Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Guang Che' _publ_contact_author_address ; Department of Chemistry Jilin Normal University Siping 136000 CHINA ; _publ_contact_author_email GUANGBOCHEJL@YAHOO.COM _publ_section_title ; Syntheses, structures and photoluminescence of a series of metal-organic complexes with 1,3,5-benzenetricarboxylate and pyrazino[2,3-f][1,10]-phenanthroline ligands ; loop_ _publ_author_name 'Guang Che' 'Chun-Bo Liu' 'Bo Liu' 'Qing-Wei Wang' 'Zhan-Lin Xu' data_compound-1 _database_code_depnum_ccdc_archive 'CCDC 656590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 Co2 N8 O16, 4(H2 O)' _chemical_formula_sum 'C46 H40 Co2 N8 O20' _chemical_formula_weight 1142.72 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' Co Co 0.3494 0.9721 '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' _symmetry_space_group_name_Hall '- P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6519(15) _cell_length_b 11.885(2) _cell_length_c 13.594(3) _cell_angle_alpha 69.47(3) _cell_angle_beta 79.83(3) _cell_angle_gamma 82.01(3) _cell_volume 1135.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9166 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 586 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_T_max 0.857 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11263 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5143 _reflns_number_gt 3913 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO ' _computing_data_reduction 'PROCESS-AUTO ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0542P)^2^+0.3411P] 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 5143 _refine_ls_number_parameters 379 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.4426(3) 0.3038(2) 0.58426(19) 0.0282(6) Uani 1 1 d . . . H1 H 0.3891 0.3699 0.5355 0.034 Uiso 1 1 calc R . . C2 C 0.5024(4) 0.2026(3) 0.5563(2) 0.0315(6) Uani 1 1 d . . . H2 H 0.4869 0.2011 0.4905 0.038 Uiso 1 1 calc R . . C3 C 0.5843(4) 0.1046(3) 0.6255(2) 0.0307(6) Uani 1 1 d . . . H3 H 0.6264 0.0364 0.6071 0.037 Uiso 1 1 calc R . . C4 C 0.6037(3) 0.1091(2) 0.72549(18) 0.0242(5) Uani 1 1 d . . . C5 C 0.5378(3) 0.2139(2) 0.74688(18) 0.0221(5) Uani 1 1 d . . . C6 C 0.5558(3) 0.2258(2) 0.84833(18) 0.0228(5) Uani 1 1 d . . . C7 C 0.6490(3) 0.1343(2) 0.92092(19) 0.0286(6) Uani 1 1 d . . . C8 C 0.6701(4) 0.1543(3) 1.0142(2) 0.0368(7) Uani 1 1 d . . . H8 H 0.7320 0.0964 1.0648 0.044 Uiso 1 1 calc R . . C9 C 0.5987(4) 0.2594(3) 1.0291(2) 0.0419(7) Uani 1 1 d . . . H9 H 0.6139 0.2745 1.0896 0.050 Uiso 1 1 calc R . . C10 C 0.5032(4) 0.3440(3) 0.9540(2) 0.0355(6) Uani 1 1 d . . . H10 H 0.4530 0.4146 0.9661 0.043 Uiso 1 1 calc R . . C11 C 0.6929(3) 0.0106(2) 0.8034(2) 0.0286(5) Uani 1 1 d . . . C12 C 0.7167(3) 0.0252(2) 0.8985(2) 0.0295(6) Uani 1 1 d . . . C13 C 0.8570(4) -0.1634(3) 0.9501(3) 0.0472(8) Uani 1 1 d . . . H13 H 0.9160 -0.2263 0.9987 0.057 Uiso 1 1 calc R . . C14 C 0.8333(4) -0.1774(3) 0.8565(3) 0.0463(8) Uani 1 1 d . . . H14 H 0.8764 -0.2494 0.8448 0.056 Uiso 1 1 calc R . . C15 C -0.0164(3) 0.3697(2) 0.75445(18) 0.0246(5) Uani 1 1 d . . . C16 C -0.0108(3) 0.3006(2) 0.67999(18) 0.0235(5) Uani 1 1 d . . . C17 C 0.0720(3) 0.1848(2) 0.70388(18) 0.0243(5) Uani 1 1 d . . . H17 H 0.1206 0.1492 0.7668 0.029 Uiso 1 1 calc R . . C18 C 0.0824(3) 0.1218(2) 0.63371(19) 0.0245(5) Uani 1 1 d . . . C19 C 0.1628(4) -0.0049(2) 0.66181(19) 0.0272(5) Uani 1 1 d . . . C20 C 0.0135(3) 0.1764(2) 0.53864(19) 0.0262(5) Uani 1 1 d . . . H20 H 0.0248 0.1352 0.4907 0.031 Uiso 1 1 calc R . . C21 C -0.0721(3) 0.2919(2) 0.51435(18) 0.0234(5) Uani 1 1 d . . . C22 C -0.1552(3) 0.3468(2) 0.41351(19) 0.0246(5) Uani 1 1 d . . . C23 C -0.0852(3) 0.3533(2) 0.58616(18) 0.0236(5) Uani 1 1 d . . . H23 H -0.1440 0.4300 0.5713 0.028 Uiso 1 1 calc R . . N1 N 0.4582(3) 0.31090(19) 0.67802(15) 0.0237(4) Uani 1 1 d . . . N2 N 0.4808(3) 0.3277(2) 0.86513(16) 0.0260(5) Uani 1 1 d . . . N3 N 0.7509(3) -0.0916(2) 0.78269(19) 0.0382(6) Uani 1 1 d . . . N4 N 0.7996(3) -0.0648(2) 0.97318(19) 0.0409(6) Uani 1 1 d . . . O1 O 0.1142(2) 0.34835(16) 0.80615(13) 0.0268(4) Uani 1 1 d . . . O2 O -0.1480(3) 0.4416(2) 0.76299(16) 0.0422(5) Uani 1 1 d . . . O1W O 0.2194(3) 0.5645(2) 0.83089(16) 0.0395(5) Uani 1 1 d D . . O3 O 0.2207(3) -0.06051(18) 0.74375(15) 0.0401(5) Uani 1 1 d . . . O2W O 0.5551(3) 0.5532(2) 0.68381(16) 0.0362(5) Uani 1 1 d D . . O4 O 0.1623(3) -0.0511(2) 0.58633(17) 0.0455(6) Uani 1 1 d . . . O3W O 0.5332(4) 0.7853(2) 0.6964(2) 0.0516(6) Uani 1 1 d D . . O5 O -0.1601(3) 0.28184(17) 0.35800(14) 0.0367(5) Uani 1 1 d . . . O4W O -0.1363(4) 0.5227(3) 0.9218(2) 0.0643(7) Uani 1 1 d D . . O6 O -0.2170(2) 0.45462(16) 0.39036(13) 0.0277(4) Uani 1 1 d . . . Co1 Co 0.34061(5) 0.44622(3) 0.74209(3) 0.02398(11) Uani 1 1 d . . . H4A H 0.173(6) -0.123(4) 0.606(4) 0.083(15) Uiso 1 1 d . . . HW11 H 0.112(4) 0.540(4) 0.849(3) 0.093(17) Uiso 1 1 d D . . HW12 H 0.209(6) 0.628(3) 0.775(3) 0.102(17) Uiso 1 1 d D . . HW21 H 0.651(3) 0.515(3) 0.704(3) 0.066(12) Uiso 1 1 d D . . HW22 H 0.541(4) 0.6216(19) 0.691(3) 0.054(11) Uiso 1 1 d D . . HW31 H 0.625(4) 0.808(5) 0.709(4) 0.12(2) Uiso 1 1 d D . . HW32 H 0.438(4) 0.821(6) 0.721(5) 0.16(3) Uiso 1 1 d D . . HW41 H -0.14(10) 0.49(2) 0.873(8) 1.5(6) Uiso 1 1 d D . . HW42 H -0.155(19) 0.467(9) 0.983(5) 0.38(8) 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 C1 0.0282(14) 0.0325(15) 0.0231(12) -0.0082(10) -0.0069(10) 0.0017(11) C2 0.0354(15) 0.0390(16) 0.0231(12) -0.0117(11) -0.0073(10) -0.0052(12) C3 0.0346(15) 0.0296(15) 0.0306(13) -0.0149(11) 0.0002(10) -0.0045(12) C4 0.0223(12) 0.0222(13) 0.0249(12) -0.0041(9) -0.0021(9) -0.0025(10) C5 0.0204(12) 0.0233(13) 0.0215(11) -0.0057(9) -0.0045(9) -0.0004(10) C6 0.0222(12) 0.0250(13) 0.0204(11) -0.0049(9) -0.0053(9) -0.0035(10) C7 0.0273(14) 0.0292(14) 0.0251(13) -0.0016(10) -0.0082(10) -0.0017(11) C8 0.0389(17) 0.0428(18) 0.0259(14) -0.0031(12) -0.0168(11) -0.0004(13) C9 0.0521(19) 0.052(2) 0.0252(14) -0.0151(13) -0.0157(12) 0.0014(15) C10 0.0369(16) 0.0433(18) 0.0325(14) -0.0195(12) -0.0090(11) -0.0001(13) C11 0.0256(14) 0.0232(14) 0.0330(14) -0.0050(10) -0.0036(10) -0.0008(11) C12 0.0236(13) 0.0267(14) 0.0324(14) -0.0012(10) -0.0081(10) -0.0010(11) C13 0.0424(19) 0.0308(18) 0.055(2) 0.0024(14) -0.0157(14) 0.0084(14) C14 0.0428(19) 0.0274(16) 0.060(2) -0.0074(14) -0.0099(14) 0.0087(13) C15 0.0247(13) 0.0259(13) 0.0235(12) -0.0087(10) -0.0049(9) 0.0000(10) C16 0.0214(12) 0.0244(13) 0.0267(12) -0.0090(10) -0.0063(9) -0.0029(10) C17 0.0242(13) 0.0261(13) 0.0221(12) -0.0055(10) -0.0079(9) -0.0013(10) C18 0.0249(13) 0.0212(13) 0.0277(12) -0.0060(10) -0.0095(9) -0.0014(10) C19 0.0308(14) 0.0223(13) 0.0289(13) -0.0069(10) -0.0111(10) 0.0007(11) C20 0.0310(14) 0.0216(13) 0.0298(13) -0.0102(10) -0.0124(10) -0.0003(10) C21 0.0249(13) 0.0212(13) 0.0240(12) -0.0050(9) -0.0087(9) -0.0011(10) C22 0.0267(13) 0.0197(13) 0.0268(12) -0.0053(9) -0.0083(9) -0.0009(10) C23 0.0232(13) 0.0193(12) 0.0279(12) -0.0062(9) -0.0085(9) 0.0014(10) N1 0.0235(11) 0.0237(11) 0.0232(10) -0.0062(8) -0.0071(8) 0.0011(8) N2 0.0275(12) 0.0271(12) 0.0257(11) -0.0097(9) -0.0091(8) -0.0003(9) N3 0.0413(15) 0.0255(13) 0.0451(14) -0.0087(10) -0.0104(11) 0.0041(11) N4 0.0389(15) 0.0327(14) 0.0417(14) 0.0027(10) -0.0168(11) 0.0023(11) O1 0.0276(10) 0.0285(10) 0.0269(9) -0.0096(7) -0.0123(7) 0.0007(8) O2 0.0337(11) 0.0547(14) 0.0492(12) -0.0329(11) -0.0171(9) 0.0162(10) O1W 0.0559(15) 0.0330(12) 0.0326(11) -0.0138(9) -0.0149(9) 0.0051(10) O3 0.0575(14) 0.0297(11) 0.0352(11) -0.0089(8) -0.0272(9) 0.0107(9) O2W 0.0317(12) 0.0301(12) 0.0472(12) -0.0100(9) -0.0146(9) 0.0006(9) O4 0.0804(18) 0.0224(11) 0.0408(12) -0.0135(9) -0.0333(11) 0.0119(11) O3W 0.0578(16) 0.0439(14) 