# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Jack Harrowfield' _publ_contact_author_email HARROWFIELD@ISIS.U-STRASBG.FR _publ_section_title ; Functionalised Azetidines as Ligands: Species derived by Selective Alkylation at Substituent-Nitrogen ; loop_ _publ_author_name 'Jack Harrowfield' 'Jong Seung Kim.' 'Yang Kim.' 'Young Hoon Lee.' ; Min Hee Lee ; 'Woo Taik Lim.' 'Yu Cheol Park.' P.Thuery # Attachment 'yk49.cif' data_yk49 _database_code_depnum_ccdc_archive 'CCDC 678926' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H72 Cu4 F24 N12 O8 P4' _chemical_formula_weight 1827.30 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3003(6) _cell_length_b 12.6293(5) _cell_length_c 15.2026(10) _cell_angle_alpha 69.109(4) _cell_angle_beta 84.125(3) _cell_angle_gamma 69.732(4) _cell_volume 1732.72(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 56531 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.905 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and six \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 56531 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6522 _reflns_number_gt 5482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The two PF6 ions are very badly resolved, probably due to unresolved disorder, and they have been refined with restraints on displacement parameters for the F atoms. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. The higher residual electron density peaks are located near the PF6 ions. 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^)+(0.1459P)^2^+6.1984P] 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 6522 _refine_ls_number_parameters 516 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.2310 _refine_ls_wR_factor_gt 0.2193 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.006 _refine_diff_density_min -1.724 _refine_diff_density_rms 0.239 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 0.90084(7) 0.12841(6) 0.13874(5) 0.0267(2) Uani 1 1 d . . . O1A O 0.8908(4) 0.2086(4) 0.0011(3) 0.0295(9) Uani 1 1 d . . . O2A O 0.9188(4) 0.3707(4) -0.1122(3) 0.0312(9) Uani 1 1 d . . . N1A N 0.9823(6) 0.2509(5) 0.1384(4) 0.0333(12) Uani 1 1 d . . . H1A H 1.0759 0.2147 0.1439 0.040 Uiso 1 1 calc R . . N2A N 0.8522(6) 0.1176(5) 0.2719(4) 0.0331(12) Uani 1 1 d . . . N3A N 0.7837(5) 0.0308(4) 0.1411(3) 0.0259(10) Uani 1 1 d . . . C1A C 0.9192(6) 0.3053(5) -0.0274(4) 0.0271(12) Uani 1 1 d . . . C2A C 0.9517(7) 0.3495(6) 0.0460(4) 0.0327(13) Uani 1 1 d . . . H2A H 1.0309 0.3767 0.0269 0.039 Uiso 1 1 calc R . . H2B H 0.8733 0.4168 0.0512 0.039 Uiso 1 1 calc R . . C3A C 0.9366(9) 0.2845(7) 0.2226(5) 0.0443(17) Uani 1 1 d . . . H3A H 0.8444 0.3438 0.2118 0.053 Uiso 1 1 calc R . . H3B H 0.9991 0.3188 0.2372 0.053 Uiso 1 1 calc R . . C4A C 0.9364(9) 0.1718(7) 0.3033(5) 0.0441(17) Uani 1 1 d . . . H4A H 1.0301 0.1161 0.3191 0.053 Uiso 1 1 calc R . . H4B H 0.8968 0.1914 0.3585 0.053 Uiso 1 1 calc R . . C5A C 0.6972(7) 0.1713(6) 0.2680(5) 0.0325(13) Uani 1 1 d . . . H5A H 0.6592 0.2255 0.2059 0.039 Uiso 1 1 calc R . . H5B H 0.6598 0.2079 0.3155 0.039 Uiso 1 1 calc R . . C6A C 0.8400(7) -0.0013(6) 0.3344(4) 0.0329(13) Uani 1 1 d . . . H6A H 0.8443 -0.0151 0.4012 0.039 Uiso 1 1 calc R . . H6B H 0.9027 -0.0696 0.3192 0.039 Uiso 1 1 calc R . . C7A C 0.6889(6) 0.0439(5) 0.2932(4) 0.0295(13) Uani 1 1 d . . . C8A C 0.5798(8) 0.0156(6) 0.3641(5) 0.0388(15) Uani 1 1 d . . . H8A H 0.4894 0.0610 0.3353 0.058 Uiso 1 1 calc R . . H8B H 0.5879 0.0367 0.4175 0.058 Uiso 1 1 calc R . . H8C H 0.5931 -0.0687 0.3842 0.058 Uiso 1 1 calc R . . C9A C 0.6906(6) 0.0083(5) 0.2077(4) 0.0274(12) Uani 1 1 d . . . C10A C 0.6032(6) -0.0520(6) 0.1990(5) 0.0316(13) Uani 1 1 d . . . H10A H 0.5355 -0.0640 0.2432 0.038 Uiso 1 1 calc R . . C11A C 0.6183(7) -0.0931(6) 0.1248(5) 0.0347(14) Uani 1 1 d . . . H11A H 0.5610 -0.1331 0.1184 0.042 Uiso 1 1 calc R . . C12A C 0.7214(7) -0.0741(6) 0.0584(5) 0.0326(13) Uani 1 1 d . . . H12A H 0.7361 -0.1035 0.0089 0.039 Uiso 1 1 calc R . . C13A C 0.7990(6) -0.0110(5) 0.0693(4) 0.0284(12) Uani 1 1 d . . . H13A H 0.8656 0.0039 0.0250 0.034 Uiso 1 1 calc R . . Cu2 Cu 0.84261(7) 0.35212(6) -0.23045(5) 0.0279(2) Uani 1 1 d . . . O1B O 0.9337(4) 0.1809(4) -0.2112(3) 0.0294(9) Uani 1 1 d . . . O2B O 0.8954(4) 0.0048(4) -0.1544(3) 0.0332(10) Uani 1 1 d . . . N1B N 0.6777(5) 0.3050(5) -0.1737(4) 0.0290(11) Uani 1 1 d . . . H1B H 0.6676 0.3083 -0.1145 0.035 Uiso 1 1 calc R . . N2B N 0.7040(6) 0.5185(5) -0.2854(4) 0.0339(12) Uani 1 1 d . . . N3B N 0.9923(6) 0.4083(5) -0.3089(4) 0.0319(11) Uani 1 1 d . . . C1B C 0.8566(6) 0.1159(6) -0.1777(4) 0.0286(12) Uani 1 1 d . . . C2B C 0.7036(6) 0.1798(6) -0.1673(5) 0.0310(13) Uani 1 1 d . . . H2C H 0.6504 0.1799 -0.2164 0.037 Uiso 1 1 calc R . . H2D H 0.6731 0.1366 -0.1070 0.037 Uiso 1 1 calc R . . C3B C 0.5552(7) 0.3964(6) -0.2323(5) 0.0394(15) Uani 1 1 d . . . H3C H 0.4702 0.3899 -0.2005 0.047 Uiso 1 1 calc R . . H3D H 0.5548 0.3860 -0.2925 0.047 Uiso 1 1 calc R . . C4B C 0.5684(7) 0.5184(6) -0.2464(6) 0.0409(16) Uani 1 1 d . . . H4C H 0.4958 0.5823 -0.2891 0.049 Uiso 1 1 calc R . . H4D H 0.5595 0.5315 -0.1866 0.049 Uiso 1 1 calc R . . C5B C 0.7584(7) 0.6130(6) -0.2843(5) 0.0361(14) Uani 1 1 d . . . H5C H 0.8237 0.5867 -0.2329 0.043 Uiso 1 1 calc R . . H5D H 0.6868 0.6886 -0.2878 0.043 Uiso 1 1 calc R . . C6B C 0.7206(7) 0.5540(6) -0.3896(5) 0.0385(15) Uani 1 1 d . . . H6C H 0.6374 0.6113 -0.4256 0.046 Uiso 1 1 calc R . . H6D H 0.7598 0.4864 -0.4117 0.046 Uiso 1 1 calc R . . C7B C 0.8282(7) 0.6123(6) -0.3805(5) 0.0355(14) Uani 1 1 d . . . C8B C 0.8134(9) 0.7363(7) -0.4522(5) 0.0474(18) Uani 1 1 d . . . H8D H 0.8678 0.7717 -0.4316 0.071 Uiso 1 1 calc R . . H8E H 0.7179 0.7863 -0.4581 0.071 Uiso 1 1 calc R . . H8F H 0.8450 0.7290 -0.5121 0.071 Uiso 1 1 calc R . . C9B C 0.9750(7) 0.5234(6) -0.3665(4) 0.0320(13) Uani 1 1 d . . . C10B C 1.0878(8) 0.5570(6) -0.4076(5) 0.0384(15) Uani 1 1 d . . . H10B H 1.0750 0.6359 -0.4465 0.046 Uiso 1 1 calc R . . C11B C 1.2193(8) 0.4730(7) -0.3907(5) 0.0402(15) Uani 1 1 d . . . H11B H 1.2954 0.4948 -0.4182 0.048 Uiso 1 1 calc R . . C12B C 1.2367(7) 0.3562(6) -0.3322(5) 0.0394(15) Uani 1 1 d . . . H12B H 1.3242 0.2980 -0.3197 0.047 Uiso 1 1 calc R . . C13B C 1.1210(7) 0.3283(6) -0.2931(5) 0.0356(14) Uani 1 1 d . . . H13B H 1.1327 0.2499 -0.2536 0.043 Uiso 1 1 calc R . . P1 P 0.3907(2) 0.3154(2) 0.03433(16) 0.0632(7) Uani 1 1 d . . . P2 P 0.3220(2) 0.78647(19) 0.45106(13) 0.0418(5) Uani 1 1 d . . . F1 F 0.5192(13) 0.3687(9) 0.0058(8) 0.074(3) Uani 1 1 d U . . F2 F 0.4548(5) 0.2497(5) 0.1354(4) 0.0698(15) Uani 1 1 d U . . F3 F 0.3042(11) 0.2308(9) 0.0794(8) 0.112(3) Uani 1 1 d U . . F4 F 0.2976(10) 0.3484(10) -0.0585(6) 0.102(3) Uani 1 1 d U . . F5 F 0.2989(10) 0.4211(7) 0.0690(5) 0.099(3) Uani 1 1 d U . . F6 F 0.4906(6) 0.2132(5) -0.0003(4) 0.0697(15) Uani 1 1 d U . . F7 F 0.3228(12) 0.8817(8) 0.3490(5) 0.058(2) Uani 1 1 d U . . F8 F 0.4560(10) 0.6921(12) 0.4328(7) 0.128(3) Uani 1 1 d U . . F9 F 0.3197(6) 0.6968(5) 0.5536(3) 0.0655(14) Uani 1 1 d U . . F10 F 0.2190(11) 0.8947(8) 0.4691(7) 0.097(3) Uani 1 1 d U . . F11 F 0.2443(7) 0.7308(6) 0.4073(4) 0.0848(19) Uani 1 1 d U . . F12 F 0.4434(9) 0.8051(8) 0.5037(6) 0.102(2) Uani 1 1 d U . . 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 0.0292(4) 0.0298(4) 0.0242(4) -0.0087(3) 0.0012(3) -0.0144(3) O1A 0.034(2) 0.030(2) 0.027(2) -0.0088(17) 0.0008(17) -0.0145(18) O2A 0.034(2) 0.029(2) 0.030(2) -0.0063(18) -0.0014(17) -0.0130(18) N1A 0.039(3) 0.036(3) 0.028(3) -0.008(2) -0.003(2) -0.018(2) N2A 0.041(3) 0.036(3) 0.027(3) -0.011(2) -0.001(2) -0.019(2) N3A 0.028(2) 0.025(2) 0.022(2) -0.0061(19) -0.0010(19) -0.009(2) C1A 0.024(3) 0.027(3) 0.032(3) -0.011(2) 0.000(2) -0.009(2) C2A 0.040(3) 0.032(3) 0.030(3) -0.008(3) 0.000(3) -0.018(3) C3A 0.063(5) 0.054(4) 0.032(4) -0.016(3) 0.005(3) -0.039(4) C4A 0.067(5) 0.050(4) 0.029(3) -0.013(3) -0.001(3) -0.036(4) C5A 0.040(3) 0.031(3) 0.029(3) -0.013(3) 0.003(3) -0.012(3) C6A 0.039(3) 0.032(3) 0.028(3) -0.009(3) 0.002(3) -0.014(3) C7A 0.032(3) 0.029(3) 0.027(3) -0.010(2) 0.005(2) -0.010(2) C8A 0.046(4) 0.042(4) 0.030(3) -0.012(3) 0.011(3) -0.019(3) C9A 0.026(3) 0.026(3) 0.029(3) -0.007(2) 0.003(2) -0.009(2) C10A 0.028(3) 0.034(3) 0.032(3) -0.009(3) 0.002(2) -0.013(2) C11A 0.034(3) 0.035(3) 0.041(4) -0.014(3) 0.002(3) -0.019(3) C12A 0.033(3) 0.033(3) 0.033(3) -0.012(3) 0.002(3) -0.012(3) C13A 0.030(3) 0.033(3) 0.024(3) -0.011(2) 0.003(2) -0.013(2) Cu2 0.0268(4) 0.0265(4) 0.0283(4) -0.0071(3) 0.0002(3) -0.0088(3) O1B 0.026(2) 0.030(2) 0.032(2) -0.0093(18) 0.0017(17) -0.0110(17) O2B 0.028(2) 0.026(2) 0.044(3) -0.0090(19) 0.0012(18) -0.0091(17) N1B 0.026(2) 0.030(3) 0.030(3) -0.012(2) 0.000(2) -0.007(2) N2B 0.035(3) 0.030(3) 0.035(3) -0.009(2) -0.001(2) -0.009(2) N3B 0.039(3) 0.030(3) 0.028(3) -0.009(2) 0.002(2) -0.013(2) C1B 0.027(3) 0.034(3) 0.028(3) -0.011(2) 0.000(2) -0.014(3) C2B 0.026(3) 0.034(3) 0.035(3) -0.013(3) 0.002(2) -0.012(2) C3B 0.028(3) 0.039(4) 0.050(4) -0.017(3) -0.004(3) -0.007(3) C4B 0.030(3) 0.034(4) 0.054(4) -0.018(3) -0.002(3) -0.002(3) C5B 0.041(4) 0.029(3) 0.037(4) -0.011(3) -0.001(3) -0.009(3) C6B 0.041(4) 0.036(3) 0.035(4) -0.008(3) -0.008(3) -0.010(3) C7B 0.045(4) 0.030(3) 0.029(3) -0.006(3) -0.003(3) -0.012(3) C8B 0.059(5) 0.036(4) 0.040(4) -0.003(3) -0.003(3) -0.017(3) C9B 0.041(3) 0.031(3) 0.024(3) -0.006(2) -0.001(2) -0.015(3) C10B 0.053(4) 0.037(4) 0.027(3) -0.007(3) 0.004(3) -0.022(3) C11B 0.047(4) 0.046(4) 0.036(4) -0.015(3) 0.011(3) -0.026(3) C12B 0.038(4) 0.038(4) 0.044(4) -0.013(3) 0.007(3) -0.017(3) C13B 0.035(3) 0.033(3) 0.037(3) -0.008(3) 0.004(3) -0.013(3) P1 0.0556(13) 0.0705(15) 0.0475(12) -0.0370(12) -0.0129(10) 0.0192(11) P2 0.0562(11) 0.0510(11) 0.0342(9) -0.0211(8) 0.0161(8) -0.0346(9) F1 0.113(6) 0.056(5) 0.083(6) -0.040(4) 0.062(5) -0.067(4) F2 0.048(3) 0.085(3) 0.054(3) -0.019(3) -0.006(2) 0.002(2) F3 0.100(5) 0.142(6) 0.121(6) -0.062(5) 0.020(5) -0.059(5) F4 0.100(5) 0.120(6) 0.067(4) -0.040(4) -0.008(4) -0.005(4) F5 0.132(6) 0.058(4) 0.039(3) -0.023(3) 0.006(4) 0.055(4) F6 0.060(3) 0.077(3) 0.086(4) -0.054(3) 0.021(3) -0.017(2) F7 0.142(6) 0.051(4) 0.009(3) -0.012(3) 0.021(4) -0.069(4) F8 0.078(5) 0.192(7) 0.099(5) -0.085(5) 0.000(4) 0.008(5) F9 0.101(4) 0.054(3) 0.043(3) -0.008(2) -0.015(2) -0.032(3) F10 0.096(5) 0.082(5) 0.098(5) -0.035(4) -0.006(4) -0.008(4) F11 0.115(4) 0.109(4) 0.060(3) -0.017(3) -0.011(3) -0.082(4) F12 0.108(5) 0.119(5) 0.098(4) -0.039(4) -0.004(4) -0.056(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 Cu1 O1A 1.969(4) . ? Cu1 N3A 1.992(5) . ? Cu1 N1A 1.997(5) . ? Cu1 N2A 2.002(5) . ? Cu1 O2B 2.159(4) 2_755 ? O1A C1A 1.269(7) . ? O2A C1A 1.259(7) . ? O2A Cu2 2.149(4) . ? N1A C3A 1.472(9) . ? N1A C2A 1.481(8) . ? N2A C4A 1.475(8) . ? N2A C5A 1.502(8) . ? N2A C6A 1.504(8) . ? N3A C9A 1.345(8) . ? N3A C13A 1.347(8) . ? C1A C2A 1.523(9) . ? C3A C4A 1.513(10) . ? C5A C7A 1.546(8) . ? C6A C7A 1.572(9) . ? C7A C9A 1.516(9) . ? C7A C8A 1.518(9) . ? C9A C10A 1.406(9) . ? C10A C11A 1.376(9) . ? C11A C12A 1.410(9) . ? C12A C13A 1.365(9) . ? Cu2 O1B 1.959(4) . ? Cu2 N1B 2.004(5) . ? Cu2 N2B 2.016(5) . ? Cu2 N3B 2.021(5) . ? O1B C1B 1.279(7) . ? O2B C1B 1.241(8) . ? O2B Cu1 2.159(4) 2_755 ? N1B C2B 1.477(8) . ? N1B C3B 1.486(8) . ? N2B C4B 1.461(9) . ? N2B C5B 1.491(8) . ? N2B C6B 1.494(9) . ? N3B C13B 1.342(8) . ? N3B C9B 1.362(8) . ? C1B C2B 1.522(8) . ? C3B C4B 1.530(10) . ? C5B C7B 1.563(9) . ? C6B C7B 1.568(9) . ? C7B C9B 1.520(9) . ? C7B C8B 1.521(9) . ? C9B C10B 1.388(9) . ? C10B C11B 1.381(11) . ? C11B C12B 1.383(10) . ? C12B C13B 1.376(9) . ? P1 F2 1.551(5) . ? P1 F6 1.568(5) . ? P1 F5 1.575(6) . ? P1 F3 1.555(12) . ? P1 F4 1.632(9) . ? P1 F1 1.639(10) . ? P2 F10 1.507(9) . ? P2 F8 1.556(9) . ? P2 F11 1.553(5) . ? P2 F9 1.570(5) . ? P2 F7 1.590(7) . ? P2 F12 1.674(8) . ? 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 O1A Cu1 N3A 95.66(18) . . ? O1A Cu1 N1A 84.26(19) . . ? N3A Cu1 N1A 168.5(2) . . ? O1A Cu1 N2A 155.1(2) . . ? N3A Cu1 N2A 90.4(2) . . ? N1A Cu1 N2A 85.1(2) . . ? O1A Cu1 O2B 99.93(18) . 2_755 ? N3A Cu1 O2B 100.60(18) . 2_755 ? N1A Cu1 O2B 90.7(2) . 2_755 ? N2A Cu1 O2B 102.7(2) . 2_755 ? C1A O1A Cu1 114.8(4) . . ? C1A O2A Cu2 125.9(4) . . ? C3A N1A C2A 116.9(6) . . ? C3A N1A Cu1 108.7(4) . . ? C2A N1A Cu1 109.0(4) . . ? C4A N2A C5A 120.0(6) . . ? C4A N2A C6A 120.0(5) . . ? C5A N2A C6A 89.1(5) . . ? C4A N2A Cu1 107.9(4) . . ? C5A N2A Cu1 103.7(4) . . ? C6A N2A Cu1 114.6(4) . . ? C9A N3A C13A 119.9(5) . . ? C9A N3A Cu1 123.9(4) . . ? C13A N3A Cu1 116.2(4) . . ? O2A C1A O1A 125.2(5) . . ? O2A C1A C2A 116.6(5) . . ? O1A C1A C2A 118.2(5) . . ? N1A C2A C1A 109.8(5) . . ? N1A C3A C4A 107.6(6) . . ? N2A C4A C3A 107.0(6) . . ? N2A C5A C7A 89.0(5) . . ? N2A C6A C7A 87.9(5) . . ? C9A C7A C8A 114.2(5) . . ? C9A C7A C5A 113.2(5) . . ? C8A C7A C5A 115.2(5) . . ? C9A C7A C6A 110.1(5) . . ? C8A C7A C6A 115.9(5) . . ? C5A C7A C6A 85.1(5) . . ? N3A C9A C10A 120.0(6) . . ? N3A C9A C7A 118.0(5) . . ? C10A C9A C7A 121.9(5) . . ? C11A C10A C9A 119.6(6) . . ? C10A C11A C12A 119.4(6) . . ? C13A C12A C11A 117.7(6) . . ? N3A C13A C12A 123.2(6) . . ? O1B Cu2 N1B 85.18(19) . . ? O1B Cu2 N2B 156.9(2) . . ? N1B Cu2 N2B 85.0(2) . . ? O1B Cu2 N3B 96.32(19) . . ? N1B Cu2 N3B 170.2(2) . . ? N2B Cu2 N3B 90.1(2) . . ? O1B Cu2 O2A 102.64(17) . . ? N1B Cu2 O2A 100.36(19) . . ? N2B Cu2 O2A 99.7(2) . . ? N3B Cu2 O2A 88.75(19) . . ? C1B O1B Cu2 114.9(4) . . ? C1B O2B Cu1 131.8(4) . 2_755 ? C2B N1B C3B 115.5(5) . . ? C2B N1B Cu2 108.6(4) . . ? C3B N1B Cu2 106.7(4) . . ? C4B N2B C5B 119.4(5) . . ? C4B N2B C6B 119.2(6) . . ? C5B N2B C6B 90.0(5) . . ? C4B N2B Cu2 109.0(4) . . ? C5B N2B Cu2 111.8(4) . . ? C6B N2B Cu2 105.8(4) . . ? C13B N3B C9B 118.4(6) . . ? C13B N3B Cu2 116.1(4) . . ? C9B N3B Cu2 124.9(4) . . ? O2B C1B O1B 125.5(6) . . ? O2B C1B C2B 117.0(5) . . ? O1B C1B C2B 117.5(5) . . ? N1B C2B C1B 111.3(5) . . ? N1B C3B C4B 105.7(5) . . ? N2B C4B C3B 108.2(5) . . ? N2B C5B C7B 89.0(5) . . ? N2B C6B C7B 88.7(5) . . ? C9B C7B C8B 114.5(6) . . ? C9B C7B C5B 111.6(5) . . ? C8B C7B C5B 114.6(6) . . ? C9B C7B C6B 111.6(5) . . ? C8B C7B C6B 116.4(6) . . ? C5B C7B C6B 84.7(5) . . ? N3B C9B C10B 120.7(6) . . ? N3B C9B C7B 116.9(6) . . ? C10B C9B C7B 122.4(6) . . ? C11B C10B C9B 119.9(6) . . ? C10B C11B C12B 119.3(6) . . ? C13B C12B C11B 118.2(7) . . ? N3B C13B C12B 123.5(6) . . ? F2 P1 F6 91.8(3) . . ? F2 P1 F5 87.2(4) . . ? F6 P1 F5 176.1(6) . . ? F2 P1 F3 78.5(5) . . ? F6 P1 F3 87.1(5) . . ? F5 P1 F3 96.4(6) . . ? F2 P1 F4 159.8(5) . . ? F6 P1 F4 83.9(4) . . ? F5 P1 F4 98.3(5) . . ? F3 P1 F4 81.6(6) . . ? F2 P1 F1 87.8(5) . . ? F6 P1 F1 82.7(4) . . ? F5 P1 F1 93.5(6) . . ? F3 P1 F1 162.6(7) . . ? F4 P1 F1 111.1(6) . . ? F10 P2 F8 164.6(7) . . ? F10 P2 F11 108.9(5) . . ? F8 P2 F11 85.4(5) . . ? F10 P2 F9 95.1(4) . . ? F8 P2 F9 89.5(5) . . ? F11 P2 F9 93.5(3) . . ? F10 P2 F7 82.7(5) . . ? F8 P2 F7 92.3(6) . . ? F11 P2 F7 88.2(4) . . ? F9 P2 F7 177.6(4) . . ? F10 P2 F12 88.1(5) . . ? F8 P2 F12 78.2(5) . . ? F11 P2 F12 162.3(5) . . ? F9 P2 F12 79.8(4) . . ? F7 P2 F12 98.9(5) . . ? # Attachment 'yk53.cif' data_yk53 _database_code_depnum_ccdc_archive 'CCDC 678927' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Cl2 Cu2 N8 O12' _chemical_formula_weight 978.77 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' Cl Cl 0.1484 0.1585 '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 b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.0027(3) _cell_length_b 13.6908(4) _cell_length_c 20.8482(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3996.