# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Heirtzler, Fenton' _publ_contact_author_email frheirtzler@alaska.edu _publ_section_title ; A Self-assembled, Metalloorganic Supramolecular Frequency Doubler ; loop_ _publ_author_name F.Heirtzler G.Gonella L.Burke H.-L.Dai S.Jones J.Zubieta ; A.Roche ; # Attachment '- p-1[2] R.cif' data_p-1[2] _database_code_depnum_ccdc_archive 'CCDC 837802' #TrackingRef '- p-1[2] R.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H26 Cu2 N14 O8, 2(F6 P), 3(C2 H3 N)' _chemical_formula_sum 'C56 H41 Cu2 F12 N19 O8 P2' _chemical_formula_weight 1525.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4377(16) _cell_length_b 15.912(3) _cell_length_c 20.940(3) _cell_angle_alpha 72.940(4) _cell_angle_beta 82.840(4) _cell_angle_gamma 78.612(4) _cell_volume 2939.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 14004 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 28.08 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8419 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 29016 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.1214 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 28.08 _reflns_number_total 14004 _reflns_number_gt 7628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CrystalMaker (Palmer, 2006)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2002)' _refine_special_details ; ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.500 136 49 ' ' _platon_squeeze_details ;The unit cell contains 2 acetonitirle molecules which have been treated as a diffuse contribution to the overall scattering without specific arom positions by SQUEEZE/PLATON in addition to the 3 acetonitrile molecules found in the electron density map. 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^)+(0.0815P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14004 _refine_ls_number_parameters 841 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1300 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1773 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 0.48810(6) 0.16422(4) 0.44915(3) 0.02703(16) Uani 1 1 d . . . N3 N 0.3600(4) 0.0885(2) 0.43110(18) 0.0238(8) Uani 1 1 d . . . N2 N 0.6799(4) 0.1641(2) 0.39322(19) 0.0243(8) Uani 1 1 d . . . N4 N 0.4190(4) 0.1037(2) 0.54451(19) 0.0235(8) Uani 1 1 d . . . N5 N 0.3107(4) 0.0098(3) 0.67014(19) 0.0261(9) Uani 1 1 d . . . N1 N 0.4967(4) 0.2950(2) 0.4284(2) 0.0316(10) Uani 1 1 d . . . C17 C 0.2967(5) -0.0118(3) 0.6156(2) 0.0233(10) Uani 1 1 d . . . C19 C 0.4402(5) 0.1240(3) 0.6018(2) 0.0241(10) Uani 1 1 d . . . C11 C 0.3320(5) 0.0857(3) 0.3708(2) 0.0281(11) Uani 1 1 d . . . H11 H 0.3768 0.1220 0.3323 0.034 Uiso 1 1 calc R . . C18 C 0.3766(5) 0.0802(3) 0.6635(2) 0.0241(10) Uani 1 1 d . . . C6 C 0.7185(5) 0.2455(3) 0.3709(2) 0.0267(10) Uani 1 1 d . . . C14 C 0.2018(5) -0.0168(3) 0.4803(2) 0.0269(11) Uani 1 1 d . . . H14 H 0.1560 -0.0517 0.5193 0.032 Uiso 1 1 calc R . . C22 C 0.4604(5) 0.1730(3) 0.7165(3) 0.0305(11) Uani 1 1 d . . . C12 C 0.2423(5) 0.0331(3) 0.3619(3) 0.0330(12) Uani 1 1 d . . . H12 H 0.2286 0.0314 0.3181 0.040 Uiso 1 1 calc R . . O1 O 0.6139(4) 0.3462(3) 0.6048(2) 0.0545(11) Uani 1 1 d . . . C13 C 0.1718(5) -0.0175(3) 0.4170(2) 0.0302(11) Uani 1 1 d . . . H13 H 0.1046 -0.0519 0.4119 0.036 Uiso 1 1 calc R . . N6 N 0.6240(5) 0.2784(3) 0.6516(3) 0.0399(11) Uani 1 1 d . . . C20 C 0.5226(5) 0.1904(3) 0.5986(3) 0.0289(11) Uani 1 1 d . . . H20 H 0.5712 0.2181 0.5575 0.035 Uiso 1 1 calc R . . C5 C 0.6218(5) 0.3176(3) 0.3948(2) 0.0304(11) Uani 1 1 d . . . O3 O 0.4457(5) 0.2883(3) 0.7643(2) 0.0634(13) Uani 1 1 d . . . O4 O 0.4418(5) 0.1560(3) 0.8304(2) 0.0583(12) Uani 1 1 d . . . C15 C 0.2989(5) 0.0351(3) 0.4859(2) 0.0225(10) Uani 1 1 d . . . C16 C 0.3404(5) 0.0416(3) 0.5502(2) 0.0242(10) Uani 1 1 d . . . C21 C 0.5313(5) 0.2140(3) 0.6552(3) 0.0311(12) Uani 1 1 d . . . C9 C 0.8774(5) 0.1110(3) 0.3226(2) 0.0296(11) Uani 1 1 d . . . H9 H 0.9304 0.0634 0.3061 0.036 Uiso 1 1 calc R . . C10 C 0.7581(5) 0.0981(3) 0.3685(2) 