Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_2CF31_C.FONSECA_/_R.A.W.JO #------------------------------------------------------------------------------ _audit_creation_date '19100-07-16' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 7.141(5) _cell_length_b 6.945(2) _cell_length_c 18.886(5) _cell_angle_alpha 90 _cell_angle_beta 95.13(4) _cell_angle_gamma 90 _cell_volume 932.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 153.2 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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' #------------------------------------------------------------------------------ _exptl_crystal_description 'unknown' _exptl_crystal_colour 'unknown' _exptl_crystal_size_max 0.00 _exptl_crystal_size_mid 0.00 _exptl_crystal_size_min 0.00 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 210.25 _chemical_formula_analytical ? _chemical_formula_sum 'C9 H10 N2 O2 S ' _chemical_formula_moiety 'C9 H10 N2 O2 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 440.00 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.900 _exptl_special_details ; The scan width was (0.00+0.00tan\q)\% with an \w scan speed of 0\% per minute . Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 153.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC6S' _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.22 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 1951 _reflns_number_total 1801 _reflns_number_observed 1063 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.05365 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 100 _diffrn_reflns_limit_h_max -100 _diffrn_reflns_limit_k_min 100 _diffrn_reflns_limit_k_max -100 _diffrn_reflns_limit_l_min 100 _diffrn_reflns_limit_l_max -100 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00978 _diffrn_orient_matrix_UB_12 0.14334 _diffrn_orient_matrix_UB_13 -0.00304 _diffrn_orient_matrix_UB_21 0.01844 _diffrn_orient_matrix_UB_22 0.00779 _diffrn_orient_matrix_UB_23 0.05304 _diffrn_orient_matrix_UB_31 0.13905 _diffrn_orient_matrix_UB_32 -0.01111 _diffrn_orient_matrix_UB_33 -0.00202 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 36 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 40 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S 0 4 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.3195(1) 0.2395(1) 0.40607(4) 0.0217(2) 1.000 . Uani d ? O(1) 0.4051(3) 0.0549(4) 0.3968(1) 0.0323(8) 1.000 . Uani d ? O(2) 0.4461(3) 0.4006(4) 0.4057(1) 0.0296(7) 1.000 . Uani d ? N(1) 0.1392(3) 0.2703(4) 0.3478(1) 0.0227(7) 1.000 . Uani d ? N(2) -0.1839(4) 0.2969(4) 0.3459(1) 0.0246(8) 1.000 . Uani d ? C(1) -0.0165(4) 0.2772(5) 0.3808(2) 0.0190(8) 1.000 . Uani d ? C(2) 0.0054(4) 0.2609(5) 0.4597(2) 0.0183(7) 1.000 . Uani d ? C(3) 0.1951(4) 0.2429(5) 0.4830(2) 0.0190(8) 1.000 . Uani d ? C(4) 0.2593(4) 0.2270(5) 0.5535(2) 0.0247(9) 1.000 . Uani d ? C(5) 0.1251(5) 0.2307(5) 0.6022(2) 0.0268(9) 1.000 . Uani d ? C(6) -0.0645(4) 0.2495(5) 0.5797(2) 0.0264(9) 1.000 . Uani d ? C(7) -0.1271(4) 0.2648(5) 0.5087(2) 0.0224(8) 1.000 . Uani d ? C(8) -0.2154(5) 0.3152(6) 0.2687(2) 0.038(1) 1.000 . Uani d ? C(9) -0.3820(6) 0.2013(6) 0.2404(2) 0.042(1) 1.000 . Uani d ? H(1) -0.2925 0.3002 0.3733 0.025 1.000 . Uiso c ? H(2) 0.3922 0.2129 0.5675 0.031 1.000 . Uiso c ? H(3) 0.1653 0.2207 0.6527 0.033 1.000 . Uiso c ? H(4) -0.1548 0.2512 0.6142 0.030 1.000 . Uiso c ? H(5) -0.2577 0.2786 0.4928 0.027 1.000 . Uiso c ? H(6) -0.2357 0.4479 0.2559 0.042 1.000 . Uiso c ? H(7) -0.1065 0.2713 0.2476 0.042 1.000 . Uiso c ? H(8) -0.4936 0.2441 0.2592 0.049 1.000 . Uiso c ? H(9) -0.4013 0.2115 0.1889 0.049 1.000 . Uiso c ? H(10) -0.3646 0.0671 0.2513 0.049 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0127(4) 0.0275(5) 0.0245(4) 0.0023(4) 0.0033(3) 0.0014(4) O(1) 0.024(1) 0.035(2) 0.037(2) 0.012(1) 0.009(1) -0.003(1) O(2) 0.015(1) 0.039(2) 0.035(2) -0.005(1) 0.003(1) 0.005(1) N(1) 0.014(1) 0.032(2) 0.022(1) 0.000(1) 0.003(1) 0.001(1) N(2) 0.015(1) 0.039(2) 0.020(1) -0.002(1) 0.003(1) 0.002(1) C(1) 0.016(1) 0.017(2) 0.023(2) -0.001(1) 0.002(1) -0.003(1) C(2) 0.017(1) 0.017(2) 0.021(2) -0.001(2) 0.001(1) -0.001(2) C(3) 0.018(1) 0.015(2) 0.024(2) 0.000(2) 0.003(1) -0.002(2) C(4) 0.022(2) 0.024(2) 0.027(2) 0.002(2) -0.005(1) 0.003(2) C(5) 0.036(2) 0.022(2) 0.021(2) -0.004(2) -0.001(1) 0.002(2) C(6) 0.028(2) 0.025(2) 0.026(2) -0.002(2) 0.009(1) -0.001(2) C(7) 0.018(2) 0.024(2) 0.024(2) -0.001(2) 0.002(1) -0.001(2) C(8) 0.024(2) 0.065(3) 0.022(2) -0.004(2) -0.003(2) 0.009(2) C(9) 0.048(2) 0.050(3) 0.026(2) -0.010(2) 0.000(2) -0.006(2) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1063 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0373 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0433 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.526 _refine_ls_shift/esd_max 0.0020 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.29 _refine_diff_density_max 0.25 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag ? ? ? ? ? ? # -- ENTER BONDS HERE, ONE PER LINE -- # e.g. C1 C2 1.541(1) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag # -- ENTER ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 109.4(3) . . . yes ? ? ? ? ? ? ? ? #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? # -- ENTER NON-BONDED CONTACTS HERE, ONE PER LINE -- # e.g. O1 N1 2.841(1) . . yes #------------------------------------------------------------------------------ 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 ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ #===END data_liv8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H13 N3 O4 S2' _chemical_formula_weight 375.