# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Diez-Gonzalez, Silvia' _publ_contact_author_email s.diez-gonzalez@imperial.ac.uk _publ_section_title ; [(NHC)CuX] Complexes: Synthesis, Characterization and Catalytic Activities in Reduction Reactions and Click Chemistry. On the Advantage of Using Well-Defined Catalytic Systems ; _publ_author_name S.Diez-Gonzalez # Attachment '- 1b-CCDC750314.txt' data_nol199m _database_code_depnum_ccdc_archive 'CCDC 750314' #TrackingRef '- 1b-CCDC750314.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H36 Br Cu N2' _chemical_formula_weight 532.03 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 Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.7030(4) _cell_length_b 12.7140(5) _cell_length_c 19.4880(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2651.89(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 23412 _cell_measurement_theta_min 2.171 _cell_measurement_theta_max 30.499 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 2.346 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.698059 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 42336 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0136 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 30.50 _reflns_number_total 4052 _reflns_number_gt 3288 _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 '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^)+(0.0418P)^2^+3.0473P] 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 4052 _refine_ls_number_parameters 214 _refine_ls_number_restraints 130 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.2500 0.7500 0.719943(14) 0.01972(9) Uani 1 2 d SU . . Br1 Br -0.2500 0.7500 0.833293(15) 0.04229(11) Uani 1 2 d SU . . N1 N -0.21940(14) 0.83001(11) 0.58078(7) 0.0182(3) Uani 1 1 d U . . C1 C -0.17662(16) 0.93129(12) 0.60473(8) 0.0190(3) Uani 1 1 d U . . C2 C -0.04785(17) 0.94599(14) 0.61289(10) 0.0242(3) Uani 1 1 d U . . C3 C -0.0080(2) 1.04289(16) 0.63806(12) 0.0316(4) Uani 1 1 d U . . H3 H 0.073(2) 1.0538(19) 0.6426(13) 0.031(6) Uiso 1 1 d . . . C4 C -0.0931(2) 1.12054(16) 0.65435(13) 0.0362(5) Uani 1 1 d U . . H4 H -0.062(3) 1.181(2) 0.6698(14) 0.045(8) Uiso 1 1 d . . . C5 C -0.2197(2) 1.10421(16) 0.64534(12) 0.0334(4) Uani 1 1 d U . . H5 H -0.272(3) 1.151(2) 0.6579(14) 0.041(8) Uiso 1 1 d . . . C6 C -0.26511(17) 1.00893(14) 0.61940(10) 0.0242(3) Uani 1 1 d U . . C7 C 0.04541(19) 0.85844(17) 0.59890(12) 0.0303(4) Uani 1 1 d U . . H7 H 0.009(2) 0.812(2) 0.5731(13) 0.032(6) Uiso 1 1 d . . . C8 C 0.0877(2) 0.8086(2) 0.66614(14) 0.0434(6) Uani 1 1 d U . . H8A H 0.134(3) 0.747(2) 0.6566(15) 0.047(8) Uiso 1 1 d . . . H8B H 0.024(3) 0.788(3) 0.6931(18) 0.059(9) Uiso 1 1 d . . . H8C H 0.137(3) 0.854(3) 0.6931(17) 0.053(9) Uiso 1 1 d . . . C9 C 0.1576(3) 0.8967(3) 0.55682(17) 0.0495(7) Uani 1 1 d U . . H9A H 0.208(3) 0.837(3) 0.5428(16) 0.055(9) Uiso 1 1 d . . . H9B H 0.129(3) 0.927(2) 0.5130(16) 0.050(8) Uiso 1 1 d . . . H9C H 0.203(4) 0.938(3) 0.5844(19) 0.074(12) Uiso 1 1 d . . . C10 C -0.40436(18) 0.99339(16) 0.60952(11) 0.0289(4) Uani 1 1 d U . . H10 H -0.416(2) 0.934(2) 