Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Chen, Wanzhi' _publ_contact_author_email chenwzz@zju.edu.cn _publ_section_title ; Facile Synthesis of Metal N-Heterocyclic Carbene Complexes ; loop_ _publ_author_name 'Wanzhi Chen' 'Bin Liu' 'Yin Zhang' 'Daichao Xu' # Attachment '- cifs.cif' data_080313e _database_code_depnum_ccdc_archive 'CCDC 782455' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cu F12 N8 O2 P2' _chemical_formula_weight 705.85 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8197(6) _cell_length_b 8.5461(10) _cell_length_c 11.1542(13) _cell_angle_alpha 101.646(2) _cell_angle_beta 106.212(2) _cell_angle_gamma 98.9490(10) _cell_volume 595.66(11) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 351 _exptl_absorpt_coefficient_mu 1.181 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6691 _exptl_absorpt_correction_T_max 0.7812 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 3078 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2059 _reflns_number_gt 1732 _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^)+(0.0689P)^2^+0.3710P] 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 2059 _refine_ls_number_parameters 243 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.064 _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 F6' F 0.797(4) 0.658(3) 0.3544(19) 0.083(5) Uani 0.50 1 d PD A 2 F1 F 0.847(3) 0.704(3) 0.3865(19) 0.091(6) Uani 0.50 1 d PD A 1 Cu1 Cu 1.0000 0.5000 0.5000 0.0355(2) Uani 1 2 d S . . P1 P 0.81255(15) 0.77399(11) 0.26229(9) 0.0406(3) Uani 1 1 d D . . F2 F 0.775(3) 0.843(2) 0.1382(12) 0.076(4) Uani 0.50 1 d PD A 1 F3 F 1.0399(17) 0.762(2) 0.2732(18) 0.099(6) Uani 0.50 1 d PD A 1 F4 F 0.738(2) 0.5972(10) 0.1733(13) 0.107(5) Uani 0.50 1 d PD A 1 F5 F 0.5798(16) 0.7827(15) 0.2464(16) 0.100(5) Uani 0.50 1 d PD A 1 F6 F 0.9013(13) 0.9563(10) 0.3467(9) 0.071(2) Uani 0.50 1 d PD A 1 F1' F 1.024(2) 0.732(2) 0.2450(16) 0.089(5) Uani 0.50 1 d PD A 2 F2' F 0.5968(17) 0.8029(17) 0.2751(13) 0.088(5) Uani 0.50 1 d PD A 2 F3' F 0.692(2) 0.6147(15) 0.1496(12) 0.112(5) Uani 0.50 1 d PD A 2 F4' F 0.833(3) 0.882(2) 0.1672(15) 0.098(6) Uani 0.50 1 d PD A 2 F5' F 0.911(3) 0.9183(16) 0.3763(13) 0.194(9) Uani 0.50 1 d PD A 2 N1 N 0.8034(4) 0.2689(3) 0.2074(3) 0.0366(6) Uani 1 1 d . . . N2 N 1.0717(5) 0.3505(4) 0.1492(3) 0.0417(7) Uani 1 1 d . . . N3 N 0.7396(4) 0.3148(3) 0.4071(3) 0.0358(6) Uani 1 1 d . . . N4 N 0.4964(5) 0.1287(4) 0.2167(3) 0.0449(7) Uani 1 1 d . . . O1 O 1.1141(4) 0.4303(3) 0.3664(2) 0.0410(6) Uani 1 1 d . . . C1 C 1.0057(5) 0.3563(4) 0.2511(3) 0.0358(7) Uani 1 1 d . . . C2 C 0.7444(7) 0.2078(5) 0.0720(3) 0.0498(10) Uani 1 1 d . . . H2 H 0.6149 0.1442 0.0171 0.060 Uiso 1 1 calc R . . C3 C 0.9103(7) 0.2590(5) 0.0389(4) 0.0520(10) Uani 1 1 d . . . H3 H 0.9175 0.2372 -0.0447 0.062 Uiso 1 1 calc R . . C4 C 0.6740(5) 0.2358(4) 0.2819(3) 0.0354(7) Uani 1 1 d . . . C5 C 0.3717(6) 0.0905(5) 0.2841(4) 0.0497(9) Uani 1 1 d . . . H5 H 0.2434 0.0167 0.2412 0.060 Uiso 1 1 calc R . . C6 C 0.4255(6) 0.1566(5) 0.4155(4) 0.0503(10) Uani 1 1 d . . . H6 H 0.3397 0.1257 0.4625 0.060 Uiso 1 1 calc R . . C7 C 0.6098(6) 0.2686(5) 0.4727(4) 0.0459(9) Uani 1 1 d . . . H7 H 0.6493 0.3161 0.5610 0.055 Uiso 1 1 calc R . . C8 C 1.2736(6) 0.4414(5) 0.1539(4) 0.0527(10) Uani 1 1 d . . . H8A H 1.2618 0.5486 0.1431 0.079 Uiso 1 1 calc R . . H8B H 1.3167 0.3841 0.0859 0.079 Uiso 1 1 calc R . . H8C H 1.3756 0.4517 0.2359 0.079 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 F6' 0.079(6) 0.110(9) 0.093(11) 0.070(9) 0.043(7) 0.028(5) F1 0.125(15) 0.139(14) 0.072(8) 0.075(10) 0.061(9) 0.094(13) Cu1 0.0289(3) 0.0457(4) 0.0277(3) 0.0069(2) 0.0063(2) 0.0055(2) P1 0.0411(6) 0.0438(5) 0.0424(6) 0.0161(4) 0.0169(4) 0.0121(4) F2 0.088(9) 0.117(10) 0.043(3) 0.038(4) 0.023(4) 0.049(7) F3 0.027(4) 0.116(9) 0.176(14) 0.089(9) 0.030(5) 0.017(4) F4 0.115(9) 0.036(4) 0.135(10) -0.018(4) 0.001(6) 0.036(5) F5 0.040(5) 0.067(5) 0.180(12) 0.054(6) 0.006(5) -0.002(4) F6 0.073(4) 0.043(3) 0.076(6) 0.003(3) 0.002(3) 0.012(3) F1' 0.093(10) 0.140(11) 0.091(6) 0.064(6) 0.069(6) 0.076(8) F2' 0.099(9) 0.117(9) 0.123(7) 0.070(6) 0.093(7) 0.083(7) F3' 0.075(6) 0.159(11) 0.063(5) -0.016(6) 0.027(5) -0.032(6) F4' 0.113(13) 0.103(9) 0.143(14) 0.095(11) 0.079(11) 0.058(9) F5' 0.33(2) 0.111(10) 0.072(7) -0.017(7) 0.054(9) -0.070(11) N1 0.0389(16) 0.0385(15) 0.0286(14) 0.0063(12) 0.0092(12) 0.0040(12) N2 0.0466(18) 0.0457(17) 0.0327(15) 0.0075(13) 0.0157(13) 0.0081(14) N3 0.0362(16) 0.0404(15) 0.0300(14) 0.0097(12) 0.0090(12) 0.0087(12) N4 0.0448(18) 0.0403(16) 0.0403(17) 0.0046(13) 0.0095(14) -0.0013(14) O1 0.0286(12) 0.0568(15) 0.0321(13) 0.0066(11) 0.0066(10) 0.0064(11) C1 0.0382(19) 0.0355(17) 0.0338(18) 0.0082(14) 0.0109(15) 0.0110(15) C2 0.060(3) 0.047(2) 0.0290(18) 0.0002(16) 0.0089(17) -0.0028(18) C3 0.067(3) 0.050(2) 0.0319(19) 0.0026(16) 0.0184(18) 0.0011(19) C4 0.0346(18) 0.0342(17) 0.0381(18) 0.0132(14) 0.0099(14) 0.0083(14) C5 0.043(2) 0.045(2) 0.054(2) 0.0077(18) 0.0137(18) -0.0017(17) C6 0.047(2) 0.051(2) 0.057(2) 0.0161(18) 0.0238(19) 0.0038(18) C7 0.046(2) 0.054(2) 0.037(2) 0.0112(17) 0.0161(17) 0.0055(18) C8 0.048(2) 0.065(3) 0.052(2) 0.019(2) 0.0262(19) 0.012(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 F6' P1 1.581(14) . ? F1 P1 1.592(13) . ? Cu1 O1 1.901(2) 2_766 ? Cu1 O1 1.901(2) . ? Cu1 N3 2.042(3) 2_766 ? Cu1 N3 2.042(3) . ? P1 F5' 1.490(12) . ? P1 F3 1.543(10) . ? P1 F4 1.549(8) . ? P1 F4' 1.562(13) . ? P1 F5 1.562(10) . ? P1 F2' 1.569(8) . ? P1 F6 1.574(8) . ? P1 F3' 1.579(11) . ? P1 F2 1.583(12) . ? P1 F1' 1.590(11) . ? N1 C1 1.363(4) . ? N1 C4 1.406(4) . ? N1 C2 1.411(4) . ? N2 C1 1.329(4) . ? N2 C3 1.387(5) . ? N2 C8 1.453(5) . ? N3 C4 1.335(4) . ? N3 C7 1.358(4) . ? N4 C4 1.315(4) . ? N4 C5 1.329(5) . ? O1 C1 1.263(4) . ? C2 C3 1.324(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C5 C6 1.380(6) . ? C5 H5 0.9300 . ? C6 C7 1.354(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.000(1) 2_766 . ? O1 Cu1 N3 89.73(10) 2_766 2_766 ? O1 Cu1 N3 90.27(10) . 2_766 ? O1 Cu1 N3 90.27(11) 2_766 . ? O1 Cu1 N3 89.73(10) . . ? N3 Cu1 N3 180.00(14) 2_766 . ? F5' P1 F3 85.0(11) . . ? F5' P1 F4 163.1(8) . . ? F3 P1 F4 88.3(9) . . ? F5' P1 F4' 91.5(10) . . ? F3 P1 F4' 85.8(11) . . ? F4 P1 F4' 103.4(9) . . ? F5' P1 F5 96.9(10) . . ? F3 P1 F5 178.0(9) . . ? F4 P1 F5 90.1(7) . . ? F4' P1 F5 93.6(10) . . ? F5' P1 F2' 86.3(10) . . ? F3 P1 F2' 170.6(9) . . ? F4 P1 F2' 99.2(7) . . ? F4' P1 F2' 97.9(10) . . ? F5 P1 F2' 11.4(10) . . ? F5' P1 F6 18.8(8) . . ? F3 P1 F6 88.2(8) . . ? F4 P1 F6 175.3(7) . . ? F4' P1 F6 73.3(8) . . ? F5 P1 F6 93.4(6) . . ? F2' P1 F6 84.6(6) . . ? F5' P1 F3' 173.8(8) . . ? F3 P1 F3' 99.2(8) . . ? F4 P1 F3' 15.3(9) . . ? F4' P1 F3' 93.4(8) . . ? F5 P1 F3' 79.0(7) . . ? F2' P1 F3' 89.3(7) . . ? F6 P1 F3' 164.3(7) . . ? F5' P1 F6' 90.6(10) . . ? F3 P1 F6' 92.1(11) . . ? F4 P1 F6' 74.3(10) . . ? F4' P1 F6' 176.9(13) . . ? F5 P1 F6' 88.5(11) . . ? F2' P1 F6' 84.6(10) . . ? F6 P1 F6' 108.9(9) . . ? F3' P1 F6' 84.8(10) . . ? F5' P1 F2 106.6(9) . . ? F3 P1 F2 95.0(11) . . ? F4 P1 F2 89.3(9) . . ? F4' P1 F2 17.1(12) . . ? F5 P1 F2 83.9(10) . . ? F2' P1 F2 90.8(10) . . ? F6 P1 F2 87.9(8) . . ? F3' P1 F2 77.7(8) . . ? F6' P1 F2 161.9(10) . . ? F5' P1 F1' 97.1(11) . . ? F3 P1 F1' 12.2(12) . . ? F4 P1 F1' 77.1(9) . . ? F4' P1 F1' 83.7(11) . . ? F5 P1 F1' 165.8(9) . . ? F2' P1 F1' 176.3(9) . . ? F6 P1 F1' 99.1(8) . . ? F3' P1 F1' 87.3(8) . . ? F6' P1 F1' 93.7(12) . . ? F2 P1 F1' 89.9(11) . . ? F5' P1 F1 73.8(10) . . ? F3 P1 F1 85.7(10) . . ? F4 P1 F1 90.3(10) . . ? F4' P1 F1 163.6(11) . . ? F5 P1 F1 95.4(10) . . ? F2' P1 F1 88.6(9) . . ? F6 P1 F1 92.5(9) . . ? F3' P1 F1 101.8(10) . . ? F6' P1 F1 17.5(15) . . ? F2 P1 F1 179.2(10) . . ? F1' P1 F1 90.7(10) . . ? C1 N1 C4 127.2(3) . . ? C1 N1 C2 108.4(3) . . ? C4 N1 C2 124.3(3) . . ? C1 N2 C3 109.0(3) . . ? C1 N2 C8 124.2(3) . . ? C3 N2 C8 126.4(3) . . ? C4 N3 C7 114.2(3) . . ? C4 N3 Cu1 126.1(2) . . ? C7 N3 Cu1 119.6(2) . . ? C4 N4 C5 116.2(3) . . ? C1 O1 Cu1 124.3(2) . . ? O1 C1 N2 125.2(3) . . ? O1 C1 N1 127.4(3) . . ? N2 C1 N1 107.4(3) . . ? C3 C2 N1 106.3(3) . . ? C3 C2 H2 126.9 . . ? N1 C2 H2 126.9 . . ? C2 C3 N2 108.9(3) . . ? C2 C3 H3 125.5 . . ? N2 C3 H3 125.5 . . ? N4 C4 N3 127.4(3) . . ? N4 C4 N1 114.2(3) . . ? N3 C4 N1 118.4(3) . . ? N4 C5 C6 122.4(4) . . ? N4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C5 116.6(4) . . ? C7 C6 H6 121.7 . . ? C5 C6 H6 121.7 . . ? C6 C7 N3 123.1(3) . . ? C6 C7 H7 118.4 . . ? N3 C7 H7 118.4 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N3 C4 158.9(3) 2_766 . . . ? O1 Cu1 N3 C4 -21.1(3) . . . . ? N3 Cu1 N3 C4 24(100) 2_766 . . . ? O1 Cu1 N3 C7 -17.4(3) 2_766 . . . ? O1 Cu1 N3 C7 162.6(3) . . . . ? N3 Cu1 N3 C7 -153(100) 2_766 . . . ? O1 Cu1 O1 C1 41(100) 2_766 . . . ? N3 Cu1 O1 C1 -152.4(3) 2_766 . . . ? N3 Cu1 O1 C1 27.6(3) . . . . ? Cu1 O1 C1 N2 158.1(3) . . . . ? Cu1 O1 C1 N1 -21.9(5) . . . . ? C3 N2 C1 O1 -179.8(3) . . . . ? C8 N2 C1 O1 -5.9(6) . . . . ? C3 N2 C1 N1 0.2(4) . . . . ? C8 N2 C1 N1 174.1(3) . . . . ? C4 N1 C1 O1 -3.1(6) . . . . ? C2 N1 C1 O1 179.8(3) . . . . ? C4 N1 C1 N2 176.9(3) . . . . ? C2 N1 C1 N2 -0.2(4) . . . . ? C1 N1 C2 C3 0.2(4) . . . . ? C4 N1 C2 C3 -177.1(3) . . . . ? N1 C2 C3 N2 0.0(5) . . . . ? C1 N2 C3 C2 -0.1(5) . . . . ? C8 N2 C3 C2 -173.9(4) . . . . ? C5 N4 C4 N3 -2.6(5) . . . . ? C5 N4 C4 N1 178.3(3) . . . . ? C7 N3 C4 N4 4.3(5) . . . . ? Cu1 N3 C4 N4 -172.2(3) . . . . ? C7 N3 C4 N1 -176.6(3) . . . . ? Cu1 N3 C4 N1 6.8(4) . . . . ? C1 N1 C4 N4 -170.5(3) . . . . ? C2 N1 C4 N4 6.2(5) . . . . ? C1 N1 C4 N3 10.3(5) . . . . ? C2 N1 C4 N3 -173.0(3) . . . . ? C4 N4 C5 C6 -1.1(6) . . . . ? N4 C5 C6 C7 2.6(6) . . . . ? C5 C6 C7 N3 -0.7(6) . . . . ? C4 N3 C7 C6 -2.4(5) . . . . ? Cu1 N3 C7 C6 174.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.541 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.085 #===END data_091020h _database_code_depnum_ccdc_archive 'CCDC 782456' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cu F6 N8 P' _chemical_formula_weight 528.88 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 25.351(2) _cell_length_b 6.8638(7) _cell_length_c 11.9093(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.551(2) _cell_angle_gamma 90.00 _cell_volume 1996.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5790 _exptl_absorpt_correction_T_max 0.7878 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 5070 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1925 _reflns_number_gt 1483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SMART' _computing_publication_material 'Bruker SMART' _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^)+(0.1101P)^2^+8.0325P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1925 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1791 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.27968(3) 0.5000 0.48046(7) 0.0465(4) Uani 1 2 d S . . F1 F 0.0071(5) 0.236(3) 0.6921(13) 0.169(5) Uani 0.50 1 d P . . F2 F 0.0760(3) 0.3781(18) 0.8170(8) 0.112(3) Uani 0.50 1 d P . . F3 F -0.0055(4) 0.400(2) 0.8451(8) 0.138(6) Uani 0.50 1 d P . . F4 F -0.0387(3) 0.5000 0.6687(7) 0.156(4) Uani 1 2 d S . . F5 F 0.0451(3) 0.5000 0.6442(7) 0.154(4) Uani 1 2 d S . . F6 F 0.0322(6) 0.654(3) 0.7962(13) 0.151(5) Uani 0.50 1 d P . . N1 N 0.2732(2) 0.5000 0.7270(4) 0.0363(12) Uani 1 2 d S . . N2 N 0.1955(2) 0.5000 0.6067(5) 0.0538(17) Uani 1 2 d S . . N3 N 0.3626(3) 0.5000 0.7089(6) 0.070(2) Uani 1 2 d S . . N4 N 0.3439(3) 0.4322(12) 0.8929(6) 0.048(2) Uani 0.50 1 d P . . N5 N 0.2880(2) 0.5000 0.2374(4) 0.0407(13) Uani 1 2 d S . . N6 N 0.3659(3) 0.5000 0.3568(6) 0.074(2) Uani 1 2 d S . . N7 N 0.1991(2) 0.5000 0.2572(5) 0.0563(18) Uani 1 2 d S . . N8 N 0.2168(3) 0.5000 0.0715(6) 0.078(3) Uani 1 2 d S . . P1 P 0.01770(13) 0.4368(6) 0.7397(3) 0.0611(14) Uani 0.50 1 d P . . C1 C 0.2484(3) 0.5000 0.6101(5) 0.0390(15) Uani 1 2 d S . . C2 C 0.1869(3) 0.5000 0.7159(6) 0.0494(18) Uani 1 2 d S . . H2 H 0.1531 0.5000 0.7327 0.059 Uiso 1 2 calc SR . . C3 C 0.2347(3) 0.5000 0.7916(6) 0.0436(16) Uani 1 2 d S . . H3 H 0.2417 0.5000 0.8724 0.052 Uiso 1 2 calc SR . . C4 C 0.3298(3) 0.5000 0.7782(6) 0.065(2) Uani 1 2 d S . . C5 C 0.3971(4) 0.4029(19) 0.9410(9) 0.060(3) Uani 0.50 1 d P . . H5 H 0.4090 0.3851 1.0212 0.072 Uiso 0.50 1 d PR . . C6 C 0.4346(4) 0.398(2) 0.8787(9) 0.061(3) Uani 0.50 1 d P . . H6 H 0.4714 0.3727 0.9140 0.073 Uiso 0.50 1 d PR . . C7 C 0.4158(4) 0.4304(17) 0.7608(9) 0.060(4) Uani 0.50 1 d P . . H7 H 0.4391 0.4059 0.7137 0.072 Uiso 0.50 1 d PR . . C8 C 0.1518(3) 0.5000 0.4973(8) 0.102(5) Uani 1 2 d S . . H8A H 0.1200 0.4363 0.5092 0.154 Uiso 0.50 1 calc PR . . H8B H 0.1640 0.4318 0.4385 0.154 Uiso 0.50 1 calc PR . . H8C H 0.1428 0.6318 0.4726 0.154 Uiso 0.50 1 calc PR . . C9 C 0.3127(3) 0.5000 0.3535(6) 0.0494(18) Uani 1 2 d S . . C10 C 0.3743(3) 0.5000 0.2466(7) 0.070(3) Uani 1 2 d S . . H10 H 0.4080 0.5000 0.2295 0.084 Uiso 1 2 calc SR . . C11 C 0.3262(3) 0.5000 0.1709(6) 0.053(2) Uani 1 2 d S . . H11 H 0.3188 0.5000 0.0901 0.064 Uiso 1 2 calc SR . . C12 C 0.2310(3) 0.5000 0.1854(6) 0.0501(18) Uani 1 2 d S . . C13 C 0.1630(4) 0.4248(17) 0.0245(8) 0.057(3) Uani 0.50 1 d P . . H13 H 0.1533 0.3755 -0.0510 0.068 Uiso 0.50 1 d PR . . C14 C 0.1259(4) 0.4235(17) 0.0865(9) 0.055(3) Uani 0.50 1 d P . . H14 H 0.0888 0.4074 0.0511 0.066 Uiso 0.50 1 d PR . . C15 C 0.1458(4) 0.4474(17) 0.2063(8) 0.055(5) Uani 0.50 1 d P . . H15 H 0.1224 0.4271 0.2534 0.066 Uiso 0.50 1 d PR . . C16 C 0.4105(4) 0.4366(17) 0.4624(8) 0.057(4) Uani 0.50 1 d P . . H16A H 0.3969 0.4408 0.5302 0.086 Uiso 0.50 1 d PR . . H16B H 0.4413 0.5228 0.4731 0.086 Uiso 0.50 1 d PR . . H16C H 0.4217 0.3061 0.4510 0.086 Uiso 0.50 1 d PR . . 