# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compd-16 #TrackingRef 'kckcif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 Cl N3 O2' _chemical_formula_weight 327.76 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' Cl Cl 0.1484 0.1585 '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 11.1770(11) _cell_length_b 5.4737(4) _cell_length_c 25.780(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.299(9) _cell_angle_gamma 90.00 _cell_volume 1551.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 832 _cell_measurement_theta_min 3.2062 _cell_measurement_theta_max 28.9582 __exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92801 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5239 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2742 _reflns_number_gt 1367 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2742 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1279 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.47192(10) -0.0426(2) 1.09291(4) 0.0944(5) Uani 1 1 d . . . O1 O 0.1084(2) 0.7106(5) 1.02150(10) 0.0741(8) Uani 1 1 d . . . C11 C -0.0747(3) 1.0333(6) 0.80799(13) 0.0521(9) Uani 1 1 d . . . C6 C 0.2841(3) 0.4813(6) 1.00823(14) 0.0548(9) Uani 1 1 d . . . C1 C 0.1967(3) 0.5409(7) 1.03781(15) 0.0607(10) Uani 1 1 d . . . N1 N 0.0927(3) 0.9480(5) 0.85991(12) 0.0618(8) Uani 1 1 d . . . O2 O 0.2877(2) 0.5929(5) 0.96069(10) 0.0747(8) Uani 1 1 d . . . N3 N -0.0311(3) 1.2381(5) 0.83513(13) 0.0717(9) Uani 1 1 d . . . C10 C 0.0053(3) 0.8504(6) 0.82405(13) 0.0559(9) Uani 1 1 d . . . H10 H 0.0000 0.6894 0.8124 0.067 Uiso 1 1 calc R . . C5 C 0.3706(3) 0.3089(7) 1.02571(14) 0.0623(10) Uani 1 1 d . . . H5 H 0.4308 0.2728 1.0062 0.075 Uiso 1 1 calc R . . C12 C -0.1879(3) 1.0329(6) 0.76986(13) 0.0540(9) Uani 1 1 d . . . N2 N 0.0714(3) 1.1854(6) 0.86679(13) 0.0767(10) Uani 1 1 d . . . C4 C 0.3677(3) 0.1895(7) 1.07249(16) 0.0669(10) Uani 1 1 d . . . C2 C 0.1971(4) 0.4240(8) 1.08506(16) 0.0791(12) Uani 1 1 d . . . H2 H 0.1399 0.4659 1.1057 0.095 Uiso 1 1 calc R . . C8 C 0.1751(4) 0.7104(7) 0.93843(16) 0.0829(13) Uani 1 1 d . . . H8 H 0.1173 0.5789 0.9263 0.099 Uiso 1 1 calc R . . C3 C 0.2817(4) 0.2457(8) 1.10202(17) 0.0813(12) Uani 1 1 d . . . H3 H 0.2802 0.1637 1.1335 0.098 Uiso 1 1 calc R . . C13 C -0.2158(4) 0.8466(7) 0.73445(16) 0.0761(12) Uani 1 1 d . . . H13 H -0.1611 0.7182 0.7351 0.091 Uiso 1 1 calc R . . C9 C 0.1995(4) 0.8341(7) 0.89043(15) 0.0786(12) Uani 1 1 d . . . H9A H 0.2614 0.9578 0.9006 0.094 Uiso 1 1 calc R . . H9B H 0.2315 0.7156 0.8685 0.094 Uiso 1 1 calc R . . C7 C 0.1247(4) 0.8435(8) 0.97680(18) 0.0966(14) Uani 1 1 d . . . H7A H 0.1774 0.9814 0.9882 0.116 Uiso 1 1 calc R . . H7B H 0.0465 0.9084 0.9601 0.116 Uiso 1 1 calc R . . C14 C -0.3213(5) 0.8421(9) 0.69818(18) 0.0957(14) Uani 1 1 d . . . H14 H -0.3371 0.7124 0.6747 0.115 Uiso 1 1 calc R . . C16 C -0.3793(5) 1.2117(9) 0.7311(2) 0.0936(14) Uani 1 1 d . . . H16 H -0.4355 1.3376 0.7303 0.112 Uiso 1 1 calc R . . C17 C -0.2730(4) 1.2171(7) 0.76788(17) 0.0852(13) Uani 1 1 d . . . H17 H -0.2586 1.3463 0.7916 0.102 Uiso 1 1 calc R . . C15 C -0.4025(4) 1.0262(10) 0.69648(18) 0.0891(13) Uani 1 1 d . . . H15 H -0.4738 1.0248 0.6716 0.107 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 Cl1 0.0769(8) 0.0954(8) 0.1022(9) 0.0141(6) -0.0074(6) 0.0088(6) O1 0.0710(19) 0.0835(17) 0.0721(18) 0.0002(15) 0.0248(14) 0.0165(15) C11 0.068(3) 0.0353(18) 0.058(2) 0.0023(18) 0.0238(18) -0.0017(19) C6 0.048(2) 0.059(2) 0.056(2) -0.0022(19) 0.0053(17) -0.0027(18) C1 0.050(2) 0.070(2) 0.061(3) -0.012(2) 0.0105(19) -0.001(2) N1 0.065(2) 0.0567(18) 0.064(2) 0.0042(17) 0.0111(16) 0.0025(17) O2 0.0646(18) 0.0910(18) 0.0720(18) 0.0115(15) 0.0210(14) 0.0207(15) N3 0.087(3) 0.0469(18) 0.082(2) -0.0088(17) 0.0154(19) 0.0011(18) C10 0.069(3) 0.0403(18) 0.059(2) -0.0027(18) 0.0150(19) 0.0000(19) C5 0.049(2) 0.074(2) 0.064(3) -0.008(2) 0.0096(18) -0.003(2) C12 0.061(3) 0.0472(19) 0.058(2) 0.0081(19) 0.0229(18) 0.0050(19) N2 0.090(3) 0.055(2) 0.083(2) -0.0110(19) 0.013(2) -0.0065(19) C4 0.056(3) 0.071(2) 0.067(3) 0.000(2) -0.008(2) -0.004(2) C2 0.072(3) 0.102(3) 0.066(3) -0.001(2) 0.020(2) 0.010(3) C8 0.094(4) 0.088(3) 0.070(3) 0.006(2) 0.022(2) 0.035(3) C3 0.072(3) 