0.0637(15) -0.0260(12) -0.0234(12) 0.0020(12) O5 0.0628(14) 0.0223(10) 0.0298(10) -0.0100(8) -0.0228(9) 0.0047(9) O4W 0.077(2) 0.0643(18) 0.0599(16) -0.0335(14) -0.0051(13) -0.0029(15) O6 0.0362(10) 0.0214(9) 0.0274(9) -0.0077(7) -0.0155(7) 0.0042(8) Co1 0.02584(19) 0.02218(19) 0.02603(19) -0.00909(13) -0.01173(12) 0.00412(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.333(3) . ? C1 C2 1.380(4) . ? C1 H1 0.9300 . ? C2 C3 1.368(4) . ? C2 H2 0.9300 . ? C3 C4 1.413(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(4) . ? C4 C11 1.457(4) . ? C5 N1 1.351(3) . ? C5 C6 1.466(3) . ? C6 N2 1.342(3) . ? C6 C7 1.394(3) . ? C7 C8 1.408(4) . ? C7 C12 1.441(4) . ? C8 C9 1.359(4) . ? C8 H8 0.9300 . ? C9 C10 1.389(4) . ? C9 H9 0.9300 . ? C10 N2 1.331(3) . ? C10 H10 0.9300 . ? C11 N3 1.341(4) . ? C11 C12 1.409(4) . ? C12 N4 1.362(3) . ? C13 N4 1.315(4) . ? C13 C14 1.386(5) . ? C13 H13 0.9300 . ? C14 N3 1.330(4) . ? C14 H14 0.9300 . ? C15 O2 1.244(3) . ? C15 O1 1.269(3) . ? C15 C16 1.503(3) . ? C16 C17 1.385(4) . ? C16 C23 1.393(3) . ? C17 C18 1.391(3) . ? C17 H17 0.9300 . ? C18 C20 1.388(3) . ? C18 C19 1.489(4) . ? C19 O3 1.204(3) . ? C19 O4 1.323(3) . ? C20 C21 1.389(4) . ? C20 H20 0.9300 . ? C21 C23 1.393(3) . ? C21 C22 1.508(3) . ? C22 O6 1.251(3) . ? C22 O5 1.263(3) . ? C23 H23 0.9300 . ? N1 Co1 2.112(2) . ? N2 Co1 2.120(2) . ? O1 Co1 2.1048(19) . ? O1W Co1 2.174(2) . ? O1W HW11 0.877(19) . ? O1W HW12 0.871(19) . ? O2W Co1 2.087(2) . ? O2W HW21 0.841(18) . ? O2W HW22 0.843(17) . ? O4 H4A 0.80(5) . ? O3W HW31 0.849(19) . ? O3W HW32 0.863(19) . ? O4W HW41 0.9(2) . ? O4W HW42 0.87(2) . ? O6 Co1 2.0805(18) 2_566 ? Co1 O6 2.0805(18) 2_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 N1 C1 C2 122.9(2) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 120.0(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 117.2(2) . . ? C5 C4 C11 120.0(2) . . ? C3 C4 C11 122.7(2) . . ? N1 C5 C4 124.0(2) . . ? N1 C5 C6 115.8(2) . . ? C4 C5 C6 120.2(2) . . ? N2 C6 C7 123.5(2) . . ? N2 C6 C5 116.6(2) . . ? C7 C6 C5 119.9(2) . . ? C6 C7 C8 117.1(3) . . ? C6 C7 C12 119.5(2) . . ? C8 C7 C12 123.4(2) . . ? C9 C8 C7 119.1(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.9(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? N2 C10 C9 122.4(3) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N3 C11 C12 121.6(2) . . ? N3 C11 C4 119.2(2) . . ? C12 C11 C4 119.2(2) . . ? N4 C12 C11 120.9(3) . . ? N4 C12 C7 118.2(2) . . ? C11 C12 C7 120.9(2) . . ? N4 C13 C14 122.8(3) . . ? N4 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? N3 C14 C13 122.4(3) . . ? N3 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? O2 C15 O1 124.4(2) . . ? O2 C15 C16 118.7(2) . . ? O1 C15 C16 116.9(2) . . ? C17 C16 C23 119.9(2) . . ? C17 C16 C15 119.7(2) . . ? C23 C16 C15 120.4(2) . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C20 C18 C17 119.8(2) . . ? C20 C18 C19 120.1(2) . . ? C17 C18 C19 120.1(2) . . ? O3 C19 O4 123.3(3) . . ? O3 C19 C18 124.6(2) . . ? O4 C19 C18 112.2(2) . . ? C18 C20 C21 120.7(2) . . ? C18 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C20 C21 C23 119.0(2) . . ? C20 C21 C22 119.9(2) . . ? C23 C21 C22 121.1(2) . . ? O6 C22 O5 123.8(2) . . ? O6 C22 C21 117.6(2) . . ? O5 C22 C21 118.6(2) . . ? C16 C23 C21 120.5(2) . . ? C16 C23 H23 119.7 . . ? C21 C23 H23 119.7 . . ? C1 N1 C5 117.3(2) . . ? C1 N1 Co1 127.54(17) . . ? C5 N1 Co1 114.55(16) . . ? C10 N2 C6 118.0(2) . . ? C10 N2 Co1 127.6(2) . . ? C6 N2 Co1 114.39(15) . . ? C14 N3 C11 116.2(3) . . ? C13 N4 C12 116.2(3) . . ? C15 O1 Co1 120.39(16) . . ? Co1 O1W HW11 99(3) . . ? Co1 O1W HW12 94(3) . . ? HW11 O1W HW12 103(3) . . ? Co1 O2W HW21 112(3) . . ? Co1 O2W HW22 117(2) . . ? HW21 O2W HW22 112(3) . . ? C19 O4 H4A 114(3) . . ? HW31 O3W HW32 110(3) . . ? HW41 O4W HW42 109(4) . . ? C22 O6 Co1 126.33(16) . 2_566 ? O6 Co1 O2W 90.59(8) 2_566 . ? O6 Co1 O1 89.11(7) 2_566 . ? O2W Co1 O1 175.54(8) . . ? O6 Co1 N1 93.97(8) 2_566 . ? O2W Co1 N1 95.28(9) . . ? O1 Co1 N1 89.18(8) . . ? O6 Co1 N2 171.77(8) 2_566 . ? O2W Co1 N2 90.20(9) . . ? O1 Co1 N2 90.73(8) . . ? N1 Co1 N2 77.79(8) . . ? O6 Co1 O1W 93.45(8) 2_566 . ? O2W Co1 O1W 88.82(10) . . ? O1 Co1 O1W 86.75(9) . . ? N1 Co1 O1W 171.47(8) . . ? N2 Co1 O1W 94.76(8) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.104 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.082 # Attachment 'compound-2.cif' data_compound-2 _database_code_depnum_ccdc_archive 'CCDC 656591' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H14 Mn N4 O7' _chemical_formula_sum 'C23 H14 Mn N4 O7' _chemical_formula_weight 513.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.160(5) _cell_length_b 13.073(4) _cell_length_c 18.365(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3879.9(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3836 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 26.1 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.778 _exptl_absorpt_correction_T_max 0.868 _exptl_absorpt_process_details '(SAINT; Bruker, 1998)' _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 'Bruker APEX CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 19795 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.10 _reflns_number_total 3836 _reflns_number_gt 2721 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material 'SHELXTL (Bruker, 1998)' _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^)+(0.0511P)^2^+0.7301P] 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 3836 _refine_ls_number_parameters 325 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.55175(16) 0.0690(2) 0.15495(15) 0.0305(6) Uani 1 1 d . . . C2 C 0.46389(15) 0.0679(2) 0.12922(14) 0.0259(6) Uani 1 1 d . . . C3 C 0.40161(15) 0.0531(2) 0.17983(14) 0.0274(6) Uani 1 1 d . . . H3 H 0.4155 0.0400 0.2281 0.033 Uiso 1 1 calc R . . C4 C 0.31892(14) 0.05741(19) 0.16006(14) 0.0238(6) Uani 1 1 d . . . C5 C 0.25487(15) 0.0499(2) 0.21917(14) 0.0269(6) Uani 1 1 d . . . C6 C 0.29835(15) 0.07117(19) 0.08709(13) 0.0239(6) Uani 1 1 d . . . H6 H 0.2431 0.0710 0.0730 0.029 Uiso 1 1 calc R . . C7 C 0.36016(15) 0.08528(19) 0.03501(13) 0.0249(6) Uani 1 1 d . . . C8 C 0.33830(17) 0.1037(2) -0.04393(14) 0.0312(6) Uani 1 1 d . . . C9 C 0.44263(15) 0.0853(2) 0.05684(14) 0.0270(6) Uani 1 1 d . . . H9 H 0.4840 0.0970 0.0227 0.032 Uiso 1 1 calc R . . C10 C 0.66471(17) 0.1731(2) -0.03792(16) 0.0377(7) Uani 1 1 d . . . H10 H 0.6155 0.1730 -0.0117 0.045 Uiso 1 1 calc R . . C11 C 0.66142(18) 0.1964(2) -0.11201(15) 0.0396(7) Uani 1 1 d . . . H11 H 0.6113 0.2113 -0.1345 0.048 Uiso 1 1 calc R . . C12 C 0.73417(18) 0.1966(2) -0.15115(16) 0.0372(7) Uani 1 1 d . . . H12 H 0.7337 0.2105 -0.2008 0.045 Uiso 1 1 calc R . . C13 C 0.80851(17) 0.1758(2) -0.11571(14) 0.0308(6) Uani 1 1 d . . . C14 C 0.80579(16) 0.1530(2) -0.04123(14) 0.0287(6) Uani 1 1 d . . . C15 C 0.88144(16) 0.1323(2) -0.00150(14) 0.0276(6) Uani 1 1 d . . . C16 C 0.94319(18) 0.0893(2) 0.10724(15) 0.0360(7) Uani 1 1 d . . . H16 H 0.9388 0.0705 0.1559 0.043 Uiso 1 1 calc R . . C17 C 1.02167(17) 0.1006(2) 0.07755(16) 0.0364(7) Uani 1 1 d . . . H17 H 1.0684 0.0913 0.1063 0.044 Uiso 1 1 calc R . . C18 C 1.02945(17) 0.1252(2) 0.00590(15) 0.0349(7) Uani 1 1 d . . . H18 H 1.0816 0.1314 -0.0151 0.042 Uiso 1 1 calc R . . C19 C 0.95835(16) 0.1409(2) -0.03577(14) 0.0300(6) Uani 1 1 d . . . C20 C 0.96115(17) 0.1628(2) -0.11383(14) 0.0322(6) Uani 1 1 d . . . C21 C 0.88734(17) 0.1779(2) -0.15276(14) 0.0310(6) Uani 1 1 d . . . C22 C 0.9624(2) 0.1965(3) -0.25638(17) 0.0492(8) Uani 1 1 d . . . H24 H 0.9660 0.2059 -0.3065 0.059 Uiso 1 1 calc R . . C23 C 1.0349(2) 0.1840(3) -0.21711(17) 0.0499(9) Uani 1 1 d . . . H25 H 1.0851 0.1877 -0.2417 0.060 Uiso 1 1 calc R . . N1 N 0.73405(13) 