Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof Derek Woollins' _publ_contact_author_address ; School of Chemistry University of St Andrews St Andrews Fife KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-AND.AC.UK _publ_section_title ; New Pyridine Carboxamide Ligands and their Complexation to Copper(II). X-Ray Crystal Structures of Mono-, Di, Tri- and Tetranuclear Copper Complexes. ; loop_ _publ_author_name 'Derek Woollins' 'Pravat Bhattacharyya' 'J. A. Crayston' 'Sneh L. Jain' 'Heather L. Milton' ; A.M.Z.Slawin ; data_1 _database_code_depnum_ccdc_archive 'CCDC 227112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28 Cu3 N10 O8.C H Cl3.[H2 O]0.25' _chemical_formula_sum 'C39 H29.50 Cl3 Cu3 N10 O8.25' _chemical_formula_weight 1067.20 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7236(10) _cell_length_b 14.9250(11) _cell_length_c 22.1202(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.379(2) _cell_angle_gamma 90.00 _cell_volume 4165.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 141 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max .05 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2150 _exptl_absorpt_coefficient_mu 1.777 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.83591 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17896 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 23.30 _reflns_number_total 5950 _reflns_number_gt 3997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0413P)^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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00024(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5950 _refine_ls_number_parameters 573 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.27714(4) 0.79562(3) 0.16541(2) 0.01778(14) Uani 1 1 d . . . Cu2 Cu 0.66953(4) 0.63623(3) 0.12500(2) 0.01930(15) Uani 1 1 d . . . Cu3 Cu 0.47703(4) 0.71009(3) 0.16051(2) 0.01616(14) Uani 1 1 d . . . N1 N 0.1257(3) 0.8392(2) 0.12642(16) 0.0195(9) Uani 1 1 d . . . C2 C 0.1336(3) 0.8816(3) 0.07400(19) 0.0185(10) Uani 1 1 d . . . C3 C 0.0457(3) 0.8995(3) 0.0324(2) 0.0260(11) Uani 1 1 d . . . H3A H 0.0534 0.9292 -0.0048 0.031 Uiso 1 1 calc R . . C4 C -0.0531(4) 0.8740(3) 0.0452(2) 0.0297(12) Uani 1 1 d . . . H4A H -0.1143 0.8858 0.0169 0.036 Uiso 1 1 calc R . . C5 C -0.0620(3) 0.8311(3) 0.0996(2) 0.0267(12) Uani 1 1 d . . . H5A H -0.1293 0.8134 0.1097 0.032 Uiso 1 1 calc R . . C6 C 0.0294(3) 0.8146(3) 0.1390(2) 0.0239(11) Uani 1 1 d . . . H6A H 0.0237 0.7847 0.1764 0.029 Uiso 1 1 calc R . . C7 C 0.2422(3) 0.9096(3) 0.0612(2) 0.0198(11) Uani 1 1 d . . . O7 O 0.2507(2) 0.9630(2) 0.01986(14) 0.0326(8) Uani 1 1 d . . . N8 N 0.3214(3) 0.8691(2) 0.09934(15) 0.0186(8) Uani 1 1 d . . . C9 C 0.4274(3) 0.8902(3) 0.09605(18) 0.0174(10) Uani 1 1 d . . . N10 N 0.4978(3) 0.8274(2) 0.12110(15) 0.0166(8) Uani 1 1 d . . . C11 C 0.6029(3) 0.8383(3) 0.12114(19) 0.0182(10) Uani 1 1 d . . . C12 C 0.6434(3) 0.9133(3) 0.09429(19) 0.0213(11) Uani 1 1 d . . . H12A H 0.7172 0.9193 0.0923 0.026 Uiso 1 1 calc R . . C13 C 0.5732(3) 0.9781(3) 0.07092(18) 0.0179(10) Uani 1 1 d . . . H13A H 0.5990 1.0310 0.0540 0.021 Uiso 1 1 calc R . . C14 C 0.4656(3) 0.9675(3) 0.07167(18) 0.0184(10) Uani 1 1 d . . . H14A H 0.4178 1.0130 0.0555 0.022 Uiso 1 1 calc R . . N15 N 0.6645(3) 0.7691(2) 0.15001(15) 0.0164(8) Uani 1 1 d . . . C16 C 0.7284(3) 0.7910(3) 0.2016(2) 0.0220(10) Uani 1 1 d . . . O16 O 0.7435(3) 0.8656(2) 0.22486(14) 0.0348(8) Uani 1 1 d . . . C17 C 0.7812(3) 0.7108(3) 0.23315(19) 0.0203(10) Uani 1 1 d . . . N18 N 0.7602(3) 0.6313(2) 0.20496(15) 0.0199(8) Uani 1 1 d . . . C19 C 0.8045(3) 0.5574(3) 0.2306(2) 0.0264(11) Uani 1 1 d . . . H19A H 0.7870 0.5012 0.2117 0.032 Uiso 1 1 calc R . . C20 C 0.8747(3) 0.5591(3) 0.2834(2) 0.0287(12) Uani 1 1 d . . . H20A H 0.9078 0.5056 0.2995 0.034 Uiso 1 1 calc R . . C21 C 0.8960(3) 0.6406(3) 0.3126(2) 0.0302(12) Uani 1 1 d . . . H21A H 0.9426 0.6438 0.3497 0.036 Uiso 1 1 calc R . . C22 C 0.8485(3) 0.7169(3) 0.2869(2) 0.0270(11) Uani 1 1 d . . . H22A H 0.8621 0.7734 0.3062 0.032 Uiso 1 1 calc R . . N31 N 0.2269(2) 0.7240(2) 0.23171(15) 0.0161(8) Uani 1 1 d . . . C32 C 0.2129(3) 0.6359(3) 0.21920(19) 0.0208(10) Uani 1 1 d . . . C33 C 0.1826(3) 0.5772(3) 0.2620(2) 0.0239(11) Uani 1 1 d . . . H33A H 0.1730 0.5154 0.2525 0.029 Uiso 1 1 calc R . . C34 C 0.1664(4) 0.6090(3) 0.3187(2) 0.0299(12) Uani 1 1 d . . . H34A H 0.1476 0.5691 0.3490 0.036 Uiso 1 1 calc R . . C35 C 0.1780(3) 0.6998(3) 0.3309(2) 0.0258(11) Uani 1 1 d . . . H35A H 0.1647 0.7236 0.3690 0.031 Uiso 1 1 calc R . . C36 C 0.2092(3) 0.7545(3) 0.2865(2) 0.0213(11) Uani 1 1 d . . . H36A H 0.2185 0.8166 0.2950 0.026 Uiso 1 1 calc R . . C37 C 0.2344(3) 0.6054(3) 0.1574(2) 0.0218(11) Uani 1 1 d . . . O37 O 0.2104(3) 0.5285(2) 0.13997(14) 0.0343(8) Uani 1 1 d . . . N38 N 0.2823(3) 0.6694(2) 0.12761(15) 0.0174(8) Uani 1 1 d . . . C39 C 0.3226(3) 0.6459(3) 0.07365(19) 0.0196(10) Uani 1 1 d . . . N40 N 0.4293(3) 0.6571(2) 0.07819(15) 0.0183(9) Uani 1 1 d . . . C41 C 0.4825(3) 0.6377(3) 0.03084(18) 0.0183(10) Uani 1 1 d . . . C42 C 0.4270(3) 0.6057(3) -0.0239(2) 0.0257(11) Uani 1 1 d . . . H42A H 0.4636 0.5919 -0.0576 0.031 Uiso 1 1 calc R . . C43 C 0.3191(4) 0.5946(3) -0.0282(2) 0.0294(12) Uani 1 1 d . . . H43A H 0.2809 0.5730 -0.0650 0.035 Uiso 1 1 calc R . . C44 C 0.2660(3) 0.6145(3) 0.0207(2) 0.0276(12) Uani 1 1 d . . . H44A H 0.1914 0.6066 0.0178 0.033 Uiso 1 1 calc R . . N45 N 0.5924(3) 0.6454(2) 0.04247(15) 0.0205(8) Uani 1 1 d . . . C46 C 0.6522(3) 0.6525(3) -0.0040(2) 0.0235(11) Uani 1 1 d . . . O46 O 0.6212(2) 0.6704(2) -0.05796(14) 0.0332(8) Uani 1 1 d . . . C47 C 0.7686(3) 0.6371(3) 0.0149(2) 0.0240(11) Uani 1 1 d . . . N48 N 0.7980(3) 0.6189(2) 0.07384(16) 0.0220(9) Uani 1 1 d . . . C49 C 0.9003(3) 0.6001(3) 0.0916(2) 0.0287(12) Uani 1 1 d . . . H49A H 0.9220 0.5878 0.1335 0.034 Uiso 1 1 calc R . . C50 C 0.9747(4) 0.5977(4) 0.0524(2) 0.0393(14) Uani 1 1 d . . . H50A H 1.0462 0.5827 0.0667 0.047 Uiso 1 1 calc R . . C51 C 0.9441(4) 0.6174(4) -0.0085(2) 0.0489(16) Uani 1 1 d . . . H51A H 0.9944 0.6180 -0.0367 0.059 Uiso 1 1 calc R . . C52 C 0.8387(4) 0.6362(4) -0.0272(2) 0.0394(13) Uani 1 1 d . . . H52A H 0.8150 0.6484 -0.0688 0.047 Uiso 1 1 calc R . . O61 O 0.3692(2) 0.86726(18) 0.22893(12) 0.0204(7) Uani 1 1 d . . . C61 C 0.4522(3) 0.8350(3) 0.2577(2) 0.0198(10) Uani 1 1 d . . . C62 C 0.4992(4) 0.8817(3) 0.3152(2) 0.0328(12) Uani 1 1 d . . . H62A H 0.4555 0.9337 0.3225 0.049 Uiso 1 1 calc R . . H62B H 0.5712 0.9016 0.3109 0.049 Uiso 1 1 calc R . . H62C H 0.5014 0.8402 0.3497 0.049 Uiso 1 1 calc R . . O62 O 0.4997(2) 0.76600(18) 0.24212(12) 0.0200(7) Uani 1 1 d . . . O63 O 0.4842(2) 0.59490(18) 0.20130(12) 0.0214(7) Uani 1 1 d . . . C63 C 0.5248(4) 0.5246(3) 0.18140(19) 0.0219(11) Uani 1 1 d . . . C64 C 0.4849(4) 0.4363(3) 0.2032(2) 0.0309(12) Uani 1 1 d . . . H64A H 0.5212 0.3869 0.1854 0.046 Uiso 1 1 calc R . . H64B H 0.4084 0.4316 0.1906 0.046 Uiso 1 1 calc R . . H64C H 0.4993 0.4333 0.2478 0.046 Uiso 1 1 calc R . . O64 O 0.5940(2) 0.52291(18) 0.14566(12) 0.0205(7) Uani 1 1 d . . . C70 C 0.9257(4) 1.1417(4) 0.1499(2) 0.0443(14) Uani 1 1 d . . . H70A H 0.9304 1.1742 0.1896 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.84319(11) 1.20418(10) 0.09562(6) 0.0549(4) Uani 1 1 d . . . Cl2 Cl 0.87120(12) 1.03616(9) 0.15982(7) 0.0591(4) Uani 1 1 d . . . Cl3 Cl 1.05385(11) 1.13326(13) 0.12975(7) 0.0703(5) Uani 1 1 d . . . O80 O 0.5005(13) 0.8155(11) -0.0529(7) 0.071(5) Uiso 0.25 1 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 Cu1 0.0178(3) 0.0174(3) 0.0191(3) 0.0023(2) 0.0061(2) -0.0004(2) Cu2 0.0178(3) 0.0207(3) 0.0200(3) -0.0017(3) 0.0050(2) -0.0009(2) Cu3 0.0179(3) 0.0148(3) 0.0164(3) -0.0005(2) 0.0047(2) 0.0003(2) N1 0.017(2) 0.018(2) 0.023(2) 0.0018(17) 0.0020(17) 0.0008(16) C2 0.022(3) 0.013(2) 0.021(3) 0.003(2) 0.005(2) 0.006(2) C3 0.025(3) 0.030(3) 0.024(3) 0.003(2) 0.002(2) 0.001(2) C4 0.020(3) 0.034(3) 0.033(3) 0.003(2) -0.003(2) 0.007(2) C5 0.016(3) 0.024(3) 0.042(3) 0.006(2) 0.008(2) 0.001(2) C6 0.023(3) 0.019(3) 0.031(3) 0.003(2) 0.011(2) 0.003(2) C7 0.018(3) 0.017(2) 0.025(3) 0.000(2) 0.006(2) -0.003(2) O7 0.0239(18) 0.040(2) 0.034(2) 0.0207(17) 0.0032(15) -0.0019(16) N8 0.017(2) 0.0194(19) 0.020(2) 0.0030(17) 0.0038(16) -0.0016(17) C9 0.016(2) 0.021(3) 0.016(2) -0.0009(19) 0.0010(19) -0.001(2) N10 0.016(2) 0.018(2) 0.016(2) -0.0016(15) 0.0021(16) -0.0021(16) C11 0.023(3) 0.019(3) 0.013(2) -0.0034(19) 0.0031(19) -0.002(2) C12 0.018(3) 0.024(3) 0.023(3) -0.002(2) 0.003(2) -0.003(2) C13 0.020(3) 0.017(2) 0.016(2) 0.0007(19) 0.0016(19) -0.008(2) C14 0.022(3) 0.019(2) 0.015(2) 0.000(2) 0.0061(19) 0.000(2) N15 0.0128(19) 0.019(2) 0.018(2) 0.0022(16) 0.0032(16) 0.0005(16) C16 0.016(2) 0.024(3) 0.026(3) 0.003(2) 0.006(2) -0.002(2) O16 0.045(2) 0.0200(18) 0.035(2) -0.0066(16) -0.0103(16) -0.0003(17) C17 0.015(2) 0.023(2) 0.024(3) 0.000(2) 0.007(2) -0.002(2) N18 0.021(2) 0.019(2) 0.021(2) 0.0014(18) 0.0085(16) 0.0006(18) C19 0.027(3) 0.024(3) 0.029(3) 0.001(2) 0.005(2) 0.000(2) C20 0.028(3) 0.032(3) 0.026(3) 0.011(2) 0.005(2) 0.004(2) C21 0.023(3) 0.038(3) 0.028(3) 0.010(3) -0.005(2) -0.002(2) C22 0.025(3) 0.028(3) 0.027(3) -0.004(2) -0.002(2) -0.007(2) N31 0.0115(19) 0.017(2) 0.020(2) -0.0006(16) 0.0056(15) 0.0006(15) C32 0.016(2) 0.021(2) 0.025(3) -0.001(2) 0.0038(19) -0.001(2) C33 0.022(3) 0.020(3) 0.030(3) 0.003(2) 0.005(2) -0.004(2) C34 0.031(3) 0.033(3) 0.028(3) 0.008(2) 0.009(2) -0.003(2) C35 0.026(3) 0.031(3) 0.022(3) -0.002(2) 0.013(2) 0.001(2) C36 0.020(3) 0.019(2) 0.026(3) -0.001(2) 0.007(2) 0.003(2) C37 0.016(2) 0.023(3) 0.026(3) -0.003(2) 0.002(2) 0.001(2) O37 0.046(2) 0.0240(19) 0.035(2) -0.0072(16) 0.0138(16) -0.0113(16) N38 0.014(2) 0.020(2) 0.020(2) -0.0013(16) 0.0088(16) -0.0042(16) C39 0.021(3) 0.019(2) 0.020(3) 0.000(2) 0.008(2) -0.005(2) N40 0.022(2) 0.015(2) 0.018(2) -0.0022(16) 0.0051(17) -0.0024(16) C41 0.025(3) 0.013(2) 0.018(2) -0.001(2) 0.008(2) -0.001(2) C42 0.021(3) 0.037(3) 0.020(3) -0.009(2) 0.007(2) 0.000(2) C43 0.029(3) 0.041(3) 0.020(3) -0.012(2) 0.006(2) -0.007(2) C44 0.016(3) 0.039(3) 0.028(3) -0.002(2) 0.004(2) -0.008(2) N45 0.016(2) 0.025(2) 0.022(2) -0.0042(17) 0.0079(17) -0.0025(17) C46 0.021(3) 0.025(3) 0.026(3) -0.002(2) 0.008(2) -0.002(2) O46 0.0257(19) 0.054(2) 0.0202(19) 0.0045(16) 0.0049(15) -0.0062(16) C47 0.020(3) 0.029(3) 0.024(3) -0.004(2) 0.006(2) -0.001(2) N48 0.014(2) 0.028(2) 0.024(2) -0.0034(18) 0.0061(17) -0.0029(17) C49 0.022(3) 0.035(3) 0.029(3) 0.003(2) 0.005(2) 0.000(2) C50 0.021(3) 0.070(4) 0.029(3) -0.003(3) 0.008(2) 0.003(3) C51 0.025(3) 0.090(5) 0.035(3) 0.000(3) 0.018(3) 0.008(3) C52 0.023(3) 0.073(4) 0.024(3) 0.005(3) 0.007(2) 0.007(3) O61 0.0219(17) 0.0178(16) 0.0218(17) -0.0038(14) 0.0041(14) -0.0008(14) C61 0.022(3) 0.018(3) 0.021(3) 0.003(2) 0.009(2) -0.002(2) C62 0.038(3) 0.026(3) 0.032(3) -0.007(2) -0.004(2) 0.006(2) O62 0.0257(17) 0.0157(16) 0.0191(17) -0.0008(13) 0.0041(14) 0.0040(14) O63 0.0285(18) 0.0136(16) 0.0233(18) -0.0001(14) 0.0084(14) 0.0028(14) C63 0.026(3) 0.021(3) 0.017(3) 0.001(2) -0.004(2) -0.002(2) C64 0.035(3) 0.019(3) 0.042(3) 0.000(2) 0.016(2) -0.004(2) O64 0.0214(17) 0.0189(17) 0.0228(18) -0.0016(13) 0.0092(14) -0.0012(14) C70 0.038(3) 0.055(4) 0.042(3) -0.016(3) 0.012(3) -0.016(3) Cl1 0.0505(9) 0.0624(9) 0.0508(9) -0.0109(8) 0.0034(7) 0.0007(8) Cl2 0.0567(10) 0.0465(9) 0.0703(11) -0.0169(8) -0.0062(8) -0.0134(8) Cl3 0.0341(8) 0.1289(15) 0.0488(9) -0.0163(10) 0.0090(7) -0.0071(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N8 1.966(3) . ? Cu1 N31 1.985(3) . ? Cu1 O61 2.016(3) . ? Cu1 N38 2.065(3) . ? Cu1 N1 2.110(3) . ? Cu1 Cu3 2.8603(7) . ? Cu2 N45 1.963(3) . ? Cu2 N18 1.985(3) . ? Cu2 O64 2.026(3) . ? Cu2 N15 2.062(3) . ? Cu2 N48 2.120(3) . ? Cu2 Cu3 2.8854(7) . ? Cu3 O63 1.938(3) . ? Cu3 O62 1.976(3) . ? Cu3 N10 1.989(3) . ? Cu3 N40 2.007(3) . ? N1 C2 1.336(5) . ? N1 C6 1.343(5) . ? C2 C3 1.380(6) . ? C2 C7 1.505(6) . ? C3 C4 1.377(6) . ? C4 C5 1.380(6) . ? C5 C6 1.383(6) . ? C7 O7 1.229(5) . ? C7 N8 1.369(5) . ? N8 C9 1.396(5) . ? C9 N10 1.364(5) . ? C9 C14 1.388(6) . ? N10 C11 1.348(5) . ? C11 C12 1.396(6) . ? C11 N15 1.400(5) . ? C12 C13 1.372(5) . ? C13 C14 1.381(6) . ? N15 C16 1.354(5) . ? C16 O16 1.231(5) . ? C16 C17 1.501(6) . ? C17 N18 1.351(5) . ? C17 C22 1.376(6) . ? N18 C19 1.333(5) . ? C19 C20 1.376(6) . ? C20 C21 1.388(6) . ? C21 C22 1.376(6) . ? N31 C36 1.341(5) . ? N31 C32 1.351(5) . ? C32 C33 1.381(6) . ? C32 C37 1.498(6) . ? C33 C34 1.380(6) . ? C34 C35 1.386(6) . ? C35 C36 1.374(6) . ? C37 O37 1.237(5) . ? C37 N38 1.350(5) . ? N38 C39 1.403(5) . ? C39 N40 1.358(5) . ? C39 C44 1.377(6) . ? N40 C41 1.350(5) . ? C41 N45 1.394(5) . ? C41 C42 1.405(6) . ? C42 C43 1.374(6) . ? C43 C44 1.378(6) . ? N45 C46 1.359(5) . ? C46 O46 1.238(5) . ? C46 C47 1.505(6) . ? C47 N48 1.337(5) . ? C47 C52 1.369(6) . ? N48 C49 1.339(5) . ? C49 C50 1.363(6) . ? C50 C51 1.385(6) . ? C51 C52 1.381(6) . ? O61 C61 1.257(5) . ? C61 O62 1.265(5) . ? C61 C62 1.505(6) . ? O63 C63 1.273(5) . ? C63 O64 1.258(5) . ? C63 C64 1.513(6) . ? C70 Cl2 1.746(5) . ? C70 Cl3 1.749(5) . ? C70 Cl1 1.757(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Cu1 N31 177.69(14) . . ? N8 Cu1 O61 91.50(13) . . ? N31 Cu1 O61 89.08(12) . . ? N8 Cu1 N38 100.41(14) . . ? N31 Cu1 N38 80.68(14) . . ? O61 Cu1 N38 136.06(12) . . ? N8 Cu1 N1 81.82(14) . . ? N31 Cu1 N1 95.99(13) . . ? O61 Cu1 N1 122.64(12) . . ? N38 Cu1 N1 100.97(13) . . ? N8 Cu1 Cu3 83.11(10) . . ? N31 Cu1 Cu3 99.20(9) . . ? O61 Cu1 Cu3 79.83(8) . . ? N38 Cu1 Cu3 60.21(9) . . ? N1 Cu1 Cu3 153.10(10) . . ? N45 Cu2 N18 174.28(14) . . ? N45 Cu2 O64 94.21(13) . . ? N18 Cu2 O64 90.34(13) . . ? N45 Cu2 N15 98.81(14) . . ? N18 Cu2 N15 80.27(13) . . ? O64 Cu2 N15 135.25(12) . . ? N45 Cu2 N48 80.78(14) . . ? N18 Cu2 N48 94.10(14) . . ? O64 Cu2 N48 116.04(12) . . ? N15 Cu2 N48 108.26(13) . . ? N45 Cu2 Cu3 83.46(10) . . ? N18 Cu2 Cu3 100.83(10) . . ? O64 Cu2 Cu3 79.27(8) . . ? N15 Cu2 Cu3 60.18(9) . . ? N48 Cu2 Cu3 158.69(10) . . ? O63 Cu3 O62 87.52(11) . . ? O63 Cu3 N10 169.77(13) . . ? O62 Cu3 N10 90.95(12) . . ? O63 Cu3 N40 93.63(12) . . ? O62 Cu3 N40 170.82(13) . . ? N10 Cu3 N40 89.49(13) . . ? O63 Cu3 Cu1 111.54(9) . . ? O62 Cu3 Cu1 78.64(8) . . ? N10 Cu3 Cu1 78.01(10) . . ? N40 Cu3 Cu1 92.49(10) . . ? O63 Cu3 Cu2 78.29(9) . . ? O62 Cu3 Cu2 112.38(9) . . ? N10 Cu3 Cu2 92.98(10) . . ? N40 Cu3 Cu2 76.75(10) . . ? Cu1 Cu3 Cu2 166.14(2) . . ? C2 N1 C6 118.8(4) . . ? C2 N1 Cu1 109.6(3) . . ? C6 N1 Cu1 129.9(3) . . ? N1 C2 C3 121.8(4) . . ? N1 C2 C7 117.9(4) . . ? C3 C2 C7 120.4(4) . . ? C4 C3 C2 119.5(4) . . ? C3 C4 C5 119.1(4) . . ? C4 C5 C6 118.5(4) . . ? N1 C6 C5 122.4(4) . . ? O7 C7 N8 128.1(4) . . ? O7 C7 C2 119.4(4) . . ? N8 C7 C2 112.5(4) . . ? C7 N8 C9 120.5(3) . . ? C7 N8 Cu1 116.5(3) . . ? C9 N8 Cu1 122.4(3) . . ? N10 C9 C14 119.0(4) . . ? N10 C9 N8 114.3(4) . . ? C14 C9 N8 126.7(4) . . ? C11 N10 C9 121.1(3) . . ? C11 N10 Cu3 107.1(3) . . ? C9 N10 Cu3 131.8(3) . . ? N10 C11 C12 121.1(4) . . ? N10 C11 N15 114.1(4) . . ? C12 C11 N15 124.8(4) . . ? C13 C12 C11 117.9(4) . . ? C12 C13 C14 120.9(4) . . ? C13 C14 C9 119.8(4) . . ? C16 N15 C11 116.5(3) . . ? C16 N15 Cu2 115.0(3) . . ? C11 N15 Cu2 128.5(3) . . ? O16 C16 N15 128.0(4) . . ? O16 C16 C17 119.4(4) . . ? N15 C16 C17 112.5(4) . . ? N18 C17 C22 121.4(4) . . ? N18 C17 C16 115.8(4) . . ? C22 C17 C16 122.7(4) . . ? C19 N18 C17 118.8(4) . . ? C19 N18 Cu2 125.2(3) . . ? C17 N18 Cu2 115.9(3) . . ? N18 C19 C20 122.6(4) . . ? C19 C20 C21 118.5(4) . . ? C22 C21 C20 119.0(4) . . ? C21 C22 C17 119.5(4) . . ? C36 N31 C32 118.9(4) . . ? C36 N31 Cu1 126.3(3) . . ? C32 N31 Cu1 114.8(3) . . ? N31 C32 C33 121.2(4) . . ? N31 C32 C37 116.6(4) . . ? C33 C32 C37 122.1(4) . . ? C34 C33 C32 119.5(4) . . ? C33 C34 C35 119.2(4) . . ? C36 C35 C34 118.4(4) . . ? N31 C36 C35 122.8(4) . . ? O37 C37 N38 127.8(4) . . ? O37 C37 C32 120.0(4) . . ? N38 C37 C32 112.2(4) . . ? C37 N38 C39 118.4(3) . . ? C37 N38 Cu1 114.1(3) . . ? C39 N38 Cu1 127.3(3) . . ? N40 C39 C44 120.9(4) . . ? N40 C39 N38 112.2(4) . . ? C44 C39 N38 126.9(4) . . ? C41 N40 C39 120.8(4) . . ? C41 N40 Cu3 131.7(3) . . ? C39 N40 Cu3 107.4(3) . . ? N40 C41 N45 115.5(3) . . ? N40 C41 C42 119.7(4) . . ? N45 C41 C42 124.7(4) . . ? C43 C42 C41 119.2(4) . . ? C42 C43 C44 120.4(4) . . ? C39 C44 C43 119.0(4) . . ? C46 N45 C41 120.9(4) . . ? C46 N45 Cu2 116.5(3) . . ? C41 N45 Cu2 122.4(3) . . ? O46 C46 N45 127.3(4) . . ? O46 C46 C47 118.8(4) . . ? N45 C46 C47 113.9(4) . . ? N48 C47 C52 122.4(4) . . ? N48 C47 C46 116.3(4) . . ? C52 C47 C46 121.1(4) . . ? C47 N48 C49 117.9(4) . . ? C47 N48 Cu2 110.9(3) . . ? C49 N48 Cu2 131.0(3) . . ? N48 C49 C50 123.2(4) . . ? C49 C50 C51 118.7(5) . . ? C52 C51 C50 118.4(5) . . ? C47 C52 C51 119.4(5) . . ? C61 O61 Cu1 121.7(3) . . ? O61 C61 O62 125.0(4) . . ? O61 C61 C62 117.9(4) . . ? O62 C61 C62 117.1(4) . . ? C61 O62 Cu3 125.1(3) . . ? C63 O63 Cu3 124.6(3) . . ? O64 C63 O63 125.6(4) . . ? O64 C63 C64 118.3(4) . . ? O63 C63 C64 116.1(4) . . ? C63 O64 Cu2 121.1(3) . . ? Cl2 C70 Cl3 111.4(3) . . ? Cl2 C70 Cl1 110.6(3) . . ? Cl3 C70 Cl1 111.1(3) . . ? 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 N8 Cu1 Cu3 O63 -163.16(13) . . . . ? N31 Cu1 Cu3 O63 16.68(13) . . . . ? O61 Cu1 Cu3 O63 104.06(12) . . . . ? N38 Cu1 Cu3 O63 -56.96(14) . . . . ? N1 Cu1 Cu3 O63 -106.9(2) . . . . ? N8 Cu1 Cu3 O62 114.12(13) . . . . ? N31 Cu1 Cu3 O62 -66.05(13) . . . . ? O61 Cu1 Cu3 O62 21.34(11) . . . . ? N38 Cu1 Cu3 O62 -139.68(14) . . . . ? N1 Cu1 Cu3 O62 170.4(2) . . . . ? N8 Cu1 Cu3 N10 20.69(13) . . . . ? N31 Cu1 Cu3 N10 -159.48(13) . . . . ? O61 Cu1 Cu3 N10 -72.09(12) . . . . ? N38 Cu1 Cu3 N10 126.88(14) . . . . ? N1 Cu1 Cu3 N10 77.0(2) . . . . ? N8 Cu1 Cu3 N40 -68.27(14) . . . . ? N31 Cu1 Cu3 N40 111.57(14) . . . . ? O61 Cu1 Cu3 N40 -161.05(12) . . . . ? N38 Cu1 Cu3 N40 37.93(15) . . . . ? N1 Cu1 Cu3 N40 -12.0(2) . . . . ? N8 Cu1 Cu3 Cu2 -29.63(14) . . . . ? N31 Cu1 Cu3 Cu2 150.20(13) . . . . ? O61 Cu1 Cu3 Cu2 -122.41(13) . . . . ? N38 Cu1 Cu3 Cu2 76.56(15) . . . . ? N1 Cu1 Cu3 Cu2 26.6(2) . . . . ? N45 Cu2 Cu3 O63 118.20(13) . . . . ? N18 Cu2 Cu3 O63 -65.64(13) . . . . ? O64 Cu2 Cu3 O63 22.64(12) . . . . ? N15 Cu2 Cu3 O63 -137.71(13) . . . . ? N48 Cu2 Cu3 O63 160.7(3) . . . . ? N45 Cu2 Cu3 O62 -159.44(13) . . . . ? N18 Cu2 Cu3 O62 16.72(13) . . . . ? O64 Cu2 Cu3 O62 105.00(12) . . . . ? N15 Cu2 Cu3 O62 -55.35(13) . . . . ? N48 Cu2 Cu3 O62 -117.0(3) . . . . ? N45 Cu2 Cu3 N10 -67.19(14) . . . . ? N18 Cu2 Cu3 N10 108.97(14) . . . . ? O64 Cu2 Cu3 N10 -162.75(12) . . . . ? N15 Cu2 Cu3 N10 36.90(14) . . . . ? N48 Cu2 Cu3 N10 -24.7(3) . . . . ? N45 Cu2 Cu3 N40 21.59(14) . . . . ? N18 Cu2 Cu3 N40 -162.25(14) . . . . ? O64 Cu2 Cu3 N40 -73.97(12) . . . . ? N15 Cu2 Cu3 N40 125.68(14) . . . . ? N48 Cu2 Cu3 N40 64.1(3) . . . . ? N45 Cu2 Cu3 Cu1 -18.26(15) . . . . ? N18 Cu2 Cu3 Cu1 157.89(14) . . . . ? O64 Cu2 Cu3 Cu1 -113.83(12) . . . . ? N15 Cu2 Cu3 Cu1 85.83(14) . . . . ? N48 Cu2 Cu3 Cu1 24.2(3) . . . . ? N8 Cu1 N1 C2 8.6(3) . . . . ? N31 Cu1 N1 C2 -172.1(3) . . . . ? O61 Cu1 N1 C2 95.2(3) . . . . ? N38 Cu1 N1 C2 -90.5(3) . . . . ? Cu3 Cu1 N1 C2 -47.9(4) . . . . ? N8 Cu1 N1 C6 172.9(4) . . . . ? N31 Cu1 N1 C6 -7.8(4) . . . . ? O61 Cu1 N1 C6 -100.6(4) . . . . ? N38 Cu1 N1 C6 73.8(4) . . . . ? Cu3 Cu1 N1 C6 116.3(4) . . . . ? C6 N1 C2 C3 -0.9(6) . . . . ? Cu1 N1 C2 C3 165.3(3) . . . . ? C6 N1 C2 C7 179.2(4) . . . . ? Cu1 N1 C2 C7 -14.5(4) . . . . ? N1 C2 C3 C4 0.7(6) . . . . ? C7 C2 C3 C4 -179.5(4) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C3 C4 C5 C6 -0.7(7) . . . . ? C2 N1 C6 C5 0.3(6) . . . . ? Cu1 N1 C6 C5 -162.7(3) . . . . ? C4 C5 C6 N1 0.4(7) . . . . ? N1 C2 C7 O7 -166.2(4) . . . . ? C3 C2 C7 O7 14.0(6) . . . . ? N1 C2 C7 N8 14.2(5) . . . . ? C3 C2 C7 N8 -165.6(4) . . . . ? O7 C7 N8 C9 3.5(7) . . . . ? C2 C7 N8 C9 -177.0(4) . . . . ? O7 C7 N8 Cu1 174.5(4) . . . . ? C2 C7 N8 Cu1 -5.9(4) . . . . ? N31 Cu1 N8 C7 -19(4) . . . . ? O61 Cu1 N8 C7 -123.9(3) . . . . ? N38 Cu1 N8 C7 98.6(3) . . . . ? N1 Cu1 N8 C7 -1.1(3) . . . . ? Cu3 Cu1 N8 C7 156.5(3) . . . . ? N31 Cu1 N8 C9 151(3) . . . . ? O61 Cu1 N8 C9 47.0(3) . . . . ? N38 Cu1 N8 C9 -90.5(3) . . . . ? N1 Cu1 N8 C9 169.8(3) . . . . ? Cu3 Cu1 N8 C9 -32.6(3) . . . . ? C7 N8 C9 N10 -160.0(4) . . . . ? Cu1 N8 C9 N10 29.5(5) . . . . ? C7 N8 C9 C14 21.5(6) . . . . ? Cu1 N8 C9 C14 -149.0(3) . . . . ? C14 C9 N10 C11 -1.6(6) . . . . ? N8 C9 N10 C11 179.8(4) . . . . ? C14 C9 N10 Cu3 179.6(3) . . . . ? N8 C9 N10 Cu3 1.0(5) . . . . ? O63 Cu3 N10 C11 