# Electronic Supplementary Material (ESI) for CrystEngComm # 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_KP31 _database_code_depnum_ccdc_archive 'CCDC 906513' #TrackingRef 'KP31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 N10 O4 S2 Zn' _chemical_formula_weight 641.99 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.950(3) _cell_length_b 13.320(3) _cell_length_c 13.850(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3127.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 128(2) _cell_measurement_reflns_used 9239 _cell_measurement_theta_min 1.4704 _cell_measurement_theta_max 31.3816 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7228 _exptl_absorpt_correction_T_max 0.7808 _exptl_absorpt_process_details Crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 128(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11283 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2587 _reflns_number_gt 2493 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1473P)^2^+6.4576P] 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 2587 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.2162 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _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 Zn1 Zn 0.2500 0.5000 -0.07632(4) 0.0193(3) Uani 1 2 d S . . S1 S 0.28078(6) 0.35262(8) -0.15431(7) 0.0205(4) Uani 1 1 d . . . O1 O 0.0437(2) -0.2252(2) -0.0172(3) 0.0380(9) Uani 1 1 d . . . O2 O 0.0376(3) -0.1547(3) 0.1234(3) 0.0463(10) Uani 1 1 d . . . N1 N 0.0508(2) 0.3971(3) 0.0803(3) 0.0267(9) Uani 1 1 d . . . H1X H 0.0488 0.3350 0.0587 0.032 Uiso 1 1 calc R . . N2 N 0.1682(2) 0.4219(2) -0.0052(2) 0.0200(7) Uani 1 1 d . . . N3 N 0.1581(2) 0.3204(3) -0.0285(2) 0.0212(8) Uani 1 1 d . . . N4 N 0.1998(2) 0.1861(3) -0.1229(2) 0.0216(8) Uani 1 1 d . . . H4X H 0.2308 0.1687 -0.1796 0.026 Uiso 1 1 d . . . N5 N 0.0560(2) -0.1544(3) 0.0373(3) 0.0315(9) Uani 1 1 d . . . C1 C -0.0073(3) 0.4294(4) 0.1409(3) 0.0327(11) Uani 1 1 d . . . H1 H -0.0483 0.3845 0.1585 0.039 Uiso 1 1 calc R . . C2 C -0.0078(3) 0.5226(4) 0.1761(3) 0.0328(11) Uani 1 1 d . . . H2 H -0.0478 0.5440 0.2196 0.039 Uiso 1 1 calc R . . C3 C 0.0531(3) 0.5887(4) 0.1464(3) 0.0342(11) Uani 1 1 d . . . H3 H 0.0534 0.6560 0.1689 0.041 Uiso 1 1 calc R . . C4 C 0.1108(3) 0.5567(4) 0.0863(3) 0.0319(11) Uani 1 1 d . . . H4 H 0.1512 0.6018 0.0670 0.038 Uiso 1 1 calc R . . C5 C 0.1113(2) 0.4561(3) 0.0520(3) 0.0207(9) Uani 1 1 d . . . C6 C 0.2053(2) 0.2853(3) -0.0936(3) 0.0187(8) Uani 1 1 d . . . C7 C 0.1625(2) 0.1065(3) -0.0795(3) 0.0190(9) Uani 1 1 d . . . C8 C 0.1326(3) 0.1067(3) 0.0155(3) 0.0277(10) Uani 1 1 d . . . H8 H 0.1356 0.1661 0.0533 0.033 Uiso 1 1 calc R . . C9 C 0.0988(3) 0.0208(4) 0.0541(3) 0.0276(10) Uani 1 1 d . . . H9 H 0.0791 0.0210 0.1183 0.033 Uiso 1 1 calc R . . C10 C 0.0941(2) -0.0651(3) -0.0016(3) 0.0242(9) Uani 1 1 d . . . C11 C 0.1218(2) -0.0672(3) -0.0966(3) 0.0227(9) Uani 1 1 d . . . H11 H 0.1168 -0.1262 -0.1346 0.027 Uiso 1 1 calc R . . C12 C 0.1564(3) 0.0171(3) -0.1341(3) 0.0228(9) Uani 1 1 d . . . H12 H 0.1767 0.0155 -0.1980 0.027 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 Zn1 0.0243(5) 0.0164(5) 0.0172(5) 0.000 0.000 -0.0065(2) S1 0.0224(6) 0.0202(7) 0.0188(5) -0.0016(4) 0.0023(4) -0.0052(4) O1 0.0418(19) 0.0227(19) 0.050(2) -0.0073(15) 0.0112(16) -0.0135(14) O2 0.071(3) 0.032(2) 0.0361(19) 0.0011(15) 0.0191(19) -0.0179(18) N1 0.0270(19) 0.024(2) 0.0292(19) -0.0052(14) 0.0057(14) -0.0042(16) N2 0.0278(17) 0.0117(18) 0.0206(16) -0.0003(13) 0.0046(14) -0.0033(13) N3 0.0276(18) 0.0120(18) 0.0241(17) -0.0020(13) 0.0053(14) -0.0071(13) N4 0.0265(17) 0.0156(19) 0.0227(17) -0.0016(13) 0.0057(14) -0.0064(14) N5 0.034(2) 0.020(2) 0.040(2) -0.0013(16) 0.0086(18) -0.0033(15) C1 0.028(2) 0.036(3) 0.034(2) -0.005(2) 0.0138(19) -0.0088(19) C2 0.035(3) 0.034(3) 0.029(2) -0.007(2) 0.009(2) 0.004(2) C3 0.055(3) 0.019(2) 0.028(2) -0.0014(18) 0.009(2) 0.001(2) C4 0.050(3) 0.018(3) 0.027(2) -0.0036(17) 0.013(2) -0.005(2) C5 0.025(2) 0.018(2) 0.0189(18) 0.0015(16) 0.0037(16) -0.0074(16) C6 0.0229(19) 0.015(2) 0.0183(17) 0.0009(15) -0.0010(15) -0.0019(15) C7 0.021(2) 0.012(2) 0.024(2) 0.0009(14) 0.0019(15) 0.0014(16) C8 0.039(2) 0.022(2) 0.022(2) -0.0035(17) 0.0032(18) -0.0043(19) C9 0.038(3) 0.021(2) 0.024(2) 0.0013(18) 0.0026(19) -0.0055(19) C10 0.025(2) 0.018(2) 0.030(2) 0.0011(17) 0.0012(17) -0.0015(16) C11 0.0201(19) 0.020(2) 0.028(2) -0.0041(17) 0.0033(17) 0.0015(16) C12 0.025(2) 0.021(2) 0.022(2) -0.0035(16) -0.0002(16) 0.0069(17) _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 Zn1 N2 1.994(3) 2_565 y Zn1 N2 1.994(3) . y Zn1 S1 2.3005(11) . y Zn1 S1 2.3005(11) 2_565 y S1 C6 1.774(4) . y O1 N5 1.225(5) . ? O2 N5 1.233(5) . ? N1 C5 1.350(6) . ? N1 C1 1.364(6) . ? N1 H1X 0.8800 . ? N2 C5 1.329(6) . ? N2 N3 1.401(5) . ? N3 C6 1.293(6) . ? N4 C7 1.373(5) . ? N4 C6 1.385(6) . ? N4 H4X 0.9733 . ? N5 C10 1.458(6) . ? C1 C2 1.333(7) . ? C1 H1 0.9500 . ? C2 C3 1.418(7) . ? C2 H2 0.9500 . ? C3 C4 1.353(7) . ? C3 H3 0.9500 . ? C4 C5 1.422(7) . ? C4 H4 0.9500 . ? C7 C8 1.410(6) . ? C7 C12 1.414(6) . ? C8 C9 1.387(7) . ? C8 H8 0.9500 . ? C9 C10 1.383(6) . ? C9 H9 0.9500 . ? C10 C11 1.397(6) . ? C11 C12 1.368(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 N2 Zn1 N2 120.77(19) 2_565 . y N2 Zn1 S1 121.31(10) 2_565 . y N2 Zn1 S1 86.81(10) . . y N2 Zn1 S1 86.81(10) 2_565 2_565 y N2 Zn1 S1 121.31(10) . 2_565 y S1 Zn1 S1 124.00(6) . 2_565 y C6 S1 Zn1 92.59(14) . . ? C5 N1 C1 122.9(4) . . ? C5 N1 H1X 118.6 . . ? C1 N1 H1X 118.6 . . ? C5 N2 N3 112.3(3) . . ? C5 N2 Zn1 128.3(3) . . ? N3 N2 Zn1 118.4(2) . . ? C6 N3 N2 115.7(3) . . ? C7 N4 C6 129.8(3) . . ? C7 N4 H4X 114.7 . . ? C6 N4 H4X 115.3 . . ? O1 N5 O2 123.4(4) . . ? O1 N5 C10 118.4(4) . . ? O2 N5 C10 118.2(4) . . ? C2 C1 N1 121.6(4) . . ? C2 C1 H1 119.2 . . ? N1 C1 H1 119.2 . . ? C1 C2 C3 117.9(4) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N2 C5 N1 121.6(4) . . ? N2 C5 C4 121.8(4) . . ? N1 C5 C4 116.6(4) . . ? N3 C6 N4 120.4(4) . . ? N3 C6 S1 126.5(3) . . ? N4 C6 S1 113.1(3) . . ? N4 C7 C8 124.9(4) . . ? N4 C7 C12 116.8(4) . . ? C8 C7 C12 118.3(4) . . ? C9 C8 C7 120.4(4) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 119.4(4) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.5(4) . . ? C9 C10 N5 119.6(4) . . ? C11 C10 N5 118.8(4) . . ? C12 C11 C10 119.0(4) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C7 121.3(4) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? 