# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'R. Butler' 'Desmond Cunningham' 'P. McArdle' 'Georgina M. Smyth' _publ_contact_author_name 'Prof R Butler' _publ_contact_author_address ; Chemistry Department National University of Ireland Galway IRELAND ; _publ_contact_author_email 'R.DEBUITLEIR@NUIGALWAY.IE' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; A New Tricyclic Ring and a Nitrogen-Sulfur analogue of the Tri-Pentagon bowl: Cycloaddition Reactions of the unstablised 1,34-thiadiazolium-3methanide 1,3-dipole: Steric Influences on the endo-effect: Substituted Pyrrolo [2,1-b]-1,3,4-thiadiazole systems: Azolium 1,3-dipoles. ; data_gs3 _database_code_CSD 194666 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N3 S' _chemical_formula_weight 305.39 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' '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 12.4385(19) _cell_length_b 6.0956(11) _cell_length_c 20.623(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.514(13) _cell_angle_gamma 90.00 _cell_volume 1526.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9283 _exptl_absorpt_correction_T_max 0.9684 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6229 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 21.22 _reflns_number_total 1642 _reflns_number_gt 1520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0401P)^2^+0.5145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1642 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.83371(4) 0.23860(9) 0.95238(2) 0.0361(2) Uani 1 1 d . . . N3 N 0.72431(14) 0.5918(3) 0.96499(8) 0.0350(5) Uani 1 1 d . . . N4 N 0.67087(13) 0.5030(3) 0.90345(8) 0.0321(5) Uani 1 1 d . . . C7A C 0.69994(17) 0.2699(3) 0.89659(10) 0.0294(5) Uani 1 1 d . . . N9 N 0.62485(17) 0.1232(3) 1.04470(10) 0.0532(6) Uani 1 1 d . . . C2 C 0.80812(17) 0.4800(3) 0.99350(10) 0.0309(5) Uani 1 1 d . . . C5 C 0.54978(18) 0.5184(4) 0.89285(12) 0.0470(6) Uani 1 1 d . . . H5A H 0.5202 0.6040 0.8534 0.061 Uiso 1 1 calc R . . H5B H 0.5292 0.5886 0.9306 0.061 Uiso 1 1 calc R . . C6 C 0.50544(18) 0.2856(4) 0.88475(11) 0.0442(6) Uani 1 1 d . . . H6A H 0.4794 0.2496 0.8382 0.057 Uiso 1 1 calc R . . H6B H 0.4453 0.2671 0.9073 0.057 Uiso 1 1 calc R . . C7 C 0.60345(17) 0.1410(3) 0.91631(9) 0.0336(5) Uani 1 1 d . . . H7 H 0.5963 -0.0060 0.8966 0.044 Uiso 1 1 calc R . . C8 C 0.61645(17) 0.1294(3) 0.98875(12) 0.0368(6) Uani 1 1 d . . . C16 C 0.70683(16) 0.2130(3) 0.82593(9) 0.0298(5) Uani 1 1 d . . . C17 C 0.73627(18) 0.0037(4) 0.81058(11) 0.0401(6) Uani 1 1 d . . . H17 H 0.7488 -0.1040 0.8433 0.052 Uiso 1 1 calc R . . C18 C 0.74721(19) -0.0467(4) 0.74710(11) 0.0444(6) Uani 1 1 d . . . H18 H 0.7679 -0.1875 0.7375 0.058 Uiso 1 1 calc R . . C19 C 0.72774(18) 0.1094(4) 0.69808(11) 0.0428(6) Uani 1 1 d . . . H19 H 0.7352 0.0748 0.6554 0.056 Uiso 1 1 calc R . . C20 C 0.69718(19) 0.3167(4) 0.71247(11) 0.0449(6) Uani 1 1 d . . . H20 H 0.6830 0.4227 0.6793 0.058 Uiso 1 1 calc R . . C21 C 0.68730(18) 0.3688(4) 0.77613(10) 0.0386(6) Uani 1 1 d . . . H21 H 0.6673 0.5103 0.7855 0.050 Uiso 1 1 calc R . . C10 C 0.87867(16) 0.5433(3) 