0.102(3) 0.070(3) 0.009(2) 0.012(2) -0.007(3) C13 0.072(3) 0.065(2) 0.089(3) -0.014(2) 0.009(2) 0.009(2) C9 0.069(3) 0.092(3) 0.075(3) 0.009(2) 0.013(2) -0.003(2) C7 0.099(4) 0.111(3) 0.083(3) 0.016(3) 0.026(3) 0.025(3) C14 0.088(4) 0.091(3) 0.099(4) -0.019(3) -0.005(3) 0.002(3) C16 0.089(4) 0.088(3) 0.105(4) 0.015(3) 0.019(3) 0.030(3) C17 0.094(4) 0.072(3) 0.088(3) -0.008(2) 0.012(3) 0.017(3) C15 0.070(3) 0.104(4) 0.090(4) 0.015(3) 0.008(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 Cl1 C4 1.740(4) . ? O1 C1 1.366(4) . ? O1 C7 1.402(4) . ? C11 C10 1.356(4) . ? C11 N3 1.365(4) . ? C11 C12 1.457(5) . ? C6 C5 1.368(4) . ? C6 O2 1.376(4) . ? C6 C1 1.382(5) . ? C1 C2 1.375(5) . ? N1 C10 1.332(4) . ? N1 N2 1.338(4) . ? N1 C9 1.448(4) . ? O2 C8 1.438(4) . ? N3 N2 1.314(4) . ? C10 H10 0.9300 . ? C5 C4 1.377(5) . ? C5 H5 0.9300 . ? C12 C13 1.367(5) . ? C12 C17 1.381(5) . ? C4 C3 1.364(5) . ? C2 C3 1.374(5) . ? C2 H2 0.9300 . ? C8 C7 1.423(5) . ? C8 C9 1.478(5) . ? C8 H8 0.9800 . ? C3 H3 0.9300 . ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C14 C15 1.351(6) . ? C14 H14 0.9300 . ? C16 C15 1.347(6) . ? C16 C17 1.381(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C15 H15 0.9300 . ? 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 C1 O1 C7 114.4(3) . . ? C10 C11 N3 107.1(3) . . ? C10 C11 C12 130.6(3) . . ? N3 C11 C12 122.3(3) . . ? C5 C6 O2 117.9(3) . . ? C5 C6 C1 120.6(4) . . ? O2 C6 C1 121.5(3) . . ? O1 C1 C2 118.5(3) . . ? O1 C1 C6 122.3(3) . . ? C2 C1 C6 119.2(4) . . ? C10 N1 N2 110.8(3) . . ? C10 N1 C9 129.5(3) . . ? N2 N1 C9 119.7(3) . . ? C6 O2 C8 113.0(3) . . ? N2 N3 C11 109.3(3) . . ? N1 C10 C11 106.1(3) . . ? N1 C10 H10 126.9 . . ? C11 C10 H10 126.9 . . ? C6 C5 C4 119.3(4) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C13 C12 C17 116.5(4) . . ? C13 C12 C11 121.2(3) . . ? C17 C12 C11 122.3(4) . . ? N3 N2 N1 106.7(3) . . ? C3 C4 C5 120.7(4) . . ? C3 C4 Cl1 119.8(3) . . ? C5 C4 Cl1 119.5(3) . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C7 C8 O2 112.2(4) . . ? C7 C8 C9 120.2(4) . . ? O2 C8 C9 105.0(3) . . ? C7 C8 H8 106.2 . . ? O2 C8 H8 106.2 . . ? C9 C8 H8 106.2 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C12 C13 C14 122.4(4) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? N1 C9 C8 113.2(3) . . ? N1 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O1 C7 C8 115.6(4) . . ? O1 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? O1 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.4 . . ? C15 C14 C13 120.0(5) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C16 C17 120.7(4) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.8(4) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C16 C15 C14 119.5(5) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.379 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 929370' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compd-20 #TrackingRef 'kckcif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N4 O3 S' _chemical_formula_weight 450.55 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+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5356(5) _cell_length_b 10.9149(6) _cell_length_c 24.3049(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.720(6) _cell_angle_gamma 90.00 _cell_volume 2253.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2286 _cell_measurement_theta_min 2.7844 _cell_measurement_theta_max 28.9534 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91090 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7812 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3948 _reflns_number_gt 2944 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+0.9443P] 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 3948 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1956 _refine_ls_wR_factor_gt 0.1784 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.74125(9) 1.18424(8) 0.20589(4) 0.0531(3) Uani 1 1 d . . . O1 O 0.2831(2) 1.04020(19) 0.17326(9) 0.0516(6) Uani 1 1 d . . . N1 N 0.5588(3) 1.1624(2) 0.22237(10) 0.0445(6) Uani 1 1 d . . . C1 C 0.2981(4) 1.1646(3) 0.17096(12) 0.0431(7) Uani 1 1 d . . . N2 N 0.2794(3) 0.7859(2) 0.15964(10) 0.0458(6) Uani 1 1 d . . . C6 C 0.4305(3) 1.2288(3) 0.19351(12) 