# Electronic Supplementary Material (ESI) for CrystEngComm # 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_lj-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C78 H84 Cu3 N12 O24' _chemical_formula_weight 1764.19 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.1047(18) _cell_length_b 26.696(3) _cell_length_c 18.618(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.839(2) _cell_angle_gamma 90.00 _cell_volume 8099.2(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.52 _cell_measurement_theta_max 26.26 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3660 _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22733 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.26 _reflns_number_total 8137 _reflns_number_gt 5711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0632P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8137 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _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 0.89086(2) 0.043771(13) 0.367346(19) 0.03028(11) Uani 1 1 d . . . O1 O 0.82934(12) 0.10256(8) 0.37094(12) 0.0393(5) Uani 1 1 d . . . O1W O 0.91571(13) 0.02671(9) 0.49646(12) 0.0501(6) Uani 1 1 d . . . N1 N 0.79026(14) -0.00096(9) 0.32363(14) 0.0355(6) Uani 1 1 d . . . C1 C 0.80691(16) 0.13502(11) 0.31467(17) 0.0339(7) Uani 1 1 d . . . Cu2 Cu 0.5000 0.10279(2) 0.2500 0.04211(16) Uani 1 2 d S . . O2 O 0.81407(14) 0.13062(9) 0.25221(13) 0.0479(6) Uani 1 1 d . . . C2 C 0.77742(17) 0.18369(11) 0.33479(17) 0.0351(7) Uani 1 1 d . A . N2 N 0.45639(17) 0.05192(11) 0.16239(18) 0.0506(7) Uani 1 1 d . . . O2W O 0.8225(2) 0.0374(2) 0.5790(2) 0.159(2) Uani 1 1 d . . . O3 O 0.57492(13) 0.15424(8) 0.31672(14) 0.0506(6) Uani 1 1 d . . . N3 N 0.41811(16) -0.10285(10) -0.00627(15) 0.0447(7) Uani 1 1 d . . . H3B H 0.4570 -0.1066 0.0410 0.054 Uiso 1 1 calc R . . C3 C 0.8342(2) 0.22228(13) 0.3653(2) 0.0590(10) Uani 1 1 d . . . H3A H 0.8875 0.2175 0.3714 0.071 Uiso 1 1 calc R . . O3W O 0.8280(6) 0.1342(3) 0.5164(3) 0.321(6) Uani 1 1 d . . . O4 O 0.63888(12) 0.11719(8) 0.25414(12) 0.0414(5) Uani 1 1 d . . . N4 N 0.26383(14) -0.16090(9) -0.07346(14) 0.0375(6) Uani 1 1 d . . . H4B H 0.2339 -0.1522 -0.1221 0.045 Uiso 1 1 calc R . . C4 C 0.8127(3) 0.26760(15) 0.3867(3) 0.0833(14) Uani 1 1 d . . . H4A H 0.8514 0.2931 0.4066 0.100 Uiso 1 1 calc R . . O5 O 0.95071(11) -0.01775(7) 0.35866(11) 0.0331(4) Uani 1 1 d . . . N5 N -0.00337(14) -0.08444(9) -0.09862(14) 0.0334(5) Uani 1 1 d . . . C5 C 0.7345(3) 0.27522(15) 0.3787(3) 0.0895(15) Uani 1 1 d . . . H5A H 0.7197 0.3061 0.3916 0.107 Uiso 1 1 calc R . . O6 O 0.90720(12) 0.00350(8) 0.23189(11) 0.0403(5) Uani 1 1 d . . . N6 N 0.58971(16) -0.14563(10) 0.26920(16) 0.0495(7) Uani 1 1 d . . . H6B H 0.6122 -0.1397 0.3197 0.059 Uiso 1 1 calc R . . C6 C 0.6783(2) 0.23676(13) 0.3514(2) 0.0633(11) Uani 1 1 d . A . H6A H 0.6258 0.2416 0.3476 0.076 Uiso 1 1 calc R . . C7 C 0.69849(18) 0.19092(11) 0.32942(18) 0.0373(7) Uani 1 1 d . . . O7 O 0.56796(17) -0.11672(10) 0.14808(15) 0.0795(9) Uani 1 1 d . . . C8 C 0.63440(18) 0.15095(11) 0.29733(17) 0.0363(7) Uani 1 1 d . A . O8 O 0.31757(18) -0.05060(9) -0.08629(14) 0.0730(8) Uani 1 1 d . . . O9 O 0.27085(13) -0.16590(9) 0.05030(12) 0.0499(6) Uani 1 1 d . . . C9 C 0.94331(16) -0.02575(11) 0.28810(16) 0.0299(6) Uani 1 1 d . . . C10 C 0.97664(18) -0.07354(11) 0.27203(16) 0.0345(7) Uani 1 1 d . . . C11 C 0.9556(3) -0.11867(12) 0.2943(2) 0.0573(10) Uani 1 1 d . . . H11A H 0.9266 -0.1189 0.3250 0.069 Uiso 1 1 calc R . . C12 C 0.9774(3) -0.16383(14) 0.2714(3) 0.0817(14) Uani 1 1 d . . . H12A H 0.9612 -0.1940 0.2852 0.098 Uiso 1 1 calc R . . C13 C 0.7412(2) -0.00246(15) 0.2482(2) 0.0661(12) Uani 1 1 d . . . H13A H 0.7453 0.0226 0.2155 0.079 Uiso 1 1 calc R . . C14 C 0.6830(2) -0.03931(16) 0.2138(2) 0.0711(13) Uani 1 1 d . . . H14A H 0.6518 -0.0397 0.1587 0.085 Uiso 1 1 calc R . . C15 C 0.67087(18) -0.07514(12) 0.25956(18) 0.0401(7) Uani 1 1 d . . . C16 C 0.7242(3) -0.07379(17) 0.3381(2) 0.0904(17) Uani 1 1 d . . . H16A H 0.7213 -0.0982 0.3724 0.108 Uiso 1 1 calc R . . C17 C 0.7820(3) -0.03697(16) 0.3673(2) 0.0835(15) Uani 1 1 d . . . H17A H 0.8176 -0.0375 0.4214 0.100 Uiso 1 1 calc R . . C18 C 0.60485(19) -0.11453(12) 0.2207(2) 0.0472(8) Uani 1 1 d . . . C19 C 0.53602(19) -0.18930(11) 0.2390(2) 0.0446(8) Uani 1 1 d . . . H19A H 0.5138 -0.1894 0.1807 0.053 Uiso 1 1 calc R . . C20 C 0.5874(2) -0.23698(13) 0.2706(2) 0.0588(10) Uani 1 1 d . . . H20A H 0.6318 -0.2372 0.2546 0.071 Uiso 1 1 calc R . . H20B H 0.6114 -0.2372 0.3284 0.071 Uiso 1 1 calc R . . C21 C 0.5349(2) -0.28352(13) 0.2383(3) 0.0666(11) Uani 1 1 d . . . H21A H 0.5132 -0.2843 0.1806 0.080 Uiso 1 1 calc R . . H21B H 0.5683 -0.3132 0.2594 0.080 Uiso 1 1 calc R . . C22 C 0.3763(3) 0.0440(2) 0.1135(4) 0.087(2) Uani 0.787(3) 1 d P A 1 H22A H 0.3368 0.0626 0.1212 0.105 Uiso 0.787(3) 1 calc PR A 1 C22' C 0.4172(13) 0.0574(10) 0.0995(16) 0.087(2) Uani 0.213(3) 1 d P A 2 H22B H 0.3930 0.0889 0.0859 0.105 Uiso 0.213(3) 1 calc PR A 2 C23 C 0.3517(3) 0.0100(2) 0.0538(4) 0.101(3) Uani 0.787(3) 1 d P A 1 H23A H 0.2962 0.0076 0.0193 0.121 Uiso 0.787(3) 1 calc PR A 1 C23' C 0.3966(13) 0.0229(11) 0.0331(15) 0.101(3) Uani 0.213(3) 1 d P A 2 H23B H 0.3755 0.0357 -0.0185 0.121 Uiso 0.213(3) 1 calc PR A 2 C24 C 0.4059(2) -0.02107(13) 0.04228(19) 0.0469(8) Uani 1 1 d . . . C25 C 0.4860(3) -0.00896(18) 0.0853(3) 0.0656(14) Uani 0.787(3) 1 d P A 1 H25A H 0.5260 -0.0256 0.0758 0.079 Uiso 0.787(3) 1 calc PR A 1 C25' C 0.4408(10) -0.0399(7) 0.1257(12) 0.0656(14) Uani 0.213(3) 1 d P A 2 H25B H 0.4462 -0.0740 0.1377 0.079 Uiso 0.213(3) 1 calc PR A 2 C26 C 0.5092(3) 0.02823(18) 0.1438(3) 0.0634(13) Uani 0.787(3) 1 d P A 1 H26A H 0.5645 0.0366 0.1708 0.076 Uiso 0.787(3) 1 calc PR A 1 C26' C 0.4647(10) -0.0032(7) 0.1845(12) 0.0634(13) Uani 0.213(3) 1 d P A 2 H26B H 0.4860 -0.0126 0.2379 0.076 Uiso 0.213(3) 1 calc PR A 2 C27 C 0.3770(2) -0.05976(13) -0.02275(19) 0.0479(8) Uani 1 1 d . A . C28 C 0.40215(18) -0.14456(11) -0.06263(18) 0.0393(7) Uani 1 1 d . . . H28A H 0.3770 -0.1313 -0.1172 0.047 Uiso 1 1 calc R . . C29 C 0.4842(2) -0.16887(14) -0.0470(2) 0.0546(9) Uani 1 1 d . . . H29A H 0.5179 -0.1447 -0.0581 0.065 Uiso 1 1 calc R . . H29B H 0.5126 -0.1779 0.0089 0.065 Uiso 1 1 calc R . . C30 C 0.4747(2) -0.21497(13) -0.0972(2) 0.0551(9) Uani 1 1 d . . . H30A H 0.4528 -0.2055 -0.1529 0.066 Uiso 1 1 calc R . . H30B H 0.5280 -0.2302 -0.0821 0.066 Uiso 1 1 calc R . . C31 C 0.4181(2) -0.25246(13) -0.0864(2) 0.0550(9) Uani 1 1 d . . . H31A H 0.4424 -0.2645 -0.0318 0.066 Uiso 1 1 calc R . . H31B H 0.4107 -0.2809 -0.1213 0.066 Uiso 1 1 calc R . . C32 C 0.3344(2) -0.22861(12) -0.1058(2) 0.0484(8) Uani 1 1 d . . . H32A H 0.3083 -0.2188 -0.1616 0.058 Uiso 1 1 calc R . . H32B H 0.2994 -0.2529 -0.0971 0.058 Uiso 1 1 calc R . . C33 C 0.34430(17) -0.18290(11) -0.05373(17) 0.0370(7) Uani 1 1 d . . . H33A H 0.3679 -0.1938 0.0021 0.044 Uiso 1 1 calc R . . C34 C 0.23462(18) -0.15376(11) -0.02016(17) 0.0356(7) Uani 1 1 d . . . C35 C 0.15038(17) -0.12980(10) -0.05057(16) 0.0325(6) Uani 1 1 d . . . C36 C 0.1158(2) -0.10136(12) -0.11898(18) 0.0456(8) Uani 1 1 d . . . H36A H 0.1434 -0.0968 -0.1506 0.055 Uiso 1 1 calc R . . C37 C 0.0404(2) -0.07981(13) -0.14012(18) 0.0470(8) Uani 1 1 d . . . H37A H 0.0184 -0.0607 -0.1865 0.056 Uiso 1 1 calc R . . C38 C 0.02936(19) -0.11255(12) -0.03296(19) 0.0452(8) Uani 1 1 d . . . H38A H -0.0003 -0.1174 -0.0035 0.054 Uiso 1 1 calc R . . C39 C 0.10533(19) -0.13470(12) -0.00706(19) 0.0448(8) Uani 1 1 d . . . H39A H 0.1265 -0.1531 0.0401 0.054 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 0.02473(18) 0.0322(2) 0.0345(2) 0.00155(15) 0.01350(15) 0.00055(15) O1 0.0386(11) 0.0406(12) 0.0411(11) 0.0093(10) 0.0195(10) 0.0121(10) O1W 0.0429(13) 0.0683(15) 0.0342(11) 0.0074(11) 0.0121(10) -0.0006(12) N1 0.0307(13) 0.0369(14) 0.0382(14) 0.0062(11) 0.0143(11) -0.0010(11) C1 0.0216(14) 0.0400(17) 0.0401(17) -0.0009(14) 0.0134(13) -0.0027(13) Cu2 0.0301(3) 0.0417(3) 0.0540(3) 0.000 0.0179(3) 0.000 O2 0.0514(13) 0.0562(15) 0.0463(13) 0.0007(11) 0.0308(11) 0.0031(12) C2 0.0307(15) 0.0339(16) 0.0393(16) -0.0010(13) 0.0140(13) -0.0006(13) N2 0.0321(14) 0.0540(19) 0.0608(19) -0.0065(14) 0.0156(14) 0.0011(13) O2W 0.084(3) 0.312(6) 0.059(2) 0.007(3) 0.0111(18) 0.040(3) O3 0.0369(12) 0.0503(14) 0.0756(16) -0.0129(12) 0.0348(12) -0.0052(11) N3 0.0377(14) 0.0461(16) 0.0403(15) -0.0029(12) 0.0077(12) 0.0048(13) C3 0.0394(19) 0.051(2) 0.086(3) -0.011(2) 0.0274(19) -0.0065(17) O3W 0.609(15) 0.262(7) 0.143(4) 0.075(5) 0.211(7) 0.253(9) O4 0.0378(12) 0.0391(12) 0.0517(13) -0.0081(10) 0.0237(10) -0.0048(10) N4 0.0312(13) 0.0498(16) 0.0327(13) 0.0066(11) 0.0151(11) 0.0113(12) C4 0.062(3) 0.054(3) 0.135(4) -0.036(3) 0.044(3) -0.026(2) O5 0.0306(10) 0.0369(11) 0.0329(11) -0.0018(9) 0.0150(9) 0.0011(9) N5 0.0322(13) 0.0331(13) 0.0370(13) 0.0012(11) 0.0169(11) 0.0003(11) C5 0.078(3) 0.046(2) 0.152(4) -0.044(3) 0.058(3) -0.010(2) O6 0.0370(11) 0.0442(13) 0.0379(12) 0.0080(10) 0.0146(10) 0.0043(10) N6 0.0459(16) 0.0464(17) 0.0510(17) -0.0080(13) 0.0163(14) -0.0171(14) C6 0.051(2) 0.044(2) 0.103(3) -0.018(2) 0.041(2) 0.0007(18) C7 0.0315(15) 0.0314(16) 0.0491(18) -0.0026(13) 0.0178(14) -0.0003(13) O7 0.0774(19) 0.0710(18) 0.0461(15) 0.0100(13) -0.0138(14) -0.0271(16) C8 0.0294(15) 0.0380(18) 0.0393(16) 0.0054(14) 0.0130(13) 0.0029(14) O8 0.089(2) 0.0546(16) 0.0463(15) 0.0002(12) 0.0021(14) 0.0226(15) O9 0.0503(13) 0.0640(15) 0.0361(12) 0.0109(11) 0.0194(11) 0.0244(12) C9 0.0232(13) 0.0345(16) 0.0335(15) 0.0002(13) 0.0136(12) -0.0052(12) C10 0.0405(17) 0.0316(16) 0.0317(15) -0.0002(12) 0.0160(13) -0.0016(14) C11 0.093(3) 0.0379(19) 0.065(2) -0.0014(17) 0.057(2) -0.007(2) C12 0.148(4) 0.037(2) 0.102(3) 0.003(2) 0.093(3) -0.007(3) C13 0.048(2) 0.086(3) 0.044(2) 0.0265(19) 0.0016(17) -0.027(2) C14 0.054(2) 0.100(3) 0.0345(18) 0.016(2) -0.0032(16) -0.033(2) C15 0.0334(16) 0.0376(17) 0.0400(17) 0.0052(13) 0.0072(14) -0.0008(14) C16 0.095(3) 0.095(3) 0.048(2) 0.026(2) 0.000(2) -0.059(3) C17 0.090(3) 0.095(3) 0.0360(19) 0.013(2) 0.000(2) -0.057(3) C18 0.0343(17) 0.0422(19) 0.051(2) 0.0034(16) 0.0057(16) -0.0014(15) C19 0.0365(17) 0.0376(17) 0.054(2) -0.0058(15) 0.0149(15) -0.0060(15) C20 0.0339(17) 0.053(2) 0.088(3) -0.009(2) 0.0251(18) 0.0008(17) C21 0.054(2) 0.040(2) 0.113(3) 0.000(2) 0.043(2) 0.0045(19) C22 0.033(3) 0.094(4) 0.108(4) -0.048(3) 0.005(3) 0.019(3) C22' 0.033(3) 0.094(4) 0.108(4) -0.048(3) 0.005(3) 0.019(3) C23 0.038(3) 0.120(5) 0.100(4) -0.063(4) -0.012(3) 0.030(4) C23' 0.038(3) 0.120(5) 0.100(4) -0.063(4) -0.012(3) 0.030(4) C24 0.0437(19) 0.047(2) 0.0421(18) -0.0005(15) 0.0115(15) 0.0092(17) C25 0.047(3) 0.060(3) 0.098(4) -0.024(3) 0.039(3) -0.004(2) C25' 0.047(3) 0.060(3) 0.098(4) -0.024(3) 0.039(3) -0.004(2) C26 0.034(2) 0.063(3) 0.089(3) -0.022(3) 0.024(2) -0.005(2) C26' 0.034(2) 0.063(3) 0.089(3) -0.022(3) 0.024(2) -0.005(2) C27 0.049(2) 0.046(2) 0.0425(19) 0.0038(15) 0.0139(16) 0.0033(17) C28 0.0373(16) 0.0417(18) 0.0386(17) -0.0001(14) 0.0162(14) 0.0051(14) C29 0.0382(18) 0.062(2) 0.066(2) -0.0023(19) 0.0255(17) 0.0066(17) C30 0.051(2) 0.056(2) 0.071(2) 0.0058(19) 0.0382(19) 0.0160(18) C31 0.065(2) 0.042(2) 0.074(2) 0.0056(18) 0.046(2) 0.0132(18) C32 0.053(2) 0.0400(19) 0.060(2) 0.0000(16) 0.0321(18) -0.0006(16) C33 0.0310(15) 0.0451(18) 0.0358(16) 0.0073(13) 0.0154(13) 0.0119(14) C34 0.0357(16) 0.0341(17) 0.0374(17) 0.0012(13) 0.0164(14) 0.0061(14) C35 0.0348(15) 0.0293(16) 0.0355(16) 0.0011(12) 0.0174(13) 0.0044(13) C36 0.0511(19) 0.051(2) 0.0478(18) 0.0170(15) 0.0335(16) 0.0200(16) C37 0.0503(19) 0.057(2) 0.0414(18) 0.0180(16) 0.0270(16) 0.0217(17) C38 0.0421(18) 0.051(2) 0.0539(19) 0.0192(16) 0.0317(16) 0.0100(16) C39 0.0433(18) 0.052(2) 0.0443(18) 0.0186(15) 0.0241(15) 0.0116(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 symme try. 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 1.943(2) . ? Cu1 O5 2.0125(19) . ? Cu1 N1 2.028(2) . ? Cu1 N5 2.047(2) 6_656 ? Cu1 O1W 2.290(2) . ? O1 C1 1.282(3) . ? N1 C13 1.295(4) . ? N1 C17 1.309(4) . ? C1 O2 1.231(3) . ? C1 C2 1.513(4) . ? Cu2 O3 1.950(2) . ? Cu2 O3 1.950(2) 2_655 ? Cu2 N2 2.001(3) . ? Cu2 N2 2.002(3) 2_655 ? Cu2 C8 2.546(3) . ? Cu2 C8 2.546(3) 2_655 ? C2 C3 1.390(4) . ? C2 C7 1.402(4) . ? N2 C22' 1.08(3) . ? N2 C26 1.312(5) . ? N2 C22 1.351(6) . ? N2 C26' 1.519(19) . ? O3 C8 1.279(3) . ? N3 C27 1.331(4) . ? N3 C28 1.470(4) . ? C3 C4 1.381(5) . ? O4 C8 1.234(3) . ? N4 C34 1.326(3) . ? N4 C33 1.461(3) . ? C4 C5 1.372(6) . ? O5 C9 1.279(3) . ? N5 C37 1.332(4) . ? N5 C38 1.333(4) . ? N5 Cu1 2.047(2) 6_455 ? C5 C6 1.378(5) . ? O6 C9 1.239(3) . ? N6 C18 1.340(4) . ? N6 C19 1.464(4) . ? C6 C7 1.389(4) . ? C7 C8 1.496(4) . ? O7 C18 1.221(4) . ? O8 C27 1.228(4) . ? O9 C34 1.227(3) . ? C9 C10 1.496(4) . ? C10 C11 1.380(4) . ? C10 C10 1.412(6) 2_755 ? C11 C12 1.391(5) . ? C12 C12 1.371(7) 2_755 ? C13 C14 1.378(5) . ? C14 C15 1.361(4) . ? C15 C16 1.357(5) . ? C15 C18 1.518(4) . ? C16 C17 1.364(5) . ? C19 C19 1.527(6) 2_655 ? C19 C20 1.534(4) . ? C20 C21 1.520(5) . ? C21 C21 1.505(7) 2_655 ? C22 C23 1.353(7) . ? C22' C23' 1.45(3) . ? C23 C24 1.371(6) . ? C23' C24 1.19(3) . ? C24 C25 1.355(5) . ? C24 C25' 1.49(2) . ? C24 C27 1.501(5) . ? C25 C26 1.396(6) . ? C25' C26' 1.39(2) . ? C28 C33 1.524(4) . ? C28 C29 1.529(4) . ? C29 C30 1.509(5) . ? C30 C31 1.506(5) . ? C31 C32 1.534(4) . ? C32 C33 1.520(4) . ? C34 C35 1.518(4) . ? C35 C36 1.377(4) . ? C35 C39 1.384(4) . ? C36 C37 1.372(4) . ? C38 C39 1.377(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O5 177.44(8) . . ? O1 Cu1 N1 93.52(9) . . ? O5 Cu1 N1 84.72(9) . . ? O1 Cu1 N5 91.95(9) . 6_656 ? O5 Cu1 N5 89.65(8) . 6_656 ? N1 Cu1 N5 172.69(9) . 6_656 ? O1 Cu1 O1W 88.73(8) . . ? O5 Cu1 O1W 93.19(8) . . ? N1 Cu1 O1W 92.03(9) . . ? N5 Cu1 O1W 92.94(9) 6_656 . ? C1 O1 Cu1 120.02(18) . . ? C13 N1 C17 116.1(3) . . ? C13 N1 Cu1 121.7(2) . . ? C17 N1 Cu1 120.6(2) . . ? O2 C1 O1 125.6(3) . . ? O2 C1 C2 120.7(3) . . ? O1 C1 C2 113.5(2) . . ? O3 Cu2 O3 90.42(14) . 2_655 ? O3 Cu2 N2 156.22(10) . . ? O3 Cu2 N2 92.35(11) 2_655 . ? O3 Cu2 N2 92.35(11) . 2_655 ? O3 Cu2 N2 156.22(10) 2_655 2_655 ? N2 Cu2 N2 94.54(17) . 2_655 ? O3 Cu2 C8 29.43(9) . . ? O3 Cu2 C8 99.17(9) 2_655 . ? N2 Cu2 C8 127.07(10) . . ? N2 Cu2 C8 94.73(10) 2_655 . ? O3 Cu2 C8 99.17(9) . 2_655 ? O3 Cu2 C8 29.43(9) 2_655 2_655 ? N2 Cu2 C8 94.73(10) . 