# 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_1 _database_code_depnum_ccdc_archive 'CCDC 905091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 N5 O7 Zn' _chemical_formula_weight 566.84 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8798(6) _cell_length_b 9.2592(6) _cell_length_c 15.0913(10) _cell_angle_alpha 104.7570(10) _cell_angle_beta 99.5260(10) _cell_angle_gamma 90.5160(10) _cell_volume 1181.63(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.637 _cell_measurement_theta_max 0.688 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 1.098 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.637 _exptl_absorpt_correction_T_max 0.688 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6299 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4164 _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^)+(0.0557P)^2^+0.5170P] 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 4144 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.49320(3) 0.22647(3) 0.149737(19) 0.03132(12) Uani 1 1 d . . . O1W O 1.0370(2) 0.2312(2) 0.31042(14) 0.0486(5) Uani 1 1 d . . . H1WA H 1.0335 0.2281 0.2533 0.058 Uiso 1 1 d R . . H2WB H 1.0627 0.3206 0.3419 0.058 Uiso 1 1 d R . . O1 O 0.3523(2) 0.3265(3) 0.07479(15) 0.0537(6) Uani 1 1 d . . . N1 N 0.5743(2) 0.3720(2) 0.27950(15) 0.0314(5) Uani 1 1 d . . . C1 C 0.5054(3) 0.4961(3) 0.31711(19) 0.0359(6) Uani 1 1 d . . . H1A H 0.4214 0.5251 0.2813 0.043 Uiso 1 1 calc R . . N2 N 0.8737(2) 0.3534(2) 0.47156(14) 0.0311(5) Uani 1 1 d . . . H2B H 0.9381 0.3079 0.4389 0.037 Uiso 1 1 calc R . . C2 C 0.6931(3) 0.3323(3) 0.33364(18) 0.0314(5) Uani 1 1 d . . . H2A H 0.7414 0.2463 0.3087 0.038 Uiso 1 1 calc R . . O2 O 0.6490(2) 0.1618(2) 0.07199(13) 0.0429(5) Uani 1 1 d . . . N3 N 1.0900(2) 0.1781(2) 0.52406(14) 0.0276(4) Uani 1 1 d . . . O3 O 0.7727(2) 0.0715(2) 0.18492(13) 0.0452(5) Uani 1 1 d . . . C3 C 0.5545(3) 0.5815(3) 0.4066(2) 0.0390(6) Uani 1 1 d . . . H3A H 0.5046 0.6671 0.4299 0.047 Uiso 1 1 calc R . . N4 N 1.2379(2) 0.0322(2) 0.39055(15) 0.0343(5) Uani 1 1 d . . . H4B H 1.1683 0.0953 0.3864 0.041 Uiso 1 1 calc R . . C4 C 0.6777(3) 0.5401(3) 0.46150(19) 0.0342(6) Uani 1 1 d . . . H4A H 0.7125 0.5971 0.5220 0.041 Uiso 1 1 calc R . . O4 O 0.2000(2) 0.3254(2) 0.17631(15) 0.0525(5) Uani 1 1 d . . . O5 O 0.8341(2) 0.4392(2) 0.62095(13) 0.0478(5) Uani 1 1 d . . . C5 C 0.7483(3) 0.4110(3) 0.42404(17) 0.0287(5) Uani 1 1 d . . . N5 N 1.4205(2) 0.0490(2) 0.19431(14) 0.0315(5) Uani 1 1 d . . . O6 O 1.3520(2) -0.1078(2) 0.48402(14) 0.0456(5) Uani 1 1 d . . . C6 C 0.9024(3) 0.3628(3) 0.56356(17) 0.0321(6) Uani 1 1 d . . . C7 C 1.0271(3) 0.2656(3) 0.59162(17) 0.0302(5) Uani 1 1 d . . . C8 C 1.0690(3) 0.2679(3) 0.68446(19) 0.0427(7) Uani 1 1 d . . . H8A H 1.0243 0.3320 0.7298 0.051 Uiso 1 1 calc R . . C9 C 1.1787(3) 0.1730(4) 0.7084(2) 0.0481(7) Uani 1 1 d . . . H9A H 1.2088 0.1718 0.7702 0.058 Uiso 1 1 calc R . . C10 C 1.2428(3) 0.0802(3) 0.63913(19) 0.0404(6) Uani 1 1 d . . . H10A H 1.3157 0.0142 0.6532 0.049 Uiso 1 1 calc R . . C11 C 1.1967(3) 0.0873(3) 0.54841(17) 0.0292(5) Uani 1 1 d . . . C12 C 1.2698(3) -0.0076(3) 0.47142(18) 0.0311(5) Uani 1 1 d . . . C13 C 1.3085(3) -0.0206(3) 0.31233(18) 0.0314(5) Uani 1 1 d . . . C14 C 1.3532(3) 0.0840(3) 0.26912(17) 0.0313(5) Uani 1 1 d . . . H14A H 1.3352 0.1839 0.2936 0.038 Uiso 1 1 calc R . . C15 C 1.3324(3) -0.1697(3) 0.27463(19) 0.0378(6) Uani 1 1 d . . . H15A H 1.3022 -0.2436 0.3007 0.045 Uiso 1 1 calc R . . C16 C 1.4025(3) -0.2056(3) 0.19705(19) 0.0406(6) Uani 1 1 d . . . H16A H 1.4207 -0.3047 0.1707 0.049 Uiso 1 1 calc R . . C17 C 1.4453(3) -0.0953(3) 0.15880(18) 0.0357(6) Uani 1 1 d . . . H17A H 1.4928 -0.1214 0.1069 0.043 Uiso 1 1 calc R . . C18 C 0.2259(3) 0.3557(3) 0.1059(2) 0.0393(6) Uani 1 1 d . . . C19 C 0.1102(3) 0.4314(3) 0.05036(18) 0.0351(6) Uani 1 1 d . . . C20 C 0.1383(3) 0.4673(3) -0.0292(2) 0.0413(7) Uani 1 1 d . . . H20A H 0.2312 0.4459 -0.0491 0.050 Uiso 1 1 calc R . . C21 C 0.0280(3) 0.5352(3) -0.07966(19) 0.0402(6) Uani 1 1 d . . . H21A H 0.0475 0.5583 -0.1333 0.048 Uiso 1 1 calc R . . C22 C 0.7604(3) 0.0953(3) 0.10732(18) 0.0331(6) Uani 1 1 d . . . C23 C 0.8833(3) 0.0458(3) 0.05021(17) 0.0289(5) Uani 1 1 d . . . C24 C 0.9877(3) -0.0541(3) 0.07604(17) 0.0330(6) Uani 1 1 d . . . H24A H 0.9793 -0.0903 0.1272 0.040 Uiso 1 1 calc R . . C25 C 1.1029(3) -0.0993(3) 0.02614(17) 0.0319(6) Uani 1 1 d . . . H25A H 1.1720 -0.1660 0.0437 0.038 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 0.02674(17) 0.0430(2) 0.03007(18) 0.01744(13) 0.00814(12) 0.01601(12) O1W 0.0412(11) 0.0656(14) 0.0449(12) 0.0213(10) 0.0120(9) 0.0189(10) O1 0.0368(11) 0.0743(15) 0.0617(14) 0.0396(12) 0.0058(10) 0.0253(10) N1 0.0272(11) 0.0326(11) 0.0381(12) 0.0145(9) 0.0073(9) 0.0102(9) C1 0.0311(14) 0.0334(14) 0.0468(16) 0.0161(12) 0.0074(12) 0.0124(11) N2 0.0253(11) 0.0364(12) 0.0317(11) 0.0083(9) 0.0061(9) 0.0097(9) C2 0.0271(13) 0.0317(13) 0.0374(14) 0.0105(11) 0.0081(11) 0.0117(10) O2 0.0317(10) 0.0632(13) 0.0410(11) 0.0201(9) 0.0153(8) 0.0233(9) N3 0.0239(10) 0.0297(11) 0.0297(11) 0.0099(9) 0.0032(8) 0.0002(8) O3 0.0438(11) 0.0630(13) 0.0348(11) 0.0162(9) 0.0176(9) 0.0234(9) C3 0.0372(15) 0.0275(13) 0.0549(18) 0.0110(12) 0.0144(13) 0.0142(11) N4 0.0338(12) 0.0377(12) 0.0391(12) 0.0188(10) 0.0137(10) 0.0152(9) C4 0.0364(14) 0.0275(13) 0.0387(14) 0.0059(11) 0.0104(11) 0.0045(10) O4 0.0487(12) 0.0658(14) 0.0491(13) 0.0294(11) 0.0021(10) 0.0200(10) O5 0.0492(12) 0.0562(13) 0.0374(11) 0.0062(9) 0.0142(9) 0.0202(10) C5 0.0232(12) 0.0287(12) 0.0376(14) 0.0123(11) 0.0089(10) 0.0054(9) N5 