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 0.0401(6) 0.0722(8) 0.0331(5) 0.000 0.0199(4) 0.000 F1 0.118(9) 0.216(16) 0.154(11) -0.045(12) 0.005(8) -0.017(10) F2 0.057(4) 0.183(10) 0.093(6) 0.004(6) 0.012(4) 0.015(6) F3 0.100(6) 0.228(17) 0.105(6) 0.008(7) 0.063(6) -0.007(7) F4 0.063(4) 0.262(12) 0.126(6) 0.000 -0.005(4) 0.000 F5 0.107(5) 0.268(13) 0.099(5) 0.000 0.050(4) 0.000 F6 0.094(9) 0.212(16) 0.140(12) 0.006(11) 0.020(9) 0.001(10) N1 0.035(3) 0.051(3) 0.028(3) 0.000 0.017(2) 0.000 N2 0.033(3) 0.095(5) 0.037(3) 0.000 0.015(2) 0.000 N3 0.040(3) 0.129(7) 0.042(3) 0.000 0.014(3) 0.000 N4 0.043(4) 0.065(7) 0.037(4) -0.001(3) 0.012(3) 0.007(3) N5 0.037(3) 0.061(4) 0.030(3) 0.000 0.020(2) 0.000 N6 0.041(3) 0.148(8) 0.040(3) 0.000 0.023(3) 0.000 N7 0.041(3) 0.094(5) 0.039(3) 0.000 0.020(3) 0.000 N8 0.052(4) 0.146(8) 0.037(3) 0.000 0.017(3) 0.000 P1 0.0323(14) 0.102(4) 0.0487(15) 0.0016(16) 0.0107(11) -0.0029(14) C1 0.034(3) 0.053(4) 0.034(3) 0.000 0.016(3) 0.000 C2 0.039(4) 0.076(5) 0.040(4) 0.000 0.022(3) 0.000 C3 0.049(4) 0.057(4) 0.035(3) 0.000 0.028(3) 0.000 C4 0.047(4) 0.116(8) 0.036(4) 0.000 0.017(3) 0.000 C5 0.056(6) 0.080(8) 0.041(5) 0.003(5) 0.006(5) 0.008(6) C6 0.042(5) 0.084(8) 0.051(6) -0.001(6) 0.002(4) 0.009(5) C7 0.047(5) 0.087(11) 0.048(5) -0.005(5) 0.015(4) -0.002(5) C8 0.037(4) 0.222(15) 0.049(5) 0.000 0.014(4) 0.000 C9 0.034(3) 0.082(6) 0.035(4) 0.000 0.015(3) 0.000 C10 0.046(4) 0.129(9) 0.044(4) 0.000 0.025(4) 0.000 C11 0.046(4) 0.085(6) 0.037(4) 0.000 0.027(3) 0.000 C12 0.043(4) 0.078(5) 0.035(4) 0.000 0.019(3) 0.000 C13 0.054(5) 0.082(9) 0.034(4) -0.005(4) 0.010(4) 0.012(5) C14 0.048(5) 0.069(8) 0.047(5) -0.004(5) 0.012(4) 0.004(5) C15 0.045(5) 0.079(14) 0.044(5) -0.003(5) 0.018(4) -0.005(5) C16 0.035(4) 0.089(12) 0.047(5) 0.003(5) 0.011(4) 0.002(5) _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 C9 1.914(7) . ? Cu1 C1 1.916(6) . ? F1 F6 1.445(18) 6_565 ? F1 P1 1.484(18) . ? F2 F6 1.095(14) 6_565 ? F2 P1 1.571(9) . ? F2 F2 1.67(2) 6_565 ? F2 P1 1.980(10) 6_565 ? F3 F6 1.298(15) 6_565 ? F3 F3 1.38(3) 6_565 ? F3 P1 1.544(9) . ? F3 P1 1.892(12) 6_565 ? F4 P1 1.516(7) 6_565 ? F4 P1 1.516(7) . ? F5 P1 1.545(8) . ? F5 P1 1.545(8) 6_565 ? F6 P1 0.918(16) 6_565 ? F6 F2 1.094(14) 6_565 ? F6 F3 1.298(15) 6_565 ? F6 F1 1.445(17) 6_565 ? F6 P1 1.635(18) . ? N1 C1 1.366(8) . ? N1 C3 1.397(7) . ? N1 C4 1.401(9) . ? N2 C1 1.330(8) . ? N2 C2 1.376(9) . ? N2 C8 1.466(10) . ? N3 C4 1.319(9) . ? N3 C7 1.409(12) 6_565 ? N3 C7 1.409(12) . ? N4 N4 0.930(17) 6_565 ? N4 C5 1.331(12) . ? N4 C4 1.396(10) . ? N4 C5 1.735(14) 6_565 ? N5 C9 1.356(8) . ? N5 C11 1.405(8) . ? N5 C12 1.412(9) . ? N6 C9 1.340(9) . ? N6 C10 1.385(9) . ? N6 C16 1.512(11) 6_565 ? N6 C16 1.512(11) . ? N7 C12 1.325(9) . ? N7 C15 1.372(11) . ? N7 C15 1.372(11) 6_565 ? N8 C12 1.307(9) . ? N8 C13 1.426(12) . ? N8 C13 1.426(12) 6_565 ? P1 P1 0.868(8) 6_565 ? P1 F6 0.918(16) 6_565 ? P1 F3 1.892(12) 6_565 ? P1 F2 1.980(10) 6_565 ? C2 C3 1.301(10) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 N4 1.396(10) 6_565 ? C5 C5 1.33(3) 6_565 ? C5 C6 1.355(15) . ? C5 N4 1.735(13) 6_565 ? C5 C6 1.927(17) 6_565 ? C5 H5 0.9300 . ? C6 C7 1.375(14) . ? C6 C6 1.41(3) 6_565 ? C6 C7 1.799(16) 6_565 ? C6 C5 1.927(17) 6_565 ? C6 H6 0.9300 . ? C7 C7 0.96(2) 6_565 ? C7 C6 1.799(16) 6_565 ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.309(11) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C13 1.03(2) 6_565 ? C13 C14 1.341(14) . ? C13 C14 1.698(15) 6_565 ? C13 H13 0.9300 . ? C14 C14 1.05(2) 6_565 ? C14 C15 1.390(13) . ? C14 C15 1.641(14) 6_565 ? C14 C13 1.698(15) 6_565 ? C14 H14 0.9300 . ? C15 C15 0.72(2) 6_565 ? C15 C14 1.641(14) 6_565 ? C15 H15 0.9300 . ? C16 C16 0.87(2) 6_565 ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Cu1 C1 178.6(3) . . ? F6 F1 P1 36.5(8) 6_565 . ? F6 F2 P1 34.8(9) 6_565 . ? F6 F2 F2 101.6(11) 6_565 6_565 ? P1 F2 F2 75.1(5) . 6_565 ? F6 F2 P1 55.7(10) 6_565 6_565 ? P1 F2 P1 25.1(3) . 6_565 ? F2 F2 P1 50.1(3) 6_565 6_565 ? F6 F3 F3 106.4(10) 6_565 6_565 ? F6 F3 P1 36.4(7) 6_565 . ? F3 F3 P1 80.5(5) 6_565 . ? F6 F3 P1 58.2(8) 6_565 6_565 ? F3 F3 P1 53.6(4) 6_565 6_565 ? P1 F3 P1 26.9(3) . 6_565 ? P1 F4 P1 33.3(3) 6_565 . ? P1 F5 P1 32.6(3) . 6_565 ? P1 F6 F2 102.3(17) 6_565 6_565 ? P1 F6 F3 86.5(13) 6_565 6_565 ? F2 F6 F3 131.9(16) 6_565 6_565 ? P1 F6 F1 74.1(12) 6_565 6_565 ? F2 F6 F1 119.0(14) 6_565 6_565 ? F3 F6 F1 108.9(12) 6_565 6_565 ? P1 F6 P1 23.0(7) 6_565 . ? F2 F6 P1 90.7(13) 6_565 . ? F3 F6 P1 79.4(10) 6_565 . ? F1 F6 P1 97.1(11) 6_565 . ? C1 N1 C3 111.2(5) . . ? C1 N1 C4 125.6(5) . . ? C3 N1 C4 123.1(6) . . ? C1 N2 C2 112.6(6) . . ? C1 N2 C8 122.8(6) . . ? C2 N2 C8 124.6(6) . . ? C4 N3 C7 114.6(7) . 6_565 ? C4 N3 C7 114.6(7) . . ? C7 N3 C7 39.7(10) 6_565 . ? N4 N4 C5 98.7(7) 6_565 . ? N4 N4 C4 70.5(3) 6_565 . ? C5 N4 C4 115.8(8) . . ? N4 N4 C5 49.3(5) 6_565 6_565 ? C5 N4 C5 49.4(10) . 6_565 ? C4 N4 C5 94.5(6) . 6_565 ? C9 N5 C11 112.1(6) . . ? C9 N5 C12 125.8(5) . . ? C11 N5 C12 122.1(6) . . ? C9 N6 C10 112.4(6) . . ? C9 N6 C16 123.2(6) . 6_565 ? C10 N6 C16 121.2(6) . 6_565 ? C9 N6 C16 123.2(6) . . ? C10 N6 C16 121.2(6) . . ? C16 N6 C16 33.4(9) 6_565 . ? C12 N7 C15 114.4(6) . . ? C12 N7 C15 114.4(6) . 6_565 ? C15 N7 C15 30.5(10) . 6_565 ? C12 N8 C13 112.1(7) . . ? C12 N8 C13 112.1(7) . 6_565 ? C13 N8 C13 42.4(9) . 6_565 ? P1 P1 F6 132.7(11) 6_565 6_565 ? P1 P1 F1 157.9(6) 6_565 . ? F6 P1 F1 69.4(12) 6_565 . ? P1 P1 F4 73.37(16) 6_565 . ? F6 P1 F4 137.3(11) 6_565 . ? F1 P1 F4 90.3(6) . . ? P1 P1 F3 99.5(5) 6_565 . ? F6 P1 F3 57.1(10) 6_565 . ? F1 P1 F3 95.1(8) . . ? F4 P1 F3 89.6(5) . . ? P1 P1 F5 73.69(16) 6_565 . ? F6 P1 F5 124.1(11) 6_565 . ? F1 P1 F5 92.9(6) . . ? F4 P1 F5 92.9(5) . . ? F3 P1 F5 171.7(6) . . ? P1 P1 F2 104.9(5) 6_565 . ? F6 P1 F2 42.9(10) 6_565 . ? F1 P1 F2 91.8(7) . . ? F4 P1 F2 177.6(5) . . ? F3 P1 F2 89.2(6) . . ? F5 P1 F2 88.0(5) . . ? P1 P1 F6 24.4(5) 6_565 . ? F6 P1 F6 108.3(16) 6_565 . ? F1 P1 F6 177.2(8) . . ? F4 P1 F6 92.5(5) . . ? F3 P1 F6 84.7(8) . . ? F5 P1 F6 87.2(6) . . ? F2 P1 F6 85.4(7) . . ? P1 P1 F3 53.6(4) 6_565 6_565 ? F6 P1 F3 92.8(11) 6_565 6_565 ? F1 P1 F3 138.3(7) . 6_565 ? F4 P1 F3 77.6(5) . 6_565 ? F3 P1 F3 45.9(9) . 6_565 ? F5 P1 F3 127.1(5) . 6_565 ? F2 P1 F3 100.1(5) . 6_565 ? F6 P1 F3 42.4(6) . 6_565 ? P1 P1 F2 50.1(3) 6_565 6_565 ? F6 P1 F2 89.5(11) 6_565 6_565 ? F1 P1 F2 143.9(6) . 6_565 ? F4 P1 F2 123.4(4) . 6_565 ? F3 P1 F2 97.4(5) . 6_565 ? F5 P1 F2 74.6(4) . 6_565 ? F2 P1 F2 54.8(8) . 6_565 ? F6 P1 F2 33.6(6) . 6_565 ? F3 P1 F2 68.7(5) 6_565 6_565 ? N2 C1 N1 102.5(5) . . ? N2 C1 Cu1 127.4(5) . . ? N1 C1 Cu1 130.1(4) . . ? C3 C2 N2 107.6(6) . . ? C3 C2 H2 126.2 . . ? N2 C2 H2 126.2 . . ? C2 C3 N1 106.1(6) . . ? C2 C3 H3 127.0 . . ? N1 C3 H3 127.0 . . ? N3 C4 N4 125.0(7) . . ? N3 C4 N4 125.0(7) . 6_565 ? N4 C4 N4 38.9(7) . 6_565 ? N3 C4 N1 118.1(6) . . ? N4 C4 N1 112.9(6) . . ? N4 C4 N1 112.9(6) 6_565 . ? N4 C5 C5 81.3(7) . 6_565 ? N4 C5 C6 123.2(10) . . ? C5 C5 C6 91.5(8) 6_565 . ? N4 C5 N4 32.0(6) . 6_565 ? C5 C5 N4 49.3(5) 6_565 6_565 ? C6 C5 N4 115.7(9) . 6_565 ? N4 C5 C6 105.9(8) . 6_565 ? C5 C5 C6 44.7(5) 6_565 6_565 ? C6 C5 C6 46.9(10) . 6_565 ? N4 C5 C6 80.2(7) 6_565 6_565 ? N4 C5 H5 118.4 . . ? C5 C5 H5 97.5 6_565 . ? C6 C5 H5 118.4 . . ? N4 C5 H5 115.8 6_565 . ? C6 C5 H5 115.5 6_565 . ? C5 C6 C7 116.9(10) . . ? C5 C6 C6 88.5(8) . 6_565 ? C7 C6 C6 80.6(8) . 6_565 ? C5 C6 C7 109.4(9) . 6_565 ? C7 C6 C7 31.6(8) . 6_565 ? C6 C6 C7 48.9(5) 6_565 6_565 ? C5 C6 C5 43.8(9) . 6_565 ? C7 C6 C5 101.8(9) . 6_565 ? C6 C6 C5 44.7(5) 6_565 6_565 ? C7 C6 C5 77.2(7) 6_565 6_565 ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C6 C6 H6 100.6 6_565 . ? C7 C6 H6 119.8 6_565 . ? C5 C6 H6 119.6 6_565 . ? C7 C7 C6 99.4(8) 6_565 . ? C7 C7 N3 70.2(5) 6_565 . ? C6 C7 N3 122.1(10) . . ? C7 C7 C6 48.9(5) 6_565 6_565 ? C6 C7 C6 50.5(10) . 6_565 ? N3 C7 C6 98.1(8) . 6_565 ? C7 C7 H7 100.4 6_565 . ? C6 C7 H7 118.9 . . ? N3 C7 H7 118.9 . . ? C6 C7 H7 120.7 6_565 . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N6 C9 N5 102.4(6) . . ? N6 C9 Cu1 128.8(5) . . ? N5 C9 Cu1 128.8(5) . . ? C11 C10 N6 107.6(6) . . ? C11 C10 H10 126.2 . . ? N6 C10 H10 126.2 . . ? C10 C11 N5 105.5(6) . . ? C10 C11 H11 127.3 . . ? N5 C11 H11 127.3 . . ? N8 C12 N7 128.6(7) . . ? N8 C12 N5 114.8(6) . . ? N7 C12 N5 116.6(6) . . ? C13 C13 C14 90.4(7) 6_565 . ? C13 C13 N8 68.8(5) 6_565 . ? C14 C13 N8 121.6(9) . . ? C13 C13 C14 52.2(5) 6_565 6_565 ? C14 C13 C14 38.2(9) . 6_565 ? N8 C13 C14 100.9(7) . 6_565 ? C13 C13 H13 111.4 6_565 . ? C14 C13 H13 119.2 . . ? N8 C13 H13 119.2 . . ? C14 C13 H13 127.6 6_565 . ? C14 C14 C13 89.6(7) 6_565 . ? C14 C14 C15 83.2(7) 6_565 . ? C13 C14 C15 116.7(9) . . ? C14 C14 C15 57.3(5) 6_565 6_565 ? C13 C14 C15 112.2(9) . 6_565 ? C15 C14 C15 25.9(9) . 6_565 ? C14 C14 C13 52.2(5) 6_565 6_565 ? C13 C14 C13 37.4(9) . 6_565 ? C15 C14 C13 106.5(9) . 6_565 ? C15 C14 C13 88.3(8) 6_565 6_565 ? C14 C14 H14 96.8 6_565 . ? C13 C14 H14 121.6 . . ? C15 C14 H14 121.7 . . ? C15 C14 H14 119.8 6_565 . ? C13 C14 H14 119.1 6_565 . ? C15 C15 N7 74.7(5) 6_565 . ? C15 C15 C14 96.8(7) 6_565 . ? N7 C15 C14 121.9(9) . . ? C15 C15 C14 57.3(5) 6_565 6_565 ? N7 C15 C14 106.2(8) . 6_565 ? C14 C15 C14 39.5(9) . 6_565 ? C15 C15 H15 98.6 6_565 . ? N7 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C14 C15 H15 120.5 6_565 . ? C16 C16 N6 73.3(4) 6_565 . ? C16 C16 H16A 88.3 6_565 . ? N6 C16 H16A 109.5 . . ? C16 C16 H16B 52.0 6_565 . ? N6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C16 C16 H16C 158.9 6_565 . ? N6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F6 F1 P1 P1 176.9(15) 6_565 . . 6_565 ? F6 F1 P1 F4 -141.6(11) 6_565 . . . ? F6 F1 P1 F3 -52.0(11) 6_565 . . . ? F6 F1 P1 F5 125.5(11) 6_565 . . . ? F6 F1 P1 F2 37.4(11) 6_565 . . . ? F6 F1 P1 F6 33(18) 6_565 . . . ? F6 F1 P1 F3 -70.0(13) 6_565 . . 6_565 ? F6 F1 P1 F2 57.9(15) 6_565 . . 6_565 ? P1 F4 P1 F6 136.0(16) 6_565 . . 6_565 ? P1 F4 P1 F1 -164.9(6) 6_565 . . . ? P1 F4 P1 F3 100.0(5) 6_565 . . . ? P1 F4 P1 F5 -72.0(2) 6_565 . . . ? P1 F4 P1 F2 41(13) 6_565 . . . ? P1 F4 P1 F6 15.3(6) 6_565 . . . ? P1 F4 P1 F3 55.4(4) 6_565 . . 6_565 ? P1 F4 P1 F2 1.5(5) 6_565 . . 6_565 ? F6 F3 P1 P1 -135.2(12) 6_565 . . 6_565 ? F3 F3 P1 P1 0.000(6) 6_565 . . 6_565 ? F3 F3 P1 F6 135.2(13) 6_565 . . 6_565 ? P1 F3 P1 F6 135.2(13) 6_565 . . 6_565 ? F6 F3 P1 F1 61.5(13) 6_565 . . . ? F3 F3 P1 F1 -163.3(5) 6_565 . . . ? P1 F3 P1 F1 -163.3(5) 6_565 . . . ? F6 F3 P1 F4 151.7(13) 6_565 . . . ? F3 F3 P1 F4 -73.06(18) 6_565 . . . ? P1 F3 P1 F4 -73.06(18) 6_565 . . . ? F6 F3 P1 F5 -101(4) 6_565 . . . ? F3 F3 P1 F5 35(4) 6_565 . . . ? P1 F3 P1 F5 35(4) 6_565 . . . ? F6 F3 P1 F2 -30.3(13) 6_565 . . . ? F3 F3 P1 F2 104.9(5) 6_565 . . . ? P1 F3 P1 F2 104.9(5) 6_565 . . . ? F6 F3 P1 F6 -115.8(17) 6_565 . . . ? F3 F3 P1 F6 19.5(5) 6_565 . . . ? P1 F3 P1 F6 19.5(5) 6_565 . . . ? F6 F3 P1 F3 -135.2(12) 6_565 . . 6_565 ? P1 F3 P1 F3 0.000(4) 6_565 . . 6_565 ? F6 F3 P1 F2 -84.6(13) 6_565 . . 6_565 ? F3 F3 P1 F2 50.6(3) 6_565 . . 6_565 ? P1 F3 P1 F2 50.6(3) 6_565 . . 6_565 ? P1 F5 P1 F6 -130.9(13) 6_565 . . 6_565 ? P1 F5 P1 F1 162.2(5) 6_565 . . . ? P1 F5 P1 F4 71.7(2) 6_565 . . . ? P1 F5 P1 F3 -36(4) 6_565 . . . ? P1 F5 P1 F2 -106.1(5) 6_565 . . . ? P1 F5 P1 F6 -20.6(5) 6_565 . . . ? P1 F5 P1 F3 -5.0(6) 6_565 . . 6_565 ? P1 F5 P1 F2 -52.2(3) 6_565 . . 6_565 ? F6 F2 P1 P1 138.1(16) 6_565 . . 6_565 ? F2 F2 P1 P1 0.000(2) 6_565 . . 6_565 ? F2 F2 P1 F6 -138.1(16) 6_565 . . 6_565 ? P1 F2 P1 F6 -138.1(16) 6_565 . . 6_565 ? F6 F2 P1 F1 -56.6(16) 6_565 . . . ? F2 F2 P1 F1 165.4(6) 6_565 . . . ? P1 F2 P1 F1 165.4(6) 6_565 . . . ? F6 F2 P1 F4 97(13) 6_565 . . . ? F2 F2 P1 F4 -41(13) 6_565 . . . ? P1 F2 P1 F4 -41(13) 6_565 . . . ? F6 F2 P1 F3 38.5(16) 6_565 . . . ? F2 F2 P1 F3 -99.6(5) 6_565 . . . ? P1 F2 P1 F3 -99.6(5) 6_565 . . . ? F6 F2 P1 F5 -149.4(16) 6_565 . . . ? F2 F2 P1 F5 72.5(2) 6_565 . . . ? P1 F2 P1 F5 72.5(2) 6_565 . . . ? F6 F2 P1 F6 123(2) 6_565 . . . ? F2 F2 P1 F6 -14.8(6) 6_565 . . . ? P1 F2 P1 F6 -14.8(6) 6_565 . . . ? F6 F2 P1 F3 83.3(17) 6_565 . . 6_565 ? F2 F2 P1 F3 -54.8(4) 6_565 . . 6_565 ? P1 F2 P1 F3 -54.8(4) 6_565 . . 6_565 ? F6 F2 P1 F2 138.1(16) 6_565 . . 6_565 ? P1 F2 P1 F2 0.000(2) 6_565 . . 6_565 ? F2 F6 P1 P1 -120.9(19) 6_565 . . 6_565 ? F3 F6 P1 P1 106.5(15) 6_565 . . 6_565 ? F1 F6 P1 P1 -1.5(8) 6_565 . . 6_565 ? P1 F6 P1 F6 180.00(2) 6_565 . . 6_565 ? F2 F6 P1 F6 59.1(19) 6_565 . . 6_565 ? F3 F6 P1 F6 -73.5(15) 6_565 . . 6_565 ? F1 F6 P1 F6 178.5(8) 6_565 . . 6_565 ? P1 F6 P1 F1 147(18) 6_565 . . . ? F2 F6 P1 F1 26(19) 6_565 . . . ? F3 F6 P1 F1 -106(18) 6_565 . . . ? F1 F6 P1 F1 146(18) 6_565 . . . ? P1 F6 P1 F4 -37.9(13) 6_565 . . . ? F2 F6 P1 F4 -158.8(10) 6_565 . . . ? F3 F6 P1 F4 68.6(8) 6_565 . . . ? F1 F6 P1 F4 -39.4(9) 6_565 . . . ? P1 F6 P1 F3 -127.3(12) 6_565 . . . ? F2 F6 P1 F3 111.8(11) 6_565 . . . ? F3 F6 P1 F3 -20.8(7) 6_565 . . . ? F1 F6 P1 F3 -128.8(9) 6_565 . . . ? P1 F6 P1 F5 54.9(13) 6_565 . . . ? F2 F6 P1 F5 -66.0(10) 6_565 . . . ? F3 F6 P1 F5 161.4(9) 6_565 . . . ? F1 F6 P1 F5 53.4(9) 6_565 . . . ? P1 F6 P1 F2 143.2(12) 6_565 . . . ? F2 F6 P1 F2 22.2(9) 6_565 . . . ? F3 F6 P1 F2 -110.4(9) 6_565 . . . ? F1 F6 P1 F2 141.6(9) 6_565 . . . ? P1 F6 P1 F3 -106.5(15) 6_565 . . 6_565 ? F2 F6 P1 F3 132.6(15) 6_565 . . 6_565 ? F1 F6 P1 F3 -108.0(12) 6_565 . . 6_565 ? P1 F6 P1 F2 120.9(19) 6_565 . . 6_565 ? F3 F6 P1 F2 -132.6(15) 6_565 . . 6_565 ? F1 F6 P1 F2 119.4(15) 6_565 . . 6_565 ? C2 N2 C1 N1 0.000(1) . . . . ? C8 N2 C1 N1 180.000(1) . . . . ? C2 N2 C1 Cu1 180.000(1) . . . . ? C8 N2 C1 Cu1 0.000(2) . . . . ? C3 N1 C1 N2 0.000(1) . . . . ? C4 N1 C1 N2 180.000(1) . . . . ? C3 N1 C1 Cu1 180.000(1) . . . . ? C4 N1 C1 Cu1 0.000(2) . . . . ? C9 Cu1 C1 N2 180.00(3) . . . . ? C9 Cu1 C1 N1 0.00(3) . . . . ? C1 N2 C2 C3 0.000(2) . . . . ? C8 N2 C2 C3 180.000(2) . . . . ? N2 C2 C3 N1 0.000(1) . . . . ? C1 N1 C3 C2 0.000(2) . . . . ? C4 N1 C3 C2 180.000(2) . . . . ? C7 N3 C4 N4 -45.9(7) 6_565 . . . ? C7 N3 C4 N4 -2.1(8) . . . . ? C7 N3 C4 N4 2.1(8) 6_565 . . 6_565 ? C7 N3 C4 N4 45.9(7) . . . 6_565 ? C7 N3 C4 N1 158.1(5) 6_565 . . . ? C7 N3 C4 N1 -158.1(5) . . . . ? N4 N4 C4 N3 104.3(5) 6_565 . . . ? C5 N4 C4 N3 13.9(10) . . . . ? C5 N4 C4 N3 60.5(7) 6_565 . . . ? C5 N4 C4 N4 -90.4(8) . . . 6_565 ? C5 N4 C4 N4 -43.8(6) 6_565 . . 6_565 ? N4 N4 C4 N1 -98.6(3) 6_565 . . . ? C5 N4 C4 N1 171.0(7) . . . . ? C5 N4 C4 N1 -142.4(5) 6_565 . . . ? C1 N1 C4 N3 0.000(2) . . . . ? C3 N1 C4 N3 180.000(2) . . . . ? C1 N1 C4 N4 -158.8(4) . . . . ? C3 N1 C4 N4 21.2(4) . . . . ? C1 N1 C4 N4 158.8(4) . . . 6_565 ? C3 N1 C4 N4 -21.2(4) . . . 6_565 ? N4 N4 C5 C5 0.000(2) 6_565 . . 6_565 ? C4 N4 C5 C5 72.5(6) . . . 6_565 ? N4 N4 C5 C6 -86.1(12) 6_565 . . . ? C4 N4 C5 C6 -13.6(16) . . . . ? C5 N4 C5 C6 -86.1(12) 6_565 . . . ? C4 N4 C5 N4 72.5(6) . . . 6_565 ? C5 N4 C5 N4 0.000(3) 6_565 . . 6_565 ? N4 N4 C5 C6 -37.6(7) 6_565 . . 6_565 ? C4 N4 C5 C6 34.9(10) . . . 