# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Juyoung Yoon' _publ_contact_author_email JYOON@EWHA.AC.KR _publ_section_title ; Pyrophosphate Selective Fluorescent Chemosensors Based on Coumarin-DPA-Cu(II) Complexes ; loop_ _publ_author_name 'Juyoung Yoon' 'Min Jung Kim' 'Youngmee Kim' 'Sung-Jin Kim' 'Kyung Mi Lee' 'K. M. K. Swamy' # Attachment '737519_revised_090914_.cif' data_CuNO3Cu _database_code_depnum_ccdc_archive 'CCDC 737519' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 Cu2 N10 O20' _chemical_formula_weight 1157.96 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4488(8) _cell_length_b 8.4998(8) _cell_length_c 17.5045(16) _cell_angle_alpha 83.423(2) _cell_angle_beta 81.649(2) _cell_angle_gamma 79.468(2) _cell_volume 1217.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1924 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 22.79 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6753 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0887 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4616 _reflns_number_gt 3099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Oxygen atoms attached to N4, N5, and N6 atoms in nitrate anions were fixed and treated as riding with N-O = 1.25 \%A. Oxygen atoms attached to N6 were fixed geometrically and treated as riding with O...O = 2.15 \%A. Hydrogen atoms attached to O4 atom were treated as riding with 0.93 \%A and U~iso~(H) = 1.2U~eq~(C). 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^)+(0.0982P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4616 _refine_ls_number_parameters 386 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1771 _refine_ls_wR_factor_gt 0.1697 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.1849(6) -0.1102(6) 0.3627(2) 0.0368(11) Uani 1 1 d . . . C3 C 0.3515(6) -0.1955(6) 0.3356(3) 0.0395(11) Uani 1 1 d . . . H3A H 0.4101 -0.2320 0.3799 0.047 Uiso 1 1 calc R . . H3B H 0.3432 -0.2890 0.3105 0.047 Uiso 1 1 calc R . . C4 C 0.6198(6) -0.1245(6) 0.2810(3) 0.0368(11) Uani 1 1 d . . . H4A H 0.6674 -0.2015 0.2437 0.044 Uiso 1 1 calc R . . H4B H 0.6442 -0.1719 0.3320 0.044 Uiso 1 1 calc R . . C5 C 0.6917(6) 0.0287(6) 0.2605(2) 0.0345(10) Uani 1 1 d . . . C6 C 0.8493(6) 0.0305(7) 0.2245(3) 0.0485(13) Uani 1 1 d . . . H6 H 0.9157 -0.0639 0.2098 0.058 Uiso 1 1 calc R . . C7 C 0.9057(7) 0.1766(7) 0.2109(3) 0.0529(15) Uani 1 1 d . . . H7 H 1.0107 0.1815 0.1870 0.064 Uiso 1 1 calc R . . C8 C 0.3997(6) -0.0969(5) 0.2009(2) 0.0329(10) Uani 1 1 d . . . H8A H 0.4219 -0.2085 0.1896 0.040 Uiso 1 1 calc R . . H8B H 0.2842 -0.0592 0.2006 0.040 Uiso 1 1 calc R . . C9 C 0.4908(5) -0.0005(5) 0.1377(2) 0.0304(10) Uani 1 1 d . . . C10 C 0.4510(6) 0.1659(5) 0.1280(2) 0.0332(10) Uani 1 1 d . . . C12 C 0.6193(6) -0.0727(5) 0.0878(2) 0.0319(10) Uani 1 1 d . . . C14 C 0.0245(6) 0.1375(6) 0.3871(3) 0.0428(12) Uani 1 1 d . . . H14 H 0.0134 0.2487 0.3849 0.051 Uiso 1 1 calc R . . C15 C 0.5345(6) 0.2555(6) 0.0702(3) 0.0409(12) Uani 1 1 d . . . H15 H 0.5048 0.3666 0.0640 0.049 Uiso 1 1 calc R . . C16 C 0.6615(6) 0.1795(6) 0.0222(3) 0.0429(12) Uani 1 1 d . . . H16 H 0.7191 0.2404 -0.0157 0.052 Uiso 1 1 calc R . . C17 C 0.7056(6) 0.0132(6) 0.0291(2) 0.0352(11) Uani 1 1 d . . . C18 C 0.8044(7) 0.3125(7) 0.2332(3) 0.0550(15) Uani 1 1 d . . . H18 H 0.8396 0.4112 0.2244 0.066 Uiso 1 1 calc R . . C19 C 0.6512(7) 0.3027(6) 0.2686(3) 0.0472(13) Uani 1 1 d . . . H19 H 0.5834 0.3959 0.2839 0.057 Uiso 1 1 calc R . . C20 C 0.0552(7) -0.1883(6) 0.3922(3) 0.0458(13) Uani 1 1 d . . . H20 H 0.0665 -0.2992 0.3923 0.055 Uiso 1 1 calc R . . C21 C -0.0895(6) -0.1005(7) 