0.15125(17) -0.00287(12) 0.0312(5) Uani 1 1 d . . . N2 N 0.87398(13) 0.10417(18) 0.06957(11) 0.0314(5) Uani 1 1 d . . . N3 N 0.88875(15) 0.1956(2) -0.22572(13) 0.0405(6) Uani 1 1 d . . . N4 N 1.03580(15) 0.1669(2) -0.14624(13) 0.0427(6) Uani 1 1 d . . . O1 O 0.56075(11) 0.04767(18) 0.22212(11) 0.0487(6) Uani 1 1 d . . . O2 O 0.60803(11) 0.09216(16) 0.11281(10) 0.0378(5) Uani 1 1 d . . . O1W O 0.74340(14) 0.24556(17) 0.15753(12) 0.0490(6) Uani 1 1 d D . . HW11 H 0.7087(15) 0.280(2) 0.137(2) 0.073 Uiso 1 1 d D . . HW12 H 0.7871(13) 0.277(2) 0.163(2) 0.073 Uiso 1 1 d D . . O3 O 0.38788(15) 0.15141(18) -0.08174(11) 0.0563(7) Uani 1 1 d . . . O4 O 0.26933(12) 0.06707(15) -0.06584(10) 0.0376(5) Uani 1 1 d . . . O5 O 0.18021(11) 0.05931(17) 0.19911(10) 0.0413(6) Uani 1 1 d . . . H5 H 0.124(2) 0.056(2) 0.2454(18) 0.062 Uiso 1 1 d . . . O6 O 0.27809(11) 0.03776(17) 0.28246(10) 0.0385(5) Uani 1 1 d . . . Mn1 Mn 0.74166(2) 0.08336(3) 0.11122(2) 0.03069(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0240(14) 0.0370(17) 0.0304(16) -0.0057(12) 0.0009(12) 0.0027(12) C2 0.0193(13) 0.0333(16) 0.0249(14) -0.0024(11) -0.0002(10) -0.0010(11) C3 0.0250(14) 0.0396(17) 0.0177(13) -0.0014(12) -0.0011(10) 0.0008(12) C4 0.0190(13) 0.0308(15) 0.0216(13) -0.0009(11) -0.0005(10) -0.0001(11) C5 0.0237(14) 0.0338(15) 0.0230(14) -0.0009(12) 0.0019(11) -0.0005(11) C6 0.0179(12) 0.0321(15) 0.0218(13) -0.0019(11) -0.0035(10) -0.0002(11) C7 0.0265(13) 0.0288(14) 0.0193(13) 0.0001(11) 0.0008(10) -0.0009(12) C8 0.0382(17) 0.0347(16) 0.0206(14) -0.0033(12) -0.0026(12) 0.0057(13) C9 0.0211(13) 0.0367(15) 0.0231(14) -0.0018(12) 0.0057(10) -0.0005(12) C10 0.0302(15) 0.0438(18) 0.0392(18) 0.0022(14) -0.0009(13) 0.0055(13) C11 0.0401(17) 0.0445(18) 0.0343(17) 0.0020(14) -0.0106(14) 0.0069(14) C12 0.0475(18) 0.0401(18) 0.0240(15) 0.0005(13) -0.0071(13) -0.0002(14) C13 0.0383(16) 0.0309(16) 0.0231(14) -0.0019(12) 0.0005(12) -0.0027(12) C14 0.0328(16) 0.0286(15) 0.0249(14) 0.0010(11) 0.0000(12) -0.0013(12) C15 0.0312(15) 0.0306(15) 0.0211(14) -0.0009(12) 0.0013(11) -0.0026(12) C16 0.0370(16) 0.0475(18) 0.0235(15) 0.0025(13) -0.0024(12) -0.0031(14) C17 0.0293(15) 0.0457(19) 0.0342(16) -0.0017(14) -0.0070(12) -0.0023(13) C18 0.0267(15) 0.0424(18) 0.0357(17) -0.0025(14) 0.0033(12) -0.0033(13) C19 0.0333(15) 0.0298(16) 0.0269(15) -0.0011(12) 0.0018(12) -0.0014(12) C20 0.0370(16) 0.0330(16) 0.0267(15) -0.0010(12) 0.0058(12) -0.0054(13) C21 0.0406(17) 0.0311(16) 0.0214(14) -0.0025(12) 0.0014(12) -0.0045(13) C22 0.064(2) 0.059(2) 0.0248(16) 0.0017(15) 0.0108(15) -0.0071(18) C23 0.050(2) 0.068(2) 0.0320(18) -0.0008(16) 0.0149(15) -0.0075(17) N1 0.0270(12) 0.0407(14) 0.0258(12) 0.0025(10) 0.0015(9) 0.0019(10) N2 0.0319(13) 0.0431(15) 0.0192(12) 0.0031(10) 0.0011(9) -0.0004(11) N3 0.0490(15) 0.0471(16) 0.0253(13) 0.0005(11) 0.0055(11) -0.0053(13) N4 0.0411(15) 0.0546(17) 0.0322(14) 0.0006(12) 0.0102(12) -0.0065(12) O1 0.0227(10) 0.0916(18) 0.0317(12) 0.0053(11) -0.0083(9) -0.0050(10) O2 0.0187(9) 0.0566(14) 0.0381(12) 0.0008(10) 0.0029(8) -0.0006(9) O1W 0.0524(14) 0.0513(15) 0.0434(14) 0.0012(11) 0.0059(11) -0.0034(12) O3 0.0746(16) 0.0680(17) 0.0262(12) 0.0089(11) 0.0030(11) -0.0242(13) O4 0.0368(11) 0.0499(13) 0.0260(11) -0.0062(9) -0.0118(8) 0.0070(9) O5 0.0184(10) 0.0774(17) 0.0282(11) 0.0025(10) 0.0035(8) 0.0005(9) O6 0.0313(11) 0.0661(14) 0.0182(10) 0.0015(9) 0.0029(8) 0.0035(10) Mn1 0.0228(2) 0.0490(3) 0.0202(2) 0.00091(19) 0.00196(16) -0.00179(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 C1 O2 1.232(3) . ? C1 O1 1.273(3) . ? C1 C2 1.496(3) . ? C2 C3 1.383(3) . ? C2 C9 1.392(3) . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C6 1.392(4) . ? C4 C5 1.503(3) . ? C5 O6 1.232(3) . ? C5 O5 1.268(3) . ? C6 C7 1.395(3) . ? C6 H6 0.9300 . ? C7 C9 1.392(3) . ? C7 C8 1.511(4) . ? C8 O3 1.231(3) . ? C8 O4 1.278(3) . ? C9 H9 0.9300 . ? C10 N1 1.323(3) . ? C10 C11 1.395(4) . ? C10 H10 0.9300 . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.393(4) . ? C12 H12 0.9300 . ? C13 C14 1.401(4) . ? C13 C21 1.444(4) . ? C14 N1 1.357(3) . ? C14 C15 1.449(4) . ? C15 N2 1.361(3) . ? C15 C19 1.398(4) . ? C16 N2 1.329(3) . ? C16 C17 1.388(4) . ? C16 H16 0.9300 . ? C17 C18 1.360(4) . ? C17 H17 0.9300 . ? C18 C19 1.396(4) . ? C18 H18 0.9300 . ? C19 C20 1.463(4) . ? C20 N4 1.346(3) . ? C20 C21 1.404(4) . ? C21 N3 1.360(3) . ? C22 N3 1.317(4) . ? C22 C23 1.385(5) . ? C22 H24 0.9300 . ? C23 N4 1.321(4) . ? C23 H25 0.9300 . ? N1 Mn1 2.279(2) . ? N2 Mn1 2.287(2) . ? O2 Mn1 2.1628(19) . ? O1W Mn1 2.285(2) . ? O1W HW11 0.810(17) . ? O1W HW12 0.823(17) . ? O4 Mn1 2.143(2) 5_655 ? O5 H5 1.24(3) . ? O6 Mn1 2.1247(19) 6_556 ? Mn1 O6 2.1247(19) 6_656 ? Mn1 O4 2.143(2) 5_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.3(2) . . ? O2 C1 C2 120.3(2) . . ? O1 C1 C2 114.4(2) . . ? C3 C2 C9 119.0(2) . . ? C3 C2 C1 118.6(2) . . ? C9 C2 C1 122.3(2) . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C6 119.2(2) . . ? C3 C4 C5 118.2(2) . . ? C6 C4 C5 122.6(2) . . ? O6 C5 O5 125.2(2) . . ? O6 C5 C4 118.7(2) . . ? O5 C5 C4 116.1(2) . . ? C4 C6 C7 120.4(2) . . ? C4 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C9 C7 C6 119.2(2) . . ? C9 C7 C8 120.0(2) . . ? C6 C7 C8 120.7(2) . . ? O3 C8 O4 125.5(3) . . ? O3 C8 C7 118.0(3) . . ? O4 C8 C7 116.5(2) . . ? C2 C9 C7 120.8(2) . . ? C2 C9 H9 119.6 . . ? C7 C9 H9 119.6 . . ? N1 C10 C11 123.6(3) . . ? N1 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C12 C11 C10 118.5(3) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C13 119.5(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 118.1(2) . . ? C12 C13 C21 122.5(3) . . ? C14 C13 C21 119.5(2) . . ? N1 C14 C13 122.5(2) . . ? N1 C14 C15 117.1(2) . . ? C13 C14 C15 120.3(2) . . ? N2 C15 C19 122.2(2) . . ? N2 C15 C14 117.3(2) . . ? C19 C15 C14 120.5(2) . . ? N2 C16 C17 123.3(3) . . ? N2 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 119.3(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C15 118.2(2) . . ? C18 C19 C20 122.7(2) . . ? C15 C19 C20 119.0(2) . . ? N4 C20 C21 122.0(3) . . ? N4 C20 C19 118.0(3) . . ? C21 C20 C19 120.0(2) . . ? N3 C21 C20 120.7(3) . . ? N3 C21 C13 118.8(2) . . ? C20 C21 C13 120.4(2) . . ? N3 C22 C23 122.7(3) . . ? N3 C22 H24 118.6 . . ? C23 C22 H24 118.6 . . ? N4 C23 C22 122.8(3) . . ? N4 C23 H25 118.6 . . ? C22 C23 H25 118.6 . . ? C10 N1 C14 117.9(2) . . ? C10 N1 Mn1 125.24(19) . . ? C14 N1 Mn1 115.97(17) . . ? C16 N2 C15 117.6(2) . . ? C16 N2 Mn1 126.53(18) . . ? C15 N2 Mn1 115.82(17) . . ? C22 N3 C21 116.0(3) . . ? C23 N4 C20 115.6(3) . . ? C1 O2 Mn1 137.09(18) . . ? Mn1 O1W HW11 110(3) . . ? Mn1 O1W HW12 121(3) . . ? HW11 O1W HW12 112(3) . . ? C8 O4 Mn1 122.55(17) . 5_655 ? C5 O5 H5 119.4(15) . . ? C5 O6 Mn1 138.31(18) . 6_556 ? O6 Mn1 O4 97.05(8) 6_656 5_655 ? O6 Mn1 O2 106.21(7) 6_656 . ? O4 Mn1 O2 88.36(7) 5_655 . ? O6 Mn1 N1 165.74(8) 6_656 . ? O4 Mn1 N1 89.74(8) 5_655 . ? O2 Mn1 N1 86.43(7) . . ? O6 Mn1 O1W 85.12(8) 6_656 . ? O4 Mn1 O1W 175.80(8) 5_655 . ? O2 Mn1 O1W 87.58(8) . . ? N1 Mn1 O1W 88.94(8) . . ? O6 Mn1 N2 94.68(7) 6_656 . ? O4 Mn1 N2 93.24(8) 5_655 . ? O2 Mn1 N2 158.70(8) . . ? N1 Mn1 N2 72.35(8) . . ? O1W Mn1 N2 90.15(8) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.273 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.061 # Attachment 'compound-3.cif' data_compound-3 _database_code_depnum_ccdc_archive 'CCDC 656592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H20 Cd2 N8 O7, H2 O' _chemical_formula_sum 'C37 H22 Cd2 N8 O8' _chemical_formula_weight 931.43 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.243(2) _cell_length_b 11.406(2) _cell_length_c 15.414(3) _cell_angle_alpha 74.56(3) _cell_angle_beta 70.73(3) _cell_angle_gamma 85.23(3) _cell_volume 1638.