# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/427 data_ali1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N O2 S' _chemical_formula_weight 299.38 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 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.4491(11) _cell_length_b 8.7088(15) _cell_length_c 14.951(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.31(3) _cell_angle_gamma 90.00 _cell_volume 707.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8731 _exptl_absorpt_correction_T_max 0.9550 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4743 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2541 _reflns_number_gt 2416 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.002(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(7) _refine_ls_number_reflns 2541 _refine_ls_number_parameters 259 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.006 _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 C2 C 0.0193(3) 0.9087(2) 0.26036(13) 0.0138(4) Uani 1 1 d . . . H2 H 0.166(4) 0.967(3) 0.2838(16) 0.015(5) Uiso 1 1 d . . . C3 C -0.1653(4) 0.9069(2) 0.33361(13) 0.0119(4) Uani 1 1 d . . . H3 H -0.309(4) 0.860(3) 0.3123(14) 0.009(5) Uiso 1 1 d . . . C4 C -0.0712(4) 0.8140(2) 0.41590(13) 0.0142(4) Uani 1 1 d . . . C7 C -0.2155(4) 0.5792(2) 0.33601(14) 0.0146(4) Uani 1 1 d . . . C8 C -0.4093(4) 0.4774(2) 0.34226(14) 0.0179(4) Uani 1 1 d . . . H8 H -0.479(5) 0.470(3) 0.3978(19) 0.026(6) Uiso 1 1 d . . . C9 C -0.4992(4) 0.3923(2) 0.26926(15) 0.0204(5) Uani 1 1 d . . . H9 H -0.639(4) 0.327(3) 0.2753(17) 0.021(6) Uiso 1 1 d . . . C10 C -0.3916(5) 0.4071(2) 0.18858(15) 0.0254(5) Uani 1 1 d . . . H10 H -0.460(5) 0.347(3) 0.1384(17) 0.022(6) Uiso 1 1 d . . . C11 C -0.1997(5) 0.5076(2) 0.18117(16) 0.0242(5) Uani 1 1 d . . . H11 H -0.122(5) 0.525(3) 0.128(2) 0.033(7) Uiso 1 1 d . . . C12 C -0.1084(4) 0.5958(2) 0.25438(13) 0.0174(4) Uani 1 1 d . . . C13 C -0.0849(4) 0.9760(2) 0.17255(13) 0.0152(4) Uani 1 1 d . . . C14 C -0.3056(4) 0.9239(3) 0.12988(14) 0.0205(4) Uani 1 1 d . . . H14 H -0.401(5) 0.837(3) 0.1567(18) 0.028(7) Uiso 1 1 d . . . C15 C -0.3927(4) 0.9843(3) 0.04850(15) 0.0250(5) Uani 1 1 d . . . H15 H -0.552(5) 0.947(3) 0.0162(18) 0.028(7) Uiso 1 1 d . . . C16 C -0.2620(5) 1.0978(3) 0.00702(15) 0.0298(6) Uani 1 1 d . . . H16 H -0.324(5) 1.147(4) -0.051(2) 0.035(7) Uiso 1 1 d . . . C17 C -0.0431(5) 1.1504(3) 0.04936(17) 0.0298(5) Uani 1 