3.6(9) . . . . ? O62 Cu3 N10 C11 84.9(3) . . . . ? N40 Cu3 N10 C11 -104.3(3) . . . . ? Cu1 Cu3 N10 C11 163.1(3) . . . . ? Cu2 Cu3 N10 C11 -27.6(3) . . . . ? O63 Cu3 N10 C9 -177.5(6) . . . . ? O62 Cu3 N10 C9 -96.2(4) . . . . ? N40 Cu3 N10 C9 74.6(4) . . . . ? Cu1 Cu3 N10 C9 -18.1(3) . . . . ? Cu2 Cu3 N10 C9 151.3(3) . . . . ? C9 N10 C11 C12 -1.5(6) . . . . ? Cu3 N10 C11 C12 177.5(3) . . . . ? C9 N10 C11 N15 178.4(3) . . . . ? Cu3 N10 C11 N15 -2.6(4) . . . . ? N10 C11 C12 C13 3.7(6) . . . . ? N15 C11 C12 C13 -176.2(4) . . . . ? C11 C12 C13 C14 -2.7(6) . . . . ? C12 C13 C14 C9 -0.3(6) . . . . ? N10 C9 C14 C13 2.5(6) . . . . ? N8 C9 C14 C13 -179.0(4) . . . . ? N10 C11 N15 C16 -114.4(4) . . . . ? C12 C11 N15 C16 65.5(5) . . . . ? N10 C11 N15 Cu2 64.7(5) . . . . ? C12 C11 N15 Cu2 -115.4(4) . . . . ? N45 Cu2 N15 C16 -168.2(3) . . . . ? N18 Cu2 N15 C16 6.1(3) . . . . ? O64 Cu2 N15 C16 86.6(3) . . . . ? N48 Cu2 N15 C16 -85.0(3) . . . . ? Cu3 Cu2 N15 C16 114.6(3) . . . . ? N45 Cu2 N15 C11 12.7(4) . . . . ? N18 Cu2 N15 C11 -173.0(4) . . . . ? O64 Cu2 N15 C11 -92.4(4) . . . . ? N48 Cu2 N15 C11 95.9(3) . . . . ? Cu3 Cu2 N15 C11 -64.4(3) . . . . ? C11 N15 C16 O16 -4.0(7) . . . . ? Cu2 N15 C16 O16 176.8(4) . . . . ? C11 N15 C16 C17 173.2(4) . . . . ? Cu2 N15 C16 C17 -6.0(4) . . . . ? O16 C16 C17 N18 179.5(4) . . . . ? N15 C16 C17 N18 2.1(5) . . . . ? O16 C16 C17 C22 -1.6(7) . . . . ? N15 C16 C17 C22 -179.0(4) . . . . ? C22 C17 N18 C19 1.1(6) . . . . ? C16 C17 N18 C19 -180.0(4) . . . . ? C22 C17 N18 Cu2 -175.8(3) . . . . ? C16 C17 N18 Cu2 3.1(5) . . . . ? N45 Cu2 N18 C19 -100.3(15) . . . . ? O64 Cu2 N18 C19 42.4(3) . . . . ? N15 Cu2 N18 C19 178.4(4) . . . . ? N48 Cu2 N18 C19 -73.7(3) . . . . ? Cu3 Cu2 N18 C19 121.5(3) . . . . ? N45 Cu2 N18 C17 76.4(15) . . . . ? O64 Cu2 N18 C17 -140.9(3) . . . . ? N15 Cu2 N18 C17 -4.9(3) . . . . ? N48 Cu2 N18 C17 103.0(3) . . . . ? Cu3 Cu2 N18 C17 -61.7(3) . . . . ? C17 N18 C19 C20 -2.9(6) . . . . ? Cu2 N18 C19 C20 173.7(3) . . . . ? N18 C19 C20 C21 3.2(7) . . . . ? C19 C20 C21 C22 -1.7(7) . . . . ? C20 C21 C22 C17 0.0(7) . . . . ? N18 C17 C22 C21 0.3(6) . . . . ? C16 C17 C22 C21 -178.5(4) . . . . ? N8 Cu1 N31 C36 -68(4) . . . . ? O61 Cu1 N31 C36 36.2(3) . . . . ? N38 Cu1 N31 C36 173.3(3) . . . . ? N1 Cu1 N31 C36 -86.6(3) . . . . ? Cu3 Cu1 N31 C36 115.7(3) . . . . ? N8 Cu1 N31 C32 113(3) . . . . ? O61 Cu1 N31 C32 -142.0(3) . . . . ? N38 Cu1 N31 C32 -4.9(3) . . . . ? N1 Cu1 N31 C32 95.3(3) . . . . ? Cu3 Cu1 N31 C32 -62.4(3) . . . . ? C36 N31 C32 C33 -1.1(6) . . . . ? Cu1 N31 C32 C33 177.2(3) . . . . ? C36 N31 C32 C37 -179.7(3) . . . . ? Cu1 N31 C32 C37 -1.4(4) . . . . ? N31 C32 C33 C34 -0.1(6) . . . . ? C37 C32 C33 C34 178.4(4) . . . . ? C32 C33 C34 C35 1.8(6) . . . . ? C33 C34 C35 C36 -2.4(6) . . . . ? C32 N31 C36 C35 0.5(6) . . . . ? Cu1 N31 C36 C35 -177.6(3) . . . . ? C34 C35 C36 N31 1.2(6) . . . . ? N31 C32 C37 O37 -170.7(4) . . . . ? C33 C32 C37 O37 10.7(6) . . . . ? N31 C32 C37 N38 10.6(5) . . . . ? C33 C32 C37 N38 -167.9(4) . . . . ? O37 C37 N38 C39 -8.6(7) . . . . ? C32 C37 N38 C39 169.9(3) . . . . ? O37 C37 N38 Cu1 167.2(4) . . . . ? C32 C37 N38 Cu1 -14.3(4) . . . . ? N8 Cu1 N38 C37 -166.8(3) . . . . ? N31 Cu1 N38 C37 11.1(3) . . . . ? O61 Cu1 N38 C37 89.9(3) . . . . ? N1 Cu1 N38 C37 -83.3(3) . . . . ? Cu3 Cu1 N38 C37 117.4(3) . . . . ? N8 Cu1 N38 C39 8.5(4) . . . . ? N31 Cu1 N38 C39 -173.5(3) . . . . ? O61 Cu1 N38 C39 -94.7(4) . . . . ? N1 Cu1 N38 C39 92.1(3) . . . . ? Cu3 Cu1 N38 C39 -67.3(3) . . . . ? C37 N38 C39 N40 -117.8(4) . . . . ? Cu1 N38 C39 N40 67.0(4) . . . . ? C37 N38 C39 C44 61.9(6) . . . . ? Cu1 N38 C39 C44 -113.3(4) . . . . ? C44 C39 N40 C41 0.1(6) . . . . ? N38 C39 N40 C41 179.8(3) . . . . ? C44 C39 N40 Cu3 176.9(3) . . . . ? N38 C39 N40 Cu3 -3.4(4) . . . . ? O63 Cu3 N40 C41 -100.1(4) . . . . ? O62 Cu3 N40 C41 163.0(6) . . . . ? N10 Cu3 N40 C41 70.1(4) . . . . ? Cu1 Cu3 N40 C41 148.1(4) . . . . ? Cu2 Cu3 N40 C41 -23.0(3) . . . . ? O63 Cu3 N40 C39 83.6(3) . . . . ? O62 Cu3 N40 C39 -13.3(9) . . . . ? N10 Cu3 N40 C39 -106.2(3) . . . . ? Cu1 Cu3 N40 C39 -28.2(3) . . . . ? Cu2 Cu3 N40 C39 160.7(3) . . . . ? C39 N40 C41 N45 -175.4(4) . . . . ? Cu3 N40 C41 N45 8.7(6) . . . . ? C39 N40 C41 C42 0.1(6) . . . . ? Cu3 N40 C41 C42 -175.8(3) . . . . ? N40 C41 C42 C43 -0.1(6) . . . . ? N45 C41 C42 C43 174.9(4) . . . . ? C41 C42 C43 C44 -0.1(7) . . . . ? N40 C39 C44 C43 -0.3(7) . . . . ? N38 C39 C44 C43 -180.0(4) . . . . ? C42 C43 C44 C39 0.3(7) . . . . ? N40 C41 N45 C46 -161.5(4) . . . . ? C42 C41 N45 C46 23.3(6) . . . . ? N40 C41 N45 Cu2 24.0(5) . . . . ? C42 C41 N45 Cu2 -151.3(3) . . . . ? N18 Cu2 N45 C46 16.1(16) . . . . ? O64 Cu2 N45 C46 -126.5(3) . . . . ? N15 Cu2 N45 C46 96.5(3) . . . . ? N48 Cu2 N45 C46 -10.8(3) . . . . ? Cu3 Cu2 N45 C46 154.8(3) . . . . ? N18 Cu2 N45 C41 -169.1(13) . . . . ? O64 Cu2 N45 C41 48.3(3) . . . . ? N15 Cu2 N45 C41 -88.8(3) . . . . ? N48 Cu2 N45 C41 164.0(3) . . . . ? Cu3 Cu2 N45 C41 -30.4(3) . . . . ? C41 N45 C46 O46 15.2(7) . . . . ? Cu2 N45 C46 O46 -170.0(4) . . . . ? C41 N45 C46 C47 -165.4(4) . . . . ? Cu2 N45 C46 C47 9.4(5) . . . . ? O46 C46 C47 N48 179.3(4) . . . . ? N45 C46 C47 N48 -0.1(6) . . . . ? O46 C46 C47 C52 -4.7(7) . . . . ? N45 C46 C47 C52 175.8(4) . . . . ? C52 C47 N48 C49 0.6(7) . . . . ? C46 C47 N48 C49 176.5(4) . . . . ? C52 C47 N48 Cu2 175.9(4) . . . . ? C46 C47 N48 Cu2 -8.2(5) . . . . ? N45 Cu2 N48 C47 10.2(3) . . . . ? N18 Cu2 N48 C47 -167.2(3) . . . . ? O64 Cu2 N48 C47 100.4(3) . . . . ? N15 Cu2 N48 C47 -86.1(3) . . . . ? Cu3 Cu2 N48 C47 -32.6(5) . . . . ? N45 Cu2 N48 C49 -175.3(4) . . . . ? N18 Cu2 N48 C49 7.3(4) . . . . ? O64 Cu2 N48 C49 -85.1(4) . . . . ? N15 Cu2 N48 C49 88.4(4) . . . . ? Cu3 Cu2 N48 C49 141.9(3) . . . . ? C47 N48 C49 C50 -0.7(7) . . . . ? Cu2 N48 C49 C50 -175.0(4) . . . . ? N48 C49 C50 C51 1.4(8) . . . . ? C49 C50 C51 C52 -1.8(8) . . . . ? N48 C47 C52 C51 -1.1(8) . . . . ? C46 C47 C52 C51 -176.8(5) . . . . ? C50 C51 C52 C47 1.7(8) . . . . ? N8 Cu1 O61 C61 -108.8(3) . . . . ? N31 Cu1 O61 C61 73.4(3) . . . . ? N38 Cu1 O61 C61 -2.1(4) . . . . ? N1 Cu1 O61 C61 169.9(3) . . . . ? Cu3 Cu1 O61 C61 -26.1(3) . . . . ? Cu1 O61 C61 O62 16.6(6) . . . . ? Cu1 O61 C61 C62 -163.4(3) . . . . ? O61 C61 O62 Cu3 15.7(6) . . . . ? C62 C61 O62 Cu3 -164.2(3) . . . . ? O63 Cu3 O62 C61 -138.8(3) . . . . ? N10 Cu3 O62 C61 51.3(3) . . . . ? N40 Cu3 O62 C61 -41.4(9) . . . . ? Cu1 Cu3 O62 C61 -26.3(3) . . . . ? Cu2 Cu3 O62 C61 144.9(3) . . . . ? O62 Cu3 O63 C63 -144.6(3) . . . . ? N10 Cu3 O63 C63 -63.0(8) . . . . ? N40 Cu3 O63 C63 44.5(3) . . . . ? Cu1 Cu3 O63 C63 138.6(3) . . . . ? Cu2 Cu3 O63 C63 -31.1(3) . . . . ? Cu3 O63 C63 O64 24.3(6) . . . . ? Cu3 O63 C63 C64 -155.6(3) . . . . ? O63 C63 O64 Cu2 10.2(6) . . . . ? C64 C63 O64 Cu2 -169.9(3) . . . . ? N45 Cu2 O64 C63 -106.2(3) . . . . ? N18 Cu2 O64 C63 77.3(3) . . . . ? N15 Cu2 O64 C63 0.8(4) . . . . ? N48 Cu2 O64 C63 172.0(3) . . . . ? Cu3 Cu2 O64 C63 -23.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.418 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.074 data_2 _database_code_depnum_ccdc_archive 'CCDC 227113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H24 Cu3 N14 O.[ C2 H3 N]1.5.[H2 O]0.50' _chemical_formula_sum 'C37 H29.50 Cu3 N15.50 O8.50' _chemical_formula_weight 1017.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9969(14) _cell_length_b 18.980(3) _cell_length_c 20.125(3) _cell_angle_alpha 101.014(2) _cell_angle_beta 101.375(2) _cell_angle_gamma 99.055(2) _cell_volume 3958.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 89 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description plate _exptl_crystal_colour 'red brown' _exptl_crystal_size_max .14 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2060 _exptl_absorpt_coefficient_mu 1.674 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.799568 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20088 _diffrn_reflns_av_R_equivalents 0.1455 _diffrn_reflns_av_sigmaI/netI 0.1812 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 23.46 _reflns_number_total 11343 _reflns_number_gt 6403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0216P)^2^+61.0561P] 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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00037(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11343 _refine_ls_number_parameters 549 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1831 _refine_ls_R_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.2044 _refine_ls_wR_factor_gt 0.1685 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.44130(15) 0.11159(9) 0.31688(8) 0.0198(4) Uani 1 1 d . . . Cu2 Cu 0.34681(13) 0.17365(8) 0.03756(8) 0.0147(4) Uani 1 1 d . . . Cu3 Cu 0.34548(13) 0.14111(8) 0.17479(8) 0.0150(4) Uani 1 1 d . . . N1 N 0.5906(10) 0.0749(6) 0.3760(6) 0.024(3) Uiso 1 1 d . . . C2 C 0.7003(12) 0.1041(7) 0.3616(7) 0.021(3) Uiso 1 1 d . . . C3 C 0.8098(13) 0.0770(8) 0.3847(7) 0.028(3) Uiso 1 1 d . . . H3A H 0.8874 0.0975 0.3752 0.033 Uiso 1 1 calc R . . N4 N 0.8079(11) 0.0226(7) 0.4201(6) 0.036(3) Uiso 1 1 d . . . C5 C 0.6974(14) -0.0039(8) 0.4314(8) 0.036(4) Uiso 1 1 d . . . H5A H 0.6917 -0.0432 0.4543 0.043 Uiso 1 1 calc R . . C6 C 0.5878(14) 0.0235(8) 0.4108(7) 0.031(4) Uiso 1 1 d . . . H6A H 0.5114 0.0046 0.4224 0.038 Uiso 1 1 calc R . . C7 C 0.7023(12) 0.1629(7) 0.3241(7) 0.019(3) Uiso 1 1 d . . . O7 O 0.8049(8) 0.1925(5) 0.3152(5) 0.028(2) Uiso 1 1 d . . . N8 N 0.5856(9) 0.1776(6) 0.3019(5) 0.018(2) Uiso 1 1 d . . . C9 C 0.5782(11) 0.2369(6) 0.2728(6) 0.013(3) Uiso 1 1 d . . . N10 N 0.4834(9) 0.2271(5) 0.2160(5) 0.014(2) Uiso 1 1 d . . . C11 C 0.4661(12) 0.2828(7) 0.1824(7) 0.019(3) Uiso 1 1 d . . . C12 C 0.5446(11) 0.3515(7) 0.2077(6) 0.017(3) Uiso 1 1 d . . . H12A H 0.5330 0.3904 0.1851 0.021 Uiso 1 1 calc R . . C13 C 0.6415(12) 0.3619(7) 0.2677(7) 0.022(3) Uiso 1 1 d . . . H13A H 0.6966 0.4085 0.2858 0.026 Uiso 1 1 calc R . . C14 C 0.6580(13) 0.3068(7) 0.3002(7) 0.025(3) Uiso 1 1 d . . . H14A H 0.7229 0.3151 0.3414 0.030 Uiso 1 1 calc R . . N15 N 0.3673(9) 0.2615(5) 0.1231(5) 0.013(2) Uiso 1 1 d . . . C16 C 0.2890(12) 0.3060(7) 0.1122(7) 0.019(3) Uiso 1 1 d . . . O16 O 0.2884(9) 0.3670(5) 0.1472(5) 0.033(2) Uiso 1 1 d . . . C17 C 0.1772(11) 0.2713(7) 0.0500(6) 0.017(3) Uiso 1 1 d . . . N18 N 0.1868(9) 0.2100(6) 0.0076(5) 0.019(3) Uiso 1 1 d . . . C19 C 0.0915(12) 0.1777(7) -0.0470(7) 0.021(3) Uiso 1 1 d . . . H19A H 0.0970 0.1344 -0.0780 0.025 Uiso 1 1 calc R . . C20 C -0.0159(12) 0.2074(7) -0.0585(7) 0.021(3) Uiso 1 1 d . . . H20A H -0.0831 0.1829 -0.0975 0.025 Uiso 1 1 calc R . . N21 N -0.0303(11) 0.2677(6) -0.0185(6) 0.031(3) Uiso 1 1 d . . . C22 C 0.0700(12) 0.3003(7) 0.0368(7) 0.024(3) Uiso 1 1 d . . . H22A H 0.0656 0.3444 0.0670 0.028 Uiso 1 1 calc R . . O23 O 0.3440(8) 0.1896(5) 0.3350(5) 0.023(2) Uiso 1 1 d . . . O24 O 0.2303(8) 0.1807(5) 0.2269(5) 0.025(2) Uiso 1 1 d . . . C23 C 0.2492(12) 0.1979(7) 0.2942(7) 0.024(3) Uiso 1 1 d . . . C24 C 0.1501(13) 0.2285(8) 0.3220(8) 0.032(4) Uiso 1 1 d . . . H24A H 0.1730 0.2386 0.3730 0.048 Uiso 1 1 calc R . . H24B H 0.0693 0.1932 0.3045 0.048 Uiso 1 1 calc R . . H24C H 0.1417 0.2742 0.3072 0.048 Uiso 1 1 calc R . . N31 N 0.2976(10) 0.0428(6) 0.3360(6) 0.023(3) Uiso 1 1 d . . . C32 C 0.2484(12) -0.0192(7) 0.2864(7) 0.025(3) Uiso 1 1 d . . . C33 C 0.1426(12) -0.0674(7) 0.2904(7) 0.023(3) Uiso 1 1 d . . . H33A H 0.1094 -0.1103 0.2541 0.028 Uiso 1 1 calc R . . N34 N 0.0871(11) -0.0564(7) 0.3418(7) 0.038(3) Uiso 1 1 d . . . C35 C 0.1326(13) 0.0050(8) 0.3922(8) 0.034(4) Uiso 1 1 d . . . H35A H 0.0932 0.0140 0.4301 0.040 Uiso 1 1 calc R . . C36 C 0.2380(13) 0.0560(8) 0.3895(8) 0.031(4) Uiso 1 1 d . . . H36A H 0.2680 0.0998 0.4249 0.037 Uiso 1 1 calc R . . C37 C 0.3107(12) -0.0308(7) 0.2262(7) 0.022(3) Uiso 1 1 d . . . O37 O 0.2776(8) -0.0910(5) 0.1826(5) 0.028(2) Uiso 1 1 d . . . N38 N 0.3953(10) 0.0275(6) 0.2255(5) 0.021(3) Uiso 1 1 d . . . C39 C 0.4637(11) 0.0242(7) 0.1738(6) 0.016(3) Uiso 1 1 d . . . N40 N 0.4605(9) 0.0792(5) 0.1412(5) 0.017(2) Uiso 1 1 d . . . C41 C 0.5271(11) 0.0858(6) 0.0916(6) 0.013(3) Uiso 1 1 d . . . C42 C 0.6019(11) 0.0334(6) 0.0761(6) 0.014(3) Uiso 1 1 d . . . H42A H 0.6509 0.0379 0.0426 0.016 Uiso 1 1 calc R . . C43 C 0.6045(12) -0.0233(7) 0.1085(7) 0.019(3) Uiso 1 1 d . . . H43A H 0.6535 -0.0588 0.0971 0.023 Uiso 1 1 calc R . . C44 C 0.5339(12) -0.0286(7) 0.1589(7) 0.024(3) Uiso 1 1 d . . . H44A H 0.5344 -0.0675 0.1823 0.029 Uiso 1 1 calc R . . N45 N 0.5113(9) 0.1414(5) 0.0586(5) 0.013(2) Uiso 1 1 d . . . C46 C 0.5988(12) 0.1684(7) 0.0257(7) 0.019(3) Uiso 1 1 d . . . O46 O 0.7090(8) 0.1580(5) 0.0339(5) 0.028(2) Uiso 1 1 d . . . C47 C 0.5501(11) 0.2081(7) -0.0271(6) 0.016(3) Uiso 1 1 d . . . N48 N 0.4304(9) 0.2137(5) -0.0374(5) 0.016(2) Uiso 1 1 d . . . C49 C 0.3877(13) 0.2462(7) -0.0867(7) 0.022(3) Uiso 1 1 d . . . H49A H 0.3019 0.2516 -0.0947 0.026 Uiso 1 1 calc R . . C50 C 0.4643(12) 0.2730(7) -0.1278(7) 0.024(3) Uiso 1 1 d . . . H50A H 0.4287 0.2953 -0.1634 0.029 Uiso 1 1 calc R . . N51 N 0.5837(10) 0.2683(6) -0.1187(6) 0.028(3) Uiso 1 1 d . . . C52 C 0.6281(13) 0.2366(7) -0.0675(7) 0.022(3) Uiso 1 1 d . . . H52A H 0.7149 0.2333 -0.0581 0.027 Uiso 1 1 calc R . . O53 O 0.2455(7) 0.0696(4) 0.0105(4) 0.016(2) Uiso 1 1 d . . . O54 O 0.1961(8) 0.0723(4) 0.1141(4) 0.019(2) Uiso 1 1 d . . . C53 C 0.1920(11) 0.0422(7) 0.0517(7) 0.017(3) Uiso 1 1 d . . . C54 C 0.1221(12) -0.0380(7) 0.0280(7) 0.025(3) Uiso 1 1 d . . . H54A H 0.1231 -0.0569 -0.0207 0.037 Uiso 1 1 calc R . . H54B H 0.0343 -0.0414 0.0323 0.037 Uiso 1 1 calc R . . H54C H 0.1642 -0.0671 0.0571 0.037 Uiso 1 1 calc R . . Cu4 Cu 0.05882(14) 0.65303(9) 0.30299(8) 0.0166(4) Uani 1 1 d . . . Cu5 Cu -0.43420(14) 0.61439(8) 0.34773(8) 0.0157(4) Uani 1 1 d . . . Cu6 Cu -0.19980(13) 0.61305(8) 0.31365(8) 0.0143(4) Uani 1 1 d . . . N61 N 0.2249(9) 0.7335(5) 0.3072(5) 0.016(2) Uiso 1 1 d . . . C62 C 0.2401(12) 0.7896(7) 0.3609(7) 0.020(3) Uiso 1 1 d . . . C63 C 0.3341(12) 0.8512(7) 0.3725(7) 0.023(3) Uiso 1 1 d . . . H63A H 0.3430 0.8901 0.4118 0.027 Uiso 1 1 calc R . . N64 N 0.4123(10) 0.8577(6) 0.3308(6) 0.026(3) Uiso 1 1 d . . . C65 C 0.3939(12) 0.8028(7) 0.2761(7) 0.025(3) Uiso 1 1 d . . . H65A H 0.4468 0.8061 0.2443 0.030 Uiso 1 1 calc R . . C66 C 0.3019(12) 0.7417(8) 0.2636(7) 0.026(3) Uiso 1 1 d . . . H66A H 0.2918 0.7039 0.2233 0.031 Uiso 1 1 calc R . . C67 C 0.1515(11) 0.7843(7) 0.4091(6) 0.015(3) Uiso 1 1 d . . . O67 O 0.1685(8) 0.8359(5) 0.4594(5) 0.026(2) Uiso 1 1 d . . . N68 N 0.0663(9) 0.7202(6) 0.3917(5) 0.019(3) Uiso 1 1 d . . . C69 C 0.0003(11) 0.7015(7) 0.4400(6) 0.017(3) Uiso 1 1 d . . . N70 N -0.1147(9) 0.6560(5) 0.4136(5) 0.012(2) Uiso 1 1 d . . . C71 C -0.1835(10) 0.6334(6) 0.4567(6) 0.010(3) Uiso 1 1 d . . . C72 C -0.1390(11) 0.6522(6) 0.5278(6) 0.016(3) Uiso 1 1 d . . . H72A H -0.1884 0.6350 0.5574 0.019 Uiso 1 1 calc R . . C73 C -0.0217(11) 0.6963(7) 0.5548(7) 0.017(3) Uiso 1 1 d . . . H73A H 0.0118 0.7094 0.6038 0.020 Uiso 1 1 calc R . . C74 C 0.0479(11) 0.7219(7) 0.5118(6) 0.015(3) Uiso 1 1 d . . . H74A H 0.1285 0.7534 0.5310 0.018 Uiso 1 1 calc R . . N75 N -0.3025(9) 0.5891(5) 0.4210(5) 0.013(2) Uiso 1 1 d . . . C76 C -0.3437(12) 0.5287(7) 0.4437(7) 0.019(3) Uiso 1 1 d . . . O76 O -0.2933(9) 0.5045(5) 0.4915(5) 0.033(2) Uiso 1 1 d . . . C77 C -0.4692(11) 0.4834(7) 0.3945(6) 0.014(3) Uiso 1 1 d . . . N78 N -0.5133(9) 0.5095(5) 0.3384(5) 0.014(2) Uiso 1 1 d . . . C79 C -0.6140(11) 0.4672(7) 0.2923(7) 0.017(3) Uiso 1 1 d . . . H79A H -0.6453 0.4813 0.2504 0.020 Uiso 1 1 calc R . . C80 C -0.6741(13) 0.4027(7) 0.3046(7) 0.026(3) Uiso 1 1 d . . . H80A H -0.7474 0.3746 0.2710 0.032 Uiso 1 1 calc R . . N81 N -0.6355(11) 0.3786(6) 0.3597(6) 0.030(3) Uiso 1 1 d . . . C82 C -0.5297(12) 0.4192(7) 0.4050(7) 0.027(3) Uiso 1 1 d . . . H82A H -0.4963 0.4029 0.4453 0.032 Uiso 1 1 calc R . . O83 O 0.0714(8) 0.5681(5) 0.3469(4) 0.019(2) Uiso 1 1 d . . . O84 O -0.1407(8) 0.5225(5) 0.3198(4) 0.022(2) Uiso 1 1 d . . . C83 C -0.0233(12) 0.5196(7) 0.3448(7) 0.019(3) Uiso 1 1 d . . . C84 C -0.0031(15) 0.4572(9) 0.3784(9) 0.044(4) Uiso 1 1 d . . . H84A H 0.0878 0.4608 0.3960 0.066 Uiso 1 1 calc R . . H84B H -0.0385 0.4107 0.3440 0.066 Uiso 1 1 calc R . . H84C H -0.0454 0.4592 0.4170 0.066 Uiso 1 1 calc R . . N91 N 0.0678(9) 0.5931(5) 0.2126(5) 0.016(2) Uiso 1 1 d . . . C92 C 0.0011(11) 0.6081(6) 0.1549(6) 0.013(3) Uiso 1 1 d . . . C93 C 0.0120(12) 0.5772(7) 0.0902(7) 0.024(3) Uiso 1 1 d . . . H93A H -0.0335 0.5911 0.0511 0.029 Uiso 1 1 calc R . . N94 N 0.0876(11) 0.5260(7) 0.0796(6) 0.036(3) Uiso 1 1 d . . . C95 C 0.1489(13) 0.5115(8) 0.1370(7) 0.026(3) Uiso 1 1 d . . . H95A H 0.2032 0.4774 0.1330 0.031 Uiso 1 1 calc R . . C96 C 0.1382(12) 0.5427(7) 0.2018(7) 0.021(3) Uiso 1 1 d . . . H96A H 0.1824 0.5281 0.2407 0.026 Uiso 1 1 calc R . . C97 C -0.0831(12) 0.6615(7) 0.1683(7) 0.020(3) Uiso 1 1 d . . . O97 O -0.1488(9) 0.6792(5) 0.1175(5) 0.032(2) Uiso 1 1 d . . . N98 N -0.0771(9) 0.6850(5) 0.2369(5) 0.012(2) Uiso 1 1 d . . . C99 C -0.1527(12) 0.7340(7) 0.2577(7) 0.019(3) Uiso 1 1 d . . . N100 N -0.2239(9) 0.7121(5) 0.3001(5) 0.015(2) Uiso 1 1 d . . . C101 C -0.2933(12) 0.7547(7) 0.3312(7) 0.019(3) Uiso 1 1 d . . . C102 C -0.2895(12) 0.8244(7) 0.3188(7) 0.018(3) Uiso 1 1 d . . . H10A H -0.3362 0.8561 0.3406 0.022 Uiso 1 1 calc R . . C103 C -0.2188(11) 0.8478(7) 0.2753(6) 0.017(3) Uiso 1 1 d . . . H10B H -0.2178 0.8953 0.2665 0.020 Uiso 1 1 calc R . . C104 C -0.1480(11) 0.8020(7) 0.2437(7) 0.018(3) Uiso 1 1 d . . . H10C H -0.0983 0.8177 0.2135 0.021 Uiso 1 1 calc R . . N105 N -0.3683(9) 0.7219(5) 0.3698(5) 0.013(2) Uiso 1 1 d . . . C106 C -0.4015(11) 0.7613(7) 0.4220(6) 0.015(3) Uiso 1 1 d . . . O106 O -0.3567(8) 0.8275(5) 0.4513(5) 0.027(2) Uiso 1 1 d . . . C107 C -0.5034(12) 0.7212(7) 0.4476(7) 0.021(3) Uiso 1 1 d . . . N108 N -0.5578(9) 0.6532(5) 0.4128(5) 0.011(2) Uiso 1 1 d . . . C109 C -0.6573(11) 0.6182(7) 0.4322(7) 0.018(3) Uiso 1 1 d . . . H10D H -0.6977 0.5694 0.4081 0.021 Uiso 1 1 calc R . . C110 C -0.6999(12) 0.6534(7) 0.4867(7) 0.021(3) Uiso 1 1 d . . . H11D H -0.7711 0.6278 0.4985 0.025 Uiso 1 1 calc R . . N111 N -0.6473(10) 0.7214(6) 0.5241(6) 0.026(3) Uiso 1 1 d . . . C112 C -0.5486(12) 0.7546(8) 0.5032(7) 0.023(3) Uiso 1 1 d . . . H11E H -0.5076 0.8031 0.5276 0.028 Uiso 1 1 calc R . . O113 O -0.4922(7) 0.6036(4) 0.2457(4) 0.016(2) Uiso 1 1 d . . . O114 O -0.3210(8) 0.5611(4) 0.2254(4) 0.019(2) Uiso 1 1 d . . . C113 C -0.4336(12) 0.5731(7) 0.2056(7) 0.022(3) Uiso 1 1 d . . . C114 C -0.5001(13) 0.5430(8) 0.1303(7) 0.028(3) Uiso 1 1 d . . . H11A H -0.5837 0.5559 0.1218 0.042 Uiso 1 1 calc R . . H11B H -0.5101 0.4895 0.1192 0.042 Uiso 1 1 calc R . . H11C H -0.4499 0.5638 0.1009 0.042 Uiso 1 1 calc R . . N201 N -0.0831(12) -0.0395(7) 0.1791(7) 0.042(3) Uiso 1 1 d . . . C202 C -0.0816(13) 0.0198(8) 0.1788(7) 0.027(3) Uiso 1 1 d . . . C203 C -0.0779(15) 0.0957(8) 0.1782(8) 0.040(4) Uiso 1 1 d . . . H20B H 0.0079 0.1193 0.1779 0.061 Uiso 1 1 calc R . . H20C H -0.1017 0.1203 0.2197 0.061 Uiso 1 1 calc R . . H20D H -0.1375 0.0994 0.1364 0.061 Uiso 1 1 calc R . . N204 N 0.0096(18) 0.3835(11) 0.2092(10) 0.087(6) Uiso 1 1 d . . . C205 C -0.072(2) 0.3322(14) 0.1940(12) 0.082(7) Uiso 1 1 d . . . C206 C -0.165(2) 0.2657(12) 0.1759(12) 0.090(7) Uiso 1 1 d . . . H20E H -0.2302 0.2716 0.2026 0.134 Uiso 1 1 calc R . . H20F H -0.1251 0.2254 0.1867 0.134 Uiso 1 1 calc R . . H20G H -0.2052 0.2546 0.1260 0.134 Uiso 1 1 calc R . . N207 N 0.5403(17) 0.3831(9) 0.0365(9) 0.076(5) Uiso 1 1 d . . . C208 C 0.647(2) 0.4013(11) 0.0458(10) 0.062(5) Uiso 1 1 d . . . C209 C 0.778(3) 0.4179(17) 0.0562(17) 0.156(13) Uiso 1 1 d . . . H20H H 0.8173 0.4318 0.1063 0.234 Uiso 1 1 calc R . . H20I H 0.8027 0.4587 0.0350 0.234 Uiso 1 1 calc R . . H20J H 0.8078 0.3749 0.0348 0.234 Uiso 1 1 calc R . . O201 O -0.0763(17) 0.8691(10) 0.5020(10) 0.030(5) Uiso 0.50 1 d P . . O202 O -0.2920(17) 0.5744(10) 0.0020(10) 0.032(5) Uiso 0.50 1 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 Cu1 0.0186(9) 0.0202(10) 0.0175(9) 0.0039(7) 0.0022(7) -0.0019(7) Cu2 0.0089(8) 0.0180(9) 0.0148(9) 0.0017(7) -0.0008(6) 0.0032(7) Cu3 0.0107(8) 0.0155(9) 0.0155(9) -0.0002(7) 0.0003(7) 0.0010(7) Cu4 0.0141(8) 0.0202(9) 0.0134(9) 0.0013(7) 0.0007(7) 0.0037(7) Cu5 0.0120(8) 0.0176(9) 0.0149(9) 0.0026(7) 0.0002(7) 0.0006(7) Cu6 0.0110(8) 0.0156(9) 0.0130(9) 0.0013(7) -0.0020(6) 0.0012(7) _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 N8 1.972(10) . ? Cu1 O23 1.978(9) . ? Cu1 N31 2.032(11) . ? Cu1 N38 2.107(11) . ? Cu1 N1 2.122(11) . ? Cu1 