0.0261(11) 0.0403(12) 0.0307(11) 0.0137(9) 0.0044(9) 0.0099(9) O6 0.0496(12) 0.0411(11) 0.0521(12) 0.0208(9) 0.0109(10) 0.0195(9) C6 0.0278(13) 0.0338(13) 0.0328(14) 0.0055(11) 0.0050(11) 0.0015(10) C7 0.0260(12) 0.0335(13) 0.0310(13) 0.0090(11) 0.0034(10) 0.0000(10) C8 0.0433(16) 0.0555(18) 0.0296(14) 0.0100(13) 0.0088(12) 0.0072(13) C9 0.0500(18) 0.066(2) 0.0319(15) 0.0229(14) 0.0022(13) 0.0083(15) C10 0.0379(15) 0.0485(16) 0.0407(16) 0.0240(13) 0.0035(12) 0.0069(12) C11 0.0257(12) 0.0292(12) 0.0344(13) 0.0125(10) 0.0036(10) -0.0004(10) C12 0.0262(13) 0.0315(13) 0.0387(14) 0.0156(11) 0.0042(11) 0.0019(10) C13 0.0235(12) 0.0384(14) 0.0356(14) 0.0151(11) 0.0055(10) 0.0096(10) C14 0.0279(13) 0.0327(13) 0.0356(14) 0.0114(11) 0.0072(11) 0.0091(10) C15 0.0377(15) 0.0348(14) 0.0458(16) 0.0181(12) 0.0084(12) 0.0096(11) C16 0.0450(16) 0.0325(14) 0.0419(16) 0.0055(12) 0.0068(13) 0.0106(12) C17 0.0338(14) 0.0439(15) 0.0285(13) 0.0076(11) 0.0047(11) 0.0121(11) C18 0.0353(15) 0.0381(15) 0.0423(16) 0.0131(12) -0.0039(12) 0.0097(11) C19 0.0328(14) 0.0303(13) 0.0376(15) 0.0074(11) -0.0055(11) 0.0087(11) C20 0.0340(14) 0.0440(16) 0.0466(16) 0.0147(13) 0.0039(12) 0.0173(12) C21 0.0405(16) 0.0436(16) 0.0381(15) 0.0160(12) 0.0017(12) 0.0155(12) C22 0.0288(13) 0.0389(14) 0.0310(14) 0.0052(11) 0.0090(11) 0.0075(11) C23 0.0215(12) 0.0341(13) 0.0284(13) 0.0032(10) 0.0042(10) 0.0060(10) C24 0.0312(13) 0.0412(15) 0.0288(13) 0.0116(11) 0.0070(11) 0.0072(11) C25 0.0275(13) 0.0366(14) 0.0303(13) 0.0070(11) 0.0036(10) 0.0115(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9462(18) . ? Zn1 O2 1.9606(17) . ? Zn1 N5 2.063(2) 1_455 ? Zn1 N1 2.084(2) . ? O1 C18 1.292(3) . ? N1 C2 1.339(3) . ? N1 C1 1.345(3) . ? C1 C3 1.376(4) . ? N2 C6 1.349(3) . ? N2 C5 1.408(3) . ? C2 C5 1.378(4) . ? O2 C22 1.283(3) . ? N3 C7 1.335(3) . ? N3 C11 1.341(3) . ? O3 C22 1.234(3) . ? C3 C4 1.378(4) . ? N4 C12 1.350(3) . ? N4 C13 1.408(3) . ? C4 C5 1.389(3) . ? O4 C18 1.221(3) . ? O5 C6 1.220(3) . ? N5 C14 1.333(3) . ? N5 C17 1.342(3) . ? N5 Zn1 2.063(2) 1_655 ? O6 C12 1.219(3) . ? C6 C7 1.508(3) . ? C7 C8 1.383(4) . ? C8 C9 1.384(4) . ? C9 C10 1.380(4) . ? C10 C11 1.381(4) . ? C11 C12 1.511(4) . ? C13 C14 1.386(4) . ? C13 C15 1.385(4) . ? C15 C16 1.384(4) . ? C16 C17 1.373(4) . ? C18 C19 1.509(3) . ? C19 C20 1.383(4) . ? C19 C21 1.384(4) 2_565 ? C20 C21 1.394(4) . ? C21 C19 1.384(4) 2_565 ? C22 C23 1.504(3) . ? C23 C25 1.387(4) 2_755 ? C23 C24 1.395(3) . ? C24 C25 1.376(3) . ? C25 C23 1.387(4) 2_755 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O2 102.97(8) . . ? O1 Zn1 N5 121.56(9) . 1_455 ? O2 Zn1 N5 109.48(8) . 1_455 ? O1 Zn1 N1 110.07(9) . . ? O2 Zn1 N1 115.04(8) . . ? N5 Zn1 N1 98.37(8) 1_455 . ? C18 O1 Zn1 113.19(18) . . ? C2 N1 C1 117.1(2) . . ? C2 N1 Zn1 118.17(16) . . ? C1 N1 Zn1 124.36(17) . . ? N1 C1 C3 122.5(2) . . ? C6 N2 C5 126.1(2) . . ? N1 C2 C5 123.9(2) . . ? C22 O2 Zn1 115.75(16) . . ? C7 N3 C11 117.6(2) . . ? C1 C3 C4 120.0(2) . . ? C12 N4 C13 125.7(2) . . ? C3 C4 C5 118.1(2) . . ? C2 C5 C4 118.4(2) . . ? C2 C5 N2 116.7(2) . . ? C4 C5 N2 124.9(2) . . ? C14 N5 C17 118.1(2) . . ? C14 N5 Zn1 116.08(17) . 1_655 ? C17 N5 Zn1 125.60(18) . 1_655 ? O5 C6 N2 124.9(2) . . ? O5 C6 C7 121.0(2) . . ? N2 C6 C7 114.1(2) . . ? N3 C7 C8 123.1(2) . . ? N3 C7 C6 117.5(2) . . ? C8 C7 C6 119.4(2) . . ? C7 C8 C9 118.6(3) . . ? C10 C9 C8 119.0(3) . . ? C9 C10 C11 118.7(3) . . ? N3 C11 C10 123.1(2) . . ? N3 C11 C12 116.9(2) . . ? C10 C11 C12 120.1(2) . . ? O6 C12 N4 124.6(2) . . ? O6 C12 C11 121.7(2) . . ? N4 C12 C11 113.7(2) . . ? C14 C13 C15 118.2(2) . . ? C14 C13 N4 117.3(2) . . ? C15 C13 N4 124.4(2) . . ? N5 C14 C13 123.4(2) . . ? C16 C15 C13 118.2(2) . . ? C17 C16 C15 120.3(2) . . ? N5 C17 C16 121.8(2) . . ? O4 C18 O1 122.8(2) . . ? O4 C18 C19 121.2(3) . . ? O1 C18 C19 116.0(3) . . ? C20 C19 C21 119.3(2) . 2_565 ? C20 C19 C18 121.8(2) . . ? C21 C19 C18 118.9(3) 2_565 . ? C19 C20 C21 120.3(3) . . ? C19 C21 C20 120.4(3) 2_565 . ? O3 C22 O2 123.9(2) . . ? O3 C22 C23 118.8(2) . . ? O2 C22 C23 117.3(2) . . ? C25 C23 C24 119.4(2) 2_755 . ? C25 C23 C22 121.6(2) 2_755 . ? C24 C23 C22 119.0(2) . . ? C25 C24 C23 120.3(2) . . ? C24 C25 C23 120.4(2) . 2_755 ? _diffrn_measured_fraction_theta_max 0.995 data_2 _database_code_depnum_ccdc_archive 'CCDC 905092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Cd N5 O7' _chemical_formula_weight 613.86 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.064(3) _cell_length_b 9.558(3) _cell_length_c 13.644(4) _cell_angle_alpha 95.546(4) _cell_angle_beta 91.307(5) _cell_angle_gamma 90.209(5) _cell_volume 1176.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.648 _exptl_absorpt_correction_T_max 0.694 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6242 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4151 _reflns_number_gt 3716 _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^)+(0.0352P)^2^+0.0113P] 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 4125 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Cd1 Cd 0.88039(2) 0.071471(19) 0.117362(12) 0.02445(8) Uani 1 1 d . . . O1 O 0.7280(2) 0.1867(2) 0.02118(14) 0.0342(5) Uani 1 1 d . . . N1 N 0.9664(2) 0.1270(2) 0.28054(16) 0.0297(5) Uani 1 1 d . . . C1 C 0.9030(3) 0.2325(3) 0.33446(19) 0.0286(6) Uani 1 1 d . . . H1A H 0.8309 0.2837 0.3042 0.034 Uiso 1 1 calc R . . O1W O 0.8154(2) 0.5638(2) 0.30337(15) 0.0434(5) Uani 1 1 d . . . H1WA H 0.8091 0.5183 0.2467 0.052 Uiso 1 1 d R . . H1WB H 0.9008 0.6010 0.3096 0.052 Uiso 1 1 d R . . O2 O 0.7708(2) 0.3314(2) 0.15493(14) 0.0390(5) Uani 1 1 d . . . N2 N 