# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_zzzbs _database_code_depnum_ccdc_archive 'CCDC 910210' #TrackingRef 'web_deposit_cif_file_0_GalinaRomanenko_1355844366.all(295-150-103)_last (1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H18 Cu2 F12 N12' _chemical_formula_weight 937.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1229(4) _cell_length_b 13.8932(6) _cell_length_c 14.3935(7) _cell_angle_alpha 76.435(3) _cell_angle_beta 73.076(3) _cell_angle_gamma 87.607(3) _cell_volume 1695.94(13) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 3531 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 22.57 _exptl_crystal_description box _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.836 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3511 _exptl_absorpt_correction_T_max 0.4061 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21154 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.1253 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.25 _reflns_number_total 6094 _reflns_number_gt 3631 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6094 _refine_ls_number_parameters 588 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.938 _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 0.04557(7) 0.20394(4) 0.53060(5) 0.01904(19) Uani 1 1 d . . . Cu2 Cu -0.04817(7) 0.31423(4) 0.30429(5) 0.0216(2) Uani 1 1 d . . . N1AA N 0.0260(5) 0.2433(3) 0.1125(3) 0.0235(11) Uani 1 1 d . . . N1A N -0.0333(5) 0.3089(3) 0.1676(3) 0.0222(11) Uani 1 1 d . . . N8A N -0.1739(5) 0.4290(3) 0.2672(3) 0.0173(10) Uani 1 1 d . A . N14A N -0.1159(5) 0.3646(3) 0.4318(3) 0.0191(10) Uani 1 1 d . . . N15A N -0.0884(5) 0.3362(3) 0.5217(3) 0.0204(11) Uani 1 1 d . . . N1B N 0.1759(5) 0.2985(3) 0.3091(3) 0.0182(10) Uani 1 1 d . . . N6B N 0.1927(5) 0.2651(3) 0.4007(3) 0.0176(10) Uani 1 1 d . . . N8B N 0.2486(5) 0.2116(3) 0.5738(3) 0.0174(10) Uani 1 1 d . . . N1C N -0.1181(4) 0.1647(3) 0.3822(3) 0.0194(10) Uani 1 1 d . . . N6C N -0.0841(4) 0.1412(3) 0.4702(3) 0.0168(10) Uani 1 1 d . . . N8C N -0.0838(4) 0.1050(3) 0.6546(3) 0.0179(10) Uani 1 1 d . . . F1A F 0.0275(19) 0.2651(8) -0.1395(6) 0.041(4) Uani 0.51(3) 1 d PDU A 3 F2A F 0.1857(10) 0.1928(13) -0.0639(11) 0.049(4) Uani 0.51(3) 1 d PDU A 3 F3A F -0.037(2) 0.1273(8) -0.0255(15) 0.052(5) Uani 0.51(3) 1 d PDU A 3 F1AA F 0.1804(13) 0.2194(14) -0.0996(16) 0.078(5) Uani 0.49(3) 1 d PDU A 4 F2AA F -0.053(3) 0.2421(14) -0.1135(15) 0.084(5) Uani 0.49(3) 1 d PDU A 4 F3AA F -0.004(2) 0.1184(7) -0.0100(14) 0.034(4) Uani 0.49(3) 1 d PDU A 4 F1B F 0.4825(4) 0.4269(2) 0.1030(2) 0.0438(9) Uani 1 1 d U . . F2B F 0.3526(4) 0.3097(2) 0.0876(2) 0.0363(9) Uani 1 1 d U . . F3B F 0.2410(4) 0.4419(2) 0.1194(2) 0.0347(8) Uani 1 1 d U . . F1C F -0.3115(3) 0.1865(2) 0.2574(2) 0.0310(8) Uani 1 1 d U . . F2C F -0.1993(3) 0.0511(2) 0.2339(2) 0.0310(8) Uani 1 1 d U . . F3C F -0.4212(3) 0.0454(2) 0.3389(2) 0.0330(8) Uani 1 1 d U . . F11 F -0.276(2) 0.3311(17) 0.7452(11) 0.032(4) Uani 0.55(7) 1 d PDU B 1 F12 F -0.0310(16) 0.3446(18) 0.6936(12) 0.026(3) Uani 0.55(7) 1 d PDU B 1 F13 F -0.162(3) 0.4758(8) 0.7044(13) 0.037(4) Uani 0.55(7) 1 d PDU B 1 F11A F -0.212(5) 0.4675(16) 0.7158(17) 0.052(5) Uani 0.45(7) 1 d PDU B 2 F12A F -0.0204(15) 0.369(3) 0.6909(16) 0.040(5) Uani 0.45(7) 1 d PDU B 2 F13A F -0.250(3) 0.311(2) 0.7400(15) 0.035(5) Uani 0.45(7) 1 d PDU B 2 C3A C -0.0139(6) 0.2743(4) 0.0280(4) 0.0256(14) Uani 1 1 d D A . C4A C 0.0342(7) 0.2149(4) -0.0505(4) 0.0391(15) Uani 1 1 d DU . . C5A C -0.0994(6) 0.3593(4) 0.0265(4) 0.0239(13) Uani 1 1 d . . . H5AA H -0.1395 0.3946 -0.0235 0.029 Uiso 1 1 calc R A . C6A C -0.1098(6) 0.3781(4) 0.1186(4) 0.0203(13) Uani 1 1 d . A . C7A C -0.1874(6) 0.4505(4) 0.1744(4) 0.0190(12) Uani 1 1 d . . . C10A C -0.3278(6) 0.5631(4) 0.3086(4) 0.0247(14) Uani 1 1 d . A . H10A H -0.3777 0.5992 0.3550 0.030 Uiso 1 1 calc R . . C11A C -0.3406(6) 0.5874(4) 0.2129(4) 0.0270(14) Uani 1 1 d . . . H11A H -0.3981 0.6415 0.1942 0.032 Uiso 1 1 calc R A . C12A C -0.2692(6) 0.5327(4) 0.1439(4) 0.0252(14) Uani 1 1 d . A . H12A H -0.2759 0.5504 0.0788 0.030 Uiso 1 1 calc R . . C9A C -0.2389(6) 0.4838(4) 0.3343(4) 0.0203(13) Uani 1 1 d . . . C13A C -0.2043(6) 0.4457(4) 0.4285(4) 0.0195(13) Uani 1 1 d . A . C16A C -0.1631(6) 0.4033(3) 0.5741(3) 0.0194(13) Uani 1 1 d D A . C17A C -0.1586(6) 0.3884(3) 0.6799(4) 0.0277(13) Uani 1 1 d DU . . C21A C -0.2360(6) 0.4731(4) 0.5188(4) 0.0221(13) Uani 1 1 d . . . H21A H -0.2929 0.5260 0.5377 0.027 Uiso 1 1 calc R A . C1B C 0.3170(6) 0.3342(3) 0.2499(4) 0.0184(13) Uani 1 1 d . . . C3B C 0.3462(7) 0.3782(4) 0.1410(4) 0.0284(14) Uani 1 1 d U . . C4B C 0.4218(6) 0.3241(3) 0.3029(4) 0.0201(13) Uani 1 1 d . . . H4BA H 0.5251 0.3430 0.2794 0.024 Uiso 1 1 calc R . . C5B C 0.3381(6) 0.2790(3) 0.3996(4) 0.0172(12) Uani 1 1 d . . . C7B C 0.3719(6) 0.2474(3) 0.4946(4) 0.0179(13) Uani 1 1 d . . . C9B C 0.2738(6) 0.1820(4) 0.6630(4) 0.0235(13) Uani 1 1 d . . . H9BA H 0.1904 0.1577 0.7180 0.028 Uiso 1 1 calc R . . C10B C 0.4153(6) 0.1851(4) 0.6788(4) 0.0227(13) Uani 1 1 d . . . H10B H 0.4261 0.1639 0.7427 0.027 Uiso 1 1 calc R . . C11B C 0.5399(6) 0.2200(4) 0.5985(4) 0.0249(14) Uani 1 1 d . . . H11B H 0.6372 0.2222 0.6063 0.030 Uiso 1 1 calc R . . C12B C 0.5165(6) 0.2516(4) 0.5058(4) 0.0224(13) Uani 1 1 d . . . H12B H 0.5990 0.2761 0.4503 0.027 Uiso 1 1 calc R . . C2C C -0.2193(6) 0.0928(4) 0.3873(4) 0.0199(13) Uani 1 1 d . . . C3C C -0.2858(6) 0.0947(4) 0.3047(4) 0.0224(13) Uani 1 1 d U . . C4C C -0.2505(6) 0.0242(4) 0.4784(4) 0.0188(13) Uani 1 1 d . . . H4CA H -0.3148 -0.0318 0.5003 0.023 Uiso 1 1 calc R . . C5C C -0.1632(6) 0.0587(3) 0.5292(4) 0.0174(12) Uani 1 1 d . . . C7C C -0.1551(6) 0.0338(4) 0.6308(4) 0.0192(13) Uani 1 1 d . . . C9C C -0.0904(6) 0.0941(4) 0.7513(4) 0.0219(13) Uani 1 1 d . . . H9CA H -0.0505 0.1453 0.7691 0.026 Uiso 1 1 calc R . . C10C C -0.1523(6) 0.0122(4) 0.8249(4) 0.0252(14) Uani 1 1 d . . . H10C H -0.1533 0.0073 0.8906 0.030 Uiso 1 1 calc R . . C11C C -0.2132(6) -0.0629(4) 0.7983(4) 0.0275(14) Uani 1 1 d . . . H11C H -0.2498 -0.1216 0.8452 0.033 Uiso 1 1 calc R . . C12C C -0.2193(6) -0.0506(4) 0.7020(4) 0.0219(13) Uani 1 1 d . . . H12C H -0.2666 -0.0990 0.6847 0.026 Uiso 1 1 calc R . . N1S N -0.4998(9) 0.1313(7) -0.0857(7) 0.120(3) Uani 1 1 d . . . C1S C -0.4508(10) 0.1248(8) -0.0196(7) 0.096(3) Uani 1 1 d . . . C2S C -0.3945(9) 0.1146(9) 0.0641(7) 0.128(4) Uani 1 1 d . . . H2SA H -0.3427 0.1750 0.0594 0.192 Uiso 1 1 calc R . . H2SB H -0.3242 0.0612 0.0653 0.192 Uiso 1 1 calc R . . H2SC H -0.4785 0.1005 0.1242 0.192 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 0.0193(4) 0.0192(4) 0.0192(4) -0.0042(3) -0.0064(3) -0.0010(3) Cu2 0.0256(4) 0.0219(4) 0.0203(4) -0.0073(3) -0.0104(3) 0.0066(3) N1AA 0.028(3) 0.024(3) 0.020(3) -0.006(2) -0.009(2) 0.002(2) N1A 0.026(3) 0.022(3) 0.021(3) -0.009(2) -0.008(2) 0.006(2) N8A 0.022(3) 