# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email 'linhongyan 2005@126.com' _publ_contact_author_name 'Hong-Yan Lin' loop_ _publ_author_name 'Xiuli Wang' 'Hongyan Lin' 'Bao Mu' 'Aixiang Tian' 'Guocheng Liu' data_compd1 _database_code_depnum_ccdc_archive 'CCDC 768202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 Cu2 N4 O16' _chemical_formula_weight 855.70 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.3152(16) _cell_length_b 18.995(2) _cell_length_c 12.6405(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3437.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2554 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 25.05 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 1.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7169 _exptl_absorpt_correction_T_max 0.8904 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16658 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.18 _reflns_number_total 3181 _reflns_number_gt 2124 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0541P)^2^+4.9471P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3181 _refine_ls_number_parameters 256 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1163 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.026 _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 0.13152(3) 0.52565(2) 0.88363(4) 0.02496(17) Uani 1 1 d . . . O1W O -0.0046(2) 0.54405(14) 0.8833(2) 0.0314(7) Uani 1 1 d . . . H1A H -0.0437 0.5127 0.8779 0.038 Uiso 1 1 d R . . H1B H -0.0202 0.5701 0.9319 0.038 Uiso 1 1 d R . . O2W O 0.3353(3) 0.6760(2) 0.8799(4) 0.0816(14) Uani 1 1 d . . . H2A H 0.2856 0.6550 0.8871 0.098 Uiso 1 1 d R . . O3W O 0.3464(4) 0.6806(3) 0.6571(5) 0.149(3) Uani 1 1 d . . . H3A H 0.3385 0.6607 0.6004 0.179 Uiso 1 1 d R . . O1 O 0.1076(2) 0.43736(14) 0.8118(2) 0.0332(7) Uani 1 1 d . . . O2 O 0.0834(2) 0.38029(15) 0.9639(2) 0.0394(8) Uani 1 1 d . . . O3 O 0.1526(2) 0.61697(14) 0.9506(2) 0.0300(7) Uani 1 1 d . . . O4 O 0.1253(2) 0.56343(14) 1.1042(2) 0.0352(7) Uani 1 1 d . . . O5 O 0.1551(2) 0.57932(16) 0.7222(2) 0.0392(8) Uani 1 1 d . . . N1 N 0.2376(2) 0.50692(17) 0.4186(3) 0.0264(8) Uani 1 1 d . . . N2 N 0.1035(4) 0.6771(2) 0.6394(3) 0.0605(14) Uani 1 1 d D . . C1 C 0.0941(3) 0.3817(2) 0.8661(3) 0.0283(10) Uani 1 1 d . . . C2 C 0.0949(3) 0.3139(2) 0.8053(3) 0.0251(9) Uani 1 1 d . . . C3 C 0.1071(3) 0.3133(2) 0.6964(3) 0.0280(10) Uani 1 1 d . . . H3 H 0.1120 0.3555 0.6596 0.034 Uiso 1 1 calc R . . C4 C 0.1122(4) 0.2500 0.6423(5) 0.0337(15) Uani 1 2 d S . . H4 H 0.1190 0.2500 0.5691 0.040 Uiso 1 2 calc SR . . C5 C 0.0882(4) 0.2500 0.8592(4) 0.0239(13) Uani 1 2 d S . . H5 H 0.0791 0.2500 0.9320 0.029 Uiso 1 2 calc SR . . C6 C 0.1413(3) 0.6172(2) 1.0516(3) 0.0262(9) Uani 1 1 d . . . C7 C 0.1494(3) 0.6864(2) 1.1064(3) 0.0243(9) Uani 1 1 d . . . C8 C 0.1609(3) 0.6871(2) 1.2156(3) 0.0312(10) Uani 1 1 d . . . H8 H 0.1632 0.6449 1.2526 0.037 Uiso 1 1 calc R . . C9 C 0.1691(5) 0.7500 1.2697(5) 0.0361(16) Uani 1 2 d S . . H9 H 0.1800 0.7500 1.3422 0.043 Uiso 1 2 calc SR . . C10 C 0.1455(4) 0.7500 1.0514(4) 0.0240(13) Uani 1 2 d S . . H10 H 0.1403 0.7500 0.9781 0.029 Uiso 1 2 calc SR . . C11 C 0.2225(3) 0.5406(2) 0.5104(3) 0.0282(10) Uani 1 1 d . . . H11 H 0.2710 0.5428 0.5593 0.034 Uiso 1 1 calc R . . C12 C 0.1388(3) 0.5719(2) 0.5359(3) 0.0255(9) Uani 1 1 d . . . C13 C 0.0658(3) 0.5651(2) 0.4650(3) 0.0334(10) Uani 1 1 d . . . H13 H 0.0077 0.5845 0.4804 0.040 Uiso 1 1 calc R . . C14 C 0.0792(3) 0.5295(2) 0.3716(3) 0.0365(11) Uani 1 1 d . . . H14 H 0.0305 0.5243 0.3236 0.044 Uiso 1 1 calc R . . C15 C 0.1662(3) 0.5017(2) 0.3505(4) 0.0342(11) Uani 1 1 d . . . H15 H 0.1757 0.4785 0.2866 0.041 Uiso 1 1 calc R . . C16 C 0.1321(3) 0.6100(2) 0.6409(3) 0.0290(10) Uani 1 1 d . . . C17A C 0.0660(7) 0.7152(4) 0.5467(6) 0.0359(17) Uani 0.50 1 d PD . 1 H17A H 0.1011 0.6999 0.4852 0.043 Uiso 0.50 1 calc PR . 1 H17B H 0.0020 0.6999 0.5365 0.043 Uiso 0.50 1 calc PR . 1 C18A C 0.0696(7) 0.7123(5) 0.7352(6) 0.0338(18) Uani 0.50 1 d PD . 1 H18A H 0.0062 0.6965 0.7482 0.041 Uiso 0.50 1 calc PR . 1 H18B H 0.1074 0.6965 0.7942 0.041 Uiso 0.50 1 calc PR . 1 C17B C 0.1331(7) 0.7232(4) 0.5469(6) 0.0359(17) Uani 0.50 1 d PD . 2 H17C H 0.1964 0.7091 0.5295 0.043 Uiso 0.50 1 calc PR . 2 H17D H 0.0944 0.7091 0.4876 0.043 Uiso 0.50 1 calc PR . 2 C18B C 0.1299(7) 0.7218(5) 0.7359(6) 0.0338(18) Uani 0.50 1 d PD . 2 H18C H 0.0887 0.7074 0.7928 0.041 Uiso 0.50 1 calc PR . 2 H18D H 0.1923 0.7074 0.7563 0.041 Uiso 0.50 1 calc PR . 2 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 0.0367(3) 0.0158(2) 0.0224(3) -0.0003(2) -0.0017(2) 0.0011(2) O1W 0.0368(16) 0.0230(15) 0.0345(17) -0.0061(13) 0.0002(14) -0.0007(12) O2W 0.067(3) 0.061(3) 0.117(4) -0.007(3) 0.023(3) -0.015(2) O3W 0.148(5) 0.161(6) 0.140(5) -0.092(5) 0.079(4) -0.030(4) O1 0.0494(19) 0.0159(15) 0.0344(18) -0.0023(13) -0.0035(14) 0.0001(13) O2 0.064(2) 0.0293(17) 0.0250(18) -0.0062(13) 0.0059(15) 0.0080(16) O3 0.0449(19) 0.0204(15) 0.0246(17) -0.0032(12) -0.0012(13) 0.0001(13) O4 0.0501(19) 0.0209(15) 0.0348(18) 0.0058(13) -0.0009(15) -0.0059(14) O5 0.062(2) 0.0334(17) 0.0227(17) 0.0067(14) 0.0051(14) 0.0113(16) N1 0.038(2) 0.0201(18) 0.0215(18) -0.0017(14) 0.0007(15) 0.0025(15) N2 0.136(4) 0.031(2) 0.014(2) 0.0020(16) 0.007(2) 0.034(3) C1 0.031(2) 0.019(2) 0.035(3) -0.0025(18) -0.0003(19) 0.0036(18) C2 0.028(2) 0.019(2) 0.028(2) -0.0025(17) 0.0010(18) 0.0008(18) C3 0.035(3) 0.021(2) 0.028(2) 0.0042(18) -0.0013(19) 0.0015(19) C4 0.042(4) 0.032(3) 0.027(4) 0.000 -0.002(3) 0.000 C5 0.031(3) 0.022(3) 0.018(3) 0.000 0.007(2) 0.000 C6 0.024(2) 0.025(2) 0.029(3) 0.0003(18) -0.0016(18) 0.0017(19) C7 0.026(2) 0.023(2) 0.024(2) 0.0011(17) 0.0036(17) -0.0016(17) C8 0.044(3) 0.025(2) 0.024(2) 0.0044(19) 0.005(2) -0.003(2) C9 0.058(4) 0.036(4) 0.015(3) 0.000 0.001(3) 0.000 C10 0.032(3) 0.023(3) 0.018(3) 0.000 0.000(2) 0.000 C11 0.038(2) 0.024(2) 0.023(2) 0.0009(17) -0.0025(19) -0.0008(19) C12 