Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _audit_creation_date 06-05-06 _audit_update_record ? _publ_contact_author_name 'Graham Arthur Bowmaker' _publ_contact_author_address ; Department of Chemistry University of Auckland Private Bag 92019 Auckland 1142 NEW ZEALAND ; _publ_contact_author_email G.BOWMAKER@AUCKLAND.AC.NZ _publ_contact_author_fax (+61)_08_6488_1118 _publ_contact_author_phone (+61)_08_6488_7107 loop_ _publ_author_name 'G. Bowmaker' 'Ekkehardt Hahn' 'John V. Hanna' 'C. Oldham' 'Brian W. Skelton' 'Allan H. White' #===END # Attachment 'cuctb3.cif' data_cuctb3 _database_code_depnum_ccdc_archive 'CCDC 621967' _audit_creation_date 2006-08-24T15:15:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C24 H52 Cl Cu N4 O4' _chemical_formula_moiety 'C20 H36 Cu N4, Cl, 4(C H4 O)' _chemical_formula_weight 559.69 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -c_2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.039(7) _cell_length_b 5.719(5) _cell_length_c 27.779(11) _cell_angle_alpha 90 _cell_angle_beta 102.21(3) _cell_angle_gamma 90 _cell_volume 3422(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 12.6 _cell_measurement_theta_max 18.6 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.018 _exptl_crystal_density_diffrn 1.086 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.745 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min .86 _exptl_absorpt_correction_T_max .98 _exptl_absorpt_process_details ; XTAL absorb ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 336(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; CAD4 diffractometer ; _diffrn_measurement_method '2\q-\w scans' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.1909 _diffrn_reflns_number 2996 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_standards_number 8 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _reflns_number_total 2996 _reflns_number_gt 1820 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Enraf Nonius software' _computing_cell_refinement 'Enraf Nonius software' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_molecular_graphics xtal _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material Shelx #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0415P)^2^] 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_number_reflns 2996 _refine_ls_number_parameters 178 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1159 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.504 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cu Cu 0.5 0.31210(13) 0.25 0.0591(2) Uani 1 2 d S . . Cl Cl 0.31501(18) 0.5434(8) 0.49754(14) 0.2147(19) Uani 0.5 1 d P . . C11 C 0.45742(16) 0.5102(6) 0.29068(13) 0.0628(13) Uani 1 1 d . . . N11 N 0.43142(13) 0.6198(6) 0.31478(10) 0.0720(11) Uani 1 1 d . A . C12 C 0.39961(17) 0.7486(7) 0.34703(14) 0.0559(15) Uani 0.835(3) 1 d P . . C13 C 0.3845(3) 0.5855(11) 0.3839(2) 0.146(3) Uani 0.835(3) 1 d P A 1 H13A H 0.4209 0.4983 0.3986 0.219 Uiso 0.835(3) 1 calc PR A 1 H13B H 0.3526 0.4798 0.3681 0.219 Uiso 0.835(3) 1 calc PR A 1 H13C H 0.3701 0.6721 0.4089 0.219 Uiso 0.835(3) 1 calc PR A 1 C14 C 0.4452(3) 0.9233(12) 0.3763(2) 0.145(3) Uani 0.835(3) 1 d P A 1 H14A H 0.4595 1.0279 0.354 0.218 Uiso 0.835(3) 1 calc PR A 1 H14B H 0.48 0.8408 0.3955 0.218 Uiso 0.835(3) 1 calc PR A 1 H14C H 0.4249 1.0113 0.3978 0.218 Uiso 0.835(3) 1 calc PR A 1 C15 C 0.3491(3) 0.8799(14) 0.31752(19) 0.176(3) Uani 0.835(3) 1 d P A 1 H15A H 0.3321 0.9841 0.3383 0.265 Uiso 0.835(3) 1 calc PR A 1 H15B H 0.3174 0.774 0.3014 0.265 Uiso 0.835(3) 1 calc PR A 1 H15C H 0.3643 0.9688 0.2932 0.265 Uiso 0.835(3) 1 calc PR A 1 C13' C 0.3371(8) 0.621(4) 0.3452(7) 0.050(6) Uiso 0.165(3) 1 d P A 2 H13D H 0.3129 0.7068 0.3641 0.074 Uiso 0.165(3) 1 calc PR A 2 H13E H 0.3451 0.4666 0.3588 0.074 Uiso 0.165(3) 1 calc PR A 2 H13F H 0.3147 0.6097 0.3117 0.074 Uiso 0.165(3) 1 calc PR A 2 C14' C 0.4372(10) 0.672(5) 0.4027(8) 0.078(8) Uiso 0.165(3) 1 d P A 2 H14D H 0.4804 0.708 0.4064 0.118 Uiso 0.165(3) 1 calc PR A 2 H14E H 0.4323 0.5071 0.4071 0.118 Uiso 0.165(3) 1 calc PR A 2 H14F H 0.4206 0.7562 0.4269 0.118 Uiso 0.165(3) 1 calc PR A 2 C15' C 0.4154(11) 0.976(4) 0.3520(9) 0.067(8) Uiso 0.165(3) 1 d P A 2 H15D H 0.4596 0.9898 0.3634 0.101 Uiso 0.165(3) 1 calc PR A 2 H15E H 0.3949 1.048 0.3755 0.101 Uiso 0.165(3) 1 calc PR A 2 H15F H 0.4031 1.0535 0.3208 0.101 Uiso 0.165(3) 1 calc PR A 2 C21 C 0.43872(15) 0.1171(6) 0.20574(12) 0.0606(13) Uani 1 1 d . . . N21 N 0.40238(13) 0.0077(6) 0.17978(10) 0.0663(11) Uani 1 1 d . B . C22 C 0.35584(17) -0.1265(7) 0.14456(15) 0.0822(15) Uani 1 1 d . . . C23 C 0.3919(3) -0.2992(15) 0.1178(3) 0.082(2) Uiso 0.5 1 d P B 3 H23A H 0.4191 -0.3932 0.1416 0.124 Uiso 0.5 1 calc PR B 3 H23B H 0.4158 -0.2126 0.0987 0.124 Uiso 0.5 1 calc PR B 3 H23C H 0.363 -0.3984 0.0963 0.124 Uiso 0.5 1 calc PR B 3 C24 C 0.3171(4) 0.0441(14) 0.1110(3) 0.084(3) Uiso 0.5 1 d P B 3 H24A H 0.2876 -0.0387 0.0865 0.126 Uiso 0.5 1 calc PR B 3 H24B H 0.3432 0.1379 0.0951 0.126 Uiso 0.5 1 calc PR B 3 H24C H 0.2954 0.1431 0.1296 