Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prof. Matthias Tamm' _publ_contact_author_email MATTHIAS.TAMM@TU-BS.DE loop_ _publ_author_name 'Matthias Tamm' 'Lyndal M. R. Hill' 'Peter G. Jones' 'Dejan Petrovic' 'William Tolman' data_dpet17a _database_code_depnum_ccdc_archive 'CCDC 663318' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H44 Cl Cu N6' _chemical_formula_weight 515.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.7423(12) _cell_length_b 9.2407(6) _cell_length_c 18.3128(14) _cell_angle_alpha 90.00 _cell_angle_beta 107.664(3) _cell_angle_gamma 90.00 _cell_volume 2699.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 6881 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 30.41 _exptl_crystal_description fragment _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7697 _exptl_absorpt_correction_T_max 0.8730 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 1000 CCD' _diffrn_measurement_method '\w- & \f-scan' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56246 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 30.53 _reflns_number_total 8246 _reflns_number_gt 6538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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 'Siemens XP' _computing_publication_material SHELXL-97 _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^)+(0.0394P)^2^+1.1240P] 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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8246 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.949046(10) 0.177318(19) 0.159309(9) 0.02131(5) Uani 1 1 d . . . Cl1 Cl 1.02631(2) 0.04640(4) 0.25149(2) 0.02708(8) Uani 1 1 d . . . N1 N 0.98405(7) 0.30271(13) 0.08131(7) 0.0211(2) Uani 1 1 d . . . N2 N 0.83535(7) 0.26443(14) 0.11338(6) 0.0201(2) Uani 1 1 d . . . N3 N 1.10262(7) 0.46080(14) 0.14239(6) 0.0209(2) Uani 1 1 d . . . N4 N 1.12387(7) 0.27036(14) 0.07864(6) 0.0208(2) Uani 1 1 d . . . N5 N 0.68418(7) 0.27586(14) 0.08853(6) 0.0200(2) Uani 1 1 d . . . N6 N 0.76525(7) 0.26070(14) 0.20868(6) 0.0199(2) Uani 1 1 d . . . C1 C 0.91830(8) 0.41217(17) 0.05489(8) 0.0249(3) Uani 1 1 d . . . H1A H 0.9213 0.4568 0.0067 0.030 Uiso 1 1 calc R . . H1B H 0.9253 0.4892 0.0939 0.030 Uiso 1 1 calc R . . C2 C 0.83443(8) 0.33668(16) 0.04180(8) 0.0221(3) Uani 1 1 d . . . H2A H 0.7883 0.4082 0.0270 0.027 Uiso 1 1 calc R . . H2B H 0.8256 0.2648 0.0000 0.027 Uiso 1 1 calc R . . C3 C 1.06339(8) 0.34402(15) 0.09975(7) 0.0186(2) Uani 1 1 d . . . C4 C 1.18818(8) 0.45900(17) 0.14686(8) 0.0236(3) Uani 1 1 d . . . C5 C 1.20101(8) 0.34194(17) 0.10830(8) 0.0230(3) Uani 1 1 d . . . C6 C 1.24708(10) 0.5793(2) 0.18135(10) 0.0349(4) Uani 1 1 d . . . H6A H 1.3033 0.5553 0.1791 0.052 Uiso 1 1 calc R . . H6B H 1.2489 0.5927 0.2349 0.052 Uiso 1 1 calc R . . H6C H 1.2278 0.6687 0.1527 0.052 Uiso 1 1 calc R . . C7 C 1.28035(9) 0.2967(2) 0.09305(10) 0.0332(4) Uani 1 1 d . . . H7A H 1.2761 0.3172 0.0395 0.050 Uiso 1 1 calc R . . H7B H 1.2892 0.1928 0.1028 0.050 Uiso 1 1 calc R . . H7C H 1.3277 0.3506 0.1268 0.050 Uiso 1 1 calc R . . C8 C 1.06902(10) 0.52254(18) 0.20139(8) 0.0268(3) Uani 1 1 d . . . H8 H 1.0094 0.4897 0.1885 0.032 Uiso 1 1 calc R . . C9 C 1.11473(12) 0.4584(2) 0.27979(9) 0.0387(4) Uani 1 1 d . . . H9A H 1.1121 0.3525 0.2768 0.058 Uiso 1 1 calc R . . H9B H 1.0880 0.4919 0.3175 0.058 Uiso 1 1 calc R . . H9C H 1.1735 0.4895 0.2955 0.058 Uiso 1 1 calc R . . C10 C 1.06697(14) 0.6862(2) 0.20002(13) 0.0466(5) Uani 1 1 d . . . H10A H 1.1244 0.7237 0.2183 0.070 Uiso 1 1 calc R . . H10B H 1.0351 0.7212 0.2334 0.070 Uiso 1 1 calc R . . H10C H 1.0401 0.7197 0.1475 0.070 Uiso 1 1 calc R . . C11 C 1.10316(9) 0.13695(18) 0.03314(8) 0.0267(3) Uani 1 1 d . . . H11 H 1.0406 0.1324 0.0133 0.032 Uiso 1 1 calc R . . C12 C 1.13427(13) 0.1378(2) -0.03698(10) 0.0421(4) Uani 1 1 d . . . H12A H 1.1213 0.2314 -0.0631 0.063 Uiso 1 1 calc R . . H12B H 1.1065 0.0604 -0.0721 0.063 Uiso 1 1 calc R . . H12C H 1.1950 0.1222 -0.0208 0.063 Uiso 1 1 calc R . . C13 C 1.13113(12) 0.00413(19) 0.08338(11) 0.0370(4) Uani 1 1 d . . . H13A H 1.1925 0.0003 0.1015 0.056 Uiso 1 1 calc R . . H13B H 1.1094 -0.0831 0.0536 0.056 Uiso 1 1 calc R . . H13C H 1.1095 0.0096 0.1274 0.056 Uiso 1 1 calc R . . C14 C 0.76675(8) 0.26457(15) 0.13397(7) 0.0178(2) Uani 1 1 d . . . C15 C 0.63250(8) 0.28842(16) 0.13681(8) 0.0216(3) Uani 1 1 d . . . C16 C 0.68224(9) 0.28275(16) 0.20970(8) 0.0223(3) Uani 1 1 d . . . C17 C 0.54040(9) 0.3164(2) 0.10783(10) 0.0334(4) Uani 1 1 d . . . H17A H 0.5193 0.3375 0.1511 0.050 Uiso 1 1 calc R . . H17B H 0.5118 0.2307 0.0805 0.050 Uiso 1 1 calc R . . H17C H 0.5296 0.3993 0.0728 0.050 Uiso 1 1 calc R . . C18 C 0.65875(10) 0.3046(2) 0.28140(9) 0.0323(3) Uani 1 1 d . . . H18A H 0.6006 0.3381 0.2682 0.049 Uiso 1 1 calc R . . H18B H 0.6958 0.3772 0.3136 0.049 Uiso 1 1 calc R . . H18C H 0.6645 0.2130 0.3094 0.049 Uiso 1 1 calc R . . C19 C 0.65670(8) 0.21601(17) 0.00973(7) 0.0225(3) Uani 1 1 d . . . H19 H 0.7085 0.2026 -0.0060 0.027 Uiso 1 1 calc R . . C20 C 0.61779(12) 0.0668(2) 0.00815(10) 0.0384(4) Uani 1 1 d . . . H20A H 0.6571 0.0035 0.0450 0.058 Uiso 1 1 calc R . . H20B H 0.6054 0.0257 -0.0434 0.058 Uiso 1 1 calc R . . H20C H 0.5658 0.0751 0.0219 0.058 Uiso 1 1 calc R . . C21 C 0.60071(11) 0.3200(2) -0.04764(10) 0.0407(4) Uani 1 1 d . . . H21A H 0.5453 0.3236 -0.0399 0.061 Uiso 1 1 calc R . . H21B H 0.5949 0.2867 -0.0998 0.061 Uiso 1 1 calc R . . H21C H 0.6258 0.4168 -0.0402 0.061 Uiso 1 1 calc R . . C22 C 0.84287(9) 0.26339(17) 0.27357(8) 0.0243(3) Uani 1 1 d . . . H22 H 0.8869 0.2161 0.2551 0.029 Uiso 1 1 calc R . . C23 C 0.87183(12) 0.4178(2) 0.29396(10) 0.0389(4) Uani 1 1 d . . . H23A H 0.8805 0.4654 0.2491 0.058 Uiso 1 1 calc R . . H23B H 0.9246 0.4173 0.3360 0.058 Uiso 1 