# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Cuacac-R3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H17 Cu N5 O6' _chemical_formula_weight 522.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.4230(19) _cell_length_b 24.454(5) _cell_length_c 9.2950(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.96(3) _cell_angle_gamma 90.00 _cell_volume 2139.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3302 _cell_measurement_theta_min 1.07 _cell_measurement_theta_max 25.89 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 1.242 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.761 _exptl_absorpt_correction_T_max 0.807 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.75000 _diffrn_radiation_type synchrotron _diffrn_measurement_device_type 'MarCCD 165 detector' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5902 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.85 _reflns_number_total 3302 _reflns_number_gt 2904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Mar CCD' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _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. The restaints were listed here: DELU 0.002 O4 N5 ISOR 0.002 C18 N3 O6 ; _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^)+(0.0975P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3302 _refine_ls_number_parameters 318 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.005 _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 0.96657(3) 0.067717(12) 0.69644(3) 0.02511(17) Uani 1 1 d . . . N1 N 0.8202(2) 0.05215(9) 0.5352(2) 0.0228(5) Uani 1 1 d . . . N2 N 0.9596(2) -0.01411(9) 0.7177(2) 0.0250(5) Uani 1 1 d . . . N3 N 0.6526(2) -0.16388(8) 0.5281(2) 0.0262(5) Uani 1 1 d U . . O6 O 0.5406(2) -0.10741(7) 0.3695(2) 0.0296(5) Uani 1 1 d U . . N4 N 0.2785(3) -0.28610(10) 0.2651(3) 0.0382(6) Uani 1 1 d . . . N5 N 0.7228(2) 0.06272(8) 0.9015(2) 0.0181(5) Uani 1 1 d U . . O1 O 1.1293(2) 0.07087(7) 0.8300(2) 0.0325(5) Uani 1 1 d . . . O2 O 0.9885(2) 0.14170(7) 0.6303(2) 0.0284(4) Uani 1 1 d . . . O3 O 0.8243(2) 0.08993(8) 0.8695(2) 0.0355(5) Uani 1 1 d . . . O4 O 0.6849(2) 0.01998(10) 0.8343(2) 0.0491(6) Uani 1 1 d U . . O5 O 0.6548(3) 0.07452(9) 1.0116(3) 0.0441(6) Uani 1 1 d U . . C1 C 1.3192(3) 0.10662(14) 0.9766(4) 0.0442(8) Uani 1 1 d . . . H1A H 1.2989 0.0749 1.0366 0.066 Uiso 1 1 calc R . . H1B H 1.3274 0.1394 1.0371 0.066 Uiso 1 1 calc R . . H1C H 1.4086 0.1007 0.9296 0.066 Uiso 1 1 calc R . . C2 C 1.2001(3) 0.11418(12) 0.8635(3) 0.0313(7) Uani 1 1 d . . . C3 C 1.1771(3) 0.16525(12) 0.7988(3) 0.0329(7) Uani 1 1 d . . . H3 H 1.2329 0.1950 0.8353 0.039 Uiso 1 1 calc R . . C4 C 1.0785(3) 0.17591(11) 0.6848(3) 0.0292(6) Uani 1 1 d . . . C5 C 1.0757(3) 0.23136(11) 0.6130(4) 0.0369(7) Uani 1 1 d . . . H5A H 1.0724 0.2267 0.5081 0.055 Uiso 1 1 calc R . . H5B H 1.1615 0.2518 0.6437 0.055 Uiso 1 1 calc R . . H5C H 0.9915 0.2516 0.6405 0.055 Uiso 1 1 calc R . . C6 C 0.7541(3) 0.08741(10) 0.4452(3) 0.0235(6) Uani 1 1 d . . . H6 H 0.7797 0.1250 0.4503 0.028 Uiso 1 1 calc R . . C7 C 0.6481(3) 0.07081(10) 0.3434(3) 0.0242(6) Uani 1 1 d . . . H7 H 0.6048 0.0970 0.2796 0.029 Uiso 1 1 calc R . . C8 C 0.6061(3) 0.01698(11) 0.3351(3) 0.0245(6) Uani 1 1 d . . . H8 H 0.5340 0.0055 0.2665 0.029 Uiso 1 1 calc R . . C9 C 0.7808(3) -0.00161(10) 0.5293(3) 0.0217(6) Uani 1 1 d . . . C10 C 0.6732(3) -0.02067(10) 0.4315(3) 0.0221(6) Uani 1 1 d . . . C11 C 0.8575(3) -0.03774(10) 0.6297(3) 0.0233(6) Uani 1 1 d . . . C12 C 1.0339(3) -0.04520(13) 0.8124(3) 0.0292(7) Uani 1 1 d . . . H12 H 1.1042 -0.0285 0.8749 0.035 Uiso 1 1 calc R . . C13 C 1.0113(3) -0.10190(11) 0.8226(3) 0.0315(7) Uani 1 1 d . . . H13 H 1.0673 -0.1232 0.8895 0.038 Uiso 1 1 calc R . . C14 C 0.9084(3) -0.12606(11) 0.7360(3) 0.0311(7) Uani 1 1 d . . . H14 H 0.8922 -0.1643 0.7419 0.037 Uiso 1 1 calc R . . C15 C 0.8258(3) -0.09364(10) 0.6369(3) 0.0257(6) Uani 1 1 