# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Fraysse, Sandrine' 'Stoeckli-Evans, Helen' 'von Zelewsky, A.' _publ_contact_author_name 'Prof A von Zelewsky' _publ_contact_author_address ; A stable chiral di-olefin complex of CuI with predetermined configuration at the metal centre ; _publ_contact_author_email 'ALEXANDER.VONZELEWSKY@UNIFR.CH' _publ_section_title ; A stable chiral di-olefin complex of CuI with predetermined configuration at the metal centre ; data_sf61 _database_code_CSD 170401 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H54 Cu F6 N2 O3 P' _chemical_formula_weight 771.32 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' 'F' 'F' 0.0171 0.0103 '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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.8728(11) _cell_length_b 15.8948(12) _cell_length_c 18.2031(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3724.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4811 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.02 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 0.696 _exptl_absorpt_correction_type empirical_DIFABS _exptl_absorpt_correction_T_min 0.412 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29366 _diffrn_reflns_av_R_equivalents 0.1784 _diffrn_reflns_av_sigmaI/netI 0.2841 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.02 _reflns_number_total 7281 _reflns_number_gt 2415 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS Software, 2000)' _computing_cell_refinement 'CELL (Stoe IPDS Software, 2000)' _computing_data_reduction 'INTEGRATE (Stoe IPDS Software, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00047(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 7281 _refine_ls_number_parameters 450 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1819 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1123 _refine_ls_wR_factor_gt 0.0816 _refine_ls_goodness_of_fit_ref 0.650 _refine_ls_restrained_S_all 0.650 _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 0.33489(8) 0.06076(6) 0.56681(5) 0.0475(3) Uani 1 1 d . . . N1 N 0.2504(5) -0.0121(4) 0.4981(3) 0.0368(16) Uani 1 1 d . . . N2 N 0.3174(5) 0.1454(4) 0.4854(4) 0.0402(17) Uani 1 1 d . . . C1 C 0.2218(6) 0.0290(4) 0.4353(4) 0.0400(18) Uani 1 1 d . . . C2 C 0.1609(8) -0.0109(5) 0.3841(4) 0.049(2) Uani 1 1 d . . . H2A H 0.1416 0.0167 0.3398 0.059 Uiso 1 1 calc R . . C3 C 0.1277(6) -0.0933(5) 0.3987(4) 0.045(2) Uani 1 1 d . . . H3A H 0.0888 -0.1229 0.3626 0.054 Uiso 1 1 calc R . . C4 C 0.1505(7) -0.1322(5) 0.4646(4) 0.0400(19) Uani 1 1 d . . . C5 C 0.1167(6) -0.2180(5) 0.4876(5) 0.048(2) Uani 1 1 d . . . H5A H 0.0708 -0.2491 0.4526 0.058 Uiso 1 1 calc R . . C6 C 0.2096(6) -0.2681(5) 0.5197(5) 0.047(2) Uani 1 1 d . . . C7 C 0.1891(6) -0.2150(5) 0.5917(4) 0.045(2) Uani 1 1 d . . . H7A H 0.2005 -0.2454 0.6391 0.054 Uiso 1 1 calc R . . C8 C 0.2423(6) -0.1294(5) 0.5851(4) 0.042(2) Uani 1 1 d . . . H8A H 0.3193 -0.1379 0.5867 0.050 Uiso 1 1 calc R . . C9 C 0.2142(6) -0.0898(5) 0.5128(4) 0.041(2) Uani 