6_565 ? C5 N4 C5 C6 -37.6(7) 6_565 . . 6_565 ? N4 C5 C6 C7 2(2) . . . . ? C5 C5 C6 C7 -78.6(11) 6_565 . . . ? N4 C5 C6 C7 -33.9(16) 6_565 . . . ? C6 C5 C6 C7 -78.6(11) 6_565 . . . ? N4 C5 C6 C6 80.6(12) . . . 6_565 ? C5 C5 C6 C6 0.000(5) 6_565 . . 6_565 ? N4 C5 C6 C6 44.7(8) 6_565 . . 6_565 ? N4 C5 C6 C7 35.5(16) . . . 6_565 ? C5 C5 C6 C7 -45.1(7) 6_565 . . 6_565 ? N4 C5 C6 C7 -0.4(13) 6_565 . . 6_565 ? C6 C5 C6 C7 -45.1(7) 6_565 . . 6_565 ? N4 C5 C6 C5 80.6(12) . . . 6_565 ? N4 C5 C6 C5 44.7(8) 6_565 . . 6_565 ? C6 C5 C6 C5 0.000(8) 6_565 . . 6_565 ? C5 C6 C7 C7 83.4(12) . . . 6_565 ? C6 C6 C7 C7 0.000(7) 6_565 . . 6_565 ? C5 C6 C7 C7 39.5(7) 6_565 . . 6_565 ? C5 C6 C7 N3 10.9(19) . . . . ? C6 C6 C7 N3 -72.4(9) 6_565 . . . ? C7 C6 C7 N3 -72.4(9) 6_565 . . . ? C5 C6 C7 N3 -32.9(13) 6_565 . . . ? C5 C6 C7 C6 83.4(12) . . . 6_565 ? C7 C6 C7 C6 0.000(9) 6_565 . . 6_565 ? C5 C6 C7 C6 39.5(7) 6_565 . . 6_565 ? C4 N3 C7 C7 -99.5(4) . . . 6_565 ? C4 N3 C7 C6 -10.7(13) . . . . ? C7 N3 C7 C6 88.8(12) 6_565 . . . ? C4 N3 C7 C6 -58.7(7) . . . 6_565 ? C7 N3 C7 C6 40.8(7) 6_565 . . 6_565 ? C10 N6 C9 N5 0.0 . . . . ? C16 N6 C9 N5 159.9(5) 6_565 . . . ? C16 N6 C9 N5 -159.9(5) . . . . ? C10 N6 C9 Cu1 180.0 . . . . ? C16 N6 C9 Cu1 -20.1(5) 6_565 . . . ? C16 N6 C9 Cu1 20.1(5) . . . . ? C11 N5 C9 N6 0.0 . . . . ? C12 N5 C9 N6 180.0 . . . . ? C11 N5 C9 Cu1 180.0 . . . . ? C12 N5 C9 Cu1 0.0 . . . . ? C1 Cu1 C9 N6 0.000(17) . . . . ? C1 Cu1 C9 N5 180.000(16) . . . . ? C9 N6 C10 C11 0.0 . . . . ? C16 N6 C10 C11 -160.4(5) 6_565 . . . ? C16 N6 C10 C11 160.4(5) . . . . ? N6 C10 C11 N5 0.0 . . . . ? C9 N5 C11 C10 0.0 . . . . ? C12 N5 C11 C10 180.0 . . . . ? C13 N8 C12 N7 -23.0(5) . . . . ? C13 N8 C12 N7 23.0(5) 6_565 . . . ? C13 N8 C12 N5 157.0(5) . . . . ? C13 N8 C12 N5 -157.0(5) 6_565 . . . ? C15 N7 C12 N8 16.8(5) . . . . ? C15 N7 C12 N8 -16.8(5) 6_565 . . . ? C15 N7 C12 N5 -163.2(5) . . . . ? C15 N7 C12 N5 163.2(5) 6_565 . . . ? C9 N5 C12 N8 180.0 . . . . ? C11 N5 C12 N8 0.0 . . . . ? C9 N5 C12 N7 0.0 . . . . ? C11 N5 C12 N7 180.0 . . . . ? C12 N8 C13 C13 99.1(4) . . . 6_565 ? C12 N8 C13 C14 22.4(12) . . . . ? C13 N8 C13 C14 -76.7(10) 6_565 . . . ? C12 N8 C13 C14 57.2(7) . . . 6_565 ? C13 N8 C13 C14 -41.8(7) 6_565 . . 6_565 ? C13 C13 C14 C14 0.000(2) 6_565 . . 6_565 ? N8 C13 C14 C14 65.1(9) . . . 6_565 ? C13 C13 C14 C15 -82.2(10) 6_565 . . . ? N8 C13 C14 C15 -17.1(16) . . . . ? C14 C13 C14 C15 -82.2(10) 6_565 . . . ? C13 C13 C14 C15 -54.1(7) 6_565 . . 6_565 ? N8 C13 C14 C15 11.0(14) . . . 6_565 ? C14 C13 C14 C15 -54.1(7) 6_565 . . 6_565 ? N8 C13 C14 C13 65.1(9) . . . 6_565 ? C14 C13 C14 C13 0.000(3) 6_565 . . 6_565 ? C12 N7 C15 C15 -97.1(3) . . . 6_565 ? C12 N7 C15 C14 -8.6(12) . . . . ? C15 N7 C15 C14 88.5(10) 6_565 . . . ? C12 N7 C15 C14 -48.6(8) . . . 6_565 ? C15 N7 C15 C14 48.5(7) 6_565 . . 6_565 ? C14 C14 C15 C15 0.000(3) 6_565 . . 6_565 ? C13 C14 C15 C15 86.1(10) . . . 6_565 ? C13 C14 C15 C15 47.2(7) 6_565 . . 6_565 ? C14 C14 C15 N7 -76.2(9) 6_565 . . . ? C13 C14 C15 N7 9.9(16) . . . . ? C15 C14 C15 N7 -76.2(9) 6_565 . . . ? C13 C14 C15 N7 -29.0(13) 6_565 . . . ? C13 C14 C15 C14 86.1(10) . . . 6_565 ? C15 C14 C15 C14 0.000(5) 6_565 . . 6_565 ? C13 C14 C15 C14 47.2(7) 6_565 . . 6_565 ? C9 N6 C16 C16 -101.3(4) . . . 6_565 ? C10 N6 C16 C16 100.5(4) . . . 6_565 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.671 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.121 #===END data_090515e _database_code_depnum_ccdc_archive 'CCDC 782457' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H30 Cu3 F18 N12 P3' _chemical_formula_weight 1292.28 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.1414(17) _cell_length_b 14.2973(18) _cell_length_c 14.795(2) _cell_angle_alpha 82.063(2) _cell_angle_beta 62.2200(10) _cell_angle_gamma 66.5580(10) _cell_volume 2424.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 1.518 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6672 _exptl_absorpt_correction_T_max 0.8508 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 12803 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 8436 _reflns_number_gt 5272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SMART' _computing_publication_material 'Bruker SMART' _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^)+(0.0628P)^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 8436 _refine_ls_number_parameters 676 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _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 0.89900(5) 0.17372(5) 0.17325(4) 0.03591(17) Uani 1 1 d . . . Cu2 Cu 0.98001(5) 0.29144(5) 0.19375(4) 0.03798(17) Uani 1 1 d . . . Cu3 Cu 0.89129(5) 0.19784(5) 0.34061(4) 0.03824(17) Uani 1 1 d . . . P1 P 0.75481(13) 0.70938(12) 0.44556(11) 0.0508(4) Uani 1 1 d . . . P2 P 0.22900(16) 0.55681(15) 0.19686(12) 0.0681(5) Uani 1 1 d . . . C27 C 0.8195(4) 0.1125(4) 0.3066(3) 0.0355(11) Uani 1 1 d . . . C1 C 0.9873(4) 0.2494(4) 0.0611(3) 0.0400(12) Uani 1 1 d . . . C14 C 0.9578(4) 0.3033(4) 0.3417(3) 0.0374(11) Uani 1 1 d . . . F5 F 0.7309(3) 0.6633(3) 0.5552(2) 0.0726(10) Uani 1 1 d . . . N4 N 0.8874(4) 0.4331(3) 0.1609(3) 0.0439(10) Uani 1 1 d . . . N10 N 0.7140(3) 0.1274(3) 0.3163(3) 0.0399(10) Uani 1 1 d . . . N6 N 0.8785(3) 0.3608(3) 0.4318(3) 0.0388(10) Uani 1 1 d . . . N5 N 1.0592(3) 0.3040(3) 0.3286(3) 0.0398(10) Uani 1 1 d . . . N12 N 0.7334(3) 0.2378(3) 0.1860(3) 0.0393(10) Uani 1 1 d . . . N11 N 0.9906(3) 0.0538(3) 0.3642(3) 0.0419(10) Uani 1 1 d . . . N1 N 1.0698(3) 0.1792(3) -0.0178(3) 0.0435(11) Uani 1 1 d . . . N9 N 0.8469(3) 0.0248(3) 0.3544(3) 0.0400(10) Uani 1 1 d . . . N2 N 0.9585(4) 0.3376(4) 0.0144(3) 0.0439(11) Uani 1 1 d . . . N3 N 1.0357(4) 0.0465(3) 0.0798(3) 0.0427(10) Uani 1 1 d . . . N8 N 0.7458(4) 0.2918(3) 0.4615(3) 0.0436(10) Uani 1 1 d . . . N7 N 1.1505(3) 0.2522(3) 0.1586(3) 0.0429(10) Uani 1 1 d . . . C35 C 0.6601(4) 0.2050(4) 0.2655(4) 0.0415(12) Uani 1 1 d . . . F1 F 0.8425(3) 0.7475(3) 0.4514(3) 0.0914(12) Uani 1 1 d . . . F12 F 0.3273(5) 0.4628(4) 0.1242(4) 0.162(2) Uani 1 1 d . . . C16 C 1.0438(5) 0.3594(4) 0.4072(4) 0.0507(14) Uani 1 1 d . . . H16 H 1.1012 0.3700 0.4137 0.061 Uiso 1 1 calc R . . C30 C 0.9508(4) -0.0160(4) 0.3639(3) 0.0405(12) Uani 1 1 d . . . F2 F 0.6653(3) 0.6713(3) 0.4428(3) 0.0925(12) Uani 1 1 d . . . F4 F 0.6527(3) 0.8145(3) 0.4984(3) 0.0828(11) Uani 1 1 d . . . C4 C 1.1130(4) 0.0743(4) -0.0012(4) 0.0439(13) Uani 1 1 d . . . C9 C 0.8853(5) 0.4318(4) 0.0718(4) 0.0446(13) Uani 1 1 d . . . C22 C 0.7627(5) 0.3699(4) 0.4833(3) 0.0424(12) Uani 1 1 d . . . C28 C 0.6754(5) 0.0519(4) 0.3713(4) 0.0549(15) Uani 1 1 d . . . H28 H 0.6054 0.0471 0.3884 0.066 Uiso 1 1 calc R . . C15 C 0.9319(5) 0.3946(4) 0.4719(4) 0.0523(14) Uani 1 1 d . . . H15 H 0.8961 0.4342 0.5322 0.063 Uiso 1 1 calc R . . C29 C 0.7587(5) -0.0121(4) 0.3947(4) 0.0522(14) Uani 1 1 d . . . H29 H 0.7580 -0.0705 0.4311 0.063 Uiso 1 1 calc R . . C3 C 1.0898(5) 0.2250(5) -0.1120(4) 0.0544(15) Uani 1 1 d . . . H3 H 1.1420 0.1925 -0.1765 0.065 Uiso 1 1 calc R . . C13 C 0.8160(5) 0.5178(4) 0.2228(4) 0.0545(15) Uani 1 1 d . . . H13 H 0.8153 0.5198 0.2856 0.065 Uiso 1 1 calc R . . F9 F 0.2229(5) 0.6199(4) 0.1030(3) 0.1302(18) Uani 1 1 d . . . C39 C 0.6895(5) 0.3111(4) 0.1341(4) 0.0499(14) Uani 1 1 d . . . H39 H 0.7396 0.3346 0.0782 0.060 Uiso 1 1 calc R . . C31 C 1.0055(5) -0.1186(4) 0.3682(4) 0.0512(14) Uani 1 1 d . . . H31 H 0.9725 -0.1641 0.3704 0.061 Uiso 1 1 calc R . . C2 C 1.0209(5) 0.3223(5) -0.0921(4) 0.0542(15) Uani 1 1 d . . . H2 H 1.0150 0.3713 -0.1397 0.065 Uiso 1 1 calc R . . C8 C 1.0718(5) -0.0514(5) 0.1037(4) 0.0568(15) Uani 1 1 d . . . H8 H 1.0193 -0.0733 0.1589 0.068 Uiso 1 1 calc R . . C17 C 1.1642(4) 0.2602(4) 0.2394(4) 0.0432(12) Uani 1 1 d . . . C36 C 0.5431(5) 0.2433(5) 0.2967(4) 0.0541(14) Uani 1 1 d . . . H36 H 0.4944 0.2194 0.3536 0.065 Uiso 1 1 calc R . . C25 C 0.5478(5) 0.3725(5) 0.5762(5) 0.0726(19) Uani 1 1 d . . . H25 H 0.4735 0.3724 0.6071 0.087 Uiso 1 1 calc R . . C21 C 1.2472(5) 0.2082(4) 0.0723(4) 0.0532(14) Uani 1 1 d . . . H21 H 1.2398 0.1992 0.0152 0.064 Uiso 1 1 calc R . . F3 F 0.7787(4) 0.7552(3) 0.3382(3) 0.1050(14) Uani 1 1 d . . . C24 C 0.5671(6) 0.4505(5) 0.5981(5) 0.078(2) Uani 1 1 d . . . H24 H 0.5063 0.5040 0.6444 0.094 Uiso 1 1 calc R . . C7 C 1.1816(6) -0.1200(5) 0.0506(5) 0.0720(18) Uani 1 1 d . . . H7 H 1.2042 -0.1867 0.0704 0.086 Uiso 1 1 calc R . . C23 C 0.6776(5) 0.4496(4) 0.5512(4) 0.0595(16) Uani 1 1 d . . . H23 H 0.6935 0.5015 0.5653 0.071 Uiso 1 1 calc R . . C34 C 1.0930(5) 0.0188(4) 0.3653(4) 0.0515(14) Uani 1 1 d . . . H34 H 1.1239 0.0661 0.3633 0.062 Uiso 1 1 calc R . . C11 C 0.7429(6) 0.5986(5) 0.1057(5) 0.0716(18) Uani 1 1 d . . . H11 H 0.6933 0.6540 0.0876 0.086 Uiso 1 1 calc R . . C26 C 0.6382(5) 0.2942(5) 0.5083(4) 0.0600(16) Uani 1 1 d . . . H26 H 0.6242 0.2409 0.4944 0.072 Uiso 1 1 calc R . . C33 C 1.1544(5) -0.0806(5) 0.3691(4) 0.0623(16) Uani 1 1 d . . . H33 H 1.2243 -0.1007 0.3716 0.075 Uiso 1 1 calc R . . C5 C 1.2248(5) 0.0100(5) -0.0604(4) 0.0619(16) Uani 1 1 d . . . H5 H 1.2754 0.0328 -0.1165 0.074 Uiso 1 1 calc R . . C37 C 0.5009(5) 0.3171(5) 0.2417(4) 0.0626(16) Uani 1 1 d . . . H37 H 0.4224 0.3431 0.2598 0.075 Uiso 1 1 calc R . . C38 C 0.5737(5) 0.3539(4) 0.1594(4) 0.0549(14) Uani 1 1 d . . . H38 H 0.5454 0.4056 0.1223 0.066 Uiso 1 1 calc R . . C32 C 1.1106(5) -0.1525(5) 0.3694(4) 0.0638(16) Uani 1 1 d . . . H32 H 1.1515 -0.2218 0.3704 0.077 Uiso 1 1 calc R . . C20 C 1.3554(5) 0.1761(5) 0.0643(5) 0.0677(17) Uani 1 1 d . . . H20 H 1.4203 0.1475 0.0028 0.081 Uiso 1 1 calc R . . F11 F 0.2309(4) 0.4881(4) 0.2915(3) 0.1204(16) Uani 1 1 d . . . F8 F 0.1401(4) 0.5166(4) 0.1978(3) 0.1169(16) Uani 1 1 d . . . C10 C 0.8161(5) 0.5129(5) 0.0399(4) 0.0607(16) Uani 1 1 d . . . H10 H 0.8186 0.5098 -0.0236 0.073 Uiso 1 1 calc R . . F6 F 0.8535(4) 0.6048(3) 0.3944(3) 0.1202(16) Uani 1 1 d . . . C18 C 1.2697(5) 0.2282(5) 0.2393(4) 0.0579(15) Uani 1 1 d . . . H18 H 1.2753 0.2344 0.2982 0.070 Uiso 1 1 calc R . . F10 F 0.1279(5) 0.6443(4) 0.2742(4) 0.153(2) Uani 1 1 d . . . F7 F 0.3153(5) 0.5928(5) 0.1971(5) 0.175(3) Uani 1 1 d . . . C19 C 1.3660(5) 0.1869(5) 0.1490(5) 0.0706(18) Uani 1 1 d . . . H19 H 1.4390 0.1660 0.1453 0.085 Uiso 1 1 calc R . . C12 C 0.7432(5) 0.6023(5) 0.1972(5) 0.0651(16) Uani 1 1 d . . . H12 H 0.6956 0.6604 0.2414 0.078 Uiso 1 1 calc R . . P3 P 0.48994(16) 0.92545(16) 0.27168(15) 0.0757(5) Uani 1 1 d . . . F17 F 0.5205(4) 1.0198(4) 0.2626(4) 0.1371(19) Uani 1 1 d . . . F15 F 0.4583(5) 0.8331(5) 0.2859(7) 0.217(4) Uani 1 1 d . . . F14 F 0.4810(7) 0.9508(5) 0.1748(5) 0.196(3) Uani 1 1 d . . . F18 F 0.6196(4) 0.8562(4) 0.2114(5) 0.166(3) Uani 1 1 d . . . F16 F 0.3604(4) 0.9964(4) 0.3301(4) 0.152(2) Uani 1 1 d . . . C6 C 1.2584(6) -0.0885(5) -0.0333(5) 0.0767(19) Uani 1 1 d . . . H6 H 1.3333 -0.1345 -0.0714 0.092 Uiso 1 1 calc R . . F13 F 0.4980(6) 0.9039(7) 0.3724(5) 0.232(4) 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 0.0360(4) 0.0452(4) 0.0306(3) 0.0045(3) -0.0127(3) -0.0228(3) Cu2 0.0430(4) 0.0477(4) 0.0341(3) 0.0099(3) -0.0200(3) -0.0268(3) Cu3 0.0483(4) 0.0394(4) 0.0334(3) 0.0054(3) -0.0175(3) -0.0249(3) P1 0.0588(10) 0.0522(10) 0.0456(8) 0.0116(7) -0.0230(7) -0.0286(9) P2 0.0696(12) 0.0753(12) 0.0556(10) 0.0010(9) -0.0356(9) -0.0143(11) C27 0.037(3) 0.042(3) 0.032(2) 0.001(2) -0.016(2) -0.019(3) C1 0.041(3) 0.050(3) 0.038(3) 0.001(3) -0.016(2) -0.027(3) C14 0.046(3) 0.033(3) 0.040(3) 0.013(2) -0.023(2) -0.020(3) F5 0.098(3) 0.087(3) 0.067(2) 0.0380(19) -0.051(2) -0.062(2) N4 0.057(3) 0.047(3) 0.040(2) 0.013(2) -0.026(2) -0.029(3) N10 0.035(2) 0.048(3) 0.040(2) 0.006(2) -0.0137(19) -0.025(2) N6 0.051(3) 0.040(3) 0.035(2) 0.0046(19) -0.021(2) -0.026(2) N5 0.044(3) 0.044(3) 0.042(2) 0.009(2) -0.024(2) -0.023(2) N12 0.039(2) 0.047(3) 0.041(2) 0.006(2) -0.019(2) -0.024(2) N11 0.049(3) 0.045(3) 0.041(2) 0.010(2) -0.023(2) -0.027(2) N1 0.042(3) 0.058(3) 0.034(2) 0.003(2) -0.012(2) -0.029(3) N9 0.046(3) 0.043(3) 0.039(2) 0.008(2) -0.019(2) -0.025(2) N2 0.047(3) 0.061(3) 0.034(2) 0.012(2) -0.021(2) -0.030(3) N3 0.046(3) 0.048(3) 0.036(2) 0.000(2) -0.016(2) -0.022(2) N8 0.046(3) 0.047(3) 0.037(2) -0.001(2) -0.011(2) -0.026(2) N7 0.041(3) 0.048(3) 0.047(2) 0.008(2) -0.022(2) -0.024(2) C35 0.039(3) 0.048(3) 0.041(3) 0.002(2) -0.019(2) -0.019(3) F1 0.090(3) 0.096(3) 0.131(3) 0.053(3) -0.068(3) -0.067(3) F12 0.136(5) 0.147(5) 0.106(4) -0.035(3) -0.033(3) 0.025(4) C16 0.065(4) 0.058(4) 0.052(3) 0.006(3) -0.035(3) -0.035(3) C30 0.047(3) 0.040(3) 0.038(3) 0.006(2) -0.020(2) -0.019(3) F2 0.119(3) 0.112(3) 0.103(3) 0.027(2) -0.073(3) -0.075(3) F4 0.075(3) 0.060(2) 0.087(2) 0.0063(19) -0.019(2) -0.023(2) C4 0.042(3) 0.057(4) 0.039(3) -0.007(3) -0.013(3) -0.027(3) C9 0.053(3) 0.045(3) 0.046(3) 0.015(3) -0.025(3) -0.030(3) C22 0.056(4) 0.043(3) 0.034(3) 0.006(2) -0.021(3) -0.026(3) C28 0.052(4) 0.063(4) 0.056(3) 0.017(3) -0.019(3) -0.039(3) C15 0.069(4) 0.055(4) 0.047(3) -0.001(3) -0.027(3) -0.034(3) C29 0.060(4) 0.053(4) 0.058(3) 0.021(3) -0.025(3) -0.041(3) C3 0.053(4) 0.080(5) 0.028(3) 0.002(3) -0.009(3) -0.035(4) C13 0.069(4) 0.050(4) 0.050(3) 0.012(3) -0.028(3) -0.030(4) F9 0.189(5) 0.132(4) 0.115(3) 0.073(3) -0.098(4) -0.090(4) C39 0.048(3) 0.056(4) 0.051(3) 0.010(3) -0.024(3) -0.024(3) C31 0.061(4) 0.045(4) 0.056(3) 0.009(3) -0.031(3) -0.025(3) C2 0.061(4) 0.074(4) 0.034(3) 0.016(3) -0.020(3) -0.037(4) C8 0.066(4) 0.052(4) 0.043(3) -0.006(3) -0.016(3) -0.020(4) C17 0.047(3) 0.046(3) 0.052(3) 0.012(3) -0.030(3) -0.026(3) C36 0.040(3) 0.064(4) 0.058(3) 0.004(3) -0.018(3) -0.026(3) C25 0.055(4) 0.077(5) 0.071(4) -0.017(4) -0.005(3) -0.034(4) C21 0.049(4) 0.064(4) 0.049(3) 0.003(3) -0.020(3) -0.026(3) F3 0.121(3) 0.132(4) 0.056(2) 0.041(2) -0.035(2) -0.059(3) C24 0.064(5) 0.064(4) 0.073(4) -0.020(4) -0.002(4) -0.019(4) C7 0.078(5) 0.053(4) 0.065(4) -0.014(3) -0.024(4) -0.010(4) C23 0.066(4) 0.049(4) 0.057(3) -0.006(3) -0.016(3) -0.027(3) C34 0.056(4) 0.054(4) 0.056(3) 0.015(3) -0.030(3) -0.030(3) C11 0.076(5) 0.051(4) 0.086(5) 0.023(4) -0.043(4) -0.022(4) C26 0.061(4) 0.065(4) 0.050(3) -0.010(3) -0.009(3) -0.036(4) C33 0.053(4) 0.064(4) 0.076(4) 0.013(3) -0.039(3) -0.020(4) C5 0.047(4) 0.069(5) 0.058(4) -0.014(3) -0.004(3) -0.029(4) C37 0.037(3) 0.068(4) 0.075(4) 0.006(3) -0.023(3) -0.018(3) C38 0.051(4) 0.052(4) 0.069(4) 