1 calc R . . H23C H 0.8291 0.4705 0.3099 0.058 Uiso 1 1 calc R . . C24 C 0.83778(11) 0.1758(2) 0.34255(9) 0.0345(4) Uani 1 1 d . . . H24A H 0.8070 0.2312 0.3710 0.052 Uiso 1 1 calc R . . H24B H 0.8945 0.1555 0.3761 0.052 Uiso 1 1 calc R . . H24C H 0.8085 0.0845 0.3250 0.052 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 0.02129(9) 0.02107(10) 0.02041(9) 0.00122(6) 0.00460(6) 0.00184(6) Cl1 0.02293(16) 0.02724(19) 0.02809(17) 0.00542(13) 0.00328(12) 0.00317(12) N1 0.0150(5) 0.0260(6) 0.0223(5) 0.0028(4) 0.0058(4) -0.0007(4) N2 0.0162(5) 0.0264(6) 0.0180(5) 0.0026(4) 0.0054(4) 0.0015(4) N3 0.0181(5) 0.0263(6) 0.0185(5) -0.0012(4) 0.0057(4) -0.0013(4) N4 0.0173(5) 0.0256(6) 0.0203(5) -0.0007(4) 0.0068(4) 0.0001(4) N5 0.0151(5) 0.0269(6) 0.0179(5) -0.0026(4) 0.0048(4) 0.0006(4) N6 0.0176(5) 0.0263(6) 0.0156(5) -0.0007(4) 0.0049(4) 0.0029(4) C1 0.0174(6) 0.0292(8) 0.0273(7) 0.0088(6) 0.0057(5) 0.0014(5) C2 0.0163(6) 0.0319(8) 0.0183(6) 0.0039(5) 0.0054(5) 0.0001(5) C3 0.0174(6) 0.0237(7) 0.0154(5) 0.0030(4) 0.0061(4) 0.0008(5) C4 0.0164(6) 0.0308(8) 0.0223(6) 0.0023(5) 0.0039(5) -0.0028(5) C5 0.0151(6) 0.0320(8) 0.0219(6) 0.0047(5) 0.0055(5) 0.0010(5) C6 0.0239(7) 0.0409(10) 0.0366(8) -0.0035(7) 0.0042(6) -0.0103(6) C7 0.0196(7) 0.0420(10) 0.0402(9) 0.0052(7) 0.0123(6) 0.0039(6) C8 0.0273(7) 0.0315(8) 0.0227(7) -0.0047(6) 0.0092(5) 0.0021(6) C9 0.0466(10) 0.0490(11) 0.0201(7) -0.0028(7) 0.0093(7) -0.0069(8) C10 0.0482(11) 0.0334(10) 0.0585(12) -0.0077(8) 0.0165(9) 0.0066(8) C11 0.0242(7) 0.0306(8) 0.0253(7) -0.0067(6) 0.0076(5) 0.0004(6) C12 0.0492(11) 0.0521(12) 0.0275(8) -0.0093(7) 0.0156(7) 0.0056(9) C13 0.0426(9) 0.0270(9) 0.0415(9) -0.0035(7) 0.0129(7) 0.0011(7) C14 0.0172(6) 0.0196(7) 0.0164(5) -0.0005(4) 0.0046(4) 0.0007(4) C15 0.0167(6) 0.0259(7) 0.0237(6) -0.0020(5) 0.0082(5) 0.0012(5) C16 0.0206(6) 0.0256(7) 0.0230(6) -0.0005(5) 0.0101(5) 0.0037(5) C17 0.0174(6) 0.0491(11) 0.0334(8) -0.0065(7) 0.0076(6) 0.0047(6) C18 0.0282(7) 0.0479(10) 0.0250(7) -0.0023(6) 0.0143(6) 0.0060(7) C19 0.0191(6) 0.0328(8) 0.0144(6) -0.0015(5) 0.0033(5) -0.0037(5) C20 0.0463(10) 0.0416(10) 0.0304(8) -0.0122(7) 0.0165(7) -0.0164(8) C21 0.0357(9) 0.0561(12) 0.0244(7) 0.0090(7) 0.0002(6) 0.0056(8) C22 0.0208(6) 0.0335(8) 0.0166(6) -0.0021(5) 0.0026(5) 0.0060(5) C23 0.0390(9) 0.0435(11) 0.0303(8) -0.0084(7) 0.0048(7) -0.0115(8) C24 0.0390(9) 0.0402(10) 0.0212(7) 0.0052(6) 0.0044(6) 0.0110(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 N2 2.0019(11) . ? Cu1 N1 2.0577(12) . ? Cu1 Cl1 2.1590(4) . ? N1 C3 1.3237(17) . ? N1 C1 1.4648(18) . ? N2 C14 1.3130(16) . ? N2 C2 1.4670(17) . ? N3 C3 1.3764(18) . ? N3 C4 1.4099(17) . ? N3 C8 1.4760(18) . ? N4 C3 1.3694(17) . ? N4 C5 1.4054(18) . ? N4 C11 1.4693(19) . ? N5 C14 1.3843(16) . ? N5 C15 1.4172(17) . ? N5 C19 1.4822(17) . ? N6 C14 1.3764(16) . ? N6 C16 1.4105(17) . ? N6 C22 1.4711(17) . ? C1 C2 1.5203(19) . ? C4 C5 1.344(2) . ? C4 C6 1.493(2) . ? C5 C7 1.497(2) . ? C8 C10 1.513(3) . ? C8 C9 1.527(2) . ? C11 C13 1.520(2) . ? C11 C12 1.525(2) . ? C15 C16 1.3429(19) . ? C15 C17 1.4932(19) . ? C16 C18 1.4943(19) . ? C19 C21 1.519(2) . ? C19 C20 1.521(2) . ? C22 C23 1.517(2) . ? C22 C24 1.524(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 85.22(5) . . ? N2 Cu1 Cl1 145.24(3) . . ? N1 Cu1 Cl1 128.98(3) . . ? C3 N1 C1 118.72(12) . . ? C3 N1 Cu1 117.42(9) . . ? C1 N1 Cu1 105.92(8) . . ? C14 N2 C2 118.90(11) . . ? C14 N2 Cu1 133.06(9) . . ? C2 N2 Cu1 108.01(8) . . ? C3 N3 C4 108.97(11) . . ? C3 N3 C8 119.75(11) . . ? C4 N3 C8 124.63(12) . . ? C3 N4 C5 109.18(12) . . ? C3 N4 C11 120.64(11) . . ? C5 N4 C11 130.17(12) . . ? C14 N5 C15 108.57(11) . . ? C14 N5 C19 121.03(11) . . ? C15 N5 C19 124.76(11) . . ? C14 N6 C16 108.95(11) . . ? C14 N6 C22 121.63(11) . . ? C16 N6 C22 128.27(11) . . ? N1 C1 C2 107.50(12) . . ? N2 C2 C1 108.01(11) . . ? N1 C3 N4 123.74(13) . . ? N1 C3 N3 129.79(12) . . ? N4 C3 N3 106.47(11) . . ? C5 C4 N3 107.49(12) . . ? C5 C4 C6 129.12(13) . . ? N3 C4 C6 123.02(14) . . ? C4 C5 N4 107.88(12) . . ? C4 C5 C7 127.93(14) . . ? N4 C5 C7 124.05(14) . . ? N3 C8 C10 112.70(14) . . ? N3 C8 C9 110.15(13) . . ? C10 C8 C9 113.97(15) . . ? N4 C11 C13 110.97(12) . . ? N4 C11 C12 113.02(14) . . ? C13 C11 C12 113.12(14) . . ? N2 C14 N6 124.53(12) . . ? N2 C14 N5 128.92(12) . . ? N6 C14 N5 106.47(11) . . ? C16 C15 N5 107.77(11) . . ? C16 C15 C17 128.47(13) . . ? N5 C15 C17 123.54(13) . . ? C15 C16 N6 107.98(12) . . ? C15 C16 C18 128.25(13) . . ? N6 C16 C18 123.66(12) . . ? N5 C19 C21 112.42(13) . . ? N5 C19 C20 111.18(12) . . ? C21 C19 C20 112.91(14) . . ? N6 C22 C23 110.65(13) . . ? N6 C22 C24 113.75(13) . . ? C23 C22 C24 112.93(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C3 152.18(11) . . . . ? Cl1 Cu1 N1 C3 -20.99(13) . . . . ? N2 Cu1 N1 C1 16.87(9) . . . . ? Cl1 Cu1 N1 C1 -156.30(7) . . . . ? N1 Cu1 N2 C14 -168.66(14) . . . . ? Cl1 Cu1 N2 C14 2.00(18) . . . . ? N1 Cu1 N2 C2 13.15(9) . . . . ? Cl1 Cu1 N2 C2 -176.19(7) . . . . ? C3 N1 C1 C2 -177.19(12) . . . . ? Cu1 N1 C1 C2 -42.58(12) . . . . ? C14 N2 C2 C1 141.47(13) . . . . ? Cu1 N2 C2 C1 -40.04(13) . . . . ? N1 C1 C2 N2 56.13(15) . . . . ? C1 N1 C3 N4 -136.50(14) . . . . ? Cu1 N1 C3 N4 93.96(14) . . . . ? C1 N1 C3 N3 44.6(2) . . . . ? Cu1 N1 C3 N3 -84.98(16) . . . . ? C5 N4 C3 N1 -179.21(12) . . . . ? C11 N4 C3 N1 -0.2(2) . . . . ? C5 N4 C3 N3 -0.06(14) . . . . ? C11 N4 C3 N3 178.94(12) . . . . ? C4 N3 C3 N1 179.54(13) . . . . ? C8 N3 C3 N1 26.8(2) . . . . ? C4 N3 C3 N4 0.46(14) . . . . ? C8 N3 C3 N4 -152.24(12) . . . . ? C3 N3 C4 C5 -0.71(15) . . . . ? C8 N3 C4 C5 150.35(14) . . . . ? C3 N3 C4 C6 172.85(13) . . . . ? C8 N3 C4 C6 -36.1(2) . . . . ? N3 C4 C5 N4 0.66(16) . . . . ? C6 C4 C5 N4 -172.38(15) . . . . ? N3 C4 C5 