0.126 Uiso 0.5 1 calc PR B 3 C25 C 0.3179(4) -0.2775(14) 0.1741(3) 0.091(3) Uiso 0.5 1 d P B 3 H25A H 0.289 -0.3731 0.1517 0.137 Uiso 0.5 1 calc PR B 3 H25B H 0.2956 -0.1772 0.192 0.137 Uiso 0.5 1 calc PR B 3 H25C H 0.3456 -0.3758 0.1967 0.137 Uiso 0.5 1 calc PR B 3 C23' C 0.2944(5) -0.032(2) 0.1477(4) 0.164(5) Uiso 0.5 1 d P B 4 H23D H 0.2627 -0.1107 0.1242 0.246 Uiso 0.5 1 calc PR B 4 H23E H 0.2931 0.1321 0.1407 0.246 Uiso 0.5 1 calc PR B 4 H23F H 0.2874 -0.0575 0.1803 0.246 Uiso 0.5 1 calc PR B 4 C24' C 0.3673(5) -0.3594(19) 0.1453(4) 0.142(4) Uiso 0.5 1 d P B 4 H24D H 0.3359 -0.436 0.1213 0.213 Uiso 0.5 1 calc PR B 4 H24E H 0.3669 -0.4203 0.1774 0.213 Uiso 0.5 1 calc PR B 4 H24F H 0.4072 -0.3867 0.1378 0.213 Uiso 0.5 1 calc PR B 4 C25' C 0.3558(4) -0.0262(17) 0.0937(3) 0.116(3) Uiso 0.5 1 d P B 4 H25D H 0.3959 -0.0489 0.0861 0.175 Uiso 0.5 1 calc PR B 4 H25E H 0.3466 0.1379 0.0935 0.175 Uiso 0.5 1 calc PR B 4 H25F H 0.3249 -0.1045 0.0696 0.175 Uiso 0.5 1 calc PR B 4 O1 O 0.29745(13) 0.0454(5) 0.44608(10) 0.1072(11) Uani 1 1 d D . . C1 C 0.2637(6) -0.078(2) 0.4468(6) 0.200(7) Uiso 0.5 1 d PD . . C1' C 0.3361(7) 0.155(3) 0.4442(9) 0.350(13) Uiso 0.5 1 d PD . . O2 O 0.4478(4) 0.6065(15) 0.5387(3) 0.195(4) Uiso 0.5 1 d PD . . C2 C 0.4470(8) 0.786(2) 0.5354(6) 0.228(7) Uiso 0.5 1 d PD . . O3 O 0.4451(4) 0.1297(13) 0.4972(3) 0.181(3) Uiso 0.5 1 d PD . . C3 C 0.4406(9) 0.303(2) 0.5002(8) 0.286(9) Uiso 0.5 1 d PD . . 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 Cu 0.0503(3) 0.0791(5) 0.0477(3) 0 0.0094(3) 0 Cl 0.207(4) 0.258(4) 0.173(3) 0.021(3) 0.026(3) 0.044(3) C11 0.069(2) 0.063(3) 0.054(2) -0.003(2) 0.009(2) -0.007(2) N11 0.074(2) 0.079(3) 0.065(2) -0.0057(19) 0.0193(17) 0.0007(19) C12 0.066(2) 0.055(4) 0.057(2) -0.009(2) 0.036(2) 0.017(2) C13 0.205(5) 0.142(6) 0.128(4) 0.014(4) 0.119(4) 0.025(5) C14 0.143(5) 0.156(6) 0.145(6) -0.055(5) 0.050(5) 0.011(5) C15 0.168(5) 0.260(8) 0.109(5) -0.009(5) 0.046(4) 0.126(6) C21 0.059(2) 0.072(3) 0.049(2) -0.005(2) 0.0085(19) 0.000(2) N21 0.0599(19) 0.074(2) 0.059(2) -0.0080(18) -0.0004(17) -0.0038(19) C22 0.070(2) 0.074(3) 0.085(3) -0.005(3) -0.025(2) -0.004(3) O1 0.118(2) 0.128(3) 0.0690(18) 0.0020(19) 0.0062(18) 0.052(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu C21 1.969(3) . ? Cu C21 1.969(3) 2_655 ? Cu C11 1.972(4) . ? Cu C11 1.972(4) 2_655 ? C11 N11 1.154(4) . ? N11 C12 1.450(5) . ? C12 C15' 1.35(3) . ? C12 C15 1.445(7) . ? C12 C13 1.474(7) . ? C12 C14 1.524(7) . ? C12 C13' 1.550(19) . ? C12 C14' 1.65(2) . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C13' H13D 0.96 . ? C13' H13E 0.96 . ? C13' H13F 0.96 . ? C14' H14D 0.96 . ? C14' H14E 0.96 . ? C14' H14F 0.96 . ? C15' H15D 0.96 . ? C15' H15E 0.96 . ? C15' H15F 0.96 . ? C21 N21 1.144(4) . ? N21 C22 1.474(4) . ? C22 C24' 1.354(11) . ? C22 C23' 1.477(11) . ? C22 C24 1.489(8) . ? C22 C25' 1.524(10) . ? C22 C23 1.552(8) . ? C22 C25 1.552(9) . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? C24 H24A 0.96 . ? C24 H24B 0.96 . ? C24 H24C 0.96 . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C23' H23D 0.96 . ? C23' H23E 0.96 . ? C23' H23F 0.96 . ? C24' H24D 0.96 . ? C24' H24E 0.96 . ? C24' H24F 0.96 . ? C25' H25D 0.96 . ? C25' H25E 0.96 . ? C25' H25F 0.96 . ? O1 C1 1.028(11) . ? O1 C1' 1.066(14) . ? O2 C2 1.029(12) . ? O3 C3 0.999(13) . ? 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 C21 Cu C21 111.0(2) . 2_655 ? C21 Cu C11 109.66(14) . . ? C21 Cu C11 108.32(14) 2_655 . ? C21 Cu C11 108.32(14) . 2_655 ? C21 Cu C11 109.66(14) 2_655 2_655 ? C11 Cu C11 109.9(2) . 2_655 ? N11 C11 Cu 177.7(3) . . ? C11 N11 C12 177.1(4) . . ? C15' C12 N11 114.0(12) . . ? C15 C12 N11 109.2(4) . . ? C15 C12 C13 117.5(4) . . ? N11 C12 C13 108.5(4) . . ? C15 C12 C14 107.7(5) . . ? N11 C12 C14 108.2(4) . . ? C13 C12 C14 105.4(4) . . ? C15' C12 C13' 131.9(13) . . ? N11 C12 C13' 106.4(8) . . ? C15' C12 C14' 95.3(14) . . ? N11 C12 C14' 103.4(9) . . ? C13' C12 C14' 99.8(12) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? C12 C13' H13D 109.5 . . ? C12 C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12 C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C12 C14' H14D 109.5 . . ? C12 C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C12 C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C12 C15' H15D 109.5 . . ? C12 C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C12 C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? N21 C21 Cu 178.6(3) . . ? C21 N21 C22 177.5(4) . . ? C24' C22 C23' 121.8(7) . . ? C24' C22 N21 113.6(5) . . ? C23' C22 N21 106.8(5) . . ? N21 C22 C24 107.5(4) . . ? C24' C22 C25' 110.4(7) . . ? C23' C22 C25' 95.6(6) . . ? N21 C22 C25' 106.4(5) . . ? N21 C22 C23 107.1(4) . . ? C24 C22 C23 113.6(5) . . ? N21 C22 C25 108.4(4) . . ? C24 C22 C25 113.2(5) . . ? C23 C22 C25 106.7(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? C22 C23' H23D 109.5 . . ? C22 C23' H23E 109.5 . . ? C22 C23' H23F 109.5 . . ? C22 C24' H24D 109.5 . . ? C22 C24' H24E 109.5 . . ? C22 C24' H24F 109.5 . . ? C22 C25' H25D 109.5 . . ? C22 C25' H25E 109.5 . . ? C22 C25' H25F 109.5 . . ? data_cubrtb _database_code_depnum_ccdc_archive 'CCDC 621968' _audit_creation_date 2006-08-24T20:12:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H38 Br Cu N4 O' _chemical_formula_moiety 'C20 H36 Cu N4, Br, H2 O' _chemical_formula_weight 493.99 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 32.570(2) _cell_length_b 15.4052(8) _cell_length_c 5.6365(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2828.