1 1 d . . . C10 C 0.0749(6) -0.2072(5) 0.5668(5) 0.054(2) Uani 1 1 d . . . H10B H 0.0432 -0.1516 0.5767 0.065 Uiso 1 1 calc R . . H10A H 0.0295 -0.2536 0.5837 0.065 Uiso 1 1 calc R . . C11 C 0.3114(7) -0.2650(6) 0.4841(5) 0.058(3) Uani 1 1 d . . . H11C H 0.3642 -0.2876 0.5175 0.087 Uiso 1 1 calc R . . H11B H 0.3285 -0.2066 0.4719 0.087 Uiso 1 1 calc R . . H11A H 0.3098 -0.2988 0.4391 0.087 Uiso 1 1 calc R . . C12 C 0.1796(7) -0.3626(5) 0.5324(5) 0.058(2) Uani 1 1 d . . . H12C H 0.2300 -0.3887 0.5656 0.087 Uiso 1 1 calc R . . H12B H 0.1798 -0.3924 0.4852 0.087 Uiso 1 1 calc R . . H12A H 0.1101 -0.3657 0.5542 0.087 Uiso 1 1 calc R . . C13 C 0.2103(6) -0.0681(6) 0.6492(4) 0.053(2) Uani 1 1 d . . . H13B H 0.1420 -0.0434 0.6364 0.064 Uiso 1 1 calc R . . H13A H 0.2001 -0.1024 0.6940 0.064 Uiso 1 1 calc R . . C14 C 0.2820(7) 0.0027(6) 0.6682(4) 0.052(2) Uani 1 1 d . . . H14A H 0.3524 -0.0112 0.6779 0.062 Uiso 1 1 calc R . . C15 C 0.2550(8) 0.0852(6) 0.6729(4) 0.061(3) Uani 1 1 d . . . H15A H 0.1854 0.1019 0.6636 0.073 Uiso 1 1 calc R . . H15B H 0.3058 0.1261 0.6854 0.073 Uiso 1 1 calc R . . C21 C 0.2622(5) 0.1153(4) 0.4276(5) 0.0412(19) Uani 1 1 d . . . C22 C 0.2477(7) 0.1631(5) 0.3642(4) 0.042(2) Uani 1 1 d . . . H22A H 0.2077 0.1423 0.3242 0.050 Uiso 1 1 calc R . . C23 C 0.2935(6) 0.2415(6) 0.3616(4) 0.051(2) Uani 1 1 d . . . H23A H 0.2831 0.2757 0.3194 0.061 Uiso 1 1 calc R . . C24 C 0.3545(6) 0.2724(4) 0.4190(4) 0.0383(19) Uani 1 1 d . . . C25 C 0.4087(6) 0.3562(5) 0.4245(5) 0.049(2) Uani 1 1 d . . . H25A H 0.4015 0.3941 0.3810 0.058 Uiso 1 1 calc R . . C26 C 0.3876(7) 0.3962(6) 0.4985(5) 0.050(2) Uani 1 1 d . . . C27 C 0.4720(6) 0.3366(5) 0.5283(4) 0.048(2) Uani 1 1 d . . . H27A H 0.5169 0.3608 0.5679 0.057 Uiso 1 1 calc R . . C28 C 0.4315(6) 0.2477(5) 0.5432(4) 0.042(2) Uani 1 1 d . . . H28A H 0.3897 0.2491 0.5895 0.050 Uiso 1 1 calc R . . C29 C 0.3618(6) 0.2199(5) 0.4819(4) 0.041(2) Uani 1 1 d . . . C30 C 0.5198(7) 0.3387(6) 0.4499(5) 0.060(3) Uani 1 1 d . . . H30B H 0.5690 0.3856 0.4414 0.072 Uiso 1 1 calc R . . H30A H 0.5486 0.2843 0.4330 0.072 Uiso 1 1 calc R . . C31 C 0.2797(6) 0.3932(5) 0.5325(4) 0.053(2) Uani 1 1 d . . . H31C H 0.2826 0.4152 0.5827 0.080 Uiso 1 1 calc R . . H31B H 0.2550 0.3349 0.5335 0.080 Uiso 1 1 calc R . . H31A H 0.2319 0.4275 0.5031 0.080 Uiso 1 1 calc R . . C32 C 0.4205(7) 0.4880(6) 0.5002(5) 0.066(3) Uani 1 1 d . . . H32C H 0.4104 0.5105 0.5499 0.099 Uiso 1 1 calc R . . H32B H 0.3782 0.5202 0.4654 0.099 Uiso 1 1 calc R . . H32A H 0.4939 0.4925 0.4866 0.099 Uiso 1 1 calc R . . C33 C 0.5215(6) 0.1842(5) 0.5538(5) 0.054(2) Uani 1 1 d . . . H33B H 0.5502 0.1711 0.5046 0.065 Uiso 1 1 calc R . . H33A H 0.5771 0.2130 0.5818 0.065 Uiso 1 1 calc R . . C34 C 0.4991(7) 0.1019(6) 0.5918(5) 0.056(3) Uani 1 1 d . . . H34A H 0.4792 0.1047 0.6420 0.067 Uiso 1 1 calc R . . C35 C 0.5047(6) 0.0247(6) 0.5613(6) 0.063(3) Uani 1 1 d . . . H35A H 0.5242 0.0187 0.5112 0.075 Uiso 1 1 calc R . . H35B H 0.4890 -0.0237 0.5898 0.075 Uiso 1 1 calc R . . P1 P 0.0461(3) 0.6740(2) 