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13390 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.888 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.629 _exptl_absorpt_correction_T_max 0.721 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16143 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7368 _reflns_number_gt 5951 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO ' _computing_data_reduction 'PROCESS-AUTO ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0351P)^2^+1.1807P] 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 7368 _refine_ls_number_parameters 508 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0283(3) 0.8067(3) 0.1037(2) 0.0268(7) Uani 1 1 d . . . C2 C 0.8911(3) 0.8626(3) 0.1014(2) 0.0235(6) Uani 1 1 d . . . C3 C 0.7991(3) 0.8008(3) 0.0808(2) 0.0256(6) Uani 1 1 d . . . H3 H 0.8231 0.7257 0.0672 0.031 Uiso 1 1 calc R . . C4 C 0.6698(3) 0.8513(3) 0.0805(2) 0.0244(6) Uani 1 1 d . . . C5 C 0.5676(3) 0.7810(3) 0.0626(2) 0.0284(7) Uani 1 1 d . . . C6 C 0.6384(3) 0.9660(3) 0.0956(2) 0.0265(7) Uani 1 1 d . . . H6 H 0.5551 1.0020 0.0914 0.032 Uiso 1 1 calc R . . C7 C 0.7305(3) 1.0282(3) 0.1170(2) 0.0247(6) Uani 1 1 d . . . C8 C 0.6951(3) 1.1544(3) 0.1313(2) 0.0294(7) Uani 1 1 d . . . C9 C 0.8552(3) 0.9752(3) 0.1219(2) 0.0254(6) Uani 1 1 d . . . H9 H 0.9152 1.0147 0.1390 0.031 Uiso 1 1 calc R . . C10 C 0.5862(3) 0.7236(3) -0.2998(2) 0.0294(7) Uani 1 1 d . . . C11 C 0.6737(4) 0.8057(3) -0.2842(2) 0.0317(7) Uani 1 1 d . . . C12 C 0.7360(4) 0.9063(3) -0.3577(3) 0.0362(8) Uani 1 1 d . . . C13 C 0.8178(5) 0.9824(4) -0.3392(3) 0.0532(11) Uani 1 1 d . . . H13 H 0.8598 1.0509 -0.3859 0.064 Uiso 1 1 calc R . . C14 C 0.8358(6) 0.9558(4) -0.2522(3) 0.0690(16) Uani 1 1 d . . . H14 H 0.8918 1.0048 -0.2395 0.083 Uiso 1 1 calc R . . C15 C 0.7695(5) 0.8546(4) -0.1829(3) 0.0532(11) Uani 1 1 d . . . H15 H 0.7807 0.8382 -0.1234 0.064 Uiso 1 1 calc R . . C16 C 0.7111(4) 0.9298(3) -0.4481(3) 0.0405(9) Uani 1 1 d . . . C17 C 0.6255(4) 0.8525(4) -0.4624(3) 0.0418(9) Uani 1 1 d . . . C18 C 0.6577(5) 0.9699(4) -0.6115(3) 0.0602(13) Uani 1 1 d . . . H18 H 0.6416 0.9878 -0.6696 0.072 Uiso 1 1 calc R . . C19 C 0.7425(5) 1.0461(4) -0.5976(3) 0.0573(12) Uani 1 1 d . . . H17 H 0.7805 1.1136 -0.6469 0.069 Uiso 1 1 calc R . . C20 C 0.5624(4) 0.7464(3) -0.3855(3) 0.0381(8) Uani 1 1 d . . . C21 C 0.4784(5) 0.6653(5) -0.3968(3) 0.0632(14) Uani 1 1 d . . . H21 H 0.4614 0.6775 -0.4542 0.076 Uiso 1 1 calc R . . C22 C 0.4212(5) 0.5677(4) -0.3233(3) 0.0621(13) Uani 1 1 d . . . H22 H 0.3649 0.5132 -0.3301 0.075 Uiso 1 1 calc R . . C23 C 0.4481(4) 0.5512(3) -0.2388(3) 0.0376(8) Uani 1 1 d . . . H23 H 0.4080 0.4851 -0.1887 0.045 Uiso 1 1 calc R . . C24 C 0.3487(5) 0.7409(4) 0.2921(3) 0.0490(11) Uani 1 1 d . . . H24 H 0.3871 0.8103 0.2451 0.059 Uiso 1 1 calc R . . C25 C 0.3660(6) 0.7226(5) 0.3801(3) 0.0692(16) Uani 1 1 d . . . H25 H 0.4161 0.7778 0.3917 0.083 Uiso 1 1 calc R . . C26 C 0.2213(4) 0.5651(3) 0.3413(2) 0.0326(7) Uani 1 1 d . . . C27 C 0.1368(3) 0.4860(3) 0.3204(2) 0.0313(7) Uani 1 1 d . . . C28 C 0.0399(4) 0.4519(4) 0.2150(3) 0.0455(10) Uani 1 1 d . . . H28 H 0.0278 0.4750 0.1556 0.055 Uiso 1 1 calc R . . C29 C -0.0279(4) 0.3471(4) 0.2802(3) 0.0494(10) Uani 1 1 d . . . H29 H -0.0838 0.3017 0.2643 0.059 Uiso 1 1 calc R . . C30 C -0.0105(4) 0.3127(4) 0.3678(3) 0.0484(10) Uani 1 1 d . . . H30 H -0.0545 0.2432 0.4121 0.058 Uiso 1 1 calc R . . C31 C 0.0736(4) 0.3823(3) 0.3905(3) 0.0353(8) Uani 1 1 d . . . C32 C 0.0941(4) 0.3533(3) 0.4829(3) 0.0384(8) Uani 1 1 d . . . C33 C 0.1746(4) 0.4293(4) 0.5023(3) 0.0430(9) Uani 1 1 d . . . C34 C 0.1399(5) 0.3073(4) 0.6486(3) 0.0592(12) Uani 1 1 d . . . H34 H 0.1519 0.2880 0.7080 0.071 Uiso 1 1 calc R . . C35 C 0.0583(5) 0.2309(4) 0.6304(3) 0.0618(13) Uani 1 1 d . . . H35 H 0.0187 0.1628 0.6784 0.074 Uiso 1 1 calc R . . C36 C 0.2364(4) 0.5387(4) 0.4302(3) 0.0434(9) Uani 1 1 d . . . C37 C 0.3074(6) 0.6215(5) 0.4496(3) 0.0756(18) Uani 1 1 d . . . H37 H 0.3154 0.6083 0.5098 0.091 Uiso 1 1 calc R . . N1 N 0.5290(3) 0.6259(2) -0.2261(2) 0.0289(6) Uani 1 1 d . . . N2 N 0.6908(3) 0.7804(3) -0.1980(2) 0.0356(7) Uani 1 1 d . . . N3 N 0.5983(4) 0.8723(3) -0.5450(2) 0.0531(9) Uani 1 1 d . . . N4 N 0.7722(4) 1.0286(3) -0.5192(2) 0.0491(9) Uani 1 1 d . . . N5 N 0.1207(3) 0.5198(3) 0.2341(2) 0.0350(7) Uani 1 1 d . . . N6 N 0.2800(3) 0.6641(2) 0.2716(2) 0.0350(7) Uani 1 1 d . . . N7 N 0.0344(4) 0.2498(3) 0.5491(2) 0.0491(9) Uani 1 1 d . . . N8 N 0.1998(4) 0.4040(3) 0.5862(3) 0.0563(10) Uani 1 1 d . . . O1 O 0.6131(3) 0.6904(2) 0.02866(19) 0.0390(6) Uani 1 1 d . . . O2 O 0.4454(2) 0.8159(2) 0.08347(18) 0.0352(5) Uani 1 1 d . . . O7 O 0.6459(2) 0.45820(18) -0.04252(17) 0.0249(5) Uani 1 1 d . . . O3 O 1.0675(2) 0.7184(2) 0.06717(19) 0.0371(6) Uani 1 1 d . . . O1W O -0.1467(5) 0.4272(4) 0.0694(3) 0.0753(10) Uani 1 1 d D . . O4 O 1.0987(2) 0.8481(2) 0.14126(19) 0.0368(6) Uani 1 1 d . . . O5 O 0.7395(3) 1.1895(2) 0.1861(2) 0.0488(7) Uani 1 1 d . . . O6 O 0.6230(3) 1.2165(2) 0.0832(2) 0.0450(7) Uani 1 1 d . . . Cd1 Cd 0.26695(2) 0.692721(19) 0.111640(17) 0.02528(7) Uani 1 1 d . . . Cd2 Cd 0.53877(2) 0.634495(18) -0.078436(16) 0.02475(7) Uani 1 1 d . . . H7 H 0.699(4) 0.466(3) -0.022(3) 0.033(12) Uiso 1 1 d . . . HW11 H -0.081(5) 0.370(4) 0.079(4) 0.10(2) Uiso 1 1 d D . . HW12 H -0.230(4) 0.400(8) 0.112(7) 0.32(8) 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 C1 0.0200(15) 0.0288(16) 0.0296(16) -0.0022(13) -0.0099(13) 0.0018(12) C2 0.0196(15) 0.0243(15) 0.0262(15) -0.0040(12) -0.0094(12) 0.0026(11) C3 0.0238(15) 0.0226(15) 0.0317(16) -0.0067(13) -0.0115(13) 0.0035(11) C4 0.0247(15) 0.0216(15) 0.0280(16) -0.0019(12) -0.0128(13) -0.0017(11) C5 0.0298(17) 0.0279(16) 0.0271(16) 0.0000(13) -0.0125(13) -0.0061(13) C6 0.0199(15) 0.0276(16) 0.0307(16) -0.0049(13) -0.0094(13) 0.0041(12) C7 0.0273(16) 0.0206(14) 0.0247(15) -0.0037(12) -0.0089(12) 0.0035(11) C8 0.0317(17) 0.0210(15) 0.0342(18) -0.0040(13) -0.0123(14) 0.0047(12) C9 0.0260(16) 0.0236(15) 0.0299(16) -0.0042(13) -0.0149(13) -0.0010(11) C10 0.0288(17) 0.0256(16) 0.0311(17) -0.0036(13) -0.0084(14) -0.0015(12) C11 0.0336(18) 0.0270(17) 0.0333(18) -0.0033(14) -0.0119(14) -0.0028(13) C12 0.042(2) 0.0289(17) 0.0334(18) -0.0032(15) -0.0086(16) -0.0057(14) C13 0.069(3) 0.044(2) 0.044(2) 0.0004(19) -0.018(2) -0.028(2) C14 0.093(4) 0.061(3) 0.056(3) 0.004(2) -0.031(3) -0.050(3) C15 0.063(3) 0.064(3) 0.037(2) -0.0051(19) -0.019(2) -0.030(2) C16 0.049(2) 0.0296(18) 0.0357(19) 0.0053(15) -0.0137(17) -0.0065(15) C17 0.048(2) 0.045(2) 0.0300(19) 0.0004(16) -0.0160(17) -0.0072(17) C18 0.074(3) 0.066(3) 0.033(2) 0.004(2) -0.020(2) -0.006(2) C19 0.071(3) 0.049(3) 0.040(2) 0.0114(19) -0.017(2) -0.014(2) C20 0.039(2) 0.043(2) 0.0319(18) -0.0054(16) -0.0124(16) -0.0077(16) C21 0.076(3) 0.078(3) 0.043(2) -0.001(2) -0.031(2) -0.036(3) C22 0.073(3) 0.060(3) 0.059(3) -0.001(2) -0.031(2) -0.036(2) C23 0.041(2) 0.0317(18) 0.037(2) -0.0039(15) -0.0106(16) -0.0111(15) C24 0.070(3) 0.044(2) 0.036(2) -0.0060(17) -0.018(2) -0.024(2) C25 0.101(4) 0.068(3) 0.046(3) -0.001(2) -0.032(3) -0.048(3) C26 0.0314(18) 0.0322(18) 0.0314(18) -0.0081(14) -0.0065(14) -0.0002(13) C27 0.0273(17) 0.0315(17) 0.0296(17) -0.0055(14) -0.0038(14) -0.0007(13) C28 0.049(2) 0.048(2) 0.042(2) -0.0068(18) -0.0178(18) -0.0135(18) C29 0.046(2) 0.052(2) 0.051(2) -0.015(2) -0.0113(19) -0.0185(19) C30 0.043(2) 0.042(2) 0.051(2) 0.0003(18) -0.0083(19) -0.0164(17) C31 0.0295(18) 0.0347(18) 0.0375(19) -0.0061(15) -0.0066(15) -0.0046(14) C32 0.038(2) 0.0328(19) 0.0348(19) -0.0022(16) -0.0035(16) -0.0026(15) C33 0.046(2) 0.045(2) 0.0317(19) -0.0036(16) -0.0086(17) -0.0018(17) C34 0.067(3) 0.066(3) 0.038(2) 