d . . . C16 C 0.7121(3) -0.11221(10) 0.5414(3) 0.0245(6) Uani 1 1 d . . . C17 C 0.6420(3) -0.07784(10) 0.4445(3) 0.0245(6) Uani 1 1 d . . . C18 C 0.5531(3) -0.15880(11) 0.4269(3) 0.0305(6) Uani 1 1 d U . . C19 C 0.4591(3) -0.20191(10) 0.3687(3) 0.0267(6) Uani 1 1 d . . . C20 C 0.3542(3) -0.19192(12) 0.2630(3) 0.0369(7) Uani 1 1 d . . . H20 H 0.3409 -0.1563 0.2236 0.044 Uiso 1 1 calc R . . C21 C 0.2678(3) -0.23533(13) 0.2151(4) 0.0417(8) Uani 1 1 d . . . H21 H 0.1964 -0.2280 0.1416 0.050 Uiso 1 1 calc R . . C22 C 0.3802(4) -0.29494(12) 0.3690(3) 0.0397(8) Uani 1 1 d . . . H22 H 0.3900 -0.3309 0.4072 0.048 Uiso 1 1 calc R . . C23 C 0.4716(3) -0.25498(11) 0.4239(3) 0.0351(7) Uani 1 1 d . . . H23 H 0.5417 -0.2634 0.4977 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0290(3) 0.0211(2) 0.0246(3) 0.00004(11) -0.00433(17) -0.00027(12) N1 0.0280(12) 0.0196(10) 0.0213(11) 0.0011(9) 0.0051(10) 0.0032(9) N2 0.0255(13) 0.0266(12) 0.0230(12) 0.0003(9) 0.0013(10) 0.0037(9) N3 0.0272(11) 0.0208(10) 0.0313(11) -0.0033(8) 0.0083(9) -0.0013(8) O6 0.0284(10) 0.0257(9) 0.0351(10) -0.0024(8) 0.0061(8) -0.0011(7) N4 0.0393(15) 0.0376(14) 0.0379(14) -0.0042(11) 0.0029(12) -0.0122(11) N5 0.0141(11) 0.0240(10) 0.0152(10) -0.0038(8) -0.0074(8) 0.0102(8) O1 0.0304(12) 0.0343(12) 0.0320(12) 0.0004(8) -0.0052(10) -0.0004(8) O2 0.0319(11) 0.0237(9) 0.0294(11) -0.0032(8) -0.0003(9) -0.0043(8) O3 0.0393(13) 0.0321(11) 0.0351(12) -0.0010(9) 0.0016(10) 0.0030(9) O4 0.0433(14) 0.0587(14) 0.0456(13) -0.0216(10) 0.0062(11) -0.0139(11) O5 0.0432(14) 0.0511(13) 0.0395(13) -0.0110(9) 0.0150(11) -0.0006(10) C1 0.0343(18) 0.059(2) 0.0387(18) -0.0022(15) -0.0070(15) -0.0073(15) C2 0.0244(15) 0.0428(17) 0.0269(15) -0.0078(12) 0.0034(12) -0.0036(12) C3 0.0302(16) 0.0354(16) 0.0334(16) -0.0117(12) 0.0038(13) -0.0056(12) C4 0.0291(15) 0.0286(14) 0.0305(15) -0.0099(11) 0.0081(12) 0.0008(11) C5 0.0386(18) 0.0236(14) 0.0490(19) -0.0059(13) 0.0066(15) -0.0012(12) C6 0.0290(15) 0.0188(13) 0.0232(14) 0.0022(10) 0.0066(12) 0.0024(10) C7 0.0255(15) 0.0253(14) 0.0220(14) 0.0038(10) 0.0037(12) 0.0041(10) C8 0.0241(14) 0.0295(14) 0.0202(13) 0.0001(11) 0.0028(11) 0.0016(10) C9 0.0247(14) 0.0192(13) 0.0218(13) 0.0018(10) 0.0076(11) 0.0024(10) C10 0.0226(14) 0.0232(13) 0.0212(14) 0.0003(10) 0.0067(11) 0.0008(10) C11 0.0245(14) 0.0230(13) 0.0230(14) 0.0009(10) 0.0072(12) 0.0049(11) C12 0.0318(17) 0.0314(16) 0.0244(15) 0.0033(11) 0.0017(13) 0.0075(11) C13 0.0384(17) 0.0300(16) 0.0261(14) 0.0078(12) 0.0001(13) 0.0108(12) C14 0.0381(17) 0.0231(14) 0.0328(16) 0.0067(11) 0.0093(13) 0.0081(12) C15 0.0304(15) 0.0208(13) 0.0264(14) 0.0014(11) 0.0066(12) 0.0024(11) C16 0.0264(15) 0.0205(13) 0.0277(14) -0.0008(10) 0.0108(12) -0.0004(10) C17 0.0241(15) 0.0226(13) 0.0274(15) -0.0042(11) 0.0090(12) -0.0017(10) C18 0.0317(13) 0.0244(12) 0.0362(13) -0.0037(10) 0.0112(10) 0.0004(10) C19 0.0240(14) 0.0242(13) 0.0326(15) -0.0017(11) 0.0098(12) -0.0004(10) C20 0.0325(17) 0.0290(15) 0.0490(18) 0.0114(13) -0.0001(14) 0.0009(12) C21 0.0301(17) 0.0474(19) 0.0465(19) 0.0073(15) -0.0082(15) -0.0040(14) C22 0.053(2) 0.0262(15) 0.0392(18) 0.0017(13) -0.0046(16) -0.0045(13) C23 0.0448(19) 0.0255(15) 0.0342(16) -0.0004(12) -0.0064(14) -0.0004(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.924(2) . ? Cu1 O2 1.9252(18) . ? Cu1 N2 2.012(2) . ? Cu1 N1 2.020(2) . ? Cu1 O3 2.214(2) . ? N1 C6 1.334(3) . ? N1 C9 1.366(3) . ? N2 C12 1.334(3) . ? N2 C11 1.359(3) . ? N3 C18 1.300(4) . ? N3 C16 1.385(3) . ? O6 C17 1.361(3) . ? O6 C18 1.368(3) . ? N4 C21 1.328(4) . ? N4 C22 1.343(4) . ? N5 O3 1.215(3) . ? N5 O4 1.260(3) . ? N5 O5 1.269(3) . ? O1 C2 1.281(3) . ? O2 C4 1.277(3) . ? C1 C2 1.509(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.398(4) . ? C3 C4 1.398(4) . ? C3 H3 0.9500 . ? C4 C5 1.511(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.400(4) . ? C6 H6 0.9500 . ? C7 C8 1.376(4) . ? C7 H7 