# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Robert Singer' 'Gregory McManus' 'Prashant U Naik' 'Michael J Zaworotko' _publ_contact_author_name 'Robert Singer' _publ_contact_author_email ROBERT.SINGER@SMU.CA _publ_section_title ; Ionic complexes for biphasic catalysis and metal extractions ; # Attachment 'Compound_4.cif' data_rs0101 _database_code_depnum_ccdc_archive 'CCDC 693564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 Cu F12 N6 O4 P2' _chemical_formula_weight 815.99 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 10.115(4) _cell_length_b 18.066(7) _cell_length_c 18.153(6) _cell_angle_alpha 70.115(8) _cell_angle_beta 85.613(8) _cell_angle_gamma 74.682(7) _cell_volume 3008.5(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour gold _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1644 _exptl_absorpt_coefficient_mu 0.952 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17825 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.1654 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.19 _diffrn_reflns_theta_max 28.31 _reflns_number_total 13069 _reflns_number_gt 6853 _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^)+(0.0724P)^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 13069 _refine_ls_number_parameters 891 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1575 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2037 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 0.76948(8) 0.86827(4) 0.50293(4) 0.0157(2) Uani 1 1 d . . . Cu2 Cu 0.29918(8) 0.61481(4) 0.48516(4) 0.0165(2) Uani 1 1 d . . . N11 N 0.9283(5) 0.8954(3) 0.4438(3) 0.0192(12) Uani 1 1 d . . . N12 N 1.1321(5) 0.7068(3) 0.1903(3) 0.0162(11) Uani 1 1 d . . . N13 N 1.1337(5) 0.7981(3) 0.0772(3) 0.0206(12) Uani 1 1 d . . . O11 O 0.7900(4) 0.7755(2) 0.4725(2) 0.0170(9) Uani 1 1 d . . . O12 O 0.9626(5) 0.9656(3) 0.4442(2) 0.0227(10) Uani 1 1 d . . . H12 H 0.9160 0.9830 0.4780 0.034 Uiso 1 1 calc R . . C11 C 1.0072(6) 0.8581(4) 0.4012(3) 0.0177(14) Uani 1 1 d . . . H11 H 1.0804 0.8798 0.3748 0.021 Uiso 1 1 calc R . . C12 C 0.9903(6) 0.7859(4) 0.3918(3) 0.0183(14) Uani 1 1 d . . . C13 C 0.8832(6) 0.7472(4) 0.4265(3) 0.0164(14) Uani 1 1 d . . . C14 C 0.8772(7) 0.6780(4) 0.4104(3) 0.0190(14) Uani 1 1 d . . . H14 H 0.8071 0.6516 0.4334 0.023 Uiso 1 1 calc R . . C15 C 0.9702(7) 0.6466(4) 0.3622(3) 0.0201(15) Uani 1 1 d . . . H15 H 0.9627 0.5996 0.3521 0.024 Uiso 1 1 calc R . . C16 C 1.0754(6) 0.6835(4) 0.3281(3) 0.0159(13) Uani 1 1 d . . . C17 C 1.0840(6) 0.7513(4) 0.3436(3) 0.0158(13) Uani 1 1 d . . . H17 H 1.1561 0.7761 0.3209 0.019 Uiso 1 1 calc R . . C18 C 1.1716(7) 0.6523(4) 0.2711(3) 0.0211(15) Uani 1 1 d . . . H18A H 1.2669 0.6503 0.2824 0.025 Uiso 1 1 calc R . . H18B H 1.1670 0.5965 0.2770 0.025 Uiso 1 1 calc R . . C19 C 1.2048(7) 0.7550(4) 0.1429(4) 0.0220(15) Uani 1 1 d . . . H19 H 1.2930 0.7580 0.1544 0.026 Uiso 1 1 calc R . . C20 C 1.0099(6) 0.7204(4) 0.1537(4) 0.0215(15) Uani 1 1 d . . . H20 H 0.9386 0.6942 0.1743 0.026 Uiso 1 1 calc R . . C21 C 1.0099(7) 0.7780(4) 0.0830(4) 0.0213(15) Uani 1 1 d . . . H21 H 0.9384 0.8004 0.0447 0.026 Uiso 1 1 calc R . . C22 C 1.1794(7) 0.8586(4) 0.0107(4) 0.0328(18) Uani 1 1 d . . . H22A H 1.2691 0.8629 0.0232 0.049 Uiso 1 1 calc R . . H22B H 1.1129 0.9116 0.0002 0.049 Uiso 1 1 calc R . . H22C H 1.1869 0.8418 -0.0357 0.049 Uiso 1 1 calc R . . N31 N 0.6042(5) 0.8458(3) 0.5561(3) 0.0167(12) Uani 1 1 d . . . N32 N 0.3501(5) 1.0653(3) 0.7878(3) 0.0168(11) Uani 1 1 d . . . N33 N 0.4296(5) 0.9846(3) 0.9021(3) 0.0205(12) Uani 1 1 d . . . O31 O 0.7530(4) 0.9588(3) 0.5359(2) 0.0204(10) Uani 1 1 d . . . O32 O 0.5657(4) 0.7774(3) 0.5551(2) 0.0204(10) Uani 1 1 d . . . H32 H 0.6179 0.7561 0.5255 0.031 Uiso 1 1 calc R . . C31 C 0.5188(7) 0.8882(4) 0.5922(3) 0.0200(14) Uani 1 1 d . . . H31 H 0.4387 0.8709 0.6130 0.024 Uiso 1 1 calc R . . C32 C 0.5378(6) 0.9602(4) 0.6026(3) 0.0170(14) Uani 1 1 d . . . C33 C 0.6536(6) 0.9918(4) 0.5760(3) 0.0175(14) Uani 1 1 d . . . C34 C 0.6639(7) 1.0597(4) 0.5935(3) 0.0209(15) Uani 1 1 d . . . H34 H 0.7422 1.0805 0.5770 0.025 Uiso 1 1 calc R . . C35 C 0.5639(6) 1.0970(4) 0.6338(3) 0.0202(14) Uani 1 1 d . . . H35 H 0.5752 1.1424 0.6455 0.024 Uiso 1 1 calc R . . C36 C 0.4463(6) 1.0698(4) 0.6580(3) 0.0176(14) Uani 1 1 d . . . C37 C 0.4360(7) 1.0003(4) 0.6434(3) 0.0203(15) Uani 1 1 d . . . H37 H 0.3581 0.9795 0.6614 0.024 Uiso 1 1 calc R . . C38 C 0.3385(7) 1.1097(4) 0.7035(3) 0.0266(16) Uani 1 1 d . . . H38A H 0.3461 1.1657 0.6938 0.032 Uiso 1 1 calc R . . H38B H 0.2469 1.1135 0.6846 0.032 Uiso 1 1 calc R . . C39 C 0.4596(7) 1.0107(4) 0.8276(3) 0.0185(14) Uani 1 1 d . . . H39 H 0.5455 0.9934 0.8054 0.022 Uiso 1 1 calc R . . C40 C 0.2458(7) 1.0742(4) 0.8401(4) 0.0248(16) Uani 1 1 d . . . H40 H 0.1564 1.1095 0.8287 0.030 Uiso 1 1 calc R . . C41 C 0.2973(7) 1.0222(4) 0.9110(4) 0.0277(17) Uani 1 1 d . . . H41 H 0.2489 1.0134 0.9589 0.033 Uiso 1 1 calc R . . C42 C 0.5197(7) 0.9177(4) 0.9616(4) 0.0302(17) Uani 1 1 d . . . H42A H 0.5178 0.8658 0.9562 0.045 Uiso 1 1 calc R . . H42B H 0.4882 0.9183 1.0139 0.045 Uiso 1 1 calc R . . H42C H 0.6136 0.9241 0.9547 0.045 Uiso 1 1 calc R . . N51 N 0.1390(5) 0.5885(3) 0.5427(3) 0.0175(12) Uani 1 1 d . . . N52 N -0.0750(5) 0.7903(3) 0.7930(3) 0.0173(12) Uani 1 1 d . . . N53 N -0.0882(5) 0.7158(3) 0.9134(3) 0.0172(12) Uani 1 1 d . . . O51 O 0.2798(4) 0.7061(2) 0.5177(2) 0.0196(10) Uani 1 1 d . . . O52 O 0.1014(5) 0.5202(3) 0.5415(2) 0.0258(11) Uani 1 1 d . . . H52 H 0.1360 0.5077 0.5024 0.039 Uiso 1 1 calc R . . C51 C 0.0581(6) 0.6279(4) 0.5828(3) 0.0169(14) Uani 1 1 d . . . H51 H -0.0191 0.6085 0.6059 0.020 Uiso 1 1 calc R . . C52 C 0.0766(6) 0.6989(4) 0.5950(3) 0.0154(13) Uani 1 1 d . . . C53 C 0.1870(6) 0.7341(4) 0.5637(3) 0.0173(14) Uani 1 1 d . . . C54 C 0.1970(7) 0.8019(4) 0.5823(4) 0.0223(15) Uani 1 1 d . . . H54 H 0.2720 0.8252 0.5630 0.027 Uiso 1 1 calc R . . C55 C 0.1018(7) 0.8353(4) 0.6276(3) 0.0204(15) Uani 1 1 d . . . H55 H 0.1115 0.8812 0.6388 0.024 Uiso 1 1 calc R . . C56 C -0.0103(6) 0.8023(4) 0.6575(3) 0.0180(14) Uani 1 1 d . . . C57 C -0.0204(6) 0.7351(4) 0.6414(3) 0.0199(14) Uani 1 1 d . . . H57 H -0.0950 0.7119 0.6622 0.024 Uiso 1 1 calc R . . C58 C -0.1116(7) 0.8378(4) 0.7098(3) 0.0262(16) Uani 1 1 d . . . H58A H -0.1110 0.8952 0.6992 0.031 Uiso 1 1 calc R . . H58B H -0.2051 0.8366 