0.037(2) 0.016(2) 0.023(2) 0.0038(16) 0.0055(19) 0.0003(19) C13 0.036(3) 0.032(3) 0.032(3) 0.007(2) 0.003(2) 0.001(2) C14 0.039(3) 0.038(3) 0.033(3) 0.000(2) -0.004(2) -0.004(2) C15 0.053(3) 0.026(2) 0.024(3) -0.0009(18) 0.000(2) -0.005(2) C16 0.040(2) 0.027(2) 0.020(2) 0.0035(17) 0.0076(19) 0.004(2) C17A 0.061(5) 0.027(3) 0.019(3) 0.002(2) -0.007(4) 0.000(4) C18A 0.052(5) 0.036(3) 0.013(3) 0.005(2) 0.011(4) 0.008(4) C17B 0.061(5) 0.027(3) 0.019(3) 0.002(2) -0.007(4) 0.000(4) C18B 0.052(5) 0.036(3) 0.013(3) 0.005(2) 0.011(4) 0.008(4) _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 O1 1.937(3) . ? Cu1 O3 1.953(3) . ? Cu1 O1W 1.979(3) . ? Cu1 N1 2.021(4) 2_565 ? Cu1 O5 2.306(3) . ? O1W H1A 0.8203 . ? O1W H1B 0.8190 . ? O2W H2A 0.8201 . ? O3W H3A 0.8186 . ? O1 C1 1.275(5) . ? O2 C1 1.246(5) . ? O3 C6 1.287(5) . ? O4 C6 1.240(5) . ? O5 C16 1.226(5) . ? N1 C15 1.340(6) . ? N1 C11 1.344(5) . ? N1 Cu1 2.021(4) 2_564 ? N2 C16 1.340(5) . ? N2 C17A 1.478(7) . ? N2 C18A 1.465(7) . ? N2 C17B 1.521(7) . ? N2 C18B 1.533(7) . ? C1 C2 1.500(5) . ? C2 C3 1.388(6) . ? C2 C5 1.395(5) . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C3 1.385(5) 7_565 ? C4 H4 0.9300 . ? C5 C2 1.395(5) 7_565 ? C5 H5 0.9300 . ? C6 C7 1.490(5) . ? C7 C8 1.389(5) . ? C7 C10 1.395(5) . ? C8 C9 1.381(5) . ? C8 H8 0.9300 . ? C9 C8 1.381(5) 7_575 ? C9 H9 0.9300 . ? C10 C7 1.395(5) 7_575 ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 C13 1.383(6) . ? C12 C16 1.514(5) . ? C13 C14 1.373(6) . ? C13 H13 0.9300 . ? C14 C15 1.379(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17A C17A 1.321(17) 7_575 ? C17A H17A 0.9700 . ? C17A H17B 0.9700 . ? C18A C18A 1.431(18) 7_575 ? C18A H18A 0.9700 . ? C18A H18B 0.9700 . ? C17B C17B 1.018(16) 7_575 ? C17B H17C 0.9700 . ? C17B H17D 0.9700 . ? C18B C18B 1.071(17) 7_575 ? C18B H18C 0.9700 . ? C18B H18D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 177.28(12) . . ? O1 Cu1 O1W 88.76(12) . . ? O3 Cu1 O1W 89.75(12) . . ? O1 Cu1 N1 90.06(13) . 2_565 ? O3 Cu1 N1 91.96(13) . 2_565 ? O1W Cu1 N1 165.13(13) . 2_565 ? O1 Cu1 O5 89.63(12) . . ? O3 Cu1 O5 88.18(11) . . ? O1W Cu1 O5 93.67(11) . . ? N1 Cu1 O5 101.14(12) 2_565 . ? Cu1 O1W H1A 122.9 . . ? Cu1 O1W H1B 112.0 . . ? H1A O1W H1B 108.3 . . ? C1 O1 Cu1 119.5(3) . . ? C6 O3 Cu1 114.5(3) . . ? C16 O5 Cu1 155.9(3) . . ? C15 N1 C11 117.8(4) . . ? C15 N1 Cu1 123.0(3) . 2_564 ? C11 N1 Cu1 118.9(3) . 2_564 ? C16 N2 C17A 126.0(5) . . ? C16 N2 C18A 121.6(5) . . ? C17A N2 C18A 108.1(6) . . ? C16 N2 C17B 118.2(5) . . ? C16 N2 C18B 116.2(5) . . ? C17B N2 C18B 102.9(5) . . ? O2 C1 O1 124.8(4) . . ? O2 C1 C2 119.4(4) . . ? O1 C1 C2 115.8(4) . . ? C3 C2 C5 119.1(4) . . ? C3 C2 C1 121.1(4) . . ? C5 C2 C1 119.8(4) . . ? C4 C3 C2 120.2(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C3 120.4(6) 7_565 . ? C3 C4 H4 119.8 7_565 . ? C3 C4 H4 119.8 . . ? C2 C5 C2 120.9(5) 7_565 . ? C2 C5 H5 119.5 7_565 . ? C2 C5 H5 119.5 . . ? O4 C6 O3 123.4(4) . . ? O4 C6 C7 119.5(4) . . ? O3 C6 C7 117.1(4) . . ? C8 C7 C10 119.4(4) . . ? C8 C7 C6 118.7(4) . . ? C10 C7 C6 121.9(4) . . ? C7 C8 C9 120.7(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C8 119.7(6) 7_575 . ? C8 C9 H9 120.2 7_575 . ? C8 C9 H9 120.2 . . ? C7 C10 C7 119.9(5) 7_575 . ? C7 C10 H10 120.0 7_575 . ? C7 C10 H10 120.0 . . ? N1 C11 C12 123.3(4) . . ? N1 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C11 C12 C13 117.8(4) . . ? C11 C12 C16 117.8(4) . . ? C13 C12 C16 124.4(4) . . ? C14 C13 C12 119.8(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 118.8(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? N1 C15 C14 122.4(4) . . ? N1 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? O5 C16 N2 123.0(4) . . ? O5 C16 C12 119.4(4) . . ? N2 C16 C12 117.5(3) . . ? C17A C17A N2 119.3(4) 7_575 . ? C17A C17A H17A 107.5 7_575 . ? N2 C17A H17A 107.5 . . ? C17A C17A H17B 107.5 7_575 . ? N2 C17A H17B 107.5 . . ? H17A C17A H17B 107.0 . . ? C18A C18A N2 117.2(4) 7_575 . ? C18A C18A H18A 108.0 7_575 . ? N2 C18A H18A 108.0 . . ? C18A C18A H18B 108.0 7_575 . ? N2 C18A H18B 108.0 . . ? H18A C18A H18B 107.3 . . ? C17B C17B N2 125.1(4) 7_575 . ? C17B C17B H17C 106.0 7_575 . ? N2 C17B H17C 106.0 . . ? C17B C17B H17D 106.0 7_575 . ? N2 C17B H17D 106.0 . . ? H17C C17B H17D 106.3 . . ? C18B C18B N2 123.6(4) 7_575 . ? C18B C18B H18C 106.4 7_575 . ? N2 C18B H18C 106.4 . . ? C18B C18B H18D 106.4 7_575 . ? N2 C18B H18D 106.4 . . ? H18C C18B H18D 106.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1W Cu1 O1 C1 -90.6(3) . . . . ? N1 Cu1 O1 C1 74.6(3) 2_565 . . . ? O5 Cu1 O1 C1 175.7(3) . . . . ? O1W Cu1 O3 C6 82.4(3) . . . . ? N1 Cu1 O3 C6 -82.8(3) 2_565 . . . ? O5 Cu1 O3 C6 176.1(3) . . . . ? O1 Cu1 O5 C16 86.7(7) . . . . ? O3 Cu1 O5 C16 -91.7(7) . . . . ? O1W Cu1 O5 C16 -2.0(7) . . . . ? N1 Cu1 O5 C16 176.7(7) 2_565 . . . ? Cu1 O1 C1 O2 9.4(6) . . . . ? Cu1 O1 C1 C2 -168.5(3) . . . . ? O2 C1 C2 C3 -179.7(4) . . . . ? O1 C1 C2 C3 -1.7(6) . . . . ? O2 C1 C2 C5 -3.1(7) . . . . ? O1 C1 C2 C5 174.9(4) . . . . ? C5 C2 C3 C4 0.3(7) . . . . ? C1 C2 C3 C4 176.9(4) . . . . ? C2 C3 C4 C3 -1.5(9) . . . 7_565 ? C3 C2 C5 C2 0.9(9) . . . 7_565 ? C1 C2 C5 C2 -175.7(3) . . . 7_565 ? Cu1 O3 C6 O4 5.1(5) . . . . ? Cu1 O3 C6 C7 -175.6(3) . . . . ? O4 C6 C7 C8 15.1(6) . . . . ? O3 C6 C7 C8 -164.2(4) . . . . ? O4 C6 C7 C10 -164.7(4) . . . . ? O3 C6 C7 C10 15.9(6) . . . . ? C10 C7 C8 C9 -0.4(7) . . . . ? C6 C7 C8 C9 179.7(5) . . . . ? C7 C8 C9 C8 3.3(10) . . . 7_575 ? C8 C7 C10 C7 -2.6(8) . . . 7_575 ? C6 C7 C10 C7 177.3(3) . . . 