# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Wen-Yann Yeh' _publ_contact_author_email WENYANN@MAIL.NSYSU.EDU.TW _publ_section_title ; Coordination of NO2- ligand to Cu(I) ion in an O,O-bidentate fashion that evolves NO gas upon protonation: a model reaction relevant to denitrification process ; loop_ _publ_author_name 'Wen-Yann Yeh' 'Chi-Shian Chen' # Attachment 'compound_2.cif' data_7389 _database_code_depnum_ccdc_archive 'CCDC 759228' #TrackingRef 'compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C87 H68 B2 Cl2 Cu2 F8 N6 P4' _chemical_formula_sum 'C87 H68 B2 Cl2 Cu2 F8 N6 P4' _chemical_formula_weight 1692.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.8700(2) _cell_length_b 15.1448(2) _cell_length_c 23.0511(3) _cell_angle_alpha 98.7830(10) _cell_angle_beta 93.5300(10) _cell_angle_gamma 101.6710(10) _cell_volume 4328.59(10) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 47609 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1732 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7359 _exptl_absorpt_correction_T_max 0.9997 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52637 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0851 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.38 _reflns_number_total 15746 _reflns_number_gt 10956 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1167P)^2^+4.2037P] 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 15746 _refine_ls_number_parameters 952 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1201 _refine_ls_R_factor_gt 0.0899 _refine_ls_wR_factor_ref 0.2540 _refine_ls_wR_factor_gt 0.2385 _refine_ls_goodness_of_fit_ref 1.240 _refine_ls_restrained_S_all 1.240 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.013 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9224(5) 0.9127(4) 0.1724(3) 0.0388(14) Uani 1 1 d . . . C2 C 0.9812(5) 0.9045(5) 0.2235(3) 0.0485(16) Uani 1 1 d . . . H2 H 0.9472 0.8976 0.2575 0.058 Uiso 1 1 calc R . . C3 C 1.0899(6) 0.9065(5) 0.2244(4) 0.063(2) Uani 1 1 d . . . H3 H 1.1280 0.9016 0.2590 0.076 Uiso 1 1 calc R . . C4 C 1.1408(6) 0.9156(6) 0.1742(5) 0.074(2) Uani 1 1 d . . . H4 H 1.2135 0.9176 0.1745 0.088 Uiso 1 1 calc R . . C5 C 1.0827(7) 0.9218(7) 0.1236(5) 0.082(3) Uani 1 1 d . . . H5 H 1.1166 0.9264 0.0894 0.098 Uiso 1 1 calc R . . C6 C 0.9752(6) 0.9213(6) 0.1221(3) 0.0568(19) Uani 1 1 d . . . H6 H 0.9380 0.9267 0.0873 0.068 Uiso 1 1 calc R . . C7 C 0.8042(5) 1.0332(4) 0.2278(3) 0.0345(13) Uani 1 1 d . . . C8 C 0.9020(6) 1.0966(5) 0.2413(3) 0.0532(18) Uani 1 1 d . . . H8 H 0.9614 1.0855 0.2228 0.064 Uiso 1 1 calc R . . C9 C 0.9104(7) 1.1756(5) 0.2820(4) 0.067(2) Uani 1 1 d . . . H9 H 0.9746 1.2184 0.2897 0.080 Uiso 1 1 calc R . . C10 C 0.8235(6) 1.1908(5) 0.3113(3) 0.0577(19) Uani 1 1 d . . . H10 H 0.8305 1.2421 0.3403 0.069 Uiso 1 1 calc R . . C11 C 0.7273(6) 1.1307(4) 0.2977(3) 0.0470(16) Uani 1 1 d . . . H11 H 0.6681 1.1428 0.3160 0.056 Uiso 1 1 calc R . . C12 C 0.7182(6) 1.0518(4) 0.2568(3) 0.0422(15) Uani 1 1 d . . . H12 H 0.6529 1.0104 0.2486 0.051 Uiso 1 1 calc R . . C13 C 0.7500(5) 0.9521(4) 0.1058(3) 0.0361(14) Uani 1 1 d . . . C14 C 0.7626(6) 1.0428(5) 0.0992(3) 0.0509(17) Uani 1 1 d . . . H14 H 0.7908 1.0879 0.1315 0.061 Uiso 1 1 calc R . . C15 C 0.7351(8) 1.0691(6) 0.0465(4) 0.074(3) Uani 1 1 d . . . H15 H 0.7456 1.1308 0.0436 0.088 Uiso 1 1 calc R . . C16 C 0.6918(8) 1.0031(6) -0.0017(4) 0.088(3) Uani 1 1 d . . . H16 H 0.6738 1.0203 -0.0374 0.106 Uiso 1 1 calc R . . C17 C 0.6752(8) 0.9109(5) 0.0030(3) 0.073(3) Uani 1 1 d . . . H17 H 0.6441 0.8663 -0.0291 0.087 Uiso 1 1 calc R . . C18 C 0.7054(6) 0.8862(5) 0.0561(3) 0.0463(16) Uani 1 1 d . . . C19 C 0.6823(6) 0.7874(4) 0.0599(3) 0.0443(16) Uani 1 1 d . . . H19 H 0.6349 0.7452 0.0319 0.053 Uiso 1 1 calc R . . C20 C 0.6934(5) 0.6739(4) 0.1155(2) 0.0330(13) Uani 1 1 d . . . C21 C 0.6807(5) 0.5935(4) 0.0765(3) 0.0424(15) Uani 1 1 d . . . H21 H 0.6956 0.5937 0.0376 0.051 Uiso 1 1 calc R . . C22 C 0.6446(5) 0.5109(4) 0.0969(3) 0.0433(15) Uani 1 1 d . . . H22 H 0.6358 0.4551 0.0718 0.052 Uiso 1 1 calc R . . C23 C 0.6225(5) 0.5141(4) 0.1553(3) 0.0365(14) Uani 1 1 d . . . H23 H 0.5983 0.4605 0.1700 0.044 Uiso 1 1 calc R . . C24 C 0.6369(4) 0.5979(4) 0.1909(2) 0.0287(12) Uani 1 1 d . . . C25 C 0.5186(5) 0.5713(4) 0.2606(2) 0.0322(13) Uani 1 1 d . . . H25 H 0.4742 0.5393 0.2275 0.039 Uiso 1 1 calc R . . C26 C 0.4693(4) 0.5764(4) 0.3170(2) 0.0321(13) Uani 1 1 d . . . C27 C 0.3581(5) 0.5594(4) 0.3098(3) 0.0401(15) Uani 1 1 d . . . H27 H 0.3229 0.5414 0.2720 0.048 Uiso 1 1 calc R . . C28 C 0.2996(5) 0.5689(5) 0.3575(3) 0.0472(17) Uani 1 1 d . . . H28 H 0.2256 0.5565 0.3520 0.057 Uiso 1 1 calc R . . C29 C 0.3503(5) 0.5962(5) 0.4126(3) 0.0453(16) Uani 1 1 d . . . H29 H 0.3111 0.6067 0.4446 0.054 Uiso 1 1 calc R . . C30 C 0.4587(5) 0.6086(4) 0.4216(3) 0.0404(15) Uani 1 1 d . . . H30 H 0.4913 0.6241 0.4600 0.048 Uiso 1 1 calc R . . C31 C 0.5220(5) 0.5986(4) 0.3748(3) 0.0323(13) Uani 1 1 d . . . C32 C 0.6495(5) 0.4760(4) 0.4010(2) 0.0333(13) Uani 1 1 d . . . C33 C 0.5536(5) 0.4130(4) 0.3936(3) 0.0426(15) Uani 1 1 d . . . H33 H 0.4908 0.4301 0.3825 0.051 Uiso 1 1 calc R . . C34 C 0.5513(6) 0.3248(5) 0.4026(3) 0.0529(18) Uani 1 1 d . . . H34 H 0.4865 0.2827 0.3975 0.063 Uiso 1 1 calc R . . C35 C 0.6427(6) 0.2979(5) 0.4190(3) 0.0458(16) Uani 1 1 d . . . H35 H 0.6399 0.2380 0.4245 0.055 Uiso 1 1 calc R . . C36 C 0.7383(6) 0.3602(4) 0.4272(3) 0.0420(15) Uani 1 1 d . . . H36 H 0.8006 0.3428 0.4389 0.050 Uiso 1 1 calc R . . C37 C 0.7418(5) 0.4477(4) 0.4180(2) 0.0380(14) Uani 1 1 d . . . H37 H 0.8070 0.4892 0.4232 0.046 Uiso 1 1 calc R . . C38 C 0.7064(5) 0.6593(4) 0.4628(2) 0.0329(13) Uani 1 1 d . . . C39 C 0.6936(5) 0.6215(5) 0.5142(3) 0.0424(15) Uani 1 