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7340 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 24.6 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.199 _exptl_crystal_description bar _exptl_crystal_size_max .38 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .07 _exptl_crystal_size_rad ? _exptl_crystal_colour colourless _diffrn_measurement_device_type ; Bruker SMART CCD diffractometer ; _exptl_crystal_density_diffrn 1.16 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_absorpt_correction_T_min .61 _exptl_absorpt_correction_T_max .83 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents .079 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_number 51884 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 52 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 34.8 _diffrn_reflns_theta_full 34.8 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 6291 _reflns_number_gt 3840 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Siemens SMART (Siemens, 1995)' _computing_cell_refinement 'Siemens SAINT (Siemens, 1995)' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_molecular_graphics xtal _computing_publication_material WinGX _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0539P)^2^+7.9057P] 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_number_reflns 6291 _refine_ls_number_parameters 150 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1107 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.171 _refine_ls_wR_factor_gt 0.1599 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.306 _refine_diff_density_min -1.848 _refine_diff_density_rms 0.116 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cu Cu 0.133041(17) 0.25 0.69794(10) 0.01943(12) Uani 1 2 d S . . C11 C 0.08267(14) 0.25 0.8908(8) 0.0252(10) Uani 1 2 d S . . N11 N 0.05215(13) 0.25 0.9935(8) 0.0312(10) Uani 1 2 d S . . C12 C 0.01311(15) 0.25 1.1226(9) 0.0349(13) Uani 1 2 d S . . C13 C -0.01031(13) 0.3308(3) 1.0525(9) 0.0483(11) Uani 1 1 d . . . H13A H 0.0055 0.3823 1.0977 0.072 Uiso 1 1 calc R . . H13B H -0.0369 0.3315 1.1339 0.072 Uiso 1 1 calc R . . H13C H -0.0147 0.3308 0.8805 0.072 Uiso 1 1 calc R . . C14 C 0.0244(2) 0.25 1.3849(11) 0.067(3) Uani 1 2 d SD . . C21 C 0.13254(11) 0.1461(2) 0.4973(6) 0.0268(6) Uani 1 1 d . . . N21 N 0.13151(11) 0.0839(2) 0.3860(6) 0.0328(7) Uani 1 1 d . . . C22 C 0.13097(15) 0.0016(2) 0.2545(7) 0.0383(9) Uani 1 1 d . . . C23 C 0.1404(3) -0.0687(3) 0.4216(10) 0.097(3) Uani 1 1 d . . . H23A H 0.1656 -0.0546 0.5087 0.145 Uiso 1 1 calc R . . H23B H 0.1443 -0.123 0.3339 0.145 Uiso 1 1 calc R . . H23C H 0.1176 -0.0754 0.5337 0.145 Uiso 1 1 calc R . . C24 C 0.09230(15) -0.0042(4) 0.1188(9) 0.109(3) Uani 1 1 d . . . H24A H 0.069 -0.0056 0.2289 0.163 Uiso 1 1 calc R . . H24B H 0.0924 -0.0572 0.0228 0.163 Uiso 1 1 calc R . . H24C H 0.0898 0.0465 0.0146 0.163 Uiso 1 1 calc R . . C25 C 0.16636(15) 0.0042(4) 0.0708(9) 0.082(2) Uani 1 1 d . . . H25A H 0.1633 0.0551 -0.0319 0.124 Uiso 1 1 d R . . H25B H 0.1653 -0.0486 -0.0259 0.124 Uiso 1 1 d R . . H25C H 0.1928 0.0072 0.1534 0.124 Uiso 1 1 d R . . C31 C 0.18197(16) 0.25 0.9010(9) 0.0262(10) Uani 1 2 d S . . N31 N 0.21126(13) 0.25 1.0107(8) 0.0319(10) Uani 1 2 d S . . C32 C 0.25066(15) 0.25 1.1372(10) 0.0334(12) Uani 1 2 d S . . C33 C 0.25267(14) 0.1695(3) 1.2893(9) 0.0524(13) Uani 1 1 d . . . H33A H 0.2298 0.1697 1.4023 0.079 Uiso 1 1 calc R . . H33B H 0.2787 0.1685 1.3761 0.079 Uiso 1 1 calc R . . H33C H 0.2508 0.1179 1.1881 0.079 Uiso 1 1 calc R . . C34 C 0.28417(18) 0.25 0.9498(11) 0.0509(18) Uani 1 2 d SD . . Br Br 0.368825(16) 0.25 1.42965(8) 0.02745(12) Uani 1 2 d S . . O1 O 0.42701(13) 0.25 0.9286(8) 0.0656(17) Uani 1 2 d S . . H14A H 0.0405 0.19807 1.423 0.098 Uiso 1 1 d D . . H14B H -0.0009 0.25 1.479 0.098 Uiso 1 2 d SD . . H34A H 0.2831 0.30193 0.8496 0.098 Uiso 1 1 d D . . H34B H 0.3098 0.25 1.041 0.098 Uiso 1 2 d SD . . 