# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _publ_contact_author_name 'Ribas, Xavi' _publ_contact_author_email xavi.ribas@udg.edu _publ_section_title ; Direct Observation of CuI/CuIII Redox Steps Relevant to Ullmann-Type Coupling Reactions ; loop_ _publ_author_name A.Casitas A.King T.Parella M.Costas S.Stahl X.Ribas # Attachment '- 1Cl_acml1p57pca21_last.cif' data_acml1p57pca21 _database_code_depnum_ccdc_archive 'CCDC 735508' #TrackingRef '- 1Cl_acml1p57pca21_last.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 Cl Cu N3, Cl' _chemical_formula_sum 'C15 H24 Cl2 Cu N3' _chemical_formula_weight 380.81 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.892(9) _cell_length_b 15.074(11) _cell_length_c 9.640(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1728(2) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.570 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.806 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 ccd _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25418 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4281 _reflns_number_gt 3618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0305P)^2^+0.2766P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.049(16) _refine_ls_number_reflns 4281 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.98760(2) 0.251177(17) 0.35684(8) 0.02715(8) Uani 1 1 d . . . Cl1 Cl 1.16340(6) 0.31588(4) 0.26970(8) 0.04431(17) Uani 1 1 d . . . N3 N 1.0307(2) 0.24645(14) 0.5541(3) 0.0335(5) Uani 1 1 d . . . C15 C 1.0383(3) 0.3373(2) 0.6172(3) 0.0447(7) Uani 1 1 d . . . H15A H 1.0186 0.3352 0.7147 0.054 Uiso 1 1 calc R . . H15B H 1.1142 0.3603 0.6087 0.054 Uiso 1 1 calc R . . N2 N 1.02629(18) 0.12295(14) 0.3102(2) 0.0305(4) Uani 1 1 d . . . C14 C 1.1328(2) 0.1953(2) 0.5884(3) 0.0435(7) Uani 1 1 d . . . H14A H 1.1433 0.1956 0.6882 0.052 Uiso 1 1 calc R . . H14B H 1.1975 0.2241 0.5469 0.052 Uiso 1 1 calc R . . N1 N 0.8842(2) 0.26741(15) 0.1990(3) 0.0346(5) Uani 1 1 d . . . C13 C 1.1278(3) 0.10062(18) 0.5388(3) 0.0428(7) Uani 1 1 d . . . H13A H 1.0596 0.0735 0.5740 0.051 Uiso 1 1 calc R . . H13B H 1.1911 0.0684 0.5773 0.051 Uiso 1 1 calc R . . C12 C 1.1298(2) 0.09119(17) 0.3832(3) 0.0391(7) Uani 1 1 d . . . H12A H 1.1939 0.1239 0.3476 0.047 Uiso 1 1 calc R . . H12B H 1.1411 0.0291 0.3606 0.047 Uiso 1 1 calc R . . C11 C 0.9301(2) 0.06519(17) 0.3506(3) 0.0394(6) Uani 1 1 d . . . H11A H 0.9511 0.0041 0.3401 0.059 Uiso 1 1 calc R . . H11B H 0.8667 0.0779 0.2922 0.059 Uiso 1 1 calc R . . H11C H 0.9105 0.0764 0.4456 0.059 Uiso 1 1 calc R . . C10 C 1.0505(3) 0.11232(19) 0.1591(3) 0.0394(6) Uani 1 1 d . . . H10A H 1.0688 0.0506 0.1417 0.047 Uiso 1 1 calc R . . H10B H 1.1166 0.1472 0.1367 0.047 Uiso 1 1 calc R . . C9 C 0.9568(3) 0.1391(2) 0.0624(3) 0.0478(8) Uani 1 1 d . . . H9A H 0.8894 0.1065 0.0874 0.057 Uiso 1 1 calc R . . H9B H 0.9771 0.1221 -0.0313 0.057 Uiso 1 1 calc R . . C8 C 0.9302(3) 0.23738(19) 0.0641(3) 0.0470(8) Uani 1 1 d . . . H8A H 0.9982 0.2705 0.0439 0.056 Uiso 1 1 calc R . . H8B H 0.8761 0.2503 -0.0085 0.056 Uiso 1 1 calc R . . C7 C 0.8412(3) 0.3609(2) 0.1851(4) 0.0485(8) Uani 1 1 d . . . H7A H 0.8830 0.3922 0.1140 0.058 Uiso 1 1 calc R . . H7B H 0.7623 0.3605 0.1595 0.058 Uiso 1 1 calc R . . C2 C 0.8563(2) 0.40471(17) 0.3209(3) 0.0410(7) Uani 1 1 d . . . C1 C 0.9259(2) 0.36235(16) 0.4132(3) 0.0323(5) Uani 1 1 d . . . C6 C 0.9584(2) 0.39449(18) 0.5404(3) 0.0368(6) Uani 1 1 d . . . C5 C 0.9162(3) 0.4773(2) 0.5779(4) 0.0474(7) Uani 1 1 d . . . H5A H 0.9358 0.5022 0.6628 0.057 Uiso 1 1 calc R . . C4 C 0.8449(3) 0.5226(2) 0.4890(4) 0.0520(8) Uani 1 1 d . . . H4A H 0.8167 0.5775 0.5158 0.062 Uiso 1 1 calc R . . C3 C 0.8151(2) 0.48830(18) 0.3622(4) 0.0493(7) Uani 1 1 d . . . H3A H 0.7677 0.5202 0.3037 0.059 Uiso 1 1 calc R . . Cl1X Cl 0.66047(6) 0.14799(5) 0.21446(9) 0.05011(19) Uani 1 1 d . . . H1C H 0.822(3) 0.2307(19) 0.221(3) 0.033(8) Uiso 1 1 d . . . H3C H 0.966(3) 0.208(3) 0.586(4) 0.055(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02832(13) 0.02072(13) 0.03240(14) -0.00176(11) -0.0016(2) 0.00074(11) Cl1 0.0414(3) 0.0322(3) 0.0593(4) 0.0004(3) 0.0149(3) -0.0072(3) N3 0.0323(11) 0.0330(13) 0.0352(13) -0.0020(9) -0.0039(10) -0.0040(9) C15 0.0483(16) 0.0415(17) 0.0445(17) -0.0146(13) -0.0070(13) -0.0051(14) N2 0.0324(10) 0.0224(10) 0.0367(11) 0.0007(8) -0.0009(8) -0.0001(8) C14 0.0385(15) 0.0405(17) 0.0513(17) -0.0013(13) -0.0160(14) -0.0018(12) N1 0.0409(12) 0.0251(11) 0.0378(12) -0.0022(9) -0.0057(10) 0.0023(9) C13 0.0367(15) 0.0350(15) 0.0568(18) 0.0068(13) -0.0159(13) 0.0039(12) C12 0.0325(12) 0.0281(13) 0.057(2) -0.0031(12) -0.0034(12) 0.0031(10) C11 0.0363(12) 0.0298(12) 0.0521(16) 0.0035(14) -0.0092(15) -0.0067(10) C10 0.0488(16) 0.0276(13) 0.0417(15) -0.0061(11) 0.0046(13) 0.0062(13) C9 0.071(2) 0.0342(16) 0.0382(16) -0.0109(12) -0.0022(15) 0.0061(14) C8 0.069(2) 0.0378(17) 0.0347(15) -0.0001(12) -0.0030(15) 0.0079(14) C7 0.0585(18) 0.0292(15) 0.058(2) -0.0023(13) -0.0155(15) 0.0125(13) C2 0.0402(14) 0.0267(13) 0.056(2) -0.0031(12) -0.0036(12) 0.0049(11) C1 0.0301(12) 0.0208(12) 0.0459(14) -0.0062(10) 0.0028(11) 0.0004(10) C6 0.0345(14) 0.0303(14) 0.0457(16) -0.0087(12) 0.0052(12) -0.0048(11) C5 0.0500(17) 0.0392(17) 0.0531(18) -0.0168(13) 0.0098(14) -0.0053(14) C4 0.0504(18) 0.0275(14) 0.078(2) -0.0135(14) 0.0103(17) 0.0028(13) C3 0.0508(16) 0.0286(13) 0.068(2) -0.0051(16) -0.0062(18) 0.0085(11) Cl1X 0.0439(4) 0.0531(4) 0.0534(4) 0.0108(3) -0.0101(4) -0.0023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.908(3) . ? Cu1 N3 1.971(3) . ? Cu1 N1 1.972(3) . ? Cu1 N2 2.037(3) . ? Cu1 Cl1 2.4550(16) . ? N3 C14 1.476(4) . ? N3 C15 1.502(4) . ? C15 C6 1.481(4) . ? N2 C11 1.490(3) . ? N2 C10 1.493(4) . ? N2 C12 1.497(3) . ? C14 C13 1.506(4) . ? N1 C8 1.482(4) . ? N1 C7 1.504(4) . ? C13 C12 1.506(5) . ? C10 C9 1.508(5) . ? C9 C8 1.514(4) . ? C7 C2 1.477(4) . ? C2 C1 1.372(4) . ? C2 C3 1.410(4) . ? C1 C6 1.374(4) . ? C6 C5 1.393(4) . ? C5 C4 1.385(5) . ? C4 C3 1.374(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N3 81.79(12) . . ? C1 Cu1 N1 82.58(11) . . ? N3 Cu1 N1 155.70(11) . . ? C1 Cu1 N2 169.39(10) . . ? N3 Cu1 N2 96.89(9) . . ? N1 Cu1 N2 95.06(9) . . ? C1 Cu1 Cl1 94.35(9) . . ? N3 Cu1 Cl1 97.05(8) . . ? N1 Cu1 Cl1 102.59(10) . . ? N2 Cu1 Cl1 96.26(7) . . ? C14 N3 C15 109.7(2) . . ? C14 N3 Cu1 116.70(19) . . ? C15 N3 Cu1 111.92(18) . . ? C6 C15 N3 106.8(2) . . ? C11 N2 C10 109.9(2) . . ? C11 N2 C12 108.8(2) . . ? C10 N2 C12 105.4(2) . . ? C11 N2 Cu1 108.87(16) . . ? C10 N2 Cu1 111.14(17) . . ? C12 N2 Cu1 112.66(16) . . ? N3 C14 C13 113.0(2) . . ? C8 N1 C7 109.5(2) . . ? C8 N1 Cu1 114.1(2) . . ? C7 N1 Cu1 113.37(18) . . ? C14 C13 C12 113.9(3) . . ? N2 C12 C13 115.2(2) . . ? N2 C10 C9 115.6(2) . . ? C10 C9 C8 114.2(3) . . ? N1 C8 C9 112.6(3) . . ? C2 C7 N1 107.4(2) . . ? C1 C2 C3 116.3(3) . . ? C1 C2 C7 116.1(2) . . ? C3 C2 C7 127.4(3) . . ? C2 C1 C6 125.7(2) . . ? C2 C1 Cu1 117.1(2) . . ? C6 C1 Cu1 117.1(2) . . ? C1 C6 C5 116.5(3) . . ? C1 C6 C15 114.9(2) . . ? C5 C6 C15 128.5(3) . . ? C4 C5 C6 120.1(3) . . ? C3 C4 C5 121.6(3) . . ? C4 C3 C2 119.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Cu1 N3 C14 -151.3(2) . . . . ? N1 Cu1 N3 C14 158.2(2) . . . . ? N2 Cu1 N3 C14 39.3(2) . . . . ? Cl1 Cu1 N3 C14 -57.9(2) . . . . ? C1 Cu1 N3 C15 -23.8(2) . . . . ? N1 Cu1 N3 C15 -74.3(3) . . . . ? N2 Cu1 N3 C15 166.8(2) . . . . ? Cl1 Cu1 N3 C15 69.6(2) . . . . ? C14 N3 C15 C6 159.9(3) . . . . ? Cu1 N3 C15 C6 28.8(3) . . . . ? C1 Cu1 N2 C11 0.9(7) . . . . ? N3 Cu1 N2 C11 83.12(18) . . . . ? N1 Cu1 N2 C11 -75.68(19) . . . . ? Cl1 Cu1 N2 C11 -178.96(16) . . . . ? C1 Cu1 N2 C10 122.1(6) . . . . ? N3 Cu1 N2 C10 -155.68(19) . . . . ? N1 Cu1 N2 C10 45.53(19) . . . . ? Cl1 Cu1 N2 C10 -57.76(18) . . . . ? C1 Cu1 N2 C12 -119.8(6) . . . . ? N3 Cu1 N2 C12 -37.60(19) . . . . ? N1 Cu1 N2 C12 163.60(18) . . . . ? Cl1 Cu1 N2 C12 60.31(18) . . . . ? C15 N3 C14 C13 175.3(3) . . . . ? Cu1 N3 C14 C13 -56.1(3) . . . . ? C1 Cu1 N1 C8 142.0(2) . . . . ? N3 Cu1 N1 C8 -167.7(2) . . . . ? N2 Cu1 N1 C8 -48.4(2) . . . . ? Cl1 Cu1 N1 C8 49.1(2) . . . . ? C1 Cu1 N1 C7 15.7(2) . . . . ? N3 Cu1 N1 C7 66.0(3) . . . . ? N2 Cu1 N1 C7 -174.7(2) . . . . ? Cl1 Cu1 N1 C7 -77.1(2) . . . . ? N3 C14 C13 C12 67.7(3) . . . . ? C11 N2 C12 C13 -65.6(3) . . . . ? C10 N2 C12 C13 176.6(2) . . . . ? Cu1 N2 C12 C13 55.2(3) . . . . ? C14 C13 C12 N2 -69.3(3) . . . . ? C11 N2 C10 C9 62.2(3) . . . . ? C12 N2 C10 C9 179.2(2) . . . . ? Cu1 N2 C10 C9 -58.4(3) . . . . ? N2 C10 C9 C8 66.2(4) . . . . ? C7 N1 C8 C9 -170.2(3) . . . . ? Cu1 N1 C8 C9 61.6(3) . . . . ? C10 C9 C8 N1 -65.8(4) . . . . ? C8 N1 C7 C2 -148.8(3) . . . . ? Cu1 N1 C7 C2 -20.1(3) . . . . ? N1 C7 C2 C1 14.7(4) . . . . ? N1 C7 C2 C3 -171.0(3) . . . . ? C3 C2 C1 C6 -0.2(4) . . . . ? C7 C2 C1 C6 174.8(3) . . . . ? C3 C2 C1 Cu1 -177.7(2) . . . . ? C7 C2 C1 Cu1 -2.7(4) . . . . ? N3 Cu1 C1 C2 -168.8(2) . . . . ? N1 Cu1 C1 C2 -7.5(2) . . . . ? N2 Cu1 C1 C2 -85.2(7) . . . . ? Cl1 Cu1 C1 C2 94.7(2) . . . . ? N3 Cu1 C1 C6 13.5(2) . . . . ? N1 Cu1 C1 C6 174.8(2) . . . . ? N2 Cu1 C1 C6 97.1(6) . . . . ? Cl1 Cu1 C1 C6 -83.0(2) . . . . ? C2 C1 C6 C5 0.1(4) . . . . ? Cu1 C1 C6 C5 177.6(2) . . . . ? C2 C1 C6 C15 -177.3(3) . . . . ? Cu1 C1 C6 C15 0.2(3) . . . . ? N3 C15 C6 C1 -18.8(4) . . . . ? N3 C15 C6 C5 164.2(3) . . . . ? C1 C6 C5 C4 0.3(4) . . . . ? C15 C6 C5 C4 177.3(3) . . . . ? C6 C5 C4 C3 -0.7(5) . . . . ? C5 C4 C3 C2 0.7(5) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C7 C2 C3 C4 -174.