# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- all cif.cif' _publ_contact_author_name 'Dr. Gopal Das' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_contact_author_email gdas@iitg.ernet.in _publ_contact_author_phone 00913612582313 _publ_contact_author_fax 00913612582349 loop_ _publ_author_name _publ_author_address A.Basu ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; G.Das '' data_Complex1 _database_code_depnum_ccdc_archive 'CCDC 814617' #TrackingRef '- all cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N7 O6 S' _chemical_formula_weight 511.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1908(5) _cell_length_b 11.6347(6) _cell_length_c 12.4736(7) _cell_angle_alpha 100.591(4) _cell_angle_beta 111.361(3) _cell_angle_gamma 101.380(4) _cell_volume 1169.06(11) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2188 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 19.75 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16139 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.1614 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.40 _reflns_number_total 5875 _reflns_number_gt 5752 _reflns_threshold_expression >2\s(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, 2008)' _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^ > 2\s(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^)+(0.0549P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5664 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1670 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1406 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0.002 _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 0.33901(11) 0.04629(8) 0.06671(7) 0.0651(3) Uani 1 1 d . . . C9 C 0.5334(3) 0.2125(3) 0.4907(3) 0.0390(8) Uani 1 1 d . . . C1 C 0.4670(3) 0.1811(3) 0.3628(3) 0.0424(8) Uani 1 1 d . . . C2 C 0.3654(4) 0.2413(3) 0.3022(3) 0.0551(9) Uani 1 1 d D . . H2 H 0.3239 0.2213 0.2189 0.066 Uiso 1 1 calc RD . . C8 C 0.6373(3) 0.1553(3) 0.5614(3) 0.0474(9) Uani 1 1 d D . . H8 H 0.6637 0.0912 0.5235 0.057 Uiso 1 1 calc RD . . C10 C 0.4921(4) 0.3087(3) 0.5514(3) 0.0453(8) Uani 1 1 d . . . C3 C 0.3234(4) 0.3330(3) 0.3646(4) 0.0604(10) Uani 1 1 d D . . H3 H 0.2511 0.3711 0.3222 0.073 Uiso 1 1 calc RD . . C6 C 0.6618(4) 0.2873(3) 0.7428(3) 0.0645(10) Uani 1 1 d D . . H6 H 0.7052 0.3121 0.8261 0.077 Uiso 1 1 calc RD . . C7 C 0.7005(4) 0.1907(3) 0.6838(3) 0.0576(10) Uani 1 1 d D . . H7 H 0.7689 0.1511 0.7279 0.069 Uiso 1 1 calc RD . . C4 C 0.3867(4) 0.3666(3) 0.4855(3) 0.0568(10) Uani 1 1 d D . . H4 H 0.3597 0.4290 0.5254 0.068 Uiso 1 1 calc RD . . C5 C 0.5617(4) 0.3441(3) 0.6787(3) 0.0611(10) Uani 1 1 d D . . H5 H 0.5375 0.4081 0.7190 0.073 Uiso 1 1 calc RD . . C12 C 0.7187(3) -0.1663(3) 0.2563(3) 0.0399(8) Uani 1 1 d . . . C13 C 0.8336(3) -0.1924(3) 0.3635(3) 0.0395(8) Uani 1 1 d . . . C17 C 1.0081(4) -0.3105(3) 0.4476(3) 0.0464(8) Uani 1 1 d . . . C18 C 0.9044(3) -0.2843(3) 0.3481(3) 0.0443(8) Uani 1 1 d D . . H18 H 0.8831 -0.3288 0.2713 0.053 Uiso 1 1 calc RD . . C11 C 0.4769(3) 0.0298(3) 0.1921(3) 0.0421(8) Uani 1 1 d . . . C14 C 0.8682(3) -0.1277(3) 0.4803(3) 0.0416(8) Uani 1 1 d D . . H14 H 0.8221 -0.0650 0.4930 0.050 Uiso 1 1 calc RD . . C15 C 0.9704(4) -0.1570(3) 0.5761(3) 0.0429(8) Uani 1 1 d . . . C16 C 1.0425(3) -0.2477(3) 0.5628(3) 0.0494(9) Uani 1 1 d D . . H16 H 1.1118 -0.2660 0.6287 0.059 Uiso 1 1 calc RD . . N3 N 0.6668(3) -0.0725(2) 0.28270(19) 0.0436(7) Uani 1 1 d . . . N2 N 0.5559(3) -0.0541(2) 0.1809(2) 0.0479(7) Uani 1 1 d D . . N1 N 0.5180(3) 0.0902(2) 0.3076(2) 0.0493(7) Uani 1 1 d D . . N4 N 0.9985(4) -0.0911(3) 0.6966(3) 0.0594(8) Uani 1 1 d . . . N5 N 1.0811(4) -0.4111(3) 0.4276(3) 0.0627(9) Uani 1 1 d . . . O1 O 0.6791(2) -0.23471(18) 0.15167(17) 0.0522(6) Uani 1 1 d . . . O3 O 1.0783(3) -0.1243(2) 0.7808(2) 0.0895(9) Uani 1 1 d . . . O4 O 1.1741(3) -0.4301(2) 0.5182(2) 0.0831(8) Uani 1 1 d . . . O2 O 0.9421(3) -0.0055(2) 0.70852(19) 0.0723(8) Uani 1 1 d . . . O5 O 1.0448(3) -0.4687(2) 0.3255(3) 0.0879(9) Uani 1 1 d . . . N7 N 1.0531(4) 0.7661(5) 0.9780(3) 0.0867(12) Uani 1 1 d D . . H7N H 1.1333 0.8042 0.9659 0.104 Uiso 1 1 calc RD . . C19 C 0.9835(6) 0.8176(4) 1.0390(3) 0.0676(11) Uani 1 1 d D . . H19 H 1.0111 0.9009 1.0749 0.081 Uiso 1 1 calc RD . . C21 C 0.8644(5) 0.6247(4) 0.9786(4) 0.0768(12) Uani 1 1 d D . . H21 H 0.7938 0.5494 0.9662 0.092 Uiso 1 1 calc RD . . N6 N 0.8690(4) 0.7339(3) 1.0417(2) 0.0549(8) Uani 