0.013(2) 0.016(3) 0.001(2) -0.010(2) -0.0010(19) N14A 0.019(3) 0.017(2) 0.023(3) -0.002(2) -0.010(2) 0.003(2) N15A 0.022(3) 0.020(2) 0.020(3) -0.003(2) -0.008(2) 0.002(2) N1B 0.021(3) 0.018(2) 0.016(3) -0.005(2) -0.004(2) 0.001(2) N6B 0.016(3) 0.017(2) 0.021(3) -0.006(2) -0.006(2) 0.0002(19) N8B 0.021(3) 0.016(2) 0.017(3) -0.002(2) -0.008(2) 0.001(2) N1C 0.014(3) 0.024(3) 0.021(3) -0.008(2) -0.005(2) 0.001(2) N6C 0.019(3) 0.013(2) 0.021(3) -0.006(2) -0.009(2) 0.0066(19) N8C 0.015(3) 0.016(2) 0.021(3) -0.005(2) -0.003(2) 0.0035(19) F1A 0.068(9) 0.041(5) 0.016(4) -0.009(3) -0.015(5) 0.007(5) F2A 0.058(5) 0.060(8) 0.026(7) -0.015(6) -0.005(4) 0.012(5) F3A 0.074(10) 0.046(6) 0.048(8) -0.021(5) -0.025(7) -0.012(6) F1AA 0.099(6) 0.062(9) 0.042(10) -0.033(8) 0.048(6) -0.028(6) F2AA 0.175(12) 0.068(8) 0.045(8) -0.032(6) -0.078(8) 0.058(9) F3AA 0.050(8) 0.024(4) 0.037(7) -0.015(4) -0.021(6) 0.003(4) F1B 0.038(2) 0.061(2) 0.027(2) 0.0033(17) -0.0075(17) -0.0250(18) F2B 0.049(2) 0.0360(19) 0.0251(19) -0.0138(16) -0.0075(17) -0.0003(16) F3B 0.045(2) 0.0289(19) 0.027(2) 0.0014(16) -0.0125(17) 0.0074(16) F1C 0.034(2) 0.0264(17) 0.040(2) -0.0076(16) -0.0235(16) 0.0079(15) F2C 0.035(2) 0.0348(19) 0.0281(19) -0.0155(16) -0.0116(16) 0.0065(15) F3C 0.0268(19) 0.041(2) 0.034(2) -0.0101(16) -0.0105(16) -0.0096(15) F11 0.032(6) 0.039(6) 0.023(6) -0.008(4) -0.002(4) 0.000(5) F12 0.031(5) 0.025(7) 0.022(6) -0.007(5) -0.008(5) -0.001(4) F13 0.049(8) 0.030(4) 0.040(6) -0.021(4) -0.014(5) 0.004(4) F11A 0.101(13) 0.033(6) 0.030(7) -0.020(6) -0.025(8) 0.022(7) F12A 0.044(6) 0.033(10) 0.048(8) 0.009(6) -0.031(6) -0.021(5) F13A 0.037(8) 0.041(8) 0.017(7) -0.007(6) 0.005(5) -0.004(7) C3A 0.029(4) 0.024(3) 0.024(4) -0.006(3) -0.007(3) -0.004(3) C4A 0.063(4) 0.031(3) 0.030(4) -0.007(3) -0.025(3) 0.006(3) C5A 0.030(4) 0.020(3) 0.023(3) 0.002(3) -0.014(3) -0.003(3) C6A 0.021(3) 0.023(3) 0.017(3) -0.002(3) -0.008(3) -0.001(3) C7A 0.018(3) 0.018(3) 0.020(3) -0.001(3) -0.007(3) -0.003(2) C10A 0.026(3) 0.020(3) 0.030(4) -0.008(3) -0.009(3) 0.004(3) C11A 0.027(4) 0.020(3) 0.035(4) -0.002(3) -0.016(3) 0.005(3) C12A 0.025(3) 0.022(3) 0.026(3) 0.003(3) -0.010(3) -0.001(3) C9A 0.017(3) 0.020(3) 0.025(3) -0.005(3) -0.008(3) -0.002(2) C13A 0.021(3) 0.016(3) 0.021(3) -0.003(3) -0.007(3) -0.001(2) C16A 0.023(3) 0.014(3) 0.021(3) -0.007(3) -0.003(3) -0.003(2) C17A 0.033(3) 0.025(3) 0.029(4) -0.011(3) -0.009(3) 0.001(2) C21A 0.024(3) 0.020(3) 0.025(3) -0.009(3) -0.006(3) 0.003(3) C1B 0.024(3) 0.013(3) 0.020(3) -0.003(2) -0.010(3) 0.000(2) C3B 0.027(3) 0.029(3) 0.030(4) -0.007(3) -0.009(3) -0.003(2) C4B 0.020(3) 0.016(3) 0.024(3) -0.004(3) -0.006(3) 0.000(2) C5B 0.018(3) 0.012(3) 0.023(3) -0.002(2) -0.009(3) 0.001(2) C7B 0.020(3) 0.013(3) 0.022(3) -0.007(2) -0.005(3) 0.000(2) C9B 0.032(4) 0.017(3) 0.025(4) -0.007(3) -0.012(3) 0.005(3) C10B 0.033(4) 0.019(3) 0.023(3) -0.005(3) -0.019(3) 0.007(3) C11B 0.023(3) 0.019(3) 0.039(4) -0.013(3) -0.014(3) 0.005(3) C12B 0.020(3) 0.021(3) 0.030(4) -0.010(3) -0.009(3) 0.002(2) C2C 0.018(3) 0.019(3) 0.025(3) -0.009(3) -0.008(3) 0.007(2) C3C 0.023(3) 0.021(3) 0.022(3) -0.006(2) -0.006(3) 0.001(2) C4C 0.019(3) 0.015(3) 0.024(3) -0.006(3) -0.006(3) 0.001(2) C5C 0.016(3) 0.014(3) 0.020(3) -0.003(2) -0.003(3) 0.003(2) C7C 0.015(3) 0.021(3) 0.022(3) -0.007(3) -0.004(3) 0.003(2) C9C 0.023(3) 0.025(3) 0.021(3) -0.008(3) -0.009(3) 0.002(3) C10C 0.024(3) 0.031(3) 0.018(3) -0.005(3) -0.003(3) 0.002(3) C11C 0.023(4) 0.024(3) 0.030(4) -0.001(3) -0.005(3) 0.003(3) C12C 0.021(3) 0.021(3) 0.025(3) -0.006(3) -0.008(3) 0.002(3) N1S 0.103(7) 0.195(9) 0.090(7) -0.063(7) -0.055(6) 0.053(6) C1S 0.053(6) 0.182(11) 0.061(7) -0.052(7) -0.011(5) 0.025(6) C2S 0.054(6) 0.277(15) 0.064(7) -0.050(8) -0.027(5) 0.021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N6B 1.977(4) . ? Cu1 N6C 1.989(4) . ? Cu1 N8C 2.056(4) . ? Cu1 N8B 2.133(4) . ? Cu1 N15A 2.163(4) . ? Cu2 N1A 1.951(4) . ? Cu2 N8A 1.987(4) . ? Cu2 N14A 2.036(4) . ? Cu2 N1B 2.066(4) . ? Cu2 N1C 2.141(4) . ? N1AA N1A 1.342(5) . ? N1AA C3A 1.340(6) . ? N1A C6A 1.350(6) . ? N8A C7A 1.340(6) . ? N8A C9A 1.356(6) . ? N14A N15A 1.355(5) . ? N14A C13A 1.358(6) . ? N15A C16A 1.371(6) . ? N1B N6B 1.343(5) . ? N1B C1B 1.358(6) . ? N6B C5B 1.344(6) . ? N8B C9B 1.337(6) . ? N8B C7B 1.360(6) . ? N1C N6C 1.353(5) . ? N1C C2C 1.363(6) . ? N6C C5C 1.346(6) . ? N8C C9C 1.347(6) . ? N8C C7C 1.365(6) . ? F1A C4A 1.324(7) . ? F2A C4A 1.371(8) . ? F3A C4A 1.326(8) . ? F1AA C4A 1.311(8) . ? F2AA C4A 1.354(8) . ? F3AA C4A 1.345(8) . ? F1B C3B 1.343(6) . ? F2B C3B 1.347(5) . ? F3B C3B 1.332(6) . ? F1C C3C 1.343(6) . ? F2C C3C 1.345(5) . ? F3C C3C 1.341(5) . ? F11 C17A 1.338(8) . ? F12 C17A 1.335(8) . ? F13 C17A 1.339(8) . ? F11A C17A 1.337(8) . ? F12A C17A 1.324(9) . ? F13A C17A 1.348(9) . ? C3A C5A 1.387(7) . ? C3A C4A 1.506(6) . ? C5A C6A 1.386(7) . ? C5A H5AA 0.9300 . ? C6A C7A 1.464(7) . ? C7A C12A 1.393(7) . ? C10A C11A 1.378(7) . ? C10A C9A 1.384(7) . ? C10A H10A 0.9300 . ? C11A C12A 1.389(7) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C9A C13A 1.455(7) . ? C13A C21A 1.385(7) . ? C16A C21A 1.382(7) . ? C16A C17A 1.500(6) . ? C21A H21A 0.9300 . ? C1B C4B 1.370(7) . ? C1B C3B 1.491(7) . ? C4B C5B 1.387(7) . ? C4B H4BA 0.9300 . ? C5B C7B 1.453(7) . ? C7B C12B 1.380(7) . ? C9B C10B 1.378(7) . ? C9B H9BA 0.9300 . ? C10B C11B 1.372(7) . ? C10B H10B 0.9300 . ? C11B C12B 1.378(7) . ? C11B H11B 0.9300 . ? C12B H12B 0.9300 . ? C2C C4C 1.388(7) . ? C2C C3C 1.479(7) . ? C4C C5C 1.391(7) . ? C4C H4CA 0.9300 . ? C5C C7C 1.445(7) . ? C7C C12C 1.384(7) . ? C9C C10C 1.370(7) . ? C9C H9CA 0.9300 . ? C10C C11C 1.380(7) . ? C10C H10C 0.9300 . ? C11C C12C 1.372(7) . ? C11C H11C 0.9300 . ? C12C H12C 0.9300 . ? N1S C1S 1.147(10) . ? C1S C2S 1.417(12) . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9600 . ? C2S H2SC 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 N6B Cu1 N6C 94.09(17) . . ? N6B Cu1 N8C 164.16(15) . . ? N6C Cu1 N8C 79.40(17) . . ? N6B Cu1 N8B 79.10(17) . . ? N6C Cu1 N8B 151.56(15) . . ? N8C Cu1 N8B 99.71(16) . . ? N6B Cu1 N15A 89.96(16) . . ? N6C Cu1 N15A 91.16(15) . . ? N8C Cu1 N15A 104.49(15) . . ? N8B Cu1 N15A 116.19(14) . . ? N1A Cu2 N8A 79.63(18) . . ? N1A Cu2 N14A 157.44(18) . . ? N8A Cu2 N14A 77.82(17) . . ? N1A Cu2 N1B 103.16(17) . . ? N8A Cu2 N1B 134.36(15) . . ? N14A Cu2 N1B 93.10(16) . . ? N1A Cu2 N1C 101.06(16) . . ? N8A Cu2 N1C 129.72(16) . . ? N14A Cu2 N1C 92.87(16) . . ? N1B Cu2 N1C 94.96(16) . . ? N1A N1AA C3A 105.2(4) . . ? N1AA N1A C6A 110.2(4) . . ? N1AA N1A Cu2 133.1(4) . . ? C6A N1A Cu2 116.4(3) . . ? C7A N8A C9A 122.6(5) . . ? C7A N8A Cu2 117.6(3) . . ? C9A N8A Cu2 119.8(4) . . ? N15A N14A C13A 110.5(4) . . ? N15A N14A Cu2 133.7(3) . . ? C13A N14A Cu2 115.8(3) . . ? N14A N15A C16A 104.6(4) . . ? N14A N15A Cu1 111.2(3) . . ? C16A N15A Cu1 144.1(4) . . ? N6B N1B C1B 105.1(4) . . ? N6B N1B