# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Robert Pike' _publ_contact_author_email RDPIKE@WM.EDU _publ_section_title ; Reversible Luminescent Reaction of Amines with Copper(I) Cyanide ; loop_ _publ_author_name 'Robert Pike' 'Francois Baril-Robert' 'Timothy P. Brewster' 'Matthew D. Dembo' 'Lars E. Dunaway' ; T.D.Harris ; 'Amanda N. Ley' 'Xiaobo Li.' 'Howard H. Patterson' data_c2onc _database_code_depnum_ccdc_archive 'CCDC 743724' #TrackingRef 'RDP_CuCN_Amines_Structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H44 Cu3 N7' _chemical_formula_sum 'C23 H44 Cu3 N7' _chemical_formula_weight 609.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _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 26.3331(2) _cell_length_b 5.22920(10) _cell_length_c 23.7064(2) _cell_angle_alpha 90.00 _cell_angle_beta 122.6785(3) _cell_angle_gamma 90.00 _cell_volume 2747.68(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8791 _cell_measurement_theta_min 3.99 _cell_measurement_theta_max 68.24 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 2.870 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5458 _exptl_absorpt_correction_T_max 0.9188 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14544 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 66.98 _reflns_number_total 2413 _reflns_number_gt 2271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0372P)^2^+2.4013P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2413 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0594 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.031969(10) 1.15660(5) 0.082760(11) 0.02174(9) Uani 1 1 d . . . Cu2 Cu 0.0000 0.74075(6) 0.2500 0.01956(10) Uani 1 2 d S . . N1 N 0.00780(6) 1.4185(3) 0.01960(7) 0.0211(3) Uani 0.50 1 d P . . C1 C 0.00780(6) 1.4185(3) 0.01960(7) 0.0211(3) Uani 0.50 1 d P . . N2A N 0.01766(6) 1.0095(3) 0.14605(7) 0.0224(4) Uani 0.618(18) 1 d P A 1 C2A C 0.01250(6) 0.9095(3) 0.18654(7) 0.0201(4) Uani 0.618(18) 1 d P A 1 C2B C 0.01766(6) 1.0095(3) 0.14605(7) 0.0224(4) Uani 0.382(18) 1 d P A 2 N2B N 0.01250(6) 0.9095(3) 0.18654(7) 0.0201(4) Uani 0.382(18) 1 d P A 2 N3 N 0.10508(6) 0.9210(3) 0.09847(6) 0.0171(3) Uani 1 1 d . A . N4 N 0.06944(5) 0.4554(3) 0.30825(6) 0.0159(3) Uani 1 1 d . A . C3 C 0.12757(7) 0.9502(3) 0.05353(8) 0.0230(3) Uani 1 1 d . . . C4 C 0.15720(8) 1.2087(3) 0.06378(8) 0.0233(3) Uani 1 1 d . A . C5 C 0.20774(7) 1.2460(3) 0.13686(9) 0.0251(4) Uani 1 1 d . . . C6 C 0.18496(7) 1.1955(4) 0.18288(8) 0.0245(4) Uani 1 1 d . A . C7 C 0.15548(7) 0.9344(3) 0.16927(8) 0.0216(3) Uani 1 1 d . . . C8 C 0.11360(7) 0.4296(3) 0.28840(8) 0.0184(3) Uani 1 1 d . . . C9 C 0.15894(8) 0.2161(3) 0.32576(8) 0.0240(3) Uani 1 1 d . A . C10 C 0.19148(7) 0.2502(3) 0.40141(8) 0.0240(4) Uani 1 1 d . . . C11 C 0.14580(7) 0.2802(3) 0.42176(8) 0.0222(3) Uani 1 1 d . A . C12 C 0.10042(7) 0.4910(3) 0.38154(7) 0.0199(3) Uani 1 1 d . . . H3N H 0.0897(8) 0.784(4) 0.0938(8) 0.011(4) Uiso 1 1 d . . . H4N H 0.0508(8) 0.311(4) 0.2983(9) 0.016(4) Uiso 1 1 d . . . H3A H 0.0946(10) 0.932(4) 0.0104(11) 0.034(5) Uiso 1 1 d . . . H3B H 0.1565(8) 0.811(4) 0.0620(9) 0.020(4) Uiso 1 1 d . . . H4A H 0.1736(9) 1.214(4) 0.0356(10) 0.028(5) Uiso 1 1 d . . . H4B H 0.1271(9) 1.337(4) 0.0498(9) 0.019(4) Uiso 1 1 d . . . H5A H 0.2238(9) 1.418(4) 0.1438(10) 0.032(5) Uiso 1 1 d . . . H5B H 0.2408(9) 1.125(4) 0.1472(10) 0.027(5) Uiso 1 1 d . . . H6A H 0.2166(9) 1.201(4) 0.2280(11) 0.026(5) Uiso 1 1 d . . . H6B H 0.1572(9) 1.328(4) 0.1778(9) 0.023(5) Uiso 1 1 d . . . H7A H 0.1405(8) 0.907(4) 0.1968(10) 0.023(5) Uiso 1 1 d . . . H7B H 0.1848(9) 0.801(4) 0.1775(10) 0.030(5) Uiso 1 1 d . . . H8A H 0.0921(8) 0.397(4) 0.2413(10) 0.019(4) Uiso 1 1 d . . . H8B H 0.1337(8) 0.584(4) 0.2984(8) 0.013(4) Uiso 1 1 d . . . H9A H 0.1871(10) 0.207(4) 0.3111(10) 0.033(5) Uiso 1 1 d . . . H9B H 0.1373(9) 0.062(4) 0.3115(10) 0.029(5) Uiso 1 1 d . . . H10A H 0.2180(9) 0.106(4) 0.4232(10) 0.028(5) Uiso 1 1 d . . . H10B H 0.2165(8) 0.407(4) 0.4147(9) 0.021(5) Uiso 1 1 d . . . H11A H 0.1654(9) 0.317(4) 0.4674(11) 0.025(5) Uiso 1 1 d . . . H11B H 0.1244(10) 0.129(4) 0.4132(10) 0.030(5) Uiso 1 1 d . . . H12A H 0.0707(8) 0.501(4) 0.3924(9) 0.024(5) Uiso 1 1 d . . . H12B H 0.1202(8) 0.656(4) 0.3923(9) 0.018(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01595(14) 0.02514(16) 0.01884(14) 0.00451(9) 0.00592(11) -0.00105(9) Cu2 0.01633(17) 0.01665(18) 0.02038(18) 0.000 0.00642(14) 0.000 N1 0.0156(7) 0.0260(8) 0.0177(7) -0.0001(5) 0.0065(6) -0.0040(6) C1 0.0156(7) 0.0260(8) 0.0177(7) -0.0001(5) 0.0065(6) -0.0040(6) N2A 0.0178(7) 0.0227(8) 0.0245(8) 0.0024(6) 0.0100(6) 0.0018(6) C2A 0.0155(7) 0.0196(8) 0.0224(8) -0.0006(6) 0.0084(6) 0.0004(6) C2B 0.0178(7) 0.0227(8) 0.0245(8) 0.0024(6) 0.0100(6) 0.0018(6) N2B 0.0155(7) 0.0196(8) 0.0224(8) -0.0006(6) 0.0084(6) 0.0004(6) N3 0.0166(6) 0.0174(7) 0.0144(6) -0.0009(5) 0.0063(5) -0.0041(5) N4 0.0150(6) 0.0166(7) 0.0144(6) 0.0002(5) 0.0069(5) -0.0008(5) C3 0.0235(8) 0.0296(9) 0.0165(8) -0.0059(6) 0.0111(7) -0.0044(7) C4 0.0236(8) 0.0269(9) 0.0242(8) 0.0024(7) 0.0162(7) -0.0015(7) C5 0.0189(8) 0.0266(9) 0.0304(9) -0.0066(7) 0.0138(7) -0.0064(7) C6 0.0169(8) 0.0334(10) 0.0177(8) -0.0085(7) 0.0058(7) -0.0058(7) C7 0.0165(8) 0.0286(9) 0.0144(7) 0.0036(6) 0.0050(6) 0.0019(6) C8 0.0192(8) 0.0211(8) 0.0152(8) 0.0008(6) 0.0096(6) 0.0021(6) C9 0.0228(8) 0.0277(9) 0.0206(8) -0.0001(7) 0.0110(7) 0.0079(7) C10 0.0175(8) 0.0300(10) 0.0182(8) 0.0040(7) 0.0054(7) 0.0054(7) C11 0.0228(8) 0.0265(9) 0.0142(8) 0.0032(6) 0.0079(7) 0.0001(7) C12 0.0224(8) 0.0238(9) 0.0146(7) 0.0007(6) 0.0108(6) 0.0030(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 N1 1.8691(15) . ? Cu1 N2A 1.8962(15) . ? Cu1 N3 2.1421(13) . ? Cu2 N2B 1.9196(15) 2 ? Cu2 C2A 1.9196(15) 2 ? Cu2 C2A 1.9197(15) . ? Cu2 N4 2.1795(13) 2 ? Cu2 N4 2.1795(13) . ? N1 C1 1.161(3) 5_585 ? N1 N1 1.161(3) 5_585 ? N2A C2A 1.164(2) . ? N3 C7 1.4757(19) . ? N3 C3 1.480(2) . ? N3 H3N 0.80(2) . ? N4 C12 1.4791(19) . ? N4 C8 1.4775(19) . ? N4 H4N 0.86(2) . ? C3 C4 1.513(2) . ? C3 H3A 0.92(2) . ? C3 H3B 0.99(2) . ? C4 C5 1.523(2) . ? C4 H4A 0.97(2) . ? C4 H4B 0.95(2) . ? C5 C6 1.525(2) . ? C5 H5A 0.97(2) . ? C5 H5B 0.99(2) . ? C6 C7 1.517(2) . ? C6 H6A 0.94(2) . ? C6 H6B 0.97(2) . ? C7 H7A 0.94(2) . ? C7 H7B 0.98(2) . ? C8 C9 1.521(2) . ? C8 H8A 0.96(2) . ? C8 H8B 0.922(19) . ? C9 C10 1.524(2) . ? C9 H9A 0.98(2) . ? C9 H9B 0.94(2) . ? C10 C11 1.526(2) . ? C10 H10A 0.97(2) . ? C10 H10B 0.99(2) . ? C11 C12 1.524(2) . ? C11 H11A 0.93(2) . ? C11 H11B 0.93(2) . ? C12 H12A 0.948(19) . ? C12 H12B 0.97(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2A 143.51(6) . . ? N1 Cu1 N3 116.48(6) . . ? N2A Cu1 N3 99.97(6) . . ? N2B Cu2 C2A 0.00(10) 2 2 ? N2B Cu2 C2A 125.27(9) 2 . ? C2A Cu2 C2A 125.27(9) 2 . ? N2B Cu2 N4 111.78(5) 2 2 ? C2A Cu2 N4 111.78(5) 2 2 ? C2A Cu2 N4 104.97(5) . 