# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Akhil R. Chakravarty' _publ_contact_author_email ARC@IPC.IISC.ERNET.IN _publ_section_title ; DNA cleavage in red light promoted by copper(II) complexes of ?-amino acids and photoactive phenanthroline bases ; loop_ _publ_author_name 'Akhil R. Chakravarty' 'Tuhin Bhowmick' 'Munirathinam Nethaji' 'Ashis K Patra' 'Suryanarayanarao Ramakumar' # Attachment 'dtarc1revised-5july08.txt' data_arc1 _database_code_depnum_ccdc_archive 'CCDC 678816' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration rm _chemical_formula_moiety 'C30 H27 Cu N7 O7' _chemical_formula_sum 'C30 H27 Cu N7 O7' _chemical_formula_weight 661.13 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.051(3) _cell_length_b 10.204(3) _cell_length_c 18.490(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.632(5) _cell_angle_gamma 90.00 _cell_volume 1517.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangle _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 682 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8598 _exptl_absorpt_correction_T_max 0.8922 _exptl_absorpt_process_details SADABS(Sheldrick,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 'Bruker Smart CCD Area Detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11720 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 26.04 _reflns_number_total 5823 _reflns_number_gt 5406 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0985P)^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 0.045(15) _refine_ls_number_reflns 5823 _refine_ls_number_parameters 405 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1403 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.17332(5) 0.46919(5) 0.89689(2) 0.03205(14) Uani 1 1 d . . . C1 C 0.2447(5) 0.2265(4) 0.8111(2) 0.0409(9) Uani 1 1 d . . . H1 H 0.1874 0.1790 0.8449 0.049 Uiso 1 1 calc R . . C2 C 0.3039(6) 0.1617(4) 0.7513(2) 0.0467(10) Uani 1 1 d . . . H2 H 0.2847 0.0724 0.7452 0.056 Uiso 1 1 calc R . . C3 C 0.3908(5) 0.2299(4) 0.7014(2) 0.0409(9) Uani 1 1 d . . . H3 H 0.4333 0.1869 0.6620 0.049 Uiso 1 1 calc R . . C4 C 0.4146(5) 0.3646(4) 0.7106(2) 0.0319(8) Uani 1 1 d . . . C5 C 0.4992(5) 0.4461(4) 0.65915(19) 0.0326(9) Uani 1 1 d . . . C6 C 0.6318(5) 0.4673(7) 0.55377(18) 0.0402(8) Uani 1 1 d . . . C7 C 0.6925(7) 0.4126(6) 0.4895(3) 0.0555(12) Uani 1 1 d . . . H7 H 0.6756 0.3244 0.4790 0.067 Uiso 1 1 calc R . . C8 C 0.7757(7) 0.4901(7) 0.4434(2) 0.0650(16) Uani 1 1 d . . . H8 H 0.8167 0.4536 0.4017 0.078 Uiso 1 1 calc R . . C9 C 0.8006(7) 0.6234(6) 0.4574(3) 0.0588(13) Uani 1 1 d . . . H9 H 0.8593 0.6739 0.4253 0.071 Uiso 1 1 calc R . . C10 C 0.7390(6) 0.6814(5) 0.5184(2) 0.0515(11) Uani 1 1 d . . . H10 H 0.7541 0.7706 0.5269 0.062 Uiso 1 1 calc R . . C11 C 0.6546(5) 0.6051(4) 0.5668(2) 0.0394(9) Uani 1 1 d . . . C12 C 0.5217(4) 0.5830(4) 0.67375(19) 0.0319(8) Uani 1 1 d . . . C13 C 0.4594(5) 0.6403(4) 0.73917(19) 0.0311(8) Uani 1 1 d . . . C14 C 0.4834(6) 0.7717(4) 0.7596(2) 0.0415(9) Uani 1 1 d . . . H14 H 0.5431 0.8277 0.7308 0.050 Uiso 1 1 calc R . . C15 C 0.4186(6) 0.8171(4) 0.8221(2) 0.0427(9) Uani 1 1 d . . . H15 H 0.4360 0.9033 0.8369 0.051 Uiso 1 1 calc R . . C16 C 0.3267(5) 0.7322(4) 0.8628(2) 0.0386(9) Uani 1 1 d . . . H16 H 0.2788 0.7646 0.9040 0.046 Uiso 1 1 calc R . . C17 C 0.3703(5) 0.5610(4) 0.7856(2) 0.0309(8) Uani 1 1 d . . . C18 C 0.3498(5) 0.4231(4) 0.7715(2) 0.0286(8) Uani 1 1 d . . . C19 C -0.0957(5) 0.3558(4) 0.95481(19) 0.0372(9) Uani 1 1 d . . . C20 C -0.1482(5) 0.4972(4) 0.9487(2) 0.0379(10) Uani 1 1 d . . . H20 H -0.2064 0.5223 0.9920 0.046 Uiso 1 1 calc R . . C21 C -0.2649(5) 0.5143(4) 0.8818(2) 0.0386(9) Uani 1 1 d . . . H21A H -0.3686 0.4695 0.8901 0.046 Uiso 1 1 calc R . . H21B H -0.2898 0.6068 0.8758 0.046 Uiso 1 1 calc R . . C22 C -0.1970(4) 0.4633(5) 0.81284(18) 0.0360(7) Uani 1 1 d . . . C23 C -0.1061(5) 0.5355(4) 0.7595(2) 0.0362(9) Uani 1 1 d . . . C24 C -0.0575(5) 0.6655(4) 0.7521(2) 0.0421(9) Uani 1 1 d . . . H24 H -0.0832 0.7272 0.7868 0.051 Uiso 1 1 calc R . . C25 C 0.0289(6) 0.7017(5) 0.6929(3) 0.0524(11) Uani 1 1 d . . . H25 H 0.0605 0.7888 0.6879 0.063 Uiso 1 1 calc R . . C26 C 0.0705(6) 0.6112(6) 0.6401(3) 0.0558(13) Uani 1 1 d . . . H26 H 0.1298 0.6384 0.6008 0.067 Uiso 1 1 calc R . . C27 C 0.0231(5) 0.4793(8) 0.6461(2) 0.0568(13) Uani 1 1 d . . . H27 H 0.0493 0.4177 0.6113 0.068 Uiso 1 1 calc R . . C28 C -0.0634(5) 0.4453(4) 0.7055(2) 0.0405(10) Uani 