1 d . . . H17 H 0.051(5) 1.222(4) 0.0250(18) 0.031(6) Uiso 1 1 d . . . C18 C 0.0438(4) 1.0909(3) 0.13193(15) 0.0224(5) Uani 1 1 d . . . H18 H 0.195(5) 1.123(3) 0.1612(18) 0.028(7) Uiso 1 1 d . . . C19 C -0.2384(4) 1.0723(2) 0.35622(13) 0.0142(4) Uani 1 1 d . . . H19 H -0.322(4) 1.110(2) 0.3024(14) 0.002(5) Uiso 1 1 d . . . C21 C -0.4122(4) 1.0798(2) 0.43058(15) 0.0194(4) Uani 1 1 d . . . H21A H -0.553(5) 1.014(3) 0.4201(18) 0.024(6) Uiso 1 1 d . . . H21B H -0.332(5) 1.054(3) 0.4865(19) 0.019(6) Uiso 1 1 d . . . H21C H -0.480(5) 1.185(4) 0.4400(19) 0.040(8) Uiso 1 1 d . . . N6 N -0.1267(3) 0.66217(19) 0.41288(12) 0.0173(4) Uani 1 1 d . . . H6N H -0.088(4) 0.614(3) 0.4604(17) 0.012(5) Uiso 1 1 d . . . O5 O 0.0338(3) 0.87224(17) 0.48256(9) 0.0209(4) Uani 1 1 d . . . O20 O -0.0201(3) 1.15929(18) 0.37553(11) 0.0206(3) Uani 1 1 d . . . H20Y H -0.051(5) 1.228(4) 0.4056(18) 0.024(7) Uiso 1 1 d . . . S1 S 0.15036(9) 0.71690(5) 0.24505(3) 0.01981(16) 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 C2 0.0149(9) 0.0114(9) 0.0153(10) -0.0009(7) 0.0016(8) 0.0015(8) C3 0.0148(9) 0.0092(9) 0.0115(9) 0.0006(7) -0.0005(7) -0.0011(8) C4 0.0184(10) 0.0115(9) 0.0128(10) 0.0007(8) 0.0011(8) 0.0015(8) C7 0.0213(10) 0.0077(9) 0.0147(10) 0.0016(8) -0.0001(8) 0.0061(8) C8 0.0257(11) 0.0123(9) 0.0162(10) 0.0021(8) 0.0044(9) 0.0049(8) C9 0.0251(11) 0.0102(9) 0.0253(11) 0.0001(8) -0.0022(9) 0.0039(8) C10 0.0427(13) 0.0137(10) 0.0189(11) -0.0037(8) -0.0042(10) 0.0016(10) C11 0.0418(13) 0.0146(10) 0.0171(11) -0.0017(8) 0.0082(10) 0.0034(10) C12 0.0231(10) 0.0109(9) 0.0182(10) 0.0007(8) 0.0022(8) 0.0042(8) C13 0.0212(10) 0.0121(9) 0.0129(10) -0.0011(8) 0.0057(8) 0.0046(8) C14 0.0246(11) 0.0219(10) 0.0148(10) 0.0004(9) 0.0013(9) 0.0001(9) C15 0.0266(11) 0.0320(12) 0.0163(10) -0.0021(9) 0.0003(9) 0.0073(10) C16 0.0448(14) 0.0301(12) 0.0150(11) 0.0041(10) 0.0045(10) 0.0155(11) C17 0.0448(14) 0.0217(11) 0.0247(12) 0.0095(10) 0.0150(11) 0.0026(11) C18 0.0266(11) 0.0196(11) 0.0216(11) 0.0001(9) 0.0071(9) -0.0028(9) C19 0.0184(9) 0.0111(9) 0.0130(10) -0.0011(8) 0.0011(8) 0.0023(8) C21 0.0202(10) 0.0191(11) 0.0196(11) -0.0031(9) 0.0054(9) 0.0015(9) N6 0.0278(9) 0.0128(8) 0.0104(8) 0.0051(7) -0.0031(7) 0.0017(7) O5 0.0316(8) 0.0157(7) 0.0141(8) 0.0018(6) -0.0067(6) -0.0018(6) O20 0.0240(8) 0.0135(7) 0.0247(8) -0.0073(6) 0.0046(6) -0.0028(6) S1 0.0210(3) 0.0143(2) 0.0251(3) 0.0011(2) 0.00769(19) 