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.165(2) _cell_length_b 8.224(3) _cell_length_c 12.933(4) _cell_angle_alpha 98.513(16) _cell_angle_beta 107.370(18) _cell_angle_gamma 100.413(17) _cell_volume 796.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 19.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 3.297 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.513 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 4.3 _diffrn_reflns_number 5823 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 67.48 _reflns_number_total 2803 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0438P)^2^+0.5889P] 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 0.0061(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2803 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.75033(6) 0.73544(6) 0.39810(4) 0.01870(17) Uani 1 1 d . . . S2 S 0.71951(6) 0.97910(5) 0.88827(4) 0.01739(17) Uani 1 1 d . . . O1 O 0.7000(2) 0.58360(19) 0.31372(12) 0.0288(4) Uani 1 1 d . . . O2 O 0.8513(2) 0.88374(19) 0.38136(13) 0.0302(4) Uani 1 1 d . . . O3 O 0.8592(2) 1.12184(17) 0.95382(13) 0.0269(4) Uani 1 1 d . . . O4 O 0.54296(19) 1.00310(18) 0.85439(13) 0.0270(4) Uani 1 1 d . . . N1 N 0.8558(2) 0.6954(2) 0.51941(14) 0.0194(4) Uani 1 1 d . . . N2 N 0.7662(2) 0.90533(19) 0.77546(13) 0.0186(4) Uani 1 1 d . . . N3 N 0.8193(2) 0.66266(19) 0.68668(13) 0.0161(3) Uani 1 1 d . . . C1 C 0.5641(2) 0.7695(2) 0.43220(16) 0.0159(4) Uani 1 1 d . . . C2 C 0.4161(3) 0.8121(2) 0.36775(16) 0.0199(4) Uani 1 1 d . . . H2 H 0.4088 0.8388 0.2978 0.024 Uiso 1 1 calc R . . C3 C 0.2792(3) 0.8138(2) 0.41005(18) 0.0233(5) Uani 1 1 d . . . H3 H 0.1765 0.8452 0.3693 0.028 Uiso 1 1 calc R . . C4 C 0.2901(3) 0.7703(2) 0.51151(18) 0.0225(4) Uani 1 1 d . . . H4 H 0.1924 0.7674 0.5372 0.027 Uiso 1 1 calc R . . C5 C 0.4417(3) 0.7309(2) 0.57600(16) 0.0187(4) Uani 1 1 d . . . H5 H 0.4486 0.7018 0.6453 0.022 Uiso 1 1 calc R . . C6 C 0.5821(2) 0.7352(2) 0.53651(15) 0.0147(4) Uani 1 1 d . . . C7 C 0.7610(2) 0.7002(2) 0.58291(15) 0.0151(4) Uani 1 1 d . . . C8 C 0.7840(2) 0.7519(2) 0.77469(15) 0.0156(4) Uani 1 1 d . . . C9 C 0.7659(2) 0.6788(2) 0.87044(15) 0.0165(4) Uani 1 1 d . . . C10 C 0.7733(3) 0.5198(2) 0.89323(17) 0.0209(4) Uani 1 1 d . . . H10 H 0.7932 0.4351 0.8431 0.025 Uiso 1 1 calc R . . C11 C 0.7508(3) 0.4881(3) 0.99114(18) 0.0259(5) Uani 1 1 d . . . H11 H 0.7577 0.3807 1.0084 0.031 Uiso 1 1 calc R . . C12 C 0.7185(3) 0.6092(3) 1.06458(18) 0.0277(5) Uani 1 1 d . . . H12 H 0.7052 0.5839 1.1314 0.033 Uiso 1 1 calc R . . C13 C 0.7052(3) 0.7673(3) 1.04136(17) 0.0229(4) Uani 1 1 d . . . H13 H 0.6802 0.8504 1.0899 0.027 Uiso 1 1 calc R . . C14 C 0.7301(2) 0.7971(2) 0.94414(16) 0.0177(4) Uani 1 1 d . . . C15 C 0.9889(2) 0.6058(2) 0.71648(16) 0.0181(4) Uani 1 1 d . . . H15A H 0.9991 0.5408 0.6488 0.022 Uiso 1 1 calc R . . H15B H 0.9869 0.5297 0.7689 0.022 Uiso 1 1 calc R . . C16 C 1.1480(3) 0.7540(3) 0.76877(18) 0.0246(5) Uani 1 1 d . . . H16A H 1.1492 0.8307 0.7176 0.037 Uiso 1 1 calc R . . H16B H 1.2562 0.7125 0.7845 0.037 Uiso 1 1 calc R . . H16C H 1.1418 0.8149 0.8381 0.037 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 0.0219(3) 0.0252(3) 0.0154(3) 0.00742(19) 0.0113(2) 0.01032(19) S2 0.0205(3) 0.0167(2) 0.0172(3) 0.00241(18) 0.0075(2) 0.00903(18) O1 0.0434(9) 0.0328(8) 0.0172(7) 0.0051(6) 0.0152(7) 0.0177(7) O2 0.0284(8) 0.0373(8) 0.0337(9) 0.0179(7) 0.0179(7) 0.0084(7) O3 0.0299(8) 0.0181(7) 0.0289(8) -0.0024(6) 0.0078(7) 0.0063(6) O4 0.0247(8) 0.0315(8) 0.0296(8) 0.0076(6) 0.0097(6) 0.0168(6) N1 0.0198(8) 0.0271(8) 0.0168(8) 0.0070(7) 0.0096(7) 0.0112(7) N2 0.0216(8) 0.0188(8) 0.0172(8) 0.0039(6) 0.0075(7) 0.0078(6) N3 0.0179(8) 0.0198(8) 0.0140(8) 0.0053(6) 0.0064(6) 0.0098(6) C1 0.0158(9) 0.0165(8) 0.0165(9) 0.0028(7) 0.0072(7) 0.0039(7) C2 0.0218(10) 0.0191(9) 0.0177(10) 0.0045(7) 0.0040(8) 0.0061(7) C3 0.0184(10) 0.0217(10) 0.0260(11) 0.0038(8) 0.0012(8) 0.0069(8) C4 0.0154(9) 0.0238(10) 0.0291(11) 0.0015(8) 0.0106(8) 0.0044(7) C5 0.0202(9) 0.0181(9) 0.0179(10) 0.0024(7) 0.0075(8) 0.0038(7) C6 0.0161(9) 0.0136(8) 0.0150(9) 0.0016(7) 0.0062(7) 0.0047(7) C7 0.0163(9) 0.0146(8) 0.0158(9) 0.0030(7) 0.0067(7) 0.0055(7) C8 0.0128(8) 0.0191(9) 0.0150(9) 0.0036(7) 0.0038(7) 0.0055(7) C9 0.0156(9) 0.0204(9) 0.0133(9) 0.0025(7) 0.0045(7) 0.0054(7) C10 0.0268(10) 0.0182(9) 0.0198(10) 0.0038(7) 0.0096(8) 0.0080(8) C11 0.0339(12) 0.0241(10) 0.0263(11) 0.0112(8) 0.0138(9) 0.0119(9) C12 0.0374(12) 0.0337(11) 0.0203(10) 0.0110(9) 0.0156(9) 0.0142(9) C13 0.0282(11) 0.0264(10) 0.0180(10) 0.0027(8) 0.0118(9) 0.0107(8) C14 0.0173(9) 0.0192(9) 0.0175(9) 0.0040(7) 0.0056(7) 0.0072(7) C15 0.0189(10) 0.0217(9) 0.0181(9) 0.0059(7) 0.0076(8) 0.0116(8) C16 0.0215(10) 0.0297(10) 0.0222(10) 0.0023(8) 0.0071(8) 0.0081(8) _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 O2 1.4266(16) . ? S1 O1 1.4361(16) . ? S1 N1 1.6615(17) . ? S1 C1 1.762(2) . ? S2 O3 1.4287(15) . ? S2 O4 1.4354(16) . ? S2 N2 1.6720(18) . ? S2 C14 1.761(2) . ? N1 C7 1.287(3) . ? N2 C8 1.295(3) . ? N3 C7 1.385(2) . ? N3 C8 1.394(3) . ? N3 C15 1.501(2) . ? C1 C2 1.384(3) . ? C1 C6 1.389(3) . ? C2 C3 1.385(3) . ? C3 C4 1.392(3) . ? C4 C5 1.394(3) . ? C5 C6 1.384(3) . ? C6 C7 1.503(3) . ? C8 C9 1.488(3) . ? C9 C10 1.390(3) . ? C9 C14 1.391(3) . ? C10 C11 1.387(3) . ? C11 C12 1.388(3) . ? C12 C13 1.393(3) . ? C13 C14 1.382(3) . ? C15 C16 1.513(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 O2 S1 O1 117.62(10) . . ? O2 S1 N1 109.65(9) . . ? O1 S1 N1 108.95(9) . . ? O2 S1 C1 113.24(9) . . ? O1 S1 C1 109.47(9) . . ? N1 S1 C1 95.65(9) . . ? O3 S2 O4 