2_655 ? N2 Cu2 C8 127.07(10) 2_655 2_655 ? C8 Cu2 C8 119.34(13) . 2_655 ? C3 C2 C7 118.4(3) . . ? C3 C2 C1 117.4(3) . . ? C7 C2 C1 124.0(3) . . ? C22' N2 C26 89.4(12) . . ? C22' N2 C22 44.6(14) . . ? C26 N2 C22 116.1(4) . . ? C22' N2 C26' 111.4(16) . . ? C26 N2 C26' 66.8(7) . . ? C22 N2 C26' 89.0(7) . . ? C22' N2 Cu2 129.1(13) . . ? C26 N2 Cu2 117.9(3) . . ? C22 N2 Cu2 125.5(3) . . ? C26' N2 Cu2 118.7(7) . . ? C8 O3 Cu2 102.08(19) . . ? C27 N3 C28 125.0(3) . . ? C4 C3 C2 121.1(3) . . ? C34 N4 C33 123.3(2) . . ? C5 C4 C3 120.3(4) . . ? C9 O5 Cu1 113.56(17) . . ? C37 N5 C38 116.4(3) . . ? C37 N5 Cu1 119.0(2) . 6_455 ? C38 N5 Cu1 124.37(19) . 6_455 ? C4 C5 C6 119.4(4) . . ? C18 N6 C19 122.1(3) . . ? C5 C6 C7 121.2(3) . . ? C6 C7 C2 119.4(3) . . ? C6 C7 C8 119.2(3) . . ? C2 C7 C8 121.3(3) . . ? O4 C8 O3 122.5(3) . . ? O4 C8 C7 121.4(3) . . ? O3 C8 C7 116.1(3) . . ? O4 C8 Cu2 74.33(17) . . ? O3 C8 Cu2 48.49(14) . . ? C7 C8 Cu2 163.0(2) . . ? O6 C9 O5 122.9(3) . . ? O6 C9 C10 118.6(2) . . ? O5 C9 C10 118.5(2) . . ? C11 C10 C10 119.20(19) . 2_755 ? C11 C10 C9 119.7(3) . . ? C10 C10 C9 120.81(15) 2_755 . ? C10 C11 C12 120.8(3) . . ? C12 C12 C11 119.9(2) 2_755 . ? N1 C13 C14 123.4(3) . . ? C15 C14 C13 120.6(3) . . ? C16 C15 C14 115.0(3) . . ? C16 C15 C18 125.1(3) . . ? C14 C15 C18 119.8(3) . . ? C15 C16 C17 120.7(3) . . ? N1 C17 C16 123.9(3) . . ? O7 C18 N6 122.9(3) . . ? O7 C18 C15 119.9(3) . . ? N6 C18 C15 117.3(3) . . ? N6 C19 C19 113.5(2) . 2_655 ? N6 C19 C20 108.9(3) . . ? C19 C19 C20 110.1(2) 2_655 . ? C21 C20 C19 110.9(3) . . ? C21 C21 C20 110.2(3) 2_655 . ? N2 C22 C23 122.0(5) . . ? N2 C22' C23' 130(2) . . ? C22 C23 C24 122.3(4) . . ? C24 C23' C22' 122(3) . . ? C23' C24 C25 84.1(10) . . ? C23' C24 C23 50.1(14) . . ? C25 C24 C23 114.7(4) . . ? C23' C24 C25' 117.1(14) . . ? C25 C24 C25' 66.8(7) . . ? C23 C24 C25' 92.8(7) . . ? C23' C24 C27 125.9(12) . . ? C25 C24 C27 123.2(3) . . ? C23 C24 C27 121.4(3) . . ? C25' C24 C27 116.7(7) . . ? C24 C25 C26 120.8(4) . . ? C26' C25' C24 115.4(16) . . ? N2 C26 C25 122.8(4) . . ? C25' C26' N2 120.7(17) . . ? O8 C27 N3 124.1(3) . . ? O8 C27 C24 119.4(3) . . ? N3 C27 C24 116.4(3) . . ? N3 C28 C33 111.2(2) . . ? N3 C28 C29 108.3(3) . . ? C33 C28 C29 110.6(3) . . ? C30 C29 C28 112.9(3) . . ? C31 C30 C29 111.2(3) . . ? C30 C31 C32 110.6(3) . . ? C33 C32 C31 110.7(3) . . ? N4 C33 C32 109.6(3) . . ? N4 C33 C28 111.1(2) . . ? C32 C33 C28 111.4(2) . . ? O9 C34 N4 124.1(3) . . ? O9 C34 C35 119.5(2) . . ? N4 C34 C35 116.4(2) . . ? C36 C35 C39 116.6(3) . . ? C36 C35 C34 123.7(3) . . ? C39 C35 C34 119.7(2) . . ? C37 C36 C35 119.4(3) . . ? N5 C37 C36 124.3(3) . . ? N5 C38 C39 122.7(3) . . ? C38 C39 C35 120.5(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.26 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.496 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 905476' ####################################################################### # # 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_lj-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C90 H102 Cu3 N16 O28' _chemical_formula_weight 2046.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1362(13) _cell_length_b 16.167(2) _cell_length_c 16.570(2) _cell_angle_alpha 110.640(2) _cell_angle_beta 92.365(2) _cell_angle_gamma 102.114(2) _cell_volume 2464.7(5) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.39 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1065 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.897 _exptl_absorpt_process_details SADABS _exptl_special_details ; The ADPs for pyridyl N and C atoms may be caused by the overlarge thermal vibration of the terminal atoms of the molecule. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omegascans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13061 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8567 _reflns_number_gt 5729 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0624P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8567 _refine_ls_number_parameters 619 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.018 _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 0.0000 0.5000 0.5000 0.0285(2) Uani 1 2 d S . . O1W O 0.3940(6) 0.3331(4) 0.3621(3) 0.135(2) Uani 1 1 d . . . O1 O -0.3323(3) 0.04742(18) 0.02008(18) 0.0322(7) Uani 1 1 d . . . C1 C -0.2030(4) 0.1624(2) 0.1470(2) 0.0181(8) Uani 1 1 d . . . N1 N 0.1724(4) 0.1422(2) 0.6019(2) 0.0384(9) Uani 1 1 d . . . H1A H 0.0916 0.1457 0.6140 0.046 Uiso 1 1 calc R . . Cu2 Cu 0.36384(5) 0.08841(3) 0.07864(3) 0.02109(15) Uani 1 1 d . . . O2W O 0.5897(5) 0.2765(4) 0.4340(4) 0.137(2) Uani 1 1 d . . . O2 O -0.1745(3) 0.3694(2) 0.39608(18) 0.0372(7) Uani 1 1 d . . . C2 C -0.2010(4) 0.2365(2) 0.2220(2) 0.0214(9) Uani 1 1 d . . . H2A H -0.2823 0.2510 0.2389 0.026 Uiso 1 1 d R . . N2 N 0.2545(4) 0.0026(3) 0.4627(2) 0.0395(9) Uani 1 1 d . . . H2B H 0.3206 0.0492 0.4717 0.047 Uiso 1 1 calc R . . O3W O 0.6523(6) 0.3003(4) 0.6129(4) 0.153(2) Uani 1 1 d . . . O3 O 0.1697(2) 0.09493(18) 0.08391(17) 0.0261(6) Uani 1 1 d . . . C3 C -0.0817(4) 0.1383(3) 0.1234(2) 0.0219(9) Uani 1 1 d . . . H3A H -0.0829 0.0876 0.0739 0.026 Uiso 1 1 calc R . . N3 N 0.3791(3) 0.1484(2) -0.0117(2) 0.0271(8) Uani 1 1 d . . . O4W O 0.7727(9) 0.4683(5) 0.6926(5) 0.221(4) Uani 1 1 d U . . O4 O 0.2813(3) 0.21363(19) 0.1978(2) 0.0397(8) Uani 1 1 d . . . C4 C -0.0767(4) 0.3684(3) 0.3542(3) 0.0273(10) Uani 1 1 d . . . N4 N 0.3385(3) 0.0327(2) 0.1721(2) 0.0263(8) Uani 1 1 d . . . O5 O -0.4419(2) 0.13102(18) 0.12046(17) 0.0269(6) Uani 1 1 d . . . C5 C 0.0419(4) 0.1904(3) 0.1744(2) 0.0226(9) Uani 1 1 d . . . N5 N 0.0740(4) 0.4107(2) 0.5364(2) 0.0319(9) Uani 1 1 d . . . O6 O 0.1125(3) -0.1199(2) 0.3621(2) 0.0486(9) Uani 1 1 d . . . C6 C 0.1741(4) 0.1653(3) 0.1519(3) 0.0250(9) Uani 1 1 d . . . N6 N 0.4036(4) 0.3735(3) -0.1591(2) 0.0457(10) Uani 1 1 d . . . H27A H 0.3561 0.3844 -0.1164 0.055 Uiso 1 1 calc R . . O7 O 0.0330(3) 0.43274(18) 0.38035(17) 0.0307(7) Uani 1 1 d . . . C7 C 0.0418(4) 0.2664(3) 0.2469(3) 0.0276(10) Uani 1 1 d . . . H7A H 0.1242 0.3024 0.2795 0.033 Uiso 1 1 calc R . . N7 N 0.6724(4) 0.4830(3) -0.1376(3) 0.0567(12) Uani 1 1 d . . . H29A H 0.7131 0.4680 -0.1832 0.068 Uiso 1 1 calc R . . O8 O 0.3546(3) 0.1955(2) 0.5445(2) 0.0475(9) Uani 1 1 d . . . C8 C -0.3356(4) 0.1080(2) 0.0905(2) 0.0207(9) Uani 1 1 d . . . N8 N 1.0094(6) 0.3055(4) -0.0934(6) 0.108(2) Uani 1 1 d . . . O9 O 0.4979(4) 0.2666(2) -0.2486(2) 0.0599(10) Uani 1 1 d . . . C9 C 0.4340(5) 0.4421(3) -0.1989(3) 0.0431(12) Uani 1 1 d . . . H9A H 0.4619 0.4138 -0.2562 0.052 Uiso 1 1 calc R . . C10 C 0.2044(5) -0.0152(3) 0.5379(3) 0.0392(11) Uani 1 1 d . . . H10A H 0.1059 -0.0410 0.5244 0.047 Uiso 1 1 calc R . . O10 O 0.6818(4) 0.5021(3) 0.0020(2) 0.0803(13) Uani 1 1 d . . . C11 C -0.0777(4) 0.2902(3) 0.2722(2) 0.0230(9) Uani 1 1 d . . . C12 C 0.4159(4) 0.2435(3) -0.1238(3) 0.0329(10) Uani 1 1 d . . . C13 C 0.2305(5) 0.0724(3) 0.6174(3) 0.0397(12) Uani 1 1 d . . . H13A H 0.3290 0.0964 0.6327 0.048 Uiso 1 1 calc R . . C14 C 0.4006(4) 0.0790(3) 0.2531(3) 0.0343(11) Uani 1 1 d . . . H14A H 0.4726 0.1290 0.2628 0.041 Uiso 1 1 calc R . . C15 C 0.2578(4) -0.0199(3) 0.3094(3) 0.0321(10) Uani 1 1 d . . . C16 C 0.2030(5) -0.0494(3) 0.3811(3) 0.0374(11) Uani 1 1 d . . . C17 C 0.4434(5) 0.2953(3) -0.1836(3) 0.0401(12) Uani 1 1 d . . . C18 C 0.2371(4) -0.0406(3) 0.1598(3) 0.0344(11) Uani 1 1 d . . . H18A H 0.1925 -0.0740 0.1039 0.041 Uiso 1 1 calc R . . C19 C 0.3631(4) 0.0562(3) 0.3232(3) 0.0367(11) Uani 1 1 d . . . H19A H 0.4077 0.0913 0.3788 0.044 Uiso 1 1 calc R . . C20 C 0.5528(5) 0.5187(3) -0.1421(3) 0.0441(12) Uani 1 1 d . . . H20A H 0.5277 0.5422 -0.0832 0.053 Uiso 1 1 calc R . . C21 C 0.1964(5) -0.0682(3) 0.2255(3) 0.0393(11) Uani 1 1 d . . . H21A H 0.1266 -0.1201 0.2134 0.047 Uiso 1 1 calc R . . C22 C 0.1785(5) 0.2736(3) 0.5617(3) 0.0341(11) Uani 1 1 d . . . C23 C 0.2429(5) 0.2010(3) 0.5691(3) 0.0386(11) Uani 1 1 d . . . C24 C 0.5015(5) 0.1896(3) -0.1173(3) 0.0426(12) Uani 1 1 d . . . H24A H 0.5724 0.1835 -0.1512 0.051 Uiso 1 1 calc R . . C25 C 0.8245(5) 0.4144(4) -0.0803(4) 0.0566(15) Uani 1 1 d . . . C26 C 0.4814(5) 0.1450(3) -0.0607(3) 0.0400(12) Uani 1 1 d . . . H26A H 0.5418 0.1104 -0.0560 0.048 Uiso 1 1 calc R . . C27 C 0.2929(5) 0.1971(3) -0.0224(3) 0.0428(12) Uani 1 1 d . . . H27B H 0.2184 0.1983 0.0085 0.051 Uiso 1 1 calc R . . C28 C 0.3080(5) 0.2454(3) -0.0764(3) 0.0477(13) Uani 1 1 d . . . H28A H 0.2459 0.2791 -0.0807 0.057 Uiso 1 1 calc R . . C29 C 0.0467(5) 0.2797(3) 0.5739(3) 0.0467(13) Uani 1 1 d . . . H29B H -0.0099 0.2377 0.5915 0.056 Uiso 1 1 calc R . . C30 C 0.7222(5) 0.4724(4) -0.0682(4) 0.0521(14) Uani 1 1 d . . . C31 C 0.2568(5) 0.3408(3) 0.5389(4) 0.0569(15) Uani 1 1 d . . . H31A H 0.3474 0.3412 0.5313 0.068 Uiso 1 1 calc R . . C32 C 0.2017(5) 0.4067(3) 0.5273(4) 0.0540(14) Uani 1 1 d . . . H32A H 0.2572 0.4513 0.5122 0.065 Uiso 1 1 calc R . . C33 C 0.1722(6) 0.0523(3) 0.6939(3) 0.0531(14) Uani 1 1 d . . . H33A H 0.1897 0.1083 0.7446 0.064 Uiso 1 1 calc R . . H33B H 0.0744 0.0286 0.6799 0.064 Uiso 1 1 calc R . . C34 C 0.3085(5) 0.4747(3) -0.2109(3) 0.0501(14) Uani 1 1 d . . . H34A H 0.2699 0.4920 -0.1565 0.060 Uiso 1 1 calc R . . H34B H 0.2414 0.4252 -0.2540 0.060 Uiso 1 1 calc R . . C35 C 0.9751(9) 0.3305(6) -0.1555(7) 0.123(3) Uani 1 1 d . . . H35A H 1.0163 0.3115 -0.2058 0.147 Uiso 1 1 calc R . . C36 C 0.2699(6) -0.0836(3) 0.5581(3) 0.0569(15) Uani 1 1 d . . . H36A H 0.2519 -0.1398 0.5075 0.068 Uiso 1 1 calc R . . H36B H 0.3677 -0.0595 0.5710 0.068 Uiso 1 1 calc R . . C37 C -0.0014(5) 0.3477(3) 0.5604(3) 0.0471(13) Uani 1 1 d . . . H37A H -0.0912 0.3497 0.5683 0.057 Uiso 1 1 calc R . . C38 C 0.5819(6) 0.5967(3) -0.1748(4) 0.0636(16) Uani 1 1 d . . . H38A H 0.6112 0.5758 -0.2321 0.076 Uiso 1 1 calc R . . H38B H 0.6547 0.6456 -0.1360 0.076 Uiso 1 1 calc R . . C39 C 0.3386(6) 0.5559(4) -0.2400(4) 0.0684(18) Uani 1 1 d . . . H39A H 0.3633 0.5363 -0.2986 0.082 Uiso 1 1 calc R . . H39B H 0.2574 0.5785 -0.2409 0.082 Uiso 1 1 calc R . . C40 C 0.4537(6) 0.6321(4) -0.1795(4) 0.0694(18) Uani 1 1 d . . . H40A H 0.4266 0.6552 -0.1219 0.083 Uiso 1 1 calc R . . H40B H 0.4731 0.6816 -0.2007 0.083 Uiso 1 1 calc R . . C41 C 0.2349(7) -0.0165(4) 0.7146(4) 0.0675(17) Uani 1 1 d . . . H41A H 0.3314 0.0092 0.7338 0.081 Uiso 1 1 calc R . . H41B H 0.1931 -0.0304 0.7615 0.081 Uiso 1 1 calc R . . C42 C 0.9509(9) 0.3354(6) -0.0236(7) 0.131(3) Uani 1 1 d U . . H42A H 0.9710 0.3181 0.0224 0.157 Uiso 1 1 calc R . . C43 C 0.2145(7) -0.1032(4) 0.6352(4) 0.0696(18) Uani 1 1 d . . . H43A H 0.1183 -0.1324 0.6201 0.084 Uiso 1 1 calc R . . H43B H 0.2604 -0.1447 0.6484 0.084 Uiso 1 1 calc R . . C44 C 0.8614(8) 0.3907(5) -0.0133(5) 0.105(3) Uani 1 1 d . . . H44A H 0.8266 0.4118 0.0392 0.126 Uiso 1 1 calc R . . C45 C 0.8840(7) 0.3822(5) -0.1542(5) 0.097(2) Uani 1 1 d . . . H45A H 0.8627 0.3954 -0.2027 0.117 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 0.0398(5) 0.0190(4) 0.0219(4) 0.0014(3) 0.0037(3) 0.0078(3) O1W 0.128(5) 0.180(6) 0.073(4) 0.020(4) 0.010(3) 0.036(4) O1 0.0255(16) 0.0288(16) 0.0293(17) -0.0062(14) 0.0000(13) 0.0092(13) C1 0.0155(19) 0.017(2) 0.020(2) 0.0045(17) 0.0041(16) 0.0043(16) N1 0.042(2) 0.039(2) 0.047(2) 0.028(2) 0.0143(19) 0.0148(18) Cu2 0.0157(3) 0.0236(3) 0.0236(3) 0.0068(2) 0.00408(19) 0.0069(2) O2W 0.084(4) 0.171(6) 0.167(6) 0.086(5) 0.037(4) 0.010(4) O2 0.0324(17) 0.0389(18) 0.0308(17) 0.0007(15) 0.0105(14) 0.0085(14) C2 0.019(2) 0.024(2) 0.020(2) 0.0050(18) 0.0048(16) 0.0089(17) N2 0.048(2) 0.040(2) 0.038(2) 0.023(2) 0.0139(19) 0.0084(19) O3W 0.100(4) 0.173(6) 0.165(6) 0.058(5) 0.043(4) -0.007(4) O3 0.0182(14) 0.0306(16) 0.0273(16) 0.0051(14) 0.0048(12) 0.0105(12) C3 0.022(2) 0.021(2) 0.022(2) 0.0060(18) 0.0021(17) 0.0077(17) N3 0.0246(18) 0.0274(19) 0.031(2) 0.0095(17) 0.0033(15) 0.0113(16) O4W 0.233(7) 0.187(6) 0.192(6) 0.023(5) 0.129(5) 0.007(5) O4 0.0172(16) 0.0337(17) 0.054(2) -0.0008(16) -0.0006(14) 0.0064(14) C4 0.031(2) 0.024(2) 0.026(2) 0.0042(19) 0.003(2) 0.013(2) N4 0.0230(18) 0.0249(19) 0.031(2) 0.0099(16) 0.0065(15) 0.0068(15) O5 0.0126(14) 0.0348(16) 0.0292(16) 0.0067(13) 0.0043(12) 0.0057(12) C5 0.015(2) 0.026(2) 0.027(2) 0.0083(19) 0.0036(17) 0.0064(17) N5 0.042(2) 0.026(2) 0.024(2) 0.0052(17) 0.0039(17) 0.0093(17) O6 0.054(2) 0.045(2) 0.050(2) 0.0258(18) 0.0161(17) 0.0004(18) C6 0.019(2) 0.026(2) 0.033(2) 0.011(2) 0.0065(19) 0.0082(18) N6 0.070(3) 0.044(2) 0.041(2) 0.027(2) 0.022(2) 0.028(2) O7 0.0339(17) 0.0238(15) 0.0254(16) -0.0004(13) 0.0049(13) 0.0043(14) C7 0.024(2) 0.026(2) 0.025(2) 0.0014(19) -0.0041(18) 0.0036(18) N7 0.061(3) 0.073(3) 0.054(3) 0.030(3) 0.021(2) 0.039(3) O8 0.040(2) 0.050(2) 0.067(2) 0.0357(19) 0.0137(17) 0.0149(17) C8 0.020(2) 0.020(2) 0.023(2) 0.0102(19) 0.0012(17) 0.0024(17) N8 0.065(4) 0.095(5) 0.167(8) 0.036(5) 0.007(4) 0.050(4) O9 0.102(3) 0.053(2) 0.042(2) 0.0270(19) 0.031(2) 0.034(2) C9 0.070(4) 0.036(3) 0.033(3) 0.020(2) 0.010(2) 0.019(3) C10 0.052(3) 0.039(3) 0.036(3) 0.024(2) 0.010(2) 0.012(2) O10 0.101(3) 0.116(4) 0.042(2) 0.020(2) 0.014(2) 0.078(3) C11 0.020(2) 0.023(2) 0.021(2) 0.0021(18) -0.0025(17) 0.0058(17) C12 0.042(3) 0.028(2) 0.031(2) 0.009(2) 0.007(2) 0.015(2) C13 0.047(3) 0.042(3) 0.039(3) 0.025(2) 0.006(2) 0.012(2) C14 0.028(2) 0.040(3) 0.035(3) 0.017(2) 0.003(2) 0.002(2) C15 0.036(3) 0.032(2) 0.033(3) 0.017(2) 0.010(2) 0.009(2) C16 0.040(3) 0.041(3) 0.043(3) 0.025(3) 0.010(2) 0.015(2) C17 0.056(3) 0.038(3) 0.033(3) 0.018(2) 0.008(2) 0.018(2) C18 0.037(3) 0.032(3) 0.029(2) 0.010(2) 0.006(2) 0.000(2) C19 0.033(3) 0.048(3) 0.026(2) 0.016(2) -0.002(2) 0.000(2) C20 0.052(3) 0.049(3) 0.040(3) 0.020(3) 0.009(2) 0.021(3) C21 0.043(3) 0.030(3) 0.040(3) 0.012(2) 0.012(2) -0.002(2) C22 0.043(3) 0.029(2) 0.029(2) 0.011(2) 0.004(2) 0.007(2) C23 0.047(3) 0.033(3) 0.035(3) 0.014(2) 0.002(2) 0.008(2) C24 0.050(3) 0.051(3) 0.042(3) 0.026(3) 0.025(2) 0.027(3) C25 0.047(3) 0.049(3) 0.070(4) 0.017(3) 0.001(3) 0.015(3) C26 0.042(3) 0.050(3) 0.043(3) 0.024(3) 0.015(2) 0.028(2) C27 0.037(3) 0.058(3) 0.053(3) 0.033(3) 0.019(2) 0.028(2) C28 0.048(3) 0.059(3) 0.062(3) 0.040(3) 0.019(3) 0.033(3) C29 0.054(3) 0.040(3) 0.061(3) 0.034(3) 0.019(3) 0.015(2) C30 0.049(3) 0.055(3) 0.059(4) 0.023(3) 0.005(3) 0.023(3) C31 0.045(3) 0.055(3) 0.090(4) 0.046(3) 0.017(3) 0.016(3) C32 