# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_1 _database_code_depnum_ccdc_archive 'CCDC 901461' #TrackingRef 'Full Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H68 Cu4 N8 O4' _chemical_formula_weight 883.10 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4470(2) _cell_length_b 11.9090(2) _cell_length_c 18.1380(3) _cell_angle_alpha 108.5190(10) _cell_angle_beta 99.5910(10) _cell_angle_gamma 91.2370(10) _cell_volume 2103.14(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9641 _cell_measurement_theta_min 8.52 _cell_measurement_theta_max 28.30 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 2.037 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7777 _exptl_absorpt_correction_T_max 0.8540 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; This crystal was weakly diffracting and there was no observable data above the 2theta limit recorded. ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26887 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 8.52 _diffrn_reflns_theta_max 28.30 _reflns_number_total 9641 _reflns_number_gt 7286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0406P)^2^+0.9335P] 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 9641 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.57255(3) 0.26080(3) 0.528567(16) 0.02399(8) Uani 1 1 d . . . Cu2 Cu -0.36582(3) 0.23521(2) 0.478750(16) 0.02341(8) Uani 1 1 d . . . Cu3 Cu -0.13355(3) 0.26846(2) 0.031911(17) 0.02524(9) Uani 1 1 d . . . Cu4 Cu 0.06521(3) 0.24074(2) -0.027196(16) 0.02516(9) Uani 1 1 d . . . N1 N -0.63879(19) 0.31274(18) 0.44331(12) 0.0254(4) Uani 1 1 d . . . N2 N -0.45100(19) 0.26829(17) 0.38915(11) 0.0237(4) Uani 1 1 d . . . N3 N -0.4954(2) 0.20842(18) 0.61129(12) 0.0258(4) Uani 1 1 d . . . N4 N -0.29316(19) 0.20607(18) 0.57231(12) 0.0256(4) Uani 1 1 d . . . N5 N -0.2166(2) 0.14125(18) -0.05540(12) 0.0285(4) Uani 1 1 d . . . N6 N -0.0221(2) 0.10146(17) -0.10261(12) 0.0274(4) Uani 1 1 d . . . N7 N -0.0366(2) 0.39099(17) 0.11683(11) 0.0258(4) Uani 1 1 d . . . N8 N 0.1398(2) 0.38139(17) 0.05137(12) 0.0275(4) Uani 1 1 d . . . O1 O -0.62371(16) 0.34192(14) 0.32473(9) 0.0264(3) Uani 1 1 d . . . O2 O -0.31790(17) 0.15344(15) 0.68269(10) 0.0285(4) Uani 1 1 d . . . O3 O -0.20651(18) -0.02713(14) -0.16271(10) 0.0298(4) Uani 1 1 d . . . O4 O 0.14396(17) 0.52762(14) 0.17151(10) 0.0288(4) Uani 1 1 d . . . C1 C -0.5688(2) 0.30725(19) 0.38814(13) 0.0219(4) Uani 1 1 d . . . C2 C -0.5914(3) 0.4662(2) 0.33729(18) 0.0361(6) Uani 1 1 d . . . H2A H -0.6149 0.5147 0.3872 0.054 Uiso 1 1 calc R . . H2B H -0.6398 0.4884 0.2936 0.054 Uiso 1 1 calc R . . H2C H -0.4977 0.4796 0.3396 0.054 Uiso 1 1 calc R . . C3 C -0.7706(2) 0.3540(2) 0.43642(15) 0.0279(5) Uani 1 1 d . . . H3 H -0.7806 0.3990 0.3980 0.033 Uiso 1 1 calc R . . C4 C -0.7887(3) 0.4367(3) 0.51719(19) 0.0460(7) Uani 1 1 d . . . H4A H -0.7800 0.3929 0.5551 0.069 Uiso 1 1 calc R . . H4B H -0.8755 0.4664 0.5126 0.069 Uiso 1 1 calc R . . H4C H -0.7223 0.5038 0.5357 0.069 Uiso 1 1 calc R . . C5 C -0.8710(3) 0.2479(3) 0.4063(2) 0.0462(7) Uani 1 1 d . . . H5A H -0.8608 0.1988 0.3532 0.069 Uiso 1 1 calc R . . H5B H -0.9586 0.2758 0.4043 0.069 Uiso 1 1 calc R . . H5C H -0.8582 0.2006 0.4420 0.069 Uiso 1 1 calc R . . C6 C -0.3943(2) 0.2431(2) 0.31692(14) 0.0271(5) Uani 1 1 d . . . H6 H -0.4114 0.3085 0.2939 0.033 Uiso 1 1 calc R . . C7 C -0.4544(3) 0.1259(3) 0.25604(17) 0.0437(7) Uani 1 1 d . . . H7A H -0.4303 0.0604 0.2761 0.066 Uiso 1 1 calc R . . H7B H -0.4223 0.1147 0.2066 0.066 Uiso 1 1 calc R . . H7C H -0.5495 0.1270 0.2462 0.066 Uiso 1 1 calc R . . C8 C -0.2481(3) 0.2375(3) 0.33806(16) 0.0344(6) Uani 1 1 d . . . H8A H -0.2093 0.3138 0.3763 0.052 Uiso 1 1 calc R . . H8B H -0.2100 0.2210 0.2902 0.052 Uiso 1 1 calc R . . H8C H -0.2306 0.1743 0.3613 0.052 Uiso 1 1 calc R . . C11 C -0.3700(2) 0.1896(2) 0.61956(13) 0.0233(5) Uani 1 1 d . . . C12 C -0.3014(3) 0.0274(2) 0.65877(18) 0.0401(6) Uani 1 1 d . . . H12A H -0.3851 -0.0170 0.6314 0.060 Uiso 1 1 calc R . . H12B H -0.2695 0.0048 0.7056 0.060 Uiso 1 1 calc R . . H12C H -0.2382 0.0090 0.6231 0.060 Uiso 1 1 calc R . . C13 C -0.5757(2) 0.1825(2) 0.66427(15) 0.0294(5) Uani 1 1 d . . . H13 H -0.5240 0.1389 0.6964 0.035 Uiso 1 1 calc R . . C14 C -0.6104(4) 0.2977(3) 0.7198(2) 0.0557(9) Uani 1 1 d . . . H14A H -0.5305 0.3461 0.7506 0.084 Uiso 1 1 calc R . . H14B H -0.6622 0.2802 0.7558 0.084 Uiso 1 1 calc R . . H14C H -0.6611 0.3414 0.6890 0.084 Uiso 1 1 calc R . . C15 C -0.6954(3) 0.1037(3) 0.6149(2) 0.0492(8) Uani 1 1 d . . . H15A H -0.7446 0.1439 0.5811 0.074 Uiso 1 1 calc R . . H15B H -0.7502 0.0875 0.6498 0.074 Uiso 1 1 calc R . . H15C H -0.6689 0.0287 0.5818 0.074 Uiso 1 1 calc R . . C16 C -0.1506(2) 0.2145(2) 0.59753(14) 0.0274(5) Uani 1 1 d . . . H16 H -0.1308 0.1971 0.6485 0.033 Uiso 1 1 calc R . . C17 C -0.0885(3) 0.1259(3) 0.53687(19) 0.0456(7) Uani 1 1 d . . . H17A H -0.1219 0.0452 0.5306 0.068 Uiso 1 1 calc R . . H17B H 0.0061 0.1346 0.5544 0.068 Uiso 1 1 calc R . . H17C H -0.1096 0.1404 0.4861 0.068 Uiso 1 1 calc R . . C18 C -0.0963(3) 0.3405(3) 0.61140(19) 0.0414(7) Uani 1 1 d . . . H18A H -0.1149 0.3587 0.5618 0.062 Uiso 1 1 calc R . . H18B H -0.0019 0.3476 0.6299 0.062 Uiso 1 1 calc R . . H18C H -0.1370 0.3965 0.6514 0.062 Uiso 1 1 calc R . . C21 C -0.1460(2) 0.0751(2) -0.10453(13) 0.0255(5) Uani 1 1 d . . . C22 C -0.2121(3) -0.1269(2) -0.13443(17) 0.0374(6) Uani 1 1 d . . . H22A H -0.1241 -0.1395 -0.1114 0.056 Uiso 1 1 calc R . . H22B H -0.2488 -0.1981 -0.1786 0.056 Uiso 1 1 calc R . . H22C H -0.2672 -0.1109 -0.0940 0.056 Uiso 1 1 calc R . . C23 C -0.3604(2) 0.1209(2) -0.07517(16) 0.0337(6) Uani 1 1 d . . . H23 H -0.3846 0.0360 -0.1084 0.040 Uiso 1 1 calc R . . C24 C -0.4160(3) 0.1994(4) -0.1211(2) 0.0649(10) Uani 1 1 d . . . H24A H -0.3949 0.2829 -0.0884 0.097 Uiso 1 1 calc R . . H24B H -0.5108 0.1829 -0.1356 0.097 Uiso 1 1 calc R . . H24C H -0.3785 0.1837 -0.1691 0.097 Uiso 1 1 calc R . . C25 