Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Guido Pampaloni' _publ_contact_author_address ; Dipartimento di Chimica e Chimica Industriale Universita di Pisa via Risorginmento 35 Pisa 56126 ITALY ; _publ_contact_author_email PAMPA@DCCI.UNIPI.IT _publ_section_title ; Synthesis, Characterization and Olefin/CO Exchange Reactions of Pyrazolylborato Complexes of Copper(I) ; loop_ _publ_author_name 'Guido Pampaloni' 'Claudia Graiff' 'Riccardo Peloso' 'Antonio Tripicchio' # Attachment 'cif.txt' data_coe _database_code_depnum_ccdc_archive 'CCDC 295829' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19.75 H20 B Cu F12 N4' _chemical_formula_weight 615.75 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 14.289(4) _cell_length_b 9.536(3) _cell_length_c 20.540(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.88(5) _cell_angle_gamma 90.00 _cell_volume 2692.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6211 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.62 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1234 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.719844 _exptl_absorpt_correction_T_max 1.000 _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 'Bruker AXS Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15554 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.62 _reflns_number_total 5945 _reflns_number_gt 3444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART 1000 software' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT SADABS' _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0894P)^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 5945 _refine_ls_number_parameters 376 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1468 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.911 _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 C1 C 0.6825(4) 0.8817(4) 0.7215(2) 0.0812(11) Uani 1 1 d . . . C2 C 0.6773(2) 0.7251(3) 0.71743(15) 0.0589(8) Uani 1 1 d . . . C3 C 0.6453(3) 0.6357(4) 0.75722(16) 0.0660(9) Uani 1 1 d . . . H3 H 0.6195 0.6578 0.7929 0.079 Uiso 1 1 calc R . . C4 C 0.6590(2) 0.5047(4) 0.73370(15) 0.0580(8) Uani 1 1 d . . . C5 C 0.6365(3) 0.3654(4) 0.7581(2) 0.0787(11) Uani 1 1 d . . . C6 C 0.6386(4) 0.8587(5) 0.4789(2) 0.0902(13) Uani 1 1 d . . . C7 C 0.6409(3) 0.7030(3) 0.48888(15) 0.0638(9) Uani 1 1 d . . . C8 C 0.5960(3) 0.6042(4) 0.44253(17) 0.0710(10) Uani 1 1 d . . . H8 H 0.5567 0.6189 0.3988 0.085 Uiso 1 1 calc R . . C9 C 0.6218(2) 0.4800(4) 0.47462(15) 0.0594(8) Uani 1 1 d . . . C10 C 0.5960(3) 0.3357(5) 0.4483(2) 0.0810(11) Uani 1 1 d . . . C11 C 0.8294(3) 0.2288(3) 0.66838(18) 0.0646(9) Uani 1 1 d . . . H11 H 0.7828 0.2038 0.6902 0.077 Uiso 1 1 calc R . . C12 C 0.8087(3) 0.2039(3) 0.60186(17) 0.0615(8) Uani 1 1 d . . . H12 H 0.7473 0.1691 0.5800 0.074 Uiso 1 1 calc R . . C13 C 0.8791(3) 0.2291(4) 0.56055(19) 0.0804(11) Uani 1 1 d . . . H13B H 0.9205 0.3081 0.5793 0.096 Uiso 1 1 calc R . . H13A H 0.8432 0.2528 0.5146 0.096 Uiso 1 1 calc R . . C14 C 0.9421(4) 0.1012(5) 0.5594(3) 0.0995(14) Uani 1 1 d . . . H14A H 0.9930 0.1271 0.5386 0.119 Uiso 1 1 calc R . . H14B H 0.9025 0.0297 0.5312 0.119 Uiso 1 1 calc R . . C15 C 0.9902(4) 0.0375(5) 0.6307(3) 0.1075(16) Uani 1 1 d . . . H15B H 0.9393 0.0001 0.6487 0.129 Uiso 1 1 calc R . . H15A H 1.0314 -0.0402 0.6255 0.129 Uiso 1 1 calc R . . C16 C 1.0498(4) 0.1379(6) 0.6811(3) 0.1116(17) Uani 1 1 d . . . H16A H 1.1113 0.0932 0.7031 0.134 Uiso 1 1 calc R . . H16B H 1.0641 0.2187 0.6567 0.134 Uiso 1 1 calc R . . C17 C 1.0060(4) 0.1878(5) 0.7335(3) 0.1102(16) Uani 1 1 d . . . H17B H 1.0566 0.2315 0.7691 0.132 Uiso 1 1 calc R . . H17A H 0.9825 0.1071 0.7531 0.132 Uiso 1 1 calc R . . C18 C 0.9212(3) 0.2933(4) 0.7102(2) 0.0910(13) Uani 1 1 d . . . H18A H 0.9087 0.3361 0.7498 0.109 Uiso 1 1 calc R . . H18B H 0.9407 0.3670 0.6842 0.109 Uiso 1 1 calc R . . B1 B 0.7579(3) 0.6937(4) 0.61458(17) 0.0567(9) Uani 1 1 d . . . H1A H 0.8220 0.6518 0.6228 0.068 Uiso 1 1 calc R . . H1B H 0.7648 0.7948 0.6134 0.068 Uiso 1 1 calc R . . Cu1 Cu 0.73910(3) 0.38242(4) 0.618300(18) 0.05518(16) Uani 1 1 d . . . F1 F 0.6310(2) 0.9453(2) 0.66737(14) 0.1112(9) Uani 1 1 d . . . F2 F 0.7726(2) 0.9279(3) 0.73542(15) 0.1113(9) Uani 1 1 d . . . F3 F 0.6465(3) 0.9217(3) 0.77284(14) 0.1237(10) Uani 1 1 d . . . F4 F 0.5933(3) 0.2812(3) 0.70878(15) 0.1298(11) Uani 1 1 d . . . F5 F 0.7154(2) 0.2971(3) 0.79219(15) 0.1228(10) Uani 1 1 d . . . F6 F 0.5806(2) 0.3774(3) 0.79878(15) 0.1210(10) Uani 1 1 d . . . F7 F 0.6105(2) 0.9276(2) 0.52521(14) 0.1088(9) Uani 1 1 d . . . F8 F 0.7248(3) 0.9095(3) 0.47906(18) 0.1343(11) Uani 1 1 d . . . F9 F 0.5763(3) 0.8910(3) 0.41987(13) 0.1317(12) Uani 1 1 d . . . F10 F 0.5166(2) 0.3346(3) 0.39932(16) 0.1395(13) Uani 1 1 d . . . F11 F 0.6651(2) 0.2748(3) 0.42890(16) 0.1298(11) Uani 1 1 d . . . F12 F 0.5819(2) 0.2477(3) 0.49539(16) 0.1173(9) Uani 1 1 d . . . N1 N 0.71078(19) 0.6513(2) 0.67160(11) 0.0504(6) Uani 1 1 d . . . N2 N 0.70018(19) 0.5133(2) 0.68208(11) 0.0528(6) Uani 1 1 d . . . N3 N 0.69013(19) 0.6401(2) 0.54581(12) 0.0521(6) Uani 1 1 d . . . N4 N 0.67853(18) 0.4995(3) 0.53704(12) 0.0525(6) Uani 1 1 d . . . C1A C -0.0233(10) 0.4570(13) 0.4634(5) 0.093(4) Uani 0.25 1 d PGDU A -1 C2A C 0.0664(11) 0.3945(10) 0.4922(7) 0.091(5) Uani 0.25 1 d PGDU A -1 H2A H 0.0881 0.3223 0.4696 0.109 Uiso 0.25 1 calc PR A -1 C3A C 0.1237(7) 0.4400(14) 0.5547(8) 0.094(4) Uani 0.25 1 d PGDU A -1 H3A1 H 0.1837 0.3982 0.5739 0.113 Uiso 0.25 1 calc PR A -1 C4A C 0.0912(10) 0.5480(15) 0.5885(5) 0.101(5) Uani 0.25 1 d PGDU A -1 H4A1 H 0.1295 0.5784 0.6303 0.121 Uiso 0.25 1 calc PR A -1 C5A C 0.0015(11) 0.6105(11) 0.5597(7) 0.096(5) Uani 0.25 1 d PGDU A -1 H5A1 H -0.0202 0.6827 0.5823 0.116 Uiso 0.25 1 calc PR A -1 C6A C -0.0557(7) 0.5650(12) 0.4972(7) 0.083(5) Uani 0.25 1 d PGDU A -1 H6A1 H -0.1157 0.6068 0.4780 0.100 Uiso 0.25 1 calc PR A -1 C7A C -0.085(2) 0.411(4) 0.3942(9) 0.223(14) Uani 0.25 1 d PDU A -1 H7A1 H -0.1434 0.4664 0.3815 0.335 Uiso 0.25 1 calc PR A -1 H7A2 H -0.1023 0.3137 0.3959 0.335 Uiso 0.25 1 calc PR A -1 H7A3 H -0.0492 0.4230 0.3614 0.335 Uiso 0.25 1 calc PR A -1 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 0.101(3) 0.066(2) 0.077(3) -0.021(2) 0.026(2) -0.006(2) C2 0.062(2) 0.0629(19) 0.0483(17) -0.0075(14) 0.0090(15) 0.0012(15) C3 0.072(2) 0.080(2) 0.0477(17) -0.0040(16) 0.0197(16) 0.0059(18) C4 0.058(2) 0.069(2) 0.0451(16) 0.0086(14) 0.0109(15) 0.0036(15) C5 0.088(3) 0.086(3) 0.065(2) 0.016(2) 0.026(2) 0.000(2) C6 0.117(4) 0.077(3) 0.070(3) 0.023(2) 0.016(3) 0.000(3) C7 0.077(2) 0.068(2) 0.0445(17) 0.0075(15) 0.0121(16) 0.0027(17) C8 0.079(3) 0.081(2) 0.0457(17) 0.0030(17) 0.0052(17) 0.0098(19) C9 0.054(2) 0.072(2) 0.0471(16) -0.0089(15) 0.0059(15) 0.0034(16) C10 0.074(3) 0.090(3) 0.067(2) -0.032(2) 0.000(2) 0.006(2) C11 0.072(2) 0.0504(17) 0.072(2) 0.0072(15) 0.0213(18) 0.0053(16) C12 0.057(2) 0.0505(18) 0.073(2) -0.0062(15) 0.0109(17) 0.0025(14) C13 0.082(3) 0.086(3) 0.072(2) 0.0054(19) 0.020(2) 0.022(2) C14 0.090(3) 0.103(3) 0.113(4) -0.009(3) 0.040(3) 0.021(3) C15 0.085(3) 0.083(3) 0.150(5) 0.002(3) 0.024(3) 0.032(3) C16 0.070(3) 0.103(4) 0.143(5) 0.009(3) -0.003(3) 0.024(3) C17 0.092(3) 0.110(4) 0.102(3) 0.000(3) -0.018(3) 0.027(3) C18 0.091(3) 0.087(3) 0.076(3) -0.010(2) -0.009(2) 0.014(2) B1 0.056(2) 0.058(2) 0.054(2) -0.0050(16) 0.0126(17) -0.0113(16) Cu1 0.0589(3) 0.0507(2) 0.0535(2) -0.00018(16) 0.01113(17) 0.00369(17) F1 0.158(3) 0.0657(13) 0.1013(18) 0.0073(13) 0.0217(18) 0.0224(15) F2 0.123(2) 0.0804(15) 0.125(2) -0.0299(14) 0.0251(18) -0.0340(15) F3 0.186(3) 0.0836(15) 0.1147(19) -0.0397(15) 0.063(2) 0.0071(17) F4 0.185(3) 0.0858(17) 0.112(2) 0.0174(15) 0.030(2) -0.0481(18) F5 0.126(2) 0.115(2) 0.128(2) 0.0644(18) 0.0362(18) 0.0299(17) F6 0.145(3) 0.117(2) 0.133(2) 0.0404(16) 0.094(2) 0.0136(17) F7 0.153(3) 0.0650(13) 0.1012(18) 0.0085(13) 0.0225(18) 0.0157(15) F8 0.147(3) 0.1032(19) 0.161(3) 0.0360(18) 0.056(2) -0.0313(18) F9 0.186(3) 0.104(2) 0.0804(16) 0.0388(14) -0.0043(19) 0.0191(18) F10 0.111(2) 0.1173(19) 0.137(2) -0.0515(18) -0.055(2) 0.0119(17) F11 0.107(2) 0.135(2) 0.142(2) -0.0780(19) 0.0260(18) 0.0134(17) F12 0.143(2) 0.0750(15) 0.126(2) -0.0227(15) 0.0222(19) -0.0245(15) N1 0.0548(16) 0.0513(14) 0.0412(12) -0.0021(10) 0.0064(11) -0.0032(11) N2 0.0621(17) 0.0506(13) 0.0437(13) 0.0046(10) 0.0113(12) 0.0000(12) N3 0.0564(16) 0.0552(15) 0.0435(13) 0.0017(10) 0.0118(12) -0.0045(11) N4 0.0539(16) 0.0545(14) 0.0459(13) -0.0051(11) 0.0081(12) -0.0005(11) C1A 0.133(11) 0.083(10) 0.085(9) 0.016(7) 0.068(8) -0.055(8) C2A 0.133(13) 0.060(9) 0.129(11) 0.001(9) 0.118(9) -0.008(9) C3A 0.055(8) 0.096(10) 0.152(12) 0.064(8) 0.064(8) -0.002(7) C4A 0.121(12) 0.133(14) 0.059(9) 0.007(8) 0.042(8) -0.071(10) C5A 0.139(13) 0.057(9) 0.140(13) 0.002(9) 0.118(10) -0.014(9) C6A 0.057(9) 0.062(8) 0.155(14) 0.053(8) 0.071(8) 0.005(8) C7A 0.25(3) 0.28(3) 0.128(19) -0.008(17) 0.030(15) -0.19(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 F1 1.303(5) . ? C1 F2 1.316(5) . ? C1 F3 1.349(5) . ? C1 C2 1.497(5) . ? C2 C3 1.344(5) . ? C2 N1 1.362(4) . ? C3 C4 1.372(5) . ? C4 N2 1.348(4) . ? C4 C5 1.486(5) . ? C5 F4 1.307(5) . ? C5 F6 1.310(5) . ? C5 F5 1.324(5) . ? C6 F7 1.307(5) . ? C6 F8 1.323(6) . ? C6 F9 1.330(5) . ? C6 C7 1.498(5) . ? C7 N3 1.331(4) . ? C7 C8 1.368(5) . ? C8 C9 1.356(5) . ? C9 N4 1.329(4) . ? C9 C10 1.488(5) . ? C10 F10 1.294(4) . ? C10 F11 1.299(5) . ? C10 F12 1.337(5) . ? C11 C12 1.338(5) . ? C11 C18 1.490(5) . ? C11 Cu1 2.035(3) . ? C12 C13 1.502(5) . ? C12 Cu1 2.046(3) . ? C13 C14 1.520(5) . ? C14 C15 1.561(7) . ? C15 C16 1.493(7) . ? C16 C17 1.466(7) . ? C17 C18 1.547(6) . ? B1 N1 1.556(4) . ? B1 N3 1.564(4) . ? Cu1 N2 1.995(3) . ? Cu1 N4 1.998(3) . ? N1 N2 1.349(3) . ? N3 N4 1.357(3) . ? C1A C2A 1.3900 . ? C1A C6A 1.3900 . ? C1A C7A 1.521(9) . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C5A C6A 1.3900 . ? 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 F1 C1 F2 108.7(4) . . ? F1 C1 F3 106.7(4) . . ? F2 C1 F3 107.2(3) . . ? F1 C1 C2 114.1(3) . . ? F2 C1 C2 112.2(4) . . ? F3 C1 C2 107.6(3) . . ? C3 C2 N1 109.6(3) . . ? C3 C2 C1 128.2(3) . . ? N1 C2 C1 122.2(3) . . ? C2 C3 C4 104.9(3) . . ? N2 C4 C3 110.9(3) . . ? N2 C4 C5 120.0(3) . . ? C3 C4 C5 129.1(3) . . ? F4 C5 F6 107.8(4) . . ? F4 C5 F5 105.2(4) . . ? F6 C5 F5 106.5(3) . . ? F4 C5 C4 112.8(3) . . ? F6 C5 C4 111.3(3) . . ? F5 C5 C4 112.7(4) . . ? F7 C6 F8 106.6(4) . . ? F7 C6 F9 106.5(4) . . ? F8 C6 F9 107.9(4) . . ? F7 C6 C7 113.5(3) . . ? F8 C6 C7 112.2(4) . . ? F9 C6 C7 109.8(4) . . ? N3 C7 C8 109.6(3) . . ? N3 C7 C6 123.6(3) . . ? C8 C7 C6 126.8(3) . . ? C9 C8 C7 104.5(3) . . ? N4 C9 C8 111.1(3) . . ? N4 C9 C10 120.3(3) . . ? C8 C9 C10 128.6(3) . . ? F10 C10 F11 109.6(3) . . ? F10 C10 F12 106.5(4) . . ? F11 C10 F12 102.7(4) . . ? F10 C10 C9 111.6(4) . . ? F11 C10 C9 113.0(4) . . ? F12 C10 C9 113.0(3) . . ? C12 C11 C18 125.1(4) . . ? C12 C11 Cu1 71.28(19) . . ? C18 C11 Cu1 109.3(2) . . ? C11 C12 C13 123.6(3) . . ? C11 C12 Cu1 70.45(19) . . ? C13 C12 Cu1 113.0(2) . . ? C12 C13 C14 111.8(3) . . ? C13 C14 C15 114.0(4) . . ? C16 C15 C14 114.9(4) . . ? C17 C16 C15 116.1(5) . . ? C16 C17 C18 116.1(4) . . ? C11 C18 C17 113.7(3) . . ? N1 B1 N3 107.8(3) . . ? N2 Cu1 N4 93.67(10) . . ? N2 Cu1 C11 111.74(12) . . ? N4 Cu1 C11 153.43(13) . . ? N2 Cu1 C12 149.80(12) . . ? N4 Cu1 C12 116.51(12) . . ? C11 Cu1 C12 38.27(13) . . ? N2 N1 C2 108.5(2) . . ? N2 N1 B1 117.7(2) . . ? C2 N1 B1 133.8(3) . . ? C4 N2 N1 106.1(2) . . ? C4 N2 Cu1 137.6(2) . . ? N1 N2 Cu1 116.23(18) . . ? C7 N3 N4 108.2(2) . . ? C7 N3 B1 134.0(3) . . ? N4 N3 B1 117.7(2) . . ? C9 N4 N3 106.6(2) . . ? C9 N4 Cu1 137.6(2) . . ? N3 N4 Cu1 115.61(17) . . ? C2A C1A C6A 120.0 . . ? C2A C1A C7A 120.4(14) . . ? C6A C1A C7A 119.6(14) . . ? C3A C2A C1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C4A C5A C6A 120.0 . . ? C5A C6A C1A 120.0 . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.482 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.076 #===END data_van _database_code_depnum_ccdc_archive 'CCDC 295830' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 B Cu F12 N4 O' _chemical_formula_weight 616.69 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' B B 0.0013 0.0007 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.656(2) _cell_length_b 8.994(2) _cell_length_c 12.649(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.750(5) _cell_angle_gamma 90.00 _cell_volume 1177.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5891 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 25.29 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721283 _exptl_absorpt_correction_T_max 1.000 _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 'Bruker AXS Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8087 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.29 _reflns_number_total 3962 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS SMART 1000 software' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT SADABS' _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0958P)^2^+0.7204P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.40(2) _refine_ls_number_reflns 3962 _refine_ls_number_parameters 353 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1602 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 C1 C 0.0438(8) 0.2989(10) 0.8475(6) 0.0656(19) Uani 1 1 d . . . C2 C -0.0115(7) 0.4491(9) 0.8160(6) 0.0544(17) Uani 1 1 d . . . C3 C 0.0383(7) 0.5827(8) 0.8570(6) 0.0554(16) Uani 1 1 d . . . H3 H 0.1142 0.6015 0.9092 0.066 Uiso 1 1 calc R . . C4 C -0.0502(5) 0.6810(11) 0.8029(4) 0.0511(13) Uani 1 1 d . . . C5 C -0.0457(8) 0.8469(9) 0.8130(6) 0.063(2) Uani 1 1 d . . . C6 C -0.1342(8) 0.1778(16) 0.4755(5) 0.078(2) Uani 1 1 d . . . C7 C -0.1909(7) 0.3271(9) 0.4633(6) 0.0578(18) Uani 1 1 d . . . C8 C -0.2241(6) 0.4067(9) 0.3701(6) 0.0563(17) Uani 1 1 d . . . H8 H -0.2145 0.3790 0.3016 0.068 Uiso 1 1 calc R . . C9 C -0.2756(6) 0.5385(9) 0.3983(6) 0.0556(18) Uani 1 1 d . . . C10 C -0.3306(6) 0.6657(12) 0.3318(5) 0.0646(18) Uani 1 1 d . . . C11 C -0.4541(8) 0.8069(11) 0.5617(7) 0.074(2) Uani 1 1 d . . . H11A H -0.5247 0.7437 0.5406 0.088 Uiso 1 1 calc R . . H11B H -0.4150 0.8465 0.5096 0.088 Uiso 1 1 calc R . . C12 C -0.4085(7) 0.8412(9) 0.6676(6) 0.066(2) Uani 1 1 d . . . H12 H -0.3378 0.9047 0.6862 0.079 Uiso 1 1 calc R . . C13 C -0.4647(7) 0.7835(8) 0.7563(6) 0.0568(16) Uani 1 1 d . . . C14 C -0.4488(8) 0.8680(12) 0.8491(7) 0.081(2) Uani 1 1 d . . . H14 H -0.3930 0.9489 0.8575 0.097 Uiso 1 1 calc R . . C15 C -0.5113(9) 0.8389(14) 0.9294(7) 0.091(3) Uani 1 1 d . . . H15 H -0.5019 0.9010 0.9896 0.109 Uiso 1 1 calc R . . C16 C -0.5867(8) 0.7178(13) 0.9187(6) 0.080(3) Uani 1 1 d . . . C17 C -0.6025(8) 0.6258(11) 0.8285(7) 0.078(3) Uani 1 1 d . . . H17 H -0.6547 0.5418 0.8222 0.094 Uiso 1 1 calc R . . C18 C -0.5393(7) 0.6611(11) 0.7476(6) 0.0657(19) Uani 1 1 d . . . H18 H -0.5485 0.5997 0.6871 0.079 Uiso 1 1 calc R . . C19 C -0.6546(11) 0.7879(16) 1.0805(8) 0.100(3) Uani 1 1 d . . . H19A H -0.5716 0.7849 1.1310 0.151 Uiso 1 1 calc R . . H19B H -0.7206 0.7647 1.1180 0.151 Uiso 1 1 calc R . . H19C H -0.6694 0.8855 1.0494 0.151 Uiso 1 1 calc R . . B1 B -0.2181(7) 0.3620(9) 0.6647(6) 0.0491(16) Uani 1 1 d . . . Cu1 Cu -0.29833(7) 0.67902(10) 0.61754(6) 0.0543(3) Uani 1 1 d . . . F1 F -0.0312(6) 0.2203(5) 0.8950(5) 0.0907(15) Uani 1 1 d . . . F2 F 0.0607(5) 0.2187(5) 0.7660(4) 0.0826(15) Uani 1 1 d . . . F3 F 0.1580(5) 0.3140(7) 0.9162(5) 0.1033(19) Uani 1 1 d . . . F4 F -0.0693(7) 0.9153(6) 0.7181(4) 0.1021(18) Uani 1 1 d . . . F5 F -0.1292(6) 0.9013(6) 0.8635(5) 0.1040(18) Uani 1 1 d . . . F6 F 0.0680(6) 0.8930(6) 0.8670(6) 0.110(2) Uani 1 1 d . . . F7 F -0.2141(7) 0.0756(6) 0.5058(5) 0.0993(17) Uani 1 1 d . . . F8 F -0.0249(5) 0.1716(9) 0.5480(4) 0.1045(18) Uani 1 1 d . . . F9 F -0.1182(6) 0.1269(7) 0.3804(4) 0.107(2) Uani 1 1 d . . . F10 F -0.3245(5) 0.6487(8) 0.2312(3) 0.0905(18) Uani 1 1 d . . . F11 F -0.4553(4) 0.6859(9) 0.3297(3) 0.0838(12) Uani 1 1 d . . . F12 F -0.2732(6) 0.7909(6) 0.3672(5) 0.0891(17) Uani 1 1 d . . . N1 N -0.1203(5) 0.4714(6) 0.7399(4) 0.0470(12) Uani 1 1 d . . . N2 N -0.1468(5) 0.6193(6) 0.7313(4) 0.0450(12) Uani 1 1 d . . . N3 N -0.2213(5) 0.4033(6) 0.5432(4) 0.0475(12) Uani 1 1 d . . . N4 N -0.2724(5) 0.5349(6) 0.5065(4) 0.0474(12) Uani 1 1 d . . . O1 O -0.6581(5) 0.6762(12) 0.9919(4) 0.0938(17) Uani 1 1 d . . . H1 H -0.176(5) 0.264(7) 0.678(4) 0.035(14) Uiso 1 1 d . . . H2 H -0.322(6) 0.379(8) 0.681(5) 0.051(17) Uiso 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 0.067(5) 0.063(5) 0.064(4) 0.004(4) 0.013(4) 0.016(4) C2 0.053(4) 0.059(5) 0.053(4) -0.007(3) 0.017(3) -0.001(3) C3 0.062(4) 0.049(4) 0.055(4) 0.001(3) 0.013(3) 0.000(3) C4 0.051(3) 0.054(3) 0.048(3) 0.009(4) 0.012(2) 0.008(4) C5 0.061(5) 0.059(5) 0.066(5) -0.002(4) 0.011(4) 0.006(4) C6 0.080(5) 0.094(6) 0.058(4) -0.009(6) 0.016(4) 0.030(6) C7 0.049(4) 0.060(5) 0.063(4) -0.012(4) 0.011(3) -0.004(3) C8 0.051(3) 0.068(5) 0.050(4) -0.013(3) 0.011(3) -0.008(3) C9 0.041(3) 0.059(5) 0.064(5) -0.004(3) 