# 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 _publ_contact_author_name 'Andrew Johnson' _publ_contact_author_email A.L.JOHNSON@BATH.AC.UK _publ_section_title ; Unprecedented double migratory insertion of phenyl isocyanide into cyclopentadienyl C-H bonds ; _publ_contact_author_address ; Department of Chemistry University of Bath Bath, BA2 7AY United Kingdom ; _publ_contact_author_fax '+44 (0) 1225 386231' _publ_contact_author_phone '+44 (0) 1225 384467' loop_ _publ_author_name 'Andrew Johnson' 'Andrew J. Kingsley' 'Raj Odedra' 'Paul Raithby' 'Mark R Warren' ; A.M.Willcocks ; # Attachment 'B818701k Cif data.cif' data_k08alj22 _database_code_depnum_ccdc_archive 'CCDC 706302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I),(h5-cyclopentadienyl)(phenyl isocyanide) ; _chemical_name_common 'Copper(i),(h5-cyclopentadienyl)(phenyl isocyanide)' _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cu N' _chemical_formula_sum 'C12 H10 Cu N' _chemical_formula_weight 231.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.5690(1) _cell_length_b 8.0000(2) _cell_length_c 23.7374(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.623(1) _cell_angle_gamma 90.00 _cell_volume 1045.59(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11952 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 2.044 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 0.819 _exptl_absorpt_process_details 'sortav (blessing, 1995)' _exptl_special_details ; multi-scan from symmetry-related measurements sortav (blessing 1995) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'nonius kappa ccd' _diffrn_measurement_method '6046 images with \f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11429 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0581 _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 -30 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2390 _reflns_number_gt 1559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'collect, nonius program suite version 1.9 (1997)' _computing_cell_refinement 'hkl scalepack (otwinowski & minor 1997)' _computing_data_reduction 'denzo and scalepack (otwinowski & minor, 1997)' _computing_structure_solution 'shelxs-97 (sheldrick, 1990)' _computing_structure_refinement 'shelxl-97 (sheldrick, 1997)' _computing_molecular_graphics 'ortep3 for windows - l. j. farrugia, j. appl. crystallogr. 1997, 30, 565' _computing_publication_material 'shelxtl (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^)+(0.0520P)^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 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2390 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.29909(6) 0.26142(4) -0.005046(14) 0.03535(19) Uani 1 1 d . . . N1 N 0.5373(5) 0.2744(2) 0.11470(10) 0.0315(6) Uani 1 1 d . . . C1 C 0.2771(5) 0.1475(3) -0.09019(11) 0.0330(7) Uani 1 1 d . . . H1 H 0.3957 0.0725 -0.1004 0.040 Uiso 1 1 calc R . . C2 C 0.2797(5) 0.3210(4) -0.09602(11) 0.0337(7) Uani 1 1 d . . . H2 H 0.4008 0.3840 -0.1108 0.040 Uiso 1 1 calc R . . C3 C 0.0754(6) 0.3863(4) -0.07663(13) 0.0495(9) Uani 1 1 d . . . H3 H 0.0323 0.5011 -0.0758 0.059 Uiso 1 1 calc R . . C4 C -0.0551(6) 0.2518(6) -0.05866(14) 0.0670(14) Uani 1 1 d . . . H4 H -0.2033 0.2595 -0.0435 0.080 Uiso 1 1 calc R . . C5 C 0.0710(6) 0.1026(5) -0.06685(12) 0.0520(10) Uani 1 1 d . . . H5 H 0.0242 -0.0075 -0.0581 0.062 Uiso 1 1 calc R . . C6 C 0.4495(5) 0.2715(3) 0.06736(13) 0.0313(7) Uani 1 1 d . . . C7 C 0.6297(5) 0.2806(3) 0.17307(11) 0.0288(6) Uani 1 1 d . . . C8 C 0.8479(5) 0.2023(3) 0.19313(12) 0.0346(7) Uani 1 1 d . . . H8 H 0.9377 0.1464 0.1678 0.042 Uiso 1 1 calc R . . C9 C 0.9313(5) 0.2076(4) 0.25081(13) 0.0373(7) Uani 1 1 d . . . H9 H 1.0814 0.1557 0.2652 0.045 Uiso 1 1 calc R . . C10 C 0.8009(6) 0.2868(3) 0.28783(13) 0.0363(7) Uani 1 1 d . . . H10 H 0.8594 0.2877 0.3275 0.044 Uiso 1 1 calc R . . C11 C 0.5842(6) 0.3653(3) 0.26704(12) 0.0411(7) Uani 1 1 d . . . H11 H 0.4947 0.4210 0.2925 0.049 Uiso 1 1 calc R . . C12 C 0.4973(5) 0.3629(3) 0.20908(12) 0.0356(7) Uani 1 1 d . . . H12 H 0.3491 0.4171 0.1945 0.043 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 0.0346(3) 0.0465(3) 0.0221(2) -0.00292(14) -0.00482(16) -0.00181(15) N1 0.0385(13) 0.0281(12) 0.0251(14) -0.0025(9) -0.0042(10) -0.0033(9) C1 0.0435(17) 0.0325(15) 0.0217(14) -0.0048(11) 0.0007(12) -0.0025(12) C2 0.0392(16) 0.0352(15) 0.0249(15) 0.0014(12) -0.0005(12) -0.0007(13) C3 0.046(2) 0.065(2) 0.0325(18) -0.0049(16) -0.0081(15) 