0.4210(3) 0.0497(14) Uani 1 1 d . . . H21 H -0.1758 -0.1523 0.4423 0.060 Uiso 1 1 calc R . . C22 C -0.1069(6) 0.0639(7) 0.4186(3) 0.0489(13) Uani 1 1 d . . . H22 H -0.2048 0.1246 0.4377 0.059 Uiso 1 1 calc R . . C23 C 0.8375(6) -0.0761(7) -0.0187(3) 0.0426(12) Uani 1 1 d . . . H23 H 0.8962 -0.0213 -0.0588 0.051 Uiso 1 1 calc R . . C24 C 0.8763(6) -0.2323(7) -0.0068(3) 0.0481(13) Uani 1 1 d . . . H24 H 0.9648 -0.2851 -0.0375 0.058 Uiso 1 1 calc R . . C25 C 0.7844(7) -0.3269(7) 0.0534(3) 0.0519(14) Uani 1 1 d . . . Cu1 Cu 0.37066(7) 0.13327(7) 0.31971(3) 0.0349(2) Uani 1 1 d . . . N1 N 0.1678(5) 0.0520(5) 0.3597(2) 0.0348(9) Uani 1 1 d . . . N2 N 0.4422(4) -0.0873(4) 0.28053(19) 0.0299(8) Uani 1 1 d . . . N3 N 0.5949(5) 0.1618(5) 0.2821(2) 0.0364(9) Uani 1 1 d . . . O1 O 0.3254(4) 0.2334(4) 0.17862(17) 0.0400(8) Uani 1 1 d . . . H1 H 0.3058 0.3306 0.1671 0.060 Uiso 1 1 calc R . . O2 O 0.6587(4) -0.2386(4) 0.09928(17) 0.0396(8) Uani 1 1 d . . . O3 O 0.8043(6) -0.4706(5) 0.0675(3) 0.0782(14) Uani 1 1 d . . . O4 O 0.2902(5) 0.3572(4) 0.3438(2) 0.0528(10) Uani 1 1 d D . . H4C H 0.303(7) 0.363(7) 0.3952(10) 0.063 Uiso 1 1 d D . . H4D H 0.245(6) 0.430(5) 0.306(2) 0.063 Uiso 1 1 d D . . N4 N 0.503(10) 0.9800(13) 0.5062(19) 0.042(3) Uani 0.50 1 d PD A -1 O5 O 0.4556(19) 1.0735(16) 0.4504(7) 0.092(4) Uani 0.50 1 d PD A -1 O6 O 0.4700(19) 0.9771(18) 0.4391(5) 0.087(4) Uani 0.50 1 d PD A -1 O7 O 0.5147(14) 0.8359(13) 0.4940(8) 0.111(4) Uani 0.50 1 d PD A -1 N5 N 0.1432(5) 0.6085(5) 0.1867(3) 0.0661(14) Uani 1 1 d D . . O8 O 0.0854(6) 0.5536(6) 0.2517(3) 0.0869(15) Uani 1 1 d D . . O9 O 0.0723(7) 0.7305(6) 0.1513(3) 0.112(2) Uani 1 1 d D . . O10 O 0.2806(6) 0.5446(6) 0.1582(4) 0.123(2) Uani 1 1 d D . . N6 N 0.2548(7) 0.4939(8) 0.5203(3) 0.037(2) Uani 0.50 1 d PD . . O11 O 0.3581(6) 0.5034(7) 0.4624(3) 0.0298(13) Uani 0.50 1 d PD . . O12 O 0.1189(8) 0.4656(16) 0.5121(6) 0.177(8) Uani 0.50 1 d PD . . O13 O 0.2923(12) 0.4923(16) 0.5863(3) 0.161(6) Uani 0.50 1 d PD . . 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 C2 0.041(3) 0.046(3) 0.023(2) -0.001(2) 0.000(2) -0.010(2) C3 0.045(3) 0.034(3) 0.035(3) 0.005(2) 0.004(2) -0.007(2) C4 0.033(3) 0.039(3) 0.036(3) -0.004(2) -0.005(2) 0.001(2) C5 0.032(3) 0.048(3) 0.025(2) -0.003(2) -0.0047(19) -0.007(2) C6 0.037(3) 0.067(4) 0.042(3) -0.008(3) -0.005(2) -0.009(3) C7 0.042(3) 0.083(4) 0.038(3) 0.001(3) -0.003(2) -0.025(3) C8 0.033(3) 0.036(3) 0.031(2) -0.0097(19) 0.001(2) -0.011(2) C9 0.031(2) 0.036(3) 0.025(2) -0.0057(18) -0.0058(19) -0.0047(19) C10 0.037(3) 0.039(3) 0.025(2) -0.0035(19) -0.010(2) -0.003(2) C12 0.036(3) 0.037(3) 0.025(2) -0.0049(19) -0.008(2) -0.007(2) C14 0.037(3) 0.055(3) 0.036(3) -0.012(2) 0.001(2) -0.006(2) C15 0.048(3) 0.036(3) 0.037(3) 0.001(2) -0.004(2) -0.007(2) C16 0.050(3) 0.046(3) 0.032(3) 0.004(2) -0.001(2) -0.016(2) C17 0.034(3) 0.044(3) 0.028(2) -0.004(2) -0.007(2) -0.007(2) C18 0.056(4) 0.064(4) 0.052(3) 0.004(3) -0.007(3) -0.034(3) C19 0.046(3) 0.044(3) 0.054(3) -0.003(2) -0.009(3) -0.014(2) C20 0.050(3) 0.054(3) 0.036(3) -0.001(2) 0.001(2) -0.022(3) C21 0.036(3) 0.075(4) 0.041(3) -0.001(3) -0.002(2) -0.023(3) C22 0.033(3) 0.074(4) 0.037(3) -0.005(3) 0.002(2) -0.008(3) C23 0.037(3) 0.060(3) 0.030(2) -0.006(2) 0.001(2) -0.009(2) C24 0.039(3) 0.060(4) 0.040(3) -0.014(3) 0.005(2) 0.002(3) C25 0.051(3) 0.054(4) 0.044(3) -0.013(3) 0.002(3) 0.009(3) Cu1 0.0344(4) 0.0337(4) 0.0371(4) -0.0093(2) 0.0016(2) -0.0075(2) N1 0.031(2) 0.043(2) 0.030(2) -0.0056(17) 0.0020(17) -0.0091(17) N2 0.029(2) 0.031(2) 0.0278(19) -0.0016(15) 0.0000(16) -0.0054(16) N3 0.037(2) 