1 1 d D . . C20 C 0.9819(7) 0.6448(6) 0.9364(4) 0.0926(16) Uani 1 1 d D . . O6 O 0.3641(4) 0.6362(4) 0.9776(3) 0.1602(16) Uani 1 1 d . . . H6O H 0.4461 0.6265 1.0259 0.240 Uiso 1 1 calc R . . C22 C 0.3722(6) 0.6227(6) 0.8684(4) 0.195(3) Uani 1 1 d D . . H22A H 0.3648 0.6957 0.8440 0.293 Uiso 1 1 calc RD . . H22B H 0.2836 0.5548 0.8099 0.293 Uiso 1 1 calc RD . . H22C H 0.4740 0.6082 0.8749 0.293 Uiso 1 1 calc RD . . H1N H 0.597(3) 0.056(2) 0.354(2) 0.051(9) Uiso 1 1 d D . . H2N H 0.562(5) -0.098(3) 0.106(2) 0.139(17) Uiso 1 1 d D . . H20 H 1.005(5) 0.572(3) 0.890(4) 0.17(2) Uiso 1 1 d D . . H6N H 0.793(4) 0.744(3) 1.086(3) 0.131(16) Uiso 1 1 d 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 0.0630(6) 0.0877(8) 0.0425(5) 0.0251(5) 0.0086(4) 0.0369(5) C9 0.0381(19) 0.034(2) 0.0423(19) 0.0086(16) 0.0153(15) 0.0097(16) C1 0.041(2) 0.040(2) 0.044(2) 0.0097(17) 0.0141(16) 0.0172(17) C2 0.054(2) 0.051(2) 0.054(2) 0.0154(19) 0.0124(18) 0.0217(19) C8 0.051(2) 0.051(2) 0.040(2) 0.0087(17) 0.0155(16) 0.0223(17) C10 0.041(2) 0.043(2) 0.055(2) 0.0124(19) 0.0231(18) 0.0109(17) C3 0.055(2) 0.056(3) 0.075(3) 0.024(2) 0.022(2) 0.028(2) C6 0.069(3) 0.071(3) 0.045(2) 0.004(2) 0.022(2) 0.016(2) C7 0.059(2) 0.068(3) 0.045(2) 0.016(2) 0.0175(18) 0.026(2) C4 0.056(2) 0.040(2) 0.081(3) 0.015(2) 0.034(2) 0.0174(19) C5 0.066(3) 0.053(3) 0.063(3) 0.005(2) 0.033(2) 0.016(2) C12 0.0403(19) 0.043(2) 0.037(2) 0.0098(17) 0.0164(16) 0.0138(17) C13 0.0394(19) 0.040(2) 0.0376(19) 0.0093(16) 0.0134(15) 0.0140(16) C17 0.041(2) 0.039(2) 0.065(2) 0.0233(19) 0.0223(18) 0.0150(17) C18 0.045(2) 0.044(2) 0.0435(19) 0.0133(17) 0.0162(16) 0.0143(17) C11 0.046(2) 0.044(2) 0.0357(19) 0.0157(17) 0.0130(16) 0.0140(17) C14 0.043(2) 0.038(2) 0.041(2) 0.0108(16) 0.0138(16) 0.0129(16) C15 0.043(2) 0.043(2) 0.036(2) 0.0118(17) 0.0104(16) 0.0073(17) C16 0.042(2) 0.054(2) 0.046(2) 0.0246(19) 0.0087(16) 0.0114(18) N3 0.0467(17) 0.0513(18) 0.0288(14) 0.0125(13) 0.0067(12) 0.0219(14) N2 0.0528(18) 0.059(2) 0.0361(16) 0.0168(15) 0.0141(14) 0.0309(16) N1 0.0563(19) 0.0535(19) 0.0369(16) 0.0128(15) 0.0100(14) 0.0315(16) N4 0.062(2) 0.065(2) 0.0376(19) 0.0117(19) 0.0137(16) 0.0054(18) N5 0.049(2) 0.053(2) 0.096(3) 0.032(2) 0.031(2) 0.0248(17) O1 0.0610(15) 0.0600(16) 0.0337(13) 0.0038(11) 0.0176(11) 0.0263(12) O3 0.101(2) 0.108(2) 0.0388(14) 0.0316(15) 0.0051(14) 0.0206(17) O4 0.0654(18) 0.0872(19) 0.113(2) 0.0553(17) 0.0308(16) 0.0445(15) O2 0.0827(19) 0.081(2) 0.0468(15) 0.0046(14) 0.0265(13) 0.0221(16) O5 0.106(2) 0.070(2) 0.099(2) 0.0146(17) 0.0482(19) 0.0499(16) N7 0.069(3) 0.149(4) 0.067(2) 0.052(3) 0.038(2) 0.045(3) C19 0.073(3) 0.075(3) 0.052(3) 0.022(2) 0.013(2) 0.033(3) C21 0.083(3) 0.071(3) 0.066(3) 0.008(2) 0.020(2) 0.032(3) N6 0.060(2) 0.064(2) 0.0450(18) 0.0164(18) 0.0208(17) 0.028(2) C20 0.108(4) 0.111(5) 0.063(3) 0.005(3) 0.035(3) 0.062(4) O6 0.100(3) 0.215(4) 0.102(3) -0.019(3) 0.040(2) -0.029(3) C22 0.139(5) 0.280(7) 0.067(3) -0.024(4) 0.044(3) -0.084(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.689(3) . ? C9 C8 1.410(4) . ? C9 C10 1.426(4) . ? C9 C1 1.429(4) . ? C1 C2 1.369(4) . ? C1 N1 1.405(3) . ? C2 C3 1.404(4) . ? C8 C7 1.366(4) . ? C10 C4 1.396(4) . ? C10 C5 1.420(4) . ? C3 C4 1.348(4) . ? C6 C5 1.349(4) . ? C6 C7 1.406(4) . ? C12 O1 1.275(3) . ? C12 N3 1.310(3) . ? C12 C13 1.498(4) . ? C13 C18 1.377(4) . ? C13 C14 1.398(3) . ? C17 C16 1.374(4) . ? C17 C18 1.390(4) . ? C17 N5 1.486(4) . ? C11 N2 1.343(4) . ? C11 N1 1.356(3) . ? C14 C15 1.373(4) . ? C15 C16 1.368(4) . ? C15 N4 1.460(4) . ? N3 N2 1.392(3) . ? N4 O2 1.219(3) . ? N4 O3 1.222(3) . ? N5 O5 1.214(3) . ? N5 O4 1.232(3) . ? N7 C19 1.297(4) . ? N7 C20 1.345(5) . ? C19 N6 1.300(4) . ? C21 N6 1.350(4) . ? C21 C20 1.364(5) . ? O6 C22 1.373(5) . ? 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 C8 C9 C10 117.6(3) . . ? C8 C9 C1 124.6(3) . . ? C10 C9 C1 117.8(3) . . ? C2 C1 N1 124.2(3) . . ? C2 C1 C9 120.1(3) . . ? N1 C1 C9 115.7(3) . . ? C1 C2 C3 120.5(3) . . ? C7 C8 C9 122.2(3) . . ? C4 C10 C5 121.5(3) . . ? C4 C10 C9 119.9(3) . . ? C5 C10 C9 118.6(3) . . ? C4 C3 C2 120.8(3) . . ? C5 C6 C7 120.1(3) . . ? C8 C7 C6 119.7(3) . . ? C3 C4 C10 120.8(3) . . ? C6 C5 C10 121.8(3) . . ? O1 C12 N3 126.6(3) . . ? O1 C12 C13 119.6(3) . . ? N3 C12 C13 113.9(3) . . ? C18 C13 C14 118.5(3) . . ? C18 C13 C12 119.8(3) . . ? C14 C13 C12 121.7(3) . . ? C16 C17 C18 122.1(3) . . ? C16 C17 N5 119.5(3) . . ? C18 C17 N5 118.4(3) . . ? C13 