0.9500 . ? C8 C10 1.411(4) . ? C8 H8 0.9500 . ? C9 C10 1.406(4) . ? C9 C11 1.451(4) . ? C10 C17 1.435(3) . ? C11 C15 1.402(4) . ? C12 C13 1.407(4) . ? C12 H12 0.9500 . ? C13 C14 1.363(4) . ? C13 H13 0.9500 . ? C14 C15 1.418(4) . ? C14 H14 0.9500 . ? C15 C16 1.430(4) . ? C16 C17 1.375(4) . ? C18 C19 1.463(4) . ? C19 C20 1.379(4) . ? C19 C23 1.398(4) . ? C20 C21 1.396(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.383(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 O2 94.19(8) . . ? O1 Cu1 N2 90.31(8) . . ? O2 Cu1 N2 166.03(8) . . ? O1 Cu1 N1 167.73(9) . . ? O2 Cu1 N1 91.19(8) . . ? N2 Cu1 N1 82.01(8) . . ? O1 Cu1 O3 90.80(8) . . ? O2 Cu1 O3 94.61(8) . . ? N2 Cu1 O3 98.55(8) . . ? N1 Cu1 O3 99.76(8) . . ? C6 N1 C9 118.7(2) . . ? C6 N1 Cu1 128.52(18) . . ? C9 N1 Cu1 112.65(16) . . ? C12 N2 C11 119.1(2) . . ? C12 N2 Cu1 127.81(19) . . ? C11 N2 Cu1 112.91(16) . . ? C18 N3 C16 104.5(2) . . ? C17 O6 C18 104.1(2) . . ? C21 N4 C22 116.2(3) . . ? O3 N5 O4 122.6(2) . . ? O3 N5 O5 120.7(2) . . ? O4 N5 O5 116.6(2) . . ? C2 O1 Cu1 125.27(18) . . ? C4 O2 Cu1 124.70(18) . . ? N5 O3 Cu1 123.88(16) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 124.5(3) . . ? O1 C2 C1 115.3(3) . . ? C3 C2 C1 120.1(3) . . ? C2 C3 C4 125.1(3) . . ? C2 C3 H3 117.5 . . ? C4 C3 H3 117.5 . . ? O2 C4 C3 125.5(3) . . ? O2 C4 C5 114.7(3) . . ? C3 C4 C5 119.9(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 122.0(2) . . ? N1 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C10 118.1(2) . . ? C7 C8 H8 121.0 . . ? C10 C8 H8 121.0 . . ? N1 C9 C10 122.0(2) . . ? N1 C9 C11 115.8(2) . . ? C10 C9 C11 122.2(2) . . ? C9 C10 C8 118.6(2) . . ? C9 C10 C17 114.3(2) . . ? C8 C10 C17 127.0(2) . . ? N2 C11 C15 122.1(2) . . ? N2 C11 C9 116.2(2) . . ? C15 C11 C9 121.6(2) . . ? N2 C12 C13 122.0(3) . . ? N2 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 119.5(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C11 C15 C14 117.7(2) . . ? C11 C15 C16 115.8(2) . . ? C14 C15 C16 126.5(2) . . ? C17 C16 N3 108.7(2) . . ? C17 C16 C15 122.1(2) . . ? N3 C16 C15 129.2(2) . . ? O6 C17 C16 108.1(2) . . ? O6 C17 C10 128.0(2) . . ? C16 C17 C10 123.9(2) . . ? N3 C18 O6 114.5(2) . . ? N3 C18 C19 126.8(2) . . ? O6 C18 C19 118.7(2) . . ? C20 C19 C23 118.0(3) . . ? C20 C19 C18 122.3(2) . . ? C23 C19 C18 119.7(3) . . ? C19 C20 C21 118.5(3) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? N4 C21 C20 124.5(3) . . ? N4 C21 H21 117.7 . . ? C20 C21 H21 117.7 . . ? N4 C22 C23 124.0(3) . . ? N4 C22 H22 118.0 . . ? C23 C22 H22 118.0 . . ? C22 C23 C19 118.8(3) . . ? C22 C23 H23 120.6 . . ? C19 C23 H23 120.6 . . ? 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 O1 Cu1 N1 C6 -127.6(4) . . . . ? O2 Cu1 N1 C6 -11.5(2) . . . . ? N2 Cu1 N1 C6 -179.3(2) . . . . ? O3 Cu1 N1 C6 83.3(2) . . . . ? O1 Cu1 N1 C9 57.4(5) . . . . ? O2 Cu1 N1 C9 173.45(18) . . . . ? N2 Cu1 N1 C9 5.69(18) . . . . ? O3 Cu1 N1 C9 -91.67(18) . . . . ? O1 Cu1 N2 C12 9.2(2) . . . . ? O2 Cu1 N2 C12 118.2(4) . . . . ? N1 Cu1 N2 C12 179.7(2) . . . . ? O3 Cu1 N2 C12 -81.6(2) . . . . ? O1 Cu1 N2 C11 -176.15(19) . . . . ? O2 Cu1 N2 C11 -67.2(4) . . . . ? N1 Cu1 N2 C11 -5.74(18) . . . . ? O3 Cu1 N2 C11 93.00(19) . . . . ? O2 Cu1 O1 C2 8.9(2) . . . . ? N2 Cu1 O1 C2 175.7(2) . . . . ? N1 Cu1 O1 C2 124.7(4) . . . . ? O3 Cu1 O1 C2 -85.7(2) . . . . ? O1 Cu1 O2 C4 -6.7(2) . . . . ? N2 Cu1 O2 C4 -115.2(4) . . . . ? N1 Cu1 O2 C4 -175.7(2) . . . . ? O3 Cu1 O2 C4 84.4(2) . . . . ? O4 N5 O3 Cu1 -3.1(3) . . . . ? O5 N5 O3 Cu1 172.31(17) . . . . ? O1 Cu1 O3 N5 -124.30(19) . . . . ? O2 Cu1 O3 N5 141.43(18) . . . . ? N2 Cu1 O3 N5 -33.87(19) . . . . ? N1 Cu1 O3 N5 49.43(19) . . . . ? Cu1 O1 C2 C3 -5.7(4) . . . . ? Cu1 O1 C2 C1 177.1(2) . . . . ? O1 C2 C3 C4 -2.9(5) . . . . ? C1 C2 C3 C4 174.2(3) . . . . ? Cu1 O2 C4 C3 1.2(4) . . . . ? Cu1 O2 C4 C5 179.53(18) . . . . ? C2 C3 C4 O2 5.4(5) . . . . ? C2 C3 C4 C5 -172.9(3) . . . . ? C9 