117.69(9) . . ? O3 S2 N2 108.06(9) . . ? O4 S2 N2 108.88(9) . . ? O3 S2 C14 112.47(9) . . ? O4 S2 C14 111.49(9) . . ? N2 S2 C14 95.91(9) . . ? C7 N1 S1 110.22(13) . . ? C8 N2 S2 109.68(14) . . ? C7 N3 C8 119.30(15) . . ? C7 N3 C15 116.85(16) . . ? C8 N3 C15 115.86(15) . . ? C2 C1 C6 123.20(19) . . ? C2 C1 S1 128.50(16) . . ? C6 C1 S1 108.19(14) . . ? C1 C2 C3 116.87(19) . . ? C2 C3 C4 120.90(18) . . ? C3 C4 C5 121.2(2) . . ? C6 C5 C4 118.30(19) . . ? C5 C6 C1 119.32(17) . . ? C5 C6 C7 132.32(18) . . ? C1 C6 C7 108.28(17) . . ? N1 C7 N3 120.26(17) . . ? N1 C7 C6 117.35(17) . . ? N3 C7 C6 122.23(17) . . ? N2 C8 N3 119.94(17) . . ? N2 C8 C9 117.28(18) . . ? N3 C8 C9 122.78(16) . . ? C10 C9 C14 119.02(18) . . ? C10 C9 C8 131.48(18) . . ? C14 C9 C8 109.46(16) . . ? C11 C10 C9 118.23(19) . . ? C10 C11 C12 121.78(19) . . ? C11 C12 C13 120.7(2) . . ? C14 C13 C12 116.58(19) . . ? C13 C14 C9 123.62(18) . . ? C13 C14 S2 128.74(16) . . ? C9 C14 S2 107.63(15) . . ? N3 C15 C16 111.77(15) . . ? 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 O2 S1 N1 C7 119.06(14) . . . . ? O1 S1 N1 C7 -110.93(15) . . . . ? C1 S1 N1 C7 1.91(15) . . . . ? O3 S2 N2 C8 117.90(14) . . . . ? O4 S2 N2 C8 -113.19(14) . . . . ? C14 S2 N2 C8 1.94(15) . . . . ? O2 S1 C1 C2 65.03(19) . . . . ? O1 S1 C1 C2 -68.36(19) . . . . ? N1 S1 C1 C2 179.24(17) . . . . ? O2 S1 C1 C6 -118.90(14) . . . . ? O1 S1 C1 C6 107.72(13) . . . . ? N1 S1 C1 C6 -4.68(14) . . . . ? C6 C1 C2 C3 -2.3(3) . . . . ? S1 C1 C2 C3 173.28(14) . . . . ? C1 C2 C3 C4 -1.6(3) . . . . ? C2 C3 C4 C5 2.9(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C1 -3.4(3) . . . . ? C4 C5 C6 C7 -179.74(17) . . . . ? C2 C1 C6 C5 4.9(3) . . . . ? S1 C1 C6 C5 -171.48(14) . . . . ? C2 C1 C6 C7 -178.01(16) . . . . ? S1 C1 C6 C7 5.65(17) . . . . ? S1 N1 C7 N3 176.95(13) . . . . ? S1 N1 C7 C6 1.3(2) . . . . ? C8 N3 C7 N1 143.62(18) . . . . ? C15 N3 C7 N1 -4.0(2) . . . . ? C8 N3 C7 C6 -41.0(2) . . . . ? C15 N3 C7 C6 171.41(15) . . . . ? C5 C6 C7 N1 171.77(19) . . . . ? C1 C6 C7 N1 -4.9(2) . . . . ? C5 C6 C7 N3 -3.8(3) . . . . ? C1 C6 C7 N3 179.60(15) . . . . ? S2 N2 C8 N3 178.50(13) . . . . ? S2 N2 C8 C9 -1.8(2) . . . . ? C7 N3 C8 N2 -28.3(3) . . . . ? C15 N3 C8 N2 119.70(18) . . . . ? C7 N3 C8 C9 152.02(17) . . . . ? C15 N3 C8 C9 -60.0(2) . . . . ? N2 C8 C9 C10 178.30(19) . . . . ? N3 C8 C9 C10 -2.0(3) . . . . ? N2 C8 C9 C14 0.5(2) . . . . ? N3 C8 C9 C14 -179.72(16) . . . . ? C14 C9 C10 C11 -2.3(3) . . . . ? C8 C9 C10 C11 -179.86(19) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 -1.6(3) . . . . ? C12 C13 C14 C9 0.4(3) . . . . ? C12 C13 C14 S2 178.88(16) . . . . ? C10 C9 C14 C13 1.6(3) . . . . ? C8 C9 C14 C13 179.65(17) . . . . ? C10 C9 C14 S2 -177.20(14) . . . . ? C8 C9 C14 S2 0.88(19) . . . . ? O3 S2 C14 C13 67.4(2) . . . . ? O4 S2 C14 C13 -67.3(2) . . . . ? N2 S2 C14 C13 179.69(18) . . . . ? O3 S2 C14 C9 -113.95(14) . . . . ? O4 S2 C14 C9 111.36(15) . . . . ? N2 S2 C14 C9 -1.61(15) . . . . ? C7 N3 C15 C16 88.0(2) . . . . ? C8 N3 C15 C16 -60.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.518 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.064 #===END data_rui3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N2 O3 S' _chemical_formula_weight 288.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0020 0.0020 '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' 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1100 0.1240 '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 7.1110(10) _cell_length_b 6.8630(10) _cell_length_c 13.231(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00 _cell_volume 645.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'image plate' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4083 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 24.21 _reflns_number_total 2011 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _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 w=1/[\s^2^(Fo^2^)+(0.0379P)^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 0.51(10) _refine_ls_number_reflns 2011 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0623 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.65703(6) 0.73827(16) 0.61948(3) 0.02226(15) Uani 1 d . . . O1 O 0.5428(3) 0.5662(3) 0.62496(16) 0.0340(7) Uani 1 d . . . O2 O 0.5524(3) 0.9167(3) 0.62655(16) 0.0355(7) Uani 1 d . . . O3 O 1.29672(19) 0.7384(5) 1.11958(9) 0.0328(4) Uani 1 d . . . C2 C 0.7591(2) 0.7349(7) 0.41051(13) 0.0213(4) Uani 1 d . . . H2 H 0.6334 0.7385 0.3886 0.026 Uiso 1 calc R . . N2 N 1.1510(2) 0.7342(6) 0.70688(11) 0.0207(4) Uani 1 d . . . H15 H 1.255(3) 0.755(5) 0.6721(15) 0.025 Uiso 1 d . . . N1 N 0.82331(19) 0.7322(5) 0.70334(11) 0.0208(4) Uani 1 d . . . C7 C 0.9875(2) 0.7311(6) 0.65820(12) 0.0168(4) Uani 1 d . . . C6 C 0.9889(2) 0.7317(7) 0.54517(13) 0.0164(4) Uani 1 d . . . C3 C 0.9069(3) 0.7293(6) 0.34224(14) 0.0237(5) Uani 1 d . . . H3 H 0.8806 0.7273 0.2726 0.028 Uiso 1 calc R . . C9 C 1.3305(3) 0.8464(4) 0.84738(17) 0.0244(5) Uani 1 d . . . H9 H 1.4042 0.9170 0.8011 0.029 Uiso 1 calc R . . C5 C 1.1360(3) 0.7278(6) 0.47637(14) 0.0213(5) Uani 1 d . . . H5 H 1.2616 0.7261 0.4984 0.026 Uiso 1 calc R . . C11 C 1.2648(3) 0.7485(7) 1.01736(14) 0.0223(5) Uani 1 d . . . C4 C 1.0927(3) 0.7267(7) 0.37432(14) 0.0248(5) Uani 1 d . . . H4 H 1.1901 0.7240 0.3263 0.030 Uiso 1 calc R . . C1 C 0.8042(2) 0.7350(6) 0.51162(12) 0.0176(4) Uani 1 d . . . C8 C 1.1791(2) 0.7383(7) 0.81389(13) 0.0198(4) Uani 1 d . . . C10 C 1.3734(3) 0.8504(4) 0.94981(18) 0.0266(6) Uani 1 d . . . H10 H 1.4770 0.9230 0.9729 0.032 Uiso 1 calc R . . C12 C 1.1118(3) 0.6391(4) 0.98357(18) 0.0282(6) Uani 