C18 C17 119.9(3) . . ? N2 C11 N1 113.5(3) . . ? N2 C11 S1 118.7(2) . . ? N1 C11 S1 127.8(3) . . ? C15 C14 C13 119.8(3) . . ? C16 C15 C14 122.7(3) . . ? C16 C15 N4 118.9(3) . . ? C14 C15 N4 118.3(3) . . ? C15 C16 C17 117.1(3) . . ? C12 N3 N2 112.0(2) . . ? C11 N2 N3 120.1(3) . . ? C11 N1 C1 134.1(3) . . ? O2 N4 O3 123.2(3) . . ? O2 N4 C15 118.7(3) . . ? O3 N4 C15 118.1(3) . . ? O5 N5 O4 124.9(3) . . ? O5 N5 C17 118.7(3) . . ? O4 N5 C17 116.4(3) . . ? C19 N7 C20 110.4(4) . . ? N7 C19 N6 109.0(4) . . ? N6 C21 C20 107.6(4) . . ? C19 N6 C21 108.2(3) . . ? N7 C20 C21 104.8(4) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.665 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 data_Complex2 _database_code_depnum_ccdc_archive 'CCDC 818087' #TrackingRef '- all cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H27 N9 O6 S' _chemical_formula_weight 569.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.3350(7) _cell_length_b 12.3287(10) _cell_length_c 25.638(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.345(7) _cell_angle_gamma 90.00 _cell_volume 2591.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6515 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 18.81 _exptl_crystal_description block _exptl_crystal_colour ' red ' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 24884 _diffrn_reflns_av_R_equivalents 0.1278 _diffrn_reflns_av_sigmaI/netI 0.1189 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.42 _reflns_number_total 6440 _reflns_number_gt 6410 _reflns_threshold_expression >2\s(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^ > 2\s(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^)+(0.0000P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6141 _refine_ls_number_parameters 361 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.06216(11) 0.47021(8) 0.69313(4) 0.0791(3) Uani 1 1 d . . . O1 O 0.1798(2) 0.22040(17) 0.57609(8) 0.0599(6) Uani 1 1 d . . . O2 O 0.4056(3) 0.0430(2) 0.43611(12) 0.0998(9) Uani 1 1 d . . . O3 O 0.4906(3) 0.1366(2) 0.37538(12) 0.0952(9) Uani 1 1 d . . . O5 O 0.3479(3) 0.6064(2) 0.43325(10) 0.0834(8) Uani 1 1 d . . . O4 O 0.4882(3) 0.5248(2) 0.38209(11) 0.0899(8) Uani 1 1 d . . . N1 N 0.0622(3) 0.5754(2) 0.61629(11) 0.0654(8) Uani 1 1 d D . . H1N H 0.1061 0.5636 0.5943 0.079 Uiso 1 1 d RD . . N2 N 0.0616(3) 0.3940(2) 0.61360(11) 0.0555(7) Uani 1 1 d D . . H2N H 0.0321 0.3229 0.6281 0.067 Uiso 1 1 d RD . . N3 N 0.1295(3) 0.4041(2) 0.56788(10) 0.0520(7) Uani 1 1 d . . . N4 N 0.4293(4) 0.1293(3) 0.41494(14) 0.0745(9) Uani 1 1 d . . . N5 N 0.4027(3) 0.5244(3) 0.41621(13) 0.0665(8) Uani 1 1 d . . . C1 C 0.0380(3) 0.6867(3) 0.62554(15) 0.0602(9) Uani 1 1 d . . . C2 C -0.0307(4) 0.7245(3) 0.66675(16) 0.0759(11) Uani 1 1 d D . . H2 H -0.0635 0.6756 0.6904 0.091 Uiso 1 1 calc RD . . C3 C -0.0519(4) 0.8346(4) 0.67353(19) 0.0926(14) Uani 1 1 d D . . H3 H -0.0991 0.8592 0.7016 0.111 Uiso 1 1 calc RD . . C4 C -0.0041(4) 0.9069(4) 0.6394(2) 0.0897(15) Uani 1 1 d D . . H4 H -0.0200 0.9806 0.6443 0.108 Uiso 1 1 calc RD . . C5 C 0.1197(5) 0.9452(3) 0.5605(2) 0.0925(15) Uani 1 1 d D . . H5 H 0.1083 1.0193 0.5655 0.111 Uiso 1 1 calc RD . . C6 C 0.1843(5) 0.9106(3) 0.5188(2) 0.0927(14) Uani 1 1 d D . . H6 H 0.2163 0.9609 0.4956 0.111 Uiso 1 1 calc RD . . C7 C 0.2037(4) 0.7989(3) 0.51018(16) 0.0785(11) Uani 1 1 d D . . H7 H 0.2480 0.7751 0.4814 0.094 Uiso 1 1 calc RD . . C8 C 0.1571(4) 0.7268(3) 0.54414(16) 0.0653(10) Uani 1 1 d D . . H8 H 0.1699 0.6532 0.5382 0.078 Uiso 1 1 calc RD . . C9 C 0.0896(3) 0.7593(3) 0.58829(16) 0.0595(9) Uani 1 1 d . . . C10 C 0.0692(4) 0.8728(3) 0.59652(18) 0.0715(11) Uani 1 1 d . . . C11 C 0.0230(3) 0.4826(3) 0.63970(13) 0.0541(8) Uani 1 1 d . . . C12 C 0.1838(3) 0.3125(3) 0.55245(12) 0.0474(8) Uani 1 1 d . . . C13 C 0.2603(3) 0.3195(3) 0.50500(12) 0.0450(7) Uani 1 1 d . . . C14 C 0.3080(3) 0.2245(3) 0.48320(13) 0.0519(8) Uani 1 1 d D . . H14 H 0.2891 0.1577 0.4978 0.062 Uiso 1 1 calc RD . . C15 C 0.3825(3) 0.2298(3) 0.44026(14) 0.0538(9) Uani 1 1 d . . . C16 C 0.4154(3) 0.3261(3) 0.41730(13) 0.0589(9) Uani 1 1 d D . . H16 H 0.4679 0.3284 0.3882 0.071 Uiso 1 1 calc RD . . C17 C 0.3662(3) 0.4191(3) 0.43991(13) 0.0502(8) Uani 1 1 d . . . C18 C 0.2868(3) 0.4180(2) 0.48207(13) 0.0497(8) Uani 1 1 d D . . H18 H 0.2513 0.4823 0.4952 0.060 Uiso 1 1 calc RD . . N6 N 0.6298(3) 0.6794(2) 0.83157(10) 0.0571(7) Uani 1 1 d D . . H6N H 0.7173 0.6893 0.8683 0.069 Uiso 1 1 d RD . . N7 N 0.5234(3) 0.5613(2) 0.75872(12) 0.0704(8) Uani 1 1 d . . . N8 N 0.3406(3) 0.6641(3) 0.80358(14) 0.0765(9) Uani 1 1 d . . . N9 N 0.5040(4) 0.7575(2) 0.74837(12) 0.0739(8) Uani 1 1 d . . . C19 C 0.4678(4) 0.6773(3) 0.84883(14) 0.0709(10) Uani 1 1 d D . . H19A H 0.4646 0.6178 0.8734 0.085 Uiso 1 1 calc RD . . H19B H 0.4516 0.7444 0.8669 0.085 Uiso 1 1 calc RD . . C20 C 0.3477(4) 0.7543(3) 0.76720(17) 0.0925(13) Uani 1 1 d D . . H20A H 0.3325 0.8219 0.7850 0.111 Uiso 1 1 calc RD . . H20B H 0.2596 0.7473 0.7370 0.111 Uiso 1 1 calc RD . . C21 C 0.6306(4) 0.7722(3) 0.79309(14) 0.0670(10) Uani 1 1 d D . . H21A H 0.6146 0.8402 0.8105 0.080 Uiso 1 1 calc RD . . H21B H 0.7353 0.7752 0.7816 0.080 Uiso 1 1 calc RD . . C22 C 0.3673(4) 0.5617(3) 0.77682(16) 0.0837(12) Uani 1 1 d D . . H22A H 0.3642 0.5017 0.8011 0.100 Uiso 1 1 calc RD . . H22B H 0.2800 0.5513 0.7467 0.100 Uiso 1 1 calc RD . . C23 C 0.6507(4) 0.5749(3) 0.80352(14) 0.0670(10) Uani 1 1 d D . . H23A H 0.7554 0.5749 0.7920 0.080 Uiso 1 1 calc RD . . H23B H 0.6493 0.5147 0.8278 0.080 Uiso 1 1 calc RD . . C24 C 0.5269(4) 0.6539(3) 0.72297(15) 0.0893(12) Uani 1 1 d D . . H24A H 0.6308 0.6547 0.7109 0.107 Uiso 1 1 calc RD . . H24B H 0.4416 0.6449 0.6921 0.107 Uiso 1 1 calc RD . . O6 O 0.0143(3) 0.6977(2) 0.82326(15) 0.1479(15) Uani 1 1 d D . . H1O H 0.0480 0.6773 0.8589 0.222 Uiso 1 1 d RD . . H2O H 0.1263 0.6882 0.8233 0.222 Uiso 1 1 d RD . . 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 0.0835(6) 0.0974(7) 0.0629(7) -0.0037(6) 0.0307(5) -0.0047(5) O1 0.0793(13) 0.0479(14) 0.0496(15) 0.0045(11) 0.0038(11) 0.0022(11) O2 0.139(2) 0.0618(17) 0.107(2) -0.0096(17) 0.0440(18) 0.0127(16) O3 0.125(2) 0.100(2) 0.067(2) -0.0149(17) 0.0369(18) 0.0176(15) O5 0.1066(19) 0.0582(17) 0.087(2) 0.0099(15) 0.0229(16) -0.0040(13) O4 0.0941(17) 0.100(2) 0.083(2) 0.0136(17) 0.0348(16) -0.0188(14) N1 0.0690(17) 0.061(2) 0.071(2) -0.0041(17) 0.0239(15) 0.0069(14) N2 0.0634(16) 0.0516(18) 0.055(2) 0.0075(15) 0.0193(15) -0.0011(13) N3 0.0576(16) 0.0520(18) 0.048(2) 0.0035(14) 0.0138(14) -0.0014(12) N4 0.081(2) 0.074(2) 0.067(3) -0.011(2) 0.0094(18) 0.0090(18) N5 0.0647(18) 0.077(2) 0.054(2) 0.007(2) 0.0009(15) -0.0104(18) C1 0.0480(18) 0.060(2) 0.068(3) -0.017(2) -0.0010(18) 0.0058(17) C2 0.069(2) 0.078(3) 0.079(3) -0.023(2) 0.010(2) 0.010(2) C3 0.076(3) 0.101(4) 0.097(4) -0.038(3) 0.004(2) 0.013(2) C4 0.070(3) 0.075(3) 0.112(4) -0.044(3) -0.017(3) 0.019(2) C5 0.090(3) 0.052(3) 0.121(5) -0.007(3) -0.022(3) 0.001(2) C6 0.095(3) 0.062(3) 0.110(4) 0.024(3) -0.011(3) -0.006(2) C7 0.084(2) 0.065(3) 0.085(3) 0.016(2) 0.010(2) -0.003(2) C8 0.064(2) 0.053(2) 0.076(3) 0.003(2) 0.006(2) 0.0017(17) C9 0.0489(18) 0.053(2) 0.070(3) -0.008(2) -0.0070(19) 0.0019(16) C10 0.056(2) 0.055(3) 0.093(4) -0.016(3) -0.014(2) 0.0040(18) C11 0.0425(16) 0.069(2) 0.050(2) 0.002(2) 0.0053(15) -0.0037(16) C12 0.0517(18) 0.046(2) 0.041(2) -0.0012(18) -0.0002(15) -0.0030(16) C13 0.0477(17) 0.052(2) 0.034(2) -0.0017(18) 0.0026(15) -0.0029(15) C14 0.0624(19) 0.054(2) 0.038(2) 0.0013(18) 0.0051(17) -0.0006(16) C15 0.060(2) 0.053(2) 0.046(2) -0.0023(19) 0.0017(18) 0.0067(16) C16 0.0551(18) 0.078(3) 0.042(2) -0.002(2) 0.0021(16) -0.0013(18) C17 0.0530(18) 0.050(2) 0.043(2) 0.0054(18) -0.0037(17) -0.0056(16) C18 0.0570(18) 0.054(2) 0.037(2) 0.0010(17) 0.0047(16) -0.0014(15) N6 0.0626(16) 0.0636(18) 0.0424(18) -0.0009(15) 0.0019(13) -0.0067(13) N7 0.073(2) 0.080(2) 0.057(2) -0.0171(17) 0.0092(17) -0.0057(15) N8 0.0497(16) 0.094(2) 0.088(3) 0.004(2) 0.0178(17) 0.0004(16) N9 0.079(2) 0.086(2) 0.054(2) 0.0161(18) 0.0052(17) 0.0023(17) C19 0.084(2) 0.074(2) 0.064(3) -0.005(2) 0.038(2) -0.0031(19) C20 0.072(3) 0.100(3) 0.098(4) 0.016(3) -0.003(2) 0.019(2) C21 0.076(2) 0.063(2) 0.065(3) 0.008(2) 0.018(2) -0.0065(17) C22 0.072(2) 0.090(3) 0.082(3) -0.006(2) -0.005(2) -0.023(2) C23 0.063(2) 0.062(2) 0.077(3) -0.002(2) 0.015(2) 0.0078(16) C24 0.105(3) 0.115(4) 0.048(3) -0.009(3) 0.011(2) -0.002(2) O6 0.0720(16) 0.119(2) 0.269(4) -0.075(3) 0.073(2) -0.0151(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.659(3) . ? O1 C12 1.291(3) . ? O2 N4 1.226(4) . ? O3 N4 1.218(4) . ? O5 N5 1.222(3) . ? O4 N5 1.223(3) . ? N1 C11 1.360(4) . ? N1 C1 1.413(4) . ? N1 H1N 0.7407 . ? N2 C11 1.349(4) . ? N2 N3 1.396(3) . ? N2 H2N 1.0001 . ? N3 C12 1.304(3) . ? N4 C15 1.483(4) . ? N5 C17 1.488(4) . ? C1 C2 1.371(4) . ? C1 C9 1.430(4) . ? C2 C3 1.384(5) . ? C2 H2 0.9300 . ? C3 C4 1.358(5) . ? C3 H3 0.9300 . ? C4 C10 1.414(5) . ? C4 H4 0.9300 . ? C5 C6 1.350(5) . ? C5 C10 1.401(5) . ? C5 H5 0.9300 . ? C6 C7 1.409(5) . ? C6 H6 0.9300 . ? C7 C8 1.349(4) . ? C7 H7 0.9300 . ? C8 C9 1.409(4) . ? C8 H8 0.9300 . ? C9 C10 1.430(4) . ? C12 C13 1.474(4) . ? C13 C18 1.384(4) . ? C13 C14 1.387(4) . ? C14 C15 1.359(4) . ? C14 H14 0.9300 . ? C15 C16 1.375(4) . ? C16 C17 1.380(4) . ? C16 H16 0.9300 . ? C17 C18 1.365(4) . ? C18 H18 0.9300 . ? N6 C19 1.495(4) . ? N6 C23 1.501(4) . ? N6 C21 1.511(4) . ? N6 H6N 1.0900 . ? N7 C23 1.427(4) . ? N7 C22 1.458(4) . ? N7 C24 1.467(4) . ? N8 C19 1.433(4) . ? N8 C20 1.459(4) . ? N8 C22 1.473(4) . ? N9 C21 1.423(4) . ? N9 C24 1.462(4) . ? N9 C20 1.469(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? O6 H1O 0.9400 . ? O6 H2O 0.9404 . ? 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 C11 N1 C1 133.7(3) . . ? C11 N1 H1N 111.2 . . ? C1 N1 H1N 115.1 . . ? C11 N2 N3 120.8(3) . . ? C11 N2 H2N 115.3 . . ? N3 N2 H2N 123.8 . . ? C12 N3 N2 113.1(3) . . ? O3 N4 O2 123.9(4) . . ? O3 N4 C15 119.0(4) . . ? O2 N4 C15 117.1(4) . . ? O5 N5 O4 123.7(3) . . ? O5 N5 C17 117.3(3) . . ? O4 N5 C17 118.9(3) . . ? C2 C1 N1 123.4(4) . . ? C2 C1 C9 121.3(3) . . ? N1 C1 C9 115.3(3) . . ? C1 C2 C3 120.7(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C10 121.6(4) . . ? C3 C4 H4 119.2 . . ? C10 C4 H4 119.2 . . ? C6 C5 C10 122.0(4) . . ? C6 C5 H5 119.0 . . ? C10 C5 H5 119.0 . . ? C5 C6 C7 120.4(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 119.2(4) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 122.3(3) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? C8 C9 C1 124.7(3) . . ? C8 C9 C10 118.1(4) . . ? C1 C9 C10 117.1(4) . . ? C5 C10 C4 123.1(4) . . ? C5 C10 C9 117.9(4) . . ? C4 C10 C9 119.0(4) . . ? N2 C11 N1 111.4(3) . . ? N2 C11 S1 120.7(3) . . ? N1 C11 S1 127.9(3) . . ? O1 C12 N3 125.4(3) . . ? O1 C12 C13 119.4(3) . . ? N3 C12 C13 115.1(3) . . ? C18 C13 C14 119.3(3) . . ? C18 C13 C12 121.9(3) . . ? C14 C13 C12 118.8(3) . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 122.9(3) . . ? C14 C15 N4 120.6(3) . . ? C16 C15 N4 116.5(4) . . ? C15 C16 C17 116.1(3) . . ? C15 C16 H16 121.9 . . ? C17 C16 H16 121.9 . . ? C18 C17 C16 123.2(3) . . ? C18 C17 N5 119.7(3) . . ? C16 C17 N5 117.1(3) . . ? C17 C18 C13 118.9(3) . . ? C17 C18 H18 120.6 . . ? C13 C18 H18 120.6 . . ? C19 N6 C23 108.4(2) . . ? C19 N6 C21 108.5(2) . . ? C23 N6 C21 108.8(3) . . ? C19 N6 H6N 104.2 . . ? C23 N6 H6N 113.1 . . ? C21 N6 H6N 113.5 . . ? C23 N7 C22 108.7(3) . . ? C23 N7 C24 108.5(3) . . ? C22 N7 C24 108.4(3) . . ? C19 N8 C20 108.8(3) . . ? C19 N8 C22 108.8(3) . . ? C20 N8 C22 109.2(3) . . ? C21 N9 C24 109.4(3) . . ? C21 N9 C20 108.2(3) . . ? C24 N9 C20 108.5(3) . . ? N8 C19 N6 109.8(3) . . ? N8 C19 H19A 109.7 . . ? N6 C19 H19A 109.7 . . ? N8 C19 H19B 109.7 . . ? N6 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? N8 C20 N9 111.8(3) . . ? N8 C20 H20A 109.3 . . ? N9 C20 H20A 109.3 . . ? N8 C20 H20B 109.3 . . ? N9 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? N9 C21 N6 109.9(2) . . ? N9 C21 H21A 109.7 . . ? N6 C21 H21A 109.7 . . ? N9 C21 H21B 109.7 . . ? N6 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? N7 C22 N8 111.6(3) . . ? N7 C22 H22A 109.3 . . ? N8 C22 H22A 109.3 . . ? N7 C22 H22B 109.3 . . ? N8 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? N7 C23 N6 110.6(2) . . ? N7 C23 H23A 109.5 . . ? N6 C23 H23A 109.5 . . ? N7 C23 H23B 109.5 . . ? N6 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? N9 C24 N7 112.5(3) . . ? N9 C24 H24A 109.1 . . ? N7 C24 H24A 109.1 . . ? N9 C24 H24B 109.1 . . ? N7 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? H1O O6 H2O 80.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N2 N3 C12 169.5(2) . . . . ? C11 N1 C1 C2 3.9(5) . . . . ? C11 N1 C1 C9 -175.7(3) . . . . ? N1 C1 C2 C3 -179.6(3) . . . . ? C9 C1 C2 C3 -0.1(5) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C3 C4 C10 -0.5(6) . . . . ? C10 C5 C6 C7 -0.2(6) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 C1 180.0(3) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C2 C1 C9 C8 -178.2(3) . . . . ? N1 C1 C9 C8 1.3(4) . . . . ? C2 C1 C9 C10 1.2(4) . . . . ? N1 C1 C9 C10 -179.3(2) . . . . ? C6 C5 C10 C4 -177.7(4) . . . . ? C6 C5 C10 C9 0.7(5) . . . . ? C3 C4 C10 C5 179.9(3) . . . . ? C3 C4 C10 C9 1.6(5) . . . . ? C8 C9 C10 C5 -0.9(4) . . . . ? C1 C9 C10 C5 179.7(3) . . . . ? C8 C9 C10 C4 