7_575 ? C15 N1 C11 C12 -2.5(6) . . . . ? Cu1 N1 C11 C12 172.1(3) 2_564 . . . ? N1 C11 C12 C13 3.3(6) . . . . ? N1 C11 C12 C16 -178.3(4) . . . . ? C11 C12 C13 C14 -1.7(6) . . . . ? C16 C12 C13 C14 180.0(4) . . . . ? C12 C13 C14 C15 -0.5(6) . . . . ? C11 N1 C15 C14 0.1(6) . . . . ? Cu1 N1 C15 C14 -174.3(3) 2_564 . . . ? C13 C14 C15 N1 1.4(7) . . . . ? Cu1 O5 C16 N2 71.4(9) . . . . ? Cu1 O5 C16 C12 -110.7(7) . . . . ? C17A N2 C16 O5 -173.6(7) . . . . ? C18A N2 C16 O5 -19.5(9) . . . . ? C17B N2 C16 O5 142.4(6) . . . . ? C18B N2 C16 O5 19.2(8) . . . . ? C17A N2 C16 C12 8.5(9) . . . . ? C18A N2 C16 C12 162.6(6) . . . . ? C17B N2 C16 C12 -35.6(7) . . . . ? C18B N2 C16 C12 -158.7(5) . . . . ? C11 C12 C16 O5 -52.2(6) . . . . ? C13 C12 C16 O5 126.1(5) . . . . ? C11 C12 C16 N2 125.9(5) . . . . ? C13 C12 C16 N2 -55.8(6) . . . . ? C16 N2 C17A C17A -160.3(4) . . . 7_575 ? C18A N2 C17A C17A 42.7(7) . . . 7_575 ? C17B N2 C17A C17A -69.3(8) . . . 7_575 ? C18B N2 C17A C17A 6.8(7) . . . 7_575 ? C16 N2 C18A C18A 160.2(4) . . . 7_575 ? C17A N2 C18A C18A -41.7(7) . . . 7_575 ? C17B N2 C18A C18A -1.8(7) . . . 7_575 ? C18B N2 C18A C18A 69.4(9) . . . 7_575 ? C16 N2 C17B C17B -160.7(3) . . . 7_575 ? C17A N2 C17B C17B 86.0(9) . . . 7_575 ? C18A N2 C17B C17B 1.9(8) . . . 7_575 ? C18B N2 C17B C17B -31.1(6) . . . 7_575 ? C16 N2 C18B C18B 161.3(3) . . . 7_575 ? C17A N2 C18B C18B -7.1(8) . . . 7_575 ? C18A N2 C18B C18B -90.2(10) . . . 7_575 ? C17B N2 C18B C18B 30.5(6) . . . 7_575 ? 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 O1W H1A O4 0.82 1.87 2.679(4) 168 5_567 O1W H1B O2 0.82 1.86 2.659(4) 166 5_567 O2W H2A O3 0.82 2.19 2.983(5) 163 . O3W H3A O2 0.82 2.20 2.883(6) 141 2_564 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.18 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.584 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.080 ####END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 768204' #TrackingRef '- compounds 1-3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 Cu N4 O9' _chemical_formula_sum 'C25 H22 Cu N4 O9' _chemical_formula_weight 586.01 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8482(11) _cell_length_b 20.186(2) _cell_length_c 16.4951(15) _cell_angle_alpha 90.00 _cell_angle_beta 123.748(5) _cell_angle_gamma 90.00 _cell_volume 2726.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 0.859 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13566 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4802 _reflns_number_gt 3314 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+2.1999P] 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 4802 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Cu1 Cu -0.15138(6) -0.62283(2) 0.65916(4) 0.0310(2) Uani 1 1 d . . . O1 O 0.1687(7) -0.7472(3) 1.0660(4) 0.148(3) Uani 1 1 d . . . O2 O 0.5910(5) -0.4700(2) 1.2878(3) 0.0803(14) Uani 1 1 d . . . O3 O -0.1926(4) -0.78518(16) 0.6260(3) 0.0581(11) Uani 1 1 d . . . O4 O 0.0235(4) -0.51365(16) 0.7658(3) 0.0616(11) Uani 1 1 d . . . O5 O -0.4196(4) -0.65280(15) 0.5548(2) 0.0425(8) Uani 1 1 d . . . O6 O -0.2334(4) -0.53324(13) 0.6479(2) 0.0372(8) Uani 1 1 d . . . O7 O -0.0164(4) -0.70141(13) 0.6923(2) 0.0380(8) Uani 1 1 d . . . O8 O -0.4595(5) -0.74885(18) 0.4799(3) 0.0690(15) Uani 1 1 d . . . N1 N 0.2888(6) -0.6532(2) 1.0726(4) 0.0805(17) Uani 1 1 d . . . N2 N 0.4929(7) -0.5709(2) 1.2301(3) 0.0800(17) Uani 1 1 d . . . N3 N 0.8721(4) -0.60217(18) 1.5478(3) 0.0353(9) Uani 1 1 d . . . N4 N -0.1516(5) -0.64012(18) 0.7784(3) 0.0389(9) Uani 1 1 d . . . C1 C 0.4917(11) -0.6441(4) 1.2415(5) 0.102(3) Uani 1 1 d . . . H1A H 0.5988 -0.6587 1.2948 0.123 Uiso 1 1 calc R . . H1B H 0.4136 -0.6555 1.2576 0.123 Uiso 1 1 calc R . . C2 C 0.4494(9) -0.6772(4) 1.1545(5) 0.098(3) Uani 1 1 d . . . H2A H 0.4447 -0.7246 1.1622 0.118 Uiso 1 1 calc R . . H2B H 0.5318 -0.6687 1.1408 0.118 Uiso 1 1 calc R . . C3 C 1.0229(8) -0.6013(4) 1.4758(5) 0.078(2) Uani 1 1 d . . . H3A H 1.1201 -0.6105 1.4812 0.093 Uiso 1 1 calc R . . C4 C 0.1607(8) -0.6921(3) 1.0353(4) 0.0722(19) Uani 1 1 d . . . C5 C 0.3377(8) -0.5470(3) 1.1444(4) 0.089(2) Uani 1 1 d . . . H5A H 0.2532 -0.5510 1.1573 0.107 Uiso 1 1 calc R . . H5B H 0.3489 -0.5004 1.1351 0.107 Uiso 1 1 calc R . . C6 C -0.1426(10) -0.6705(4) 0.9444(5) 0.096(2) Uani 1 1 d . . . H6A H -0.1396 -0.6811 1.0002 0.115 Uiso 1 1 calc R . . C7 C -0.2875(7) -0.6399(3) 0.7777(4) 0.0615(16) Uani 1 1 d . . . H7A H -0.3855 -0.6287 0.7203 0.074 Uiso 1 1 calc R . . C8 C -0.2889(9) -0.6556(4) 0.8593(5) 0.094(2) Uani 1 1 d . . . H8A H -0.3860 -0.6561 0.8564 0.112 Uiso 1 1 calc R . . C9 C 0.8932(8) -0.5731(3) 1.3920(4) 0.0707(18) Uani 1 1 d . . . H9A H 0.9016 -0.5628 1.3400 0.085 Uiso 1 1 calc R . . C10 C 0.0023(7) -0.6696(3) 0.9471(4) 0.0568(15) Uani 1 1 d . . . C11 C 0.2879(9) -0.5811(3) 1.0583(5) 0.090(2) Uani 1 1 d . . . H11A H 0.3608 -0.5705 1.0379 0.108 Uiso 1 1 calc R . . H11B H 0.1787 -0.5671 1.0071 0.108 Uiso 1 1 calc R . . C12 C 1.0059(7) -0.6156(3) 1.5510(4) 0.0558(15) Uani 1 1 d . . . H12A H 1.0926 -0.6356 1.6067 0.067 Uiso 1 1 calc R . . C13 C 0.6053(7) -0.5292(3) 1.2970(4) 0.0505(13) Uani 1 1 d . . . C14 C 0.7529(6) -0.5604(2) 1.3867(3) 0.0445(12) Uani 1 1 d . . . C15 C -0.0096(6) -0.6537(2) 0.8625(3) 0.0429(12) Uani 1 1 d . . . H15A H 0.0857 -0.6523 0.8636 0.051 Uiso 1 1 calc R . . C16 C -0.0562(5) -0.7613(2) 0.6844(3) 0.0345(11) Uani 1 1 d . . . C17 C 0.7483(6) -0.5743(2) 1.4670(3) 0.0391(11) Uani 1 1 d . . . H17A H 0.6543 -0.5638 1.4646 0.047 Uiso 1 1 calc R . . C18 C 0.0755(5) -0.8093(2) 0.7531(3) 0.0295(10) Uani 1 1 d . . . C19 C -0.1577(5) -0.42239(19) 0.6929(3) 0.0286(10) Uani 1 1 d . . . C20 C 0.2250(5) -0.7872(2) 0.8314(3) 0.0310(10) Uani 1 1 d . . . H20A H 0.2496 -0.7422 0.8390 0.037 Uiso 1 1 calc R . . C21 C -0.1166(5) -0.4950(2) 0.7053(3) 0.0342(11) Uani 1 1 d . . . C22 C -0.3024(5) -0.3997(2) 0.6130(3) 0.0299(10) Uani 1 1 d . . . H22A H -0.3769 -0.4296 0.5665 0.036 Uiso 1 1 calc R . . C23 C 0.3378(5) -0.83230(19) 0.8985(3) 0.0288(10) Uani 1 1 d . . . C24 C 0.0428(5) -0.87683(19) 0.7410(3) 0.0303(10) Uani 1 1 d . . . H24A H -0.0571 -0.8918 0.6883 0.036 Uiso 1 1 calc R . . C25 C -0.5029(5) -0.6893(2) 0.4861(3) 0.0345(11) Uani 1 1 d . . . O1W O 0.6780(11) -0.4196(6) 1.1498(7) 0.278(7) Uani 1 1 d . . . H1WA H 0.7752 -0.4341 1.1854 0.334 Uiso 1 1 d R . . H1WB H 0.6561 -0.4289 1.1917 0.334 Uiso 1 1 d R . . H8B H -0.376(7) -0.755(3) 0.519(4) 0.07(2) 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 Cu1 0.0329(3) 0.0186(3) 0.0246(3) 0.0024(2) 0.0055(2) 0.0024(2) O1 0.138(5) 0.090(4) 0.087(4) 0.046(3) -0.018(3) -0.048(4) O2 0.080(3) 0.051(3) 0.059(3) 0.008(2) 0.007(2) 0.007(2) O3 0.0315(18) 0.0358(19) 0.053(2) 0.0051(16) -0.0098(16) 0.0061(15) O4 0.0300(19) 0.0310(19) 0.079(3) 0.0072(18) 0.0021(19) 0.0072(14) O5 0.0321(17) 0.0325(17) 0.0341(18) -0.0059(14) 0.0005(15) -0.0012(13) O6 0.0403(18) 0.0182(15) 0.0369(17) -0.0017(13) 0.0113(15) -0.0026(13) O7 0.0382(18) 0.0240(16) 0.0380(18) 0.0096(13) 0.0126(15) 0.0081(13) O8 0.042(2) 0.039(2) 0.054(2) -0.0137(18) -0.018(2) 0.0180(17) N1 0.072(4) 0.050(3) 0.063(3) 0.011(3) 0.002(3) 0.000(3) N2 0.091(4) 0.047(3) 0.042(3) 0.007(2) -0.001(3) 0.010(3) N3 0.031(2) 0.0295(19) 0.033(2) 0.0028(16) 0.0097(17) 0.0042(16) N4 0.042(2) 0.031(2) 0.033(2) 0.0019(16) 0.0146(19) -0.0018(16) C1 0.128(7) 0.067(5) 0.049(4) 0.007(3) 0.010(4) 0.012(4) C2 0.098(6) 0.067(5) 0.069(5) -0.002(4) 0.009(4) 0.016(4) C3 0.063(4) 0.109(5) 0.076(5) 0.035(4) 0.048(4) 0.031(4) C4 0.085(5) 0.066(4) 0.029(3) 0.010(3) 0.010(3) -0.017(3) C5 0.088(5) 0.067(4) 0.049(4) 0.013(3) -0.001(4) 0.016(4) C6 0.107(6) 0.125(7) 0.051(4) 0.020(4) 0.042(4) -0.009(5) C7 0.054(4) 0.076(4) 0.044(3) -0.001(3) 0.020(3) -0.001(3) C8 0.075(5) 0.155(8) 0.060(4) 0.011(5) 0.043(4) -0.006(5) C9 0.075(4) 0.094(5) 0.058(4) 0.023(4) 0.045(4) 0.020(4) C10 0.064(4) 0.059(4) 0.035(3) 0.002(2) 0.020(3) -0.012(3) C11 0.084(5) 0.067(4) 0.060(4) 0.009(4) 0.004(4) -0.009(4) C12 0.047(3) 0.059(4) 0.050(3) 0.020(3) 0.021(3) 0.014(3) C13 0.057(3) 0.053(3) 0.030(3) 0.007(2) 0.017(2) -0.001(3) C14 0.045(3) 0.042(3) 0.039(3) 0.006(2) 0.019(2) 0.000(2) C15 0.047(3) 0.034(3) 0.030(3) 0.000(2) 0.011(2) -0.008(2) C16 0.034(3) 0.029(2) 0.025(2) 0.0028(18) 0.006(2) 0.0043(19) C17 0.035(3) 0.038(3) 0.036(3) 0.005(2) 0.015(2) 0.000(2) C18 0.023(2) 0.025(2) 0.027(2) 0.0057(17) 0.0060(18) 0.0051(16) C19 0.028(2) 0.020(2) 0.028(2) -0.0006(17) 0.0090(19) -0.0004(16) C20 0.030(2) 0.020(2) 0.031(2) 0.0008(17) 0.009(2) -0.0027(17) C21 0.034(3) 0.021(2) 0.041(3) 0.0003(19) 0.017(2) 0.0001(19) C22 0.026(2) 0.024(2) 0.031(2) -0.0072(18) 0.010(2) -0.0066(17) C23 0.023(2) 0.022(2) 0.028(2) 0.0011(17) 0.0058(18) 0.0007(16) C24 0.022(2) 0.027(2) 0.028(2) -0.0009(18) 0.0050(18) -0.0006(17) C25 0.027(2) 0.023(2) 0.037(3) -0.0027(19) 0.007(2) -0.0012(18) O1W 0.163(8) 0.453(18) 0.251(11) 0.206(12) 0.136(8) 0.154(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.943(3) . ? Cu1 O6 1.947(3) . ? Cu1 N4 1.999(4) . ? Cu1 N3 2.018(4) 1_454 ? Cu1 O5 2.292(3) . ? O1 C4 1.205(7) . ? O2 C13 1.204(6) . ? O3 C16 1.235(5) . ? O4 C21 1.229(5) . ? O5 C25 1.211(5) . ? O6 C21 1.267(5) . ? O7 C16 1.255(5) . ? O8 C25 1.299(5) . ? O8 H8B 0.72(6) . ? N1 C4 1.314(8) . ? N1 C11 1.473(8) . ? N1 C2 1.479(8) . ? N2 C13 1.339(7) . ? N2 C5 1.472(7) . ? N2 C1 1.491(8) . ? N3 C12 1.317(6) . ? N3 C17 1.332(5) . ? N3 Cu1 2.018(4) 1_656 ? N4 C7 1.332(7) . ? N4 C15 1.341(6) . ? C1 C2 1.420(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C12 1.372(8) . ? C3 C9 1.381(8) . ? C3 H3A 0.9300 . ? C4 C10 1.495(8) . ? C5 C11 1.400(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C8 1.374(10) . ? C6 C10 1.402(10) . ? C6 H6A 0.9300 . ? C7 C8 1.390(8) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C14 1.360(8) . ? C9 H9A 0.9300 . ? C10 C15 1.372(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9300 . ? C13 C14 1.520(7) . ? C14 C17 1.378(6) . ? C15 H15A 0.9300 . ? C16 C18 1.508(5) . ? C17 H17A 0.9300 . ? C18 C24 1.389(6) . ? C18 C20 1.387(5) . ? C19 C22 1.375(6) . ? C19 C24 1.394(5) 2_556 ? C19 C21 1.504(6) . ? C20 C23 1.386(5) . ? C20 H20A 0.9300 . ? C22 C23 1.391(6) 2_556 ? C22 H22A 0.9300 . ? C23 C22 1.391(6) 2_546 ? C23 C25 1.490(6) 4_646 ? C24 C19 1.394(5) 2_546 ? C24 H24A 0.9300 . ? C25 C23 1.490(6) 4_445 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? 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 O7 Cu1 O6 165.47(13) . . ? O7 Cu1 N4 87.46(15) . . ? O6 Cu1 N4 91.66(14) . . ? O7 Cu1 N3 91.03(14) . 1_454 ? O6 Cu1 N3 88.41(14) . 1_454 ? N4 Cu1 N3 174.23(15) . 1_454 ? O7 Cu1 O5 108.59(12) . . ? O6 Cu1 O5 85.95(12) . . ? N4 Cu1 O5 93.56(14) . . ? N3 Cu1 O5 92.20(13) 1_454 . ? C25 O5 Cu1 139.6(3) . . ? C21 O6 Cu1 109.8(3) . . ? C16 O7 Cu1 129.2(3) . . ? C25 O8 H8B 111(5) . . ? C4 N1 C11 126.7(6) . . ? C4 N1 C2 119.6(5) . . ? C11 N1 C2 112.2(5) . . ? C13 N2 C5 121.8(5) . . ? C13 N2 C1 125.5(5) . . ? C5 N2 C1 111.7(5) . . ? C12 N3 C17 117.8(4) . . ? C12 N3 Cu1 122.6(3) . 1_656 ? C17 N3 Cu1 119.6(3) . 1_656 ? C7 N4 C15 118.3(4) . . ? C7 N4 Cu1 122.8(3) . . ? C15 N4 Cu1 118.9(4) . . ? C2 C1 N2 110.9(6) . . ? C2 C1 H1A 109.5 . . ? N2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? N2 C1 H1B 109.5 . . ? H1A C1 H1B 108.0 . . ? C1 C2 N1 109.5(6) . . ? C1 C2 H2A 109.8 . . ? N1 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? N1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C12 C3 C9 118.9(6) . . ? C12 C3 H3A 120.6 . . ? C9 C3 H3A 120.6 . . ? O1 C4 N1 122.3(6) . . ? O1 C4 C10 118.5(6) . . ? N1 C4 C10 119.0(5) . . ? C11 C5 N2 113.9(6) . . ? C11 C5 H5A 108.8 . . ? N2 C5 H5A 108.8 . . ? C11 C5 H5B 108.8 . . ? N2 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C8 C6 C10 120.1(6) . . ? C8 C6 H6A 119.9 . . ? C10 C6 H6A 119.9 . . ? N4 C7 C8 122.8(6) . . ? N4 C7 H7A 118.6 . . ? C8 C7 H7A 118.6 . . ? C6 C8 C7 118.0(7) . . ? C6 C8 H8A 121.0 . . ? C7 C8 H8A 121.0 . . ? C14 C9 C3 118.9(5) . . ? C14 C9 H9A 120.5 . . ? C3 C9 H9A 120.5 . . ? C15 C10 C6 117.3(5) . . ? C15 C10 C4 121.0(6) . . ? C6 C10 C4 121.4(6) . . ? C5 C11 N1 110.8(6) . . ? C5 C11 H11A 109.5 . . ? N1 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N3 C12 C3 122.9(5) . . ? N3 C12 H12A 118.6 . . ? C3 C12 H12A 118.6 . . ? O2 C13 N2 122.4(5) . . ? O2 C13 C14 121.0(5) . . ? N2 C13 C14 116.6(5) . . ? C9 C14 C17 118.3(5) . . ? C9 C14 C13 121.8(5) . . ? C17 C14 C13 119.8(5) . . ? N4 C15 C10 123.5(5) . . ? N4 C15 H15A 118.3 . . ? C10 C15 H15A 118.3 . . ? O3 C16 O7 126.8(4) . . ? O3 C16 C18 116.3(4) . . ? O7 C16 C18 116.9(4) . . ? N3 C17 C14 123.2(5) . . ? N3 C17 H17A 118.4 . . ? C14 C17 H17A 118.4 . . ? C24 C18 C20 119.4(4) . . ? C24 C18 C16 119.2(4) . . ? C20 C18 C16 121.2(4) . . ? C22 C19 C24 119.2(4) . 