0.0238(10) Uani 1 1 d . . . C4 C 0.6569(6) 0.4006(3) 0.3845(3) 0.0386(13) Uani 1 1 d . . . H4 H 0.7466 0.4140 0.3615 0.046 Uiso 1 1 calc R . . C8 C 0.9168(5) 0.1945(3) 0.3014(3) 0.0332(12) Uani 1 1 d . . . H8 H 0.9993 0.2048 0.2710 0.040 Uiso 1 1 calc R . . C7 C 0.8362(5) 0.2619(3) 0.3246(3) 0.0343(12) Uani 1 1 d . . . H7 H 0.8603 0.3201 0.3092 0.041 Uiso 1 1 calc R . . N7 N 0.4528(5) 0.2078(4) 0.7751(3) 0.0440(12) Uani 1 1 d . . . C3 C 0.5603(6) 0.4649(3) 0.4078(3) 0.0461(15) Uani 1 1 d . . . H3A H 0.5821 0.5228 0.4008 0.055 Uiso 1 1 calc R . . C23 C 0.3866(5) 0.1059(3) 0.7212(2) 0.0306(11) Uani 1 1 d . . . H23 H 0.3424 0.0768 0.7630 0.037 Uiso 1 1 calc R . . O2 O 0.7090(5) 0.2596(3) 0.6953(2) 0.0611(12) Uani 1 1 d . . . C2 C 0.4322(6) 0.4423(4) 0.4414(3) 0.0493(16) Uani 1 1 d . . . H2 H 0.3639 0.4848 0.4579 0.059 Uiso 1 1 calc R . . C1 C 0.4038(6) 0.3578(3) 0.4511(3) 0.0405(13) Uani 1 1 d . . . H1 H 0.3153 0.3430 0.4746 0.049 Uiso 1 1 calc R . . Cu2 Cu 0.87137(6) 0.86722(4) 0.04261(3) 0.02471(15) Uani 1 1 d . . . P2 P 0.72307(14) 0.87087(10) 0.83265(7) 0.0328(3) Uani 1 1 d . . . F12 F 0.7594(3) 0.8151(2) 0.77817(14) 0.0397(7) Uani 1 1 d . . . N11 N 0.9916(4) 0.9071(2) -0.04513(18) 0.0206(8) Uani 1 1 d . . . F11 F 0.6164(3) 0.8035(2) 0.87416(14) 0.0416(8) Uani 1 1 d . . . F8 F 0.8325(3) 0.9367(2) 0.79166(15) 0.0468(8) Uani 1 1 d . . . N8 N 0.8138(4) 0.7459(2) 0.06826(19) 0.0238(8) Uani 1 1 d . . . N10 N 0.7619(4) 0.9920(2) 0.00702(18) 0.0212(8) Uani 1 1 d . . . N9 N 0.9270(4) 0.8252(2) 0.13852(18) 0.0230(8) Uani 1 1 d . . . F9 F 0.6883(4) 0.9254(2) 0.88708(16) 0.0531(9) Uani 1 1 d . . . F7 F 0.5930(3) 0.9329(2) 0.79098(16) 0.0492(8) Uani 1 1 d . . . C38 C 0.8188(5) 1.0401(3) -0.0519(2) 0.0221(10) Uani 1 1 d . . . N12 N 1.1375(4) 0.9795(2) -0.16774(18) 0.0244(9) Uani 1 1 d . . . C43 C 1.1472(5) 0.7654(3) -0.0371(2) 0.0270(10) Uani 1 1 d . . . H43 H 1.1054 0.7411 0.0065 0.032 Uiso 1 1 calc R . . F10 F 0.8533(3) 0.8078(2) 0.87407(16) 0.0531(9) Uani 1 1 d . . . C40 C 1.0363(5) 1.0292(3) -0.1398(2) 0.0207(9) Uani 1 1 d . . . C29 C 0.9058(5) 0.7417(3) 0.1707(2) 0.0259(10) Uani 1 1 d . . . C37 C 0.7510(5) 1.1252(3) -0.0836(2) 0.0255(10) Uani 1 1 d . . . H37 H 0.7905 1.1572 -0.1256 0.031 Uiso 1 1 calc R . . C25 C 0.7210(6) 0.6241(3) 0.0526(3) 0.0354(12) Uani 1 1 d . . . H25 H 0.6756 0.6014 0.0248 0.043 Uiso 1 1 calc R . . C28 C 0.8466(5) 0.6960(3) 0.1306(2) 0.0260(10) Uani 1 1 d . . . C39 C 0.9526(4) 0.9919(3) -0.0792(2) 0.0206(9) Uani 1 1 d . . . O5 O 1.4612(4) 0.7253(3) -0.2247(2) 0.0523(11) Uani 1 1 d . . . C41 C 1.1677(5) 0.8911(3) -0.1355(2) 0.0246(10) Uani 1 1 d . . . C33 C 0.9686(5) 0.8738(3) 0.1739(2) 0.0219(10) Uani 1 1 d . . . N14 N 1.4102(5) 0.6903(3) -0.1689(3) 0.0439(12) Uani 1 1 d . . . N13 N 1.3025(6) 0.6219(3) -0.0267(2) 0.0424(12) Uani 1 1 d . . . C42 C 1.1028(5) 0.8549(3) -0.0717(2) 0.0216(10) Uani 1 1 d . . . C36 C 0.6261(5) 1.1629(3) -0.0539(2) 0.0274(11) Uani 1 1 d . . . H36 H 0.5793 1.2215 -0.0750 0.033 Uiso 1 1 calc R . . C44 C 1.2517(5) 0.7135(3) -0.0670(3) 0.0305(11) Uani 1 1 d . . . C45 C 1.3109(5) 0.7480(3) -0.1334(3) 0.0315(12) Uani 1 1 d . . . C46 C 1.2731(5) 0.8359(3) -0.1663(2) 0.0284(11) Uani 1 1 d . . . H46 H 1.3170 0.8599 -0.2095 0.034 Uiso 1 1 calc R . . C24 C 0.7537(5) 0.7096(3) 0.0307(3) 0.0315(11) Uani 1 1 d . . . H24 H 0.7322 0.7442 -0.0135 0.038 Uiso 1 1 calc R . . O8 O 1.2206(5) 0.5696(3) -0.0138(2) 0.0586(12) Uani 1 1 d . . . C30 C 0.9311(5) 0.7035(3) 0.2379(2) 0.0307(11) Uani 1 1 d . . . H30 H 0.9169 0.6440 0.2593 0.037 Uiso 1 1 calc R . . C34 C 0.6409(5) 1.0306(3) 0.0347(2) 0.0285(11) Uani 1 1 d . . . H34 H 0.6018 0.9974 0.0763 0.034 Uiso 1 1 calc R . . C32 C 0.9943(5) 0.8406(3) 0.2414(2) 0.0294(11) Uani 1 1 d . . . H32 H 1.0225 0.8766 0.2650 0.035 Uiso 1 1 calc R . . C31 C 0.9772(5) 0.7526(3) 0.2733(2) 0.0324(12) Uani 1 1 d . . . H31 H 0.9971 0.7268 0.3189 0.039 Uiso 1 1 calc R . . O6 O 1.4361(5) 0.6110(3) -0.1413(3) 0.0774(16) Uani 1 1 d . . . C35 C 0.5697(5) 1.1148(3) 0.0068(2) 0.0305(11) Uani 1 1 