# 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_compound1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H39 Co N6 O8' _chemical_formula_sum 'C35 H39 Co N6 O8' _chemical_formula_weight 730.65 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 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' 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 43.577(3) _cell_length_b 7.6541(5) _cell_length_c 21.0472(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.2070(10) _cell_angle_gamma 90.00 _cell_volume 7001.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 26.820 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3056 _exptl_absorpt_coefficient_mu 0.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20307 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 54 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 0.94 _diffrn_reflns_theta_max 26.82 _reflns_number_total 7429 _reflns_number_gt 5774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+2.0376P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7510 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.004 _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 0.668476(6) 0.29681(3) 0.178291(13) 0.02083(9) Uani 1 1 d . . . N1 N 0.71757(4) 0.2434(2) 0.18065(8) 0.0227(4) Uani 1 1 d . . . O1 O 0.72198(4) -0.2427(2) 0.10312(9) 0.0449(5) Uani 1 1 d . . . C1 C 0.73903(5) 0.3528(3) 0.20609(10) 0.0276(5) Uani 1 1 d . . . H1A H 0.7328 0.4566 0.2241 0.033 Uiso 1 1 calc R . . O1W O 0.67662(4) 0.5683(2) 0.16358(9) 0.0340(4) Uani 1 1 d . . . H1WA H 0.6715(7) 0.642(5) 0.1895(16) 0.070(11) Uiso 1 1 d . . . H1WB H 0.6904(7) 0.612(4) 0.1458(14) 0.052(9) Uiso 1 1 d . . . N2 N 0.76777(4) -0.1061(2) 0.12449(8) 0.0240(4) Uani 1 1 d . . . H2B H 0.7873 -0.1169 0.1219 0.029 Uiso 1 1 calc R . . C2 C 0.77020(5) 0.3175(3) 0.20667(10) 0.0286(5) Uani 1 1 d . . . H2A H 0.7845 0.3954 0.2255 0.034 Uiso 1 1 calc R . . O2 O 0.50389(5) 0.1555(3) 0.12681(17) 0.1040(11) Uani 1 1 d . . . O3 O 0.40176(4) -0.8678(3) -0.05077(10) 0.0549(5) Uani 1 1 d . . . N3 N 0.61883(4) 0.3498(2) 0.16475(8) 0.0271(4) Uani 1 1 d . . . C3 C 0.77979(5) 0.1653(3) 0.17901(10) 0.0252(5) Uani 1 1 d . . . H3A H 0.8006 0.1404 0.1781 0.030 Uiso 1 1 calc R . . O4 O 0.66366(3) 0.03491(19) 0.20123(7) 0.0298(3) Uani 1 1 d . . . C4 C 0.75777(4) 0.0495(2) 0.15247(9) 0.0206(4) Uani 1 1 d . . . N4 N 0.55274(4) 0.0875(3) 0.10795(11) 0.0421(5) Uani 1 1 d . . . H4A H 0.5638 0.0091 0.0912 0.051 Uiso 1 1 calc R . . O5 O 0.65434(4) -0.2110(2) 0.25227(8) 0.0378(4) Uani 1 1 d . . . N5 N 0.36393(4) -0.8490(3) 0.01757(9) 0.0341(5) Uani 1 1 d . . . H5B H 0.3553 -0.7853 0.0448 0.041 Uiso 1 1 calc R . . C5 C 0.72680(5) 0.0936(3) 0.15474(9) 0.0227(4) Uani 1 1 d . . . H5A H 0.7120 0.0162 0.1376 0.027 Uiso 1 1 calc R . . O6 O 0.66512(4) 0.3179(2) 0.37701(7) 0.0318(4) Uani 1 1 d . . . C6 C 0.75002(5) -0.2406(3) 0.10129(10) 0.0258(5) Uani 1 1 d . . . N6 N 0.33508(4) -1.2291(2) -0.07597(8) 0.0250(4) Uani 1 1 d . . . O7 O 0.67183(3) 0.3491(2) 0.27453(7) 0.0308(4) Uani 1 1 d . . . C7 C 0.76702(5) -0.3878(3) 0.07109(11) 0.0284(5) Uani 1 1 d . . . H7A H 0.7813 -0.4406 0.1030 0.034 Uiso 1 1 calc R . . H7B H 0.7788 -0.3406 0.0377 0.034 Uiso 1 1 calc R . . C8 C 0.74516(5) -0.5271(3) 0.04298(10) 0.0255(5) Uani 1 1 d . . . H8A H 0.7312 -0.4738 0.0106 0.031 Uiso 1 1 calc R . . H8B H 0.7330 -0.5710 0.0763 0.031 Uiso 1 1 calc R . . C9 C 0.76122(5) -0.6804(3) 0.01342(10) 0.0257(5) Uani 1 1 d . . . H9A H 0.7754 -0.7331 0.0455 0.031 Uiso 1 1 calc R . . H9B H 0.7731 -0.6374 -0.0205 0.031 Uiso 1 1 calc R . . C10 C 0.60031(5) 0.2214(3) 0.14161(10) 0.0287(5) Uani 1 1 d . . . H10A H 0.6093 0.1160 0.1312 0.034 Uiso 1 1 calc R . . C11 C 0.60548(5) 0.5008(3) 0.17972(13) 0.0393(6) Uani 1 1 d . . . H11A H 0.6178 0.5914 0.1964 0.047 Uiso 1 1 calc R . . C12 C 0.57423(6) 0.5260(4) 0.17131(15) 0.0551(8) Uani 1 1 d . . . H12A H 0.5658 0.6327 0.1821 0.066 Uiso 1 1 calc R . . C13 C 0.55527(6) 0.3936(4) 0.14695(15) 0.0501(7) Uani 1 1 d . . . H13A H 0.5341 0.4100 0.1406 0.060 Uiso 1 1 calc R . . C14 C 0.56858(5) 0.2363(3) 0.13222(12) 0.0332(5) Uani 1 1 d . . . C15 C 0.52233(6) 0.0530(4) 0.10777(16) 0.0545(8) Uani 1 1 d . . . C16 C 0.51373(6) -0.1267(4) 0.08161(19) 0.0654(10) Uani 1 1 d . . . H16A H 0.5214 -0.1381 0.0397 0.078 Uiso 1 1 calc R . . H16B H 0.5240 -0.2141 0.1089 0.078 Uiso 1 1 calc R . . C17 C 0.47989(6) -0.1645(4) 0.07644(16) 0.0561(8) Uani 1 1 d . . . H17A H 0.4695 -0.0788 0.0485 0.067 Uiso 1 1 calc R . . H17B H 0.4720 -0.1528 0.1182 0.067 Uiso 1 1 calc R . . C18 C 0.47249(6) -0.3465(4) 0.05075(16) 0.0551(8) Uani 1 1 d . . . H18A H 0.4812 -0.3592 0.0098 0.066 Uiso 1 1 calc R . . H18B H 0.4824 -0.4318 0.0796 0.066 Uiso 1 1 calc R . . C19 C 0.43846(6) -0.3863(4) 0.04258(14) 0.0472(7) Uani 1 1 d . . . H19A H 0.4286 -0.3033 0.0128 0.057 Uiso 1 1 calc R . . H19B H 0.4296 -0.3708 0.0832 0.057 Uiso 1 1 calc R . . C20 C 0.43150(5) -0.5706(3) 0.01851(13) 0.0403(6) Uani 1 1 d . . . H20A H 0.4396 -0.6545 0.0500 0.048 Uiso 1 1 calc R . . H20B H 0.4416 -0.5902 -0.0204 0.048 Uiso 1 1 calc R . . C21 C 0.39698(5) -0.5988(3) 0.00567(12) 0.0371(6) Uani 1 1 d . . . H21A H 0.3868 -0.5655 0.0433 0.045 Uiso 1 1 calc R . . H21B H 0.3895 -0.5223 -0.0288 0.045 Uiso 1 1 calc R . . C22 C 0.38819(5) -0.7835(3) -0.01159(12) 0.0358(5) Uani 1 1 d . . . C23 C 0.35240(5) -1.0202(3) 0.00429(10) 0.0296(5) Uani 1 1 d . . . C24 C 0.34912(5) -1.1415(3) 0.05192(11) 0.0358(5) Uani 1 1 d . . . H24A H 0.3538 -1.1127 0.0945 0.043 Uiso 1 1 calc R . . C25 C 0.33863(5) -1.3071(3) 0.03477(11) 0.0350(5) Uani 1 1 d . . . H25A H 0.3357 -1.3906 0.0658 0.042 Uiso 1 1 calc R . . C26 C 0.33266(5) -1.3468(3) -0.02905(11) 0.0306(5) Uani 1 1 d . . . H26A H 0.3267 -1.4601 -0.0401 0.037 Uiso 1 1 calc R . . C27 C 0.34405(5) -1.0672(3) -0.05844(10) 0.0271(5) Uani 1 1 d . . . H27A H 0.3447 -0.9821 -0.0899 0.033 Uiso 1 1 calc R . . C28 C 0.60031(5) 0.2723(4) 0.32769(12) 0.0425(6) Uani 1 1 d . . . H28A H 0.6018 0.3795 0.3484 0.051 Uiso 1 1 calc R . . C29 C 0.57204(6) 0.1902(4) 0.31982(14) 0.0580(8) Uani 1 1 d . . . H29A H 0.5546 0.2444 0.3333 0.070 Uiso 1 1 calc R . . C30 C 0.56996(6) 0.0273(5) 0.29181(14) 0.0591(9) Uani 1 1 d . . . H30A H 0.5511 -0.0303 0.2874 0.071 Uiso 1 1 calc R . . C31 C 0.59567(5) -0.0496(4) 0.27050(12) 0.0424(6) Uani 1 1 d . . . H31A H 0.5941 -0.1610 0.2529 0.051 Uiso 1 1 calc R . . C32 C 0.62424(5) 0.0352(3) 0.27456(10) 0.0266(5) Uani 1 1 d . . . C33 C 0.62662(5) 0.1977(3) 0.30523(10) 0.0254(5) Uani 1 1 d . . . C34 C 0.65675(5) 0.2941(3) 0.31919(10) 0.0239(4) Uani 1 1 d . . . C35 C 0.64970(5) -0.0531(3) 0.24138(10) 0.0245(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 0.02079(15) 0.02053(15) 0.02138(15) -0.00226(11) 0.00299(11) -0.00129(11) N1 0.0258(9) 0.0234(9) 0.0191(9) -0.0014(7) 0.0030(7) 0.0010(7) O1 0.0269(9) 0.0340(9) 0.0761(13) -0.0206(9) 0.0196(9) -0.0059(7) C1 0.0335(12) 0.0245(11) 0.0243(11) -0.0074(9) 0.0001(9) 0.0028(9) O1W 0.0379(10) 0.0239(9) 0.0419(10) -0.0022(8) 0.0142(8) -0.0048(7) N2 0.0202(8) 0.0216(9) 0.0304(10) -0.0069(7) 0.0025(7) 0.0014(7) C2 0.0274(11) 0.0286(12) 0.0287(11) -0.0069(9) -0.0039(9) -0.0047(9) O2 0.0326(11) 0.0794(17) 0.203(3) -0.075(2) 0.0287(15) -0.0153(11) O3 0.0445(11) 0.0555(12) 0.0680(13) -0.0328(10) 0.0269(10) -0.0149(9) N3 0.0247(9) 0.0286(10) 0.0278(10) -0.0018(8) 0.0017(8) -0.0019(8) C3 0.0223(10) 0.0264(11) 0.0268(11) 0.0000(9) 0.0007(9) 0.0018(9) O4 0.0333(8) 0.0235(8) 0.0341(9) -0.0006(7) 0.0131(7) -0.0002(7) C4 0.0260(10) 0.0191(10) 0.0168(10) -0.0011(8) 0.0014(8) -0.0002(8) N4 0.0237(10) 0.0398(12) 0.0628(14) -0.0202(11) 0.0023(9) -0.0043(9) O5 0.0415(9) 0.0218(8) 0.0506(10) 0.0023(7) 0.0079(8) -0.0007(7) N5 0.0331(10) 0.0378(11) 0.0320(10) -0.0145(9) 0.0072(8) -0.0068(9) C5 0.0246(10) 0.0214(10) 0.0222(10) -0.0015(8) 0.0026(8) -0.0019(8) O6 0.0340(8) 0.0398(9) 0.0214(8) -0.0022(7) 0.0010(6) -0.0071(7) C6 0.0300(12) 0.0201(10) 0.0278(11) -0.0021(8) 0.0053(9) -0.0022(9) N6 0.0197(8) 0.0285(10) 0.0269(9) -0.0017(8) 0.0018(7) -0.0004(7) O7 0.0330(8) 0.0369(9) 0.0230(8) -0.0054(7) 0.0063(7) -0.0111(7) C7 0.0282(11) 0.0212(11) 0.0367(12) -0.0047(9) 0.0077(9) -0.0009(9) C8 0.0301(11) 0.0205(10) 0.0263(11) -0.0036(9) 0.0047(9) -0.0014(9) C9 0.0317(12) 0.0202(10) 0.0259(11) -0.0032(8) 0.0062(9) -0.0021(9) C10 0.0242(11) 0.0289(12) 0.0329(12) -0.0057(10) 0.0017(9) 0.0000(9) C11 0.0284(12) 0.0321(13) 0.0565(16) -0.0124(12) -0.0039(11) -0.0013(10) C12 0.0347(14) 0.0367(15) 0.092(2) -0.0217(15) -0.0082(14) 0.0080(12) C13 0.0238(12) 0.0435(15) 0.081(2) -0.0175(15) -0.0094(13) 0.0049(11) C14 0.0259(11) 0.0345(13) 0.0388(13) -0.0078(10) -0.0014(10) -0.0036(10) C15 0.0282(13) 0.0480(17) 0.088(2) -0.0233(16) 0.0079(14) -0.0065(12) C16 0.0337(15) 0.0465(17) 0.115(3) -0.0269(18) 0.0013(16) -0.0099(13) C17 0.0344(14) 0.0579(19) 0.077(2) -0.0240(16) 0.0109(14) -0.0164(13) C18 0.0355(14) 0.0476(17) 0.083(2) -0.0175(15) 0.0070(14) -0.0126(13) C19 0.0381(14) 0.0454(16) 0.0592(18) -0.0159(13) 0.0099(13) -0.0132(12) C20 0.0348(13) 0.0392(14) 0.0472(15) -0.0089(12) 0.0045(11) -0.0078(11) C21 0.0335(12) 0.0379(14) 0.0406(14) -0.0094(11) 0.0066(11) -0.0058(11) C22 0.0299(12) 0.0410(14) 0.0367(13) -0.0120(11) 0.0045(10) -0.0051(11) C23 0.0235(11) 0.0345(12) 0.0312(12) -0.0090(10) 0.0055(9) -0.0018(9) C24 0.0375(13) 0.0476(14) 0.0224(11) -0.0062(10) 0.0019(10) 0.0012(11) C25 0.0363(13) 0.0392(13) 0.0301(12) 0.0058(10) 0.0064(10) 0.0056(11) C26 0.0237(11) 0.0313(12) 0.0371(13) -0.0028(10) 0.0045(10) -0.0005(9) C27 0.0261(11) 0.0303(12) 0.0251(11) -0.0024(9) 0.0029(9) -0.0032(9) C28 0.0324(13) 0.0550(16) 0.0406(14) -0.0161(12) 0.0073(11) 0.0056(12) C29 0.0290(14) 0.092(3) 0.0543(18) -0.0212(17) 0.0129(13) 0.0020(15) C30 0.0293(14) 0.090(2) 0.0593(19) -0.0142(17) 0.0135(13) -0.0217(15) C31 0.0340(13) 0.0484(16) 0.0458(15) -0.0075(12) 0.0102(11) -0.0166(12) C32 0.0262(11) 0.0290(11) 0.0252(11) 0.0023(9) 0.0048(9) -0.0043(9) C33 0.0253(11) 0.0312(12) 0.0200(10) 0.0006(9) 0.0034(8) 0.0007(9) C34 0.0274(11) 0.0188(10) 0.0255(11) -0.0041(9) 0.0021(9) 0.0040(9) C35 0.0245(10) 0.0229(11) 0.0256(11) -0.0023(9) -0.0011(9) -0.0049(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 Co1 O7 2.0593(14) . ? Co1 O4 2.0762(15) . ? Co1 O1W 2.1345(17) . ? Co1 N1 2.1752(17) . ? Co1 N3 2.1988(17) . ? Co1 N6 2.2092(18) 5_645 ? N1 C1 1.338(3) . ? N1 C5 1.344(3) . ? O1 C6 1.225(3) . ? C1 C2 1.384(3) . ? N2 C6 1.357(3) . ? N2 C4 1.412(2) . ? C2 C3 1.381(3) . ? O2 C15 1.212(3) . ? O3 C22 1.232(3) . ? N3 C10 1.340(3) . ? N3 C11 1.342(3) . ? C3 C4 1.392(3) . ? O4 C35 1.270(2) . ? C4 C5 1.395(3) . ? N4 C15 1.351(3) . ? N4 C14 1.408(3) . ? O5 C35 1.244(2) . ? N5 C22 1.357(3) . ? N5 C23 1.424(3) . ? O6 C34 1.258(2) . ? C6 C7 1.513(3) . ? N6 C27 1.343(3) . ? N6 C26 1.346(3) . ? N6 Co1 2.2093(18) 5_645 ? O7 C34 1.258(2) . ? C7 C8 1.521(3) . ? C8 C9 1.522(3) . ? C9 C9 1.527(4) 7_635 ? C10 C14 1.387(3) . ? C11 C12 1.374(3) . ? C12 C13 1.382(3) . ? C13 C14 1.381(3) . ? C15 C16 1.518(4) . ? C16 C17 1.499(4) . ? C17 C18 1.520(4) . ? C18 C19 1.511(3) . ? C19 C20 1.522(3) . ? C20 C21 1.524(3) . ? C21 C22 1.502(3) . ? C23 C24 1.381(3) . ? C23 C27 1.391(3) . ? C24 C25 1.386(3) . ? C25 C26 1.383(3) . ? C28 C29 1.382(4) . ? C28 C33 1.394(3) . ? C29 C30 1.379(4) . ? C30 C31 1.370(4) . ? C31 C32 1.401(3) . ? C32 C33 1.402(3) . ? C32 C35 1.513(3) . ? C33 C34 1.516(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 O7 Co1 O4 87.70(6) . . ? O7 Co1 O1W 87.30(7) . . ? O4 Co1 O1W 173.94(7) . . ? O7 Co1 N1 90.88(6) . . ? O4 Co1 N1 85.93(6) . . ? O1W Co1 N1 90.72(7) . . ? O7 Co1 N3 95.16(6) . . ? O4 Co1 N3 95.34(6) . . ? O1W Co1 N3 88.53(7) . . ? N1 Co1 N3 173.88(6) . . ? O7 Co1 N6 177.64(6) . 