C7 176.55(14) . . . . ? C6 C4 C5 C7 3.5(3) . . . . ? C3 N4 C5 C4 -0.38(16) . . . . ? C11 N4 C5 C4 -179.25(14) . . . . ? C3 N4 C5 C7 -176.47(13) . . . . ? C11 N4 C5 C7 4.7(2) . . . . ? C3 N3 C8 C10 -136.23(15) . . . . ? C4 N3 C8 C10 75.58(19) . . . . ? C3 N3 C8 C9 95.26(16) . . . . ? C4 N3 C8 C9 -52.94(19) . . . . ? C3 N4 C11 C13 -101.96(15) . . . . ? C5 N4 C11 C13 76.80(18) . . . . ? C3 N4 C11 C12 129.75(14) . . . . ? C5 N4 C11 C12 -51.5(2) . . . . ? C2 N2 C14 N6 -150.48(13) . . . . ? Cu1 N2 C14 N6 31.5(2) . . . . ? C2 N2 C14 N5 25.8(2) . . . . ? Cu1 N2 C14 N5 -152.19(12) . . . . ? C16 N6 C14 N2 171.79(14) . . . . ? C22 N6 C14 N2 3.1(2) . . . . ? C16 N6 C14 N5 -5.24(16) . . . . ? C22 N6 C14 N5 -173.88(13) . . . . ? C15 N5 C14 N2 -173.06(14) . . . . ? C19 N5 C14 N2 32.3(2) . . . . ? C15 N5 C14 N6 3.78(16) . . . . ? C19 N5 C14 N6 -150.90(12) . . . . ? C14 N5 C15 C16 -0.87(17) . . . . ? C19 N5 C15 C16 152.64(14) . . . . ? C14 N5 C15 C17 174.14(14) . . . . ? C19 N5 C15 C17 -32.4(2) . . . . ? N5 C15 C16 N6 -2.35(17) . . . . ? C17 C15 C16 N6 -177.04(15) . . . . ? N5 C15 C16 C18 173.92(15) . . . . ? C17 C15 C16 C18 -0.8(3) . . . . ? C14 N6 C16 C15 4.81(17) . . . . ? C22 N6 C16 C15 172.47(14) . . . . ? C14 N6 C16 C18 -171.68(15) . . . . ? C22 N6 C16 C18 -4.0(2) . . . . ? C14 N5 C19 C21 -135.08(14) . . . . ? C15 N5 C19 C21 74.49(18) . . . . ? C14 N5 C19 C20 97.23(16) . . . . ? C15 N5 C19 C20 -53.20(19) . . . . ? C14 N6 C22 C23 85.27(16) . . . . ? C16 N6 C22 C23 -81.00(18) . . . . ? C14 N6 C22 C24 -146.36(14) . . . . ? C16 N6 C22 C24 47.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.485 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.065 # Attachment 'DEAN83.CIF' data_dean83 _database_code_depnum_ccdc_archive 'CCDC 663319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H90 Cu2 F12 N12 O2 P2' _chemical_formula_weight 1284.34 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7395(6) _cell_length_b 25.0543(14) _cell_length_c 13.6929(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.799(4) _cell_angle_gamma 90.00 _cell_volume 2962.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9968 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 0.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8057 _exptl_absorpt_correction_T_max 0.9872 _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 'Bruker APEX2 CCD' _diffrn_measurement_method '\w- and \f-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 50894 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.88 _reflns_number_total 7050 _reflns_number_gt 5296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0425P)^2^+4.0837P] 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 'methyls rigid and others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7050 _refine_ls_number_parameters 377 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.023 _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 Cu Cu 0.58487(4) 0.449429(11) 0.53938(2) 0.02062(9) Uani 1 1 d . . . O O 0.4296(2) 0.47522(7) 0.43428(14) 0.0352(5) Uani 1 1 d D . . H01 H 0.383(4) 0.4588(12) 0.3878(19) 0.045(10) Uiso 1 1 d D . . N1 N 0.5796(3) 0.37443(8) 0.51155(16) 0.0282(5) Uani 1 1 d . . . N2 N 0.7583(3) 0.43118(8) 0.64116(15) 0.0234(4) Uani 1 1 d . . . N3 N 0.3514(3) 0.32098(8) 0.47441(15) 0.0254(5) Uani 1 1 d . A . N4 N 0.4689(2) 0.34033(8) 0.35012(14) 0.0214(4) Uani 1 1 d . . . N5 N 0.7502(2) 0.46153(8) 0.80989(15) 0.0201(4) Uani 1 1 d . . . N6 N 0.8903(2) 0.50635(7) 0.71942(14) 0.0195(4) Uani 1 1 d . . . C1 C 0.7279(3) 0.34931(9) 0.55033(18) 0.0233(5) Uani 1 1 d . . . H1A H 0.8051 0.3565 0.5061 0.028 Uiso 1 1 calc R . . H1B H 0.7151 0.3102 0.5554 0.028 Uiso 1 1 calc R . . C2 C 0.7802(4) 0.37310(10) 0.65117(19) 0.0313(6) Uani 1 1 d . . . H2A H 0.7178 0.3586 0.6997 0.038 Uiso 1 1 calc R . . H2B H 0.8905 0.3646 0.6740 0.038 Uiso 1 1 calc R . . C3 C 0.4752(3) 0.34681(9) 0.44933(17) 0.0222(5) Uani 1 1 d . . . C4 C 0.2680(3) 0.29698(10) 0.39061(18) 0.0259(5) Uani 1 1 d . . . C5 C 0.3418(3) 0.30854(9) 0.31391(17) 0.0220(5) Uani 1 1 d . . . C6 C 0.1250(4) 0.26493(13) 0.3917(2) 0.0441(8) Uani 1 1 d . . . H6A H 0.0393 0.2887 0.4009 0.053 Uiso 1 1 calc R . . H6B H 0.1420 0.2391 0.4460 0.053 Uiso 1 1 calc R . . H6C H 0.0994 0.2459 0.3288 0.053 Uiso 1 1 calc R . . C7 C 0.3043(3) 0.28948(11) 0.20952(19) 0.0321(6) Uani 1 1 d . . . H7A H 0.2232 0.2622 0.2051 0.039 Uiso 1 1 calc R . . H7B H 0.3973 0.2742 0.1886 0.039 Uiso 1 1 calc R . . H7C H 0.2677 0.3196 0.1664 0.039 Uiso 1 1 calc R . . C8 C 0.3261(4) 0.31483(12) 0.57773(19) 0.0383(7) Uani 1 1 d DU . . H8 H 0.3985 0.3402 0.6180 0.046 Uiso 0.742(7) 1 calc PR A 1 H8' H 0.2262 0.2947 0.5658 0.046 Uiso 0.258(7) 1 calc PR A 2 C9 C 0.3774(5) 0.25799(18) 0.6121(3) 0.0326(10) Uani 0.742(7) 1 d PDU A 1 H9A H 0.3825 0.2554 0.6839 0.039 Uiso 0.742(7) 1 calc PR A 1 H9B H 0.4797 0.2505 0.5943 0.039 Uiso 0.742(7) 1 calc PR A 1 H9C H 0.3024 0.2320 0.5799 0.039 Uiso 0.742(7) 1 calc PR A 1 C10 C 0.1714(6) 0.3283(2) 0.5954(3) 0.0532(16) Uani 0.742(7) 1 d PDU A 1 H10A H 0.0974 0.3024 0.5619 0.064 Uiso 0.742(7) 1 calc PR A 1 H10B H 0.1443 0.3641 0.5696 0.064 Uiso 0.742(7) 1 calc PR A 1 H10C H 0.1678 0.3276 0.6666 0.064 Uiso 0.742(7) 1 calc PR A 1 C9' C 0.4102(15) 0.2801(5) 0.6451(10) 0.038(3) Uiso 0.258(7) 1 d PDU A 2 H9'1 H 0.4445 0.2494 0.6097 0.046 Uiso 0.258(7) 1 calc PR A 2 H9'2 H 0.3446 0.2677 0.6925 0.046 Uiso 0.258(7) 1 calc PR A 2 H9'3 H 0.5007 0.2987 0.6804 0.046 Uiso 0.258(7) 1 calc PR A 2 C10' C 0.2650(13) 0.3685(4) 0.6203(8) 0.032(3) Uiso 0.258(7) 1 d PDU A 2 H10D H 0.2101 0.3897 0.5659 0.038 Uiso 0.258(7) 1 calc PR A 2 H10E H 0.3529 0.3889 0.6542 0.038 Uiso 0.258(7) 1 calc PR A 2 H10F H 0.1943 0.3598 0.6671 0.038 Uiso 0.258(7) 1 calc PR A 2 C11 C 0.5855(3) 