0.0431(7) Uani 1 1 d . . . O3 O 0.8401(3) 1.1104(2) 0.24319(10) 0.0698(7) Uani 1 1 d . . . C8 C 0.4245(3) 0.9737(3) 0.18814(12) 0.0438(7) Uani 1 1 d . . . H8 H 0.4871 0.9711 0.1565 0.053 Uiso 1 1 calc R . . C11 C 0.0882(4) 0.7049(3) 0.10834(13) 0.0450(7) Uani 1 1 d . . . N4 N 0.2193(3) 0.7045(3) 0.08106(12) 0.0606(8) Uani 1 1 d . . . C9 C 0.3813(4) 0.8459(3) 0.20308(13) 0.0540(8) Uani 1 1 d . . . H9A H 0.4767 0.7980 0.2107 0.065 Uiso 1 1 calc R . . H9B H 0.3283 0.8482 0.2366 0.065 Uiso 1 1 calc R . . O2 O 0.7654(3) 1.3127(2) 0.20467(11) 0.0701(7) Uani 1 1 d . . . C5 C 0.4293(4) 1.3558(3) 0.19072(13) 0.0530(8) Uani 1 1 d . . . H5 H 0.5152 1.3997 0.2068 0.064 Uiso 1 1 calc R . . C7 C 0.5184(4) 1.0366(3) 0.23614(12) 0.0479(7) Uani 1 1 d . . . H7A H 0.4575 1.0373 0.2678 0.057 Uiso 1 1 calc R . . H7B H 0.6143 0.9907 0.2463 0.057 Uiso 1 1 calc R . . C2 C 0.1699(4) 1.2280(3) 0.14556(14) 0.0560(8) Uani 1 1 d . . . H2 H 0.0814 1.1851 0.1308 0.067 Uiso 1 1 calc R . . C18 C 0.7480(3) 1.1272(3) 0.13864(13) 0.0480(8) Uani 1 1 d . . . N3 N 0.3351(3) 0.7542(3) 0.11222(12) 0.0613(8) Uani 1 1 d . . . C4 C 0.3030(5) 1.4174(3) 0.16451(16) 0.0647(10) Uani 1 1 d . . . H4 H 0.3055 1.5024 0.1619 0.078 Uiso 1 1 calc R . . C10 C 0.1282(4) 0.7564(3) 0.15850(13) 0.0473(7) Uani 1 1 d . . . H10 H 0.0629 0.7686 0.1864 0.057 Uiso 1 1 calc R . . C19 C 0.6904(5) 1.1966(3) 0.09392(16) 0.0685(11) Uani 1 1 d . . . H19 H 0.6491 1.2740 0.0992 0.082 Uiso 1 1 calc R . . C3 C 0.1722(5) 1.3535(3) 0.14193(15) 0.0648(10) Uani 1 1 d . . . H3 H 0.0863 1.3953 0.1244 0.078 Uiso 1 1 calc R . . C12 C -0.0637(4) 0.6565(3) 0.08445(14) 0.0525(8) Uani 1 1 d . . . C23 C 0.8068(5) 1.0127(3) 0.13096(15) 0.0644(10) Uani 1 1 d . . . H23 H 0.8454 0.9653 0.1611 0.077 Uiso 1 1 calc R . . C17 C -0.1826(4) 0.6330(4) 0.12155(16) 0.0709(10) Uani 1 1 d . . . H17A H -0.2085 0.7100 0.1384 0.085 Uiso 1 1 calc R . . H17B H -0.1373 0.5798 0.1509 0.085 Uiso 1 1 calc R . . C21 C 0.7512(5) 1.0346(4) 0.03270(16) 0.0702(10) Uani 1 1 d . . . C22 C 0.8082(5) 0.9686(3) 0.07800(17) 0.0764(12) Uani 1 1 d . . . H22 H 0.8495 0.8910 0.0729 0.092 Uiso 1 1 calc R . . C20 C 0.6941(6) 1.1511(4) 0.04169(16) 0.0808(12) Uani 1 1 d . . . H20 H 0.6576 1.1993 0.0115 0.097 Uiso 1 1 calc R . . C13 C -0.0943(5) 0.6388(4) 0.02818(16) 0.0748(11) Uani 1 1 d . . . H13 H -0.0144 0.6519 0.0055 0.090 Uiso 1 1 calc R . . C24 C 0.7545(7) 0.9855(5) -0.02502(19) 0.1103(18) Uani 1 1 d . . . H24A H 0.7445 0.8979 -0.0245 0.165 Uiso 1 1 calc R . . H24B H 0.8524 1.0073 -0.0387 0.165 Uiso 1 1 calc R . . H24C H 0.6688 1.0199 -0.0486 0.165 Uiso 1 1 calc R . . C16 C -0.3326(5) 0.5756(5) 0.0963(3) 0.1070(18) Uani 1 1 d . . . H16A H -0.3188 0.4875 0.0949 0.128 Uiso 1 1 calc R . . H16B H -0.4158 0.5924 0.1197 0.128 Uiso 1 1 calc R . . C15 C -0.3804(7) 0.6213(8) 0.0404(3) 0.143(3) Uani 1 1 d . . . H15A H -0.4023 0.7083 0.0419 0.171 Uiso 1 1 calc R . . H15B H -0.4761 0.5800 0.0255 0.171 Uiso 1 1 calc R . . C14 C -0.2528(6) 0.5991(6) 0.0031(2) 0.123(2) Uani 1 1 d . . . H14A H -0.2494 0.5124 -0.0056 0.147 Uiso 1 1 calc R . . H14B H -0.2784 0.6431 -0.0314 0.147 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 0.0482(5) 0.0524(5) 0.0570(5) -0.0065(4) -0.0029(4) -0.0066(4) O1 0.0515(12) 0.0462(12) 0.0549(13) -0.0001(10) -0.0047(10) 0.0000(10) N1 0.0523(15) 0.0415(13) 0.0390(13) -0.0003(10) 0.0007(11) -0.0001(11) C1 0.0523(18) 0.0441(17) 0.0339(15) 0.0004(12) 0.0091(13) 0.0020(14) N2 0.0585(16) 0.0372(13) 0.0417(14) 0.0003(11) 0.0044(12) 0.0011(12) C6 0.0507(18) 0.0440(17) 0.0361(15) 0.0005(12) 0.0118(13) 0.0009(14) O3 0.0536(14) 0.0859(18) 0.0654(16) -0.0023(13) -0.0168(12) 0.0042(13) C8 0.0499(17) 0.0426(17) 0.0379(16) 0.0012(12) -0.0002(13) 0.0004(13) C11 0.0513(18) 0.0377(16) 0.0463(17) 0.0049(13) 0.0072(14) -0.0005(13) N4 0.0599(17) 0.0692(19) 0.0542(17) -0.0153(14) 0.0139(14) -0.0135(15) C9 0.067(2) 0.0476(18) 0.0445(18) 0.0016(14) -0.0080(15) -0.0039(16) O2 0.0641(15) 0.0564(15) 0.090(2) -0.0178(13) 0.0087(14) -0.0193(12) C5 0.060(2) 0.0471(18) 0.054(2) 0.0000(15) 0.0148(16) 0.0007(16) C7 0.0578(19) 0.0460(17) 0.0385(16) 0.0023(13) -0.0023(14) -0.0009(15) C2 0.0503(18) 0.066(2) 0.0519(19) 0.0044(16) 0.0042(15) 0.0074(17) C18 0.0433(16) 0.0474(18) 0.0541(19) 