0.5830(13) 0.032(6) Uiso 1 1 d . . . C11 C -0.4633(2) 1.0832(2) 0.56809(14) 0.0418(5) Uani 1 1 d U . . H11A H -0.465(3) 1.150(2) 0.5956(15) 0.049(8) Uiso 1 1 d . . . H11B H -0.549(3) 1.073(2) 0.5572(16) 0.052(8) Uiso 1 1 d . . . H11C H -0.418(3) 1.089(2) 0.5210(16) 0.051(9) Uiso 1 1 d . . . C12 C -0.4707(3) 0.9804(3) 0.67829(15) 0.0468(6) Uani 1 1 d U . . H12A H -0.439(3) 0.922(3) 0.7061(17) 0.055(9) Uiso 1 1 d . . . H12B H -0.566(3) 0.971(3) 0.6700(17) 0.064(10) Uiso 1 1 d . . . H12C H -0.463(3) 1.045(3) 0.7048(18) 0.065(10) Uiso 1 1 d . . . C13 C -0.2500 0.7500 0.62326(12) 0.0160(4) Uani 1 2 d SU . . C14 C -0.23059(18) 0.80045(14) 0.51257(9) 0.0222(3) Uani 1 1 d U . . H14 H -0.213(2) 0.8408(18) 0.4786(10) 0.015(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02347(15) 0.02216(15) 0.01354(14) 0.000 0.000 0.00147(11) Br1 0.0533(2) 0.0569(2) 0.01666(14) 0.000 0.000 0.02429(16) N1 0.0240(7) 0.0156(6) 0.0150(6) -0.0004(5) 0.0007(5) -0.0005(5) C1 0.0257(8) 0.0142(7) 0.0170(7) 0.0018(6) -0.0012(6) -0.0019(6) C2 0.0248(8) 0.0211(8) 0.0265(8) 0.0051(6) -0.0030(7) 0.0003(6) C3 0.0283(10) 0.0260(9) 0.0406(11) 0.0042(8) -0.0110(8) -0.0056(7) C4 0.0431(12) 0.0195(9) 0.0459(12) -0.0024(8) -0.0146(10) -0.0046(8) C5 0.0382(11) 0.0195(8) 0.0425(12) -0.0072(8) -0.0084(9) 0.0037(8) C6 0.0267(8) 0.0200(7) 0.0257(8) -0.0027(6) -0.0041(7) 0.0009(6) C7 0.0248(9) 0.0281(9) 0.0378(11) 0.0048(8) 0.0001(8) 0.0025(7) C8 0.0302(11) 0.0485(14) 0.0513(14) 0.0244(12) 0.0087(10) 0.0133(10) C9 0.0421(14) 0.0523(16) 0.0541(17) 0.0212(13) 0.0181(12) 0.0096(12) C10 0.0251(8) 0.0265(9) 0.0352(10) -0.0083(8) -0.0015(7) 0.0028(7) C11 0.0378(12) 0.0410(12) 0.0466(13) -0.0073(10) -0.0137(10) 0.0102(10) C12 0.0371(12) 0.0580(16) 0.0453(14) -0.0009(12) 0.0094(11) 0.0017(12) C13 0.0159(9) 0.0139(9) 0.0184(10) 0.000 0.000 -0.0008(7) C14 0.0321(9) 0.0212(8) 0.0131(7) 0.0035(6) 0.0014(6) 0.0008(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 Cu1 C13 1.884(2) . ? Cu1 Br1 2.2090(4) . ? N1 C13 1.352(2) . ? N1 C14 1.387(2) . ? N1 C1 1.444(2) . ? C1 C6 1.398(2) . ? C1 C2 1.400(3) . ? C2 C3 1.393(3) . ? C2 C7 1.520(3) . ? C3 C4 1.380(3) . ? C4 C5 1.382(3) . ? C5 C6 1.400(3) . ? C6 C10 1.516(3) . ? C7 C8 1.525(3) . ? C7 C9 1.533(3) . ? C10 C12 1.525(3) . ? C10 C11 1.534(3) . ? C13 N1 1.352(2) 2_465 ? C14 C14 1.349(4) 2_465 ? 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 C13 Cu1 Br1 180.0 . . ? C13 N1 C14 111.23(15) . . ? C13 N1 C1 123.36(14) . . ? C14 N1 C1 125.37(14) . . ? C6 C1 C2 123.34(16) . . ? C6 C1 N1 118.75(16) . . ? C2 C1 N1 117.90(15) . . ? C3 C2 C1 117.37(17) . . ? C3 C2 C7 120.65(18) . . ? C1 C2 C7 121.90(17) . . ? C4 C3 C2 120.75(19) . . ? C3 C4 C5 120.69(19) . . ? C4 C5 C6 121.08(19) . . ? C1 C6 C5 116.74(17) . . ? C1 C6 C10 123.25(16) . . ? C5 C6 C10 120.00(17) . . ? C2 C7 C8 110.21(19) . . ? C2 C7 C9 112.22(19) . . ? C8 C7 C9 111.1(2) . . ? C6 C10 C12 111.10(19) . . ? C6 C10 C11 111.97(19) . . ? C12 C10 C11 110.6(2) . . ? N1 C13 N1 104.5(2) 2_465 . ? N1 C13 Cu1 127.76(10) 2_465 . ? N1 C13 Cu1 127.76(10) . . ? C14 C14 N1 106.53(9) 2_465 . ? 