2_556 ? C22 C19 C21 120.8(4) . . ? C24 C19 C21 119.8(4) 2_556 . ? C23 C20 C18 119.8(4) . . ? C23 C20 H20A 120.1 . . ? C18 C20 H20A 120.1 . . ? O4 C21 O6 124.3(4) . . ? O4 C21 C19 120.3(4) . . ? O6 C21 C19 115.4(4) . . ? C19 C22 C23 120.3(4) . 2_556 ? C19 C22 H22A 119.9 . . ? C23 C22 H22A 119.9 2_556 . ? C20 C23 C22 120.3(4) . 2_546 ? C20 C23 C25 121.8(4) . 4_646 ? C22 C23 C25 117.9(3) 2_546 4_646 ? C18 C24 C19 120.8(4) . 2_546 ? C18 C24 H24A 119.6 . . ? C19 C24 H24A 119.6 2_546 . ? O5 C25 O8 123.7(4) . . ? O5 C25 C23 122.0(4) . 4_445 ? O8 C25 C23 114.2(4) . 4_445 ? H1WA O1W H1WB 93.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.068 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.084 data_compd3 _database_code_depnum_ccdc_archive 'CCDC 768205' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 Cu2 N4 O16' _chemical_formula_weight 875.68 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.415(3) _cell_length_b 19.083(3) _cell_length_c 12.1863(16) _cell_angle_alpha 90.00 _cell_angle_beta 115.048(3) _cell_angle_gamma 90.00 _cell_volume 4722.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4287 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 24.98 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8458 _exptl_absorpt_correction_T_max 0.8851 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11918 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 24.98 _reflns_number_total 4287 _reflns_number_gt 2637 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The bond lengths involving disordered N2A, N2B, C19A, C19B, C20A, C20B were restrained using DFIX instructions. ; _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^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4287 _refine_ls_number_parameters 291 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 0.155256(18) 0.220055(18) 0.30745(4) 0.03441(14) Uani 1 1 d . . . O1 O 0.15535(10) 0.12851(11) 0.3776(2) 0.0419(6) Uani 1 1 d . . . O1W O 0.25165(9) 0.21274(10) 0.38293(19) 0.0423(6) Uani 1 1 d . . . H1A H 0.2754 0.2475 0.3987 0.051 Uiso 1 1 d R . . H1B H 0.2693 0.1845 0.4383 0.051 Uiso 1 1 d R . . O2 O 0.15777(11) 0.18715(11) 0.5364(2) 0.0543(7) Uani 1 1 d . . . O3 O 0.1860(2) 0.05783(18) 0.9060(3) 0.1131(14) Uani 1 1 d . . . H3A H 0.1846 0.0510 0.9713 0.136 Uiso 0.50 1 calc PR . . O4 O 0.16012(10) 0.31286(11) 0.2481(2) 0.0459(6) Uani 1 1 d . . . O5 O 0.18418(13) 0.36921(12) 0.4225(3) 0.0605(8) Uani 1 1 d . . . O6 O 0.1159(3) 0.44147(17) -0.1213(3) 0.165(2) Uani 1 1 d . . . H6A H 0.1193 0.4467 -0.1852 0.198 Uiso 0.50 1 calc PR . . O7 O 0.15435(11) 0.17295(13) 0.1250(2) 0.0490(7) Uani 1 1 d . A . N1 N -0.05602(12) 0.21985(14) -0.2209(2) 0.0392(7) Uani 1 1 d . . . C1 C 0.15777(15) 0.13085(16) 0.4828(4) 0.0371(9) Uani 1 1 d . . . C2 C 0.16160(14) 0.06282(15) 0.5467(3) 0.0325(8) Uani 1 1 d . . . C3 C 0.16922(16) 0.06204(18) 0.6654(3) 0.0447(10) Uani 1 1 d . . . H3 H 0.1715 0.1042 0.7052 0.054 Uiso 1 1 calc R . . C4 C 0.1735(2) 0.0000 0.7258(5) 0.0467(13) Uani 1 2 d S . . C5 C 0.1816(4) 0.0000 0.8527(7) 0.086(2) Uani 1 2 d S . . C6 C 0.15852(19) 0.0000 0.4887(4) 0.0296(11) Uani 1 2 d S . . H6 H 0.1543 0.0000 0.4094 0.036 Uiso 1 2 calc SR . . C7 C 0.17028(15) 0.36859(17) 0.3132(4) 0.0418(9) Uani 1 1 d . . . C8 C 0.16243(16) 0.43652(16) 0.2460(3) 0.0397(9) Uani 1 1 d . . . C9 C 0.1477(2) 0.43690(17) 0.1258(4) 0.0672(13) Uani 1 1 d . . . H9 H 0.1426 0.3946 0.0849 0.081 Uiso 1 1 calc R . . C10 C 0.1400(3) 0.5000 0.0626(5) 0.074(2) Uani 1 2 d S . . C11 C 0.1238(5) 0.5000 -0.0676(7) 0.122(3) Uani 1 2 d S . . C12 C 0.1713(2) 0.5000 0.3070(4) 0.0366(12) Uani 1 2 d S . . H12 H 0.1833 0.5000 0.3900 0.044 Uiso 1 2 calc SR . . C13 C 0.14660(17) 0.2031(2) 0.0321(4) 0.0558(11) Uani 1 1 d . . . C14 C 0.07732(16) 0.2113(2) -0.0655(3) 0.0468(9) Uani 1 1 d . A . C15 C 0.03967(17) 0.1526(2) -0.1053(4) 0.0689(14) Uani 1 1 d . . . H15 H 0.0583 0.1085 -0.0804 0.083 Uiso 1 1 calc R A . C16 C -0.02613(17) 0.15869(19) -0.1828(4) 0.0616(13) Uani 1 1 d . A . H16 H -0.0508 0.1179 -0.2096 0.074 Uiso 1 1 calc R . . C17 C -0.01858(18) 0.27635(19) -0.1831(4) 0.0650(13) Uani 1 1 d . A . H17 H -0.0378 0.3200 -0.2097 0.078 Uiso 1 1 calc R . . C18 C 0.04696(18) 0.2737(2) -0.1066(4) 0.0732(14) Uani 1 1 d . . . H18 H 0.0710 0.3150 -0.0826 0.088 Uiso 1 1 calc R A . N2A N 0.1929(3) 0.2519(4) 0.0245(6) 0.040(2) Uani 0.50 1 d PD A 1 C19A C 0.2594(3) 0.2543(5) 0.1241(6) 0.0416(19) Uani 0.50 1 d PD . 1 H19A H 0.2590 0.2317 0.1951 0.050 Uiso 0.50 1 calc PR . 1 H19B H 0.2726 0.3027 0.1447 0.050 Uiso 0.50 1 calc PR . 1 C20A C 0.1900(4) 0.2833(5) -0.0875(7) 0.043(2) Uani 0.50 1 d PD . 1 H20A H 0.2002 0.3329 -0.0752 0.051 Uiso 0.50 1 calc PR . 1 H20B H 0.1459 0.2783 -0.1517 0.051 Uiso 0.50 1 calc PR . 1 N2B N 0.1976(3) 0.2134(4) 0.0064(6) 0.046(2) Uani 0.50 1 d PD A 2 C19B C 0.2660(4) 0.2026(5) 0.0988(8) 0.051(2) Uani 0.50 1 d PD . 2 H19C H 0.2655 0.1911 0.1760 0.061 Uiso 0.50 1 calc PR . 2 H19D H 0.2857 0.1636 0.0750 0.061 Uiso 0.50 1 calc PR . 2 C20B C 0.1954(5) 0.2352(6) -0.1115(7) 0.057(3) Uani 0.50 1 d PD . 2 H20C H 0.2122 0.1977 -0.1443 0.069 Uiso 0.50 1 calc PR . 2 H20D H 0.1501 0.2441 -0.1680 0.069 Uiso 0.50 1 calc PR . 