0.0240(17) C4 0.0210(15) 0.158(5) 0.0201(17) -0.015(2) -0.0015(13) -0.005(2) C5 0.062(2) 0.071(2) 0.0200(16) 0.0009(15) -0.0046(15) -0.0397(19) C6 0.0316(15) 0.0317(15) 0.0292(16) -0.0019(11) 0.0003(12) -0.0025(11) C7 0.0343(15) 0.0270(13) 0.0224(14) -0.0020(10) -0.0042(12) -0.0062(11) C8 0.0339(15) 0.0383(15) 0.0306(16) -0.0038(12) 0.0017(12) 0.0001(12) C9 0.0324(16) 0.0434(16) 0.0322(17) 0.0027(13) -0.0077(13) -0.0009(13) C10 0.0454(17) 0.0391(15) 0.0213(15) 0.0006(12) -0.0054(13) -0.0069(13) C11 0.0505(18) 0.0422(17) 0.0319(16) -0.0045(13) 0.0107(14) -0.0019(14) C12 0.0361(16) 0.0331(15) 0.0350(17) 0.0015(12) -0.0030(13) 0.0004(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 C6 1.797(3) . ? Cu1 C4 2.183(3) . ? Cu1 C3 2.192(3) . ? Cu1 C5 2.196(3) . ? Cu1 C2 2.198(3) . ? Cu1 C1 2.204(3) . ? N1 C6 1.157(4) . ? N1 C7 1.405(3) . ? C1 C5 1.394(4) . ? C1 C2 1.395(4) . ? C1 H1 0.9500 . ? C2 C3 1.392(4) . ? C2 H2 0.9500 . ? C3 C4 1.401(5) . ? C3 H3 0.9500 . ? C4 C5 1.413(5) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C7 C12 1.378(4) . ? C7 C8 1.386(4) . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(5) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 C12 1.388(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 C6 Cu1 C4 144.10(13) . . ? C6 Cu1 C3 148.24(11) . . ? C4 Cu1 C3 37.35(13) . . ? C6 Cu1 C5 143.59(12) . . ? C4 Cu1 C5 37.65(13) . . ? C3 Cu1 C5 62.69(14) . . ? C6 Cu1 C2 151.26(13) . . ? C4 Cu1 C2 61.84(12) . . ? C3 Cu1 C2 36.97(11) . . ? C5 Cu1 C2 62.03(11) . . ? C6 Cu1 C1 148.15(12) . . ? C4 Cu1 C1 61.93(12) . . ? C3 Cu1 C1 62.00(11) . . ? C5 Cu1 C1 36.95(11) . . ? C2 Cu1 C1 36.97(11) . . ? C6 N1 C7 176.4(3) . . ? C5 C1 C2 108.5(3) . . ? C5 C1 Cu1 71.22(17) . . ? C2 C1 Cu1 71.30(15) . . ? C5 C1 H1 125.8 . . ? C2 C1 H1 125.8 . . ? Cu1 C1 H1 123.4 . . ? C3 C2 C1 108.6(3) . . ? C3 C2 Cu1 71.26(17) . . ? C1 C2 Cu1 71.73(15) . . ? C3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? Cu1 C2 H2 123.0 . . ? C2 C3 C4 107.4(3) . . ? C2 C3 Cu1 71.77(16) . . ? C4 C3 Cu1 70.98(18) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? Cu1 C3 H3 122.7 . . ? C3 C4 C5 108.4(3) . . ? C3 C4 Cu1 71.67(17) . . ? C5 C4 Cu1 71.68(17) . . ? C3 C4 H4 125.8 . . ? C5 C4 H4 125.8 . . ? Cu1 C4 H4 122.5 . . ? C1 C5 C4 107.0(3) . . ? C1 C5 Cu1 71.83(15) . . ? C4 C5 Cu1 70.67(18) . . ? C1 C5 H5 126.5 . . ? C4 C5 H5 126.5 . . ? Cu1 C5 H5 122.7 . . ? N1 C6 Cu1 176.9(3) . . ? C12 C7 C8 121.7(3) . . ? C12 C7 N1 118.5(2) . . ? C8 C7 N1 119.7(3) . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 118.8(3) . . ? C7 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? 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 C6 Cu1 C1 C5 113.4(3) . . . . ? C4 Cu1 C1 C5 -38.4(2) . . . . ? C3 Cu1 C1 C5 -80.9(2) . . . . ? C2 Cu1 C1 C5 -118.0(2) . . . . ? C6 Cu1 C1 C2 -128.6(2) . . . . ? C4 Cu1 C1 C2 79.57(19) . . . . ? C3 Cu1 C1 C2 37.03(17) . . . . ? C5 Cu1 C1 C2 118.0(2) . . . . ? C5 C1 C2 C3 -0.2(3) . . . . ? Cu1 C1 C2 C3 -62.08(19) . . . . ? C5 C1 C2 Cu1 61.86(18) . . . . ? C6 Cu1 C2 C3 -121.2(3) . . . . ? C4 Cu1 C2 C3 38.0(2) . . . . ? C5 Cu1 C2 C3 80.9(2) . . . . ? C1 Cu1 C2 C3 117.8(2) . . . . ? C6 Cu1 C2 C1 121.0(2) . . . . ? C4 Cu1 C2 C1 -79.86(19) . . . . ? C3 Cu1 C2 C1 -117.8(2) . . . . ? C5 Cu1 C2 C1 -36.96(17) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? Cu1 C2 C3 C4 -62.4(2) . . . . ? C1 C2 C3 Cu1 62.38(17) . . . . ? C6 Cu1 C3 C2 128.6(3) . . . . ? C4 Cu1 C3 C2 -116.6(3) . . . . ? C5 Cu1 C3 C2 -78.9(2) . . . . ? C1 Cu1 C3 C2 -37.03(17) . . . . ? C6 Cu1 C3 C4 -114.8(3) . . . . ? C5 Cu1 C3 C4 37.6(2) . . . . ? C2 Cu1 C3 C4 116.6(3) . . . . ? C1 Cu1 C3 C4 79.5(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? Cu1 C3 C4 C5 -62.7(2) . . . . ? C2 C3 C4 Cu1 62.94(19) . . . . ? C6 Cu1 C4 C3 125.4(2) . . . . ? C5 Cu1 C4 C3 -117.4(3) . . . . ? C2 Cu1 C4 C3 -37.60(19) . . . . ? C1 Cu1 C4 C3 -79.7(2) . . . . ? C6 Cu1 C4 C5 -117.2(2) . . . . ? C3 Cu1 C4 C5 117.4(3) . . . . ? C2 Cu1 C4 C5 79.8(2) . . . . ? C1 Cu1 C4 C5 37.67(18) . . . . ? C2 C1 C5 C4 0.4(3) . . . . ? Cu1 C1 C5 C4 62.3(2) . . . . ? C2 C1 C5 Cu1 -61.91(17) . . . . ? C3 C4 C5 C1 -0.4(3) . . . . ? Cu1 C4 C5 C1 -63.06(19) . . . . ? C3 C4 C5 Cu1 62.7(2) . . . . ? C6 Cu1 C5 C1 -125.3(2) . . . . ? C4 Cu1 C5 C1 116.2(3) . . . . ? C3 Cu1 C5 C1 78.9(2) . . . . ? C2 Cu1 C5 C1 36.97(17) . . . . ? C6 Cu1 C5 C4 118.5(3) . . . . ? C3 Cu1 C5 C4 -37.3(2) . . . . ? C2 Cu1 C5 C4 -79.2(2) . . . . ? C1 Cu1 C5 C4 -116.2(3) . . . . ? C12 C7 C8 