0.26794(16) 0.0803(10) Uani 1 1 d . . . F1 F -0.0277(5) 0.7003(6) 0.3332(3) 0.128(3) Uani 1 1 d . . . F2 F 0.1241(5) 0.6474(4) 0.2042(3) 0.091(2) Uani 1 1 d . . . F3 F -0.0299(6) 0.7128(7) 0.2084(4) 0.150(4) Uani 1 1 d . . . F4 F 0.1233(8) 0.6348(7) 0.3260(3) 0.175(4) Uani 1 1 d . . . F5 F -0.0110(7) 0.5884(6) 0.2587(5) 0.203(5) Uani 1 1 d . . . F6 F 0.1001(5) 0.7604(4) 0.2731(4) 0.117(3) Uani 1 1 d . . . C41 C 0.5274(12) 0.2374(13) 0.2642(9) 0.202(10) Uani 1 1 d . . . H41C H 0.5205 0.2955 0.2815 0.303 Uiso 1 1 calc R . . H41B H 0.5108 0.1986 0.3043 0.303 Uiso 1 1 calc R . . H41A H 0.4794 0.2280 0.2232 0.303 Uiso 1 1 calc R . . C42 C 0.6342(14) 0.2228(12) 0.2394(15) 0.254(15) Uani 1 1 d . . . H42A H 0.6504 0.2590 0.1966 0.305 Uiso 1 1 calc R . . H42B H 0.6839 0.2359 0.2793 0.305 Uiso 1 1 calc R . . O43 O 0.6414(17) 0.1360(11) 0.2194(8) 0.235(6) Uani 1 1 d . . . H43 H 0.6784 0.1312 0.1816 0.352 Uiso 1 1 calc R . . C51 C 0.1296(10) 0.4009(11) 0.2169(8) 0.159(8) Uani 1 1 d . . . H51C H 0.0701 0.4385 0.2101 0.238 Uiso 1 1 calc R . . H51B H 0.1110 0.3561 0.2514 0.238 Uiso 1 1 calc R . . H51A H 0.1490 0.3760 0.1695 0.238 Uiso 1 1 calc R . . C52 C 0.2197(10) 0.4498(10) 0.2469(11) 0.179(10) Uani 1 1 d . . . H52B H 0.2288 0.5041 0.2209 0.215 Uiso 1 1 calc R . . H52A H 0.2123 0.4603 0.3002 0.215 Uiso 1 1 calc R . . O53 O 0.3059(8) 0.3910(6) 0.2310(6) 0.147(4) Uani 1 1 d . . . H53 H 0.3594 0.4184 0.2201 0.221 Uiso 1 1 calc R . . C61 C 0.5619(10) 0.4259(12) 0.1628(9) 0.194(9) Uani 1 1 d . . . H61C H 0.5706 0.4113 0.1109 0.291 Uiso 1 1 calc R . . H61B H 0.5178 0.3838 0.1868 0.291 Uiso 1 1 calc R . . H61A H 0.6300 0.4272 0.1869 0.291 Uiso 1 1 calc R . . C62 C 0.5067(19) 0.5194(11) 0.1694(10) 0.255(14) Uani 1 1 d . . . H62B H 0.5558 0.5667 0.1628 0.305 Uiso 1 1 calc R . . H62A H 0.4452 0.5262 0.1373 0.305 Uiso 1 1 calc R . . O63 O 0.4795(12) 0.5026(8) 0.2487(8) 0.193(5) Uani 1 1 d . . . H63 H 0.4825 0.5477 0.2726 0.290 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0518(6) 0.0425(5) 0.0483(5) -0.0007(6) -0.0137(6) -0.0001(6) N1 0.041(4) 0.031(4) 0.039(4) 0.007(3) 0.000(3) 0.008(3) N2 0.032(4) 0.033(4) 0.056(4) -0.006(3) -0.008(3) -0.009(3) C1 0.048(5) 0.038(4) 0.034(4) 0.005(4) 0.001(4) 0.014(4) C2 0.055(6) 0.046(5) 0.046(5) -0.003(4) -0.003(5) -0.009(6) C3 0.040(5) 0.042(5) 0.055(5) -0.018(4) -0.010(4) 0.001(4) C4 0.038(5) 0.039(4) 0.043(4) -0.001(3) -0.010(4) -0.004(4) C5 0.034(5) 0.044(5) 0.067(6) -0.015(5) -0.010(4) -0.001(4) C6 0.043(5) 0.037(5) 0.062(5) -0.001(4) -0.004(4) 0.002(4) C7 0.045(6) 0.033(4) 0.056(5) 0.004(4) -0.008(4) 0.006(4) C8 0.037(5) 0.048(5) 0.040(5) 0.001(4) 0.003(4) 0.013(4) C9 0.034(5) 0.045(5) 0.043(5) -0.001(4) -0.007(4) 0.009(4) C10 0.039(5) 0.060(6) 0.063(5) -0.002(6) 0.011(5) -0.002(4) C11 0.054(7) 0.061(6) 0.060(6) 0.004(5) 0.003(5) -0.001(5) C12 0.053(6) 0.039(5) 0.082(6) 0.004(4) 0.000(5) -0.005(5) C13 0.063(6) 0.050(5) 0.046(4) -0.004(5) -0.013(4) -0.002(5) C14 0.053(6) 0.057(6) 0.045(5) 0.008(5) -0.010(4) -0.003(5) C15 0.069(7) 0.061(7) 