1 d . . . H39 H 0.6560 0.5616 0.5119 0.051 Uiso 1 1 calc R . . C40 C 0.7364(6) 0.6727(6) 0.5688(3) 0.0531(18) Uani 1 1 d . . . H40 H 0.7265 0.6465 0.6025 0.064 Uiso 1 1 calc R . . C41 C 0.7918(6) 0.7593(6) 0.5737(3) 0.0571(19) Uani 1 1 d . . . H41 H 0.8206 0.7923 0.6105 0.068 Uiso 1 1 calc R . . C42 C 0.8059(7) 0.7996(6) 0.5228(3) 0.065(2) Uani 1 1 d . . . H42 H 0.8436 0.8596 0.5258 0.078 Uiso 1 1 calc R . . C43 C 0.7632(6) 0.7493(5) 0.4686(3) 0.0488(17) Uani 1 1 d . . . H43 H 0.7726 0.7761 0.4350 0.059 Uiso 1 1 calc R . . C44 C 0.8096(4) 0.4373(4) 0.2378(2) 0.0318(12) Uani 1 1 d . . . C45 C 0.7183(5) 0.3879(4) 0.2581(3) 0.0398(14) Uani 1 1 d . . . H45 H 0.6948 0.4118 0.2933 0.048 Uiso 1 1 calc R . . C46 C 0.6634(6) 0.3054(4) 0.2273(3) 0.0487(17) Uani 1 1 d . . . H46 H 0.6034 0.2737 0.2416 0.058 Uiso 1 1 calc R . . C47 C 0.6978(6) 0.2688(5) 0.1741(4) 0.062(2) Uani 1 1 d . . . H47 H 0.6602 0.2133 0.1526 0.074 Uiso 1 1 calc R . . C48 C 0.7870(7) 0.3154(5) 0.1541(4) 0.066(2) Uani 1 1 d . . . H48 H 0.8106 0.2906 0.1192 0.080 Uiso 1 1 calc R . . C49 C 0.8428(6) 0.3987(5) 0.1848(3) 0.0534(18) Uani 1 1 d . . . H49 H 0.9030 0.4295 0.1701 0.064 Uiso 1 1 calc R . . C50 C 0.9645(5) 0.5940(4) 0.2286(2) 0.0349(13) Uani 1 1 d . . . C51 C 1.0543(5) 0.5612(5) 0.2194(3) 0.0442(15) Uani 1 1 d . . . H51 H 1.0747 0.5224 0.2434 0.053 Uiso 1 1 calc R . . C52 C 1.1158(6) 0.5854(6) 0.1742(3) 0.059(2) Uani 1 1 d . . . H52 H 1.1772 0.5631 0.1683 0.070 Uiso 1 1 calc R . . C53 C 1.0854(7) 0.6423(6) 0.1385(4) 0.067(2) Uani 1 1 d . . . H53 H 1.1237 0.6564 0.1070 0.080 Uiso 1 1 calc R . . C54 C 0.9961(7) 0.6788(6) 0.1502(3) 0.062(2) Uani 1 1 d . . . H54 H 0.9769 0.7197 0.1274 0.075 Uiso 1 1 calc R . . C55 C 0.9363(6) 0.6548(5) 0.1949(3) 0.0460(16) Uani 1 1 d . . . H55 H 0.8770 0.6795 0.2024 0.055 Uiso 1 1 calc R . . C56 C 0.9573(4) 0.5245(4) 0.3389(2) 0.0310(12) Uani 1 1 d . . . C57 C 0.9715(5) 0.4362(4) 0.3391(3) 0.0376(14) Uani 1 1 d . . . H57 H 0.9422 0.3911 0.3070 0.045 Uiso 1 1 calc R . . C58 C 1.0276(5) 0.4129(4) 0.3853(3) 0.0427(15) Uani 1 1 d . . . H58 H 1.0358 0.3531 0.3839 0.051 Uiso 1 1 calc R . . C59 C 1.0717(5) 0.4789(4) 0.4338(3) 0.0402(15) Uani 1 1 d . . . H59 H 1.1092 0.4631 0.4651 0.048 Uiso 1 1 calc R . . C60 C 1.0600(5) 0.5673(4) 0.4358(3) 0.0384(14) Uani 1 1 d . . . H60 H 1.0884 0.6109 0.4688 0.046 Uiso 1 1 calc R . . C61 C 1.0055(4) 0.5927(4) 0.3882(2) 0.0314(12) Uani 1 1 d . . . C62 C 0.9886(5) 0.6856(4) 0.3937(3) 0.0339(13) Uani 1 1 d . . . H62 H 1.0029 0.7245 0.4299 0.041 Uiso 1 1 calc R . . C63 C 0.9142(5) 0.7929(4) 0.3528(2) 0.0337(13) Uani 1 1 d . . . C64 C 0.9686(5) 0.8776(4) 0.3823(3) 0.0413(15) Uani 1 1 d . . . H64 H 1.0383 0.8866 0.3991 0.050 Uiso 1 1 calc R . . C65 C 0.9148(6) 0.9492(4) 0.3859(3) 0.0471(16) Uani 1 1 d . . . H65 H 0.9478 1.0069 0.4062 0.057 Uiso 1 1 calc R . . C66 C 0.8116(5) 0.9341(4) 0.3591(3) 0.0409(15) Uani 1 1 d . . . H66 H 0.7745 0.9810 0.3615 0.049 Uiso 1 1 calc R . . C67 C 0.7654(5) 0.8475(4) 0.3287(2) 0.0309(12) Uani 1 1 d . . . C68 C 0.5837(5) 0.8331(4) 0.3305(3) 0.0373(14) Uani 1 1 d . . . H68 H 0.6027 0.8535 0.3707 0.045 Uiso 1 1 calc R . . C69 C 0.4685(5) 0.8130(4) 0.3113(3) 0.0359(14) Uani 1 1 d . . . C70 C 0.4045(5) 0.8050(5) 0.3583(3) 0.0453(16) Uani 1 1 d . . . H70 H 0.4373 0.8160 0.3966 0.054 Uiso 1 1 calc R . . C71 C 0.2959(6) 0.7816(5) 0.3496(3) 0.0517(18) Uani 1 1 d . . . H71 H 0.2557 0.7776 0.3816 0.062 Uiso 1 1 calc R . . C72 C 0.2463(6) 0.7641(5) 0.2932(3) 0.0482(17) Uani 1 1 d . . . H72 H 0.1725 0.7461 0.2866 0.058 Uiso 1 1 calc R . . C73 C 0.3086(5) 0.7737(4) 0.2461(3) 0.0398(14) Uani 1 1 d . . . H73 H 0.2749 0.7632 0.2081 0.048 Uiso 1 1 calc R . . C74 C 0.4182(5) 0.7983(4) 0.2540(3) 0.0340(13) Uani 1 1 d . . . C75 C 0.4059(4) 0.7516(4) 0.1272(2) 0.0329(13) Uani 1 1 d . . . C76 C 0.4100(6) 0.6598(5) 0.1151(3) 0.0500(17) Uani 1 1 d . . . H76 H 0.4543 0.6368 0.1396 0.060 Uiso 1 1 calc R . . C77 C 0.3493(6) 0.6017(5) 0.0673(4) 0.063(2) Uani 1 1 d . . . H77 H 0.3531 0.5404 0.0606 0.076 Uiso 1 1 calc R . . C78 C 0.2847(6) 0.6325(6) 0.0304(3) 0.056(2) Uani 1 1 d . . . H78 H 0.2446 0.5932 -0.0018 0.068 Uiso 1 1 calc R . . C79 C 0.2795(6) 0.7250(6) 0.0416(3) 0.058(2) Uani 1 1 d . . . H79 H 0.2347 0.7471 0.0169 0.069 Uiso 1 1 calc R . . C80 C 0.3395(5) 0.7832(5) 0.0885(3) 0.0446(16) Uani 1 1 d . . . H80 H 0.3361 0.8446 0.0948 0.053 Uiso 1 1 calc R . . C81 C 0.4653(5) 0.9387(4) 0.1869(3) 0.0404(15) Uani 1 1 d . . . C82 C 0.4258(5) 0.9893(4) 0.2317(3) 0.0503(17) Uani 1 1 d . . . H82 H 0.4074 0.9646 0.2651 0.060 Uiso 1 1 calc R . . C83 C 0.4129(7) 1.0787(5) 0.2273(5) 0.070(2) Uani 1 1 d . . . H83 H 0.3856 1.1122 0.2576 0.085 Uiso 1 1 calc R . . C84 C 0.4404(7) 1.1159(6) 0.1787(5) 0.078(3) Uani 1 1 d . . . H84 H 0.4318 1.1747 0.1761 0.093 Uiso 1 1 calc R . . C85 C 0.4809(6) 1.0669(5) 0.1337(4) 0.065(2) Uani 1 1 d . . . H85 H 0.4987 1.0923 0.1004 0.078 Uiso 1 1 calc R . . C86 C 0.4953(5) 0.9784(5) 0.1377(3) 0.0516(18) Uani 1 1 d . . . H86 H 0.5249 0.9461 0.1078 0.062 Uiso 1 1 calc R . . C87 C 0.3509(12) 0.0228(11) 0.4376(7) 0.136(5) Uani 1 1 d . . . Cu1 Cu 0.66013(5) 0.81200(5) 0.20735(3) 0.0300(2) Uani 1 1 d . . . Cu2 Cu 0.74889(5) 0.63429(4) 0.31156(3) 0.0281(2) Uani 1 1 d . . . N1 N 0.7289(4) 0.7621(3) 0.1025(2) 0.0356(11) Uani 1 1 d . . . N2 N 0.6727(4) 0.6777(3) 0.17339(18) 0.0274(10) Uani 1 1 d . . . N3 N 0.6149(4) 0.6055(3) 0.25137(18) 0.0265(10) Uani 1 1 d . . . N4 N 0.9541(4) 0.7127(3) 0.3483(2) 0.0296(10) Uani 1 1 d . . . N5 N 0.8157(4) 0.7770(3) 0.32521(19) 0.0278(10) Uani 1 1 d . . . N6 N 0.6615(4) 0.8257(3) 0.29828(19) 0.0305(10) Uani 1 1 d . . . P1 P 0.78513(12) 0.92368(10) 0.17806(6) 0.0316(3) Uani 1 1 d . . . P2 P 0.66220(12) 0.59493(10) 0.38891(6) 0.0297(3) Uani 1 1 d . . . P3 P 