# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'A. R. Barron' _publ_contact_author_email ARB@RUF.RICE.EDU _publ_section_title ; Olefin Coordination in Copper(I) Complexes of Bis(2-pyridyl)amine ; loop_ _publ_author_name 'A. R. Barron' 'John J. Allen' # Attachment 'Cu_dpa__olefin_BF4.cif' data_dpa1o _database_code_depnum_ccdc_archive 'CCDC 692443' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-1-octene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-1-octene)copper(i) tetrafluoroborate ; _chemical_melting_point 396 _chemical_formula_moiety 'C18 H25 Cu N3, B F4' _chemical_formula_sum 'C18 H25 B Cu F4 N3' _chemical_formula_weight 433.76 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' 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' 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 'C 2/c' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.770(4) _cell_length_b 10.399(2) _cell_length_c 23.290(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.98(3) _cell_angle_gamma 90.00 _cell_volume 4069.5(14) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1049 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 14.59 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5400 _exptl_absorpt_correction_T_max 0.8595 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 24172 _diffrn_reflns_av_R_equivalents 0.1494 _diffrn_reflns_av_sigmaI/netI 0.1616 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4921 _reflns_number_gt 1475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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. Data was initially solved by direct methods in P21/n. Once all atoms had been located, the cell was manually transformed to C2/c in the .ins file. All subsequent refinement was performed in space group C2/c. ; _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^)+(0.0671P)^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 4921 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2500 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.2017 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.61049(4) 1.16218(7) -0.14515(3) 0.0833(4) Uani 1 1 d . . . N1 N 0.5232(3) 1.4302(4) -0.1678(2) 0.0811(14) Uani 1 1 d . . . H1A H 0.4997 1.5026 -0.1678 0.097 Uiso 1 1 calc R . . N2 N 0.4973(3) 1.2069(5) -0.1788(2) 0.0743(13) Uani 1 1 d . . . N3 N 0.6521(3) 1.3387(4) -0.13773(19) 0.0729(12) Uani 1 1 d . . . C1 C 0.4707(4) 1.3290(6) -0.1836(2) 0.0710(15) Uani 1 1 d . . . C2 C 0.3903(4) 1.3561(6) -0.2044(3) 0.0838(17) Uani 1 1 d . . . H2A H 0.3730 1.4409 -0.2067 0.101 Uiso 1 1 calc R . . C3 C 0.3367(4) 1.2590(8) -0.2216(3) 0.095(2) Uani 1 1 d . . . H3A H 0.2825 1.2772 -0.2362 0.114 Uiso 1 1 calc R . . C4 C 0.3625(5) 1.1334(7) -0.2175(3) 0.0918(19) Uani 1 1 d . . . H4A H 0.3267 1.0654 -0.2289 0.110 Uiso 1 1 calc R . . C5 C 0.4411(5) 1.1132(6) -0.1964(3) 0.0901(19) Uani 1 1 d . . . H5A H 0.4586 1.0284 -0.1936 0.108 Uiso 1 1 calc R . . C6 C 0.6059(4) 1.4433(7) -0.1518(2) 0.0739(16) Uani 1 1 d . . . C7 C 0.6347(4) 1.5656(6) -0.1513(3) 0.0917(19) Uani 1 1 d . . . H7A H 0.6004 1.6357 -0.1615 0.110 Uiso 1 1 calc R . . C8 C 0.7150(5) 1.5819(8) -0.1357(3) 0.106(2) Uani 1 1 d . . . H8A H 0.7362 1.6640 -0.1346 0.127 Uiso 1 1 calc R . . C9 C 0.7643(4) 1.4775(9) -0.1217(3) 0.106(2) Uani 1 1 d . . . H9A H 0.8191 1.4876 -0.1110 0.127 Uiso 1 1 calc R . . C10 C 0.7323(4) 1.3608(8) -0.1235(3) 0.094(2) Uani 1 1 d . . . H10A H 0.7663 1.2903 -0.1145 0.113 Uiso 1 1 calc R . . C11 C 0.6281(4) 0.9724(6) -0.1367(3) 0.103(2) Uani 1 1 d . . . H11A H 0.6071 0.9289 -0.1083 0.123 Uiso 1 1 calc R . . H11B H 0.6207 0.9247 -0.1739 0.123 Uiso 1 1 calc R . . C12 C 0.6999(5) 1.0339(6) -0.1123(3) 0.095(2) Uani 1 1 d . . . H12A H 0.7354 1.0262 -0.1367 0.114 Uiso 1 1 calc R . . C13 C 0.7426(4) 1.0519(7) -0.0454(3) 0.113(2) Uani 1 1 d . . . H13A H 0.7121 1.0108 -0.0228 0.135 Uiso 1 1 calc R . . H13B H 0.7454 1.1431 -0.0361 0.135 Uiso 1 1 calc R . . C14 C 0.8265(6) 0.9967(11) -0.0247(4) 0.188(5) Uani 1 1 d . . . H14A H 0.8576 1.0521 -0.0419 0.226 Uiso 1 1 calc R . . H14B H 0.8470 1.0093 0.0189 0.226 Uiso 1 1 calc R . . C15 C 0.8455(5) 0.8779(9) -0.0344(4) 0.153(3) Uani 1 1 d . . . H15A H 0.8244 0.8643 -0.0779 0.183 Uiso 1 1 calc R . . H15B H 0.8155 0.8220 -0.0164 0.183 Uiso 1 1 calc R . . C16 C 0.9278(7) 0.8278(11) -0.0146(5) 0.216(6) Uani 1 1 d . . . H16A H 0.9593 0.8975 -0.0225 0.259 Uiso 1 1 calc R . . H16B H 0.9426 0.8221 0.0293 0.259 Uiso 1 1 calc R . . C17 C 0.9555(6) 0.7298(11) -0.0297(4) 0.188(4) Uani 1 1 d . . . H17A H 0.9365 0.7330 -0.0737 0.225 Uiso 1 1 calc R . . H17B H 0.9260 0.6606 -0.0190 0.225 Uiso 1 1 calc R . . C18 C 1.0360(5) 0.6784(9) -0.0150(4) 0.160(4) Uani 1 1 d . . . H18A H 1.0631 0.7209 -0.0393 0.240 Uiso 1 1 calc R . . H18B H 1.0335 0.5878 -0.0233 0.240 Uiso 1 1 calc R . . H18C H 1.0645 0.6927 0.0272 0.240 Uiso 1 1 calc R . . B1 B 0.3993(7) 1.7416(9) -0.1851(6) 0.112(3) Uani 1 1 d . . . F1 F 0.4539(3) 1.6740(5) -0.1956(3) 0.215(3) Uani 1 1 d . . . F2 F 0.4290(4) 1.8269(6) -0.1395(3) 0.215(3) Uani 1 1 d . . . F3 F 0.3627(3) 1.8178(4) -0.2323(3) 0.1664(19) Uani 1 1 d . . . F4 F 0.3480(3) 1.6636(4) -0.1720(3) 0.189(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0797(6) 0.0764(6) 0.0933(6) 0.0046(4) 0.0275(4) 0.0101(4) N1 0.070(4) 0.066(3) 0.105(4) -0.004(3) 0.025(3) 0.008(3) N2 0.073(4) 0.073(3) 0.078(3) -0.001(3) 0.026(3) 0.002(3) N3 0.077(4) 0.070(3) 0.069(3) 0.001(2) 0.020(3) 0.012(3) C1 0.074(5) 0.074(4) 0.067(4) -0.001(3) 0.025(3) -0.005(4) C2 0.063(4) 0.090(5) 0.092(4) 0.012(4) 0.016(4) 0.009(4) C3 0.066(5) 0.132(6) 0.085(5) 0.010(4) 0.021(4) 0.000(5) C4 0.084(6) 0.091(6) 0.099(5) -0.004(4) 0.028(4) -0.016(4) C5 0.095(6) 0.079(4) 0.096(5) -0.003(4) 0.031(4) -0.008(4) C6 0.068(4) 0.092(5) 0.064(4) 0.001(3) 0.025(3) 0.001(4) C7 0.096(6) 0.068(5) 0.111(5) -0.004(4) 0.033(4) -0.002(4) C8 0.098(6) 0.101(6) 0.125(6) -0.007(5) 0.047(5) -0.027(5) C9 0.074(5) 0.113(6) 0.135(6) 0.000(5) 0.039(5) -0.007(5) C10 0.066(5) 0.118(6) 0.095(5) 0.000(4) 0.023(4) 0.012(4) C11 0.120(7) 0.077(5) 0.114(6) 0.009(4) 0.041(5) 0.015(4) C12 0.108(6) 0.088(5) 0.096(6) 0.009(4) 0.041(5) 0.035(4) C13 0.127(7) 0.124(6) 0.082(5) 0.016(4) 0.028(5) 0.045(5) C14 0.198(11) 0.226(12) 0.105(7) -0.017(7) 0.000(7) 0.101(9) C15 0.154(9) 0.134(7) 0.149(8) -0.027(6) 0.019(6) 0.056(6) C16 0.188(11) 0.247(13) 0.161(9) -0.041(8) -0.015(7) 0.152(10) C17 0.170(11) 0.238(12) 0.155(9) 0.006(8) 0.053(8) 0.081(10) C18 0.139(8) 0.197(9) 0.147(7) 0.013(6) 0.049(6) 0.057(7) B1 0.112(9) 0.072(6) 0.143(9) 0.013(6) 0.029(7) 0.014(6) F1 0.153(5) 0.148(4) 0.390(9) 0.054(5) 0.152(6) 0.071(4) F2 0.299(8) 0.165(5) 0.145(4) -0.008(4) 0.024(5) -0.027(5) F3 0.134(4) 0.127(4) 0.204(5) 0.034(4) 0.008(4) 0.004(3) F4 0.184(5) 0.120(4) 0.326(8) 0.041(4) 0.170(5) 0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.963(5) . ? Cu1 N3 1.965(5) . ? Cu1 C11 1.997(6) . ? Cu1 C12 2.024(6) . ? N1 C1 1.375(7) . ? N1 C6 1.401(6) . ? N1 H1A 0.8600 . ? N2 C1 1.347(7) . ? N2 C5 1.360(7) . ? N3 C6 1.337(7) . ? N3 C10 1.374(7) . ? C1 C2 1.380(7) . ? C2 C3 1.357(8) . ? C2 H2A 0.9300 . ? C3 C4 1.377(8) . ? C3 H3A 0.9300 . ? C4 C5 1.338(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.370(8) . ? C7 C8 1.364(8) . ? C7 H7A 0.9300 . ? C8 C9 1.365(9) . ? C8 H8A 0.9300 . ? C9 C10 1.335(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.374(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.505(8) . ? C12 H12A 0.9800 . ? C13 C14 1.523(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.319(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.478(12) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.233(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.460(11) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? B1 F1 1.284(10) . ? B1 F4 1.329(10) . ? B1 F3 1.341(10) . ? B1 F2 1.353(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 97.0(2) . . ? N2 Cu1 C11 112.4(3) . . ? N3 Cu1 C11 150.6(3) . . ? N2 Cu1 C12 152.1(3) . . ? N3 Cu1 C12 110.8(3) . . ? C11 Cu1 C12 39.9(2) . . ? C1 N1 C6 135.0(5) . . ? C1 N1 H1A 112.5 . . ? C6 N1 H1A 112.5 . . ? C1 N2 C5 116.6(5) . . ? C1 N2 Cu1 122.8(4) . . ? C5 N2 Cu1 120.5(5) . . ? C6 N3 C10 115.4(5) . . ? C6 N3 Cu1 123.7(4) . . ? C10 N3 Cu1 120.6(5) . . ? N2 C1 N1 120.7(6) . . ? N2 C1 C2 121.1(6) . . ? N1 C1 C2 118.2(6) . . ? C3 C2 C1 119.9(6) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 119.9(6) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 117.4(6) . . ? C5 C4 H4A 121.3 . . ? C3 C4 H4A 121.3 . . ? C4 C5 N2 125.0(6) . . ? C4 C5 H5A 117.5 . . ? N2 C5 H5A 117.5 . . ? N3 C6 C7 123.8(6) . . ? N3 C6 N1 119.6(6) . . ? C7 C6 N1 116.7(6) . . ? C8 C7 C6 118.2(7) . . ? C8 C7 H7A 120.9 . . ? C6 C7 H7A 120.9 . . ? C7 C8 C9 119.9(7) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C10 C9 C8 118.8(7) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C9 C10 N3 123.9(6) . . ? C9 C10 H10A 118.1 . . ? N3 C10 H10A 118.1 . . ? C12 C11 Cu1 71.1(4) . . ? C12 C11 H11A 116.5 . . ? Cu1 C11 H11A 116.5 . . ? C12 C11 H11B 116.5 . . ? Cu1 C11 H11B 116.5 . . ? H11A C11 H11B 113.5 . . ? C11 C12 C13 125.0(7) . . ? C11 C12 Cu1 69.0(4) . . ? C13 C12 Cu1 112.3(4) . . ? C11 C12 H12A 114.1 . . ? C13 C12 H12A 114.1 . . ? Cu1 C12 H12A 114.1 . . ? C12 C13 C14 113.1(6) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 125.3(9) . . ? C15 C14 H14A 106.0 . . ? C13 C14 H14A 106.0 . . ? C15 C14 H14B 106.0 . . ? C13 C14 H14B 106.0 . . ? H14A C14 H14B 106.3 . . ? C14 C15 C16 123.9(10) . . ? C14 C15 H15A 106.3 . . ? C16 C15 H15A 106.3 . . ? C14 C15 H15B 106.3 . . ? C16 C15 H15B 106.3 . . ? H15A C15 H15B 106.4 . . ? C17 C16 C15 130.5(11) . . ? C17 C16 H16A 104.6 . . ? C15 C16 H16A 104.6 . . ? C17 C16 H16B 104.6 . . ? C15 C16 H16B 104.6 . . ? H16A C16 H16B 105.7 . . ? C16 C17 C18 133.5(12) . . ? C16 C17 H17A 103.8 . . ? C18 C17 H17A 103.8 . . ? C16 C17 H17B 103.8 . . ? C18 C17 H17B 103.8 . . ? H17A C17 H17B 105.4 . . ? 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 . . ? F1 B1 F4 109.1(7) . . ? F1 B1 F3 111.3(10) . . ? F4 B1 F3 111.3(9) . . ? F1 B1 F2 112.5(10) . . ? F4 B1 F2 110.0(10) . . ? F3 B1 F2 102.6(7) . . ? 