5_645 ? O4 Co1 N6 89.96(6) . 5_645 ? O1W Co1 N6 95.01(7) . 5_645 ? N1 Co1 N6 88.67(6) . 5_645 ? N3 Co1 N6 85.34(6) . 5_645 ? C1 N1 C5 118.39(18) . . ? C1 N1 Co1 123.29(14) . . ? C5 N1 Co1 118.32(14) . . ? N1 C1 C2 122.54(19) . . ? C6 N2 C4 127.23(17) . . ? C3 C2 C1 119.2(2) . . ? C10 N3 C11 117.16(19) . . ? C10 N3 Co1 118.20(14) . . ? C11 N3 Co1 124.61(15) . . ? C2 C3 C4 119.00(19) . . ? C35 O4 Co1 136.74(13) . . ? C3 C4 C5 118.19(18) . . ? C3 C4 N2 118.65(18) . . ? C5 C4 N2 123.16(18) . . ? C15 N4 C14 127.8(2) . . ? C22 N5 C23 121.78(19) . . ? N1 C5 C4 122.62(19) . . ? O1 C6 N2 122.83(19) . . ? O1 C6 C7 121.56(19) . . ? N2 C6 C7 115.59(18) . . ? C27 N6 C26 116.91(19) . . ? C27 N6 Co1 118.83(14) . 5_645 ? C26 N6 Co1 123.68(15) . 5_645 ? C34 O7 Co1 131.81(14) . . ? C6 C7 C8 111.94(17) . . ? C7 C8 C9 113.95(17) . . ? C8 C9 C9 112.8(2) . 7_635 ? N3 C10 C14 124.0(2) . . ? N3 C11 C12 122.3(2) . . ? C11 C12 C13 120.3(2) . . ? C14 C13 C12 118.2(2) . . ? C13 C14 C10 118.1(2) . . ? C13 C14 N4 125.7(2) . . ? C10 C14 N4 116.2(2) . . ? O2 C15 N4 123.1(2) . . ? O2 C15 C16 123.7(2) . . ? N4 C15 C16 113.2(2) . . ? C17 C16 C15 114.6(2) . . ? C16 C17 C18 112.6(2) . . ? C19 C18 C17 114.0(2) . . ? C18 C19 C20 113.3(2) . . ? C19 C20 C21 111.1(2) . . ? C22 C21 C20 114.0(2) . . ? O3 C22 N5 122.5(2) . . ? O3 C22 C21 121.9(2) . . ? N5 C22 C21 115.6(2) . . ? C24 C23 C27 118.8(2) . . ? C24 C23 N5 122.0(2) . . ? C27 C23 N5 119.2(2) . . ? C23 C24 C25 118.4(2) . . ? C26 C25 C24 119.3(2) . . ? N6 C26 C25 123.1(2) . . ? N6 C27 C23 123.4(2) . . ? C29 C28 C33 121.4(2) . . ? C30 C29 C28 119.5(2) . . ? C31 C30 C29 119.9(2) . . ? C30 C31 C32 121.7(2) . . ? C31 C32 C33 118.3(2) . . ? C31 C32 C35 116.3(2) . . ? C33 C32 C35 125.26(18) . . ? C28 C33 C32 119.0(2) . . ? C28 C33 C34 117.22(19) . . ? C32 C33 C34 123.69(18) . . ? O6 C34 O7 122.97(19) . . ? O6 C34 C33 116.33(18) . . ? O7 C34 C33 120.69(18) . . ? O5 C35 O4 123.9(2) . . ? O5 C35 C32 117.64(19) . . ? O4 C35 C32 118.27(18) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.82 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.454 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.147 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.084 0.250 92 15 ' ' 2 0.000 -0.084 0.750 92 15 ' ' 3 0.500 0.416 0.750 92 15 ' ' 4 0.500 0.584 0.250 92 15 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 901806' ####################################################################### # # 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_compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 Co N4 O9' _chemical_formula_sum 'C26 H32 Co N4 O9' _chemical_formula_weight 603.49 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1724(10) _cell_length_b 11.1926(14) _cell_length_c 15.0362(19) _cell_angle_alpha 76.094(2) _cell_angle_beta 89.461(2) _cell_angle_gamma 89.015(2) _cell_volume 1334.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8381 _exptl_absorpt_correction_T_max 0.8957 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6820 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4710 _reflns_number_gt 3110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+15.0000P] 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 4675 _refine_ls_number_parameters 356 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1235 _refine_ls_R_factor_gt 0.0875 _refine_ls_wR_factor_ref 0.1866 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.993 _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 N1 N 0.0633(6) 0.8264(5) 1.1003(4) 0.0336(13) Uani 1 1 d . A . C1 C -0.0335(8) 0.7816(7) 1.1720(5) 0.0389(17) Uani 1 1 d . . . H1A H -0.1301 0.8239 1.1783 0.047 Uiso 1 1 calc R . . Co1 Co 0.0000 1.0000 1.0000 0.0278(3) Uani 1 2 d S . . O1 O 0.4730(10) 0.6799(8) 1.0067(6) 0.061(2) Uiso 0.704(5) 1 d P A 1 O1' O 0.544(2) 0.7480(18) 1.0510(13) 0.061(2) Uiso 0.296(5) 1 d P A 2 H1WA H 0.2980 1.0682 0.9486 0.073 Uiso 1 1 d R . . H1WB H 0.2795 0.9852 1.0315 0.073 Uiso 1 1 d R . . N2 N 0.3971(7) 0.5920(5) 1.1475(4) 0.0373(14) Uani 1 1 d . A . H2B H 0.4098 0.5234 1.1874 0.045 Uiso 1 1 calc R . . O2W O 0.2886(6) 0.4221(5) 0.4561(4) 0.0528(14) Uani 1 1 d . . . H2WA H 0.2033 0.3792 0.4708 0.063 Uiso 1 1 d R . . H2WB H 0.3202 0.4138 0.4038 0.063 Uiso 1 1 d R . . C2 C 0.0034(9) 0.6756(8) 1.2369(5) 0.047(2) Uani 1 1 d . . . H2A H -0.0675 0.6469 1.2858 0.056 Uiso 1 1 calc R . . Co2 Co 0.5000 0.5000 0.5000 0.0236(3) Uani 1 2 d S . . C3 C 0.1473(8) 0.6123(7) 1.2287(5) 0.0383(17) Uani 1 1 d . . . H3A H 0.1750 0.5403 1.2717 0.046 Uiso 1 1 calc R . . O3 O 1.0499(5) 0.2529(4) 0.5521(3) 0.0513(15) Uani 1 1 d . . . O3W O 0.6126(5) 0.8551(4) 0.8709(3) 0.096(2) Uani 1 1 d . . . H3WA H 0.6764 0.8004 0.8585 0.115 Uiso 1 1 d . . . H3WB H 0.5503 0.8199 0.9146 0.115 Uiso 1 1 d . . . C4 C 0.2491(8) 0.6586(6) 1.1547(5) 0.0332(16) Uani 1 1 d . A . N5 N 0.5649(6) 0.3328(5) 0.6006(4) 0.0293(12) Uani 1 1 d . . . C5 C 0.2026(8) 0.7651(6) 1.0914(5) 0.0327(15) Uani 1 1 d . . . H5A H 0.2701 0.7951 1.0412 0.039 Uiso 1 1 calc R A . O5 O 0.3560(7) 0.5607(5) 0.5953(4) 0.0509(14) Uani 1 1 d . . . O6 O 0.5265(6) 0.6265(5) 0.6855(4) 0.0546(15) Uani 1 1 d . . . N6 N 0.8990(7) 0.1011(5) 0.6410(4) 0.0422(16) Uani 1 1 d . . . H6A H 0.9031 0.0248 0.6698 0.051 Uiso 1 1 calc R . . C6 C 0.5168(11) 0.6223(9) 1.0873(6) 0.062(2) Uani 1 1 d U . . C7 C 0.6640(9) 0.5373(8) 1.0987(6) 0.054(2) Uani 1 1 d . A . H7A H 0.6278 0.4548 1.1000 0.065 Uiso 1 1 calc R . . H7B H 0.7142 0.5350 1.1573 0.065 Uiso 1 1 calc R . . O7 O 0.2992(7) 0.9312(5) 0.8596(4) 0.0572(15) Uani 1 1 d . . . O8 O 0.0359(6) 0.9152(5) 0.8928(4) 0.0547(15) Uani 1 1 d . A . C8 C 0.7915(8) 0.5737(6) 1.0241(5) 0.0385(17) Uani 1 1 d . . . H8A H 0.8324 0.6544 1.0244 0.046 Uiso 1 1 calc R A . H8B H 0.7413 0.5790 0.9650 0.046 Uiso 1 1 calc R . . C9 C 0.9340(8) 0.4819(6) 1.0366(5) 0.0366(17) Uani 1 1 d . . . H9A H 0.8929 0.4016 1.0351 0.044 Uiso 1 1 calc R . . H9B H 0.9821 0.4752 1.0964 0.044 Uiso 1 1 calc R . . C18 C 0.1394(9) 0.8092(6) 0.7890(5) 0.0344(16) Uani 1 1 d . . . C19 C 0.2640(8) 0.7550(6) 0.7506(4) 0.0270(13) Uani 1 1 d . A . H19A H 0.3704 0.7703 0.7658 0.032 Uiso 1 1 calc R . . C20 C 0.2449(9) 0.6797(6) 0.6916(5) 0.0349(16) Uani 1 1 d . . . C21 C 0.0848(9) 0.6612(7) 0.6644(5) 0.0408(17) Uani 1 1 d . A . H21A H 0.0674 0.6142 0.6222 0.049 Uiso 1 1 calc R . . C22 C -0.0477(9) 0.7137(7) 0.7013(5) 0.0440(18) Uani 1 1 d . . . H22A H -0.1536 0.7007 0.6840 0.053 Uiso 1 1 calc R A . C23 C -0.0219(8) 0.7863(6) 0.7645(5) 0.0366(16) Uani 1 1 d . A . H23A H -0.1109 0.8192 0.7900 0.044 Uiso 1 1 calc R . . C25 C 0.1555(9) 0.8903(7) 0.8509(5) 0.0130(14) Uiso 0.704(5) 1 d P A 1 C25' C 0.151(2) 0.9424(16) 0.9007(12) 0.0130(14) Uiso 0.296(5) 1 d P A 2 C26 C 0.4665(8) 0.2837(6) 0.6716(5) 0.0379(17) Uani 1 1 d . . . H26A H 0.3686 0.3240 0.6788 0.045 Uiso 1 1 calc R . . C27 C 0.5056(9) 0.1759(7) 0.7340(5) 0.0445(19) Uani 1 1 d . . . H27A H 0.4350 0.1441 0.7824 0.053 Uiso 1 1 calc R . . C28 C 0.6496(9) 0.1153(7) 0.7243(5) 0.0444(19) Uani 1 1 d . . . H28A H 0.6778 0.0426 0.7664 0.053 Uiso 1 1 calc R . . C29 C 0.7527(8) 0.1636(6) 0.6512(5) 0.0310(15) Uani 1 1 d . . . C30 C 0.7056(7) 0.2739(6) 0.5917(5) 0.0306(15) Uani 1 1 d . . . H30A H 0.7752 0.3084 0.5434 0.037 Uiso 1 1 calc R . . C31 C 1.0351(9) 0.1438(7) 0.5922(5) 0.0418(18) Uani 1 1 d . . . C32 C 1.1691(9) 0.0484(7) 0.5980(5) 0.0444(19) Uani 1 1 d . . . H32A H 1.1207 -0.0285 0.5937 0.053 Uiso 1 1 calc R . . H32B H 1.2207 0.0348 0.6575 0.053 Uiso 1 1 calc R . . C33 C 1.2993(8) 0.0827(6) 0.5244(5) 0.0410(18) Uani 1 1 d . . . H33A H 1.3484 0.1596 0.5282 0.049 Uiso 1 1 calc R . . H33B H 1.2491 0.0949 0.4646 0.049 Uiso 1 1 calc R . . C34 C 1.4317(8) -0.0169(6) 0.5347(5) 0.0383(17) Uani 1 1 d . . . H34A H 1.4772 -0.0321 0.5958 0.046 Uiso 1 1 calc R . . H34B H 1.3827 -0.0926 0.5281 0.046 Uiso 1 1 calc R . . C87 C 0.3803(9) 0.6176(6) 0.6535(4) 0.0302(15) Uani 1 1 d . A . O1W O 0.2466(8) 1.0519(6) 0.9917(5) 0.0333(14) Uiso 0.704(5) 1 d P A 1 O1W' O 0.2189(18) 1.0742(14) 1.0457(11) 0.0333(14) Uiso 0.296(5) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.027(3) 0.039(3) 0.039(3) -0.017(3) -0.002(3) 0.008(2) C1 0.026(4) 0.051(5) 0.042(4) -0.019(4) 0.003(3) 0.007(3) Co1 0.0205(6) 0.0348(7) 0.0341(7) -0.0209(6) 0.0000(5) 0.0084(5) N2 0.034(3) 0.036(3) 0.037(3) 0.001(3) 0.006(3) 0.012(3) O2W 0.038(3) 0.053(3) 0.066(4) -0.011(3) -0.003(3) -0.009(2) C2 0.029(4) 0.063(5) 0.048(5) -0.014(4) 0.010(3) 0.002(4) Co2 0.0185(6) 0.0258(6) 0.0301(7) -0.0143(5) 0.0015(5) 0.0059(5) C3 0.034(4) 0.041(4) 0.038(4) -0.006(3) 0.003(3) -0.002(3) O3 0.040(3) 0.038(3) 0.065(4) 0.008(3) 0.021(3) 0.012(2) O3W 0.074(5) 0.091(5) 0.112(6) -0.005(5) 0.019(4) -0.003(4) C4 0.027(3) 0.037(4) 0.037(4) -0.012(3) 0.002(3) 0.005(3) N5 0.025(3) 0.029(3) 0.035(3) -0.009(2) 0.001(2) 0.004(2) C5 0.027(3) 0.040(4) 0.031(4) -0.008(3) 0.003(3) 0.006(3) O5 0.066(4) 0.047(3) 0.043(3) -0.018(3) 0.006(3) 0.012(3) O6 0.037(3) 0.076(4) 0.058(4) -0.032(3) -0.002(3) 0.007(3) N6 0.031(3) 0.027(3) 0.060(4) 0.005(3) 0.012(3) 0.011(2) C6 0.055(4) 0.067(4) 0.052(4) 0.009(3) 0.013(3) 0.026(3) C7 0.037(4) 0.056(5) 0.057(5) 0.010(4) 0.014(4) 0.022(4) O7 0.053(3) 0.068(4) 0.062(4) -0.038(3) 0.014(3) -0.007(3) O8 0.040(3) 0.067(4) 0.070(4) -0.042(3) 0.007(3) 0.004(3) C8 0.032(4) 0.037(4) 0.042(4) -0.002(3) 0.006(3) 0.011(3) C9 0.031(4) 0.037(4) 0.039(4) -0.004(3) 0.004(3) 0.009(3) C18 0.048(4) 0.024(3) 0.030(4) -0.004(3) 0.002(3) 0.000(3) C19 0.034(3) 0.024(3) 0.023(3) -0.005(2) 0.005(3) 0.006(2) C20 0.043(4) 0.030(4) 0.030(4) -0.004(3) 0.002(3) 0.005(3) C21 0.041(4) 0.042(4) 0.043(4) -0.018(3) -0.003(3) 0.001(3) C22 0.031(4) 0.047(4) 0.057(5) -0.019(4) 0.000(3) 0.006(3) C23 0.029(4) 0.041(4) 0.041(4) -0.011(3) 0.006(3) 0.007(3) C26 0.025(3) 0.043(4) 0.047(4) -0.014(4) 0.006(3) 0.005(3) C27 0.038(4) 0.043(4) 0.047(5) 0.001(4) 0.016(4) -0.001(3) C28 0.034(4) 0.035(4) 0.057(5) 0.002(4) 0.008(4) 0.003(3) C29 0.026(3) 0.027(3) 0.040(4) -0.008(3) 0.003(3) 0.002(3) C30 0.023(3) 0.030(3) 0.039(4) -0.007(3) 0.008(3) 0.003(3) C31 0.036(4) 0.038(4) 0.042(4) 0.007(3) 0.010(3) 0.014(3) C32 0.036(4) 0.038(4) 0.052(5) 0.001(4) 0.012(4) 0.016(3) C33 0.033(4) 0.034(4) 0.052(5) -0.004(3) 0.010(3) 0.010(3) C34 0.035(4) 0.032(4) 0.046(4) -0.007(3) 0.007(3) 0.010(3) C87 0.046(4) 0.022(3) 0.022(3) -0.005(3) 0.004(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.333(9) . ? N1 C5 1.341(8) . ? N1 Co1 2.211(6) . ? C1 C2 1.374(10) . ? Co1 O8 2.074(5) . ? Co1 O8 2.074(5) 2_577 ? Co1 O1W 2.101(6) 2_577 ? Co1 O1W 2.101(6) . ? Co1 C25' 2.138(18) . ? Co1 C25' 2.138(18) 2_577 ? Co1 O1W' 2.170(15) 2_577 ? Co1 O1W' 2.170(15) . ? Co1 N1 2.211(6) 2_577 ? O1 C6 1.280(11) . ? O1' C6 1.40(2) . ? N2 C6 1.318(10) . ? N2 C4 1.426(8) . ? O2W Co2 2.129(5) . ? C2 C3 1.383(10) . ? Co2 O5 2.075(5) . ? Co2 O5 2.075(5) 2_666 ? Co2 O2W 2.129(5) 2_666 ? Co2 N5 2.166(5) . ? Co2 N5 2.166(5) 2_666 ? C3 C4 1.385(9) . ? O3 C31 1.233(8) . ? C4 C5 1.385(9) . ? N5 C30 1.337(8) . ? N5 C26 1.344(8) . ? O5 C87 1.220(8) . ? O6 C87 1.306(8) . ? N6 C31 1.356(9) . ? N6 C29 1.400(8) . ? C6 C7 1.505(10) . ? C7 C8 1.511(10) . ? O7 C25 1.286(9) . ? O7 C25' 1.370(19) . ? O8 C25' 1.013(18) . ? O8 C25 1.222(9) . ? C8 C9 1.522(9) . ? C9 C9 1.523(13) 2_767 ? C18 C19 1.369(9) . ? C18 C23 1.417(10) . ? C18 C25 1.457(10) . ? C19 C20 1.375(9) . ? C20 C21 1.407(10) . ? C20 C87 1.479(9) . ? C21 C22 1.396(10) . ? C22 C23 1.410(10) . ? C26 C27 1.373(10) . ? C27 C28 1.372(10) . ? C28 C29 1.388(9) . ? C29 C30 1.391(9) . ? C31 C32 1.504(9) . ? C32 C33 1.513(9) . ? C33 C34 1.522(9) . ? C34 C34 1.509(13) 2_856 ? 