0.010(3) -0.036(3) -0.018(3) C32 0.067(4) 0.050(4) 0.070(4) 0.013(3) -0.034(3) -0.018(4) C20 0.043(4) 0.078(5) 0.070(4) -0.005(3) -0.017(3) -0.020(4) F11 0.145(4) 0.135(4) 0.087(3) 0.026(3) -0.076(3) -0.037(4) F8 0.141(4) 0.156(5) 0.111(3) 0.048(3) -0.085(3) -0.090(4) C10 0.073(4) 0.060(4) 0.062(4) 0.019(3) -0.042(4) -0.028(4) F6 0.103(3) 0.069(3) 0.128(4) -0.012(3) -0.020(3) -0.010(3) C18 0.053(4) 0.071(4) 0.063(4) 0.011(3) -0.035(3) -0.027(4) F10 0.159(5) 0.098(4) 0.129(4) -0.038(3) -0.038(4) 0.002(4) F7 0.164(5) 0.252(8) 0.186(6) 0.028(5) -0.093(5) -0.140(6) C19 0.046(4) 0.077(5) 0.088(5) 0.006(4) -0.032(4) -0.021(4) C12 0.072(4) 0.047(4) 0.069(4) 0.011(3) -0.028(4) -0.023(4) P3 0.0613(13) 0.0756(13) 0.0874(13) 0.0257(11) -0.0324(10) -0.0318(11) F17 0.105(4) 0.120(4) 0.191(5) -0.027(4) -0.048(4) -0.058(3) F15 0.135(5) 0.121(5) 0.373(11) 0.065(6) -0.087(6) -0.079(5) F14 0.290(8) 0.139(5) 0.144(5) -0.022(4) -0.148(6) 0.003(5) F18 0.074(3) 0.101(4) 0.223(6) 0.041(4) -0.012(4) -0.018(3) F16 0.059(3) 0.151(5) 0.211(6) 0.004(4) -0.041(3) -0.030(3) C6 0.054(4) 0.067(5) 0.081(5) -0.030(4) -0.011(4) -0.009(4) F13 0.195(7) 0.275(10) 0.143(5) 0.074(6) -0.084(5) -0.023(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 C1 2.033(5) . ? Cu1 C27 2.040(4) . ? Cu1 N12 2.071(4) . ? Cu1 N3 2.088(4) . ? Cu1 Cu3 2.4932(8) . ? Cu1 Cu2 2.4971(8) . ? Cu2 N7 2.057(4) . ? Cu2 N4 2.065(4) . ? Cu2 C1 2.076(4) . ? Cu2 C14 2.083(4) . ? Cu2 Cu3 2.4654(8) . ? Cu3 N8 2.067(4) . ? Cu3 N11 2.072(4) . ? Cu3 C14 2.076(4) . ? Cu3 C27 2.099(4) . ? P1 F6 1.557(4) . ? P1 F3 1.566(3) . ? P1 F1 1.580(3) . ? P1 F4 1.581(4) . ? P1 F2 1.582(3) . ? P1 F5 1.597(3) . ? P2 F7 1.504(5) . ? P2 F10 1.539(5) . ? P2 F12 1.554(5) . ? P2 F9 1.566(4) . ? P2 F8 1.572(4) . ? P2 F11 1.600(4) . ? C27 N10 1.359(5) . ? C27 N9 1.359(6) . ? C1 N2 1.359(6) . ? C1 N1 1.362(6) . ? C14 N5 1.359(5) . ? C14 N6 1.373(6) . ? N4 C9 1.335(6) . ? N4 C13 1.341(7) . ? N10 C28 1.392(6) . ? N10 C35 1.417(6) . ? N6 C15 1.394(6) . ? N6 C22 1.405(6) . ? N5 C16 1.381(6) . ? N5 C17 1.414(6) . ? N12 C35 1.332(6) . ? N12 C39 1.333(6) . ? N11 C30 1.329(6) . ? N11 C34 1.338(6) . ? N1 C3 1.406(6) . ? N1 C4 1.411(7) . ? N9 C29 1.389(6) . ? N9 C30 1.417(6) . ? N2 C2 1.398(6) . ? N2 C9 1.412(7) . ? N3 C4 1.335(6) . ? N3 C8 1.345(7) . ? N8 C26 1.334(6) . ? N8 C22 1.338(6) . ? N7 C17 1.323(6) . ? N7 C21 1.343(6) . ? C35 C36 1.374(7) . ? C16 C15 1.326(7) . ? C16 H16 0.9300 . ? C30 C31 1.368(7) . ? C4 C5 1.373(7) . ? C9 C10 1.378(7) . ? C22 C23 1.361(7) . ? C28 C29 1.335(7) . ? C28 H28 0.9300 . ? C15 H15 0.9300 . ? C29 H29 0.9300 . ? C3 C2 1.319(8) . ? C3 H3 0.9300 . ? C13 C12 1.381(8) . ? C13 H13 0.9300 . ? C39 C38 1.375(7) . ? C39 H39 0.9300 . ? C31 C32 1.376(7) . ? C31 H31 0.9300 . ? C2 H2 0.9300 . ? C8 C7 1.362(8) . ? C8 H8 0.9300 . ? C17 C18 1.375(7) . ? C36 C37 1.359(8) . ? C36 H36 0.9300 . ? C25 C24 1.359(8) . ? C25 C26 1.368(8) . ? C25 H25 0.9300 . ? C21 C20 1.361(7) . ? C21 H21 0.9300 . ? C24 C23 1.378(8) . ? C24 H24 0.9300 . ? C7 C6 1.379(8) . ? C7 H7 0.9300 . ? C23 H23 0.9300 . ? C34 C33 1.349(8) . ? C34 H34 0.9300 . ? C11 C12 1.365(8) . ? C11 C10 1.379(8) . ? C11 H11 0.9300 . ? C26 H26 0.9300 . ? C33 C32 1.394(7) . ? C33 H33 0.9300 . ? C5 C6 1.364(8) . ? C5 H5 0.9300 . ? C37 C38 1.380(7) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C32 H32 0.9300 . ? C20 C19 1.365(8) . ? C20 H20 0.9300 . ? C10 H10 0.9300 . ? C18 C19 1.368(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C12 H12 0.9300 . ? P3 F14 1.480(5) . ? P3 F15 1.515(6) . ? P3 F13 1.528(7) . ? P3 F17 1.544(5) . ? P3 F18 1.554(5) . ? P3 F16 1.555(5) . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 C27 166.44(17) . . ? C1 Cu1 N12 104.58(18) . . ? C27 Cu1 N12 82.06(17) . . ? C1 Cu1 N3 82.17(18) . . ? C27 Cu1 N3 103.50(18) . . ? N12 Cu1 N3 126.91(15) . . ? C1 Cu1 Cu3 112.39(13) . . ? C27 Cu1 Cu3 54.05(12) . . ? N12 Cu1 Cu3 109.39(11) . . ? N3 Cu1 Cu3 116.26(11) . . ? C1 Cu1 Cu2 53.37(13) . . ? C27 Cu1 Cu2 113.11(12) . . ? N12 Cu1 Cu2 117.44(11) . . ? N3 Cu1 Cu2 108.59(11) . . ? Cu3 Cu1 Cu2 59.21(2) . . ? N7 Cu2 N4 120.30(15) . . ? N7 Cu2 C1 103.91(17) . . ? N4 Cu2 C1 81.07(18) . . ? N7 Cu2 C14 82.01(17) . . ? N4 Cu2 C14 107.80(17) . . ? C1 Cu2 C14 165.34(18) . . ? N7 Cu2 Cu3 109.99(11) . . ? N4 Cu2 Cu3 123.12(11) . . ? C1 Cu2 Cu3 111.92(13) . . ? C14 Cu2 Cu3 53.52(12) . . ? N7 Cu2 Cu1 124.86(12) . . ? N4 Cu2 Cu1 104.98(11) . . ? C1 Cu2 Cu1 51.80(12) . . ? C14 Cu2 Cu1 113.79(12) . . ? Cu3 Cu2 Cu1 60.31(2) . . ? N8 Cu3 N11 120.98(15) . . ? N8 Cu3 C14 82.85(17) . . ? N11 Cu3 C14 110.05(17) . . ? N8 Cu3 C27 100.02(16) . . ? N11 Cu3 C27 81.41(17) . . ? C14 Cu3 C27 164.83(17) . . ? N8 Cu3 Cu2 113.57(11) . . ? N11 Cu3 Cu2 120.17(11) . . ? C14 Cu3 Cu2 53.78(12) . . ? C27 Cu3 Cu2 112.20(12) . . ? N8 Cu3 Cu1 123.66(11) . . ? N11 Cu3 Cu1 103.42(11) . . ? C14 Cu3 Cu1 114.21(12) . . ? C27 Cu3 Cu1 51.88(12) . . ? Cu2 Cu3 Cu1 60.47(2) . . ? F6 P1 F3 90.8(2) . . ? F6 P1 F1 90.9(2) . . ? F3 P1 F1 89.6(2) . . ? F6 P1 F4 178.8(2) . . ? F3 P1 F4 89.7(2) . . ? F1 P1 F4 90.1(2) . . ? F6 P1 F2 89.7(3) . . ? F3 P1 F2 91.7(2) . . ? F1 P1 F2 178.5(2) . . ? F4 P1 F2 89.3(2) . . ? F6 P1 F5 89.4(2) . . ? F3 P1 F5 179.5(2) . . ? F1 P1 F5 89.93(18) . . ? F4 P1 F5 90.1(2) . . ? F2 P1 F5 88.74(18) . . ? F7 P2 F10 91.2(4) . . ? F7 P2 F12 91.3(4) . . ? F10 P2 F12 175.7(3) . . ? F7 P2 F9 92.8(3) . . ? F10 P2 F9 92.7(3) . . ? F12 P2 F9 90.7(3) . . ? F7 P2 F8 178.5(3) . . ? F10 P2 F8 89.4(3) . . ? F12 P2 F8 88.0(3) . . ? F9 P2 F8 88.5(2) . . ? F7 P2 F11 91.0(3) . . ? F10 P2 F11 88.3(3) . . ? F12 P2 F11 88.3(3) . . ? F9 P2 F11 176.1(3) . . ? F8 P2 F11 87.7(2) . . ? N10 C27 N9 103.7(4) . . ? N10 C27 Cu1 106.6(3) . . ? N9 C27 Cu1 137.5(4) . . ? N10 C27 Cu3 136.3(4) . . ? N9 C27 Cu3 103.0(3) . . ? Cu1 C27 Cu3 74.08(15) . . ? N2 C1 N1 104.0(4) . . ? N2 C1 Cu1 135.6(4) . . ? N1 C1 Cu1 106.4(3) . . ? N2 C1 Cu2 105.7(3) . . ? N1 C1 Cu2 133.4(4) . . ? Cu1 C1 Cu2 74.83(15) . . ? N5 C14 N6 103.1(4) . . ? N5 C14 Cu3 138.4(4) . . ? N6 C14 Cu3 104.1(3) . . ? N5 C14 Cu2 104.6(3) . . ? N6 C14 Cu2 139.4(4) . . ? Cu3 C14 Cu2 72.70(15) . . ? C9 N4 C13 117.3(5) . . ? C9 N4 Cu2 112.9(4) . . ? C13 N4 Cu2 128.7(3) . . ? C27 N10 C28 111.6(4) . . ? C27 N10 C35 121.8(4) . . ? C28 N10 C35 126.3(4) . . ? C14 N6 C15 111.0(4) . . ? C14 N6 C22 123.3(4) . . ? C15 N6 C22 124.9(4) . . ? C14 N5 C16 111.8(4) . . ? C14 N5 C17 122.2(4) . . ? C16 N5 C17 125.7(4) . . ? C35 N12 C39 117.4(4) . . ? C35 N12 Cu1 112.1(3) . . ? C39 N12 Cu1 130.2(3) . . ? C30 N11 C34 116.3(5) . . ? C30 N11 Cu3 111.9(3) . . ? C34 N11 Cu3 131.1(4) . . ? C1 N1 C3 110.3(5) . . ? C1 N1 C4 121.4(4) . . ? C3 N1 C4 127.7(5) . . ? C27 N9 C29 111.2(4) . . ? C27 N9 C30 121.5(4) . . ? C29 N9 C30 127.2(4) . . ? C1 N2 C2 111.4(5) . . ? C1 N2 C9 121.0(4) . . ? C2 N2 C9 127.1(5) . . ? C4 N3 C8 116.6(5) . . ? C4 N3 Cu1 111.1(4) . . ? C8 N3 Cu1 129.0(3) . . ? C26 N8 C22 117.3(5) . . ? C26 N8 Cu3 130.1(4) . . ? C22 N8 Cu3 111.8(3) . . ? C17 N7 C21 116.6(4) . . ? C17 N7 Cu2 112.5(3) . . ? C21 N7 Cu2 130.2(3) . . ? N12 C35 C36 123.6(5) . . ? N12 C35 N10 113.6(4) . . ? C36 C35 N10 122.8(4) . . ? C15 C16 N5 107.3(4) . . ? C15 C16 H16 126.3 . . ? N5 C16 H16 126.3 . . ? N11 C30 C31 124.3(5) . . ? N11 C30 N9 113.7(4) . . ? C31 C30 N9 121.9(4) . . ? N3 C4 C5 124.5(5) . . ? N3 C4 N1 112.8(5) . . ? C5 C4 N1 122.6(5) . . ? N4 C9 C10 123.7(5) . . ? N4 C9 N2 113.2(4) . . ? C10 C9 N2 123.0(5) . . ? N8 C22 C23 124.0(5) . . ? N8 C22 N6 113.6(4) . . ? C23 C22 N6 122.4(5) . . ? C29 C28 N10 106.4(4) . . ? C29 C28 H28 126.8 . . ? N10 C28 H28 126.8 . . ? C16 C15 N6 106.8(4) . . ? C16 C15 H15 126.6 . . ? N6 C15 H15 126.6 . . ? C28 C29 N9 107.1(4) . . ? C28 C29 H29 126.4 . . ? N9 C29 H29 126.4 . . ? C2 C3 N1 107.5(5) . . ? C2 C3 H3 126.2 . . ? N1 C3 H3 126.2 . . ? N4 C13 C12 122.8(5) . . ? N4 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? N12 C39 C38 123.2(5) . . ? N12 C39 H39 118.4 . . ? C38 C39 H39 118.4 . . ? C30 C31 C32 118.2(5) . . ? C30 C31 H31 120.9 . . ? C32 C31 H31 120.9 . . ? C3 C2 N2 106.7(5) . . ? C3 C2 H2 126.6 . . ? N2 C2 H2 126.6 . . ? N3 C8 C7 123.0(5) . . ? N3 C8 H8 118.5 . . ? C7 C8 H8 118.5 . . ? N7 C17 C18 124.2(5) . . ? N7 C17 N5 114.0(4) . . ? C18 C17 N5 121.8(5) . . ? C37 C36 C35 117.7(5) . . ? C37 C36 H36 121.1 . . ? C35 C36 H36 121.1 . . ? C24 C25 C26 119.6(6) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? N7 C21 C20 123.4(5) . . ? N7 C21 H21 118.3 . . ? C20 C21 H21 118.3 . . ? C25 C24 C23 119.3(6) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C8 C7 C6 118.6(6) . . ? C8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C22 C23 C24 117.6(5) . . ? C22 C23 H23 121.2 . . ? C24 C23 H23 121.2 . . ? N11 C34 C33 124.2(5) . . ? N11 C34 H34 117.9 . . ? C33 C34 H34 117.9 . . ? C12 C11 C10 120.1(6) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N8 C26 C25 122.1(5) . . ? N8 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C34 C33 C32 118.4(5) . . ? C34 C33 H33 120.8 . . ? C32 C33 H33 120.8 . . ? C6 C5 C4 117.2(6) . . ? C6 C5 H5 121.4 . . ? C4 C5 H5 121.4 . . ? C36 C37 C38 120.5(5) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C39 C38 C37 117.5(5) . . ? C39 C38 H38 121.2 . . ? C37 C38 H38 121.2 . . ? C31 C32 C33 118.5(6) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C21 C20 C19 118.3(6) . . ? C21 C20 H20 120.9 . . ? C19 C20 H20 120.9 . . ? C9 C10 C11 117.6(5) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? C19 C18 C17 117.2(5) . . ? C19 C18 H18 121.4 . . ? C17 C18 H18 121.4 . . ? C20 C19 C18 120.2(6) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C11 C12 C13 118.5(6) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? F14 P3 F15 94.1(5) . . ? F14 P3 F13 177.6(5) . . ? F15 P3 F13 88.0(5) . . ? F14 P3 F17 88.3(4) . . ? F15 P3 F17 177.4(5) . . ? F13 P3 F17 89.6(5) . . ? F14 P3 F18 90.5(4) . . ? F15 P3 F18 89.7(3) . . ? F13 P3 F18 90.6(4) . . ? F17 P3 F18 91.2(3) . . ? F14 P3 F16 88.5(4) . . ? F15 P3 F16 91.1(3) . . ? F13 P3 F16 90.4(4) . . ? F17 P3 F16 88.0(3) . . ? F18 P3 F16 178.7(3) . . ? C5 C6 C7 120.2(6) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? 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 C1 Cu1 Cu2 N7 -79.9(2) . . . . ? C27 Cu1 Cu2 N7 99.0(2) . . . . ? N12 Cu1 Cu2 N7 -168.03(17) . . . . ? N3 Cu1 Cu2 N7 -15.32(18) . . . . ? Cu3 Cu1 Cu2 N7 94.73(14) . . . . ? C1 Cu1 Cu2 N4 65.5(2) . . . . ? C27 Cu1 Cu2 N4 -115.66(19) . . . . ? N12 Cu1 Cu2 N4 -22.66(16) . . . . ? N3 Cu1 Cu2 N4 130.04(16) . . . . ? Cu3 Cu1 Cu2 N4 -119.90(12) . . . . ? C27 Cu1 Cu2 C1 178.9(2) . . . . ? N12 Cu1 Cu2 C1 -88.1(2) . . . . ? N3 Cu1 Cu2 C1 64.6(2) . . . . ? Cu3 Cu1 Cu2 C1 174.63(19) . . . . ? C1 Cu1 Cu2 C14 -176.9(2) . . . . ? C27 Cu1 Cu2 C14 2.0(2) . . . . ? N12 Cu1 Cu2 C14 94.97(19) . . . . ? N3 Cu1 Cu2 C14 -112.32(19) . . . . ? Cu3 Cu1 Cu2 C14 -2.27(15) . . . . ? C1 Cu1 Cu2 Cu3 -174.63(19) . . . . ? C27 Cu1 Cu2 Cu3 4.24(15) . . . . ? N12 Cu1 Cu2 Cu3 97.24(12) . . . . ? N3 Cu1 Cu2 Cu3 -110.06(12) . . . . ? N7 Cu2 Cu3 N8 123.87(17) . . . . ? N4 Cu2 Cu3 N8 -27.56(18) . . . . ? C1 Cu2 Cu3 N8 -121.2(2) . . . . ? C14 Cu2 Cu3 N8 60.8(2) . . . . ? Cu1 Cu2 Cu3 N8 -116.61(12) . . . . ? N7 Cu2 Cu3 N11 -30.71(18) . . . . ? N4 Cu2 Cu3 N11 177.86(18) . . . . ? C1 Cu2 Cu3 N11 84.3(2) . . . . ? C14 Cu2 Cu3 N11 -93.8(2) . . . . ? Cu1 Cu2 Cu3 N11 88.81(12) . . . . ? N7 Cu2 Cu3 C14 63.1(2) . . . . ? N4 Cu2 Cu3 C14 -88.4(2) . . . . ? C1 Cu2 Cu3 C14 178.0(2) . . . . ? Cu1 Cu2 Cu3 C14 -177.42(17) . . . . ? N7 Cu2 Cu3 C27 -123.61(19) . . . . ? N4 Cu2 Cu3 C27 85.0(2) . . . . ? C1 Cu2 Cu3 C27 -8.6(2) . . . . ? C14 Cu2 Cu3 C27 173.3(2) . . . . ? Cu1 Cu2 Cu3 C27 -4.09(15) . . . . ? N7 Cu2 Cu3 Cu1 -119.52(13) . . . . ? N4 Cu2 Cu3 Cu1 89.05(13) . . . . ? C1 Cu2 Cu3 Cu1 -4.55(16) . . . . ? C14 Cu2 Cu3 Cu1 177.42(17) . . . . ? C1 Cu1 Cu3 N8 104.7(2) . . . . ? C27 Cu1 Cu3 N8 -75.1(2) . . . . ? N12 Cu1 Cu3 N8 -10.97(17) . . . . ? N3 Cu1 Cu3 N8 -163.04(17) . . . . ? Cu2 Cu1 Cu3 N8 100.07(13) . . . . ? C1 Cu1 Cu3 N11 -112.65(19) . . . . ? C27 Cu1 Cu3 N11 67.5(2) . . . . ? N12 Cu1 Cu3 N11 131.65(16) . . . . ? N3 Cu1 Cu3 N11 -20.42(16) . . . . ? Cu2 Cu1 Cu3 N11 -117.31(11) . . . . ? C1 Cu1 Cu3 C14 6.9(2) . . . . ? C27 Cu1 Cu3 C14 -172.9(2) . . . . ? N12 Cu1 Cu3 C14 -108.76(19) . . . . ? N3 Cu1 Cu3 C14 99.17(19) . . . . ? Cu2 Cu1 Cu3 C14 2.28(15) . . . . ? C1 Cu1 Cu3 C27 179.8(2) . . . . ? N12 Cu1 Cu3 C27 64.1(2) . . . . ? N3 Cu1 Cu3 C27 -87.9(2) . . . . ? Cu2 Cu1 Cu3 C27 175.18(17) . . . . ? C1 Cu1 Cu3 Cu2 4.66(16) . . . . ? C27 Cu1 Cu3 Cu2 -175.18(17) . . . . ? N12 Cu1 Cu3 Cu2 -111.04(12) . . . . ? N3 Cu1 Cu3 Cu2 96.89(12) . . . . ? C1 Cu1 C27 N10 133.8(8) . . . . ? N12 Cu1 C27 N10 13.4(3) . . . . ? N3 Cu1 C27 N10 -112.8(3) . . . . ? Cu3 Cu1 C27 N10 134.4(4) . . . . ? Cu2 Cu1 C27 N10 129.9(3) . . . . ? C1 Cu1 C27 N9 -92.6(10) . . . . ? N12 Cu1 C27 N9 147.0(5) . . . . ? N3 Cu1 C27 N9 20.8(5) . . . . ? Cu3 Cu1 C27 N9 -92.0(5) . . . . ? Cu2 Cu1 C27 N9 -96.5(5) . . . . ? C1 Cu1 C27 Cu3 -0.6(9) . . . . ? N12 Cu1 C27 Cu3 -121.01(16) . . . . ? N3 Cu1 C27 Cu3 112.83(14) . . . . ? Cu2 Cu1 C27 Cu3 -4.50(16) . . . . ? N8 Cu3 C27 N10 27.7(5) . . . . ? N11 Cu3 C27 N10 147.8(5) . . . . ? C14 Cu3 C27 N10 -72.0(9) . . . . ? Cu2 Cu3 C27 N10 -93.0(4) . . . . ? Cu1 Cu3 C27 N10 -97.5(5) . . . . ? N8 Cu3 C27 N9 -98.7(3) . . . . ? N11 Cu3 C27 N9 21.5(3) . . . . ? C14 Cu3 C27 N9 161.6(6) . . . . ? Cu2 Cu3 C27 N9 140.6(3) . . . . ? Cu1 Cu3 C27 N9 136.1(4) . . . . ? N8 Cu3 C27 Cu1 125.23(15) . . . . ? N11 Cu3 C27 Cu1 -114.64(16) . . . . ? C14 Cu3 C27 Cu1 25.5(8) . . . . ? Cu2 Cu3 C27 Cu1 4.52(16) . . . . ? C27 Cu1 C1 N2 -101.5(9) . . . . ? N12 Cu1 C1 N2 16.5(5) . . . . ? N3 Cu1 C1 N2 142.7(5) . . . . ? Cu3 Cu1 C1 N2 -102.0(5) . . . . ? Cu2 Cu1 C1 N2 -97.1(5) . . . . ? C27 Cu1 C1 N1 127.0(8) . . . . ? N12 Cu1 C1 N1 -115.0(3) . . . . ? N3 Cu1 C1 N1 11.2(3) . . . . ? Cu3 Cu1 C1 N1 126.4(3) . . . . ? Cu2 Cu1 C1 N1 131.4(4) . . . . ? C27 Cu1 C1 Cu2 -4.5(9) . . . . ? N12 Cu1 C1 Cu2 113.58(15) . . . . ? N3 Cu1 C1 Cu2 -120.22(16) . . . . ? Cu3 Cu1 C1 Cu2 -4.99(17) . . . . ? N7 Cu2 C1 N2 -102.5(3) . . . . ? N4 Cu2 C1 N2 16.7(3) . . . . ? C14 Cu2 C1 N2 145.2(7) . . . . ? Cu3 Cu2 C1 N2 138.9(3) . . . . ? Cu1 Cu2 C1 N2 133.9(4) . . . . ? N7 Cu2 C1 N1 25.2(5) . . . . ? N4 Cu2 C1 N1 144.4(5) . . . . ? C14 Cu2 C1 N1 -87.2(9) . . . . ? Cu3 Cu2 C1 N1 -93.4(4) . . . . ? Cu1 