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 N2 C11 C12 5.4(5) . . . . ? N3 Cu1 N2 C1 -7.0(4) . . . . ? C11 Cu1 N2 C1 174.0(4) . . . . ? C12 Cu1 N2 C1 167.5(5) . . . . ? N3 Cu1 N2 C5 175.6(4) . . . . ? C11 Cu1 N2 C5 -3.4(5) . . . . ? C12 Cu1 N2 C5 -9.9(7) . . . . ? N2 Cu1 N3 C6 2.3(5) . . . . ? C11 Cu1 N3 C6 -179.7(5) . . . . ? C12 Cu1 N3 C6 -175.0(4) . . . . ? N2 Cu1 N3 C10 -170.7(4) . . . . ? C11 Cu1 N3 C10 7.3(7) . . . . ? C12 Cu1 N3 C10 12.0(5) . . . . ? C5 N2 C1 N1 -178.9(5) . . . . ? Cu1 N2 C1 N1 3.6(7) . . . . ? C5 N2 C1 C2 1.1(8) . . . . ? Cu1 N2 C1 C2 -176.4(4) . . . . ? C6 N1 C1 N2 8.3(9) . . . . ? C6 N1 C1 C2 -171.8(5) . . . . ? N2 C1 C2 C3 -1.4(9) . . . . ? N1 C1 C2 C3 178.7(5) . . . . ? C1 C2 C3 C4 0.8(9) . . . . ? C2 C3 C4 C5 -0.2(9) . . . . ? C3 C4 C5 N2 0.0(10) . . . . ? C1 N2 C5 C4 -0.4(9) . . . . ? Cu1 N2 C5 C4 177.1(5) . . . . ? C10 N3 C6 C7 -1.2(8) . . . . ? Cu1 N3 C6 C7 -174.5(4) . . . . ? C10 N3 C6 N1 179.1(5) . . . . ? Cu1 N3 C6 N1 5.7(7) . . . . ? C1 N1 C6 N3 -13.5(9) . . . . ? C1 N1 C6 C7 166.7(6) . . . . ? N3 C6 C7 C8 0.0(9) . . . . ? N1 C6 C7 C8 179.8(5) . . . . ? C6 C7 C8 C9 0.7(10) . . . . ? C7 C8 C9 C10 -0.1(11) . . . . ? C8 C9 C10 N3 -1.2(11) . . . . ? C6 N3 C10 C9 1.8(9) . . . . ? Cu1 N3 C10 C9 175.3(5) . . . . ? N2 Cu1 C11 C12 -175.2(4) . . . . ? N3 Cu1 C11 C12 6.9(7) . . . . ? Cu1 C11 C12 C13 103.1(6) . . . . ? N2 Cu1 C12 C11 9.4(7) . . . . ? N3 Cu1 C12 C11 -176.4(4) . . . . ? N2 Cu1 C12 C13 -111.0(6) . . . . ? N3 Cu1 C12 C13 63.1(6) . . . . ? C11 Cu1 C12 C13 -120.5(7) . . . . ? C11 C12 C13 C14 123.2(8) . . . . ? Cu1 C12 C13 C14 -157.6(6) . . . . ? C12 C13 C14 C15 -53.3(13) . . . . ? C13 C14 C15 C16 178.9(9) . . . . ? C14 C15 C16 C17 -164.8(14) . . . . ? C15 C16 C17 C18 175.8(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F1 0.86 1.98 2.800(7) 159.3 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.413 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.068 _exptl_crystal_recrystallization_method 'sat. soln in MeOH cooled to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_dpac2o _database_code_depnum_ccdc_archive 'CCDC 692444' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-cis-2-octene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-cis-2-octene)copper(i) tetrafluoroborate ; _chemical_melting_point 418 _chemical_formula_moiety 'C18 H25 Cu N3, B F4' _chemical_formula_sum 'C18 H25 B Cu F4 N3' _chemical_formula_weight 433.76 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8847(18) _cell_length_b 10.554(2) _cell_length_c 21.729(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.36(3) _cell_angle_gamma 90.00 _cell_volume 2035.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3259 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 18.06 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5544 _exptl_absorpt_correction_T_max 0.6767 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 24020 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4942 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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. Disordered atoms C(15A) through C(18A) and C(15B)-C(18B) were assigned different part numbers and refined with site occupancies of 60:40. Adjacent C-C distances were restrained to 1.54(0.025) angst. (DFIX) and alternating C-C distances, i.e. C(15A)-C(17A), were restrained to 2.60(0.050) angst. (DANG). H atoms for C(18A) and C(18B) were placed in idealized positions for a disordered methyl group (HFIX = 123). ; _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^)+(0.1160P)^2^+0.6599P] 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 0.0072(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4942 _refine_ls_number_parameters 282 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1588 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.2306 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.972 _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 -2.85745(7) 0.76580(6) 0.10369(3) 0.0829(3) Uani 1 1 d . . . N1 N -3.0462(4) 1.0155(3) 0.0804(2) 0.0805(11) Uani 1 1 d . . . H1A H -3.1007 1.0828 0.0783 0.097 Uiso 1 1 calc R . . N2 N -3.0636(5) 0.7921(3) 0.07074(19) 0.0775(11) Uani 1 1 d . . . N3 N -2.8002(5) 0.9469(4) 0.10736(18) 0.0781(11) Uani 1 1 d . . . C1 C -3.1293(5) 0.9063(4) 0.0665(2) 0.0724(12) Uani 1 1 d . . . C2 C -3.2799(5) 0.9212(5) 0.0488(2) 0.0826(14) Uani 1 1 d . . . H2A H -3.3227 1.0016 0.0468 0.099 Uiso 1 1 calc R . . C3 C -3.3638(6) 0.8183(5) 0.0346(3) 0.0904(15) Uani 1 1 d . . . H3A H -3.4646 0.8275 0.0221 0.108 Uiso 1 1 calc R . . C4 C -3.3009(7) 0.7000(5) 0.0384(3) 0.0919(16) Uani 1 1 d . . . H4A H -3.3579 0.6278 0.0298 0.110 Uiso 1 1 calc R . . C5 C -3.1531(7) 0.6919(5) 0.0552(3) 0.0903(15) Uani 1 1 d . . . H5A H -3.1094 0.6118 0.0561 0.108 Uiso 1 1 calc R . . C6 C -2.8994(6) 1.0415(4) 0.0965(2) 0.0740(12) Uani 1 1 d . . . C7 C -2.8577(6) 1.1687(5) 0.1017(2) 0.0854(14) Uani 1 1 d . . . H7A H -2.9289 1.2321 0.0946 0.102 Uiso 1 1 calc R . . C8 C -2.7123(7) 1.1992(6) 0.1171(3) 0.1002(17) Uani 1 1 d . . . H8A H -2.6832 1.2837 0.1199 0.120 Uiso 1 1 calc R . . C9 C -2.6088(7) 1.1047(6) 0.1285(3) 0.1027(18) Uani 1 1 d . . . H9A H -2.5090 1.1234 0.1396 0.123 Uiso 1 1 calc R . . C10 C -2.6572(6) 0.9829(6) 0.1230(3) 0.0954(16) Uani 1 1 d . . . H10A H -2.5865 0.9192 0.1305 0.115 Uiso 1 1 calc R . . C11 C -2.8202(8) 0.5818(6) 0.1257(3) 0.1034(18) Uani 1 1 d . . . H11A H -2.8088 0.5274 0.0896 0.124 Uiso 1 1 calc R . . C12 C -2.6934(8) 0.6514(6) 0.1408(3) 0.1043(18) Uani 1 1 d . B . H12A H -2.6107 0.6364 0.1132 0.125 Uiso 1 1 calc R . . C13 C -2.9281(8) 0.5287(7) 0.1711(3) 0.130(2) Uani 1 1 d . . . H13A H -2.8919 0.4480 0.1857 0.195 Uiso 1 1 calc R . . H13B H -3.0257 0.5183 0.1511 0.195 Uiso 1 1 calc R . . H13C H -2.9352 0.5859 0.2051 0.195 Uiso 1 1 calc R . . C14 C -2.6403(9) 0.6881(8) 0.2056(4) 0.136(3) Uani 1 1 d D . . H14A H -2.7269 0.7119 0.2288 0.164 Uiso 0.60 1 calc PR A 1 H14B H -2.5749 0.7614 0.2036 0.164 Uiso 0.60 1 calc PR A 1 H14C H -2.7141 0.6599 0.2336 0.164 Uiso 0.40 1 d PR A 2 H14D H -2.6346 0.7787 0.2081 0.164 Uiso 0.40 1 d PR A 2 C15A C -2.554(3) 0.579(3) 0.2403(11) 0.217(15) Uani 0.60 1 d PD B 1 H15A H -2.5180 0.6101 0.2803 0.260 Uiso 0.60 1 calc PR B 1 H15B H -2.6237 0.5104 0.2473 0.260 Uiso 0.60 1 calc PR B 1 C16A C -2.426(2) 0.528(2) 0.2086(10) 0.190(8) Uani 0.60 1 d PD B 1 H16A H -2.3714 0.5977 0.1909 0.228 Uiso 0.60 1 calc PR B 1 H16B H -2.4636 0.4751 0.1749 0.228 Uiso 0.60 1 calc PR B 1 C17A C -2.311(2) 0.447(2) 0.2496(14) 0.180(11) Uani 0.60 1 d PD B 1 H17A H -2.2159 0.4439 0.2293 0.216 Uiso 0.60 1 calc PR B 1 H17B H -2.2932 0.4905 0.2886 0.216 Uiso 0.60 1 calc PR B 1 C18A C -2.359(3) 0.3171(18) 0.2621(11) 0.214(12) Uani 0.60 1 d PD B 1 H18A H -2.2841 0.2756 0.2879 0.321 Uiso 0.30 1 calc PR B 1 H18B H -2.3726 0.2717 0.2240 0.321 Uiso 0.30 1 calc PR B 1 H18C H -2.4529 0.3190 0.2827 0.321 Uiso 0.30 1 calc PR B 1 H18D H -2.4556 0.3019 0.2418 0.321 Uiso 0.30 1 calc PR B 1 H18E H -2.3672 0.3058 0.3057 0.321 Uiso 0.30 1 calc PR B 1 H18F H -2.2868 0.2586 0.2470 0.321 Uiso 0.30 1 calc PR B 1 C15B C -2.492(2) 0.624(3) 0.2249(14) 0.151(14) Uani 0.40 1 d PD B 2 H15C H -2.4191 0.6433 0.1944 0.181 Uiso 0.40 1 calc PR B 2 H15D H -2.4561 0.6612 0.2636 0.181 Uiso 0.40 1 calc PR B 2 C16B C -2.500(3) 0.486(2) 0.2325(14) 0.142(9) Uani 0.40 1 d PD B 2 H16C H -2.5417 0.4546 0.1935 0.170 Uiso 0.40 1 calc PR B 2 H16D H -2.5768 0.4723 0.2622 0.170 Uiso 0.40 1 calc PR B 2 C17B C -2.378(3) 0.395(3) 0.2503(16) 0.155(13) Uani 0.40 1 d PD B 2 H17C H -2.4219 0.3329 0.2770 0.186 Uiso 0.40 1 calc PR B 2 H17D H -2.3522 0.3512 0.2131 0.186 Uiso 0.40 1 calc PR B 2 C18B C -2.237(3) 0.436(4) 0.2807(15) 0.222(18) Uani 0.40 1 d PD B 2 H18G H -2.1737 0.3633 0.2888 0.333 Uiso 0.20 1 calc PR B 2 H18H H -2.2570 0.4771 0.3189 0.333 Uiso 0.20 1 calc PR B 2 H18I H -2.1860 0.4938 0.2545 0.333 Uiso 0.20 1 calc PR B 2 H18J H -2.2374 0.5261 0.2860 0.333 Uiso 0.20 1 calc PR B 2 H18K H -2.1541 0.4123 0.2559 0.333 Uiso 0.20 1 calc PR B 2 H18L H -2.2251 0.3956 0.3203 0.333 Uiso 0.20 1 calc PR B 2 B1 B -3.2624(8) 1.3151(6) 0.0545(4) 0.096(2) Uani 1 1 d . . . F1 F -3.3910(5) 1.3764(4) 0.0580(3) 0.175(2) Uani 1 1 d . . . F2 F -3.1423(5) 1.3879(4) 0.0499(3) 0.1658(19) Uani 1 1 d . . . F3 F -3.2392(6) 1.2360(4) 0.1057(2) 0.1529(17) Uani 1 1 d . . . F4 F -3.2661(6) 1.2274(4) 0.0076(2) 0.1431(15) 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 0.0791(5) 0.0671(4) 0.1021(6) 0.0055(3) -0.0030(3) 0.0068(3) N1 0.069(2) 0.053(2) 0.119(3) -0.005(2) -0.006(2) 0.0008(18) N2 0.079(3) 0.050(2) 0.103(3) -0.001(2) -0.001(2) -0.0016(18) N3 0.070(3) 0.073(3) 0.090(3) -0.003(2) -0.002(2) -0.002(2) C1 0.070(3) 0.061(3) 0.086(3) -0.002(2) 0.003(2) -0.003(2) C2 0.076(3) 0.064(3) 0.107(4) -0.002(3) -0.002(3) 0.003(2) C3 0.072(3) 0.080(3) 0.119(4) -0.004(3) -0.007(3) -0.003(3) C4 0.088(4) 0.069(3) 0.118(4) -0.004(3) -0.002(3) -0.015(3) C5 0.095(4) 0.053(3) 0.123(4) -0.003(3) 0.002(3) -0.002(3) C6 0.081(3) 0.058(3) 0.084(3) -0.003(2) 0.007(3) -0.005(2) C7 0.090(4) 0.059(3) 0.108(4) -0.009(3) 0.006(3) -0.005(2) C8 0.090(4) 0.084(4) 0.127(5) -0.015(4) 0.009(3) -0.021(3) C9 0.084(4) 0.101(5) 0.123(5) -0.017(4) -0.004(3) -0.024(3) C10 0.077(4) 0.102(4) 0.106(4) -0.007(3) -0.008(3) -0.002(3) C11 0.123(5) 0.074(4) 0.113(4) 0.016(3) 0.004(4) 0.020(3) C12 0.106(5) 0.090(4) 0.117(5) 0.013(3) 0.004(4) 0.021(4) C13 0.143(6) 0.109(5) 0.137(5) 0.040(4) -0.005(5) -0.007(4) C14 0.145(7) 0.139(6) 0.122(6) 0.020(5) -0.036(5) 0.011(5) C15A 0.21(3) 0.35(4) 0.096(12) 0.012(18) 0.031(16) 0.12(3) C16A 0.156(18) 0.163(17) 0.25(3) 0.047(15) 0.037(15) 0.055(15) C17A 0.125(19) 0.21(2) 0.20(2) 0.050(17) -0.053(15) -0.041(16) C18A 0.31(3) 0.162(18) 0.172(17) 0.049(16) -0.016(19) 0.08(2) C15B 0.072(13) 0.30(4) 0.082(18) -0.002(18) -0.011(12) 0.048(19) C16B 0.108(18) 0.15(2) 0.17(2) 0.036(16) 0.049(15) 0.024(15) C17B 0.13(2) 0.20(4) 0.13(2) 0.00(3) -0.037(19) 0.06(3) C18B 0.15(3) 0.35(6) 0.16(3) -0.02(3) 0.00(2) 0.00(3) B1 0.087(5) 0.050(3) 0.149(6) -0.002(4) -0.017(4) 0.000(3) F1 0.122(3) 0.123(3) 0.277(6) -0.027(4) -0.022(3) 0.041(3) F2 0.134(3) 0.089(3) 0.273(6) -0.002(3) -0.017(3) -0.040(2) F3 0.180(5) 0.128(3) 0.151(4) 0.018(3) 0.009(3) 0.032(3) F4 0.172(4) 0.110(3) 0.148(3) -0.032(2) 0.022(3) -0.032(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.959(4) . ? Cu1 N3 1.979(4) . ? Cu1 C11 2.024(6) . ? Cu1 C12 2.034(6) . ? N1 C6 1.364(6) . ? N1 C1 1.396(5) . ? N1 H1A 0.8600 . ? N2 C1 1.341(6) . ? N2 C5 1.357(6) . ? N3 C6 1.345(6) . ? N3 C10 1.356(6) . ? C1 C2 1.386(6) . ? C2 C3 1.346(7) . ? C2 H2A 0.9300 . ? C3 C4 1.369(8) . ? C3 H3A 0.9300 . ? C4 C5 1.351(7) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.396(7) . ? C7 C8 1.359(7) . ? C7 H7A 0.9300 . ? C8 C9 1.372(8) . ? C8 H8A 0.9300 . ? C9 C10 1.359(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.373(9) . ? C11 C13 1.510(9) . ? C11 H11A 0.9800 . ? C12 C14 1.516(9) . ? C12 H12A 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15B 1.52(2) . ? C14 C15A 1.56(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9597 . ? C14 H14D 0.9599 . ? C15A C16A 1.457(19) . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? C16A C17A 1.57(2) . ? C16A H16A 0.9700 . ? C16A H16B 0.9700 . ? C17A C18A 1.47(2) . ? C17A H17A 0.9700 . ? C17A H17B 0.9700 . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C18A H18D 0.9600 . ? C18A H18E 0.9600 . ? C18A H18F 0.9600 . ? C15B C16B 1.47(2) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? C16B C17B 1.48(2) . ? C16B H16C 0.9700 . ? C16B H16D 0.9700 . ? C17B C18B 1.46(3) . ? C17B H17C 0.9700 . ? C17B H17D 0.9700 . ? C18B H18G 0.9600 . ? C18B H18H 0.9600 . ? C18B H18I 0.9600 . ? C18B H18J 0.9600 . ? C18B H18K 0.9600 . ? C18B H18L 0.9600 . ? B1 F1 1.318(7) . ? B1 F2 1.322(7) . ? B1 F4 1.375(8) . ? B1 F3 1.399(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 N2 Cu1 N3 96.48(16) . . ? N2 Cu1 C11 111.3(2) . . ? N3 Cu1 C11 151.4(3) . . ? N2 Cu1 C12 150.8(2) . . ? N3 Cu1 C12 112.3(2) . . ? C11 Cu1 C12 39.5(2) . . ? C6 N1 C1 135.5(4) . . ? C6 N1 H1A 112.2 . . ? C1 N1 H1A 112.2 . . ? C1 N2 C5 115.7(4) . . ? C1 N2 Cu1 123.4(3) . . ? C5 N2 Cu1 120.7(4) . . ? C6 N3 C10 115.9(5) . . ? C6 N3 Cu1 122.9(3) . . ? C10 N3 Cu1 121.1(4) . . ? N2 C1 C2 122.3(4) . . ? N2 C1 N1 120.2(4) . . ? C2 C1 N1 117.5(4) . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 120.1(5) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 117.7(5) . . ? C5 C4 H4A 121.2 . . ? C3 C4 H4A 121.2 . . ? C4 C5 N2 124.8(5) . . ? C4 C5 H5A 117.6 . . ? N2 C5 H5A 117.6 . . ? N3 C6 N1 120.5(4) . . ? N3 C6 C7 122.0(5) . . ? N1 C6 C7 117.5(5) . . ? C8 C7 C6 119.6(5) . . ? C8 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? C7 C8 C9 119.7(5) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C10 C9 C8 117.7(5) . . ? C10 C9 H9A 121.2 . . ? C8 C9 H9A 121.2 . . ? N3 C10 C9 125.2(6) . . ? N3 C10 H10A 117.4 . . ? C9 C10 H10A 117.4 . . ? C12 C11 C13 125.4(6) . . ? C12 C11 Cu1 70.6(4) . . ? C13 C11 Cu1 114.1(4) . . ? C12 C11 H11A 113.2 . . ? C13 C11 H11A 113.2 . . ? Cu1 C11 H11A 113.2 . . ? C11 C12 C14 125.4(7) . . ? C11 C12 Cu1 69.9(3) . . ? C14 C12 Cu1 114.0(5) . . ? C11 C12 H12A 113.4 . . ? C14 C12 H12A 113.4 . . ? Cu1 C12 H12A 113.4 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15B 112.1(14) . . ? C12 C14 C15A 112.8(14) . . ? C12 C14 H14A 109.0 . . ? C15A C14 H14A 109.0 . . ? C12 C14 H14B 109.0 . . ? C15A C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C12 C14 H14C 108.3 . . ? C15B C14 H14C 107.0 . . ? C12 C14 H14D 108.7 . . ? C15B C14 H14D 112.5 . . ? H14C C14 H14D 108.0 . . ? C16A C15A C14 115.1(18) . . ? C16A C15A H15A 108.5 . . ? C14 C15A H15A 108.5 . . ? C16A C15A H15B 108.5 . . ? C14 C15A H15B 108.5 . . ? H15A C15A H15B 107.5 . . ? C15A C16A C17A 115.6(19) . . ? C15A C16A H16A 108.4 . . ? C17A C16A H16A 108.4 . . ? C15A C16A H16B 108.4 . . ? C17A C16A H16B 108.4 . . ? H16A C16A H16B 107.4 . . ? C18A C17A C16A 115.0(19) . . ? C18A C17A H17A 108.5 . . ? C16A C17A H17A 108.5 . . ? C18A C17A H17B 108.5 . . ? C16A C17A H17B 108.5 . . ? H17A C17A H17B 107.5 . . ? C17A C18A H18A 109.5 . . ? C17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C17A C18A H18D 109.5 . . ? H18A C18A H18D 141.1 . . ? H18B C18A H18D 56.3 . . ? H18C C18A H18D 56.3 . . ? C17A C18A H18E 109.5 . . ? H18A C18A H18E 56.3 . . ? H18B C18A H18E 141.1 . . ? H18C C18A H18E 56.3 . . ? H18D C18A H18E 109.5 . . ? C17A C18A H18F 109.5 . . ? H18A C18A H18F 56.3 . . ? H18B C18A H18F 56.3 . . ? H18C C18A H18F 141.1 . . ? H18D C18A H18F 109.5 . . ? H18E C18A H18F 109.5 . . ? C16B C15B C14 115.4(19) . . ? C16B C15B H15C 108.4 . . ? C14 C15B H15C 108.4 . . ? C16B C15B H15D 108.4 . . ? C14 C15B H15D 108.4 . . ? H15C C15B H15D 107.5 . . ? C15B C16B C17B 129(2) . . ? C15B C16B H16C 104.9 . . ? C17B C16B H16C 104.9 . . ? C15B C16B H16D 104.9 . . ? C17B C16B H16D 104.9 . . ? H16C C16B H16D 105.8 . . ? C18B C17B C16B 122(3) . . ? C18B C17B H17C 106.8 . . ? C16B C17B H17C 106.8 . . ? C18B C17B H17D 106.8 . . ? C16B C17B H17D 106.8 . . ? H17C C17B H17D 106.6 . . ? C17B C18B H18G 109.5 . . ? C17B C18B H18H 109.5 . . ? H18G C18B H18H 109.5 . . ? C17B C18B H18I 109.5 . . ? H18G C18B H18I 109.5 . . ? H18H C18B H18I 109.5 . . ? C17B C18B H18J 109.5 . . ? H18G C18B H18J 141.1 . . ? H18H C18B H18J 56.3 . . ? H18I C18B H18J 56.3 . . ? C17B C18B H18K 109.5 . . ? H18G C18B H18K 56.3 . . ? H18H C18B H18K 141.1 . . ? H18I C18B H18K 56.3 . . ? H18J C18B H18K 109.5 . . ? C17B C18B H18L 109.5 . . ? H18G C18B H18L 56.3 . . ? H18H C18B H18L 56.3 . . ? H18I C18B H18L 141.1 . . ? H18J C18B H18L 109.5 . . ? H18K C18B H18L 109.5 . . ? F1 B1 F2 115.0(5) . . ? F1 B1 F4 112.2(6) . . ? F2 B1 F4 109.3(6) . . ? F1 B1 F3 110.3(7) . . ? F2 B1 F3 108.3(6) . . ? F4 B1 F3 100.7(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 N3 N2 C11 C12 -2.5(4) . . . . ? N3 Cu1 N2 C1 -9.8(4) . . . . ? C11 Cu1 N2 C1 163.4(4) . . . . ? C12 Cu1 N2 C1 160.4(5) . . . . ? N3 Cu1 N2 C5 175.4(4) . . . . ? C11 Cu1 N2 C5 -11.4(5) . . . . ? C12 Cu1 N2 C5 -14.3(7) . . . . ? N2 Cu1 N3 C6 7.7(4) . . . . ? C11 Cu1 N3 C6 -159.0(5) . . . . ? C12 Cu1 N3 C6 -167.2(4) . . . . ? N2 Cu1 N3 C10 -174.2(4) . . . . ? C11 Cu1 N3 C10 19.1(7) . . . . ? C12 Cu1 N3 C10 10.9(5) . . . . ? C5 N2 C1 C2 1.6(7) . . . . ? Cu1 N2 C1 C2 -173.4(4) . . . . ? C5 N2 C1 N1 -178.8(4) . . . . ? Cu1 N2 C1 N1 6.2(6) . . . . ? C6 N1 C1 N2 3.6(9) . . . . ? C6 N1 C1 C2 -176.8(5) . . . . ? N2 C1 C2 C3 -0.8(8) . . . . ? N1 C1 C2 C3 179.5(5) . . . . ? C1 C2 C3 C4 0.9(8) . . . . ? C2 C3 C4 C5 -1.7(8) . . . . ? C3 C4 C5 N2 2.7(9) . . . . ? C1 N2 C5 C4 -2.6(8) . . . . ? Cu1 N2 C5 C4 172.6(4) . . . . ? C10 N3 C6 N1 179.9(4) . . . . ? Cu1 N3 C6 N1 -2.0(6) . . . . ? C10 N3 C6 C7 -0.6(7) . . . . ? Cu1 N3 C6 C7 177.5(4) . . . . ? C1 N1 C6 N3 -5.9(8) . . . . ? C1 N1 C6 C7 174.6(5) . . . . ? N3 C6 C7 C8 1.1(8) . . . . ? N1 C6 C7 C8 -179.5(5) . . . . ? C6 C7 C8 C9 -1.1(9) . . . . ? C7 C8 C9 C10 0.8(9) . . . . ? C6 N3 C10 C9 0.3(8) . . . . ? Cu1 N3 C10 C9 -177.9(5) . . . . ? C8 C9 C10 N3 -0.4(9) . . . . ? N2 Cu1 C11 C12 -177.7(4) . . . . ? N3 Cu1 C11 C12 -12.0(7) . . . . ? N2 Cu1 C11 C13 -56.7(6) . . . . ? N3 Cu1 C11 C13 109.1(6) . . . . ? C12 Cu1 C11 C13 121.0(7) . . . . ? C13 C11 C12 C14 -0.6(10) . . . . ? Cu1 C11 C12 C14 105.7(6) . . . . ? C13 C11 C12 Cu1 -106.3(6) . . . . ? N2 Cu1 C12 C11 4.3(7) . . . . ? N3 Cu1 C12 C11 173.8(4) . . . . ? N2 Cu1 C12 C14 -116.5(6) . . . . ? N3 Cu1 C12 C14 53.1(6) . . . . ? C11 Cu1 C12 C14 -120.8(7) . . . . ? C11 C12 C14 C15B 113.6(13) . . . . ? Cu1 C12 C14 C15B -164.8(12) . . . . ? C11 C12 C14 C15A 80.7(15) . . . . ? Cu1 C12 C14 C15A 162.3(13) . . . . ? C12 C14 C15A C16A 55(3) . . . . ? C15B C14 C15A C16A -40(3) . . . . ? C14 C15A C16A C17A 163(2) . . . . ? C15A C16A C17A C18A 78(4) . . . . ? C12 C14 C15B C16B -67(3) . . . . ? C15A C14 C15B C16B 31(3) . . . . ? C14 C15B C16B C17B 180(3) . . . . ? C15B C16B C17B C18B 18(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F3 0.86 2.13 2.956(6) 160.4 . _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.549 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.063 _exptl_crystal_recrystallization_method 'sat. soln in MeOH cooled to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_dpacsbn _database_code_depnum_ccdc_archive 'CCDC 692445' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-cis-1,2-(diphenyl)ethene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-cis-1,2-(diphenyl)ethene)copper(i) tetrafluoroborate ; _chemical_melting_point 430 _chemical_formula_moiety 'C24 H21 Cu N3, B F4' _chemical_formula_sum 'C24 H21 B Cu F4 N3' _chemical_formula_weight 501.79 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' 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 10.324(2) _cell_length_b 22.671(5) _cell_length_c 10.923(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.92(3) _cell_angle_gamma 90.00 _cell_volume 2279.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1680 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 15.80 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6435 _exptl_absorpt_correction_T_max 0.9420 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 27790 _diffrn_reflns_av_R_equivalents 0.1147 _diffrn_reflns_av_sigmaI/netI 0.1523 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.34 _reflns_number_total 5568 _reflns_number_gt 2098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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^)+(0.0820P)^2^+0.7302P] 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 5568 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2184 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.66498(7) 0.10785(3) 0.00280(7) 0.0694(3) Uani 1 1 d . . . N1 N 0.3343(5) 0.0729(2) -0.1304(5) 0.0763(13) Uani 1 1 d . . . H1A H 0.2416 0.0687 -0.1658 0.092 Uiso 1 1 calc R . . N2 N 0.5205(5) 0.09970(18) -0.1896(4) 0.0665(12) Uani 1 1 d . . . N3 N 0.5432(5) 0.07738(19) 0.0841(5) 0.0684(12) Uani 1 1 d . . . C1 C 0.3816(7) 0.0849(2) -0.2268(6) 0.0696(15) Uani 1 1 d . . . C2 C 0.2791(7) 0.0812(3) -0.3645(6) 0.0837(17) Uani 1 1 d . . . H2A H 0.1837 0.0705 -0.3882 0.100 Uiso 1 1 calc R . . C3 C 0.3205(9) 0.0933(3) -0.4635(7) 0.097(2) Uani 1 1 d . . . H3A H 0.2532 0.0917 -0.5557 0.116 Uiso 1 1 calc R . . C4 C 0.4631(9) 0.1079(3) -0.4262(7) 0.095(2) Uani 1 1 d . . . H4A H 0.4936 0.1163 -0.4924 0.114 Uiso 1 1 calc R . . C5 C 0.5579(7) 0.1098(3) -0.2908(6) 0.0838(17) Uani 1 1 d . . . H5A H 0.6546 0.1186 -0.2664 0.101 Uiso 1 1 calc R . . C6 C 0.4020(7) 0.0662(2) 0.0104(6) 0.0644(14) Uani 1 1 d . . . C7 C 0.3146(7) 0.0480(3) 0.0710(7) 0.0819(17) Uani 1 1 d . . . H7A H 0.2156 0.0417 0.0177 0.098 Uiso 1 1 calc R . . C8 C 0.3779(9) 0.0398(3) 0.2104(8) 0.0871(19) Uani 1 1 d . . . H8A H 0.3219 0.0281 0.2530 0.104 Uiso 1 1 calc R . . C9 C 0.5248(8) 0.0491(3) 0.2870(6) 0.0828(18) Uani 1 1 d . . . H9A H 0.5705 0.0425 0.3813 0.099 Uiso 1 1 calc R . . C10 C 0.6004(7) 0.0681(3) 0.2209(6) 0.0768(16) Uani 1 1 d . . . H10A H 0.6992 0.0752 0.2735 0.092 Uiso 1 1 calc R . . C11 C 0.8528(6) 0.1410(3) 0.0184(6) 0.0717(15) Uani 1 1 d . . . H11A H 0.9082 0.1104 -0.0010 0.086 Uiso 1 1 calc R . . C12 C 0.8618(6) 0.1331(3) 0.1473(6) 0.0718(16) Uani 1 1 d . . . H12A H 0.9222 0.0989 0.1935 0.086 Uiso 1 1 calc R . . C13 C 0.8589(6) 0.1762(3) 0.2483(6) 0.0707(15) Uani 1 1 d . . . C14 C 0.9167(6) 0.1593(3) 0.3849(7) 0.091(2) Uani 1 1 d . . . H14A H 0.9538 0.1214 0.4094 0.110 Uiso 1 1 calc R . . C15 C 0.9209(8) 0.1971(5) 0.4852(7) 0.114(3) Uani 1 1 d . . . H15A H 0.9627 0.1846 0.5761 0.137 Uiso 1 1 calc R . . C16 C 0.8641(8) 0.2530(4) 0.4529(8) 0.097(2) Uani 1 1 d . . . H16A H 0.8659 0.2785 0.5204 0.117 Uiso 1 1 calc R . . C17 C 0.8044(7) 0.2703(3) 0.3170(7) 0.0894(18) Uani 1 1 d . . . H17A H 0.7651 0.3080 0.2929 0.107 Uiso 1 1 calc R . . C18 C 0.8018(6) 0.2332(3) 0.2172(6) 0.0761(16) Uani 1 1 d . . . H18A H 0.7612 0.2463 0.1267 0.091 Uiso 1 1 calc R . . C19 C 0.8460(6) 0.1961(3) -0.0588(5) 0.0659(14) Uani 1 1 d . . . C20 C 0.9661(6) 0.2112(3) -0.0769(6) 0.0838(18) Uani 1 1 d . . . H20A H 1.0493 0.1880 -0.0375 0.101 Uiso 1 1 calc R . . C21 C 0.9638(8) 0.2609(3) -0.1537(7) 0.093(2) Uani 1 1 d . . . H21A H 1.0458 0.2708 -0.1639 0.112 Uiso 1 1 calc R . . C22 C 0.8410(8) 0.2950(3) -0.2140(6) 0.0829(17) Uani 1 1 d . . . H22A H 0.8392 0.3279 -0.2657 0.099 Uiso 1 1 calc R . . C23 C 0.7216(7) 0.2802(3) -0.1977(6) 0.0791(17) Uani 1 1 d . . . H23A H 0.6380 0.3030 -0.2396 0.095 Uiso 1 1 calc R . . C24 C 0.7229(6) 0.2317(3) -0.1195(6) 0.0724(16) Uani 1 1 d . . . H24A H 0.6414 0.2229 -0.1076 0.087 Uiso 1 1 calc R . . B1 B -0.0632(11) 0.0362(5) -0.2867(12) 0.110(3) Uani 1 1 d . . . F1 F 0.0160(6) 0.0853(3) -0.2443(6) 0.186(2) Uani 1 1 d . . . F2 F 0.0195(8) 0.0008(3) -0.3082(9) 0.231(3) Uani 1 1 d . . . F3 F -0.0727(9) 0.0140(5) -0.1800(9) 0.296(5) Uani 1 1 d . . . F4 F -0.1898(6) 0.0455(3) -0.3817(7) 0.218(3) 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 0.0691(5) 0.0708(5) 0.0661(5) -0.0026(4) 0.0287(4) -0.0034(4) N1 0.066(3) 0.086(3) 0.070(3) 0.002(3) 0.025(3) -0.009(3) N2 0.072(3) 0.067(3) 0.065(3) -0.004(2) 0.034(3) -0.004(2) N3 0.075(3) 0.066(3) 0.059(3) 0.000(2) 0.026(3) 0.000(3) C1 0.076(4) 0.057(3) 0.067(4) -0.003(3) 0.025(3) 0.003(3) C2 