0.043(3) 0.049(3) 0.086(4) 0.045(3) 0.016(3) 0.009(3) C33 0.078(4) 0.052(3) 0.041(3) 0.029(3) 0.015(3) 0.020(3) C34 0.062(3) 0.044(3) 0.048(3) 0.024(3) -0.007(3) 0.011(3) C35 0.115(7) 0.138(8) 0.161(9) 0.068(7) 0.075(6) 0.091(6) C36 0.082(4) 0.048(3) 0.054(3) 0.030(3) 0.012(3) 0.023(3) C37 0.044(3) 0.049(3) 0.064(4) 0.034(3) 0.021(3) 0.018(3) C38 0.069(4) 0.048(3) 0.074(4) 0.026(3) -0.001(3) 0.011(3) C39 0.082(4) 0.063(4) 0.079(4) 0.049(4) -0.007(4) 0.019(3) C40 0.076(4) 0.045(3) 0.099(5) 0.042(4) -0.001(4) 0.016(3) C41 0.103(5) 0.074(4) 0.050(4) 0.043(3) 0.012(3) 0.034(4) C42 0.132(6) 0.140(6) 0.139(7) 0.043(5) -0.013(5) 0.090(6) C43 0.114(5) 0.059(4) 0.063(4) 0.046(3) 0.020(4) 0.037(4) C44 0.117(6) 0.134(7) 0.084(5) 0.030(5) 0.001(4) 0.092(5) C45 0.105(6) 0.114(6) 0.114(6) 0.059(5) 0.058(5) 0.073(5) _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 invol ving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O7 1.978(3) . ? Cu1 O7 1.978(3) 2_566 ? Cu1 N5 2.011(3) . ? Cu1 N5 2.011(3) 2_566 ? Cu1 C4 2.549(4) 2_566 ? Cu1 C4 2.549(4) . ? O1 C8 1.239(4) . ? O1 Cu2 2.175(3) 2 ? C1 C2 1.385(5) . ? C1 C3 1.397(5) . ? C1 C8 1.509(5) . ? N1 C23 1.348(5) . ? N1 C13 1.469(5) . ? Cu2 O5 1.953(2) 1_655 ? Cu2 O3 1.996(2) . ? Cu2 N3 2.047(3) . ? Cu2 N4 2.049(3) . ? Cu2 O1 2.175(3) 2 ? O2 C4 1.233(5) . ? C2 C11 1.399(5) . ? N2 C16 1.327(6) . ? N2 C10 1.463(5) . ? O3 C6 1.280(5) . ? C3 C5 1.400(5) . ? N3 C27 1.337(5) . ? N3 C26 1.341(5) . ? O4 C6 1.235(4) . ? C4 O7 1.289(5) . ? C4 C11 1.492(5) . ? N4 C14 1.335(5) . ? N4 C18 1.343(5) . ? O5 C8 1.276(4) . ? O5 Cu2 1.953(2) 1_455 ? C5 C7 1.383(5) . ? C5 C6 1.504(5) . ? N5 C32 1.322(6) . ? N5 C37 1.327(5) . ? O6 C16 1.234(5) . ? N6 C17 1.339(6) . ? N6 C9 1.466(5) . ? C7 C11 1.384(5) . ? N7 C30 1.317(6) . ? N7 C20 1.458(6) . ? O8 C23 1.230(5) . ? N8 C35 1.291(10) . ? N8 C42 1.306(10) . ? O9 C17 1.219(5) . ? C9 C34 1.507(6) . ? C9 C20 1.526(6) . ? C10 C13 1.519(6) . ? C10 C36 1.525(6) . ? O10 C30 1.216(6) . ? C12 C28 1.371(6) . ? C12 C24 1.379(6) . ? C12 C17 1.506(6) . ? C13 C33 1.528(6) . ? C14 C19 1.380(6) . ? C15 C21 1.375(6) . ? C15 C19 1.392(6) . ? C15 C16 1.514(6) . ? C18 C21 1.362(6) . ? C20 C38 1.519(6) . ? C22 C29 1.379(6) . ? C22 C31 1.381(6) . ? C22 C23 1.495(6) . ? C24 C26 1.368(6) . ? C25 C44 1.357(8) . ? C25 C45 1.370(8) . ? C25 C30 1.512(7) . ? C27 C28 1.374(6) . ? C29 C37 1.374(6) . ? C31 C32 1.367(6) . ? C33 C41 1.519(7) . ? C34 C39 1.529(6) . ? C35 C45 1.365(9) . ? C36 C43 1.522(7) . ? C38 C40 1.535(7) . ? C39 C40 1.521(7) . ? C41 C43 1.515(7) . ? C42 C44 1.377(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cu1 O7 179.999(1) . 2_566 ? O7 Cu1 N5 87.52(12) . . ? O7 Cu1 N5 92.48(12) 2_566 . ? O7 Cu1 N5 92.48(12) . 2_566 ? O7 Cu1 N5 87.52(12) 2_566 2_566 ? N5 Cu1 N5 179.999(1) . 2_566 ? O7 Cu1 C4 150.17(12) . 2_566 ? O7 Cu1 C4 29.83(12) 2_566 2_566 ? N5 Cu1 C4 94.99(12) . 2_566 ? N5 Cu1 C4 85.01(13) 2_566 2_566 ? O7 Cu1 C4 29.83(12) . . ? O7 Cu1 C4 150.17(12) 2_566 . ? N5 Cu1 C4 85.01(12) . . ? N5 Cu1 C4 94.99(13) 2_566 . ? C4 Cu1 C4 179.999(1) 2_566 . ? C8 O1 Cu2 159.2(3) . 2 ? C2 C1 C3 119.9(3) . . ? C2 C1 C8 120.2(3) . . ? C3 C1 C8 119.9(3) . . ? C23 N1 C13 121.5(4) . . ? O5 Cu2 O3 153.81(11) 1_655 . ? O5 Cu2 N3 93.50(12) 1_655 . ? O3 Cu2 N3 90.45(12) . . ? O5 Cu2 N4 88.83(12) 1_655 . ? O3 Cu2 N4 86.13(12) . . ? N3 Cu2 N4 176.17(13) . . ? O5 Cu2 O1 107.08(11) 1_655 2 ? O3 Cu2 O1 98.58(10) . 2 ? N3 Cu2 O1 92.62(12) . 2 ? N4 Cu2 O1 89.59(12) . 2 ? C1 C2 C11 120.5(4) . . ? C16 N2 C10 123.3(4) . . ? C6 O3 Cu2 103.9(2) . . ? C1 C3 C5 119.9(4) . . ? C27 N3 C26 116.1(4) . . ? C27 N3 Cu2 122.5(3) . . ? C26 N3 Cu2 121.4(3) . . ? O2 C4 O7 122.0(4) . . ? O2 C4 C11 121.2(4) . . ? O7 C4 C11 116.7(4) . . ? O2 C4 Cu1 72.9(2) . . ? O7 C4 Cu1 49.75(19) . . ? C11 C4 Cu1 162.6(3) . . ? C14 N4 C18 116.9(4) . . ? C14 N4 Cu2 120.6(3) . . ? C18 N4 Cu2 120.7(3) . . ? C8 O5 Cu2 134.3(2) . 1_455 ? C7 C5 C3 119.1(4) . . ? C7 C5 C6 119.6(3) . . ? C3 C5 C6 121.3(3) . . ? C32 N5 C37 116.8(4) . . ? C32 N5 Cu1 118.9(3) . . ? C37 N5 Cu1 123.9(3) . . ? O4 C6 O3 123.0(4) . . ? O4 C6 C5 119.5(4) . . ? O3 C6 C5 117.5(3) . . ? C17 N6 C9 125.6(4) . . ? C4 O7 Cu1 100.4(2) . . ? C5 C7 C11 121.7(3) . . ? C30 N7 C20 124.3(4) . . ? O1 C8 O5 126.1(3) . . ? O1 C8 C1 118.4(3) . . ? O5 C8 C1 115.4(3) . . ? C35 N8 C42 114.5(7) . . ? N6 C9 C34 109.9(4) . . ? N6 C9 C20 108.4(4) . . ? C34 C9 C20 113.0(4) . . ? N2 C10 C13 110.9(4) . . ? N2 C10 C36 111.4(4) . . ? C13 C10 C36 109.7(4) . . ? C7 C11 C2 118.8(4) . . ? C7 C11 C4 120.9(3) . . ? C2 C11 C4 120.2(4) . . ? C28 C12 C24 117.8(4) . . ? C28 C12 C17 123.6(4) . . ? C24 C12 C17 118.7(4) . . ? N1 C13 C10 112.6(3) . . ? N1 C13 C33 109.6(4) . . ? C10 C13 C33 109.7(4) . . ? N4 C14 C19 123.3(4) . . ? C21 C15 C19 117.2(4) . . ? C21 C15 C16 118.6(4) . . ? C19 C15 C16 124.1(4) . . ? O6 C16 N2 122.6(4) . . ? O6 C16 C15 119.4(4) . . ? N2 C16 C15 118.0(4) . . ? O9 C17 N6 124.0(4) . . ? O9 C17 C12 121.3(4) . . ? N6 C17 C12 114.7(4) . . ? N4 C18 C21 123.1(4) . . ? C14 C19 C15 119.1(4) . . ? N7 C20 C38 111.5(4) . . ? N7 C20 C9 109.8(4) . . ? C38 C20 C9 111.4(4) . . ? C18 C21 C15 120.4(4) . . ? C29 C22 C31 116.0(4) . . ? C29 C22 C23 126.5(4) . . ? C31 C22 C23 117.5(4) . . ? O8 C23 N1 122.5(4) . . ? O8 C23 C22 120.2(4) . . ? N1 C23 C22 117.3(4) . . ? C26 C24 C12 119.5(4) . . ? C44 C25 C45 116.0(6) . . ? C44 C25 C30 118.4(6) . . ? C45 C25 C30 125.6(6) . . ? N3 C26 C24 123.5(4) . . ? N3 C27 C28 123.8(4) . . ? C12 C28 C27 119.2(4) . . ? C37 C29 C22 120.3(4) . . ? O10 C30 N7 122.2(5) . . ? O10 C30 C25 120.3(5) . . ? N7 C30 C25 117.3(5) . . ? C32 C31 C22 120.2(5) . . ? N5 C32 C31 123.6(5) . . ? C41 C33 C13 111.2(4) . . ? C9 C34 C39 112.3(4) . . ? N8 C35 C45 126.0(8) . . ? C43 C36 C10 110.8(4) . . ? N5 C37 C29 123.1(5) . . ? C20 C38 C40 110.2(5) . . ? C40 C39 C34 111.3(4) . . ? C39 C40 C38 110.1(5) . . ? C43 C41 C33 110.4(4) . . ? N8 C42 C44 124.8(8) . . ? C41 C43 C36 111.3(4) . . ? C25 C44 C42 119.6(8) . . ? C35 C45 C25 119.1(7) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.772 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.080 #==End _database_code_depnum_ccdc_archive 'CCDC 905477' ####################################################################### # # 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_lj-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cu N4 O7' _chemical_formula_weight 570.05 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9622(10) _cell_length_b 18.3107(18) _cell_length_c 15.7167(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.788(2) _cell_angle_gamma 90.00 _cell_volume 2744.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.776 _exptl_absorpt_correction_T_max 0.845 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14191 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4834 _reflns_number_gt 4157 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0747P)^2^+0.8707P] 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 4834 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1156 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.56114(3) 0.027633(15) 0.268714(18) 0.02515(13) Uani 1 1 d . . . N1 N 0.5151(2) 0.08606(11) 0.15288(13) 0.0305(5) Uani 1 1 d . . . O1 O 0.3480(3) 0.28162(12) -0.07216(14) 0.0617(7) Uani 1 1 d . . . O1W O 0.6104(2) 0.13653(11) 0.34122(14) 0.0482(5) Uani 1 1 d . . . H1WA H 0.5959 0.1591 0.3850 0.058 Uiso 1 1 d R . . H1WB H 0.6661 0.1623 0.3217 0.058 Uiso 1 1 d R . . N2 N 0.4610(2) 0.21077(11) -0.14636(13) 0.0308(5) Uani 1 1 d . . . H2A H 0.5116 0.1723 -0.1441 0.037 Uiso 1 1 calc R . . O2 O 0.85125(18) 0.30899(10) -0.14808(13) 0.0409(5) Uani 1 1 d . . . O3 O 0.72280(17) -0.01665(9) 0.24360(12) 0.0318(4) Uani 1 1 d . . . N3 N 0.6243(2) 0.33845(11) -0.16505(13) 0.0304(5) Uani 1 1 d . . . H3A H 0.5684 0.3646 -0.1450 0.036 Uiso 1 1 calc R . . O4 O 0.90055(18) 0.05582(10) 0.31391(13) 0.0376(4) Uani 1 1 d . . . N4 N 0.8919(2) 0.47905(10) 0.10897(13) 0.0277(5) Uani 1 1 d . . . O5 O 1.39603(18) -0.07852(10) 0.18072(13) 0.0390(4) Uani 1 1 d . . . O6 O 1.35719(16) 0.01891(9) 0.25452(11) 0.0272(4) Uani 1 1 d . . . C9 C 0.8512(2) 0.00379(13) 0.26475(16) 0.0259(5) Uani 1 1 d . . . C10 C 0.7620(2) 0.34513(12) -0.12626(15) 0.0265(5) Uani 1 1 d . . . C12 C 0.4289(3) 0.25560(13) -0.22675(16) 0.0280(5) Uani 1 1 d . . . H12A H 0.3675 0.2955 -0.2197 0.034 Uiso 1 1 calc R . . C13 C 1.1674(2) -0.06247(13) 0.19752(16) 0.0276(5) Uani 1 1 d . . . C14 C 0.9435(3) 0.39822(14) 0.00313(16) 0.0295(5) Uani 1 1 d . . . H14A H 1.0102 0.3714 -0.0144 0.035 Uiso 1 1 calc R . . C15 C 0.8051(3) 0.39771(13) -0.04858(15) 0.0271(5) Uani 1 1 d . . . C16 C 0.5347(3) 0.11222(14) 0.00757(17) 0.0342(6) Uani 1 1 d . . . H16A H 0.5697 0.0988 -0.0390 0.041 Uiso 1 1 calc R . . C18 C 1.0817(2) -0.02186(12) 0.23543(17) 0.0249(5) Uani 1 1 d . . . H18A H 1.1179 0.0192 0.2691 0.030 Uiso 1 1 calc R . . C19 C 0.5627(2) 0.28929(14) -0.23955(15) 0.0284(5) Uani 1 1 d . . . H19A H 0.6297 0.2501 -0.2397 0.034 Uiso 1 1 calc R . . C20 C 0.4525(3) 0.17414(14) 0.00107(16) 0.0296(5) Uani 1 1 d . . . C22 C 1.3174(2) -0.03987(13) 0.21064(16) 0.0259(5) Uani 1 1 d . . . C23 C 0.3498(3) 0.21031(15) -0.30753(18) 0.0399(6) Uani 1 1 d . . . H23A H 0.4047 0.1675 -0.3118 0.048 Uiso 1 1 calc R . . H23B H 0.2616 0.1939 -0.2997 0.048 Uiso 1 1 calc R . . C25 C 0.4161(3) 0.22638(14) -0.07696(16) 0.0319(6) Uani 1 1 d . . . C26 C 0.5642(3) 0.07032(14) 0.08445(16) 0.0326(6) Uani 1 1 d . . . H26A H 0.6209 0.0293 0.0884 0.039 Uiso 1 1 calc R . . C27 C 0.8902(3) -0.10321(17) 0.1737(2) 0.0479(8) Uani 1 1 d . . . H27A H 0.7969 -0.1164 0.1644 0.058 Uiso 1 1 calc R . . C28 C 0.7127(3) 0.44340(16) -0.02204(17) 0.0391(6) Uani 1 1 d . . . H28A H 0.6199 0.4475 -0.0567 0.047 Uiso 1 1 calc R . . C29 C 0.4330(3) 0.14518(17) 0.14545(19) 0.0467(7) Uani 1 1 d . . . H29A H 0.3967 0.1566 0.1921 0.056 Uiso 1 1 calc R . . C30 C 0.3212(4) 0.25387(17) -0.39272(19) 0.0509(8) Uani 1 1 d . . . H30A H 0.2588 0.2941 -0.3908 0.061 Uiso 1 1 calc R . . H30B H 0.2749 0.2229 -0.4426 0.061 Uiso 1 1 calc R . . C31 C 0.5319(3) 0.33115(15) -0.32731(18) 0.0426(7) Uani 1 1 d . . . H31A H 0.4748 0.3735 -0.3247 0.051 Uiso 1 1 calc R . . H31B H 0.6193 0.3482 -0.3357 0.051 Uiso 1 1 calc R . . C32 C 0.9429(2) -0.04161(14) 0.22378(16) 0.0288(5) Uani 1 1 d . . . C33 C 0.9829(2) 0.43835(13) 0.08058(16) 0.0299(5) Uani 1 1 d . . . H33A H 1.0763 0.4373 0.1146 0.036 Uiso 1 1 calc R . . C34 C 0.7598(3) 0.48233(16) 0.05584(18) 0.0398(7) Uani 1 1 d . . . H34A H 0.6966 0.5125 0.0725 0.048 Uiso 1 1 calc R . . C35 C 0.4003(3) 0.18975(17) 0.07153(19) 0.0465(7) Uani 1 1 d . . . H35A H 0.3431 0.2303 0.0691 0.056 Uiso 1 1 calc R . . C36 C 1.1144(3) -0.12499(16) 0.1490(2) 0.0456(7) Uani 1 1 d . . . H36A H 1.1716 -0.1531 0.1245 0.055 Uiso 1 1 calc R . . C37 C 0.9761(3) -0.14531(19) 0.1374(3) 0.0606(10) Uani 1 1 d . . . H37A H 0.9408 -0.1872 0.1052 0.073 Uiso 1 1 calc R . . C38 C 0.4557(4) 0.28359(18) -0.40597(19) 0.0559(9) Uani 1 1 d . . . H38A H 0.4342 0.3122 -0.4602 0.067 Uiso 1 1 calc R . . H38B H 0.5157 0.2434 -0.4119 0.067 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 0.01266(18) 0.0368(2) 0.02616(19) 0.00509(11) 0.00586(12) 0.00121(11) N1 0.0209(10) 0.0411(12) 0.0299(11) 0.0077(9) 0.0080(9) 0.0032(9) O1 0.0824(17) 0.0643(14) 0.0454(12) 0.0193(11) 0.0294(12) 0.0471(13) O1W 0.0402(12) 0.0490(12) 0.0575(13) -0.0160(10) 0.0173(10) -0.0096(9) N2 0.0309(11) 0.0294(11) 0.0323(11) 0.0061(9) 0.0097(9) 0.0057(9) O2 0.0279(10) 0.0431(10) 0.0520(12) -0.0165(9) 0.0119(9) 0.0009(8) O3 0.0115(8) 0.0453(10) 0.0390(10) 0.0012(8) 0.0081(7) 0.0015(7) N3 0.0247(11) 0.0349(11) 0.0319(11) -0.0082(9) 0.0086(9) -0.0013(9) O4 0.0248(9) 0.0408(10) 0.0523(12) -0.0097(9) 0.0192(8) -0.0054(8) N4 0.0222(11) 0.0349(11) 0.0260(11) -0.0022(8) 0.0071(9) 0.0006(8) O5 0.0212(9) 0.0487(11) 0.0510(12) -0.0098(9) 0.0165(8) 0.0063(8) O6 0.0133(8) 0.0344(9) 0.0337(9) -0.0018(7) 0.0067(7) -0.0008(6) C9 0.0154(11) 0.0326(13) 0.0307(13) 0.0074(11) 0.0082(10) 0.0029(10) C10 0.0250(12) 0.0278(12) 0.0276(12) -0.0001(10) 0.0093(10) -0.0002(10) C12 0.0261(13) 0.0291(12) 0.0284(13) 0.0021(10) 0.0071(10) 0.0008(10) C13 0.0167(11) 0.0351(13) 0.0312(13) -0.0013(10) 0.0071(10) 0.0015(10) C14 0.0242(12) 0.0353(13) 0.0311(13) -0.0022(10) 0.0113(10) 0.0036(10) C15 0.0251(12) 0.0303(12) 0.0260(12) 0.0014(10) 0.0074(10) 0.0008(10) C16 0.0378(15) 0.0362(14) 0.0308(13) 0.0003(11) 0.0138(11) 0.0059(11) C18 0.0153(12) 0.0274(12) 0.0321(13) -0.0024(9) 0.0067(10) -0.0004(9) C19 0.0276(13) 0.0308(13) 0.0270(13) -0.0045(10) 0.0083(10) 0.0000(10) C20 0.0227(12) 0.0356(13) 0.0289(13) 0.0036(10) 0.0049(10) 0.0008(10) C22 0.0168(11) 0.0367(13) 0.0241(12) 0.0040(10) 0.0057(9) 0.0043(10) C23 0.0362(15) 0.0387(15) 0.0383(15) -0.0045(12) 0.0006(12) -0.0078(12) C25 0.0264(13) 0.0375(14) 0.0305(13) 0.0047(11) 0.0059(10) 0.0047(11) C26 0.0319(14) 0.0326(13) 0.0330(14) 0.0022(10) 0.0087(11) 0.0055(11) C27 0.0193(13) 0.0520(17) 0.074(2) -0.0210(15) 0.0159(14) -0.0110(12) C28 0.0226(13) 0.0554(17) 0.0336(14) -0.0123(13) -0.0009(11) 0.0082(12) C29 0.0446(17) 0.0633(19) 0.0392(15) 0.0142(14) 0.0232(13) 0.0245(15) C30 0.056(2) 0.0500(18) 0.0334(15) -0.0058(13) -0.0075(14) -0.0006(15) C31 0.0572(19) 0.0414(15) 0.0334(14) -0.0002(12) 0.0194(13) -0.0117(14) C32 0.0163(12) 0.0334(13) 0.0377(15) -0.0006(10) 0.0093(11) 0.0008(9) C33 0.0193(12) 0.0405(14) 0.0299(13) -0.0019(11) 0.0071(10) -0.0019(10) C34 0.0271(14) 0.0533(17) 0.0367(15) -0.0098(12) 0.0057(12) 0.0120(12) C35 0.0466(17) 0.0544(17) 0.0433(16) 0.0127(14) 0.0206(14) 0.0268(14) C36 0.0271(14) 0.0486(17) 0.0636(19) -0.0225(14) 0.0174(14) -0.0018(12) C37 0.0326(16) 0.0596(19) 0.091(3) -0.0397(19) 0.0210(17) -0.0137(15) C38 0.087(3) 0.0525(18) 0.0276(15) -0.0018(13) 0.0151(16) -0.0051(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 use d 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 O3 1.9427(17) . ? Cu1 O6 1.9854(16) 1_455 ? Cu1 N4 2.046(2) 2_645 ? Cu1 N1 2.0463(19) . ? Cu1 O1W 2.2787(19) . ? N1 C26 1.335(3) . ? N1 C29 1.342(3) . ? O1 C25 1.232(3) . ? N2 C25 1.324(3) . ? N2 C12 1.463(3) . ? O2 C10 1.234(3) . ? O3 C9 1.281(3) . ? N3 C10 1.336(3) . ? N3 C19 1.464(3) . ? O4 C9 1.236(3) . ? N4 C34 1.341(3) . ? N4 C33 1.345(3) . ? N4 Cu1 2.046(2) 2_655 ? O5 C22 1.244(3) . ? O6 C22 1.278(3) . ? O6 Cu1 1.9854(16) 1_655 ? C9 C32 1.510(3) . ? C10 C15 1.516(3) . ? C12 C23 1.530(3) . ? C12 C19 1.534(3) . ? C13 C18 1.389(3) . ? C13 C36 1.392(4) . ? C13 C22 1.507(3) . ? C14 C33 1.378(3) . ? C14 C15 1.384(3) . ? C15 C28 1.394(3) . ? C16 C20 1.385(3) . ? C16 C26 1.389(3) . ? C18 C32 1.390(3) . ? C19 C31 1.530(3) . ? C20 C35 1.382(4) . ? C20 C25 1.514(3) . ? C23 C30 1.513(4) . ? C27 C32 1.389(4) . ? C27 C37 1.391(4) . ? C28 C34 1.377(4) . ? C29 C35 1.380(4) . ? C30 C38 1.515(5) . ? C31 C38 1.523(4) . ? C36 C37 1.387(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O6 145.60(7) . 