2 ? N2B Cu2 N4 104.97(5) 2 . ? C2A Cu2 N4 104.97(5) 2 . ? C2A Cu2 N4 111.78(5) . . ? N4 Cu2 N4 93.60(7) 2 . ? C1 N1 Cu1 179.19(18) 5_585 . ? N1 N1 Cu1 179.19(18) 5_585 . ? C2A N2A Cu1 175.28(13) . . ? N2A C2A Cu2 177.22(14) . . ? C7 N3 C3 110.50(12) . . ? C7 N3 Cu1 110.03(10) . . ? C3 N3 Cu1 119.13(10) . . ? C7 N3 H3N 106.1(12) . . ? C3 N3 H3N 111.2(12) . . ? Cu1 N3 H3N 98.6(12) . . ? C12 N4 C8 110.84(12) . . ? C12 N4 Cu2 113.59(9) . . ? C8 N4 Cu2 113.34(9) . . ? C12 N4 H4N 107.6(12) . . ? C8 N4 H4N 105.3(12) . . ? Cu2 N4 H4N 105.5(12) . . ? N3 C3 C4 110.40(13) . . ? N3 C3 H3A 106.6(12) . . ? C4 C3 H3A 111.5(14) . . ? N3 C3 H3B 109.9(11) . . ? C4 C3 H3B 110.4(11) . . ? H3A C3 H3B 107.9(17) . . ? C3 C4 C5 110.78(14) . . ? C3 C4 H4A 107.3(12) . . ? C5 C4 H4A 109.8(12) . . ? C3 C4 H4B 108.4(11) . . ? C5 C4 H4B 110.9(11) . . ? H4A C4 H4B 109.6(16) . . ? C4 C5 C6 110.60(13) . . ? C4 C5 H5A 110.2(12) . . ? C6 C5 H5A 110.0(12) . . ? C4 C5 H5B 108.0(11) . . ? C6 C5 H5B 110.1(11) . . ? H5A C5 H5B 107.9(17) . . ? C7 C6 C5 110.93(14) . . ? C7 C6 H6A 108.0(12) . . ? C5 C6 H6A 111.1(12) . . ? C7 C6 H6B 110.7(12) . . ? C5 C6 H6B 110.5(11) . . ? H6A C6 H6B 105.5(17) . . ? N3 C7 C6 109.10(13) . . ? N3 C7 H7A 109.0(12) . . ? C6 C7 H7A 110.4(12) . . ? N3 C7 H7B 108.8(12) . . ? C6 C7 H7B 110.0(12) . . ? H7A C7 H7B 109.5(17) . . ? N4 C8 C9 112.76(13) . . ? N4 C8 H8A 108.5(11) . . ? C9 C8 H8A 109.4(11) . . ? N4 C8 H8B 106.2(10) . . ? C9 C8 H8B 109.3(11) . . ? H8A C8 H8B 110.7(15) . . ? C8 C9 C10 111.41(14) . . ? C8 C9 H9A 109.8(13) . . ? C10 C9 H9A 111.9(12) . . ? C8 C9 H9B 106.8(13) . . ? C10 C9 H9B 111.7(12) . . ? H9A C9 H9B 104.9(17) . . ? C9 C10 C11 110.22(13) . . ? C9 C10 H10A 108.7(12) . . ? C11 C10 H10A 112.2(11) . . ? C9 C10 H10B 109.0(11) . . ? C11 C10 H10B 108.5(10) . . ? H10A C10 H10B 108.1(16) . . ? C12 C11 C10 111.24(13) . . ? C12 C11 H11A 109.4(12) . . ? C10 C11 H11A 110.5(12) . . ? C12 C11 H11B 107.6(13) . . ? C10 C11 H11B 109.3(13) . . ? H11A C11 H11B 108.7(17) . . ? N4 C12 C11 113.14(13) . . ? N4 C12 H12A 108.2(11) . . ? C11 C12 H12A 110.8(12) . . ? N4 C12 H12B 107.4(11) . . ? C11 C12 H12B 110.6(11) . . ? H12A C12 H12B 106.4(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N3 C7 120.90(11) . . . . ? N2A Cu1 N3 C7 -57.36(11) . . . . ? N1 Cu1 N3 C3 -8.14(13) . . . . ? N2A Cu1 N3 C3 173.60(11) . . . . ? N2B Cu2 N4 C12 -13.06(11) 2 . . . ? C2A Cu2 N4 C12 -13.06(11) 2 . . . ? C2A Cu2 N4 C12 125.57(11) . . . . ? N4 Cu2 N4 C12 -126.74(11) 2 . . . ? N2B Cu2 N4 C8 -140.73(10) 2 . . . ? C2A Cu2 N4 C8 -140.73(10) 2 . . . ? C2A Cu2 N4 C8 -2.10(12) . . . . ? N4 Cu2 N4 C8 105.58(11) 2 . . . ? C7 N3 C3 C4 -61.71(18) . . . . ? Cu1 N3 C3 C4 67.11(15) . . . . ? N3 C3 C4 C5 56.33(18) . . . . ? C3 C4 C5 C6 -52.54(19) . . . . ? C4 C5 C6 C7 53.89(19) . . . . ? C3 N3 C7 C6 62.25(17) . . . . ? Cu1 N3 C7 C6 -71.34(14) . . . . ? C5 C6 C7 N3 -58.38(18) . . . . ? C12 N4 C8 C9 55.28(18) . . . . ? Cu2 N4 C8 C9 -175.63(11) . . . . ? N4 C8 C9 C10 -55.39(19) . . . . ? C8 C9 C10 C11 53.3(2) . . . . ? C9 C10 C11 C12 -52.73(19) . . . . ? C8 N4 C12 C11 -55.01(17) . . . . ? Cu2 N4 C12 C11 176.03(10) . . . . ? C10 C11 C12 N4 54.53(19) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.529 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.048 data_p212121a _database_code_depnum_ccdc_archive 'CCDC 743725' #TrackingRef 'RDP_CuCN_Amines_Structures.cif' #TrackingRef 'RDP_CuCN_Amines_Structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 Cu N2' _chemical_formula_sum 'C9 H17 Cu N2' _chemical_formula_weight 216.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.31450(10) _cell_length_b 9.34500(10) _cell_length_c 17.4458(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1029.46(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9531 _cell_measurement_theta_min 4.73 _cell_measurement_theta_max 67.47 _exptl_crystal_description flake _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 2.579 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5427 _exptl_absorpt_correction_T_max 0.7576 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_reflns_number 10747 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.07 _diffrn_reflns_theta_max 67.00 _reflns_number_total 1814 _reflns_number_gt 1806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0235P)^2^+0.1967P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.53(2) _refine_ls_number_reflns 1814 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0165 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0440 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.002 _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 0.08021(3) 1.01952(2) 0.783427(11) 0.01588(8) Uani 1 1 d . . . C1A C 0.0115(2) 1.21190(15) 0.76300(7) 0.0176(4) Uani 0.49(2) 1 d P . 1 N1A N 0.0200(2) 0.82897(16) 0.75497(8) 0.0186(4) Uani 0.49(2) 1 d P . 1 N1B N 0.0115(2) 1.21190(15) 0.76300(7) 0.0176(4) Uani 0.51(2) 1 d P . 2 C1B C 0.0200(2) 0.82897(16) 0.75497(8) 0.0186(4) Uani 0.51(2) 1 d P . 2 N2 N 0.35628(18) 1.01288(14) 0.85899(7) 0.0158(2) Uani 1 1 d . . . C2 C 0.4562(3) 1.15507(19) 0.85980(10) 0.0264(4) Uani 1 1 d . . . H2A H 0.5884 1.1508 0.8891 0.040 Uiso 1 1 calc R . . H2B H 0.3599 1.2242 0.8837 0.040 Uiso 1 1 calc R . . H2C H 0.4869 1.1850 0.8071 0.040 Uiso 1 1 calc R . . C3 C 0.5040(3) 0.9102(2) 0.82320(9) 0.0241(4) Uani 1 1 d . . . H3A H 0.5337 0.9400 0.7704 0.036 Uiso 1 1 calc R . . H3B H 0.4399 0.8147 0.8229 0.036 Uiso 1 1 calc R . . H3C H 0.6364 0.9077 0.8525 0.036 Uiso 1 1 calc R . . C4 C 0.2926(2) 0.96137(16) 0.93692(8) 0.0147(3) Uani 1 1 d . . . H4 H 0.2499 0.8589 0.9311 0.018 Uiso 1 1 calc R . . C5 C 0.0993(2) 1.04148(16) 0.96699(8) 0.0185(3) Uani 1 1 d . . . H5A H -0.0166 1.0358 0.9289 0.022 Uiso 1 1 calc R . . H5B H 0.1354 1.1436 0.9744 0.022 Uiso 1 1 calc R . . C6 C 0.0244(2) 0.97727(19) 1.04334(8) 0.0200(3) Uani 1 1 d . . . H6A H -0.0976 1.0330 1.0628 0.024 Uiso 1 1 calc R . . H6B H -0.0233 0.8776 1.0349 0.024 Uiso 1 1 calc R . . C7 C 0.2015(2) 0.97852(19) 1.10295(8) 0.0210(3) Uani 1 1 