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 56494 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.826 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 56494 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3791 _reflns_number_gt 3268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atom bound to N3 was found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0551P)^2^+4.0205P] 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 3791 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.723 _refine_diff_density_min -0.658 _refine_diff_density_rms 0.112 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 Cu Cu 0.00748(2) 0.82274(2) 0.434056(15) 0.02207(12) Uani 1 1 d . . . Cl1 Cl -0.13287(5) 1.08436(5) 0.27969(3) 0.03392(18) Uani 1 1 d . . . O1 O 0.09253(12) 0.92066(12) 0.47596(9) 0.0254(4) Uani 1 1 d . . . O2 O -0.10028(12) 0.93398(12) 0.47534(9) 0.0259(4) Uani 1 1 d . . . O3 O -0.0830(3) 1.0743(2) 0.33847(15) 0.0908(12) Uani 1 1 d . . . O4 O -0.0752(4) 1.0665(3) 0.22807(19) 0.1282(17) Uani 1 1 d . . . O5 O -0.2071(3) 1.0147(2) 0.2814(2) 0.1059(13) Uani 1 1 d . . . O6 O -0.17039(19) 1.18065(15) 0.27588(13) 0.0545(7) Uani 1 1 d . . . N1 N -0.00226(14) 0.72583(16) 0.51041(11) 0.0235(5) Uani 1 1 d . . . N2 N -0.09530(15) 0.74590(15) 0.39025(10) 0.0243(5) Uani 1 1 d . . . N3 N 0.02623(15) 0.88778(16) 0.34568(11) 0.0255(5) Uani 1 1 d . . . H3 H -0.0004 0.9478 0.3433 0.031 Uiso 1 1 d R . . N4 N 0.14988(15) 0.75650(16) 0.39496(10) 0.0252(5) Uani 1 1 d . . . C1 C 0.05567(19) 0.7428(2) 0.56098(12) 0.0272(6) Uani 1 1 d . . . H1 H 0.0946 0.7978 0.5600 0.033 Uiso 1 1 calc R . . C2 C 0.0600(2) 0.6830(2) 0.61392(13) 0.0302(6) Uani 1 1 d . . . H2 H 0.1015 0.6969 0.6475 0.036 Uiso 1 1 calc R . . C3 C 0.0015(2) 0.6020(2) 0.61603(14) 0.0309(6) Uani 1 1 d . . . H3A H 0.0025 0.5603 0.6513 0.037 Uiso 1 1 calc R . . C4 C -0.0590(2) 0.5837(2) 0.56449(13) 0.0292(6) Uani 1 1 d . . . H4 H -0.0991 0.5296 0.5653 0.035 Uiso 1 1 calc R . . C5 C -0.06013(18) 0.64555(19) 0.51197(12) 0.0237(5) Uani 1 1 d . . . C6 C -0.12526(18) 0.62849(18) 0.45474(13) 0.0246(5) Uani 1 1 d . . . C7 C -0.17671(18) 0.7240(2) 0.43437(13) 0.0265(6) Uani 1 1 d . . . H7A H -0.2369 0.7131 0.4125 0.032 Uiso 1 1 calc R . . H7B H -0.1840 0.7709 0.4689 0.032 Uiso 1 1 calc R . . C8 C -0.07024(18) 0.63947(18) 0.39014(12) 0.0247(5) Uani 1 1 d . . . H8A H -0.0023 0.6267 0.3935 0.030 Uiso 1 1 calc R . . H8B H -0.0983 0.6032 0.3549 0.030 Uiso 1 1 calc R . . C9 C -0.1890(2) 0.5391(2) 0.46067(14) 0.0307(6) Uani 1 1 d . . . H9A H -0.1502 0.4820 0.4661 0.046 Uiso 1 1 calc R . . H9B H -0.2269 0.5325 0.4225 0.046 Uiso 1 1 calc R . . H9C H -0.2303 0.5465 0.4971 0.046 Uiso 1 1 calc R . . C10 C -0.11758(19) 0.7930(2) 0.32851(13) 0.0286(6) Uani 1 1 d . . . H10A H -0.1584 0.8493 0.3353 0.034 Uiso 1 1 calc R . . H10B H -0.1506 0.7475 0.3006 0.034 Uiso 1 1 calc R . . C11 C -0.0241(2) 0.8242(2) 0.29847(14) 0.0291(6) Uani 1 1 d . . . H11A H 0.0145 0.7674 0.2885 0.035 Uiso 1 1 calc R . . H11B H -0.0360 0.8598 0.2591 0.035 Uiso 1 1 calc R . . C12 C 0.12779(19) 0.9019(2) 0.32986(13) 0.0293(6) Uani 1 1 d . . . H12A H 0.1508 0.9608 0.3506 0.035 Uiso 1 1 calc R . . H12B H 0.1344 0.9106 0.2839 0.035 Uiso 1 1 calc R . . C13 C 0.18798(18) 0.81639(18) 0.35101(12) 0.0248(5) Uani 1 1 d . . . C14 C 0.27924(19) 0.8029(2) 0.32685(14) 0.0310(6) Uani 1 1 d . . . H14 H 0.3042 0.8460 0.2967 0.037 Uiso 1 1 calc R . . C15 C 0.3326(2) 0.7246(2) 0.34802(14) 0.0347(7) Uani 1 1 d . . . H15 H 0.3935 0.7133 0.3317 0.042 Uiso 1 1 calc R . . C16 C 0.2942(2) 0.6629(2) 0.39406(14) 0.0340(7) Uani 1 1 d . . . H16 H 0.3289 0.6102 0.4097 0.041 Uiso 1 1 calc R . . C17 C 0.2032(2) 0.68183(19) 0.41611(14) 0.0284(6) Uani 1 1 d . . . H17 H 0.1775 0.6407 0.4472 0.034 Uiso 1 1 calc R . . C18 C -0.05569(18) 1.00289(18) 0.49947(12) 0.0233(5) 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 Cu 0.02196(19) 0.02146(19) 0.0228(2) -0.00002(12) 0.00041(12) -0.00061(12) Cl1 0.0450(4) 0.0260(3) 0.0308(4) 0.0019(3) -0.0040(3) 0.0039(3) O1 0.0234(9) 0.0226(9) 0.0301(10) -0.0035(7) 0.0015(7) 0.0016(7) O2 0.0229(9) 0.0220(9) 0.0328(10) -0.0031(8) 0.0011(8) -0.0005(7) O3 0.148(3) 0.0536(16) 0.0706(19) -0.0159(14) -0.062(2) 0.0486(18) O4 0.187(4) 0.104(3) 0.093(3) 0.002(2) 0.089(3) 0.042(3) O5 0.111(3) 0.067(2) 0.140(3) 0.008(2) -0.023(3) -0.044(2) O6 0.0631(16) 0.0323(12) 0.0680(17) -0.0047(11) -0.0278(13) 0.0160(11) N1 0.0224(10) 0.0238(11) 0.0242(11) -0.0007(9) 0.0011(8) 0.0009(8) N2 0.0230(10) 0.0261(11) 0.0238(11) 0.0003(9) 0.0014(9) 0.0008(9) N3 0.0256(11) 0.0222(10) 0.0287(12) 0.0018(9) 0.0003(9) 0.0012(9) N4 0.0250(11) 0.0238(11) 0.0267(11) -0.0004(9) 0.0016(9) -0.0002(9) C1 0.0258(13) 0.0278(13) 0.0279(14) -0.0022(11) -0.0001(11) 0.0005(11) C2 0.0330(15) 0.0326(14) 0.0250(14) -0.0010(11) -0.0005(11) 0.0053(12) C3 0.0424(16) 0.0255(14) 0.0248(14) 0.0009(11) 0.0017(12) 0.0042(12) C4 0.0342(15) 0.0227(13) 0.0307(14) -0.0018(11) 0.0075(12) 0.0012(11) C5 0.0222(12) 0.0231(12) 0.0259(13) -0.0012(10) 0.0055(10) 0.0015(10) C6 0.0222(12) 0.0240(13) 0.0277(13) -0.0010(10) 0.0033(11) -0.0029(10) C7 0.0218(12) 0.0282(14) 0.0294(14) -0.0003(11) 0.0025(10) -0.0017(11) C8 0.0239(12) 0.0239(12) 0.0263(13) -0.0017(11) 0.0003(10) -0.0015(10) C9 0.0293(14) 0.0290(14) 0.0338(15) -0.0011(12) 0.0032(12) -0.0056(12) C10 0.0282(13) 0.0304(14) 0.0272(14) 0.0027(11) -0.0033(11) 0.0007(11) C11 0.0319(14) 0.0307(14) 0.0245(14) 0.0023(11) -0.0023(11) -0.0014(11) C12 0.0312(14) 0.0274(13) 0.0293(14) 0.0039(11) 0.0043(11) -0.0037(11) C13 0.0248(13) 0.0270(13) 0.0225(13) -0.0045(10) 0.0001(10) -0.0038(10) C14 0.0275(14) 0.0391(15) 0.0265(14) -0.0033(12) 0.0025(11) -0.0068(12) C15 0.0242(13) 0.0461(17) 0.0339(15) -0.0105(14) 0.0004(11) 0.0031(12) C16 0.0329(15) 0.0343(15) 0.0347(15) -0.0090(13) -0.0096(12) 0.0086(12) C17 0.0321(14) 0.0252(13) 0.0280(14) -0.0019(11) -0.0024(12) 0.0020(11) C18 0.0230(13) 0.0234(13) 0.0234(13) 0.0034(10) 0.0009(10) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O1 1.9947(18) . ? Cu N2 2.003(2) . ? Cu N3 2.063(2) . ? Cu N1 2.077(2) . ? Cu O2 2.3102(18) . ? Cu N4 2.337(2) . ? Cl1 O4 1.368(3) . ? Cl1 O5 1.410(3) . ? Cl1 O3 1.417(3) . ? Cl1 O6 1.421(2) . ? O1 C18 1.274(3) 5_576 ? O2 C18 1.238(3) . ? N1 C1 1.350(3) . ? N1 C5 1.366(3) . ? N2 C10 1.473(3) . ? N2 C7 1.495(3) . ? N2 C8 1.499(3) . ? N3 C12 1.473(3) . ? N3 C11 1.492(3) . ? N3 H3 0.9041 . ? N4 C17 1.340(3) . ? N4 C13 1.340(3) . ? C1 C2 1.376(4) . ? C1 H1 0.9300 . ? C2 C3 1.380(4) . ? C2 H2 0.9300 . ? C3 C4 1.391(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.520(4) . ? C6 C9 1.519(4) . ? C6 C7 1.552(4) . ? C6 C8 1.559(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.512(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.509(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.386(4) . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.387(4) . ? C15 H15 0.9300 . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 O1 1.274(3) 5_576 ? C18 C18 1.562(5) 5_576 ? 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 O1 Cu N2 169.02(8) . . ? O1 Cu N3 91.44(8) . . ? N2 Cu N3 84.89(9) . . ? O1 Cu N1 97.63(8) . . ? N2 Cu N1 88.09(9) . . ? N3 Cu N1 165.61(9) . . ? O1 Cu O2 77.51(7) . . ? N2 Cu O2 92.69(8) . . ? N3 Cu O2 97.55(8) . . ? N1 Cu O2 95.32(7) . . ? O1 Cu N4 84.50(7) . . ? N2 Cu N4 104.49(8) . . ? N3 Cu N4 75.37(8) . . ? N1 Cu N4 94.33(8) . . ? O2 Cu N4 160.55(7) . . ? O4 Cl1 O5 109.5(3) . . ? O4 Cl1 O3 111.8(3) . . ? O5 Cl1 O3 106.0(2) . . ? O4 Cl1 O6 109.9(2) . . ? O5 Cl1 O6 110.9(2) . . ? O3 Cl1 O6 108.68(15) . . ? C18 O1 Cu 119.10(16) 5_576 . ? C18 O2 Cu 108.92(16) . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Cu 116.67(17) . . ? C5 N1 Cu 124.84(17) . . ? C10 N2 C7 117.6(2) . . ? C10 N2 C8 118.3(2) . . ? C7 N2 C8 89.09(18) . . ? C10 N2 Cu 108.72(16) . . ? C7 N2 Cu 111.88(16) . . ? C8 N2 Cu 110.07(15) . . ? C12 N3 C11 112.7(2) . . ? C12 N3 Cu 112.32(16) . . ? C11 N3 Cu 106.09(16) . . ? C12 N3 H3 105.5 . . ? C11 N3 H3 107.5 . . ? Cu N3 H3 112.9 . . ? C17 N4 C13 118.0(2) . . ? C17 N4 Cu 131.01(18) . . ? C13 N4 Cu 109.92(16) . . ? N1 C1 C2 123.4(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 120.3(2) . . ? N1 C5 C6 117.4(2) . . ? C4 C5 C6 122.3(2) . . ? C9 C6 C5 114.4(2) . . ? C9 C6 C7 115.3(2) . . ? C5 C6 C7 111.3(2) . . ? C9 C6 C8 116.0(2) . . ? C5 C6 C8 111.5(2) . . ? C7 C6 C8 84.94(18) . . ? N2 C7 C6 89.05(19) . . ? N2 C7 H7A 113.8 . . ? C6 C7 H7A 113.8 . . ? N2 C7 H7B 113.8 . . ? C6 C7 H7B 113.8 . . ? H7A C7 H7B 111.0 . . ? N2 C8 C6 88.67(18) . . ? N2 C8 H8A 113.9 . . ? C6 C8 H8A 113.9 . . ? N2 C8 H8B 113.9 . . ? C6 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 107.6(2) . . ? N2 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? N2 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N3 C11 C10 107.5(2) . . ? N3 C11 H11A 110.2 . . ? C10 C11 H11A 110.2 . . ? N3 C11 H11B 110.2 . . ? C10 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N3 C12 C13 111.8(2) . . ? N3 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N3 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? N4 C13 C14 122.3(2) . . ? N4 C13 C12 116.9(2) . . ? C14 C13 C12 120.8(2) . . ? C15 C14 C13 119.2(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 118.9(3) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 118.4(3) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? N4 C17 C16 123.2(3) . . ? N4 C17 H17 118.4 . . ? C16 C17 H17 118.4 . . ? O2 C18 O1 125.8(2) . 5_576 ? O2 C18 C18 118.1(3) . 5_576 ? O1 C18 C18 116.1(3) 5_576 5_576 ? 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 N3 H3 O3 0.90 2.08 2.981(3) 170.7 . # Attachment 'yk57.cif' data_yk57 _database_code_depnum_ccdc_archive 'CCDC 678928' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Cl0.83333 Cu F N3 O6.33333 P0.1666' _chemical_formula_weight 629.14 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 23.3386(9) _cell_length_b 23.3386(9) _cell_length_c 28.0412(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 13227.5(8) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 95447 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent dark green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5874 _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.810 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 95447 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5545 _reflns_number_gt 4314 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. The counter-ions were found to be highly disordered over several positions which have been refined with occupancy parameters chosen so as to get acceptable displacement parameters. The two PF6 ions, located on -3 axis, were affected with 0.5 occupancy parameters, as well as the ClO4 ion located on a ternary axis; the ClO4 ion in general position was hence affected with a 2/3 occupancy parameter. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints on displacement parameters for some badly behaving atoms in the counter-ions and also on one P-F bond length. The H atoms bound to N3 and O3 were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.1208P)^2^+33.6094P] 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 5545 _refine_ls_number_parameters 400 _refine_ls_number_restraints 55 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1853 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.732 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.149 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 Cu Cu 0.68787(2) 0.79095(2) 0.133766(15) 0.02808(19) Uani 1 1 d . . . P1 P 0.3333 0.6667 0.1667 0.0342(11) Uani 0.50 6 d SPU . . P2 P 1.0000 1.0000 0.0000 0.0442(13) Uani 0.50 6 d SPDU . . Cl1 Cl 1.0000 1.0000 0.1428(4) 0.061(2) Uani 0.50 3 d SPU . . Cl2 Cl 0.94500(9) 0.76896(11) 0.16550(7) 0.0516(5) Uani 0.6667 1 d P . . O1 O 0.59627(14) 0.74654(14) 0.15514(10) 0.0367(7) Uani 1 1 d . . . O2 O 0.60179(17) 0.65618(15) 0.16973(11) 0.0445(8) Uani 1 1 d . . . O3 O 0.69489(15) 0.88987(14) 0.13280(10) 0.0383(7) Uani 1 1 d . . . H3A H 0.6712 0.9077 0.1406 0.046 Uiso 1 1 d R . . H3B H 0.7368 0.9226 0.1391 0.046 Uiso 1 1 d R . . O4 O 0.9915(6) 0.9409(6) 0.1258(4) 0.099(3) Uani 0.50 1 d PU . . O5 O 1.0000 1.0000 0.1950(4) 0.052(3) Uani 0.50 3 d SP . . O6 O 0.9487(4) 0.7103(4) 0.1701(3) 0.089(2) Uani 0.667 1 d PU . . O7 O 0.9160(4) 0.7709(5) 0.1215(3) 0.102(2) Uani 0.667 1 d PU . . O8 O 0.9103(3) 0.7753(4) 0.2041(2) 0.0736(17) Uani 0.667 1 d PU . . O9 O 1.0108(2) 0.8283(3) 0.1645(2) 0.0619(16) Uani 0.666 1 d P . . N1 N 0.66338(18) 0.77623(17) 0.06194(12) 0.0324(7) Uani 1 1 d . . . N2 N 0.78177(17) 0.82282(17) 0.11575(11) 0.0330(7) Uani 1 1 d . . . N3 N 0.72016(17) 0.78581(17) 0.20093(11) 0.0310(7) Uani 1 1 d . . . H3 H 0.6894 0.7407 0.2096 0.037 Uiso 1 1 d R . . F1 F 0.3157(6) 0.7074(5) 0.1319(4) 0.049(3) Uani 0.50 1 d PU . . F2 F 0.9564(5) 1.0200(6) 0.0307(4) 0.054(3) Uani 0.50 1 d PDU . . C1 C 0.6025(2) 0.7646(2) 0.04996(16) 0.0379(10) Uani 1 1 d . . . H1 H 0.5732 0.7600 0.0742 0.045 Uiso 1 1 calc R . . C2 C 0.5819(3) 0.7595(2) 0.00316(17) 0.0454(11) Uani 1 1 d . . . H2 H 0.5396 0.7514 -0.0040 0.055 Uiso 1 1 calc R . . C3 C 0.6254(3) 0.7666(2) -0.03270(17) 0.0520(13) Uani 1 1 d . . . H3C H 0.6132 0.7642 -0.0645 0.062 Uiso 1 1 calc R . . C4 C 0.6871(3) 0.7771(2) -0.02081(16) 0.0484(12) Uani 1 1 d . . . H4 H 0.7163 0.7806 -0.0447 0.058 Uiso 1 1 calc R . . C5 C 0.7058(2) 0.7826(2) 0.02689(15) 0.0394(10) Uani 1 1 d . . . C6 C 0.7752(2) 0.8004(2) 0.04116(15) 0.0436(11) Uani 1 1 d . . . C7 C 0.7780(2) 0.7653(2) 0.08779(15) 0.0404(10) Uani 1 1 d . . . H7A H 0.7382 0.7233 0.0938 0.048 Uiso 1 1 calc R . . H7B H 0.8172 0.7613 0.0905 0.048 Uiso 1 1 calc R . . C8 C 0.8064(2) 0.8654(2) 0.07201(14) 0.0428(11) Uani 1 1 d . . . H8A H 0.8542 0.8915 0.0699 0.051 Uiso 1 1 calc R . . H8B H 0.7863 0.8926 0.0668 0.051 Uiso 1 1 calc R . . C9 C 0.8176(3) 0.7983(3) 0.00065(19) 0.0646(16) Uani 1 1 d . . . H9A H 0.7946 0.7561 -0.0150 0.097 Uiso 1 1 calc R . . H9B H 0.8587 0.8048 0.0133 0.097 Uiso 1 1 calc R . . H9C H 0.8263 0.8327 -0.0219 0.097 Uiso 1 1 calc R . . C10 C 0.8240(2) 0.8461(2) 0.15841(14) 0.0359(9) Uani 1 1 d . . . H10A H 0.8317 0.8893 0.1678 0.043 Uiso 1 1 calc R . . H10B H 0.8664 0.8493 0.1520 0.043 Uiso 1 1 calc R . . C11 C 0.7880(2) 0.7960(2) 0.19767(14) 0.0361(9) Uani 1 1 d . . . H11A H 0.7862 0.7546 0.1903 0.043 Uiso 1 1 calc R . . H11B H 0.8109 0.8124 0.2278 0.043 Uiso 1 1 calc R . . C12 C 0.7131(2) 0.8317(2) 0.23475(13) 0.0320(9) Uani 1 1 d . . . H12A H 0.6679 0.8231 0.2332 0.038 Uiso 1 1 calc R . . H12B H 0.7418 0.8768 0.2242 0.038 Uiso 1 1 calc R . . C13 C 0.7293(2) 0.8262(2) 0.28625(13) 0.0303(8) Uani 1 1 d . . . C14 C 0.7868(2) 0.8762(2) 0.30867(14) 0.0317(8) Uani 1 1 d . . . C15 C 0.8368(2) 0.9342(2) 0.28429(15) 0.0369(9) Uani 1 1 d . . . H15 H 0.8320 0.9394 0.2519 0.044 Uiso 1 1 calc R . . C16 C 0.8904(2) 0.9813(2) 0.30768(17) 0.0398(10) Uani 1 1 d . . . H16 H 0.9218 1.0181 0.2910 0.048 Uiso 1 1 calc R . . C17 C 0.9000(2) 0.9760(2) 0.35673(17) 0.0415(10) Uani 1 1 d . . . H17 H 0.9369 1.0093 0.3722 0.050 Uiso 1 1 calc R . . C18 C 0.8549(2) 0.9220(2) 0.38132(16) 0.0378(10) Uani 1 1 d . . . H18 H 0.8616 0.9184 0.4136 0.045 Uiso 1 1 calc R . . C19 C 0.79750(19) 0.8708(2) 0.35847(14) 0.0314(8) Uani 1 1 d . . . C20 C 0.7513(2) 0.8152(2) 0.38384(14) 0.0317(8) Uani 1 1 d . . . H20 H 0.7584 0.8121 0.4161 0.038 Uiso 1 1 calc R . . C21 C 0.69551(19) 0.7648(2) 0.36265(13) 0.0301(8) Uani 1 1 d . . . C22 C 0.6491(2) 0.7081(2) 0.38895(14) 0.0342(9) Uani 1 1 d . . . H22 H 0.6564 0.7048 0.4212 0.041 Uiso 1 1 calc R . . C23 C 0.5942(2) 0.6585(2) 0.36748(16) 0.0391(10) Uani 1 1 d . . . H23 H 0.5646 0.6217 0.3850 0.047 Uiso 1 1 calc R . . C24 C 0.5823(2) 0.6633(2) 0.31839(16) 0.0389(10) Uani 1 1 d . . . H24 H 0.5451 0.6292 0.3038 0.047 Uiso 1 1 calc R . . C25 C 0.6248(2) 0.7172(2) 0.29263(14) 0.0339(9) Uani 1 1 d . . . H25 H 0.6150 0.7200 0.2609 0.041 Uiso 1 1 calc R . . C26 C 0.68366(19) 0.7696(2) 0.31257(14) 0.0302(8) Uani 1 1 d . . . C27 C 0.5710(2) 0.6872(2) 0.16832(14) 0.0364(9) Uani 1 1 d . . . C28 C 0.4994(2) 0.6534(2) 0.18436(17) 0.0491(12) Uani 1 1 d . . . H28A H 0.4975 0.6615 0.2177 0.074 Uiso 1 1 calc R . . H28B H 0.4790 0.6067 0.1789 0.074 Uiso 1 1 calc R . . H28C H 0.4762 0.6707 0.1666 0.074 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 Cu 0.0315(3) 0.0300(3) 0.0242(3) 0.00066(17) -0.00092(18) 0.0165(2) P1 0.0207(13) 0.0207(13) 0.061(3) 0.000 0.000 0.0104(6) P2 0.060(2) 0.060(2) 0.0123(19) 0.000 0.000 0.0301(10) Cl1 0.063(3) 0.063(3) 0.058(4) 0.000 0.000 0.0315(13) Cl2 0.0413(9) 0.0805(13) 0.0487(10) 0.0079(9) 0.0009(7) 0.0423(10) O1 0.0359(16) 0.0316(15) 0.0392(16) 0.0007(12) 0.0007(12) 0.0144(13) O2 0.056(2) 0.0335(16) 0.0392(16) -0.0002(13) -0.0002(14) 0.0183(15) O3 0.0445(17) 0.0330(15) 0.0430(17) 0.0007(13) 0.0032(13) 0.0235(14) O4 0.098(5) 0.099(5) 0.102(5) 0.007(4) 0.004(4) 0.051(4) O5 0.061(5) 0.061(5) 0.035(6) 0.000 0.000 0.031(2) O6 0.085(4) 0.074(4) 0.111(4) 0.005(3) 0.012(3) 0.044(3) O7 