C -0.4158(3) 0.1456(4) -0.0003(2) 0.0601(10) Uani 1 1 d . . . H25A H -0.3948 0.2293 0.0319 0.090 Uiso 1 1 calc R . . H25B H -0.3781 0.0950 0.0296 0.090 Uiso 1 1 calc R . . H25C H -0.5106 0.1286 -0.0139 0.090 Uiso 1 1 calc R . . C26 C 0.0503(3) 0.0205(2) -0.15768(14) 0.0303(5) Uani 1 1 d . . . H26 H -0.0053 -0.0555 -0.1856 0.036 Uiso 1 1 calc R . . C27 C 0.0793(4) 0.0747(3) -0.2187(2) 0.0549(9) Uani 1 1 d . . . H27A H -0.0026 0.0905 -0.2475 0.082 Uiso 1 1 calc R . . H27B H 0.1253 0.0194 -0.2559 0.082 Uiso 1 1 calc R . . H27C H 0.1338 0.1493 -0.1922 0.082 Uiso 1 1 calc R . . C28 C 0.1731(3) -0.0066(3) -0.11176(19) 0.0500(8) Uani 1 1 d . . . H28A H 0.2267 0.0675 -0.0818 0.075 Uiso 1 1 calc R . . H28B H 0.2221 -0.0592 -0.1485 0.075 Uiso 1 1 calc R . . H28C H 0.1504 -0.0458 -0.0751 0.075 Uiso 1 1 calc R . . C31 C 0.0800(2) 0.4309(2) 0.11101(14) 0.0247(5) Uani 1 1 d . . . C32 C 0.1023(3) 0.6394(2) 0.16551(16) 0.0345(6) Uani 1 1 d . . . H32A H 0.1082 0.6430 0.1130 0.052 Uiso 1 1 calc R . . H32B H 0.1584 0.7046 0.2060 0.052 Uiso 1 1 calc R . . H32C H 0.0119 0.6465 0.1735 0.052 Uiso 1 1 calc R . . C33 C -0.0744(2) 0.4302(2) 0.19571(14) 0.0274(5) Uani 1 1 d . . . H33 H -0.0505 0.5175 0.2208 0.033 Uiso 1 1 calc R . . C34 C -0.0018(3) 0.3657(2) 0.24821(16) 0.0348(6) Uani 1 1 d . . . H34A H -0.0264 0.2802 0.2250 0.052 Uiso 1 1 calc R . . H34B H -0.0245 0.3951 0.3010 0.052 Uiso 1 1 calc R . . H34C H 0.0922 0.3804 0.2524 0.052 Uiso 1 1 calc R . . C35 C -0.2211(3) 0.4072(3) 0.18677(17) 0.0374(6) Uani 1 1 d . . . H35A H -0.2660 0.4514 0.1543 0.056 Uiso 1 1 calc R . . H35B H -0.2457 0.4333 0.2391 0.056 Uiso 1 1 calc R . . H35C H -0.2460 0.3221 0.1612 0.056 Uiso 1 1 calc R . . C36 C 0.2663(3) 0.4374(2) 0.04950(17) 0.0346(6) Uani 1 1 d . . . H36 H 0.2668 0.5253 0.0748 0.041 Uiso 1 1 calc R . . C37 C 0.2829(3) 0.4118(3) -0.0358(2) 0.0512(8) Uani 1 1 d . . . H37A H 0.2842 0.3259 -0.0610 0.077 Uiso 1 1 calc R . . H37B H 0.3650 0.4519 -0.0370 0.077 Uiso 1 1 calc R . . H37C H 0.2102 0.4410 -0.0643 0.077 Uiso 1 1 calc R . . C38 C 0.3769(3) 0.3928(4) 0.0951(2) 0.0588(9) Uani 1 1 d . . . H38A H 0.3642 0.4100 0.1498 0.088 Uiso 1 1 calc R . . H38B H 0.4597 0.4328 0.0947 0.088 Uiso 1 1 calc R . . H38C H 0.3785 0.3069 0.0704 0.088 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 0.01876(15) 0.03204(17) 0.02388(15) 0.01317(12) 0.00292(11) 0.00489(11) Cu2 0.01807(14) 0.03044(16) 0.02145(14) 0.00880(12) 0.00184(11) 0.00453(11) Cu3 0.02147(15) 0.02408(15) 0.02371(15) -0.00016(11) 0.00248(11) -0.00129(11) Cu4 0.02449(16) 0.02243(15) 0.02444(15) 0.00172(11) 0.00509(12) 0.00036(11) N1 0.0191(9) 0.0319(10) 0.0268(10) 0.0125(8) 0.0026(8) 0.0064(8) N2 0.0203(9) 0.0280(10) 0.0224(9) 0.0077(8) 0.0036(7) 0.0024(7) N3 0.0216(10) 0.0310(10) 0.0262(10) 0.0128(8) 0.0013(8) 0.0028(8) N4 0.0181(9) 0.0304(10) 0.0249(10) 0.0070(8) -0.0013(8) 0.0035(8) N5 0.0230(10) 0.0273(10) 0.0280(10) 0.0017(8) -0.0004(8) 0.0005(8) N6 0.0277(10) 0.0248(10) 0.0257(10) 0.0023(8) 0.0051(8) 0.0031(8) N7 0.0258(10) 0.0243(10) 0.0220(9) 0.0008(8) 0.0039(8) -0.0005(8) N8 0.0243(10) 0.0253(10) 0.0291(10) 0.0041(8) 0.0045(8) -0.0038(8) O1 0.0264(8) 0.0285(8) 0.0233(8) 0.0110(7) -0.0022(6) -0.0006(7) O2 0.0293(9) 0.0304(9) 0.0242(8) 0.0111(7) -0.0042(7) 0.0035(7) O3 0.0363(10) 0.0210(8) 0.0232(8) 0.0007(6) -0.0054(7) -0.0022(7) O4 0.0296(9) 0.0209(8) 0.0282(8) 0.0011(7) -0.0014(7) -0.0019(6) C1 0.0214(11) 0.0217(11) 0.0209(10) 0.0075(8) -0.0019(8) -0.0016(8) C2 0.0375(14) 0.0332(14) 0.0433(15) 0.0220(12) 0.0040(12) 0.0001(11) C3 0.0194(11) 0.0335(13) 0.0341(13) 0.0159(10) 0.0036(9) 0.0071(9) C4 0.0386(16) 0.0548(18) 0.0434(16) 0.0095(14) 0.0143(13) 0.0222(14) C5 0.0232(13) 0.0448(16) 0.069(2) 0.0215(15) -0.0009(13) 0.0005(11) C6 0.0272(12) 0.0315(12) 0.0228(11) 0.0081(9) 0.0063(9) 0.0027(10) C7 0.0327(14) 0.0542(18) 0.0304(14) -0.0050(12) 0.0062(11) -0.0063(13) C8 0.0262(12) 0.0405(14) 0.0311(13) 0.0026(11) 0.0084(10) -0.0009(10) C11 0.0235(11) 0.0209(11) 0.0217(10) 0.0050(8) -0.0026(9) -0.0004(8) C12 0.0506(17) 0.0323(14) 0.0414(15) 0.0200(12) 0.0030(13) 0.0094(12) C13 0.0266(12) 0.0355(13) 0.0291(12) 0.0149(10) 0.0047(10) 0.0015(10) C14 0.084(3) 0.0470(18) 0.0451(18) 0.0140(14) 0.0360(18) 0.0122(17) C15 0.0349(15) 0.067(2) 0.0465(17) 0.0267(15) -0.0022(13) -0.0176(14) C16 0.0200(11) 0.0313(12) 0.0267(11) 0.0062(10) -0.0009(9) 0.0037(9) C17 0.0236(13) 0.0496(17) 0.0487(17) -0.0035(14) 0.0033(12) 0.0107(12) C18 0.0310(14) 0.0370(15) 0.0465(16) 0.0056(12) -0.0031(12) -0.0043(11) C21 0.0299(12) 0.0213(11) 0.0207(10) 0.0048(9) -0.0039(9) 0.0014(9) C22 0.0461(16) 0.0220(12) 0.0382(14) 0.0054(10) 0.0007(12) 0.0022(11) C23 0.0234(12) 0.0280(12) 0.0373(14) -0.0023(10) -0.0024(10) -0.0028(10) C24 0.0349(17) 0.110(3) 0.066(2) 0.053(2) 0.0051(16) 0.0127(19) C25 0.0260(15) 0.105(3) 0.059(2) 0.042(2) 0.0045(14) 0.0021(16) C26 0.0380(14) 0.0257(12) 0.0241(11) 0.0013(9) 0.0098(10) 0.0060(10) C27 0.078(2) 0.0540(19) 0.0410(17) 0.0162(14) 0.0297(17) 0.0219(17) C28 0.0523(18) 0.0583(19) 0.0376(15) 0.0095(14) 0.0118(14) 0.0303(15) C31 0.0261(12) 0.0204(11) 0.0236(11) 0.0047(9) -0.0016(9) 0.0003(9) C32 0.0420(15) 0.0214(12) 0.0345(13) 0.0040(10) 0.0020(11) -0.0011(10) C33 0.0315(13) 0.0232(11) 0.0238(11) 0.0019(9) 0.0061(10) 0.0011(9) C34 0.0384(14) 0.0336(13) 0.0307(13) 0.0102(11) 0.0031(11) -0.0013(11) C35 0.0332(14) 0.0452(15) 0.0358(14) 0.0123(12) 0.0132(11) 0.0079(12) C36 0.0269(13) 0.0297(13) 0.0425(15) 0.0044(11) 0.0093(11) -0.0051(10) C37 0.0397(16) 0.071(2) 0.0501(18) 0.0271(16) 0.0135(14) -0.0047(15) C38 0.0302(16) 0.090(3) 0.056(2) 0.0282(19) 0.0001(14) -0.0045(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.872(2) . ? Cu1 N1 1.877(2) . ? Cu1 Cu2 2.4653(4) . ? Cu2 N2 1.878(2) . ? Cu2 N4 1.879(2) . ? Cu3 N7 1.8750(19) . ? Cu3 N5 1.8753(19) . ? Cu3 Cu4 2.4732(4) . ? Cu4 N8 1.8709(19) . ? Cu4 N6 1.879(2) . ? N1 C1 1.321(3) . ? N1 C3 1.471(3) . ? N2 C1 1.324(3) . ? N2 C6 1.475(3) . ? N3 C11 1.325(3) . ? N3 C13 1.472(3) . ? N4 C11 1.322(3) . ? N4 C16 1.475(3) . ? N5 C21 1.326(3) . ? N5 C23 1.481(3) . ? N6 C21 1.317(3) . ? N6 C26 1.473(3) . ? N7 C31 1.331(3) . ? N7 C33 1.481(3) . ? N8 C31 1.320(3) . ? N8 C36 1.479(3) . ? O1 C1 1.384(3) . ? O1 C2 1.447(3) . ? O2 C11 1.382(3) . ? O2 C12 1.447(3) . ? O3 C21 1.387(3) . ? O3 C22 1.439(3) . ? O4 C31 1.377(3) . ? O4 C32 1.440(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C5 1.520(4) . ? C3 C4 1.528(4) . ? C3 H3 1.0000 . ? 