d . . . H7A H 0.2388 1.0787 1.1156 0.025 Uiso 1 1 calc R . . H7B H 0.1517 0.9313 1.1504 0.025 Uiso 1 1 calc R . . C8 C 0.3965(3) 0.90125(18) 1.07294(8) 0.0216(3) Uani 1 1 d . . . H8A H 0.3631 0.7986 1.0657 0.026 Uiso 1 1 calc R . . H8B H 0.5119 0.9084 1.1112 0.026 Uiso 1 1 calc R . . C9 C 0.4713(2) 0.96518(19) 0.99669(8) 0.0187(3) Uani 1 1 d . . . H9A H 0.5943 0.9102 0.9774 0.022 Uiso 1 1 calc R . . H9B H 0.5171 1.0653 1.0048 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01834(11) 0.01405(11) 0.01526(11) 0.00041(8) 0.00013(8) 0.00012(8) C1A 0.0197(7) 0.0171(8) 0.0160(8) -0.0015(5) -0.0003(5) -0.0003(5) N1A 0.0180(7) 0.0194(8) 0.0183(7) 0.0030(6) 0.0003(5) 0.0004(6) N1B 0.0197(7) 0.0171(8) 0.0160(8) -0.0015(5) -0.0003(5) -0.0003(5) C1B 0.0180(7) 0.0194(8) 0.0183(7) 0.0030(6) 0.0003(5) 0.0004(6) N2 0.0161(6) 0.0169(6) 0.0144(5) 0.0025(5) 0.0000(4) -0.0015(5) C2 0.0275(9) 0.0266(9) 0.0252(8) 0.0060(7) -0.0048(7) -0.0120(7) C3 0.0209(8) 0.0332(9) 0.0181(8) 0.0013(7) 0.0021(6) 0.0075(7) C4 0.0151(7) 0.0145(7) 0.0145(7) 0.0003(6) -0.0022(5) -0.0009(6) C5 0.0172(7) 0.0212(7) 0.0172(7) -0.0015(6) -0.0028(6) 0.0015(7) C6 0.0169(7) 0.0254(8) 0.0178(7) -0.0054(7) -0.0003(6) 0.0007(6) C7 0.0221(8) 0.0261(8) 0.0147(6) -0.0027(7) -0.0019(6) -0.0002(7) C8 0.0214(8) 0.0263(8) 0.0171(7) 0.0012(6) -0.0046(6) 0.0028(7) C9 0.0147(7) 0.0239(8) 0.0176(7) 0.0003(6) -0.0028(6) 0.0005(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 C1A 1.8834(14) . ? Cu1 N1A 1.8874(15) . ? Cu1 N2 2.1865(12) . ? C1A N1A 1.155(2) 3_556 ? N1A C1A 1.155(2) 3_546 ? N2 C2 1.471(2) . ? N2 C3 1.477(2) . ? N2 C4 1.4971(17) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.525(2) . ? C4 C9 1.5370(19) . ? C4 H4 1.0000 . ? C5 C6 1.535(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.527(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.520(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.533(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? 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 C1A Cu1 N1A 143.56(6) . . ? C1A Cu1 N2 108.95(6) . . ? N1A Cu1 N2 107.01(6) . . ? N1A C1A Cu1 174.21(13) 3_556 . ? C1A N1A Cu1 178.24(13) 3_546 . ? C2 N2 C3 108.67(13) . . ? C2 N2 C4 113.39(12) . . ? C3 N2 C4 110.16(12) . . ? C2 N2 Cu1 108.80(9) . . ? C3 N2 Cu1 105.49(9) . . ? C4 N2 Cu1 110.03(8) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 111.69(12) . . ? N2 C4 C9 114.30(11) . . ? C5 C4 C9 110.06(12) . . ? N2 C4 H4 106.8 . . ? C5 C4 H4 106.8 . . ? C9 C4 H4 106.8 . . ? C4 C5 C6 110.67(12) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 111.24(12) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 110.79(12) . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 111.30(13) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C4 110.70(12) . . ? C8 C9 H9A 109.5 . . ? C4 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? 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 C1A Cu1 N2 C2 -14.65(11) . . . . ? N1A Cu1 N2 C2 159.32(10) . . . . ? C1A Cu1 N2 C3 -131.09(10) . . . . ? N1A Cu1 N2 C3 42.89(11) . . . . ? C1A Cu1 N2 C4 110.12(10) . . . . ? N1A Cu1 N2 C4 -75.90(10) . . . . ? C2 N2 C4 C5 72.96(15) . . . . ? C3 N2 C4 C5 -165.01(13) . . . . ? Cu1 N2 C4 C5 -49.13(13) . . . . ? C2 N2 C4 C9 -52.80(17) . . . . ? C3 N2 C4 C9 69.22(16) . . . . ? Cu1 N2 C4 C9 -174.90(10) . . . . ? N2 C4 C5 C6 174.62(12) . . . . ? C9 C4 C5 C6 -57.32(16) . . . . ? C4 C5 C6 C7 56.91(17) . . . . ? C5 C6 C7 C8 -55.70(19) . . . . ? C6 C7 C8 C9 55.67(18) . . . . ? C7 C8 C9 C4 -56.70(17) . . . . ? N2 C4 C9 C8 -176.12(13) . . . . ? C5 C4 C9 C8 57.26(17) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.277 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.042 data_ama2 _database_code_depnum_ccdc_archive 'CCDC 743726' #TrackingRef 'RDP_CuCN_Amines_Structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H11 Cu N2 O' _chemical_formula_sum 'C6 H11 Cu N2 O' _chemical_formula_weight 190.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Ama2 _symmetry_space_group_name_Hall 'A 2 -2a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 9.7119(2) _cell_length_b 12.2714(3) _cell_length_c 6.2836(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 748.87(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2749 _cell_measurement_theta_min 7.22 _cell_measurement_theta_max 67.65 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 3.561 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5347 _exptl_absorpt_correction_T_max 0.8147 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 3902 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 7.22 _diffrn_reflns_theta_max 66.82 _reflns_number_total 661 _reflns_number_gt 652 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0183P)^2^+0.2620P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_number_reflns 661 _refine_ls_number_parameters 52 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0180 _refine_ls_R_factor_gt 0.0175 _refine_ls_wR_factor_ref 0.0406 _refine_ls_wR_factor_gt 0.0403 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.7500 0.96028(2) 0.35030(7) 0.01179(12) Uani 1 2 d S . . O1 O 0.7500 0.87749(16) -0.2796(3) 0.0144(4) Uani 1 2 d S . . N1 N 0.94091(16) 0.99411(12) 0.3646(4) 0.0120(3) Uani 0.50 1 d P . . C1 C 0.94091(16) 0.99411(12) 0.3646(4) 0.0120(3) Uani 0.50 1 d P . . N2 N 0.7500 0.80580(17) 0.1562(4) 0.0108(5) Uani 1 2 d S . . C2 C 0.87354(19) 0.79835(14) 0.0194(3) 0.0121(4) Uani 1 1 d . . . H2A H 0.8767 0.7259 -0.0496 0.015 Uiso 1 1 calc R . . H2B H 0.9574 0.8066 0.1075 0.015 Uiso 1 1 calc R . . C3 C 0.87019(15) 0.88712(12) -0.1506(5) 0.0141(3) Uani 1 1 d . . . H3A H 0.8713 0.9596 -0.0814 0.017 Uiso 1 1 calc R . . H3B H 0.9532 0.8812 -0.2413 0.017 Uiso 1 1 calc R . . C4 C 0.7500 0.7149(2) 0.3086(4) 0.0149(7) Uani 1 2 d S . . H4A H 0.7500 0.6457 0.2308 0.022 Uiso 1 2 calc SR . . H4B H 0.6676 0.7192 0.3982 0.022 Uiso 0.50 1 calc PR . . H4C H 0.8324 0.7192 0.3982 0.022 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00776(17) 0.01398(18) 0.01363(18) -0.0010(2) 0.000 0.000 O1 0.0111(9) 0.0227(10) 0.0093(10) 0.0001(8) 0.000 0.000 N1 0.0128(6) 0.0120(6) 0.0113(8) -0.0011(13) 0.0016(12) 0.0000(5) C1 0.0128(6) 0.0120(6) 0.0113(8) -0.0011(13) 0.0016(12) 0.0000(5) N2 0.0095(10) 0.0113(11) 0.0115(13) 0.0004(9) 0.000 0.000 C2 0.0106(8) 0.0133(9) 0.0124(9) -0.0019(8) 0.0021(8) 0.0026(7) C3 0.0117(7) 0.0169(7) 0.0137(8) 0.0002(15) 0.0012(15) 0.0009(6) C4 0.0183(13) 0.0157(12) 0.011(2) 0.0027(10) 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.9021(15) 4_655 ? Cu1 N1 1.9021(15) 4_655 ? Cu1 N1 1.9021(15) . ? Cu1 N2 2.254(2) . ? O1 C3 1.426(3) 4_655 ? O1 C3 1.426(3) . ? N1 C1 1.157(3) 2_775 ? N1 N1 1.157(3) 2_775 ? N2 C4 1.470(3) . ? N2 C2 1.479(2) . ? N2 C2 1.479(2) 4_655 ? C2 C3 1.526(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N1 0.00(16) 4_655 4_655 ? C1 Cu1 N1 154.19(9) 4_655 . ? N1 Cu1 N1 154.19(9) 4_655 . ? C1 Cu1 N2 102.07(6) 4_655 . ? N1 Cu1 N2 102.07(6) 4_655 . ? N1 Cu1 N2 102.07(6) . . ? C3 O1 C3 109.9(3) 4_655 . ? C1 N1 Cu1 173.92(18) 2_775 . ? N1 N1 Cu1 173.92(18) 2_775 . ? C4 N2 C2 109.38(13) . . ? C4 N2 C2 109.38(13) . 