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 N2 Zn1 S1 C6 126.47(18) 2_565 . . . ? N2 Zn1 S1 C6 2.01(17) . . . . ? S1 Zn1 S1 C6 -124.16(14) 2_565 . . . ? N2 Zn1 N2 C5 64.9(3) 2_565 . . . ? S1 Zn1 N2 C5 -170.2(4) . . . . ? S1 Zn1 N2 C5 -41.7(4) 2_565 . . . ? N2 Zn1 N2 N3 -127.5(3) 2_565 . . . ? S1 Zn1 N2 N3 -2.5(3) . . . . ? S1 Zn1 N2 N3 125.9(3) 2_565 . . . ? C5 N2 N3 C6 171.4(4) . . . . ? Zn1 N2 N3 C6 1.9(5) . . . . ? C5 N1 C1 C2 0.2(8) . . . . ? N1 C1 C2 C3 1.6(8) . . . . ? C1 C2 C3 C4 -1.7(8) . . . . ? C2 C3 C4 C5 -0.1(8) . . . . ? N3 N2 C5 N1 -1.5(6) . . . . ? Zn1 N2 C5 N1 166.7(3) . . . . ? N3 N2 C5 C4 178.6(4) . . . . ? Zn1 N2 C5 C4 -13.1(6) . . . . ? C1 N1 C5 N2 178.2(4) . . . . ? C1 N1 C5 C4 -1.9(7) . . . . ? C3 C4 C5 N2 -178.3(4) . . . . ? C3 C4 C5 N1 1.8(7) . . . . ? N2 N3 C6 N4 -179.3(4) . . . . ? N2 N3 C6 S1 0.4(5) . . . . ? C7 N4 C6 N3 -16.5(7) . . . . ? C7 N4 C6 S1 163.8(3) . . . . ? Zn1 S1 C6 N3 -2.0(4) . . . . ? Zn1 S1 C6 N4 177.7(3) . . . . ? C6 N4 C7 C8 -11.9(7) . . . . ? C6 N4 C7 C12 170.3(4) . . . . ? N4 C7 C8 C9 -177.2(4) . . . . ? C12 C7 C8 C9 0.5(7) . . . . ? C7 C8 C9 C10 -0.5(7) . . . . ? C8 C9 C10 C11 -0.7(7) . . . . ? C8 C9 C10 N5 -177.7(4) . . . . ? O1 N5 C10 C9 171.1(4) . . . . ? O2 N5 C10 C9 -8.7(6) . . . . ? O1 N5 C10 C11 -6.0(6) . . . . ? O2 N5 C10 C11 174.2(4) . . . . ? C9 C10 C11 C12 1.8(7) . . . . ? N5 C10 C11 C12 178.9(4) . . . . ? C10 C11 C12 C7 -1.8(6) . . . . ? N4 C7 C12 C11 178.6(4) . . . . ? C8 C7 C12 C11 0.6(6) . . . . ? 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 N1 H1X O1 0.88 2.22 2.928(5) 137.2 5 N4 H4X S1 0.97 2.47 3.417(4) 164.9 3_554 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.784 _refine_diff_density_min -0.855 _refine_diff_density_rms 0.199 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 -0.006 0.250 308 64 ' ' 2 0.750 -0.004 0.750 308 64 ' ' 3 0.571 0.250 0.250 12 2 ' ' 4 0.071 0.250 0.750 12 2 ' ' 5 0.929 0.750 0.250 12 2 ' ' 6 0.429 0.750 0.750 12 2 ' ' _platon_squeeze_details ; ; data_KP34 _database_code_depnum_ccdc_archive 'CCDC 906514' #TrackingRef 'KP34.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 F6 N8 S2 Zn' _chemical_formula_weight 687.99 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.125(3) _cell_length_b 13.543(3) _cell_length_c 13.762(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3191.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 128(2) _cell_measurement_reflns_used 14955 _cell_measurement_theta_min 1.7317 _cell_measurement_theta_max 32.0330 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6706 _exptl_absorpt_correction_T_max 0.7875 _exptl_absorpt_process_details Crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 128(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13352 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2795 _reflns_number_gt 2673 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1418P)^2^+9.6045P] 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 2795 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.2734 _refine_ls_wR_factor_gt 0.2327 _refine_ls_goodness_of_fit_ref 1.339 _refine_ls_restrained_S_all 1.339 _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 Zn1 Zn 0.2500 0.0000 -0.07434(7) 0.0193(4) Uani 1 2 d S . . S1 S 0.21753(9) 0.14454(11) -0.15275(11) 0.0211(5) Uani 1 1 d . . . N1 N 0.4475(3) 0.1048(4) 0.0801(4) 0.0262(12) Uani 1 1 d . . . H1X H 0.4489 0.1655 0.0572 0.031 Uiso 1 1 calc R . . N2 N 0.3294(3) 0.0805(4) -0.0011(4) 0.0230(12) Uani 1 1 d . . . N3 N 0.3392(3) 0.1785(3) -0.0270(4) 0.0193(11) Uani 1 1 d . . . N4 N 0.2963(3) 0.3096(4) -0.1213(4) 0.0232(12) Uani 1 1 d . . . H4A H 0.2728 0.3229 -0.1767 0.028 Uiso 1 1 calc R . . C1 C 0.5077(5) 0.0739(6) 0.1378(6) 0.0413(19) Uani 1 1 d . . . H1 H 0.5489 0.1185 0.1526 0.050 Uiso 1 1 calc R . . C2 C 0.5098(5) -0.0172(5) 0.1737(6) 0.0369(17) Uani 1 1 d . . . H2 H 0.5526 -0.0390 0.2120 0.044 Uiso 1 1 calc R . . C3 C 0.4457(5) -0.0814(5) 0.1529(5) 0.0370(18) Uani 1 1 d . . . H3 H 0.4446 -0.1456 0.1806 0.044 Uiso 1 1 calc R . . C4 C 0.3869(5) -0.0522(5) 0.0947(5) 0.0312(16) Uani 1 1 d . . . H4 H 0.3461 -0.0971 0.0791 0.037 Uiso 1 1 calc R . . C5 C 0.3853(4) 0.0466(4) 0.0559(4) 0.0211(13) Uani 1 1 d . . . C6 C 0.2917(4) 0.2108(5) -0.0915(4) 0.0221(13) Uani 1 1 d . . . C7 C 0.3330(4) 0.3911(5) -0.0758(4) 0.0217(13) Uani 1 1 d . . . C8 C 0.3572(4) 0.3926(5) 0.0212(5) 0.0332(16) Uani 1 1 d . . . H8 H 0.3520 0.3352 0.0603 0.040 Uiso 1 1 calc R . . C9 C 0.3884(5) 0.4769(5) 0.0600(5) 0.0306(16) Uani 1 1 d . . . H9 H 0.4057 0.4769 0.1256 0.037 Uiso 1 1 calc R . . C10 C 0.3952(4) 0.5628(5) 0.0049(5) 0.0265(14) Uani 1 1 d . . . C11 C 0.3723(4) 0.5625(5) -0.0932(5) 0.0228(13) Uani 1 1 d . . . H11 H 0.3772 0.6200 -0.1322 0.027 Uiso 1 1 calc R . . C12 C 0.3419(4) 0.4746(4) -0.1318(5) 0.0209(13) Uani 1 1 d . . . H12 H 0.3272 0.4726 -0.1983 0.025 Uiso 1 1 calc R . . C13 C 0.4227(4) 0.6561(5) 0.0485(6) 0.0328(16) Uani 1 1 d . . . F1 F 0.4753(3) 0.6438(3) 0.1200(3) 0.0454(12) Uani 1 1 d . . . F2 F 0.4565(3) 0.7175(3) -0.0156(3) 0.0447(12) Uani 1 1 d . . . F3 F 0.3638(3) 0.7080(3) 0.0895(4) 0.0577(15) 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 Zn1 0.0207(7) 0.0152(6) 0.0221(6) 0.000 0.000 -0.0042(4) S1 0.0215(9) 0.0173(8) 0.0245(8) 0.0011(6) -0.0027(6) -0.0038(6) N1 0.030(3) 0.021(3) 0.027(3) 0.001(2) -0.004(2) -0.001(2) N2 0.026(3) 0.020(2) 0.023(3) 0.006(2) -0.005(2) -0.009(2) N3 0.022(3) 0.008(2) 0.028(3) -0.0015(19) -0.002(2) -0.0021(19) N4 0.028(3) 0.013(2) 0.029(3) -0.003(2) -0.008(2) -0.002(2) C1 0.028(4) 0.053(5) 0.043(4) 0.008(4) -0.012(3) -0.005(3) C2 0.042(5) 0.029(4) 0.040(4) 0.000(3) -0.017(4) 0.004(3) C3 0.049(5) 0.029(4) 0.033(4) 0.004(3) -0.015(3) -0.003(3) C4 0.045(4) 0.021(3) 0.028(3) 0.005(3) -0.014(3) -0.013(3) C5 0.023(3) 0.017(3) 0.024(3) -0.002(2) 0.001(3) -0.008(2) C6 0.022(3) 0.022(3) 0.023(3) -0.003(2) 0.004(2) -0.006(2) C7 0.017(3) 0.021(3) 0.027(3) -0.006(2) -0.001(2) -0.002(3) C8 0.043(4) 0.036(4) 0.021(3) 0.009(3) -0.001(3) -0.007(3) C9 0.038(4) 0.027(3) 0.027(3) 0.001(3) -0.004(3) -0.001(3) C10 0.021(3) 0.026(3) 0.032(3) 0.001(3) 0.003(3) -0.001(3) C11 0.019(3) 0.021(3) 0.029(3) 0.007(2) 0.001(3) -0.004(2) C12 0.021(3) 0.017(3) 0.024(3) -0.002(2) -0.001(3) 0.000(2) C13 0.031(4) 0.020(3) 0.048(4) -0.002(3) -0.002(3) -0.002(3) F1 0.059(3) 0.036(2) 0.042(2) 0.0015(18) -0.020(2) -0.017(2) F2 0.055(3) 0.026(2) 0.054(3) 0.0045(19) -0.010(2) -0.020(2) F3 0.047(3) 0.033(3) 0.093(4) -0.025(3) 0.005(3) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.013(5) 2 y Zn1 N2 2.013(5) . y Zn1 S1 2.3034(16) 2 y Zn1 S1 2.3034(16) . y S1 C6 1.768(6) . y N1 C1 1.367(9) . ? N1 C5 1.367(8) . ? N1 H1X 0.8800 . ? N2 C5 1.320(8) . ? N2 N3 1.384(7) . ? N3 C6 1.282(8) . ? N4 C6 1.401(8) . ? N4 C7 1.417(8) . ? N4 H4A 0.8800 . ? C1 C2 1.330(11) . ? C1 H1 0.9500 . ? C2 C3 1.429(11) . ? C2 H2 0.9500 . ? C3 C4 1.346(10) . ? C3 H3 0.9500 . ? C4 C5 1.441(9) . ? C4 H4 0.9500 . ? C7 C12 1.377(9) . ? C7 C8 1.399(9) . ? C8 C9 1.368(10) . ? C8 H8 0.9500 . ? C9 C10 1.394(9) . ? C9 H9 0.9500 . ? C10 C11 1.405(9) . ? C10 C13 1.476(9) . ? C11 C12 1.403(9) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 F1 1.344(9) . ? C13 F2 1.344(8) . ? C13 F3 1.353(9) . ? 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 N2 Zn1 N2 119.9(3) 2 . y N2 Zn1 S1 86.41(15) 2 2 y N2 Zn1 S1 122.11(16) . 