0.102(4) 0.141(5) 0.086(4) -0.020(3) -0.027(3) 0.077(4) O8 0.070(3) 0.100(4) 0.066(3) 0.014(3) 0.010(3) 0.054(3) O9 0.028(2) 0.053(3) 0.093(4) -0.011(3) 0.025(3) 0.011(2) N1 0.0406(19) 0.0297(17) 0.0306(17) -0.0023(13) -0.0042(14) 0.0202(15) N2 0.0377(19) 0.0388(19) 0.0242(16) -0.0007(14) -0.0011(14) 0.0205(16) N3 0.0373(18) 0.0344(18) 0.0250(16) 0.0004(13) 0.0028(13) 0.0208(15) F1 0.053(4) 0.046(4) 0.042(4) 0.010(3) 0.000(3) 0.020(3) F2 0.057(5) 0.060(5) 0.047(4) -0.002(4) 0.001(4) 0.032(4) C1 0.045(2) 0.033(2) 0.043(2) -0.0038(18) -0.0108(19) 0.024(2) C2 0.054(3) 0.035(2) 0.048(3) -0.0061(19) -0.022(2) 0.023(2) C3 0.078(4) 0.043(3) 0.035(2) -0.009(2) -0.018(2) 0.030(3) C4 0.061(3) 0.051(3) 0.030(2) -0.004(2) -0.008(2) 0.025(3) C5 0.052(3) 0.036(2) 0.029(2) -0.0031(17) -0.0020(18) 0.021(2) C6 0.044(3) 0.057(3) 0.028(2) -0.0042(19) 0.0043(18) 0.025(2) C7 0.042(2) 0.053(3) 0.033(2) -0.0063(19) -0.0018(18) 0.029(2) C8 0.042(2) 0.050(3) 0.026(2) 0.0041(18) 0.0036(18) 0.015(2) C9 0.056(3) 0.097(5) 0.037(3) -0.013(3) 0.009(2) 0.036(3) C10 0.033(2) 0.047(2) 0.028(2) -0.0048(18) -0.0026(16) 0.0206(19) C11 0.036(2) 0.047(2) 0.030(2) -0.0021(17) -0.0003(17) 0.024(2) C12 0.036(2) 0.040(2) 0.0250(19) -0.0003(16) 0.0009(16) 0.0223(19) C13 0.033(2) 0.036(2) 0.0245(18) -0.0005(15) 0.0007(15) 0.0192(18) C14 0.032(2) 0.036(2) 0.030(2) 0.0001(16) 0.0037(16) 0.0192(18) C15 0.037(2) 0.036(2) 0.036(2) 0.0015(17) 0.0057(17) 0.0167(19) C16 0.033(2) 0.036(2) 0.049(3) 0.0000(19) 0.0077(19) 0.0166(19) C17 0.030(2) 0.041(2) 0.054(3) -0.007(2) -0.0051(19) 0.018(2) C18 0.034(2) 0.042(2) 0.041(2) -0.0071(19) -0.0081(18) 0.022(2) C19 0.029(2) 0.039(2) 0.032(2) -0.0039(16) -0.0032(16) 0.0212(18) C20 0.037(2) 0.042(2) 0.0245(18) -0.0015(16) -0.0022(16) 0.0257(19) C21 0.031(2) 0.039(2) 0.0238(18) 0.0008(16) -0.0007(15) 0.0202(18) C22 0.037(2) 0.041(2) 0.029(2) 0.0055(17) 0.0029(16) 0.0224(19) C23 0.033(2) 0.038(2) 0.042(2) 0.0080(18) 0.0055(18) 0.0141(19) C24 0.032(2) 0.041(2) 0.040(2) -0.0020(18) -0.0020(17) 0.0153(19) C25 0.032(2) 0.041(2) 0.0282(19) -0.0020(17) -0.0026(16) 0.0175(18) C26 0.031(2) 0.037(2) 0.0256(19) -0.0019(16) 0.0011(15) 0.0192(18) C27 0.045(2) 0.038(2) 0.0243(19) -0.0087(16) -0.0030(17) 0.019(2) C28 0.043(3) 0.042(3) 0.043(3) -0.008(2) 0.007(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O1 1.946(3) . ? Cu N2 1.995(3) . ? Cu N3 2.054(3) . ? Cu N1 2.075(3) . ? Cu O3 2.231(3) . ? P1 F1 1.555(10) 15 ? P1 F1 1.555(10) . ? P1 F1 1.555(11) 14_455 ? P1 F1 1.555(11) 13_565 ? P1 F1 1.555(10) 2_665 ? P1 F1 1.555(11) 3_565 ? P2 F2 1.571(8) 10_775 ? P2 F2 1.571(8) 2_765 ? P2 F2 1.571(8) 12_655 ? P2 F2 1.571(8) . ? P2 F2 1.571(8) 3_675 ? P2 F2 1.571(8) 11_565 ? Cl1 O4 1.378(12) . ? Cl1 O4 1.378(12) 2_765 ? Cl1 O4 1.378(12) 3_675 ? Cl1 O5 1.463(14) . ? Cl2 O8 1.404(6) . ? Cl2 O7 1.419(8) . ? Cl2 O6 1.420(7) . ? Cl2 O9 1.466(5) . ? O1 C27 1.259(5) . ? O2 C27 1.250(5) . ? O3 H3A 0.8703 . ? O3 H3B 0.9072 . ? N1 C1 1.350(5) . ? N1 C5 1.350(6) . ? N2 C10 1.471(5) . ? N2 C8 1.500(5) . ? N2 C7 1.518(5) . ? N3 C11 1.481(5) . ? N3 C12 1.501(5) . ? N3 H3 0.9619 . ? C1 C2 1.382(6) . ? C1 H1 0.9300 . ? C2 C3 1.379(7) . ? C2 H2 0.9300 . ? C3 C4 1.374(7) . ? C3 H3C 0.9300 . ? C4 C5 1.393(6) . ? C4 H4 0.9300 . ? C5 C6 1.510(7) . ? C6 C9 1.524(6) . ? C6 C7 1.561(6) . ? C6 C8 1.573(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.517(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.515(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.412(6) . ? C13 C26 1.420(6) . ? C14 C19 1.435(5) . ? C14 C15 1.442(6) . ? C15 C16 1.352(6) . ? C15 H15 0.9300 . ? C16 C17 1.409(7) . ? C16 H16 0.9300 . ? C17 C18 1.358(7) . ? C17 H17 0.9300 . ? C18 C19 1.426(6) . ? C18 H18 0.9300 . ? C19 C20 1.398(6) . ? C20 C21 1.378(6) . ? C20 H20 0.9300 . ? C21 C22 1.426(6) . ? C21 C26 1.447(5) . ? C22 C23 1.364(6) . ? C22 H22 0.9300 . ? C23 C24 1.420(6) . ? C23 H23 0.9300 . ? C24 C25 1.356(6) . ? C24 H24 0.9300 . ? C25 C26 1.420(6) . ? C25 H25 0.9300 . ? C27 C28 1.516(6) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 O1 Cu N2 170.31(13) . . ? O1 Cu N3 91.37(13) . . ? N2 Cu N3 83.53(13) . . ? O1 Cu N1 94.16(13) . . ? N2 Cu N1 88.63(13) . . ? N3 Cu N1 163.54(13) . . ? O1 Cu O3 92.73(12) . . ? N2 Cu O3 96.46(13) . . ? N3 Cu O3 103.43(12) . . ? N1 Cu O3 91.79(12) . . ? F1 P1 F1 95.2(6) 15 . ? F1 P1 F1 84.8(6) 15 14_455 ? F1 P1 F1 95.2(6) . 14_455 ? F1 P1 F1 84.8(6) 15 13_565 ? F1 P1 F1 179.994(3) . 13_565 ? F1 P1 F1 84.8(6) 14_455 13_565 ? F1 P1 F1 95.2(6) 15 2_665 ? F1 P1 F1 84.8(6) . 2_665 ? F1 P1 F1 179.998(3) 14_455 2_665 ? F1 P1 F1 95.2(6) 13_565 2_665 ? F1 P1 F1 179.994(2) 15 3_565 ? F1 P1 F1 84.8(6) . 3_565 ? F1 P1 F1 95.2(6) 14_455 3_565 ? F1 P1 F1 95.2(6) 13_565 3_565 ? F1 P1 F1 84.8(6) 2_665 3_565 ? F2 P2 F2 87.1(6) 10_775 2_765 ? F2 P2 F2 92.9(6) 10_775 12_655 ? F2 P2 F2 87.1(6) 2_765 12_655 ? F2 P2 F2 179.995(3) 10_775 . ? F2 P2 F2 92.9(6) 2_765 . ? F2 P2 F2 87.1(6) 12_655 . ? F2 P2 F2 87.1(6) 10_775 3_675 ? F2 P2 F2 92.9(6) 2_765 3_675 ? F2 P2 F2 179.995(2) 12_655 3_675 ? F2 P2 F2 92.9(6) . 3_675 ? F2 P2 F2 92.9(6) 10_775 11_565 ? F2 P2 F2 180.0(9) 2_765 11_565 ? F2 P2 F2 92.9(6) 12_655 11_565 ? F2 P2 F2 87.1(6) . 11_565 ? F2 P2 F2 87.1(6) 3_675 11_565 ? O4 Cl1 O4 108.6(6) . 2_765 ? O4 Cl1 O4 108.6(6) . 3_675 ? O4 Cl1 O4 108.6(6) 2_765 3_675 ? O4 Cl1 O5 110.3(6) . . ? O4 Cl1 O5 110.3(6) 2_765 . ? O4 Cl1 O5 110.3(6) 3_675 . ? O8 Cl2 O7 111.0(4) . . ? O8 Cl2 O6 110.4(4) . . ? O7 Cl2 O6 111.6(5) . . ? O8 Cl2 O9 107.6(4) . . ? O7 Cl2 O9 104.2(5) . . ? O6 Cl2 O9 111.9(4) . . ? C27 O1 Cu 117.5(3) . . ? Cu O3 H3A 139.1 . . ? Cu O3 H3B 111.1 . . ? H3A O3 H3B 102.9 . . ? C1 N1 C5 118.8(4) . . ? C1 N1 Cu 116.8(3) . . ? C5 N1 Cu 124.2(3) . . ? C10 N2 C8 117.2(3) . . ? C10 N2 C7 118.6(3) . . ? C8 N2 C7 89.8(3) . . ? C10 N2 Cu 109.9(2) . . ? C8 N2 Cu 116.1(3) . . ? C7 N2 Cu 103.5(3) . . ? C11 N3 C12 114.5(3) . . ? C11 N3 Cu 109.1(2) . . ? C12 N3 Cu 111.3(2) . . ? C11 N3 H3 110.2 . . ? C12 N3 H3 109.4 . . ? Cu N3 H3 101.5 . . ? N1 C1 C2 122.6(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.6(5) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 119.1(4) . . ? C4 C3 H3C 120.4 . . ? C2 C3 H3C 120.4 . . ? C3 C4 C5 120.2(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 120.6(4) . . ? N1 C5 C6 117.7(4) . . ? C4 C5 C6 121.6(4) . . ? C5 C6 C9 114.7(4) . . ? C5 C6 C7 113.5(4) . . ? C9 C6 C7 114.2(4) . . ? C5 C6 C8 109.1(4) . . ? C9 C6 C8 116.4(4) . . ? C7 C6 C8 85.6(3) . . ? N2 C7 C6 88.2(3) . . ? N2 C7 H7A 114.0 . . ? C6 C7 H7A 114.0 . . ? N2 C7 H7B 114.0 . . ? C6 C7 H7B 114.0 . . ? H7A C7 H7B 111.2 . . ? N2 C8 C6 88.4(3) . . ? N2 C8 H8A 113.9 . . ? C6 C8 H8A 113.9 . . ? N2 C8 H8B 113.9 . . ? C6 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 107.2(3) . . ? N2 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? N2 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? N3 C11 C10 107.8(3) . . ? N3 C11 H11A 110.2 . . ? C10 C11 H11A 110.2 . . ? N3 C11 H11B 110.2 . . ? C10 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N3 C12 C13 114.8(3) . . ? N3 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? N3 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.5 . . ? C14 C13 C26 119.9(3) . . ? C14 C13 C12 121.9(4) . . ? C26 C13 C12 118.1(4) . . ? C13 C14 C19 119.7(4) . . ? C13 C14 C15 123.6(4) . . ? C19 C14 C15 116.7(4) . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 121.7(4) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 119.6(4) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 121.1(4) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C18 121.0(4) . . ? C20 C19 C14 119.3(4) . . ? C18 C19 C14 119.6(4) . . ? C21 C20 C19 122.3(4) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 121.6(4) . . ? C20 C21 C26 119.2(4) . . ? C22 C21 C26 119.2(4) . . ? C23 C22 C21 120.9(4) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 119.9(4) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.6(4) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 122.2(4) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C13 C26 C25 123.3(4) . . ? C13 C26 C21 119.5(4) . . ? C25 C26 C21 117.1(4) . . ? O2 C27 O1 123.9(4) . . ? O2 C27 C28 119.6(4) . . ? O1 C27 C28 116.6(4) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? # Attachment 'yk58.cif' data_yk58 _database_code_depnum_ccdc_archive 'CCDC 678929' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H50 Cl3 Cu2 F6 N6 O2 P S2' _chemical_formula_weight 1017.32 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8950(6) _cell_length_b 13.1170(9) _cell_length_c 15.7629(7) _cell_angle_alpha 90.420(4) _cell_angle_beta 102.371(3) _cell_angle_gamma 105.302(3) _cell_volume 2117.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 101935 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 1.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and nine \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 101935 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.68 _reflns_number_total 8025 _reflns_number_gt 6386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. The thiophene group in molecule A was found to be disordered over two positions which have been refined with occupancy parameters constrained to sum to unity. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints on bond lengths and/or displacement parameters for some atoms in the disordered group and the solvent molecule. The H atoms bound to O and N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0387P)^2^+0.3130P] 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 8025 _refine_ls_number_parameters 527 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.388 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.064 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 0.58443(3) 0.34893(2) 0.458590(19) 0.01960(9) Uani 1 1 d . . . Cl1A Cl 0.65025(6) 0.25032(5) 0.34668(4) 0.02499(14) Uani 1 1 d . . . Cl2A Cl 0.39425(6) 0.39158(5) 0.40118(4) 0.02403(14) Uani 1 1 d . . . N1A N 0.4937(2) 0.20543(16) 0.50151(13) 0.0202(4) Uani 1 1 d . . . N2A N 0.7325(2) 0.36715(16) 0.56605(13) 0.0209(5) Uani 1 1 d . . . N3A N 0.6922(2) 0.49390(17) 0.43487(13) 0.0214(5) Uani 1 1 d . . . H3A H 0.6650 0.5437 0.4678 0.026 Uiso 1 1 d R . . C1A C 0.3798(2) 0.1496(2) 0.44964(16) 0.0233(6) Uani 1 1 d . . . H1A H 0.3478 0.1777 0.3983 0.028 Uiso 1 1 calc R . . C2A C 0.3088(3) 0.0528(2) 0.46940(17) 0.0265(6) Uani 1 1 d . . . H2A H 0.2301 0.0169 0.4325 0.032 Uiso 1 1 calc R . . C3A C 0.3568(3) 0.0102(2) 0.54533(17) 0.0276(6) Uani 1 1 d . . . H3C H 0.3108 -0.0549 0.5605 0.033 Uiso 1 1 calc R . . C4A C 0.4739(3) 0.0656(2) 0.59806(17) 0.0248(6) Uani 1 1 d . . . H4A H 0.5079 0.0375 0.6489 0.030 Uiso 1 1 calc R . . C5A C 0.5420(2) 0.1637(2) 0.57569(16) 0.0216(5) Uani 1 1 d . . . C6A C 0.6719(2) 0.2271(2) 0.63191(16) 0.0223(5) Uani 1 1 d . . . C7A C 0.7746(2) 0.2669(2) 0.57585(16) 0.0228(6) Uani 1 1 d . . . H7A1 H 0.8642 0.2774 0.6075 0.027 Uiso 1 1 calc R . . H7A2 H 0.7570 0.2248 0.5216 0.027 Uiso 1 1 calc R . . C8A C 0.6768(3) 0.3451(2) 0.64517(16) 0.0219(5) Uani 1 1 d . . . H8A1 H 0.5916 0.3576 0.6391 0.026 Uiso 1 1 calc R . . H8A2 H 0.7358 0.3802 0.6986 0.026 Uiso 1 1 calc R . . C9A C 0.7177(3) 0.1749(2) 0.71390(17) 0.0314(6) Uani 1 1 d . . . H9A1 H 0.6557 0.1676 0.7501 0.047 Uiso 1 1 calc R . . H9A2 H 0.8013 0.2179 0.7451 0.047 Uiso 1 1 calc R . . H9A3 H 0.7251 0.1062 0.6984 0.047 Uiso 1 1 calc R . . C10A C 0.8329(2) 0.4688(2) 0.56817(16) 0.0228(6) Uani 1 1 d . . . H10A H 0.9185 0.4609 0.5949 0.027 Uiso 1 1 calc R . . H10B H 0.8155 0.5229 0.6024 0.027 Uiso 1 1 calc R . . C11A C 0.8302(2) 0.5011(2) 0.47659(16) 0.0230(6) Uani 1 1 d . . . H11A H 0.8842 0.5729 0.4770 0.028 Uiso 1 1 calc R . . H11B H 0.8630 0.4542 0.4450 0.028 Uiso 1 1 calc R . . C12A C 0.6741(3) 0.5243(2) 0.34320(16) 0.0249(6) Uani 1 1 d . A . H12A H 0.5819 0.5154 0.3193 0.030 Uiso 1 1 calc R . . H12B H 0.7028 0.4769 0.3092 0.030 Uiso 1 1 calc R . . C13A C 0.7478(2) 0.6364(2) 0.33437(16) 0.0237(6) Uani 1 1 d D . . S1A S 0.70857(11) 0.74253(8) 0.37233(9) 0.0288(3) Uani 0.750(3) 1 d PU A 1 C14A C 0.8555(6) 0.6754(5) 0.2968(5) 0.0255(6) Uani 0.750(3) 1 d PDU A 1 H14A H 0.8926 0.6313 0.2703 0.031 Uiso 0.750(3) 1 calc PR A 1 S1C S 0.8685(5) 0.6654(3) 0.2869(3) 0.0251(6) Uani 0.250(3) 1 d PDU A 2 C14C C 0.7406(15) 0.7367(7) 0.3687(12) 0.0265(6) Uani 0.250(3) 1 d PDU A 2 H14C H 0.6839 0.7418 0.4040 0.032 Uiso 0.250(3) 1 calc PR A 2 C15A C 0.9028(3) 0.7870(2) 0.30266(17) 0.0340(7) Uani 1 1 d D . . H15A H 0.9736 0.8251 0.2816 0.041 Uiso 1 1 calc R A 1 C16A C 0.8297(3) 0.8294(2) 0.34320(19) 0.0400(8) Uani 1 1 d D A . H16A H 0.8455 0.9021 0.3537 0.048 Uiso 1 1 d R . . Cu2 Cu 0.47601(3) 0.32401(2) 0.055146(19) 0.02024(9) Uani 1 1 d . . . Cl1B Cl 0.63309(6) 0.47586(5) 0.10933(4) 0.02362(14) Uani 1 1 d . . . O1B O 0.45013(18) 0.23351(15) 0.17217(11) 0.0296(4) Uani 1 1 d . . . H1W H 0.3859 0.1786 0.1837 0.035 Uiso 1 1 d R . . H2W H 0.5247 0.2485 0.2220 0.035 Uiso 1 1 d R . . S1B S 0.20323(9) 0.59059(7) 0.10455(5) 0.0454(2) Uani 1 1 d . . . N1B N 0.6037(2) 0.23981(17) 0.03365(14) 0.0236(5) Uani 1 1 d . . . N2B N 0.3408(2) 0.23504(17) -0.04395(13) 0.0222(5) Uani 1 1 d . . . N3B N 0.3307(2) 0.39025(16) 0.06629(13) 0.0213(5) Uani 1 1 d . . . H3B H 0.3282 0.4424 0.0259 0.026 Uiso 1 1 d R . . C1B C 0.7217(3) 0.2637(2) 0.08902(18) 0.0288(6) Uani 1 1 d . . . H1B H 0.7378 0.3131 0.1355 0.035 Uiso 1 1 calc R . . C2B C 0.8204(3) 0.2184(2) 0.08037(19) 0.0322(7) Uani 1 1 d . . . H2B H 0.8995 0.2352 0.1212 0.039 Uiso 1 1 calc R . . C3B C 0.7983(3) 0.1482(2) 0.00990(18) 0.0286(6) Uani 1 1 d . . . H3D H 0.8639 0.1193 0.0002 0.034 Uiso 1 1 calc R . . C4B C 0.6762(3) 0.1213(2) -0.04637(17) 0.0265(6) Uani 1 1 d . . . H4B H 0.6594 0.0730 -0.0937 0.032 Uiso 1 1 calc R . . C5B C 0.5788(3) 0.16536(19) -0.03313(16) 0.0226(6) Uani 1 1 d . . . C6B C 0.4412(3) 0.1325(2) -0.08958(16) 0.0233(6) Uani 1 1 d . . . C7B C 0.3376(3) 0.1205(2) -0.03292(17) 0.0238(6) Uani 1 1 d . . . H7B1 H 0.2539 0.0713 -0.0590 0.029 Uiso 1 1 calc R . . H7B2 H 0.3685 0.1052 0.0268 0.029 Uiso 1 1 calc R . . C8B C 0.3957(3) 0.2305(2) -0.12332(16) 0.0256(6) Uani 1 1 d . . . H8B1 H 0.4669 0.2919 -0.1266 0.031 Uiso 1 1 calc R . . H8B2 H 0.3301 0.2155 -0.1775 0.031 Uiso 1 1 calc R . . C9B C 0.4160(3) 0.0408(2) -0.15646(17) 0.0306(6) Uani 1 1 d . . . H9B1 H 0.4705 0.0616 -0.1973 0.046 Uiso 1 1 calc R . . H9B2 H 0.3260 0.0218 -0.1868 0.046 Uiso 1 1 calc R . . H9B3 H 0.4357 -0.0190 -0.1275 0.046 Uiso 1 1 calc R . . C10B C 0.2168(2) 0.2648(2) -0.05645(16) 0.0236(6) Uani 1 1 d . . . H10C H 0.1438 0.2033 -0.0781 0.028 Uiso 1 1 calc R . . H10D H 0.2151 0.3181 -0.0987 0.028 Uiso 1 1 calc R . . C11B C 0.2061(2) 0.3078(2) 0.03010(16) 0.0234(6) Uani 1 1 d . . . H11C H 0.1329 0.3386 0.0222 0.028 Uiso 1 1 calc R . . H11D H 0.1927 0.2515 0.0695 0.028 Uiso 1 1 calc R . . C12B C 0.3359(3) 0.4365(2) 0.15407(16) 0.0253(6) Uani 1 1 d . . . H12C H 0.4158 0.4932 0.1720 0.030 Uiso 1 1 calc R . . H12D H 0.3383 0.3824 0.1956 0.030 Uiso 1 1 calc R . . C13B C 0.2214(3) 0.4794(2) 0.15618(17) 0.0277(6) Uani 1 1 d . . . C14B C 0.1152(3) 0.4362(2) 0.19365(17) 0.0261(6) Uani 1 1 d . . . H14B H 0.1058 0.3750 0.2238 0.031 Uiso 1 1 calc R . . C15B C 0.0253(3) 0.4958(3) 0.1805(2) 0.0523(10) Uani 1 1 d . . . H15B H -0.0501 0.4792 0.2022 0.063 Uiso 1 1 calc R . . C16B C 0.0581(4) 0.5803(3) 0.1332(2) 0.0560(11) Uani 1 1 d . . . H16B H 0.0075 0.6273 0.1180 0.067 Uiso 1 1 calc R . . P1 P 0.10507(7) 0.03871(5) 0.17696(4) 0.02418(16) Uani 1 1 d . . . F1 F 0.25904(15) 0.04624(13) 0.19115(12) 0.0387(4) Uani 1 1 d . . . F2 F 0.07196(15) -0.08619(12) 0.15359(10) 0.0319(4) Uani 1 1 d . . . F3 F -0.04621(16) 0.03058(14) 0.16313(12) 0.0441(4) Uani 1 1 d . . . F4 F 0.14195(16) 0.16376(12) 0.20054(10) 0.0346(4) Uani 1 1 d . . . F5 F 0.11324(16) 0.01744(13) 0.27729(10) 0.0352(4) Uani 1 1 d . . . F6 F 0.10032(19) 0.06028(13) 0.07684(10) 0.0446(5) Uani 1 1 d . . . O1 O 0.9522(2) 0.32158(19) 0.3562(2) 0.0776(10) Uani 1 1 d . . . H1 H 0.8661 0.3032 0.3158 0.093 Uiso 1 1 d R . . C1 C 1.0055(4) 0.2344(3) 0.3540(3) 0.0746(13) Uani 1 1 d D . . H1C H 1.0983 0.2613 0.3567 0.089 Uiso 1 1 calc R . . H1D H 0.9659 0.1939 0.2986 0.089 Uiso 1 1 calc R . . C2 C 0.9878(4) 0.1641(4) 0.4229(3) 0.0851(15) Uani 1 1 d D . . H2C H 1.0170 0.2044 