0.87116(11) 0.55065(10) 0.27961(6) 0.0279(3) Uani 1 1 d . . . P4 P 0.49009(12) 0.82483(10) 0.19013(6) 0.0313(3) Uani 1 1 d . . . B1 B 0.8239(11) 0.1466(8) 0.4830(6) 0.094(3) Uani 1 1 d . . . B2 B 0.3778(12) 0.3408(8) 0.1020(6) 0.094(3) Uani 1 1 d . . . F1 F 0.9025(8) 0.1964(7) 0.4615(4) 0.169(3) Uiso 1 1 d . . . F2 F 0.7894(5) 0.2104(5) 0.5211(3) 0.114(2) Uiso 1 1 d . . . F3 F 0.8442(7) 0.0801(6) 0.5121(4) 0.149(3) Uiso 1 1 d . . . F4 F 0.7423(5) 0.1068(4) 0.4392(2) 0.0932(16) Uiso 1 1 d . . . F5 F 0.3732(8) 0.4103(7) 0.1478(4) 0.171(3) Uiso 1 1 d . . . F6 F 0.4735(12) 0.3052(10) 0.0961(6) 0.243(6) Uiso 1 1 d . . . F7 F 0.3059(7) 0.2591(6) 0.0970(4) 0.144(3) Uiso 1 1 d . . . F8 F 0.3939(8) 0.3848(7) 0.0588(4) 0.170(3) Uiso 1 1 d . . . Cl1 Cl 0.2768(4) 0.0216(3) 0.3723(2) 0.1145(13) Uiso 0.75 1 d P A 1 Cl1' Cl 0.3533(16) 0.0580(13) 0.3748(8) 0.145(5) Uiso 0.25 1 d P A 2 Cl2 Cl 0.4866(7) 0.0546(6) 0.4278(4) 0.149(2) Uiso 0.55 1 d P A 3 Cl2' Cl 0.4495(8) 0.1260(6) 0.4843(4) 0.143(3) Uiso 0.45 1 d P A 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(3) 0.034(3) 0.042(3) 0.004(3) 0.006(3) 0.004(3) C2 0.044(4) 0.052(4) 0.053(4) 0.010(3) 0.005(3) 0.016(3) C3 0.043(4) 0.066(5) 0.081(6) 0.008(4) -0.010(4) 0.021(4) C4 0.033(4) 0.082(6) 0.107(7) 0.012(5) 0.013(5) 0.018(4) C5 0.051(5) 0.109(8) 0.098(7) 0.033(6) 0.037(5) 0.026(5) C6 0.045(4) 0.077(5) 0.054(4) 0.019(4) 0.016(3) 0.016(4) C7 0.042(4) 0.027(3) 0.036(3) 0.008(3) 0.003(3) 0.008(3) C8 0.053(4) 0.039(4) 0.065(5) 0.004(3) 0.010(4) 0.003(3) C9 0.069(5) 0.047(4) 0.069(5) -0.018(4) 0.017(4) -0.005(4) C10 0.069(5) 0.040(4) 0.059(5) -0.003(3) 0.011(4) 0.009(4) C11 0.049(4) 0.042(4) 0.053(4) 0.008(3) 0.006(3) 0.017(3) C12 0.049(4) 0.037(3) 0.043(4) 0.008(3) 0.005(3) 0.013(3) C13 0.041(3) 0.037(3) 0.030(3) 0.011(3) 0.003(3) 0.004(3) C14 0.063(5) 0.038(4) 0.047(4) 0.011(3) -0.011(3) 0.002(3) C15 0.101(7) 0.045(4) 0.065(5) 0.024(4) -0.026(5) -0.008(4) C16 0.124(8) 0.068(6) 0.061(5) 0.036(5) -0.044(5) -0.011(5) C17 0.115(7) 0.047(5) 0.042(4) 0.008(4) -0.020(4) -0.005(5) C18 0.057(4) 0.042(4) 0.040(4) 0.016(3) 0.003(3) 0.005(3) C19 0.064(4) 0.041(4) 0.024(3) 0.005(3) -0.002(3) 0.006(3) C20 0.033(3) 0.035(3) 0.031(3) 0.005(3) 0.006(2) 0.005(3) C21 0.056(4) 0.042(4) 0.029(3) -0.001(3) 0.013(3) 0.010(3) C22 0.059(4) 0.035(3) 0.033(3) -0.005(3) 0.009(3) 0.010(3) C23 0.046(4) 0.030(3) 0.033(3) 0.003(3) 0.006(3) 0.008(3) C24 0.030(3) 0.033(3) 0.024(3) 0.004(2) 0.002(2) 0.012(2) C25 0.029(3) 0.035(3) 0.032(3) 0.005(3) -0.002(2) 0.009(3) C26 0.031(3) 0.037(3) 0.034(3) 0.008(3) 0.009(2) 0.016(3) C27 0.035(3) 0.047(4) 0.043(4) 0.018(3) 0.005(3) 0.012(3) C28 0.036(4) 0.061(4) 0.053(4) 0.020(4) 0.016(3) 0.019(3) C29 0.041(4) 0.060(4) 0.044(4) 0.017(3) 0.021(3) 0.023(3) C30 0.045(4) 0.045(4) 0.036(3) 0.012(3) 0.011(3) 0.015(3) C31 0.034(3) 0.029(3) 0.037(3) 0.008(3) 0.008(3) 0.010(2) C32 0.035(3) 0.038(3) 0.027(3) 0.001(2) 0.006(2) 0.010(3) C33 0.038(4) 0.038(4) 0.059(4) 0.016(3) 0.010(3) 0.015(3) C34 0.051(4) 0.040(4) 0.069(5) 0.017(4) 0.008(4) 0.005(3) C35 0.056(4) 0.039(4) 0.049(4) 0.008(3) 0.012(3) 0.021(3) C36 0.051(4) 0.048(4) 0.033(3) 0.008(3) 0.005(3) 0.024(3) C37 0.039(3) 0.049(4) 0.029(3) 0.007(3) 0.008(3) 0.013(3) C38 0.035(3) 0.036(3) 0.030(3) 0.002(3) 0.004(2) 0.015(3) C39 0.050(4) 0.051(4) 0.029(3) 0.007(3) 0.004(3) 0.019(3) C40 0.061(5) 0.073(5) 0.032(4) 0.010(3) 0.004(3) 0.030(4) C41 0.062(5) 0.074(6) 0.029(4) -0.010(4) -0.004(3) 0.019(4) C42 0.078(6) 0.062(5) 0.042(4) -0.011(4) 0.003(4) -0.003(4) C43 0.062(5) 0.048(4) 0.035(4) 0.003(3) 0.011(3) 0.010(3) C44 0.031(3) 0.029(3) 0.033(3) 0.002(2) -0.003(2) 0.007(2) C45 0.038(3) 0.042(4) 0.040(3) 0.005(3) 0.004(3) 0.011(3) C46 0.044(4) 0.037(4) 0.060(4) 0.006(3) 0.003(3) 0.002(3) C47 0.053(5) 0.047(4) 0.074(5) -0.017(4) 0.005(4) 0.007(4) C48 0.067(5) 0.057(5) 0.064(5) -0.021(4) 0.018(4) 0.007(4) C49 0.049(4) 0.048(4) 0.054(4) -0.013(3) 0.011(3) 0.002(3) C50 0.033(3) 0.037(3) 0.031(3) -0.002(3) 0.001(2) 0.005(3) C51 0.033(3) 0.049(4) 0.049(4) 0.002(3) 0.012(3) 0.007(3) C52 0.041(4) 0.065(5) 0.063(5) -0.008(4) 0.022(4) 0.004(4) C53 0.066(5) 0.068(5) 0.062(5) 0.008(4) 0.036(4) -0.003(4) C54 0.074(6) 0.067(5) 0.050(4) 0.024(4) 0.018(4) 0.009(4) C55 0.052(4) 0.044(4) 0.045(4) 0.011(3) 0.017(3) 0.011(3) C56 0.030(3) 0.031(3) 0.035(3) 0.007(3) 0.008(2) 0.010(2) C57 0.039(3) 0.041(3) 0.036(3) 0.005(3) 0.005(3) 0.016(3) C58 0.045(4) 0.038(3) 0.050(4) 0.008(3) 0.006(3) 0.020(3) C59 0.038(3) 0.051(4) 0.037(3) 0.011(3) -0.003(3) 0.022(3) C60 0.040(4) 0.047(4) 0.029(3) 0.005(3) 0.004(3) 0.012(3) C61 0.028(3) 0.035(3) 0.032(3) 0.004(3) 0.007(2) 0.009(2) C62 0.033(3) 0.035(3) 0.031(3) 0.000(3) 0.003(2) 0.007(3) C63 0.034(3) 0.032(3) 0.033(3) 0.004(3) 0.004(3) 0.003(3) C64 0.049(4) 0.036(3) 0.035(3) 0.001(3) -0.005(3) 0.008(3) C65 0.064(5) 0.033(3) 0.039(4) -0.002(3) -0.011(3) 0.009(3) C66 0.053(4) 0.032(3) 0.038(3) 0.003(3) 0.002(3) 0.014(3) C67 0.041(3) 0.033(3) 0.020(3) 0.002(2) 0.000(2) 0.013(3) C68 0.047(4) 0.036(3) 0.033(3) 0.005(3) 0.007(3) 0.018(3) C69 0.041(3) 0.035(3) 0.035(3) 0.004(3) 0.010(3) 0.014(3) C70 0.050(4) 0.053(4) 0.037(3) 0.002(3) 0.013(3) 0.023(3) C71 0.046(4) 0.060(5) 0.057(4) 0.015(4) 0.026(3) 0.021(3) C72 0.042(4) 0.045(4) 0.057(4) 0.001(3) 0.018(3) 0.009(3) C73 0.036(3) 0.043(4) 0.041(4) 0.005(3) 0.007(3) 0.010(3) C74 0.035(3) 0.033(3) 0.037(3) 0.006(3) 0.008(3) 0.012(3) C75 0.030(3) 0.039(3) 0.031(3) 0.010(3) 0.004(2) 0.007(3) C76 0.051(4) 0.047(4) 0.053(4) 0.003(3) -0.004(3) 0.019(3) C77 0.053(5) 0.052(4) 0.075(5) -0.022(4) 0.003(4) 0.014(4) C78 0.048(4) 0.076(6) 0.035(4) -0.013(4) 0.007(3) 0.007(4) C79 0.049(4) 0.079(6) 0.042(4) 0.022(4) -0.001(3) -0.001(4) C80 0.041(4) 0.047(4) 0.043(4) 0.012(3) 0.000(3) 0.000(3) C81 0.034(3) 