0.6986 0.031 Uiso 1 1 calc R . . C59 C -0.1553(7) 0.7547(4) 0.8454(4) 0.0202(14) Uani 1 1 d . . . H59 H -0.2474 0.7565 0.8361 0.024 Uiso 1 1 calc R . . C60 C 0.0503(7) 0.7742(4) 0.8281(4) 0.0239(15) Uani 1 1 d . . . H60 H 0.1281 0.7922 0.8040 0.029 Uiso 1 1 calc R . . C61 C 0.0413(7) 0.7282(4) 0.9030(4) 0.0237(15) Uani 1 1 d . . . H61 H 0.1118 0.7078 0.9419 0.028 Uiso 1 1 calc R . . C62 C -0.1425(7) 0.6652(4) 0.9842(3) 0.0282(17) Uani 1 1 d . . . H62A H -0.2428 0.6837 0.9832 0.042 Uiso 1 1 calc R . . H62B H -0.1062 0.6698 1.0306 0.042 Uiso 1 1 calc R . . H62C H -0.1149 0.6084 0.9861 0.042 Uiso 1 1 calc R . . N71 N 0.4627(6) 0.6410(3) 0.4310(3) 0.0198(12) Uani 1 1 d . . . N72 N 0.6497(6) 0.4706(3) 0.1607(3) 0.0238(13) Uani 1 1 d . . . N73 N 0.5148(5) 0.5560(3) 0.0654(3) 0.0206(12) Uani 1 1 d . . . O71 O 0.3154(4) 0.5261(2) 0.4482(2) 0.0201(10) Uani 1 1 d . . . O72 O 0.5047(5) 0.7053(3) 0.4395(2) 0.0220(10) Uani 1 1 d . . . H72 H 0.4503 0.7257 0.4688 0.033 Uiso 1 1 calc R . . C71 C 0.5426(6) 0.6041(4) 0.3897(3) 0.0179(14) Uani 1 1 d . . . H71 H 0.6212 0.6230 0.3687 0.021 Uiso 1 1 calc R . . C72 C 0.5214(6) 0.5351(4) 0.3724(3) 0.0176(14) Uani 1 1 d . . . C73 C 0.4103(6) 0.4996(4) 0.4025(3) 0.0170(14) Uani 1 1 d . . . C74 C 0.4027(7) 0.4335(4) 0.3797(4) 0.0215(15) Uani 1 1 d . . . H74 H 0.3299 0.4082 0.3989 0.026 Uiso 1 1 calc R . . C75 C 0.4959(7) 0.4042(4) 0.3311(3) 0.0209(15) Uani 1 1 d . . . H75 H 0.4864 0.3594 0.3176 0.025 Uiso 1 1 calc R . . C76 C 0.6047(7) 0.4393(4) 0.3009(3) 0.0197(14) Uani 1 1 d . . . C77 C 0.6153(6) 0.5040(4) 0.3229(3) 0.0185(14) Uani 1 1 d . . . H77 H 0.6894 0.5281 0.3036 0.022 Uiso 1 1 calc R . . C78 C 0.6999(7) 0.4149(4) 0.2404(4) 0.0267(16) Uani 1 1 d . . . H78A H 0.7935 0.4177 0.2493 0.032 Uiso 1 1 calc R . . H78B H 0.7036 0.3582 0.2451 0.032 Uiso 1 1 calc R . . C79 C 0.5217(7) 0.5137(4) 0.1418(4) 0.0215(15) Uani 1 1 d . . . H79 H 0.4471 0.5144 0.1769 0.026 Uiso 1 1 calc R . . C80 C 0.7272(7) 0.4840(4) 0.0936(4) 0.0250(16) Uani 1 1 d . . . H80 H 0.8216 0.4595 0.0893 0.030 Uiso 1 1 calc R . . C81 C 0.6411(7) 0.5391(4) 0.0351(4) 0.0272(17) Uani 1 1 d . . . H81 H 0.6654 0.5618 -0.0179 0.033 Uiso 1 1 calc R . . C82 C 0.3926(7) 0.6177(4) 0.0248(4) 0.0291(17) Uani 1 1 d . . . H82A H 0.3100 0.6029 0.0504 0.044 Uiso 1 1 calc R . . H82B H 0.3922 0.6204 -0.0300 0.044 Uiso 1 1 calc R . . H82C H 0.3943 0.6709 0.0270 0.044 Uiso 1 1 calc R . . P101 P 0.60495(18) 0.73131(10) 0.15614(10) 0.0203(4) Uani 1 1 d . . . F101 F 0.5149(4) 0.8171(2) 0.1576(2) 0.0445(11) Uani 1 1 d . . . F102 F 0.6944(4) 0.7230(3) 0.2280(2) 0.0444(12) Uani 1 1 d . . . F103 F 0.6940(5) 0.6460(2) 0.1531(2) 0.0448(12) Uani 1 1 d . . . F104 F 0.5132(4) 0.7405(3) 0.0836(2) 0.0402(11) Uani 1 1 d . . . F105 F 0.5011(4) 0.6873(2) 0.2154(2) 0.0343(10) Uani 1 1 d . . . F106 F 0.7061(4) 0.7757(2) 0.0959(2) 0.0304(10) Uani 1 1 d . . . P201 P 0.11946(19) 0.47242(11) 0.17305(11) 0.0254(4) Uani 1 1 d . . . F201 F -0.0178(5) 0.5316(3) 0.1876(3) 0.0740(17) Uani 1 1 d . . . F202 F 0.2027(4) 0.5377(3) 0.1703(2) 0.0441(12) Uani 1 1 d . . . F203 F 0.2550(4) 0.4159(2) 0.1538(2) 0.0453(12) Uani 1 1 d . . . F204 F 0.0357(4) 0.4074(3) 0.1761(3) 0.0469(12) Uani 1 1 d . . . F205 F 0.1504(5) 0.4313(3) 0.2633(2) 0.0610(15) Uani 1 1 d . . . F206 F 0.0903(5) 0.5141(3) 0.0809(3) 0.0654(15) Uani 1 1 d . . . P301 P 0.1350(2) 0.99736(12) 0.15771(11) 0.0274(4) Uani 1 1 d . . . F301 F 0.2678(4) 0.9613(2) 0.1146(2) 0.0352(10) Uani 1 1 d . . . F302 F 0.2236(4) 1.0374(3) 0.1942(3) 0.0556(14) Uani 1 1 d . . . F303 F 0.0029(5) 1.0348(3) 0.1990(3) 0.0622(15) Uani 1 1 d . . . F304 F 0.0478(5) 0.9601(4) 0.1193(4) 0.104(3) Uani 1 1 d . . . F305 F 0.1699(7) 0.9183(3) 0.2299(3) 0.101(2) Uani 1 1 d . . . F306 F 0.1066(5) 1.0783(3) 0.0846(3) 0.0788(18) Uani 1 1 d . . . P401 P 0.55501(18) 0.22466(11) 0.17976(10) 0.0202(4) Uani 1 1 d . . . F401 F 0.4481(4) 0.2702(2) 0.1076(2) 0.0358(11) Uani 1 1 d . . . F402 F 0.6703(5) 0.2122(4) 0.1195(2) 0.0782(19) Uani 1 1 d . . . F403 F 0.6617(4) 0.1793(3) 0.2511(2) 0.0455(12) Uani 1 1 d . . . F404 F 0.4369(5) 0.2384(3) 0.2394(2) 0.0680(16) Uani 1 1 d . . . F405 F 0.5220(7) 0.1430(3) 0.1881(3) 0.097(2) Uani 1 1 d . . . F406 F 0.5847(6) 0.3079(3) 0.1716(3) 0.079(2) 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 0.0180(4) 0.0133(4) 0.0181(4) -0.0065(3) 0.0000(3) -0.0061(3) Cu2 0.0195(5) 0.0138(4) 0.0174(4) -0.0053(3) -0.0013(3) -0.0057(3) N11 0.026(3) 0.011(3) 0.022(3) -0.001(2) -0.004(2) -0.012(2) N12 0.018(3) 0.017(3) 0.014(3) -0.008(2) -0.002(2) -0.001(2) N13 0.018(3) 0.022(3) 0.021(3) -0.007(2) 0.000(2) -0.004(3) O11 0.020(2) 0.016(2) 0.018(2) -0.0050(18) 0.0001(19) -0.009(2) O12 0.026(3) 0.019(2) 0.032(3) -0.013(2) 0.003(2) -0.013(2) C11 0.021(4) 0.019(3) 0.014(3) -0.003(3) -0.002(3) -0.010(3) C12 0.020(4) 0.022(4) 0.015(3) -0.010(3) -0.001(3) -0.006(3) C13 0.017(4) 0.017(3) 0.018(3) -0.009(3) 0.000(3) -0.006(3) C14 0.022(4) 0.012(3) 0.025(4) -0.005(3) -0.006(3) -0.008(3) C15 0.027(4) 0.015(3) 0.018(3) -0.003(3) -0.010(3) -0.003(3) C16 0.015(3) 0.014(3) 0.018(3) -0.005(3) -0.003(3) -0.001(3) C17 0.010(3) 0.018(3) 0.019(3) -0.004(3) 0.000(3) -0.005(3) C18 0.023(4) 0.018(3) 0.025(4) -0.009(3) 0.001(3) -0.007(3) C19 0.020(4) 0.026(4) 0.022(4) -0.009(3) 0.005(3) -0.011(3) C20 0.014(4) 0.027(4) 0.026(4) -0.010(3) -0.004(3) -0.006(3) C21 0.020(4) 0.020(4) 0.023(4) -0.008(3) -0.006(3) -0.002(3) C22 0.039(5) 0.036(4) 0.025(4) -0.004(3) 0.005(3) -0.023(4) N31 0.021(3) 0.011(3) 0.023(3) -0.009(2) -0.006(2) -0.006(2) N32 0.022(3) 0.012(3) 0.018(3) -0.005(2) -0.002(2) -0.006(2) N33 0.019(3) 0.023(3) 0.023(3) -0.011(2) 0.000(2) -0.007(3) O31 0.023(3) 0.023(2) 0.020(2) -0.011(2) 0.0021(19) -0.009(2) O32 0.023(3) 0.020(2) 0.025(3) -0.012(2) 0.004(2) -0.012(2) C31 0.020(4) 0.016(3) 0.024(4) -0.008(3) -0.003(3) -0.002(3) C32 0.020(4) 0.015(3) 0.016(3) -0.003(3) -0.001(3) -0.007(3) C33 0.018(4) 0.011(3) 0.020(3) -0.006(3) -0.007(3) 0.004(3) C34 0.025(4) 0.019(3) 0.019(3) -0.003(3) -0.004(3) -0.009(3) C35 0.023(4) 0.011(3) 0.021(3) -0.001(3) -0.003(3) -0.002(3) C36 0.021(4) 0.012(3) 0.013(3) 0.000(3) -0.005(3) 0.004(3) C37 0.024(4) 0.016(3) 0.018(3) -0.001(3) -0.008(3) -0.004(3) C38 0.039(4) 0.014(3) 0.022(4) -0.003(3) -0.007(3) 0.001(3) C39 0.022(4) 0.022(4) 0.015(3) -0.009(3) 0.003(3) -0.009(3) C40 0.024(4) 0.020(4) 0.032(4) -0.006(3) 