0.080(4) 0.090(4) 0.066(4) 0.001(3) 0.020(4) 0.000(3) C3 0.101(6) 0.110(5) 0.062(4) 0.003(4) 0.022(4) 0.007(4) C4 0.125(6) 0.100(5) 0.068(4) -0.001(4) 0.051(5) -0.011(5) C5 0.095(5) 0.093(4) 0.066(4) -0.010(3) 0.040(4) -0.003(4) C6 0.075(4) 0.048(3) 0.072(4) -0.003(3) 0.035(4) 0.000(3) C7 0.083(4) 0.075(4) 0.100(5) -0.006(4) 0.053(4) -0.003(3) C8 0.111(6) 0.082(4) 0.094(5) -0.006(4) 0.069(5) -0.008(4) C9 0.108(6) 0.074(4) 0.068(4) 0.001(3) 0.041(4) 0.003(4) C10 0.083(4) 0.080(4) 0.066(4) -0.005(3) 0.031(4) -0.004(3) C11 0.061(4) 0.076(4) 0.071(4) 0.000(3) 0.024(3) 0.007(3) C12 0.051(3) 0.082(4) 0.077(4) 0.012(3) 0.024(3) 0.014(3) C13 0.053(3) 0.087(4) 0.062(4) 0.003(3) 0.018(3) -0.009(3) C14 0.065(4) 0.111(5) 0.075(5) 0.020(4) 0.011(3) 0.004(4) C15 0.105(6) 0.161(8) 0.053(4) -0.017(5) 0.015(4) -0.011(6) C16 0.100(5) 0.103(6) 0.087(6) -0.019(4) 0.042(4) -0.020(4) C17 0.097(5) 0.092(5) 0.092(5) -0.008(4) 0.055(4) -0.020(4) C18 0.082(4) 0.088(5) 0.064(4) 0.002(3) 0.039(3) -0.007(4) C19 0.056(4) 0.081(4) 0.061(3) -0.013(3) 0.027(3) -0.002(3) C20 0.060(4) 0.116(5) 0.081(4) -0.004(4) 0.037(3) 0.003(4) C21 0.090(5) 0.122(6) 0.086(5) 0.001(4) 0.056(4) -0.008(4) C22 0.093(5) 0.088(4) 0.076(4) 0.002(3) 0.046(4) 0.000(4) C23 0.077(4) 0.087(4) 0.068(4) 0.005(3) 0.028(3) 0.009(3) C24 0.053(3) 0.088(4) 0.074(4) -0.007(3) 0.026(3) -0.005(3) B1 0.074(6) 0.136(9) 0.114(8) -0.008(7) 0.038(6) -0.005(6) F1 0.137(4) 0.152(4) 0.206(6) -0.025(4) 0.021(4) -0.022(4) F2 0.249(8) 0.169(5) 0.342(10) 0.005(5) 0.191(8) 0.060(5) F3 0.191(7) 0.498(16) 0.232(8) 0.082(9) 0.125(6) -0.059(8) F4 0.114(4) 0.238(7) 0.199(6) 0.001(5) -0.019(4) -0.006(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.959(5) . ? Cu1 N3 1.964(5) . ? Cu1 C12 2.011(6) . ? Cu1 C11 2.013(5) . ? N1 C1 1.373(7) . ? N1 C6 1.380(7) . ? N1 H1A 0.8600 . ? N2 C1 1.345(7) . ? N2 C5 1.346(7) . ? N3 C6 1.332(7) . ? N3 C10 1.353(7) . ? C1 C2 1.396(8) . ? C2 C3 1.359(8) . ? C2 H2A 0.9300 . ? C3 C4 1.378(9) . ? C3 H3A 0.9300 . ? C4 C5 1.355(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.401(8) . ? C7 C8 1.371(8) . ? C7 H7A 0.9300 . ? C8 C9 1.376(8) . ? C8 H8A 0.9300 . ? C9 C10 1.352(8) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.380(7) . ? C11 C19 1.491(8) . ? C11 H11A 0.9800 . ? C12 C13 1.485(8) . ? C12 H12A 0.9800 . ? C13 C14 1.387(8) . ? C13 C18 1.397(8) . ? C14 C15 1.376(9) . ? C14 H14A 0.9300 . ? C15 C16 1.375(10) . ? C15 H15A 0.9300 . ? C16 C17 1.381(9) . ? C16 H16A 0.9300 . ? C17 C18 1.367(8) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C20 1.385(8) . ? C19 C24 1.393(7) . ? C20 C21 1.398(8) . ? C20 H20A 0.9300 . ? C21 C22 1.372(9) . ? C21 H21A 0.9300 . ? C22 C23 1.365(8) . ? C22 H22A 0.9300 . ? C23 C24 1.389(7) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? B1 F4 1.266(10) . ? B1 F2 1.269(11) . ? B1 F3 1.313(11) . ? B1 F1 1.335(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 96.9(2) . . ? N2 Cu1 C12 151.3(2) . . ? N3 Cu1 C12 111.8(2) . . ? N2 Cu1 C11 111.2(2) . . ? N3 Cu1 C11 151.9(2) . . ? C12 Cu1 C11 40.1(2) . . ? C1 N1 C6 134.4(5) . . ? C1 N1 H1A 112.8 . . ? C6 N1 H1A 112.8 . . ? C1 N2 C5 117.2(5) . . ? C1 N2 Cu1 122.5(4) . . ? C5 N2 Cu1 120.2(4) . . ? C6 N3 C10 116.7(5) . . ? C6 N3 Cu1 122.9(4) . . ? C10 N3 Cu1 120.4(4) . . ? N2 C1 N1 121.2(5) . . ? N2 C1 C2 121.7(6) . . ? N1 C1 C2 117.1(6) . . ? C3 C2 C1 119.2(6) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 118.5(6) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? N2 C5 C4 123.9(6) . . ? N2 C5 H5A 118.1 . . ? C4 C5 H5A 118.1 . . ? N3 C6 N1 121.0(5) . . ? N3 C6 C7 122.3(6) . . ? N1 C6 C7 116.7(6) . . ? C8 C7 C6 118.6(6) . . ? C8 C7 H7A 120.7 . . ? C6 C7 H7A 120.7 . . ? C7 C8 C9 119.7(6) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C10 C9 C8 117.9(6) . . ? C10 C9 H9A 121.1 . . ? C8 C9 H9A 121.1 . . ? C9 C10 N3 124.8(6) . . ? C9 C10 H10A 117.6 . . ? N3 C10 H10A 117.6 . . ? C12 C11 C19 130.5(6) . . ? C12 C11 Cu1 69.8(3) . . ? C19 C11 Cu1 117.9(4) . . ? C12 C11 H11A 110.6 . . ? C19 C11 H11A 110.6 . . ? Cu1 C11 H11A 110.6 . . ? C11 C12 C13 131.1(6) . . ? C11 C12 Cu1 70.0(3) . . ? C13 C12 Cu1 114.7(4) . . ? C11 C12 H12A 111.2 . . ? C13 C12 H12A 111.2 . . ? Cu1 C12 H12A 111.2 . . ? C14 C13 C18 116.5(6) . . ? C14 C13 C12 118.3(6) . . ? C18 C13 C12 125.3(5) . . ? C15 C14 C13 121.9(7) . . ? C15 C14 H14A 119.1 . . ? C13 C14 H14A 119.1 . . ? C16 C15 C14 120.9(7) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C15 C16 C17 118.0(7) . . ? C15 C16 H16A 121.0 . . ? C17 C16 H16A 121.0 . . ? C18 C17 C16 121.4(7) . . ? C18 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C17 C18 C13 121.4(6) . . ? C17 C18 H18A 119.3 . . ? C13 C18 H18A 119.3 . . ? C20 C19 C24 118.1(6) . . ? C20 C19 C11 118.2(5) . . ? C24 C19 C11 123.6(5) . . ? C19 C20 C21 120.8(6) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C22 C21 C20 120.2(6) . . ? C22 C21 H21A 119.9 . . ? C20 C21 H21A 119.9 . . ? C23 C22 C21 119.5(6) . . ? C23 C22 H22A 120.3 . . ? C21 C22 H22A 120.3 . . ? C22 C23 C24 121.1(6) . . ? C22 C23 H23A 119.4 . . ? C24 C23 H23A 119.4 . . ? C23 C24 C19 120.3(5) . . ? C23 C24 H24A 119.9 . . ? C19 C24 H24A 119.9 . . ? F4 B1 F2 119.0(11) . . ? F4 B1 F3 109.1(9) . . ? F2 B1 F3 104.4(11) . . ? F4 B1 F1 112.9(10) . . ? F2 B1 F1 103.5(9) . . ? F3 B1 F1 107.0(10) . . ? 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 N2 C11 C12 -2.6(4) . . . . ? N3 Cu1 N2 C1 7.8(4) . . . . ? C12 Cu1 N2 C1 -168.8(5) . . . . ? C11 Cu1 N2 C1 -172.3(4) . . . . ? N3 Cu1 N2 C5 -173.1(4) . . . . ? C12 Cu1 N2 C5 10.3(7) . . . . ? C11 Cu1 N2 C5 6.8(5) . . . . ? N2 Cu1 N3 C6 -8.5(4) . . . . ? C12 Cu1 N3 C6 169.7(4) . . . . ? C11 Cu1 N3 C6 171.8(4) . . . . ? N2 Cu1 N3 C10 173.1(4) . . . . ? C12 Cu1 N3 C10 -8.7(5) . . . . ? C11 Cu1 N3 C10 -6.6(7) . . . . ? C5 N2 C1 N1 179.0(5) . . . . ? Cu1 N2 C1 N1 -1.9(7) . . . . ? C5 N2 C1 C2 -1.2(8) . . . . ? Cu1 N2 C1 C2 177.9(4) . . . . ? C6 N1 C1 N2 -7.8(9) . . . . ? C6 N1 C1 C2 172.3(6) . . . . ? N2 C1 C2 C3 -0.6(9) . . . . ? N1 C1 C2 C3 179.2(5) . . . . ? C1 C2 C3 C4 1.2(10) . . . . ? C2 C3 C4 C5 -0.1(10) . . . . ? C1 N2 C5 C4 2.4(8) . . . . ? Cu1 N2 C5 C4 -176.7(5) . . . . ? C3 C4 C5 N2 -1.8(10) . . . . ? C10 N3 C6 N1 -178.4(5) . . . . ? Cu1 N3 C6 N1 3.2(7) . . . . ? C10 N3 C6 C7 2.6(7) . . . . ? Cu1 N3 C6 C7 -175.9(4) . . . . ? C1 N1 C6 N3 7.1(9) . . . . ? C1 N1 C6 C7 -173.8(6) . . . . ? N3 C6 C7 C8 -2.0(8) . . . . ? N1 C6 C7 C8 178.9(5) . . . . ? C6 C7 C8 C9 -0.5(9) . . . . ? C7 C8 C9 C10 2.2(9) . . . . ? C8 C9 C10 N3 -1.6(9) . . . . ? C6 N3 C10 C9 -0.8(8) . . . . ? Cu1 N3 C10 C9 177.7(4) . . . . ? N2 Cu1 C11 C12 177.4(3) . . . . ? N3 Cu1 C11 C12 -2.9(6) . . . . ? N2 Cu1 C11 C19 51.3(5) . . . . ? N3 Cu1 C11 C19 -129.0(4) . . . . ? C12 Cu1 C11 C19 -126.1(6) . . . . ? C19 C11 C12 C13 4.2(10) . . . . ? Cu1 C11 C12 C13 -105.8(6) . . . . ? C19 C11 C12 Cu1 110.0(6) . . . . ? N2 Cu1 C12 C11 -5.1(6) . . . . ? N3 Cu1 C12 C11 178.5(3) . . . . ? N2 Cu1 C12 C13 122.0(5) . . . . ? N3 Cu1 C12 C13 -54.4(5) . . . . ? C11 Cu1 C12 C13 127.1(6) . . . . ? C11 C12 C13 C14 -159.0(6) . . . . ? Cu1 C12 C13 C14 116.6(5) . . . . ? C11 C12 C13 C18 21.1(9) . . . . ? Cu1 C12 C13 C18 -63.3(7) . . . . ? C18 C13 C14 C15 -1.4(9) . . . . ? C12 C13 C14 C15 178.7(6) . . . . ? C13 C14 C15 C16 1.6(11) . . . . ? C14 C15 C16 C17 -0.7(11) . . . . ? C15 C16 C17 C18 -0.2(10) . . . . ? C16 C17 C18 C13 0.3(10) . . . . ? C14 C13 C18 C17 0.5(9) . . . . ? C12 C13 C18 C17 -179.6(5) . . . . ? C12 C11 C19 C20 109.2(7) . . . . ? Cu1 C11 C19 C20 -164.3(4) . . . . ? C12 C11 C19 C24 -74.1(8) . . . . ? Cu1 C11 C19 C24 12.4(7) . . . . ? C24 C19 C20 C21 0.2(8) . . . . ? C11 C19 C20 C21 177.1(5) . . . . ? C19 C20 C21 C22 -1.0(9) . . . . ? C20 C21 C22 C23 0.4(10) . . . . ? C21 C22 C23 C24 0.9(9) . . . . ? C22 C23 C24 C19 -1.7(8) . . . . ? C20 C19 C24 C23 1.1(8) . . . . ? C11 C19 C24 C23 -175.6(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F1 0.86 2.12 2.954(7) 163.1 . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.629 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.063 _exptl_crystal_recrystallization_method 'sat. soln in MeOH cooled to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_nbn _database_code_depnum_ccdc_archive 'CCDC 692446' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-norbornylene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-norbornylene)copper(i) tetrafluoroborate ; _chemical_melting_point 442 _chemical_formula_moiety 'C17 H19 Cu N3, B F4' _chemical_formula_sum 'C17 H19 B Cu F4 N3' _chemical_formula_weight 415.70 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' 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' 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 'C 2/c' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.438(4) _cell_length_b 14.935(3) _cell_length_c 14.510(3) _cell_angle_alpha 90.00 _cell_angle_beta 130.56(3) _cell_angle_gamma 90.00 _cell_volume 3529.7(12) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4423 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 21.91 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 1.18 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 1.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3129 _exptl_absorpt_correction_T_max 0.7234 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 20570 _diffrn_reflns_av_R_equivalents 0.0860 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4279 _reflns_number_gt 2401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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^)+(0.0575P)^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 SHELXL _refine_ls_extinction_coef 0.0044(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4279 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1340 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2264 _refine_ls_wR_factor_gt 0.2193 _refine_ls_goodness_of_fit_ref 1.785 _refine_ls_restrained_S_all 1.785 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.37822(4) -0.12804(5) 0.45792(7) 0.0495(3) Uani 1 1 d . . . N1 N 0.3805(3) 0.0746(3) 0.5216(4) 0.0502(12) Uani 1 1 d . . . H1A H 0.3810 0.1300 0.5384 0.060 Uiso 1 1 calc R . . N2 N 0.2886(3) -0.0430(3) 0.3920(4) 0.0450(11) Uani 1 1 d . . . N3 N 0.4695(3) -0.0477(4) 0.5761(4) 0.0494(12) Uani 1 1 d . . . C1 C 0.3017(3) 0.0419(4) 0.4351(5) 0.0468(14) Uani 1 1 d . . . C2 C 0.2376(4) 0.0989(5) 0.3966(6) 0.0580(16) Uani 1 1 d . . . H2A H 0.2486 0.1558 0.4301 0.070 Uiso 1 1 calc R . . C3 C 0.1580(4) 0.0713(5) 0.3091(7) 0.0681(19) Uani 1 1 d . . . H3A H 0.1145 0.1090 0.2820 0.082 Uiso 1 1 calc R . . C4 C 0.1439(4) -0.0147(5) 0.2618(6) 0.0650(19) Uani 1 1 d . . . H4A H 0.0907 -0.0354 0.2019 0.078 Uiso 1 1 calc R . . C5 C 0.2094(3) -0.0679(4) 0.3047(5) 0.0527(15) Uani 1 1 d . . . H5A H 0.1991 -0.1249 0.2718 0.063 Uiso 1 1 calc R . . C6 C 0.4581(3) 0.0396(4) 0.5870(5) 0.0467(14) Uani 1 1 d . . . C7 C 0.5245(4) 0.0969(5) 0.6656(6) 0.0608(17) Uani 1 1 d . . . H7A H 0.5152 0.1568 0.6706 0.073 Uiso 1 1 calc R . . C8 C 0.6025(4) 0.0655(6) 0.7348(6) 0.067(2) Uani 1 1 d . . . H8A H 0.6468 0.1035 0.7872 0.081 Uiso 1 1 calc R . . C9 C 0.6153(4) -0.0248(6) 0.7263(6) 