0.051(5) -0.008(5) -0.006(5) 0.004(5) C21 0.040(5) 0.034(4) 0.050(5) -0.004(5) 0.003(4) 0.003(4) C22 0.054(6) 0.035(5) 0.037(4) 0.002(4) -0.004(4) -0.009(4) C23 0.046(6) 0.062(6) 0.044(5) 0.010(5) 0.004(4) 0.021(5) C24 0.040(5) 0.039(4) 0.037(5) 0.000(3) 0.000(4) 0.000(4) C25 0.054(5) 0.036(5) 0.055(5) 0.002(5) -0.013(5) -0.005(4) C26 0.056(6) 0.040(5) 0.055(5) -0.003(4) -0.002(5) -0.010(4) C27 0.048(5) 0.034(5) 0.062(5) -0.005(4) -0.001(4) -0.008(5) C28 0.042(5) 0.041(5) 0.042(5) -0.003(4) -0.006(4) 0.004(4) C29 0.036(5) 0.048(5) 0.038(4) 0.004(4) 0.000(4) -0.010(4) C30 0.056(6) 0.053(6) 0.072(7) -0.009(5) 0.007(5) -0.017(5) C31 0.057(6) 0.043(5) 0.059(5) -0.006(4) -0.013(5) -0.001(5) C32 0.055(6) 0.054(6) 0.090(7) 0.000(5) -0.017(6) -0.005(5) C33 0.055(5) 0.046(5) 0.062(6) 0.008(5) -0.008(5) 0.013(4) C34 0.038(5) 0.063(7) 0.067(6) 0.012(5) -0.009(4) -0.009(5) C35 0.037(5) 0.067(6) 0.084(7) -0.007(6) -0.020(5) 0.004(4) P1 0.088(2) 0.095(2) 0.0581(16) 0.0036(17) 0.0000(16) -0.039(2) F1 0.071(4) 0.228(9) 0.086(4) -0.035(5) 0.036(4) -0.034(5) F2 0.108(6) 0.110(5) 0.055(3) 0.000(3) 0.016(3) -0.009(4) F3 0.081(5) 0.278(12) 0.092(5) 0.001(6) -0.017(4) -0.003(7) F4 0.227(11) 0.246(10) 0.051(4) 0.057(5) 0.004(5) 0.040(8) F5 0.222(9) 0.248(12) 0.138(7) -0.023(7) 0.032(6) -0.194(9) F6 0.138(7) 0.084(5) 0.130(6) -0.032(4) 0.048(5) -0.045(5) C41 0.117(14) 0.33(3) 0.162(16) -0.103(18) 0.047(13) -0.016(17) C42 0.127(18) 0.186(19) 0.45(4) -0.23(2) -0.015(19) 0.033(15) O43 0.29(2) 0.244(15) 0.169(11) -0.016(11) 0.021(13) -0.050(17) C51 0.082(11) 0.26(2) 0.135(12) 0.025(13) 0.022(9) 0.006(12) C52 0.048(8) 0.117(14) 0.37(3) 0.124(17) 0.036(12) 0.044(10) O53 0.177(11) 0.139(8) 0.125(7) 0.047(6) -0.011(8) -0.067(8) C61 0.086(11) 0.24(2) 0.26(2) -0.162(18) -0.006(12) 0.006(14) C62 0.42(3) 0.132(17) 0.211(19) 0.009(14) 0.24(2) -0.016(19) O63 0.142(10) 0.201(14) 0.237(14) -0.007(10) 0.001(10) -0.067(11) _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 N2 2.015(6) . ? Cu1 N1 2.022(7) . ? Cu1 C14 2.174(8) . ? Cu1 C15 2.222(8) . ? Cu1 C34 2.259(8) . ? Cu1 C35 2.262(8) . ? N1 C9 1.348(9) . ? N1 C1 1.367(9) . ? N2 C29 1.315(9) . ? N2 C21 1.356(9) . ? C1 C2 1.373(11) . ? C1 C21 1.473(9) . ? C2 C3 1.404(10) . ? C2 H2A 0.9500 . ? C3 C4 1.380(10) . ? C3 H3A 0.9500 . ? C4 C9 1.377(10) . ? C4 C5 1.492(11) . ? C5 C10 1.548(11) . ? C5 C6 1.550(11) . ? C5 H5A 1.0000 . ? C6 C11 1.464(11) . ? C6 C12 1.567(11) . ? C6 C7 1.580(10) . ? C7 C8 1.528(11) . ? C7 C10 1.543(10) . ? C7 H7A 1.0000 . ? C8 C9 1.504(10) . ? C8 C13 1.576(10) . ? C8 H8A 1.0000 . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C11 H11C 0.9800 . ? C11 H11B 0.9800 . ? C11 H11A 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C13 C14 1.496(12) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.359(12) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C15 H15B 0.9500 . ? C21 C22 1.394(10) . ? C22 C23 1.380(11) . ? C22 H22A 0.9500 . ? C23 C24 1.397(10) . ? C23 H23A 0.9500 . ? C24 C29 1.421(10) . ? C24 C25 1.507(10) . ? C25 C26 1.513(12) . ? C25 C30 