Cu2 115.1(3) . . ? C1B N1B Cu2 137.4(4) . . ? N1B N6B C5B 110.7(4) . . ? N1B N6B Cu1 132.0(3) . . ? C5B N6B Cu1 117.3(4) . . ? C9B N8B C7B 116.9(4) . . ? C9B N8B Cu1 130.6(4) . . ? C7B N8B Cu1 112.4(3) . . ? N6C N1C C2C 105.8(4) . . ? N6C N1C Cu2 111.2(3) . . ? C2C N1C Cu2 140.1(4) . . ? C5C N6C N1C 110.1(4) . . ? C5C N6C Cu1 115.4(4) . . ? N1C N6C Cu1 134.4(3) . . ? C9C N8C C7C 117.5(4) . . ? C9C N8C Cu1 129.3(3) . . ? C7C N8C Cu1 112.6(3) . . ? N1AA C3A C5A 113.0(4) . . ? N1AA C3A C4A 118.6(5) . . ? C5A C3A C4A 128.4(5) . . ? F1AA C4A F1A 80.5(9) . . ? F1AA C4A F3A 116.9(14) . . ? F1A C4A F3A 110.9(9) . . ? F1AA C4A F3AA 106.6(9) . . ? F1A C4A F3AA 126.2(10) . . ? F3A C4A F3AA 18.3(14) . . ? F1AA C4A F2AA 111.3(8) . . ? F1A C4A F2AA 33.2(9) . . ? F3A C4A F2AA 85.6(11) . . ? F3AA C4A F2AA 103.6(10) . . ? F1AA C4A F2A 24.5(10) . . ? F1A C4A F2A 104.7(7) . . ? F3A C4A F2A 104.1(9) . . ? F3AA C4A F2A 89.4(12) . . ? F2AA C4A F2A 133.7(10) . . ? F1AA C4A C3A 116.4(8) . . ? F1A C4A C3A 113.0(6) . . ? F3A C4A C3A 114.4(10) . . ? F3AA C4A C3A 110.6(9) . . ? F2AA C4A C3A 107.6(7) . . ? F2A C4A C3A 108.8(7) . . ? C6A C5A C3A 102.2(5) . . ? C6A C5A H5AA 128.9 . . ? C3A C5A H5AA 128.9 . . ? N1A C6A C5A 109.4(5) . . ? N1A C6A C7A 114.9(5) . . ? C5A C6A C7A 135.6(5) . . ? N8A C7A C12A 119.6(5) . . ? N8A C7A C6A 111.3(5) . . ? C12A C7A C6A 129.1(5) . . ? C11A C10A C9A 118.6(5) . . ? C11A C10A H10A 120.7 . . ? C9A C10A H10A 120.7 . . ? C10A C11A C12A 121.1(5) . . ? C10A C11A H11A 119.4 . . ? C12A C11A H11A 119.4 . . ? C11A C12A C7A 118.4(5) . . ? C11A C12A H12A 120.8 . . ? C7A C12A H12A 120.8 . . ? N8A C9A C10A 119.7(5) . . ? N8A C9A C13A 111.4(5) . . ? C10A C9A C13A 128.9(5) . . ? N14A C13A C21A 109.0(5) . . ? N14A C13A C9A 115.1(4) . . ? C21A C13A C9A 135.8(5) . . ? N15A C16A C21A 112.1(4) . . ? N15A C16A C17A 117.1(4) . . ? C21A C16A C17A 130.7(4) . . ? F12A C17A F12 15.2(16) . . ? F12A C17A F11A 109.2(10) . . ? F12 C17A F11A 121.9(15) . . ? F12A C17A F11 117.2(16) . . ? F12 C17A F11 106.2(9) . . ? F11A C17A F11 91.6(16) . . ? F12A C17A F13 92.9(14) . . ? F12 C17A F13 107.0(8) . . ? F11A C17A F13 19.2(16) . . ? F11 C17A F13 108.5(9) . . ? F12A C17A F13A 106.0(11) . . ? F12 C17A F13A 93.4(15) . . ? F11A C17A F13A 106.1(11) . . ? F11 C17A F13A 15.6(18) . . ? F13 C17A F13A 121.8(14) . . ? F12A C17A C16A 113.6(10) . . ? F12 C17A C16A 112.1(7) . . ? F11A C17A C16A 110.5(9) . . ? F11 C17A C16A 112.5(9) . . ? F13 C17A C16A 110.2(8) . . ? F13A C17A C16A 111.1(11) . . ? C16A C21A C13A 103.8(4) . . ? C16A C21A H21A 128.1 . . ? C13A C21A H21A 128.1 . . ? N1B C1B C4B 111.8(5) . . ? N1B C1B C3B 121.6(5) . . ? C4B C1B C3B 126.6(5) . . ? F3B C3B F1B 107.1(4) . . ? F3B C3B F2B 106.1(4) . . ? F1B C3B F2B 105.6(4) . . ? F3B C3B C1B 113.8(5) . . ? F1B C3B C1B 110.6(4) . . ? F2B C3B C1B 113.0(4) . . ? C1B C4B C5B 103.9(5) . . ? C1B C4B H4BA 128.0 . . ? C5B C4B H4BA 128.0 . . ? N6B C5B C4B 108.5(5) . . ? N6B C5B C7B 116.5(5) . . ? C4B C5B C7B 135.0(5) . . ? N8B C7B C12B 121.4(5) . . ? N8B C7B C5B 114.6(5) . . ? C12B C7B C5B 124.0(5) . . ? N8B C9B C10B 124.3(5) . . ? N8B C9B H9BA 117.9 . . ? C10B C9B H9BA 117.9 . . ? C11B C10B C9B 118.7(5) . . ? C11B C10B H10B 120.7 . . ? C9B C10B H10B 120.7 . . ? C10B C11B C12B 118.1(5) . . ? C10B C11B H11B 121.0 . . ? C12B C11B H11B 121.0 . . ? C11B C12B C7B 120.7(5) . . ? C11B C12B H12B 119.6 . . ? C7B C12B H12B 119.6 . . ? N1C C2C C4C 111.0(5) . . ? N1C C2C C3C 121.6(5) . . ? C4C C2C C3C 127.3(5) . . ? F3C C3C F2C 105.4(4) . . ? F3C C3C F1C 106.5(4) . . ? F2C C3C F1C 106.4(4) . . ? F3C C3C C2C 110.6(4) . . ? F2C C3C C2C 113.8(4) . . ? F1C C3C C2C 113.5(4) . . ? C2C C4C C5C 103.9(4) . . ? C2C C4C H4CA 128.0 . . ? C5C C4C H4CA 128.0 . . ? N6C C5C C4C 109.1(5) . . ? N6C C5C C7C 115.6(4) . . ? C4C C5C C7C 134.7(5) . . ? N8C C7C C12C 120.8(5) . . ? N8C C7C C5C 113.9(4) . . ? C12C C7C C5C 125.2(5) . . ? N8C C9C C10C 123.9(5) . . ? N8C C9C H9CA 118.1 . . ? C10C C9C H9CA 118.1 . . ? C9C C10C C11C 117.8(5) . . ? C9C C10C H10C 121.1 . . ? C11C C10C H10C 121.1 . . ? C12C C11C C10C 119.6(5) . . ? C12C C11C H11C 120.2 . . ? C10C C11C H11C 120.2 . . ? C11C C12C C7C 119.9(5) . . ? C11C C12C H12C 120.0 . . ? C7C C12C H12C 120.0 . . ? N1S C1S C2S 178.1(13) . . ? C1S C2S H2SA 109.5 . . ? C1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? C1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.847 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.116 data_zzzs _database_code_depnum_ccdc_archive 'CCDC 910211' #TrackingRef 'web_deposit_cif_file_0_GalinaRomanenko_1355844366.all(295-150-103)_last (1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H18 Cu2 F12 N12' _chemical_formula_weight 937.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2169(2) _cell_length_b 14.1322(3) _cell_length_c 14.4655(3) _cell_angle_alpha 76.5540(10) _cell_angle_beta 73.5810(10) _cell_angle_gamma 87.2240(10) _cell_volume 1757.53(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9973 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 64.83 _exptl_crystal_description box _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 2.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3372 _exptl_absorpt_correction_T_max 0.4524 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20337 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 62.50 _reflns_number_total 5526 _reflns_number_gt 4946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+1.1136P] 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 5526 _refine_ls_number_parameters 588 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.129 _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 0.04059(4) 0.20285(3) 0.52993(3) 0.03760(14) Uani 1 1 d . . . Cu2 Cu -0.05876(5) 0.30914(3) 0.30616(3) 0.04504(15) Uani 1 1 d . . . N1AA N 0.0183(3) 0.2404(2) 0.1143(2) 0.0555(7) Uani 1 1 d . . . N1A N -0.0434(3) 0.30323(19) 0.16971(19) 0.0496(6) Uani 1 1 d . . . N8A N -0.1792(3) 0.42459(17) 0.26728(19) 0.0438(6) Uani 1 1 d . A . N14A N -0.1244(3) 0.35961(17) 0.43202(18) 0.0431(6) Uani 1 1 d . . . N15A N -0.0975(3) 0.33388(17) 0.52139(18) 0.0438(6) Uani 1 1 d . . . N1B N 0.1667(3) 0.29829(17) 0.31060(17) 0.0409(5) Uani 1 1 d . . . N6B N 0.1833(3) 0.26379(16) 0.40194(17) 0.0385(5) Uani 1 1 d . . . N8B N 0.2412(3) 0.21157(17) 0.57344(18) 0.0414(5) Uani 1 1 d . . . N1C N -0.1230(3) 0.16332(17) 0.38293(17) 0.0395(5) Uani 1 1 d . . . N6C N -0.0875(3) 0.14054(16) 0.46970(17) 0.0381(5) Uani 1 1 d . . . N8C N -0.0821(3) 0.10437(17) 0.65277(17) 0.0416(5) Uani 1 1 d . . . F1A F 0.0444(15) 0.2698(7) -0.1390(4) 0.102(3) Uani 0.52(2) 1 d PDU A 3 F2A F 0.1817(10) 0.1890(12) -0.0597(8) 0.124(4) Uani 0.52(2) 1 d PDU A 3 F3A F -0.039(2) 0.1369(9) -0.0342(12) 0.154(7) Uani 0.52(2) 1 d PDU A 3 F1AA F 0.1802(12) 0.2236(11) -0.0937(13) 0.141(5) Uani 0.48(2) 1 d PDU A 4 F2AA F -0.045(3) 0.2434(12) -0.1151(12) 0.149(5) Uani 