0.032(3) 0.053(4) 0.006(3) -0.006(3) 0.005(3) C82 0.047(4) 0.032(3) 0.075(5) 0.010(3) 0.005(4) 0.014(3) C83 0.058(5) 0.039(4) 0.114(7) 0.005(5) 0.002(5) 0.019(4) C84 0.059(5) 0.036(4) 0.137(9) 0.030(6) -0.023(5) 0.007(4) C85 0.056(5) 0.040(4) 0.090(6) 0.028(4) -0.027(4) -0.010(4) C86 0.047(4) 0.040(4) 0.064(5) 0.021(4) -0.016(3) -0.002(3) C87 0.133(12) 0.144(12) 0.135(12) 0.034(10) 0.006(9) 0.030(10) Cu1 0.0337(4) 0.0299(4) 0.0275(4) 0.0041(3) 0.0040(3) 0.0097(3) Cu2 0.0284(4) 0.0297(4) 0.0272(4) 0.0036(3) 0.0051(3) 0.0085(3) N1 0.049(3) 0.034(3) 0.025(2) 0.006(2) 0.009(2) 0.007(2) N2 0.032(3) 0.029(2) 0.024(2) 0.0049(19) 0.0043(19) 0.010(2) N3 0.032(3) 0.026(2) 0.024(2) 0.0054(19) 0.0038(19) 0.011(2) N4 0.027(2) 0.028(2) 0.030(2) 0.001(2) -0.0028(19) 0.003(2) N5 0.034(3) 0.027(2) 0.025(2) 0.0026(19) 0.0035(19) 0.012(2) N6 0.042(3) 0.025(2) 0.028(2) 0.0037(19) 0.004(2) 0.014(2) P1 0.0369(9) 0.0303(8) 0.0279(8) 0.0055(6) 0.0025(6) 0.0075(6) P2 0.0315(8) 0.0339(8) 0.0265(7) 0.0069(6) 0.0072(6) 0.0111(6) P3 0.0272(7) 0.0294(8) 0.0276(7) 0.0019(6) 0.0049(6) 0.0086(6) P4 0.0324(8) 0.0303(8) 0.0328(8) 0.0066(6) 0.0024(6) 0.0093(6) B1 0.116(7) 0.061(5) 0.085(5) -0.009(4) 0.036(5) -0.021(5) B2 0.116(7) 0.061(5) 0.085(5) -0.009(4) 0.036(5) -0.021(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 C1 C6 1.390(9) . ? C1 C2 1.396(9) . ? C1 P1 1.819(6) . ? C2 C3 1.392(10) . ? C2 H2 0.9300 . ? C3 C4 1.378(12) . ? C3 H3 0.9300 . ? C4 C5 1.372(13) . ? C4 H4 0.9300 . ? C5 C6 1.380(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.382(9) . ? C7 C8 1.405(9) . ? C7 P1 1.829(6) . ? C8 C9 1.384(10) . ? C8 H8 0.9300 . ? C9 C10 1.382(11) . ? C9 H9 0.9300 . ? C10 C11 1.367(10) . ? C10 H10 0.9300 . ? C11 C12 1.385(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.383(9) . ? C13 C18 1.406(9) . ? C13 P1 1.835(6) . ? C14 C15 1.384(10) . ? C14 H14 0.9300 . ? C15 C16 1.380(12) . ? C15 H15 0.9300 . ? C16 C17 1.392(11) . ? C16 H16 0.9300 . ? C17 C18 1.390(9) . ? C17 H17 0.9300 . ? C18 C19 1.483(9) . ? C19 N1 1.267(8) . ? C19 H19 0.9300 . ? C20 C21 1.372(8) . ? C20 N2 1.372(7) . ? C20 N1 1.406(7) . ? C21 C22 1.404(9) . ? C21 H21 0.9300 . ? C22 C23 1.388(8) . ? C22 H22 0.9300 . ? C23 C24 1.374(8) . ? C23 H23 0.9300 . ? C24 N2 1.335(7) . ? C24 N3 1.431(7) . ? C25 N3 1.287(7) . ? C25 C26 1.478(8) . ? C25 H25 0.9300 . ? C26 C27 1.397(8) . ? C26 C31 1.417(8) . ? C27 C28 1.377(9) . ? C27 H27 0.9300 . ? C28 C29 1.357(10) . ? C28 H28 0.9300 . ? C29 C30 1.367(9) . ? C29 H29 0.9300 . ? C30 C31 1.402(8) . ? C30 H30 0.9300 . ? C31 P2 1.827(6) . ? C32 C33 1.382(9) . ? C32 C37 1.397(8) . ? C32 P2 1.840(6) . ? C33 C34 1.378(9) . ? C33 H33 0.9300 . ? C34 C35 1.370(10) . ? C34 H34 0.9300 . ? C35 C36 1.374(10) . ? C35 H35 0.9300 . ? C36 C37 1.365(9) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 C43 1.392(9) . ? C38 C39 1.398(8) . ? C38 P2 1.823(6) . ? C39 C40 1.388(9) . ? C39 H39 0.9300 . ? C40 C41 1.345(11) . ? C40 H40 0.9300 . ? C41 C42 1.407(11) . ? C41 H41 0.9300 . ? C42 C43 1.379(10) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C44 C45 1.406(8) . ? C44 C49 1.402(9) . ? C44 P3 1.832(6) . ? C45 C46 1.370(9) . ? C45 H45 0.9300 . ? C46 C47 1.401(10) . ? C46 H46 0.9300 . ? C47 C48 1.366(11) . ? C47 H47 0.9300 . ? C48 C49 1.380(10) . ? C48 H48 0.9300 . ? C49 H49 0.9300 . ? C50 C51 1.364(9) . ? C50 C55 1.379(9) . ? C50 P3 1.829(6) . ? C51 C52 1.395(9) . ? C51 H51 0.9300 . ? C52 C53 1.373(12) . ? C52 H52 0.9300 . ? C53 C54 1.395(12) . ? C53 H53 0.9300 . ? C54 C55 1.373(9) . ? C54 H54 0.9300 . ? C55 H55 0.9300 . ? C56 C57 1.386(8) . ? C56 C61 1.427(8) . ? C56 P3 1.847(6) . ? C57 C58 1.379(8) . ? C57 H57 0.9300 . ? C58 C59 1.386(9) . ? C58 H58 0.9300 . ? C59 C60 1.371(9) . ? C59 H59 0.9300 . ? C60 C61 1.410(8) . ? C60 H60 0.9300 . ? C61 C62 1.455(8) . ? C62 N4 1.269(7) . ? C62 H62 0.9300 . ? C63 N5 1.341(7) . ? C63 C64 1.383(9) . ? C63 N4 1.403(7) . ? C64 C65 1.394(9) . ? C64 H64 0.9300 . ? C65 C66 1.389(9) . ? C65 H65 0.9300 . ? C66 C67 1.384(8) . ? C66 H66 0.9300 . ? C67 N5 1.351(7) . ? C67 N6 1.423(7) . ? C68 N6 1.296(7) . ? C68 C69 1.477(9) . ? C68 H68 0.9300 . ? C69 C74 1.400(8) . ? C69 C70 1.405(8) . ? C70 C71 1.365(10) . ? C70 H70 0.9300 . ? C71 C72 1.375(10) . ? C71 H71 0.9300 . ? C72 C73 1.397(9) . ? C72 H72 0.9300 . ? C73 C74 1.378(8) . ? C73 H73 0.9300 . ? C74 P4 1.840(6) . ? C75 C80 1.399(8) . ? C75 C76 1.389(9) . ? C75 P4 1.826(6) . ? C76 C77 1.384(10) . ? C76 H76 0.9300 . ? C77 C78 1.351(11) . ? C77 H77 0.9300 . ? C78 C79 1.401(11) . ? C78 H78 0.9300 . ? C79 C80 1.368(10) . ? C79 H79 0.9300 . ? C80 H80 0.9300 . ? C81 C82 1.376(9) . ? C81 C86 1.400(9) . ? C81 P4 1.828(6) . ? C82 C83 1.415(10) . ? C82 H82 0.9300 . ? C83 C84 1.362(13) . ? C83 H83 0.9300 . ? C84 C85 1.374(13) . ? C84 H84 0.9300 . ? C85 C86 1.407(10) . ? C85 H85 0.9300 . ? C86 H86 0.9300 . ? C87 Cl1' 1.62(2) . ? C87 Cl1 1.727(15) . ? C87 Cl2 1.753(17) . ? C87 Cl2' 1.931(18) . ? Cu1 N6 2.073(4) . ? Cu1 N2 2.108(4) . ? Cu1 P4 2.2524(16) . ? Cu1 P1 2.2993(16) . ? Cu2 N3 2.075(4) . ? Cu2 N5 2.126(4) . ? Cu2 P2 2.2539(15) . ? Cu2 P3 2.2995(15) . ? B1 F2 1.364(13) . ? B1 F3 1.349(15) . ? B1 F4 1.385(14) . ? B1 F1 1.305(13) . ? B2 F8 1.285(14) . ? B2 F5 1.387(14) . ? B2 F6 1.447(18) . ? B2 F7 1.372(13) . ? 