0.070(2) Uani 1 1 d . . . H9A H 0.6680 -0.0485 0.7736 0.083 Uiso 1 1 calc R . . C10 C 0.5485(4) -0.0768(5) 0.6470(6) 0.0642(18) Uani 1 1 d . . . H10A H 0.5573 -0.1366 0.6406 0.077 Uiso 1 1 calc R . . C11 C 0.3348(3) -0.2520(4) 0.3873(5) 0.0478(14) Uani 1 1 d . . . H11A H 0.3066 -0.2623 0.3015 0.057 Uiso 1 1 calc R . . C12 C 0.4199(3) -0.2535(4) 0.4714(5) 0.0480(14) Uani 1 1 d . . . H12A H 0.4502 -0.2645 0.4432 0.058 Uiso 1 1 calc R . . C13 C 0.4441(3) -0.3032(4) 0.5793(5) 0.0527(15) Uani 1 1 d . . . H13A H 0.4998 -0.2915 0.6554 0.063 Uiso 1 1 calc R . . C14 C 0.4237(4) -0.4033(5) 0.5390(6) 0.0647(18) Uani 1 1 d . . . H14A H 0.4439 -0.4424 0.6067 0.078 Uiso 1 1 calc R . . H14B H 0.4464 -0.4222 0.5021 0.078 Uiso 1 1 calc R . . C15 C 0.3275(4) -0.4019(4) 0.4441(6) 0.0606(17) Uani 1 1 d . . . H15A H 0.3071 -0.4197 0.3644 0.073 Uiso 1 1 calc R . . H15B H 0.3045 -0.4411 0.4686 0.073 Uiso 1 1 calc R . . C16 C 0.3070(3) -0.3026(4) 0.4448(5) 0.0504(15) Uani 1 1 d . . . H16A H 0.2508 -0.2906 0.4112 0.060 Uiso 1 1 calc R . . C17 C 0.3746(3) -0.2798(5) 0.5789(5) 0.0594(17) Uani 1 1 d . . . H17A H 0.3746 -0.2172 0.5967 0.071 Uiso 1 1 calc R . . H17B H 0.3736 -0.3178 0.6321 0.071 Uiso 1 1 calc R . . B1 B 0.3728(6) 0.3149(6) 0.4824(8) 0.070(2) Uani 1 1 d . . . F1 F 0.3836(3) 0.2611(3) 0.5718(4) 0.0975(14) Uani 1 1 d . . . F2 F 0.3757(3) 0.2589(3) 0.4082(4) 0.0985(14) Uani 1 1 d . . . F3 F 0.2973(3) 0.3525(4) 0.4147(5) 0.121(2) Uani 1 1 d . . . F4 F 0.4325(4) 0.3752(4) 0.5353(8) 0.152(3) 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 0.0454(5) 0.0465(5) 0.0527(5) 0.0030(3) 0.0302(4) 0.0024(3) N1 0.047(3) 0.043(3) 0.053(3) -0.003(2) 0.029(3) -0.004(2) N2 0.042(3) 0.043(3) 0.047(3) 0.000(2) 0.028(2) -0.003(2) N3 0.038(3) 0.058(3) 0.049(3) 0.009(2) 0.027(2) 0.003(2) C1 0.041(3) 0.060(4) 0.042(3) 0.011(3) 0.029(3) 0.004(3) C2 0.056(4) 0.051(4) 0.068(4) 0.004(3) 0.041(4) 0.006(3) C3 0.048(4) 0.069(5) 0.080(5) 0.015(4) 0.038(4) 0.015(4) C4 0.039(4) 0.077(5) 0.064(4) 0.014(4) 0.027(3) -0.002(3) C5 0.045(4) 0.057(4) 0.052(3) 0.003(3) 0.030(3) -0.003(3) C6 0.042(3) 0.059(4) 0.039(3) 0.005(3) 0.026(3) -0.005(3) C7 0.057(4) 0.074(5) 0.050(4) -0.008(3) 0.034(3) -0.018(3) C8 0.050(4) 0.097(6) 0.047(4) -0.010(4) 0.028(3) -0.026(4) C9 0.037(4) 0.106(7) 0.053(4) 0.010(4) 0.024(3) 0.000(4) C10 0.044(4) 0.081(5) 0.063(4) 0.018(4) 0.033(3) 0.012(3) C11 0.055(4) 0.044(3) 0.045(3) -0.002(3) 0.033(3) 0.004(3) C12 0.053(3) 0.042(3) 0.060(3) -0.001(3) 0.041(3) 0.001(3) C13 0.035(3) 0.054(4) 0.052(3) 0.001(3) 0.020(3) -0.003(3) C14 0.049(4) 0.056(4) 0.075(5) 0.004(4) 0.034(4) 0.003(3) C15 0.044(4) 0.056(4) 0.068(4) -0.006(3) 0.030(3) 0.000(3) C16 0.034(3) 0.055(4) 0.056(4) -0.001(3) 0.026(3) 0.003(3) C17 0.053(4) 0.067(5) 0.055(4) 0.003(3) 0.034(3) -0.003(3) B1 0.078(6) 0.050(5) 0.083(6) -0.005(4) 0.053(5) 0.003(4) F1 0.143(4) 0.055(3) 0.088(3) 0.000(2) 0.072(3) 0.004(3) F2 0.120(4) 0.085(3) 0.115(3) 0.006(3) 0.087(3) 0.025(3) F3 0.100(4) 0.169(6) 0.102(4) 0.033(4) 0.069(3) 0.070(4) F4 0.139(5) 0.099(5) 0.211(8) -0.030(4) 0.111(5) -0.049(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.957(5) . ? Cu1 N3 1.962(5) . ? Cu1 C12 2.030(6) . ? Cu1 C11 2.026(6) . ? N1 C1 1.382(7) . ? N1 C6 1.375(7) . ? N1 H1A 0.8600 . ? N2 C1 1.359(8) . ? N2 C5 1.352(7) . ? N3 C6 1.354(7) . ? N3 C10 1.361(7) . ? C1 C2 1.389(8) . ? C2 C3 1.369(9) . ? C2 H2A 0.9300 . ? C3 C4 1.394(10) . ? C3 H3A 0.9300 . ? C4 C5 1.361(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.395(8) . ? C7 C8 1.357(9) . ? C7 H7A 0.9300 . ? C8 C9 1.398(11) . ? C8 H8A 0.9300 . ? C9 C10 1.353(9) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.388(7) . ? C11 C16 1.506(8) . ? C11 H11A 0.9800 . ? C12 C13 1.488(8) . ? C12 H12A 0.9800 . ? C13 C17 1.527(8) . ? C13 C14 1.561(9) . ? C13 H13A 0.9800 . ? C14 C15 1.566(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.548(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.528(8) . ? C16 H16A 0.9800 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? B1 F4 1.327(10) . ? B1 F3 1.353(9) . ? B1 F2 1.396(10) . ? B1 F1 1.410(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 97.7(2) . . ? N2 Cu1 C12 151.3(2) . . ? N3 Cu1 C12 110.7(2) . . ? N2 Cu1 C11 111.3(2) . . ? N3 Cu1 C11 150.6(2) . . ? C12 Cu1 C11 40.0(2) . . ? C1 N1 C6 135.1(5) . . ? C1 N1 H1A 112.5 . . ? C6 N1 H1A 112.5 . . ? C1 N2 C5 116.4(5) . . ? C1 N2 Cu1 122.5(4) . . ? C5 N2 Cu1 121.0(4) . . ? C6 N3 C10 116.8(5) . . ? C6 N3 Cu1 122.5(4) . . ? C10 N3 Cu1 120.6(5) . . ? N2 C1 N1 120.8(5) . . ? N2 C1 C2 122.2(5) . . ? N1 C1 C2 117.0(6) . . ? C3 C2 C1 119.9(7) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 118.3(6) . . ? C2 C3 H3A 120.8 . . ? C4 C3 H3A 120.8 . . ? C5 C4 C3 118.9(6) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? N2 C5 C4 124.2(6) . . ? N2 C5 H5A 117.9 . . ? C4 C5 H5A 117.9 . . ? N3 C6 N1 121.0(5) . . ? N3 C6 C7 121.3(6) . . ? N1 C6 C7 117.7(6) . . ? C8 C7 C6 120.3(7) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? C7 C8 C9 119.1(6) . . ? C7 C8 H8A 120.5 . . ? C9 C8 H8A 120.5 . . ? C10 C9 C8 117.9(6) . . ? C10 C9 H9A 121.0 . . ? C8 C9 H9A 121.0 . . ? C9 C10 N3 124.6(7) . . ? C9 C10 H10A 117.7 . . ? N3 C10 H10A 117.7 . . ? C12 C11 C16 105.8(5) . . ? C12 C11 Cu1 70.2(3) . . ? C16 C11 Cu1 113.3(4) . . ? C12 C11 H11A 119.1 . . ? C16 C11 H11A 119.1 . . ? Cu1 C11 H11A 119.1 . . ? C11 C12 C13 107.1(5) . . ? C11 C12 Cu1 69.8(3) . . ? C13 C12 Cu1 113.1(4) . . ? C11 C12 H12A 118.9 . . ? C13 C12 H12A 118.9 . . ? Cu1 C12 H12A 118.9 . . ? C12 C13 C17 102.1(5) . . ? C12 C13 C14 105.2(5) . . ? C17 C13 C14 100.5(5) . . ? C12 C13 H13A 115.7 . . ? C17 C13 H13A 115.7 . . ? C14 C13 H13A 115.7 . . ? C13 C14 C15 101.8(5) . . ? C13 C14 H14A 111.4 . . ? C15 C14 H14A 111.4 . . ? C13 C14 H14B 111.4 . . ? C15 C14 H14B 111.4 . . ? H14A C14 H14B 109.3 . . ? C16 C15 C14 103.0(5) . . ? C16 C15 H15A 111.2 . . ? C14 C15 H15A 111.2 . . ? C16 C15 H15B 111.2 . . ? C14 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? C11 C16 C17 101.8(5) . . ? C11 C16 C15 105.1(5) . . ? C17 C16 C15 100.6(5) . . ? C11 C16 H16A 115.8 . . ? C17 C16 H16A 115.8 . . ? C15 C16 H16A 115.8 . . ? C13 C17 C16 94.0(5) . . ? C13 C17 H17A 112.9 . . ? C16 C17 H17A 112.9 . . ? C13 C17 H17B 112.9 . . ? C16 C17 H17B 112.9 . . ? H17A C17 H17B 110.3 . . ? F4 B1 F3 112.7(8) . . ? F4 B1 F2 110.1(8) . . ? F3 B1 F2 108.6(7) . . ? F4 B1 F1 109.5(7) . . ? F3 B1 F1 108.0(7) . . ? F2 B1 F1 107.7(7) . . ? 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 N2 C11 C12 -1.6(3) . . . . ? N3 Cu1 N2 C1 -2.6(4) . . . . ? C12 Cu1 N2 C1 169.9(4) . . . . ? C11 Cu1 N2 C1 172.4(4) . . . . ? N3 Cu1 N2 C5 -179.0(4) . . . . ? C12 Cu1 N2 C5 -6.4(7) . . . . ? C11 Cu1 N2 C5 -4.0(5) . . . . ? N2 Cu1 N3 C6 -2.9(4) . . . . ? C12 Cu1 N3 C6 -179.1(4) . . . . ? C11 Cu1 N3 C6 -173.4(4) . . . . ? N2 Cu1 N3 C10 -179.1(4) . . . . ? C12 Cu1 N3 C10 4.7(5) . . . . ? C11 Cu1 N3 C10 10.3(7) . . . . ? C5 N2 C1 N1 -177.8(5) . . . . ? Cu1 N2 C1 N1 5.7(7) . . . . ? C5 N2 C1 C2 3.2(8) . . . . ? Cu1 N2 C1 C2 -173.3(4) . . . . ? C6 N1 C1 N2 -3.7(9) . . . . ? C6 N1 C1 C2 175.4(6) . . . . ? N2 C1 C2 C3 -2.4(9) . . . . ? N1 C1 C2 C3 178.5(6) . . . . ? C1 C2 C3 C4 0.5(9) . . . . ? C2 C3 C4 C5 0.4(10) . . . . ? C1 N2 C5 C4 -2.2(8) . . . . ? Cu1 N2 C5 C4 174.4(5) . . . . ? C3 C4 C5 N2 0.4(9) . . . . ? C10 N3 C6 N1 -178.2(5) . . . . ? Cu1 N3 C6 N1 5.4(7) . . . . ? C10 N3 C6 C7 1.1(8) . . . . ? Cu1 N3 C6 C7 -175.3(4) . . . . ? C1 N1 C6 N3 -2.6(9) . . . . ? C1 N1 C6 C7 178.1(6) . . . . ? N3 C6 C7 C8 -1.0(9) . . . . ? N1 C6 C7 C8 178.3(5) . . . . ? C6 C7 C8 C9 -0.1(9) . . . . ? C7 C8 C9 C10 1.1(9) . . . . ? C8 C9 C10 N3 -1.1(10) . . . . ? C6 N3 C10 C9 0.0(8) . . . . ? Cu1 N3 C10 C9 176.4(5) . . . . ? N2 Cu1 C11 C12 -178.2(3) . . . . ? N3 Cu1 C11 C12 -8.2(6) . . . . ? N2 Cu1 C11 C16 -79.0(4) . . . . ? N3 Cu1 C11 C16 90.9(5) . . . . ? C12 Cu1 C11 C16 99.2(5) . . . . ? C16 C11 C12 C13 -0.6(6) . . . . ? Cu1 C11 C12 C13 108.9(4) . . . . ? C16 C11 C12 Cu1 -109.6(4) . . . . ? N2 Cu1 C12 C11 3.6(6) . . . . ? N3 Cu1 C12 C11 175.7(3) . . . . ? N2 Cu1 C12 C13 -97.0(5) . . . . ? N3 Cu1 C12 C13 75.1(4) . . . . ? C11 Cu1 C12 C13 -100.6(5) . . . . ? C11 C12 C13 C17 -32.2(6) . . . . ? Cu1 C12 C13 C17 42.6(5) . . . . ? C11 C12 C13 C14 72.3(6) . . . . ? Cu1 C12 C13 C14 147.2(4) . . . . ? C12 C13 C14 C15 -68.6(6) . . . . ? C17 C13 C14 C15 37.2(6) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? C12 C11 C16 C17 33.2(6) . . . . ? Cu1 C11 C16 C17 -41.6(5) . . . . ? C12 C11 C16 C15 -71.3(5) . . . . ? Cu1 C11 C16 C15 -146.1(4) . . . . ? C14 C15 C16 C11 69.3(6) . . . . ? C14 C15 C16 C17 -36.1(6) . . . . ? C12 C13 C17 C16 49.3(6) . . . . ? C14 C13 C17 C16 -58.9(5) . . . . ? C11 C16 C17 C13 -49.5(5) . . . . ? C15 C16 C17 C13 58.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F1 0.86 2.01 2.868(7) 176.9 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.523 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.143 _exptl_crystal_recrystallization_method 'sat. soln in MeOH cooled to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_sty2 _database_code_depnum_ccdc_archive 'CCDC 692447' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-phenylethene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-phenylethene)copper(i) tetrafluoroborate ; _chemical_melting_point 446 _chemical_formula_moiety 'C18 H17 Cu N3, B F4' _chemical_formula_sum 'C18 H17 B Cu F4 N3' _chemical_formula_weight 425.70 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' 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 12.503(3) _cell_length_b 10.368(2) _cell_length_c 13.827(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.70(3) _cell_angle_gamma 90.00 _cell_volume 1790.