1.529(11) . ? C25 H25A 1.0000 . ? C26 C32 1.519(10) . ? C26 C31 1.522(11) . ? C26 C27 1.541(12) . ? C27 C28 1.530(11) . ? C27 C30 1.553(10) . ? C27 H27A 1.0000 . ? C28 C29 1.497(10) . ? C28 C33 1.549(10) . ? C28 H28A 1.0000 . ? C30 H30B 0.9900 . ? C30 H30A 0.9900 . ? C31 H31C 0.9800 . ? C31 H31B 0.9800 . ? C31 H31A 0.9800 . ? C32 H32C 0.9800 . ? C32 H32B 0.9800 . ? C32 H32A 0.9800 . ? C33 C34 1.509(11) . ? C33 H33B 0.9900 . ? C33 H33A 0.9900 . ? C34 C35 1.349(11) . ? C34 H34A 0.9500 . ? C35 H35A 0.9500 . ? C35 H35B 0.9500 . ? P1 F6 1.543(7) . ? P1 F5 1.555(8) . ? P1 F1 1.578(6) . ? P1 F4 1.579(8) . ? P1 F3 1.584(8) . ? P1 F2 1.591(6) . ? C41 C42 1.466(18) . ? C41 H41C 0.9800 . ? C41 H41B 0.9800 . ? C41 H41A 0.9800 . ? C42 O43 1.429(19) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? O43 H43 0.8400 . ? C51 C52 1.499(19) . ? C51 H51C 0.9800 . ? C51 H51B 0.9800 . ? C51 H51A 0.9800 . ? C52 O53 1.480(14) . ? C52 H52B 0.9900 . ? C52 H52A 0.9900 . ? O53 H53 0.8400 . ? C61 C62 1.65(2) . ? C61 H61C 0.9800 . ? C61 H61B 0.9800 . ? C61 H61A 0.9800 . ? C62 O63 1.509(17) . ? C62 H62B 0.9900 . ? C62 H62A 0.9900 . ? O63 H63 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 82.3(2) . . ? N2 Cu1 C14 150.9(3) . . ? N1 Cu1 C14 96.6(3) . . ? N2 Cu1 C15 118.1(3) . . ? N1 Cu1 C15 112.9(3) . . ? C14 Cu1 C15 36.0(3) . . ? N2 Cu1 C34 93.4(3) . . ? N1 Cu1 C34 142.5(3) . . ? C14 Cu1 C34 104.2(3) . . ? C15 Cu1 C34 102.0(4) . . ? N2 Cu1 C35 104.2(3) . . ? N1 Cu1 C35 110.3(3) . . ? C14 Cu1 C35 103.5(4) . . ? C15 Cu1 C35 122.0(4) . . ? C34 Cu1 C35 34.7(3) . . ? C9 N1 C1 120.7(7) . . ? C9 N1 Cu1 126.0(5) . . ? C1 N1 Cu1 112.9(5) . . ? C29 N2 C21 120.6(7) . . ? C29 N2 Cu1 125.9(5) . . ? C21 N2 Cu1 113.2(5) . . ? N1 C1 C2 120.0(7) . . ? N1 C1 C21 115.4(8) . . ? C2 C1 C21 124.6(8) . . ? C1 C2 C3 118.5(8) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C4 C3 C2 121.2(8) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C9 C4 C3 117.5(7) . . ? C9 C4 C5 116.2(7) . . ? C3 C4 C5 126.3(7) . . ? C4 C5 C10 105.2(6) . . ? C4 C5 C6 110.6(7) . . ? C10 C5 C6 88.6(6) . . ? C4 C5 H5A 116.3 . . ? C10 C5 H5A 116.3 . . ? C6 C5 H5A 116.3 . . ? C11 C6 C5 120.4(7) . . ? C11 C6 C12 108.5(7) . . ? C5 C6 C12 110.9(7) . . ? C11 C6 C7 119.9(7) . . ? C5 C6 C7 84.8(6) . . ? C12 C6 C7 110.4(7) . . ? C8 C7 C10 109.4(6) . . ? C8 C7 C6 109.6(6) . . ? C10 C7 C6 87.6(6) . . ? C8 C7 H7A 115.6 . . ? C10 C7 H7A 115.6 . . ? C6 C7 H7A 115.6 . . ? C9 C8 C7 109.4(6) . . ? C9 C8 C13 109.0(6) . . ? C7 C8 C13 112.1(6) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.8 . . ? C13 C8 H8A 108.7 . . ? N1 C9 C4 121.9(7) . . ? N1 C9 C8 118.3(7) . . ? C4 C9 C8 119.8(7) . . ? C7 C10 C5 86.1(6) . . ? C7 C10 H10B 114.3 . . ? C5 C10 H10B 114.3 . . ? C7 C10 H10A 114.3 . . ? C5 C10 H10A 114.3 . . ? H10B C10 H10A 111.4 . . ? C6 C11 H11C 109.5 . . ? C6 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C6 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? C6 C12 H12C 109.5 . . ? C6 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? C6 