2 y N2 Zn1 S1 122.11(16) 2 . y N2 Zn1 S1 86.41(15) . . y S1 Zn1 S1 124.13(9) 2 . y C6 S1 Zn1 92.0(2) . . ? C1 N1 C5 123.6(6) . . ? C1 N1 H1X 118.2 . . ? C5 N1 H1X 118.2 . . ? C5 N2 N3 113.5(5) . . ? C5 N2 Zn1 126.8(4) . . ? N3 N2 Zn1 118.2(4) . . ? C6 N3 N2 115.4(5) . . ? C6 N4 C7 129.8(5) . . ? C6 N4 H4A 115.1 . . ? C7 N4 H4A 115.1 . . ? C2 C1 N1 121.3(7) . . ? C2 C1 H1 119.3 . . ? N1 C1 H1 119.3 . . ? C1 C2 C3 118.0(7) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 121.0(7) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.5(6) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N2 C5 N1 120.6(5) . . ? N2 C5 C4 123.9(6) . . ? N1 C5 C4 115.5(6) . . ? N3 C6 N4 119.5(5) . . ? N3 C6 S1 127.8(5) . . ? N4 C6 S1 112.6(5) . . ? C12 C7 C8 119.3(6) . . ? C12 C7 N4 116.2(5) . . ? C8 C7 N4 124.4(6) . . ? C9 C8 C7 120.0(6) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.1(6) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 119.8(6) . . ? C9 C10 C13 121.3(6) . . ? C11 C10 C13 118.9(6) . . ? C12 C11 C10 118.0(6) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C7 C12 C11 121.7(6) . . ? C7 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? F1 C13 F2 105.6(6) . . ? F1 C13 F3 105.0(6) . . ? F2 C13 F3 105.8(6) . . ? F1 C13 C10 113.9(6) . . ? F2 C13 C10 113.6(6) . . ? F3 C13 C10 112.1(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Zn1 S1 C6 126.4(3) 2 . . . ? N2 Zn1 S1 C6 3.0(3) . . . . ? S1 Zn1 S1 C6 -123.9(2) 2 . . . ? N2 Zn1 N2 C5 64.8(5) 2 . . . ? S1 Zn1 N2 C5 -41.2(6) 2 . . . ? S1 Zn1 N2 C5 -169.8(5) . . . . ? N2 Zn1 N2 N3 -130.3(5) 2 . . . ? S1 Zn1 N2 N3 123.7(4) 2 . . . ? S1 Zn1 N2 N3 -5.0(4) . . . . ? C5 N2 N3 C6 171.9(6) . . . . ? Zn1 N2 N3 C6 5.1(7) . . . . ? C5 N1 C1 C2 0.9(12) . . . . ? N1 C1 C2 C3 -2.1(12) . . . . ? C1 C2 C3 C4 3.3(12) . . . . ? C2 C3 C4 C5 -3.2(12) . . . . ? N3 N2 C5 N1 -3.4(9) . . . . ? Zn1 N2 C5 N1 162.1(5) . . . . ? N3 N2 C5 C4 178.2(6) . . . . ? Zn1 N2 C5 C4 -16.4(10) . . . . ? C1 N1 C5 N2 -179.2(7) . . . . ? C1 N1 C5 C4 -0.6(10) . . . . ? C3 C4 C5 N2 -179.6(7) . . . . ? C3 C4 C5 N1 1.8(11) . . . . ? N2 N3 C6 N4 179.0(5) . . . . ? N2 N3 C6 S1 -1.8(8) . . . . ? C7 N4 C6 N3 -17.7(10) . . . . ? C7 N4 C6 S1 163.0(5) . . . . ? Zn1 S1 C6 N3 -1.7(6) . . . . ? Zn1 S1 C6 N4 177.5(4) . . . . ? C6 N4 C7 C12 166.8(6) . . . . ? C6 N4 C7 C8 -15.8(11) . . . . ? C12 C7 C8 C9 0.9(11) . . . . ? N4 C7 C8 C9 -176.5(7) . . . . ? C7 C8 C9 C10 1.3(12) . . . . ? C8 C9 C10 C11 -2.2(11) . . . . ? C8 C9 C10 C13 174.9(7) . . . . ? C9 C10 C11 C12 0.9(9) . . . . ? C13 C10 C11 C12 -176.2(6) . . . . ? C8 C7 C12 C11 -2.2(10) . . . . ? N4 C7 C12 C11 175.4(6) . . . . ? C10 C11 C12 C7 1.3(10) . . . . ? C9 C10 C13 F1 32.8(10) . . . . ? C11 C10 C13 F1 -150.1(6) . . . . ? C9 C10 C13 F2 153.8(7) . . . . ? C11 C10 C13 F2 -29.1(9) . . . . ? C9 C10 C13 F3 -86.3(8) . . . . ? C11 C10 C13 F3 90.8(8) . . . . ? 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 N1 H1X F2 0.88 2.34 3.046(7) 137.7 5_665 N4 H4A S1 0.88 2.57 3.445(6) 173.9 3_554 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.814 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.231 data_kp4t _database_code_depnum_ccdc_archive 'CCDC 906515' #TrackingRef 'KP4T.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 F N4 S' _chemical_formula_weight 262.31 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.928(2) _cell_length_b 11.123(2) _cell_length_c 12.860(3) _cell_angle_alpha 74.09(3) _cell_angle_beta 89.89(3) _cell_angle_gamma 65.90(3) _cell_volume 1236.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 2856 _cell_measurement_theta_min 1.6655 _cell_measurement_theta_max 31.1782 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8719 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8664 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4139 _reflns_number_gt 3931 _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. All non H ANIS. No solvent No Disorder. All H calc and ride except NH protons which were found and freely refined. ; _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^)+(0.0271P)^2^+0.9301P] 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 4139 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 0.36330(6) 0.35010(6) 0.04171(5) 0.02123(15) Uani 1 1 d . . . N1 N -0.1159(2) 0.47698(19) 0.33938(15) 0.0208(4) Uani 1 1 d . . . N2 N 0.0096(2) 0.48115(19) 0.19017(15) 0.0193(4) Uani 1 1 d . . . N2X H -0.071(3) 0.558(3) 0.157(2) 0.030(7) Uiso 1 1 d . . . N3 N 0.1419(2) 0.46310(19) 0.14607(16) 0.0216(4) Uani 1 1 d . . . H3X H 0.192(3) 0.508(3) 0.159(2) 0.037(8) Uiso 1 1 d . . . N4 N 0.1218(2) 0.29865(18) 0.08123(15) 0.0181(4) Uani 1 1 d . . . H4X H 0.043(3) 0.315(3) 0.112(2) 0.043(9) Uiso 1 1 d . . . F1 F 0.25555(15) -0.13351(14) -0.09183(12) 0.0323(3) Uani 1 1 d . . . C1 C -0.1197(3) 0.4273(2) 0.44666(19) 0.0269(5) Uani 1 1 d . . . H1 H -0.2131 0.4577 0.4737 0.032 Uiso 1 1 calc R . . C2 C 0.0047(3) 0.3349(3) 0.5193(2) 0.0324(6) Uani 1 1 d . . . H2 H -0.0023 0.3018 0.5946 0.039 Uiso 1 1 calc R . . C3 C 0.1402(3) 0.2917(2) 0.4790(2) 0.0335(6) Uani 1 1 d . . . H3 H 0.2283 0.2288 0.5272 0.040 Uiso 1 1 calc R . . C4 C 0.1479(3) 0.3392(2) 0.3696(2) 0.0261(5) Uani 1 1 d . . . H4 H 0.2400 0.3100 0.3406 0.031 Uiso 1 1 calc R . . C5 C 0.0154(2) 0.4319(2) 0.30294(17) 0.0176(5) Uani 1 1 d . . . C6 C 0.2004(2) 0.3686(2) 0.09196(17) 0.0179(5) Uani 1 1 d . . . C7 C 0.1628(2) 0.1894(2) 0.03244(16) 0.0166(4) Uani 1 1 d . . . C8 C 0.0532(2) 0.1898(2) -0.03487(18) 0.0213(5) Uani 1 1 d . . . H8 H -0.0432 0.2642 -0.0511 0.026 Uiso 1 1 calc R . . C9 C 0.0848(3) 0.0814(2) -0.07829(18) 0.0239(5) Uani 1 1 d . . . H9 H 0.0117 0.0815 -0.1260 0.029 Uiso 1 1 calc R . . C10 C 0.2238(3) -0.0260(2) -0.05082(18) 0.0215(5) Uani 1 1 d . . . C11 C 0.3335(3) -0.0299(2) 0.01697(18) 0.0219(5) Uani 1 1 d . . . H11 H 0.4287 -0.1058 0.0343 0.026 Uiso 1 1 calc R . . C12 C 0.3024(2) 0.0791(2) 0.05954(17) 0.0192(5) Uani 1 1 d . . . H12 H 0.3762 0.0783 0.1070 0.023 Uiso 1 1 calc R . . S21 S 0.28723(6) 0.64777(6) 0.22942(5) 0.02637(16) Uani 1 1 d . . . N21 N 0.91829(19) 0.22638(18) 0.21362(14) 0.0182(4) Uani 1 1 d . . . N22 N 0.6879(2) 0.40463(19) 0.18848(16) 0.0192(4) Uani 1 1 d . . . H22X H 0.709(3) 0.441(3) 0.122(2) 0.031(7) Uiso 1 1 d . . . N23 N 0.5379(2) 0.45523(19) 0.20278(16) 0.0213(4) Uani 1 1 d . . . H23X H 0.483(3) 0.434(3) 0.165(2) 0.029(7) Uiso 1 1 d . . . N24 N 0.5690(2) 0.61744(19) 0.26361(15) 0.0202(4) Uani 1 1 d . . . H24X H 0.661(3) 0.571(3) 0.2622(19) 0.022(7) Uiso 1 1 d . . . F21 F 0.47030(15) 1.08922(14) 0.37595(12) 0.0313(3) Uani 1 1 d . . . C21 C 1.0178(2) 0.0967(2) 0.26635(18) 0.0212(5) Uani 1 1 d . . . H21 H 1.1142 0.0646 0.2440 0.025 Uiso 1 1 calc R . . C22 C 0.9876(3) 0.0085(2) 0.35032(18) 0.0243(5) Uani 1 1 d . . . H22 H 1.0602 -0.0827 0.3846 0.029 Uiso 1 1 calc R . . C23 C 0.8471(3) 0.0572(2) 0.38363(19) 0.0261(5) Uani 1 1 d . . . H23 H 0.8230 -0.0009 0.4423 0.031 Uiso 1 1 calc R . . C24 C 0.7423(2) 0.1895(2) 0.33206(18) 0.0214(5) Uani 1 1 d . . . H24 H 0.6459 0.2243 0.3541 0.026 Uiso 1 1 calc R . . C25 C 0.7837(2) 0.2699(2) 0.24629(17) 0.0173(5) Uani 1 1 d . . . C26 C 0.4742(2) 0.5725(2) 0.23283(17) 0.0194(5) Uani 1 1 d . . . C27 C 0.5363(2) 0.7402(2) 0.29265(17) 0.0182(5) Uani 1 1 d . . . C28 C 0.6157(2) 0.8160(2) 0.24996(17) 0.0196(5) Uani 1 1 d . . . H28 H 0.6852 0.7868 0.2012 0.024 Uiso 1 1 calc R . . C29 C 0.5947(2) 0.9342(2) 0.27763(17) 0.0203(5) Uani 1 1 d . . . H29 H 0.6494 0.9861 0.2490 0.024 Uiso 1 1 calc R . . C30 C 0.4924(2) 0.9736(2) 0.34770(18) 0.0220(5) Uani 1 1 d . . . C31 C 0.4125(3) 0.8999(3) 0.3917(2) 0.0276(5) Uani 1 1 d . . . H31 H 0.3425 0.9300 0.4399 0.033 Uiso 1 1 calc R . . C32 C 0.4355(3) 0.7813(2) 0.36458(19) 0.0252(5) Uani 1 1 d . . . H32 H 0.3826 0.7284 0.3951 0.030 