d . . . H35 H 0.4840 1.1395 0.0285 0.037 Uiso 1 1 calc R . . C27 C 0.8228(6) 0.6088(3) 0.1548(3) 0.0359(12) Uani 1 1 d . . . H27 H 0.8520 0.5739 0.1978 0.043 Uiso 1 1 calc R . . C26 C 0.7563(6) 0.5728(3) 0.1162(3) 0.0400(13) Uani 1 1 d . . . H26 H 0.7353 0.5139 0.1330 0.048 Uiso 1 1 calc R . . O7 O 1.4229(5) 0.6080(3) -0.0060(3) 0.0738(14) Uani 1 1 d . . . P1 P 0.01064(16) 0.76017(10) 0.48094(8) 0.0416(4) Uani 1 1 d . . . F5 F 0.0475(5) 0.6813(2) 0.54580(18) 0.0701(11) Uani 1 1 d . . . F1 F 0.0368(5) 0.6912(3) 0.4388(2) 0.0872(14) Uani 1 1 d . . . F3 F 0.1746(4) 0.7721(3) 0.4695(2) 0.0720(12) Uani 1 1 d . . . F2 F -0.0313(5) 0.8414(3) 0.4177(2) 0.0979(17) Uani 1 1 d . . . F4 F -0.0122(5) 0.8305(3) 0.5239(2) 0.0871(14) Uani 1 1 d . . . F6 F -0.1534(4) 0.7507(3) 0.4964(3) 0.114(2) Uani 1 1 d . . . N90 N 0.0269(8) 0.4687(4) 0.2954(4) 0.087(2) Uani 1 1 d . . . C91 C 0.1069(7) 0.4022(5) 0.3072(3) 0.0560(17) Uani 1 1 d . . . C90 C 0.2036(7) 0.3178(4) 0.3228(3) 0.0608(18) Uani 1 1 d . . . H90A H 0.1692 0.2794 0.3654 0.091 Uiso 1 1 calc R . . H90B H 0.3011 0.3277 0.3266 0.091 Uiso 1 1 calc R . . H90C H 0.2062 0.2891 0.2871 0.091 Uiso 1 1 calc R . . N91 N -0.0882(9) 0.3620(4) 0.1713(3) 0.086(2) Uani 1 1 d . . . C92 C 0.0221(11) 0.3824(5) 0.1497(4) 0.075(2) Uani 1 1 d . . . C95 C 0.1593(11) 0.4064(5) 0.1229(4) 0.105(3) Uani 1 1 d . . . H95A H 0.1991 0.4286 0.1547 0.158 Uiso 1 1 calc R . . H95B H 0.1476 0.4532 0.0805 0.158 Uiso 1 1 calc R . . H95C H 0.2255 0.3540 0.1152 0.158 Uiso 1 1 calc R . . C98 C 0.3772(9) 0.5541(5) 0.2263(4) 0.081(2) Uani 1 1 d . . . H98A H 0.3153 0.5482 0.2680 0.122 Uiso 1 1 calc R . . H98B H 0.4562 0.5851 0.2278 0.122 Uiso 1 1 calc R . . H98C H 0.4178 0.4947 0.2209 0.122 Uiso 1 1 calc R . . N93 N 0.2247(7) 0.6439(4) 0.1268(4) 0.0777(19) Uani 1 1 d . . . C100 C 0.2919(8) 0.6049(4) 0.1700(4) 0.0554(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0304(3) 0.0235(3) 0.0251(3) -0.0041(3) 0.0044(3) -0.0075(2) N3 0.025(2) 0.024(2) 0.016(2) 0.0001(16) -0.0015(16) 0.0001(16) N2 0.025(2) 0.027(2) 0.020(2) -0.0038(17) -0.0007(16) -0.0068(16) N4 0.026(2) 0.0203(19) 0.023(2) -0.0062(16) 0.0024(16) -0.0024(16) N5 0.026(2) 0.028(2) 0.022(2) -0.0081(17) 0.0021(17) -0.0024(17) N1 0.035(2) 0.020(2) 0.033(2) -0.0028(18) 0.0057(19) -0.0018(18) C17 0.018(2) 0.026(2) 0.024(3) -0.007(2) 0.0048(19) -0.0032(18) C19 0.025(2) 0.022(2) 0.023(3) -0.007(2) -0.0005(19) 0.0020(19) C11 0.035(3) 0.022(2) 0.021(3) 0.001(2) 0.003(2) -0.002(2) C18 0.026(2) 0.025(2) 0.020(2) -0.006(2) 0.0004(19) -0.0020(19) C6 0.029(3) 0.027(2) 0.023(3) -0.003(2) -0.004(2) -0.008(2) C14 0.030(3) 0.028(2) 0.017(2) 0.001(2) 0.001(2) -0.003(2) C22 0.032(3) 0.034(3) 0.030(3) -0.017(2) -0.007(2) 0.001(2) C12 0.041(3) 0.033(3) 0.022(3) -0.003(2) -0.004(2) -0.004(2) O1 0.050(3) 0.032(2) 0.085(3) -0.020(2) 0.000(2) -0.0123(19) C13 0.035(3) 0.030(3) 0.025(3) -0.002(2) -0.007(2) -0.011(2) N6 0.034(3) 0.038(3) 0.052(3) -0.024(3) 0.005(2) -0.006(2) C20 0.026(2) 0.026(2) 0.032(3) -0.006(2) 0.001(2) -0.002(2) C5 0.035(3) 0.028(3) 0.027(3) -0.004(2) -0.005(2) -0.004(2) O3 0.073(3) 0.059(3) 0.074(3) -0.042(3) 0.024(3) -0.028(2) O4 0.071(3) 0.075(3) 0.039(3) -0.027(2) -0.004(2) -0.017(2) C15 0.023(2) 0.019(2) 0.023(3) -0.0037(19) 0.0002(19) -0.0042(18) C16 0.022(2) 0.023(2) 0.026(3) -0.008(2) 0.0011(19) 0.0000(19) C21 0.026(2) 0.028(3) 0.044(3) -0.017(2) 0.000(2) -0.006(2) C9 0.031(3) 0.031(3) 0.023(3) -0.004(2) 0.004(2) -0.002(2) C10 0.024(2) 0.028(2) 0.016(2) -0.0025(19) -0.0026(19) -0.0033(19) C4 0.039(3) 0.029(3) 0.044(3) -0.005(2) 0.004(3) -0.010(2) C8 0.030(3) 0.038(3) 0.030(3) -0.005(2) 0.005(2) -0.012(2) C7 0.036(3) 0.032(3) 0.031(3) -0.001(2) 0.008(2) -0.015(2) N7 0.044(3) 0.053(3) 0.044(3) -0.027(3) 0.004(2) -0.013(2) C3 0.053(4) 0.024(3) 0.062(4) -0.013(3) 0.006(3) -0.012(3) C23 0.031(3) 0.036(3) 0.022(3) -0.008(2) 0.000(2) -0.002(2) O2 0.050(3) 0.082(3) 0.065(3) -0.028(3) -0.009(2) -0.028(2) C2 0.054(4) 0.032(3) 0.060(4) -0.016(3) 0.013(3) -0.006(3) C1 0.044(3) 0.027(3) 