0.003(2) -0.020(2) -0.008(2) C35 0.067(3) 0.054(3) 0.047(3) 0.015(2) -0.013(2) -0.017(2) C36 0.055(2) 0.042(2) 0.0325(19) -0.0003(16) -0.0163(18) -0.0142(18) C37 0.114(5) 0.080(4) 0.043(3) 0.004(2) -0.041(3) -0.050(3) N1 0.0308(15) 0.0255(14) 0.0285(14) -0.0049(11) -0.0081(12) -0.0017(11) N2 0.0390(17) 0.0347(16) 0.0328(16) -0.0013(13) -0.0141(13) -0.0111(12) N3 0.061(2) 0.059(2) 0.0374(18) 0.0011(16) -0.0214(17) -0.0122(18) N4 0.060(2) 0.0417(19) 0.0376(18) 0.0018(15) -0.0114(16) -0.0126(16) N5 0.0372(17) 0.0343(15) 0.0324(15) -0.0065(13) -0.0095(13) -0.0061(12) N6 0.0436(18) 0.0277(15) 0.0328(16) -0.0029(12) -0.0132(13) -0.0064(12) N7 0.045(2) 0.049(2) 0.0420(19) -0.0004(16) -0.0076(16) -0.0072(15) N8 0.066(3) 0.060(2) 0.0388(19) -0.0026(17) -0.0161(18) -0.0122(19) O1 0.0449(15) 0.0319(13) 0.0535(16) -0.0179(12) -0.0285(13) 0.0044(10) O2 0.0254(12) 0.0417(14) 0.0403(14) -0.0093(11) -0.0122(10) -0.0061(10) O7 0.0214(11) 0.0208(11) 0.0324(12) -0.0055(9) -0.0099(10) 0.0013(8) O3 0.0298(13) 0.0394(13) 0.0487(15) -0.0192(12) -0.0185(11) 0.0150(10) O1W 0.081(3) 0.076(3) 0.082(3) -0.032(2) -0.031(2) -0.010(2) O4 0.0271(12) 0.0403(13) 0.0507(16) -0.0152(12) -0.0212(11) 0.0065(10) O5 0.078(2) 0.0362(14) 0.0502(17) -0.0208(13) -0.0403(16) 0.0153(13) O6 0.0545(17) 0.0312(13) 0.0627(18) -0.0151(12) -0.0381(15) 0.0188(11) Cd1 0.01912(12) 0.02584(13) 0.03405(14) -0.01095(10) -0.01087(9) 0.00370(8) Cd2 0.02679(13) 0.01854(12) 0.02601(12) -0.00242(9) -0.00731(9) 0.00060(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O4 1.248(4) . ? C1 O3 1.257(4) . ? C1 C2 1.501(4) . ? C1 Cd1 2.696(3) 1_655 ? C2 C3 1.382(4) . ? C2 C9 1.395(4) . ? C3 C4 1.401(4) . ? C3 H3 0.9300 . ? C4 C6 1.382(4) . ? C4 C5 1.505(4) . ? C5 O2 1.245(4) . ? C5 O1 1.267(4) . ? C6 C7 1.394(4) . ? C6 H6 0.9300 . ? C7 C9 1.384(4) . ? C7 C8 1.511(4) . ? C8 O5 1.243(4) . ? C8 O6 1.262(4) . ? C9 H9 0.9300 . ? C10 N1 1.368(4) . ? C10 C20 1.376(5) . ? C10 C11 1.462(5) . ? C11 N2 1.350(5) . ? C11 C12 1.399(5) . ? C12 C13 1.397(5) . ? C12 C16 1.450(5) . ? C13 C14 1.364(6) . ? C13 H13 0.9300 . ? C14 C15 1.390(6) . ? C14 H14 0.9300 . ? C15 N2 1.328(5) . ? C15 H15 0.9300 . ? C16 N4 1.367(4) . ? C16 C17 1.399(5) . ? C17 N3 1.348(5) . ? C17 C20 1.465(5) . ? C18 N3 1.325(5) . ? C18 C19 1.378(6) . ? C18 H18 0.9300 . ? C19 N4 1.304(6) . ? C19 H17 0.9300 . ? C20 C21 1.394(5) . ? C21 C22 1.365(6) . ? C21 H21 0.9300 . ? C22 C23 1.381(6) . ? C22 H22 0.9300 . ? C23 N1 1.327(4) . ? C23 H23 0.9300 . ? C24 N6 1.326(5) . ? C24 C25 1.385(6) . ? C24 H24 0.9300 . ? C25 C37 1.368(6) . ? C25 H25 0.9300 . ? C26 N6 1.354(4) . ? C26 C36 1.381(5) . ? C26 C27 1.460(5) . ? C27 N5 1.344(5) . ? C27 C31 1.404(5) . ? C28 N5 1.327(5) . ? C28 C29 1.400(5) . ? C28 H28 0.9300 . ? C29 C30 1.370(6) . ? C29 H29 0.9300 . ? C30 C31 1.397(5) . ? C30 H30 0.9300 . ? C31 C32 1.455(5) . ? C32 N7 1.370(4) . ? C32 C33 1.392(6) . ? C33 N8 1.354(5) . ? C33 C36 1.457(5) . ? C34 N8 1.294(5) . ? C34 C35 1.394(7) . ? C34 H34 0.9300 . ? C35 N7 1.314(6) . ? C35 H35 0.9300 . ? C36 C37 1.385(6) . ? C37 H37 0.9300 . ? N1 Cd2 2.340(3) . ? N2 Cd2 2.344(3) . ? N5 Cd1 2.518(3) . ? N6 Cd1 2.447(3) . ? O1 Cd2 2.277(3) . ? O2 Cd1 2.254(2) . ? O7 Cd1 2.233(2) 2_665 ? O7 Cd2 2.235(2) . ? O7 Cd2 2.265(2) 2_665 ? O7 H7 0.73(4) . ? O3 Cd1 2.334(2) 1_655 ? O1W HW11 0.92(2) . ? O1W HW12 0.91(2) . ? O4 Cd1 2.393(2) 1_655 ? O6 Cd2 2.277(3) 2_675 ? Cd1 O7 2.233(2) 2_665 ? Cd1 O3 2.334(2) 1_455 ? Cd1 O4 2.393(2) 1_455 ? Cd1 C1 2.696(3) 1_455 ? Cd2 O7 2.265(2) 2_665 ? Cd2 O6 2.277(3) 2_675 ? Cd2 Cd2 3.3284(14) 2_665 ? 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 O4 C1 O3 122.4(3) . . ? O4 C1 C2 119.9(3) . . ? O3 C1 C2 117.7(3) . . ? O4 C1 Cd1 62.56(17) . 1_655 ? O3 C1 Cd1 59.89(17) . 1_655 ? C2 C1 Cd1 176.4(2) . 1_655 ? C3 C2 C9 120.0(3) . . ? C3 C2 C1 119.8(3) . . ? C9 C2 C1 120.2(3) . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C6 C4 C3 119.4(3) . . ? C6 C4 C5 120.8(3) . . ? C3 C4 C5 119.8(3) . . ? O2 C5 O1 125.6(3) . . ? O2 C5 C4 117.2(3) . . ? O1 C5 C4 117.1(3) . . ? C4 C6 C7 120.6(3) . . ? C4 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C9 C7 C6 119.6(3) . . ? C9 C7 C8 120.7(3) . . ? C6 C7 C8 119.6(3) . . ? O5 C8 O6 125.6(3) . . ? O5 C8 C7 119.3(3) . . ? O6 C8 C7 115.1(3) . . ? C7 C9 C2 120.1(3) . . ? C7 C9 H9 120.0 . . ? C2 C9 H9 120.0 . . ? N1 C10 C20 122.2(3) . . ? N1 C10 C11 117.6(3) . . ? C20 C10 C11 120.2(3) . . ? N2 C11 C12 122.5(3) . . ? N2 C11 C10 117.7(3) . . ? C12 C11 C10 119.8(3) . . ? C13 C12 C11 117.6(4) . . ? C13 C12 C16 122.5(3) . . ? C11 C12 C16 119.8(3) . . ? C14 C13 C12 119.6(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 119.1(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N2 C15 C14 122.8(4) . . ? N2 C15 H15 118.6 . . ? C14 C15 H15 118.6 . . ? N4 C16 C17 120.4(4) . . ? N4 C16 C12 119.3(3) . . ? C17 C16 C12 120.4(3) . . ? N3 C17 C16 122.2(3) . . ? N3 C17 C20 118.5(4) . . ? C16 C17 C20 119.4(3) . . ? N3 C18 C19 122.3(4) . . ? N3 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? N4 C19 C18 123.5(4) . . ? N4 C19 H17 118.2 . . ? C18 C19 H17 118.2 . . ? C10 C20 C21 118.0(3) . . ? C10 C20 C17 120.4(3) . . ? C21 C20 C17 121.6(4) . . ? C22 C21 C20 119.9(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 119.1(4) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? N1 C23 C22 122.6(3) . . ? N1 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? N6 C24 C25 123.1(4) . . ? N6 C24 H24 118.4 . . ? C25 C24 H24 118.4 . . ? C37 C25 C24 118.3(4) . . ? C37 C25 H25 120.8 . . ? C24 C25 H25 120.8 . . ? N6 C26 C36 122.5(3) . . ? N6 C26 C27 117.6(3) . . ? C36 C26 C27 119.9(3) . . ? N5 C27 C31 123.3(3) . . ? N5 C27 C26 117.0(3) . . ? C31 C27 C26 119.7(3) . . ? N5 C28 C29 123.0(4) . . ? N5 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? C30 C29 C28 118.8(4) . . ? C30 C29 H29 120.6 . . ? C28 C29 H29 120.6 . . ? C29 C30 C31 119.8(4) . . ? C29 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C30 C31 C27 117.2(4) . . ? C30 C31 C32 122.9(3) . . ? C27 C31 C32 119.9(3) . . ? N7 C32 C33 121.2(4) . . ? N7 C32 C31 118.7(4) . . ? C33 C32 C31 120.1(3) . . ? N8 C33 C32 122.1(4) . . ? N8 C33 C36 118.1(4) . . ? C32 C33 C36 119.7(4) . . ? N8 C34 C35 122.8(4) . . ? N8 C34 H34 118.6 . . ? C35 C34 H34 118.6 . . ? N7 C35 C34 123.6(4) . . ? N7 C35 H35 118.2 . . ? C34 C35 H35 118.2 . . ? C37 C36 C26 118.0(4) . . ? C37 C36 C33 121.3(4) . . ? C26 C36 C33 120.6(4) . . ? C25 C37 C36 120.0(4) . . ? C25 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C23 N1 C10 118.3(3) . . ? C23 N1 Cd2 124.8(2) . . ? C10 N1 Cd2 115.0(2) . . ? C15 N2 C11 118.2(3) . . ? C15 N2 Cd2 124.7(3) . . ? C11 N2 Cd2 115.5(2) . . ? C18 N3 C17 115.6(4) . . ? C19 N4 C16 116.0(4) . . ? C28 N5 C27 118.0(3) . . ? C28 N5 Cd1 123.4(3) . . ? C27 N5 Cd1 118.2(2) . . ? C24 N6 C26 118.0(3) . . ? C24 N6 Cd1 121.8(2) . . ? C26 N6 Cd1 120.1(2) . . ? C35 N7 C32 114.5(4) . . ? C34 N8 C33 115.7(4) . . ? C5 O1 Cd2 124.4(2) . . ? C5 O2 Cd1 122.5(2) . . ? Cd1 O7 Cd2 136.79(12) 2_665 . ? Cd1 O7 Cd2 101.44(9) 2_665 2_665 ? Cd2 O7 Cd2 95.40(9) . 2_665 ? Cd1 O7 H7 102(3) 2_665 . ? Cd2 O7 H7 110(3) . . ? Cd2 O7 H7 108(3) 2_665 . ? C1 O3 Cd1 92.3(2) . 1_655 ? HW11 O1W HW12 108(3) . . ? C1 O4 Cd1 89.87(19) . 1_655 ? C8 O6 Cd2 145.1(3) . 2_675 ? O7 Cd1 O2 106.77(9) 2_665 . ? O7 Cd1 O3 95.89(9) 2_665 1_455 ? O2 Cd1 O3 133.63(9) . 1_455 ? O7 Cd1 O4 150.91(9) 2_665 1_455 ? O2 Cd1 O4 93.19(9) . 1_455 ? O3 Cd1 O4 55.32(8) 1_455 1_455 ? O7 Cd1 N6 115.45(10) 2_665 . ? O2 Cd1 N6 78.39(10) . . ? O3 Cd1 N6 127.06(10) 1_455 . ? O4 Cd1 N6 88.77(10) 1_455 . ? O7 Cd1 N5 80.87(9) 2_665 . ? O2 Cd1 N5 142.72(10) . . ? O3 Cd1 N5 79.60(10) 1_455 . ? O4 Cd1 N5 96.10(10) 1_455 . ? N6 Cd1 N5 65.84(10) . . ? O7 Cd1 C1 123.61(10) 2_665 1_455 ? O2 Cd1 C1 115.28(9) . 