Cu2 C1 N1 -98.5(5) . . . . ? N7 Cu2 C1 Cu1 123.67(15) . . . . ? N4 Cu2 C1 Cu1 -117.18(17) . . . . ? C14 Cu2 C1 Cu1 11.3(9) . . . . ? Cu3 Cu2 C1 Cu1 5.03(17) . . . . ? N8 Cu3 C14 N5 141.1(5) . . . . ? N11 Cu3 C14 N5 20.6(5) . . . . ? C27 Cu3 C14 N5 -116.9(7) . . . . ? Cu2 Cu3 C14 N5 -92.7(5) . . . . ? Cu1 Cu3 C14 N5 -95.1(5) . . . . ? N8 Cu3 C14 N6 11.7(3) . . . . ? N11 Cu3 C14 N6 -108.8(3) . . . . ? C27 Cu3 C14 N6 113.6(7) . . . . ? Cu2 Cu3 C14 N6 137.9(4) . . . . ? Cu1 Cu3 C14 N6 135.4(3) . . . . ? N8 Cu3 C14 Cu2 -126.25(16) . . . . ? N11 Cu3 C14 Cu2 113.32(14) . . . . ? C27 Cu3 C14 Cu2 -24.3(8) . . . . ? Cu1 Cu3 C14 Cu2 -2.46(16) . . . . ? N7 Cu2 C14 N5 14.5(3) . . . . ? N4 Cu2 C14 N5 -104.8(3) . . . . ? C1 Cu2 C14 N5 129.5(7) . . . . ? Cu3 Cu2 C14 N5 136.8(4) . . . . ? Cu1 Cu2 C14 N5 139.2(3) . . . . ? N7 Cu2 C14 N6 146.1(5) . . . . ? N4 Cu2 C14 N6 26.8(5) . . . . ? C1 Cu2 C14 N6 -98.9(9) . . . . ? Cu3 Cu2 C14 N6 -91.7(5) . . . . ? Cu1 Cu2 C14 N6 -89.2(5) . . . . ? N7 Cu2 C14 Cu3 -122.22(16) . . . . ? N4 Cu2 C14 Cu3 118.44(14) . . . . ? C1 Cu2 C14 Cu3 -7.2(8) . . . . ? Cu1 Cu2 C14 Cu3 2.45(16) . . . . ? N7 Cu2 N4 C9 95.7(3) . . . . ? C1 Cu2 N4 C9 -5.3(3) . . . . ? C14 Cu2 N4 C9 -173.3(3) . . . . ? Cu3 Cu2 N4 C9 -115.7(3) . . . . ? Cu1 Cu2 N4 C9 -51.6(3) . . . . ? N7 Cu2 N4 C13 -96.7(4) . . . . ? C1 Cu2 N4 C13 162.3(4) . . . . ? C14 Cu2 N4 C13 -5.7(5) . . . . ? Cu3 Cu2 N4 C13 51.9(5) . . . . ? Cu1 Cu2 N4 C13 115.9(4) . . . . ? N9 C27 N10 C28 1.5(5) . . . . ? Cu1 C27 N10 C28 151.2(3) . . . . ? Cu3 C27 N10 C28 -124.6(5) . . . . ? N9 C27 N10 C35 -172.2(4) . . . . ? Cu1 C27 N10 C35 -22.4(5) . . . . ? Cu3 C27 N10 C35 61.7(6) . . . . ? N5 C14 N6 C15 -0.3(5) . . . . ? Cu3 C14 N6 C15 148.0(3) . . . . ? Cu2 C14 N6 C15 -132.2(5) . . . . ? N5 C14 N6 C22 -171.2(4) . . . . ? Cu3 C14 N6 C22 -22.9(5) . . . . ? Cu2 C14 N6 C22 56.8(7) . . . . ? N6 C14 N5 C16 0.1(5) . . . . ? Cu3 C14 N5 C16 -129.7(5) . . . . ? Cu2 C14 N5 C16 150.1(3) . . . . ? N6 C14 N5 C17 -174.6(4) . . . . ? Cu3 C14 N5 C17 55.7(7) . . . . ? Cu2 C14 N5 C17 -24.5(5) . . . . ? C1 Cu1 N12 C35 -172.3(3) . . . . ? C27 Cu1 N12 C35 -4.4(3) . . . . ? N3 Cu1 N12 C35 96.6(4) . . . . ? Cu3 Cu1 N12 C35 -51.7(3) . . . . ? Cu2 Cu1 N12 C35 -116.3(3) . . . . ? C1 Cu1 N12 C39 0.7(5) . . . . ? C27 Cu1 N12 C39 168.6(5) . . . . ? N3 Cu1 N12 C39 -90.4(5) . . . . ? Cu3 Cu1 N12 C39 121.3(4) . . . . ? Cu2 Cu1 N12 C39 56.7(5) . . . . ? N8 Cu3 N11 C30 86.4(3) . . . . ? C14 Cu3 N11 C30 -179.9(3) . . . . ? C27 Cu3 N11 C30 -10.2(3) . . . . ? Cu2 Cu3 N11 C30 -121.0(3) . . . . ? Cu1 Cu3 N11 C30 -57.5(3) . . . . ? N8 Cu3 N11 C34 -104.0(4) . . . . ? C14 Cu3 N11 C34 -10.3(5) . . . . ? C27 Cu3 N11 C34 159.4(5) . . . . ? Cu2 Cu3 N11 C34 48.7(5) . . . . ? Cu1 Cu3 N11 C34 112.1(4) . . . . ? N2 C1 N1 C3 -0.5(5) . . . . ? Cu1 C1 N1 C3 146.8(3) . . . . ? Cu2 C1 N1 C3 -128.7(4) . . . . ? N2 C1 N1 C4 -172.7(4) . . . . ? Cu1 C1 N1 C4 -25.4(5) . . . . ? Cu2 C1 N1 C4 59.0(6) . . . . ? N10 C27 N9 C29 -1.3(5) . . . . ? Cu1 C27 N9 C29 -135.7(4) . . . . ? Cu3 C27 N9 C29 143.8(3) . . . . ? N10 C27 N9 C30 -178.1(4) . . . . ? Cu1 C27 N9 C30 47.5(7) . . . . ? Cu3 C27 N9 C30 -33.0(5) . . . . ? N1 C1 N2 C2 0.8(5) . . . . ? Cu1 C1 N2 C2 -131.5(4) . . . . ? Cu2 C1 N2 C2 144.4(3) . . . . ? N1 C1 N2 C9 -171.7(4) . . . . ? Cu1 C1 N2 C9 56.0(6) . . . . ? Cu2 C1 N2 C9 -28.1(5) . . . . ? C1 Cu1 N3 C4 2.6(3) . . . . ? C27 Cu1 N3 C4 -164.9(3) . . . . ? N12 Cu1 N3 C4 105.0(3) . . . . ? Cu3 Cu1 N3 C4 -108.6(3) . . . . ? Cu2 Cu1 N3 C4 -44.4(3) . . . . ? C1 Cu1 N3 C8 161.0(5) . . . . ? C27 Cu1 N3 C8 -6.5(5) . . . . ? N12 Cu1 N3 C8 -96.6(4) . . . . ? Cu3 Cu1 N3 C8 49.8(5) . . . . ? Cu2 Cu1 N3 C8 114.0(4) . . . . ? N11 Cu3 N8 C26 -82.8(5) . . . . ? C14 Cu3 N8 C26 168.1(5) . . . . ? C27 Cu3 N8 C26 3.1(5) . . . . ? Cu2 Cu3 N8 C26 122.9(5) . . . . ? Cu1 Cu3 N8 C26 53.7(5) . . . . ? N11 Cu3 N8 C22 108.0(3) . . . . ? C14 Cu3 N8 C22 -1.2(3) . . . . ? C27 Cu3 N8 C22 -166.1(3) . . . . ? Cu2 Cu3 N8 C22 -46.4(4) . . . . ? Cu1 Cu3 N8 C22 -115.6(3) . . . . ? N4 Cu2 N7 C17 101.3(4) . . . . ? C1 Cu2 N7 C17 -171.1(3) . . . . ? C14 Cu2 N7 C17 -4.7(3) . . . . ? Cu3 Cu2 N7 C17 -51.1(4) . . . . ? Cu1 Cu2 N7 C17 -118.2(3) . . . . ? N4 Cu2 N7 C21 -88.7(5) . . . . ? C1 Cu2 N7 C21 -1.0(5) . . . . ? C14 Cu2 N7 C21 165.3(5) . . . . ? Cu3 Cu2 N7 C21 119.0(4) . . . . ? Cu1 Cu2 N7 C21 51.9(5) . . . . ? C39 N12 C35 C36 -0.6(7) . . . . ? Cu1 N12 C35 C36 173.4(4) . . . . ? C39 N12 C35 N10 -179.7(4) . . . . ? Cu1 N12 C35 N10 -5.8(5) . . . . ? C27 N10 C35 N12 20.1(6) . . . . ? C28 N10 C35 N12 -152.6(5) . . . . ? C27 N10 C35 C36 -159.1(5) . . . . ? C28 N10 C35 C36 28.3(8) . . . . ? C14 N5 C16 C15 0.2(6) . . . . ? C17 N5 C16 C15 174.6(5) . . . . ? C34 N11 C30 C31 2.4(7) . . . . ? Cu3 N11 C30 C31 173.7(4) . . . . ? C34 N11 C30 N9 -175.2(4) . . . . ? Cu3 N11 C30 N9 -3.9(5) . . . . ? C27 N9 C30 N11 27.2(6) . . . . ? C29 N9 C30 N11 -149.1(5) . . . . ? C27 N9 C30 C31 -150.5(5) . . . . ? C29 N9 C30 C31 33.3(7) . . . . ? C8 N3 C4 C5 0.0(7) . . . . ? Cu1 N3 C4 C5 161.3(4) . . . . ? C8 N3 C4 N1 -177.1(4) . . . . ? Cu1 N3 C4 N1 -15.8(5) . . . . ? C1 N1 C4 N3 29.3(6) . . . . ? C3 N1 C4 N3 -141.4(5) . . . . ? C1 N1 C4 C5 -147.9(5) . . . . ? C3 N1 C4 C5 41.4(7) . . . . ? C13 N4 C9 C10 1.2(7) . . . . ? Cu2 N4 C9 C10 170.4(4) . . . . ? C13 N4 C9 N2 -176.6(4) . . . . ? Cu2 N4 C9 N2 -7.5(5) . . . . ? C1 N2 C9 N4 25.5(6) . . . . ? C2 N2 C9 N4 -145.7(4) . . . . ? C1 N2 C9 C10 -152.4(5) . . . . ? C2 N2 C9 C10 36.4(7) . . . . ? C26 N8 C22 C23 1.2(7) . . . . ? Cu3 N8 C22 C23 172.0(4) . . . . ? C26 N8 C22 N6 179.2(4) . . . . ? Cu3 N8 C22 N6 -10.0(5) . . . . ? C14 N6 C22 N8 23.9(6) . . . . ? C15 N6 C22 N8 -145.7(5) . . . . ? C14 N6 C22 C23 -158.0(5) . . . . ? C15 N6 C22 C23 32.3(7) . . . . ? C27 N10 C28 C29 -1.1(6) . . . . ? C35 N10 C28 C29 172.2(5) . . . . ? N5 C16 C15 N6 -0.3(6) . . . . ? C14 N6 C15 C16 0.4(6) . . . . ? C22 N6 C15 C16 171.1(5) . . . . ? N10 C28 C29 N9 0.3(6) . . . . ? C27 N9 C29 C28 0.7(6) . . . . ? C30 N9 C29 C28 177.2(5) . . . . ? C1 N1 C3 C2 0.1(6) . . . . ? C4 N1 C3 C2 171.7(5) . . . . ? C9 N4 C13 C12 -0.9(7) . . . . ? Cu2 N4 C13 C12 -168.0(4) . . . . ? C35 N12 C39 C38 0.3(8) . . . . ? Cu1 N12 C39 C38 -172.3(4) . . . . ? N11 C30 C31 C32 -2.4(8) . . . . ? N9 C30 C31 C32 175.0(5) . . . . ? N1 C3 C2 N2 0.4(6) . . . . ? C1 N2 C2 C3 -0.8(6) . . . . ? C9 N2 C2 C3 171.2(5) . . . . ? C4 N3 C8 C7 1.3(7) . . . . ? Cu1 N3 C8 C7 -156.1(4) . . . . ? C21 N7 C17 C18 1.1(8) . . . . ? Cu2 N7 C17 C18 172.6(4) . . . . ? C21 N7 C17 N5 -178.0(4) . . . . ? Cu2 N7 C17 N5 -6.5(5) . . . . ? C14 N5 C17 N7 22.6(6) . . . . ? C16 N5 C17 N7 -151.3(5) . . . . ? C14 N5 C17 C18 -156.5(5) . . . . ? C16 N5 C17 C18 29.6(8) . . . . ? N12 C35 C36 C37 1.4(8) . . . . ? N10 C35 C36 C37 -179.5(5) . . . . ? C17 N7 C21 C20 -2.4(8) . . . . ? Cu2 N7 C21 C20 -172.2(5) . . . . ? C26 C25 C24 C23 0.3(10) . . . . ? N3 C8 C7 C6 -1.9(9) . . . . ? N8 C22 C23 C24 -1.6(8) . . . . ? N6 C22 C23 C24 -179.4(5) . . . . ? C25 C24 C23 C22 0.7(9) . . . . ? C30 N11 C34 C33 -2.0(8) . . . . ? Cu3 N11 C34 C33 -171.3(4) . . . . ? C22 N8 C26 C25 -0.1(8) . . . . ? Cu3 N8 C26 C25 -168.8(5) . . . . ? C24 C25 C26 N8 -0.7(10) . . . . ? N11 C34 C33 C32 1.7(9) . . . . ? N3 C4 C5 C6 -0.5(8) . . . . ? N1 C4 C5 C6 176.3(5) . . . . ? C35 C36 C37 C38 -1.9(9) . . . . ? N12 C39 C38 C37 -0.9(8) . . . . ? C36 C37 C38 C39 1.7(9) . . . . ? C30 C31 C32 C33 1.9(8) . . . . ? C34 C33 C32 C31 -1.5(8) . . . . ? N7 C21 C20 C19 1.6(9) . . . . ? N4 C9 C10 C11 -1.8(8) . . . . ? N2 C9 C10 C11 175.9(5) . . . . ? C12 C11 C10 C9 1.8(9) . . . . ? N7 C17 C18 C19 1.0(9) . . . . ? N5 C17 C18 C19 180.0(5) . . . . ? C21 C20 C19 C18 0.6(10) . . . . ? C17 C18 C19 C20 -1.8(9) . . . . ? C10 C11 C12 C13 -1.5(9) . . . . ? N4 C13 C12 C11 1.0(8) . . . . ? C4 C5 C6 C7 -0.2(9) . . . . ? C8 C7 C6 C5 1.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.541 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.080 #===END data_090115e _database_code_depnum_ccdc_archive 'CCDC 782458' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 F12 Fe N10 P2' _chemical_formula_weight 748.27 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M '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 14.1189(14) _cell_length_b 17.770(2) _cell_length_c 12.6099(13) _cell_angle_alpha 90.00 _cell_angle_beta 105.422(2) _cell_angle_gamma 90.00 _cell_volume 3049.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7708 _exptl_absorpt_correction_T_max 0.8327 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 15160 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5360 _reflns_number_gt 3317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SMART' _computing_publication_material 'Bruker SMART' _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^)+(0.0990P)^2^+8.4095P] 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 5360 _refine_ls_number_parameters 502 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2239 _refine_ls_wR_factor_gt 0.1834 _refine_ls_goodness_of_fit_ref 1.023 _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 Fe1 Fe 0.24584(5) 0.49867(4) 0.24848(6) 0.0403(3) Uani 1 1 d . . . F1 F 0.1465(5) 0.2305(3) 0.5691(6) 0.151(2) Uani 1 1 d . A . F2 F 0.1485(7) 0.3990(4) 0.6352(6) 0.192(4) Uani 1 1 d . A . F3 F 0.0544(9) 0.3333(8) 0.5020(16) 0.122(6) Uani 0.65(4) 1 d P A 1 F4 F 0.2029(13) 0.3504(14) 0.5129(17) 0.149(7) Uani 0.65(4) 1 d P A 1 F5 F 0.2498(10) 0.3162(10) 0.6838(13) 0.136(6) Uani 0.65(4) 1 d P A 1 F6 F 0.0937(19) 0.2997(9) 0.681(2) 0.167(9) Uani 0.65(4) 1 d P A 1 F7 F 0.3084(12) 0.6389(10) 0.8154(13) 0.158(7) Uani 0.65(2) 1 d P B 1 F8 F 0.4858(14) 0.6367(14) 0.999(2) 0.179(10) Uani 0.65(2) 1 d P B 1 F9 F 0.4252(16) 0.5569(9) 0.8740(17) 0.189(8) Uani 0.65(2) 1 d P B 1 F10 F 0.3331(8) 0.6045(8) 0.9787(9) 0.129(6) Uani 0.65(2) 1 d P B 1 F11 F 0.3772(15) 0.7222(7) 0.9376(11) 0.143(6) Uani 0.65(2) 1 d P B 1 F12 F 0.4564(15) 0.6723(13) 0.8233(18) 0.192(8) Uani 0.65(2) 1 d P B 1 F3' F 0.0399(18) 0.307(2) 0.573(4) 0.154(14) Uani 0.35(4) 1 d P A 2 F4' F 0.175(4) 0.312(3) 0.489(3) 0.164(13) Uani 0.35(4) 1 d P A 2 F5' F 0.2655(18) 0.2889(19) 0.623(4) 0.150(13) Uani 0.35(4) 1 d P A 2 F6' F 0.165(3) 0.2838(12) 0.7279(16) 0.121(11) Uani 0.35(4) 1 d P A 2 F7' F 0.382(3) 0.6364(17) 0.7884(15) 0.147(12) Uani 0.35(2) 1 d P B 2 F8' F 0.437(3) 0.650(3) 1.022(3) 0.159(15) Uani 0.35(2) 1 d P B 2 F9' F 0.512(2) 0.609(2) 0.909(3) 0.172(14) Uani 0.35(2) 1 d P B 2 F10' F 0.367(2) 0.5567(16) 0.916(3) 0.163(12) Uani 0.35(2) 1 d P B 2 F11' F 0.2962(19) 0.6720(17) 0.900(3) 0.164(13) Uani 0.35(2) 1 d P B 2 F12' F 0.438(2) 0.7269(14) 0.895(3) 0.147(11) Uani 0.35(2) 1 d P B 2 N1 N 0.0748(4) 0.5736(3) 0.1444(4) 0.0666(15) Uani 1 1 d . . . N2 N 0.1858(5) 0.6575(3) 0.1543(5) 0.0697(15) Uani 1 1 d . . . N3 N 0.1116(3) 0.4563(3) 0.2150(4) 0.0499(11) Uani 1 1 d . . . N4 N -0.0551(4) 0.4898(5) 0.1267(6) 0.093(2) Uani 1 1 d . . . N5 N 0.3410(4) 0.5650(3) 0.4478(4) 0.0589(13) Uani 1 1 d . . . N6 N 0.1974(4) 0.5473(3) 0.4640(4) 0.0632(14) Uani 1 1 d . . . N7 N 0.3817(3) 0.5399(3) 0.2877(4) 0.0480(11) Uani 1 1 d . . . N8 N 0.5016(4) 0.5909(3) 0.4442(5) 0.0746(16) Uani 1 1 d . . . N9 N 0.3059(3) 0.4017(3) 0.3085(4) 0.0520(12) Uani 1 1 d . . . N10 N 0.2565(3) 0.4615(3) 0.1045(4) 0.0497(11) Uani 1 1 d . . . P1 P 0.15153(17) 0.31506(13) 0.5976(2) 0.0882(7) Uani 1 1 d . . . P2 P 0.4016(2) 0.63980(14) 0.90495(19) 0.0902(7) Uani 1 1 d . . . C1 C 0.1749(4) 0.5854(3) 0.1818(5) 0.0537(14) Uani 1 1 d . . . C2 C 0.0949(7) 0.6889(5) 0.1020(7) 0.091(3) Uani 1 1 d . . . H2 H 0.0851 0.7380 0.0761 0.109 Uiso 1 1 calc R . . C3 C 0.0251(7) 0.6388(5) 0.0945(7) 0.094(3) Uani 1 1 d . . . H3 H -0.0420 0.6449 0.0633 0.113 Uiso 1 1 calc R . . C4 C 0.0389(4) 0.5026(4) 0.1606(5) 0.0632(16) Uani 1 1 d . . . C5 C -0.0819(6) 0.4215(6) 0.1481(8) 0.098(3) Uani 1 1 d . . . H5 H -0.1481 0.4090 0.1247 0.117 Uiso 1 1 calc R . . C6 C -0.0172(5) 0.3681(5) 0.2029(7) 0.090(2) Uani 1 1 d . . . H6 H -0.0381 0.3205 0.2176 0.108 Uiso 1 1 calc R . . C7 C 0.0809(5) 0.3884(4) 0.2352(6) 0.0680(17) Uani 1 1 d . . . H7 H 0.1268 0.3534 0.2723 0.082 Uiso 1 1 calc R . . C8 C 0.2789(7) 0.6973(4) 0.1765(7) 0.099(3) Uani 1 1 d . . . H8A H 0.3095 0.6970 0.2542 0.149 Uiso 1 1 calc R . . H8B H 0.2676 0.7483 0.1512 0.149 Uiso 1 1 calc R . . H8C H 0.3210 0.6728 0.1387 0.149 Uiso 1 1 calc R . . C9 C 0.2506(4) 0.5361(3) 0.3917(4) 0.0437(12) Uani 1 1 d . . . C10 C 0.2527(6) 0.5804(4) 0.5601(6) 0.075(2) Uani 1 1 d . . . H10 H 0.2305 0.5928 0.6210 0.090 Uiso 1 1 calc R . . C11 C 0.3413(6) 0.5912(4) 0.5505(5) 0.077(2) Uani 1 1 d . . . H11 H 0.3940 0.6123 0.6025 0.092 Uiso 1 1 calc R . . C12 C 0.4140(4) 0.5662(3) 0.3922(5) 0.0563(15) Uani 1 1 d . . . C13 C 0.5657(6) 0.5908(5) 0.3838(7) 0.091(2) Uani 1 1 d . . . H13 H 0.6291 0.6080 0.4155 0.109 Uiso 1 1 calc R . . C14 C 0.5426(5) 0.5663(5) 0.2771(7) 0.085(2) Uani 1 1 d . . . H14 H 0.5888 0.5674 0.2365 0.102 Uiso 1 1 calc R . . C15 C 0.4498(5) 0.5403(4) 0.2321(5) 0.0668(17) Uani 1 1 d . . . H15 H 0.4335 0.5221 0.1603 0.080 Uiso 1 1 calc R . . C16 C 0.0934(5) 0.5286(5) 0.4452(7) 0.080(2) Uani 1 1 d . . . H16A H 0.0559 0.5542 0.3805 0.120 Uiso 1 1 calc R . . H16B H 0.0713 0.5440 0.5075 0.120 Uiso 1 1 calc R . . H16C H 0.0848 0.4752 0.4351 0.120 Uiso 1 1 calc R . . C17 C 0.3468(5) 0.3481(4) 0.3309(6) 0.0717(19) Uani 1 1 d . . . C18 C 0.4013(7) 0.2773(4) 0.3644(10) 0.141(5) Uani 1 1 d . . . H18A H 0.4535 0.2859 0.4297 0.211 Uiso 1 1 calc R . . H18B H 0.4283 0.2602 0.3064 0.211 Uiso 1 1 calc R . . H18C H 0.3574 0.2398 0.3790 0.211 Uiso 1 1 calc R . . C19 C 0.2612(4) 0.4377(4) 0.0233(5) 0.0600(16) Uani 1 1 d . . . C20 C 0.2691(6) 0.4047(6) -0.0782(7) 0.103(3) Uani 1 1 d . . . H20A H 0.3335 0.3835 -0.0678 0.155 Uiso 1 1 calc R . . H20B H 0.2584 0.4427 -0.1342 0.155 Uiso 1 1 calc R . . H20C H 0.2207 0.3658 -0.1001 0.155 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 Fe1 0.0356(4) 0.0460(4) 0.0362(4) -0.0013(3) 0.0041(3) 0.0006(3) F1 0.172(6) 0.103(4) 0.160(6) -0.031(4) 0.013(5) -0.007(4) F2 0.255(9) 0.107(5) 0.164(7) -0.027(4) -0.034(6) -0.011(5) F3 0.097(7) 0.124(9) 0.116(11) -0.008(7) -0.021(7) 0.004(6) F4 0.137(10) 0.194(18) 0.119(11) 0.014(11) 0.039(8) -0.069(10) F5 0.105(8) 0.180(12) 0.097(9) -0.025(8) -0.020(6) 0.005(8) F6 0.18(2) 0.187(13) 0.153(18) -0.004(11) 0.073(17) -0.028(12) F7 0.136(11) 0.201(14) 0.118(11) 