0.004(3) -0.012(3) C41 0.038(5) 0.025(4) 0.027(4) -0.013(3) 0.012(3) -0.017(4) C42 0.029(4) 0.029(4) 0.027(4) -0.001(3) -0.001(3) -0.008(3) N51 0.024(3) 0.012(3) 0.020(3) -0.005(2) -0.003(2) -0.011(2) N52 0.019(3) 0.012(3) 0.023(3) -0.007(2) 0.003(2) -0.006(2) N53 0.019(3) 0.014(3) 0.020(3) -0.008(2) -0.001(2) -0.002(2) O51 0.022(3) 0.020(2) 0.019(2) -0.0101(19) 0.0013(19) -0.005(2) O52 0.037(3) 0.019(2) 0.028(3) -0.011(2) 0.003(2) -0.013(2) C51 0.009(3) 0.023(4) 0.019(3) -0.009(3) 0.000(3) -0.004(3) C52 0.015(3) 0.013(3) 0.017(3) -0.001(3) -0.004(3) -0.004(3) C53 0.019(4) 0.017(3) 0.015(3) -0.001(3) -0.005(3) -0.006(3) C54 0.028(4) 0.016(3) 0.025(4) -0.005(3) 0.001(3) -0.011(3) C55 0.031(4) 0.019(3) 0.017(3) -0.009(3) 0.002(3) -0.011(3) C56 0.019(4) 0.015(3) 0.014(3) 0.000(3) -0.001(3) 0.001(3) C57 0.017(4) 0.014(3) 0.024(4) -0.001(3) -0.003(3) -0.002(3) C58 0.030(4) 0.027(4) 0.023(4) -0.007(3) -0.005(3) -0.011(3) C59 0.017(4) 0.011(3) 0.026(4) -0.003(3) -0.003(3) 0.005(3) C60 0.019(4) 0.032(4) 0.026(4) -0.014(3) 0.003(3) -0.010(3) C61 0.016(4) 0.032(4) 0.025(4) -0.013(3) -0.004(3) -0.002(3) C62 0.031(4) 0.034(4) 0.022(4) -0.006(3) 0.004(3) -0.015(4) N71 0.029(3) 0.015(3) 0.016(3) -0.004(2) -0.006(2) -0.008(3) N72 0.030(4) 0.023(3) 0.022(3) -0.010(3) -0.002(3) -0.007(3) N73 0.024(3) 0.028(3) 0.015(3) -0.008(2) -0.001(2) -0.012(3) O71 0.024(3) 0.018(2) 0.021(2) -0.0093(19) -0.004(2) -0.005(2) O72 0.032(3) 0.015(2) 0.024(3) -0.0101(19) 0.006(2) -0.011(2) C71 0.019(4) 0.015(3) 0.018(3) -0.003(3) -0.004(3) -0.004(3) C72 0.021(4) 0.011(3) 0.013(3) -0.001(3) -0.005(3) 0.005(3) C73 0.017(4) 0.018(3) 0.015(3) -0.008(3) -0.004(3) 0.001(3) C74 0.028(4) 0.011(3) 0.026(4) -0.003(3) -0.008(3) -0.008(3) C75 0.026(4) 0.016(3) 0.022(4) -0.008(3) -0.009(3) -0.003(3) C76 0.023(4) 0.013(3) 0.017(3) -0.002(3) -0.007(3) 0.005(3) C77 0.020(4) 0.018(3) 0.015(3) -0.002(3) -0.003(3) -0.005(3) C78 0.026(4) 0.017(4) 0.031(4) -0.004(3) -0.008(3) 0.003(3) C79 0.019(4) 0.025(4) 0.025(4) -0.012(3) -0.001(3) -0.008(3) C80 0.019(4) 0.031(4) 0.030(4) -0.018(3) 0.012(3) -0.009(3) C81 0.037(5) 0.027(4) 0.027(4) -0.015(3) 0.010(3) -0.019(4) C82 0.034(4) 0.020(4) 0.029(4) 0.001(3) -0.009(3) -0.010(3) P101 0.0183(10) 0.0194(9) 0.0228(9) -0.0057(7) -0.0025(7) -0.0052(8) F101 0.047(3) 0.027(2) 0.052(3) -0.014(2) 0.014(2) 0.000(2) F102 0.036(3) 0.074(3) 0.031(2) -0.017(2) -0.007(2) -0.025(3) F103 0.054(3) 0.021(2) 0.049(3) -0.005(2) 0.009(2) -0.002(2) F104 0.041(3) 0.053(3) 0.030(2) -0.002(2) -0.011(2) -0.032(2) F105 0.027(2) 0.041(3) 0.024(2) 0.0074(18) -0.0053(18) -0.012(2) F106 0.021(2) 0.038(2) 0.033(2) -0.0065(19) 0.0012(17) -0.0165(19) P201 0.0232(10) 0.0239(10) 0.0327(11) -0.0160(8) 0.0006(8) -0.0033(8) F201 0.036(3) 0.052(3) 0.152(5) -0.065(4) 0.023(3) -0.007(3) F202 0.049(3) 0.040(3) 0.059(3) -0.027(2) 0.014(2) -0.029(2) F203 0.036(3) 0.033(3) 0.062(3) -0.019(2) 0.012(2) 0.000(2) F204 0.040(3) 0.041(3) 0.073(3) -0.029(2) -0.003(2) -0.017(2) F205 0.080(4) 0.096(4) 0.026(3) -0.016(3) 0.012(2) -0.063(3) F206 0.079(4) 0.053(3) 0.049(3) 0.002(2) -0.032(3) -0.007(3) P301 0.0258(11) 0.0255(10) 0.0319(11) -0.0119(9) 0.0058(8) -0.0062(9) F301 0.030(2) 0.040(3) 0.041(3) -0.023(2) 0.0056(19) -0.007(2) F302 0.031(3) 0.073(4) 0.082(4) -0.057(3) -0.006(2) -0.001(3) F303 0.040(3) 0.062(3) 0.104(4) -0.054(3) 0.033(3) -0.020(3) F304 0.042(3) 0.165(7) 0.186(7) -0.151(6) 0.040(4) -0.051(4) F305 0.140(6) 0.045(3) 0.070(4) 0.016(3) 0.052(4) -0.003(4) F306 0.069(4) 0.063(4) 0.062(4) 0.014(3) -0.014(3) 0.012(3) P401 0.0212(10) 0.0219(9) 0.0193(9) -0.0071(7) -0.0016(7) -0.0073(8) F401 0.025(2) 0.053(3) 0.020(2) 0.0042(19) -0.0085(17) -0.015(2) F402 0.037(3) 0.135(5) 0.024(3) -0.012(3) 0.000(2) 0.023(3) F403 0.021(2) 0.078(3) 0.021(2) 0.000(2) -0.0067(18) -0.007(2) F404 0.040(3) 0.105(4) 0.028(3) -0.002(3) 0.005(2) 0.006(3) F405 0.203(7) 0.026(3) 0.070(4) 0.011(3) -0.058(4) -0.058(4) F406 0.154(6) 0.047(3) 0.054(3) -0.004(3) -0.030(3) -0.061(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 O31 1.890(4) . ? Cu1 O11 1.893(4) . ? Cu1 N31 1.933(5) . ? Cu1 N11 1.941(5) . ? Cu2 O51 1.892(4) . ? Cu2 O71 1.903(4) . ? Cu2 N51 1.937(5) . ? Cu2 N71 1.943(5) . ? N11 C11 1.291(7) . ? N11 O12 1.402(6) . ? N12 C19 1.332(7) . ? N12 C20 1.372(7) . ? N12 C18 1.478(7) . ? N13 C19 1.323(7) . ? N13 C21 1.381(8) . ? N13 C22 1.466(8) . ? O11 C13 1.327(7) . ? O12 H12 0.8400 . ? C11 C12 1.426(8) . ? C11 H11 0.9500 . ? C12 C17 1.409(8) . ? C12 C13 1.433(8) . ? C13 C14 1.395(8) . ? C14 C15 1.380(8) . ? C14 H14 0.9500 . ? C15 C16 1.397(8) . ? C15 H15 0.9500 . ? C16 C17 1.373(8) . ? C16 C18 1.512(8) . ? C17 H17 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19 0.9500 . ? C20 C21 1.349(8) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N31 C31 1.292(7) . ? N31 O32 1.396(5) . ? N32 C39 1.335(8) . ? N32 C40 1.379(8) . ? N32 C38 1.463(7) . ? N33 C39 1.314(7) . ? N33 C41 1.356(8) . ? N33 C42 1.463(8) . ? O31 C33 1.328(7) . ? O32 H32 0.8400 . ? C31 C32 1.439(8) . ? C31 H31 0.9500 . ? C32 C37 1.409(8) . ? C32 C33 1.417(8) . ? C33 C34 1.398(8) . ? C34 C35 1.369(8) . ? C34 H34 0.9500 . ? C35 C36 1.390(8) . ? C35 H35 0.9500 . ? C36 C37 1.399(8) . ? C36 C38 1.499(9) . ? C37 H37 0.9500 . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 H39 0.9500 . ? C40 C41 1.354(9) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? N51 C51 1.289(7) . ? N51 O52 1.391(6) . ? N52 C59 1.311(7) . ? N52 C60 1.379(8) . ? N52 C58 1.480(7) . ? N53 C59 1.329(7) . ? N53 C61 1.375(8) . ? N53 C62 1.465(7) . ? O51 C53 1.324(7) . ? O52 H52 0.8400 . ? C51 C52 1.435(8) . ? C51 H51 0.9500 . ? C52 C53 1.417(8) . ? C52 C57 1.417(8) . ? C53 C54 1.405(8) . ? C54 C55 1.370(8) . ? C54 H54 0.9500 . ? C55 C56 1.406(8) . ? C55 H55 0.9500 . ? C56 C57 1.373(8) . ? C56 C58 1.510(8) . ? C57 H57 0.9500 . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C59 H59 0.9500 . ? C60 C61 1.342(8) . ? C60 H60 0.9500 . ? C61 H61 0.9500 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? N71 C71 1.274(7) . ? N71 O72 1.394(6) . ? N72 C79 1.324(8) . ? N72 C80 1.382(8) . ? N72 C78 1.490(8) . ? N73 C79 1.334(7) . ? N73 C81 1.352(8) . ? N73 C82 1.472(8) . ? O71 C73 1.320(7) . ? O72 H72 0.8400 . ? C71 C72 1.456(8) . ? C71 H71 0.9500 . ? C72 C77 1.398(8) . ? C72 C73 1.421(8) . ? C73 C74 1.413(8) . ? C74 C75 1.369(9) . ? C74 H74 0.9500 . ? C75 C76 1.398(9) . ? C75 H75 0.9500 . ? C76 C77 1.389(8) . ? C76 C78 1.506(8) . ? C77 H77 0.9500 . ? C78 H78A 0.9900 . ? C78 H78B 0.9900 . ? C79 H79 0.9500 . ? C80 C81 1.357(9) . ? C80 H80 0.9500 . ? C81 H81 0.9500 . ? C82 H82A 0.9800 . ? C82 H82B 0.9800 . ? C82 H82C 0.9800 . ? P101 F103 1.584(4) . ? P101 F101 1.586(4) . ? P101 F102 1.587(4) . ? P101 F106 1.598(4) . ? P101 F104 1.606(4) . ? P101 F105 1.606(4) . ? P201 F205 1.569(4) . ? P201 F203 1.573(4) . ? P201 F201 1.578(5) . ? P201 F206 1.598(5) . ? P201 F204 1.604(4) . ? P201 F202 1.606(4) . ? P301 F305 1.554(5) . ? P301 F304 1.564(5) . ? P301 F306 1.580(5) . ? P301 F303 1.588(5) . ? P301 F302 1.588(4) . ? P301 F301 1.601(4) . ? P401 F405 1.552(5) . ? P401 F402 1.561(5) . ? P401 F406 1.567(5) . ? P401 F404 1.578(5) . ? P401 F403 1.593(4) . ? P401 F401 1.605(4) . ? 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 O31 Cu1 O11 178.19(18) . . ? O31 Cu1 N31 92.29(19) . . ? O11 Cu1 N31 87.97(19) . . ? O31 Cu1 N11 87.59(19) . . ? O11 Cu1 N11 92.26(19) . . ? N31 Cu1 N11 176.4(2) . . ? O51 Cu2 O71 177.55(17) . . ? O51 Cu2 N51 92.01(19) . . ? O71 Cu2 N51 88.51(19) . . ? O51 Cu2 N71 86.80(19) . . ? O71 Cu2 N71 92.8(2) . . ? N51 Cu2 N71 177.9(2) . . ? C11 N11 O12 113.9(5) . . ? C11 N11 Cu1 128.4(4) . . ? O12 N11 Cu1 117.7(4) . . ? C19 N12 C20 108.7(5) . . ? C19 N12 C18 125.6(5) . . ? C20 N12 C18 125.5(5) . . ? C19 N13 C21 108.8(5) . . ? C19 N13 C22 124.8(5) . . ? C21 N13 C22 126.5(5) . . ? C13 O11 Cu1 129.1(4) . . ? N11 O12 H12 109.5 . . ? N11 C11 C12 123.4(6) . . ? N11 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C17 C12 C11 117.5(6) . . ? C17 C12 C13 117.9(5) . . ? C11 C12 C13 124.6(6) . . ? O11 C13 C14 119.5(5) . . ? O11 C13 C12 122.2(5) . . ? C14 C13 C12 118.3(6) . . ? C15 C14 C13 121.9(6) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.4(6) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 118.6(6) . . ? C17 C16 C18 120.9(5) . . ? C15 C16 C18 120.3(5) . . ? C16 C17 C12 122.8(6) . . ? C16 C17 H17 118.6 . . ? C12 C17 H17 118.6 . . ? N12 C18 C16 109.5(5) . . ? N12 C18 H18A 109.8 . . ? C16 C18 H18A 109.8 . . ? N12 C18 H18B 109.8 . . ? C16 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? N13 C19 N12 108.5(5) . . ? N13 C19 H19 125.8 . . ? N12 C19 H19 125.8 . . ? C21 C20 N12 107.2(6) . . ? C21 C20 H20 126.4 . . ? N12 C20 H20 126.4 . . ? C20 C21 N13 106.8(6) . . ? C20 C21 H21 126.6 . . ? N13 C21 H21 126.6 . . ? N13 C22 H22A 109.5 . . ? N13 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N13 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C31 N31 O32 113.4(5) . . ? C31 N31 Cu1 127.9(4) . . ? O32 N31 Cu1 118.6(4) . . ? C39 N32 C40 108.2(5) . . ? C39 N32 C38 127.4(6) . . ? C40 N32 C38 124.3(5) . . ? C39 N33 C41 108.4(6) . . ? C39 N33 C42 124.1(6) . . ? C41 N33 C42 126.9(6) . . ? C33 O31 Cu1 129.3(4) . . ? N31 O32 H32 109.5 . . ? N31 C31 C32 123.7(6) . . ? N31 C31 H31 118.1 . . ? C32 C31 H31 118.1 . . ? C37 C32 C33 118.5(5) . . ? C37 C32 C31 117.5(6) . . ? C33 C32 C31 124.0(6) . . ? O31 C33 C34 118.8(6) . . ? O31 C33 C32 122.5(5) . . ? C34 C33 C32 118.6(6) . . ? C35 C34 C33 121.6(6) . . ? C35 C34 H34 119.2 . . ? C33 C34 H34 119.2 . . ? C34 C35 C36 121.4(6) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C35 C36 C37 117.9(6) . . ? C35 C36 C38 121.2(6) . . ? C37 C36 C38 120.8(6) . . ? C36 C37 C32 121.9(6) . . ? C36 C37 H37 119.0 . . ? C32 C37 H37 119.0 . . ? N32 C38 C36 112.6(5) . . ? N32 C38 H38A 109.1 . . ? C36 C38 H38A 109.1 . . ? N32 C38 H38B 109.1 . . ? C36 C38 H38B 109.1 . . ? H38A C38 H38B 107.8 . . ? N33 C39 N32 109.2(6) . . ? N33 C39 H39 125.4 . . ? N32 C39 H39 125.4 . . ? C41 C40 N32 105.8(6) . . ? C41 C40 H40 127.1 . . ? N32 C40 H40 127.1 . . ? C40 C41 N33 108.4(6) . . ? C40 C41 H41 125.8 . . ? N33 C41 H41 125.8 . . ? N33 C42 H42A 109.5 . . ? N33 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? N33 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C51 N51 O52 113.7(5) . . ? C51 N51 Cu2 127.7(4) . . ? O52 N51 Cu2 118.7(4) . . ? C59 N52 C60 108.4(5) . . ? C59 N52 C58 125.7(5) . . ? C60 N52 C58 125.9(5) . . ? C59 N53 C61 107.5(5) . . ? C59 N53 C62 125.1(5) . . ? C61 N53 C62 127.4(5) . . ? C53 O51 Cu2 129.5(4) . . ? N51 O52 H52 109.5 . . ? N51 C51 C52 124.5(6) . . ? N51 C51 H51 117.7 . . ? C52 C51 H51 117.7 . . ? C53 C52 C57 118.6(5) . . ? C53 C52 C51 123.5(6) . . ? C57 C52 C51 117.9(5) . . ? O51 C53 C54 119.1(6) . . ? O51 C53 C52 122.7(5) . . ? C54 C53 C52 118.1(6) . . ? C55 C54 C53 121.8(6) . . ? C55 C54 H54 119.1 . . ? C53 C54 H54 119.1 . . ? C54 C55 C56 120.7(6) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.6 . . ? C57 C56 C55 118.4(6) . . ? C57 C56 C58 121.4(6) . . ? C55 C56 C58 120.2(6) . . ? C56 C57 C52 122.3(6) . . ? C56 C57 H57 118.9 . . ? C52 C57 H57 118.9 . . ? N52 C58 C56 109.9(5) . . ? N52 C58 H58A 109.7 . . ? C56 C58 H58A 109.7 . . ? N52 C58 H58B 109.7 . . ? C56 C58 H58B 109.7 . . ? H58A C58 H58B 108.2 . . ? N52 C59 N53 109.7(6) . . ? N52 C59 H59 125.2 . . ? N53 C59 H59 125.2 . . ? C61 C60 N52 106.8(6) . . ? C61 C60 H60 126.6 . . ? N52 C60 H60 126.6 . . ? C60 C61 N53 107.7(6) . . ? C60 C61 H61 126.1 . . ? N53 C61 H61 126.1 . . ? N53 C62 H62A 109.5 . . ? N53 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? N53 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C71 N71 O72 113.9(5) . . ? C71 N71 Cu2 127.7(4) . . ? O72 N71 Cu2 118.4(4) . . ? C79 N72 C80 108.5(6) . . ? C79 N72 C78 125.5(6) . . ? C80 N72 C78 126.0(6) . . ? C79 N73 C81 108.5(6) . . ? C79 N73 C82 124.3(6) . . ? C81 N73 C82 126.8(6) . . ? C73 O71 Cu2 128.2(4) . . ? N71 O72 H72 109.5 . . ? N71 C71 C72 124.4(6) . . ? N71 C71 H71 117.8 . . ? C72 C71 H71 117.8 . . ? C77 C72 C73 119.7(6) . . ? C77 C72 C71 117.2(6) . . ? C73 C72 C71 123.0(6) . . ? O71 C73 C74 119.8(6) . . ? O71 C73 C72 123.8(5) . . ? C74 C73 C72 116.4(6) . . ? C75 C74 C73 122.8(6) . . ? C75 C74 H74 118.6 . . ? C73 C74 H74 118.6 . . ? C74 C75 C76 120.9(6) . . ? C74 C75 H75 119.5 . . ? C76 C75 H75 119.5 . . ? C77 C76 C75 117.5(6) . . ? C77 C76 C78 119.8(6) . . ? C75 C76 C78 122.4(6) . . ? C76 C77 C72 122.6(6) . . ? C76 C77 H77 118.7 . . ? C72 C77 H77 118.7 . . ? N72 C78 C76 109.5(5) . . ? N72 C78 H78A 109.8 . . ? C76 C78 H78A 109.8 . . ? N72 C78 H78B 109.8 . . ? C76 C78 H78B 109.8 . . ? H78A C78 H78B 108.2 . . ? N72 C79 N73 108.7(6) . . ? N72 C79 H79 125.6 . . ? N73 