1_455 ? O3 Cd1 C1 27.76(9) 1_455 1_455 ? O4 Cd1 C1 27.57(9) 1_455 1_455 ? N6 Cd1 C1 108.59(11) . 1_455 ? N5 Cd1 C1 86.96(10) . 1_455 ? O7 Cd2 O7 84.60(9) . 2_665 ? O7 Cd2 O6 163.67(10) . 2_675 ? O7 Cd2 O6 79.15(10) 2_665 2_675 ? O7 Cd2 O1 86.11(9) . . ? O7 Cd2 O1 89.06(10) 2_665 . ? O6 Cd2 O1 95.16(10) 2_675 . ? O7 Cd2 N1 98.84(10) . . ? O7 Cd2 N1 111.88(10) 2_665 . ? O6 Cd2 N1 85.85(10) 2_675 . ? O1 Cd2 N1 158.78(10) . . ? O7 Cd2 N2 111.45(10) . . ? O7 Cd2 N2 163.40(10) 2_665 . ? O6 Cd2 N2 84.87(11) 2_675 . ? O1 Cd2 N2 87.90(10) . . ? N1 Cd2 N2 71.06(10) . . ? O7 Cd2 Cd2 42.64(6) . 2_665 ? O7 Cd2 Cd2 41.96(6) 2_665 2_665 ? O6 Cd2 Cd2 121.09(8) 2_675 2_665 ? O1 Cd2 Cd2 86.75(7) . 2_665 ? N1 Cd2 Cd2 110.90(7) . 2_665 ? N2 Cd2 Cd2 153.85(8) . 2_665 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.875 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.102 # Attachment 'compound-4.cif' data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 656593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H12 Cu2 N4 O7' _chemical_formula_sum 'C23 H12 Cu2 N4 O7' _chemical_formula_weight 583.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 9.4403(19) _cell_length_b 14.647(3) _cell_length_c 15.286(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.39(3) _cell_angle_gamma 90.00 _cell_volume 2072.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16915 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 2.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.537 _exptl_absorpt_correction_T_max 0.699 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 19897 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4715 _reflns_number_gt 4109 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO ' _computing_data_reduction 'PROCESS-AUTO ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0487P)^2^+0.4460P] 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 4715 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 C1 C 0.9984(3) 0.6568(2) -0.0895(2) 0.0421(7) Uani 1 1 d . . . H1 H 0.9142 0.6846 -0.0800 0.051 Uiso 1 1 calc R . . C2 C 0.9878(3) 0.5859(3) -0.1510(3) 0.0566(10) Uani 1 1 d . . . H2 H 0.8978 0.5671 -0.1822 0.068 Uiso 1 1 calc R . . C3 C 1.1108(3) 0.5439(2) -0.1652(2) 0.0489(8) Uani 1 1 d . . . H3 H 1.1051 0.4956 -0.2052 0.059 Uiso 1 1 calc R . . C4 C 1.2460(3) 0.57465(17) -0.11876(18) 0.0305(5) Uani 1 1 d . . . C5 C 1.2469(3) 0.64664(16) -0.05904(16) 0.0249(5) Uani 1 1 d . . . C6 C 1.3826(3) 0.68398(15) -0.01041(16) 0.0235(5) Uani 1 1 d . . . C7 C 1.4947(3) 0.78832(17) 0.09217(19) 0.0329(6) Uani 1 1 d . . . H7 H 1.4890 0.8357 0.1318 0.040 Uiso 1 1 calc R . . C8 C 1.6306(3) 0.7570(2) 0.0840(2) 0.0390(6) Uani 1 1 d . . . H8 H 1.7136 0.7831 0.1176 0.047 Uiso 1 1 calc R . . C9 C 1.6407(3) 0.68726(19) 0.02590(19) 0.0363(6) Uani 1 1 d . . . H9 H 1.7306 0.6661 0.0189 0.044 Uiso 1 1 calc R . . C10 C 1.5140(3) 0.64820(17) -0.02290(16) 0.0271(5) Uani 1 1 d . . . C11 C 1.5134(3) 0.57144(17) -0.08365(17) 0.0297(5) Uani 1 1 d . . . C12 C 1.3828(3) 0.53536(18) -0.13015(16) 0.0296(5) Uani 1 1 d . . . C13 C 1.6351(3) 0.4646(2) -0.1468(2) 0.0424(7) Uani 1 1 d . . . H13 H 1.7211 0.4374 -0.1542 0.051 Uiso 1 1 calc R . . C14 C 1.5062(3) 0.4290(2) -0.19355(19) 0.0395(7) Uani 1 1 d . . . H14 H 1.5086 0.3797 -0.2316 0.047 Uiso 1 1 calc R . . C15 C 0.7457(2) 1.07419(15) 0.11842(15) 0.0214(4) Uani 1 1 d . . . C16 C 0.6020(2) 1.10036(15) 0.14000(14) 0.0186(4) Uani 1 1 d . . . C17 C 0.4841(2) 1.04296(15) 0.11478(14) 0.0190(4) Uani 1 1 d . . . H17 H 0.4924 0.9917 0.0803 0.023 Uiso 1 1 calc R . . C18 C 0.3534(2) 1.06123(14) 0.14047(15) 0.0191(4) Uani 1 1 d . . . C19 C 0.2327(2) 0.99384(15) 0.11735(14) 0.0186(4) Uani 1 1 d . . . C20 C 0.3419(2) 1.13740(15) 0.19289(15) 0.0211(4) Uani 1 1 d . . . H20 H 0.2551 1.1498 0.2105 0.025 Uiso 1 1 calc R . . C21 C 0.4601(2) 1.19543(14) 0.21927(15) 0.0199(4) Uani 1 1 d . . . C22 C 0.4491(2) 1.26995(16) 0.28560(16) 0.0255(5) Uani 1 1 d . . . C23 C 0.5885(2) 1.17788(15) 0.19062(15) 0.0199(4) Uani 1 1 d . . . H23 H 0.6657 1.2181 0.2053 0.024 Uiso 1 1 calc R . . N1 N 1.1248(2) 0.68635(14) -0.04378(14) 0.0276(4) Uani 1 1 d . . . N2 N 1.3726(2) 0.75351(13) 0.04583(13) 0.0251(4) Uani 1 1 d . . . N3 N 1.3794(3) 0.46333(16) -0.18543(15) 0.0356(5) Uani 1 1 d . . . N4 N 1.6421(2) 0.53531(18) -0.09224(16) 0.0381(5) Uani 1 1 d . . . O1 O 0.83363(18) 1.13434(12) 0.11059(12) 0.0303(4) Uani 1 1 d . . . O2 O 0.76387(17) 0.98820(11) 0.11061(12) 0.0267(4) Uani 1 1 d . . . O3 O 0.26151(18) 0.92131(11) 0.08254(13) 0.0307(4) Uani 1 1 d . . . O4 O 0.11153(17) 1.01429(11) 0.13552(12) 0.0263(4) Uani 1 1 d . . . O5 O 0.53902(19) 1.33514(12) 0.29122(12) 0.0293(4) Uani 1 1 d . . . O6 O 0.3551(2) 1.25993(16) 0.33205(15) 0.0493(6) Uani 1 1 d . . . O7 O 0.96099(19) 0.84909(12) 0.01265(13) 0.0267(4) Uani 1 1 d . . . Cu1 Cu 1.15964(3) 0.803813(18) 0.035625(19) 0.02104(9) Uani 1 1 d . . . Cu2 Cu 0.94598(3) 0.927787(17) 0.111582(17) 0.01754(9) Uani 1 1 d . . . H7A H 0.954(4) 0.873(3) -0.028(2) 0.048(11) Uiso 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 C1 0.0251(13) 0.0480(17) 0.0539(17) -0.0152(14) 0.0094(13) -0.0026(12) C2 0.0300(15) 0.065(2) 0.071(2) -0.0331(19) 0.0024(15) -0.0103(15) C3 0.0385(16) 0.0518(19) 0.0549(19) -0.0268(16) 0.0053(14) -0.0036(14) C4 0.0312(13) 0.0297(13) 0.0313(13) -0.0040(10) 0.0076(11) 0.0006(10) C5 0.0261(11) 0.0230(11) 0.0267(11) 0.0021(9) 0.0081(10) 0.0010(9) C6 0.0250(11) 0.0203(11) 0.0265(11) 0.0031(9) 0.0080(9) 0.0015(9) C7 0.0311(13) 0.0242(12) 0.0414(14) -0.0021(11) 0.0021(11) -0.0024(10) C8 0.0259(12) 0.0359(15) 0.0524(17) -0.0058(13) 0.0010(12) -0.0060(11) C9 0.0228(12) 0.0383(15) 0.0488(16) 0.0006(12) 0.0092(12) 0.0022(11) C10 0.0260(12) 0.0265(12) 0.0303(12) 0.0033(10) 0.0092(10) 0.0018(9) C11 0.0309(13) 0.0321(13) 0.0291(12) 0.0043(10) 0.0130(11) 0.0077(10) C12 0.0344(13) 0.0297(13) 0.0267(11) 0.0005(10) 0.0108(10) 0.0065(11) C13 0.0458(16) 0.0448(17) 0.0421(15) -0.0001(13) 0.0216(13) 0.0141(14) C14 0.0523(17) 0.0372(15) 0.0321(14) -0.0041(11) 0.0157(13) 0.0095(13) C15 0.0176(10) 0.0229(11) 0.0244(11) -0.0009(9) 0.0062(9) 0.0010(8) C16 0.0172(10) 0.0174(10) 0.0221(10) 0.0018(8) 0.0064(8) 0.0012(8) C17 0.0185(10) 0.0168(10) 0.0225(10) -0.0026(8) 0.0060(9) 0.0012(8) C18 0.0149(9) 0.0176(10) 0.0256(11) 0.0013(8) 0.0058(8) 0.0000(8) C19 0.0187(10) 0.0182(10) 0.0182(10) 0.0004(8) 0.0021(8) -0.0007(8) C20 0.0167(10) 0.0201(10) 0.0282(11) -0.0024(9) 0.0087(9) 0.0003(8) C21 0.0201(10) 0.0184(10) 0.0219(10) -0.0024(8) 0.0060(9) -0.0009(8) C22 0.0203(11) 0.0241(11) 0.0324(12) -0.0088(10) 0.0056(10) -0.0009(9) C23 0.0163(10) 0.0178(10) 0.0261(11) -0.0013(8) 0.0052(9) -0.0027(8) N1 0.0254(10) 0.0253(10) 0.0331(11) -0.0019(8) 0.0085(9) -0.0005(8) N2 0.0246(10) 0.0206(9) 0.0295(10) 0.0005(8) 0.0041(8) 0.0003(8) N3 0.0447(13) 0.0322(12) 0.0311(11) -0.0049(9) 0.0102(10) 0.0057(10) N4 0.0321(12) 0.0429(13) 0.0428(13) -0.0012(11) 0.0156(10) 0.0091(10) O1 0.0211(8) 0.0275(9) 0.0456(10) -0.0019(8) 0.0147(8) -0.0048(7) O2 0.0174(7) 0.0212(8) 0.0427(10) -0.0021(7) 0.0085(7) 0.0041(6) O3 0.0217(8) 0.0219(8) 0.0506(11) -0.0132(8) 0.0116(8) -0.0037(6) O4 0.0166(7) 0.0235(8) 0.0412(10) -0.0076(7) 0.0114(7) -0.0023(6) O5 0.0329(9) 0.0214(8) 0.0349(9) -0.0092(7) 0.0096(8) -0.0061(7) O6 0.0387(11) 0.0601(14) 0.0585(13) -0.0375(11) 0.0321(10) -0.0214(10) O7 0.0254(9) 0.0271(9) 0.0278(9) -0.0005(8) 0.0060(7) 0.0024(7) Cu1 0.01875(15) 0.01638(14) 0.02929(16) -0.00401(10) 0.00794(11) 0.00083(10) Cu2 0.01312(14) 0.01516(14) 0.02573(15) 0.00088(10) 0.00721(10) 0.00112(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.330(3) . ? C1 C2 1.392(4) . ? C1 H1 0.9300 . ? C2 C3 1.369(4) . ? C2 H2 