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.343 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.057 # Attachment '- 1Br_acml2p112.cif' data_acml2p112 _database_code_depnum_ccdc_archive 'CCDC 735509' #TrackingRef '- 1Br_acml2p112.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 Br Cu N3, Br' _chemical_formula_sum 'C15 H24 Br2 Cu N3' _chemical_formula_weight 469.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.3103(14) _cell_length_b 15.3429(17) _cell_length_c 9.6916(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1830.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 5.556 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.678726 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2.1 2001 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 300(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 ccd _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27574 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4524 _reflns_number_gt 3771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0257P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(9) _refine_ls_number_reflns 4524 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0576 _refine_ls_wR_factor_gt 0.0547 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 Br1 Br 0.67236(2) 0.678126(19) 1.06860(4) 0.05191(9) Uani 1 1 d . . . Cu1 Cu 0.49305(2) 0.752028(19) 0.98857(5) 0.03193(7) Uani 1 1 d . . . C1 C 0.4290(2) 0.64389(16) 0.9332(3) 0.0386(6) Uani 1 1 d . . . C2 C 0.4545(2) 0.6138(2) 0.8037(3) 0.0442(7) Uani 1 1 d . . . N1 N 0.5281(2) 0.75783(14) 0.7900(3) 0.0386(5) Uani 1 1 d . . . H1B H 0.4711 0.7857 0.7496 0.046 Uiso 1 1 d R . . Br2 Br 0.17040(3) 0.85732(2) 0.13153(4) 0.05652(10) Uani 1 1 d . . . C3 C 0.4099(3) 0.5337(2) 0.7653(4) 0.0536(8) Uani 1 1 d . . . H3A H 0.4243 0.5104 0.6787 0.064 Uiso 1 1 calc R . . N2 N 0.53485(18) 0.87676(14) 1.0358(2) 0.0364(5) Uani 1 1 d . . . C4 C 0.3439(3) 0.4892(2) 0.8580(5) 0.0624(10) Uani 1 1 d . . . H4A H 0.3141 0.4359 0.8319 0.075 Uiso 1 1 calc R . . N3 N 0.3985(2) 0.73557(14) 1.1510(3) 0.0389(5) Uani 1 1 d . . . H3B H 0.3389 0.7694 1.1363 0.047 Uiso 1 1 d R . . C5 C 0.3214(2) 0.52159(19) 0.9870(5) 0.0591(9) Uani 1 1 d . . . H5A H 0.2778 0.4902 1.0477 0.071 Uiso 1 1 calc R . . C6 C 0.3649(2) 0.60270(18) 1.0268(3) 0.0461(8) Uani 1 1 d . . . C7 C 0.5319(3) 0.6697(2) 0.7250(3) 0.0503(8) Uani 1 1 d . . . H7A H 0.6048 0.6460 0.7300 0.060 Uiso 1 1 calc R . . H7B H 0.5105 0.6732 0.6288 0.060 Uiso 1 1 calc R . . C8 C 0.6258(3) 0.8074(2) 0.7510(3) 0.0478(8) Uani 1 1 d . . . H8A H 0.6315 0.8085 0.6512 0.057 Uiso 1 1 calc R . . H8B H 0.6894 0.7777 0.7867 0.057 Uiso 1 1 calc R . . C9 C 0.6252(3) 0.90038(19) 0.8045(4) 0.0489(8) Uani 1 1 d . . . H9A H 0.6858 0.9316 0.7638 0.059 Uiso 1 1 calc R . . H9B H 0.5589 0.9287 0.7744 0.059 Uiso 1 1 calc R . . C10 C 0.6330(2) 0.90696(18) 0.9584(3) 0.0459(8) Uani 1 1 d . . . H10A H 0.6950 0.8730 0.9889 0.055 Uiso 1 1 calc R . . H10B H 0.6469 0.9673 0.9827 0.055 Uiso 1 1 calc R . . C11 C 0.4419(2) 0.93508(18) 1.0003(3) 0.0431(6) Uani 1 1 d . . . H11A H 0.4608 0.9943 1.0211 0.065 Uiso 1 1 calc R . . H11B H 0.3793 0.9185 1.0533 0.065 Uiso 1 1 calc R . . H11C H 0.4257 0.9299 0.9038 0.065 Uiso 1 1 calc R . . C12 C 0.5616(3) 0.8861(2) 1.1853(3) 0.0481(7) Uani 1 1 d . . . H12A H 0.5809 0.9464 1.2026 0.058 Uiso 1 1 calc R . . H12B H 0.6253 0.8509 1.2047 0.058 Uiso 1 1 calc R . . C13 C 0.4724(3) 0.8602(2) 1.2861(4) 0.0554(9) Uani 1 1 d . . . H13A H 0.4949 0.8763 1.3786 0.066 Uiso 1 1 calc R . . H13B H 0.4073 0.8931 1.2644 0.066 Uiso 1 1 calc R . . C14 C 0.4452(3) 0.7646(2) 1.2846(3) 0.0528(8) Uani 1 1 d . . . H14A H 0.5106 0.7313 1.3033 0.063 Uiso 1 1 calc R . . H14B H 0.3936 0.7524 1.3577 0.063 Uiso 1 1 calc R . . C15 C 0.3571(3) 0.6432(2) 1.1663(4) 0.0553(9) Uani 1 1 d . . . H15A H 0.4011 0.6113 1.2321 0.066 Uiso 1 1 calc R . . H15B H 0.2824 0.6433 1.1982 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 Br1 0.04780(17) 0.03738(15) 0.0705(2) -0.00072(16) -0.01751(17) 0.00941(12) Cu1 0.03319(15) 0.02387(13) 0.03873(14) -0.00210(13) 0.00180(15) -0.00063(12) C1 0.0396(15) 0.0240(13) 0.0523(17) -0.0047(12) -0.0032(13) -0.0044(11) C2 0.0452(18) 0.0334(15) 0.0541(18) -0.0079(14) -0.0060(15) 0.0027(13) N1 0.0400(13) 0.0345(13) 0.0413(13) 0.0008(10) 0.0011(11) 0.0020(10) Br2 0.04782(19) 0.0575(2) 0.0642(2) 0.01240(17) 0.01142(17) 0.00397(15) C3 0.057(2) 0.0437(17) 0.060(2) -0.0204(16) -0.0074(17) 0.0039(16) N2 0.0372(12) 0.0258(10) 0.0461(14) -0.0026(9) 0.0022(10) 0.0004(9) C4 0.060(2) 0.0325(16) 0.094(3) -0.0196(18) -0.004(2) -0.0085(15) N3 0.0442(14) 0.0301(12) 0.0423(13) -0.0020(10) 0.0084(11) -0.0023(9) C5 0.0569(19) 0.0330(15) 0.088(3) -0.0109(18) 0.011(2) -0.0157(13) C6 0.0443(16) 0.0299(14) 0.064(2) -0.0059(13) 0.0065(14) -0.0055(12) C7 0.061(2) 0.0439(18) 0.0458(18) -0.0127(14) 0.0039(16) 0.0018(15) C8 0.0449(17) 0.0479(18) 0.0505(18) -0.0022(15) 0.0177(15) 0.0021(14) C9 0.0457(17) 0.0386(17) 0.062(2) 0.0065(15) 0.0174(16) -0.0041(14) C10 0.0357(15) 0.0326(16) 0.069(2) -0.0007(14) 0.0053(14) -0.0021(11) C11 0.0428(16) 0.0314(13) 0.0551(17) 0.0041(14) 0.0076(15) 0.0077(12) C12 0.057(2) 0.0350(15) 0.0524(18) -0.0076(14) -0.0069(16) -0.0046(15) C13 0.082(2) 0.0396(18) 0.0447(19) -0.0099(14) 0.0002(17) -0.0066(17) C14 0.073(2) 0.0407(17) 0.0452(18) -0.0009(14) 0.0058(17) -0.0066(16) C15 0.068(2) 0.0332(16) 0.064(2) -0.0039(15) 0.0214(18) -0.0114(15) _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 Br1 Cu1 2.5999(5) . ? Cu1 C1 1.914(3) . ? Cu1 N3 1.974(2) . ? Cu1 N1 1.974(3) . ? Cu1 N2 2.034(2) . ? C1 C6 1.359(4) . ? C1 C2 1.374(4) . ? C2 C3 1.395(4) . ? C2 C7 1.492(4) . ? N1 C8 1.473(4) . ? N1 C7 1.492(4) . ? C3 C4 1.392(5) . ? N2 C12 1.493(4) . ? N2 C11 1.493(3) . ? N2 C10 1.496(4) . ? C4 C5 1.374(6) . ? N3 C14 1.485(4) . ? N3 C15 1.513(4) . ? C5 C6 1.408(4) . ? C6 C15 1.491(5) . ? C8 C9 1.517(4) . ? C9 C10 1.499(5) . ? C12 C13 1.522(5) . ? C13 C14 1.505(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N3 82.53(12) . . ? C1 Cu1 N1 81.69(12) . . ? N3 Cu1 N1 155.78(10) . . ? C1 Cu1 N2 169.44(11) . . ? N3 Cu1 N2 95.17(9) . . ? N1 Cu1 N2 96.98(10) . . ? C1 Cu1 Br1 93.18(9) . . ? N3 Cu1 Br1 101.94(7) . . ? N1 Cu1 Br1 97.18(7) . . ? N2 Cu1 Br1 97.38(7) . . ? C6 C1 C2 125.9(3) . . ? C6 C1 Cu1 117.1(2) . . ? C2 C1 Cu1 117.0(2) . . ? C1 C2 C3 116.7(3) . . ? C1 C2 C7 114.8(3) . . ? C3 C2 C7 128.4(3) . . ? C8 N1 C7 109.5(2) . . ? C8 N1 Cu1 116.9(2) . . ? C7 N1 Cu1 112.20(19) . . ? C4 C3 C2 119.4(3) . . ? C12 N2 C11 109.6(2) . . ? C12 N2 C10 106.2(2) . . ? C11 N2 C10 108.6(2) . . ? C12 N2 Cu1 111.35(18) . . ? C11 N2 Cu1 108.55(17) . . ? C10 N2 Cu1 112.54(17) . . ? C5 C4 C3 121.8(3) . . ? C14 N3 C15 109.0(2) . . ? C14 N3 Cu1 115.4(2) . . ? C15 N3 Cu1 113.36(18) . . ? C4 C5 C6 119.5(3) . . ? C1 C6 C5 116.7(3) . . ? C1 C6 C15 116.7(3) . . ? C5 C6 C15 126.3(3) . . ? N1 C7 C2 106.6(2) . . ? N1 C8 C9 113.2(2) . . ? C10 C9 C8 113.7(3) . . ? N2 C10 C9 115.2(3) . . ? N2 C12 C13 116.0(3) . . ? C14 C13 C12 114.1(3) . . ? N3 C14 C13 112.7(3) . . ? C6 C15 N3 106.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 C1 C6 -7.4(2) . . . . ? N1 Cu1 C1 C6 -168.9(3) . . . . ? N2 Cu1 C1 C6 -85.4(7) . . . . ? Br1 Cu1 C1 C6 94.3(2) . . . . ? N3 Cu1 C1 C2 174.4(3) . . . . ? N1 Cu1 C1 C2 12.8(2) . . . . ? N2 Cu1 C1 C2 96.3(7) . . . . ? Br1 Cu1 C1 C2 -84.0(2) . . . . ? C6 C1 C2 C3 0.2(5) . . . . ? Cu1 C1 C2 C3 178.3(2) . . . . ? C6 C1 C2 C7 -176.7(3) . . . . ? Cu1 C1 C2 C7 1.4(4) . . . . ? C1 Cu1 N1 C8 -151.8(2) . . . . ? N3 Cu1 N1 C8 158.4(2) . . . . ? N2 Cu1 N1 C8 38.8(2) . . . . ? Br1 Cu1 N1 C8 -59.6(2) . . . . ? C1 Cu1 N1 C7 -24.1(2) . . . . ? N3 Cu1 N1 C7 -73.9(3) . . . . ? N2 Cu1 N1 C7 166.5(2) . . . . ? Br1 Cu1 N1 C7 68.1(2) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C7 C2 C3 C4 176.1(3) . . . . ? C1 Cu1 N2 C12 121.2(7) . . . . ? N3 Cu1 N2 C12 44.2(2) . . . . ? N1 Cu1 N2 C12 -156.7(2) . . . . ? Br1 Cu1 N2 C12 -58.53(19) . . . . ? C1 Cu1 N2 C11 0.4(7) . . . . ? N3 Cu1 N2 C11 -76.49(19) . . . . ? N1 Cu1 N2 C11 82.52(19) . . . . ? Br1 Cu1 N2 C11 -179.26(17) . . . . ? C1 Cu1 N2 C10 -119.8(7) . . . . ? N3 Cu1 N2 C10 163.30(19) . . . . ? N1 Cu1 N2 C10 -37.7(2) . . . . ? Br1 Cu1 N2 C10 60.53(19) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C1 Cu1 N3 C14 143.5(2) . . . . ? N1 Cu1 N3 C14 -166.8(2) . . . . ? N2 Cu1 N3 C14 -46.9(2) . . . . ? Br1 Cu1 N3 C14 51.8(2) . . . . ? C1 Cu1 N3 C15 16.8(2) . . . . ? N1 Cu1 N3 C15 66.5(3) . . . . ? N2 Cu1 N3 C15 -173.6(2) . . . . ? Br1 Cu1 N3 C15 -74.9(2) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? Cu1 C1 C6 C5 -177.7(2) . . . . ? C2 C1 C6 C15 174.1(3) . . . . ? Cu1 C1 C6 C15 -4.0(4) . . . . ? C4 C5 C6 C1 -0.9(5) . . . . ? C4 C5 C6 C15 -174.0(3) . . . . ? C8 N1 C7 C2 161.1(3) . . . . ? Cu1 N1 C7 C2 29.6(3) . . . . ? C1 C2 C7 N1 -20.0(4) . . . . ? C3 C2 C7 N1 163.5(3) . . . . ? C7 N1 C8 C9 176.0(3) . . . . ? Cu1 N1 C8 C9 -55.0(3) . . . . ? N1 C8 C9 C10 67.1(4) . . . . ? C12 N2 C10 C9 178.1(3) . . . . ? C11 N2 C10 C9 -64.2(3) . . . . ? Cu1 N2 C10 C9 56.0(3) . . . . ? C8 C9 C10 N2 -69.6(4) . . . . ? C11 N2 C12 C13 62.1(3) . . . . ? C10 N2 C12 C13 179.2(2) . . . . ? Cu1 N2 C12 C13 -58.0(3) . . . . ? N2 C12 C13 C14 66.2(4) . . . . ? C15 N3 C14 C13 -170.9(3) . . . . ? Cu1 N3 C14 C13 60.2(3) . . . . ? C12 C13 C14 N3 -64.6(4) . . . . ? C1 C6 C15 N3 16.5(4) . . . . ? C5 C6 C15 N3 -170.4(3) . . . . ? C14 N3 C15 C6 -151.8(3) . . . . ? Cu1 N3 C15 C6 -21.