0.8566(2) 0.3847(2) 0.47926(15) 0.0281(5) Uani 1 1 d . . . H2B H 0.8227 0.4450 0.4418 0.034 Uiso 1 1 calc R . . C2 C 1.0688(3) 0.0519(3) 0.3249(2) 0.0324(7) Uani 1 1 d . . . H2A H 1.1116 -0.0247 0.2892 0.039 Uiso 1 1 calc R . . O3 O 1.0876(2) 0.12949(19) 0.02452(14) 0.0330(5) Uani 1 1 d . . . N3 N 0.6637(2) 0.5935(2) 0.52697(15) 0.0257(5) Uani 1 1 d . . . C3 C 0.9375(3) 0.2711(3) 0.43311(18) 0.0258(6) Uani 1 1 d . . . O4 O 0.9643(2) -0.1512(2) 0.13364(15) 0.0412(5) Uani 1 1 d . . . N4 N 0.5784(2) 0.7612(3) 0.38333(16) 0.0320(5) Uani 1 1 d . . . H4B H 0.6454 0.6976 0.3771 0.038 Uiso 1 1 calc R . . C4 C 1.0473(3) 0.1961(3) 0.4778(2) 0.0331(7) Uani 1 1 d . . . H4A H 1.0761 0.2199 0.5431 0.040 Uiso 1 1 calc R . . N5 N 0.6576(3) -0.0217(2) 0.18353(16) 0.0319(5) Uani 1 1 d . . . C5 C 1.1123(3) 0.0855(3) 0.4225(2) 0.0372(7) Uani 1 1 d . . . H5A H 1.1855 0.0334 0.4508 0.045 Uiso 1 1 calc R . . C6 C 0.8275(3) 0.4080(3) 0.57591(19) 0.0282(6) Uani 1 1 d . . . C7 C 0.6683(4) 0.5457(3) 0.6963(2) 0.0416(8) Uani 1 1 d . . . H7A H 0.7062 0.4938 0.7452 0.050 Uiso 1 1 calc R . . C8 C 0.5099(3) 0.7241(3) 0.6437(2) 0.0408(8) Uani 1 1 d . . . H8A H 0.4401 0.7942 0.6566 0.049 Uiso 1 1 calc R . . O9 O 0.8831(2) 0.3429(2) 0.64072(14) 0.0424(5) Uani 1 1 d . . . C9 C 0.5622(3) 0.6930(3) 0.54917(19) 0.0278(6) Uani 1 1 d . . . O10 O 0.3981(2) 0.8551(2) 0.48308(15) 0.0468(6) Uani 1 1 d . . . C10 C 0.7153(3) 0.5217(3) 0.60075(18) 0.0274(6) Uani 1 1 d . . . C11 C 0.5637(4) 0.6488(4) 0.7180(2) 0.0491(9) Uani 1 1 d . . . H11A H 0.5302 0.6669 0.7819 0.059 Uiso 1 1 calc R . . C12 C 0.5040(3) 0.7771(3) 0.4685(2) 0.0304(6) Uani 1 1 d . . . C13 C 0.5519(3) 0.8436(3) 0.30386(19) 0.0273(6) Uani 1 1 d . . . C14 C 0.4102(3) 0.8722(3) 0.2694(2) 0.0339(7) Uani 1 1 d . . . H14A H 0.3274 0.8367 0.2977 0.041 Uiso 1 1 calc R . . C15 C 0.6708(3) -0.1026(3) 0.2581(2) 0.0316(6) Uani 1 1 d . . . H15A H 0.7652 -0.1236 0.2803 0.038 Uiso 1 1 calc R . . C16 C 0.5200(3) 0.0060(3) 0.1513(2) 0.0320(7) Uani 1 1 d . . . H16A H 0.5086 0.0620 0.0996 0.038 Uiso 1 1 calc R . . C17 C 0.3962(3) 0.9547(3) 0.1919(2) 0.0362(7) Uani 1 1 d . . . H17A H 0.3030 0.9755 0.1674 0.043 Uiso 1 1 calc R . . C18 C 1.0505(3) 0.2030(3) -0.0452(2) 0.0298(6) Uani 1 1 d . . . C19 C 0.9515(3) 0.4332(3) -0.0898(2) 0.0311(6) Uani 1 1 d . . . H19A H 0.9191 0.3885 -0.1501 0.037 Uiso 1 1 calc R . . C20 C 0.7078(3) 0.3017(3) 0.07273(19) 0.0280(6) Uani 1 1 d . . . C21 C 0.6014(3) 0.4056(3) 0.03484(18) 0.0262(6) Uani 1 1 d . . . C22 C 0.5967(4) 0.5422(3) 0.0766(2) 0.0436(8) Uani 1 1 d . . . H22A H 0.6612 0.5716 0.1286 0.052 Uiso 1 1 calc R . . C23 C 0.5038(4) 0.3630(3) -0.0419(2) 0.0427(8) Uani 1 1 d . . . H23A H 0.5052 0.2706 -0.0704 0.051 Uiso 1 1 calc R . . C24 C 1.0732(3) 0.4250(3) 0.0681(2) 0.0303(6) Uani 1 1 d . . . H24A H 1.1225 0.3746 0.1136 0.036 Uiso 1 1 calc R . . C27 C 1.0243(3) 0.3567(3) -0.02208(19) 0.0258(6) 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 Cd1 0.03249(13) 0.01780(12) 0.02314(12) 0.00149(7) 0.00291(8) 0.00945(8) O1 0.0426(12) 0.0240(11) 0.0363(11) 0.0042(8) 0.0007(9) 0.0140(9) N1 0.0324(13) 0.0280(13) 0.0284(12) 0.0005(10) 0.0023(10) 0.0083(10) C1 0.0307(15) 0.0289(16) 0.0258(14) 0.0003(11) -0.0012(11) 0.0096(12) O1W 0.0466(13) 0.0466(14) 0.0359(12) -0.0018(10) 0.0002(10) 0.0074(11) O2 0.0429(12) 0.0419(13) 0.0323(11) 0.0066(9) -0.0074(9) 0.0167(10) N2 0.0362(13) 0.0273(13) 0.0206(11) 0.0016(9) 0.0001(9) 0.0094(10) C2 0.0318(15) 0.0281(16) 0.0368(16) -0.0006(12) 0.0029(12) 0.0105(13) O3 0.0357(11) 0.0180(10) 0.0463(12) 0.0073(8) 0.0061(9) 0.0066(8) N3 0.0276(12) 0.0269(13) 0.0223(11) 0.0000(9) 0.0025(9) 0.0001(10) C3 0.0269(14) 0.0240(15) 0.0265(14) 0.0026(11) 0.0002(11) 0.0018(11) O4 0.0607(14) 0.0236(11) 0.0381(12) -0.0053(9) 0.0104(10) 0.0122(10) N4 0.0300(13) 0.0323(14) 0.0351(13) 0.0086(10) 0.0074(10) 0.0116(11) C4 0.0319(15) 0.0374(18) 0.0293(15) 0.0005(12) -0.0062(12) 0.0058(13) N5 0.0344(13) 0.0276(13) 0.0345(13) 0.0066(10) 0.0027(10) 0.0044(11) C5 0.0293(15) 0.0380(18) 0.0448(18) 0.0068(14) -0.0045(13) 0.0137(14) C6 0.0291(14) 0.0298(16) 0.0251(14) 0.0003(11) -0.0017(11) -0.0008(12) C7 0.056(2) 0.045(2) 0.0244(15) 0.0059(13) 0.0056(14) 0.0094(16) C8 0.0461(18) 0.0411(19) 0.0353(17) 0.0003(14) 0.0153(14) 0.0110(15) O9 0.0523(13) 0.0494(14) 0.0258(11) 0.0059(9) -0.0008(9) 0.0161(11) C9 0.0287(14) 0.0251(15) 0.0291(14) -0.0002(11) 0.0037(11) 0.0013(12) O10 0.0438(13) 0.0521(15) 0.0464(13) 0.0094(11) 0.0138(10) 0.0249(12) C10 0.0298(14) 0.0293(16) 0.0224(14) -0.0011(11) 0.0016(11) -0.0005(12) C11 0.061(2) 0.058(2) 0.0290(17) 0.0012(15) 0.0175(15) 0.0160(18) C12 0.0291(15) 0.0275(16) 0.0344(16) 0.0021(12) 0.0037(12) 0.0000(12) C13 0.0309(15) 0.0230(15) 0.0281(14) 0.0020(11) 0.0037(11) 0.0081(12) C14 0.0311(15) 0.0349(18) 0.0359(16) 0.0031(13) 0.0056(12) 0.0068(13) C15 0.0295(15) 0.0297(16) 0.0366(16) 0.0068(12) 0.0016(12) 0.0059(12) C16 0.0386(17) 0.0285(16) 0.0295(15) 0.0044(12) 0.0008(12) 0.0089(13) C17 0.0322(16) 0.0409(19) 0.0352(16) 0.0021(13) -0.0004(13) 0.0126(14) C18 0.0288(15) 0.0206(15) 0.0404(17) 0.0024(12) 0.0098(12) 0.0047(12) C19 0.0401(16) 0.0227(15) 0.0298(15) -0.0013(11) 0.0024(12) 0.0020(12) C20 0.0268(14) 0.0287(16) 0.0308(15) 0.0126(12) 0.0066(12) 0.0078(12) C21 0.0290(14) 0.0257(15) 0.0246(14) 0.0051(11) 0.0030(11) 0.0092(12) C22 0.053(2) 0.0312(18) 0.0433(18) -0.0063(14) -0.0204(15) 0.0185(15) C23 0.057(2) 0.0227(16) 0.0455(18) -0.0077(13) -0.0144(15) 0.0166(15) C24 0.0407(16) 0.0201(15) 0.0307(15) 0.0057(11) 0.0002(12) 0.0069(12) C27 0.0290(14) 0.0175(14) 0.0312(14) 0.0006(11) 0.0097(11) 