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 C13 N1 C1 C6 -88.24(19) . . . . ? C14 N1 C1 C6 94.1(2) . . . . ? C13 N1 C1 C2 90.94(19) . . . . ? C14 N1 C1 C2 -86.8(2) . . . . ? C6 C1 C2 C3 1.1(3) . . . . ? N1 C1 C2 C3 -178.04(16) . . . . ? C6 C1 C2 C7 177.72(18) . . . . ? N1 C1 C2 C7 -1.4(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C7 C2 C3 C4 -176.4(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? N1 C1 C6 C5 177.25(17) . . . . ? C2 C1 C6 C10 179.06(18) . . . . ? N1 C1 C6 C10 -1.8(3) . . . . ? C4 C5 C6 C1 1.4(3) . . . . ? C4 C5 C6 C10 -179.5(2) . . . . ? C3 C2 C7 C8 75.5(3) . . . . ? C1 C2 C7 C8 -101.0(2) . . . . ? C3 C2 C7 C9 -48.8(3) . . . . ? C1 C2 C7 C9 134.7(2) . . . . ? C1 C6 C10 C12 106.5(2) . . . . ? C5 C6 C10 C12 -72.6(3) . . . . ? C1 C6 C10 C11 -129.3(2) . . . . ? C5 C6 C10 C11 51.6(3) . . . . ? C14 N1 C13 N1 -0.05(9) . . . 2_465 ? C1 N1 C13 N1 -178.04(19) . . . 2_465 ? C14 N1 C13 Cu1 179.95(9) . . . . ? C1 N1 C13 Cu1 1.96(19) . . . . ? Br1 Cu1 C13 N1 -174(100) . . . 2_465 ? Br1 Cu1 C13 N1 6(100) . . . . ? C13 N1 C14 C14 0.1(2) . . . 2_465 ? C1 N1 C14 C14 178.08(19) . . . 2_465 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.617 _refine_diff_density_min -0.954 _refine_diff_density_rms 0.068 # Attachment '- 1c-CCDC750315.txt' data_nol158c _database_code_depnum_ccdc_archive 'CCDC 750315' #TrackingRef '- 1c-CCDC750315.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Cu(IPr)Cl) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H36 Cu I N2' _chemical_formula_weight 579.02 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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.9153(7) _cell_length_b 12.6813(8) _cell_length_c 20.1285(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2786.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.907 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.888871 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 21160 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 22.49 _reflns_number_total 1821 _reflns_number_gt 1606 _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 '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^)+(0.0463P)^2^+11.0816P] 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 1821 _refine_ls_number_parameters 181 _refine_ls_number_restraints 130 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.2500 0.2500 0.28562(4) 0.0249(3) Uani 1 2 d SU . . I1 I -0.2500 0.2500 0.16736(2) 0.0402(2) Uani 1 2 d SU . . C1 C -0.1777(4) 0.4319(4) 0.3964(2) 0.0177(10) Uani 1 1 d U . . N1 N -0.2191(3) 0.3302(3) 0.42034(18) 0.0163(9) Uani 1 1 d U . . C2 C -0.2652(5) 0.5093(4) 0.3830(3) 0.0261(11) Uani 1 1 d U . . C3 C -0.2192(5) 0.6033(4) 0.3557(3) 0.0360(14) Uani 1 1 d U . . H3 H -0.276(5) 0.659(5) 0.346(3) 0.041(17) Uiso 1 1 d . . . C4 C -0.0956(6) 0.6179(4) 0.3453(3) 0.0396(14) Uani 1 1 d U . . H4 H -0.067(5) 0.678(5) 0.330(3) 0.032(15) Uiso 1 1 d . . . C5 C -0.0139(6) 0.5399(4) 0.3601(3) 0.0334(13) Uani 1 1 d U . . H5 H 0.064(6) 0.547(4) 0.356(3) 0.042(18) Uiso 1 1 d . . . C6 C -0.0521(5) 0.4442(4) 0.3867(3) 0.0240(11) Uani 1 1 d U . . C7 C -0.4005(5) 0.4959(4) 0.3931(3) 