# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_do2nph _database_code_depnum_ccdc_archive 'CCDC 904673' #TrackingRef 'web_deposit_cif_file_0_RitaDelgado_1353939840.revision for CCDC 904673 - 904676.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Cl2 N6 O16' _chemical_formula_weight 711.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6397(3) _cell_length_b 9.7922(4) _cell_length_c 18.6551(9) _cell_angle_alpha 100.664(3) _cell_angle_beta 99.990(3) _cell_angle_gamma 100.033(2) _cell_volume 1492.37(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 485 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 30.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9197 _exptl_absorpt_correction_T_max 0.9939 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 23591 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 30.53 _reflns_number_total 8974 _reflns_number_gt 6963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Platon (Speck, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. O-H phenol groups were refined with restraints on O-H distances of 0.90 A. A water molecule was also refined with O-H and H..H distances restrained to 0.83 and 1.33 A respectively. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.3497P] 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 8974 _refine_ls_number_parameters 480 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl10 Cl 0.84513(5) 0.12219(5) 0.43021(2) 0.02715(12) Uani 1 d . . . O101 O 0.8782(2) -0.0069(2) 0.39357(11) 0.0510(4) Uani 1 d . . . O102 O 0.69152(19) 0.13649(16) 0.39072(10) 0.0440(4) Uani 1 d . . . O103 O 0.8311(3) 0.1147(2) 0.50476(9) 0.0539(5) Uani 1 d . . . O104 O 0.9656(2) 0.2420(2) 0.43131(13) 0.0649(6) Uani 1 d . . . O201 O 0.1704(2) 0.5460(3) 0.05812(10) 0.0618(6) Uani 0.462(4) d P A 1 O202 O 0.3838(2) 0.4343(2) 0.07377(16) 0.0740(7) Uani 0.462(4) d P A 1 O203 O 0.2689(4) 0.5586(4) 0.17988(18) 0.0436(10) Uani 0.462(4) d P A 1 O204 O 0.4501(5) 0.6857(5) 0.1251(3) 0.0609(13) Uani 0.462(4) d P A 1 Cl20 Cl 0.32036(12) 0.56531(11) 0.11078(12) 0.0270(4) Uani 0.462(4) d P A 1 O205 O 0.1704(2) 0.5460(3) 0.05812(10) 0.0618(6) Uani 0.538(4) d P A 2 O206 O 0.3838(2) 0.4343(2) 0.07377(16) 0.0740(7) Uani 0.538(4) d P A 2 O207 O 0.3907(4) 0.6507(3) 0.02925(19) 0.0448(8) Uani 0.538(4) d P A 2 O208 O 0.3974(5) 0.6289(4) 0.15215(17) 0.0470(9) Uani 0.538(4) d P A 2 Cl21 Cl 0.33304(12) 0.56007(10) 0.07493(10) 0.0272(3) Uani 0.538(4) d P A 2 N1 N 0.84073(18) 0.49849(15) 0.31859(8) 0.0222(3) Uani 1 d . . . C2 C 0.8550(2) 0.37556(18) 0.26342(11) 0.0284(4) Uani 1 d . . . H2A H 0.8513 0.2917 0.2862 0.034 Uiso 1 calc R . . H2B H 0.9601 0.3960 0.2489 0.034 Uiso 1 calc R . . C3 C 0.7207(2) 0.3420(2) 0.19436(11) 0.0316(4) Uani 1 d . . . H3A H 0.7424 0.2690 0.1552 0.038 Uiso 1 calc R . . H3B H 0.6175 0.3032 0.2068 0.038 Uiso 1 calc R . . N4 N 0.7081(2) 0.47326(19) 0.16554(9) 0.0306(4) Uani 1 d . . . H4A H 0.612(3) 0.461(3) 0.1329(15) 0.038(6) Uiso 1 d . . . H4B H 0.709(4) 0.540(3) 0.2012(17) 0.052(8) Uiso 1 d . . . C5 C 0.8380(3) 0.5174(3) 0.12560(12) 0.0440(6) Uani 1 d . . . H5A H 0.8206 0.4498 0.0769 0.053 Uiso 1 calc R . . H5B H 0.9440 0.5160 0.1556 0.053 Uiso 1 calc R . . C6 C 0.8364(3) 0.6654(3) 0.11328(12) 0.0442(6) Uani 1 d . . . H6A H 0.9121 0.6892 0.0810 0.053 Uiso 1 calc R . . H6B H 0.7273 0.6685 0.0874 0.053 Uiso 1 calc R . . N7 N 0.8829(2) 0.7710(2) 0.18484(10) 0.0374(4) Uani 1 d . . . C8 C 1.0588(3) 0.8109(3) 0.21118(13) 0.0431(6) Uani 1 d . . . H8A H 1.1044 0.8791 0.1833 0.052 Uiso 1 calc R . . H8B H 1.1045 0.7252 0.2009 0.052 Uiso 1 calc R . . C9 C 1.1064(3) 0.8774(2) 0.29367(13) 0.0352(4) Uani 1 d . . . H9A H 1.2248 0.8953 0.3102 0.042 Uiso 1 calc R . . H9B H 1.0733 0.9698 0.3033 0.042 Uiso 1 calc R . . N10 N 1.0285(2) 0.78137(16) 0.33702(9) 0.0235(3) Uani 1 d . . . H1A H 1.025(3) 0.831(3) 0.3780(16) 0.040(7) Uiso 1 d . . . H1B H 0.935(3) 0.753(3) 0.3154(15) 0.034(6) Uiso 1 d . . . C11 C 1.1050(2) 0.65973(19) 0.34777(10) 0.0255(3) Uani 1 d . . . H11A H 1.2080 0.6941 0.3849 0.031 Uiso 1 calc R . . H11B H 1.1278 0.6133 0.3000 0.031 Uiso 1 calc R . . C12 C 0.9918(2) 0.55418(19) 0.37485(10) 0.0262(3) Uani 1 d . . . H12A H 1.0433 0.4747 0.3843 0.031 Uiso 1 calc R . . H12B H 0.9685 0.6013 0.4223 0.031 Uiso 1 calc R . . C13 C 0.7021(2) 0.45908(18) 0.35279(10) 0.0261(3) Uani 1 d . . . H13A H 0.7241 0.3874 0.3821 0.031 Uiso 1 calc R . . H13B H 0.6059 0.4145 0.3126 0.031 Uiso 1 calc R . . C14 C 0.6661(2) 0.58300(18) 0.40279(9) 0.0230(3) Uani 1 d . . . C15 C 0.6801(2) 0.5876(2) 0.47820(10) 0.0262(3) Uani 1 d . . . H15 H 0.7180 0.5147 0.4988 0.031 Uiso 1 calc R . . C16 C 0.6391(2) 0.6982(2) 0.52393(10) 0.0275(4) Uani 1 d . . . C17 C 0.5789(2) 0.8042(2) 0.49591(11) 0.0298(4) Uani 1 d . . . H17 H 0.5495 0.8782 0.5279 0.036 Uiso 1 calc R . . C18 C 0.5625(2) 0.8001(2) 0.42060(10) 0.0277(4) Uani 1 d . . . H18 H 0.5197 0.8710 0.4002 0.033 Uiso 1 calc R . . C19 C 0.6085(2) 0.69207(18) 0.37409(9) 0.0231(3) Uani 1 d . . . N20 N 0.65922(19) 0.7018(2) 0.60292(9) 0.0354(4) Uani 1 d . . . O21 O 0.6922(2) 0.5951(2) 0.62462(8) 0.0438(4) Uani 1 d . . . O22 O 0.6422(2) 0.8070(2) 0.64506(9) 0.0527(5) Uani 1 d . . . O23 O 0.59822(18) 0.68565(15) 0.30021(7) 0.0304(3) Uani 1 d D . . H23 H 0.561(3) 0.7599(19) 0.2884(14) 0.036 Uiso 1 d D . . C24 C 0.8067(3) 0.8948(3) 0.18131(13) 0.0398(5) Uani 1 d . . . H24A H 0.8432 0.9625 0.2304 0.048 Uiso 1 calc R . . H24B H 0.6889 0.8610 0.1737 0.048 Uiso 1 calc R . . C25 C 0.8387(2) 0.9754(2) 0.12147(11) 0.0302(4) Uani 1 d . . . C26 C 0.7333(2) 0.9400(2) 0.05289(12) 0.0300(4) Uani 1 d . . . H26 H 0.6443 0.8619 0.0423 0.036 Uiso 1 calc R . . C27 C 0.7569(2) 1.0186(2) -0.00087(10) 0.0263(3) Uani 1 d . . . C28 C 0.8834(2) 1.1335(2) 0.01214(10) 0.0269(4) Uani 1 d . . . H28 H 0.8965 1.1868 -0.0249 0.032 Uiso 1 calc R . . C29 C 0.9906(2) 1.1696(2) 0.08003(10) 0.0286(4) Uani 1 d . . . H29 H 1.0795 1.2477 0.0899 0.034 Uiso 1 calc R . . C30 C 0.9687(2) 1.0913(2) 0.13459(10) 0.0299(4) Uani 1 d . . . N31 N 0.6432(2) 0.9795(2) -0.07240(10) 0.0356(4) Uani 1 d . . . O32 O 0.5264(2) 0.8841(2) -0.08171(11) 0.0535(5) Uani 1 d . . . O33 O 0.6700(2) 1.0465(2) -0.12061(9) 0.0537(5) Uani 1 d . . . O34 O 1.0687(2) 1.1273(2) 0.20250(8) 0.0445(4) Uani 1 d D . . H34 H 1.158(2) 1.189(3) 0.2048(17) 0.053 Uiso 1 d D . . O100 O 0.48975(17) 0.91563(16) 0.26883(7) 0.0308(3) Uani 1 d D . . H101 H 0.456(3) 0.937(2) 0.2262(10) 0.037 Uiso 1 d D . . H102 H 0.550(3) 0.994(2) 0.2931(12) 0.037 Uiso 1 d D . . O200 O 1.3241(4) 1.3053(5) 0.22122(19) 0.0551(10) Uani 0.50 d P . . O300 O 0.7323(6) 0.5920(4) 0.77508(18) 0.0601(11) Uani 0.50 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl10 0.0263(2) 0.0257(2) 0.0280(2) 0.00771(15) 0.00037(16) 0.00524(16) O101 0.0479(10) 0.0501(10) 0.0577(11) -0.0011(8) 0.0168(8) 0.0263(8) O102 0.0327(8) 0.0343(8) 0.0594(10) 0.0158(7) -0.0096(7) 0.0063(6) O103 0.0698(12) 0.0609(11) 0.0244(7) 0.0018(7) 0.0055(8) 0.0090(9) O104 0.0398(10) 0.0584(12) 0.0852(15) 0.0371(11) -0.0116(9) -0.0172(9) O201 0.0402(10) 0.1146(18) 0.0343(8) 0.0096(10) 0.0020(7) 0.0392(11) O202 0.0388(10) 0.0399(10) 0.131(2) 0.0134(11) -0.0155(11) 0.0138(8) O203 0.044(2) 0.068(2) 0.0274(16) 0.0090(15) 0.0129(14) 0.0302(18) O204 0.048(2) 0.042(2) 0.085(3) 0.003(2) 0.023(2) -0.0107(18) Cl20 0.0219(5) 0.0318(5) 0.0265(9) 0.0003(4) 0.0060(5) 0.0091(4) O205 0.0402(10) 0.1146(18) 0.0343(8) 0.0096(10) 0.0020(7) 0.0392(11) O206 0.0388(10) 0.0399(10) 0.131(2) 0.0134(11) -0.0155(11) 0.0138(8) O207 0.0356(16) 0.0504(18) 0.0539(18) 0.0284(15) 0.0129(14) 0.0020(13) O208 0.054(2) 0.0408(18) 0.0291(14) -0.0005(13) -0.0190(15) 0.0014(16) Cl21 0.0230(4) 0.0304(4) 0.0269(7) 0.0101(4) -0.0012(4) 0.0045(3) N1 0.0226(7) 0.0183(6) 0.0231(6) 0.0038(5) -0.0009(5) 0.0040(5) C2 0.0317(9) 0.0198(8) 0.0332(9) 0.0043(6) 0.0022(7) 0.0107(7) C3 0.0321(10) 0.0235(8) 0.0334(9) -0.0044(7) -0.0001(8) 0.0094(7) N4 0.0332(9) 0.0361(9) 0.0227(7) 0.0002(6) 0.0018(6) 0.0190(7) C5 0.0589(14) 0.0639(15) 0.0302(10) 0.0212(10) 0.0247(10) 0.0421(13) C6 0.0564(14) 0.0643(15) 0.0341(10) 0.0274(10) 0.0260(10) 0.0379(12) N7 0.0426(10) 0.0538(11) 0.0370(9) 0.0264(8) 0.0264(8) 0.0311(9) C8 0.0438(12) 0.0647(15) 0.0479(12) 0.0362(11) 0.0334(10) 0.0346(12) C9 0.0334(10) 0.0345(10) 0.0502(12) 0.0220(9) 0.0244(9) 0.0115(8) N10 0.0237(7) 0.0222(7) 0.0263(7) 0.0055(6) 0.0091(6) 0.0058(6) C11 0.0236(8) 0.0250(8) 0.0280(8) 0.0055(6) 0.0034(6) 0.0084(7) C12 0.0251(8) 0.0248(8) 0.0271(8) 0.0088(6) -0.0015(7) 0.0045(7) C13 0.0266(8) 0.0206(8) 0.0288(8) 0.0071(6) 0.0021(7) 0.0007(6) C14 0.0195(7) 0.0223(7) 0.0246(7) 0.0073(6) 0.0016(6) -0.0014(6) C15 0.0201(8) 0.0317(9) 0.0251(8) 0.0108(7) 0.0021(6) -0.0012(7) C16 