0.0058(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 C2 C13 1.509(3) . ? C2 C3 1.542(3) . ? C2 S1 1.8374(19) . ? C2 H2 0.99(2) . ? C3 C4 1.529(3) . ? C3 C19 1.539(3) . ? C3 H3 0.92(2) . ? C4 O5 1.222(2) . ? C4 N6 1.356(3) . ? C7 C8 1.387(3) . ? C7 C12 1.399(3) . ? C7 N6 1.412(3) . ? C8 C9 1.378(3) . ? C8 H8 0.94(3) . ? C9 C10 1.386(3) . ? C9 H9 0.96(3) . ? C10 C11 1.375(4) . ? C10 H10 0.97(3) . ? C11 C12 1.398(3) . ? C11 H11 0.94(3) . ? C12 S1 1.775(2) . ? C13 C18 1.388(3) . ? C13 C14 1.394(3) . ? C14 C15 1.377(3) . ? C14 H14 1.02(3) . ? C15 C16 1.391(4) . ? C15 H15 1.01(3) . ? C16 C17 1.385(4) . ? C16 H16 1.00(3) . ? C17 C18 1.389(3) . ? C17 H17 0.90(3) . ? C18 H18 0.94(3) . ? C19 O20 1.421(3) . ? C19 C21 1.515(3) . ? C19 H19 0.95(2) . ? C21 H21A 0.96(3) . ? C21 H21B 0.94(3) . ? C21 H21C 1.00(3) . ? N6 H6N 0.84(3) . ? O20 H20Y 0.78(3) . ? 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 C13 C2 C3 113.51(16) . . ? C13 C2 S1 111.65(13) . . ? C3 C2 S1 111.07(13) . . ? C13 C2 H2 110.5(14) . . ? C3 C2 H2 107.8(14) . . ? S1 C2 H2 101.6(14) . . ? C4 C3 C19 113.29(16) . . ? C4 C3 C2 112.32(16) . . ? C19 C3 C2 109.86(15) . . ? C4 C3 H3 105.8(14) . . ? C19 C3 H3 105.1(14) . . ? C2 C3 H3 110.2(14) . . ? O5 C4 N6 121.45(18) . . ? O5 C4 C3 123.03(18) . . ? N6 C4 C3 115.37(17) . . ? C8 C7 C12 119.64(18) . . ? C8 C7 N6 119.22(19) . . ? C12 C7 N6 121.13(18) . . ? C9 C8 C7 121.1(2) . . ? C9 C8 H8 121.2(16) . . ? C7 C8 H8 117.7(16) . . ? C8 C9 C10 119.4(2) . . ? C8 C9 H9 118.7(16) . . ? C10 C9 H9 121.8(15) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 H10 122.4(16) . . ? C9 C10 H10 117.3(16) . . ? C10 C11 C12 121.0(2) . . ? C10 C11 H11 124.2(17) . . ? C12 C11 H11 114.8(18) . . ? C11 C12 C7 118.6(2) . . ? C11 C12 S1 120.21(17) . . ? C7 C12 S1 121.07(15) . . ? C18 C13 C14 118.78(19) . . ? C18 C13 C2 119.42(18) . . ? C14 C13 C2 121.80(18) . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 118.6(14) . . ? C13 C14 H14 120.8(14) . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 121.7(15) . . ? C16 C15 H15 117.5(15) . . ? C17 C16 C15 118.9(2) . . ? C17 C16 H16 118.4(16) . . ? C15 C16 H16 122.6(17) . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 122.8(16) . . ? C18 C17 H17 116.7(16) . . ? C13 C18 C17 120.5(2) . . ? C13 C18 H18 117.6(17) . . ? C17 C18 H18 121.8(17) . . ? O20 C19 C21 112.80(17) . . ? O20 C19 C3 108.50(16) . . ? C21 C19 C3 112.83(17) . . ? O20 C19 H19 109.1(13) . . ? C21 C19 H19 108.5(12) . . ? C3 C19 H19 104.7(12) . . ? C19 C21 H21A 113.0(16) . . ? C19 C21 H21B 111.6(16) . . ? H21A C21 H21B 108(2) . . ? C19 C21 H21C 113.7(17) . . ? H21A C21 H21C 105(2) . . ? H21B C21 H21C 104(2) . . ? C4 N6 C7 126.02(18) . . ? C4 N6 H6N 115.0(16) . . ? C7 N6 H6N 118.6(16) . . ? C19 O20 H20Y 108(2) . . ? C12 S1 C2 102.23(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 C13 C2 C3 C4 170.17(17) . . . . ? S1 C2 C3 C4 43.39(19) . . . . ? C13 C2 C3 C19 -62.8(2) . . . . ? S1 C2 C3 C19 170.45(13) . . . . ? C19 C3 C4 O5 -29.5(3) . . . . ? C2 C3 C4 O5 95.8(2) . . . . ? C19 C3 C4 N6 146.19(19) . . . . ? C2 C3 C4 N6 -88.6(2) . . . . ? C12 C7 C8 C9 -0.2(3) . . . . ? N6 C7 C8 C9 -179.01(18) . . . . ? C7 C8 C9 C10 1.0(3) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C10 C11 C12 S1 176.48(18) . . . . ? C8 C7 C12 C11 -0.5(3) . . . . ? N6 C7 C12 C11 178.31(18) . . . . ? C8 C7 C12 S1 -176.57(15) . . . . ? N6 C7 C12 S1 2.2(2) . . . . ? C3 C2 C13 C18 128.79(19) . . . . ? S1 C2 C13 C18 -104.73(19) . . . . ? C3 C2 C13 C14 -52.5(2) . . . . ? S1 C2 C13 C14 74.0(2) . . . . ? C18 C13 C14 C15 0.7(3) . . . . ? C2 C13 C14 C15 -178.09(19) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 -0.6(3) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C14 C13 C18 C17 -1.4(3) . . . . ? C2 C13 C18 C17 177.4(2) . . . . ? C16 C17 C18 C13 1.2(4) . . . . ? C4 C3 C19 O20 74.6(2) . . . . ? C2 C3 C19 O20 -52.0(2) . . . . ? C4 C3 C19 C21 -51.2(2) . . . . ? C2 C3 C19 C21 -177.70(16) . . . . ? O5 C4 N6 C7 -170.56(19) . . . . ? C3 C4 N6 C7 13.7(3) . . . . ? C8 C7 N6 C4 -135.4(2) . . . . ? C12 C7 N6 C4 45.8(3) . . . . ? C11 C12 S1 C2 116.11(17) . . . . ? C7 C12 S1 C2 -67.89(17) . . . . ? C13 C2 S1 C12 -88.21(15) . . . . ? C3 C2 S1 C12 39.59(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.277 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.051 data_ali3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O2 S' _chemical_formula_weight 251.34 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.5736(15) _cell_length_b 12.007(3) _cell_length_c 12.669(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1304.