N1 C6 C7 -1.3(4) . . . . ? Cu1 N1 C6 C7 -176.08(19) . . . . ? N1 C6 C7 C8 1.4(4) . . . . ? C6 C7 C8 C10 -0.2(4) . . . . ? C6 N1 C9 C10 0.1(4) . . . . ? Cu1 N1 C9 C10 175.61(19) . . . . ? C6 N1 C9 C11 179.7(2) . . . . ? Cu1 N1 C9 C11 -4.7(3) . . . . ? N1 C9 C10 C8 1.1(4) . . . . ? C11 C9 C10 C8 -178.5(2) . . . . ? N1 C9 C10 C17 -177.6(2) . . . . ? C11 C9 C10 C17 2.8(4) . . . . ? C7 C8 C10 C9 -1.0(4) . . . . ? C7 C8 C10 C17 177.5(3) . . . . ? C12 N2 C11 C15 1.2(4) . . . . ? Cu1 N2 C11 C15 -173.92(19) . . . . ? C12 N2 C11 C9 180.0(2) . . . . ? Cu1 N2 C11 C9 4.9(3) . . . . ? N1 C9 C11 N2 -0.1(3) . . . . ? C10 C9 C11 N2 179.6(2) . . . . ? N1 C9 C11 C15 178.7(2) . . . . ? C10 C9 C11 C15 -1.6(4) . . . . ? C11 N2 C12 C13 1.0(4) . . . . ? Cu1 N2 C12 C13 175.3(2) . . . . ? N2 C12 C13 C14 -1.6(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? N2 C11 C15 C14 -2.7(4) . . . . ? C9 C11 C15 C14 178.6(2) . . . . ? N2 C11 C15 C16 177.6(2) . . . . ? C9 C11 C15 C16 -1.1(4) . . . . ? C13 C14 C15 C11 2.0(4) . . . . ? C13 C14 C15 C16 -178.3(3) . . . . ? C18 N3 C16 C17 0.3(3) . . . . ? C18 N3 C16 C15 179.7(3) . . . . ? C11 C15 C16 C17 2.5(4) . . . . ? C14 C15 C16 C17 -177.2(3) . . . . ? C11 C15 C16 N3 -176.8(3) . . . . ? C14 C15 C16 N3 3.5(5) . . . . ? C18 O6 C17 C16 0.8(3) . . . . ? C18 O6 C17 C10 -178.0(3) . . . . ? N3 C16 C17 O6 -0.7(3) . . . . ? C15 C16 C17 O6 179.8(2) . . . . ? N3 C16 C17 C10 178.2(3) . . . . ? C15 C16 C17 C10 -1.3(4) . . . . ? C9 C10 C17 O6 177.3(3) . . . . ? C8 C10 C17 O6 -1.3(5) . . . . ? C9 C10 C17 C16 -1.4(4) . . . . ? C8 C10 C17 C16 -179.9(3) . . . . ? C16 N3 C18 O6 0.2(3) . . . . ? C16 N3 C18 C19 178.7(3) . . . . ? C17 O6 C18 N3 -0.7(3) . . . . ? C17 O6 C18 C19 -179.3(2) . . . . ? N3 C18 C19 C20 178.4(3) . . . . ? O6 C18 C19 C20 -3.1(4) . . . . ? N3 C18 C19 C23 0.4(4) . . . . ? O6 C18 C19 C23 178.9(3) . . . . ? C23 C19 C20 C21 -1.0(5) . . . . ? C18 C19 C20 C21 -179.1(3) . . . . ? C22 N4 C21 C20 0.1(5) . . . . ? C19 C20 C21 N4 0.6(5) . . . . ? C21 N4 C22 C23 -0.3(5) . . . . ? N4 C22 C23 C19 -0.2(5) . . . . ? C20 C19 C23 C22 0.8(4) . . . . ? C18 C19 C23 C22 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.85 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.445 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 930714' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CuacacCl-R3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C24 H21 Cl Cu N5 O7, N O3, H2O ' _chemical_formula_sum 'C24 H23 Cl Cu N6 O11' _chemical_formula_weight 670.47 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.495(2) _cell_length_b 9.358(3) _cell_length_c 17.422(5) _cell_angle_alpha 91.295(6) _cell_angle_beta 96.015(6) _cell_angle_gamma 102.204(6) _cell_volume 1344.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1779 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.36 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 686 _exptl_absorpt_coefficient_mu 0.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8427 _exptl_absorpt_correction_T_max 0.9254 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7313 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_unetI/netI 0.0954 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5014 _reflns_number_gt 3917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The restaints were listed here: exyz O4 N3' exyz N3 O4' eadp O4 N3' eadp N3 O4' ISOR 0.01 N3 O4 ; _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^)+(0.0800P)^2^+2.0000P] 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_number_reflns 5014 _refine_ls_number_parameters 396 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1742 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.040 _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 0.43057(8) 0.65533(8) 0.19543(4) 0.0249(2) Uani 1 1 d . . . Cl1 Cl 0.1967(2) 0.8998(2) -0.02379(11) 0.0599(6) Uani 1 1 d . . . O1 O 0.2519(5) 0.7499(5) 