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.407 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.056 # Attachment '- 1I_acml3p101_last.cif' data_acml3p101 _database_code_depnum_ccdc_archive 'CCDC 735510' #TrackingRef '- 1I_acml3p101_last.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 Cu I N3, I' _chemical_formula_sum 'C15 H24 Cu I2 N3' _chemical_formula_weight 563.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1650(6) _cell_length_b 17.7756(14) _cell_length_c 15.0327(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.2740(10) _cell_angle_gamma 90.00 _cell_volume 1889.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 5188 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.02 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.982 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 4.421 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.690579 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 ccd _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29056 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4675 _reflns_number_gt 3728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0286P)^2^+0.5874P] 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 4675 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 I2 I 0.07104(3) 0.726663(11) 0.422868(14) 0.05286(7) Uani 1 1 d . . . N3 N 0.3387(4) 0.33140(14) 0.15909(16) 0.0435(6) Uani 1 1 d . . . H3 H 0.236(4) 0.3108(15) 0.1494(18) 0.030(7) Uiso 1 1 d . . . I1 I 0.68634(3) 0.469002(14) 0.286933(15) 0.05960(8) Uani 1 1 d . . . Cu1 Cu 0.30536(4) 0.409104(17) 0.24841(2) 0.03155(8) Uani 1 1 d . . . N1 N 0.1812(3) 0.49350(13) 0.30086(17) 0.0400(5) Uani 1 1 d . . . H1 H 0.073(5) 0.4812(16) 0.292(2) 0.043(9) Uiso 1 1 d . . . C1 C 0.2625(4) 0.47186(16) 0.14439(19) 0.0406(6) Uani 1 1 d . . . N2 N 0.3033(3) 0.33727(14) 0.35213(15) 0.0421(5) Uani 1 1 d . . . C8 C 0.2372(5) 0.50741(19) 0.3985(2) 0.0526(8) Uani 1 1 d . . . H8B H 0.1628 0.5487 0.4162 0.063 Uiso 1 1 calc R . . H8A H 0.3692 0.5223 0.4102 0.063 Uiso 1 1 calc R . . C2 C 0.2021(4) 0.54408(17) 0.1558(2) 0.0493(7) Uani 1 1 d . . . C6 C 0.2954(4) 0.4410(2) 0.0641(2) 0.0498(7) Uani 1 1 d . . . C9 C 0.2100(5) 0.4391(2) 0.4549(2) 0.0556(8) Uani 1 1 d . . . H9B H 0.2307 0.4536 0.5179 0.067 Uiso 1 1 calc R . . H9A H 0.0801 0.4222 0.4397 0.067 Uiso 1 1 calc R . . C10 C 0.3395(5) 0.3744(2) 0.4427(2) 0.0542(8) Uani 1 1 d . . . H10B H 0.4688 0.3926 0.4533 0.065 Uiso 1 1 calc R . . H10A H 0.3281 0.3368 0.4883 0.065 Uiso 1 1 calc R . . C7 C 0.1894(5) 0.56504(18) 0.2488(3) 0.0578(8) Uani 1 1 d . . . H7B H 0.0767 0.5949 0.2506 0.069 Uiso 1 1 calc R . . H7A H 0.2990 0.5944 0.2745 0.069 Uiso 1 1 calc R . . C11 C 0.1102(5) 0.30189(18) 0.3389(2) 0.0534(8) Uani 1 1 d . . . H11C H 0.1024 0.2671 0.3870 0.080 Uiso 1 1 calc R . . H11B H 0.0889 0.2756 0.2824 0.080 Uiso 1 1 calc R . . H11A H 0.0161 0.3403 0.3387 0.080 Uiso 1 1 calc R . . C3 C 0.1717(5) 0.5893(2) 0.0785(3) 0.0644(10) Uani 1 1 d . . . H3A H 0.1321 0.6388 0.0825 0.077 Uiso 1 1 calc R . . C12 C 0.4506(5) 0.2775(2) 0.3552(3) 0.0646(10) Uani 1 1 d . . . H12B H 0.4419 0.2448 0.4061 0.078 Uiso 1 1 calc R . . H12A H 0.5740 0.3012 0.3661 0.078 Uiso 1 1 calc R . . C13 C 0.4380(6) 0.2295(2) 0.2716(3) 0.0771(12) Uani 1 1 d . . . H13B H 0.3117 0.2085 0.2578 0.093 Uiso 1 1 calc R . . H13A H 0.5263 0.1880 0.2837 0.093 Uiso 1 1 calc R . . C15 C 0.3704(5) 0.3638(2) 0.0709(2) 0.0622(9) Uani 1 1 d . . . H15B H 0.5044 0.3643 0.0675 0.075 Uiso 1 1 calc R . . H15A H 0.3063 0.3335 0.0216 0.075 Uiso 1 1 calc R . . C5 C 0.2629(5) 0.4879(3) -0.0120(2) 0.0680(11) Uani 1 1 d . . . H5A H 0.2833 0.4702 -0.0678 0.082 Uiso 1 1 calc R . . C14 C 0.4809(5) 0.2725(2) 0.1896(3) 0.0658(10) Uani 1 1 d . . . H14B H 0.6046 0.2957 0.2042 0.079 Uiso 1 1 calc R . . H14A H 0.4854 0.2373 0.1406 0.079 Uiso 1 1 calc R . . C4 C 0.2001(5) 0.5608(3) -0.0030(3) 0.0736(12) Uani 1 1 d . . . H4A H 0.1765 0.5913 -0.0538 0.088 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 I2 0.05755(14) 0.05023(12) 0.05435(13) 0.00166(9) 0.01979(10) 0.00777(9) N3 0.0443(14) 0.0482(14) 0.0414(13) -0.0086(11) 0.0169(11) -0.0059(11) I1 0.02805(11) 0.09573(19) 0.05473(14) -0.01012(11) 0.00583(8) -0.00825(10) Cu1 0.02949(16) 0.03710(17) 0.02905(16) 0.00005(12) 0.00772(12) 0.00042(12) N1 0.0307(13) 0.0405(13) 0.0507(14) -0.0040(10) 0.0126(10) -0.0034(10) C1 0.0322(13) 0.0538(17) 0.0353(14) 0.0101(12) 0.0043(11) -0.0104(12) N2 0.0444(13) 0.0483(13) 0.0339(12) 0.0056(10) 0.0070(10) 0.0045(10) C8 0.0514(18) 0.0579(19) 0.0513(18) -0.0240(15) 0.0165(14) -0.0060(14) C2 0.0350(15) 0.0495(17) 0.062(2) 0.0179(15) 0.0032(13) -0.0072(12) C6 0.0413(16) 0.072(2) 0.0366(15) 0.0055(14) 0.0071(12) -0.0184(15) C9 0.060(2) 0.076(2) 0.0332(15) -0.0103(15) 0.0149(14) -0.0067(17) C10 0.0562(19) 0.074(2) 0.0312(15) 0.0051(14) 0.0041(13) 0.0017(16) C7 0.061(2) 0.0400(16) 0.075(2) 0.0072(16) 0.0186(17) 0.0028(14) C11 0.060(2) 0.0538(18) 0.0484(18) 0.0048(14) 0.0154(15) -0.0099(15) C3 0.0427(18) 0.070(2) 0.079(3) 0.036(2) 0.0035(17) -0.0049(15) C12 0.070(2) 0.061(2) 0.062(2) 0.0212(17) 0.0097(18) 0.0257(18) C13 0.092(3) 0.054(2) 0.088(3) 0.006(2) 0.023(2) 0.036(2) C15 0.070(2) 0.080(2) 0.0436(18) -0.0149(16) 0.0293(16) -0.0261(19) C5 0.050(2) 0.116(3) 0.0359(17) 0.0129(19) 0.0039(14) -0.035(2) C14 0.061(2) 0.069(2) 0.071(2) -0.0182(18) 0.0209(18) 0.0182(17) C4 0.0454(19) 0.101(3) 0.069(3) 0.045(2) -0.0069(17) -0.022(2) _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 N3 C14 1.482(4) . ? N3 C15 1.496(4) . ? N3 Cu1 1.968(2) . ? N3 H3 0.81(3) . ? I1 Cu1 2.9001(4) . ? Cu1 C1 1.905(3) . ? Cu1 N1 1.972(2) . ? Cu1 N2 2.017(2) . ? N1 C8 1.478(4) . ? N1 C7 1.500(4) . ? N1 H1 0.79(3) . ? C1 C2 1.374(4) . ? C1 C6 1.380(4) . ? N2 C12 1.493(4) . ? N2 C10 1.498(4) . ? N2 C11 1.503(4) . ? C8 C9 1.512(5) . ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C2 C3 1.400(4) . ? C2 C7 1.464(5) . ? C6 C5 1.403(5) . ? C6 C15 1.472(5) . ? C9 C10 1.507(5) . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? C11 H11A 0.9600 . ? C3 C4 1.371(6) . ? C3 H3A 0.9300 . ? C12 C13 1.510(6) . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C13 C14 1.523(5) . ? C13 H13B 0.9700 . ? C13 H13A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? C5 C4 1.386(6) . ? C5 H5A 0.9300 . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C4 H4A 0.9300 . ? 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 C14 N3 C15 110.6(3) . . ? C14 N3 Cu1 116.0(2) . . ? C15 N3 Cu1 112.8(2) . . ? C14 N3 H3 107.1(19) . . ? C15 N3 H3 106(2) . . ? Cu1 N3 H3 103.4(19) . . ? C1 Cu1 N3 82.65(12) . . ? C1 Cu1 N1 81.92(12) . . ? N3 Cu1 N1 156.78(11) . . ? C1 Cu1 N2 170.01(11) . . ? N3 Cu1 N2 95.74(10) . . ? N1 Cu1 N2 96.46(10) . . ? C1 Cu1 I1 88.33(8) . . ? N3 Cu1 I1 100.38(8) . . ? N1 Cu1 I1 96.41(7) . . ? N2 Cu1 I1 101.65(7) . . ? C8 N1 C7 110.4(2) . . ? C8 N1 Cu1 117.15(19) . . ? C7 N1 Cu1 112.22(19) . . ? C8 N1 H1 108(2) . . ? C7 N1 H1 105(2) . . ? Cu1 N1 H1 102(2) . . ? C2 C1 C6 125.5(3) . . ? C2 C1 Cu1 117.2(2) . . ? C6 C1 Cu1 117.3(2) . . ? C12 N2 C10 105.5(2) . . ? C12 N2 C11 109.7(3) . . ? C10 N2 C11 109.0(2) . . ? C12 N2 Cu1 112.44(19) . . ? C10 N2 Cu1 113.70(19) . . ? C11 N2 Cu1 106.47(17) . . ? N1 C8 C9 112.6(2) . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? H8B C8 H8A 107.8 . . ? C1 C2 C3 116.3(3) . . ? C1 C2 C7 115.2(3) . . ? C3 C2 C7 128.4(3) . . ? C1 C6 C5 116.6(3) . . ? C1 C6 C15 114.9(3) . . ? C5 C6 C15 128.3(3) . . ? C10 C9 C8 114.0(3) . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? H9B C9 H9A 107.6 . . ? N2 C10 C9 115.3(2) . . ? N2 C10 H10B 108.5 . . ? C9 C10 H10B 108.5 . . ? N2 C10 H10A 108.5 . . ? C9 C10 H10A 108.5 . . ? H10B C10 H10A 107.5 . . ? C2 C7 N1 107.3(3) . . ? C2 C7 H7B 110.3 . . ? N1 C7 H7B 110.3 . . ? C2 C7 H7A 110.3 . . ? N1 C7 H7A 110.3 . . ? H7B C7 H7A 108.5 . . ? N2 C11 H11C 109.5 . . ? N2 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? N2 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? N2 C12 C13 115.4(3) . . ? N2 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? N2 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? H12B C12 H12A 107.5 . . ? C12 C13 C14 113.5(3) . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? H13B C13 H13A 107.7 . . ? C6 C15 N3 108.3(3) . . ? C6 C15 H15B 110.0 . . ? N3 C15 H15B 110.0 . . ? C6 C15 H15A 110.0 . . ? N3 C15 H15A 110.0 . . ? H15B C15 H15A 108.4 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? N3 C14 C13 112.7(3) . . ? N3 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? N3 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? H14B C14 H14A 107.8 . . ? C3 C4 C5 122.0(3) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? 