Cu3 3.035(2) . ? Cu2 N45 1.993(9) . ? Cu2 N18 2.015(10) . ? Cu2 O53 2.024(8) . ? Cu2 N15 2.103(10) . ? Cu2 N48 2.112(10) . ? Cu2 Cu3 2.945(2) . ? Cu3 O24 1.947(9) . ? Cu3 O54 1.954(8) . ? Cu3 N10 1.965(10) . ? Cu3 N40 1.984(10) . ? N1 C6 1.305(17) . ? N1 C2 1.356(16) . ? C2 C3 1.412(18) . ? C2 C7 1.461(18) . ? C3 N4 1.362(17) . ? N4 C5 1.319(18) . ? C5 C6 1.406(19) . ? C7 O7 1.241(14) . ? C7 N8 1.364(15) . ? N8 C9 1.371(15) . ? C9 N10 1.348(15) . ? C9 C14 1.414(17) . ? N10 C11 1.377(16) . ? C11 C12 1.387(17) . ? C11 N15 1.391(15) . ? C12 C13 1.403(17) . ? C13 C14 1.352(18) . ? N15 C16 1.316(15) . ? C16 O16 1.235(15) . ? C16 C17 1.528(17) . ? C17 N18 1.336(15) . ? C17 C22 1.378(17) . ? N18 C19 1.330(16) . ? C19 C20 1.384(17) . ? C20 N21 1.318(16) . ? N21 C22 1.370(17) . ? O23 C23 1.246(15) . ? O24 C23 1.298(15) . ? C23 C24 1.468(18) . ? N31 C32 1.346(16) . ? N31 C36 1.371(17) . ? C32 C33 1.388(18) . ? C32 C37 1.504(19) . ? C33 N34 1.301(17) . ? N34 C35 1.343(18) . ? C35 C36 1.406(19) . ? C37 O37 1.252(15) . ? C37 N38 1.333(16) . ? N38 C39 1.397(16) . ? C39 N40 1.338(15) . ? C39 C44 1.381(17) . ? N40 C41 1.362(15) . ? C41 N45 1.365(15) . ? C41 C42 1.415(16) . ? C42 C43 1.363(17) . ? C43 C44 1.402(18) . ? N45 C46 1.360(15) . ? C46 O46 1.242(14) . ? C46 C47 1.480(17) . ? C47 N48 1.316(15) . ? C47 C52 1.410(17) . ? N48 C49 1.315(16) . ? C49 C50 1.399(18) . ? C50 N51 1.309(16) . ? N51 C52 1.339(16) . ? O53 C53 1.251(14) . ? O54 C53 1.265(14) . ? C53 C54 1.533(17) . ? Cu4 N68 1.965(10) . ? Cu4 N91 1.982(10) . ? Cu4 O83 1.991(8) . ? Cu4 N98 2.046(10) . ? Cu4 N61 2.165(10) . ? Cu4 Cu6 2.887(2) . ? Cu5 O113 1.987(8) . ? Cu5 N105 1.986(10) . ? Cu5 N78 2.000(10) . ? Cu5 N75 2.037(10) . ? Cu5 N108 2.181(9) . ? Cu5 Cu6 2.798(2) . ? Cu6 O84 1.948(8) . ? Cu6 O114 1.971(8) . ? Cu6 N70 1.994(10) . ? Cu6 N100 2.000(10) . ? N61 C62 1.328(15) . ? N61 C66 1.346(16) . ? C62 C63 1.381(17) . ? C62 C67 1.510(17) . ? C63 N64 1.323(16) . ? N64 C65 1.322(16) . ? C65 C66 1.360(18) . ? C67 O67 1.228(14) . ? C67 N68 1.353(15) . ? N68 C69 1.387(16) . ? C69 N70 1.357(15) . ? C69 C74 1.392(17) . ? N70 C71 1.344(15) . ? C71 C72 1.375(16) . ? C71 N75 1.410(14) . ? C72 C73 1.368(17) . ? C73 C74 1.369(17) . ? N75 C76 1.359(16) . ? C76 O76 1.217(15) . ? C76 C77 1.544(17) . ? C77 N78 1.352(15) . ? C77 C82 1.368(17) . ? N78 C79 1.327(15) . ? C79 C80 1.387(17) . ? C80 N81 1.299(17) . ? N81 C82 1.345(17) . ? O83 C83 1.265(14) . ? O84 C83 1.303(14) . ? C83 C84 1.496(19) . ? N91 C96 1.335(15) . ? N91 C92 1.350(15) . ? C92 C93 1.357(17) . ? C92 C97 1.500(17) . ? C93 N94 1.390(17) . ? N94 C95 1.319(17) . ? C95 C96 1.360(18) . ? C97 O97 1.263(15) . ? C97 N98 1.352(15) . ? N98 C99 1.401(15) . ? C99 N100 1.346(16) . ? C99 C104 1.369(17) . ? N100 C101 1.349(15) . ? C101 C102 1.388(17) . ? C101 N105 1.396(16) . ? C102 C103 1.371(17) . ? C103 C104 1.402(17) . ? N105 C106 1.317(15) . ? C106 O106 1.256(14) . ? C106 C107 1.486(17) . ? C107 N108 1.327(15) . ? C107 C112 1.396(18) . ? N108 C109 1.351(15) . ? C109 C110 1.375(17) . ? C110 N111 1.339(16) . ? N111 C112 1.349(16) . ? O113 C113 1.243(14) . ? O114 C113 1.294(14) . ? C113 C114 1.503(18) . ? N201 C202 1.124(17) . ? C202 C203 1.438(19) . ? N204 C205 1.16(2) . ? C205 C206 1.43(3) . ? N207 C208 1.14(2) . ? C208 C209 1.39(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 N8 Cu1 O23 94.3(4) . . ? N8 Cu1 N31 177.5(4) . . ? O23 Cu1 N31 86.8(4) . . ? N8 Cu1 N38 101.9(4) . . ? O23 Cu1 N38 124.5(4) . . ? N31 Cu1 N38 79.2(4) . . ? N8 Cu1 N1 81.4(4) . . ? O23 Cu1 N1 135.7(4) . . ? N31 Cu1 N1 96.2(4) . . ? N38 Cu1 N1 99.3(4) . . ? N8 Cu1 Cu3 75.4(3) . . ? O23 Cu1 Cu3 75.6(3) . . ? N31 Cu1 Cu3 107.0(3) . . ? N38 Cu1 Cu3 58.6(3) . . ? N1 Cu1 Cu3 142.6(3) . . ? N45 Cu2 N18 173.7(4) . . ? N45 Cu2 O53 92.8(4) . . ? N18 Cu2 O53 89.7(4) . . ? N45 Cu2 N15 102.5(4) . . ? N18 Cu2 N15 79.9(4) . . ? O53 Cu2 N15 132.8(4) . . ? N45 Cu2 N48 81.0(4) . . ? N18 Cu2 N48 92.7(4) . . ? O53 Cu2 N48 118.0(4) . . ? N15 Cu2 N48 108.4(4) . . ? N45 Cu2 Cu3 79.4(3) . . ? N18 Cu2 Cu3 106.8(3) . . ? O53 Cu2 Cu3 78.4(2) . . ? N15 Cu2 Cu3 61.5(3) . . ? N48 Cu2 Cu3 155.0(3) . . ? O24 Cu3 O54 86.6(4) . . ? O24 Cu3 N10 93.5(4) . . ? O54 Cu3 N10 163.4(4) . . ? O24 Cu3 N40 162.1(4) . . ? O54 Cu3 N40 91.8(4) . . ? N10 Cu3 N40 93.1(4) . . ? O24 Cu3 Cu2 118.6(3) . . ? O54 Cu3 Cu2 77.3(3) . . ? N10 Cu3 Cu2 88.2(3) . . ? N40 Cu3 Cu2 78.2(3) . . ? O24 Cu3 Cu1 78.3(3) . . ? O54 Cu3 Cu1 116.6(3) . . ? N10 Cu3 Cu1 79.5(3) . . ? N40 Cu3 Cu1 86.6(3) . . ? Cu2 Cu3 Cu1 159.95(7) . . ? C6 N1 C2 120.2(12) . . ? C6 N1 Cu1 130.8(10) . . ? C2 N1 Cu1 107.9(8) . . ? N1 C2 C3 118.2(12) . . ? N1 C2 C7 119.4(11) . . ? C3 C2 C7 122.3(12) . . ? N4 C3 C2 122.2(13) . . ? C5 N4 C3 116.2(13) . . ? N4 C5 C6 122.8(15) . . ? N1 C6 C5 120.3(14) . . ? O7 C7 N8 127.7(12) . . ? O7 C7 C2 118.9(11) . . ? N8 C7 C2 113.4(11) . . ? C7 N8 C9 118.2(10) . . ? C7 N8 Cu1 116.1(8) . . ? C9 N8 Cu1 125.7(8) . . ? N10 C9 N8 116.2(10) . . ? N10 C9 C14 119.2(11) . . ? N8 C9 C14 124.6(11) . . ? C9 N10 C11 121.4(10) . . ? C9 N10 Cu3 127.8(8) . . ? C11 N10 Cu3 110.6(8) . . ? N10 C11 C12 120.3(11) . . ? N10 C11 N15 113.1(11) . . ? C12 C11 N15 126.5(12) . . ? C11 C12 C13 118.0(12) . . ? C14 C13 C12 121.2(13) . . ? C13 C14 C9 119.8(13) . . ? C16 N15 C11 118.4(10) . . ? C16 N15 Cu2 114.1(8) . . ? C11 N15 Cu2 126.5(8) . . ? O16 C16 N15 129.8(12) . . ? O16 C16 C17 117.8(11) . . ? N15 C16 C17 112.1(11) . . ? N18 C17 C22 120.1(12) . . ? N18 C17 C16 117.0(10) . . ? C22 C17 C16 122.9(11) . . ? C19 N18 C17 119.0(11) . . ? C19 N18 Cu2 126.5(9) . . ? C17 N18 Cu2 114.4(8) . . ? N18 C19 C20 119.6(12) . . ? N21 C20 C19 123.9(12) . . ? C20 N21 C22 115.1(12) . . ? N21 C22 C17 122.2(12) . . ? C23 O23 Cu1 125.8(9) . . ? C23 O24 Cu3 125.8(8) . . ? O23 C23 O24 124.1(12) . . ? O23 C23 C24 119.6(13) . . ? O24 C23 C24 116.2(12) . . ? C32 N31 C36 117.0(12) . . ? C32 N31 Cu1 115.4(9) . . ? C36 N31 Cu1 127.3(9) . . ? N31 C32 C33 120.8(12) . . ? N31 C32 C37 116.3(12) . . ? C33 C32 C37 122.8(12) . . ? N34 C33 C32 122.7(13) . . ? C33 N34 C35 118.5(13) . . ? N34 C35 C36 120.7(14) . . ? N31 C36 C35 120.3(13) . . ? O37 C37 N38 127.6(12) . . ? O37 C37 C32 118.8(12) . . ? N38 C37 C32 113.6(11) . . ? C37 N38 C39 120.1(11) . . ? C37 N38 Cu1 114.6(8) . . ? C39 N38 Cu1 124.0(8) . . ? N40 C39 C44 121.9(12) . . ? N40 C39 N38 113.8(10) . . ? C44 C39 N38 124.1(12) . . ? C39 N40 C41 121.2(10) . . ? C39 N40 Cu3 109.7(8) . . ? C41 N40 Cu3 129.1(8) . . ? N40 C41 N45 116.5(10) . . ? N40 C41 C42 118.3(11) . . ? N45 C41 C42 125.2(11) . . ? C43 C42 C41 120.9(11) . . ? C42 C43 C44 119.2(12) . . ? C39 C44 C43 118.5(12) . . ? C46 N45 C41 121.5(10) . . ? C46 N45 Cu2 114.6(8) . . ? C41 N45 Cu2 122.7(8) . . ? O46 C46 N45 125.1(12) . . ? O46 C46 C47 120.2(11) . . ? N45 C46 C47 114.5(10) . . ? N48 C47 C52 120.6(11) . . ? N48 C47 C46 118.2(11) . . ? C52 C47 C46 121.1(11) . . ? C49 N48 C47 117.3(11) . . ? C49 N48 Cu2 132.1(9) . . ? C47 N48 Cu2 110.4(8) . . ? N48 C49 C50 122.1(12) . . ? N51 C50 C49 121.9(13) . . ? C50 N51 C52 116.0(12) . . ? N51 C52 C47 122.1(12) . . ? C53 O53 Cu2 121.7(8) . . ? C53 O54 Cu3 122.6(8) . . ? O53 C53 O54 126.8(12) . . ? O53 C53 C54 118.2(11) . . ? O54 C53 C54 114.8(11) . . ? N68 Cu4 N91 173.6(4) . . ? N68 Cu4 O83 93.0(4) . . ? N91 Cu4 O83 90.7(4) . . ? N68 Cu4 N98 101.0(4) . . ? N91 Cu4 N98 79.8(4) . . ? O83 Cu4 N98 136.8(4) . . ? N68 Cu4 N61 80.9(4) . . ? N91 Cu4 N61 92.7(4) . . ? O83 Cu4 N61 121.6(4) . . ? N98 Cu4 N61 101.0(4) . . ? N68 Cu4 Cu6 80.2(3) . . ? N91 Cu4 Cu6 105.7(3) . . ? O83 Cu4 Cu6 80.0(2) . . ? N98 Cu4 Cu6 62.8(3) . . ? N61 Cu4 Cu6 151.9(3) . . ? O113 Cu5 N105 95.8(4) . . ? O113 Cu5 N78 90.6(4) . . ? N105 Cu5 N78 170.9(4) . . ? O113 Cu5 N75 142.6(4) . . ? N105 Cu5 N75 97.9(4) . . ? N78 Cu5 N75 80.8(4) . . ? O113 Cu5 N108 117.3(3) . . ? N105 Cu5 N108 79.2(4) . . ? N78 Cu5 N108 92.0(4) . . ? N75 Cu5 N108 99.4(4) . . ? O113 Cu5 Cu6 82.0(2) . . ? N105 Cu5 Cu6 81.4(3) . . ? N78 Cu5 Cu6 106.0(3) . . ? N75 Cu5 Cu6 65.9(3) . . ? N108 Cu5 Cu6 153.8(3) . . ? O84 Cu6 O114 89.2(3) . . ? O84 Cu6 N70 90.2(4) . . ? O114 Cu6 N70 164.9(4) . . ? O84 Cu6 N100 166.8(4) . . ? O114 Cu6 N100 93.5(4) . . ? N70 Cu6 N100 90.4(4) . . ? O84 Cu6 Cu5 113.1(3) . . ? O114 Cu6 Cu5 77.3(2) . . ? N70 Cu6 Cu5 89.0(3) . . ? N100 Cu6 Cu5 80.1(3) . . ? O84 Cu6 Cu4 78.9(3) . . ? O114 Cu6 Cu4 114.9(2) . . ? N70 Cu6 Cu4 79.7(3) . . ? N100 Cu6 Cu4 88.2(3) . . ? Cu5 Cu6 Cu4 163.77(7) . . ? C62 N61 C66 116.3(11) . . ? C62 N61 Cu4 109.3(8) . . ? C66 N61 Cu4 133.8(9) . . ? N61 C62 C63 121.1(12) . . ? N61 C62 C67 118.1(11) . . ? C63 C62 C67 120.8(11) . . ? N64 C63 C62 122.1(13) . . ? C65 N64 C63 116.4(12) . . ? N64 C65 C66 122.4(13) . . ? N61 C66 C65 121.5(13) . . ? O67 C67 N68 128.8(12) . . ? O67 C67 C62 117.3(11) . . ? N68 C67 C62 113.8(11) . . ? C67 N68 C69 119.1(11) . . ? C67 N68 Cu4 117.1(8) . . ? C69 N68 Cu4 123.3(8) . . ? N70 C69 C74 119.3(11) . . ? N70 C69 N68 116.1(11) . . ? C74 C69 N68 124.5(11) . . ? C71 N70 C69 120.1(10) . . ? C71 N70 Cu6 112.3(8) . . ? C69 N70 Cu6 127.6(8) . . ? N70 C71 C72 122.1(11) . . ? N70 C71 N75 112.9(10) . . ? C72 C71 N75 125.0(11) . . ? C73 C72 C71 118.2(12) . . ? C72 C73 C74 120.5(12) . . ? C73 C74 C69 119.8(12) . . ? C76 N75 C71 118.1(10) . . ? C76 N75 Cu5 114.8(8) . . ? C71 N75 Cu5 126.4(8) . . ? O76 C76 N75 130.2(12) . . ? O76 C76 C77 118.8(12) . . ? N75 C76 C77 110.7(11) . . ? N78 C77 C82 121.6(11) . . ? N78 C77 C76 115.9(11) . . ? C82 C77 C76 122.4(12) . . ? C79 N78 C77 116.1(11) . . ? C79 N78 Cu5 129.8(9) . . ? C77 N78 Cu5 113.0(8) . . ? N78 C79 C80 120.9(12) . . ? N81 C80 C79 123.4(13) . . ? C80 N81 C82 116.2(13) . . ? N81 C82 C77 121.6(13) . . ? C83 O83 Cu4 123.3(8) . . ? C83 O84 Cu6 124.0(8) . . ? O83 C83 O84 124.6(12) . . ? O83 C83 C84 119.0(12) . . ? O84 C83 C84 116.2(12) . . ? C96 N91 C92 115.9(11) . . ? C96 N91 Cu4 127.6(9) . . ? C92 N91 Cu4 116.4(8) . . ? N91 C92 C93 121.8(11) . . ? N91 C92 C97 114.8(10) . . ? C93 C92 C97 123.4(11) . . ? C92 C93 N94 121.9(13) . . ? C95 N94 C93 114.5(12) . . ? N94 C95 C96 123.4(13) . . ? N91 C96 C95 122.4(13) . . ? O97 C97 N98 128.0(12) . . ? O97 C97 C92 119.5(11) . . ? N98 C97 C92 112.5(11) . . ? C97 N98 C99 119.3(10) . . ? C97 N98 Cu4 115.4(8) . . ? C99 N98 Cu4 124.9(8) . . ? N100 C99 C104 120.7(11) . . ? N100 C99 N98 114.0(11) . . ? C104 C99 N98 124.9(11) . . ? C99 N100 C101 123.0(11) . . ? C99 N100 Cu6 110.0(8) . . ? C101 N100 Cu6 127.0(8) . . ? N100 C101 C102 117.8(11) . . ? N100 C101 N105 115.6(11) . . ? C102 C101 N105 126.5(11) . . ? C103 C102 C101 120.4(12) . . ? C102 C103 C104 120.3(12) . . ? C99 C104 C103 117.8(12) . . ? C106 N105 C101 121.2(11) . . ? C106 N105 Cu5 116.5(8) . . ? C101 N105 Cu5 122.2(8) . . ? O106 C106 N105 127.1(12) . . ? O106 C106 C107 118.3(11) . . ? N105 C106 C107 114.6(11) . . ? N108 C107 C112 119.8(12) . . ? N108 C107 C106 118.0(11) . . ? C112 C107 C106 122.0(12) . . ? C107 N108 C109 118.6(11) . . ? C107 N108 Cu5 107.5(8) . . ? C109 N108 Cu5 132.5(8) . . ? N108 C109 C110 119.9(12) . . ? N111 C110 C109 124.0(12) . . ? C110 N111 C112 114.4(12) . . ? N111 C112 C107 123.4(13) . . ? C113 O113 Cu5 119.8(8) . . ? C113 O114 Cu6 124.7(8) . . ? O113 C113 O114 124.1(12) . . ? O113 C113 C114 118.6(11) . . ? O114 C113 C114 117.2(11) . . ? N201 C202 C203 179.2(17) . . ? N204 C205 C206 176(3) . . ? N207 C208 C209 176(3) . . ? 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 N45 Cu2 Cu3 O24 162.6(4) . . . . ? N18 Cu2 Cu3 O24 -16.1(4) . . . . ? O53 Cu2 Cu3 O24 -102.3(4) . . . . ? N15 Cu2 Cu3 O24 52.0(4) . . . . ? N48 Cu2 Cu3 O24 123.8(7) . . . . ? N45 Cu2 Cu3 O54 -118.5(4) . . . . ? N18 Cu2 Cu3 O54 62.8(4) . . . . ? O53 Cu2 Cu3 O54 -23.4(3) . . . . ? N15 Cu2 Cu3 O54 130.9(4) . . . . ? N48 Cu2 Cu3 O54 -157.3(7) . . . . ? N45 Cu2 Cu3 N10 69.6(4) . . . . ? N18 Cu2 Cu3 N10 -109.1(4) . . . . ? O53 Cu2 Cu3 N10 164.7(4) . . . . ? N15 Cu2 Cu3 N10 -41.0(4) . . . . ? N48 Cu2 Cu3 N10 30.8(7) . . . . ? N45 Cu2 Cu3 N40 -23.9(4) . . . . ? N18 Cu2 Cu3 N40 157.3(4) . . . . ? O53 Cu2 Cu3 N40 71.2(4) . . . . ? N15 Cu2 Cu3 N40 -134.5(4) . . . . ? N48 Cu2 Cu3 N40 -62.7(7) . . . . ? N45 Cu2 Cu3 Cu1 17.6(4) . . . . ? N18 Cu2 Cu3 Cu1 -161.2(4) . . . . ? O53 Cu2 Cu3 Cu1 112.7(3) . . . . ? N15 Cu2 Cu3 Cu1 -93.0(3) . . . . ? N48 Cu2 Cu3 Cu1 -21.2(7) . . . . ? N8 Cu1 Cu3 O24 -118.5(4) . . . . ? O23 Cu1 Cu3 O24 -20.1(4) . . . . ? N31 Cu1 Cu3 O24 61.9(4) . . . . ? N38 Cu1 Cu3 O24 127.3(4) . . . . ? N1 Cu1 Cu3 O24 -172.0(6) . . . . ? N8 Cu1 Cu3 O54 161.4(4) . . . . ? O23 Cu1 Cu3 O54 -100.2(4) . . . . ? N31 Cu1 Cu3 O54 -18.2(4) . . . . ? N38 Cu1 Cu3 O54 47.2(4) . . . . ? N1 Cu1 Cu3 O54 107.9(6) . . . . ? N8 Cu1 Cu3 N10 -22.7(4) . . . . ? O23 Cu1 Cu3 N10 75.7(4) . . . . ? N31 Cu1 Cu3 N10 157.8(4) . . . . ? N38 Cu1 Cu3 N10 -136.8(4) . . . . ? N1 Cu1 Cu3 N10 -76.2(6) . . . . ? N8 Cu1 Cu3 N40 71.1(4) . . . . ? O23 Cu1 Cu3 N40 169.6(4) . . . . ? N31 Cu1 Cu3 N40 -108.4(4) . . . . ? N38 Cu1 Cu3 N40 -43.0(4) . . . . ? N1 Cu1 Cu3 N40 17.6(6) . . . . ? N8 Cu1 Cu3 Cu2 30.6(4) . . . . ? O23 Cu1 Cu3 Cu2 129.0(3) . . . . ? N31 Cu1 Cu3 Cu2 -149.0(4) . . . . ? N38 Cu1 Cu3 Cu2 -83.6(4) . . . . ? N1 Cu1 Cu3 Cu2 -22.9(6) . . . . ? N8 Cu1 N1 C6 -179.1(13) . . . . ? O23 Cu1 N1 C6 93.6(13) . . . . ? N31 Cu1 N1 C6 1.7(13) . . . . ? N38 Cu1 N1 C6 -78.3(13) . . . . ? Cu3 Cu1 N1 C6 -127.2(11) . . . . ? N8 Cu1 N1 C2 -11.7(9) . . . . ? O23 Cu1 N1 C2 -99.0(9) . . . . ? N31 Cu1 N1 C2 169.2(9) . . . . ? N38 Cu1 N1 C2 89.1(9) . . . . ? Cu3 Cu1 N1 C2 40.2(11) . . . . ? C6 N1 C2 C3 0(2) . . . . ? Cu1 N1 C2 C3 -168.5(10) . . . . ? C6 N1 C2 C7 -178.4(12) . . . . ? Cu1 N1 C2 C7 12.6(15) . . . . ? N1 C2 C3 N4 1(2) . . . . ? C7 C2 C3 N4 179.4(13) . . . . ? C2 C3 N4 C5 0(2) . . . . ? C3 N4 C5 C6 -2(2) . . . . ? C2 N1 C6 C5 -2(2) . . . . ? Cu1 N1 C6 C5 163.7(10) . . . . ? N4 C5 C6 N1 4(2) . . . . ? N1 C2 C7 O7 175.3(11) . . . . ? C3 C2 C7 O7 -4(2) . . . . ? N1 C2 C7 N8 -5.6(18) . . . . ? C3 C2 C7 N8 175.6(12) . . . . ? O7 C7 N8 C9 -8(2) . . . . ? C2 C7 N8 C9 173.2(11) . . . . ? O7 C7 N8 Cu1 173.4(11) . . . . ? C2 C7 N8 Cu1 -5.6(14) . . . . ? O23 Cu1 N8 C7 145.3(9) . . . . ? N31 Cu1 N8 C7 30(11) . . . . ? N38 Cu1 N8 C7 -88.1(9) . . . . ? N1 Cu1 N8 C7 9.6(9) . . . . ? Cu3 Cu1 N8 C7 -140.8(9) . . . . ? O23 Cu1 N8 C9 -33.4(10) . . . . ? N31 Cu1 N8 C9 -149(10) . . . . ? N38 Cu1 N8 C9 93.2(10) . . . . ? N1 Cu1 N8 C9 -169.0(10) . . . . ? Cu3 Cu1 N8 C9 40.5(9) . . . . ? C7 N8 C9 N10 138.4(11) . . . . ? Cu1 N8 C9 N10 -43.0(15) . . . . ? C7 N8 C9 C14 -45.0(17) . . . . ? Cu1 N8 C9 C14 133.6(11) . . . . ? N8 C9 N10 C11 179.7(10) . . . . ? C14 C9 N10 C11 2.9(17) . . . . ? N8 C9 N10 Cu3 6.0(15) . . . . ? C14 C9 N10 Cu3 -170.8(9) . . . . ? O24 Cu3 N10 C9 92.9(10) . . . . ? O54 Cu3 N10 C9 -177.4(11) . . . . ? N40 Cu3 N10 C9 -70.4(10) . . . . ? Cu2 Cu3 N10 C9 -148.6(10) . . . . ? Cu1 Cu3 N10 C9 15.5(9) . . . . ? O24 Cu3 N10 C11 -81.4(8) . . . . ? O54 Cu3 N10 C11 8.4(18) . . . . ? N40 Cu3 N10 C11 115.3(8) . . . . ? Cu2 Cu3 N10 C11 37.2(8) . . . . ? Cu1 Cu3 N10 C11 -158.8(8) . . . . ? C9 N10 C11 C12 -1.8(18) . . . . ? Cu3 N10 C11 C12 172.9(9) . . . . ? C9 N10 C11 N15 177.2(10) . . . . ? Cu3 N10 C11 N15 -8.1(13) . . . . ? N10 C11 C12 C13 0.4(18) . . . . ? N15 C11 C12 C13 -178.4(12) . . . . ? C11 C12 C13 C14 -0.3(19) . . . . ? C12 C13 C14 C9 1(2) . . . . ? N10 C9 C14 C13 -2.7(18) . . . . ? N8 C9 C14 C13 -179.2(12) . . . . ? N10 C11 N15 C16 136.7(11) . . . . ? C12 C11 N15 C16 -44.4(18) . . . . ? N10 C11 N15 Cu2 -55.7(14) . . . . ? C12 C11 N15 Cu2 123.2(12) . . . . ? N45 Cu2 N15 C16 160.6(9) . . . . ? N18 Cu2 N15 C16 -13.4(9) . . . . ? O53 Cu2 N15 C16 -93.5(9) . . . . ? N48 Cu2 N15 C16 76.1(9) . . . . ? Cu3 Cu2 N15 C16 -128.9(9) . . . . ? N45 Cu2 N15 C11 -7.4(11) . . . . ? N18 Cu2 N15 C11 178.5(11) . . . . ? O53 Cu2 N15 C11 98.4(10) . . . . ? N48 Cu2 N15 C11 -92.0(10) . . . . ? Cu3 Cu2 N15 C11 63.0(9) . . . . ? C11 N15 C16 O16 0(2) . . . . ? Cu2 N15 C16 O16 -168.7(12) . . . . ? C11 N15 C16 C17 -173.3(11) . . . . ? Cu2 N15 C16 C17 17.6(13) . . . . ? O16 C16 C17 N18 171.7(12) . . . . ? N15 C16 C17 N18 -13.7(16) . . . . ? O16 C16 C17 C22 -8.4(19) . . . . ? N15 C16 C17 C22 166.2(12) . . . . ? C22 C17 N18 C19 -0.2(18) . . . . ? C16 C17 N18 C19 179.6(11) . . . . ? C22 C17 N18 Cu2 -177.5(10) . . . . ? C16 C17 N18 Cu2 2.4(14) . . . . ? N45 Cu2 N18 C19 76(4) . . . . ? O53 Cu2 N18 C19 -38.0(11) . . . . ? N15 Cu2 N18 C19 -171.7(11) . . . . ? N48 Cu2 N18 C19 80.0(11) . . . . ? Cu3 Cu2 N18 C19 -115.8(10) . . . . ? N45 Cu2 N18 C17 -107(4) . . . . ? O53 Cu2 N18 C17 139.1(9) . . . . ? N15 Cu2 N18 C17 5.3(9) . . . . ? N48 Cu2 N18 C17 -102.9(9) . . . . ? Cu3 Cu2 N18 C17 61.3(9) . . . . ? C17 N18 C19 C20 -0.7(19) . . . . ? Cu2 N18 C19 C20 176.2(9) . . . . ? N18 C19 C20 N21 1(2) . . . . ? C19 C20 N21 C22 0.0(19) . . . . ? C20 N21 C22 C17 -1.0(19) . . . . ? N18 C17 C22 N21 1(2) . . . . ? C16 C17 C22 N21 -178.7(12) . . . . ? N8 Cu1 O23 C23 105.6(11) . . . . ? N31 Cu1 O23 C23 -76.6(11) . . . . ? N38 Cu1 O23 C23 -2.0(12) . . . . ? N1 Cu1 O23 C23 -172.3(10) . . . . ? Cu3 Cu1 O23 C23 31.9(10) . . . . ? O54 Cu3 O24 C23 136.1(10) . . . . ? N10 Cu3 O24 C23 -60.5(10) . . . . ? N40 Cu3 O24 C23 50.9(18) . . . . ? Cu2 Cu3 O24 C23 -150.4(9) . . . . ? Cu1 Cu3 O24 C23 18.0(10) . . . . ? Cu1 O23 C23 O24 -31.4(18) . . . . ? Cu1 O23 C23 C24 148.2(10) . . . . ? Cu3 O24 C23 O23 -1.7(19) . . . . ? Cu3 O24 C23 C24 178.6(9) . . . . ? N8 Cu1 N31 C32 -117(10) . . . . ? O23 Cu1 N31 C32 127.7(9) . . . . ? N38 Cu1 N31 C32 1.7(9) . . . . ? N1 Cu1 N31 C32 -96.6(10) . . . . ? Cu3 Cu1 N31 C32 53.9(10) . . . . ? N8 Cu1 N31 C36 71(11) . . . . ? O23 Cu1 N31 C36 -45.1(11) . . . . ? N38 Cu1 N31 C36 -171.2(12) . . . . ? N1 Cu1 N31 C36 90.6(11) . . . . ? Cu3 Cu1 N31 C36 -119.0(11) . . . . ? C36 N31 C32 C33 -0.6(19) . . . . ? Cu1 N31 C32 C33 -174.2(10) . . . . ? C36 N31 C32 C37 176.9(11) . . . . ? Cu1 N31 C32 C37 3.3(15) . . . . ? N31 C32 C33 N34 -1(2) . . . . ? C37 C32 C33 N34 -178.4(13) . . . . ? C32 C33 N34 C35 1(2) . . . . ? C33 N34 C35 C36 0(2) . . . . ? C32 N31 C36 C35 1.8(19) . . . . ? Cu1 N31 C36 C35 174.6(10) . . . . ? N34 C35 C36 N31 -2(2) . . . . ? N31 C32 C37 O37 172.5(12) . . . . ? C33 C32 C37 O37 -10(2) . . . . ? N31 C32 C37 N38 -9.2(17) . . . . ? C33 C32 C37 N38 168.2(12) . . . . ? O37 C37 N38 C39 -4(2) . . . . ? C32 C37 N38 C39 178.1(11) . . . . ? O37 C37 N38 Cu1 -171.5(11) . . . . ? C32 C37 N38 Cu1 10.4(14) . . . . ? N8 Cu1 N38 C37 170.8(9) . . . . ? O23 Cu1 N38 C37 -85.5(9) . . . . ? N31 Cu1 N38 C37 -7.0(9) . . . . ? N1 Cu1 N38 C37 87.7(9) . . . . ? Cu3 Cu1 N38 C37 -124.7(9) . . . . ? N8 Cu1 N38 C39 3.6(10) . . . . ? O23 Cu1 N38 C39 107.4(10) . . . . ? N31 Cu1 N38 C39 -174.1(10) . . . . ? N1 Cu1 N38 C39 -79.5(10) . . . . ? Cu3 Cu1 N38 C39 68.1(9) . . . . ? C37 N38 C39 N40 129.0(12) . . . . ? Cu1 N38 C39 N40 -64.6(13) . . . . ? C37 N38 C39 C44 -54.0(17) . . . . ? Cu1 N38 C39 C44 112.5(12) . . . . ? C44 C39 N40 C41 -0.2(19) . . . . ? N38 C39 N40 C41 177.0(10) . . . . ? C44 C39 N40 Cu3 178.2(10) . . . . ? N38 C39 N40 Cu3 -4.7(13) . . . . ? O24 Cu3 N40 C39 4.0(18) . . . . ? O54 Cu3 N40 C39 -80.4(8) . . . . ? N10 Cu3 N40 C39 115.5(9) . . . . ? Cu2 Cu3 N40 C39 -157.0(8) . . . . ? Cu1 Cu3 N40 C39 36.2(8) . . . . ? O24 Cu3 N40 C41 -177.8(11) . . . . ? O54 Cu3 N40 C41 97.8(10) . . . . ? N10 Cu3 N40 C41 -66.3(11) . . . . ? Cu2 Cu3 N40 C41 21.2(10) . . . . ? Cu1 Cu3 N40 C41 -145.6(10) . . . . ? C39 N40 C41 N45 176.2(11) . . . . ? Cu3 N40 C41 N45 -1.9(16) . . . . ? C39 N40 C41 C42 -1.0(17) . . . . ? Cu3 N40 C41 C42 -179.0(8) . . . . ? N40 C41 C42 C43 1.7(18) . . . . ? N45 C41 C42 C43 -175.2(12) . . . . ? C41 C42 C43 C44 -1.3(18) . . . . ? N40 C39 C44 C43 0.6(19) . . . . ? N38 C39 C44 C43 -176.2(12) . . . . ? C42 C43 C44 C39 0.2(19) . . . . ? N40 C41 N45 C46 158.7(11) . . . . ? C42 C41 N45 C46 -24.4(18) . . . . ? N40 C41 N45 Cu2 -34.6(14) . . . . ? C42 C41 N45 Cu2 142.3(10) . . . . ? N18 Cu2 N45 C46 14(4) . . . . ? O53 Cu2 N45 C46 127.3(9) . . . . ? N15 Cu2 N45 C46 -97.6(9) . . . . ? N48 Cu2 N45 C46 9.4(9) . . . . ? Cu3 Cu2 N45 C46 -155.0(9) . . . . ? N18 Cu2 N45 C41 -154(4) . . . . ? O53 Cu2 N45 C41 -40.2(9) . . . . ? N15 Cu2 N45 C41 94.9(9) . . . . ? N48 Cu2 N45 C41 -158.1(10) . . . . ? Cu3 Cu2 N45 C41 37.4(9) . . . . ? C41 N45 C46 O46 -16(2) . . . . ? Cu2 N45 C46 O46 176.5(10) . . . . ? C41 N45 C46 C47 159.4(11) . . . . ? Cu2 N45 C46 C47 -8.2(14) . . . . ? O46 C46 C47 N48 175.6(12) . . . . ? N45 C46 C47 N48 0.1(17) . . . . ? O46 C46 C47 C52 -1.9(19) . . . . ? N45 C46 C47 C52 -177.4(12) . . . . ? C52 C47 N48 C49 0.6(18) . . . . ? C46 C47 N48 C49 -176.9(11) . . . . ? C52 C47 N48 Cu2 -175.1(10) . . . . ? C46 C47 N48 Cu2 7.5(14) . . . . ? N45 Cu2 N48 C49 176.2(12) . . . . ? N18 Cu2 N48 C49 -3.3(12) . . . . ? O53 Cu2 N48 C49 87.8(12) . . . . ? N15 Cu2 N48 C49 -83.6(12) . . . . ? Cu3 Cu2 N48 C49 -145.3(9) . . . . ? N45 Cu2 N48 C47 -9.1(8) . . . . ? N18 Cu2 N48 C47 171.4(9) . . . . ? O53 Cu2 N48 C47 -97.5(8) . . . . ? N15 Cu2 N48 C47 91.1(8) . . . . ? Cu3 Cu2 N48 C47 29.5(13) . . . . ? C47 N48 C49 C50 0.9(18) . . . . ? Cu2 N48 C49 C50 175.4(9) . . . . ? N48 C49 C50 N51 -1(2) . . . . ? C49 C50 N51 C52 -0.4(19) . . . . ? C50 N51 C52 C47 1.9(19) . . . . ? N48 C47 C52 N51 -2(2) . . . . ? C46 C47 C52 N51 175.4(12) . . . . ? N45 Cu2 O53 C53 99.4(9) . . . . ? N18 Cu2 O53 C53 -86.3(9) . . . . ? N15 Cu2 O53 C53 -10.4(11) . . . . ? N48 Cu2 O53 C53 -179.2(8) . . . . ? Cu3 Cu2 O53 C53 20.9(8) . . . . ? O24 Cu3 O54 C53 155.5(10) . . . . ? N10 Cu3 O54 C53 64.7(17) . . . . ? N40 Cu3 O54 C53 -42.4(10) . . . . ? Cu2 Cu3 O54 C53 35.1(9) . . . . ? Cu1 Cu3 O54 C53 -129.4(9) . . . . ? Cu2 O53 C53 O54 -2.7(17) . . . . ? Cu2 O53 C53 C54 -177.4(8) . . . . ? Cu3 O54 C53 O53 -33.4(17) . . . . ? Cu3 O54 C53 C54 141.5(9) . . . . ? O113 Cu5 Cu6 O84 -107.7(4) . . . . ? N105 Cu5 Cu6 O84 155.2(4) . . . . ? N78 Cu5 Cu6 O84 -19.3(4) . . . . ? N75 Cu5 Cu6 O84 52.6(4) . . . . ? N108 Cu5 Cu6 O84 112.4(6) . . . . ? O113 Cu5 Cu6 O114 -24.0(3) . . . . ? N105 Cu5 Cu6 O114 -121.1(4) . . . . ? N78 Cu5 Cu6 O114 64.3(4) . . . . ? N75 Cu5 Cu6 O114 136.2(4) . . . . ? N108 Cu5 Cu6 O114 -163.9(6) . . . . ? O113 Cu5 Cu6 N70 162.5(4) . . . . ? N105 Cu5 Cu6 N70 65.4(4) . . . . ? N78 Cu5 Cu6 N70 -109.1(4) . . . . ? N75 Cu5 Cu6 N70 -37.3(4) . . . . ? N108 Cu5 Cu6 N70 22.6(7) . . . . ? O113 Cu5 Cu6 N100 71.9(4) . . . . ? N105 Cu5 Cu6 N100 -25.2(4) . . . . ? N78 Cu5 Cu6 N100 160.3(4) . . . . ? N75 Cu5 Cu6 N100 -127.9(4) . . . . ? N108 Cu5 Cu6 N100 -68.0(7) . . . . ? O113 Cu5 Cu6 Cu4 116.6(3) . . . . ? N105 Cu5 Cu6 Cu4 19.5(4) . . . . ? N78 Cu5 Cu6 Cu4 -155.1(4) . . . . ? N75 Cu5 Cu6 Cu4 -83.2(4) . . . . ? N108 Cu5 Cu6 Cu4 -23.4(7) . . . . ? N68 Cu4 Cu6 O84 -115.2(4) . . . . ? N91 Cu4 Cu6 O84 67.5(4) . . . . ? O83 Cu4 Cu6 O84 -20.4(4) . . . . ? N98 Cu4 Cu6 O84 137.0(4) . . . . ? N61 Cu4 Cu6 O84 -163.4(6) . . . . ? N68 Cu4 Cu6 O114 160.9(4) . . . . ? N91 Cu4 Cu6 O114 -16.4(4) . . . . ? O83 Cu4 Cu6 O114 -104.3(4) . . . . ? N98 Cu4 Cu6 O114 53.0(4) . . . . ? N61 Cu4 Cu6 O114 112.6(6) . . . . ? N68 Cu4 Cu6 N70 -22.9(4) . . . . ? N91 Cu4 Cu6 N70 159.7(4) . . . . ? O83 Cu4 Cu6 N70 71.9(4) . . . . ? N98 Cu4 Cu6 N70 -130.8(4) . . . . ? N61 Cu4 Cu6 N70 -71.2(6) . . . . ? N68 Cu4 Cu6 N100 67.8(4) . . . . ? N91 Cu4 Cu6 N100 -109.5(4) . . . . ? O83 Cu4 Cu6 N100 162.6(4) . . . . ? N98 Cu4 Cu6 N100 -40.0(4) . . . . ? N61 Cu4 Cu6 N100 19.6(7) . . . . ? N68 Cu4 Cu6 Cu5 24.0(4) . . . . ? N91 Cu4 Cu6 Cu5 -153.4(4) . . . . ? O83 Cu4 Cu6 Cu5 118.8(4) . . . . ? N98 Cu4 Cu6 Cu5 -83.9(4) . . . . ? N61 Cu4 Cu6 Cu5 -24.3(7) . . . . ? N68 Cu4 N61 C62 -6.6(8) . . . . ? N91 Cu4 N61 C62 173.1(8) . . . . ? O83 Cu4 N61 C62 -94.5(9) . . . . ? N98 Cu4 N61 C62 92.9(9) . . . . ? Cu6 Cu4 N61 C62 41.5(12) . . . . ? N68 Cu4 N61 C66 -177.2(12) . . . . ? N91 Cu4 N61 C66 2.5(12) . . . . ? O83 Cu4 N61 C66 94.9(12) . . . . ? N98 Cu4 N61 C66 -77.7(12) . . . . ? Cu6 Cu4 N61 C66 -129.1(10) . . . . ? C66 N61 C62 C63 -2.9(18) . . . . ? Cu4 N61 C62 C63 -175.3(10) . . . . ? C66 N61 C62 C67 177.2(11) . . . . ? Cu4 N61 C62 C67 4.7(13) . . . . ? N61 C62 C63 N64 1(2) . . . . ? C67 C62 C63 N64 -179.3(12) . . . . ? C62 C63 N64 C65 1.6(19) . . . . ? C63 N64 C65 C66 -2(2) . . . . ? C62 N61 C66 C65 2.9(18) . . . . ? Cu4 N61 C66 C65 173.0(9) . . . . ? N64 C65 C66 N61 -1(2) . . . . ? N61 C62 C67 O67 178.4(11) . . . . ? C63 C62 C67 O67 -1.5(18) . . . . ? N61 C62 C67 N68 1.2(16) . . . . ? C63 C62 C67 N68 -178.7(11) . . . . ? O67 C67 N68 C69 -11.7(19) . . . . ? C62 C67 N68 C69 165.1(11) . . . . ? O67 C67 N68 Cu4 175.7(11) . . . . ? C62 C67 N68 Cu4 -7.5(13) . . . . ? N91 Cu4 N68 C67 5(4) . . . . ? O83 Cu4 N68 C67 129.4(9) . . . . ? N98 Cu4 N68 C67 -91.7(9) . . . . ? N61 Cu4 N68 C67 7.8(9) . . . . ? Cu6 Cu4 N68 C67 -151.3(9) . . . . ? N91 Cu4 N68 C69 -167(3) . . . . ? O83 Cu4 N68 C69 -42.9(10) . . . . ? N98 Cu4 N68 C69 96.1(10) . . . . ? N61 Cu4 N68 C69 -164.4(10) . . . . ? Cu6 Cu4 N68 C69 36.5(9) . . . . ? C67 N68 C69 N70 153.7(11) . . . . ? Cu4 N68 C69 N70 -34.2(14) . . . . ? C67 N68 C69 C74 -31.0(18) . . . . ? Cu4 N68 C69 C74 141.1(10) . . . . ? C74 C69 N70 C71 2.5(17) . . . . ? N68 C69 N70 C71 178.0(10) . . . . ? C74 C69 N70 Cu6 -175.5(8) . . . . ? N68 C69 N70 Cu6 0.0(15) . . . . ? O84 Cu6 N70 C71 -80.5(8) . . . . ? O114 Cu6 N70 C71 7.4(19) . . . . ? N100 Cu6 N70 C71 112.7(8) . . . . ? Cu5 Cu6 N70 C71 32.6(8) . . . . ? Cu4 Cu6 N70 C71 -159.2(8) . . . . ? O84 Cu6 N70 C69 97.7(10) . . . . ? O114 Cu6 N70 C69 -174.4(12) . . . . ? N100 Cu6 N70 C69 -69.1(10) . . . . ? Cu5 Cu6 N70 C69 -149.2(10) . . . . ? Cu4 Cu6 N70 C69 19.0(9) . . . . ? C69 N70 C71 C72 -2.9(17) . . . . ? Cu6 N70 C71 C72 175.5(9) . . . . ? C69 N70 C71 N75 177.4(10) . . . . ? Cu6 N70 C71 N75 -4.3(12) . . . . ? N70 C71 C72 C73 1.0(18) . . . . ? N75 C71 C72 C73 -179.3(11) . . . . ? C71 C72 C73 C74 1.2(18) . . . . ? C72 C73 C74 C69 -1.5(18) . . . . ? N70 C69 C74 C73 -0.4(18) . . . . ? N68 C69 C74 C73 -175.5(11) . . . . ? N70 C71 N75 C76 137.9(11) . . . . ? C72 C71 N75 C76 -41.8(16) . . . . ? N70 C71 N75 Cu5 -52.5(13) . . . . ? C72 C71 N75 Cu5 127.7(11) . . . . ? O113 Cu5 N75 C76 -97.8(10) . . . . ? N105 Cu5 N75 C76 151.9(8) . . . . ? N78 Cu5 N75 C76 -19.0(8) . . . . ? N108 Cu5 N75 C76 71.6(9) . . . . ? Cu6 Cu5 N75 C76 -131.2(9) . . . . ? O113 Cu5 N75 C71 92.4(10) . . . . ? N105 Cu5 N75 C71 -18.0(10) . . . . ? N78 Cu5 N75 C71 171.1(10) . . . . ? N108 Cu5 N75 C71 -98.3(9) . . . . ? Cu6 Cu5 N75 C71 58.9(9) . . . . ? C71 N75 C76 O76 0(2) . . . . ? Cu5 N75 C76 O76 -171.1(12) . . . . ? C71 N75 C76 C77 -174.7(9) . . . . ? Cu5 N75 C76 C77 14.5(12) . . . . ? O76 C76 C77 N78 -173.4(11) . . . . ? N75 C76 C77 N78 1.7(15) . . . . ? O76 C76 C77 C82 3.9(19) . . . . ? N75 C76 C77 C82 179.0(11) . . . . ? C82 C77 N78 C79 -3.8(17) . . . . ? C76 C77 N78 C79 173.5(10) . . . . ? C82 C77 N78 Cu5 165.5(10) . . . . ? C76 C77 N78 Cu5 -17.2(13) . . . . ? O113 Cu5 N78 C79 -29.7(11) . . . . ? N105 Cu5 N78 C79 105(3) . . . . ? N75 Cu5 N78 C79 -173.2(11) . . . . ? N108 Cu5 N78 C79 87.6(11) . . . . ? Cu6 Cu5 N78 C79 -111.6(10) . . . . ? O113 Cu5 N78 C77 162.7(8) . . . . ? N105 Cu5 N78 C77 -63(3) . . . . ? N75 Cu5 N78 C77 19.3(8) . . . . ? N108 Cu5 N78 C77 -79.9(8) . . . . ? Cu6 Cu5 N78 C77 80.9(8) . . . . ? C77 N78 C79 C80 4.4(17) . . . . ? Cu5 N78 C79 C80 -162.8(9) . . . . ? N78 C79 C80 N81 -2(2) . . . . ? C79 C80 N81 C82 -1(2) . . . . ? C80 N81 C82 C77 2.1(19) . . . . ? N78 C77 C82 N81 0.6(19) . . . . ? C76 C77 C82 N81 -176.5(12) . . . . ? N68 Cu4 O83 C83 99.7(10) . . . . ? N91 Cu4 O83 C83 -85.6(10) . . . . ? N98 Cu4 O83 C83 -9.9(12) . . . . ? N61 Cu4 O83 C83 -179.2(9) . . . . ? Cu6 Cu4 O83 C83 20.2(9) . . . . ? O114 Cu6 O84 C83 144.3(10) . . . . ? N70 Cu6 O84 C83 -50.8(10) . . . . ? N100 Cu6 O84 C83 42(2) . . . . ? Cu5 Cu6 O84 C83 -139.8(9) . . . . ? Cu4 Cu6 O84 C83 28.7(9) . . . . ? Cu4 O83 C83 O84 -6.5(17) . . . . ? Cu4 O83 C83 C84 178.8(9) . . . . ? Cu6 O84 C83 O83 -24.4(17) . . . . ? Cu6 O84 C83 C84 150.4(10) . . . . ? N68 Cu4 N91 C96 86(4) . . . . ? O83 Cu4 N91 C96 -38.0(11) . . . . ? N98 Cu4 N91 C96 -175.6(11) . . . . ? N61 Cu4 N91 C96 83.7(11) . . . . ? Cu6 Cu4 N91 C96 -117.8(10) . . . . ? N68 Cu4 N91 C92 -89(4) . . . . ? O83 Cu4 N91 C92 146.6(9) . . . . ? N98 Cu4 N91 C92 8.9(8) . . . . ? N61 Cu4 N91 C92 -91.8(9) . . . . ? Cu6 Cu4 N91 C92 66.7(9) . . . . ? C96 N91 C92 C93 -4.2(17) . . . . ? Cu4 N91 C92 C93 171.8(10) . . . . ? C96 N91 C92 C97 176.5(10) . . . . ? Cu4 N91 C92 C97 -7.4(13) . . . . ? N91 C92 C93 N94 3.1(19) . . . . ? C97 C92 C93 N94 -177.8(11) . . . . ? C92 C93 N94 C95 -1.3(19) . . . . ? C93 N94 C95 C96 1.1(19) . . . . ? C92 N91 C96 C95 4.0(18) . . . . ? Cu4 N91 C96 C95 -171.5(10) . . . . ? N94 C95 C96 N91 -3(2) . . . . ? N91 C92 C97 O97 179.7(11) . . . . ? C93 C92 C97 O97 0.5(19) . . . . ? N91 C92 C97 N98 -0.4(15) . . . . ? C93 C92 C97 N98 -179.6(11) . . . . ? O97 C97 N98 C99 1.3(19) . . . . ? C92 C97 N98 C99 -178.6(10) . . . . ? O97 C97 N98 Cu4 -172.4(11) . . . . ? C92 C97 N98 Cu4 7.7(13) . . . . ? N68 Cu4 N98 C97 164.4(9) . . . . ? N91 Cu4 N98 C97 -9.2(8) . . . . ? O83 Cu4 N98 C97 -89.1(10) . . . . ? N61 Cu4 N98 C97 81.7(9) . . . . ? Cu6 Cu4 N98 C97 -122.8(9) . . . . ? N68 Cu4 N98 C99 -9.0(10) . . . . ? N91 Cu4 N98 C99 177.5(10) . . . . ? O83 Cu4 N98 C99 97.6(10) . . . . ? N61 Cu4 N98 C99 -91.7(10) . . . . ? Cu6 Cu4 N98 C99 63.9(9) . . . . ? C97 N98 C99 N100 127.2(12) . . . . ? Cu4 N98 C99 N100 -59.7(14) . . . . ? C97 N98 C99 C104 -59.4(17) . . . . ? Cu4 N98 C99 C104 113.7(13) . . . . ? C104 C99 N100 C101 -0.3(19) . . . . ? N98 C99 N100 C101 173.3(11) . . . . ? C104 C99 N100 Cu6 -176.4(10) . . . . ? N98 C99 N100 Cu6 -2.8(13) . . . . ? O84 Cu6 N100 C99 20(2) . . . . ? O114 Cu6 N100 C99 -81.8(8) . . . . ? N70 Cu6 N100 C99 112.8(9) . . . . ? Cu5 Cu6 N100 C99 -158.2(8) . . . . ? Cu4 Cu6 N100 C99 33.1(8) . . . . ? O84 Cu6 N100 C101 -155.8(15) . . . . ? O114 Cu6 N100 C101 102.4(10) . . . . ? N70 Cu6 N100 C101 -63.0(10) . . . . ? Cu5 Cu6 N100 C101 25.9(10) . . . . ? Cu4 Cu6 N100 C101 -142.8(10) . . . . ? C99 N100 C101 C102 -0.4(18) . . . . ? Cu6 N100 C101 C102 174.9(9) . . . . ? C99 N100 C101 N105 175.9(11) . . . . ? Cu6 N100 C101 N105 -8.7(16) . . . . ? N100 C101 C102 C103 1.1(18) . . . . ? N105 C101 C102 C103 -174.8(12) . . . . ? C101 C102 C103 C104 -1.0(19) . . . . ? N100 C99 C104 C103 0.4(18) . . . . ? N98 C99 C104 C103 -172.5(11) . . . . ? C102 C103 C104 C99 0.2(18) . . . . ? N100 C101 N105 C106 154.1(11) . . . . ? C102 C101 N105 C106 -30.0(19) . . . . ? N100 C101 N105 Cu5 -27.6(14) . . . . ? C102 C101 N105 Cu5 148.3(11) . . . . ? O113 Cu5 N105 C106 132.7(9) . . . . ? N78 Cu5 N105 C106 -1(3) . . . . ? N75 Cu5 N105 C106 -82.2(9) . . . . ? N108 Cu5 N105 C106 15.9(8) . . . . ? Cu6 Cu5 N105 C106 -146.3(9) . . . . ? O113 Cu5 N105 C101 -45.7(9) . . . . ? N78 Cu5 N105 C101 -180(2) . . . . ? N75 Cu5 N105 C101 99.4(9) . . . . ? N108 Cu5 N105 C101 -162.5(9) . . . . ? Cu6 Cu5 N105 C101 35.3(9) . . . . ? C101 N105 C106 O106 -12.9(19) . . . . ? Cu5 N105 C106 O106 168.7(10) . . . . ? C101 N105 C106 C107 166.9(11) . . . . ? Cu5 N105 C106 C107 -11.5(14) . . . . ? O106 C106 C107 N108 174.4(11) . . . . ? N105 C106 C107 N108 -5.4(17) . . . . ? O106 C106 C107 C112 -1.1(19) . . . . ? N105 C106 C107 C112 179.1(12) . . . . ? C112 C107 N108 C109 0.8(18) . . . . ? C106 C107 N108 C109 -174.8(11) . . . . ? C112 C107 N108 Cu5 -167.4(10) . . . . ? C106 C107 N108 Cu5 17.0(13) . . . . ? O113 Cu5 N108 C107 -108.3(8) . . . . ? N105 Cu5 N108 C107 -17.4(8) . . . . ? N78 Cu5 N108 C107 159.9(8) . . . . ? N75 Cu5 N108 C107 78.9(8) . . . . ? Cu6 Cu5 N108 C107 25.8(12) . . . . ? O113 Cu5 N108 C109 85.8(11) . . . . ? N105 Cu5 N108 C109 176.8(11) . . . . ? N78 Cu5 N108 C109 -5.9(11) . . . . ? N75 Cu5 N108 C109 -86.9(11) . . . . ? Cu6 Cu5 N108 C109 -140.0(9) . . . . ? C107 N108 C109 C110 0.1(17) . . . . ? Cu5 N108 C109 C110 164.7(9) . . . . ? N108 C109 C110 N111 -1(2) . . . . ? C109 C110 N111 C112 1.3(19) . . . . ? C110 N111 C112 C107 -0.4(19) . . . . ? N108 C107 C112 N111 -1(2) . . . . ? C106 C107 C112 N111 174.8(12) . . . . ? N105 Cu5 O113 C113 108.2(9) . . . . ? N78 Cu5 O113 C113 -78.3(9) . . . . ? N75 Cu5 O113 C113 -2.8(12) . . . . ? N108 Cu5 O113 C113 -170.9(9) . . . . ? Cu6 Cu5 O113 C113 27.8(9) . . . . ? O84 Cu6 O114 C113 144.2(10) . . . . ? N70 Cu6 O114 C113 56.2(19) . . . . ? N100 Cu6 O114 C113 -48.7(10) . . . . ? Cu5 Cu6 O114 C113 30.3(9) . . . . ? Cu4 Cu6 O114 C113 -138.4(9) . . . . ? Cu5 O113 C113 O114 -15.4(17) . . . . ? Cu5 O113 C113 C114 159.7(9) . . . . ? Cu6 O114 C113 O113 -19.9(18) . . . . ? Cu6 O114 C113 C114 164.9(9) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 23.46 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.035 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.172 data_4 _database_code_depnum_ccdc_archive 'CCDC 227114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 Cu N4 O2' _chemical_formula_sum 'C19 H14 Cu N4 O2' _chemical_formula_weight 393.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.777(5) _cell_length_b 12.749(3) _cell_length_c 6.8213(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1633.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description needle _exptl_crystal_colour red/orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.709668 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6185 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 23.38 _reflns_number_total 1123 _reflns_number_gt 790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0478P)^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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1123 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.93711(5) 0.2500 0.0203(2) Uani 1 2 d S . . N1 N 0.41566(16) 0.8479(3) 0.1710(5) 0.0251(8) Uani 1 1 d . . . C2 C 0.36208(19) 0.9100(3) 0.1013(5) 0.0232(9) Uani 1 1 d . . . C3 C 0.2992(2) 0.8663(4) 0.0346(6) 0.0313(11) Uani 1 1 d . . . H3A H 0.2629 0.9102 -0.0173 0.038 Uiso 1 1 calc R . . C4 C 0.2891(2) 0.7598(4) 0.0430(6) 0.0416(12) Uani 1 1 d . . . H4A H 0.2460 0.7292 -0.0025 0.050 Uiso 1 1 calc R . . C5 C 0.3424(2) 0.6985(4) 0.1186(5) 0.0361(11) Uani 1 1 d . . . H5A H 0.3362 0.6248 0.1293 0.043 Uiso 1 1 calc R . . C6 C 0.4053(2) 0.7452(3) 0.1792(6) 0.0311(10) Uani 1 1 d . . . H6A H 0.4425 0.7019 0.2284 0.037 Uiso 1 1 calc R . . O7 O 0.32473(14) 1.0846(2) 0.0500(4) 0.0318(7) Uani 1 1 d . . . C7 C 0.37306(19) 1.0254(3) 0.1050(5) 0.0224(9) Uani 1 1 d . . . N8 N 0.43793(16) 1.0506(2) 0.1732(5) 0.0229(8) Uani 1 1 d . . . C9 C 0.4648(2) 1.1510(3) 0.2067(5) 0.0233(9) Uani 1 1 d . . . C10 C 0.4320(2) 1.2463(3) 0.1708(5) 0.0276(10) Uani 1 1 d . . . H10A H 0.3853 1.2472 0.1177 0.033 Uiso 1 1 calc R . . C11 C 0.4660(2) 1.3405(3) 0.2107(5) 0.0331(11) Uani 1 1 d . . . C12 C 0.4277(5) 1.4395(7) 0.1807(15) 0.048(3) Uani 0.50 1 d P . . H12A H 0.4588 1.4984 0.2154 0.073 Uiso 0.50 1 calc PR . . H12B H 0.3851 1.4407 0.2638 0.073 Uiso 0.50 1 calc PR . . H12C H 0.4136 1.4454 0.0428 0.073 Uiso 0.50 1 calc PR . . 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 0.0203(3) 0.0260(4) 0.0145(3) 0.000 -0.0005(3) 0.000 N1 0.0236(18) 0.037(2) 0.0145(15) -0.0042(14) 0.0020(13) -0.0051(16) C2 0.018(2) 0.040(3) 0.0122(19) -0.0003(18) 0.0046(16) -0.0007(18) C3 0.026(2) 0.056(3) 0.0123(19) 0.000(2) 0.0075(18) -0.0078(19) C4 0.038(3) 0.059(4) 0.028(2) -0.007(2) 0.006(2) -0.021(2) C5 0.048(3) 0.034(3) 0.026(2) -0.001(2) 0.011(2) -0.018(2) C6 0.039(3) 0.033(3) 0.022(2) -0.0057(18) 0.0079(17) -0.006(2) O7 0.0267(15) 0.0457(18) 0.0229(14) 0.0018(13) -0.0015(14) 0.0068(14) C7 0.018(2) 0.043(3) 0.0070(19) -0.0007(17) 0.0059(16) -0.0001(19) N8 0.0209(17) 0.026(2) 0.0219(16) -0.0011(14) 0.0010(13) -0.0056(14) C9 0.0259(19) 0.032(3) 0.012(2) 0.0003(16) 0.0069(15) -0.0005(18) C10 0.033(2) 0.033(3) 0.0166(19) 0.0006(18) 0.0048(18) 0.007(2) C11 0.052(2) 0.026(3) 0.021(3) 0.0018(18) 0.0048(18) 0.0062(19) C12 0.051(6) 0.041(6) 0.054(6) 0.006(5) 0.004(5) -0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N8 1.930(3) 3_655 ? Cu1 N8 1.930(3) . ? Cu1 N1 2.023(3) . ? Cu1 N1 2.023(3) 3_655 ? N1 C6 1.325(5) . ? N1 C2 1.365(5) . ? C2 C3 1.383(5) . ? C2 C7 1.486(6) . ? C3 C4 1.373(6) . ? C3 H3A 0.9500 . ? C4 C5 1.370(6) . ? C4 H4A 0.9500 . ? C5 C6 1.387(6) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? O7 C7 1.238(4) . ? C7 N8 1.343(5) . ? N8 C9 1.395(5) . ? C9 C10 1.383(6) . ? C9 C9 1.449(8) 3_655 ? C10 C11 1.388(6) . ? C10 H10A 0.9500 . ? C11 C11 1.385(9) 3_655 ? C11 C12 1.466(10) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Cu1 N8 82.92(18) 3_655 . ? N8 Cu1 N1 165.11(13) 3_655 . ? N8 Cu1 N1 82.89(14) . . ? N8 Cu1 N1 82.89(14) 3_655 3_655 ? N8 Cu1 N1 165.11(13) . 3_655 ? N1 Cu1 N1 111.59(19) . 3_655 ? C6 N1 C2 118.7(3) . . ? C6 N1 Cu1 131.2(3) . . ? C2 N1 Cu1 110.1(3) . . ? N1 C2 C3 120.7(4) . . ? N1 C2 C7 117.8(3) . . ? C3 C2 C7 121.5(4) . . ? C4 C3 C2 120.2(4) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? N1 C6 C5 122.4(4) . . ? N1 C6 H6A 118.8 . . ? C5 C6 H6A 118.8 . . ? O7 C7 N8 128.6(4) . . ? O7 C7 C2 119.8(3) . . ? N8 C7 C2 111.6(3) . . ? C7 N8 C9 127.1(3) . . ? C7 N8 Cu1 117.6(3) . . ? C9 N8 Cu1 115.2(2) . . ? C10 C9 N8 128.1(4) . . ? C10 C9 C9 118.5(2) . 3_655 ? N8 C9 C9 113.4(2) . 3_655 ? C9 C10 C11 121.5(4) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C11 C11 C10 120.0(2) 3_655 . ? C11 C11 C12 120.4(4) 3_655 . ? C10 C11 C12 119.5(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 N8 Cu1 N1 C6 -159.3(4) 3_655 . . . ? N8 Cu1 N1 C6 -177.0(4) . . . . ? N1 Cu1 N1 C6 6.6(3) 3_655 . . . ? N8 Cu1 N1 C2 19.7(6) 3_655 . . . ? N8 Cu1 N1 C2 2.0(3) . . . . ? N1 Cu1 N1 C2 -174.4(3) 3_655 . . . ? C6 N1 C2 C3 -2.1(5) . . . . ? Cu1 N1 C2 C3 178.8(3) . . . . ? C6 N1 C2 C7 176.3(3) . . . . ? Cu1 N1 C2 C7 -2.9(4) . . . . ? N1 C2 C3 C4 1.9(6) . . . . ? C7 C2 C3 C4 -176.4(4) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 C6 -1.7(6) . . . . ? C2 N1 C6 C5 0.4(6) . . . . ? Cu1 N1 C6 C5 179.3(3) . . . . ? C4 C5 C6 N1 1.5(6) . . . . ? N1 C2 C7 O7 -177.3(3) . . . . ? C3 C2 C7 O7 1.1(5) . . . . ? N1 C2 C7 N8 2.3(4) . . . . ? C3 C2 C7 N8 -179.4(3) . . . . ? O7 C7 N8 C9 3.3(6) . . . . ? C2 C7 N8 C9 -176.2(3) . . . . ? O7 C7 N8 Cu1 179.1(3) . . . . ? C2 C7 N8 Cu1 -0.4(4) . . . . ? N8 Cu1 N8 C7 -176.4(4) 3_655 . . . ? N1 Cu1 N8 C7 -0.9(3) . . . . ? N1 Cu1 N8 C7 165.9(4) 3_655 . . . ? N8 Cu1 N8 C9 -0.07(16) 3_655 . . . ? N1 Cu1 N8 C9 175.4(2) . . . . ? N1 Cu1 N8 C9 -17.7(6) 3_655 . . . ? C7 N8 C9 C10 -2.6(6) . . . . ? Cu1 N8 C9 C10 -178.5(3) . . . . ? C7 N8 C9 C9 176.1(4) . . . 3_655 ? Cu1 N8 C9 C9 0.2(4) . . . 3_655 ? N8 C9 C10 C11 -179.5(3) . . . . ? C9 C9 C10 C11 1.9(6) 3_655 . . . ? C9 C10 C11 C11 -0.4(7) . . . 3_655 ? C9 C10 C11 C12 -176.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 23.38 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.310 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.067 data_5 _database_code_depnum_ccdc_archive 'CCDC 227115' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H26 Cu2 N10 O6.2[H2 O]' _chemical_formula_sum 'C34 H30 Cu2 N10 O8' _chemical_formula_weight 833.76 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.377(4) _cell_length_b 8.9474(15) _cell_length_c 19.422(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.094(5) _cell_angle_gamma 90.00 _cell_volume 3188.