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 Cu 0.0168(2) 0.0192(2) 0.0223(3) 0 -0.0015(2) 0 C11 0.0157(19) 0.037(3) 0.023(2) 0 0.0003(16) 0 N11 0.0215(19) 0.051(3) 0.0211(19) 0 -0.0037(15) 0 C12 0.0153(19) 0.065(4) 0.024(2) 0 0.0029(17) 0 C13 0.0265(18) 0.059(3) 0.060(3) -0.008(2) 0.0109(19) 0.0035(19) C14 0.026(3) 0.152(9) 0.022(3) 0 0.003(2) 0 C21 0.0290(15) 0.0241(14) 0.0273(14) 0.0005(12) -0.0002(14) -0.0001(14) N21 0.0430(17) 0.0225(13) 0.0330(15) -0.0032(12) -0.0056(14) 0.0016(14) C22 0.061(3) 0.0190(14) 0.0346(17) -0.0088(14) -0.014(2) 0.0028(17) C23 0.220(10) 0.026(2) 0.045(3) -0.005(2) -0.026(4) 0.017(4) C24 0.071(4) 0.079(5) 0.177(8) -0.080(5) -0.063(5) 0.024(3) C25 0.105(5) 0.059(4) 0.082(5) -0.039(3) 0.035(4) -0.019(4) C31 0.029(2) 0.027(2) 0.022(2) 0 -0.0025(18) 0 N31 0.023(2) 0.046(3) 0.027(2) 0 -0.0062(17) 0 C32 0.021(2) 0.053(3) 0.027(2) 0 -0.0054(19) 0 C33 0.040(2) 0.065(3) 0.052(3) 0.020(3) -0.015(2) -0.004(2) C34 0.024(3) 0.100(6) 0.028(3) 0 -0.001(2) 0 Br 0.0279(2) 0.0324(3) 0.0221(2) 0 -0.0048(2) 0 O1 0.0212(19) 0.141(5) 0.035(2) 0 0.0007(18) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu C21 1.960(3) . ? Cu C21 1.960(3) 8_565 ? Cu C31 1.962(5) . ? Cu C11 1.968(5) . ? C11 N11 1.150(6) . ? N11 C12 1.465(6) . ? C12 C13 1.512(6) 8_565 ? C12 C13 1.512(6) . ? C12 C14 1.523(8) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.980 . ? C14 H14B 0.980 . ? C21 N21 1.146(5) . ? N21 C22 1.468(4) . ? C22 C23 1.468(6) . ? C22 C24 1.476(6) . ? C22 C25 1.550(7) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? C25 H25A 0.9807 . ? C25 H25B 0.9793 . ? C25 H25C 0.98 . ? C31 N31 1.137(6) . ? N31 C32 1.468(6) . ? C32 C33 1.509(5) 8_565 ? C32 C33 1.509(5) . ? C32 C34 1.519(8) . ? C33 H33A 0.98 . ? C33 H33B 0.98 . ? C33 H33C 0.98 . ? C34 H34A 0.980 . ? C34 H34B 0.980 . ? 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 C21 Cu C21 109.5(2) . 8_565 ? C21 Cu C31 110.08(13) . . ? C21 Cu C31 110.08(13) 8_565 . ? C21 Cu C11 108.18(13) . . ? C21 Cu C11 108.18(13) 8_565 . ? C31 Cu C11 110.8(2) . . ? N11 C11 Cu 176.7(4) . . ? C11 N11 C12 179.6(5) . . ? N11 C12 C13 107.9(3) . 8_565 ? N11 C12 C13 107.9(3) . . ? C13 C12 C13 110.8(5) 8_565 . ? N11 C12 C14 105.9(4) . . ? C13 C12 C14 112.0(3) 8_565 . ? C13 C12 C14 112.0(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 110 . . ? C12 C14 H14B 109 . . ? H14A C14 H14B 109.4 . . ? N21 C21 Cu 177.6(3) . . ? C21 N21 C22 177.0(4) . . ? C23 C22 N21 108.1(3) . . ? C23 C22 C24 117.8(5) . . ? N21 C22 C24 108.9(4) . . ? C23 C22 C25 107.0(5) . . ? N21 C22 C25 107.9(4) . . ? C24 C22 C25 106.9(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.7 . . ? C22 C25 H25B 109 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.7 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N31 C31 Cu 177.3(5) . . ? C31 N31 C32 176.1(5) . . ? N31 C32 C33 108.3(3) . 8_565 ? N31 C32 C33 108.3(3) . . ? C33 C32 C33 110.6(5) 8_565 . ? N31 C32 C34 106.9(5) . . ? C33 C32 C34 111.3(3) 8_565 . ? C33 C32 C34 111.3(3) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 112 . . ? C32 C34 H34B 104 . . ? H34A C34 H34B 109.5 . . ? #===END # Attachment 'cuitb.cif' data_cuitb _database_code_depnum_ccdc_archive 'CCDC 621969' _audit_creation_date 2006-08-24T13:40:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H36 Cu I N4' _chemical_formula_moiety 'C20 H36 Cu N4, I' _chemical_formula_weight 522.97 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I-4m2 _symmetry_space_group_name_Hall i_-4_-2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z' '-x, -y, z' 'x, -y, z' 'y, x, -z' '-y, x, -z' 'y, -x, -z' '-y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' 'y+1/2, x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' _cell_length_a 15.5780(10) _cell_length_b 15.5780(10) _cell_length_c 17.631(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4278.6(6) _cell_formula_units_Z 6 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5848 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description pyramid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1596 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.857 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.67 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker SMART CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_unetI/netI 0.0135 _diffrn_reflns_number 32087 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 33.95 _diffrn_reflns_theta_full 33.95 _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.964 _reflns_number_total 4413 _reflns_number_gt 3416 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Siemens SMART (Siemens, 1995)' _computing_cell_refinement 'Siemens SAINT (Siemens, 1995)' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0378P)^2^+0.3343P] 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_expression 'Eq22 p292 "Cryst. Comp." Munksgaard 1970' _refine_ls_extinction_coef 43E2(4) _refine_ls_number_reflns 4413 _refine_ls_number_parameters 127 _refine_ls_number_restraints 15 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.066 _refine_ls_wR_factor_gt 0.059 _refine_ls_wR_factor_all 0.032 _refine_ls_goodness_of_fit_all 1.269 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_diff_density_max 0.31 _refine_diff_density_min -1.585 _refine_diff_density_rms 0.108 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5 0 0.40702(2) 0.02238(8) Uani 1 4 d S . . C111 C 0.5 0.10349(15) 0.34472(13) 0.0325(5) Uani 1 2 d S . . N111 N 0.5 0.16705(14) 0.31137(11) 0.0355(4) Uani 1 2 d S . . C112 C 0.5 0.25060(18) 0.27293(13) 0.0324(5) Uani 1 2 d S . . C113 C 0.5 0.31897(16) 0.33537(19) 0.0480(7) Uani 1 2 d SD . . C114 C 0.58030(15) 0.25524(11) 0.22438(11) 0.0446(5) Uani 1 1 d . . . H11D H 0.6312 0.252 0.257 