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1238 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 16.71 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6656 _exptl_absorpt_correction_T_max 0.8230 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 21029 _diffrn_reflns_av_R_equivalents 0.1717 _diffrn_reflns_av_sigmaI/netI 0.2114 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4329 _reflns_number_gt 1505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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^)+(0.0920P)^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 4329 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2088 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 0.835 _refine_ls_restrained_S_all 0.835 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.31788(6) -0.04092(7) 0.15996(5) 0.0520(3) Uani 1 1 d . . . N1 N 0.4609(4) 0.1890(5) 0.0923(4) 0.0607(14) Uani 1 1 d . . . H1 H 0.4917 0.2593 0.0758 0.073 Uiso 1 1 calc R . . N2 N 0.3424(4) 0.0275(5) 0.0308(3) 0.0496(12) Uani 1 1 d . . . N3 N 0.4249(4) 0.0666(4) 0.2308(3) 0.0492(12) Uani 1 1 d . . . C1 C 0.4012(5) 0.1304(6) 0.0159(4) 0.0532(16) Uani 1 1 d . . . C2 C 0.4098(5) 0.1870(7) -0.0759(5) 0.0695(19) Uani 1 1 d . . . H2 H 0.4512 0.2606 -0.0832 0.083 Uiso 1 1 calc R . . C3 C 0.3568(6) 0.1324(8) -0.1543(5) 0.074(2) Uani 1 1 d . . . H3 H 0.3618 0.1684 -0.2155 0.089 Uiso 1 1 calc R . . C4 C 0.2954(5) 0.0230(7) -0.1416(5) 0.0671(18) Uani 1 1 d . . . H4 H 0.2586 -0.0164 -0.1936 0.080 Uiso 1 1 calc R . . C5 C 0.2908(5) -0.0250(6) -0.0498(5) 0.0623(17) Uani 1 1 d . . . H5 H 0.2498 -0.0986 -0.0414 0.075 Uiso 1 1 calc R . . C6 C 0.4805(5) 0.1579(5) 0.1871(4) 0.0501(15) Uani 1 1 d . . . C7 C 0.5649(5) 0.2260(6) 0.2385(5) 0.0591(17) Uani 1 1 d . . . H7 H 0.6035 0.2895 0.2079 0.071 Uiso 1 1 calc R . . C8 C 0.5876(5) 0.1962(6) 0.3329(5) 0.0676(18) Uani 1 1 d . . . H8 H 0.6431 0.2385 0.3670 0.081 Uiso 1 1 calc R . . C9 C 0.5305(6) 0.1063(6) 0.3775(5) 0.076(2) Uani 1 1 d . . . H9 H 0.5451 0.0872 0.4424 0.091 Uiso 1 1 calc R . . C10 C 0.4499(6) 0.0426(6) 0.3257(4) 0.0648(18) Uani 1 1 d . . . H10 H 0.4108 -0.0197 0.3571 0.078 Uiso 1 1 calc R . . C11 C 0.2041(5) -0.1753(6) 0.1526(5) 0.0624(17) Uani 1 1 d . . . H11B H 0.1310 -0.1447 0.1437 0.075 Uiso 1 1 calc R . . H11A H 0.2187 -0.2513 0.1145 0.075 Uiso 1 1 calc R . . C12 C 0.2481(5) -0.1733(5) 0.2466(4) 0.0569(17) Uani 1 1 d . . . H12 H 0.2020 -0.1374 0.2952 0.068 Uiso 1 1 calc R . . C13 C 0.3321(5) -0.2646(5) 0.2844(4) 0.0499(15) Uani 1 1 d . . . C14 C 0.3577(5) -0.2677(6) 0.3833(5) 0.0629(18) Uani 1 1 d . . . H14 H 0.3195 -0.2180 0.4257 0.075 Uiso 1 1 calc R . . C15 C 0.4417(6) -0.3467(7) 0.4184(5) 0.074(2) Uani 1 1 d . . . H15 H 0.4595 -0.3497 0.4844 0.088 Uiso 1 1 calc R . . C16 C 0.4975(6) -0.4192(7) 0.3558(7) 0.079(2) Uani 1 1 d . . . H16 H 0.5531 -0.4713 0.3799 0.095 Uiso 1 1 calc R . . C17 C 0.4736(6) -0.4170(6) 0.2586(6) 0.075(2) Uani 1 1 d . . . H17 H 0.5137 -0.4653 0.2166 0.089 Uiso 1 1 calc R . . C18 C 0.3886(5) -0.3416(6) 0.2228(5) 0.0606(17) Uani 1 1 d . . . H18 H 0.3696 -0.3430 0.1570 0.073 Uiso 1 1 calc R . . B1 B 0.7001(8) 0.4459(10) 0.0489(7) 0.081(3) Uani 1 1 d . . . F1 F 0.6194(5) 0.3646(5) 0.0241(3) 0.148(2) Uani 1 1 d . . . F2 F 0.7288(6) 0.5166(6) -0.0189(3) 0.185(3) Uani 1 1 d . . . F3 F 0.7834(7) 0.3569(7) 0.0666(7) 0.222(4) Uani 1 1 d . . . F4 F 0.6909(4) 0.5015(5) 0.1334(3) 0.1183(17) 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 0.0415(5) 0.0543(5) 0.0597(5) 0.0039(4) -0.0025(3) -0.0019(4) N1 0.061(4) 0.063(3) 0.058(4) 0.010(3) 0.005(3) -0.015(3) N2 0.040(3) 0.052(3) 0.056(3) -0.001(3) -0.001(2) 0.000(2) N3 0.055(3) 0.049(3) 0.043(3) 0.005(2) -0.005(2) -0.004(2) C1 0.042(4) 0.063(4) 0.055(4) 0.002(3) 0.004(3) 0.014(3) C2 0.059(5) 0.083(5) 0.068(5) 0.016(4) 0.004(4) -0.003(4) C3 0.068(5) 0.103(6) 0.050(5) 0.013(4) 0.003(4) 0.016(4) C4 0.051(4) 0.095(5) 0.055(4) -0.008(4) -0.003(3) 0.018(4) C5 0.061(5) 0.062(4) 0.062(5) 0.000(4) -0.013(4) 0.001(3) C6 0.048(4) 0.050(4) 0.053(4) 0.005(3) 0.005(3) 0.005(3) C7 0.046(4) 0.067(4) 0.065(5) -0.011(4) 0.008(3) -0.016(3) C8 0.063(5) 0.074(5) 0.065(5) -0.006(4) -0.010(4) -0.011(4) C9 0.103(6) 0.066(4) 0.058(4) 0.007(4) -0.018(4) -0.022(4) C10 0.083(5) 0.058(4) 0.054(4) 0.004(4) 0.000(4) -0.013(4) C11 0.041(4) 0.064(4) 0.081(5) 0.003(4) -0.009(4) -0.011(3) C12 0.040(4) 0.067(4) 0.064(4) 0.005(3) 0.008(3) -0.004(3) C13 0.041(4) 0.050(4) 0.060(4) 0.005(3) 0.011(3) -0.006(3) C14 0.065(5) 0.061(4) 0.062(5) 0.003(3) 0.004(4) -0.006(3) C15 0.072(5) 0.074(5) 0.072(5) 0.017(4) -0.026(4) -0.008(4) C16 0.060(5) 0.071(5) 0.106(7) 0.014(5) -0.009(5) -0.001(4) C17 0.062(5) 0.079(5) 0.084(6) 0.004(4) 0.021(4) 0.011(4) C18 0.056(4) 0.069(4) 0.057(4) 0.005(3) 0.003(4) -0.009(3) B1 0.083(7) 0.086(7) 0.075(7) -0.011(6) 0.013(5) -0.030(6) F1 0.158(5) 0.205(6) 0.079(3) 0.023(3) -0.016(3) -0.118(5) F2 0.272(8) 0.203(6) 0.080(3) 0.015(4) 0.024(4) -0.165(6) F3 0.163(7) 0.158(6) 0.343(12) -0.072(7) -0.011(7) 0.014(5) F4 0.117(4) 0.157(4) 0.081(3) -0.035(3) 0.010(3) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.959(5) . ? Cu1 N3 1.967(5) . ? Cu1 C11 1.990(6) . ? Cu1 C12 2.044(5) . ? N1 C6 1.360(7) . ? N1 C1 1.403(7) . ? N1 H1 0.8600 . ? N2 C1 1.318(7) . ? N2 C5 1.374(7) . ? N3 C6 1.335(7) . ? N3 C10 1.357(7) . ? C1 C2 1.408(8) . ? C2 C3 1.366(9) . ? C2 H2 0.9300 . ? C3 C4 1.386(9) . ? C3 H3 0.9300 . ? C4 C5 1.366(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.431(7) . ? C7 C8 1.358(8) . ? C7 H7 0.9300 . ? C8 C9 1.341(8) . ? C8 H8 0.9300 . ? C9 C10 1.377(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.387(8) . ? C11 H11B 0.9700 . ? C11 H11A 0.9700 . ? C12 C13 1.489(8) . ? C12 H12 0.9800 . ? C13 C18 1.385(8) . ? C13 C14 1.391(8) . ? C14 C15 1.401(9) . ? C14 H14 0.9300 . ? C15 C16 1.363(9) . ? C15 H15 0.9300 . ? C16 C17 1.364(10) . ? C16 H16 0.9300 . ? C17 C18 1.391(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? B1 F2 1.256(10) . ? B1 F4 1.314(9) . ? B1 F1 1.346(9) . ? B1 F3 1.404(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 96.7(2) . . ? N2 Cu1 C11 110.4(2) . . ? N3 Cu1 C11 152.9(2) . . ? N2 Cu1 C12 150.1(2) . . ? N3 Cu1 C12 112.8(2) . . ? C11 Cu1 C12 40.2(2) . . ? C6 N1 C1 133.5(5) . . ? C6 N1 H1 113.3 . . ? C1 N1 H1 113.3 . . ? C1 N2 C5 116.0(5) . . ? C1 N2 Cu1 123.2(4) . . ? C5 N2 Cu1 120.6(4) . . ? C6 N3 C10 117.9(5) . . ? C6 N3 Cu1 122.1(4) . . ? C10 N3 Cu1 119.8(4) . . ? N2 C1 N1 120.9(5) . . ? N2 C1 C2 123.0(6) . . ? N1 C1 C2 116.0(6) . . ? C3 C2 C1 119.2(6) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.3(6) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 117.6(6) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? C4 C5 N2 124.8(6) . . ? C4 C5 H5 117.6 . . ? N2 C5 H5 117.6 . . ? N3 C6 N1 122.1(5) . . ? N3 C6 C7 120.7(5) . . ? N1 C6 C7 117.2(5) . . ? C8 C7 C6 118.8(6) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C9 C8 C7 120.5(6) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.1(6) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N3 C10 C9 123.0(6) . . ? N3 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? C12 C11 Cu1 72.0(3) . . ? C12 C11 H11B 116.4 . . ? Cu1 C11 H11B 116.4 . . ? C12 C11 H11A 116.4 . . ? Cu1 C11 H11A 116.4 . . ? H11B C11 H11A 113.4 . . ? C11 C12 C13 124.1(6) . . ? C11 C12 Cu1 67.8(3) . . ? C13 C12 Cu1 108.6(4) . . ? C11 C12 H12 115.4 . . ? C13 C12 H12 115.4 . . ? Cu1 C12 H12 115.4 . . ? C18 C13 C14 119.3(6) . . ? C18 C13 C12 121.5(6) . . ? C14 C13 C12 119.1(6) . . ? C13 C14 C15 119.3(6) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.0(7) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 121.5(7) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 119.2(7) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C13 C18 C17 120.7(6) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? F2 B1 F4 116.6(8) . . ? F2 B1 F1 114.4(8) . . ? F4 B1 F1 113.9(8) . . ? F2 B1 F3 106.2(9) . . ? F4 B1 F3 103.2(8) . . ? F1 B1 F3 100.0(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 C11 C12 N3 N2 -6.8(4) . . . . ? N3 Cu1 N2 C1 -10.6(5) . . . . ? C11 Cu1 N2 C1 169.4(4) . . . . ? C12 Cu1 N2 C1 178.6(4) . . . . ? N3 Cu1 N2 C5 174.8(4) . . . . ? C11 Cu1 N2 C5 -5.2(5) . . . . ? C12 Cu1 N2 C5 4.0(7) . . . . ? N2 Cu1 N3 C6 4.2(4) . . . . ? C11 Cu1 N3 C6 -175.7(5) . . . . ? C12 Cu1 N3 C6 179.2(4) . . . . ? N2 Cu1 N3 C10 -170.9(5) . . . . ? C11 Cu1 N3 C10 9.2(8) . . . . ? C12 Cu1 N3 C10 4.1(5) . . . . ? C5 N2 C1 N1 -177.4(5) . . . . ? Cu1 N2 C1 N1 7.8(7) . . . . ? C5 N2 C1 C2 1.5(8) . . . . ? Cu1 N2 C1 C2 -173.3(4) . . . . ? C6 N1 C1 N2 5.3(10) . . . . ? C6 N1 C1 C2 -173.7(6) . . . . ? N2 C1 C2 C3 -1.2(10) . . . . ? N1 C1 C2 C3 177.8(6) . . . . ? C1 C2 C3 C4 0.2(10) . . . . ? C2 C3 C4 C5 0.3(10) . . . . ? C3 C4 C5 N2 0.1(10) . . . . ? C1 N2 C5 C4 -1.0(9) . . . . ? Cu1 N2 C5 C4 174.0(5) . . . . ? C10 N3 C6 N1 -179.8(5) . . . . ? Cu1 N3 C6 N1 5.0(7) . . . . ? C10 N3 C6 C7 1.2(8) . . . . ? Cu1 N3 C6 C7 -174.0(4) . . . . ? C1 N1 C6 N3 -12.6(10) . . . . ? C1 N1 C6 C7 166.5(6) . . . . ? N3 C6 C7 C8 -0.1(9) . . . . ? N1 C6 C7 C8 -179.1(6) . . . . ? C6 C7 C8 C9 -1.2(10) . . . . ? C7 C8 C9 C10 1.3(11) . . . . ? C6 N3 C10 C9 -1.2(9) . . . . ? Cu1 N3 C10 C9 174.1(5) . . . . ? C8 C9 C10 N3 -0.1(11) . . . . ? N2 Cu1 C11 C12 172.8(3) . . . . ? N3 Cu1 C11 C12 -7.3(7) . . . . ? Cu1 C11 C12 C13 -98.0(5) . . . . ? N2 Cu1 C12 C11 -13.5(6) . . . . ? N3 Cu1 C12 C11 176.4(4) . . . . ? N2 Cu1 C12 C13 106.6(5) . . . . ? N3 Cu1 C12 C13 -63.5(5) . . . . ? C11 Cu1 C12 C13 120.2(6) . . . . ? C11 C12 C13 C18 13.7(9) . . . . ? Cu1 C12 C13 C18 -61.6(6) . . . . ? C11 C12 C13 C14 -169.5(5) . . . . ? Cu1 C12 C13 C14 115.1(5) . . . . ? C18 C13 C14 C15 1.4(9) . . . . ? C12 C13 C14 C15 -175.5(5) . . . . ? C13 C14 C15 C16 0.1(9) . . . . ? C14 C15 C16 C17 0.0(11) . . . . ? C15 C16 C17 C18 -1.7(11) . . . . ? C14 C13 C18 C17 -3.0(9) . . . . ? C12 C13 C18 C17 173.8(5) . . . . ? C16 C17 C18 C13 3.2(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 F1 0.86 2.09 2.882(6) 153.2 . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.696 _refine_diff_density_min -0.843 _refine_diff_density_rms 0.106 _exptl_crystal_recrystallization_method 'sat. soln in MeOH cooled to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_dpac3o _database_code_depnum_ccdc_archive 'CCDC 693280' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h2-cis-3-octene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta2-cis-3-octene)copper(i) tetrafluoroborate ; _chemical_melting_point 415 _chemical_formula_moiety 'C18 H25 Cu N3, B F4' _chemical_formula_sum 'C18 H25 B Cu F4 N3' _chemical_formula_weight 433.76 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' 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' 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' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6515(19) _cell_length_b 10.106(2) _cell_length_c 11.396(2) _cell_angle_alpha 69.02(3) _cell_angle_beta 77.70(3) _cell_angle_gamma 80.75(3) _cell_volume 1009.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1760 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 18.15 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 1.