1.05747(9) 0.0325(5) Uani 1 1 d . . . C11 C 0.86729(19) 0.7473(4) 1.08471(11) 0.0414(6) Uani 1 1 d . . . H11 H 0.8166 0.8472 1.0616 0.054 Uiso 1 1 calc R . . C12 C 0.9311(2) 0.8032(4) 1.14620(11) 0.0491(6) Uani 1 1 d . . . H12 H 0.9229 0.9404 1.1643 0.064 Uiso 1 1 calc R . . C13 C 1.00596(19) 0.6573(4) 1.18039(11) 0.0492(7) Uani 1 1 d . . . H13 H 1.0486 0.6953 1.2217 0.064 Uiso 1 1 calc R . . C14 C 1.01807(19) 0.4559(4) 1.15393(12) 0.0511(7) Uani 1 1 d . . . H14 H 1.0689 0.3570 1.1774 0.066 Uiso 1 1 calc R . . C15 C 0.95529(18) 0.3984(4) 1.09259(11) 0.0426(6) Uani 1 1 d . . . H15 H 0.9645 0.2613 1.0748 0.055 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 0.0341(4) 0.0411(4) 0.0314(4) -0.0025(2) 0.0030(3) 0.0044(2) N3 0.0424(11) 0.0299(10) 0.0297(10) -0.0024(8) 0.0011(9) -0.0021(9) N4 0.0346(11) 0.0299(10) 0.0283(10) -0.0009(8) -0.0012(8) 0.0011(8) C7A 0.0336(12) 0.0269(12) 0.0265(12) 0.0022(9) 0.0042(10) -0.0005(9) N9 0.0570(13) 0.0678(15) 0.0377(13) 0.0015(11) 0.0167(10) -0.0054(11) C2 0.0333(13) 0.0310(12) 0.0280(12) 0.0026(10) 0.0058(10) -0.0036(10) C5 0.0375(14) 0.0452(15) 0.0529(15) -0.0021(11) -0.0021(11) 0.0055(11) C6 0.0348(14) 0.0516(15) 0.0424(14) 0.0043(11) -0.0001(11) -0.0052(11) C7 0.0394(13) 0.0332(13) 0.0273(12) -0.0004(9) 0.0053(10) -0.0052(10) C8 0.0341(13) 0.0377(14) 0.0397(15) 0.0019(11) 0.0107(11) -0.0026(10) C16 0.0315(12) 0.0318(13) 0.0246(12) 0.0008(10) 0.0027(9) -0.0041(9) C17 0.0513(15) 0.0370(14) 0.0320(13) 0.0041(10) 0.0087(11) 0.0010(11) C18 0.0536(15) 0.0428(15) 0.0385(14) -0.0078(12) 0.0135(11) 0.0016(11) C19 0.0444(14) 0.0566(17) 0.0275(12) -0.0067(12) 0.0081(10) -0.0070(12) C20 0.0540(15) 0.0501(16) 0.0282(13) 0.0081(11) 0.0037(11) -0.0022(12) C21 0.0492(14) 0.0349(14) 0.0300(13) 0.0023(11) 0.0047(10) 0.0009(11) C10 0.0341(13) 0.0348(14) 0.0273(12) 0.0022(10) 0.0037(10) -0.0073(10) C11 0.0469(14) 0.0404(15) 0.0331(13) 0.0013(11) 0.0002(11) -0.0028(11) C12 0.0592(16) 0.0495(15) 0.0368(14) -0.0086(12) 0.0064(13) -0.0107(13) C13 0.0468(15) 0.0680(19) 0.0287(13) -0.0010(13) -0.0005(11) -0.0160(14) C14 0.0443(15) 0.0629(18) 0.0394(15) 0.0074(13) -0.0059(12) 0.0002(12) C15 0.0423(14) 0.0443(14) 0.0385(14) 0.0007(11) 0.0025(11) -0.0023(11) _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 C2 1.762(2) . ? S1 C7A 1.816(2) . ? N3 C2 1.277(3) . ? N3 N4 1.407(2) . ? N4 C5 1.477(3) . ? N4 C7A 1.480(3) . ? C7A C16 1.518(3) . ? C7A C7 1.560(3) . ? N9 C8 1.136(3) . ? C2 C10 1.469(3) . ? C5 C6 1.519(3) . ? C6 C7 1.530(3) . ? C7 C8 1.469(3) . ? C16 C21 1.381(3) . ? C16 C17 1.383(3) . ? C17 C18 1.380(3) . ? C18 C19 1.371(3) . ? C19 C20 1.370(3) . ? C20 C21 1.382(3) . ? C10 C15 1.383(3) . ? C10 C11 1.384(3) . ? C11 C12 1.385(3) . ? C12 C13 1.368(3) . ? C13 C14 1.365(3) . ? C14 C15 1.380(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 C2 S1 C7A 88.90(10) . . ? C2 N3 N4 112.89(16) . . ? N3 N4 C5 112.10(16) . . ? N3 N4 C7A 112.21(15) . . ? C5 N4 C7A 108.02(16) . . ? N4 C7A C16 112.14(16) . . ? N4 C7A C7 103.93(16) . . ? C16 C7A C7 109.97(16) . . ? N4 C7A S1 104.45(13) . . ? C16 C7A S1 110.46(14) . . ? C7 C7A S1 