0.048(4) -0.009(3) 0.006(3) -0.008(2) Cu2 0.0328(3) 0.0226(3) 0.0166(3) -0.0018(2) -0.0002(2) -0.0062(2) P2 0.0324(7) 0.0481(8) 0.0209(7) -0.0118(6) 0.0023(6) -0.0132(6) F12 0.0406(17) 0.0541(19) 0.0280(17) -0.0189(15) 0.0056(13) -0.0102(14) N11 0.025(2) 0.0219(19) 0.0157(19) -0.0053(16) -0.0016(15) -0.0060(16) F11 0.0443(18) 0.058(2) 0.0289(17) -0.0155(15) 0.0056(14) -0.0244(15) F8 0.054(2) 0.064(2) 0.0284(17) -0.0105(16) 0.0061(15) -0.0337(17) N8 0.030(2) 0.023(2) 0.019(2) -0.0042(16) -0.0019(16) -0.0076(16) N10 0.0240(19) 0.0233(19) 0.017(2) -0.0055(16) 0.0015(16) -0.0068(16) N9 0.027(2) 0.0221(19) 0.018(2) -0.0035(16) 0.0005(16) -0.0055(16) F9 0.062(2) 0.074(2) 0.042(2) -0.0373(18) 0.0161(16) -0.0352(19) F7 0.0447(19) 0.051(2) 0.050(2) -0.0114(17) -0.0130(16) -0.0020(15) C38 0.024(2) 0.026(2) 0.018(2) -0.0074(19) -0.0012(19) -0.0077(19) N12 0.030(2) 0.023(2) 0.020(2) -0.0085(17) 0.0032(17) -0.0051(17) C43 0.028(2) 0.028(2) 0.026(3) -0.007(2) -0.004(2) -0.007(2) F10 0.047(2) 0.073(2) 0.0359(19) -0.0026(17) -0.0124(15) -0.0143(17) C40 0.025(2) 0.025(2) 0.016(2) -0.0048(19) -0.0066(18) -0.0094(19) C29 0.027(2) 0.027(2) 0.021(3) -0.004(2) 0.001(2) -0.006(2) C37 0.032(3) 0.023(2) 0.021(2) -0.003(2) -0.002(2) -0.008(2) C25 0.039(3) 0.032(3) 0.041(3) -0.013(2) -0.005(2) -0.013(2) C28 0.029(3) 0.024(2) 0.023(3) -0.003(2) -0.001(2) -0.006(2) C39 0.018(2) 0.027(2) 0.021(2) -0.0093(19) -0.0035(18) -0.0068(18) O5 0.054(3) 0.057(3) 0.048(3) -0.029(2) 0.014(2) -0.002(2) C41 0.023(2) 0.026(2) 0.024(3) -0.005(2) -0.003(2) -0.0073(19) C33 0.023(2) 0.024(2) 0.020(2) -0.0073(19) -0.0006(19) -0.0053(18) N14 0.038(3) 0.040(3) 0.058(3) -0.027(3) 0.010(2) -0.004(2) N13 0.053(3) 0.031(3) 0.041(3) -0.014(2) -0.006(2) 0.007(2) C42 0.027(2) 0.022(2) 0.019(2) -0.0085(19) -0.0041(19) -0.0072(19) C36 0.029(3) 0.024(2) 0.027(3) -0.007(2) -0.001(2) 0.001(2) C44 0.033(3) 0.020(2) 0.038(3) -0.008(2) -0.004(2) -0.004(2) C45 0.027(3) 0.034(3) 0.039(3) -0.019(2) 0.004(2) -0.006(2) C46 0.027(2) 0.037(3) 0.025(3) -0.014(2) 0.007(2) -0.011(2) C24 0.039(3) 0.030(3) 0.025(3) -0.009(2) 0.001(2) -0.005(2) O8 0.078(3) 0.030(2) 0.065(3) -0.004(2) -0.003(2) -0.016(2) C30 0.042(3) 0.023(2) 0.024(3) 0.004(2) -0.002(2) -0.013(2) C34 0.035(3) 0.033(3) 0.018(2) -0.009(2) 0.003(2) -0.009(2) C32 0.033(3) 0.035(3) 0.021(3) -0.005(2) -0.002(2) -0.010(2) C31 0.041(3) 0.036(3) 0.019(3) 0.000(2) -0.005(2) -0.012(2) O6 0.092(4) 0.037(3) 0.090(4) -0.025(3) 0.034(3) 0.006(2) C35 0.025(2) 0.037(3) 0.028(3) -0.010(2) 0.000(2) -0.001(2) C27 0.046(3) 0.027(3) 0.032(3) 0.000(2) -0.006(2) -0.011(2) C26 0.060(4) 0.025(3) 0.034(3) -0.002(2) -0.005(3) -0.013(3) O7 0.061(3) 0.056(3) 0.092(4) -0.008(3) -0.030(3) 0.014(2) P1 0.0350(8) 0.0338(8) 0.0496(10) 0.0000(7) -0.0039(7) -0.0079(6) F5 0.106(3) 0.053(2) 0.044(2) 0.0022(18) -0.005(2) -0.019(2) F1 0.138(4) 0.083(3) 0.051(3) -0.025(2) -0.016(3) -0.028(3) F3 0.038(2) 0.069(3) 0.098(3) -0.013(2) 0.002(2) -0.0045(18) F2 0.120(4) 0.062(3) 0.101(4) 0.038(2) -0.066(3) -0.046(3) F4 0.086(3) 0.055(2) 0.126(4) -0.046(3) 0.015(3) -0.007(2) F6 0.041(2) 0.067(3) 0.209(6) 0.006(3) -0.010(3) -0.021(2) N90 0.092(5) 0.047(4) 0.102(6) 0.012(4) -0.020(4) -0.003(3) C91 0.059(4) 0.051(4) 0.057(4) -0.005(3) -0.010(3) -0.019(3) C90 0.062(4) 0.062(4) 0.060(4) -0.023(4) -0.008(3) -0.002(3) N91 0.130(7) 0.049(4) 0.066(5) 0.002(3) -0.019(4) -0.007(4) C92 0.123(8) 0.048(4) 0.045(4) 0.000(3) 0.008(5) -0.024(5) C95 0.165(9) 0.060(5) 0.090(7) -0.024(5) 0.055(6) -0.054(6) C98 0.089(6) 0.066(5) 0.090(6) -0.017(5) -0.005(5) -0.024(4) N93 0.087(5) 0.059(4) 0.076(5) -0.010(4) 0.007(4) -0.007(3) C100 0.071(5) 0.041(4) 0.053(4) -0.011(3) 0.009(4) -0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.003(4) . ? Cu1 N1 2.013(4) . ? Cu1 N2 2.030(4) . ? Cu1 N4 2.034(4) . ? N3 C11 1.337(6) . ? N3 C15 1.352(5) . ? N2 C6 1.348(6) . ? N2 C10 1.354(6) . ? N4 C16 1.319(6) . ? N4 C19 1.377(6) . ? N5 C17 1.313(6) . ? N5 C18 1.351(6) . ? N1 C1 1.350(6) . ? N1 C5 1.353(6) . ? C17 C16 1.443(6) . ? C17 