0.007(3) -0.005(3) C10 0.064(4) 0.077(6) 0.053(3) 0.007(4) 0.013(3) -0.002(5) C11 0.067(5) 0.084(6) 0.073(5) 0.006(4) 0.023(4) 0.040(4) C12 0.060(4) 0.064(5) 0.075(5) 0.005(4) 0.018(4) 0.035(4) C13 0.054(4) 0.053(4) 0.061(4) 0.000(3) 0.008(3) 0.014(3) C14 0.069(5) 0.095(7) 0.081(6) -0.014(5) 0.022(4) 0.003(4) C15 0.077(6) 0.124(9) 0.069(5) -0.025(5) 0.013(5) -0.009(6) C16 0.070(4) 0.122(10) 0.048(4) -0.003(4) 0.012(4) 0.005(5) C17 0.062(4) 0.086(7) 0.085(6) 0.013(4) 0.014(4) 0.017(4) C18 0.073(4) 0.063(5) 0.059(4) -0.003(4) 0.010(3) 0.019(4) C19 0.103(7) 0.134(10) 0.067(5) -0.002(6) 0.026(5) 0.020(7) B1 0.049(4) 0.044(4) 0.052(4) -0.003(3) 0.007(3) -0.001(3) Cu1 0.0481(4) 0.0583(5) 0.0552(4) 0.0014(5) 0.0101(3) 0.0100(4) F1 0.114(4) 0.054(3) 0.107(4) 0.022(2) 0.031(3) 0.009(2) F2 0.079(3) 0.080(4) 0.086(3) -0.009(2) 0.014(2) 0.025(2) F3 0.091(4) 0.095(4) 0.099(4) -0.004(3) -0.028(3) 0.030(3) F4 0.154(5) 0.055(3) 0.087(4) 0.012(3) 0.009(3) -0.015(3) F5 0.121(4) 0.068(3) 0.135(5) -0.022(3) 0.052(4) 0.007(3) F6 0.101(4) 0.060(3) 0.142(5) -0.001(3) -0.027(4) -0.017(3) F7 0.125(4) 0.056(3) 0.112(4) -0.011(3) 0.018(4) -0.005(3) F8 0.085(3) 0.109(4) 0.103(3) -0.026(4) -0.010(3) 0.032(4) F9 0.130(4) 0.108(5) 0.087(3) -0.024(3) 0.031(3) 0.038(3) F10 0.095(3) 0.125(6) 0.054(2) 0.006(3) 0.023(2) -0.009(3) F11 0.060(2) 0.113(4) 0.075(2) 0.022(4) 0.0101(18) 0.016(3) F12 0.102(4) 0.057(3) 0.101(4) 0.012(3) 0.008(3) -0.013(3) N1 0.046(3) 0.044(3) 0.048(3) -0.006(2) 0.006(2) -0.002(2) N2 0.043(2) 0.040(3) 0.048(3) -0.002(2) 0.001(2) -0.001(2) N3 0.039(2) 0.050(3) 0.054(3) -0.007(2) 0.011(2) -0.001(2) N4 0.048(3) 0.051(3) 0.045(3) 0.001(2) 0.015(2) -0.002(2) O1 0.078(3) 0.131(5) 0.073(3) 0.008(5) 0.018(3) -0.010(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 C1 F2 1.305(9) . ? C1 F1 1.314(10) . ? C1 F3 1.324(9) . ? C1 C2 1.489(12) . ? C2 N1 1.335(9) . ? C2 C3 1.365(11) . ? C3 C4 1.353(10) . ? C4 N2 1.321(8) . ? C4 C5 1.497(13) . ? C5 F5 1.309(9) . ? C5 F6 1.309(9) . ? C5 F4 1.319(9) . ? C6 F8 1.301(8) . ? C6 F9 1.335(9) . ? C6 F7 1.368(13) . ? C6 C7 1.466(15) . ? C7 N3 1.324(9) . ? C7 C8 1.352(11) . ? C8 C9 1.388(11) . ? C9 N4 1.362(9) . ? C9 C10 1.457(13) . ? C10 F10 1.299(8) . ? C10 F12 1.309(12) . ? C10 F11 1.336(8) . ? C11 C12 1.348(11) . ? C11 Cu1 2.005(7) . ? C12 C13 1.485(11) . ? C12 Cu1 2.064(7) . ? C13 C18 1.348(12) . ? C13 C14 1.375(12) . ? C14 C15 1.366(13) . ? C15 C16 1.341(15) . ? C16 O1 1.382(10) . ? C16 C17 1.387(13) . ? C17 C18 1.388(12) . ? C19 O1 1.499(14) . ? B1 N3 1.573(9) . ? B1 N1 1.577(9) . ? Cu1 N2 1.965(5) . ? Cu1 N4 1.978(5) . ? N1 N2 1.358(8) . ? N3 N4 1.339(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 C1 F1 106.1(7) . . ? F2 C1 F3 107.3(6) . . ? F1 C1 F3 108.6(7) . . ? F2 C1 C2 114.2(6) . . ? F1 C1 C2 111.4(6) . . ? F3 C1 C2 109.0(7) . . ? N1 C2 C3 109.5(7) . . ? N1 C2 C1 123.4(7) . . ? C3 C2 C1 127.1(7) . . ? C4 C3 C2 102.8(7) . . ? N2 C4 C3 114.1(8) . . ? N2 C4 C5 118.7(6) . . ? C3 C4 C5 127.1(7) . . ? F5 C5 F6 106.2(7) . . ? F5 C5 F4 105.4(7) . . ? F6 C5 F4 106.2(7) . . ? F5 C5 C4 113.8(7) . . ? F6 C5 C4 111.5(6) . . ? F4 C5 C4 113.1(6) . . ? F8 C6 F9 109.6(6) . . ? F8 C6 F7 106.7(8) . . ? F9 C6 F7 104.1(10) . . ? F8 C6 C7 113.0(10) . . ? F9 C6 C7 110.9(8) . . ? F7 C6 C7 112.1(6) . . ? N3 C7 C8 109.3(7) . . ? N3 C7 C6 124.3(7) . . ? C8 C7 C6 126.4(7) . . ? C7 C8 C9 105.5(7) . . ? N4 C9 C8 108.7(7) . . ? N4 C9 C10 120.6(7) . . ? C8 C9 C10 130.7(7) . . ? F10 C10 F12 108.0(7) . . ? F10 C10 F11 106.2(5) . . ? F12 C10 F11 105.7(8) . . ? F10 C10 C9 111.5(8) . . ? F12 C10 C9 112.7(5) . . ? F11 C10 C9 112.3(7) . . ? C12 C11 Cu1 73.0(4) . . ? C11 C12 C13 123.8(9) . . ? C11 C12 Cu1 68.3(4) . . ? C13 C12 Cu1 110.2(5) . . ? C18 C13 C14 118.1(8) . . ? C18 C13 C12 124.1(7) . . ? C14 C13 C12 117.5(8) . . ? C15 C14 C13 123.1(9) . . ? C16 C15 C14 117.8(9) . . ? C15 C16 O1 124.3(9) . . ? C15 C16 C17 121.4(8) . . ? O1 C16 C17 114.3(9) . . ? C18 C17 C16 119.0(9) . . ? C13 C18 C17 120.5(8) . . ? N3 B1 N1 107.4(5) . . ? N2 Cu1 N4 96.4(2) . . ? N2 Cu1 C11 151.9(3) . . ? N4 Cu1 C11 111.7(3) . . ? N2 Cu1 C12 113.4(3) . . ? N4 Cu1 C12 150.0(3) . . ? C11 Cu1 C12 38.7(3) . . ? C2 N1 N2 109.5(5) . . ? C2 N1 B1 132.6(6) . . ? N2 N1 B1 117.9(5) . . ? C4 N2 N1 104.1(6) . . ? C4 N2 Cu1 139.3(5) . . ? N1 N2 Cu1 116.4(4) . . ? C7 N3 N4 110.3(6) . . ? C7 N3 B1 132.2(6) . . ? N4 N3 B1 117.4(5) . . ? N3 N4 C9 106.3(5) . . ? N3 N4 Cu1 116.6(4) . . ? C9 N4 Cu1 136.4(5) . . ? C16 O1 C19 113.6(9) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.809 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.074 #===END data_tevs _database_code_depnum_ccdc_archive 'CCDC 295831' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 B Cu F12 N4 Si' _chemical_formula_weight 624.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.496(2) _cell_length_b 8.5980(10) _cell_length_c 20.795(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.520(10) _cell_angle_gamma 90.00 _cell_volume 2656.