0.48(2) 1 d PDU A 4 F3AA F 0.0003(17) 0.1241(5) -0.0151(10) 0.100(3) Uani 0.48(2) 1 d PDU A 4 F1B F 0.4574(3) 0.4306(3) 0.11072(18) 0.1194(12) Uani 1 1 d U . . F2B F 0.3345(3) 0.3174(2) 0.09154(17) 0.0954(8) Uani 1 1 d U . . F3B F 0.2202(3) 0.44219(18) 0.12777(17) 0.0891(7) Uani 1 1 d U . . F1C F -0.3224(3) 0.18506(16) 0.26343(18) 0.0762(6) Uani 1 1 d U . . F2C F -0.2067(3) 0.05624(18) 0.23557(16) 0.0753(6) Uani 1 1 d U . . F3C F -0.4217(3) 0.0446(2) 0.34122(18) 0.0848(7) Uani 1 1 d U . . F11 F -0.2758(13) 0.3482(14) 0.7440(8) 0.142(6) Uani 0.505(19) 1 d PDU B 1 F12 F -0.0404(12) 0.3399(8) 0.6914(9) 0.103(4) Uani 0.505(19) 1 d PDU B 1 F13 F -0.1353(13) 0.4754(5) 0.6907(7) 0.088(3) Uani 0.505(19) 1 d PDU B 1 F11A F -0.225(3) 0.4615(9) 0.7139(8) 0.134(5) Uani 0.495(19) 1 d PDU B 2 F12A F -0.0273(9) 0.3714(12) 0.6880(9) 0.111(4) Uani 0.495(19) 1 d PDU B 2 F13A F -0.2473(15) 0.3139(8) 0.7335(7) 0.100(3) Uani 0.495(19) 1 d PDU B 2 C3A C -0.0154(4) 0.2737(3) 0.0283(2) 0.0560(8) Uani 1 1 d D A . C4A C 0.0370(5) 0.2172(3) -0.0495(3) 0.0790(11) Uani 1 1 d DU . . C5A C -0.0995(4) 0.3572(3) 0.0275(2) 0.0581(9) Uani 1 1 d . . . H5AA H -0.1364 0.3929 -0.0234 0.070 Uiso 1 1 calc R A . C6A C -0.1159(4) 0.3751(2) 0.1189(2) 0.0468(7) Uani 1 1 d . A . C7A C -0.1914(3) 0.4454(2) 0.1745(2) 0.0469(7) Uani 1 1 d . . . C10A C -0.3269(4) 0.5583(2) 0.3064(3) 0.0615(9) Uani 1 1 d . A . H10A H -0.3731 0.5955 0.3515 0.074 Uiso 1 1 calc R . . C11A C -0.3408(5) 0.5812(3) 0.2112(3) 0.0690(10) Uani 1 1 d . . . H11A H -0.3977 0.6344 0.1922 0.083 Uiso 1 1 calc R A . C12A C -0.2720(4) 0.5267(3) 0.1438(3) 0.0609(9) Uani 1 1 d . A . H12A H -0.2792 0.5439 0.0792 0.073 Uiso 1 1 calc R . . C9A C -0.2419(3) 0.4779(2) 0.3328(2) 0.0474(7) Uani 1 1 d . . . C13A C -0.2077(3) 0.4409(2) 0.4273(2) 0.0449(7) Uani 1 1 d . A . C16A C -0.1661(3) 0.3997(2) 0.5718(2) 0.0462(7) Uani 1 1 d D A . C17A C -0.1606(4) 0.3892(2) 0.6752(3) 0.0623(9) Uani 1 1 d DU . . C21A C -0.2373(4) 0.4688(2) 0.5159(2) 0.0522(8) Uani 1 1 d . . . H21A H -0.2924 0.5217 0.5339 0.063 Uiso 1 1 calc R A . C1B C 0.3024(3) 0.3358(2) 0.2533(2) 0.0442(7) Uani 1 1 d . . . C3B C 0.3290(4) 0.3820(3) 0.1465(3) 0.0618(9) Uani 1 1 d U . . C4B C 0.4070(3) 0.3256(2) 0.3067(2) 0.0490(7) Uani 1 1 d . . . H4BA H 0.5082 0.3453 0.2844 0.059 Uiso 1 1 calc R . . C5B C 0.3262(3) 0.2792(2) 0.4011(2) 0.0403(6) Uani 1 1 d . . . C7B C 0.3610(3) 0.2475(2) 0.4957(2) 0.0402(6) Uani 1 1 d . . . C9B C 0.2681(4) 0.1823(3) 0.6619(3) 0.0551(8) Uani 1 1 d . . . H9BA H 0.1872 0.1576 0.7164 0.066 Uiso 1 1 calc R . . C10B C 0.4081(4) 0.1864(3) 0.6770(3) 0.0598(9) Uani 1 1 d . . . H10B H 0.4205 0.1656 0.7402 0.072 Uiso 1 1 calc R . . C11B C 0.5291(4) 0.2219(2) 0.5973(3) 0.0563(9) Uani 1 1 d . . . H11B H 0.6254 0.2247 0.6053 0.068 Uiso 1 1 calc R . . C12B C 0.5057(3) 0.2532(2) 0.5056(3) 0.0505(8) Uani 1 1 d . . . H12B H 0.5859 0.2780 0.4506 0.061 Uiso 1 1 calc R . . C2C C -0.2226(3) 0.0937(2) 0.3885(2) 0.0413(6) Uani 1 1 d . . . C3C C -0.2917(4) 0.0956(2) 0.3071(3) 0.0522(8) Uani 1 1 d U . . C4C C -0.2517(3) 0.0265(2) 0.4777(2) 0.0441(7) Uani 1 1 d . . . H4CA H -0.3151 -0.0282 0.4994 0.053 Uiso 1 1 calc R . . C5C C -0.1633(3) 0.06002(19) 0.5277(2) 0.0384(6) Uani 1 1 d . . . C7C C -0.1525(3) 0.0350(2) 0.6291(2) 0.0396(6) Uani 1 1 d . . . C9C C -0.0860(4) 0.0935(3) 0.7476(2) 0.0516(8) Uani 1 1 d . . . H9CA H -0.0467 0.1436 0.7657 0.062 Uiso 1 1 calc R . . C10C C -0.1448(4) 0.0126(3) 0.8195(3) 0.0593(9) Uani 1 1 d . . . H10C H -0.1432 0.0075 0.8845 0.071 Uiso 1 1 calc R . . C11C C -0.2067(4) -0.0614(3) 0.7938(3) 0.0609(9) Uani 1 1 d . . . H11C H -0.2423 -0.1187 0.8404 0.073 Uiso 1 1 calc R . . C12C C -0.2146(4) -0.0486(2) 0.6981(2) 0.0505(7) Uani 1 1 d . . . H12C H -0.2612 -0.0955 0.6801 0.061 Uiso 1 1 calc R . . N1S N -0.4997(15) 0.1287(15) -0.0889(9) 0.356(11) Uani 1 1 d . . . C1S C -0.4474(11) 0.1369(11) -0.0260(9) 0.214(5) Uani 1 1 d . . . C2S C -0.3983(10) 0.1149(15) 0.0580(8) 0.335(12) Uani 1 1 d . . . H2SA H -0.3450 0.1702 0.0615 0.503 Uiso 1 1 calc R . . H2SB H -0.3318 0.0605 0.0557 0.503 Uiso 1 1 calc R . . H2SC H -0.4838 0.0987 0.1154 0.503 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 0.0387(2) 0.0390(2) 0.0348(2) -0.00911(18) -0.00875(18) -0.00258(17) Cu2 0.0554(3) 0.0455(3) 0.0382(3) -0.0145(2) -0.0176(2) 0.0150(2) N1AA 0.0697(18) 0.0593(17) 0.0421(15) -0.0179(13) -0.0195(13) 0.0123(14) N1A 0.0621(16) 0.0490(15) 0.0414(14) -0.0123(12) -0.0200(12) 0.0104(12) N8A 0.0458(13) 0.0407(13) 0.0460(14) -0.0098(11) -0.0151(11) 0.0041(11) N14A 0.0501(14) 0.0390(13) 0.0421(14) -0.0150(11) -0.0129(11) 0.0104(11) N15A 0.0517(14) 0.0400(13) 0.0410(14) -0.0141(11) -0.0119(11) 0.0051(11) N1B 0.0449(13) 0.0400(13) 0.0357(13) -0.0074(10) -0.0087(10) -0.0014(10) N6B 0.0396(13) 0.0379(13) 0.0366(13) -0.0074(10) -0.0091(10) -0.0019(10) N8B 0.0458(13) 0.0374(13) 0.0424(14) -0.0099(10) -0.0136(11) -0.0015(10) N1C 0.0424(13) 0.0370(12) 0.0410(13) -0.0118(10) -0.0124(10) 0.0006(10) N6C 0.0407(12) 0.0367(12) 0.0381(13) -0.0129(10) -0.0094(10) 0.0017(10) N8C 0.0426(13) 0.0419(13) 0.0379(13) -0.0097(10) -0.0072(10) 0.0008(10) F1A 0.150(7) 0.117(5) 0.040(3) -0.026(3) -0.022(4) 0.009(5) F2A 0.129(5) 0.173(10) 0.089(6) -0.069(6) -0.041(5) 0.067(6) F3A 0.209(12) 0.147(10) 0.116(10) -0.076(8) -0.012(8) -0.068(9) F1AA 0.155(6) 0.128(9) 0.107(9) -0.063(7) 0.047(6) -0.019(6) F2AA 0.264(12) 0.149(9) 0.087(7) -0.065(6) -0.112(8) 0.078(9) F3AA 0.172(8) 0.061(4) 0.084(5) -0.039(3) -0.045(5) 0.012(4) F1B 0.106(2) 0.171(3) 0.0579(15) 0.0271(16) -0.0160(14) -0.079(2) F2B 0.130(2) 0.1010(19) 0.0510(13) -0.0288(13) -0.0086(13) -0.0043(16) F3B 0.118(2) 0.0820(16) 0.0601(14) 0.0061(12) -0.0342(13) 0.0145(14) F1C 0.0890(15) 0.0668(13) 0.0929(16) -0.0208(12) -0.0579(13) 0.0174(11) F2C 0.0839(14) 0.0943(16) 0.0648(13) -0.0448(12) -0.0291(11) 0.0182(12) F3C 0.0665(13) 0.1138(19) 0.0840(16) -0.0255(14) -0.0291(12) -0.0293(13) F11 0.113(6) 0.245(16) 0.058(4) -0.047(7) 0.015(4) -0.081(9) F12 0.167(8) 0.096(5) 0.079(6) -0.052(5) -0.072(6) 0.068(6) F13 0.129(6) 0.074(3) 0.077(4) -0.049(3) -0.027(4) -0.009(3) F11A 0.245(12) 0.097(6) 0.081(5) -0.064(5) -0.060(7) 0.085(7) F12A 0.082(4) 0.182(10) 0.070(5) -0.007(6) -0.034(4) -0.040(5) F13A 0.156(7) 0.098(5) 0.032(4) -0.007(3) -0.002(4) -0.037(4) C3A 0.073(2) 0.061(2) 0.0366(17) -0.0123(15) -0.0186(16) -0.0014(17) C4A 0.115(3) 0.078(3) 0.052(2) -0.0230(19) -0.031(2) 0.011(2) C5A 0.075(2) 0.059(2) 0.0439(19) -0.0040(16) -0.0298(17) 0.0011(17) C6A 0.0511(17) 0.0445(17) 0.0455(17) -0.0040(14) -0.0187(14) -0.0036(13) C7A 0.0470(17) 0.0417(16) 0.0519(19) -0.0031(14) -0.0191(14) -0.0036(13) C10A 0.068(2) 0.0445(18) 0.073(2) -0.0158(17) -0.0231(19) 0.0154(16) C11A 0.075(2) 0.049(2) 0.085(3) -0.0061(19) -0.035(2) 0.0184(18) C12A 0.068(2) 0.052(2) 0.064(2) -0.0024(17) -0.0308(18) 0.0077(17) C9A 0.0461(16) 0.0378(16) 0.0576(19) -0.0101(14) -0.0143(14) 