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 C14 N3 Cu1 C1 145.6(2) . . . . ? C15 N3 Cu1 C1 16.7(2) . . . . ? C14 N3 Cu1 N1 -165.7(3) . . . . ? C15 N3 Cu1 N1 65.4(4) . . . . ? C14 N3 Cu1 N2 -44.3(2) . . . . ? C15 N3 Cu1 N2 -173.2(2) . . . . ? C14 N3 Cu1 I1 58.7(2) . . . . ? C15 N3 Cu1 I1 -70.2(2) . . . . ? C1 Cu1 N1 C8 -150.0(2) . . . . ? N3 Cu1 N1 C8 161.2(2) . . . . ? N2 Cu1 N1 C8 39.9(2) . . . . ? I1 Cu1 N1 C8 -62.6(2) . . . . ? C1 Cu1 N1 C7 -20.7(2) . . . . ? N3 Cu1 N1 C7 -69.5(3) . . . . ? N2 Cu1 N1 C7 169.2(2) . . . . ? I1 Cu1 N1 C7 66.7(2) . . . . ? N3 Cu1 C1 C2 172.5(2) . . . . ? N1 Cu1 C1 C2 9.9(2) . . . . ? N2 Cu1 C1 C2 91.2(7) . . . . ? I1 Cu1 C1 C2 -86.8(2) . . . . ? N3 Cu1 C1 C6 -7.7(2) . . . . ? N1 Cu1 C1 C6 -170.3(2) . . . . ? N2 Cu1 C1 C6 -89.0(7) . . . . ? I1 Cu1 C1 C6 93.0(2) . . . . ? C1 Cu1 N2 C12 122.5(6) . . . . ? N3 Cu1 N2 C12 42.4(2) . . . . ? N1 Cu1 N2 C12 -157.4(2) . . . . ? I1 Cu1 N2 C12 -59.5(2) . . . . ? C1 Cu1 N2 C10 -117.6(7) . . . . ? N3 Cu1 N2 C10 162.2(2) . . . . ? N1 Cu1 N2 C10 -37.6(2) . . . . ? I1 Cu1 N2 C10 60.33(19) . . . . ? C1 Cu1 N2 C11 2.4(7) . . . . ? N3 Cu1 N2 C11 -77.8(2) . . . . ? N1 Cu1 N2 C11 82.45(19) . . . . ? I1 Cu1 N2 C11 -179.62(17) . . . . ? C7 N1 C8 C9 173.4(3) . . . . ? Cu1 N1 C8 C9 -56.4(3) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? Cu1 C1 C2 C3 179.9(2) . . . . ? C6 C1 C2 C7 -176.2(3) . . . . ? Cu1 C1 C2 C7 3.6(3) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? Cu1 C1 C6 C5 179.9(2) . . . . ? C2 C1 C6 C15 176.5(3) . . . . ? Cu1 C1 C6 C15 -3.3(3) . . . . ? N1 C8 C9 C10 66.9(4) . . . . ? C12 N2 C10 C9 178.3(3) . . . . ? C11 N2 C10 C9 -64.0(3) . . . . ? Cu1 N2 C10 C9 54.6(3) . . . . ? C8 C9 C10 N2 -67.9(4) . . . . ? C1 C2 C7 N1 -19.6(4) . . . . ? C3 C2 C7 N1 164.6(3) . . . . ? C8 N1 C7 C2 159.5(3) . . . . ? Cu1 N1 C7 C2 26.8(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C7 C2 C3 C4 176.5(3) . . . . ? C10 N2 C12 C13 177.6(3) . . . . ? C11 N2 C12 C13 60.3(4) . . . . ? Cu1 N2 C12 C13 -57.9(4) . . . . ? N2 C12 C13 C14 67.3(5) . . . . ? C1 C6 C15 N3 16.2(4) . . . . ? C5 C6 C15 N3 -167.4(3) . . . . ? C14 N3 C15 C6 -153.5(3) . . . . ? Cu1 N3 C15 C6 -21.9(3) . . . . ? C1 C6 C5 C4 -0.3(4) . . . . ? C15 C6 C5 C4 -176.7(3) . . . . ? C15 N3 C14 C13 -171.4(3) . . . . ? Cu1 N3 C14 C13 58.6(4) . . . . ? C12 C13 C14 N3 -65.6(5) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C6 C5 C4 C3 1.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.069 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.078 # Attachment '- 2Cl_acml1p87_last.cif' data_acml1p87 _database_code_depnum_ccdc_archive 'CCDC 735511' #TrackingRef '- 2Cl_acml1p87_last.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cl Cu N3, H2 O, Cl' _chemical_formula_sum 'C14 H24 Cl2 Cu N3 O' _chemical_formula_weight 384.80 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.470(2) _cell_length_b 15.254(3) _cell_length_c 9.0700(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1725.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description nedlee _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 1.577 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.51 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS v2.10 BRUKER 2001' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24670 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4186 _reflns_number_gt 3862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER Shelxtl' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. The C-H H-atoms were placed in geometrically optimized positions, and forced to ride on the atom to which they are attached, with Uiso (H) = 1.2 (C). The amino and the H2O H-atoms, were located in the diference Fourier map. The H-O distance was constrained to 0.96 (0.001)A, and the N-H distance was refined freely. A riding model was applied to these atoms with Uiso (H) = 1.2 (N) for amino H-atoms and Uiso (H) = 1.5 (O) for H2O Hydrogen atoms ; _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^)+(0.0892P)^2^+1.0137P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(3) _refine_ls_number_reflns 4186 _refine_ls_number_parameters 194 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.005 _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 0.00030(3) 0.24626(2) 0.7075(2) 0.03242(14) Uani 1 1 d . . . Cl1 Cl 0.17256(6) 0.17941(5) 0.78014(10) 0.03648(18) Uani 1 1 d . . . C2 C -0.0431(3) 0.1061(3) 0.5160(4) 0.0419(8) Uani 1 1 d . . . C1 C -0.0641(3) 0.1378(2) 0.6555(5) 0.0380(7) Uani 1 1 d . . . N2 N 0.0440(2) 0.36966(19) 0.7513(4) 0.0421(7) Uani 1 1 d . . . H2 H -0.009(3) 0.3998(19) 0.7340(12) 0.050 Uiso 1 1 d R . . N3 N -0.0923(3) 0.2333(2) 0.8826(4) 0.0407(7) Uani 1 1 d . . . H3 H -0.142(4) 0.261(2) 0.8668(12) 0.049 Uiso 1 1 d R . . C6 C -0.1274(3) 0.0974(2) 0.7592(5) 0.0449(8) Uani 1 1 d . . . C5 C -0.1729(3) 0.0168(3) 0.7202(6) 0.0524(10) Uani 1 1 d . . . H5A H -0.2156 -0.0134 0.7873 0.063 Uiso 1 1 calc R . . C4 C -0.1543(4) -0.0181(3) 0.5815(6) 0.0558(11) Uani 1 1 d . . . H4A H -0.1854 -0.0714 0.5562 0.067 Uiso 1 1 calc R . . C3 C -0.0892(4) 0.0256(3) 0.4783(5) 0.0520(10) Uani 1 1 d . . . H3A H -0.0769 0.0012 0.3859 0.062 Uiso 1 1 calc R . . C7 C 0.0313(4) 0.1606(3) 0.4276(5) 0.0502(9) Uani 1 1 d . . . H7A H 0.0100 0.1608 0.3247 0.060 Uiso 1 1 calc R . . H7B H 0.1039 0.1382 0.4346 0.060 Uiso 1 1 calc R . . C8 C 0.1147(4) 0.3054(3) 0.4400(6) 0.0551(11) Uani 1 1 d . . . H8A H 0.1149 0.3064 0.3331 0.066 Uiso 1 1 calc R . . H8B H 0.1814 0.2788 0.4723 0.066 Uiso 1 1 calc R . . C9 C 0.1092(4) 0.3971(3) 0.4964(6) 0.0561(11) Uani 1 1 d . . . H9A H 0.0385 0.4206 0.4756 0.067 Uiso 1 1 calc R . . H9B H 0.1610 0.4325 0.4432 0.067 Uiso 1 1 calc R . . C10 C 0.1307(3) 0.4054(3) 0.6583(6) 0.0545(11) Uani 1 1 d . . . H10A H 0.1969 0.3749 0.6814 0.065 Uiso 1 1 calc R . . H10B H 0.1407 0.4668 0.6822 0.065 Uiso 1 1 calc R . . C12 C -0.0225(4) 0.3642(3) 1.0123(6) 0.0573(11) Uani 1 1 d . . . H12A H -0.0053 0.3858 1.1100 0.069 Uiso 1 1 calc R . . H12B H -0.0860 0.3950 0.9786 0.069 Uiso 1 1 calc R . . C13 C -0.0477(4) 0.2678(3) 1.0223(5) 0.0533(10) Uani 1 1 d . . . H13A H 0.0173 0.2360 1.0466 0.064 Uiso 1 1 calc R . . H13B H -0.0990 0.2583 1.1011 0.064 Uiso 1 1 calc R . . C14 C -0.1320(4) 0.1414(3) 0.9048(5) 0.0539(11) Uani 1 1 d . . . H14A H -0.0871 0.1108 0.9754 0.065 Uiso 1 1 calc R . . H14B H -0.2050 0.1420 0.9416 0.065 Uiso 1 1 calc R . . Cl2 Cl 0.68608(9) 0.34639(9) 0.86192(15) 0.0588(3) Uani 1 1 d . . . N1 N 0.0246(3) 0.2515(2) 0.4913(5) 0.0416(8) Uani 1 1 d . . . H1 H -0.033(4) 0.2752(16) 0.454(3) 0.050 Uiso 1 1 d R . . C11 C 0.0702(4) 0.3853(3) 0.9089(6) 0.0570(11) Uani 1 1 d . . . H11A H 0.0903 0.4463 0.9216 0.068 Uiso 1 1 calc R . . H11B H 0.1315 0.3496 0.9358 0.068 Uiso 1 1 calc R . . O1W O 0.8424(3) 0.4537(3) 0.6590(5) 0.0665(9) Uani 1 1 d D . . H1W H 0.7895 0.4213 0.7133 0.100 Uiso 1 1 d RD . . H2W H 0.8137 0.4394 0.5638 0.100 Uiso 1 1 d RD . . 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 0.0291(2) 0.0283(2) 0.0398(3) -0.00187(19) 0.00052(14) -0.00086(13) Cl1 0.0283(3) 0.0279(3) 0.0532(4) 0.0014(3) -0.0126(3) 0.0089(3) C2 0.0372(18) 0.0421(18) 0.046(2) -0.0066(15) -0.0019(15) 0.0006(14) C1 0.0334(15) 0.0314(15) 0.0493(19) -0.0049(14) -0.0015(14) -0.0030(12) N2 0.0319(14) 0.0319(13) 0.062(2) -0.0037(13) -0.0033(14) 0.0009(11) N3 0.0399(16) 0.0377(14) 0.0444(17) -0.0039(13) 0.0047(13) 0.0013(12) C6 0.0435(18) 0.0369(16) 0.054(2) -0.0018(15) 0.0040(16) -0.0043(14) C5 0.045(2) 0.0378(17) 0.074(3) 0.0005(19) 0.006(2) -0.0082(15) C4 0.050(2) 0.040(2) 0.077(3) -0.011(2) -0.006(2) -0.0097(17) C3 0.055(2) 0.045(2) 0.056(3) -0.0151(18) -0.008(2) -0.0005(18) C7 0.060(3) 0.047(2) 0.043(2) -0.0055(17) 0.0096(19) 0.0028(19) C8 0.045(2) 0.056(2) 0.064(3) 0.011(2) 0.018(2) 0.0000(19) C9 0.045(2) 0.044(2) 0.080(3) 0.017(2) 0.014(2) -0.0040(17) C10 0.0369(19) 0.0421(19) 0.084(3) 0.001(2) 0.0027(19) -0.0092(16) C12 0.062(3) 0.051(3) 0.059(3) -0.020(2) -0.005(2) -0.002(2) C13 0.062(3) 0.054(2) 0.044(2) -0.0082(18) 0.000(2) 0.007(2) C14 0.066(3) 0.042(2) 0.054(2) -0.0010(17) 0.019(2) -0.0082(19) Cl2 0.0395(5) 0.0739(7) 0.0630(7) 0.0081(6) 0.0048(4) -0.0032(4) N1 0.0393(15) 0.0432(19) 0.042(2) 0.0049(12) 0.0044(16) 0.0024(12) C11 0.046(2) 0.050(2) 0.075(3) -0.020(2) -0.010(2) -0.0018(18) O1W 0.0465(16) 0.077(2) 0.076(2) 0.0147(19) 0.0057(15) 0.0072(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.898(3) . ? Cu1 N3 1.974(4) . ? Cu1 N1 1.986(5) . ? Cu1 N2 1.999(3) . ? Cu1 Cl1 2.4675(10) . ? C2 C1 1.379(6) . ? C2 C3 1.398(6) . ? C2 C7 1.482(6) . ? C1 C6 1.374(6) . ? N2 C10 1.476(5) . ? N2 C11 1.486(6) . ? N2 H2 0.8168 . ? N3 C13 1.480(6) . ? N3 C14 1.500(5) . ? N3 H3 0.7688 . ? C6 C5 1.400(5) . ? C6 C14 1.483(6) . ? C5 C4 1.385(8) . ? C5 H5A 0.9300 . ? C4 C3 1.407(7) . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? C7 N1 1.505(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.467(5) . ? C8 C9 1.491(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.498(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.505(7) . ? C12 C11 1.523(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? N1 H1 0.8742 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O1W H1W 0.9600 . ? O1W H2W 0.9601 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N3 82.25(16) . . ? C1 Cu1 N1 81.64(17) . . ? N3 Cu1 N1 152.64(17) . . ? C1 Cu1 N2 170.06(15) . . ? N3 Cu1 N2 95.37(15) . . ? N1 Cu1 N2 96.70(15) . . ? C1 Cu1 Cl1 94.27(12) . . ? N3 Cu1 Cl1 104.64(13) . . ? N1 Cu1 Cl1 98.49(13) . . ? N2 Cu1 Cl1 95.68(10) . . ? C1 C2 C3 117.0(4) . . ? C1 C2 C7 114.8(3) . . ? C3 C2 C7 128.1(4) . . ? C6 C1 C2 125.4(3) . . ? C6 C1 Cu1 117.7(3) . . ? C2 C1 Cu1 116.9(3) . . ? C10 N2 C11 109.2(3) . . ? C10 N2 Cu1 115.7(3) . . ? C11 N2 Cu1 113.7(3) . . ? C10 N2 H2 105.7 . . ? C11 N2 H2 105.8 . . ? Cu1 N2 H2 105.8 . . ? C13 N3 C14 110.0(4) . . ? C13 N3 Cu1 115.7(3) . . ? C14 N3 Cu1 113.2(3) . . ? C13 N3 H3 105.7 . . ? C14 N3 H3 105.7 . . ? Cu1 N3 H3 105.7 . . ? C1 C6 C5 117.0(4) . . ? C1 C6 C14 115.4(3) . . ? C5 C6 C14 127.4(4) . . ? C4 C5 C6 119.9(4) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C5 C4 C3 121.3(4) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C2 C7 N1 105.9(3) . . ? C2 C7 H7A 110.6 . . ? N1 C7 H7A 110.6 . . ? C2 C7 H7B 110.6 . . ? N1 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? N1 C8 C9 112.4(4) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 114.0(4) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.6 . . ? N2 C10 C9 113.5(4) . . ? N2 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? N2 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C13 C12 C11 113.7(4) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? N3 C13 C12 112.0(4) . . ? N3 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? N3 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C6 C14 N3 106.9(3) . . ? C6 C14 H14A 110.3 . . ? N3 C14 H14A 110.3 . . ? C6 C14 H14B 110.3 . . ? N3 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? C8 N1 C7 110.6(4) . . ? C8 N1 Cu1 116.9(3) . . ? C7 N1 Cu1 110.5(3) . . ? C8 N1 H1 106.0 . . ? C7 N1 H1 106.0 . . ? Cu1 N1 H1 106.0 . . ? N2 C11 C12 113.0(4) . . ? N2 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N2 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? H1W O1W H2W 95.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 C6 -0.9(6) . . . . ? C7 C2 C1 C6 -177.7(4) . . . . ? C3 C2 C1 Cu1 179.1(3) . . . . ? C7 C2 C1 Cu1 2.3(5) . . . . ? N3 Cu1 C1 C6 -7.9(3) . . . . ? N1 Cu1 C1 C6 -165.7(3) . . . . ? N2 Cu1 C1 C6 -84.6(12) . . . . ? Cl1 Cu1 C1 C6 96.3(3) . . . . ? N3 Cu1 C1 C2 172.1(3) . . . . ? N1 Cu1 C1 C2 14.3(3) . . . . ? N2 Cu1 C1 C2 95.4(12) . . . . ? Cl1 Cu1 C1 C2 -83.6(3) . . . . ? C1 Cu1 N2 C10 -113.8(11) . . . . ? N3 Cu1 N2 C10 170.6(3) . . . . ? N1 Cu1 N2 C10 -34.0(3) . . . . ? Cl1 Cu1 N2 C10 65.3(3) . . . . ? C1 Cu1 N2 C11 118.6(11) . . . . ? N3 Cu1 N2 C11 42.9(3) . . . . ? N1 Cu1 N2 C11 -161.7(3) . . . . ? Cl1 Cu1 N2 C11 -62.4(3) . . . . ? C1 Cu1 N3 C13 146.0(3) . . . . ? N1 Cu1 N3 C13 -159.6(3) . . . . ? N2 Cu1 N3 C13 -43.8(3) . . . . ? Cl1 Cu1 N3 C13 53.5(3) . . . . ? C1 Cu1 N3 C14 17.7(3) . . . . ? N1 Cu1 N3 C14 72.1(5) . . . . ? N2 Cu1 N3 C14 -172.0(3) . . . . ? Cl1 Cu1 N3 C14 -74.7(3) . . . . ? C2 C1 C6 C5 1.0(6) . . . . ? Cu1 C1 C6 C5 -179.0(3) . . . . ? C2 C1 C6 C14 176.1(4) . . . . ? Cu1 C1 C6 C14 -3.8(5) . . . . ? C1 C6 C5 C4 -0.8(6) . . . . ? C14 C6 C5 C4 -175.3(5) . . . . ? C6 C5 C4 C3 0.6(7) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C7 C2 C3 C4 176.9(4) . . . . ? C5 C4 C3 C2 -0.6(7) . . . . ? C1 C2 C7 N1 -23.5(5) . . . . ? C3 C2 C7 N1 160.1(4) . . . . ? N1 C8 C9 C10 70.5(5) . . . . ? C11 N2 C10 C9 -177.0(4) . . . . ? Cu1 N2 C10 C9 53.2(4) . . . . ? C8 C9 C10 N2 -70.6(5) . . . . ? C14 N3 C13 C12 -171.2(4) . . . . ? Cu1 N3 C13 C12 59.0(5) . . . . ? C11 C12 C13 N3 -68.1(6) . . . . ? C1 C6 C14 N3 17.2(6) . . . . ? C5 C6 C14 N3 -168.2(4) . . . . ? C13 N3 C14 C6 -154.2(4) . . . . ? Cu1 N3 C14 C6 -23.0(5) . . . . ? C9 C8 N1 C7 178.0(4) . . . . ? C9 C8 N1 Cu1 -54.4(5) . . . . ? C2 C7 N1 C8 164.8(4) . . . . ? C2 C7 N1 Cu1 33.7(4) . . . . ? C1 Cu1 N1 C8 -154.9(3) . . . . ? N3 Cu1 N1 C8 150.6(3) . . . . ? N2 Cu1 N1 C8 35.0(3) . . . . ? Cl1 Cu1 N1 C8 -61.7(3) . . . . ? C1 Cu1 N1 C7 -27.2(3) . . . . ? N3 Cu1 N1 C7 -81.7(4) . . . . ? N2 Cu1 N1 C7 162.7(3) . . . . ? Cl1 Cu1 N1 C7 65.9(3) . . . . ? C10 N2 C11 C12 170.7(4) . . . . ? Cu1 N2 C11 C12 -58.5(4) . . . . ? C13 C12 C11 N2 69.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.334 _refine_diff_density_min -1.742 _refine_diff_density_rms 0.111 # Attachment '- 1I_acml3p101_last.cif' # Attachment '- 2I_acml2p132b.cif' data_acml2p132b _database_code_depnum_ccdc_archive 'CCDC 735512' #TrackingRef '- 2I_acml2p132b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 Cu I N3, I' _chemical_formula_sum 'C14 H22 Cu I2 N3' _chemical_formula_weight 549.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 15.441(7) _cell_length_b 16.225(7) _cell_length_c 16.686(8) _cell_angle_alpha 66.117(7) _cell_angle_beta 83.242(8) _cell_angle_gamma 70.542(8) _cell_volume 3603(3) _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 yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.026 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 4.634 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.695204 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.1 BRUKER' _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 ccd _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55714 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.34 _reflns_number_total 17207 _reflns_number_gt 10543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0674P)^2^+9.5166P] 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 17207 _refine_ls_number_parameters 721 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 I1 I 0.59660(4) 0.55921(4) 0.06528(3) 0.05027(14) Uani 1 1 d . . . Cu1 Cu 0.71913(6) 0.38642(6) 0.17473(6) 0.0406(2) Uani 1 1 d . . . N1 N 0.8432(4) 0.3961(4) 0.1326(4) 0.0450(15) Uani 1 1 d . . . H1A H 0.8842 0.3435 0.1706 0.054 Uiso 1 1 d R . . C1 C 0.7347(5) 0.3299(5) 0.0912(5) 0.0426(18) Uani 1 1 d . . . N2 N 0.7198(4) 0.4239(5) 0.2747(4) 0.0485(16) Uani 1 1 d . . . H2A H 0.7586 0.3723 0.3159 0.058 Uiso 1 1 d R . . C2 C 0.8093(6) 0.3329(5) 0.0380(5) 0.049(2) Uani 1 1 d . . . N3 N 0.6313(4) 0.3131(4) 0.2239(4) 0.0448(15) Uani 1 1 d . . . H3B H 0.6652 0.2545 0.2608 0.054 Uiso 1 1 d R . . C3 C 0.8223(6) 0.2846(6) -0.0188(6) 0.060(2) Uani 1 1 d . . . H3A H 0.8725 0.2827 -0.0555 0.073 Uiso 1 1 calc R . . C4 C 0.7606(7) 0.2405(6) -0.0197(5) 0.056(2) Uani 1 1 d . . . H4A H 0.7698 0.2096 -0.0578 0.068 Uiso 1 1 calc R . . C5 C 0.6867(7) 0.2404(6) 0.0331(6) 0.061(2) Uani 1 1 d . . . H5A H 0.6466 0.2092 0.0313 0.073 Uiso 1 1 calc R . . C6 C 0.6708(6) 0.2880(5) 0.0913(5) 0.0481(19) Uani 1 1 d . . . C7 C 0.8628(6) 0.3899(6) 0.0442(5) 0.054(2) Uani 1 1 d . . . H7A H 0.8445 0.4528 -0.0023 0.065 Uiso 1 1 calc R . . H7B H 0.9279 0.3597 0.0392 0.065 Uiso 1 1 calc R . . C8 C 0.8651(6) 0.4791(6) 0.1339(6) 0.060(2) Uani 1 1 d . . . H8A H 0.8229 0.5375 0.0944 0.072 Uiso 1 1 calc R . . H8B H 0.9268 0.4766 0.1126 0.072 Uiso 1 1 calc R . . C9 C 0.8585(7) 0.4802(7) 0.2242(7) 0.072(3) Uani 1 1 d . . . H9A H 0.8843 0.5273 0.2239 0.086 Uiso 1 1 calc R . . H9B H 0.8947 0.4187 0.2652 0.086 Uiso 1 1 calc R . . C10 C 0.7574(7) 0.5034(6) 0.2558(6) 0.063(2) Uani 1 1 d . . . H10A H 0.7550 0.5157 0.3084 0.076 Uiso 1 1 calc R . . H10B H 0.7194 0.5604 0.2110 0.076 Uiso 1 1 calc R . . C11 C 0.6315(6) 0.4427(6) 0.3181(6) 0.061(2) Uani 1 1 d . . . H11A H 0.5879 0.4987 0.2774 0.074 Uiso 1 1 calc R . . H11B H 0.6394 0.4565 0.3677 0.074 Uiso 1 1 calc R . . C12 C 0.5919(6) 0.3624(7) 0.3499(6) 0.062(2) Uani 1 1 d . . . H12A H 0.5430 0.3736 0.3901 0.074 Uiso 1 1 calc R . . H12B H 0.6393 0.3042 0.3826 0.074 Uiso 1 1 calc R . . C13 C 0.5535(6) 0.3476(6) 0.2779(6) 0.056(2) Uani 1 1 d . . . H13A H 0.5210 0.3013 0.3042 0.067 Uiso 1 1 calc R . . H13B H 0.5104 0.4069 0.2406 0.067 Uiso 1 1 calc R . . C14 C 0.5934(6) 0.2972(6) 0.1536(5) 0.052(2) Uani 1 1 d . . . H14A H 0.5758 0.2398 0.1786 0.063 Uiso 1 1 calc R . . H14B H 0.5402 0.3505 0.1242 0.063 Uiso 1 1 calc R . . N1B N 0.6744(4) 0.3233(4) 0.7267(4) 0.0409(14) Uani 1 1 d . . . H1BA H 0.7079 0.2670 0.7673 0.049 Uiso 1 1 d R . . I1B I 0.64650(4) 0.54348(4) 0.52058(4) 0.05715(16) Uani 1 1 d . . . Cu1B Cu 0.76639(6) 0.38134(6) 0.65300(6) 0.0363(2) Uani 1 1 d . . . C1B C 0.7448(5) 0.4432(5) 0.7331(5) 0.0389(17) Uani 1 1 d . . . N2B N 0.8014(4) 0.3009(4) 0.5826(4) 0.0469(16) Uani 1 1 d . . . H2BA H 0.8403 0.2446 0.6184 0.056 Uiso 1 1 d R . . C2B C 0.6731(5) 0.4324(5) 0.7902(5) 0.0422(18) Uani 1 1 d . . . N3B N 0.8819(4) 0.4144(4) 0.6349(4) 0.0439(15) Uani 1 1 d . . . H3BB H 0.9238 0.3627 0.6728 0.053 Uiso 1 1 d R . . C3B C 0.6589(6) 0.4778(6) 0.8489(5) 0.053(2) Uani 1 1 d . . . H3BA H 0.6108 0.4744 0.8881 0.063 Uiso 1 1 calc R . . C4B C 0.7164(7) 0.5274(6) 0.8483(5) 0.061(3) Uani 1 1 d . . . H4BA H 0.7054 0.5582 0.8867 0.073 Uiso 1 1 calc R . . C5B C 0.7887(7) 