0.36408(10) 0.29652(19) 0.0251(5) Uani 1 1 d . . . H11 H 0.6476 0.3895 0.3430 0.030 Uiso 1 1 calc R . . C12 C 0.5123(3) 0.39648(11) 0.2077(2) 0.0340(6) Uani 1 1 d . . . H12A H 0.4620 0.3723 0.1563 0.041 Uiso 1 1 calc R . . H12B H 0.5925 0.4171 0.1819 0.041 Uiso 1 1 calc R . . H12C H 0.4351 0.4209 0.2277 0.041 Uiso 1 1 calc R . . C13 C 0.6968(4) 0.32194(11) 0.2702(2) 0.0361(7) Uani 1 1 d . . . H13A H 0.7426 0.3029 0.3302 0.043 Uiso 1 1 calc R . . H13B H 0.7790 0.3391 0.2401 0.043 Uiso 1 1 calc R . . H13C H 0.6407 0.2966 0.2233 0.043 Uiso 1 1 calc R . . C14 C 0.7972(3) 0.46291(9) 0.71982(17) 0.0193(5) Uani 1 1 d . . . C15 C 0.8165(3) 0.50436(9) 0.86704(17) 0.0214(5) Uani 1 1 d . . . C16 C 0.9023(3) 0.53227(9) 0.81070(17) 0.0206(5) Uani 1 1 d . . . C17 C 0.7928(4) 0.51593(11) 0.97054(19) 0.0321(6) Uani 1 1 d . . . H17A H 0.8674 0.5430 0.9991 0.039 Uiso 1 1 calc R . . H17B H 0.8081 0.4832 1.0099 0.039 Uiso 1 1 calc R . . H17C H 0.6873 0.5292 0.9705 0.039 Uiso 1 1 calc R . . C18 C 0.9905(3) 0.58268(10) 0.8356(2) 0.0304(6) Uani 1 1 d . . . H18A H 0.9836 0.5929 0.9038 0.037 Uiso 1 1 calc R . . H18B H 0.9465 0.6111 0.7907 0.037 Uiso 1 1 calc R . . H18C H 1.0993 0.5772 0.8285 0.037 Uiso 1 1 calc R . . C19 C 0.6245(3) 0.42587(10) 0.8316(2) 0.0275(6) Uani 1 1 d . . . H19 H 0.5938 0.4043 0.7703 0.033 Uiso 1 1 calc R . . C20 C 0.6794(4) 0.38628(15) 0.9117(3) 0.0583(11) Uani 1 1 d . . . H20A H 0.7726 0.3683 0.8967 0.070 Uiso 1 1 calc R . . H20B H 0.5980 0.3598 0.9157 0.070 Uiso 1 1 calc R . . H20C H 0.7036 0.4049 0.9751 0.070 Uiso 1 1 calc R . . C21 C 0.4832(4) 0.45668(13) 0.8462(3) 0.0547(10) Uani 1 1 d . . . H21A H 0.5026 0.4756 0.9096 0.066 Uiso 1 1 calc R . . H21B H 0.3960 0.4321 0.8462 0.066 Uiso 1 1 calc R . . H21C H 0.4584 0.4826 0.7925 0.066 Uiso 1 1 calc R . . C22 C 0.9817(3) 0.51531(10) 0.63888(18) 0.0252(5) Uani 1 1 d . . . H22 H 0.9374 0.4913 0.5833 0.030 Uiso 1 1 calc R . . C23 C 1.1479(4) 0.49782(13) 0.6705(2) 0.0400(7) Uani 1 1 d . . . H23A H 1.1969 0.5209 0.7241 0.048 Uiso 1 1 calc R . . H23B H 1.2045 0.5005 0.6142 0.048 Uiso 1 1 calc R . . H23C H 1.1497 0.4608 0.6936 0.048 Uiso 1 1 calc R . . C24 C 0.9684(4) 0.57178(12) 0.5990(2) 0.0387(7) Uani 1 1 d . . . H24A H 0.8591 0.5822 0.5860 0.046 Uiso 1 1 calc R . . H24B H 1.0126 0.5735 0.5375 0.046 Uiso 1 1 calc R . . H24C H 1.0249 0.5961 0.6477 0.046 Uiso 1 1 calc R . . P P 0.67486(9) 0.17227(3) 0.40735(5) 0.02641(16) Uani 1 1 d . . . F1 F 0.5460(3) 0.16479(9) 0.47493(17) 0.0698(7) Uani 1 1 d . . . F2 F 0.7951(3) 0.14142(7) 0.48910(13) 0.0552(6) Uani 1 1 d . . . F3 F 0.8106(2) 0.17904(9) 0.34305(14) 0.0532(5) Uani 1 1 d . . . F4 F 0.5604(2) 0.20224(7) 0.32542(14) 0.0472(5) Uani 1 1 d . . . F5 F 0.7235(3) 0.22732(7) 0.46100(13) 0.0586(6) Uani 1 1 d . . . F6 F 0.6276(2) 0.11683(6) 0.35406(13) 0.0439(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.02637(16) 0.01287(14) 0.01929(15) -0.00306(11) -0.00718(11) 0.00185(12) O 0.0458(12) 0.0165(9) 0.0338(11) -0.0087(8) -0.0243(9) 0.0089(8) N1 0.0331(12) 0.0148(10) 0.0306(12) -0.0070(8) -0.0146(10) 0.0045(9) N2 0.0298(11) 0.0145(9) 0.0216(10) -0.0042(8) -0.0095(9) 0.0032(8) N3 0.0375(13) 0.0213(10) 0.0153(10) 0.0025(8) -0.0031(9) -0.0046(9) N4 0.0238(11) 0.0187(10) 0.0199(10) -0.0055(8) -0.0021(8) -0.0004(8) N5 0.0200(10) 0.0168(9) 0.0227(10) -0.0020(7) 0.0012(8) -0.0020(8) N6 0.0260(11) 0.0160(9) 0.0156(9) -0.0010(7) -0.0002(8) -0.0021(8) C1 0.0285(13) 0.0156(11) 0.0235(12) -0.0023(9) -0.0032(10) 0.0029(10) C2 0.0451(17) 0.0163(12) 0.0264(13) -0.0036(10) -0.0138(12) 0.0075(11) C3 0.0327(14) 0.0103(10) 0.0205(11) -0.0008(9) -0.0055(10) 0.0034(9) C4 0.0316(14) 0.0209(12) 0.0226(12) 0.0017(10) -0.0044(10) -0.0050(10) C5 0.0255(13) 0.0178(11) 0.0205(12) -0.0014(9) -0.0032(10) -0.0008(9) C6 0.0475(19) 0.0487(19) 0.0337(16) 0.0055(14) -0.0015(14) -0.0232(15) C7 0.0355(15) 0.0351(15) 0.0235(13) -0.0099(11) -0.0026(11) -0.0088(12) C8 0.065(2) 0.0333(15) 0.0151(12) 0.0041(11) 0.0003(13) -0.0042(14) C9 0.036(2) 0.043(2) 0.0178(18) 0.0116(17) 0.0019(15) 0.0020(18) C10 0.062(3) 0.077(4) 0.023(2) 0.014(2) 0.011(2) 0.033(3) C11 0.0261(13) 0.0212(12) 0.0269(13) -0.0017(10) 0.0006(10) -0.0044(10) C12 0.0369(16) 0.0287(14) 0.0348(15) 0.0064(12) 0.0001(12) -0.0020(12) C13 0.0365(16) 0.0274(14) 0.0474(17) 0.0015(12) 0.0161(14) -0.0005(12) C14 0.0214(12) 0.0151(10) 0.0188(11) -0.0007(8) -0.0050(9) 0.0014(9) C15 0.0235(12) 0.0192(11) 0.0206(12) -0.0037(9) 0.0005(10) 0.0007(9) C16 0.0234(12) 0.0181(11) 0.0186(11) -0.0039(9) -0.0021(9) -0.0015(9) C17 0.0407(16) 0.0323(14) 0.0245(13) -0.0058(11) 0.0086(12) -0.0022(12) C18 0.0385(16) 0.0236(13) 0.0285(14) -0.0079(10) 0.0028(12) -0.0105(11) C19 0.0235(13) 0.0200(12) 0.0388(15) 0.0014(11) 0.0047(11) -0.0041(10) C20 0.048(2) 0.049(2) 0.073(3) 0.0351(19) -0.0080(18) -0.0174(16) C21 0.0310(17) 0.0335(17) 0.104(3) -0.0011(18) 0.0241(19) -0.0036(14) C22 0.0324(14) 0.0239(12) 0.0194(12) -0.0002(10) 0.0044(10) -0.0015(11) C23 0.0350(17) 0.0451(17) 0.0417(17) 0.0013(14) 0.0116(14) 0.0035(14) C24 0.0529(19) 0.0331(15) 0.0322(15) 0.0096(12) 0.0130(14) 0.0007(14) P 0.0427(4) 0.0170(3) 0.0197(3) -0.0009(2) 0.0051(3) 0.0011(3) F1 0.0840(17) 0.0699(15) 0.0664(15) 0.0062(12) 0.0464(13) -0.0023(13) F2 0.0851(15) 0.0376(10) 0.0334(10) 0.0032(8) -0.0212(10) 0.0051(10) F3 0.0416(11) 0.0738(14) 0.0459(11) -0.0056(10) 0.0120(9) -0.0051(10) F4 0.0527(12) 0.0321(9) 0.0510(11) 0.0095(8) -0.0109(9) 0.0098(8) F5 0.1145(18) 0.0227(9) 0.0371(10) -0.0090(7) 0.0065(11) -0.0105(10) F6 0.0647(12) 0.0209(8) 0.0394(9) -0.0060(7) -0.0131(9) -0.0013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.916(2) . ? Cu O 1.9297(18) 3_666 ? Cu O 1.9317(18) . ? Cu N2 1.950(2) . ? Cu Cu 3.0487(6) 3_666 ? O Cu 1.9297(18) 3_666 ? N1 C3 1.342(3) . ? N1 C1 1.465(3) . ? N2 C14 1.340(3) . ? N2 C2 1.471(3) . ? N3 C3 1.349(3) . ? N3 C4 1.398(3) . ? N3 C8 1.473(3) . ? N4 C3 1.361(3) . ? N4 C5 1.395(3) . ? N4 C11 1.470(3) . ? N5 C14 1.359(3) . ? N5 C15 1.400(3) . ? N5 C19 1.481(3) . ? N6 C14 1.359(3) . ? N6 C16 1.398(3) . ? N6 C22 1.475(3) . ? C1 C2 1.509(3) . ? C4 C5 1.345(4) . ? C4 C6 1.488(4) . ? C5 C7 1.495(3) . ? C8 C9' 1.393(10) . ? C8 C10 1.449(5) . ? C8 C9 1.545(5) . ? C8 C10' 1.589(9) . ? C11 C13 1.516(4) . ? C11 C12 1.519(4) . ? C15 C16 1.351(3) . ? C15 C17 1.492(3) . ? C16 C18 1.492(3) . ? C19 C21 1.496(4) . ? C19 C20 1.503(4) . ? C22 C24 1.515(4) . ? C22 C23 1.515(4) . ? P F1 1.574(2) . ? P F4 1.5749(18) . ? P F5 1.5898(18) . ? P F3 1.591(2) . ? P F6 1.5936(16) . ? P F2 1.6109(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu O 174.92(10) . 