2 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 0.0326(2) 0.0226(2) 0.0375(3) 0.0029(2) 0.00465(17) -0.00048(18) O1 0.0380(14) 0.0319(13) 0.0455(17) 0.0075(12) 0.0077(13) -0.0001(10) O1W 0.0377(13) 0.0314(12) 0.0426(15) 0.0052(11) 0.0024(11) -0.0041(10) O2 0.0500(15) 0.0265(13) 0.085(2) -0.0083(13) 0.0275(14) -0.0051(11) O3 0.189(4) 0.106(3) 0.062(3) -0.020(2) 0.070(3) 0.005(3) O4 0.0472(14) 0.0227(12) 0.0555(17) 0.0049(12) 0.0098(12) -0.0005(10) O5 0.083(2) 0.0387(15) 0.0459(19) 0.0097(13) 0.0141(15) 0.0073(13) O6 0.349(7) 0.057(2) 0.057(3) -0.0090(19) 0.055(4) -0.006(3) O7 0.0401(15) 0.0667(17) 0.0376(17) -0.0011(14) 0.0140(13) -0.0025(12) N1 0.0323(15) 0.0371(15) 0.0434(18) -0.0009(15) 0.0115(13) -0.0014(14) C1 0.0254(18) 0.0227(18) 0.052(3) -0.0022(17) 0.0059(18) -0.0010(13) C2 0.0289(18) 0.0236(17) 0.039(2) -0.0047(15) 0.0089(17) -0.0041(13) C3 0.049(2) 0.041(2) 0.045(3) -0.0167(18) 0.020(2) -0.0069(16) C4 0.060(4) 0.044(3) 0.035(3) 0.000 0.020(3) 0.000 C5 0.083(5) 0.123(7) 0.057(5) 0.000 0.034(4) 0.000 C6 0.029(2) 0.026(2) 0.029(3) 0.000 0.008(2) 0.000 C7 0.033(2) 0.031(2) 0.049(3) 0.0036(19) 0.0056(19) 0.0025(14) C8 0.043(2) 0.0262(18) 0.041(2) 0.0031(16) 0.0086(18) 0.0007(14) C9 0.107(3) 0.0211(19) 0.054(3) -0.0039(19) 0.014(3) -0.0025(19) C10 0.130(6) 0.035(3) 0.033(4) 0.000 0.013(4) 0.000 C11 0.227(10) 0.042(4) 0.058(5) 0.000 0.023(6) 0.000 C12 0.031(3) 0.031(3) 0.037(3) 0.000 0.004(2) 0.000 C13 0.031(2) 0.097(3) 0.041(3) -0.004(2) 0.0166(19) -0.011(2) C14 0.0304(19) 0.070(3) 0.040(2) 0.001(2) 0.0150(17) -0.0076(19) C15 0.038(2) 0.053(2) 0.084(4) -0.004(2) -0.004(2) 0.0050(19) C16 0.042(2) 0.041(2) 0.075(3) -0.009(2) -0.001(2) -0.0004(18) C17 0.045(2) 0.036(2) 0.093(3) 0.001(2) 0.008(2) -0.0074(19) C18 0.045(2) 0.058(3) 0.095(4) -0.007(3) 0.009(2) -0.021(2) N2A 0.029(4) 0.056(5) 0.032(4) -0.013(4) 0.011(3) -0.011(4) C19A 0.023(4) 0.067(6) 0.027(4) -0.014(4) 0.003(3) -0.010(4) C20A 0.026(5) 0.059(6) 0.035(5) -0.006(4) 0.005(4) -0.012(4) N2B 0.028(4) 0.071(6) 0.027(4) 0.001(4) 0.001(3) -0.009(4) C19B 0.022(5) 0.077(7) 0.038(5) 0.002(5) -0.001(4) 0.002(4) C20B 0.039(6) 0.095(8) 0.024(5) -0.007(5) 0.001(4) -0.017(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.934(2) . ? Cu1 O1 1.945(2) . ? Cu1 O1W 1.962(2) . ? Cu1 N1 2.018(2) 2 ? Cu1 O7 2.390(3) . ? O1 C1 1.260(4) . ? O1W H1A 0.8203 . ? O1W H1B 0.8221 . ? O2 C1 1.257(4) . ? O3 C5 1.263(4) . ? O3 H3A 0.8200 . ? O4 C7 1.288(4) . ? O5 C7 1.234(4) . ? O6 C11 1.269(5) . ? O6 H6A 0.8200 . ? O7 C13 1.216(4) . ? N1 C17 1.324(4) . ? N1 C16 1.328(4) . ? N1 Cu1 2.018(2) 2 ? C1 C2 1.498(4) . ? C2 C6 1.379(4) . ? C2 C3 1.383(5) . ? C3 C4 1.376(4) . ? C3 H3 0.9300 . ? C4 C3 1.376(4) 6 ? C4 C5 1.479(8) . ? C5 O3 1.263(4) 6 ? C6 C2 1.379(4) 6 ? C6 H6 0.9300 . ? C7 C8 1.503(5) . ? C8 C9 1.358(5) . ? C8 C12 1.391(4) . ? C9 C10 1.400(5) . ? C9 H9 0.9300 . ? C10 C9 1.400(5) 6_565 ? C10 C11 1.470(9) . ? C11 O6 1.269(5) 6_565 ? C12 C8 1.391(4) 6_565 ? C12 H12 0.9300 . ? C13 N2B 1.321(8) . ? C13 N2A 1.427(8) . ? C13 C14 1.512(5) . ? C14 C18 1.358(5) . ? C14 C15 1.362(5) . ? C15 C16 1.379(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.367(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N2A C20A 1.467(7) . ? N2A C19A 1.471(7) . ? C19A C20A 1.558(11) 7 ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? C20A C19A 1.558(11) 7 ? C20A H20A 0.9700 . ? C20A H20B 0.9700 . ? N2B C19B 1.482(7) . ? N2B C20B 1.477(8) . ? C19B C20B 1.439(12) 7 ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C20B C19B 1.439(12) 7 ? C20B H20C 0.9700 . ? C20B H20D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O1 176.06(10) . . ? O4 Cu1 O1W 90.88(9) . . ? O1 Cu1 O1W 86.21(9) . . ? O4 Cu1 N1 91.76(10) . 2 ? O1 Cu1 N1 91.36(10) . 2 ? O1W Cu1 N1 174.82(10) . 2 ? O4 Cu1 O7 88.63(10) . . ? O1 Cu1 O7 93.97(10) . . ? O1W Cu1 O7 89.05(9) . . ? N1 Cu1 O7 86.56(10) 2 . ? C1 O1 Cu1 114.0(2) . . ? Cu1 O1W H1A 121.9 . . ? Cu1 O1W H1B 118.8 . . ? H1A O1W H1B 107.5 . . ? C5 O3 H3A 109.5 . . ? C7 O4 Cu1 123.3(2) . . ? C11 O6 H6A 109.5 . . ? C13 O7 Cu1 129.1(3) . . ? C17 N1 C16 116.3(3) . . ? C17 N1 Cu1 125.2(2) . 2 ? C16 N1 Cu1 117.8(2) . 2 ? O2 C1 O1 123.3(3) . . ? O2 C1 C2 118.9(4) . . ? O1 C1 C2 117.8(3) . . ? C6 C2 C3 119.0(3) . . ? C6 C2 C1 120.5(3) . . ? C3 C2 C1 120.5(3) . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C3 118.8(5) . 6 ? C3 C4 C5 120.6(2) . . ? C3 C4 C5 120.6(2) 6 . ? O3 C5 O3 121.8(7) 6 . ? O3 C5 C4 119.1(4) 6 . ? O3 C5 C4 119.1(4) . . ? C2 C6 C2 120.8(5) . 6 ? C2 C6 H6 119.6 . . ? C2 C6 H6 119.6 6 . ? O5 C7 O4 124.8(3) . . ? O5 C7 C8 119.8(3) . . ? O4 C7 C8 115.3(4) . . ? C9 C8 C12 119.1(3) . . ? C9 C8 C7 120.7(3) . . ? C12 C8 C7 120.2(4) . . ? C8 C9 C10 121.0(4) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C9 118.6(6) 6_565 . ? C9 C10 C11 120.7(3) 6_565 . ? C9 C10 C11 120.7(3) . . ? O6 C11 O6 123.4(7) . 6_565 ? O6 C11 C10 118.3(4) . . ? O6 C11 C10 118.3(4) 6_565 . ? C8 C12 C8 121.1(5) 6_565 . ? C8 C12 H12 119.4 6_565 . ? C8 C12 H12 119.4 . . ? O7 C13 N2B 119.6(4) . . ? O7 C13 N2A 123.2(4) . . ? O7 C13 C14 118.4(3) . . ? N2B C13 C14 120.1(4) . . ? N2A C13 C14 114.5(4) . . ? C18 C14 C15 116.8(3) . . ? C18 C14 C13 124.6(3) . . ? C15 C14 C13 118.1(4) . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? N1 C16 C15 123.3(3) . . ? N1 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? N1 C17 C18 123.2(3) . . ? N1 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C14 C18 C17 120.7(3) . . ? C14 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C13 N2A C20A 125.4(6) . . ? C13 N2A C19A 118.5(6) . . ? C20A N2A C19A 112.7(7) . . ? N2A C19A C20A 110.9(7) . 7 ? N2A C19A H19A 109.5 . . ? C20A C19A H19A 109.5 7 . ? N2A C19A H19B 109.5 . . ? C20A C19A H19B 109.5 7 . ? H19A C19A H19B 108.1 . . ? N2A C20A C19A 109.1(7) . 7 ? N2A C20A H20A 109.9 . . ? C19A C20A H20A 109.9 7 . ? N2A C20A H20B 109.9 . . ? C19A C20A H20B 109.9 7 . ? H20A C20A H20B 108.3 . . ? C13 N2B C19B 121.3(6) . . ? C13 N2B C20B 126.6(6) . . ? C19B N2B C20B 112.1(8) . . ? C20B C19B N2B 110.4(8) 7 . ? C20B C19B H19C 109.6 7 . ? N2B C19B H19C 109.6 . . ? C20B C19B H19D 109.6 7 . ? N2B C19B H19D 109.6 . . ? H19C C19B H19D 108.1 . . ? C19B C20B N2B 110.9(8) 7 . ? C19B C20B H20C 109.5 7 . ? N2B C20B H20C 109.5 . . ? C19B C20B H20D 109.5 7 . ? N2B C20B H20D 109.5 . . ? H20C C20B H20D 108.0 . . ? 