0.067 Uiso 1 1 calc R . . H11E H 0.5808 0.3095 0.1963 0.067 Uiso 1 1 calc R . . H11F H 0.5808 0.2071 0.1885 0.067 Uiso 1 1 calc R . . C121 C 0.39559(14) 0 0.46965(14) 0.0303(5) Uani 1 2 d S . . N121 N 0.33294(12) 0 0.50350(14) 0.0330(4) Uani 1 2 d S . . C122 C 0.2529(2) 0 0.54714(15) 0.0337(5) Uani 1 2 d S . . C123 C 0.25258(13) -0.08081(17) 0.59615(13) 0.0679(8) Uani 1 1 d . . . H12A H 0.3008 -0.0787 0.6318 0.102 Uiso 1 1 calc R . . H12B H 0.2582 -0.1315 0.5636 0.102 Uiso 1 1 calc R . . H12C H 0.1985 -0.0841 0.6244 0.102 Uiso 1 1 calc R . . C124 C 0.17976(16) 0 0.49168(19) 0.0484(7) Uani 1 2 d SD . . Cu2 Cu 0.5 0.5 0.5 0.02402(13) Uani 1 8 d S . . C211 C 0.5 0.39645(16) 0.56125(13) 0.0308(5) Uani 1 2 d S . . N211 N 0.5 0.33239(14) 0.59424(12) 0.0324(4) Uani 1 2 d S . . C212 C 0.5 0.25040(13) 0.63450(14) 0.0313(7) Uani 1 2 d S . . C213 C 0.5 0.17912(17) 0.57590(19) 0.0470(7) Uani 1 2 d SD . . C214 C 0.42038(16) 0.24821(11) 0.68383(11) 0.0496(5) Uani 1 1 d . . . H21D H 0.4229 0.295 0.7209 0.074 Uiso 1 1 calc R . . H21E H 0.4175 0.1931 0.7105 0.074 Uiso 1 1 calc R . . H21F H 0.3693 0.2551 0.652 0.074 Uiso 1 1 calc R . . I1 I 0.5 0.5 0.171518(13) 0.03056(6) Uani 1 4 d S . . I2 I 0.5 0 0.75 0.03419(9) Uani 1 8 d S . . H11A H 0.5 0.3762 0.3113 0.051 Uiso 1 2 d SD . . H11B H 0.4485 0.3142 0.3668 0.051 Uiso 1 1 d D . . H12D H 0.1233 0 0.5153 0.051 Uiso 1 2 d SD . . H12E H 0.1869 0.0516 0.4602 0.051 Uiso 1 1 d D . . H21A H 0.4483 0.1861 0.5454 0.051 Uiso 1 1 d D . . H21B H 0.5 0.1215 0.5984 0.051 Uiso 1 2 d SD . . 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 0.0233(2) 0.0181(2) 0.02575(17) 0 0 0 C111 0.0371(12) 0.0263(11) 0.0342(12) -0.0003(9) 0 0 N111 0.0457(11) 0.0240(9) 0.0367(10) 0.0028(8) 0 0 C112 0.0439(14) 0.0186(12) 0.0347(11) 0.0025(9) 0 0 C113 0.0770(19) 0.0281(13) 0.0389(12) -0.0024(14) 0 0 C114 0.0469(12) 0.0329(10) 0.0540(10) 0.0075(8) 0.0111(9) 0.0045(8) C121 0.0268(10) 0.0315(12) 0.0326(10) 0 -0.0036(8) 0 N121 0.0264(9) 0.0412(11) 0.0315(8) 0 0.0009(9) 0 C122 0.0227(10) 0.0487(15) 0.0298(10) 0 0.0024(9) 0 C123 0.0521(14) 0.084(2) 0.0674(15) 0.0385(14) 0.0192(12) 0.0148(12) C124 0.0272(12) 0.080(2) 0.0380(16) 0 -0.0018(12) 0 Cu2 0.02237(19) 0.02237(19) 0.0273(2) 0 0 0 C211 0.0329(12) 0.0288(12) 0.0308(11) -0.0045(9) 0 0 N211 0.0401(11) 0.0278(10) 0.0293(9) -0.0007(8) 0 0 C212 0.0392(19) 0.0236(15) 0.0311(10) 0.0017(10) 0 0 C213 0.073(2) 0.0283(13) 0.0394(14) 0.0007(14) 0 0 C214 0.0582(14) 0.0403(11) 0.0504(12) 0.0107(9) 0.0131(11) 0.0020(9) I1 0.03617(16) 0.02272(12) 0.03279(10) 0 0 0 I2 0.02981(13) 0.02981(13) 0.04294(18) 0 0 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C111 1.951(2) 3_655 ? Cu1 C111 1.951(2) . ? Cu1 C121 1.966(2) 2_655 ? Cu1 C121 1.966(2) . ? C111 N111 1.152(3) . ? N111 C112 1.467(3) . ? C112 C114 1.517(2) 2_655 ? C112 C114 1.517(2) . ? C112 C113 1.532(4) . ? C113 H11A 0.987 . ? C113 H11B 0.978 . ? C114 H11D 0.98 . ? C114 H11E 0.98 . ? C114 H11F 0.98 . ? C121 N121 1.144(3) . ? N121 C122 1.466(4) . ? C122 C124 1.501(4) . ? C122 C123 1.527(3) . ? C122 C123 1.527(3) 4 ? C123 H12A 0.98 . ? C123 H12B 0.98 . ? C123 H12C 0.98 . ? C124 H12D 0.973 . ? C124 H12E 0.983 . ? Cu2 C211 1.941(2) 5_556 ? Cu2 C211 1.941(2) 6_656 ? Cu2 C211 1.941(2) . ? Cu2 C211 1.941(2) 3_665 ? C211 N211 1.155(3) . ? N211 C212 1.461(3) . ? C212 C214 1.515(2) . ? C212 C214 1.515(2) 2_655 ? C212 C213 1.517(4) . ? C213 H21A 0.974 . ? C213 H21B 0.981 . ? C214 H21D 0.98 . ? C214 H21E 0.98 . ? C214 H21F 0.98 . ? 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 C111 Cu1 C111 111.47(14) 3_655 . ? C111 Cu1 C121 108.44(5) 3_655 2_655 ? C111 Cu1 C121 108.44(5) . 2_655 ? C111 Cu1 C121 108.44(5) 3_655 . ? C111 Cu1 C121 108.44(5) . . ? C121 Cu1 C121 111.65(14) 2_655 . ? N111 C111 Cu1 176.4(2) . . ? C111 N111 C112 176.8(2) . . ? N111 C112 C114 107.62(15) . 2_655 ? N111 C112 C114 107.62(15) . . ? C114 C112 C114 111.1(2) 2_655 . ? N111 C112 C113 106.5(2) . . ? C114 C112 C113 111.86(15) 2_655 . ? C114 C112 C113 111.86(15) . . ? C112 C113 H11A 108.6 . . ? C112 C113 H11B 110.8 . . ? H11A C113 H11B 108.2 . . ? C112 C114 H11D 109.5 . . ? C112 C114 H11E 109.5 . . ? H11D C114 H11E 109.5 . . ? C112 C114 H11F 109.5 . . ? H11D C114 H11F 109.5 . . ? H11E C114 H11F 109.5 . . ? N121 C121 Cu1 177.3(2) . . ? C121 N121 C122 179.8(3) . . ? N121 C122 C124 107.7(2) . . ? N121 C122 C123 107.43(18) . . ? C124 C122 C123 111.50(18) . . ? N121 C122 C123 107.43(18) . 4 ? C124 C122 C123 111.50(18) . 4 ? C123 C122 C123 111.1(3) . 4 ? C122 C123 H12A 109.5 . . ? C122 C123 H12B 109.5 . . ? H12A C123 H12B 109.5 . . ? C122 C123 H12C 109.5 . . ? H12A C123 H12C 109.5 . . ? H12B C123 H12C 109.5 . . ? C122 C124 H12D 114.0 . . ? C122 C124 H12E 106.4 . . ? H12D C124 H12E 110.2 . . ? C211 Cu2 C211 112.40(14) 5_556 6_656 ? C211 Cu2 C211 108.03(7) 5_556 . ? C211 Cu2 C211 108.03(7) 6_656 . ? C211 Cu2 C211 108.03(7) 5_556 3_665 ? C211 Cu2 C211 108.03(7) 6_656 3_665 ? C211 Cu2 C211 112.40(14) . 3_665 ? N211 C211 Cu2 176.4(2) . . ? C211 N211 C212 178.8(2) . . ? N211 C212 C214 107.37(12) . . ? N211 C212 C214 107.37(12) . 