0.0034(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 Cd1 O1 2.2476(18) . ? Cd1 O4 2.292(2) . ? Cd1 N1 2.353(2) . ? Cd1 O3 2.382(2) . ? Cd1 N5 2.431(2) . ? Cd1 O3 2.614(2) 2_755 ? O1 C20 1.263(3) . ? N1 C1 1.330(3) . ? N1 C2 1.344(3) . ? C1 C3 1.389(4) . ? C1 H1A 0.9300 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2 C20 1.254(3) . ? N2 C6 1.348(3) . ? N2 C3 1.417(3) . ? N2 H2B 0.8600 . ? C2 C5 1.388(4) . ? C2 H2A 0.9300 . ? O3 C18 1.276(3) . ? O3 Cd1 2.614(2) 2_755 ? N3 C9 1.344(3) . ? N3 C10 1.348(3) . ? C3 C4 1.392(3) . ? O4 C18 1.263(3) 2_755 ? N4 C12 1.353(3) . ? N4 C13 1.418(3) . ? N4 H4B 0.8600 . ? C4 C5 1.379(4) . ? C4 H4A 0.9300 . ? N5 C15 1.340(3) . ? N5 C16 1.348(3) . ? C5 H5A 0.9300 . ? C6 O9 1.229(3) . ? C6 C10 1.511(4) . ? C7 C10 1.379(4) . ? C7 C11 1.386(4) . ? C7 H7A 0.9300 . ? C8 C11 1.381(4) . ? C8 C9 1.389(4) . ? C8 H8A 0.9300 . ? C9 C12 1.511(4) . ? O10 C12 1.225(3) . ? C11 H11A 0.9300 . ? C13 C15 1.380(4) 1_565 ? C13 C14 1.395(4) . ? C14 C17 1.382(4) . ? C14 H14A 0.9300 . ? C15 C13 1.380(4) 1_545 ? C15 H15A 0.9300 . ? C16 C17 1.373(4) 1_545 ? C16 H16A 0.9300 . ? C17 C16 1.373(4) 1_565 ? C17 H17A 0.9300 . ? C18 O4 1.263(3) 2_755 ? C18 C27 1.493(4) . ? C19 C24 1.380(4) 2_765 ? C19 C27 1.389(4) . ? C19 H19A 0.9300 . ? C20 C21 1.506(3) . ? C21 C22 1.374(4) . ? C21 C23 1.384(4) . ? C22 C23 1.395(4) 2_665 ? C22 H22A 0.9300 . ? C23 C22 1.395(4) 2_665 ? C23 H23A 0.9300 . ? C24 C19 1.380(4) 2_765 ? C24 C27 1.398(4) . ? C24 H24A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 O4 140.31(8) . . ? O1 Cd1 N1 131.30(7) . . ? O4 Cd1 N1 86.11(7) . . ? O1 Cd1 O3 91.12(7) . . ? O4 Cd1 O3 92.93(7) . . ? N1 Cd1 O3 102.31(8) . . ? O1 Cd1 N5 85.93(8) . . ? O4 Cd1 N5 82.32(8) . . ? N1 Cd1 N5 87.98(8) . . ? O3 Cd1 N5 168.40(7) . . ? O1 Cd1 O3 90.75(7) . 2_755 ? O4 Cd1 O3 53.52(6) . 2_755 ? N1 Cd1 O3 137.95(7) . 2_755 ? O3 Cd1 O3 72.18(7) . 2_755 ? N5 Cd1 O3 96.61(7) . 2_755 ? C20 O1 Cd1 102.76(16) . . ? C1 N1 C2 117.8(2) . . ? C1 N1 Cd1 118.34(16) . . ? C2 N1 Cd1 123.71(18) . . ? N1 C1 C3 124.1(2) . . ? N1 C1 H1A 117.9 . . ? C3 C1 H1A 117.9 . . ? H1WA O1W H1WB 107.7 . . ? C6 N2 C3 126.7(2) . . ? C6 N2 H2B 116.7 . . ? C3 N2 H2B 116.7 . . ? N1 C2 C5 121.7(3) . . ? N1 C2 H2A 119.1 . . ? C5 C2 H2A 119.1 . . ? C18 O3 Cd1 111.80(17) . . ? C18 O3 Cd1 84.18(16) . 2_755 ? Cd1 O3 Cd1 107.82(7) . 2_755 ? C9 N3 C10 117.5(2) . . ? C1 C3 C4 117.9(2) . . ? C1 C3 N2 116.3(2) . . ? C4 C3 N2 125.8(2) . . ? C18 O4 Cd1 99.32(17) 2_755 . ? C12 N4 C13 123.5(2) . . ? C12 N4 H4B 118.2 . . ? C13 N4 H4B 118.2 . . ? C5 C4 C3 118.3(2) . . ? C5 C4 H4A 120.9 . . ? C3 C4 H4A 120.9 . . ? C15 N5 C16 117.5(2) . . ? C15 N5 Cd1 118.59(18) . . ? C16 N5 Cd1 123.89(18) . . ? C4 C5 C2 120.2(2) . . ? C4 C5 H5A 119.9 . . ? C2 C5 H5A 119.9 . . ? O9 C6 N2 124.7(3) . . ? O9 C6 C10 120.7(2) . . ? N2 C6 C10 114.5(2) . . ? C10 C7 C11 118.8(3) . . ? C10 C7 H7A 120.6 . . ? C11 C7 H7A 120.6 . . ? C11 C8 C9 118.6(3) . . ? C11 C8 H8A 120.7 . . ? C9 C8 H8A 120.7 . . ? N3 C9 C8 122.9(2) . . ? N3 C9 C12 118.8(2) . . ? C8 C9 C12 118.2(2) . . ? N3 C10 C7 123.1(3) . . ? N3 C10 C6 117.7(2) . . ? C7 C10 C6 119.2(2) . . ? C8 C11 C7 119.2(3) . . ? C8 C11 H11A 120.4 . . ? C7 C11 H11A 120.4 . . ? O10 C12 N4 124.4(3) . . ? O10 C12 C9 120.3(2) . . ? N4 C12 C9 115.3(2) . . ? C15 C13 C14 118.4(2) 1_565 . ? C15 C13 N4 118.9(2) 1_565 . ? C14 C13 N4 122.7(3) . . ? C17 C14 C13 118.2(3) . . ? C17 C14 H14A 120.9 . . ? C13 C14 H14A 120.9 . . ? N5 C15 C13 123.5(3) . 1_545 ? N5 C15 H15A 118.2 . . ? C13 C15 H15A 118.2 1_545 . ? N5 C16 C17 122.5(3) . 1_545 ? N5 C16 H16A 118.7 . . ? C17 C16 H16A 118.7 1_545 . ? C16 C17 C14 119.9(3) 1_565 . ? C16 C17 H17A 120.1 1_565 . ? C14 C17 H17A 120.1 . . ? O4 C18 O3 122.6(3) 2_755 . ? O4 C18 C27 118.4(2) 2_755 . ? O3 C18 C27 119.0(2) . . ? C24 C19 C27 120.4(3) 2_765 . ? C24 C19 H19A 119.8 2_765 . ? C27 C19 H19A 119.8 . . ? O2 C20 O1 122.6(2) . . ? O2 C20 C21 118.9(3) . . ? O1 C20 C21 118.6(2) . . ? C22 C21 C23 119.0(2) . . ? C22 C21 C20 121.1(2) . . ? C23 C21 C20 119.9(3) . . ? C21 C22 C23 120.6(3) . 2_665 ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 2_665 . ? C21 C23 C22 120.4(3) . 2_665 ? C21 C23 H23A 119.8 . . ? C22 C23 H23A 119.8 2_665 . ? C19 C24 C27 120.3(2) 2_765 . ? C19 C24 H24A 119.9 2_765 . ? C27 C24 H24A 119.9 . . ? C19 C27 C24 119.3(2) . . ? C19 C27 C18 120.5(2) . . ? C24 C27 C18 120.2(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 O4 Cd1 O1 C20 163.11(16) . . . . ? N1 Cd1 O1 C20 6.6(2) . . . . ? O3 Cd1 O1 C20 -100.94(17) . . . . ? N5 Cd1 O1 C20 90.29(18) . . . . ? O3 Cd1 O1 C20 -173.13(17) 2_755 . . . ? O1 Cd1 N1 C1 11.2(2) . . . . ? O4 Cd1 N1 C1 -154.0(2) . . . . ? O3 Cd1 N1 C1 113.9(2) . . . . ? N5 Cd1 N1 C1 -71.6(2) . . . . ? O3 Cd1 N1 C1 -169.19(18) 2_755 . . . ? O1 Cd1 N1 C2 -173.8(2) . . . . ? O4 Cd1 N1 C2 21.0(2) . . . . ? O3 Cd1 N1 C2 -71.2(2) . . . . ? N5 Cd1 N1 C2 103.4(2) . . . . ? O3 Cd1 N1 C2 5.8(3) 2_755 . . . ? C2 N1 C1 C3 1.0(4) . . . . ? Cd1 N1 C1 C3 176.3(2) . . . . ? C1 N1 C2 C5 -2.6(4) . . . . ? Cd1 N1 C2 C5 -177.6(2) . . . . ? O1 Cd1 O3 C18 0.37(19) . . . . ? O4 Cd1 O3 C18 140.88(19) . . . . ? N1 Cd1 O3 C18 -132.47(19) . . . . ? N5 Cd1 O3 C18 75.4(4) . . . . ? O3 Cd1 O3 C18 90.80(19) 2_755 . . . ? O1 Cd1 O3 Cd1 -90.43(8) . . . 2_755 ? O4 Cd1 O3 Cd1 50.08(8) . . . 2_755 ? N1 Cd1 O3 Cd1 136.73(7) . . . 2_755 ? N5 Cd1 O3 Cd1 -15.3(3) . . . 2_755 ? O3 Cd1 O3 Cd1 0.0 2_755 . . 2_755 ? N1 C1 C3 C4 1.2(4) . . . . ? N1 C1 C3 N2 -178.9(2) . . . . ? C6 N2 C3 C1 153.1(3) . . . . ? C6 N2 C3 C4 -27.0(4) . . . . ? O1 Cd1 O4 C18 26.7(2) . . . 2_755 ? N1 Cd1 O4 C18 -170.79(18) . . . 