0.0045(14) 0.0093(14) -0.0018(14) N3 0.0577(17) 0.0679(19) 0.0602(18) -0.0139(15) 0.0150(14) -0.0104(15) C4 0.076(2) 0.050(2) 0.072(2) 0.0118(17) 0.024(2) 0.0123(19) C10 0.0542(19) 0.0449(17) 0.0438(17) 0.0044(13) 0.0101(14) 0.0006(14) C19 0.092(3) 0.051(2) 0.065(2) 0.0106(17) 0.023(2) 0.0190(19) C3 0.069(2) 0.067(2) 0.060(2) 0.0143(18) 0.0131(18) 0.022(2) C12 0.0529(19) 0.0414(17) 0.063(2) 0.0017(15) 0.0044(16) -0.0016(14) C23 0.083(3) 0.050(2) 0.060(2) 0.0025(16) 0.0038(19) 0.0162(18) C17 0.069(2) 0.080(3) 0.065(2) 0.019(2) 0.0101(19) -0.007(2) C21 0.091(3) 0.064(2) 0.059(2) -0.0023(18) 0.023(2) 0.002(2) C22 0.106(3) 0.050(2) 0.075(3) -0.0030(19) 0.017(2) 0.019(2) C20 0.115(3) 0.080(3) 0.051(2) 0.0170(19) 0.025(2) 0.027(2) C13 0.071(2) 0.095(3) 0.059(2) -0.028(2) 0.0083(19) -0.016(2) C24 0.166(5) 0.103(4) 0.066(3) -0.009(2) 0.032(3) 0.017(4) C16 0.057(3) 0.105(4) 0.159(5) 0.041(4) 0.011(3) -0.014(2) C15 0.086(4) 0.204(7) 0.136(6) -0.068(5) 0.000(4) -0.035(4) C14 0.082(3) 0.183(6) 0.102(4) -0.065(4) 0.006(3) -0.038(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.418(2) . ? S1 O3 1.425(3) . ? S1 N1 1.663(3) . ? S1 C18 1.755(3) . ? O1 C1 1.366(4) . ? O1 C8 1.423(3) . ? N1 C6 1.437(4) . ? N1 C7 1.463(4) . ? C1 C2 1.387(4) . ? C1 C6 1.394(4) . ? N2 C10 1.328(4) . ? N2 N3 1.335(4) . ? N2 C9 1.455(4) . ? C6 C5 1.387(4) . ? C8 C9 1.497(4) . ? C8 C7 1.513(4) . ? C8 H8 0.9800 . ? C11 C10 1.355(4) . ? C11 N4 1.356(4) . ? C11 C12 1.465(4) . ? N4 N3 1.303(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C5 C4 1.372(5) . ? C5 H5 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C2 C3 1.373(5) . ? C2 H2 0.9300 . ? C18 C23 1.367(5) . ? C18 C19 1.374(5) . ? C4 C3 1.383(5) . ? C4 H4 0.9300 . ? C10 H10 0.9300 . ? C19 C20 1.366(5) . ? C19 H19 0.9300 . ? C3 H3 0.9300 . ? C12 C13 1.380(5) . ? C12 C17 1.446(5) . ? C23 C22 1.376(5) . ? C23 H23 0.9300 . ? C17 C16 1.500(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C21 C22 1.365(5) . ? C21 C20 1.387(6) . ? C21 C24 1.505(5) . ? C22 H22 0.9300 . ? C20 H20 0.9300 . ? C13 C14 1.493(6) . ? C13 H13 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C16 C15 1.468(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C15 C14 1.504(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 119.63(16) . . ? O2 S1 N1 106.78(14) . . ? O3 S1 N1 105.96(14) . . ? O2 S1 C18 108.21(16) . . ? O3 S1 C18 108.64(16) . . ? N1 S1 C18 106.95(13) . . ? C1 O1 C8 115.9(2) . . ? C6 N1 C7 113.6(2) . . ? C6 N1 S1 119.78(19) . . ? C7 N1 S1 115.9(2) . . ? O1 C1 C2 116.2(3) . . ? O1 C1 C6 124.0(3) . . ? C2 C1 C6 119.8(3) . . ? C10 N2 N3 110.4(3) . . ? C10 N2 C9 129.3(3) . . ? N3 N2 C9 120.3(3) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 N1 122.0(3) . . ? C1 C6 N1 119.1(3) . . ? O1 C8 C9 108.3(2) . . ? O1 C8 C7 109.6(2) . . ? C9 C8 C7 111.1(2) . . ? O1 C8 H8 109.3 . . ? C9 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? C10 C11 N4 107.2(3) . . ? C10 C11 C12 129.8(3) . . ? N4 C11 C12 123.1(3) . . ? N3 N4 C11 109.3(3) . . ? N2 C9 C8 112.8(2) . . ? N2 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? N2 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? N1 C7 C8 111.6(2) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C23 C18 C19 120.2(3) . . ? C23 C18 S1 119.9(3) . . ? C19 C18 S1 119.9(3) . . ? N4 N3 N2 107.1(3) . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N2 C10 C11 106.1(3) . . ? N2 C10 H10 127.0 . . ? C11 C10 H10 127.0 . . ? C20 C19 C18 119.7(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C2 C3 C4 119.6(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C13 C12 C17 121.2(3) . . ? C13 C12 C11 121.0(3) . . ? C17 C12 C11 117.7(3) . . ? C18 C23 C22 119.1(3) . . ? C18 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C12 C17 C16 116.2(4) . . ? C12 C17 H17A 108.2 . . ? C16 C17 H17A 108.2 . . ? C12 C17 H17B 108.2 . . ? C16 C17 H17B 108.2 . . ? H17A C17 H17B 107.4 . . ? C22 C21 C20 117.4(4) . . ? C22 C21 C24 121.7(4) . . ? C20 C21 C24 120.9(4) . . ? C21 C22 C23 122.3(3) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C19 C20 C21 121.4(4) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C12 C13 C14 121.4(4) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C15 C16 C17 112.6(4) . . ? C15 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? C15 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.8 . . ? C16 C15 C14 110.7(6) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C13 C14 C15 112.8(4) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.781 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 929371' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compd-30 #TrackingRef 'kckcif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N4 O4' _chemical_formula_weight 352.