C9 0.3(4) . . . . ? N1 C7 C8 C9 -178.7(2) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C8 C7 C12 C11 -0.8(4) . . . . ? N1 C7 C12 C11 178.1(2) . . . . ? C10 C11 C12 C7 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.962 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.087 ####END data_k08alj08 _database_code_depnum_ccdc_archive 'CCDC 706303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Copper(I),(n'n-diphenyl-6-aminofulvene-2-aldimine)(phenyl isocyanide) ; _chemical_name_common ;Copper(i),(n'n-diphenyl-6-aminofulvene-2-aldimine)(phenyl isocyanide) ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 Cu N3' _chemical_formula_sum 'C26 H20 Cu N3' _chemical_formula_weight 437.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1900(4) _cell_length_b 10.1970(5) _cell_length_c 10.3120(5) _cell_angle_alpha 80.536(2) _cell_angle_beta 80.213(2) _cell_angle_gamma 83.978(3) _cell_volume 1038.26(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10653 _cell_measurement_theta_min 2.716 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 1.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Copper(I),(n'n-diphenyl-6-aminofulvene-2-aldimine)(phenyl isocyanide) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'nonius kappa ccd' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11479 _diffrn_reflns_av_R_equivalents 0.0734 _diffrn_reflns_av_sigmaI/netI 0.0879 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 7.86 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4604 _reflns_number_gt 3410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'collect, nonius program suite version 1.9 (1997)' _computing_cell_refinement 'hkl scalepack (otwinowski & minor 1997)' _computing_data_reduction 'denzo and scalepack (otwinowski & minor, 1997)' _computing_structure_solution 'shelxs-97 (sheldrick, 1990)' _computing_structure_refinement 'shelxl-97 (sheldrick, 1997)' _computing_molecular_graphics 'ortep3 for windows - l. j. farrugia, j. appl. crystallogr. 1997, 30, 565' _computing_publication_material 'shelxtl (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^)+(0.0255P)^2^+0.2768P] 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 4604 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.45077(3) 0.21044(3) 0.57507(3) 0.02936(12) Uani 1 1 d . . . N1 N 0.5503(2) 0.3604(2) 0.7628(2) 0.0316(5) Uani 1 1 d . . . N3 N 0.2733(2) 0.1498(2) 0.5793(2) 0.0268(5) Uani 1 1 d . . . N2 N 0.5691(2) 0.2035(2) 0.4027(2) 0.0271(5) Uani 1 1 d . . . C1 C 0.5062(3) 0.2989(3) 0.6964(3) 0.0344(6) Uani 1 1 d . . . C2 C 0.6130(2) 0.4305(3) 0.8376(2) 0.0280(5) Uani 1 1 d . . . C3 C 0.6564(3) 0.5547(3) 0.7825(3) 0.0323(6) Uani 1 1 d . . . H3 H 0.6442 0.5928 0.6945 0.039 Uiso 1 1 calc R . . C4 C 0.7180(3) 0.6223(3) 0.8587(3) 0.0367(6) Uani 1 1 d . . . H4 H 0.7465 0.7085 0.8236 0.044 Uiso 1 1 calc R . . C5 C 0.7381(3) 0.5644(3) 0.9857(3) 0.0379(7) Uani 1 1 d . . . H5 H 0.7834 0.6098 1.0361 0.045 Uiso 1 1 calc R . . C6 C 0.6929(3) 0.4412(3) 1.0396(3) 0.0359(6) Uani 1 1 d . . . H6 H 0.7057 0.4030 1.1275 0.043 Uiso 1 1 calc R . . C7 C 0.6292(3) 0.3732(3) 0.9664(3) 0.0316(6) Uani 1 1 d . . . H7 H 0.5969 0.2888 1.0034 0.038 Uiso 1 1 calc R . . C8 C 0.5496(2) 0.1431(3) 0.3062(2) 0.0266(5) Uani 1 1 d . . . H8 H 0.6228 0.1405 0.2358 0.032 Uiso 1 1 calc R . . C9 C 0.4370(2) 0.0807(3) 0.2893(2) 0.0266(5) Uani 1 1 d . . . C10 C 0.4398(3) 0.0295(3) 0.1696(3) 0.0317(6) Uani 1 1 d . . . H10 H 0.5143 0.0284 0.1005 0.038 Uiso 1 1 calc R . . C11 C 0.3176(3) -0.0191(3) 0.1676(3) 0.0329(6) Uani 1 1 d . . . H11 H 0.2946 -0.0588 0.0982 0.040 Uiso 1 1 calc R . . C12 C 0.2354(3) 0.0011(3) 0.2857(3) 0.0303(6) Uani 1 1 d . . . H12 H 0.1460 -0.0229 0.3101 0.036 Uiso 1 1 calc R . . C13 C 0.3042(3) 0.0629(3) 0.3647(2) 0.0274(5) Uani 1 1 d . . . C14 C 0.2340(3) 0.0959(3) 0.4867(2) 0.0277(5) Uani 1 1 d . . . H14 H 0.1432 0.0756 0.5049 0.033 Uiso 1 1 calc R . . C15 C 0.1720(2) 0.1731(3) 0.6891(2) 0.0273(5) Uani 1 1 d . . . C16 C 0.0441(3) 0.2291(3) 0.6721(3) 0.0330(6) Uani 1 1 d . . . H16 H 0.0221 0.2530 0.5850 0.040 Uiso 1 1 calc R . . C17 C -0.0510(3) 0.2500(3) 0.7808(3) 0.0374(6) Uani 1 1 d . . . H17 H -0.1372 0.2894 0.7674 0.045 Uiso 1 1 calc R . . C18 C -0.0223(3) 0.2143(3) 0.9087(3) 0.0396(7) Uani 1 1 d . . . H18 H -0.0885 0.2273 0.9832 0.047 Uiso 1 1 calc R . . C19 C 0.1052(3) 0.1590(3) 0.9265(3) 0.0381(6) Uani 1 1 d . . . H19 H 0.1260 0.1338 1.0140 0.046 Uiso 1 1 calc R . . C20 C 0.2019(3) 0.1402(3) 0.8185(3) 0.0323(6) Uani 