0.0179(8) 0.0409(10) 0.0206(7) 0.0068(7) 0.0043(6) -0.0021(7) C17 0.0254(9) 0.0351(10) 0.0277(8) 0.0032(7) 0.0089(7) 0.0043(7) C18 0.0264(9) 0.0291(9) 0.0287(8) 0.0069(7) 0.0074(7) 0.0065(7) C19 0.0221(8) 0.0245(8) 0.0215(7) 0.0065(6) 0.0032(6) 0.0014(6) N20 0.0194(7) 0.0605(12) 0.0229(7) 0.0085(7) 0.0040(6) 0.0008(7) O21 0.0378(8) 0.0665(11) 0.0275(7) 0.0215(7) 0.0050(6) 0.0024(8) O22 0.0434(10) 0.0853(14) 0.0251(7) -0.0023(8) 0.0052(7) 0.0196(9) O23 0.0428(8) 0.0315(7) 0.0215(6) 0.0092(5) 0.0060(5) 0.0175(6) C24 0.0430(12) 0.0558(13) 0.0440(11) 0.0294(10) 0.0299(10) 0.0326(11) C25 0.0300(9) 0.0408(10) 0.0335(9) 0.0181(8) 0.0189(8) 0.0209(8) C26 0.0245(9) 0.0309(9) 0.0420(10) 0.0129(8) 0.0150(8) 0.0123(7) C27 0.0241(8) 0.0314(9) 0.0265(8) 0.0057(7) 0.0072(7) 0.0132(7) C28 0.0288(9) 0.0311(9) 0.0270(8) 0.0098(7) 0.0124(7) 0.0128(7) C29 0.0266(9) 0.0323(9) 0.0290(8) 0.0059(7) 0.0100(7) 0.0088(7) C30 0.0280(9) 0.0427(11) 0.0240(8) 0.0075(7) 0.0094(7) 0.0167(8) N31 0.0279(8) 0.0451(10) 0.0322(8) -0.0005(7) 0.0046(7) 0.0150(8) O32 0.0355(9) 0.0522(10) 0.0580(11) -0.0063(8) -0.0009(8) 0.0007(8) O33 0.0488(10) 0.0846(14) 0.0291(8) 0.0171(8) 0.0041(7) 0.0170(10) O34 0.0432(9) 0.0664(11) 0.0253(7) 0.0084(7) 0.0044(6) 0.0201(8) O100 0.0317(7) 0.0390(8) 0.0235(6) 0.0080(5) 0.0034(5) 0.0139(6) O200 0.0341(17) 0.092(3) 0.0331(16) 0.0268(19) -0.0019(13) -0.0078(18) O300 0.087(3) 0.051(2) 0.0236(14) 0.0110(14) -0.0045(16) -0.024(2) _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 Cl10 O104 1.4209(18) . ? Cl10 O101 1.4213(16) . ? Cl10 O103 1.4308(17) . ? Cl10 O102 1.4448(15) . ? O201 Cl20 1.443(2) . ? O202 Cl20 1.572(2) . ? O203 Cl20 1.443(4) . ? O204 Cl20 1.427(4) . ? O205 Cl21 1.362(2) . ? O206 Cl21 1.375(2) . ? O207 Cl21 1.426(3) . ? O208 Cl21 1.439(3) . ? N1 C2 1.470(2) . ? N1 C12 1.472(2) . ? N1 C13 1.478(2) . ? C2 C3 1.519(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.496(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.498(3) . ? N4 H4A 0.92(3) . ? N4 H4B 0.84(3) . ? C5 C6 1.511(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N7 1.474(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 C8 1.472(3) . ? N7 C24 1.483(2) . ? C8 C9 1.509(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N10 1.497(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N10 C11 1.488(2) . ? N10 H1A 0.84(3) . ? N10 H1B 0.81(3) . ? C11 C12 1.514(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.501(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.383(2) . ? C14 C19 1.407(2) . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 C17 1.384(3) . ? C16 N20 1.447(2) . ? C17 C18 1.380(3) . ? C17 H17 0.9500 . ? C18 C19 1.398(3) . ? C18 H18 0.9500 . ? C19 O23 1.355(2) . ? N20 O22 1.223(3) . ? N20 O21 1.247(2) . ? O23 H23 0.893(10) . ? C24 C25 1.518(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.381(3) . ? C25 C30 1.403(3) . ? C26 C27 1.393(3) . ? C26 H26 0.9500 . ? C27 C28 1.378(3) . ? C27 N31 1.455(2) . ? C28 C29 1.378(3) . ? C28 H28 0.9500 . ? C29 C30 1.402(3) . ? C29 H29 0.9500 . ? C30 O34 1.351(2) . ? N31 O32 1.212(3) . ? N31 O33 1.237(3) . ? O34 H34 0.879(10) . ? O100 H101 0.875(15) . ? O100 H102 0.850(16) . ? O200 O300 1.187(6) 2_776 ? O300 O200 1.187(6) 2_776 ? 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 O104 Cl10 O101 111.92(13) . . ? O104 Cl10 O103 110.09(13) . . ? O101 Cl10 O103 109.62(12) . . ? O104 Cl10 O102 109.60(10) . . ? O101 Cl10 O102 107.78(11) . . ? O103 Cl10 O102 107.71(12) . . ? O204 Cl20 O201 124.3(3) . . ? O204 Cl20 O203 108.0(3) . . ? O201 Cl20 O203 102.77(18) . . ? O204 Cl20 O202 106.1(2) . . ? O201 Cl20 O202 99.64(14) . . ? O203 Cl20 O202 116.7(2) . . ? O205 Cl21 O206 114.76(15) . . ? O205 Cl21 O207 104.18(17) . . ? O206 Cl21 O207 118.7(2) . . ? O205 Cl21 O208 110.6(2) . . ? O206 Cl21 O208 99.49(18) . . ? O207 Cl21 O208 109.0(2) . . ? C2 N1 C12 110.71(14) . . ? C2 N1 C13 109.96(14) . . ? C12 N1 C13 112.08(14) . . ? N1 C2 C3 111.34(14) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N4 C3 C2 110.38(15) . . ? N4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? N4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C3 N4 C5 113.75(15) . . ? C3 N4 H4A 111.1(16) . . ? C5 N4 H4A 107.0(16) . . ? C3 N4 H4B 109(2) . . ? C5 N4 H4B 110(2) . . ? H4A N4 H4B 106(3) . . ? N4 C5 C6 109.64(17) . . ? N4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? N4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? N7 C6 C5 110.87(17) . . ? N7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 N7 C6 111.44(17) . . ? C8 N7 C24 113.4(2) . . ? C6 N7 C24 111.62(17) . . ? N7 C8 C9 111.78(16) . . ? N7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N10 C9 C8 110.52(18) . . ? N10 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N10 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 N10 C9 115.23(14) . . ? C11 N10 H1A 111.3(18) . . ? C9 N10 H1A 107.8(18) . . ? C11 N10 H1B 110.4(18) . . ? C9 N10 H1B 107.0(18) . . ? H1A N10 H1B 105(2) . . ? N10 C11 C12 108.84(14) . . ? N10 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N10 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N1 C12 C11 110.17(14) . . ? N1 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N1 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N1 C13 C14 113.45(14) . . ? N1 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? N1 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C19 118.38(16) . . ? C15 C14 C13 120.04(15) . . ? C19 C14 C13 121.46(15) . . ? C14 C15 C16 120.22(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 121.78(16) . . ? C17 C16 N20 119.44(18) . . ? C15 C16 N20 118.77(17) . . ? C18 C17 C16 118.62(17) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 120.39(17) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? O23 C19 C18 122.47(15) . . ? O23 C19 C14 116.98(15) . . ? C18 C19 C14 120.55(15) . . ? O22 N20 O21 123.04(17) . . ? O22 N20 C16 119.31(19) . . ? O21 N20 C16 117.64(18) . . ? C19 O23 H23 109.1(16) . . ? N7 C24 C25 116.84(15) . . ? N7 C24 H24A 108.1 . . ? C25 C24 H24A 108.1 . . ? N7 C24 H24B 108.1 . . ? C25 C24 H24B 108.1 . . ? H24A C24 H24B 107.3 . . ? C26 C25 C30 117.98(17) . . ? C26 C25 C24 119.9(2) . . ? C30 C25 C24 122.02(19) . . ? C25 C26 C27 120.26(19) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 121.91(17) . . ? C28 C27 N31 119.07(17) . . ? C26 C27 N31 119.01(18) . . ? C27 C28 C29 118.63(17) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? C28 C29 C30 120.11(19) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? O34 C30 C29 121.3(2) . . ? O34 C30 C25 117.52(18) . . ? C29 C30 C25 121.10(17) . . ? O32 N31 O33 123.20(19) . . ? O32 N31 C27 118.71(19) . . ? O33 N31 C27 118.08(19) . . ? C30 O34 H34 114(2) . . ? H101 O100 H102 100.7(18) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.594 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.110 data_cb_do2nph _database_code_depnum_ccdc_archive 'CCDC 904674' #TrackingRef 'web_deposit_cif_file_0_RitaDelgado_1353939840.revision for CCDC 904673 - 904676.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H35 N6 O7.50' _chemical_formula_weight 527.58 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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P-42(1)c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 16.7755(5) _cell_length_b 16.7755(5) _cell_length_c 17.8638(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5027.