# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Trevor Hayton' _publ_contact_author_email hayton@chem.ucsb.edu loop_ _publ_author_name J.Scepaniak 'Guang Wu' T.Hayton data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 863473' #TrackingRef '- master ketimine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H30 N4' _chemical_formula_weight 554.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 14.0041(7) _cell_length_b 11.7778(6) _cell_length_c 34.9240(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.959(3) _cell_angle_gamma 90.00 _cell_volume 5756.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13170 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.73 _reflns_number_total 5951 _reflns_number_gt 4638 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5951 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 C21 C 0.13124(9) 0.83849(11) 0.14909(4) 0.0270(3) Uani 1 1 d . . . C22 C 0.06286(10) 0.92238(12) 0.14186(4) 0.0306(3) Uani 1 1 d . . . H22 H 0.0735 0.9778 0.1227 0.037 Uiso 1 1 calc R . . C23 C -0.02008(10) 0.92626(13) 0.16207(4) 0.0329(3) Uani 1 1 d . . . H23 H -0.0666 0.9832 0.1565 0.040 Uiso 1 1 calc R . . C24 C -0.03521(10) 0.84692(13) 0.19039(4) 0.0348(3) Uani 1 1 d . . . H24 H -0.0924 0.8486 0.2042 0.042 Uiso 1 1 calc R . . C25 C 0.03358(10) 0.76497(12) 0.19843(4) 0.0332(3) Uani 1 1 d . . . H25 H 0.0233 0.7117 0.2183 0.040 Uiso 1 1 calc R . . C26 C 0.11701(10) 0.75875(12) 0.17822(4) 0.0278(3) Uani 1 1 d . . . C27 C 0.18491(10) 0.66242(12) 0.18732(4) 0.0299(3) Uani 1 1 d . . . C28 C 0.24923(9) 0.67011(12) 0.22225(4) 0.0277(3) Uani 1 1 d . . . C33 C 0.31297(10) 0.58172(13) 0.23009(4) 0.0356(3) Uani 1 1 d . . . H33 H 0.3159 0.5191 0.2130 0.043 Uiso 1 1 calc R . . C32 C 0.37200(11) 0.58451(14) 0.26257(5) 0.0457(4) Uani 1 1 d . . . H32 H 0.4155 0.5240 0.2677 0.055 Uiso 1 1 calc R . . C31 C 0.36805(12) 0.67478(14) 0.28763(5) 0.0458(4) Uani 1 1 d . . . H31 H 0.4085 0.6760 0.3100 0.055 Uiso 1 1 calc R . . C30 C 0.30565(11) 0.76326(13) 0.28030(4) 0.0379(4) Uani 1 1 d . . . H30 H 0.3030 0.8254 0.2976 0.045 Uiso 1 1 calc R . . C29 C 0.24668(10) 0.76102(12) 0.24750(4) 0.0308(3) Uani 1 1 d . . . H29 H 0.2041 0.8224 0.2423 0.037 Uiso 1 1 calc R . . C41 C 0.30325(10) 0.86458(11) 0.14674(4) 0.0276(3) Uani 1 1 d . . . C42 C 0.30143(10) 0.94031(12) 0.17727(4) 0.0302(3) Uani 1 1 d . . . H42 H 0.2422 0.9721 0.1843 0.036 Uiso 1 1 calc R . . C43 C 0.38449(10) 0.97030(13) 0.19761(4) 0.0351(3) Uani 1 1 d . . . H43 H 0.3816 1.0201 0.2190 0.042 Uiso 1 1 calc R . . C44 C 0.47107(11) 0.92788(13) 0.18683(4) 0.0373(4) Uani 1 1 d . . . H44 H 0.5282 0.9482 0.2006 0.045 Uiso 1 1 calc R . . C45 C 0.47415(10) 0.85526(12) 0.15571(4) 0.0338(3) Uani 1 1 d . . . H45 H 0.5344 0.8288 0.1477 0.041 Uiso 1 1 calc R . . C46 C 0.39118(10) 0.81982(12) 0.13572(4) 0.0291(3) Uani 1 1 d . . . C47 C 0.39978(10) 0.73166(12) 0.10498(4) 0.0330(3) Uani 1 1 d . . . C48 C 0.47485(10) 0.74767(13) 0.07632(4) 0.0333(3) Uani 1 1 d . . . C53 C 0.50521(10) 0.85513(13) 0.06543(4) 0.0355(3) Uani 1 1 d . . . H53 H 0.4797 0.9206 0.0773 0.043 Uiso 1 1 calc R . . C52 C 0.57251(11) 0.86752(15) 0.03743(5) 0.0444(4) Uani 1 1 d . . . H52 H 0.5915 0.9413 0.0298 0.053 Uiso 1 1 calc R . . C51 C 0.61188(11) 0.77346(17) 0.02075(5) 0.0497(5) Uani 1 1 d . . . H51 H 0.6580 0.7822 0.0017 0.060 Uiso 1 1 calc R . . C50 C 0.58408(12) 0.66641(16) 0.03183(5) 0.0496(5) Uani 1 1 d . . . H50 H 0.6122 0.6015 0.0207 0.060 Uiso 1 1 calc R . . C49 C 0.51541(11) 0.65287(14) 0.05916(4) 0.0428(4) Uani 1 1 d . . . H49 H 0.4958 0.5788 0.0662 0.051 Uiso 1 1 calc R . . C1 C 0.20579(9) 0.85371(11) 0.08652(4) 0.0268(3) Uani 1 1 d . . . C2 C 0.26477(10) 0.93073(12) 0.06871(4) 0.0297(3) Uani 1 1 d . . . H2 H 0.3088 0.9746 0.0838 0.036 Uiso 1 1 calc R . . C3 C 0.26058(10) 0.94483(12) 0.02923(4) 0.0330(3) Uani 1 1 d . . . H3 H 0.3027 0.9967 0.0176 0.040 Uiso 1 1 calc R . . C4 C 0.19543(10) 0.88384(13) 0.00670(4) 0.0346(3) Uani 1 1 d . . . H4 H 0.1928 0.8929 -0.0203 0.041 Uiso 1 1 calc R . . C5 C 0.13438(10) 0.80955(12) 0.02430(4) 0.0326(3) Uani 1 1 d . . . H5 H 0.0886 0.7688 0.0090 0.039 Uiso 1 1 calc R . . C6 C 0.13803(10) 0.79262(12) 0.06384(4) 0.0288(3) Uani 1 1 d . . . C7 C 0.07387(10) 0.70448(12) 0.08024(4) 0.0307(3) Uani 1 1 d . . . C8 C -0.02785(10) 0.73314(12) 0.08669(4) 0.0299(3) Uani 1 1 d . . . C13 C -0.08190(11) 0.66733(12) 0.11114(4) 0.0359(3) Uani 1 1 d . . . H13 H -0.0542 0.6020 0.1230 0.043 Uiso 1 1 calc R . . C12 C -0.17527(12) 0.69604(13) 0.11829(4) 0.0404(4) Uani 1 1 d . . . H12 H -0.2109 0.6510 0.1353 0.048 Uiso 1 1 calc R . . C11 C -0.21717(11) 0.79006(13) 0.10086(4) 0.0395(4) Uani 1 1 d . . . H11 H -0.2815 0.8093 0.1057 0.047 Uiso 1 1 calc R . . C10 C -0.16481(11) 0.85579(13) 0.07642(4) 0.0366(3) Uani 1 1 d . . . H10 H -0.1934 0.9200 0.0642 0.044 Uiso 1 1 calc R . . C9 C -0.07070(10) 0.82826(12) 0.06965(4) 0.0336(3) Uani 1 1 d . . . H9 H -0.0349 0.8748 0.0532 0.040 Uiso 1 1 calc R . . N1 N 0.21547(8) 0.83400(9) 0.12701(3) 0.0270(3) Uani 1 1 d . . . N47 N 0.34875(10) 0.64170(11) 0.10318(4) 0.0406(3) Uani 1 1 d . . . N7 N 0.10472(10) 0.60487(11) 0.08839(3) 0.0358(3) Uani 1 1 d . . . N27 N 0.18586(11) 0.57107(11) 0.16776(4) 0.0443(3) Uani 1 1 d . . . H27 H 0.1423(13) 0.5742(15) 0.1475(6) 0.063(6) Uiso 1 1 d . . . H7 H 0.1679(11) 0.5989(13) 0.0817(4) 0.040(5) Uiso 1 1 d . . . H47 H 0.3082(12) 0.6379(14) 0.1229(5) 0.050(5) 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 C21 0.0328(7) 0.0255(8) 0.0221(6) -0.0013(5) -0.0075(5) -0.0055(6) C22 0.0397(8) 0.0261(8) 0.0251(7) 0.0012(6) -0.0102(6) -0.0036(6) C23 0.0357(8) 0.0320(8) 0.0303(7) -0.0035(6) -0.0102(6) 0.0026(6) C24 0.0368(8) 0.0375(9) 0.0300(7) -0.0048(6) -0.0014(6) -0.0023(7) C25 0.0449(9) 0.0296(8) 0.0248(7) 0.0017(6) -0.0006(6) -0.0025(7) C26 0.0359(8) 0.0256(8) 0.0215(6) -0.0009(5) -0.0070(5) -0.0031(6) C27 0.0410(8) 0.0259(8) 0.0228(6) 0.0047(6) 0.0018(6) -0.0008(6) C28 0.0306(7) 0.0271(8) 0.0255(6) 0.0065(6) 0.0020(5) -0.0028(6) C33 0.0382(8) 0.0291(8) 0.0392(8) 0.0009(6) -0.0029(7) 0.0015(7) C32 0.0426(9) 0.0354(9) 0.0578(10) 0.0033(8) -0.0171(8) 0.0062(7) C31 0.0478(10) 0.0388(10) 0.0491(9) 0.0027(8) -0.0235(8) -0.0034(8) C30 0.0450(9) 0.0331(9) 0.0348(8) -0.0010(7) -0.0089(7) -0.0033(7) C29 0.0339(7) 0.0296(8) 0.0288(7) 0.0040(6) -0.0012(6) 0.0015(6) C41 0.0345(7) 0.0234(7) 0.0244(6) 0.0061(5) -0.0081(6) -0.0057(6) C42 0.0352(8) 0.0273(8) 0.0278(7) 0.0032(6) -0.0029(6) -0.0050(6) C43 0.0444(9) 0.0343(9) 0.0260(7) -0.0023(6) -0.0060(6) -0.0090(7) C44 0.0383(8) 0.0408(9) 0.0319(8) 0.0022(7) -0.0127(6) -0.0072(7) C45 0.0335(8) 0.0338(8) 0.0335(7) 0.0030(6) -0.0083(6) 0.0014(6) C46 0.0366(8) 0.0237(8) 0.0264(7) 0.0049(6) -0.0084(6) -0.0023(6) C47 0.0390(8) 0.0257(8) 0.0332(7) 0.0021(6) -0.0135(6) 0.0039(6) C48 0.0325(8) 0.0344(9) 0.0319(7) -0.0058(6) -0.0130(6) 0.0070(6) C53 0.0317(8) 0.0377(9) 0.0369(8) -0.0096(7) -0.0038(6) -0.0006(7) C52 0.0332(8) 0.0550(11) 0.0450(9) -0.0174(8) 0.0010(7) -0.0083(8) C51 0.0298(8) 0.0711(13) 0.0478(10) -0.0243(9) -0.0047(7) 0.0005(8) C50 0.0432(9) 0.0610(12) 0.0435(9) -0.0238(9) -0.0164(8) 0.0244(9) C49 0.0504(10) 0.0391(10) 0.0374(8) -0.0064(7) -0.0209(7) 0.0143(8) C1 0.0322(7) 0.0239(7) 0.0239(6) 0.0020(5) -0.0053(5) 0.0026(6) C2 0.0303(7) 0.0278(8) 0.0305(7) 0.0039(6) -0.0053(6) 0.0004(6) C3 0.0342(8) 0.0328(8) 0.0321(7) 0.0095(6) 0.0023(6) 0.0035(6) C4 0.0414(8) 0.0383(9) 0.0238(7) 0.0037(6) -0.0025(6) 0.0089(7) C5 0.0381(8) 0.0326(8) 0.0263(7) -0.0005(6) -0.0083(6) 0.0024(7) C6 0.0338(7) 0.0256(8) 0.0266(7) 0.0004(6) -0.0056(6) 0.0012(6) C7 0.0427(8) 0.0270(8) 0.0217(6) -0.0028(6) -0.0109(6) -0.0060(6) C8 0.0388(8) 0.0258(8) 0.0243(6) -0.0029(6) -0.0090(6) -0.0072(6) C13 0.0510(9) 0.0263(8) 0.0298(7) 0.0005(6) -0.0056(7) -0.0058(7) C12 0.0503(10) 0.0334(9) 0.0377(8) 0.0018(7) 0.0036(7) -0.0101(7) C11 0.0417(9) 0.0385(9) 0.0382(8) -0.0035(7) -0.0022(7) -0.0048(7) C10 0.0415(9) 0.0329(9) 0.0347(8) 0.0012(7) -0.0098(6) -0.0029(7) C9 0.0408(8) 0.0304(8) 0.0290(7) 0.0024(6) -0.0085(6) -0.0094(7) N1 0.0312(6) 0.0261(6) 0.0231(5) 0.0033(5) -0.0067(5) -0.0047(5) N47 0.0519(8) 0.0286(7) 0.0408(7) 0.0008(6) -0.0072(7) -0.0017(6) N7 0.0455(8) 0.0278(7) 0.0333(7) -0.0019(5) -0.0087(6) -0.0017(6) N27 0.0714(10) 0.0322(8) 0.0284(7) -0.0007(6) -0.0124(7) 0.0074(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C21 C22 1.3931(19) . ? C21 C26 1.4037(18) . ? C21 N1 1.4322(17) . ? C22 C23 1.380(2) . ? C22 H22 0.9500 . ? C23 C24 1.382(2) . ? C23 H23 0.9500 . ? C24 C25 1.386(2) . ? C24 H24 0.9500 . ? C25 C26 1.3874(19) . ? C25 H25 0.9500 . ? C26 C27 1.5073(19) . ? C27 N27 1.2748(18) . ? C27 C28 1.4940(19) . ? C28 C29 1.3886(19) . ? C28 C33 1.3924(19) . ? C33 C32 1.381(2) . ? C33 H33 0.9500 . ? C32 C31 1.379(2) . ? C32 H32 0.9500 . ? C31 C30 1.378(2) . ? C31 H31 0.9500 . ? C30 C29 1.3893(19) . ? C30 H30 0.9500 . ? C29 H29 0.9500 . ? C41 C42 1.3911(19) . ? C41 C46 1.4053(19) . ? C41 N1 1.4344(16) . ? C42 C43 1.3879(19) . ? C42 H42 0.9500 . ? C43 C44 1.376(2) . ? C43 H43 0.9500 . ? C44 C45 1.385(2) . ? C44 H44 0.9500 . ? C45 C46 1.3987(19) . ? C45 H45 0.9500 . ? C46 C47 1.5014(19) . ? C47 N47 1.2784(19) . ? C47 C48 1.488(2) . ? C48 C53 1.392(2) . ? C48 C49 1.397(2) . ? C53 C52 1.389(2) . ? C53 H53 0.9500 . ? C52 C51 1.376(2) . ? C52 H52 0.9500 . ? C51 C50 1.379(3) . ? C51 H51 0.9500 . ? C50 C49 1.387(2) . ? C50 H50 0.9500 . ? C49 H49 0.9500 . ? C1 C2 1.3880(18) . ? C1 C6 1.4121(18) . ? C1 N1 1.4350(16) . ? C2 C3 1.3879(19) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.3944(18) . ? C5 H5 0.9500 . ? C6 C7 1.4993(19) . ? C7 N7 1.2788(18) . ? C7 C8 1.489(2) . ? C8 C9 1.3946(19) . ? C8 C13 1.3953(19) . ? C13 C12 1.382(2) . ? C13 H13 0.9500 . ? C12 C11 1.385(2) . ? C12 H12 0.9500 . ? C11 C10 1.381(2) . ? C11 H11 0.9500 . ? C10 C9 1.385(2) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? N47 H47 0.909(17) . ? N7 H7 0.925(15) . ? N27 H27 0.919(19) . ? 