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 C1 C2 118.1(6) . . ? C6 C1 P1 123.9(5) . . ? C2 C1 P1 117.7(5) . . ? C3 C2 C1 121.1(7) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C4 C3 C2 119.9(7) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.0(7) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.8(8) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 120.0(7) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C12 C7 C8 118.0(6) . . ? C12 C7 P1 117.5(5) . . ? C8 C7 P1 124.3(5) . . ? C9 C8 C7 120.3(7) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.1(7) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.2(7) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.0(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 121.3(6) . . ? C7 C12 H12 119.4 . . ? C11 C12 H12 119.3 . . ? C14 C13 C18 116.7(5) . . ? C14 C13 P1 119.6(5) . . ? C18 C13 P1 123.6(4) . . ? C15 C14 C13 122.7(7) . . ? C15 C14 H14 118.6 . . ? C13 C14 H14 118.6 . . ? C14 C15 C16 119.4(7) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.1(7) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 119.3(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C13 121.7(6) . . ? C17 C18 C19 117.5(6) . . ? C13 C18 C19 120.6(5) . . ? N1 C19 C18 118.0(6) . . ? N1 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? C21 C20 N2 123.3(5) . . ? C21 C20 N1 125.7(5) . . ? N2 C20 N1 111.0(5) . . ? C20 C21 C22 118.4(5) . . ? C20 C21 H21 120.8 . . ? C22 C21 H21 120.8 . . ? C23 C22 C21 118.7(6) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C24 C23 C22 118.8(6) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? N2 C24 C23 124.1(5) . . ? N2 C24 N3 114.6(5) . . ? C23 C24 N3 121.3(5) . . ? N3 C25 C26 128.5(5) . . ? N3 C25 H25 115.8 . . ? C26 C25 H25 115.8 . . ? C27 C26 C31 119.1(5) . . ? C27 C26 C25 113.4(5) . . ? C31 C26 C25 127.5(5) . . ? C28 C27 C26 121.2(6) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C29 C28 C27 119.8(6) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.6(6) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C31 122.0(6) . . ? C29 C30 H30 119.0 . . ? C31 C30 H30 119.0 . . ? C30 C31 C26 117.2(5) . . ? C30 C31 P2 120.4(5) . . ? C26 C31 P2 121.6(4) . . ? C33 C32 C37 118.2(6) . . ? C33 C32 P2 123.5(5) . . ? C37 C32 P2 118.2(5) . . ? C32 C33 C34 119.8(6) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 121.2(7) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C34 C35 C36 119.5(6) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C37 C36 C35 119.9(6) . . ? C37 C36 H36 120.1 . . ? C35 C36 H36 120.1 . . ? C36 C37 C32 121.3(6) . . ? C36 C37 H37 119.3 . . ? C32 C37 H37 119.3 . . ? C43 C38 C39 117.5(6) . . ? C43 C38 P2 118.6(4) . . ? C39 C38 P2 123.7(5) . . ? C40 C39 C38 120.6(7) . . ? C40 C39 H39 119.7 . . ? C38 C39 H39 119.7 . . ? C41 C40 C39 121.3(6) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C40 C41 C42 119.7(7) . . ? C40 C41 H41 120.2 . . ? C42 C41 H41 120.2 . . ? C43 C42 C41 119.3(7) . . ? C43 C42 H42 120.3 . . ? C41 C42 H42 120.3 . . ? C42 C43 C38 121.6(6) . . ? C42 C43 H43 119.2 . . ? C38 C43 H43 119.2 . . ? C45 C44 C49 117.5(6) . . ? C45 C44 P3 117.8(4) . . ? C49 C44 P3 124.6(5) . . ? C46 C45 C44 121.5(6) . . ? C46 C45 H45 119.3 . . ? C44 C45 H45 119.3 . . ? C45 C46 C47 119.8(7) . . ? C45 C46 H46 120.1 . . ? C47 C46 H46 120.1 . . ? C48 C47 C46 119.5(7) . . ? C48 C47 H47 120.3 . . ? C46 C47 H47 120.3 . . ? C47 C48 C49 121.1(7) . . ? C47 C48 H48 119.4 . . ? C49 C48 H48 119.4 . . ? C48 C49 C44 120.6(7) . . ? C48 C49 H49 119.7 . . ? C44 C49 H49 119.7 . . ? C51 C50 C55 120.1(6) . . ? C51 C50 P3 121.7(5) . . ? C55 C50 P3 117.9(5) . . ? C50 C51 C52 120.5(7) . . ? C50 C51 H51 119.8 . . ? C52 C51 H51 119.8 . . ? C53 C52 C51 119.8(7) . . ? C53 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? C54 C53 C52 119.1(6) . . ? C54 C53 H53 120.5 . . ? C52 C53 H53 120.5 . . ? C53 C54 C55 120.7(7) . . ? C53 C54 H54 119.7 . . ? C55 C54 H54 119.7 . . ? C50 C55 C54 119.8(7) . . ? C50 C55 H55 120.1 . . ? C54 C55 H55 120.1 . . ? C57 C56 C61 117.6(5) . . ? C57 C56 P3 121.0(5) . . ? C61 C56 P3 121.3(4) . . ? C58 C57 C56 122.3(6) . . ? C58 C57 H57 118.8 . . ? C56 C57 H57 118.8 . . ? C59 C58 C57 119.9(6) . . ? C59 C58 H58 120.0 . . ? C57 C58 H58 120.0 . . ? C58 C59 C60 120.1(5) . . ? C58 C59 H59 120.0 . . ? C60 C59 H59 120.0 . . ? C59 C60 C61 120.6(6) . . ? C59 C60 H60 119.7 . . ? C61 C60 H60 119.7 . . ? C60 C61 C56 119.4(5) . . ? C60 C61 C62 118.8(5) . . ? C56 C61 C62 121.3(5) . . ? N4 C62 C61 118.9(5) . . ? N4 C62 H62 120.6 . . ? C61 C62 H62 120.6 . . ? N5 C63 C64 123.9(6) . . ? N5 C63 N4 111.5(5) . . ? C64 C63 N4 124.6(5) . . ? C63 C64 C65 117.4(6) . . ? C63 C64 H64 121.3 . . ? C65 C64 H64 121.3 . . ? C66 C65 C64 119.9(6) . . ? C66 C65 H65 120.1 . . ? C64 C65 H65 120.1 . . ? C67 C66 C65 118.5(6) . . ? C67 C66 H66 120.8 . . ? C65 C66 H66 120.8 . . ? N5 C67 C66 122.6(5) . . ? N5 C67 N6 114.6(5) . . ? C66 C67 N6 122.8(5) . . ? N6 C68 C69 127.9(6) . . ? N6 C68 H68 116.1 . . ? C69 C68 H68 116.1 . . ? C74 C69 C70 118.4(6) . . ? C74 C69 C68 128.7(5) . . ? C70 C69 C68 112.9(5) . . ? C71 C70 C69 122.2(6) . . ? C71 C70 H70 118.9 . . ? C69 C70 H70 118.9 . . ? C72 C71 C70 119.6(6) . . ? C72 C71 H71 120.2 . . ? C70 C71 H71 120.2 . . ? C71 C72 C73 118.9(6) . . ? C71 C72 H72 120.5 . . ? C73 C72 H72 120.5 . . ? C74 C73 C72 122.3(6) . . ? C74 C73 H73 118.8 . . ? C72 C73 H73 118.8 . . ? C73 C74 C69 118.5(5) . . ? C73 C74 P4 118.1(5) . . ? C69 C74 P4 122.9(5) . . ? C80 C75 C76 117.2(6) . . ? C80 C75 P4 123.8(5) . . ? C76 C75 P4 119.0(5) . . ? C77 C76 C75 121.2(7) . . ? C77 C76 H76 119.4 . . ? C75 C76 H76 119.4 . . ? C78 C77 C76 121.3(7) . . ? C78 C77 H77 119.4 . . ? C76 C77 H77 119.4 . . ? C77 C78 C79 118.5(7) . . ? C77 C78 H78 120.8 . . ? C79 C78 H78 120.8 . . ? C80 C79 C78 120.8(7) . . ? C80 C79 H79 119.6 . . ? C78 C79 H79 119.6 . . ? C79 C80 C75 121.0(7) . . ? C79 C80 H80 119.5 . . ? C75 C80 H80 119.5 . . ? C82 C81 C86 118.7(6) . . ? C82 C81 P4 123.5(5) . . ? C86 C81 P4 117.6(5) . . ? C81 C82 C83 120.5(7) . . ? C81 C82 H82 119.8 . . ? C83 C82 H82 119.8 . . ? C84 C83 C82 120.3(9) . . ? C84 C83 H83 119.9 . . ? C82 C83 H83 119.9 . . ? C85 C84 C83 120.3(7) . . ? C85 C84 H84 119.9 . . ? C83 C84 H84 119.9 . . ? C84 C85 C86 