177.6(3) . . . . ? C1 C9 C10 C4 -1.8(4) . . . . ? N3 N2 C11 N1 -1.3(3) . . . . ? N3 N2 C11 S1 178.36(18) . . . . ? C1 N1 C11 N2 175.2(3) . . . . ? C1 N1 C11 S1 -4.5(5) . . . . ? N2 N3 C12 O1 -0.9(4) . . . . ? N2 N3 C12 C13 -178.6(2) . . . . ? O1 C12 C13 C18 -171.6(2) . . . . ? N3 C12 C13 C18 6.3(4) . . . . ? O1 C12 C13 C14 7.8(4) . . . . ? N3 C12 C13 C14 -174.3(2) . . . . ? C18 C13 C14 C15 1.1(4) . . . . ? C12 C13 C14 C15 -178.3(2) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C13 C14 C15 N4 -177.7(2) . . . . ? O3 N4 C15 C14 177.4(3) . . . . ? O2 N4 C15 C14 -3.8(4) . . . . ? O3 N4 C15 C16 -1.3(4) . . . . ? O2 N4 C15 C16 177.6(3) . . . . ? C14 C15 C16 C17 -0.9(4) . . . . ? N4 C15 C16 C17 177.7(2) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? C15 C16 C17 N5 179.1(2) . . . . ? O5 N5 C17 C18 -5.6(4) . . . . ? O4 N5 C17 C18 172.6(3) . . . . ? O5 N5 C17 C16 174.2(3) . . . . ? O4 N5 C17 C16 -7.5(4) . . . . ? C16 C17 C18 C13 2.9(4) . . . . ? N5 C17 C18 C13 -177.2(2) . . . . ? C14 C13 C18 C17 -2.9(4) . . . . ? C12 C13 C18 C17 176.5(2) . . . . ? C20 N8 C19 N6 -59.4(4) . . . . ? C22 N8 C19 N6 59.5(4) . . . . ? C23 N6 C19 N8 -59.1(3) . . . . ? C21 N6 C19 N8 58.9(3) . . . . ? C19 N8 C20 N9 60.9(4) . . . . ? C22 N8 C20 N9 -57.7(4) . . . . ? C21 N9 C20 N8 -61.3(4) . . . . ? C24 N9 C20 N8 57.3(4) . . . . ? C24 N9 C21 N6 -58.2(4) . . . . ? C20 N9 C21 N6 59.8(3) . . . . ? C19 N6 C21 N9 -59.7(3) . . . . ? C23 N6 C21 N9 58.0(3) . . . . ? C23 N7 C22 N8 59.9(4) . . . . ? C24 N7 C22 N8 -57.8(4) . . . . ? C19 N8 C22 N7 -60.5(4) . . . . ? C20 N8 C22 N7 58.2(4) . . . . ? C22 N7 C23 N6 -59.1(4) . . . . ? C24 N7 C23 N6 58.6(4) . . . . ? C19 N6 C23 N7 59.1(4) . . . . ? C21 N6 C23 N7 -58.7(3) . . . . ? C21 N9 C24 N7 59.9(4) . . . . ? C20 N9 C24 N7 -57.9(4) . . . . ? C23 N7 C24 N9 -59.5(4) . . . . ? C22 N7 C24 N9 58.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.227 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.043 data_Complex3 _database_code_depnum_ccdc_archive 'CCDC 844827' #TrackingRef '- all cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N6 O5 S' _chemical_formula_weight 512.59 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' 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' H H 0.0000 0.0000 '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 12.6988(14) _cell_length_b 15.4250(18) _cell_length_c 14.7893(18) _cell_angle_alpha 90.00 _cell_angle_beta 118.108(8) _cell_angle_gamma 90.00 _cell_volume 2555.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2464 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 19.08 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.949 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 31806 _diffrn_reflns_av_R_equivalents 0.1417 _diffrn_reflns_av_sigmaI/netI 0.2236 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.45 _reflns_number_total 6402 _reflns_number_gt 6385 _reflns_threshold_expression >2\s(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^ > 2\s(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^)+(0.0589P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5774 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2544 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1580 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.005 _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 0.51978(10) 0.22901(8) 0.53305(10) 0.0781(4) Uani 1 1 d . . . O1 O 0.3844(2) 0.53001(15) 0.39136(18) 0.0528(7) Uani 1 1 d . . . O5 O 0.1796(3) 0.8131(2) 0.3037(3) 0.0981(12) Uani 1 1 d . . . O4 O -0.0031(3) 0.8230(2) 0.2717(2) 0.0900(11) Uani 1 1 d . . . O2 O -0.1025(3) 0.4618(3) 0.3921(3) 0.0950(12) Uani 1 1 d . . . O3 O -0.1891(3) 0.5871(3) 0.3517(3) 0.1128(14) Uani 1 1 d . . . N5 N 0.0899(4) 0.7818(3) 0.2999(3) 0.0716(11) Uani 1 1 d . . . N4 N -0.1067(4) 0.5380(3) 0.3682(3) 0.0793(13) Uani 1 1 d . . . N3 N 0.2965(3) 0.4246(2) 0.4459(2) 0.0491(9) Uani 1 1 d . . . N2 N 0.4007(3) 0.3750(2) 0.4765(2) 0.0543(9) Uani 1 1 d D . . H2N H 0.4674 0.4000 0.4913 0.065 Uiso 1 1 calc RD . . N1 N 0.2816(3) 0.2594(2) 0.4438(3) 0.0640(10) Uani 1 1 d D . . H1N H 0.2285 0.2997 0.4240 0.077 Uiso 1 1 calc RD . . C1 C 0.2358(4) 0.1749(3) 0.4308(3) 0.0574(11) Uani 1 1 d . . . C2 C 0.2888(4) 0.1043(3) 0.4152(3) 0.0719(13) Uani 1 1 d D . . H2 H 0.3618 0.1102 0.4155 0.086 Uiso 1 1 calc RD . . C3 C 0.2339(5) 0.0217(3) 0.3986(3) 0.0818(15) Uani 1 1 d D . . H3 H 0.2720 -0.0267 0.3900 0.098 Uiso 1 1 calc