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 C1 N1 C5 118.4(6) . . ? C1 N1 Co1 121.1(4) . . ? C5 N1 Co1 120.5(5) . . ? N1 C1 C2 122.9(6) . . ? O8 Co1 O8 179.999(2) . 2_577 ? O8 Co1 O1W 89.8(2) . 2_577 ? O8 Co1 O1W 90.2(2) 2_577 2_577 ? O8 Co1 O1W 90.2(2) . . ? O8 Co1 O1W 89.8(2) 2_577 . ? O1W Co1 O1W 180.0 2_577 . ? O8 Co1 C25' 27.8(5) . . ? O8 Co1 C25' 152.2(5) 2_577 . ? O1W Co1 C25' 117.5(5) 2_577 . ? O1W Co1 C25' 62.5(5) . . ? O8 Co1 C25' 152.2(5) . 2_577 ? O8 Co1 C25' 27.8(5) 2_577 2_577 ? O1W Co1 C25' 62.5(5) 2_577 2_577 ? O1W Co1 C25' 117.5(5) . 2_577 ? C25' Co1 C25' 180.000(6) . 2_577 ? O8 Co1 O1W' 65.0(5) . 2_577 ? O8 Co1 O1W' 115.0(5) 2_577 2_577 ? O1W Co1 O1W' 25.1(4) 2_577 2_577 ? O1W Co1 O1W' 154.9(4) . 2_577 ? C25' Co1 O1W' 92.8(7) . 2_577 ? C25' Co1 O1W' 87.2(7) 2_577 2_577 ? O8 Co1 O1W' 115.0(5) . . ? O8 Co1 O1W' 65.0(5) 2_577 . ? O1W Co1 O1W' 154.9(4) 2_577 . ? O1W Co1 O1W' 25.1(4) . . ? C25' Co1 O1W' 87.2(7) . . ? C25' Co1 O1W' 92.8(7) 2_577 . ? O1W' Co1 O1W' 179.999(2) 2_577 . ? O8 Co1 N1 90.6(2) . . ? O8 Co1 N1 89.4(2) 2_577 . ? O1W Co1 N1 89.5(2) 2_577 . ? O1W Co1 N1 90.5(2) . . ? C25' Co1 N1 89.2(5) . . ? C25' Co1 N1 90.8(5) 2_577 . ? O1W' Co1 N1 93.6(4) 2_577 . ? O1W' Co1 N1 86.4(4) . . ? O8 Co1 N1 89.4(2) . 2_577 ? O8 Co1 N1 90.6(2) 2_577 2_577 ? O1W Co1 N1 90.5(2) 2_577 2_577 ? O1W Co1 N1 89.5(2) . 2_577 ? C25' Co1 N1 90.8(5) . 2_577 ? C25' Co1 N1 89.2(5) 2_577 2_577 ? O1W' Co1 N1 86.4(4) 2_577 2_577 ? O1W' Co1 N1 93.6(4) . 2_577 ? N1 Co1 N1 179.999(2) . 2_577 ? C6 N2 C4 128.3(6) . . ? C1 C2 C3 119.2(7) . . ? O5 Co2 O5 179.999(2) . 2_666 ? O5 Co2 O2W 89.1(2) . . ? O5 Co2 O2W 90.9(2) 2_666 . ? O5 Co2 O2W 90.9(2) . 2_666 ? O5 Co2 O2W 89.1(2) 2_666 2_666 ? O2W Co2 O2W 179.999(1) . 2_666 ? O5 Co2 N5 91.2(2) . . ? O5 Co2 N5 88.8(2) 2_666 . ? O2W Co2 N5 93.5(2) . . ? O2W Co2 N5 86.5(2) 2_666 . ? O5 Co2 N5 88.8(2) . 2_666 ? O5 Co2 N5 91.2(2) 2_666 2_666 ? O2W Co2 N5 86.5(2) . 2_666 ? O2W Co2 N5 93.5(2) 2_666 2_666 ? N5 Co2 N5 179.999(1) . 2_666 ? C2 C3 C4 118.4(7) . . ? C3 C4 C5 119.1(6) . . ? C3 C4 N2 117.5(6) . . ? C5 C4 N2 123.3(6) . . ? C30 N5 C26 118.1(6) . . ? C30 N5 Co2 119.7(4) . . ? C26 N5 Co2 122.2(4) . . ? N1 C5 C4 122.1(6) . . ? C87 O5 Co2 135.3(5) . . ? C31 N6 C29 129.2(6) . . ? O1 C6 N2 115.5(8) . . ? O1 C6 O1' 56.6(9) . . ? N2 C6 O1' 117.6(10) . . ? O1 C6 C7 119.3(8) . . ? N2 C6 C7 117.1(7) . . ? O1' C6 C7 117.1(11) . . ? C6 C7 C8 114.1(6) . . ? C25 O7 C25' 46.6(8) . . ? C25' O8 C25 55.3(11) . . ? C25' O8 Co1 79.6(11) . . ? C25 O8 Co1 134.7(5) . . ? C7 C8 C9 111.9(6) . . ? C8 C9 C9 112.9(7) . 2_767 ? C19 C18 C23 116.8(6) . . ? C19 C18 C25 126.8(7) . . ? C23 C18 C25 116.5(6) . . ? C18 C19 C20 125.4(7) . . ? C19 C20 C21 117.7(6) . . ? C19 C20 C87 124.8(7) . . ? C21 C20 C87 117.5(6) . . ? C22 C21 C20 119.7(7) . . ? C21 C22 C23 120.4(7) . . ? C22 C23 C18 120.0(6) . . ? O8 C25 O7 123.0(7) . . ? O8 C25 C18 119.9(7) . . ? O7 C25 C18 117.0(6) . . ? O8 C25' O7 134.8(17) . . ? O8 C25' Co1 72.6(10) . . ? O7 C25' Co1 152.5(13) . . ? N5 C26 C27 122.2(6) . . ? C28 C27 C26 119.6(7) . . ? C27 C28 C29 119.4(7) . . ? C28 C29 C30 117.6(6) . . ? C28 C29 N6 119.3(6) . . ? C30 C29 N6 123.1(6) . . ? N5 C30 C29 123.1(6) . . ? O3 C31 N6 122.3(6) . . ? O3 C31 C32 123.7(6) . . ? N6 C31 C32 113.9(6) . . ? C31 C32 C33 114.1(6) . . ? C32 C33 C34 111.4(6) . . ? C34 C34 C33 113.0(7) 2_856 . ? O5 C87 O6 121.8(6) . . ? O5 C87 C20 121.4(7) . . ? O6 C87 C20 116.8(6) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.561 _refine_diff_density_min -0.804 _refine_diff_density_rms 0.131 _database_code_depnum_ccdc_archive 'CCDC 931960' ####################################################################### # # 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_compound-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H22 Co N3 O8' _chemical_formula_sum 'C17 H22 Co N3 O8' _chemical_formula_weight 455.31 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0708(11) _cell_length_b 10.1621(12) _cell_length_c 11.7772(14) _cell_angle_alpha 99.457(2) _cell_angle_beta 106.621(2) _cell_angle_gamma 108.491(2) _cell_volume 946.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.804 _exptl_absorpt_correction_T_max 0.858 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4845 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3323 _reflns_number_gt 2585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+-0.0500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3306 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Co1 Co 0.25526(5) 0.21823(4) 0.63171(4) 0.02060(15) Uani 1 1 d . . . O1 O 0.1955(3) 0.6474(3) 0.8693(2) 0.0422(7) Uani 1 1 d . . . N1 N 0.2918(3) 0.2794(3) 0.8255(2) 0.0239(6) Uani 1 1 d . . . C1 C 0.2458(4) 0.3856(3) 0.8656(3) 0.0269(7) Uani 1 1 d . . . H1A H 0.1922 0.4237 0.8080 0.032 Uiso 1 1 calc R . . O1W O 0.0085(3) 0.2008(2) 0.5891(2) 0.0309(6) Uani 1 1 d . . . H1WA H 0.020(5) 0.282(4) 0.594(3) 0.037 Uiso 1 1 d . . . H1WB H -0.0656(2) 0.15161(17) 0.51683(15) 0.037 Uiso 1 1 d . . . O2 O 0.4717(2) 1.16005(17) 0.66970(15) 0.0269(5) Uani 1 1 d . . . N2 N 0.2286(2) 0.55427(17) 1.03216(15) 0.0297(7) Uani 1 1 d . . . H2A H 0.2203 0.5623 1.1037 0.036 Uiso 1 1 calc R . . C2 C 0.2744(4) 0.4415(3) 0.9894(3) 0.0246(7) Uani 1 1 d . . . O2W O -0.0576(4) 0.6362(3) 0.6602(3) 0.0373(6) Uani 1 1 d . . . H2WA H 0.009(5) 0.650(5) 0.723(4) 0.053(15) Uiso 1 1 d . . . H2WB H -0.037(6) 0.590(5) 0.602(4) 0.078(17) Uiso 1 1 d . . . C3 C 0.3513(4) 0.3820(4) 1.0748(3) 0.0293(8) Uani 1 1 d . . . H3A H 0.3727 0.4168 1.1584 0.035 Uiso 1 1 calc R . . O3 O 0.2223(3) 0.9964(2) 0.62244(19) 0.0256(5) Uani 1 1 d . . . O3W O -0.2236(4) 0.3902(4) 0.7249(3) 0.0727(11) Uani 1 1 d . . . H3WA H -0.312(6) 0.345(6) 0.689(5) 0.087 Uiso 1 1 d . . . H3WB H -0.13003(19) 0.41228(16) 0.71654(14) 0.087 Uiso 1 1 d . . . N3 N 0.80249(19) 0.84787(16) 0.57886(14) 0.0253(6) Uani 1 1 d . . . H3B H 0.8588 0.9306 0.5730 0.030 Uiso 1 1 calc . . . H3C H 0.8349 0.7775 0.5679 0.030 Uiso 1 1 calc . . . O4 O 0.14496(19) 0.48556(16) 0.60022(14) 0.0272(5) Uani 1 1 d . . . C4 C 0.39533(19) 0.27074(16) 1.03343(14) 0.0319(8) Uani 1 1 d . . . H4A H 0.4450 0.2281 1.0888 0.038 Uiso 1 1 calc . . . C5 C 0.3651(4) 0.2226(4) 0.9087(3) 0.0304(8) Uani 1 1 d . . . H5A H 0.3969 0.1482 0.8819 0.037 Uiso 1 1 calc R . . O5 O 0.3684(3) 0.4262(2) 0.63546(19) 0.0235(5) Uani 1 1 d . . . C6 C 0.1961(4) 0.6519(4) 0.9740(3) 0.0290(8) Uani 1 1 d . . . C7 C 0.1642(5) 0.7691(4) 1.0476(3) 0.0354(9) Uani 1 1 d . . . H7A H 0.2694 0.8390 1.1085 0.043 Uiso 1 1 calc R . . H7B H 0.0946 0.7266 1.0916 0.043 Uiso 1 1 calc R . . C8 C 0.0797(5) 0.8467(4) 0.9679(3) 0.0364(9) Uani 1 1 d . . . H8A H -0.0249 0.7765 0.9065 0.044 Uiso 1 1 calc R . . H8B H 0.1499 0.8899 0.9246 0.044 Uiso 1 1 calc R . . C9 C 0.0454(5) 0.9639(4) 1.0412(3) 0.0344(8) Uani 1 1 d . . . H9A H 0.1503 1.0366 1.1003 0.041 Uiso 1 1 calc R . . H9B H -0.0213 0.9218 1.0871 0.041 Uiso 1 1 calc R . . C10 C 0.4038(4) 0.6633(3) 0.6216(3) 0.0193(7) Uani 1 1 d . . . C11 C 0.3464(4) 0.7748(3) 0.6339(3) 0.0223(7) Uani 1 1 d . . . H11A H 0.2425 0.7572 0.6403 0.027 Uiso 1 1 calc R . . C12 C 0.4447(4) 0.9123(3) 0.6366(3) 0.0202(7) Uani 1 1 d . . . C13 C 0.5996(4) 0.9401(3) 0.6252(3) 0.0220(7) Uani 1 1 d . . . H13A H 0.6661 1.0332 0.6297 0.026 Uiso 1 1 calc R . . C14 C 0.6545(4) 0.8273(3) 0.6070(3) 0.0207(7) Uani 1 1 d . . . C15 C 0.5577(4) 0.6897(3) 0.6090(3) 0.0212(7) Uani 1 1 d . . . H15A H 0.5968 0.6156 0.6019 0.025 Uiso 1 1 calc R . . C16 C 0.2965(4) 0.5143(3) 0.6187(3) 0.0201(7) Uani 1 1 d . . . C17 C 0.3781(4) 1.0296(3) 0.6437(3) 0.0218(7) 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 0.0241(3) 0.0143(2) 0.0273(3) 0.00841(18) 0.01011(19) 0.01030(19) O1 0.0631(19) 0.0484(16) 0.0312(14) 0.0163(12) 0.0175(13) 0.0391(15) N1 0.0275(15) 0.0199(14) 0.0270(15) 0.0083(12) 0.0093(13) 0.0122(13) C1 0.033(2) 0.0264(18) 0.0267(18) 0.0121(15) 0.0120(15) 0.0148(16) O1W 0.0280(13) 0.0277(13) 0.0352(14) 0.0042(12) 0.0083(11) 0.0135(12) O2 0.0300(13) 0.0156(12) 0.0387(14) 0.0096(10) 0.0133(11) 0.0115(11) N2 0.0436(19) 0.0294(16) 0.0239(15) 0.0096(13) 0.0156(14) 0.0198(15) C2 0.0255(18) 0.0224(17) 0.0287(18) 0.0093(14) 0.0120(15) 0.0096(15) O2W 0.0445(17) 0.0440(17) 0.0339(16) 0.0148(13) 0.0143(15) 0.0283(14) C3 0.032(2) 0.033(2) 0.0254(18) 0.0113(15) 0.0111(16) 0.0136(17) O3 0.0251(13) 0.0186(12) 0.0357(13) 0.0077(10) 0.0101(10) 0.0125(10) O3W 0.054(2) 0.083(3) 0.048(2) 0.0153(18) 0.0167(17) -0.0143(19) N3 0.0291(16) 0.0202(14) 0.0384(16) 0.0156(12) 0.0189(13) 0.0148(13) O4 0.0254(13) 0.0223(12) 0.0383(14) 0.0118(10) 0.0132(11) 0.0117(10) C4 0.036(2) 0.037(2) 0.0304(19) 0.0173(17) 0.0105(16) 0.0222(18) C5 0.032(2) 0.0298(19) 0.037(2) 0.0118(16) 0.0147(17) 0.0175(17) O5 0.0272(12) 0.0151(11) 0.0314(13) 0.0101(10) 0.0105(10) 0.0103(10) C6 0.0245(19) 0.033(2) 0.0286(19) 0.0054(16) 0.0065(15) 0.0139(16) C7 0.044(2) 0.032(2) 0.035(2) 0.0062(17) 0.0152(18) 0.0213(18) C8 0.045(2) 0.035(2) 0.040(2) 0.0134(17) 0.0188(18) 0.0230(19) C9 0.043(2) 0.030(2) 0.037(2) 0.0094(17) 0.0170(18) 0.0196(18) C10 0.0267(18) 0.0151(15) 0.0185(16) 0.0083(13) 0.0067(14) 0.0105(14) C11 0.0269(18) 0.0181(16) 0.0253(17) 0.0085(13) 0.0088(14) 0.0123(14) C12 0.0267(18) 0.0161(16) 0.0200(16) 0.0062(13) 0.0082(14) 0.0107(14) C13 0.0281(18) 0.0160(16) 0.0243(17) 0.0082(13) 0.0096(14) 0.0101(14) C14 0.0193(17) 0.0204(17) 0.0210(16) 0.0054(13) 0.0051(14) 0.0080(14) C15 0.0290(18) 0.0183(16) 0.0230(17) 0.0091(13) 0.0098(14) 0.0157(15) C16 0.033(2) 0.0148(16) 0.0179(16) 0.0074(13) 0.0116(14) 0.0127(15) C17 0.0283(19) 0.0200(17) 0.0222(17) 0.0092(14) 0.0103(14) 0.0133(15) _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 O5 2.023(2) . ? Co1 O1W 2.090(2) . ? Co1 O3 2.158(2) 1_545 ? Co1 N1 2.162(2) . ? Co1 O2 2.1735(17) 1_545 ? Co1 N3 2.3156(16) 2_666 ? Co1 C17 2.507(3) 1_545 ? O1 C6 1.225(4) . ? N1 C1 1.339(4) . ? N1 C5 1.339(4) . ? C1 C2 1.391(4) . ? O2 C17 1.255(4) . ? O2 Co1 2.1735(17) 1_565 ? N2 C6 1.355(4) . ? N2 C2 1.404(3) . ? C2 C3 1.388(4) . ? C3 C4 1.376(3) . ? O3 C17 1.280(4) . ? O3 Co1 2.158(2) 1_565 ? N3 C14 1.433(3) . ? N3 Co1 2.3156(16) 2_666 ? O4 C16 1.255(3) . ? C4 C5 1.386(3) . ? O5 C16 1.273(3) . ? C6 C7 1.509(4) . ? C7 C8 1.519(4) . ? C8 C9 1.520(4) . ? C9 C9 1.523(6) 2_577 ? C10 C15 1.392(4) . ? C10 C11 1.392(4) . ? C10 C16 1.507(4) . ? C11 C12 1.388(4) . ? C12 C13 1.393(4) . ? C12 C17 1.499(4) . ? C13 C14 1.397(4) . ? C14 C15 1.403(4) . ? C17 Co1 2.507(3) 1_565 ? 