1_455 ? O3 Cu1 N4 91.79(8) . 2_645 ? O6 Cu1 N4 91.12(8) 1_455 2_645 ? O3 Cu1 N1 91.33(8) . . ? O6 Cu1 N1 89.04(7) 1_455 . ? N4 Cu1 N1 174.24(8) 2_645 . ? O3 Cu1 O1W 113.29(7) . . ? O6 Cu1 O1W 101.09(7) 1_455 . ? N4 Cu1 O1W 87.30(8) 2_645 . ? N1 Cu1 O1W 87.02(8) . . ? C26 N1 C29 117.4(2) . . ? C26 N1 Cu1 124.32(17) . . ? C29 N1 Cu1 118.26(17) . . ? C25 N2 C12 123.3(2) . . ? C9 O3 Cu1 130.51(17) . . ? C10 N3 C19 124.0(2) . . ? C34 N4 C33 116.9(2) . . ? C34 N4 Cu1 118.86(17) . 2_655 ? C33 N4 Cu1 124.00(17) . 2_655 ? C22 O6 Cu1 106.04(14) . 1_655 ? O4 C9 O3 125.1(2) . . ? O4 C9 C32 120.7(2) . . ? O3 C9 C32 114.2(2) . . ? O2 C10 N3 123.5(2) . . ? O2 C10 C15 120.3(2) . . ? N3 C10 C15 116.1(2) . . ? N2 C12 C23 110.1(2) . . ? N2 C12 C19 110.9(2) . . ? C23 C12 C19 111.6(2) . . ? C18 C13 C36 119.5(2) . . ? C18 C13 C22 120.1(2) . . ? C36 C13 C22 120.3(2) . . ? C33 C14 C15 120.2(2) . . ? C14 C15 C28 116.9(2) . . ? C14 C15 C10 118.7(2) . . ? C28 C15 C10 124.3(2) . . ? C20 C16 C26 119.2(2) . . ? C13 C18 C32 121.0(2) . . ? N3 C19 C31 110.0(2) . . ? N3 C19 C12 108.75(18) . . ? C31 C19 C12 111.3(2) . . ? C35 C20 C16 117.5(2) . . ? C35 C20 C25 117.4(2) . . ? C16 C20 C25 125.1(2) . . ? O5 C22 O6 123.5(2) . . ? O5 C22 C13 120.0(2) . . ? O6 C22 C13 116.5(2) . . ? C30 C23 C12 111.6(2) . . ? O1 C25 N2 123.4(2) . . ? O1 C25 C20 118.4(2) . . ? N2 C25 C20 118.2(2) . . ? N1 C26 C16 123.1(2) . . ? C32 C27 C37 120.4(2) . . ? C34 C28 C15 119.5(2) . . ? N1 C29 C35 122.7(2) . . ? C23 C30 C38 111.3(3) . . ? C38 C31 C19 111.6(2) . . ? C27 C32 C18 119.0(2) . . ? C27 C32 C9 120.9(2) . . ? C18 C32 C9 120.1(2) . . ? N4 C33 C14 122.7(2) . . ? N4 C34 C28 123.5(2) . . ? C29 C35 C20 120.0(3) . . ? C37 C36 C13 119.9(2) . . ? C36 C37 C27 120.2(3) . . ? C30 C38 C31 110.3(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.800 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 905478' ####################################################################### # # 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_lj-9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 Cu2 N4 O11' _chemical_formula_weight 797.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8769(11) _cell_length_b 12.6544(14) _cell_length_c 16.4665(18) _cell_angle_alpha 109.065(2) _cell_angle_beta 91.359(2) _cell_angle_gamma 106.942(2) _cell_volume 1844.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.15 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.685 _exptl_absorpt_correction_T_max 0.794 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9689 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6451 _reflns_number_gt 5370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0627P)^2^+0.5659P] 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 6451 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 0.49351(3) 0.10972(3) 0.021312(19) 0.02388(11) Uani 1 1 d . . . O1 O 0.2953(2) 0.01623(18) -0.03334(14) 0.0398(5) Uani 1 1 d . . . N1 N -0.2852(3) -0.5795(2) -0.49509(16) 0.0368(6) Uani 1 1 d . . . O1W O 0.0193(3) -0.3226(3) -0.7100(3) 0.1000(12) Uani 1 1 d . . . H1WA H 0.0633 -0.3698 -0.7064 0.120 Uiso 1 1 d R . . H1WB H 0.0554 -0.2919 -0.7466 0.120 Uiso 1 1 d R . . Cu2 Cu -0.33315(4) -0.61292(3) -0.38764(2) 0.03262(12) Uani 1 1 d . . . O2 O 0.3029(2) -0.16848(17) -0.06994(14) 0.0375(5) Uani 1 1 d . . . N2 N -0.2251(3) -0.2920(2) -0.62838(17) 0.0410(6) Uani 1 1 d . . . H2A H -0.1503 -0.3109 -0.6440 0.049 Uiso 1 1 calc R . . O3 O -0.2943(2) -0.45040(17) -0.31324(13) 0.0385(5) Uani 1 1 d . . . N3 N -0.3568(3) -0.3082(2) -0.79056(16) 0.0379(6) Uani 1 1 d . . . H3A H -0.4434 -0.3070 -0.7899 0.045 Uiso 1 1 calc R . . N4 N -0.5468(3) -0.7222(2) -0.95037(15) 0.0324(5) Uani 1 1 d . . . O4 O -0.0917(2) -0.4841(2) -0.29030(17) 0.0535(6) Uani 1 1 d . . . O5 O -0.3719(2) -0.69587(17) -0.29931(12) 0.0356(5) Uani 1 1 d . . . C5 C -0.4138(3) -0.9990(2) -0.23741(17) 0.0301(6) Uani 1 1 d . . . O6 O -0.3315(3) -0.78017(19) -0.43019(13) 0.0449(6) Uani 1 1 d . . . O7 O -0.4495(2) -1.09176(17) -0.13312(12) 0.0334(4) Uani 1 1 d . . . O8 O -0.4501(2) -0.90455(17) -0.09438(12) 0.0384(5) Uani 1 1 d . . . O9 O -0.4262(2) -0.33865(19) -0.56682(14) 0.0427(5) Uani 1 1 d . . . C9 C -0.3856(3) -0.8949(2) -0.25412(17) 0.0313(6) Uani 1 1 d . . . H9A H -0.3754 -0.8245 -0.2092 0.038 Uiso 1 1 calc R . . O10 O -0.2124(3) -0.4136(2) -0.8497(2) 0.0716(8) Uani 1 1 d . . . C13 C -0.3559(3) -0.7854(3) -0.35660(18) 0.0327(6) Uani 1 1 d . . . C14 C -0.2794(3) -0.4614(3) -0.58354(19) 0.0366(7) Uani 1 1 d . . . C15 C -0.2518(4) -0.0933(3) -0.7538(2) 0.0462(8) Uani 1 1 d . . . H15A H -0.3454 -0.0854 -0.7440 0.055 Uiso 1 1 calc R . . H15B H -0.2410 -0.1024 -0.8139 0.055 Uiso 1 1 calc R . . C16 C -0.3724(3) -0.8955(3) -0.33824(18) 0.0349(7) Uani 1 1 d . . . C17 C 0.0924(3) -0.1381(2) -0.11577(17) 0.0286(6) Uani 1 1 d . . . C20 C -0.2453(4) -0.1885(3) -0.6421(2) 0.0393(7) Uani 1 1 d . . . H20A H -0.3390 -0.1836 -0.6265 0.047 Uiso 1 1 calc R . . C21 C 0.0311(3) -0.2551(2) -0.16893(17) 0.0304(6) Uani 1 1 d . . . H21A H 0.0808 -0.3085 -0.1735 0.037 Uiso 1 1 calc R . . C22 C -0.4616(3) -0.5112(2) -0.88384(19) 0.0347(7) Uani 1 1 d . . . C25 C 0.2410(3) -0.0943(2) -0.06922(16) 0.0290(6) Uani 1 1 d . . . C26 C -0.1659(3) -0.4186(3) -0.27617(19) 0.0350(7) Uani 1 1 d . . . C28 C -0.1041(3) -0.2930(2) -0.21533(18) 0.0314(6) Uani 1 1 d . . . C29 C -0.4427(3) -0.6218(2) -0.90947(19) 0.0362(7) Uani 1 1 d . . . H29A H -0.3523 -0.6258 -0.8973 0.043 Uiso 1 1 calc R . . C30 C -0.4396(3) -0.9983(2) -0.14761(17) 0.0288(6) Uani 1 1 d . . . C31 C -0.5977(3) -0.5069(3) -0.9023(2) 0.0421(7) Uani 1 1 d . . . H31A H -0.6157 -0.4351 -0.8855 0.051 Uiso 1 1 calc R . . C32 C -0.4266(4) -1.1035(3) -0.30442(19) 0.0414(7) Uani 1 1 d . . . H32A H -0.4459 -1.1735 -0.2931 0.050 Uiso 1 1 calc R . . C34 C 0.0153(3) -0.0598(3) -0.10828(19) 0.0373(7) Uani 1 1 d . . . H34A H 0.0556 0.0189 -0.0732 0.045 Uiso 1 1 calc R . . C35 C -0.2422(3) -0.2021(2) -0.73746(19) 0.0349(7) Uani 1 1 d . . . H35A H -0.1510 -0.2129 -0.7535 0.042 Uiso 1 1 calc R . . C36 C -0.3333(4) -0.4065(3) -0.8398(2) 0.0407(7) Uani 1 1 d . . . C37 C -0.1800(3) -0.2142(3) -0.2054(2) 0.0409(7) Uani 1 1 d . . . H37A H -0.2718 -0.2398 -0.2347 0.049 Uiso 1 1 calc R . . C38 C -0.3167(3) -0.3577(2) -0.59313(18) 0.0339(7) Uani 1 1 d . . . C39 C -0.3100(3) -0.4881(2) -0.50978(19) 0.0343(6) Uani 1 1 d . . . H39A H -0.3497 -0.4405 -0.4683 0.041 Uiso 1 1 calc R . . C41 C -0.1205(3) -0.0979(3) -0.1525(2) 0.0452(8) Uani 1 1 d . . . H41A H -0.1717 -0.0453 -0.1465 0.054 Uiso 1 1 calc R . . C42 C -0.4110(4) -1.1045(3) -0.3877(2) 0.0531(9) Uani 1 1 d . . . H42A H -0.4186 -1.1747 -0.4322 0.064 Uiso 1 1 calc R . . C43 C -0.1315(4) -0.0769(3) -0.5847(2) 0.0544(9) Uani 1 1 d . . . H43A H -0.0379 -0.0834 -0.5965 0.065 Uiso 1 1 calc R . . H43B H -0.1390 -0.0684 -0.5244 0.065 Uiso 1 1 calc R . . C44 C -0.7044(4) -0.6093(3) -0.9454(2) 0.0466(8) Uani 1 1 d . . . H44A H -0.7956 -0.6080 -0.9592 0.056 Uiso 1 1 calc R . . C45 C -0.6759(3) -0.7139(3) -0.9680(2) 0.0409(7) Uani 1 1 d . . . H45A H -0.7499 -0.7829 -0.9971 0.049 Uiso 1 1 calc R . . C46 C -0.3839(4) -1.0005(3) -0.40474(19) 0.0463(8) Uani 1 1 d . . . H46A H -0.3733 -1.0010 -0.4608 0.056 Uiso 1 1 calc R . . C47 C -0.1378(4) 0.0179(3) -0.6953(2) 0.0562(9) Uani 1 1 d . . . H47A H -0.1501 0.0859 -0.7058 0.067 Uiso 1 1 calc R . . H47B H -0.0442 0.0135 -0.7090 0.067 Uiso 1 1 calc R . . C48 C -0.2299(5) -0.6484(3) -0.5554(3) 0.0635(12) Uani 1 1 d . . . H48A H -0.2140 -0.7130 -0.5466 0.076 Uiso 1 1 calc R . . C49 C -0.2205(5) -0.5327(3) -0.6450(3) 0.0667(12) Uani 1 1 d . . . H49A H -0.1981 -0.5176 -0.6955 0.080 Uiso 1 1 calc R . . C51 C -0.1960(6) -0.6269(4) -0.6296(3) 0.0887(18) Uani 1 1 d . . . H51A H -0.1562 -0.6759 -0.6699 0.106 Uiso 1 1 calc R . . C52 C -0.1464(5) 0.0335(3) -0.6001(2) 0.0645(11) Uani 1 1 d . . . H52A H -0.2371 0.0437 -0.5847 0.077 Uiso 1 1 calc R . . H52B H -0.0705 0.1030 -0.5640 0.077 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 0.02912(19) 0.02164(18) 0.02115(18) 0.00825(13) 0.00026(13) 0.00776(14) O1 0.0338(11) 0.0326(11) 0.0440(12) 0.0046(10) -0.0092(9) 0.0084(9) N1 0.0447(15) 0.0329(13) 0.0391(14) 0.0203(11) 0.0116(12) 0.0124(12) O1W 0.069(2) 0.098(3) 0.166(4) 0.072(3) 0.027(2) 0.045(2) Cu2 0.0439(2) 0.0280(2) 0.0273(2) 0.01368(15) 0.00196(15) 0.00889(16) O2 0.0312(11) 0.0324(11) 0.0443(12) 0.0119(9) -0.0045(9) 0.0059(9) N2 0.0439(15) 0.0389(14) 0.0478(16) 0.0263(13) 0.0047(12) 0.0117(12) O3 0.0352(11) 0.0331(11) 0.0390(12) 0.0098(9) -0.0086(9) 0.0031(9) N3 0.0393(14) 0.0277(13) 0.0403(14) 0.0051(11) -0.0035(11) 0.0098(11) N4 0.0412(14) 0.0255(12) 0.0308(13) 0.0086(10) 0.0005(10) 0.0129(11) O4 0.0434(13) 0.0370(12) 0.0691(17) 0.0041(11) -0.0036(11) 0.0140(11) O5 0.0488(12) 0.0307(11) 0.0293(11) 0.0137(9) 0.0045(9) 0.0120(10) C5 0.0367(16) 0.0338(15) 0.0249(14) 0.0144(12) 0.0042(12) 0.0139(13) O6 0.0777(16) 0.0395(12) 0.0284(11) 0.0207(10) 0.0160(11) 0.0240(12) O7 0.0455(12) 0.0352(11) 0.0287(10) 0.0186(9) 0.0096(9) 0.0174(9) O8 0.0628(14) 0.0329(11) 0.0249(10) 0.0135(9) 0.0113(10) 0.0187(10) O9 0.0492(14) 0.0414(12) 0.0396(12) 0.0160(10) 0.0046(10) 0.0152(11) C9 0.0406(16) 0.0305(14) 0.0244(14) 0.0101(12) 0.0041(12) 0.0132(13) O10 0.0410(15) 0.0469(15) 0.101(2) -0.0079(14) -0.0004(14) 0.0156(12) C13 0.0404(17) 0.0337(15) 0.0262(15) 0.0133(13) 0.0022(12) 0.0118(13) C14 0.0439(18) 0.0312(15) 0.0360(16) 0.0177(13) 0.0064(13) 0.0068(14) C15 0.060(2) 0.0378(17) 0.0420(18) 0.0230(15) 0.0000(16) 0.0081(16) C16 0.0500(18) 0.0334(15) 0.0270(15) 0.0157(12) 0.0079(13) 0.0158(14) C17 0.0255(14) 0.0340(15) 0.0230(13) 0.0077(12) 0.0035(11) 0.0068(12) C20 0.0462(18) 0.0295(15) 0.0421(18) 0.0166(14) -0.0005(14) 0.0078(14) C21 0.0297(15) 0.0331(15) 0.0300(15) 0.0124(12) 0.0045(12) 0.0107(12) C22 0.0422(17) 0.0276(14) 0.0335(16) 0.0077(12) 0.0024(13) 0.0135(13) C25 0.0289(14) 0.0337(15) 0.0208(13) 0.0073(12) 0.0033(11) 0.0073(13) C26 0.0354(16) 0.0330(15) 0.0333(16) 0.0124(13) 0.0015(13) 0.0054(13) C28 0.0298(15) 0.0335(15) 0.0271(14) 0.0099(12) 0.0019(12) 0.0053(12) C29 0.0374(16) 0.0289(15) 0.0406(17) 0.0090(13) -0.0020(13) 0.0121(13) C30 0.0282(14) 0.0344(15) 0.0262(14) 0.0144(12) 0.0022(11) 0.0093(12) C31 0.0468(19) 0.0286(15) 0.0490(19) 0.0056(14) -0.0030(15) 0.0187(14) C32 0.065(2) 0.0328(16) 0.0328(16) 0.0149(13) 0.0054(15) 0.0211(16) C34 0.0346(16) 0.0334(15) 0.0355(16) 0.0016(13) 0.0017(13) 0.0104(13) C35 0.0370(16) 0.0282(15) 0.0369(16) 0.0111(13) -0.0021(13) 0.0072(13) C36 0.0441(19) 0.0295(16) 0.0439(18) 0.0075(14) -0.0022(14) 0.0115(14) C37 0.0283(15) 0.0435(18) 0.0449(18) 0.0103(15) -0.0037(13) 0.0091(14) C38 0.0419(18) 0.0297(15) 0.0242(14) 0.0097(12) -0.0047(12) 0.0031(13) C39 0.0421(17) 0.0280(14) 0.0322(15) 0.0119(12) 0.0022(13) 0.0092(13) C41 0.0374(18) 0.0415(18) 0.053(2) 0.0051(15) 0.0001(15) 0.0200(15) C42 0.098(3) 0.0387(18) 0.0292(17) 0.0100(14) 0.0121(17) 0.0331(19) C43 0.069(2) 0.0396(18) 0.0414(19) 0.0145(16) -0.0114(17) -0.0013(17) C44 0.0389(18) 0.0389(18) 0.059(2) 0.0101(16) -0.0047(15) 0.0172(15) C45 0.0433(18) 0.0306(16) 0.0420(18) 0.0070(13) -0.0039(14) 0.0092(14) C46 0.079(2) 0.0469(18) 0.0240(15) 0.0165(14) 0.0150(15) 0.0303(18) C47 0.074(3) 0.0320(17) 0.059(2) 0.0235(16) 0.0034(19) 0.0023(17) C48 0.098(3) 0.055(2) 0.073(3) 0.045(2) 0.049(2) 0.048(2) C49 0.112(4) 0.060(2) 0.061(2) 0.043(2) 0.052(2) 0.048(2) C51 0.158(5) 0.076(3) 0.089(3) 0.058(3) 0.087(3) 0.081(3) C52 0.091(3) 0.0303(18) 0.056(2) 0.0107(17) -0.004(2) 0.0014(19) _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 O8 1.9637(19) 1_665 ? Cu1 O7 1.9707(18) 2_545 ? Cu1 O2 1.975(2) 2_655 ? Cu1 O1 1.978(2) . ? Cu1 N4 2.181(2) 1_666 ? Cu1 Cu1 2.6756(7) 2_655 ? O1 C25 1.266(3) . ? N1 C48 1.335(4) . ? N1 C39 1.342(4) . ? N1 Cu2 1.986(2) . ? Cu2 O3 1.936(2) . ? Cu2 O6 2.006(2) . ? Cu2 O5 2.0380(19) . ? Cu2 O9 2.314(2) 2_444 ? Cu2 C13 2.350(3) . ? O2 C25 1.257(3) . ? O2 Cu1 1.975(2) 2_655 ? N2 C38 1.323(4) . ? N2 C20 1.466(4) . ? O3 C26 1.283(4) . ? N3 C36 1.333(4) . ? N3 C35 1.466(4) . ? N4 C29 1.331(4) . ? N4 C45 1.342(4) . ? N4 Cu1 2.181(2) 1_444 ? O4 C26 1.231(4) . ? O5 C13 1.269(3) . ? C5 C9 1.384(4) . ? C5 C32 1.388(4) . ? C5 C30 1.504(4) . ? O6 C13 1.260(3) . ? O7 C30 1.258(3) . ? O7 Cu1 1.9707(18) 2_545 ? O8 C30 1.259(3) . ? O8 Cu1 1.9637(19) 1_445 ? O9 C38 1.233(4) . ? O9 Cu2 2.314(2) 2_444 ? C9 C16 1.392(4) . ? O10 C36 1.234(4) . ? C13 C16 1.485(4) . ? C14 C39 1.381(4) . ? C14 C49 1.384(5) . ? C14 C38 1.515(4) . ? C15 C35 1.515(4) . ? C15 C47 1.522(5) . ? C16 C46 1.391(4) . ? C17 C21 1.389(4) . ? C17 C34 1.394(4) . ? C17 C25 1.498(4) . ? C20 C43 1.518(4) . ? C20 C35 1.525(4) . ? C21 C28 1.391(4) . ? C22 C31 1.392(4) . ? C22 C29 1.394(4) . ? C22 C36 1.495(4) . ? C26 C28 1.506(4) . ? C28 C37 1.385(4) . ? C31 C44 1.364(5) . ? C32 C42 1.380(4) . ? C34 C41 1.381(4) . ? C37 C41 1.380(4) . ? C42 C46 1.386(4) . ? C43 C52 1.545(5) . ? C44 C45 1.367(4) . ? C47 C52 1.523(5) . ? C48 C51 1.365(5) . ? C49 C51 1.382(5) . ? 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 O8 Cu1 O7 167.02(8) 1_665 2_545 ? O8 Cu1 O2 89.47(9) 1_665 2_655 ? O7 Cu1 O2 87.18(9) 2_545 2_655 ? O8 Cu1 O1 89.10(9) 1_665 . ? O7 Cu1 O1 91.40(9) 2_545 . ? O2 Cu1 O1 167.30(8) 2_655 . ? O8 Cu1 N4 97.15(8) 1_665 1_666 ? O7 Cu1 N4 95.76(8) 2_545 1_666 ? O2 Cu1 N4 99.23(9) 2_655 1_666 ? O1 Cu1 N4 93.47(9) . 1_666 ? O8 Cu1 Cu1 83.30(6) 1_665 2_655 ? O7 Cu1 Cu1 84.06(6) 2_545 2_655 ? O2 Cu1 Cu1 88.28(6) 2_655 2_655 ? O1 Cu1 Cu1 79.02(6) . 2_655 ? N4 Cu1 Cu1 172.47(7) 1_666 2_655 ? C25 O1 Cu1 128.96(18) . . ? C48 N1 C39 118.2(3) . . ? C48 N1 Cu2 121.0(2) . . ? C39 N1 Cu2 120.8(2) . . ? O3 Cu2 N1 96.34(10) . . ? O3 Cu2 O6 160.21(9) . . ? N1 Cu2 O6 96.86(9) . . ? O3 Cu2 O5 100.75(8) . . ? N1 Cu2 O5 161.85(9) . . ? O6 Cu2 O5 65.06(8) . . ? O3 Cu2 O9 99.95(8) . 