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 C22 C21 C26 119.49(13) . . ? C22 C21 N1 120.15(12) . . ? C26 C21 N1 120.36(12) . . ? C23 C22 C21 121.06(13) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 119.72(13) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 119.57(14) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 121.70(13) . . ? C24 C25 H25 119.2 . . ? C26 C25 H25 119.2 . . ? C25 C26 C21 118.43(13) . . ? C25 C26 C27 117.95(12) . . ? C21 C26 C27 123.52(12) . . ? N27 C27 C28 118.14(13) . . ? N27 C27 C26 122.71(13) . . ? C28 C27 C26 119.01(12) . . ? C29 C28 C33 118.80(13) . . ? C29 C28 C27 122.51(12) . . ? C33 C28 C27 118.68(12) . . ? C32 C33 C28 120.37(14) . . ? C32 C33 H33 119.8 . . ? C28 C33 H33 119.8 . . ? C31 C32 C33 120.24(15) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C30 C31 C32 120.26(14) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C30 C29 119.60(14) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C28 C29 C30 120.72(13) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C42 C41 C46 119.32(12) . . ? C42 C41 N1 119.43(12) . . ? C46 C41 N1 121.25(12) . . ? C43 C42 C41 121.23(14) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? C44 C43 C42 119.91(13) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 119.37(13) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C44 C45 C46 121.90(14) . . ? C44 C45 H45 119.0 . . ? C46 C45 H45 119.0 . . ? C45 C46 C41 118.17(13) . . ? C45 C46 C47 118.54(13) . . ? C41 C46 C47 123.21(12) . . ? N47 C47 C48 118.60(14) . . ? N47 C47 C46 123.36(14) . . ? C48 C47 C46 117.98(12) . . ? C53 C48 C49 118.48(14) . . ? C53 C48 C47 121.90(13) . . ? C49 C48 C47 119.61(14) . . ? C52 C53 C48 120.59(15) . . ? C52 C53 H53 119.7 . . ? C48 C53 H53 119.7 . . ? C51 C52 C53 120.34(17) . . ? C51 C52 H52 119.8 . . ? C53 C52 H52 119.8 . . ? C52 C51 C50 119.75(16) . . ? C52 C51 H51 120.1 . . ? C50 C51 H51 120.1 . . ? C51 C50 C49 120.50(15) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C49 C48 120.32(16) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C2 C1 C6 118.72(12) . . ? C2 C1 N1 120.64(12) . . ? C6 C1 N1 120.61(12) . . ? C1 C2 C3 121.17(13) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 120.46(13) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 118.76(13) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 121.91(13) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.92(13) . . ? C5 C6 C7 118.37(12) . . ? C1 C6 C7 122.59(11) . . ? N7 C7 C8 119.48(13) . . ? N7 C7 C6 121.19(13) . . ? C8 C7 C6 119.32(12) . . ? C9 C8 C13 118.23(14) . . ? C9 C8 C7 121.17(13) . . ? C13 C8 C7 120.57(13) . . ? C12 C13 C8 120.74(14) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C13 C12 C11 120.39(14) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C10 C11 C12 119.60(15) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C10 C9 120.16(14) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C9 C8 120.87(14) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C21 N1 C41 116.12(10) . . ? C21 N1 C1 118.22(10) . . ? C41 N1 C1 118.90(10) . . ? C47 N47 H47 111.5(11) . . ? C7 N7 H7 109.4(10) . . ? C27 N27 H27 111.1(12) . . ? 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 C26 C21 C22 C23 -2.03(19) . . . . ? N1 C21 C22 C23 178.15(12) . . . . ? C21 C22 C23 C24 1.0(2) . . . . ? C22 C23 C24 C25 0.6(2) . . . . ? C23 C24 C25 C26 -1.3(2) . . . . ? C24 C25 C26 C21 0.3(2) . . . . ? C24 C25 C26 C27 -176.31(12) . . . . ? C22 C21 C26 C25 1.35(19) . . . . ? N1 C21 C26 C25 -178.83(12) . . . . ? C22 C21 C26 C27 177.76(12) . . . . ? N1 C21 C26 C27 -2.42(19) . . . . ? C25 C26 C27 N27 96.81(17) . . . . ? C21 C26 C27 N27 -79.61(19) . . . . ? C25 C26 C27 C28 -78.73(16) . . . . ? C21 C26 C27 C28 104.85(15) . . . . ? N27 C27 C28 C29 -173.45(14) . . . . ? C26 C27 C28 C29 2.29(19) . . . . ? N27 C27 C28 C33 5.40(19) . . . . ? C26 C27 C28 C33 -178.86(12) . . . . ? C29 C28 C33 C32 0.4(2) . . . . ? C27 C28 C33 C32 -178.49(14) . . . . ? C28 C33 C32 C31 0.3(2) . . . . ? C33 C32 C31 C30 -0.5(3) . . . . ? C32 C31 C30 C29 0.0(2) . . . . ? C33 C28 C29 C30 -0.9(2) . . . . ? C27 C28 C29 C30 177.98(13) . . . . ? C31 C30 C29 C28 0.7(2) . . . . ? C46 C41 C42 C43 -1.6(2) . . . . ? N1 C41 C42 C43 178.66(12) . . . . ? C41 C42 C43 C44 2.2(2) . . . . ? C42 C43 C44 C45 -0.1(2) . . . . ? C43 C44 C45 C46 -2.6(2) . . . . ? C44 C45 C46 C41 3.3(2) . . . . ? C44 C45 C46 C47 -173.68(13) . . . . ? C42 C41 C46 C45 -1.13(19) . . . . ? N1 C41 C46 C45 178.64(12) . . . . ? C42 C41 C46 C47 175.66(12) . . . . ? N1 C41 C46 C47 -4.57(19) . . . . ? C45 C46 C47 N47 129.09(15) . . . . ? C41 C46 C47 N47 -47.7(2) . . . . ? C45 C46 C47 C48 -47.89(17) . . . . ? C41 C46 C47 C48 135.33(14) . . . . ? N47 C47 C48 C53 152.72(14) . . . . ? C46 C47 C48 C53 -30.14(19) . . . . ? N47 C47 C48 C49 -26.14(19) . . . . ? C46 C47 C48 C49 150.99(12) . . . . ? C49 C48 C53 C52 1.6(2) . . . . ? C47 C48 C53 C52 -177.28(13) . . . . ? C48 C53 C52 C51 -1.6(2) . . . . ? C53 C52 C51 C50 0.2(2) . . . . ? C52 C51 C50 C49 1.2(2) . . . . ? C51 C50 C49 C48 -1.2(2) . . . . ? C53 C48 C49 C50 -0.2(2) . . . . ? C47 C48 C49 C50 178.71(13) . . . . ? C6 C1 C2 C3 -2.6(2) . . . . ? N1 C1 C2 C3 175.52(13) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C2 C3 C4 C5 0.5(2) . . . . ? C3 C4 C5 C6 -1.4(2) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C4 C5 C6 C7 -175.76(13) . . . . ? C2 C1 C6 C5 1.6(2) . . . . ? N1 C1 C6 C5 -176.47(12) . . . . ? C2 C1 C6 C7 177.58(13) . . . . ? N1 C1 C6 C7 -0.5(2) . . . . ? C5 C6 C7 N7 98.11(16) . . . . ? C1 C6 C7 N7 -77.84(18) . . . . ? C5 C6 C7 C8 -81.15(16) . . . . ? C1 C6 C7 C8 102.90(15) . . . . ? N7 C7 C8 C9 -163.53(13) . . . . ? C6 C7 C8 C9 15.74(18) . . . . ? N7 C7 C8 C13 18.73(19) . . . . ? C6 C7 C8 C13 -162.00(12) . . . . ? C9 C8 C13 C12 -0.2(2) . . . . ? C7 C8 C13 C12 177.64(13) . . . . ? C8 C13 C12 C11 0.8(2) . . . . ? C13 C12 C11 C10 -0.5(2) . . . . ? C12 C11 C10 C9 -0.5(2) . . . . ? C11 C10 C9 C8 1.2(2) . . . . ? C13 C8 C9 C10 -0.8(2) . . . . ? C7 C8 C9 C10 -178.63(12) . . . . ? C22 C21 N1 C41 109.59(13) . . . . ? C26 C21 N1 C41 -70.23(16) . . . . ? C22 C21 N1 C1 -41.33(17) . . . . ? C26 C21 N1 C1 138.86(12) . . . . ? C42 C41 N1 C21 -28.13(17) . . . . ? C46 C41 N1 C21 152.11(12) . . . . ? C42 C41 N1 C1 122.59(13) . . . . ? C46 C41 N1 C1 -57.18(17) . . . . ? C2 C1 N1 C21 130.24(13) . . . . ? C6 C1 N1 C21 -51.68(17) . . . . ? C2 C1 N1 C41 -19.86(18) . . . . ? C6 C1 N1 C41 158.22(12) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.186 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.032 #===end=== data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 863474' #TrackingRef '- master ketimine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[N(ArCNHPh)3Cu][CuCl]' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H38 Cl2 Cu2 N4' _chemical_formula_weight 844.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.800(3) _cell_length_b 13.950(4) _cell_length_c 14.453(4) _cell_angle_alpha 101.020(9) _cell_angle_beta 97.408(9) _cell_angle_gamma 94.634(11) _cell_volume 1911.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.292 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6516 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23930 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 26.73 _reflns_number_total 8137 _reflns_number_gt 7543 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+1.1451P] 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 8137 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 -0.025156(18) 0.708824(13) 0.719040(12) 0.01565(6) Uani 1 1 d . . . Cu2 Cu -0.308083(19) 0.753730(15) 0.711056(13) 0.02133(6) Uani 1 1 d . . . Cl2 Cl -0.27603(4) 0.64964(3) 0.79687(3) 0.02871(9) Uani 1 1 d . . . N47 N 0.06993(13) 0.61565(9) 0.77829(9) 0.0175(2) Uani 1 1 d . . . H47 H 0.0224 0.5578 0.7710 0.021 Uiso 1 1 calc R . . Cl1 Cl -0.33554(5) 0.85202(3) 0.61850(3) 0.03169(10) Uani 1 1 d . . . N1 N 0.22577(12) 0.76605(9) 0.68995(8) 0.0131(2) Uani 1 1 d . . . N27 N -0.06652(12) 0.71168(9) 0.58541(9) 0.0154(2) Uani 1 1 d . . . H27 H -0.1466 0.7319 0.5675 0.018 Uiso 1 1 calc R . . C28 C -0.03574(15) 0.70080(10) 0.42059(10) 0.0150(3) Uani 1 1 d . . . C53 C 0.15619(17) 0.50972(13) 0.93615(13) 0.0271(4) Uani 1 1 d . . . H53 H 0.0700 0.5344 0.9440 0.033 Uiso 1 1 calc R . . C52 C 0.20015(18) 0.43946(14) 0.98567(14) 0.0296(4) Uani 1 1 d . . . H52 H 0.1451 0.4170 1.0284 0.036 Uiso 1 1 calc R . . C104 C 0.33807(18) 0.63987(13) 0.22698(13) 0.0271(3) Uani 1 1 d . . . H104 H 0.2913 0.5891 0.1769 0.033 Uiso 1 1 calc R . . C31 C -0.12173(18) 0.73114(12) 0.23810(11) 0.0230(3) Uani 1 1 d . . . H31 H -0.1508 0.7417 0.1759 0.028 Uiso 1 1 calc R . . C11 C 0.0227(2) 1.18292(12) 0.98684(12) 0.0290(4) Uani 1 1 d . . . H11 H 0.0144 1.2395 1.0333 0.035 Uiso 1 1 calc R . . C102 C 0.44592(17) 0.69577(13) 0.38927(12) 0.0254(3) Uani 1 1 d . . . H102 H 0.4734 0.6826 0.4507 0.030 Uiso 1 1 calc R . . C107 C 0.4673(2) 0.91122(14) 0.26511(14) 0.0339(4) Uani 1 1 d . . . H108 H 0.5678 0.9253 0.2698 0.051 Uiso 1 1 calc R . . H109 H 0.4329 0.9598 0.3125 0.051 Uiso 1 1 calc R . . H107 H 0.4233 0.9146 0.2011 0.051 Uiso 1 1 calc R . . C106 C 0.43332(17) 0.81015(12) 0.28332(12) 0.0232(3) Uani 1 1 d . . . C7 C 0.05735(15) 0.92381(11) 0.78084(10) 0.0161(3) Uani 1 1 d . . . C49 C 0.36255(16) 0.50631(11) 0.86251(11) 0.0196(3) Uani 1 1 d . . . H49 H 0.4193 0.5298 0.8213 0.023 Uiso 1 1 calc R . . C42 C 0.40067(15) 0.86521(11) 0.81351(11) 0.0186(3) Uani 1 1 d . . . H42 H 0.4137 0.9079 0.7707 0.022 Uiso 1 1 calc R . . C13 C 0.16518(18) 1.07436(12) 0.90268(12) 0.0232(3) Uani 1 1 d . . . H13 H 0.2544 