0.4780 0.128 Uiso 1 1 calc R . . H2D H 1.0377 0.1139 0.4218 0.128 Uiso 1 1 calc R . . H2E H 0.8970 0.1271 0.4147 0.128 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 0.01750(16) 0.02074(17) 0.01963(16) 0.00349(12) 0.00291(12) 0.00453(12) Cl1A 0.0245(3) 0.0289(3) 0.0217(3) 0.0004(3) 0.0038(3) 0.0086(3) Cl2A 0.0197(3) 0.0261(3) 0.0262(3) 0.0033(3) 0.0027(3) 0.0080(2) N1A 0.0198(11) 0.0214(11) 0.0214(11) 0.0025(9) 0.0066(9) 0.0074(9) N2A 0.0202(11) 0.0205(11) 0.0227(11) 0.0015(9) 0.0057(9) 0.0061(9) N3A 0.0213(11) 0.0231(11) 0.0197(11) 0.0025(9) 0.0050(9) 0.0056(9) C1A 0.0226(14) 0.0238(14) 0.0241(13) -0.0005(11) 0.0049(11) 0.0076(11) C2A 0.0225(14) 0.0259(14) 0.0297(14) -0.0043(11) 0.0070(11) 0.0037(11) C3A 0.0311(15) 0.0199(14) 0.0334(15) 0.0018(11) 0.0145(12) 0.0041(11) C4A 0.0327(15) 0.0224(14) 0.0231(13) 0.0041(11) 0.0112(11) 0.0099(11) C5A 0.0232(13) 0.0228(13) 0.0216(13) 0.0005(10) 0.0072(11) 0.0094(11) C6A 0.0247(14) 0.0210(13) 0.0215(13) 0.0038(10) 0.0044(11) 0.0073(11) C7A 0.0206(13) 0.0228(13) 0.0247(13) 0.0003(11) 0.0015(11) 0.0082(11) C8A 0.0229(13) 0.0235(14) 0.0192(12) 0.0017(10) 0.0049(10) 0.0060(11) C9A 0.0343(16) 0.0274(15) 0.0290(15) 0.0079(12) 0.0018(12) 0.0067(12) C10A 0.0183(13) 0.0212(13) 0.0267(14) 0.0020(11) 0.0032(11) 0.0027(10) C11A 0.0180(13) 0.0229(14) 0.0279(14) 0.0025(11) 0.0056(11) 0.0047(10) C12A 0.0296(15) 0.0246(14) 0.0193(13) 0.0047(11) 0.0045(11) 0.0058(11) C13A 0.0254(14) 0.0246(14) 0.0193(12) 0.0045(11) 0.0012(11) 0.0066(11) S1A 0.0301(6) 0.0286(5) 0.0333(5) 0.0023(4) 0.0170(5) 0.0095(4) C14A 0.0264(9) 0.0261(8) 0.0274(9) 0.0008(7) 0.0087(7) 0.0111(7) S1C 0.0263(9) 0.0261(9) 0.0273(9) 0.0013(8) 0.0096(8) 0.0116(8) C14C 0.0274(9) 0.0273(8) 0.0294(8) 0.0013(7) 0.0121(8) 0.0109(8) C15A 0.0219(14) 0.0412(17) 0.0307(15) 0.0146(13) 0.0006(12) -0.0014(13) C16A 0.0462(19) 0.0230(15) 0.0419(18) -0.0025(13) -0.0083(15) 0.0085(14) Cu2 0.01980(16) 0.01878(16) 0.02020(16) 0.00034(12) 0.00213(12) 0.00383(12) Cl1B 0.0240(3) 0.0201(3) 0.0229(3) 0.0009(2) 0.0031(2) 0.0011(2) O1B 0.0245(10) 0.0334(11) 0.0232(9) 0.0098(8) -0.0007(8) -0.0004(8) S1B 0.0648(6) 0.0488(5) 0.0342(4) 0.0094(4) 0.0131(4) 0.0338(4) N1B 0.0246(12) 0.0203(11) 0.0247(11) 0.0020(9) 0.0043(9) 0.0053(9) N2B 0.0243(11) 0.0205(11) 0.0213(11) 0.0024(9) 0.0046(9) 0.0058(9) N3B 0.0227(11) 0.0184(11) 0.0203(11) 0.0006(9) 0.0030(9) 0.0029(9) C1B 0.0285(15) 0.0236(14) 0.0317(15) -0.0004(12) 0.0024(12) 0.0061(12) C2B 0.0242(15) 0.0273(15) 0.0430(17) 0.0053(13) 0.0023(13) 0.0075(12) C3B 0.0295(15) 0.0246(14) 0.0358(16) 0.0078(12) 0.0120(12) 0.0106(12) C4B 0.0325(16) 0.0205(14) 0.0281(14) 0.0051(11) 0.0094(12) 0.0077(12) C5B 0.0285(14) 0.0171(13) 0.0217(13) 0.0042(10) 0.0074(11) 0.0038(11) C6B 0.0283(14) 0.0191(13) 0.0216(13) 0.0012(10) 0.0058(11) 0.0046(11) C7B 0.0235(14) 0.0194(13) 0.0262(14) 0.0008(11) 0.0034(11) 0.0037(11) C8B 0.0263(14) 0.0273(14) 0.0213(13) 0.0020(11) 0.0047(11) 0.0043(11) C9B 0.0343(16) 0.0290(15) 0.0270(14) -0.0028(12) 0.0073(12) 0.0060(12) C10B 0.0210(13) 0.0215(13) 0.0248(13) -0.0004(11) -0.0003(11) 0.0043(11) C11B 0.0190(13) 0.0229(14) 0.0254(14) 0.0028(11) 0.0037(11) 0.0017(11) C12B 0.0245(14) 0.0294(15) 0.0207(13) -0.0002(11) 0.0021(11) 0.0077(11) C13B 0.0301(15) 0.0287(15) 0.0228(13) -0.0045(11) -0.0014(11) 0.0114(12) C14B 0.0295(15) 0.0199(13) 0.0283(14) -0.0106(11) 0.0134(12) 0.0007(11) C15B 0.0298(18) 0.064(3) 0.058(2) -0.033(2) 0.0065(16) 0.0070(17) C16B 0.055(2) 0.080(3) 0.0405(19) -0.0217(19) -0.0125(17) 0.049(2) P1 0.0248(4) 0.0221(4) 0.0236(3) 0.0049(3) 0.0041(3) 0.0039(3) F1 0.0249(9) 0.0306(9) 0.0597(11) 0.0026(8) 0.0139(8) 0.0025(7) F2 0.0325(9) 0.0218(8) 0.0354(9) 0.0017(7) 0.0036(7) 0.0003(7) F3 0.0261(9) 0.0461(11) 0.0573(11) 0.0060(9) -0.0006(8) 0.0130(8) F4 0.0469(10) 0.0238(8) 0.0336(9) 0.0031(7) 0.0121(8) 0.0078(7) F5 0.0437(10) 0.0363(9) 0.0234(8) 0.0080(7) 0.0075(7) 0.0070(8) F6 0.0738(13) 0.0325(10) 0.0246(8) 0.0067(7) 0.0100(8) 0.0105(9) O1 0.0379(14) 0.0358(14) 0.161(3) -0.0063(16) 0.0334(17) 0.0049(11) C1 0.064(3) 0.062(3) 0.116(4) 0.011(3) 0.049(3) 0.025(2) C2 0.064(3) 0.124(4) 0.090(3) 0.031(3) 0.029(3) 0.054(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 N2A 2.036(2) . ? Cu1 N3A 2.038(2) . ? Cu1 N1A 2.074(2) . ? Cu1 Cl2A 2.2893(7) . ? Cu1 Cl1A 2.5095(7) . ? N1A C1A 1.350(3) . ? N1A C5A 1.357(3) . ? N2A C10A 1.480(3) . ? N2A C8A 1.498(3) . ? N2A C7A 1.501(3) . ? N3A C11A 1.484(3) . ? N3A C12A 1.488(3) . ? N3A H3A 0.9723 . ? C1A C2A 1.377(4) . ? C1A H1A 0.9300 . ? C2A C3A 1.384(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.377(4) . ? C3A H3C 0.9300 . ? C4A C5A 1.394(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.520(4) . ? C6A C9A 1.518(3) . ? C6A C8A 1.547(3) . ? C6A C7A 1.558(4) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C9A H9A1 0.9600 . ? C9A H9A2 0.9600 . ? C9A H9A3 0.9600 . ? C10A C11A 1.504(3) . ? C10A H10A 0.9700 . ? C10A H10B 0.9700 . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A C13A 1.501(4) . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C13A C14A 1.405(6) . ? C13A C14C 1.446(9) . ? C13A S1C 1.612(5) . ? C13A S1A 1.700(3) . ? S1A C16A 1.651(4) . ? C14A C15A 1.413(6) . ? C14A H14A 0.9300 . ? S1C C15A 1.544(5) . ? C14C C16A 1.461(9) . ? C14C H14C 0.9300 . ? C15A C16A 1.341(3) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? Cu2 N2B 2.013(2) . ? Cu2 N3B 2.033(2) . ? Cu2 N1B 2.068(2) . ? Cu2 O1B 2.2293(18) . ? Cu2 Cl1B 2.2749(7) . ? O1B H1W 0.9120 . ? O1B H2W 0.9771 . ? S1B C16B 1.708(4) . ? S1B C13B 1.712(3) . ? N1B C1B 1.347(3) . ? N1B C5B 1.363(3) . ? N2B C10B 1.477(3) . ? N2B C8B 1.505(3) . ? N2B C7B 1.506(3) . ? N3B C11B 1.491(3) . ? N3B C12B 1.491(3) . ? N3B H3B 0.9398 . ? C1B C2B 1.388(4) . ? C1B H1B 0.9300 . ? C2B C3B 1.377(4) . ? C2B H2B 0.9300 . ? C3B C4B 1.387(4) . ? C3B H3D 0.9300 . ? C4B C5B 1.386(4) . ? C4B H4B 0.9300 . ? C5B C6B 1.518(4) . ? C6B C9B 1.522(3) . ? C6B C8B 1.554(4) . ? C6B C7B 1.561(4) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B H8B1 0.9700 . ? C8B H8B2 0.9700 . ? C9B H9B1 0.9600 . ? C9B H9B2 0.9600 . ? C9B H9B3 0.9600 . ? C10B C11B 1.512(4) . ? C10B H10C 0.9700 . ? C10B H10D 0.9700 . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C12B C13B 1.503(4) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C14B 1.401(4) . ? C14B C15B 1.390(4) . ? C14B H14B 0.9300 . ? C15B C16B 1.352(5) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? P1 F3 1.5901(18) . ? P1 F5 1.5957(16) . ? P1 F6 1.5977(17) . ? P1 F4 1.6029(16) . ? P1 F2 1.6038(16) . ? P1 F1 1.6202(17) . ? O1 C1 1.415(4) . ? O1 H1 0.9832 . ? C1 C2 1.442(5) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 H2C 0.9600 . ? C2 H2D 0.9600 . ? C2 H2E 0.9600 . ? 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 N2A Cu1 N3A 82.93(8) . . ? N2A Cu1 N1A 88.47(8) . . ? N3A Cu1 N1A 171.22(8) . . ? N2A Cu1 Cl2A 144.36(6) . . ? N3A Cu1 Cl2A 91.08(6) . . ? N1A Cu1 Cl2A 94.91(6) . . ? N2A Cu1 Cl1A 104.35(6) . . ? N3A Cu1 Cl1A 94.43(6) . . ? N1A Cu1 Cl1A 89.39(6) . . ? Cl2A Cu1 Cl1A 111.14(2) . . ? C1A N1A C5A 118.7(2) . . ? C1A N1A Cu1 116.39(17) . . ? C5A N1A Cu1 124.90(17) . . ? C10A N2A C8A 117.11(19) . . ? C10A N2A C7A 118.7(2) . . ? C8A N2A C7A 89.27(18) . . ? C10A N2A Cu1 110.97(15) . . ? C8A N2A Cu1 109.48(15) . . ? C7A N2A Cu1 109.37(15) . . ? C11A N3A C12A 113.2(2) . . ? C11A N3A Cu1 106.52(15) . . ? C12A N3A Cu1 117.74(15) . . ? C11A N3A H3A 107.1 . . ? C12A N3A H3A 107.3 . . ? Cu1 N3A H3A 104.2 . . ? N1A C1A C2A 123.0(2) . . ? N1A C1A H1A 118.5 . . ? C2A C1A H1A 118.5 . . ? C1A C2A C3A 118.7(2) . . ? C1A C2A H2A 120.7 . . ? C3A C2A H2A 120.7 . . ? C4A C3A C2A 118.9(3) . . ? C4A C3A H3C 120.6 . . ? C2A C3A H3C 120.6 . . ? C3A C4A C5A 120.4(2) . . ? C3A C4A H4A 119.8 . . ? C5A C4A H4A 119.8 . . ? N1A C5A C4A 120.4(2) . . ? N1A C5A C6A 117.6(2) . . ? C4A C5A C6A 122.0(2) . . ? C9A C6A C5A 114.0(2) . . ? C9A C6A C8A 115.4(2) . . ? C5A C6A C8A 111.8(2) . . ? C9A C6A C7A 115.9(2) . . ? C5A C6A C7A 111.1(2) . . ? C8A C6A C7A 85.48(19) . . ? N2A C7A C6A 88.66(18) . . ? N2A C7A H7A1 113.9 . . ? C6A C7A H7A1 113.9 . . ? N2A C7A H7A2 113.9 . . ? C6A C7A H7A2 113.9 . . ? H7A1 C7A H7A2 111.1 . . ? N2A C8A C6A 89.21(18) . . ? N2A C8A H8A1 113.8 . . ? C6A C8A H8A1 113.8 . . ? N2A C8A H8A2 113.8 . . ? C6A C8A H8A2 113.8 . . ? H8A1 C8A H8A2 111.0 . . ? C6A C9A H9A1 109.5 . . ? C6A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? C6A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N2A C10A C11A 109.00(19) . . ? N2A C10A H10A 109.9 . . ? C11A C10A H10A 109.9 . . ? N2A C10A H10B 109.9 . . ? C11A C10A H10B 109.9 . . ? H10A C10A H10B 108.3 . . ? N3A C11A C10A 107.0(2) . . ? N3A C11A H11A 110.3 . . ? C10A C11A H11A 110.3 . . ? N3A C11A H11B 110.3 . . ? C10A C11A H11B 110.3 . . ? H11A C11A H11B 108.6 . . ? N3A C12A C13A 113.2(2) . . ? N3A C12A H12A 108.9 . . ? C13A C12A H12A 108.9 . . ? N3A C12A H12B 108.9 . . ? C13A C12A H12B 108.9 . . ? H12A C12A H12B 107.8 . . ? C14A C13A C12A 130.0(3) . . ? C14C C13A C12A 131.9(5) . . ? C14C C13A S1C 105.3(5) . . ? C12A C13A S1C 122.6(2) . . ? C14A C13A S1A 107.5(3) . . ? C12A C13A S1A 122.5(2) . . ? C16A S1A C13A 93.67(14) . . ? C13A C14A C15A 114.5(5) . . ? C13A C14A H14A 122.7 . . ? C15A C14A H14A 122.7 . . ? C15A S1C C13A 97.4(3) . . ? C13A C14C C16A 114.5(8) . . ? C13A C14C H14C 122.8 . . ? C16A C14C H14C 122.8 . . ? C16A C15A C14A 109.5(3) . . ? C16A C15A S1C 119.3(3) . . ? C16A C15A H15A 125.2 . . ? C14A C15A H15A 125.2 . . ? S1C C15A H15A 115.5 . . ? C15A C16A C14C 103.1(5) . . ? C15A C16A S1A 114.8(2) . . ? C15A C16A H16A 122.7 . . ? C14C C16A H16A 133.9 . . ? S1A C16A H16A 122.5 . . ? N2B Cu2 N3B 83.95(8) . . ? N2B Cu2 N1B 88.47(8) . . ? N3B Cu2 N1B 172.09(8) . . ? N2B Cu2 O1B 104.70(8) . . ? N3B Cu2 O1B 90.84(8) . . ? N1B Cu2 O1B 88.89(8) . . ? N2B Cu2 Cl1B 151.02(6) . . ? N3B Cu2 Cl1B 92.13(6) . . ? N1B Cu2 Cl1B 95.61(6) . . ? O1B Cu2 Cl1B 104.05(5) . . ? Cu2 O1B H1W 134.0 . . ? Cu2 O1B H2W 116.9 . . ? H1W O1B H2W 108.8 . . ? C16B S1B C13B 91.74(18) . . ? C1B N1B C5B 118.3(2) . . ? C1B N1B Cu2 116.60(17) . . ? C5B N1B Cu2 125.09(17) . . ? C10B N2B C8B 116.78(19) . . ? C10B N2B C7B 118.4(2) . . ? C8B N2B C7B 88.92(18) . . ? C10B N2B Cu2 111.04(15) . . ? C8B N2B Cu2 111.23(16) . . ? C7B N2B Cu2 108.57(15) . . ? C11B N3B C12B 112.9(2) . . ? C11B N3B Cu2 105.94(15) . . ? C12B N3B Cu2 117.06(15) . . ? C11B N3B H3B 102.1 . . ? C12B N3B H3B 109.2 . . ? Cu2 N3B H3B 108.5 . . ? N1B C1B C2B 123.5(3) . . ? N1B C1B H1B 118.3 . . ? C2B C1B H1B 118.3 . . ? C3B C2B C1B 118.3(3) . . ? C3B C2B H2B 120.8 . . ? C1B C2B H2B 120.8 . . ? C2B C3B C4B 118.6(3) . . ? C2B C3B H3D 120.7 . . ? C4B C3B H3D 120.7 . . ? C5B C4B C3B 121.0(2) . . ? C5B C4B H4B 119.5 . . ? C3B C4B H4B 119.5 . . ? N1B C5B C4B 120.2(2) . . ? N1B C5B C6B 117.3(2) . . ? C4B C5B C6B 122.6(2) . . ? C5B C6B C9B 114.5(2) . . ? C5B C6B C8B 111.2(2) . . ? C9B C6B C8B 116.4(2) . . ? C5B C6B C7B 111.0(2) . . ? C9B C6B C7B 115.1(2) . . ? C8B C6B C7B 85.23(19) . . ? N2B C7B C6B 89.00(19) . . ? N2B C7B H7B1 113.8 . . ? C6B C7B H7B1 113.8 . . ? N2B C7B H7B2 113.8 . . ? C6B C7B H7B2 113.8 . . ? H7B1 C7B H7B2 111.0 . . ? N2B C8B C6B 89.31(19) . . ? N2B C8B H8B1 113.8 . . ? C6B C8B H8B1 113.8 . . ? N2B C8B H8B2 113.8 . . ? C6B C8B H8B2 113.8 . . ? H8B1 C8B H8B2 111.0 . . ? C6B C9B H9B1 109.5 . . ? C6B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 109.5 . . ? C6B C9B H9B3 109.5 . . ? H9B1 C9B H9B3 109.5 . . ? H9B2 C9B H9B3 109.5 . . ? N2B C10B C11B 108.5(2) . . ? N2B C10B H10C 110.0 . . ? C11B C10B H10C 110.0 . . ? N2B C10B H10D 110.0 . . ? C11B C10B H10D 110.0 . . ? H10C C10B H10D 108.4 . . ? N3B C11B C10B 107.2(2) . . ? N3B C11B H11C 110.3 . . ? C10B C11B H11C 110.3 . . ? N3B C11B H11D 110.3 . . ? C10B C11B H11D 110.3 . . ? H11C C11B H11D 108.5 . . ? N3B C12B C13B 112.9(2) . . ? N3B C12B H12C 109.0 . . ? C13B C12B H12C 109.0 . . ? N3B C12B H12D 109.0 . . ? C13B C12B H12D 109.0 . . ? H12C C12B H12D 107.8 . . ? C14B C13B C12B 128.0(3) . . ? C14B C13B S1B 110.7(2) . . ? C12B C13B S1B 121.3(2) . . ? C15B C14B C13B 112.0(3) . . ? C15B C14B H14B 124.0 . . ? C13B C14B H14B 124.0 . . ? C16B C15B C14B 113.5(3) . . ? C16B C15B H15B 123.3 . . ? C14B C15B H15B 123.3 . . ? C15B C16B S1B 112.1(3) . . ? C15B C16B H16B 124.0 . . ? S1B C16B H16B 124.0 . . ? F3 P1 F5 90.38(10) . . ? F3 P1 F6 90.90(10) . . ? F5 P1 F6 178.72(10) . . ? F3 P1 F4 90.91(9) . . ? F5 P1 F4 90.10(9) . . ? F6 P1 F4 89.84(9) . . ? F3 P1 F2 90.52(9) . . ? F5 P1 F2 89.95(9) . . ? F6 P1 F2 90.07(9) . . ? F4 P1 F2 178.57(10) . . ? F3 P1 F1 179.65(11) . . ? F5 P1 F1 89.48(9) . . ? F6 P1 F1 89.24(10) . . ? F4 P1 F1 89.41(9) . . ? F2 P1 F1 89.16(9) . . ? C1 O1 H1 107.8 . . ? O1 C1 C2 115.0(4) . . ? O1 C1 H1C 108.5 . . ? C2 C1 H1C 108.5 . . ? O1 C1 H1D 108.5 . . ? C2 C1 H1D 108.5 . . ? H1C C1 H1D 107.5 . . ? C1 C2 H2C 109.5 . . ? C1 C2 H2D 109.5 . . ? H2C C2 H2D 109.5 . . ? C1 C2 H2E 109.5 . . ? H2C C2 H2E 109.5 . . ? H2D C2 H2E 109.5 . . ? 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 O1 H1 Cl1A 0.98 2.43 3.144(3) 129.5 . O1B H1W F1 0.91 1.94 2.835(2) 168.5 . O1B H2W Cl1A 0.98 2.14 3.0881(18) 164.0 . # Attachment 'yk63.cif' data_yk63 _database_code_depnum_ccdc_archive 'CCDC 678930' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H35 Cl Cu F12 N6 O P2' _chemical_formula_weight 872.56 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.1843(9) _cell_length_b 20.0068(15) _cell_length_c 17.8969(11) _cell_angle_alpha 90.00 _cell_angle_beta 118.574(3) _cell_angle_gamma 90.00 _cell_volume 6975.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 81400 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3544 _exptl_absorpt_coefficient_mu 0.895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.727 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 81400 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6594 _reflns_number_gt 4985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O1 were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0589P)^2^+11.5204P] 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 6594 _refine_ls_number_parameters 472 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.928 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.069 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 Cu Cu 0.251993(19) 0.032898(19) 0.99652(2) 0.02549(12) Uani 1 1 d . . . Cl1 Cl 0.04678(5) -0.02099(5) 1.19047(6) 0.0416(2) Uani 1 1 d . . . N1 N 0.32190(14) 0.06478(14) 0.96217(17) 0.0282(6) Uani 1 1 d . . . N2 N 0.32249(13) -0.03828(14) 1.05668(17) 0.0281(6) Uani 1 1 d . . . N3 N 0.24444(13) 0.04300(14) 1.10943(17) 0.0265(6) Uani 1 1 d . . . N4 N 0.19298(14) 0.11324(14) 0.96386(18) 0.0289(6) Uani 1 1 d . . . N5 N 0.18905(13) -0.04998(14) 0.93633(17) 0.0271(6) Uani 1 1 d . . . N6 N 0.05714(15) 0.09588(15) 1.0391(2) 0.0378(7) Uani 1 1 d . . . C1 C 0.31370(18) 0.10951(18) 0.9020(2) 0.0324(8) Uani 1 1 d . . . H1 H 0.2704 0.1280 0.8689 0.039 Uiso 1 1 calc R . . C2 C 0.36620(19) 0.12913(19) 0.8870(2) 0.0384(9) Uani 1 1 d . . . H2 H 0.3583 0.1589 0.8433 0.046 Uiso 1 1 calc R . . C3 C 0.43152(19) 0.10359(19) 0.9383(2) 0.0390(9) Uani 1 1 d . . . H3 H 0.4684 0.1170 0.9309 0.047 Uiso 1 1 calc R . . C4 C 0.44055(18) 0.05778(19) 1.0008(2) 0.0352(8) Uani 1 1 d . . . H4 H 0.4840 0.0405 1.0364 0.042 Uiso 1 1 calc R . . C5 C 0.38489(17) 0.03771(17) 1.0101(2) 0.0299(7) Uani 1 1 d . . . C6 C 0.39113(16) -0.01144(18) 1.0763(2) 0.0309(8) Uani 1 1 d . . . H6A H 0.4207 -0.0480 1.0786 0.037 Uiso 1 1 calc R . . H6B H 0.4119 0.0101 1.1315 0.037 Uiso 1 1 calc R . . C7 C 0.31811(17) -0.05591(18) 1.1350(2) 0.0308(8) Uani 1 1 d . . . H7A H 0.3602 -0.0778 1.1756 0.037 Uiso 1 1 calc R . . H7B H 0.2803 -0.0866 1.1207 0.037 Uiso 1 1 calc R . . C8 C 0.30715(16) 0.00707(18) 1.1744(2) 0.0300(8) Uani 1 1 d . . . H8A H 0.3013 -0.0046 1.2232 0.036 Uiso 1 1 calc R . . H8B H 0.3469 0.0359 1.1937 0.036 Uiso 1 1 calc R . . C9 C 0.24729(17) 0.11667(17) 1.1182(2) 0.0296(7) Uani 1 1 d . . . H9A H 0.2941 0.1319 1.1392 0.036 Uiso 1 1 calc R . . H9B H 0.2324 0.1298 1.1590 0.036 Uiso 1 1 calc R . . C10 C 0.20146(17) 0.14845(17) 1.0331(2) 0.0297(7) Uani 1 1 d . . . C11 C 0.17048(19) 0.20968(18) 1.0250(2) 0.0382(9) Uani 1 1 d . . . H11 H 0.1770 0.2333 1.0730 0.046 Uiso 1 1 calc R . . C12 C 0.1294(2) 0.23565(19) 0.9441(3) 