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 0.0192(3) 0.0223(3) 0.0247(3) -0.0089(2) 0.0076(2) -0.0100(2) N1 0.0201(10) 0.0230(10) 0.0227(10) -0.0100(8) 0.0030(8) -0.0105(8) N2 0.0117(10) 0.0207(10) 0.0236(10) -0.0080(8) 0.0033(8) -0.0042(8) N3 0.0171(10) 0.0221(10) 0.0308(11) -0.0131(8) 0.0081(8) -0.0100(8) N4 0.0153(10) 0.0203(10) 0.0199(10) -0.0082(8) 0.0044(8) -0.0073(8) F1 0.0333(8) 0.0338(8) 0.0402(9) -0.0253(7) 0.0068(6) -0.0152(7) C1 0.0335(14) 0.0321(13) 0.0240(12) -0.0122(10) 0.0091(10) -0.0202(11) C2 0.0491(17) 0.0287(13) 0.0213(13) -0.0014(10) -0.0025(11) -0.0223(12) C3 0.0364(15) 0.0232(12) 0.0319(14) 0.0002(10) -0.0123(11) -0.0092(11) C4 0.0209(13) 0.0217(12) 0.0331(14) -0.0090(10) -0.0005(10) -0.0058(10) C5 0.0164(12) 0.0163(10) 0.0214(11) -0.0070(9) 0.0005(9) -0.0072(9) C6 0.0175(12) 0.0153(10) 0.0169(11) -0.0021(8) -0.0007(8) -0.0048(9) C7 0.0186(12) 0.0198(11) 0.0137(10) -0.0054(8) 0.0049(8) -0.0101(9) C8 0.0169(12) 0.0220(11) 0.0232(12) -0.0051(9) 0.0002(9) -0.0077(9) C9 0.0255(13) 0.0298(13) 0.0208(12) -0.0076(10) -0.0009(9) -0.0161(11) C10 0.0268(13) 0.0232(11) 0.0209(11) -0.0121(9) 0.0080(9) -0.0133(10) C11 0.0191(12) 0.0211(11) 0.0234(12) -0.0080(9) 0.0029(9) -0.0057(9) C12 0.0182(12) 0.0224(11) 0.0177(11) -0.0071(9) 0.0006(9) -0.0085(9) S21 0.0144(3) 0.0274(3) 0.0399(4) -0.0172(3) 0.0020(2) -0.0069(2) N21 0.0161(10) 0.0201(9) 0.0202(10) -0.0084(8) 0.0028(7) -0.0078(8) N22 0.0147(10) 0.0204(9) 0.0219(10) -0.0065(8) 0.0054(8) -0.0068(8) N23 0.0136(10) 0.0244(10) 0.0283(11) -0.0112(8) 0.0028(8) -0.0082(8) N24 0.0136(10) 0.0232(10) 0.0253(10) -0.0112(8) 0.0030(8) -0.0067(8) F21 0.0297(8) 0.0279(7) 0.0406(8) -0.0216(6) 0.0045(6) -0.0092(6) C21 0.0172(12) 0.0230(12) 0.0243(12) -0.0097(9) 0.0020(9) -0.0077(9) C22 0.0235(13) 0.0241(12) 0.0227(12) -0.0056(9) 0.0013(10) -0.0084(10) C23 0.0313(14) 0.0269(12) 0.0204(12) -0.0053(10) 0.0078(10) -0.0138(11) C24 0.0195(12) 0.0245(12) 0.0236(12) -0.0104(9) 0.0083(9) -0.0106(10) C25 0.0179(12) 0.0188(11) 0.0194(11) -0.0100(9) 0.0017(9) -0.0091(9) C26 0.0187(12) 0.0223(11) 0.0179(11) -0.0053(9) 0.0030(9) -0.0098(9) C27 0.0143(11) 0.0196(11) 0.0187(11) -0.0070(9) -0.0005(8) -0.0046(9) C28 0.0167(12) 0.0237(11) 0.0161(11) -0.0060(9) 0.0016(8) -0.0061(9) C29 0.0180(12) 0.0216(11) 0.0184(11) -0.0029(9) -0.0020(9) -0.0075(9) C30 0.0197(12) 0.0194(11) 0.0237(12) -0.0111(9) -0.0027(9) -0.0022(9) C31 0.0189(13) 0.0406(14) 0.0296(13) -0.0208(11) 0.0088(10) -0.0121(11) C32 0.0214(13) 0.0356(13) 0.0267(12) -0.0148(10) 0.0087(10) -0.0166(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 C6 1.695(2) . ? N1 C5 1.328(3) . ? N1 C1 1.345(3) . ? N2 N3 1.389(3) . ? N2 C5 1.395(3) . ? N2 N2X 0.89(3) . ? N3 C6 1.351(3) . ? N3 H3X 0.88(3) . ? N4 C6 1.338(3) . ? N4 C7 1.432(3) . ? N4 H4X 0.85(3) . ? F1 C10 1.358(2) . ? C1 C2 1.377(4) . ? C1 H1 0.9500 . ? C2 C3 1.384(4) . ? C2 H2 0.9500 . ? C3 C4 1.375(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(3) . ? C4 H4 0.9500 . ? C7 C12 1.388(3) . ? C7 C8 1.390(3) . ? C8 C9 1.387(3) . ? C8 H8 0.9500 . ? C9 C10 1.372(3) . ? C9 H9 0.9500 . ? C10 C11 1.375(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? S21 C26 1.691(2) . ? N21 C25 1.334(3) . ? N21 C21 1.349(3) . ? N22 C25 1.389(3) . ? N22 N23 1.393(3) . ? N22 H22X 0.90(3) . ? N23 C26 1.361(3) . ? N23 H23X 0.87(3) . ? N24 C26 1.337(3) . ? N24 C27 1.424(3) . ? N24 H24X 0.85(2) . ? F21 C30 1.363(2) . ? C21 C22 1.369(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C23 C24 1.380(3) . ? C23 H23 0.9500 . ? C24 C25 1.394(3) . ? C24 H24 0.9500 . ? C27 C32 1.386(3) . ? C27 C28 1.386(3) . ? C28 C29 1.389(3) . ? C28 H28 0.9500 . ? C29 C30 1.373(3) . ? C29 H29 0.9500 . ? C30 C31 1.377(3) . ? C31 C32 1.386(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 C5 N1 C1 117.3(2) . . ? N3 N2 C5 118.56(18) . . ? N3 N2 N2X 117.2(17) . . ? C5 N2 N2X 115.4(17) . . ? C6 N3 N2 120.61(19) . . ? C6 N3 H3X 119.8(18) . . ? N2 N3 H3X 119.3(18) . . ? C6 N4 C7 127.03(19) . . ? C6 N4 H4X 116(2) . . ? C7 N4 H4X 116(2) . . ? N1 C1 C2 123.4(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 117.8(2) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 117.3(2) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? N1 C5 C4 123.7(2) . . ? N1 C5 N2 114.19(19) . . ? C4 C5 N2 122.0(2) . . ? N4 C6 N3 116.28(19) . . ? N4 C6 S1 125.44(17) . . ? N3 C6 S1 118.27(17) . . ? C12 C7 C8 120.5(2) . . ? C12 C7 N4 121.50(19) . . ? C8 C7 N4 117.65(19) . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 118.5(2) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? F1 C10 C9 119.1(2) . . ? F1 C10 C11 118.2(2) . . ? C9 C10 C11 122.7(2) . . ? C10 C11 C12 118.8(2) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C11 C12 C7 119.6(2) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C25 N21 C21 117.42(19) . . ? C25 N22 N23 119.57(18) . . ? C25 N22 H22X 117.5(16) . . ? N23 N22 H22X 115.7(16) . . ? C26 N23 N22 119.45(19) . . ? C26 N23 H23X 119.0(17) . . ? N22 N23 H23X 115.9(17) . . ? C26 N24 C27 128.49(19) . . ? C26 N24 H24X 117.6(17) . . ? C27 N24 H24X 113.7(17) . . ? N21 C21 C22 123.7(2) . . ? N21 C21 H21 118.2 . . ? C22 C21 H21 118.2 . . ? C21 C22 C23 117.7(2) . . ? C21 C22 H22 121.2 . . ? C23 C22 H22 121.2 . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 117.3(2) . . ? C23 C24 H24 121.4 . . ? C25 C24 H24 121.4 . . ? N21 C25 N22 113.98(19) . . ? N21 C25 C24 123.5(2) . . ? N22 C25 C24 122.5(2) . . ? N24 C26 N23 115.30(19) . . ? N24 C26 S21 125.69(17) . . ? N23 C26 S21 119.01(17) . . ? C32 C27 C28 120.0(2) . . ? C32 C27 N24 122.7(2) . . ? C28 C27 N24 117.15(19) . . ? C27 C28 C29 120.8(2) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 117.9(2) . . ? C30 C29 H29 121.0 . . ? C28 C29 H29 121.0 . . ? F21 C30 C29 118.8(2) . . ? F21 C30 C31 118.7(2) . . ? C29 C30 C31 122.5(2) . . ? C30 C31 C32 119.1(2) . . ? C30 C31 H31 120.4 . . ? C32 C31 H31 120.4 . . ? C31 C32 C27 119.6(2) . . ? C31 C32 H32 120.2 . . ? C27 C32 H32 120.2 . . ? 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 C5 N2 N3 C6 106.6(2) . . . . ? C5 N1 C1 C2 0.8(3) . . . . ? N1 C1 C2 C3 0.2(4) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C1 N1 C5 C4 -1.2(3) . . . . ? C1 N1 C5 N2 176.27(19) . . . . ? C3 C4 C5 N1 0.6(3) . . . . ? C3 C4 C5 N2 -176.7(2) . . . . ? N3 N2 C5 N1 167.37(18) . . . . ? N3 N2 C5 C4 -15.1(3) . . . . ? C7 N4 C6 N3 -176.74(19) . . . . ? C7 N4 C6 S1 4.4(3) . . . . ? N2 N3 C6 N4 1.9(3) . . . . ? N2 N3 C6 S1 -179.13(15) . . . . ? C6 N4 C7 C12 48.5(3) . . . . ? C6 N4 C7 C8 -137.9(2) . . . . ? C12 C7 C8 C9 -2.1(3) . . . . ? N4 C7 C8 C9 -175.75(19) . . . . ? C7 C8 C9 C10 1.7(3) . . . . ? C8 C9 C10 F1 179.25(19) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? F1 C10 C11 C12 -179.87(19) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C7 -0.5(3) . . . . ? C8 C7 C12 C11 1.5(3) . . . . ? N4 C7 C12 C11 174.87(19) . . . . ? C25 N22 N23 C26 124.4(2) . . . . ? C25 N21 C21 C22 0.2(3) . . . . ? N21 C21 C22 C23 -1.1(3) . . . . ? C21 C22 C23 C24 0.8(3) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? C21 N21 C25 N22 179.67(19) . . . . ? C21 N21 C25 C24 0.9(3) . . . . ? N23 N22 C25 N21 170.06(18) . . . . ? N23 N22 C25 C24 -11.2(3) . . . . ? C23 C24 C25 N21 -1.1(3) . . . . ? C23 C24 C25 N22 -179.8(2) . . . . ? C27 N24 C26 N23 175.7(2) . . . . ? C27 N24 C26 S21 -4.7(3) . . . . ? N22 N23 C26 N24 -10.5(3) . . . . ? N22 N23 C26 S21 169.81(16) . . . . ? C26 N24 C27 C32 47.7(3) . . . . ? C26 N24 C27 C28 -135.5(2) . . . . ? C32 C27 C28 C29 -0.6(3) . . . . ? N24 C27 C28 C29 -177.49(19) . . . . ? C27 C28 C29 C30 -0.5(3) . . . . ? C28 C29 C30 F21 179.91(19) . . . . ? C28 C29 C30 C31 0.8(3) . . . . ? F21 C30 C31 C32 -179.2(2) . . . . ? C29 C30 C31 C32 0.0(4) . . . . ? C30 C31 C32 C27 -1.0(4) . . . . ? C28 C27 C32 C31 1.3(3) . . . . ? N24 C27 C32 C31 178.1(2) . . . . ? 