120.1(8) . . ? C84 C85 H85 119.9 . . ? C86 C85 H85 119.9 . . ? C85 C86 C81 120.1(8) . . ? C85 C86 H86 120.0 . . ? C81 C86 H86 119.9 . . ? Cl1' C87 Cl1 35.3(7) . . ? Cl1' C87 Cl2 75.1(10) . . ? Cl1 C87 Cl2 108.8(9) . . ? Cl1' C87 Cl2' 98.5(11) . . ? Cl1 C87 Cl2' 127.0(9) . . ? Cl2 C87 Cl2' 55.3(6) . . ? N6 Cu1 N2 108.73(17) . . ? N6 Cu1 P4 96.21(14) . . ? N2 Cu1 P4 109.04(13) . . ? N6 Cu1 P1 112.67(14) . . ? N2 Cu1 P1 113.97(13) . . ? P4 Cu1 P1 114.74(6) . . ? N3 Cu2 N5 109.17(17) . . ? N3 Cu2 P2 96.25(12) . . ? N5 Cu2 P2 111.14(12) . . ? N3 Cu2 P3 110.92(13) . . ? N5 Cu2 P3 111.25(13) . . ? P2 Cu2 P3 117.03(6) . . ? C19 N1 C20 120.1(5) . . ? C24 N2 C20 116.6(5) . . ? C24 N2 Cu1 131.7(3) . . ? C20 N2 Cu1 108.6(3) . . ? C25 N3 C24 115.9(5) . . ? C25 N3 Cu2 126.8(4) . . ? C24 N3 Cu2 114.7(3) . . ? C62 N4 C63 121.4(5) . . ? C63 N5 C67 117.8(5) . . ? C63 N5 Cu2 109.1(3) . . ? C67 N5 Cu2 128.9(4) . . ? C68 N6 C67 116.1(5) . . ? C68 N6 Cu1 128.6(4) . . ? C67 N6 Cu1 114.0(3) . . ? C1 P1 C7 101.0(3) . . ? C1 P1 C13 101.7(3) . . ? C7 P1 C13 103.3(3) . . ? C1 P1 Cu1 121.8(2) . . ? C7 P1 Cu1 112.00(19) . . ? C13 P1 Cu1 114.7(2) . . ? C31 P2 C38 106.4(3) . . ? C31 P2 C32 100.5(3) . . ? C38 P2 C32 102.1(3) . . ? C31 P2 Cu2 108.76(18) . . ? C38 P2 Cu2 120.0(2) . . ? C32 P2 Cu2 116.95(18) . . ? C50 P3 C44 100.7(3) . . ? C50 P3 C56 104.0(3) . . ? C44 P3 C56 103.0(3) . . ? C50 P3 Cu2 119.0(2) . . ? C44 P3 Cu2 113.20(19) . . ? C56 P3 Cu2 114.89(18) . . ? C81 P4 C75 104.1(3) . . ? C81 P4 C74 99.9(3) . . ? C75 P4 C74 103.9(3) . . ? C81 P4 Cu1 117.9(2) . . ? C75 P4 Cu1 119.7(2) . . ? C74 P4 Cu1 108.7(2) . . ? F2 B1 F3 109.1(10) . . ? F2 B1 F4 108.3(12) . . ? F3 B1 F4 107.5(9) . . ? F2 B1 F1 102.4(9) . . ? F3 B1 F1 118.8(13) . . ? F4 B1 F1 110.4(10) . . ? F8 B2 F5 101.8(10) . . ? F8 B2 F6 93.2(10) . . ? F5 B2 F6 120.7(13) . . ? F8 B2 F7 122.9(12) . . ? F5 B2 F7 118.6(10) . . ? F6 B2 F7 98.2(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.103 _refine_diff_density_min -1.020 _refine_diff_density_rms 0.119 # Attachment 'compound_3.cif' data_a8901 _database_code_depnum_ccdc_archive 'CCDC 759229' #TrackingRef 'compound_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H33 Cu N4 O2 P2' _chemical_formula_sum 'C43 H33 Cu N4 O2 P2' _chemical_formula_weight 763.21 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.882(2) _cell_length_b 13.036(3) _cell_length_c 15.533(3) _cell_angle_alpha 81.005(5) _cell_angle_beta 76.103(7) _cell_angle_gamma 83.054(5) _cell_volume 1911.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3807 _cell_measurement_theta_min 2.226 _cell_measurement_theta_max 25.01 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7976 _exptl_absorpt_correction_T_max 0.9211 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6361 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6361 _reflns_number_gt 4244 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0782P)^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 6361 _refine_ls_number_parameters 463 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8037(4) 0.9527(3) 0.7796(3) 0.0331(10) Uani 1 1 d . . . C2 C 0.9086(5) 0.8723(4) 0.7631(3) 0.0463(12) Uani 1 1 d . . . H2 H 0.8926 0.8157 0.7360 0.056 Uiso 1 1 calc R . . C3 C 1.0362(5) 0.8731(4) 0.7853(3) 0.0557(14) Uani 1 1 d . . . H3 H 1.1068 0.8175 0.7738 0.067 Uiso 1 1 calc R . . C4 C 1.0596(5) 0.9551(4) 0.8242(3) 0.0552(14) Uani 1 1 d . . . H4 H 1.1470 0.9562 0.8394 0.066 Uiso 1 1 calc R . . C5 C 0.9579(5) 1.0352(4) 0.8412(3) 0.0522(13) Uani 1 1 d . . . H5 H 0.9750 1.0913 0.8684 0.063 Uiso 1 1 calc R . . C6 C 0.8291(5) 1.0350(3) 0.8190(3) 0.0421(11) Uani 1 1 d . . . H6 H 0.7592 1.0910 0.8307 0.050 Uiso 1 1 calc R . . C7 C 0.6744(4) 1.0330(3) 0.6349(3) 0.0312(10) Uani 1 1 d . . . C8 C 0.8046(4) 1.0674(3) 0.5931(3) 0.0409(11) Uani 1 1 d . . . H8 H 0.8793 1.0527 0.6231 0.049 Uiso 1 1 calc R . . C9 C 0.8265(5) 1.1234(4) 0.5075(3) 0.0460(12) Uani 1 1 d . . . H9 H 0.9161 1.1463 0.4793 0.055 Uiso 1 1 calc R . . C10 C 0.7190(5) 1.1454(4) 0.4643(3) 0.0496(13) Uani 1 1 d . . . H10 H 0.7345 1.1831 0.4058 0.059 Uiso 1 1 calc R . . C11 C 0.5880(5) 1.1132(4) 0.5054(3) 0.0471(12) Uani 1 1 d . . . H11 H 0.5131 1.1301 0.4757 0.057 Uiso 1 1 calc R . . C12 C 0.5665(5) 1.0569(3) 0.5889(3) 0.0404(11) Uani 1 1 d . . . H12 H 0.4768 1.0335 0.6161 0.048 Uiso 1 1 calc R . . C13 C 0.5050(4) 1.0200(3) 0.8159(3) 0.0331(10) Uani 1 1 d . . . C14 C 0.4566(5) 1.1212(4) 0.7902(3) 0.0423(11) Uani 1 1 d . . . H14 H 0.5020 1.1565 0.7344 0.051 Uiso 1 1 calc R . . C15 C 0.3440(5) 1.1732(4) 0.8430(3) 0.0496(13) Uani 1 1 d . . . H15 H 0.3129 1.2429 0.8237 0.060 Uiso 1 1 calc R . . C16 C 0.2781(5) 1.1221(4) 0.9237(3) 0.0500(13) Uani 1 1 d . . . H16 H 0.2004 1.1565 0.9605 0.060 Uiso 1 1 calc R . . C17 C 0.3241(4) 1.0223(4) 0.9510(3) 0.0404(11) Uani 1 1 d . . . H17 H 0.2780 0.9880 1.0070 0.048 Uiso 1 1 calc R . . C18 C 0.4376(4) 0.9694(3) 0.8985(3) 0.0339(10) Uani 1 1 d . . . C19 C 0.4904(4) 0.8646(3) 0.9321(3) 0.0363(10) Uani 1 1 d . . . H19 H 0.5758 0.8354 0.8984 0.044 Uiso 1 1 calc R . . C20 C 0.4988(4) 0.7103(3) 1.0235(3) 0.0361(10) Uani 1 1 d . . . C21 C 0.4444(5) 0.6476(4) 1.1022(3) 0.0445(12) Uani 1 1 d . . . H21 H 0.3611 0.6704 1.1420 0.053 Uiso 1 1 calc R . . C22 C 0.5141(5) 0.5513(4) 1.1212(3) 0.0451(12) Uani 1 1 d . . . H22 H 0.4791 0.5068 1.1745 0.054 Uiso 1 1 calc R . . C23 C 0.6340(5) 0.5206(4) 1.0626(3) 0.0436(11) Uani 1 1 d . . . H23 H 0.6846 0.4554 1.0750 0.052 Uiso 1 1 calc R . . C24 C 0.6799(4) 0.5875(4) 0.9845(3) 0.0370(10) Uani 1 1 d . . . C25 C 0.8064(4) 0.5956(3) 0.8397(3) 0.0326(10) Uani 1 1 d . . . H25 H 0.7215 0.6274 0.8254 0.039 Uiso 1 1 calc R . . C26 C 0.9318(4) 0.5907(3) 0.7676(3) 0.0303(9) Uani 1 1 d . . . C27 C 1.0611(4) 0.5577(3) 