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? C14 C13 C8 118.4(7) . . ? C14 C13 H13B 107.7 . . ? C8 C13 H13B 107.7 . . ? C14 C13 H13A 107.7 . . ? C8 C13 H13A 107.7 . . ? H13B C13 H13A 107.1 . . ? C15 C14 C13 125.6(9) . . ? C15 C14 Cu1 73.9(6) . . ? C13 C14 Cu1 108.4(5) . . ? C15 C14 H14A 117.2 . . ? C13 C14 H14A 117.2 . . ? Cu1 C14 H14A 87.6 . . ? C14 C15 Cu1 70.1(5) . . ? C14 C15 H15A 120.0 . . ? Cu1 C15 H15A 109.4 . . ? C14 C15 H15B 120.0 . . ? Cu1 C15 H15B 90.5 . . ? H15A C15 H15B 120.0 . . ? N2 C21 C22 121.3(7) . . ? N2 C21 C1 116.1(8) . . ? C22 C21 C1 122.5(8) . . ? C23 C22 C21 117.6(7) . . ? C23 C22 H22A 121.2 . . ? C21 C22 H22A 121.2 . . ? C22 C23 C24 122.2(8) . . ? C22 C23 H23A 118.9 . . ? C24 C23 H23A 118.9 . . ? C23 C24 C29 115.7(7) . . ? C23 C24 C25 128.4(7) . . ? C29 C24 C25 115.8(7) . . ? C24 C25 C26 110.4(7) . . ? C24 C25 C30 107.0(7) . . ? C26 C25 C30 88.6(7) . . ? C24 C25 H25A 115.9 . . ? C26 C25 H25A 115.9 . . ? C30 C25 H25A 115.9 . . ? C25 C26 C32 111.9(8) . . ? C25 C26 C31 120.8(7) . . ? C32 C26 C31 106.0(8) . . ? C25 C26 C27 85.9(7) . . ? C32 C26 C27 112.7(7) . . ? C31 C26 C27 118.8(7) . . ? C28 C27 C26 112.9(7) . . ? C28 C27 C30 108.6(7) . . ? C26 C27 C30 86.7(6) . . ? C28 C27 H27A 115.1 . . ? C26 C27 H27A 115.1 . . ? C30 C27 H27A 115.1 . . ? C29 C28 C27 110.2(7) . . ? C29 C28 C33 110.4(6) . . ? C27 C28 C33 111.6(7) . . ? C29 C28 H28A 108.2 . . ? C27 C28 H28A 108.2 . . ? C33 C28 H28A 108.2 . . ? N2 C29 C24 122.5(7) . . ? N2 C29 C28 119.4(7) . . ? C24 C29 C28 117.8(7) . . ? C25 C30 C27 84.9(7) . . ? C25 C30 H30B 114.5 . . ? C27 C30 H30B 114.5 . . ? C25 C30 H30A 114.5 . . ? C27 C30 H30A 114.5 . . ? H30B C30 H30A 111.6 . . ? C26 C31 H31C 109.5 . . ? C26 C31 H31B 109.5 . . ? H31C C31 H31B 109.5 . . ? C26 C31 H31A 109.5 . . ? H31C C31 H31A 109.5 . . ? H31B C31 H31A 109.5 . . ? C26 C32 H32C 109.5 . . ? C26 C32 H32B 109.5 . . ? H32C C32 H32B 109.5 . . ? C26 C32 H32A 109.5 . . ? H32C C32 H32A 109.5 . . ? H32B C32 H32A 109.5 . . ? C34 C33 C28 118.6(7) . . ? C34 C33 H33B 107.7 . . ? C28 C33 H33B 107.7 . . ? C34 C33 H33A 107.7 . . ? C28 C33 H33A 107.7 . . ? H33B C33 H33A 107.1 . . ? C35 C34 C33 126.2(9) . . ? C35 C34 Cu1 72.8(5) . . ? C33 C34 Cu1 109.7(5) . . ? C35 C34 H34A 116.9 . . ? C33 C34 H34A 116.9 . . ? Cu1 C34 H34A 87.4 . . ? C34 C35 Cu1 72.5(6) . . ? C34 C35 H35A 120.0 . . ? Cu1 C35 H35A 108.9 . . ? C34 C35 H35B 120.0 . . ? Cu1 C35 H35B 88.6 . . ? H35A C35 H35B 120.0 . . ? F6 P1 F5 176.9(5) . . ? F6 P1 F1 89.4(4) . . ? F5 P1 F1 91.7(5) . . ? F6 P1 F4 91.5(5) . . ? F5 P1 F4 91.5(6) . . ? F1 P1 F4 88.8(4) . . ? F6 P1 F3 88.5(5) . . ? F5 P1 F3 88.5(5) . . ? F1 P1 F3 92.3(4) . . ? F4 P1 F3 178.9(5) . . ? F6 P1 F2 89.8(4) . . ? F5 P1 F2 89.3(4) . . ? F1 P1 F2 177.8(4) . . ? F4 P1 F2 89.2(4) . . ? F3 P1 F2 89.7(4) . . ? C42 C41 H41C 109.5 . . ? C42 C41 H41B 109.5 . . ? H41C C41 H41B 109.5 . . ? C42 C41 H41A 109.5 . . ? H41C C41 H41A 109.5 . . ? H41B C41 H41A 109.5 . . ? O43 C42 C41 107.0(18) . . ? O43 C42 H42A 110.3 . . ? C41 C42 H42A 110.3 . . ? O43 C42 H42B 