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 N3 H3X S21 0.88(3) 2.47(3) 3.329(2) 165(2) . N4 H4X N21 0.85(3) 2.12(3) 2.861(3) 145(3) 1_455 N22 H22X S1 0.90(3) 2.51(3) 3.303(2) 146(2) 2_665 N23 H23X S1 0.87(3) 2.56(3) 3.414(2) 170(2) . N24 H24X N1 0.85(2) 2.13(3) 2.892(3) 149(2) 1_655 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.227 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.046 data_kp6 _database_code_depnum_ccdc_archive 'CCDC 906516' #TrackingRef 'KP6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N4 S' _chemical_formula_weight 272.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.7107(8) _cell_length_b 16.0126(15) _cell_length_c 20.772(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2897.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 2856 _cell_measurement_theta_min 1.6655 _cell_measurement_theta_max 31.1782 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9110 _exptl_absorpt_correction_T_max 0.9480 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15239 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2555 _reflns_number_gt 2212 _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. All non-H ANIS. No solvent. No disorder. H calc and ride except NH protons which were found and AFIX 01'd ; _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^)+(0.0502P)^2^+1.1501P] 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 2555 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0992 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.38155(5) 0.01996(3) 0.33885(2) 0.04537(17) Uani 1 1 d . . . N1 N -0.21526(15) 0.19917(9) 0.28389(6) 0.0355(3) Uani 1 1 d . . . N2 N -0.04132(15) 0.09454(8) 0.30574(6) 0.0342(3) Uani 1 1 d . . . H2X H -0.0848 0.0722 0.2706 0.041 Uiso 1 1 d . . . N3 N 0.11777(15) 0.08184(9) 0.30208(6) 0.0365(3) Uani 1 1 d . . . H3X H 0.1708 0.1131 0.2742 0.044 Uiso 1 1 d . . . N4 N 0.10591(14) 0.00204(9) 0.39304(6) 0.0330(3) Uani 1 1 d . . . H4X H 0.0140 0.0127 0.3925 0.040 Uiso 1 1 d . . . C1 C -0.2601(2) 0.27912(12) 0.28882(8) 0.0455(5) Uani 1 1 d . . . H1 H -0.3527 0.2953 0.2681 0.055 Uiso 1 1 calc R . . C2 C -0.1795(2) 0.33888(12) 0.32211(9) 0.0502(5) Uani 1 1 d . . . H2 H -0.2143 0.3951 0.3234 0.060 Uiso 1 1 calc R . . C3 C -0.0466(2) 0.31546(12) 0.35376(9) 0.0463(5) Uani 1 1 d . . . H3 H 0.0102 0.3551 0.3781 0.056 Uiso 1 1 calc R . . C4 C 0.00201(19) 0.23418(11) 0.34950(8) 0.0389(4) Uani 1 1 d . . . H4 H 0.0926 0.2163 0.3709 0.047 Uiso 1 1 calc R . . C5 C -0.08432(18) 0.17845(10) 0.31308(7) 0.0322(4) Uani 1 1 d . . . C6 C 0.19091(19) 0.03497(10) 0.34585(7) 0.0320(4) Uani 1 1 d . . . C7 C 0.16760(17) -0.04657(10) 0.44464(7) 0.0308(4) Uani 1 1 d . . . C8 C 0.16126(19) -0.13326(11) 0.44089(9) 0.0397(4) Uani 1 1 d . . . C9 C 0.2212(2) -0.17841(13) 0.49280(11) 0.0549(6) Uani 1 1 d . . . H9 H 0.2180 -0.2377 0.4922 0.066 Uiso 1 1 calc R . . C10 C 0.2853(2) -0.13758(16) 0.54505(10) 0.0594(6) Uani 1 1 d . . . H10 H 0.3263 -0.1691 0.5798 0.071 Uiso 1 1 calc R . . C11 C 0.2899(2) -0.05267(15) 0.54711(9) 0.0521(5) Uani 1 1 d . . . H11 H 0.3341 -0.0257 0.5834 0.063 Uiso 1 1 calc R . . C12 C 0.23126(19) -0.00510(12) 0.49730(8) 0.0375(4) Uani 1 1 d . . . C13 C 0.0939(3) -0.17598(13) 0.38355(11) 0.0597(6) Uani 1 1 d . . . H13A H -0.0153 -0.1619 0.3802 0.072 Uiso 1 1 calc R . . H13B H 0.1053 -0.2366 0.3883 0.072 Uiso 1 1 calc R . . H13C H 0.1474 -0.1575 0.3446 0.072 Uiso 1 1 calc R . . C14 C 0.2402(2) 0.08871(12) 0.49872(9) 0.0531(5) Uani 1 1 d . . . H14A H 0.2743 0.1071 0.5414 0.064 Uiso 1 1 calc R . . H14B H 0.1386 0.1122 0.4896 0.064 Uiso 1 1 calc R . . H14C H 0.3134 0.1079 0.4661 0.064 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 0.0303(3) 0.0676(3) 0.0383(3) 0.0181(2) 0.00391(18) 0.0118(2) N1 0.0349(8) 0.0466(8) 0.0251(7) -0.0053(6) -0.0022(5) 0.0089(6) N2 0.0288(7) 0.0452(8) 0.0286(7) 0.0004(6) -0.0058(5) 0.0035(6) N3 0.0289(7) 0.0523(9) 0.0281(7) 0.0087(6) 0.0001(5) 0.0053(6) N4 0.0263(7) 0.0457(8) 0.0270(7) 0.0058(6) -0.0021(5) 0.0031(6) C1 0.0491(10) 0.0563(11) 0.0313(9) -0.0076(8) -0.0026(8) 0.0189(9) C2 0.0642(13) 0.0459(11) 0.0405(10) -0.0092(8) 0.0052(9) 0.0111(10) C3 0.0492(11) 0.0530(11) 0.0367(9) -0.0111(8) 0.0074(8) -0.0093(9) C4 0.0321(8) 0.0536(11) 0.0311(9) -0.0019(7) 0.0007(7) -0.0031(8) C5 0.0309(8) 0.0452(9) 0.0207(7) 0.0021(6) 0.0024(6) 0.0024(7) C6 0.0339(9) 0.0386(9) 0.0237(8) -0.0005(6) -0.0028(6) 0.0030(7) C7 0.0257(7) 0.0385(9) 0.0282(8) 0.0053(6) 0.0008(6) 0.0004(7) C8 0.0338(9) 0.0401(9) 0.0451(10) 0.0020(8) 0.0085(7) -0.0017(7) C9 0.0535(12) 0.0423(10) 0.0690(14) 0.0231(10) 0.0216(10) 0.0108(9) C10 0.0515(12) 0.0867(16) 0.0401(11) 0.0286(11) 0.0053(9) 0.0205(11) C11 0.0443(11) 0.0825(15) 0.0296(9) 0.0074(9) -0.0048(8) 0.0053(10) C12 0.0326(9) 0.0520(10) 0.0279(8) 0.0006(7) 0.0004(7) -0.0013(7) C13 0.0572(13) 0.0499(12) 0.0720(14) -0.0180(10) 0.0036(11) -0.0080(10) C14 0.0584(12) 0.0551(12) 0.0459(11) -0.0138(9) 0.0002(9) -0.0107(9) _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 C6 1.6842(17) . ? N1 C5 1.334(2) . ? N1 C1 1.342(2) . ? N2 N3 1.4027(18) . ? N2 C5 1.403(2) . ? N2 H2X 0.8962 . ? N3 C6 1.340(2) . ? N3 H3X 0.8937 . ? N4 C6 1.337(2) . ? N4 C7 1.4295(19) . ? N4 H4X 0.8188 . ? C1 C2 1.374(3) . ? C1 H1 0.9500 . ? C2 C3 1.384(3) . ? C2 H2 0.9500 . ? C3 C4 1.371(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C7 C8 1.391(2) . ? C7 C12 1.395(2) . ? C8 C9 1.399(3) . ? C8 C13 1.494(3) . ? C9 C10 1.384(3) . ? C9 H9 0.9500 . ? C10 C11 1.361(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 C14 1.504(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C5 N1 C1 116.84(15) . . ? N3 N2 C5 114.10(13) . . ? N3 N2 H2X 108.4 . . ? C5 N2 H2X 111.0 . . ? C6 N3 N2 120.93(13) . . ? C6 N3 H3X 120.5 . . ? N2 N3 H3X 117.7 . . ? C6 N4 C7 123.80(13) . . ? C6 N4 H4X 116.7 . . ? C7 N4 H4X 119.5 . . ? N1 C1 C2 123.65(17) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 118.56(17) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.01(17) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 118.50(16) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 123.38(16) . . ? N1 C5 N2 114.65(14) . . ? C4 C5 N2 121.95(15) . . ? N4 C6 N3 117.07(14) . . ? N4 C6 S1 123.58(12) . . ? N3 C6 S1 119.35(12) . . ? C8 C7 C12 122.32(15) . . ? C8 C7 N4 119.10(14) . . ? C12 C7 N4 118.57(14) . . ? C7 C8 C9 117.22(17) . . ? C7 C8 C13 121.14(16) . . ? C9 C8 C13 121.64(18) . . ? C10 C9 C8 120.70(19) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.56(18) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 121.06(19) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 