1 1 d . . . C29 C -0.2026(6) 0.3373(4) 0.7891(2) 0.0470(11) Uani 1 1 d . . . H29 H -0.2536 0.2690 0.8129 0.056 Uiso 1 1 calc R . . C30 C 0.7741(8) 1.0071(6) 0.6442(3) 0.0703(15) Uani 1 1 d . . . N1 N 0.2677(4) 0.3549(3) 0.82147(17) 0.0310(7) Uani 1 1 d . . . N2 N 0.3035(4) 0.6070(3) 0.84606(17) 0.0309(7) Uani 1 1 d . . . N3 N 0.5959(4) 0.6618(3) 0.62775(17) 0.0371(7) Uani 1 1 d . . . N4 N 0.5526(5) 0.3900(4) 0.59993(18) 0.0398(8) Uani 1 1 d . . . N5 N 0.0047(4) 0.5821(4) 0.94267(18) 0.0350(8) Uani 1 1 d . . . H5A H 0.0426 0.6091 0.9867 0.042 Uiso 1 1 calc R . . H5B H -0.0186 0.6529 0.9151 0.042 Uiso 1 1 calc R . . N6 N -0.1238(5) 0.3241(4) 0.7260(2) 0.0481(9) Uani 1 1 d . . . H6 H -0.1131 0.2521 0.7025 0.058 Uiso 1 1 calc R . . N7 N 0.8855(6) 0.9613(5) 0.85009(19) 0.0580(9) Uani 1 1 d . . . O1 O 0.0516(4) 0.3252(3) 0.93645(16) 0.0386(7) Uani 1 1 d . . . O2 O -0.1989(4) 0.2732(3) 0.97338(18) 0.0534(8) Uani 1 1 d . . . O3 O 0.3582(4) 0.4432(3) 0.99560(16) 0.0502(8) Uani 1 1 d . . . O4 O 0.7514(6) 1.0100(5) 0.8296(3) 0.0918(15) Uani 1 1 d . . . O5 O 0.8870(8) 0.8896(6) 0.9053(2) 0.1016(18) Uani 1 1 d . . . O6 O 1.0062(5) 0.9746(6) 0.8137(2) 0.0797(10) Uani 1 1 d . . . O7 O 0.9242(4) 1.0626(4) 0.67550(19) 0.0308(7) Uiso 0.70 1 d P . . O7' O 0.7423(10) 1.0615(8) 0.5710(4) 0.0304(17) Uiso 0.30 1 d P . . 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 0.0332(2) 0.0334(2) 0.0302(2) 0.0010(2) 0.00844(15) -0.0012(2) C1 0.043(2) 0.037(2) 0.044(2) 0.0004(17) 0.0105(18) -0.0054(17) C2 0.059(3) 0.035(2) 0.047(2) -0.0063(18) 0.011(2) -0.0056(19) C3 0.042(2) 0.039(2) 0.042(2) -0.0079(17) 0.0020(17) 0.0046(18) C4 0.0302(19) 0.0348(19) 0.0308(18) -0.0021(15) 0.0015(15) -0.0017(15) C5 0.0312(17) 0.040(3) 0.0265(16) -0.0005(15) 0.0038(13) 0.0020(15) C6 0.0399(19) 0.052(2) 0.0298(16) 0.004(2) 0.0082(14) 0.014(3) C7 0.071(3) 0.056(3) 0.040(2) -0.003(2) 0.014(2) 0.010(2) C8 0.078(3) 0.084(5) 0.035(2) 0.006(3) 0.025(2) 0.013(3) C9 0.063(3) 0.072(4) 0.042(3) 0.015(2) 0.018(2) 0.006(3) C10 0.055(3) 0.059(3) 0.042(2) 0.007(2) 0.015(2) -0.003(2) C11 0.040(2) 0.050(2) 0.0289(19) 0.0050(16) 0.0027(16) 0.0040(18) C12 0.0291(18) 0.038(2) 0.0290(18) -0.0002(15) 0.0014(14) 0.0032(15) C13 0.0328(19) 0.0324(19) 0.0284(17) 0.0042(15) 0.0038(14) 0.0001(15) C14 0.047(2) 0.039(2) 0.039(2) 0.0011(17) 0.0114(17) -0.0097(18) C15 0.052(3) 0.036(2) 0.040(2) -0.0015(17) 0.0082(18) -0.0057(18) C16 0.043(2) 0.040(2) 0.033(2) -0.0077(16) 0.0087(17) -0.0014(17) C17 0.0272(19) 0.0317(19) 0.0335(19) 0.0018(15) -0.0002(15) -0.0009(15) C18 0.0259(18) 0.0318(18) 0.0283(18) -0.0014(14) 0.0017(14) -0.0002(14) C19 0.039(2) 0.049(2) 0.0237(17) 0.0060(16) 0.0002(16) -0.0099(18) C20 0.0316(19) 0.052(3) 0.0305(18) 0.0013(16) 0.0091(14) -0.0016(17) C21 0.0283(19) 0.048(2) 0.040(2) 0.0092(16) 0.0045(16) 0.0054(15) C22 0.0364(17) 0.0377(18) 0.0332(16) 0.005(2) -0.0063(13) -0.001(2) C23 0.035(2) 0.036(2) 0.037(2) 0.0012(16) -0.0068(16) 0.0049(16) C24 0.039(2) 0.039(2) 0.047(2) -0.0011(18) -0.0041(18) 0.0007(17) C25 0.057(3) 0.049(3) 0.050(3) 0.008(2) -0.001(2) -0.007(2) C26 0.043(3) 0.074(4) 0.050(3) 0.018(2) 0.002(2) -0.001(2) C27 0.051(2) 0.081(4) 0.038(2) -0.009(3) -0.0059(17) 0.025(3) C28 0.041(2) 0.044(3) 0.0359(19) -0.0006(17) -0.0077(16) 0.0072(17) C29 0.056(3) 0.042(2) 0.041(2) 0.0057(19) -0.014(2) -0.008(2) C30 0.070(4) 0.068(4) 0.074(4) 0.003(3) 0.004(3) -0.010(3) N1 0.0329(17) 0.0303(16) 0.0298(16) 0.0004(13) 0.0013(13) -0.0028(13) N2 0.0325(17) 0.0353(17) 0.0253(16) -0.0020(13) 0.0068(13) -0.0013(13) N3 0.0352(17) 0.0436(19) 0.0328(16) 0.0040(14) 0.0053(13) 0.0010(14) N4 0.043(2) 0.0447(19) 0.0321(17) -0.0026(14) 0.0065(14) 0.0045(15) N5 0.0348(19) 0.0428(19) 0.0279(16) -0.0039(14) 0.0054(14) -0.0006(15) N6 0.058(2) 0.0369(19) 0.048(2) -0.0099(16) -0.0109(18) 0.0018(17) N7 0.079(3) 0.053(2) 0.0428(18) -0.009(2) 0.0069(19) -0.005(3) O1 0.0349(16) 0.0417(16) 0.0399(15) 0.0076(13) 0.0091(12) -0.0023(13) O2 0.0466(17) 0.061(2) 0.0534(17) 0.0224(15) 0.0084(14) -0.0097(15) O3 0.0472(16) 0.061(2) 0.0423(14) -0.0038(14) -0.0033(12) 0.0048(14) O4 0.084(3) 0.096(4) 0.094(3) 0.023(3) -0.008(3) -0.017(3) O5 0.140(5) 0.111(4) 0.056(2) 0.029(2) 0.033(3) 0.045(3) O6 0.086(3) 0.079(2) 0.077(2) -0.001(3) 0.030(2) -0.017(3) _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 1.929(3) . ? Cu1 N1 1.995(3) . ? Cu1 N5 1.998(4) . ? Cu1 N2 2.012(3) . ? Cu1 O3 2.317(3) . ? C1 N1 1.335(5) . ? C1 C2 