1.0572 0.8916 0.028 Uiso 1 1 calc R . . C26 C 0.13712(14) 0.64190(10) 0.54148(10) 0.0137(3) Uani 1 1 d . . . C10 C -0.0949(2) 1.12770(14) 0.93344(13) 0.0330(4) Uani 1 1 d . . . H10 H -0.1838 1.1464 0.9435 0.040 Uiso 1 1 calc R . . C47 C 0.19180(15) 0.62411(11) 0.82691(10) 0.0160(3) Uani 1 1 d . . . C45 C 0.37093(16) 0.74026(11) 0.93625(11) 0.0186(3) Uani 1 1 d . . . H45 H 0.3634 0.6963 0.9785 0.022 Uiso 1 1 calc R . . C24 C 0.26859(15) 0.50393(11) 0.49493(11) 0.0177(3) Uani 1 1 d . . . H24 H 0.2787 0.4451 0.4520 0.021 Uiso 1 1 calc R . . C6 C 0.12907(15) 0.92696(11) 0.69675(10) 0.0154(3) Uani 1 1 d . . . C5 C 0.11567(16) 1.00974(11) 0.65626(11) 0.0200(3) Uani 1 1 d . . . H5 H 0.0680 1.0610 0.6860 0.024 Uiso 1 1 calc R . . C43 C 0.47851(16) 0.88719(12) 0.90352(12) 0.0224(3) Uani 1 1 d . . . H43 H 0.5425 0.9447 0.9221 0.027 Uiso 1 1 calc R . . C2 C 0.26227(15) 0.86471(11) 0.57205(10) 0.0169(3) Uani 1 1 d . . . H2 H 0.3156 0.8161 0.5440 0.020 Uiso 1 1 calc R . . C44 C 0.46246(16) 0.82501(12) 0.96606(11) 0.0220(3) Uani 1 1 d . . . H44 H 0.5134 0.8401 1.0285 0.026 Uiso 1 1 calc R . . C29 C 0.06163(16) 0.71890(12) 0.36201(11) 0.0195(3) Uani 1 1 d . . . H29 H 0.1575 0.7205 0.3841 0.023 Uiso 1 1 calc R . . C12 C 0.1523(2) 1.15572(12) 0.97256(12) 0.0274(4) Uani 1 1 d . . . H12 H 0.2328 1.1926 1.0105 0.033 Uiso 1 1 calc R . . C9 C -0.08343(18) 1.04453(13) 0.86472(13) 0.0282(4) Uani 1 1 d . . . H9 H -0.1644 1.0062 0.8289 0.034 Uiso 1 1 calc R . . C101 C 0.47254(16) 0.78984(13) 0.37336(12) 0.0238(3) Uani 1 1 d . . . H101 H 0.5177 0.8408 0.4239 0.029 Uiso 1 1 calc R . . C39 C 0.01822(17) 0.73468(12) 0.27116(12) 0.0240(3) Uani 1 1 d . . . H39 H 0.0847 0.7479 0.2316 0.029 Uiso 1 1 calc R . . C105 C 0.36545(18) 0.73414(13) 0.21122(12) 0.0258(3) Uani 1 1 d . . . H105 H 0.3372 0.7471 0.1498 0.031 Uiso 1 1 calc R . . C23 C 0.36596(15) 0.53938(11) 0.57595(11) 0.0177(3) Uani 1 1 d . . . H23 H 0.4433 0.5045 0.5883 0.021 Uiso 1 1 calc R . . C51 C 0.32443(17) 0.40194(12) 0.97287(12) 0.0237(3) Uani 1 1 d . . . H51 H 0.3551 0.3540 1.0071 0.028 Uiso 1 1 calc R . . C103 C 0.37921(17) 0.62033(13) 0.31599(13) 0.0266(3) Uani 1 1 d . . . H103 H 0.3621 0.5558 0.3271 0.032 Uiso 1 1 calc R . . C25 C 0.15652(15) 0.55630(10) 0.47813(10) 0.0158(3) Uani 1 1 d . . . H25 H 0.0911 0.5335 0.4221 0.019 Uiso 1 1 calc R . . C3 C 0.24399(16) 0.94644(11) 0.53215(11) 0.0204(3) Uani 1 1 d . . . H3 H 0.2822 0.9526 0.4761 0.024 Uiso 1 1 calc R . . C46 C 0.28846(14) 0.71650(10) 0.84573(10) 0.0147(3) Uani 1 1 d . . . C22 C 0.35100(14) 0.62538(11) 0.63885(10) 0.0157(3) Uani 1 1 d . . . H22 H 0.4193 0.6491 0.6931 0.019 Uiso 1 1 calc R . . C8 C 0.04700(16) 1.01794(11) 0.84881(10) 0.0187(3) Uani 1 1 d . . . N7 N -0.00196(13) 0.84382(9) 0.79502(9) 0.0176(2) Uani 1 1 d . . . H7 H -0.0388 0.8503 0.8480 0.021 Uiso 1 1 calc R . . C27 C 0.00746(14) 0.68800(10) 0.51944(10) 0.0139(3) Uani 1 1 d . . . C50 C 0.40392(16) 0.43430(12) 0.91019(12) 0.0224(3) Uani 1 1 d . . . H50 H 0.4876 0.4068 0.8999 0.027 Uiso 1 1 calc R . . C1 C 0.20391(14) 0.85261(10) 0.65239(10) 0.0137(3) Uani 1 1 d . . . C33 C -0.17701(15) 0.69740(11) 0.38624(10) 0.0176(3) Uani 1 1 d . . . H33 H -0.2441 0.6847 0.4256 0.021 Uiso 1 1 calc R . . C48 C 0.23761(15) 0.54446(11) 0.87481(11) 0.0179(3) Uani 1 1 d . . . C4 C 0.16992(17) 1.01919(11) 0.57403(11) 0.0217(3) Uani 1 1 d . . . H4 H 0.1564 1.0751 0.5466 0.026 Uiso 1 1 calc R . . C41 C 0.30328(14) 0.78197(10) 0.78362(10) 0.0144(3) Uani 1 1 d . . . C32 C -0.21935(16) 0.71231(12) 0.29559(11) 0.0211(3) Uani 1 1 d . . . H32 H -0.3152 0.7097 0.2727 0.025 Uiso 1 1 calc R . . C21 C 0.23712(14) 0.67738(10) 0.62354(10) 0.0133(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01543(9) 0.01816(10) 0.01355(9) 0.00402(7) 0.00132(7) 0.00239(7) Cu2 0.01848(10) 0.02731(11) 0.01885(10) 0.00534(8) 0.00383(7) 0.00315(8) Cl2 0.0294(2) 0.0305(2) 0.0273(2) 0.01151(17) 0.00217(16) -0.00046(16) N47 0.0166(6) 0.0178(6) 0.0188(6) 0.0062(5) 0.0022(5) -0.0003(5) Cl1 0.0318(2) 0.0390(2) 0.0304(2) 0.01523(18) 0.00726(17) 0.01635(18) N1 0.0146(5) 0.0121(5) 0.0124(6) 0.0028(4) 0.0007(4) 0.0015(4) N27 0.0123(5) 0.0188(6) 0.0147(6) 0.0031(5) 0.0006(4) 0.0028(5) C28 0.0167(7) 0.0136(6) 0.0143(7) 0.0024(5) 0.0014(5) 0.0026(5) C53 0.0210(8) 0.0330(9) 0.0358(9) 0.0197(8) 0.0120(7) 0.0100(7) C52 0.0261(8) 0.0345(9) 0.0372(10) 0.0234(8) 0.0117(7) 0.0056(7) C104 0.0269(8) 0.0273(8) 0.0270(9) 0.0007(7) 0.0100(7) 0.0035(7) C31 0.0301(8) 0.0261(8) 0.0142(7) 0.0067(6) 0.0009(6) 0.0085(6) C11 0.0554(11) 0.0185(8) 0.0165(8) 0.0042(6) 0.0135(7) 0.0108(7) C102 0.0207(8) 0.0350(9) 0.0256(8) 0.0120(7) 0.0092(6) 0.0108(7) C107 0.0403(10) 0.0274(9) 0.0360(10) 0.0111(8) 0.0058(8) 0.0046(8) C106 0.0217(7) 0.0252(8) 0.0258(8) 0.0069(7) 0.0089(6) 0.0087(6) C7 0.0162(7) 0.0183(7) 0.0137(7) 0.0027(5) 0.0003(5) 0.0054(5) C49 0.0198(7) 0.0215(7) 0.0182(7) 0.0049(6) 0.0040(6) 0.0028(6) C42 0.0185(7) 0.0165(7) 0.0201(7) 0.0038(6) 0.0005(6) 0.0015(6) C13 0.0280(8) 0.0207(8) 0.0210(8) 0.0036(6) 0.0059(6) 0.0011(6) C26 0.0128(6) 0.0150(6) 0.0146(7) 0.0053(5) 0.0030(5) 0.0019(5) C10 0.0397(10) 0.0332(10) 0.0296(9) 0.0034(8) 0.0132(8) 0.0192(8) C47 0.0184(7) 0.0172(7) 0.0138(7) 0.0042(5) 0.0052(5) 0.0034(5) C45 0.0211(7) 0.0210(7) 0.0147(7) 0.0044(6) 0.0023(6) 0.0066(6) C24 0.0203(7) 0.0135(7) 0.0206(7) 0.0029(6) 0.0076(6) 0.0025(5) C6 0.0160(6) 0.0158(7) 0.0137(7) 0.0021(5) 0.0007(5) 0.0018(5) C5 0.0239(7) 0.0172(7) 0.0191(7) 0.0033(6) 0.0024(6) 0.0059(6) C43 0.0213(7) 0.0184(7) 0.0234(8) -0.0005(6) -0.0032(6) -0.0007(6) C2 0.0177(7) 0.0164(7) 0.0165(7) 0.0022(5) 0.0041(5) 0.0009(5) C44 0.0230(8) 0.0230(8) 0.0167(7) -0.0004(6) -0.0040(6) 0.0046(6) C29 0.0166(7) 0.0253(8) 0.0177(7) 0.0059(6) 0.0033(6) 0.0037(6) C12 0.0422(10) 0.0198(8) 0.0190(8) 0.0025(6) 0.0049(7) -0.0019(7) C9 0.0268(8) 0.0303(9) 0.0262(9) 0.0002(7) 0.0038(7) 0.0103(7) C101 0.0192(7) 0.0298(8) 0.0232(8) 0.0043(7) 0.0057(6) 0.0072(6) C39 0.0257(8) 0.0304(9) 0.0194(8) 0.0096(7) 0.0084(6) 0.0047(7) C105 0.0282(8) 0.0312(9) 0.0204(8) 0.0074(7) 0.0073(6) 0.0074(7) C23 0.0160(7) 0.0182(7) 0.0223(7) 0.0087(6) 0.0058(6) 0.0062(5) C51 0.0247(8) 0.0198(7) 0.0281(8) 0.0114(6) -0.0005(6) 0.0029(6) C103 0.0254(8) 0.0257(8) 0.0348(9) 0.0113(7) 0.0153(7) 0.0091(7) C25 0.0161(6) 0.0162(7) 0.0147(7) 0.0025(5) 0.0032(5) -0.0003(5) C3 0.0261(8) 0.0197(7) 0.0164(7) 0.0051(6) 0.0058(6) 0.0007(6) C46 0.0140(6) 0.0158(7) 0.0143(7) 0.0021(5) 0.0027(5) 0.0037(5) C22 0.0136(6) 0.0178(7) 0.0164(7) 0.0058(6) 0.0018(5) 0.0012(5) C8 0.0259(8) 0.0182(7) 0.0136(7) 0.0041(6) 0.0054(6) 0.0059(6) N7 0.0189(6) 0.0212(6) 0.0133(6) 0.0036(5) 0.0038(5) 0.0029(5) C27 0.0134(6) 0.0129(6) 0.0145(7) 0.0024(5) 0.0000(5) 0.0001(5) C50 0.0211(7) 0.0220(8) 0.0244(8) 0.0048(6) 0.0023(6) 0.0065(6) C1 0.0135(6) 0.0138(6) 0.0131(6) 0.0030(5) -0.0002(5) 0.0002(5) C33 0.0165(7) 0.0205(7) 0.0158(7) 0.0034(6) 0.0024(5) 0.0029(6) C48 0.0195(7) 0.0169(7) 0.0176(7) 0.0055(6) 0.0014(6) 0.0012(6) C4 0.0296(8) 0.0169(7) 0.0201(8) 0.0079(6) 0.0028(6) 0.0033(6) C41 0.0136(6) 0.0152(7) 0.0140(7) 0.0018(5) 0.0011(5) 0.0040(5) C32 0.0204(7) 0.0242(8) 0.0180(7) 0.0028(6) -0.0007(6) 0.0076(6) C21 0.0138(6) 0.0132(6) 0.0138(6) 0.0039(5) 0.0046(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N47 1.9252(13) . ? Cu1 N27 1.9302(13) . ? Cu1 N7 1.9697(14) . ? Cu2 Cl2 2.0993(6) . ? Cu2 Cl1 2.0999(6) . ? N47 C47 1.290(2) . ? N47 H47 0.8800 . ? N1 C41 1.4324(18) . ? N1 C21 1.4351(18) . ? N1 C1 1.4355(18) . ? N27 C27 1.2807(19) . ? N27 H27 0.8800 . ? C28 C29 1.394(2) . ? C28 C33 1.403(2) . ? C28 C27 1.485(2) . ? C53 C52 1.384(2) . ? C53 C48 1.393(2) . ? C53 H53 0.9500 . ? C52 C51 1.384(2) . ? C52 H52 0.9500 . ? C104 C103 1.382(3) . ? C104 C105 1.388(2) . ? C104 H104 0.9500 . ? C31 C39 1.387(2) . ? C31 C32 1.387(2) . ? C31 H31 0.9500 . ? C11 C12 1.384(3) . ? C11 C10 1.385(3) . ? C11 H11 0.9500 . ? C102 C101 1.385(2) . ? C102 C103 1.393(3) . ? C102 H102 0.9500 . ? C107 C106 1.502(2) . ? C107 H108 0.9800 . ? C107 H109 0.9800 . ? C107 H107 0.9800 . ? C106 C105 1.392(2) . ? C106 C101 1.397(2) . ? C7 N7 1.280(2) . ? C7 C6 1.486(2) . ? C7 C8 1.501(2) . ? C49 C50 1.381(2) . ? C49 C48 1.393(2) . ? C49 H49 0.9500 . ? C42 C43 1.386(2) . ? C42 C41 1.403(2) . ? C42 H42 0.9500 . ? C13 C12 1.393(2) . ? C13 C8 1.397(2) . ? C13 H13 0.9500 . ? C26 C25 1.401(2) . ? C26 C21 1.418(2) . ? C26 C27 1.4952(19) . ? C10 C9 1.398(2) . ? C10 H10 0.9500 . ? C47 C48 1.487(2) . ? C47 C46 1.495(2) . ? C45 C44 1.386(2) . ? C45 C46 1.412(2) . ? C45 H45 0.9500 . ? C24 C25 1.388(2) . ? C24 C23 1.393(2) . ? C24 H24 0.9500 . ? C6 C5 1.399(2) . ? C6 C1 1.419(2) . ? C5 C4 1.387(2) . ? C5 H5 0.9500 . ? C43 C44 1.381(2) . ? C43 H43 0.9500 . ? C2 C3 1.386(2) . ? C2 C1 1.391(2) . ? C2 H2 0.9500 . ? C44 H44 0.9500 . ? C29 C39 1.391(2) . ? C29 H29 0.9500 . ? C12 H12 0.9500 . ? C9 C8 1.394(2) . ? C9 H9 0.9500 . ? C101 H101 0.9500 . ? C39 H39 0.9500 . ? C105 H105 0.9500 . ? C23 C22 1.390(2) . ? C23 H23 0.9500 . ? C51 C50 1.383(2) . ? C51 H51 0.9500 . ? C103 H103 0.9500 . ? C25 H25 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C46 C41 1.409(2) . ? C22 C21 1.396(2) . ? C22 H22 0.9500 . ? N7 H7 0.8800 . ? C50 H50 0.9500 . ? C33 C32 1.382(2) . ? C33 H33 0.9500 . ? C4 H4 0.9500 . ? C32 H32 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 N47 Cu1 N27 129.00(5) . . ? N47 Cu1 N7 115.05(6) . . ? N27 Cu1 N7 109.61(5) . . ? Cl2 Cu2 Cl1 176.47(2) . . ? Cl2 Cu2 Cu1 70.741(16) . . ? Cl1 Cu2 Cu1 107.173(17) . . ? C47 N47 Cu1 130.64(11) . . ? C47 N47 H47 114.7 . . ? Cu1 N47 H47 114.7 . . ? C41 N1 C21 118.48(11) . . ? C41 N1 C1 115.91(11) . . ? C21 N1 C1 117.59(11) . . ? C27 N27 Cu1 128.45(10) . . ? C27 N27 H27 115.8 . . ? Cu1 N27 H27 115.8 . . ? C29 C28 C33 119.22(13) . . ? C29 C28 C27 121.23(13) . . ? C33 C28 C27 