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0255(6) _cell_length_b 10.3665(11) _cell_length_c 13.6263(14) _cell_angle_alpha 92.903(9) _cell_angle_beta 97.168(8) _cell_angle_gamma 94.666(8) _cell_volume 840.11(15) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1486 _cell_measurement_theta_min 3.0130 _cell_measurement_theta_max 29.0884 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83383 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5225 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2948 _reflns_number_gt 2051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0741P)^2^+0.0486P] 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 2948 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1525 _refine_ls_wR_factor_gt 0.1378 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3818(2) 0.33113(15) 0.84987(12) 0.0578(5) Uani 1 1 d . . . O2 O 0.8667(2) 0.36683(15) 0.94288(12) 0.0595(5) Uani 1 1 d . . . N3 N 0.0459(3) -0.10775(19) 0.86069(17) 0.0679(6) Uani 1 1 d . . . N2 N 0.2035(3) -0.0400(2) 0.92149(18) 0.0712(7) Uani 1 1 d . . . C1 C 0.4862(4) 0.3591(2) 0.76785(18) 0.0524(6) Uani 1 1 d . . . C12 C -0.0809(3) -0.0250(2) 0.80883(17) 0.0489(6) Uani 1 1 d . . . C6 C 0.7015(4) 0.4222(2) 0.77834(19) 0.0536(6) Uani 1 1 d . . . N1 N 0.1759(3) 0.08571(18) 0.91038(15) 0.0562(5) Uani 1 1 d . . . C13 C -0.2810(3) -0.0727(2) 0.74085(17) 0.0496(6) Uani 1 1 d . . . C11 C 0.0034(3) 0.0978(2) 0.84035(18) 0.0557(6) Uani 1 1 d . . . H11 H -0.0483 0.1746 0.8179 0.067 Uiso 1 1 calc R . . C14 C -0.3624(4) -0.2018(2) 0.73777(19) 0.0638(7) Uani 1 1 d . . . H14 H -0.2821 -0.2590 0.7754 0.077 Uiso 1 1 calc R . . C8 C 0.6779(4) 0.3272(2) 0.98927(18) 0.0559(6) Uani 1 1 d . . . H8A H 0.6175 0.4032 1.0163 0.067 Uiso 1 1 calc R . . H8B H 0.7248 0.2749 1.0439 0.067 Uiso 1 1 calc R . . C9 C 0.4955(3) 0.2497(2) 0.91881(18) 0.0529(6) Uani 1 1 d . . . H9 H 0.5632 0.1832 0.8816 0.063 Uiso 1 1 calc R . . C7 C 0.8275(4) 0.4671(2) 0.87748(19) 0.0594(7) Uani 1 1 d . . . H7A H 0.9710 0.5106 0.8676 0.071 Uiso 1 1 calc R . . H7B H 0.7440 0.5302 0.9086 0.071 Uiso 1 1 calc R . . C10 C 0.3219(4) 0.1851(2) 0.97356(19) 0.0605(7) Uani 1 1 d . . . H10A H 0.3956 0.1454 1.0303 0.073 Uiso 1 1 calc R . . H10B H 0.2311 0.2498 0.9979 0.073 Uiso 1 1 calc R . . C16 C -0.6735(4) -0.1622(3) 0.6246(2) 0.0640(7) Uani 1 1 d . . . C5 C 0.7912(4) 0.4490(2) 0.6926(2) 0.0661(7) Uani 1 1 d . . . H5 H 0.9358 0.4897 0.6972 0.079 Uiso 1 1 calc R . . C15 C -0.5596(4) -0.2471(3) 0.6801(2) 0.0704(7) Uani 1 1 d . . . H15 H -0.6141 -0.3337 0.6791 0.084 Uiso 1 1 calc R . . C2 C 0.3676(4) 0.3274(2) 0.6749(2) 0.0621(7) Uani 1 1 d . . . H2 H 0.2233 0.2862 0.6691 0.074 Uiso 1 1 calc R . . O3 O -0.9731(4) -0.3145(3) 0.57828(19) 0.1117(8) Uani 1 1 d . . . C18 C -0.3986(4) 0.0098(2) 0.6822(2) 0.0663(7) Uani 1 1 d . . . H18 H -0.3442 0.0964 0.6822 0.080 Uiso 1 1 calc R . . N4 N -0.8864(4) -0.2092(3) 0.5639(2) 0.0879(8) Uani 1 1 d . . . C17 C -0.5958(4) -0.0344(3) 0.6238(2) 0.0752(8) Uani 1 1 d . . . H17 H -0.6750 0.0215 0.5844 0.090 Uiso 1 1 calc R . . C3 C 0.4601(5) 0.3561(3) 0.5934(2) 0.0719(8) Uani 1 1 d . . . H3 H 0.3795 0.3345 0.5311 0.086 Uiso 1 1 calc R . . C4 C 0.6735(5) 0.4173(3) 0.6010(2) 0.0781(8) Uani 1 1 d . . . H4 H 0.7371 0.4370 0.5442 0.094 Uiso 1 1 calc R . . O4 O -0.9614(5) -0.1414(3) 0.5012(3) 0.1479(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0403(8) 0.0645(11) 0.0656(11) 0.0080(9) -0.0042(7) 0.0024(7) O2 0.0438(9) 0.0549(10) 0.0741(12) -0.0011(9) -0.0089(8) -0.0002(7) N3 0.0595(12) 0.0482(12) 0.0899(17) 0.0122(11) -0.0151(11) 0.0006(10) N2 0.0596(13) 0.0530(13) 0.0951(18) 0.0194(12) -0.0158(12) -0.0001(10) C1 0.0465(12) 0.0472(13) 0.0613(16) 0.0072(12) -0.0019(11) 