0.1817(2) 0.0336(10) Uani 1 1 d . . . O2 O 0.4887(5) 0.6934(5) 0.0939(2) 0.0340(10) Uani 1 1 d . . . O3 O 0.5977(5) 0.8705(4) 0.2542(2) 0.0348(10) Uani 1 1 d . . . H3 H 0.6643 0.8299 0.2796 0.052 Uiso 1 1 calc R . . O4 O 0.5386(4) 0.2472(4) 0.4833(2) 0.0248(11) Uani 0.89(5) 1 d PU A 1 N3' N 0.5386(4) 0.2472(4) 0.4833(2) 0.0248(11) Uani 0.11(5) 1 d P A 2 O5 O 0.9241(6) 0.7792(7) 0.3248(3) 0.0681(17) Uani 1 1 d . . . O6 O 0.7246(6) 0.7698(7) 0.3919(3) 0.0737(19) Uani 1 1 d . . . O7 O 0.9350(5) 0.6998(5) 0.4389(3) 0.0480(12) Uani 1 1 d . . . O8 O 0.2299(6) 0.3790(5) 0.1446(3) 0.0468(12) Uani 1 1 d . . . O9 O 0.3483(5) 0.2132(5) 0.1941(3) 0.0451(12) Uani 1 1 d . . . O10 O 0.1231(5) 0.2424(5) 0.2316(3) 0.0413(11) Uani 1 1 d . . . N1 N 0.3587(5) 0.5708(5) 0.2943(3) 0.0226(10) Uani 1 1 d . A . N2 N 0.6069(5) 0.5437(5) 0.2194(3) 0.0227(10) Uani 1 1 d . . . N3 N 0.7499(5) 0.2183(5) 0.4211(3) 0.0233(13) Uani 0.89(5) 1 d PU A 1 O4' O 0.7499(5) 0.2183(5) 0.4211(3) 0.0233(13) Uani 0.11(5) 1 d P A 2 N4 N 0.7827(5) -0.0729(5) 0.6608(3) 0.0271(11) Uani 1 1 d . . . H4 H 0.8117 -0.1232 0.6999 0.033 Uiso 1 1 calc R . . N5 N 0.8624(6) 0.7502(5) 0.3849(3) 0.0328(12) Uani 1 1 d . . . N6 N 0.2353(6) 0.2774(5) 0.1885(3) 0.0310(11) Uani 1 1 d . . . O1W O 0.0000 0.5000 0.0000 0.136(5) Uani 1 2 d S B 1 O2W O -0.1367(16) 0.5560(15) 0.0140(7) 0.074(4) Uani 0.50 1 d P C 2 C1 C 0.2063(7) 0.8104(6) 0.1212(4) 0.0328(14) Uani 1 1 d . . . C2 C 0.2823(7) 0.8166(7) 0.0547(4) 0.0349(15) Uani 1 1 d . . . C3 C 0.4163(8) 0.7563(7) 0.0412(3) 0.0355(15) Uani 1 1 d . . . C4 C 0.0599(7) 0.8749(7) 0.1272(4) 0.0412(16) Uani 1 1 d . . . H4A H 0.0237 0.8586 0.1785 0.062 Uiso 1 1 calc R . . H4B H -0.0273 0.8279 0.0876 0.062 Uiso 1 1 calc R . . H4C H 0.0880 0.9803 0.1194 0.062 Uiso 1 1 calc R . . C5 C 0.4833(9) 0.7624(9) -0.0340(4) 0.0521(19) Uani 1 1 d . . . H5A H 0.5757 0.7146 -0.0308 0.078 Uiso 1 1 calc R . . H5B H 0.5191 0.8648 -0.0467 0.078 Uiso 1 1 calc R . . H5C H 0.3995 0.7120 -0.0742 0.078 Uiso 1 1 calc R . . C6 C 0.2301(6) 0.5847(6) 0.3283(3) 0.0241(12) Uani 1 1 d . . . H6A H 0.1606 0.6433 0.3058 0.029 Uiso 1 1 calc R . . C7 C 0.1943(7) 0.5155(6) 0.3961(3) 0.0291(13) Uani 1 1 d . . . H7A H 0.1003 0.5267 0.4187 0.035 Uiso 1 1 calc R . . C8 C 0.2931(6) 0.4312(6) 0.4309(3) 0.0243(12) Uani 1 1 d . . . H8A H 0.2701 0.3850 0.4776 0.029 Uiso 1 1 calc R . . C9 C 0.4285(6) 0.4159(6) 0.3949(3) 0.0215(11) Uani 1 1 d . A . C10 C 0.5410(6) 0.3307(6) 0.4192(3) 0.0234(12) Uani 1 1 d . . . C11 C 0.6703(6) 0.3122(6) 0.3815(3) 0.0232(12) Uani 1 1 d . A . C12 C 0.7025(6) 0.3852(6) 0.3120(3) 0.0209(11) Uani 1 1 d . . . C13 C 0.8301(6) 0.3782(6) 0.2681(3) 0.0265(12) Uani 1 1 d . A . H13A H 0.9078 0.3224 0.2844 0.032 Uiso 1 1 calc R . . C14 C 0.8415(7) 0.4521(6) 0.2019(3) 0.0291(13) Uani 1 1 d . . . H14A H 0.9270 0.4474 0.1716 0.035 Uiso 1 1 calc R A . C15 C 0.7282(6) 0.5345(6) 0.1786(3) 0.0272(13) Uani 1 1 d . A . H15A H 0.7378 0.5856 0.1323 0.033 Uiso 1 1 calc R . . C16 C 0.5928(6) 0.4720(6) 0.2855(3) 0.0212(11) Uani 1 1 d . A . C17 C 0.4575(6) 0.4859(5) 0.3263(3) 0.0200(11) Uani 1 1 d . . . C18 C 0.6683(7) 0.1834(6) 0.4797(3) 0.0252(12) Uani 1 1 d . . . C19 C 0.7020(6) 0.0898(5) 0.5428(3) 0.0204(11) Uani 1 1 d . A . C20 C 0.6247(7) 0.0849(6) 0.6088(3) 0.0274(13) Uani 1 1 d . . . H20A H 0.5427 0.1387 0.6132 0.033 Uiso 1 1 calc R A . C21 C 0.6673(6) 0.0017(6) 0.6680(3) 0.0266(12) Uani 1 1 d . A . H21A H 0.6150 -0.0027 0.7138 0.032 Uiso 1 1 calc R . . C22 C 0.8555(6) -0.0746(6) 0.5976(3) 0.0262(13) Uani 1 1 d . A . H22A H 0.9347 -0.1321 0.5948 0.031 Uiso 1 1 calc R . . C23 C 0.8182(6) 0.0054(6) 0.5360(3) 0.0274(13) Uani 1 1 d . . . H23A H 0.8695 0.0037 0.4901 0.033 Uiso 1 1 calc R A . C24 C 0.6813(9) 0.9784(7) 0.2093(5) 0.053(2) Uani 1 1 d . . . H24A H 0.7625 1.0488 0.2430 0.080 Uiso 1 1 calc R . . H24B H 0.6042 1.0294 0.1819 0.080 Uiso 1 1 calc R . . H24C H 0.7351 0.9320 0.1717 