RD . . C4 C 0.1256(5) 0.0130(3) 0.3953(3) 0.0829(16) Uani 1 1 d D . . H4 H 0.0895 -0.0412 0.3829 0.100 Uiso 1 1 calc RD . . C10 C 0.0680(5) 0.0839(3) 0.4101(3) 0.0668(13) Uani 1 1 d . . . C9 C 0.1236(4) 0.1668(3) 0.4303(3) 0.0577(12) Uani 1 1 d . . . C8 C 0.0642(4) 0.2362(3) 0.4478(3) 0.0653(13) Uani 1 1 d D . . H8 H 0.1002 0.2905 0.4628 0.078 Uiso 1 1 calc RD . . C7 C -0.0448(5) 0.2263(4) 0.4433(3) 0.0834(15) Uani 1 1 d D . . H7 H -0.0821 0.2736 0.4551 0.100 Uiso 1 1 calc RD . . C6 C -0.1008(5) 0.1449(4) 0.4210(4) 0.0926(18) Uani 1 1 d D . . H6 H -0.1759 0.1387 0.4166 0.111 Uiso 1 1 calc RD . . C5 C -0.0460(5) 0.0758(4) 0.4060(4) 0.0886(16) Uani 1 1 d D . . H5 H -0.0832 0.0219 0.3927 0.106 Uiso 1 1 calc RD . . C11 C 0.3957(4) 0.2881(3) 0.4824(3) 0.0534(11) Uani 1 1 d . . . C12 C 0.3000(4) 0.4995(3) 0.4066(3) 0.0463(10) Uani 1 1 d . . . C13 C 0.1929(3) 0.5553(3) 0.3802(3) 0.0458(10) Uani 1 1 d . . . C18 C 0.1917(3) 0.6409(3) 0.3525(3) 0.0475(10) Uani 1 1 d D . . H18 H 0.2573 0.6648 0.3497 0.057 Uiso 1 1 calc RD . . C17 C 0.0912(4) 0.6905(3) 0.3289(3) 0.0496(11) Uani 1 1 d . . . C16 C -0.0081(4) 0.6585(3) 0.3322(3) 0.0590(12) Uani 1 1 d D . . H16 H -0.0750 0.6926 0.3159 0.071 Uiso 1 1 calc RD . . C15 C -0.0027(4) 0.5736(3) 0.3607(3) 0.0546(11) Uani 1 1 d . . . C14 C 0.0935(4) 0.5213(3) 0.3840(3) 0.0547(11) Uani 1 1 d D . . H14 H 0.0927 0.4638 0.4023 0.066 Uiso 1 1 calc RD . . N6 N 0.4639(4) 0.4383(3) 0.2753(3) 0.0725(11) Uani 1 1 d D . . C21 C 0.5779(5) 0.3981(4) 0.3515(4) 0.128(2) Uani 1 1 d D . . H21A H 0.6304 0.4441 0.3933 0.153 Uiso 1 1 calc RD . . H21B H 0.5608 0.3617 0.3965 0.153 Uiso 1 1 calc RD . . C22 C 0.6438(4) 0.3454(4) 0.3115(5) 0.146(3) Uani 1 1 d D . . H22B H 0.5956 0.2969 0.2740 0.219 Uiso 1 1 calc RD . . H22C H 0.7166 0.3248 0.3676 0.219 Uiso 1 1 calc RD . . H22A H 0.6620 0.3802 0.2669 0.219 Uiso 1 1 calc RD . . C20 C 0.4770(6) 0.5882(4) 0.2204(5) 0.146(3) Uani 1 1 d D . . H20B H 0.4095 0.6029 0.2300 0.220 Uiso 1 1 calc RD . . H20C H 0.4658 0.6113 0.1561 0.220 Uiso 1 1 calc RD . . H20A H 0.5481 0.6125 0.2752 0.220 Uiso 1 1 calc RD . . C24 C 0.2787(6) 0.3510(4) 0.2057(4) 0.143(3) Uani 1 1 d D . . H24B H 0.2662 0.3806 0.2570 0.214 Uiso 1 1 calc RD . . H24C H 0.2766 0.2895 0.2148 0.214 Uiso 1 1 calc RD . . H24A H 0.2169 0.3669 0.1388 0.214 Uiso 1 1 calc RD . . C23 C 0.3826(6) 0.3728(7) 0.2145(6) 0.258(6) Uani 1 1 d D . . H23A H 0.3672 0.3852 0.1450 0.309 Uiso 1 1 calc RD . . H23B H 0.4289 0.3197 0.2339 0.309 Uiso 1 1 calc RD . . C19 C 0.4875(11) 0.5042(6) 0.2202(8) 0.278(7) Uani 1 1 d D . . H19A H 0.5699 0.4947 0.2360 0.333 Uiso 1 1 calc RD . . H19B H 0.4401 0.4879 0.1488 0.333 Uiso 1 1 calc RD . . H6N H 0.441(4) 0.465(3) 0.328(3) 0.122(17) Uiso 1 1 d 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 0.0639(9) 0.0611(8) 0.0938(10) 0.0124(7) 0.0244(8) 0.0033(7) O1 0.0507(18) 0.0519(18) 0.0642(18) -0.0011(14) 0.0339(16) -0.0071(14) O5 0.085(3) 0.064(2) 0.146(3) 0.015(2) 0.055(3) -0.003(2) O4 0.085(3) 0.070(2) 0.109(3) -0.0028(19) 0.041(2) 0.019(2) O2 0.080(3) 0.111(3) 0.114(3) -0.006(3) 0.061(2) -0.025(2) O3 0.069(3) 0.146(4) 0.146(3) 0.009(3) 0.070(3) 0.009(2) N5 0.070(3) 0.063(3) 0.075(3) -0.009(2) 0.029(3) 0.002(3) N4 0.063(3) 0.105(4) 0.081(3) -0.008(3) 0.043(3) -0.010(3) N3 0.044(2) 0.043(2) 0.058(2) -0.0016(18) 0.0220(19) -0.0024(18) N2 0.048(2) 0.049(2) 0.068(2) 0.0006(19) 0.028(2) -0.009(2) N1 0.056(3) 0.044(2) 0.082(3) 0.0007(19) 0.024(2) -0.007(2) C1 0.063(3) 0.046(3) 0.058(3) -0.001(2) 0.024(3) -0.015(3) C2 0.085(4) 0.056(3) 0.073(3) -0.004(3) 0.035(3) -0.007(3) C3 0.115(5) 0.053(4) 0.073(4) -0.010(3) 0.041(3) -0.013(3) C4 0.110(5) 0.059(4) 0.071(4) -0.003(3) 0.035(4) -0.027(3) C10 0.077(4) 0.064(4) 0.047(3) 0.008(3) 0.020(3) -0.021(3) C9 0.073(4) 0.057(3) 0.035(3) -0.001(2) 0.018(3) -0.013(3) C8 0.059(3) 0.081(4) 0.052(3) -0.002(2) 0.023(3) -0.021(3) C7 0.082(4) 0.099(4) 0.067(4) 0.002(3) 0.034(3) -0.008(3) C6 0.077(4) 0.122(6) 0.077(4) 0.008(4) 0.034(3) -0.028(4) C5 0.092(5) 0.091(5) 0.068(4) 0.008(3) 0.026(3) -0.040(4) C11 0.055(3) 0.052(3) 0.048(3) 0.000(2) 0.020(2) -0.008(3) C12 0.045(3) 0.046(3) 0.046(3) -0.009(2) 0.020(2) -0.006(2) C13 0.043(3) 0.056(3) 0.038(2) -0.006(2) 0.019(2) -0.008(2) C18 0.045(3) 0.053(3) 0.042(3) -0.006(2) 0.019(2) -0.003(2) C17 0.057(3) 0.046(3) 0.041(3) -0.008(2) 0.020(2) -0.004(3) C16 0.051(3) 0.076(4) 0.051(3) -0.013(3) 0.024(2) 0.001(3) C15 0.048(3) 0.072(4) 0.051(3) -0.010(2) 