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 C8 1.520(4) . ? C6 C7 1.521(4) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.513(4) . ? C13 C14 1.515(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.508(4) . ? C16 C18 1.521(4) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.505(5) . ? C23 C25 1.511(5) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C28 1.509(4) . ? C26 C27 1.513(4) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.523(4) . ? C33 C35 1.524(4) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C38 1.512(5) . ? C36 C37 1.519(4) . ? C36 H36 1.0000 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 N3 Cu1 N1 176.04(9) . . ? N3 Cu1 Cu2 88.04(6) . . ? N1 Cu1 Cu2 88.01(6) . . ? N2 Cu2 N4 175.11(9) . . ? N2 Cu2 Cu1 87.63(6) . . ? N4 Cu2 Cu1 87.54(6) . . ? N7 Cu3 N5 174.99(9) . . ? N7 Cu3 Cu4 87.31(6) . . ? N5 Cu3 Cu4 87.91(7) . . ? N8 Cu4 N6 175.33(9) . . ? N8 Cu4 Cu3 87.93(6) . . ? N6 Cu4 Cu3 87.40(6) . . ? C1 N1 C3 120.4(2) . . ? C1 N1 Cu1 119.68(16) . . ? C3 N1 Cu1 119.82(16) . . ? C1 N2 C6 118.58(19) . . ? C1 N2 Cu2 119.73(16) . . ? C6 N2 Cu2 121.51(15) . . ? C11 N3 C13 120.4(2) . . ? C11 N3 Cu1 119.75(16) . . ? C13 N3 Cu1 119.81(16) . . ? C11 N4 C16 119.7(2) . . ? C11 N4 Cu2 119.63(16) . . ? C16 N4 Cu2 120.31(16) . . ? C21 N5 C23 119.15(19) . . ? C21 N5 Cu3 119.26(16) . . ? C23 N5 Cu3 121.28(16) . . ? C21 N6 C26 120.5(2) . . ? C21 N6 Cu4 120.12(16) . . ? C26 N6 Cu4 119.39(16) . . ? C31 N7 C33 117.68(19) . . ? C31 N7 Cu3 119.73(16) . . ? C33 N7 Cu3 121.64(15) . . ? C31 N8 C36 118.8(2) . . ? C31 N8 Cu4 119.61(16) . . ? C36 N8 Cu4 121.52(16) . . ? C1 O1 C2 112.54(18) . . ? C11 O2 C12 112.23(19) . . ? C21 O3 C22 112.61(18) . . ? C31 O4 C32 113.21(19) . . ? N1 C1 N2 124.0(2) . . ? N1 C1 O1 117.7(2) . . ? N2 C1 O1 118.4(2) . . ? O1 C2 H2A 109.5 . . ? O1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C5 109.7(2) . . ? N1 C3 C4 109.1(2) . . ? C5 C3 C4 111.0(2) . . ? N1 C3 H3 109.0 . . ? C5 C3 H3 109.0 . . ? C4 C3 H3 109.0 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 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 . . ? N2 C6 C8 109.2(2) . . ? N2 C6 C7 110.7(2) . . ? C8 C6 C7 109.7(2) . . ? N2 C6 H6 109.1 . . ? C8 C6 H6 109.1 . . ? C7 C6 H6 109.1 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N4 C11 N3 123.8(2) . . ? N4 C11 O2 119.1(2) . . ? N3 C11 O2 117.1(2) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C15 109.0(2) . . ? N3 C13 C14 109.7(2) . . ? C15 C13 C14 112.0(3) . . ? N3 C13 H13 108.7 . . ? C15 C13 H13 108.7 . . ? C14 C13 H13 108.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N4 C16 C17 111.1(2) . . ? N4 C16 C18 109.0(2) . . ? C17 C16 C18 110.8(2) . . ? N4 C16 H16 108.6 . . ? C17 C16 H16 108.6 . . ? C18 C16 H16 108.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N6 C21 N5 124.1(2) . . ? N6 C21 O3 117.7(2) . . ? N5 C21 O3 118.2(2) . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 C24 110.2(2) . . ? N5 C23 C25 109.9(2) . . ? C24 C23 C25 110.0(3) . . ? N5 C23 H23 108.9 . . ? C24 C23 H23 108.9 . . ? C25 C23 H23 108.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 C28 109.5(2) . . ? N6 C26 C27 110.0(2) . . ? C28 C26 C27 111.8(3) . . ? N6 C26 H26 108.5 . . ? C28 C26 H26 108.5 . . ? C27 C26 H26 108.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N8 C31 N7 123.8(2) . . ? N8 C31 O4 117.8(2) . . ? N7 C31 O4 118.4(2) . . ? O4 C32 H32A 109.5 . . ? O4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N7 C33 C34 110.3(2) . . ? N7 C33 C35 109.7(2) . . ? C34 C33 C35 110.7(2) . . ? N7 C33 H33 108.7 . . ? C34 C33 H33 108.7 . . ? C35 C33 H33 108.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N8 C36 C38 110.6(2) . . ? N8 C36 C37 109.5(2) . . ? C38 C36 C37 110.8(3) . . ? N8 C36 H36 108.6 . . ? C38 C36 H36 108.6 . . ? C37 C36 H36 108.6 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.756 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.079 data_2 _database_code_depnum_ccdc_archive 'CCDC 901462' #TrackingRef 'Full Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H38 Cu2 N4 O2' _chemical_formula_weight 469.60 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' O O 0.0106 0.0060 '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' 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 6.9630(2) _cell_length_b 16.1930(5) _cell_length_c 10.4080(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.5790(10) _cell_angle_gamma 90.00 _cell_volume 1149.64(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2633 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 27.56 _exptl_crystal_description block _exptl_crystal_colour colourles _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.867 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7064 _exptl_absorpt_correction_T_max 0.8353 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21623 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.56 _reflns_number_total 2633 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _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^)+(0.0353P)^2^+0.5867P] 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 2633 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 1.00396(3) 0.440133(15) 0.57439(2) 0.02708(10) Uani 1 1 d . . . O1 O 0.53463(19) 0.41156(9) 0.27253(14) 0.0295(3) Uani 1 1 d . . . N1 N 0.7807(2) 0.40036(10) 0.45899(17) 0.0284(4) Uani 1 1 d . . . N2 N 0.7728(2) 0.51345(10) 0.31951(16) 0.0277(4) Uani 1 1 d . . . C1 C 0.7003(3) 0.44297(12) 0.3537(2) 0.0248(4) Uani 1 1 d . . . C2 C 0.7029(3) 0.31786(13) 0.4830(2) 0.0342(5) Uani 1 1 d . . . H2 H 0.5891 0.3054 0.4104 0.041 Uiso 1 1 calc R . . C3 C 0.8592(4) 0.25381(16) 0.4810(3) 0.0562(7) Uani 1 1 d . . . H3A H 0.8964 0.2541 0.3950 0.084 Uiso 1 1 calc R . . H3B H 0.8086 0.1992 0.4974 0.084 Uiso 1 1 calc R . . H3C H 0.9743 0.2665 0.5493 0.084 Uiso 1 1 calc R . . C4 C 0.6320(6) 0.31791(19) 0.6099(3) 0.0712(9) Uani 1 1 d . . . H4A H 0.7420 0.3297 0.6824 0.107 Uiso 1 1 calc R . . H4B H 0.5766 0.2637 0.6233 0.107 Uiso 1 1 calc R . . H4C H 0.5309 0.3604 0.6068 0.107 Uiso 1 1 calc R . . C5 C 0.6856(3) 0.54943(13) 0.1899(2) 0.0318(5) Uani 1 1 d . . . H5 H 0.5397 0.5445 0.1757 0.038 Uiso 1 1 calc R . . C6 C 0.7392(4) 0.63993(15) 0.1874(2) 0.0451(6) Uani 1 1 d . . . H6A H 0.6950 0.6689 0.2589 0.068 Uiso 1 1 calc R . . H6B H 0.6756 0.6641 0.1032 0.068 Uiso 1 1 calc R . . H6C H 0.8817 0.6454 0.1983 0.068 Uiso 1 1 calc R . . C7 C 0.7565(4) 0.50283(18) 0.0812(2) 0.0466(6) Uani 1 1 d . . . H7A H 0.8994 0.5075 0.0939 0.070 Uiso 1 1 calc R . . H7B H 0.6958 0.5265 -0.0040 0.070 Uiso 1 1 calc R . . H7C H 0.7199 0.4445 0.0836 0.070 Uiso 1 1 calc R . . C8 C 0.3538(3) 0.43445(14) 0.3129(2) 0.0344(5) Uani 1 1 d . . . H8A H 0.3132 0.4906 0.2811 0.041 Uiso 1 1 calc R . . H8B H 0.3734 0.4342 0.4098 0.041 Uiso 1 1 calc R . . C9 C 0.1994(3) 0.37303(15) 0.2558(3) 0.0412(5) Uani 1 1 d . . . H9A H 0.1871 0.3711 0.1604 0.062 Uiso 1 1 calc R . . H9B H 0.0737 0.3895 0.2767 0.062 Uiso 1 1 calc R . . H9C H 0.2363 0.3183 0.2929 0.062 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 0.02649(15) 0.02588(15) 0.02820(15) 0.00050(9) 0.00390(10) -0.00494(9) O1 0.0222(7) 0.0322(7) 0.0340(8) -0.0087(6) 0.0051(6) -0.0024(6) N1 0.0274(8) 0.0230(9) 0.0345(9) 0.0000(7) 0.0060(7) -0.0051(7) N2 0.0276(8) 0.0287(9) 0.0266(9) 0.0003(7) 0.0048(7) -0.0032(7) C1 0.0211(9) 0.0270(10) 0.0271(10) -0.0068(8) 0.0063(8) -0.0006(7) C2 0.0337(11) 0.0270(11) 0.0408(12) 0.0002(9) 0.0048(9) -0.0086(9) C3 0.0560(16) 0.0317(13) 0.082(2) 0.0016(13) 0.0157(15) 0.0003(12) C4 0.101(3) 0.0499(17) 0.077(2) -0.0008(15) 0.0515(19) -0.0261(17) C5 0.0262(10) 0.0374(12) 0.0309(11) 0.0042(9) 0.0037(9) 0.0009(8) C6 0.0478(14) 0.0427(14) 0.0431(13) 0.0117(11) 0.0052(11) -0.0047(11) C7 0.0467(14) 0.0624(17) 0.0308(13) -0.0011(11) 0.0086(11) 0.0034(12) C8 0.0251(10) 0.0356(12) 0.0438(13) -0.0079(9) 0.0096(9) -0.0001(8) C9 0.0269(11) 0.0378(13) 0.0589(15) -0.0020(11) 0.0086(10) -0.0053(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.8739(16) 3_766 ? Cu1 N1 1.8773(17) . ? Cu1 Cu1 2.4750(5) 3_766 ? O1 C1 1.383(2) . ? O1 C8 1.453(2) . ? N1 C1 1.321(3) . ? N1 C2 1.482(3) . ? N2 C1 1.325(3) . ? N2 C5 1.483(3) . ? N2 Cu1 1.8739(16) 3_766 ? C2 C4 1.499(4) . ? C2 C3 1.507(3) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.514(3) . ? C5 C7 1.523(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.497(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 N2 Cu1 N1 175.58(7) 3_766 . ? N2 Cu1 Cu1 88.06(5) 3_766 3_766 ? N1 Cu1 Cu1 87.53(5) . 3_766 ? C1 O1 C8 113.23(15) . . ? C1 N1 C2 120.18(17) . . ? C1 N1 Cu1 120.69(13) . . ? C2 N1 Cu1 119.02(13) . . ? C1 N2 C5 118.30(17) . . ? C1 N2 Cu1 120.19(14) . 3_766 ? C5 N2 Cu1 121.21(13) . 3_766 ? N1 C1 N2 123.49(18) . . ? N1 C1 O1 118.53(17) . . ? N2 C1 O1 117.96(17) . . ? N1 C2 C4 110.15(19) . . ? N1 C2 C3 109.20(18) . . ? C4 C2 C3 112.3(2) . . ? N1 C2 H2 108.4 . . ? C4 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 109.82(18) . . ? N2 C5 C7 110.30(18) . . ? C6 C5 C7 110.4(2) . . ? N2 C5 H5 108.8 . . ? C6 C5 H5 108.8 . . ? C7 C5 H5 108.8 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C8 C9 108.09(17) . . ? O1 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O1 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.651 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.129 data_3 _database_code_depnum_ccdc_archive 'CCDC 901463' #TrackingRef 'Full Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H42 Cu2 N4 O2' _chemical_formula_weight 497.66 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 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 14.26300(10) _cell_length_b 10.37000(10) _cell_length_c 18.3100(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.89 _cell_angle_gamma 90.00 _cell_volume 2530.17(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7717 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 30.52 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.701 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7272 _exptl_absorpt_correction_T_max 0.7845 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 52560 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.52 _reflns_number_total 7717 _reflns_number_gt 6446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0361P)^2^+0.8289P] 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 SHELXL _refine_ls_extinction_coef 0.0024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7717 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0751 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.271500(13) 0.067456(16) 0.066059(9) 0.02474(5) Uani 1 1 d . . . Cu2 Cu 0.229718(13) -0.040462(16) 0.169587(10) 0.02678(6) Uani 1 1 d . . . N1 N 0.31858(9) 0.20769(11) 0.13457(6) 0.0254(2) Uani 1 1 d . . . N2 N 0.28310(9) 0.10230(12) 0.23365(7) 0.0273(2) Uani 1 1 d . . . N3 N 0.17838(9) -0.17775(11) 0.10071(7) 0.0268(2) Uani 1 1 d . . . N4 N 0.22116(9) -0.07808(11) 0.00324(7) 0.0260(2) Uani 1 1 d . . . O1 O 0.35470(7) 0.30518(9) 0.25655(6) 0.0270(2) Uani 1 1 d . . . O2 O 0.14236(7) -0.27714(9) -0.02019(6) 0.0273(2) Uani 1 1 d . . . C1 C 0.31881(9) 0.20188(12) 0.20707(7) 0.0225(2) Uani 1 1 d . . . C2 C 0.18099(9) -0.17449(12) 0.02929(8) 0.0234(2) Uani 1 1 d . A . C11 C 0.33911(12) 0.33033(14) 0.10244(9) 0.0325(3) Uani 1 1 d . . . H11 H 0.3688 0.3926 0.1463 0.039 Uiso 1 1 calc R . . C12 C 0.41362(16) 0.30807(19) 