0.9300 . ? C3 C4 1.406(4) . ? C3 H3 0.9300 . ? C4 C5 1.394(3) . ? C4 C12 1.455(4) . ? C5 N1 1.352(3) . ? C5 C6 1.455(3) . ? C6 N2 1.348(3) . ? C6 C10 1.394(3) . ? C7 N2 1.330(3) . ? C7 C8 1.391(4) . ? C7 H7 0.9300 . ? C8 C9 1.369(4) . ? C8 H8 0.9300 . ? C9 C10 1.401(4) . ? C9 H9 0.9300 . ? C10 C11 1.457(4) . ? C11 N4 1.356(3) . ? C11 C12 1.400(4) . ? C12 N3 1.348(3) . ? C13 N4 1.324(4) . ? C13 C14 1.386(5) . ? C13 H13 0.9300 . ? C14 N3 1.327(4) . ? C14 H14 0.9300 . ? C15 O1 1.232(3) . ? C15 O2 1.280(3) . ? C15 C16 1.508(3) . ? C16 C17 1.388(3) . ? C16 C23 1.394(3) . ? C17 C18 1.393(3) . ? C17 H17 0.9300 . ? C18 C20 1.390(3) . ? C18 C19 1.496(3) . ? C19 O3 1.242(3) . ? C19 O4 1.265(3) . ? C20 C21 1.397(3) . ? C20 H20 0.9300 . ? C21 C23 1.392(3) . ? C21 C22 1.507(3) . ? C22 O6 1.250(3) . ? C22 O5 1.269(3) . ? C23 H23 0.9300 . ? N1 Cu1 2.094(2) . ? N2 Cu1 2.118(2) . ? O1 Cu1 2.4241(19) 3_775 ? O2 Cu2 1.9310(16) . ? O3 Cu1 2.0319(17) 1_455 ? O4 Cu2 1.9889(16) 1_455 ? O5 Cu2 1.9964(17) 2_655 ? O6 Cu1 2.153(2) 2_655 ? O7 Cu2 1.9287(18) . ? O7 Cu1 1.9544(18) . ? O7 H7A 0.70(4) . ? Cu1 O3 2.0319(17) 1_655 ? Cu1 O6 2.153(2) 2_645 ? Cu1 O1 2.4241(19) 3_775 ? Cu2 O4 1.9889(16) 1_655 ? Cu2 O5 1.9964(17) 2_645 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.3(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 117.4(2) . . ? C5 C4 C12 119.1(2) . . ? C3 C4 C12 123.4(2) . . ? N1 C5 C4 122.9(2) . . ? N1 C5 C6 116.4(2) . . ? C4 C5 C6 120.7(2) . . ? N2 C6 C10 123.2(2) . . ? N2 C6 C5 116.4(2) . . ? C10 C6 C5 120.4(2) . . ? N2 C7 C8 122.9(3) . . ? N2 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.3(2) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C6 C10 C9 117.6(2) . . ? C6 C10 C11 119.1(2) . . ? C9 C10 C11 123.4(2) . . ? N4 C11 C12 121.3(2) . . ? N4 C11 C10 118.2(2) . . ? C12 C11 C10 120.5(2) . . ? N3 C12 C11 121.6(2) . . ? N3 C12 C4 118.2(2) . . ? C11 C12 C4 120.2(2) . . ? N4 C13 C14 123.3(3) . . ? N4 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? N3 C14 C13 121.7(3) . . ? N3 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? O1 C15 O2 126.1(2) . . ? O1 C15 C16 119.5(2) . . ? O2 C15 C16 114.43(19) . . ? C17 C16 C23 119.4(2) . . ? C17 C16 C15 119.49(19) . . ? C23 C16 C15 120.91(19) . . ? C16 C17 C18 120.8(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C20 C18 C17 119.4(2) . . ? C20 C18 C19 121.5(2) . . ? C17 C18 C19 118.85(19) . . ? O3 C19 O4 125.5(2) . . ? O3 C19 C18 116.4(2) . . ? O4 C19 C18 118.13(19) . . ? C18 C20 C21 120.4(2) . . ? C18 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C23 C21 C20 119.5(2) . . ? C23 C21 C22 121.7(2) . . ? C20 C21 C22 118.6(2) . . ? O6 C22 O5 126.2(2) . . ? O6 C22 C21 116.6(2) . . ? O5 C22 C21 117.2(2) . . ? C21 C23 C16 120.4(2) . . ? C21 C23 H23 119.8 . . ? C16 C23 H23 119.8 . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Cu1 126.40(19) . . ? C5 N1 Cu1 114.33(16) . . ? C7 N2 C6 117.8(2) . . ? C7 N2 Cu1 128.05(17) . . ? C6 N2 Cu1 113.64(15) . . ? C14 N3 C12 116.4(2) . . ? C13 N4 C11 115.6(2) . . ? C15 O1 Cu1 119.83(16) . 3_775 ? C15 O2 Cu2 125.85(15) . . ? C19 O3 Cu1 138.33(16) . 1_455 ? C19 O4 Cu2 121.36(14) . 1_455 ? C22 O5 Cu2 120.67(16) . 2_655 ? C22 O6 Cu1 133.14(17) . 2_655 ? Cu2 O7 Cu1 106.16(9) . . ? Cu2 O7 H7A 113(3) . . ? Cu1 O7 H7A 104(3) . . ? O7 Cu1 O3 98.42(7) . 1_655 ? O7 Cu1 N1 98.01(8) . . ? O3 Cu1 N1 155.48(8) 1_655 . ? O7 Cu1 N2 173.99(8) . . ? O3 Cu1 N2 83.82(7) 1_655 . ? N1 Cu1 N2 78.17(8) . . ? O7 Cu1 O6 91.84(8) . 2_645 ? O3 Cu1 O6 92.02(9) 1_655 2_645 ? N1 Cu1 O6 105.51(9) . 2_645 ? N2 Cu1 O6 93.65(8) . 2_645 ? O7 Cu1 O1 84.64(7) . 3_775 ? O3 Cu1 O1 84.96(7) 1_655 3_775 ? N1 Cu1 O1 78.60(7) . 3_775 ? N2 Cu1 O1 90.03(7) . 3_775 ? O6 Cu1 O1 174.97(7) 2_645 3_775 ? O7 Cu2 O2 118.10(8) . . ? O7 Cu2 O4 110.38(8) . 1_655 ? O2 Cu2 O4 112.06(7) . 1_655 ? O7 Cu2 O5 99.90(8) . 2_645 ? O2 Cu2 O5 104.44(8) . 2_645 ? O4 Cu2 O5 111.00(8) 1_655 2_645 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.478 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.102 # Attachment 'compound-5.cif' data_compound-5 _database_code_depnum_ccdc_archive 'CCDC 656594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H12 N4 O7 Zn2' _chemical_formula_sum 'C23 H12 N4 O7 Zn2' _chemical_formula_weight 587.11 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 9.4496(19) _cell_length_b 14.686(3) _cell_length_c 15.217(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.15(3) _cell_angle_gamma 90.00 _cell_volume 2071.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16466 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.882 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 2.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.440 _exptl_absorpt_correction_T_max 0.528 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 20035 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4723 _reflns_number_gt 4026 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO ' _computing_data_reduction 'PROCESS-AUTO ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (Sheldrick, 1990)' _computing_publication_material SHELXL-97 _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^)+(0.0296P)^2^+1.6259P] 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 4723 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 C1 C 0.2445(2) -0.07542(15) 0.11732(13) 0.0187(4) Uani 1 1 d . . . C2 C 0.1015(2) -0.10147(14) 0.13994(14) 0.0172(4) Uani 1 1 d . . . C3 C 0.0882(2) -0.17862(14) 0.19093(14) 0.0185(4) Uani 1 1 d . . . H3 H 0.1650 -0.2190 0.2052 0.022 Uiso 1 1 calc R . . C4 C -0.0400(2) -0.19545(14) 0.22070(14) 0.0185(4) Uani 1 1 d . . . C5 C -0.0501(2) -0.26966(15) 0.28796(14) 0.0210(4) Uani 1 1 d . . . C6 C -0.1575(2) -0.13771(14) 0.19445(14) 0.0193(4) Uani 1 1 d . . . H6 H -0.2442 -0.1500 0.2124 0.023 Uiso 1 1 calc R . . C7 C -0.1460(2) -0.06191(14) 0.14163(13) 0.0171(4) Uani 1 1 d . . . C8 C -0.0158(2) -0.04377(14) 0.11544(13) 0.0174(4) Uani 1 1 d . . . H8 H -0.0073 0.0076 0.0811 0.021 Uiso 1 1 calc R . . C9 C -0.2668(2) 0.00559(14) 0.11850(13) 0.0174(4) Uani 1 1 d . . . C10 C 0.9964(3) 0.21144(17) 0.08890(17) 0.0316(5) Uani 1 1 d . . . H10 H 0.9913 0.1637 0.1283 0.038 Uiso 1 1 calc R . . C11 C 1.1314(3) 0.24252(18) 0.07955(19) 0.0375(6) Uani 1 1 d . . . H11 H 1.2145 0.2157 0.1119 0.045 Uiso 1 1 calc R . . C12 C 1.1409(3) 0.31305(18) 0.02231(18) 0.0351(6) Uani 1 1 d . . . H12 H 1.2306 0.3343 0.0150 0.042 Uiso 1 1 calc R . . C13 C 1.0143(3) 0.35293(16) -0.02526(15) 0.0258(5) Uani 1 1 d . . . C14 C 0.8830(3) 0.31717(15) -0.01209(15) 0.0224(4) Uani 1 1 d . . . C15 C 0.7473(3) 0.35479(15) -0.05973(15) 0.0235(5) Uani 1 1 d . . . C16 C 0.4997(3) 0.3463(2) -0.0891(2) 0.0397(6) Uani 1 1 d . . . H16 H 0.4154 0.3186 -0.0796 0.048 Uiso 1 1 calc R . . C17 C 0.4892(3) 0.4181(2) -0.1498(2) 0.0559(9) Uani 1 1 d . . . H17 H 0.3995 0.4377 -0.1804 0.067 Uiso 1 1 calc R . . C18 C 0.6125(3) 0.4595(2) -0.1638(2) 0.0473(8) Uani 1 1 d . . . H18 H 0.6073 0.5084 -0.2032 0.057 Uiso 1 1 calc R . . C19 C 0.7463(3) 0.42790(17) -0.11881(16) 0.0288(5) Uani 1 1 d . . . C20 C 0.8828(3) 0.46698(16) -0.13040(15) 0.0276(5) Uani 1 1 d . . . C21 C 1.0133(3) 0.43030(16) -0.08514(15) 0.0274(5) Uani 1 1 d . . . C22 C 1.0057(3) 0.57387(18) -0.19310(17) 0.0365(6) Uani 1 1 d . . . H22 H 1.0081 0.6236 -0.2306 0.044 Uiso 1 1 calc R . . C23 C 1.1348(3) 0.5378(2) -0.14727(18) 0.0394(6) Uani 1 1 d . . . H23 H 1.2205 0.5650 -0.1548 0.047 Uiso 1 1 calc R . . C015 N 1.1418(2) 0.46651(16) -0.09347(15) 0.0350(5) Uani 1 1 d . . . N1 N 0.8735(2) 0.24704(13) 0.04386(13) 0.0234(4) Uani 1 1 d . . . N2 N 0.6243(2) 0.31605(13) -0.04462(13) 0.0263(4) Uani 1 1 d . . . N3 N 0.8797(3) 0.53984(15) -0.18514(14) 0.0345(5) Uani 1 1 d . . . O1 O 0.33079(17) -0.13595(11) 