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 21 _cell_measurement_theta_max 32 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 2.527 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.797816 _exptl_absorpt_correction_T_max 1.246577 _exptl_absorpt_process_details '(Walker et al., 1983)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ENRAF NONIUS CAD 4' _diffrn_measurement_method 'theta 2 theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 5163 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 70.15 _reflns_number_total 5019 _reflns_number_gt 2631 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1191P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5019 _refine_ls_number_parameters 441 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1897 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.002 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 0.0659(5) 0.9922(9) 0.3862(3) 0.0996(18) Uani 1 1 d . . . C2 C 0.0361(3) 1.0316(6) 0.3128(3) 0.0750(13) Uani 1 1 d . . . C3 C 0.0221(3) 1.1747(7) 0.2835(3) 0.0843(15) Uani 1 1 d . . . H3 H 0.0295 1.2724 0.3048 0.101 Uiso 1 1 calc R . . C4 C -0.0052(3) 1.1439(5) 0.2159(3) 0.0747(13) Uani 1 1 d . C . C5 C -0.0279(5) 1.2552(7) 0.1597(4) 0.0959(18) Uani 1 1 d . . . C6 C 0.2279(4) 0.5838(8) 0.3142(3) 0.0920(16) Uani 1 1 d . . . C7 C 0.1794(3) 0.6299(6) 0.2447(3) 0.0734(13) Uani 1 1 d . . . C8 C 0.2079(3) 0.6126(6) 0.1885(3) 0.0851(15) Uani 1 1 d . . . H8 H 0.2618 0.5672 0.1855 0.102 Uiso 1 1 calc R . . C9 C 0.1409(3) 0.6757(6) 0.1379(3) 0.0713(12) Uani 1 1 d . C . C10 C 0.1363(4) 0.6900(8) 0.0653(3) 0.0898(16) Uani 1 1 d . . . C11 C -0.1144(5) 0.7835(12) 0.0330(4) 0.111(2) Uani 1 1 d D . . C12 C -0.1606(3) 0.8895(7) 0.0589(3) 0.0762(14) Uani 1 1 d D . . C13 C -0.2473(6) 0.6348(11) 0.1172(7) 0.209(6) Uani 1 1 d D . . H13A H -0.2305 0.5804 0.0811 0.250 Uiso 1 1 calc R A 1 H13B H -0.1960 0.6246 0.1574 0.250 Uiso 1 1 calc R A 1 C14A C -0.3245(15) 0.543(3) 0.1306(14) 0.214(16) Uani 0.50 1 d PD B 1 H14A H -0.3813 0.5804 0.1017 0.321 Uiso 0.50 1 calc PR B 1 H14B H -0.3236 0.5555 0.1772 0.321 Uiso 0.50 1 calc PR B 1 H14C H -0.3178 0.4333 0.1216 0.321 Uiso 0.50 1 calc PR B 1 C14B C -0.3117(17) 0.507(2) 0.0826(11) 0.146(8) Uani 0.50 1 d PD B 2 H14D H -0.3045 0.4172 0.1121 0.220 Uiso 0.50 1 calc PR B 2 H14E H -0.2985 0.4769 0.0414 0.220 Uiso 0.50 1 calc PR B 2 H14F H -0.3731 0.5444 0.0723 0.220 Uiso 0.50 1 calc PR B 2 C15 C -0.3604(4) 0.8852(8) 0.0287(4) 0.122(2) Uani 1 1 d D . . H15A H -0.3577 0.8448 -0.0147 0.146 Uiso 1 1 calc R B 1 H15B H -0.4125 0.8398 0.0396 0.146 Uiso 1 1 calc R B 1 C16A C -0.3653(18) 1.0638(10) 0.0279(13) 0.155(12) Uani 0.50 1 d PD B 1 H16A H -0.3991 1.0990 -0.0164 0.232 Uiso 0.50 1 calc PR B 1 H16B H -0.3049 1.1065 0.0391 0.232 Uiso 0.50 1 calc PR B 1 H16C H -0.3950 1.0988 0.0606 0.232 Uiso 0.50 1 calc PR B 1 C16B C -0.377(2) 1.0429(16) -0.0077(11) 0.132(9) Uani 0.50 1 d PD B 2 H16D H -0.3842 1.1229 0.0233 0.198 Uiso 0.50 1 calc PR B 2 H16E H -0.4309 1.0369 -0.0452 0.198 Uiso 0.50 1 calc PR B 2 H16F H -0.3258 1.0683 -0.0240 0.198 Uiso 0.50 1 calc PR B 2 C17 C -0.2468(5) 0.9550(12) 0.1711(4) 0.152(4) Uani 1 1 d D . . H17A H -0.2082 0.8978 0.2093 0.183 Uiso 1 1 calc R B 1 H17B H -0.2168 1.0538 0.1677 0.183 Uiso 1 1 calc R B 1 C18A C -0.3370(13) 0.990(6) 0.1857(16) 0.27(3) Uani 0.50 1 d PD B 1 H18A H -0.3864 0.9567 0.1480 0.406 Uiso 0.50 1 calc PR B 1 H18B H -0.3418 1.1013 0.1924 0.406 Uiso 0.50 1 calc PR B 1 H18C H -0.3395 0.9352 0.2258 0.406 Uiso 0.50 1 calc PR B 1 C18B C -0.3218(15) 0.926(5) 0.2051(16) 0.165(11) Uani 0.50 1 d PD B 2 H18D H -0.3265 1.0145 0.2326 0.248 Uiso 0.50 1 calc PR B 2 H18E H -0.3073 0.8335 0.2331 0.248 Uiso 0.50 1 calc PR B 2 H18F H -0.3786 0.9101 0.1710 0.248 Uiso 0.50 1 calc PR B 2 B1 B 0.0261(4) 0.7381(7) 0.2655(4) 0.0699(14) Uani 1 1 d . . . Cu1 Cu -0.03897(4) 0.84998(8) 0.12500(3) 0.0672(3) Uani 1 1 d . C . F1 F 0.1465(2) 0.9289(5) 0.40561(16) 0.1109(11) Uani 1 1 d . . . F2 F 0.0684(3) 1.1211(5) 0.42221(19) 0.1351(15) Uani 1 1 d . . . F3 F 0.0098(3) 0.8923(5) 0.40440(18) 0.1179(12) Uani 1 1 d . . . F4 F -0.0020(15) 1.2072(19) 0.1077(9) 0.109(5) Uani 0.50 1 d P C 1 F5 F 0.010(2) 1.393(2) 0.1719(13) 0.180(12) Uani 0.50 1 d P C 1 F6 F -0.1142(10) 1.278(3) 0.1338(14) 0.170(10) Uani 0.50 1 d P C 1 F4A F 0.0264(19) 1.243(3) 0.1229(12) 0.184(11) Uani 0.50 1 d P C 2 F5A F -0.0217(15) 1.3945(17) 0.1854(11) 0.125(6) Uani 0.50 1 d P C 2 F6A F -0.1117(14) 1.244(2) 0.1207(13) 0.175(10) Uani 0.50 1 d P C 2 F7 F 0.2406(2) 0.6991(5) 0.35683(18) 0.1128(11) Uani 1 1 d . . . F8 F 0.1840(2) 0.4734(5) 0.3384(2) 0.1208(13) Uani 1 1 d . . . F9 F 0.3085(2) 0.5255(5) 0.3170(2) 0.1206(13) Uani 1 1 d . . . F10 F 0.1015(19) 0.849(3) 0.0448(17) 0.087(4) Uani 0.50 1 d P D 1 F11 F 0.2189(13) 0.695(3) 0.0637(10) 0.112(4) Uani 0.50 1 d P D 1 F12 F 0.089(2) 0.576(3) 0.0328(14) 0.130(9) Uani 0.50 1 d P D 1 F10A F 0.2098(16) 0.647(3) 0.0467(10) 0.134(7) Uani 0.50 1 d P D 2 F11A F 0.115(2) 0.812(3) 0.0396(18) 0.103(6) Uani 0.50 1 d P D 2 F12A F 0.0705(17) 0.610(3) 0.0206(15) 0.105(6) Uani 0.50 1 d P D 2 N1 N 0.0187(2) 0.9200(5) 0.2654(2) 0.0663(9) Uani 1 1 d . C . N2 N -0.0082(2) 0.9908(4) 0.2042(2) 0.0656(9) Uani 1 1 d . . . N3 N 0.0968(2) 0.6956(4) 0.2268(2) 0.0662(10) Uani 1 1 d . C . N4 N 0.0724(2) 0.7249(4) 0.1599(2) 0.0657(9) Uani 1 1 d . . . Si1 Si -0.25573(9) 0.8427(2) 0.09478(8) 0.0854(4) Uani 1 1 d . B . H12 H -0.152(4) 0.996(4) 0.053(3) 0.092(18) Uiso 1 1 d D . . H11B H -0.093(5) 0.842(7) -0.001(3) 0.13(3) Uiso 1 1 d D . . H11A H -0.120(5) 0.676(4) 0.044(3) 0.11(3) Uiso 1 1 d D . . H1 H -0.042(3) 0.690(4) 0.2389(19) 0.055(11) Uiso 1 1 d . . . H2 H 0.054(3) 0.702(6) 0.313(2) 0.075(14) Uiso 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 0.111(5) 0.107(5) 0.083(4) -0.022(4) 0.031(4) 0.000(4) C2 0.069(3) 0.080(3) 0.077(3) -0.014(3) 0.022(2) -0.004(3) C3 0.070(3) 0.080(4) 0.100(4) -0.028(3) 0.019(3) -0.004(3) C4 0.067(3) 0.054(3) 0.100(4) -0.005(3) 0.016(3) -0.003(2) C5 0.099(5) 0.060(3) 0.130(6) -0.003(4) 0.035(4) 0.001(3) C6 0.078(4) 0.083(4) 0.113(5) 0.013(4) 0.024(3) 0.015(3) C7 0.058(2) 0.064(3) 0.098(4) 0.006(3) 0.021(2) 0.003(2) C8 0.059(3) 0.077(3) 0.119(4) -0.004(3) 0.025(3) 0.008(2) C9 0.064(3) 0.067(3) 0.088(3) -0.004(2) 0.030(2) -0.002(2) C10 0.082(4) 0.085(4) 0.105(5) -0.013(4) 0.032(3) -0.001(3) C11 0.081(4) 0.148(8) 0.092(5) -0.038(5) 0.004(3) 0.013(5) C12 0.061(3) 