0.0025(10) C12 0.0396(11) 0.0444(13) 0.0622(15) 0.0067(11) 0.0041(10) 0.0016(10) C6 0.0464(12) 0.0438(13) 0.0673(17) 0.0029(12) -0.0031(11) 0.0005(10) N1 0.0446(10) 0.0495(11) 0.0710(14) 0.0076(10) -0.0032(10) -0.0015(8) C13 0.0458(12) 0.0463(13) 0.0559(15) 0.0014(11) 0.0057(10) 0.0014(10) C11 0.0424(12) 0.0489(14) 0.0732(17) 0.0102(12) -0.0054(11) 0.0030(10) C14 0.0665(15) 0.0490(14) 0.0707(18) 0.0084(13) -0.0075(13) -0.0036(12) C8 0.0526(13) 0.0474(13) 0.0624(16) 0.0015(12) -0.0098(11) 0.0010(11) C9 0.0437(12) 0.0516(13) 0.0599(15) 0.0033(11) -0.0053(11) 0.0016(10) C7 0.0516(13) 0.0493(14) 0.0719(17) 0.0010(13) -0.0047(12) -0.0070(11) C10 0.0490(13) 0.0634(16) 0.0656(16) -0.0035(13) 0.0005(12) -0.0013(12) C16 0.0559(14) 0.0626(16) 0.0675(17) -0.0095(13) -0.0029(12) -0.0059(12) C5 0.0604(15) 0.0578(16) 0.078(2) 0.0052(14) 0.0063(14) -0.0031(12) C15 0.0759(17) 0.0555(15) 0.0738(19) 0.0013(14) 0.0000(14) -0.0141(13) C2 0.0487(13) 0.0618(15) 0.0681(18) 0.0029(14) -0.0153(13) -0.0056(11) O3 0.0883(14) 0.1142(19) 0.1164(19) -0.0019(16) -0.0113(13) -0.0455(14) C18 0.0633(15) 0.0469(14) 0.0826(19) 0.0038(13) -0.0102(13) -0.0025(12) N4 0.0733(16) 0.0792(18) 0.100(2) -0.0099(16) -0.0161(15) -0.0088(15) C17 0.0676(16) 0.0631(17) 0.087(2) 0.0043(15) -0.0211(14) 0.0059(14) C3 0.0803(18) 0.0663(17) 0.0615(18) 0.0090(14) -0.0172(14) -0.0012(14) C4 0.087(2) 0.078(2) 0.069(2) 0.0150(16) 0.0099(16) 0.0010(16) O4 0.123(2) 0.1017(19) 0.189(3) 0.0147(19) -0.089(2) -0.0117(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.381(3) . ? O1 C9 1.442(2) . ? O2 C8 1.412(3) . ? O2 C7 1.418(3) . ? N3 N2 1.310(3) . ? N3 C12 1.362(3) . ? N2 N1 1.341(3) . ? C1 C2 1.384(3) . ? C1 C6 1.392(3) . ? C12 C11 1.359(3) . ? C12 C13 1.461(3) . ? C6 C5 1.378(4) . ? C6 C7 1.497(3) . ? N1 C11 1.339(3) . ? N1 C10 1.466(3) . ? C13 C18 1.378(3) . ? C13 C14 1.384(3) . ? C11 H11 0.9300 . ? C14 C15 1.374(3) . ? C14 H14 0.9300 . ? C8 C9 1.513(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.493(3) . ? C9 H9 0.9800 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C16 C15 1.361(3) . ? C16 C17 1.370(4) . ? C16 N4 1.469(3) . ? C5 C4 1.367(4) . ? C5 H5 0.9300 . ? C15 H15 0.9300 . ? C2 C3 1.340(4) . ? C2 H2 0.9300 . ? O3 N4 1.207(3) . ? C18 C17 1.376(3) . ? C18 H18 0.9300 . ? N4 O4 1.202(3) . ? C17 H17 0.9300 . ? C3 C4 1.376(4) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? 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 C1 O1 C9 116.10(16) . . ? C8 O2 C7 113.34(17) . . ? N2 N3 C12 108.95(19) . . ? N3 N2 N1 107.45(17) . . ? O1 C1 C2 118.2(2) . . ? O1 C1 C6 120.9(2) . . ? C2 C1 C6 120.9(2) . . ? C11 C12 N3 107.50(19) . . ? C11 C12 C13 130.94(19) . . ? N3 C12 C13 121.3(2) . . ? C5 C6 C1 117.1(2) . . ? C5 C6 C7 120.5(2) . . ? C1 C6 C7 122.3(2) . . ? C11 N1 N2 110.1(2) . . ? C11 N1 C10 130.2(2) . . ? N2 N1 C10 119.67(19) . . ? C18 C13 C14 118.6(2) . . ? C18 C13 C12 121.3(2) . . ? C14 C13 C12 120.1(2) . . ? N1 C11 C12 105.99(19) . . ? N1 C11 H11 127.0 . . ? C12 C11 H11 127.0 . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? O2 C8 C9 112.5(2) . . ? O2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? O2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O1 C9 C10 107.21(17) . . ? O1 C9 C8 111.49(17) . . ? C10 C9 C8 111.2(2) . . ? O1 C9 H9 109.0 . . ? C10 C9 H9 109.0 . . ? C8 C9 H9 109.0 . . ? O2 C7 C6 114.54(19) . . ? O2 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? O2 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N1 C10 C9 111.7(2) . . ? N1 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N1 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C15 C16 C17 121.9(2) . . ? C15 C16 N4 119.0(2) . . ? C17 C16 N4 119.1(2) . . ? C4 C5 C6 121.8(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C16 C15 C14 118.5(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C3 C2 C1 120.2(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C17 C18 C13 120.7(2) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? O4 N4 O3 123.8(3) . . ? O4 N4 C16 117.8(3) . . ? O3 N4 C16 118.4(3) . . ? C16 C17 C18 118.9(2) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.331 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 929372' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compd-32 #TrackingRef 'kckcif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 N4 O3 S' _chemical_formula_weight 384.45 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)/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 8.4958(6) _cell_length_b 11.6503(8) _cell_length_c 18.9628(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.1160(10) _cell_angle_gamma 90.00 _cell_volume 1872.