0.06160(13) 0.0520(5) Uani 1 1 d . . . H12A H 0.4758 0.2719 0.0988 0.078 Uiso 1 1 calc R . . H12B H 0.4283 0.3902 0.0415 0.078 Uiso 1 1 calc R . . H12C H 0.3849 0.2477 0.0181 0.078 Uiso 1 1 calc R . . C13 C 0.24100(15) 0.38598(17) 0.04586(11) 0.0449(4) Uani 1 1 d . . . H13A H 0.2112 0.3253 0.0027 0.067 Uiso 1 1 calc R . . H13B H 0.2545 0.4681 0.0250 0.067 Uiso 1 1 calc R . . H13C H 0.1944 0.4002 0.0735 0.067 Uiso 1 1 calc R . . C14 C 0.27770(12) 0.10405(15) 0.31266(8) 0.0328(3) Uani 1 1 d . . . H14 H 0.3222 0.1742 0.3439 0.039 Uiso 1 1 calc R . . C15 C 0.3128(2) -0.0238(2) 0.35307(11) 0.0577(5) Uani 1 1 d . . . H15A H 0.2697 -0.0931 0.3226 0.087 Uiso 1 1 calc R . . H15B H 0.3090 -0.0215 0.4055 0.087 Uiso 1 1 calc R . . H15C H 0.3822 -0.0396 0.3573 0.087 Uiso 1 1 calc R . . C16 C 0.17048(14) 0.13133(19) 0.30611(11) 0.0452(4) Uani 1 1 d . . . H16A H 0.1496 0.2154 0.2812 0.068 Uiso 1 1 calc R . . H16B H 0.1664 0.1322 0.3584 0.068 Uiso 1 1 calc R . . H16C H 0.1262 0.0640 0.2745 0.068 Uiso 1 1 calc R . . C17 C 0.46348(11) 0.32129(17) 0.28644(9) 0.0367(3) Uani 1 1 d . . . H17 H 0.4890 0.3101 0.2426 0.044 Uiso 1 1 calc R . . C18 C 0.51401(14) 0.2242(2) 0.34986(12) 0.0559(5) Uani 1 1 d . . . H18A H 0.4893 0.2350 0.3930 0.084 Uiso 1 1 calc R . . H18B H 0.5868 0.2379 0.3691 0.084 Uiso 1 1 calc R . . H18C H 0.4987 0.1368 0.3286 0.084 Uiso 1 1 calc R . . C19 C 0.48188(15) 0.45792(19) 0.31576(14) 0.0564(5) Uani 1 1 d . . . H19A H 0.4444 0.5171 0.2738 0.085 Uiso 1 1 calc R . . H19B H 0.5537 0.4772 0.3324 0.085 Uiso 1 1 calc R . . H19C H 0.4595 0.4684 0.3602 0.085 Uiso 1 1 calc R . . C21 C 0.14378(12) -0.29319(14) 0.13047(9) 0.0328(3) Uani 1 1 d . . . H21 H 0.1133 -0.3541 0.0860 0.039 Uiso 1 1 calc R . . C22 C 0.23317(17) -0.35909(19) 0.19107(12) 0.0536(5) Uani 1 1 d . . . H22A H 0.2826 -0.3819 0.1673 0.080 Uiso 1 1 calc R . . H22B H 0.2106 -0.4374 0.2098 0.080 Uiso 1 1 calc R . . H22C H 0.2639 -0.3004 0.2351 0.080 Uiso 1 1 calc R . . C23 C 0.06491(18) -0.2570(2) 0.16387(16) 0.0666(7) Uani 1 1 d . . . H23A H 0.0925 -0.1931 0.2055 0.100 Uiso 1 1 calc R . . H23B H 0.0443 -0.3340 0.1853 0.100 Uiso 1 1 calc R . . H23C H 0.0066 -0.2203 0.1225 0.100 Uiso 1 1 calc R . . C24 C 0.23434(12) -0.08807(14) -0.07274(8) 0.0301(3) Uani 1 1 d . . . H24 H 0.1863 -0.1540 -0.1052 0.036 Uiso 1 1 calc R . . C25 C 0.34006(15) -0.1316(2) -0.06083(12) 0.0552(5) Uani 1 1 d . . . H25A H 0.3881 -0.0700 -0.0269 0.083 Uiso 1 1 calc R . . H25B H 0.3488 -0.1358 -0.1115 0.083 Uiso 1 1 calc R . . H25C H 0.3517 -0.2170 -0.0364 0.083 Uiso 1 1 calc R . . C26 C 0.2114(2) 0.03994(19) -0.11504(12) 0.0616(6) Uani 1 1 d . . . H26A H 0.1409 0.0625 -0.1259 0.092 Uiso 1 1 calc R . . H26B H 0.2234 0.0334 -0.1643 0.092 Uiso 1 1 calc R . . H26C H 0.2548 0.1068 -0.0822 0.092 Uiso 1 1 calc R . . C27 C 0.0345(3) -0.2832(5) -0.0567(3) 0.0336(8) Uani 0.689(14) 1 d P A -1 H27 H 0.0062 -0.3115 -0.0166 0.040 Uiso 0.689(14) 1 calc PR A -1 C28 C -0.0124(3) -0.1564(4) -0.0899(4) 0.0603(15) Uani 0.689(14) 1 d P A -1 H28A H 0.0043 -0.0918 -0.0481 0.090 Uiso 0.689(14) 1 calc PR A -1 H28B H -0.0855 -0.1664 -0.1128 0.090 Uiso 0.689(14) 1 calc PR A -1 H28C H 0.0132 -0.1282 -0.1303 0.090 Uiso 0.689(14) 1 calc PR A -1 C29 C 0.0190(10) -0.3874(12) -0.1144(7) 0.062(3) Uani 0.689(14) 1 d P A -1 H29A H 0.0482 -0.3624 -0.1533 0.093 Uiso 0.689(14) 1 calc PR A -1 H29B H -0.0531 -0.4029 -0.1405 0.093 Uiso 0.689(14) 1 calc PR A -1 H29C H 0.0515 -0.4663 -0.0878 0.093 Uiso 0.689(14) 1 calc PR A -1 C28B C -0.0313(7) -0.1921(14) -0.0515(10) 0.066(4) Uani 0.311(14) 1 d P A -2 H28D H -0.0473 -0.2496 -0.0151 0.099 Uiso 0.311(14) 1 calc PR A -2 H28E H -0.0928 -0.1724 -0.0958 0.099 Uiso 0.311(14) 1 calc PR A -2 H28F H -0.0022 -0.1119 -0.0246 0.099 Uiso 0.311(14) 1 calc PR A -2 C27B C 0.0418(9) -0.2560(10) -0.0804(7) 0.038(2) Uani 0.311(14) 1 d P A -2 H27B H 0.0512 -0.1978 -0.1208 0.046 Uiso 0.311(14) 1 calc PR A -2 C29B C 0.001(2) -0.387(2) -0.1217(14) 0.040(3) Uani 0.311(14) 1 d P A -2 H29D H 0.0498 -0.4232 -0.1429 0.060 Uiso 0.311(14) 1 calc PR A -2 H29E H -0.0629 -0.3727 -0.1643 0.060 Uiso 0.311(14) 1 calc PR A -2 H29F H -0.0083 -0.4473 -0.0838 0.060 Uiso 0.311(14) 1 calc PR A -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 0.03091(9) 0.02348(9) 0.01962(8) -0.00293(6) 0.00875(7) -0.00365(6) Cu2 0.03458(10) 0.02516(9) 0.02209(9) -0.00417(6) 0.01195(7) -0.00625(6) N1 0.0291(6) 0.0241(5) 0.0220(5) -0.0025(4) 0.0080(4) -0.0037(4) N2 0.0323(6) 0.0285(6) 0.0221(5) -0.0054(4) 0.0111(5) -0.0044(5) N3 0.0322(6) 0.0230(5) 0.0264(6) -0.0030(4) 0.0119(5) -0.0050(4) N4 0.0322(6) 0.0254(5) 0.0208(5) -0.0034(4) 0.0096(5) -0.0017(4) O1 0.0213(4) 0.0297(5) 0.0281(5) -0.0103(4) 0.0064(4) -0.0045(4) O2 0.0240(4) 0.0245(5) 0.0297(5) -0.0087(4) 0.0052(4) 0.0001(4) C1 0.0183(5) 0.0241(6) 0.0226(6) -0.0045(5) 0.0041(5) 0.0007(4) C2 0.0218(6) 0.0212(6) 0.0246(6) -0.0041(5) 0.0052(5) 0.0013(5) C11 0.0426(8) 0.0269(7) 0.0296(7) -0.0032(5) 0.0148(6) -0.0084(6) C12 0.0563(11) 0.0492(11) 0.0642(12) -0.0003(9) 0.0383(10) -0.0133(9) C13 0.0626(11) 0.0334(8) 0.0386(9) 0.0085(7) 0.0179(8) 0.0046(8) C14 0.0465(8) 0.0320(7) 0.0221(6) -0.0057(5) 0.0150(6) -0.0047(6) C15 0.0963(17) 0.0480(11) 0.0292(9) 0.0072(8) 0.0229(10) 0.0154(11) C16 0.0550(10) 0.0489(10) 0.0424(9) -0.0114(8) 0.0305(8) -0.0093(8) C17 0.0214(6) 0.0532(10) 0.0340(8) -0.0143(7) 0.0079(6) -0.0087(6) C18 0.0307(8) 0.0672(13) 0.0552(12) -0.0087(10) -0.0023(8) 0.0072(8) C19 0.0412(10) 0.0524(11) 0.0658(13) -0.0182(10) 0.0072(9) -0.0209(8) C21 0.0399(8) 0.0274(7) 0.0348(7) -0.0049(6) 0.0177(6) -0.0103(6) C22 0.0708(13) 0.0419(10) 0.0435(10) 0.0125(8) 0.0148(9) -0.0035(9) C23 0.0721(14) 0.0557(12) 0.1003(18) -0.0142(12) 0.0655(14) -0.0197(11) C24 0.0403(8) 0.0296(7) 0.0207(6) -0.0036(5) 0.0110(6) -0.0014(6) C25 0.0516(11) 0.0796(15) 0.0417(10) 0.0028(9) 0.0255(9) 0.0106(10) C26 0.1088(19) 0.0479(11) 0.0362(10) 0.0125(8) 0.0358(11) 0.0223(11) C27 0.0234(12) 0.038(2) 