119.53(13) . . ? C52 C53 C48 120.41(15) . . ? C52 C53 H53 119.8 . . ? C48 C53 H53 119.8 . . ? C53 C52 C51 119.90(16) . . ? C53 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? C103 C104 C105 119.62(17) . . ? C103 C104 H104 120.2 . . ? C105 C104 H104 120.2 . . ? C39 C31 C32 120.19(14) . . ? C39 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C12 C11 C10 120.04(16) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C101 C102 C103 120.55(16) . . ? C101 C102 H102 119.7 . . ? C103 C102 H102 119.7 . . ? C106 C107 H108 109.5 . . ? C106 C107 H109 109.5 . . ? H108 C107 H109 109.5 . . ? C106 C107 H107 109.5 . . ? H108 C107 H107 109.5 . . ? H109 C107 H107 109.5 . . ? C105 C106 C101 118.34(15) . . ? C105 C106 C107 121.36(16) . . ? C101 C106 C107 120.28(16) . . ? N7 C7 C6 122.13(13) . . ? N7 C7 C8 118.54(13) . . ? C6 C7 C8 119.24(13) . . ? C50 C49 C48 120.02(14) . . ? C50 C49 H49 120.0 . . ? C48 C49 H49 120.0 . . ? C43 C42 C41 122.12(14) . . ? C43 C42 H42 118.9 . . ? C41 C42 H42 118.9 . . ? C12 C13 C8 120.10(16) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C25 C26 C21 118.89(13) . . ? C25 C26 C27 117.04(13) . . ? C21 C26 C27 124.02(13) . . ? C11 C10 C9 120.26(17) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N47 C47 C48 120.78(13) . . ? N47 C47 C46 122.44(13) . . ? C48 C47 C46 116.54(12) . . ? C44 C45 C46 122.79(14) . . ? C44 C45 H45 118.6 . . ? C46 C45 H45 118.6 . . ? C25 C24 C23 118.69(14) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C5 C6 C1 117.88(13) . . ? C5 C6 C7 115.97(13) . . ? C1 C6 C7 126.10(13) . . ? C4 C5 C6 121.96(14) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C44 C43 C42 119.65(15) . . ? C44 C43 H43 120.2 . . ? C42 C43 H43 120.2 . . ? C3 C2 C1 121.12(14) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C43 C44 C45 118.98(14) . . ? C43 C44 H44 120.5 . . ? C45 C44 H44 120.5 . . ? C39 C29 C28 119.93(14) . . ? C39 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C11 C12 C13 120.20(17) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C9 C10 119.89(17) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C102 C101 C106 120.32(16) . . ? C102 C101 H101 119.8 . . ? C106 C101 H101 119.8 . . ? C31 C39 C29 120.26(15) . . ? C31 C39 H39 119.9 . . ? C29 C39 H39 119.9 . . ? C104 C105 C106 121.50(16) . . ? C104 C105 H105 119.2 . . ? C106 C105 H105 119.2 . . ? C22 C23 C24 120.64(13) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C50 C51 C52 119.92(15) . . ? C50 C51 H51 120.0 . . ? C52 C51 H51 120.0 . . ? C104 C103 C102 119.65(16) . . ? C104 C103 H103 120.2 . . ? C102 C103 H103 120.2 . . ? C24 C25 C26 121.87(13) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C4 C3 C2 119.96(14) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C41 C46 C45 117.55(13) . . ? C41 C46 C47 126.85(13) . . ? C45 C46 C47 115.59(13) . . ? C23 C22 C21 121.04(13) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C9 C8 C13 119.48(15) . . ? C9 C8 C7 119.12(14) . . ? C13 C8 C7 121.13(14) . . ? C7 N7 Cu1 131.26(11) . . ? C7 N7 H7 114.4 . . ? Cu1 N7 H7 114.4 . . ? N27 C27 C28 121.66(13) . . ? N27 C27 C26 119.08(13) . . ? C28 C27 C26 119.19(12) . . ? C49 C50 C51 120.48(15) . . ? C49 C50 H50 119.8 . . ? C51 C50 H50 119.8 . . ? C2 C1 C6 119.57(13) . . ? C2 C1 N1 118.48(13) . . ? C6 C1 N1 121.91(13) . . ? C32 C33 C28 120.50(14) . . ? C32 C33 H33 119.7 . . ? C28 C33 H33 119.7 . . ? C49 C48 C53 119.23(14) . . ? C49 C48 C47 121.47(13) . . ? C53 C48 C47 119.26(14) . . ? C3 C4 C5 119.43(14) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C42 C41 C46 118.83(13) . . ? C42 C41 N1 118.26(13) . . ? C46 C41 N1 122.89(13) . . ? C33 C32 C31 119.89(14) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C22 C21 C26 118.84(13) . . ? C22 C21 N1 119.33(13) . . ? C26 C21 N1 121.82(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.402 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.057 #===end=== data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 863475' #TrackingRef '- master ketimine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[N(ArCNHPh)3Cu]2[CuI3]' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C92 H81 Cu3 I3 N15' _chemical_formula_weight 1968.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 16.9356(8) _cell_length_b 16.9356(8) _cell_length_c 17.9643(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4462.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 1.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6228 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa APEX II' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26538 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 35.19 _reflns_number_total 6797 _reflns_number_gt 4969 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+1.8043P] 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 6797 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75488(12) 0.24059(12) 0.48018(9) 0.0161(3) Uani 1 1 d . . . C2 C 0.83337(12) 0.22476(11) 0.48862(10) 0.0172(3) Uani 1 1 d . . . C3 C 0.88253(13) 0.22389(13) 0.42621(11) 0.0218(3) Uani 1 1 d . . . H3 H 0.8640 0.2304 0.3778 0.026 Uiso 1 1 calc R . . C4 C 0.95856(13) 0.21340(14) 0.43514(12) 0.0260(4) Uani 1 1 d . . . H4 H 0.9912 0.2119 0.3927 0.031 Uiso 1 1 calc R . . C5 C 0.98669(13) 0.20516(13) 0.50574(13) 0.0265(4) Uani 1 1 d . . . H5 H 1.0390 0.1988 0.5115 0.032 Uiso 1 1 calc R . . C6 C 0.93854(14) 0.20621(14) 0.56818(12) 0.0255(4) Uani 1 1 d . . . H6 H 0.9581 0.2012 0.6166 0.031 Uiso 1 1 calc R . . C7 C 0.86147(13) 0.21466(13) 0.55911(10) 0.0210(3) Uani 1 1 d . . . H7 H 0.8275 0.2135 0.6016 0.025 Uiso 1 1 calc R . . C8 C 0.67774(12) 0.19508(11) 0.53418(9) 0.0157(3) Uani 1 1 d . . . C9 C 0.63753(11) 0.23886(11) 0.57277(9) 0.0144(3) Uani 1 1 d . . . C10 C 0.56655(13) 0.18852(13) 0.62279(10) 0.0195(3) Uani 1 1 d . . . H10 H 0.5421 0.2185 0.6514 0.023 Uiso 1 1 calc R . . C11 C 0.53108(13) 0.09489(14) 0.63130(11) 0.0238(4) Uani 1 1 d . . . H11 H 0.4820 0.0614 0.6647 0.029 Uiso 1 1 calc R . . C12 C 0.56737(14) 0.05066(14) 0.59105(12) 0.0257(4) Uani 1 1 d . . . H12 H 0.5419 -0.0135 0.5952 0.031 Uiso 1 1 calc R . . C13 C 0.64164(13) 0.10152(12) 0.54451(11) 0.0209(3) Uani 1 1 d . . . H13 H 0.6685 0.0717 0.5190 0.025 Uiso 1 1 calc R . . C14 C 0.0000 0.0000 0.593(4) 0.24(8) Uani 0.50 3 d SP . . C15 C 0.0000 0.0000 0.670(5) 0.27(7) Uani 0.50 3 d SP . . H15A H -0.0356 0.0272 0.6883 0.401 Uiso 0.17 1 calc PR . . H15B H 0.0628 0.0356 0.6883 0.401 Uiso 0.17 1 calc PR . . H15C H -0.0272 -0.0628 0.6883 0.401 Uiso 0.17 1 calc PR . . C16 C 0.0980(4) 0.2846(3) 0.7500 0.0582(12) Uani 1 2 d S . . C17 C 0.0883(4) 0.3609(4) 0.7500 0.0792(17) Uani 1 2 d S . . H17A H 0.0271 0.3442 0.7327 0.119 Uiso 0.50 1 calc PR . . H17B H 0.1339 0.4071 0.7167 0.119 Uiso 0.50 1 calc PR . . H17C H 0.0973 0.3856 0.8006 0.119 Uiso 0.50 1 calc PR . . C18 C 0.3760(3) 0.2223(4) 0.7500 0.0526(11) Uani 1 2 d S . . C19 C 0.3523(4) 0.2931(3) 0.7500 0.0560(11) Uani 1 2 d S . . H19A H 0.3567 0.3161 0.8008 0.084 Uiso 0.50 1 calc PR . . H19B H 0.2897 0.2682 0.7318 0.084 Uiso 0.50 1 calc PR . . H19C H 0.3942 0.3430 0.7175 0.084 Uiso 0.50 1 calc PR . . Cu2 Cu 0.6667 0.3333 0.41249(2) 0.01664(8) Uani 1 3 d S . . Cu3 Cu 0.6667 0.3333 0.2500 0.02429(13) Uani 1 6 d S . . I1 I 0.545148(14) 0.161674(13) 0.2500 0.02627(6) Uani 1 2 d S . . N1 N 0.75080(10) 0.28912(10) 0.42708(8) 0.0184(3) Uani 1 1 d . . . H1 H 0.7925 0.3045 0.3922 0.022 Uiso 1 1 calc R . . N2 N 0.6667 0.3333 0.56250(13) 0.0145(4) Uani 1 3 d S . . N3 N 0.0000 0.0000 0.5000 0.19(2) Uani 1 6 d S . . N4 N 0.1095(5) 0.2251(4) 0.7500 0.104(2) Uani 1 2 d S . . N5 N 0.3945(4) 0.1652(5) 0.7500 0.0875(18) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0158(7) 0.0140(7) 0.0177(7) -0.0009(5) 0.0023(5) 0.0069(6) C2 0.0151(7) 0.0132(7) 0.0219(7) -0.0003(6) 0.0013(6) 0.0061(6) C3 0.0194(8) 0.0203(8) 0.0255(8) 0.0024(7) 0.0059(6) 0.0098(7) C4 0.0179(9) 0.0226(9) 0.0380(10) 0.0055(8) 0.0101(7) 0.0106(7) C5 0.0134(8) 0.0178(8) 0.0460(11) 0.0009(8) 0.0000(8) 0.0060(7) C6 0.0223(9) 0.0212(9) 0.0322(10) -0.0036(7) -0.0085(7) 0.0102(8) C7 0.0220(8) 0.0193(8) 0.0232(8) -0.0025(6) -0.0013(6) 0.0114(7) C8 0.0147(7) 0.0149(7) 0.0172(6) 0.0015(5) 0.0018(5) 0.0072(6) C9 0.0145(7) 0.0134(7) 0.0149(6) 0.0020(5) 0.0003(5) 0.0068(6) C10 0.0183(8) 0.0220(8) 0.0196(7) 0.0049(6) 0.0040(6) 0.0112(7) C11 0.0198(8) 0.0225(9) 0.0275(9) 0.0110(7) 0.0076(7) 0.0093(7) C12 0.0239(9) 0.0167(8) 0.0352(10) 0.0092(7) 0.0052(8) 0.0091(7) C13 0.0198(8) 0.0167(8) 0.0277(8) 0.0028(6) 0.0034(7) 0.0103(7) C14 0.037(8) 0.037(8) 0.6(2) 0.000 0.000 0.018(4) C15 0.050(8) 0.050(8) 0.7(2) 0.000 0.000 0.025(4) C16 0.066(3) 0.042(2) 0.053(3) 0.000 0.000 0.017(2) C17 0.053(3) 0.074(4) 0.114(5) 0.000 0.000 0.035(3) C18 0.057(3) 0.097(4) 0.0183(13) 0.000 0.000 0.050(3) C19 0.063(3) 0.060(3) 0.040(2) 0.000 0.000 0.027(2) Cu2 0.01766(11) 0.01766(11) 0.01460(15) 0.000 0.000 0.00883(6) Cu3 0.02844(19) 0.02844(19) 0.0160(2) 0.000 0.000 0.01422(10) I1 0.03499(11) 0.02593(10) 0.01613(8) 0.000 0.000 0.01390(8) N1 0.0187(7) 0.0193(7) 0.0178(6) 0.0025(5) 0.0049(5) 0.0100(6) N2 0.0140(7) 0.0140(7) 0.0156(10) 0.000 0.000 0.0070(3) N3 0.026(3) 0.026(3) 0.52(6) 0.000 0.000 0.0129(15) N4 0.191(7) 0.077(4) 0.058(3) 0.000 0.000 0.077(4) N5 0.131(5) 0.167(5) 0.0290(17) 0.000 0.000 0.123(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.283(2) . ? C1 C2 1.489(2) . ? C1 C8 1.495(2) . ? C2 C7 1.393(3) . ? C2 C3 1.401(2) . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C7 1.392(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.397(2) . ? C8 C9 1.414(2) . ? C9 C10 1.398(2) . ? C9 N2 1.4310(16) . ? C10 C11 1.395(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.393(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.38(14) . ? C14 N3 1.67(8) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N4 1.118(7) . ? C16 C17 1.382(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N5 1.155(6) . ? C18 C19 1.443(7) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? Cu2 N1 1.9304(16) . ? Cu2 N1 1.9304(16) 3_665 ? Cu2 N1 1.9304(16) 2_655 ? Cu2 N1 1.9304(16) 2_655 ? Cu2 Cu3 2.9190(4) . ? Cu3 I1 2.5892(2) 2_655 ? Cu3 I1 2.5892(2) 3_665 ? Cu3 I1 2.5892(2) . ? Cu3 Cu2 2.9190(4) 10_556 ? N1 H1 0.8800 . ? N2 C9 1.4310(17) 2_655 ? N2 C9 1.4310(16) 3_665 ? N3 C14 1.67(8) 7_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.99(15) . . ? N1 C1 C8 119.96(16) . . ? C2 C1 C8 118.02(15) . . ? C7 C2 C3 119.00(17) . . ? C7 C2 C1 120.33(15) . . ? C3 C2 C1 120.60(16) . . ? C4 C3 C2 120.05(19) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.26(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.19(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 119.50(19) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 120.96(18) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C13 C8 C9 118.52(16) . . ? C13 C8 C1 116.43(15) . . ? C9 C8 C1 125.01(15) . . ? C10 C9 C8 119.21(15) . . ? C10 C9 N2 118.39(15) . . ? C8 C9 N2 122.40(15) . . ? C11 C10 C9 120.92(17) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.12(17) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.10(18) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C8 121.94(17) . . ? C12 C13 H13 119.0 . . ? C8 C13 H13 119.0 . . ? C15 C14 N3 180.000(15) . . ? 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 . . ? N4 C16 C17 177.2(7) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 C19 179.6(6) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 Cu2 N1 118.19(2) . 3_665 ? N1 Cu2 N1 118.19(2) . 2_655 ? N1 Cu2 N1 118.19(2) 3_665 2_655 ? N1 Cu2 N1 118.19(2) . 2_655 ? N1 Cu2 N1 118.19(2) 3_665 2_655 ? N1 Cu2 N1 0.00(13) 2_655 2_655 ? N1 Cu2 Cu3 97.80(5) . . ? N1 Cu2 Cu3 97.80(5) 3_665 . ? N1 Cu2 Cu3 97.80(5) 2_655 . ? N1 Cu2 Cu3 97.80(5) 2_655 . ? I1 Cu3 I1 120.0 2_655 3_665 ? I1 Cu3 I1 120.0 2_655 . ? I1 Cu3 I1 120.0 3_665 . ? I1 Cu3 Cu2 90.0 2_655 . ? I1 Cu3 Cu2 90.0 3_665 . ? I1 Cu3 Cu2 90.0 . . ? I1 Cu3 Cu2 90.0 2_655 10_556 ? I1 Cu3 Cu2 90.0 3_665 10_556 ? I1 Cu3 Cu2 90.0 . 10_556 ? Cu2 Cu3 Cu2 180.0 . 10_556 ? C1 N1 Cu2 129.49(13) . . ? C1 N1 H1 115.3 . . ? Cu2 N1 H1 115.3 . . ? C9 N2 C9 118.36(5) . 2_655 ? C9 N2 C9 118.36(5) . 3_665 ? C9 N2 C9 118.36(5) 2_655 3_665 ? C14 N3 C14 180.000(8) . 7_556 ? 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 C1 C2 C7 147.56(18) . . . . ? C8 C1 C2 C7 -34.7(2) . . . . ? N1 C1 C2 C3 -29.5(3) . . . . ? C8 C1 C2 C3 148.16(17) . . . . ? C7 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C4 176.90(17) . . . . ? C2 C3 C4 C5 -1.0(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C5 C6 C7 C2 -1.9(3) . . . . ? C3 C2 C7 C6 1.7(3) . . . . ? C1 C2 C7 C6 -175.47(17) . . . . ? N1 C1 C8 C13 127.28(19) . . . . ? C2 C1 C8 C13 -50.5(2) . . . . ? N1 C1 C8 C9 -50.4(2) . . . . ? C2 C1 C8 C9 131.84(18) . . . . ? C13 C8 C9 C10 3.4(3) . . . . ? C1 C8 C9 C10 -178.96(16) . . . . ? C13 C8 C9 N2 -176.48(17) . . . . ? C1 C8 C9 N2 1.2(3) . . . . ? C8 C9 C10 C11 -4.3(3) . . . . ? N2 C9 C10 C11 175.57(17) . . . . ? C9 C10 C11 C12 1.3(3) . . . . ? C10 C11 C12 C13 2.5(3) . . . . ? C11 C12 C13 C8 -3.4(3) . . . . ? C9 C8 C13 C12 0.4(3) . . . . ? C1 C8 C13 C12 -177.43(18) . . . . ? N1 Cu2 Cu3 I1 -36.32(5) . . . 2_655 ? N1 Cu2 Cu3 I1 -156.32(5) 3_665 . . 2_655 ? N1 Cu2 Cu3 I1 83.68(5) 2_655 . . 2_655 ? N1 Cu2 Cu3 I1 83.68(5) 2_655 . . 2_655 ? N1 Cu2 Cu3 I1 -156.32(5) . . . 3_665 ? N1 Cu2 Cu3 I1 83.68(5) 3_665 . . 3_665 ? N1 Cu2 Cu3 I1 -36.32(5) 2_655 . . 3_665 ? N1 Cu2 Cu3 I1 -36.32(5) 2_655 . . 3_665 ? N1 Cu2 Cu3 I1 83.68(5) . . . . ? N1 Cu2 Cu3 I1 -36.32(5) 3_665 . . . ? N1 Cu2 Cu3 I1 -156.32(5) 2_655 . . . ? N1 Cu2 Cu3 I1 -156.32(5) 2_655 . . . ? N1 Cu2 Cu3 Cu2 -170(5) . . . 10_556 ? N1 Cu2 Cu3 Cu2 70(5) 3_665 . . 10_556 ? N1 Cu2 Cu3 Cu2 -50(5) 2_655 . . 10_556 ? N1 Cu2 Cu3 Cu2 -50(5) 2_655 . . 10_556 ? C2 C1 N1 Cu2 -170.23(12) . . . . ? C8 C1 N1 Cu2 12.1(3) . . . . ? N1 Cu2 N1 C1 -46.0(2) 3_665 . . . ? N1 Cu2 N1 C1 107.54(14) 2_655 . . . ? N1 Cu2 N1 C1 107.54(14) 2_655 . . . ? Cu3 Cu2 N1 C1 -149.23(16) . . . . ? C10 C9 N2 C9 125.61(16) . . . 2_655 ? C8 C9 N2 C9 -54.5(3) . . . 2_655 ? C10 C9 N2 C9 -29.2(3) . . . 3_665 ? C8 C9 N2 C9 150.67(17) . . . 3_665 ? C15 C14 N3 C14 0.0 . . . 7_556 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 35.19 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.799 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.126 #===end=== data_Compound_4 _database_code_depnum_ccdc_archive 'CCDC 863476' #TrackingRef '- master ketimine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[N(ArCNHPh)3Cu]OTf' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41.50 H33 Cl3 Cu F3 N4 O3 S' _chemical_formula_weight 894.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' Cl Cl 0.1484 0.1585 '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 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 18.3059(5) _cell_length_b 17.9205(5) _cell_length_c 24.6247(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.0330(10) _cell_angle_gamma 90.00 _cell_volume 7837.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3656 _exptl_absorpt_coefficient_mu 0.875 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7792 _exptl_absorpt_correction_T_max 0.8444 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30855 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.28 _reflns_number_total 9698 _reflns_number_gt 8467 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+23.8891P] 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 9698 _refine_ls_number_parameters 515 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75916(10) 0.63674(10) 0.08067(7) 0.0142(3) Uani 1 1 d . . . C2 C 0.72314(11) 0.69937(11) 0.09537(8) 0.0163(4) Uani 1 1 d . . . H2 H 0.6854 0.7236 0.0677 0.020 Uiso 1 1 calc R . . C3 C 0.74131(12) 0.72726(11) 0.14978(8) 0.0197(4) Uani 1 1 d . . . H3 H 0.7150 0.7692 0.1591 0.024 Uiso 1 1 calc R . . C4 C 0.79776(12) 0.69391(12) 0.19030(8) 0.0221(4) Uani 1 1 d . . . H4 H 0.8102 0.7124 0.2276 0.027 Uiso 1 1 calc R . . C5 C 0.83574(12) 0.63313(12) 0.17554(8) 0.0200(4) Uani 1 1 d . . . H5 H 0.8756 0.6113 0.2030 0.024 Uiso 1 1 calc R . . C6 C 0.81740(11) 0.60276(11) 0.12147(8) 0.0156(3) Uani 1 1 d . . . C7 C 0.86078(11) 0.53548(11) 0.11190(8) 0.0161(4) Uani 1 1 d . . . C8 C 0.94277(11) 0.53316(12) 0.13947(8) 0.0190(4) Uani 1 1 d . . . C9 C 0.98854(12) 0.59550(13) 0.14049(9) 0.0250(4) Uani 1 1 d . . . H9 H 0.9672 0.6409 0.1240 0.030 Uiso 1 1 calc R . . C10 C 1.06532(13) 0.59201(15) 0.16549(9) 0.0299(5) Uani 1 1 d . . . H10 H 1.0964 0.6343 0.1650 0.036 Uiso 1 1 calc R . . C11 C 1.09612(12) 0.52644(15) 0.19111(9) 0.0296(5) Uani 1 1 d . . . H11 H 1.1482 0.5243 0.2091 0.036 Uiso 1 1 calc R . . C12 C 1.05119(12) 0.46413(14) 0.19058(9) 0.0273(5) Uani 1 1 d . . . H12 H 1.0726 0.4193 0.2081 0.033 Uiso 1 1 calc R . . C13 C 0.97484(12) 0.46694(13) 0.16452(8) 0.0222(4) Uani 1 1 d . . . H13 H 0.9444 0.4238 0.1637 0.027 Uiso 1 1 calc R . . C27 C 0.73773(11) 0.49921(11) -0.07170(8) 0.0154(3) Uani 1 1 d . . . C28 C 0.72087(11) 0.48252(11) -0.13299(8) 0.0162(4) Uani 1 1 d . . . C29 C 0.70363(12) 0.53968(11) -0.17263(9) 0.0202(4) Uani 1 1 d . . . H29 H 0.7045 0.5902 -0.1608 0.024 Uiso 1 1 calc R . . C30 C 0.68522(12) 0.52276(13) -0.22938(9) 0.0236(4) Uani 1 1 d . . . H30 H 0.6719 0.5616 -0.2562 0.028 Uiso 1 1 calc R . . C31 C 0.68624(12) 0.44918(13) -0.24706(8) 0.0236(4) Uani 1 1 d . . . H31 H 0.6741 0.4378 -0.2859 0.028 Uiso 1 1 calc R . . C32 C 0.70500(12) 0.39246(12) -0.20794(9) 0.0220(4) Uani 1 1 d . . . H32 H 0.7066 0.3423 -0.2200 0.026 Uiso 1 1 calc R . . C33 C 0.72161(11) 0.40872(11) -0.15091(8) 0.0190(4) Uani 1 1 d . . . H33 H 0.7334 0.3695 -0.1242 0.023 Uiso 1 1 calc R . . C26 C 0.79551(11) 0.55743(11) -0.05004(8) 0.0159(3) Uani 1 1 d . . . C25 C 0.85597(12) 0.56037(12) -0.07575(9) 0.0220(4) Uani 1 1 d . . . H25 H 0.8554 0.5280 -0.1064 0.026 Uiso 1 1 calc R . . C24 C 0.91627(12) 0.60821(13) -0.05838(9) 0.0247(4) Uani 1 1 d . . . H24 H 0.9569 0.6075 -0.0761 0.030 Uiso 1 1 calc R . . C23 C 0.91676(11) 0.65742(12) -0.01462(9) 0.0204(4) Uani 1 1 d . . . H23 H 0.9576 0.6910 -0.0023 0.024 Uiso 1 1 calc R . . C22 C 0.85696(11) 0.65688(11) 0.01081(8) 0.0156(3) Uani 1 1 d . . . H22 H 0.8569 0.6914 0.0401 0.019 Uiso 1 1 calc R . . C21 C 0.79678(10) 0.60729(10) -0.00527(7) 0.0138(3) Uani 1 1 d . . . C41 C 0.66303(10) 0.62438(10) -0.00773(7) 0.0137(3) Uani 1 1 d . . . C42 C 0.65189(11) 0.65862(10) -0.06005(8) 0.0150(3) Uani 1 1 d . . . H42 H 0.6943 0.6708 -0.0742 0.018 Uiso 1 1 calc R . . C43 C 0.58021(12) 0.67519(11) -0.09190(8) 0.0192(4) Uani 1 1 d . . . H43 H 0.5739 0.6971 -0.1279 0.023 Uiso 1 1 calc R . . C44 C 0.51782(12) 0.65975(12) -0.07128(8) 0.0219(4) Uani 1 1 d . . . H44 H 0.4687 0.6720 -0.0925 0.026 Uiso 1 1 calc R . . C45 C 0.52823(11) 0.62614(12) -0.01912(8) 0.0196(4) Uani 1 1 d . . . H45 H 0.4855 0.6162 -0.0048 0.024 Uiso 1 1 calc R . . C46 C 0.59964(10) 0.60651(10) 0.01299(8) 0.0152(3) Uani 1 1 d . . . C47 C 0.60217(11) 0.56421(11) 0.06567(8) 0.0163(4) Uani 1 1 d . . . C48 C 0.55392(11) 0.59014(12) 0.10283(8) 0.0186(4) Uani 1 1 d . . . C49 C 0.54619(12) 0.66642(13) 0.11189(9) 0.0227(4) Uani 1 1 d . . . H49 H 0.5681 0.7018 0.0918 0.027 Uiso 1 1 calc R . . C50 C 0.50644(13) 0.69097(14) 0.15030(9) 0.0281(5) Uani 1 1 d . . . H50 H 0.5031 0.7428 0.1574 0.034 Uiso 1 1 calc R . . C51 C 0.47214(13) 0.64022(16) 0.17785(9) 0.0313(5) Uani 1 1 d . . . H51 H 0.4445 0.6570 0.2036 0.038 Uiso 1 1 calc R . . C52 C 0.47779(13) 0.56433(16) 0.16815(10) 0.0311(5) Uani 1 1 d . . . H52 H 0.4532 0.5295 0.1867 0.037 Uiso 1 1 calc R . . C53 