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 547 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 29.90 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9896 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 64273 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 29.14 _reflns_number_total 6773 _reflns_number_gt 5881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Platon (Spek, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1033P)^2^+2.2512P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0(3) _refine_ls_number_reflns 6773 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.79543(11) 0.30080(13) 0.18208(12) 0.0320(4) Uani 1 d . . . C2 C 0.77212(15) 0.38316(15) 0.19573(16) 0.0388(6) Uani 1 d . . . H2A H 0.7278 0.3980 0.1619 0.047 Uiso 1 calc R . . H2B H 0.8177 0.4191 0.1854 0.047 Uiso 1 calc R . . C3 C 0.7457(2) 0.39233(16) 0.27753(17) 0.0462(7) Uani 1 d . . . H3A H 0.7919 0.3849 0.3113 0.055 Uiso 1 calc R . . H3B H 0.7238 0.4464 0.2859 0.055 Uiso 1 calc R . . N4 N 0.68392(19) 0.33141(13) 0.29345(13) 0.0464(6) Uani 1 d . . . H4 H 0.691(3) 0.291(3) 0.262(2) 0.070(12) Uiso 1 d . . . C5 C 0.60465(19) 0.34928(17) 0.2607(2) 0.0591(10) Uani 1 d . . . H5A H 0.6094 0.3921 0.2228 0.071 Uiso 1 calc R . . H5B H 0.5675 0.3674 0.3002 0.071 Uiso 1 calc R . . C6 C 0.57283(15) 0.27222(17) 0.22383(19) 0.0438(6) Uani 1 d . . . H6A H 0.5442 0.2394 0.2613 0.053 Uiso 1 calc R . . H6B H 0.5354 0.2855 0.1829 0.053 Uiso 1 calc R . . N7 N 0.64111(11) 0.22847(11) 0.19438(11) 0.0281(4) Uani 1 d . . . C8 C 0.64503(14) 0.14332(13) 0.21031(12) 0.0288(4) Uani 1 d . . . H8A H 0.6906 0.1196 0.1830 0.035 Uiso 1 calc R . . H8B H 0.5956 0.1172 0.1925 0.035 Uiso 1 calc R . . C9 C 0.65493(14) 0.12814(15) 0.29456(13) 0.0333(5) Uani 1 d . . . H9A H 0.6055 0.1442 0.3208 0.040 Uiso 1 calc R . . H9B H 0.6631 0.0704 0.3032 0.040 Uiso 1 calc R . . N10 N 0.72221(13) 0.17217(12) 0.32570(12) 0.0345(4) Uani 1 d . . . C11 C 0.7212(4) 0.2304(3) 0.3847(3) 0.0278(10) Uani 0.630(11) d P A 1 H11A H 0.7758 0.2518 0.3914 0.033 Uiso 0.630(11) calc PR A 1 H11B H 0.7055 0.2040 0.4320 0.033 Uiso 0.630(11) calc PR A 1 C12 C 0.6637(3) 0.3000(2) 0.3692(2) 0.0314(12) Uani 0.630(11) d P A 1 H12A H 0.6078 0.2811 0.3704 0.038 Uiso 0.630(11) calc PR A 1 H12B H 0.6703 0.3422 0.4074 0.038 Uiso 0.630(11) calc PR A 1 C11A C 0.6849(8) 0.2209(5) 0.3901(5) 0.0336(19) Uani 0.370(11) d P A 2 H11C H 0.6260 0.2182 0.3883 0.040 Uiso 0.370(11) calc PR A 2 H11D H 0.7032 0.2008 0.4393 0.040 Uiso 0.370(11) calc PR A 2 C12A C 0.7135(5) 0.3049(4) 0.3773(4) 0.033(2) Uani 0.370(11) d P A 2 H12C H 0.7723 0.3074 0.3808 0.040 Uiso 0.370(11) calc PR A 2 H12D H 0.6906 0.3411 0.4155 0.040 Uiso 0.370(11) calc PR A 2 C13 C 0.76014(13) 0.26137(16) 0.11767(14) 0.0339(5) Uani 1 d . . . H13A H 0.7827 0.2070 0.1136 0.041 Uiso 1 calc R . . H13B H 0.7752 0.2910 0.0719 0.041 Uiso 1 calc R . . C14 C 0.66913(13) 0.25521(15) 0.12126(13) 0.0306(5) Uani 1 d . . . H14A H 0.6456 0.3080 0.1101 0.037 Uiso 1 calc R . . H14B H 0.6505 0.2174 0.0825 0.037 Uiso 1 calc R . . C15 C 0.88124(13) 0.28472(19) 0.19025(15) 0.0406(6) Uani 1 d . . . H15A H 0.8881 0.2277 0.2031 0.049 Uiso 1 calc R . . H15B H 0.9015 0.3164 0.2330 0.049 Uiso 1 calc R . . C16 C 0.93267(14) 0.3030(2) 0.12213(15) 0.0418(6) Uani 1 d . . . C17 C 0.94692(14) 0.24311(18) 0.07103(16) 0.0418(6) Uani 1 d . . . H17 H 0.9247 0.1917 0.0790 0.050 Uiso 1 calc R . . C18 C 0.99363(16) 0.25712(19) 0.00782(16) 0.0452(6) Uani 1 d . . . C19 C 1.02723(17) 0.3325(2) -0.00533(17) 0.0506(8) Uani 1 d . . . H19 H 1.0583 0.3419 -0.0489 0.061 Uiso 1 calc R . . C20 C 1.01443(17) 0.3923(2) 0.04586(17) 0.0526(8) Uani 1 d . . . H20 H 1.0378 0.4432 0.0376 0.063 Uiso 1 calc R . . C21 C 0.96725(14) 0.37994(19) 0.11052(15) 0.0423(6) Uani 1 d . . . N22 N 1.00758(14) 0.19332(19) -0.04497(16) 0.0524(6) Uani 1 d . . . O23 O 0.97049(14) 0.13107(17) -0.03746(18) 0.0670(7) Uani 1 d . . . O24 O 1.05555(17) 0.20282(19) -0.09711(16) 0.0733(8) Uani 1 d . . . O25 O 0.95697(13) 0.43705(16) 0.15957(12) 0.0552(6) Uani 1 d . . . C26 C 0.79733(15) 0.13042(15) 0.32473(17) 0.0400(6) Uani 1 d . . . H26A H 0.8405 0.1700 0.3314 0.048 Uiso 1 calc R . . H26B H 0.8042 0.1063 0.2746 0.048 Uiso 1 calc R . . C27 C 0.80835(15) 0.06533(14) 0.38288(17) 0.0385(6) Uani 1 d . . . C28 C 0.75071(15) 0.04548(13) 0.43471(15) 0.0358(5) Uani 1 d . . . H28 H 0.7015 0.0734 0.4351 0.043 Uiso 1 calc R . . C29 C 0.76412(17) -0.01546(14) 0.48676(16) 0.0403(6) Uani 1 d . . . C30 C 0.83495(18) -0.05833(15) 0.48725(18) 0.0456(7) Uani 1 d . . . H30 H 0.8432 -0.1000 0.5224 0.055 Uiso 1 calc R . . C31 C 0.89319(18) -0.03925(15) 0.43568(19) 0.0466(7) Uani 1 d . . . H31 H 0.9418 -0.0683 0.4355 0.056 Uiso 1 calc R . . C32 C 0.88185(15) 0.02251(14) 0.38321(17) 0.0402(6) Uani 1 d . . . N33 N 0.70375(16) -0.03339(14) 0.54163(16) 0.0492(6) Uani 1 d . . . O34 O 0.64365(14) 0.00847(13) 0.54487(14) 0.0555(6) Uani 1 d . . . O35 O 0.71431(19) -0.08938(16) 0.5857(2) 0.0836(10) Uani 1 d . . . O36 O 0.93770(13) 0.04120(13) 0.33492(16) 0.0565(6) Uani 1 d . . . H36A H 0.9218 0.0789 0.3078 0.068 Uiso 1 calc R . . O100 O 0.9301(3) 0.4527(2) 0.3244(3) 0.134(2) Uani 1 d . . . O200 O 0.9400(4) 0.0841(5) 0.1904(6) 0.114(3) Uani 0.50 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0195(8) 0.0368(10) 0.0396(9) 0.0101(8) -0.0020(7) -0.0043(7) C2 0.0309(11) 0.0310(11) 0.0546(15) 0.0145(11) -0.0095(11) -0.0087(9) C3 0.0624(18) 0.0244(11) 0.0518(15) 0.0017(11) -0.0148(14) -0.0044(11) N4 0.0798(19) 0.0200(9) 0.0394(11) 0.0012(8) 0.0134(12) 0.0011(10) C5 0.0470(16) 0.0298(13) 0.101(3) -0.0045(15) 0.0331(18) 0.0031(11) C6 0.0274(11) 0.0395(13) 0.0644(17) 0.0076(12) 0.0152(12) 0.0020(10) N7 0.0232(8) 0.0286(9) 0.0325(9) 0.0053(7) 0.0036(7) -0.0013(7) C8 0.0311(10) 0.0248(9) 0.0306(10) 0.0010(8) -0.0043(8) -0.0057(8) C9 0.0290(11) 0.0369(12) 0.0339(11) 0.0088(9) -0.0031(9) 0.0013(9) N10 0.0401(11) 0.0266(9) 0.0368(9) -0.0077(8) -0.0136(9) 0.0149(8) C11 0.031(2) 0.0253(18) 0.0272(18) -0.0032(14) -0.0019(19) 0.0008(17) C12 0.032(3) 0.0246(16) 0.0375(19) -0.0014(14) 0.0034(16) 0.0051(15) C11A 0.043(5) 0.028(3) 0.030(3) 0.002(3) 0.006(4) 0.008(4) C12A 0.035(5) 0.032(3) 0.032(3) -0.004(2) 0.000(3) 0.005(3) C13 0.0234(10) 0.0417(12) 0.0365(11) 0.0069(10) 0.0025(9) -0.0058(9) C14 0.0230(9) 0.0394(12) 0.0294(10) 0.0092(9) -0.0032(8) -0.0055(8) C15 0.0190(9) 0.0583(16) 0.0444(13) 0.0234(12) -0.0018(9) -0.0023(10) C16 0.0183(9) 0.0660(17) 0.0412(13) 0.0214(13) -0.0055(9) -0.0063(10) C17 0.0193(10) 0.0532(15) 0.0529(14) 0.0183(13) -0.0013(10) 0.0000(10) C18 0.0233(10) 0.0639(17) 0.0485(14) 0.0165(14) -0.0026(10) -0.0021(11) C19 0.0340(13) 0.077(2) 0.0403(14) 0.0167(14) 0.0024(11) -0.0106(13) C20 0.0365(14) 0.076(2) 0.0457(15) 0.0166(15) 0.0039(12) -0.0262(14) C21 0.0242(10) 0.0665(18) 0.0364(12) 0.0102(12) -0.0037(9) -0.0167(11) N22 0.0309(11) 0.0669(17) 0.0592(15) 0.0091(14) -0.0018(11) 0.0061(11) O23 0.0441(12) 0.0683(16) 0.0885(19) 0.0041(15) 0.0063(13) 0.0006(11) O24 0.0647(16) 0.087(2) 0.0681(15) 0.0035(15) 0.0234(13) 0.0003(15) O25 0.0424(11) 0.0760(15) 0.0473(11) 0.0072(11) 0.0001(9) -0.0366(11) C26 0.0309(11) 0.0303(11) 0.0588(15) 0.0014(11) -0.0150(11) 0.0043(9) C27 0.0345(12) 0.0227(9) 0.0582(15) -0.0077(10) -0.0212(11) 0.0064(9) C28 0.0365(12) 0.0200(9) 0.0508(13) -0.0053(9) -0.0231(11) 0.0064(9) C29 0.0468(14) 0.0238(10) 0.0503(14) -0.0028(10) -0.0263(12) 0.0053(10) C30 0.0494(15) 0.0235(10) 0.0638(17) -0.0052(11) -0.0359(14) 0.0085(10) C31 0.0432(14) 0.0251(11) 0.0716(19) -0.0123(12) -0.0329(14) 0.0146(10) C32 0.0338(12) 0.0272(11) 0.0595(16) -0.0121(11) -0.0216(12) 0.0080(9) N33 0.0527(14) 0.0308(10) 0.0641(15) 0.0098(11) -0.0276(13) 0.0015(10) O34 0.0550(12) 0.0458(11) 0.0658(14) 0.0125(11) -0.0171(11) 0.0092(10) O35 0.0797(19) 0.0540(15) 0.117(2) 0.0473(16) -0.0133(18) 0.0138(13) O36 0.0408(11) 0.0467(12) 0.0820(16) -0.0054(11) -0.0139(11) 0.0168(9) O100 0.145(4) 0.091(2) 0.166(4) -0.061(3) -0.095(3) 0.038(3) O200 0.065(4) 0.132(7) 0.144(7) 0.054(6) -0.020(4) -0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C13 1.453(3) . ? N1 C2 1.457(3) . ? N1 C15 1.472(3) . ? C2 C3 1.535(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.483(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.484(5) . ? N4 C12 1.491(4) . ? N4 C12A 1.640(7) . ? N4 H4 0.89(4) . ? C5 C6 1.546(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N7 1.459(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 C8 1.458(3) . ? N7 C14 1.459(3) . ? C8 C9 1.535(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N10 1.459(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N10 C11 1.437(5) . ? N10 C26 1.442(3) . ? N10 C11A 1.544(8) . ? C11 C12 1.540(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C11A C12A 1.505(13) . ? C11A H11C 0.9900 . ? C11A H11D 0.9900 . ? C12A H12C 0.9900 . ? C12A H12D 0.9900 . ? C13 C14 1.532(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.523(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.379(5) . ? C16 C21 1.430(4) . ? C17 C18 1.394(4) . ? C17 H17 0.9500 . ? C18 C19 1.404(4) . ? C18 N22 1.445(4) . ? C19 C20 1.375(5) . ? C19 H19 0.9500 . ? C20 C21 1.415(4) . ? C20 H20 0.9500 . ? C21 O25 1.310(4) . ? N22 O23 1.223(4) . ? N22 O24 1.241(4) . ? C26 C27 1.518(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.380(4) . ? C27 C32 1.427(3) . ? C28 C29 1.400(3) . ? C28 H28 0.9500 . ? C29 C30 1.389(4) . ? C29 N33 1.441(4) . ? C30 C31 1.380(5) . ? C30 H30 0.9500 . ? C31 C32 1.410(4) . ? C31 H31 0.9500 . ? C32 O36 1.312(4) . ? N33 O34 1.230(3) . ? N33 O35 1.238(3) . ? O36 H36A 0.8400 . ? 