0.091(4) 0.070(3) -0.007(3) 0.008(2) 0.001(3) C13 0.113(7) 0.144(8) 0.325(16) 0.088(9) -0.010(8) -0.014(6) C14A 0.20(3) 0.121(18) 0.24(3) 0.02(2) -0.06(2) -0.033(18) C14B 0.158(17) 0.099(14) 0.17(2) 0.026(14) 0.020(17) -0.023(12) C15 0.068(4) 0.131(6) 0.153(6) 0.008(5) 0.009(4) 0.013(4) C16A 0.078(12) 0.149(18) 0.23(3) 0.090(18) 0.037(19) 0.046(11) C16B 0.108(14) 0.156(18) 0.115(15) 0.049(11) 0.006(12) 0.022(11) C17 0.096(5) 0.240(11) 0.138(6) -0.062(7) 0.060(5) -0.037(6) C18A 0.13(2) 0.54(9) 0.16(3) -0.20(4) 0.077(19) -0.03(3) C18B 0.077(11) 0.27(3) 0.16(2) -0.01(2) 0.049(12) -0.016(14) B1 0.055(3) 0.065(3) 0.090(4) 0.004(3) 0.023(3) -0.002(3) Cu1 0.0589(4) 0.0654(4) 0.0748(4) -0.0067(3) 0.0152(3) 0.0007(3) F1 0.091(2) 0.143(3) 0.089(2) -0.001(2) 0.0104(18) 0.000(2) F2 0.176(4) 0.128(3) 0.096(2) -0.044(2) 0.030(3) 0.008(3) F3 0.113(3) 0.155(3) 0.099(2) 0.002(2) 0.051(2) -0.006(2) F4 0.147(13) 0.079(5) 0.083(6) 0.019(4) 0.006(7) 0.014(6) F5 0.30(3) 0.096(10) 0.143(13) -0.003(9) 0.054(13) -0.105(13) F6 0.082(9) 0.146(16) 0.27(2) 0.086(14) 0.038(12) 0.046(10) F4A 0.19(2) 0.21(2) 0.19(2) 0.079(17) 0.110(18) 0.071(17) F5A 0.201(15) 0.048(6) 0.124(9) 0.008(5) 0.043(9) 0.006(8) F6A 0.178(19) 0.089(8) 0.183(12) 0.046(8) -0.071(12) -0.041(10) F7 0.099(2) 0.119(3) 0.104(2) 0.000(2) 0.0010(19) 0.022(2) F8 0.112(3) 0.109(3) 0.135(3) 0.050(2) 0.025(2) 0.013(2) F9 0.078(2) 0.124(3) 0.148(3) 0.030(2) 0.013(2) 0.034(2) F10 0.113(8) 0.066(9) 0.097(9) 0.002(7) 0.052(6) 0.021(7) F11 0.090(6) 0.163(13) 0.105(10) -0.038(7) 0.064(6) -0.001(7) F12 0.21(2) 0.087(10) 0.090(11) -0.025(10) 0.042(13) -0.031(13) F10A 0.120(10) 0.192(17) 0.101(10) -0.036(8) 0.048(8) 0.054(10) F11A 0.153(14) 0.082(13) 0.090(7) 0.001(9) 0.060(8) 0.036(8) F12A 0.108(7) 0.106(13) 0.097(10) -0.001(7) 0.020(6) -0.003(7) N1 0.057(2) 0.065(2) 0.075(2) -0.007(2) 0.0151(18) 0.0002(18) N2 0.060(2) 0.058(2) 0.076(2) -0.0034(19) 0.0136(18) -0.0007(17) N3 0.057(2) 0.058(2) 0.082(3) 0.0030(19) 0.0177(19) 0.0018(16) N4 0.060(2) 0.055(2) 0.082(3) -0.0073(19) 0.0192(19) -0.0005(17) Si1 0.0609(8) 0.0980(11) 0.0910(10) 0.0011(9) 0.0117(7) -0.0086(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F1 1.316(7) . ? C1 F2 1.331(7) . ? C1 F3 1.350(8) . ? C1 C2 1.502(8) . ? C2 N1 1.347(6) . ? C2 C3 1.363(7) . ? C3 C4 1.374(7) . ? C4 N2 1.337(6) . ? C4 C5 1.475(8) . ? C5 F5A 1.304(19) . ? C5 F4A 1.29(3) . ? C5 F6 1.307(17) . ? C5 F4 1.32(2) . ? C5 F5 1.31(2) . ? C5 F6A 1.325(19) . ? C6 F7 1.307(7) . ? C6 F9 1.332(6) . ? C6 F8 1.346(7) . ? C6 C7 1.480(8) . ? C7 N3 1.351(6) . ? C7 C8 1.369(7) . ? C8 C9 1.362(7) . ? C9 N4 1.338(6) . ? C9 C10 1.496(8) . ? C10 F11 1.292(18) . ? C10 F12 1.29(3) . ? C10 F11A 1.18(3) . ? C10 F10 1.49(3) . ? C10 F12A 1.36(3) . ? C10 F10A 1.35(2) . ? C11 C12 1.361(9) . ? C11 Cu1 2.020(7) . ? C12 Si1 1.875(6) . ? C12 Cu1 2.021(5) . ? C13 C14B 1.523(5) . ? C13 C14A 1.527(5) . ? C13 Si1 1.843(9) . ? C15 C16A 1.538(5) . ? C15 C16B 1.539(5) . ? C15 Si1 1.839(6) . ? C17 C18A 1.543(5) . ? C17 C18B 1.544(5) . ? C17 Si1 1.828(7) . ? B1 N1 1.568(7) . ? B1 N3 1.577(7) . ? Cu1 N4 1.988(4) . ? Cu1 N2 1.990(4) . ? N1 N2 1.365(5) . ? N3 N4 1.356(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C1 F2 107.4(6) . . ? F1 C1 F3 106.4(6) . . ? F2 C1 F3 106.9(5) . . ? F1 C1 C2 113.3(5) . . ? F2 C1 C2 109.5(6) . . ? F3 C1 C2 113.0(5) . . ? N1 C2 C3 110.0(5) . . ? N1 C2 C1 121.5(5) . . ? C3 C2 C1 128.4(5) . . ? C2 C3 C4 104.3(5) . . ? N2 C4 C3 111.2(5) . . ? N2 C4 C5 120.4(5) . . ? C3 C4 C5 128.4(5) . . ? F5A C5 F4A 109.6(16) . . ? F5A C5 F6 88.9(15) . . ? F4A C5 F6 122.0(18) . . ? F5A C5 F4 128.2(12) . . ? F4A C5 F4 24.4(17) . . ? F6 C5 F4 102.8(16) . . ? F5A C5 F5 28.0(17) . . ? F4A C5 F5 81.8(15) . . ? F6 C5 F5 107.3(17) . . ? F4 C5 F5 102.4(14) . . ? F5A C5 F6A 105.4(15) . . ? F4A C5 F6A 108.7(18) . . ? F6 C5 F6A 18(2) . . ? F4 C5 F6A 87.1(16) . . ? F5 C5 F6A 119.6(16) . . ? F5A C5 C4 107.4(10) . . ? F4A C5 C4 111.5(12) . . ? F6 C5 C4 114.1(12) . . ? F4 C5 C4 112.7(8) . . ? F5 C5 C4 116.1(13) . . ? F6A C5 C4 114.1(11) . . ? F7 C6 F9 107.3(5) . . ? F7 C6 F8 106.0(5) . . ? F9 C6 F8 106.6(5) . . ? F7 C6 C7 113.3(5) . . ? F9 C6 C7 110.7(5) . . ? F8 C6 C7 112.6(5) . . ? N3 C7 C8 108.6(5) . . ? N3 C7 C6 124.0(5) . . ? C8 C7 C6 127.3(5) . . ? C9 C8 C7 104.8(5) . . ? N4 C9 C8 111.5(5) . . ? N4 C9 C10 120.2(5) . . ? C8 C9 C10 128.3(5) . . ? F11 C10 F12 115.2(16) . . ? F11 C10 F11A 96(2) . . ? F12 C10 F11A 113(2) . . ? F11 C10 F10 104.0(16) . . ? F12 C10 F10 116.2(18) . . ? F11A C10 F10 12(2) . . ? F11 C10 F12A 123.7(15) . . ? F12 C10 F12A 19(2) . . ? F11A C10 F12A 95(2) . . ? F10 C10 F12A 97.5(18) . . ? F11 C10 F10A 23.1(13) . . ? F12 C10 F10A 92.2(17) . . ? F11A C10 F10A 105.2(19) . . ? F10 C10 F10A 115.6(16) . . ? F12A C10 F10A 101.2(15) . . ? F11 C10 C9 105.4(11) . . ? F12 C10 C9 109.1(16) . . ? F11A C10 C9 117.1(14) . . ? F10 C10 C9 106.0(13) . . ? F12A C10 C9 117.5(14) . . ? F10A C10 C9 117.6(11) . . ? C12 C11 Cu1 70.4(4) . . ? C11 C12 Si1 125.1(6) . . ? C11 C12 Cu1 70.3(3) . . ? Si1 C12 Cu1 112.4(3) . . ? C14B C13 C14A 42.9(11) . . ? C14B C13 Si1 126.3(12) . . ? C14A C13 Si1 123.2(14) . . ? C16A C15 C16B 27.5(15) . . ? C16A C15 Si1 103.7(10) . . ? C16B C15 Si1 122.0(11) . . ? C18A C17 C18B 26(3) . . ? C18A C17 Si1 115.2(14) . . ? C18B C17 Si1 115.4(17) . . ? N1 B1 N3 107.0(4) . . ? N4 Cu1 N2 92.74(15) . . ? N4 Cu1 C11 113.7(3) . . ? N2 Cu1 C11 153.4(3) . . ? N4 Cu1 C12 152.2(2) . . ? N2 Cu1 C12 114.72(19) . . ? C11 Cu1 C12 39.4(3) . . ? C2 N1 N2 108.0(4) . . ? C2 N1 B1 135.3(5) . . ? N2 N1 B1 116.7(4) . . ? C4 N2 N1 106.5(4) . . ? C4 N2 Cu1 137.6(4) . . ? N1 N2 Cu1 116.0(3) . . ? C7 N3 N4 109.1(4) . . ? C7 N3 B1 134.2(5) . . ? N4 N3 B1 116.7(4) . . ? C9 N4 N3 105.9(4) . . ? C9 N4 Cu1 137.5(4) . . ? N3 N4 Cu1 115.8(3) . . ? C17 Si1 C15 112.1(4) . . ? C17 Si1 C13 108.1(6) . . ? C15 Si1 C13 111.4(4) . . ? C17 Si1 C12 110.9(3) . . ? C15 Si1 C12 106.7(3) . . ? C13 Si1 C12 107.5(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 70.15 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.679 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.062 #===END data_fn _database_code_depnum_ccdc_archive 'CCDC 295832' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15.75 H8 B Cu F12 N6' _chemical_formula_weight 583.