C 0.51931(12) 0.53891(13) 0.13133(9) 0.0252(4) Uani 1 1 d . . . H53 H 0.5241 0.4869 0.1256 0.030 Uiso 1 1 calc R . . C401 C 0.79275(12) 0.34026(13) 0.19249(9) 0.0239(4) Uani 1 1 d . . . Cu1 Cu 0.720525(13) 0.469882(13) 0.041622(9) 0.01544(7) Uani 1 1 d . . . F1 F 0.81251(8) 0.41188(8) 0.19537(5) 0.0295(3) Uani 1 1 d . . . F2 F 0.84939(8) 0.30077(10) 0.18184(7) 0.0416(4) Uani 1 1 d . . . F3 F 0.78582(8) 0.32030(9) 0.24353(6) 0.0360(3) Uani 1 1 d . . . N1 N 0.73814(9) 0.61033(9) 0.02395(6) 0.0132(3) Uani 1 1 d . . . N27 N 0.70684(9) 0.46124(9) -0.03886(7) 0.0163(3) Uani 1 1 d . . . H27 H 0.6751 0.4265 -0.0552 0.020 Uiso 1 1 calc R . . N47 N 0.64334(9) 0.50553(9) 0.07668(7) 0.0174(3) Uani 1 1 d . . . H47 H 0.6353 0.4776 0.1040 0.021 Uiso 1 1 calc R . . N7 N 0.82690(9) 0.48086(9) 0.08257(7) 0.0173(3) Uani 1 1 d . . . H7 H 0.8556 0.4422 0.0804 0.021 Uiso 1 1 calc R . . O1 O 0.72500(9) 0.34159(8) 0.08761(6) 0.0239(3) Uani 1 1 d . . . O2 O 0.68816(10) 0.24724(9) 0.14681(8) 0.0310(4) Uani 1 1 d . . . O3 O 0.65422(8) 0.37733(8) 0.15539(6) 0.0206(3) Uani 1 1 d . . . S1 S 0.70499(3) 0.32447(3) 0.13962(2) 0.01753(10) Uani 1 1 d . . . Cl21 Cl 0.88649(3) 0.37620(4) 0.97856(3) 0.03489(14) Uani 1 1 d . . . Cl32 Cl 0.0000 0.73359(6) 0.2500 0.1107(8) Uani 1 2 d SD . . Cl31 Cl 0.0000 0.89089(8) 0.2500 0.1124(8) Uani 1 2 d SD . . C301 C 0.0512(3) 0.8193(3) 0.2412(2) 0.0376(12) Uani 0.50 1 d PD . . C201 C 0.82656(13) 0.30559(13) 0.99287(9) 0.0261(4) Uani 1 1 d . . . H20A H 0.8033 0.2786 0.9579 0.031 Uiso 1 1 calc R . . H20B H 0.7857 0.3285 1.0071 0.031 Uiso 1 1 calc R . . Cl22 Cl 0.87699(4) 0.24189(4) 1.04294(3) 0.04343(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(8) 0.0168(8) 0.0118(8) -0.0003(6) 0.0040(6) -0.0028(7) C2 0.0161(9) 0.0172(8) 0.0158(8) 0.0003(7) 0.0043(7) -0.0003(7) C3 0.0224(10) 0.0196(9) 0.0186(9) -0.0044(7) 0.0080(8) -0.0022(8) C4 0.0259(10) 0.0266(10) 0.0140(9) -0.0041(7) 0.0049(8) -0.0023(8) C5 0.0201(9) 0.0244(10) 0.0139(8) 0.0003(7) 0.0011(7) -0.0010(8) C6 0.0149(8) 0.0183(9) 0.0136(8) 0.0006(7) 0.0030(7) -0.0018(7) C7 0.0146(8) 0.0212(9) 0.0123(8) 0.0038(7) 0.0029(7) 0.0016(7) C8 0.0142(9) 0.0292(10) 0.0133(8) -0.0005(7) 0.0028(7) 0.0019(8) C9 0.0204(10) 0.0330(11) 0.0200(10) -0.0004(8) 0.0016(8) -0.0031(9) C10 0.0190(10) 0.0470(14) 0.0230(10) -0.0065(10) 0.0035(8) -0.0081(10) C11 0.0140(9) 0.0570(16) 0.0169(9) -0.0078(9) 0.0019(7) 0.0034(10) C12 0.0183(10) 0.0447(13) 0.0182(9) 0.0017(9) 0.0030(8) 0.0108(9) C13 0.0175(9) 0.0321(11) 0.0173(9) 0.0024(8) 0.0045(7) 0.0046(8) C27 0.0144(8) 0.0156(8) 0.0158(8) -0.0021(7) 0.0025(7) 0.0025(7) C28 0.0150(8) 0.0184(9) 0.0147(8) -0.0012(7) 0.0029(7) -0.0005(7) C29 0.0222(10) 0.0188(9) 0.0204(9) 0.0014(7) 0.0063(8) 0.0007(8) C30 0.0235(10) 0.0290(11) 0.0181(9) 0.0061(8) 0.0047(8) 0.0026(8) C31 0.0219(10) 0.0351(12) 0.0131(8) -0.0017(8) 0.0028(7) -0.0002(9) C32 0.0236(10) 0.0222(10) 0.0196(9) -0.0054(8) 0.0042(8) -0.0009(8) C33 0.0206(9) 0.0187(9) 0.0170(9) -0.0007(7) 0.0032(7) 0.0006(7) C26 0.0155(8) 0.0173(8) 0.0152(8) -0.0014(7) 0.0040(7) -0.0003(7) C25 0.0208(10) 0.0265(10) 0.0208(9) -0.0059(8) 0.0093(8) -0.0014(8) C24 0.0194(10) 0.0330(11) 0.0251(10) -0.0048(9) 0.0118(8) -0.0035(9) C23 0.0165(9) 0.0231(10) 0.0216(9) -0.0021(8) 0.0048(7) -0.0044(7) C22 0.0163(9) 0.0161(8) 0.0141(8) -0.0007(6) 0.0033(7) -0.0007(7) C21 0.0128(8) 0.0155(8) 0.0131(8) 0.0016(6) 0.0034(6) 0.0012(7) C41 0.0135(8) 0.0132(8) 0.0136(8) -0.0023(6) 0.0016(6) 0.0003(6) C42 0.0177(9) 0.0135(8) 0.0137(8) -0.0006(6) 0.0035(7) 0.0003(7) C43 0.0229(10) 0.0195(9) 0.0128(8) -0.0004(7) -0.0002(7) 0.0025(8) C44 0.0172(9) 0.0268(10) 0.0184(9) -0.0010(8) -0.0021(7) 0.0041(8) C45 0.0138(9) 0.0253(10) 0.0197(9) -0.0025(8) 0.0037(7) 0.0011(7) C46 0.0144(8) 0.0163(8) 0.0146(8) -0.0007(6) 0.0029(7) 0.0008(7) C47 0.0134(8) 0.0206(9) 0.0150(8) 0.0000(7) 0.0037(7) -0.0028(7) C48 0.0133(8) 0.0277(10) 0.0153(8) 0.0011(7) 0.0043(7) 0.0010(7) C49 0.0195(10) 0.0283(11) 0.0216(10) 0.0002(8) 0.0075(8) 0.0027(8) C50 0.0241(11) 0.0369(12) 0.0237(10) -0.0047(9) 0.0067(8) 0.0073(9) C51 0.0223(10) 0.0529(15) 0.0206(10) -0.0022(10) 0.0090(8) 0.0073(10) C52 0.0222(11) 0.0489(14) 0.0258(11) 0.0068(10) 0.0130(9) -0.0021(10) C53 0.0198(10) 0.0316(11) 0.0257(10) 0.0033(9) 0.0086(8) -0.0014(8) C401 0.0192(10) 0.0302(11) 0.0206(10) 0.0051(8) 0.0013(8) -0.0015(8) Cu1 0.01547(12) 0.01553(12) 0.01539(11) -0.00022(8) 0.00387(8) 0.00015(8) F1 0.0298(7) 0.0328(7) 0.0235(6) -0.0006(5) 0.0019(5) -0.0156(6) F2 0.0214(7) 0.0522(10) 0.0493(9) 0.0025(7) 0.0051(6) 0.0116(7) F3 0.0337(8) 0.0496(9) 0.0210(6) 0.0152(6) -0.0009(6) -0.0075(7) N1 0.0121(7) 0.0168(7) 0.0107(7) -0.0001(5) 0.0023(6) 0.0001(6) N27 0.0149(7) 0.0154(7) 0.0181(8) -0.0016(6) 0.0028(6) -0.0006(6) N47 0.0173(8) 0.0190(8) 0.0171(7) 0.0028(6) 0.0061(6) -0.0010(6) N7 0.0165(8) 0.0181(8) 0.0168(7) 0.0025(6) 0.0032(6) 0.0029(6) O1 0.0305(8) 0.0234(7) 0.0183(7) -0.0046(6) 0.0066(6) 0.0021(6) O2 0.0323(9) 0.0169(7) 0.0425(10) 0.0000(7) 0.0068(7) -0.0052(6) O3 0.0200(7) 0.0230(7) 0.0187(7) -0.0013(5) 0.0041(5) 0.0017(6) S1 0.0180(2) 0.0151(2) 0.0184(2) -0.00142(16) 0.00229(17) -0.00116(17) Cl21 0.0230(3) 0.0362(3) 0.0450(3) -0.0005(2) 0.0074(2) 0.0027(2) Cl32 0.0915(11) 0.0244(5) 0.1623(17) 0.000 -0.0742(12) 0.000 Cl31 0.1162(15) 0.0388(7) 0.1518(19) 0.000 -0.0263(13) 0.000 C301 0.022(2) 0.057(3) 0.035(3) 0.000(2) 0.0086(19) -0.017(2) C201 0.0245(11) 0.0263(11) 0.0250(10) -0.0039(8) 0.0013(8) 0.0046(9) Cl22 0.0399(4) 0.0456(4) 0.0394(3) 0.0100(3) -0.0008(3) 0.0124(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.393(3) . ? C1 C6 1.413(3) . ? C1 N1 1.436(2) . ? C2 C3 1.393(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.402(3) . ? C5 H5 0.9500 . ? C6 C7 1.494(3) . ? C7 N7 1.283(3) . ? C7 C8 1.490(3) . ? C8 C9 1.393(3) . ? C8 C13 1.399(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(4) . ? C10 H10 0.9500 . ? C11 C12 1.385(4) . ? C11 H11 0.9500 . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C27 N27 1.288(3) . ? C27 C26 1.489(3) . ? C27 C28 1.496(3) . ? C28 C33 1.395(3) . ? C28 C29 1.397(3) . ? C29 C30 1.389(3) . ? C29 H29 0.9500 . ? C30 C31 1.390(3) . ? C30 H30 0.9500 . ? C31 C32 1.385(3) . ? C31 H31 0.9500 . ? C32 C33 1.394(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C26 C25 1.403(3) . ? C26 C21 1.415(3) . ? C25 C24 1.381(3) . ? C25 H25 0.9500 . ? C24 C23 1.391(3) . ? C24 H24 0.9500 . ? C23 C22 1.387(3) . ? C23 H23 0.9500 . ? C22 C21 1.396(3) . ? C22 H22 0.9500 . ? C21 N1 1.431(2) . ? C41 C42 1.397(2) . ? C41 C46 1.413(3) . ? C41 N1 1.429(2) . ? C42 C43 1.388(3) . ? C42 H42 0.9500 . ? C43 C44 1.386(3) . ? C43 H43 0.9500 . ? C44 C45 1.389(3) . ? C44 H44 0.9500 . ? C45 C46 1.399(3) . ? C45 H45 0.9500 . ? C46 C47 1.493(3) . ? C47 N47 1.284(3) . ? C47 C48 1.492(3) . ? C48 C53 1.397(3) . ? C48 C49 1.398(3) . ? C49 C50 1.397(3) . ? C49 H49 0.9500 . ? C50 C51 1.374(4) . ? C50 H50 0.9500 . ? C51 C52 1.389(4) . ? C51 H51 0.9500 . ? C52 C53 1.393(3) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? C401 F1 1.331(3) . ? C401 F2 1.333(3) . ? C401 F3 1.342(2) . ? C401 S1 1.828(2) . ? Cu1 N47 1.9343(17) . ? Cu1 N27 1.9425(17) . ? Cu1 N7 1.9736(17) . ? Cu1 O1 2.5554(16) . ? N27 H27 0.8800 . ? N47 H47 0.8800 . ? N7 H7 0.8800 . ? O1 S1 1.4478(16) . ? O2 S1 1.4382(16) . ? O3 S1 1.4447(15) . ? Cl21 C201 1.765(3) . ? Cl32 C301 1.840(5) . ? Cl32 C301 1.840(5) 2 ? Cl31 C301 1.633(5) . ? Cl31 C301 1.633(5) 2 ? C301 C301 2.023(9) 2 ? C201 Cl22 1.767(2) . ? C201 H20A 0.9900 . ? C201 H20B 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 C2 C1 C6 119.04(17) . . ? C2 C1 N1 119.08(16) . . ? C6 C1 N1 121.83(17) . . ? C3 C2 C1 121.42(18) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C4 C3 C2 120.03(19) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.91(18) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 122.27(19) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.27(18) . . ? C5 C6 C7 116.69(17) . . ? C1 C6 C7 125.03(17) . . ? N7 C7 C8 122.08(18) . . ? N7 C7 C6 120.10(17) . . ? C8 C7 C6 117.77(17) . . ? C9 C8 C13 119.08(19) . . ? C9 C8 C7 121.39(19) . . ? C13 C8 C7 119.53(19) . . ? C10 C9 C8 120.7(2) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 120.1(2) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? N27 C27 C26 121.81(17) . . ? N27 C27 C28 120.89(17) . . ? C26 C27 C28 117.15(16) . . ? C33 C28 C29 119.46(18) . . ? C33 C28 C27 119.55(17) . . ? C29 C28 C27 120.99(17) . . ? C30 C29 C28 120.09(19) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.24(19) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C32 C31 C30 119.88(19) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C33 120.27(19) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C32 C33 C28 120.02(19) . . ? C32 C33 H33 120.0 . . ? C28 C33 H33 120.0 . . ? C25 C26 C21 117.53(18) . . ? C25 C26 C27 115.73(17) . . ? C21 C26 C27 126.70(17) . . ? C24 C25 C26 122.83(19) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? C25 C24 C23 119.22(19) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C22 C23 C24 119.20(19) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C23 C22 C21 122.10(18) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C21 C26 119.07(17) . . ? C22 C21 N1 118.02(16) . . ? C26 C21 N1 122.90(16) . . ? C42 C41 C46 118.93(17) . . ? C42 C41 N1 119.13(16) . . ? C46 C41 N1 121.92(16) . . ? C43 C42 C41 121.45(18) . . ? C43 C42 H42 119.3 . . ? C41 C42 H42 119.3 . . ? C44 C43 C42 120.04(18) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 119.00(18) . . ? C43 C44 H44 120.5 . . ? C45 C44 H44 120.5 . . ? C44 C45 C46 122.11(19) . . ? C44 C45 H45 118.9 . . ? C46 C45 H45 118.9 . . ? C45 C46 C41 118.40(17) . . ? C45 C46 C47 116.52(17) . . ? C41 C46 C47 124.99(17) . . ? N47 C47 C48 122.01(17) . . ? N47 C47 C46 119.49(17) . . ? C48 C47 C46 118.46(17) . . ? C53 C48 C49 119.11(19) . . ? C53 C48 C47 120.76(19) . . ? C49 C48 C47 120.03(18) . . ? C50 C49 C48 120.4(2) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C51 C50 C49 120.1(2) . . ? C51 C50 H50 120.0 . . ? C49 C50 H50 120.0 . . ? C50 C51 C52 120.1(2) . . ? C50 C51 H51 120.0 . . ? C52 C51 H51 120.0 . . ? C51 C52 C53 120.5(2) . . ? C51 C52 H52 119.8 . . ? C53 C52 H52 119.8 . . ? C52 C53 C48 119.8(2) . . ? C52 C53 H53 120.1 . . ? C48 C53 H53 120.1 . . ? F1 C401 F2 107.96(18) . . ? F1 C401 F3 107.05(18) . . ? F2 C401 F3 107.30(18) . . ? F1 C401 S1 111.59(15) . . ? F2 C401 S1 111.65(16) . . ? F3 C401 S1 111.07(15) . . ? N47 Cu1 N27 123.66(7) . . ? N47 Cu1 N7 118.43(7) . . ? N27 Cu1 N7 113.35(7) . . ? N47 Cu1 O1 92.74(6) . . ? N27 Cu1 O1 111.27(6) . . ? N7 Cu1 O1 86.65(6) . . ? C41 N1 C21 118.17(15) . . ? C41 N1 C1 117.92(15) . . ? C21 N1 C1 116.42(15) . . ? C27 N27 Cu1 129.12(14) . . ? C27 N27 H27 115.4 . . ? Cu1 N27 H27 115.4 . . ? C47 N47 Cu1 129.13(14) . . ? C47 N47 H47 115.4 . . ? Cu1 N47 H47 115.4 . . ? C7 N7 Cu1 130.23(14) . . ? C7 N7 H7 114.9 . . ? Cu1 N7 H7 114.9 . . ? S1 O1 Cu1 126.50(8) . . ? O2 S1 O3 115.27(10) . . ? O2 S1 O1 114.87(10) . . ? O3 S1 O1 114.60(9) . . ? O2 S1 C401 103.82(10) . . ? O3 S1 C401 102.62(10) . . ? O1 S1 C401 103.30(10) . . ? C301 Cl32 C301 66.7(3) . 