2_655 ? C214 C212 C214 109.9(2) . 2_655 ? N211 C212 C213 108.0(2) . . ? C214 C212 C213 111.99(13) . . ? C214 C212 C213 111.99(13) 2_655 . ? C212 C213 H21A 107.1 . . ? C212 C213 H21B 113.2 . . ? H21A C213 H21B 109.0 . . ? C212 C214 H21D 109.5 . . ? C212 C214 H21E 109.5 . . ? H21D C214 H21E 109.5 . . ? C212 C214 H21F 109.5 . . ? H21D C214 H21F 109.5 . . ? H21E C214 H21F 109.5 . . ? #===END # Attachment 'cuctbx.cif' data_cuctbx _database_code_depnum_ccdc_archive 'CCDC 621970' _audit_creation_date 2006-10-26T10:26:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C10 H18 Cl Cu N2' _chemical_formula_moiety 'C10 H18 Cl Cu N2' _chemical_formula_weight 265.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -c_2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.912(7) _cell_length_b 9.861(4) _cell_length_c 18.609(6) _cell_angle_alpha 90 _cell_angle_beta 116.64(3) _cell_angle_gamma 90 _cell_volume 2774.0(20) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 9.4 _cell_measurement_theta_max 11.6 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_absorpt_coefficient_mu 1.738 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min .86 _exptl_absorpt_correction_T_max .98 _exptl_absorpt_process_details ; XTAL absorb ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; CAD4 diffractometer ; _diffrn_measurement_method '2\q-\w scans' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.1737 _diffrn_reflns_number 2326 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.945 _diffrn_standards_number 6 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _reflns_number_total 2326 _reflns_number_gt 1267 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Enraf Nonius software' _computing_cell_refinement 'Enraf Nonius software' _computing_data_reduction 'xtal ADDREF SORTRF' _computing_structure_solution xtal _computing_molecular_graphics xtal _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material Shelx #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0200P)^2^+245.0000P] 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_number_reflns 2326 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.145 _refine_ls_R_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.2729 _refine_ls_wR_factor_gt 0.2117 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.004 _refine_diff_density_max 0.352 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.09 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.36864(10) 0.13701(17) 0.49882(9) 0.0618(5) Uani 1 1 d . . . Cl1 Cl 0.2727(3) 0.0010(4) 0.4046(2) 0.0809(11) Uani 1 1 d . . . C1 C 0.3538(9) 0.1451(15) 0.5944(8) 0.069(3) Uani 1 1 d . . . N1 N 0.3474(7) 0.1416(11) 0.6527(6) 0.063(3) Uani 1 1 d . . . C11 C 0.3375(8) 0.1322(13) 0.7270(6) 0.059(3) Uani 1 1 d . . . C12 C 0.3849(11) 0.2519(19) 0.7782(9) 0.107(6) Uani 1 1 d . . . H12A H 0.4468 0.2461 0.7925 0.161 Uiso 1 1 calc R . . H12B H 0.3769 0.2521 0.8261 0.161 Uiso 1 1 calc R . . H12C H 0.3611 0.3341 0.7487 0.161 Uiso 1 1 calc R . . C13 C 0.3796(13) 0.0023(18) 0.7663(11) 0.113(7) Uani 1 1 d . . . H13A H 0.3507 -0.0719 0.7307 0.17 Uiso 1 1 calc R . . H13B H 0.3742 -0.0085 0.8151 0.17 Uiso 1 1 calc R . . H13C H 0.4411 0.0035 0.7783 0.17 Uiso 1 1 calc R . . C14 C 0.2410(9) 0.1368(19) 0.7040(8) 0.092(5) Uani 1 1 d . . . H14A H 0.2162 0.2193 0.6754 0.138 Uiso 1 1 calc R . . H14B H 0.2325 0.1335 0.7517 0.138 Uiso 1 1 calc R . . H14C H 0.2122 0.0605 0.6704 0.138 Uiso 1 1 calc R . . C2 C 0.4532(8) 0.2200(14) 0.4724(7) 0.063(3) Uani 1 1 d . . . N2 N 0.5031(7) 0.2726(10) 0.4547(6) 0.060(3) Uani 1 1 d . . . C21 C 0.5685(7) 0.3397(12) 0.4335(7) 0.053(3) Uani 1 1 d . . . C22 C 0.5212(11) 0.4508(18) 0.3783(12) 0.112(6) Uani 1 1 d . . . H22A H 0.4731 0.4145 0.3311 0.168 Uiso 1 1 calc R . . H22B H 0.5611 0.4982 0.3633 0.168 Uiso 1 1 calc R . . H22C H 0.4985 0.5124 0.4045 0.168 Uiso 1 1 calc R . . C23 C 0.6015(9) 0.2314(15) 0.3951(9) 0.084(5) Uani 1 1 d . . . H23A H 0.6294 0.1598 0.4331 0.126 Uiso 1 1 calc R . . H23B H 0.6434 0.2707 0.3795 0.126 Uiso 1 1 calc R . . H23C H 0.5524 0.1953 0.3485 0.126 Uiso 1 1 calc R . . C24 C 0.6421(9) 0.3851(18) 0.5123(8) 0.091(5) Uani 1 1 d . . . H24A H 0.6185 0.443 0.5394 0.136 Uiso 1 1 calc R . . H24B H 0.6854 0.4339 0.5025 0.136 Uiso 1 1 calc R . . H24C H 0.6692 0.3072 0.5451 0.136 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0688(10) 0.0743(10) 0.0553(9) 0.0005(8) 0.0393(7) -0.0115(8) Cl1 0.096(3) 0.095(3) 0.068(2) -0.0176(18) 0.0510(19) -0.037(2) C1 0.067(8) 0.080(9) 0.076(8) 0.001(7) 0.046(7) -0.015(7) N1 0.070(7) 0.069(7) 0.062(6) -0.009(5) 0.041(5) -0.011(5) C11 0.062(7) 0.078(8) 0.045(6) -0.005(6) 0.032(5) -0.006(7) C12 0.100(12) 0.150(17) 0.087(10) -0.068(11) 0.056(9) -0.059(12) C13 0.149(17) 0.122(14) 0.123(14) 0.050(12) 0.109(14) 0.049(13) C14 0.066(9) 0.148(15) 0.064(8) 0.025(9) 0.032(7) -0.007(10) C2 0.070(8) 0.071(8) 0.055(7) -0.007(6) 0.035(6) -0.014(7) N2 0.067(6) 0.062(6) 0.062(6) -0.006(5) 0.039(5) -0.011(5) C21 0.053(6) 0.063(7) 0.055(6) 0.002(5) 0.036(6) -0.004(6) C22 0.100(12) 0.115(14) 0.152(17) 0.062(13) 0.084(12) 0.031(11) C23 0.082(10) 0.089(10) 0.104(11) -0.048(9) 0.062(9) -0.025(8) C24 0.066(9) 0.146(16) 0.072(9) -0.012(9) 0.041(7) -0.035(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.894(12) . ? Cu1 C1 1.906(13) . ? Cu1 Cl1 2.226(4) . ? C1 N1 1.137(14) . ? N1 C11 1.468(13) . ? C11 C14 1.491(17) . ? C11 C13 1.489(19) . ? C11 C12 1.503(18) . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C2 N2 1.157(14) . ? N2 C21 1.487(14) . ? C21 C22 1.469(18) . ? C21 C24 1.503(16) . ? C21 C23 1.523(16) . ? C22 H22A 0.96 . ? C22 H22B 0.96 . ? C22 H22C 0.96 . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? C24 H24A 0.96 . ? C24 H24B 0.96 . ? C24 H24C 0.96 . ? 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 Cu1 C1 130.9(5) . . ? C2 Cu1 Cl1 115.1(4) . . ? C1 Cu1 Cl1 113.9(4) . . ? N1 C1 Cu1 175.5(13) . . ? C1 N1 C11 177.8(13) . . ? N1 C11 C14 107.5(10) . . ? N1 C11 C13 106.6(10) . . ? C14 C11 C13 112.8(13) . . ? N1 C11 C12 107.1(10) . . ? C14 C11 C12 111.2(13) . . ? C13 C11 C12 111.3(13) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C2 Cu1 178.1(12) . . ? C2 N2 C21 178.9(13) . . ? C22 C21 N2 106.3(10) . . ? C22 C21 C24 114.4(13) . . ? N2 C21 C24 105.2(9) . . ? C22 C21 C23 113.2(12) . . ? N2 C21 C23 106.6(10) . . ? C24 C21 C23 110.4(11) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? #===END # Attachment 'cutbbr.cif' data_cutbbr _database_code_depnum_ccdc_archive 'CCDC 637950' _audit_creation_date 2007-02-23T12:01:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C20 H36 Br Cu N4' _chemical_formula_moiety 'C20 H36 Cu N4, Br' _chemical_formula_weight 475.98 _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M i-4m2 _symmetry_space_group_name_Hall I_-4_-2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, -x, -z' 'y, x, -z' '-x, y, z' 'x, -y, z' '-y, x, -z' 'y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, -x+1/2, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' _cell_length_a 15.2887(5) _cell_length_b 15.2887(5) _cell_length_c 5.6096(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1311.21(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1305 _cell_measurement_theta_min 2.6578 _cell_measurement_theta_max 28.5704 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.044 _exptl_crystal_size_min 0.042 _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.9105 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.0178101299 _diffrn_orient_matrix_ub_12 -0.0387764992 _diffrn_orient_matrix_ub_13 0.0500725869 _diffrn_orient_matrix_ub_21 0.042135291 _diffrn_orient_matrix_ub_22 0.0121122739 _diffrn_orient_matrix_ub_23 -0.0417432811 _diffrn_orient_matrix_ub_31 0.0080908607 _diffrn_orient_matrix_ub_32 0.0224909103 _diffrn_orient_matrix_ub_33 0.1083332404 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_unetI/netI 0.1068 _diffrn_reflns_number 3596 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 28.78 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer ; _diffrn_measurement_method '\p and \w scans' _reflns_number_total 840 _reflns_number_gt 608 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0120P)^2^] 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_number_reflns 840 _refine_ls_number_parameters 44 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0457 _refine_ls_wR_factor_gt 0.044 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.94 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.018(17) _refine_diff_density_max 0.722 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.071 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cu Cu 0.5 0.5 0.5 0.0168(4) Uani 1 8 d S . . Br Br 1 0.5 0.75 0.0197(3) Uani 1 8 d S . . C1 C 0.3948(2) 0.5 0.3035(7) 0.0183(10) Uani 1 2 d S . . C3 C 0.1749(2) 0.5 0.2510(11) 0.0306(10) Uani 1 2 d SD . . H3A H 0.1818 0.5510 0.349 0.046 Uiso 1 1 d D . . H3B H 0.1176 0.5 0.181 0.046 Uiso 1 2 d SD . . N1 N 0.33110(19) 0.5 0.1952(6) 0.0200(8) Uani 1 2 d S . . C2 C 0.2476(3) 0.5 0.0665(7) 0.0224(14) Uani 1 2 d S . . C4 C 0.24262(17) 0.41787(17) -0.0876(5) 0.0324(8) Uani 1 1 d . . . H4A H 0.2909 0.418 -0.2026 0.049 Uiso 1 1 calc R . . H4B H 0.1867 0.4169 -0.1732 0.049 Uiso 1 1 calc R . . H4C H 0.2471 0.3659 0.0141 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0156(5) 0.0156(5) 0.0191(10) 0 0 0 Br 0.0203(4) 0.0203(4) 0.0185(8) 0 0 0 C1 0.018(2) 0.0159(19) 0.021(3) 0 0.0066(19) 0 C3 0.0120(19) 0.048(3) 0.032(3) 0 -0.004(3) 0 N1 0.0191(19) 0.0250(19) 0.016(2) 0 0.0006(17) 0 C2 0.0164(19) 0.0215(19) 0.029(4) 0 -0.003(3) 0 C4 0.0220(17) 0.0395(19) 0.036(2) -0.0115(16) -0.0094(15) 0.0047(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu C1 1.950(4) 4_556 ? Cu C1 1.950(4) . ? Cu C1 1.950(4) 2_665 ? Cu C1 1.950(4) 3_666 ? C1 N1 1.148(4) . ? C3 C2 1.519(6) . ? C3 H3A 0.960 . ? C3 H3B 0.960 . ? N1 C2 1.466(5) . ? C2 C4 1.526(3) . ? C2 C4 1.526(3) 6_565 ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu C1 108.64(11) 4_556 . ? C1 Cu C1 108.64(11) 4_556 2_665 ? C1 Cu C1 111.1(2) . 2_665 ? C1 Cu C1 111.1(2) 4_556 3_666 ? C1 Cu C1 108.64(11) . 