0.0014(13) C13A 0.0451(16) 0.0367(15) 0.0517(18) -0.0121(13) -0.0104(14) 0.0017(12) C16A 0.0522(17) 0.0391(16) 0.0470(17) -0.0185(14) -0.0061(14) -0.0002(13) C17A 0.083(2) 0.054(2) 0.054(2) -0.0258(16) -0.0146(18) 0.0030(17) C21A 0.060(2) 0.0402(17) 0.057(2) -0.0214(15) -0.0109(16) 0.0104(14) C1B 0.0488(17) 0.0408(16) 0.0380(16) -0.0063(13) -0.0057(13) -0.0030(13) C3B 0.068(2) 0.068(2) 0.0429(19) -0.0047(16) -0.0080(16) -0.0147(17) C4B 0.0385(15) 0.0524(18) 0.0498(19) -0.0074(15) -0.0045(14) -0.0064(13) C5B 0.0362(15) 0.0373(15) 0.0478(17) -0.0134(13) -0.0100(13) 0.0022(11) C7B 0.0426(15) 0.0315(14) 0.0487(17) -0.0129(12) -0.0136(13) 0.0028(11) C9B 0.058(2) 0.059(2) 0.0487(19) -0.0076(15) -0.0186(16) -0.0045(16) C10B 0.073(2) 0.056(2) 0.063(2) -0.0150(17) -0.039(2) 0.0051(17) C11B 0.0523(19) 0.0510(19) 0.079(3) -0.0227(17) -0.0337(19) 0.0080(15) C12B 0.0392(16) 0.0499(18) 0.066(2) -0.0173(16) -0.0159(15) -0.0002(13) C2C 0.0401(15) 0.0399(15) 0.0481(17) -0.0184(13) -0.0124(13) 0.0030(12) C3C 0.0481(17) 0.0547(19) 0.061(2) -0.0224(16) -0.0185(15) 0.0021(14) C4C 0.0421(16) 0.0379(16) 0.0525(18) -0.0152(14) -0.0086(13) -0.0042(12) C5C 0.0376(14) 0.0333(14) 0.0417(16) -0.0128(12) -0.0042(12) 0.0043(11) C7C 0.0394(15) 0.0343(15) 0.0422(16) -0.0119(12) -0.0050(12) 0.0063(11) C9C 0.0539(18) 0.060(2) 0.0410(18) -0.0156(15) -0.0097(14) 0.0000(15) C10C 0.062(2) 0.069(2) 0.0401(18) -0.0046(16) -0.0106(15) 0.0021(17) C11C 0.063(2) 0.052(2) 0.054(2) 0.0057(16) -0.0080(17) 0.0006(16) C12C 0.0540(18) 0.0375(16) 0.0528(19) -0.0060(14) -0.0068(15) -0.0013(13) N1S 0.254(12) 0.67(3) 0.214(11) -0.196(16) -0.139(10) 0.209(16) C1S 0.111(6) 0.360(17) 0.167(10) -0.089(11) -0.018(6) 0.059(8) C2S 0.108(6) 0.79(4) 0.147(9) -0.172(15) -0.056(6) 0.063(12) _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 N6B 1.973(2) . ? Cu1 N6C 1.992(2) . ? Cu1 N8C 2.059(2) . ? Cu1 N8B 2.132(2) . ? Cu1 N15A 2.195(2) . ? Cu2 N1A 1.960(3) . ? Cu2 N8A 1.990(2) . ? Cu2 N14A 2.032(2) . ? Cu2 N1B 2.094(2) . ? Cu2 N1C 2.124(2) . ? N1AA N1A 1.334(4) . ? N1AA C3A 1.340(4) . ? N1A C6A 1.372(4) . ? N8A C9A 1.335(4) . ? N8A C7A 1.341(4) . ? N14A N15A 1.349(3) . ? N14A C13A 1.349(4) . ? N15A C16A 1.339(4) . ? N1B C1B 1.344(4) . ? N1B N6B 1.347(3) . ? N6B C5B 1.342(4) . ? N8B C9B 1.339(4) . ? N8B C7B 1.353(4) . ? N1C N6C 1.349(3) . ? N1C C2C 1.352(4) . ? N6C C5C 1.338(4) . ? N8C C9C 1.335(4) . ? N8C C7C 1.357(4) . ? F1A C4A 1.319(7) . ? F2A C4A 1.351(8) . ? F3A C4A 1.304(8) . ? F1AA C4A 1.291(8) . ? F2AA C4A 1.349(8) . ? F3AA C4A 1.318(8) . ? F1B C3B 1.307(4) . ? F2B C3B 1.333(4) . ? F3B C3B 1.329(5) . ? F1C C3C 1.331(4) . ? F2C C3C 1.327(4) . ? F3C C3C 1.335(4) . ? F11 C17A 1.284(7) . ? F12 C17A 1.329(7) . ? F13 C17A 1.332(6) . ? F11A C17A 1.315(6) . ? F12A C17A 1.298(7) . ? F13A C17A 1.329(7) . ? C3A C5A 1.379(5) . ? C3A C4A 1.487(5) . ? C5A C6A 1.370(5) . ? C5A H5AA 0.9300 . ? C6A C7A 1.451(5) . ? C7A C12A 1.391(4) . ? C10A C11A 1.380(5) . ? C10A C9A 1.389(4) . ? C10A H10A 0.9300 . ? C11A C12A 1.377(6) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C9A C13A 1.462(4) . ? C13A C21A 1.379(5) . ? C16A C21A 1.381(5) . ? C16A C17A 1.483(4) . ? C21A H21A 0.9300 . ? C1B C4B 1.380(4) . ? C1B C3B 1.485(5) . ? C4B C5B 1.380(4) . ? C4B H4BA 0.9300 . ? C5B C7B 1.457(4) . ? C7B C12B 1.389(4) . ? C9B C10B 1.374(5) . ? C9B H9BA 0.9300 . ? C10B C11B 1.373(5) . ? C10B H10B 0.9300 . ? C11B C12B 1.372(5) . ? C11B H11B 0.9300 . ? C12B H12B 0.9300 . ? C2C C4C 1.378(4) . ? C2C C3C 1.483(4) . ? C4C C5C 1.393(4) . ? C4C H4CA 0.9300 . ? C5C C7C 1.457(4) . ? C7C C12C 1.383(4) . ? C9C C10C 1.367(5) . ? C9C H9CA 0.9300 . ? C10C C11C 1.385(5) . ? C10C H10C 0.9300 . ? C11C C12C 1.376(5) . ? C11C H11C 0.9300 . ? C12C H12C 0.9300 . ? N1S C1S 1.174(14) . ? C1S C2S 1.379(14) . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9600 . ? C2S H2SC 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 N6B Cu1 N6C 94.45(9) . . ? N6B Cu1 N8C 164.00(10) . . ? N6C Cu1 N8C 79.55(9) . . ? N6B Cu1 N8B 79.07(9) . . ? N6C Cu1 N8B 151.86(9) . . ? N8C Cu1 N8B 99.18(9) . . ? N6B Cu1 N15A 89.84(9) . . ? N6C Cu1 N15A 90.88(9) . . ? N8C Cu1 N15A 104.97(9) . . ? N8B Cu1 N15A 116.23(9) . . ? N1A Cu2 N8A 79.79(10) . . ? N1A Cu2 N14A 157.67(10) . . ? N8A Cu2 N14A 77.90(10) . . ? N1A Cu2 N1B 102.92(10) . . ? N8A Cu2 N1B 130.86(10) . . ? N14A Cu2 N1B 92.29(10) . . ? N1A Cu2 N1C 101.31(10) . . ? N8A Cu2 N1C 132.01(10) . . ? N14A Cu2 N1C 93.09(9) . . ? N1B Cu2 N1C 96.12(9) . . ? N1A N1AA C3A 105.2(3) . . ? N1AA N1A C6A 110.5(3) . . ? N1AA N1A Cu2 133.6(2) . . ? C6A N1A Cu2 115.8(2) . . ? C9A N8A C7A 123.2(3) . . ? C9A N8A Cu2 119.5(2) . . ? C7A N8A Cu2 117.3(2) . . ? N15A N14A C13A 109.4(2) . . ? N15A N14A Cu2 134.78(18) . . ? C13A N14A Cu2 115.7(2) . . ? C16A N15A N14A 106.3(2) . . ? C16A N15A Cu1 143.7(2) . . ? N14A N15A Cu1 109.96(17) . . ? C1B N1B N6B 106.0(2) . . ? C1B N1B Cu2 137.7(2) . . ? N6B N1B Cu2 114.10(17) . . ? C5B N6B N1B 109.7(2) . . ? C5B N6B Cu1 117.50(19) . . ? N1B N6B Cu1 132.75(18) . . ? C9B N8B C7B 116.6(3) . . ? C9B N8B Cu1 130.8(2) . . ? C7B N8B Cu1 112.41(18) . . ? N6C N1C C2C 105.8(2) . . ? N6C N1C Cu2 111.46(16) . . ? C2C N1C Cu2 139.57(19) . . ? C5C N6C N1C 110.0(2) . . ? C5C N6C Cu1 115.37(19) . . ? N1C N6C Cu1 134.49(18) . . ? C9C N8C C7C 117.6(3) . . ? C9C N8C Cu1 129.2(2) . . ? C7C N8C Cu1 112.65(19) . . ? N1AA C3A C5A 112.5(3) . . ? N1AA C3A C4A 117.9(3) . . ? C5A C3A C4A 129.5(3) . . ? F1AA C4A F3A 120.8(11) . . ? F1AA C4A F3AA 107.6(8) . . ? F3A C4A F3AA 22.7(11) . . ? F1AA C4A F1A 76.5(8) . . ? F3A C4A F1A 109.3(8) . . ? F3AA C4A F1A 127.0(8) . . ? F1AA C4A F2AA 111.2(8) . . ? F3A C4A F2AA 79.0(9) . . ? F3AA C4A F2AA 101.1(9) . . ? F1A C4A F2AA 37.7(8) . . ? F1AA C4A F2A 26.6(8) . . ? F3A C4A F2A 104.5(9) . . ? F3AA C4A F2A 86.0(10) . . ? F1A C4A F2A 101.8(6) . . ? F2AA C4A F2A 132.3(9) . . ? F1AA C4A C3A 115.4(7) . . ? F3A C4A C3A 115.3(8) . . ? F3AA C4A C3A 112.1(7) . . ? F1A C4A C3A 112.8(5) . . ? F2AA C4A C3A 108.5(6) . . ? F2A C4A C3A 112.1(6) . . ? C6A C5A C3A 104.0(3) . . ? C6A C5A H5AA 128.0 . . ? C3A C5A H5AA 128.0 . . ? C5A C6A N1A 107.9(3) . . ? C5A C6A C7A 137.4(3) . . ? N1A C6A C7A 114.6(3) . . ? N8A C7A C12A 119.1(3) . . ? N8A C7A C6A 112.4(3) . . ? C12A C7A C6A 128.5(3) . . ? C11A C10A C9A 118.0(3) . . ? C11A C10A H10A 121.0 . . ? C9A C10A H10A 121.0 . . ? C12A C11A C10A 121.3(3) . . ? C12A C11A H11A 119.3 . . ? C10A C11A H11A 119.3 . . ? C11A C12A C7A 118.6(3) . . ? C11A C12A H12A 120.7 . . ? C7A C12A H12A 120.7 . . ? N8A C9A C10A 119.8(3) . . ? N8A C9A C13A 112.0(3) . . ? C10A C9A C13A 128.2(3) . . ? N14A C13A C21A 109.1(3) . . ? N14A C13A C9A 114.9(3) . . ? C21A C13A C9A 136.1(3) . . ? N15A C16A C21A 111.4(3) . . ? N15A C16A C17A 119.2(3) . . ? C21A C16A C17A 129.4(3) . . ? F11 C17A F12A 118.3(10) . . ? F11 C17A F11A 76.7(8) . . ? F12A C17A F11A 112.1(8) . . ? F11 