0.0298(12) Uani 1 1 d U . . H7 H -0.413(4) 0.440(4) 0.419(2) 0.016(13) Uiso 1 1 d . . . C8 C -0.4547(7) 0.5848(6) 0.4343(4) 0.0456(16) Uani 1 1 d U . . H8A H -0.541(7) 0.576(6) 0.446(4) 0.08(2) Uiso 1 1 d . . . H8B H -0.415(6) 0.590(5) 0.475(3) 0.05(2) Uiso 1 1 d . . . H8C H -0.449(6) 0.656(6) 0.405(3) 0.07(2) Uiso 1 1 d . . . C9 C -0.4685(6) 0.4837(5) 0.3273(3) 0.0520(17) Uani 1 1 d U . . H9A H -0.4597 0.5484 0.3012 0.078 Uiso 1 1 calc R . . H9B H -0.5555 0.4705 0.3360 0.078 Uiso 1 1 calc R . . H9C H -0.4340 0.4242 0.3025 0.078 Uiso 1 1 calc R . . C10 C 0.0404(5) 0.3572(4) 0.4002(3) 0.0319(13) Uani 1 1 d U . . H10 H 0.000(5) 0.302(5) 0.424(3) 0.044(17) Uiso 1 1 d . . . C11 C 0.1454(6) 0.3949(5) 0.4438(4) 0.0567(19) Uani 1 1 d U . . H11A H 0.1955 0.4456 0.4190 0.085 Uiso 1 1 calc R . . H11B H 0.1961 0.3345 0.4568 0.085 Uiso 1 1 calc R . . H11C H 0.1124 0.4289 0.4837 0.085 Uiso 1 1 calc R . . C12 C 0.0867(6) 0.3106(5) 0.3351(3) 0.0488(17) Uani 1 1 d U . . H12A H 0.1393 0.3622 0.3126 0.073 Uiso 1 1 calc R . . H12B H 0.0169 0.2933 0.3065 0.073 Uiso 1 1 calc R . . H12C H 0.1339 0.2465 0.3443 0.073 Uiso 1 1 calc R . . C13 C -0.2500 0.2500 0.3785(4) 0.0335(17) Uani 1 2 d SU . . C14 C -0.2300(5) 0.3011(4) 0.4875(3) 0.0257(12) Uani 1 1 d U . . H14 H -0.211(5) 0.351(5) 0.522(3) 0.038(16) 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 0.0307(5) 0.0271(5) 0.0168(5) 0.000 0.000 0.0004(4) I1 0.0494(4) 0.0535(4) 0.0177(3) 0.000 0.000 0.0271(3) C1 0.025(2) 0.013(2) 0.015(2) -0.0031(19) 0.002(2) 0.0000(19) N1 0.016(2) 0.018(2) 0.015(2) 0.0042(15) -0.0021(16) 0.0017(16) C2 0.026(2) 0.021(2) 0.031(3) 0.005(2) 0.008(2) 0.001(2) C3 0.040(3) 0.021(3) 0.047(3) 0.007(2) 0.009(3) 0.005(2) C4 0.048(3) 0.016(3) 0.055(4) 0.006(3) 0.017(3) -0.007(2) C5 0.030(3) 0.021(3) 0.050(4) -0.005(2) 0.013(3) -0.007(2) C6 0.027(2) 0.017(2) 0.029(3) -0.006(2) 0.004(2) 0.000(2) C7 0.030(3) 0.017(3) 0.042(3) 0.012(3) 0.002(2) 0.003(2) C8 0.047(4) 0.046(4) 0.044(4) 0.007(3) 0.016(3) 0.019(3) C9 0.037(4) 0.059(4) 0.060(4) -0.005(3) -0.015(3) 0.001(3) C10 0.023(3) 0.024(3) 0.048(3) -0.007(3) -0.002(2) 0.001(2) C11 0.049(4) 0.053(4) 0.068(5) -0.025(4) -0.022(3) 0.010(3) C12 0.032(3) 0.051(4) 0.063(4) -0.024(3) -0.006(3) 0.014(3) C13 0.041(4) 0.028(4) 0.032(3) 0.000 0.000 -0.009(4) C14 0.033(3) 0.019(2) 0.025(3) -0.002(2) -0.002(2) -0.002(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 Cu1 C13 1.869(8) . ? Cu1 I1 2.3803(10) . ? C1 C6 1.393(7) . ? C1 C2 1.396(7) . ? C1 N1 1.448(6) . ? N1 C13 1.364(7) . ? N1 C14 1.406(7) . ? C2 C3 1.406(7) . ? C2 C7 1.500(7) . ? C3 C4 1.377(8) . ? C4 C5 1.365(8) . ? C5 C6 1.390(7) . ? C6 C10 1.521(7) . ? C7 C8 1.520(8) . ? C7 C9 1.526(8) . ? C10 C11 1.521(8) . ? C10 C12 1.523(8) . ? C13 N1 1.364(7) 2_455 ? C14 C14 1.368(11) 2_455 ? 