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 O5 Co1 O1W 100.70(9) . . ? O5 Co1 O3 158.20(8) . 1_545 ? O1W Co1 O3 100.16(9) . 1_545 ? O5 Co1 N1 91.86(9) . . ? O1W Co1 N1 88.88(9) . . ? O3 Co1 N1 94.81(8) 1_545 . ? O5 Co1 O2 98.44(8) . 1_545 ? O1W Co1 O2 160.80(8) . 1_545 ? O3 Co1 O2 60.64(7) 1_545 1_545 ? N1 Co1 O2 92.06(8) . 1_545 ? O5 Co1 N3 88.73(7) . 2_666 ? O1W Co1 N3 87.15(7) . 2_666 ? O3 Co1 N3 86.05(7) 1_545 2_666 ? N1 Co1 N3 176.03(8) . 2_666 ? O2 Co1 N3 91.74(6) 1_545 2_666 ? O5 Co1 C17 127.90(9) . 1_545 ? O1W Co1 C17 130.82(10) . 1_545 ? O3 Co1 C17 30.71(9) 1_545 1_545 ? N1 Co1 C17 95.85(9) . 1_545 ? O2 Co1 C17 30.04(9) 1_545 1_545 ? N3 Co1 C17 86.87(8) 2_666 1_545 ? C1 N1 C5 118.1(3) . . ? C1 N1 Co1 117.9(2) . . ? C5 N1 Co1 124.0(2) . . ? N1 C1 C2 123.1(3) . . ? C17 O2 Co1 89.87(16) . 1_565 ? C6 N2 C2 127.6(2) . . ? C3 C2 C1 118.2(3) . . ? C3 C2 N2 118.5(3) . . ? C1 C2 N2 123.3(3) . . ? C4 C3 C2 118.8(3) . . ? C17 O3 Co1 89.90(17) . 1_565 ? C14 N3 Co1 112.12(14) . 2_666 ? C3 C4 C5 119.6(2) . . ? N1 C5 C4 122.3(3) . . ? C16 O5 Co1 125.3(2) . . ? O1 C6 N2 122.4(3) . . ? O1 C6 C7 122.0(3) . . ? N2 C6 C7 115.6(3) . . ? C6 C7 C8 112.9(3) . . ? C7 C8 C9 113.3(3) . . ? C8 C9 C9 112.3(4) . 2_577 ? C15 C10 C11 119.7(3) . . ? C15 C10 C16 120.7(3) . . ? C11 C10 C16 119.6(3) . . ? C12 C11 C10 119.9(3) . . ? C11 C12 C13 120.9(3) . . ? C11 C12 C17 119.3(3) . . ? C13 C12 C17 119.7(3) . . ? C12 C13 C14 119.6(3) . . ? C13 C14 C15 119.3(3) . . ? C13 C14 N3 120.9(3) . . ? C15 C14 N3 119.7(2) . . ? C10 C15 C14 120.6(3) . . ? O4 C16 O5 124.8(3) . . ? O4 C16 C10 118.7(2) . . ? O5 C16 C10 116.5(3) . . ? O2 C17 O3 119.2(3) . . ? O2 C17 C12 121.4(3) . . ? O3 C17 C12 119.5(3) . . ? O2 C17 Co1 60.09(14) . 1_565 ? O3 C17 Co1 59.39(14) . 1_565 ? C12 C17 Co1 174.1(2) . 1_565 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.580 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 904984' ####################################################################### # # 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_compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 Cu N4 O6' _chemical_formula_sum 'C26 H26 Cu N4 O6' _chemical_formula_weight 554.05 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 6.9130(6) _cell_length_b 25.018(2) _cell_length_c 14.4591(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.337(2) _cell_angle_gamma 90.00 _cell_volume 2485.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_absorpt_coefficient_mu 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.815 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7251 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2550 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+2.9324P] 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 2531 _refine_ls_number_parameters 169 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.009 _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 C1 C -0.2626(4) 0.49674(11) 0.3682(2) 0.0473(6) Uani 1 1 d . . . H1 H -0.3588 0.5197 0.3415 0.057 Uiso 1 1 calc R . . C2 C -0.3021(5) 0.46346(12) 0.4393(2) 0.0585(8) Uani 1 1 d . . . H2 H -0.4240 0.4644 0.4608 0.070 Uiso 1 1 calc R . . C3 C -0.1626(5) 0.42884(12) 0.4788(2) 0.0566(8) Uani 1 1 d . . . H3 H -0.1883 0.4069 0.5278 0.068 Uiso 1 1 calc R . . C4 C 0.0173(4) 0.42695(10) 0.44464(17) 0.0448(6) Uani 1 1 d . A . C5 C 0.0492(4) 0.46204(10) 0.37317(17) 0.0401(6) Uani 1 1 d . . . H5 H 0.1693 0.4614 0.3498 0.048 Uiso 1 1 calc R . . C6 C 0.2979(5) 0.36762(11) 0.4366(2) 0.0527(7) Uani 1 1 d . A . C7 C 0.4293(6) 0.32923(13) 0.4944(2) 0.0720(10) Uani 1 1 d U . . H7AA H 0.5123 0.3501 0.5393 0.086 Uiso 0.502(5) 1 calc PR A 1 H7AB H 0.3479 0.3071 0.5292 0.086 Uiso 0.502(5) 1 calc PR A 1 H7BC H 0.3550 0.2985 0.5112 0.086 Uiso 0.498(5) 1 calc PR A 2 H7BD H 0.4849 0.3466 0.5511 0.086 Uiso 0.498(5) 1 calc PR A 2 C8 C 0.5419(13) 0.2973(3) 0.4518(6) 0.0654(10) Uani 0.502(5) 1 d PU A 1 H8A H 0.6202 0.3183 0.4136 0.078 Uiso 0.502(5) 1 calc PR A 1 H8B H 0.4621 0.2731 0.4115 0.078 Uiso 0.502(5) 1 calc PR A 1 C8' C 0.6106(13) 0.3090(3) 0.4311(7) 0.0654(10) Uani 0.498(5) 1 d PU A 2 H8'A H 0.5540 0.2866 0.3804 0.078 Uiso 0.498(5) 1 calc PR A 2 H8'B H 0.6645 0.3403 0.4037 0.078 Uiso 0.498(5) 1 calc PR A 2 C9 C 0.6742(11) 0.2653(3) 0.5221(5) 0.0654(10) Uani 0.502(5) 1 d P . 1 H9A H 0.7378 0.2894 0.5684 0.078 Uiso 0.502(5) 1 calc PR A 1 H9B H 0.5960 0.2405 0.5538 0.078 Uiso 0.502(5) 1 calc PR A 1 C9' C 0.7836(11) 0.2770(3) 0.4882(5) 0.0654(10) Uani 0.498(5) 1 d P . 2 H9'A H 0.8920 0.2739 0.4513 0.078 Uiso 0.498(5) 1 calc PR A 2 H9'B H 0.8279 0.2962 0.5448 0.078 Uiso 0.498(5) 1 calc PR A 2 C11 C 0.3980(3) 0.66796(9) 0.24336(16) 0.0337(5) Uani 1 1 d . . . C13 C 0.2995(4) 0.71640(10) 0.2350(2) 0.0461(6) Uani 1 1 d . . . H13 H 0.1643 0.7166 0.2243 0.055 Uiso 1 1 calc R . . C14 C 0.3992(4) 0.76437(11) 0.2422(2) 0.0554(7) Uani 1 1 d . . . H14 H 0.3314 0.7965 0.2367 0.067 Uiso 1 1 calc R . . C17 C 0.2843(3) 0.61719(9) 0.24871(16) 0.0329(5) Uani 1 1 d . . . N1 N -0.0860(3) 0.49658(8) 0.33674(14) 0.0369(5) Uani 1 1 d . . . N2 N 0.1615(4) 0.39169(9) 0.48390(16) 0.0569(7) Uani 1 1 d . . . H2A H 0.1642 0.3847 0.5423 0.068 Uiso 1 1 calc R A . O1 O 0.3115(3) 0.37690(9) 0.35575(15) 0.0645(6) Uani 1 1 d . . . O2 O 0.3276(2) 0.58529(7) 0.31302(12) 0.0415(4) Uani 1 1 d . . . O4 O 0.1355(2) 0.61038(7) 0.18789(11) 0.0365(4) Uani 1 1 d . . . Cu1 Cu 0.0000 0.551747(15) 0.2500 0.03139(14) Uani 1 2 d S . . 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 C1 0.0433(14) 0.0468(15) 0.0537(17) -0.0021(13) 0.0142(12) -0.0044(12) C2 0.0599(18) 0.0572(18) 0.064(2) -0.0018(15) 0.0324(16) -0.0118(15) C3 0.084(2) 0.0454(16) 0.0441(16) 0.0029(13) 0.0248(16) -0.0132(15) C4 0.0690(18) 0.0366(13) 0.0296(13) -0.0030(10) 0.0090(12) -0.0048(13) C5 0.0466(14) 0.0404(14) 0.0346(13) 0.0008(10) 0.0094(11) 0.0001(11) C6 0.074(2) 0.0358(14) 0.0447(17) -0.0009(12) -0.0080(14) 0.0001(13) C7 0.094(3) 0.0523(19) 0.064(2) 0.0112(15) -0.0172(18) 0.0066(17) C8 0.072(3) 0.051(2) 0.071(3) 0.0101(19) 0.0003(19) 0.011(2) C8' 0.072(3) 0.051(2) 0.071(3) 0.0101(19) 0.0003(19) 0.011(2) C9 0.072(3) 0.051(2) 0.071(3) 0.0101(19) 0.0003(19) 0.011(2) C9' 0.072(3) 0.051(2) 0.071(3) 0.0101(19) 0.0003(19) 0.011(2) C11 0.0319(12) 0.0356(12) 0.0336(12) 0.0005(10) 0.0034(9) 0.0003(9) C13 0.0375(13) 0.0440(15) 0.0578(17) 0.0054(12) 0.0099(12) 0.0079(11) C14 0.0629(17) 0.0365(15) 0.069(2) 0.0052(13) 0.0174(16) 0.0102(12) C17 0.0269(11) 0.0390(13) 0.0338(13) -0.0021(10) 0.0076(9) 0.0005(9) N1 0.0414(11) 0.0367(11) 0.0339(11) -0.0005(8) 0.0101(9) -0.0019(9) N2 0.0898(19) 0.0475(14) 0.0326(12) 0.0092(10) 0.0031(12) 0.0069(13) O1 0.0850(16) 0.0631(14) 0.0452(12) 0.0074(10) 0.0068(11) 0.0238(12) O2 0.0389(9) 0.0455(10) 0.0397(10) 0.0096(8) 0.0022(8) -0.0031(8) O4 0.0312(8) 0.0429(9) 0.0350(9) 0.0016(7) 0.0018(7) -0.0038(7) Cu1 0.0296(2) 0.0343(2) 0.0307(2) 0.000 0.00547(15) 0.000 _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 C1 N1 1.349(3) . ? C1 C2 1.373(4) . ? C1 H1 0.9300 . ? C2 C3 1.373(5) . ? C2 H2 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.392(4) . ? C4 N2 1.403(4) . ? C5 N1 1.338(3) . ? C5 H5 0.9300 . ? C6 O1 1.205(3) . ? C6 N2 1.365(4) . ? C6 C7 1.509(4) . ? C7 C8 1.315(9) . ? C7 C8' 1.708(10) . ? C7 H7AA 0.9700 . ? C7 H7AB 0.9700 . ? C7 H7BC 0.9700 . ? C7 H7BD 0.9700 . ? C8 C9 1.518(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8' C9' 1.593(10) . ? C8' H8'A 0.9700 . ? C8' H8'B 0.9700 . ? C9 C9 1.498(15) 7_656 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9' C9' 1.479(14) 7_656 ? C9' H9'A 0.9700 . ? C9' H9'B 0.9700 . ? C11 C13 1.389(3) . ? C11 C11 1.402(5) 2_655 ? C11 C17 1.500(3) . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 C14 1.387(6) 2_655 ? C14 H14 0.9300 . ? C17 O2 1.237(3) . ? C17 O4 1.289(3) . ? N1 Cu1 1.999(2) . ? N2 H2A 0.8600 . ? O4 Cu1 2.0055(16) . ? Cu1 N1 1.999(2) 2 ? Cu1 O4 2.0054(16) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 120.9(3) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 120.3(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 117.6(3) . . ? C3 C4 N2 120.1(3) . . ? C5 C4 N2 122.2(3) . . ? N1 C5 C4 122.6(2) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? O1 C6 N2 122.2(3) . . ? O1 C6 C7 123.6(3) . . ? N2 C6 C7 114.2(3) . . ? C8 C7 C6 118.6(5) . . ? C8 C7 C8' 20.3(5) . . ? C6 C7 C8' 108.9(4) . . ? C8 C7 H7AA 107.7 . . ? C6 C7 H7AA 107.7 . . ? C8' C7 H7AA 95.9 . . ? C8 C7 H7AB 107.7 . . ? C6 C7 H7AB 107.7 . . ? C8' C7 H7AB 127.7 . . ? H7AA C7 H7AB 107.1 . . ? C8 C7 H7BC 89.6 . . ? C6 C7 H7BC 109.9 . . ? C8' C7 H7BC 109.9 . . ? H7AA C7 H7BC 123.2 . . ? H7AB C7 H7BC 20.5 . . ? C8 C7 H7BD 117.9 . . ? C6 C7 H7BD 109.9 . . ? C8' C7 H7BD 109.9 . . ? H7AA C7 H7BD 16.7 . . ? H7AB C7 H7BD 90.9 . . ? H7BC C7 H7BD 108.3 . . ? C7 C8 C9 110.6(7) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C9' C8' C7 115.1(6) . . ? C9' C8' H8'A 108.5 . . ? C7 C8' H8'A 108.5 . . ? C9' C8' H8'B 108.5 . . ? C7 C8' H8'B 108.5 . . ? H8'A C8' H8'B 107.5 . . ? C9 C9 C8 112.4(8) 7_656 . ? C9 C9 H9A 109.1 7_656 . ? C8 C9 H9A 109.1 . . ? C9 C9 H9B 109.1 7_656 . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C9' C9' C8' 110.0(7) 7_656 . ? C9' C9' H9'A 109.7 7_656 . ? C8' C9' H9'A 109.7 . . ? C9' C9' H9'B 109.7 7_656 . ? C8' C9' H9'B 109.7 . . ? H9'A C9' H9'B 108.2 . . ? C13 C11 C11 119.22(15) . 2_655 ? C13 C11 C17 119.3(2) . . ? C11 C11 C17 121.16(12) 2_655 . ? C14 C13 C11 121.0(2) . . ? C14 C13 H13 119.5 . . ? C11 C13 H13 119.5 . . ? C13 C14 C14 119.74(16) . 2_655 ? C13 C14 H14 120.1 . . ? C14 C14 H14 120.1 2_655 . ? O2 C17 O4 122.4(2) . . ? O2 C17 C11 120.0(2) . . ? O4 C17 C11 117.4(2) . . ? C5 N1 C1 119.2(2) . . ? C5 N1 Cu1 116.72(16) . . ? C1 N1 Cu1 123.55(18) . . ? C6 N2 C4 125.0(2) . . ? C6 N2 H2A 117.5 . . ? C4 N2 H2A 117.5 . . ? C17 O4 Cu1 99.69(14) . . ? N1 Cu1 N1 92.67(12) 2 . ? N1 Cu1 O4 166.41(7) 2 2 ? N1 Cu1 O4 92.18(8) . 2 ? N1 Cu1 O4 92.18(8) 2 . ? N1 Cu1 O4 166.41(7) . . ? O4 Cu1 O4 85.99(10) 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.8(5) . . . . ? C1 C2 C3 C4 -1.5(5) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C2 C3 C4 N2 -179.8(3) . . . . ? C3 C4 C5 N1 -0.4(4) . . . . ? N2 C4 C5 N1 -178.5(2) . . . . ? O1 C6 C7 C8 -12.2(7) . . . . ? N2 C6 C7 C8 168.3(5) . . . . ? O1 C6 C7 C8' 7.3(5) . . . . ? N2 C6 C7 C8' -172.2(4) . . . . ? C6 C7 C8 C9 175.3(5) . . . . ? C8' C7 C8 C9 110(2) . . . . ? C8 C7 C8' C9' -68.5(17) . . . . ? C6 C7 C8' C9' 169.2(5) . . . . ? C7 C8 C9 C9 -171.2(9) . . . 7_656 ? C7 C8' C9' C9' 71.7(10) . . . 7_656 ? C11 C11 C13 C14 -1.9(5) 2_655 . . . ? C17 C11 C13 C14 171.3(3) . . . . ? C11 C13 C14 C14 0.3(6) . . . 