2_444 ? N1 Cu2 O9 90.28(9) . 2_444 ? O6 Cu2 O9 94.67(9) . 2_444 ? O5 Cu2 O9 92.73(8) . 2_444 ? O3 Cu2 C13 131.87(9) . . ? N1 Cu2 C13 129.24(10) . . ? O6 Cu2 C13 32.42(9) . . ? O5 Cu2 C13 32.64(9) . . ? O9 Cu2 C13 94.96(9) 2_444 . ? C25 O2 Cu1 118.26(18) . 2_655 ? C38 N2 C20 122.9(3) . . ? C26 O3 Cu2 105.04(18) . . ? C36 N3 C35 123.2(3) . . ? C29 N4 C45 116.9(2) . . ? C29 N4 Cu1 119.94(19) . 1_444 ? C45 N4 Cu1 123.0(2) . 1_444 ? C13 O5 Cu2 87.32(16) . . ? C9 C5 C32 119.9(3) . . ? C9 C5 C30 119.3(2) . . ? C32 C5 C30 120.8(2) . . ? C13 O6 Cu2 89.00(17) . . ? C30 O7 Cu1 122.45(18) . 2_545 ? C30 O8 Cu1 123.55(17) . 1_445 ? C38 O9 Cu2 141.15(19) . 2_444 ? C5 C9 C16 120.0(3) . . ? O6 C13 O5 118.6(2) . . ? O6 C13 C16 120.9(3) . . ? O5 C13 C16 120.5(2) . . ? O6 C13 Cu2 58.58(14) . . ? O5 C13 Cu2 60.03(14) . . ? C16 C13 Cu2 179.0(2) . . ? C39 C14 C49 118.1(3) . . ? C39 C14 C38 117.7(3) . . ? C49 C14 C38 124.2(3) . . ? C35 C15 C47 111.8(3) . . ? C46 C16 C9 119.6(3) . . ? C46 C16 C13 120.9(3) . . ? C9 C16 C13 119.3(3) . . ? C21 C17 C34 119.0(3) . . ? C21 C17 C25 121.2(2) . . ? C34 C17 C25 119.7(2) . . ? N2 C20 C43 110.4(3) . . ? N2 C20 C35 109.7(2) . . ? C43 C20 C35 111.0(3) . . ? C17 C21 C28 120.5(3) . . ? C31 C22 C29 117.4(3) . . ? C31 C22 C36 125.3(3) . . ? C29 C22 C36 117.3(3) . . ? O2 C25 O1 125.2(3) . . ? O2 C25 C17 118.4(2) . . ? O1 C25 C17 116.4(2) . . ? O4 C26 O3 123.2(3) . . ? O4 C26 C28 119.7(3) . . ? O3 C26 C28 117.1(3) . . ? C37 C28 C21 119.5(3) . . ? C37 C28 C26 120.7(3) . . ? C21 C28 C26 119.8(3) . . ? N4 C29 C22 123.7(3) . . ? O7 C30 O8 126.3(2) . . ? O7 C30 C5 116.9(2) . . ? O8 C30 C5 116.8(2) . . ? C44 C31 C22 119.1(3) . . ? C42 C32 C5 120.5(3) . . ? C41 C34 C17 120.6(3) . . ? N3 C35 C15 111.8(2) . . ? N3 C35 C20 109.5(2) . . ? C15 C35 C20 111.7(3) . . ? O10 C36 N3 122.9(3) . . ? O10 C36 C22 120.1(3) . . ? N3 C36 C22 117.0(3) . . ? C41 C37 C28 120.5(3) . . ? O9 C38 N2 124.6(3) . . ? O9 C38 C14 119.3(3) . . ? N2 C38 C14 116.1(3) . . ? N1 C39 C14 123.1(3) . . ? C37 C41 C34 119.9(3) . . ? C32 C42 C46 119.8(3) . . ? C20 C43 C52 111.7(3) . . ? C31 C44 C45 119.4(3) . . ? N4 C45 C44 123.5(3) . . ? C42 C46 C16 120.2(3) . . ? C15 C47 C52 111.3(3) . . ? N1 C48 C51 121.9(3) . . ? C51 C49 C14 118.4(3) . . ? C48 C51 C49 120.3(3) . . ? C47 C52 C43 108.9(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.651 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 905479' ####################################################################### # # 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_lj-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Co N4 O7' _chemical_formula_weight 565.44 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8628(6) _cell_length_b 18.1938(11) _cell_length_c 15.8811(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.8580(10) _cell_angle_gamma 90.00 _cell_volume 2727.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour PINK _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172 _exptl_absorpt_coefficient_mu 0.679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8761 _exptl_absorpt_correction_T_max 0.8991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13736 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4808 _reflns_number_gt 4148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _refine_special_details ; Refinement of F^2^ aga inst 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^)+(0.0432P)^2^+0.9702P] 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 4808 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Co1 Co 0.06567(2) 0.031741(13) 0.767162(16) 0.02585(9) Uani 1 1 d . . . O1 O 0.21626(13) -0.02307(8) 0.73426(9) 0.0374(3) Uani 1 1 d . . . N1 N 0.11745(17) -0.02106(8) 0.89653(10) 0.0320(4) Uani 1 1 d . . . C1 C 0.2498(2) -0.01863(13) 0.94917(14) 0.0457(6) Uani 1 1 d . . . H1A H 0.3147 0.0109 0.9326 0.055 Uiso 1 1 calc R . . O1W O 0.10439(15) 0.13283(8) 0.83216(10) 0.0442(4) Uani 1 1 d . . . H1WA H 0.0295 0.1584 0.8235 0.053 Uiso 1 1 d R . . H1WB H 0.1742 0.1600 0.8578 0.053 Uiso 1 1 d R . . O2 O 0.38793(15) 0.05282(8) 0.80528(10) 0.0422(4) Uani 1 1 d . . . N2 N 0.48636(17) -0.40704(9) 0.85641(10) 0.0342(4) Uani 1 1 d . . . C2 C 0.2965(2) -0.05754(13) 1.02700(14) 0.0448(5) Uani 1 1 d . . . H2A H 0.3903 -0.0540 1.0612 0.054 Uiso 1 1 calc R . . O3 O 0.91388(14) -0.07167(8) 0.69436(10) 0.0422(4) Uani 1 1 d . . . C3 C 0.20244(19) -0.10181(10) 1.05357(12) 0.0278(4) Uani 1 1 d . . . N3 N 0.38179(16) -0.16006(8) 1.17187(10) 0.0297(3) Uani 1 1 d . . . H3A H 0.4393 -0.1344 1.1522 0.036 Uiso 1 1 calc R . . C4 C 0.0631(2) -0.10112(10) 1.00169(12) 0.0310(4) Uani 1 1 d . . . H4A H -0.0051 -0.1278 1.0186 0.037 Uiso 1 1 calc R . . O4 O 0.85452(13) 0.02585(7) 0.75684(9) 0.0342(3) Uani 1 1 d . . . N4 N 0.54845(17) -0.28773(8) 1.15728(10) 0.0313(4) Uani 1 1 d . . . H4B H 0.5006 -0.3276 1.1551 0.038 Uiso 1 1 calc R . . O5 O 0.15185(14) -0.18836(7) 1.15344(9) 0.0377(3) Uani 1 1 d . . . C5 C 0.0253(2) -0.06073(11) 0.92471(12) 0.0317(4) Uani 1 1 d . . . H5A H -0.0690 -0.0612 0.8908 0.038 Uiso 1 1 calc R . . O6 O 0.65867(19) -0.21338(9) 1.08420(10) 0.0554(4) Uani 1 1 d . . . C6 C 0.24367(19) -0.15312(9) 1.13203(12) 0.0267(4) Uani 1 1 d . . . C7 C 0.4422(2) -0.20851(10) 1.24691(11) 0.0290(4) Uani 1 1 d . . . H7A H 0.3742 -0.2478 1.2468 0.035 Uiso 1 1 calc R . . C8 C 0.4707(3) -0.16576(11) 1.33316(13) 0.0430(5) Uani 1 1 d . . . H8A H 0.5290 -0.1233 1.3310 0.052 Uiso 1 1 calc R . . H8B H 0.3816 -0.1483 1.3401 0.052 Uiso 1 1 calc R . . C9 C 0.5455(3) -0.21329(13) 1.41210(14) 0.0550(6) Uani 1 1 d . . . H9A H 0.5663 -0.1840 1.4654 0.066 Uiso 1 1 calc R . . H9B H 0.4837 -0.2533 1.4178 0.066 Uiso 1 1 calc R . . C10 C 0.6819(3) -0.24430(13) 1.40113(14) 0.0496(6) Uani 1 1 d . . . H10A H 0.7462 -0.2043 1.3996 0.060 Uiso 1 1 calc R . . H10B H 0.7269 -0.2753 1.4512 0.060 Uiso 1 1 calc R . . C11 C 0.6542(2) -0.28878(11) 1.31740(13) 0.0403(5) Uani 1 1 d . . . H11A H 0.5966 -0.3312 1.3211 0.048 Uiso 1 1 calc R . . H11B H 0.7435 -0.3064 1.3109 0.048 Uiso 1 1 calc R . . C12 C 0.5783(2) -0.24286(10) 1.23691(12) 0.0282(4) Uani 1 1 d . . . H12A H 0.6418 -0.2029 1.2314 0.034 Uiso 1 1 calc R . . C13 C 0.5916(2) -0.26993(10) 1.08809(12) 0.0310(4) Uani 1 1 d . . . C14 C 0.55443(19) -0.32131(10) 1.00973(12) 0.0306(4) Uani 1 1 d . . . C15 C 0.4744(2) -0.38457(10) 1.00286(13) 0.0358(4) Uani 1 1 d . . . H15A H 0.4421 -0.3999 1.0495 0.043 Uiso 1 1 calc R . . C16 C 0.4427(2) -0.42486(10) 0.92549(12) 0.0352(5) Uani 1 1 d . . . H16A H 0.3876 -0.4669 0.9217 0.042 Uiso 1 1 calc R . . C17 C 0.6019(3) -0.30295(14) 0.93884(15) 0.0520(6) Uani 1 1 d . . . H17A H 0.6574 -0.2612 0.9411 0.062 Uiso 1 1 calc R . . C18 C 0.5669(3) -0.34676(14) 0.86436(15) 0.0538(6) Uani 1 1 d . . . H18A H 0.6010 -0.3337 0.8176 0.065 Uiso 1 1 calc R . . C19 C 0.34403(19) -0.00134(10) 0.75743(12) 0.0290(4) Uani 1 1 d . . . C20 C 0.44425(19) -0.04652(10) 0.72246(12) 0.0285(4) Uani 1 1 d . . . C21 C 0.3991(2) -0.11085(12) 0.67538(16) 0.0453(5) Uani 1 1 d . . . H21A H 0.3060 -0.1265 0.6654 0.054 Uiso 1 1 calc R . . C22 C 0.4918(2) -0.15183(13) 0.64321(18) 0.0541(7) Uani 1 1 d . . . H22A H 0.4612 -0.1953 0.6127 0.065 Uiso 1 1 calc R . . C23 C 0.6299(2) -0.12817(11) 0.65646(15) 0.0420(5) Uani 1 1 d . . . H23A H 0.6919 -0.1556 0.6347 0.050 Uiso 1 1 calc R . . C24 C 0.67573(18) -0.06336(10) 0.70240(12) 0.0269(4) Uani 1 1 d . . . C25 C 0.58268(19) -0.02364(9) 0.73559(12) 0.0261(4) Uani 1 1 d . . . H25A H 0.6139 0.0192 0.7673 0.031 Uiso 1 1 calc R . . C26 C 0.82339(19) -0.03531(10) 0.71765(12) 0.0278(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01900(14) 0.03107(15) 0.02897(15) 0.00292(10) 0.00931(10) 0.00182(10) O1 0.0201(7) 0.0468(8) 0.0482(8) 0.0016(6) 0.0143(6) 0.0038(6) N1 0.0331(9) 0.0345(9) 0.0286(8) 0.0014(7) 0.0094(7) 0.0003(7) C1 0.0362(12) 0.0580(14) 0.0405(12) 0.0154(10) 0.0072(10) -0.0119(10) O1W 0.0310(8) 0.0389(8) 0.0617(10) -0.0132(7) 0.0119(7) -0.0055(6) O2 0.0404(8) 0.0365(8) 0.0591(10) -0.0084(7) 0.0292(7) -0.0019(6) N2 0.0314(9) 0.0389(9) 0.0340(9) -0.0071(7) 0.0121(7) -0.0045(7) C2 0.0309(11) 0.0588(14) 0.0390(12) 0.0151(10) 0.0009(9) -0.0097(10) O3 0.0236(7) 0.0519(9) 0.0564(9) 0.0012(7) 0.0197(7) 0.0069(6) C3 0.0304(10) 0.0262(9) 0.0277(9) -0.0021(7) 0.0096(8) 0.0001(8) N3 0.0282(9) 0.0307(8) 0.0322(8) 0.0064(7) 0.0120(7) 0.0015(7) C4 0.0294(10) 0.0323(10) 0.0335(10) 0.0014(8) 0.0127(8) -0.0008(8) O4 0.0226(7) 0.0385(8) 0.0415(8) -0.0040(6) 0.0095(6) -0.0076(6) N4 0.0358(9) 0.0256(8) 0.0333(9) -0.0058(7) 0.0112(7) -0.0038(7) O5 0.0325(8) 0.0341(7) 0.0478(8) 0.0099(6) 0.0138(6) -0.0014(6) C5 0.0273(10) 0.0379(11) 0.0302(10) 0.0007(8) 0.0088(8) 0.0030(8) O6 0.0731(12) 0.0537(10) 0.0435(9) -0.0161(7) 0.0234(8) -0.0356(9) C6 0.0302(10) 0.0218(9) 0.0302(10) -0.0029(7) 0.0121(8) -0.0003(8) C7 0.0327(10) 0.0267(9) 0.0288(10) 0.0043(7) 0.0105(8) 0.0009(8) C8 0.0623(15) 0.0370(11) 0.0348(11) -0.0007(9) 0.0223(11) 0.0082(10) C9 0.088(2) 0.0487(13) 0.0284(11) 0.0030(10) 0.0167(12) 0.0027(13) C10 0.0605(16) 0.0451(13) 0.0325(12) 0.0072(9) -0.0035(10) -0.0054(11) C11 0.0406(12) 0.0354(11) 0.0393(12) 0.0042(9) 0.0028(9) 0.0064(9) C12 0.0296(10) 0.0252(9) 0.0287(9) -0.0019(7) 0.0068(8) -0.0011(8) C13 0.0283(10) 0.0316(10) 0.0317(10) -0.0045(8) 0.0062(8) -0.0024(8) C14 0.0259(10) 0.0339(10) 0.0316(10) -0.0052(8) 0.0077(8) -0.0003(8) C15 0.0458(12) 0.0326(10) 0.0311(10) -0.0006(8) 0.0144(9) -0.0038(9) C16 0.0434(12) 0.0272(10) 0.0342(11) -0.0025(8) 0.0100(9) -0.0040(9) C17 0.0573(15) 0.0586(15) 0.0466(13) -0.0187(11) 0.0253(11) -0.0326(12) C18 0.0572(15) 0.0696(16) 0.0440(13) -0.0188(12) 0.0293(12) -0.0315(13) C19 0.0230(10) 0.0311(10) 0.0369(10) 0.0093(9) 0.0152(8) 0.0045(8) C20 0.0213(9) 0.0286(10) 0.0374(11) -0.0003(8) 0.0112(8) 0.0007(7) C21 0.0240(10) 0.0439(12) 0.0698(15) -0.0153(11) 0.0166(10) -0.0097(9) C22 0.0355(12) 0.0434(13) 0.0861(18) -0.0318(12) 0.0218(12) -0.0116(10) C23 0.0298(11) 0.0390(11) 0.0613(14) -0.0168(10) 0.0197(10) 0.0007(9) C24 0.0199(9) 0.0285(9) 0.0322(10) -0.0005(8) 0.0076(7) -0.0001(7) C25 0.0232(9) 0.0239(9) 0.0322(10) -0.0026(7) 0.0094(8) -0.0010(7) C26 0.0194(9) 0.0375(11) 0.0262(9) 0.0075(8) 0.0063(7) 0.0034(8) _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 Co1 O1 1.9807(13) . ? Co1 O4 2.0439(13) 1_455 ? Co1 O1W 2.0893(14) . ? Co1 N2 2.1843(16) 2_556 ? Co1 N1 2.1900(15) . ? O1 C19 1.269(2) . ? N1 C1 1.331(3) . ? N1 C5 1.336(2) . ? C1 C2 1.382(3) . ? O2 C19 1.243(2) . ? N2 C16 1.330(2) . ? N2 C18 1.339(3) . ? N2 Co1 2.1843(16) 2_546 ? C2 C3 1.383(3) . ? O3 C26 1.250(2) . ? C3 C4 1.383(3) . ? C3 C6 1.515(2) . ? N3 C6 1.331(2) . ? N3 C7 1.463(2) . ? C4 C5 1.382(3) . ? O4 C26 1.268(2) . ? O4 Co1 2.0439(13) 1_655 ? N4 C13 1.328(2) . ? N4 C12 1.462(2) . ? O5 C6 1.235(2) . ? O6 C13 1.234(2) . ? C7 C8 1.529(3) . ? C7 C12 1.530(3) . ? C8 C9 1.525(3) . ? C9 C10 1.515(4) . ? C10 C11 1.512(3) . ? C11 C12 1.529(3) . ? C13 C14 1.514(3) . ? C14 C17 1.380(3) . ? C14 C15 1.382(3) . ? C15 C16 1.386(3) . ? C17 C18 1.384(3) . ? C19 C20 1.510(2) . ? C20 C25 1.384(3) . ? C20 C21 1.391(3) . ? C21 C22 1.387(3) . ? C22 C23 1.385(3) . ? C23 C24 1.391(3) . ? C24 C25 1.387(2) . ? C24 C26 1.495(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 O1 Co1 O4 140.98(6) . 1_455 ? O1 Co1 O1W 122.00(6) . . ? O4 Co1 O1W 97.00(5) 1_455 . ? O1 Co1 N2 91.06(6) . 2_556 ? O4 Co1 N2 89.21(6) 1_455 2_556 ? O1W Co1 N2 87.52(6) . 2_556 ? O1 Co1 N1 92.17(6) . . ? O4 Co1 N1 90.41(6) 1_455 . ? O1W Co1 N1 87.88(6) . . ? N2 Co1 N1 175.31(6) 2_556 . ? C19 O1 Co1 121.61(13) . . ? C1 N1 C5 116.51(16) . . ? C1 N1 Co1 119.60(13) . . ? C5 N1 Co1 123.73(13) . . ? N1 C1 C2 123.78(19) . . ? C16 N2 C18 116.56(17) . . ? C16 N2 Co1 124.69(13) . 2_546 ? C18 N2 Co1 118.74(13) . 2_546 ? C1 C2 C3 119.48(19) . . ? C4 C3 C2 116.85(17) . . ? C4 C3 C6 118.62(16) . . ? C2 C3 C6 124.45(17) . . ? C6 N3 C7 124.27(15) . . ? C5 C4 C3 119.90(17) . . ? C26 O4 Co1 100.45(11) . 1_655 ? C13 N4 C12 123.17(16) . . ? N1 C5 C4 123.29(17) . . ? O5 C6 N3 123.42(17) . . ? O5 C6 C3 120.19(16) . . ? N3 C6 C3 116.29(15) . . ? N3 C7 C8 110.42(15) . . ? N3 C7 C12 108.89(14) . . ? C8 C7 C12 111.20(16) . . ? C9 C8 C7 111.57(17) . . ? C10 C9 C8 110.51(19) . . ? C11 C10 C9 111.12(19) . . ? C10 C11 C12 111.26(16) . . ? N4 C12 C11 110.19(15) . . ? N4 C12 C7 110.81(15) . . ? C11 C12 C7 111.60(16) . . ? O6 C13 N4 123.33(17) . . ? O6 C13 C14 118.63(17) . . ? N4 C13 C14 118.03(16) . . ? C17 C14 C15 117.29(18) . . ? C17 C14 C13 117.55(17) . . ? C15 C14 C13 125.15(17) . . ? C14 C15 C16 119.14(18) . . ? N2 C16 C15 123.97(18) . . ? C14 C17 C18 119.9(2) . . ? N2 C18 C17 123.1(2) . . ? O2 C19 O1 124.39(17) . . ? O2 C19 C20 120.49(16) . . ? O1 C19 C20 115.12(17) . . ? C25 C20 C21 118.84(17) . . ? C25 C20 C19 120.22(16) . . ? C21 C20 C19 120.94(17) . . ? C22 C21 C20 120.51(18) . . ? C23 C22 C21 120.08(19) . . ? C22 C23 C24 119.93(18) . . ? C25 C24 C23 119.38(17) . . ? C25 C24 C26 118.78(16) . . ? C23 C24 C26 121.84(16) . . ? C20 C25 C24 121.25(16) . . ? O3 C26 O4 121.17(17) . . ? O3 C26 C24 121.12(17) . . ? O4 C26 C24 117.69(16) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.341 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 930200' ####################################################################### # # 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_lj-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N4 Ni O7' _chemical_formula_weight 565.22 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9566(5) _cell_length_b 18.2591(9) _cell_length_c 15.6736(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.4670(10) _cell_angle_gamma 90.00 _cell_volume 2718.