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 C13 Cu1 I1 180.000(1) . . ? C6 C1 C2 124.6(5) . . ? C6 C1 N1 117.0(4) . . ? C2 C1 N1 118.4(4) . . ? C13 N1 C14 112.2(4) . . ? C13 N1 C1 122.4(4) . . ? C14 N1 C1 125.4(4) . . ? C1 C2 C3 115.3(5) . . ? C1 C2 C7 124.6(4) . . ? C3 C2 C7 120.1(5) . . ? C4 C3 C2 121.6(5) . . ? C5 C4 C3 120.6(6) . . ? C4 C5 C6 121.4(6) . . ? C5 C6 C1 116.6(5) . . ? C5 C6 C10 120.2(5) . . ? C1 C6 C10 123.1(5) . . ? C2 C7 C8 111.9(5) . . ? C2 C7 C9 111.8(5) . . ? C8 C7 C9 111.1(5) . . ? C6 C10 C11 112.0(5) . . ? C6 C10 C12 110.4(5) . . ? C11 C10 C12 111.6(5) . . ? N1 C13 N1 103.6(6) 2_455 . ? N1 C13 Cu1 128.2(3) 2_455 . ? N1 C13 Cu1 128.2(3) . . ? C14 C14 N1 106.0(3) 2_455 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 N1 C13 -89.7(5) . . . . ? C2 C1 N1 C13 88.5(5) . . . . ? C6 C1 N1 C14 88.8(6) . . . . ? C2 C1 N1 C14 -93.0(6) . . . . ? C6 C1 C2 C3 2.2(8) . . . . ? N1 C1 C2 C3 -175.9(4) . . . . ? C6 C1 C2 C7 179.6(5) . . . . ? N1 C1 C2 C7 1.6(8) . . . . ? C1 C2 C3 C4 -1.9(8) . . . . ? C7 C2 C3 C4 -179.5(6) . . . . ? C2 C3 C4 C5 1.3(10) . . . . ? C3 C4 C5 C6 -0.8(10) . . . . ? C4 C5 C6 C1 0.9(8) . . . . ? C4 C5 C6 C10 177.7(6) . . . . ? C2 C1 C6 C5 -1.7(8) . . . . ? N1 C1 C6 C5 176.4(4) . . . . ? C2 C1 C6 C10 -178.4(5) . . . . ? N1 C1 C6 C10 -0.3(7) . . . . ? C1 C2 C7 C8 128.0(6) . . . . ? C3 C2 C7 C8 -54.6(7) . . . . ? C1 C2 C7 C9 -106.6(6) . . . . ? C3 C2 C7 C9 70.7(7) . . . . ? C5 C6 C10 C11 54.3(8) . . . . ? C1 C6 C10 C11 -129.2(6) . . . . ? C5 C6 C10 C12 -70.7(7) . . . . ? C1 C6 C10 C12 105.8(6) . . . . ? C14 N1 C13 N1 0.2(3) . . . 2_455 ? C1 N1 C13 N1 178.9(4) . . . 2_455 ? C14 N1 C13 Cu1 -179.8(3) . . . . ? C1 N1 C13 Cu1 -1.1(4) . . . . ? I1 Cu1 C13 N1 -55(100) . . . 2_455 ? I1 Cu1 C13 N1 125(100) . . . . ? C13 N1 C14 C14 -0.4(7) . . . 2_455 ? C1 N1 C14 C14 -179.1(5) . . . 2_455 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.290 _refine_diff_density_min -1.131 _refine_diff_density_rms 0.082 # Attachment '- 2c-CCDC750316.txt' data_sd016b_0m _database_code_depnum_ccdc_archive 'CCDC 750316' #TrackingRef '- 2c-CCDC750316.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H38 Cu I N2' _chemical_formula_weight 581.03 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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 10.9969(3) _cell_length_b 12.5666(3) _cell_length_c 19.9092(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2751.32(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8418 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 39.18 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.931 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7330 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 25238 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 39.79 _reflns_number_total 7571 _reflns_number_gt 5706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.1-0' _computing_cell_refinement 'Bruker APEX2 v2009.1-0' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0382P)^2^+1.0341P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7571 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 I1 I 0.7500 0.2500 0.330037(5) 0.02892(4) Uani 1 2 d S . . Cu1 Cu 0.7500 0.2500 0.210475(10) 0.01525(4) Uani 1 2 d S . . C1 C 0.7500 0.2500 0.11570(7) 0.0133(2) Uani 1 2 d S . . N1 N 0.71891(10) 0.16827(8) 0.07664(5) 0.01527(16) Uani 1 1 d . . . C2 C 0.72268(12) 0.19391(9) 0.00449(5) 0.01683(19) Uani 1 1 d . . . H2A H 0.6402 