2 ? C301 Cl31 C301 76.6(3) . 2 ? Cl31 C301 Cl32 108.4(2) . . ? Cl31 C301 C301 51.72(16) . 2 ? Cl32 C301 C301 56.64(16) . 2 ? Cl21 C201 Cl22 110.94(13) . . ? Cl21 C201 H20A 109.5 . . ? Cl22 C201 H20A 109.5 . . ? Cl21 C201 H20B 109.5 . . ? Cl22 C201 H20B 109.5 . . ? H20A C201 H20B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.445 _refine_diff_density_min -1.601 _refine_diff_density_rms 0.072 #===end=== data_Compound_5 _database_code_depnum_ccdc_archive 'CCDC 863477' #TrackingRef '- master ketimine.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[N(ArCNHPh)3Cu]PF6' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H38 Cl8 Cu F6 N4 P' _chemical_formula_weight 1102.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 12.7642(6) _cell_length_b 13.1378(6) _cell_length_c 16.1379(7) _cell_angle_alpha 107.663(3) _cell_angle_beta 91.273(3) _cell_angle_gamma 113.713(2) _cell_volume 2328.44(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 1.024 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7487 _exptl_absorpt_correction_T_max 0.8214 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27387 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.28 _reflns_number_total 11511 _reflns_number_gt 8860 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+4.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11511 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7165(2) 0.8248(2) 0.84267(16) 0.0132(5) Uani 1 1 d . . . C2 C 0.7243(2) 0.9207(2) 0.91447(16) 0.0166(5) Uani 1 1 d . . . H2 H 0.6779 0.9605 0.9095 0.020 Uiso 1 1 calc R . . C3 C 0.7981(2) 0.9593(2) 0.99264(17) 0.0199(6) Uani 1 1 d . . . H3 H 0.8034 1.0262 1.0400 0.024 Uiso 1 1 calc R . . C4 C 0.8640(2) 0.9010(2) 1.00208(17) 0.0195(5) Uani 1 1 d . . . H4 H 0.9156 0.9277 1.0554 0.023 Uiso 1 1 calc R . . C5 C 0.8535(2) 0.8025(2) 0.93239(17) 0.0166(5) Uani 1 1 d . . . H5 H 0.8971 0.7609 0.9396 0.020 Uiso 1 1 calc R . . C6 C 0.7809(2) 0.7622(2) 0.85183(16) 0.0142(5) Uani 1 1 d . . . C7 C 0.7811(2) 0.6554(2) 0.78388(16) 0.0144(5) Uani 1 1 d . . . C8 C 0.7912(2) 0.5652(2) 0.81746(16) 0.0160(5) Uani 1 1 d . . . C9 C 0.8824(2) 0.5331(2) 0.80186(17) 0.0192(5) Uani 1 1 d . . . H9 H 0.9402 0.5701 0.7710 0.023 Uiso 1 1 calc R . . C10 C 0.8885(3) 0.4464(2) 0.83178(18) 0.0231(6) Uani 1 1 d . . . H10 H 0.9516 0.4257 0.8224 0.028 Uiso 1 1 calc R . . C11 C 0.8036(3) 0.3906(2) 0.87487(19) 0.0236(6) Uani 1 1 d . . . H11 H 0.8075 0.3304 0.8940 0.028 Uiso 1 1 calc R . . C12 C 0.7120(3) 0.4223(2) 0.89050(18) 0.0220(6) Uani 1 1 d . . . H12 H 0.6532 0.3834 0.9198 0.026 Uiso 1 1 calc R . . C13 C 0.7074(2) 0.5106(2) 0.86311(18) 0.0199(6) Uani 1 1 d . . . H13 H 0.6466 0.5343 0.8755 0.024 Uiso 1 1 calc R . . C41 C 0.5437(2) 0.6799(2) 0.73266(16) 0.0142(5) Uani 1 1 d . . . C42 C 0.5048(2) 0.6209(2) 0.79244(17) 0.0169(5) Uani 1 1 d . . . H42 H 0.5426 0.6573 0.8521 0.020 Uiso 1 1 calc R . . C43 C 0.4115(2) 0.5098(2) 0.76633(19) 0.0209(6) Uani 1 1 d . . . H43 H 0.3881 0.4697 0.8075 0.025 Uiso 1 1 calc R . . C44 C 0.3525(2) 0.4576(2) 0.68050(19) 0.0209(6) Uani 1 1 d . . . H44 H 0.2884 0.3819 0.6625 0.025 Uiso 1 1 calc R . . C45 C 0.3881(2) 0.5168(2) 0.62143(18) 0.0181(5) Uani 1 1 d . . . H45 H 0.3459 0.4819 0.5631 0.022 Uiso 1 1 calc R . . C46 C 0.4846(2) 0.6269(2) 0.64471(16) 0.0144(5) Uani 1 1 d . . . C47 C 0.5202(2) 0.6764(2) 0.57296(16) 0.0154(5) Uani 1 1 d . . . C48 C 0.4293(2) 0.6761(2) 0.51315(17) 0.0158(5) Uani 1 1 d . . . C53 C 0.4397(2) 0.6643(2) 0.42509(17) 0.0187(5) Uani 1 1 d . . . H53 H 0.5028 0.6512 0.4021 0.022 Uiso 1 1 calc R . . C52 C 0.3594(2) 0.6715(2) 0.37114(18) 0.0209(6) Uani 1 1 d . . . H52 H 0.3676 0.6635 0.3114 0.025 Uiso 1 1 calc R . . C51 C 0.2669(2) 0.6902(2) 0.40392(18) 0.0230(6) Uani 1 1 d . . . H51 H 0.2121 0.6959 0.3669 0.028 Uiso 1 1 calc R . . C50 C 0.2544(2) 0.7005(3) 0.49053(19) 0.0234(6) Uani 1 1 d . . . H50 H 0.1907 0.7131 0.5129 0.028 Uiso 1 1 calc R . . C49 C 0.3340(2) 0.6926(2) 0.54483(18) 0.0194(6) Uani 1 1 d . . . H49 H 0.3240 0.6985 0.6040 0.023 Uiso 1 1 calc R . . C21 C 0.6298(2) 0.8898(2) 0.74495(15) 0.0129(5) Uani 1 1 d . . . C22 C 0.5212(2) 0.8898(2) 0.73689(16) 0.0153(5) Uani 1 1 d . . . H22 H 0.4558 0.8267 0.7439 0.018 Uiso 1 1 calc R . . C23 C 0.5066(2) 0.9808(2) 0.71867(18) 0.0184(5) Uani 1 1 d . . . H23 H 0.4313 0.9778 0.7107 0.022 Uiso 1 1 calc R . . C24 C 0.6021(2) 1.0755(2) 0.71218(19) 0.0214(6) Uani 1 1 d . . . H24 H 0.5928 1.1377 0.6995 0.026 Uiso 1 1 calc R . . C25 C 0.7115(2) 1.0791(2) 0.72431(17) 0.0173(5) Uani 1 1 d . . . H25 H 0.7771 1.1462 0.7224 0.021 Uiso 1 1 calc R . . C26 C 0.7281(2) 0.9868(2) 0.73925(16) 0.0142(5) Uani 1 1 d . . . C27 C 0.8491(2) 0.9984(2) 0.74694(16) 0.0146(5) Uani 1 1 d . . . C28 C 0.9432(2) 1.1160(2) 0.80065(17) 0.0163(5) Uani 1 1 d . . . C33 C 1.0488(2) 1.1592(2) 0.77176(19) 0.0223(6) Uani 1 1 d . . . H33 H 1.0612 1.1140 0.7179 0.027 Uiso 1 1 calc R . . C32 C 1.1363(3) 1.2688(3) 0.8218(2) 0.0289(7) Uani 1 1 d . . . H32 H 1.2082 1.2984 0.8016 0.035 Uiso 1 1 calc R . . C31 C 1.1197(3) 1.3348(3) 0.9005(2) 0.0293(7) Uani 1 1 d . . . H31 H 1.1803 1.4091 0.9346 0.035 Uiso 1 1 calc R . . C30 C 1.0148(3) 1.2926(2) 0.92997(19) 0.0262(6) Uani 1 1 d . . . H30 H 1.0035 1.3379 0.9844 0.031 Uiso 1 1 calc R . . C29 C 0.9259(2) 1.1839(2) 0.87968(18) 0.0196(6) Uani 1 1 d . . . H29 H 0.8532 1.1558 0.8992 0.024 Uiso 1 1 calc R . . C101 C 0.8113(5) 0.9990(5) 0.4645(4) 0.096(2) Uani 1 1 d . . . H101 H 0.8232 1.0198 0.4103 0.115 Uiso 1 1 calc R . . H102 H 0.8635 1.0689 0.5149 0.115 Uiso 1 1 calc R . . C301 C 0.3614(3) 0.1977(3) 0.8666(2) 0.0283(7) Uani 1 1 d . . . H302 H 0.3987 0.1508 0.8810 0.034 Uiso 1 1 calc R . . H301 H 0.2767 0.1550 0.8638 0.034 Uiso 1 1 calc R . . C201 C 0.0750(3) 0.4534(3) 0.6057(2) 0.0373(8) Uani 1 1 d . . . H201 H 0.0172 0.4864 0.6107 0.045 Uiso 1 1 calc R . . H202 H 0.1518 0.5191 0.6349 0.045 Uiso 1 1 calc R . . C401 C 0.3504(4) 0.7828(3) 0.9262(2) 0.0438(9) Uani 1 1 d . . . H401 H 0.3217 0.8294 0.9021 0.053 Uiso 1 1 calc R . . H402 H 0.4152 0.7760 0.8960 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.84667(11) 0.88029(10) 0.45548(8) 0.0684(3) Uani 1 1 d . . . Cl2 Cl 0.66535(15) 0.96303(12) 0.48001(9) 0.0858(5) Uani 1 1 d . . . Cl3 Cl 0.38974(7) 0.21123(7) 0.76281(5) 0.03252(17) Uani 1 1 d . . . Cl4 Cl 0.41437(7) 0.33849(7) 0.95092(5) 0.03441(18) Uani 1 1 d . . . Cl5 Cl 0.03825(8) 0.34761(10) 0.65932(6) 0.0453(2) Uani 1 1 d . . . Cl6 Cl 0.07908(8) 0.38949(8) 0.49412(5) 0.0407(2) Uani 1 1 d . . . Cl7 Cl 0.40192(9) 0.85773(8) 1.04066(6) 0.0452(2) Uani 1 1 d . . . Cl8 Cl 0.23822(11) 0.64085(10) 0.90472(7) 0.0596(3) Uani 1 1 d . . . Cu1 Cu 0.75687(3) 0.74617(3) 0.64488(2) 0.01464(7) Uani 1 1 d . . . F1 F 0.2018(2) 0.73193(17) 0.72721(13) 0.0491(6) Uani 1 1 d . . . F2 F 0.27686(14) 0.92395(15) 0.81267(11) 0.0262(4) Uani 1 1 d . . . F3 F 0.20384(17) 0.86837(18) 0.66951(12) 0.0394(5) Uani 1 1 d . . . F4 F 0.11186(18) 0.9348(2) 0.77654(14) 0.0478(6) Uani 1 1 d . . . F5 F 0.03403(18) 0.7400(2) 0.69141(14) 0.0649(8) Uani 1 1 d . . . F6 F 0.10855(17) 0.79602(16) 0.83406(12) 0.0409(5) Uani 1 1 d . . . N1 N 0.64143(18) 0.79330(18) 0.76232(13) 0.0122(4) Uani 1 1 d . . . N47 N 0.62725(19) 0.71573(19) 0.56288(14) 0.0168(5) Uani 1 1 d . . . H47 H 0.6427 0.7301 0.5136 0.020 Uiso 1 1 calc R . . N27 N 0.87081(19) 0.91056(19) 0.70575(14) 0.0161(4) Uani 1 1 d . . . H27 H 0.9443 0.9255 0.7047 0.019 Uiso 1 1 calc R . . N7 N 0.77498(19) 0.64239(19) 0.70180(14) 0.0160(4) Uani 1 1 d . . . H7 H 0.7795 0.5787 0.6670 0.019 Uiso 1 1 calc R . . P1 P 0.15504(6) 0.83211(7) 0.75123(5) 0.02403(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0122(12) 0.0130(12) 0.0134(11) 0.0047(9) 0.0008(9) 0.0043(10) C2 0.0204(14) 0.0151(13) 0.0168(12) 0.0053(10) 0.0033(10) 0.0100(11) C3 0.0264(15) 0.0136(13) 0.0153(12) 0.0015(10) 0.0008(11) 0.0069(11) C4 0.0192(14) 0.0176(13) 0.0163(12) 0.0051(10) -0.0021(10) 0.0037(11) C5 0.0152(13) 0.0154(12) 0.0197(13) 0.0062(10) 0.0000(10) 0.0070(10) C6 0.0134(12) 0.0126(12) 0.0159(12) 0.0043(10) 0.0022(9) 0.0053(10) C7 0.0109(12) 0.0130(12) 0.0185(12) 0.0036(10) 0.0008(9) 0.0059(10) C8 0.0183(13) 0.0132(12) 0.0157(12) 0.0020(10) -0.0012(10) 0.0083(10) C9 0.0193(14) 0.0177(13) 0.0201(13) 0.0047(11) 0.0019(10) 0.0089(11) C10 0.0259(15) 0.0235(15) 0.0248(14) 0.0046(12) 0.0013(12) 0.0180(12) C11 0.0324(16) 0.0173(14) 0.0249(14) 0.0070(11) 0.0008(12) 0.0147(12) C12 0.0256(15) 0.0193(14) 