115.65(13) . . ? N3 C2 C10 122.86(19) . . ? N3 C2 S1 116.02(15) . . ? C10 C2 S1 121.10(16) . . ? N4 C5 C6 106.92(17) . . ? C5 C6 C7 104.74(17) . . ? C8 C7 C6 111.23(17) . . ? C8 C7 C7A 111.58(16) . . ? C6 C7 C7A 100.72(16) . . ? N9 C8 C7 178.7(2) . . ? C21 C16 C17 118.48(19) . . ? C21 C16 C7A 121.28(18) . . ? C17 C16 C7A 120.22(18) . . ? C18 C17 C16 120.5(2) . . ? C19 C18 C17 120.5(2) . . ? C20 C19 C18 119.5(2) . . ? C19 C20 C21 120.2(2) . . ? C16 C21 C20 120.7(2) . . ? C15 C10 C11 118.7(2) . . ? C15 C10 C2 120.8(2) . . ? C11 C10 C2 120.44(19) . . ? C10 C11 C12 120.3(2) . . ? C13 C12 C11 120.2(2) . . ? C14 C13 C12 120.0(2) . . ? C13 C14 C15 120.4(2) . . ? C14 C15 C10 120.4(2) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 21.22 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.307 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.105 data_gs2 _database_code_CSD 194667 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N6 O4 S2' _chemical_formula_weight 546.62 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.537(2) _cell_length_b 11.710(4) _cell_length_c 12.259(2) _cell_angle_alpha 117.58(2) _cell_angle_beta 99.770(10) _cell_angle_gamma 99.90(2) _cell_volume 1265.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8933 _exptl_absorpt_correction_T_max 0.9553 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5814 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 21.21 _reflns_number_total 2577 _reflns_number_gt 2388 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0471P)^2^+0.3996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.043(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2577 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.17392(7) 0.23795(7) 0.73934(7) 0.0604(3) Uani 1 1 d . . . S101 S 0.44452(7) 0.78300(8) 0.69422(7) 0.0647(3) Uani 1 1 d . . . N2 N -0.18959(17) 0.22866(17) 0.60633(18) 0.0364(5) Uani 1 1 d . . . O2 O -0.21279(17) 0.41815(17) 0.60292(18) 0.0551(5) Uani 1 1 d . . . N4 N 0.15612(18) 0.40273(18) 0.65664(18) 0.0386(5) Uani 1 1 d . . . O1 O -0.13384(18) 0.03697(18) 0.5687(2) 0.0677(6) Uani 1 1 d . . . N3 N 0.1280(2) 0.4602(2) 0.77626(19) 0.0475(5) Uani 1 1 d . . . C7A C 0.1321(2) 0.2569(2) 0.6005(2) 0.0421(6) Uani 1 1 d . . . H7A H 0.1945 0.2276 0.5495 0.055 Uiso 1 1 calc R . . N102 N 0.77737(17) 0.69997(17) 0.78274(16) 0.0322(5) Uani 1 1 d . . . O101 O 0.68571(15) 0.67031(16) 0.58466(15) 0.0474(5) Uani 1 1 d . . . O102 O 0.81561(19) 0.67428(19) 0.95867(18) 0.0652(6) Uani 1 1 d . . . N103 N 0.5279(2) 0.8160(2) 0.9204(2) 0.0550(6) Uani 1 1 d . . . N104 N 0.4490(2) 0.6823(2) 0.84236(19) 0.0498(6) Uani 1 1 d . . . C2 C 0.1404(2) 0.3894(3) 0.8277(3) 0.0535(7) Uani 1 1 d . . . H2 H 0.1318 0.4174 0.9098 0.070 Uiso 1 1 calc R . . C5 C 0.0691(2) 0.4212(2) 0.5642(2) 0.0385(6) Uani 1 1 d . . . H5A H 0.1122 0.4207 0.5001 0.050 Uiso 1 1 calc R . . H5B H 0.0481 0.5059 0.6068 0.050 Uiso 1 1 calc R . . C6 C -0.0584(2) 0.3030(2) 0.5019(2) 0.0358(6) Uani 1 1 d . . . H6 H -0.0978 0.2768 0.4124 0.047 Uiso 1 1 calc R . . C7 C -0.0153(2) 0.1884(2) 0.5102(2) 0.0385(6) Uani 1 1 d . . . H7 H -0.0180 0.1171 0.4251 