C79 H79 125.6 . . ? C81 C80 N72 106.1(6) . . ? C81 C80 H80 126.9 . . ? N72 C80 H80 126.9 . . ? N73 C81 C80 108.1(6) . . ? N73 C81 H81 126.0 . . ? C80 C81 H81 126.0 . . ? N73 C82 H82A 109.5 . . ? N73 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? N73 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? F103 P101 F101 179.0(2) . . ? F103 P101 F102 90.5(2) . . ? F101 P101 F102 90.4(2) . . ? F103 P101 F106 90.1(2) . . ? F101 P101 F106 89.6(2) . . ? F102 P101 F106 90.7(2) . . ? F103 P101 F104 90.1(2) . . ? F101 P101 F104 89.0(2) . . ? F102 P101 F104 179.4(3) . . ? F106 P101 F104 89.5(2) . . ? F103 P101 F105 90.3(2) . . ? F101 P101 F105 90.0(2) . . ? F102 P101 F105 90.3(2) . . ? F106 P101 F105 178.9(2) . . ? F104 P101 F105 89.5(2) . . ? F205 P201 F203 91.3(3) . . ? F205 P201 F201 91.7(3) . . ? F203 P201 F201 177.0(3) . . ? F205 P201 F206 179.2(3) . . ? F203 P201 F206 88.0(3) . . ? F201 P201 F206 89.0(3) . . ? F205 P201 F204 90.2(2) . . ? F203 P201 F204 90.7(2) . . ? F201 P201 F204 89.6(3) . . ? F206 P201 F204 90.3(2) . . ? F205 P201 F202 89.7(2) . . ? F203 P201 F202 89.6(2) . . ? F201 P201 F202 90.2(2) . . ? F206 P201 F202 89.8(3) . . ? F204 P201 F202 179.7(3) . . ? F305 P301 F304 91.5(4) . . ? F305 P301 F306 177.3(4) . . ? F304 P301 F306 90.8(4) . . ? F305 P301 F303 91.4(3) . . ? F304 P301 F303 90.7(3) . . ? F306 P301 F303 90.1(3) . . ? F305 P301 F302 90.2(3) . . ? F304 P301 F302 178.2(4) . . ? F306 P301 F302 87.5(3) . . ? F303 P301 F302 89.7(2) . . ? F305 P301 F301 89.7(3) . . ? F304 P301 F301 89.4(2) . . ? F306 P301 F301 88.8(3) . . ? F303 P301 F301 178.9(3) . . ? F302 P301 F301 90.2(2) . . ? F405 P401 F402 91.9(4) . . ? F405 P401 F406 178.7(4) . . ? F402 P401 F406 89.2(3) . . ? F405 P401 F404 88.4(3) . . ? F402 P401 F404 179.0(3) . . ? F406 P401 F404 90.5(3) . . ? F405 P401 F403 90.4(3) . . ? F402 P401 F403 91.4(2) . . ? F406 P401 F403 90.4(3) . . ? F404 P401 F403 89.6(2) . . ? F405 P401 F401 89.6(2) . . ? F402 P401 F401 88.3(2) . . ? F406 P401 F401 89.7(2) . . ? F404 P401 F401 90.7(2) . . ? F403 P401 F401 179.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O31 Cu1 N11 C11 179.0(5) . . . . ? O11 Cu1 N11 C11 0.8(5) . . . . ? O31 Cu1 N11 O12 -3.0(4) . . . . ? O11 Cu1 N11 O12 178.8(4) . . . . ? N31 Cu1 O11 C13 175.8(5) . . . . ? N11 Cu1 O11 C13 -0.6(5) . . . . ? O12 N11 C11 C12 -179.4(5) . . . . ? Cu1 N11 C11 C12 -1.3(9) . . . . ? N11 C11 C12 C17 -180.0(6) . . . . ? N11 C11 C12 C13 1.4(9) . . . . ? Cu1 O11 C13 C14 -178.6(4) . . . . ? Cu1 O11 C13 C12 0.9(8) . . . . ? C17 C12 C13 O11 -179.8(5) . . . . ? C11 C12 C13 O11 -1.2(9) . . . . ? C17 C12 C13 C14 -0.3(8) . . . . ? C11 C12 C13 C14 178.3(6) . . . . ? O11 C13 C14 C15 179.1(5) . . . . ? C12 C13 C14 C15 -0.4(9) . . . . ? C13 C14 C15 C16 0.6(9) . . . . ? C14 C15 C16 C17 -0.1(9) . . . . ? C14 C15 C16 C18 -176.0(5) . . . . ? C15 C16 C17 C12 -0.7(9) . . . . ? C18 C16 C17 C12 175.3(6) . . . . ? C11 C12 C17 C16 -177.9(5) . . . . ? C13 C12 C17 C16 0.8(9) . . . . ? C19 N12 C18 C16 111.8(7) . . . . ? C20 N12 C18 C16 -63.1(7) . . . . ? C17 C16 C18 N12 -73.6(7) . . . . ? C15 C16 C18 N12 102.3(6) . . . . ? C21 N13 C19 N12 1.1(7) . . . . ? C22 N13 C19 N12 179.6(6) . . . . ? C20 N12 C19 N13 -0.7(7) . . . . ? C18 N12 C19 N13 -176.4(5) . . . . ? C19 N12 C20 C21 0.0(7) . . . . ? C18 N12 C20 C21 175.7(5) . . . . ? N12 C20 C21 N13 0.6(7) . . . . ? C19 N13 C21 C20 -1.1(7) . . . . ? C22 N13 C21 C20 -179.5(6) . . . . ? O31 Cu1 N31 C31 5.4(5) . . . . ? O11 Cu1 N31 C31 -176.4(5) . . . . ? O31 Cu1 N31 O32 -176.8(4) . . . . ? O11 Cu1 N31 O32 1.5(4) . . . . ? N31 Cu1 O31 C33 -4.0(5) . . . . ? N11 Cu1 O31 C33 172.3(5) . . . . ? O32 N31 C31 C32 178.4(5) . . . . ? Cu1 N31 C31 C32 -3.6(9) . . . . ? N31 C31 C32 C37 -179.9(6) . . . . ? N31 C31 C32 C33 -1.4(9) . . . . ? Cu1 O31 C33 C34 -179.7(4) . . . . ? Cu1 O31 C33 C32 1.0(8) . . . . ? C37 C32 C33 O31 -178.7(5) . . . . ? C31 C32 C33 O31 2.8(9) . . . . ? C37 C32 C33 C34 2.0(8) . . . . ? C31 C32 C33 C34 -176.5(6) . . . . ? O31 C33 C34 C35 179.2(5) . . . . ? C32 C33 C34 C35 -1.5(9) . . . . ? C33 C34 C35 C36 -1.2(9) . . . . ? C34 C35 C36 C37 3.2(9) . . . . ? C34 C35 C36 C38 178.7(5) . . . . ? C35 C36 C37 C32 -2.6(8) . . . . ? C38 C36 C37 C32 -178.2(5) . . . . ? C33 C32 C37 C36 0.1(9) . . . . ? C31 C32 C37 C36 178.7(5) . . . . ? C39 N32 C38 C36 19.3(9) . . . . ? C40 N32 C38 C36 -160.9(6) . . . . ? C35 C36 C38 N32 -98.8(7) . . . . ? C37 C36 C38 N32 76.6(7) . . . . ? C41 N33 C39 N32 0.9(7) . . . . ? C42 N33 C39 N32 172.7(5) . . . . ? C40 N32 C39 N33 0.1(7) . . . . ? C38 N32 C39 N33 179.9(5) . . . . ? C39 N32 C40 C41 -1.0(7) . . . . ? C38 N32 C40 C41 179.1(5) . . . . ? N32 C40 C41 N33 1.6(7) . . . . ? C39 N33 C41 C40 -1.6(7) . . . . ? C42 N33 C41 C40 -173.0(6) . . . . ? O51 Cu2 N51 C51 2.2(5) . . . . ? O71 Cu2 N51 C51 -175.4(5) . . . . ? O51 Cu2 N51 O52 -178.7(4) . . . . ? O71 Cu2 N51 O52 3.7(4) . . . . ? N51 Cu2 O51 C53 0.7(5) . . . . ? N71 Cu2 O51 C53 -177.6(5) . . . . ? O52 N51 C51 C52 178.1(5) . . . . ? Cu2 N51 C51 C52 -2.8(9) . . . . ? N51 C51 C52 C53 0.1(9) . . . . ? N51 C51 C52 C57 -179.3(6) . . . . ? Cu2 O51 C53 C54 177.4(4) . . . . ? Cu2 O51 C53 C52 -3.0(8) . . . . ? C57 C52 C53 O51 -177.8(5) . . . . ? C51 C52 C53 O51 2.8(9) . . . . ? C57 C52 C53 C54 1.9(8) . . . . ? C51 C52 C53 C54 -177.6(5) . . . . ? O51 C53 C54 C55 177.9(6) . . . . ? C52 C53 C54 C55 -1.8(9) . . . . ? C53 C54 C55 C56 0.2(10) . . . . ? C54 C55 C56 C57 1.2(9) . . . . ? C54 C55 C56 C58 177.7(6) . . . . ? C55 C56 C57 C52 -1.0(9) . . . . ? C58 C56 C57 C52 -177.5(5) . . . . ? C53 C52 C57 C56 -0.5(9) . . . . ? C51 C52 C57 C56 178.9(5) . . . . ? C59 N52 C58 C56 -123.4(6) . . . . ? C60 N52 C58 C56 54.8(8) . . . . ? C57 C56 C58 N52 80.5(7) . . . . ? C55 C56 C58 N52 -95.9(7) . . . . ? C60 N52 C59 N53 0.0(7) . . . . ? C58 N52 C59 N53 178.4(5) . . . . ? C61 N53 C59 N52 0.3(7) . . . . ? C62 N53 C59 N52 -176.2(5) . . . . ? C59 N52 C60 C61 -0.2(7) . . . . ? C58 N52 C60 C61 -178.7(5) . . . . ? N52 C60 C61 N53 0.4(7) . . . . ? C59 N53 C61 C60 -0.4(7) . . . . ? C62 N53 C61 C60 175.9(6) . . . . ? O51 Cu2 N71 C71 -179.1(5) . . . . ? O71 Cu2 N71 C71 -1.6(5) . . . . ? O51 Cu2 N71 O72 3.8(4) . . . . ? O71 Cu2 N71 O72 -178.7(4) . . . . ? N51 Cu2 O71 C73 -178.2(5) . . . . ? N71 Cu2 O71 C73 0.1(5) . . . . ? O72 N71 C71 C72 179.9(5) . . . . ? Cu2 N71 C71 C72 2.7(9) . . . . ? N71 C71 C72 