C10 1.494(6) 2_656 ? C19 C18 1.399(6) . ? C19 C20 1.413(6) . ? C11 C12 1.364(7) . ? C11 H11 0.9500 . ? C18 C23 1.403(6) . ? C6 C7 1.392(6) . ? C6 C5 1.486(6) . ? C14 C15 1.385(6) . ? C14 C13 1.392(6) . ? C14 H14 0.9500 . ? C22 C23 1.360(7) . ? C22 C21 1.411(7) . ? C22 N7 1.475(6) . ? C12 C13 1.377(7) . ? C12 H12 0.9500 . ? O1 N6 1.222(6) . ? C13 H13 0.9500 . ? N6 O2 1.225(6) . ? N6 C21 1.454(6) . ? C20 C21 1.362(7) . ? C20 H20 0.9500 . ? C5 C4 1.375(7) . ? O3 N7 1.222(6) . ? O4 N7 1.214(6) . ? C15 C16 1.487(6) . ? C9 C8 1.382(7) . ? C9 C10 1.393(6) . ? C9 H9 0.9500 . ? C10 C17 1.494(6) 2_656 ? C4 C3 1.388(7) . ? C4 H4 0.9500 . ? C8 C7 1.363(7) . ? C8 H8 0.9500 . ? C7 H7 0.9500 . ? C3 C2 1.377(8) . ? C3 H3A 0.9500 . ? C23 H23 0.9500 . ? C2 C1 1.375(7) . ? C2 H2 0.9500 . ? C1 H1 0.9500 . ? Cu2 N8 2.010(4) . ? Cu2 N10 2.020(4) . ? Cu2 N9 2.023(4) . ? Cu2 N11 2.036(4) . ? P2 F7 1.589(3) . ? P2 F9 1.591(3) . ? P2 F10 1.593(3) . ? P2 F11 1.606(3) . ? P2 F8 1.606(3) . ? P2 F12 1.607(3) . ? N11 C39 1.331(5) . ? N11 C42 1.372(5) . ? N8 C24 1.336(6) . ? N8 C28 1.351(6) . ? N10 C34 1.335(6) . ? N10 C38 1.356(5) . ? N9 C29 1.344(6) . ? N9 C33 1.353(5) . ? C38 C37 1.385(6) . ? C38 C39 1.486(6) . ? N12 C40 1.309(5) . ? N12 C41 1.360(6) . ? C43 C44 1.369(6) . ? C43 C42 1.401(6) . ? C43 H43 0.9500 . ? C40 C39 1.442(6) . ? C40 C33 1.493(6) 2_775 ? C29 C30 1.390(6) . ? C29 C28 1.476(6) . ? C37 C36 1.376(6) . ? C37 H37 0.9500 . ? C25 C26 1.384(7) . ? C25 C24 1.385(7) . ? C25 H25 0.9500 . ? C28 C27 1.383(6) . ? O5 N14 1.221(6) . ? C41 C42 1.405(6) . ? C41 C46 1.416(6) . ? C33 C32 1.389(6) . ? C33 C40 1.493(6) 2_775 ? N14 O6 1.213(6) . ? N14 C45 1.470(6) . ? N13 O8 1.197(6) . ? N13 O7 1.223(6) . ? N13 C44 1.472(6) . ? C36 C35 1.381(6) . ? C36 H36 0.9500 . ? C44 C45 1.424(7) . ? C45 C46 1.362(7) . ? C46 H46 0.9500 . ? C24 H24 0.9500 . ? C30 C31 1.380(7) . ? C30 H30 0.9500 . ? C34 C35 1.368(7) . ? C34 H34 0.9500 . ? C32 C31 1.395(7) . ? C32 H32 0.9500 . ? C31 H31 0.9500 . ? C35 H35 0.9500 . ? C27 C26 1.385(7) . ? C27 H27 0.9500 . ? C26 H26 0.9500 . ? P1 F1 1.566(4) . ? P1 F6 1.569(4) . ? P1 F3 1.576(4) . ? P1 F5 1.577(4) . ? P1 F2 1.583(4) . ? P1 F4 1.599(4) . ? N90 C91 1.153(8) . ? C91 C90 1.440(9) . ? C90 H90A 0.9800 . ? C90 H90B 0.9800 . ? C90 H90C 0.9800 . ? N91 C92 1.150(10) . ? C92 C95 1.423(12) . ? C95 H95A 0.9800 . ? C95 H95B 0.9800 . ? C95 H95C 0.9800 . ? C98 C100 1.453(10) . ? C98 H98A 0.9800 . ? C98 H98B 0.9800 . ? C98 H98C 0.9800 . ? N93 C100 1.124(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 N3 Cu1 N1 137.48(16) . . ? N3 Cu1 N2 114.23(15) . . ? N1 Cu1 N2 81.96(15) . . ? N3 Cu1 N4 79.96(15) . . ? N1 Cu1 N4 116.27(15) . . ? N2 Cu1 N4 136.33(15) . . ? C11 N3 C15 118.2(4) . . ? C11 N3 Cu1 126.2(3) . . ? C15 N3 Cu1 115.6(3) . . ? C6 N2 C10 118.0(4) . . ? C6 N2 Cu1 112.9(3) . . ? C10 N2 Cu1 128.3(3) . . ? C16 N4 C19 118.1(4) . . ? C16 N4 Cu1 115.1(3) . . ? C19 N4 Cu1 126.8(3) . . ? C17 N5 C18 117.8(4) . . ? C1 N1 C5 117.7(4) . . ? C1 N1 Cu1 128.0(3) . . ? C5 N1 Cu1 113.7(3) . . ? N5 C17 C16 121.3(4) . . ? N5 C17 C10 111.7(4) . 2_656 ? C16 C17 C10 126.9(4) . 2_656 ? N4 C19 C18 119.9(4) . . ? N4 C19 C20 120.5(4) . . ? C18 C19 C20 119.7(4) . . ? N3 C11 C12 123.3(4) . . ? N3 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? N5 C18 C19 121.5(4) . . ? N5 C18 C23 118.1(4) . . ? C19 C18 C23 120.3(4) . . ? N2 C6 C7 121.7(4) . . ? N2 C6 C5 116.0(4) . . ? C7 C6 C5 122.2(4) . . ? C15 C14 C13 119.4(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C23 C22 C21 120.7(4) . . ? C23 C22 N7 118.5(5) . . ? C21 C22 N7 120.5(4) . . ? C11 C12 C13 119.3(5) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 118.2(5) . . ? C12 C13 H13 120.9 . . ? C14 C13 H13 120.9 . . ? O1 N6 O2 124.7(5) . . ? O1 N6 C21 118.2(5) . . ? O2 N6 C21 117.1(5) . . ? C21 C20 C19 118.9(5) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? N1 C5 C4 122.3(4) . . ? N1 C5 C6 114.8(4) . . ? C4 C5 C6 122.8(5) . . ? N3 C15 C14 121.3(4) . . ? N3 C15 C16 113.8(4) . . ? C14 C15 C16 124.8(4) . . ? N4 C16 C17 120.1(4) . . ? N4 C16 C15 115.0(4) . . ? C17 C16 C15 124.9(4) . . ? C20 C21 C22 121.1(4) . . ? C20 C21 N6 117.9(5) . . ? C22 C21 N6 120.9(5) . . ? C8 C9 C10 118.6(4) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N2 C10 C9 122.5(4) . . ? N2 C10 C17 118.5(4) . 