1.391(6) . ? C1 H1 0.9300 . ? C2 C3 1.373(6) . ? C2 H2 0.9300 . ? C3 C4 1.397(6) . ? C3 H3 0.9300 . ? C4 C18 1.397(5) . ? C4 C5 1.456(5) . ? C5 N4 1.325(5) . ? C5 C12 1.433(6) . ? C6 N4 1.344(6) . ? C6 C7 1.420(6) . ? C6 C11 1.437(8) . ? C7 C8 1.361(7) . ? C7 H7 0.9300 . ? C8 C9 1.398(9) . ? C8 H8 0.9300 . ? C9 C10 1.386(7) . ? C9 H9 0.9300 . ? C10 C11 1.387(6) . ? C10 H10 0.9300 . ? C11 N3 1.370(5) . ? C12 N3 1.331(5) . ? C12 C13 1.454(5) . ? C13 C17 1.401(5) . ? C13 C14 1.404(6) . ? C14 C15 1.371(6) . ? C14 H14 0.9300 . ? C15 C16 1.384(6) . ? C15 H15 0.9300 . ? C16 N2 1.326(5) . ? C16 H16 0.9300 . ? C17 N2 1.347(5) . ? C17 C18 1.439(6) . ? C18 N1 1.354(5) . ? C19 O2 1.243(5) . ? C19 O1 1.287(5) . ? C19 C20 1.507(6) . ? C20 N5 1.514(5) . ? C20 C21 1.528(5) . ? C20 H20 0.9800 . ? C21 C22 1.503(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C29 1.359(7) . ? C22 C23 1.455(6) . ? C23 C24 1.391(6) . ? C23 C28 1.413(6) . ? C24 C25 1.373(7) . ? C24 H24 0.9300 . ? C25 C26 1.396(7) . ? C25 H25 0.9300 . ? C26 C27 1.405(10) . ? C26 H26 0.9300 . ? C27 C28 1.372(7) . ? C27 H27 0.9300 . ? C28 N6 1.387(6) . ? C29 N6 1.359(6) . ? C29 H29 0.9300 . ? C30 O7 1.433(7) . ? C30 O7' 1.474(10) . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N6 H6 0.8600 . ? N7 O6 1.215(5) . ? N7 O4 1.233(6) . ? N7 O5 1.256(6) . ? 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 N1 92.06(13) . . ? O1 Cu1 N5 84.93(15) . . ? N1 Cu1 N5 157.11(13) . . ? O1 Cu1 N2 173.73(13) . . ? N1 Cu1 N2 81.89(13) . . ? N5 Cu1 N2 99.99(15) . . ? O1 Cu1 O3 86.18(12) . . ? N1 Cu1 O3 103.43(12) . . ? N5 Cu1 O3 99.01(13) . . ? N2 Cu1 O3 96.80(12) . . ? N1 C1 C2 122.0(4) . . ? N1 C1 H1 119.0 . . ? C2 C1 H1 119.0 . . ? C3 C2 C1 119.8(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C18 C4 C3 117.6(4) . . ? C18 C4 C5 119.1(3) . . ? C3 C4 C5 123.3(4) . . ? N4 C5 C12 122.3(3) . . ? N4 C5 C4 118.2(4) . . ? C12 C5 C4 119.6(3) . . ? N4 C6 C7 119.5(6) . . ? N4 C6 C11 121.9(4) . . ? C7 C6 C11 118.6(4) . . ? C8 C7 C6 119.6(6) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 121.3(5) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 120.8(5) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.3(5) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? N3 C11 C10 119.4(4) . . ? N3 C11 C6 120.3(4) . . ? C10 C11 C6 120.3(4) . . ? N3 C12 C5 121.7(3) . . ? N3 C12 C13 118.1(4) . . ? C5 C12 C13 120.2(3) . . ? C17 C13 C14 117.1(3) . . ? C17 C13 C12 118.9(3) . . ? C14 C13 C12 124.0(3) . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 118.7(4) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N2 C16 C15 123.3(4) . . ? N2 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? N2 C17 C13 122.9(4) . . ? N2 C17 C18 116.3(4) . . ? C13 C17 C18 120.8(4) . . ? N1 C18 C4 122.9(3) . . ? N1 C18 C17 115.8(4) . . ? C4 C18 C17 121.3(4) . . ? O2 C19 O1 123.0(4) . . ? O2 C19 C20 118.8(4) . . ? O1 C19 C20 118.1(4) . . ? C19 C20 N5 109.1(3) . . ? C19 C20 C21 109.3(3) . . ? N5 C20 C21 110.3(3) . . ? C19 C20 H20 109.4 . . ? N5 C20 H20 109.4 . . ? C21 C20 H20 109.4 . . ? C22 C21 C20 114.4(3) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C29 C22 C23 105.7(4) . . ? C29 C22 C21 126.4(4) . . ? C23 C22 C21 127.8(4) . . ? C24 C23 C28 118.2(4) . . ? C24 C23 C22 134.7(4) . . ? C28 C23 C22 107.1(4) . . ? C25 C24 C23 119.4(4) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 121.7(5) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C25 C26 C27 120.3(5) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 117.1(5) . . ? C28 C27 H27 121.5 . . ? C26 C27 H27 121.5 . . ? C27 C28 N6 129.9(5) . . ? C27 C28 C23 123.4(5) . . ? N6 C28 C23 106.7(4) . . ? C22 C29 N6 111.2(4) . . ? C22 C29 H29 124.4 . . ? N6 C29 H29 124.4 . . ? O7 C30 O7' 109.2(5) . . ? C1 N1 C18 118.4(3) . . ? C1 N1 Cu1 128.3(3) . . ? C18 N1 Cu1 113.0(2) . . ? C16 N2 C17 118.1(3) . . ? C16 N2 Cu1 129.4(3) . . ? C17 N2 Cu1 112.4(3) . . ? C12 N3 C11 116.9(4) . . ? C5 N4 C6 116.9(4) . . ? C20 N5 Cu1 105.8(2) . . ? C20 N5 H5A 110.6 . . ? Cu1 N5 H5A 110.6 . . ? C20 N5 H5B 110.6 . . ? Cu1 N5 H5B 110.6 . . ? H5A N5 H5B 108.7 . . ? C29 N6 C28 109.2(4) . . ? C29 N6 H6 125.4 . . ? C28 N6 H6 125.4 . . ? O6 N7 O4 119.7(5) . . ? O6 N7 O5 122.5(6) . . ? O4 N7 O5 117.4(5) . . ? C19 O1 Cu1 114.0(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.957 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.104 # Attachment 'B802948B-cif2-revised.cif' data_arc2 _database_code_depnum_ccdc_archive 'CCDC 678817' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration rm _chemical_formula_moiety 'C27 H24 Cu N6 O7' _chemical_formula_sum 'C27 H24 Cu N6 O7' _chemical_formula_weight 608.06 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 P212121 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 6.939(2) _cell_length_b 25.837(8) _cell_length_c 30.520(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5472(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2504 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8475 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details SADABS(Sheldrick,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 'Bruker Smart CCD Area Detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42121 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10756 _reflns_number_gt 7538 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0882P)^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 0.038(19) _refine_ls_number_reflns 10756 _refine_ls_number_parameters 739 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.010 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 1.01489(10) 0.83379(2) 0.286206(19) 0.04831(19) Uani 1 1 d . . . Cu2 Cu 0.53516(11) 0.16086(2) 0.28171(2) 0.0523(2) Uani 1 1 d . . . C1 C 0.8779(8) 0.79310(19) 0.19932(18) 0.0485(14) Uani 1 1 d . . . H1 H 0.8903 0.7600 0.2110 0.058 Uiso 1 1 calc R . . C2 C 0.8252(9) 0.7979(2) 0.15630(18) 0.0526(15) Uani 1 1 d . . . H2 H 0.8048 0.7686 0.1391 0.063 Uiso 1 1 calc R . . C3 C 0.8028(8) 0.8468(2) 0.13884(17) 0.0469(13) Uani 1 1 d . . . H3 H 0.7643 0.8508 0.1099 0.056 Uiso 1 1 calc R . . C4 C 0.8385(7) 0.89041(18) 0.16509(16) 0.0390(12) Uani 1 1 d . . . C5 C 0.8270(7) 0.9430(2) 0.14897(17) 0.0414(12) Uani 1 1 d . . . C6 C 0.7770(8) 1.0003(2) 0.0934(2) 0.0455(15) Uani 1 1 d . . . C7 C 0.7354(10) 1.0107(2) 0.0488(2) 0.0655(19) Uani 1 1 d . . . H7 H 0.7193 0.9837 0.0291 0.079 Uiso 1 1 calc R . . C8 C 0.7192(11) 1.0607(3) 0.0352(2) 0.0710(19) Uani 1 1 d . . . H8 H 0.6922 1.0677 0.0059 0.085 Uiso 1 1 calc R . . C9 C 0.7426(10) 1.1013(3) 0.0646(2) 0.0690(19) Uani 1 1 d . . . H9 H 0.7281 1.1351 0.0546 0.083 Uiso 1 1 calc R . . C10 C 0.7855(9) 1.0934(2) 0.1070(2) 0.0572(15) Uani 1 1 d . . . H10 H 0.8035 1.1214 0.1256 0.069 Uiso 1 1 calc R . . C11 C 0.8034(8) 1.0420(2) 0.12319(19) 0.0456(14) Uani 1 1 d . . . C12 C 0.8586(7) 0.98510(18) 0.17860(18) 0.0391(12) Uani 1 1 d . . . C13 C 0.9060(7) 0.97511(18) 0.22433(17) 0.0399(12) Uani 1 1 d . . . C14 C 0.9339(8) 1.01388(19) 0.25577(19) 0.0475(14) Uani 1 1 d . . . H14 H 0.9230 1.0485 0.2479 0.057 Uiso 1 1 calc R . . C15 C 0.9773(9) 1.00056(17) 0.29816(18) 0.0493(14) Uani 1 1 d . . . H15 H 0.9930 1.0261 0.3194 0.059 Uiso 1 1 calc R . . C16 C 0.9973(9) 0.94912(19) 0.30899(15) 0.0492(13) Uani 1 1 d . . . H16 H 1.0313 0.9407 0.3376 0.059 Uiso 1 1 calc R . . C17 C 0.9244(8) 0.92448(18) 0.23813(17) 0.0412(13) Uani 1 1 d . . . C18 C 0.8928(7) 0.88157(18) 0.20846(16) 0.0372(11) Uani 1 1 d . . . C19 C 1.0987(8) 0.7397(2) 0.32139(18) 0.0484(14) Uani 1 1 d . . . C20 C 1.1659(9) 0.7766(2) 0.35724(17) 0.0488(14) Uani 1 1 d . . . H20 H 1.3070 0.7771 0.3565 0.059 Uiso 1 1 calc R . . C21 C 1.1068(11) 0.7577(2) 0.40218(17) 0.0711(19) Uani 1 1 d . . . H21A H 0.9675 0.7592 0.4044 0.085 Uiso 1 1 calc R . . H21B H 1.1450 0.7218 0.4052 0.085 Uiso 1 1 calc R . . C22 C 1.1927(10) 0.7882(2) 0.43938(19) 0.0589(16) Uani 1 1 d . . . C23 C 1.0957(11) 0.8261(3) 0.4605(2) 0.089(2) Uani 1 1 d . . . H23 H 0.9697 0.8334 0.4521 0.106 Uiso 1 1 calc R . . C24 C 1.1779(14) 0.8545(4) 0.4944(3) 0.112(3) Uani 1 1 d . . . H24 H 1.1059 0.8797 0.5087 0.135 Uiso 1 1 calc R . . C25 C 1.3598(15) 0.8457(4) 0.5063(3) 0.115(3) Uani 1 1 d . . . H25 H 1.4161 0.8651 0.5286 0.139 Uiso 1 1 calc R . . C26 C 1.4632(13) 0.8078(4) 0.4853(3) 0.114(3) Uani 1 1 d . . . H26 H 1.5894 0.8010 0.4937 0.137 Uiso 1 1 calc R . . C27 C 1.3802(12) 0.7797(3) 0.4515(2) 0.088(2) Uani 1 1 d . . . H27 H 1.4525 0.7548 0.4370 0.106 Uiso 1 1 calc R . . C28 C 0.4042(8) 0.2010(2) 0.19515(18) 0.0503(14) Uani 1 1 d . . . H28 H 0.4253 0.2341 0.2062 0.060 Uiso 1 1 calc R . . C29 C 0.3457(9) 0.1955(2) 0.1518(2) 0.0557(16) Uani 1 1 d . . . H29 H 0.3237 0.2247 0.1347 0.067 Uiso 1 1 calc R . . C30 C 0.3205(9) 0.1476(2) 0.13414(19) 0.0558(15) Uani 1 1 d . . . H30 H 0.2860 0.1438 0.1049 0.067 Uiso 1 1 calc R . . C31 C 0.3480(8) 0.1033(2) 0.16140(18) 0.0459(13) Uani 1 1 