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9107 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8705 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2360 _reflns_number_gt 2183 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.0000P] 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 0.04(6) _refine_ls_number_reflns 2360 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.007 _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 C1 C 0.86541(16) 0.64631(11) 0.53776(12) 0.0211(3) Uani 1 1 d . . . C2 C 1.06798(15) 0.60670(12) 0.67283(12) 0.0216(3) Uani 1 1 d . . . C3 C 1.13751(18) 0.66789(14) 0.75283(14) 0.0307(4) Uani 1 1 d . . . H3 H 1.139(2) 0.7467(16) 0.7461(15) 0.037 Uiso 1 1 d . . . C4 C 1.20270(19) 0.61458(16) 0.83936(15) 0.0350(4) Uani 1 1 d . . . H4 H 1.251(2) 0.6572(16) 0.8936(16) 0.042 Uiso 1 1 d . . . C5 C 1.19754(18) 0.49975(15) 0.84752(14) 0.0327(4) Uani 1 1 d . . . H5 H 1.247(2) 0.4644(16) 0.9051(16) 0.039 Uiso 1 1 d . . . C6 C 1.12738(17) 0.43746(13) 0.76796(13) 0.0257(3) Uani 1 1 d . . . H6 H 1.130(2) 0.3589(15) 0.7739(14) 0.031 Uiso 1 1 d . . . C7 C 1.06447(15) 0.48984(12) 0.67879(12) 0.0204(3) Uani 1 1 d . . . C8 C 0.80290(15) 0.44171(12) 0.54366(11) 0.0202(3) Uani 1 1 d . . . H8 H 0.7415(18) 0.3816(13) 0.5808(13) 0.024 Uiso 1 1 d . . . C9 C 0.76208(15) 0.55740(11) 0.58770(12) 0.0184(3) Uani 1 1 d . . . H9 H 0.7805(18) 0.5559(13) 0.6616(14) 0.022 Uiso 1 1 d . . . C10 C 0.58953(14) 0.58835(12) 0.57491(13) 0.0233(3) Uani 1 1 d . . . H10 H 0.5647(19) 0.5988(14) 0.4989(15) 0.028 Uiso 1 1 d . . . C11 C 0.48044(19) 0.50251(15) 0.62225(17) 0.0356(4) Uani 1 1 d . . . H11A H 0.372(2) 0.5331(15) 0.6197(15) 0.043 Uiso 1 1 d . . . H11B H 0.481(2) 0.4341(16) 0.5809(16) 0.043 Uiso 1 1 d . . . H11C H 0.503(2) 0.4868(15) 0.6938(16) 0.043 Uiso 1 1 d . . . C12 C 0.7753(2) 0.42759(13) 0.42479(14) 0.0306(3) Uani 1 1 d . . . H12A H 0.838(2) 0.4796(15) 0.3894(15) 0.037 Uiso 1 1 d . . . H12B H 0.672(2) 0.4409(15) 0.4125(15) 0.037 Uiso 1 1 d . . . C13 C 0.8180(2) 0.31149(15) 0.38484(16) 0.0363(4) Uani 1 1 d . . . H13A H 0.796(2) 0.3012(17) 0.3103(17) 0.044 Uiso 1 1 d . . . H13B H 0.929(2) 0.2986(16) 0.3927(15) 0.044 Uiso 1 1 d . . . H13C H 0.758(2) 0.2526(16) 0.4242(16) 0.044 Uiso 1 1 d . . . N1 N 1.00689(15) 0.66361(9) 0.58296(10) 0.0240(3) Uani 1 1 d . . . H1N H 1.065(2) 0.7127(15) 0.5589(15) 0.032(5) Uiso 1 1 d . . . O1 O 0.82232(12) 0.70014(9) 0.45967(9) 0.0295(3) Uani 1 1 d . . . O2 O 0.57561(15) 0.69306(10) 0.62814(11) 0.0353(3) Uani 1 1 d . . . H2O H 0.492(3) 0.7216(18) 0.6126(17) 0.056(6) Uiso 1 1 d . . . S1 S 1.00902(4) 0.40673(3) 0.56951(3) 0.02399(10) 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 