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0263(4) 0.0278(4) 0.0247(4) 0.0102(3) 0.0043(3) 0.0131(3) Cl1 0.0592(12) 0.0729(14) 0.0509(11) 0.0365(10) -0.0039(9) 0.0228(10) O1 0.033(2) 0.044(3) 0.032(2) 0.012(2) 0.0057(18) 0.025(2) O2 0.037(2) 0.041(3) 0.029(2) 0.0176(19) 0.0042(19) 0.0161(19) O3 0.032(2) 0.034(2) 0.039(2) 0.009(2) 0.0020(19) 0.0086(18) O4 0.025(2) 0.023(2) 0.030(2) 0.0074(17) 0.0050(17) 0.0107(16) N3' 0.025(2) 0.023(2) 0.030(2) 0.0074(17) 0.0050(17) 0.0107(16) O5 0.058(3) 0.093(4) 0.045(3) 0.022(3) 0.007(3) -0.006(3) O6 0.048(3) 0.135(5) 0.052(3) -0.022(3) -0.010(3) 0.062(3) O7 0.041(3) 0.056(3) 0.056(3) 0.022(3) 0.013(2) 0.023(2) O8 0.066(3) 0.039(3) 0.036(3) 0.023(2) 0.008(2) 0.010(2) O9 0.040(3) 0.054(3) 0.050(3) 0.016(2) 0.017(2) 0.022(2) O10 0.040(2) 0.049(3) 0.046(3) 0.024(2) 0.023(2) 0.025(2) N1 0.023(2) 0.020(2) 0.025(2) 0.0009(19) 0.0008(19) 0.0070(19) N2 0.021(2) 0.025(2) 0.024(2) 0.006(2) 0.0050(19) 0.0076(19) N3 0.022(2) 0.020(2) 0.029(3) 0.0061(19) 0.0009(19) 0.0060(18) O4' 0.022(2) 0.020(2) 0.029(3) 0.0061(19) 0.0009(19) 0.0060(18) N4 0.030(3) 0.024(3) 0.032(3) 0.017(2) 0.008(2) 0.010(2) N5 0.029(3) 0.030(3) 0.038(3) -0.001(2) -0.001(2) 0.006(2) N6 0.040(3) 0.023(3) 0.029(3) 0.004(2) 0.002(2) 0.007(2) O1W 0.165(13) 0.110(10) 0.111(10) 0.002(8) -0.006(10) -0.008(10) O2W 0.086(9) 0.097(10) 0.051(7) 0.005(7) 0.011(7) 0.042(8) C1 0.028(3) 0.030(3) 0.037(4) 0.006(3) -0.007(3) 0.003(3) C2 0.035(3) 0.036(4) 0.033(3) 0.015(3) -0.004(3) 0.010(3) C3 0.042(4) 0.035(4) 0.024(3) 0.008(3) 0.002(3) -0.002(3) C4 0.037(4) 0.036(4) 0.053(4) 0.013(3) -0.005(3) 0.017(3) C5 0.058(5) 0.067(5) 0.029(4) 0.013(4) 0.005(3) 0.007(4) C6 0.022(3) 0.019(3) 0.031(3) 0.002(2) 0.004(2) 0.005(2) C7 0.021(3) 0.030(3) 0.037(3) -0.007(3) 0.007(2) 0.005(2) C8 0.022(3) 0.025(3) 0.025(3) 0.003(2) 0.005(2) 0.003(2) C9 0.024(3) 0.019(3) 0.023(3) 0.005(2) 0.004(2) 0.007(2) C10 0.025(3) 0.028(3) 0.019(3) 0.009(2) 0.002(2) 0.009(2) C11 0.023(3) 0.021(3) 0.026(3) 0.006(2) 0.002(2) 0.005(2) C12 0.019(3) 0.017(3) 0.025(3) 0.002(2) 0.002(2) 0.003(2) C13 0.023(3) 0.027(3) 0.032(3) 0.005(3) 0.002(2) 0.010(2) C14 0.021(3) 0.036(3) 0.033(3) 0.004(3) 0.011(2) 0.010(2) C15 0.023(3) 0.031(3) 0.028(3) 0.005(3) 0.005(2) 0.005(2) C16 0.020(3) 0.022(3) 0.021(3) 0.003(2) 0.001(2) 0.002(2) C17 0.016(2) 0.019(3) 0.026(3) 0.002(2) 0.002(2) 0.005(2) C18 0.027(3) 0.020(3) 0.030(3) 0.005(2) 0.001(2) 0.008(2) C19 0.020(3) 0.017(3) 0.024(3) 0.001(2) 0.002(2) 0.003(2) C20 0.024(3) 0.028(3) 0.035(3) 0.009(3) 0.009(2) 0.013(2) C21 0.027(3) 0.029(3) 0.026(3) 0.002(2) 0.010(2) 0.007(2) C22 0.022(3) 0.023(3) 0.038(3) 0.012(3) 0.011(2) 0.009(2) C23 0.020(3) 0.031(3) 0.033(3) 0.012(3) 0.011(2) 0.004(2) C24 0.058(5) 0.032(4) 0.070(5) 0.010(4) 0.011(4) 0.007(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 O2 1.907(4) . ? Cu1 O1 1.909(4) . ? Cu1 N1 2.011(5) . ? Cu1 N2 2.015(4) . ? Cu1 O3 2.348(4) . ? Cl1 C2 1.756(6) . ? O1 C1 1.272(7) . ? O2 C3 1.275(7) . ? O3 C24 1.409(8) . ? O3 H3 0.8400 . ? O4 C18 1.366(6) . ? O4 C10 1.377(6) . ? O5 N5 1.229(7) . ? O6 N5 1.241(6) . ? O7 N5 1.228(6) . ? O8 N6 1.238(6) . ? O9 N6 1.233(6) . ? O10 N6 1.269(6) . ? N1 C6 1.324(7) . ? N1 C17 1.360(6) . ? N2 C15 1.328(7) . ? N2 C16 1.349(7) . ? N3 C18 1.302(7) . ? N3 C11 1.375(6) . ? N4 C22 1.320(7) . ? N4 C21 1.333(7) . ? N4 H4 0.8800 . ? C1 C2 1.380(9) . ? C1 C4 1.505(8) . ? C2 C3 1.411(9) . ? C3 C5 1.480(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.390(8) . ? C6 H6A 0.9500 . ? C7 C8 1.374(8) . ? C7 H7A 0.9500 . ? C8 C9 1.397(7) . ? C8 H8A 0.9500 . ? C9 C17 1.396(7) . ? C9 C10 1.408(7) . ? C10 C11 1.376(7) . ? C11 C12 1.425(7) . ? C12 C13 1.403(7) . ? C12 C16 1.411(7) . ? C13 C14 1.359(8) . ? C13 H13A 0.9500 . ? C14 C15 1.390(8) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.440(7) . ? C18 C19 1.463(7) . ? C19 C20 1.381(7) . ? C19 C23 1.401(7) . ? C20 C21 