d . . . C32 C 0.3255(8) 0.0502(2) 0.14626(19) 0.0466(13) Uani 1 1 d . . . C33 C 0.2758(9) -0.0075(3) 0.0912(2) 0.0571(17) Uani 1 1 d . . . C34 C 0.2366(10) -0.0183(3) 0.0469(2) 0.0692(19) Uani 1 1 d . . . H34 H 0.2110 0.0083 0.0272 0.083 Uiso 1 1 calc R . . C35 C 0.2371(12) -0.0683(3) 0.0335(3) 0.083(2) Uani 1 1 d . . . H35 H 0.2156 -0.0758 0.0041 0.100 Uiso 1 1 calc R . . C36 C 0.2689(12) -0.1085(3) 0.0627(3) 0.086(2) Uani 1 1 d . . . H36 H 0.2657 -0.1424 0.0524 0.103 Uiso 1 1 calc R . . C37 C 0.3049(10) -0.1000(2) 0.1061(2) 0.0702(19) Uani 1 1 d . . . H37 H 0.3264 -0.1275 0.1251 0.084 Uiso 1 1 calc R . . C38 C 0.3085(9) -0.0493(3) 0.1210(2) 0.0559(16) Uani 1 1 d . . . C39 C 0.3580(8) 0.0083(2) 0.1764(2) 0.0495(15) Uani 1 1 d . . . C40 C 0.4062(7) 0.01905(18) 0.22183(19) 0.0427(13) Uani 1 1 d . . . C41 C 0.4288(8) -0.0192(2) 0.2531(2) 0.0493(14) Uani 1 1 d . . . H41 H 0.4119 -0.0538 0.2456 0.059 Uiso 1 1 calc R . . C42 C 0.4764(9) -0.0058(2) 0.2957(2) 0.0581(16) Uani 1 1 d . . . H42 H 0.4912 -0.0311 0.3171 0.070 Uiso 1 1 calc R . . C43 C 0.5018(9) 0.0461(2) 0.30571(17) 0.0546(14) Uani 1 1 d . . . H43 H 0.5342 0.0548 0.3343 0.066 Uiso 1 1 calc R . . C44 C 0.4312(7) 0.07044(19) 0.23540(17) 0.0426(13) Uani 1 1 d . . . C45 C 0.4002(8) 0.11301(19) 0.20386(18) 0.0437(13) Uani 1 1 d . . . C46 C 0.6154(9) 0.2554(2) 0.3171(2) 0.0522(15) Uani 1 1 d . . . C47 C 0.6121(9) 0.2198(2) 0.35794(18) 0.0521(15) Uani 1 1 d . . . H47 H 0.4864 0.2245 0.3721 0.063 Uiso 1 1 calc R . . C48 C 0.7638(9) 0.2343(2) 0.39128(19) 0.0630(16) Uani 1 1 d . . . H48A H 0.8898 0.2259 0.3795 0.076 Uiso 1 1 calc R . . H48B H 0.7593 0.2714 0.3961 0.076 Uiso 1 1 calc R . . C49 C 0.7393(9) 0.2073(2) 0.43434(18) 0.0547(15) Uani 1 1 d . . . C50 C 0.5936(13) 0.2212(3) 0.4626(3) 0.095(2) Uani 1 1 d . . . H50 H 0.5110 0.2480 0.4547 0.114 Uiso 1 1 calc R . . C51 C 0.5661(17) 0.1966(4) 0.5028(3) 0.124(4) Uani 1 1 d . . . H51 H 0.4757 0.2089 0.5227 0.149 Uiso 1 1 calc R . . C52 C 0.6732(18) 0.1546(5) 0.5120(3) 0.121(4) Uani 1 1 d . . . H52 H 0.6472 0.1352 0.5369 0.145 Uiso 1 1 calc R . . C53 C 0.8160(16) 0.1409(4) 0.4855(3) 0.116(3) Uani 1 1 d . . . H53 H 0.8954 0.1134 0.4933 0.139 Uiso 1 1 calc R . . C54 C 0.8487(11) 0.1664(3) 0.4471(2) 0.083(2) Uani 1 1 d . . . H54 H 0.9490 0.1555 0.4292 0.100 Uiso 1 1 calc R . . N1 N 0.9125(6) 0.83350(15) 0.22547(13) 0.0450(10) Uani 1 1 d . . . N2 N 0.9702(6) 0.91088(15) 0.28030(13) 0.0460(10) Uani 1 1 d . . . N3 N 0.7888(6) 0.95101(17) 0.10694(15) 0.0470(11) Uani 1 1 d . . . N4 N 0.8459(7) 1.03359(16) 0.16569(15) 0.0449(11) Uani 1 1 d . . . N5 N 1.0995(7) 0.82936(16) 0.34845(13) 0.0478(11) Uani 1 1 d . . . H5A H 1.1958 0.8520 0.3534 0.057 Uiso 1 1 calc R . . H5B H 1.0008 0.8373 0.3663 0.057 Uiso 1 1 calc R . . N6 N 0.4305(6) 0.16110(15) 0.22096(14) 0.0486(10) Uani 1 1 d . . . N7 N 0.4823(7) 0.08390(15) 0.27672(13) 0.0473(11) Uani 1 1 d . . . N8 N 0.2843(7) 0.0424(2) 0.10465(15) 0.0522(12) Uani 1 1 d . . . N9 N 0.3481(7) -0.04026(18) 0.16334(16) 0.0519(12) Uani 1 1 d . . . N10 N 0.6219(7) 0.16585(17) 0.34349(13) 0.0522(12) Uani 1 1 d . . . H10A H 0.5462 0.1461 0.3606 0.063 Uiso 1 1 calc R . . H10B H 0.7437 0.1542 0.3458 0.063 Uiso 1 1 calc R . . N11 N 0.6103(10) 0.8627(2) 0.3594(2) 0.0773(17) Uani 1 1 d . . . N12 N 0.1424(9) 0.1359(2) 0.3495(2) 0.0684(16) Uani 1 1 d . . . O1 O 1.0143(6) 0.75973(12) 0.28822(11) 0.0527(9) Uani 1 1 d . . . O2 O 1.1306(7) 0.69314(14) 0.32520(12) 0.0654(12) Uani 1 1 d . . . O3 O 1.3327(6) 0.84955(14) 0.26067(13) 0.0609(11) Uani 1 1 d . . . O4 O 0.5645(6) 0.23464(13) 0.28107(12) 0.0580(10) Uani 1 1 d . . . O5 O 0.6556(7) 0.30144(15) 0.32136(13) 0.0660(12) Uani 1 1 d . . . O6 O 0.8556(6) 0.14340(14) 0.25463(13) 0.0601(11) Uani 1 1 d . . . O7 O 0.4602(7) 0.88795(19) 0.36160(19) 0.0929(16) Uani 1 1 d . . . O8 O 0.7417(9) 0.8739(3) 0.38536(18) 0.114(2) Uani 1 1 d . . . O9 O 0.6321(8) 0.8296(2) 0.3314(2) 0.110(2) Uani 1 1 d . . . O10 O 0.1706(8) 0.1674(2) 0.32197(19) 0.0946(17) Uani 1 1 d . . . O11 O 0.2650(9) 0.1265(3) 0.37927(19) 0.124(2) Uani 1 1 d . . . O12 O -0.0096(8) 0.10897(16) 0.35102(17) 0.0861(14) Uani 1 1 d . . . OW1 O 0.569(6) -0.0220(4) 0.4233(4) 0.79(3) Uani 1 1 d . . . OW2 O 1.128(7) 1.0207(5) 0.4193(4) 0.78(3) 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 0.0600(4) 0.0370(3) 0.0479(4) -0.0044(3) -0.0084(4) -0.0008(3) Cu2 0.0639(4) 0.0414(3) 0.0515(4) 0.0071(3) -0.0036(4) 0.0028(3) C1 0.051(3) 0.033(3) 