4_655 ? C2 N2 C2 108.4(2) . 4_655 ? C4 N2 Cu1 106.61(15) . . ? C2 N2 Cu1 111.51(11) . . ? C2 N2 Cu1 111.51(11) 4_655 . ? N2 C2 C3 110.22(15) . . ? N2 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? O1 C3 C2 110.86(14) . . ? O1 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Cu1 N2 C4 -94.59(8) 4_655 . . . ? N1 Cu1 N2 C4 -94.59(8) 4_655 . . . ? N1 Cu1 N2 C4 94.59(8) . . . . ? C1 Cu1 N2 C2 146.09(14) 4_655 . . . ? N1 Cu1 N2 C2 146.09(14) 4_655 . . . ? N1 Cu1 N2 C2 -24.73(16) . . . . ? C1 Cu1 N2 C2 24.73(16) 4_655 . . 4_655 ? N1 Cu1 N2 C2 24.73(16) 4_655 . . 4_655 ? N1 Cu1 N2 C2 -146.09(14) . . . 4_655 ? C4 N2 C2 C3 175.86(17) . . . . ? C2 N2 C2 C3 56.7(2) 4_655 . . . ? Cu1 N2 C2 C3 -66.48(18) . . . . ? C3 O1 C3 C2 59.8(2) 4_655 . . . ? N2 C2 C3 O1 -59.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.82 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.216 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.056 data_fdd2 _database_code_depnum_ccdc_archive 'CCDC 743727' #TrackingRef 'CCDC743727 RDP229(CuCN)2(4tBuPy)3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H39 Cu2 N5' _chemical_formula_sum 'C29 H39 Cu2 N5' _chemical_formula_weight 584.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.9500(2) _cell_length_b 35.3082(4) _cell_length_c 11.64710(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6148.01(12) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9123 _cell_measurement_theta_min 4.97 _cell_measurement_theta_max 67.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 1.879 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5626 _exptl_absorpt_correction_T_max 0.6982 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 16270 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.97 _diffrn_reflns_theta_max 66.93 _reflns_number_total 2594 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0743P)^2^+2.7608P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(5) _refine_ls_number_reflns 2594 _refine_ls_number_parameters 193 _refine_ls_number_restraints 122 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 1.052 _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 0.02147(3) 0.143562(12) 0.68337(6) 0.07037(18) Uani 1 1 d . . . C1A C 0.1126(2) 0.12838(8) 0.7863(3) 0.0706(8) Uani 0.50 1 d P . 1 N1A N -0.0783(2) 0.12892(8) 0.5953(3) 0.0744(8) Uani 0.50 1 d P . 1 N1B N 0.1126(2) 0.12838(8) 0.7863(3) 0.0706(8) Uani 0.50 1 d P . 2 C1B C -0.0783(2) 0.12892(8) 0.5953(3) 0.0744(8) Uani 0.50 1 d P . 2 N2 N 0.04255(19) 0.20156(7) 0.6558(3) 0.0727(7) Uani 1 1 d . . . C2 C 0.0990(3) 0.22158(11) 0.7197(3) 0.0870(11) Uani 1 1 d . . . H2 H 0.1363 0.2086 0.7700 0.104 Uiso 1 1 calc R . . C3 C 0.1054(3) 0.26052(11) 0.7156(4) 0.0862(10) Uani 1 1 d . . . H3 H 0.1468 0.2728 0.7621 0.103 Uiso 1 1 calc R . . C4 C 0.0524(2) 0.28109(9) 0.6448(3) 0.0729(8) Uani 1 1 d D . . C5 C -0.0054(3) 0.26062(10) 0.5760(4) 0.0786(9) Uani 1 1 d . . . H5 H -0.0424 0.2731 0.5242 0.094 Uiso 1 1 calc R . . C6 C -0.0082(2) 0.22162(10) 0.5838(3) 0.0743(9) Uani 1 1 d . . . H6 H -0.0477 0.2086 0.5362 0.089 Uiso 1 1 calc R . . C7 C 0.0558(4) 0.32450(10) 0.6426(4) 0.1048(15) Uani 1 1 d DU . . C8 C 0.0106(11) 0.3406(3) 0.5440(13) 0.228(9) Uani 0.704(8) 1 d PDU . 1 H8A H -0.0528 0.3373 0.5522 0.342 Uiso 0.704(8) 1 calc PR . 1 H8B H 0.0305 0.3281 0.4754 0.342 Uiso 0.704(8) 1 calc PR . 1 H8C H 0.0241 0.3671 0.5389 0.342 Uiso 0.704(8) 1 calc PR . 1 C9 C 0.0203(11) 0.3385(3) 0.7582(12) 0.221(8) Uani 0.704(8) 1 d PDU . 1 H9A H 0.0494 0.3618 0.7783 0.331 Uiso 0.704(8) 1 calc PR . 1 H9B H 0.0321 0.3198 0.8161 0.331 Uiso 0.704(8) 1 calc PR . 1 H9C H -0.0431 0.3426 0.7527 0.331 Uiso 0.704(8) 1 calc PR . 1 C10 C 0.1555(5) 0.3358(2) 0.6449(9) 0.131(3) Uani 0.704(8) 1 d PDU . 1 H10A H 0.1839 0.3246 0.7106 0.197 Uiso 0.704(8) 1 calc PR . 1 H10B H 0.1605 0.3629 0.6492 0.197 Uiso 0.704(8) 1 calc PR . 1 H10C H 0.1843 0.3270 0.5762 0.197 Uiso 0.704(8) 1 calc PR . 1 C8' C 0.0746(18) 0.3366(7) 0.5171(13) 0.228(9) Uani 0.296(8) 1 d PD . 2 H8D H 0.1338 0.3287 0.4957 0.342 Uiso 0.296(8) 1 calc PR . 2 H8E H 0.0700 0.3636 0.5107 0.342 Uiso 0.296(8) 1 calc PR . 2 H8F H 0.0317 0.3249 0.4670 0.342 Uiso 0.296(8) 1 calc PR . 2 C9' C -0.0447(10) 0.3378(6) 0.657(3) 0.221(8) Uani 0.296(8) 1 d PD . 2 H9D H -0.0460 0.3638 0.6803 0.331 Uiso 0.296(8) 1 calc PR . 2 H9E H -0.0735 0.3225 0.7143 0.331 Uiso 0.296(8) 1 calc PR . 2 H9F H -0.0755 0.3350 0.5852 0.331 Uiso 0.296(8) 1 calc PR . 2 C10' C 0.1085(15) 0.3470(5) 0.7231(17) 0.131(3) Uani 0.296(8) 1 d PD . 2 H10D H 0.1704 0.3400 0.7172 0.197 Uiso 0.296(8) 1 calc PR . 2 H10E H 0.0878 0.3425 0.7999 0.197 Uiso 0.296(8) 1 calc PR . 2 H10F H 0.1020 0.3734 0.7051 0.197 Uiso 0.296(8) 1 calc PR . 2 N3 N 0.0000 0.5000 0.1915(5) 0.0955(13) Uani 1 2 d S . . C11 C -0.0020(3) 0.46852(15) 0.2508(4) 0.0912(12) Uani 1 1 d . . . H11 H -0.0023 0.4457 0.2108 0.109 Uiso 1 1 calc R . . C12 C -0.0036(3) 0.46710(10) 0.3670(4) 0.0810(9) Uani 1 1 d . . . H12 H -0.0072 0.4438 0.4040 0.097 Uiso 1 1 calc R . . C13 C 0.0000 0.5000 0.4310(5) 0.0749(10) Uani 1 2 d SD . . C14 C 0.0000 0.5000 0.5621(6) 0.116(2) Uani 1 2 d SDU . . C15 C -0.005(2) 0.4606(4) 0.6091(18) 0.258(12) Uani 0.50 1 d PDU A -1 H15A H 0.0349 0.4445 0.5664 0.387 Uiso 0.50 1 calc PR A -1 H15B H -0.0648 0.4513 0.6028 0.387 Uiso 0.50 1 calc PR A -1 H15C H 0.0129 0.4608 0.6884 0.387 Uiso 0.50 1 calc PR A -1 C16 C -0.0627(12) 0.5275(6) 0.6110(13) 0.167(6) Uani 0.50 1 d PDU A -1 H16A H -0.0891 0.5421 0.5504 0.251 Uiso 0.50 1 calc PR A -1 H16B H -0.0313 0.5440 0.6625 0.251 Uiso 0.50 1 calc PR A -1 H16C H -0.1088 0.5143 0.6522 0.251 Uiso 0.50 1 calc PR A -1 C17 C 0.0965(8) 0.5151(9) 0.5940(10) 0.204(8) Uani 0.50 1 d PDU A -1 H17A H 0.1409 0.4983 0.5635 0.306 Uiso 0.50 1 calc PR A -1 