2_755 ? O3 Cd1 O4 C18 -68.64(18) . . . 2_755 ? N5 Cd1 O4 C18 100.73(18) . . . 2_755 ? O3 Cd1 O4 C18 -3.40(16) 2_755 . . 2_755 ? C1 C3 C4 C5 -1.9(4) . . . . ? N2 C3 C4 C5 178.2(3) . . . . ? O1 Cd1 N5 C15 -175.7(2) . . . . ? O4 Cd1 N5 C15 42.3(2) . . . . ? N1 Cd1 N5 C15 -44.1(2) . . . . ? O3 Cd1 N5 C15 108.7(3) . . . . ? O3 Cd1 N5 C15 94.0(2) 2_755 . . . ? O1 Cd1 N5 C16 2.5(2) . . . . ? O4 Cd1 N5 C16 -139.5(2) . . . . ? N1 Cd1 N5 C16 134.2(2) . . . . ? O3 Cd1 N5 C16 -73.1(4) . . . . ? O3 Cd1 N5 C16 -87.8(2) 2_755 . . . ? C3 C4 C5 C2 0.4(4) . . . . ? N1 C2 C5 C4 1.9(5) . . . . ? C3 N2 C6 O9 9.8(5) . . . . ? C3 N2 C6 C10 -169.1(2) . . . . ? C10 N3 C9 C8 0.2(4) . . . . ? C10 N3 C9 C12 179.0(2) . . . . ? C11 C8 C9 N3 -0.5(5) . . . . ? C11 C8 C9 C12 -179.3(3) . . . . ? C9 N3 C10 C7 0.2(4) . . . . ? C9 N3 C10 C6 178.9(2) . . . . ? C11 C7 C10 N3 -0.3(5) . . . . ? C11 C7 C10 C6 -179.0(3) . . . . ? O9 C6 C10 N3 177.0(3) . . . . ? N2 C6 C10 N3 -4.2(4) . . . . ? O9 C6 C10 C7 -4.3(4) . . . . ? N2 C6 C10 C7 174.6(3) . . . . ? C9 C8 C11 C7 0.4(5) . . . . ? C10 C7 C11 C8 -0.1(5) . . . . ? C13 N4 C12 O10 6.6(5) . . . . ? C13 N4 C12 C9 -172.1(2) . . . . ? N3 C9 C12 O10 170.4(3) . . . . ? C8 C9 C12 O10 -10.8(4) . . . . ? N3 C9 C12 N4 -10.9(4) . . . . ? C8 C9 C12 N4 167.9(3) . . . . ? C12 N4 C13 C15 134.9(3) . . . 1_565 ? C12 N4 C13 C14 -45.5(4) . . . . ? C15 C13 C14 C17 -0.9(4) 1_565 . . . ? N4 C13 C14 C17 179.5(3) . . . . ? C16 N5 C15 C13 -1.0(4) . . . 1_545 ? Cd1 N5 C15 C13 177.4(2) . . . 1_545 ? C15 N5 C16 C17 0.0(4) . . . 1_545 ? Cd1 N5 C16 C17 -178.3(2) . . . 1_545 ? C13 C14 C17 C16 0.0(4) . . . 1_565 ? Cd1 O3 C18 O4 -101.1(3) . . . 2_755 ? Cd1 O3 C18 O4 5.8(3) 2_755 . . 2_755 ? Cd1 O3 C18 C27 79.2(3) . . . . ? Cd1 O3 C18 C27 -173.9(2) 2_755 . . . ? Cd1 O1 C20 O2 2.6(3) . . . . ? Cd1 O1 C20 C21 -176.03(19) . . . . ? O2 C20 C21 C22 14.6(4) . . . . ? O1 C20 C21 C22 -166.7(3) . . . . ? O2 C20 C21 C23 -163.8(3) . . . . ? O1 C20 C21 C23 14.8(4) . . . . ? C23 C21 C22 C23 -0.6(6) . . . 2_665 ? C20 C21 C22 C23 -179.1(3) . . . 2_665 ? C22 C21 C23 C22 0.6(6) . . . 2_665 ? C20 C21 C23 C22 179.1(3) . . . 2_665 ? C24 C19 C27 C24 -0.4(5) 2_765 . . . ? C24 C19 C27 C18 179.7(3) 2_765 . . . ? C19 C24 C27 C19 0.4(5) 2_765 . . . ? C19 C24 C27 C18 -179.7(3) 2_765 . . . ? O4 C18 C27 C19 15.5(4) 2_755 . . . ? O3 C18 C27 C19 -164.8(2) . . . . ? O4 C18 C27 C24 -164.4(3) 2_755 . . . ? O3 C18 C27 C24 15.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.780 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.069 data_3 _database_code_depnum_ccdc_archive 'CCDC 905093' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 N5 O6 Zn' _chemical_formula_weight 548.83 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9526(9) _cell_length_b 12.6037(9) _cell_length_c 16.3810(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.0820(10) _cell_angle_gamma 90.00 _cell_volume 2413.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.624 _exptl_absorpt_correction_T_max 0.673 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 12710 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.26 _reflns_number_total 4373 _reflns_number_gt 3081 _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^)+(0.0757P)^2^+1.9996P] 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 4349 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 Zn1 Zn 0.29835(4) 0.16153(4) 0.31654(3) 0.03587(18) Uani 1 1 d . . . N1 N 0.1923(3) 0.2275(3) 0.2139(2) 0.0368(8) Uani 1 1 d . . . O1 O 0.1829(3) 0.0855(2) 0.35912(18) 0.0478(8) Uani 1 1 d . . . C1 C 0.0778(3) 0.2154(3) 0.2009(2) 0.0383(10) Uani 1 1 d . . . H1A H 0.0477 0.1713 0.2364 0.046 Uiso 1 1 calc R . . N2 N -0.1164(3) 0.2558(3) 0.1206(2) 0.0431(9) Uani 1 1 d . . . H2B H -0.1528 0.2748 0.0718 0.052 Uiso 1 1 calc R . . O2 O 0.4137(2) 0.2629(2) 0.37399(19) 0.0466(8) Uani 1 1 d . . . C2 C 0.2352(4) 0.2917(4) 0.1632(3) 0.0422(10) Uani 1 1 d . . . H2A H 0.3139 0.3022 0.1730 0.051 Uiso 1 1 calc R . . O3 O 0.2825(3) 0.1058(3) 0.4872(2) 0.0543(8) Uani 1 1 d . . . N3 N -0.4965(3) 0.2510(4) 0.1564(2) 0.0566(11) Uani 1 1 d . . . C3 C 0.1663(4) 0.3429(4) 0.0967(3) 0.0478(11) Uani 1 1 d . . . H3A H 0.1983 0.3853 0.0611 0.057 Uiso 1 1 calc R . . O4 O 0.2574(2) 0.3397(2) 0.39340(19) 0.0446(7) Uani 1 1 d . . . N4 N -0.4605(3) 0.0964(3) -0.1060(2) 0.0463(9) Uani 1 1 d . . . H4B H -0.3915 0.1200 -0.0939 0.056 Uiso 1 1 calc R . . C4 C 0.0497(4) 0.3303(4) 0.0838(3) 0.0437(10) Uani 1 1 d . . . H4A H 0.0019 0.3646 0.0395 0.052 Uiso 1 1 calc R . . C5 C 0.0039(3) 0.2663(3) 0.1368(2) 0.0355(9) Uani 1 1 d . . . N5 N -0.4219(3) -0.0667(3) -0.2817(2) 0.0366(8) Uani 1 1 d . . . O5 O -0.1423(3) 0.1893(4) 0.2447(2) 0.0770(12) Uani 1 1 d . . . C6 C -0.1810(4) 0.2189(4) 0.1738(3) 0.0464(11) Uani 1 1 d . . . O6 O -0.6282(3) 0.0947(3) -0.0623(2) 0.0680(11) Uani 1 1 d . . . C7 C -0.3065(3) 0.2170(4) 0.1367(3) 0.0421(10) Uani 1 1 d . . . C8 C -0.3830(4) 0.2524(4) 0.1839(3) 0.0528(12) Uani 1 1 d . . . H8A H -0.3538 0.2783 0.2372 0.063 Uiso 1 1 calc R . . C9 C -0.3500(4) 0.1752(3) 0.0585(3) 0.0417(10) Uani 1 1 d . . . H9A H -0.3006 0.1507 0.0257 0.050 Uiso 1 1 calc R . . C10 C -0.5361(4) 0.2102(4) 0.0809(3) 0.0514(12) Uani 1 1 d . . . H10A H -0.6150 0.2086 0.0615 0.062 Uiso 1 1 calc R . . C11 C -0.4681(3) 0.1698(3) 0.0289(3) 0.0414(10) Uani 1 1 d . . . C12 C -0.5275(4) 0.1188(4) -0.0505(3) 0.0445(11) Uani 1 1 d . . . C13 C -0.4915(4) 0.0392(3) -0.1809(3) 0.0401(10) Uani 1 1 d . . . C14 C -0.6025(4) 0.0268(4) -0.2245(3) 0.0537(13) Uani 1 1 d . . . H14A H -0.6632 0.0572 -0.2056 0.064 Uiso 1 1 calc R . . C15 C -0.4039(3) -0.0085(3) -0.2117(3) 0.0394(10) Uani 1 1 d . . . H15A H -0.3291 0.0004 -0.1821 0.047 Uiso 1 1 calc R . . C16 C -0.6212(4) -0.0325(4) -0.2977(3) 0.0616(15) Uani 1 1 d . . . H16A H -0.6951 -0.0414 -0.3289 0.074 Uiso 1 1 calc R . . C17 C -0.5309(4) -0.0775(4) -0.3235(3) 0.0509(12) Uani 1 1 d . . . H17A H -0.5452 -0.1175 -0.3723 0.061 Uiso 1 1 calc R . . C18 C 0.1946(3) 0.0806(3) 0.4375(3) 0.0368(10) Uani 1 1 d . . . C19 C 0.0932(3) 0.0393(3) 0.4696(2) 0.0343(9) Uani 1 1 d . . . C20 C -0.0088(4) 0.0145(5) 0.4168(3) 0.0655(16) Uani 1 1 d . . . H20A H -0.0164 0.0238 0.3596 0.079 Uiso 1 1 calc R . . C21 C -0.0999(4) -0.0239(5) 0.4473(3) 0.0649(16) Uani 1 1 d . . . H21A H -0.1678 -0.0397 0.4100 0.078 Uiso 1 1 calc R . . C22 C 0.3621(3) 0.3371(3) 0.4035(2) 0.0331(9) Uani 1 1 d . . . C23 C 0.4337(3) 0.4217(3) 0.4528(2) 0.0348(9) Uani 1 1 d . . . C24 C 0.5524(4) 0.4188(3) 0.4647(3) 0.0420(10) Uani 1 1 d . . . H24A H 0.5877 0.3648 0.4407 0.050 Uiso 1 1 calc R . . C25 C 0.6179(4) 0.4963(3) 0.5120(3) 0.0415(10) Uani 1 1 d . . . H25A H 0.6972 0.4935 0.5203 0.050 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 0.0255(3) 0.0460(3) 0.0362(3) -0.0065(2) 0.00670(19) -0.0041(2) N1 0.0251(18) 0.049(2) 0.0369(18) -0.0074(16) 0.0078(15) -0.0042(16) O1 0.0446(18) 0.063(2) 0.0378(17) -0.0026(15) 0.0140(14) -0.0146(16) C1 0.026(2) 0.050(3) 0.039(2) -0.002(2) 0.0063(18) -0.0075(19) N2 0.0226(17) 0.068(2) 0.038(2) 0.0019(18) 0.0047(15) -0.0020(17) O2 0.0324(16) 0.0446(17) 0.063(2) -0.0222(15) 0.0104(15) -0.0049(14) C2 0.024(2) 0.057(3) 0.047(3) -0.002(2) 0.0097(19) -0.005(2) O3 0.0308(17) 0.073(2) 0.056(2) 0.0004(17) 0.0019(15) -0.0122(16) N3 0.031(2) 0.087(3) 0.055(2) -0.023(2) 0.0153(18) -0.003(2) C3 0.039(3) 0.056(3) 0.051(3) 0.006(2) 0.018(2) -0.009(2) O4 0.0277(16) 0.0503(18) 0.0551(19) -0.0071(15) 0.0071(14) -0.0014(14) N4 0.0283(19) 0.061(2) 0.052(2) -0.0190(19) 0.0138(17) -0.0069(18) C4 0.035(2) 0.052(3) 0.043(2) 0.004(2) 0.0059(19) 0.000(2) C5 0.024(2) 0.046(2) 0.037(2) -0.0038(19) 0.0081(17) -0.0018(19) N5 0.0320(19) 0.0418(19) 0.0354(19) -0.0059(16) 0.0057(15) -0.0023(16) O5 0.0346(19) 0.146(4) 0.050(2) 0.027(2) 0.0090(16) -0.003(2) C6 0.027(2) 0.070(3) 0.041(3) -0.004(2) 0.006(2) -0.002(2) O6 0.0317(18) 0.106(3) 0.070(2) -0.039(2) 0.0191(16) -0.0203(19) C7 0.027(2) 0.054(3) 0.046(3) -0.004(2) 0.0111(19) -0.004(2) C8 0.035(2) 0.077(3) 0.048(3) -0.018(2) 0.012(2) -0.005(2) C9 0.029(2) 0.054(3) 0.046(3) -0.003(2) 0.0162(19) 0.000(2) C10 0.025(2) 0.074(3) 0.058(3) -0.020(3) 0.014(2) -0.007(2) C11 0.028(2) 0.050(3) 0.049(3) -0.011(2) 0.0146(19) -0.008(2) C12 0.032(2) 0.055(3) 0.049(3) -0.015(2) 0.015(2) -0.006(2) C13 0.034(2) 0.044(2) 0.043(2) -0.006(2) 0.0098(19) 0.000(2) C14 0.033(2) 0.070(3) 0.056(3) -0.013(3) 0.005(2) 0.013(2) C15 0.029(2) 0.048(3) 0.042(2) -0.005(2) 0.0086(18) -0.006(2) C16 0.036(3) 0.083(4) 0.057(3) -0.024(3) -0.011(2) 0.018(3) C17 0.044(3) 0.063(3) 0.042(3) -0.010(2) 0.000(2) 0.011(2) C18 0.031(2) 0.037(2) 0.042(2) -0.0004(19) 0.0085(19) -0.0008(19) C19 0.025(2) 0.041(2) 0.036(2) 0.0000(18) 0.0027(17) -0.0011(18) C20 0.046(3) 0.113(5) 0.034(3) 0.012(3) -0.001(2) -0.027(3) C21 0.034(3) 0.113(5) 0.041(3) 0.019(3) -0.008(2) -0.026(3) C22 0.031(2) 0.035(2) 0.034(2) 0.0000(18) 0.0079(17) -0.0040(19) C23 0.032(2) 0.033(2) 0.041(2) -0.0036(18) 0.0110(18) -0.0010(18) C24 0.032(2) 0.036(2) 0.061(3) -0.010(2) 0.014(2) -0.0008(19) C25 0.026(2) 0.042(2) 0.058(3) -0.005(2) 0.013(2) -0.0026(19) _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 O1 1.927(3) . ? Zn1 O2 1.969(3) . ? Zn1 N1 2.057(3) . ? Zn1 N5 2.071(3) 3 ? N1 C2 1.336(5) . ? N1 C1 1.348(5) . ? O1 C18 1.264(5) . ? C1 C5 1.381(6) . ? N2 C6 1.362(5) . ? N2 C5 1.412(5) . ? O2 C22 1.270(5) . ? C2 C3 1.381(6) . ? O3 C18 1.228(5) . ? N3 C10 1.332(6) . ? N3 C8 1.338(6) . ? C3 C4 1.375(6) . ? O4 C22 1.229(5) . ? N4 C12 1.361(5) . ? N4 C13 1.405(5) . ? C4 C5 1.380(6) . ? N5 C15 1.340(5) . ? N5 C17 1.346(5) . ? N5 Zn1 2.071(3) 3 ? O5 C6 1.215(5) . ? C6 C7 1.497(6) . ? O6 C12 1.217(5) . ? C7 C9 1.381(6) . ? C7 C8 1.388(6) . ? C9 C11 1.395(6) . ? C10 C11 1.392(6) . ? C11 C12 1.491(6) . ? C13 C14 1.377(6) . ? C13 C15 1.390(6) . ? C14 C16 1.390(7) . ? C16 C17 1.363(6) . ? C18 C19 1.510(6) . ? C19 C21 1.362(6) 3_556 ? C19 C20 1.375(6) . ? C20 C21 1.376(6) . ? C21 C19 1.362(6) 3_556 ? C22 C23 1.494(5) . ? C23 C25 1.389(5) 3_666 ? C23 C24 1.392(6) . ? C24 C25 1.384(6) . ? C25 C23 1.389(5) 3_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O2 129.26(13) . . ? O1 Zn1 N1 97.54(13) . . ? O2 Zn1 N1 112.23(13) . . ? O1 Zn1 N5 114.77(14) . 3 ? O2 Zn1 N5 92.17(12) . 3 ? N1 Zn1 N5 111.15(13) . 3 ? C2 N1 C1 118.6(4) . . ? C2 N1 Zn1 120.1(3) . . ? C1 N1 Zn1 121.0(3) . . ? C18 O1 Zn1 117.1(3) . . ? N1 C1 C5 122.3(4) . . ? C6 N2 C5 127.0(4) . . ? C22 O2 Zn1 108.2(2) . . ? N1 C2 C3 122.1(4) . . ? C10 N3 C8 117.0(4) . . ? C4 C3 C2 119.0(4) . . ? C12 N4 C13 127.2(4) . . ? C3 C4 C5 119.6(4) . . ? C4 C5 C1 118.3(4) . . ? C4 C5 N2 117.3(4) . . ? C1 C5 N2 124.4(4) . . ? C15 N5 C17 117.1(4) . . ? C15 N5 Zn1 123.8(3) . 3 ? C17 N5 Zn1 118.1(3) . 