0.0455(10) Uani 1 1 d . . . H12 H 0.1080 0.2769 0.9374 0.055 Uiso 1 1 calc R . . C13 C 0.1206(2) 0.1994(2) 0.8738(3) 0.0441(10) Uani 1 1 d . . . H13 H 0.0934 0.2161 0.8192 0.053 Uiso 1 1 calc R . . C14 C 0.15270(18) 0.13842(19) 0.8856(2) 0.0365(8) Uani 1 1 d . . . H14 H 0.1464 0.1139 0.8382 0.044 Uiso 1 1 calc R . . C15 C 0.30374(17) -0.09585(17) 0.9970(2) 0.0312(8) Uani 1 1 d . . . H15A H 0.3264 -0.1360 1.0283 0.037 Uiso 1 1 calc R . . H15B H 0.3191 -0.0874 0.9554 0.037 Uiso 1 1 calc R . . C16 C 0.22677(17) -0.10617(17) 0.9518(2) 0.0298(7) Uani 1 1 d . . . C17 C 0.19660(19) -0.16798(19) 0.9272(2) 0.0359(8) Uani 1 1 d . . . H17 H 0.2237 -0.2060 0.9381 0.043 Uiso 1 1 calc R . . C18 C 0.1258(2) -0.1734(2) 0.8859(2) 0.0410(9) Uani 1 1 d . . . H18 H 0.1048 -0.2150 0.8694 0.049 Uiso 1 1 calc R . . C19 C 0.08703(18) -0.1163(2) 0.8699(2) 0.0380(9) Uani 1 1 d . . . H19 H 0.0394 -0.1187 0.8420 0.046 Uiso 1 1 calc R . . C20 C 0.12012(17) -0.05534(18) 0.8959(2) 0.0315(8) Uani 1 1 d . . . H20 H 0.0939 -0.0168 0.8850 0.038 Uiso 1 1 calc R . . C21 C 0.17771(16) 0.01209(17) 1.0938(2) 0.0252(7) Uani 1 1 d . . . H21A H 0.1838 -0.0360 1.0962 0.030 Uiso 1 1 calc R . . H21B H 0.1439 0.0230 1.0359 0.030 Uiso 1 1 calc R . . C22 C 0.14596(17) 0.02981(18) 1.1519(2) 0.0311(8) Uani 1 1 d . . . C23 C 0.09368(17) -0.02728(18) 1.1319(2) 0.0318(8) Uani 1 1 d . . . H23A H 0.1178 -0.0697 1.1451 0.038 Uiso 1 1 calc R . . H23B H 0.0614 -0.0269 1.0715 0.038 Uiso 1 1 calc R . . C24 C 0.10522(17) 0.09519(18) 1.1218(2) 0.0344(8) Uani 1 1 d . . . C25 C 0.1148(2) 0.1487(2) 1.1755(3) 0.0452(10) Uani 1 1 d . . . H25 H 0.1484 0.1472 1.2323 0.054 Uiso 1 1 calc R . . C26 C 0.0733(3) 0.2045(2) 1.1430(4) 0.0594(13) Uani 1 1 d . . . H26 H 0.0791 0.2409 1.1780 0.071 Uiso 1 1 calc R . . C27 C 0.0238(2) 0.2059(2) 1.0592(4) 0.0603(14) Uani 1 1 d . . . H27 H -0.0048 0.2427 1.0367 0.072 Uiso 1 1 calc R . . C28 C 0.0178(2) 0.1507(2) 1.0088(3) 0.0510(11) Uani 1 1 d . . . H28 H -0.0150 0.1519 0.9516 0.061 Uiso 1 1 calc R . . C29 C 0.19838(18) 0.0287(2) 1.2475(2) 0.0417(9) Uani 1 1 d . . . H29A H 0.2339 0.0608 1.2589 0.062 Uiso 1 1 calc R . . H29B H 0.2182 -0.0151 1.2630 0.062 Uiso 1 1 calc R . . H29C H 0.1757 0.0396 1.2800 0.062 Uiso 1 1 calc R . . P1 P 0.20545(6) 0.21710(6) 0.67693(8) 0.0493(3) Uani 1 1 d . . . P2 P 0.0000 0.36598(7) 0.7500 0.0331(3) Uani 1 2 d S . . P3 P 0.0000 0.33932(6) 0.2500 0.0279(3) Uani 1 2 d S . . F1 F 0.1970(2) 0.2914(2) 0.6459(3) 0.1413(19) Uani 1 1 d U . . F2 F 0.13135(14) 0.21844(18) 0.6674(2) 0.0819(9) Uani 1 1 d . . . F3 F 0.21785(14) 0.14216(13) 0.71146(18) 0.0692(8) Uani 1 1 d . . . F4 F 0.28049(16) 0.21478(17) 0.6871(3) 0.1004(12) Uani 1 1 d U . . F5 F 0.23683(18) 0.24132(16) 0.7731(2) 0.0912(11) Uani 1 1 d . . . F6 F 0.1750(2) 0.1876(3) 0.5851(2) 0.154(2) Uani 1 1 d U . . F7 F 0.02208(10) 0.42340(11) 0.70470(14) 0.0414(5) Uani 1 1 d . . . F8 F 0.07670(10) 0.36685(10) 0.82895(14) 0.0410(5) Uani 1 1 d . . . F9 F 0.02159(11) 0.31015(12) 0.70409(16) 0.0527(6) Uani 1 1 d . . . F10 F 0.04924(11) 0.33913(11) 0.35145(12) 0.0430(5) Uani 1 1 d . . . F11 F 0.06585(10) 0.33979(11) 0.23616(15) 0.0446(6) Uani 1 1 d . . . F12 F 0.0000 0.41929(14) 0.2500 0.0372(7) Uani 1 2 d S . . F13 F 0.0000 0.25943(13) 0.2500 0.0311(6) Uani 1 2 d S . . O1 O 0.1130(2) 0.3992(2) 0.6264(3) 0.0902(13) Uani 1 1 d . . . H1A H 0.0936 0.3666 0.5842 0.108 Uiso 1 1 d R . . H1B H 0.0879 0.3965 0.6535 0.108 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0257(2) 0.0256(2) 0.0263(2) 0.00261(17) 0.01326(17) 0.00289(16) Cl1 0.0364(5) 0.0532(6) 0.0415(5) 0.0018(4) 0.0237(4) -0.0014(4) N1 0.0316(14) 0.0271(15) 0.0288(15) 0.0019(12) 0.0166(13) 0.0006(12) N2 0.0277(14) 0.0285(15) 0.0294(15) 0.0038(12) 0.0146(12) 0.0010(11) N3 0.0247(13) 0.0288(15) 0.0251(14) -0.0001(11) 0.0112(12) -0.0001(11) N4 0.0317(15) 0.0293(16) 0.0294(15) 0.0008(12) 0.0177(13) 0.0015(12) N5 0.0270(14) 0.0300(15) 0.0252(14) -0.0005(12) 0.0133(12) 0.0002(11) N6 0.0317(16) 0.0293(17) 0.0465(19) -0.0033(14) 0.0140(15) 0.0030(12) C1 0.0351(18) 0.0310(19) 0.0331(18) 0.0033(15) 0.0177(16) 0.0006(15) C2 0.046(2) 0.036(2) 0.042(2) 0.0059(17) 0.0278(19) -0.0009(17) C3 0.040(2) 0.040(2) 0.048(2) 0.0015(18) 0.0300(19) -0.0046(17) C4 0.0305(18) 0.040(2) 0.037(2) -0.0001(16) 0.0183(16) 0.0012(15) C5 0.0315(17) 0.0276(18) 0.0320(18) -0.0024(14) 0.0162(15) -0.0007(14) C6 0.0275(17) 0.0322(19) 0.0344(19) 0.0047(15) 0.0159(16) 0.0012(14) C7 0.0261(16) 0.0347(19) 0.0317(18) 0.0099(15) 0.0139(15) 0.0047(14) C8 0.0230(16) 0.039(2) 0.0269(17) 0.0058(14) 0.0109(14) 0.0039(14) C9 0.0288(17) 0.0305(19) 0.0305(18) -0.0011(14) 0.0149(15) -0.0027(14) C10 0.0310(17) 0.0278(19) 0.0350(19) 0.0007(14) 0.0196(15) -0.0015(14) C11 0.045(2) 0.031(2) 0.042(2) -0.0016(16) 0.0230(18) 0.0032(16) C12 0.054(2) 0.032(2) 0.057(3) 0.0089(18) 0.031(2) 0.0131(17) C13 0.046(2) 0.044(2) 0.041(2) 0.0154(18) 0.0200(19) 0.0168(18) C14 0.0382(19) 0.040(2) 0.0310(19) 0.0054(16) 0.0167(17) 0.0082(16) C15 0.0318(18) 0.0276(19) 0.0364(19) 0.0029(15) 0.0181(16) 0.0037(14) C16 0.0313(17) 0.0323(19) 0.0270(17) 0.0011(14) 0.0149(15) -0.0005(14) C17 0.043(2) 0.032(2) 0.0312(19) -0.0006(15) 0.0168(17) -0.0004(16) C18 0.049(2) 0.036(2) 0.033(2) -0.0057(16) 0.0155(18) -0.0121(17) C19 0.0319(18) 0.052(2) 0.0280(18) -0.0029(17) 0.0122(16) -0.0087(17) C20 0.0304(17) 0.039(2) 0.0267(17) -0.0022(15) 0.0146(15) -0.0011(15) C21 0.0254(16) 0.0261(17) 0.0239(16) 0.0020(13) 0.0117(14) 0.0008(13) C22 0.0286(17) 0.039(2) 0.0260(17) -0.0034(15) 0.0130(15) -0.0041(15) C23 0.0327(17) 0.035(2) 0.0317(18) 0.0027(15) 0.0188(15) -0.0020(15) C24 0.0312(18) 0.037(2) 0.041(2) -0.0108(16) 0.0219(17) -0.0073(15) C25 0.053(2) 0.042(2) 0.059(3) -0.0195(19) 0.041(2) -0.0136(19) C26 0.073(3) 0.034(2) 0.105(4) -0.020(2) 0.070(3) -0.014(2) C27 0.049(2) 0.030(2) 0.120(5) 0.002(2) 0.055(3) 0.0052(19) C28 0.035(2) 0.034(2) 0.077(3) 0.004(2) 0.022(2) 0.0009(17) C29 0.0367(19) 0.064(3) 0.0275(18) -0.0060(18) 0.0181(16) -0.0108(18) P1 0.0507(6) 0.0548(7) 0.0499(6) 0.0101(5) 0.0301(5) 0.0066(5) P2 0.0304(7) 0.0288(7) 0.0377(7) 0.000 0.0143(6) 0.000 P3 0.0268(6) 0.0272(7) 0.0281(6) 0.000 0.0120(5) 0.000 F1 0.133(3) 0.104(3) 0.247(5) 0.115(3) 0.139(3) 0.074(2) F2 0.0525(16) 0.111(3) 0.090(2) -0.0185(19) 0.0410(16) -0.0089(16) F3 0.0756(18) 0.0480(16) 0.0714(18) -0.0036(13) 0.0250(15) -0.0173(13) F4 0.085(2) 0.080(2) 0.175(4) 0.058(2) 0.093(2) 0.0368(17) F5 0.093(2) 0.076(2) 0.080(2) -0.0401(17) 0.0217(19) -0.0052(17) F6 0.148(3) 0.253(5) 0.0412(17) 0.000(2) 0.030(2) 0.107(4) F7 0.0387(11) 0.0408(13) 0.0449(12) 0.0101(10) 0.0200(10) 0.0022(9) F8 0.0305(10) 0.0389(12) 0.0426(12) 0.0067(9) 0.0086(10) 0.0019(9) F9 0.0501(13) 0.0431(14) 0.0606(15) -0.0126(11) 0.0229(12) 0.0087(11) F10 0.0511(13) 0.0364(12) 0.0291(11) -0.0023(9) 0.0092(10) 0.0043(10) F11 0.0410(12) 0.0387(13) 0.0661(15) -0.0121(11) 0.0354(11) -0.0105(9) F12 0.0421(16) 0.0267(15) 0.0383(16) 0.000 0.0157(14) 0.000 F13 0.0302(14) 0.0265(15) 0.0346(15) 0.000 0.0139(12) 0.000 O1 0.110(3) 0.079(3) 0.127(4) 0.015(2) 0.093(3) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N4 1.977(3) . ? Cu N2 2.005(3) . ? Cu N1 2.025(3) . ? Cu N5 2.102(3) . ? Cu N3 2.116(3) . ? Cl1 C23 1.800(3) . ? N1 C1 1.345(4) . ? N1 C5 1.355(4) . ? N2 C15 1.489(4) . ? N2 C6 1.490(4) . ? N2 C7 1.493(4) . ? N3 C9 1.480(4) . ? N3 C8 1.502(4) . ? N3 C21 1.502(4) . ? N4 C14 1.348(4) . ? N4 C10 1.358(4) . ? N5 C20 1.347(4) . ? N5 C16 1.349(4) . ? N6 C24 1.349(5) . ? N6 C28 1.345(5) . ? C1 C2 1.372(5) . ? C1 H1 0.9300 . ? C2 C3 1.390(5) . ? C2 H2 0.9300 . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.494(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.510(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.378(5) . ? C11 C12 1.391(5) . ? C11 H11 0.9300 . ? C12 C13 1.383(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.514(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.375(5) . ? C17 C18 1.383(5) . ? C17 H17 0.9300 . ? C18 C19 1.375(6) . ? C18 H18 0.9300 . ? C19 C20 1.385(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.549(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C24 1.534(5) . ? C22 C29 1.542(5) . ? C22 C23 1.543(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.385(5) . ? C25 C26 1.384(6) . ? C25 H25 0.9300 . ? C26 C27 1.372(7) . ? C26 H26 0.9300 . ? C27 C28 1.390(7) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? P1 F6 1.563(4) . ? P1 F1 1.566(4) . ? P1 F2 1.570(3) . ? P1 F4 1.587(3) . ? P1 F5 1.592(3) . ? P1 F3 1.595(3) . ? P2 F9 1.590(2) 2_556 ? P2 F9 1.590(2) . ? P2 F8 1.6100(19) 2_556 ? P2 F8 1.610(2) . ? P2 F7 1.611(2) . ? P2 F7 1.611(2) 2_556 ? P3 F11 1.594(2) 2 ? P3 F11 1.594(2) . ? P3 F13 1.598(3) . ? P3 F12 1.600(3) . ? P3 F10 1.6101(19) 2 ? P3 F10 1.6101(19) . ? O1 H1A 0.9346 . ? O1 H1B 0.8968 . ? 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 N4 Cu N2 166.46(12) . . ? N4 Cu N1 98.58(11) . . ? N2 Cu N1 82.70(11) . . ? N4 Cu N5 107.83(11) . . ? N2 Cu N5 82.61(11) . . ? N1 Cu N5 120.68(11) . . ? N4 Cu N3 82.00(11) . . ? N2 Cu N3 87.29(11) . . ? N1 Cu N3 132.98(11) . . ? N5 Cu N3 103.19(11) . . ? C1 N1 C5 118.5(3) . . ? C1 N1 Cu 128.6(2) . . ? C5 N1 Cu 112.9(2) . . ? C15 N2 C6 110.6(3) . . ? C15 N2 C7 111.7(3) . . ? C6 N2 C7 112.5(3) . . ? C15 N2 Cu 106.59(19) . . ? C6 N2 Cu 108.5(2) . . ? C7 N2 Cu 106.7(2) . . ? C9 N3 C8 114.7(3) . . ? C9 N3 C21 114.7(3) . . ? C8 N3 C21 114.3(3) . . ? C9 N3 Cu 100.3(2) . . ? C8 N3 Cu 103.09(19) . . ? C21 N3 Cu 107.72(19) . . ? C14 N4 C10 119.2(3) . . ? C14 N4 Cu 128.8(2) . . ? C10 N4 Cu 111.7(2) . . ? C20 N5 C16 118.5(3) . . ? C20 N5 Cu 130.0(2) . . ? C16 N5 Cu 110.9(2) . . ? C24 N6 C28 118.1(3) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.7(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 116.2(3) . . ? C4 C5 C6 122.5(3) . . ? N2 C6 C5 110.7(3) . . ? N2 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 109.7(3) . . ? N2 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N2 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N3 C8 C7 109.4(3) . . ? N3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? N3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? N3 C9 C10 109.8(3) . . ? N3 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N3 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N4 C10 C11 121.4(3) . . ? N4 C10 C9 115.8(3) . . ? C11 C10 C9 122.8(3) . . ? C10 C11 C12 119.2(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 119.2(4) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 119.2(4) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N4 C14 C13 121.8(4) . . ? N4 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? N2 C15 C16 110.2(3) . . ? N2 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? N2 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N5 C16 C17 121.7(3) . . ? N5 C16 C15 115.3(3) . . ? C17 C16 C15 123.1(3) . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 118.9(4) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 118.9(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? N5 C20 C19 122.2(3) . . ? N5 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? N3 C21 C22 120.3(3) . . ? N3 C21 H21A 107.2 . . ? C22 C21 H21A 107.2 . . ? N3 C21 H21B 107.2 . . ? C22 C21 H21B 107.2 . . ? H21A C21 H21B 106.9 . . ? C24 C22 C29 114.0(3) . . ? C24 C22 C23 107.4(3) . . ? C29 C22 C23 109.3(3) . . ? C24 C22 C21 109.9(3) . . ? C29 C22 C21 113.4(3) . . ? C23 C22 C21 102.0(3) . . ? C22 C23 Cl1 113.2(2) . . ? C22 C23 H23A 108.9 . . ? Cl1 C23 H23A 108.9 . . ? C22 C23 H23B 108.9 . . ? Cl1 C23 H23B 108.9 . . ? H23A C23 H23B 107.8 . . ? N6 C24 C25 122.1(4) . . ? N6 C24 C22 114.7(3) . . ? C25 C24 C22 123.2(3) . . ? C26 C25 C24 118.7(4) . . ? C26 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? C27 C26 C25 120.0(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 118.2(4) . . ? C26 C27 H27 120.9 . . ? C28 C27 H27 120.9 . . ? N6 C28 C27 122.9(4) . . ? N6 C28 H28 118.5 . . ? C27 C28 H28 118.5 . . ? C22 C29 H29A 109.5 . . ? C22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? F6 P1 F1 93.9(3) . . ? F6 P1 F2 89.3(2) . . ? F1 P1 F2 90.17(19) . . ? F6 P1 F4 90.7(2) . . ? F1 P1 F4 90.58(18) . . ? F2 P1 F4 179.2(2) . . ? F6 P1 F5 175.5(3) . . ? F1 P1 F5 90.6(3) . . ? F2 P1 F5 90.36(19) . . ? F4 P1 F5 89.6(2) . . ? F6 P1 F3 87.7(2) . . ? F1 P1 F3 177.3(2) . . ? F2 P1 F3 92.06(18) . . ? F4 P1 F3 87.19(16) . . ? F5 P1 F3 87.83(18) . . ? F9 P2 F9 90.8(2) 2_556 . ? F9 P2 F8 90.46(12) 2_556 2_556 ? F9 P2 F8 90.41(12) . 2_556 ? F9 P2 F8 90.40(12) 2_556 . ? F9 P2 F8 90.46(12) . . ? F8 P2 F8 178.77(18) 2_556 . ? F9 P2 F7 179.06(14) 2_556 . ? F9 P2 F7 90.10(13) . . ? F8 P2 F7 89.93(11) 2_556 . ? F8 P2 F7 89.19(11) . . ? F9 P2 F7 90.10(13) 2_556 2_556 ? F9 P2 F7 179.07(14) . 2_556 ? F8 P2 F7 89.19(11) 2_556 2_556 ? F8 P2 F7 89.93(11) . 2_556 ? F7 P2 F7 89.06(17) . 2_556 ? F11 P3 F11 179.32(18) 2 . ? F11 P3 F13 90.34(9) 2 . ? F11 P3 F13 90.34(9) . . ? F11 P3 F12 89.66(9) 2 . ? F11 P3 F12 89.66(9) . . ? F13 P3 F12 180.0 . . ? F11 P3 F10 89.85(12) 2 2 ? F11 P3 F10 90.15(12) . 2 ? F13 P3 F10 89.87(9) . 2 ? F12 P3 F10 90.13(9) . 2 ? F11 P3 F10 90.15(12) 2 . ? F11 P3 F10 89.85(12) . . ? F13 P3 F10 89.87(9) . . ? F12 P3 F10 90.13(9) . . ? F10 P3 F10 179.74(17) 2 . ? H1A O1 H1B 103.4 . . ? 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 O1 H1A F1 0.93 2.51 2.762(5) 95.3 . O1 H1B F7 0.90 2.13 2.994(4) 161.1 . # Attachment 'yk64.cif' data_yk64 _database_code_depnum_ccdc_archive 'CCDC 678931' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Cl2 Cu N5 O8' _chemical_formula_weight 635.94 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.8189(4) _cell_length_b 11.5925(5) _cell_length_c 16.4100(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.117(2) _cell_angle_gamma 90.00 _cell_volume 2572.98(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 59156 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1308 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.762 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 59156 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4862 _reflns_number_gt 4223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0447P)^2^+1.2586P] 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 4862 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.286 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.067 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 Cu Cu 0.285529(17) 0.36448(2) 0.089097(15) 0.01823(9) Uani 1 1 d . . . Cl1 Cl 0.71754(4) 0.86842(4) 0.21070(3) 0.02338(13) Uani 1 1 d . . . Cl2 Cl 0.17721(4) 0.83349(5) 0.08587(3) 0.02512(13) Uani 1 1 d . . . O1 O 0.73034(12) 0.98442(14) 0.18617(13) 0.0401(4) Uani 1 1 d . . . O2 O 0.65453(11) 0.80562(14) 0.13169(10) 0.0280(3) Uani 1 1 d . . . O3 O 0.81273(11) 0.81287(15) 0.25014(10) 0.0340(4) Uani 1 1 d . . . O4 O 0.67172(13) 0.86972(16) 0.27322(11) 0.0372(4) Uani 1 1 d . . . O5 O 0.10589(13) 0.76182(16) 0.09983(14) 0.0471(5) Uani 1 1 d . . . O6 O 0.16929(13) 0.94939(14) 0.11383(11) 0.0373(4) Uani 1 1 d . . . O7 O 0.27435(12) 0.78895(15) 0.13633(11) 0.0375(4) Uani 1 1 d . . . O8 O 0.15804(14) 0.83481(15) -0.00781(11) 0.0394(4) Uani 1 1 d . . . N1 N 0.38840(12) 0.47882(15) 0.15771(11) 0.0202(4) Uani 1 1 d . . . N2 N 0.26001(12) 0.45165(14) -0.02802(11) 0.0201(4) Uani 1 1 d . . . N3 N 0.17634(12) 0.25627(15) 0.01370(11) 0.0195(4) Uani 1 1 d . . . N4 N 0.37356(12) 0.22411(15) 0.09861(11) 0.0194(4) Uani 1 1 d . . . N5 N 0.18740(13) 0.40414(15) 0.14345(11) 0.0217(4) Uani 1 1 d . . . C1 C 0.43564(15) 0.45886(19) 0.24626(14) 0.0244(4) Uani 1 1 d . . . H1 H 0.4132 0.3992 0.2710 0.029 Uiso 1 1 calc R . . C2 C 0.51559(16) 0.5228(2) 0.30158(15) 0.0282(5) Uani 1 1 d . . . H2 H 0.5461 0.5075 0.3625 0.034 Uiso 1 1 calc R . . C3 C 0.54910(16) 0.6102(2) 0.26384(15) 0.0288(5) Uani 1 1 d . . . H3 H 0.6050 0.6525 0.2986 0.035 Uiso 1 1 calc R . . C4 C 0.49882(16) 0.63446(19) 0.17393(16) 0.0268(5) Uani 1 1 d . . . H4 H 0.5198 0.6949 0.1487 0.032 Uiso 1 1 calc R . . C5 C 0.41731(15) 0.56923(18) 0.12113(14) 0.0211(4) Uani 1 1 d . . . C6 C 0.35939(15) 0.59350(18) 0.02193(14) 0.0217(4) Uani 1 1 d . . . C7 C 0.24587(15) 0.57540(17) -0.00884(14) 0.0209(4) Uani 1 1 d . . . H7A H 0.2232 0.5854 0.0384 0.025 Uiso 1 1 calc R . . H7B H 0.2057 0.6196 -0.0614 0.025 Uiso 1 1 calc R . . C8 C 0.35366(15) 0.48422(18) -0.03582(14) 0.0221(4) Uani 1 1 d . . . H8A H 0.3453 0.5016 -0.0963 0.027 Uiso 1 1 calc R . . H8B H 0.4073 0.4300 -0.0076 0.027 Uiso 1 1 calc R . . C9 C 0.38808(16) 0.70583(19) -0.00866(15) 0.0276(5) Uani 1 1 d . . . H9A H 0.3491 0.7160 -0.0714 0.041 Uiso 1 1 calc R . . H9B H 0.4569 0.7036 0.0025 0.041 Uiso 1 1 calc R . . H9C H 0.3764 0.7690 0.0236 0.041 Uiso 1 1 calc R . . C10 C 0.18374(16) 0.38756(18) -0.10170(13) 0.0228(4) Uani 1 1 d . . . H10A H 0.2148 0.3312 -0.1256 0.027 Uiso 1 1 calc R . . H10B H 0.1459 0.4404 -0.1493 0.027 Uiso 1 1 calc R . . C11 C 0.11549(15) 0.32707(18) -0.06688(14) 0.0222(4) Uani 1 1 d . . . H11A H 0.0773 0.3838 -0.0510 0.027 Uiso 1 1 calc R . . H11B H 0.0698 0.2775 -0.1130 0.027 Uiso 1 1 calc R . . C12 C 0.21683(15) 0.15059(17) -0.01048(14) 0.0214(4) Uani 1 1 d . . . H12A H 0.2077 0.1558 -0.0724 0.026 Uiso 1 1 calc R . . H12B H 0.1804 0.0839 -0.0047 0.026 Uiso 1 1 calc R . . C13 C 0.32501(15) 0.13431(17) 0.04778(13) 0.0203(4) Uani 1 1 d . . . C14 C 0.37211(15) 0.03193(18) 0.04477(13) 0.0233(4) Uani 1 1 d . . . H14 H 0.3363 -0.0299 0.0108 0.028 Uiso 1 1 calc R . . C15 C 0.47333(16) 0.02338(19) 0.09319(14) 0.0249(5) Uani 1 1 d . . . H15 H 0.5066 -0.0441 0.0917 0.030 Uiso 1 1 calc R . . C16 C 0.52459(15) 0.11717(19) 0.14406(14) 0.0239(5) Uani 1 1 d . . . H16 H 0.5927 0.1138 0.1765 0.029 Uiso 1 1 calc R . . C17 C 0.47268(15) 0.21500(19) 0.14558(14) 0.0222(4) Uani 1 1 d . . . H17 H 0.5069 0.2773 0.1802 0.027 Uiso 1 1 calc R . . C18 C 0.12005(15) 0.22534(19) 0.06782(14) 0.0235(4) Uani 1 1 d . . . H18A H 0.1532 0.1627 0.1081 0.028 Uiso 1 1 calc R . . H18B H 0.0543 0.1993 0.0287 0.028 Uiso 1 1 calc R . . C19 C 0.11229(15) 0.32752(18) 0.12051(13) 0.0213(4) Uani 1 1 d . . . C20 C 0.03540(16) 0.3408(2) 0.14710(14) 0.0258(5) Uani 1 1 d . . . H20 H -0.0164 0.2881 0.1294 0.031 Uiso 1 1 calc R . . C21 C 0.03723(16) 0.4336(2) 0.20032(14) 0.0279(5) Uani 1 1 d . . . H21 H -0.0117 0.4421 0.2217 0.034 Uiso 1 1 calc R . . C22 C 0.11218(16) 0.5139(2) 0.22165(14) 0.0269(5) Uani 1 1 d . . . H22 H 0.1131 0.5785 0.2556 0.032 Uiso 1 1 calc R . . C23 C 0.18562(15) 0.49696(19) 0.19181(13) 0.0237(4) Uani 1 1 d . . . H23 H 0.2356 0.5516 0.2056 0.028 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 Cu 0.01721(14) 0.01737(14) 0.01948(14) -0.00063(9) 0.00685(10) -0.00060(9) Cl1 0.0197(3) 0.0244(3) 0.0255(3) -0.0021(2) 0.0087(2) 0.00300(19) Cl2 0.0239(3) 0.0224(3) 0.0273(3) -0.0008(2) 0.0088(2) -0.0006(2) O1 0.0337(9) 0.0232(9) 0.0634(12) 0.0029(8) 0.0199(9) 0.0003(7) O2 0.0231(7) 0.0356(9) 0.0240(8) -0.0042(7) 0.0082(6) -0.0027(7) O3 0.0225(8) 0.0380(10) 0.0338(9) -0.0018(7) 0.0038(7) 0.0104(7) O4 0.0372(10) 0.0504(11) 0.0312(9) -0.0080(8) 0.0214(8) 0.0014(8) O5 0.0320(9) 0.0428(11) 0.0643(12) 0.0159(9) 0.0176(9) -0.0078(8) O6 0.0547(11) 0.0241(9) 0.0378(9) -0.0018(7) 0.0237(8) 0.0065(8) O7 0.0249(8) 0.0402(10) 0.0385(9) -0.0047(8) 0.0039(7) 0.0060(7) O8 0.0512(11) 0.0375(10) 0.0252(8) -0.0043(7) 0.0113(8) 0.0013(8) N1 0.0186(8) 0.0203(9) 0.0222(9) -0.0006(7) 0.0089(7) 0.0004(7) N2 0.0211(8) 0.0179(8) 0.0217(8) -0.0019(7) 0.0092(7) 0.0006(7) N3 0.0190(8) 0.0201(9) 0.0200(8) 0.0005(7) 0.0084(7) 0.0021(7) N4 0.0166(8) 0.0205(9) 0.0215(9) 0.0009(7) 0.0082(7) -0.0012(7) N5 0.0221(9) 0.0222(9) 0.0211(9) 0.0011(7) 0.0091(7) 0.0010(7) C1 0.0248(11) 0.0239(11) 0.0239(11) -0.0001(9) 0.0093(9) 0.0027(9) C2 0.0258(11) 0.0285(12) 0.0247(11) -0.0028(9) 0.0046(9) 0.0037(9) C3 0.0204(11) 0.0272(11) 0.0355(12) -0.0084(10) 0.0082(10) -0.0019(9) C4 0.0252(11) 0.0217(11) 0.0367(12) -0.0031(9) 0.0158(10) -0.0037(9) C5 0.0202(10) 0.0196(10) 0.0272(11) -0.0010(8) 0.0134(9) 0.0020(8) C6 0.0227(10) 0.0191(10) 0.0254(10) 0.0004(8) 0.0120(9) -0.0003(8) C7 0.0219(10) 0.0177(10) 0.0234(10) 0.0011(8) 0.0096(8) 0.0020(8) C8 0.0233(10) 0.0221(11) 0.0247(10) 0.0000(8) 0.0137(9) 0.0004(8) C9 0.0297(12) 0.0224(11) 0.0340(12) 0.0036(9) 0.0164(10) -0.0010(9) C10 0.0254(11) 0.0210(10) 0.0195(10) -0.0007(8) 0.0065(8) 0.0009(9) C11 0.0198(10) 0.0219(10) 0.0214(10) -0.0008(8) 0.0048(8) 0.0022(8) C12 0.0218(10) 0.0182(10) 0.0229(10) -0.0021(8) 0.0079(9) 0.0002(8) C13 0.0224(10) 0.0215(11) 0.0192(10) 0.0015(8) 0.0107(8) -0.0005(8) C14 0.0266(11) 0.0205(11) 0.0224(10) -0.0003(8) 0.0097(9) 0.0001(9) C15 0.0277(11) 0.0226(11) 0.0261(11) 0.0040(9) 0.0127(9) 0.0067(9) C16 0.0198(10) 0.0280(12) 0.0239(11) 0.0050(9) 0.0091(9) 0.0030(9) C17 0.0201(10) 0.0226(11) 0.0231(10) 0.0021(8) 0.0079(8) 0.0004(8) C18 0.0200(10) 0.0233(11) 0.0274(11) 0.0010(9) 0.0100(9) -0.0018(8) C19 0.0197(10) 0.0225(10) 0.0205(10) 0.0039(8) 0.0070(8) 0.0017(8) C20 0.0207(10) 0.0298(12) 0.0273(11) 0.0043(9) 0.0102(9) 0.0013(9) C21 0.0241(11) 0.0363(13) 0.0261(11) 0.0050(10) 0.0130(9) 0.0063(9) C22 0.0263(11) 0.0299(12) 0.0233(11) -0.0015(9) 0.0089(9) 0.0073(9) C23 0.0251(11) 0.0241(11) 0.0209(10) -0.0012(8) 0.0084(9) 0.0006(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.9864(17) . ? Cu N3 2.0215(17) . ? Cu N5 2.0449(17) . ? Cu N4 2.0513(17) . ? Cu N2 2.0649(17) . ? Cl1 O1 1.4383(17) . ? Cl1 O3 1.4412(15) . ? Cl1 O4 1.4434(17) . ? Cl1 O2 1.4468(15) . ? Cl2 O7 1.4319(16) . ? Cl2 O5 1.4343(17) . ? Cl2 O6 1.4399(17) . ? Cl2 O8 1.4448(17) . ? N1 C1 1.350(3) . ? N1 C5 1.361(3) . ? N2 C10 1.475(3) . ? N2 C8 1.493(3) . ? N2 C7 1.502(3) . ? N3 C12 1.488(3) . ? N3 C18 1.489(3) . ? N3 C11 1.504(2) . ? N4 C13 1.344(3) . ? N4 C17 1.356(3) . ? N5 C23 1.344(3) . ? N5 C19 1.352(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9300 . ? C2 C3 1.382(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 C6 1.525(3) . ? C6 C9 1.518(3) . ? C6 C7 1.560(3) . ? C6 C8 1.563(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.521(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.506(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.388(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 C16 1.392(3) . ? C15 H15 0.9300 . ? C16 C17 1.376(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.498(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.385(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9300 . ? C21 C22 1.380(3) . ? C21 H21 0.9300 . ? C22 C23 1.378(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? 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 N1 Cu N3 176.33(7) . . ? N1 Cu N5 96.92(7) . . ? N3 Cu N5 82.67(7) . . ? N1 Cu N4 99.75(7) . . ? N3 Cu N4 83.07(6) . . ? N5 Cu N4 133.52(7) . . ? N1 Cu N2 90.42(7) . . ? N3 Cu N2 86.43(7) . . ? N5 Cu N2 113.80(7) . . ? N4 Cu N2 109.15(7) . . ? O1 Cl1 O3 109.07(10) . . ? O1 Cl1 O4 110.07(11) . . ? O3 Cl1 O4 110.11(10) . . ? O1 Cl1 O2 109.28(10) . . ? O3 Cl1 O2 109.42(9) . . ? O4 Cl1 O2 108.87(10) . . ? O7 Cl2 O5 109.33(11) . . ? O7 Cl2 O6 110.23(10) . . ? O5 Cl2 O6 109.17(12) . . ? O7 Cl2 O8 109.46(11) . . ? O5 Cl2 O8 109.80(12) . . ? O6 Cl2 O8 108.84(10) . . ? C1 N1 C5 119.22(18) . . ? C1 N1 Cu 115.85(14) . . ? C5 N1 Cu 124.81(14) . . ? C10 N2 C8 119.00(16) . . ? C10 N2 C7 121.83(16) . . ? C8 N2 C7 89.46(14) . . ? C10 N2 Cu 107.71(12) . . ? C8 N2 Cu 112.35(12) . . ? C7 N2 Cu 105.11(12) . . ? C12 N3 C18 110.24(16) . . ? C12 N3 C11 112.16(15) . . ? C18 N3 C11 112.02(15) . . ? C12 N3 Cu 111.41(12) . . ? C18 N3 Cu 106.72(12) . . ? C11 N3 Cu 104.00(12) . . ? C13 N4 C17 118.26(18) . . ? C13 N4 Cu 113.87(13) . . ? C17 N4 Cu 127.78(14) . . ? C23 N5 C19 118.56(18) . . ? C23 N5 Cu 128.81(15) . . ? C19 N5 Cu 112.47(14) . . ? N1 C1 C2 123.0(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.0(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N1 C5 C4 119.65(19) . . ? N1 C5 C6 118.15(17) . . ? C4 C5 C6 122.19(19) . . ? C9 C6 C5 113.58(18) . . ? C9 C6 C7 114.78(17) . . ? C5 C6 C7 112.51(17) . . ? C9 C6 C8 116.61(17) . . ? C5 C6 C8 111.42(17) . . ? C7 C6 C8 84.87(15) . . ? N2 C7 C6 88.39(14) . . ? N2 C7 H7A 113.9 . . ? C6 C7 H7A 113.9 . . ? N2 C7 H7B 113.9 . . ? C6 C7 H7B 113.9 . . ? H7A C7 H7B 111.1 . . ? N2 C8 C6 88.57(15) . . ? N2 C8 H8A 113.9 . . ? C6 C8 H8A 113.9 . . ? N2 C8 H8B 113.9 . . ? C6 C8 H8B 113.9 . . ? H8A C8 H8B 111.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 109.20(16) . . ? N2 C10 H10A 109.8 . . ? C11 C10 H10A 109.8 . . ? N2 C10 H10B 109.8 . . ? C11 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N3 C11 C10 109.27(16) . . ? N3 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? N3 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? N3 C12 C13 112.01(16) . . ? N3 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N3 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? N4 C13 C14 122.33(19) . . ? N4 C13 C12 117.26(18) . . ? C14 C13 C12 120.34(18) . . ? C15 C14 C13 118.91(19) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 119.1(2) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C17 C16 C15 118.83(19) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? N4 C17 C16 122.53(19) . . ? N4 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? N3 C18 C19 110.33(17) . . ? N3 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? N3 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? N5 C19 C20 121.9(2) . . ? N5 C19 C18 115.57(18) . . ? C20 C19 C18 122.45(19) . . ? C21 C20 C19 118.7(2) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C20 C21 C22 119.5(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 119.0(2) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? N5 C23 C22 122.2(2) . . ? N5 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? # Attachment 'YK06-32.cif' data_yk0632 _database_code_depnum_ccdc_archive 'CCDC 678932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22.50 Cl0.50 Cu F6 N3 O P' _chemical_formula_weight 523.13 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' 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 11.499(2) _cell_length_b 13.853(3) _cell_length_c 15.187(3) _cell_angle_alpha 100.04(3) _cell_angle_beta 104.44(3) _cell_angle_gamma 104.47(3) _cell_volume 2195.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 53762 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 30.37 _exptl_crystal_description irregular _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.788 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Synchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7576 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 30.37 _reflns_number_total 7576 _reflns_number_gt 5512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.1343P)^2^+1.6496P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0097(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7576 _refine_ls_number_parameters 551 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.2218 _refine_ls_wR_factor_gt 0.2059 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.26443(6) 0.42549(5) 0.34886(5) 0.0574(2) Uani 1 1 d . . . Cu2 Cu 0.11491(6) 0.05263(5) 0.20311(4) 0.0589(2) Uani 1 1 d . . . Cl1 Cl 0.18309(14) 0.23890(9) 0.27666(11) 0.0748(4) Uani 1 1 d . . . O1 O 0.3912(3) 0.4416(3) 0.4686(2) 0.0634(9) Uani 1 1 d . . . H38 H 0.4665 0.4955 0.4918 0.076 Uiso 1 1 calc R . . O2 O -0.0115(3) 0.0318(2) 0.0788(2) 0.0492(7) Uani 1 1 d . . . H39 H -0.0191 -0.0158 0.0247 0.059 Uiso 1 1 calc R . . N1 N 0.3938(4) 0.4490(3) 0.2818(3) 0.0645(11) Uani 1 1 d . . . N2 N 0.1562(6) 0.4845(4) 0.2641(4) 0.0868(17) Uani 1 1 d . . . N3 N 0.1271(5) 0.4077(4) 0.4138(4) 0.0766(14) Uani 1 1 d . . . N4 N 0.2567(4) 0.0672(3) 0.1475(4) 0.0678(13) Uani 1 1 d . . . N5 N 0.2019(7) -0.0062(4) 0.3009(5) 0.105(2) Uani 1 1 d . . . N6 N -0.0218(5) 0.0340(4) 0.2651(3) 0.0789(15) Uani 1 1 d . . . H6 H -0.0044 0.0953 0.3070 0.095 Uiso 1 1 calc R . . C1 C 0.3612(5) 0.3680(4) 0.5155(4) 0.0625(13) Uani 1 1 d . . . C2 C 0.4350(6) 0.3056(5) 0.5347(5) 0.0855(19) Uani 1 1 d . . . H2 H 0.5075 0.3141 0.5162 0.103 Uiso 1 1 calc R . . C3 C 0.4032(10) 0.2305(7) 0.5809(7) 0.126(4) Uani 1 1 d . . . H3 H 0.4546 0.1892 0.5935 0.101 Uiso 1 1 calc R . . C4 C 0.2999(13) 0.2164(9) 0.6076(8) 0.151(5) Uani 1 1 d . . . H4 H 0.2799 0.1661 0.6394 0.102 Uiso 1 1 calc R . . C5 C 0.2235(9) 0.2757(8) 0.5883(6) 0.118(3) Uani 1 1 d . . . H5 H 0.1505 0.2643 0.6062 0.102 Uiso 1 1 calc R . . C6 C 0.2522(6) 0.3552(5) 0.5412(4) 0.0771(17) Uani 1 1 d . . . C7 C 0.1723(7) 0.4209(6) 0.5163(5) 0.094(2) Uani 1 1 d . . . H7A H 0.1003 0.4036 0.5395 0.103 Uiso 1 1 calc R . . H7B H 0.2203 0.4925 0.5466 0.103 Uiso 1 1 calc R . . C8 C 0.0539(7) 0.4749(7) 0.3871(6) 0.105(3) Uani 1 1 d . . . H8A H 0.0993 0.5454 0.4230 0.106 Uiso 1 1 calc R . . H8B H -0.0261 0.4543 0.3998 0.106 Uiso 1 1 calc R . . C9 C 0.0319(7) 0.4672(7) 0.2848(7) 0.113(3) Uani 1 1 d . . . H9A H -0.0068 0.5185 0.2669 0.106 Uiso 1 1 calc R . . H9B H -0.0249 0.3996 0.2486 0.106 Uiso 1 1 calc R . . C10 C 0.2405(8) 0.5910(5) 0.2760(5) 0.104(3) Uani 1 1 d . . . H10A H 0.3086 0.6174 0.3350 0.105 Uiso 1 1 calc R . . H10B H 0.1955 0.6405 0.2649 0.105 Uiso 1 1 calc R . . C11 C 0.2808(10) 0.5473(5) 0.1916(5) 0.110(3) Uani 1 1 d . . . C12 C 0.1579(8) 0.4588(5) 0.1650(5) 0.104(3) Uani 1 1 d . . . H12A H 0.0877 0.4682 0.1202 0.105 Uiso 1 1 calc R . . H12B H 0.1668 0.3913 0.1450 0.105 Uiso 1 1 calc R . . C13 C 0.2894(14) 0.6143(7) 0.1229(6) 0.168(6) Uani 1 1 d . . . H13A H 0.3145 0.5819 0.0727 0.102 Uiso 1 1 calc R . . H13B H 0.3505 0.6804 0.1549 0.102 Uiso 1 1 calc R . . H13C H 0.2085 0.6231 0.0976 0.102 Uiso 1 1 calc R . . C14 C 0.3942(8) 0.5055(5) 0.2185(4) 0.090(2) Uani 1 1 d . . . C15 C 0.4892(12) 0.5187(7) 0.1783(7) 0.130(4) Uani 1 1 d . . . H15 H 0.4924 0.5610 0.1371 0.106 Uiso 1 1 calc R . . C16 C 0.5779(12) 0.4712(10) 0.1973(9) 0.149(5) Uani 1 1 d . . . H16 H 0.6407 0.4801 0.1682 0.109 Uiso 1 1 calc R . . C17 C 0.5770(7) 0.4087(7) 0.2602(6) 0.106(3) Uani 1 1 d . . . H17 H 0.6368 0.3745 0.2736 0.107 Uiso 1 1 calc R . . C18 C 0.4829(6) 0.4008(5) 0.3007(4) 0.0741(16) Uani 1 1 d . . . H18 H 0.4796 0.3603 0.3434 0.089 Uiso 1 1 calc R . . C19 C -0.0850(4) 0.0945(4) 0.0819(3) 0.0479(10) Uani 1 1 d . . . C20 C -0.0860(5) 0.1659(4) 0.0294(4) 0.0647(13) Uani 1 1 d . . . H20 H -0.0408 0.1688 -0.0135 0.078 Uiso 1 1 calc R . . C21 C -0.1547(7) 0.2333(6) 0.0410(6) 0.094(2) Uani 1 1 d . . . H21 H -0.1543 0.2821 0.0059 0.103 Uiso 1 1 calc R . . C22 C -0.2226(7) 0.2302(7) 0.1019(7) 0.112(3) Uani 1 1 d . . . H22 H -0.2686 0.2760 0.1085 0.104 Uiso 1 1 calc R . . C23 C -0.2228(6) 0.1602(7) 0.1528(6) 0.099(3) Uani 1 1 d . . . H23 H -0.2694 0.1589 0.1949 0.109 Uiso 1 1 calc R . . C24 C -0.1550(5) 0.0883(5) 0.1452(4) 0.0683(15) Uani 1 1 d . . . C25 C -0.1531(6) 0.0125(5) 0.2008(5) 0.084(2) Uani 1 1 d . . . H25A H -0.1811 -0.0561 0.1594 0.101 Uiso 1 1 calc R . . H25B H -0.2106 0.0153 0.2377 0.101 Uiso 1 1 calc R . . C26 C -0.0057(11) -0.0410(6) 0.3216(5) 0.134(4) Uani 1 1 d . . . H26A H -0.0360 -0.1103 0.2811 0.101 Uiso 1 1 calc R . . H26B H -0.0529 -0.0381 0.3662 0.101 Uiso 1 1 calc R . . C27 C 0.1335(12) -0.0127(8) 0.3726(6) 0.149(5) Uani 1 1 d . . . H27A H 0.1615 0.0530 0.4187 0.109 Uiso 1 1 calc R . . H27B H 0.1502 -0.0646 0.4050 0.109 Uiso 1 1 calc R . . C28 C 0.2207(8) -0.0986(5) 0.2443(7) 0.126(4) Uani 1 1 d . . . H28A H 0.1610 -0.1257 0.1815 0.102 Uiso 1 1 calc R . . H28B H 0.2245 -0.1529 0.2764 0.102 Uiso 1 1 calc R . . C29 C 0.3523(7) -0.0303(6) 0.2475(8) 0.133(4) Uani 1 1 d . . . C30 C 0.3426(8) 0.0409(6) 0.3360(6) 0.127(4) Uani 1 1 d . . . H30A H 0.3820 0.0274 0.3950 0.103 Uiso 1 1 calc R . . H30B H 0.3708 0.1138 0.3388 0.103 Uiso 1 1 calc R . . C31 C 0.4573(10) -0.0805(8) 0.2668(12) 0.237(9) Uani 1 1 d . . . H31A H 0.4536 -0.1120 0.3179 0.106 Uiso 1 1 calc R . . H31B H 0.5378 -0.0289 0.2829 0.106 Uiso 1 1 calc R . . H31C H 0.4465 -0.1320 0.2116 0.106 Uiso 1 1 calc R . . C32 C 0.3496(6) 0.0233(5) 0.1681(6) 0.096(3) Uani 1 1 d . . . C33 C 0.4436(8) 0.0409(8) 0.1226(9) 0.134(5) Uani 1 1 d . . . H33 H 0.5074 0.0104 0.1350 0.101 Uiso 1 1 calc R . . C34 C 0.4425(8) 0.0995(10) 0.0634(10) 0.140(5) Uani 1 1 d . . . H34 H 0.5048 0.1091 0.0339 0.108 Uiso 1 1 calc R . . C35 C 0.3529(6) 0.1456(6) 0.0447(6) 0.100(3) Uani 1 1 d . . . H35 H 0.3539 0.1888 0.0042 0.120 Uiso 1 1 calc R . . C36 C 0.2599(5) 0.1275(5) 0.0868(4) 0.0667(14) Uani 1 1 d . . . H36 H 0.1964 0.1581 0.0730 0.080 Uiso 1 1 calc R . . P1 P 0.2438(2) 0.79464(15) 0.55709(14) 0.0905(6) Uani 1 1 d . . . P2 P 0.14490(18) 0.33421(14) -0.11394(13) 0.0833(5) Uani 1 1 d . . . F1 F 0.1394(6) 0.7560(5) 0.4593(4) 0.151(2) Uani 