1.370(8) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.371(8) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O1 93.47(17) . . ? O2 Cu1 N1 167.90(18) . . ? O1 Cu1 N1 91.56(17) . . ? O2 Cu1 N2 92.47(17) . . ? O1 Cu1 N2 173.63(18) . . ? N1 Cu1 N2 82.17(17) . . ? O2 Cu1 O3 95.48(17) . . ? O1 Cu1 O3 90.64(17) . . ? N1 Cu1 O3 95.45(16) . . ? N2 Cu1 O3 91.09(16) . . ? C1 O1 Cu1 126.4(4) . . ? C3 O2 Cu1 127.5(4) . . ? C24 O3 Cu1 120.6(4) . . ? C24 O3 H3 109.5 . . ? Cu1 O3 H3 96.6 . . ? C18 O4 C10 103.5(4) . . ? C6 N1 C17 119.1(5) . . ? C6 N1 Cu1 128.6(4) . . ? C17 N1 Cu1 112.3(3) . . ? C15 N2 C16 119.5(5) . . ? C15 N2 Cu1 127.8(4) . . ? C16 N2 Cu1 112.6(3) . . ? C18 N3 C11 104.4(4) . . ? C22 N4 C21 122.9(5) . . ? C22 N4 H4 118.6 . . ? C21 N4 H4 118.6 . . ? O7 N5 O5 120.8(5) . . ? O7 N5 O6 118.6(6) . . ? O5 N5 O6 120.6(6) . . ? O9 N6 O8 122.7(5) . . ? O9 N6 O10 118.9(5) . . ? O8 N6 O10 118.4(5) . . ? O1 C1 C2 123.7(5) . . ? O1 C1 C4 114.4(6) . . ? C2 C1 C4 121.9(5) . . ? C1 C2 C3 127.1(5) . . ? C1 C2 Cl1 116.7(5) . . ? C3 C2 Cl1 116.1(5) . . ? O2 C3 C2 121.7(6) . . ? O2 C3 C5 115.5(6) . . ? C2 C3 C5 122.8(6) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 121.7(5) . . ? N1 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C8 C7 C6 120.9(5) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C9 117.6(5) . . ? C7 C8 H8A 121.2 . . ? C9 C8 H8A 121.2 . . ? C17 C9 C8 119.2(5) . . ? C17 C9 C10 114.1(5) . . ? C8 C9 C10 126.6(5) . . ? C11 C10 O4 107.8(4) . . ? C11 C10 C9 125.9(5) . . ? O4 C10 C9 126.3(5) . . ? N3 C11 C10 109.3(5) . . ? N3 C11 C12 130.3(5) . . ? C10 C11 C12 120.4(5) . . ? C13 C12 C16 117.6(5) . . ? C13 C12 C11 126.7(5) . . ? C16 C12 C11 115.7(5) . . ? C14 C13 C12 119.3(5) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C13 C14 C15 120.1(5) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? N2 C15 C14 121.7(5) . . ? N2 C15 H15A 119.1 . . ? C14 C15 H15A 119.1 . . ? N2 C16 C12 121.6(5) . . ? N2 C16 C17 116.4(5) . . ? C12 C16 C17 121.9(5) . . ? N1 C17 C9 121.5(5) . . ? N1 C17 C16 116.5(5) . . ? C9 C17 C16 122.0(5) . . ? N3 C18 O4 115.1(5) . . ? N3 C18 C19 128.2(5) . . ? O4 C18 C19 116.7(5) . . ? C20 C19 C23 119.6(5) . . ? C20 C19 C18 121.7(5) . . ? C23 C19 C18 118.6(5) . . ? C21 C20 C19 119.4(5) . . ? C21 C20 H20A 120.3 . . ? C19 C20 H20A 120.3 . . ? N4 C21 C20 119.4(5) . . ? N4 C21 H21A 120.3 . . ? C20 C21 H21A 120.3 . . ? N4 C22 C23 120.8(5) . . ? N4 C22 H22A 119.6 . . ? C23 C22 H22A 119.6 . . ? C22 C23 C19 117.8(5) . . ? C22 C23 H23A 121.1 . . ? C19 C23 H23A 121.1 . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 O2 Cu1 O1 C1 0.2(5) . . . . ? N1 Cu1 O1 C1 -168.8(5) . . . . ? N2 Cu1 O1 C1 -158.5(15) . . . . ? O3 Cu1 O1 C1 95.8(5) . . . . ? O1 Cu1 O2 C3 -2.4(5) . . . . ? N1 Cu1 O2 C3 112.0(9) . . . . ? N2 Cu1 O2 C3 175.3(5) . . . . ? O3 Cu1 O2 C3 -93.4(5) . . . . ? O2 Cu1 O3 C24 6.6(5) . . . . ? O1 Cu1 O3 C24 -86.9(5) . . . . ? N1 Cu1 O3 C24 -178.6(4) . . . . ? N2 Cu1 O3 C24 99.2(4) . . . . ? O2 Cu1 N1 C6 -113.6(8) . . . . ? O1 Cu1 N1 C6 1.0(5) . . . . ? N2 Cu1 N1 C6 -177.9(5) . . . . ? O3 Cu1 N1 C6 91.7(5) . . . . ? O2 Cu1 N1 C17 64.2(9) . . . . ? O1 Cu1 N1 C17 178.8(4) . . . . ? N2 Cu1 N1 C17 -0.1(4) . . . . ? O3 Cu1 N1 C17 -90.4(4) . . . . ? O2 Cu1 N2 C15 10.5(5) . . . . ? O1 Cu1 N2 C15 169.3(15) . . . . ? N1 Cu1 N2 C15 179.7(5) . . . . ? O3 Cu1 N2 C15 -85.0(5) . . . . ? O2 Cu1 N2 C16 -169.3(4) . . . . ? O1 Cu1 N2 C16 -10.5(19) . . . . ? N1 Cu1 N2 C16 -0.2(4) . . . . ? O3 Cu1 N2 C16 95.1(4) . . . . ? Cu1 O1 C1 C2 0.0(9) . . . . ? Cu1 O1 C1 C4 179.4(4) . . . . ? O1 C1 C2 C3 1.7(11) . . . . ? C4 C1 C2 C3 -177.7(6) . . . . ? O1 C1 C2 Cl1 177.9(5) . . . . ? C4 C1 C2 Cl1 -1.5(8) . . . . ? Cu1 O2 C3 C2 4.3(9) . . . . ? Cu1 O2 C3 C5 -176.3(4) . . . . ? C1 C2 C3 O2 -3.9(11) . . . . ? Cl1 C2 C3 O2 179.8(5) . . . . ? C1 C2 C3 C5 176.7(7) . . . . ? Cl1 C2 C3 C5 0.4(9) . . . . ? C17 N1 C6 C7 0.5(8) . . . . ? Cu1 