2_656 ? C9 C10 C17 118.5(4) . 2_656 ? C5 C4 C3 119.6(5) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C7 C8 C9 119.3(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C7 C6 120.0(5) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? O4 N7 O3 124.6(5) . . ? O4 N7 C22 117.8(5) . . ? O3 N7 C22 117.3(5) . . ? C2 C3 C4 118.2(5) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C22 C23 C18 119.2(5) . . ? C22 C23 H23 120.4 . . ? C18 C23 H23 120.4 . . ? C1 C2 C3 119.7(5) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? N1 C1 C2 122.6(5) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? N8 Cu2 N10 133.10(15) . . ? N8 Cu2 N9 81.34(15) . . ? N10 Cu2 N9 119.56(14) . . ? N8 Cu2 N11 119.03(14) . . ? N10 Cu2 N11 80.29(14) . . ? N9 Cu2 N11 131.03(15) . . ? F7 P2 F9 90.91(19) . . ? F7 P2 F10 179.3(2) . . ? F9 P2 F10 89.7(2) . . ? F7 P2 F11 90.31(18) . . ? F9 P2 F11 90.58(17) . . ? F10 P2 F11 89.39(18) . . ? F7 P2 F8 90.78(19) . . ? F9 P2 F8 89.69(17) . . ? F10 P2 F8 89.51(18) . . ? F11 P2 F8 178.9(2) . . ? F7 P2 F12 89.66(17) . . ? F9 P2 F12 179.4(2) . . ? F10 P2 F12 89.74(18) . . ? F11 P2 F12 89.33(16) . . ? F8 P2 F12 90.39(16) . . ? C39 N11 C42 119.0(4) . . ? C39 N11 Cu2 114.6(3) . . ? C42 N11 Cu2 126.4(3) . . ? C24 N8 C28 118.1(4) . . ? C24 N8 Cu2 127.9(3) . . ? C28 N8 Cu2 113.9(3) . . ? C34 N10 C38 117.8(4) . . ? C34 N10 Cu2 127.1(3) . . ? C38 N10 Cu2 115.1(3) . . ? C29 N9 C33 118.3(4) . . ? C29 N9 Cu2 113.9(3) . . ? C33 N9 Cu2 127.4(3) . . ? N10 C38 C37 121.2(4) . . ? N10 C38 C39 114.1(4) . . ? C37 C38 C39 124.6(4) . . ? C40 N12 C41 117.6(4) . . ? C44 C43 C42 119.1(4) . . ? C44 C43 H43 120.5 . . ? C42 C43 H43 120.5 . . ? N12 C40 C39 122.0(4) . . ? N12 C40 C33 111.9(4) . 2_775 ? C39 C40 C33 125.8(4) . 2_775 ? N9 C29 C30 121.8(4) . . ? N9 C29 C28 115.2(4) . . ? C30 C29 C28 122.9(4) . . ? C36 C37 C38 119.6(4) . . ? C36 C37 H37 120.2 . . ? C38 C37 H37 120.2 . . ? C26 C25 C24 118.3(5) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? N8 C28 C27 121.6(4) . . ? N8 C28 C29 115.3(4) . . ? C27 C28 C29 123.1(4) . . ? N11 C39 C40 119.5(4) . . ? N11 C39 C38 115.5(4) . . ? C40 C39 C38 124.9(4) . . ? N12 C41 C42 121.7(4) . . ? N12 C41 C46 118.3(4) . . ? C42 C41 C46 119.9(4) . . ? N9 C33 C32 123.1(4) . . ? N9 C33 C40 116.2(4) . 2_775 ? C32 C33 C40 120.0(4) . 2_775 ? O6 N14 O5 123.9(5) . . ? O6 N14 C45 118.3(5) . . ? O5 N14 C45 117.7(5) . . ? O8 N13 O7 125.8(5) . . ? O8 N13 C44 118.0(5) . . ? O7 N13 C44 116.1(5) . . ? N11 C42 C43 120.5(4) . . ? N11 C42 C41 119.2(4) . . ? C43 C42 C41 120.2(4) . . ? C37 C36 C35 119.3(4) . . ? C37 C36 H36 120.4 . . ? C35 C36 H36 120.4 . . ? C43 C44 C45 121.0(4) . . ? C43 C44 N13 117.0(4) . . ? C45 C44 N13 121.9(4) . . ? C46 C45 C44 120.2(4) . . ? C46 C45 N14 118.3(5) . . ? C44 C45 N14 121.5(5) . . ? C45 C46 C41 119.3(4) . . ? C45 C46 H46 120.3 . . ? C41 C46 H46 120.3 . . ? N8 C24 C25 123.5(5) . . ? N8 C24 H24 118.3 . . ? C25 C24 H24 118.3 . . ? C31 C30 C29 119.6(4) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? N10 C34 C35 124.2(4) . . ? N10 C34 H34 117.9 . . ? C35 C34 H34 117.9 . . ? C33 C32 C31 117.7(5) . . ? C33 C32 H32 121.1 . . ? C31 C32 H32 121.1 . . ? C30 C31 C32 119.4(5) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C34 C35 C36 118.0(4) . . ? C34 C35 H35 121.0 . . ? C36 C35 H35 121.0 . . ? C28 C27 C26 119.8(5) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C25 C26 C27 118.7(5) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? F1 P1 F6 91.4(3) . . ? F1 P1 F3 92.1(3) . . ? F6 P1 F3 176.2(3) . . ? F1 P1 F5 89.6(2) . . ? F6 P1 F5 89.1(3) . . ? F3 P1 F5 89.6(2) . . ? F1 P1 F2 92.4(3) . . ? F6 P1 F2 89.4(3) . . ? F3 P1 F2 91.8(2) . . ? F5 P1 F2 177.6(3) . . ? F1 P1 F4 178.7(3) . . ? F6 P1 F4 