1 1 d . . . H20 H 0.2893 0.1047 0.8321 0.039 Uiso 1 1 calc R . . C21 C 0.6936(2) 0.2644(3) 0.3814(2) 0.0270(5) Uani 1 1 d . . . C22 C 0.8141(3) 0.2031(3) 0.3263(2) 0.0301(6) Uani 1 1 d . . . H22 H 0.8170 0.1155 0.3051 0.036 Uiso 1 1 calc R . . C23 C 0.9298(3) 0.2695(3) 0.3022(3) 0.0366(6) Uani 1 1 d . . . H23 H 1.0112 0.2276 0.2631 0.044 Uiso 1 1 calc R . . C24 C 0.9279(3) 0.3962(3) 0.3344(3) 0.0414(7) Uani 1 1 d . . . H24 H 1.0075 0.4413 0.3179 0.050 Uiso 1 1 calc R . . C25 C 0.8089(3) 0.4564(3) 0.3908(3) 0.0394(7) Uani 1 1 d . . . H25 H 0.8066 0.5434 0.4133 0.047 Uiso 1 1 calc R . . C26 C 0.6923(3) 0.3907(3) 0.4149(3) 0.0332(6) Uani 1 1 d . . . H26 H 0.6112 0.4327 0.4546 0.040 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 0.02688(18) 0.0328(2) 0.03096(18) -0.00886(13) -0.00478(12) -0.00708(13) N1 0.0316(12) 0.0333(13) 0.0317(11) -0.0089(10) -0.0067(9) -0.0018(10) N3 0.0265(10) 0.0257(11) 0.0280(11) -0.0033(9) -0.0045(8) -0.0019(9) N2 0.0255(11) 0.0264(11) 0.0309(11) -0.0048(9) -0.0068(9) -0.0035(9) C1 0.0337(14) 0.0358(16) 0.0332(14) -0.0057(12) -0.0026(11) -0.0032(12) C2 0.0277(13) 0.0259(14) 0.0325(13) -0.0098(11) -0.0061(10) -0.0007(10) C3 0.0307(14) 0.0342(15) 0.0307(13) -0.0030(11) -0.0038(11) -0.0010(11) C4 0.0318(14) 0.0312(15) 0.0471(16) -0.0042(12) -0.0048(12) -0.0071(12) C5 0.0351(15) 0.0375(17) 0.0465(16) -0.0142(13) -0.0136(13) -0.0033(12) C6 0.0400(15) 0.0386(16) 0.0318(14) -0.0087(12) -0.0112(12) -0.0015(12) C7 0.0358(15) 0.0255(14) 0.0329(14) -0.0048(11) -0.0029(11) -0.0020(11) C8 0.0248(12) 0.0252(13) 0.0286(13) -0.0026(10) -0.0036(10) -0.0001(10) C9 0.0260(12) 0.0265(14) 0.0281(13) -0.0065(10) -0.0060(10) 0.0011(10) C10 0.0323(14) 0.0326(15) 0.0311(13) -0.0091(11) -0.0045(11) 0.0001(11) C11 0.0359(14) 0.0312(15) 0.0367(14) -0.0118(12) -0.0138(12) -0.0016(12) C12 0.0291(13) 0.0296(14) 0.0348(14) -0.0078(11) -0.0080(11) -0.0051(11) C13 0.0298(13) 0.0251(13) 0.0293(13) -0.0039(10) -0.0090(10) -0.0040(10) C14 0.0280(13) 0.0244(13) 0.0319(13) -0.0020(10) -0.0077(10) -0.0057(10) C15 0.0259(12) 0.0242(13) 0.0331(13) -0.0081(10) -0.0009(10) -0.0086(10) C16 0.0274(13) 0.0329(15) 0.0407(15) -0.0071(12) -0.0077(11) -0.0053(11) C17 0.0245(13) 0.0343(16) 0.0533(18) -0.0102(13) -0.0030(12) -0.0007(11) C18 0.0328(15) 0.0407(17) 0.0444(16) -0.0147(13) 0.0056(12) -0.0051(12) C19 0.0404(16) 0.0397(17) 0.0344(14) -0.0092(12) -0.0038(12) -0.0019(13) C20 0.0297(13) 0.0325(15) 0.0357(14) -0.0095(12) -0.0059(11) 0.0012(11) C21 0.0263(12) 0.0281(14) 0.0275(12) -0.0009(10) -0.0067(10) -0.0069(10) C22 0.0291(13) 0.0271(14) 0.0340(14) -0.0019(11) -0.0065(11) -0.0032(11) C23 0.0252(13) 0.0400(17) 0.0427(15) -0.0022(13) -0.0037(11) -0.0028(12) C24 0.0340(15) 0.0414(18) 0.0505(17) -0.0055(14) -0.0054(13) -0.0157(13) C25 0.0413(16) 0.0296(15) 0.0491(17) -0.0082(13) -0.0051(13) -0.0110(12) C26 0.0323(14) 0.0298(15) 0.0370(14) -0.0056(11) -0.0021(11) -0.0046(11) _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 1.849(3) . ? Cu1 N3 1.964(2) . ? Cu1 N2 1.978(2) . ? N1 C1 1.170(3) . ? N1 C2 1.399(3) . ? N3 C14 1.312(3) . ? N3 C15 1.430(3) . ? N2 C8 1.306(3) . ? N2 C21 1.439(3) . ? C2 C3 1.385(4) . ? C2 C7 1.390(4) . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.380(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.417(4) . ? C8 H8 0.9500 . ? C9 C10 1.412(4) . ? C9 C13 1.455(4) . ? C10 C11 1.393(4) . ? C10 H10 0.9500 . ? C11 C12 1.388(4) . ? C11 H11 0.9500 . ? C12 C13 1.416(4) . ? C12 H12 0.9500 . ? C13 C14 1.411(4) . ? C14 H14 0.9500 . ? C15 C16 1.394(3) . ? C15 C20 1.397(4) . ? C16 C17 1.380(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(4) . ? C17 H17 0.9500 . ? C18 C19 1.390(4) . ? C18 H18 0.9500 . ? C19 C20 1.381(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.385(4) . ? C21 C22 1.392(4) . ? C22 C23 1.387(4) . ? C22 H22 0.9500 . ? C23 C24 1.383(4) . ? C23 H23 0.9500 . ? C24 C25 1.381(4) . ? C24 H24 0.9500 . ? C25 C26 1.391(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 N3 128.01(10) . . ? C1 Cu1 N2 117.50(11) . . ? N3 Cu1 N2 113.41(8) . . ? C1 N1 C2 175.6(3) . . ? C14 N3 C15 115.2(2) . . ? C14 N3 Cu1 126.61(17) . . ? C15 N3 Cu1 118.04(16) . . ? C8 N2 C21 115.1(2) . . ? C8 N2 Cu1 126.72(18) . . ? C21 N2 Cu1 118.08(16) . . ? N1 C1 Cu1 173.3(2) . . ? C3 C2 C7 121.7(2) . . ? C3 C2 N1 119.6(2) . . ? C7 C2 N1 118.7(2) . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 118.8(3) . . ? C6 C7 H7 120.6 . . ? C2 C7 H7 120.6 . . ? N2 C8 C9 130.5(2) . . ? N2 C8 H8 114.7 . . ? C9 C8 H8 114.7 . . ? C10 C9 C8 118.6(2) . . ? C10 C9 C13 106.2(2) . . ? C8 C9 C13 135.0(2) . . ? C11 C10 C9 110.2(2) . . ? C11 C10 H10 124.9 . . ? C9 C10 H10 124.9 . . ? C12 C11 C10 107.4(2) . . ? C12 C11 H11 126.3 . . ? C10 C11 H11 126.3 . . ? C11 C12 C13 110.2(2) . . ? C11 C12 H12 124.9 . . ? C13 C12 H12 124.9 . . ? C14 C13 C12 118.0(2) . . ? C14 C13 C9 135.8(2) . . ? C12 C13 C9 106.1(2) . . ? N3 C14 C13 130.8(2) . . ? N3 C14 H14 114.6 . . ? C13 C14 H14 114.6 . . ? C16 C15 C20 118.4(2) . . ? C16 C15 N3 122.3(2) . . ? C20 C15 N3 119.2(2) . . ? C17 C16 C15 120.6(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.9(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C19 118.9(3) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 120.7(3) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C15 120.4(2) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C26 C21 C22 119.0(2) . . ? C26 C21 N2 118.1(2) . . ? C22 C21 N2 122.9(2) . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C24 C23 C22 120.7(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.5(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 120.5(3) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? 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 C1 Cu1 N3 C14 174.6(2) . . . . ? N2 Cu1 N3 C14 6.9(2) . . . . ? C1 Cu1 N3 C15 -1.1(2) . . . . ? N2 Cu1 N3 C15 -168.80(16) . . . . ? C1 Cu1 N2 C8 177.95(19) . . . . ? N3 Cu1 N2 C8 -12.9(2) . . . . ? C1 Cu1 N2 C21 1.6(2) . . . . ? N3 Cu1 N2 C21 170.69(16) . . . . ? C7 C2 C3 C4 0.3(4) . . . . ? N1 C2 C3 C4 179.9(2) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C3 C4 C5 C6 -2.3(4) . . . . ? C4 C5 C6 C7 1.2(4) . . . . ? C5 C6 C7 C2 0.7(4) . . . . ? C3 C2 C7 C6 -1.5(4) . . . . ? N1 C2 C7 C6 178.9(2) . . . . ? C21 N2 C8 C9 -175.5(2) . . . . ? Cu1 N2 C8 C9 8.0(4) . . . . ? N2 C8 C9 C10 176.0(2) . . . . ? N2 C8 C9 C13 2.3(5) . . . . ? C8 C9 C10 C11 -175.8(2) . . . . ? C13 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 177.6(2) . . . . ? C11 C12 C13 C9 -0.2(3) . . . . ? C10 C9 C13 C14 -176.9(3) . . . . ? C8 C9 C13 C14 -2.6(5) . . . . ? C10 C9 C13 C12 0.4(3) . . . . ? C8 C9 C13 C12 174.7(3) . . . . ? C15 N3 C14 C13 177.9(2) . . . . ? Cu1 N3 C14 C13 2.1(4) . . . . ? C12 C13 C14 N3 178.2(2) . . . . ? C9 C13 C14 N3 -4.8(5) . . . . ? C14 N3 C15 C16 -44.7(3) . . . . ? Cu1 N3 C15 C16 131.5(2) . . . . ? C14 N3 C15 C20 135.9(3) . . . . ? Cu1 N3 C15 C20 -47.9(3) . . . . ? C20 C15 C16 C17 -0.7(4) . . . . ? N3 C15 C16 C17 179.9(3) . . . . ? C15 C16 C17 C18 -0.9(4) . . . . ? C16 C17 C18 C19 1.2(5) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C15 -1.8(4) . . . . ? C16 C15 C20 C19 2.0(4) . . . . ? N3 C15 C20 C19 -178.6(2) . . . . ? C8 N2 C21 C26 136.9(2) . . . . ? Cu1 N2 C21 C26 -46.3(3) . . . . ? C8 N2 C21 C22 -41.8(3) . . . . ? Cu1 N2 C21 C22 135.0(2) . . . . ? C26 C21 C22 C23 -1.8(4) . . . . ? N2 C21 C22 C23 176.9(2) . . . . ? C21 C22 C23 C24 1.1(4) . . . . ? C22 C23 C24 C25 -0.2(4) . . . . ? C23 C24 C25 C26 -0.1(4) . . . . ? C22 C21 C26 C25 1.6(4) . . . . ? N2 C21 C26 C25 -177.1(2) . . . . ? C24 C25 C26 C21 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.326 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.064 ####END data_k08alj06 _database_code_depnum_ccdc_archive 'CCDC 706304' _audit_creation_method shelxl-97 _chemical_name_systematic ; Copper(I),(n'n-diphenyl-6-aminofulvene-2-aldimine)bis(phenyl isocyanide) ; _chemical_name_common ;Copper(i),(n'n-diphenyl-6-aminofulvene-2-aldimine)bis(phenyl isocyanide) ; _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cu N4' _chemical_formula_sum 'C33 H25 Cu N4' _chemical_formula_weight 541.11 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_h-m P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9170(3) _cell_length_b 10.8650(4) _cell_length_c 14.5300(6) _cell_angle_alpha 106.474(1) _cell_angle_beta 97.129(2) _cell_angle_gamma 112.271(2) _cell_volume 1341.18(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23329 _cell_measurement_theta_min 3.84 _cell_measurement_theta_max 29.