1 1 d . . . F2 F 0.3393(7) 0.8471(7) 0.5113(5) 0.184(3) Uani 1 1 d . . . F3 F 0.2899(8) 0.6949(5) 0.5310(6) 0.201(4) Uani 1 1 d . . . F4 F 0.1550(8) 0.7318(8) 0.5995(6) 0.244(5) Uani 1 1 d . . . F5 F 0.3477(6) 0.8322(5) 0.6545(4) 0.158(2) Uani 1 1 d . . . F6 F 0.2088(9) 0.8919(6) 0.5781(6) 0.210(4) Uani 1 1 d . . . F7 F 0.0540(10) 0.3050(6) -0.2164(4) 0.225(4) Uani 1 1 d . . . F8 F 0.0972(6) 0.2168(4) -0.1122(4) 0.1410(19) Uani 1 1 d . . . F9 F 0.2457(8) 0.3042(6) -0.1524(7) 0.206(4) Uani 1 1 d . . . F10 F 0.2230(9) 0.3544(8) -0.0136(5) 0.234(4) Uani 1 1 d . . . F11 F 0.0400(8) 0.3558(6) -0.0772(7) 0.200(3) Uani 1 1 d . . . F12 F 0.1843(8) 0.4480(4) -0.1180(6) 0.187(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 Cu1 0.0552(4) 0.0497(4) 0.0615(4) 0.0108(3) 0.0096(3) 0.0163(3) Cu2 0.0678(4) 0.0498(4) 0.0533(4) 0.0176(3) 0.0086(3) 0.0147(3) Cl1 0.0839(10) 0.0400(6) 0.0848(11) -0.0051(7) 0.0283(8) 0.0038(6) O1 0.0451(17) 0.069(2) 0.058(2) 0.0214(19) 0.0056(15) -0.0075(16) O2 0.0502(17) 0.0563(18) 0.0392(16) 0.0062(15) 0.0142(14) 0.0168(15) N1 0.072(3) 0.056(3) 0.055(3) 0.014(2) 0.017(2) 0.005(2) N2 0.095(4) 0.059(3) 0.079(4) 0.004(3) -0.016(3) 0.028(3) N3 0.059(3) 0.068(3) 0.093(4) -0.006(3) 0.022(3) 0.023(2) N4 0.043(2) 0.052(2) 0.087(3) -0.006(3) -0.002(2) 0.0157(19) N5 0.127(5) 0.056(3) 0.085(4) 0.023(3) -0.033(4) 0.010(3) N6 0.109(4) 0.056(3) 0.047(3) 0.006(2) 0.028(3) -0.015(3) C1 0.063(3) 0.058(3) 0.046(3) 0.009(3) 0.010(2) -0.009(2) C2 0.078(4) 0.090(5) 0.074(4) 0.038(4) 0.003(3) 0.011(3) C3 0.102(8) 0.086(5) 0.105(7) 0.056(5) -0.010(6) 0.005(5) C4 0.102(11) 0.130(9) 0.103(8) 0.080(7) 0.010(7) -0.022(8) C5 0.102(7) 0.125(7) 0.081(5) 0.032(5) 0.047(5) -0.028(6) C6 0.079(4) 0.081(4) 0.060(3) 0.010(3) 0.033(3) 0.000(3) C7 0.081(4) 0.103(5) 0.085(5) -0.006(4) 0.039(4) 0.014(4) C8 0.074(4) 0.101(5) 0.100(7) -0.022(5) 0.014(4) 0.040(4) C9 0.080(5) 0.108(6) 0.102(8) 0.013(6) 0.001(5) 0.057(4) C10 0.106(7) 0.057(4) 0.078(5) 0.011(4) -0.015(5) 0.030(4) C11 0.103(8) 0.056(4) 0.072(5) 0.023(4) -0.002(5) 0.022(5) C12 0.108(6) 0.066(4) 0.064(4) 0.008(4) -0.034(4) 0.024(4) C13 0.095(16) 0.090(6) 0.097(6) 0.055(5) 0.033(8) 0.045(8) C14 0.108(6) 0.049(3) 0.058(4) 0.016(3) 0.017(4) -0.005(4) C15 0.100(11) 0.096(6) 0.096(6) 0.032(5) 0.067(7) -0.019(7) C16 0.104(10) 0.148(10) 0.147(10) 0.021(8) 0.099(9) -0.011(8) C17 0.085(5) 0.121(6) 0.105(6) 0.015(5) 0.056(5) 0.004(4) C18 0.075(4) 0.073(4) 0.074(4) 0.015(3) 0.034(3) 0.015(3) C19 0.037(2) 0.050(2) 0.048(3) 0.000(2) 0.011(2) 0.0083(19) C20 0.054(3) 0.067(3) 0.065(3) 0.015(3) 0.008(2) 0.019(3) C21 0.080(4) 0.088(5) 0.100(5) 0.014(4) -0.007(4) 0.042(4) C22 0.066(4) 0.108(6) 0.107(8) -0.019(6) 0.006(5) 0.045(4) C23 0.056(4) 0.110(6) 0.105(6) -0.022(5) 0.035(4) 0.022(4) C24 0.047(3) 0.071(3) 0.072(4) -0.005(3) 0.026(3) 0.003(3) C25 0.080(4) 0.081(4) 0.074(4) 0.002(3) 0.042(4) -0.012(3) C26 0.097(11) 0.078(5) 0.057(4) 0.026(4) 0.025(6) -0.030(6) C27 0.099(12) 0.103(7) 0.077(5) 0.053(5) -0.011(7) 0.004(7) C28 0.103(7) 0.044(3) 0.109(7) 0.015(4) -0.052(6) 0.017(4) C29 0.091(5) 0.055(4) 0.104(9) -0.005(5) -0.059(6) 0.030(4) C30 0.100(7) 0.069(4) 0.106(6) 0.017(5) -0.069(5) 0.007(4) C31 0.106(8) 0.062(6) 0.090(2) 0.018(10) -0.070(11) 0.0062(6) C32 0.058(4) 0.054(3) 0.109(6) -0.021(4) -0.028(4) 0.023(3) C33 0.051(4) 0.111(7) 0.104(12) -0.035(7) -0.006(6) 0.040(5) C34 0.063(5) 0.145(10) 0.102(12) -0.032(8) 0.041(6) 0.028(6) C35 0.051(3) 0.104(5) 0.102(6) -0.020(5) 0.030(4) -0.006(3) C36 0.049(3) 0.068(3) 0.074(4) 0.009(3) 0.014(3) 0.014(3) P1 0.1039(13) 0.0735(11) 0.0720(11) 0.0165(10) 0.0059(10) 0.0115(10) P2 0.0909(12) 0.0763(11) 0.0777(11) 0.0231(9) 0.0318(9) 0.0086(9) F1 0.148(5) 0.157(5) 0.102(4) 0.008(4) -0.021(3) 0.045(4) F2 0.167(6) 0.237(8) 0.141(5) 0.066(5) 0.067(5) 0.020(6) F3 0.198(7) 0.126(5) 0.233(8) 0.023(5) -0.016(6) 0.070(5) F4 0.178(7) 0.283(10) 0.178(7) 0.115(7) 0.012(5) -0.088(7) F5 0.152(5) 0.154(5) 0.097(4) 0.030(4) -0.024(3) -0.015(4) F6 0.268(9) 0.160(6) 0.194(7) -0.011(5) 0.037(7) 0.125(6) F7 0.347(12) 0.184(7) 0.106(4) 0.035(5) -0.023(6) 0.107(7) F8 0.171(5) 0.099(3) 0.161(5) 0.057(3) 0.072(4) 0.018(3) F9 0.222(8) 0.186(7) 0.276(9) 0.069(6) 0.186(8) 0.062(6) F10 0.257(9) 0.255(10) 0.123(5) -0.033(6) -0.049(6) 0.124(8) F11 0.204(7) 0.206(7) 0.301(10) 0.134(7) 0.170(7) 0.114(6) F12 0.222(7) 0.090(4) 0.261(8) 0.055(4) 0.126(7) 0.010(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 Cu1 O1 1.964(3) . ? Cu1 N2 1.987(5) . ? Cu1 N1 1.996(5) . ? Cu1 N3 2.048(5) . ? Cu1 Cl1 2.4598(16) . ? Cu2 N5 1.989(5) . ? Cu2 O2 1.997(3) . ? Cu2 N4 1.998(5) . ? Cu2 N6 2.011(5) . ? Cu2 Cl1 2.4633(16) . ? O1 C1 1.366(6) . ? O2 C19 1.358(5) . ? N1 C14 1.341(7) . ? N1 C18 1.358(8) . ? N2 C12 1.491(10) . ? N2 C10 1.501(9) . ? N2 C9 1.509(10) . ? N3 C8 1.446(9) . ? N3 C7 1.476(9) . ? N4 C36 1.348(8) . ? N4 C32 1.354(7) . ? N5 C27 1.496(13) . ? N5 C30 1.500(11) . ? N5 C28 1.507(11) . ? N6 C26 1.476(9) . ? N6 C25 1.504(9) . ? C1 C2 1.372(9) . ? C1 C6 1.383(8) . ? C2 C3 1.379(10) . ? C3 C4 1.329(16) . ? C4 C5 1.360(16) . ? C5 C6 1.429(11) . ? C6 C7 1.477(11) . ? C8 C9 1.492(12) . ? C10 C11 1.547(12) . ? C11 C13 1.518(10) . ? C11 C12 1.530(12) . ? C11 C14 1.547(13) . ? C14 C15 1.368(13) . ? C15 C16 1.347(16) . ? C16 C17 1.397(16) . ? C17 C18 1.362(9) . ? C19 C20 1.375(7) . ? C19 C24 1.400(7) . ? C20 C21 1.382(9) . ? C21 C22 1.351(12) . ? C22 C23 1.341(13) . ? C23 C24 1.417(10) . ? C24 C25 1.458(9) . ? C26 C27 1.509(15) . ? C28 C29 1.555(13) . ? C29 C32 1.520(14) . ? C29 C31 1.531(10) . ? C29 C30 1.569(14) . ? C32 C33 1.417(15) . ? C33 C34 1.312(16) . ? C34 C35 1.341(14) . ? C35 C36 1.371(9) . ? P1 F6 1.505(7) . ? P1 F4 1.515(7) . ? P1 F2 1.541(6) . ? P1 F5 1.557(5) . ? P1 F1 1.564(5) . ? P1 F3 1.621(7) . ? P2 F10 1.500(7) . ? P2 F11 1.521(6) . ? P2 F9 1.534(7) . ? P2 F12 1.544(6) . ? P2 F7 1.560(7) . ? P2 F8 1.588(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N2 150.0(2) . . ? O1 Cu1 N1 92.64(17) . . ? N2 Cu1 N1 91.4(2) . . ? O1 Cu1 N3 89.85(19) . . ? N2 Cu1 N3 85.2(3) . . ? N1 Cu1 N3 176.4(2) . . ? O1 Cu1 Cl1 105.05(13) . . ? N2 Cu1 Cl1 104.38(16) . . ? N1 Cu1 Cl1 93.60(14) . . ? N3 Cu1 Cl1 88.30(15) . . ? N5 Cu2 O2 149.7(2) . . ? N5 Cu2 N4 91.0(3) . . ? O2 Cu2 N4 92.26(16) . . ? N5 Cu2 N6 85.3(3) . . ? O2 Cu2 N6 90.87(18) . . ? N4 Cu2 N6 176.3(2) . . ? N5 Cu2 Cl1 104.45(18) . . ? O2 Cu2 Cl1 105.56(11) . . ? N4 Cu2 Cl1 92.13(13) . . ? N6 Cu2 Cl1 88.86(15) . . ? Cu1 Cl1 Cu2 176.35(7) . . ? C1 O1 Cu1 115.4(3) . . ? C19 O2 Cu2 112.8(3) . . ? C14 N1 C18 119.6(6) . . ? C14 N1 Cu1 124.1(5) . . ? C18 N1 Cu1 116.2(4) . . ? C12 N2 C10 88.4(6) . . ? C12 N2 C9 119.9(6) . . ? C10 N2 C9 121.4(6) . . ? C12 N2 Cu1 113.5(4) . . ? C10 N2 Cu1 103.6(4) . . ? C9 N2 Cu1 108.2(5) . . ? C8 N3 C7 113.2(6) . . ? C8 N3 Cu1 107.4(5) . . ? C7 N3 Cu1 115.4(4) . . ? C36 N4 C32 118.6(6) . . ? C36 N4 Cu2 116.5(3) . . ? C32 N4 Cu2 124.8(6) . . ? C27 N5 C30 117.4(7) . . ? C27 N5 C28 123.2(7) . . ? C30 N5 C28 88.1(7) . . ? C27 N5 Cu2 108.9(6) . . ? C30 N5 Cu2 114.2(5) . . ? C28 N5 Cu2 103.3(4) . . ? C26 N6 C25 115.3(6) . . ? C26 N6 Cu2 107.4(6) . . ? C25 N6 Cu2 115.3(3) . . ? O1 C1 C2 121.2(5) . . ? O1 C1 C6 118.6(6) . . ? C2 C1 C6 120.2(6) . . ? C1 C2 C3 120.9(8) . . ? C4 C3 C2 120.8(10) . . ? C3 C4 C5 119.9(8) . . ? C4 C5 C6 121.8(8) . . ? C1 C6 C5 116.5(8) . . ? C1 C6 C7 118.8(6) . . ? C5 C6 C7 124.6(7) . . ? N3 C7 C6 111.7(5) . . ? N3 C8 C9 108.2(6) . . ? C8 C9 N2 109.4(6) . . ? N2 C10 C11 88.5(5) . . ? C13 C11 C12 115.9(7) . . ? C13 C11 C10 114.6(7) . . ? C12 C11 C10 85.4(7) . . ? C13 C11 C14 114.3(9) . . ? C12 C11 C14 109.3(5) . . ? C10 C11 C14 114.1(6) . . ? N2 C12 C11 89.5(5) . . ? N1 C14 C15 119.3(8) . . ? N1 C14 C11 116.8(7) . . ? C15 C14 C11 123.8(8) . . ? C16 C15 C14 121.0(9) . . ? C15 C16 C17 120.9(9) . . ? C18 C17 C16 115.8(9) . . ? N1 C18 C17 123.3(7) . . ? O2 C19 C20 121.9(4) . . ? O2 C19 C24 117.4(5) . . ? C20 C19 C24 120.6(5) . . ? C19 C20 C21 119.4(6) . . ? C22 C21 C20 121.7(8) . . ? C23 C22 C21 119.2(7) . . ? C22 C23 C24 122.7(7) . . ? C19 C24 C23 116.4(6) . . ? C19 C24 C25 120.2(5) . . ? C23 C24 C25 123.4(6) . . ? C24 C25 N6 110.0(4) . . ? N6 C26 C27 107.1(6) . . ? N5 C27 C26 107.5(6) . . ? N5 C28 C29 89.6(6) . . ? C32 C29 C31 114.2(11) . . ? C32 C29 C28 114.3(6) . . ? C31 C29 C28 114.7(8) . . ? C32 C29 C30 110.8(5) . . ? C31 C29 C30 115.4(9) . . ? C28 C29 C30 84.0(8) . . ? N5 C30 C29 89.3(6) . . ? N4 C32 C33 118.1(8) . . ? N4 C32 C29 116.2(8) . . ? C33 C32 C29 125.2(7) . . ? C34 C33 C32 121.2(8) . . ? C33 C34 C35 121.0(10) . . ? C34 C35 C36 118.3(10) . . ? N4 C36 C35 122.7(6) . . ? F6 P1 F4 96.5(7) . . ? F6 P1 F2 90.4(5) . . ? F4 P1 F2 173.1(6) . . ? F6 P1 F5 89.5(4) . . ? F4 P1 F5 89.4(4) . . ? F2 P1 F5 90.5(4) . . ? F6 P1 F1 90.9(4) . . ? F4 P1 F1 90.3(4) . . ? F2 P1 F1 89.7(4) . . ? F5 P1 F1 179.5(4) . . ? F6 P1 F3 175.4(6) . . ? F4 P1 F3 88.1(6) . . ? F2 P1 F3 85.0(5) . . ? F5 P1 F3 90.3(4) . . ? F1 P1 F3 89.3(4) . . ? F10 P2 F11 87.6(5) . . ? F10 P2 F9 93.1(5) . . ? F11 P2 F9 175.9(5) . . ? F10 P2 F12 95.1(5) . . ? F11 P2 F12 87.6(4) . . ? F9 P2 F12 96.4(4) . . ? F10 P2 F7 174.5(6) . . ? F11 P2 F7 89.4(6) . . ? F9 P2 F7 89.6(5) . . ? F12 P2 F7 89.4(5) . . ? F10 P2 F8 86.9(5) . . ? F11 P2 F8 90.4(4) . . ? F9 P2 F8 85.6(4) . . ? F12 P2 F8 177.1(4) . . ? F7 P2 F8 88.5(4) . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.087 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.088 # Attachment 'YK06-49.cif' data_yk0649 _database_code_depnum_ccdc_archive 'CCDC 678933' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H33 Cl Cu F6 N3 O1.50 P2' _chemical_formula_weight 734.52 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.345(3) _cell_length_b 16.135(3) _cell_length_c 17.130(3) _cell_angle_alpha 63.31(3) _cell_angle_beta 86.81(3) _cell_angle_gamma 76.71(3) _cell_volume 3202.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13558 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 30.42 _exptl_crystal_description irregular _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Synchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13558 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 30.42 _reflns_number_total 13558 _reflns_number_gt 10596 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1280P)^2^+0.6473P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0108(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13558 _refine_ls_number_parameters 805 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1770 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 -0.01484(3) 0.33343(3) 0.27989(2) 0.04118(13) Uani 1 1 d . . . Cu2 Cu 0.50751(3) 0.63535(3) 0.07440(2) 0.03992(13) Uani 1 1 d . . . Cl1 Cl 0.62371(7) 0.59732(7) -0.01673(6) 0.0583(2) Uani 1 1 d . . . Cl2 Cl -0.14448(8) 0.36890(9) 0.17267(7) 0.0709(3) Uani 1 1 d . . . N1 N -0.1209(2) 0.3309(2) 0.3719(2) 0.0509(7) Uani 1 1 d . . . N2 N 0.0201(2) 0.4456(2) 0.28731(19) 0.0464(6) Uani 1 1 d . . . N3 N 0.1040(2) 0.34630(18) 0.19771(17) 0.0402(6) Uani 1 1 d . . . H3' H 0.0758 0.3907 0.1438 0.048 Uiso 1 1 calc R . . N4 N 0.6084(2) 0.65526(19) 0.14940(17) 0.0432(6) Uani 1 1 d . . . N5 N 0.4506(2) 0.55629(18) 0.18707(16) 0.0395(6) Uani 1 1 d . . . N6 N 0.3832(2) 0.62239(18) 0.01750(16) 0.0392(6) Uani 1 1 d . . . H6' H 0.4077 0.5753 0.0012 0.047 Uiso 1 1 calc R . . P1 P 0.05402(7) 0.10862(5) 0.31010(5) 0.0413(2) Uani 1 1 d . . . P2 P 0.43071(6) 0.86314(5) -0.07527(5) 0.03859(19) Uani 1 1 d . . . P3 P 0.35581(8) 0.29745(7) 0.47968(6) 0.0534(2) Uani 1 1 d . . . P4 P 0.12470(9) 0.73524(8) 0.26687(8) 0.0638(3) Uani 1 1 d . . . O1 O 0.02759(19) 0.18790(15) 0.33648(14) 0.0462(5) Uani 1 1 d . . . O2 O 0.45305(19) 0.78504(15) 0.01648(14) 0.0449(5) Uani 1 1 d . . . C1 C -0.1766(4) 0.2652(3) 0.3912(3) 0.0658(11) Uani 1 1 d . . . H1 H -0.1594 0.2228 0.3670 0.079 Uiso 1 1 calc R . . C2 C -0.2583(4) 0.2577(4) 0.4454(3) 0.0738(12) Uani 1 1 d . . . H2 H -0.2961 0.2120 0.4570 0.089 Uiso 1 1 calc R . . C3 C -0.2819(4) 0.3203(4) 0.4816(3) 0.0817(14) Uani 1 1 d . . . H3 H -0.3358 0.3174 0.5189 0.098 Uiso 1 1 calc R . . C4 C -0.2249(4) 0.3866(4) 0.4620(3) 0.0733(12) Uani 1 1 d . . . H4 H -0.2398 0.4286 0.4867 0.088 Uiso 1 1 calc R . . C5 C -0.1453(3) 0.3925(3) 0.4059(2) 0.0512(8) Uani 1 1 d . . . C6 C -0.0815(3) 0.4671(3) 0.3804(2) 0.0499(8) Uani 1 1 d . . . C7 C -0.1102(4) 0.5315(4) 0.4256(3) 0.0743(13) Uani 1 1 d . . . H7A H -0.1069 0.4930 0.4878 0.111 Uiso 1 1 calc R . . H7B H -0.1789 0.5697 0.4062 0.111 Uiso 1 1 calc R . . H7C H -0.0628 0.5722 0.4111 0.111 Uiso 1 1 calc R . . C8 C -0.0747(3) 0.5188(2) 0.2797(2) 0.0547(9) Uani 1 1 d . . . H8A H -0.1319 0.5187 0.2472 0.066 Uiso 1 1 calc R . . H8B H -0.0633 0.5825 0.2581 0.066 Uiso 1 1 calc R . . C9 C 0.0339(3) 0.4229(3) 0.3819(3) 0.0550(9) Uani 1 1 d . . . H9A H 0.0790 0.4569 0.3920 0.066 Uiso 1 1 calc R . . H9B H 0.0536 0.3552 0.4209 0.066 Uiso 1 1 calc R . . C10 C 0.1030(4) 0.4770(3) 0.2286(3) 0.0647(11) Uani 1 1 d . . . H10A H 0.1423 0.5065 0.2506 0.078 Uiso 1 1 calc R . . H10B H 0.0737 0.5236 0.1706 0.078 Uiso 1 1 calc R . . C11 C 0.1721(3) 0.3916(3) 0.2243(3) 0.0535(9) Uani 1 1 d . . . H11A H 0.2237 0.4108 0.1817 0.064 Uiso 1 1 calc R . . H11B H 0.2069 0.3474 0.2809 0.064 Uiso 1 1 calc R . . C12 C 0.1661(3) 0.2651(2) 0.1848(2) 0.0438(7) Uani 1 1 d . . . H12A H 0.1960 0.2140 0.2408 0.053 Uiso 1 1 calc R . . H12B H 0.2221 0.2851 0.1477 0.053 Uiso 1 1 calc R . . C13 C 0.1015(3) 0.2286(2) 0.1434(2) 0.0416(7) Uani 1 1 d . . . C14 C 0.0924(3) 0.2695(3) 0.0527(2) 0.0538(9) Uani 1 1 d . . . H14 H 0.1257 0.3180 0.0196 0.065 Uiso 1 1 calc R . . C15 C 0.0342(4) 0.2388(3) 0.0107(2) 0.0642(11) Uani 1 1 d . . . H15 H 0.0271 0.2681 -0.0501 0.077 Uiso 1 1 calc R . . C16 C -0.0128(3) 0.1656(3) 0.0585(3) 0.0626(10) Uani 1 1 d . . . H16 H -0.0514 0.1448 0.0302 0.075 Uiso 1 1 calc R . . C17 C -0.0028(3) 0.1222(3) 0.1497(3) 0.0556(9) Uani 1 1 d . . . H17 H -0.0327 0.0710 0.1821 0.067 Uiso 1 1 calc R . . C18 C 0.0517(3) 0.1550(2) 0.1925(2) 0.0428(7) Uani 1 1 d . . . C19 C 0.1807(3) 0.0377(2) 0.3526(2) 0.0514(8) Uani 1 1 d . . . C20 C 0.2350(3) 0.0606(3) 0.4056(3) 0.0667(11) Uani 1 1 d . . . H20 H 0.2039 0.1087 0.4209 0.080 Uiso 1 1 calc R . . C21 C 0.3359(4) 0.0102(4) 0.4347(4) 0.0893(16) Uani 1 1 d . . . H21 H 0.3720 0.0246 0.4702 0.107 Uiso 1 1 calc R . . C22 C 0.3831(4) -0.0597(4) 0.4124(4) 0.0933(19) Uani 1 1 d . . . H22 H 0.4510 -0.0920 0.4319 0.112 Uiso 1 1 calc R . . C23 C 0.3305(5) -0.0824(4) 0.3613(3) 0.0922(19) Uani 1 1 d . . . H23 H 0.3631 -0.1307 0.3467 0.111 Uiso 1 1 calc R . . C24 C 0.2291(4) -0.0348(3) 0.3307(3) 0.0667(11) Uani 1 1 d . . . H24 H 0.1941 -0.0511 0.2961 0.080 Uiso 1 1 calc R . . C25 C -0.0375(3) 0.0346(2) 0.3474(2) 0.0490(8) Uani 1 1 d . . . C26 C -0.0091(4) -0.0630(3) 0.3992(3) 0.0683(11) Uani 1 1 d . . . H26 H 0.0596 -0.0930 0.4173 0.082 Uiso 1 1 calc R . . C27 C -0.0847(5) -0.1156(4) 0.4238(3) 0.0880(16) Uani 1 1 d . . . H27 H -0.0661 -0.1813 0.4574 0.106 Uiso 1 1 calc R . . C28 C -0.1864(5) -0.0708(4) 0.3989(3) 0.0853(16) Uani 1 1 d . . . H28 H -0.2366 -0.1062 0.4162 0.102 Uiso 1 1 calc R . . C29 C -0.2141(4) 0.0254(4) 0.3489(3) 0.0709(12) Uani 1 1 d . . . H29 H -0.2833 0.0553 0.3332 0.085 Uiso 1 1 calc R . . C30 C -0.1405(3) 0.0789(3) 0.3212(3) 0.0576(9) Uani 1 1 d . . . H30 H -0.1597 0.1442 0.2854 0.069 Uiso 1 1 calc R . . C31 C 0.6784(3) 0.7040(3) 0.1050(2) 0.0600(10) Uani 1 1 d . . . H31 H 0.6897 0.7120 0.0482 0.072 Uiso 1 1 calc R . . C32 C 0.7345(3) 0.7430(3) 0.1394(3) 0.0656(11) Uani 1 1 d . . . H32 H 0.7816 0.7775 0.1062 0.079 Uiso 1 1 calc R . . C33 C 0.7194(3) 0.7300(3) 0.2227(3) 0.0640(11) Uani 1 1 d . . . H33 H 0.7564 0.7553 0.2476 0.077 Uiso 1 1 calc R . . C34 C 0.6488(3) 0.6788(3) 0.2702(3) 0.0550(9) Uani 1 1 d . . . H34 H 0.6378 0.6696 0.3274 0.066 Uiso 1 1 calc R . . C35 C 0.5940(2) 0.6409(2) 0.2325(2) 0.0402(7) Uani 1 1 d . . . C36 C 0.5167(3) 0.5827(2) 0.2819(2) 0.0443(7) Uani 1 1 d . . . C37 C 0.5108(4) 0.5629(3) 0.3782(3) 0.0675(11) Uani 1 1 d . . . H37A H 0.5782 0.5332 0.4069 0.101 Uiso 1 1 calc R . . H37B H 0.4650 0.5213 0.4063 0.101 Uiso 1 1 calc R . . H37C H 0.4853 0.6218 0.3816 0.101 Uiso 1 1 calc R . . C38 C 0.5285(3) 0.4965(2) 0.2619(2) 0.0468(7) Uani 1 1 d . . . H38A H 0.5966 0.4765 0.2444 0.056 Uiso 1 1 calc R . . H38B H 0.5063 0.4426 