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9740 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADABS, Sheldrick (1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18997 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3694 _reflns_number_gt 2931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0805P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3694 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.16956(5) 0.18239(4) 0.46216(2) 0.04549(17) Uani 1 1 d . . . O3 O 0.39090(16) 0.21696(12) 0.58989(6) 0.0552(4) Uani 1 1 d . . . H3 H 0.4208 0.2541 0.6251 0.083 Uiso 1 1 calc R . . O1 O 0.11834(16) 0.17799(12) 0.38901(7) 0.0613(4) Uani 1 1 d . . . N1 N 0.52927(18) -0.17687(13) 0.78588(8) 0.0488(4) Uani 1 1 d . . . C6 C 0.4419(2) 0.26799(14) 0.53164(9) 0.0416(4) Uani 1 1 d . . . C7 C 0.18989(19) 0.01956(15) 0.55880(8) 0.0416(4) Uani 1 1 d . . . H7 H 0.1448 0.0728 0.5878 0.050 Uiso 1 1 calc R . . O2 O 0.07316(15) 0.23390(12) 0.51148(8) 0.0608(4) Uani 1 1 d . . . C5 C 0.5785(2) 0.33262(14) 0.53315(10) 0.0453(4) Uani 1 1 d . . . H5 H 0.6358 0.3450 0.5761 0.054 Uiso 1 1 calc R . . C18 C 0.6012(2) -0.08731(15) 0.75576(8) 0.0417(4) Uani 1 1 d . . . C1 C 0.3548(2) 0.25070(14) 0.46709(9) 0.0414(4) Uani 1 1 d . . . C4 C 0.6322(2) 0.37946(15) 0.47197(10) 0.0479(4) Uani 1 1 d . . . C2 C 0.4101(2) 0.29625(15) 0.40540(10) 0.0492(4) Uani 1 1 d . . . H2 H 0.3542 0.2835 0.3621 0.059 Uiso 1 1 calc R . . C10 C 0.7648(2) -0.05481(15) 0.77724(9) 0.0431(4) Uani 1 1 d . . . C8 C 0.2413(2) -0.07736(16) 0.58829(9) 0.0478(4) Uani 1 1 d . . . H8 H 0.2943 -0.1300 0.5617 0.057 Uiso 1 1 calc R . . C9 C 0.2159(2) -0.1035(2) 0.66273(10) 0.0598(5) Uani 1 1 d . . . H9A H 0.1613 -0.1764 0.6651 0.072 Uiso 1 1 calc R . . H9B H 0.1491 -0.0448 0.6812 0.072 Uiso 1 1 calc R . . C11 C 0.8215(2) 0.05405(16) 0.76481(10) 0.0537(5) Uani 1 1 d . . . H11 H 0.7562 0.1079 0.7412 0.064 Uiso 1 1 calc R . . C15 C 0.8664(2) -0.13412(18) 0.81163(10) 0.0542(5) Uani 1 1 d . . . H15 H 0.8312 -0.2081 0.8199 0.065 Uiso 1 1 calc R . . C3 C 0.5463(2) 0.35962(16) 0.40829(10) 0.0510(5) Uani 1 1 d . . . H3A H 0.5816 0.3898 0.3668 0.061 Uiso 1 1 calc R . . C16 C 0.2671(3) -0.03112(18) 0.44052(10) 0.0604(5) Uani 1 1 d . . . H16A H 0.3789 -0.0353 0.4519 0.091 Uiso 1 1 calc R . . H16B H 0.2472 -0.0051 0.3927 0.091 Uiso 1 1 calc R . . H16C H 0.2213 -0.1058 0.4455 0.091 Uiso 1 1 calc R . . C17 C 0.7820(2) 0.44884(18) 0.47535(12) 0.0641(6) Uani 1 1 d . . . H17A H 0.7832 0.4963 0.4340 0.096 Uiso 1 1 calc R . . H17B H 0.8712 0.3981 0.4774 0.096 Uiso 1 1 calc R . . H17C H 0.7871 0.4964 0.5168 0.096 Uiso 1 1 calc R . . C12 C 0.9749(3) 0.08331(19) 0.78726(12) 0.0664(6) Uani 1 1 d . . . H12 H 1.0120 0.1568 0.7788 0.080 Uiso 1 1 calc R . . C14 C 1.0184(2) -0.1034(2) 0.83334(12) 0.0677(6) Uani 1 1 d . . . H14 H 1.0851 -0.1572 0.8561 0.081 Uiso 1 1 calc R . . C13 C 1.0729(3) 0.0043(2) 0.82204(12) 0.0717(6) Uani 1 1 d . . . H13 H 1.1754 0.0245 0.8377 0.086 Uiso 1 1 calc R . . N3 N 0.38576(19) -0.18985(14) 0.75645(8) 0.0551(4) Uani 1 1 d . . . N2 N 0.36551(17) -0.10926(13) 0.70722(8) 0.0479(4) Uani 1 1 d . . . C19 C 0.4940(2) -0.04277(16) 0.70562(9) 0.0483(4) Uani 1 1 d . . . H19 H 0.5075 0.0203 0.6766 0.058 Uiso 1 1 calc R . . N4 N 0.19747(17) 0.04878(12) 0.48816(7) 0.0427(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0390(3) 0.0472(3) 0.0485(3) 0.00581(19) -0.0091(2) 0.00168(18) O3 0.0640(9) 0.0653(8) 0.0357(7) -0.0084(6) -0.0002(6) -0.0202(7) O1 0.0574(8) 0.0693(9) 0.0530(8) 0.0172(7) -0.0240(7) -0.0115(7) N1 0.0483(9) 0.0553(9) 0.0408(8) 0.0101(7) -0.0103(7) -0.0041(7) C6 0.0451(10) 0.0411(9) 0.0382(9) -0.0028(7) 0.0005(7) 0.0019(7) C7 0.0357(8) 0.0529(10) 0.0350(9) -0.0020(7) -0.0048(7) -0.0019(7) O2 0.0456(7) 0.0559(8) 0.0809(10) 0.0012(7) 0.0040(7) 0.0109(6) C5 0.0454(10) 