0.042(2) 0.033(2) -0.0061(17) -0.0050(18) -0.0111(18) O1 0.045(2) 0.0345(18) 0.0367(18) -0.0060(14) 0.0007(16) 0.0011(15) O2 0.042(2) 0.0343(18) 0.0373(18) -0.0058(14) 0.0044(15) 0.0000(14) O3 0.087(3) 0.043(3) 0.085(3) -0.008(2) 0.027(3) 0.009(2) O4 0.069(3) 0.040(2) 0.051(2) -0.0150(17) -0.013(2) -0.0003(18) N4 0.035(6) 0.061(7) 0.024(9) 0.015(9) 0.004(10) -0.007(17) O5 0.139(11) 0.114(11) 0.033(6) 0.007(7) -0.039(7) -0.031(10) O6 0.123(10) 0.113(10) 0.039(6) -0.027(7) -0.028(6) -0.029(9) O7 0.108(10) 0.072(8) 0.150(12) -0.033(8) -0.026(8) 0.015(6) N5 0.074(4) 0.039(3) 0.086(4) -0.018(3) -0.012(3) -0.005(3) O8 0.087(4) 0.092(4) 0.076(3) -0.005(3) -0.006(3) -0.009(3) O9 0.139(5) 0.079(4) 0.092(4) 0.001(3) -0.020(4) 0.046(3) O10 0.095(4) 0.048(3) 0.193(6) 0.007(3) 0.049(4) 0.011(3) N6 0.044(5) 0.018(4) 0.056(5) 0.009(4) -0.032(5) -0.006(3) O11 0.029(3) 0.036(3) 0.022(3) 0.012(2) -0.007(3) -0.006(3) O12 0.136(13) 0.163(14) 0.223(16) 0.120(13) -0.063(12) -0.056(11) O13 0.123(12) 0.120(11) 0.214(16) -0.043(11) 0.021(12) 0.032(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 C2 N1 1.355(6) . ? C2 C20 1.390(7) . ? C2 C3 1.498(7) . ? C3 N2 1.484(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.477(6) . ? C4 C5 1.521(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N3 1.327(6) . ? C5 C6 1.390(7) . ? C6 C7 1.394(7) . ? C6 H6 0.9300 . ? C7 C18 1.365(8) . ? C7 H7 0.9300 . ? C8 C9 1.504(6) . ? C8 N2 1.505(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.386(6) . ? C9 C10 1.389(6) . ? C10 O1 1.365(5) . ? C10 C15 1.383(6) . ? C12 C17 1.387(6) . ? C12 O2 1.387(5) . ? C14 N1 1.347(6) . ? C14 C22 1.388(7) . ? C14 H14 0.9300 . ? C15 C16 1.372(7) . ? C15 H15 0.9300 . ? C16 C17 1.390(7) . ? C16 H16 0.9300 . ? C17 C23 1.444(7) . ? C18 C19 1.364(7) . ? C18 H18 0.9300 . ? C19 N3 1.352(6) . ? C19 H19 0.9300 . ? C20 C21 1.371(8) . ? C20 H20 0.9300 . ? C21 C22 1.375(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.307(7) . ? C23 H23 0.9300 . ? C24 C25 1.469(8) . ? C24 H24 0.9300 . ? C25 O3 1.204(6) . ? C25 O2 1.391(6) . ? Cu1 N3 1.962(4) . ? Cu1 N1 1.969(4) . ? Cu1 O4 1.973(3) . ? Cu1 N2 2.027(3) . ? O1 H1 0.8200 . ? O4 H4C 0.93(3) . ? O4 H4D 0.93(4) . ? N4 O6 1.249(2) . ? N4 O7 1.251(2) . ? N4 O5 1.251(2) . ? O5 O6 0.847(14) . ? O6 O7 1.478(17) . ? N5 O9 1.246(7) . ? N5 O8 1.245(7) . ? N5 O10 1.247(7) . ? N6 O13 1.2394(18) . ? N6 O11 1.2437(18) . ? N6 O12 1.2469(18) . ? 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 C2 C20 120.6(5) . . ? N1 C2 C3 115.6(4) . . ? C20 C2 C3 123.8(5) . . ? N2 C3 C2 110.6(4) . . ? N2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C5 109.6(4) . . ? N2 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N3 C5 C6 121.7(4) . . ? N3 C5 C4 115.1(4) . . ? C6 C5 C4 123.1(4) . . ? C5 C6 C7 118.6(5) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C18 C7 C6 118.9(5) . . ? C18 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 N2 113.8(3) . . ? C9 C8 H8A 108.8 . . ? N2 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? N2 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C12 C9 C10 117.1(4) . . ? C12 C9 C8 121.8(4) . . ? C10 C9 C8 121.0(4) . . ? O1 C10 C15 122.9(4) . . ? O1 C10 C9 115.7(4) . . ? C15 C10 C9 121.4(4) . . ? C9 C12 C17 123.1(4) . . ? C9 C12 O2 116.2(4) . . ? C17 C12 O2 120.7(4) . . ? N1 C14 C22 121.7(5) . . ? N1 C14 H14 119.1 . . ? C22 C14 H14 119.1 . . ? C16 C15 C10 119.6(5) . . ? C16 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? C15 C16 C17 121.3(4) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 117.5(4) . . ? C12 C17 C23 117.7(4) . . ? C16 C17 C23 