0.3080 0.056 Uiso 1 1 calc R . . C39 C 0.4125(3) 0.6206(3) 0.2293(2) 0.0475(8) Uani 1 1 d . . . H39A H 0.3544 0.6053 0.2653 0.057 Uiso 1 1 calc R . . H39B H 0.3989 0.6879 0.1886 0.057 Uiso 1 1 calc R . . C40 C 0.3757(3) 0.5117(3) 0.1699(2) 0.0531(9) Uani 1 1 d . . . H40A H 0.3317 0.4908 0.2187 0.064 Uiso 1 1 calc R . . H40B H 0.4112 0.4568 0.1617 0.064 Uiso 1 1 calc R . . C41 C 0.3126(3) 0.5857(3) 0.0882(2) 0.0482(8) Uani 1 1 d . . . H41A H 0.2659 0.5578 0.0713 0.058 Uiso 1 1 calc R . . H41B H 0.2719 0.6375 0.0987 0.058 Uiso 1 1 calc R . . C42 C 0.3232(2) 0.7050(2) -0.0605(2) 0.0426(7) Uani 1 1 d . . . H42A H 0.2924 0.7554 -0.0444 0.051 Uiso 1 1 calc R . . H42B H 0.2675 0.6852 -0.0766 0.051 Uiso 1 1 calc R . . C43 C 0.3862(3) 0.7444(2) -0.1391(2) 0.0404(7) Uani 1 1 d . . . C44 C 0.3910(3) 0.7096(3) -0.2005(2) 0.0505(8) Uani 1 1 d . . . H44 H 0.3561 0.6628 -0.1918 0.061 Uiso 1 1 calc R . . C45 C 0.4472(3) 0.7435(3) -0.2745(2) 0.0586(10) Uani 1 1 d . . . H45 H 0.4505 0.7188 -0.3145 0.070 Uiso 1 1 calc R . . C46 C 0.4979(3) 0.8136(3) -0.2883(2) 0.0605(10) Uani 1 1 d . . . H46 H 0.5359 0.8361 -0.3377 0.073 Uiso 1 1 calc R . . C47 C 0.4927(3) 0.8513(3) -0.2290(2) 0.0521(8) Uani 1 1 d . . . H47 H 0.5262 0.8996 -0.2395 0.063 Uiso 1 1 calc R . . C48 C 0.4379(3) 0.8171(2) -0.1543(2) 0.0399(6) Uani 1 1 d . . . C49 C 0.3036(3) 0.9366(2) -0.0872(2) 0.0419(7) Uani 1 1 d . . . C50 C 0.2490(3) 0.9236(3) -0.0117(2) 0.0517(8) Uani 1 1 d . . . H50 H 0.2765 0.8748 0.0425 0.062 Uiso 1 1 calc R . . C51 C 0.1546(3) 0.9836(3) -0.0182(3) 0.0597(9) Uani 1 1 d . . . H51 H 0.1195 0.9764 0.0321 0.072 Uiso 1 1 calc R . . C52 C 0.1119(3) 1.0538(3) -0.0980(3) 0.0589(9) Uani 1 1 d . . . H52 H 0.0485 1.0944 -0.1015 0.071 Uiso 1 1 calc R . . C53 C 0.1624(3) 1.0646(3) -0.1728(3) 0.0567(9) Uani 1 1 d . . . H53 H 0.1317 1.1106 -0.2270 0.068 Uiso 1 1 calc R . . C54 C 0.2585(3) 1.0074(2) -0.1675(2) 0.0505(8) Uani 1 1 d . . . H54 H 0.2934 1.0162 -0.2182 0.061 Uiso 1 1 calc R . . C55 C 0.5196(3) 0.9400(2) -0.1050(2) 0.0440(7) Uani 1 1 d . . . C56 C 0.4873(3) 1.0355(3) -0.1245(3) 0.0613(10) Uani 1 1 d . . . H56 H 0.4179 1.0620 -0.1232 0.074 Uiso 1 1 calc R . . C57 C 0.5588(4) 1.0911(3) -0.1459(3) 0.0722(12) Uani 1 1 d . . . H57 H 0.5370 1.1553 -0.1595 0.087 Uiso 1 1 calc R . . C58 C 0.6619(3) 1.0525(3) -0.1474(3) 0.0621(10) Uani 1 1 d . . . H58 H 0.7094 1.0908 -0.1631 0.075 Uiso 1 1 calc R . . C59 C 0.6940(3) 0.9576(3) -0.1256(3) 0.0581(9) Uani 1 1 d . . . H59 H 0.7638 0.9310 -0.1252 0.070 Uiso 1 1 calc R . . C60 C 0.6238(3) 0.9015(3) -0.1043(2) 0.0529(8) Uani 1 1 d . . . H60 H 0.6464 0.8369 -0.0893 0.063 Uiso 1 1 calc R . . F1 F 0.4718(3) 0.2978(4) 0.4622(4) 0.172(2) Uani 1 1 d . . . F2 F 0.2432(3) 0.2971(3) 0.4934(5) 0.225(4) Uani 1 1 d . . . F3 F 0.3435(5) 0.3867(3) 0.4957(3) 0.1569(19) Uani 1 1 d . . . F4 F 0.3344(5) 0.3649(4) 0.3815(2) 0.165(2) Uani 1 1 d . . . F5 F 0.3770(5) 0.2039(3) 0.4718(4) 0.166(2) Uani 1 1 d . . . F6 F 0.3816(5) 0.2293(4) 0.5777(2) 0.172(2) Uani 1 1 d . . . F7 F 0.1729(4) 0.7467(5) 0.1790(3) 0.165(2) Uani 1 1 d . . . F8 F 0.0792(4) 0.7286(5) 0.3550(3) 0.179(2) Uani 1 1 d . . . F9 F 0.0887(3) 0.8470(2) 0.2292(3) 0.1341(16) Uani 1 1 d . . . F10 F 0.0179(3) 0.7325(2) 0.2331(3) 0.1172(13) Uani 1 1 d . . . F11 F 0.1603(3) 0.6258(2) 0.3071(4) 0.1504(19) Uani 1 1 d . . . F12 F 0.2320(3) 0.7374(3) 0.2999(3) 0.1070(11) Uani 1 1 d . . . O3 O 0.1208(5) 0.4922(3) 0.0177(3) 0.140(2) Uani 1 1 d . . . H3A H 0.1862 0.5097 0.0003 0.168 Uiso 1 1 calc R . . H3B H 0.0761 0.5230 0.0484 0.168 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 0.0433(3) 0.0441(2) 0.0451(2) -0.02491(17) 0.00935(16) -0.01770(17) Cu2 0.0386(3) 0.0492(2) 0.0361(2) -0.01966(17) 0.00414(15) -0.01709(16) Cl1 0.0471(6) 0.0772(6) 0.0648(5) -0.0471(5) 0.0112(4) -0.0100(4) Cl2 0.0543(6) 0.1028(8) 0.0526(5) -0.0257(5) -0.0048(4) -0.0303(5) N1 0.0495(19) 0.0579(17) 0.0524(16) -0.0302(14) 0.0129(13) -0.0165(13) N2 0.0493(18) 0.0463(14) 0.0530(16) -0.0283(13) 0.0064(12) -0.0162(12) N3 0.0427(16) 0.0411(13) 0.0420(13) -0.0195(11) 0.0064(11) -0.0182(11) N4 0.0433(16) 0.0459(14) 0.0409(13) -0.0164(11) -0.0027(11) -0.0165(11) N5 0.0471(16) 0.0398(13) 0.0380(12) -0.0189(10) 0.0060(10) -0.0192(11) N6 0.0420(16) 0.0438(13) 0.0411(13) -0.0248(11) 0.0050(10) -0.0154(11) P1 0.0476(5) 0.0353(4) 0.0386(4) -0.0137(3) 0.0047(3) -0.0116(3) P2 0.0398(5) 0.0376(4) 0.0439(4) -0.0242(3) -0.0010(3) -0.0056(3) P3 0.0529(6) 0.0581(5) 0.0518(5) -0.0266(4) 0.0074(4) -0.0142(4) P4 0.0545(7) 0.0540(6) 0.0791(7) -0.0304(5) 0.0026(5) -0.0041(4) O1 0.0594(16) 0.0393(11) 0.0388(11) -0.0165(9) 0.0056(10) -0.0120(10) O2 0.0548(15) 0.0389(11) 0.0434(12) -0.0229(9) -0.0058(10) -0.0037(9) C1 0.069(3) 0.073(3) 0.070(3) -0.038(2) 0.028(2) -0.035(2) C2 0.075(3) 0.088(3) 0.068(3) -0.036(2) 0.029(2) -0.040(3) C3 0.063(3) 0.116(4) 0.077(3) -0.053(3) 0.031(2) -0.027(3) C4 0.060(3) 0.098(3) 0.076(3) -0.055(3) 0.022(2) -0.014(2) C5 0.045(2) 0.061(2) 0.0465(18) -0.0276(16) -0.0033(14) -0.0033(15) C6 0.046(2) 0.058(2) 0.0540(19) -0.0358(17) -0.0036(15) -0.0019(15) C7 0.070(3) 0.088(3) 0.087(3) -0.065(3) -0.001(2) -0.002(2) C8 0.064(2) 0.0432(17) 0.059(2) -0.0267(16) -0.0074(17) -0.0056(15) C9 0.054(2) 0.061(2) 0.062(2) -0.0396(18) -0.0094(17) -0.0077(16) C10 0.077(3) 0.060(2) 0.082(3) -0.044(2) 0.030(2) -0.042(2) C11 0.052(2) 0.065(2) 0.063(2) -0.0387(19) 0.0122(16) -0.0310(17) C12 0.044(2) 0.0485(17) 0.0444(16) -0.0229(14) 0.0115(13) -0.0189(14) C13 0.0440(19) 0.0421(15) 0.0459(16) -0.0258(13) 0.0094(13) -0.0119(13) C14 0.073(3) 0.0513(19) 0.0401(17) -0.0202(15) 0.0136(16) -0.0224(17) C15 0.087(3) 0.072(3) 0.0404(18) -0.0302(18) 0.0016(18) -0.018(2) C16 0.071(3) 0.081(3) 0.056(2) -0.045(2) 0.0057(18) -0.026(2) C17 0.067(3) 0.058(2) 0.057(2) -0.0337(17) 0.0103(17) -0.0269(18) C18 0.049(2) 0.0419(15) 0.0413(16) -0.0209(13) 0.0068(13) -0.0131(13) C19 0.053(2) 0.0447(17) 0.0459(18) -0.0122(14) 0.0051(15) -0.0095(15) C20 0.059(3) 0.065(2) 0.064(2) -0.020(2) -0.0067(19) -0.0098(19) C21 0.066(3) 0.091(4) 0.081(3) -0.008(3) -0.018(3) -0.021(3) C22 0.049(3) 0.096(4) 0.076(3) 0.003(3) 0.005(2) 0.002(3) C23 0.088(4) 0.070(3) 0.069(3) -0.008(2) 0.022(3) 0.020(3) C24 0.073(3) 0.054(2) 0.053(2) -0.0153(17) 0.0131(19) 0.0016(19) C25 0.059(2) 0.0454(17) 0.0443(17) -0.0193(14) 0.0125(15) -0.0192(15) C26 0.069(3) 0.050(2) 0.065(2) -0.0058(18) 0.009(2) -0.0203(18) C27 0.109(5) 0.062(3) 0.076(3) -0.005(2) 0.014(3) -0.045(3) C28 0.102(4) 0.094(4) 0.072(3) -0.029(3) 0.024(3) -0.068(3) C29 0.064(3) 0.098(3) 0.071(3) -0.048(3) 0.014(2) -0.038(2) C30 0.065(3) 0.059(2) 0.057(2) -0.0291(18) 0.0057(17) -0.0226(18) C31 0.052(2) 0.078(3) 0.0488(19) -0.0187(18) 0.0025(16) -0.0340(19) C32 0.056(3) 0.067(2) 0.067(2) -0.016(2) -0.0035(19) -0.0313(19) C33 0.064(3) 0.056(2) 0.080(3) -0.033(2) -0.015(2) -0.0198(18) C34 0.064(3) 0.0532(19) 0.056(2) -0.0312(17) -0.0073(17) -0.0131(17) C35 0.0408(18) 0.0361(14) 0.0431(15) -0.0189(12) -0.0045(12) -0.0041(12) C36 0.055(2) 0.0461(16) 0.0380(15) -0.0228(13) 0.0044(13) -0.0149(14) C37 0.084(3) 0.085(3) 0.045(2) -0.034(2) 0.0144(19) -0.032(2) C38 0.057(2) 0.0371(15) 0.0418(16) -0.0115(13) -0.0010(14) -0.0149(14) C39 0.045(2) 0.0590(19) 0.0507(18) -0.0344(16) 0.0118(14) -0.0162(15) C40 0.064(2) 0.055(2) 0.0484(18) -0.0210(16) 0.0067(16) -0.0343(17) C41 0.049(2) 0.0561(19) 0.0509(18) -0.0269(16) 0.0085(14) -0.0276(15) C42 0.0377(18) 0.0521(17) 0.0456(16) -0.0280(14) -0.0019(13) -0.0107(13) C43 0.0424(19) 0.0434(15) 0.0405(15) -0.0231(13) -0.0022(12) -0.0089(12) C44 0.064(2) 0.0507(18) 0.0495(18) -0.0315(15) 0.0005(15) -0.0164(16) C45 0.081(3) 0.061(2) 0.0471(19) -0.0365(17) 0.0074(17) -0.0158(19) C46 0.077(3) 0.066(2) 0.0443(18) -0.0297(17) 0.0173(17) -0.021(2) C47 0.061(2) 0.0524(19) 0.0507(19) -0.0270(16) 0.0124(16) -0.0203(16) C48 0.0431(19) 0.0393(15) 0.0411(15) -0.0226(13) 0.0018(12) -0.0064(12) C49 0.0417(19) 0.0435(16) 0.0476(16) -0.0266(14) -0.0017(13) -0.0093(13) C50 0.053(2) 0.0524(19) 0.0521(19) -0.0272(16) 0.0017(15) -0.0083(15) C51 0.052(2) 0.070(2) 0.068(2) -0.042(2) 0.0144(18) -0.0119(18) C52 0.036(2) 0.060(2) 0.085(3) -0.041(2) -0.0005(18) -0.0017(15) C53 0.049(2) 0.054(2) 0.064(2) -0.0248(18) -0.0101(17) -0.0070(16) C54 0.049(2) 0.0515(19) 0.0506(19) -0.0237(16) -0.0033(15) -0.0080(15) C55 0.045(2) 0.0432(16) 0.0521(18) -0.0283(14) -0.0009(14) -0.0088(13) C56 0.046(2) 0.051(2) 0.102(3) -0.048(2) -0.0031(19) -0.0079(15) C57 0.072(3) 0.054(2) 0.109(4) -0.049(2) 0.003(2) -0.0203(19) C58 0.060(3) 0.070(2) 0.075(3) -0.042(2) 0.0077(19) -0.029(2) C59 0.044(2) 0.067(2) 0.068(2) -0.035(2) 0.0081(16) -0.0131(17) C60 0.048(2) 0.0477(18) 0.058(2) -0.0226(16) 0.0036(15) -0.0059(14) F1 0.071(3) 0.167(4) 0.231(6) -0.046(4) 0.041(3) -0.041(3) F2 0.046(3) 0.130(4) 0.361(8) 0.008(4) 0.015(3) -0.018(2) F3 0.231(6) 0.127(3) 0.162(4) -0.102(3) 0.050(4) -0.063(4) F4 0.219(5) 0.176(4) 0.066(2) 0.002(2) -0.031(3) -0.093(4) F5 0.231(6) 0.113(3) 0.209(5) -0.113(4) 0.044(4) -0.062(3) F6 0.206(5) 0.178(5) 0.063(2) -0.011(2) -0.001(3) -0.006(4) F7 0.148(4) 0.263(6) 0.094(3) -0.094(4) 0.014(3) -0.038(4) F8 0.156(5) 0.247(6) 0.137(4) -0.106(4) 0.059(3) -0.024(4) F9 0.117(3) 0.0651(18) 0.203(4) -0.048(2) -0.062(3) 0.0006(18) F10 0.074(2) 0.087(2) 0.184(4) -0.052(2) -0.026(2) -0.0156(16) F11 0.128(3) 0.0590(18) 0.242(5) -0.052(3) -0.045(3) -0.0015(19) F12 0.076(2) 0.108(2) 0.142(3) -0.064(2) -0.0265(19) -0.0057(17) O3 0.223(6) 0.113(3) 0.071(2) -0.007(2) -0.011(3) -0.081(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 Cu1 N2 2.028(3) . ? Cu1 O1 2.044(2) . ? Cu1 N3 2.045(3) . ? Cu1 N1 2.052(3) . ? Cu1 Cl2 2.3766(13) . ? Cu2 N5 2.000(3) . ? Cu2 N6 2.066(3) . ? Cu2 N4 2.080(3) . ? Cu2 O2 2.113(2) . ? Cu2 Cl1 2.3177(12) . ? N1 C5 1.336(4) . ? N1 C1 1.344(5) . ? N2 C10 1.472(5) . ? N2 C8 1.485(5) . ? N2 C9 1.504(4) . ? N3 C12 1.481(4) . ? N3 C11 1.488(4) . ? N4 C31 1.339(4) . ? N4 C35 1.346(4) . ? N5 C40 1.468(4) . ? N5 C38 1.493(4) . ? N5 C39 1.499(4) . ? N6 C41 1.480(4) . ? N6 C42 1.493(4) . ? P1 O1 1.503(2) . ? P1 C19 1.788(4) . ? P1 C25 1.797(4) . ? P1 C18 1.805(3) . ? P2 O2 1.499(2) . ? P2 C49 1.794(3) . ? P2 C55 1.801(3) . ? P2 C48 1.803(3) . ? P3 F2 1.509(4) . ? P3 F4 1.536(4) . ? P3 F5 1.536(4) . ? P3 F6 1.542(4) . ? P3 F3 1.555(4) . ? P3 F1 1.561(4) . ? P4 F11 1.542(3) . ? P4 F7 1.553(4) . ? P4 F8 1.562(4) . ? P4 F9 1.578(3) . ? P4 F12 1.581(3) . ? P4 F10 1.585(3) . ? C1 C2 1.383(6) . ? C2 C3 1.378(7) . ? C3 C4 1.364(7) . ? C4 C5 1.381(6) . ? C5 C6 1.524(5) . ? C6 C7 1.526(5) . ? C6 C9 1.537(5) . ? C6 C8 1.551(5) . ? C10 C11 1.502(6) . ? C12 C13 1.506(4) . ? C13 C14 1.389(5) . ? C13 C18 1.401(4) . ? C14 C15 1.387(5) . ? C15 C16 1.369(6) . ? C16 C17 1.396(5) . ? C17 C18 1.390(5) . ? C19 C24 1.395(5) . ? C19 C20 1.409(6) . ? C20 C21 1.389(7) . ? C21 C22 1.360(9) . ? C22 C23 1.367(9) . ? C23 C24 1.391(7) . ? C25 C26 1.384(5) . ? C25 C30 1.389(6) . ? C26 C27 1.392(6) . ? C27 C28 1.372(8) . ? C28 C29 1.362(7) . ? C29 C30 1.381(6) . ? C31 C32 1.380(5) . ? C32 C33 1.356(6) . ? C33 C34 1.378(6) . ? C34 C35 1.393(4) . ? C35 C36 1.514(5) . ? C36 C37 1.535(5) . ? C36 C39 1.541(5) . ? C36 C38 1.549(4) . ? C40 C41 1.504(5) . ? C42 C43 1.509(5) . ? C43 C44 1.390(4) . ? C43 C48 1.413(4) . ? C44 C45 1.389(5) . ? C45 C46 1.373(6) . ? C46 C47 1.390(5) . ? C47 C48 1.388(5) . ? C49 C54 1.387(5) . ? C49 C50 1.403(5) . ? C50 C51 1.376(5) . ? C51 C52 1.369(6) . ? C52 C53 1.372(6) . ? C53 C54 1.378(5) . ? C55 C60 1.385(5) . ? C55 C56 1.385(5) . ? C56 C57 1.381(5) . ? C57 C58 1.378(6) . ? C58 C59 1.368(6) . ? C59 C60 1.374(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 O1 140.44(11) . . ? N2 Cu1 N3 83.61(11) . . ? O1 Cu1 N3 92.29(10) . . ? N2 Cu1 N1 87.48(12) . . ? O1 Cu1 N1 91.73(11) . . ? N3 Cu1 N1 170.03(11) . . ? N2 Cu1 Cl2 116.95(10) . . ? O1 Cu1 Cl2 102.60(8) . . ? N3 Cu1 Cl2 95.59(8) . . ? N1 Cu1 Cl2 92.43(10) . . ? N5 Cu2 N6 84.32(11) . . ? N5 Cu2 N4 86.84(11) . . ? N6 Cu2 N4 167.29(11) . . ? N5 Cu2 O2 118.64(10) . . ? N6 Cu2 O2 90.68(10) . . ? N4 Cu2 O2 85.55(10) . . ? N5 Cu2 Cl1 132.99(9) . . ? N6 Cu2 Cl1 93.45(8) . . ? N4 Cu2 Cl1 99.27(9) . . ? O2 Cu2 Cl1 108.32(8) . . ? C5 N1 C1 119.0(3) . . ? C5 N1 Cu1 126.7(3) . . ? C1 N1 Cu1 114.0(2) . . ? C10 N2 C8 117.7(3) . . ? C10 N2 C9 118.6(3) . . ? C8 N2 C9 88.8(3) . . ? C10 N2 Cu1 109.8(2) . . ? C8 N2 Cu1 111.0(2) . . ? C9 N2 Cu1 109.3(2) . . ? C12 N3 C11 110.5(3) . . ? C12 N3 Cu1 122.76(19) . . ? C11 N3 Cu1 105.5(2) . . ? C31 N4 C35 118.7(3) . . ? C31 N4 Cu2 115.5(2) . . ? C35 N4 Cu2 124.2(2) . . ? C40 N5 C38 118.5(3) . . ? C40 N5 C39 117.3(3) . . ? C38 N5 C39 88.8(2) . . ? C40 N5 Cu2 109.5(2) . . ? C38 N5 Cu2 115.1(2) . . ? C39 N5 Cu2 105.99(19) . . ? C41 N6 C42 109.4(3) . . ? C41 N6 Cu2 106.36(18) . . ? C42 N6 Cu2 121.05(19) . . ? O1 P1 C19 110.19(16) . . ? O1 P1 C25 111.52(15) . . ? C19 P1 C25 109.74(17) . . ? O1 P1 C18 111.12(14) . . ? C19 P1 C18 107.79(17) . . ? C25 P1 C18 106.36(16) . . ? O2 P2 C49 110.62(15) . . ? O2 P2 C55 111.92(15) . . ? C49 P2 C55 107.09(15) . . ? O2 P2 C48 112.01(13) . . ? C49 P2 C48 107.58(15) . . ? C55 P2 C48 107.38(15) . . ? F2 P3 F4 92.3(3) . . ? F2 P3 F5 91.8(3) . . ? F4 P3 F5 96.8(3) . . ? F2 P3 F6 89.8(3) . . ? F4 P3 F6 177.9(3) . . ? F5 P3 F6 82.9(3) . . ? F2 P3 F3 91.6(3) . . ? F4 P3 F3 88.2(3) . . ? F5 P3 F3 173.8(3) . . ? F6 P3 F3 92.0(3) . . ? F2 P3 F1 177.9(4) . . ? F4 P3 F1 86.1(3) . . ? F5 P3 F1 87.1(3) . . ? F6 P3 F1 91.8(3) . . ? F3 P3 F1 89.6(3) . . ? F11 P4 F7 91.5(3) . . ? F11 P4 F8 90.9(3) . . ? F7 P4 F8 176.5(4) . . ? F11 P4 F9 177.9(3) . . ? F7 P4 F9 90.3(3) . . ? F8 P4 F9 87.2(3) . . ? F11 P4 F12 88.5(2) . . ? F7 P4 F12 88.4(3) . . ? F8 P4 F12 89.1(3) . . ? F9 P4 F12 90.45(19) . . ? F11 P4 F10 91.1(2) . . ? F7 P4 F10 91.0(3) . . ? F8 P4 F10 91.5(3) . . ? F9 P4 F10 89.93(19) . . ? F12 P4 F10 179.3(2) . . ? P1 O1 Cu1 139.40(14) . . ? P2 O2 Cu2 135.43(13) . . ? N1 C1 C2 123.0(4) . . ? C3 C2 C1 117.7(4) . . ? C4 C3 C2 119.0(4) . . ? C3 C4 C5 121.1(4) . . ? N1 C5 C4 120.2(4) . . ? N1 C5 C6 117.0(3) . . ? C4 C5 C6 122.8(3) . . ? C5 C6 C7 113.9(3) . . ? C5 C6 C9 111.2(3) . . ? C7 C6 C9 116.6(3) . . ? C5 C6 C8 110.9(3) . . ? C7 C6 C8 115.8(3) . . ? C9 C6 C8 85.2(3) . . ? N2 C8 C6 89.2(3) . . ? N2 C9 C6 89.0(3) . . ? N2 C10 C11 108.5(3) . . ? N3 C11 C10 106.2(3) . . ? N3 C12 C13 111.4(3) . . ? C14 C13 C18 119.2(3) . . ? C14 C13 C12 118.1(3) . . ? C18 C13 C12 122.7(3) . . ? C15 C14 C13 120.8(3) . . ? C16 C15 C14 120.2(3) . . ? C15 C16 C17 119.9(3) . . ? C18 C17 C16 120.4(3) . . ? C17 C18 C13 119.5(3) . . ? C17 C18 P1 121.1(3) . . ? C13 C18 P1 119.4(2) . . ? C24 C19 C20 119.5(4) . . ? C24 C19 P1 122.3(3) . . ? C20 C19 P1 118.1(3) . . ? C21 C20 C19 118.9(5) . . ? C22 C21 C20 121.3(6) . . ? C21 C22 C23 119.9(5) . . ? C22 C23 C24 121.3(5) . . ? C23 C24 C19 119.1(5) . . ? C26 C25 C30 120.0(4) . . ? C26 C25 P1 122.8(3) . . ? C30 C25 P1 117.2(3) . . ? C25 C26 C27 119.2(5) . . ? C28 C27 C26 120.3(4) . . ? C29 C28 C27 120.2(4) . . ? C28 C29 C30 120.7(5) . . ? C29 C30 C25 119.5(4) . . ? N4 C31 C32 123.1(4) . . ? C33 C32 C31 118.5(4) . . ? C32 C33 C34 119.4(3) . . ? C33 C34 C35 119.9(4) . . ? N4 C35 C34 120.3(3) . . ? N4 C35 C36 117.4(3) . . ? C34 C35 C36 122.3(3) . . ? C35 C36 C37 114.3(3) . . ? C35 C36 C39 111.4(3) . . ? C37 C36 C39 115.6(3) . . ? C35 C36 C38 109.8(3) . . ? C37 C36 C38 117.2(3) . . ? C39 C36 C38 85.3(2) . . ? N5 C38 C36 89.0(2) . . ? N5 C39 C36 89.2(2) . . ? N5 C40 C41 107.0(3) . . ? N6 C41 C40 108.7(3) . . ? N6 C42 C43 114.2(3) . . ? C44 C43 C48 118.7(3) . . ? C44 C43 C42 118.4(3) . . ? C48 C43 C42 122.9(3) . . ? C45 C44 C43 121.1(3) . . ? C46 C45 C44 119.7(3) . . ? C45 C46 C47 120.4(3) . . ? C48 C47 C46 120.3(3) . . ? C47 C48 C43 119.7(3) . . ? C47 C48 P2 121.6(2) . . ? C43 C48 P2 118.7(2) . . ? C54 C49 C50 118.8(3) . . ? C54 C49 P2 122.8(3) . . ? C50 C49 P2 118.5(3) . . ? C51 C50 C49 119.7(4) . . ? C52 C51 C50 120.6(4) . . ? C51 C52 C53 120.3(4) . . ? C52 C53 C54 120.0(4) . . ? C53 C54 C49 120.5(3) . . ? C60 C55 C56 119.0(3) . . ? C60 C55 P2 119.0(2) . . ? C56 C55 P2 121.9(3) . . ? C57 C56 C55 119.6(4) . . ? C58 C57 C56 120.8(4) . . ? C59 C58 C57 119.4(4) . . ? C58 C59 C60 120.4(4) . . ? C59 C60 C55 120.7(3) . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.922 _refine_diff_density_min -0.671 _refine_diff_density_rms 0.092