N1 C6 C7 178.2(4) . . . . ? N1 C6 C7 C8 0.8(8) . . . . ? C6 C7 C8 C9 -1.0(8) . . . . ? C7 C8 C9 C17 0.1(8) . . . . ? C7 C8 C9 C10 -177.5(5) . . . . ? C18 O4 C10 C11 0.0(6) . . . . ? C18 O4 C10 C9 178.0(5) . . . . ? C17 C9 C10 C11 -0.3(8) . . . . ? C8 C9 C10 C11 177.3(6) . . . . ? C17 C9 C10 O4 -178.1(5) . . . . ? C8 C9 C10 O4 -0.4(9) . . . . ? C18 N3 C11 C10 0.3(6) . . . . ? C18 N3 C11 C12 -179.3(6) . . . . ? O4 C10 C11 N3 -0.1(6) . . . . ? C9 C10 C11 N3 -178.2(5) . . . . ? O4 C10 C11 C12 179.5(5) . . . . ? C9 C10 C11 C12 1.4(9) . . . . ? N3 C11 C12 C13 -1.3(10) . . . . ? C10 C11 C12 C13 179.2(6) . . . . ? N3 C11 C12 C16 178.3(5) . . . . ? C10 C11 C12 C16 -1.2(8) . . . . ? C16 C12 C13 C14 -1.1(8) . . . . ? C11 C12 C13 C14 178.4(5) . . . . ? C12 C13 C14 C15 0.5(9) . . . . ? C16 N2 C15 C14 0.3(8) . . . . ? Cu1 N2 C15 C14 -179.6(4) . . . . ? C13 C14 C15 N2 -0.1(9) . . . . ? C15 N2 C16 C12 -1.0(8) . . . . ? Cu1 N2 C16 C12 178.9(4) . . . . ? C15 N2 C16 C17 -179.4(5) . . . . ? Cu1 N2 C16 C17 0.4(6) . . . . ? C13 C12 C16 N2 1.4(8) . . . . ? C11 C12 C16 N2 -178.2(5) . . . . ? C13 C12 C16 C17 179.8(5) . . . . ? C11 C12 C16 C17 0.2(7) . . . . ? C6 N1 C17 C9 -1.5(8) . . . . ? Cu1 N1 C17 C9 -179.6(4) . . . . ? C6 N1 C17 C16 178.4(5) . . . . ? Cu1 N1 C17 C16 0.3(6) . . . . ? C8 C9 C17 N1 1.2(8) . . . . ? C10 C9 C17 N1 179.1(5) . . . . ? C8 C9 C17 C16 -178.6(5) . . . . ? C10 C9 C17 C16 -0.8(7) . . . . ? N2 C16 C17 N1 -0.5(7) . . . . ? C12 C16 C17 N1 -179.0(5) . . . . ? N2 C16 C17 C9 179.4(5) . . . . ? C12 C16 C17 C9 0.9(8) . . . . ? C11 N3 C18 O4 -0.3(6) . . . . ? C11 N3 C18 C19 -177.7(5) . . . . ? C10 O4 C18 N3 0.2(6) . . . . ? C10 O4 C18 C19 178.0(4) . . . . ? N3 C18 C19 C20 167.0(6) . . . . ? O4 C18 C19 C20 -10.4(8) . . . . ? N3 C18 C19 C23 -11.8(9) . . . . ? O4 C18 C19 C23 170.8(5) . . . . ? C23 C19 C20 C21 2.5(8) . . . . ? C18 C19 C20 C21 -176.3(5) . . . . ? C22 N4 C21 C20 -2.3(9) . . . . ? C19 C20 C21 N4 0.1(8) . . . . ? C21 N4 C22 C23 2.0(9) . . . . ? N4 C22 C23 C19 0.7(8) . . . . ? C20 C19 C23 C22 -2.8(8) . . . . ? C18 C19 C23 C22 176.0(5) . . . . ? 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 C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 O3 H3 N5 0.84 2.59 3.408(6) 165.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 O5 0.84 2.41 3.204(7) 157.7 . C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 O3 H3 N5 0.84 2.59 3.408(6) 165.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 O5 0.84 2.41 3.204(7) 157.7 . C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 O3 H3 N5 0.84 2.59 3.408(6) 165.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 O5 0.84 2.41 3.204(7) 157.7 . C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 O3 H3 N5 0.84 2.59 3.408(6) 165.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 O5 0.84 2.41 3.204(7) 157.7 . O3 H3 O5 0.84 2.41 3.204(7) 157.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 N5 0.84 2.59 3.408(6) 165.7 . N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 O3 H3 O5 0.84 2.41 3.204(7) 157.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 N5 0.84 2.59 3.408(6) 165.7 . N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 O3 H3 O5 0.84 2.41 3.204(7) 157.7 . O3 H3 O6 0.84 2.09 2.791(7) 140.7 . O3 H3 N5 0.84 2.59 3.408(6) 165.7 . N4 H4 O9 0.88 2.47 3.079(6) 127.2 2_656 N4 H4 O10 0.88 1.78 2.651(6) 171.5 2_656 N4 H4 N6 0.88 2.46 3.282(7) 154.9 2_656 C6 H6A O1 0.95 2.53 3.018(7) 112.1 . C6 H6A O5 0.95 2.64 3.470(8) 146.6 1_455 C7 H7A O7 0.95 2.40 3.205(7) 142.4 1_455 C15 H15A O2 0.95 2.57 3.046(7) 111.6 . C15 H15A O2W 0.95 2.45 3.194(13) 134.7 1_655 C20 H20A O6 0.95 2.58 3.514(7) 166.3 2_666 C21 H21A O3 0.95 2.50 3.168(7) 127.7 2_666 C21 H21A O9 0.95 2.62 3.164(7) 117.0 2_656 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.825 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.120 _database_code_depnum_ccdc_archive 'CCDC 930715'