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6497 _exptl_absorpt_correction_T_max 0.7438 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 12398 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4798 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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. Disordered atoms F(1)-F(4) and F(1A)-F(4A) were refined with 50:50 site occupancies. For initial refinement cycles, similar distance restraints (SADI) were placed on all B-F and F-F distances, in addition to similar ADP restraints (SIMU) and rigid bond restraints (DELU) for all F atoms. Restraints were lifted for final refinement cycles. ; _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^)+(0.0845P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4798 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1463 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1689 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 1.46475(6) 0.40030(5) 1.25838(4) 0.0931(3) Uani 1 1 d . . . N1 N 1.5857(4) 0.6229(4) 1.3379(3) 0.0955(10) Uani 1 1 d . . . H1A H 1.6222 0.6883 1.3498 0.115 Uiso 1 1 calc R . . N2 N 1.6439(4) 0.3940(4) 1.3190(3) 0.0894(10) Uani 1 1 d . . . N3 N 1.3783(4) 0.5811(3) 1.2833(3) 0.0855(9) Uani 1 1 d . . . C1 C 1.6798(5) 0.5042(5) 1.3429(4) 0.0871(12) Uani 1 1 d . . . C2 C 1.8111(6) 0.5001(5) 1.3744(4) 0.1010(13) Uani 1 1 d . . . H2A H 1.8349 0.5777 1.3891 0.121 Uiso 1 1 calc R . . C3 C 1.9062(6) 0.3828(6) 1.3841(4) 0.1111(14) Uani 1 1 d . . . H3A H 1.9951 0.3800 1.4046 0.133 Uiso 1 1 calc R . . C4 C 1.8687(6) 0.2688(6) 1.3630(5) 0.1144(15) Uani 1 1 d . . . H4A H 1.9307 0.1867 1.3704 0.137 Uiso 1 1 calc R . . C5 C 1.7405(7) 0.2789(5) 1.3317(4) 0.1041(14) Uani 1 1 d . . . H5A H 1.7160 0.2012 1.3176 0.125 Uiso 1 1 calc R . . C6 C 1.4472(5) 0.6618(4) 1.3184(4) 0.0839(11) Uani 1 1 d . . . C7 C 1.3828(6) 0.7885(4) 1.3370(4) 0.0959(13) Uani 1 1 d . . . H7A H 1.4333 0.8422 1.3617 0.115 Uiso 1 1 calc R . . C8 C 1.2462(7) 0.8326(5) 1.3187(4) 0.1089(14) Uani 1 1 d . . . H8A H 1.2021 0.9170 1.3303 0.131 Uiso 1 1 calc R . . C9 C 1.1740(6) 0.7503(6) 1.2827(4) 0.1131(15) Uani 1 1 d . . . H9A H 1.0803 0.7777 1.2696 0.136 Uiso 1 1 calc R . . C10 C 1.2422(6) 0.6298(5) 1.2669(4) 0.0992(13) Uani 1 1 d . . . H10A H 1.1920 0.5753 1.2428 0.119 Uiso 1 1 calc R . . C11 C 1.4714(6) 0.2322(5) 1.1994(4) 0.0975(14) Uani 1 1 d . . . H11A H 1.4630 0.1417 1.2701 0.117 Uiso 1 1 calc R . . C12 C 1.3439(7) 0.3116(5) 1.1848(5) 0.1040(14) Uani 1 1 d . . . H12A H 1.2648 0.2655 1.2481 0.125 Uiso 1 1 calc R . . C13 C 1.5902(5) 0.2242(5) 1.0923(4) 0.1135(15) Uani 1 1 d . . . H13A H 1.5749 0.3040 1.0161 0.136 Uiso 1 1 calc R . . H13B H 1.6795 0.2324 1.1141 0.136 Uiso 1 1 calc R . . C14 C 1.2978(7) 0.4062(6) 1.0577(5) 0.1241(17) Uani 1 1 d . . . H14A H 1.2579 0.4980 1.0647 0.149 Uiso 1 1 calc R . . H14B H 1.3816 0.4219 0.9918 0.149 Uiso 1 1 calc R . . C15 C 1.6015(6) 0.0893(6) 1.0641(5) 0.1350(18) Uani 1 1 d . . . H15A H 1.6785 0.0899 0.9951 0.202 Uiso 1 1 calc R . . H15B H 1.5141 0.0813 1.0408 0.202 Uiso 1 1 calc R . . H15C H 1.6191 0.0098 1.1385 0.202 Uiso 1 1 calc R . . C16 C 1.1905(10) 0.3470(10) 1.0163(7) 0.210(4) Uani 1 1 d . . . H16A H 1.1027 0.4036 1.0343 0.253 Uiso 1 1 calc R . . H16B H 1.2163 0.3809 0.9242 0.253 Uiso 1 1 calc R . . C17 C 1.1538(13) 0.2413(9) 1.0367(11) 0.277(7) Uani 1 1 d . . . H17A H 1.1335 0.2030 1.1291 0.332 Uiso 1 1 calc R . . H17B H 1.2391 0.1855 1.0120 0.332 Uiso 1 1 calc R . . C18 C 1.0381(8) 0.1939(9) 0.9956(9) 0.202(3) Uani 1 1 d . . . H18A H 0.9774 0.1387 1.0694 0.303 Uiso 1 1 calc R . . H18B H 1.0798 0.1370 0.9430 0.303 Uiso 1 1 calc R . . H18C H 0.9830 0.2758 0.9480 0.303 Uiso 1 1 calc R . . B1 B 1.7553(7) 0.8681(7) 1.4452(7) 0.0974(16) Uani 1 1 d . . . F1 F 1.6464(13) 0.844(3) 1.424(3) 0.304(11) Uani 0.50 1 d P A 1 F2 F 1.8275(17) 0.7514(15) 1.4979(14) 0.211(6) Uani 0.50 1 d P A 1 F3 F 1.8557(17) 0.9177(15) 1.3468(15) 0.214(5) Uani 0.50 1 d P A 1 F4 F 1.7335(14) 0.9478(9) 1.5245(6) 0.128(3) Uani 0.50 1 d P A 1 F1A F 1.8599(17) 0.8951(12) 1.476(2) 0.234(7) Uani 0.50 1 d P A 2 F2A F 1.7127(18) 0.7336(9) 1.5106(6) 0.142(4) Uani 0.50 1 d P A 2 F3A F 1.756(2) 0.8826(14) 1.3274(9) 0.232(7) Uani 0.50 1 d P A 2 F4A F 1.6435(11) 0.9548(10) 1.449(2) 0.226(6) Uani 0.50 1 d P A 2 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 0.1244(5) 0.0908(4) 0.0813(4) -0.0437(3) -0.0107(3) -0.0319(3) N1 0.117(3) 0.078(2) 0.111(3) -0.048(2) -0.019(2) -0.025(2) N2 0.114(3) 0.086(2) 0.079(2) -0.0371(18) -0.0150(19) -0.020(2) N3 0.104(3) 0.088(2) 0.076(2) -0.0376(17) -0.0084(18) -0.025(2) C1 0.108(3) 0.088(3) 0.073(3) -0.033(2) -0.003(2) -0.035(3) C2 0.116(4) 0.101(4) 0.100(3) -0.040(3) -0.016(3) -0.034(3) C3 0.108(4) 0.124(4) 0.100(3) -0.035(3) -0.012(3) -0.019(3) C4 0.126(4) 0.114(4) 0.107(4) -0.046(3) -0.021(3) 0.004(3) C5 0.137(4) 0.093(3) 0.092(3) -0.041(3) -0.020(3) -0.014(3) C6 0.108(3) 0.083(3) 0.065(2) -0.027(2) -0.006(2) -0.026(2) C7 0.140(4) 0.077(3) 0.081(3) -0.036(2) -0.015(3) -0.021(3) C8 0.145(5) 0.092(3) 0.093(3) -0.039(3) -0.018(3) -0.002(3) C9 0.125(4) 0.124(4) 0.089(3) -0.038(3) -0.021(3) 0.003(3) C10 0.111(4) 0.113(4) 0.087(3) -0.049(3) -0.010(3) -0.020(3) C11 0.139(4) 0.087(3) 0.081(3) -0.041(2) 0.001(3) -0.046(3) C12 0.137(4) 0.095(3) 0.100(4) -0.047(3) -0.006(3) -0.050(3) C13 0.145(4) 0.114(4) 0.097(3) -0.053(3) 0.003(3) -0.045(3) C14 0.182(5) 0.115(4) 0.100(4) -0.047(3) -0.037(3) -0.042(3) C15 0.173(5) 0.122(4) 0.121(4) -0.066(3) 0.009(4) -0.029(4) C16 0.296(10) 0.197(8) 0.147(6) 0.006(6) -0.091(6) -0.124(8) C17 0.408(16) 0.144(7) 0.326(14) -0.019(8) -0.197(13) -0.119(9) C18 0.156(5) 0.226(8) 0.293(11) -0.134(8) -0.081(6) -0.042(5) B1 0.085(4) 0.098(5) 0.113(5) -0.032(4) -0.039(4) 0.004(4) F1 0.140(9) 0.37(2) 0.60(3) -0.37(2) -0.153(15) 0.044(12) F2 0.237(12) 0.143(10) 0.277(14) -0.097(9) -0.108(12) 0.068(10) F3 0.153(9) 0.307(15) 0.195(11) -0.134(11) 0.062(9) -0.058(9) F4 0.184(8) 0.110(5) 0.117(4) -0.072(4) 0.012(5) -0.064(5) F1A 0.178(10) 0.167(10) 0.42(2) -0.115(11) -0.173(14) 0.010(7) F2A 0.254(13) 0.087(5) 0.097(4) -0.039(3) 0.006(6) -0.079(8) F3A 0.237(14) 0.332(16) 0.096(6) 0.023(7) -0.059(7) -0.120(13) F4A 0.118(7) 0.115(6) 0.40(2) -0.056(9) -0.016(10) 0.014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.974(3) . ? Cu1 N2 1.978(4) . ? Cu1 C11 2.026(4) . ? Cu1 C12 2.038(4) . ? N1 C6 1.373(5) . ? N1 C1 1.374(5) . ? N1 H1A 0.8600 . ? N2 C1 1.348(5) . ? N2 C5 1.353(6) . ? N3 C6 1.337(5) . ? N3 C10 1.353(6) . ? C1 C2 1.379(6) . ? C2 C3 1.363(6) . ? C2 H2A 0.9300 . ? C3 C4 1.373(7) . ? C3 H3A 0.9300 . ? C4 C5 1.338(7) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.398(6) . ? C7 C8 1.357(7) . ? C7 H7A 0.9300 . ? C8 C9 1.378(7) . ? C8 H8A 0.9300 . ? C9 C10 1.340(6) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.363(6) . ? C11 C13 1.503(6) . ? C11 H11A 0.9800 . ? C12 C14 1.536(7) . ? C12 H12A 0.9800 . ? C13 C15 1.491(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C16 1.504(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.109(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.500(10) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? B1 F1 1.207(11) . ? B1 F1A 1.234(10) . ? B1 F4A 1.280(10) . ? B1 F2 1.282(11) . ? B1 F3A 1.296(12) . ? B1 F3 1.319(12) . ? B1 F4 1.377(9) . ? B1 F2A 1.377(10) . ? 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 N3 Cu1 N2 96.15(16) . . ? N3 Cu1 C11 153.9(2) . . ? N2 Cu1 C11 109.9(2) . . ? N3 Cu1 C12 114.8(2) . . ? N2 Cu1 C12 149.1(2) . . ? C11 Cu1 C12 39.19(17) . . ? C6 N1 C1 135.2(3) . . ? C6 N1 H1A 112.4 . . ? C1 N1 H1A 112.4 . . ? C1 N2 C5 116.8(4) . . ? C1 N2 Cu1 122.8(3) . . ? C5 N2 Cu1 120.3(3) . . ? C6 N3 C10 115.8(4) . . ? C6 N3 Cu1 123.3(3) . . ? C10 N3 Cu1 120.9(3) . . ? N2 C1 N1 120.7(4) . . ? N2 C1 C2 120.9(5) . . ? N1 C1 C2 118.4(4) . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 119.0(5) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C5 C4 C3 118.2(5) . . ? C5 C4 H4A 120.9 . . ? C3 C4 H4A 120.9 . . ? C4 C5 N2 124.8(5) . . ? C4 C5 H5A 117.6 . . ? N2 C5 H5A 117.6 . . ? N3 C6 N1 120.9(4) . . ? N3 C6 C7 122.1(4) . . ? N1 C6 C7 116.9(4) . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? C7 C8 C9 118.8(5) . . ? C7 C8 H8A 120.6 . . ? C9 C8 H8A 120.6 . . ? C10 C9 C8 118.4(5) . . ? C10 C9 H9A 120.8 . . ? C8 C9 H9A 120.8 . . ? C9 C10 N3 125.3(5) . . ? C9 C10 H10A 117.4 . . ? N3 C10 H10A 117.4 . . ? C12 C11 C13 125.0(5) . . ? C12 C11 Cu1 70.9(3) . . ? C13 C11 Cu1 115.3(3) . . ? C12 C11 H11A 112.9 . . ? C13 C11 H11A 112.9 . . ? Cu1 C11 H11A 112.9 . . ? C11 C12 C14 126.0(5) . . ? C11 C12 Cu1 69.9(3) . . ? C14 C12 Cu1 116.2(3) . . ? C11 C12 H12A 112.6 . . ? C14 C12 H12A 112.6 . . ? Cu1 C12 H12A 112.6 . . ? C15 C13 C11 113.0(4) . . ? C15 C13 H13A 109.0 . . ? C11 C13 H13A 109.0 . . ? C15 C13 H13B 109.0 . . ? C11 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C16 C14 C12 114.8(5) . . ? C16 C14 H14A 108.6 . . ? C12 C14 H14A 108.6 . . ? C16 C14 H14B 108.6 . . ? C12 C14 H14B 108.6 . . ? H14A C14 H14B 107.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C14 137.2(9) . . ? C17 C16 H16A 102.8 . . ? C14 C16 H16A 102.8 . . ? C17 C16 H16B 102.8 . . ? C14 C16 H16B 102.8 . . ? H16A C16 H16B 105.0 . . ? C16 C17 C18 133.1(10) . . ? C16 C17 H17A 104.0 . . ? C18 C17 H17A 104.0 . . ? C16 C17 H17B 104.0 . . ? C18 C17 H17B 104.0 . . ? H17A C17 H17B 105.4 . . ? 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 . . ? F1 B1 F1A 174.4(17) . . ? F1 B1 F4A 60.2(9) . . ? F1A B1 F4A 116.1(11) . . ? F1 B1 F2 110.2(13) . . ? F1A B1 F2 70.7(9) . . ? F4A B1 F2 149.7(12) . . ? F1 B1 F3A 65.3(12) . . ? F1A B1 F3A 119.9(13) . . ? F4A B1 F3A 92.8(12) . . ? F2 B1 F3A 109.6(11) . . ? F1 B1 F3 117.8(16) . . ? F1A B1 F3 67.2(10) . . ? F4A B1 F3 114.0(10) . . ? F2 B1 F3 96.1(11) . . ? F3A B1 F3 52.8(8) . . ? F1 B1 F4 113.5(11) . . ? F1A B1 F4 61.4(9) . . ? F4A B1 F4 59.5(9) . . ? F2 B1 F4 107.3(9) . . ? F3A B1 F4 140.6(9) . . ? F3 B1 F4 110.3(8) . . ? F1 B1 F2A 63.4(12) . . ? F1A B1 F2A 115.5(11) . . ? F4A B1 F2A 106.4(9) . . ? F2 B1 F2A 49.8(7) . . ? F3A B1 F2A 103.1(8) . . ? F3 B1 F2A 132.6(9) . . ? F4 B1 F2A 111.0(6) . . ? 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 N2 C11 C12 -2.1(3) . . . . ? N3 Cu1 N2 C1 -9.3(3) . . . . ? C11 Cu1 N2 C1 168.2(3) . . . . ? C12 Cu1 N2 C1 168.7(3) . . . . ? N3 Cu1 N2 C5 174.3(3) . . . . ? C11 Cu1 N2 C5 -8.2(4) . . . . ? C12 Cu1 N2 C5 -7.7(5) . . . . ? N2 Cu1 N3 C6 5.8(3) . . . . ? C11 Cu1 N3 C6 -168.9(3) . . . . ? C12 Cu1 N3 C6 -173.1(3) . . . . ? N2 Cu1 N3 C10 -173.3(3) . . . . ? C11 Cu1 N3 C10 12.0(5) . . . . ? C12 Cu1 N3 C10 7.8(4) . . . . ? C5 N2 C1 N1 -177.1(4) . . . . ? Cu1 N2 C1 N1 6.4(5) . . . . ? C5 N2 C1 C2 2.2(6) . . . . ? Cu1 N2 C1 C2 -174.3(3) . . . . ? C6 N1 C1 N2 3.9(7) . . . . ? C6 N1 C1 C2 -175.4(4) . . . . ? N2 C1 C2 C3 -1.2(7) . . . . ? N1 C1 C2 C3 178.1(4) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C2 C3 C4 C5 1.1(7) . . . . ? C3 C4 C5 N2 0.0(8) . . . . ? C1 N2 C5 C4 -1.6(7) . . . . ? Cu1 N2 C5 C4 175.0(4) . . . . ? C10 N3 C6 N1 179.9(3) . . . . ? Cu1 N3 C6 N1 0.8(5) . . . . ? C10 N3 C6 C7 0.0(5) . . . . ? Cu1 N3 C6 C7 -179.1(3) . . . . ? C1 N1 C6 N3 -8.0(7) . . . . ? C1 N1 C6 C7 171.9(4) . . . . ? N3 C6 C7 C8 -0.3(6) . . . . ? N1 C6 C7 C8 179.8(4) . . . . ? C6 C7 C8 C9 0.4(7) . . . . ? C7 C8 C9 C10 -0.1(7) . . . . ? C8 C9 C10 N3 -0.2(7) . . . . ? C6 N3 C10 C9 0.2(6) . . . . ? Cu1 N3 C10 C9 179.4(3) . . . . ? N3 Cu1 C11 C12 -6.1(5) . . . . ? N2 Cu1 C11 C12 179.6(3) . . . . ? N3 Cu1 C11 C13 114.5(5) . . . . ? N2 Cu1 C11 C13 -59.9(4) . . . . ? C12 Cu1 C11 C13 120.5(5) . . . . ? C13 C11 C12 C14 0.3(7) . . . . ? Cu1 C11 C12 C14 108.3(4) . . . . ? C13 C11 C12 Cu1 -108.0(4) . . . . ? N3 Cu1 C12 C11 177.1(2) . . . . ? N2 Cu1 C12 C11 -0.8(5) . . . . ? N3 Cu1 C12 C14 55.8(5) . . . . ? N2 Cu1 C12 C14 -122.0(4) . . . . ? C11 Cu1 C12 C14 -121.2(6) . . . . ? C12 C11 C13 C15 -103.8(6) . . . . ? Cu1 C11 C13 C15 172.5(4) . . . . ? C11 C12 C14 C16 105.9(7) . . . . ? Cu1 C12 C14 C16 -170.8(6) . . . . ? C12 C14 C16 C17 -21(2) . . . . ? C14 C16 C17 C18 175.7(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F1 0.86 2.10 2.921(13) 160.2 . _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.269 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.049 _exptl_crystal_recrystallization_method 'cooled sat. soln. in 1:1 MeOH/2-BuOH to -12 deg. C for several days' _diffrn_ambient_pressure 101.33 #===END data_dpacod _database_code_depnum_ccdc_archive 'CCDC 698583' _audit_creation_method SHELXL-97 _chemical_name_systematic "(2,2'-dipyridylamine)(\h4-1,5-cyclooctadiene)copper(I) tetrafluoroborate" _chemical_name_common ;(2,2'-dipyridylamine)(eta4-1,5-cyclooctadiene)copper(i) tetrafluoroborate ; _chemical_melting_point 455 _chemical_formula_moiety 'C18 H21 Cu N3, B F4' _chemical_formula_sum 'C18 H21 B Cu F4 N3' _chemical_formula_weight 429.73 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' 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_int_tables_number 11 _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.2165(14) _cell_length_b 11.797(2) _cell_length_c 10.771(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.30(3) _cell_angle_gamma 90.00 _cell_volume 913.