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.826 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13626 _diffrn_reflns_av_R_equivalents 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4787 _reflns_number_gt 4287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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^)+(0.0378P)^2^+1.3559P] 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 4787 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Ni1 Ni -0.05547(2) 0.026341(11) 0.735765(13) 0.02015(8) Uani 1 1 d . . . O1 O -0.22058(11) -0.01953(7) 0.75951(8) 0.0279(3) Uani 1 1 d . . . N1 N -0.10427(15) -0.02458(8) 0.60755(9) 0.0252(3) Uani 1 1 d . . . C1 C -0.01312(18) -0.06274(9) 0.57719(11) 0.0266(4) Uani 1 1 d . . . H1A H 0.0814 -0.0624 0.6107 0.032 Uiso 1 1 calc R . . O1W O -0.11356(14) 0.12553(7) 0.67030(10) 0.0424(3) Uani 1 1 d . . . H1WA H -0.1937 0.1422 0.6406 0.051 Uiso 1 1 d R . . H1WB H -0.0584 0.1472 0.6463 0.051 Uiso 1 1 d R . . O2 O -0.91270(11) -0.06577(7) 0.80117(8) 0.0273(3) Uani 1 1 d . . . N2 N -0.00790(14) 0.08609(8) 0.85751(10) 0.0279(3) Uani 1 1 d . . . C2 C -0.05250(18) -0.10261(9) 0.49862(11) 0.0264(4) Uani 1 1 d . . . H2A H 0.0148 -0.1282 0.4803 0.032 Uiso 1 1 calc R . . O3 O -0.84691(11) 0.03176(6) 0.74160(8) 0.0245(3) Uani 1 1 d . . . N3 N -0.37434(15) -0.16323(8) 0.32858(9) 0.0269(3) Uani 1 1 d . . . H3A H -0.4303 -0.1392 0.3507 0.032 Uiso 1 1 calc R . . C3 C -0.19273(17) -0.10435(9) 0.44719(11) 0.0240(3) Uani 1 1 d . . . O4 O -0.39434(13) 0.05698(7) 0.68971(9) 0.0347(3) Uani 1 1 d . . . N4 N -0.54288(16) -0.28991(8) 0.34114(9) 0.0288(3) Uani 1 1 d . . . H4B H -0.4940 -0.3291 0.3435 0.035 Uiso 1 1 calc R . . C4 C -0.28605(19) -0.06126(11) 0.47585(13) 0.0349(4) Uani 1 1 d . . . H4A H -0.3801 -0.0583 0.4418 0.042 Uiso 1 1 calc R . . O5 O -0.14545(13) -0.18919(7) 0.34359(9) 0.0335(3) Uani 1 1 d . . . C5 C -0.23816(19) -0.02286(11) 0.55510(12) 0.0340(4) Uani 1 1 d . . . H5A H -0.3022 0.0057 0.5730 0.041 Uiso 1 1 calc R . . C6 C -0.23546(17) -0.15524(9) 0.36726(11) 0.0242(4) Uani 1 1 d . . . O6 O -0.6564(2) -0.21788(9) 0.41376(10) 0.0598(5) Uani 1 1 d . . . C7 C -0.43692(18) -0.21018(9) 0.25115(11) 0.0263(4) Uani 1 1 d . . . H7A H -0.3707 -0.2496 0.2499 0.032 Uiso 1 1 calc R . . C8 C -0.4670(2) -0.16596(11) 0.16461(12) 0.0387(5) Uani 1 1 d . . . H8A H -0.3788 -0.1489 0.1574 0.046 Uiso 1 1 calc R . . H8B H -0.5231 -0.1234 0.1686 0.046 Uiso 1 1 calc R . . C9 C -0.5455(3) -0.21151(13) 0.08287(13) 0.0522(6) Uani 1 1 d . . . H9A H -0.5670 -0.1812 0.0296 0.063 Uiso 1 1 calc R . . H9B H -0.4862 -0.2516 0.0753 0.063 Uiso 1 1 calc R . . C10 C -0.6805(2) -0.24169(12) 0.09412(13) 0.0475(6) Uani 1 1 d . . . H10A H -0.7278 -0.2713 0.0424 0.057 Uiso 1 1 calc R . . H10B H -0.7424 -0.2015 0.0974 0.057 Uiso 1 1 calc R . . C11 C -0.6518(2) -0.28798(11) 0.17813(13) 0.0372(4) Uani 1 1 d . . . H11A H -0.5963 -0.3304 0.1727 0.045 Uiso 1 1 calc R . . H11B H -0.7403 -0.3052 0.1847 0.045 Uiso 1 1 calc R . . C12 C -0.57269(18) -0.24397(9) 0.26095(11) 0.0261(4) Uani 1 1 d . . . H12A H -0.6340 -0.2038 0.2678 0.031 Uiso 1 1 calc R . . C13 C -0.58844(19) -0.27340(10) 0.41031(12) 0.0303(4) Uani 1 1 d . . . C15 C 0.0749(2) 0.14555(12) 0.86648(14) 0.0436(5) Uani 1 1 d . . . H15A H 0.1124 0.1571 0.8205 0.052 Uiso 1 1 calc R . . C16 C 0.1068(2) 0.19025(12) 0.94115(14) 0.0438(5) Uani 1 1 d . . . H16A H 0.1639 0.2311 0.9444 0.053 Uiso 1 1 calc R . . C17 C 0.05364(18) 0.17414(10) 1.01100(12) 0.0277(4) Uani 1 1 d . . . C18 C -0.0305(2) 0.11232(10) 1.00259(12) 0.0311(4) Uani 1 1 d . . . H18A H -0.0675 0.0990 1.0482 0.037 Uiso 1 1 calc R . . C19 C -0.05872(19) 0.07058(10) 0.92517(12) 0.0296(4) Uani 1 1 d . . . H19A H -0.1161 0.0296 0.9202 0.036 Uiso 1 1 calc R . . C20 C -0.34764(17) 0.00259(9) 0.73710(11) 0.0237(3) Uani 1 1 d . . . C21 C -0.44510(16) -0.04367(9) 0.77256(11) 0.0246(4) Uani 1 1 d . . . C22 C -0.40134(19) -0.10923(11) 0.81756(15) 0.0395(5) Uani 1 1 d . . . H22A H -0.3097 -0.1256 0.8263 0.047 Uiso 1 1 calc R . . C23 C -0.4931(2) -0.15048(12) 0.84952(17) 0.0480(6) Uani 1 1 d . . . H23A H -0.4632 -0.1946 0.8786 0.058 Uiso 1 1 calc R . . C24 C -0.62934(19) -0.12593(11) 0.83818(14) 0.0364(4) Uani 1 1 d . . . H24A H -0.6906 -0.1535 0.8598 0.044 Uiso 1 1 calc R . . C25 C -0.67379(16) -0.06009(9) 0.79435(11) 0.0229(3) Uani 1 1 d . . . C26 C -0.58184(17) -0.02005(9) 0.76100(11) 0.0222(3) Uani 1 1 d . . . H26A H -0.6126 0.0234 0.7304 0.027 Uiso 1 1 calc R . . C27 C -0.81871(16) -0.02995(9) 0.77952(11) 0.0210(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01312(12) 0.02543(13) 0.02302(12) -0.00142(8) 0.00712(8) -0.00032(8) O1 0.0128(6) 0.0357(7) 0.0367(7) 0.0005(5) 0.0096(5) -0.0009(5) N1 0.0238(7) 0.0281(8) 0.0243(7) 0.0000(6) 0.0081(6) 0.0007(6) C1 0.0206(8) 0.0326(9) 0.0268(9) 0.0004(7) 0.0075(7) -0.0011(7) O1W 0.0346(7) 0.0389(8) 0.0538(9) 0.0136(7) 0.0135(6) 0.0105(6) O2 0.0172(6) 0.0336(7) 0.0337(7) 0.0032(5) 0.0115(5) -0.0035(5) N2 0.0227(7) 0.0326(8) 0.0295(8) -0.0051(6) 0.0096(6) -0.0016(6) C2 0.0250(8) 0.0286(9) 0.0286(9) 0.0003(7) 0.0124(7) 0.0012(7) O3 0.0160(6) 0.0272(6) 0.0317(6) 0.0033(5) 0.0093(5) 0.0013(5) N3 0.0264(7) 0.0287(8) 0.0269(8) -0.0062(6) 0.0099(6) -0.0019(6) C3 0.0262(9) 0.0230(8) 0.0227(8) 0.0014(7) 0.0073(7) 0.0004(7) O4 0.0260(6) 0.0331(7) 0.0506(8) 0.0114(6) 0.0202(6) 0.0049(5) N4 0.0342(8) 0.0233(7) 0.0295(8) 0.0057(6) 0.0105(6) 0.0031(6) C4 0.0237(9) 0.0453(11) 0.0314(10) -0.0084(8) 0.0017(8) 0.0073(8) O5 0.0306(7) 0.0314(7) 0.0398(7) -0.0084(6) 0.0123(6) 0.0032(5) C5 0.0260(9) 0.0429(11) 0.0315(10) -0.0081(8) 0.0060(8) 0.0086(8) C6 0.0269(9) 0.0218(8) 0.0251(8) 0.0030(7) 0.0096(7) 0.0004(7) O6 0.0890(13) 0.0534(10) 0.0461(9) 0.0214(8) 0.0343(9) 0.0414(9) C7 0.0295(9) 0.0249(9) 0.0247(9) -0.0032(7) 0.0083(7) -0.0005(7) C8 0.0555(12) 0.0343(10) 0.0297(10) 0.0006(8) 0.0178(9) -0.0083(9) C9 0.0860(18) 0.0465(13) 0.0232(10) -0.0011(9) 0.0148(11) -0.0036(12) C10 0.0591(14) 0.0420(12) 0.0286(10) -0.0078(9) -0.0065(10) 0.0037(10) C11 0.0377(11) 0.0325(10) 0.0368(11) -0.0044(8) 0.0040(9) -0.0060(8) C12 0.0289(9) 0.0228(8) 0.0260(9) 0.0021(7) 0.0076(7) 0.0008(7) C13 0.0312(9) 0.0290(9) 0.0305(9) 0.0057(7) 0.0088(8) 0.0047(8) C15 0.0446(12) 0.0548(13) 0.0398(11) -0.0151(10) 0.0255(10) -0.0228(10) C16 0.0469(12) 0.0472(12) 0.0434(12) -0.0161(10) 0.0227(10) -0.0244(10) C17 0.0251(8) 0.0294(9) 0.0280(9) -0.0041(7) 0.0072(7) -0.0001(7) C18 0.0394(10) 0.0300(9) 0.0266(9) -0.0017(7) 0.0138(8) -0.0039(8) C19 0.0342(10) 0.0264(9) 0.0292(9) -0.0013(7) 0.0109(8) -0.0041(7) C20 0.0174(8) 0.0277(9) 0.0280(9) -0.0047(7) 0.0100(7) -0.0019(7) C21 0.0160(8) 0.0270(9) 0.0318(9) 0.0005(7) 0.0088(7) -0.0003(6) C22 0.0188(9) 0.0384(11) 0.0633(14) 0.0143(10) 0.0153(9) 0.0087(8) C23 0.0292(10) 0.0390(11) 0.0781(16) 0.0295(11) 0.0196(10) 0.0108(9) C24 0.0250(9) 0.0353(10) 0.0517(12) 0.0161(9) 0.0157(8) -0.0007(8) C25 0.0159(8) 0.0264(9) 0.0260(9) 0.0004(7) 0.0057(7) -0.0019(6) C26 0.0167(8) 0.0223(8) 0.0282(9) 0.0017(7) 0.0076(7) 0.0006(6) C27 0.0154(8) 0.0282(9) 0.0199(8) -0.0026(7) 0.0058(6) -0.0030(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; correla tions 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 Ni1 O1 1.9773(11) . ? Ni1 O3 2.0534(11) 1_655 ? Ni1 O1W 2.0764(13) . ? Ni1 N2 2.1244(14) . ? Ni1 N1 2.1338(14) . ? Ni1 O2 2.2417(12) 1_655 ? Ni1 C27 2.4725(16) 1_655 ? O1 C20 1.273(2) . ? N1 C1 1.340(2) . ? N1 C5 1.340(2) . ? C1 C2 1.382(2) . ? O2 C27 1.2686(19) . ? O2 Ni1 2.2418(12) 1_455 ? N2 C19 1.335(2) . ? N2 C15 1.345(2) . ? C2 C3 1.387(2) . ? O3 C27 1.265(2) . ? O3 Ni1 2.0533(11) 1_455 ? N3 C6 1.341(2) . ? N3 C7 1.464(2) . ? C3 C4 1.391(2) . ? C3 C6 1.515(2) . ? O4 C20 1.244(2) . ? N4 C13 1.329(2) . ? N4 C12 1.465(2) . ? C4 C5 1.381(3) . ? O5 C6 1.235(2) . ? O6 C13 1.229(2) . ? C7 C8 1.529(2) . ? C7 C12 1.535(2) . ? C8 C9 1.531(3) . ? C9 C10 1.510(3) . ? C10 C11 1.518(3) . ? C11 C12 1.529(2) . ? C13 C17 1.517(2) 2_446 ? C15 C16 1.383(3) . ? C16 C17 1.383(3) . ? C17 C18 1.388(2) . ? C17 C13 1.517(2) 2_456 ? C18 C19 1.388(2) . ? C20 C21 1.512(2) . ? C21 C26 1.387(2) . ? C21 C22 1.391(3) . ? C22 C23 1.388(3) . ? C23 C24 1.389(3) . ? C24 C25 1.390(3) . ? C25 C26 1.390(2) . ? C25 C27 1.496(2) . ? C27 Ni1 2.4725(16) 1_455 ? 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 Ni1 O3 154.00(5) . 1_655 ? O1 Ni1 O1W 109.79(5) . . ? O3 Ni1 O1W 96.20(5) 1_655 . ? O1 Ni1 N2 91.28(5) . . ? O3 Ni1 N2 89.16(5) 1_655 . ? O1W Ni1 N2 87.12(6) . . ? O1 Ni1 N1 91.47(5) . . ? O3 Ni1 N1 90.25(5) 1_655 . ? O1W Ni1 N1 87.92(6) . . ? N2 Ni1 N1 174.92(6) . . ? O1 Ni1 O2 92.58(4) . 1_655 ? O3 Ni1 O2 61.43(4) 1_655 1_655 ? O1W Ni1 O2 157.63(5) . 1_655 ? N2 Ni1 O2 91.99(5) . 1_655 ? N1 Ni1 O2 92.16(5) . 1_655 ? O1 Ni1 C27 123.30(5) . 1_655 ? O3 Ni1 C27 30.73(5) 1_655 1_655 ? O1W Ni1 C27 126.91(5) . 1_655 ? N2 Ni1 C27 91.57(5) . 1_655 ? N1 Ni1 C27 90.50(5) . 1_655 ? O2 Ni1 C27 30.73(5) 1_655 1_655 ? C20 O1 Ni1 128.84(11) . . ? C1 N1 C5 116.71(15) . . ? C1 N1 Ni1 125.03(11) . . ? C5 N1 Ni1 118.10(12) . . ? N1 C1 C2 123.31(16) . . ? C27 O2 Ni1 84.74(9) . 1_455 ? C19 N2 C15 117.05(16) . . ? C19 N2 Ni1 124.67(12) . . ? C15 N2 Ni1 118.23(12) . . ? C1 C2 C3 119.77(16) . . ? C27 O3 Ni1 93.26(9) . 1_455 ? C6 N3 C7 124.28(14) . . ? C2 C3 C4 116.92(15) . . ? C2 C3 C6 118.59(15) . . ? C4 C3 C6 124.41(15) . . ? C13 N4 C12 122.60(15) . . ? C5 C4 C3 119.60(16) . . ? N1 C5 C4 123.46(16) . . ? O5 C6 N3 123.55(16) . . ? O5 C6 C3 120.50(15) . . ? N3 C6 C3 115.86(14) . . ? N3 C7 C8 110.35(14) . . ? N3 C7 C12 108.72(13) . . ? C8 C7 C12 110.91(14) . . ? C7 C8 C9 111.75(16) . . ? C10 C9 C8 110.43(18) . . ? C9 C10 C11 111.23(17) . . ? C10 C11 C12 111.02(15) . . ? N4 C12 C11 110.33(14) . . ? N4 C12 C7 110.99(13) . . ? C11 C12 C7 111.77(15) . . ? O6 C13 N4 123.38(17) . . ? O6 C13 C17 118.64(16) . 2_446 ? N4 C13 C17 117.98(15) . 2_446 ? N2 C15 C16 122.85(18) . . ? C17 C16 C15 119.95(18) . . ? C16 C17 C18 117.46(17) . . ? C16 C17 C13 117.45(16) . 2_456 ? C18 C17 C13 125.07(16) . 2_456 ? C17 C18 C19 119.16(17) . . ? N2 C19 C18 123.52(17) . . ? O4 C20 O1 125.50(15) . . ? O4 C20 C21 119.95(14) . . ? O1 C20 C21 114.55(15) . . ? C26 C21 C22 118.64(16) . . ? C26 C21 C20 119.42(15) . . ? C22 C21 C20 121.93(15) . . ? C23 C22 C21 120.65(16) . . ? C22 C23 C24 120.14(18) . . ? C23 C24 C25 119.77(17) . . ? C24 C25 C26 119.53(15) . . ? C24 C25 C27 122.98(15) . . ? C26 C25 C27 117.48(15) . . ? C21 C26 C25 121.24(15) . . ? O3 C27 O2 120.48(14) . . ? O3 C27 C25 117.92(14) . . ? O2 C27 C25 121.56(15) . . ? O3 C27 Ni1 56.01(8) . 1_455 ? O2 C27 Ni1 64.54(8) . 1_455 ? C25 C27 Ni1 172.29(12) . 1_455 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.527 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 930201' ####################################################################### # # 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_lj-6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N4 O7 Zn' _chemical_formula_weight 571.88 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7361(6) _cell_length_b 18.0736(12) _cell_length_c 16.1041(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.9560(10) _cell_angle_gamma 90.00 _cell_volume 2724.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13743 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4803 _reflns_number_gt 4083 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _refine_special_details ; Refinemen t 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^)+(0.0341P)^2^+1.1805P]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 4803 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Zn1 Zn 0.43260(2) 0.036840(13) 0.229383(15) 0.02575(8) Uani 1 1 d . . . O1 O 0.28875(14) -0.02051(8) 0.26507(10) 0.0338(3) Uani 1 1 d . . . N1 N 0.38072(19) -0.01725(10) 0.09973(11) 0.0326(4) Uani 1 1 d . . . C1 C 0.2501(2) -0.01209(14) 0.04626(15) 0.0448(6) Uani 1 1 d . . . H1A H 0.1859 0.0201 0.0607 0.054 Uiso 1 1 calc R . . O1W O 0.39683(16) 0.13671(8) 0.16781(10) 0.0422(4) Uani 1 1 d . . . H1WA H 0.4574 0.1595 0.1481 0.051 Uiso 1 1 d R . . H1WB H 0.3193 0.1576 0.1406 0.051 Uiso 1 1 d R . . O2 O -0.36165(14) 0.01612(8) 0.24562(9) 0.0305(3) Uani 1 1 d . . . N2 N 0.01475(19) -0.39936(10) 0.14736(12) 0.0366(4) Uani 1 1 d . . . C2 C 0.2041(2) -0.05190(14) -0.02967(15) 0.0429(6) Uani 1 1 d . . . H2A H 0.1113 -0.0465 -0.0647 0.051 Uiso 1 1 calc R . . O3 O 0.10987(16) 0.05072(8) 0.19159(10) 0.0377(4) Uani 1 1 d . . . N3 N 0.11950(17) -0.15782(9) -0.16905(10) 0.0282(4) Uani 1 1 d . . . H3A H 0.0610 -0.1307 -0.1510 0.034 Uiso 1 1 calc R . . C3 C 0.2980(2) -0.09987(11) -0.05293(12) 0.0266(4) Uani 1 1 d . . . N4 N -0.04808(18) -0.28510(9) -0.15076(11) 0.0300(4) Uani 1 1 d . . . H4B H -0.0009 -0.3257 -0.1482 0.036 Uiso 1 1 calc R . . O4 O -0.40502(16) -0.08004(9) 0.31981(11) 0.0446(4) Uani 1 1 d . . . C4 C 0.4362(2) -0.10202(11) 0.00023(13) 0.0296(5) Uani 1 1 d . . . H4A H 0.5044 -0.1314 -0.0145 0.036 Uiso 1 1 calc R . . O5 O 0.35039(15) -0.18860(8) -0.14980(10) 0.0381(4) Uani 1 1 d . . . C5 C 0.4728(2) -0.06083(12) 0.07478(13) 0.0312(5) Uani 1 1 d . . . H5A H 0.5663 -0.0634 0.1096 0.037 Uiso 1 1 calc R . . O6 O -0.15607(19) -0.20760(9) -0.07875(10) 0.0505(5) Uani 1 1 d . . . C6 C 0.2578(2) -0.15161(11) -0.12927(13) 0.0264(4) Uani 1 1 d . . . C7 C 0.0602(2) -0.20770(11) -0.24154(12) 0.0283(4) Uani 1 1 d . . . H7A H 0.1291 -0.2475 -0.2404 0.034 Uiso 1 1 calc R . . C8 C 0.0331(3) -0.16680(13) -0.32726(14) 0.0425(6) Uani 1 1 d . . . H8A H -0.0272 -0.1242 -0.3267 0.051 Uiso 1 1 calc R . . H8B H 0.1232 -0.1491 -0.3344 0.051 Uiso 1 1 calc R . . C9 C -0.0387(3) -0.21657(15) -0.40293(15) 0.0524(7) Uani 1 1 d . . . H9A H -0.0584 -0.1885 -0.4562 0.063 Uiso 1 1 calc R . . H9B H 0.0249 -0.2569 -0.4068 0.063 Uiso 1 1 calc R . . C10 C -0.1769(3) -0.24747(14) -0.39142(15) 0.0475(6) Uani 1 1 d . . . H10A H -0.2428 -0.2072 -0.3918 0.057 Uiso 1 1 calc R . . H10B H -0.2201 -0.2800 -0.4394 0.057 Uiso 1 1 calc R . . C11 C -0.1514(3) -0.28986(12) -0.30774(14) 0.0394(5) Uani 1 1 d . . . H11A H -0.0926 -0.3328 -0.3097 0.047 Uiso 1 1 calc R . . H11B H -0.2421 -0.3071 -0.3011 0.047 Uiso 1 1 calc R . . C12 C -0.0777(2) -0.24191(11) -0.23036(13) 0.0265(4) Uani 1 1 d . . . H12A H -0.1427 -0.2016 -0.2261 0.032 Uiso 1 1 calc R . . C13 C -0.0899(2) -0.26520(11) -0.08222(13) 0.0301(5) Uani 1 1 d . . . C14 C -0.0524(2) -0.31541(12) -0.00431(13) 0.0306(5) Uani 1 1 d . . . C15 C 0.0215(3) -0.38101(12) 0.00143(14) 0.0383(5) Uani 1 1 d . . . H15A H 0.0500 -0.3986 -0.0456 0.046 Uiso 1 1 calc R . . C16 C 0.0531(3) -0.42061(12) 0.07812(14) 0.0385(5) Uani 1 1 d . . . H16A H 0.1039 -0.4646 0.0812 0.046 Uiso 1 1 calc R . . C17 C -0.0588(3) -0.33642(16) 0.14079(17) 0.0596(8) Uani 1 1 d . . . H17A H -0.0878 -0.3206 0.1883 0.072 Uiso 1 1 calc R . . C18 C -0.0940(3) -0.29352(16) 0.06712(16) 0.0568(8) Uani 1 1 d . . . H18A H -0.1457 -0.2500 0.0656 0.068 Uiso 1 1 calc R . . C19 C 0.1578(2) -0.00104(11) 0.24181(13) 0.0263(4) Uani 1 1 d . . . C20 C 0.0606(2) -0.04612(11) 0.28030(13) 0.0278(4) Uani 1 1 d . . . C21 C 0.1123(2) -0.10717(13) 0.33130(17) 0.0457(6) Uani 1 1 d . . . H21A