0.050 Uiso 1 1 calc R . . C8 C -0.1154(2) 0.1378(2) 0.5630(2) 0.0415(6) Uani 1 1 d . . . C9 C -0.1612(2) 0.3285(2) 0.5756(2) 0.0360(6) Uani 1 1 d . . . C10 C -0.2868(2) 0.2166(2) 0.6722(2) 0.0398(6) Uani 1 1 d . . . C11 C -0.4208(3) 0.1738(3) 0.6097(3) 0.0534(7) Uani 1 1 d . . . H11 H -0.4489 0.1555 0.5257 0.069 Uiso 1 1 calc R . . C12 C -0.5146(3) 0.1578(3) 0.6717(3) 0.0662(8) Uani 1 1 d . . . H12 H -0.6059 0.1284 0.6294 0.086 Uiso 1 1 calc R . . C13 C -0.4732(3) 0.1850(3) 0.7945(3) 0.0720(9) Uani 1 1 d . . . H13 H -0.5364 0.1727 0.8355 0.094 Uiso 1 1 calc R . . C14 C -0.3404(4) 0.2301(4) 0.8578(3) 0.0835(10) Uani 1 1 d . . . H14 H -0.3131 0.2509 0.9427 0.109 Uiso 1 1 calc R . . C15 C -0.2449(3) 0.2453(3) 0.7965(3) 0.0684(8) Uani 1 1 d . . . H15 H -0.1537 0.2746 0.8393 0.089 Uiso 1 1 calc R . . C102 C 0.5274(3) 0.8762(3) 0.8573(3) 0.0601(8) Uani 1 1 d . . . H102 H 0.5702 0.9677 0.8972 0.078 Uiso 1 1 calc R . . C105 C 0.5046(3) 0.5911(3) 0.8718(3) 0.0548(7) Uani 1 1 d . . . H10A H 0.4339 0.5121 0.8488 0.071 Uiso 1 1 calc R . . H10B H 0.5508 0.6353 0.9626 0.071 Uiso 1 1 calc R . . C106 C 0.6032(2) 0.5520(2) 0.7920(2) 0.0429(6) Uani 1 1 d . . . H106 H 0.6049 0.4596 0.7652 0.056 Uiso 1 1 calc R . . C107 C 0.5535(2) 0.5658(2) 0.6754(2) 0.0393(6) Uani 1 1 d . . . H107 H 0.5184 0.4774 0.5969 0.051 Uiso 1 1 calc R . . C108 C 0.6750(2) 0.6492(2) 0.6703(2) 0.0341(6) Uani 1 1 d . . . C109 C 0.7428(2) 0.6471(2) 0.8577(2) 0.0403(6) Uani 1 1 d . . . C110 C 0.9063(2) 0.7870(2) 0.8112(2) 0.0333(6) Uani 1 1 d . . . C111 C 0.9145(2) 0.9076(2) 0.8150(2) 0.0452(6) Uani 1 1 d . . . H111 H 0.8370 0.9323 0.7997 0.059 Uiso 1 1 calc R . . C112 C 1.0386(3) 0.9908(3) 0.8419(2) 0.0619(8) Uani 1 1 d . . . H112 H 1.0452 1.0725 0.8449 0.081 Uiso 1 1 calc R . . C113 C 1.1528(3) 0.9545(4) 0.8643(3) 0.0704(9) Uani 1 1 d . . . H113 H 1.2365 1.0115 0.8827 0.092 Uiso 1 1 calc R . . C114 C 1.1437(3) 0.8339(3) 0.8597(2) 0.0629(8) Uani 1 1 d . . . H114 H 1.2213 0.8092 0.8745 0.082 Uiso 1 1 calc R . . C115 C 1.0201(2) 0.7493(3) 0.8334(2) 0.0459(6) Uani 1 1 d . . . H115 H 1.0138 0.6678 0.8308 0.060 Uiso 1 1 calc R . . C207 C 0.4391(2) 0.6346(3) 0.7059(2) 0.0486(7) Uani 1 1 d . . . H207 H 0.3518 0.5677 0.6527 0.063 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 0.0581(5) 0.0742(5) 0.0845(6) 0.0638(5) 0.0225(4) 0.0295(4) S101 0.0642(5) 0.0841(6) 0.0635(5) 0.0441(5) 0.0223(4) 0.0381(4) N2 0.0382(11) 0.0348(12) 0.0468(12) 0.0241(10) 0.0222(9) 0.0150(9) O2 0.0607(12) 0.0501(11) 0.0819(13) 0.0433(11) 0.0378(10) 0.0331(9) N4 0.0404(11) 0.0426(12) 0.0441(12) 0.0298(11) 0.0131(9) 0.0137(9) O1 0.0671(13) 0.0453(11) 0.1214(18) 0.0539(12) 0.0525(12) 0.0276(9) N3 0.0529(13) 0.0516(13) 0.0388(12) 0.0252(12) 0.0089(10) 0.0144(10) C7A 0.0415(15) 0.0448(15) 0.0612(17) 0.0366(14) 0.0257(12) 0.0222(11) N102 0.0338(11) 0.0323(11) 0.0278(11) 0.0148(9) 0.0074(9) 0.0055(9) O101 0.0444(10) 0.0629(12) 0.0343(10) 0.0270(9) 0.0100(8) 0.0078(8) O102 0.0704(13) 0.0721(13) 0.0502(12) 0.0424(10) -0.0009(10) -0.0022(10) N103 0.0639(15) 0.0477(14) 0.0458(13) 0.0168(13) 0.0209(11) 0.0137(11) N104 0.0480(13) 0.0516(14) 