2_655 ? C13 C11 C17 O2 -127.5(3) . . . . ? C11 C11 C17 O2 45.6(4) 2_655 . . . ? C13 C11 C17 O4 48.2(3) . . . . ? C11 C11 C17 O4 -138.7(3) 2_655 . . . ? C4 C5 N1 C1 -1.9(4) . . . . ? C4 C5 N1 Cu1 170.16(19) . . . . ? C2 C1 N1 C5 2.5(4) . . . . ? C2 C1 N1 Cu1 -169.0(2) . . . . ? O1 C6 N2 C4 3.6(5) . . . . ? C7 C6 N2 C4 -176.9(3) . . . . ? C3 C4 N2 C6 148.0(3) . . . . ? C5 C4 N2 C6 -34.0(4) . . . . ? O2 C17 O4 Cu1 12.3(3) . . . . ? C11 C17 O4 Cu1 -163.29(16) . . . . ? C5 N1 Cu1 N1 58.72(16) . . . 2 ? C1 N1 Cu1 N1 -129.6(2) . . . 2 ? C5 N1 Cu1 O4 -133.99(18) . . . 2 ? C1 N1 Cu1 O4 37.7(2) . . . 2 ? C5 N1 Cu1 O4 -52.1(4) . . . . ? C1 N1 Cu1 O4 119.6(3) . . . . ? C17 O4 Cu1 N1 -104.26(14) . . . 2 ? C17 O4 Cu1 N1 6.6(4) . . . . ? C17 O4 Cu1 O4 89.23(14) . . . 2 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.625 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 901805' ####################################################################### # # 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_compound5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H34 Cu N4 O10' _chemical_formula_sum 'C26 H34 Cu N4 O10' _chemical_formula_weight 626.12 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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.258(2) _cell_length_b 9.5904(11) _cell_length_c 18.920(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.346(2) _cell_angle_gamma 90.00 _cell_volume 2881.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 26.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 0.819 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15430 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5659 _reflns_number_gt 3874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+1.3212P] 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 5647 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _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 C1 C 0.0891(2) 0.2677(4) 0.2711(2) 0.0551(11) Uani 1 1 d . . . H1 H 0.1166 0.2104 0.3084 0.066 Uiso 1 1 calc R . . C2 C 0.0024(3) 0.2669(5) 0.2530(3) 0.0728(15) Uani 1 1 d . . . H2 H -0.0279 0.2106 0.2783 0.087 Uiso 1 1 calc R . . C3 C -0.0392(2) 0.3490(4) 0.1976(2) 0.0516(10) Uani 1 1 d . . . H3 H -0.0977 0.3481 0.1846 0.062 Uiso 1 1 calc R . . C4 C 0.00693(19) 0.4333(3) 0.16128(17) 0.0298(7) Uani 1 1 d . . . C5 C 0.09383(19) 0.4293(3) 0.18286(17) 0.0300(7) Uani 1 1 d . . . H5 H 0.1254 0.4858 0.1587 0.036 Uiso 1 1 calc R . . C6 C -0.0032(2) 0.6166(3) 0.06710(18) 0.0307(7) Uani 1 1 d . . . C7 C -0.0681(2) 0.6886(3) 0.00980(18) 0.0342(8) Uani 1 1 d . . . H7A H -0.1126 0.7239 0.0318 0.041 Uiso 1 1 calc R . . H7B H -0.0929 0.6208 -0.0266 0.041 Uiso 1 1 calc R . . C8 C -0.0325(2) 0.8088(3) -0.02704(18) 0.0347(8) Uani 1 1 d . . . H8A H 0.0196 0.7789 -0.0395 0.042 Uiso 1 1 calc R . . H8B H -0.0720 0.8316 -0.0717 0.042 Uiso 1 1 calc R . . C9 C -0.0154(2) 0.9395(3) 0.01950(18) 0.0353(8) Uani 1 1 d . . . H9A H -0.0668 0.9669 0.0341 0.042 Uiso 1 1 calc R . . H9B H 0.0264 0.9184 0.0629 0.042 Uiso 1 1 calc R . . C10 C 0.5263(2) -0.4385(3) 0.4926(2) 0.0407(9) Uani 1 1 d . . . H10A H 0.5648 -0.4696 0.4631 0.049 Uiso 1 1 calc R . . H10B H 0.5597 -0.4049 0.5381 0.049 Uiso 1 1 calc R . . C11 C 0.4733(2) -0.3186(3) 0.4541(2) 0.0431(9) Uani 1 1 d . . . H11A H 0.4390 -0.3522 0.4089 0.052 Uiso 1 1 calc R . . H11B H 0.4357 -0.2856 0.4840 0.052 Uiso 1 1 calc R . . C12 C 0.5275(2) -0.1987(3) 0.4386(2) 0.0476(10) Uani 1 1 d . . . H12A H 0.5636 -0.2316 0.4074 0.057 Uiso 1 1 calc R . . H12B H 0.5634 -0.1683 0.4837 0.057 Uiso 1 1 calc R . . C13 C 0.4767(2) -0.0749(4) 0.4028(2) 0.0418(9) Uani 1 1 d . . . C14 C 0.4123(2) 0.1939(3) 0.32837(17) 0.0319(7) Uani 1 1 d . . . H14 H 0.3715 0.1298 0.3346 0.038 Uiso 1 1 calc R . . C15 C 0.49651(19) 0.1609(3) 0.35401(17) 0.0312(7) Uani 1 1 d . . . C16 C 0.5562(2) 0.2574(4) 0.3445(2) 0.0482(10) Uani 1 1 d . . . H16 H 0.6132 0.2392 0.3615 0.058 Uiso 1 1 calc R . . C17 C 0.5305(2) 0.3815(4) 0.3095(2) 0.0554(11) Uani 1 1 d . . . H17 H 0.5700 0.4469 0.3020 0.067 Uiso 1 1 calc R . . C18 C 0.4462(2) 0.4067(4) 0.28597(19) 0.0418(9) Uani 1 1 d . . . H18 H 0.4291 0.4908 0.2630 0.050 Uiso 1 1 calc R . . C19 C 0.25719(18) 0.1173(3) 0.03713(16) 0.0254(7) Uani 1 1 d . . . H19 H 0.2703 0.2118 0.0383 0.031 Uiso 1 1 calc R . . C20 C 0.25015(18) 0.0443(3) -0.02731(16) 0.0254(7) Uani 1 1 d . . . C21 C 0.2316(2) -0.0976(3) -0.02829(18) 0.0323(7) Uani 1 1 d . . . H21 H 0.2282 -0.1488 -0.0706 0.039 Uiso 1 1 calc R . . C22 C 0.2181(2) -0.1624(3) 0.03344(18) 0.0361(8) Uani 1 1 d . . . H22 H 0.2048 -0.2568 0.0323 0.043 Uiso 1 1 calc R . . C23 C 0.2242(2) -0.0880(3) 0.09651(18) 0.0353(8) Uani 1 1 d . . . H23 H 0.2142 -0.1324 0.1376 0.042 Uiso 1 1 calc R . . C24 C 0.24527(18) 0.0532(3) 0.09961(16) 0.0265(7) Uani 1 1 d . . . C25 C 0.25104(19) 0.1332(3) 0.16844(16) 0.0297(7) Uani 1 1 d . . . C26 C 0.25910(19) 0.3810(3) 0.40551(17) 0.0308(7) Uani 1 1 d . . . N1 N 0.13468(16) 0.3484(3) 0.23663(13) 0.0304(6) Uani 1 1 d . . . N2 N 0.38750(16) 0.3149(3) 0.29489(13) 0.0298(6) Uani 1 1 d . . . N3 N -0.03635(16) 0.5171(3) 0.10482(14) 0.0328(6) Uani 1 1 d . . . H3A H -0.0899 0.5046 0.0924 0.039 Uiso 1 1 calc R . . N4 N 0.52397(16) 0.0343(3) 0.38904(15) 0.0383(7) Uani 1 1 d . . . H4 H 0.5775 0.0251 0.4036 0.046 Uiso 1 1 calc R . . O1 O 0.26323(13) 0.2660(2) 0.16617(11) 0.0330(5) Uani 1 1 d . . . O1W O 0.27844(15) 0.5751(2) 0.21746(13) 0.0455(6) Uani 1 1 d . . . H1WA H 0.2761 0.6349 0.2501 0.055 Uiso 1 1 d R . . H1WB H 0.2392 0.5906 0.1807 0.055 Uiso 1 1 d R . . O2 O 0.24419(16) 0.0739(2) 0.22500(12) 0.0436(6) Uani 1 1 d . . . O3 O 0.26095(14) 0.4557(2) 0.35063(11) 0.0352(5) Uani 1 1 d . . . O4 O 0.26256(16) 0.2509(2) 0.40491(12) 0.0459(6) Uani 1 1 d . . . O5 O 0.07130(14) 0.6426(2) 0.07901(14) 0.0496(7) Uani 1 1 d . . . O6 O 0.40002(16) -0.0731(3) 0.38878(18) 0.0713(9) Uani 1 1 d . . . Cu1 Cu 0.26215(2) 0.35270(4) 0.261831(19) 0.02712(12) Uani 1 1 d . . . O2W O 0.29465(14) 0.4956(2) 0.08107(12) 0.0436(6) Uani 1 1 d . . . H2WA H 0.2706 0.5006 0.0366 0.052 Uiso 1 1 d R . . H2WB H 0.2810 0.4196 0.0987 0.052 Uiso 1 1 d R . . O3W O 0.22241(14) -0.0088(2) 0.43218(13) 0.0476(6) Uani 1 1 d . . . H3WA H 0.2444 -0.0623 0.4055 0.057 Uiso 1 1 d R . . H3WB H 0.2356 0.0753 0.4255 0.057 Uiso 1 1 d R . . O4W O 0.25613(17) -0.1805(3) 0.29639(16) 0.0634(8) Uani 1 1 d . . . H4WA H 0.3071 -0.1802 0.3194 0.076 Uiso 1 1 d R . . H4WB H 0.2467 -0.1082 0.2699 0.076 Uiso 1 1 d 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 C1 0.043(2) 0.067(3) 0.052(2) 0.033(2) 0.0043(19) 0.001(2) C2 0.043(2) 0.092(3) 0.081(3) 0.060(3) 0.010(2) -0.008(2) C3 0.034(2) 0.063(3) 0.056(2) 0.025(2) 0.0048(18) -0.0070(19) C4 0.0334(18) 0.0243(17) 0.0314(18) 0.0020(14) 0.0059(14) -0.0002(14) C5 0.0312(18) 0.0283(17) 0.0310(18) 0.0028(14) 0.0077(14) -0.0015(14) C6 0.0334(19) 0.0200(17) 0.0383(19) 0.0036(13) 0.0066(15) 0.0048(14) C7 0.0340(19) 0.0255(17) 0.041(2) 0.0069(14) 0.0029(15) 0.0037(14) C8 0.040(2) 0.0275(18) 0.0359(19) 0.0059(14) 0.0068(15) 0.0054(15) C9 0.039(2) 0.0264(18) 0.041(2) 0.0070(15) 0.0111(16) 0.0046(15) C10 0.036(2) 0.0293(19) 0.053(2) 0.0093(16) 0.0015(17) 0.0016(15) C11 0.037(2) 0.033(2) 0.056(2) 0.0091(17) 0.0023(17) 0.0031(15) C12 0.039(2) 0.032(2) 0.068(3) 0.0135(18) 0.0026(19) 0.0046(16) C13 0.034(2) 0.034(2) 0.053(2) 0.0080(17) -0.0003(17) 0.0047(16) C14 0.0322(18) 0.0282(17) 0.0347(19) 0.0023(14) 0.0059(14) 0.0005(14) C15 0.0318(18) 0.0273(17) 0.0340(18) 0.0016(14) 0.0063(14) 0.0048(14) C16 0.030(2) 0.045(2) 0.068(3) 0.012(2) 0.0064(18) 0.0023(17) C17 0.040(2) 0.042(2) 0.084(3) 0.020(2) 0.012(2) -0.0050(18) C18 0.043(2) 0.0337(19) 0.048(2) 0.0132(17) 0.0080(18) 0.0031(16) C19 0.0252(16) 0.0242(16) 0.0267(16) -0.0029(13) 0.0051(13) -0.0022(12) C20 0.0242(16) 0.0273(17) 0.0251(16) 0.0012(13) 0.0065(13) 0.0025(13) C21 0.0381(19) 0.0277(17) 0.0320(18) -0.0046(14) 0.0097(15) 0.0014(14) C22 0.048(2) 0.0199(17) 0.041(2) 0.0012(14) 0.0120(16) 0.0013(15) C23 0.049(2) 0.0287(18) 0.0300(19) 0.0058(14) 0.0123(16) 0.0029(15) C24 0.0272(17) 0.0262(17) 0.0263(17) 0.0006(13) 0.0061(13) 0.0056(13) C25 0.0314(17) 0.0328(19) 0.0243(17) 0.0008(14) 0.0047(13) 0.0022(14) C26 0.0320(18) 0.036(2) 0.0243(17) -0.0010(14) 0.0053(14) -0.0006(14) N1 0.0306(14) 0.0320(15) 0.0270(14) 0.0049(12) 0.0026(11) 0.0013(12) N2 0.0359(15) 0.0255(14) 0.0280(15) 0.0022(11) 0.0065(12) 0.0039(12) N3 0.0259(14) 0.0324(15) 0.0378(16) 0.0094(12) 0.0015(12) -0.0002(12) N4 0.0250(15) 0.0336(16) 0.0526(19) 0.0063(14) -0.0002(13) 0.0038(12) O1 0.0442(14) 0.0298(13) 0.0251(12) -0.0012(10) 0.0072(10) 0.0001(10) O1W 0.0622(17) 0.0343(13) 0.0383(14) 0.0025(11) 0.0071(12) -0.0002(12) O2 0.0714(18) 0.0358(14) 0.0252(13) 0.0020(10) 0.0138(12) -0.0004(12) O3 0.0467(14) 0.0357(13) 0.0245(12) 0.0003(10) 0.0103(10) 0.0035(11) O4 0.0755(18) 0.0272(13) 0.0398(15) -0.0024(11) 0.0226(13) 0.0020(12) O5 0.0309(14) 0.0472(15) 0.0686(18) 0.0280(13) 0.0058(12) 0.0008(12) O6 0.0343(16) 0.0463(17) 0.125(3) 0.0354(17) -0.0019(16) 0.0011(13) Cu1 0.0333(2) 0.0264(2) 0.0210(2) 0.00232(16) 0.00434(15) 0.00477(17) O2W 0.0521(15) 0.0384(14) 0.0392(14) 0.0006(11) 0.0074(12) -0.0064(11) O3W 0.0508(15) 0.0374(14) 0.0588(17) -0.0022(12) 0.0213(13) -0.0015(12) O4W 0.0667(19) 0.0423(16) 0.075(2) 0.0123(14) 0.0022(15) 0.0011(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(4) . ? C1 C2 1.378(5) . ? C2 C3 1.368(5) . ? C3 C4 1.381(4) . ? C4 C5 1.385(4) . ? C4 N3 1.400(4) . ? C5 N1 1.338(4) . ? C6 O5 1.209(4) . ? C6 N3 1.370(4) . ? C6 C7 1.509(4) . ? C7 C8 1.524(4) . ? C8 C9 1.522(4) . ? C9 C9 1.517(6) 3_575 ? C10 C10 1.518(6) 3_646 ? C10 C11 1.525(4) . ? C11 C12 1.514(5) . ? C12 C13 1.520(5) . ? C13 O6 1.218(4) . ? C13 N4 1.357(4) . ? C14 N2 1.342(4) . ? C14 C15 1.388(4) . ? C15 C16 1.380(4) . ? C15 N4 1.410(4) . ? C16 C17 1.382(5) . ? C17 C18 1.370(5) . ? C18 N2 1.335(4) . ? C19 C24 1.382(4) . ? C19 C20 1.389(4) . ? C20 C21 1.393(4) . ? C20 C26 1.493(4) 4_565 ? C21 C22 1.381(4) . ? C22 C23 1.376(4) . ? C23 C24 1.395(4) . ? C24 C25 1.497(4) . ? C25 O2 1.238(3) . ? C25 O1 1.291(4) . ? C26 O4 1.249(4) . ? C26 O3 1.267(3) . ? C26 C20 1.493(4) 4_566 ? N1 Cu1 2.025(3) . ? N2 Cu1 2.032(3) . ? O1 Cu1 1.995(2) . ? O1W Cu1 2.328(2) . ? O3 Cu1 1.953(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.8(3) . . ? C3 C2 C1 120.0(3) . . ? C2 C3 C4 119.1(3) . . ? C3 C4 C5 117.8(3) . . ? C3 C4 N3 118.5(3) . . ? C5 C4 N3 123.7(3) . . ? N1 C5 C4 123.3(3) . . ? O5 C6 N3 122.5(3) . . ? O5 C6 C7 123.9(3) . . ? N3 C6 C7 113.6(3) . . ? C6 C7 C8 113.5(3) . . ? C9 C8 C7 113.5(3) . . ? C9 C9 C8 112.7(3) 3_575 . ? C10 C10 C11 113.0(3) 3_646 . ? C12 C11 C10 111.8(3) . . ? C11 C12 C13 113.3(3) . . ? O6 C13 N4 122.8(3) . . ? O6 C13 C12 122.8(3) . . ? N4 C13 C12 114.4(3) . . ? N2 C14 C15 122.4(3) . . ? C16 C15 C14 118.1(3) . . ? C16 C15 N4 118.6(3) . . ? C14 C15 N4 123.4(3) . . ? C15 C16 C17 119.4(3) . . ? C18 C17 C16 119.1(3) . . ? N2 C18 C17 122.4(3) . . ? C24 C19 C20 121.7(3) . . ? C19 C20 C21 118.8(3) . . ? C19 C20 C26 120.0(3) . 4_565 ? C21 C20 C26 121.2(3) . 4_565 ? C22 C21 C20 120.1(3) . . ? C23 C22 C21 120.3(3) . . ? C22 C23 C24 120.8(3) . . ? C19 C24 C23 118.3(3) . . ? C19 C24 C25 121.4(3) . . ? C23 C24 C25 120.2(3) . . ? O2 C25 O1 121.6(3) . . ? O2 C25 C24 121.1(3) . . ? O1 C25 C24 117.3(3) . . ? O4 C26 O3 123.3(3) . . ? O4 C26 C20 120.0(3) . 