0.007(10) 0.001(9) -0.053(10) F8 0.112(14) 0.187(17) 0.19(2) 0.006(18) -0.050(13) -0.003(13) F9 0.20(2) 0.139(13) 0.236(19) -0.051(12) 0.075(14) 0.023(13) F10 0.124(8) 0.159(12) 0.113(8) 0.012(7) 0.045(6) -0.038(7) F11 0.188(16) 0.107(9) 0.135(10) -0.025(7) 0.042(10) 0.000(9) F12 0.192(18) 0.220(19) 0.200(17) 0.012(15) 0.112(15) -0.048(14) F3' 0.115(16) 0.16(2) 0.15(3) -0.02(2) -0.020(18) -0.007(14) F4' 0.19(4) 0.18(3) 0.113(19) -0.005(19) 0.03(2) -0.04(2) F5' 0.127(17) 0.16(2) 0.16(3) -0.005(19) 0.021(17) -0.026(14) F6' 0.15(2) 0.097(13) 0.084(11) -0.002(8) -0.016(13) -0.028(13) F7' 0.18(3) 0.19(3) 0.078(12) -0.039(13) 0.047(16) -0.01(2) F8' 0.18(4) 0.18(3) 0.13(2) -0.012(19) 0.07(3) -0.02(3) F9' 0.14(2) 0.19(3) 0.18(3) -0.02(2) 0.04(2) 0.05(2) F10' 0.18(3) 0.14(2) 0.18(3) 0.00(2) 0.07(2) -0.03(2) F11' 0.14(2) 0.17(3) 0.18(3) -0.02(2) 0.06(2) 0.005(18) F12' 0.15(2) 0.132(18) 0.15(2) -0.009(16) 0.036(17) -0.035(16) N1 0.051(3) 0.077(4) 0.063(3) 0.009(3) 0.000(3) 0.022(3) N2 0.094(4) 0.049(3) 0.065(4) 0.006(3) 0.021(3) 0.008(3) N3 0.041(3) 0.059(3) 0.046(3) -0.005(2) 0.005(2) -0.002(2) N4 0.038(3) 0.128(6) 0.099(5) -0.005(4) -0.006(3) 0.001(3) N5 0.054(3) 0.077(3) 0.043(3) -0.011(2) 0.008(2) -0.008(2) N6 0.060(3) 0.074(4) 0.060(3) -0.005(3) 0.025(3) 0.002(3) N7 0.045(3) 0.054(3) 0.045(3) -0.002(2) 0.013(2) -0.006(2) N8 0.056(3) 0.095(4) 0.069(4) -0.010(3) 0.009(3) -0.030(3) N9 0.044(3) 0.057(3) 0.049(3) 0.006(2) 0.000(2) 0.003(2) N10 0.047(3) 0.055(3) 0.044(3) -0.004(2) 0.006(2) 0.002(2) P1 0.0792(15) 0.0836(15) 0.0897(17) 0.0024(12) 0.0015(12) -0.0197(11) P2 0.1099(19) 0.0869(16) 0.0663(14) -0.0068(11) 0.0102(13) -0.0045(13) C1 0.061(4) 0.059(4) 0.040(3) 0.000(3) 0.010(3) 0.012(3) C2 0.108(7) 0.074(5) 0.088(6) 0.022(4) 0.020(5) 0.037(5) C3 0.085(6) 0.106(7) 0.081(6) 0.014(5) 0.004(5) 0.041(5) C4 0.042(3) 0.085(5) 0.056(4) -0.002(3) 0.001(3) 0.006(3) C5 0.042(4) 0.131(8) 0.114(7) -0.020(6) 0.011(4) -0.016(5) C6 0.059(5) 0.104(6) 0.106(6) -0.017(5) 0.020(4) -0.031(4) C7 0.050(4) 0.076(5) 0.073(4) -0.004(4) 0.008(3) -0.005(3) C8 0.131(8) 0.060(5) 0.104(7) -0.001(4) 0.026(6) -0.016(5) C9 0.040(3) 0.048(3) 0.043(3) 0.003(2) 0.011(2) 0.000(2) C10 0.084(5) 0.092(5) 0.052(4) -0.018(4) 0.024(4) -0.004(4) C11 0.078(5) 0.102(6) 0.048(4) -0.023(4) 0.011(3) -0.016(4) C12 0.047(3) 0.063(4) 0.056(4) -0.003(3) 0.008(3) -0.009(3) C13 0.059(5) 0.109(6) 0.099(6) -0.004(5) 0.010(4) -0.032(4) C14 0.061(4) 0.119(7) 0.083(5) -0.009(5) 0.032(4) -0.023(4) C15 0.056(4) 0.091(5) 0.057(4) -0.001(4) 0.020(3) -0.014(3) C16 0.059(4) 0.098(5) 0.093(5) -0.004(4) 0.037(4) 0.000(4) C17 0.065(4) 0.051(4) 0.077(5) -0.001(3) -0.019(3) 0.002(3) C18 0.128(8) 0.057(5) 0.181(11) -0.003(6) -0.057(7) 0.021(5) C19 0.050(4) 0.074(4) 0.054(4) -0.015(3) 0.010(3) -0.001(3) C20 0.080(5) 0.153(8) 0.074(5) -0.050(5) 0.014(4) 0.009(5) _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 Fe1 C1 1.908(6) . ? Fe1 C9 1.909(5) . ? Fe1 N10 1.976(5) . ? Fe1 N3 1.978(5) . ? Fe1 N9 1.979(5) . ? Fe1 N7 1.989(4) . ? F1 P1 1.543(6) . ? F2 P1 1.569(7) . ? F3 P1 1.600(13) . ? F4 P1 1.572(16) . ? F5 P1 1.518(11) . ? F6 P1 1.513(13) . ? F7 P2 1.488(11) . ? F8 P2 1.442(16) . ? F9 P2 1.582(14) . ? F10 P2 1.635(10) . ? F11 P2 1.583(11) . ? F12 P2 1.555(12) . ? F3' P1 1.53(3) . ? F4' P1 1.50(4) . ? F5' P1 1.62(3) . ? F6' P1 1.70(2) . ? F7' P2 1.422(18) . ? F8' P2 1.43(4) . ? F9' P2 1.64(2) . ? F10' P2 1.57(3) . ? F11' P2 1.58(2) . ? F12' P2 1.64(2) . ? N1 C1 1.382(8) . ? N1 C4 1.395(8) . ? N1 C3 1.414(9) . ? N2 C1 1.347(8) . ? N2 C2 1.394(10) . ? N2 C8 1.452(10) . ? N3 C7 1.329(8) . ? N3 C4 1.351(8) . ? N4 C4 1.301(8) . ? N4 C5 1.321(11) . ? N5 C11 1.375(8) . ? N5 C9 1.383(7) . ? N5 C12 1.392(7) . ? N6 C9 1.342(7) . ? N6 C10 1.385(8) . ? N6 C16 1.461(8) . ? N7 C15 1.332(7) . ? N7 C12 1.358(7) . ? N8 C12 1.312(7) . ? N8 C13 1.329(9) . ? N9 C17 1.111(7) . ? N10 C19 1.126(7) . ? C2 C3 1.312(12) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C5 C6 1.370(12) . ? C5 H5 0.9300 . ? C6 C7 1.383(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.302(9) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C14 1.369(11) . ? C13 H13 0.9300 . ? C14 C15 1.363(9) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.477(10) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.438(9) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Fe1 C9 91.0(2) . . ? C1 Fe1 N10 91.4(2) . . ? C9 Fe1 N10 173.8(2) . . ? C1 Fe1 N3 81.5(2) . . ? C9 Fe1 N3 97.2(2) . . ? N10 Fe1 N3 88.78(19) . . ? C1 Fe1 N9 173.3(2) . . ? C9 Fe1 N9 92.2(2) . . ? N10 Fe1 N9 86.0(2) . . ? N3 Fe1 N9 92.2(2) . . ? C1 Fe1 N7 99.8(2) . . ? C9 Fe1 N7 81.2(2) . . ? N10 Fe1 N7 92.75(18) . . ? N3 Fe1 N7 177.94(19) . . ? N9 Fe1 N7 86.50(19) . . ? C1 N1 C4 117.8(5) . . ? C1 N1 C3 111.6(7) . . ? C4 N1 C3 130.6(6) . . ? C1 N2 C2 110.4(7) . . ? C1 N2 C8 124.9(6) . . ? C2 N2 C8 124.7(7) . . ? C7 N3 C4 114.0(5) . . ? C7 N3 Fe1 130.3(4) . . ? C4 N3 Fe1 115.6(4) . . ? C4 N4 C5 114.5(7) . . ? C11 N5 C9 112.2(5) . . ? C11 N5 C12 130.6(5) . . ? C9 N5 C12 117.1(5) . . ? C9 N6 C10 111.7(5) . . ? C9 N6 C16 125.1(5) . . ? C10 N6 C16 123.2(6) . . ? C15 N7 C12 114.0(5) . . ? C15 N7 Fe1 130.9(4) . . ? C12 N7 Fe1 114.9(4) . . ? C12 N8 C13 114.1(6) . . ? C17 N9 Fe1 169.9(6) . . ? C19 N10 Fe1 177.4(5) . . ? F4' P1 F6 156.7(16) . . ? F4' P1 F5 105.9(17) . . ? F6 P1 F5 93.8(9) . . ? F4' P1 F3' 106.3(18) . . ? F6 P1 F3' 53.5(13) . . ? F5 P1 F3' 147.3(16) . . ? F4' P1 F1 75.9(18) . . ? F6 P1 F1 89.2(6) . . ? F5 P1 F1 99.0(8) . . ? F3' P1 F1 83.3(11) . . ? F4' P1 F2 110.2(18) . . ? F6 P1 F2 84.2(7) . . ? F5 P1 F2 82.2(8) . . ? F3' P1 F2 92.2(11) . . ? F1 P1 F2 173.3(5) . . ? F4' P1 F4 30.5(13) . . ? F6 P1 F4 166.6(14) . . ? F5 P1 F4 89.0(9) . . ? F3' P1 F4 123(2) . . ? F1 P1 F4 103.4(11) . . ? F2 P1 F4 83.2(11) . . ? F4' P1 F3 70.8(17) . . ? F6 P1 F3 92.6(9) . . ? F5 P1 F3 166.8(10) . . ? F3' P1 F3 40.2(14) . . ? F1 P1 F3 92.6(5) . . ? F2 P1 F3 87.0(5) . . ? F4 P1 F3 82.3(10) . . ? F4' P1 F5' 74(2) . . ? F6 P1 F5' 120.2(12) . . ? F5 P1 F5' 36.4(12) . . ? F3' P1 F5' 158(2) . . ? F1 P1 F5' 75.4(13) . . ? F2 P1 F5' 108.6(15) . . ? F4 P1 F5' 68.5(15) . . ? F3 P1 F5' 144.2(14) . . ? F4' P1 F6' 152(2) . . ? F6 P1 F6' 38.3(8) . . ? F5 P1 F6' 57.6(10) . . ? F3' P1 F6' 90.6(16) . . ? F1 P1 F6' 83.8(7) . . ? F2 P1 F6' 91.4(8) . . ? F4 P1 F6' 146.5(13) . . ? F3 P1 F6' 130.6(11) . . ? F5' P1 F6' 82.3(13) . . ? F7' P2 F8' 170(2) . . ? F7' P2 F8 138(2) . . ? F8' P2 F8 34.3(12) . . ? F7' P2 F7 47.4(12) . . ? F8' P2 F7 140.7(17) . . ? F8 P2 F7 173.6(13) . . ? F7' P2 F12 47.8(13) . . ? F8' P2 F12 123(2) . . ? F8 P2 F12 96.6(15) . . ? F7 P2 F12 89.8(9) . . ? F7' P2 F10' 93.9(19) . . ? F8' P2 F10' 93(2) . . ? F8 P2 F10' 95.6(16) . . ? F7 P2 F10' 79.9(12) . . ? F12 P2 F10' 128.6(16) . . ? F7' P2 F11' 92.7(16) . . ? F8' P2 F11' 93(2) . . ? F8 P2 F11' 127.4(19) . . ? F7 P2 F11' 48.7(11) . . ? F12 P2 F11' 117.9(14) . . ? F10' P2 F11' 92.1(17) . . ? F7' P2 F9 72.7(12) . . ? F8' P2 F9 109(2) . . ? F8 P2 F9 89.3(12) . . ? F7 P2 F9 90.2(11) . . ? F12 P2 F9 90.5(12) . . ? F10' P2 F9 40.0(10) . . ? F11' P2 F9 125.8(15) . . ? F7' P2 F11 108.1(12) . . ? F8' P2 F11 70(2) . . ? F8 P2 F11 90.5(12) . . ? F7 P2 F11 89.9(9) . . ? F12 P2 F11 90.6(9) . . ? F10' P2 F11 139.0(16) . . ? F11' P2 F11 53.7(10) . . ? F9 P2 F11 178.9(11) . . ? F7' P2 F10 125.9(18) . . ? F8' P2 F10 63.7(16) . . ? F8 P2 F10 89.9(12) . . ? F7 P2 F10 83.7(8) . . ? F12 P2 F10 173.4(10) . . ? F10' P2 F10 49.4(12) . . ? F11' P2 F10 57.9(11) . . ? F9 P2 F10 88.7(10) . . ? F11 P2 F10 90.3(10) . . ? F7' P2 F9' 86.8(19) . . ? F8' P2 F9' 86.8(16) . . ? F8 P2 F9' 52.6(12) . . ? F7 P2 F9' 131.4(16) . . ? F12 P2 F9' 60.5(12) . . ? F10' P2 F9' 89.7(17) . . ? F11' P2 F9' 178.1(18) . . ? F9 P2 F9' 55.8(12) . . ? F11 P2 F9' 124.7(17) . . ? F10 P2 F9' 123.8(14) . . ? F7' P2 F12' 86.8(16) . . ? F8' P2 F12' 86(2) . . ? F8 P2 F12' 83.8(13) . . ? F7 P2 F12' 100.6(10) . . ? F12 P2 F12' 52.0(12) . . ? F10' P2 F12' 179.3(17) . . ? F11' P2 F12' 87.8(15) . . ? F9 P2 F12' 140.3(17) . . ? F11 P2 F12' 40.6(10) . . ? F10 P2 F12' 130.1(17) . . ? F9' P2 F12' 90.3(19) . . ? N2 C1 N1 103.5(5) . . ? N2 C1 Fe1 143.1(5) . . ? N1 C1 Fe1 113.4(4) . . ? C3 C2 N2 110.1(7) . . ? C3 C2 H2 125.0 . . ? N2 C2 H2 125.0 . . ? C2 C3 N1 104.4(7) . . ? C2 C3 H3 127.8 . . ? N1 C3 H3 127.8 . . ? N4 C4 N3 129.1(7) . . ? N4 C4 N1 119.2(6) . . ? N3 C4 N1 111.6(5) . . ? N4 C5 C6 123.4(7) . . ? N4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C5 C6 C7 116.7(8) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? N3 C7 C6 122.2(7) . . ? N3 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N6 C9 N5 101.8(5) . . ? N6 C9 Fe1 144.1(4) . . ? N5 C9 Fe1 114.1(4) . . ? C11 C10 N6 108.3(6) . . ? C11 C10 H10 125.8 . . ? N6 C10 H10 125.8 . . ? C10 C11 N5 105.9(6) . . ? C10 C11 H11 127.0 . . ? N5 C11 H11 127.0 . . ? N8 C12 N7 128.9(6) . . ? N8 C12 N5 118.7(6) . . ? N7 C12 N5 112.4(5) . . ? N8 C13 C14 122.9(7) . . ? N8 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 117.9(7) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? N7 C15 C14 122.1(6) . . ? N7 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? N6 C16 H16A 109.5 . . ? N6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N9 C17 C18 178.1(9) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N10 C19 C20 177.6(8) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Fe1 N3 C7 -178.8(6) . . . . ? C9 Fe1 N3 C7 -88.8(6) . . . . ? N10 Fe1 N3 C7 89.6(6) . . . . ? N9 Fe1 N3 C7 3.7(6) . . . . ? N7 Fe1 N3 C7 -49(6) . . . . ? C1 Fe1 N3 C4 2.9(4) . . . . ? C9 Fe1 N3 C4 92.8(4) . . . . ? N10 Fe1 N3 C4 -88.7(4) . . . . ? N9 Fe1 N3 C4 -174.7(4) . . . . ? N7 Fe1 N3 C4 133(5) . . . . ? C1 Fe1 N7 C15 -91.6(6) . . . . ? C9 Fe1 N7 C15 178.9(6) . . . . ? N10 Fe1 N7 C15 0.3(6) . . . . ? N3 Fe1 N7 C15 138(5) . . . . ? N9 Fe1 N7 C15 86.1(6) . . . . ? C1 Fe1 N7 C12 95.1(4) . . . . ? C9 Fe1 N7 C12 5.6(4) . . . . ? N10 Fe1 N7 C12 -173.0(4) . . . . ? N3 Fe1 N7 C12 -35(6) . . . . ? N9 Fe1 N7 C12 -87.2(4) . . . . ? C1 Fe1 N9 C17 101(3) . . . . ? C9 Fe1 N9 C17 -141(3) . . . . ? N10 Fe1 N9 C17 34(3) . . . . ? N3 Fe1 N9 C17 122(3) . . . . ? N7 Fe1 N9 C17 -59(3) . . . . ? C1 Fe1 N10 C19 -130(11) . . . . ? C9 Fe1 N10 C19 117(11) . . . . ? N3 Fe1 N10 C19 -48(11) . . . . ? N9 Fe1 N10 C19 44(11) . . . . ? N7 Fe1 N10 C19 130(11) . . . . ? C2 N2 C1 N1 0.1(7) . . . . ? C8 N2 C1 N1 179.9(6) . . . . ? C2 N2 C1 Fe1 178.9(6) . . . . ? C8 N2 C1 Fe1 -1.3(12) . . . . ? C4 N1 C1 N2 180.0(5) . . . . ? C3 N1 C1 N2 -0.1(7) . . . . ? C4 N1 C1 Fe1 0.8(7) . . . . ? C3 N1 C1 Fe1 -179.3(5) . . . . ? C9 Fe1 C1 N2 82.3(7) . . . . ? N10 Fe1 C1 N2 -92.0(7) . . . . ? N3 Fe1 C1 N2 179.4(8) . . . . ? N9 Fe1 C1 N2 -159.1(15) . . . . ? N7 Fe1 C1 N2 1.0(8) . . . . ? C9 Fe1 C1 N1 -99.0(4) . . . . ? N10 Fe1 C1 N1 86.7(4) . . . . ? N3 Fe1 C1 N1 -1.9(4) . . . . ? N9 Fe1 C1 N1 20(2) . . . . ? N7 Fe1 C1 N1 179.7(4) . . . . ? C1 N2 C2 C3 -0.1(10) . . . . ? C8 N2 C2 C3 -179.9(8) . . . . ? N2 C2 C3 N1 0.0(10) . . . . ? C1 N1 C3 C2 0.1(9) . . . . ? C4 N1 C3 C2 179.9(7) . . . . ? C5 N4 C4 N3 -0.7(12) . . . . ? C5 N4 C4 N1 -178.6(7) . . . . ? C7 N3 C4 N4 0.3(10) . . . . ? Fe1 N3 C4 N4 178.9(6) . . . . ? C7 N3 C4 N1 178.3(5) . . . . ? Fe1 N3 C4 N1 -3.1(7) . . . . ? C1 N1 C4 N4 179.7(6) . . . . ? C3 N1 C4 N4 -0.1(11) . . . . ? C1 N1 C4 N3 1.5(8) . . . . ? C3 N1 C4 N3 -178.3(7) . . . . ? C4 N4 C5 C6 1.0(13) . . . . ? N4 C5 C6 C7 -0.8(14) . . . . ? C4 N3 C7 C6 0.0(9) . . . . ? Fe1 N3 C7 C6 -178.4(5) . . . . ? C5 C6 C7 N3 0.3(11) . . . . ? C10 N6 C9 N5 -0.8(7) . . . . ? C16 N6 C9 N5 178.3(6) . . . . ? C10 N6 C9 Fe1 -179.4(6) . . . . ? C16 N6 C9 Fe1 -0.3(11) . . . . ? C11 N5 C9 N6 1.0(7) . . . . ? C12 N5 C9 N6 -176.3(5) . . . . ? C11 N5 C9 Fe1 -179.9(5) . . . . ? C12 N5 C9 Fe1 2.8(7) . . . . ? C1 Fe1 C9 N6 74.4(8) . . . . ? N10 Fe1 C9 N6 -172.6(16) . . . . ? N3 Fe1 C9 N6 -7.2(8) . . . . ? N9 Fe1 C9 N6 -99.8(7) . . . . ? N7 Fe1 C9 N6 174.1(8) . . . . ? C1 Fe1 C9 N5 -104.1(4) . . . . ? N10 Fe1 C9 N5 9(2) . . . . ? N3 Fe1 C9 N5 174.3(4) . . . . ? N9 Fe1 C9 N5 81.7(4) . . . . ? N7 Fe1 C9 N5 -4.4(4) . . . . ? C9 N6 C10 C11 0.4(9) . . . . ? C16 N6 C10 C11 -178.7(7) . . . . ? N6 C10 C11 N5 0.2(9) . . . . ? C9 N5 C11 C10 -0.8(9) . . . . ? C12 N5 C11 C10 176.1(7) . . . . ? C13 N8 C12 N7 1.2(11) . . . . ? C13 N8 C12 N5 -179.2(6) . . . . ? C15 N7 C12 N8 -0.3(10) . . . . ? Fe1 N7 C12 N8 174.1(6) . . . . ? C15 N7 C12 N5 -179.9(5) . . . . ? Fe1 N7 C12 N5 -5.5(7) . . . . ? C11 N5 C12 N8 5.5(11) . . . . ? C9 N5 C12 N8 -177.8(6) . . . . ? C11 N5 C12 N7 -174.9(7) . . . . ? C9 N5 C12 N7 1.9(8) . . . . ? C12 N8 C13 C14 -0.6(12) . . . . ? N8 C13 C14 C15 -0.8(14) . . . . ? C12 N7 C15 C14 -1.2(10) . . . . ? Fe1 N7 C15 C14 -174.5(6) . . . . ? C13 C14 C15 N7 1.7(12) . . . . ? Fe1 N9 C17 C18 147(24) . . . . ? Fe1 N10 C19 C20 -44(26) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.667 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.079 #===END data_090708g _database_code_depnum_ccdc_archive 'CCDC 782459' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 F12 Fe N10 P2' _chemical_formula_weight 872.40 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbcn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.9083(13) _cell_length_b 17.3384(17) _cell_length_c 15.1390(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3388.