C77 177.0(6) . . . . ? N71 C71 C72 C73 -2.2(9) . . . . ? Cu2 O71 C73 C74 -178.4(4) . . . . ? Cu2 O71 C73 C72 0.1(8) . . . . ? C77 C72 C73 O71 -178.5(5) . . . . ? C71 C72 C73 O71 0.7(9) . . . . ? C77 C72 C73 C74 0.1(8) . . . . ? C71 C72 C73 C74 179.3(5) . . . . ? O71 C73 C74 C75 178.5(6) . . . . ? C72 C73 C74 C75 -0.2(9) . . . . ? C73 C74 C75 C76 -0.2(9) . . . . ? C74 C75 C76 C77 0.8(9) . . . . ? C74 C75 C76 C78 -173.1(6) . . . . ? C75 C76 C77 C72 -0.9(9) . . . . ? C78 C76 C77 C72 173.1(5) . . . . ? C73 C72 C77 C76 0.5(9) . . . . ? C71 C72 C77 C76 -178.8(5) . . . . ? C79 N72 C78 C76 -23.3(8) . . . . ? C80 N72 C78 C76 159.1(6) . . . . ? C77 C76 C78 N72 -80.0(7) . . . . ? C75 C76 C78 N72 93.7(7) . . . . ? C80 N72 C79 N73 -1.7(7) . . . . ? C78 N72 C79 N73 -179.6(5) . . . . ? C81 N73 C79 N72 0.3(7) . . . . ? C82 N73 C79 N72 -173.0(5) . . . . ? C79 N72 C80 C81 2.4(7) . . . . ? C78 N72 C80 C81 -179.7(5) . . . . ? C79 N73 C81 C80 1.2(7) . . . . ? C82 N73 C81 C80 174.3(6) . . . . ? N72 C80 C81 N73 -2.2(7) . . . . ? _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.906 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.140 # Attachment 'Compound_5.cif' data_rs0213 _database_code_depnum_ccdc_archive 'CCDC 693565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 Cu F12 N6 O4 P2' _chemical_formula_weight 842.02 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.492(4) _cell_length_b 10.988(5) _cell_length_c 35.208(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.442(12) _cell_angle_gamma 90.00 _cell_volume 3284(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1700 _exptl_absorpt_coefficient_mu 0.875 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.480 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12988 _diffrn_reflns_av_R_equivalents 0.1029 _diffrn_reflns_av_sigmaI/netI 0.1644 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 25.23 _reflns_number_total 5754 _reflns_number_gt 3049 _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. Hydrogen atoms on water molecules could not be located. R1 value is greater than 0.10 as data was a little weak and the complex is large - overall though the struture refined nicely. ; _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^)+(0.0924P)^2^+17.3450P] 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 5754 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2015 _refine_ls_R_factor_gt 0.1151 _refine_ls_wR_factor_ref 0.2935 _refine_ls_wR_factor_gt 0.2477 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.73127(16) 0.50177(13) 0.50506(3) 0.0366(4) Uani 1 1 d . . . N11 N 0.8405(12) 0.5624(10) 0.4615(3) 0.042(3) Uani 1 1 d . . . N12 N 1.1527(11) 0.0678(11) 0.3630(3) 0.045(3) Uani 1 1 d . . . N13 N 1.0578(11) -0.0871(10) 0.3350(3) 0.046(3) Uani 1 1 d . . . N14 N 0.6330(11) 0.6589(9) 0.5051(2) 0.039(2) Uani 1 1 d . . . N15 N 0.3167(11) 0.7282(9) 0.6890(3) 0.039(2) Uani 1 1 d . . . N16 N 0.4678(12) 0.7786(10) 0.7358(3) 0.049(3) Uani 1 1 d . . . O11 O 0.8076(9) 0.3390(7) 0.49877(19) 0.039(2) Uani 1 1 d . . . O12 O 0.6473(9) 0.4552(7) 0.55275(19) 0.0380(19) Uani 1 1 d . . . C11 C 0.8175(16) 0.6958(12) 0.4547(3) 0.055(4) Uani 1 1 d . . . H11A H 0.9007 0.7431 0.4683 0.065 Uiso 1 1 calc R . . H11B H 0.8216 0.7144 0.4273 0.065 Uiso 1 1 calc R . . C12 C 0.9352(14) 0.4990(13) 0.4402(3) 0.048(3) Uani 1 1 d . . . H12 H 0.9863 0.5415 0.4205 0.058 Uiso 1 1 calc R . . C13 C 0.9688(14) 0.3709(12) 0.4440(3) 0.044(3) Uani 1 1 d . . . C14 C 1.0694(14) 0.3209(15) 0.4180(3) 0.051(4) Uani 1 1 d . . . H14 H 1.1135 0.3718 0.3993 0.062 Uiso 1 1 calc R . . C15 C 1.1084(13) 0.1967(14) 0.4187(3) 0.045(3) Uani 1 1 d . . . C16 C 1.0371(14) 0.1254(13) 0.4456(3) 0.047(3) Uani 1 1 d . . . H16 H 1.0605 0.0409 0.4465 0.057 Uiso 1 1 calc R . . C17 C 0.9338(15) 0.1727(13) 0.4710(3) 0.047(3) Uani 1 1 d . . . H17 H 0.8845 0.1196 0.4884 0.056 Uiso 1 1 calc R . . C18 C 0.8994(13) 0.2961(12) 0.4720(3) 0.038(3) Uani 1 1 d . . . C19 C 1.2254(15) 0.1453(14) 0.3932(3) 0.059(4) Uani 1 1 d . . . H19A H 1.3019 0.0960 0.4083 0.071 Uiso 1 1 calc R . . H19B H 1.2840 0.2124 0.3813 0.071 Uiso 1 1 calc R . . C20 C 1.1290(15) -0.0475(14) 0.3669(4) 0.051(4) Uani 1 1 d . . . H20 H 1.1571 -0.0954 0.3885 0.061 Uiso 1 1 calc R . . C21 C 1.0977(14) 0.1069(12) 0.3273(3) 0.040(3) Uani 1 1 d . . . H21 H 1.1002 0.1874 0.3175 0.048 Uiso 1 1 calc R . . C22 C 1.0401(14) 0.0068(14) 0.3097(4) 0.050(3) Uani 1 1 d . . . H22 H 0.9960 0.0023 0.2846 0.060 Uiso 1 1 calc R . . C23 C 1.017(2) -0.2159(13) 0.3257(5) 0.099(7) Uani 1 1 d . . . H23A H 1.0831 -0.2705 0.3413 0.149 Uiso 1 1 calc R . . H23B H 1.0360 -0.2312 0.2988 0.149 Uiso 1 1 calc R . . H23C H 0.9061 -0.2305 0.3309 0.149 Uiso 1 1 calc R . . C24 C 0.6591(14) 0.7266(11) 0.4696(3) 0.041(3) Uani 1 1 d . . . H24A H 0.6528 0.8151 0.4745 0.049 Uiso 1 1 calc R . . H24B H 0.5764 0.7051 0.4505 0.049 Uiso 1 1 calc R . . C25 C 0.5457(14) 0.7030(11) 0.5309(3) 0.040(3) Uani 1 1 d . . . H25 H 0.5061 0.7831 0.5271 0.048 Uiso 1 1 calc R . . C26 C 0.5024(12) 0.6405(10) 0.5656(3) 0.029(3) Uani 1 1 d . . . C27 C 0.4071(12) 0.7047(11) 0.5905(3) 0.040(3) Uani 1 1 d . . . H27 H 0.3767 0.7858 0.5845 0.048 Uiso 1 1 calc R . . C28 C 0.3564(13) 0.6531(12) 0.6237(3) 0.041(3) Uani 1 1 d . . . C29 C 0.4064(14) 0.5312(11) 0.6314(3) 0.039(3) Uani 1 1 d . . . H29 H 0.3716 0.4925 0.6538 0.047 Uiso 1 1 calc R . . C30 C 0.5024(14) 0.4680(10) 0.6078(3) 0.037(3) Uani 1 1 d . . . H30 H 0.5348 0.3875 0.6140 0.045 Uiso 1 1 calc R . . C31 C 0.5531(13) 0.5239(11) 0.5738(3) 0.036(3) Uani 1 1 d . . . C32 C 0.2515(12) 0.7170(12) 0.6497(3) 0.039(3) Uani 1 1 d . . . H32A H 0.1500 0.6728 0.6504 0.047 Uiso 1 1 calc R . . H32B H 0.2297 0.7995 0.6395 0.047 Uiso 1 1 calc R . . C33 C 0.4353(15) 0.7965(12) 0.6993(4) 0.052(4) Uani 1 1 d . . . H33 H 0.4899 0.8506 0.6832 0.063 Uiso 1 1 calc R . . C34 C 0.2678(16) 0.6625(14) 0.7202(4) 0.061(4) Uani 1 1 d . . . H34 H 0.1843 0.6051 0.7210 0.073 Uiso 1 1 calc R . . C35 C 0.3643(17) 0.6975(15) 0.7491(4) 0.063(4) Uani 1 1 d . . . H35 H 0.3600 0.6696 0.7746 0.076 Uiso 1 1 calc R . . C36 C 0.5965(18) 0.8366(15) 0.7588(4) 0.085(6) Uani 1 1 d . . . H36A H 0.5717 0.8319 0.7858 0.128 Uiso 1 1 calc R . . H36B H 0.6068 0.9221 0.7513 0.128 Uiso 1 1 calc R . . H36C H 0.6958 0.7939 0.7544 0.128 Uiso 1 1 calc R . . P41 P 0.8081(4) 0.9662(3) 0.20440(9) 0.0389(8) Uani 1 1 d . . . F41 F 0.9286(12) 0.9645(9) 0.1723(3) 0.108(4) Uani 1 1 d . . . F42 F 0.9149(14) 1.0593(8) 0.2273(3) 0.117(4) Uani 1 1 d . . . F43 F 0.6879(14) 0.9647(9) 0.2370(3) 0.120(4) Uani 1 1 d . . . F44 F 0.7090(12) 0.8699(7) 0.1816(3) 0.104(4) Uani 1 1 d . . . F45 F 0.7185(9) 1.0767(6) 0.1840(2) 0.059(2) Uani 1 1 d . . . F46 F 0.8976(9) 0.8567(7) 0.2256(2) 0.064(2) Uani 1 1 d . . . P51 P 0.5924(4) 0.9007(3) 0.35903(9) 0.0461(9) Uani 1 1 d . . . F51 F 0.7339(14) 0.8999(19) 0.3836(3) 0.203(9) Uani 1 1 d . . . F52 F 0.5404(12) 1.0298(7) 0.3708(3) 0.111(4) Uani 1 1 d . . . F53 F 0.4445(12) 0.9012(16) 0.3325(3) 0.179(7) Uani 1 1 d . . . F54 F 0.6371(16) 0.7711(9) 0.3459(5) 0.188(8) Uani 1 1 d . . . F55 F 0.6891(11) 0.9475(8) 0.3261(3) 0.092(3) Uani 1 1 d . . . F56 F 0.4843(16) 0.8502(11) 0.3891(4) 0.191(8) Uani 1 1 d . . . O1S O 0.7645(12) 0.1971(11) 0.5601(3) 0.091(4) Uani 1 1 d . . . O2S O 0.421(4) 0.9942(18) 0.4640(6) 0.265(13) 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 0.0406(8) 0.0393(9) 0.0291(7) 0.0074(7) -0.0122(5) -0.0075(8) N11 0.035(6) 0.055(7) 0.035(5) 0.015(5) -0.026(5) -0.022(5) N12 0.031(6) 0.069(9) 0.035(6) -0.002(6) 0.001(4) 0.002(6) N13 0.030(6) 0.037(7) 0.070(8) -0.009(6) 0.001(5) 0.001(5) N14 0.035(6) 0.054(7) 0.025(5) 0.005(5) -0.016(4) -0.016(5) N15 0.026(5) 0.034(6) 0.058(6) -0.007(5) 0.003(5) 0.006(5) N16 0.040(7) 0.044(7) 0.061(7) -0.027(6) -0.010(5) 0.019(6) O11 0.041(5) 0.050(6) 0.025(4) 0.007(4) -0.007(3) 0.004(4) O12 0.047(5) 0.034(5) 0.033(4) -0.001(3) -0.002(4) 0.000(4) C11 0.063(10) 0.061(10) 0.038(7) 0.026(7) -0.024(6) -0.015(8) C12 0.034(7) 0.068(10) 0.042(7) 0.021(7) -0.013(5) -0.018(8) C13 0.046(8) 0.060(10) 0.024(6) 0.003(6) -0.018(5) -0.010(7) C14 0.037(7) 0.095(12) 0.022(6) -0.009(7) -0.005(5) -0.015(8) C15 0.028(7) 0.074(11) 0.033(7) -0.008(7) -0.009(5) -0.002(7) C16 0.043(8) 0.067(10) 0.032(7) -0.006(6) -0.010(6) -0.003(7) C17 0.052(8) 0.058(10) 0.030(7) 0.001(6) -0.005(6) 0.000(7) C18 0.037(7) 0.058(9) 0.019(6) -0.002(6) -0.015(5) -0.007(6) C19 0.040(8) 0.091(12) 0.046(8) -0.030(7) -0.012(6) -0.004(8) C20 0.037(8) 0.047(9) 0.070(10) -0.004(8) 0.027(7) 0.010(7) C21 0.045(8) 0.049(9) 0.027(6) 0.003(6) 0.004(5) -0.002(7) C22 0.036(7) 0.067(10) 0.048(7) -0.009(8) 0.005(5) 0.010(8) C23 0.097(14) 0.039(10) 0.164(17) -0.043(11) 0.060(12) 0.000(9) C24 0.052(8) 0.037(8) 0.033(6) 0.008(5) -0.015(5) -0.014(6) C25 0.039(7) 0.035(8) 0.044(7) 0.006(6) -0.022(6) -0.013(6) C26 0.027(6) 0.020(6) 0.040(6) 0.003(5) -0.014(5) -0.006(5) C27 0.023(6) 0.041(8) 0.054(8) 0.007(6) -0.026(5) -0.003(6) C28 0.032(7) 0.048(9) 0.044(7) -0.004(6) -0.015(5) -0.011(6) C29 0.050(7) 0.047(8) 0.021(5) 0.002(5) -0.001(5) -0.013(6) C30 0.061(8) 0.023(7) 0.027(6) 0.002(5) -0.016(5) 0.005(6) C31 0.030(6) 0.047(8) 0.031(6) 0.002(6) -0.008(5) -0.019(6) C32 0.017(6) 0.053(8) 0.047(7) 0.000(6) -0.002(5) 0.002(6) C33 0.046(8) 0.039(8) 0.071(9) 0.000(7) -0.022(7) 0.011(7) C34 0.042(8) 0.092(12) 0.048(8) -0.007(8) 0.015(6) 0.002(8) C35 0.055(9) 0.098(13) 0.037(7) -0.026(8) 0.016(7) -0.005(9) C36 0.066(11) 0.079(12) 0.109(13) -0.060(10) -0.030(9) 0.012(9) P41 0.0388(18) 0.0311(19) 0.0465(18) 0.0015(14) -0.0031(14) -0.0029(14) F41 0.107(8) 0.105(8) 0.114(7) 0.039(6) 0.059(6) 0.048(6) F42 0.178(11) 0.050(6) 0.117(7) 0.036(5) -0.111(7) -0.042(6) F43 0.159(10) 0.075(7) 0.129(8) 0.037(6) 0.092(8) 0.039(7) F44 0.120(9) 0.042(5) 0.145(9) -0.014(5) -0.081(7) -0.002(5) F45 0.059(5) 0.041(5) 0.076(5) 0.007(4) -0.016(4) 0.004(4) F46 0.058(5) 0.045(5) 0.088(6) 0.014(4) -0.028(4) 0.002(4) P51 0.045(2) 0.046(2) 0.048(2) 0.0130(17) 0.0171(16) 0.0126(17) F51 0.095(9) 0.42(3) 0.088(8) -0.020(11) -0.038(7) 0.107(13) F52 0.115(8) 0.040(5) 0.183(10) 0.000(6) 0.083(8) 0.004(5) F53 0.060(7) 0.34(2) 0.142(10) -0.155(12) -0.004(6) -0.009(9) F54 0.177(13) 0.057(7) 0.339(19) 0.012(9) 0.204(14) 0.017(7) F55 0.087(7) 0.093(7) 0.100(6) 0.047(5) 0.056(5) 0.038(5) F56 0.207(14) 0.139(11) 0.238(14) 0.120(10) 0.192(12) 0.115(10) O1S 0.073(8) 0.108(9) 0.094(8) 0.051(7) 0.031(6) 0.023(7) O2S 0.40(4) 0.150(19) 0.24(2) 0.022(16) -0.12(2) -0.09(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 Cu1 O12 1.911(7) . ? Cu1 O11 1.917(8) . ? Cu1 N14 1.918(11) . ? Cu1 N11 1.931(10) . ? N11 C12 1.312(16) . ? N11 C11 1.497(16) . ? N12 C20 1.291(16) . ? N12 C21 1.396(13) . ? N12 C19 1.485(14) . ? N13 C20 1.336(16) . ? N13 C22 1.369(16) . ? N13 C23 1.490(17) . ? N14 C25 1.283(14) . ? N14 C24 1.475(13) . ? N15 C33 1.300(15) . ? N15 C34 1.388(15) . ? N15 C32 1.482(13) . ? N16 C33 1.322(15) . ? N16 C35 1.344(17) . ? N16 C36 1.488(16) . ? O11 C18 1.325(13) . ? O12 C31 1.339(13) . ? C11 C24 1.495(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.442(18) . ? C12 H12 0.9500 . ? C13 C14 1.381(17) . ? C13 C18 1.423(16) . ? C14 C15 1.404(18) . ? C14 H14 0.9500 . ? C15 C16 1.382(17) . ? C15 C19 1.468(16) . ? C16 C17 1.371(16) . ? C16 H16 0.9500 . ? C17 C18 1.388(17) . ? C17 H17 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20 0.9500 . ? C21 C22 1.350(17) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.456(15) . ? C25 H25 0.9500 . ? C26 C31 1.381(15) . ? C26 C27 1.400(15) . ? C27 C28 1.377(15) . ? C27 H27 0.9500 . ? C28 C29 1.429(17) . ? C28 C32 1.471(15) . ? C29 C30 1.369(16) . ? C29 H29 0.9500 . ? C30 C31 1.420(15) . ? C30 H30 0.9500 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33 0.9500 . ? C34 C35 1.346(18) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? P41 F41 1.543(9) . ? P41 F43 1.556(9) . ? P41 F44 1.562(8) . ? P41 F42 1.577(8) . ? P41 F45 1.594(7) . ? P41 F46 1.599(7) . ? P51 F51 1.462(11) . ? P51 F56 1.524(9) . ? P51 F55 1.527(8) . ? P51 F52 1.546(9) . ? P51 F53 1.547(11) . ? P51 F54 1.548(11) . ? 