124.8(4) . . ? C19 C18 C7 119.7(5) . . ? C19 C18 H18 120.2 . . ? C7 C18 H18 120.2 . . ? N3 C19 C18 122.0(5) . . ? N3 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C21 C20 C2 119.5(5) . . ? C21 C20 H20 120.3 . . ? C2 C20 H20 120.3 . . ? C20 C21 C22 120.0(5) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C14 118.6(5) . . ? C21 C22 H22 120.7 . . ? C14 C22 H22 120.7 . . ? C24 C23 C17 121.5(5) . . ? C24 C23 H23 119.3 . . ? C17 C23 H23 119.3 . . ? C23 C24 C25 122.1(5) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? O3 C25 O2 116.5(5) . . ? O3 C25 C24 128.0(5) . . ? O2 C25 C24 115.6(5) . . ? N3 Cu1 N1 166.81(16) . . ? N3 Cu1 O4 96.33(16) . . ? N1 Cu1 O4 96.21(16) . . ? N3 Cu1 N2 84.27(15) . . ? N1 Cu1 N2 83.86(15) . . ? O4 Cu1 N2 172.09(14) . . ? C14 N1 C2 119.5(4) . . ? C14 N1 Cu1 127.4(3) . . ? C2 N1 Cu1 113.0(3) . . ? C4 N2 C3 113.8(4) . . ? C4 N2 C8 110.6(3) . . ? C3 N2 C8 107.7(3) . . ? C4 N2 Cu1 105.9(3) . . ? C3 N2 Cu1 105.1(3) . . ? C8 N2 Cu1 113.7(3) . . ? C5 N3 C19 119.1(4) . . ? C5 N3 Cu1 114.1(3) . . ? C19 N3 Cu1 126.4(4) . . ? C10 O1 H1 109.5 . . ? C12 O2 C25 122.4(4) . . ? Cu1 O4 H4C 108(4) . . ? Cu1 O4 H4D 118(4) . . ? H4C O4 H4D 134(5) . . ? O6 N4 O7 72.5(10) . . ? O6 N4 O5 39.6(7) . . ? O7 N4 O5 112.0(10) . . ? O6 O5 N4 70.1(4) . . ? O5 O6 N4 70.3(4) . . ? O5 O6 O7 123.9(7) . . ? N4 O6 O7 53.8(5) . . ? N4 O7 O6 53.7(5) . . ? O9 N5 O8 122.1(5) . . ? O9 N5 O10 118.9(5) . . ? O8 N5 O10 118.8(5) . . ? O13 N6 O11 120.5(2) . . ? O13 N6 O12 119.8(2) . . ? O11 N6 O12 119.1(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 N1 C2 C3 N2 -25.0(6) . . . . ? C20 C2 C3 N2 157.5(4) . . . . ? N2 C4 C5 N3 30.8(5) . . . . ? N2 C4 C5 C6 -151.6(4) . . . . ? N3 C5 C6 C7 -0.1(7) . . . . ? C4 C5 C6 C7 -177.5(4) . . . . ? C5 C6 C7 C18 -0.1(7) . . . . ? N2 C8 C9 C12 103.9(5) . . . . ? N2 C8 C9 C10 -74.9(5) . . . . ? C12 C9 C10 O1 -179.2(4) . . . . ? C8 C9 C10 O1 -0.3(6) . . . . ? C12 C9 C10 C15 0.9(6) . . . . ? C8 C9 C10 C15 179.8(4) . . . . ? C10 C9 C12 C17 -1.0(6) . . . . ? C8 C9 C12 C17 -179.9(4) . . . . ? C10 C9 C12 O2 179.0(4) . . . . ? C8 C9 C12 O2 0.1(6) . . . . ? O1 C10 C15 C16 178.9(4) . . . . ? C9 C10 C15 C16 -1.2(7) . . . . ? C10 C15 C16 C17 1.6(7) . . . . ? C9 C12 C17 C16 1.4(7) . . . . ? O2 C12 C17 C16 -178.6(4) . . . . ? C9 C12 C17 C23 179.6(4) . . . . ? O2 C12 C17 C23 -0.4(6) . . . . ? C15 C16 C17 C12 -1.7(7) . . . . ? C15 C16 C17 C23 -179.8(5) . . . . ? C6 C7 C18 C19 0.4(8) . . . . ? C7 C18 C19 N3 -0.4(8) . . . . ? N1 C2 C20 C21 -2.4(7) . . . . ? C3 C2 C20 C21 175.0(4) . . . . ? C2 C20 C21 C22 1.9(7) . . . . ? C20 C21 C22 C14 -0.5(7) . . . . ? N1 C14 C22 C21 -0.5(7) . . . . ? C12 C17 C23 C24 -0.8(7) . . . . ? C16 C17 C23 C24 177.2(5) . . . . ? C17 C23 C24 C25 2.6(8) . . . . ? C23 C24 C25 O3 176.7(6) . . . . ? C23 C24 C25 O2 -3.0(8) . . . . ? C22 C14 N1 C2 0.0(7) . . . . ? C22 C14 N1 Cu1 -175.5(3) . . . . ? C20 C2 N1 C14 1.5(6) . . . . ? C3 C2 N1 C14 -176.1(4) . . . . ? C20 C2 N1 Cu1 177.6(3) . . . . ? C3 C2 N1 Cu1 0.0(5) . . . . ? N3 Cu1 N1 C14 166.6(5) . . . . ? O4 Cu1 N1 C14 4.7(4) . . . . ? N2 Cu1 N1 C14 -167.3(4) . . . . ? N3 Cu1 N1 C2 -9.2(8) . . . . ? O4 Cu1 N1 C2 -171.1(3) . . . . ? N2 Cu1 N1 C2 16.9(3) . . . . ? C5 C4 N2 C3 -149.8(4) . . . . ? C5 C4 N2 C8 88.8(4) . . . . ? C5 C4 N2 Cu1 -34.8(4) . . . . ? C2 C3 N2 C4 151.1(4) . . . . ? C2 C3 N2 C8 -86.0(4) . . . . ? C2 C3 N2 Cu1 35.6(4) . . . . ? C9 C8 N2 C4 -51.5(5) . . . . ? C9 C8 N2 C3 -176.5(4) . . . . ? C9 C8 N2 Cu1 67.4(4) . . . . ? N3 Cu1 N2 C4 24.7(3) . . . . ? N1 Cu1 N2 C4 -149.6(3) . . . . ? O4 Cu1 N2 C4 119.5(11) . . . . ? N3 Cu1 