0.0481(13) 0.0227(12) 0.0231(10) 0.0086(11) C2 0.0512(17) 0.0702(19) 0.0511(16) 0.0415(16) 0.0115(12) 0.0168(13) C5 0.0454(14) 0.0417(14) 0.0417(14) 0.0292(12) 0.0169(11) 0.0150(11) C6 0.0421(14) 0.0394(14) 0.0319(13) 0.0208(12) 0.0133(10) 0.0148(11) C7 0.0458(15) 0.0325(13) 0.0430(14) 0.0184(12) 0.0222(12) 0.0174(11) C8 0.0408(14) 0.0320(14) 0.0570(16) 0.0238(13) 0.0194(12) 0.0134(11) C9 0.0379(14) 0.0354(14) 0.0375(14) 0.0198(12) 0.0103(11) 0.0133(11) C10 0.0424(16) 0.0371(14) 0.0479(16) 0.0240(13) 0.0214(13) 0.0148(11) C11 0.0476(18) 0.0577(17) 0.0513(16) 0.0240(15) 0.0204(14) 0.0117(13) C12 0.0494(17) 0.067(2) 0.073(2) 0.0249(17) 0.0312(16) 0.0118(14) C13 0.076(2) 0.075(2) 0.080(2) 0.0415(19) 0.052(2) 0.0234(17) C14 0.090(3) 0.124(3) 0.064(2) 0.061(2) 0.040(2) 0.039(2) C15 0.0549(18) 0.101(2) 0.061(2) 0.0482(18) 0.0233(15) 0.0226(16) C102 0.0643(19) 0.0507(18) 0.0650(19) 0.0250(17) 0.0270(15) 0.0205(14) C105 0.0614(17) 0.0539(17) 0.0506(16) 0.0280(15) 0.0261(13) 0.0059(13) C106 0.0524(16) 0.0319(13) 0.0403(14) 0.0167(12) 0.0162(12) 0.0041(11) C107 0.0394(14) 0.0347(14) 0.0303(13) 0.0086(11) 0.0104(10) 0.0022(11) C108 0.0371(14) 0.0344(13) 0.0269(13) 0.0117(12) 0.0111(11) 0.0104(10) C109 0.0513(16) 0.0353(14) 0.0329(14) 0.0181(12) 0.0101(13) 0.0081(11) C110 0.0344(14) 0.0342(14) 0.0248(12) 0.0121(11) 0.0072(10) 0.0047(11) C111 0.0491(16) 0.0406(15) 0.0414(15) 0.0202(13) 0.0119(12) 0.0057(12) C112 0.076(2) 0.0479(17) 0.0459(17) 0.0219(15) 0.0125(15) -0.0092(16) C113 0.051(2) 0.085(2) 0.0440(17) 0.0246(17) 0.0045(14) -0.0201(17) C114 0.0370(17) 0.094(2) 0.0451(16) 0.0289(17) 0.0080(12) 0.0103(16) C115 0.0445(17) 0.0516(16) 0.0375(14) 0.0190(13) 0.0116(11) 0.0152(13) C207 0.0342(14) 0.0582(17) 0.0377(15) 0.0165(13) 0.0086(11) 0.0020(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.735(3) . ? S1 C7A 1.808(2) . ? S101 C102 1.735(3) . ? S101 C207 1.801(3) . ? N2 C9 1.387(3) . ? N2 C8 1.389(3) . ? N2 C10 1.435(3) . ? O2 C9 1.201(3) . ? N4 N3 1.412(3) . ? N4 C5 1.454(3) . ? N4 C7A 1.469(3) . ? O1 C8 1.200(3) . ? N3 C2 1.262(3) . ? C7A C7 1.564(3) . ? N102 C109 1.386(3) . ? N102 C108 1.390(3) . ? N102 C110 1.429(3) . ? O101 C108 1.203(3) . ? O102 C109 1.205(3) . ? N103 C102 1.265(3) . ? N103 N104 1.397(3) . ? N104 C105 1.454(3) . ? N104 C207 1.475(3) . ? C5 C6 1.529(3) . ? C6 C9 1.508(3) . ? C6 C7 1.528(3) . ? C7 C8 1.502(3) . ? C10 C11 1.366(3) . ? C10 C15 1.370(4) . ? C11 C12 1.383(4) . ? C12 C13 1.358(4) . ? C13 C14 1.355(4) . ? C14 C15 1.388(4) . ? C105 C106 1.529(4) . ? C106 C109 1.502(3) . ? C106 C107 1.526(3) . ? C107 C108 1.500(3) . ? C107 C207 1.565(3) . ? C110 C115 1.375(3) . ? C110 C111 1.377(3) . ? C111 C112 1.374(4) . ? C112 C113 1.370(4) . ? C113 C114 1.373(4) . ? C114 C115 1.378(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C7A 87.81(12) . . ? C102 S101 C207 87.31(13) . . ? C9 N2 C8 112.39(18) . . ? C9 N2 C10 124.60(19) . . ? C8 N2 C10 122.99(18) . . ? N3 N4 C5 111.47(17) . . ? N3 N4 C7A 110.85(16) . . ? C5 N4 C7A 106.30(17) . . ? C2 N3 N4 110.9(2) . . ? N4 C7A C7 107.07(17) . . ? N4 C7A S1 103.40(15) . . ? C7 C7A S1 