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 C13 N1 C2 117.1(2) . . ? C13 N1 C15 113.2(2) . . ? C2 N1 C15 114.8(2) . . ? N1 C2 C3 109.4(2) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? N4 C3 C2 108.4(2) . . ? N4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? N4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C3 N4 C5 114.3(2) . . ? C3 N4 C12 125.2(3) . . ? C5 N4 C12 103.1(3) . . ? C3 N4 C12A 98.7(4) . . ? C5 N4 C12A 133.4(4) . . ? C12 N4 C12A 31.1(3) . . ? C3 N4 H4 108(3) . . ? C5 N4 H4 91(3) . . ? C12 N4 H4 110(3) . . ? C12A N4 H4 110(3) . . ? N4 C5 C6 108.0(2) . . ? N4 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? N4 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N7 C6 C5 107.6(2) . . ? N7 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? N7 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C8 N7 C6 117.25(19) . . ? C8 N7 C14 117.48(19) . . ? C6 N7 C14 114.9(2) . . ? N7 C8 C9 111.02(19) . . ? N7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N10 C9 C8 111.9(2) . . ? N10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? N10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C11 N10 C26 110.4(3) . . ? C11 N10 C9 128.0(3) . . ? C26 N10 C9 115.18(19) . . ? C11 N10 C11A 24.3(3) . . ? C26 N10 C11A 128.3(5) . . ? C9 N10 C11A 103.8(5) . . ? N10 C11 C12 113.0(4) . . ? N10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? N4 C12 C11 106.8(4) . . ? N4 C12 H12A 110.4 . . ? C11 C12 H12A 110.4 . . ? N4 C12 H12B 110.4 . . ? C11 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12A C11A N10 104.7(7) . . ? C12A C11A H11C 110.8 . . ? N10 C11A H11C 110.8 . . ? C12A C11A H11D 110.8 . . ? N10 C11A H11D 110.8 . . ? H11C C11A H11D 108.9 . . ? C11A C12A N4 107.2(6) . . ? C11A C12A H12C 110.3 . . ? N4 C12A H12C 110.3 . . ? C11A C12A H12D 110.3 . . ? N4 C12A H12D 110.3 . . ? H12C C12A H12D 108.5 . . ? N1 C13 C14 113.8(2) . . ? N1 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? N1 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? N7 C14 C13 112.30(19) . . ? N7 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? N7 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? N1 C15 C16 116.0(2) . . ? N1 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? N1 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C17 C16 C21 119.4(2) . . ? C17 C16 C15 118.7(3) . . ? C21 C16 C15 121.8(3) . . ? C16 C17 C18 120.7(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C19 120.9(3) . . ? C17 C18 N22 119.6(3) . . ? C19 C18 N22 119.5(3) . . ? C20 C19 C18 118.9(3) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C19 C20 C21 121.5(3) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? O25 C21 C20 120.8(3) . . ? O25 C21 C16 120.6(2) . . ? C20 C21 C16 118.5(3) . . ? O23 N22 O24 121.4(3) . . ? O23 N22 C18 118.6(3) . . ? O24 N22 C18 120.0(3) . . ? N10 C26 C27 116.6(2) . . ? N10 C26 H26A 108.1 . . ? C27 C26 H26A 108.1 . . ? N10 C26 H26B 108.1 . . ? C27 C26 H26B 108.1 . . ? H26A C26 H26B 107.3 . . ? C28 C27 C32 118.8(2) . . ? C28 C27 C26 123.2(2) . . ? C32 C27 C26 118.0(3) . . ? C27 C28 C29 120.6(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 121.3(3) . . ? C30 C29 N33 119.3(2) . . ? C28 C29 N33 119.4(2) . . ? C31 C30 C29 118.8(3) . . ? C31 C30 H30 120.6 . . ? C29 C30 H30 120.6 . . ? C30 C31 C32 121.2(2) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? O36 C32 C31 121.1(2) . . ? O36 C32 C27 119.6(3) . . ? C31 C32 C27 119.3(3) . . ? O34 N33 O35 121.4(3) . . ? O34 N33 C29 119.3(2) . . ? O35 N33 C29 119.4(3) . . ? C32 O36 H36A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.178 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.066 data_cu_do2nph _database_code_depnum_ccdc_archive 'CCDC 904675' #TrackingRef 'web_deposit_cif_file_0_RitaDelgado_1353939840.revision for CCDC 904673 - 904676.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H63 Cl Cu2 N12 O19' _chemical_formula_weight 1226.59 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 21.9871(7) _cell_length_b 16.3897(3) _cell_length_c 16.9181(5) _cell_angle_alpha 90.00 _cell_angle_beta 119.4320(10) _cell_angle_gamma 90.00 _cell_volume 5309.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 557 _cell_measurement_theta_min 4.20 _cell_measurement_theta_max 27.10 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 0.937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7536 _exptl_absorpt_correction_T_max 0.9907 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% ? _diffrn_reflns_number 25343 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 30.53 _reflns_number_total 12168 _reflns_number_gt 9816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Platon (Speck, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The three crystallisation water molecules were refined with restraint on O-H and H...H distances of 0.83 and 1.33 A respectively. The CLO4- counter-ion was refined over two tetrahedral positions with restraints on Cl-O and O...O distances in order to reproduce an ideal tetrahedral geometry. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0062(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(10) _refine_ls_number_reflns 12168 _refine_ls_number_parameters 762 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1946 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group CuA Cu 0.09443(4) 0.97630(4) 0.75362(4) 0.01378(17) Uani 1 d . . . N1A N 0.1625(3) 1.0030(3) 0.8858(4) 0.0212(12) Uani 1 d . . . C2A C 0.2308(4) 0.9630(4) 0.9099(5) 0.0279(16) Uani 1 d . . . H2A H 0.2537 0.9440 0.9736 0.033 Uiso 1 calc R . . H2B H 0.2622 1.0029 0.9039 0.033 Uiso 1 calc R . . C3A C 0.2182(4) 0.8911(5) 0.8470(5) 0.0308(17) Uani 1 d . . . H3A H 0.2634 0.8691 0.8568 0.037 Uiso 1 calc R . . H3B H 0.1934 0.8472 0.8598 0.037 Uiso 1 calc R . . N4A N 0.1757(3) 0.9192(3) 0.7521(4) 0.0179(11) Uani 1 d . . . H4A H 0.2009 0.9560 0.7376 0.021 Uiso 1 calc R . . C5A C 0.1483(4) 0.8523(4) 0.6847(4) 0.0215(13) Uani 1 d . . . H5A H 0.1808 0.8054 0.7067 0.026 Uiso 1 calc R . . H5B H 0.1440 0.8711 0.6265 0.026 Uiso 1 calc R . . C6A C 0.0773(4) 0.8265(4) 0.6704(4) 0.0207(13) Uani 1 d . . . H6A H 0.0552 0.7880 0.6187 0.025 Uiso 1 calc R . . H6B H 0.0828 0.7983 0.7253 0.025 Uiso 1 calc R . . N7A N 0.0317(3) 0.9003(3) 0.6514(3) 0.0138(10) Uani 1 d . . . C8A C -0.0305(3) 0.8809(4) 0.6619(4) 0.0188(13) Uani 1 d . . . H8A H -0.0463 0.8244 0.6414 0.023 Uiso 1 calc R . . H8B H -0.0693 0.9186 0.6241 0.023 Uiso 1 calc R . . C9A C -0.0104(4) 0.8902(4) 0.7618(5) 0.0266(15) Uani 1 d . . . H9A H -0.0520 0.8832 0.7693 0.032 Uiso 1 calc R . . H9B H 0.0247 0.8485 0.7990 0.032 Uiso 1 calc R . . N10A N 0.0191(3) 0.9734(4) 0.7903(4) 0.0240(13) Uani 1 d . . . H10A H -0.0148 1.0126 0.7585 0.029 Uiso 1 calc R . . C11A C 0.0517(5) 0.9876(5) 0.8905(5) 0.0358(19) Uani 1 d . . . H11A H 0.0280 0.9538 0.9157 0.043 Uiso 1 calc R . . H11B H 0.0466 1.0457 0.9024 0.043 Uiso 1 calc R . . C12A C 0.1290(5) 0.9650(5) 0.9360(5) 0.0336(19) Uani 1 d . . . H12A H 0.1530 0.9844 0.9996 0.040 Uiso 1 calc R . . H12B H 0.1340 0.9049 0.9365 0.040 Uiso 1 calc R . . C13A C 0.1694(4) 1.0936(4) 0.9009(5) 0.0259(15) Uani 1 d . . . H13A H 0.2023 1.1046 0.9658 0.031 Uiso 1 calc R . . H13B H 0.1234 1.1165 0.8864 0.031 Uiso 1 calc R . . C14A C 0.1952(3) 1.1358(4) 0.8435(4) 0.0185(12) Uani 1 d . . . C15A C 0.2559(4) 1.1813(4) 0.8850(4) 0.0183(12) Uani 1 d . . . H15A H 0.2819 1.1841 0.9494 0.022 Uiso 1 calc R . . C16A C 0.2791(3) 1.2229(4) 0.8337(4) 0.0191(13) Uani 1 d . . . C17A C 0.2418(4) 1.2182(4) 0.7390(4) 0.0219(13) Uani 1 d . . . H17A H 0.2580 1.2468 0.7040 0.026 Uiso 1 calc R . . C18A C 0.1824(3) 1.1728(4) 0.6967(4) 0.0184(12) Uani 1 d . . . H18A H 0.1586 1.1688 0.6324 0.022 Uiso 1 calc R . . C19A C 0.1551(4) 1.1315(4) 0.7459(4) 0.0186(13) Uani 1 d . . . N20A N 0.3390(3) 1.2758(3) 0.8776(4) 0.0234(12) Uani 1 d . . . O21A O 0.3560(3) 1.3177(4) 0.8319(4) 0.0371(14) Uani 1 d . . . O22A O 0.3721(3) 1.2776(3) 0.9622(4) 0.0312(12) Uani 1 d . . . O23A O 0.0972(2) 1.0917(3) 0.7044(3) 0.0197(9) Uani 1 d . . . C24A C 0.0098(4) 0.9376(4) 0.5598(4) 0.0161(12) Uani 1 d . . . H24A H 0.0521 0.9475 0.5546 0.019 Uiso 1 calc R . . H24B H -0.0120 0.9913 0.5566 0.019 Uiso 1 calc R . . C25A C -0.0408(4) 0.8866(4) 0.4796(4) 0.0176(12) Uani 1 d . . . C26A C -0.1121(4) 0.9007(4) 0.4396(4) 0.0193(13) Uani 1 d . . . H26A H -0.1291 0.9416 0.4636 0.023 Uiso 1 calc R . . C27A C -0.1587(4) 0.8559(4) 0.3651(5) 0.0220(13) Uani 1 d . . . C28A C -0.1360(4) 0.7944(4) 0.3280(4) 0.0221(14) Uani 1 d . . . H28A H -0.1686 0.7629 0.2780 0.027 Uiso 1 calc R . . C29A C -0.0664(4) 0.7811(4) 0.3650(4) 0.0235(14) Uani 1 d . . . H29A H -0.0507 0.7398 0.3397 0.028 Uiso 1 calc R . . C30A C -0.0155(4) 0.8271(4) 0.4411(4) 0.0188(12) Uani 1 d . . . N31A N -0.2321(3) 0.8740(4) 0.3230(4) 0.0287(14) Uani 1 d . . . O32A O -0.2526(3) 0.9232(3) 0.3591(4) 0.0414(15) Uani 1 d . . . O33A O -0.2721(3) 0.8397(4) 0.2510(4) 0.0416(15) Uani 1 d . . . O34A O 0.0515(3) 0.8178(3) 0.4737(3) 0.0232(10) Uani 1 d . . . CuB Cu 0.54982(4) 0.99046(4) 0.66010(4) 