0.7874(3) 0.0363(10) Uani 1 1 d . . . H27 H 1.0654 0.5319 0.8475 0.044 Uiso 1 1 calc R . . C28 C 1.1832(4) 0.5615(3) 0.7223(3) 0.0393(11) Uani 1 1 d . . . H28 H 1.2708 0.5402 0.7376 0.047 Uiso 1 1 calc R . . C29 C 1.1771(4) 0.5966(3) 0.6349(3) 0.0378(11) Uani 1 1 d . . . H29 H 1.2609 0.5994 0.5896 0.045 Uiso 1 1 calc R . . C30 C 1.0489(4) 0.6280(3) 0.6126(3) 0.0323(10) Uani 1 1 d . . . H30 H 1.0458 0.6514 0.5519 0.039 Uiso 1 1 calc R . . C31 C 0.9256(4) 0.6253(3) 0.6780(3) 0.0287(9) Uani 1 1 d . . . C32 C 0.6944(4) 0.5389(3) 0.6455(2) 0.0281(9) Uani 1 1 d . . . C33 C 0.5660(4) 0.5391(3) 0.6232(3) 0.0353(10) Uani 1 1 d . . . H33 H 0.5094 0.6026 0.6154 0.042 Uiso 1 1 calc R . . C34 C 0.5213(5) 0.4463(4) 0.6123(3) 0.0405(11) Uani 1 1 d . . . H34 H 0.4339 0.4466 0.5968 0.049 Uiso 1 1 calc R . . C35 C 0.6021(5) 0.3534(4) 0.6236(3) 0.0451(12) Uani 1 1 d . . . H35 H 0.5716 0.2903 0.6147 0.054 Uiso 1 1 calc R . . C36 C 0.7270(5) 0.3528(4) 0.6479(3) 0.0471(12) Uani 1 1 d . . . H36 H 0.7820 0.2888 0.6573 0.057 Uiso 1 1 calc R . . C37 C 0.7729(4) 0.4449(3) 0.6588(3) 0.0373(10) Uani 1 1 d . . . H37 H 0.8595 0.4437 0.6755 0.045 Uiso 1 1 calc R . . C38 C 0.8018(4) 0.7127(3) 0.5272(3) 0.0287(9) Uani 1 1 d . . . C39 C 0.8304(4) 0.6461(3) 0.4620(3) 0.0373(10) Uani 1 1 d . . . H39 H 0.8320 0.5728 0.4790 0.045 Uiso 1 1 calc R . . C40 C 0.8565(5) 0.6869(4) 0.3724(3) 0.0455(12) Uani 1 1 d . . . H40 H 0.8751 0.6412 0.3281 0.055 Uiso 1 1 calc R . . C41 C 0.8558(5) 0.7927(4) 0.3466(3) 0.0443(12) Uani 1 1 d . . . H41 H 0.8737 0.8197 0.2849 0.053 Uiso 1 1 calc R . . C42 C 0.8290(4) 0.8598(4) 0.4109(3) 0.0415(11) Uani 1 1 d . . . H42 H 0.8297 0.9330 0.3935 0.050 Uiso 1 1 calc R . . C43 C 0.8011(4) 0.8192(3) 0.5007(3) 0.0355(10) Uani 1 1 d . . . H43 H 0.7813 0.8652 0.5448 0.043 Uiso 1 1 calc R . . Cu1 Cu 0.60839(5) 0.78615(4) 0.71977(3) 0.03016(17) Uani 1 1 d . . . N1 N 0.3725(4) 0.7386(3) 0.7723(2) 0.0284(6) Uani 1 1 d . . . N2 N 0.4302(4) 0.8097(3) 1.0031(2) 0.0400(9) Uani 1 1 d . . . N3 N 0.6154(3) 0.6800(3) 0.96592(19) 0.0284(6) Uani 1 1 d . . . N4 N 0.8054(3) 0.5589(3) 0.9212(2) 0.0385(9) Uani 1 1 d . . . O1 O 0.4351(6) 0.7106(4) 0.8150(4) 0.1053(17) Uani 1 1 d . . . O2 O 0.3960(5) 0.7862(5) 0.7120(4) 0.1158(18) Uani 1 1 d . . . P1 P 0.64556(11) 0.94728(9) 0.74101(7) 0.0315(3) Uani 1 1 d . . . P2 P 0.75649(10) 0.66552(8) 0.64673(7) 0.0267(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.039(2) 0.030(3) 0.028(2) -0.0050(19) -0.0035(18) -0.0061(19) C2 0.050(3) 0.045(3) 0.050(3) -0.016(2) -0.016(2) -0.005(2) C3 0.043(3) 0.055(4) 0.073(4) -0.015(3) -0.019(3) 0.000(2) C4 0.043(3) 0.076(4) 0.050(3) -0.006(3) -0.012(2) -0.018(3) C5 0.060(3) 0.062(4) 0.043(3) -0.015(3) -0.011(2) -0.028(3) C6 0.055(3) 0.034(3) 0.038(3) -0.008(2) -0.008(2) -0.008(2) C7 0.040(2) 0.025(2) 0.030(2) -0.0117(18) -0.0059(19) -0.0038(18) C8 0.042(3) 0.036(3) 0.048(3) -0.010(2) -0.009(2) -0.011(2) C9 0.056(3) 0.042(3) 0.038(3) 0.001(2) -0.004(2) -0.019(2) C10 0.080(4) 0.034(3) 0.038(3) -0.004(2) -0.012(3) -0.017(3) C11 0.067(3) 0.041(3) 0.039(3) -0.008(2) -0.018(2) -0.010(2) C12 0.047(3) 0.032(3) 0.044(3) -0.010(2) -0.010(2) -0.005(2) C13 0.035(2) 0.033(3) 0.033(2) -0.010(2) -0.0072(18) -0.0026(19) C14 0.052(3) 0.036(3) 0.040(3) -0.012(2) -0.007(2) -0.003(2) C15 0.056(3) 0.039(3) 0.057(3) -0.020(3) -0.017(3) 0.009(2) C16 0.047(3) 0.058(4) 0.050(3) -0.026(3) -0.014(2) 0.011(2) C17 0.038(3) 0.050(3) 0.033(2) -0.013(2) -0.0036(19) -0.002(2) C18 0.033(2) 0.038(3) 0.035(2) -0.017(2) -0.0087(19) -0.0043(19) C19 0.042(3) 0.038(3) 0.030(2) -0.014(2) -0.0039(19) -0.001(2) C20 0.039(2) 0.043(3) 0.027(2) -0.007(2) -0.0049(19) -0.007(2) C21 0.049(3) 0.051(3) 0.028(2) -0.008(2) 0.003(2) -0.008(2) C22 0.054(3) 0.052(3) 0.026(2) 0.002(2) -0.005(2) -0.011(2) C23 0.055(3) 0.043(3) 0.032(2) 0.001(2) -0.011(2) -0.001(2) C24 0.043(3) 0.047(3) 0.022(2) -0.006(2) -0.0078(19) -0.006(2) C25 0.036(2) 0.037(3) 0.025(2) -0.0027(19) -0.0095(18) -0.0008(19) C26 0.034(2) 0.029(2) 0.030(2) -0.0087(19) -0.0082(18) -0.0013(18) C27 0.041(3) 0.036(3) 0.034(2) -0.009(2) -0.010(2) -0.002(2) C28 0.032(2) 0.042(3) 0.048(3) -0.011(2) -0.015(2) -0.0015(19) C29 0.026(2) 0.040(3) 0.044(3) -0.011(2) 0.0012(19) -0.0024(19) C30 0.034(2) 0.033(3) 0.030(2) -0.0091(19) -0.0017(18) -0.0049(18) C31 0.033(2) 0.025(2) 0.031(2) -0.0106(18) -0.0084(18) -0.0036(17) C32 0.032(2) 0.032(3) 0.021(2) -0.0063(18) -0.0042(16) -0.0056(18) C33 0.035(2) 0.033(3) 0.039(2) -0.009(2) -0.0057(19) -0.0034(19) C34 0.045(3) 0.044(3) 0.036(3) -0.011(2) -0.006(2) -0.014(2) C35 0.065(3) 0.035(3) 0.039(3) -0.010(2) -0.006(2) -0.020(2) C36 0.067(3) 0.022(3) 0.051(3) -0.002(2) -0.013(2) -0.003(2) C37 0.038(2) 0.029(3) 0.045(3) -0.005(2) -0.009(2) 0.0001(19) C38 0.028(2) 0.030(3) 0.027(2) -0.0039(18) -0.0061(17) -0.0024(17) C39 0.055(3) 0.027(3) 0.028(2) -0.0031(19) -0.005(2) -0.006(2) C40 0.062(3) 0.047(3) 0.029(2) -0.014(2) -0.004(2) -0.013(2) C41 0.052(3) 0.055(3) 0.025(2) 0.000(2) -0.006(2) -0.013(2) C42 0.052(3) 0.031(3) 0.038(3) 0.001(2) -0.007(2) -0.004(2) C43 0.042(3) 0.032(3) 0.032(2) -0.007(2) -0.0062(19) -0.0041(19) Cu1 0.0327(3) 0.0291(3) 0.0287(3) -0.0079(2) -0.0039(2) -0.0037(2) N1 0.0392(15) 0.0331(17) 0.0141(12) 0.0039(11) -0.0136(11) -0.0020(12) N2 0.047(2) 0.040(2) 0.030(2) -0.0066(18) -0.0004(17) -0.0033(18) N3 0.0392(15) 0.0331(17) 0.0141(12) 0.0039(11) -0.0136(11) -0.0020(12) N4 0.040(2) 0.042(2) 0.033(2) -0.0063(17) -0.0058(16) -0.0014(16) O1 0.116(4) 0.078(4) 0.104(4) -0.036(3) 0.041(3) -0.041(3) O2 0.075(3) 0.140(5) 0.154(5) -0.056(4) -0.054(4) 0.008(3) P1 0.0355(6) 0.0280(6) 0.0307(6) -0.0082(5) -0.0023(5) -0.0061(5) P2 0.0295(6) 0.0273(6) 0.0238(5) -0.0076(5) -0.0033(4) -0.0047(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 