1 d . . . H12 H 1.0382 0.5684 1.0299 0.034 Uiso 1 calc R . . C14 C 1.4557(4) 0.8459(5) 1.15539(19) 0.0395(7) Uani 1 d . . . H14A H 1.4666 0.8299 1.2280 0.047 Uiso 1 calc R . . H14B H 1.4393 0.9828 1.1395 0.047 Uiso 1 calc R . . H14C H 1.5688 0.7978 1.1229 0.047 Uiso 1 calc R . . C13 C 1.0689(3) 0.6352(4) 0.88172(17) 0.0262(6) Uani 1 d . . . H13 H 0.9653 0.5628 0.8585 0.031 Uiso 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 0.0121(2) 0.0346(3) 0.0201(3) 0.0047(5) -0.00112(17) 0.0000(6) O1 0.0221(14) 0.052(2) 0.0280(13) 0.0088(12) -0.0039(11) -0.0203(12) O2 0.0266(14) 0.047(2) 0.0329(14) 0.0044(12) 0.0024(12) 0.0164(13) O3 0.0382(8) 0.0438(9) 0.0165(7) -0.0004(18) -0.0066(6) -0.0094(19) C2 0.0215(9) 0.0194(11) 0.0231(10) 0.005(2) -0.0063(8) 0.000(2) N2 0.0134(8) 0.0322(10) 0.0166(8) 0.0021(18) -0.0017(6) -0.002(2) N1 0.0150(8) 0.0291(10) 0.0184(8) 0.0014(18) -0.0016(6) 0.0020(19) C7 0.0160(9) 0.0162(11) 0.0184(9) 0.0020(19) -0.0012(7) 0.003(2) C6 0.0159(9) 0.0147(11) 0.0185(9) -0.0015(19) -0.0023(7) -0.005(2) C3 0.0337(11) 0.0215(12) 0.0160(9) -0.0019(19) -0.0035(8) -0.003(2) C9 0.0235(13) 0.0280(14) 0.0216(12) 0.0025(12) -0.0002(10) -0.0056(12) C5 0.0185(9) 0.0226(13) 0.0230(10) 0.002(2) -0.0016(7) -0.002(2) C11 0.0253(10) 0.0259(14) 0.0158(9) -0.0100(18) -0.0019(8) 0.007(2) C4 0.0267(10) 0.0263(14) 0.0215(10) 0.004(2) 0.0068(8) -0.003(2) C1 0.0174(9) 0.0160(10) 0.0196(10) 0.002(2) -0.0010(7) 0.000(2) C8 0.0160(9) 0.0265(11) 0.0169(9) 0.005(2) -0.0036(7) 0.000(2) C10 0.0255(13) 0.0323(15) 0.0221(12) -0.0033(12) -0.0052(10) -0.0066(12) C12 0.0281(13) 0.0337(14) 0.0228(13) 0.0055(11) 0.0003(11) -0.0048(12) C14 0.0438(16) 0.0499(18) 0.0249(14) -0.0052(13) -0.0090(12) -0.0143(15) C13 0.0212(12) 0.0310(14) 0.0263(13) -0.0012(11) -0.0049(10) -0.0060(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 O1 1.435(2) . ? S1 O2 1.436(2) . ? S1 N1 1.6221(15) . ? S1 C1 1.7699(18) . ? O3 C11 1.373(2) . ? O3 C14 1.430(3) . ? C2 C1 1.376(2) . ? C2 C3 1.386(3) . ? N2 C7 1.329(2) . ? N2 C8 1.430(2) . ? N1 C7 1.311(2) . ? C7 C6 1.496(2) . ? C6 C1 1.386(2) . ? C6 C5 1.387(3) . ? C3 C4 1.388(3) . ? C9 C8 1.381(4) . ? C9 C10 1.389(3) . ? C5 C4 1.385(3) . ? C11 C10 1.373(4) . ? C11 C12 1.396(4) . ? C8 C13 1.386(4) . ? C12 C13 1.382(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 S1 O2 113.93(9) . . ? O1 S1 N1 110.90(16) . . ? O2 S1 N1 110.78(16) . . ? O1 S1 C1 111.41(17) . . ? O2 S1 C1 111.69(17) . . ? N1 S1 C1 96.90(8) . . ? C11 O3 C14 115.5(2) . . ? C1 C2 C3 117.18(16) . . ? C7 N2 C8 127.03(16) . . ? C7 N1 S1 109.73(12) . . ? N1 C7 N2 123.91(16) . . ? N1 C7 C6 117.46(14) . . ? N2 C7 C6 118.61(16) . . ? C1 C6 C5 120.30(16) . . ? C1 C6 C7 108.31(15) . . ? C5 C6 C7 131.39(16) . . ? C2 C3 C4 121.51(16) . . ? C8 C9 C10 119.7(2) . . ? C4 C5 C6 118.18(17) . . ? C10 C11 O3 125.0(3) . . ? C10 C11 C12 120.28(19) . . ? O3 C11 C12 114.7(3) . . ? C5 C4 C3 120.65(18) . . ? C2 C1 C6 122.16(16) . . ? C2 C1 S1 130.25(13) . . ? C6 C1 S1 107.59(12) . . ? C9 C8 C13 120.51(18) . . ? C9 C8 N2 115.9(2) . . ? C13 C8 N2 123.5(3) . . ? C11 C10 C9 120.1(2) . . ? C13 C12 C11 119.7(2) . . ? C12 C13 C8 119.8(2) . . ? 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 S1 N1 C7 117.2(3) . . . . ? O2 S1 N1 C7 -115.3(3) . . . . ? C1 S1 N1 C7 1.1(4) . . . . ? S1 N1 C7 N2 177.2(4) . . . . ? S1 N1 C7 C6 -1.1(5) . . . . ? C8 N2 C7 N1 0.3(8) . . . . ? C8 N2 C7 C6 178.6(4) . . . . ? N1 C7 C6 C1 0.5(6) . . . . ? N2 C7 C6 C1 -177.9(4) . . . . ? N1 C7 C6 C5 -178.8(5) . . . . ? N2 C7 C6 C5 2.7(7) . . . . ? C1 C2 C3 C4 -0.9(7) . . . . ? C1 C6 C5 C4 -0.2(7) . . . . ? C7 C6 C5 C4 179.1(4) . . . . ? C14 O3 C11 C10 0.6(5) . . . . ? C14 O3 C11 C12 178.6(3) . . . . ? C6 C5 C4 C3 0.0(7) . . . . ? C2 C3 C4 C5 0.6(7) . . . . ? C3 C2 C1 C6 0.6(7) . . . . ? C3 C2 C1 S1 -179.2(3) . . . . ? C5 C6 C1 C2 -0.1(7) . . . . ? C7 C6 C1 C2 -179.5(4) . . . . ? C5 C6 C1 S1 179.7(3) . . . . ? C7 C6 C1 S1 0.3(4) . . . . ? O1 S1 C1 C2 63.3(5) . . . . ? O2 S1 C1 C2 -65.3(5) . . . . ? N1 S1 C1 C2 179.0(5) . . . . ? O1 S1 C1 C6 -116.5(3) . . . . ? O2 S1 C1 C6 114.8(3) . . . . ? N1 S1 C1 C6 -0.8(4) . . . . ? C10 C9 C8 C13 0.5(5) . . . . ? C10 C9 C8 N2 -176.9(3) . . . . ? C7 N2 C8 C9 -144.3(4) . . . . ? C7 N2 C8 C13 38.4(7) . . . . ? O3 C11 C10 C9 178.4(3) . . . . ? C12 C11 C10 C9 0.6(5) . . . . ? C8 C9 C10 C11 -0.5(4) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? O3 C11 C12 C13 -178.7(3) . . . . ? C11 C12 C13 C8 0.6(4) . . . . ? C9 C8 C13 C12 -0.6(5) . . . . ? N2 C8 C13 C12 176.6(3) . . . . ? 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 N2 H15 O2 0.88(2) 2.47(3) 3.294(3) 157(3) 1_655 N2 H15 O1 0.88(2) 2.50(2) 3.204(3) 137(3) 1_655 N2 H15 S1 0.88(2) 2.95(2) 3.7797(18) 159(2) 1_655 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 24.21 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.212 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.041 #===END data_liv2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 N3 O5 S2' _chemical_formula_weight 453.