0.034(2) -0.0110(15) 0.0032(14) -0.0016(12) C28 0.0291(16) 0.0517(19) 0.077(3) -0.0142(19) -0.0089(17) 0.0075(13) C29 0.030(4) 0.064(4) 0.074(4) -0.040(3) -0.005(3) -0.007(2) C28B 0.031(3) 0.071(7) 0.077(7) -0.036(6) -0.004(4) 0.014(4) C27B 0.033(4) 0.035(4) 0.032(5) -0.006(3) -0.007(3) -0.003(3) C29B 0.025(7) 0.036(5) 0.048(5) -0.025(4) -0.001(5) -0.010(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 N4 1.8781(11) . ? Cu1 N1 1.8811(11) . ? Cu1 Cu2 2.4508(2) . ? Cu2 N3 1.8695(11) . ? Cu2 N2 1.8736(12) . ? N1 C1 1.3277(17) . ? N1 C11 1.4738(18) . ? N2 C1 1.3189(18) . ? N2 C14 1.4760(17) . ? N3 C2 1.3217(17) . ? N3 C21 1.4716(18) . ? N4 C2 1.3229(18) . ? N4 C24 1.4725(17) . ? O1 C1 1.3783(15) . ? O1 C17 1.4592(16) . ? O2 C2 1.3790(15) . ? O2 C27 1.444(4) . ? O2 C27B 1.481(10) . ? C11 C12 1.519(2) . ? C11 C13 1.527(2) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.514(2) . ? C14 C16 1.517(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.505(2) . ? C17 C18 1.512(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C23 1.507(2) . ? C21 C22 1.521(3) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C26 1.513(2) . ? C24 C25 1.513(2) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.471(13) . ? C27 C28 1.502(9) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C28B C27B 1.48(2) . ? C28B H28D 0.9800 . ? C28B H28E 0.9800 . ? C28B H28F 0.9800 . ? C27B C29B 1.56(2) . ? C27B H27B 1.0000 . ? C29B H29D 0.9800 . ? C29B H29E 0.9800 . ? C29B H29F 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 N4 Cu1 N1 175.74(5) . . ? N4 Cu1 Cu2 87.79(4) . . ? N1 Cu1 Cu2 87.97(3) . . ? N3 Cu2 N2 176.42(5) . . ? N3 Cu2 Cu1 88.32(4) . . ? N2 Cu2 Cu1 88.10(4) . . ? C1 N1 C11 120.55(11) . . ? C1 N1 Cu1 120.31(9) . . ? C11 N1 Cu1 118.38(9) . . ? C1 N2 C14 120.93(12) . . ? C1 N2 Cu2 120.79(9) . . ? C14 N2 Cu2 118.15(9) . . ? C2 N3 C21 121.24(11) . . ? C2 N3 Cu2 120.37(9) . . ? C21 N3 Cu2 118.17(9) . . ? C2 N4 C24 120.34(11) . . ? C2 N4 Cu1 120.44(9) . . ? C24 N4 Cu1 119.04(9) . . ? C1 O1 C17 115.57(10) . . ? C2 O2 C27 116.62(19) . . ? C2 O2 C27B 115.4(4) . . ? C27 O2 C27B 21.9(4) . . ? N2 C1 N1 122.74(12) . . ? N2 C1 O1 117.89(11) . . ? N1 C1 O1 119.34(12) . . ? N3 C2 N4 122.99(12) . . ? N3 C2 O2 118.99(12) . . ? N4 C2 O2 118.00(12) . . ? N1 C11 C12 109.80(13) . . ? N1 C11 C13 109.42(13) . . ? C12 C11 C13 110.87(15) . . ? N1 C11 H11 108.9 . . ? C12 C11 H11 108.9 . . ? C13 C11 H11 108.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C15 110.16(13) . . ? N2 C14 C16 109.15(13) . . ? C15 C14 C16 110.48(16) . . ? N2 C14 H14 109.0 . . ? C15 C14 H14 109.0 . . ? C16 C14 H14 109.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 C19 105.58(13) . . ? O1 C17 C18 111.34(14) . . ? C19 C17 C18 112.23(15) . . ? O1 C17 H17 109.2 . . ? C19 C17 H17 109.2 . . ? C18 C17 H17 109.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C21 C23 110.18(14) . . ? N3 C21 C22 109.33(13) . . ? C23 C21 C22 111.63(17) . . ? N3 C21 H21 108.5 . . ? C23 C21 H21 108.5 . . ? C22 C21 H21 108.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N4 C24 C26 110.16(13) . . ? N4 C24 C25 109.94(12) . . ? C26 C24 C25 110.99(16) . . ? N4 C24 H24 108.6 . . ? C26 C24 H24 108.6 . . ? C25 C24 H24 108.6 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 C27 C29 103.1(6) . . ? O2 C27 C28 113.4(5) . . ? C29 C27 C28 115.0(7) . . ? O2 C27 H27 108.4 . . ? C29 C27 H27 108.4 . . ? C28 C27 H27 108.4 . . ? C27B C28B H28D 109.5 . . ? C27B C28B H28E 109.5 . . ? H28D C28B H28E 109.5 . . ? C27B C28B H28F 109.5 . . ? H28D C28B H28F 109.5 . . ? H28E C28B H28F 109.5 . . ? O2 C27B C28B 114.7(11) . . ? O2 C27B C29B 108.9(11) . . ? C28B C27B C29B 112.1(16) . . ? O2 C27B H27B 106.9 . . ? C28B C27B H27B 106.9 . . ? C29B C27B H27B 106.9 . . ? C27B C29B H29D 109.5 . . ? C27B C29B H29E 109.5 . . ? H29D C29B H29E 109.5 . . ? C27B C29B H29F 109.5 . . ? H29D C29B H29F 109.5 . . ? H29E C29B H29F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.402 _refine_diff_density_min -0.686 _refine_diff_density_rms 0.119 data_4 _database_code_depnum_ccdc_archive 'CCDC 901464' #TrackingRef 'Full Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H46 Cu2 N4 O2' _chemical_formula_weight 525.71 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 Pcab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 11.0610(2) _cell_length_b 12.9330(2) _cell_length_c 18.2690(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2613.42(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3244 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 28.28 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.651 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7337 _exptl_absorpt_correction_T_max 0.8140 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; This crystal was weakly diffracting and there was no observable data above the 2theta limit recorded. ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 40255 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3244 _reflns_number_gt 2684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0342P)^2^+0.8296P] 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 SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3244 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 1.013473(17) 0.036811(13) -0.060512(9) 0.01999(8) Uani 1 1 d . . . N1 N 0.91456(11) 0.14691(9) -0.03022(6) 0.0200(3) Uani 1 1 d . . . N2 N 0.88988(11) 0.07737(9) 0.08559(6) 0.0201(3) Uani 1 1 d . . . O1 O 0.79088(9) 0.23091(7) 0.05453(5) 0.0193(2) Uani 1 1 d . . . C1 C 0.86919(12) 0.15156(10) 0.03676(8) 0.0181(3) Uani 1 1 d . . . C2 C 0.88536(14) 0.22519(12) -0.08577(8) 0.0235(3) Uani 1 1 d . . . H2 H 0.8298 0.2777 -0.0638 0.028 Uiso 1 1 calc R . . C3 C 0.82223(17) 0.17382(14) -0.15042(9) 0.0360(4) Uani 1 1 d . . . H3A H 0.8760 0.1219 -0.1721 0.054 Uiso 1 1 calc R . . H3B H 0.8023 0.2262 -0.1872 0.054 Uiso 1 1 calc R . . H3C H 0.7479 0.1403 -0.1335 0.054 Uiso 1 1 calc R . . C4 C 1.00074(16) 