C1 C2 1.390(6) . ? C1 C6 1.390(6) . ? C1 P1 1.816(4) . ? C2 C3 1.386(6) . ? C2 H2 0.9500 . ? C3 C4 1.374(7) . ? C3 H3 0.9500 . ? C4 C5 1.370(7) . ? C4 H4 0.9500 . ? C5 C6 1.396(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.387(6) . ? C7 C12 1.400(6) . ? C7 P1 1.823(4) . ? C8 C9 1.395(6) . ? C8 H8 0.9500 . ? C9 C10 1.368(6) . ? C9 H9 0.9500 . ? C10 C11 1.382(7) . ? C10 H10 0.9500 . ? C11 C12 1.369(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.379(6) . ? C13 C18 1.399(6) . ? C13 P1 1.852(4) . ? C14 C15 1.388(6) . ? C14 H14 0.9500 . ? C15 C16 1.375(7) . ? C15 H15 0.9500 . ? C16 C17 1.363(6) . ? C16 H16 0.9500 . ? C17 C18 1.396(5) . ? C17 H17 0.9500 . ? C18 C19 1.465(6) . ? C19 N2 1.275(5) . ? C19 H19 0.9500 . ? C20 N3 1.338(5) . ? C20 C21 1.389(6) . ? C20 N2 1.415(5) . ? C21 C22 1.383(6) . ? C21 H21 0.9500 . ? C22 C23 1.368(6) . ? C22 H22 0.9500 . ? C23 C24 1.393(6) . ? C23 H23 0.9500 . ? C24 N3 1.318(5) . ? C24 N4 1.436(5) . ? C25 N4 1.279(5) . ? C25 C26 1.459(5) . ? C25 H25 0.9500 . ? C26 C27 1.389(5) . ? C26 C31 1.408(5) . ? C27 C28 1.376(6) . ? C27 H27 0.9500 . ? C28 C29 1.376(6) . ? C28 H28 0.9500 . ? C29 C30 1.391(6) . ? C29 H29 0.9500 . ? C30 C31 1.386(5) . ? C30 H30 0.9500 . ? C31 P2 1.845(4) . ? C32 C37 1.383(6) . ? C32 C33 1.393(5) . ? C32 P2 1.833(4) . ? C33 C34 1.384(6) . ? C33 H33 0.9500 . ? C34 C35 1.379(6) . ? C34 H34 0.9500 . ? C35 C36 1.373(6) . ? C35 H35 0.9500 . ? C36 C37 1.382(6) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C39 1.392(5) . ? C38 C43 1.385(6) . ? C38 P2 1.827(4) . ? C39 C40 1.384(6) . ? C39 H39 0.9500 . ? C40 C41 1.374(6) . ? C40 H40 0.9500 . ? C41 C42 1.386(6) . ? C41 H41 0.9500 . ? C42 C43 1.387(6) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? Cu1 O2 2.131(4) . ? Cu1 O1 2.197(4) . ? Cu1 P2 2.2595(11) . ? Cu1 P1 2.2623(13) . ? Cu1 N1 2.400(4) . ? N1 O1 1.011(6) . ? N1 O2 1.032(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.6(4) . . ? C2 C1 P1 117.2(3) . . ? C6 C1 P1 124.0(3) . . ? C1 C2 C3 121.3(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.4(5) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.4(5) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 119.8(4) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C8 C7 C12 118.1(4) . . ? C8 C7 P1 122.1(3) . . ? C12 C7 P1 119.5(3) . . ? C7 C8 C9 120.5(4) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.3(5) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.9(5) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C7 121.2(4) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C14 C13 C18 118.1(4) . . ? C14 C13 P1 122.0(3) . . ? C18 C13 P1 119.7(3) . . ? C13 C14 C15 122.2(4) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C16 C15 C14 118.9(5) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 120.1(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 121.5(4) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C13 119.1(4) . . ? C17 C18 C19 120.2(4) . . ? C13 C18 C19 120.5(4) . . ? N2 C19 C18 124.8(4) . . ? N2 C19 H19 117.6 . . ? C18 C19 H19 117.6 . . ? N3 C20 C21 122.1(4) . . ? N3 C20 N2 118.4(4) . . ? C21 C20 N2 119.5(4) . . ? C22 C21 C20 118.5(4) . . ? C22 C21 H21 120.8 . . ? C20 C21 H21 120.8 . . ? C23 C22 C21 119.5(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 118.3(4) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? N3 C24 C23 122.9(4) . . ? N3 C24 N4 116.7(4) . . ? C23 C24 N4 120.3(4) . . ? N4 C25 C26 123.2(4) . . ? N4 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C27 C26 C31 118.9(4) . . ? C27 C26 C25 119.9(4) . . ? C31 C26 C25 121.1(4) . . ? C28 C27 C26 121.7(4) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C29 C28 C27 119.3(4) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 120.4(4) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C31 C30 C29 120.5(4) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C30 C31 C26 119.1(4) . . ? C30 C31 P2 119.9(3) . . ? C26 C31 P2 121.0(3) . . ? C37 C32 C33 118.9(4) . . ? C37 C32 P2 123.4(3) . . ? C33 C32 P2 117.6(3) . . ? C34 C33 C32 119.7(4) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C35 120.8(4) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C36 C35 C34 119.5(4) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? C35 C36 C37 120.2(4) . . ? C35 C36 H36 119.9 . . ? C37 C36 H36 119.9 . . ? C36 C37 C32 120.9(4) . . ? C36 C37 H37 119.6 . . ? C32 C37 H37 119.6 . . ? C39 C38 C43 119.0(4) . . ? C39 C38 P2 122.5(3) . . ? C43 C38 P2 118.5(3) . . ? C40 C39 C38 119.9(4) . . ? C40 C39 H39 120.1 . . ? C38 C39 H39 120.1 . . ? C41 C40 C39 120.8(4) . . ? C41 C40 H40 119.6 . . ? C39 C40 H40 119.6 . . ? C40 C41 C42 119.9(4) . . ? C40 C41 H41 120.0 . . ? C42 C41 H41 120.0 . . ? C41 C42 C43 119.4(4) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C38 C43 C42 121.0(4) . . ? C38 C43 H43 119.5 . . ? C42 C43 H43 119.5 . . ? O2 Cu1 O1 50.3(2) . . ? O2 Cu1 P2 114.24(14) . . ? O1 Cu1 P2 109.86(13) . . ? O2 Cu1 P1 108.88(16) . . ? O1 Cu1 P1 117.04(12) . . ? P2 Cu1 P1 129.86(4) . . ? O2 Cu1 N1 25.44(17) . . ? O1 Cu1 N1 24.91(16) . . ? P2 Cu1 N1 113.91(11) . . ? P1 Cu1 N1 116.05(11) . . ? O1 N1 O2 128.7(6) . . ? O1 N1 Cu1 66.2(4) . . ? O2 N1 Cu1 62.6(3) . . ? C19 N2 C20 115.7(4) . . ? C24 N3 C20 118.7(3) . . ? C25 N4 C24 114.9(4) . . ? N1 O1 Cu1 88.9(4) . . ? N1 O2 Cu1 92.0(4) . . ? C1 P1 C7 102.96(19) . . ? C1 P1 C13 105.56(18) . . ? C7 P1 C13 104.04(19) . . ? C1 P1 Cu1 114.40(14) . . ? C7 P1 Cu1 110.20(13) . . ? C13 P1 Cu1 118.15(14) . . ? C38 P2 C32 101.06(17) . . ? C38 P2 C31 105.04(18) . . ? C32 P2 C31 101.39(18) . . ? C38 P2 Cu1 109.67(13) . . ? C32 P2 Cu1 118.87(13) . . ? C31 P2 Cu1 118.65(12) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.606 _refine_diff_density_min -0.685 _refine_diff_density_rms 0.077