0.0183(7) 0.0200(6) 0.0251(9) 0.0003(6) 0.0000(6) 0.0021(6) C2 0.0123(6) 0.0257(7) 0.0267(9) 0.0008(6) 0.0000(6) 0.0027(6) C3 0.0235(8) 0.0295(8) 0.0391(10) -0.0081(7) -0.0038(7) 0.0023(7) C4 0.0254(8) 0.0505(11) 0.0290(10) -0.0111(8) -0.0078(7) 0.0038(8) C5 0.0234(8) 0.0511(11) 0.0235(9) 0.0050(8) -0.0022(6) 0.0062(7) C6 0.0173(6) 0.0318(8) 0.0281(9) 0.0059(7) 0.0023(6) 0.0024(6) C7 0.0126(6) 0.0256(7) 0.0230(9) 0.0001(6) 0.0014(5) 0.0012(5) C8 0.0142(6) 0.0235(7) 0.0228(8) 0.0028(6) 0.0005(5) -0.0017(5) C9 0.0146(6) 0.0222(7) 0.0184(8) 0.0028(6) -0.0008(5) 0.0012(5) C10 0.0148(6) 0.0284(7) 0.0267(9) 0.0016(7) -0.0012(6) 0.0038(6) C11 0.0154(8) 0.0470(10) 0.0445(11) 0.0096(8) 0.0037(8) -0.0004(8) C12 0.0312(8) 0.0355(8) 0.0250(9) -0.0022(8) -0.0030(7) -0.0021(7) C13 0.0446(11) 0.0373(10) 0.0269(10) -0.0073(8) -0.0006(8) -0.0109(8) N1 0.0174(6) 0.0204(5) 0.0341(7) 0.0068(5) -0.0029(6) -0.0041(5) O1 0.0236(5) 0.0311(5) 0.0337(7) 0.0143(5) -0.0050(5) -0.0045(4) O2 0.0241(6) 0.0366(6) 0.0452(8) -0.0065(6) -0.0067(5) 0.0138(5) S1 0.01785(16) 0.02418(16) 0.0299(2) -0.00593(15) -0.00017(17) 0.00412(15) _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 O1 1.2382(18) . ? C1 N1 1.3574(19) . ? C1 C9 1.525(2) . ? C2 C3 1.386(2) . ? C2 C7 1.405(2) . ? C2 N1 1.4274(19) . ? C3 C4 1.387(3) . ? C3 H3 0.950(19) . ? C4 C5 1.383(3) . ? C4 H4 0.95(2) . ? C5 C6 1.392(2) . ? C5 H5 0.95(2) . ? C6 C7 1.401(2) . ? C6 H6 0.947(17) . ? C7 S1 1.7716(16) . ? C8 C12 1.534(2) . ? C8 C9 1.537(2) . ? C8 S1 1.8458(14) . ? C8 H8 1.010(16) . ? C9 C10 1.5339(18) . ? C9 H9 0.949(17) . ? C10 O2 1.4316(19) . ? C10 C11 1.515(2) . ? C10 H10 0.994(18) . ? C11 H11A 1.00(2) . ? C11 H11B 0.97(2) . ? C11 H11C 0.95(2) . ? C12 C13 1.527(2) . ? C12 H12A 0.94(2) . ? C12 H12B 0.916(19) . ? C13 H13A 0.97(2) . ? C13 H13B 0.97(2) . ? C13 H13C 1.01(2) . ? N1 H1N 0.831(19) . ? O2 H2O 0.82(3) . ? 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 C1 N1 121.59(13) . . ? O1 C1 C9 121.58(12) . . ? N1 C1 C9 116.83(13) . . ? C3 C2 C7 119.93(14) . . ? C3 C2 N1 119.16(13) . . ? C7 C2 N1 120.85(13) . . ? C2 C3 C4 120.42(15) . . ? C2 C3 H3 117.9(12) . . ? C4 C3 H3 121.7(12) . . ? C5 C4 C3 120.41(17) . . ? C5 C4 H4 119.7(12) . . ? C3 C4 H4 119.9(12) . . ? C4 C5 C6 119.69(17) . . ? C4 C5 H5 119.4(12) . . ? C6 C5 H5 120.8(12) . . ? C5 C6 C7 120.60(15) . . ? C5 C6 H6 117.8(11) . . ? C7 C6 H6 121.4(11) . . ? C6 C7 