0.0228(14) 0.0086(11) 0.0035(11) 0.0102(12) C13 0.0213(14) 0.0196(14) 0.0211(13) 0.0053(11) 0.0029(11) 0.0120(11) C41 0.0115(12) 0.0127(12) 0.0181(12) 0.0030(10) 0.0018(9) 0.0065(10) C42 0.0144(13) 0.0186(13) 0.0183(12) 0.0053(10) 0.0017(10) 0.0084(11) C43 0.0180(14) 0.0184(14) 0.0295(15) 0.0125(12) 0.0050(11) 0.0079(11) C44 0.0148(13) 0.0132(13) 0.0303(15) 0.0048(11) -0.0002(11) 0.0038(11) C45 0.0141(13) 0.0153(13) 0.0210(13) 0.0021(10) -0.0014(10) 0.0058(10) C46 0.0136(12) 0.0133(12) 0.0168(12) 0.0031(10) 0.0012(10) 0.0079(10) C47 0.0173(13) 0.0123(12) 0.0129(11) -0.0001(9) -0.0006(10) 0.0064(10) C48 0.0146(13) 0.0122(12) 0.0179(12) 0.0028(10) -0.0024(10) 0.0050(10) C53 0.0180(13) 0.0184(13) 0.0176(13) 0.0029(10) 0.0003(10) 0.0085(11) C52 0.0257(15) 0.0161(13) 0.0167(13) 0.0027(10) -0.0025(11) 0.0075(11) C51 0.0228(15) 0.0201(14) 0.0233(14) 0.0045(11) -0.0074(11) 0.0092(12) C50 0.0175(14) 0.0246(15) 0.0263(15) 0.0036(12) -0.0011(11) 0.0112(12) C49 0.0166(13) 0.0206(14) 0.0173(13) 0.0025(11) -0.0009(10) 0.0075(11) C21 0.0149(12) 0.0122(12) 0.0113(11) 0.0017(9) 0.0002(9) 0.0072(10) C22 0.0127(12) 0.0142(12) 0.0168(12) 0.0029(10) 0.0013(9) 0.0055(10) C23 0.0142(13) 0.0197(13) 0.0237(13) 0.0059(11) 0.0014(10) 0.0106(11) C24 0.0219(14) 0.0188(14) 0.0290(15) 0.0100(12) 0.0021(11) 0.0131(12) C25 0.0161(13) 0.0134(12) 0.0209(13) 0.0058(10) 0.0005(10) 0.0050(10) C26 0.0129(12) 0.0154(12) 0.0139(11) 0.0031(10) 0.0005(9) 0.0071(10) C27 0.0140(12) 0.0146(12) 0.0162(12) 0.0073(10) 0.0009(9) 0.0056(10) C28 0.0128(12) 0.0145(12) 0.0216(13) 0.0067(10) -0.0024(10) 0.0055(10) C33 0.0182(14) 0.0188(14) 0.0291(15) 0.0090(12) 0.0013(11) 0.0066(11) C32 0.0143(14) 0.0229(15) 0.0443(19) 0.0147(14) -0.0036(12) 0.0009(12) C31 0.0241(16) 0.0166(14) 0.0385(18) 0.0070(13) -0.0152(13) 0.0030(12) C30 0.0333(17) 0.0192(14) 0.0242(14) 0.0021(11) -0.0094(12) 0.0140(13) C29 0.0189(14) 0.0154(13) 0.0236(14) 0.0050(11) -0.0020(11) 0.0080(11) C101 0.098(5) 0.055(3) 0.099(4) 0.037(3) -0.014(4) -0.010(3) C301 0.0304(17) 0.0212(15) 0.0291(16) 0.0063(12) 0.0014(13) 0.0087(13) C201 0.040(2) 0.0386(19) 0.0328(18) 0.0037(15) 0.0003(15) 0.0230(16) C401 0.065(3) 0.052(2) 0.039(2) 0.0256(18) 0.0220(18) 0.040(2) Cl1 0.0753(8) 0.0534(7) 0.0561(7) 0.0205(5) 0.0118(6) 0.0065(6) Cl2 0.1407(14) 0.0646(8) 0.0626(8) 0.0264(6) 0.0368(8) 0.0497(9) Cl3 0.0391(4) 0.0320(4) 0.0303(4) 0.0085(3) 0.0102(3) 0.0203(4) Cl4 0.0297(4) 0.0312(4) 0.0310(4) -0.0003(3) 0.0040(3) 0.0101(3) Cl5 0.0369(5) 0.0748(7) 0.0435(5) 0.0303(5) 0.0149(4) 0.0349(5) Cl6 0.0392(5) 0.0433(5) 0.0279(4) 0.0066(4) 0.0016(3) 0.0105(4) Cl7 0.0611(6) 0.0474(5) 0.0438(5) 0.0162(4) 0.0080(4) 0.0392(5) Cl8 0.0832(8) 0.0513(6) 0.0461(6) 0.0215(5) 0.0080(5) 0.0273(6) Cu1 0.01355(16) 0.01532(16) 0.01478(15) 0.00342(12) 0.00128(12) 0.00723(13) F1 0.0782(16) 0.0287(11) 0.0416(12) 0.0045(9) 0.0239(11) 0.0290(11) F2 0.0171(8) 0.0278(9) 0.0274(9) 0.0056(7) -0.0009(7) 0.0065(7) F3 0.0399(11) 0.0492(12) 0.0248(9) 0.0149(9) 0.0045(8) 0.0134(10) F4 0.0399(12) 0.0606(14) 0.0506(13) 0.0066(11) -0.0019(10) 0.0385(11) F5 0.0289(12) 0.0764(17) 0.0322(11) -0.0114(11) -0.0049(9) -0.0104(11) F6 0.0414(12) 0.0287(10) 0.0275(10) 0.0000(8) 0.0152(8) -0.0029(9) N1 0.0117(10) 0.0110(10) 0.0134(10) 0.0034(8) -0.0002(8) 0.0049(8) N47 0.0185(11) 0.0178(11) 0.0130(10) 0.0030(9) 0.0026(8) 0.0084(9) N27 0.0110(10) 0.0169(11) 0.0219(11) 0.0072(9) 0.0031(8) 0.0069(9) N7 0.0166(11) 0.0122(10) 0.0179(11) 0.0014(8) 0.0008(8) 0.0076(9) P1 0.0173(4) 0.0240(4) 0.0201(4) -0.0002(3) 0.0025(3) 0.0042(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.396(3) . ? C1 C6 1.410(3) . ? C1 N1 1.439(3) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.379(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.401(3) . ? C5 H5 0.9500 . ? C6 C7 1.497(3) . ? C7 N7 1.280(3) . ? C7 C8 1.490(4) . ? C8 C13 1.393(4) . ? C8 C9 1.394(4) . ? C9 C10 1.393(4) . ? C9 H9 0.9500 . ? C10 C11 1.378(4) . ? C10 H10 0.9500 . ? C11 C12 1.394(4) . ? C11 H11 0.9500 . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C41 C42 1.394(4) . ? C41 C46 1.414(3) . ? C41 N1 1.432(3) . ? C42 C43 1.390(4) . ? C42 H42 0.9500 . ? C43 C44 1.385(4) . ? C43 H43 0.9500 . ? C44 C45 1.381(4) . ? C44 H44 0.9500 . ? C45 C46 1.402(4) . ? C45 H45 0.9500 . ? C46 C47 1.488(4) . ? C47 N47 1.286(3) . ? C47 C48 1.490(4) . ? C48 C53 1.397(4) . ? C48 C49 1.400(4) . ? C53 C52 1.380(4) . ? C53 H53 0.9500 . ? C52 C51 1.385(4) . ? C52 H52 0.9500 . ? C51 C50 1.382(4) . ? C51 H51 0.9500 . ? C50 C49 1.383(4) . ? C50 H50 0.9500 . ? C49 H49 0.9500 . ? C21 C22 1.389(3) . ? C21 C26 1.413(3) . ? C21 N1 1.440(3) . ? C22 C23 1.394(4) . ? C22 H22 0.9500 . ? C23 C24 1.382(4) . ? C23 H23 0.9500 . ? C24 C25 1.385(4) . ? C24 H24 0.9500 . ? C25 C26 1.399(4) . ? C25 H25 0.9500 . ? C26 C27 1.487(3) . ? C27 N27 1.284(3) . ? C27 C28 1.493(3) . ? C28 C33 1.389(4) . ? C28 C29 1.397(4) . ? C33 C32 1.390(4) . ? C33 H33 0.9500 . ? C32 C31 1.379(5) . ? C32 H32 0.9500 . ? C31 C30 1.385(5) . ? C31 H31 0.9500 . ? C30 C29 1.393(4) . ? C30 H30 0.9500 . ? C29 H29 0.9500 . ? C101 Cl1 1.759(6) . ? C101 Cl2 1.772(7) . ? C101 H101 0.9900 . ? C101 H102 0.9900 . ? C301 Cl3 1.767(3) . ? C301 Cl4 1.776(3) . ? C301 H302 0.9900 . ? C301 H301 0.9900 . ? C201 Cl6 1.753(3) . ? C201 Cl5 1.767(4) . ? C201 H201 0.9900 . ? C201 H202 0.9900 . ? C401 Cl8 1.757(4) . ? C401 Cl7 1.771(4) . ? C401 H401 0.9900 . ? C401 H402 0.9900 . ? Cu1 N47 1.923(2) . ? Cu1 N7 1.939(2) . ? Cu1 N27 1.966(2) . ? F1 P1 1.604(2) . ? F2 P1 1.5979(17) . ? F3 P1 1.592(2) . ? F4 P1 1.601(2) . ? F5 P1 1.582(2) . ? F6 P1 1.599(2) . ? N47 H47 0.8800 . ? N27 H27 0.8800 . ? N7 H7 0.8800 . ? 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 C2 C1 C6 119.1(2) . . ? C2 C1 N1 118.2(2) . . ? C6 C1 N1 122.8(2) . . ? C3 C2 C1 121.6(2) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.9(2) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 122.3(2) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C1 117.9(2) . . ? C5 C6 C7 115.1(2) . . ? C1 C6 C7 126.9(2) . . ? N7 C7 C8 121.5(2) . . ? N7 C7 C6 122.4(2) . . ? C8 C7 C6 116.1(2) . . ? C13 C8 C9 119.6(2) . . ? C13 C8 C7 119.8(2) . . ? C9 C8 C7 120.6(2) . . ? C10 C9 C8 119.6(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.6(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C8 120.5(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C42 C41 C46 119.1(2) . . ? C42 C41 N1 119.1(2) . . ? C46 C41 N1 121.8(2) . . ? C43 C42 C41 121.2(2) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? C44 C43 C42 120.1(3) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C45 C44 C43 119.2(2) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? C44 C45 C46 122.1(2) . . ? C44 C45 H45 118.9 . . ? C46 C45 H45 118.9 . . ? C45 C46 C41 118.3(2) . . ? C45 C46 C47 116.8(2) . . ? C41 C46 C47 124.9(2) . . ? N47 C47 C46 119.6(2) . . ? N47 C47 C48 121.8(2) . . ? C46 C47 C48 118.5(2) . . ? C53 C48 C49 118.4(2) . . ? C53 C48 C47 120.8(2) . . ? C49 C48 C47 120.8(2) . . ? C52 C53 C48 120.8(3) . . ? C52 C53 H53 119.6 . . ? C48 C53 H53 119.6 . . ? C53 C52 C51 120.1(3) . . ? C53 C52 H52 120.0 . . ? C51 C52 H52 120.0 . . ? C50 C51 C52 119.9(3) . . ? C50 C51 H51 120.0 . . ? C52 C51 H51 120.0 . . ? C51 C50 C49 120.3(3) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C49 C48 120.4(3) . . ? C50 C49 H49 119.8 . . ? C48 C49 H49 119.8 . . ? C22 C21 C26 119.5(2) . . ? C22 C21 N1 119.7(2) . . ? C26 C21 N1 120.8(2) . . ? C21 C22 C23 121.2(2) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 119.7(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 121.9(2) . . ? C24 C25 H25 119.0 . . ? C26 C25 H25 119.0 . . ? C25 C26 C21 118.1(2) . . ? C25 C26 C27 116.9(2) . . ? C21 C26 C27 125.0(2) . . ? N27 C27 C26 120.4(2) . . ? N27 C27 C28 121.9(2) . . ? C26 C27 C28 117.7(2) . . ? C33 C28 C29 119.4(2) . . ? C33 C28 C27 120.0(2) . . ? C29 C28 C27 120.6(2) . . ? C28 C33 C32 119.9(3) . . ? C28 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C31 C32 C33 120.6(3) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C32 C31 C30 120.0(3) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C30 C29 119.9(3) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C29 C28 120.2(3) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? Cl1 C101 Cl2 111.3(3) . . ? Cl1 C101 H101 109.4 . . ? Cl2 C101 H101 109.4 . . ? Cl1 C101 H102 109.4 . . ? Cl2 C101 H102 109.4 . . ? H101 C101 H102 108.0 . . ? Cl3 C301 Cl4 111.37(17) . . ? Cl3 C301 H302 109.4 . . ? Cl4 C301 H302 109.4 . . ? Cl3 C301 H301 109.4 . . ? Cl4 C301 H301 109.4 . . ? H302 C301 H301 108.0 . . ? Cl6 C201 Cl5 110.88(19) . . ? Cl6 C201 H201 109.5 . . ? Cl5 C201 H201 109.5 . . ? Cl6 C201 H202 109.5 . . ? Cl5 C201 H202 109.5 . . ? H201 C201 H202 108.1 . . ? Cl8 C401 Cl7 111.57(19) . . ? Cl8 C401 H401 109.3 . . ? Cl7 C401 H401 109.3 . . ? Cl8 C401 H402 109.3 . . ? Cl7 C401 H402 109.3 . . ? H401 C401 H402 108.0 . . ? N47 Cu1 N7 128.44(9) . . ? N47 Cu1 N27 119.01(9) . . ? N7 Cu1 N27 110.57(9) . . ? C41 N1 C1 117.7(2) . . ? C41 N1 C21 118.2(2) . . ? C1 N1 C21 115.69(19) . . ? C47 N47 Cu1 126.38(19) . . ? C47 N47 H47 116.8 . . ? Cu1 N47 H47 116.8 . . ? C27 N27 Cu1 126.78(18) . . ? C27 N27 H27 116.6 . . ? Cu1 N27 H27 116.6 . . ? C7 N7 Cu1 127.81(18) . . ? C7 N7 H7 116.1 . . ? Cu1 N7 H7 116.1 . . ? F5 P1 F3 90.98(12) . . ? F5 P1 F2 179.08(13) . . ? F3 P1 F2 89.85(10) . . ? F5 P1 F6 89.96(12) . . ? F3 P1 F6 178.84(12) . . ? F2 P1 F6 89.21(10) . . ? F5 P1 F4 91.33(14) . . ? F3 P1 F4 90.29(12) . . ? F2 P1 F4 89.06(10) . . ? F6 P1 F4 90.37(12) . . ? F5 P1 F1 90.24(14) . . ? F3 P1 F1 89.47(11) . . ? F2 P1 F1 89.38(11) . . ? F6 P1 F1 89.85(11) . . ? F4 P1 F1 178.42(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.004 _refine_diff_density_min -1.334 _refine_diff_density_rms 0.088 #===end===