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 O12 Cu1 O11 89.2(3) . . ? O12 Cu1 N14 94.0(4) . . ? O11 Cu1 N14 171.3(3) . . ? O12 Cu1 N11 171.1(3) . . ? O11 Cu1 N11 93.4(4) . . ? N14 Cu1 N11 84.7(4) . . ? C12 N11 C11 120.5(11) . . ? C12 N11 Cu1 125.7(9) . . ? C11 N11 Cu1 113.6(9) . . ? C20 N12 C21 110.3(11) . . ? C20 N12 C19 123.4(12) . . ? C21 N12 C19 126.3(12) . . ? C20 N13 C22 110.0(11) . . ? C20 N13 C23 126.2(14) . . ? C22 N13 C23 123.5(13) . . ? C25 N14 C24 120.8(11) . . ? C25 N14 Cu1 126.8(8) . . ? C24 N14 Cu1 112.3(8) . . ? C33 N15 C34 108.9(11) . . ? C33 N15 C32 125.3(11) . . ? C34 N15 C32 125.7(11) . . ? C33 N16 C35 108.4(11) . . ? C33 N16 C36 126.8(13) . . ? C35 N16 C36 124.9(13) . . ? C18 O11 Cu1 128.4(7) . . ? C31 O12 Cu1 125.3(7) . . ? C24 C11 N11 106.3(10) . . ? C24 C11 H11A 110.5 . . ? N11 C11 H11A 110.5 . . ? C24 C11 H11B 110.5 . . ? N11 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? N11 C12 C13 126.0(11) . . ? N11 C12 H12 117.0 . . ? C13 C12 H12 117.0 . . ? C14 C13 C18 120.2(13) . . ? C14 C13 C12 116.9(12) . . ? C18 C13 C12 122.9(12) . . ? C13 C14 C15 121.7(12) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 117.1(12) . . ? C16 C15 C19 121.0(14) . . ? C14 C15 C19 121.9(13) . . ? C17 C16 C15 122.1(14) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 121.7(12) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? O11 C18 C17 119.6(11) . . ? O11 C18 C13 123.2(12) . . ? C17 C18 C13 117.1(12) . . ? C15 C19 N12 112.5(10) . . ? C15 C19 H19A 109.1 . . ? N12 C19 H19A 109.1 . . ? C15 C19 H19B 109.1 . . ? N12 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? N12 C20 N13 107.4(13) . . ? N12 C20 H20 126.3 . . ? N13 C20 H20 126.3 . . ? C22 C21 N12 105.9(11) . . ? C22 C21 H21 127.1 . . ? N12 C21 H21 127.1 . . ? C21 C22 N13 106.3(11) . . ? C21 C22 H22 126.8 . . ? N13 C22 H22 126.8 . . ? N13 C23 H23A 109.5 . . ? N13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N14 C24 C11 109.8(10) . . ? N14 C24 H24A 109.7 . . ? C11 C24 H24A 109.7 . . ? N14 C24 H24B 109.7 . . ? C11 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? N14 C25 C26 125.4(11) . . ? N14 C25 H25 117.3 . . ? C26 C25 H25 117.3 . . ? C31 C26 C27 121.2(10) . . ? C31 C26 C25 122.0(11) . . ? C27 C26 C25 116.8(11) . . ? C28 C27 C26 121.5(11) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C27 C28 C29 116.7(11) . . ? C27 C28 C32 122.5(12) . . ? C29 C28 C32 120.7(11) . . ? C30 C29 C28 122.6(10) . . ? C30 C29 H29 118.7 . . ? C28 C29 H29 118.7 . . ? C29 C30 C31 119.3(11) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? O12 C31 C26 126.5(10) . . ? O12 C31 C30 114.9(11) . . ? C26 C31 C30 118.7(11) . . ? C28 C32 N15 113.7(9) . . ? C28 C32 H32A 108.8 . . ? N15 C32 H32A 108.8 . . ? C28 C32 H32B 108.8 . . ? N15 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? N15 C33 N16 109.1(13) . . ? N15 C33 H33 125.5 . . ? N16 C33 H33 125.5 . . ? C35 C34 N15 105.1(13) . . ? C35 C34 H34 127.4 . . ? N15 C34 H34 127.4 . . ? N16 C35 C34 108.5(13) . . ? N16 C35 H35 125.8 . . ? C34 C35 H35 125.8 . . ? N16 C36 H36A 109.5 . . ? N16 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N16 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? F41 P41 F43 178.6(5) . . ? F41 P41 F44 88.5(6) . . ? F43 P41 F44 91.0(7) . . ? F41 P41 F42 89.9(7) . . ? F43 P41 F42 90.5(7) . . ? F44 P41 F42 177.3(6) . . ? F41 P41 F45 89.9(5) . . ? F43 P41 F45 91.5(5) . . ? F44 P41 F45 92.3(4) . . ? F42 P41 F45 89.9(4) . . ? F41 P41 F46 91.0(5) . . ? F43 P41 F46 87.7(5) . . ? F44 P41 F46 88.6(4) . . ? F42 P41 F46 89.3(4) . . ? F45 P41 F46 178.8(4) . . ? F51 P51 F56 95.0(9) . . ? F51 P51 F55 90.1(7) . . ? F56 P51 F55 174.6(9) . . ? F51 P51 F52 94.7(9) . . ? F56 P51 F52 88.0(6) . . ? F55 P51 F52 93.3(5) . . ? F51 P51 F53 179.1(7) . . ? F56 P51 F53 85.8(9) . . ? F55 P51 F53 89.1(7) . . ? F52 P51 F53 85.7(7) . . ? F51 P51 F54 88.1(10) . . ? F56 P51 F54 91.7(6) . . ? F55 P51 F54 86.7(5) . . ? F52 P51 F54 177.1(9) . . ? F53 P51 F54 91.4(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Cu1 N11 C12 -3.1(9) . . . . ? N14 Cu1 N11 C12 -174.5(9) . . . . ? O11 Cu1 N11 C11 -178.9(7) . . . . ? N14 Cu1 N11 C11 9.6(7) . . . . ? O12 Cu1 N14 C25 0.6(9) . . . . ? N11 Cu1 N14 C25 -170.6(9) . . . . ? O12 Cu1 N14 C24 -175.6(7) . . . . ? N11 Cu1 N14 C24 13.3(7) . . . . ? O12 Cu1 O11 C18 -172.9(8) . . . . ? N11 Cu1 O11 C18 -1.4(9) . . . . ? O11 Cu1 O12 C31 -171.4(8) . . . . ? N14 Cu1 O12 C31 0.5(8) . . . . ? C12 N11 C11 C24 154.7(10) . . . . ? Cu1 N11 C11 C24 -29.2(10) . . . . ? C11 N11 C12 C13 179.3(10) . . . . ? Cu1 N11 C12 C13 3.7(16) . . . . ? N11 C12 C13 C14 178.5(10) . . . . ? N11 C12 C13 C18 0.6(18) . . . . ? C18 C13 C14 C15 -1.0(17) . . . . ? C12 C13 C14 C15 -179.0(10) . . . . ? C13 C14 C15 C16 2.3(17) . . . . ? C13 C14 C15 C19 -174.8(10) . . . . ? C14 C15 C16 C17 -0.6(17) . . . . ? C19 C15 C16 C17 176.5(11) . . . . ? C15 C16 C17 C18 -2.4(18) . . . . ? Cu1 O11 C18 C17 -175.9(8) . . . . ? Cu1 O11 C18 C13 5.4(14) . . . . ? C16 C17 C18 O11 -175.2(10) . . . . ? C16 C17 C18 C13 3.6(17) . . . . ? C14 C13 C18 O11 176.8(10) . . . . ? C12 C13 C18 O11 -5.4(16) . . . . ? C14 C13 C18 C17 -1.9(16) . . . . ? C12 C13 C18 C17 175.9(10) . . . . ? C16 C15 C19 N12 74.5(15) . . . . ? C14 C15 C19 N12 -108.6(14) . . . . ? C20 N12 C19 C15 -89.5(15) . . . . ? C21 N12 C19 C15 89.1(15) . . . . ? C21 N12 C20 N13 -0.7(13) . . . . ? C19 N12 C20 N13 178.1(10) . . . . ? C22 N13 C20 N12 1.7(14) . . . . ? C23 N13 C20 N12 175.7(11) . . . . ? C20 N12 C21 C22 -0.5(13) . . . . ? C19 N12 C21 C22 -179.3(10) . . . . ? N12 C21 C22 N13 1.5(12) . . . . ? C20 N13 C22 C21 -2.0(13) . . . . ? C23 N13 C22 C21 -176.3(11) . . . . ? C25 N14 C24 C11 150.3(10) . . . . ? Cu1 N14 C24 C11 -33.3(11) . . . . ? N11 C11 C24 N14 39.0(12) . . . . ? C24 N14 C25 C26 175.1(9) . . . . ? Cu1 N14 C25 C26 -0.7(16) . . . . ? N14 C25 C26 C31 -0.2(16) . . . . ? N14 C25 C26 C27 179.3(10) . . . . ? C31 C26 C27 C28 -1.9(16) . . . . ? C25 C26 C27 C28 178.5(9) . . . . ? C26 C27 C28 C29 0.2(15) . . . . ? C26 C27 C28 C32 -177.6(10) . . . . ? C27 C28 C29 C30 1.3(16) . . . . ? C32 C28 C29 C30 179.2(10) . . . . ? C28 C29 C30 C31 -1.1(17) . . . . ? Cu1 O12 C31 C26 -1.4(14) . . . . ? Cu1 O12 C31 C30 178.4(7) . . . . ? C27 C26 C31 O12 -178.1(9) . . . . ? C25 C26 C31 O12 1.4(16) . . . . ? C27 C26 C31 C30 2.1(15) . . . . ? C25 C26 C31 C30 -178.4(9) . . . . ? C29 C30 C31 O12 179.6(9) . . . . ? C29 C30 C31 C26 -0.6(16) . . . . ? C27 C28 C32 N15 -123.3(11) . . . . ? C29 C28 C32 N15 58.9(14) . . . . ? C33 N15 C32 C28 69.6(15) . . . . ? C34 N15 C32 C28 -106.2(13) . . . . ? C34 N15 C33 N16 0.3(14) . . . . ? C32 N15 C33 N16 -176.1(10) . . . . ? C35 N16 C33 N15 -1.0(14) . . . . ? C36 N16 C33 N15 178.7(11) . . . . ? C33 N15 C34 C35 0.4(15) . . . . ? C32 N15 C34 C35 176.8(11) . . . . ? C33 N16 C35 C34 1.2(15) . . . . ? C36 N16 C35 C34 -178.4(12) . . . . ? N15 C34 C35 N16 -1.0(15) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.896 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.144