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 53 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 1.408 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.53271 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7579 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 23.30 _reflns_number_total 2249 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0724P)^2^+11.4952P] 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 2249 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.98409(3) 0.01230(6) 0.34142(3) 0.0185(3) Uani 1 1 d . . . N1 N 0.9508(2) 0.1841(4) 0.17494(19) 0.0190(9) Uani 1 1 d . . . C2 C 0.8996(2) 0.1625(5) 0.2203(2) 0.0170(10) Uani 1 1 d . . . C3 C 0.8450(2) 0.2558(4) 0.2305(2) 0.0078(8) Uani 1 1 d . . . H3A H 0.8099 0.2350 0.2633 0.009 Uiso 1 1 calc R . . C4 C 0.8417(2) 0.3806(5) 0.1923(2) 0.0239(11) Uani 1 1 d . . . H4A H 0.8026 0.4485 0.1976 0.029 Uiso 1 1 calc R . . C5 C 0.8931(3) 0.4139(6) 0.1454(3) 0.0287(12) Uani 1 1 d . . . H5A H 0.8911 0.5042 0.1197 0.034 Uiso 1 1 calc R . . C6 C 0.9479(3) 0.3097(5) 0.1376(3) 0.0265(11) Uani 1 1 d . . . H6A H 0.9838 0.3279 0.1052 0.032 Uiso 1 1 calc R . . N7 N 0.9084(2) 0.0337(4) 0.26068(19) 0.0180(8) Uani 1 1 d . . . O8 O 0.79825(17) -0.0688(4) 0.22095(16) 0.0242(8) Uani 1 1 d . . . C8 C 0.8551(2) -0.0675(5) 0.2587(2) 0.0190(10) Uani 1 1 d . . . C9 C 0.8717(2) -0.1975(5) 0.3075(2) 0.0196(10) Uani 1 1 d . . . N10 N 0.9329(2) -0.1753(4) 0.34701(19) 0.0209(9) Uani 1 1 d . . . C11 C 0.9574(3) -0.2766(5) 0.3933(2) 0.0208(11) Uani 1 1 d . . . C12 C 0.9215(3) -0.4095(5) 0.4013(2) 0.0242(11) Uani 1 1 d . . . H12A H 0.9391 -0.4817 0.4339 0.029 Uiso 1 1 calc R . . C13 C 0.8581(3) -0.4351(6) 0.3598(2) 0.0247(11) Uani 1 1 d . . . H13A H 0.8323 -0.5265 0.3638 0.030 Uiso 1 1 calc R . . C14 C 0.8324(3) -0.3270(5) 0.3125(2) 0.0237(11) Uani 1 1 d . . . H14A H 0.7890 -0.3428 0.2846 0.028 Uiso 1 1 calc R . . O15 O 1.05362(18) -0.3111(4) 0.47845(16) 0.0278(8) Uani 1 1 d . . . C15 C 1.0270(3) -0.2276(6) 0.4319(2) 0.0235(11) Uani 1 1 d . . . N16 N 1.0498(2) -0.0947(4) 0.41233(19) 0.0226(9) Uani 1 1 d . . . C17 C 1.1161(3) -0.0409(7) 0.4449(3) 0.0355(14) Uani 1 1 d . . . N18 N 1.1105(3) 0.0927(6) 0.4723(3) 0.0479(13) Uani 1 1 d . . . C19 C 1.1707(4) 0.1411(9) 0.5064(4) 0.062(2) Uani 1 1 d . . . H19A H 1.1696 0.2364 0.5278 0.075 Uiso 1 1 calc R . . C20 C 1.2333(4) 0.0616(11) 0.5122(4) 0.071(2) Uani 1 1 d . . . H20A H 1.2747 0.0985 0.5382 0.085 Uiso 1 1 calc R . . C21 C 1.2352(4) -0.0706(8) 0.4802(3) 0.0513(17) Uani 1 1 d . . . H21A H 1.2788 -0.1276 0.4827 0.062 Uiso 1 1 calc R . . C22 C 1.17578(12) -0.1242(3) 0.44435(11) 0.0284(12) Uani 1 1 d . . . H22A H 1.1767 -0.2163 0.4201 0.034 Uiso 1 1 calc R . . O30 O 0.90874(12) 0.1587(3) 0.40192(11) 0.0321(9) Uani 1 1 d R . . H30A H 0.91478(12) 0.2078(3) 0.44696(11) 0.052(18) Uiso 1 1 d R . . H30B H 0.85724(12) 0.1642(3) 0.38613(11) 0.06(2) Uiso 1 1 d R . . O31 O 0.73617(12) -0.3247(3) 0.14427(11) 0.0336(9) Uani 1 1 d R . . H31A H 0.75682(12) -0.2389(3) 0.16991(11) 0.040 Uiso 1 1 d R . . H31B H 0.74589(12) -0.4129(3) 0.17325(11) 0.040 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 0.0195(4) 0.0219(4) 0.0137(4) 0.0022(2) -0.0040(2) -0.0027(2) N1 0.0184(19) 0.024(2) 0.014(2) 0.0036(16) -0.0042(16) -0.0021(17) C2 0.017(2) 0.019(3) 0.014(2) -0.0012(18) -0.0068(19) -0.0039(19) C3 0.008(2) 0.009(2) 0.007(2) 0.0013(17) -0.0003(15) 0.0011(17) C4 0.020(2) 0.022(3) 0.029(3) -0.002(2) -0.004(2) 0.004(2) C5 0.033(3) 0.024(3) 0.030(3) 0.010(2) -0.002(2) -0.002(2) C6 0.023(3) 0.027(3) 0.029(3) 0.007(2) 0.001(2) 0.002(2) N7 0.020(2) 0.019(2) 0.015(2) 0.0023(16) -0.0012(16) -0.0022(17) O8 0.0233(18) 0.0251(19) 0.0229(18) 0.0023(14) -0.0100(15) 0.0001(14) C8 0.022(3) 0.024(3) 0.011(2) -0.0025(19) 0.0003(19) 0.002(2) C9 0.018(2) 0.027(3) 0.014(2) 0.0004(19) -0.0007(19) 0.000(2) N10 0.022(2) 0.027(2) 0.014(2) 0.0011(17) -0.0006(16) -0.0003(18) C11 0.027(3) 0.023(3) 0.012(2) -0.0005(19) -0.0005(19) 0.004(2) C12 0.035(3) 0.017(3) 0.020(3) 0.0037(19) -0.001(2) 0.001(2) C13 0.031(3) 0.021(3) 0.022(3) -0.001(2) -0.001(2) -0.004(2) C14 0.025(2) 0.025(3) 0.021(3) -0.005(2) -0.004(2) 0.001(2) O15 0.036(2) 0.030(2) 0.0157(18) 0.0032(15) -0.0092(15) 0.0012(16) C15 0.026(3) 0.028(3) 0.015(2) 0.000(2) -0.002(2) 0.004(2) N16 0.024(2) 0.024(2) 0.018(2) 0.0059(17) -0.0080(16) -0.0051(18) C17 0.039(3) 0.052(4) 0.016(3) 0.006(3) -0.001(2) -0.004(3) N18 0.039(3) 0.056(4) 0.048(3) -0.020(3) -0.002(2) -0.004(3) C19 0.043(4) 0.086(6) 0.058(5) -0.036(4) 0.000(3) -0.007(4) C20 0.035(4) 0.115(7) 0.061(5) -0.027(5) -0.010(3) -0.009(4) C21 0.048(4) 0.072(5) 0.033(4) 0.012(3) -0.003(3) 0.006(3) C22 0.026(3) 0.030(3) 0.028(3) 0.002(2) -0.015(2) 0.007(2) O30 0.0279(19) 0.047(2) 0.0215(19) -0.0105(16) -0.0015(15) -0.0009(17) O31 0.044(2) 0.036(2) 0.0200(19) -0.0017(15) -0.0094(16) 0.0033(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N10 1.930(4) . ? Cu1 N1 1.983(4) 2_755 ? Cu1 N16 2.023(4) . ? Cu1 N7 2.048(4) . ? Cu1 O30 2.278(2) . ? N1 C2 1.338(6) . ? N1 C6 1.338(6) . ? N1 Cu1 1.983(4) 2_755 ? C2 C3 1.329(6) . ? C2 N7 1.398(6) . ? C3 C4 1.340(6) . ? C3 H3A 0.9500 . ? C4 C5 1.380(7) . ? C4 H4A 0.9500 . ? C5 C6 1.385(7) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? N7 C8 1.334(6) . ? O8 C8 1.243(5) . ? C8 C9 1.521(6) . ? C9 N10 1.342(6) . ? C9 C14 1.372(7) . ? N10 C11 1.338(6) . ? C11 C12 1.373(7) . ? C11 C15 1.512(7) . ? C12 C13 1.400(7) . ? C12 H12A 0.9500 . ? C13 C14 1.398(7) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? O15 C15 1.252(6) . ? C15 N16 1.324(6) . ? N16 C17 1.425(7) . ? C17 N18 1.314(8) . ? C17 C22 1.327(6) . ? N18 C19 1.331(8) . ? C19 C20 1.352(10) . ? C19 H19A 0.9500 . ? C20 C21 1.337(11) . ? C20 H20A 0.9500 . ? C21 C22 1.350(7) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? O30 H30A 0.9801 . ? O30 H30B 0.9802 . ? O31 H31A 0.9800 . ? O31 H31B 0.9799 . ? 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 N10 Cu1 N1 169.37(16) . 2_755 ? N10 Cu1 N16 79.93(15) . . ? N1 Cu1 N16 97.63(15) 2_755 . ? N10 Cu1 N7 79.13(15) . . ? N1 Cu1 N7 101.26(15) 2_755 . ? N16 Cu1 N7 157.12(15) . . ? N10 Cu1 O30 99.15(13) . . ? N1 Cu1 O30 91.47(12) 2_755 . ? N16 Cu1 O30 106.16(13) . . ? N7 Cu1 O30 86.25(12) . . ? C2 N1 C6 118.0(4) . . ? C2 N1 Cu1 116.5(3) . 2_755 ? C6 N1 Cu1 124.9(3) . 2_755 ? C3 C2 N1 124.8(4) . . ? C3 C2 N7 120.0(4) . . ? N1 C2 N7 115.1(4) . . ? C2 C3 C4 117.0(4) . . ? C2 C3 H3A 121.5 . . ? C4 C3 H3A 121.5 . . ? C3 C4 C5 122.2(4) . . ? C3 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? C4 C5 C6 117.0(4) . . ? C4 C5 H5A 121.5 . . ? C6 C5 H5A 121.5 . . ? N1 C6 C5 121.0(4) . . ? N1 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C8 N7 C2 118.7(4) . . ? C8 N7 Cu1 115.3(3) . . ? C2 N7 Cu1 124.1(3) . . ? O8 C8 N7 128.1(4) . . ? O8 C8 C9 119.6(4) . . ? N7 C8 C9 112.2(4) . . ? N10 C9 C14 120.9(4) . . ? N10 C9 C8 112.2(4) . . ? C14 C9 C8 126.9(4) . . ? C11 N10 C9 121.7(4) . . ? C11 N10 Cu1 118.7(3) . . ? C9 N10 Cu1 119.5(3) . . ? N10 C11 C12 121.1(4) . . ? N10 C11 C15 112.5(4) . . ? C12 C11 C15 126.4(4) . . ? C11 C12 C13 117.9(4) . . ? C11 C12 H12A 121.1 . . ? C13 C12 H12A 121.1 . . ? C14 C13 C12 120.4(5) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C9 C14 C13 118.1(4) . . ? C9 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? O15 C15 N16 128.7(5) . . ? O15 C15 C11 118.2(4) . . ? N16 C15 C11 113.0(4) . . ? C15 N16 C17 117.0(4) . . ? C15 N16 Cu1 115.7(3) . . ? C17 N16 Cu1 127.3(3) . . ? N18 C17 C22 126.6(5) . . ? N18 C17 N16 113.9(5) . . ? C22 C17 N16 119.6(5) . . ? C17 N18 C19 114.7(6) . . ? N18 C19 C20 123.4(7) . . ? N18 C19 H19A 118.3 . . ? C20 C19 H19A 118.3 . . ? C21 C20 C19 118.0(6) . . ? C21 C20 H20A 121.0 . . ? C19 C20 H20A 121.0 . . ? C20 C21 C22 120.9(6) . . ? C20 C21 H21A 119.6 . . ? C22 C21 H21A 119.6 . . ? C17 C22 C21 116.3(4) . . ? C17 C22 H22A 121.9 . . ? C21 C22 H22A 121.9 . . ? Cu1 O30 H30A 132.5 . . ? Cu1 O30 H30B 118.1 . . ? H30A O30 H30B 108.5 . . ? H31A O31 H31B 106.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 1.0(6) . . . . ? Cu1 N1 C2 C3 -169.8(3) 2_755 . . . ? C6 N1 C2 N7 -176.2(4) . . . . ? Cu1 N1 C2 N7 13.0(5) 2_755 . . . ? N1 C2 C3 C4 -0.2(6) . . . . ? N7 C2 C3 C4 176.9(4) . . . . ? C2 C3 C4 C5 -1.4(7) . . . . ? C3 C4 C5 C6 2.0(7) . . . . ? C2 N1 C6 C5 -0.4(7) . . . . ? Cu1 N1 C6 C5 169.7(4) 2_755 . . . ? C4 C5 C6 N1 -1.1(7) . . . . ? C3 C2 N7 C8 61.0(6) . . . . ? N1 C2 N7 C8 -121.7(4) . . . . ? C3 C2 N7 Cu1 -102.2(4) . . . . ? N1 C2 N7 Cu1 75.1(5) . . . . ? N10 Cu1 N7 C8 12.1(3) . . . . ? N1 Cu1 N7 C8 -178.7(3) 2_755 . . . ? N16 Cu1 N7 C8 36.2(6) . . . . ? O30 Cu1 N7 C8 -87.9(3) . . . . ? N10 Cu1 N7 C2 175.9(4) . . . . ? N1 Cu1 N7 C2 -14.9(4) 2_755 . . . ? N16 Cu1 N7 C2 -160.0(4) . . . . ? O30 Cu1 N7 C2 75.8(3) . . . . ? C2 N7 C8 O8 5.5(7) . . . . ? Cu1 N7 C8 O8 170.2(4) . . . . ? C2 N7 C8 C9 -177.7(4) . . . . ? Cu1 N7 C8 C9 -13.0(5) . . . . ? O8 C8 C9 N10 -176.8(4) . . . . ? N7 C8 C9 N10 6.1(5) . . . . ? O8 C8 C9 C14 4.8(7) . . . . ? N7 C8 C9 C14 -172.4(4) . . . . ? C14 C9 N10 C11 -1.1(7) . . . . ? C8 C9 N10 C11 -179.7(4) . . . . ? C14 C9 N10 Cu1 -177.2(3) . . . . ? C8 C9 N10 Cu1 4.2(5) . . . . ? N1 Cu1 N10 C11 82.0(9) 2_755 . . . ? N16 Cu1 N10 C11 4.4(3) . . . . ? N7 Cu1 N10 C11 175.1(4) . . . . ? O30 Cu1 N10 C11 -100.6(3) . . . . ? N1 Cu1 N10 C9 -101.8(8) 2_755 . . . ? N16 Cu1 N10 C9 -179.4(4) . . . . ? N7 Cu1 N10 C9 -8.7(3) . . . . ? O30 Cu1 N10 C9 75.6(3) . . . . ? C9 N10 C11 C12 1.4(7) . . . . ? Cu1 N10 C11 C12 177.5(3) . . . . ? C9 N10 C11 C15 -179.8(4) . . . . ? Cu1 N10 C11 C15 -3.7(5) . . . . ? N10 C11 C12 C13 -0.5(7) . . . . ? C15 C11 C12 C13 -179.1(4) . . . . ? C11 C12 C13 C14 -0.7(7) . . . . ? N10 C9 C14 C13 -0.1(7) . . . . ? C8 C9 C14 C13 178.2(4) . . . . ? C12 C13 C14 C9 1.0(7) . . . . ? N10 C11 C15 O15 177.4(4) . . . . ? C12 C11 C15 O15 -3.9(7) . . . . ? N10 C11 C15 N16 -0.1(6) . . . . ? C12 C11 C15 N16 178.7(4) . . . . ? O15 C15 N16 C17 4.3(8) . . . . ? C11 C15 N16 C17 -178.6(4) . . . . ? O15 C15 N16 Cu1 -173.6(4) . . . . ? C11 C15 N16 Cu1 3.5(5) . . . . ? N10 Cu1 N16 C15 -4.3(3) . . . . ? N1 Cu1 N16 C15 -173.8(3) 2_755 . . . ? N7 Cu1 N16 C15 -28.3(6) . . . . ? O30 Cu1 N16 C15 92.4(3) . . . . ? N10 Cu1 N16 C17 178.1(4) . . . . ? N1 Cu1 N16 C17 8.5(4) 2_755 . . . ? N7 Cu1 N16 C17 154.0(4) . . . . ? O30 Cu1 N16 C17 -85.2(4) . . . . ? C15 N16 C17 N18 -126.4(5) . . . . ? Cu1 N16 C17 N18 51.2(6) . . . . ? C15 N16 C17 C22 54.5(6) . . . . ? Cu1 N16 C17 C22 -127.9(4) . . . . ? C22 C17 N18 C19 -4.8(9) . . . . ? N16 C17 N18 C19 176.2(5) . . . . ? C17 N18 C19 C20 0.9(11) . . . . ? N18 C19 C20 C21 2.0(12) . . . . ? C19 C20 C21 C22 -1.3(11) . . . . ? N18 C17 C22 C21 5.4(7) . . . . ? N16 C17 C22 C21 -175.6(4) . . . . ? C20 C21 C22 C17 -2.1(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O30 H30A O15 0.98 1.79 2.750(4) 166.2 5_756 O30 H30B O31 0.98 1.79 2.768(4) 178.9 4_655 O31 H31A O8 0.98 1.95 2.929(4) 179.8 . O31 H31B O8 0.98 2.65 3.493(4) 144.7 4_645 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.816 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.104 data_7 _database_code_depnum_ccdc_archive 'CCDC 227116' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C68 H44 Cu4 N20 O10.C2 H6 O.2[H2 O]' _chemical_formula_sum 'C70 H54 Cu4 N20 O13' _chemical_formula_weight 1637.49 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.741(3) _cell_length_b 13.793(3) _cell_length_c 20.585(4) _cell_angle_alpha 93.395(4) _cell_angle_beta 92.971(4) _cell_angle_gamma 107.026(3) _cell_volume 3443.8(13) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max .1 _exptl_crystal_size_mid .03 _exptl_crystal_size_min .01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1668 _exptl_absorpt_coefficient_mu 1.299 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.516453 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16877 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 23.31 _reflns_number_total 9502 _reflns_number_gt 8364 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0581P)^2^+192.5971P] 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 RIDING _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00024(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9502 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1385 _refine_ls_R_factor_gt 0.1286 _refine_ls_wR_factor_ref 0.3279 _refine_ls_wR_factor_gt 0.3225 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.30491(14) 0.15224(12) 0.80090(8) 0.0170(4) Uani 1 1 d . . . Cu2 Cu 0.26159(15) 0.25119(13) 0.63627(8) 0.0199(5) Uani 1 1 d . . . Cu3 Cu 0.22498(13) 0.38466(12) 0.87364(8) 0.0165(4) Uani 1 1 d . . . Cu4 Cu 0.27861(14) 0.51790(12) 0.71390(8) 0.0175(4) Uani 1 1 d . . . N1 N 0.3308(9) 0.1078(8) 0.8930(5) 0.017(2) Uiso 1 1 d . . . C2 C 0.2404(12) 0.0424(11) 0.9114(7) 0.020(3) Uiso 1 1 d . . . C3 C 0.2385(15) -0.0091(14) 0.9700(8) 0.038(4) Uiso 1 1 d . . . H3A H 0.1745 -0.0589 0.9812 0.045 Uiso 1 1 calc R . . C4 C 0.3358(13) 0.0182(12) 1.0092(8) 0.030(4) Uiso 1 1 d . . . H4A H 0.3378 -0.0105 1.0499 0.036 Uiso 1 1 calc R . . C5 C 0.4293(14) 0.0860(12) 0.9904(8) 0.031(4) Uiso 1 1 d . . . H5A H 0.4968 0.1031 1.0166 0.037 Uiso 1 1 calc R . . C6 C 0.4217(13) 0.1287(12) 0.9316(7) 0.027(3) Uiso 1 1 d . . . H6A H 0.4860 0.1760 0.9184 0.033 Uiso 1 1 calc R . . C7 C 0.1351(12) 0.0242(11) 0.8676(7) 0.020(3) Uiso 1 1 d . . . O7 O 0.0497(10) -0.0363(9) 0.8808(6) 0.038(3) Uiso 1 1 d . . . N8 N 0.1542(9) 0.0837(8) 0.8173(5) 0.016(2) Uiso 1 1 d . . . C9 C 0.0730(11) 0.0911(10) 0.7728(7) 0.017(3) Uiso 1 1 d . . . N10 N 0.1136(9) 0.1535(8) 0.7245(5) 0.016(2) Uiso 1 1 d . . . O10 O 0.2259(9) 0.1993(8) 0.7272(5) 0.026(2) Uiso 1 1 d . . . C11 C 0.0468(12) 0.1767(11) 0.6751(7) 0.022(3) Uiso 1 1 d . . . C12 C -0.0658(13) 0.1295(11) 0.6749(8) 0.026(3) Uiso 1 1 d . . . H12A H -0.1141 0.1410 0.6415 0.032 Uiso 1 1 calc R . . C13 C -0.1079(13) 0.0663(11) 0.7225(7) 0.024(3) Uiso 1 1 d . . . H13A H -0.1853 0.0366 0.7220 0.028 Uiso 1 1 calc R . . C14 C -0.0405(12) 0.0448(11) 0.7715(7) 0.022(3) Uiso 1 1 d . . . H14A H -0.0710 -0.0005 0.8033 0.026 Uiso 1 1 calc R . . N15 N 0.1054(9) 0.2379(8) 0.6331(5) 0.017(2) Uiso 1 1 d . . . C16 C 0.0617(12) 0.2718(11) 0.5812(7) 0.022(3) Uiso 1 1 d . . . O16 O -0.0361(8) 0.2602(8) 0.5664(5) 0.026(2) Uiso 1 1 d . . . C17 C 0.1482(12) 0.3289(11) 0.5400(7) 0.021(3) Uiso 1 1 d . . . N18 N 0.2529(10) 0.3337(9) 0.5575(6) 0.023(3) Uiso 1 1 d . . . C19 C 0.3328(14) 0.3814(12) 0.5209(8) 0.029(4) Uiso 1 1 d . . . H19A H 0.4064 0.3836 0.5332 0.034 Uiso 1 1 calc R . . C20 C 0.3129(15) 0.4277(13) 0.4658(8) 0.035(4) Uiso 1 1 d . . . H20A H 0.3715 0.4621 0.4410 0.043 Uiso 1 1 calc R . . C21 C 0.2047(14) 0.4225(13) 0.4475(8) 0.033(4) Uiso 1 1 d . . . H21A H 0.1879 0.4524 0.4095 0.040 Uiso 1 1 calc R . . C22 C 0.1211(13) 0.3730(12) 0.4855(8) 0.029(4) Uiso 1 1 d . . . H22A H 0.0468 0.3697 0.4742 0.034 Uiso 1 1 calc R . . N31 N 0.3425(10) 0.0298(9) 0.7405(6) 0.022(3) Uiso 1 1 d . . . C32 C 0.4500(13) 0.0522(12) 0.7369(7) 0.026(3) Uiso 1 1 d . . . C33 C 0.5016(15) -0.0115(13) 0.7061(8) 0.037(4) Uiso 1 1 d . . . H33A H 0.5794 0.0079 0.7053 0.044 Uiso 1 1 calc R . . C34 C 0.4376(17) -0.1032(15) 0.6769(10) 0.048(5) Uiso 1 1 d . . . H34A H 0.4704 -0.1485 0.6553 0.058 Uiso 1 1 calc R . . C35 C 0.3247(16) -0.1287(15) 0.6792(9) 0.046(5) Uiso 1 1 d . . . H35A H 0.2791 -0.1921 0.6596 0.055 Uiso 1 1 calc R . . C36 C 0.2768(14) -0.0592(12) 0.7114(8) 0.029(4) Uiso 1 1 d . . . H36A H 0.1992 -0.0754 0.7123 0.035 Uiso 1 1 calc R . . C37 C 0.5225(12) 0.1561(11) 0.7690(7) 0.023(3) Uiso 1 1 d . . . O37 O 0.6236(9) 0.1747(8) 0.7722(5) 0.034(3) Uiso 1 1 d . . . N38 N 0.4623(10) 0.2138(9) 0.7920(6) 0.019(3) Uiso 1 1 d . . . C39 C 0.5072(11) 0.3099(10) 0.8268(6) 0.016(3) Uiso 1 1 d . . . N40 N 0.4292(9) 0.3504(8) 0.8460(5) 0.017(2) Uiso 1 1 d . . . C41 C 0.4616(11) 0.4432(10) 0.8800(6) 0.016(3) Uiso 1 1 d . . . C42 C 0.5721(12) 0.4946(11) 0.8955(7) 0.023(3) Uiso 1 1 d . . . H42A H 0.5935 0.5594 0.9192 0.028 Uiso 1 1 calc R . . C43 C 0.6500(14) 0.4501(12) 0.8761(8) 0.030(4) Uiso 1 1 d . . . H43A H 0.7259 0.4839 0.8868 0.037 Uiso 1 1 calc R . . C44 C 0.6182(12) 0.3561(11) 0.8408(7) 0.022(3) Uiso 1 1 d . . . H44A H 0.6711 0.3247 0.8267 0.027 Uiso 1 1 calc R . . N45 N 0.3716(9) 0.4762(8) 0.8977(5) 0.017(2) Uiso 1 1 d . . . C46 C 0.3832(12) 0.5662(11) 0.9320(7) 0.021(3) Uiso 1 1 d . . . O46 O 0.4691(9) 0.6318(8) 0.9531(5) 0.029(2) Uiso 1 1 d . . . C47 C 0.2756(12) 0.5850(11) 0.9458(7) 0.022(3) Uiso 1 1 d . . . N48 N 0.1834(10) 0.5179(9) 0.9183(6) 0.022(3) Uiso 1 1 d . . . C49 C 0.0872(14) 0.5366(13) 0.9292(8) 0.032(4) Uiso 1 1 d . . . H49A H 0.0215 0.4881 0.9106 0.039 Uiso 1 1 calc R . . C50 C 0.0769(14) 0.6200(12) 0.9650(8) 0.033(4) Uiso 1 1 d . . . H50A H 0.0076 0.6315 0.9698 0.040 Uiso 1 1 calc R . . C51 C 0.1757(15) 0.6872(14) 0.9943(9) 0.041(4) Uiso 1 1 d . . . H51A H 0.1725 0.7439 1.0218 0.049 Uiso 1 1 calc R . . C52 C 0.2774(14) 0.6740(12) 0.9846(8) 0.029(4) Uiso 1 1 d . . . H52A H 0.3442 0.7214 1.0027 0.035 Uiso 1 1 calc R . . N61 N 0.2146(9) 0.2927(9) 0.9491(5) 0.018(3) Uiso 1 1 d . . . C62 C 0.1098(11) 0.2313(10) 0.9535(7) 0.018(3) Uiso 1 1 d . . . C63 C 0.0808(13) 0.1729(12) 1.0055(7) 0.027(3) Uiso 1 1 d . . . H63A H 0.0078 0.1300 1.0079 0.032 Uiso 1 1 calc R . . C64 C 0.1643(14) 0.1795(12) 1.0552(8) 0.032(4) Uiso 1 1 d . . . H64A H 0.1478 0.1412 1.0922 0.038 Uiso 1 1 calc R . . C65 C 0.2695(13) 0.2416(12) 1.0498(8) 0.029(4) Uiso 1 1 d . . . H65A H 0.3260 0.2490 1.0834 0.035 Uiso 1 1 calc R . . C66 C 0.2902(13) 0.2933(11) 0.9934(7) 0.025(3) Uiso 1 1 d . . . H66A H 0.3639 0.3309 0.9872 0.030 Uiso 1 1 calc R . . C67 C 0.0266(11) 0.2374(10) 0.8996(6) 0.016(3) Uiso 1 1 d . . . O67 O -0.0710(8) 0.1843(7) 0.9001(5) 0.021(2) Uiso 1 1 d . . . N68 N 0.0743(9) 0.3022(8) 0.8554(5) 0.017(2) Uiso 1 1 d . . . C69 C 0.0169(11) 0.3289(10) 0.8046(7) 0.018(3) Uiso 1 1 d . . . N70 N 0.0849(9) 0.3899(8) 0.7638(5) 0.015(2) Uiso 1 1 d . . . O70 O 0.1954(9) 0.4165(8) 0.7778(5) 0.027(2) Uiso 1 1 d . . . C71 C 0.0452(11) 0.4234(10) 0.7090(7) 0.017(3) Uiso 1 1 d . . . C72 C -0.0681(13) 0.3962(11) 0.6949(7) 0.026(3) Uiso 1 1 d . . . H72A H -0.0975 0.4191 0.6574 0.031 Uiso 1 1 calc R . . C73 C -0.1371(14) 0.3363(12) 0.7353(8) 0.029(4) Uiso 1 1 d . . . H73A H -0.2145 0.3177 0.7256 0.034 Uiso 1 1 calc R . . C74 C -0.0958(12) 0.3026(11) 0.7900(7) 0.021(3) Uiso 1 1 d . . . H74A H -0.1447 0.2614 0.8177 0.025 Uiso 1 1 calc R . . N75 N 0.1294(9) 0.4840(8) 0.6765(5) 0.013(2) Uiso 1 1 d . . . C76 C 0.1099(12) 0.5300(11) 0.6231(7) 0.023(3) Uiso 1 1 d . . . O76 O 0.0200(11) 0.5279(10) 0.5963(6) 0.044(3) Uiso 1 1 d . . . C77 C 0.2117(12) 0.5860(11) 0.5934(7) 0.022(3) Uiso 1 1 d . . . N78 N 0.3069(10) 0.5877(9) 0.6265(6) 0.022(3) Uiso 1 1 d . . . C79 C 0.4025(13) 0.6363(12) 0.6042(8) 0.028(4) Uiso 1 1 d . . . H79A H 0.4682 0.6356 0.6280 0.034 Uiso 1 1 calc R . . C80 C 0.4120(13) 0.6882(12) 0.5477(7) 0.027(3) Uiso 1 1 d . . . H80A H 0.4814 0.7227 0.5327 0.033 Uiso 1 1 calc R . . C81 C 0.3106(12) 0.6861(11) 0.5138(7) 0.025(3) Uiso 1 1 d . . . H81A H 0.3121 0.7207 0.4751 0.030 Uiso 1 1 calc R . . C82 C 0.2094(15) 0.6344(13) 0.5362(9) 0.038(4) Uiso 1 1 d . . . H82A H 0.1419 0.6323 0.5134 0.045 Uiso 1 1 calc R . . N91 N 0.2880(10) 0.6537(9) 0.7797(6) 0.022(3) Uiso 1 1 d . . . C92 C 0.3938(12) 0.6985(11) 0.8015(7) 0.022(3) Uiso 1 1 d . . . C93 C 0.4256(14) 0.7909(12) 0.8402(8) 0.030(4) Uiso 1 1 d . . . H93A H 0.5005 0.8218 0.8551 0.036 Uiso 1 1 calc R . . C94 C 0.3460(14) 0.8360(13) 0.8562(8) 0.035(4) Uiso 1 1 d . . . H94A H 0.3655 0.8984 0.8826 0.041 Uiso 1 1 calc R . . C95 C 0.2345(15) 0.7884(13) 0.8329(8) 0.037(4) Uiso 1 1 d . . . H95A H 0.1777 0.8177 0.8424 0.044 Uiso 1 1 calc R . . C96 C 0.2135(14) 0.6974(13) 0.7958(8) 0.032(4) Uiso 1 1 d . . . H96A H 0.1392 0.6638 0.7806 0.039 Uiso 1 1 calc R . . C97 C 0.4762(12) 0.6466(11) 0.7827(7) 0.021(3) Uiso 1 1 d . . . O97 O 0.5750(9) 0.6867(8) 0.8027(5) 0.030(3) Uiso 1 1 d . . . N98 N 0.4336(10) 0.5576(9) 0.7456(6) 0.020(3) Uiso 1 1 d . . . C99 C 0.4997(12) 0.5016(11) 0.7204(7) 0.021(3) Uiso 1 1 d . . . N100 N 0.4375(10) 0.4110(9) 0.6882(6) 0.021(3) Uiso 1 1 d . . . C101 C 0.4913(12) 0.3482(11) 0.6607(7) 0.024(3) Uiso 1 1 d . . . C102 C 0.6041(13) 0.3715(12) 0.6614(8) 0.029(4) Uiso 1 1 d . . . H10A H 0.6392 0.3262 0.6419 0.034 Uiso 1 1 calc R . . C103 C 0.6643(14) 0.4664(12) 0.6928(8) 0.032(4) Uiso 1 1 d . . . H10B H 0.7424 0.4864 0.6937 0.039 Uiso 1 1 calc R . . C104 C 0.6132(14) 0.5316(13) 0.7224(8) 0.031(4) Uiso 1 1 d . . . H10C H 0.6552 0.5953 0.7436 0.037 Uiso 1 1 calc R . . N105 N 0.4148(10) 0.2574(9) 0.6332(6) 0.021(3) Uiso 1 1 d . . . C106 C 0.4441(14) 0.1838(12) 0.6002(8) 0.031(4) Uiso 1 1 d . . . O106 O 0.5367(11) 0.1804(10) 0.5865(7) 0.051(3) Uiso 1 1 d . . . C107 C 0.3397(15) 0.0935(14) 0.5734(9) 0.038(4) Uiso 1 1 d . . . N108 N 0.2427(11) 0.0993(10) 0.5877(7) 0.031(3) Uiso 1 1 d . . . C109 C 0.1530(19) 0.0226(16) 0.5673(10) 0.056(5) Uiso 1 1 d . . . H10D H 0.0822 0.0257 0.5775 0.067 Uiso 1 1 calc R . . C110 C 0.164(2) -0.0631(19) 0.5304(12) 0.067(6) Uiso 1 1 d . . . H11A H 0.1011 -0.1193 0.5180 0.080 Uiso 1 1 calc R . . C111 C 0.257(2) -0.066(2) 0.5137(13) 0.076(7) Uiso 1 1 d . . . H11B H 0.2619 -0.1212 0.4855 0.091 Uiso 1 1 calc R . . C112 C 0.355(2) 0.0107(17) 0.5351(11) 0.061(6) Uiso 1 1 d . . . H11C H 0.4251 0.0071 0.5247 0.073 Uiso 1 1 calc R . . O201 O 0.7178(10) 0.0531(9) 0.8442(6) 0.036(3) Uiso 1 1 d . . . O202 O 0.7250(12) 0.8659(11) 0.7825(7) 0.054(4) Uiso 1 1 d . . . O203 O 0.6515(16) 0.7939(14) 0.6461(9) 0.019(4) Uiso 0.50 1 d P . . H20L H 0.5873 0.7989 0.6453 0.028 Uiso 0.50 1 calc PR . . C203 C 0.711(2) 0.857(2) 0.6043(14) 0.020(6) Uiso 0.50 1 d P . . H20B H 0.7110 0.9273 0.6182 0.023 Uiso 0.50 1 calc PR . . H20C H 0.6709 0.8395 0.5606 0.023 Uiso 0.50 1 calc PR . . C204 C 0.823(2) 0.859(2) 0.5974(14) 0.023(6) Uiso 0.50 1 d P . . H20F H 0.8547 0.9064 0.5652 0.034 Uiso 0.50 1 calc PR . . H20G H 0.8248 0.7904 0.5827 0.034 Uiso 0.50 1 calc PR . . H20H H 0.8653 0.8802 0.6395 0.034 Uiso 0.50 1 calc PR . . O205 O 0.896(3) 0.656(2) 0.8041(15) 0.065(8) Uiso 0.50 1 d P . . H20M H 0.8456 0.6010 0.7958 0.097 Uiso 0.50 1 calc PR . . C205 C 0.913(3) 0.713(3) 0.7446(17) 0.036(8) Uiso 0.50 1 d P . . H20D H 0.9302 0.6707 0.7085 0.043 Uiso 0.50 1 calc PR . . H20E H 0.8452 0.7298 0.7310 0.043 Uiso 0.50 1 calc PR . . C206 C 0.999(3) 0.801(2) 0.7579(15) 0.027(7) Uiso 0.50 1 d P . . H20I H 1.0093 0.8393 0.7190 0.040 Uiso 0.50 1 calc PR . . H20J H 1.0660 0.7835 0.7701 0.040 Uiso 0.50 1 calc PR . . H20K H 0.9815 0.8419 0.7939 0.040 Uiso 0.50 1 calc PR . . 