4_566 ? O3 C26 C20 116.7(3) . 4_566 ? C1 N1 C5 118.1(3) . . ? C1 N1 Cu1 122.9(2) . . ? C5 N1 Cu1 118.9(2) . . ? C18 N2 C14 118.6(3) . . ? C18 N2 Cu1 122.7(2) . . ? C14 N2 Cu1 118.7(2) . . ? C6 N3 C4 127.4(3) . . ? C13 N4 C15 128.3(3) . . ? C25 O1 Cu1 110.48(18) . . ? C26 O3 Cu1 115.2(2) . . ? O3 Cu1 O1 174.24(9) . . ? O3 Cu1 N1 90.85(10) . . ? O1 Cu1 N1 89.14(9) . . ? O3 Cu1 N2 91.10(10) . . ? O1 Cu1 N2 90.12(9) . . ? N1 Cu1 N2 167.72(10) . . ? O3 Cu1 O1W 82.50(9) . . ? O1 Cu1 O1W 91.78(8) . . ? N1 Cu1 O1W 97.08(9) . . ? N2 Cu1 O1W 95.19(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.387 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 901803' ####################################################################### # # 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_compound-6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C52 H68 Cu2 N10 O19' _chemical_formula_sum 'C52 H68 Cu2 N10 O19' _chemical_formula_weight 1264.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3258(13) _cell_length_b 15.6874(18) _cell_length_c 18.231(2) _cell_angle_alpha 67.240(2) _cell_angle_beta 76.216(2) _cell_angle_gamma 80.258(2) _cell_volume 2890.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.2 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320.0 _exptl_absorpt_coefficient_mu 0.818 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_process_details ; SADABS, Sheldrick, 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _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 15557 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.20 _reflns_number_total 10431 _reflns_number_gt 6364 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+1.2062P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10301 _refine_ls_number_parameters 737 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1157 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 1.80645(5) -0.29205(4) 0.24469(3) 0.03082(18) Uani 1 1 d . . . Cu2 Cu 1.23025(5) 0.22280(4) 0.26524(4) 0.03196(18) Uani 1 1 d . . . O1 O 1.7402(5) -0.4924(3) 0.5352(3) 0.0849(17) Uani 1 1 d . . . O2 O 1.7554(4) -1.0300(3) 0.9914(3) 0.0745(14) Uani 1 1 d . . . O3 O 1.6129(3) -0.3301(2) 0.3478(2) 0.0470(10) Uani 1 1 d . . . O4 O 1.2463(3) 0.0922(2) 0.3391(2) 0.0368(9) Uani 1 1 d . . . O5 O 1.3997(3) 0.0924(2) 0.2381(2) 0.0474(10) Uani 1 1 d . . . O6 O 1.9820(3) -0.2379(2) 0.1251(2) 0.0445(10) Uani 1 1 d . . . O7 O 1.6819(3) -0.1954(2) 0.2676(2) 0.0364(9) Uani 1 1 d . . . O8 O 2.2068(3) -0.6486(2) 0.1970(2) 0.0392(9) Uani 1 1 d . . . O9 O 1.9396(3) -0.3776(2) 0.21265(19) 0.0339(8) Uani 1 1 d . . . O10 O 0.8466(12) 0.0562(10) 0.3880(8) 0.067(2) Uiso 0.380(9) 1 d P A 1 O10A O 0.8133(14) 0.1190(11) 0.3651(9) 0.067(2) Uiso 0.310(5) 1 d P A 2 O10B O 0.8958(15) 0.0061(11) 0.3852(9) 0.067(2) Uiso 0.310(5) 1 d P A 2 O11 O 2.3731(3) -0.6402(2) 0.1001(2) 0.0503(10) Uani 1 1 d . . . O12 O 1.7629(5) 0.3847(4) 0.2861(3) 0.0961(19) Uani 1 1 d . . . N1 N 1.8897(4) -0.2918(3) 0.3298(2) 0.0339(10) Uani 1 1 d . . . N2 N 1.8981(4) -0.4299(3) 0.5450(2) 0.0406(11) Uani 1 1 d . . . H2 H 1.9459 -0.4344 0.5769 0.049 Uiso 1 1 calc R . . N3 N 1.6136(4) -1.1088(3) 0.9824(2) 0.0404(11) Uani 1 1 d . . . H3 H 1.5562 -1.1037 0.9571 0.049 Uiso 1 1 calc R . . N4 N 1.7156(4) -1.2894(3) 1.1626(2) 0.0341(10) Uani 1 1 d . . . N5 N 1.2295(4) -0.2423(3) 0.5285(3) 0.0585(15) Uani 1 1 d . . . H5A H 1.1666 -0.2127 0.5476 0.070 Uiso 1 1 calc R . . H5B H 1.2445 -0.3008 0.5535 0.070 Uiso 1 1 calc R . . N6 N 2.3630(4) -0.2953(3) -0.0723(2) 0.0387(11) Uani 1 1 d . . . H6A H 2.4242 -0.3207 -0.0972 0.046 Uiso 1 1 calc R . . H6B H 2.3453 -0.2363 -0.0916 0.046 Uiso 1 1 calc R . . N7 N 1.3529(4) 0.2570(3) 0.3113(3) 0.0372(11) Uani 1 1 d . . . N8 N 1.6651(4) 0.3192(3) 0.2308(3) 0.0455(12) Uani 1 1 d . . . H8C H 1.6722 0.3014 0.1908 0.055 Uiso 1 1 calc R . . N9 N 1.1289(4) 0.1851(3) 0.2075(3) 0.0336(10) Uani 1 1 d . . . N10 N 0.8620(5) 0.0526(4) 0.2621(3) 0.0585(14) Uani 1 1 d . . . H10C H 0.8212 0.0390 0.2345 0.070 Uiso 1 1 calc R B 1 C1 C 1.8683(5) -0.3581(3) 0.4041(3) 0.0353(12) Uani 1 1 d . . . H1 H 1.8171 -0.4032 0.4135 0.042 Uiso 1 1 calc R . . C2 C 1.9624(5) -0.2270(4) 0.3174(3) 0.0461(14) Uani 1 1 d . . . H2A H 1.9764 -0.1802 0.2666 0.055 Uiso 1 1 calc R . . C3 C 2.0168(6) -0.2268(4) 0.3761(4) 0.0566(17) Uani 1 1 d . . . H3A H 2.0668 -0.1803 0.3651 0.068 Uiso 1 1 calc R . . C4 C 1.9983(5) -0.2948(4) 0.4516(3) 0.0483(15) Uani 1 1 d . . . H4 H 2.0373 -0.2963 0.4916 0.058 Uiso 1 1 calc R . . C5 C 1.9199(5) -0.3615(3) 0.4669(3) 0.0348(12) Uani 1 1 d . . . C6 C 1.8102(5) -0.4892(4) 0.5750(3) 0.0457(14) Uani 1 1 d . . . C7 C 1.7997(5) -0.5500(4) 0.6637(3) 0.0446(14) Uani 1 1 d . . . H7A H 1.7678 -0.5119 0.6964 0.054 Uiso 1 1 calc R . . H7B H 1.8803 -0.5770 0.6744 0.054 Uiso 1 1 calc R . . C8 C 1.7172(5) -0.6274(4) 0.6889(3) 0.0504(15) Uani 1 1 d . . . H8A H 1.7397 -0.6581 0.6499 0.061 Uiso 1 1 calc R . . H8B H 1.6335 -0.6007 0.6879 0.061 Uiso 1 1 calc R . . C9 C 1.7247(5) -0.6992(4) 0.7733(3) 0.0440(14) Uani 1 1 d . . . H9A H 1.8097 -0.7152 0.7783 0.053 Uiso 1 1 calc R . . H9B H 1.6845 -0.6720 0.8134 0.053 Uiso 1 1 calc R . . C10 C 1.6661(5) -0.7873(4) 0.7912(3) 0.0464(14) Uani 1 1 d . . . H10A H 1.5786 -0.7733 0.7953 0.056 Uiso 1 1 calc R . . H10B H 1.6965 -0.8091 0.7465 0.056 Uiso 1 1 calc R . . C11 C 1.6921(5) -0.8639(4) 0.8691(3) 0.0456(14) Uani 1 1 d . . . H11A H 1.7796 -0.8745 0.8667 0.055 Uiso 1 1 calc R . . H11B H 1.6561 -0.8439 0.9143 0.055 Uiso 1 1 calc R . . C12 C 1.6422(5) -0.9542(4) 0.8838(3) 0.0464(14) Uani 1 1 d . . . H12A H 1.6737 -0.9717 0.8368 0.056 Uiso 1 1 calc R . . H12B H 1.5541 -0.9445 0.8900 0.056 Uiso 1 1 calc R . . C13 C 1.6755(5) -1.0331(4) 0.9585(3) 0.0441(14) Uani 1 1 d . . . C14 C 1.6325(4) -1.1948(3) 1.0441(3) 0.0325(12) Uani 1 1 d . . . C15 C 1.6975(5) -1.2067(3) 1.1035(3) 0.0362(12) Uani 1 1 d . . . H15A H 1.7300 -1.1556 1.1025 0.043 Uiso 1 1 calc R . . C16 C 1.6685(5) -1.3623(4) 1.1646(3) 0.0482(15) Uani 1 1 d . . . H16 H 1.6810 -1.4195 1.2051 0.058 Uiso 1 1 calc R . . C17 C 1.6015(6) -1.3557(4) 1.1082(4) 0.0560(17) Uani 1 1 d . . . H17 H 1.5679 -1.4075 1.1114 0.067 Uiso 1 1 calc R . . C18 C 1.5849(5) -1.2715(4) 1.0473(3) 0.0476(15) Uani 1 1 d . . . H18 H 1.5415 -1.2665 1.0083 0.057 Uiso 1 1 calc R . . C19 C 1.4630(4) -0.0994(3) 0.3154(3) 0.0290(11) Uani 1 1 d . . . H19 H 1.5156 -0.0675 0.2684 0.035 Uiso 1 1 calc R . . C20 C 1.4877(4) -0.1932(3) 0.3545(3) 0.0276(11) Uani 1 1 d . . . C21 C 1.4106(4) -0.2419(3) 0.4248(3) 0.0349(12) Uani 1 1 d . . . H21 H 1.4277 -0.3054 0.4504 0.042 Uiso 1 1 calc R . . C22 C 1.3069(5) -0.1957(3) 0.4572(3) 0.0383(13) Uani 1 1 d . . . C23 C 1.2837(5) -0.1013(3) 0.4163(3) 0.0383(13) Uani 1 1 d . . . H23 H 1.2147 -0.0701 0.4369 0.046 Uiso 1 1 calc R . . C24 C 1.3601(4) -0.0518(3) 0.3456(3) 0.0293(11) Uani 1 1 d . . . C25 C 1.3363(5) 0.0501(3) 0.3043(3) 0.0332(12) Uani 1 1 d . . . C26 C 1.5998(4) -0.2441(3) 0.3225(3) 0.0317(12) Uani 1 1 d . . . C27 C 2.1171(4) -0.3671(3) 0.1091(3) 0.0251(10) Uani 1 1 d . . . C28 C 2.1895(4) -0.3113(3) 0.0399(3) 0.0307(12) Uani 1 1 d . . . H28 H 2.1697 -0.2475 0.0200 0.037 Uiso 1 1 calc R . . C29 C 2.2921(4) -0.3504(3) -0.0001(3) 0.0280(11) Uani 1 1 d . . . C30 C 2.3202(4) -0.4458(3) 0.0314(3) 0.0317(12) Uani 1 1 d . . . H30 H 2.3880 -0.4726 0.0052 0.038 Uiso 1 1 calc R . . C31 C 2.2498(4) -0.5013(3) 0.1007(3) 0.0263(11) Uani 1 1 d . . . C32 C 2.1477(4) -0.4617(3) 0.1395(3) 0.0286(11) Uani 1 1 d . . . H32 H 2.0996 -0.4991 0.1862 0.034 Uiso 1 1 calc R . . C33 C 2.0068(4) -0.3230(3) 0.1497(3) 0.0298(11) Uani 1 1 d . . . C34 C 2.2814(5) -0.6046(3) 0.1340(3) 0.0334(12) Uani 1 1 d . . . C35 C 1.1497(5) 0.2114(3) 0.1266(3) 0.0407(13) Uani 1 1 d . . . H35 H 1.2144 0.2471 0.0958 0.049 Uiso 1 1 calc R . . C36 C 1.0779(5) 0.1870(4) 0.0881(3) 0.0477(15) Uani 1 1 d . . . H36 H 1.0937 0.2063 0.0318 0.057 Uiso 1 1 calc R . . C37 C 0.9823(5) 0.1339(4) 0.1334(3) 0.0470(14) Uani 1 1 d . . . H37 H 0.9332 0.1166 0.1082 0.056 Uiso 1 1 calc R A . C38 C 0.9601(5) 0.1067(4) 0.2165(3) 0.0418(13) Uani 1 1 d . . . C39 C 1.0362(5) 0.1327(3) 0.2517(3) 0.0417(14) Uani 1 1 d . . . H39 H 1.0228 0.1134 0.3079 0.050 Uiso 1 1 calc R A . C40 C 0.8238(18) 0.0196(13) 0.3419(12) 0.117(2) Uiso 0.668(16) 1 d P A 1 C41 C 0.7239(16) -0.0486(13) 0.3732(10) 0.117(2) Uiso 0.668(16) 1 d P A 1 H41A H 0.6783 -0.0335 0.3303 0.141 Uiso 0.668(16) 1 calc PR A 1 H41B H 0.7645 -0.1102 0.3811 0.141 Uiso 0.668(16) 1 calc PR A 1 C42 C 0.6315(14) -0.0542(11) 0.4508(9) 0.117(2) Uiso 0.668(16) 1 d PD A 1 H42A H 0.5768 -0.1008 0.4616 0.141 Uiso 0.668(16) 1 calc PR A 1 H42B H 0.6751 -0.0753 0.4953 0.141 Uiso 0.668(16) 1 calc PR A 1 C40' C 0.790(4) 0.061(3) 0.339(2) 0.117(2) Uiso 0.332(16) 1 d P A 2 C41' C 0.684(3) 0.004(3) 0.3676(17) 0.117(2) Uiso 0.332(16) 1 d PD A 2 H41C H 0.6218 0.0330 0.3351 0.141 Uiso 0.332(16) 1 calc PR A 2 H41D H 0.7096 -0.0577 0.3657 0.141 Uiso 0.332(16) 1 calc PR A 2 C42' C 0.639(3) -0.001(3) 0.4521(17) 0.117(2) Uiso 0.332(16) 1 d PD A 2 H42C H 0.6374 -0.0645 0.4898 0.141 Uiso 0.332(16) 1 calc PR A 2 H42D H 0.6892 0.0317 0.4673 0.141 Uiso 0.332(16) 1 calc PR A 2 C43 C 0.5607(9) 0.0287(7) 0.4502(6) 0.117(2) Uiso 1 1 d D . . H43A H 0.5241 0.0585 0.4025 0.141 Uiso 1 1 calc R A 1 H43B H 0.6063 0.0721 0.4560 0.141 Uiso 1 1 calc R A 1 C44 C 1.4645(5) 0.2690(3) 0.2679(3) 0.0388(13) Uani 1 1 d . . . H44 H 1.4859 0.2509 0.2233 0.047 Uiso 1 1 calc R . . C45 C 1.5518(5) 0.3072(4) 0.2854(3) 0.0390(13) Uani 1 1 d . . . C48 C 1.3244(5) 0.2780(4) 0.3785(4) 0.0493(15) Uani 1 1 d . . . H48 H 1.2476 0.2673 0.4111 0.059 Uiso 1 1 calc R . . C49 C 1.7637(5) 0.3551(4) 0.2335(4) 0.0495(15) Uani 1 1 d . . . C50 C 1.8708(5) 0.3572(4) 0.1670(3) 0.0472(15) Uani 1 1 d . . . H50A H 1.8616 0.3149 0.1420 0.057 Uiso 1 1 calc R . . H50B H 1.9442 0.3356 0.1899 0.057 Uiso 1 1 calc R . . C51 C 1.8854(5) 0.4538(4) 0.1023(3) 0.0414(13) Uani 1 1 d . . . H51A H 1.8103 0.4773 0.0816 0.050 Uiso 1 1 calc R . . H51B H 1.9005 0.4953 0.1264 0.050 Uiso 1 1 calc R . . C52 C 1.9901(5) 0.4528(3) 0.0325(3) 0.0391(13) Uani 1 1 d . . . H52A H 2.0645 0.4277 0.0538 0.047 Uiso 1 1 calc R . . H52B H 1.9740 0.4117 0.0084 0.047 Uiso 1 1 calc R . . C66 C 1.5212(5) 0.3316(5) 0.3533(4) 0.0579(17) Uani 1 1 d . . . H66 H 1.5761 0.3582 0.3670 0.070 Uiso 1 1 calc R . . C68 C 1.4063(6) 0.3150(5) 0.3998(4) 0.0635(19) Uani 1 1 d . . . H68 H 1.3839 0.3292 0.4466 0.076 Uiso 1 1 calc R . . O1W O 1.0606(4) 0.2560(3) 0.3541(2) 0.0630(13) Uani 1 1 d . . . H1WA H 1.0209 0.3087 0.3377 0.076 Uiso 1 1 d R . . H1WB H 1.0234 0.2160 0.3961 0.076 Uiso 1 1 d R . . O2W O 0.0543(4) 0.5563(3) 0.6575(2) 0.0588(11) Uani 1 1 d . . . H2WA H 0.0530 0.5116 0.7028 0.071 Uiso 1 1 d R . . H2WB H 0.1230 0.5699 0.6590 0.071 Uiso 1 1 d R . . O3W O 0.2346(4) 0.0230(3) 0.8300(2) 0.0554(11) Uani 1 1 d . . . H3WA H 0.2648 0.0736 0.7986 0.067 Uiso 1 1 d R . . H3WB H 0.1667 0.0345 0.8581 0.067 Uiso 1 1 d R . . O4W O 0.0016(4) 0.0568(3) 0.9102(4) 0.121(2) Uani 1 1 d . . . H4WA H 0.0009 0.1122 0.9076 0.145 Uiso 1 1 d R . . H4WB H -0.0565 0.0253 0.9423 0.145 Uiso 1 1 d R . . O5W O 