0.5326(5) 0.7933(6) 0.057(2) Uani 1 1 d . . . H5BA H 0.8275 0.5647 0.7962 0.068 Uiso 1 1 calc R . . C6B C 0.8055(6) 0.4895(6) 0.7316(5) 0.0492(19) Uani 1 1 d . . . C7B C 0.6182(6) 0.3790(6) 0.7783(5) 0.0491(19) Uani 1 1 d . . . H7BA H 0.5611 0.4224 0.7471 0.059 Uiso 1 1 calc R . . H7BB H 0.6036 0.3366 0.8348 0.059 Uiso 1 1 calc R . . C8B C 0.6165(6) 0.2985(6) 0.6807(6) 0.050(2) Uani 1 1 d . . . H8BA H 0.5800 0.3560 0.6352 0.060 Uiso 1 1 calc R . . H8BB H 0.5747 0.2701 0.7220 0.060 Uiso 1 1 calc R . . C9B C 0.6732(7) 0.2307(6) 0.6403(6) 0.064(2) Uani 1 1 d . . . H9BA H 0.6333 0.2047 0.6238 0.077 Uiso 1 1 calc R . . H9BB H 0.7171 0.1784 0.6839 0.077 Uiso 1 1 calc R . . C10B C 0.7244(6) 0.2753(6) 0.5609(6) 0.056(2) Uani 1 1 d . . . H10C H 0.6816 0.3323 0.5203 0.067 Uiso 1 1 calc R . . H10D H 0.7495 0.2316 0.5318 0.067 Uiso 1 1 calc R . . C11B C 0.8560(6) 0.3348(7) 0.5020(6) 0.061(2) Uani 1 1 d . . . H11C H 0.8740 0.2880 0.4759 0.073 Uiso 1 1 calc R . . H11D H 0.8170 0.3934 0.4597 0.073 Uiso 1 1 calc R . . C12B C 0.9395(7) 0.3512(7) 0.5194(6) 0.069(3) Uani 1 1 d . . . H12C H 0.9755 0.3628 0.4666 0.083 Uiso 1 1 calc R . . H12H H 0.9762 0.2936 0.5646 0.083 Uiso 1 1 calc R . . C13B C 0.9233(6) 0.4312(6) 0.5473(6) 0.058(2) Uani 1 1 d . . . H13C H 0.9813 0.4419 0.5480 0.070 Uiso 1 1 calc R . . H13D H 0.8829 0.4883 0.5045 0.070 Uiso 1 1 calc R . . C14B C 0.8739(6) 0.4941(6) 0.6624(6) 0.056(2) Uani 1 1 d . . . H14C H 0.9327 0.4866 0.6844 0.067 Uiso 1 1 calc R . . H14D H 0.8543 0.5547 0.6131 0.067 Uiso 1 1 calc R . . I3 I 0.92054(4) 0.16631(4) 0.79162(4) 0.05209(15) Uani 1 1 d . . . I1A I 0.87773(4) 0.68985(4) 0.88012(4) 0.05151(15) Uani 1 1 d . . . C1A C 0.7652(5) 0.9289(5) 0.7479(5) 0.0398(17) Uani 1 1 d . . . Cu1A Cu 0.78030(6) 0.87480(6) 0.87240(6) 0.0363(2) Uani 1 1 d . . . N1A N 0.6508(4) 0.8775(4) 0.8656(5) 0.0474(16) Uani 1 1 d . . . H1AA H 0.6153 0.9360 0.8632 0.057 Uiso 1 1 d R . . N2A N 0.7837(5) 0.8416(4) 1.0015(4) 0.0470(16) Uani 1 1 d . . . H2AA H 0.7532 0.8971 1.0079 0.056 Uiso 1 1 d R . . C2A C 0.6871(6) 0.9299(5) 0.7148(6) 0.051(2) Uani 1 1 d . . . N3A N 0.8787(4) 0.9367(4) 0.8417(4) 0.0368(13) Uani 1 1 d . . . H3AB H 0.8514 0.9959 0.8414 0.044 Uiso 1 1 d R . . C3A C 0.6720(7) 0.9778(6) 0.6238(6) 0.066(3) Uani 1 1 d . . . H3AA H 0.6201 0.9817 0.5976 0.079 Uiso 1 1 calc R . . C4A C 0.7363(8) 1.0195(6) 0.5736(6) 0.072(3) Uani 1 1 d . . . H4AA H 0.7257 1.0516 0.5134 0.087 Uiso 1 1 calc R . . C5A C 0.8141(7) 1.0157(6) 0.6080(6) 0.063(3) Uani 1 1 d . . . H5AA H 0.8556 1.0436 0.5718 0.075 Uiso 1 1 calc R . . C6A C 0.8306(6) 0.9686(5) 0.6995(5) 0.0454(19) Uani 1 1 d . . . C7A C 0.6327(6) 0.8753(6) 0.7818(6) 0.055(2) Uani 1 1 d . . . H7AA H 0.5677 0.9042 0.7665 0.067 Uiso 1 1 calc R . . H7AB H 0.6516 0.8104 0.7859 0.067 Uiso 1 1 calc R . . C8A C 0.6167(7) 0.8098(7) 0.9409(7) 0.068(3) Uani 1 1 d . . . H8AA H 0.6457 0.7466 0.9414 0.081 Uiso 1 1 calc R . . H8AB H 0.5511 0.8255 0.9329 0.081 Uiso 1 1 calc R . . C9A C 0.6341(8) 0.8082(7) 1.0282(7) 0.075(3) Uani 1 1 d . . . H9AA H 0.6060 0.8719 1.0270 0.090 Uiso 1 1 calc R . . H9AB H 0.6034 0.7675 1.0727 0.090 Uiso 1 1 calc R . . C10A C 0.7320(7) 0.7753(6) 1.0552(6) 0.062(2) Uani 1 1 d . . . H10E H 0.7618 0.7142 1.0513 0.075 Uiso 1 1 calc R . . H10F H 0.7351 0.7663 1.1160 0.075 Uiso 1 1 calc R . . C11A C 0.8783(6) 0.8114(6) 1.0400(5) 0.059(2) Uani 1 1 d . . . H11E H 0.8732 0.7997 1.1019 0.071 Uiso 1 1 calc R . . H11F H 0.9150 0.7524 1.0348 0.071 Uiso 1 1 calc R . . C12A C 0.9258(7) 0.8835(6) 0.9964(6) 0.063(2) Uani 1 1 d . . . H12D H 0.9786 0.8679 1.0322 0.075 Uiso 1 1 calc R . . H12E H 0.8844 0.9448 0.9931 0.075 Uiso 1 1 calc R . . C13A C 0.9580(5) 0.8917(6) 0.9046(6) 0.055(2) Uani 1 1 d . . . H13E H 0.9994 0.9295 0.8853 0.065 Uiso 1 1 calc R . . H13F H 0.9915 0.8290 0.9056 0.065 Uiso 1 1 calc R . . C14A C 0.9116(6) 0.9509(6) 0.7508(5) 0.0487(19) Uani 1 1 d . . . H14E H 0.9348 1.0046 0.7266 0.058 Uiso 1 1 calc R . . H14F H 0.9602 0.8948 0.7505 0.058 Uiso 1 1 calc R . . I2 I 0.13497(4) 0.81562(4) 0.65662(4) 0.05819(16) Uani 1 1 d . . . I4 I 0.64016(4) 1.08841(4) 0.90222(4) 0.05794(16) Uani 1 1 d . . . I5 I 0.85499(4) 0.68094(4) 0.31600(4) 0.06151(17) Uani 1 1 d . . . Cu1C Cu 0.72300(6) 0.88309(6) 0.35871(6) 0.0388(2) Uani 1 1 d . . . N1C N 0.8363(5) 0.9169(5) 0.3147(5) 0.0564(18) Uani 1 1 d . . . H1CA H 0.8736 0.8661 0.3034 0.068 Uiso 1 1 d R . . C1C C 0.7809(6) 0.8418(5) 0.4691(5) 0.0461(19) Uani 1 1 d . . . N2C N 0.6774(6) 0.9070(6) 0.2422(5) 0.071(2) Uani 1 1 d . . . H2CA H 0.7137 0.8555 0.2316 0.085 Uiso 1 1 d R . . C2C C 0.8607(6) 0.8613(7) 0.4676(7) 0.061(3) Uani 1 1 d . . . N3C N 0.6520(5) 0.7997(5) 0.4314(6) 0.065(2) Uani 1 1 d . . . H3CB H 0.6855 0.7419 0.4311 0.078 Uiso 1 1 d R . . C3C C 0.9057(8) 0.8269(9) 0.5476(10) 0.099(5) Uani 1 1 d . . . H3CA H 0.9604 0.8384 0.5496 0.119 Uiso 1 1 calc R . . I1C I 0.59812(4) 1.06237(4) 0.36386(4) 0.05438(15) Uani 1 1 d . . . C4C C 0.8711(14) 0.7775(12) 0.6214(11) 0.138(9) Uani 1 1 d . . . H4CA H 0.9020 0.7557 0.6742 0.166 Uiso 1 1 calc R . . C5C C 0.7915(13) 0.7580(8) 0.6217(7) 0.110(6) Uani 1 1 d . . . H5CA H 0.7694 0.7225 0.6741 0.132 Uiso 1 1 calc R . . C6C C 0.7426(9) 0.7920(6) 0.5418(6) 0.075(3) Uani 1 1 d . . . C7C C 0.8877(7) 0.9197(7) 0.3831(8) 0.073(3) Uani 1 1 d . . . H7CA H 0.9533 0.8953 0.3760 0.088 Uiso 1 1 calc R . . H7CB H 0.8728 0.9844 0.3786 0.088 Uiso 1 1 calc R . . C8C C 0.8277(8) 0.9981(6) 0.2294(7) 0.080(3) Uani 1 1 d . . . H8CA H 0.7871 1.0553 0.2358 0.096 Uiso 1 1 calc R . . H8CB H 0.8875 1.0066 0.2135 0.096 Uiso 1 1 calc R . . C9C C 0.7918(11) 0.9863(8) 0.1581(7) 0.117(6) Uani 1 1 d . . . H9CA H 0.7979 1.0365 0.1031 0.141 Uiso 1 1 calc R . . H9CB H 0.8297 0.9264 0.1553 0.141 Uiso 1 1 calc R . . C10C C 0.6954(9) 0.9879(7) 0.1667(6) 0.089(4) Uani 1 1 d . . . H10G H 0.6760 0.9884 0.1132 0.107 Uiso 1 1 calc R . . H10H H 0.6579 1.0465 0.1723 0.107 Uiso 1 1 calc R . . C11C C 0.5847(8) 0.9049(9) 0.2360(9) 0.100(5) Uani 1 1 d . . . H11G H 0.5766 0.9055 0.1789 0.120 Uiso 1 1 calc R . . H11H H 0.5410 0.9623 0.2393 0.120 Uiso 1 1 calc R . . C12C C 0.5628(9) 0.8213(10) 0.3048(14) 0.136(7) Uani 1 1 d . . . H12F H 0.6081 0.7639 0.3030 0.163 Uiso 1 1 calc R . . H12G H 0.5034 0.8219 0.2908 0.163 Uiso 1 1 calc R . . C13C C 0.5609(7) 0.8173(8) 0.3974(11) 0.097(4) Uani 1 1 d . . . H13G H 0.5198 0.8769 0.3984 0.116 Uiso 1 1 calc R . . H13H H 0.5363 0.7673 0.4358 0.116 Uiso 1 1 calc R . . C14C C 0.6523(9) 0.7846(7) 0.5244(8) 0.090(4) Uani 1 1 d . . . H14G H 0.6473 0.7224 0.5614 0.108 Uiso 1 1 calc R . . H14H H 0.6013 0.8324 0.5362 0.108 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 I1 0.0553(3) 0.0369(3) 0.0466(3) -0.0105(2) -0.0047(2) -0.0052(2) Cu1 0.0471(5) 0.0344(4) 0.0398(5) -0.0189(4) -0.0051(4) -0.0045(4) N1 0.047(4) 0.032(3) 0.051(4) -0.019(3) -0.009(3) 0.000(3) C1 0.054(5) 0.033(4) 0.038(4) -0.020(3) -0.006(3) 0.000(3) N2 0.053(4) 0.042(4) 0.048(4) -0.022(3) -0.010(3) -0.002(3) C2 0.058(5) 0.039(4) 0.036(4) -0.010(3) -0.009(4) -0.002(4) N3 0.053(4) 0.035(3) 0.038(3) -0.012(3) -0.004(3) -0.004(3) C3 0.065(6) 0.053(5) 0.051(5) -0.029(4) -0.006(4) 0.010(5) C4 0.074(6) 0.045(5) 0.045(5) -0.029(4) -0.006(4) 0.004(4) C5 0.089(7) 0.040(4) 0.054(5) -0.013(4) -0.022(5) -0.020(5) C6 0.066(5) 0.031(4) 0.044(4) -0.013(3) -0.011(4) -0.011(4) C7 0.043(4) 0.065(6) 0.052(5) -0.025(4) -0.002(4) -0.011(4) C8 0.054(5) 0.050(5) 0.077(6) -0.028(5) 0.004(5) -0.015(4) C9 0.075(7) 0.066(6) 0.094(8) -0.049(6) -0.021(6) -0.017(5) C10 0.082(7) 0.053(5) 0.065(6) -0.034(5) -0.009(5) -0.017(5) C11 0.072(6) 0.060(6) 0.044(5) -0.028(4) -0.006(4) 0.002(5) C12 0.064(6) 0.064(6) 0.049(5) -0.028(5) 0.007(4) -0.003(5) C13 0.049(5) 0.048(5) 0.053(5) -0.014(4) 0.008(4) -0.003(4) C14 0.059(5) 0.047(5) 0.049(5) -0.014(4) -0.004(4) -0.020(4) N1B 0.044(3) 0.039(3) 0.042(3) -0.019(3) 0.001(3) -0.012(3) I1B 0.0653(4) 0.0424(3) 0.0536(3) -0.0159(3) -0.0033(3) -0.0066(3) Cu1B 0.0408(5) 0.0335(4) 0.0375(5) -0.0167(4) 0.0034(4) -0.0125(4) C1B 0.049(4) 0.026(3) 0.040(4) -0.014(3) -0.009(3) -0.006(3) N2B 0.055(4) 0.040(3) 0.043(4) -0.020(3) 0.002(3) -0.007(3) C2B 0.046(4) 0.035(4) 0.040(4) -0.019(3) 0.000(3) -0.001(3) N3B 0.049(4) 0.039(3) 0.042(3) -0.012(3) 0.006(3) -0.019(3) C3B 0.068(6) 0.044(4) 0.035(4) -0.017(4) 0.000(4) -0.002(4) C4B 0.108(8) 0.042(5) 0.041(5) -0.026(4) -0.013(5) -0.016(5) C5B 0.083(6) 0.037(4) 0.064(6) -0.024(4) -0.020(5) -0.021(4) C6B 0.052(5) 0.041(4) 0.054(5) -0.020(4) -0.002(4) -0.012(4) C7B 0.053(5) 0.044(4) 0.051(5) -0.022(4) 0.009(4) -0.013(4) C8B 0.055(5) 0.058(5) 0.052(5) -0.026(4) 0.005(4) -0.031(4) C9B 0.082(7) 0.054(5) 0.073(6) -0.037(5) -0.005(5) -0.025(5) C10B 0.074(6) 0.051(5) 0.059(5) -0.032(4) -0.005(5) -0.023(4) C11B 0.072(6) 0.073(6) 0.045(5) -0.033(5) 0.014(4) -0.024(5) C12B 0.064(6) 0.082(7) 0.053(5) -0.030(5) 0.020(5) -0.014(5) C13B 0.052(5) 0.055(5) 0.058(5) -0.013(4) 0.011(4) -0.020(4) C14B 0.054(5) 0.046(5) 0.075(6) -0.025(4) 0.005(4) -0.027(4) I3 0.0596(3) 0.0450(3) 0.0492(3) -0.0168(2) -0.0047(3) -0.0135(3) I1A 0.0575(3) 0.0387(3) 0.0603(3) -0.0264(2) -0.0087(3) -0.0053(2) C1A 0.052(4) 0.032(4) 0.037(4) -0.016(3) -0.005(3) -0.008(3) Cu1A 