89.9(3) . . ? F3 P1 F4 86.6(2) . . ? F5 P1 F4 90.2(2) . . ? F2 P1 F4 87.8(3) . . ? N90 C91 C90 178.5(8) . . ? C91 C90 H90A 109.5 . . ? C91 C90 H90B 109.5 . . ? H90A C90 H90B 109.5 . . ? C91 C90 H90C 109.5 . . ? H90A C90 H90C 109.5 . . ? H90B C90 H90C 109.5 . . ? N91 C92 C95 179.3(9) . . ? C92 C95 H95A 109.5 . . ? C92 C95 H95B 109.5 . . ? H95A C95 H95B 109.5 . . ? C92 C95 H95C 109.5 . . ? H95A C95 H95C 109.5 . . ? H95B C95 H95C 109.5 . . ? C100 C98 H98A 109.5 . . ? C100 C98 H98B 109.5 . . ? H98A C98 H98B 109.5 . . ? C100 C98 H98C 109.5 . . ? H98A C98 H98C 109.5 . . ? H98B C98 H98C 109.5 . . ? N93 C100 C98 179.3(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N3 C11 60.2(4) . . . . ? N2 Cu1 N3 C11 -45.1(4) . . . . ? N4 Cu1 N3 C11 178.4(4) . . . . ? N1 Cu1 N3 C15 -120.7(3) . . . . ? N2 Cu1 N3 C15 134.0(3) . . . . ? N4 Cu1 N3 C15 -2.5(3) . . . . ? N3 Cu1 N2 C6 139.1(3) . . . . ? N1 Cu1 N2 C6 0.3(3) . . . . ? N4 Cu1 N2 C6 -119.7(3) . . . . ? N3 Cu1 N2 C10 -30.2(4) . . . . ? N1 Cu1 N2 C10 -169.0(4) . . . . ? N4 Cu1 N2 C10 71.1(4) . . . . ? N3 Cu1 N4 C16 5.9(3) . . . . ? N1 Cu1 N4 C16 144.2(3) . . . . ? N2 Cu1 N4 C16 -108.8(3) . . . . ? N3 Cu1 N4 C19 -170.8(4) . . . . ? N1 Cu1 N4 C19 -32.4(4) . . . . ? N2 Cu1 N4 C19 74.5(4) . . . . ? N3 Cu1 N1 C1 66.9(5) . . . . ? N2 Cu1 N1 C1 -175.7(5) . . . . ? N4 Cu1 N1 C1 -37.6(5) . . . . ? N3 Cu1 N1 C5 -122.4(3) . . . . ? N2 Cu1 N1 C5 -5.1(3) . . . . ? N4 Cu1 N1 C5 133.0(3) . . . . ? C18 N5 C17 C16 -4.6(6) . . . . ? C18 N5 C17 C10 171.7(4) . . . 2_656 ? C16 N4 C19 C18 -1.2(6) . . . . ? Cu1 N4 C19 C18 175.4(3) . . . . ? C16 N4 C19 C20 -179.5(4) . . . . ? Cu1 N4 C19 C20 -3.0(6) . . . . ? C15 N3 C11 C12 1.6(7) . . . . ? Cu1 N3 C11 C12 -179.3(3) . . . . ? C17 N5 C18 C19 -5.8(6) . . . . ? C17 N5 C18 C23 177.5(4) . . . . ? N4 C19 C18 N5 9.1(6) . . . . ? C20 C19 C18 N5 -172.6(4) . . . . ? N4 C19 C18 C23 -174.3(4) . . . . ? C20 C19 C18 C23 4.1(6) . . . . ? C10 N2 C6 C7 -0.9(7) . . . . ? Cu1 N2 C6 C7 -171.4(4) . . . . ? C10 N2 C6 C5 174.7(4) . . . . ? Cu1 N2 C6 C5 4.2(5) . . . . ? N3 C11 C12 C13 2.5(7) . . . . ? C11 C12 C13 C14 -3.7(7) . . . . ? C15 C14 C13 C12 0.9(7) . . . . ? N4 C19 C20 C21 174.5(4) . . . . ? C18 C19 C20 C21 -3.8(7) . . . . ? C1 N1 C5 C4 1.2(8) . . . . ? Cu1 N1 C5 C4 -170.5(4) . . . . ? C1 N1 C5 C6 -179.6(5) . . . . ? Cu1 N1 C5 C6 8.7(5) . . . . ? N2 C6 C5 N1 -8.7(6) . . . . ? C7 C6 C5 N1 166.9(5) . . . . ? N2 C6 C5 C4 170.5(5) . . . . ? C7 C6 C5 C4 -13.9(8) . . . . ? C11 N3 C15 C14 -4.4(6) . . . . ? Cu1 N3 C15 C14 176.4(3) . . . . ? C11 N3 C15 C16 178.4(4) . . . . ? Cu1 N3 C15 C16 -0.9(5) . . . . ? C13 C14 C15 N3 3.2(7) . . . . ? C13 C14 C15 C16 -179.9(4) . . . . ? C19 N4 C16 C17 -8.9(6) . . . . ? Cu1 N4 C16 C17 174.1(3) . . . . ? C19 N4 C16 C15 169.0(4) . . . . ? Cu1 N4 C16 C15 -8.0(5) . . . . ? N5 C17 C16 N4 12.4(6) . . . . ? C10 C17 C16 N4 -163.3(4) 2_656 . . . ? N5 C17 C16 C15 -165.3(4) . . . . ? C10 C17 C16 C15 19.1(7) 2_656 . . . ? N3 C15 C16 N4 5.9(5) . . . . ? C14 C15 C16 N4 -171.3(4) . . . . ? N3 C15 C16 C17 -176.3(4) . . . . ? C14 C15 C16 C17 6.5(7) . . . . ? C19 C20 C21 C22 0.4(7) . . . . ? C19 C20 C21 N6 176.2(4) . . . . ? C23 C22 C21 C20 2.9(7) . . . . ? N7 C22 C21 C20 -171.1(4) . . . . ? C23 C22 C21 N6 -172.8(4) . . . . ? N7 C22 C21 N6 13.2(7) . . . . ? O1 N6 C21 C20 47.4(6) . . . . ? O2 N6 C21 C20 -131.2(5) . . . . ? O1 N6 C21 C22 -136.7(5) . . . . ? O2 N6 C21 C22 44.6(6) . . . . ? C6 N2 C10 C9 1.4(7) . . . . ? Cu1 N2 C10 C9 170.2(3) . . . . ? C6 N2 C10 C17 -170.6(4) . . . 2_656 ? Cu1 N2 C10 C17 -1.8(6) . . . 2_656 ? C8 C9 C10 N2 -0.2(7) . . . . ? C8 C9 C10 C17 171.9(4) . . . 