118.30(15) . . ? C109 N102 C108 111.82(18) . . ? C109 N102 C110 124.48(18) . . ? C108 N102 C110 123.50(17) . . ? C102 N103 N104 110.5(2) . . ? N103 N104 C105 112.6(2) . . ? N103 N104 C207 111.11(19) . . ? C105 N104 C207 106.0(2) . . ? N3 C2 S1 117.5(2) . . ? N4 C5 C6 105.73(17) . . ? C9 C6 C7 104.52(17) . . ? C9 C6 C5 113.4(2) . . ? C7 C6 C5 105.88(18) . . ? C8 C7 C6 104.73(18) . . ? C8 C7 C7A 115.22(19) . . ? C6 C7 C7A 103.93(17) . . ? O1 C8 N2 123.0(2) . . ? O1 C8 C7 128.6(2) . . ? N2 C8 C7 108.42(18) . . ? O2 C9 N2 124.6(2) . . ? O2 C9 C6 126.9(2) . . ? N2 C9 C6 108.53(19) . . ? C11 C10 C15 120.3(2) . . ? C11 C10 N2 119.8(2) . . ? C15 C10 N2 119.9(2) . . ? C10 C11 C12 119.8(3) . . ? C13 C12 C11 119.9(3) . . ? C14 C13 C12 120.5(3) . . ? C13 C14 C15 120.4(3) . . ? C10 C15 C14 119.1(3) . . ? N103 C102 S101 118.0(2) . . ? N104 C105 C106 105.86(19) . . ? C109 C106 C107 104.56(18) . . ? C109 C106 C105 113.7(2) . . ? C107 C106 C105 106.1(2) . . ? C108 C107 C106 104.83(18) . . ? C108 C107 C207 115.05(19) . . ? C106 C107 C207 103.99(18) . . ? O101 C108 N102 124.2(2) . . ? O101 C108 C107 127.2(2) . . ? N102 C108 C107 108.68(18) . . ? O102 C109 N102 124.2(2) . . ? O102 C109 C106 126.7(2) . . ? N102 C109 C106 109.1(2) . . ? C115 C110 C111 121.0(2) . . ? C115 C110 N102 119.8(2) . . ? C111 C110 N102 119.2(2) . . ? C112 C111 C110 119.1(2) . . ? C113 C112 C111 120.5(3) . . ? C112 C113 C114 120.0(3) . . ? C113 C114 C115 120.3(3) . . ? C110 C115 C114 119.1(3) . . ? N104 C207 C107 106.78(19) . . ? N104 C207 S101 103.52(17) . . ? C107 C207 S101 118.61(16) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 21.21 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.229 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.083 data_gs1 _database_code_CSD 169186 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 N3 O2 S' _chemical_formula_weight 363.43 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' 'O' 'O' 0.0106 0.0060 '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' '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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z' '-x, -y, -z' '-x-1/2, y-1/2, -z' _cell_length_a 12.524(2) _cell_length_b 11.088(3) _cell_length_c 12.935(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.75(2) _cell_angle_gamma 90.00 _cell_volume 1770.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 '4-circle diffractometer' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2370 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.1239 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 21.98 _reflns_number_total 2164 _reflns_number_gt 1072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4 software' _computing_cell_refinement 'Nonius CAD4 software' _computing_data_reduction 'XCAD (P.McArdle, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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=3D1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=3D(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 2164 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1254 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 