0.0390(5) 0.0329(4) 0.0371(5) -0.0141(4) -0.0022(4) -0.0096(4) N1A 0.038(3) 0.035(3) 0.069(4) -0.021(3) -0.002(3) -0.009(3) N2A 0.061(4) 0.038(3) 0.041(4) -0.017(3) 0.005(3) -0.013(3) C2A 0.055(5) 0.036(4) 0.058(5) -0.021(4) -0.021(4) 0.000(4) N3A 0.038(3) 0.034(3) 0.041(3) -0.015(3) -0.001(3) -0.013(3) C3A 0.084(7) 0.049(5) 0.058(6) -0.031(5) -0.032(5) 0.012(5) C4A 0.119(9) 0.045(5) 0.038(5) -0.019(4) -0.024(6) 0.005(6) C5A 0.097(7) 0.042(5) 0.043(5) -0.017(4) 0.002(5) -0.014(5) C6A 0.062(5) 0.035(4) 0.042(4) -0.023(3) -0.002(4) -0.009(4) C7A 0.049(5) 0.049(5) 0.071(6) -0.025(4) -0.019(4) -0.010(4) C8A 0.062(6) 0.061(6) 0.096(8) -0.037(6) 0.021(5) -0.037(5) C9A 0.089(8) 0.066(6) 0.081(7) -0.033(6) 0.051(6) -0.048(6) C10A 0.091(7) 0.053(5) 0.040(5) -0.016(4) 0.019(5) -0.029(5) C11A 0.082(6) 0.052(5) 0.041(5) -0.018(4) -0.011(4) -0.015(5) C12A 0.075(6) 0.055(5) 0.056(5) -0.020(4) -0.025(5) -0.011(5) C13A 0.041(4) 0.060(5) 0.065(5) -0.027(5) -0.013(4) -0.011(4) C14A 0.054(5) 0.052(5) 0.051(5) -0.029(4) 0.018(4) -0.025(4) I2 0.0604(4) 0.0415(3) 0.0644(4) -0.0218(3) -0.0043(3) -0.0027(3) I4 0.0704(4) 0.0412(3) 0.0599(3) -0.0207(3) -0.0065(3) -0.0110(3) I5 0.0665(4) 0.0476(3) 0.0644(4) -0.0178(3) -0.0078(3) -0.0126(3) Cu1C 0.0427(5) 0.0336(4) 0.0413(5) -0.0148(4) -0.0028(4) -0.0120(4) N1C 0.058(4) 0.048(4) 0.058(4) -0.018(3) 0.012(4) -0.017(3) C1C 0.064(5) 0.035(4) 0.036(4) -0.020(3) -0.007(4) -0.002(4) N2C 0.076(5) 0.056(5) 0.071(5) -0.030(4) -0.033(4) 0.010(4) C2C 0.051(5) 0.065(6) 0.078(6) -0.054(5) -0.022(5) 0.007(4) N3C 0.049(4) 0.049(4) 0.092(6) -0.021(4) 0.007(4) -0.019(4) C3C 0.087(8) 0.089(9) 0.119(10) -0.077(9) -0.061(8) 0.043(7) I1C 0.0571(3) 0.0483(3) 0.0543(3) -0.0177(3) -0.0058(3) -0.0129(3) C4C 0.199(19) 0.096(11) 0.090(11) -0.071(10) -0.079(13) 0.059(12) C5C 0.209(17) 0.041(6) 0.036(6) -0.010(4) 0.001(8) 0.008(8) C6C 0.137(10) 0.027(4) 0.047(5) -0.016(4) 0.014(6) -0.010(5) C7C 0.061(6) 0.072(7) 0.117(9) -0.058(7) -0.002(6) -0.031(5) C8C 0.092(8) 0.045(5) 0.088(8) -0.020(5) 0.052(6) -0.026(5) C9C 0.171(15) 0.065(7) 0.051(7) -0.012(6) 0.020(8) 0.022(8) C10C 0.124(10) 0.062(6) 0.046(6) -0.027(5) -0.019(6) 0.027(7) C11C 0.102(9) 0.080(8) 0.136(11) -0.068(8) -0.062(8) 0.004(7) C12C 0.076(9) 0.085(10) 0.25(2) -0.062(13) -0.070(11) -0.014(7) C13C 0.046(6) 0.063(7) 0.180(14) -0.044(8) 0.013(7) -0.024(5) C14C 0.133(11) 0.056(6) 0.087(8) -0.035(6) 0.064(8) -0.051(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 I1 Cu1 2.8122(13) . ? Cu1 C1 1.911(7) . ? Cu1 N3 1.988(7) . ? Cu1 N2 1.996(6) . ? Cu1 N1 1.997(7) . ? N1 C8 1.502(10) . ? N1 C7 1.507(10) . ? C1 C2 1.371(11) . ? C1 C6 1.371(11) . ? N2 C11 1.465(11) . ? N2 C10 1.492(11) . ? C2 C3 1.417(11) . ? C2 C7 1.467(12) . ? N3 C13 1.508(10) . ? N3 C14 1.514(10) . ? C3 C4 1.372(13) . ? C4 C5 1.358(13) . ? C5 C6 1.424(11) . ? C6 C14 1.499(12) . ? C8 C9 1.506(13) . ? C9 C10 1.560(14) . ? C11 C12 1.499(13) . ? C12 C13 1.533(12) . ? N1B C8B 1.484(9) . ? N1B C7B 1.497(9) . ? N1B Cu1B 1.990(6) . ? I1B Cu1B 2.8707(13) . ? Cu1B C1B 1.914(7) . ? Cu1B N3B 1.985(6) . ? Cu1B N2B 1.999(6) . ? C1B C6B 1.375(11) . ? C1B C2B 1.382(11) . ? N2B C11B 1.505(10) . ? N2B C10B 1.505(10) . ? C2B C3B 1.405(10) . ? C2B C7B 1.476(11) . ? N3B C13B 1.481(10) . ? N3B C14B 1.502(10) . ? C3B C4B 1.379(13) . ? C4B C5B 1.362(13) . ? C5B C6B 1.421(11) . ? C6B C14B 1.466(12) . ? C8B C9B 1.500(12) . ? C9B C10B 1.505(13) . ? C11B C12B 1.483(13) . ? C12B C13B 1.486(13) . ? I1A Cu1A 2.8301(15) . ? C1A C2A 1.377(10) . ? C1A C6A 1.382(11) . ? C1A Cu1A 1.908(7) . ? Cu1A N3A 1.999(6) . ? Cu1A N2A 2.000(6) . ? Cu1A N1A 2.001(6) . ? N1A C8A 1.475(11) . ? N1A C7A 1.476(10) . ? N2A C10A 1.491(11) . ? N2A C11A 1.509(11) . ? C2A C3A 1.404(12) . ? C2A C7A 1.487(12) . ? N3A C14A 1.491(9) . ? N3A C13A 1.491(9) . ? C3A C4A 1.391(15) . ? C4A C5A 1.364(14) . ? C5A C6A 1.413(11) . ? C6A C14A 1.480(11) . ? C8A C9A 1.502(15) . ? C9A C10A 1.483(14) . ? C11A C12A 1.481(13) . ? C12A C13A 1.520(12) . ? Cu1C C1C 1.907(7) . ? Cu1C N3C 1.961(7) . ? Cu1C N1C 1.977(7) . ? Cu1C N2C 1.988(7) . ? Cu1C I1C 2.9349(15) . ? N1C C8C 1.480(12) . ? N1C C7C 1.488(12) . ? C1C C6C 1.353(13) . ? C1C C2C 1.365(12) . ? N2C C11C 1.459(14) . ? N2C C10C 1.487(14) . ? C2C C3C 1.390(14) . ? C2C C7C 1.449(14) . ? N3C C14C 1.470(14) . ? N3C C13C 1.475(14) . ? C3C C4C 1.33(2) . ? C4C C5C 1.37(2) . ? C5C C6C 1.421(17) . ? C6C C14C 1.508(17) . ? C8C C9C 1.473(18) . ? C9C C10C 1.471(18) . ? C11C C12C 1.492(19) . ? C12C C13C 1.52(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N3 81.6(3) . . ? C1 Cu1 N2 169.7(3) . . ? N3 Cu1 N2 97.4(3) . . ? C1 Cu1 N1 81.5(3) . . ? N3 Cu1 N1 152.1(2) . . ? N2 Cu1 N1 95.2(3) . . ? C1 Cu1 I1 93.4(2) . . ? N3 Cu1 I1 98.90(18) . . ? N2 Cu1 I1 96.81(18) . . ? N1 Cu1 I1 104.22(18) . . ? C8 N1 C7 110.8(7) . . ? C8 N1 Cu1 116.0(5) . . ? C7 N1 Cu1 112.0(5) . . ? C2 C1 C6 125.9(7) . . ? C2 C1 Cu1 117.5(6) . . ? C6 C1 Cu1 116.6(6) . . ? C11 N2 C10 109.1(7) . . ? C11 N2 Cu1 114.7(5) . . ? C10 N2 Cu1 115.7(5) . . ? C1 C2 C3 115.9(8) . . ? C1 C2 C7 115.7(7) . . ? C3 C2 C7 128.4(8) . . ? C13 N3 C14 109.4(6) . . ? C13 N3 Cu1 118.3(5) . . ? C14 N3 Cu1 111.4(5) . . ? C4 C3 C2 119.9(9) . . ? C5 C4 C3 122.4(8) . . ? C4 C5 C6 119.7(9) . . ? C1 C6 C5 116.1(8) . . ? C1 C6 C14 115.9(7) . . ? C5 C6 C14 128.0(8) . . ? C2 C7 N1 106.5(7) . . ? N1 C8 C9 112.4(8) . . ? C8 C9 C10 112.2(8) . . ? N2 C10 C9 111.9(7) . . ? N2 C11 C12 114.1(7) . . ? C11 C12 C13 115.1(8) . . ? N3 C13 C12 109.5(7) . . ? C6 C14 N3 104.5(6) . . ? C8B N1B C7B 112.1(6) . . ? C8B N1B Cu1B 115.4(5) . . ? C7B N1B Cu1B 112.5(5) . . ? C1B Cu1B N3B 81.9(3) . . ? C1B Cu1B N1B 82.1(3) . . ? N3B Cu1B N1B 153.4(3) . . ? C1B Cu1B N2B 171.7(3) . . ? N3B Cu1B N2B 96.1(3) . . ? N1B Cu1B N2B 96.7(3) . . ? C1B Cu1B I1B 93.0(2) . . ? N3B Cu1B I1B 102.06(19) . . ? N1B Cu1B I1B 99.83(18) . . ? N2B Cu1B I1B 95.28(19) . . ? C6B C1B C2B 126.3(7) . . ? C6B C1B Cu1B 116.7(6) . . ? C2B C1B Cu1B 116.9(5) . . ? C11B N2B C10B 110.1(6) . . ? C11B N2B Cu1B 115.5(5) . . ? C10B N2B Cu1B 115.5(5) . . ? C1B C2B C3B 116.0(8) . . ? C1B C2B C7B 115.6(6) . . ? C3B C2B C7B 128.4(8) . . ? C13B N3B C14B 110.9(6) . . ? C13B N3B Cu1B 116.7(5) . . ? C14B N3B Cu1B 112.1(5) . . ? C4B C3B C2B 119.9(8) . . ? C5B C4B C3B 122.0(7) . . ? C4B C5B C6B 120.5(8) . . ? C1B C6B C5B 115.2(8) . . ? C1B C6B C14B 115.9(7) . . ? C5B C6B C14B 128.7(8) . . ? C2B C7B N1B 107.5(6) . . ? N1B C8B C9B 111.9(7) . . ? C8B C9B C10B 113.6(7) . . ? C9B C10B N2B 113.1(7) . . ? C12B C11B N2B 113.7(7) . . ? C11B C12B C13B 115.8(8) . . ? N3B C13B C12B 113.4(7) . . ? C6B C14B N3B 106.6(6) . . ? C2A C1A C6A 125.9(7) . . ? C2A C1A Cu1A 116.9(6) . . ? C6A C1A Cu1A 117.0(5) . . ? C1A Cu1A N3A 81.3(3) . . ? C1A Cu1A N2A 169.7(3) . . ? N3A Cu1A N2A 96.5(3) . . ? C1A Cu1A N1A 81.5(3) . . ? N3A Cu1A N1A 152.2(2) . . ? N2A Cu1A N1A 96.6(3) . . ? C1A Cu1A I1A 94.1(2) . . ? N3A Cu1A I1A 102.25(17) . . ? N2A Cu1A I1A 96.23(18) . . ? N1A Cu1A I1A 100.65(18) . . ? C8A N1A C7A 111.9(7) . . ? C8A N1A Cu1A 117.7(6) . . ? C7A N1A Cu1A 110.7(5) . . ? C10A N2A C11A 111.4(6) . . ? C10A N2A Cu1A 115.0(5) . . ? C11A N2A Cu1A 114.7(5) . . ? C1A C2A C3A 116.6(9) . . ? C1A C2A C7A 114.0(7) . . ? C3A C2A C7A 129.4(8) . . ? C14A N3A C13A 110.5(6) . . ? C14A N3A Cu1A 111.7(4) . . ? C13A N3A Cu1A 116.3(5) . . ? C4A C3A C2A 118.7(9) . . ? C5A C4A C3A 123.4(8) . . ? C4A C5A C6A 119.1(9) . . ? C1A C6A C5A 116.2(8) . . ? C1A C6A C14A 114.8(7) . . ? C5A C6A C14A 128.8(8) . . ? N1A C7A C2A 106.4(6) . . ? N1A C8A C9A 114.3(7) . . ? C10A C9A C8A 115.7(8) . . ? C9A C10A N2A 114.1(7) . . ? C12A C11A N2A 112.5(7) . . ? C11A C12A C13A 114.2(7) . . ? N3A C13A C12A 111.0(7) . . ? C6A C14A N3A 105.7(6) . . ? C1C Cu1C N3C 81.5(4) . . ? C1C Cu1C N1C 81.9(3) . . ? N3C Cu1C N1C 155.2(3) . . ? C1C Cu1C N2C 170.6(3) . . ? N3C Cu1C N2C 97.8(4) . . ? N1C Cu1C N2C 95.6(3) . . ? C1C Cu1C I1C 94.9(2) . . ? N3C Cu1C I1C 98.1(2) . . ? N1C Cu1C I1C 101.5(2) . . ? N2C Cu1C I1C 94.5(2) . . ? C8C N1C C7C 113.9(8) . . ? C8C N1C Cu1C 116.2(6) . . ? C7C N1C Cu1C 113.0(6) . . ? C6C C1C C2C 125.4(9) . . ? C6C C1C Cu1C 117.8(8) . . ? C2C C1C Cu1C 116.7(7) . . ? C11C N2C C10C 110.8(9) . . ? C11C N2C Cu1C 118.1(8) . . ? C10C N2C Cu1C 116.1(7) . . ? C1C C2C C3C 116.9(12) . . ? C1C C2C C7C 116.6(8) . . ? C3C C2C C7C 126.5(11) . . ? C14C N3C C13C 113.5(10) . . ? C14C N3C Cu1C 113.1(7) . . ? C13C N3C Cu1C 117.2(7) . . ? C4C C3C C2C 120.5(14) . . ? C3C C4C C5C 122.0(13) . . ? C4C C5C C6C 119.8(13) . . ? C1C C6C C5C 115.5(13) . . ? C1C C6C C14C 114.0(9) . . ? C5C C6C C14C 130.5(12) . . ? C2C C7C N1C 107.3(7) . . ? C9C C8C N1C 113.4(9) . . ? C10C C9C C8C 115.0(10) . . ? C9C C10C N2C 114.9(9) . . ? N2C C11C C12C 114.8(9) . . ? C11C C12C C13C 114.9(11) . . ? N3C C13C C12C 113.3(10) . . ? N3C C14C C6C 106.0(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Cu1 N1 C8 149.1(6) . . . . ? N3 Cu1 N1 C8 -157.4(6) . . . . ? N2 Cu1 N1 C8 -40.8(6) . . . . ? I1 Cu1 N1 C8 57.6(6) . . . . ? C1 Cu1 N1 C7 20.4(5) . . . . ? N3 Cu1 N1 C7 73.9(8) . . . . ? N2 Cu1 N1 C7 -169.4(5) . . . . ? I1 Cu1 N1 C7 -71.0(5) . . . . ? N3 Cu1 C1 C2 -165.4(6) . . . . ? N2 Cu1 