0.27877(14) -0.11062(11) 0.0368(4) Uani 1 1 d . . . H4A H 1.0427 0.3076 -0.0680 0.055 Uiso 1 1 calc R . . H4B H 0.9805 0.3346 -0.1447 0.055 Uiso 1 1 calc R . . H4C H 1.0534 0.2286 -0.1351 0.055 Uiso 1 1 calc R . . C5 C 0.82567(13) 0.07566(12) 0.15609(8) 0.0210(3) Uani 1 1 d . . . H5 H 0.7935 0.1464 0.1665 0.025 Uiso 1 1 calc R . . C6 C 0.91292(16) 0.04519(13) 0.21675(8) 0.0290(4) Uani 1 1 d . . . H6A H 0.8716 0.0492 0.2641 0.043 Uiso 1 1 calc R . . H6B H 0.9822 0.0924 0.2167 0.043 Uiso 1 1 calc R . . H6C H 0.9412 -0.0257 0.2086 0.043 Uiso 1 1 calc R . . C7 C 0.72014(15) -0.00040(14) 0.15290(9) 0.0306(4) Uani 1 1 d . . . H7A H 0.6641 0.0205 0.1141 0.046 Uiso 1 1 calc R . . H7B H 0.6777 -0.0005 0.2000 0.046 Uiso 1 1 calc R . . H7C H 0.7509 -0.0700 0.1426 0.046 Uiso 1 1 calc R . . C8 C 0.83175(14) 0.32617(11) 0.09257(8) 0.0222(3) Uani 1 1 d . . . C9 C 0.95294(15) 0.31136(13) 0.13022(11) 0.0338(4) Uani 1 1 d . . . H9A H 0.9453 0.2582 0.1682 0.051 Uiso 1 1 calc R . . H9B H 0.9783 0.3767 0.1526 0.051 Uiso 1 1 calc R . . H9C H 1.0134 0.2896 0.0941 0.051 Uiso 1 1 calc R . . C10 C 0.83961(18) 0.41389(12) 0.03734(10) 0.0351(4) Uani 1 1 d . . . H10A H 0.9074 0.4014 0.0040 0.053 Uiso 1 1 calc R . . H10B H 0.8523 0.4794 0.0632 0.053 Uiso 1 1 calc R . . H10C H 0.7642 0.4174 0.0093 0.053 Uiso 1 1 calc R . . C11 C 0.73079(15) 0.35044(12) 0.14616(9) 0.0303(4) Uani 1 1 d . . . H11A H 0.6544 0.3575 0.1195 0.045 Uiso 1 1 calc R . . H11B H 0.7489 0.4152 0.1717 0.045 Uiso 1 1 calc R . . H11C H 0.7239 0.2942 0.1819 0.045 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 0.02656(12) 0.01777(11) 0.01564(12) 0.00171(6) 0.00483(7) 0.00635(7) N1 0.0249(6) 0.0181(6) 0.0171(6) 0.0025(5) 0.0033(5) 0.0048(5) N2 0.0256(6) 0.0188(6) 0.0160(6) 0.0009(5) 0.0045(5) 0.0042(5) O1 0.0195(5) 0.0165(5) 0.0219(5) -0.0040(4) 0.0011(4) 0.0029(4) C1 0.0171(6) 0.0160(6) 0.0211(7) -0.0022(5) 0.0005(5) 0.0003(5) C2 0.0286(8) 0.0214(7) 0.0205(7) 0.0049(6) 0.0040(6) 0.0070(6) C3 0.0448(10) 0.0382(10) 0.0250(8) -0.0006(7) -0.0056(7) 0.0139(8) C4 0.0423(10) 0.0273(9) 0.0408(10) 0.0114(8) 0.0151(8) 0.0037(7) C5 0.0254(7) 0.0204(7) 0.0171(7) 0.0000(5) 0.0060(6) 0.0020(6) C6 0.0313(9) 0.0375(9) 0.0181(7) 0.0020(6) 0.0031(6) 0.0015(7) C7 0.0283(9) 0.0350(9) 0.0284(8) -0.0011(7) 0.0065(7) -0.0040(7) C8 0.0253(7) 0.0170(7) 0.0245(7) -0.0049(6) 0.0012(6) 0.0017(5) C9 0.0272(8) 0.0263(8) 0.0479(10) -0.0080(8) -0.0062(8) -0.0014(7) C10 0.0510(11) 0.0180(8) 0.0362(9) -0.0005(7) 0.0081(8) 0.0020(7) C11 0.0331(9) 0.0245(8) 0.0332(9) -0.0094(7) 0.0078(7) 0.0016(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 N1 1.8791(12) . ? Cu1 N2 1.8798(12) 5_755 ? Cu1 Cu1 2.4257(3) 5_755 ? N1 C1 1.3240(18) . ? N1 C2 1.4695(18) . ? N2 C1 1.3299(19) . ? N2 C5 1.4711(17) . ? N2 Cu1 1.8797(12) 5_755 ? O1 C1 1.3816(16) . ? O1 C8 1.4850(16) . ? C2 C4 1.521(2) . ? C2 C3 1.524(2) . ? C5 C6 1.521(2) . ? C5 C7 1.528(2) . ? C8 C11 1.518(2) . ? C8 C9 1.519(2) . ? C8 C10 1.521(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 176.59(5) . 5_755 ? N1 Cu1 Cu1 87.56(4) . 5_755 ? N2 Cu1 Cu1 89.06(4) 5_755 5_755 ? C1 N1 C2 121.58(12) . . ? C1 N1 Cu1 121.83(10) . . ? C2 N1 Cu1 116.53(9) . . ? C1 N2 C5 121.00(12) . . ? C1 N2 Cu1 120.08(10) . 5_755 ? C5 N2 Cu1 118.43(9) . 5_755 ? C1 O1 C8 122.37(11) . . ? N1 C1 N2 121.46(13) . . ? N1 C1 O1 119.24(12) . . ? N2 C1 O1 119.10(12) . . ? N1 C2 C4 109.60(13) . . ? N1 C2 C3 109.60(13) . . ? C4 C2 C3 110.58(14) . . ? N2 C5 C6 109.60(12) . . ? N2 C5 C7 110.19(12) . . ? C6 C5 C7 110.23(13) . . ? O1 C8 C11 104.44(12) . . ? O1 C8 C9 112.09(12) . . ? C11 C8 C9 112.54(13) . . ? O1 C8 C10 109.01(12) . . ? C11 C8 C10 108.41(13) . . ? C9 C8 C10 110.13(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.459 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.095 data_k09alj19 _database_code_depnum_ccdc_archive 'CCDC 901465' #TrackingRef 'Full Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H50 Cu2 N4 O2' _chemical_formula_weight 601.80 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 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 10.2090(4) _cell_length_b 11.2920(4) _cell_length_c 13.1660(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.123(2) _cell_angle_gamma 90.00 _cell_volume 1442.48(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3043 _cell_measurement_theta_min 7.88 _cell_measurement_theta_max 27.90 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 1.505 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8640 _exptl_absorpt_correction_T_max 0.9562 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Kappa CCD Diffractometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11671 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 7.88 _diffrn_reflns_theta_max 27.90 _reflns_number_total 3043 _reflns_number_gt 2109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0250P)^2^+1.2061P] 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 3043 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 1.08948(4) 0.47583(3) 0.08457(3) 0.03146(15) Uani 1 1 d . . . N1 N 0.9624(2) 0.3763(2) 0.11873(18) 0.0303(6) Uani 1 1 d . . . N2 N 0.7927(2) 0.4235(2) -0.04044(18) 0.0288(6) Uani 1 1 d . . . O1 O 0.7452(2) 0.29119(18) 0.07943(16) 0.0309(5) Uani 1 1 d . . . C1 C 0.8364(3) 0.3651(3) 0.0518(2) 0.0283(6) Uani 1 1 d . . . C2 C 0.7426(4) 0.1740(3) 0.0373(3) 0.0388(8) Uani 1 1 d . . . H2A H 0.7252 0.1782 -0.0402 0.058 Uiso 1 1 calc R . . H2B H 0.6693 0.1281 0.0523 0.058 Uiso 1 1 calc R . . H2C H 0.8316 0.1354 0.0708 0.058 Uiso 1 1 calc R . . C3 C 0.6481(3) 0.4120(3) -0.1096(2) 0.0286(6) Uani 1 1 d . . . H3 H 0.5986 0.3555 -0.0758 0.034 Uiso 1 1 calc R . . C4 C 0.5768(3) 0.5322(3) -0.1224(3) 0.0358(7) Uani 1 1 d . . . H4A H 0.5741 0.5598 -0.0517 0.043 Uiso 1 1 calc R . . H4B H 0.6308 0.5902 -0.1492 0.043 Uiso 1 1 calc R . . C5 C 0.6446(3) 0.3644(3) -0.2188(2) 0.0362(7) Uani 1 1 d . . . H5A H 0.6880 0.2851 -0.2102 0.043 Uiso 1 1 calc