118.13(18) . . ? C11 C12 C14 121.09(17) . . ? C7 C12 C14 120.75(15) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C6 119.00(16) . . . . ? C5 N1 C1 C2 -0.4(3) . . . . ? N1 C1 C2 C3 -1.6(3) . . . . ? C1 C2 C3 C4 1.6(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C1 N1 C5 C4 2.5(2) . . . . ? C1 N1 C5 N2 -179.13(14) . . . . ? C3 C4 C5 N1 -2.5(2) . . . . ? C3 C4 C5 N2 179.25(15) . . . . ? N3 N2 C5 N1 145.78(13) . . . . ? N3 N2 C5 C4 -35.9(2) . . . . ? C7 N4 C6 N3 -177.48(15) . . . . ? C7 N4 C6 S1 2.9(2) . . . . ? N2 N3 C6 N4 -0.7(2) . . . . ? N2 N3 C6 S1 178.91(12) . . . . ? C6 N4 C7 C8 -98.22(19) . . . . ? C6 N4 C7 C12 82.2(2) . . . . ? C12 C7 C8 C9 0.3(2) . . . . ? N4 C7 C8 C9 -179.23(14) . . . . ? C12 C7 C8 C13 -179.35(16) . . . . ? N4 C7 C8 C13 1.1(2) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C13 C8 C9 C10 179.03(18) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C10 C11 C12 C14 -178.33(18) . . . . ? C8 C7 C12 C11 0.1(2) . . . . ? N4 C7 C12 C11 179.67(15) . . . . ? C8 C7 C12 C14 178.21(16) . . . . ? N4 C7 C12 C14 -2.2(2) . . . . ? 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 H2X S1 0.90 2.44 3.3013(14) 161.0 6_556 N3 H3X N1 0.89 2.08 2.9721(19) 172.6 6_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.310 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.039 data_kp69 _database_code_depnum_ccdc_archive 'CCDC 906517' #TrackingRef 'KP69.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N5 S' _chemical_formula_weight 245.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.6280(17) _cell_length_b 14.716(3) _cell_length_c 9.834(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.82(3) _cell_angle_gamma 90.00 _cell_volume 1159.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4680 _cell_measurement_theta_min 2.2308 _cell_measurement_theta_max 31.1378 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7363 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8636 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3639 _reflns_number_gt 3620 _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^)+(0.0280P)^2^+0.3641P] 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 0.60(5) _refine_ls_number_reflns 3639 _refine_ls_number_parameters 328 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0240 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0596 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.53606(5) 0.75112(3) 0.67814(5) 0.02358(11) Uani 1 1 d . . . N1 N 1.01945(19) 0.83192(12) 1.28200(17) 0.0230(4) Uani 1 1 d . . . N2 N 0.78401(19) 0.84671(13) 1.07260(17) 0.0205(3) Uani 1 1 d . . . H2X H 0.774(3) 0.9017(18) 1.098(2) 0.026(6) Uiso 1 1 d . . . N3 N 0.7169(2) 0.83596(12) 0.92079(17) 0.0228(4) Uani 1 1 d . . . H3X H 0.779(3) 0.8603(16) 0.867(2) 0.033(6) Uiso 1 1 d . . . N4 N 0.50802(19) 0.74727(13) 0.94037(16) 0.0226(3) Uani 1 1 d . . . H4X H 0.5329 0.7668 1.0318 0.050 Uiso 1 1 d . . . N5 N 0.2476(2) 0.54088(12) 0.86578(18) 0.0251(4) Uani 1 1 d . . . C1 C 1.1573(2) 0.78396(17) 1.3612(2) 0.0299(5) Uani 1 1 d . . . H1 H 1.2199 0.8040 1.4581 0.036 Uiso 1 1 calc R . . C2 C 1.2126(3) 0.70894(17) 1.3117(2) 0.0322(5) Uani 1 1 d . . . H2 H 1.3104 0.6779 1.3723 0.039 Uiso 1 1 calc R . . C3 C 1.1229(3) 0.67906(16) 1.1711(2) 0.0305(5) Uani 1 1 d . . . H3 H 1.1593 0.6276 1.1328 0.037 Uiso 1 1 calc R . . C4 C 0.9800(2) 0.72465(14) 1.0869(2) 0.0250(4) Uani 1 1 d . . . H4 H 0.9157 0.7050 0.9903 0.030 Uiso 1 1 calc R . . C5 C 0.9322(2) 0.80060(13) 1.1473(2) 0.0201(4) Uani 1 1 d . . . C6 C 0.5886(2) 0.77853(13) 0.8569(2) 0.0201(4) Uani 1 1 d . . . C7 C 0.3635(2) 0.69021(14) 0.88394(19) 0.0201(4) Uani 1 1 d . . . C8 C 0.2072(2) 0.72610(14) 0.8059(2) 0.0275(5) Uani 1 1 d . . . H8 H 0.1934 0.7893 0.7853 0.033 Uiso 1 1 calc R . . C9 C 0.0717(3) 0.66802(15) 0.7588(2) 0.0300(5) Uani 1 1 d . . . H9 H -0.0372 0.6905 0.7049 0.036 Uiso 1 1 calc R . . C10 C 0.0975(3) 0.57717(16) 0.7913(2) 0.0258(5) Uani 1 1 d . . . H10 H 0.0035 0.5378 0.7591 0.031 Uiso 1 1 calc R . . C11 C 0.3788(2) 0.59835(14) 0.9111(2) 0.0230(4) Uani 1 1 d . . . H11 H 0.4866 0.5742 0.9642 0.028 Uiso 1 1 calc R . . S21 S 0.03635(6) 0.44151(3) 0.21198(5) 0.02500(12) Uani 1 1 d . . . N21 N 0.52169(19) 0.35595(13) 0.81570(17) 0.0247(4) Uani 1 1 d . . . N22 N 0.2797(2) 0.34882(13) 0.60924(17) 0.0223(4) Uani 1 1 d . . . H22X H 0.267(3) 0.287(2) 0.635(3) 0.058(9) Uiso 1 1 d . . . N23 N 0.2156(2) 0.35942(12) 0.45730(18) 0.0235(4) Uani 1 1 d . . . H23X H 0.274(3) 0.3459(18) 0.407(3) 0.034(7) Uiso 1 1 d . . . N24 N -0.00332(19) 0.44237(13) 0.46852(18) 0.0224(3) Uani 1 1 d . . . H24X H 0.019(3) 0.4170(15) 0.553(3) 0.032(6) Uiso 1 1 d . . . N25 N -0.2430(2) 0.65386(12) 0.34616(19) 0.0281(4) Uani 1 1 d . . . C21 C 0.6639(3) 0.39857(17) 0.8935(2) 0.0310(5) Uani 1 1 d . . . H21 H 0.7282 0.3748 0.9875 0.037 Uiso 1 1 calc R . . C22 C 0.7242(3) 0.47456(17) 0.8473(2) 0.0335(5) Uani 1 1 d . . . H22 H 0.8256 0.5025 0.9078 0.040 Uiso 1 1 calc R . . C23 C 0.6325(3) 0.50858(16) 0.7105(2) 0.0306(5) Uani 1 1 d . . . H23 H 0.6713 0.5599 0.6738 0.037 Uiso 1 1 calc R . . C24 C 0.4834(2) 0.46745(15) 0.6270(2) 0.0273(5) Uani 1 1 d . . . H24 H 0.4171 0.4904 0.5330 0.033 Uiso 1 1 calc R . . C25 C 0.4327(2) 0.39127(14) 0.6842(2) 0.0203(4) Uani 1 1 d . . . C26 C 0.0848(2) 0.41406(13) 0.3892(2) 0.0210(4) Uani 1 1 d . . . C27 C -0.1438(2) 0.50195(14) 0.4074(2) 0.0209(4) Uani 1 1 d . . . C28 C -0.3060(2) 0.46945(15) 0.3542(2) 0.0310(5) Uani 1 1 d . . . H28 H -0.3278 0.4064 0.3574 0.037 Uiso 1 1 calc R . . C29 C -0.4359(2) 0.53064(16) 0.2964(2) 0.0320(5) Uani 1 1 d . . . H29 H -0.5485 0.5104 0.2589 0.038 Uiso 1 1 calc R . . C30 C -0.3987(3) 0.62103(16) 0.2942(2) 0.0272(5) Uani 1 1 d . . . H30 H -0.4884 0.6626 0.2537 0.033 Uiso 1 1 calc R . . C31 C -0.1184(2) 0.59421(14) 0.4009(2) 0.0240(4) Uani 1 1 d . . . H31 H -0.0070 0.6164 0.4372 0.029 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 0.0217(2) 0.0274(3) 0.0201(2) -0.0020(2) 0.00599(17) -0.0027(2) N1 0.0170(8) 0.0297(10) 0.0213(9) -0.0047(7) 0.0060(6) -0.0011(7) N2 0.0192(8) 0.0228(10) 0.0174(9) -0.0024(7) 0.0044(6) -0.0003(7) N3 0.0194(8) 0.0289(10) 0.0181(9) 0.0011(7) 0.0048(6) -0.0040(7) N4 0.0228(8) 0.0255(9) 0.0189(8) -0.0035(7) 0.0068(6) -0.0072(8) N5 0.0281(9) 0.0222(10) 0.0255(9) -0.0017(7) 0.0105(7) -0.0042(7) C1 0.0205(10) 0.0432(14) 0.0221(11) -0.0039(9) 0.0033(8) -0.0009(9) C2 0.0245(11) 0.0428(14) 0.0290(12) 0.0040(10) 0.0095(9) 0.0085(10) C3 0.0312(11) 0.0293(12) 0.0349(13) -0.0005(9) 0.0169(9) 0.0033(9) C4 0.0229(10) 0.0275(12) 0.0247(11) -0.0052(8) 0.0090(8) -0.0024(8) C5 0.0159(9) 0.0240(11) 0.0204(10) 0.0008(8) 0.0068(7) -0.0049(8) C6 0.0174(9) 0.0178(10) 0.0219(10) 0.0020(7) 0.0037(7) 0.0020(7) C7 0.0203(9) 0.0250(11) 0.0153(10) -0.0032(7) 0.0071(7) -0.0039(8) C8 0.0260(10) 0.0208(11) 0.0302(11) -0.0015(8) 0.0043(8) 0.0001(8) C9 0.0210(10) 0.0353(13) 0.0287(12) -0.0040(9) 0.0034(8) 0.0027(8) C10 0.0203(10) 0.0327(13) 0.0242(10) -0.0059(9) 0.0083(8) -0.0082(9) C11 0.0211(10) 0.0260(12) 0.0229(11) 0.0013(8) 0.0092(8) 0.0004(8) S21 0.0239(2) 0.0301(3) 0.0203(2) 0.0024(2) 0.00737(18) 0.0062(2) N21 0.0194(8) 0.0324(10) 0.0202(9) 0.0025(7) 0.0052(7) 0.0006(7) N22 0.0196(8) 0.0258(10) 0.0181(9) 0.0026(7) 