C2 118.90(15) . . ? C6 C7 S1 118.72(11) . . ? C2 C7 S1 121.75(12) . . ? C12 C8 C9 114.91(12) . . ? C12 C8 S1 107.25(10) . . ? C9 C8 S1 111.06(9) . . ? C12 C8 H8 107.4(9) . . ? C9 C8 H8 111.0(9) . . ? S1 C8 H8 104.7(9) . . ? C1 C9 C10 110.30(11) . . ? C1 C9 C8 110.47(11) . . ? C10 C9 C8 113.59(12) . . ? C1 C9 H9 109.0(10) . . ? C10 C9 H9 105.6(9) . . ? C8 C9 H9 107.6(10) . . ? O2 C10 C11 111.07(14) . . ? O2 C10 C9 104.09(12) . . ? C11 C10 C9 112.87(13) . . ? O2 C10 H10 109.2(10) . . ? C11 C10 H10 109.7(10) . . ? C9 C10 H10 109.8(9) . . ? C10 C11 H11A 108.1(11) . . ? C10 C11 H11B 111.0(11) . . ? H11A C11 H11B 107.2(15) . . ? C10 C11 H11C 112.7(12) . . ? H11A C11 H11C 107.3(17) . . ? H11B C11 H11C 110.2(16) . . ? C13 C12 C8 112.92(14) . . ? C13 C12 H12A 108.1(11) . . ? C8 C12 H12A 107.9(11) . . ? C13 C12 H12B 109.5(11) . . ? C8 C12 H12B 107.3(12) . . ? H12A C12 H12B 111.0(16) . . ? C12 C13 H13A 113.0(12) . . ? C12 C13 H13B 110.3(12) . . ? H13A C13 H13B 105.9(16) . . ? C12 C13 H13C 110.8(11) . . ? H13A C13 H13C 107.0(17) . . ? H13B C13 H13C 109.7(16) . . ? C1 N1 C2 126.24(13) . . ? C1 N1 H1N 119.5(13) . . ? C2 N1 H1N 114.2(13) . . ? C10 O2 H2O 109.0(15) . . ? C7 S1 C8 105.51(6) . . ? 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 C7 C2 C3 C4 -0.5(2) . . . . ? N1 C2 C3 C4 -177.76(15) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C4 C5 C6 C7 1.2(2) . . . . ? C5 C6 C7 C2 -2.4(2) . . . . ? C5 C6 C7 S1 168.61(12) . . . . ? C3 C2 C7 C6 2.1(2) . . . . ? N1 C2 C7 C6 179.27(13) . . . . ? C3 C2 C7 S1 -168.66(11) . . . . ? N1 C2 C7 S1 8.52(19) . . . . ? O1 C1 C9 C10 -31.63(19) . . . . ? N1 C1 C9 C10 148.39(13) . . . . ? O1 C1 C9 C8 94.78(16) . . . . ? N1 C1 C9 C8 -85.20(15) . . . . ? C12 C8 C9 C1 -62.85(16) . . . . ? S1 C8 C9 C1 59.10(13) . . . . ? C12 C8 C9 C10 61.70(17) . . . . ? S1 C8 C9 C10 -176.35(10) . . . . ? C1 C9 C10 O2 -59.96(16) . . . . ? C8 C9 C10 O2 175.40(12) . . . . ? C1 C9 C10 C11 179.51(14) . . . . ? C8 C9 C10 C11 54.87(19) . . . . ? C9 C8 C12 C13 179.85(14) . . . . ? S1 C8 C12 C13 55.87(16) . . . . ? O1 C1 N1 C2 179.89(14) . . . . ? C9 C1 N1 C2 -0.1(2) . . . . ? C3 C2 N1 C1 -133.59(15) . . . . ? C7 C2 N1 C1 49.2(2) . . . . ? C6 C7 S1 C8 125.06(11) . . . . ? C2 C7 S1 C8 -64.18(13) . . . . ? C12 C8 S1 C7 149.34(10) . . . . ? C9 C8 S1 C7 23.04(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.157 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.035