R . . H5B H 0.6984 0.4176 -0.2506 0.043 Uiso 1 1 calc R . . C6 C 0.4308(3) 0.5270(3) -0.1991(3) 0.0391(8) Uani 1 1 d . . . H6A H 0.3732 0.4781 -0.1672 0.047 Uiso 1 1 calc R . . H6B H 0.3916 0.6080 -0.2097 0.047 Uiso 1 1 calc R . . C7 C 0.4969(3) 0.3557(3) -0.2937(3) 0.0399(8) Uani 1 1 d . . . H7A H 0.4976 0.3271 -0.3646 0.048 Uiso 1 1 calc R . . H7B H 0.4449 0.2978 -0.2647 0.048 Uiso 1 1 calc R . . C8 C 0.4258(3) 0.4756(3) -0.3059(3) 0.0436(8) Uani 1 1 d . . . H8A H 0.4714 0.5308 -0.3428 0.052 Uiso 1 1 calc R . . H8B H 0.3285 0.4668 -0.3507 0.052 Uiso 1 1 calc R . . C9 C 1.0000(3) 0.3174(3) 0.2245(2) 0.0301(7) Uani 1 1 d . . . H9 H 0.9351 0.2501 0.2208 0.036 Uiso 1 1 calc R . . C10 C 0.9879(4) 0.4035(3) 0.3086(3) 0.0430(8) Uani 1 1 d . . . H10A H 0.8907 0.4292 0.2919 0.052 Uiso 1 1 calc R . . H10B H 1.0445 0.4745 0.3076 0.052 Uiso 1 1 calc R . . C11 C 1.1460(4) 0.2689(4) 0.2530(3) 0.0479(9) Uani 1 1 d . . . H11A H 1.2096 0.3335 0.2487 0.057 Uiso 1 1 calc R . . H11B H 1.1499 0.2073 0.2005 0.057 Uiso 1 1 calc R . . C12 C 1.0358(4) 0.3479(4) 0.4208(3) 0.0491(9) Uani 1 1 d . . . H12A H 1.0313 0.4082 0.4743 0.059 Uiso 1 1 calc R . . H12B H 0.9730 0.2823 0.4242 0.059 Uiso 1 1 calc R . . C13 C 1.1931(4) 0.2157(4) 0.3654(3) 0.0527(10) Uani 1 1 d . . . H13A H 1.1368 0.1448 0.3670 0.063 Uiso 1 1 calc R . . H13B H 1.2904 0.1901 0.3827 0.063 Uiso 1 1 calc R . . C14 C 1.1807(3) 0.3014(3) 0.4478(3) 0.0445(9) Uani 1 1 d . . . H14A H 1.2450 0.3683 0.4522 0.053 Uiso 1 1 calc R . . H14B H 1.2065 0.2620 0.5184 0.053 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 0.0286(2) 0.0352(2) 0.0255(2) 0.00613(16) 0.00114(15) -0.00604(17) N1 0.0300(13) 0.0354(15) 0.0209(12) 0.0063(10) 0.0010(10) -0.0043(11) N2 0.0244(12) 0.0318(14) 0.0247(12) 0.0031(11) -0.0004(10) -0.0056(10) O1 0.0338(11) 0.0286(12) 0.0300(11) -0.0001(9) 0.0094(9) -0.0055(9) C1 0.0337(16) 0.0254(16) 0.0255(14) -0.0006(12) 0.0087(13) -0.0019(12) C2 0.0454(19) 0.0303(18) 0.0397(18) -0.0012(14) 0.0116(15) -0.0090(15) C3 0.0259(14) 0.0291(17) 0.0271(15) 0.0007(12) 0.0032(12) -0.0021(12) C4 0.0346(16) 0.0333(18) 0.0360(16) -0.0044(14) 0.0059(14) -0.0016(14) C5 0.0311(16) 0.0372(19) 0.0334(17) -0.0085(14) -0.0001(13) 0.0017(13) C6 0.0300(16) 0.0304(17) 0.053(2) 0.0035(16) 0.0073(15) 0.0046(14) C7 0.0296(16) 0.047(2) 0.0369(18) -0.0099(15) 0.0010(14) -0.0015(14) C8 0.0324(17) 0.050(2) 0.0368(18) 0.0067(16) -0.0055(14) -0.0011(16) C9 0.0316(16) 0.0310(17) 0.0246(15) 0.0038(12) 0.0042(13) -0.0067(13) C10 0.049(2) 0.048(2) 0.0311(17) 0.0051(15) 0.0112(15) 0.0163(17) C11 0.059(2) 0.055(2) 0.0331(18) 0.0131(16) 0.0196(17) 0.0265(18) C12 0.066(2) 0.056(2) 0.0270(17) -0.0007(16) 0.0168(17) 0.0135(19) C13 0.062(2) 0.063(3) 0.0339(19) 0.0212(17) 0.0155(17) 0.029(2) C14 0.0422(19) 0.055(2) 0.0276(17) 0.0112(16) -0.0011(15) -0.0062(17) _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 N1 1.873(2) . ? Cu1 N2 1.874(2) 3_765 ? Cu1 Cu1 2.4624(7) 3_765 ? N1 C1 1.321(4) . ? N1 C9 1.482(4) . ? N2 C1 1.331(4) . ? N2 C3 1.480(3) . ? N2 Cu1 1.874(2) 3_765 ? O1 C1 1.380(3) . ? O1 C2 1.432(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.524(4) . ? C3 C5 1.526(4) . ? C3 H3 1.0000 . ? C4 C6 1.519(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C7 1.527(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.508(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.521(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(5) . ? C9 C11 1.521(5) . ? C9 H9 1.0000 . ? C10 C12 1.538(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C13 1.530(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.505(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.489(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 175.83(10) . 3_765 ? N1 Cu1 Cu1 88.61(7) . 3_765 ? N2 Cu1 Cu1 87.27(7) 3_765 3_765 ? C1 N1 C9 119.8(2) . . ? C1 N1 Cu1 120.09(19) . . ? C9 N1 Cu1 119.90(18) . . ? C1 N2 C3 120.3(2) . . ? C1 N2 Cu1 121.23(19) . 3_765 ? C3 N2 Cu1 118.47(18) . 3_765 ? C1 O1 C2 112.9(2) . . ? N1 C1 N2 122.8(3) . . ? N1 C1 O1 118.6(2) . . ? N2 C1 O1 118.6(2) . . ? O1 C2 H2A 109.5 . . ? O1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? O1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 109.9(2) . . ? N2 C3 C5 109.7(2) . . ? C4 C3 C5 109.8(2) . . ? N2 C3 H3 109.1 . . ? C4 C3 H3 109.1 . . ? C5 C3 H3 109.1 . . ? C6 C4 C3 112.1(3) . . ? C6 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C6 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C3 C5 C7 111.1(3) . . ? C3 C5 H5A 109.4 . . ? C7 C5 H5A 109.4 . . ? C3 C5 H5B 109.4 . . ? C7 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C8 C6 C4 112.1(3) . . ? C8 C6 H6A 109.2 . . ? C4 C6 H6A 109.2 . . ? C8 C6 H6B 109.2 . . ? C4 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C5 110.7(3) . . ? C8 C7 H7A 109.5 . . ? C5 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C6 C8 C7 111.5(3) . . ? C6 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C6 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C10 110.2(3) . . ? N1 C9 C11 109.9(2) . . ? C10 C9 C11 110.5(3) . . ? N1 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C11 C9 H9 108.8 . . ? C9 C10 C12 111.6(3) . . ? C9 C10 H10A 109.3 . . ? C12 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C12 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C9 C11 C13 111.7(3) . . ? C9 C11 H11A 109.3 . . ? C13 C11 H11A 109.3 . . ? C9 C11 H11B 109.3 . . ? C13 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C14 C12 C10 111.4(3) . . ? C14 C12 H12A 109.4 . . ? C10 C12 H12A 109.4 . . ? C14 C12 H12B 109.4 . . ? C10 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C11 112.1(3) . . ? C14 C13 H13A 109.2 . . ? C11 C13 H13A 109.2 . . ? C14 C13 H13B 109.2 . . ? C11 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C12 110.8(3) . . ? C13 C14 H14A 109.5 . . ? C12 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.398 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.073 #===End