3_666 ? N1 Cu O 100.78(8) . . ? O Cu O 75.72(8) 3_666 . ? N1 Cu N2 84.52(8) . . ? O Cu N2 99.32(8) 3_666 . ? O Cu N2 172.48(9) . . ? N1 Cu Cu 138.50(6) . 3_666 ? O Cu Cu 37.88(5) 3_666 3_666 ? O Cu Cu 37.84(5) . 3_666 ? N2 Cu Cu 136.95(6) . 3_666 ? Cu O Cu 104.28(8) 3_666 . ? C3 N1 C1 119.12(19) . . ? C3 N1 Cu 128.70(16) . . ? C1 N1 Cu 110.87(15) . . ? C14 N2 C2 119.9(2) . . ? C14 N2 Cu 120.62(16) . . ? C2 N2 Cu 111.98(15) . . ? C3 N3 C4 109.6(2) . . ? C3 N3 C8 122.6(2) . . ? C4 N3 C8 127.4(2) . . ? C3 N4 C5 109.4(2) . . ? C3 N4 C11 121.7(2) . . ? C5 N4 C11 129.0(2) . . ? C14 N5 C15 109.35(19) . . ? C14 N5 C19 122.3(2) . . ? C15 N5 C19 127.3(2) . . ? C14 N6 C16 109.4(2) . . ? C14 N6 C22 121.19(19) . . ? C16 N6 C22 128.5(2) . . ? N1 C1 C2 106.8(2) . . ? N2 C2 C1 106.8(2) . . ? N1 C3 N3 125.4(2) . . ? N1 C3 N4 127.9(2) . . ? N3 C3 N4 106.6(2) . . ? C5 C4 N3 107.2(2) . . ? C5 C4 C6 128.9(2) . . ? N3 C4 C6 123.9(2) . . ? C4 C5 N4 107.2(2) . . ? C4 C5 C7 128.0(2) . . ? N4 C5 C7 124.7(2) . . ? C9' C8 C10 116.5(6) . . ? C9' C8 N3 124.0(6) . . ? C10 C8 N3 114.6(3) . . ? C9' C8 C9 28.7(6) . . ? C10 C8 C9 113.5(3) . . ? N3 C8 C9 108.0(3) . . ? C9' C8 C10' 117.3(7) . . ? C10 C8 C10' 50.8(5) . . ? N3 C8 C10' 111.8(4) . . ? C9 C8 C10' 140.0(5) . . ? N4 C11 C13 110.8(2) . . ? N4 C11 C12 112.1(2) . . ? C13 C11 C12 112.9(2) . . ? N2 C14 N5 129.8(2) . . ? N2 C14 N6 123.4(2) . . ? N5 C14 N6 106.75(19) . . ? C16 C15 N5 107.2(2) . . ? C16 C15 C17 127.7(2) . . ? N5 C15 C17 125.1(2) . . ? C15 C16 N6 107.3(2) . . ? C15 C16 C18 128.4(2) . . ? N6 C16 C18 124.3(2) . . ? N5 C19 C21 111.6(2) . . ? N5 C19 C20 112.4(2) . . ? C21 C19 C20 114.9(3) . . ? N6 C22 C24 113.0(2) . . ? N6 C22 C23 110.3(2) . . ? C24 C22 C23 113.0(2) . . ? F1 P F4 92.40(13) . . ? F1 P F5 89.80(12) . . ? F4 P F5 90.65(11) . . ? F1 P F3 177.48(13) . . ? F4 P F3 90.07(11) . . ? F5 P F3 89.64(12) . . ? F1 P F6 90.38(12) . . ? F4 P F6 89.85(10) . . ? F5 P F6 179.46(13) . . ? F3 P F6 90.16(11) . . ? F1 P F2 89.07(13) . . ? F4 P F2 178.49(12) . . ? F5 P F2 89.73(11) . . ? F3 P F2 88.47(12) . . ? F6 P F2 89.77(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 N1 Cu O Cu 176.23(11) . . . 3_666 ? O Cu O Cu 0.0 3_666 . . 3_666 ? N2 Cu O Cu -49.4(7) . . . 3_666 ? O Cu N1 C3 33.9(12) 3_666 . . . ? O Cu N1 C3 -12.1(3) . . . . ? N2 Cu N1 C3 173.3(3) . . . . ? Cu Cu N1 C3 -8.6(3) 3_666 . . . ? O Cu N1 C1 -159.5(10) 3_666 . . . ? O Cu N1 C1 154.50(18) . . . . ? N2 Cu N1 C1 -20.11(18) . . . . ? Cu Cu N1 C1 157.99(13) 3_666 . . . ? N1 Cu N2 C14 -156.5(2) . . . . ? O Cu N2 C14 20.2(2) 3_666 . . . ? O Cu N2 C14 68.3(7) . . . . ? Cu Cu N2 C14 25.3(3) 3_666 . . . ? N1 Cu N2 C2 -6.79(19) . . . . ? O Cu N2 C2 169.87(19) 3_666 . . . ? O Cu N2 C2 -141.9(6) . . . . ? Cu Cu N2 C2 175.06(15) 3_666 . . . ? C3 N1 C1 C2 -150.1(2) . . . . ? Cu N1 C1 C2 41.8(2) . . . . ? C14 N2 C2 C1 -179.3(2) . . . . ? Cu N2 C2 C1 30.8(3) . . . . ? N1 C1 C2 N2 -46.0(3) . . . . ? C1 N1 C3 N3 99.6(3) . . . . ? Cu N1 C3 N3 -94.8(3) . . . . ? C1 N1 C3 N4 -82.5(3) . . . . ? Cu N1 C3 N4 83.2(3) . . . . ? C4 N3 C3 N1 179.6(2) . . . . ? C8 N3 C3 N1 -7.4(4) . . . . ? C4 N3 C3 N4 1.3(3) . . . . ? C8 N3 C3 N4 174.3(2) . . . . ? C5 N4 C3 N1 179.8(2) . . . . ? C11 N4 C3 N1 0.8(4) . . . . ? C5 N4 C3 N3 -1.9(3) . . . . ? C11 N4 C3 N3 179.1(2) . . . . ? C3 N3 C4 C5 -0.2(3) . . . . ? C8 N3 C4 C5 -172.7(2) . . . . ? C3 N3 C4 C6 179.7(3) . . . . ? C8 N3 C4 C6 7.1(4) . . . . ? N3 C4 C5 N4 -1.0(3) . . . . ? C6 C4 C5 N4 179.2(3) . . . . ? N3 C4 C5 C7 176.0(2) . . . . ? C6 C4 C5 C7 -3.9(5) . . . . ? C3 N4 C5 C4 1.8(3) . . . . ? C11 N4 C5 C4 -179.3(2) . . . . ? C3 N4 C5 C7 -175.3(2) . . . . ? C11 N4 C5 C7 3.6(4) . . . . ? C3 N3 C8 C9' -73.7(8) . . . . ? C4 N3 C8 C9' 97.9(9) . . . . ? C3 N3 C8 C10 131.8(4) . . . . ? C4 N3 C8 C10 -56.5(4) . . . . ? C3 N3 C8 C9 -100.5(3) . . . . ? C4 N3 C8 C9 71.1(4) . . . . ? C3 N3 C8 C10' 76.3(6) . . . . ? C4 N3 C8 C10' -112.0(5) . . . . ? C3 N4 C11 C13 104.9(3) . . . . ? C5 N4 C11 C13 -73.9(3) . . . . ? C3 N4 C11 C12 -128.0(2) . . . . ? C5 N4 C11 C12 53.2(3) . . . . ? C2 N2 C14 N5 -55.7(4) . . . . ? Cu N2 C14 N5 91.7(3) . . . . ? C2 N2 C14 N6 128.3(3) . . . . ? Cu N2 C14 N6 -84.3(3) . . . . ? C15 N5 C14 N2 -177.3(2) . . . . ? C19 N5 C14 N2 -8.3(4) . . . . ? C15 N5 C14 N6 -0.7(3) . . . . ? C19 N5 C14 N6 168.3(2) . . . . ? C16 N6 C14 N2 177.1(2) . . . . ? C22 N6 C14 N2 -13.0(4) . . . . ? C16 N6 C14 N5 0.3(3) . . . . ? C22 N6 C14 N5 170.2(2) . . . . ? C14 N5 C15 C16 0.9(3) . . . . ? C19 N5 C15 C16 -167.4(2) . . . . ? C14 N5 C15 C17 -179.6(2) . . . . ? C19 N5 C15 C17 12.1(4) . . . . ? N5 C15 C16 N6 -0.6(3) . . . . ? C17 C15 C16 N6 179.8(2) . . . . ? N5 C15 C16 C18 177.1(2) . . . . ? C17 C15 C16 C18 -2.5(4) . . . . ? C14 N6 C16 C15 0.2(3) . . . . ? C22 N6 C16 C15 -168.7(2) . . . . ? C14 N6 C16 C18 -177.6(2) . . . . ? C22 N6 C16 C18 13.5(4) . . . . ? C14 N5 C19 C21 -111.1(3) . . . . ? C15 N5 C19 C21 55.9(4) . . . . ? C14 N5 C19 C20 118.2(3) . . . . ? C15 N5 C19 C20 -74.9(3) . . . . ? C14 N6 C22 C24 132.7(2) . . . . ? C16 N6 C22 C24 -59.6(3) . . . . ? C14 N6 C22 C23 -99.7(3) . . . . ? C16 N6 C22 C23 68.