110.3 . . ? C41 C42 H42B 110.3 . . ? H42A C42 H42B 108.6 . . ? C42 O43 H43 109.5 . . ? C52 C51 H51C 109.5 . . ? C52 C51 H51B 109.5 . . ? H51C C51 H51B 109.5 . . ? C52 C51 H51A 109.5 . . ? H51C C51 H51A 109.5 . . ? H51B C51 H51A 109.5 . . ? O53 C52 C51 100.4(13) . . ? O53 C52 H52B 111.7 . . ? C51 C52 H52B 111.7 . . ? O53 C52 H52A 111.7 . . ? C51 C52 H52A 111.7 . . ? H52B C52 H52A 109.5 . . ? C52 O53 H53 109.5 . . ? C62 C61 H61C 109.5 . . ? C62 C61 H61B 109.5 . . ? H61C C61 H61B 109.5 . . ? C62 C61 H61A 109.5 . . ? H61C C61 H61A 109.5 . . ? H61B C61 H61A 109.5 . . ? O63 C62 C61 90.6(14) . . ? O63 C62 H62B 113.5 . . ? C61 C62 H62B 113.5 . . ? O63 C62 H62A 113.5 . . ? C61 C62 H62A 113.5 . . ? H62B C62 H62A 110.8 . . ? C62 O63 H63 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C9 -174.7(6) . . . . ? C14 Cu1 N1 C9 -24.1(7) . . . . ? C15 Cu1 N1 C9 -57.4(7) . . . . ? C34 Cu1 N1 C9 99.7(7) . . . . ? C35 Cu1 N1 C9 82.9(7) . . . . ? N2 Cu1 N1 C1 -1.7(5) . . . . ? C14 Cu1 N1 C1 149.0(5) . . . . ? C15 Cu1 N1 C1 115.6(5) . . . . ? C34 Cu1 N1 C1 -87.3(6) . . . . ? C35 Cu1 N1 C1 -104.0(6) . . . . ? N1 Cu1 N2 C29 -173.6(7) . . . . ? C14 Cu1 N2 C29 96.7(9) . . . . ? C15 Cu1 N2 C29 74.5(7) . . . . ? C34 Cu1 N2 C29 -31.0(7) . . . . ? C35 Cu1 N2 C29 -64.5(7) . . . . ? N1 Cu1 N2 C21 -0.4(5) . . . . ? C14 Cu1 N2 C21 -90.1(8) . . . . ? C15 Cu1 N2 C21 -112.3(6) . . . . ? C34 Cu1 N2 C21 142.2(6) . . . . ? C35 Cu1 N2 C21 108.7(6) . . . . ? C9 N1 C1 C2 -4.2(11) . . . . ? Cu1 N1 C1 C2 -177.7(6) . . . . ? C9 N1 C1 C21 176.8(7) . . . . ? Cu1 N1 C1 C21 3.4(8) . . . . ? N1 C1 C2 C3 1.2(12) . . . . ? C21 C1 C2 C3 -179.9(7) . . . . ? C1 C2 C3 C4 3.6(13) . . . . ? C2 C3 C4 C9 -5.3(12) . . . . ? C2 C3 C4 C5 177.8(9) . . . . ? C9 C4 C5 C10 50.1(9) . . . . ? C3 C4 C5 C10 -132.9(8) . . . . ? C9 C4 C5 C6 -44.2(9) . . . . ? C3 C4 C5 C6 132.8(9) . . . . ? C4 C5 C6 C11 -42.6(10) . . . . ? C10 C5 C6 C11 -148.3(8) . . . . ? C4 C5 C6 C12 -170.9(7) . . . . ? C10 C5 C6 C12 83.4(7) . . . . ? C4 C5 C6 C7 79.2(7) . . . . ? C10 C5 C6 C7 -26.5(6) . . . . ? C11 C6 C7 C8 39.1(10) . . . . ? C5 C6 C7 C8 -83.2(7) . . . . ? C12 C6 C7 C8 166.3(7) . . . . ? C11 C6 C7 C10 148.9(8) . . . . ? C5 C6 C7 C10 26.6(6) . . . . ? C12 C6 C7 C10 -83.9(7) . . . . ? C10 C7 C8 C9 -44.8(8) . . . . ? C6 C7 C8 C9 49.8(8) . . . . ? C10 C7 C8 C13 76.3(8) . . . . ? C6 C7 C8 C13 170.8(6) . . . . ? C1 N1 C9 C4 2.4(11) . . . . ? Cu1 N1 C9 C4 174.9(6) . . . . ? C1 N1 C9 C8 -175.8(7) . . . . ? Cu1 N1 C9 C8 -3.2(10) . . . . ? C3 C4 C9 N1 2.3(11) . . . . ? C5 C4 C9 N1 179.6(7) . . . . ? C3 C4 C9 C8 -179.5(7) . . . . ? C5 C4 C9 C8 -2.2(11) . . . . ? C7 C8 C9 N1 177.3(7) . . . . ? C13 C8 C9 N1 54.4(9) . . . . ? C7 C8 C9 C4 -0.9(9) . . . . ? C13 C8 C9 C4 -123.8(8) . . . . ? C8 C7 C10 C5 83.5(7) . . . . ? C6 C7 C10 C5 -26.5(6) . . . . ? C4 C5 C10 C7 -83.8(7) . . . . ? C6 C5 C10 C7 27.1(6) . . . . ? C9 C8 C13 C14 -81.9(9) . . . . ? C7 C8 C13 C14 156.8(7) . . . . ? C8 C13 C14 C15 127.3(10) . . . . ? C8 C13 C14 Cu1 44.2(9) . . . . ? N2 Cu1 C14 C15 -34.5(10) . . . . ? N1 