H17B H 0.1024 0.5164 0.6760 0.306 Uiso 0.50 1 calc PR A -1 H17C H 0.1047 0.5399 0.5619 0.306 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0651(3) 0.0659(2) 0.0801(3) -0.0058(2) -0.0178(2) 0.0041(2) C1A 0.0687(18) 0.0596(15) 0.084(2) -0.0034(13) -0.0185(17) 0.0001(13) N1A 0.0758(19) 0.0568(15) 0.090(2) 0.0000(13) -0.0238(17) 0.0016(14) N1B 0.0687(18) 0.0596(15) 0.084(2) -0.0034(13) -0.0185(17) 0.0001(13) C1B 0.0758(19) 0.0568(15) 0.090(2) 0.0000(13) -0.0238(17) 0.0016(14) N2 0.0638(14) 0.0656(13) 0.089(2) -0.0007(13) -0.0225(12) -0.0011(12) C2 0.092(2) 0.0738(19) 0.096(3) 0.0061(17) -0.042(2) -0.0128(19) C3 0.089(2) 0.077(2) 0.092(3) -0.0079(17) -0.0279(19) -0.0179(19) C4 0.0697(19) 0.0630(16) 0.086(2) -0.0072(14) 0.0071(15) -0.0072(15) C5 0.0716(18) 0.071(2) 0.093(2) 0.0096(17) -0.0152(17) 0.0028(17) C6 0.0627(17) 0.0695(19) 0.091(2) -0.0040(16) -0.0254(16) -0.0039(15) C7 0.123(4) 0.0574(18) 0.133(4) -0.0057(19) 0.021(3) -0.012(2) C8 0.295(18) 0.060(4) 0.330(14) 0.046(6) -0.203(15) 0.001(8) C9 0.329(19) 0.074(4) 0.259(12) -0.064(7) 0.171(14) -0.021(7) C10 0.132(6) 0.075(4) 0.186(9) 0.009(4) -0.008(5) -0.030(4) C8' 0.295(18) 0.060(4) 0.330(14) 0.046(6) -0.203(15) 0.001(8) C9' 0.329(19) 0.074(4) 0.259(12) -0.064(7) 0.171(14) -0.021(7) C10' 0.132(6) 0.075(4) 0.186(9) 0.009(4) -0.008(5) -0.030(4) N3 0.083(3) 0.129(4) 0.074(2) 0.000 0.000 -0.017(2) C11 0.082(2) 0.101(3) 0.090(3) -0.026(2) 0.006(2) -0.010(2) C12 0.082(2) 0.069(2) 0.092(2) 0.0043(18) 0.0032(18) -0.0028(17) C13 0.075(2) 0.080(3) 0.070(2) 0.000 0.000 0.001(2) C14 0.125(5) 0.158(7) 0.065(3) 0.000 0.000 0.029(5) C15 0.42(4) 0.231(15) 0.123(15) 0.099(15) 0.06(2) 0.038(14) C16 0.147(10) 0.265(16) 0.091(9) -0.038(11) 0.038(9) 0.041(13) C17 0.124(8) 0.42(3) 0.067(6) -0.019(13) -0.023(6) 0.014(12) _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 N1A 1.882(3) . ? Cu1 C1A 1.892(3) . ? Cu1 N2 2.097(3) . ? C1A N1A 1.149(4) 3 ? N1A C1A 1.149(4) 11_454 ? N2 C2 1.329(4) . ? N2 C6 1.335(4) . ? C2 C3 1.379(6) . ? C2 H2 0.9300 . ? C3 C4 1.356(5) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 C7 1.534(5) . ? C5 C6 1.380(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.449(9) . ? C7 C10' 1.461(12) . ? C7 C9 1.529(10) . ? C7 C10 1.544(9) . ? C7 C8' 1.548(14) . ? C7 C9' 1.582(14) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C8' H8D 0.9600 . ? C8' H8E 0.9600 . ? C8' H8F 0.9600 . ? C9' H9D 0.9600 . ? C9' H9E 0.9600 . ? C9' H9F 0.9600 . ? C10' H10D 0.9600 . ? C10' H10E 0.9600 . ? C10' H10F 0.9600 . ? N3 C11 1.310(6) . ? N3 C11 1.310(6) 2_565 ? C11 C12 1.354(7) . ? C11 H11 0.9300 . ? C12 C13 1.381(5) . ? C12 H12 0.9300 . ? C13 C12 1.381(5) 2_565 ? C13 C14 1.527(8) . ? C14 C16 1.465(11) 2_565 ? C14 C16 1.465(11) . ? C14 C15 1.497(12) . ? C14 C15 1.497(12) 2_565 ? C14 C17 1.582(12) 2_565 ? C14 C17 1.582(12) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1A Cu1 C1A 146.91(12) . . ? N1A Cu1 N2 107.69(12) . . ? C1A Cu1 N2 105.40(11) . . ? N1A C1A Cu1 175.2(3) 3 . ? C1A N1A Cu1 175.6(3) 11_454 . ? C2 N2 C6 115.5(3) . . ? C2 N2 Cu1 122.0(2) . . ? C6 N2 Cu1 121.9(2) . . ? N2 C2 C3 123.7(3) . . ? N2 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 116.0(3) . . ? C3 C4 C7 121.7(3) . . ? C5 C4 C7 122.3(4) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? N2 C6 C5 123.6(3) . . ? N2 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? C8 C7 C10' 123.2(9) . . ? C8 C7 C9 114.2(7) . . ? C10' C7 C9 56.4(10) . . ? C8 C7 C4 112.9(5) . . ? C10' C7 C4 123.5(8) . . ? C9 C7 C4 107.2(5) . . ? C8 C7 C10 111.3(7) . . ? C10' C7 C10 47.7(9) . . ? C9 C7 C10 103.7(7) . . ? C4 C7 C10 106.9(4) . . ? C8 C7 C8' 39.5(10) . . ? C10' C7 C8' 111.0(10) . . ? C9 C7 C8' 143.7(11) . . ? C4 C7 C8' 107.3(10) . . ? C10 C7 C8' 76.7(10) . . ? C8 C7 C9' 61.7(12) . . ? C10' C7 C9' 106.5(9) . . ? C9 C7 C9' 58.8(11) . . ? C4 C7 C9' 105.2(9) . . ? C10 C7 C9' 147.0(8) . . ? C8' C7 C9' 101.0(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? C7 C8' H8D 109.5 . . ? C7 C8' H8E 109.5 . . ? H8D C8' H8E 109.5 . . ? C7 C8' H8F 109.5 . . ? H8D C8' H8F 109.5 . . ? H8E C8' H8F 109.5 . . ? C7 C9' H9D 109.5 . . ? C7 C9' H9E 109.5 . . ? H9D C9' H9E 109.5 . . ? C7 C9' H9F 109.5 . . ? H9D C9' H9F 109.5 . . ? H9E C9' H9F 109.5 . . ? C7 C10' H10D 109.5 . . ? C7 C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C7 C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C11 N3 C11 116.3(6) . 2_565 ? N3 C11 C12 124.0(5) . . ? N3 C11 H11 118.0 . . ? C12 C11 H11 118.0 . . ? C11 C12 C13 120.5(4) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C12 114.7(5) . 2_565 ? C12 C13 C14 122.7(3) . . ? C12 C13 C14 122.7(3) 2_565 . ? C16 C14 C16 134.2(15) 2_565 . ? C16 C14 C15 43.2(10) 2_565 . ? C16 C14 C15 116.4(9) . . ? C16 C14 C15 116.4(9) 2_565 2_565 ? C16 C14 C15 43.2(10) . 2_565 ? C15 C14 C15 137.0(18) . 2_565 ? C16 C14 C13 112.9(7) 2_565 . ? C16 C14 C13 112.9(7) . . ? C15 C14 C13 111.5(9) . . ? C15 C14 C13 111.5(9) 2_565 . ? C16 C14 C17 105.5(8) 2_565 2_565 ? C16 C14 C17 63.2(9) . 2_565 ? C15 C14 C17 63.7(9) . 2_565 ? C15 C14 C17 105.7(9) 2_565 2_565 ? C13 C14 C17 103.6(5) . 2_565 ? C16 C14 C17 63.2(9) 2_565 . ? C16 C14 C17 105.5(8) . . ? C15 C14 C17 105.7(9) . . ? C15 C14 C17 63.7(9) 2_565 . ? C13 C14 C17 103.6(5) . . ? C17 C14 C17 152.8(10) 2_565 . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1A Cu1 C1A N1A 148(4) . . . 3 ? N2 Cu1 C1A N1A -31(4) . . . 3 ? C1A Cu1 N1A C1A -144(4) . . . 11_454 ? N2 Cu1 N1A C1A 35(4) . . . 11_454 ? N1A Cu1 N2 C2 169.1(3) . . . . ? C1A Cu1 N2 C2 -11.4(4) . . . . ? N1A Cu1 N2 C6 -1.8(3) . . . . ? C1A Cu1 N2 C6 177.7(3) . . . . ? C6 N2 C2 C3 1.1(7) . . . . ? Cu1 N2 C2 C3 -170.3(3) . . . . ? N2 C2 C3 C4 0.6(7) . . . . ? C2 C3 C4 C5 -1.9(6) . . . . ? C2 C3 C4 C7 177.4(4) . . . . ? C3 C4 C5 C6 1.5(6) . . . . ? C7 C4 C5 C6 -177.8(4) . . . . ? C2 N2 C6 C5 -1.4(6) . . . . ? Cu1 N2 C6 C5 170.0(3) . . . . ? C4 C5 C6 N2 0.1(7) . . . . ? C3 C4 C7 C8 166.2(9) . . . . ? C5 C4 C7 C8 -14.5(10) . . . . ? C3 C4 C7 C10' -6.4(13) . . . . ? C5 C4 C7 C10' 172.8(12) . . . . ? C3 C4 C7 C9 -67.1(9) . . . . ? C5 C4 C7 C9 112.1(8) . . . . ? C3 C4 C7 C10 43.6(7) . . . . ? C5 C4 C7 C10 -137.2(6) . . . . ? C3 C4 C7 C8' 124.5(11) . . . . ? C5 C4 C7 C8' -56.3(11) . . . . ? C3 C4 C7 C9' -128.5(12) . . . . ? C5 C4 C7 C9' 50.7(12) . . . . ? C11 N3 C11 C12 1.2(3) 2_565 . . . ? N3 C11 C12 C13 -2.3(6) . . . . ? C11 C12 C13 C12 1.1(3) . . . 2_565 ? C11 C12 C13 C14 -178.9(3) . . . . ? C12 C13 C14 C16 46.7(11) . . . 