C17A F12 106.5(8) . . ? F12A C17A F12 19.9(8) . . ? F11A C17A F12 127.5(8) . . ? F11 C17A F13A 25.2(10) . . ? F12A C17A F13A 105.4(7) . . ? F11A C17A F13A 101.7(8) . . ? F12 C17A F13A 88.7(9) . . ? F11 C17A F13 108.7(7) . . ? F12A C17A F13 82.6(7) . . ? F11A C17A F13 35.9(7) . . ? F12 C17A F13 101.9(6) . . ? F13A C17A F13 131.1(6) . . ? F11 C17A C16A 116.8(7) . . ? F12A C17A C16A 114.4(6) . . ? F11A C17A C16A 112.8(5) . . ? F12 C17A C16A 111.5(5) . . ? F13A C17A C16A 109.5(6) . . ? F13 C17A C16A 110.3(5) . . ? C13A C21A C16A 103.9(3) . . ? C13A C21A H21A 128.1 . . ? C16A C21A H21A 128.1 . . ? N1B C1B C4B 111.3(3) . . ? N1B C1B C3B 122.0(3) . . ? C4B C1B C3B 126.6(3) . . ? F1B C3B F3B 108.0(3) . . ? F1B C3B F2B 106.6(3) . . ? F3B C3B F2B 104.6(3) . . ? F1B C3B C1B 111.3(3) . . ? F3B C3B C1B 113.2(3) . . ? F2B C3B C1B 112.7(3) . . ? C1B C4B C5B 103.7(3) . . ? C1B C4B H4BA 128.1 . . ? C5B C4B H4BA 128.1 . . ? N6B C5B C4B 109.2(3) . . ? N6B C5B C7B 116.1(3) . . ? C4B C5B C7B 134.7(3) . . ? N8B C7B C12B 122.4(3) . . ? N8B C7B C5B 114.7(2) . . ? C12B C7B C5B 122.9(3) . . ? N8B C9B C10B 124.0(3) . . ? N8B C9B H9BA 118.0 . . ? C10B C9B H9BA 118.0 . . ? C11B C10B C9B 118.8(3) . . ? C11B C10B H10B 120.6 . . ? C9B C10B H10B 120.6 . . ? C12B C11B C10B 118.8(3) . . ? C12B C11B H11B 120.6 . . ? C10B C11B H11B 120.6 . . ? C11B C12B C7B 119.4(3) . . ? C11B C12B H12B 120.3 . . ? C7B C12B H12B 120.3 . . ? N1C C2C C4C 111.6(3) . . ? N1C C2C C3C 121.7(3) . . ? C4C C2C C3C 126.7(3) . . ? F2C C3C F1C 106.3(3) . . ? F2C C3C F3C 105.6(3) . . ? F1C C3C F3C 107.1(3) . . ? F2C C3C C2C 113.8(3) . . ? F1C C3C C2C 113.1(3) . . ? F3C C3C C2C 110.5(3) . . ? C2C C4C C5C 103.5(3) . . ? C2C C4C H4CA 128.3 . . ? C5C C4C H4CA 128.3 . . ? N6C C5C C4C 109.1(3) . . ? N6C C5C C7C 115.7(2) . . ? C4C C5C C7C 134.5(3) . . ? N8C C7C C12C 121.8(3) . . ? N8C C7C C5C 113.8(2) . . ? C12C C7C C5C 124.3(3) . . ? N8C C9C C10C 123.4(3) . . ? N8C C9C H9CA 118.3 . . ? C10C C9C H9CA 118.3 . . ? C9C C10C C11C 118.8(3) . . ? C9C C10C H10C 120.6 . . ? C11C C10C H10C 120.6 . . ? C12C C11C C10C 118.8(3) . . ? C12C C11C H11C 120.6 . . ? C10C C11C H11C 120.6 . . ? C11C C12C C7C 119.3(3) . . ? C11C C12C H12C 120.4 . . ? C7C C12C H12C 120.4 . . ? N1S C1S C2S 161(2) . . ? C1S C2S H2SA 109.5 . . ? C1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? C1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 62.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.407 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.055 data_cup _database_code_depnum_ccdc_archive 'CCDC 910212' #TrackingRef 'web_deposit_cif_file_0_GalinaRomanenko_1355844366.all(295-150-103)_last (1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H18 Cu2 F12 N12' _chemical_formula_weight 937.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1395(6) _cell_length_b 13.9368(9) _cell_length_c 14.3849(9) _cell_angle_alpha 76.2980(10) _cell_angle_beta 73.5830(10) _cell_angle_gamma 87.4360(10) _cell_volume 1707.08(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1751 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.66 _exptl_crystal_description box _exptl_crystal_colour green _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6625 _exptl_absorpt_correction_T_max 0.8990 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13349 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0984 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5898 _reflns_number_gt 4160 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+1.2138P] 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 5898 _refine_ls_number_parameters 588 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.982 _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 0.04359(7) 0.20347(5) 0.53224(4) 0.01538(19) Uani 1 1 d . . . Cu2 Cu -0.05324(7) 0.31256(5) 0.30605(5) 0.0194(2) Uani 1 1 d . . . N1AA N 0.0224(5) 0.2428(3) 0.1140(3) 0.0230(11) Uani 1 1 d . . . N1A N -0.0392(5) 0.3068(3) 0.1692(3) 0.0206(10) Uani 1 1 d . . . N8A N -0.1768(5) 0.4279(3) 0.2673(3) 0.0174(10) Uani 1 1 d . A . N14A N -0.1195(5) 0.3626(3) 0.4323(3) 0.0173(10) Uani 1 1 d . . . N15A N -0.0928(5) 0.3360(3) 0.5225(3) 0.0166(10) Uani 1 1 d . . . N1B N 0.1722(5) 0.2983(3) 0.3111(3) 0.0158(9) Uani 1 1 d . . . N6B N 0.1882(5) 0.2639(3) 0.4036(3) 0.0162(10) Uani 1 1 d . . . N8B N 0.2454(5) 0.2110(3) 0.5762(3) 0.0171(10) Uani 1 1 d . . . N1C N -0.1203(4) 0.1638(3) 0.3842(3) 0.0158(9) Uani 1 1 d . . . N6C N -0.0860(5) 0.1404(3) 0.4717(3) 0.0158(9) Uani 1 1 d . . . N8C N -0.0827(4) 0.1049(3) 0.6555(3) 0.0154(9) Uani 1 1 d . . . F1A F 0.0318(16) 0.2682(7) -0.1388(5) 0.047(3) Uani 0.60(3) 1 d PDU A 3 F2A F 0.1887(8) 0.1952(11) -0.0641(9) 0.047(3) Uani 0.60(3) 1 d PDU A 3 F3A F -0.0326(17) 0.1291(7) -0.0277(12) 0.049(3) Uani 0.60(3) 1 d PDU A 3 F1AA F 0.1833(14) 0.2228(17) -0.0969(18) 0.075(6) Uani 0.40(3) 1 d PDU A 4 F2AA F -0.050(3) 0.2419(16) -0.1129(16) 0.079(6) Uani 0.40(3) 1 d PDU A 4 F3AA F 0.003(3) 0.1195(7) -0.0101(15) 0.033(4) Uani 0.40(3) 1 d PDU A 4 F1B F 0.4720(4) 0.4285(3) 0.1070(2) 0.0517(11) Uani 1 1 d U . . F2B F 0.3467(4) 0.3111(3) 0.0903(2) 0.0399(9) Uani 1 1 d U . . F3B F 0.2315(4) 0.4413(2) 0.1231(2) 0.0396(9) Uani 1 1 d U . . F1C F -0.3151(4) 0.1853(2) 0.2602(2) 0.0336(8) Uani 1 1 d U . . F2C F -0.2010(4) 0.0524(2) 0.2357(2) 0.0321(8) Uani 1 1 d U . . F3C F -0.4220(4) 0.0441(3) 0.3404(2) 0.0370(9) Uani 1 1 d U . . F11 F -0.2705(15) 0.3313(11) 0.7457(9) 0.045(3) Uani 0.63(4) 1 d PDU B 1 F12 F -0.0298(12) 0.3456(12) 0.6914(11) 0.037(3) Uani 0.63(4) 1 d PDU B 1 F13 F -0.157(2) 0.4763(5) 0.7019(8) 0.046(3) Uani 0.63(4) 1 d PDU B 1 F11A F -0.230(5) 0.4626(18) 0.7180(15) 0.065(7) Uani 0.37(4) 1 d PDU B 2 F12A F -0.0221(15) 0.377(2) 0.6918(17) 0.043(5) Uani 0.37(4) 1 d PDU B 2 F13A F -0.241(3) 0.3075(16) 0.7368(15) 0.043(6) Uani 0.37(4) 1 d PDU B 2 C3A C -0.0145(6) 0.2752(4) 0.0282(4) 0.0230(13) Uani 1 1 d D A . C4A C 0.0381(6) 0.2160(4) -0.0499(4) 0.0368(14) Uani 1 1 d DU . . C5A C -0.0991(6) 0.3595(4) 0.0269(4) 0.0249(13) Uani 1 1 d . . . H5AA H -0.1386 0.3959 -0.0251 0.030 Uiso 1 1 calc R A . C6A C -0.1132(6) 0.3789(4) 0.1182(4) 0.0195(12) Uani 1 1 d . A . C7A C -0.1906(6) 0.4498(4) 0.1744(4) 0.0189(12) Uani 1 1 d . . . C10A C -0.3285(6) 0.5623(4) 0.3075(4) 0.0257(13) Uani 1 1 d . A . H10A H -0.3776 0.5996 0.3545 0.031 Uiso 1 1 calc R . . C11A C -0.3420(6) 0.5865(4) 0.2116(4) 0.0273(14) Uani 1 1 d . . . H11A H -0.4004 0.6419 0.1923 0.033 Uiso 1 1 calc R A . C12A C -0.2728(6) 0.5322(4) 0.1433(4) 0.0242(13) Uani 1 1 d . A . H12A H -0.2807 0.5502 0.0770 0.029 Uiso 1 1 calc R . . C9A C -0.2416(6) 0.4821(4) 0.3333(4) 0.0167(11) Uani 1 1 d . . . C13A C -0.2055(6) 0.4441(4) 0.4285(4) 0.0197(12) Uani 1 1 d . A . C16A C -0.1638(6) 0.4019(4) 0.5735(3) 0.0196(12) Uani 1 1 d D A . C17A C -0.1596(6) 0.3891(3) 0.6793(4) 0.0270(12) Uani 1 1 d DU . . C21A C -0.2370(6) 0.4723(4) 0.5182(4) 