0.877 _refine_ls_restrained_S_all 0.877 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.07701(9) 0.02494(10) 0.17684(9) 0.0440(4) Uani 1 1 d . . . O1 O -0.0623(2) -0.0080(3) 0.3710(2) 0.0592(9) Uani 1 1 d . . . O2 O 0.2418(3) -0.2334(3) 0.4570(2) 0.0683(11) Uani 1 1 d . . . N2 N 0.0768(3) -0.1441(3) 0.4041(3) 0.0438(10) Uani 1 1 d . . . N4 N 0.2695(3) 0.0415(3) 0.2934(3) 0.0383(9) Uani 1 1 d . . . N3 N 0.2678(3) -0.0676(3) 0.2376(3) 0.0392(9) Uani 1 1 d . . . C7A C 0.1587(3) 0.0938(4) 0.2930(3) 0.0352(11) Uani 1 1 d . . . C2 C 0.1788(4) -0.0848(4) 0.1744(3) 0.0379(11) Uani 1 1 d . . . C5 C 0.3174(3) 0.0225(4) 0.4040(3) 0.0443(12) Uani 1 1 d . . . H5A H 0.3513 0.0958 0.4345 0.058 Uiso 1 1 calc R . . H5B H 0.3714 -0.0411 0.4106 0.058 Uiso 1 1 calc R . . C6 C 0.2230(3) -0.0133(4) 0.4574(3) 0.0402(12) Uani 1 1 d . . . H6 H 0.2378 0.0067 0.5323 0.052 Uiso 1 1 calc R . . C7 C 0.1263(3) 0.0577(4) 0.4010(3) 0.0378(12) Uani 1 1 d . . . H7 H 0.1122 0.1291 0.4412 0.049 Uiso 1 1 calc R . . C8 C 0.0338(4) -0.0293(4) 0.3902(3) 0.0418(11) Uani 1 1 d . . . C9 C 0.1877(4) -0.1430(5) 0.4407(3) 0.0449(12) Uani 1 1 d . . . C10 C 0.0120(4) -0.2534(4) 0.3836(4) 0.0697(15) Uani 1 1 d . . . H10A H 0.0581 -0.3197 0.3727 0.098 Uiso 1 1 calc R . . H10B H -0.0418 -0.2421 0.3220 0.098 Uiso 1 1 calc R . . H10C H -0.0230 -0.2704 0.4425 0.098 Uiso 1 1 calc R . . C11 C 0.1614(4) -0.1877(4) 0.1023(3) 0.0403(12) Uani 1 1 d . . . C12 C 0.0593(4) -0.2180(4) 0.0523(4) 0.0554(14) Uani 1 1 d . . . H12 H 0.0004 -0.1711 0.0625 0.072 Uiso 1 1 calc R . . C13 C 0.0431(4) -0.3174(5) -0.0133(4) 0.0685(16) Uani 1 1 d . . . H13 H -0.0265 -0.3380 -0.0457 0.089 Uiso 1 1 calc R . . C14 C 0.1293(5) -0.3851(5) -0.0304(4) 0.0678(16) Uani 1 1 d . . . H14 H 0.1189 -0.4512 -0.0751 0.088 Uiso 1 1 calc R . . C15 C 0.2317(5) -0.3548(5) 0.0190(4) 0.0664(15) Uani 1 1 d . . . H15 H 0.2903 -0.4014 0.0076 0.086 Uiso 1 1 calc R . . C16 C 0.2492(4) -0.2565(4) 0.0851(4) 0.0592(14) Uani 1 1 d . . . H16 H 0.3190 -0.2366 0.1177 0.077 Uiso 1 1 calc R . . C17 C 0.1568(3) 0.2304(4) 0.2777(3) 0.0364(11) Uani 1 1 d . . . C18 C 0.2397(4) 0.2886(4) 0.2392(3) 0.0493(13) Uani 1 1 d . . . H18 H 0.2991 0.2448 0.2256 0.064 Uiso 1 1 calc R . . C19 C 0.2345(4) 0.4113(4) 0.2211(4) 0.0559(14) Uani 1 1 d . . . H19 H 0.2910 0.4505 0.1968 0.073 Uiso 1 1 calc R . . C20 C 0.1463(5) 0.4749(4) 0.2390(4) 0.0605(14) Uani 1 1 d . . . H20 H 0.1431 0.5575 0.2266 0.079 Uiso 1 1 calc R . . C21 C 0.0615(4) 0.4184(5) 0.2754(4) 0.0584(14) Uani 1 1 d . . . H21 H 0.0012 0.4622 0.2868 0.076 Uiso 1 1 calc R . . C22 C 0.0679(3) 0.2955(4) 0.2945(3) 0.0476(13) Uani 1 1 d . . . H22 H 0.0113 0.2565 0.3189 0.062 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 0.0394(7) 0.0459(7) 0.0460(8) -0.0035(7) 0.0055(5) 0.0036(7) O1 0.0349(19) 0.080(3) 0.064(2) 0.0150(18) 0.0114(16) 0.003(2) O2 0.068(2) 0.054(2) 0.082(3) 0.018(2) 0.010(2) 0.019(2) N2 0.044(3) 0.038(3) 0.050(2) 0.001(2) 0.0095(19) -0.006(2) N4 0.036(2) 0.036(2) 0.044(2) -0.002(2) 0.0097(18) 0.0003(18) N3 0.047(3) 0.035(2) 0.038(2) -0.0022(19) 0.0129(19) 0.0028(19) C7A 0.027(3) 0.035(3) 