0.061(4) -0.005(3) 0.002(3) -0.001(2) C2 0.057(4) 0.050(3) 0.052(3) -0.018(3) -0.007(3) -0.008(3) C3 0.047(3) 0.049(3) 0.044(3) -0.006(3) -0.007(3) -0.004(3) C4 0.032(3) 0.033(2) 0.051(3) -0.010(2) 0.009(3) -0.002(2) C5 0.031(3) 0.046(3) 0.047(3) -0.004(3) -0.001(3) 0.003(2) C6 0.031(3) 0.055(4) 0.051(4) 0.000(3) 0.005(3) 0.004(3) C7 0.062(4) 0.066(4) 0.068(5) 0.010(3) -0.012(4) 0.003(3) C8 0.076(5) 0.076(5) 0.061(4) 0.009(4) -0.006(4) 0.003(4) C9 0.056(4) 0.068(4) 0.083(5) 0.018(4) 0.006(4) 0.008(3) C10 0.048(4) 0.050(3) 0.074(4) 0.001(3) 0.009(3) -0.005(3) C11 0.029(3) 0.049(3) 0.058(4) 0.000(3) 0.009(3) 0.006(2) C12 0.028(3) 0.034(3) 0.055(3) 0.000(2) 0.002(3) 0.002(2) C13 0.034(3) 0.039(3) 0.046(3) -0.006(2) 0.003(3) 0.005(2) C14 0.043(3) 0.031(2) 0.068(4) -0.007(2) 0.006(3) 0.002(2) C15 0.057(4) 0.041(3) 0.050(3) -0.016(2) -0.008(3) -0.007(3) C16 0.062(4) 0.051(3) 0.035(3) -0.009(2) -0.003(3) -0.003(3) C17 0.035(3) 0.038(3) 0.051(3) -0.005(2) 0.005(3) -0.004(2) C18 0.032(3) 0.044(3) 0.036(3) -0.005(2) -0.002(2) 0.002(2) C19 0.052(4) 0.047(3) 0.046(3) 0.002(3) 0.003(3) -0.004(3) C20 0.054(4) 0.051(3) 0.042(3) 0.001(3) -0.001(3) -0.004(3) C21 0.100(5) 0.067(4) 0.047(3) 0.007(3) -0.006(4) -0.023(4) C22 0.066(4) 0.065(4) 0.046(3) 0.007(3) 0.001(3) -0.011(3) C23 0.062(4) 0.116(6) 0.089(5) -0.020(5) -0.010(4) 0.001(4) C24 0.084(7) 0.154(9) 0.099(6) -0.058(6) -0.006(5) 0.010(6) C25 0.100(7) 0.165(9) 0.081(6) -0.053(6) -0.010(5) -0.007(7) C26 0.072(5) 0.192(10) 0.079(5) -0.020(6) -0.022(5) 0.017(6) C27 0.083(5) 0.120(6) 0.062(4) -0.009(4) -0.013(4) 0.027(5) C28 0.049(3) 0.044(3) 0.058(4) 0.010(3) -0.001(3) 0.009(3) C29 0.047(3) 0.053(3) 0.067(4) 0.016(3) -0.001(3) 0.007(3) C30 0.046(3) 0.066(4) 0.056(3) 0.014(3) 0.001(3) 0.009(3) C31 0.035(3) 0.050(3) 0.052(3) 0.000(3) -0.003(3) 0.005(3) C32 0.029(3) 0.054(3) 0.057(4) 0.000(3) 0.005(3) 0.000(2) C33 0.040(3) 0.065(4) 0.067(5) -0.011(3) 0.005(3) 0.002(3) C34 0.063(5) 0.082(5) 0.063(5) -0.005(4) -0.005(4) -0.001(4) C35 0.078(5) 0.092(6) 0.079(5) -0.026(5) -0.005(5) -0.004(4) C36 0.088(6) 0.069(5) 0.101(6) -0.015(4) 0.000(5) 0.003(4) C37 0.065(4) 0.059(4) 0.086(5) -0.014(4) -0.007(4) -0.007(3) C38 0.037(3) 0.061(4) 0.070(4) -0.007(3) 0.006(3) 0.000(3) C39 0.029(3) 0.046(3) 0.074(4) 0.008(3) 0.008(3) 0.002(2) C40 0.027(3) 0.039(3) 0.062(4) 0.007(3) 0.009(3) 0.001(2) C41 0.037(3) 0.040(3) 0.071(4) 0.006(3) 0.006(3) -0.005(3) C42 0.050(4) 0.052(3) 0.072(4) 0.021(3) 0.015(4) -0.001(3) C43 0.056(4) 0.050(3) 0.058(3) 0.015(3) -0.005(3) -0.003(3) C44 0.030(3) 0.048(3) 0.050(3) 0.011(2) 0.002(3) 0.000(2) C45 0.036(3) 0.040(3) 0.055(3) 0.006(3) 0.009(3) 0.002(2) C46 0.056(4) 0.046(3) 0.055(4) 0.005(3) 0.012(3) 0.003(3) C47 0.051(4) 0.050(3) 0.055(3) 0.010(3) 0.008(3) 0.002(3) C48 0.066(4) 0.064(4) 0.059(4) 0.007(3) 0.002(3) -0.012(3) C49 0.058(4) 0.065(4) 0.041(3) -0.006(3) 0.005(3) -0.010(3) C50 0.095(6) 0.089(5) 0.102(6) 0.003(5) 0.019(5) 0.003(5) C51 0.156(10) 0.140(8) 0.077(6) -0.012(6) 0.061(6) -0.004(8) C52 0.150(10) 0.161(10) 0.052(5) 0.018(6) -0.008(6) -0.031(8) C53 0.124(9) 0.150(9) 0.074(6) 0.022(6) -0.012(6) 0.018(7) C54 0.083(5) 0.107(6) 0.059(4) 0.002(4) 0.002(4) 0.014(5) N1 0.047(2) 0.038(2) 0.050(2) -0.006(2) -0.003(2) -0.002(2) N2 0.046(3) 0.040(2) 0.051(3) -0.009(2) 0.003(3) -0.001(2) N3 0.044(3) 0.045(3) 0.052(3) 0.000(2) 0.002(2) 0.006(2) N4 0.038(3) 0.041(2) 0.055(3) 0.000(2) 0.007(2) 0.002(2) N5 0.050(3) 0.046(2) 0.047(3) -0.006(2) 0.002(2) -0.002(2) N6 0.049(2) 0.040(2) 0.057(3) 0.009(2) 0.003(2) 0.003(2) N7 0.048(3) 0.045(2) 0.049(3) 0.006(2) 0.003(3) 0.004(2) N8 0.040(3) 0.067(3) 0.049(3) 0.002(3) 0.000(2) 0.000(2) N9 0.042(3) 0.049(3) 0.064(3) -0.001(2) 0.004(3) -0.006(2) N10 0.056(3) 0.050(3) 0.051(3) 0.005(2) 0.008(2) 0.007(2) N11 0.062(4) 0.076(4) 0.094(5) 0.010(4) -0.014(4) -0.015(4) N12 0.046(3) 0.065(4) 0.094(5) -0.027(3) -0.002(3) 0.009(3) O1 0.070(2) 0.0380(16) 0.050(2) -0.0008(16) -0.006(2) -0.0062(18) O2 0.097(4) 0.043(2) 0.057(2) 0.0043(19) -0.003(2) 0.012(2) O3 0.062(3) 0.055(2) 0.066(3) -0.009(2) 0.010(2) -0.004(2) O4 0.079(3) 0.0406(18) 0.054(2) 0.0040(18) -0.001(2) 0.0015(18) O5 0.088(3) 0.046(2) 0.063(3) 0.007(2) -0.001(2) -0.003(2) O6 0.063(3) 0.050(2) 0.067(2) 0.0070(19) 0.007(2) 0.001(2) O7 0.056(3) 0.080(3) 0.142(5) 0.010(3) -0.017(3) 0.007(3) O8 0.075(4) 0.178(6) 0.089(4) -0.032(4) -0.016(3) 0.023(4) O9 0.084(4) 0.080(4) 0.165(6) -0.037(4) -0.027(4) -0.001(3) O10 