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.843 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_t_min 0.916 _exptl_absorpt_correction_t_max 0.98 _exptl_absorpt_process_details 'sortav (blessing, 1995)' _exptl_special_details ; multi-scan from symmetry-related measurements sortav (blessing 1995) ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'nonius kappa ccd' _diffrn_measurement_method '6046 images with \f and \w scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14539 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6046 _reflns_number_gt 4863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'collect, nonius program suite version 1.9 (1997)' _computing_cell_refinement 'hkl scalepack (otwinowski & minor 1997)' _computing_data_reduction 'denzo and scalepack (otwinowski & minor, 1997)' _computing_structure_solution 'shelxs-97 (sheldrick, 1990)' _computing_structure_refinement 'shelxl-97 (sheldrick, 1997)' _computing_molecular_graphics 'ortep3 for windows - l. j. farrugia, j. appl. crystallogr. 1997, 30, 565' _computing_publication_material 'shelxtl (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^)+(0.0114P)^2^+0.8305P] 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 6046 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.79154(3) 0.95326(3) 0.28028(2) 0.02705(9) Uani 1 1 d . . . N1 N 0.7781(2) 1.1810(2) 0.45596(15) 0.0325(4) Uani 1 1 d . . . N2 N 0.91435(19) 0.85428(17) 0.32023(13) 0.0255(4) Uani 1 1 d . . . N3 N 0.90018(18) 1.05548(17) 0.19337(13) 0.0246(4) Uani 1 1 d . . . N4 N 0.4982(2) 0.68384(19) 0.16172(15) 0.0329(4) Uani 1 1 d . . . C1 C 0.7870(2) 1.0930(2) 0.39262(18) 0.0323(5) Uani 1 1 d . . . C2 C 0.7724(3) 1.2891(2) 0.53364(17) 0.0294(5) Uani 1 1 d . . . C3 C 0.9046(3) 1.4128(2) 0.5838(2) 0.0387(5) Uani 1 1 d . . . H3 H 0.9963 1.4247 0.5657 0.046 Uiso 1 1 calc R . . C4 C 0.8985(3) 1.5183(3) 0.6612(2) 0.0506(7) Uani 1 1 d . . . H4 H 0.9871 1.6041 0.6968 0.061 Uiso 1 1 calc R . . C5 C 0.7649(4) 1.4998(3) 0.6867(2) 0.0504(7) Uani 1 1 d . . . H5 H 0.7625 1.5730 0.7400 0.061 Uiso 1 1 calc R . . C6 C 0.6345(3) 1.3765(3) 0.6358(2) 0.0408(6) Uani 1 1 d . . . H6 H 0.5430 1.3650 0.6541 0.049 Uiso 1 1 calc R . . C7 C 0.6372(3) 1.2694(2) 0.55803(18) 0.0330(5) Uani 1 1 d . . . H7 H 0.5481 1.1841 0.5222 0.040 Uiso 1 1 calc R . . C8 C 1.0510(2) 0.8740(2) 0.31847(16) 0.0273(4) Uani 1 1 d . . . H8 H 1.0825 0.8106 0.3379 0.033 Uiso 1 1 calc R . . C9 C 1.1608(2) 0.9775(2) 0.29147(16) 0.0267(4) Uani 1 1 d . . . C10 C 1.3132(2) 1.0010(2) 0.31753(18) 0.0335(5) Uani 1 1 d . . . H10 H 1.3484 0.9483 0.3479 0.040 Uiso 1 1 calc R . . C11 C 1.4037(2) 1.1130(3) 0.29196(18) 0.0351(5) Uani 1 1 d . . . H11 H 1.5103 1.1512 0.3035 0.042 Uiso 1 1 calc R . . C12 C 1.3105(2) 1.1588(2) 0.24671(17) 0.0295(5) Uani 1 1 d . . . H12 H 1.3434 1.2330 0.2207 0.035 Uiso 1 1 calc R . . C13 C 1.1584(2) 1.0784(2) 0.24504(16) 0.0245(4) Uani 1 1 d . . . C14 C 1.0441(2) 1.1042(2) 0.19719(15) 0.0238(4) Uani 1 1 d . . . H14 H 1.0772 1.1671 0.1622 0.029 Uiso 1 1 calc R . . C15 C 0.8145(2) 1.0937(2) 0.12967(16) 0.0249(4) Uani 1 1 d . . . C16 C 0.8271(2) 1.0807(2) 0.03378(17) 0.0292(5) Uani 1 1 d . . . H16 H 0.8955 1.0462 0.0094 0.035 Uiso 1 1 calc R . . C17 C 0.7417(3) 1.1169(2) -0.02746(18) 0.0337(5) Uani 1 1 d . . . H17 H 0.7525 1.1084 -0.0927 0.040 Uiso 1 1 calc R . . C18 C 0.6405(3) 1.1655(2) 0.00746(18) 0.0365(5) Uani 1 1 d . . . H18 H 0.5815 1.1905 -0.0339 0.044 Uiso 1 1 calc R . . C19 C 0.6255(3) 1.1776(3) 0.10222(19) 0.0399(6) Uani 1 1 d . . . H19 H 0.5558 1.2107 0.1258 0.048 Uiso 1 1 calc R . . C20 C 0.7111(2) 1.1419(2) 0.16342(18) 0.0348(5) Uani 1 1 d . . . H20 H 0.6995 1.1502 0.2285 0.042 Uiso 1 1 calc R . . C21 C 0.8336(2) 0.7453(2) 0.35668(17) 0.0266(4) Uani 1 1 d . . . C22 C 0.7729(2) 0.6020(2) 0.29716(18) 0.0322(5) Uani 1 1 d . . . H22 H 0.7856 0.5742 0.2319 0.039 Uiso 1 1 calc R . . C23 C 0.6932(3) 0.4996(2) 0.3346(2) 0.0365(5) Uani 1 1 d . . . H23 H 0.6507 0.4015 0.2941 0.044 Uiso 1 1 calc R . . C24 C 0.6749(3) 0.5379(3) 0.4290(2) 0.0374(5) Uani 1 1 d . . . H24 H 0.6207 0.4668 0.4536 0.045 Uiso 1 1 calc R . . C25 C 0.7357(3) 0.6805(3) 0.4883(2) 0.0400(6) Uani 1 1 d . . . H25 H 0.7240 0.7075 0.5539 0.048 Uiso 1 1 calc R . . C26 C 0.8139(3) 0.7842(2) 0.45185(18) 0.0355(5) Uani 1 1 d . . . H26 H 0.8541 0.8821 0.4922 0.043 Uiso 1 1 calc R . . C31 C 0.6032(2) 0.7921(2) 0.20523(18) 0.0306(5) Uani 1 1 d . . . C32 C 0.3816(2) 0.5487(2) 0.10279(18) 0.0320(5) Uani 1 1 d . . . C33 C 0.4141(3) 0.4327(2) 0.07928(19) 0.0370(5) Uani 1 1 d . . . H33 H 0.5119 0.4428 0.1056 0.044 Uiso 1 1 calc R . . C34 C 0.3015(3) 0.3010(2) 0.0165(2) 0.0401(6) Uani 1 1 d . . . H34 H 0.3221 0.2200 0.0000 0.048 Uiso 1 1 calc R . . C35 C 0.1615(3) 0.2869(3) -0.0219(2) 0.0485(7) Uani 1 1 d . . . H35 H 0.0858 0.1970 -0.0666 0.058 Uiso 1 1 calc R . . C36 C 0.1303(3) 0.4031(3) 0.0043(3) 0.0802(13) Uani 1 1 d . . . H36 H 