3 ? O5 C6 N2 124.3(4) . . ? O5 C6 C7 122.2(4) . . ? N2 C6 C7 113.5(4) . . ? C9 C7 C8 118.3(4) . . ? C9 C7 C6 122.3(4) . . ? C8 C7 C6 119.3(4) . . ? N3 C8 C7 123.3(4) . . ? C7 C9 C11 119.9(4) . . ? N3 C10 C11 124.8(4) . . ? C10 C11 C9 116.5(4) . . ? C10 C11 C12 117.3(4) . . ? C9 C11 C12 126.0(4) . . ? O6 C12 N4 122.9(4) . . ? O6 C12 C11 121.4(4) . . ? N4 C12 C11 115.6(4) . . ? C14 C13 C15 118.7(4) . . ? C14 C13 N4 124.1(4) . . ? C15 C13 N4 117.2(4) . . ? C13 C14 C16 118.2(4) . . ? N5 C15 C13 123.3(4) . . ? C17 C16 C14 119.8(4) . . ? N5 C17 C16 123.0(4) . . ? O3 C18 O1 124.0(4) . . ? O3 C18 C19 119.7(4) . . ? O1 C18 C19 116.3(4) . . ? C21 C19 C20 117.0(4) 3_556 . ? C21 C19 C18 120.9(4) 3_556 . ? C20 C19 C18 122.0(4) . . ? C19 C20 C21 121.2(4) . . ? C19 C21 C20 121.9(4) 3_556 . ? O4 C22 O2 122.0(4) . . ? O4 C22 C23 120.4(4) . . ? O2 C22 C23 117.6(3) . . ? C25 C23 C24 119.3(4) 3_666 . ? C25 C23 C22 120.1(4) 3_666 . ? C24 C23 C22 120.5(4) . . ? C25 C24 C23 120.0(4) . . ? C24 C25 C23 120.6(4) . 3_666 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.26 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.579 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.070 data_4 _database_code_depnum_ccdc_archive 'CCDC 905094' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 Cd N5 O6' _chemical_formula_weight 595.84 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1167(6) _cell_length_b 14.3657(7) _cell_length_c 15.1482(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.2610(10) _cell_angle_gamma 90.00 _cell_volume 2415.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.644 _exptl_absorpt_correction_T_max 0.669 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 15306 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.26 _reflns_number_total 5980 _reflns_number_gt 4914 _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^)+(0.0357P)^2^+1.4618P] 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 5783 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Cd1 Cd 0.307167(13) 0.290743(10) 0.789792(9) 0.02409(6) Uani 1 1 d . . . O1 O 0.45937(14) 0.21043(11) 0.86585(12) 0.0381(4) Uani 1 1 d . . . N1 N 0.17678(16) 0.22284(13) 0.68194(13) 0.0284(4) Uani 1 1 d . . . C1 C 0.39324(18) 0.14523(15) 0.88940(13) 0.0266(4) Uani 1 1 d . . . O2 O 0.28234(13) 0.14255(11) 0.86708(11) 0.0340(4) Uani 1 1 d . . . N2 N 0.43400(17) 0.42288(14) 0.78949(13) 0.0353(4) Uani 1 1 d . . . C2 C 0.44788(19) 0.06959(15) 0.94647(15) 0.0298(5) Uani 1 1 d . . . N3 N 0.47046(16) 0.60332(14) 0.62370(12) 0.0320(4) Uani 1 1 d . . . H3B H 0.4007 0.6294 0.6209 0.038 Uiso 1 1 calc R . . O3 O 0.14961(15) 0.39105(14) 0.81621(11) 0.0474(5) Uani 1 1 d . . . C3 C 0.3775(2) -0.00112(17) 0.97812(17) 0.0391(6) Uani 1 1 d . . . H3A H 0.2951 -0.0019 0.9636 0.047 Uiso 1 1 calc R . . O4 O 0.25113(15) 0.35074(13) 0.93889(11) 0.0418(4) Uani 1 1 d . . . N4 N 0.54574(17) 0.73143(15) 0.33677(13) 0.0355(4) Uani 1 1 d . . . C4 C 0.4288(2) -0.07060(18) 1.03111(18) 0.0410(6) Uani 1 1 d . . . H4A H 0.3809 -0.1180 1.0518 0.049 Uiso 1 1 calc R . . N5 N 0.13958(16) 0.76760(15) 0.40554(12) 0.0328(4) Uani 1 1 d . . . H5A H 0.1715 0.7720 0.4584 0.039 Uiso 1 1 calc R . . O5 O 0.65030(18) 0.5964(2) 0.56310(16) 0.0969(11) Uani 1 1 d . . . C5 C 0.16573(19) 0.39267(15) 0.89870(15) 0.0298(5) Uani 1 1 d . . . C6 C 0.07963(19) 0.44865(15) 0.95107(15) 0.0290(4) Uani 1 1 d . . . O6 O 0.17456(17) 0.72029(17) 0.26591(12) 0.0586(6) Uani 1 1 d . . . C7 C -0.0165(2) 0.49490(19) 0.90895(16) 0.0423(6) Uani 1 1 d . . . H7A H -0.0282 0.4919 0.8477 0.051 Uiso 1 1 calc R . . C8 C -0.0955(2) 0.54562(19) 0.95761(16) 0.0401(6) Uani 1 1 d . . . H8A H -0.1600 0.5763 0.9286 0.048 Uiso 1 1 calc R . . C9 C 0.4122(2) 0.48724(16) 0.72686(15) 0.0324(5) Uani 1 1 d . . . H9A H 0.3338 0.4941 0.7029 0.039 Uiso 1 1 calc R . . C10 C 0.5462(2) 0.41549(17) 0.82585(15) 0.0369(5) Uani 1 1 d . . . H10A H 0.5621 0.3708 0.8694 0.044 Uiso 1 1 calc R . . C11 C 0.6387(2) 0.47174(18) 0.80112(16) 0.0394(6) Uani 1 1 d . . . H11A H 0.7152 0.4656 0.8286 0.047 Uiso 1 1 calc R . . C12 C 0.6175(2) 0.53727(18) 0.73526(16) 0.0387(5) Uani 1 1 d . . . H12A H 0.6791 0.5757 0.7176 0.046 Uiso 1 1 calc R . . C13 C 0.5014(2) 0.54416(16) 0.69602(14) 0.0299(5) Uani 1 1 d . . . C14 C 0.5455(2) 0.6207(2) 0.55888(17) 0.0426(6) Uani 1 1 d . . . C15 C 0.49476(19) 0.66869(17) 0.47703(15) 0.0308(5) Uani 1 1 d . . . C16 C 0.5766(2) 0.69521(17) 0.41624(15) 0.0352(5) Uani 1 1 d . . . H16A H 0.6582 0.6874 0.4316 0.042 Uiso 1 1 calc R . . C17 C 0.37296(19) 0.68267(16) 0.45498(14) 0.0303(5) Uani 1 1 d . . . H17A H 0.3151 0.6669 0.4944 0.036 Uiso 1 1 calc R . . C18 C 0.4281(2) 0.74321(18) 0.31608(15) 0.0330(5) Uani 1 1 d . . . H18A H 0.4048 0.7678 0.2609 0.040 Uiso 1 1 calc R . . C19 C 0.33935(19) 0.72058(16) 0.37295(14) 0.0292(5) Uani 1 1 d . . . C20 C 0.2103(2) 0.73538(18) 0.34182(15) 0.0342(5) Uani 1 1 d . . . C21 C 0.2150(2) 0.14974(17) 0.63630(16) 0.0346(5) Uani 1 1 d . . . H21A H 0.2937 0.1291 0.6473 0.042 Uiso 1 1 calc R . . C22 C 0.06186(19) 0.25054(16) 0.66859(15) 0.0289(4) Uani 1 1 d . . . H22A H 0.0347 0.3010 0.7003 0.035 Uiso 1 1 calc R . . C23 C 0.1423(2) 0.10397(18) 0.57371(17) 0.0394(6) Uani 1 1 d . . . H23A H 0.1723 0.0548 0.5416 0.047 Uiso 1 1 calc R . . C24 C -0.01777(18) 0.20557(16) 0.60837(14) 0.0280(4) Uani 1 1 d . . . C25 C 0.0238(2) 0.13249(17) 0.55940(15) 0.0346(5) Uani 1 1 d . . . H25A H -0.0270 0.1028 0.5174 0.041 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 Cd1 0.01994(8) 0.02761(9) 0.02461(9) 0.00542(6) 0.00031(5) 0.00389(6) O1 0.0269(8) 0.0376(9) 0.0499(10) 0.0233(8) 0.0040(7) 0.0036(7) N1 0.0184(8) 0.0358(10) 0.0307(9) 0.0027(8) -0.0006(7) 0.0021(7) C1 0.0246(10) 0.0302(11) 0.0252(10) 0.0068(8) 0.0043(8) 0.0044(8) O2 0.0233(7) 0.0375(9) 0.0406(9) 0.0114(7) -0.0034(6) 0.0035(7) N2 0.0333(10) 0.0345(11) 0.0386(11) 0.0092(8) 0.0070(8) 0.0030(8) C2 0.0223(10) 0.0310(11) 0.0360(12) 0.0121(9) 0.0020(9) 0.0041(8) N3 0.0236(9) 0.0390(11) 0.0338(10) 0.0124(8) 0.0050(7) 0.0075(8) O3 0.0346(9) 0.0702(13) 0.0368(9) -0.0183(9) -0.0042(7) 0.0162(9) C3 0.0197(10) 