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.911 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.072 # Attachment 'DEIA.CIF' data_deia _database_code_depnum_ccdc_archive 'CCDC 663320' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H53 Cu F6 N7 P' _chemical_formula_weight 756.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0257(14) _cell_length_b 16.6650(18) _cell_length_c 17.4258(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.982(2) _cell_angle_gamma 90.00 _cell_volume 3754.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 7093 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 0.687 _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 133(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 1000 CCD' _diffrn_measurement_method '\w- and \f-scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32833 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.0933 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7680 _reflns_number_gt 5061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _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 'SIEMENS XP' _computing_publication_material SHELXL-97 _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^)+(0.0679P)^2^+0.4033P] 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 'methyls rigid and others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7680 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.008 _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 P P 0.70587(9) 0.63484(7) 0.79852(6) 0.0359(3) Uani 1 1 d . . . Cu Cu 0.24310(3) 0.42864(3) 0.61896(2) 0.01857(14) Uani 1 1 d . . . C1 C 0.3027(2) 0.5720(2) 0.53364(19) 0.0164(7) Uani 1 1 d . . . C2 C 0.2955(3) 0.6036(2) 0.4059(2) 0.0207(8) Uani 1 1 d . . . C3 C 0.3832(3) 0.6353(2) 0.4418(2) 0.0222(8) Uani 1 1 d . . . C4 C 0.1371(3) 0.5348(2) 0.4540(2) 0.0214(8) Uani 1 1 d . . . H4 H 0.1232 0.5168 0.5065 0.026 Uiso 1 1 calc R . . C5 C 0.0604(3) 0.6016(3) 0.4301(3) 0.0376(11) Uani 1 1 d . . . H5A H 0.0725 0.6465 0.4664 0.045 Uiso 1 1 calc R . . H5B H -0.0102 0.5815 0.4306 0.045 Uiso 1 1 calc R . . H5C H 0.0694 0.6199 0.3779 0.045 Uiso 1 1 calc R . . C6 C 0.1218(3) 0.4618(3) 0.4016(2) 0.0361(10) Uani 1 1 d . . . H6A H 0.1281 0.4777 0.3482 0.043 Uiso 1 1 calc R . . H6B H 0.0529 0.4391 0.4043 0.043 Uiso 1 1 calc R . . H6C H 0.1745 0.4214 0.4184 0.043 Uiso 1 1 calc R . . C7 C 0.2585(3) 0.6043(3) 0.3216(2) 0.0304(9) Uani 1 1 d . . . H7A H 0.3017 0.6406 0.2951 0.036 Uiso 1 1 calc R . . H7B H 0.1865 0.6226 0.3136 0.036 Uiso 1 1 calc R . . H7C H 0.2628 0.5500 0.3007 0.036 Uiso 1 1 calc R . . C8 C 0.4630(3) 0.6825(3) 0.4072(2) 0.0328(10) Uani 1 1 d . . . H8A H 0.5205 0.6472 0.3982 0.039 Uiso 1 1 calc R . . H8B H 0.4887 0.7256 0.4427 0.039 Uiso 1 1 calc R . . H8C H 0.4325 0.7058 0.3580 0.039 Uiso 1 1 calc R . . C9 C 0.4784(3) 0.6247(2) 0.5810(2) 0.0185(8) Uani 1 1 d . . . H9 H 0.4647 0.5903 0.6256 0.022 Uiso 1 1 calc R . . C10 C 0.5791(3) 0.5947(2) 0.5548(2) 0.0271(9) Uani 1 1 d . . . H10A H 0.5667 0.5435 0.5276 0.033 Uiso 1 1 calc R . . H10B H 0.6308 0.5872 0.6000 0.033 Uiso 1 1 calc R . . H10C H 0.6045 0.6342 0.5199 0.033 Uiso 1 1 calc R . . C11 C 0.4869(3) 0.7103(2) 0.6106(2) 0.0286(9) Uani 1 1 d . . . H11A H 0.5004 0.7463 0.5685 0.034 Uiso 1 1 calc R . . H11B H 0.5437 0.7141 0.6528 0.034 Uiso 1 1 calc R . . H11C H 0.4219 0.7258 0.6297 0.034 Uiso 1 1 calc R . . C12 C 0.2949(3) 0.5842(2) 0.6713(2) 0.0227(8) Uani 1 1 d . . . H12A H 0.2849 0.6425 0.6626 0.027 Uiso 1 1 calc R . . H12B H 0.3666 0.5749 0.6957 0.027 Uiso 1 1 calc R . . C13 C 0.2179(3) 0.5522(2) 0.7223(2) 0.0210(8) Uani 1 1 d . . . H13A H 0.2312 0.5757 0.7748 0.025 Uiso 1 1 calc R . . H13B H 0.1464 0.5658 0.7002 0.025 Uiso 1 1 calc R . . C14 C 0.2289(3) 0.4276(2) 0.7926(2) 0.0192(7) Uani 1 1 d . . . C15 C 0.2718(3) 0.3437(2) 0.8939(2) 0.0218(8) Uani 1 1 d . . . C16 C 0.1933(3) 0.3889(2) 0.91055(19) 0.0197(8) Uani 1 1 d . . . C17 C 0.3828(3) 0.3429(2) 0.7797(2) 0.0227(8) Uani 1 1 d . . . H17 H 0.3754 0.3720 0.7291 0.027 Uiso 1 1 calc R . . C18 C 0.3821(4) 0.2537(2) 0.7605(3) 0.0389(11) Uani 1 1 d . . . H18A H 0.4001 0.2228 0.8080 0.047 Uiso 1 1 calc R . . H18B H 0.4327 0.2429 0.7245 0.047 Uiso 1 1 calc R . . H18C H 0.3130 0.2381 0.7365 0.047 Uiso 1 1 calc R . . C19 C 0.4843(3) 0.3692(3) 0.8226(3) 0.0600(16) Uani 1 1 d . . . H19A H 0.4836 0.4274 0.8302 0.072 Uiso 1 1 calc R . . H19B H 0.5405 0.3549 0.7926 0.072 Uiso 1 1 calc R . . H19C H 0.4949 0.3423 0.8730 0.072 Uiso 1 1 calc R . . C20 C 0.3296(3) 0.2808(2) 0.9425(2) 0.0322(10) Uani 1 1 d . . . H20A H 0.2992 0.2747 0.9910 0.039 Uiso 1 1 calc R . . H20B H 0.4022 0.2967 0.9540 0.039 Uiso 1 1 calc R . . H20C H 0.3252 0.2297 0.9146 0.039 Uiso 1 1 calc R . . C21 C 0.1446(3) 0.3909(2) 0.9843(2) 0.0272(9) Uani 1 1 d . . . H21A H 0.1738 0.3479 1.0187 0.033 Uiso 1 1 calc R . . H21B H 0.0697 0.3831 0.9727 0.033 Uiso 1 1 calc R . . H21C H 0.1584 0.4429 1.0098 0.033 Uiso 1 1 calc R . . C22 C 0.0666(3) 0.4860(2) 0.8316(2) 0.0235(8) Uani 1 1 d . . . H22 H 0.0654 0.5087 0.7784 0.028 Uiso 1 1 calc R . . C23 C 0.0607(3) 0.5563(2) 0.8854(3) 0.0371(11) Uani 1 1 d . . . H23A H 0.0588 0.5367 0.9382 0.044 Uiso 1 1 calc R . . H23B H -0.0020 0.5874 0.8690 0.044 Uiso 1 1 calc R . . H23C H 0.1216 0.5906 0.8838 0.044 Uiso 1 1 calc R . . C24 C -0.0258(3) 0.4301(3) 0.8293(3) 0.0372(10) Uani 1 1 d . . . H24A H -0.0168 0.3850 0.7946 0.045 Uiso 1 1 calc R . . H24B H -0.0890 0.4595 0.8104 0.045 Uiso 1 1 calc R . . H24C H -0.0311 0.4098 0.8814 0.045 Uiso 1 1 calc R . . C25 C 0.2191(3) 0.3311(2) 0.5741(2) 0.0203(8) Uani 1 