0.01334(16) Uani 1 d . . . N1B N 0.4879(3) 1.0283(3) 0.5305(4) 0.0179(11) Uani 1 d . . . C2B C 0.4215(4) 0.9812(4) 0.4934(5) 0.0262(15) Uani 1 d . . . H2C H 0.4031 0.9711 0.4278 0.031 Uiso 1 calc R . . H2D H 0.3863 1.0134 0.5004 0.031 Uiso 1 calc R . . C3B C 0.4337(4) 0.9013(4) 0.5423(4) 0.0237(15) Uani 1 d . . . H3C H 0.3886 0.8736 0.5234 0.028 Uiso 1 calc R . . H3D H 0.4630 0.8653 0.5278 0.028 Uiso 1 calc R . . N4B N 0.4694(3) 0.9185(3) 0.6410(4) 0.0202(11) Uani 1 d . . . H4B H 0.4397 0.9469 0.6557 0.024 Uiso 1 calc R . . C5B C 0.4975(4) 0.8450(4) 0.6999(4) 0.0228(14) Uani 1 d . . . H5C H 0.4696 0.7965 0.6674 0.027 Uiso 1 calc R . . H5D H 0.4944 0.8524 0.7558 0.027 Uiso 1 calc R . . C6B C 0.5732(4) 0.8324(4) 0.7243(4) 0.0210(13) Uani 1 d . . . H6C H 0.5946 0.7901 0.7721 0.025 Uiso 1 calc R . . H6D H 0.5753 0.8131 0.6703 0.025 Uiso 1 calc R . . N7B N 0.6132(3) 0.9108(3) 0.7577(4) 0.0163(10) Uani 1 d . . . C8B C 0.6802(4) 0.9074(4) 0.7566(4) 0.0219(13) Uani 1 d . . . H8C H 0.7005 0.8520 0.7737 0.026 Uiso 1 calc R . . H8D H 0.7137 0.9466 0.8012 0.026 Uiso 1 calc R . . C9B C 0.6678(4) 0.9285(4) 0.6614(4) 0.0250(14) Uani 1 d . . . H9C H 0.7128 0.9327 0.6616 0.030 Uiso 1 calc R . . H9D H 0.6390 0.8859 0.6174 0.030 Uiso 1 calc R . . N10B N 0.6310(3) 1.0075(4) 0.6368(4) 0.0204(11) Uani 1 d . . . H10B H 0.6602 1.0484 0.6745 0.024 Uiso 1 calc R . . C11B C 0.6033(4) 1.0305(5) 0.5394(5) 0.0318(17) Uani 1 d . . . H11C H 0.6314 1.0038 0.5157 0.038 Uiso 1 calc R . . H11D H 0.6068 1.0903 0.5344 0.038 Uiso 1 calc R . . C12B C 0.5280(4) 1.0043(5) 0.4843(5) 0.0274(15) Uani 1 d . . . H12C H 0.5068 1.0299 0.4236 0.033 Uiso 1 calc R . . H12D H 0.5257 0.9443 0.4761 0.033 Uiso 1 calc R . . C13B C 0.4762(4) 1.1175(4) 0.5244(4) 0.0209(13) Uani 1 d . . . H13C H 0.4456 1.1326 0.4600 0.025 Uiso 1 calc R . . H13D H 0.5215 1.1456 0.5459 0.025 Uiso 1 calc R . . C14B C 0.4434(3) 1.1470(4) 0.5789(4) 0.0155(12) Uani 1 d . . . C15B C 0.3817(3) 1.1897(4) 0.5381(4) 0.0191(13) Uani 1 d . . . H15B H 0.3580 1.1975 0.4742 0.023 Uiso 1 calc R . . C16B C 0.3534(3) 1.2216(4) 0.5888(5) 0.0210(13) Uani 1 d . . . C17B C 0.3863(4) 1.2103(4) 0.6834(4) 0.0224(13) Uani 1 d . . . H17B H 0.3661 1.2321 0.7172 0.027 Uiso 1 calc R . . C18B C 0.4478(4) 1.1677(4) 0.7263(4) 0.0205(13) Uani 1 d . . . H18B H 0.4698 1.1598 0.7901 0.025 Uiso 1 calc R . . C19B C 0.4790(3) 1.1351(4) 0.6771(4) 0.0158(12) Uani 1 d . . . N20B N 0.2906(3) 1.2703(4) 0.5436(4) 0.0282(13) Uani 1 d . . . O21B O 0.2720(3) 1.3099(4) 0.5894(4) 0.0440(16) Uani 1 d . . . O22B O 0.2586(3) 1.2716(3) 0.4601(4) 0.0353(13) Uani 1 d . . . O23B O 0.5398(3) 1.0979(3) 0.7190(3) 0.0208(10) Uani 1 d . . . C24B C 0.6250(4) 0.9358(3) 0.8490(4) 0.0156(12) Uani 1 d . . . H24C H 0.5796 0.9343 0.8481 0.019 Uiso 1 calc R . . H24D H 0.6415 0.9930 0.8601 0.019 Uiso 1 calc R . . C25B C 0.6769(3) 0.8839(4) 0.9278(4) 0.0151(12) Uani 1 d . . . C26B C 0.7465(4) 0.9072(4) 0.9772(4) 0.0194(13) Uani 1 d . . . H26B H 0.7623 0.9547 0.9605 0.023 Uiso 1 calc R . . C27B C 0.7926(4) 0.8610(4) 1.0509(4) 0.0224(14) Uani 1 d . . . C28B C 0.7709(4) 0.7921(4) 1.0770(5) 0.0244(15) Uani 1 d . . . H28B H 0.8037 0.7603 1.1267 0.029 Uiso 1 calc R . . C29B C 0.7017(4) 0.7696(4) 1.0311(4) 0.0198(13) Uani 1 d . . . H29B H 0.6865 0.7231 1.0504 0.024 Uiso 1 calc R . . C30B C 0.6535(4) 0.8149(4) 0.9561(4) 0.0188(13) Uani 1 d . . . N31B N 0.8657(4) 0.8861(4) 1.1022(4) 0.0325(15) Uani 1 d . . . O32B O 0.8837(3) 0.9473(4) 1.0774(4) 0.0502(18) Uani 1 d . . . O33B O 0.9063(3) 0.8447(5) 1.1667(4) 0.056(2) Uani 1 d . . . O34B O 0.5868(3) 0.7969(3) 0.9121(3) 0.0240(10) Uani 1 d . . . H34B H 0.5787 0.7590 0.9391 0.029 Uiso 1 calc R . . O100 O 0.0536(4) 1.3014(3) 0.4882(4) 0.0408(14) Uani 1 d D . . H101 H 0.075(4) 1.306(5) 0.460(6) 0.049 Uiso 1 d D . . H102 H 0.047(5) 1.2516(13) 0.490(6) 0.049 Uiso 1 d D . . O200 O 0.0141(3) 1.1476(3) 0.5258(3) 0.0330(12) Uani 1 d D . . H201 H 0.041(3) 1.135(5) 0.5794(18) 0.040 Uiso 1 d D . . H202 H -0.023(2) 1.162(5) 0.523(5) 0.040 Uiso 1 d D . . O300 O 0.6119(3) 1.1982(4) 0.8695(4) 0.0469(16) Uani 1 d D . . H301 H 0.6544(12) 1.205(5) 0.888(6) 0.056 Uiso 1 d D . . H302 H 0.609(4) 1.152(3) 0.888(7) 0.056 Uiso 1 d D . . Cl Cl 0.82500(11) 0.55187(10) 1.20211(13) 0.0269(3) Uani 1 d D . . O11 O 0.7972(9) 0.4917(7) 1.2357(13) 0.068(5) Uani 0.68(3) d PD A 1 O21 O 0.8295(8) 0.5237(12) 1.1279(10) 0.098(9) Uani 0.68(3) d PD A 1 O31 O 0.7908(8) 0.6236(6) 1.1906(14) 0.080(6) Uani 0.68(3) d PD A 1 O41 O 0.8960(6) 0.5624(15) 1.2708(7) 0.095(7) Uani 0.68(3) d PD A 1 O12 O 0.7647(13) 0.5031(15) 1.176(3) 0.057(10) Uani 0.32(3) d PD A 2 O22 O 0.8832(14) 0.506(2) 1.237(3) 0.083(15) Uani 0.32(3) d PD A 2 O32 O 0.8271(18) 0.610(3) 1.263(3) 0.16(3) Uani 0.32(3) d PD A 2 O42 O 0.8152(15) 0.593(3) 1.123(2) 0.13(2) Uani 0.32(3) d PD 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 CuA 0.0125(4) 0.0157(3) 0.0121(3) -0.0020(3) 0.0052(3) -0.0013(3) N1A 0.024(3) 0.020(3) 0.017(3) 0.002(2) 0.008(2) -0.003(2) C2A 0.025(4) 0.026(3) 0.019(3) 0.002(3) 0.000(3) -0.003(3) C3A 0.022(4) 0.028(4) 0.027(4) 0.009(3) 0.000(3) 0.008(3) N4A 0.012(3) 0.020(3) 0.016(2) 0.0011(19) 0.003(2) 0.005(2) C5A 0.020(3) 0.022(3) 0.018(3) 0.001(2) 0.005(2) 0.012(3) C6A 0.024(3) 0.016(3) 0.017(3) -0.004(2) 0.007(3) -0.001(3) N7A 0.012(3) 0.016(2) 0.010(2) -0.0027(18) 0.003(2) -0.0001(18) C8A 0.013(3) 0.027(3) 0.014(3) -0.008(2) 0.005(2) -0.010(3) C9A 0.023(3) 0.035(4) 0.026(3) -0.008(3) 0.016(3) -0.016(3) N10A 0.026(3) 0.028(3) 0.021(3) -0.009(2) 0.015(2) -0.008(2) C11A 0.043(5) 0.047(5) 0.035(4) -0.026(3) 0.032(4) -0.024(4) C12A 0.047(5) 0.037(4) 0.018(3) -0.002(3) 0.017(3) -0.017(4) C13A 0.029(4) 0.027(3) 0.023(3) -0.005(3) 0.013(3) -0.010(3) C14A 0.015(3) 0.021(3) 0.015(3) -0.002(2) 0.004(2) -0.001(2) C15A 0.019(3) 0.015(3) 0.021(3) -0.002(2) 0.010(3) -0.001(2) C16A 0.011(3) 0.017(3) 0.024(3) -0.001(2) 0.005(3) -0.002(2) C17A 0.021(3) 0.023(3) 0.028(3) 0.007(2) 0.016(3) 0.006(3) C18A 0.015(3) 0.022(3) 0.017(3) 0.002(2) 0.006(2) -0.001(2) C19A 0.020(3) 0.012(3) 0.022(3) -0.001(2) 0.009(3) 0.003(2) N20A 0.015(3) 0.016(2) 0.039(3) -0.001(2) 0.013(3) -0.001(2) O21A 0.037(3) 0.039(3) 0.041(3) -0.004(2) 0.024(3) -0.017(3) O22A 0.021(3) 0.034(3) 0.031(3) -0.003(2) 0.007(2) -0.005(2) O23A 0.014(2) 0.019(2) 0.017(2) 0.0021(16) 0.0002(18) -0.0023(18) C24A 0.017(3) 0.016(3) 0.016(3) -0.002(2) 0.009(2) -0.000(2) C25A 0.017(3) 0.017(3) 0.016(3) -0.003(2) 0.007(3) -0.003(2) C26A 0.019(3) 0.018(3) 0.021(3) -0.004(2) 0.010(3) 0.004(2) C27A 0.017(3) 0.024(3) 0.020(3) 0.002(2) 0.005(3) 0.003(3) C28A 0.021(3) 0.025(3) 0.009(3) 0.001(2) -0.001(2) 0.004(3) C29A 0.030(4) 0.027(3) 0.010(2) -0.007(2) 0.007(3) -0.001(3) C30A 0.019(3) 0.020(3) 0.017(3) 0.001(2) 0.009(2) 0.005(3) N31A 0.018(3) 0.025(3) 0.029(3) -0.001(2) 0.000(2) 0.002(2) O32A 0.023(3) 0.034(3) 0.048(3) -0.012(2) 0.003(3) 0.013(2) O33A 0.026(3) 0.046(3) 0.033(3) -0.008(3) -0.001(3) 0.005(3) O34A 0.022(2) 0.026(2) 0.024(2) -0.0075(18) 0.013(2) 0.004(2) CuB 0.0112(3) 0.0146(3) 0.0142(3) 0.0014(3) 0.0062(3) -0.0004(3) N1B 0.013(3) 0.022(3) 0.014(2) -0.0031(19) 0.003(2) 0.002(2) C2B 0.019(3) 0.025(3) 0.027(3) -0.005(3) 0.005(3) 0.001(3) C3B 0.017(3) 0.024(3) 0.021(3) -0.010(3) 0.002(3) -0.005(3) N4B 0.015(3) 0.021(3) 0.025(3) -0.003(2) 0.009(2) -0.003(2) C5B 0.025(3) 0.021(3) 0.020(3) 0.003(2) 0.010(3) -0.009(3) C6B 0.029(4) 0.014(3) 0.023(3) 0.004(2) 0.015(3) 0.001(3) N7B 0.017(3) 0.017(2) 0.015(2) 0.0009(19) 0.008(2) -0.000(2) C8B 0.022(3) 0.027(3) 0.022(3) 0.004(2) 0.016(3) 0.008(3) C9B 0.025(4) 0.034(4) 0.020(3) 0.004(3) 0.014(3) 0.007(3) N10B 0.017(3) 0.025(3) 0.019(2) 0.003(2) 0.009(2) -0.001(2) C11B 0.033(4) 0.039(4) 0.033(4) 0.014(3) 0.023(3) 0.007(3) C12B 0.031(4) 0.032(4) 0.016(3) 0.002(3) 0.009(3) 0.012(3) C13B 0.027(3) 0.018(3) 0.020(3) 0.007(2) 0.013(3) 0.006(3) C14B 0.015(3) 0.015(3) 0.018(3) -0.003(2) 0.009(2) -0.003(2) C15B 0.015(3) 0.018(3) 0.015(3) -0.002(2) 0.001(2) -0.002(2) C16B 0.012(3) 0.023(3) 0.025(3) -0.002(2) 0.007(3) -0.002(2) C17B 0.019(3) 0.028(3) 0.022(3) -0.001(2) 0.012(3) 0.000(3) C18B 0.017(3) 0.024(3) 0.019(3) -0.001(2) 0.008(3) -0.003(3) C19B 0.012(3) 0.015(3) 0.014(3) -0.002(2) 0.001(2) 0.000(2) N20B 0.021(3) 0.030(3) 0.035(3) 0.002(3) 0.014(3) 0.003(3) O21B 0.048(4) 0.054(4) 0.044(3) 0.015(3) 0.033(3) 0.029(3) O22B 0.020(3) 0.042(3) 0.028(3) -0.004(2) -0.000(2) 0.009(2) O23B 0.019(2) 0.021(2) 0.017(2) -0.0033(16) 0.0049(19) 0.0046(18) C24B 0.023(3) 0.014(3) 0.016(3) 0.004(2) 0.014(3) -0.000(2) C25B 0.019(3) 0.016(3) 0.012(3) 0.002(2) 0.009(2) -0.002(2) C26B 0.025(3) 0.019(3) 0.016(3) -0.000(2) 0.012(3) -0.002(3) C27B 0.021(3) 0.031(3) 0.013(3) 0.001(2) 0.006(3) -0.003(3) C28B 0.029(4) 