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1028(8) _cell_length_b 8.3652(8) _cell_length_c 15.7507(16) _cell_angle_alpha 96.111(3) _cell_angle_beta 90.830(3) _cell_angle_gamma 93.793(3) _cell_volume 1058.97(18) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 4258 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.60 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.92 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6493 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.63 _reflns_number_total 4706 _reflns_number_gt 3613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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 w=1/[\s^2^(Fo^2^)+(0.0625P)^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_number_reflns 4706 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.24262(6) 0.53833(6) 0.57558(3) 0.02536(14) Uani 1 d . . . S2 S 0.55418(5) 0.74071(6) 0.94595(3) 0.02339(13) Uani 1 d . . . O1 O 0.32184(19) 0.62497(16) 0.51230(9) 0.0376(4) Uani 1 d . . . O2 O 0.07593(17) 0.56997(16) 0.59638(9) 0.0331(3) Uani 1 d . . . O3 O 0.61222(17) 0.89784(16) 0.92628(9) 0.0346(4) Uani 1 d . . . O4 O 0.60207(16) 0.69242(17) 1.02647(8) 0.0307(3) Uani 1 d . . . O5 O 1.0378(2) 0.0458(2) 0.71364(10) 0.0479(4) Uani 1 d . . . N1 N 0.35754(19) 0.56711(18) 0.66546(9) 0.0246(4) Uani 1 d . . . N2 N 0.61271(18) 0.60658(19) 0.86749(9) 0.0251(4) Uani 1 d . . . N3 N 0.49914(19) 0.42215(19) 0.75750(10) 0.0239(4) Uani 1 d . . . C1 C 0.4092(2) 0.4313(2) 0.68233(11) 0.0221(4) Uani 1 d . . . C2 C 0.3651(2) 0.2861(2) 0.62130(11) 0.0210(4) Uani 1 d . . . C3 C 0.3971(2) 0.1265(2) 0.62289(13) 0.0283(4) Uani 1 d . . . H3 H 0.4636 0.0939 0.6673 0.034 Uiso 1 calc R . . C4 C 0.3296(3) 0.0145(2) 0.55804(14) 0.0339(5) Uani 1 d . . . H4 H 0.3511 -0.0958 0.5580 0.041 Uiso 1 calc R . . C5 C 0.2318(3) 0.0608(3) 0.49356(14) 0.0364(5) Uani 1 d . . . H5 H 0.1871 -0.0183 0.4501 0.044 Uiso 1 calc R . . C6 C 0.1974(2) 0.2210(2) 0.49115(12) 0.0308(5) Uani 1 d . . . H6 H 0.1297 0.2537 0.4473 0.037 Uiso 1 calc R . . C7 C 0.2670(2) 0.3300(2) 0.55594(11) 0.0224(4) Uani 1 d . . . C8 C 0.4834(2) 0.5407(2) 0.82584(11) 0.0213(4) Uani 1 d . . . C9 C 0.3197(2) 0.5837(2) 0.85730(11) 0.0220(4) Uani 1 d . . . C10 C 0.1619(2) 0.5162(2) 0.83388(12) 0.0265(4) Uani 1 d . . . H10 H 0.1459 0.4340 0.7875 0.032 Uiso 1 calc R . . C11 C 0.0292(2) 0.5711(2) 0.87954(13) 0.0314(5) Uani 1 d . . . H11 H -0.0791 0.5258 0.8643 0.038 Uiso 1 calc R . . C12 C 0.0510(2) 0.6914(3) 0.94736(13) 0.0320(5) Uani 1 d . . . H12 H -0.0426 0.7282 0.9774 0.038 Uiso 1 calc R . . C13 C 0.2084(2) 0.7589(2) 0.97193(12) 0.0274(4) Uani 1 d . . . H13 H 0.2247 0.8413 1.0183 0.033 Uiso 1 calc R . . C14 C 0.3390(2) 0.7013(2) 0.92632(11) 0.0214(4) Uani 1 d . . . C15 C 0.6442(2) 0.3297(2) 0.75196(11) 0.0225(4) Uani 1 d . . . C16 C 0.6598(2) 0.2088(2) 0.80354(12) 0.0294(5) Uani 1 d . . . H16 H 0.5803 0.1920 0.8460 0.035 Uiso 1 calc R . . C17 C 0.7919(3) 0.1109(3) 0.79365(12) 0.0325(5) Uani 1 d . . . H17 H 0.8034 0.0274 0.8293 0.039 Uiso 1 calc R . . C18 C 0.9068(2) 0.1363(2) 0.73116(12) 0.0293(4) Uani 1 d . . . C19 C 0.8904(2) 0.2604(2) 0.68010(12) 0.0260(4) Uani 1 d . . . H19 H 0.9698 0.2783 0.6378 0.031 Uiso 1 calc R . . C20 C 0.7599(2) 0.3572(2) 0.69060(11) 0.0225(4) Uani 1 d . . . H20 H 0.7493 0.4423 0.6559 0.027 Uiso 1 calc R . . C21 C 1.0590(4) -0.0870(4) 0.76192(19) 0.0747(10) Uani 1 d . . . H21A H 1.0808 -0.0468 0.8220 0.112 Uiso 1 calc R . . H21B H 1.1526 -0.1460 0.7398 0.112 Uiso 1 calc R . . H21C H 0.9582 -0.1591 0.7570 0.112 Uiso 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 0.0319(3) 0.0248(3) 0.0193(2) 0.00213(19) -0.00213(19) 0.0026(2) S2 0.0175(2) 0.0309(3) 0.0199(2) -0.00292(19) 0.00098(17) -0.00269(19) O1 0.0566(10) 0.0301(8) 0.0268(8) 0.0101(6) 0.0022(7) -0.0019(7) O2 0.0331(8) 0.0351(8) 0.0314(8) 0.0005(6) -0.0049(6) 0.0109(6) O3 0.0341(8) 0.0326(8) 0.0339(8) -0.0035(6) 0.0069(6) -0.0111(6) O4 0.0247(7) 0.0450(9) 0.0213(7) -0.0011(6) -0.0041(6) 0.0024(6) O5 0.0454(10) 0.0601(11) 0.0449(10) 0.0170(8) 0.0177(8) 0.0309(8) N1 0.0289(9) 0.0244(9) 0.0199(8) 0.0004(6) -0.0015(7) 0.0006(7) N2 0.0178(8) 0.0346(9) 0.0212(8) -0.0038(7) 0.0019(6) 0.0003(7) N3 0.0198(8) 0.0306(9) 0.0207(8) -0.0026(7) -0.0019(6) 0.0053(7) C1 0.0200(9) 0.0275(10) 0.0183(9) 0.0004(7) 0.0019(7) 0.0008(8) C2 0.0193(9) 0.0245(10) 0.0185(9) 0.0001(7) 0.0025(7) -0.0004(7) C3 0.0281(11) 0.0262(10) 0.0304(11) 0.0014(8) 0.0004(8) 0.0025(8) C4 0.0330(12) 0.0235(11) 0.0433(13) -0.0052(9) 0.0036(9) 0.0014(9) C5 0.0350(12) 0.0338(12) 0.0356(12) -0.0136(9) -0.0017(9) -0.0039(9) C6 0.0288(11) 0.0378(12) 0.0237(10) -0.0051(9) -0.0026(8) 0.0001(9) C7 0.0213(9) 0.0239(10) 0.0216(9) 0.0015(7) 0.0029(7) 0.0003(7) C8 0.0211(9) 0.0252(10) 0.0173(9) 0.0014(7) 0.0002(7) 0.0015(7) C9 0.0203(9) 0.0269(10) 0.0192(9) 0.0047(8) -0.0012(7) 0.0014(7) C10 0.0210(10) 0.0326(11) 0.0244(10) -0.0008(8) -0.0031(8) -0.0021(8) C11 0.0182(10) 0.0427(13) 0.0328(11) 0.0052(9) -0.0034(8) -0.0014(9) C12 0.0203(10) 0.0458(13) 0.0305(11) 0.0029(9) 0.0033(8) 0.0083(9) C13 0.0246(10) 0.0343(11) 0.0231(10) -0.0003(8) 0.0008(8) 0.0052(8) C14 0.0184(9) 0.0268(10) 0.0190(9) 0.0032(7) -0.0011(7) 0.0019(7) C15 0.0191(9) 0.0283(10) 0.0193(9) -0.0018(8) -0.0001(7) 0.0026(8) C16 0.0285(11) 0.0418(12) 0.0193(10) 0.0059(9) 0.0063(8) 0.0067(9) C17 0.0376(12) 0.0408(12) 0.0221(10) 0.0110(9) 0.0054(9) 0.0118(10) C18 0.0277(11) 0.0358(12) 0.0246(10) -0.0001(8) 0.0036(8) 0.0090(9) C19 0.0245(10) 0.0312(11) 0.0209(10) -0.0015(8) 0.0048(8) -0.0033(8) C20 0.0239(10) 0.0234(10) 0.0192(9) 0.0000(7) -0.0010(7) -0.0017(8) C21 0.082(2) 0.085(2) 0.071(2) 0.0359(17) 0.0243(17) 0.0592(18) _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 O1 1.4287(14) . ? S1 O2 1.4295(15) . ? S1 N1 1.6700(15) . ? S1 C7 1.7620(19) . ? S2 O4 1.4276(13) . ? S2 O3 1.4331(14) . ? S2 N2 1.6742(16) . ? S2 C14 1.7690(18) . ? O5 C18 1.359(2) . ? O5 C21 1.429(3) . ? N1 C1 1.288(2) . ? N2 C8 1.288(2) . ? N3 C1 1.393(2) . ? N3 C8 1.397(2) . ? N3 C15 1.448(2) . ? C1 C2 1.487(3) . ? C2 C3 1.379(3) . ? C2 C7 1.387(2) . ? C3 C4 1.390(3) . ? C4 C5 1.383(3) . ? C5 C6 1.391(3) . ? C6 C7 1.381(3) . ? C8 C9 1.477(3) . ? C9 C14 1.386(3) . ? C9 C10 1.392(2) . ? C10 C11 1.379(3) . ? C11 C12 1.388(3) . ? C12 C13 