2_656 ? N1 C5 C4 C3 -1.4(8) . . . . ? C6 C5 C4 C3 179.5(5) . . . . ? C10 C9 C8 C7 -1.7(8) . . . . ? C9 C8 C7 C6 2.2(8) . . . . ? N2 C6 C7 C8 -0.9(8) . . . . ? C5 C6 C7 C8 -176.3(5) . . . . ? C23 C22 N7 O4 32.6(7) . . . . ? C21 C22 N7 O4 -153.3(5) . . . . ? C23 C22 N7 O3 -141.3(5) . . . . ? C21 C22 N7 O3 32.8(7) . . . . ? C5 C4 C3 C2 0.6(9) . . . . ? C21 C22 C23 C18 -2.6(7) . . . . ? N7 C22 C23 C18 171.5(4) . . . . ? N5 C18 C23 C22 175.9(4) . . . . ? C19 C18 C23 C22 -0.8(7) . . . . ? C4 C3 C2 C1 0.2(9) . . . . ? C5 N1 C1 C2 -0.3(8) . . . . ? Cu1 N1 C1 C2 170.0(5) . . . . ? C3 C2 C1 N1 -0.4(10) . . . . ? N8 Cu2 N11 C39 139.3(3) . . . . ? N10 Cu2 N11 C39 5.0(3) . . . . ? N9 Cu2 N11 C39 -116.0(3) . . . . ? N8 Cu2 N11 C42 -39.0(4) . . . . ? N10 Cu2 N11 C42 -173.3(4) . . . . ? N9 Cu2 N11 C42 65.8(4) . . . . ? N10 Cu2 N8 C24 55.8(4) . . . . ? N9 Cu2 N8 C24 178.5(4) . . . . ? N11 Cu2 N8 C24 -49.0(4) . . . . ? N10 Cu2 N8 C28 -126.9(3) . . . . ? N9 Cu2 N8 C28 -4.1(3) . . . . ? N11 Cu2 N8 C28 128.3(3) . . . . ? N8 Cu2 N10 C34 55.8(4) . . . . ? N9 Cu2 N10 C34 -51.3(4) . . . . ? N11 Cu2 N10 C34 176.8(4) . . . . ? N8 Cu2 N10 C38 -123.3(3) . . . . ? N9 Cu2 N10 C38 129.6(3) . . . . ? N11 Cu2 N10 C38 -2.3(3) . . . . ? N8 Cu2 N9 C29 2.1(3) . . . . ? N10 Cu2 N9 C29 137.2(3) . . . . ? N11 Cu2 N9 C29 -119.1(3) . . . . ? N8 Cu2 N9 C33 -171.2(4) . . . . ? N10 Cu2 N9 C33 -36.1(4) . . . . ? N11 Cu2 N9 C33 67.6(4) . . . . ? C34 N10 C38 C37 -2.3(6) . . . . ? Cu2 N10 C38 C37 176.9(3) . . . . ? C34 N10 C38 C39 -179.6(4) . . . . ? Cu2 N10 C38 C39 -0.4(5) . . . . ? C41 N12 C40 C39 -3.8(6) . . . . ? C41 N12 C40 C33 170.4(4) . . . 2_775 ? C33 N9 C29 C30 -2.7(6) . . . . ? Cu2 N9 C29 C30 -176.7(4) . . . . ? C33 N9 C29 C28 174.1(4) . . . . ? Cu2 N9 C29 C28 0.1(5) . . . . ? N10 C38 C37 C36 2.1(7) . . . . ? C39 C38 C37 C36 179.2(4) . . . . ? C24 N8 C28 C27 1.7(7) . . . . ? Cu2 N8 C28 C27 -175.9(4) . . . . ? C24 N8 C28 C29 -177.0(4) . . . . ? Cu2 N8 C28 C29 5.3(5) . . . . ? N9 C29 C28 N8 -3.7(6) . . . . ? C30 C29 C28 N8 173.1(4) . . . . ? N9 C29 C28 C27 177.6(4) . . . . ? C30 C29 C28 C27 -5.6(7) . . . . ? C42 N11 C39 C40 -5.8(6) . . . . ? Cu2 N11 C39 C40 175.7(3) . . . . ? C42 N11 C39 C38 171.7(4) . . . . ? Cu2 N11 C39 C38 -6.7(5) . . . . ? N12 C40 C39 N11 9.8(6) . . . . ? C33 C40 C39 N11 -163.5(4) 2_775 . . . ? N12 C40 C39 C38 -167.6(4) . . . . ? C33 C40 C39 C38 19.1(7) 2_775 . . . ? N10 C38 C39 N11 4.7(6) . . . . ? C37 C38 C39 N11 -172.5(4) . . . . ? N10 C38 C39 C40 -177.8(4) . . . . ? C37 C38 C39 C40 4.9(7) . . . . ? C40 N12 C41 C42 -5.6(7) . . . . ? C40 N12 C41 C46 177.7(4) . . . . ? C29 N9 C33 C32 1.9(6) . . . . ? Cu2 N9 C33 C32 175.0(3) . . . . ? C29 N9 C33 C40 -168.8(4) . . . 2_775 ? Cu2 N9 C33 C40 4.3(5) . . . 2_775 ? C39 N11 C42 C43 179.7(4) . . . . ? Cu2 N11 C42 C43 -2.1(6) . . . . ? C39 N11 C42 C41 -3.1(6) . . . . ? Cu2 N11 C42 C41 175.1(3) . . . . ? C44 C43 C42 N11 175.6(4) . . . . ? C44 C43 C42 C41 -1.6(7) . . . . ? N12 C41 C42 N11 9.3(7) . . . . ? C46 C41 C42 N11 -174.1(4) . . . . ? N12 C41 C42 C43 -173.5(4) . . . . ? C46 C41 C42 C43 3.2(7) . . . . ? C38 C37 C36 C35 -0.7(7) . . . . ? C42 C43 C44 C45 -2.7(7) . . . . ? C42 C43 C44 N13 175.6(4) . . . . ? O8 N13 C44 C43 69.7(6) . . . . ? O7 N13 C44 C43 -106.1(6) . . . . ? O8 N13 C44 C45 -112.1(6) . . . . ? O7 N13 C44 C45 72.2(7) . . . . ? C43 C44 C45 C46 5.6(8) . . . . ? N13 C44 C45 C46 -172.6(5) . . . . ? C43 C44 C45 N14 -172.6(5) . . . . ? N13 C44 C45 N14 9.2(8) . . . . ? O6 N14 C45 C46 -175.1(5) . . . . ? O5 N14 C45 C46 4.7(7) . . . . ? O6 N14 C45 C44 3.2(8) . . . . ? O5 N14 C45 C44 -177.0(5) . . . . ? C44 C45 C46 C41 -4.0(7) . . . . ? N14 C45 C46 C41 174.3(4) . . . . ? N12 C41 C46 C45 176.5(4) . . . . ? C42 C41 C46 C45 -0.3(7) . . . . ? C28 N8 C24 C25 1.1(7) . . . . ? Cu2 N8 C24 C25 178.4(4) . . . . ? C26 C25 C24 N8 -1.9(8) . . . . ? N9 C29 C30 C31 1.0(7) . . . . ? C28 C29 C30 C31 -175.5(4) . . . . ? C38 N10 C34 C35 1.1(7) . . . . ? Cu2 N10 C34 C35 -178.0(4) . . . . ? N9 C33 C32 C31 0.6(7) . . . . ? C40 C33 C32 C31 171.0(4) 2_775 . . . ? C29 C30 C31 C32 1.5(7) . . . . ? C33 C32 C31 C30 -2.2(7) . . . . ? N10 C34 C35 C36 0.3(7) . . . . ? C37 C36 C35 C34 -0.4(7) . . . . ? N8 C28 C27 C26 -3.7(8) . . . . ? C29 C28 C27 C26 174.9(5) . . . . ? C24 C25 C26 C27 -0.2(8) . . . . ? C28 C27 C26 C25 2.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.832 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.148