0.0030(6) 0.0006(7) N23 0.0213(8) 0.0303(10) 0.0182(9) 0.0007(7) 0.0066(7) 0.0057(7) N24 0.0212(8) 0.0256(9) 0.0190(9) 0.0034(7) 0.0060(6) 0.0045(7) N25 0.0269(9) 0.0253(10) 0.0318(10) 0.0028(8) 0.0107(8) 0.0043(8) C21 0.0219(10) 0.0454(14) 0.0228(11) 0.0019(9) 0.0049(8) -0.0060(9) C22 0.0211(10) 0.0436(14) 0.0331(12) -0.0045(10) 0.0069(9) -0.0084(10) C23 0.0260(11) 0.0277(12) 0.0401(13) 0.0034(9) 0.0145(9) -0.0031(9) C24 0.0247(10) 0.0290(12) 0.0274(11) 0.0071(9) 0.0087(8) 0.0045(8) C25 0.0181(9) 0.0221(11) 0.0216(10) 0.0005(8) 0.0085(8) 0.0030(8) C26 0.0186(10) 0.0186(10) 0.0226(10) -0.0024(7) 0.0039(7) -0.0026(7) C27 0.0220(9) 0.0246(11) 0.0172(10) 0.0019(8) 0.0086(8) 0.0046(8) C28 0.0270(10) 0.0245(11) 0.0360(12) 0.0026(9) 0.0052(9) -0.0022(8) C29 0.0173(10) 0.0354(13) 0.0380(13) 0.0062(9) 0.0041(8) 0.0020(8) C30 0.0235(10) 0.0306(13) 0.0282(12) 0.0056(9) 0.0104(8) 0.0073(8) C31 0.0209(10) 0.0254(12) 0.0256(11) -0.0002(8) 0.0084(8) 0.0005(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 C6 1.693(2) . ? N1 C5 1.339(3) . ? N1 C1 1.353(3) . ? N2 C5 1.392(3) . ? N2 N3 1.395(2) . ? N2 H2X 0.86(3) . ? N3 C6 1.348(3) . ? N3 H3X 0.96(2) . ? N4 C6 1.339(2) . ? N4 C7 1.433(2) . ? N4 H4X 0.8907 . ? N5 C10 1.339(3) . ? N5 C11 1.349(3) . ? C1 C2 1.363(3) . ? C1 H1 0.9500 . ? C2 C3 1.382(3) . ? C2 H2 0.9500 . ? C3 C4 1.377(3) . ? C3 H3 0.9500 . ? C4 C5 1.398(3) . ? C4 H4 0.9500 . ? C7 C11 1.375(3) . ? C7 C8 1.385(3) . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 C10 1.374(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? S21 C26 1.684(2) . ? N21 C21 1.337(3) . ? N21 C25 1.339(3) . ? N22 N23 1.396(2) . ? N22 C25 1.397(3) . ? N22 H22X 0.95(3) . ? N23 C26 1.344(3) . ? N23 H23X 0.85(2) . ? N24 C26 1.342(3) . ? N24 C27 1.434(3) . ? N24 H24X 0.86(2) . ? N25 C31 1.336(3) . ? N25 C30 1.338(3) . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 C23 1.376(3) . ? C22 H22 0.9500 . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 C25 1.396(3) . ? C24 H24 0.9500 . ? C27 C31 1.381(3) . ? C27 C28 1.384(3) . ? C28 C29 1.384(3) . ? C28 H28 0.9500 . ? C29 C30 1.370(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? 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 C5 N1 C1 116.15(17) . . ? C5 N2 N3 116.37(16) . . ? C5 N2 H2X 118.5(15) . . ? N3 N2 H2X 112.0(15) . . ? C6 N3 N2 120.84(16) . . ? C6 N3 H3X 120.7(14) . . ? N2 N3 H3X 117.2(14) . . ? C6 N4 C7 122.62(16) . . ? C6 N4 H4X 121.5 . . ? C7 N4 H4X 115.4 . . ? C10 N5 C11 116.90(18) . . ? N1 C1 C2 124.5(2) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 118.4(2) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 118.29(19) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 N2 115.01(17) . . ? N1 C5 C4 123.32(18) . . ? N2 C5 C4 121.60(18) . . ? N4 C6 N3 116.92(17) . . ? N4 C6 S1 123.71(15) . . ? N3 C6 S1 119.36(14) . . ? C11 C7 C8 119.05(18) . . ? C11 C7 N4 119.65(17) . . ? C8 C7 N4 121.27(19) . . ? C9 C8 C7 118.6(2) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C8 118.70(19) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N5 C10 C9 123.77(19) . . ? N5 C10 H10 118.1 . . ? C9 C10 H10 118.1 . . ? N5 C11 C7 123.00(18) . . ? N5 C11 H11 118.5 . . ? C7 C11 H11 118.5 . . ? C21 N21 C25 116.47(19) . . ? N23 N22 C25 115.81(16) . . ? N23 N22 H22X 110.5(17) . . ? C25 N22 H22X 117.3(17) . . ? C26 N23 N22 121.65(17) . . ? C26 N23 H23X 114.7(17) . . ? N22 N23 H23X 120.9(16) . . ? C26 N24 C27 121.30(17) . . ? C26 N24 H24X 116.9(15) . . ? C27 N24 H24X 121.1(15) . . ? C31 N25 C30 117.38(19) . . ? N21 C21 C22 124.7(2) . . ? N21 C21 H21 117.6 . . ? C22 C21 H21 117.6 . . ? C23 C22 C21 117.8(2) . . ? C23 C22 H22 121.1 . . ? C21 C22 H22 121.1 . . ? C22 C23 C24 119.4(2) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C23 C24 C25 118.30(19) . . ? C23 C24 H24 120.9 . . ? C25 C24 H24 120.9 . . ? N21 C25 C24 123.22(19) . . ? N21 C25 N22 115.24(18) . . ? C24 C25 N22 121.49(18) . . ? N24 C26 N23 116.67(18) . . ? N24 C26 S21 123.43(16) . . ? N23 C26 S21 119.88(15) . . ? C31 C27 C28 118.54(18) . . ? C31 C27 N24 119.77(18) . . ? C28 C27 N24 121.68(19) . . ? C29 C28 C27 118.7(2) . . ? C29 C28 H28 120.6 . . ? C27 C28 H28 120.6 . . ? C30 C29 C28 118.64(19) . . ? C30 C29 H29 120.7 . . ? C28 C29 H29 120.7 . . ? N25 C30 C29 123.5(2) . . ? N25 C30 H30 118.2 . . ? C29 C30 H30 118.2 . . ? N25 C31 C27 123.16(19) . . ? N25 C31 H31 118.4 . . ? C27 C31 H31 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C6 101.0(2) . . . . ? C5 N1 C1 C2 1.5(3) . . . . ? N1 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C1 N1 C5 N2 175.05(18) . . . . ? C1 N1 C5 C4 -2.0(3) . . . . ? N3 N2 C5 N1 160.87(17) . . . . ? N3 N2 C5 C4 -22.1(3) . . . . ? C3 C4 C5 N1 0.9(3) . . . . ? C3 C4 C5 N2 -175.88(18) . . . . ? C7 N4 C6 N3 176.18(17) . . . . ? C7 N4 C6 S1 -2.8(3) . . . . ? N2 N3 C6 N4 13.2(3) . . . . ? N2 N3 C6 S1 -167.73(14) . . . . ? C6 N4 C7 C11 102.3(2) . . . . ? C6 N4 C7 C8 -79.6(2) . . . . ? C11 C7 C8 C9 0.3(3) . . . . ? N4 C7 C8 C9 -177.74(18) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C11 N5 C10 C9 0.4(3) . . . . ? C8 C9 C10 N5 -0.5(3) . . . . ? C10 N5 C11 C7 0.0(3) . . . . ? C8 C7 C11 N5 -0.4(3) . . . . ? N4 C7 C11 N5 177.73(16) . . . . ? C25 N22 N23 C26 -106.7(2) . . . . ? C25 N21 C21 C22 -0.6(3) . . . . ? N21 C21 C22 C23 -0.7(4) . . . . ? C21 C22 C23 C24 1.6(3) . . . . ? C22 C23 C24 C25 -1.1(3) . . . . ? C21 N21 C25 C24 1.1(3) . . . . ? C21 N21 C25 N22 -176.17(18) . . . . ? C23 C24 C25 N21 -0.3(3) . . . . ? C23 C24 C25 N22 176.85(18) . . . . ? N23 N22 C25 N21 -156.70(17) . . . . ? N23 N22 C25 C24 26.0(3) . . . . ? C27 N24 C26 N23 179.05(18) . . . . ? C27 N24 C26 S21 -2.4(3) . . . . ? N22 N23 C26 N24 -13.8(3) . . . . ? N22 N23 C26 S21 167.56(15) . . . . ? C26 N24 C27 C31 -81.2(2) . . . . ? C26 N24 C27 C28 98.9(2) . . . . ? C31 C27 C28 C29 0.2(3) . . . . ? N24 C27 C28 C29 -179.87(18) . . . . ? C27 C28 C29 C30 -0.1(3) . . . . ? C31 N25 C30 C29 0.9(3) . . . . ? C28 C29 C30 N25 -0.5(3) . . . . ? C30 N25 C31 C27 -0.8(3) . . . . ? C28 C27 C31 N25 0.2(3) . . . . ? N24 C27 C31 N25 -179.70(17) . . . . ? 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 H2X N5 0.86(3) 2.10(3) 2.955(3) 172(2) 2_657 N3 H3X S21 0.96(2) 2.34(2) 3.2739(18) 165.5(19) 2_656 N4 H4X N21 0.89 2.17 2.972(2) 149.2 2_657 N22 H22X N25 0.95(3) 1.99(3) 2.937(3) 170(2) 2_546 N23 H23X S1 0.85(2) 2.52(3) 3.3205(18) 157(2) 2_646 N24 H24X N1 0.86(2) 2.17(2) 2.989(2) 158(2) 2_647 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.181 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.032 data_kp2 _database_code_depnum_ccdc_archive 'CCDC 906518' #TrackingRef 'kp2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N5 O2 S' _chemical_formula_weight 289.32 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 Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 7.0476(14) _cell_length_b 9.2828(19) _cell_length_c 10.069(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.45(3) _cell_angle_gamma 90.00 _cell_volume 634.