0.1935 -0.0154 0.020 Uiso 1 1 calc R . . H2B H 0.7749 0.1433 -0.0204 0.020 Uiso 1 1 calc R . . C3 C 0.67605(11) 0.06911(9) 0.10259(6) 0.01572(18) Uani 1 1 d . . . C4 C 0.55125(11) 0.05654(10) 0.11410(6) 0.0194(2) Uani 1 1 d . . . C5 C 0.51194(13) -0.03954(11) 0.14135(8) 0.0265(3) Uani 1 1 d . . . H5A H 0.4277 -0.0505 0.1492 0.032 Uiso 1 1 calc R . . C6 C 0.59348(14) -0.11897(11) 0.15707(9) 0.0302(3) Uani 1 1 d . . . H6A H 0.5652 -0.1837 0.1761 0.036 Uiso 1 1 calc R . . C7 C 0.71644(14) -0.10476(11) 0.14527(9) 0.0283(3) Uani 1 1 d . . . H7A H 0.7718 -0.1599 0.1567 0.034 Uiso 1 1 calc R . . C8 C 0.76052(11) -0.01110(10) 0.11696(7) 0.0198(2) Uani 1 1 d . . . C9 C 0.46097(12) 0.14501(11) 0.10066(8) 0.0241(2) Uani 1 1 d . . . H9A H 0.5050 0.2034 0.0767 0.029 Uiso 1 1 calc R . . C10 C 0.41305(15) 0.19006(14) 0.16686(9) 0.0347(4) Uani 1 1 d . . . H10A H 0.4816 0.2131 0.1948 0.052 Uiso 1 1 calc R . . H10B H 0.3669 0.1350 0.1906 0.052 Uiso 1 1 calc R . . H10C H 0.3600 0.2510 0.1576 0.052 Uiso 1 1 calc R . . C11 C 0.35719(18) 0.10804(15) 0.05553(11) 0.0426(4) Uani 1 1 d . . . H11A H 0.3905 0.0796 0.0136 0.064 Uiso 1 1 calc R . . H11B H 0.3037 0.1684 0.0455 0.064 Uiso 1 1 calc R . . H11C H 0.3106 0.0524 0.0785 0.064 Uiso 1 1 calc R . . C12 C 0.89518(12) 0.00198(11) 0.10426(8) 0.0256(3) Uani 1 1 d . . . H12A H 0.9068 0.0690 0.0779 0.031 Uiso 1 1 calc R . . C13 C 0.96451(17) 0.01416(17) 0.17058(10) 0.0399(4) Uani 1 1 d . . . H13A H 0.9300 0.0734 0.1963 0.060 Uiso 1 1 calc R . . H13B H 1.0504 0.0286 0.1612 0.060 Uiso 1 1 calc R . . H13C H 0.9575 -0.0517 0.1967 0.060 Uiso 1 1 calc R . . C14 C 0.94631(16) -0.08964(14) 0.06262(9) 0.0349(3) Uani 1 1 d . . . H14A H 0.9005 -0.0957 0.0206 0.052 Uiso 1 1 calc R . . H14B H 0.9392 -0.1561 0.0880 0.052 Uiso 1 1 calc R . . H14C H 1.0321 -0.0759 0.0525 0.052 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 0.03416(8) 0.04112(9) 0.01149(5) 0.000 0.000 0.01863(5) Cu1 0.01806(9) 0.01671(10) 0.01097(7) 0.000 0.000 0.00018(6) C1 0.0152(6) 0.0119(6) 0.0128(5) 0.000 0.000 -0.0001(4) N1 0.0206(4) 0.0123(4) 0.0129(3) 0.0006(3) -0.0007(3) -0.0023(3) C2 0.0239(5) 0.0151(5) 0.0115(4) -0.0007(3) 0.0002(3) -0.0003(4) C3 0.0186(5) 0.0112(4) 0.0173(4) 0.0000(3) 0.0017(3) -0.0017(3) C4 0.0194(5) 0.0150(5) 0.0239(5) -0.0031(4) 0.0041(4) -0.0005(4) C5 0.0230(6) 0.0180(6) 0.0386(7) -0.0014(5) 0.0099(5) -0.0048(4) C6 0.0325(7) 0.0157(6) 0.0424(8) 0.0046(5) 0.0134(6) -0.0038(5) C7 0.0300(7) 0.0153(6) 0.0395(7) 0.0089(5) 0.0082(6) 0.0025(5) C8 0.0199(5) 0.0146(5) 0.0251(5) 0.0045(4) 0.0028(4) -0.0002(4) C9 0.0190(6) 0.0200(6) 0.0333(6) -0.0048(5) 0.0017(5) 0.0016(4) C10 0.0241(7) 0.0365(8) 0.0435(9) -0.0157(7) 0.0013(6) 0.0085(5) C11 0.0383(9) 0.0390(9) 0.0504(11) -0.0167(8) -0.0176(8) 0.0107(7) C12 0.0199(6) 0.0218(6) 0.0349(7) 0.0097(5) 0.0015(5) 0.0022(4) C13 0.0288(8) 0.0476(10) 0.0434(10) 0.0013(7) -0.0076(7) 0.0023(7) C14 0.0300(8) 0.0368(8) 0.0379(8) 0.0079(6) 0.0125(6) 0.0078(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu1 2.3804(2) . ? Cu1 C1 1.8868(15) . ? C1 N1 1.3329(13) . ? C1 N1 1.3330(13) 2_655 ? N1 C3 1.4289(15) . ? N1 C2 1.4727(14) . ? C2 C2 1.532(2) 2_655 ? C3 C8 1.4004(17) . ? C3 C4 1.4004(17) . ? C4 C5 1.3925(18) . ? C4 C9 1.5143(18) . ? C5 C6 1.378(2) . ? C6 C7 1.384(2) . ? C7 C8 1.3920(18) . ? C8 C12 1.5113(18) . ? C9 C11 1.525(2) . ? C9 C10 1.528(2) . ? C12 C14 1.526(2) . ? C12 C13 1.532(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 I1 180.0 . . ? N1 C1 N1 108.61(13) . 