H 0.2078 -0.1205 0.3418 0.055 Uiso 1 1 calc R . . C22 C 0.0227(3) -0.14856(15) 0.3668(2) 0.0586(8) Uani 1 1 d . . . H22A H 0.0577 -0.1903 0.3997 0.070 Uiso 1 1 calc R . . C23 C -0.1180(2) -0.12813(13) 0.35362(17) 0.0455(6) Uani 1 1 d . . . H23A H -0.1777 -0.1558 0.3779 0.055 Uiso 1 1 calc R . . C24 C -0.1708(2) -0.06607(11) 0.30392(13) 0.0266(4) Uani 1 1 d . . . C25 C -0.0815(2) -0.02628(10) 0.26662(13) 0.0249(4) Uani 1 1 d . . . H25A H -0.1174 0.0143 0.2319 0.030 Uiso 1 1 calc R . . C26 C -0.3233(2) -0.04246(11) 0.28991(13) 0.0263(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01666(13) 0.03336(14) 0.02786(14) -0.00160(10) 0.00720(9) -0.00008(9) O1 0.0168(7) 0.0445(9) 0.0420(9) 0.0003(7) 0.0112(6) -0.0020(6) N1 0.0301(10) 0.0399(10) 0.0277(9) -0.0038(8) 0.0077(8) -0.0001(8) C1 0.0314(13) 0.0603(16) 0.0400(13) -0.0171(12) 0.0056(10) 0.0107(11) O1W 0.0318(9) 0.0408(9) 0.0539(10) 0.0148(8) 0.0116(7) 0.0050(7) O2 0.0186(7) 0.0386(8) 0.0343(8) 0.0031(7) 0.0074(6) 0.0028(6) N2 0.0319(10) 0.0455(11) 0.0339(10) 0.0085(9) 0.0115(8) 0.0051(8) C2 0.0279(12) 0.0593(15) 0.0373(13) -0.0141(11) 0.0019(10) 0.0074(11) O3 0.0307(8) 0.0375(9) 0.0500(10) 0.0100(7) 0.0197(7) 0.0050(6) N3 0.0255(9) 0.0303(9) 0.0303(9) -0.0074(7) 0.0104(7) 0.0005(7) C3 0.0280(11) 0.0267(10) 0.0262(11) 0.0016(8) 0.0091(9) -0.0009(8) N4 0.0323(10) 0.0267(9) 0.0318(10) 0.0046(7) 0.0100(8) 0.0035(7) O4 0.0250(8) 0.0507(10) 0.0638(11) 0.0101(8) 0.0219(8) -0.0053(7) C4 0.0280(11) 0.0309(11) 0.0314(11) 0.0004(9) 0.0106(9) 0.0021(8) O5 0.0267(8) 0.0381(8) 0.0510(10) -0.0124(7) 0.0129(7) 0.0017(6) C5 0.0265(11) 0.0378(12) 0.0287(11) 0.0011(9) 0.0065(9) -0.0015(9) O6 0.0631(12) 0.0526(10) 0.0369(9) 0.0098(8) 0.0155(8) 0.0304(9) C6 0.0272(11) 0.0253(10) 0.0279(11) 0.0023(8) 0.0096(9) -0.0012(8) C7 0.0304(12) 0.0280(11) 0.0283(11) -0.0060(8) 0.0112(9) -0.0009(8) C8 0.0580(16) 0.0418(13) 0.0325(12) -0.0002(10) 0.0205(11) -0.0087(11) C9 0.080(2) 0.0513(15) 0.0269(13) -0.0039(11) 0.0160(13) -0.0018(14) C10 0.0561(17) 0.0482(14) 0.0292(13) -0.0079(11) -0.0035(11) 0.0045(12) C11 0.0376(13) 0.0365(12) 0.0398(13) -0.0066(10) 0.0038(10) -0.0078(10) C12 0.0275(11) 0.0261(10) 0.0254(11) 0.0015(8) 0.0062(8) 0.0012(8) C13 0.0253(11) 0.0328(11) 0.0306(12) 0.0025(9) 0.0051(9) 0.0023(9) C14 0.0248(11) 0.0361(12) 0.0301(11) 0.0037(9) 0.0065(9) 0.0005(9) C15 0.0530(15) 0.0334(12) 0.0299(12) 0.0000(10) 0.0137(10) 0.0054(10) C16 0.0511(15) 0.0293(12) 0.0347(13) 0.0023(10) 0.0112(11) 0.0053(10) C17 0.0656(19) 0.082(2) 0.0412(15) 0.0194(14) 0.0308(14) 0.0401(16) C18 0.0659(18) 0.0678(18) 0.0433(15) 0.0194(13) 0.0260(13) 0.0426(15) C19 0.0205(10) 0.0285(10) 0.0324(11) -0.0063(9) 0.0113(9) -0.0027(8) C20 0.0192(10) 0.0307(11) 0.0343(12) 0.0003(9) 0.0086(9) 0.0010(8) C21 0.0247(12) 0.0473(14) 0.0674(17) 0.0206(12) 0.0163(11) 0.0118(10) C22 0.0360(14) 0.0522(15) 0.090(2) 0.0409(15) 0.0209(14) 0.0161(12) C23 0.0320(13) 0.0451(14) 0.0642(16) 0.0232(12) 0.0215(12) 0.0024(10) C24 0.0192(10) 0.0289(10) 0.0322(11) 0.0021(9) 0.0079(8) 0.0002(8) C25 0.0215(10) 0.0244(10) 0.0284(11) 0.0024(8) 0.0064(8) 0.0016(8) C26 0.0195(10) 0.0335(11) 0.0257(10) -0.0053(9) 0.0057(8) -0.0028(8) _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 Zn1 O1 1.9515(14) . ? Zn1 O2 1.9833(13) 1_655 ? Zn1 O1W 2.0428(15) . ? Zn1 N2 2.2301(18) 2 ? Zn1 N1 2.2340(17) . ? O1 C19 1.275(2) . ? N1 C1 1.329(3) . ? N1 C5 1.335(3) . ? C1 C2 1.383(3) . ? O2 C26 1.274(2) . ? O2 Zn1 1.9833(13) 1_455 ? N2 C16 1.326(3) . ? N2 C17 1.332(3) . ? N2 Zn1 2.2300(18) 2_545 ? C2 C3 1.384(3) . ? O3 C19 1.241(2) . ? N3 C6 1.327(3) . ? N3 C7 1.462(2) . ? C3 C4 1.382(3) . ? C3 C6 1.508(3) . ? N4 C13 1.327(3) . ? N4 C12 1.460(2) . ? O4 C26 1.240(2) . ? C4 C5 1.374(3) . ? O5 C6 1.238(2) . ? O6 C13 1.234(2) . ? C7 C8 1.524(3) . ? C7 C12 1.532(3) . ? C8 C9 1.521(3) . ? C9 C10 1.514(4) . ? C10 C11 1.510(3) . ? C11 C12 1.526(3) . ? C13 C14 1.510(3) . ? C14 C15 1.377(3) . ? C14 C18 1.379(3) . ? C15 C16 1.387(3) . ? C17 C18 1.379(3) . ? C19 C20 1.506(3) . ? C20 C21 1.385(3) . ? C20 C25 1.387(3) . ? C21 C22 1.386(3) . ? C22 C23 1.378(3) . ? C23 C24 1.391(3) . ? C24 C25 1.386(3) . ? C24 C26 1.502(3) . ? 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 Zn1 O2 129.90(6) . 1_655 ? O1 Zn1 O1W 124.88(6) . . ? O2 Zn1 O1W 105.19(6) 1_655 . ? O1 Zn1 N2 91.18(6) . 2 ? O2 Zn1 N2 90.20(6) 1_655 2 ? O1W Zn1 N2 86.67(7) . 2 ? O1 Zn1 N1 92.67(6) . . ? O2 Zn1 N1 90.08(6) 1_655 . ? O1W Zn1 N1 88.19(6) . . ? N2 Zn1 N1 174.74(7) 2 . ? C19 O1 Zn1 120.48(13) . . ? C1 N1 C5 116.64(18) . . ? C1 N1 Zn1 120.35(14) . . ? C5 N1 Zn1 122.77(14) . . ? N1 C1 C2 123.8(2) . . ? C26 O2 Zn1 111.14(12) . 1_455 ? C16 N2 C17 116.71(19) . . ? C16 N2 Zn1 123.34(15) . 2_545 ? C17 N2 Zn1 119.94(15) . 2_545 ? C1 C2 C3 119.2(2) . . ? C6 N3 C7 124.27(16) . . ? C4 C3 C2 116.90(19) . . ? C4 C3 C6 118.54(18) . . ? C2 C3 C6 124.49(18) . . ? C13 N4 C12 123.62(17) . . ? C5 C4 C3 120.04(19) . . ? N1 C5 C4 123.24(19) . . ? O5 C6 N3 122.81(18) . . ? O5 C6 C3 120.51(18) . . ? N3 C6 C3 116.58(17) . . ? N3 C7 C8 110.87(16) . . ? N3 C7 C12 108.75(15) . . ? C8 C7 C12 111.30(17) . . ? C9 C8 C7 111.46(18) . . ? C10 C9 C8 110.4(2) . . ? C11 C10 C9 111.3(2) . . ? C10 C11 C12 111.45(18) . . ? N4 C12 C11 110.38(16) . . ? N4 C12 C7 110.55(16) . . ? C11 C12 C7 111.35(17) . . ? O6 C13 N4 123.37(19) . . ? O6 C13 C14 118.66(19) . . ? N4 C13 C14 117.97(18) . . ? C15 C14 C18 117.4(2) . . ? C15 C14 C13 125.17(19) . . ? C18 C14 C13 117.48(19) . . ? C14 C15 C16 119.2(2) . . ? N2 C16 C15 123.7(2) . . ? N2 C17 C18 123.3(2) . . ? C14 C18 C17 119.7(2) . . ? O3 C19 O1 124.48(18) . . ? O3 C19 C20 120.65(17) . . ? O1 C19 C20 114.87(18) . . ? C21 C20 C25 118.96(18) . . ? C21 C20 C19 120.55(18) . . ? C25 C20 C19 120.48(18) . . ? C20 C21 C22 120.5(2) . . ? C23 C22 C21 120.2(2) . . ? C22 C23 C24 119.9(2) . . ? C25 C24 C23 119.43(18) . . ? C25 C24 C26 119.98(18) . . ? C23 C24 C26 120.59(18) . . ? C24 C25 C20 120.93(18) . . ? O4 C26 O2 123.54(18) . . ? O4 C26 C24 119.98(18) . . ? O2 C26 C24 116.47(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.331 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 930202' ####################################################################### # # 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_lj-8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 Cd N4 O7' _chemical_formula_weight 618.91 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' Cd Cd -0.8075 1.2024 '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 10.1518(6) _cell_length_b 11.2296(7) _cell_length_c 12.6969(7) _cell_angle_alpha 86.4710(10) _cell_angle_beta 79.7310(10) _cell_angle_gamma 66.1370(10) _cell_volume 1302.43(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.63 _cell_measurement_theta_max 25.00 _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 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.852 _exptl_absorpt_correction_T_max 0.891 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6635 _diffrn_reflns_av_R_equivalents 0.0114 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4547 _reflns_number_gt 4249 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _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 abou t 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^)+(0.0267P)^2^+0.8345P] 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 4547 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0572 _refine_ls_wR_factor_gt 0.0561 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.002 _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 Cd1 Cd 0.082781(17) 0.123122(15) 0.046821(12) 0.02414(6) Uani 1 1 d . . . N1 N 0.0862(2) 0.01310(18) 0.20928(14) 0.0275(4) Uani 1 1 d . . . O1 O -0.11003(18) 0.24448(17) -0.03548(15) 0.0415(4) Uani 1 1 d . . . C1 C -0.0127(3) -0.0362(2) 0.24765(19) 0.0320(5) Uani 1 1 d . . . H1A H -0.0891 -0.0209 0.2106 0.038 Uiso 1 1 calc R . . O1W O -0.7014(2) 0.16043(18) -0.31763(15) 0.0451(4) Uani 1 1 d . . . H1WA H -0.7117 0.1589 -0.2497 0.054 Uiso 1 1 d R . . H1WB H -0.6131 0.1082 -0.3374 0.054 Uiso 1 1 d R . . O2 O -0.76938(18) 0.18393(18) -0.09213(14) 0.0399(4) Uani 1 1 d . . . N2 N 1.0054(2) -0.67864(19) 0.15174(16) 0.0340(5) Uani 1 1 d . . . C2 C -0.0061(3) -0.1087(3) 0.3398(2) 0.0407(6) Uani 1 1 d . . . H2A H -0.0783 -0.1394 0.3651 0.049 Uiso 1 1 calc R . . O3 O -0.67958(18) 0.12207(17) 0.05724(14) 0.0365(4) Uani 1 1 d . . . N3 N 0.3886(2) -0.2099(2) 0.47002(15) 0.0322(4) Uani 1 1 d . . . H3B H 0.3613 -0.2721 0.4643 0.039 Uiso 1 1 calc R . . C3 C 0.1089(3) -0.1352(3) 0.3937(2) 0.0384(6) Uani 1 1 d . . . H3A H 0.1161 -0.1852 0.4553 0.046 Uiso 1 1 calc R . . O4 O -0.15899(17) 0.08174(15) 0.03941(12) 0.0305(4) Uani 1 1 d . . . N4 N 0.6975(2) -0.39286(19) 0.44149(16) 0.0350(5) Uani 1 1 d . . . H4A H 0.7044 -0.3316 0.3997 0.042 Uiso 1 1 calc R . . C4 C 0.2142(2) -0.0862(2) 0.35483(18) 0.0288(5) Uani 1 1 d . . . O5 O 0.3964(2) -0.02441(19) 0.39599(16) 0.0475(5) Uani 1 1 d . . . C5 C 0.1970(2) -0.0115(2) 0.26331(18) 0.0288(5) Uani 1 1 d . . . H5A H 0.2654 0.0233 0.2379 0.035 Uiso 1 1 calc R . . O6 O 0.7572(2) -0.60910(17) 0.45789(15) 0.0496(5) Uani 1 1 d . . . C6 C 0.3414(3) -0.1048(2) 0.40909(18) 0.0319(5) Uani 1 1 d . . . C7 C 0.4859(3) -0.2218(2) 0.54660(18) 0.0301(5) Uani 1 1 d . . . H7A H 0.5329 -0.1609 0.5263 0.036 Uiso 1 1 calc R . . C8 C 0.3947(3) -0.1841(3) 0.6577(2) 0.0419(6) Uani 1 1 d . . . H8A H 0.3433 -0.2407 0.6767 0.050 Uiso 1 1 calc R . . H8B H 0.3223 -0.0955 0.6563 0.050 Uiso 1 1 calc R . . C9 C 0.4872(3) -0.1936(3) 0.7425(2) 0.0499(7) Uani 1 1 d . . . H9A H 0.5299 -0.1298 0.7284 0.060 Uiso 1 1 calc R . . H9B H 0.4256 -0.1741 0.8124 0.060 Uiso 1 1 calc R . . C10 C 0.6063(4) -0.3269(3) 0.7431(2) 0.0589(9) Uani 1 1 d . . . H10A H 0.5635 -0.3890 0.7673 0.071 Uiso 1 1 calc R . . H10B H 0.6688 -0.3281 0.7930 0.071 Uiso 1 1 calc R . . C11 C 0.6977(3) -0.3676(3) 0.6327(2) 0.0518(8) Uani 1 1 d . . . H11A H 0.7687 -0.4566 0.6352 0.062 Uiso 1 1 calc R . . H11B H 0.7508 -0.3125 0.6127 0.062 Uiso 1 1 calc R . . C12 C 0.6040(3) -0.3580(2) 0.54709(18) 0.0344(5) Uani 1 1 d . . . H12A H 0.5574 -0.4197 0.5644 0.041 Uiso 1 1 calc R . . C13 C 0.7717(3) -0.5156(2) 0.4084(2) 0.0337(5) Uani 1 1 d . . . C14 C 0.8765(2) -0.5376(2) 0.30407(19) 0.0304(5) Uani 1 1 d . . . C15 C 0.9165(3) -0.6510(2) 0.2463(2) 0.0340(5) Uani 1 1 d . . . H15A H 0.8793 -0.7115 0.2750 0.041 Uiso 1 1 calc R . . C16 C 0.9362(3) -0.4497(2) 0.2621(2) 0.0352(6) Uani 1 1 d . . . H16A H 0.9150 -0.3739 0.2997 0.042 Uiso 1 1 calc R . . C17 C 1.0271(3) -0.4760(2) 0.1643(2) 0.0391(6) Uani 1 1 d . . . H17A H 1.0673 -0.4179 0.1344 0.047 Uiso 1 1 calc R . . C18 C 1.0572(3) -0.5899(2) 0.1119(2) 0.0379(6) Uani 1 1 d . . . H18A H 1.1169 -0.6062 0.0452 0.046 Uiso 1 1 calc R . . C19 C -0.1918(2) 0.1841(2) -0.01584(18) 0.0281(5) Uani 1 1 d . . . C20 C -0.3312(2) 0.2341(2) -0.06127(19) 0.0292(5) Uani 1 1 d . . . C21 C -0.3537(3) 0.3276(3) -0.1409(3) 0.0511(8) Uani 1 1 d . . . H21A H -0.2856 0.3638 -0.1626 0.061 Uiso 1 1 calc R . . C22 C -0.4776(4) 0.3667(3) -0.1879(3) 0.0660(10) Uani 1 1 d . . . H22A H -0.4916 0.4278 -0.2423 0.079 Uiso 1 1 calc R . . C23 C -0.5809(3) 0.3150(3) -0.1538(3) 0.0538(8) Uani 1 1 d . . . H23A H -0.6642 0.3419 -0.1852 0.065 Uiso 1 1 calc R . . C24 C -0.5608(2) 0.2233(2) -0.07304(19) 0.0304(5) Uani 1 1 d . . . C25 C -0.6752(2) 0.1712(2) -0.03339(19) 0.0298(5) Uani 1 1 d . . . C26 C -0.4344(2) 0.1819(2) -0.02864(17) 0.0240(5) Uani 1 1 d . . . H26A H -0.4187 0.1184 0.0237 0.029 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 Cd1 0.02028(9) 0.02872(10) 0.02580(10) 0.00441(6) -0.00648(6) -0.01174(7) N1 0.0241(10) 0.0327(10) 0.0264(10) 0.0033(8) -0.0063(8) -0.0117(9) O1 0.0292(9) 0.0464(11) 0.0610(12) 0.0136(9) -0.0207(8) -0.0239(9) C1 0.0246(12) 0.0414(14) 0.0321(12) 0.0046(10) -0.0086(10) -0.0144(11) O1W 0.0386(10) 0.0449(11) 0.0499(11) 0.0041(9) -0.0082(9) -0.0148(9) O2 0.0259(9) 0.0576(12) 0.0462(10) 0.0087(9) -0.0110(8) -0.0259(9) N2 0.0316(11) 0.0314(11) 0.0366(11) -0.0010(9) -0.0021(9) -0.0113(9) C2 0.0305(13) 0.0544(17) 0.0452(15) 0.0188(13) -0.0106(11) -0.0260(13) O3 0.0299(9) 0.0417(10) 0.0389(10) 0.0064(8) -0.0034(7) -0.0173(8) N3 0.0312(11) 0.0370(11) 0.0322(11) 0.0063(9) -0.0123(9) -0.0155(9) C3 0.0352(14) 0.0488(15) 0.0364(14) 0.0192(12) -0.0125(11) -0.0219(12) O4 0.0259(8) 0.0321(9) 0.0309(9) 0.0036(7) -0.0108(7) -0.0069(7) N4 0.0355(12) 0.0288(11) 0.0341(11) 0.0028(9) -0.0031(9) -0.0077(9) C4 0.0256(12) 0.0357(13) 0.0262(12) 0.0062(10) -0.0065(9) -0.0133(10) O5 0.0459(11) 0.0546(12) 0.0590(12) 0.0240(10) -0.0265(9) -0.0336(10) C5 0.0259(12) 0.0356(13) 0.0275(12) 0.0049(10) -0.0053(9) -0.0152(10) O6 0.0587(13) 0.0334(10) 0.0509(11) 0.0072(9) 0.0029(9) -0.0184(9) C6 0.0264(12) 0.0408(14) 0.0286(12) 0.0072(10) -0.0075(10) -0.0134(11) C7 0.0291(12) 0.0352(13) 0.0266(12) 0.0043(10) -0.0085(10) -0.0125(11) C8 0.0367(15) 0.0504(16) 0.0315(13) -0.0008(12) -0.0002(11) -0.0124(13) C9 0.0636(19) 0.0594(18) 0.0280(14) -0.0013(12) -0.0079(13) -0.0255(16) C10 0.082(2) 0.0599(19) 0.0392(16) 0.0092(14) -0.0321(16) -0.0247(18) C11 0.0467(17) 0.0520(17) 0.0489(17) 0.0036(14) -0.0268(14) -0.0043(14) C12 0.0356(14) 0.0340(13) 0.0310(13) 0.0021(10) -0.0079(11) -0.0105(11) C13 0.0302(13) 0.0311(13) 0.0380(13) 0.0004(11) -0.0072(10) -0.0100(11) C14 0.0250(12) 0.0273(12) 0.0366(13) 0.0009(10) -0.0073(10) -0.0071(10) C15 0.0322(13) 0.0286(13) 0.0419(14) 0.0033(10) -0.0045(11) -0.0140(11) C16 0.0318(13) 0.0251(12) 0.0487(15) 0.0002(11) -0.0097(11) -0.0102(11) C17 0.0325(14) 0.0293(13) 0.0538(16) 0.0068(11) -0.0026(12) -0.0133(11) C18 0.0329(14) 0.0374(14) 0.0382(14) 0.0061(11) -0.0011(11) -0.0115(12) C19 0.0221(12) 0.0317(13) 0.0292(12) -0.0026(10) -0.0059(9) -0.0085(10) C20 0.0238(12) 0.0302(12) 0.0383(13) 0.0073(10) -0.0131(10) -0.0133(10) C21 0.0438(16) 0.0558(18) 0.073(2) 0.0328(16) -0.0305(15) -0.0357(15) C22 0.060(2) 0.069(2) 0.097(3) 0.058(2) -0.0502(19) -0.0463(18) C23 0.0409(16) 0.0584(18) 0.080(2) 0.0367(16) -0.0395(16) -0.0311(15) C24 0.0229(12) 0.0332(13) 0.0387(13) 0.0079(10) -0.0097(10) -0.0139(10) C25 0.0198(11) 0.0265(12) 0.0412(14) -0.0005(10) -0.0028(10) -0.0082(10) C26 0.0206(11) 0.0257(11) 0.0249(11) 0.0031(9) -0.0038(9) -0.0088(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 Cd1 O1 2.2752(16) . ? Cd1 N1 2.3365(18) . ? Cd1 O2 2.3597(17) 1_655 ? Cd1 O4 2.3786(16) 2 ? Cd1 N2 2.434(2) 1_465 ? Cd1 O3 2.4348(16) 1_655 ? Cd1 C25 2.734(2) 1_655 ? N1 C1 1.340(3) . ? N1 C5 1.346(3) . ? O1 C19 1.254(3) . ? C1 C2 1.379(3) . ? O2 C25 1.273(3) . ? O2 Cd1 2.3597(17) 1_455 ? N2 C15 1.336(3) . ? N2 C18 1.340(3) . ? N2 Cd1 2.434(2) 1_645 ? C2 C3 1.378(3) . ? O3 C25 1.247(3) . ? O3 Cd1 2.4349(16) 1_455 ? N3 C6 1.335(3) . ? N3 C7 1.470(3) . ? C3 C4 1.394(3) . ? O4 C19 1.264(3) . ? O4 Cd1 2.3787(16) 2 ? N4 C13 1.328(3) . ? N4 C12 1.471(3) . ? C4 C5 1.385(3) . ? C4 C6 1.505(3) . ? O5 C6 1.230(3) . ? O6 C13 1.237(3) . ? C7 C12 1.515(3) . ? C7 C8 1.522(3) . ? C8 C9 1.523(4) . ? C9 C10 1.497(4) . ? C10 C11 1.518(4) . ? C11 C12 1.540(3) . ? C13 C14 1.508(3) . ? C14 C15 1.384(3) . ? C14 C16 1.389(3) . ? C16 C17 1.377(4) . ? C17 C18 1.374(4) . ? C19 C20 1.502(3) . ? C20 C26 1.387(3) . ? C20 C21 1.391(3) . ? C21 C22 1.385(4) . ? C22 C23 1.387(4) . ? C23 C24 1.388(3) . ? C24 C26 1.387(3) . ? C24 C25 1.500(3) . ? C25 Cd1 2.734(2) 1_455 ? 