N2 C3 145.4(3) . . . . ? N1 Cu1 N2 C3 -28.8(3) . . . . ? O4 Cu1 N2 C3 -119.8(11) . . . . ? N3 Cu1 N2 C8 -97.0(3) . . . . ? N1 Cu1 N2 C8 88.8(3) . . . . ? O4 Cu1 N2 C8 -2.2(12) . . . . ? C6 C5 N3 C19 0.0(6) . . . . ? C4 C5 N3 C19 177.6(4) . . . . ? C6 C5 N3 Cu1 172.8(3) . . . . ? C4 C5 N3 Cu1 -9.6(5) . . . . ? C18 C19 N3 C5 0.2(7) . . . . ? C18 C19 N3 Cu1 -171.6(4) . . . . ? N1 Cu1 N3 C5 17.1(8) . . . . ? O4 Cu1 N3 C5 179.0(3) . . . . ? N2 Cu1 N3 C5 -9.0(3) . . . . ? N1 Cu1 N3 C19 -170.7(6) . . . . ? O4 Cu1 N3 C19 -8.9(4) . . . . ? N2 Cu1 N3 C19 163.2(4) . . . . ? C9 C12 O2 C25 179.8(4) . . . . ? C17 C12 O2 C25 -0.2(6) . . . . ? O3 C25 O2 C12 -178.0(5) . . . . ? C24 C25 O2 C12 1.8(7) . . . . ? O7 N4 O5 O6 -5(5) . . . . ? N4 O5 O6 O7 4(5) . . . . ? O7 N4 O6 O5 175(5) . . . . ? O5 N4 O6 O7 -175(5) . . . . ? O5 N4 O7 O6 3(3) . . . . ? O5 O6 O7 N4 -5(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4D O8 0.930(2) 1.86(2) 2.742(6) 158(5) . O4 H4C O11 0.930(2) 1.92(3) 2.716(6) 142(5) . O1 H1 O10 0.82 1.78 2.593(6) 169.0 . _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.189 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.130 # Attachment '2-Cu.cif' data_ym99p212121 _database_code_depnum_ccdc_archive 'CCDC 737520' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H19 Cu N5 O9' _chemical_formula_weight 560.96 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.8036(10) _cell_length_b 13.0269(15) _cell_length_c 19.063(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2186.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 2392 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 24.21 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 1.068 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12120 _diffrn_reflns_av_R_equivalents 0.0707 _diffrn_reflns_av_sigmaI/netI 0.1112 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4295 _reflns_number_gt 2985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0244P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.006(14) _refine_ls_number_reflns 4295 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0698 _refine_ls_goodness_of_fit_ref 0.838 _refine_ls_restrained_S_all 0.838 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.56246(6) 0.42097(4) 0.16546(3) 0.02281(13) Uani 1 1 d . . . N1 N 0.6776(4) 0.5508(2) 0.16642(18) 0.0217(8) Uani 1 1 d . . . N2 N 0.3950(4) 0.5072(2) 0.12448(15) 0.0203(9) Uani 1 1 d . . . N3 N 0.4086(4) 0.3126(2) 0.16064(17) 0.0221(8) Uani 1 1 d . . . C1 C 0.8251(5) 0.5617(3) 0.1726(2) 0.0264(10) Uani 1 1 d . . . H1 H 0.8856 0.5021 0.1792 0.032 Uiso 1 1 calc R . . C2 C 0.8964(5) 0.6561(3) 0.1699(2) 0.0317(11) Uani 1 1 d . . . H2 H 1.0037 0.6618 0.1737 0.038 Uiso 1 1 calc R . . C3 C 0.8063(5) 0.7417(3) 0.1616(2) 0.0352(11) Uani 1 1 d . . . H3 H 0.8512 0.8080 0.1608 0.042 Uiso 1 1 calc R . . C4 C 0.6541(5) 0.7317(3) 0.1547(2) 0.0273(10) Uani 1 1 d . . . H4 H 0.5922 0.7907 0.1481 0.033 Uiso 1 1 calc R . . C5 C 0.5886(5) 0.6346(3) 0.1573(2) 0.0197(9) Uani 1 1 d . . . C6 C 0.4206(5) 0.6136(3) 0.1522(2) 0.0252(10) Uani 1 1 d . . . H6A H 0.3735 0.6204 0.1991 0.030 Uiso 1 1 calc R . . H6B H 0.3726 0.6644 0.1205 0.030 Uiso 1 1 calc R . . C7 C 0.2500(4) 0.4623(3) 0.1495(2) 0.0248(11) Uani 1 1 d . . . H7A H 0.1664 0.4811 0.1172 0.030 Uiso 1 1 calc R . . H7B H 0.2253 0.4893 0.1967 0.030 Uiso 1 1 calc R . . C8 C 0.2670(5) 0.3460(3) 0.1524(2) 0.0222(10) Uani 1 1 d . . . C9 C 0.1422(5) 0.2800(3) 0.1496(2) 0.0314(12) Uani 1 1 d . . . H9 H 0.0422 0.3059 0.1433 0.038 Uiso 1 1 calc R . . C10 C 0.1684(6) 0.1758(3) 0.1560(2) 0.0401(13) Uani 1 1 d . . . H10 H 0.0860 0.1288 0.1541 0.048 Uiso 1 1 calc R . . C11 C 0.3131(6) 0.1406(3) 0.1652(2) 0.0360(11) Uani 1 1 d . . . H11 H 0.3319 0.0691 0.1701 0.043 Uiso 1 1 calc R . . C12 C 0.4329(6) 0.2103(3) 0.1673(2) 0.0309(10) Uani 1 1 d . . . H12 H 0.5336 0.1857 0.1735 0.037 Uiso 1 1 calc R . . C13 C 0.3929(4) 0.5038(3) 0.04557(18) 0.0190(10) Uani 1 1 d . . . H13A H 0.3855 0.4313 0.0304 0.023 Uiso 1 1 calc R . . H13B H 0.3008 0.5398 0.0287 0.023 Uiso 1 1 calc R . . C14 C 0.5289(5) 0.5512(3) 0.01185(18) 0.0202(10) Uani 1 1 d . . . C15 C 0.5224(5) 0.6495(3) -0.0105(2) 0.0241(11) Uani 1 1 d . . . H15 H 0.4265 0.6830 -0.0110 0.029 Uiso 1 1 calc R . . C16 C 0.6535(6) 0.7060(3) -0.0336(2) 0.0260(11) Uani 1 1 d . . . C17 C 0.8001(5) 0.5505(3) -0.02064(19) 0.0198(10) Uani 1 1 d . . . C18 C 0.9385(5) 0.5065(3) -0.02916(19) 0.0240(9) Uani 1 1 d . . . H18 H 1.0210 0.5456 -0.0471 0.029 Uiso 1 1 calc R . . C19 C 0.9589(5) 0.4032(3) -0.01132(19) 0.0251(10) Uani 1 1 d . . . C20 C 0.8365(5) 0.3479(3) 0.0156(2) 0.0245(11) Uani 1 1 d . . . H20 H 0.8507 0.2785 0.0293 0.029 Uiso 1 1 calc R . . C21 C 0.6952(5) 0.3925(3) 0.0226(2) 0.0235(11) Uani 1 1 d . . . H21 H 0.6127 0.3525 0.0394 0.028 Uiso 1 1 calc R . . C22 C 0.6712(5) 0.4969(3) 0.00503(19) 0.0204(10) Uani 1 1 d . . . O1 O 0.6565(4) 0.7974(2) -0.04822(15) 0.0324(8) Uani 1 1 d . . . O2 O 0.7874(3) 0.6533(2) -0.03887(14) 0.0242(7) Uani 1 1 d . . . O3 O 1.0913(4) 0.3536(2) -0.02048(15) 0.0322(8) Uani 1 1 d . . . H3A H 1.1493 0.3895 -0.0455 0.048 Uiso 1 1 calc R . . N11 N 0.7364(5) 0.3378(3) 0.2598(2) 0.0362(10) Uani 1 1 d . . . O11 O 0.7357(4) 0.3339(2) 0.19312(16) 0.0347(8) Uani 1 1 d . . . O12 O 0.6321(4) 0.3869(2) 0.28884(16) 0.0459(10) Uani 1 1 d . . . O13 O 0.8387(5) 0.2975(3) 0.29335(19) 0.0724(13) Uani 1 1 d . . . N21 N 0.7922(5) 0.0300(2) 0.1583(2) 0.0316(9) Uani 1 1 d . . . O21 O 0.8141(4) 0.0678(3) 0.09820(14) 0.0492(9) Uani 1 1 d . . . O22 O 0.9017(4) 0.0030(3) 0.19406(15) 0.0462(9) Uani 1 1 d . . . O23 O 0.6611(4) 0.0176(2) 0.17942(17) 0.0512(10) 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 Cu1 0.0235(3) 0.0206(2) 0.0243(2) 0.0013(3) -0.0018(3) 0.0006(3) N1 0.019(2) 0.026(2) 0.0199(17) -0.0027(18) -0.0038(19) -0.0032(14) N2 0.023(2) 0.024(2) 0.0141(17) -0.0042(15) 0.0003(15) -0.0047(15) N3 0.028(2) 0.0210(18) 0.0176(17) 0.0058(17) -0.002(2) -0.0011(15) C1 0.024(3) 0.029(3) 0.027(2) 0.001(2) 0.000(2) -0.0001(19) C2 0.020(3) 0.041(3) 0.035(3) 0.001(3) 0.002(3) -0.010(2) C3 0.050(3) 0.032(3) 0.023(2) -0.001(2) 0.006(3) -0.017(2) C4 0.032(3) 0.024(2) 0.026(3) 0.001(2) 0.002(2) -0.002(2) C5 0.019(3) 0.023(2) 0.017(2) -0.0044(19) -0.001(2) -0.0004(18) C6 0.029(3) 0.027(2) 0.020(2) -0.0021(17) -0.002(2) 0.006(2) C7 0.018(3) 0.032(2) 0.025(3) -0.0006(19) 0.004(2) -0.0027(19) C8 0.021(3) 0.029(2) 0.017(3) 0.0029(19) -0.003(2) -0.012(2) C9 0.029(3) 0.044(3) 0.022(3) 0.002(2) 0.002(2) -0.010(2) C10 0.058(4) 0.041(3) 0.021(3) -0.001(2) 0.005(3) -0.028(3) C11 0.060(4) 0.028(3) 0.020(2) 0.001(2) 0.000(3) -0.008(2) C12 0.040(3) 0.032(2) 0.021(2) 0.002(2) -0.005(3) -0.002(2) C13 0.020(3) 0.020(2) 0.017(2) 0.0011(18) -0.0008(18) -0.0018(17) C14 0.027(3) 0.023(2) 0.0102(19) -0.0034(16) 0.0002(18) -0.0062(18) C15 0.026(3) 0.024(2) 0.022(2) 0.0018(19) 0.000(2) -0.001(2) C16 0.033(3) 0.028(3) 0.017(2) 0.001(2) 0.003(2) -0.001(2) C17 0.026(3) 0.017(2) 0.017(2) 0.0010(17) -0.0009(19) -0.0060(18) C18 0.025(3) 0.022(2) 0.025(2) -0.0014(17) 0.000(2) 0.001(2) C19 0.026(3) 0.028(3) 0.021(2) -0.0026(19) -0.006(2) 0.004(2) C20 0.029(3) 0.020(2) 0.025(2) 0.003(2) -0.002(2) 0.003(2) C21 0.030(3) 0.023(3) 