2_655 ? N1 C1 Cu1 125.70(7) . . ? N1 C1 Cu1 125.70(7) 2_655 . ? C1 N1 C3 123.07(9) . . ? C1 N1 C2 113.16(10) . . ? C3 N1 C2 123.55(9) . . ? N1 C2 C2 102.26(6) . 2_655 ? C8 C3 C4 122.37(11) . . ? C8 C3 N1 118.87(10) . . ? C4 C3 N1 118.74(11) . . ? C5 C4 C3 117.76(12) . . ? C5 C4 C9 120.13(12) . . ? C3 C4 C9 122.06(11) . . ? C6 C5 C4 120.98(12) . . ? C5 C6 C7 120.25(12) . . ? C6 C7 C8 121.20(13) . . ? C7 C8 C3 117.41(11) . . ? C7 C8 C12 120.06(12) . . ? C3 C8 C12 122.51(11) . . ? C4 C9 C11 111.78(12) . . ? C4 C9 C10 110.22(13) . . ? C11 C9 C10 111.28(13) . . ? C8 C12 C14 111.70(13) . . ? C8 C12 C13 110.74(13) . . ? C14 C12 C13 111.11(13) . . ? 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 I1 Cu1 C1 N1 -80(100) . . . . ? I1 Cu1 C1 N1 100(100) . . . 2_655 ? N1 C1 N1 C3 -177.43(13) 2_655 . . . ? Cu1 C1 N1 C3 2.57(13) . . . . ? N1 C1 N1 C2 -2.64(6) 2_655 . . . ? Cu1 C1 N1 C2 177.36(6) . . . . ? C1 N1 C2 C2 6.36(15) . . . 2_655 ? C3 N1 C2 C2 -178.88(12) . . . 2_655 ? C1 N1 C3 C8 -90.14(14) . . . . ? C2 N1 C3 C8 95.61(15) . . . . ? C1 N1 C3 C4 88.48(14) . . . . ? C2 N1 C3 C4 -85.77(15) . . . . ? C8 C3 C4 C5 0.52(19) . . . . ? N1 C3 C4 C5 -178.05(12) . . . . ? C8 C3 C4 C9 177.86(12) . . . . ? N1 C3 C4 C9 -0.71(18) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C9 C4 C5 C6 -176.71(14) . . . . ? C4 C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C3 1.7(2) . . . . ? C6 C7 C8 C12 -179.64(15) . . . . ? C4 C3 C8 C7 -1.7(2) . . . . ? N1 C3 C8 C7 176.90(12) . . . . ? C4 C3 C8 C12 179.67(13) . . . . ? N1 C3 C8 C12 -1.77(19) . . . . ? C5 C4 C9 C11 -55.64(19) . . . . ? C3 C4 C9 C11 127.08(15) . . . . ? C5 C4 C9 C10 68.66(17) . . . . ? C3 C4 C9 C10 -108.62(15) . . . . ? C7 C8 C12 C14 53.80(19) . . . . ? C3 C8 C12 C14 -127.57(14) . . . . ? C7 C8 C12 C13 -70.62(19) . . . . ? C3 C8 C12 C13 108.01(15) . . . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 39.79 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 1.255 _refine_diff_density_min -0.991 _refine_diff_density_rms 0.084 # Attachment '- 3a-CCDC750317.txt' data_sd014pca21 _database_code_depnum_ccdc_archive 'CCDC 750317' #TrackingRef '- 3a-CCDC750317.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 Cl Cu N2' _chemical_formula_weight 435.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) 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 14.7293(6) _cell_length_b 21.9562(8) _cell_length_c 12.4897(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4039.