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 106(2) _cell_measurement_reflns_used 2227 _cell_measurement_theta_min 2.0971 _cell_measurement_theta_max 31.2136 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7332 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 106(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 'Rigaku Saturn 724' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4606 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 24.47 _reflns_number_total 1903 _reflns_number_gt 1901 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0328P)^2^+0.1455P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 1903 _refine_ls_number_parameters 181 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0193 _refine_ls_R_factor_gt 0.0193 _refine_ls_wR_factor_ref 0.0516 _refine_ls_wR_factor_gt 0.0516 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.051 _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 0.85360(5) 0.30225(4) 0.00792(4) 0.01716(11) Uani 1 1 d . . . O1 O 0.1382(2) -0.20323(14) 0.24901(13) 0.0293(3) Uani 1 1 d . . . O2 O 0.02483(16) -0.10839(13) 0.04682(13) 0.0266(3) Uani 1 1 d . . . N1 N 1.3170(2) 0.45994(14) 0.59983(14) 0.0171(3) Uani 1 1 d . . . N2 N 1.08583(19) 0.41933(14) 0.39302(14) 0.0162(3) Uani 1 1 d . . . H2X H 1.0196 0.4943 0.4150 0.019 Uiso 1 1 d . . . N3 N 1.05218(19) 0.40133(15) 0.25048(13) 0.0151(3) Uani 1 1 d . . . H3X H 1.1236 0.4443 0.2136 0.018 Uiso 1 1 d . . . N4 N 0.8264(2) 0.22944(15) 0.26092(13) 0.0171(3) Uani 1 1 d . . . H4X H 0.8840 0.2280 0.3499 0.021 Uiso 1 1 d . . . N5 N 0.1521(2) -0.12039(15) 0.15714(14) 0.0186(3) Uani 1 1 d . . . C1 C 1.4977(2) 0.43953(17) 0.68506(17) 0.0191(4) Uani 1 1 d . . . H1 H 1.5283 0.4854 0.7726 0.023 Uiso 1 1 calc R . . C2 C 1.6403(2) 0.35635(18) 0.65298(17) 0.0185(3) Uani 1 1 d . . . H2 H 1.7676 0.3476 0.7150 0.022 Uiso 1 1 calc R . . C3 C 1.5929(3) 0.28569(18) 0.52753(18) 0.0188(4) Uani 1 1 d . . . H3 H 1.6868 0.2247 0.5034 0.023 Uiso 1 1 calc R . . C4 C 1.4079(3) 0.30391(18) 0.43684(17) 0.0176(4) Uani 1 1 d . . . H4 H 1.3724 0.2557 0.3505 0.021 Uiso 1 1 calc R . . C5 C 1.2761(2) 0.39519(16) 0.47664(15) 0.0137(3) Uani 1 1 d . . . C6 C 0.9102(2) 0.31130(16) 0.18078(16) 0.0139(3) Uani 1 1 d . . . C7 C 0.6596(2) 0.13921(17) 0.22239(16) 0.0144(3) Uani 1 1 d . . . C8 C 0.4916(2) 0.17432(17) 0.11759(16) 0.0164(4) Uani 1 1 d . . . H8 H 0.4917 0.2574 0.0625 0.020 Uiso 1 1 calc R . . C9 C 0.3254(2) 0.08874(18) 0.09381(16) 0.0161(3) Uani 1 1 d . . . H9 H 0.2119 0.1106 0.0213 0.019 Uiso 1 1 calc R . . C10 C 0.3281(2) -0.03014(18) 0.17854(16) 0.0156(3) Uani 1 1 d . . . C11 C 0.4928(2) -0.06705(17) 0.28284(16) 0.0168(3) Uani 1 1 d . . . H11 H 0.4909 -0.1486 0.3395 0.020 Uiso 1 1 calc R . . C12 C 0.6594(2) 0.01673(17) 0.30292(16) 0.0161(3) Uani 1 1 d . . . H12 H 0.7750 -0.0090 0.3720 0.019 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 0.0180(2) 0.02225(19) 0.00960(18) -0.00086(15) 0.00079(14) -0.00392(16) O1 0.0266(7) 0.0354(7) 0.0243(7) 0.0046(6) 0.0037(6) -0.0123(6) O2 0.0168(7) 0.0307(7) 0.0255(7) -0.0024(5) -0.0062(5) -0.0043(5) N1 0.0176(7) 0.0191(7) 0.0126(7) -0.0019(6) 0.0003(5) 0.0018(5) N2 0.0154(7) 0.0209(7) 0.0108(6) -0.0029(5) 0.0010(5) 0.0017(6) N3 0.0132(7) 0.0215(7) 0.0095(6) 0.0007(5) 0.0010(5) -0.0036(5) N4 0.0163(7) 0.0232(7) 0.0096(7) 0.0008(5) -0.0004(5) -0.0040(6) N5 0.0152(7) 0.0208(7) 0.0182(7) -0.0044(6) 0.0020(6) 0.0000(6) C1 0.0202(9) 0.0202(8) 0.0133(8) -0.0030(6) -0.0016(7) -0.0009(7) C2 0.0140(8) 0.0205(8) 0.0177(8) 0.0032(7) -0.0012(6) -0.0007(7) C3 0.0157(9) 0.0248(9) 0.0166(8) 0.0016(7) 0.0055(7) 0.0032(7) C4 0.0187(9) 0.0233(9) 0.0103(8) -0.0014(6) 0.0029(7) 0.0007(6) C5 0.0140(8) 0.0152(7) 0.0111(7) 0.0014(6) 0.0015(6) -0.0032(6) C6 0.0114(8) 0.0149(8) 0.0146(8) -0.0003(5) 0.0023(6) 0.0025(6) C7 0.0119(8) 0.0188(7) 0.0124(7) -0.0044(6) 0.0030(6) -0.0010(6) C8 0.0192(9) 0.0170(8) 0.0129(8) 0.0006(6) 0.0042(7) 0.0025(6) C9 0.0120(8) 0.0223(8) 0.0127(8) -0.0027(6) 0.0009(6) 0.0033(6) C10 0.0138(8) 0.0195(8) 0.0134(8) -0.0055(6) 0.0031(6) -0.0021(6) C11 0.0183(8) 0.0181(8) 0.0128(8) -0.0021(6) 0.0018(6) -0.0010(7) C12 0.0143(8) 0.0216(8) 0.0102(7) -0.0011(6) -0.0008(6) 0.0005(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 C6 1.6809(17) . ? O1 N5 1.2267(19) . ? O2 N5 1.2328(18) . ? N1 C5 1.339(2) . ? N1 C1 1.346(2) . ? N2 C5 1.398(2) . ? N2 N3 1.4010(19) . ? N2 H2X 0.8979 . ? N3 C6 1.348(2) . ? N3 H3X 0.8062 . ? N4 C6 1.354(2) . ? N4 C7 1.411(2) . ? N4 H4X 0.8798 . ? N5 C10 1.465(2) . ? C1 C2 1.373(3) . ? C1 H1 0.9500 . ? C2 C3 1.383(2) . ? C2 H2 0.9500 . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C7 C12 1.397(2) . ? C7 C8 1.399(2) . ? C8 C9 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.392(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C11 C12 1.378(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 C5 N1 C1 117.47(14) . . ? C5 N2 N3 118.11(13) . . ? C5 N2 H2X 117.0 . . ? N3 N2 H2X 112.8 . . ? C6 N3 N2 120.46(13) . . ? C6 N3 H3X 122.3 . . ? N2 N3 H3X 117.2 . . ? C6 N4 C7 129.31(13) . . ? C6 N4 H4X 117.3 . . ? C7 N4 H4X 113.3 . . ? O1 N5 O2 123.45(14) . . ? O1 N5 C10 118.82(13) . . ? O2 N5 C10 117.73(13) . . ? N1 C1 C2 123.84(15) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 117.88(15) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C2 C3 C4 119.94(16) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 117.79(15) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N1 C5 C4 122.97(15) . . ? N1 C5 N2 114.91(14) . . ? C4 C5 N2 122.03(14) . . ? N3 C6 N4 114.77(14) . . ? N3 C6 S1 120.57(12) . . ? N4 C6 S1 124.63(12) . . ? C12 C7 C8 119.75(14) . . ? C12 C7 N4 116.94(13) . . ? C8 C7 N4 123.03(14) . . ? C9 C8 C7 120.32(14) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 118.47(14) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C11 C10 C9 122.21(15) . . ? C11 C10 N5 118.42(15) . . ? C9 C10 N5 119.37(13) . . ? C12 C11 C10 118.75(15) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C11 C12 C7 120.45(14) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N2 N3 C6 124.87(15) . . . . ? C5 N1 C1 C2 -0.3(2) . . . . ? N1 C1 C2 C3 -2.3(3) . . . . ? C1 C2 C3 C4 2.1(2) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C1 N1 C5 C4 3.0(2) . . . . ? C1 N1 C5 N2 179.51(14) . . . . ? C3 C4 C5 N1 -3.1(2) . . . . ? C3 C4 C5 N2 -179.36(14) . . . . ? N3 N2 C5 N1 157.69(13) . . . . ? N3 N2 C5 C4 -25.8(2) . . . . ? N2 N3 C6 N4 -8.3(2) . . . . ? N2 N3 C6 S1 173.63(11) . . . . ? C7 N4 C6 N3 171.02(15) . . . . ? C7 N4 C6 S1 -11.0(2) . . . . ? C6 N4 C7 C12 147.87(16) . . . . ? C6 N4 C7 C8 -38.3(2) . . . . ? C12 C7 C8 C9 0.3(2) . . . . ? N4 C7 C8 C9 -173.45(15) . . . . ? C7 C8 C9 C10 1.6(2) . . . . ? C8 C9 C10 C11 -1.7(2) . . . . ? C8 C9 C10 N5 178.63(15) . . . . ? O1 N5 C10 C11 16.8(2) . . . . ? O2 N5 C10 C11 -163.33(14) . . . . ? O1 N5 C10 C9 -163.45(15) . . . . ? O2 N5 C10 C9 16.4(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? N5 C10 C11 C12 179.52(14) . . . . ? C10 C11 C12 C7 2.1(2) . . . . ? C8 C7 C12 C11 -2.2(2) . . . . ? N4 C7 C12 C11 171.92(15) . . . . ? 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 H2X S1 0.90 2.53 3.4214(15) 172.8 2_565 N3 H3X N1 0.81 2.19 2.992(2) 173.8 2_564 N4 H4X O2 0.88 2.26 3.0595(19) 151.3 2_655 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.47 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.126 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.031