0.018(2) 0.0054(18) 0.002(2) -0.005(2) C22 0.025(3) 0.020(2) 0.016(2) -0.0022(19) 0.003(2) 0.003(2) O1 0.038(2) 0.0191(17) 0.0400(19) 0.0055(14) 0.0083(16) -0.0053(15) O2 0.027(2) 0.0205(17) 0.0250(17) 0.0035(13) 0.0029(15) -0.0001(14) O3 0.029(2) 0.0270(17) 0.0410(19) 0.0045(14) 0.0045(16) 0.0060(15) N11 0.023(3) 0.032(2) 0.054(3) 0.023(2) -0.003(2) 0.0084(19) O11 0.036(2) 0.034(2) 0.035(2) -0.0025(15) 0.0013(16) 0.0061(15) O12 0.049(3) 0.050(2) 0.038(2) 0.0098(16) -0.0047(18) -0.0006(17) O13 0.052(3) 0.078(3) 0.087(3) 0.041(2) -0.017(2) 0.014(2) N21 0.028(3) 0.031(2) 0.036(2) -0.002(2) -0.001(2) -0.0004(18) O21 0.046(2) 0.075(3) 0.0268(17) 0.0111(19) 0.0032(16) 0.0046(19) O22 0.033(2) 0.060(2) 0.046(2) 0.0189(17) -0.0101(17) -0.0072(17) O23 0.028(2) 0.070(2) 0.056(2) 0.016(2) 0.0048(19) 0.0032(18) _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 Cu1 N3 1.959(3) . ? Cu1 N1 1.971(3) . ? Cu1 O11 1.972(3) . ? Cu1 N2 2.012(3) . ? N1 C1 1.312(5) . ? N1 C5 1.355(4) . ? N2 C7 1.483(5) . ? N2 C6 1.501(4) . ? N2 C13 1.505(4) . ? N3 C8 1.330(5) . ? N3 C12 1.355(4) . ? C1 C2 1.382(5) . ? C1 H1 0.9500 . ? C2 C3 1.377(6) . ? C2 H2 0.9500 . ? C3 C4 1.353(6) . ? C3 H3 0.9500 . ? C4 C5 1.392(5) . ? C4 H4 0.9500 . ? C5 C6 1.506(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.524(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.396(5) . ? C9 C10 1.383(6) . ? C9 H9 0.9500 . ? C10 C11 1.365(6) . ? C10 H10 0.9500 . ? C11 C12 1.392(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.493(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.351(5) . ? C14 C22 1.445(5) . ? C15 C16 1.437(6) . ? C15 H15 0.9500 . ? C16 O1 1.223(5) . ? C16 O2 1.368(5) . ? C17 C18 1.356(6) . ? C17 O2 1.388(4) . ? C17 C22 1.419(5) . ? C18 C19 1.400(5) . ? C18 H18 0.9500 . ? C19 O3 1.344(5) . ? C19 C20 1.394(6) . ? C20 C21 1.379(6) . ? C20 H20 0.9500 . ? C21 C22 1.417(5) . ? C21 H21 0.9500 . ? O3 H3A 0.8400 . ? N11 O13 1.223(5) . ? N11 O12 1.248(4) . ? N11 O11 1.272(4) . ? N21 O22 1.231(4) . ? N21 O23 1.233(4) . ? N21 O21 1.262(4) . ? 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 N3 Cu1 N1 166.95(14) . . ? N3 Cu1 O11 97.64(13) . . ? N1 Cu1 O11 95.33(13) . . ? N3 Cu1 N2 82.97(13) . . ? N1 Cu1 N2 84.34(13) . . ? O11 Cu1 N2 172.63(12) . . ? C1 N1 C5 119.8(3) . . ? C1 N1 Cu1 127.1(3) . . ? C5 N1 Cu1 113.1(3) . . ? C7 N2 C6 112.4(3) . . ? C7 N2 C13 107.4(3) . . ? C6 N2 C13 112.4(3) . . ? C7 N2 Cu1 106.6(2) . . ? C6 N2 Cu1 105.6(2) . . ? C13 N2 Cu1 112.4(2) . . ? C8 N3 C12 118.8(4) . . ? C8 N3 Cu1 114.7(3) . . ? C12 N3 Cu1 126.5(3) . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 117.6(4) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 119.8(4) . . ? N1 C5 C6 115.5(3) . . ? C4 C5 C6 124.7(4) . . ? N2 C6 C5 109.7(3) . . ? N2 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N2 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N2 C7 C8 108.6(3) . . ? N2 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? N2 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? N3 C8 C9 122.7(4) . . ? N3 C8 C7 115.0(3) . . ? C9 C8 C7 122.2(4) . . ? C10 C9 C8 118.0(4) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.4(4) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N3 C12 C11 121.3(5) . . ? N3 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 N2 114.1(3) . . ? C14 C13 H13A 108.7 . . ? N2 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? N2 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C22 118.2(4) . . ? C15 C14 C13 119.6(4) . . ? C22 C14 C13 122.1(3) . . ? C14 C15 C16 123.2(4) . . ? C14 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? O1 C16 O2 116.9(4) . . ? O1 C16 C15 125.8(4) . . ? O2 C16 C15 117.3(4) . . ? C18 C17 O2 116.7(4) . . ? C18 C17 C22 123.5(4) . . ? O2 C17 C22 119.8(4) . . ? C17 C18 C19 119.5(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? O3 C19 C20 118.0(4) . . ? O3 C19 C18 122.8(4) . . ? C20 C19 C18 119.1(4) . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 121.1(4) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C21 C22 C17 115.8(4) . . ? C21 C22 C14 125.3(4) . . ? C17 C22 C14 118.9(3) . . ? C16 O2 C17 122.3(3) . . ? C19 O3 H3A 109.5 . . ? O13 N11 O12 122.0(4) . . ? O13 N11 O11 120.6(4) . . ? O12 N11 O11 117.4(4) . . ? N11 O11 Cu1 104.4(3) . . ? O22 N21 O23 121.0(4) . . ? O22 N21 O21 119.6(4) . . ? O23 N21 O21 119.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C1 -176.4(5) . . . . ? O11 Cu1 N1 C1 9.6(4) . . . . ? N2 Cu1 N1 C1 -163.0(4) . . . . ? N3 Cu1 N1 C5 1.4(8) . . . . ? O11 Cu1 N1 C5 -172.6(3) . . . . ? N2 Cu1 N1 C5 14.7(3) . . . . ? N3 Cu1 N2 C7 29.3(2) . . . . ? N1 Cu1 N2 C7 -147.7(2) . . . . ? N3 Cu1 N2 C6 149.0(2) . . . . ? N3 Cu1 N2 C13 -88.1(2) . . . . ? N1 Cu1 N2 C13 94.9(2) . . . . ? N1 Cu1 N3 C8 -3.1(8) . . . . ? O11 Cu1 N3 C8 170.9(3) . . . . ? N2 Cu1 N3 C8 -16.5(3) . . . . ? N1 Cu1 N3 C12 179.4(5) . . . . ? O11 Cu1 N3 C12 -6.6(4) . . . . ? N2 Cu1 N3 C12 166.0(4) . . . . ? C5 N1 C1 C2 -0.3(7) . . . . ? Cu1 N1 C1 C2 177.4(3) . . . . ? N1 C1 C2 C3 1.2(7) . . . . ? C1 C2 C3 C4 -1.6(7) . . . . ? C2 C3 C4 C5 1.2(8) . . . . ? C1 N1 C5 C4 -0.2(7) . . . . ? Cu1 N1 C5 C4 -178.2(3) . . . . ? C1 N1 C5 C6 -178.8(4) . . . . ? Cu1 N1 C5 C6 3.2(5) . . . . ? C3 C4 C5 N1 -0.2(7) . . . . ? C3 C4 C5 C6 178.3(4) . . . . ? C7 N2 C6 C5 151.8(3) . . . . ? C13 N2 C6 C5 -86.9(4) . . . . ? Cu1 N2 C6 C5 36.0(3) . . . . ? N1 C5 C6 N2 -27.1(5) . . . . ? C4 C5 C6 N2 154.4(4) . . . . ? C6 N2 C7 C8 -151.4(3) . . . . ? C13 N2 C7 C8 84.4(4) . . . . ? Cu1 N2 C7 C8 -36.2(3) . . . . ? C12 N3 C8 C9 -0.8(6) . . . . ? Cu1 N3 C8 C9 -178.5(3) . . . . ? C12 N3 C8 C7 176.7(4) . . . . ? Cu1 N3 C8 C7 -1.0(5) . . . . ? N2 C7 C8 N3 25.6(5) . . . . ? N2 C7 C8 C9 -156.9(3) . . . . ? N3 C8 C9 C10 0.4(6) . . . . ? C7 C8 C9 C10 -176.9(4) . . . . ? C8 C9 C10 C11 0.2(7) . . . . ? C9 C10 C11 C12 -0.5(7) . . . . ? C8 N3 C12 C11 0.4(7) . . . . ? Cu1 N3 C12 C11 177.9(3) . . . . ? C10 C11 C12 N3 0.2(7) . . . . ? C7 N2 C13 C14 177.2(3) . . . . ? C6 N2 C13 C14 53.1(4) . . . . ? Cu1 N2 C13 C14 -65.9(4) . . . . ? N2 C13 C14 C15 -96.2(4) . . . . ? N2 C13 C14 C22 80.8(4) . . . . ? C22 C14 C15 C16 -6.9(6) . . . . ? C13 C14 C15 C16 170.2(4) . . . . ? C14 C15 C16 O1 -173.0(4) . . . . ? C14 C15 C16 O2 6.2(6) . . . . ? O2 C17 C18 C19 179.6(3) . . . . ? C22 C17 C18 C19 -0.8(6) . . . . ? C17 C18 C19 O3 177.8(3) . . . . ? C17 C18 C19 C20 -0.7(6) . . . . ? O3 C19 C20 C21 -176.3(4) . . . . ? C18 C19 C20 C21 2.2(6) . . . . ? C19 C20 C21 C22 -2.3(6) . . . . ? C20 C21 C22 C17 0.9(6) . . . . ? C20 C21 C22 C14 -178.6(4) . . . . ? C18 C17 C22 C21 0.7(6) . . . . ? O2 C17 C22 C21 -179.7(3) . . . . ? C18 C17 C22 C14 -179.8(4) . . . . ? O2 C17 C22 C14 -0.2(5) . . . . ? C15 C14 C22 C21 -176.7(4) . . . . ? C13 C14 C22 C21 6.2(6) . . . . ? C15 C14 C22 C17 3.8(5) . . . . ? C13 C14 C22 C17 -173.2(3) . . . . ? O1 C16 O2 C17 177.0(3) . . . . ? C15 C16 O2 C17 -2.2(5) . . . . ? C18 C17 O2 C16 179.1(3) . . . . ? C22 C17 O2 C16 -0.5(5) . . . . ? O13 N11 O11 Cu1 -174.3(4) . . . . ? O12 N11 O11 Cu1 3.3(4) . . . . ? N3 Cu1 O11 N11 -92.7(3) . . . . ? N1 Cu1 O11 N11 85.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.403 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.129