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 0.0184(9) 0.0155(9) 0.0152(9) 0.0015(7) -0.0017(7) 0.0024(7) Cu2 0.0260(10) 0.0166(9) 0.0170(9) 0.0030(7) -0.0013(7) 0.0061(7) Cu3 0.0129(9) 0.0151(9) 0.0193(9) 0.0024(7) -0.0001(7) 0.0009(7) Cu4 0.0188(9) 0.0152(9) 0.0171(9) 0.0030(7) 0.0023(7) 0.0024(7) _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 N8 1.933(11) . ? Cu1 N38 1.958(12) . ? Cu1 O10 2.019(10) . ? Cu1 N1 2.066(11) . ? Cu1 N31 2.217(12) . ? Cu2 N105 1.933(12) . ? Cu2 N15 1.942(12) . ? Cu2 N18 2.052(12) . ? Cu2 O10 2.068(10) . ? Cu2 N108 2.208(14) . ? Cu3 N68 1.928(11) . ? Cu3 N45 1.943(12) . ? Cu3 N61 2.049(11) . ? Cu3 O70 2.085(10) . ? Cu3 N48 2.219(12) . ? Cu4 N75 1.926(11) . ? Cu4 N98 1.953(12) . ? Cu4 O70 2.075(11) . ? Cu4 N78 2.088(12) . ? Cu4 N91 2.216(12) . ? N1 C2 1.327(18) . ? N1 C6 1.318(19) . ? C2 C3 1.43(2) . ? C2 C7 1.52(2) . ? C3 C4 1.38(2) . ? C4 C5 1.37(2) . ? C5 C6 1.39(2) . ? C7 O7 1.217(18) . ? C7 N8 1.348(18) . ? N8 C9 1.375(18) . ? C9 N10 1.375(18) . ? C9 C14 1.40(2) . ? N10 C11 1.403(18) . ? N10 O10 1.381(15) . ? C11 N15 1.344(19) . ? C11 C12 1.39(2) . ? C12 C13 1.37(2) . ? C13 C14 1.39(2) . ? N15 C16 1.348(19) . ? C16 O16 1.228(18) . ? C16 C17 1.49(2) . ? C17 N18 1.344(19) . ? C17 C22 1.38(2) . ? N18 C19 1.34(2) . ? C19 C20 1.38(2) . ? C20 C21 1.39(2) . ? C21 C22 1.39(2) . ? N31 C32 1.32(2) . ? N31 C36 1.35(2) . ? C32 C33 1.39(2) . ? C32 C37 1.55(2) . ? C33 C34 1.37(3) . ? C34 C35 1.38(3) . ? C35 C36 1.43(2) . ? C37 O37 1.234(18) . ? C37 N38 1.340(19) . ? N38 C39 1.414(18) . ? C39 N40 1.340(18) . ? C39 C44 1.38(2) . ? N40 C41 1.361(18) . ? C41 C42 1.39(2) . ? C41 N45 1.409(18) . ? C42 C43 1.37(2) . ? C43 C44 1.39(2) . ? N45 C46 1.356(18) . ? C46 O46 1.236(18) . ? C46 C47 1.51(2) . ? C47 N48 1.338(19) . ? C47 C52 1.42(2) . ? N48 C49 1.35(2) . ? C49 C50 1.37(2) . ? C50 C51 1.41(3) . ? C51 C52 1.38(2) . ? N61 C66 1.289(19) . ? N61 C62 1.366(18) . ? C62 C63 1.38(2) . ? C62 C67 1.518(19) . ? C63 C64 1.42(2) . ? C64 C65 1.38(2) . ? C65 C66 1.40(2) . ? C67 O67 1.246(17) . ? C67 N68 1.353(18) . ? N68 C69 1.373(18) . ? C69 N70 1.378(18) . ? C69 C74 1.39(2) . ? N70 O70 1.358(15) . ? N70 C71 1.372(18) . ? C71 N75 1.383(18) . ? C71 C72 1.39(2) . ? C72 C73 1.37(2) . ? C73 C74 1.38(2) . ? N75 C76 1.347(18) . ? C76 O76 1.239(19) . ? C76 C77 1.48(2) . ? C77 N78 1.355(19) . ? C77 C82 1.39(2) . ? N78 C79 1.33(2) . ? C79 C80 1.39(2) . ? C80 C81 1.43(2) . ? C81 C82 1.40(2) . ? N91 C96 1.31(2) . ? N91 C92 1.347(19) . ? C92 C93 1.40(2) . ? C92 C97 1.49(2) . ? C93 C94 1.38(2) . ? C94 C95 1.42(2) . ? C95 C96 1.38(2) . ? C97 O97 1.253(18) . ? C97 N98 1.357(19) . ? N98 C99 1.397(19) . ? C99 C104 1.38(2) . ? C99 N100 1.378(19) . ? N100 C101 1.367(19) . ? C101 C102 1.38(2) . ? C101 N105 1.408(19) . ? C102 C103 1.41(2) . ? C103 C104 1.39(2) . ? N105 C106 1.34(2) . ? C106 O106 1.24(2) . ? C106 C107 1.58(2) . ? C107 N108 1.31(2) . ? C107 C112 1.41(3) . ? N108 C109 1.34(3) . ? C109 C110 1.41(3) . ? C110 C111 1.26(3) . ? C111 C112 1.40(3) . ? O203 C203 1.36(3) . ? C203 C204 1.44(4) . ? O205 C205 1.49(4) . ? C205 C206 1.37(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Cu1 N38 173.8(5) . . ? N8 Cu1 O10 80.2(4) . . ? N38 Cu1 O10 106.0(5) . . ? N8 Cu1 N1 80.9(5) . . ? N38 Cu1 N1 93.2(5) . . ? O10 Cu1 N1 157.4(4) . . ? N8 Cu1 N31 99.8(5) . . ? N38 Cu1 N31 79.3(5) . . ? O10 Cu1 N31 95.2(4) . . ? N1 Cu1 N31 100.0(4) . . ? N105 Cu2 N15 175.5(5) . . ? N105 Cu2 N18 97.1(5) . . ? N15 Cu2 N18 81.4(5) . . ? N105 Cu2 O10 102.2(5) . . ? N15 Cu2 O10 80.3(4) . . ? N18 Cu2 O10 156.5(5) . . ? N105 Cu2 N108 80.4(5) . . ? N15 Cu2 N108 95.7(5) . . ? N18 Cu2 N108 101.3(5) . . ? O10 Cu2 N108 95.0(5) . . ? N68 Cu3 N45 174.4(5) . . ? N68 Cu3 N61 81.5(5) . . ? N45 Cu3 N61 98.2(5) . . ? N68 Cu3 O70 79.1(4) . . ? N45 Cu3 O70 102.7(4) . . ? N61 Cu3 O70 154.8(4) . . ? N68 Cu3 N48 95.1(5) . . ? N45 Cu3 N48 79.6(5) . . ? N61 Cu3 N48 102.8(4) . . ? O70 Cu3 N48 94.7(4) . . ? N75 Cu4 N98 175.4(5) . . ? N75 Cu4 O70 78.6(4) . . ? N98 Cu4 O70 105.9(5) . . ? N75 Cu4 N78 80.5(5) . . ? N98 Cu4 N78 95.0(5) . . ? O70 Cu4 N78 157.3(5) . . ? N75 Cu4 N91 101.2(4) . . ? N98 Cu4 N91 79.6(5) . . ? O70 Cu4 N91 93.8(4) . . ? N78 Cu4 N91 98.9(5) . . ? C2 N1 C6 118.3(13) . . ? C2 N1 Cu1 111.2(9) . . ? C6 N1 Cu1 130.3(10) . . ? N1 C2 C3 122.8(14) . . ? N1 C2 C7 117.1(12) . . ? C3 C2 C7 120.0(13) . . ? C4 C3 C2 115.9(16) . . ? C5 C4 C3 121.2(16) . . ? C4 C5 C6 117.5(16) . . ? N1 C6 C5 124.2(15) . . ? O7 C7 N8 129.2(14) . . ? O7 C7 C2 120.6(13) . . ? N8 C7 C2 110.2(12) . . ? C7 N8 C9 123.7(12) . . ? C7 N8 Cu1 118.5(9) . . ? C9 N8 Cu1 117.5(9) . . ? N10 C9 N8 112.7(12) . . ? N10 C9 C14 118.6(12) . . ? N8 C9 C14 128.7(13) . . ? C9 N10 C11 123.5(12) . . ? C9 N10 O10 117.6(11) . . ? C11 N10 O10 118.8(11) . . ? N10 O10 Cu1 111.7(7) . . ? N10 O10 Cu2 106.7(7) . . ? Cu1 O10 Cu2 136.8(5) . . ? N15 C11 N10 112.6(12) . . ? N15 C11 C12 130.7(14) . . ? N10 C11 C12 116.6(13) . . ? C13 C12 C11 120.7(14) . . ? C12 C13 C14 121.9(15) . . ? C9 C14 C13 118.6(14) . . ? C11 N15 C16 124.7(12) . . ? C11 N15 Cu2 116.0(9) . . ? C16 N15 Cu2 117.6(9) . . ? O16 C16 N15 127.6(14) . . ? O16 C16 C17 120.6(13) . . ? N15 C16 C17 111.8(12) . . ? N18 C17 C22 121.8(14) . . ? N18 C17 C16 117.1(12) . . ? C22 C17 C16 121.1(13) . . ? C19 N18 C17 119.2(13) . . ? C19 N18 Cu2 129.3(11) . . ? C17 N18 Cu2 111.3(9) . . ? N18 C19 C20 122.7(15) . . ? C21 C20 C19 118.1(16) . . ? C20 C21 C22 119.4(16) . . ? C17 C22 C21 118.7(15) . . ? C32 N31 C36 119.1(13) . . ? C32 N31 Cu1 109.2(10) . . ? C36 N31 Cu1 131.6(10) . . ? N31 C32 C33 124.0(15) . . ? N31 C32 C37 117.8(13) . . ? C33 C32 C37 118.2(14) . . ? C34 C33 C32 118.4(17) . . ? C33 C34 C35 119.1(19) . . ? C34 C35 C36 119.6(18) . . ? N31 C36 C35 119.7(16) . . ? O37 C37 N38 128.8(14) . . ? O37 C37 C32 119.0(13) . . ? N38 C37 C32 112.2(13) . . ? C37 N38 C39 124.1(12) . . ? C37 N38 Cu1 119.6(10) . . ? C39 N38 Cu1 114.1(9) . . ? N40 C39 C44 123.6(13) . . ? N40 C39 N38 112.2(12) . . ? C44 C39 N38 124.2(13) . . ? C39 N40 C41 118.1(12) . . ? N40 C41 C42 121.5(13) . . ? N40 C41 N45 112.3(12) . . ? C42 C41 N45 126.2(13) . . ? C43 C42 C41 118.9(14) . . ? C42 C43 C44 120.2(15) . . ? C39 C44 C43 117.6(14) . . ? C46 N45 C41 123.1(12) . . ? C46 N45 Cu3 119.6(9) . . ? C41 N45 Cu3 117.3(9) . . ? O46 C46 N45 128.5(13) . . ? O46 C46 C47 117.8(13) . . ? N45 C46 C47 113.7(12) . . ? N48 C47 C52 123.7(14) . . ? N48 C47 C46 117.4(13) . . ? C52 C47 C46 118.8(13) . . ? C47 N48 C49 117.3(13) . . ? C47 N48 Cu3 108.8(9) . . ? C49 N48 Cu3 133.3(11) . . ? N48 C49 C50 125.2(16) . . ? C49 C50 C51 115.5(16) . . ? C52 C51 C50 122.6(17) . . ? C51 C52 C47 115.6(15) . . ? C66 N61 C62 119.4(12) . . ? C66 N61 Cu3 128.2(10) . . ? C62 N61 Cu3 112.2(9) . . ? N61 C62 C63 122.1(13) . . ? N61 C62 C67 115.3(12) . . ? C63 C62 C67 122.6(13) . . ? C62 C63 C64 117.2(15) . . ? C65 C64 C63 119.9(15) . . ? C64 C65 C66 117.7(15) . . ? N61 C66 C65 123.5(15) . . ? O67 C67 N68 129.1(12) . . ? O67 C67 C62 119.4(12) . . ? N68 C67 C62 111.5(11) . . ? C67 N68 C69 123.8(12) . . ? C67 N68 Cu3 118.8(9) . . ? C69 N68 Cu3 116.0(9) . . ? N68 C69 N70 112.6(12) . . ? N68 C69 C74 129.2(13) . . ? N70 C69 C74 118.2(12) . . ? O70 N70 C71 118.8(11) . . ? O70 N70 C69 118.7(11) . . ? C71 N70 C69 122.5(12) . . ? N70 O70 Cu4 111.2(8) . . ? N70 O70 Cu3 108.4(7) . . ? Cu4 O70 Cu3 135.9(5) . . ? N70 C71 N75 111.6(12) . . ? N70 C71 C72 118.6(13) . . ? N75 C71 C72 129.8(13) . . ? C73 C72 C71 119.7(14) . . ? C74 C73 C72 120.9(15) . . ? C73 C74 C69 120.1(14) . . ? C76 N75 C71 122.2(12) . . ? C76 N75 Cu4 118.1(9) . . ? C71 N75 Cu4 119.3(9) . . ? O76 C76 N75 128.2(14) . . ? O76 C76 C77 118.4(14) . . ? N75 C76 C77 113.4(13) . . ? N78 C77 C82 122.4(14) . . ? N78 C77 C76 115.0(13) . . ? C82 C77 C76 122.5(14) . . ? C79 N78 C77 119.8(13) . . ? C79 N78 Cu4 128.3(10) . . ? C77 N78 Cu4 111.8(9) . . ? N78 C79 C80 123.7(15) . . ? C79 C80 C81 115.6(15) . . ? C82 C81 C80 121.4(15) . . ? C81 C82 C77 117.1(16) . . ? C96 N91 C92 119.0(13) . . ? C96 N91 Cu4 132.0(11) . . ? C92 N91 Cu4 108.9(9) . . ? N91 C92 C93 121.5(14) . . ? N91 C92 C97 117.6(13) . . ? C93 C92 C97 121.0(14) . . ? C94 C93 C92 118.7(16) . . ? C93 C94 C95 119.5(16) . . ? C96 C95 C94 116.4(16) . . ? N91 C96 C95 125.0(16) . . ? O97 C97 N98 126.9(13) . . ? O97 C97 C92 118.6(13) . . ? N98 C97 C92 114.5(13) . . ? C97 N98 C99 122.3(12) . . ? C97 N98 Cu4 118.8(10) . . ? C99 N98 Cu4 118.1(9) . . ? C104 C99 N100 121.5(13) . . ? C104 C99 N98 126.7(14) . . ? N100 C99 N98 111.6(12) . . ? C101 N100 C99 118.2(12) . . ? N100 C101 C102 124.0(14) . . ? N100 C101 N105 110.1(13) . . ? C102 C101 N105 125.9(14) . . ? C101 C102 C103 115.9(15) . . ? C104 C103 C102 122.0(16) . . ? C99 C104 C103 118.3(15) . . ? C106 N105 C101 123.1(13) . . ? C106 N105 Cu2 120.7(11) . . ? C101 N105 Cu2 115.7(9) . . ? O106 C106 N105 129.7(16) . . ? O106 C106 C107 119.0(15) . . ? N105 C106 C107 111.2(14) . . ? N108 C107 C112 122.9(18) . . ? N108 C107 C106 118.0(15) . . ? C112 C107 C106 119.1(17) . . ? C107 N108 C109 119.3(16) . . ? C107 N108 Cu2 108.9(11) . . ? C109 N108 Cu2 131.4(13) . . ? N108 C109 C110 120(2) . . ? C111 C110 C109 121(3) . . ? C110 C111 C112 122(3) . . ? C111 C112 C107 115(2) . . ? O203 C203 C204 118(2) . . ? C206 C205 O205 109(3) . . ? 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 N8 Cu1 N1 C2 11.2(9) . . . . ? N38 Cu1 N1 C2 -167.0(10) . . . . ? O10 Cu1 N1 C2 44.6(16) . . . . ? N31 Cu1 N1 C2 -87.2(10) . . . . ? N8 Cu1 N1 C6 -174.0(13) . . . . ? N38 Cu1 N1 C6 7.8(13) . . . . ? O10 Cu1 N1 C6 -140.6(13) . . . . ? N31 Cu1 N1 C6 87.6(13) . . . . ? C6 N1 C2 C3 -2(2) . . . . ? Cu1 N1 C2 C3 173.0(12) . . . . ? C6 N1 C2 C7 176.7(13) . . . . ? Cu1 N1 C2 C7 -7.8(15) . . . . ? N1 C2 C3 C4 4(2) . . . . ? C7 C2 C3 C4 -175.1(14) . . . . ? C2 C3 C4 C5 -4(2) . . . . ? C3 C4 C5 C6 2(2) . . . . ? C2 N1 C6 C5 1(2) . . . . ? Cu1 N1 C6 C5 -173.9(11) . . . . ? C4 C5 C6 N1 0(2) . . . . ? N1 C2 C7 O7 178.5(13) . . . . ? C3 C2 C7 O7 -2(2) . . . . ? N1 C2 C7 N8 -2.3(17) . . . . ? C3 C2 C7 N8 176.9(13) . . . . ? O7 C7 N8 C9 5(2) . . . . ? C2 C7 N8 C9 -173.9(12) . . . . ? O7 C7 N8 Cu1 -168.3(13) . . . . ? C2 C7 N8 Cu1 12.6(15) . . . . ? N38 Cu1 N8 C7 4(5) . . . . ? O10 Cu1 N8 C7 178.8(11) . . . . ? N1 Cu1 N8 C7 -13.6(10) . . . . ? N31 Cu1 N8 C7 85.1(10) . . . . ? N38 Cu1 N8 C9 -170(4) . . . . ? O10 Cu1 N8 C9 4.9(9) . . . . ? N1 Cu1 N8 C9 172.5(10) . . . . ? N31 Cu1 N8 C9 -88.8(10) . . . . ? C7 N8 C9 N10 -177.5(12) . . . . ? Cu1 N8 C9 N10 -4.0(15) . . . . ? C7 N8 C9 C14 3(2) . . . . ? Cu1 N8 C9 C14 176.2(12) . . . . ? N8 C9 N10 C11 -177.2(12) . . . . ? C14 C9 N10 C11 3(2) . . . . ? N8 C9 N10 O10 -0.4(16) . . . . ? C14 C9 N10 O10 179.4(12) . . . . ? C9 N10 O10 Cu1 4.2(13) . . . . ? C11 N10 O10 Cu1 -178.8(9) . . . . ? C9 N10 O10 Cu2 164.0(9) . . . . ? C11 N10 O10 Cu2 -19.0(13) . . . . ? N8 Cu1 O10 N10 -4.8(8) . . . . ? N38 Cu1 O10 N10 174.7(8) . . . . ? N1 Cu1 O10 N10 -38.3(15) . . . . ? N31 Cu1 O10 N10 94.3(8) . . . . ? N8 Cu1 O10 Cu2 -155.9(8) . . . . ? N38 Cu1 O10 Cu2 23.5(9) . . . . ? N1 Cu1 O10 Cu2 170.6(8) . . . . ? N31 Cu1 O10 Cu2 -56.9(8) . . . . ? N105 Cu2 O10 N10 -156.2(8) . . . . ? N15 Cu2 O10 N10 20.0(8) . . . . ? N18 Cu2 O10 N10 59.1(14) . . . . ? N108 Cu2 O10 N10 -75.0(8) . . . . ? N105 Cu2 O10 Cu1 -4.1(9) . . . . ? N15 Cu2 O10 Cu1 172.1(8) . . . . ? N18 Cu2 O10 Cu1 -148.9(10) . . . . ? N108 Cu2 O10 Cu1 77.1(8) . . . . ? C9 N10 C11 N15 -179.0(12) . . . . ? O10 N10 C11 N15 4.2(17) . . . . ? C9 N10 C11 C12 -3(2) . . . . ? O10 N10 C11 C12 -179.4(12) . . . . ? N15 C11 C12 C13 177.8(15) . . . . ? N10 C11 C12 C13 2(2) . . . . ? C11 C12 C13 C14 -2(2) . . . . ? N10 C9 C14 C13 -2(2) . . . . ? N8 C9 C14 C13 177.7(13) . . . . ? C12 C13 C14 C9 2(2) . . . . ? N10 C11 N15 C16 -180.0(12) . . . . ? C12 C11 N15 C16 4(2) . . . . ? N10 C11 N15 Cu2 15.0(15) . . . . ? C12 C11 N15 Cu2 -160.8(14) . . . . ? N105 Cu2 N15 C11 104(6) . . . . ? N18 Cu2 N15 C11 174.7(11) . . . . ? O10 Cu2 N15 C11 -20.0(10) . . . . ? N108 Cu2 N15 C11 74.1(10) . . . . ? N105 Cu2 N15 C16 -62(7) . . . . ? N18 Cu2 N15 C16 8.5(10) . . . . ? O10 Cu2 N15 C16 173.8(11) . . . . ? N108 Cu2 N15 C16 -92.1(11) . . . . ? C11 N15 C16 O16 6(2) . . . . ? Cu2 N15 C16 O16 171.1(12) . . . . ? C11 N15 C16 C17 -173.7(13) . . . . ? Cu2 N15 C16 C17 -8.9(15) . . . . ? O16 C16 C17 N18 -176.6(13) . . . . ? N15 C16 C17 N18 3.4(18) . . . . ? O16 C16 C17 C22 2(2) . . . . ? N15 C16 C17 C22 -177.8(13) . . . . ? C22 C17 N18 C19 -1(2) . . . . ? C16 C17 N18 C19 178.0(13) . . . . ? C22 C17 N18 Cu2 -175.7(11) . . . . ? C16 C17 N18 Cu2 3.1(16) . . . . ? N105 Cu2 N18 C19 -4.5(14) . . . . ? N15 Cu2 N18 C19 179.8(13) . . . . ? O10 Cu2 N18 C19 140.9(13) . . . . ? N108 Cu2 N18 C19 -86.0(13) . . . . ? N105 Cu2 N18 C17 169.7(10) . . . . ? N15 Cu2 N18 C17 -6.0(10) . . . . ? O10 Cu2 N18 C17 -44.9(17) . . . . ? N108 Cu2 N18 C17 88.2(10) . . . . ? C17 N18 C19 C20 1(2) . . . . ? Cu2 N18 C19 C20 174.7(12) . . . . ? N18 C19 C20 C21 -1(2) . . . . ? C19 C20 C21 C22 1(2) . . . . ? N18 C17 C22 C21 1(2) . . . . ? C16 C17 C22 C21 -177.8(14) . . . . ? C20 C21 C22 C17 -1(2) . . . . ? N8 Cu1 N31 C32 -165.0(10) . . . . ? N38 Cu1 N31 C32 8.8(10) . . . . ? O10 Cu1 N31 C32 114.1(10) . . . . ? N1 Cu1 N31 C32 -82.6(10) . . . . ? N8 Cu1 N31 C36 12.1(14) . . . . ? N38 Cu1 N31 C36 -174.2(14) . . . . ? O10 Cu1 N31 C36 -68.9(13) . . . . ? N1 Cu1 N31 C36 94.5(13) . . . . ? C36 N31 C32 C33 -2(2) . . . . ? Cu1 N31 C32 C33 175.9(13) . . . . ? C36 N31 C32 C37 178.2(13) . . . . ? Cu1 N31 C32 C37 -4.3(16) . . . . ? N31 C32 C33 C34 1(3) . . . . ? C37 C32 C33 C34 -179.2(15) . . . . ? C32 C33 C34 C35 0(3) . . . . ? C33 C34 C35 C36 1(3) . . . . ? C32 N31 C36 C35 2(2) . . . . ? Cu1 N31 C36 C35 -174.9(12) . . . . ? C34 C35 C36 N31 -2(3) . . . . ? N31 C32 C37 O37 172.8(14) . . . . ? C33 C32 C37 O37 -7(2) . . . . ? N31 C32 C37 N38 -5.3(19) . . . . ? C33 C32 C37 N38 174.5(14) . . . . ? O37 C37 N38 C39 -2(2) . . . . ? C32 C37 N38 C39 176.3(12) . . . . ? O37 C37 N38 Cu1 -163.8(13) . . . . ? C32 C37 N38 Cu1 14.1(16) . . . . ? N8 Cu1 N38 C37 69(5) . . . . ? O10 Cu1 N38 C37 -105.4(11) . . . . ? N1 Cu1 N38 C37 86.6(11) . . . . ? N31 Cu1 N38 C37 -13.0(10) . . . . ? N8 Cu1 N38 C39 -95(4) . . . . ? O10 Cu1 N38 C39 90.6(9) . . . . ? N1 Cu1 N38 C39 -77.3(9) . . . . ? N31 Cu1 N38 C39 -176.9(10) . . . . ? C37 N38 C39 N40 -178.1(12) . . . . ? Cu1 N38 C39 N40 -14.9(14) . . . . ? C37 N38 C39 C44 1(2) . . . . ? Cu1 N38 C39 C44 163.8(11) . . . . ? C44 C39 N40 C41 1(2) . . . . ? N38 C39 N40 C41 -179.9(11) . . . . ? C39 N40 C41 C42 -0.9(19) . . . . ? C39 N40 C41 N45 -179.5(11) . . . . ? N40 C41 C42 C43 0(2) . . . . ? N45 C41 C42 C43 178.1(13) . . . . ? C41 C42 C43 C44 1(2) . . . . ? N40 C39 C44 C43 -1(2) . . . . ? N38 C39 C44 C43 -179.3(13) . . . . ? C42 C43 C44 C39 0(2) . . . . ? N40 C41 N45 C46 179.7(12) . . . . ? C42 C41 N45 C46 1(2) . . . . ? N40 C41 N45 Cu3 2.0(15) . . . . ? C42 C41 N45 Cu3 -176.4(11) . . . . ? N68 Cu3 N45 C46 -10(6) . . . . ? N61 Cu3 N45 C46 -96.3(11) . . . . ? O70 Cu3 N45 C46 97.8(10) . . . . ? N48 Cu3 N45 C46 5.3(10) . . . . ? N68 Cu3 N45 C41 167(5) . . . . ? N61 Cu3 N45 C41 81.4(10) . . . . ? O70 Cu3 N45 C41 -84.4(10) . . . . ? N48 Cu3 N45 C41 -177.0(10) . . . . ? C41 N45 C46 O46 0(2) . . . . ? Cu3 N45 C46 O46 177.5(12) . . . . ? C41 N45 C46 C47 -179.4(12) . . . . ? Cu3 N45 C46 C47 -1.8(16) . . . . ? O46 C46 C47 N48 174.6(13) . . . . ? N45 C46 C47 N48 -6.1(19) . . . . ? O46 C46 C47 C52 -3(2) . . . . ? N45 C46 C47 C52 176.5(13) . . . . ? C52 C47 N48 C49 -1(2) . . . . ? C46 C47 N48 C49 -178.1(13) . . . . ? C52 C47 N48 Cu3 -173.2(12) . . . . ? C46 C47 N48 Cu3 9.6(15) . . . . ? N68 Cu3 N48 C47 170.5(10) . . . . ? N45 Cu3 N48 C47 -8.0(9) . . . . ? N61 Cu3 N48 C47 88.1(10) . . . . ? O70 Cu3 N48 C47 -110.1(10) . . . . ? N68 Cu3 N48 C49 -0.2(14) . . . . ? N45 Cu3 N48 C49 -178.7(14) . . . . ? N61 Cu3 N48 C49 -82.6(14) . . . . ? O70 Cu3 N48 C49 79.3(14) . . . . ? C47 N48 C49 C50 2(2) . . . . ? Cu3 N48 C49 C50 171.6(12) . . . . ? N48 C49 C50 C51 -3(2) . . . . ? C49 C50 C51 C52 4(3) . . . . ? C50 C51 C52 C47 -3(2) . . . . ? N48 C47 C52 C51 2(2) . . . . ? C46 C47 C52 C51 178.9(14) . . . . ? N68 Cu3 N61 C66 179.2(13) . . . . ? N45 Cu3 N61 C66 -6.4(13) . . . . ? O70 Cu3 N61 C66 139.4(12) . . . . ? N48 Cu3 N61 C66 -87.5(13) . . . . ? N68 Cu3 N61 C62 -7.0(9) . . . . ? N45 Cu3 N61 C62 167.4(9) . . . . ? O70 Cu3 N61 C62 -46.9(15) . . . . ? N48 Cu3 N61 C62 86.3(10) . . . . ? C66 N61 C62 C63 3(2) . . . . ? Cu3 N61 C62 C63 -171.4(11) . . . . ? C66 N61 C62 C67 179.1(12) . . . . ? Cu3 N61 C62 C67 4.8(14) . . . . ? N61 C62 C63 C64 1(2) . . . . ? C67 C62 C63 C64 -175.3(13) . . . . ? C62 C63 C64 C65 -1(2) . . . . ? C63 C64 C65 C66 -2(2) . . . . ? C62 N61 C66 C65 -6(2) . . . . ? Cu3 N61 C66 C65 166.9(11) . . . . ? C64 C65 C66 N61 6(2) . . . . ? N61 C62 C67 O67 -179.7(12) . . . . ? C63 C62 C67 O67 -3(2) . . . . ? N61 C62 C67 N68 1.7(17) . . . . ? C63 C62 C67 N68 177.9(13) . . . . ? O67 C67 N68 C69 7(2) . . . . ? C62 C67 N68 C69 -174.3(12) . . . . ? O67 C67 N68 Cu3 173.4(11) . . . . ? C62 C67 N68 Cu3 -8.1(14) . . . . ? N45 Cu3 N68 C67 -78(5) . . . . ? N61 Cu3 N68 C67 8.6(10) . . . . ? O70 Cu3 N68 C67 172.5(10) . . . . ? N48 Cu3 N68 C67 -93.6(10) . . . . ? N45 Cu3 N68 C69 89(5) . . . . ? N61 Cu3 N68 C69 175.8(10) . . . . ? O70 Cu3 N68 C69 -20.3(9) . . . . ? N48 Cu3 N68 C69 73.6(10) . . . . ? C67 N68 C69 N70 -175.5(12) . . . . ? Cu3 N68 C69 N70 18.0(15) . . . . ? C67 N68 C69 C74 4(2) . . . . ? Cu3 N68 C69 C74 -162.3(12) . . . . ? N68 C69 N70 O70 -0.6(17) . . . . ? C74 C69 N70 O70 179.7(12) . . . . ? N68 C69 N70 C71 178.3(12) . . . . ? C74 C69 N70 C71 -1.4(19) . . . . ? C71 N70 O70 Cu4 5.9(13) . . . . ? C69 N70 O70 Cu4 -175.2(9) . . . . ? C71 N70 O70 Cu3 166.2(9) . . . . ? C69 N70 O70 Cu3 -14.9(13) . . . . ? N75 Cu4 O70 N70 -6.0(8) . . . . ? N98 Cu4 O70 N70 174.9(8) . . . . ? N78 Cu4 O70 N70 -29.2(16) . . . . ? N91 Cu4 O70 N70 94.6(8) . . . . ? N75 Cu4 O70 Cu3 -158.6(8) . . . . ? N98 Cu4 O70 Cu3 22.2(9) . . . . ? N78 Cu4 O70 Cu3 178.2(9) . . . . ? N91 Cu4 O70 Cu3 -58.0(8) . . . . ? N68 Cu3 O70 N70 18.4(8) . . . . ? N45 Cu3 O70 N70 -156.2(8) . . . . ? N61 Cu3 O70 N70 58.6(14) . . . . ? N48 Cu3 O70 N70 -75.8(8) . . . . ? N68 Cu3 O70 Cu4 171.6(8) . . . . ? N45 Cu3 O70 Cu4 -3.0(8) . . . . ? N61 Cu3 O70 Cu4 -148.2(8) . . . . ? N48 Cu3 O70 Cu4 77.3(8) . . . . ? O70 N70 C71 N75 -1.6(16) . . . . ? C69 N70 C71 N75 179.5(11) . . . . ? O70 N70 C71 C72 -179.8(12) . . . . ? C69 N70 C71 C72 1.3(19) . . . . ? N70 C71 C72 C73 -1(2) . . . . ? N75 C71 C72 C73 -178.5(14) . . . . ? C71 C72 C73 C74 0(2) . . . . ? C72 C73 C74 C69 0(2) . . . . ? N68 C69 C74 C73 -178.8(14) . . . . ? N70 C69 C74 C73 1(2) . . . . ? N70 C71 N75 C76 -176.4(12) . . . . ? C72 C71 N75 C76 2(2) . . . . ? N70 C71 N75 Cu4 -4.1(15) . . . . ? C72 C71 N75 Cu4 173.9(12) . . . . ? N98 Cu4 N75 C76 -12(6) . . . . ? O70 Cu4 N75 C76 178.3(11) . . . . ? N78 Cu4 N75 C76 -10.6(10) . . . . ? N91 Cu4 N75 C76 86.6(10) . . . . ? N98 Cu4 N75 C71 175(6) . . . . ? O70 Cu4 N75 C71 5.7(9) . . . . ? N78 Cu4 N75 C71 176.8(10) . . . . ? N91 Cu4 N75 C71 -86.0(10) . . . . ? C71 N75 C76 O76 1(2) . . . . ? Cu4 N75 C76 O76 -171.1(13) . . . . ? C71 N75 C76 C77 -176.3(12) . . . . ? Cu4 N75 C76 C77 11.3(16) . . . . ? O76 C76 C77 N78 178.0(14) . . . . ? N75 C76 C77 N78 -4.2(18) . . . . ? O76 C76 C77 C82 -1(2) . . . . ? N75 C76 C77 C82 176.7(14) . . . . ? C82 C77 N78 C79 -1(2) . . . . ? C76 C77 N78 C79 -179.7(13) . . . . ? C82 C77 N78 Cu4 175.1(12) . . . . ? C76 C77 N78 Cu4 -4.0(15) . . . . ? N75 Cu4 N78 C79 -177.1(13) . . . . ? N98 Cu4 N78 C79 2.8(13) . . . . ? O70 Cu4 N78 C79 -154.1(12) . . . . ? N91 Cu4 N78 C79 82.9(13) . . . . ? N75 Cu4 N78 C77 7.7(10) . . . . ? N98 Cu4 N78 C77 -172.5(10) . . . . ? O70 Cu4 N78 C77 30.7(17) . . . . ? N91 Cu4 N78 C77 -92.3(10) . . . . ? C77 N78 C79 C80 1(2) . . . . ? Cu4 N78 C79 C80 -174.0(11) . . . . ? N78 C79 C80 C81 0(2) . . . . ? C79 C80 C81 C82 0(2) . . . . ? C80 C81 C82 C77 1(2) . . . . ? N78 C77 C82 C81 0(2) . . . . ? C76 C77 C82 C81 178.8(14) . . . . ? N75 Cu4 N91 C96 5.8(15) . . . . ? N98 Cu4 N91 C96 -178.8(15) . . . . ? O70 Cu4 N91 C96 -73.3(14) . . . . ? N78 Cu4 N91 C96 87.7(14) . . . . ? N75 Cu4 N91 C92 -169.1(9) . . . . ? N98 Cu4 N91 C92 6.3(9) . . . . ? O70 Cu4 N91 C92 111.8(10) . . . . ? N78 Cu4 N91 C92 -87.2(10) . . . . ? C96 N91 C92 C93 -1(2) . . . . ? Cu4 N91 C92 C93 175.1(12) . . . . ? C96 N91 C92 C97 179.7(13) . . . . ? Cu4 N91 C92 C97 -4.7(15) . . . . ? N91 C92 C93 C94 0(2) . . . . ? C97 C92 C93 C94 179.9(14) . . . . ? C92 C93 C94 C95 0(2) . . . . ? C93 C94 C95 C96 1(2) . . . . ? C92 N91 C96 C95 1(2) . . . . ? Cu4 N91 C96 C95 -173.2(12) . . . . ? C94 C95 C96 N91 -1(3) . . . . ? N91 C92 C97 O97 -179.6(13) . . . . ? C93 C92 C97 O97 1(2) . . . . ? N91 C92 C97 N98 -0.7(19) . . . . ? C93 C92 C97 N98 179.5(13) . . . . ? O97 C97 N98 C99 -5(2) . . . . ? C92 C97 N98 C99 176.3(12) . . . . ? O97 C97 N98 Cu4 -174.3(12) . . . . ? C92 C97 N98 Cu4 6.9(16) . . . . ? N75 Cu4 N98 C97 92(6) . . . . ? O70 Cu4 N98 C97 -98.2(11) . . . . ? N78 Cu4 N98 C97 90.8(11) . . . . ? N91 Cu4 N98 C97 -7.3(10) . . . . ? N75 Cu4 N98 C99 -78(6) . . . . ? O70 Cu4 N98 C99 92.0(10) . . . . ? N78 Cu4 N98 C99 -79.0(10) . . . . ? N91 Cu4 N98 C99 -177.1(11) . . . . ? C97 N98 C99 C104 -8(2) . . . . ? Cu4 N98 C99 C104 161.6(12) . . . . ? C97 N98 C99 N100 175.8(12) . . . . ? Cu4 N98 C99 N100 -14.7(15) . . . . ? C104 C99 N100 C101 3(2) . . . . ? N98 C99 N100 C101 179.8(12) . . . . ? C99 N100 C101 C102 -2(2) . . . . ? C99 N100 C101 N105 176.9(12) . . . . ? N100 C101 C102 C103 0(2) . . . . ? N105 C101 C102 C103 -178.9(14) . . . . ? C101 C102 C103 C104 1(2) . . . . ? N100 C99 C104 C103 -2(2) . . . . ? N98 C99 C104 C103 -178.0(14) . . . . ? C102 C103 C104 C99 0(2) . . . . ? N100 C101 N105 C106 176.7(13) . . . . ? C102 C101 N105 C106 -4(2) . . . . ? N100 C101 N105 Cu2 4.1(15) . . . . ? C102 C101 N105 Cu2 -176.8(12) . . . . ? N15 Cu2 N105 C106 -23(7) . . . . ? N18 Cu2 N105 C106 -92.5(12) . . . . ? O10 Cu2 N105 C106 100.8(12) . . . . ? N108 Cu2 N105 C106 7.7(12) . . . . ? N15 Cu2 N105 C101 150(6) . . . . ? N18 Cu2 N105 C101 80.3(10) . . . . ? O10 Cu2 N105 C101 -86.4(10) . . . . ? N108 Cu2 N105 C101 -179.5(11) . . . . ? C101 N105 C106 O106 -2(3) . . . . ? Cu2 N105 C106 O106 170.6(15) . . . . ? C101 N105 C106 C107 -178.1(13) . . . . ? Cu2 N105 C106 C107 -5.8(18) . . . . ? O106 C106 C107 N108 -179.0(16) . . . . ? N105 C106 C107 N108 -2(2) . . . . ? O106 C106 C107 C112 1(3) . . . . ? N105 C106 C107 C112 177.5(17) . . . . ? C112 C107 N108 C109 2(3) . . . . ? C106 C107 N108 C109 -178.1(16) . . . . ? C112 C107 N108 Cu2 -172.2(16) . . . . ? C106 C107 N108 Cu2 7.5(18) . . . . ? N105 Cu2 N108 C107 -8.1(11) . . . . ? N15 Cu2 N108 C107 169.6(11) . . . . ? N18 Cu2 N108 C107 87.3(12) . . . . ? O10 Cu2 N108 C107 -109.7(11) . . . . ? N105 Cu2 N108 C109 178.4(17) . . . . ? N15 Cu2 N108 C109 -3.9(17) . . . . ? N18 Cu2 N108 C109 -86.2(17) . . . . ? O10 Cu2 N108 C109 76.8(17) . . . . ? C107 N108 C109 C110 0(3) . . . . ? Cu2 N108 C109 C110 172.6(15) . . . . ? N108 C109 C110 C111 -4(4) . . . . ? C109 C110 C111 C112 6(4) . . . . ? C110 C111 C112 C107 -4(4) . . . . ? N108 C107 C112 C111 0(3) . . . . ? C106 C107 C112 C111 179.9(18) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 2.714 _refine_diff_density_min -1.331 _refine_diff_density_rms 0.245 data_H2L10 _database_code_depnum_ccdc_archive 'CCDC 227117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 N5 O2.H2 O' _chemical_formula_sum 'C21 H23 N5 O3' _chemical_formula_weight 393.