0.044(3) -0.008(2) 0.008(2) 0.002(2) C2 0.040(3) 0.039(3) 0.036(3) 0.002(2) 0.009(2) 0.002(2) C5 0.037(3) 0.047(3) 0.048(3) -0.012(3) 0.003(2) -0.001(2) C6 0.037(3) 0.043(3) 0.038(3) -0.003(2) 0.000(2) 0.000(2) C7 0.037(3) 0.038(3) 0.040(3) 0.000(2) 0.009(2) 0.002(2) C8 0.043(3) 0.046(3) 0.037(3) 0.005(2) 0.011(2) 0.002(3) C9 0.048(3) 0.050(4) 0.038(3) 0.013(3) 0.012(2) 0.005(3) C10 0.072(4) 0.050(3) 0.088(4) -0.003(3) 0.016(3) -0.023(3) C11 0.049(3) 0.041(3) 0.033(3) -0.003(2) 0.012(2) 0.000(3) C12 0.057(4) 0.052(4) 0.056(3) -0.013(3) 0.004(3) 0.006(3) C13 0.072(4) 0.065(4) 0.064(4) -0.017(3) -0.001(3) -0.005(3) C14 0.096(5) 0.057(4) 0.051(3) -0.018(3) 0.015(3) 0.002(4) C15 0.072(4) 0.064(4) 0.066(4) -0.017(3) 0.021(3) 0.006(3) C16 0.058(3) 0.058(3) 0.063(3) -0.026(3) 0.015(3) -0.004(3) C17 0.034(3) 0.040(3) 0.035(3) -0.005(2) 0.006(2) -0.003(3) C18 0.044(3) 0.044(3) 0.061(3) 0.007(3) 0.010(3) 0.005(3) C19 0.049(4) 0.046(4) 0.071(4) 0.011(3) 0.003(3) -0.011(3) C20 0.075(4) 0.038(3) 0.064(3) 0.004(3) -0.003(3) -0.001(3) C21 0.068(4) 0.047(4) 0.061(3) -0.002(3) 0.014(3) 0.013(3) C22 0.044(3) 0.044(3) 0.058(3) -0.001(3) 0.018(2) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.766(4) . ? S1 C7A 1.835(4) . ? O1 C8 1.210(4) . ? O2 C9 1.209(5) . ? N2 C8 1.382(5) . ? N2 C9 1.390(5) . ? N2 C10 1.457(5) . ? N4 N3 1.407(4) . ? N4 C5 1.469(5) . ? N4 C7A 1.503(5) . ? N3 C2 1.280(5) . ? C7A C17 1.527(5) . ? C7A C7 1.571(5) . ? C2 C11 1.467(5) . ? C5 C6 1.520(5) . ? C6 C9 1.508(6) . ? C6 C7 1.523(5) . ? C7 C8 1.496(6) . ? C11 C12 1.373(5) . ? C11 C16 1.387(6) . ? C12 C13 1.385(6) . ? C13 C14 1.363(6) . ? C14 C15 1.373(6) . ? C15 C16 1.380(6) . ? C17 C22 1.375(5) . ? C17 C18 1.384(5) . ? C18 C19 1.380(5) . ? C19 C20 1.363(6) . ? C20 C21 1.382(6) . ? C21 C22 1.385(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C7A 89.8(2) . . ? C8 N2 C9 112.4(4) . . ? C8 N2 C10 123.4(4) . . ? C9 N2 C10 124.3(4) . . ? N3 N4 C5 110.1(3) . . ? N3 N4 C7A 113.3(3) . . ? C5 N4 C7A 106.5(3) . . ? C2 N3 N4 113.1(3) . . ? N4 C7A C17 112.2(3) . . ? N4 C7A C7 106.0(3) . . ? C17 C7A C7 111.6(3) . . ? N4 C7A S1 103.2(2) . . ? C17 C7A S1 108.2(3) . . ? C7 C7A S1 115.4(3) . . ? N3 C2 C11 122.8(4) . . ? N3 C2 S1 116.0(3) . . ? C11 C2 S1 121.1(3) . . ? N4 C5 C6 105.0(3) . . ? C9 C6 C5 114.6(4) . . ? C9 C6 C7 103.5(3) . . ? C5 C6 C7 105.3(3) . . ? C8 C7 C6 104.6(3) . . ? C8 C7 C7A 113.2(3) . . ? C6 C7 C7A 104.7(3) . . ? O1 C8 N2 124.0(4) . . ? O1 C8 C7 128.4(4) . . ? N2 C8 C7 107.7(4) . . ? O2 C9 N2 123.4(5) . . ? O2 C9 C6 128.6(4) . . ? N2 C9 C6 108.0(4) . . ? C12 C11 C16 119.4(4) . . ? C12 C11 C2 121.1(4) . . ? C16 C11 C2 119.6(4) . . ? C11 C12 C13 120.7(5) . . ? C14 C13 C12 120.0(5) . . ? C13 C14 C15 119.5(5) . . ? C14 C15 C16 121.3(5) . . ? C15 C16 C11 119.1(5) . . ? C22 C17 C18 119.3(4) . . ? C22 C17 C7A 119.7(4) . . ? C18 C17 C7A 120.8(4) . . ? C19 C18 C17 120.2(4) . . ? C20 C19 C18 119.9(5) . . ? C19 C20 C21 121.0(5) . . ? C20 C21 C22 118.8(5) . . ? C17 C22 C21 120.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.193 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.050