0.0319 0.3924 -0.0212 0.096 Uiso 1 1 calc R . . C37 C 0.2406(3) 0.5357(3) 0.0677(3) 0.0655(10) Uani 1 1 d . . . H37 H 0.2186 0.6157 0.0864 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02257(14) 0.02706(14) 0.03254(16) 0.01181(11) 0.00938(10) 0.01040(10) N1 0.0357(10) 0.0367(10) 0.0322(11) 0.0138(8) 0.0103(8) 0.0214(9) N2 0.0241(9) 0.0241(8) 0.0268(9) 0.0105(7) 0.0072(7) 0.0078(7) N3 0.0214(8) 0.0239(8) 0.0289(9) 0.0096(7) 0.0063(7) 0.0103(7) N4 0.0241(9) 0.0317(9) 0.0414(12) 0.0160(8) 0.0078(8) 0.0087(8) C1 0.0300(11) 0.0368(12) 0.0351(13) 0.0170(10) 0.0093(9) 0.0165(10) C2 0.0343(11) 0.0319(11) 0.0287(11) 0.0130(9) 0.0080(9) 0.0197(9) C3 0.0355(13) 0.0363(12) 0.0452(15) 0.0160(11) 0.0095(11) 0.0158(10) C4 0.0519(16) 0.0325(13) 0.0524(17) 0.0069(12) 0.0082(13) 0.0109(12) C5 0.0673(19) 0.0366(13) 0.0477(16) 0.0070(12) 0.0203(14) 0.0271(13) C6 0.0494(15) 0.0476(14) 0.0432(15) 0.0221(12) 0.0230(12) 0.0317(12) C7 0.0342(12) 0.0347(11) 0.0359(13) 0.0165(10) 0.0094(10) 0.0180(10) C8 0.0259(10) 0.0282(10) 0.0305(12) 0.0134(9) 0.0066(8) 0.0127(9) C9 0.0229(10) 0.0296(10) 0.0281(11) 0.0114(9) 0.0074(8) 0.0112(8) C10 0.0260(11) 0.0441(12) 0.0372(13) 0.0209(10) 0.0083(9) 0.0174(10) C11 0.0188(10) 0.0468(13) 0.0393(13) 0.0191(11) 0.0079(9) 0.0111(9) C12 0.0224(10) 0.0319(11) 0.0350(12) 0.0147(9) 0.0100(9) 0.0098(9) C13 0.0205(9) 0.0239(9) 0.0282(11) 0.0088(8) 0.0076(8) 0.0088(8) C14 0.0227(10) 0.0211(9) 0.0260(11) 0.0080(8) 0.0088(8) 0.0077(8) C15 0.0195(9) 0.0216(9) 0.0311(11) 0.0098(8) 0.0053(8) 0.0067(8) C16 0.0279(11) 0.0301(10) 0.0323(12) 0.0123(9) 0.0100(9) 0.0141(9) C17 0.0331(12) 0.0360(12) 0.0308(12) 0.0143(9) 0.0058(9) 0.0128(10) C18 0.0308(12) 0.0425(13) 0.0382(14) 0.0180(10) 0.0019(10) 0.0176(10) C19 0.0358(13) 0.0545(15) 0.0421(15) 0.0194(12) 0.0111(11) 0.0308(12) C20 0.0299(11) 0.0478(13) 0.0346(13) 0.0164(10) 0.0116(9) 0.0229(10) C21 0.0197(9) 0.0265(10) 0.0335(12) 0.0135(9) 0.0061(8) 0.0084(8) C22 0.0315(11) 0.0274(10) 0.0344(13) 0.0103(9) 0.0083(9) 0.0100(9) C23 0.0319(12) 0.0261(11) 0.0477(15) 0.0138(10) 0.0081(10) 0.0091(9) C24 0.0287(12) 0.0389(12) 0.0512(16) 0.0288(11) 0.0121(10) 0.0117(10) C25 0.0431(14) 0.0446(13) 0.0366(14) 0.0213(11) 0.0165(11) 0.0166(11) C26 0.0386(13) 0.0294(11) 0.0327(13) 0.0104(9) 0.0101(10) 0.0092(10) C31 0.0246(11) 0.0350(11) 0.0386(13) 0.0190(10) 0.0132(9) 0.0140(9) C32 0.0239(10) 0.0285(10) 0.0381(13) 0.0136(9) 0.0061(9) 0.0055(9) C33 0.0307(12) 0.0364(12) 0.0451(15) 0.0163(10) 0.0116(10) 0.0139(10) C34 0.0427(14) 0.0322(12) 0.0463(15) 0.0149(11) 0.0193(11) 0.0142(11) C35 0.0378(14) 0.0299(12) 0.0599(18) 0.0126(12) 0.0050(12) 0.0014(11) C36 0.0293(14) 0.0386(15) 0.141(4) 0.0186(18) -0.0191(17) 0.0048(12) C37 0.0278(13) 0.0308(13) 0.119(3) 0.0151(15) -0.0029(15) 0.0094(11) _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 1.907(2) . ? Cu1 C31 1.917(2) . ? Cu1 N2 2.0367(18) . ? Cu1 N3 2.0530(18) . ? N1 C1 1.164(3) . ? N1 C2 1.403(3) . ? N2 C8 1.294(3) . ? N2 C21 1.437(3) . ? N3 C14 1.308(3) . ? N3 C15 1.429(3) . ? N4 C31 1.164(3) . ? N4 C32 1.407(3) . ? C2 C7 1.383(3) . ? C2 C3 1.388(3) . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.376(4) . ? C4 H4 0.9500 . ? C5 C6 1.379(4) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.426(3) . ? C8 H8 0.9500 . ? C9 C10 1.415(3) . ? C9 C13 1.447(3) . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 C13 1.421(3) . ? C12 H12 0.9500 . ? C13 C14 1.416(3) . ? C14 H14 0.9500 . ? C15 C16 1.386(3) . ? C15 C20 1.397(3) . ? C16 C17 1.389(3) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 C19 1.378(4) . ? C18 H18 0.9500 . ? C19 C20 1.385(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C26 1.388(3) . ? C21 C22 1.390(3) . ? C22 C23 1.394(3) . ? C22 H22 0.9500 . ? C23 C24 1.372(4) . ? C23 H23 0.9500 . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.389(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C32 C37 1.366(3) . ? C32 C33 1.379(3) . ? C33 C34 1.386(3) . ? C33 H33 0.9500 . ? C34 C35 1.364(4) . ? C34 H34 0.9500 . ? C35 C36 1.374(4) . ? C35 H35 0.9500 . ? C36 C37 1.387(4) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? 