2_565 ? C12 C13 C14 C16 -133.3(11) 2_565 . . 2_565 ? C12 C13 C14 C16 -133.3(11) . . . . ? C12 C13 C14 C16 46.7(11) 2_565 . . . ? C12 C13 C14 C15 -0.2(16) . . . . ? C12 C13 C14 C15 179.8(16) 2_565 . . . ? C12 C13 C14 C15 179.8(15) . . . 2_565 ? C12 C13 C14 C15 -0.2(15) 2_565 . . 2_565 ? C12 C13 C14 C17 -67.0(12) . . . 2_565 ? C12 C13 C14 C17 113.0(12) 2_565 . . 2_565 ? C12 C13 C14 C17 113.0(12) . . . . ? C12 C13 C14 C17 -67.0(12) 2_565 . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 66.93 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.172 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.053 # Attachment 'RDP_CuCN_Amines_Structures.cif' data_p21onc _database_code_depnum_ccdc_archive 'CCDC 743728' #TrackingRef 'RDP_CuCN_Amines_Structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Cu N2' _chemical_formula_sum 'C7 H7 Cu N2' _chemical_formula_weight 182.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0593(2) _cell_length_b 8.72760(10) _cell_length_c 8.9901(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.7090(10) _cell_angle_gamma 90.00 _cell_volume 747.57(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3937 _cell_measurement_theta_min 4.64 _cell_measurement_theta_max 67.03 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 3.451 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4010 _exptl_absorpt_correction_T_max 0.7603 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 7274 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 66.99 _reflns_number_total 1273 _reflns_number_gt 1134 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0496P)^2^+0.1720P] 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 1273 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.75650(3) 1.12939(3) 0.39095(4) 0.02694(17) Uani 1 1 d . . . N1A N 0.7565(2) 1.2094(2) 0.5892(2) 0.0274(6) Uani 0.65(2) 1 d P . 1 C1A C 0.7547(2) 1.2306(2) 0.2047(3) 0.0290(6) Uani 0.65(2) 1 d P . 1 C1B C 0.7565(2) 1.2094(2) 0.5892(2) 0.0274(6) Uani 0.35(2) 1 d P . 2 N1B N 0.7547(2) 1.2306(2) 0.2047(3) 0.0290(6) Uani 0.35(2) 1 d P . 2 N2 N 0.77186(19) 0.8960(2) 0.4072(2) 0.0234(4) Uani 1 1 d . . . C2 C 0.8734(2) 0.8374(3) 0.5318(3) 0.0274(5) Uani 1 1 d . . . H2 H 0.9298 0.9067 0.6073 0.033 Uiso 1 1 calc R . . C3 C 0.8999(2) 0.6837(3) 0.5555(3) 0.0329(5) Uani 1 1 d . . . H3 H 0.9713 0.6475 0.6459 0.039 Uiso 1 1 calc R . . C4 C 0.8188(3) 0.5820(3) 0.4428(3) 0.0352(6) Uani 1 1 d . . . H4 H 0.8342 0.4747 0.4545 0.042 Uiso 1 1 calc R . . C5 C 0.7165(3) 0.6400(2) 0.3150(3) 0.0313(5) Uani 1 1 d . . . H5 H 0.6613 0.5723 0.2367 0.038 Uiso 1 1 calc R . . C6 C 0.6928(2) 0.7973(2) 0.2990(2) 0.0250(5) Uani 1 1 d . . . C7 C 0.5789(3) 0.8624(3) 0.1635(3) 0.0337(6) Uani 1 1 d . . . H7A H 0.4950 0.8794 0.1941 0.051 Uiso 1 1 calc R . . H7B H 0.5569 0.7907 0.0751 0.051 Uiso 1 1 calc R . . H7C H 0.6101 0.9601 0.1322 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0333(2) 0.0183(2) 0.0280(2) 0.00026(11) 0.00820(16) 0.00166(11) N1A 0.0387(12) 0.0202(11) 0.0214(11) 0.0039(8) 0.0071(8) 0.0030(7) C1A 0.0362(12) 0.0203(10) 0.0283(13) -0.0071(9) 0.0075(8) -0.0012(8) C1B 0.0387(12) 0.0202(11) 0.0214(11) 0.0039(8) 0.0071(8) 0.0030(7) N1B 0.0362(12) 0.0203(10) 0.0283(13) -0.0071(9) 0.0075(8) -0.0012(8) N2 0.0300(10) 0.0199(9) 0.0221(10) -0.0008(7) 0.0108(8) -0.0003(7) C2 0.0326(12) 0.0262(11) 0.0236(11) 0.0010(9) 0.0092(9) -0.0015(9) C3 0.0331(13) 0.0297(12) 0.0364(14) 0.0113(10) 0.0120(10) 0.0036(10) C4 0.0451(15) 0.0204(11) 0.0474(15) 0.0038(10) 0.0248(12) 0.0020(10) C5 0.0380(14) 0.0227(13) 0.0390(15) -0.0062(9) 0.0205(11) -0.0067(9) C6 0.0284(11) 0.0260(12) 0.0236(11) -0.0026(8) 0.0124(9) -0.0032(8) C7 0.0326(13) 0.0384(14) 0.0277(13) -0.0024(9) 0.0061(10) -0.0016(9) _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 C1A 1.888(2) . ? Cu1 N1A 1.914(2) . ? Cu1 N2 2.0444(19) . ? N1A C1A 1.168(3) 4_586 ? C1A N1A 1.168(3) 4_585 ? N2 C2 1.351(3) . ? N2 C6 1.351(3) . ? C2 C3 1.370(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(4) . ? C3 H3 0.9500 . ? C4 C5 1.369(4) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 H5 0.9500 . ? C6 C7 1.491(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 C1A Cu1 N1A 130.71(8) . . ? C1A Cu1 N2 120.58(8) . . ? N1A Cu1 N2 108.61(7) . . ? C1A N1A Cu1 174.69(18) 4_586 . ? N1A C1A Cu1 178.1(2) 4_585 . ? C2 N2 C6 117.99(19) . . ? C2 N2 Cu1 117.16(15) . . ? C6 N2 Cu1 124.76(15) . . ? N2 C2 C3 123.9(2) . . ? N2 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? N2 C6 C5 120.8(2) . . ? N2 C6 C7 117.76(19) . . ? C5 C6 C7 121.4(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A Cu1 N2 C2 127.80(16) . . . . ? N1A Cu1 N2 C2 -48.99(17) . . . . ? C1A Cu1 N2 C6 -48.73(19) . . . . ? N1A Cu1 N2 C6 134.49(17) . . . . ? C6 N2 C2 C3 -0.7(3) . . . . ? Cu1 N2 C2 C3 -177.48(19) . . . . ? N2 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C2 N2 C6 C5 -0.6(3) . . . . ? Cu1 N2 C6 C5 175.91(18) . . . . ? C2 N2 C6 C7 178.8(2) . . . . ? Cu1 N2 C6 C7 -4.7(3) . . . . ? C4 C5 C6 N2 1.4(3) . . . . ? C4 C5 C6 C7 -178.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 66.99 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.537 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.078 # Attachment 'CCDC743729 RDP253(CuCN)2(3EtPy)3.cif' data_p212121 _database_code_depnum_ccdc_archive 'CCDC 743729' #TrackingRef 'CCDC743729 RDP253(CuCN)2(3EtPy)3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H27 Cu2 N5' _chemical_formula_sum 'C23 H27 Cu2 N5' _chemical_formula_weight 500.