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.140(3) _cell_length_b 9.5051(11) _cell_length_c 13.026(5) _cell_angle_alpha 81.99(6) _cell_angle_beta 81.50(7) _cell_angle_gamma 63.11(5) _cell_volume 994.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1460 _cell_measurement_theta_min 3.442 _cell_measurement_theta_max 74.4988 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .15 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.740 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.2920 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8241 _diffrn_reflns_av_R_equivalents 0.0732 _diffrn_reflns_av_sigmaI/netI 0.0860 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.11 _diffrn_reflns_theta_max 73.31 _reflns_number_total 3520 _reflns_number_gt 2401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0753P)^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 0.0135(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3520 _refine_ls_number_parameters 279 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1492 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.003 _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 1.3937(2) -0.2831(2) 0.68539(15) 0.0468(5) Uani 1 1 d . . . C2 C 1.2299(2) -0.1957(2) 0.69688(16) 0.0366(5) Uani 1 1 d . . . C3 C 1.1356(3) -0.2184(3) 0.78515(18) 0.0449(6) Uani 1 1 d . . . H3A H 1.0224 -0.1549 0.7924 0.054 Uiso 1 1 calc R . . C4 C 1.2083(3) -0.3341(3) 0.86179(18) 0.0474(6) Uani 1 1 d . . . H4A H 1.1461 -0.3488 0.9219 0.057 Uiso 1 1 calc R . . C5 C 1.3751(3) -0.4280(3) 0.84778(18) 0.0474(6) Uani 1 1 d . . . H5A H 1.4281 -0.5099 0.8971 0.057 Uiso 1 1 calc R . . C6 C 1.4614(3) -0.3979(3) 0.75927(18) 0.0498(6) Uani 1 1 d . . . H6A H 1.5743 -0.4617 0.7502 0.060 Uiso 1 1 calc R . . C7 C 1.1530(3) -0.0702(3) 0.61162(19) 0.0476(6) Uani 1 1 d . . . H7A H 1.0367 -0.0438 0.6154 0.057 Uiso 1 1 calc R . . H7B H 1.2040 -0.1117 0.5448 0.057 Uiso 1 1 calc R . . C8 C 1.1716(3) 0.0792(3) 0.61850(18) 0.0465(6) Uani 1 1 d . . . H8A H 1.1279 0.1163 0.6873 0.056 Uiso 1 1 calc R . . H8B H 1.2877 0.0544 0.6094 0.056 Uiso 1 1 calc R . . N9 N 1.0868(2) 0.2046(2) 0.54066(14) 0.0421(5) Uani 1 1 d D . . H9N H 1.143(3) 0.218(3) 0.4727(11) 0.073(9) Uiso 1 1 d D . . C10 C 0.9304(3) 0.3100(3) 0.55902(17) 0.0405(5) Uani 1 1 d . . . O10 O 0.8472(2) 0.3108(2) 0.64329(13) 0.0633(5) Uani 1 1 d . . . C11 C 0.8559(2) 0.4312(2) 0.47208(15) 0.0352(5) Uani 1 1 d . . . N12 N 0.95104(19) 0.42604(19) 0.38254(12) 0.0336(4) Uani 1 1 d . . . C13 C 0.8838(2) 0.5355(2) 0.30524(15) 0.0355(5) Uani 1 1 d . . . C14 C 0.7217(2) 0.6514(3) 0.31355(18) 0.0456(6) Uani 1 1 d . . . H14A H 0.6792 0.7252 0.2578 0.055 Uiso 1 1 calc R . . C15 C 0.6259(3) 0.6549(3) 0.40537(19) 0.0534(7) Uani 1 1 d . . . H15A H 0.5172 0.7318 0.4133 0.064 Uiso 1 1 calc R . . C16 C 0.6927(3) 0.5430(3) 0.48574(18) 0.0472(6) Uani 1 1 d . . . H16A H 0.6294 0.5423 0.5485 0.057 Uiso 1 1 calc R . . C17 C 0.9892(3) 0.5283(2) 0.20428(16) 0.0397(5) Uani 1 1 d . . . O17 O 0.9390(2) 0.6296(2) 0.13186(13) 0.0670(6) Uani 1 1 d . . . N18 N 1.1362(2) 0.4020(2) 0.19671(13) 0.0403(5) Uani 1 1 d D . . H18N H 1.180(3) 0.330(3) 0.2578(13) 0.067(8) Uiso 1 1 d D . . C19 C 1.2402(3) 0.3804(3) 0.09852(17) 0.0459(6) Uani 1 1 d . . . H19A H 1.2852 0.4568 0.0884 0.055 Uiso 1 1 calc R . . H19B H 1.1734 0.4009 0.0419 0.055 Uiso 1 1 calc R . . C20 C 1.3805(3) 0.2154(3) 0.0946(2) 0.0506(6) Uani 1 1 d . . . H20A H 1.4495 0.2104 0.0297 0.061 Uiso 1 1 calc R . . H20B H 1.4473 0.1958 0.1511 0.061 Uiso 1 1 calc R . . C21 C 1.3258(2) 0.0871(2) 0.10267(17) 0.0413(5) Uani 1 1 d . . . N22 N 1.3502(2) -0.0074(2) 0.19041(15) 0.0485(5) Uani 1 1 d . . . C23 C 1.3031(3) -0.1224(3) 0.2002(2) 0.0551(7) Uani 1 1 d . . . H23A H 1.3209 -0.1883 0.2615 0.066 Uiso 1 1 calc R . . C24 C 1.2303(3) -0.1499(3) 0.1260(2) 0.0597(7) Uani 1 1 d . . . H24A H 1.1981 -0.2311 0.1367 0.072 Uiso 1 1 calc R . . C25 C 1.2063(3) -0.0535(3) 0.0350(2) 0.0610(8) Uani 1 1 d . . . H25A H 1.1588 -0.0694 -0.0180 0.073 Uiso 1 1 calc R . . C26 C 1.2535(3) 0.0677(3) 0.02319(19) 0.0532(7) Uani 1 1 d . . . H26A H 1.2367 0.1352 -0.0375 0.064 Uiso 1 1 calc R . . O30 O 1.3572(2) 0.1369(3) 0.37072(14) 0.0692(6) Uani 1 1 d D . . H30A H 1.449(4) 0.166(5) 0.362(3) 0.141(16) Uiso 1 1 d D . . H30B H 1.383(5) 0.070(4) 0.314(2) 0.115(13) Uiso 1 1 d 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 N1 0.0426(9) 0.0478(11) 0.0420(10) 0.0005(9) 0.0009(8) -0.0157(9) C2 0.0443(11) 0.0310(10) 0.0363(11) -0.0019(9) -0.0037(9) -0.0185(9) C3 0.0372(10) 0.0389(11) 0.0515(13) -0.0010(10) 0.0040(10) -0.0138(9) C4 0.0532(12) 0.0461(13) 0.0444(13) 0.0006(10) 0.0049(10) -0.0272(11) C5 0.0564(13) 0.0409(12) 0.0435(13) 0.0084(10) -0.0111(10) -0.0216(10) C6 0.0406(11) 0.0467(13) 0.0507(14) 0.0016(11) -0.0033(10) -0.0110(10) C7 0.0536(12) 0.0425(12) 0.0467(13) 0.0015(10) -0.0097(10) -0.0211(10) C8 0.0545(12) 0.0405(12) 0.0428(12) 0.0070(10) -0.0101(10) -0.0207(10) N9 0.0452(9) 0.0392(10) 0.0371(10) 0.0090(8) -0.0030(8) -0.0179(8) C10 0.0448(11) 0.0424(12) 0.0378(11) 0.0021(9) 0.0015(9) -0.0253(10) O10 0.0614(10) 0.0677(12) 0.0465(10) 0.0100(8) 0.0130(8) -0.0255(9) C11 0.0378(10) 0.0335(10) 0.0358(11) -0.0047(9) 0.0025(8) -0.0184(9) N12 0.0350(8) 0.0310(8) 0.0334(9) -0.0004(7) -0.0019(7) -0.0142(7) C13 0.0387(10) 0.0316(10) 0.0340(11) -0.0026(8) -0.0043(8) -0.0134(8) C14 0.0420(11) 0.0396(12) 0.0446(13) -0.0027(10) -0.0122(9) -0.0067(9) C15 0.0353(10) 0.0543(14) 0.0532(14) -0.0107(12) 0.0001(10) -0.0041(10) C16 0.0381(11) 0.0555(14) 0.0446(13) -0.0097(11) 0.0047(10) -0.0185(10) C17 0.0469(11) 0.0338(11) 0.0331(11) 0.0012(9) -0.0065(9) -0.0135(9) O17 0.0762(11) 0.0516(10) 0.0410(9) 0.0129(8) -0.0019(8) -0.0057(9) N18 0.0429(9) 0.0380(10) 0.0313(9) 0.0031(8) 0.0034(7) -0.0138(8) C19 0.0530(12) 0.0407(12) 0.0398(12) -0.0023(10) 0.0120(10) -0.0221(10) C20 0.0453(11) 0.0461(13) 0.0535(14) -0.0031(11) 0.0143(10) -0.0199(10) C21 0.0342(9) 0.0338(11) 0.0442(12) -0.0045(9) 0.0108(9) -0.0087(8) N22 0.0446(9) 0.0459(11) 0.0517(12) 0.0041(9) 0.0003(8) -0.0208(9) C23 0.0490(12) 0.0481(14) 0.0636(16) 0.0128(12) -0.0042(12) -0.0225(11) C24 0.0453(12) 0.0473(14) 0.086(2) -0.0130(14) 0.0051(13) -0.0215(11) C25 0.0480(13) 0.0622(17) 0.0668(18) -0.0271(15) -0.0048(12) -0.0132(12) C26 0.0485(12) 0.0470(14) 0.0440(13) -0.0013(11) -0.0013(10) -0.0050(11) O30 0.0578(10) 0.0882(15) 0.0580(12) -0.0143(11) 0.0102(9) -0.0315(10) _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 C6 1.331(3) . ? N1 C2 1.341(3) . ? C2 C3 1.385(3) . ? C2 C7 1.501(3) . ? C3 C4 1.370(3) . ? C4 C5 1.374(3) . ? C5 C6 1.370(3) . ? C7 C8 1.521(3) . ? C8 N9 1.452(3) . ? N9 C10 1.332(3) . ? C10 O10 1.238(3) . ? C10 C11 1.493(3) . ? C11 N12 1.340(3) . ? C11 C16 1.388(3) . ? N12 C13 1.337(3) . ? C13 C14 1.389(3) . ? C13 C17 1.501(3) . ? C14 C15 1.369(3) . ? C15 C16 1.375(4) . ? C17 O17 1.226(3) . ? C17 N18 1.338(3) . ? N18 C19 1.456(3) . ? C19 C20 1.513(3) . ? C20 C21 1.500(3) . ? C21 N22 1.331(3) . ? C21 C26 1.381(4) . ? N22 C23 1.330(3) . ? C23 C24 1.364(4) . ? C24 C25 1.373(4) . ? C25 C26 1.385(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 117.66(19) . . ? N1 C2 C3 121.1(2) . . ? N1 C2 C7 117.60(19) . . ? C3 C2 C7 121.25(19) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C5 118.5(2) . . ? C6 C5 C4 118.3(2) . . ? N1 C6 C5 124.1(2) . . ? C2 C7 C8 112.5(2) . . ? N9 C8 C7 112.4(2) . . ? C10 N9 C8 121.90(19) . . ? O10 C10 N9 123.2(2) . . ? O10 C10 C11 120.0(2) . . ? N9 C10 C11 116.86(18) . . ? N12 C11 C16 122.5(2) . . ? N12 C11 C10 117.78(18) . . ? C16 C11 C10 119.71(19) . . ? C13 N12 C11 117.44(17) . . ? N12 C13 C14 123.20(19) . . ? N12 C13 C17 117.53(17) . . ? C14 C13 C17 119.3(2) . . ? C15 C14 C13 118.7(2) . . ? C14 C15 C16 119.0(2) . . ? C15 C16 C11 119.2(2) . . ? O17 C17 N18 122.49(19) . . ? O17 C17 C13 121.20(18) . . ? N18 C17 C13 116.23(19) . . ? C17 N18 C19 119.46(19) . . ? N18 C19 C20 112.53(19) . . ? C21 C20 C19 114.00(18) . . ? N22 C21 C26 121.5(2) . . ? N22 C21 C20 116.6(2) . . ? C26 C21 C20 121.8(2) . . ? C23 N22 C21 118.2(2) . . ? N22 C23 C24 124.3(3) . . ? C23 C24 C25 117.6(3) . . ? C24 C25 C26 119.2(3) . . ? C21 C26 C25 119.1(3) . . ? 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 C6 N1 C2 C3 3.3(3) . . . . ? C6 N1 C2 C7 -177.8(2) . . . . ? N1 C2 C3 C4 -1.5(3) . . . . ? C7 C2 C3 C4 179.7(2) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? C3 C4 C5 C6 2.1(4) . . . . ? C2 N1 C6 C5 -2.6(4) . . . . ? C4 C5 C6 N1 -0.1(4) . . . . ? N1 C2 C7 C8 -79.8(2) . . . . ? C3 C2 C7 C8 99.0(3) . . . . ? C2 C7 C8 N9 -175.77(17) . . . . ? C7 C8 N9 C10 89.9(3) . . . . ? C8 N9 C10 O10 1.3(4) . . . . ? C8 N9 C10 C11 -178.8(2) . . . . ? O10 C10 C11 N12 179.7(2) . . . . ? N9 C10 C11 N12 -0.3(3) . . . . ? O10 C10 C11 C16 -0.9(3) . . . . ? N9 C10 C11 C16 179.2(2) . . . . ? C16 C11 N12 C13 0.9(3) . . . . ? C10 C11 N12 C13 -179.64(19) . . . . ? C11 N12 C13 C14 -0.5(3) . . . . ? C11 N12 C13 C17 -178.98(18) . . . . ? N12 C13 C14 C15 0.4(3) . . . . ? C17 C13 C14 C15 178.8(2) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C15 C16 C11 0.9(4) . . . . ? N12 C11 C16 C15 -1.1(3) . . . . ? C10 C11 C16 C15 179.5(2) . . . . ? N12 C13 C17 O17 -176.0(2) . . . . ? C14 C13 C17 O17 5.5(3) . . . . ? N12 C13 C17 N18 7.1(3) . . . . ? C14 C13 C17 N18 -171.4(2) . . . . ? O17 C17 N18 C19 -1.5(4) . . . . ? C13 C17 N18 C19 175.35(19) . . . . ? C17 N18 C19 C20 -166.0(2) . . . . ? N18 C19 C20 C21 62.4(3) . . . . ? C19 C20 C21 N22 -110.0(2) . . . . ? C19 C20 C21 C26 70.0(3) . . . . ? C26 C21 N22 C23 0.0(3) . . . . ? C20 C21 N22 C23 179.98(18) . . . . ? C21 N22 C23 C24 -0.3(3) . . . . ? N22 C23 C24 C25 0.8(3) . . . . ? C23 C24 C25 C26 -1.1(3) . . . . ? N22 C21 C26 C25 -0.4(3) . . . . ? C20 C21 C26 C25 179.68(18) . . . . ? C24 C25 C26 C21 0.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N9 H9N O30 0.979(5) 2.082(15) 2.961(3) 148(2) . N18 H18N O30 0.977(5) 2.328(10) 3.275(4) 163(2) . O30 H30B N22 0.979(5) 1.969(15) 2.902(3) 159(3) . O30 H30A N1 0.981(5) 2.166(14) 3.120(3) 164(4) 2_856 _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 73.31 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 0.185 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.047 data_H2L12 _database_code_depnum_ccdc_archive 'CCDC 227118' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N4 O2' _chemical_formula_sum 'C19 H16 N4 O2' _chemical_formula_weight 332.36 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.893(5) _cell_length_b 9.1295(18) _cell_length_c 16.445(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.623(3) _cell_angle_gamma 90.00 _cell_volume 3369.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 71 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.725780 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6961 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 23.33 _reflns_number_total 2386 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0640P)^2^+0.4333P] 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 0.0030(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2386 _refine_ls_number_parameters 246 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.41785(6) 0.38249(16) 0.23016(9) 0.0332(4) Uani 1 1 d . . . C2 C 0.37034(7) 0.46019(18) 0.22219(11) 0.0294(4) Uani 1 1 d . . . C3 C 0.36328(7) 0.5151(2) 0.29523(12) 0.0383(5) Uani 1 1 d . . . H3A H 0.3293 0.5718 0.2867 0.046 Uiso 1 1 calc R . . C4 C 0.40664(8) 0.4859(2) 0.38094(12) 0.0421(5) Uani 1 1 d . . . H4A H 0.4029 0.5216 0.4325 0.051 Uiso 1 1 calc R . . C5 C 0.45520(7) 0.4043(2) 0.39020(12) 0.0362(4) Uani 1 1 d . . . H5A H 0.4854 0.3811 0.4484 0.043 Uiso 1 1 calc R . . C6 C 0.45950(7) 0.35669(19) 0.31399(11) 0.0338(4) Uani 1 1 d . . . H6A H 0.4938 0.3025 0.3211 0.041 Uiso 1 1 calc R . . C7 C 0.32210(7) 0.48151(18) 0.12857(11) 0.0302(4) Uani 1 1 d . . . O7 O 0.27745(5) 0.55368(13) 0.11466(8) 0.0384(3) Uani 1 1 d . . . N8 N 0.33267(6) 0.41273(15) 0.06416(9) 0.0310(4) Uani 1 1 d D . . H8 H 0.3702(4) 0.3587(16) 0.0846(10) 0.037(5) Uiso 1 1 d D . . C9 C 0.29308(7) 0.4056(2) -0.02865(11) 0.0326(4) Uani 1 1 d . . . C10 C 0.29059(7) 0.27742(19) -0.07664(10) 0.0316(4) Uani 1 1 d . . . C11 C 0.25078(7) 0.2691(2) -0.16775(11) 0.0417(5) Uani 1 1 d . . . H11A H 0.2494 0.1827 -0.2009 0.050 Uiso 1 1 calc R . . C12 C 0.21303(7) 0.3857(3) -0.21081(13) 0.0509(6) Uani 1 1 d . . . C13 C 0.21607(9) 0.5128(3) -0.16260(14) 0.0548(6) Uani 1 1 d . . . C14 C 0.25633(8) 0.5221(2) -0.07298(12) 0.0461(5) Uani 1 1 d . . . H14A H 0.2589 0.6104 -0.0409 0.055 Uiso 1 1 calc R . . N15 N 0.32485(6) 0.15087(16) -0.03502(8) 0.0301(4) Uani 1 1 d D . . H15 H 0.3040(8) 0.0567(10) -0.0460(12) 0.050(6) Uiso 1 1 d D . . C16 C 0.38467(7) 0.14640(18) 0.01005(10) 0.0277(4) Uani 1 1 d . . . O16 O 0.41646(5) 0.25560(13) 0.02393(7) 0.0349(3) Uani 1 1 d . . . C17 C 0.41080(7) -0.00076(19) 0.04448(10) 0.0313(4) Uani 1 1 d . . . N18 N 0.37283(7) -0.11003(18) 0.03047(12) 0.0501(5) Uani 1 1 d . . . C19 C 0.39572(11) -0.2413(2) 0.06255(17) 0.0656(7) Uani 1 1 d . . . H19A H 0.3689 -0.3207 0.0525 0.079 Uiso 1 1 calc R . . C20 C 0.45468(11) -0.2684(2) 0.10841(15) 0.0618(6) Uani 1 1 d . . . H20A H 0.4688 -0.3635 0.1312 0.074 Uiso 1 1 calc R . . C21 C 0.49321(10) -0.1557(3) 0.12095(16) 0.0656(7) Uani 1 1 d . . . H21A H 0.5350 -0.1716 0.1517 0.079 Uiso 1 1 calc R . . C22 C 0.47133(8) -0.0184(2) 0.08888(13) 0.0487(5) Uani 1 1 d . . . H22A H 0.4975 0.0618 0.0973 0.058 Uiso 1 1 calc R . . C23A C 0.16923(12) 0.3878(3) -0.30465(16) 0.0423(7) Uani 0.65 1 d P . . H23A H 0.1882 0.3573 -0.3432 0.063 Uiso 0.65 1 calc PR . . H23B H 0.1533 0.4871 -0.3211 0.063 Uiso 0.65 1 calc PR . . H23C H 0.1367 0.3203 -0.3128 0.063 Uiso 0.65 1 calc PR . . C23B C 0.1671(3) 0.5986(6) -0.2200(4) 0.0470(14) Uani 0.35 1 d P . . H23D H 0.1312 0.5674 -0.2142 0.070 Uiso 0.35 1 calc PR . . H23E H 0.1609 0.5860 -0.2826 0.070 Uiso 0.35 1 calc PR . . H23F H 0.1751 0.7020 -0.2030 0.070 Uiso 0.35 1 calc PR . . 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 0.0283(7) 0.0390(9) 0.0346(8) 0.0043(7) 0.0157(7) 0.0054(7) C2 0.0227(8) 0.0271(9) 0.0386(9) -0.0009(8) 0.0134(7) -0.0021(7) C3 0.0252(9) 0.0411(11) 0.0476(11) -0.0149(9) 0.0147(8) 0.0015(8) C4 0.0316(10) 0.0547(13) 0.0392(10) -0.0176(9) 0.0147(8) -0.0010(9) C5 0.0263(9) 0.0455(11) 0.0353(9) -0.0079(8) 0.0121(7) -0.0015(8) C6 0.0265(9) 0.0432(11) 0.0335(10) 0.0020(8) 0.0146(8) 0.0063(8) C7 0.0246(9) 0.0264(9) 0.0421(10) 0.0025(8) 0.0168(7) 0.0000(8) O7 0.0256(7) 0.0405(7) 0.0462(7) -0.0033(6) 0.0128(5) 0.0046(6) N8 0.0264(8) 0.0337(8) 0.0328(8) 0.0070(6) 0.0127(6) 0.0067(6) C9 0.0241(9) 0.0444(11) 0.0321(9) 0.0136(8) 0.0147(7) 0.0054(8) C10 0.0199(8) 0.0451(11) 0.0285(9) 0.0108(8) 0.0092(7) -0.0032(8) C11 0.0276(9) 0.0662(14) 0.0297(10) 0.0103(9) 0.0108(8) -0.0147(9) C12 0.0217(9) 0.0913(17) 0.0345(10) 0.0326(12) 0.0074(8) -0.0031(10) C13 0.0399(11) 0.0844(17) 0.0474(12) 0.0346(12) 0.0259(10) 0.0215(11) C14 0.0416(11) 0.0584(13) 0.0461(12) 0.0254(10) 0.0263(9) 0.0208(10) N15 0.0257(8) 0.0360(9) 0.0264(7) 0.0030(6) 0.0092(6) -0.0048(6) C16 0.0272(9) 0.0334(10) 0.0236(8) -0.0001(7) 0.0121(7) -0.0047(8) O16 0.0255(6) 0.0372(7) 0.0394(7) 0.0043(5) 0.0115(5) -0.0033(5) C17 0.0335(9) 0.0359(10) 0.0267(9) -0.0013(7) 0.0151(7) -0.0004(8) N18 0.0495(10) 0.0353(10) 0.0669(11) 0.0071(8) 0.0263(9) -0.0041(8) C19 0.0731(16) 0.0396(13) 0.0963(18) 0.0178(12) 0.0482(14) 0.0052(12) C20 0.0835(17) 0.0402(13) 0.0686(15) 0.0164(11) 0.0393(13) 0.0211(13) C21 0.0536(14) 0.0583(16) 0.0710(15) 0.0054(12) 0.0140(12) 0.0206(12) C22 0.0402(11) 0.0394(12) 0.0567(12) 0.0017(10) 0.0116(9) 0.0056(9) C23A 0.0381(15) 0.0559(19) 0.0248(14) 0.0062(13) 0.0059(12) -0.0141(14) C23B 0.066(4) 0.044(3) 0.045(3) 0.015(3) 0.036(3) 0.023(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 C2 1.336(2) . ? N1 C6 1.340(2) . ? C2 C3 1.381(2) . ? C2 C7 1.500(2) . ? C3 C4 1.381(3) . ? C3 H3A 0.9500 . ? C4 C5 1.371(2) . ? C4 H4A 0.9500 . ? C5 C6 1.374(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 O7 1.2254(19) . ? C7 N8 1.352(2) . ? N8 C9 1.416(2) . ? N8 H8 0.9797(11) . ? C9 C14 1.386(2) . ? C9 C10 1.398(3) . ? C10 C11 1.396(2) . ? C10 N15 1.423(2) . ? C11 C12 1.394(3) . ? C11 H11A 0.9500 . ? C12 C13 1.389(3) . ? C12 C23A 1.454(3) . ? C13 C14 1.381(3) . ? C13 C23B 1.413(6) . ? C14 H14A 0.9500 . ? N15 C16 1.347(2) . ? N15 H15 0.9797(11) . ? C16 O16 1.2313(19) . ? C16 C17 1.493(2) . ? C17 N18 1.324(2) . ? C17 C22 1.370(3) . ? N18 C19 1.334(3) . ? C19 C20 1.352(3) . ? C19 H19A 0.9500 . ? C20 C21 1.360(3) . ? C20 H20A 0.9500 . ? C21 C22 1.377(3) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 116.91(14) . . ? N1 C2 C3 123.19(15) . . ? N1 C2 C7 116.83(14) . . ? C3 C2 C7 119.93(14) . . ? C4 C3 C2 118.71(16) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 118.74(16) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 118.90(16) . . ? C4 C5 H5A 120.5 . . ? C6 C5 H5A 120.5 . . ? N1 C6 C5 123.52(15) . . ? N1 C6 H6A 118.2 . . ? C5 C6 H6A 118.2 . . ? O7 C7 N8 124.87(15) . . ? O7 C7 C2 121.34(15) . . ? N8 C7 C2 113.78(14) . . ? C7 N8 C9 125.85(14) . . ? C7 N8 H8 116.5(10) . . ? C9 N8 H8 117.6(10) . . ? C14 C9 C10 119.15(16) . . ? C14 C9 N8 121.68(17) . . ? C10 C9 N8 119.17(15) . . ? C11 C10 C9 119.30(16) . . ? C11 C10 N15 118.13(16) . . ? C9 C10 N15 122.48(14) . . ? C12 C11 C10 120.9(2) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C13 C12 C11 119.33(17) . . ? C13 C12 C23A 115.2(2) . . ? C11 C12 C23A 125.5(2) . . ? C14 C13 C12 119.74(19) . . ? C14 C13 C23B 134.2(3) . . ? C12 C13 C23B 