H2_2 0.9400 . ? C3_2 C4_2 1.415(9) . ? C3_2 C9_2 1.493(9) . ? C4_2 C5_2 1.366(9) . ? C4_2 C8_2 1.491(10) . ? C5_2 C6'_2 1.51(2) . ? C5_2 C6_2 1.517(13) . ? O18_2 C7_2 1.413(11) . ? O18_2 H18_2 0.8300 . ? C6_2 C7_2 1.511(15) . ? C6_2 H6A_2 0.9800 . ? C6_2 H6B_2 0.9800 . ? C7_2 H7A_2 0.9800 . ? C7_2 H7B_2 0.9800 . ? O18'_2 C7'_2 1.409(18) . ? O18'_2 H18'_2 0.8300 . ? C6'_2 C7'_2 1.523(19) . ? C6'_2 H6'1_2 0.9800 . ? C6'_2 H6'2_2 0.9800 . ? C7'_2 H7'1_2 0.9800 . ? C7'_2 H7'2_2 0.9800 . ? C8_2 H8A_2 0.9700 . ? C8_2 H8B_2 0.9700 . ? C8_2 H8C_2 0.9700 . ? C9_2 C15_2 1.504(8) . ? C9_2 H9A_2 0.9800 . ? C9_2 H9B_2 0.9800 . ? C12_2 C17_2 1.503(9) . ? C14_2 C15_2 1.420(8) . ? C15_2 C16_2 1.352(9) . ? C16_2 H16_2 0.9400 . ? C17_2 H17A_2 0.9700 . ? C17_2 H17B_2 0.9700 . ? C17_2 H17C_2 0.9700 . ? 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 H1A O1 H1B 124(4) . . ? C2_1 S1_1 C5_1 91.6(3) . . ? C7_1 O18_1 H18_1 109.5 . . ? C14_1 N10_1 H100_1 115(5) . . ? C14_1 N10_1 H200_1 117(5) . . ? H100_1 N10_1 H200_1 125(7) . . ? C12_1 N11_1 C16_1 114.8(5) . . ? C12_1 N13_1 C14_1 117.6(5) . . ? C3_1 C2_1 S1_1 112.8(5) . . ? C3_1 C2_1 H2_1 123.6 . . ? S1_1 C2_1 H2_1 123.6 . . ? C2_1 C3_1 C4_1 111.5(6) . . ? C2_1 C3_1 C9_1 124.5(5) . . ? C4_1 C3_1 C9_1 123.9(5) . . ? C5_1 C4_1 C3_1 112.8(6) . . ? C5_1 C4_1 C8_1 124.0(6) . . ? C3_1 C4_1 C8_1 123.2(6) . . ? C4_1 C5_1 C6_1 128.6(6) . . ? C4_1 C5_1 S1_1 111.3(5) . . ? C6_1 C5_1 S1_1 119.8(5) . . ? C7_1 C6_1 C5_1 111.5(5) . . ? C7_1 C6_1 H6A_1 109.3 . . ? C5_1 C6_1 H6A_1 109.3 . . ? C7_1 C6_1 H6B_1 109.3 . . ? C5_1 C6_1 H6B_1 109.3 . . ? H6A_1 C6_1 H6B_1 108.0 . . ? O18_1 C7_1 C6_1 109.9(5) . . ? O18_1 C7_1 H7A_1 109.7 . . ? C6_1 C7_1 H7A_1 109.7 . . ? O18_1 C7_1 H7B_1 109.7 . . ? C6_1 C7_1 H7B_1 109.7 . . ? H7A_1 C7_1 H7B_1 108.2 . . ? C4_1 C8_1 H8A_1 109.5 . . ? C4_1 C8_1 H8B_1 109.5 . . ? H8A_1 C8_1 H8B_1 109.5 . . ? C4_1 C8_1 H8C_1 109.5 . . ? H8A_1 C8_1 H8C_1 109.5 . . ? H8B_1 C8_1 H8C_1 109.5 . . ? C15_1 C9_1 C3_1 114.9(5) . . ? C15_1 C9_1 H9A_1 108.6 . . ? C3_1 C9_1 H9A_1 108.6 . . ? C15_1 C9_1 H9B_1 108.6 . . ? C3_1 C9_1 H9B_1 108.6 . . ? H9A_1 C9_1 H9B_1 107.5 . . ? N11_1 C12_1 N13_1 126.3(5) . . ? N11_1 C12_1 C17_1 117.5(5) . . ? N13_1 C12_1 C17_1 116.2(5) . . ? N10_1 C14_1 N13_1 116.4(5) . . ? N10_1 C14_1 C15_1 122.4(5) . . ? N13_1 C14_1 C15_1 121.2(5) . . ? C16_1 C15_1 C14_1 114.9(5) . . ? C16_1 C15_1 C9_1 121.8(5) . . ? C14_1 C15_1 C9_1 123.3(5) . . ? N11_1 C16_1 C15_1 125.2(6) . . ? N11_1 C16_1 H16_1 117.4 . . ? C15_1 C16_1 H16_1 117.4 . . ? C12_1 C17_1 H17A_1 109.5 . . ? C12_1 C17_1 H17B_1 109.5 . . ? H17A_1 C17_1 H17B_1 109.5 . . ? C12_1 C17_1 H17C_1 109.5 . . ? H17A_1 C17_1 H17C_1 109.5 . . ? H17B_1 C17_1 H17C_1 109.5 . . ? C2_2 S1_2 C5_2 91.2(3) . . ? C14_2 N10_2 H100_2 116(5) . . ? C14_2 N10_2 H200_2 120(4) . . ? H100_2 N10_2 H200_2 121(6) . . ? C12_2 N11_2 C16_2 114.8(5) . . ? C12_2 N13_2 C14_2 118.5(5) . . ? C3_2 C2_2 S1_2 112.9(5) . . ? C3_2 C2_2 H2_2 123.5 . . ? S1_2 C2_2 H2_2 123.5 . . ? C2_2 C3_2 C4_2 112.1(6) . . ? C2_2 C3_2 C9_2 125.8(6) . . ? C4_2 C3_2 C9_2 122.1(5) . . ? C5_2 C4_2 C3_2 112.9(6) . . ? C5_2 C4_2 C8_2 124.7(6) . . ? C3_2 C4_2 C8_2 122.5(6) . . ? C4_2 C5_2 C6'_2 128(3) . . ? C4_2 C5_2 C6_2 129.8(14) . . ? C6'_2 C5_2 C6_2 11.8(15) . . ? C4_2 C5_2 S1_2 110.9(5) . . ? C6'_2 C5_2 S1_2 121(3) . . ? C6_2 C5_2 S1_2 118.9(13) . . ? C7_2 O18_2 H18_2 109.5 . . ? C7_2 C6_2 C5_2 115.0(12) . . ? C7_2 C6_2 H6A_2 108.5 . . ? C5_2 C6_2 H6A_2 108.5 . . ? C7_2 C6_2 H6B_2 108.5 . . ? C5_2 C6_2 H6B_2 108.5 . . ? H6A_2 C6_2 H6B_2 107.5 . . ? O18_2 C7_2 C6_2 112.6(11) . . ? O18_2 C7_2 H7A_2 109.1 . . ? C6_2 C7_2 H7A_2 109.1 . . ? O18_2 C7_2 H7B_2 109.1 . . ? C6_2 C7_2 H7B_2 109.1 . . ? H7A_2 C7_2 H7B_2 107.8 . . ? C7'_2 O18'_2 H18'_2 109.5 . . ? C5_2 C6'_2 C7'_2 108.5(17) . . ? C5_2 C6'_2 H6'1_2 110.0 . . ? C7'_2 C6'_2 H6'1_2 110.0 . . ? C5_2 C6'_2 H6'2_2 110.0 . . ? C7'_2 C6'_2 H6'2_2 110.0 . . ? H6'1_2 C6'_2 H6'2_2 108.4 . . ? O18'_2 C7'_2 C6'_2 109.4(18) . . ? O18'_2 C7'_2 H7'1_2 109.8 . . ? C6'_2 C7'_2 H7'1_2 109.8 . . ? O18'_2 C7'_2 H7'2_2 109.8 . . ? C6'_2 C7'_2 H7'2_2 