0.027(3) 0.020(3) 0.009(3) 0.014(3) 0.003(3) C29B 0.027(3) 0.021(3) 0.016(3) 0.001(2) 0.015(3) -0.003(3) C30B 0.027(3) 0.019(3) 0.020(3) -0.000(2) 0.019(3) -0.001(3) N31B 0.024(3) 0.042(4) 0.025(3) 0.006(3) 0.008(3) -0.003(3) O32B 0.032(3) 0.042(3) 0.057(4) 0.017(3) 0.006(3) -0.014(3) O33B 0.026(3) 0.086(5) 0.031(3) 0.032(3) -0.005(3) -0.006(3) O34B 0.022(2) 0.026(2) 0.026(2) 0.0070(18) 0.013(2) -0.005(2) O100 0.059(4) 0.026(3) 0.048(3) -0.005(2) 0.035(3) -0.004(3) O200 0.022(3) 0.040(3) 0.028(3) 0.013(2) 0.005(2) 0.010(2) O300 0.025(3) 0.070(4) 0.042(3) -0.022(3) 0.014(3) -0.009(3) Cl 0.0247(7) 0.0291(8) 0.0291(7) -0.0016(7) 0.0149(6) -0.0024(7) O11 0.074(11) 0.042(6) 0.104(13) 0.020(7) 0.056(11) -0.004(6) O21 0.066(11) 0.172(19) 0.080(12) -0.086(13) 0.054(10) -0.057(12) O31 0.083(11) 0.037(6) 0.164(17) 0.037(8) 0.094(12) 0.025(6) O41 0.040(7) 0.19(2) 0.035(6) 0.012(9) 0.001(5) -0.043(10) O12 0.043(17) 0.034(13) 0.11(3) -0.033(15) 0.049(19) -0.021(12) O22 0.06(2) 0.08(2) 0.12(4) 0.06(2) 0.05(2) 0.060(19) O32 0.10(4) 0.18(4) 0.17(4) -0.16(4) 0.06(3) -0.02(3) O42 0.07(2) 0.22(6) 0.08(2) 0.09(3) 0.010(19) 0.06(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 CuA N7A 2.025(5) . ? CuA N4A 2.028(6) . ? CuA N1A 2.035(6) . ? CuA N10A 2.034(6) . ? CuA O23A 2.079(4) . ? N1A C2A 1.501(10) . ? N1A C13A 1.501(8) . ? N1A C12A 1.505(9) . ? C2A C3A 1.519(11) . ? C2A H2A 0.9900 . ? C2A H2B 0.9900 . ? C3A N4A 1.480(9) . ? C3A H3A 0.9900 . ? C3A H3B 0.9900 . ? N4A C5A 1.480(8) . ? N4A H4A 0.9300 . ? C5A C6A 1.517(10) . ? C5A H5A 0.9900 . ? C5A H5B 0.9900 . ? C6A N7A 1.501(8) . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? N7A C8A 1.497(8) . ? N7A C24A 1.508(8) . ? C8A C9A 1.530(9) . ? C8A H8A 0.9900 . ? C8A H8B 0.9900 . ? C9A N10A 1.486(9) . ? C9A H9A 0.9900 . ? C9A H9B 0.9900 . ? N10A C11A 1.500(9) . ? N10A H10A 0.9300 . ? C11A C12A 1.528(12) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.512(9) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.381(9) . ? C14A C19A 1.442(9) . ? C15A C16A 1.383(9) . ? C15A H15A 0.9500 . ? C16A C17A 1.398(9) . ? C16A N20A 1.442(8) . ? C17A C18A 1.361(9) . ? C17A H17A 0.9500 . ? C18A C19A 1.415(9) . ? C18A H18A 0.9500 . ? C19A O23A 1.289(8) . ? N20A O21A 1.222(8) . ? N20A O22A 1.247(8) . ? C24A C25A 1.515(9) . ? C24A H24A 0.9900 . ? C24A H24B 0.9900 . ? C25A C26A 1.389(9) . ? C25A C30A 1.428(9) . ? C26A C27A 1.381(9) . ? C26A H26A 0.9500 . ? C27A C28A 1.402(10) . ? C27A N31A 1.440(9) . ? C28A C29A 1.356(10) . ? C28A H28A 0.9500 . ? C29A C30A 1.437(9) . ? C29A H29A 0.9500 . ? C30A O34A 1.304(8) . ? N31A O32A 1.224(8) . ? N31A O33A 1.233(8) . ? CuB N4B 2.015(6) . ? CuB N1B 2.027(6) . ? CuB N7B 2.028(5) . ? CuB N10B 2.027(6) . ? CuB O23B 2.086(4) . ? N1B C13B 1.479(8) . ? N1B C12B 1.490(9) . ? N1B C2B 1.490(9) . ? C2B C3B 1.502(10) . ? C2B H2C 0.9900 . ? C2B H2D 0.9900 . ? C3B N4B 1.482(8) . ? C3B H3C 0.9900 . ? C3B H3D 0.9900 . ? N4B C5B 1.490(8) . ? N4B H4B 0.9300 . ? C5B C6B 1.518(10) . ? C5B H5C 0.9900 . ? C5B H5D 0.9900 . ? C6B N7B 1.503(8) . ? C6B H6C 0.9900 . ? C6B H6D 0.9900 . ? N7B C8B 1.484(8) . ? N7B C24B 1.492(8) . ? C8B C9B 1.534(9) . ? C8B H8C 0.9900 . ? C8B H8D 0.9900 . ? C9B N10B 1.473(9) . ? C9B H9C 0.9900 . ? C9B H9D 0.9900 . ? N10B C11B 1.497(9) . ? N10B H10B 0.9300 . ? C11B C12B 1.508(11) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.502(9) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.375(9) . ? C14B C19B 1.460(9) . ? C15B C16B 1.385(9) . ? C15B H15B 0.9500 . ? C16B C17B 1.407(9) . ? C16B N20B 1.447(9) . ? C17B C18B 1.370(10) . ? C17B H17B 0.9500 . ? C18B C19B 1.418(9) . ? C18B H18B 0.9500 . ? C19B O23B 1.316(8) . ? N20B O21B 1.225(8) . ? N20B O22B 1.231(8) . ? C24B C25B 1.520(8) . ? C24B H24C 0.9900 . ? C24B H24D 0.9900 . ? C25B C26B 1.389(9) . ? C25B C30B 1.418(8) . ? C26B C27B 1.384(9) . ? C26B H26B 0.9500 . ? C27B C28B 1.380(9) . ? C27B N31B 1.460(10) . ? C28B C29B 1.377(10) . ? C28B H28B 0.9500 . ? C29B C30B 1.402(9) . ? C29B H29B 0.9500 . ? C30B O34B 1.313(8) . ? N31B O33B 1.221(8) . ? N31B O32B 1.226(8) . ? O34B H34B 0.8400 . ? O100 H101 0.832(10) . ? O100 H102 0.832(10) . ? O200 H201 0.830(10) . ? O200 H202 0.829(10) . ? O300 H301 0.834(10) . ? O300 H302 0.840(10) . ? Cl O22 1.347(14) . ? Cl O31 1.357(9) . ? Cl O21 1.386(9) . ? Cl O32 1.388(14) . ? Cl O42 1.408(16) . ? Cl O11 1.418(9) . ? Cl O12 1.421(14) . ? Cl O41 1.427(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7A CuA N4A 86.5(2) . . ? N7A CuA N1A 153.5(2) . . ? N4A CuA N1A 86.4(2) . . ? N7A CuA N10A 86.1(2) . . ? N4A CuA N10A 147.9(2) . . ? N1A CuA N10A 86.5(3) . . ? N7A CuA O23A 111.06(19) . . ? N4A CuA O23A 102.5(2) . . ? N1A CuA O23A 95.4(2) . . ? N10A CuA O23A 109.3(2) . . ? C2A N1A C13A 112.4(6) . . ? C2A N1A C12A 111.6(6) . . ? C13A N1A C12A 110.5(6) . . ? C2A N1A CuA 107.6(4) . . ? C13A N1A CuA 111.0(4) . . ? C12A N1A CuA 103.4(5) . . ? N1A C2A C3A 109.6(6) . . ? N1A C2A H2A 109.8 . . ? C3A C2A H2A 109.8 . . ? N1A C2A H2B 109.8 . . ? C3A C2A H2B 109.8 . . ? H2A C2A H2B 108.2 . . ? N4A C3A C2A 108.6(6) . . ? N4A C3A H3A 110.0 . . ? C2A C3A H3A 110.0 . . ? N4A C3A H3B 110.0 . . ? C2A C3A H3B 110.0 . . ? H3A C3A H3B 108.4 . . ? C5A N4A C3A 114.0(5) . . ? C5A N4A CuA 108.9(4) . . ? C3A N4A CuA 102.7(4) . . ? C5A N4A H4A 110.3 . . ? C3A N4A H4A 110.3 . . ? CuA N4A H4A 110.3 . . ? N4A C5A C6A 109.1(5) . . ? N4A C5A H5A 109.9 . . ? C6A C5A H5A 109.9 . . ? N4A C5A H5B 109.9 . . ? C6A C5A H5B 109.9 . . ? H5A C5A H5B 108.3 . . ? N7A C6A C5A 109.6(5) . . ? N7A C6A H6A 109.8 . . ? C5A C6A H6A 109.8 . . ? N7A C6A H6B 109.8 . . ? C5A C6A H6B 109.8 . . ? H6A C6A H6B 108.2 . . ? C8A N7A C6A 110.9(5) . . ? C8A N7A C24A 111.0(5) . . ? C6A N7A C24A 112.9(5) . . ? C8A N7A CuA 107.9(4) . . ? C6A N7A CuA 102.1(4) . . ? C24A N7A CuA 111.5(4) . . ? N7A C8A C9A 109.0(5) . . ? N7A C8A H8A 109.9 . . ? C9A C8A H8A 109.9 . . ? N7A C8A H8B 109.9 . . ? C9A C8A H8B 109.9 . . ? H8A C8A H8B 108.3 . . ? N10A C9A C8A 107.0(5) . . ? N10A C9A H9A 110.3 . . ? C8A C9A H9A 110.3 . . ? N10A C9A H9B 110.3 . . ? C8A C9A H9B 110.3 . . ? H9A C9A H9B 108.6 . . ? C9A N10A C11A 113.5(6) . . ? C9A N10A CuA 102.3(4) . . ? C11A N10A CuA 109.4(5) . . ? C9A N10A H10A 110.4 . . ? C11A N10A H10A 110.4 . . ? CuA N10A H10A 110.4 . . ? N10A C11A C12A 109.1(6) . . ? N10A C11A H11A 109.9 . . ? C12A C11A H11A 109.9 . . ? N10A C11A H11B 109.9 . . ? C12A C11A H11B 109.9 . . ? H11A C11A H11B 108.3 . . ? N1A C12A C11A 110.3(6) . . ? N1A C12A H12A 109.6 . . ? C11A C12A H12A 109.6 . . ? N1A C12A H12B 109.6 . . ? C11A C12A H12B 109.6 . . ? H12A C12A H12B 108.1 . . ? N1A C13A C14A 112.4(6) . . ? N1A C13A H13A 109.1 . . ? C14A C13A H13A 109.1 . . ? N1A C13A H13B 109.1 . . ? C14A C13A H13B 109.1 . . ? H13A C13A H13B 107.8 . . ? C15A C14A C19A 120.2(6) . . ? C15A C14A C13A 119.6(6) . . ? C19A C14A C13A 120.1(6) . . ? C14A C15A C16A 120.6(6) . . ? C14A C15A H15A 119.7 . . ? C16A C15A H15A 119.7 . . ? C15A C16A C17A 120.2(6) . . ? C15A C16A N20A 119.9(6) . . ? C17A C16A N20A 119.8(6) . . ? C18A C17A C16A 120.2(6) . . ? C18A C17A H17A 119.9 . . ? C16A C17A H17A 119.9 . . ? C17A C18A C19A 121.9(6) . . ? C17A C18A H18A 119.1 . . ? C19A C18A H18A 119.1 . . ? O23A C19A C18A 120.9(6) . . ? O23A C19A C14A 122.2(6) . . ? C18A C19A C14A 116.9(6) . . ? O21A N20A O22A 121.7(6) . . ? O21A N20A C16A 119.9(6) . . ? O22A N20A C16A 118.4(6) . . ? C19A O23A CuA 117.2(4) . . ? N7A C24A C25A 114.8(5) . . ? N7A C24A H24A 108.6 . . ? C25A C24A H24A 108.6 . . ? N7A C24A H24B 108.6 . . ? C25A C24A H24B 108.6 . . ? H24A C24A H24B 107.5 . . ? C26A C25A C30A 119.4(6) . . ? C26A C25A C24A 120.0(6) . . ? C30A C25A C24A 120.4(6) . . ? C27A C26A C25A 120.6(6) . . ? C27A C26A H26A 119.7 . . ? C25A C26A H26A 119.7 . . ? C26A C27A C28A 121.6(6) . . ? C26A C27A N31A 119.3(6) . . ? C28A C27A N31A 119.1(6) . . ? C29A C28A C27A 118.6(6) . . ? C29A C28A H28A 120.7 . . ? C27A C28A H28A 120.7 . . ? C28A C29A C30A 122.3(6) . . ? C28A C29A H29A 118.9 . . ? C30A C29A H29A 118.9 . . ? O34A C30A C25A 120.0(6) . . ? O34A C30A C29A 122.6(6) . . ? C25A C30A C29A 117.5(6) . . ? O32A N31A O33A 122.4(7) . . ? O32A N31A C27A 119.2(6) . . ? O33A N31A C27A 118.4(6) . . ? N4B CuB N1B 86.3(2) . . ? N4B CuB N7B 87.2(2) . . ? N1B CuB N7B 154.9(2) . . ? N4B CuB N10B 146.8(2) . . ? N1B CuB N10B 86.3(2) . . ? N7B CuB N10B 85.9(2) . . ? N4B CuB O23B 106.3(2) . . ? N1B CuB O23B 94.9(2) . . ? N7B CuB O23B 110.2(2) . . ? N10B CuB O23B 106.6(2) . . ? C13B N1B C12B 110.7(6) . . ? C13B N1B C2B 112.4(6) . . ? C12B N1B C2B 110.5(6) . . ? C13B N1B CuB 112.3(4) . . ? C12B N1B CuB 103.3(4) . . ? C2B N1B CuB 107.2(4) . . ? N1B C2B C3B 110.3(6) . . ? N1B C2B H2C 109.6 . . ? C3B C2B H2C 109.6 . . ? N1B C2B H2D 109.6 . . ? C3B C2B H2D 109.6 . . ? H2C C2B H2D 108.1 . . ? N4B C3B C2B 107.9(5) . . ? N4B C3B H3C 110.1 . . ? C2B C3B H3C 110.1 . . ? N4B C3B H3D 110.1 . . ? C2B C3B H3D 110.1 . . ? H3C C3B H3D 108.4 . . ? C3B N4B C5B 114.5(5) . . ? C3B N4B CuB 103.3(4) . . ? C5B N4B CuB 108.8(4) . . ? C3B N4B H4B 110.0 . . ? C5B N4B H4B 110.0 . . ? CuB N4B H4B 110.0 . . ? N4B C5B C6B 109.4(5) . . ? N4B C5B H5C 109.8 . . ? C6B C5B H5C 109.8 . . ? N4B C5B H5D 109.8 . . ? C6B C5B H5D 109.8 . . ? H5C C5B H5D 108.2 . . ? N7B C6B C5B 110.3(5) . . ? N7B C6B H6C 109.6 . . ? C5B C6B H6C 109.6 . . ? N7B C6B H6D 109.6 . . ? C5B C6B H6D 109.6 . . ? H6C C6B H6D 108.1 . . ? C8B N7B C24B 110.8(5) . . ? C8B N7B C6B 111.4(5) . . ? C24B N7B C6B 113.3(5) . . ? C8B N7B CuB 107.6(4) . . ? C24B N7B CuB 111.5(4) . . ? C6B N7B CuB 101.7(4) . . ? N7B C8B C9B 109.8(5) . . ? N7B C8B H8C 109.7 . . ? C9B C8B H8C 109.7 . . ? N7B C8B H8D 109.7 . . ? C9B C8B H8D 109.7 . . ? H8C C8B H8D 108.2 . . ? N10B C9B C8B 106.5(5) . . ? N10B C9B H9C 110.4 . . ? C8B C9B H9C 110.4 . . ? N10B C9B H9D 110.4 . . ? C8B C9B H9D 110.4 . . ? H9C C9B H9D 108.6 . . ? C9B N10B C11B 113.7(5) . . ? C9B N10B CuB 103.8(4) . . ? C11B N10B CuB 109.1(5) . . ? C9B N10B H10B 110.0 . . ? C11B N10B H10B 110.0 . . ? CuB N10B H10B 110.0 . . ? N10B C11B C12B 109.8(6) . . ? N10B C11B H11C 109.7 . . ? C12B C11B H11C 109.7 . . ? N10B C11B H11D 109.7 . . ? C12B C11B H11D 109.7 . . ? H11C C11B H11D 108.2 . . ? N1B C12B C11B 110.6(6) . . ? N1B C12B H12C 109.5 . . ? C11B C12B H12C 109.5 . . ? N1B C12B H12D 109.5 . . ? C11B C12B H12D 109.5 . . ? H12C C12B H12D 108.1 . . ? N1B C13B C14B 113.3(5) . . ? N1B C13B H13C 108.9 . . ? C14B C13B H13C 108.9 . . ? N1B C13B H13D 108.9 . . ? C14B C13B H13D 108.9 . . ? H13C C13B H13D 107.7 . . ? C15B C14B C19B 119.0(6) . . ? C15B C14B C13B 120.6(6) . . ? C19B C14B C13B 120.3(6) . . ? C14B C15B C16B 120.9(6) . . ? C14B C15B H15B 119.5 . . ? C16B C15B H15B 119.5 . . ? C15B C16B C17B 121.2(6) . . ? C15B C16B N20B 118.9(6) . . ? C17B C16B N20B 119.9(6) . . ? C18B C17B C16B 119.5(6) . . ? C18B C17B H17B 120.3 . . ? C16B C17B H17B 120.3 . . ? C17B C18B C19B 121.1(6) . . ? C17B C18B H18B 119.4 . . ? C19B C18B H18B 119.4 . . ? O23B C19B C18B 121.0(6) . . ? O23B C19B C14B 120.6(6) . . ? C18B C19B C14B 118.3(6) . . ? O21B N20B O22B 122.5(6) . . ? O21B N20B C16B 119.1(6) . . ? O22B N20B C16B 118.4(6) . . ? C19B O23B CuB 116.9(4) . . ? N7B C24B C25B 115.4(5) . . ? N7B C24B H24C 108.4 . . ? C25B C24B H24C 108.4 . . ? N7B C24B H24D 108.4 . . ? C25B C24B H24D 108.4 . . ? H24C C24B H24D 107.5 . . ? C26B C25B C30B 119.4(6) . . ? C26B C25B C24B 120.3(5) . . ? C30B C25B C24B 120.1(6) . . ? C27B C26B C25B 119.6(6) . . ? C27B C26B H26B 120.2 . . ? C25B C26B H26B 120.2 . . ? C28B C27B C26B 121.4(7) . . ? C28B C27B N31B 119.5(6) . . ? C26B C27B N31B 119.1(6) . . ? C29B C28B C27B 120.0(6) . . ? C29B C28B H28B 120.0 . . ? C27B C28B H28B 120.0 . . ? C28B C29B C30B 120.1(6) . . ? C28B C29B H29B 119.9 . . ? C30B C29B H29B 119.9 . . ? O34B C30B C29B 122.1(6) . . ? O34B C30B C25B 118.5(6) . . ? C29B C30B C25B 119.4(6) . . ? O33B N31B O32B 122.8(7) . . ? O33B N31B C27B 118.9(6) . . ? O32B N31B C27B 118.2(6) . . ? C30B O34B H34B 109.5 . . ? H101 O100 H102 105.8(17) . . ? H201 O200 H202 106.3(17) . . ? H301 O300 H302 104.5(17) . . ? O22 Cl O31 152.7(16) . . ? O22 Cl O21 74.8(15) . . ? O31 Cl O21 116.0(9) . . ? O22 Cl O32 112.3(15) . . ? O31 Cl O32 47.6(19) . . ? O21 Cl O32 156(2) . . ? O22 Cl O42 110.7(14) . . ? O31 Cl O42 68.7(18) . . ? O21 Cl O42 49.2(19) . . ? O32 Cl O42 108.1(14) . . ? O22 Cl O11 86.3(13) . . ? O31 Cl O11 110.1(7) . . ? O21 Cl O11 111.6(8) . . ? O32 Cl O11 92(2) . . ? O42 Cl O11 144.4(16) . . ? O22 Cl O12 111.1(12) . . ? O31 Cl O12 94.4(12) . . ? O21 Cl O12 90.4(13) . . ? O32 Cl O12 107.3(13) . . ? O42 Cl O12 107.0(13) . . ? O11 Cl O12 37.8(13) . . ? O22 Cl O41 44.5(15) . . ? O31 Cl O41 108.6(9) . . ? O21 Cl O41 104.0(8) . . ? O32 Cl O41 71.8(14) . . ? O42 Cl O41 108.1(15) . . ? O11 Cl O41 105.8(7) . . ? O12 Cl O41 143.2(15) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.300 _refine_diff_density_min -1.127 _refine_diff_density_rms 0.291 data_Cu_cb_do2nph _database_code_depnum_ccdc_archive 'CCDC 904676' #TrackingRef 'web_deposit_cif_file_0_RitaDelgado_1353939840.revision for CCDC 904673 - 904676.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H32 Cu N6 O7' _chemical_formula_weight 580.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc 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' _cell_length_a 23.2324(10) _cell_length_b 10.1166(5) _cell_length_c 12.6511(6) _cell_angle_alpha 90.00 _cell_angle_beta 122.370(2) _cell_angle_gamma 90.00 _cell_volume 2511.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 31.50 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8081 _exptl_absorpt_correction_T_max 0.9817 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 0.5 _diffrn_standards_interval_time 40 _diffrn_standards_decay_% ? _diffrn_reflns_number 22481 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 30.53 _reflns_number_total 7236 _reflns_number_gt 6325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Platon (Speck, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0992P)^2^+0.7592P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0243(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.045(15) _refine_ls_number_reflns 7236 _refine_ls_number_parameters 344 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1540 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.28264(2) 0.71934(4) 0.31036(3) 0.01474(14) Uani 1 d . . . N1 N 0.18891(19) 0.6977(3) 0.1579(4) 0.0179(7) Uani 1 d . . . C2 C 0.1996(2) 0.6464(5) 0.0578(4) 0.0222(8) Uani 1 d . . . H2A H 0.1903 0.7181 -0.0026 0.027 Uiso 1 calc R . . H2B H 0.1670 0.5738 0.0118 0.027 Uiso 1 calc R . . C3 C 0.2725(2) 0.5955(4) 0.1130(4) 0.0219(8) Uani 1 d . . . H3A H 0.2798 0.5139 0.1619 0.026 Uiso 1 calc R . . H3B H 0.2802 0.5750 0.0451 0.026 Uiso 1 calc R . . N4 N 0.3203(2) 0.7002(4) 0.1953(4) 0.0193(8) Uani 1 d . . . C5 C 0.3914(2) 0.6603(5) 0.2842(4) 0.0220(8) Uani 1 d . . . H5A H 0.4173 0.6616 0.2426 0.026 Uiso 1 calc R . . H5B H 0.3929 0.5696 0.3148 0.026 Uiso 1 calc R . . C6 C 0.4226(2) 0.7579(4) 0.3937(5) 0.0213(8) Uani 1 d . . . H6A H 0.4673 0.7239 0.4618 0.026 Uiso 1 calc R . . H6B H 0.4305 0.8437 0.3658 0.026 Uiso 1 calc R . . N7 N 0.37704(19) 0.7786(3) 0.4427(4) 0.0189(7) Uani 1 d . . . C8 C 0.3649(2) 0.9191(4) 0.4585(5) 0.0223(9) Uani 1 d . . . H8A H 0.4096 0.9623 0.5140 0.027 Uiso 1 calc R . . H8B H 0.3397 0.9223 0.5014 0.027 Uiso 1 calc R . . C9 C 0.3252(2) 0.9994(4) 0.3370(5) 0.0242(9) Uani 1 d . . . H9A H 0.3073 1.0800 0.3540 0.029 Uiso 1 calc R . . H9B H 0.3573 1.0281 0.3127 0.029 Uiso 1 calc R . . N10 N 0.2684(2) 0.9300(4) 0.2311(4) 0.0227(7) Uani 1 d . . . C11 C 0.2705(3) 0.9286(4) 0.1173(4) 0.0241(8) Uani 1 d . . . H11A H 0.2864 1.0156 0.1069 0.029 Uiso 1 calc R . . H11B H 0.2240 0.9135 0.0436 0.029 Uiso 1 calc R . . C12 C 0.3181(2) 0.8203(4) 0.1233(4) 0.0208(8) Uani 1 d . . . H12A H 0.3031 0.7933 0.0370 0.025 Uiso 1 calc R . . H12B H 0.3648 0.8569 0.1628 0.025 Uiso 1 calc R . . C13 C 0.1998(2) 0.9452(4) 0.2071(5) 0.0227(9) Uani 1 d . . . H13A H 0.1799 1.0295 0.1625 0.027 Uiso 1 calc R . . H13B H 0.2023 0.9486 0.2877 0.027 Uiso 1 calc R . . C14 C 0.1533(2) 0.8286(4) 0.1272(4) 0.0215(8) Uani 1 d . . . H14A H 0.1147 0.8220 0.1394 0.026 Uiso 1 calc R . . H14B H 0.1342 0.8483 0.0377 0.026 Uiso 1 calc R . . C15 C 0.1527(2) 0.5951(4) 0.1854(4) 0.0199(8) Uani 1 d . . . H15A H 0.1796 0.5123 0.2091 0.024 Uiso 1 calc R . . H15B H 0.1081 0.5772 0.1078 0.024 Uiso 1 calc R . . C16 C 0.1406(2) 0.6303(4) 0.2879(4) 0.0174(7) Uani 1 d . . . C17 C 0.0804(2) 0.5879(4) 0.2741(4) 0.0216(8) Uani 1 d . . . H17 H 0.0478 0.5424 0.2001 0.026 Uiso 1 calc R . . C18 C 0.0667(2) 0.6112(4) 0.3674(4) 0.0215(8) Uani 1 d . . . C19 C 0.1135(2) 0.6799(4) 0.4766(4) 0.0227(8) Uani 1 d . . . H19 H 0.1040 0.6950 0.5399 0.027 Uiso 1 calc R . . C20 C 0.1736(2) 0.7255(4) 0.4915(5) 0.0221(8) Uani 1 d . . . H20 H 0.2046 0.7745 0.5643 0.027 Uiso 1 calc R . . C21 C 0.1895(2) 0.6996(4) 0.3979(4) 0.0180(8) Uani 1 d . . . N22 N 0.00704(19) 0.5571(4) 0.3556(4) 0.0256(8) Uani 1 d . . . O23 O -0.03581(18) 0.5026(5) 0.2552(4) 0.0381(9) Uani 1 d . . . O24 O -0.0010(2) 0.5654(4) 0.4441(4) 0.0353(8) Uani 1 d . . . O25 O 0.24713(18) 0.7445(4) 0.4191(3) 0.0215(7) Uani 1 d . . . C26 C 0.4025(2) 0.7062(4) 0.5637(4) 0.0213(8) Uani 1 d . . . H26A H 0.4418 0.7553 0.6318 0.026 Uiso 1 calc R . . H26B H 0.3661 0.7064 0.5820 0.026 Uiso 1 calc R . . C27 C 0.4238(2) 0.5669(4) 0.5655(4) 0.0197(8) Uani 1 d . . . C28 