1 d . . . C26 C 0.1747(3) 0.1870(2) 0.5369(2) 0.0290(9) Uani 1 1 d . . . C27 C 0.1188(3) 0.1501(3) 0.5903(3) 0.0439(12) Uani 1 1 d . . . C28 C 0.0966(4) 0.0691(3) 0.5780(4) 0.072(2) Uani 1 1 d . . . H28 H 0.0591 0.0410 0.6130 0.086 Uiso 1 1 calc R . . C29 C 0.1278(5) 0.0297(3) 0.5167(5) 0.088(3) Uani 1 1 d . . . H29 H 0.1125 -0.0258 0.5101 0.105 Uiso 1 1 calc R . . C30 C 0.1808(4) 0.0681(3) 0.4639(4) 0.070(2) Uani 1 1 d . . . H30 H 0.2011 0.0389 0.4214 0.085 Uiso 1 1 calc R . . C31 C 0.2050(3) 0.1486(3) 0.4719(3) 0.0424(12) Uani 1 1 d . . . C32 C 0.2602(4) 0.1934(4) 0.4155(3) 0.0700(18) Uani 1 1 d . . . H32A H 0.2746 0.1573 0.3737 0.084 Uiso 1 1 calc R . . H32B H 0.3255 0.2145 0.4417 0.084 Uiso 1 1 calc R . . H32C H 0.2169 0.2380 0.3938 0.084 Uiso 1 1 calc R . . C33 C 0.0850(4) 0.1961(3) 0.6567(3) 0.0541(14) Uani 1 1 d . . . H33A H 0.1460 0.2172 0.6890 0.065 Uiso 1 1 calc R . . H33B H 0.0466 0.1605 0.6877 0.065 Uiso 1 1 calc R . . H33C H 0.0405 0.2407 0.6369 0.065 Uiso 1 1 calc R . . F1 F 0.6587(2) 0.62759(18) 0.87850(14) 0.0542(8) Uani 1 1 d . . . F2 F 0.6066(2) 0.58802(16) 0.75717(15) 0.0521(7) Uani 1 1 d . . . F3 F 0.7638(2) 0.55208(18) 0.81739(18) 0.0680(9) Uani 1 1 d . . . F4 F 0.8038(2) 0.68185(19) 0.83987(15) 0.0605(8) Uani 1 1 d . . . F5 F 0.6455(2) 0.71730(16) 0.78143(17) 0.0627(8) Uani 1 1 d . . . F6 F 0.7505(2) 0.6408(2) 0.71856(15) 0.0768(10) Uani 1 1 d . . . N1 N 0.2758(2) 0.54044(17) 0.59767(16) 0.0176(6) Uani 1 1 d . . . N2 N 0.2444(2) 0.56476(17) 0.46253(16) 0.0181(6) Uani 1 1 d . . . N3 N 0.3888(2) 0.61492(16) 0.52114(16) 0.0162(6) Uani 1 1 d . . . N4 N 0.2318(2) 0.46496(17) 0.72563(16) 0.0196(7) Uani 1 1 d . . . N5 N 0.2934(2) 0.36652(17) 0.81876(17) 0.0198(7) Uani 1 1 d . . . N6 N 0.1655(2) 0.44175(17) 0.84817(16) 0.0178(6) Uani 1 1 d . . . N7 N 0.2017(2) 0.26798(19) 0.54998(18) 0.0237(7) 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 P 0.0391(7) 0.0422(7) 0.0246(6) -0.0048(5) -0.0039(5) 0.0075(5) Cu 0.0232(2) 0.0149(2) 0.0184(2) -0.00220(19) 0.00542(17) -0.0009(2) C1 0.0158(17) 0.0117(16) 0.0217(18) -0.0036(15) 0.0025(14) 0.0041(15) C2 0.0208(19) 0.0238(19) 0.0172(18) 0.0035(16) 0.0010(15) -0.0003(16) C3 0.021(2) 0.026(2) 0.0200(19) 0.0064(16) 0.0064(16) 0.0003(16) C4 0.0120(18) 0.028(2) 0.024(2) 0.0028(16) 0.0018(15) -0.0012(15) C5 0.020(2) 0.040(2) 0.052(3) -0.002(2) 0.002(2) 0.0034(19) C6 0.032(2) 0.032(2) 0.044(3) -0.006(2) 0.000(2) -0.0109(19) C7 0.029(2) 0.042(2) 0.020(2) 0.0050(18) 0.0002(17) -0.0045(19) C8 0.024(2) 0.050(3) 0.025(2) 0.0100(19) 0.0048(17) -0.012(2) C9 0.0145(18) 0.0207(19) 0.0197(18) -0.0007(15) 0.0002(15) -0.0024(15) C10 0.019(2) 0.033(2) 0.028(2) -0.0041(17) -0.0019(16) 0.0028(17) C11 0.023(2) 0.033(2) 0.030(2) -0.0050(18) 0.0026(17) 0.0043(17) C12 0.033(2) 0.017(2) 0.0191(19) -0.0043(15) 0.0095(16) -0.0038(16) C13 0.031(2) 0.0151(19) 0.0180(19) -0.0026(14) 0.0068(16) 0.0034(15) C14 0.0195(18) 0.0172(17) 0.0201(18) -0.0049(16) -0.0004(14) -0.0055(16) C15 0.022(2) 0.025(2) 0.017(2) 0.0026(15) -0.0019(16) -0.0017(16) C16 0.0203(19) 0.026(2) 0.0130(18) 0.0021(15) 0.0026(15) -0.0038(16) C17 0.023(2) 0.022(2) 0.025(2) 0.0030(16) 0.0071(16) 0.0040(16) C18 0.046(3) 0.026(2) 0.049(3) -0.009(2) 0.023(2) -0.001(2) C19 0.029(3) 0.074(4) 0.080(4) -0.041(3) 0.016(3) -0.008(3) C20 0.038(2) 0.032(2) 0.026(2) 0.0059(18) -0.0009(19) 0.0045(19) C21 0.028(2) 0.035(2) 0.018(2) 0.0026(17) 0.0036(16) -0.0025(18) C22 0.0175(19) 0.031(2) 0.023(2) 0.0029(17) 0.0049(16) 0.0045(16) C23 0.031(2) 0.038(3) 0.044(3) -0.005(2) 0.012(2) 0.0074(19) C24 0.019(2) 0.041(3) 0.049(3) 0.009(2) -0.0050(19) -0.001(2) C25 0.023(2) 0.018(2) 0.020(2) 0.0025(16) 0.0073(16) 0.0002(16) C26 0.021(2) 0.0133(19) 0.050(3) -0.0012(18) -0.0079(19) -0.0009(16) C27 0.028(2) 0.032(3) 0.065(3) 0.019(2) -0.020(2) -0.004(2) C28 0.051(3) 0.039(3) 0.114(5) 0.035(4) -0.041(3) -0.026(3) C29 0.060(4) 0.019(3) 0.164(8) -0.003(4) -0.068(5) -0.002(3) C30 0.037(3) 0.041(3) 0.121(6) -0.043(4) -0.040(3) 0.016(3) C31 0.023(2) 0.030(2) 0.069(3) -0.026(2) -0.014(2) 0.0059(19) C32 0.037(3) 0.092(4) 0.085(4) -0.049(4) 0.026(3) -0.010(3) C33 0.042(3) 0.067(4) 0.052(3) 0.035(3) 0.002(2) -0.009(3) F1 0.0529(17) 0.079(2) 0.0304(14) -0.0021(13) 0.0037(13) 0.0051(15) F2 0.0512(17) 0.0557(18) 0.0458(16) -0.0108(13) -0.0087(13) -0.0013(14) F3 0.067(2) 0.060(2) 0.073(2) -0.0076(16) -0.0081(16) 0.0310(16) F4 0.0531(18) 0.081(2) 0.0426(16) 0.0076(15) -0.0146(13) -0.0167(16) F5 0.074(2) 0.0410(16) 0.0647(19) 0.0021(14) -0.0230(16) 0.0100(15) F6 0.062(2) 0.139(3) 0.0296(15) -0.0009(18) 0.0075(14) -0.005(2) N1 0.0256(17) 0.0145(14) 0.0131(15) -0.0004(12) 0.0043(13) -0.0020(13) N2 0.0183(15) 0.0189(16) 0.0175(15) 0.0016(13) 0.0033(12) 0.0001(13) N3 0.0125(15) 0.0200(16) 0.0158(15) 0.0015(12) 0.0014(12) 0.0011(12) N4 0.0292(18) 0.0164(15) 0.0145(15) 0.0007(12) 0.0083(13) 0.0052(13) N5 0.0212(16) 0.0188(16) 0.0198(16) 0.0013(13) 0.0036(13) 0.0032(13) N6 0.0149(15) 0.0236(17) 0.0147(15) -0.0001(12) 0.0014(12) 0.0007(12) N7 0.0209(17) 0.0227(18) 0.0277(18) -0.0033(14) 0.0032(14) 0.0013(14) _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 P F6 1.577(3) . ? P F3 1.587(3) . ? P F4 1.593(3) . ? P F5 1.593(3) . ? P F1 1.594(3) . ? P F2 1.604(3) . ? Cu C25 1.814(4) . ? Cu N1 1.957(3) . ? Cu N4 1.977(3) . ? C1 N1 1.319(4) . ? C1 N3 1.370(4) . ? C1 N2 1.377(4) . ? C2 C3 1.342(5) . ? C2 N2 1.412(4) . ? C2 C7 1.490(5) . ? C3 N3 1.417(4) . ? C3 C8 1.488(5) . ? C4 N2 1.475(4) . ? C4 C5 1.520(5) . ? C4 C6 1.521(5) . ? C9 N3 1.476(4) . ? C9 C11 1.516(5) . ? C9 C10 1.524(5) . ? C12 N1 1.470(4) . ? C12 C13 1.517(5) . ? C13 N4 1.465(4) . ? C14 N4 1.328(4) . ? C14 N5 1.362(4) . ? C14 N6 1.367(4) . ? C15 C16 1.329(5) . ? C15 N5 1.424(4) . ? C15 C20 1.493(5) . ? C16 N6 1.412(4) . ? C16 C21 1.502(5) . ? C17 N5 1.472(4) . ? C17 C19 1.502(6) . ? C17 C18 1.524(5) . ? C22 N6 1.481(4) . ? C22 C23 1.509(5) . ? C22 C24 1.518(5) . ? C25 N7 1.146(4) . ? C26 C27 1.392(6) . ? C26 C31 1.400(6) . ? C26 N7 1.406(5) . ? C27 C28 1.391(7) . ? C27 C33 1.499(7) . ? C28 C29 1.358(9) . ? C29 C30 1.374(10) . ? C30 C31 1.381(7) . ? C31 C32 1.488(7) . ? 