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2043 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 22.23 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7123 _exptl_absorpt_correction_T_max 0.7848 _exptl_absorpt_process_details 'SADABS v2.10 (Bruker-AXS, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker SMART CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7472 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2289 _reflns_number_gt 1699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.630 (Bruker-AXS 2003)' _computing_cell_refinement 'SMART v5.630 (Bruker-AXS 2003)' _computing_data_reduction 'Bruker SAINT+ v6.45 (Bruker-AXS 2003)' _computing_structure_solution 'SHELXTL v5.1 (Bruker-AXS, 1998)' _computing_structure_refinement 'SHELXTL v5.1' _computing_molecular_graphics 'SHELXTL v5.1' _computing_publication_material 'SHELXTL v5.1' _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. Only fluorines F(1) through F(4) are present in the asymmetric unit of the complex. Disordered atoms F(1)-F(4) were refined with 50 % site occupancies, as B(1) lies on a mirror plane. For initial refinement cycles, similar distance restraints (SADI) were placed on all B-F and F-F distances, in addition to similar ADP restraints (SIMU) and rigid bond restraints (DELU) for all F atoms. Restraints were lifted for final refinement cycles. ; _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^)+(0.0977P)^2^+1.5308P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.034(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2289 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1990 _refine_ls_wR_factor_gt 0.1796 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.55363(10) 0.7500 0.70491(7) 0.0544(3) Uani 1 2 d S . . N1 N 0.3461(7) 0.7500 0.9494(5) 0.0544(12) Uani 1 2 d S . . H1A H 0.3399 0.7500 1.0288 0.065 Uiso 1 2 calc SR . . N2 N 0.4367(4) 0.6250(3) 0.7951(3) 0.0465(7) Uani 1 1 d . . . C1 C 0.3501(5) 0.6436(3) 0.8982(3) 0.0444(8) Uani 1 1 d . . . C2 C 0.2636(6) 0.5551(4) 0.9583(4) 0.0578(11) Uani 1 1 d . . . H2A H 0.2073 0.5689 1.0310 0.069 Uiso 1 1 calc R . . C3 C 0.2632(7) 0.4487(4) 0.9084(5) 0.0680(13) Uani 1 1 d . . . H3A H 0.2048 0.3894 0.9463 0.082 Uiso 1 1 calc R . . C4 C 0.3499(8) 0.4298(4) 0.8017(5) 0.0690(13) Uani 1 1 d . . . H4A H 0.3507 0.3578 0.7664 0.083 Uiso 1 1 calc R . . C5 C 0.4339(7) 0.5178(4) 0.7491(5) 0.0603(11) Uani 1 1 d . . . H5A H 0.4931 0.5041 0.6775 0.072 Uiso 1 1 calc R . . C6 C 0.6358(6) 0.6924(4) 0.5351(4) 0.0543(10) Uani 1 1 d . . . H6A H 0.5328 0.6601 0.4807 0.065 Uiso 1 1 calc R . . C7 C 0.8033(8) 0.6162(5) 0.5503(5) 0.0783(15) Uani 1 1 d . . . H7A H 0.7590 0.5387 0.5415 0.094 Uiso 1 1 calc R . . H7B H 0.8766 0.6310 0.4810 0.094 Uiso 1 1 calc R . . C8 C 0.9280(12) 0.6218(8) 0.6637(11) 0.183(6) Uani 1 1 d . . . H8A H 0.9395 0.5453 0.6964 0.219 Uiso 1 1 calc R . . H8B H 1.0495 0.6427 0.6391 0.219 Uiso 1 1 calc R . . C9 C 0.8926(7) 0.6938(6) 0.7656(5) 0.090(2) Uani 1 1 d . . . H9A H 0.8670 0.6583 0.8392 0.108 Uiso 1 1 calc R . . B1 B 0.1523(12) 0.7500 1.2762(8) 0.0640(19) Uani 1 2 d S . . F1 F 0.1935(16) 0.6583(10) 1.3397(16) 0.195(8) Uani 0.50 1 d P . . F2 F 0.2944(17) 0.8047(15) 1.2594(16) 0.246(11) Uani 0.50 1 d P . . F3 F 0.004(2) 0.7803(18) 1.3107(13) 0.239(11) Uani 0.50 1 d P . . F4 F 0.0913(19) 0.770(2) 1.1526(11) 0.216(9) Uani 0.50 1 d P . . 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 0.0648(5) 0.0471(5) 0.0550(5) 0.000 0.0256(3) 0.000 N1 0.062(3) 0.059(3) 0.045(2) 0.000 0.017(2) 0.000 N2 0.0506(18) 0.0441(18) 0.0458(16) 0.0001(14) 0.0107(13) -0.0008(14) C1 0.0363(17) 0.053(2) 0.0440(18) 0.0084(16) 0.0027(13) 0.0009(15) C2 0.050(2) 0.069(3) 0.056(2) 0.016(2) 0.0087(17) -0.002(2) C3 0.064(3) 0.057(3) 0.083(3) 0.024(2) 0.001(2) -0.010(2) C4 0.085(3) 0.043(2) 0.079(3) 0.004(2) 0.006(3) -0.006(2) C5 0.075(3) 0.045(2) 0.063(3) -0.004(2) 0.014(2) -0.003(2) C6 0.059(2) 0.067(3) 0.0375(18) -0.0099(17) 0.0059(16) -0.003(2) C7 0.089(4) 0.074(3) 0.078(3) -0.004(3) 0.038(3) 0.017(3) C8 0.119(6) 0.135(8) 0.272(13) -0.110(9) -0.107(8) 0.077(6) C9 0.053(3) 0.140(6) 0.072(3) 0.047(3) -0.014(2) -0.008(3) B1 0.066(5) 0.065(5) 0.064(4) 0.000 0.021(4) 0.000 F1 0.117(8) 0.152(10) 0.327(19) 0.172(12) 0.077(10) 0.051(7) F2 0.135(8) 0.32(3) 0.274(16) 0.152(16) -0.029(9) -0.138(13) F3 0.215(12) 0.30(3) 0.216(12) 0.079(14) 0.108(10) 0.196(17) F4 0.254(14) 0.25(2) 0.148(8) 0.100(14) 0.043(9) 0.141(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.996(3) . ? Cu1 N2 1.996(3) 4_575 ? Cu1 C6 2.087(4) 4_575 ? Cu1 C6 2.087(4) . ? Cu1 C9 2.560(5) 4_575 ? Cu1 C9 2.560(5) . ? N1 C1 1.373(5) . ? N1 C1 1.373(5) 4_575 ? N1 H1A 0.8600 . ? N2 C1 1.341(5) . ? N2 C5 1.358(6) . ? C1 C2 1.404(6) . ? C2 C3 1.365(7) . ? C2 H2A 0.9300 . ? C3 C4 1.377(8) . ? C3 H3A 0.9300 . ? C4 C5 1.353(7) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C6 1.358(10) 4_575 ? C6 C7 1.503(7) . ? C6 H6A 0.9800 . ? C7 C8 1.450(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.430(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C9 1.325(15) 4_575 ? C9 H9A 0.9300 . ? B1 F3 1.222(12) 4_575 ? B1 F3 1.222(12) . ? B1 F2 1.239(12) . ? B1 F2 1.239(12) 4_575 ? B1 F1 1.300(10) 4_575 ? B1 F1 1.300(10) . ? B1 F4 1.383(13) 4_575 ? B1 F4 1.383(13) . ? F1 F2 1.26(2) 4_575 ? F1 F3 1.56(2) 4_575 ? F2 F1 1.26(2) 4_575 ? F2 F2 1.29(4) 4_575 ? F3 F3 0.72(4) 4_575 ? F3 F1 1.56(2) 4_575 ? F4 F4 0.46(5) 4_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 95.27(19) . 4_575 ? N2 Cu1 C6 146.53(17) . 4_575 ? N2 Cu1 C6 110.70(16) 4_575 4_575 ? N2 Cu1 C6 110.70(16) . . ? N2 Cu1 C6 146.53(17) 4_575 . ? C6 Cu1 C6 38.0(3) 4_575 . ? N2 Cu1 C9 120.26(19) . 4_575 ? N2 Cu1 C9 96.98(16) 4_575 4_575 ? C6 Cu1 C9 88.05(17) . 4_575 ? C6 Cu1 C9 78.32(19) 4_575 4_575 ? N2 Cu1 C9 96.98(16) . . ? N2 Cu1 C9 120.26(19) 4_575 . ? C6 Cu1 C9 78.32(19) . . ? C6 Cu1 C9 88.05(17) 4_575 . ? C9 Cu1 C9 30.0(3) 4_575 . ? C1 N1 C1 132.3(5) . 4_575 ? C1 N1 H1A 113.9 . . ? C1 N1 H1A 113.9 4_575 . ? C1 N2 C5 117.5(4) . . ? C1 N2 Cu1 122.2(3) . . ? C5 N2 Cu1 120.2(3) . . ? N2 C1 N1 120.7(4) . . ? N2 C1 C2 121.4(4) . . ? N1 C1 C2 117.9(4) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 119.5(4) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 118.7(5) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 N2 123.7(4) . . ? C4 C5 H5A 118.2 . . ? N2 C5 H5A 118.2 . . ? C6 C6 C7 126.8(3) 4_575 . ? C6 C6 Cu1 71.02(13) 4_575 . ? C7 C6 Cu1 112.9(3) . . ? C6 C6 H6A 112.9 4_575 . ? C7 C6 H6A 112.9 . . ? Cu1 C6 H6A 112.9 . . ? C8 C7 C6 119.6(5) . . ? C8 C7 H7A 107.4 . . ? C6 C7 H7A 107.4 . . ? C8 C7 H7B 107.4 . . ? C6 C7 H7B 107.4 . . ? H7A C7 H7B 106.9 . . ? C9 C8 C7 122.2(6) . . ? C9 C8 H8A 106.8 . . ? C7 C8 H8A 106.8 . . ? C9 C8 H8B 106.8 . . ? C7 C8 H8B 106.8 . . ? H8A C8 H8B 106.6 . . ? C9 C9 C8 126.4(6) 4_575 . ? C9 C9 Cu1 75.00(16) 4_575 . ? C8 C9 Cu1 101.1(4) . . ? C9 C9 H9A 116.8 4_575 . ? C8 C9 H9A 116.8 . . ? Cu1 C9 H9A 94.2 . . ? F3 B1 F2 130.9(14) . . ? F3 B1 F1 104.4(11) . . ? F2 B1 F1 111.0(12) . . ? F3 B1 F4 91.9(10) . . ? F2 B1 F4 88.0(11) . . ? F1 B1 F4 133.1(14) . . ? F2 F1 B1 57.9(8) 4_575 . ? F2 F1 F3 104.8(10) 4_575 4_575 ? B1 F1 F3 49.7(7) . 4_575 ? B1 F2 F1 62.7(7) . 4_575 ? B1 F2 F2 58.6(10) . 4_575 ? F1 F2 F2 110.3(10) 4_575 4_575 ? F3 F3 B1 73.0(10) 4_575 . ? F3 F3 F1 117.7(8) 4_575 4_575 ? B1 F3 F1 54.2(8) . 4_575 ? F4 F4 B1 80.3(11) 4_575 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N2 C1 -12.4(4) 4_575 . . . ? C6 Cu1 N2 C1 -154.0(3) 4_575 . . . ? C6 Cu1 N2 C1 -170.9(3) . . . . ? C9 Cu1 N2 C1 88.8(3) 4_575 . . . ? C9 Cu1 N2 C1 109.0(3) . . . . ? N2 Cu1 N2 C5 164.0(3) 4_575 . . . ? C6 Cu1 N2 C5 22.4(5) 4_575 . . . ? C6 Cu1 N2 C5 5.5(4) . . . . ? C9 Cu1 N2 C5 -94.8(4) 4_575 . . . ? C9 Cu1 N2 C5 -74.6(4) . . . . ? C5 N2 C1 N1 -179.5(4) . . . . ? Cu1 N2 C1 N1 -3.0(5) . . . . ? C5 N2 C1 C2 1.5(6) . . . . ? Cu1 N2 C1 C2 178.0(3) . . . . ? C1 N1 C1 N2 29.1(9) 4_575 . . . ? C1 N1 C1 C2 -151.9(5) 4_575 . . . ? N2 C1 C2 C3 -1.9(6) . . . . ? N1 C1 C2 C3 179.1(4) . . . . ? C1 C2 C3 C4 1.0(7) . . . . ? C2 C3 C4 C5 0.1(8) . . . . ? C3 C4 C5 N2 -0.5(8) . . . . ? C1 N2 C5 C4 -0.3(7) . . . . ? Cu1 N2 C5 C4 -176.9(4) . . . . ? N2 Cu1 C6 C6 164.84(14) . . . 4_575 ? N2 Cu1 C6 C6 26.3(2) 4_575 . . 4_575 ? N2 Cu1 C6 C7 -72.4(4) . . . . ? N2 Cu1 C6 C7 149.1(3) 4_575 . . . ? C6 Cu1 C6 C7 122.8(4) 4_575 . . . ? C6 C6 C7 C8 60.6(8) 4_575 . . . ? Cu1 C6 C7 C8 -22.2(9) . . . . ? C6 C7 C8 C9 3.3(14) . . . . ? C7 C8 C9 C9 -66.6(12) . . . 4_575 ? F3 B1 F1 F2 158.2(14) 4_575 . . 4_575 ? F3 B1 F1 F2 177.4(15) . . . 4_575 ? F2 B1 F1 F2 -37.2(16) . . . 4_575 ? F1 B1 F1 F2 -101.8(15) 4_575 . . 4_575 ? F4 B1 F1 F2 72.3(12) 4_575 . . 4_575 ? F4 B1 F1 F2 70.8(15) . . . 4_575 ? F3 B1 F1 F3 19.3(13) . . . 4_575 ? F2 B1 F1 F3 164.6(14) . . . 4_575 ? F2 B1 F1 F3 -158.2(14) 4_575 . . 4_575 ? F1 B1 F1 F3 100.0(11) 4_575 . . 4_575 ? F4 B1 F1 F3 -85.9(11) 4_575 . . 4_575 ? F4 B1 F1 F3 -87.4(15) . . . 4_575 ? F3 B1 F2 F1 9(5) 4_575 . . 4_575 ? F3 B1 F2 F1 28.5(18) . . . 4_575 ? F2 B1 F2 F1 -140.6(11) 4_575 . . 4_575 ? F1 B1 F2 F1 -105(2) . . . 4_575 ? F4 B1 F2 F1 135.9(15) 4_575 . . 4_575 ? F4 B1 F2 F1 119.3(14) . . . 4_575 ? F3 B1 F2 F2 149(5) 4_575 . . 4_575 ? F3 B1 F2 F2 169.1(18) . . . 4_575 ? F1 B1 F2 F2 140.6(11) 4_575 . . 4_575 ? F1 B1 F2 F2 35.9(10) . . . 4_575 ? F4 B1 F2 F2 -83.6(12) 4_575 . . 4_575 ? F4 B1 F2 F2 -100.1(10) . . . 4_575 ? F2 B1 F3 F3 -170.3(16) . . . 4_575 ? F2 B1 F3 F3 -27(5) 4_575 . . 4_575 ? F1 B1 F3 F3 -145.2(10) 4_575 . . 4_575 ? F1 B1 F3 F3 -34.9(9) . . . 4_575 ? F4 B1 F3 F3 82.1(10) 4_575 . . 4_575 ? F4 B1 F3 F3 100.7(11) . . . 4_575 ? F3 B1 F3 F1 145.2(10) 4_575 . . 4_575 ? F2 B1 F3 F1 -25.0(16) . . . 4_575 ? F2 B1 F3 F1 118(5) 4_575 . . 4_575 ? F1 B1 F3 F1 110.3(19) . . . 4_575 ? F4 B1 F3 F1 -132.7(14) 4_575 . . 4_575 ? F4 B1 F3 F1 -114.1(14) . . . 4_575 ? F3 B1 F4 F4 -73.9(10) 4_575 . . 4_575 ? F3 B1 F4 F4 -107.6(11) . . . 4_575 ? F2 B1 F4 F4 121.5(10) . . . 4_575 ? F2 B1 F4 F4 59.4(9) 4_575 . . 4_575 ? F1 B1 F4 F4 176.7(9) 4_575 . . 4_575 ? F1 B1 F4 F4 4.2(11) . . . 4_575 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A F4 0.86 2.34 2.995(13) 132.7 . _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.456 _refine_diff_density_min -0.955 _refine_diff_density_rms 0.090 _exptl_crystal_recrystallization_method 'cooled sat. soln in MeOH to -12 deg. C for several days' _diffrn_ambient_pressure 101.33