109.8 . . ? H7'1_2 C7'_2 H7'2_2 108.2 . . ? C4_2 C8_2 H8A_2 109.5 . . ? C4_2 C8_2 H8B_2 109.5 . . ? H8A_2 C8_2 H8B_2 109.5 . . ? C4_2 C8_2 H8C_2 109.5 . . ? H8A_2 C8_2 H8C_2 109.5 . . ? H8B_2 C8_2 H8C_2 109.5 . . ? C3_2 C9_2 C15_2 114.8(5) . . ? C3_2 C9_2 H9A_2 108.6 . . ? C15_2 C9_2 H9A_2 108.6 . . ? C3_2 C9_2 H9B_2 108.6 . . ? C15_2 C9_2 H9B_2 108.6 . . ? H9A_2 C9_2 H9B_2 107.6 . . ? N11_2 C12_2 N13_2 125.7(6) . . ? N11_2 C12_2 C17_2 117.3(6) . . ? N13_2 C12_2 C17_2 117.0(6) . . ? N10_2 C14_2 N13_2 117.4(6) . . ? N10_2 C14_2 C15_2 122.6(6) . . ? N13_2 C14_2 C15_2 120.0(6) . . ? C16_2 C15_2 C14_2 115.8(5) . . ? C16_2 C15_2 C9_2 122.0(6) . . ? C14_2 C15_2 C9_2 122.2(5) . . ? N11_2 C16_2 C15_2 125.3(6) . . ? N11_2 C16_2 H16_2 117.4 . . ? C15_2 C16_2 H16_2 117.4 . . ? C12_2 C17_2 H17A_2 109.5 . . ? C12_2 C17_2 H17B_2 109.5 . . ? H17A_2 C17_2 H17B_2 109.5 . . ? C12_2 C17_2 H17C_2 109.5 . . ? H17A_2 C17_2 H17C_2 109.5 . . ? H17B_2 C17_2 H17C_2 109.5 . . ? 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 C5_1 S1_1 C2_1 C3_1 0.0(5) . . . . ? S1_1 C2_1 C3_1 C4_1 0.5(7) . . . . ? S1_1 C2_1 C3_1 C9_1 -177.5(5) . . . . ? C2_1 C3_1 C4_1 C5_1 -0.8(7) . . . . ? C9_1 C3_1 C4_1 C5_1 177.2(5) . . . . ? C2_1 C3_1 C4_1 C8_1 -179.2(6) . . . . ? C9_1 C3_1 C4_1 C8_1 -1.2(9) . . . . ? C3_1 C4_1 C5_1 C6_1 175.3(6) . . . . ? C8_1 C4_1 C5_1 C6_1 -6.3(10) . . . . ? C3_1 C4_1 C5_1 S1_1 0.7(6) . . . . ? C8_1 C4_1 C5_1 S1_1 179.2(5) . . . . ? C2_1 S1_1 C5_1 C4_1 -0.4(5) . . . . ? C2_1 S1_1 C5_1 C6_1 -175.5(5) . . . . ? C4_1 C5_1 C6_1 C7_1 -89.6(8) . . . . ? S1_1 C5_1 C6_1 C7_1 84.5(7) . . . . ? C5_1 C6_1 C7_1 O18_1 -178.7(5) . . . . ? C2_1 C3_1 C9_1 C15_1 -9.9(9) . . . . ? C4_1 C3_1 C9_1 C15_1 172.3(5) . . . . ? C16_1 N11_1 C12_1 N13_1 0.0(9) . . . . ? C16_1 N11_1 C12_1 C17_1 -179.8(6) . . . . ? C14_1 N13_1 C12_1 N11_1 1.7(9) . . . . ? C14_1 N13_1 C12_1 C17_1 -178.5(5) . . . . ? C12_1 N13_1 C14_1 N10_1 175.9(5) . . . . ? C12_1 N13_1 C14_1 C15_1 -2.8(8) . . . . ? N10_1 C14_1 C15_1 C16_1 -176.4(5) . . . . ? N13_1 C14_1 C15_1 C16_1 