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 F6 P F3 91.20(19) . . ? F6 P F4 90.45(17) . . ? F3 P F4 89.97(17) . . ? F6 P F5 90.39(18) . . ? F3 P F5 178.31(19) . . ? F4 P F5 90.57(16) . . ? F6 P F1 178.73(18) . . ? F3 P F1 88.67(17) . . ? F4 P F1 90.81(15) . . ? F5 P F1 89.73(16) . . ? F6 P F2 89.83(16) . . ? F3 P F2 90.41(16) . . ? F4 P F2 179.52(19) . . ? F5 P F2 89.05(15) . . ? F1 P F2 88.91(15) . . ? C25 Cu N1 143.28(14) . . ? C25 Cu N4 130.58(14) . . ? N1 Cu N4 85.96(12) . . ? N1 C1 N3 130.5(3) . . ? N1 C1 N2 123.5(3) . . ? N3 C1 N2 106.0(3) . . ? C3 C2 N2 107.6(3) . . ? C3 C2 C7 127.7(3) . . ? N2 C2 C7 124.6(3) . . ? C2 C3 N3 107.5(3) . . ? C2 C3 C8 128.1(3) . . ? N3 C3 C8 124.4(3) . . ? N2 C4 C5 111.3(3) . . ? N2 C4 C6 112.6(3) . . ? C5 C4 C6 112.8(3) . . ? N3 C9 C11 111.3(3) . . ? N3 C9 C10 112.8(3) . . ? C11 C9 C10 112.4(3) . . ? N1 C12 C13 106.5(3) . . ? N4 C13 C12 106.5(3) . . ? N4 C14 N5 124.2(3) . . ? N4 C14 N6 128.7(3) . . ? N5 C14 N6 107.1(3) . . ? C16 C15 N5 107.0(3) . . ? C16 C15 C20 128.4(3) . . ? N5 C15 C20 124.6(3) . . ? C15 C16 N6 108.5(3) . . ? C15 C16 C21 128.0(3) . . ? N6 C16 C21 123.3(3) . . ? N5 C17 C19 112.9(3) . . ? N5 C17 C18 112.2(3) . . ? C19 C17 C18 112.0(4) . . ? N6 C22 C23 112.0(3) . . ? N6 C22 C24 111.6(3) . . ? C23 C22 C24 113.1(3) . . ? N7 C25 Cu 175.7(3) . . ? C27 C26 C31 124.1(4) . . ? C27 C26 N7 117.2(4) . . ? C31 C26 N7 118.7(4) . . ? C28 C27 C26 116.3(5) . . ? C28 C27 C33 122.7(5) . . ? C26 C27 C33 121.1(4) . . ? C29 C28 C27 120.9(6) . . ? C28 C29 C30 121.6(5) . . ? C29 C30 C31 120.8(6) . . ? C30 C31 C26 116.2(5) . . ? C30 C31 C32 122.9(5) . . ? C26 C31 C32 120.8(4) . . ? C1 N1 C12 120.4(3) . . ? C1 N1 Cu 128.8(2) . . ? C12 N1 Cu 108.9(2) . . ? C1 N2 C2 109.5(3) . . ? C1 N2 C4 122.1(3) . . ? C2 N2 C4 127.3(3) . . ? C1 N3 C3 109.5(3) . . ? C1 N3 C9 122.5(3) . . ? C3 N3 C9 127.3(3) . . ? C14 N4 C13 118.9(3) . . ? C14 N4 Cu 134.1(2) . . ? C13 N4 Cu 106.8(2) . . ? C14 N5 C15 108.9(3) . . ? C14 N5 C17 122.4(3) . . ? C15 N5 C17 127.6(3) . . ? C14 N6 C16 108.4(3) . . ? C14 N6 C22 122.3(3) . . ? C16 N6 C22 126.6(3) . . ? C25 N7 C26 167.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N3 1.4(4) . . . . ? C7 C2 C3 N3 -175.9(4) . . . . ? N2 C2 C3 C8 -179.6(4) . . . . ? C7 C2 C3 C8 3.2(7) . . . . ? N1 C12 C13 N4 54.7(4) . . . . ? N5 C15 C16 N6 -1.3(4) . . . . ? C20 C15 C16 N6 178.2(3) . . . . ? N5 C15 C16 C21 -176.9(3) . . . . ? C20 C15 C16 C21 2.6(6) . . . . ? N1 Cu C25 N7 -166(5) . . . . ? N4 Cu C25 N7 7(5) . . . . ? C31 C26 C27 C28 2.5(6) . . . . ? N7 C26 C27 C28 -177.5(4) . . . . ? C31 C26 C27 C33 -177.3(4) . . . . ? N7 C26 C27 C33 2.7(6) . . . . ? C26 C27 C28 C29 -0.4(7) . . . . ? C33 C27 C28 C29 179.4(5) . . . . ? C27 C28 C29 C30 -1.0(8) . . . . ? C28 C29 C30 C31 0.5(8) . . . . ? C29 C30 C31 C26 1.4(7) . . . . ? C29 C30 C31 C32 -178.6(5) . . . . ? C27 C26 C31 C30 -3.0(6) . . . . ? N7 C26 C31 C30 177.0(4) . . . . ? C27 C26 C31 C32 177.0(4) . . . . ? N7 C26 C31 C32 -3.0(6) . . . . ? N3 C1 N1 C12 39.8(5) . . . . ? N2 C1 N1 C12 -141.9(3) . . . . ? N3 C1 N1 Cu -122.8(4) . . . . ? N2 C1 N1 Cu 55.5(4) . . . . ? C13 C12 N1 C1 156.0(3) . . . . ? C13 C12 N1 Cu -38.2(3) . . . . ? C25 Cu N1 C1 -9.5(4) . . . . ? N4 Cu N1 C1 175.5(3) . . . . ? C25 Cu N1 C12 -173.7(3) . . . . ? N4 Cu N1 C12 11.4(2) . . . . ? N1 C1 N2 C2 -178.6(3) . . . . ? N3 C1 N2 C2 0.0(4) . . . . ? N1 C1 N2 C4 12.4(5) . . . . ? N3 C1 N2 C4 -168.9(3) . . . . ? C3 C2 N2 C1 -0.9(4) . . . . ? C7 C2 N2 C1 176.5(4) . . . . ? C3 C2 N2 C4 167.3(3) . . . . ? C7 C2 N2 C4 -15.3(6) . . . . ? C5 C4 N2 C1 109.3(4) . . . . ? C6 C4 N2 C1 -122.8(4) . . . . ? C5 C4 N2 C2 -57.6(5) . . . . ? C6 C4 N2 C2 70.3(5) . . . . ? N1 C1 N3 C3 179.4(3) . . . . ? N2 C1 N3 C3 0.8(4) . . . . ? N1 C1 N3 C9 8.3(5) . . . . ? N2 C1 N3 C9 -170.2(3) . . . . ? C2 C3 N3 C1 -1.4(4) . . . . ? C8 C3 N3 C1 179.5(3) . . . . ? C2 C3 N3 C9 169.1(3) . . . . ? C8 C3 N3 C9 -10.0(6) . . . . ? C11 C9 N3 C1 -110.0(4) . . . . ? C10 C9 N3 C1 122.6(3) . . . . ? C11 C9 N3 C3 80.7(4) . . . . ? C10 C9 N3 C3 -46.7(5) . . . . ? N5 C14 N4 C13 -139.5(3) . . . . ? N6 C14 N4 C13 39.3(5) . . . . ? N5 C14 N4 Cu 45.1(5) . . . . ? N6 C14 N4 Cu -136.0(3) . . . . ? C12 C13 N4 C14 139.2(3) . . . . ? C12 C13 N4 Cu -44.3(3) . . . . ? C25 Cu N4 C14 18.6(4) . . . . ? N1 Cu N4 C14 -165.3(4) . . . . ? C25 Cu N4 C13 -157.1(2) . . . . ? N1 Cu N4 C13 19.0(2) . . . . ? N4 C14 N5 C15 177.1(3) . . . . ? N6 C14 N5 C15 -1.9(4) . . . . ? N4 C14 N5 C17 8.5(5) . . . . ? N6 C14 N5 C17 -170.5(3) . . . . ? C16 C15 N5 C14 2.0(4) . . . . ? C20 C15 N5 C14 -177.5(3) . . . . ? C16 C15 N5 C17 169.9(3) . . . . ? C20 C15 N5 C17 -9.6(6) . . . . ? C19 C17 N5 C14 105.7(4) . . . . ? C18 C17 N5 C14 -126.5(4) . . . . ? C19 C17 N5 C15 -60.7(5) . . . . ? C18 C17 N5 C15 67.1(5) . . . . ? N4 C14 N6 C16 -177.9(3) . . . . ? N5 C14 N6 C16 1.1(4) . . . . ? N4 C14 N6 C22 19.6(5) . . . . ? N5 C14 N6 C22 -161.4(3) . . . . ? C15 C16 N6 C14 0.2(4) . . . . ? C21 C16 N6 C14 176.0(3) . . . . ? C15 C16 N6 C22 161.7(3) . . . . ? C21 C16 N6 C22 -22.5(5) . . . . ? C23 C22 N6 C14 -125.5(4) . . . . ? C24 C22 N6 C14 106.6(4) . . . . ? C23 C22 N6 C16 75.3(4) . . . . ? C24 C22 N6 C16 -52.6(5) . . . . ? Cu C25 N7 C26 -6(6) . . . . ? C27 C26 N7 C25 15.9(18) . . . . ? C31 C26 N7 C25 -164.1(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.515 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.089