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 C31 116.95(10) . . ? C1 Cu1 N2 112.01(8) . . ? C31 Cu1 N2 100.67(8) . . ? C1 Cu1 N3 108.15(8) . . ? C31 Cu1 N3 112.54(8) . . ? N2 Cu1 N3 105.87(7) . . ? C1 N1 C2 178.2(2) . . ? C8 N2 C21 115.86(18) . . ? C8 N2 Cu1 130.80(15) . . ? C21 N2 Cu1 113.34(13) . . ? C14 N3 C15 115.20(18) . . ? C14 N3 Cu1 127.28(15) . . ? C15 N3 Cu1 117.05(13) . . ? C31 N4 C32 173.6(2) . . ? N1 C1 Cu1 174.7(2) . . ? C7 C2 C3 122.2(2) . . ? C7 C2 N1 119.5(2) . . ? C3 C2 N1 118.2(2) . . ? C4 C3 C2 117.9(2) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C7 119.9(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C2 C7 C6 118.6(2) . . ? C2 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? N2 C8 C9 129.03(19) . . ? N2 C8 H8 115.5 . . ? C9 C8 H8 115.5 . . ? C10 C9 C8 118.59(19) . . ? C10 C9 C13 106.38(18) . . ? C8 C9 C13 134.93(19) . . ? C11 C10 C9 109.8(2) . . ? C11 C10 H10 125.1 . . ? C9 C10 H10 125.1 . . ? C12 C11 C10 107.75(19) . . ? C12 C11 H11 126.1 . . ? C10 C11 H11 126.1 . . ? C11 C12 C13 109.8(2) . . ? C11 C12 H12 125.1 . . ? C13 C12 H12 125.1 . . ? C14 C13 C12 118.62(19) . . ? C14 C13 C9 135.05(18) . . ? C12 C13 C9 106.19(18) . . ? N3 C14 C13 130.5(2) . . ? N3 C14 H14 114.8 . . ? C13 C14 H14 114.8 . . ? C16 C15 C20 118.5(2) . . ? C16 C15 N3 122.16(19) . . ? C20 C15 N3 119.3(2) . . ? C15 C16 C17 121.3(2) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 119.4(2) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.6(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 120.2(2) . . ? C19 C20 H20 119.9 . . ? C15 C20 H20 119.9 . . ? C26 C21 C22 119.8(2) . . ? C26 C21 N2 119.44(18) . . ? C22 C21 N2 120.8(2) . . ? C21 C22 C23 119.0(2) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C24 C23 C22 121.2(2) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 119.7(2) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C26 119.9(2) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C21 120.3(2) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? N4 C31 Cu1 171.24(19) . . ? C37 C32 C33 121.5(2) . . ? C37 C32 N4 119.7(2) . . ? C33 C32 N4 118.8(2) . . ? C32 C33 C34 118.8(2) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? C35 C34 C33 120.5(2) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 119.8(2) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C35 C36 C37 120.8(3) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C32 C37 C36 118.6(3) . . ? C32 C37 H37 120.7 . . ? C36 C37 H37 120.7 . . ? 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 C31 Cu1 N2 C8 134.6(2) . . . . ? N3 Cu1 N2 C8 17.3(2) . . . . ? C31 Cu1 N2 C21 -45.76(16) . . . . ? N3 Cu1 N2 C21 -163.09(14) . . . . ? C1 Cu1 N3 C14 92.09(18) . . . . ? C31 Cu1 N3 C14 -137.17(17) . . . . ? N2 Cu1 N3 C14 -28.12(18) . . . . ? C1 Cu1 N3 C15 -79.67(15) . . . . ? C31 Cu1 N3 C15 51.07(16) . . . . ? N2 Cu1 N3 C15 160.12(13) . . . . ? C7 C2 C3 C4 0.4(4) . . . . ? N1 C2 C3 C4 -179.3(2) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C3 C2 C7 C6 -0.6(4) . . . . ? N1 C2 C7 C6 179.1(2) . . . . ? C5 C6 C7 C2 0.4(4) . . . . ? C21 N2 C8 C9 -176.5(2) . . . . ? Cu1 N2 C8 C9 3.1(3) . . . . ? N2 C8 C9 C10 165.1(2) . . . . ? N2 C8 C9 C13 -10.7(4) . . . . ? C8 C9 C10 C11 -175.3(2) . . . . ? C13 C9 C10 C11 1.6(3) . . . . ? C9 C10 C11 C12 -1.9(3) . . . . ? C10 C11 C12 C13 1.5(3) . . . . ? C11 C12 C13 C14 -176.88(19) . . . . ? C11 C12 C13 C9 -0.5(3) . . . . ? C10 C9 C13 C14 174.8(2) . . . . ? C8 C9 C13 C14 -9.0(4) . . . . ? C10 C9 C13 C12 -0.7(2) . . . . ? C8 C9 C13 C12 175.5(2) . . . . ? C15 N3 C14 C13 -174.2(2) . . . . ? Cu1 N3 C14 C13 13.9(3) . . . . ? C12 C13 C14 N3 -172.8(2) . . . . ? C9 C13 C14 N3 12.1(4) . . . . ? C14 N3 C15 C16 47.1(3) . . . . ? Cu1 N3 C15 C16 -140.11(17) . . . . ? C14 N3 C15 C20 -134.9(2) . . . . ? Cu1 N3 C15 C20 37.9(2) . . . . ? C20 C15 C16 C17 1.3(3) . . . . ? N3 C15 C16 C17 179.29(19) . . . . ? C15 C16 C17 C18 -0.8(3) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 0.2(4) . . . . ? C18 C19 C20 C15 0.3(4) . . . . ? C16 C15 C20 C19 -1.0(3) . . . . ? N3 C15 C20 C19 -179.1(2) . . . . ? C8 N2 C21 C26 104.0(2) . . . . ? Cu1 N2 C21 C26 -75.7(2) . . . . ? C8 N2 C21 C22 -77.2(3) . . . . ? Cu1 N2 C21 C22 103.1(2) . . . . ? C26 C21 C22 C23 -0.1(3) . . . . ? N2 C21 C22 C23 -178.9(2) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C26 0.5(4) . . . . ? C24 C25 C26 C21 -1.1(4) . . . . ? C22 C21 C26 C25 0.9(4) . . . . ? N2 C21 C26 C25 179.8(2) . . . . ? C37 C32 C33 C34 1.7(4) . . . . ? N4 C32 C33 C34 -176.3(2) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? C33 C34 C35 C36 -2.0(5) . . . . ? C34 C35 C36 C37 1.5(6) . . . . ? C33 C32 C37 C36 -2.3(5) . . . . ? N4 C32 C37 C36 175.7(3) . . . . ? C35 C36 C37 C32 0.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.336 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.058