3_666 ? C1 Cu C1 108.64(11) 2_665 3_666 ? N1 C1 Cu 177.5(3) . . ? C2 C3 H3A 108.1 . . ? C2 C3 H3B 113 . . ? H3A C3 H3B 109.48 . . ? C1 N1 C2 177.5(4) . . ? N1 C2 C3 107.5(3) . . ? N1 C2 C4 108.8(3) . . ? C3 C2 C4 110.4(3) . . ? N1 C2 C4 108.8(3) . 6_565 ? C3 C2 C4 110.4(3) . 6_565 ? C4 C2 C4 110.7(3) . 6_565 ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? #===END # Attachment 'gban22.cif' data_gban22 _database_code_depnum_ccdc_archive 'CCDC 656851' _audit_creation_date 2007-08-04T21:46:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C6 H9 Cu N2' _chemical_formula_moiety 'C6 H9 Cu N2' _chemical_formula_weight 172.69 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 20.0645(9) _cell_length_b 20.0645(9) _cell_length_c 10.2064(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 3558.4(3) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1584 _cell_measurement_theta_min 3.0561 _cell_measurement_theta_max 28.2359 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description hexagonal_plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.678 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.98101 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 -0.0385566827 _diffrn_orient_matrix_ub_12 -0.0153340919 _diffrn_orient_matrix_ub_13 0.0214879308 _diffrn_orient_matrix_ub_21 -0.0082677592 _diffrn_orient_matrix_ub_22 -0.0373103867 _diffrn_orient_matrix_ub_23 -0.0194752293 _diffrn_orient_matrix_ub_31 0.0106223855 _diffrn_orient_matrix_ub_32 -0.0062266916 _diffrn_orient_matrix_ub_33 0.0631434567 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_unetI/netI 0.1875 _diffrn_reflns_number 10525 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.942 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer ; _diffrn_measurement_method '\p and \w scans' _reflns_number_total 1848 _reflns_number_gt 882 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0211P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1848 _refine_ls_number_parameters 85 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1469 _refine_ls_R_factor_gt 0.046 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_restrained_S_all 0.855 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.57 _refine_diff_density_min -0.39 _refine_diff_density_rms 0.105 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 Cu Cu 0.45352(3) 0.40950(3) 0.09194(6) 0.02560(18) Uani 1 1 d . . . N1 N 0.3969(2) 0.3295(2) -0.0352(4) 0.0199(10) Uani 0.5 1 d P . . C1 C 0.3969(2) 0.3295(2) -0.0352(4) 0.0199(10) Uani 0.5 1 d P . . C2 C 0.3579(2) 0.2826(2) -0.1112(4) 0.0246(10) Uani 0.5 1 d P . . N2 N 0.3579(2) 0.2826(2) -0.1112(4) 0.0246(10) Uani 0.5 1 d P . . C11 C 0.5613(3) 0.4650(3) 0.0920(4) 0.0271(12) Uani 1 1 d . . . N11 N 0.6276(2) 0.4931(2) 0.0924(4) 0.0260(10) Uani 1 1 d . . . C12 C 0.7112(2) 0.5261(3) 0.0827(4) 0.0230(11) Uani 1 1 d . . . C13 C 0.7471(2) 0.6115(2) 0.0558(4) 0.0293(12) Uani 1 1 d . . . H13A H 0.7262 0.6191 -0.026 0.044 Uiso 1 1 calc R . . H13B H 0.803 0.6346 0.0478 0.044 Uiso 1 1 calc R . . H13C H 0.7352 0.6359 0.1282 0.044 Uiso 1 1 calc R . . C14 C 0.7385(3) 0.5113(3) 0.2126(5) 0.0455(15) Uani 1 1 d . . . H14A H 0.7264 0.5367 0.2831 0.068 Uiso 1 1 calc R . . H14B H 0.7942 0.5319 0.2092 0.068 Uiso 1 1 calc R . . H14C H 0.7124 0.4558 0.2292 0.068 Uiso 1 1 calc R . . C15 C 0.7247(3) 0.4852(3) -0.0320(5) 0.0440(15) Uani 1 1 d . . . H15A H 0.6972 0.4296 -0.016 0.066 Uiso 1 1 calc R . . H15B H 0.7799 0.5039 -0.0407 0.066 Uiso 1 1 calc R . . H15C H 0.7055 0.4961 -0.113 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0183(3) 0.0272(4) 0.0297(3) -0.0051(3) -0.0007(3) 0.0102(3) N1 0.019(2) 0.024(3) 0.020(2) -0.001(2) -0.0006(19) 0.013(2) C1 0.019(2) 0.024(3) 0.020(2) -0.001(2) -0.0006(19) 0.013(2) C2 0.028(3) 0.021(2) 0.028(3) 0.007(2) -0.001(2) 0.015(2) N2 0.028(3) 0.021(2) 0.028(3) 0.007(2) -0.001(2) 0.015(2) C11 0.032(3) 0.029(3) 0.022(3) -0.005(2) -0.002(2) 0.017(3) N11 0.015(2) 0.033(2) 0.030(3) 0.0007(19) 0.0040(19) 0.012(2) C12 0.014(3) 0.030(3) 0.024(3) -0.002(2) 0.000(2) 0.010(2) C13 0.018(3) 0.033(3) 0.035(3) -0.003(3) -0.003(2) 0.012(2) C14 0.026(3) 0.053(4) 0.052(4) 0.016(3) -0.005(3) 0.015(3) C15 0.023(3) 0.039(3) 0.064(4) -0.020(3) 0.004(3) 0.011(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu C11 1.873(5) . ? Cu N2 1.919(5) 5 ? Cu C2 1.919(5) 5 ? Cu N1 1.931(4) . ? N1 C2 1.168(5) . ? C2 Cu 1.919(5) 9_554 ? C11 N11 1.157(5) . ? N11 C12 1.467(5) . ? C12 C13 1.515(6) . ? C12 C14 1.518(6) . ? C12 C15 1.528(6) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? 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 C11 Cu N2 128.44(17) . 5 ? C11 Cu C2 128.44(17) . 5 ? C11 Cu N1 121.32(17) . . ? N2 Cu N1 109.59(15) 5 . ? C2 Cu N1 109.59(15) 5 . ? C2 N1 Cu 174.6(4) . . ? N1 C2 Cu 173.2(4) . 9_554 ? N11 C11 Cu 173.9(4) . . ? C11 N11 C12 175.5(5) . . ? N11 C12 C13 108.1(3) . . ? N11 C12 C14 107.2(4) . . ? C13 C12 C14 111.4(4) . . ? N11 C12 C15 106.2(4) . . ? C13 C12 C15 110.9(4) . . ? C14 C12 C15 112.8(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? #===END