0.080(4) 0.072(3) 0.132(5) 0.025(3) -0.012(3) 0.010(3) O11 0.064(4) 0.218(8) 0.090(4) 0.014(4) 0.000(4) -0.017(4) O12 0.080(4) 0.057(2) 0.122(4) -0.020(3) -0.008(3) -0.002(3) OW1 2.00(11) 0.129(9) 0.227(13) -0.083(9) -0.37(3) 0.09(3) OW2 2.00(11) 0.199(12) 0.155(10) 0.019(9) 0.02(3) 0.12(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 1.914(3) . ? Cu1 N1 1.985(4) . ? Cu1 N5 1.992(4) . ? Cu1 N2 2.024(4) . ? Cu1 O3 2.374(4) . ? Cu2 O4 1.917(3) . ? Cu2 N10 1.983(4) . ? Cu2 N6 1.991(4) . ? Cu2 N7 2.028(4) . ? Cu2 O6 2.415(4) . ? C1 N1 1.336(6) . ? C1 C2 1.368(7) . ? C1 H1 0.9300 . ? C2 C3 1.381(7) . ? C2 H2 0.9300 . ? C3 C4 1.405(6) . ? C3 H3 0.9300 . ? C4 C18 1.395(7) . ? C4 C5 1.446(7) . ? C5 N3 1.326(7) . ? C5 C12 1.432(7) . ? C6 N3 1.341(6) . ? C6 C7 1.415(9) . ? C6 C11 1.423(8) . ? C7 C8 1.361(8) . ? C7 H7 0.9300 . ? C8 C9 1.391(9) . ? C8 H8 0.9300 . ? C9 C10 1.342(8) . ? C9 H9 0.9300 . ? C10 C11 1.422(8) . ? C10 H10 0.9300 . ? C11 N4 1.348(7) . ? C12 N4 1.316(6) . ? C12 C13 1.457(7) . ? C13 C17 1.380(6) . ? C13 C14 1.400(7) . ? C14 C15 1.372(7) . ? C14 H14 0.9300 . ? C15 C16 1.377(6) . ? C15 H15 0.9300 . ? C16 N2 1.333(6) . ? C16 H16 0.9300 . ? C17 N2 1.372(6) . ? C17 C18 1.448(6) . ? C18 N1 1.353(6) . ? C19 O2 1.229(6) . ? C19 O1 1.279(6) . ? C19 C20 1.524(7) . ? C20 N5 1.465(6) . ? C20 C21 1.512(7) . ? C20 H20 0.9800 . ? C21 C22 1.505(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.351(9) . ? C22 C27 1.371(10) . ? C23 C24 1.390(10) . ? C23 H23 0.9300 . ? C24 C25 1.333(12) . ? C24 H24 0.9300 . ? C25 C26 1.373(11) . ? C25 H25 0.9300 . ? C26 C27 1.385(10) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 N6 1.311(6) . ? C28 C29 1.392(8) . ? C28 H28 0.9300 . ? C29 C30 1.359(8) . ? C29 H29 0.9300 . ? C30 C31 1.428(7) . ? C30 H30 0.9300 . ? C31 C45 1.369(7) . ? C31 C32 1.457(8) . ? C32 N8 1.318(7) . ? C32 C39 1.437(8) . ? C33 N8 1.355(7) . ? C33 C34 1.406(9) . ? C33 C38 1.431(9) . ? C34 C35 1.355(9) . ? C34 H34 0.9300 . ? C35 C36 1.385(10) . ? C35 H35 0.9300 . ? C36 C37 1.365(9) . ? C36 H36 0.9300 . ? C37 C38 1.387(8) . ? C37 H37 0.9300 . ? C38 N9 1.340(7) . ? C39 N9 1.319(7) . ? C39 C40 1.453(8) . ? C40 C41 1.385(7) . ? C40 C44 1.402(7) . ? C41 C42 1.384(8) . ? C41 H41 0.9300 . ? C42 C43 1.385(7) . ? C42 H42 0.9300 . ? C43 N7 1.326(6) . ? C43 H43 0.9300 . ? C44 N7 1.355(6) . ? C44 C45 1.477(7) . ? C45 N6 1.364(6) . ? C46 O5 1.229(6) . ? C46 O4 1.273(6) . ? C46 C47 1.549(7) . ? C47 N10 1.464(7) . ? C47 C48 1.511(8) . ? C47 H47 0.9800 . ? C48 C49 1.498(8) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 C54 1.357(9) . ? C49 C50 1.377(9) . ? C50 C51 1.395(10) . ? C50 H50 0.9300 . ? C51 C52 1.344(13) . ? C51 H51 0.9300 . ? C52 C53 1.326(13) . ? C52 H52 0.9300 . ? C53 C54 1.364(10) . ? C53 H53 0.9300 . ? C54 H54 0.9300 . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N10 H10A 0.9000 . ? N10 H10B 0.9000 . ? N11 O9 1.218(7) . ? N11 O7 1.231(8) . ? N11 O8 1.242(7) . ? N12 O10 1.185(7) . ? N12 O12 1.265(7) . ? N12 O11 1.269(8) . ? 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 N1 91.46(15) . . ? O1 Cu1 N5 84.98(16) . . ? N1 Cu1 N5 174.84(18) . . ? O1 Cu1 N2 170.48(18) . . ? N1 Cu1 N2 82.29(16) . . ? N5 Cu1 N2 100.76(17) . . ? O1 Cu1 O3 100.59(16) . . ? N1 Cu1 O3 91.51(16) . . ? N5 Cu1 O3 92.81(17) . . ? N2 Cu1 O3 86.80(16) . . ? O4 Cu2 N10 85.00(17) . . ? O4 Cu2 N6 91.50(16) . . ? N10 Cu2 N6 174.63(18) . . ? O4 Cu2 N7 173.45(18) . . ? N10 Cu2 N7 100.96(18) . . ? N6 Cu2 N7 82.36(16) . . ? O4 Cu2 O6 94.85(16) . . ? N10 Cu2 O6 93.33(17) . . ? N6 Cu2 O6 91.01(16) . . ? N7 Cu2 O6 87.57(16) . . ? N1 C1 C2 123.4(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.9(5) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 119.6(5) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C18 C4 C3 117.2(5) . . ? C18 C4 C5 119.4(4) . . ? C3 C4 C5 123.3(5) . . ? N3 C5 C12 121.5(5) . . ? N3 C5 C4 119.2(5) . . ? C12 C5 C4 119.4(5) . . ? N3 C6 C7 119.4(5) . . ? N3 C6 C11 120.9(6) . . ? C7 C6 C11 119.7(5) . . ? C8 C7 C6 119.5(6) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.5(7) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 122.2(6) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 119.8(6) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N4 C11 C10 120.3(5) . . ? N4 C11 C6 121.4(5) . . ? C10 C11 C6 118.2(6) . . ? N4 C12 C5 121.6(5) . . ? N4 C12 C13 118.1(5) . . ? C5 C12 C13 120.3(4) . . ? C17 C13 C14 117.1(5) . . ? C17 