0.9415(6) -0.0874(4) 0.5222(4) 0.139(3) Uani 1 1 d . . . H5WA H 0.9359 -0.0597 0.4727 0.166 Uiso 1 1 d R . . H5WB H 0.8996 -0.0590 0.5525 0.166 Uiso 1 1 d R . . O6W O 0.3586(9) 0.5363(4) 0.5746(4) 0.201(5) Uani 1 1 d . . . H6WA H 0.2950 0.5094 0.6033 0.241 Uiso 1 1 d R . . H6WB H 0.3288 0.5394 0.5349 0.241 Uiso 1 1 d R . . O7W O 0.4273(3) 0.8967(2) 0.8954(2) 0.0493(10) Uani 1 1 d . . . H7WA H 0.3760 0.9439 0.8840 0.059 Uiso 1 1 d R . . H7WB H 0.4711 0.9068 0.8485 0.059 Uiso 1 1 d 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 0.0319(4) 0.0310(3) 0.0250(3) -0.0093(3) -0.0047(3) 0.0062(3) Cu2 0.0294(3) 0.0262(3) 0.0376(4) -0.0109(3) -0.0025(3) -0.0024(2) O1 0.106(4) 0.103(4) 0.044(3) 0.009(3) -0.035(3) -0.060(3) O2 0.102(4) 0.048(3) 0.080(3) 0.000(2) -0.059(3) -0.024(2) O3 0.049(2) 0.031(2) 0.052(2) -0.0134(18) -0.007(2) 0.0107(17) O4 0.035(2) 0.0313(19) 0.043(2) -0.0169(17) -0.0024(17) 0.0027(15) O5 0.050(2) 0.033(2) 0.042(2) -0.0076(18) 0.008(2) 0.0017(17) O6 0.044(2) 0.0261(19) 0.055(2) -0.0140(17) 0.0012(19) 0.0022(16) O7 0.037(2) 0.036(2) 0.0313(19) -0.0111(16) -0.0020(17) 0.0007(16) O8 0.034(2) 0.0286(18) 0.049(2) -0.0103(17) -0.0045(18) -0.0006(15) O9 0.035(2) 0.0310(18) 0.0287(19) -0.0087(15) -0.0020(16) 0.0039(15) O11 0.044(2) 0.039(2) 0.060(3) -0.020(2) 0.000(2) 0.0094(18) O12 0.076(4) 0.164(5) 0.083(4) -0.079(4) 0.023(3) -0.072(4) N1 0.032(2) 0.037(2) 0.030(2) -0.014(2) -0.0011(19) 0.0031(19) N2 0.044(3) 0.049(3) 0.026(2) -0.007(2) -0.011(2) -0.008(2) N3 0.046(3) 0.043(3) 0.031(2) -0.006(2) -0.017(2) -0.005(2) N4 0.035(2) 0.032(2) 0.036(2) -0.018(2) -0.005(2) 0.0045(19) N5 0.046(3) 0.052(3) 0.055(3) -0.004(3) 0.011(3) -0.011(2) N6 0.039(3) 0.037(2) 0.031(2) -0.008(2) 0.003(2) -0.003(2) N7 0.032(3) 0.037(2) 0.038(3) -0.011(2) 0.001(2) -0.0064(19) N8 0.039(3) 0.066(3) 0.042(3) -0.031(2) 0.000(2) -0.015(2) N9 0.033(2) 0.030(2) 0.037(3) -0.013(2) -0.005(2) -0.0029(19) N10 0.058(3) 0.082(4) 0.044(3) -0.021(3) -0.010(3) -0.033(3) C1 0.043(3) 0.032(3) 0.030(3) -0.011(2) -0.009(2) 0.000(2) C2 0.052(4) 0.046(3) 0.033(3) -0.008(3) -0.005(3) -0.008(3) C3 0.075(5) 0.054(4) 0.046(4) -0.015(3) -0.010(3) -0.027(3) C4 0.054(4) 0.057(4) 0.037(3) -0.016(3) -0.012(3) -0.012(3) C5 0.044(3) 0.037(3) 0.024(3) -0.010(2) -0.009(2) -0.003(2) C6 0.055(4) 0.048(3) 0.030(3) -0.006(3) -0.009(3) -0.012(3) C7 0.053(4) 0.047(3) 0.029(3) -0.006(3) -0.011(3) -0.007(3) C8 0.052(4) 0.054(4) 0.039(3) -0.006(3) -0.013(3) -0.009(3) C9 0.053(4) 0.046(3) 0.032(3) -0.007(3) -0.013(3) -0.015(3) C10 0.049(4) 0.051(3) 0.036(3) -0.007(3) -0.011(3) -0.013(3) C11 0.046(3) 0.043(3) 0.046(3) -0.006(3) -0.021(3) -0.006(3) C12 0.060(4) 0.041(3) 0.037(3) -0.009(3) -0.017(3) -0.005(3) C13 0.056(4) 0.034(3) 0.042(3) -0.009(3) -0.020(3) -0.001(3) C14 0.028(3) 0.035(3) 0.033(3) -0.012(2) -0.007(2) 0.001(2) C15 0.039(3) 0.036(3) 0.034(3) -0.012(2) -0.009(3) -0.003(2) C16 0.062(4) 0.035(3) 0.047(4) -0.014(3) -0.016(3) 0.004(3) C17 0.080(5) 0.038(3) 0.063(4) -0.022(3) -0.030(4) -0.005(3) C18 0.054(4) 0.050(4) 0.046(3) -0.021(3) -0.023(3) 0.002(3) C19 0.031(3) 0.032(3) 0.021(2) -0.009(2) 0.000(2) -0.005(2) C20 0.029(3) 0.028(3) 0.025(3) -0.009(2) -0.003(2) -0.003(2) C21 0.036(3) 0.030(3) 0.039(3) -0.011(2) -0.009(3) -0.003(2) C22 0.038(3) 0.033(3) 0.039(3) -0.010(2) 0.001(3) -0.008(2) C23 0.030(3) 0.041(3) 0.044(3) -0.019(3) -0.001(3) 0.001(2) C24 0.030(3) 0.032(3) 0.029(3) -0.015(2) -0.006(2) -0.001(2) C25 0.033(3) 0.032(3) 0.040(3) -0.017(3) -0.010(3) -0.003(2) C26 0.033(3) 0.032(3) 0.034(3) -0.017(2) -0.008(2) 0.004(2) C27 0.029(3) 0.026(2) 0.025(3) -0.013(2) -0.004(2) -0.005(2) C28 0.037(3) 0.024(2) 0.033(3) -0.011(2) -0.009(2) 0.000(2) C29 0.026(3) 0.033(3) 0.024(3) -0.009(2) -0.002(2) -0.008(2) C30 0.025(3) 0.033(3) 0.039(3) -0.019(2) -0.001(2) -0.002(2) C31 0.025(3) 0.025(2) 0.031(3) -0.013(2) -0.007(2) 0.001(2) C32 0.030(3) 0.024(3) 0.027(3) -0.005(2) -0.001(2) -0.008(2) C33 0.030(3) 0.028(3) 0.036(3) -0.016(2) -0.010(2) 0.002(2) C34 0.034(3) 0.031(3) 0.035(3) -0.013(2) -0.007(3) 0.003(2) C35 0.039(3) 0.037(3) 0.045(3) -0.018(3) 0.001(3) -0.005(2) C36 0.059(4) 0.055(4) 0.035(3) -0.024(3) -0.006(3) -0.007(3) C37 0.053(4) 0.052(4) 0.044(3) -0.024(3) -0.010(3) -0.012(3) C38 0.045(3) 0.045(3) 0.041(3) -0.018(3) -0.006(3) -0.013(3) C39 0.045(3) 0.037(3) 0.039(3) -0.009(2) 0.000(3) -0.012(3) C44 0.039(3) 0.038(3) 0.038(3) -0.016(2) 0.000(3) -0.007(2) C45 0.032(3) 0.049(3) 0.037(3) -0.017(3) -0.004(3) -0.006(2) C48 0.034(3) 0.069(4) 0.047(4) -0.029(3) 0.004(3) -0.008(3) C49 0.045(4) 0.059(4) 0.048(4) -0.019(3) -0.001(3) -0.024(3) C50 0.038(3) 0.052(4) 0.051(4) -0.018(3) -0.002(3) -0.013(3) C51 0.037(3) 0.045(3) 0.045(3) -0.018(3) -0.007(3) -0.008(3) C52 0.037(3) 0.042(3) 0.042(3) -0.017(3) -0.007(3) -0.010(2) C66 0.043(4) 0.093(5) 0.054(4) -0.042(4) -0.008(3) -0.014(3) C68 0.048(4) 0.106(6) 0.058(4) -0.055(4) -0.004(3) -0.006(4) O1W 0.058(3) 0.050(2) 0.063(3) -0.018(2) 0.015(2) -0.001(2) O2W 0.060(3) 0.051(2) 0.062(3) -0.007(2) -0.025(2) -0.010(2) O3W 0.056(3) 0.045(2) 0.064(3) -0.017(2) -0.009(2) -0.0097(19) O4W 0.061(3) 0.049(3) 0.249(8) -0.052(4) -0.024(4) -0.009(2) O5W 0.132(5) 0.117(5) 0.094(4) -0.004(4) 0.028(4) 0.024(4) O6W 0.450(15) 0.082(5) 0.099(5) -0.021(4) -0.065(7) -0.112(7) O7W 0.050(2) 0.048(2) 0.041(2) -0.0094(18) -0.0060(19) -0.0016(18) _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 O9 1.979(3) . ? Cu1 O7 1.987(3) . ? Cu1 N4 1.992(4) 1_564 ? Cu1 N1 2.000(4) . ? Cu2 O8 1.929(3) 1_465 ? Cu2 O4 1.976(3) . ? Cu2 N9 2.016(4) . ? Cu2 N7 2.021(4) . ? Cu2 O1W 2.328(4) . ? O1 C6 1.213(7) . ? O2 C13 1.216(6) . ? O3 C26 1.240(6) . ? O4 C25 1.291(6) . ? O5 C25 1.241(6) . ? O6 C33 1.237(5) . ? O7 C26 1.287(6) . ? O8 C34 1.278(6) . ? O8 Cu2 1.929(3) 1_645 ? O9 C33 1.294(5) . ? O10 C40 1.28(2) . ? O10A C40' 1.26(4) . ? O10A O10B 1.80(2) . ? O10B C40' 1.57(4) . ? O11 C34 1.240(6) . ? O12 C49 1.215(7) . ? N1 C2 1.334(7) . ? N1 C1 1.347(6) . ? N2 C6 1.348(7) . ? N2 C5 1.407(6) . ? N2 H2 0.8600 . ? N3 C13 1.351(7) . ? N3 C14 1.405(6) . ? N3 H3 0.8600 . ? N4 C16 1.327(7) . ? N4 C15 1.348(6) . ? N4 Cu1 1.993(4) 1_546 ? N5 C22 1.389(6) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 C29 1.405(6) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N7 C44 1.322(6) . ? N7 C48 1.341(7) . ? N8 C49 1.351(7) . ? N8 C45 1.414(6) . ? N8 H8C 0.8600 . ? N9 C35 1.340(6) . ? N9 C39 1.342(6) . ? N10 C40 1.329(19) . ? N10 C38 1.407(7) . ? N10 C40' 1.49(4) . ? N10 H10C 0.8600 . ? C1 C5 1.384(7) . ? C1 H1 0.9300 . ? C2 C3 1.358(8) . ? C2 H2A 0.9300 . ? C3 C4 1.371(7) . ? C3 H3A 0.9300 . ? C4 C5 1.390(7) . ? C4 H4 0.9300 . ? C6 C7 1.514(7) . ? C7 C8 1.518(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.529(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.521(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.518(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.518(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.519(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C18 1.375(7) . ? C14 C15 1.389(7) . ? C15 H15A 0.9300 . ? C16 C17 1.380(8) . ? C16 H16 0.9300 . ? C17 C18 1.376(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.377(6) . ? C19 C24 1.392(6) . ? C19 H19 0.9300 . ? C20 C21 1.387(6) . ? C20 C26 1.501(6) . ? C21 C22 1.403(7) . ? C21 H21 0.9300 . ? C22 C23 1.387(7) . ? C23 C24 1.391(7) . ? C23 H23 0.9300 . ? C24 C25 1.488(7) . ? C27 C32 1.383(6) . ? C27 C28 1.388(6) . ? C27 C33 1.500(6) . ? C28 C29 1.400(6) . ? C28 H28 0.9300 . ? C29 C30 1.390(6) . ? C30 C31 1.376(6) . ? C30 H30 0.9300 . ? C31 C32 1.390(6) . ? C31 C34 1.506(6) . ? C32 H32 0.9300 . ? C35 C36 1.374(7) . ? C35 H35 0.9300 . ? C36 C37 1.377(7) . ? C36 H36 0.9300 . ? C37 C38 1.377(7) . ? C37 H37 0.9300 . ? C38 C39 1.380(7) . ? C39 H39 0.9300 . ? C40 C41 1.54(2) . ? C41 C42 1.527(19) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 C43 1.405(14) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C40' C41' 1.49(4) . ? C41' C42' 1.480(19) . ? C41' C43 1.91(3) . ? C41' H41C 0.9700 . ? C41' H41D 0.9700 . ? C42' C43 0.93(3) . ? C42' H42C 0.9700 . ? C42' H42D 0.9700 . ? C43 C43 1.991(19) 2_656 ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.392(7) . ? C44 H44 0.9300 . ? C45 C66 1.385(8) . ? C48 C68 1.371(8) . ? C48 H48 0.9300 . ? C49 C50 1.491(8) . ? C50 C51 1.525(7) . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C52 1.521(7) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 C52 1.510(9) 2_965 ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C66 C68 1.378(8) . ? C66 H66 0.9300 . ? C68 H68 0.9300 . ? O1W H1WA 0.8499 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8499 . ? O2W H2WB 0.8503 . ? O3W H3WA 0.8501 . ? O3W H3WB 0.8500 . ? O4W H4WA 0.8500 . ? O4W H4WB 0.8501 . ? O5W H5WA 0.8500 . ? O5W H5WB 0.8500 . ? O6W H6WA 0.8499 . ? O6W H6WB 0.8501 . ? O7W H7WA 0.8500 . ? O7W H7WB 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Cu1 O7 173.98(13) . . ? O9 Cu1 N4 91.72(15) . 1_564 ? O7 Cu1 N4 87.88(15) . 1_564 ? O9 Cu1 N1 91.19(15) . . ? O7 Cu1 N1 89.30(15) . . ? N4 Cu1 N1 177.00(16) 1_564 . ? O8 Cu2 O4 176.94(14) 1_465 . ? O8 Cu2 N9 91.10(16) 1_465 . ? O4 Cu2 N9 88.87(15) . . ? O8 Cu2 N7 89.25(16) 1_465 . ? O4 Cu2 N7 91.22(15) . . ? N9 Cu2 N7 171.64(17) . . ? O8 Cu2 O1W 85.56(14) 1_465 . ? O4 Cu2 O1W 91.39(14) . . ? N9 Cu2 O1W 93.18(16) . . ? N7 Cu2 O1W 95.18(16) . . ? C25 O4 Cu2 107.5(3) . . ? C26 O7 Cu1 102.4(3) . . ? C34 O8 Cu2 126.0(3) . 1_645 ? C33 O9 Cu1 103.5(3) . . ? C40' O10A O10B 58(2) . . ? C40' O10B O10A 43.3(15) . . ? C2 N1 C1 118.1(5) . . ? C2 N1 Cu1 123.1(4) . . ? C1 N1 Cu1 118.8(4) . . ? C6 N2 C5 126.6(5) . . ? C6 N2 H2 116.7 . . ? C5 N2 H2 116.7 . . ? C13 N3 C14 127.4(5) . . ? C13 N3 H3 116.3 . . ? C14 N3 H3 116.3 . . ? C16 N4 C15 118.7(5) . . ? C16 N4 Cu1 124.2(4) . 1_546 ? C15 N4 Cu1 117.0(3) . 1_546 ? C22 N5 H5A 120.0 . . ? C22 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C29 N6 H6A 120.0 . . ? C29 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C44 N7 C48 118.2(5) . . ? C44 N7 Cu2 117.7(4) . . ? C48 N7 Cu2 123.8(4) . . ? C49 N8 C45 128.3(5) . . ? C49 N8 H8C 115.9 . . ? C45 N8 H8C 115.9 . . ? C35 N9 C39 118.9(5) . . ? C35 N9 Cu2 122.4(4) . . ? C39 N9 Cu2 118.7(4) . . ? C40 N10 C38 128.9(10) . . ? C40 N10 C40' 27.6(15) . . ? C38 N10 C40' 121.6(16) . . ? C40 N10 H10C 115.6 . . ? C38 N10 H10C 115.6 . . ? C40' N10 H10C 114.9 . . ? N1 C1 C5 122.4(5) . . ? N1 C1 H1 118.8 . . ? C5 C1 H1 118.8 . . ? N1 C2 C3 122.5(5) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C2 C3 C4 120.3(6) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 118.4(6) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C1 C5 C4 118.3(5) . . ? C1 C5 N2 123.2(5) . . ? C4 C5 N2 118.5(5) . . ? O1 C6 N2 123.0(5) . . ? O1 C6 C7 121.2(5) . . ? N2 C6 C7 115.8(5) . . ? C6 C7 C8 112.6(5) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 112.8(5) . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 113.0(5) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 112.4(5) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 112.6(5) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 113.0(5) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? O2 C13 N3 122.8(5) . . ? O2 C13 C12 122.6(5) . . ? N3 C13 C12 114.5(5) . . ? C18 C14 C15 117.4(5) . . ? C18 C14 N3 119.8(5) . . ? C15 C14 N3 122.8(5) . . ? N4 C15 C14 122.7(5) . . ? N4 C15 H15A 118.6 . . ? C14 C15 H15A 118.6 . . ? N4 C16 C17 121.9(5) . . ? N4 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 119.2(5) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C14 C18 C17 120.1(5) . . ? C14 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C24 120.6(4) . . ? C20 C19 H19 119.7 . . ? C24 C19 H19 119.7 . . ? C19 C20 C21 120.5(4) . . ? C19 C20 C26 120.6(4) . . ? C21 C20 C26 118.9(4) . . ? C20 C21 C22 120.2(5) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 N5 120.5(5) . . ? C23 C22 C21 118.1(5) . . ? N5 C22 C21 121.4(5) . . ? C22 C23 C24 122.3(5) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C23 C24 C19 118.3(4) . . ? C23 C24 C25 121.5(4) . . ? C19 C24 C25 120.1(4) . . ? O5 C25 O4 121.6(4) . . ? O5 C25 C24 120.9(4) . . ? O4 C25 C24 117.5(4) . . ? O3 C26 O7 121.0(4) . . ? O3 C26 C20 121.3(4) . . ? O7 C26 C20 117.7(4) . . ? C32 C27 C28 119.8(4) . . ? C32 C27 C33 121.3(4) . . ? C28 C27 C33 119.0(4) . . ? C27 C28 C29 120.4(4) . . ? C27 C28 H28 119.8 . . ? C29 C28 H28 119.8 . . ? C30 C29 C28 118.6(4) . . ? C30 C29 N6 120.3(4) . . ? C28 C29 N6 121.1(4) . . ? C31 C30 C29 121.2(4) . . ? C31 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? C30 C31 C32 119.6(4) . . ? C30 C31 C34 120.6(4) . . ? C32 C31 C34 119.8(4) . . ? C27 C32 C31 120.3(4) . . ? C27 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? O6 C33 O9 121.2(4) . . ? O6 C33 C27 121.7(4) . . ? O9 C33 C27 117.1(4) . . ? O11 C34 O8 125.4(5) . . ? O11 C34 C31 120.1(4) . . ? O8 C34 C31 114.5(4) . . ? N9 C35 C36 121.7(5) . . ? N9 C35 H35 119.2 . . ? C36 C35 H35 119.2 . . ? C35 C36 C37 119.4(5) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C38 C37 C36 119.3(5) . . ? C38 C37 H37 120.3 . . ? C36 C37 H37 120.3 . . ? C37 C38 C39 118.5(5) . . ? C37 C38 N10 118.7(5) . . ? C39 C38 N10 122.8(5) . . ? N9 C39 C38 122.2(5) . . ? N9 C39 H39 118.9 . . ? C38 C39 H39 118.9 . . ? O10 C40 N10 122.3(16) . . ? O10 C40 C41 120.4(16) . . ? N10 C40 C41 115.6(16) . . ? C42 C41 C40 119.6(14) . . ? C42 C41 H41A 107.4 . . ? C40 C41 H41A 107.4 . . ? C42 C41 H41B 107.4 . . ? C40 C41 H41B 107.4 . . ? H41A C41 H41B 107.0 . . ? C43 C42 C41 115.9(12) . . ? C43 C42 H42A 108.3 . . ? C41 C42 H42A 108.3 . . ? C43 C42 H42B 108.3 . . ? C41 C42 H42B 108.3 . . ? H42A C42 H42B 107.4 . . ? O10A C40' N10 121(3) . . ? O10A C40' C41' 129(3) . . ? N10 C40' C41' 109(3) . . ? O10A C40' O10B 78(2) . . ? N10 C40' O10B 91(2) . . ? C41' C40' O10B 110(3) . . ? C42' C41' C40' 104(3) . . ? C42' C41' C43 28.5(15) . . ? C40' C41' C43 115(2) . . ? C42' C41' H41C 111.0 . . ? C40' C41' H41C 111.0 . . ? C43 C41' H41C 82.6 . . ? C42' C41' H41D 111.0 . . ? C40' C41' H41D 111.0 . . ? C43 C41' H41D 124.1 . . ? H41C C41' H41D 109.0 . . ? C43 C42' C41' 102(3) . . ? C43 C42' H42C 111.3 . . ? C41' C42' H42C 111.3 . . ? C43 C42' H42D 111.3 . . ? C41' C42' H42D 111.3 . . ? H42C C42' H42D 109.2 . . ? C42' C43 C42 37(2) . . ? C42' C43 C41' 49(2) . . ? C42 C43 C41' 50.0(12) . . ? C42' C43 C43 113(2) . 2_656 ? C42 C43 C43 96.3(10) . 2_656 ? C41' C43 C43 144.1(14) . 2_656 ? C42' C43 H43A 126.5 . . ? C42 C43 H43A 112.5 . . ? C41' C43 H43A 77.3 . . ? C43 C43 H43A 112.5 2_656 . ? C42' C43 H43B 75.6 . . ? C42 C43 H43B 112.5 . . ? C41' C43 H43B 94.3 . . ? C43 C43 H43B 112.5 2_656 . ? H43A C43 H43B 110.0 . . ? N7 C44 C45 123.7(5) . . ? N7 C44 H44 118.2 . . ? C45 C44 H44 118.2 . . ? C66 C45 C44 118.1(5) . . ? C66 C45 N8 125.2(5) . . ? C44 C45 N8 116.6(5) . . ? N7 C48 C68 121.2(5) . . ? N7 C48 H48 119.4 . . ? C68 C48 H48 119.4 . . ? O12 C49 N8 121.6(5) . . ? O12 C49 C50 123.0(5) . . ? N8 C49 C50 115.4(5) . . ? C49 C50 C51 112.8(5) . . ? C49 C50 H50A 109.0 . . ? C51 C50 H50A 109.0 . . ? C49 C50 H50B 109.0 . . ? C51 C50 H50B 109.0 . . ? H50A C50 H50B 107.8 . . ? C52 C51 C50 111.6(4) . . ? C52 C51 H51A 109.3 . . ? C50 C51 H51A 109.3 . . ? C52 C51 H51B 109.3 . . ? C50 C51 H51B 109.3 . . ? H51A C51 H51B 108.0 . . ? C52 C52 C51 113.7(5) 2_965 . ? C52 C52 H52A 108.8 2_965 . ? C51 C52 H52A 108.8 . . ? C52 C52 H52B 108.8 2_965 . ? C51 C52 H52B 108.8 . . ? H52A C52 H52B 107.7 . . ? C68 C66 C45 117.5(6) . . ? C68 C66 H66 121.3 . . ? C45 C66 H66 121.3 . . ? C48 C68 C66 121.2(6) . . ? C48 C68 H68 119.4 . . ? C66 C68 H68 119.4 . . ? Cu2 O1W H1WA 117.8 . . ? Cu2 O1W H1WB 125.2 . . ? H1WA O1W H1WB 114.9 . . ? H2WA O2W H2WB 91.3 . . ? H3WA O3W H3WB 109.5 . . ? H4WA O4W H4WB 117.8 . . ? H5WA O5W H5WB 113.1 . . ? H6WA O6W H6WB 84.3 . . ? H7WA O7W H7WB 98.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O8 Cu2 O4 C25 174(3) 1_465 . . . ? N9 Cu2 O4 C25 84.6(3) . . . . ? N7 Cu2 O4 C25 -87.0(3) . . . . ? O1W Cu2 O4 C25 177.8(3) . . . . ? O9 Cu1 O7 C26 174.6(13) . . . . ? N4 Cu1 O7 C26 88.3(3) 1_564 . . . ? N1 Cu1 O7 C26 -90.7(3) . . . . ? O7 Cu1 O9 C33 -3.9(15) . . . . ? N4 Cu1 O9 C33 82.2(3) 1_564 . . . ? N1 Cu1 O9 C33 -98.6(3) . . . . ? O9 Cu1 N1 C2 95.0(4) . . . . ? O7 Cu1 N1 C2 -79.0(4) . . . . ? N4 Cu1 N1 C2 -99(3) 1_564 . . . ? O9 Cu1 N1 C1 -87.3(3) . . . . ? O7 Cu1 N1 C1 98.7(4) . . . . ? N4 Cu1 N1 C1 78(3) 1_564 . . . ? O8 Cu2 N7 C44 -79.7(4) 1_465 . . . ? O4 Cu2 N7 C44 103.3(4) . . . . ? N9 Cu2 N7 C44 12.8(13) . . . . ? O1W Cu2 N7 C44 -165.2(4) . . . . ? O8 Cu2 N7 C48 92.7(4) 1_465 . . . ? O4 Cu2 N7 C48 -84.3(4) . . . . ? N9 Cu2 N7 C48 -174.8(10) . . . . ? O1W Cu2 N7 C48 7.2(4) . . . . ? O8 Cu2 N9 C35 51.2(4) 1_465 . . . ? O4 Cu2 N9 C35 -131.8(4) . . . . ? N7 Cu2 N9 C35 -41.1(13) . . . . ? O1W Cu2 N9 C35 136.8(4) . . . . ? O8 Cu2 N9 C39 -127.8(4) 1_465 . . . ? O4 Cu2 N9 C39 49.1(4) . . . . ? N7 Cu2 N9 C39 139.8(10) . . . . ? O1W Cu2 N9 C39 -42.2(4) . . . . ? C2 N1 C1 C5 -0.6(7) . . . . ? Cu1 N1 C1 C5 -178.4(4) . . . . ? C1 N1 C2 C3 1.3(8) . . . . ? Cu1 N1 C2 C3 178.9(4) . . . . ? N1 C2 C3 C4 0.1(9) . . . . ? C2 C3 C4 C5 -2.1(9) . . . . ? N1 C1 C5 C4 -1.3(8) . . . . ? N1 C1 C5 N2 179.6(4) . . . . ? C3 C4 C5 C1 2.6(8) . . . . ? C3 C4 C5 N2 -178.2(5) . . . . ? C6 N2 C5 C1 -13.5(8) . . . . ? C6 N2 C5 C4 167.4(5) . . . . ? C5 N2 C6 O1 2.9(10) . . . . ? C5 N2 C6 C7 -174.5(5) . . . . ? O1 C6 C7 C8 14.0(9) . . . . ? N2 C6 C7 C8 -168.5(5) . . . . ? C6 C7 C8 C9 169.3(5) . . . . ? C7 C8 C9 C10 -166.8(5) . . . . ? C8 C9 C10 C11 170.6(5) . . . . ? C9 C10 C11 C12 -175.6(5) . . . . ? C10 C11 C12 C13 175.9(5) . . . . ? C14 N3 C13 O2 -2.9(9) . . . . ? C14 N3 C13 C12 173.6(5) . . . . ? C11 C12 C13 O2 -15.8(8) . . . . ? C11 C12 C13 N3 167.7(5) . . . . ? C13 N3 C14 C18 -163.1(5) . . . . ? C13 N3 C14 C15 17.3(8) . . . . ? C16 N4 C15 C14 -0.6(7) . . . . ? Cu1 N4 C15 C14 -178.0(4) 1_546 . . . ? C18 C14 C15 N4 0.4(7) . . . . ? N3 C14 C15 N4 -180.0(4) . . . . ? C15 N4 C16 C17 -0.3(8) . . . . ? Cu1 N4 C16 C17 176.9(4) 1_546 . . . ? N4 C16 C17 C18 1.3(9) . . . . ? C15 C14 C18 C17 0.7(8) . . . . ? N3 C14 C18 C17 -179.0(5) . . . . ? C16 C17 C18 C14 -1.5(9) . . . . ? C24 C19 C20 C21 -0.2(7) . . . . ? C24 C19 C20 C26 -179.0(5) . . . . ? C19 C20 C21 C22 -0.6(8) . . . . ? C26 C20 C21 C22 178.3(5) . . . . ? C20 C21 C22 C23 1.0(8) . . . . ? C20 C21 C22 N5 -178.6(5) . . . . ? N5 C22 C23 C24 178.8(5) . . . . ? C21 C22 C23 C24 -0.8(8) . . . . ? C22 C23 C24 C19 0.1(8) . . . . ? C22 C23 C24 C25 -177.6(5) . . . . ? C20 C19 C24 C23 0.4(7) . . . . ? C20 C19 C24 C25 178.2(5) . . . . ? Cu2 O4 C25 O5 3.7(6) . . . . ? Cu2 O4 C25 C24 -175.1(3) . . . . ? C23 C24 C25 O5 -174.6(5) . . . . ? C19 C24 C25 O5 7.7(8) . . . . ? C23 C24 C25 O4 4.2(7) . . . . ? C19 C24 C25 O4 -173.4(4) . . . . ? Cu1 O7 C26 O3 0.7(5) . . . . ? Cu1 O7 C26 C20 -179.0(4) . . . . ? C19 C20 C26 O3 -167.2(5) . . . . ? C21 C20 C26 O3 14.0(7) . . . . ? C19 C20 C26 O7 12.5(7) . . . . ? C21 C20 C26 O7 -166.3(4) . . . . ? C32 C27 C28 C29 1.1(7) . . . . ? C33 C27 C28 C29 -179.0(4) . . . . ? C27 C28 C29 C30 -0.6(7) . . . . ? C27 C28 C29 N6 177.1(4) . . . . ? C28 C29 C30 C31 -0.3(7) . . . . ? N6 C29 C30 C31 -178.0(4) . . . . ? C29 C30 C31 C32 0.8(7) . . . . ? C29 C30 C31 C34 179.9(4) . . . . ? C28 C27 C32 C31 -0.6(7) . . . . ? C33 C27 C32 C31 179.5(4) . . . . ? C30 C31 C32 C27 -0.3(7) . . . . ? C34 C31 C32 C27 -179.5(4) . . . . ? Cu1 O9 C33 O6 2.1(5) . . . . ? Cu1 O9 C33 C27 -179.2(3) . . . . ? C32 C27 C33 O6 176.6(5) . . . . ? C28 C27 C33 O6 -3.4(7) . . . . ? C32 C27 C33 O9 -2.1(7) . . . . ? C28 C27 C33 O9 178.0(4) . . . . ? Cu2 O8 C34 O11 10.4(8) 1_645 . . . ? Cu2 O8 C34 C31 -170.0(3) 1_645 . . . ? C30 C31 C34 O11 1.7(7) . . . . ? C32 C31 C34 O11 -179.2(5) . . . . ? C30 C31 C34 O8 -177.9(4) . . . . ? C32 C31 C34 O8 1.2(7) . . . . ? C39 N9 C35 C36 0.7(7) . . . . ? Cu2 N9 C35 C36 -178.3(4) . . . . ? N9 C35 C36 C37 -0.3(8) . . . . ? C35 C36 C37 C38 0.4(9) . . . . ? C36 C37 C38 C39 -0.9(8) . . . . ? C36 C37 C38 N10 179.9(5) . . . . ? C40 N10 C38 C37 -179.4(12) . . . . ? C40' N10 C38 C37 -146.7(19) . . . . ? C40 N10 C38 C39 1.4(15) . . . . ? C40' N10 C38 C39 34(2) . . . . ? C35 N9 C39 C38 -1.3(8) . . . . ? Cu2 N9 C39 C38 177.8(4) . . . . ? C37 C38 C39 N9 1.4(8) . . . . ? N10 C38 C39 N9 -179.4(5) . . . . ? C38 N10 C40 O10 23(3) . . . . ? C40' N10 C40 O10 -62(4) . . . . ? C38 N10 C40 C41 -172.0(10) . . . . ? C40' N10 C40 C41 103(5) . . . . ? O10 C40 C41 C42 15(3) . . . . ? N10 C40 C41 C42 -150.2(16) . . . . ? C40 C41 C42 C43 59(2) . . . . ? O10B O10A C40' N10 -84(3) . . . . ? O10B O10A C40' C41' 106(4) . . . . ? C40 N10 C40' O10A 116(6) . . . . ? C38 N10 C40' O10A 1(4) . . . . ? C40 N10 C40' C41' -72(4) . . . . ? C38 N10 C40' C41' 173.3(18) . . . . ? C40 N10 C40' O10B 39(3) . . . . ? C38 N10 C40' O10B -76(2) . . . . ? O10A O10B C40' N10 122(3) . . . . ? O10A O10B C40' C41' -128(4) . . . . ? O10A C40' C41' C42' -23(5) . . . . ? N10 C40' C41' C42' 166(3) . . . . ? O10B C40' C41' C42' 68(3) . . . . ? O10A C40' C41' C43 5(5) . . . . ? N10 C40' C41' C43 -166(2) . . . . ? O10B C40' C41' C43 96(3) . . . . ? C40' C41' C42' C43 117(4) . . . . ? C41' C42' C43 C42 75(3) . . . . ? C41' C42' C43 C43 142(2) . . . 2_656 ? C41 C42 C43 C42' -72(4) . . . . ? C41 C42 C43 C41' 0.6(19) . . . . ? C41 C42 C43 C43 167.0(13) . . . 2_656 ? C40' C41' C43 C42' -72(4) . . . . ? C42' C41' C43 C42 -49(3) . . . . ? C40' C41' C43 C42 -121(3) . . . . ? C42' C41' C43 C43 -73(4) . . . 2_656 ? C40' C41' C43 C43 -145(2) . . . 2_656 ? C48 N7 C44 C45 -3.9(8) . . . . ? Cu2 N7 C44 C45 169.0(4) . . . . ? N7 C44 C45 C66 1.9(8) . . . . ? N7 C44 C45 N8 -177.2(5) . . . . ? C49 N8 C45 C66 0.4(9) . . . . ? C49 N8 C45 C44 179.4(5) . . . . ? C44 N7 C48 C68 3.0(8) . . . . ? Cu2 N7 C48 C68 -169.4(5) . . . . ? C45 N8 C49 O12 -1.9(10) . . . . ? C45 N8 C49 C50 179.2(5) . . . . ? O12 C49 C50 C51 -75.4(8) . . . . ? N8 C49 C50 C51 103.5(6) . . . . ? C49 C50 C51 C52 -176.2(5) . . . . ? C50 C51 C52 C52 -178.9(6) . . . 2_965 ? C44 C45 C66 C68 0.9(9) . . . . ? N8 C45 C66 C68 179.9(6) . . . . ? N7 C48 C68 C66 -0.3(10) . . . . ? C45 C66 C68 C48 -1.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.290 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.079 ###########END _database_code_depnum_ccdc_archive 'CCDC 901804'