C1 C2 -80(2) . . . . ? N1 Cu1 C1 C2 -7.8(6) . . . . ? I1 Cu1 C1 C2 96.1(6) . . . . ? N3 Cu1 C1 C6 13.3(6) . . . . ? N2 Cu1 C1 C6 98.8(19) . . . . ? N1 Cu1 C1 C6 170.9(6) . . . . ? I1 Cu1 C1 C6 -85.2(6) . . . . ? C1 Cu1 N2 C11 -119.2(18) . . . . ? N3 Cu1 N2 C11 -35.1(6) . . . . ? N1 Cu1 N2 C11 169.9(6) . . . . ? I1 Cu1 N2 C11 64.8(6) . . . . ? C1 Cu1 N2 C10 112.4(18) . . . . ? N3 Cu1 N2 C10 -163.5(6) . . . . ? N1 Cu1 N2 C10 41.5(6) . . . . ? I1 Cu1 N2 C10 -63.5(5) . . . . ? C6 C1 C2 C3 -2.8(11) . . . . ? Cu1 C1 C2 C3 175.7(5) . . . . ? C6 C1 C2 C7 174.3(7) . . . . ? Cu1 C1 C2 C7 -7.2(9) . . . . ? C1 Cu1 N3 C13 -154.8(6) . . . . ? N2 Cu1 N3 C13 35.6(6) . . . . ? N1 Cu1 N3 C13 151.7(6) . . . . ? I1 Cu1 N3 C13 -62.6(5) . . . . ? C1 Cu1 N3 C14 -26.8(5) . . . . ? N2 Cu1 N3 C14 163.5(5) . . . . ? N1 Cu1 N3 C14 -80.3(7) . . . . ? I1 Cu1 N3 C14 65.4(5) . . . . ? C1 C2 C3 C4 1.6(11) . . . . ? C7 C2 C3 C4 -175.1(8) . . . . ? C2 C3 C4 C5 -0.6(13) . . . . ? C3 C4 C5 C6 0.6(13) . . . . ? C2 C1 C6 C5 2.9(11) . . . . ? Cu1 C1 C6 C5 -175.7(5) . . . . ? C2 C1 C6 C14 -177.9(7) . . . . ? Cu1 C1 C6 C14 3.5(9) . . . . ? C4 C5 C6 C1 -1.6(11) . . . . ? C4 C5 C6 C14 179.2(8) . . . . ? C1 C2 C7 N1 22.7(9) . . . . ? C3 C2 C7 N1 -160.6(7) . . . . ? C8 N1 C7 C2 -159.3(6) . . . . ? Cu1 N1 C7 C2 -28.0(7) . . . . ? C7 N1 C8 C9 -172.4(7) . . . . ? Cu1 N1 C8 C9 58.4(8) . . . . ? N1 C8 C9 C10 -69.6(10) . . . . ? C11 N2 C10 C9 170.3(7) . . . . ? Cu1 N2 C10 C9 -58.6(8) . . . . ? C8 C9 C10 N2 70.1(10) . . . . ? C10 N2 C11 C12 -173.3(7) . . . . ? Cu1 N2 C11 C12 55.1(8) . . . . ? N2 C11 C12 C13 -72.7(9) . . . . ? C14 N3 C13 C12 179.2(7) . . . . ? Cu1 N3 C13 C12 -51.9(8) . . . . ? C11 C12 C13 N3 68.2(9) . . . . ? C1 C6 C14 N3 -23.9(9) . . . . ? C5 C6 C14 N3 155.3(8) . . . . ? C13 N3 C14 C6 165.9(6) . . . . ? Cu1 N3 C14 C6 33.3(7) . . . . ? C8B N1B Cu1B C1B 149.7(6) . . . . ? C7B N1B Cu1B C1B 19.4(5) . . . . ? C8B N1B Cu1B N3B -156.9(6) . . . . ? C7B N1B Cu1B N3B 72.8(8) . . . . ? C8B N1B Cu1B N2B -38.6(5) . . . . ? C7B N1B Cu1B N2B -168.9(5) . . . . ? C8B N1B Cu1B I1B 58.0(5) . . . . ? C7B N1B Cu1B I1B -72.3(5) . . . . ? N3B Cu1B C1B C6B 8.7(6) . . . . ? N1B Cu1B C1B C6B 167.4(6) . . . . ? N2B Cu1B C1B C6B 85(2) . . . . ? I1B Cu1B C1B C6B -93.1(6) . . . . ? N3B Cu1B C1B C2B -167.7(6) . . . . ? N1B Cu1B C1B C2B -9.0(5) . . . . ? N2B Cu1B C1B C2B -91(2) . . . . ? I1B Cu1B C1B C2B 90.5(5) . . . . ? C1B Cu1B N2B C11B -112(2) . . . . ? N3B Cu1B N2B C11B -36.7(6) . . . . ? N1B Cu1B N2B C11B 166.6(6) . . . . ? I1B Cu1B N2B C11B 66.0(6) . . . . ? C1B Cu1B N2B C10B 117(2) . . . . ? N3B Cu1B N2B C10B -167.3(5) . . . . ? N1B Cu1B N2B C10B 36.0(6) . . . . ? I1B Cu1B N2B C10B -64.6(5) . . . . ? C6B C1B C2B C3B 3.6(11) . . . . ? Cu1B C1B C2B C3B 179.5(5) . . . . ? C6B C1B C2B C7B -179.7(7) . . . . ? Cu1B C1B C2B C7B -3.7(9) . . . . ? C1B Cu1B N3B C13B -150.4(6) . . . . ? N1B Cu1B N3B C13B 156.1(6) . . . . ? N2B Cu1B N3B C13B 37.6(6) . . . . ? I1B Cu1B N3B C13B -59.1(5) . . . . ? C1B Cu1B N3B C14B -21.0(5) . . . . ? N1B Cu1B N3B C14B -74.4(8) . . . . ? N2B Cu1B N3B C14B 167.1(5) . . . . ? I1B Cu1B N3B C14B 70.3(5) . . . . ? C1B C2B C3B C4B -1.5(11) . . . . ? C7B C2B C3B C4B -177.8(8) . . . . ? C2B C3B C4B C5B -1.3(12) . . . . ? C3B C4B C5B C6B 2.4(13) . . . . ? C2B C1B C6B C5B -2.6(11) . . . . ? Cu1B C1B C6B C5B -178.6(5) . . . . ? C2B C1B C6B C14B -177.9(7) . . . . ? Cu1B C1B C6B C14B 6.1(9) . . . . ? C4B C5B C6B C1B -0.5(12) . . . . ? C4B C5B C6B C14B 174.1(8) . . . . ? C1B C2B C7B N1B 18.7(9) . . . . ? C3B C2B C7B N1B -165.0(7) . . . . ? C8B N1B C7B C2B -157.1(6) . . . . ? Cu1B N1B C7B C2B -25.2(7) . . . . ? C7B N1B C8B C9B -171.4(7) . . . . ? Cu1B N1B C8B C9B 58.2(8) . . . . ? N1B C8B C9B C10B -72.3(10) . . . . ? C8B C9B C10B N2B 69.7(10) . . . . ? C11B N2B C10B C9B 173.6(7) . . . . ? Cu1B N2B C10B C9B -53.2(8) . . . . ? C10B N2B C11B C12B -173.5(7) . . . . ? Cu1B N2B C11B C12B 53.4(9) . . . . ? N2B C11B C12B C13B -67.2(11) . . . . ? C14B N3B C13B C12B 175.6(7) . . . . ? Cu1B N3B C13B C12B -54.3(9) . . . . ? C11B C12B C13B N3B 67.4(11) . . . . ? C1B C6B C14B N3B -22.1(10) . . . . ? C5B C6B C14B N3B 163.3(8) . . . . ? C13B N3B C14B C6B 160.6(7) . . . . ? Cu1B N3B C14B C6B 28.1(8) . . . . ? C2A C1A Cu1A N3A -167.6(6) . . . . ? C6A C1A Cu1A N3A 8.6(5) . . . . ? C2A C1A Cu1A N2A -89.3(18) . . . . ? C6A C1A Cu1A N2A 87.0(18) . . . . ? C2A C1A Cu1A N1A -9.6(5) . . . . ? C6A C1A Cu1A N1A 166.7(6) . . . . ? C2A C1A Cu1A I1A 90.6(5) . . . . ? C6A C1A Cu1A I1A -93.2(5) . . . . ? C1A Cu1A N1A C8A 155.8(6) . . . . ? N3A Cu1A N1A C8A -151.8(6) . . . . ? N2A Cu1A N1A C8A -34.4(6) . . . . ? I1A Cu1A N1A C8A 63.3(6) . . . . ? C1A Cu1A N1A C7A 25.4(5) . . . . ? N3A Cu1A N1A C7A 77.7(7) . . . . ? N2A Cu1A N1A C7A -164.8(5) . . . . ? I1A Cu1A N1A C7A -67.2(5) . . . . ? C1A Cu1A N2A C10A 114.7(17) . . . . ? N3A Cu1A N2A C10A -168.3(6) . . . . ? N1A Cu1A N2A C10A 36.3(6) . . . . ? I1A Cu1A N2A C10A -65.2(6) . . . . ? C1A Cu1A N2A C11A -114.2(17) . . . . ? N3A Cu1A N2A C11A -37.2(5) . . . . ? N1A Cu1A N2A C11A 167.5(5) . . . . ? I1A Cu1A N2A C11A 66.0(5) . . . . ? C6A C1A C2A C3A -1.7(11) . . . . ? Cu1A C1A C2A C3A 174.1(5) . . . . ? C6A C1A C2A C7A 175.7(7) . . . . ? Cu1A C1A C2A C7A -8.5(9) . . . . ? C1A Cu1A N3A C14A -23.9(5) . . . . ? N2A Cu1A N3A C14A 166.2(5) . . . . ? N1A Cu1A N3A C14A -76.3(7) . . . . ? I1A Cu1A N3A C14A 68.4(5) . . . . ? C1A Cu1A N3A C13A -152.0(6) . . . . ? N2A Cu1A N3A C13A 38.2(5) . . . . ? N1A Cu1A N3A C13A 155.6(6) . . . . ? I1A Cu1A N3A C13A -59.7(5) . . . . ? C1A C2A C3A C4A 0.8(11) . . . . ? C7A C2A C3A C4A -176.1(8) . . . . ? C2A C3A C4A C5A 0.5(13) . . . . ? C3A C4A C5A C6A -1.1(13) . . . . ? C2A C1A C6A C5A 1.2(11) . . . . ? Cu1A C1A C6A C5A -174.7(5) . . . . ? C2A C1A C6A C14A -175.4(7) . . . . ? Cu1A C1A C6A C14A 8.8(8) . . . . ? C4A C5A C6A C1A 0.3(11) . . . . ? C4A C5A C6A C14A 176.3(8) . . . . ? C8A N1A C7A C2A -168.1(7) . . . . ? Cu1A N1A C7A C2A -34.7(7) . . . . ? C1A C2A C7A N1A 28.1(9) . . . . ? C3A C2A C7A N1A -154.9(8) . . . . ? C7A N1A C8A C9A 179.4(8) . . . . ? Cu1A N1A C8A C9A 49.5(10) . . . . ? N1A C8A C9A C10A -64.6(12) . . . . ? C8A C9A C10A N2A 68.6(11) . . . . ? C11A N2A C10A C9A 171.7(7) . . . . ? Cu1A N2A C10A C9A -55.5(9) . . . . ? C10A N2A C11A C12A -171.1(7) . . . . ? Cu1A N2A C11A C12A 56.1(8) . . . . ? N2A C11A C12A C13A -72.3(10) . . . . ? C14A N3A C13A C12A 175.8(7) . . . . ? Cu1A N3A C13A C12A -55.5(8) . . . . ? C11A C12A C13A N3A 71.4(10) . . . . ? C1A C6A C14A N3A -26.8(8) . . . . ? C5A C6A C14A N3A 157.2(7) . . . . ? C13A N3A C14A C6A 164.0(6) . . . . ? Cu1A N3A C14A C6A 32.8(7) . . . . ? C1C Cu1C N1C C8C -150.6(7) . . . . ? N3C Cu1C N1C C8C 161.0(8) . . . . ? N2C Cu1C N1C C8C 38.5(7) . . . . ? I1C Cu1C N1C C8C -57.2(7) . . . . ? C1C Cu1C N1C C7C -16.3(6) . . . . ? N3C Cu1C N1C C7C -64.7(10) . . . . ? N2C Cu1C N1C C7C 172.8(6) . . . . ? I1C Cu1C N1C C7C 77.1(6) . . . . ? N3C Cu1C C1C C6C -9.4(6) . . . . ? N1C Cu1C C1C C6C -170.9(6) . . . . ? N2C Cu1C C1C C6C -96(2) . . . . ? I1C Cu1C C1C C6C 88.1(6) . . . . ? N3C Cu1C C1C C2C 167.4(6) . . . . ? N1C Cu1C C1C C2C 5.9(6) . . . . ? N2C Cu1C C1C C2C 81(2) . . . . ? I1C Cu1C C1C C2C -95.1(6) . . . . ? C1C Cu1C N2C C11C 114(2) . . . . ? N3C Cu1C N2C C11C 29.5(7) . . . . ? N1C Cu1C N2C C11C -171.4(7) . . . . ? I1C Cu1C N2C C11C -69.3(7) . . . . ? C1C Cu1C N2C C10C -110(2) . . . . ? N3C Cu1C N2C C10C 164.7(7) . . . . ? N1C Cu1C N2C C10C -36.2(7) . . . . ? I1C Cu1C N2C C10C 65.8(7) . . . . ? C6C C1C C2C C3C -0.1(12) . . . . ? Cu1C C1C C2C C3C -176.6(6) . . . . ? C6C C1C C2C C7C -177.3(8) . . . . ? Cu1C C1C C2C C7C 6.2(10) . . . . ? C1C Cu1C N3C C14C 22.8(7) . . . . ? N1C Cu1C N3C C14C 71.3(11) . . . . ? N2C Cu1C N3C C14C -166.7(7) . . . . ? I1C Cu1C N3C C14C -71.0(7) . . . . ? C1C Cu1C N3C C13C 157.6(8) . . . . ? N1C Cu1C N3C C13C -153.9(8) . . . . ? N2C Cu1C N3C C13C -31.9(8) . . . . ? I1C Cu1C N3C C13C 63.8(8) . . . . ? C1C C2C C3C C4C -0.1(14) . . . . ? C7C C2C C3C C4C 176.7(10) . . . . ? C2C C3C C4C C5C 0.6(19) . . . . ? C3C C4C C5C C6C -1(2) . . . . ? C2C C1C C6C C5C -0.2(12) . . . . ? Cu1C C1C C6C C5C 176.3(6) . . . . ? C2C C1C C6C C14C 177.8(8) . . . . ? Cu1C C1C C6C C14C -5.7(10) . . . . ? C4C C5C C6C C1C 0.7(15) . . . . ? C4C C5C C6C C14C -176.9(11) . . . . ? C1C C2C C7C N1C -18.6(11) . . . . ? C3C C2C C7C N1C 164.6(8) . . . . ? C8C N1C C7C C2C 158.0(7) . . . . ? Cu1C N1C C7C C2C 22.6(9) . . . . ? C7C N1C C8C C9C 169.6(9) . . . . ? Cu1C N1C C8C C9C -56.4(11) . . . . ? N1C C8C C9C C10C 67.8(12) . . . . ? C8C C9C C10C N2C -66.0(13) . . . . ? C11C N2C C10C C9C -169.3(9) . . . . ? Cu1C N2C C10C C9C 52.4(11) . . . . ? C10C N2C C11C C12C 175.0(11) . . . . ? Cu1C N2C C11C C12C -47.6(13) . . . . ? N2C C11C C12C C13C 65.6(15) . . . . ? C14C N3C C13C C12C -173.2(10) . . . . ? Cu1C N3C C13C C12C 52.2(12) . . . . ? C11C C12C C13C N3C -68.1(14) . . . . ? C13C N3C C14C C6C -166.5(8) . . . . ? Cu1C N3C C14C C6C -29.9(9) . . . . ? C1C C6C C14C N3C 22.7(10) . . . . ? C5C C6C C14C N3C -159.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 4.460 _refine_diff_density_min -2.273 _refine_diff_density_rms 0.169