0.0194(12) Uani 1 1 d . . . H21A H -0.2945 0.5265 0.5371 0.023 Uiso 1 1 calc R A . C1B C 0.3108(6) 0.3346(4) 0.2525(4) 0.0189(12) Uani 1 1 d . . . C3B C 0.3392(6) 0.3788(4) 0.1441(4) 0.0266(13) Uani 1 1 d U . . C4B C 0.4163(6) 0.3235(4) 0.3060(4) 0.0201(12) Uani 1 1 d . . . H4BA H 0.5213 0.3424 0.2825 0.024 Uiso 1 1 calc R . . C5B C 0.3339(6) 0.2786(4) 0.4016(4) 0.0169(11) Uani 1 1 d . . . C7B C 0.3683(6) 0.2467(4) 0.4969(4) 0.0166(11) Uani 1 1 d . . . C9B C 0.2711(6) 0.1816(4) 0.6659(4) 0.0225(12) Uani 1 1 d . . . H9BA H 0.1866 0.1574 0.7219 0.027 Uiso 1 1 calc R . . C10B C 0.4133(6) 0.1842(4) 0.6820(4) 0.0254(13) Uani 1 1 d . . . H10B H 0.4257 0.1619 0.7470 0.031 Uiso 1 1 calc R . . C11B C 0.5364(6) 0.2199(4) 0.6011(4) 0.0242(13) Uani 1 1 d . . . H11B H 0.6353 0.2229 0.6096 0.029 Uiso 1 1 calc R . . C12B C 0.5141(6) 0.2515(4) 0.5073(4) 0.0221(12) Uani 1 1 d . . . H12B H 0.5977 0.2761 0.4508 0.026 Uiso 1 1 calc R . . C2C C -0.2210(6) 0.0922(4) 0.3895(4) 0.0183(12) Uani 1 1 d . . . C3C C -0.2877(6) 0.0944(4) 0.3061(4) 0.0223(12) Uani 1 1 d U . . C4C C -0.2517(6) 0.0245(4) 0.4798(4) 0.0179(12) Uani 1 1 d . . . H4CA H -0.3179 -0.0320 0.5025 0.021 Uiso 1 1 calc R . . C5C C -0.1625(6) 0.0584(4) 0.5299(4) 0.0162(11) Uani 1 1 d . . . C7C C -0.1530(5) 0.0342(4) 0.6322(4) 0.0157(11) Uani 1 1 d . . . C9C C -0.0885(6) 0.0946(4) 0.7516(4) 0.0217(12) Uani 1 1 d . . . H9CA H -0.0483 0.1468 0.7699 0.026 Uiso 1 1 calc R . . C10C C -0.1495(6) 0.0124(4) 0.8248(4) 0.0243(13) Uani 1 1 d . . . H10C H -0.1495 0.0079 0.8917 0.029 Uiso 1 1 calc R . . C11C C -0.2111(6) -0.0637(4) 0.8000(4) 0.0260(13) Uani 1 1 d . . . H11C H -0.2480 -0.1231 0.8484 0.031 Uiso 1 1 calc R . . C12C C -0.2175(6) -0.0509(4) 0.7030(4) 0.0195(12) Uani 1 1 d . . . H12C H -0.2655 -0.0998 0.6847 0.023 Uiso 1 1 calc R . . N1S N -0.4910(9) 0.1350(8) -0.0893(6) 0.105(3) Uani 1 1 d . . . C1S C -0.4479(9) 0.1311(9) -0.0229(7) 0.083(3) Uani 1 1 d . . . C2S C -0.3963(9) 0.1172(9) 0.0646(6) 0.101(4) Uani 1 1 d . . . H2SA H -0.3428 0.1773 0.0627 0.152 Uiso 1 1 calc R . . H2SB H -0.3268 0.0616 0.0670 0.152 Uiso 1 1 calc R . . H2SC H -0.4842 0.1031 0.1241 0.152 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 0.0158(3) 0.0174(4) 0.0143(3) -0.0047(3) -0.0054(3) -0.0004(3) Cu2 0.0241(4) 0.0218(4) 0.0165(4) -0.0085(3) -0.0104(3) 0.0099(3) N1AA 0.027(3) 0.026(3) 0.019(2) -0.010(2) -0.008(2) 0.010(2) N1A 0.023(2) 0.024(3) 0.017(2) -0.008(2) -0.010(2) 0.008(2) N8A 0.018(2) 0.015(2) 0.021(2) -0.005(2) -0.0097(19) 0.0022(19) N14A 0.019(2) 0.014(2) 0.022(2) -0.0098(19) -0.010(2) 0.010(2) N15A 0.017(2) 0.022(2) 0.014(2) -0.0085(19) -0.0058(18) 0.006(2) N1B 0.019(2) 0.017(2) 0.012(2) -0.0032(18) -0.0047(18) 0.0009(19) N6B 0.018(2) 0.015(2) 0.017(2) -0.0060(19) -0.0065(19) 0.0026(19) N8B 0.021(2) 0.017(2) 0.015(2) -0.0043(19) -0.007(2) -0.001(2) N1C 0.015(2) 0.018(2) 0.018(2) -0.0083(19) -0.0074(18) 0.0063(19) N6C 0.016(2) 0.019(2) 0.014(2) -0.0063(19) -0.0045(18) 0.0034(19) N8C 0.014(2) 0.016(2) 0.018(2) -0.0074(19) -0.0057(18) 0.0063(19) F1A 0.075(7) 0.050(5) 0.018(3) -0.010(3) -0.012(4) 0.006(5) F2A 0.049(4) 0.062(7) 0.032(5) -0.023(5) -0.007(3) 0.018(4) F3A 0.057(7) 0.050(5) 0.055(7) -0.034(4) -0.023(5) -0.003(4) F1AA 0.088(6) 0.056(10) 0.049(11) -0.028(9) 0.046(7) -0.026(7) F2AA 0.159(13) 0.069(10) 0.044(9) -0.037(7) -0.072(9) 0.057(10) F3AA 0.051(10) 0.028(5) 0.037(7) -0.019(4) -0.028(6) 0.001(5) F1B 0.046(2) 0.075(3) 0.0252(19) 0.0110(19) -0.0083(17) -0.037(2) F2B 0.054(2) 0.044(2) 0.0235(18) -0.0153(16) -0.0070(17) 0.0003(18) F3B 0.056(2) 0.036(2) 0.0255(19) -0.0010(16) -0.0170(17) 0.0142(18) F1C 0.042(2) 0.0277(18) 0.044(2) -0.0118(16) -0.0319(17) 0.0125(16) F2C 0.0347(19) 0.039(2) 0.0318(19) -0.0216(16) -0.0134(15) 0.0090(16) F3C 0.0241(17) 0.053(2) 0.040(2) -0.0164(18) -0.0131(16) -0.0086(17) F11 0.045(5) 0.062(6) 0.022(4) -0.013(4) 0.003(4) -0.010(5) F12 0.049(4) 0.039(6) 0.035(5) -0.018(5) -0.023(4) 0.008(4) F13 0.076(7) 0.032(3) 0.040(4) -0.025(3) -0.019(4) 0.000(4) F11A 0.129(15) 0.050(8) 0.035(8) -0.035(7) -0.042(9) 0.050(9) F12A 0.042(6) 0.061(13) 0.028(8) 0.002(8) -0.019(6) -0.033(6) F13A 0.052(10) 0.045(8) 0.023(8) -0.012(6) 0.009(6) -0.009(8) C3A 0.031(3) 0.023(3) 0.015(3) -0.003(2) -0.009(2) 0.001(3) C4A 0.055(3) 0.033(3) 0.029(3) -0.011(3) -0.019(3) 0.008(3) C5A 0.031(3) 0.026(3) 0.020(3) -0.002(3) -0.014(3) 0.000(3) C6A 0.016(3) 0.022(3) 0.021(3) -0.002(2) -0.007(2) -0.001(2) C7A 0.017(3) 0.020(3) 0.023(3) -0.005(2) -0.010(2) 0.002(2) C10A 0.028(3) 0.021(3) 0.033(3) -0.013(3) -0.012(3) 0.006(3) C11A 0.031(3) 0.017(3) 0.036(4) -0.003(3) -0.015(3) 0.007(3) C12A 0.028(3) 0.022(3) 0.025(3) 0.000(3) -0.015(3) 0.001(3) C9A 0.015(3) 0.015(3) 0.022(3) -0.006(2) -0.006(2) 0.001(2) C13A 0.021(3) 0.018(3) 0.019(3) -0.004(2) -0.004(2) -0.004(2) C16A 0.019(3) 0.020(3) 0.021(3) -0.008(2) -0.006(2) 0.002(2) C17A 0.035(3) 0.025(3) 0.026(3) -0.014(2) -0.010(3) 0.004(2) C21A 0.018(3) 0.016(3) 0.025(3) -0.010(2) -0.003(2) 0.005(2) C1B 0.023(3) 0.016(3) 0.019(3) -0.005(2) -0.006(2) 0.000(2) C3B 0.025(3) 0.033(3) 0.020(3) -0.004(2) -0.003(2) -0.005(2) C4B 0.014(3) 0.020(3) 0.025(3) -0.005(2) -0.003(2) -0.001(2) C5B 0.016(3) 0.014(3) 0.022(3) -0.007(2) -0.007(2) 0.002(2) C7B 0.020(3) 0.010(3) 0.022(3) -0.008(2) -0.007(2) 0.003(2) C9B 0.024(3) 0.024(3) 0.021(3) -0.005(2) -0.008(2) -0.001(3) C10B 0.038(4) 0.017(3) 0.028(3) -0.006(3) -0.019(3) 0.002(3) C11B 0.023(3) 0.022(3) 0.036(3) -0.016(3) -0.015(3) 0.006(3) C12B 0.016(3) 0.023(3) 0.027(3) -0.008(3) -0.003(2) 0.000(2) C2C 0.013(3) 0.018(3) 0.028(3) -0.014(2) -0.006(2) 0.006(2) C3C 0.018(3) 0.025(3) 0.027(3) -0.010(2) -0.007(2) 0.003(2) C4C 0.015(3) 0.011(3) 0.027(3) -0.007(2) -0.005(2) 0.001(2) C5C 0.015(3) 0.015(3) 0.018(3) -0.006(2) -0.003(2) 0.005(2) C7C 0.010(3) 0.015(3) 0.024(3) -0.010(2) -0.004(2) 0.009(2) C9C 0.017(3) 0.027(3) 0.021(3) -0.008(3) -0.006(2) 0.003(2) C10C 0.021(3) 0.032(3) 0.017(3) -0.003(3) -0.004(2) 0.004(3) C11C 0.021(3) 0.022(3) 0.029(3) -0.001(3) -0.004(3) 0.006(3) C12C 0.018(3) 0.015(3) 0.023(3) -0.005(2) 0.000(2) 0.001(2) N1S 0.087(6) 0.178(10) 0.067(5) -0.044(6) -0.042(5) 0.055(6) C1S 0.050(5) 0.154(10) 0.047(5) -0.029(6) -0.015(4) 0.031(6) C2S 0.038(5) 0.215(13) 0.055(6) -0.040(7) -0.017(4) 0.021(6) _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 N6B 1.964(4) . ? Cu1 N6C 1.994(4) . ? Cu1 N8C 2.049(4) . ? Cu1 N8B 2.127(4) . ? Cu1 N15A 2.181(4) . ? Cu2 N1A 1.956(4) . ? Cu2 N8A 1.984(4) . ? Cu2 N14A 2.023(4) . ? Cu2 N1B 2.082(4) . ? Cu2 N1C 2.135(4) . ? N1AA N1A 1.335(6) . ? N1AA C3A 1.340(7) . ? N1A C6A 1.370(6) . ? N8A C7A 1.340(6) . ? N8A C9A 1.343(6) . ? N14A N15A 1.349(5) . ? N14A C13A 1.352(7) . ? N15A C16A 1.342(6) . ? N1B N6B 1.350(5) . ? N1B C1B 1.351(6) . ? N6B C5B 1.348(6) . ? N8B C9B 1.341(6) . ? N8B C7B 1.367(6) . ? N1C N6C 1.344(5) . ? N1C C2C 1.362(6) . ? N6C C5C 1.335(6) . ? N8C C9C 