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 Cd1 N1 129.54(6) . . ? O1 Cd1 O2 87.15(6) . 1_655 ? N1 Cd1 O2 143.09(6) . 1_655 ? O1 Cd1 O4 100.25(6) . 2 ? N1 Cd1 O4 87.31(6) . 2 ? O2 Cd1 O4 89.94(6) 1_655 2 ? O1 Cd1 N2 83.43(7) . 1_465 ? N1 Cd1 N2 87.03(7) . 1_465 ? O2 Cd1 N2 94.56(7) 1_655 1_465 ? O4 Cd1 N2 174.34(6) 2 1_465 ? O1 Cd1 O3 136.54(6) . 1_655 ? N1 Cd1 O3 89.57(6) . 1_655 ? O2 Cd1 O3 54.68(6) 1_655 1_655 ? O4 Cd1 O3 99.65(6) 2 1_655 ? N2 Cd1 O3 80.27(6) 1_465 1_655 ? O1 Cd1 C25 111.74(7) . 1_655 ? N1 Cd1 C25 116.58(7) . 1_655 ? O2 Cd1 C25 27.71(6) 1_655 1_655 ? O4 Cd1 C25 97.56(6) 2 1_655 ? N2 Cd1 C25 84.95(7) 1_465 1_655 ? O3 Cd1 C25 27.12(6) 1_655 1_655 ? C1 N1 C5 117.69(19) . . ? C1 N1 Cd1 122.33(14) . . ? C5 N1 Cd1 119.77(15) . . ? C19 O1 Cd1 103.21(14) . . ? N1 C1 C2 122.8(2) . . ? C25 O2 Cd1 92.75(14) . 1_455 ? C15 N2 C18 117.0(2) . . ? C15 N2 Cd1 125.64(16) . 1_645 ? C18 N2 Cd1 117.35(16) . 1_645 ? C3 C2 C1 119.1(2) . . ? C25 O3 Cd1 89.95(13) . 1_455 ? C6 N3 C7 121.6(2) . . ? C2 C3 C4 119.2(2) . . ? C19 O4 Cd1 119.34(14) . 2 ? C13 N4 C12 122.2(2) . . ? C5 C4 C3 117.8(2) . . ? C5 C4 C6 118.3(2) . . ? C3 C4 C6 123.9(2) . . ? N1 C5 C4 123.3(2) . . ? O5 C6 N3 123.2(2) . . ? O5 C6 C4 119.6(2) . . ? N3 C6 C4 117.2(2) . . ? N3 C7 C12 112.1(2) . . ? N3 C7 C8 108.8(2) . . ? C12 C7 C8 110.4(2) . . ? C7 C8 C9 112.4(2) . . ? C10 C9 C8 111.0(2) . . ? C9 C10 C11 111.7(2) . . ? C10 C11 C12 112.3(2) . . ? N4 C12 C7 110.80(19) . . ? N4 C12 C11 109.7(2) . . ? C7 C12 C11 110.1(2) . . ? O6 C13 N4 123.4(2) . . ? O6 C13 C14 120.2(2) . . ? N4 C13 C14 116.4(2) . . ? C15 C14 C16 117.6(2) . . ? C15 C14 C13 118.9(2) . . ? C16 C14 C13 123.5(2) . . ? N2 C15 C14 123.8(2) . . ? C17 C16 C14 119.4(2) . . ? C18 C17 C16 118.5(2) . . ? N2 C18 C17 123.6(2) . . ? O1 C19 O4 121.8(2) . . ? O1 C19 C20 118.7(2) . . ? O4 C19 C20 119.5(2) . . ? C26 C20 C21 119.5(2) . . ? C26 C20 C19 120.3(2) . . ? C21 C20 C19 120.1(2) . . ? C22 C21 C20 120.0(2) . . ? C21 C22 C23 120.0(3) . . ? C22 C23 C24 120.5(2) . . ? C26 C24 C23 119.1(2) . . ? C26 C24 C25 120.5(2) . . ? C23 C24 C25 120.4(2) . . ? O3 C25 O2 121.9(2) . . ? O3 C25 C24 119.5(2) . . ? O2 C25 C24 118.5(2) . . ? O3 C25 Cd1 62.93(12) . 1_455 ? O2 C25 Cd1 59.54(12) . 1_455 ? C24 C25 Cd1 169.45(16) . 1_455 ? C24 C26 C20 120.9(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.608 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 930203' ####################################################################### # # 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_lj-7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 Cd N4 O6' _chemical_formula_weight 600.89 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' Cd Cd -0.8075 1.2024 '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 10.1198(12) _cell_length_b 10.1243(12) _cell_length_c 13.3200(16) _cell_angle_alpha 99.284(2) _cell_angle_beta 99.883(2) _cell_angle_gamma 109.078(2) _cell_volume 1235.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 25.00 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.830 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6328 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4304 _reflns_number_gt 3863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT+ (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (1998)' _refine_special_details ; & nbsp;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^)+(0.0368P)^2^+0.1129P] 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 4304 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Cd1 Cd 0.361499(19) 0.085275(19) 0.939389(15) 0.02236(8) Uani 1 1 d . . . N1 N 0.4538(2) 0.0946(2) 0.78856(18) 0.0284(5) Uani 1 1 d . . . O1 O 0.2394(2) -0.0944(2) 1.01317(17) 0.0374(5) Uani 1 1 d . . . C1 C 0.4188(4) 0.1829(4) 0.7338(3) 0.0463(9) Uani 1 1 d . . . H1A H 0.3538 0.2231 0.7531 0.056 Uiso 1 1 calc R . . O2 O 0.40490(19) -0.15803(19) 0.95348(15) 0.0297(4) Uani 1 1 d . . . N2 N -0.1316(2) 0.0119(2) 0.18372(19) 0.0309(5) Uani 1 1 d . . . C2 C 0.4746(4) 0.2172(4) 0.6499(3) 0.0504(9) Uani 1 1 d . . . H2A H 0.4470 0.2792 0.6140 0.060 Uiso 1 1 calc R . . O3 O 0.2984(2) -0.76660(19) 1.06394(15) 0.0320(5) Uani 1 1 d . . . N3 N 0.5973(2) 0.2801(3) 0.47797(18) 0.0299(5) Uani 1 1 d . . . H3A H 0.5349 0.3117 0.4986 0.036 Uiso 1 1 calc R . . C3 C 0.5718(3) 0.1592(3) 0.6192(2) 0.0291(6) Uani 1 1 d . . . O4 O 0.3519(2) -0.6798(2) 0.92969(16) 0.0358(5) Uani 1 1 d . . . N4 N 0.4036(2) 0.2963(2) 0.29265(17) 0.0258(5) Uani 1 1 d . . . H4B H 0.3788 0.2505 0.2280 0.031 Uiso 1 1 calc R . . C4 C 0.6057(3) 0.0668(3) 0.6746(2) 0.0327(7) Uani 1 1 d . . . H4A H 0.6695 0.0241 0.6561 0.039 Uiso 1 1 calc R . . O5 O 0.7262(3) 0.1396(3) 0.50539(19) 0.0538(6) Uani 1 1 d . . . C5 C 0.5453(3) 0.0370(3) 0.7577(2) 0.0302(6) Uani 1 1 d . . . H5A H 0.5697 -0.0262 0.7938 0.036 Uiso 1 1 calc R . . O6 O 0.3301(2) 0.3249(2) 0.44352(16) 0.0397(5) Uani 1 1 d . . . C6 C 0.6393(3) 0.1923(3) 0.5291(2) 0.0322(7) Uani 1 1 d . . . C7 C 0.6503(3) 0.3260(3) 0.3893(2) 0.0261(6) Uani 1 1 d . . . H7A H 0.6446 0.2411 0.3390 0.031 Uiso 1 1 calc R . . C8 C 0.8069(3) 0.4296(3) 0.4251(2) 0.0343(7) Uani 1 1 d . . . H8A H 0.8149 0.5098 0.4797 0.041 Uiso 1 1 calc R . . H8B H 0.8665 0.3806 0.4545 0.041 Uiso 1 1 calc R . . C9 C 0.8618(3) 0.4863(3) 0.3348(3) 0.0396(8) Uani 1 1 d . . . H9A H 0.9599 0.5548 0.3607 0.048 Uiso 1 1 calc R . . H9B H 0.8620 0.4075 0.2827 0.048 Uiso 1 1 calc R . . C10 C 0.7670(3) 0.5582(3) 0.2850(3) 0.0383(7) Uani 1 1 d . . . H10A H 0.8003 0.5901 0.2258 0.046 Uiso 1 1 calc R . . H10B H 0.7733 0.6420 0.3355 0.046 Uiso 1 1 calc R . . C11 C 0.6115(3) 0.4544(3) 0.2482(2) 0.0316(7) Uani 1 1 d . . . H11A H 0.5521 0.5034 0.2182 0.038 Uiso 1 1 calc R . . H11B H 0.6048 0.3749 0.1936 0.038 Uiso 1 1 calc R . . C12 C 0.5537(3) 0.3962(3) 0.3361(2) 0.0249(6) Uani 1 1 d . . . H12A H 0.5540 0.4766 0.3882 0.030 Uiso 1 1 calc R . . C13 C 0.3038(3) 0.2731(3) 0.3489(2) 0.0267(6) Uani 1 1 d . . . C14 C 0.1527(3) 0.1769(3) 0.2898(2) 0.0254(6) Uani 1 1 d . . . C15 C 0.0386(3) 0.1898(3) 0.3295(2) 0.0398(8) Uani 1 1 d . . . H15A H 0.0556 0.2539 0.3929 0.048 Uiso 1 1 calc R . . C16 C -0.1003(3) 0.1069(3) 0.2743(3) 0.0416(8) Uani 1 1 d . . . H16A H -0.1758 0.1176 0.3016 0.050 Uiso 1 1 calc R . . C17 C -0.0210(3) -0.0043(3) 0.1479(2) 0.0308(6) Uani 1 1 d . . . H17A H -0.0409 -0.0723 0.0859 0.037 Uiso 1 1 calc R . . C18 C 0.1212(3) 0.0749(3) 0.1982(2) 0.0265(6) Uani 1 1 d . . . H18A H 0.1949 0.0595 0.1708 0.032 Uiso 1 1 calc R . . C19 C 0.3006(3) -0.1822(3) 0.9977(2) 0.0261(6) Uani 1 1 d . . . C20 C 0.2502(3) -0.3181(3) 1.0356(2) 0.0239(6) Uani 1 1 d . . . C21 C 0.1542(3) -0.3342(3) 1.0996(2) 0.0345(7) Uani 1 1 d . . . H21A H 0.1182 -0.2623 1.1169 0.041 Uiso 1 1 calc R . . C22 C 0.1118(3) -0.4564(3) 1.1378(3) 0.0405(8) Uani 1 1 d . . . H22A H 0.0493 -0.4654 1.1822 0.049 Uiso 1 1 calc R . . C23 C 0.1619(3) -0.5654(3) 1.1103(2) 0.0339(7) Uani 1 1 d . . . H23A H 0.1323 -0.6478 1.1359 0.041 Uiso 1 1 calc R . . C24 C 0.2563(3) -0.5528(3) 1.0447(2) 0.0235(6) Uani 1 1 d . . . C25 C 0.3002(3) -0.4285(3) 1.0080(2) 0.0233(6) Uani 1 1 d . . . H25A H 0.3637 -0.4188 0.9644 0.028 Uiso 1 1 calc R . . C26 C 0.3065(3) -0.6732(3) 1.0107(2) 0.0240(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.02414(11) 0.02109(11) 0.02261(12) 0.00627(8) 0.00558(8) 0.00871(8) N1 0.0334(13) 0.0295(13) 0.0256(13) 0.0104(10) 0.0077(10) 0.0134(10) O1 0.0501(13) 0.0261(11) 0.0461(13) 0.0137(9) 0.0165(10) 0.0218(10) C1 0.069(2) 0.057(2) 0.045(2) 0.0282(17) 0.0307(18) 0.0469(19) O2 0.0276(10) 0.0256(10) 0.0312(11) 0.0109(8) 0.0054(9) 0.0027(8) N2 0.0236(12) 0.0323(13) 0.0340(14) 0.0032(11) 0.0045(10) 0.0098(10) C2 0.084(3) 0.059(2) 0.049(2) 0.0370(18) 0.041(2) 0.055(2) O3 0.0478(12) 0.0233(10) 0.0303(11) 0.0105(9) 0.0117(9) 0.0170(9) N3 0.0304(12) 0.0432(14) 0.0255(13) 0.0131(11) 0.0140(10) 0.0196(11) C3 0.0356(16) 0.0322(16) 0.0223(14) 0.0081(12) 0.0080(12) 0.0145(13) O4 0.0515(13) 0.0332(11) 0.0350(12) 0.0120(9) 0.0219(10) 0.0237(10) N4 0.0239(11) 0.0311(12) 0.0186(12) 0.0008(10) 0.0032(9) 0.0086(10) C4 0.0374(16) 0.0385(17) 0.0296(16) 0.0089(13) 0.0093(13) 0.0224(14) O5 0.0719(16) 0.0708(17) 0.0543(16) 0.0336(13) 0.0383(13) 0.0513(14) C5 0.0366(16) 0.0301(15) 0.0268(15) 0.0089(12) 0.0039(13) 0.0167(13) O6 0.0280(11) 0.0609(14) 0.0245(11) -0.0023(10) 0.0051(9) 0.0154(10) C6 0.0358(16) 0.0357(16) 0.0305(16) 0.0103(13) 0.0129(13) 0.0162(13) C7 0.0271(14) 0.0315(15) 0.0220(14) 0.0076(12) 0.0085(11) 0.0117(12) C8 0.0251(14) 0.0475(18) 0.0292(16) 0.0112(14) 0.0039(12) 0.0121(13) C9 0.0276(15) 0.0470(19) 0.0431(19) 0.0142(15) 0.0119(14) 0.0086(14) C10 0.0345(16) 0.0384(17) 0.0378(18) 0.0151(14) 0.0091(14) 0.0048(14) C11 0.0305(15) 0.0340(16) 0.0291(16) 0.0117(13) 0.0062(12) 0.0087(13) C12 0.0218(13) 0.0266(14) 0.0233(14) 0.0015(11) 0.0046(11) 0.0075(11) C13 0.0253(14) 0.0328(15) 0.0247(15) 0.0039(12) 0.0051(12) 0.0159(12) C14 0.0236(14) 0.0284(15) 0.0253(15) 0.0069(12) 0.0041(11) 0.0115(11) C15 0.0289(16) 0.0477(19) 0.0337(17) -0.0103(14) 0.0054(13) 0.0126(14) C16 0.0297(16) 0.0473(19) 0.043(2) -0.0059(15) 0.0083(14) 0.0162(14) C17 0.0304(15) 0.0290(15) 0.0266(15) 0.0009(12) 0.0035(12) 0.0071(12) C18 0.0237(14) 0.0296(15) 0.0271(15) 0.0072(12) 0.0078(12) 0.0097(12) C19 0.0295(14) 0.0188(13) 0.0221(14) 0.0031(11) -0.0028(12) 0.0040(11) C20 0.0249(14) 0.0199(13) 0.0255(14) 0.0058(11) 0.0030(11) 0.0075(11) C21 0.0377(16) 0.0267(15) 0.0469(19) 0.0083(13) 0.0189(14) 0.0175(13) C22 0.0479(19) 0.0408(18) 0.050(2) 0.0206(16) 0.0355(16) 0.0225(15) C23 0.0426(17) 0.0266(15) 0.0408(18) 0.0191(13) 0.0197(14) 0.0134(13) C24 0.0264(14) 0.0199(13) 0.0241(14) 0.0043(11) 0.0058(11) 0.0090(11) C25 0.0209(13) 0.0246(14) 0.0242(14) 0.0080(11) 0.0071(11) 0.0059(11) C26 0.0200(13) 0.0201(13) 0.0266(15) 0.0023(11) 0.0022(11) 0.0034(11) _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 Cd1 O1 2.308(2) . ? Cd1 O2 2.3519(18) 2_657 ? Cd1 N1 2.359(2) . ? Cd1 O3 2.3655(19) 1_565 ? Cd1 N2 2.396(2) 2_556 ? Cd1 O4 2.4351(19) 1_565 ? Cd1 C26 2.741(3) 1_565 ? N1 C5 1.332(4) . ? N1 C1 1.336(4) . ? O1 C19 1.249(3) . ? C1 C2 1.379(4) . ? O2 C19 1.270(3) . ? O2 Cd1 2.3520(18) 2_657 ? N2 C16 1.333(4) . ? N2 C17 1.336(4) . ? N2 Cd1 2.396(2) 2_556 ? C2 C3 1.385(4) . ? O3 C26 1.261(3) . ? O3 Cd1 2.3656(19) 1_545 ? N3 C6 1.333(4) . ? N3 C7 1.459(3) . ? C3 C4 1.372(4) . ? C3 C6 1.510(4) . ? O4 C26 1.244(3) . ? O4 Cd1 2.4351(19) 1_545 ? N4 C13 1.341(3) . ? N4 C12 1.473(3) . ? C4 C5 1.382(4) . ? O5 C6 1.226(3) . ? O6 C13 1.231(3) . ? C7 C8 1.527(4) . ? C7 C12 1.531(4) . ? C8 C9 1.526(4) . ? C9 C10 1.511(4) . ? C10 C11 1.520(4) . ? C11 C12 1.514(4) . ? C13 C14 1.507(4) . ? C14 C18 1.379(4) . ? C14 C15 1.384(4) . ? C15 C16 1.377(4) . ? C17 C18 1.380(4) . ? C19 C20 1.504(4) . ? C20 C21 1.386(4) . ? C20 C25 1.394(4) . ? C21 C22 1.380(4) . ? C22 C23 1.381(4) . ? C23 C24 1.392(4) . ? C24 C25 1.388(4) . ? C24 C26 1.501(4) . ? C26 Cd1 2.741(3) 1_545 ? 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 Cd1 O2 100.08(7) . 2_657 ? O1 Cd1 N1 135.69(8) . . ? O2 Cd1 N1 90.87(7) 2_657 . ? O1 Cd1 O3 83.41(7) . 1_565 ? O2 Cd1 O3 91.05(7) 2_657 1_565 ? N1 Cd1 O3 139.62(7) . 1_565 ? O1 Cd1 N2 79.67(8) . 2_556 ? O2 Cd1 N2 172.44(7) 2_657 2_556 ? N1 Cd1 N2 84.23(8) . 2_556 ? O3 Cd1 N2 96.41(7) 1_565 2_556 ? O1 Cd1 O4 133.34(7) . 1_565 ? O2 Cd1 O4 99.36(7) 2_657 1_565 ? N1 Cd1 O4 85.69(7) . 1_565 ? O3 Cd1 O4 54.24(6) 1_565 1_565 ? N2 Cd1 O4 86.04(8) 2_556 1_565 ? O1 Cd1 C26 108.28(8) . 1_565 ? O2 Cd1 C26 97.48(7) 2_657 1_565 ? N1 Cd1 C26 112.66(8) . 1_565 ? O3 Cd1 C26 27.34(7) 1_565 1_565 ? N2 Cd1 C26 89.73(8) 2_556 1_565 ? O4 Cd1 C26 26.98(7) 1_565 1_565 ? C5 N1 C1 116.9(3) . . ? C5 N1 Cd1 129.25(18) . . ? C1 N1 Cd1 113.47(19) . . ? C19 O1 Cd1 101.84(17) . . ? N1 C1 C2 123.1(3) . . ? C19 O2 Cd1 117.65(17) . 2_657 ? C16 N2 C17 117.2(2) . . ? C16 N2 Cd1 124.60(19) . 2_556 ? C17 N2 Cd1 116.31(19) . 2_556 ? C1 C2 C3 119.8(3) . . ? C26 O3 Cd1 93.16(16) . 1_545 ? C6 N3 C7 124.2(2) . . ? C4 C3 C2 116.9(3) . . ? C4 C3 C6 119.8(3) . . ? C2 C3 C6 123.3(3) . . ? C26 O4 Cd1 90.36(16) . 1_545 ? C13 N4 C12 123.2(2) . . ? C3 C4 C5 120.1(3) . . ? N1 C5 C4 123.2(3) . . ? O5 C6 N3 123.2(3) . . ? O5 C6 C3 121.1(3) . . ? N3 C6 C3 115.7(2) . . ? N3 C7 C8 110.8(2) . . ? N3 C7 C12 108.9(2) . . ? C8 C7 C12 111.0(2) . . ? C9 C8 C7 111.8(2) . . ? C10 C9 C8 110.2(2) . . ? C9 C10 C11 110.4(2) . . ? C12 C11 C10 112.5(2) . . ? N4 C12 C11 108.4(2) . . ? N4 C12 C7 112.8(2) . . ? C11 C12 C7 110.4(2) . . ? O6 C13 N4 123.6(2) . . ? O6 C13 C14 120.2(2) . . ? N4 C13 C14 116.2(2) . . ? C18 C14 C15 117.7(2) . . ? C18 C14 C13 123.6(2) . . ? C15 C14 C13 118.7(2) . . ? C16 C15 C14 119.4(3) . . ? N2 C16 C15 123.1(3) . . ? N2 C17 C18 123.3(3) . . ? C14 C18 C17 119.1(3) . . ? O1 C19 O2 121.9(2) . . ? O1 C19 C20 118.2(3) . . ? O2 C19 C20 119.9(2) . . ? C21 C20 C25 119.2(2) . . ? C21 C20 C19 120.2(2) . . ? C25 C20 C19 120.6(2) . . ? C22 C21 C20 120.4(3) . . ? C21 C22 C23 120.1(3) . . ? C22 C23 C24 120.5(3) . . ? C25 C24 C23 118.9(2) . . ? C25 C24 C26 120.1(2) . . ? C23 C24 C26 120.9(2) . . ? C24 C25 C20 120.8(2) . . ? O4 C26 O3 121.8(2) . . ? O4 C26 C24 119.2(2) . . ? O3 C26 C24 119.0(2) . . ? O4 C26 Cd1 62.66(14) . 1_545 ? O3 C26 Cd1 59.50(14) . 1_545 ? C24 C26 Cd1 172.64(17) . 1_545 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.341 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 931341'