1.392(3) . ? C13 C14 1.373(3) . ? C15 C16 1.374(3) . ? C15 C20 1.382(3) . ? C16 C17 1.391(3) . ? C17 C18 1.387(3) . ? C18 C19 1.391(3) . ? C19 C20 1.376(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 S1 O2 118.30(9) . . ? O1 S1 N1 109.01(8) . . ? O2 S1 N1 108.31(8) . . ? O1 S1 C7 111.41(9) . . ? O2 S1 C7 111.57(8) . . ? N1 S1 C7 95.82(8) . . ? O4 S2 O3 117.99(8) . . ? O4 S2 N2 109.35(8) . . ? O3 S2 N2 107.68(8) . . ? O4 S2 C14 111.08(8) . . ? O3 S2 C14 112.47(8) . . ? N2 S2 C14 95.88(8) . . ? C18 O5 C21 118.20(19) . . ? C1 N1 S1 109.21(12) . . ? C8 N2 S2 109.14(13) . . ? C1 N3 C8 118.61(15) . . ? C1 N3 C15 117.57(15) . . ? C8 N3 C15 120.11(14) . . ? N1 C1 N3 120.05(16) . . ? N1 C1 C2 118.28(15) . . ? N3 C1 C2 121.64(16) . . ? C3 C2 C7 119.49(17) . . ? C3 C2 C1 131.72(16) . . ? C7 C2 C1 108.66(16) . . ? C2 C3 C4 118.43(18) . . ? C5 C4 C3 121.14(19) . . ? C4 C5 C6 121.26(19) . . ? C7 C6 C5 116.46(18) . . ? C6 C7 C2 123.23(18) . . ? C6 C7 S1 128.70(15) . . ? C2 C7 S1 107.99(13) . . ? N2 C8 N3 120.32(16) . . ? N2 C8 C9 117.98(16) . . ? N3 C8 C9 121.48(15) . . ? C14 C9 C10 119.29(18) . . ? C14 C9 C8 109.80(15) . . ? C10 C9 C8 130.60(17) . . ? C11 C10 C9 118.53(18) . . ? C10 C11 C12 121.25(18) . . ? C11 C12 C13 120.76(19) . . ? C14 C13 C12 117.12(18) . . ? C13 C14 C9 123.02(17) . . ? C13 C14 S2 129.70(15) . . ? C9 C14 S2 107.04(14) . . ? C16 C15 C20 120.78(18) . . ? C16 C15 N3 119.82(17) . . ? C20 C15 N3 119.25(17) . . ? C15 C16 C17 120.06(19) . . ? C18 C17 C16 119.36(18) . . ? O5 C18 C17 124.80(19) . . ? O5 C18 C19 115.26(18) . . ? C17 C18 C19 119.93(18) . . ? C20 C19 C18 120.34(18) . . ? C19 C20 C15 119.51(17) . . ? 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 S1 N1 C1 -116.43(14) . . . . ? O2 S1 N1 C1 113.62(14) . . . . ? C7 S1 N1 C1 -1.40(15) . . . . ? O4 S2 N2 C8 117.66(13) . . . . ? O3 S2 N2 C8 -112.98(14) . . . . ? C14 S2 N2 C8 2.87(14) . . . . ? S1 N1 C1 N3 -175.84(14) . . . . ? S1 N1 C1 C2 2.1(2) . . . . ? C8 N3 C1 N1 22.2(3) . . . . ? C15 N3 C1 N1 -136.13(18) . . . . ? C8 N3 C1 C2 -155.66(17) . . . . ? C15 N3 C1 C2 46.0(2) . . . . ? N1 C1 C2 C3 -177.80(19) . . . . ? N3 C1 C2 C3 0.1(3) . . . . ? N1 C1 C2 C7 -1.9(2) . . . . ? N3 C1 C2 C7 176.06(16) . . . . ? C7 C2 C3 C4 0.3(3) . . . . ? C1 C2 C3 C4 175.88(19) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 0.4(3) . . . . ? C5 C6 C7 C2 -0.6(3) . . . . ? C5 C6 C7 S1 -176.84(16) . . . . ? C3 C2 C7 C6 0.2(3) . . . . ? C1 C2 C7 C6 -176.31(18) . . . . ? C3 C2 C7 S1 177.16(15) . . . . ? C1 C2 C7 S1 0.64(18) . . . . ? O1 S1 C7 C6 -69.9(2) . . . . ? O2 S1 C7 C6 64.8(2) . . . . ? N1 S1 C7 C6 177.09(18) . . . . ? O1 S1 C7 C2 113.42(14) . . . . ? O2 S1 C7 C2 -111.96(13) . . . . ? N1 S1 C7 C2 0.37(14) . . . . ? S2 N2 C8 N3 -179.11(13) . . . . ? S2 N2 C8 C9 -4.4(2) . . . . ? C1 N3 C8 N2 -134.57(18) . . . . ? C15 N3 C8 N2 23.2(3) . . . . ? C1 N3 C8 C9 50.9(2) . . . . ? C15 N3 C8 C9 -151.28(16) . . . . ? N2 C8 C9 C14 4.0(2) . . . . ? N3 C8 C9 C14 178.66(16) . . . . ? N2 C8 C9 C10 -169.40(18) . . . . ? N3 C8 C9 C10 5.2(3) . . . . ? C14 C9 C10 C11 1.2(3) . . . . ? C8 C9 C10 C11 174.10(18) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C13 -0.8(3) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C9 1.4(3) . . . . ? C12 C13 C14 S2 -172.14(15) . . . . ? C10 C9 C14 C13 -2.0(3) . . . . ? C8 C9 C14 C13 -176.31(16) . . . . ? C10 C9 C14 S2 172.77(13) . . . . ? C8 C9 C14 S2 -1.51(18) . . . . ? O4 S2 C14 C13 60.3(2) . . . . ? O3 S2 C14 C13 -74.40(19) . . . . ? N2 S2 C14 C13 173.70(18) . . . . ? O4 S2 C14 C9 -114.00(13) . . . . ? O3 S2 C14 C9 111.27(13) . . . . ? N2 S2 C14 C9 -0.63(14) . . . . ? C1 N3 C15 C16 -125.93(19) . . . . ? C8 N3 C15 C16 76.0(2) . . . . ? C1 N3 C15 C20 49.7(2) . . . . ? C8 N3 C15 C20 -108.33(19) . . . . ? C20 C15 C16 C17 -0.9(3) . . . . ? N3 C15 C16 C17 174.70(17) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C21 O5 C18 C17 0.8(3) . . . . ? C21 O5 C18 C19 -178.1(2) . . . . ? C16 C17 C18 O5 -177.86(19) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? O5 C18 C19 C20 178.29(17) . . . . ? C17 C18 C19 C20 -0.7(3) . . . . ? C18 C19 C20 C15 -0.4(3) . . . . ? C16 C15 C20 C19 1.2(3) . . . . ? N3 C15 C20 C19 -174.39(16) . . . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.326 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.057 #===END data_liv1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N2 O2 S' _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' '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' '0.5-x, 0.5+y, 0.5-z' '0.5+x, 0.5-y, 0.5+z' _cell_length_a 7.2916(16) _cell_length_b 21.129(5) _cell_length_c 8.0546(18) _cell_angle_alpha 90 _cell_angle_beta 97.246(5) _cell_angle_gamma 90 _cell_volume 1231.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 6167 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 26.69 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.6879 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 15 _diffrn_reflns_number 7195 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2654 _reflns_number_gt 2377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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 w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.2824P] 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 2654 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.79844(5) 0.033006(17) 0.76764(5) 0.01585(14) Uani 1 d . . . O1 O 0.91908(16) 0.01337(6) 0.64822(14) 0.0228(3) Uani 1 d . . . O2 O 0.88688(16) 0.06427(6) 0.91317(14) 0.0237(3) Uani 1 d . . . N1 N 0.63144(18) 0.07704(6) 0.67445(16) 0.0183(3) Uani 1 d . . . N2 N 0.30873(18) 0.07265(6) 0.60794(16) 