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 9.182(4) _cell_length_b 15.203(5) _cell_length_c 8.306(4) _cell_angle_alpha 86.821(4) _cell_angle_beta 89.007(4) _cell_angle_gamma 96.839(5) _cell_volume 1149.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 21 _cell_measurement_theta_max 45 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 573 _exptl_absorpt_coefficient_mu 2.427 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.817659 _exptl_absorpt_correction_T_max 1.190346 _exptl_absorpt_process_details '(Walker et al., 1983)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD 4' _diffrn_measurement_method 'teta due teta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 4304 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.87 _diffrn_reflns_theta_max 70.02 _reflns_number_total 4296 _reflns_number_gt 3566 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution SHELXS _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP 3' _computing_publication_material ? _refine_special_details ; the maximum shift/error ratio of 0.299 refers to a calculated torsion of a H of a methyl group of solvent molecule of toluene, found also disordered in two positions. 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^)+(0.1248P)^2^+0.7832P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4296 _refine_ls_number_parameters 375 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1854 _refine_ls_wR_factor_gt 0.1741 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.299 _refine_ls_shift/su_mean 0.006 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 0.2738(5) 0.9026(3) 0.4895(5) 0.0554(9) Uani 1 1 d . . . C2 C 0.1126(4) 0.8819(2) 0.4754(5) 0.0474(8) Uani 1 1 d . . . C3 C 0.0353(5) 0.8809(3) 0.3346(5) 0.0523(9) Uani 1 1 d . . . H3 H 0.0714 0.8961 0.2288 0.063 Uiso 1 1 calc R . . C4 C -0.1065(4) 0.8528(3) 0.3847(4) 0.0482(8) Uani 1 1 d . . . C5 C -0.2367(5) 0.8347(3) 0.2809(5) 0.0593(10) Uani 1 1 d . . . C6 C 0.2325(5) 0.7236(3) 0.9942(5) 0.0564(10) Uani 1 1 d . . . C7 C 0.0745(4) 0.7042(2) 0.9585(5) 0.0457(8) Uani 1 1 d . . . C8 C -0.0173(4) 0.6301(3) 1.0117(5) 0.0518(9) Uani 1 1 d . . . H8 H 0.0048 0.5816 1.0781 0.062 Uiso 1 1 calc R . . C9 C -0.1518(4) 0.6439(2) 0.9434(5) 0.0469(8) Uani 1 1 d . . . C10 C -0.2928(5) 0.5838(3) 0.9604(6) 0.0625(11) Uani 1 1 d . . . C11 C -0.4462(5) 0.6188(3) 0.5400(6) 0.0612(10) Uani 1 1 d . . . C12 C -0.5081(6) 0.5395(3) 0.4684(6) 0.0664(12) Uani 1 1 d . . . C13 C -0.4507(4) 0.9121(2) 0.8683(4) 0.0449(8) Uani 1 1 d . . . C14 C -0.5304(5) 0.9752(3) 0.9452(5) 0.0507(8) Uani 1 1 d . . . B1 B 0.0434(5) 0.8551(3) 0.7881(5) 0.0445(9) Uani 1 1 d . . . Cu1 Cu -0.28136(6) 0.77918(3) 0.70076(6) 0.0452(2) Uani 1 1 d . . . F1 F 0.3363(3) 0.83501(19) 0.5547(4) 0.0698(7) Uani 1 1 d . . . F2 F 0.3130(3) 0.97157(19) 0.5800(4) 0.0770(8) Uani 1 1 d . . . F3 F 0.3369(3) 0.9225(2) 0.3447(3) 0.0780(8) Uani 1 1 d . . . F4 F -0.3621(3) 0.84919(19) 0.3489(3) 0.0677(7) Uani 1 1 d . . . F5 F -0.2554(4) 0.7502(2) 0.2404(4) 0.0883(10) Uani 1 1 d . . . F6 F -0.2198(4) 0.8860(3) 0.1439(4) 0.0948(11) Uani 1 1 d . . . F7 F 0.2650(3) 0.79923(19) 1.0680(3) 0.0715(7) Uani 1 1 d . . . F8 F 0.2720(3) 0.6592(2) 1.0948(4) 0.0821(9) Uani 1 1 d . . . F9 F 0.3195(3) 0.7293(2) 0.8633(4) 0.0725(7) Uani 1 1 d . . . F10 F -0.3109(4) 0.53016(19) 0.8373(4) 0.0844(9) Uani 1 1 d . . . F11 F -0.2939(4) 0.5295(3) 1.0924(4) 0.1047(13) Uani 1 1 d . . . F12 F -0.4089(3) 0.6261(2) 0.9646(5) 0.0916(10) Uani 1 1 d . . . N1 N 0.0189(3) 0.85603(19) 0.6022(4) 0.0413(6) Uani 1 1 d . . . N2 N -0.1187(3) 0.8383(2) 0.5457(4) 0.0430(6) Uani 1 1 d . . . N3 N -0.0016(3) 0.75854(19) 0.8653(3) 0.0419(6) Uani 1 1 d . . . N4 N -0.1423(3) 0.72051(19) 0.8570(4) 0.0443(7) Uani 1 1 d . . . N5 N -0.3949(4) 0.6824(2) 0.5946(4) 0.0551(8) Uani 1 1 d . . . N6 N -0.3903(3) 0.8626(2) 0.8055(4) 0.0466(7) Uani 1 1 d . . . C1S C -0.0216(10) 0.4537(5) 0.5056(10) 0.0218(19) Uani 0.25 1 d PGDU A -1 C2S C -0.0924(10) 0.5205(7) 0.4320(11) 0.039(4) Uani 0.25 1 d PGDU A -1 H2S H -0.1759 0.5060 0.3705 0.046 Uiso 0.25 1 calc PR A -1 C3S C -0.0397(13) 0.6090(6) 0.4494(13) 0.062(4) Uani 0.25 1 d PGDU A -1 H3S H -0.0876 0.6542 0.3996 0.074 Uiso 0.25 1 calc PR A -1 C4S C 0.0837(13) 0.6306(5) 0.5404(14) 0.052(5) Uani 0.25 1 d PGDU A -1 H4S H 0.1194 0.6904 0.5521 0.063 Uiso 0.25 1 calc PR A -1 C5S C 0.1545(10) 0.5637(6) 0.6139(12) 0.042(3) Uani 0.25 1 d PGDU A -1 H5S H 0.2380 0.5783 0.6754 0.050 Uiso 0.25 1 calc PR A -1 C6S C 0.1018(9) 0.4752(5) 0.5965(10) 0.027(3) Uani 0.25 1 d PGDU A -1 H6S H 0.1497 0.4300 0.6463 0.032 Uiso 0.25 1 calc PR A -1 C7S C -0.073(3) 0.3598(12) 0.495(3) 0.064(6) Uani 0.25 1 d PDU A -1 H7S1 H -0.0639 0.3287 0.5984 0.096 Uiso 0.25 1 calc PR A -1 H7S2 H -0.0147 0.3351 0.4140 0.096 Uiso 0.25 1 calc PR A -1 H7S3 H -0.1752 0.3530 0.4642 0.096 Uiso 0.25 1 calc PR A -1 H1B H 0.176(4) 0.872(3) 0.807(5) 0.047(10) Uiso 1 1 d . . . H2B H -0.040(5) 0.900(3) 0.842(5) 0.049(11) Uiso 1 1 d . . . H14 H -0.647(5) 0.972(3) 0.929(6) 0.065(13) Uiso 1 1 d . . . H12 H -0.541(6) 0.548(4) 0.361(7) 0.076(16) Uiso 