105.3(3) . . ? C13 C14 C9 121.6(2) . . ? C13 C14 H14A 119.2 . . ? C9 C14 H14A 119.2 . . ? C16 N15 C10 125.41(14) . . ? C16 N15 H15 116.5(11) . . ? C10 N15 H15 117.7(11) . . ? O16 C16 N15 123.12(15) . . ? O16 C16 C17 121.23(14) . . ? N15 C16 C17 115.64(14) . . ? N18 C17 C22 122.80(17) . . ? N18 C17 C16 116.78(15) . . ? C22 C17 C16 120.42(16) . . ? C17 N18 C19 117.21(18) . . ? N18 C19 C20 124.1(2) . . ? N18 C19 H19A 118.0 . . ? C20 C19 H19A 118.0 . . ? C19 C20 C21 118.0(2) . . ? C19 C20 H20A 121.0 . . ? C21 C20 H20A 121.0 . . ? C20 C21 C22 119.6(2) . . ? C20 C21 H21A 120.2 . . ? C22 C21 H21A 120.2 . . ? C17 C22 C21 118.2(2) . . ? C17 C22 H22A 120.9 . . ? C21 C22 H22A 120.9 . . ? C12 C23A H23A 109.5 . . ? C12 C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C12 C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C13 C23B H23D 109.5 . . ? C13 C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C13 C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 0.9(2) . . . . ? C6 N1 C2 C7 -176.54(14) . . . . ? N1 C2 C3 C4 -1.5(3) . . . . ? C7 C2 C3 C4 175.92(16) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C2 N1 C6 C5 0.7(3) . . . . ? C4 C5 C6 N1 -1.7(3) . . . . ? N1 C2 C7 O7 -178.54(14) . . . . ? C3 C2 C7 O7 3.9(2) . . . . ? N1 C2 C7 N8 2.5(2) . . . . ? C3 C2 C7 N8 -175.11(15) . . . . ? O7 C7 N8 C9 -3.6(3) . . . . ? C2 C7 N8 C9 175.34(14) . . . . ? C7 N8 C9 C14 35.8(2) . . . . ? C7 N8 C9 C10 -143.62(16) . . . . ? C14 C9 C10 C11 -0.6(2) . . . . ? N8 C9 C10 C11 178.79(14) . . . . ? C14 C9 C10 N15 -177.04(14) . . . . ? N8 C9 C10 N15 2.4(2) . . . . ? C9 C10 C11 C12 -1.0(2) . . . . ? N15 C10 C11 C12 175.54(14) . . . . ? C10 C11 C12 C13 1.3(2) . . . . ? C10 C11 C12 C23A -178.80(19) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C23A C12 C13 C14 -179.85(19) . . . . ? C11 C12 C13 C23B -171.3(3) . . . . ? C23A C12 C13 C23B 8.8(3) . . . . ? C12 C13 C14 C9 -1.7(3) . . . . ? C23B C13 C14 C9 166.6(4) . . . . ? C10 C9 C14 C13 2.0(3) . . . . ? N8 C9 C14 C13 -177.39(16) . . . . ? C11 C10 N15 C16 125.62(16) . . . . ? C9 C10 N15 C16 -57.9(2) . . . . ? C10 N15 C16 O16 3.7(2) . . . . ? C10 N15 C16 C17 -177.43(13) . . . . ? O16 C16 C17 N18 176.37(15) . . . . ? N15 C16 C17 N18 -2.5(2) . . . . ? O16 C16 C17 C22 -3.1(2) . . . . ? N15 C16 C17 C22 178.02(15) . . . . ? C22 C17 N18 C19 0.7(3) . . . . ? C16 C17 N18 C19 -178.71(17) . . . . ? C17 N18 C19 C20 0.4(3) . . . . ? N18 C19 C20 C21 -1.5(4) . . . . ? C19 C20 C21 C22 1.5(4) . . . . ? N18 C17 C22 C21 -0.7(3) . . . . ? C16 C17 C22 C21 178.70(17) . . . . ? C20 C21 C22 C17 -0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 O16 0.9797(11) 2.048(12) 2.8355(18) 135.9(13) . N15 H15 O7 0.9797(11) 2.103(11) 2.9672(18) 146.1(16) 7 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 23.33 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.216 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.038 data_h2l8 _database_code_depnum_ccdc_archive 'CCDC 227119' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 N5 O2. H2 O' _chemical_formula_sum 'C17 H15 N5 O3' _chemical_formula_weight 337.34 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.8239(4) _cell_length_b 16.5567(17) _cell_length_c 24.639(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1560.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 68 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .13 _exptl_crystal_size_mid .01 _exptl_crystal_size_min .01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.918445 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7616 _diffrn_reflns_av_R_equivalents 0.1445 _diffrn_reflns_av_sigmaI/netI 0.1504 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 23.31 _reflns_number_total 2161 _reflns_number_gt 973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(7) _refine_ls_number_reflns 2161 _refine_ls_number_parameters 224 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1898 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1707 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.003 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 0.504(2) 1.1416(4) 0.4749(3) 0.049(2) Uani 1 1 d . . . C2 C 0.404(3) 1.0719(5) 0.4524(3) 0.037(2) Uani 1 1 d . . . C3 C 0.422(2) 1.0575(5) 0.3983(3) 0.042(3) Uani 1 1 d . . . H3A H 0.3641 1.0070 0.3846 0.051 Uiso 1 1 calc R . . C4 C 0.527(3) 1.1179(6) 0.3641(4) 0.058(3) Uani 1 1 d . . . H4A H 0.5266 1.1102 0.3267 0.069 Uiso 1 1 calc R . . C5 C 0.630(3) 1.1885(5) 0.3856(3) 0.037(3) Uani 1 1 d . . . H5A H 0.7124 1.2295 0.3632 0.044 Uiso 1 1 calc R . . C6 C 0.613(3) 1.2002(5) 0.4408(4) 0.050(3) Uani 1 1 d . . . H6A H 0.6780 1.2500 0.4551 0.060 Uiso 1 1 calc R . . N7 N 0.2828(18) 1.0169(3) 0.4927(2) 0.0376(19) Uani 1 1 d D . . H7N H 0.3081 1.0353 0.5303 0.045 Uiso 1 1 calc RD . . C8 C 0.137(2) 0.9426(5) 0.4864(3) 0.034(2) Uani 1 1 d . . . O8 O 0.0865(17) 0.9103(3) 0.4411(2) 0.0636(19) Uani 1 1 d . . . C9 C 0.033(2) 0.9015(5) 0.5370(3) 0.035(3) Uani 1 1 d . . . N10 N 0.1149(14) 0.9390(3) 0.5834(3) 0.0389(15) Uani 1 1 d . . . C11 C 0.025(2) 0.9012(5) 0.6302(3) 0.028(2) Uani 1 1 d . . . C12 C -0.149(3) 0.8295(5) 0.6320(3) 0.039(3) Uani 1 1 d . . . H12A H -0.2119 0.8062 0.6650 0.047 Uiso 1 1 calc R . . C13 C -0.2299(19) 0.7925(3) 0.5833(4) 0.0420(19) Uani 1 1 d . . . H13A H -0.3444 0.7430 0.5829 0.050 Uiso 1 1 calc R . . C14 C -0.141(2) 0.8290(5) 0.5369(3) 0.034(3) Uani 1 1 d . . . H14A H -0.1979 0.8048 0.5040 0.041 Uiso 1 1 calc R . . C15 C 0.136(3) 0.9422(5) 0.6824(3) 0.047(3) Uani 1 1 d . . . O15 O 0.1065(18) 0.9067(3) 0.7260(2) 0.0617(18) Uani 1 1 d . . . N16 N 0.271(2) 1.0154(4) 0.6759(2) 0.053(2) Uani 1 1 d D . . H16N H 0.2799 1.0353 0.6385 0.063 Uiso 1 1 calc RD . . C17 C 0.407(3) 1.0697(5) 0.7165(3) 0.039(2) Uani 1 1 d . . . N18 N 0.490(2) 1.1425(4) 0.6968(3) 0.051(3) Uani 1 1 d . . . C19 C 0.623(3) 1.1957(5) 0.7317(4) 0.057(3) Uani 1 1 d . . . H19A H 0.6936 1.2456 0.7183 0.069 Uiso 1 1 calc R . . C20 C 0.662(3) 1.1810(6) 0.7876(4) 0.057(4) Uani 1 1 d . . . H20A H 0.7439 1.2202 0.8114 0.069 Uiso 1 1 calc R . . C21 C 0.572(3) 1.1051(6) 0.8043(3) 0.049(3) Uani 1 1 d . . . H21A H 0.6005 1.0919 0.8407 0.059 Uiso 1 1 calc R . . C22 C 0.4415(13) 1.0472(2) 0.7695(2) 0.048(3) Uani 1 1 d . . . H22A H 0.3807 0.9958 0.7815 0.058 Uiso 1 1 calc R . . O30 O 0.7385(13) 1.1095(2) 0.5857(2) 0.091(2) Uani 1 1 d RD . . H30A H 0.6260(13) 1.1555(2) 0.5678(2) 0.109 Uiso 1 1 d RD . . H30B H 0.7178(13) 1.1167(2) 0.6251(2) 0.109 Uiso 1 1 d RD . . 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 0.063(7) 0.044(4) 0.040(4) 0.004(4) -0.010(4) -0.014(5) C2 0.044(7) 0.034(5) 0.032(5) -0.002(4) 0.000(5) 0.011(4) C3 0.055(6) 0.031(4) 0.041(6) -0.008(4) 0.012(4) -0.002(5) C4 0.085(10) 0.064(7) 0.023(5) -0.011(4) 0.004(5) 0.003(7) C5 0.040(7) 0.043(5) 0.028(5) 0.018(4) 0.010(5) 0.004(5) C6 0.057(8) 0.043(5) 0.051(6) 0.003(4) 0.015(6) -0.024(6) N7 0.051(5) 0.037(4) 0.024(4) -0.008(3) 0.006(3) -0.008(4) C8 0.035(6) 0.041(5) 0.026(4) -0.003(4) 0.002(4) -0.001(5) O8 0.095(5) 0.055(4) 0.041(3) -0.009(3) -0.001(3) -0.004(4) C9 0.037(7) 0.025(5) 0.043(6) -0.008(4) -0.007(5) 0.009(5) N10 0.043(4) 0.022(3) 0.052(4) -0.012(4) 0.008(6) 0.004(3) C11 0.027(6) 0.034(5) 0.023(5) -0.010(4) 0.000(4) -0.001(5) C12 0.053(7) 0.033(5) 0.032(5) 0.005(4) 0.007(5) 0.004(5) C13 0.052(5) 0.027(3) 0.048(4) 0.000(5) 0.008(6) 0.003(3) C14 0.030(7) 0.033(5) 0.038(5) -0.014(4) -0.008(5) 0.008(5) C15 0.062(7) 0.035(5) 0.044(6) 0.001(4) -0.001(5) 0.006(6) O15 0.088(5) 0.055(3) 0.042(4) 0.007(3) -0.010(3) -0.024(4) N16 0.081(6) 0.043(5) 0.034(5) 0.000(3) 0.010(4) 0.000(5) C17 0.036(6) 0.035(5) 0.046(6) -0.013(4) -0.005(5) -0.004(5) N18 0.072(8) 0.042(5) 0.038(4) -0.006(4) -0.008(4) 0.001(5) C19 0.053(8) 0.044(6) 0.075(7) 0.005(5) -0.006(7) -0.009(6) C20 0.055(9) 0.059(7) 0.058(7) -0.027(5) 0.001(7) -0.013(6) C21 0.048(7) 0.070(7) 0.029(5) -0.017(5) 0.010(5) 0.004(6) C22 0.038(6) 0.052(6) 0.054(6) 0.005(5) 0.015(5) -0.011(5) O30 0.145(6) 0.062(3) 0.065(3) 0.005(4) -0.016(6) 0.021(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 C2 1.335(10) . ? N1 C6 1.349(10) . ? C2 C3 1.357(10) . ? C2 N7 1.424(9) . ? C3 C4 1.367(10) . ? C4 C5 1.343(11) . ? C5 C6 1.376(9) . ? N7 C8 1.361(9) . ? C8 O8 1.252(7) . ? C8 C9 1.475(10) . ? C9 N10 1.337(9) . ? C9 C14 1.373(11) . ? N10 C11 1.356(9) . ? C11 C12 1.361(11) . ? C11 C15 1.514(10) . ? C12 C13 1.383(10) . ? C13 C14 1.337(10) . ? C15 O15 1.231(8) . ? C15 N16 1.327(10) . ? N16 C17 1.441(10) . ? C17 N18 1.339(10) . ? C17 C22 1.364(10) . ? N18 C19 1.332(11) . ? C19 C20 1.406(12) . ? C20 C21 1.367(12) . ? C21 C22 1.380(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 C2 N1 C6 116.8(8) . . ? N1 C2 C3 123.1(9) . . ? N1 C2 N7 110.9(7) . . ? C3 C2 N7 126.0(8) . . ? C2 C3 C4 119.5(8) . . ? C5 C4 C3 118.6(8) . . ? C4 C5 C6 119.9(10) . . ? N1 C6 C5 122.0(10) . . ? C8 N7 C2 129.3(6) . . ? O8 C8 N7 123.4(7) . . ? O8 C8 C9 121.1(7) . . ? N7 C8 C9 115.6(7) . . ? N10 C9 C14 121.4(8) . . ? N10 C9 C8 116.5(7) . . ? C14 C9 C8 122.1(8) . . ? C9 N10 C11 117.0(5) . . ? N10 C11 C12 123.6(7) . . ? N10 C11 C15 116.3(8) . . ? C12 C11 C15 120.0(8) . . ? C11 C12 C13 117.8(7) . . ? C14 C13 C12 119.1(6) . . ? C13 C14 C9 121.1(7) . . ? O15 C15 N16 125.2(7) . . ? O15 C15 C11 120.0(8) . . ? N16 C15 C11 114.7(7) . . ? C15 N16 C17 128.8(7) . . ? N18 C17 C22 124.8(7) . . ? N18 C17 N16 113.2(7) . . ? C22 C17 N16 122.0(7) . . ? C19 N18 C17 116.8(7) . . ? N18 C19 C20 124.0(9) . . ? C21 C20 C19 115.4(9) . . ? C20 C21 C22 122.9(8) . . ? C17 C22 C21 116.1(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 C3 2.7(17) . . . . ? C6 N1 C2 N7 -177.6(8) . . . . ? N1 C2 C3 C4 -4.0(18) . . . . ? N7 C2 C3 C4 176.3(8) . . . . ? C2 C3 C4 C5 4.1(16) . . . . ? C3 C4 C5 C6 -3.1(19) . . . . ? C2 N1 C6 C5 -1.7(18) . . . . ? C4 C5 C6 N1 2(2) . . . . ? N1 C2 N7 C8 174.8(8) . . . . ? C3 C2 N7 C8 -5.5(17) . . . . ? C2 N7 C8 O8 0.1(14) . . . . ? C2 N7 C8 C9 -179.0(8) . . . . ? O8 C8 C9 N10 176.4(7) . . . . ? N7 C8 C9 N10 -4.4(11) . . . . ? O8 C8 C9 C14 -4.0(13) . . . . ? N7 C8 C9 C14 175.1(8) . . . . ? C14 C9 N10 C11 1.4(10) . . . . ? C8 C9 N10 C11 -179.1(8) . . . . ? C9 N10 C11 C12 -1.8(11) . . . . ? C9 N10 C11 C15 177.0(8) . . . . ? N10 C11 C12 C13 1.8(13) . . . . ? C15 C11 C12 C13 -177.0(7) . . . . ? C11 C12 C13 C14 -1.4(11) . . . . ? C12 C13 C14 C9 1.0(11) . . . . ? N10 C9 C14 C13 -1.0(14) . . . . ? C8 C9 C14 C13 179.4(8) . . . . ? N10 C11 C15 O15 -170.1(8) . . . . ? C12 C11 C15 O15 8.7(13) . . . . ? N10 C11 C15 N16 7.8(11) . . . . ? C12 C11 C15 N16 -173.4(9) . . . . ? O15 C15 N16 C17 -0.9(16) . . . . ? C11 C15 N16 C17 -178.7(9) . . . . ? C15 N16 C17 N18 -173.4(9) . . . . ? C15 N16 C17 C22 6.3(15) . . . . ? C22 C17 N18 C19 1.3(16) . . . . ? N16 C17 N18 C19 -179.0(8) . . . . ? C17 N18 C19 C20 -3.3(18) . . . . ? N18 C19 C20 C21 4(2) . . . . ? C19 C20 C21 C22 -1.9(18) . . . . ? N18 C17 C22 C21 0.1(14) . . . . ? N16 C17 C22 C21 -179.5(8) . . . . ? C20 C21 C22 C17 0.2(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7N N10 0.98 2.19 2.661(10) 107.8 . N7 H7N O30 0.98 2.47 3.262(8) 138.1 . N16 H16N N10 0.98 2.19 2.675(10) 109.2 . N16 H16N O30 0.98 2.50 3.249(9) 132.6 . O30 H30A N1 0.98 2.35 2.922(9) 116.7 . O30 H30B N18 0.98 2.02 2.947(8) 158.1 . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 23.31 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.271 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.051 data_H2L9 _database_code_depnum_ccdc_archive 'CCDC 227120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N5 O2' _chemical_formula_sum 'C19 H17 N5 O2' _chemical_formula_weight 347.38 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 Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 16.3620(10) _cell_length_b 14.3991(9) _cell_length_c 14.4267(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.2660(10) _cell_angle_gamma 90.00 _cell_volume 3398.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 54 _cell_measurement_theta_min 12 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type MULTISCAN _exptl_absorpt_correction_T_min 0.799522 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7218 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 23.30 _reflns_number_total 2432 _reflns_number_gt 2006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0530P)^2^+0.7197P] 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 0.0114(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2432 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 N1 N 0.65247(7) 0.26350(9) 0.06177(9) 0.0592(4) Uani 1 1 d . . . C2 C 0.57876(8) 0.27705(10) 0.09776(10) 0.0502(4) Uani 1 1 d . . . C3 C 0.55967(10) 0.24588(12) 0.18495(12) 0.0658(5) Uani 1 1 d . . . H3A H 0.5091 0.2593 0.2098 0.079 Uiso 1 1 calc R . . C4 C 0.61655(12) 0.19457(14) 0.23479(13) 0.0825(5) Uani 1 1 d . . . H4A H 0.6043 0.1712 0.2929 0.099 Uiso 1 1 calc R . . C5 C 0.69134(11) 0.17847(14) 0.19744(14) 0.0784(5) Uani 1 1 d . . . H5A H 0.7304 0.1428 0.2289 0.094 Uiso 1 1 calc R . . C6 C 0.70721(10) 0.21583(13) 0.11320(13) 0.0688(5) Uani 1 1 d . . . H6A H 0.7593 0.2078 0.0898 0.083 Uiso 1 1 calc R . . C7 C 0.51959(9) 0.32702(11) 0.03425(11) 0.0592(4) Uani 1 1 d . . . H7A H 0.5402 0.3892 0.0236 0.071 Uiso 1 1 calc R . . H7B H 0.5178 0.2951 -0.0250 0.071 Uiso 1 1 calc R . . N8 N 0.43682(7) 0.33422(8) 0.06778(9) 0.0533(3) Uani 1 1 d D . . H8N H 0.3987(7) 0.2823(7) 0.0594(11) 0.066(4) Uiso 1 1 d D . . C9 C 0.40758(9) 0.41361(10) 0.10159(10) 0.0541(4) Uani 1 1 d . . . O9 O 0.44936(7) 0.48310(8) 0.11703(9) 0.0800(4) Uani 1 1 d . . . C10 C 0.31692(8) 0.41491(9) 0.11642(10) 0.0493(4) Uani 1 1 d . . . N11 N 0.27803(6) 0.33339(8) 0.11934(7) 0.0463(3) Uani 1 1 d . . . C12 C 0.19683(8) 0.33468(10) 0.12997(9) 0.0480(4) Uani 1 1 d . . . C13 C 0.15230(10) 0.41605(12) 0.13527(11) 0.0601(4) Uani 1 1 d . . . H13A H 0.0959 0.4145 0.1416 0.072 Uiso 1 1 calc R . . C14 C 0.19299(11) 0.49906(12) 0.13104(13) 0.0710(5) Uani 1 1 d . . . H14A H 0.1645 0.5548 0.1342 0.085 Uiso 1 1 calc R . . C15 C 0.27634(11) 0.49911(11) 0.12202(12) 0.0661(5) Uani 1 1 d . . . H15A H 0.3051 0.5547 0.1197 0.079 Uiso 1 1 calc R . . C16 C 0.15400(8) 0.24266(10) 0.13360(10) 0.0520(4) Uani 1 1 d . . . O16 O 0.08137(6) 0.23776(8) 0.15373(9) 0.0736(4) Uani 1 1 d . . . N17 N 0.19950(7) 0.16934(8) 0.11309(9) 0.0567(3) Uani 1 1 d D . . H17N H 0.2561(4) 0.1795(11) 0.0948(12) 0.077(5) Uiso 1 1 d D . . C18 C 0.16595(10) 0.07655(11) 0.10709(11) 0.0631(4) Uani 1 1 d . . . H18A H 0.1232 0.0707 0.1523 0.076 Uiso 1 1 calc R . . H18B H 0.2086 0.0325 0.1238 0.076 Uiso 1 1 calc R . . C19 C 0.13091(8) 0.05051(10) 0.01269(10) 0.0512(4) Uani 1 1 d . . . N20 N 0.12770(8) 0.11493(8) -0.05365(9) 0.0604(4) Uani 1 1 d . . . C21 C 0.09635(10) 0.08906(12) -0.13643(12) 0.0674(5) Uani 1 1 d . . . H21A H 0.0942 0.1333 -0.1834 0.081 Uiso 1 1 calc R . . C22 C 0.06739(10) 0.00219(12) -0.15630(12) 0.0689(5) Uani 1 1 d . . . H22A H 0.0463 -0.0122 -0.2150 0.083 Uiso 1 1 calc R . . C23 C 0.07033(11) -0.06310(12) -0.08737(13) 0.0721(5) Uani 1 1 d . . . H23A H 0.0511 -0.1230 -0.0982 0.087 Uiso 1 1 calc R . . C24 C 0.10220(10) -0.03860(10) -0.00199(12) 0.0642(4) Uani 1 1 d . . . H24A H 0.1045 -0.0819 0.0458 0.077 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0478(7) 0.0628(8) 0.0671(9) -0.0064(6) 0.0043(6) -0.0033(6) C2 0.0443(8) 0.0483(8) 0.0582(9) -0.0074(7) 0.0033(7) -0.0079(6) C3 0.0541(9) 0.0821(12) 0.0614(10) 0.0007(8) 0.0046(8) -0.0041(8) C4 0.0769(12) 0.1081(15) 0.0623(11) 0.0121(10) -0.0080(9) -0.0027(11) C5 0.0670(11) 0.0889(13) 0.0785(13) 0.0007(10) -0.0178(9) 0.0048(9) C6 0.0477(9) 0.0778(12) 0.0806(13) -0.0113(10) -0.0040(8) 0.0036(8) C7 0.0487(8) 0.0650(10) 0.0641(10) 0.0058(8) 0.0073(7) -0.0020(7) N8 0.0436(7) 0.0487(7) 0.0676(8) -0.0018(6) 0.0028(6) -0.0016(5) C9 0.0575(9) 0.0491(9) 0.0556(9) -0.0009(7) -0.0006(7) -0.0085(7) O9 0.0741(8) 0.0610(7) 0.1051(10) -0.0151(6) 0.0077(7) -0.0221(6) C10 0.0561(9) 0.0435(8) 0.0482(8) -0.0070(6) -0.0014(6) -0.0003(7) N11 0.0463(7) 0.0474(7) 0.0452(7) -0.0057(5) 0.0007(5) 0.0006(5) C12 0.0465(8) 0.0566(9) 0.0407(7) -0.0075(6) 0.0011(6) 0.0055(6) C13 0.0534(9) 0.0697(11) 0.0569(9) -0.0117(8) -0.0015(7) 0.0153(8) C14 0.0741(12) 0.0547(10) 0.0838(12) -0.0121(9) -0.0037(9) 0.0203(9) C15 0.0743(12) 0.0453(9) 0.0787(11) -0.0097(8) -0.0012(9) 0.0031(8) C16 0.0447(8) 0.0652(10) 0.0462(8) -0.0019(7) 0.0029(6) -0.0019(7) O16 0.0474(7) 0.0899(9) 0.0840(8) 0.0000(6) 0.0162(6) -0.0042(5) N17 0.0497(7) 0.0513(8) 0.0695(8) -0.0060(6) 0.0077(6) -0.0073(6) C18 0.0649(10) 0.0539(9) 0.0705(11) 0.0067(8) 0.0005(8) -0.0138(7) C19 0.0443(8) 0.0436(8) 0.0658(10) 0.0037(7) 0.0058(7) -0.0043(6) N20 0.0699(9) 0.0493(7) 0.0621(9) 0.0047(7) 0.0067(6) -0.0104(6) C21 0.0749(11) 0.0636(11) 0.0640(11) 0.0091(8) 0.0063(8) -0.0058(8) C22 0.0679(11) 0.0724(12) 0.0664(11) -0.0068(9) 0.0020(8) -0.0109(9) C23 0.0756(11) 0.0536(10) 0.0872(13) -0.0083(9) 0.0009(9) -0.0148(8) C24 0.0693(10) 0.0446(9) 0.0786(12) 0.0092(8) -0.0013(9) -0.0070(7) _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 C2 1.3379(17) . ? N1 C6 1.340(2) . ? C2 C3 1.378(2) . ? C2 C7 1.502(2) . ? C3 C4 1.378(2) . ? C4 C5 1.368(3) . ? C5 C6 1.359(3) . ? C7 N8 1.4518(18) . ? N8 C9 1.3356(19) . ? C9 O9 1.2294(18) . ? C9 C10 1.504(2) . ? C10 N11 1.3362(17) . ? C10 C15 1.385(2) . ? N11 C12 1.3410(17) . ? C12 C13 1.383(2) . ? C12 C16 1.500(2) . ? C13 C14 1.370(2) . ? C14 C15 1.373(2) . ? C16 O16 1.2316(17) . ? C16 N17 1.3289(18) . ? N17 C18 1.4464(19) . ? C18 C19 1.513(2) . ? C19 N20 1.3330(19) . ? C19 C24 1.381(2) . ? N20 C21 1.342(2) . ? C21 C22 1.366(2) . ? C22 C23 1.369(2) . ? C23 C24 1.373(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 C2 N1 C6 117.21(14) . . ? N1 C2 C3 122.09(15) . . ? N1 C2 C7 114.05(13) . . ? C3 C2 C7 123.85(13) . . ? C2 C3 C4 119.14(16) . . ? C5 C4 C3 119.02(17) . . ? C6 C5 C4 118.38(17) . . ? N1 C6 C5 124.01(16) . . ? N8 C7 C2 115.11(12) . . ? C9 N8 C7 121.81(12) . . ? O9 C9 N8 124.10(14) . . ? O9 C9 C10 120.69(14) . . ? N8 C9 C10 115.16(12) . . ? N11 C10 C15 122.52(14) . . ? N11 C10 C9 117.74(12) . . ? C15 C10 C9 119.66(13) . . ? C10 N11 C12 117.72(11) . . ? N11 C12 C13 122.86(14) . . ? N11 C12 C16 117.16(12) . . ? C13 C12 C16 119.96(13) . . ? C14 C13 C12 118.66(15) . . ? C13 C14 C15 119.30(15) . . ? C14 C15 C10 118.91(15) . . ? O16 C16 N17 123.72(14) . . ? O16 C16 C12 120.85(13) . . ? N17 C16 C12 115.43(12) . . ? C16 N17 C18 122.24(13) . . ? N17 C18 C19 114.74(13) . . ? N20 C19 C24 121.90(15) . . ? N20 C19 C18 118.81(13) . . ? C24 C19 C18 119.28(14) . . ? C19 N20 C21 117.00(13) . . ? N20 C21 C22 124.40(16) . . ? C21 C22 C23 118.05(17) . . ? C22 C23 C24 118.81(16) . . ? C23 C24 C19 119.83(15) . . ? 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 C6 N1 C2 C3 1.7(2) . . . . ? C6 N1 C2 C7 -177.24(14) . . . . ? N1 C2 C3 C4 -3.7(2) . . . . ? C7 C2 C3 C4 175.07(15) . . . . ? C2 C3 C4 C5 2.0(3) . . . . ? C3 C4 C5 C6 1.5(3) . . . . ? C2 N1 C6 C5 2.2(2) . . . . ? C4 C5 C6 N1 -3.8(3) . . . . ? N1 C2 C7 N8 173.98(12) . . . . ? C3 C2 C7 N8 -4.9(2) . . . . ? C2 C7 N8 C9 104.66(16) . . . . ? C7 N8 C9 O9 -8.5(2) . . . . ? C7 N8 C9 C10 168.88(13) . . . . ? O9 C9 C10 N11 -164.92(14) . . . . ? N8 C9 C10 N11 17.61(19) . . . . ? O9 C9 C10 C15 18.1(2) . . . . ? N8 C9 C10 C15 -159.32(14) . . . . ? C15 C10 N11 C12 -1.3(2) . . . . ? C9 C10 N11 C12 -178.18(12) . . . . ? C10 N11 C12 C13 1.9(2) . . . . ? C10 N11 C12 C16 -179.71(12) . . . . ? N11 C12 C13 C14 -1.1(2) . . . . ? C16 C12 C13 C14 -179.48(14) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C10 0.7(3) . . . . ? N11 C10 C15 C14 0.1(2) . . . . ? C9 C10 C15 C14 176.85(15) . . . . ? N11 C12 C16 O16 171.65(13) . . . . ? C13 C12 C16 O16 -9.9(2) . . . . ? N11 C12 C16 N17 -8.90(19) . . . . ? C13 C12 C16 N17 169.56(13) . . . . ? O16 C16 N17 C18 3.9(2) . . . . ? C12 C16 N17 C18 -175.57(13) . . . . ? C16 N17 C18 C19 87.83(18) . . . . ? N17 C18 C19 N20 -5.1(2) . . . . ? N17 C18 C19 C24 175.81(14) . . . . ? C24 C19 N20 C21 -1.0(2) . . . . ? C18 C19 N20 C21 179.88(13) . . . . ? C19 N20 C21 C22 0.5(2) . . . . ? N20 C21 C22 C23 0.1(3) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C19 -0.3(2) . . . . ? N20 C19 C24 C23 1.0(2) . . . . ? C18 C19 C24 C23 -179.94(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8N N11 0.9795(11) 2.294(15) 2.7182(16) 105.1(10) . N17 H17N N11 0.9796(11) 2.271(16) 2.6897(16) 104.6(11) . N8 H8N N20 0.9795(11) 2.450(8) 3.3342(17) 150.0(12) 2 N17 H17N N20 0.9796(11) 2.210(9) 3.0742(18) 146.4(13) 2 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.109 _refine_diff_density_min -0.101 _refine_diff_density_rms 0.025