C 0.4898(2) 0.5283(5) 0.6557(4) 0.0245(9) Uani 1 d . . . H28 H 0.5207 0.5905 0.7156 0.029 Uiso 1 calc R . . C29 C 0.5108(2) 0.3975(5) 0.6585(4) 0.0249(9) Uani 1 d . . . C30 C 0.4663(3) 0.3042(5) 0.5715(5) 0.0283(10) Uani 1 d . . . H30 H 0.4811 0.2159 0.5745 0.034 Uiso 1 calc R . . C31 C 0.4011(3) 0.3413(5) 0.4816(5) 0.0273(9) Uani 1 d . . . H31 H 0.3714 0.2783 0.4212 0.033 Uiso 1 calc R . . C32 C 0.3768(2) 0.4725(4) 0.4767(4) 0.0188(8) Uani 1 d . . . N33 N 0.5780(2) 0.3588(5) 0.7513(4) 0.0301(9) Uani 1 d . . . O34 O 0.5972(2) 0.2435(5) 0.7487(5) 0.0439(10) Uani 1 d . . . O35 O 0.6163(2) 0.4388(4) 0.8324(4) 0.0400(9) Uani 1 d . . . O36 O 0.31469(16) 0.5057(3) 0.3931(3) 0.0227(6) Uani 1 d . . . O100 O 0.2360(2) 0.7254(4) 0.8052(4) 0.0375(9) Uani 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 Cu 0.0123(2) 0.0137(2) 0.0182(2) -0.0021(2) 0.00820(17) -0.00254(19) N1 0.0216(17) 0.0140(14) 0.0214(18) -0.0009(12) 0.0138(15) -0.0019(12) C2 0.023(2) 0.030(2) 0.0137(19) -0.0053(15) 0.0098(16) -0.0063(17) C3 0.028(2) 0.0219(19) 0.021(2) -0.0039(15) 0.0168(18) -0.0022(16) N4 0.0235(19) 0.0165(15) 0.021(2) 0.0013(14) 0.0137(17) -0.0015(14) C5 0.019(2) 0.026(2) 0.025(2) 0.0022(17) 0.0136(18) 0.0035(16) C6 0.020(2) 0.0188(17) 0.030(2) -0.0023(16) 0.0165(18) -0.0023(14) N7 0.0185(17) 0.0160(16) 0.0249(19) -0.0010(13) 0.0135(15) -0.0017(13) C8 0.028(2) 0.0120(17) 0.031(2) -0.0066(16) 0.018(2) -0.0067(15) C9 0.021(2) 0.0142(17) 0.038(3) -0.0016(16) 0.016(2) -0.0011(14) N10 0.0255(19) 0.0192(16) 0.029(2) 0.0004(14) 0.0180(16) 0.0008(13) C11 0.027(2) 0.0229(19) 0.025(2) 0.0067(16) 0.0158(19) 0.0013(16) C12 0.024(2) 0.0196(17) 0.022(2) 0.0012(15) 0.0142(18) -0.0016(15) C13 0.021(2) 0.0188(19) 0.032(2) 0.0013(17) 0.0164(19) 0.0022(16) C14 0.0155(19) 0.0202(18) 0.027(2) 0.0056(16) 0.0100(17) 0.0042(15) C15 0.0188(19) 0.0178(17) 0.023(2) -0.0021(15) 0.0111(17) -0.0041(14) C16 0.0183(19) 0.0156(16) 0.020(2) 0.0026(14) 0.0110(16) -0.0005(14) C17 0.0176(19) 0.0212(19) 0.022(2) 0.0042(15) 0.0080(17) 0.0005(15) C18 0.0167(18) 0.0215(18) 0.026(2) 0.0044(16) 0.0117(17) -0.0002(15) C19 0.027(2) 0.0184(18) 0.027(2) -0.0007(15) 0.018(2) -0.0015(15) C20 0.026(2) 0.0205(18) 0.026(2) -0.0058(15) 0.0178(19) -0.0054(15) C21 0.023(2) 0.0127(16) 0.022(2) -0.0017(14) 0.0145(17) -0.0030(13) N22 0.0183(18) 0.0280(19) 0.032(2) 0.0071(16) 0.0141(17) -0.0025(14) O23 0.0222(18) 0.057(2) 0.0268(19) 0.0043(17) 0.0072(15) -0.0131(17) O24 0.0328(19) 0.042(2) 0.044(2) -0.0039(16) 0.0286(18) -0.0089(16) O25 0.0181(16) 0.0240(14) 0.0244(18) -0.0055(14) 0.0127(14) -0.0047(13) C26 0.024(2) 0.0211(18) 0.016(2) 0.0013(14) 0.0094(17) -0.0013(15) C27 0.0193(19) 0.0200(18) 0.021(2) -0.0018(14) 0.0116(17) -0.0037(15) C28 0.021(2) 0.029(2) 0.023(2) 0.0003(16) 0.0111(18) -0.0061(17) C29 0.019(2) 0.029(2) 0.025(2) 0.0085(17) 0.0107(18) 0.0039(16) C30 0.029(2) 0.0222(19) 0.036(3) 0.0018(17) 0.018(2) 0.0061(17) C31 0.031(2) 0.0200(19) 0.031(3) -0.0025(17) 0.017(2) -0.0022(17) C32 0.0213(19) 0.0137(16) 0.023(2) 0.0008(14) 0.0131(17) -0.0013(14) N33 0.0233(19) 0.036(2) 0.028(2) 0.0105(17) 0.0117(17) 0.0065(17) O34 0.031(2) 0.039(2) 0.053(3) 0.0109(19) 0.016(2) 0.0118(17) O35 0.030(2) 0.045(2) 0.035(2) 0.0084(17) 0.0108(17) 0.0031(17) O36 0.0171(14) 0.0224(14) 0.0238(16) -0.0020(12) 0.0078(12) -0.0040(11) O100 0.031(2) 0.0296(19) 0.041(2) 0.0025(15) 0.0120(18) 0.0038(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 Cu O25 1.963(4) . ? Cu N1 2.003(4) . ? Cu N7 2.010(4) . ? Cu N4 2.070(4) . ? Cu N10 2.302(4) . ? Cu O36 2.343(3) . ? N1 C15 1.490(5) . ? N1 C14 1.499(5) . ? N1 C2 1.507(5) . ? C2 C3 1.534(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.484(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.471(6) . ? N4 C12 1.503(6) . ? C5 C6 1.531(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N7 1.501(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N7 C8 1.483(5) . ? N7 C26 1.503(6) . ? C8 C9 1.535(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N10 1.462(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N10 C13 1.462(6) . ? N10 C11 1.467(6) . ? C11 C12 1.530(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.554(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.509(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.383(6) . ? C16 C21 1.423(6) . ? C17 C18 1.397(6) . ? C17 H17 0.9500 . ? C18 C19 1.401(6) . ? C18 N22 1.422(5) . ? C19 C20 1.383(6) . ? C19 H19 0.9500 . ? C20 C21 1.441(6) . ? C20 H20 0.9500 . ? C21 O25 1.299(5) . ? N22 O24 1.232(5) . ? N22 O23 1.247(6) . ? C26 C27 1.490(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.390(6) . ? C27 C32 1.433(6) . ? C28 C29 1.405(7) . ? C28 H28 0.9500 . ? C29 C30 1.397(7) . ? C29 N33 1.417(6) . ? C30 C31 1.373(7) . ? C30 H30 0.9500 . ? C31 C32 1.431(6) . ? C31 H31 0.9500 . ? C32 O36 1.296(5) . ? N33 O35 1.234(6) . ? N33 O34 1.255(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O25 Cu N1 92.36(15) . . ? O25 Cu N7 93.31(15) . . ? N1 Cu N7 166.77(14) . . ? O25 Cu N4 177.91(17) . . ? N1 Cu N4 87.90(16) . . ? N7 Cu N4 86.00(16) . . ? O25 Cu N10 99.72(14) . . ? N1 Cu N10 81.55(14) . . ? N7 Cu N10 85.71(14) . . ? N4 Cu N10 78.26(14) . . ? O25 Cu O36 87.64(14) . . ? N1 Cu O36 104.53(13) . . ? N7 Cu O36 87.65(12) . . ? N4 Cu O36 94.30(13) . . ? N10 Cu O36 170.34(12) . . ? C15 N1 C14 111.9(3) . . ? C15 N1 C2 108.9(3) . . ? C14 N1 C2 113.8(3) . . ? C15 N1 Cu 108.0(3) . . ? C14 N1 Cu 108.5(3) . . ? C2 N1 Cu 105.3(3) . . ? N1 C2 C3 111.8(4) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C2 108.0(4) . . ? N4 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? N4 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C5 N4 C3 116.9(4) . . ? C5 N4 C12 110.2(4) . . ? C3 N4 C12 112.5(4) . . ? C5 N4 Cu 102.3(3) . . ? C3 N4 Cu 96.9(3) . . ? C12 N4 Cu 117.5(3) . . ? N4 C5 C6 108.0(4) . . ? N4 C5 H5A 110.1 . . ? C6 C5 H5A 110.1 . . ? N4 C5 H5B 110.1 . . ? C6 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N7 C6 C5 111.5(3) . . ? N7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 N7 C6 114.6(3) . . ? C8 N7 C26 109.3(3) . . ? C6 N7 C26 111.9(4) . . ? C8 N7 Cu 101.4(3) . . ? C6 N7 Cu 108.1(3) . . ? C26 N7 Cu 111.2(3) . . ? N7 C8 C9 115.4(4) . . ? N7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? N7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? N10 C9 C8 115.3(3) . . ? N10 C9 H9A 108.5 . . ? C8 C9 H9A 108.5 . . ? N10 C9 H9B 108.5 . . ? C8 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 N10 C13 119.2(4) . . ? C9 N10 C11 114.6(4) . . ? C13 N10 C11 113.8(4) . . ? C9 N10 Cu 101.4(3) . . ? C13 N10 Cu 94.3(2) . . ? C11 N10 Cu 110.3(3) . . ? N10 C11 C12 111.2(4) . . ? N10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? N10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N4 C12 C11 113.4(4) . . ? N4 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? N4 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N10 C13 C14 110.9(4) . . ? N10 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N10 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? N1 C14 C13 114.0(3) . . ? N1 C14 H14A 108.7 . . ? C13 C14 H14A 108.7 . . ? N1 C14 H14B 108.7 . . ? C13 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? N1 C15 C16 115.1(3) . . ? N1 C15 H15A 108.5 . . ? C16 C15 H15A 108.5 . . ? N1 C15 H15B 108.5 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C21 120.0(4) . . ? C17 C16 C15 117.4(4) . . ? C21 C16 C15 122.6(4) . . ? C16 C17 C18 120.9(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C19 120.6(4) . . ? C17 C18 N22 119.8(4) . . ? C19 C18 N22 119.5(4) . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.7(4) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? O25 C21 C16 124.6(4) . . ? O25 C21 C20 117.2(4) . . ? C16 C21 C20 118.2(4) . . ? O24 N22 O23 122.0(4) . . ? O24 N22 C18 119.4(4) . . ? O23 N22 C18 118.6(4) . . ? C21 O25 Cu 125.7(3) . . ? C27 C26 N7 115.0(4) . . ? C27 C26 H26A 108.5 . . ? N7 C26 H26A 108.5 . . ? C27 C26 H26B 108.5 . . ? N7 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C28 C27 C32 120.0(4) . . ? C28 C27 C26 119.3(4) . . ? C32 C27 C26 120.7(4) . . ? C27 C28 C29 120.0(4) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 121.1(4) . . ? C30 C29 N33 119.2(4) . . ? C28 C29 N33 119.7(4) . . ? C31 C30 C29 119.4(4) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 121.6(4) . . ? C30 C31 H31 119.2 . . ? C32 C31 H31 119.2 . . ? O36 C32 C31 121.1(4) . . ? O36 C32 C27 121.0(4) . . ? C31 C32 C27 117.8(4) . . ? O35 N33 O34 121.6(4) . . ? O35 N33 C29 119.5(4) . . ? O34 N33 C29 118.9(5) . . ? C32 O36 Cu 123.5(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.153 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.202