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.648 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.884 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 13113 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2981 _reflns_number_gt 1550 _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^)+(0.1669P)^2^+16.5167P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2981 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1753 _refine_ls_R_factor_gt 0.1025 _refine_ls_wR_factor_ref 0.3670 _refine_ls_wR_factor_gt 0.2595 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 Fe1 Fe 0.5000 0.42156(9) 0.2500 0.0418(7) Uani 1 2 d S . . N1 N 0.5621(6) 0.5135(4) 0.1093(5) 0.048(2) Uani 1 1 d . . . N2 N 0.4163(6) 0.5619(4) 0.1438(5) 0.050(2) Uani 1 1 d . . . N3 N 0.6397(6) 0.4197(4) 0.1917(5) 0.0484(19) Uani 1 1 d . . . N4 N 0.7277(6) 0.4732(5) 0.0672(6) 0.059(2) Uani 1 1 d . . . N5 N 0.4573(6) 0.3389(5) 0.1678(5) 0.0486(19) Uani 1 1 d . . . P1 P 0.8847(4) 0.6658(3) 0.9330(4) 0.1189(17) Uani 1 1 d . . . F1 F 0.9820(11) 0.7081(8) 0.8989(10) 0.185(5) Uani 1 1 d . . . F2 F 0.7751(6) 0.6339(5) 0.9352(7) 0.114(3) Uani 1 1 d . . . F3 F 0.8462(12) 0.7156(8) 0.8582(9) 0.192(5) Uani 1 1 d . . . F4 F 0.8669(6) 0.7270(4) 1.0034(5) 0.096(2) Uani 1 1 d . . . F5 F 0.9386(7) 0.6089(5) 0.9865(8) 0.138(4) Uani 1 1 d . . . F6 F 0.9183(13) 0.6052(10) 0.8626(12) 0.214(6) Uani 1 1 d . . . C1 C 0.4811(7) 0.5026(5) 0.1662(6) 0.045(2) Uani 1 1 d . . . C2 C 0.4597(8) 0.6074(6) 0.0769(7) 0.056(3) Uani 1 1 d . . . H2 H 0.4303 0.6513 0.0521 0.067 Uiso 1 1 calc R . . C3 C 0.5491(8) 0.5771(5) 0.0558(7) 0.056(3) Uani 1 1 d . . . H3 H 0.5949 0.5949 0.0130 0.067 Uiso 1 1 calc R . . C4 C 0.6506(7) 0.4657(5) 0.1224(7) 0.049(2) Uani 1 1 d . . . C5 C 0.8084(9) 0.4287(7) 0.0870(8) 0.067(3) Uani 1 1 d . . . H5 H 0.8674 0.4315 0.0518 0.081 Uiso 1 1 calc R . . C6 C 0.8080(9) 0.3803(7) 0.1555(8) 0.069(3) Uani 1 1 d . . . H6 H 0.8653 0.3494 0.1673 0.082 Uiso 1 1 calc R . . C7 C 0.7237(8) 0.3766(6) 0.2072(8) 0.061(3) Uani 1 1 d . . . H7 H 0.7236 0.3432 0.2552 0.073 Uiso 1 1 calc R . . C8 C 0.3220(8) 0.5783(6) 0.1899(7) 0.055(3) Uani 1 1 d . . . C9 C 0.2349(8) 0.5376(6) 0.1716(8) 0.063(3) Uani 1 1 d . . . H9 H 0.2347 0.5003 0.1275 0.076 Uiso 1 1 calc R . . C10 C 0.1467(10) 0.5528(8) 0.2200(9) 0.078(3) Uani 1 1 d . . . H10 H 0.0872 0.5238 0.2105 0.094 Uiso 1 1 calc R . . C11 C 0.1462(11) 0.6110(8) 0.2824(9) 0.086(4) Uani 1 1 d . . . H11 H 0.0859 0.6216 0.3137 0.103 Uiso 1 1 calc R . . C12 C 0.2327(10) 0.6522(7) 0.2981(9) 0.080(4) Uani 1 1 d . . . H12 H 0.2322 0.6911 0.3404 0.096 Uiso 1 1 calc R . . C13 C 0.3203(9) 0.6370(6) 0.2519(8) 0.067(3) Uani 1 1 d . . . H13 H 0.3796 0.6661 0.2620 0.080 Uiso 1 1 calc R . . C14 C 0.4273(7) 0.2892(6) 0.1259(7) 0.054(2) Uani 1 1 d . . . C15 C 0.3863(9) 0.2271(6) 0.0739(8) 0.074(3) Uani 1 1 d . . . H15A H 0.3651 0.1858 0.1121 0.111 Uiso 1 1 calc R . . H15B H 0.4386 0.2088 0.0340 0.111 Uiso 1 1 calc R . . H15C H 0.3277 0.2451 0.0407 0.111 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 Fe1 0.0414(11) 0.0382(10) 0.0459(12) 0.000 0.0028(8) 0.000 N1 0.051(5) 0.049(5) 0.045(5) 0.000(4) 0.011(4) -0.003(4) N2 0.050(4) 0.045(4) 0.053(5) 0.004(4) 0.009(4) 0.006(3) N3 0.051(5) 0.045(4) 0.050(5) -0.007(4) 0.000(4) 0.002(4) N4 0.048(5) 0.070(5) 0.061(6) -0.003(4) 0.015(4) 0.002(4) N5 0.050(4) 0.049(5) 0.046(5) 0.004(4) 0.001(4) 0.001(4) P1 0.105(4) 0.111(3) 0.140(4) -0.008(3) -0.013(3) -0.009(3) F1 0.174(12) 0.168(11) 0.212(14) -0.003(10) 0.066(10) -0.012(9) F2 0.069(5) 0.096(5) 0.178(9) -0.016(6) -0.012(5) -0.019(4) F3 0.220(15) 0.187(12) 0.167(11) 0.052(10) -0.019(11) -0.023(11) F4 0.103(6) 0.086(5) 0.098(5) -0.022(4) 0.013(4) -0.009(4) F5 0.107(7) 0.100(6) 0.207(11) 0.017(7) -0.025(7) 0.029(5) F6 0.209(14) 0.198(14) 0.236(16) -0.051(13) 0.016(14) 0.014(11) C1 0.047(5) 0.042(5) 0.045(6) -0.004(4) 0.004(4) 0.003(4) C2 0.060(6) 0.053(6) 0.054(7) 0.011(5) 0.005(5) 0.003(5) C3 0.064(6) 0.051(6) 0.053(6) 0.009(5) 0.014(5) 0.002(5) C4 0.047(5) 0.050(5) 0.050(6) -0.006(5) 0.004(4) 0.001(4) C5 0.053(6) 0.079(8) 0.069(8) -0.010(6) 0.019(6) 0.005(6) C6 0.058(7) 0.071(7) 0.076(8) -0.008(6) 0.015(6) 0.013(6) C7 0.052(6) 0.066(7) 0.065(7) 0.003(6) 0.005(5) 0.005(5) C8 0.053(6) 0.053(6) 0.060(7) 0.008(5) 0.011(5) 0.013(5) C9 0.054(6) 0.061(6) 0.074(8) 0.001(6) 0.007(6) 0.007(5) C10 0.063(7) 0.078(8) 0.094(9) 0.005(7) 0.015(7) 0.005(6) C11 0.075(9) 0.090(9) 0.091(10) 0.013(8) 0.024(7) 0.021(7) C12 0.081(9) 0.076(8) 0.084(9) -0.004(7) 0.019(7) 0.017(7) C13 0.066(7) 0.064(6) 0.071(7) 0.000(6) 0.009(6) 0.011(5) C14 0.047(5) 0.052(6) 0.062(7) -0.003(5) 0.008(5) 0.003(4) C15 0.080(8) 0.059(6) 0.082(8) -0.021(6) 0.002(7) -0.010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 C1 1.908(9) . ? Fe1 C1 1.908(9) 3_655 ? Fe1 N5 1.976(9) . ? Fe1 N5 1.976(8) 3_655 ? Fe1 N3 2.008(8) . ? Fe1 N3 2.008(8) 3_655 ? N1 C1 1.368(11) . ? N1 C3 1.378(12) . ? N1 C4 1.425(12) . ? N2 C1 1.369(11) . ? N2 C2 1.401(12) . ? N2 C8 1.431(12) . ? N3 C4 1.326(12) . ? N3 C7 1.336(12) . ? N4 C4 1.306(12) . ? N4 C5 1.331(13) . ? N5 C14 1.138(12) . ? P1 F5 1.453(10) . ? P1 F3 1.508(14) . ? P1 F2 1.519(8) . ? P1 F4 1.522(8) . ? P1 F1 1.543(13) . ? P1 F6 1.559(15) . ? C2 C3 1.308(14) . ? C5 C6 1.334(16) . ? C6 C7 1.343(14) . ? C8 C9 1.356(14) . ? C8 C13 1.385(14) . ? C9 C10 1.380(15) . ? C10 C11 1.382(19) . ? C11 C12 1.347(18) . ? C12 C13 1.355(15) . ? C14 C15 1.436(15) . ? 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 C1 Fe1 C1 85.2(5) . 3_655 ? C1 Fe1 N5 94.6(3) . . ? C1 Fe1 N5 171.1(3) 3_655 . ? C1 Fe1 N5 171.1(3) . 3_655 ? C1 Fe1 N5 94.6(3) 3_655 3_655 ? N5 Fe1 N5 87.1(4) . 3_655 ? C1 Fe1 N3 80.5(3) . . ? C1 Fe1 N3 100.9(3) 3_655 . ? N5 Fe1 N3 87.8(3) . . ? N5 Fe1 N3 90.8(3) 3_655 . ? C1 Fe1 N3 100.9(3) . 3_655 ? C1 Fe1 N3 80.5(3) 3_655 3_655 ? N5 Fe1 N3 90.8(3) . 3_655 ? N5 Fe1 N3 87.8(3) 3_655 3_655 ? N3 Fe1 N3 178.1(4) . 3_655 ? C1 N1 C3 112.8(8) . . ? C1 N1 C4 116.4(8) . . ? C3 N1 C4 130.1(8) . . ? C1 N2 C2 111.0(8) . . ? C1 N2 C8 123.3(8) . . ? C2 N2 C8 125.5(8) . . ? C4 N3 C7 112.9(8) . . ? C4 N3 Fe1 115.6(6) . . ? C7 N3 Fe1 131.4(7) . . ? C4 N4 C5 113.3(9) . . ? C14 N5 Fe1 174.3(8) . . ? F5 P1 F3 164.6(9) . . ? F5 P1 F2 100.8(6) . . ? F3 P1 F2 85.3(7) . . ? F5 P1 F4 99.0(6) . . ? F3 P1 F4 94.4(7) . . ? F2 P1 F4 95.6(5) . . ? F5 P1 F1 96.8(8) . . ? F3 P1 F1 75.2(8) . . ? F2 P1 F1 159.7(8) . . ? F4 P1 F1 91.5(7) . . ? F5 P1 F6 77.8(8) . . ? F3 P1 F6 87.9(10) . . ? F2 P1 F6 91.6(8) . . ? F4 P1 F6 172.5(8) . . ? F1 P1 F6 82.2(8) . . ? N1 C1 N2 101.9(8) . . ? N1 C1 Fe1 115.0(6) . . ? N2 C1 Fe1 142.8(7) . . ? C3 C2 N2 107.6(9) . . ? C2 C3 N1 106.6(9) . . ? N4 C4 N3 130.3(9) . . ? N4 C4 N1 117.7(9) . . ? N3 C4 N1 112.1(8) . . ? N4 C5 C6 122.4(10) . . ? C5 C6 C7 119.1(11) . . ? N3 C7 C6 122.0(11) . . ? C9 C8 C13 120.5(10) . . ? C9 C8 N2 120.2(9) . . ? C13 C8 N2 119.3(10) . . ? C8 C9 C10 118.5(11) . . ? C9 C10 C11 120.4(12) . . ? C12 C11 C10 120.3(12) . . ? C11 C12 C13 119.8(13) . . ? C12 C13 C8 120.4(12) . . ? N5 C14 C15 178.2(11) . . ? 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 C1 Fe1 N3 C4 -6.0(6) . . . . ? C1 Fe1 N3 C4 -89.2(7) 3_655 . . . ? N5 Fe1 N3 C4 89.0(7) . . . . ? N5 Fe1 N3 C4 176.0(7) 3_655 . . . ? N3 Fe1 N3 C4 132.5(6) 3_655 . . . ? C1 Fe1 N3 C7 178.3(9) . . . . ? C1 Fe1 N3 C7 95.1(9) 3_655 . . . ? N5 Fe1 N3 C7 -86.7(9) . . . . ? N5 Fe1 N3 C7 0.3(9) 3_655 . . . ? N3 Fe1 N3 C7 -43.2(9) 3_655 . . . ? C1 Fe1 N5 C14 -130(8) . . . . ? C1 Fe1 N5 C14 -42(9) 3_655 . . . ? N5 Fe1 N5 C14 59(8) 3_655 . . . ? N3 Fe1 N5 C14 149(8) . . . . ? N3 Fe1 N5 C14 -29(8) 3_655 . . . ? C3 N1 C1 N2 1.1(10) . . . . ? C4 N1 C1 N2 172.8(7) . . . . ? C3 N1 C1 Fe1 -174.2(6) . . . . ? C4 N1 C1 Fe1 -2.5(10) . . . . ? C2 N2 C1 N1 -1.4(10) . . . . ? C8 N2 C1 N1 -175.7(9) . . . . ? C2 N2 C1 Fe1 171.6(9) . . . . ? C8 N2 C1 Fe1 -2.6(17) . . . . ? C1 Fe1 C1 N1 106.3(8) 3_655 . . . ? N5 Fe1 C1 N1 -82.6(7) . . . . ? N5 Fe1 C1 N1 18(3) 3_655 . . . ? N3 Fe1 C1 N1 4.4(6) . . . . ? N3 Fe1 C1 N1 -174.3(6) 3_655 . . . ? C1 Fe1 C1 N2 -66.2(10) 3_655 . . . ? N5 Fe1 C1 N2 104.9(11) . . . . ? N5 Fe1 C1 N2 -155.0(18) 3_655 . . . ? N3 Fe1 C1 N2 -168.1(12) . . . . ? N3 Fe1 C1 N2 13.2(12) 3_655 . . . ? C1 N2 C2 C3 1.3(11) . . . . ? C8 N2 C2 C3 175.4(10) . . . . ? N2 C2 C3 N1 -0.5(11) . . . . ? C1 N1 C3 C2 -0.4(12) . . . . ? C4 N1 C3 C2 -170.7(9) . . . . ? C5 N4 C4 N3 -2.5(15) . . . . ? C5 N4 C4 N1 177.2(9) . . . . ? C7 N3 C4 N4 2.3(15) . . . . ? Fe1 N3 C4 N4 -174.2(9) . . . . ? C7 N3 C4 N1 -177.4(8) . . . . ? Fe1 N3 C4 N1 6.1(10) . . . . ? C1 N1 C4 N4 177.8(8) . . . . ? C3 N1 C4 N4 -12.3(15) . . . . ? C1 N1 C4 N3 -2.4(11) . . . . ? C3 N1 C4 N3 167.5(9) . . . . ? C4 N4 C5 C6 1.6(16) . . . . ? N4 C5 C6 C7 -0.8(18) . . . . ? C4 N3 C7 C6 -1.1(14) . . . . ? Fe1 N3 C7 C6 174.6(8) . . . . ? C5 C6 C7 N3 0.5(17) . . . . ? C1 N2 C8 C9 -81.3(13) . . . . ? C2 N2 C8 C9 105.3(12) . . . . ? C1 N2 C8 C13 99.9(11) . . . . ? C2 N2 C8 C13 -73.5(13) . . . . ? C13 C8 C9 C10 -3.9(16) . . . . ? N2 C8 C9 C10 177.3(10) . . . . ? C8 C9 C10 C11 3.2(18) . . . . ? C9 C10 C11 C12 -2(2) . . . . ? C10 C11 C12 C13 0(2) . . . . ? C11 C12 C13 C8 -1.1(19) . . . . ? C9 C8 C13 C12 2.9(17) . . . . ? N2 C8 C13 C12 -178.2(10) . . . . ? Fe1 N5 C14 C15 45(43) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.145 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.152 #===END data_09 _database_code_depnum_ccdc_archive 'CCDC 782460' #TrackingRef '- cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H29 F12 Fe N11 P2' _chemical_formula_weight 913.45 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6700(19) _cell_length_b 12.620(3) _cell_length_c 17.400(4) _cell_angle_alpha 99.94(3) _cell_angle_beta 100.94(3) _cell_angle_gamma 110.39(3) _cell_volume 1887.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8484 _exptl_absorpt_correction_T_max 0.8819 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 9579 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0945 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6456 _reflns_number_gt 3422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SMART' _computing_publication_material 'Bruker SMART' _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^)+(0.2000P)^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 6456 _refine_ls_number_parameters 501 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1615 _refine_ls_R_factor_gt 0.1144 _refine_ls_wR_factor_ref 0.3609 _refine_ls_wR_factor_gt 0.3355 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 C1 C 0.5656(14) 0.8413(9) 0.6336(7) 0.075(3) Uani 1 1 d . . . C2 C 0.9781(11) 0.8693(8) 0.5698(5) 0.057(2) Uani 1 1 d . . . C3 C 1.0963(10) 1.1623(7) 0.7655(5) 0.052(2) Uani 1 1 d . . . C5 C 1.1147(11) 0.9903(7) 0.7936(5) 0.052(2) Uani 1 1 d . . . C7 C 0.8528(10) 0.9424(7) 0.8349(5) 0.050(2) Uani 1 1 d . . . C9 C 0.8063(12) 0.7426(7) 0.8125(5) 0.062(2) Uani 1 1 d . . . C12 C 1.1547(13) 1.2741(8) 0.7634(7) 0.076(3) Uani 1 1 d . . . H12 H 1.2559 1.3218 0.7912 0.092 Uiso 1 1 calc R . . C13 C 1.0640(15) 1.3181(8) 0.7198(6) 0.077(3) Uani 1 1 d . . . H13 H 1.1020 1.3955 0.7171 0.093 Uiso 1 1 calc R . . C14 C 0.8691(11) 1.1309(8) 0.6835(6) 0.060(2) Uani 1 1 d . . . H14 H 0.7698 1.0803 0.6541 0.072 Uiso 1 1 calc R . . C15 C 0.9142(14) 1.2432(8) 0.6800(6) 0.072(3) Uani 1 1 d . . . H15 H 0.8467 1.2696 0.6518 0.087 Uiso 1 1 calc R . . C16 C 1.3273(13) 1.1571(9) 0.8573(7) 0.078(3) Uani 1 1 d . . . H16 H 1.3938 1.2355 0.8739 0.094 Uiso 1 1 calc R . . C17 C 1.3542(12) 1.0665(10) 0.8773(6) 0.077(3) Uani 1 1 d . . . H17 H 1.4427 1.0710 0.9123 0.092 Uiso 1 1 calc R . . C18 C 1.2267(12) 0.8542(9) 0.8364(6) 0.069(3) Uani 1 1 d . . . C20 C 1.276(2) 0.7333(12) 0.9082(8) 0.123(6) Uani 1 1 d . . . H20 H 1.2990 0.7170 0.9581 0.148 Uiso 1 1 calc R . . C21 C 0.7774(14) 0.8635(8) 0.9349(6) 0.077(3) Uani 1 1 d . . . H21 H 0.7428 0.8088 0.9638 0.092 Uiso 1 1 calc R . . C22 C 0.8025(15) 0.9735(10) 0.9550(6) 0.085(3) Uani 1 1 d . . . H22 H 0.7949 1.0134 1.0032 0.102 Uiso 1 1 calc R . . C23 C 0.7571(16) 0.6334(8) 0.8283(6) 0.091(4) Uani 1 1 d . . . H23 H 0.7350 0.6253 0.8772 0.109 Uiso 1 1 calc R . . C25 C 0.8592(11) 1.1383(7) 0.8934(5) 0.055(2) Uani 1 1 d . . . C26 C 0.7476(13) 1.1586(10) 0.8487(7) 0.084(3) Uani 1 1 d . . . H26 H 0.6601 1.0977 0.8139 0.100 Uiso 1 1 calc R . . C27 C 1.0084(17) 1.3312(9) 0.9450(9) 0.108(4) Uani 1 1 d . . . H27 H 1.0990 1.3906 0.9783 0.129 Uiso 1 1 calc R . . C28 C 0.8997(16) 1.3613(9) 0.9033(7) 0.086(3) Uani 1 1 d . . . H28 H 0.9160 1.4394 0.9072 0.103 Uiso 1 1 calc R . . C29 C 1.0100(14) 0.8449(10) 0.4938(6) 0.081(3) Uani 1 1 d . . . H29A H 0.9282 0.8424 0.4516 0.122 Uiso 1 1 calc R . . H29B H 1.0191 0.7707 0.4842 0.122 Uiso 1 1 calc R . . H29C H 1.1044 0.9052 0.4943 0.122 Uiso 1 1 calc R . . C30 C 0.4153(13) 0.8079(14) 0.5858(9) 0.122(5) Uani 1 1 d . . . H30A H 0.3746 0.8636 0.6051 0.183 Uiso 1 1 calc R . . H30B H 0.3524 0.7318 0.5892 0.183 Uiso 1 1 calc R . . H30C H 0.4161 0.8055 0.5304 0.183 Uiso 1 1 calc R . . C31 C 0.7676(17) 1.2742(11) 0.8563(9) 0.104(4) Uani 1 1 d . . . H31 H 0.6898 1.2921 0.8288 0.125 Uiso 1 1 calc R . . C32 C 1.192(2) 0.7708(13) 0.7662(7) 0.129(6) Uani 1 1 d . . . H32 H 1.1556 0.7830 0.7164 0.155 Uiso 1 1 calc R . . C33 C 1.209(2) 0.6746(14) 0.7696(9) 0.154(8) Uani 1 1 d . . . H33 H 1.1905 0.6191 0.7219 0.185 Uiso 1 1 calc R . . C34 C 1.255(3) 0.6539(15) 0.8423(10) 0.190(11) Uani 1 1 d . . . H34 H 1.2710 0.5860 0.8454 0.228 Uiso 1 1 calc R . . C35 C 0.742(2) 0.5405(10) 0.7726(8) 0.120(5) Uani 1 1 d . . . H35 H 0.7025 0.4656 0.7801 0.144 Uiso 1 1 calc R . . C36 C 0.7861(19) 0.5583(10) 0.7037(9) 0.116(5) Uani 1 1 d . . . H36 H 0.7775 0.4940 0.6648 0.140 Uiso 1 1 calc R . . C37 C 0.8410(17) 0.6643(8) 0.6906(7) 0.102(4) Uani 1 1 d . . . H37 H 0.8737 0.6729 0.6443 0.122 Uiso 1 1 calc R . . F1 F 0.4186(13) 0.7480(12) 0.3820(11) 0.234(7) Uani 1 1 d . . . F2 F -0.0542(13) 0.3794(7) 0.4365(5) 0.156(4) Uani 1 1 d . . . F3 F 0.4009(11) 0.3760(6) 0.0047(5) 0.141(3) Uani 1 1 d . . . F4 F 0.4072(15) 0.5578(8) 0.0407(12) 0.229(8) Uani 1 1 d . . . F5 F 0.6496(19) 0.7819(19) 0.4266(13) 0.318(12) Uani 1 1 d . . . F6 F 0.616(3) 0.9265(14) 0.4532(10) 0.292(10) Uani 1 1 d . . . F7 F 0.7297(13) 0.9045(13) 0.3650(8) 0.227(7) Uani 1 1 d . . . F8 F 0.504(2) 0.9087(13) 0.3340(12) 0.280(10) Uani 1 1 d . . . F9 F 0.5413(17) 0.7554(11) 0.2928(8) 0.215(6) Uani 1 1 d . . . F10 F 0.583(2) 0.5260(10) 0.0847(7) 0.268(10) Uani 1 1 d . . . F11 F 0.007(3) 0.5593(13) 0.4348(8) 0.281(11) Uani 1 1 d . . . F12 F 0.1498(14) 0.5142(19) 0.4968(14) 0.310(12) Uani 1 1 d . . . Fe1 Fe 0.90305(14) 0.92316(9) 0.73386(7) 0.0499(5) Uani 1 1 d . . . N1 N 0.6887(10) 0.8742(6) 0.6718(5) 0.0572(18) Uani 1 1 d . . . N2 N 0.9509(8) 0.8854(6) 0.6299(4) 0.0526(17) Uani 1 1 d . . . N3 N 0.9532(8) 1.0865(5) 0.7248(4) 0.0439(15) Uani 1 1 d . . . N4 N 0.8493(10) 0.7595(6) 0.7442(5) 0.067(2) Uani 1 1 d . . . N5 N 0.8426(9) 1.0219(6) 0.8930(4) 0.0565(18) Uani 1 1 d . . . N6 N 0.8125(9) 0.8432(6) 0.8612(4) 0.062(2) Uani 1 1 d . . . N7 N 1.1800(9) 1.1088(6) 0.8067(4) 0.0565(18) Uani 1 1 d . . . N8 N 1.2273(9) 0.9659(7) 0.8366(4) 0.0607(19) Uani 1 1 d . . . N9 N 0.9910(10) 1.2225(7) 0.9404(6) 0.087(3) Uani 1 1 d . . . N10 N 1.2671(15) 0.8364(9) 0.9069(5) 0.104(4) Uani 1 1 d . . . P1 P 0.5000 0.5000 0.0000 0.0606(9) Uani 1 2 d S . . P2 