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6557(2) _cell_length_b 16.5520(4) _cell_length_c 17.2948(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2477.81(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9869 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 67.81 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 2.242 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4958 _exptl_absorpt_correction_T_max 0.7326 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex II CCD' _diffrn_measurement_method '\w and \y' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 26626 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 67.00 _reflns_number_total 4362 _reflns_number_gt 4327 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINTPLUS (Bruker AXS, 2004)' _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'XSHELL (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0309P)^2^+0.9641P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(19) _refine_ls_number_reflns 4362 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 1.18042(3) 0.061575(16) -0.018037(15) 0.01914(8) Uani 1 1 d . . . Cu2 Cu 1.05826(3) 0.074033(16) 0.263842(15) 0.01828(8) Uani 1 1 d . . . C1A C 1.1440(2) 0.06440(11) 0.08858(11) 0.0196(5) Uani 0.85(2) 1 d P A 1 N1A N 1.12319(17) 0.06960(10) 0.15463(9) 0.0191(4) Uani 0.85(2) 1 d P A 1 C16A C 0.7841(6) 0.3289(4) 0.4696(3) 0.0585(17) Uani 0.576(7) 1 d P A 1 H16A H 0.7701 0.3435 0.5240 0.088 Uiso 0.576(7) 1 calc PR A 1 H16B H 0.7493 0.2732 0.4614 0.088 Uiso 0.576(7) 1 calc PR A 1 H16C H 0.7234 0.3655 0.4370 0.088 Uiso 0.576(7) 1 calc PR A 1 C23A C 0.6008(10) -0.0656(5) 0.0427(3) 0.0887(19) Uani 0.561(6) 1 d P A 1 H23A H 0.6983 -0.0844 0.0653 0.133 Uiso 0.561(6) 1 calc PR A 1 H23B H 0.6156 -0.0550 -0.0125 0.133 Uiso 0.561(6) 1 calc PR A 1 H23C H 0.5214 -0.1073 0.0494 0.133 Uiso 0.561(6) 1 calc PR A 1 N1B N 1.1440(2) 0.06440(11) 0.08858(11) 0.0196(5) Uani 0.15(2) 1 d P A 2 C1B C 1.12319(17) 0.06960(10) 0.15463(9) 0.0191(4) Uani 0.15(2) 1 d P A 2 C16B C 1.0678(9) 0.3715(4) 0.4911(4) 0.052(2) Uani 0.424(7) 1 d P A 2 H16D H 1.0969 0.4221 0.4656 0.079 Uiso 0.424(7) 1 calc PR A 2 H16E H 1.1558 0.3342 0.4904 0.079 Uiso 0.424(7) 1 calc PR A 2 H16F H 1.0382 0.3825 0.5448 0.079 Uiso 0.424(7) 1 calc PR A 2 C23B C 0.6375(12) 0.0642(6) 0.0192(4) 0.0887(19) Uani 0.439(6) 1 d P A 2 H23D H 0.7418 0.0437 0.0095 0.133 Uiso 0.439(6) 1 calc PR A 2 H23E H 0.6438 0.1193 0.0397 0.133 Uiso 0.439(6) 1 calc PR A 2 H23F H 0.5786 0.0645 -0.0292 0.133 Uiso 0.439(6) 1 calc PR A 2 C2 C 1.1543(2) 0.02370(11) 0.34943(11) 0.0182(4) Uani 1 1 d . . . N2 N 1.28585(19) 0.00731(10) -0.09870(9) 0.0219(4) Uani 1 1 d . . . N3 N 1.0692(2) 0.15791(10) -0.07333(9) 0.0242(3) Uani 1 1 d . A . N4 N 1.02411(19) 0.19836(9) 0.28125(9) 0.0211(3) Uani 1 1 d . A . N5 N 0.82417(19) 0.03949(9) 0.24902(9) 0.0199(3) Uani 1 1 d . A . C3 C 0.9609(3) 0.20133(13) -0.03642(12) 0.0314(5) Uani 1 1 d . . . H3 H 0.9370 0.1885 0.0157 0.038 Uiso 1 1 calc R A . C4 C 0.8834(3) 0.26398(15) -0.07182(15) 0.0386(6) Uani 1 1 d . A . H4 H 0.8068 0.2934 -0.0443 0.046 Uiso 1 1 calc R . . C5 C 0.9176(3) 0.28369(13) -0.14753(14) 0.0339(5) Uani 1 1 d . . . H5 H 0.8654 0.3270 -0.1724 0.041 Uiso 1 1 calc R A . C6 C 1.0290(2) 0.23958(13) -0.18673(12) 0.0259(4) Uani 1 1 d . A . C7 C 1.1008(2) 0.17716(12) -0.14701(12) 0.0229(4) Uani 1 1 d . . . H7 H 1.1766 0.1463 -0.1735 0.027 Uiso 1 1 calc R A . C8 C 1.0719(3) 0.25732(15) -0.26959(13) 0.0374(5) Uani 1 1 d . . . H8A H 1.1232 0.3107 -0.2721 0.045 Uiso 1 1 calc R A . H8B H 1.1469 0.2162 -0.2876 0.045 Uiso 1 1 calc R . . C9 C 0.9343(4) 0.2574(3) -0.32300(17) 0.0810(13) Uani 1 1 d . A . H9A H 0.8893 0.2031 -0.3249 0.122 Uiso 1 1 calc R . . H9B H 0.9672 0.2734 -0.3750 0.122 Uiso 1 1 calc R . . H9C H 0.8570 0.2957 -0.3039 0.122 Uiso 1 1 calc R . . C10 C 1.0259(2) 0.25165(12) 0.22238(12) 0.0241(4) Uani 1 1 d . . . H10 H 1.0448 0.2324 0.1715 0.029 Uiso 1 1 calc R A . C11 C 1.0012(2) 0.33329(12) 0.23329(13) 0.0293(4) Uani 1 1 d . A . H11 H 1.0035 0.3694 0.1906 0.035 Uiso 1 1 calc R . . C12 C 0.9730(2) 0.36186(12) 0.30705(14) 0.0297(5) Uani 1 1 d . . . H12 H 0.9553 0.4178 0.3155 0.036 Uiso 1 1 calc R A . C13 C 0.9708(3) 0.30832(13) 0.36873(13) 0.0292(5) Uani 1 1 d . A . C14 C 0.9972(2) 0.22688(12) 0.35199(12) 0.0245(4) Uani 1 1 d . . . H14 H 0.9959 0.1895 0.3937 0.029 Uiso 1 1 calc R A . C15 C 0.9379(3) 0.33513(14) 0.45033(14) 0.0402(6) Uani 1 1 d . . . H15A H 0.9994 0.3018 0.4865 0.048 Uiso 1 1 calc R A 1 H15B H 0.9711 0.3920 0.4565 0.048 Uiso 1 1 calc R A 1 C17 C 0.7308(3) 0.02658(13) 0.30901(13) 0.0265(4) Uani 1 1 d . . . H17 H 0.7725 0.0294 0.3597 0.032 Uiso 1 1 calc R A . C18 C 0.5746(3) 0.00919(15) 0.30020(15) 0.0358(5) Uani 1 1 d . A . H18 H 0.5104 0.0013 0.3441 0.043 Uiso 1 1 calc R . . C19 C 0.5147(3) 0.00353(14) 0.22655(15) 0.0371(5) Uani 1 1 d . . . H19 H 0.4082 -0.0083 0.2193 0.044 Uiso 1 1 calc R A . C20 C 0.6095(2) 0.01502(14) 0.16329(14) 0.0308(5) Uani 1 1 d . A . C21 C 0.7630(2) 0.03373(13) 0.17815(12) 0.0250(4) Uani 1 1 d . . . H21 H 0.8290 0.0431 0.1352 0.030 Uiso 1 1 calc R A . C22 C 0.5527(3) 0.00733(19) 0.08086(15) 0.0459(6) Uani 1 1 d . . . H22A H 0.4384 0.0096 0.0809 0.055 Uiso 1 1 calc R A 1 H22B H 0.5908 0.0542 0.0508 0.055 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01964(14) 0.02046(15) 0.01732(13) -0.00101(10) 0.00070(11) -0.00066(11) Cu2 0.01896(14) 0.01601(13) 0.01987(13) -0.00108(10) -0.00130(11) 0.00112(10) C1A 0.0164(9) 0.0159(9) 0.0264(11) 0.0015(7) 0.0015(7) -0.0005(7) N1A 0.0177(8) 0.0183(8) 0.0213(9) 0.0013(7) 0.0008(6) -0.0011(6) C16A 0.053(3) 0.075(4) 0.048(3) -0.032(3) 0.015(2) -0.007(3) C23A 0.123(5) 0.098(4) 0.045(2) -0.017(3) -0.038(3) 0.039(4) N1B 0.0164(9) 0.0159(9) 0.0264(11) 0.0015(7) 0.0015(7) -0.0005(7) C1B 0.0177(8) 0.0183(8) 0.0213(9) 0.0013(7) 0.0008(6) -0.0011(6) C16B 0.075(5) 0.043(4) 0.040(3) -0.013(3) -0.017(3) -0.007(3) C23B 0.123(5) 0.098(4) 0.045(2) -0.017(3) -0.038(3) 0.039(4) C2 0.0177(9) 0.0175(9) 0.0195(9) -0.0025(7) 0.0028(8) -0.0008(7) N2 0.0217(9) 0.0232(8) 0.0209(8) 0.0011(7) -0.0015(7) 0.0019(7) N3 0.0280(9) 0.0218(8) 0.0228(8) -0.0002(7) 0.0018(7) 0.0065(7) N4 0.0242(9) 0.0160(7) 0.0232(8) 0.0006(6) -0.0032(6) 0.0013(6) N5 0.0164(8) 0.0201(7) 0.0232(8) 0.0008(6) 0.0007(6) 0.0017(6) C3 0.0361(13) 0.0301(11) 0.0280(11) -0.0021(9) 0.0059(9) 0.0113(10) C4 0.0427(14) 0.0320(12) 0.0410(13) -0.0022(10) 0.0088(11) 0.0195(10) C5 0.0334(12) 0.0255(11) 0.0429(13) 0.0063(9) 0.0038(10) 0.0117(9) C6 0.0198(11) 0.0241(10) 0.0337(11) 0.0062(9) 0.0026(8) 0.0021(8) C7 0.0208(10) 0.0212(10) 0.0267(10) 0.0017(8) 0.0041(8) 0.0051(7) C8 0.0309(12) 0.0414(13) 0.0399(12) 0.0191(11) 0.0087(11) 0.0124(10) C9 0.055(2) 0.153(4) 0.0349(14) 0.031(2) 0.0006(15) 0.017(2) C10 0.0260(11) 0.0215(10) 0.0246(10) 0.0050(8) -0.0022(8) 0.0012(7) C11 0.0304(11) 0.0203(10) 0.0371(12) 0.0104(9) -0.0026(10) 0.0008(8) C12 0.0285(12) 0.0146(9) 0.0461(13) -0.0006(9) -0.0048(10) 0.0023(8) C13 0.0334(12) 0.0222(10) 0.0321(11) -0.0050(8) -0.0049(9) 0.0018(8) C14 0.0321(11) 0.0174(9) 0.0242(10) -0.0005(8) -0.0045(8) 0.0025(8) C15 0.0571(16) 0.0272(11) 0.0363(12) -0.0129(10) -0.0043(12) 0.0081(11) C17 0.0267(11) 0.0257(10) 0.0273(11) 0.0036(8) 0.0035(9) -0.0022(8) C18 0.0243(11) 0.0375(12) 0.0455(13) 0.0052(10) 0.0127(10) -0.0022(10) C19 0.0162(10) 0.0382(12) 0.0568(15) -0.0036(11) 0.0001(10) 0.0001(9) C20 0.0184(11) 0.0356(12) 0.0384(12) -0.0053(10) -0.0045(9) 0.0052(8) C21 0.0170(10) 0.0309(11) 0.0270(10) -0.0011(8) -0.0002(8) 0.0026(8) C22 0.0225(12) 0.0699(18) 0.0454(14) -0.0077(13) -0.0144(11) 0.0046(12) _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 C1A 1.8713(18) . ? Cu1 N2 1.8936(17) . ? Cu1 N3 2.0936(17) . ? Cu2 C2 1.8911(19) . ? Cu2 N1A 1.9720(16) . ? Cu2 N4 2.1006(16) . ? Cu2 N5 2.1209(16) . ? C1A N1A 1.160(2) . ? C16A C15 1.376(6) . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C23A C22 1.438(7) . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C16B C15 1.458(7) . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C23B C22 1.600(11) . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? C2 N2 1.156(3) 2_755 ? N2 C2 1.156(3) 2_754 ? N3 C7 1.342(3) . ? N3 C3 1.343(3) . ? N4 C14 1.332(3) . ? N4 C10 1.347(3) . ? N5 C17 1.333(3) . ? N5 C21 1.339(3) . ? C3 C4 1.379(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 C7 1.387(3) . ? C6 C8 1.509(3) . ? C7 H7 0.9500 . ? C8 C9 1.507(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.398(3) . ? C13 C15 1.507(3) . ? C14 H14 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C18 H18 0.9500 . ? C19 C20 1.381(3) . ? C19 H19 0.9500 . ? C20 C21 1.388(3) . ? C20 C22 1.513(3) . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 C1A Cu1 N2 144.99(7) . . ? C1A Cu1 N3 110.71(7) . . ? N2 Cu1 N3 104.26(7) . . ? C2 Cu2 N1A 127.45(7) . . ? C2 Cu2 N4 112.41(7) . . ? N1A Cu2 N4 102.35(7) . . ? C2 Cu2 N5 113.32(7) . . ? N1A Cu2 N5 98.42(6) . . ? N4 Cu2 N5 98.45(6) . . ? N1A C1A Cu1 177.07(16) . . ? C1A N1A Cu2 172.10(15) . . ? C15 C16A H16A 109.5 . . ? C15 C16A H16B 109.5 . . ? C15 C16A H16C 109.5 . . ? C22 C23A H23A 109.5 . . ? C22 C23A H23B 109.5 . . ? C22 C23A H23C 109.5 . . ? C15 C16B H16D 109.5 . . ? C15 C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15 C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C22 C23B H23D 109.5 . . ? C22 C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C22 C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? N2 C2 Cu2 179.35(17) 2_755 . ? C2 N2 Cu1 176.56(15) 2_754 . ? C7 N3 C3 117.81(18) . . ? C7 N3 Cu1 121.41(14) . . ? C3 N3 Cu1 120.76(14) . . ? C14 N4 C10 117.66(17) . . ? C14 N4 Cu2 120.23(13) . . ? C10 N4 Cu2 122.10(13) . . ? C17 N5 C21 117.47(17) . . ? C17 N5 Cu2 121.93(13) . . ? C21 N5 Cu2 120.52(13) . . ? N3 C3 C4 122.1(2) . . ? N3 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 117.48(19) . . ? C5 C6 C8 122.21(19) . . ? C7 C6 C8 120.32(19) . . ? N3 C7 C6 123.78(19) . . ? N3 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? C9 C8 C6 112.8(2) . . ? C9 C8 H8A 109.0 . . ? C6 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C6 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 C11 122.38(19) . . ? N4 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C12 119.22(19) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C13 119.58(18) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 117.0(2) . . ? C12 C13 C15 122.33(19) . . ? C14 C13 C15 120.6(2) . . ? N4 C14 C13 124.11(19) . . ? N4 C14 H14 117.9 . . ? C13 C14 H14 117.9 . . ? C16A C15 C16B 131.3(4) . . ? C16A C15 C13 112.8(3) . . ? C16B C15 C13 115.4(4) . . ? C16A C15 H15A 109.0 . . ? C16B C15 H15A 60.6 . . ? C13 C15 H15A 109.0 . . ? C16A C15 H15B 109.0 . . ? C16B C15 H15B 48.1 . . ? C13 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N5 C17 C18 122.5(2) . . ? N5 C17 H17 118.7 . . ? C18 C17 H17 118.7 . . ? C19 C18 C17 118.8(2) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C18 C19 C20 119.9(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 116.9(2) . . ? C19 C20 C22 122.8(2) . . ? C21 C20 C22 120.3(2) . . ? N5 C21 C20 124.3(2) . . ? N5 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? C23A C22 C20 114.1(3) . . ? C23A C22 C23B 93.2(5) . . ? C20 C22 C23B 115.4(4) . . ? C23A C22 H22A 108.7 . . ? C20 C22 H22A 108.7 . . ? C23B C22 H22A 115.9 . . ? C23A C22 H22B 108.7 . . ? C20 C22 H22B 108.7 . . ? C23B C22 H22B 15.6 . . ? H22A C22 H22B 107.6 . . ? 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 N2 Cu1 C1A N1A 127(3) . . . . ? N3 Cu1 C1A N1A -49(3) . . . . ? Cu1 C1A N1A Cu2 120(3) . . . . ? C2 Cu2 N1A C1A 128.4(11) . . . . ? N4 Cu2 N1A C1A -100.3(11) . . . . ? N5 Cu2 N1A C1A 0.3(11) . . . . ? N1A Cu2 C2 N2 5(16) . . . 2_755 ? N4 Cu2 C2 N2 -122(16) . . . 2_755 ? N5 Cu2 C2 N2 127(16) . . . 2_755 ? C1A Cu1 N2 C2 168(3) . . . 2_754 ? N3 Cu1 N2 C2 -15(3) . . . 2_754 ? C1A Cu1 N3 C7 167.71(15) . . . . ? N2 Cu1 N3 C7 -10.41(18) . . . . ? C1A Cu1 N3 C3 -13.88(19) . . . . ? N2 Cu1 N3 C3 168.00(17) . . . . ? C2 Cu2 N4 C14 -31.92(17) . . . . ? N1A Cu2 N4 C14 -171.70(15) . . . . ? N5 Cu2 N4 C14 87.69(16) . . . . ? C2 Cu2 N4 C10 149.17(16) . . . . ? N1A Cu2 N4 C10 9.39(17) . . . . ? N5 Cu2 N4 C10 -91.22(16) . . . . ? C2 Cu2 N5 C17 36.98(17) . . . . ? N1A Cu2 N5 C17 174.13(15) . . . . ? N4 Cu2 N5 C17 -81.95(15) . . . . ? C2 Cu2 N5 C21 -146.31(15) . . . . ? N1A Cu2 N5 C21 -9.15(15) . . . . ? N4 Cu2 N5 C21 94.77(15) . . . . ? C7 N3 C3 C4 -0.1(3) . . . . ? Cu1 N3 C3 C4 -178.59(19) . . . . ? N3 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C4 C5 C6 C8 179.7(2) . . . . ? C3 N3 C7 C6 0.6(3) . . . . ? Cu1 N3 C7 C6 179.05(16) . . . . ? C5 C6 C7 N3 -0.5(3) . . . . ? C8 C6 C7 N3 179.8(2) . . . . ? C5 C6 C8 C9 -54.1(4) . . . . ? C7 C6 C8 C9 125.5(3) . . . . ? C14 N4 C10 C11 0.0(3) . . . . ? Cu2 N4 C10 C11 178.99(16) . . . . ? N4 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -0.3(3) . . . . ? C11 C12 C13 C15 -178.8(2) . . . . ? C10 N4 C14 C13 0.0(3) . . . . ? Cu2 N4 C14 C13 -178.95(17) . . . . ? C12 C13 C14 N4 0.1(3) . . . . ? C15 C13 C14 N4 178.7(2) . . . . ? C12 C13 C15 C16A 92.9(4) . . . . ? C14 C13 C15 C16A -85.5(4) . . . . ? C12 C13 C15 C16B -80.1(4) . . . . ? C14 C13 C15 C16B 101.4(4) . . . . ? C21 N5 C17 C18 -1.2(3) . . . . ? Cu2 N5 C17 C18 175.61(17) . . . . ? N5 C17 C18 C19 1.3(3) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 C21 -1.3(3) . . . . ? C18 C19 C20 C22 178.2(2) . . . . ? C17 N5 C21 C20 -0.2(3) . . . . ? Cu2 N5 C21 C20 -177.07(17) . . . . ? C19 C20 C21 N5 1.5(3) . . . . ? C22 C20 C21 N5 -178.0(2) . . . . ? C19 C20 C22 C23A -105.0(5) . . . . ? C21 C20 C22 C23A 74.5(5) . . . . ? C19 C20 C22 C23B 148.7(4) . . . . ? C21 C20 C22 C23B -31.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.650 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.046