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 O1W H1A O2 0.82 1.85 2.655(3) 167 7_556 O1W H1B O5 0.82 1.88 2.692(3) 172 7_556 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.365 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.059 data_compd2 _database_code_depnum_ccdc_archive 'CCDC 796977' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H21 Cu N4 O8.50' _chemical_formula_weight 577.00 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 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 9.8482(11) _cell_length_b 20.186(2) _cell_length_c 13.7326(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.857(2) _cell_angle_gamma 90.00 _cell_volume 2726.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2352 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 21.99 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8209 _exptl_absorpt_correction_T_max 0.9117 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13637 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.11 _reflns_number_total 4841 _reflns_number_gt 3327 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1148P)^2^+2.7962P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4841 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1889 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.68948(6) 0.12285(2) 0.84084(4) 0.0311(2) Uani 1 1 d . . . O1 O 0.6185(4) 0.03318(14) 0.8521(2) 0.0374(8) Uani 1 1 d . . . O2 O 0.7579(4) 0.01364(17) 0.7343(3) 0.0615(12) Uani 1 1 d . . . O3 O 0.8184(4) -0.21494(18) 0.6260(3) 0.0587(12) Uani 1 1 d . . . O4 O 0.7090(4) -0.29861(15) 0.6921(2) 0.0387(8) Uani 1 1 d . . . O5 O 0.4742(4) -0.15276(16) 1.0549(2) 0.0426(9) Uani 1 1 d . . . O6 O 0.4393(5) -0.24880(18) 0.9799(3) 0.0695(14) Uani 1 1 d . . . H6 H 0.3920 -0.2558 1.0263 0.083 Uiso 1 1 calc R . . O7 O 0.8029(6) -0.0299(2) 1.2121(3) 0.0802(15) Uani 1 1 d . . . O8 O 0.6019(9) 0.2473(3) 1.4336(4) 0.149(3) Uani 1 1 d . . . N1 N 0.8240(4) 0.10209(19) 0.9521(3) 0.0358(9) Uani 1 1 d . . . N2 N 0.7627(8) 0.0710(3) 1.2698(4) 0.0812(19) Uani 1 1 d . . . N3 N 0.7166(7) 0.1531(3) 1.4274(4) 0.0799(19) Uani 1 1 d . . . N4 N 0.5694(5) 0.1399(2) 1.7218(3) 0.0397(10) Uani 1 1 d . . . C1 C 0.6781(5) -0.0051(2) 0.7949(4) 0.0347(11) Uani 1 1 d . . . C2 C 0.6493(5) -0.0776(2) 0.8075(3) 0.0291(10) Uani 1 1 d . . . C3 C 0.6981(5) -0.1230(2) 0.7410(3) 0.0304(10) Uani 1 1 d . . . H3 H 0.7449 -0.1079 0.6882 0.037 Uiso 1 1 calc R . . C4 C 0.6772(5) -0.1908(2) 0.7531(3) 0.0302(10) Uani 1 1 d . . . C5 C 0.6065(5) -0.2128(2) 0.8316(3) 0.0315(11) Uani 1 1 d . . . H5 H 0.5899 -0.2578 0.8395 0.038 Uiso 1 1 calc R . . C6 C 0.5608(5) -0.1677(2) 0.8983(3) 0.0292(10) Uani 1 1 d . . . C7 C 0.5846(5) -0.1002(2) 0.8867(3) 0.0304(10) Uani 1 1 d . . . H7 H 0.5562 -0.0703 0.9331 0.037 Uiso 1 1 calc R . . C8 C 0.7411(5) -0.2388(2) 0.6841(3) 0.0347(11) Uani 1 1 d . . . C9 C 0.4888(5) -0.1895(2) 0.9862(3) 0.0350(11) Uani 1 1 d . . . C10 C 0.9555(6) 0.1157(3) 0.9487(4) 0.0558(16) Uani 1 1 d . . . H10 H 0.9865 0.1359 0.8932 0.067 Uiso 1 1 calc R . . C11 C 1.0477(7) 0.1012(4) 1.0240(5) 0.079(2) Uani 1 1 d . . . H11 H 1.1397 0.1103 1.0187 0.094 Uiso 1 1 calc R . . C12 C 1.0011(7) 0.0727(4) 1.1080(5) 0.071(2) Uani 1 1 d . . . H12 H 1.0614 0.0623 1.1600 0.085 Uiso 1 1 calc R . . C13 C 0.8659(6) 0.0603(3) 1.1132(4) 0.0457(13) Uani 1 1 d . . . C14 C 0.7814(5) 0.0741(2) 1.0331(3) 0.0393(12) Uani 1 1 d . . . H14 H 0.6898 0.0634 1.0355 0.047 Uiso 1 1 calc R . . C15 C 0.8083(6) 0.0293(3) 1.2027(4) 0.0504(14) Uani 1 1 d . . . C16 C 0.7494(12) 0.1441(4) 1.2581(5) 0.098(3) Uani 1 1 d . . . H16A H 0.8031 0.1588 1.2049 0.118 Uiso 1 1 calc R . . H16B H 0.6551 0.1554 1.2422 0.118 Uiso 1 1 calc R . . C17 C 0.7942(10) 0.1773(4) 1.3455(5) 0.096(3) Uani 1 1 d . . . H17A H 0.7811 0.2246 1.3378 0.115 Uiso 1 1 calc R . . H17B H 0.8904 0.1690 1.3588 0.115 Uiso 1 1 calc R . . C18 C 0.7296(9) 0.0810(4) 1.4422(5) 0.086(2) Uani 1 1 d . . . H18A H 0.8224 0.0703 1.4635 0.104 Uiso 1 1 calc R . . H18B H 0.6705 0.0671 1.4928 0.104 Uiso 1 1 calc R . . C19 C 0.6947(9) 0.0467(4) 1.3556(5) 0.087(3) Uani 1 1 d . . . H19A H 0.5971 0.0498 1.3428 0.104 Uiso 1 1 calc R . . H19B H 0.7169 0.0002 1.3650 0.104 Uiso 1 1 calc R . . C20 C 0.6255(9) 0.1924(3) 1.4644(4) 0.074(2) Uani 1 1 d . . . C21 C 0.5548(7) 0.1696(3) 1.5530(4) 0.0581(16) Uani 1 1 d . . . C22 C 0.4112(9) 0.1698(5) 1.5552(6) 0.095(3) Uani 1 1 d . . . H22 H 0.3576 0.1800 1.4995 0.114 Uiso 1 1 calc R . . C23 C 0.3524(8) 0.1548(5) 1.6409(5) 0.093(3) Uani 1 1 d . . . H23 H 0.2583 0.1548 1.6441 0.112 Uiso 1 1 calc R . . C24 C 0.4344(7) 0.1396(3) 1.7222(4) 0.0608(17) Uani 1 1 d . . . H24 H 0.3935 0.1286 1.7797 0.073 Uiso 1 1 calc R . . C25 C 0.6280(6) 0.1537(2) 1.6373(4) 0.0438(13) Uani 1 1 d . . . H25 H 0.7223 0.1525 1.6363 0.053 Uiso 1 1 calc R . . O1W O 0.9714(10) 0.0834(7) 0.6518(9) 0.123(5) Uani 0.50 1 d P . . H1A H 0.9057 0.0618 0.6686 0.147 Uiso 0.50 1 d PR . . H1B H 1.0385 0.0730 0.6866 0.147 Uiso 0.50 1 d PR . . 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 0.0506(4) 0.0187(3) 0.0248(3) 0.0025(2) 0.0111(2) -0.0012(2) O1 0.058(2) 0.0186(16) 0.0369(18) -0.0018(13) 0.0130(16) 0.0022(14) O2 0.078(3) 0.031(2) 0.080(3) 0.0071(19) 0.053(2) -0.0030(19) O3 0.091(3) 0.036(2) 0.054(2) -0.0060(17) 0.051(2) 0.0028(19) O4 0.054(2) 0.0248(17) 0.0379(19) -0.0097(14) 0.0123(16) 0.0037(15) O5 0.062(2) 0.0341(19) 0.0337(19) -0.0060(15) 0.0242(17) -0.0030(16) O6 0.121(4) 0.038(2) 0.054(3) -0.0143(18) 0.061(3) -0.032(2) O7 0.131(4) 0.052(3) 0.060(3) 0.008(2) 0.032(3) -0.003(3) O8 0.276(9) 0.091(5) 0.088(4) 0.047(4) 0.084(5) 0.093(5) N1 0.045(3) 0.030(2) 0.033(2) 0.0018(17) 0.0110(19) -0.0027(18) N2 0.155(6) 0.049(3) 0.042(3) 0.006(2) 0.034(3) -0.006(3) N3 0.129(5) 0.051(3) 0.064(4) 0.011(3) 0.041(4) 0.009(3) N4 0.056(3) 0.031(2) 0.032(2) 0.0017(17) 0.007(2) 0.0036(19) C1 0.043(3) 0.022(2) 0.040(3) 0.000(2) 0.009(2) -0.001(2) C2 0.039(3) 0.020(2) 