0.0431(10) 0.0463(10) -0.0045(8) -0.0046(8) -0.0016(8) C18 0.0455(10) 0.0465(10) 0.0326(9) 0.0005(7) -0.0001(7) 0.0023(7) C1 0.0408(9) 0.0395(9) 0.0427(10) -0.0005(7) -0.0043(7) 0.0020(7) C4 0.0459(10) 0.0378(9) 0.0598(12) 0.0008(8) 0.0029(9) 0.0031(7) C2 0.0558(11) 0.0492(10) 0.0414(10) 0.0049(8) -0.0056(8) 0.0027(8) C10 0.0437(10) 0.0505(10) 0.0348(9) -0.0057(7) 0.0009(7) 0.0012(8) C8 0.0452(10) 0.0560(11) 0.0409(10) 0.0039(8) -0.0061(8) 0.0008(8) C9 0.0429(10) 0.0870(15) 0.0473(11) 0.0195(10) -0.0115(8) -0.0062(10) C11 0.0569(12) 0.0517(11) 0.0524(11) -0.0040(9) 0.0035(9) 0.0011(9) C15 0.0484(11) 0.0591(12) 0.0544(12) 0.0018(9) -0.0017(9) 0.0005(9) C3 0.0565(11) 0.0495(10) 0.0475(11) 0.0075(8) 0.0064(9) -0.0005(9) C16 0.0787(14) 0.0588(12) 0.0442(11) -0.0034(9) 0.0072(10) 0.0093(10) C17 0.0542(12) 0.0619(13) 0.0763(15) 0.0050(11) 0.0046(10) -0.0115(10) C12 0.0654(14) 0.0625(13) 0.0723(14) -0.0141(11) 0.0107(11) -0.0186(11) C14 0.0472(12) 0.0878(16) 0.0665(14) 0.0042(12) -0.0076(10) 0.0058(11) C13 0.0471(12) 0.0979(17) 0.0691(15) -0.0120(13) -0.0039(10) -0.0127(12) N3 0.0542(10) 0.0649(10) 0.0441(9) 0.0160(7) -0.0099(7) -0.0087(7) N2 0.0436(8) 0.0610(9) 0.0380(8) 0.0129(7) -0.0055(6) -0.0025(7) C19 0.0468(10) 0.0535(11) 0.0441(10) 0.0120(8) -0.0002(8) -0.0016(8) N4 0.0478(8) 0.0447(8) 0.0348(7) 0.0012(6) -0.0018(6) 0.0009(6) _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 1.4197(14) . ? S1 O1 1.4246(13) . ? S1 N4 1.6449(14) . ? S1 C1 1.7601(18) . ? O3 C6 1.353(2) . ? O3 H3 0.8200 . ? N1 N3 1.313(2) . ? N1 C18 1.356(2) . ? C6 C5 1.382(2) . ? C6 C1 1.399(2) . ? C7 C8 1.320(2) . ? C7 N4 1.388(2) . ? C7 H7 0.9300 . ? C5 C4 1.389(3) . ? C5 H5 0.9300 . ? C18 C19 1.371(2) . ? C18 C10 1.470(2) . ? C1 C2 1.396(2) . ? C4 C3 1.385(3) . ? C4 C17 1.505(3) . ? C2 C3 1.371(3) . ? C2 H2 0.9300 . ? C10 C11 1.383(3) . ? C10 C15 1.394(3) . ? C8 C9 1.475(3) . ? C8 H8 0.9300 . ? C9 N2 1.476(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C15 C14 1.374(3) . ? C15 H15 0.9300 . ? C3 H3A 0.9300 . ? C16 N4 1.452(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C12 C13 1.377(3) . ? C12 H12 0.9300 . ? C14 C13 1.360(3) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? N3 N2 1.326(2) . ? N2 C19 1.341(2) . ? C19 H19 0.9300 . ? 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 120.42(9) . . ? O2 S1 N4 106.27(8) . . ? O1 S1 N4 106.57(8) . . ? O2 S1 C1 109.26(8) . . ? O1 S1 C1 106.11(8) . . ? N4 S1 C1 107.63(8) . . ? C6 O3 H3 109.5 . . ? N3 N1 C18 110.04(14) . . ? O3 C6 C5 122.69(15) . . ? O3 C6 C1 118.11(15) . . ? C5 C6 C1 119.16(16) . . ? C8 C7 N4 125.56(17) . . ? C8 C7 H7 117.2 . . ? N4 C7 H7 117.2 . . ? C6 C5 C4 121.52(17) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? N1 C18 C19 106.63(15) . . ? N1 C18 C10 121.84(15) . . ? C19 C18 C10 131.52(16) . . ? C2 C1 C6 119.34(16) . . ? C2 C1 S1 118.73(13) . . ? C6 C1 S1 121.75(13) . . ? C3 C4 C5 118.60(17) . . ? C3 C4 C17 121.19(18) . . ? C5 C4 C17 120.21(17) . . ? C3 C2 C1 120.34(17) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C11 C10 C15 118.43(18) . . ? C11 C10 C18 121.54(17) . . ? C15 C10 C18 120.02(16) . . ? C7 C8 C9 121.01(19) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 N2 112.15(16) . . ? C8 C9 H9A 109.2 . . ? N2 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? N2 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C10 C11 C12 120.35(19) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C2 C3 C4 121.03(17) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C17 H17A 109.5 . . ? C4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C12 C11 120.4(2) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C13 C14 C15 121.0(2) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C13 C12 119.4(2) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? N1 N3 N2 106.70(14) . . ? N3 N2 C19 111.11(14) . . ? N3 N2 C9 119.82(15) . . ? C19 N2 C9 129.07(15) . . ? N2 C19 C18 105.50(15) . . ? N2 C19 H19 127.2 . . ? C18 C19 H19 127.2 . . ? C7 N4 C16 119.49(15) . . ? C7 N4 S1 120.37(12) . . ? C16 N4 S1 118.46(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.242 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.047 #===END _database_code_depnum_ccdc_archive 'CCDC 929373'