0.10704(11) 0.0255(3) Uani 1 1 d . . . O2 O 0.26446(17) 0.01029(10) 0.11184(11) 0.0249(3) Uani 1 1 d . . . O3 O -0.23750(18) 0.07831(11) 0.08453(12) 0.0288(4) Uani 1 1 d . . . O4 O -0.38817(16) -0.01529(10) 0.13640(11) 0.0240(3) Uani 1 1 d . . . O5 O -0.1411(2) -0.25741(13) 0.33657(12) 0.0349(4) Uani 1 1 d . . . O6 O 0.03632(18) -0.33614(11) 0.29165(11) 0.0269(4) Uani 1 1 d . . . O7 O 0.45713(18) 0.14949(12) 0.01211(12) 0.0234(3) Uani 1 1 d . . . Zn1 Zn 0.65698(3) 0.195879(17) 0.035224(17) 0.02131(7) Uani 1 1 d . . . Zn2 Zn 0.44612(3) 0.070389(16) 0.111267(16) 0.01887(7) Uani 1 1 d . . . H7 H 0.449(4) 0.126(2) -0.026(2) 0.037(10) Uiso 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 C1 0.0160(10) 0.0227(11) 0.0181(10) 0.0010(8) 0.0050(8) -0.0030(8) C2 0.0170(10) 0.0163(9) 0.0199(10) -0.0025(8) 0.0071(8) -0.0013(8) C3 0.0164(10) 0.0166(10) 0.0234(10) 0.0007(8) 0.0054(8) 0.0027(8) C4 0.0190(10) 0.0169(10) 0.0204(10) 0.0026(8) 0.0059(8) 0.0010(8) C5 0.0182(10) 0.0206(10) 0.0245(11) 0.0046(9) 0.0051(8) 0.0003(8) C6 0.0167(10) 0.0183(10) 0.0250(11) 0.0029(8) 0.0093(8) 0.0001(8) C7 0.0149(10) 0.0168(10) 0.0200(10) -0.0010(8) 0.0047(8) -0.0006(8) C8 0.0174(10) 0.0161(9) 0.0198(10) 0.0024(8) 0.0061(8) -0.0010(8) C9 0.0174(10) 0.0188(10) 0.0160(10) -0.0011(8) 0.0033(8) 0.0010(8) C10 0.0316(14) 0.0238(12) 0.0384(14) 0.0032(10) 0.0043(11) 0.0005(10) C11 0.0250(13) 0.0322(14) 0.0529(17) 0.0064(12) 0.0011(11) 0.0054(11) C12 0.0242(13) 0.0362(14) 0.0469(15) 0.0014(12) 0.0120(11) -0.0019(11) C13 0.0257(12) 0.0254(12) 0.0283(12) -0.0019(9) 0.0100(9) -0.0032(9) C14 0.0255(12) 0.0181(10) 0.0253(11) -0.0024(8) 0.0090(9) -0.0016(9) C15 0.0263(12) 0.0200(11) 0.0259(11) -0.0016(9) 0.0095(9) -0.0017(9) C16 0.0236(13) 0.0435(16) 0.0539(17) 0.0157(13) 0.0124(12) 0.0017(12) C17 0.0311(16) 0.066(2) 0.070(2) 0.0367(18) 0.0070(15) 0.0108(15) C18 0.0401(16) 0.0507(18) 0.0499(18) 0.0287(14) 0.0054(13) 0.0005(14) C19 0.0317(13) 0.0271(12) 0.0285(12) 0.0036(10) 0.0081(10) -0.0004(10) C20 0.0353(14) 0.0264(12) 0.0232(11) -0.0015(9) 0.0109(10) -0.0072(10) C21 0.0306(13) 0.0289(12) 0.0252(12) -0.0041(10) 0.0118(10) -0.0076(10) C22 0.0511(17) 0.0323(13) 0.0295(13) 0.0031(11) 0.0160(12) -0.0114(12) C23 0.0426(16) 0.0420(15) 0.0383(15) 0.0018(12) 0.0198(12) -0.0152(13) C015 0.0330(12) 0.0379(12) 0.0368(12) 0.0010(10) 0.0135(10) -0.0103(10) N1 0.0235(10) 0.0184(9) 0.0289(10) 0.0004(8) 0.0067(8) -0.0013(7) N2 0.0246(10) 0.0221(10) 0.0344(11) 0.0039(8) 0.0111(8) 0.0002(8) N3 0.0452(14) 0.0319(11) 0.0281(11) 0.0060(9) 0.0113(10) -0.0060(10) O1 0.0195(8) 0.0266(8) 0.0332(9) -0.0007(7) 0.0116(7) 0.0037(7) O2 0.0165(8) 0.0197(8) 0.0399(9) 0.0023(7) 0.0091(7) -0.0039(6) O3 0.0199(8) 0.0205(8) 0.0480(10) 0.0121(7) 0.0114(7) 0.0033(6) O4 0.0166(8) 0.0211(8) 0.0364(9) 0.0064(7) 0.0104(6) 0.0026(6) O5 0.0303(10) 0.0420(10) 0.0377(10) 0.0197(8) 0.0200(8) 0.0113(8) O6 0.0302(9) 0.0220(8) 0.0304(9) 0.0080(7) 0.0108(7) 0.0069(7) O7 0.0214(8) 0.0259(9) 0.0237(9) 0.0002(7) 0.0060(7) -0.0024(7) Zn1 0.01837(13) 0.01700(13) 0.03072(15) 0.00360(10) 0.01013(10) 0.00033(10) Zn2 0.01531(12) 0.01642(12) 0.02650(14) -0.00114(10) 0.00807(9) -0.00117(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.236(3) . ? C1 O2 1.278(3) . ? C1 C2 1.507(3) . ? C2 C8 1.388(3) . ? C2 C3 1.393(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9300 . ? C4 C6 1.393(3) . ? C4 C5 1.511(3) . ? C5 O5 1.251(3) . ? C5 O6 1.267(3) . ? C6 C7 1.390(3) . ? C6 H6 0.9300 . ? C7 C8 1.390(3) . ? C7 C9 1.502(3) . ? C8 H8 0.9300 . ? C9 O3 1.241(3) . ? C9 O4 1.266(3) . ? C10 N1 1.336(3) . ? C10 C11 1.388(4) . ? C10 H10 0.9300 . ? C11 C12 1.368(4) . ? C11 H11 0.9300 . ? C12 C13 1.401(4) . ? C12 H12 0.9300 . ? C13 C14 1.397(3) . ? C13 C21 1.455(3) . ? C14 N1 1.350(3) . ? C14 C15 1.454(3) . ? C15 N2 1.353(3) . ? C15 C19 1.399(3) . ? C16 N2 1.316(3) . ? C16 C17 1.393(4) . ? C16 H16 0.9300 . ? C17 C18 1.367(4) . ? C17 H17 0.9300 . ? C18 C19 1.396(4) . ? C18 H18 0.9300 . ? C19 C20 1.453(3) . ? C20 N3 1.353(3) . ? C20 C21 1.399(4) . ? C21 C015 1.354(3) . ? C22 N3 1.318(3) . ? C22 C23 1.388(4) . ? C22 H22 0.9300 . ? C23 C015 1.322(4) . ? C23 H23 0.9300 . ? N1 Zn1 2.159(2) . ? N2 Zn1 2.131(2) . ? O1 Zn1 2.3604(16) 3_655 ? O2 Zn2 1.9318(15) . ? O3 Zn1 2.0614(16) 1_455 ? O4 Zn2 1.9875(16) 1_455 ? O5 Zn1 2.1006(17) 2_545 ? O6 Zn2 1.9999(16) 2_545 ? O7 Zn2 1.9230(17) . ? O7 Zn1 1.9742(17) . ? O7 H7 0.67(3) . ? Zn1 O3 2.0614(16) 1_655 ? Zn1 O5 2.1006(17) 2 ? Zn1 O1 2.3604(16) 3_655 ? Zn1 Zn2 3.0980(6) . ? Zn2 O4 1.9875(16) 1_655 ? Zn2 O6 1.9999(16) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 126.2(2) . . ? O1 C1 C2 119.25(19) . . ? O2 C1 C2 114.51(18) . . ? C8 C2 C3 119.53(19) . . ? C8 C2 C1 119.27(18) . . ? C3 C2 C1 121.01(19) . . ? C2 C3 C4 120.18(19) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C6 C4 C3 119.55(19) . . ? C6 C4 C5 118.82(19) . . ? C3 C4 C5 121.37(19) . . ? O5 C5 O6 126.5(2) . . ? O5 C5 C4 115.96(19) . . ? O6 C5 C4 117.47(19) . . ? C7 C6 C4 120.43(19) . . ? C7 C6 H6 119.8 . . ? C4 C6 H6 119.8 . . ? C6 C7 C8 119.46(19) . . ? C6 C7 C9 121.57(18) . . ? C8 C7 C9 118.76(18) . . ? C2 C8 C7 120.75(19) . . ? C2 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? O3 C9 O4 125.6(2) . . ? O3 C9 C7 116.41(19) . . ? O4 C9 C7 117.95(18) . . ? N1 C10 C11 123.0(2) . . ? N1 C10 H10 118.5 . . ? C11 C10 H10 118.5 . . ? C12 C11 C10 119.3(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.4(2) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 117.5(2) . . ? C14 C13 C21 119.0(2) . . ? C12 C13 C21 123.5(2) . . ? N1 C14 C13 123.1(2) . . ? N1 C14 C15 116.4(2) . . ? C13 C14 C15 120.5(2) . . ? N2 C15 C19 122.2(2) . . ? N2 C15 C14 117.3(2) . . ? C19 C15 C14 120.5(2) . . ? N2 C16 C17 122.6(3) . . ? N2 C16 H16 118.7 . . ? C17 C16 H16 118.7 . . ? C18 C17 C16 119.1(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C15 117.6(2) . . ? C18 C19 C20 123.4(2) . . ? C15 C19 C20 119.1(2) . . ? N3 C20 C21 121.3(2) . . ? N3 C20 C19 118.2(2) . . ? C21 C20 C19 120.4(2) . . ? C015 C21 C20 121.6(2) . . ? C015 C21 C13 117.9(2) . . ? C20 C21 C13 120.5(2) . . ? N3 C22 C23 122.1(2) . . ? N3 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C015 C23 C22 123.2(2) . . ? C015 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? C23 C015 C21 115.5(2) . . ? C10 N1 C14 117.7(2) . . ? C10 N1 Zn1 127.92(16) . . ? C14 N1 Zn1 113.87(15) . . ? C16 N2 C15 118.9(2) . . ? C16 N2 Zn1 126.11(17) . . ? C15 N2 Zn1 114.23(16) . . ? C22 N3 C20 116.4(2) . . ? C1 O1 Zn1 122.31(14) . 3_655 ? C1 O2 Zn2 126.34(14) . . ? C9 O3 Zn1 137.83(15) . 1_455 ? C9 O4 Zn2 121.18(14) . 1_455 ? C5 O5 Zn1 133.08(15) . 2_545 ? C5 O6 Zn2 121.49(14) . 2_545 ? Zn2 O7 Zn1 105.29(9) . . ? Zn2 O7 H7 110(3) . . ? Zn1 O7 H7 106(3) . . ? O7 Zn1 O3 98.89(7) . 1_655 ? O7 Zn1 O5 92.32(8) . 2 ? O3 Zn1 O5 92.97(8) 1_655 2 ? O7 Zn1 N2 98.97(8) . . ? O3 Zn1 N2 155.21(7) 1_655 . ? O5 Zn1 N2 103.33(8) 2 . ? O7 Zn1 N1 173.35(7) . . ? O3 Zn1 N1 83.31(7) 1_655 . ? O5 Zn1 N1 93.83(7) 2 . ? N2 Zn1 N1 77.16(8) . . ? O7 Zn1 O1 85.57(7) . 3_655 ? O3 Zn1 O1 85.15(7) 1_655 3_655 ? O5 Zn1 O1 176.92(6) 2 3_655 ? N2 Zn1 O1 79.24(7) . 3_655 ? N1 Zn1 O1 88.38(7) . 3_655 ? O7 Zn1 Zn2 36.78(5) . . ? O3 Zn1 Zn2 70.52(5) 1_655 . ? O5 Zn1 Zn2 71.38(5) 2 . ? N2 Zn1 Zn2 132.28(6) . . ? N1 Zn1 Zn2 148.70(5) . . ? O1 Zn1 Zn2 105.66(4) 3_655 . ? O7 Zn2 O2 117.55(7) . . ? O7 Zn2 O4 111.92(7) . 1_655 ? O2 Zn2 O4 112.19(7) . 1_655 ? O7 Zn2 O6 98.96(8) . 2 ? O2 Zn2 O6 104.90(7) . 2 ? O4 Zn2 O6 110.04(7) 1_655 2 ? O7 Zn2 Zn1 37.93(5) . . ? O2 Zn2 Zn1 155.47(5) . . ? O4 Zn2 Zn1 84.77(5) 1_655 . ? O6 Zn2 Zn1 84.27(5) 2 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.468 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.082