0.029(2) -0.0007(18) 0.010(2) 0.0002(19) C3 0.037(3) 0.026(2) 0.029(2) 0.0012(19) 0.014(2) -0.001(2) C4 0.039(3) 0.025(2) 0.028(2) -0.0058(18) 0.013(2) 0.0022(19) C5 0.045(3) 0.021(2) 0.030(2) -0.0004(18) 0.012(2) -0.004(2) C6 0.038(3) 0.023(2) 0.028(2) -0.0019(18) 0.013(2) -0.0004(19) C7 0.038(3) 0.024(2) 0.031(2) -0.0076(19) 0.009(2) 0.0035(19) C8 0.052(3) 0.027(2) 0.026(2) -0.0035(19) 0.011(2) 0.003(2) C9 0.048(3) 0.022(2) 0.037(3) -0.002(2) 0.018(2) -0.001(2) C10 0.059(4) 0.058(4) 0.051(4) 0.018(3) 0.012(3) -0.003(3) C11 0.046(4) 0.111(6) 0.078(5) 0.037(4) -0.004(3) -0.013(4) C12 0.059(4) 0.094(5) 0.058(4) 0.023(4) -0.013(3) -0.006(4) C13 0.055(4) 0.042(3) 0.040(3) 0.007(2) 0.005(3) 0.005(3) C14 0.044(3) 0.039(3) 0.035(3) 0.006(2) 0.010(2) 0.003(2) C15 0.069(4) 0.051(4) 0.030(3) 0.008(3) 0.002(3) 0.006(3) C16 0.179(9) 0.068(5) 0.049(4) 0.006(4) 0.018(5) -0.007(5) C17 0.153(8) 0.069(5) 0.068(5) 0.000(4) 0.038(5) -0.019(5) C18 0.134(7) 0.071(5) 0.057(4) 0.008(4) 0.032(4) 0.021(5) C19 0.144(8) 0.067(5) 0.052(4) 0.013(3) 0.035(4) -0.007(4) C20 0.127(6) 0.068(4) 0.029(3) 0.009(3) 0.010(4) 0.029(4) C21 0.081(5) 0.060(4) 0.033(3) 0.001(3) 0.003(3) 0.016(3) C22 0.099(7) 0.128(7) 0.056(5) 0.019(5) -0.014(4) 0.025(5) C23 0.062(5) 0.159(9) 0.059(5) 0.012(5) -0.008(4) 0.016(5) C24 0.061(4) 0.079(5) 0.043(3) -0.001(3) 0.007(3) -0.001(3) C25 0.067(4) 0.034(3) 0.030(3) 0.000(2) 0.008(3) 0.011(2) O1W 0.051(6) 0.191(13) 0.127(10) 0.102(10) 0.007(6) -0.025(7) _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 O4 1.940(3) 2_656 ? Cu1 O1 1.949(3) . ? Cu1 N4 2.000(4) 1_554 ? Cu1 N1 2.016(4) . ? Cu1 O5 2.290(3) 3_657 ? O1 C1 1.267(5) . ? O2 C1 1.232(6) . ? O3 C8 1.228(6) . ? O4 C8 1.254(5) . ? O4 Cu1 1.940(3) 2_646 ? O5 C9 1.214(5) . ? O5 Cu1 2.290(3) 3_657 ? O6 C9 1.295(6) . ? O6 H6 0.8200 . ? O7 C15 1.204(7) . ? O8 C20 1.206(8) . ? N1 C10 1.327(7) . ? N1 C14 1.334(6) . ? N2 C15 1.340(8) . ? N2 C16 1.491(9) . ? N2 C19 1.469(8) . ? N3 C20 1.318(8) . ? N3 C18 1.475(9) . ? N3 C17 1.475(8) . ? N4 C24 1.330(7) . ? N4 C25 1.350(6) . ? N4 Cu1 2.000(4) 1_556 ? C1 C2 1.502(6) . ? C2 C7 1.365(6) . ? C2 C3 1.396(6) . ? C3 C4 1.395(6) . ? C3 H3 0.9300 . ? C4 C5 1.386(6) . ? C4 C8 1.514(6) . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 C7 1.394(6) . ? C6 C9 1.496(6) . ? C7 H7 0.9300 . ? C10 C11 1.373(9) . ? C10 H10 0.9300 . ? C11 C12 1.388(9) . ? C11 H11 0.9300 . ? C12 C13 1.360(8) . ? C12 H12 0.9300 . ? C13 C14 1.375(7) . ? C13 C15 1.515(7) . ? C14 H14 0.9300 . ? C16 C17 1.424(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.404(10) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.503(9) . ? C21 C25 1.371(8) . ? C21 C22 1.416(11) . ? C22 C23 1.371(10) . ? C22 H22 0.9300 . ? C23 C24 1.379(9) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? O1W H1A 0.8229 . ? O1W H1B 0.8228 . ? 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 Cu1 O1 165.58(14) 2_656 . ? O4 Cu1 N4 87.67(16) 2_656 1_554 ? O1 Cu1 N4 91.41(16) . 1_554 ? O4 Cu1 N1 91.13(15) 2_656 . ? O1 Cu1 N1 88.38(15) . . ? N4 Cu1 N1 174.38(16) 1_554 . ? O4 Cu1 O5 108.52(13) 2_656 3_657 ? O1 Cu1 O5 85.91(13) . 3_657 ? N4 Cu1 O5 93.44(16) 1_554 3_657 ? N1 Cu1 O5 92.15(14) . 3_657 ? C1 O1 Cu1 109.7(3) . . ? C8 O4 Cu1 129.1(3) . 2_646 ? C9 O5 Cu1 139.6(3) . 3_657 ? C9 O6 H6 109.5 . . ? C10 N1 C14 117.7(5) . . ? C10 N1 Cu1 122.4(4) . . ? C14 N1 Cu1 119.8(3) . . ? C15 N2 C16 125.3(5) . . ? C15 N2 C19 121.6(6) . . ? C16 N2 C19 112.0(6) . . ? C20 N3 C18 126.6(6) . . ? C20 N3 C17 119.0(6) . . ? C18 N3 C17 112.8(6) . . ? C24 N4 C25 118.4(5) . . ? C24 N4 Cu1 123.1(4) . 1_556 ? C25 N4 Cu1 118.5(4) . 1_556 ? O2 C1 O1 124.2(4) . . ? O2 C1 C2 120.5(4) . . ? O1 C1 C2 115.2(4) . . ? C7 C2 C3 119.4(4) . . ? C7 C2 C1 121.0(4) . . ? C3 C2 C1 119.4(4) . . ? C4 C3 C2 120.6(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.3(4) . . ? C5 C4 C8 121.5(4) . . ? C3 C4 C8 119.0(4) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.4(4) . . ? C5 C6 C9 121.6(4) . . ? C7 C6 C9 118.0(4) . . ? C2 C7 C6 120.3(4) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O3 C8 O4 127.0(4) . . ? O3 C8 C4 116.5(4) . . ? O4 C8 C4 116.5(4) . . ? O5 C9 O6 123.9(4) . . ? O5 C9 C6 121.8(4) . . ? O6 C9 C6 114.2(4) . . ? N1 C10 C11 122.7(5) . . ? N1 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C10 C11 C12 118.7(6) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 119.0(6) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 118.5(5) . . ? C12 C13 C15 121.7(5) . . ? C14 C13 C15 119.8(5) . . ? N1 C14 C13 123.3(5) . . ? N1 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? O7 C15 N2 122.0(5) . . ? O7 C15 C13 121.2(5) . . ? N2 C15 C13 116.8(5) . . ? C17 C16 N2 110.7(7) . . ? C17 C16 H16A 109.5 . . ? N2 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C16 C17 N3 109.6(7) . . ? C16 C17 H17A 109.7 . . ? N3 C17 H17A 109.7 . . ? C16 C17 H17B 109.7 . . ? N3 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C19 C18 N3 110.7(6) . . ? C19 C18 H18A 109.5 . . ? N3 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C18 C19 N2 114.4(7) . . ? C18 C19 H19A 108.7 . . ? N2 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? N2 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? O8 C20 N3 122.7(7) . . ? O8 C20 C21 118.5(6) . . ? N3 C20 C21 118.6(6) . . ? C25 C21 C22 117.8(6) . . ? C25 C21 C20 120.6(6) . . ? C22 C21 C20 121.3(6) . . ? C23 C22 C21 118.8(7) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C22 C23 C24 119.3(7) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? N4 C24 C23 122.7(6) . . ? N4 C24 H24 118.7 . . ? C23 C24 H24 118.7 . . ? N4 C25 C21 123.0(6) . . ? N4 C25 H25 118.5 . . ? C21 C25 H25 118.5 . . ? H1A O1W H1B 108.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O3 0.82 1.69 2.493(5) 167 4_556 O1W H1A O2 0.82 2.00 2.815(10) 170 . O1W H1B O7 0.82 2.22 3.031(12) 170 3_757 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.072 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.088