C13 C12 118.7(4) . . ? C14 C13 C12 124.1(5) . . ? C15 C14 C13 119.8(5) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 119.4(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? N2 C16 C15 122.9(5) . . ? N2 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? N2 C17 C13 123.4(4) . . ? N2 C17 C18 115.2(4) . . ? C13 C17 C18 121.4(5) . . ? N1 C18 C4 122.8(4) . . ? N1 C18 C17 116.6(4) . . ? C4 C18 C17 120.6(4) . . ? O2 C19 O1 123.6(5) . . ? O2 C19 C20 119.3(5) . . ? O1 C19 C20 117.1(5) . . ? N5 C20 C21 112.4(5) . . ? N5 C20 C19 110.8(4) . . ? C21 C20 C19 111.6(5) . . ? N5 C20 H20 107.3 . . ? C21 C20 H20 107.3 . . ? C19 C20 H20 107.3 . . ? C22 C21 C20 114.1(5) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C27 117.4(6) . . ? C23 C22 C21 122.8(7) . . ? C27 C22 C21 119.7(7) . . ? C22 C23 C24 122.2(8) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C25 C24 C23 120.2(9) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.2(8) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C25 C26 C27 120.2(8) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C22 C27 C26 120.8(7) . . ? C22 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? N6 C28 C29 122.0(5) . . ? N6 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? C30 C29 C28 120.5(5) . . ? C30 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C29 C30 C31 118.8(5) . . ? C29 C30 H30 120.6 . . ? C31 C30 H30 120.6 . . ? C45 C31 C30 116.1(5) . . ? C45 C31 C32 120.1(5) . . ? C30 C31 C32 123.8(5) . . ? N8 C32 C39 122.4(6) . . ? N8 C32 C31 118.2(5) . . ? C39 C32 C31 119.3(5) . . ? N8 C33 C34 119.2(7) . . ? N8 C33 C38 121.2(6) . . ? C34 C33 C38 119.6(6) . . ? C35 C34 C33 118.5(7) . . ? C35 C34 H34 120.8 . . ? C33 C34 H34 120.8 . . ? C34 C35 C36 121.5(7) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C37 C36 C35 122.1(7) . . ? C37 C36 H36 118.9 . . ? C35 C36 H36 118.9 . . ? C36 C37 C38 118.3(7) . . ? C36 C37 H37 120.8 . . ? C38 C37 H37 120.8 . . ? N9 C38 C37 119.0(6) . . ? N9 C38 C33 120.9(6) . . ? C37 C38 C33 120.0(6) . . ? N9 C39 C32 120.9(6) . . ? N9 C39 C40 118.8(5) . . ? C32 C39 C40 120.2(5) . . ? C41 C40 C44 117.3(5) . . ? C41 C40 C39 123.2(5) . . ? C44 C40 C39 119.4(5) . . ? C42 C41 C40 119.6(5) . . ? C42 C41 H41 120.2 . . ? C40 C41 H41 120.2 . . ? C41 C42 C43 118.8(5) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? N7 C43 C42 123.5(5) . . ? N7 C43 H43 118.2 . . ? C42 C43 H43 118.2 . . ? N7 C44 C40 123.4(4) . . ? N7 C44 C45 117.0(4) . . ? C40 C44 C45 119.6(5) . . ? N6 C45 C31 124.8(5) . . ? N6 C45 C44 114.0(5) . . ? C31 C45 C44 121.3(5) . . ? O5 C46 O4 124.2(5) . . ? O5 C46 C47 119.5(5) . . ? O4 C46 C47 116.2(5) . . ? N10 C47 C48 114.0(5) . . ? N10 C47 C46 108.8(4) . . ? C48 C47 C46 112.6(5) . . ? N10 C47 H47 107.0 . . ? C48 C47 H47 107.0 . . ? C46 C47 H47 107.0 . . ? C49 C48 C47 113.4(5) . . ? C49 C48 H48A 108.9 . . ? C47 C48 H48A 108.9 . . ? C49 C48 H48B 108.9 . . ? C47 C48 H48B 108.9 . . ? H48A C48 H48B 107.7 . . ? C54 C49 C50 115.7(6) . . ? C54 C49 C48 123.4(6) . . ? C50 C49 C48 120.7(6) . . ? C49 C50 C51 122.1(8) . . ? C49 C50 H50 119.0 . . ? C51 C50 H50 119.0 . . ? C52 C51 C50 118.5(9) . . ? C52 C51 H51 120.8 . . ? C50 C51 H51 120.8 . . ? C53 C52 C51 120.0(9) . . ? C53 C52 H52 120.0 . . ? C51 C52 H52 120.0 . . ? C52 C53 C54 121.3(10) . . ? C52 C53 H53 119.4 . . ? C54 C53 H53 119.4 . . ? C49 C54 C53 122.0(8) . . ? C49 C54 H54 119.0 . . ? C53 C54 H54 119.0 . . ? C1 N1 C18 118.0(4) . . ? C1 N1 Cu1 128.7(4) . . ? C18 N1 Cu1 113.0(3) . . ? C16 N2 C17 117.3(4) . . ? C16 N2 Cu1 130.5(4) . . ? C17 N2 Cu1 111.8(3) . . ? C5 N3 C6 117.4(5) . . ? C12 N4 C11 117.2(5) . . ? C20 N5 Cu1 108.7(3) . . ? C20 N5 H5A 109.9 . . ? Cu1 N5 H5A 109.9 . . ? C20 N5 H5B 109.9 . . ? Cu1 N5 H5B 109.9 . . ? H5A N5 H5B 108.3 . . ? C28 N6 C45 117.8(5) . . ? C28 N6 Cu2 127.8(4) . . ? C45 N6 Cu2 114.2(3) . . ? C43 N7 C44 117.3(4) . . ? C43 N7 Cu2 130.9(4) . . ? C44 N7 Cu2 111.7(3) . . ? C32 N8 C33 116.5(5) . . ? C39 N9 C38 117.9(5) . . ? C47 N10 Cu2 109.5(3) . . ? C47 N10 H10A 109.8 . . ? Cu2 N10 H10A 109.8 . . ? C47 N10 H10B 109.8 . . ? Cu2 N10 H10B 109.8 . . ? H10A N10 H10B 108.2 . . ? O9 N11 O7 121.1(7) . . ? O9 N11 O8 121.3(7) . . ? O7 N11 O8 117.6(7) . . ? O10 N12 O12 122.8(7) . . ? O10 N12 O11 121.9(7) . . ? O12 N12 O11 115.3(7) . . ? C19 O1 Cu1 115.4(3) . . ? C46 O4 Cu2 116.0(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 0.645 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.091