0.0426(14) 0.0547(15) 0.0232(12) -0.0015(10) -0.0004(9) O4 0.0377(9) 0.0496(11) 0.0387(9) 0.0076(8) 0.0085(7) 0.0194(8) N4 0.0213(9) 0.0540(13) 0.0317(10) 0.0085(9) 0.0050(7) -0.0007(8) C4 0.0221(11) 0.0401(13) 0.0604(16) 0.0268(12) -0.0001(10) -0.0036(10) N5 0.0185(8) 0.0540(12) 0.0255(9) -0.0061(8) -0.0024(7) 0.0047(8) O5 0.0378(11) 0.186(3) 0.0694(15) 0.0730(18) 0.0247(11) 0.0524(15) C5 0.0244(10) 0.0298(11) 0.0354(12) -0.0040(9) 0.0040(9) -0.0004(8) C6 0.0228(10) 0.0308(11) 0.0335(11) -0.0042(9) 0.0021(8) 0.0020(8) O6 0.0303(9) 0.118(2) 0.0274(9) -0.0140(10) -0.0017(7) 0.0123(11) C7 0.0379(13) 0.0580(16) 0.0303(12) -0.0069(11) -0.0031(10) 0.0158(12) C8 0.0336(12) 0.0510(15) 0.0351(12) -0.0041(11) -0.0034(10) 0.0158(11) C9 0.0272(11) 0.0343(12) 0.0362(12) 0.0064(9) 0.0047(9) 0.0046(9) C10 0.0424(13) 0.0371(13) 0.0309(12) 0.0058(10) -0.0011(10) 0.0029(11) C11 0.0355(13) 0.0469(14) 0.0346(12) 0.0048(11) -0.0076(10) -0.0010(11) C12 0.0329(12) 0.0429(14) 0.0399(13) 0.0060(11) -0.0013(10) -0.0055(10) C13 0.0299(11) 0.0320(11) 0.0282(11) 0.0048(9) 0.0038(9) 0.0030(9) C14 0.0261(11) 0.0608(17) 0.0415(13) 0.0186(12) 0.0087(10) 0.0137(11) C15 0.0220(10) 0.0392(12) 0.0318(11) 0.0055(9) 0.0063(8) 0.0055(9) C16 0.0217(10) 0.0520(15) 0.0324(12) 0.0079(10) 0.0049(9) 0.0015(10) C17 0.0223(10) 0.0404(12) 0.0288(11) 0.0021(9) 0.0067(8) 0.0030(9) C18 0.0246(11) 0.0470(14) 0.0274(11) 0.0025(10) 0.0025(9) 0.0018(10) C19 0.0197(10) 0.0392(12) 0.0288(11) -0.0041(9) 0.0027(8) 0.0028(9) C20 0.0216(10) 0.0510(14) 0.0300(12) -0.0026(10) 0.0010(9) 0.0019(10) C21 0.0219(10) 0.0376(13) 0.0441(13) -0.0015(10) 0.0000(9) 0.0067(9) C22 0.0204(10) 0.0347(12) 0.0315(11) -0.0037(9) 0.0005(8) 0.0031(9) C23 0.0335(12) 0.0391(14) 0.0459(14) -0.0102(11) 0.0055(10) 0.0061(10) C24 0.0183(9) 0.0390(12) 0.0267(10) 0.0012(9) 0.0022(8) 0.0016(8) C25 0.0262(11) 0.0434(13) 0.0338(12) -0.0075(10) -0.0010(9) -0.0008(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O1 2.3021(16) . ? Cd1 O3 2.3204(17) . ? Cd1 N1 2.3350(19) . ? Cd1 N2 2.365(2) . ? Cd1 O2 2.4528(16) . ? Cd1 O4 2.5283(17) . ? Cd1 N4 2.6091(19) 3_666 ? Cd1 C1 2.720(2) . ? O1 C1 1.255(3) . ? N1 C21 1.340(3) . ? N1 C22 1.342(3) . ? C1 O2 1.260(2) . ? C1 C2 1.496(3) . ? N2 C9 1.337(3) . ? N2 C10 1.338(3) . ? C2 C3 1.384(3) . ? C2 C4 1.394(3) 3_657 ? N3 C14 1.348(3) . ? N3 C13 1.413(3) . ? O3 C5 1.252(3) . ? C3 C4 1.383(3) . ? O4 C5 1.253(3) . ? N4 C18 1.338(3) . ? N4 C16 1.338(3) . ? N4 Cd1 2.6091(19) 3_666 ? C4 C2 1.394(3) 3_657 ? N5 C20 1.360(3) . ? N5 C24 1.412(3) 3_566 ? O5 C14 1.214(3) . ? C5 C6 1.510(3) . ? C6 C7 1.383(3) . ? C6 C8 1.387(3) 3_567 ? O6 C20 1.214(3) . ? C7 C8 1.385(3) . ? C8 C6 1.387(3) 3_567 ? C9 C13 1.386(3) . ? C10 C11 1.377(3) . ? C11 C12 1.382(3) . ? C12 C13 1.394(3) . ? C14 C15 1.500(3) . ? C15 C16 1.385(3) . ? C15 C17 1.391(3) . ? C17 C19 1.388(3) . ? C18 C19 1.385(3) . ? C19 C20 1.500(3) . ? C21 C23 1.377(3) . ? C22 C24 1.393(3) . ? C23 C25 1.385(3) . ? C24 C25 1.380(3) . ? C24 N5 1.412(3) 3_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 O3 139.95(6) . . ? O1 Cd1 N1 123.37(7) . . ? O3 Cd1 N1 86.30(6) . . ? O1 Cd1 N2 88.97(6) . . ? O3 Cd1 N2 87.59(7) . . ? N1 Cd1 N2 132.88(7) . . ? O1 Cd1 O2 54.94(5) . . ? O3 Cd1 O2 110.50(6) . . ? N1 Cd1 O2 83.63(6) . . ? N2 Cd1 O2 141.35(6) . . ? O1 Cd1 O4 86.29(6) . . ? O3 Cd1 O4 53.66(6) . . ? N1 Cd1 O4 126.35(6) . . ? N2 Cd1 O4 84.57(7) . . ? O2 Cd1 O4 80.18(6) . . ? O1 Cd1 N4 80.39(6) . 3_666 ? O3 Cd1 N4 135.51(7) . 3_666 ? N1 Cd1 N4 79.92(6) . 3_666 ? N2 Cd1 N4 72.42(7) . 3_666 ? O2 Cd1 N4 109.70(6) . 3_666 ? O4 Cd1 N4 153.46(6) . 3_666 ? O1 Cd1 C1 27.35(6) . . ? O3 Cd1 C1 128.81(7) . . ? N1 Cd1 C1 104.59(7) . . ? N2 Cd1 C1 115.28(7) . . ? O2 Cd1 C1 27.59(5) . . ? O4 Cd1 C1 82.14(6) . . ? N4 Cd1 C1 95.65(6) 3_666 . ? C1 O1 Cd1 95.20(13) . . ? C21 N1 C22 118.8(2) . . ? C21 N1 Cd1 119.09(14) . . ? C22 N1 Cd1 121.95(15) . . ? O1 C1 O2 121.77(19) . . ? O1 C1 C2 118.77(19) . . ? O2 C1 C2 119.45(19) . . ? O1 C1 Cd1 57.45(11) . . ? O2 C1 Cd1 64.33(11) . . ? C2 C1 Cd1 175.90(16) . . ? C1 O2 Cd1 88.08(12) . . ? C9 N2 C10 118.3(2) . . ? C9 N2 Cd1 118.20(16) . . ? C10 N2 Cd1 118.50(16) . . ? C3 C2 C4 119.4(2) . 3_657 ? C3 C2 C1 120.95(19) . . ? C4 C2 C1 119.66(19) 3_657 . ? C14 N3 C13 122.88(19) . . ? C5 O3 Cd1 96.72(14) . . ? C4 C3 C2 120.5(2) . . ? C5 O4 Cd1 87.03(13) . . ? C18 N4 C16 117.22(19) . . ? C18 N4 Cd1 119.23(15) . 3_666 ? C16 N4 Cd1 118.29(15) . 3_666 ? C3 C4 C2 120.1(2) . 3_657 ? C20 N5 C24 125.10(19) . 3_566 ? O3 C5 O4 122.5(2) . . ? O3 C5 C6 118.4(2) . . ? O4 C5 C6 119.1(2) . . ? C7 C6 C8 118.8(2) . 3_567 ? C7 C6 C5 120.7(2) . . ? C8 C6 C5 120.5(2) 3_567 . ? C6 C7 C8 120.2(2) . . ? C7 C8 C6 120.9(2) . 3_567 ? N2 C9 C13 122.9(2) . . ? N2 C10 C11 122.3(2) . . ? C10 C11 C12 119.8(2) . . ? C11 C12 C13 118.1(2) . . ? C9 C13 C12 118.5(2) . . ? C9 C13 N3 118.0(2) . . ? C12 C13 N3 123.5(2) . . ? O5 C14 N3 122.7(2) . . ? O5 C14 C15 119.4(2) . . ? N3 C14 C15 117.90(19) . . ? C16 C15 C17 117.9(2) . . ? C16 C15 C14 116.45(19) . . ? C17 C15 C14 125.5(2) . . ? N4 C16 C15 124.1(2) . . ? C19 C17 C15 118.7(2) . . ? N4 C18 C19 123.1(2) . . ? C18 C19 C17 118.9(2) . . ? C18 C19 C20 118.3(2) . . ? C17 C19 C20 122.8(2) . . ? O6 C20 N5 124.2(2) . . ? O6 C20 C19 121.9(2) . . ? N5 C20 C19 113.97(19) . . ? N1 C21 C23 122.6(2) . . ? N1 C22 C24 121.7(2) . . ? C21 C23 C25 118.8(2) . . ? C25 C24 C22 119.0(2) . . ? C25 C24 N5 118.4(2) . 3_566 ? C22 C24 N5 122.6(2) . 3_566 ? C24 C25 C23 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.715 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.066