0.0177(3) Uani 1 d . . . H2 H 0.2115 0.0489 0.6174 0.021 Uiso 1 calc R . . C1 C 0.6568(2) -0.03036(7) 0.81661(19) 0.0162(3) Uani 1 d . . . C2 C 0.7048(2) -0.08629(8) 0.8998(2) 0.0210(3) Uani 1 d . . . H2A H 0.8295 -0.0959 0.9411 0.025 Uiso 1 calc R . . C3 C 0.5610(2) -0.12773(8) 0.9199(2) 0.0232(4) Uani 1 d . . . H3 H 0.5878 -0.1666 0.9771 0.028 Uiso 1 calc R . . C4 C 0.3791(2) -0.11350(8) 0.8583(2) 0.0225(4) Uani 1 d . . . H4 H 0.2843 -0.1430 0.8735 0.027 Uiso 1 calc R . . C5 C 0.3332(2) -0.05693(8) 0.7746(2) 0.0197(3) Uani 1 d . . . H5 H 0.2087 -0.0473 0.7324 0.024 Uiso 1 calc R . . C6 C 0.4755(2) -0.01508(7) 0.7548(18) 0.0153(3) Uani 1 d . . . C7 C 0.4712(2) 0.04841(7) 0.67418(18) 0.0155(3) Uani 1 d . . . C8 C 0.2711(2) 0.13136(7) 0.52454(19) 0.0177(3) Uani 1 d . . . C9 C 0.4089(2) 0.17407(7) 0.4953(2) 0.0207(3) Uani 1 d . . . H9 H 0.5349 0.1644 0.5313 0.025 Uiso 1 calc R . . C10 C 0.3623(2) 0.23107(8) 0.4132(2) 0.0230(4) Uani 1 d . . . C11 C 0.1770(3) 0.24445(8) 0.3613(2) 0.0272(4) Uani 1 d . . . H11 H 0.1438 0.2833 0.3060 0.033 Uiso 1 calc R . . C12 C 0.0400(3) 0.20144(9) 0.3896(2) 0.0297(4) Uani 1 d . . . H12 H -0.0859 0.2110 0.3530 0.036 Uiso 1 calc R . . C13 C 0.0855(2) 0.14471(8) 0.4708(2) 0.0239(4) Uani 1 d . . . H13 H -0.0082 0.1153 0.4897 0.029 Uiso 1 calc R . . C14 C 0.5130(3) 0.27624(9) 0.3795(3) 0.0345(4) Uani 1 d . . . H14A H 0.5639 0.2631 0.2780 0.052 Uiso 1 calc R . . H14B H 0.6112 0.2760 0.4745 0.052 Uiso 1 calc R . . H14C H 0.4619 0.3190 0.3640 0.052 Uiso 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 0.0091(2) 0.0167(2) 0.0216(2) -0.00006(13) 0.00112(15) -0.00132(13) O1 0.0146(6) 0.0259(6) 0.0291(6) -0.0029(5) 0.0075(5) -0.0017(5) O2 0.0171(6) 0.0235(6) 0.0288(6) -0.0037(5) -0.0041(5) -0.0031(5) N1 0.0115(6) 0.0189(7) 0.0238(7) 0.0030(5) -0.0003(5) -0.0002(5) N2 0.0108(6) 0.0166(6) 0.0249(7) 0.0020(5) -0.0009(5) -0.0020(5) C1 0.0129(7) 0.0168(8) 0.0190(7) -0.0010(6) 0.0025(6) -0.0028(6) C2 0.0154(8) 0.0210(8) 0.0259(8) 0.0025(6) -0.0005(6) -.0016(6) C3 0.0224(9) 0.0181(8) 0.0293(8) 0.0051(6) 0.0037(7) 0.0012(6) C4 0.0182(8) 0.0193(8) 0.0310(9) 0.0008(6) 0.0064(7) -0.0039(6) C5 0.0117(7) 0.0215(8) 0.0261(8) 0.0000(6) 0.0032(6) -0.0001(6) C6 0.0128(7) 0.0165(7) 0.0167(7) -0.0018(6) 0.0019(5) 0.0008(6) C7 0.0139(7) 0.0161(7) 0.0164(7) -0.0022(6) 0.0013(5) -0.0005(6) C8 0.0181(8) 0.0159(7) 0.0184(7) -0.0015(6) -0.0008(6) 0.0025(6) C9 0.0198(8) 0.0182(8) 0.0230(8) -0.0007(6) -0.0013(6) 0.0001(6) C10 0.0280(9) 0.0159(8) 0.0246(8) 0.0001(6) 0.0010(7) 0.0013(6) C11 0.0320(10) 0.0198(8) 0.0282(8) 0.0023(7) -0.0026(7) 0.0070(7) C12 0.0221(9) 0.0285(9) 0.0361(10) 0.0010(7) -0.0054(7) 0.0083(7) C13 0.0166(8) 0.0236(8) 0.0305(9) -0.0008(7) -0.0009(7) 0.0016(7) C14 0.0351(11) 0.0212(9) 0.0467(11) 0.0088(8) 0.0030(9) -0.0029(8) _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 O2 1.4268(12) . ? S1 O1 1.4438(12) . ? S1 N1 1.6374(13) . ? S1 C1 1.7657(16) . ? N1 C7 1.315(2) . ? N2 C7 1.338(2) . ? N2 C8 1.421(2) . ? C1 C2 1.382(2) . ? C1 C6 1.391(2) . ? C2 C3 1.391(2) . ? C3 C4 1.389(2) . ? C4 C5 1.392(2) . ? C5 C6 1.387(2) . ? C6 C7 1.489(2) . ? C8 C9 1.392(2) . ? C8 C13 1.397(2) . ? C9 C10 1.395(2) . ? C10 C11 1.392(3) . ? C10 C14 1.506(3) . ? C11 C12 1.390(3) . ? C12 C13 1.386(2) . ? 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 O2 S1 O1 115.48(7) . . ? O2 S1 N1 110.27(7) . . ? O1 S1 N1 109.77(7) . . ? O2 S1 C1 112.58(7) . . ? O1 S1 C1 110.71(7) . . ? N1 S1 C1 96.38(7) . . ? C7 N1 S1 110.39(11) . . ? C7 N2 C8 129.11(14) . . ? C2 C1 C6 122.92(15) . . ? C2 C1 S1 129.59(13) . . ? C6 C1 S1 107.48(11) . . ? C1 C2 C3 116.51(15) . . ? C4 C3 C2 121.45(15) . . ? C3 C4 C5 121.30(16) . . ? C6 C5 C4 117.70(15) . . ? C5 C6 C1 120.12(14) . . ? C5 C6 C7 130.50(14) . . ? C1 C6 C7 109.38(13) . . ? N1 C7 N2 124.48(14) . . ? N1 C7 C6 116.36(13) . . ? N2 C7 C6 119.16(14) . . ? C9 C8 C13 120.56(15) . . ? C9 C8 N2 123.05(14) . . ? C13 C8 N2 116.39(15) . . ? C8 C9 C10 120.09(16) . . ? C11 C10 C9 119.16(16) . . ? C11 C10 C14 121.32(15) . . ? C9 C10 C14 119.51(16) . . ? C12 C11 C10 120.52(16) . . ? C13 C12 C11 120.60(16) . . ? C12 C13 C8 119.07(17) . . ? _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.502 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.057 #===END data_liv5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N5 O' _chemical_formula_weight 267.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 17.689(3) _cell_length_b 6.6556(13) _cell_length_c 11.735(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.61(2) _cell_angle_gamma 90.00 _cell_volume 1330.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 52 _cell_measurement_theta_min 20.57 _cell_measurement_theta_max 24.87 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.732 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.967 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 4296 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 67.48 _reflns_number_total 2290 _reflns_number_gt 1897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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 w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.3732P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2290 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.21461(10) 0.8030(2) 0.37908(12) 0.0237(4) Uani 1 d . . . N1 N 0.18833(9) 0.8140(2) 0.47479(10) 0.0278(3) Uani 1 d . . . N2 N 0.23083(9) 0.6736(2) 0.54952(10) 0.0299(4) Uani 1 d . . . N3 N 0.28018(9) 0.5800(2) 0.50536(10) 0.0314(4) Uani 1 d . . . N4 N 0.27134(8) 0.6633(2) 0.39567(10) 0.0261(3) Uani 1 d . . . N5 N 0.19072(9) 0.9095(2) 0.27719(10) 0.0318(4) Uani 1 d . . . H5 H 0.2079 0.8692 0.2173 0.038 Uiso 1 calc R . . C2 C 0.14118(10) 1.0779(3) 0.25817(12) 0.0259(4) Uani 1 d . . . C3 C 0.09850(11) 1.1177(3) 0.14238(13) 0.0379(5) Uani 1 d . . . H3 H 0.1004 1.0265 0.0810 0.045 Uiso 1 calc R . . C4 C 0.05350(13) 1.2887(4) 0.11657(15) 0.0486(6) Uani 1 d . . . H4 H 0.0247 1.3151 0.0372 0.058 Uiso 1 calc R . . C5 C 0.04968(12) 1.4234(3) 0.20543(15) 0.0422(5) Uani 1 d . . . H5A H 0.0193 1.5426 0.1872 0.051 Uiso 1 calc R . . C6 C 0.09062(11) 1.3810(3) 0.32026(14) 0.0333(4) Uani 1 d . . . H6 H 0.0874 1.4710 0.3816 0.040 Uiso 1 calc R . . C7 C 0.13634(10) 1.2100(3) 0.34806(12) 0.0274(4) Uani 1 d . . . H7 H 0.1642 1.1828 0.4278 0.033 Uiso 1 calc R . . C8 C 0.31598(10) 0.6000(3) 0.31643(12) 0.0248(4) Uani 1 d . . . C9 C 0.28807(10) 0.4462(3) 0.23745(13) 0.0288(4) Uani 1 d . . . H9 H 0.2405 0.3801 0.2377 0.035 Uiso 1 calc R . . C10 C 0.32946(10) 0.3877(3) 0.15741(13) 0.0283(4) Uani 1 d . . . H10 H 0.3111 0.2797 0.1042 0.034 Uiso 1 calc R . . C11 C 0.39780(10) 0.4890(3) 0.15645(12) 0.0256(4) Uani 1 d . . . C12 C 0.42597(11) 0.6430(3) 0.23695(14) 0.0343(4) Uani 1 d . . . H12 H 0.4733 0.7102 0.2368 0.041 Uiso 1 calc R . . C13 C 0.38504(10) 0.6984(3) 0.31724(14) 0.0323(4) Uani 1 d . . . H13 H 0.4042 0.8031 0.3725 0.039 Uiso 1 calc R . . O1 O 0.44167(7) 0.4495(2) 0.07928(9) 0.0332(3) Uani 1 d . . . C14 C 0.41438(12) 0.2919(3) -0.00483(16) 0.0416(5) Uani 1 d . . . H14A H 0.4125 0.1655 0.0371 0.062 Uiso 1 calc R . . H14B H 0.4502 0.2776 -0.0551 0.062 Uiso 1 calc R . . H14C H 0.3617 0.3249 -0.0541 0.062 Uiso 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 C1 0.0296(9) 0.0254(9) 0.0197(6) -0.0012(6) 0.0131(6) -0.0020(7) N1 0.0371(8) 0.0312(8) 0.0199(6) 0.0004(5) 0.0159(5) 0.0005(7) N2 0.0410(9) 0.0316(8) 0.0221(6) 0.0016(5) 0.0170(6) -0.0007(7) N3 0.0454(9) 0.0331(8) 0.0204(6) 0.0043(6) 0.0167(6) 0.0014(7) N4 0.0352(8) 0.0288(8) 0.0186(6) 0.0038(5) 0.0149(5) 0.0020(6) N5 0.0462(9) 0.0359(9) 0.0190(6) 0.0035(6) 0.0187(6) 0.0121(7) C2 0.0276(9) 0.0310(9) 0.0237(7) 0.0028(6) 0.0149(6) 0.0005(7) C3 0.0462(11) 0.0487(12) 0.0215(7) -0.0003(7) 0.0138(7) 0.0113(9) C4 0.0577(14) 0.0630(15) 0.0271(8) 0.0089(8) 0.0148(8) 0.0258(11) C5 0.0496(12) 0.0447(12) 0.0388(9) 0.0112(8) 0.0234(8) 0.0195(10) C6 0.0389(10) 0.0342(10) 0.0337(8) -0.0022(7) 0.0215(7) 0.0023(8) C7 0.0292(9) 0.0338(10) 0.0226(7) -0.0011(6) 0.0131(6) -0.0017(7) C8 0.0295(9) 0.0277(9) 0.0214(7) 0.0016(6) 0.0142(6) 0.0026(7) C9 0.0308(10) 0.0317(9) 0.0287(7) -0.0003(6) 0.0167(7) -0.0061(7) C10 0.0329(9) 0.0284(9) 0.0265(7) -0.0045(6) 0.0132(6) -0.0048(8) C11 0.0286(9) 0.0280(9) 0.0243(7) 0.0006(6) 0.0139(6) 0.0013(7) C12 0.0314(10) 0.0381(11) 0.0390(8) -0.0084(8) 0.0190(7) -0.0098(8) C13 0.0348(10) 0.0342(10) 0.0314(8) -0.0089(7) 0.0152(7) -0.0063(8) O1 0.0361(7) 0.0372(7) 0.0346(6) -0.0110(5) 0.0237(5) -0.0073(6) C14 0.0506(12) 0.0447(12) 0.0395(9) -0.0175(8) 0.0294(8) -0.0115(10) _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 N1 1.3280(19) . ? C1 N4 1.343(2) . ? C1 N5 1.3559(19) . ? N1 N2 1.361(2) . ? N2 N3 1.289(2) . ? N3 N4 1.3713(17) . ? N4 C8 1.4357(19) . ? N5 C2 1.403(2) . ? C2 C3 1.391(2) . ? C2 C7 1.393(2) . ? C3 C4 1.375(3) . ? C4 C5 1.391(3) . ? C5 C6 1.376(2) . ? C6 C7 1.384(3) . ? C8 C9 1.380(2) . ? C8 C13 1.384(2) . ? C9 C10 1.393(2) . ? C10 C11 1.387(2) . ? C11 O1 1.3674(19) . ? C11 C12 1.392(2) . ? C12 C13 1.384(2) . ? O1 C14 1.432(2) . ? 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 N1 C1 N4 109.47(13) . . ? N1 C1 N5 128.32(15) . . ? N4 C1 N5 122.21(14) . . ? C1 N1 N2 104.42(13) . . ? N3 N2 N1 112.90(12) . . ? N2 N3 N4 105.27(13) . . ? C1 N4 N3 107.94(13) . . ? C1 N4 C8 128.98(13) . . ? N3 N4 C8 123.07(14) . . ? C1 N5 C2 126.22(13) . . ? C3 C2 C7 119.45(16) . . ? C3 C2 N5 117.34(14) . . ? C7 C2 N5 123.13(14) . . ? C4 C3 C2 120.18(17) . . ? C3 C4 C5 120.69(16) . . ? C6 C5 C4 118.90(18) . . ? C5 C6 C7 121.29(16) . . ? C6 C7 C2 119.46(14) . . ? C9 C8 C13 120.76(15) . . ? C9 C8 N4 119.54(15) . . ? C13 C8 N4 119.66(15) . . ? C8 C9 C10 120.16(16) . . ? C11 C10 C9 119.13(15) . . ? O1 C11 C10 124.27(15) . . ? O1 C11 C12 115.32(15) . . ? C10 C11 C12 120.41(15) . . ? C13 C12 C11 120.05(16) . . ? C12 C13 C8 119.46(16) . . ? C11 O1 C14 116.81(13) . . ? 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 N4 C1 N1 N2 -0.67(18) . . . . ? N5 C1 N1 N2 178.91(16) . . . . ? C1 N1 N2 N3 -0.13(19) . . . . ? N1 N2 N3 N4 0.84(19) . . . . ? N1 C1 N4 N3 1.19(19) . . . . ? N5 C1 N4 N3 -178.42(15) . . . . ? N1 C1 N4 C8 179.68(16) . . . . ? N5 C1 N4 C8 0.1(3) . . . . ? N2 N3 N4 C1 -1.22(18) . . . . ? N2 N3 N4 C8 -179.81(15) . . . . ? N1 C1 N5 C2 10.9(3) . . . . ? N4 C1 N5 C2 -169.57(16) . . . . ? C1 N5 C2 C3 -154.74(18) . . . . ? C1 N5 C2 C7 28.7(3) . . . . ? C7 C2 C3 C4 1.7(3) . . . . ? N5 C2 C3 C4 -175.05(19) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C4 C5 C6 C7 1.3(3) . . . . ? C5 C6 C7 C2 0.1(3) . . . . ? C3 C2 C7 C6 -1.5(3) . . . . ? N5 C2 C7 C6 174.97(16) . . . . ? C1 N4 C8 C9 -89.0(2) . . . . ? N3 N4 C8 C9 89.3(2) . . . . ? C1 N4 C8 C13 88.8(2) . . . . ? N3 N4 C8 C13 -92.9(2) . . . . ? C13 C8 C9 C10 0.2(3) . . . . ? N4 C8 C9 C10 177.88(14) . . . . ? C8 C9 C10 C11 -1.5(2) . . . . ? C9 C10 C11 O1 -177.61(15) . . . . ? C9 C10 C11 C12 2.0(2) . . . . ? O1 C11 C12 C13 178.50(16) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? N4 C8 C13 C12 -177.00(16) . . . . ? C10 C11 O1 C14 -0.3(2) . . . . ? C12 C11 O1 C14 -179.99(16) . . . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 67.48 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.218 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.040 #===END OF ALL