P 0.0000 0.5000 0.5000 0.0698(11) Uani 1 2 d S . . P3 P 0.5762(4) 0.8408(4) 0.3770(2) 0.0967(11) 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 C1 0.072(8) 0.060(6) 0.083(7) 0.016(6) 0.022(6) 0.013(6) C2 0.071(6) 0.059(5) 0.044(5) 0.006(4) 0.008(4) 0.034(5) C3 0.067(6) 0.044(5) 0.059(5) 0.022(4) 0.025(5) 0.029(5) C5 0.082(6) 0.045(5) 0.045(4) 0.016(4) 0.031(4) 0.034(4) C7 0.068(6) 0.043(4) 0.045(4) 0.020(4) 0.018(4) 0.024(4) C9 0.091(7) 0.034(4) 0.060(5) 0.018(4) 0.031(5) 0.017(4) C12 0.084(7) 0.041(5) 0.078(7) 0.007(5) 0.004(6) 0.007(5) C13 0.129(10) 0.038(5) 0.072(6) 0.018(5) 0.032(7) 0.038(6) C14 0.066(6) 0.052(5) 0.070(6) 0.027(5) 0.026(5) 0.021(5) C15 0.102(8) 0.053(6) 0.073(6) 0.028(5) 0.027(6) 0.037(6) C16 0.080(8) 0.047(5) 0.088(8) 0.013(5) 0.015(6) 0.010(5) C17 0.063(7) 0.085(8) 0.068(7) 0.011(6) 0.002(5) 0.024(6) C18 0.089(7) 0.063(6) 0.053(5) 0.004(5) 0.006(5) 0.040(5) C20 0.224(18) 0.104(10) 0.071(8) 0.038(8) 0.024(10) 0.100(12) C21 0.131(10) 0.050(6) 0.059(6) 0.028(5) 0.045(6) 0.030(6) C22 0.134(10) 0.076(7) 0.060(6) 0.029(5) 0.061(7) 0.036(7) C23 0.170(12) 0.048(6) 0.066(6) 0.029(5) 0.046(7) 0.041(7) C25 0.071(6) 0.045(5) 0.045(5) 0.004(4) 0.026(4) 0.017(4) C26 0.079(8) 0.065(7) 0.085(8) 0.012(6) -0.006(6) 0.021(6) C27 0.109(10) 0.040(6) 0.141(12) -0.002(7) 0.012(9) 0.015(6) C28 0.115(10) 0.047(6) 0.088(8) 0.007(6) 0.018(7) 0.033(7) C29 0.127(10) 0.083(7) 0.050(5) 0.020(5) 0.039(6) 0.052(7) C30 0.060(8) 0.137(13) 0.125(12) 0.026(10) -0.012(8) 0.010(8) C31 0.113(11) 0.077(8) 0.125(11) 0.033(8) 0.012(9) 0.048(8) C32 0.238(19) 0.111(10) 0.057(7) 0.013(7) 0.001(9) 0.115(12) C33 0.28(2) 0.126(12) 0.083(9) -0.001(9) 0.000(12) 0.156(15) C34 0.36(3) 0.133(13) 0.096(11) -0.004(10) -0.041(14) 0.182(18) C35 0.225(17) 0.050(6) 0.084(8) 0.024(6) 0.043(10) 0.049(9) C36 0.205(16) 0.049(6) 0.114(10) 0.025(7) 0.083(11) 0.052(8) C37 0.181(13) 0.032(5) 0.091(8) 0.015(5) 0.052(9) 0.033(7) F1 0.131(9) 0.195(12) 0.327(18) 0.036(12) 0.084(10) 0.011(8) F2 0.241(11) 0.071(5) 0.115(6) -0.012(4) 0.061(7) 0.025(6) F3 0.191(9) 0.051(4) 0.157(7) 0.028(4) 0.090(7) -0.001(4) F4 0.203(12) 0.098(7) 0.42(2) 0.051(10) 0.192(14) 0.054(7) F5 0.194(14) 0.34(2) 0.41(3) 0.25(2) -0.030(15) 0.086(15) F6 0.46(3) 0.202(14) 0.180(13) -0.020(11) 0.167(17) 0.080(17) F7 0.124(8) 0.273(15) 0.192(11) 0.025(11) 0.067(8) -0.024(9) F8 0.282(18) 0.181(12) 0.34(2) 0.020(13) -0.071(15) 0.155(13) F9 0.248(14) 0.165(11) 0.160(10) -0.026(9) 0.024(10) 0.043(10) F10 0.39(2) 0.132(9) 0.120(8) 0.031(7) -0.089(11) 0.002(12) F11 0.64(4) 0.188(12) 0.140(9) 0.100(9) 0.168(16) 0.245(19) F12 0.101(8) 0.33(2) 0.35(2) -0.085(19) 0.051(11) 0.006(10) Fe1 0.0700(9) 0.0359(7) 0.0450(7) 0.0122(5) 0.0227(6) 0.0175(6) N1 0.068(5) 0.041(4) 0.060(5) 0.015(4) 0.023(4) 0.015(4) N2 0.063(5) 0.046(4) 0.044(4) 0.009(3) 0.009(3) 0.021(3) N3 0.053(4) 0.040(3) 0.043(4) 0.015(3) 0.018(3) 0.018(3) N4 0.092(6) 0.052(4) 0.058(5) 0.015(4) 0.025(4) 0.026(4) N5 0.076(5) 0.054(4) 0.044(4) 0.011(3) 0.024(4) 0.026(4) N6 0.092(6) 0.041(4) 0.049(4) 0.015(3) 0.028(4) 0.017(4) N7 0.063(5) 0.049(4) 0.052(4) 0.013(3) 0.010(4) 0.019(4) N8 0.081(6) 0.061(5) 0.047(4) 0.015(4) 0.023(4) 0.032(4) N9 0.072(6) 0.049(5) 0.118(8) 0.005(5) 0.001(5) 0.018(4) N10 0.192(11) 0.090(7) 0.054(5) 0.026(5) 0.027(6) 0.083(8) P1 0.061(2) 0.0432(17) 0.062(2) 0.0167(16) 0.0067(17) 0.0074(16) P2 0.089(3) 0.0467(19) 0.073(2) 0.0122(18) 0.031(2) 0.0224(19) P3 0.076(2) 0.109(3) 0.088(2) 0.012(2) 0.0059(17) 0.030(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 C1 N1 1.137(13) . ? C1 C30 1.405(16) . ? C2 N2 1.128(10) . ? C2 C29 1.422(12) . ? C3 C12 1.335(12) . ? C3 N3 1.343(11) . ? C3 N7 1.397(10) . ? C5 N8 1.358(11) . ? C5 N7 1.363(11) . ? C5 Fe1 1.915(10) . ? C7 N5 1.340(10) . ? C7 N6 1.361(10) . ? C7 Fe1 1.910(8) . ? C9 N4 1.358(11) . ? C9 N6 1.375(11) . ? C9 C23 1.388(12) . ? C12 C13 1.373(14) . ? C12 H12 0.9300 . ? C13 C15 1.382(15) . ? C13 H13 0.9300 . ? C14 N3 1.313(11) . ? C14 C15 1.347(12) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.343(15) . ? C16 N7 1.382(12) . ? C16 H16 0.9300 . ? C17 N8 1.375(13) . ? C17 H17 0.9300 . ? C18 N10 1.297(12) . ? C18 C32 1.366(14) . ? C18 N8 1.407(12) . ? C20 C34 1.316(18) . ? C20 N10 1.340(14) . ? C20 H20 0.9300 . ? C21 C22 1.294(14) . ? C21 N6 1.391(11) . ? C21 H21 0.9300 . ? C22 N5 1.382(11) . ? C22 H22 0.9300 . ? C23 C35 1.330(14) . ? C23 H23 0.9300 . ? C25 C26 1.334(14) . ? C25 N9 1.336(12) . ? C25 N5 1.419(11) . ? C26 C31 1.382(15) . ? C26 H26 0.9300 . ? C27 N9 1.308(14) . ? C27 C28 1.364(17) . ? C27 H27 0.9300 . ? C28 C31 1.350(16) . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31 0.9300 . ? C32 C33 1.293(17) . ? C32 H32 0.9300 . ? C33 C34 1.359(19) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.375(17) . ? C35 H35 0.9300 . ? C36 C37 1.334(15) . ? C36 H36 0.9300 . ? C37 N4 1.355(12) . ? C37 H37 0.9300 . ? F1 P3 1.595(12) . ? F2 P2 1.567(7) . ? F3 P1 1.550(6) . ? F4 P1 1.536(10) . ? F5 P3 1.469(13) . ? F6 P3 1.448(12) . ? F7 P3 1.496(10) . ? F8 P3 1.492(13) . ? F9 P3 1.560(11) . ? F10 P1 1.458(10) . ? F11 P2 1.462(10) . ? F12 P2 1.409(13) . ? Fe1 N1 1.967(9) . ? Fe1 N2 1.971(7) . ? Fe1 N3 1.989(6) . ? Fe1 N4 1.996(8) . ? P1 F10 1.458(10) 2_665 ? P1 F4 1.536(10) 2_665 ? P1 F3 1.550(6) 2_665 ? P2 F12 1.409(13) 2_566 ? P2 F11 1.462(10) 2_566 ? P2 F2 1.567(7) 2_566 ? 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 C1 C30 176.3(12) . . ? N2 C2 C29 178.1(10) . . ? C12 C3 N3 124.0(8) . . ? C12 C3 N7 123.8(9) . . ? N3 C3 N7 112.1(7) . . ? N8 C5 N7 103.1(8) . . ? N8 C5 Fe1 143.3(6) . . ? N7 C5 Fe1 113.2(6) . . ? N5 C7 N6 104.0(7) . . ? N5 C7 Fe1 142.3(6) . . ? N6 C7 Fe1 113.7(6) . . ? N4 C9 N6 112.9(7) . . ? N4 C9 C23 122.3(8) . . ? N6 C9 C23 124.8(8) . . ? C3 C12 C13 119.5(10) . . ? C3 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C15 117.7(9) . . ? C12 C13 H13 121.2 . . ? C15 C13 H13 121.2 . . ? N3 C14 C15 125.6(10) . . ? N3 C14 H14 117.2 . . ? C15 C14 H14 117.2 . . ? C14 C15 C13 117.9(10) . . ? C14 C15 H15 121.1 . . ? C13 C15 H15 121.1 . . ? C17 C16 N7 105.4(9) . . ? C17 C16 H16 127.3 . . ? N7 C16 H16 127.3 . . ? C16 C17 N8 107.8(9) . . ? C16 C17 H17 126.1 . . ? N8 C17 H17 126.1 . . ? N10 C18 C32 121.7(10) . . ? N10 C18 N8 116.0(8) . . ? C32 C18 N8 122.2(9) . . ? C34 C20 N10 123.2(12) . . ? C34 C20 H20 118.4 . . ? N10 C20 H20 118.4 . . ? C22 C21 N6 106.3(8) . . ? C22 C21 H21 126.9 . . ? N6 C21 H21 126.9 . . ? C21 C22 N5 108.6(9) . . ? C21 C22 H22 125.7 . . ? N5 C22 H22 125.7 . . ? C35 C23 C9 119.2(10) . . ? C35 C23 H23 120.4 . . ? C9 C23 H23 120.4 . . ? C26 C25 N9 123.8(9) . . ? C26 C25 N5 120.4(9) . . ? N9 C25 N5 115.8(9) . . ? C25 C26 C31 117.1(11) . . ? C25 C26 H26 121.4 . . ? C31 C26 H26 121.4 . . ? N9 C27 C28 123.0(12) . . ? N9 C27 H27 118.5 . . ? C28 C27 H27 118.5 . . ? C31 C28 C27 117.9(10) . . ? C31 C28 H28 121.0 . . ? C27 C28 H28 121.0 . . ? C2 C29 H29A 109.5 . . ? C2 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C2 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C1 C30 H30A 109.5 . . ? C1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 C26 120.3(12) . . ? C28 C31 H31 119.8 . . ? C26 C31 H31 119.8 . . ? C33 C32 C18 119.3(12) . . ? C33 C32 H32 120.3 . . ? C18 C32 H32 120.3 . . ? C32 C33 C34 120.6(13) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C20 C34 C33 117.7(12) . . ? C20 C34 H34 121.2 . . ? C33 C34 H34 121.2 . . ? C23 C35 C36 118.1(11) . . ? C23 C35 H35 120.9 . . ? C36 C35 H35 120.9 . . ? C37 C36 C35 122.4(11) . . ? C37 C36 H36 118.8 . . ? C35 C36 H36 118.8 . . ? C36 C37 N4 120.6(11) . . ? C36 C37 H37 119.7 . . ? N4 C37 H37 119.7 . . ? C7 Fe1 C5 88.1(3) . . ? C7 Fe1 N1 92.2(3) . . ? C5 Fe1 N1 172.8(3) . . ? C7 Fe1 N2 173.7(3) . . ? C5 Fe1 N2 92.6(3) . . ? N1 Fe1 N2 87.9(3) . . ? C7 Fe1 N3 97.6(3) . . ? C5 Fe1 N3 81.2(3) . . ? N1 Fe1 N3 91.6(3) . . ? N2 Fe1 N3 88.7(3) . . ? C7 Fe1 N4 81.4(3) . . ? C5 Fe1 N4 99.4(3) . . ? N1 Fe1 N4 87.7(3) . . ? N2 Fe1 N4 92.3(3) . . ? N3 Fe1 N4 178.8(3) . . ? C1 N1 Fe1 176.5(8) . . ? C2 N2 Fe1 176.3(7) . . ? C14 N3 C3 115.2(7) . . ? C14 N3 Fe1 129.9(6) . . ? C3 N3 Fe1 114.9(5) . . ? C37 N4 C9 117.2(8) . . ? C37 N4 Fe1 128.8(7) . . ? C9 N4 Fe1 113.8(6) . . ? C7 N5 C22 110.3(8) . . ? C7 N5 C25 128.1(7) . . ? C22 N5 C25 121.5(7) . . ? C7 N6 C9 118.2(7) . . ? C7 N6 C21 110.6(7) . . ? C9 N6 C21 131.1(7) . . ? C5 N7 C16 112.4(8) . . ? C5 N7 C3 117.8(8) . . ? C16 N7 C3 129.8(8) . . ? C5 N8 C17 111.3(8) . . ? C5 N8 C18 126.7(8) . . ? C17 N8 C18 121.8(9) . . ? C27 N9 C25 117.7(10) . . ? C18 N10 C20 117.2(10) . . ? F10 P1 F10 180.0(10) . 2_665 ? F10 P1 F4 80.3(11) . . ? F10 P1 F4 99.7(11) 2_665 . ? F10 P1 F4 99.7(11) . 2_665 ? F10 P1 F4 80.3(11) 2_665 2_665 ? F4 P1 F4 180.0(13) . 2_665 ? F10 P1 F3 89.2(6) . . ? F10 P1 F3 90.8(6) 2_665 . ? F4 P1 F3 93.5(5) . . ? F4 P1 F3 86.5(5) 2_665 . ? F10 P1 F3 90.8(6) . 2_665 ? F10 P1 F3 89.2(6) 2_665 2_665 ? F4 P1 F3 86.5(5) . 2_665 ? F4 P1 F3 93.5(5) 2_665 2_665 ? F3 P1 F3 180.0(7) . 2_665 ? F12 P2 F12 180.0(19) 2_566 . ? F12 P2 F11 82.4(12) 2_566 2_566 ? F12 P2 F11 97.6(12) . 2_566 ? F12 P2 F11 97.6(12) 2_566 . ? F12 P2 F11 82.4(12) . . ? F11 P2 F11 180.000(9) 2_566 . ? F12 P2 F2 93.8(8) 2_566 . ? F12 P2 F2 86.2(8) . . ? F11 P2 F2 89.9(6) 2_566 . ? F11 P2 F2 90.1(6) . . ? F12 P2 F2 86.2(8) 2_566 2_566 ? F12 P2 F2 93.8(8) . 2_566 ? F11 P2 F2 90.1(6) 2_566 2_566 ? F11 P2 F2 89.9(6) . 2_566 ? F2 P2 F2 180.0(4) . 2_566 ? F6 P3 F5 84.1(12) . . ? F6 P3 F8 90.4(11) . . ? F5 P3 F8 174.4(12) . . ? F6 P3 F7 90.0(9) . . ? F5 P3 F7 87.4(10) . . ? F8 P3 F7 93.3(12) . . ? F6 P3 F9 175.8(9) . . ? F5 P3 F9 97.5(12) . . ? F8 P3 F9 88.1(9) . . ? F7 P3 F9 86.3(8) . . ? F6 P3 F1 99.5(9) . . ? F5 P3 F1 85.5(10) . . ? F8 P3 F1 94.8(10) . . ? F7 P3 F1 167.5(9) . . ? F9 P3 F1 84.5(8) . . ? 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 N3 C3 C12 C13 2.5(15) . . . . ? N7 C3 C12 C13 178.6(8) . . . . ? C3 C12 C13 C15 0.4(15) . . . . ? N3 C14 C15 C13 3.4(15) . . . . ? C12 C13 C15 C14 -3.1(15) . . . . ? N7 C16 C17 N8 2.4(12) . . . . ? N6 C21 C22 N5 4.1(14) . . . . ? N4 C9 C23 C35 -4(2) . . . . ? N6 C9 C23 C35 173.3(13) . . . . ? N9 C25 C26 C31 -4.3(17) . . . . ? N5 C25 C26 C31 175.8(10) . . . . ? N9 C27 C28 C31 1(2) . . . . ? C27 C28 C31 C26 -3(2) . . . . ? C25 C26 C31 C28 4.1(19) . . . . ? N10 C18 C32 C33 -5(3) . . . . ? N8 C18 C32 C33 172.4(16) . . . . ? C18 C32 C33 C34 3(3) . . . . ? N10 C20 C34 C33 -6(4) . . . . ? C32 C33 C34 C20 2(4) . . . . ? C9 C23 C35 C36 4(2) . . . . ? C23 C35 C36 C37 -1(3) . . . . ? C35 C36 C37 N4 -3(3) . . . . ? N5 C7 Fe1 C5 81.0(11) . . . . ? N6 C7 Fe1 C5 -98.5(7) . . . . ? N5 C7 Fe1 N1 -91.8(11) . . . . ? N6 C7 Fe1 N1 88.7(7) . . . . ? N5 C7 Fe1 N2 178(2) . . . . ? N6 C7 Fe1 N2 -2(3) . . . . ? N5 C7 Fe1 N3 0.1(11) . . . . ? N6 C7 Fe1 N3 -179.4(6) . . . . ? N5 C7 Fe1 N4 -179.2(11) . . . . ? N6 C7 Fe1 N4 1.3(7) . . . . ? N8 C5 Fe1 C7 80.2(9) . . . . ? N7 C5 Fe1 C7 -90.8(6) . . . . ? N8 C5 Fe1 N1 173(2) . . . . ? N7 C5 Fe1 N1 2(3) . . . . ? N8 C5 Fe1 N2 -93.5(9) . . . . ? N7 C5 Fe1 N2 95.5(6) . . . . ? N8 C5 Fe1 N3 178.2(10) . . . . ? N7 C5 Fe1 N3 7.2(5) . . . . ? N8 C5 Fe1 N4 -0.8(10) . . . . ? N7 C5 Fe1 N4 -171.7(6) . . . . ? C30 C1 N1 Fe1 -130(18) . . . . ? C7 Fe1 N1 C1 -132(14) . . . . ? C5 Fe1 N1 C1 136(13) . . . . ? N2 Fe1 N1 C1 42(14) . . . . ? N3 Fe1 N1 C1 130(14) . . . . ? N4 Fe1 N1 C1 -51(14) . . . . ? C29 C2 N2 Fe1 -152(24) . . . . ? C7 Fe1 N2 C2 169(11) . . . . ? C5 Fe1 N2 C2 -95(12) . . . . ? N1 Fe1 N2 C2 78(12) . . . . ? N3 Fe1 N2 C2 -14(12) . . . . ? N4 Fe1 N2 C2 165(12) . . . . ? C15 C14 N3 C3 -0.7(13) . . . . ? C15 C14 N3 Fe1 -178.9(7) . . . . ? C12 C3 N3 C14 -2.3(12) . . . . ? N7 C3 N3 C14 -178.9(7) . . . . ? C12 C3 N3 Fe1 176.1(8) . . . . ? N7 C3 N3 Fe1 -0.4(8) . . . . ? C7 Fe1 N3 C14 -98.8(7) . . . . ? C5 Fe1 N3 C14 174.4(7) . . . . ? N1 Fe1 N3 C14 -6.3(7) . . . . ? N2 Fe1 N3 C14 81.5(7) . . . . ? N4 Fe1 N3 C14 -65(15) . . . . ? C7 Fe1 N3 C3 83.1(6) . . . . ? C5 Fe1 N3 C3 -3.8(6) . . . . ? N1 Fe1 N3 C3 175.5(6) . . . . ? N2 Fe1 N3 C3 -96.6(6) . . . . ? N4 Fe1 N3 C3 117(15) . . . . ? C36 C37 N4 C9 3(2) . . . . ? C36 C37 N4 Fe1 -172.4(11) . . . . ? N6 C9 N4 C37 -177.3(10) . . . . ? C23 C9 N4 C37 0.6(17) . . . . ? N6 C9 N4 Fe1 -1.4(11) . . . . ? C23 C9 N4 Fe1 176.6(9) . . . . ? C7 Fe1 N4 C37 175.5(11) . . . . ? C5 Fe1 N4 C37 -98.0(11) . . . . ? N1 Fe1 N4 C37 82.9(11) . . . . ? N2 Fe1 N4 C37 -4.9(11) . . . . ? N3 Fe1 N4 C37 141(15) . . . . ? C7 Fe1 N4 C9 0.1(7) . . . . ? C5 Fe1 N4 C9 86.7(7) . . . . ? N1 Fe1 N4 C9 -92.5(7) . . . . ? N2 Fe1 N4 C9 179.7(7) . . . . ? N3 Fe1 N4 C9 -34(15) . . . . ? N6 C7 N5 C22 2.2(11) . . . . ? Fe1 C7 N5 C22 -177.3(9) . . . . ? N6 C7 N5 C25 -174.0(8) . . . . ? Fe1 C7 N5 C25 6.4(17) . . . . ? C21 C22 N5 C7 -4.2(14) . . . . ? C21 C22 N5 C25 172.4(10) . . . . ? C26 C25 N5 C7 75.2(13) . . . . ? N9 C25 N5 C7 -104.7(11) . . . . ? C26 C25 N5 C22 -100.7(12) . . . . ? N9 C25 N5 C22 79.4(12) . . . . ? N5 C7 N6 C9 177.7(8) . . . . ? Fe1 C7 N6 C9 -2.6(11) . . . . ? N5 C7 N6 C21 0.3(11) . . . . ? Fe1 C7 N6 C21 -180.0(7) . . . . ? N4 C9 N6 C7 2.6(13) . . . . ? C23 C9 N6 C7 -175.3(10) . . . . ? N4 C9 N6 C21 179.4(10) . . . . ? C23 C9 N6 C21 1.5(19) . . . . ? C22 C21 N6 C7 -2.9(13) . . . . ? C22 C21 N6 C9 -179.8(11) . . . . ? N8 C5 N7 C16 -1.1(9) . . . . ? Fe1 C5 N7 C16 173.4(6) . . . . ? N8 C5 N7 C3 175.6(7) . . . . ? Fe1 C5 N7 C3 -10.0(9) . . . . ? C17 C16 N7 C5 -0.9(11) . . . . ? C17 C16 N7 C3 -177.0(9) . . . . ? C12 C3 N7 C5 -169.8(9) . . . . ? N3 C3 N7 C5 6.8(10) . . . . ? C12 C3 N7 C16 6.2(15) . . . . ? N3 C3 N7 C16 -177.3(8) . . . . ? N7 C5 N8 C17 2.6(9) . . . . ? Fe1 C5 N8 C17 -168.9(8) . . . . ? N7 C5 N8 C18 -172.0(8) . . . . ? Fe1 C5 N8 C18 16.5(14) . . . . ? C16 C17 N8 C5 -3.3(12) . . . . ? C16 C17 N8 C18 171.7(9) . . . . ? N10 C18 N8 C5 -132.8(11) . . . . ? C32 C18 N8 C5 49.8(16) . . . . ? N10 C18 N8 C17 53.1(14) . . . . ? C32 C18 N8 C17 -124.4(14) . . . . ? C28 C27 N9 C25 -1(2) . . . . ? C26 C25 N9 C27 2.8(17) . . . . ? N5 C25 N9 C27 -177.3(10) . . . . ? C32 C18 N10 C20 1(2) . . . . ? N8 C18 N10 C20 -176.1(12) . . . . ? C34 C20 N10 C18 4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.231 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.126 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.500 0.500 154.7 -8.8 2 0.479 0.136 0.198 9.6 -0.2 3 0.521 0.864 0.801 9.6 -0.6 #===END