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 0.053(2) 0.057(2) 0.054(2) 0.0054(18) 0.0040(17) -0.0009(17) C2 0.049(2) 0.0448(18) 0.0476(19) 0.0037(15) 0.0019(15) 0.0046(15) C3 0.053(2) 0.059(2) 0.0440(19) 0.0033(16) 0.0014(16) 0.0097(17) C4 0.054(2) 0.053(2) 0.0400(18) -0.0045(15) -0.0033(15) 0.0154(16) C5 0.061(2) 0.075(3) 0.046(2) -0.0084(19) -0.0094(18) 0.020(2) C6 0.049(2) 0.056(2) 0.063(2) 0.0067(18) -0.0073(18) 0.0070(17) C7 0.0417(18) 0.0469(18) 0.0482(19) 0.0003(15) -0.0008(15) 0.0064(15) C8 0.056(2) 0.0444(19) 0.054(2) 0.0043(16) -0.0014(17) 0.0053(16) C9 0.048(2) 0.0412(18) 0.050(2) -0.0027(15) -0.0007(15) -0.0009(15) C10 0.058(3) 0.061(2) 0.062(2) 0.010(2) -0.0059(19) -0.014(2) C11 0.067(3) 0.055(2) 0.061(2) -0.0108(19) -0.009(2) -0.001(2) C12 0.074(3) 0.055(2) 0.069(3) -0.018(2) -0.016(2) -0.006(2) C13 0.0475(19) 0.0447(18) 0.0421(18) -0.0054(14) -0.0021(15) 0.0030(15) C14 0.053(2) 0.050(2) 0.051(2) -0.0103(16) -0.0021(16) 0.0095(16) B1 0.051(2) 0.0386(19) 0.042(2) -0.0012(15) -0.0037(16) -0.0011(16) Cu1 0.0435(3) 0.0422(3) 0.0505(3) -0.0097(2) -0.0013(2) 0.0042(2) F1 0.0484(13) 0.0738(16) 0.0852(18) 0.0110(14) -0.0023(12) 0.0063(11) F2 0.0706(17) 0.0661(16) 0.089(2) -0.0088(14) -0.0003(14) -0.0174(13) F3 0.0626(16) 0.099(2) 0.0652(16) 0.0136(15) 0.0156(13) -0.0108(14) F4 0.0534(14) 0.0849(18) 0.0683(16) -0.0149(13) -0.0088(11) 0.0168(12) F5 0.093(2) 0.095(2) 0.087(2) -0.0482(18) -0.0339(17) 0.0296(18) F6 0.081(2) 0.145(3) 0.0557(15) 0.0237(18) -0.0168(14) 0.015(2) F7 0.0655(16) 0.0730(17) 0.0747(17) -0.0117(13) -0.0215(13) -0.0026(13) F8 0.0656(16) 0.0808(19) 0.098(2) 0.0274(16) -0.0199(15) 0.0128(14) F9 0.0456(13) 0.0913(19) 0.0793(18) -0.0002(15) 0.0074(12) 0.0058(12) F10 0.098(2) 0.0589(15) 0.091(2) -0.0052(14) -0.0275(17) -0.0182(15) F11 0.097(2) 0.111(3) 0.087(2) 0.0454(19) -0.0251(18) -0.049(2) F12 0.0491(15) 0.091(2) 0.129(3) -0.001(2) 0.0125(16) -0.0083(14) N1 0.0393(15) 0.0398(14) 0.0437(15) -0.0027(11) 0.0008(12) -0.0003(11) N2 0.0425(15) 0.0444(15) 0.0429(15) -0.0030(12) -0.0030(12) 0.0074(12) N3 0.0416(15) 0.0410(15) 0.0416(15) -0.0030(12) -0.0006(12) -0.0008(12) N4 0.0452(16) 0.0417(15) 0.0447(16) -0.0055(12) -0.0020(12) -0.0016(12) N5 0.060(2) 0.0457(17) 0.0589(19) -0.0138(15) -0.0086(15) -0.0024(14) N6 0.0478(17) 0.0441(16) 0.0482(16) -0.0100(13) 0.0006(13) 0.0041(13) C1S 0.037(5) 0.009(4) 0.020(4) -0.002(3) 0.005(4) 0.004(3) C2S 0.043(9) 0.059(7) 0.019(6) 0.009(6) -0.010(6) 0.031(7) C3S 0.099(11) 0.048(6) 0.046(8) 0.024(6) 0.019(7) 0.052(8) C4S 0.082(11) 0.028(7) 0.044(9) -0.008(6) 0.039(7) -0.001(7) C5S 0.045(7) 0.044(6) 0.033(6) -0.013(5) 0.007(5) -0.013(5) C6S 0.025(7) 0.039(6) 0.018(5) -0.001(5) -0.003(5) 0.014(5) C7S 0.107(18) 0.018(6) 0.062(11) -0.014(7) 0.023(11) -0.016(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F1 1.330(5) . ? C1 F3 1.329(5) . ? C1 F2 1.341(5) . ? C1 C2 1.484(6) . ? C2 N1 1.359(5) . ? C2 C3 1.378(6) . ? C3 C4 1.371(6) . ? C4 N2 1.344(5) . ? C4 C5 1.494(6) . ? C5 F4 1.321(5) . ? C5 F5 1.338(5) . ? C5 F6 1.339(5) . ? C6 F9 1.331(5) . ? C6 F7 1.338(5) . ? C6 F8 1.340(5) . ? C6 C7 1.484(5) . ? C7 N3 1.363(5) . ? C7 C8 1.371(5) . ? C8 C9 1.401(6) . ? C9 N4 1.327(5) . ? C9 C10 1.493(5) . ? C10 F12 1.310(6) . ? C10 F11 1.334(5) . ? C10 F10 1.343(6) . ? C11 N5 1.144(5) . ? C11 C12 1.435(6) . ? C12 C12 1.310(10) 2_466 ? C13 N6 1.131(5) . ? C13 C14 1.443(5) . ? C14 C14 1.305(8) 2_477 ? B1 N1 1.564(5) . ? B1 N3 1.574(5) . ? Cu1 N6 1.939(3) . ? Cu1 N5 1.960(3) . ? Cu1 N2 2.045(3) . ? Cu1 N4 2.076(3) . ? N1 N2 1.357(4) . ? N3 N4 1.355(4) . ? C1S C2S 1.3900 . ? C1S C6S 1.3900 . ? C1S C7S 1.458(15) . ? C2S C3S 1.3900 . ? C3S C4S 1.3900 . ? C4S C5S 1.3900 . ? C5S C6S 1.3900 . ? 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 F1 C1 F3 106.7(4) . . ? F1 C1 F2 106.0(4) . . ? F3 C1 F2 107.0(3) . . ? F1 C1 C2 112.8(3) . . ? F3 C1 C2 110.4(4) . . ? F2 C1 C2 113.5(4) . . ? N1 C2 C3 109.4(3) . . ? N1 C2 C1 124.1(3) . . ? C3 C2 C1 126.5(4) . . ? C4 C3 C2 103.9(3) . . ? N2 C4 C3 112.0(3) . . ? N2 C4 C5 120.8(4) . . ? C3 C4 C5 127.2(4) . . ? F4 C5 F5 106.0(4) . . ? F4 C5 F6 106.8(4) . . ? F5 C5 F6 107.4(4) . . ? F4 C5 C4 114.2(3) . . ? F5 C5 C4 111.6(4) . . ? F6 C5 C4 110.4(4) . . ? F9 C6 F7 106.5(3) . . ? F9 C6 F8 107.8(4) . . ? F7 C6 F8 105.9(4) . . ? F9 C6 C7 113.3(4) . . ? F7 C6 C7 113.5(4) . . ? F8 C6 C7 109.4(3) . . ? N3 C7 C8 109.4(3) . . ? N3 C7 C6 124.3(3) . . ? C8 C7 C6 126.3(4) . . ? C7 C8 C9 103.5(3) . . ? N4 C9 C8 111.5(3) . . ? N4 C9 C10 121.2(4) . . ? C8 C9 C10 127.3(4) . . ? F12 C10 F11 109.0(4) . . ? F12 C10 F10 106.3(4) . . ? F11 C10 F10 105.2(4) . . ? F12 C10 C9 113.5(4) . . ? F11 C10 C9 110.8(4) . . ? F10 C10 C9 111.6(4) . . ? N5 C11 C12 178.6(5) . . ? C12 C12 C11 121.7(6) 2_466 . ? N6 C13 C14 178.6(4) . . ? C14 C14 C13 120.9(5) 2_477 . ? N1 B1 N3 109.5(3) . . ? N6 Cu1 N5 117.31(14) . . ? N6 Cu1 N2 113.73(13) . . ? N5 Cu1 N2 109.05(14) . . ? N6 Cu1 N4 112.39(13) . . ? N5 Cu1 N4 106.48(13) . . ? N2 Cu1 N4 95.53(12) . . ? N2 N1 C2 108.7(3) . . ? N2 N1 B1 119.9(3) . . ? C2 N1 B1 131.0(3) . . ? C4 N2 N1 106.1(3) . . ? C4 N2 Cu1 134.2(3) . . ? N1 N2 Cu1 118.6(2) . . ? N4 N3 C7 108.8(3) . . ? N4 N3 B1 119.6(3) . . ? C7 N3 B1 131.2(3) . . ? C9 N4 N3 106.7(3) . . ? C9 N4 Cu1 134.2(3) . . ? N3 N4 Cu1 118.5(2) . . ? C11 N5 Cu1 170.3(4) . . ? C13 N6 Cu1 178.3(3) . . ? C2S C1S C6S 120.0 . . ? C2S C1S C7S 122.6(13) . . ? C6S C1S C7S 117.4(13) . . ? C3S C2S C1S 120.0 . . ? C2S C3S C4S 120.0 . . ? C5S C4S C3S 120.0 . . ? C6S C5S C4S 120.0 . . ? C5S C6S C1S 120.0 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 70.02 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.761 _refine_diff_density_min -0.782 _refine_diff_density_rms 0.098