2.3(8) . . . . ? N10_1 C14_1 C15_1 C9_1 1.9(9) . . . . ? N13_1 C14_1 C15_1 C9_1 -179.4(5) . . . . ? C3_1 C9_1 C15_1 C16_1 93.8(7) . . . . ? C3_1 C9_1 C15_1 C14_1 -84.4(7) . . . . ? C12_1 N11_1 C16_1 C15_1 -0.6(9) . . . . ? C14_1 C15_1 C16_1 N11_1 -0.5(9) . . . . ? C9_1 C15_1 C16_1 N11_1 -178.9(6) . . . . ? C5_2 S1_2 C2_2 C3_2 -0.4(5) . . . . ? S1_2 C2_2 C3_2 C4_2 0.4(7) . . . . ? S1_2 C2_2 C3_2 C9_2 -178.4(5) . . . . ? C2_2 C3_2 C4_2 C5_2 -0.3(8) . . . . ? C9_2 C3_2 C4_2 C5_2 178.6(6) . . . . ? C2_2 C3_2 C4_2 C8_2 179.5(7) . . . . ? C9_2 C3_2 C4_2 C8_2 -1.6(10) . . . . ? C3_2 C4_2 C5_2 C6'_2 172.9(12) . . . . ? C8_2 C4_2 C5_2 C6'_2 -6.9(16) . . . . ? C3_2 C4_2 C5_2 C6_2 -172.1(8) . . . . ? C8_2 C4_2 C5_2 C6_2 8.1(13) . . . . ? C3_2 C4_2 C5_2 S1_2 0.1(7) . . . . ? C8_2 C4_2 C5_2 S1_2 -179.7(6) . . . . ? C2_2 S1_2 C5_2 C4_2 0.2(5) . . . . ? C2_2 S1_2 C5_2 C6'_2 -173.3(13) . . . . ? C2_2 S1_2 C5_2 C6_2 173.3(7) . . . . ? C4_2 C5_2 C6_2 C7_2 108(2) . . . . ? C6'_2 C5_2 C6_2 C7_2 -166(20) . . . . ? S1_2 C5_2 C6_2 C7_2 -63(2) . . . . ? C5_2 C6_2 C7_2 O18_2 -59(2) . . . . ? C4_2 C5_2 C6'_2 C7'_2 99(4) . . . . ? C6_2 C5_2 C6'_2 C7'_2 -4(15) . . . . ? S1_2 C5_2 C6'_2 C7'_2 -89(3) . . . . ? C5_2 C6'_2 C7'_2 O18'_2 -50(5) . . . . ? C2_2 C3_2 C9_2 C15_2 8.2(9) . . . . ? C4_2 C3_2 C9_2 C15_2 -170.6(6) . . . . ? C16_2 N11_2 C12_2 N13_2 1.1(9) . . . . ? C16_2 N11_2 C12_2 C17_2 -176.3(6) . . . . ? C14_2 N13_2 C12_2 N11_2 -0.3(9) . . . . ? C14_2 N13_2 C12_2 C17_2 177.0(5) . . . . ? C12_2 N13_2 C14_2 N10_2 176.5(5) . . . . ? C12_2 N13_2 C14_2 C15_2 -1.0(8) . . . . ? N10_2 C14_2 C15_2 C16_2 -175.9(6) . . . . ? N13_2 C14_2 C15_2 C16_2 1.5(8) . . . . ? N10_2 C14_2 C15_2 C9_2 2.5(9) . . . . ? N13_2 C14_2 C15_2 C9_2 179.8(5) . . . . ? C3_2 C9_2 C15_2 C16_2 -107.7(7) . . . . ? C3_2 C9_2 C15_2 C14_2 74.0(7) . . . . ? C12_2 N11_2 C16_2 C15_2 -0.5(9) . . . . ? C14_2 C15_2 C16_2 N11_2 -0.7(9) . . . . ? C9_2 C15_2 C16_2 N11_2 -179.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.350 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.077