1.341(6) . ? N8C C7C 1.353(6) . ? F1A C4A 1.329(7) . ? F2A C4A 1.361(8) . ? F3A C4A 1.325(8) . ? F1AA C4A 1.304(9) . ? F2AA C4A 1.352(9) . ? F3AA C4A 1.346(9) . ? F1B C3B 1.331(6) . ? F2B C3B 1.342(6) . ? F3B C3B 1.336(7) . ? F1C C3C 1.332(6) . ? F2C C3C 1.334(6) . ? F3C C3C 1.346(6) . ? F11 C17A 1.323(8) . ? F12 C17A 1.344(7) . ? F13 C17A 1.332(7) . ? F11A C17A 1.335(8) . ? F12A C17A 1.317(9) . ? F13A C17A 1.347(9) . ? C3A C5A 1.377(7) . ? C3A C4A 1.507(6) . ? C5A C6A 1.372(7) . ? C5A H5AA 0.9500 . ? C6A C7A 1.457(7) . ? C7A C12A 1.397(7) . ? C10A C11A 1.380(8) . ? C10A C9A 1.381(7) . ? C10A H10A 0.9500 . ? C11A C12A 1.377(8) . ? C11A H11A 0.9500 . ? C12A H12A 0.9500 . ? C9A C13A 1.471(7) . ? C13A C21A 1.387(7) . ? C16A C21A 1.383(7) . ? C16A C17A 1.502(6) . ? C21A H21A 0.9500 . ? C1B C4B 1.377(7) . ? C1B C3B 1.486(7) . ? C4B C5B 1.378(7) . ? C4B H4BA 0.9500 . ? C5B C7B 1.454(7) . ? C7B C12B 1.389(7) . ? C9B C10B 1.387(7) . ? C9B H9BA 0.9500 . ? C10B C11B 1.379(8) . ? C10B H10B 0.9500 . ? C11B C12B 1.386(8) . ? C11B H11B 0.9500 . ? C12B H12B 0.9500 . ? C2C C4C 1.376(7) . ? C2C C3C 1.485(7) . ? C4C C5C 1.391(7) . ? C4C H4CA 0.9500 . ? C5C C7C 1.456(7) . ? C7C C12C 1.394(7) . ? C9C C10C 1.373(7) . ? C9C H9CA 0.9500 . ? C10C C11C 1.384(8) . ? C10C H10C 0.9500 . ? C11C C12C 1.382(7) . ? C11C H11C 0.9500 . ? C12C H12C 0.9500 . ? N1S C1S 1.120(10) . ? C1S C2S 1.435(11) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6B Cu1 N6C 94.15(16) . . ? N6B Cu1 N8C 163.92(16) . . ? N6C Cu1 N8C 79.38(16) . . ? N6B Cu1 N8B 79.20(16) . . ? N6C Cu1 N8B 151.52(16) . . ? N8C Cu1 N8B 99.42(16) . . ? N6B Cu1 N15A 90.12(16) . . ? N6C Cu1 N15A 90.94(16) . . ? N8C Cu1 N15A 104.58(16) . . ? N8B Cu1 N15A 116.51(15) . . ? N1A Cu2 N8A 79.53(17) . . ? N1A Cu2 N14A 157.61(17) . . ? N8A Cu2 N14A 78.10(17) . . ? N1A Cu2 N1B 103.12(17) . . ? N8A Cu2 N1B 133.12(16) . . ? N14A Cu2 N1B 92.89(16) . . ? N1A Cu2 N1C 101.13(17) . . ? N8A Cu2 N1C 130.77(16) . . ? N14A Cu2 N1C 92.77(16) . . ? N1B Cu2 N1C 95.17(15) . . ? N1A N1AA C3A 105.2(4) . . ? N1AA N1A C6A 110.5(4) . . ? N1AA N1A Cu2 133.3(3) . . ? C6A N1A Cu2 116.1(3) . . ? C7A N8A C9A 122.1(4) . . ? C7A N8A Cu2 118.1(3) . . ? C9A N8A Cu2 119.8(3) . . ? N15A N14A C13A 109.1(4) . . ? N15A N14A Cu2 134.9(3) . . ? C13A N14A Cu2 116.0(3) . . ? C16A N15A N14A 106.2(4) . . ? C16A N15A Cu1 143.6(3) . . ? N14A N15A Cu1 110.2(3) . . ? N6B N1B C1B 106.2(4) . . ? N6B N1B Cu2 114.3(3) . . ? C1B N1B Cu2 137.3(3) . . ? C5B N6B N1B 109.2(4) . . ? C5B N6B Cu1 118.0(3) . . ? N1B N6B Cu1 132.7(3) . . ? C9B N8B C7B 117.0(4) . . ? C9B N8B Cu1 130.7(4) . . ? C7B N8B Cu1 112.2(3) . . ? N6C N1C C2C 105.6(4) . . ? N6C N1C Cu2 111.6(3) . . ? C2C N1C Cu2 139.9(3) . . ? C5C N6C N1C 110.3(4) . . ? C5C N6C Cu1 115.4(3) . . ? N1C N6C Cu1 134.2(3) . . ? C9C N8C C7C 117.6(4) . . ? C9C N8C Cu1 129.1(4) . . ? C7C N8C Cu1 112.8(3) . . ? N1AA C3A C5A 112.5(4) . . ? N1AA C3A C4A 117.5(4) . . ? C5A C3A C4A 129.9(5) . . ? F1AA C4A F3A 118.2(13) . . ? F1AA C4A F1A 80.5(11) . . ? F3A C4A F1A 110.5(7) . . ? F1AA C4A F3AA 107.1(11) . . ? F3A C4A F3AA 19.9(10) . . ? F1A C4A F3AA 127.3(10) . . ? F1AA C4A F2AA 112.2(10) . . ? F3A C4A F2AA 83.4(10) . . ? F1A C4A F2AA 34.5(11) . . ? F3AA C4A F2AA 103.1(10) . . ? F1AA C4A F2A 23.5(11) . . ? F3A C4A F2A 105.1(8) . . ? F1A C4A F2A 103.6(6) . . ? F3AA C4A F2A 89.4(11) . . ? F2AA C4A F2A 132.9(12) . . ? F1AA C4A C3A 116.2(10) . . ? F3A C4A C3A 114.8(8) . . ? F1A C4A C3A 111.4(6) . . ? F3AA C4A C3A 110.9(10) . . ? F2AA C4A C3A 106.7(7) . . ? F2A C4A C3A 110.7(6) . . ? C6A C5A C3A 103.9(5) . . ? C6A C5A H5AA 128.1 . . ? C3A C5A H5AA 128.1 . . ? N1A C6A C5A 107.9(5) . . ? N1A C6A C7A 114.6(4) . . ? C5A C6A C7A 137.4(5) . . ? N8A C7A C12A 119.8(5) . . ? N8A C7A C6A 111.6(4) . . ? C12A C7A C6A 128.6(5) . . ? C11A C10A C9A 118.1(5) . . ? C11A C10A H10A 121.0 . . ? C9A C10A H10A 121.0 . . ? C12A C11A C10A 121.4(5) . . ? C12A C11A H11A 119.3 . . ? C10A C11A H11A 119.3 . . ? C11A C12A C7A 118.1(5) . . ? C11A C12A H12A 121.0 . . ? C7A C12A H12A 121.0 . . ? N8A C9A C10A 120.4(5) . . ? N8A C9A C13A 111.2(4) . . ? C10A C9A C13A 128.3(5) . . ? N14A C13A C21A 109.8(5) . . ? N14A C13A C9A 114.8(4) . . ? C21A C13A C9A 135.4(5) . . ? N15A C16A C21A 112.2(4) . . ? N15A C16A C17A 118.6(4) . . ? C21A C16A C17A 129.2(5) . . ? F12A C17A F11 116.9(15) . . ? F12A C17A F13 86.7(12) . . ? F11 C17A F13 110.7(7) . . ? F12A C17A F11A 111.3(11) . . ? F11 C17A F11A 85.8(15) . . ? F13 C17A F11A 28.8(14) . . ? F12A C17A F12 19.3(14) . . ? F11 C17A F12 105.1(8) . . ? F13 C17A F12 105.5(7) . . ? F11A C17A F12 128.0(13) . . ? F12A C17A F13A 105.7(11) . . ? F11 C17A F13A 18.8(15) . . ? F13 C17A F13A 127.2(12) . . ? F11A C17A F13A 104.2(11) . . ? F12 C17A F13A 90.5(15) . . ? F12A C17A C16A 114.3(11) . . ? F11 C17A C16A 114.0(8) . . ? F13 C17A C16A 111.0(6) . . ? F11A C17A C16A 111.0(8) . . ? F12 C17A C16A 110.0(7) . . ? F13A C17A C16A 109.6(11) . . ? C16A C21A C13A 102.8(4) . . ? C16A C21A H21A 128.6 . . ? C13A C21A H21A 128.6 . . ? N1B C1B C4B 111.3(4) . . ? N1B C1B C3B 122.1(5) . . ? C4B C1B C3B 126.6(5) . . ? F1B C3B F3B 107.3(5) . . ? F1B C3B F2B 105.9(5) . . ? F3B C3B F2B 106.0(4) . . ? F1B C3B C1B 110.9(4) . . ? F3B C3B C1B 113.2(5) . . ? F2B C3B C1B 113.1(5) . . ? C1B C4B C5B 103.9(4) . . ? C1B C4B H4BA 128.0 . . ? C5B C4B H4BA 128.0 . . ? N6B C5B C4B 109.5(4) . . ? N6B C5B C7B 115.6(4) . . ? C4B C5B C7B 134.9(5) . . ? N8B C7B C12B 122.1(5) . . ? N8B C7B C5B 114.8(4) . . ? C12B C7B C5B 123.2(5) . . ? N8B C9B C10B 124.1(5) . . ? N8B C9B H9BA 117.9 . . ? C10B C9B H9BA 117.9 . . ? C11B C10B C9B 118.2(5) . . ? C11B C10B H10B 120.9 . . ? C9B C10B H10B 120.9 . . ? C10B C11B C12B 119.3(5) . . ? C10B C11B H11B 120.3 . . ? C12B C11B H11B 120.3 . . ? C11B C12B C7B 119.3(5) . . ? C11B C12B H12B 120.4 . . ? C7B C12B H12B 120.4 . . ? N1C C2C C4C 111.4(4) . . ? N1C C2C C3C 121.2(5) . . ? C4C C2C C3C 127.4(5) . . ? F2C C3C F1C 106.6(4) . . ? F2C C3C F3C 105.9(4) . . ? F1C C3C F3C 106.7(4) . . ? F2C C3C C2C 113.7(4) . . ? F1C C3C C2C 113.3(4) . . ? F3C C3C C2C 110.1(4) . . ? C2C C4C C5C 103.5(4) . . ? C2C C4C H4CA 128.2 . . ? C5C C4C H4CA 128.2 . . ? N6C C5C C4C 109.3(4) . . ? N6C C5C C7C 115.2(4) . . ? C4C C5C C7C 134.7(5) . . ? N8C C7C C12C 121.7(5) . . ? N8C C7C C5C 114.1(4) . . ? C12C C7C C5C 124.1(5) . . ? N8C C9C C10C 123.3(5) . . ? N8C C9C H9CA 118.4 . . ? C10C C9C H9CA 118.4 . . ? C9C C10C C11C 119.3(5) . . ? C9C C10C H10C 120.3 . . ? C11C C10C H10C 120.3 . . ? C12C C11C C10C 118.2(5) . . ? C12C C11C H11C 120.9 . . ? C10C C11C H11C 120.9 . . ? C11C C12C C7C 119.5(5) . . ? C11C C12C H12C 120.2 . . ? C7C C12C H12C 120.2 . . ? N1S C1S C2S 175.1(14) . . ? C1S C2S H2SA 109.5 . . ? C1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? C1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.627 _refine_diff_density_min -0.731 _refine_diff_density_rms 0.149