0.030(2) -0.014(3) C14 0.052(3) 0.060(3) 0.056(3) -0.005(2) 0.029(3) -0.005(3) N6 0.074(3) 0.080(3) 0.082(3) -0.001(3) 0.052(3) 0.004(2) C21 0.089(4) 0.186(7) 0.101(5) -0.028(4) 0.040(4) 0.039(4) C22 0.079(4) 0.185(7) 0.168(6) -0.055(5) 0.054(4) 0.020(4) C20 0.188(7) 0.125(6) 0.187(7) 0.037(5) 0.138(6) -0.005(5) C24 0.171(7) 0.175(7) 0.097(4) -0.057(4) 0.077(5) -0.084(5) C23 0.088(5) 0.449(15) 0.255(10) -0.293(11) 0.097(6) -0.117(7) C19 0.55(2) 0.146(8) 0.379(14) 0.100(9) 0.419(15) 0.119(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.662(4) . ? O1 C12 1.284(4) . ? O5 N5 1.213(4) . ? O4 N5 1.228(4) . ? O2 N4 1.222(4) . ? O3 N4 1.220(4) . ? N5 C17 1.469(5) . ? N4 C15 1.482(5) . ? N3 C12 1.304(4) . ? N3 N2 1.406(4) . ? N2 C11 1.345(4) . ? N2 H2N 0.8600 . ? N1 C11 1.358(4) . ? N1 C1 1.403(5) . ? N1 H1N 0.8600 . ? C1 C2 1.355(5) . ? C1 C9 1.427(5) . ? C2 C3 1.418(5) . ? C2 H2 0.9300 . ? C3 C4 1.359(6) . ? C3 H3 0.9300 . ? C4 C10 1.388(6) . ? C4 H4 0.9300 . ? C10 C5 1.426(6) . ? C10 C9 1.423(5) . ? C9 C8 1.402(5) . ? C8 C7 1.363(5) . ? C8 H8 0.9300 . ? C7 C6 1.403(6) . ? C7 H7 0.9300 . ? C6 C5 1.348(6) . ? C6 H6 0.9300 . ? C5 H5 0.9300 . ? C12 C13 1.498(5) . ? C13 C18 1.379(5) . ? C13 C14 1.392(4) . ? C18 C17 1.384(5) . ? C18 H18 0.9300 . ? C17 C16 1.376(5) . ? C16 C15 1.368(5) . ? C16 H16 0.9300 . ? C15 C14 1.365(5) . ? C14 H14 0.9300 . ? N6 C19 1.420(7) . ? N6 C23 1.421(7) . ? N6 C21 1.488(5) . ? N6 H6N 1.03(2) . ? C21 C22 1.475(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22 H22A 0.9600 . ? C20 C19 1.303(8) . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C20 H20A 0.9600 . ? C24 C23 1.308(7) . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C24 H24A 0.9600 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 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 O5 N5 O4 122.7(4) . . ? O5 N5 C17 119.1(4) . . ? O4 N5 C17 118.2(4) . . ? O3 N4 O2 124.9(4) . . ? O3 N4 C15 117.8(5) . . ? O2 N4 C15 117.4(4) . . ? C12 N3 N2 113.6(3) . . ? C11 N2 N3 119.8(3) . . ? C11 N2 H2N 120.1 . . ? N3 N2 H2N 120.1 . . ? C11 N1 C1 130.7(4) . . ? C11 N1 H1N 114.7 . . ? C1 N1 H1N 114.6 . . ? C2 C1 N1 124.3(4) . . ? C2 C1 C9 120.2(4) . . ? N1 C1 C9 115.5(4) . . ? C1 C2 C3 120.6(5) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C10 121.1(5) . . ? C3 C4 H4 119.5 . . ? C10 C4 H4 119.5 . . ? C4 C10 C5 121.6(5) . . ? C4 C10 C9 119.6(5) . . ? C5 C10 C9 118.8(5) . . ? C8 C9 C10 117.9(4) . . ? C8 C9 C1 123.7(4) . . ? C10 C9 C1 118.4(4) . . ? C7 C8 C9 121.9(4) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C8 C7 C6 120.1(5) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C5 C6 C7 120.2(5) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C5 C10 121.1(5) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? N2 C11 N1 111.8(4) . . ? N2 C11 S1 120.8(3) . . ? N1 C11 S1 127.4(3) . . ? O1 C12 N3 127.6(4) . . ? O1 C12 C13 118.3(4) . . ? N3 C12 C13 114.1(4) . . ? C18 C13 C14 119.3(4) . . ? C18 C13 C12 120.6(4) . . ? C14 C13 C12 120.1(4) . . ? C13 C18 C17 118.9(4) . . ? C13 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C16 C17 C18 122.9(4) . . ? C16 C17 N5 118.0(4) . . ? C18 C17 N5 119.1(4) . . ? C15 C16 C17 116.2(4) . . ? C15 C16 H16 121.9 . . ? C17 C16 H16 121.9 . . ? C14 C15 C16 123.5(4) . . ? C14 C15 N4 119.0(4) . . ? C16 C15 N4 117.5(4) . . ? C15 C14 C13 119.2(4) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C19 N6 C23 115.6(7) . . ? C19 N6 C21 109.9(6) . . ? C23 N6 C21 109.9(6) . . ? C19 N6 H6N 111(2) . . ? C23 N6 H6N 112(2) . . ? C21 N6 H6N 97(2) . . ? C22 C21 N6 117.3(4) . . ? C22 C21 H21A 108.0 . . ? N6 C21 H21A 108.0 . . ? C22 C21 H21B 108.0 . . ? N6 C21 H21B 108.0 . . ? H21A C21 H21B 107.2 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C22 H22A 109.5 . . ? H22B C22 H22A 109.5 . . ? H22C C22 H22A 109.5 . . ? C19 C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C20 H20A 109.4 . . ? H20B C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C24 H24A 109.5 . . ? H24B C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? C24 C23 N6 130.1(5) . . ? C24 C23 H23A 104.7 . . ? N6 C23 H23A 104.8 . . ? C24 C23 H23B 104.7 . . ? N6 C23 H23B 104.7 . . ? H23A C23 H23B 105.8 . . ? C20 C19 N6 131.4(6) . . ? C20 C19 H19A 104.4 . . ? N6 C19 H19A 104.4 . . ? C20 C19 H19B 104.4 . . ? N6 C19 H19B 104.4 . . ? H19A C19 H19B 105.6 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.228 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.041