Cu1 C14 C15 -120.5(6) . . . . ? C34 Cu1 C14 C15 90.9(7) . . . . ? C35 Cu1 C14 C15 126.7(6) . . . . ? N2 Cu1 C14 C13 88.4(9) . . . . ? N1 Cu1 C14 C13 2.3(6) . . . . ? C15 Cu1 C14 C13 122.9(9) . . . . ? C34 Cu1 C14 C13 -146.2(6) . . . . ? C35 Cu1 C14 C13 -110.4(6) . . . . ? C13 C14 C15 Cu1 -101.4(8) . . . . ? N2 Cu1 C15 C14 161.8(5) . . . . ? N1 Cu1 C15 C14 68.3(7) . . . . ? C34 Cu1 C15 C14 -97.7(6) . . . . ? C35 Cu1 C15 C14 -66.8(7) . . . . ? C29 N2 C21 C22 -2.3(11) . . . . ? Cu1 N2 C21 C22 -175.9(6) . . . . ? C29 N2 C21 C1 175.9(7) . . . . ? Cu1 N2 C21 C1 2.3(8) . . . . ? N1 C1 C21 N2 -3.8(10) . . . . ? C2 C1 C21 N2 177.2(8) . . . . ? N1 C1 C21 C22 174.4(7) . . . . ? C2 C1 C21 C22 -4.5(12) . . . . ? N2 C21 C22 C23 1.4(12) . . . . ? C1 C21 C22 C23 -176.7(7) . . . . ? C21 C22 C23 C24 1.5(12) . . . . ? C22 C23 C24 C29 -3.3(12) . . . . ? C22 C23 C24 C25 -179.6(8) . . . . ? C23 C24 C25 C26 132.5(9) . . . . ? C29 C24 C25 C26 -43.8(9) . . . . ? C23 C24 C25 C30 -132.6(9) . . . . ? C29 C24 C25 C30 51.2(9) . . . . ? C24 C25 C26 C32 -167.5(7) . . . . ? C30 C25 C26 C32 84.8(8) . . . . ? C24 C25 C26 C31 -41.7(11) . . . . ? C30 C25 C26 C31 -149.3(8) . . . . ? C24 C25 C26 C27 79.6(7) . . . . ? C30 C25 C26 C27 -28.0(6) . . . . ? C25 C26 C27 C28 -81.2(7) . . . . ? C32 C26 C27 C28 166.8(8) . . . . ? C31 C26 C27 C28 42.0(10) . . . . ? C25 C26 C27 C30 27.6(6) . . . . ? C32 C26 C27 C30 -84.4(8) . . . . ? C31 C26 C27 C30 150.7(8) . . . . ? C26 C27 C28 C29 42.5(9) . . . . ? C30 C27 C28 C29 -51.9(9) . . . . ? C26 C27 C28 C33 165.5(7) . . . . ? C30 C27 C28 C33 71.2(8) . . . . ? C21 N2 C29 C24 0.3(12) . . . . ? Cu1 N2 C29 C24 173.1(6) . . . . ? C21 N2 C29 C28 -173.6(7) . . . . ? Cu1 N2 C29 C28 -0.8(11) . . . . ? C23 C24 C29 N2 2.4(12) . . . . ? C25 C24 C29 N2 179.1(7) . . . . ? C23 C24 C29 C28 176.4(7) . . . . ? C25 C24 C29 C28 -6.9(10) . . . . ? C27 C28 C29 N2 -178.6(7) . . . . ? C33 C28 C29 N2 57.7(10) . . . . ? C27 C28 C29 C24 7.2(10) . . . . ? C33 C28 C29 C24 -116.5(8) . . . . ? C24 C25 C30 C27 -83.0(7) . . . . ? C26 C25 C30 C27 27.8(6) . . . . ? C28 C27 C30 C25 85.8(7) . . . . ? C26 C27 C30 C25 -27.3(6) . . . . ? C29 C28 C33 C34 -76.2(10) . . . . ? C27 C28 C33 C34 160.9(7) . . . . ? C28 C33 C34 C35 114.9(10) . . . . ? C28 C33 C34 Cu1 32.2(9) . . . . ? N2 Cu1 C34 C35 -110.1(6) . . . . ? N1 Cu1 C34 C35 -28.3(8) . . . . ? C14 Cu1 C34 C35 93.3(7) . . . . ? C15 Cu1 C34 C35 130.2(6) . . . . ? N2 Cu1 C34 C33 12.9(6) . . . . ? N1 Cu1 C34 C33 94.8(7) . . . . ? C14 Cu1 C34 C33 -143.7(6) . . . . ? C15 Cu1 C34 C33 -106.8(6) . . . . ? C35 Cu1 C34 C33 123.0(10) . . . . ? C33 C34 C35 Cu1 -102.2(9) . . . . ? N2 Cu1 C35 C34 75.2(6) . . . . ? N1 Cu1 C35 C34 162.1(5) . . . . ? C14 Cu1 C35 C34 -95.6(6) . . . . ? C15 Cu1 C35 C34 -61.8(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O43 H43 F4 0.84 2.56 3.14(2) 127.4 4_645 O53 H53 O63 0.84 2.11 2.871(15) 150.7 . O63 H63 O43 0.84 2.13 2.69(2) 124.3 4_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.431 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.061