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8503 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 36.36 _exptl_crystal_description Needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 1.224 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6402 _exptl_absorpt_correction_T_max 0.8874 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_support 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36101 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 37.07 _reflns_number_total 13057 _reflns_number_gt 10396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _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^)+(0.0443P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(7) _refine_ls_number_reflns 13057 _refine_ls_number_parameters 487 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.003 _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 Cu1A Cu 0.553676(14) 0.866942(11) 0.84885(2) 0.01557(5) Uani 1 1 d . . . C1B C 0.49646(10) 0.87276(8) 0.71345(18) 0.0145(3) Uani 1 1 d . . . N1B N 0.43103(9) 0.91342(7) 0.68371(14) 0.0135(3) Uani 1 1 d . . . C2B C 0.40548(11) 0.90406(9) 0.57832(16) 0.0149(3) Uani 1 1 d . . . H2B H 0.3616 0.9267 0.5393 0.018 Uiso 1 1 calc R . . N2B N 0.51030(9) 0.83795(8) 0.62473(14) 0.0135(3) Uani 1 1 d . . . Cl1A Cl 0.61217(3) 0.86227(2) 1.00297(5) 0.02206(10) Uani 1 1 d . . . C3B C 0.45489(11) 0.85644(9) 0.54141(16) 0.0154(3) Uani 1 1 d . . . H3B H 0.4520 0.8391 0.4718 0.019 Uiso 1 1 calc R . . C4B C 0.39115(11) 0.96014(9) 0.75593(16) 0.0138(3) Uani 1 1 d . . . C5B C 0.46187(13) 1.00954(10) 0.78076(19) 0.0204(4) Uani 1 1 d . . . H5B1 H 0.4816 1.0294 0.7136 0.024 Uiso 1 1 calc R . . H5B2 H 0.5157 0.9910 0.8151 0.024 Uiso 1 1 calc R . . C6B C 0.41925(15) 1.05703(10) 0.8563(2) 0.0247(4) Uani 1 1 d . . . H6B H 0.4652 1.0892 0.8726 0.030 Uiso 1 1 calc R . . C7B C 0.38958(15) 1.02642(10) 0.9613(2) 0.0239(4) Uani 1 1 d . . . H7B1 H 0.4427 1.0076 0.9969 0.029 Uiso 1 1 calc R . . H7B2 H 0.3634 1.0572 1.0104 0.029 Uiso 1 1 calc R . . C8B C 0.31872(13) 0.97763(10) 0.93610(18) 0.0181(4) Uani 1 1 d . . . H8B H 0.2990 0.9575 1.0040 0.022 Uiso 1 1 calc R . . C9B C 0.35991(11) 0.93007(8) 0.86087(17) 0.0143(3) Uani 1 1 d . . . H9B1 H 0.3142 0.8983 0.8449 0.017 Uiso 1 1 calc R . . H9B2 H 0.4123 0.9103 0.8962 0.017 Uiso 1 1 calc R . . C10B C 0.23583(14) 1.00644(11) 0.8806(2) 0.0237(4) Uani 1 1 d . . . H10B H 0.1903 0.9746 0.8643 0.028 Uiso 1 1 calc R . . H10C H 0.2074 1.0368 0.9287 0.028 Uiso 1 1 calc R . . C11B C 0.33687(17) 1.08648(11) 0.8023(2) 0.0279(5) Uani 1 1 d . . . H11C H 0.3559 1.1069 0.7353 0.033 Uiso 1 1 calc R . . H11D H 0.3101 1.1175 0.8504 0.033 Uiso 1 1 calc R . . C12B C 0.26628(14) 1.03725(10) 0.77730(19) 0.0227(4) Uani 1 1 d . . . H12C H 0.2126 1.0564 0.7416 0.027 Uiso 1 1 calc R . . C13B C 0.30924(12) 0.99024(9) 0.70130(17) 0.0172(4) Uani 1 1 d . . . H13C H 0.2638 0.9588 0.6823 0.021 Uiso 1 1 calc R . . H13D H 0.3290 1.0106 0.6346 0.021 Uiso 1 1 calc R . . C14B C 0.57465(11) 0.78592(9) 0.61942(16) 0.0133(3) Uani 1 1 d . . . C15B C 0.67079(11) 0.80771(10) 0.64862(19) 0.0181(4) Uani 1 1 d . . . H15C H 0.6907 0.8395 0.5976 0.022 Uiso 1 1 calc R . . H15D H 0.6707 0.8255 0.7214 0.022 Uiso 1 1 calc R . . C16B C 0.73659(12) 0.75345(11) 0.6445(2) 0.0234(5) Uani 1 1 d . . . H16B H 0.7989 0.7676 0.6643 0.028 Uiso 1 1 calc R . . C17B C 0.73834(12) 0.72777(11) 0.5314(2) 0.0252(5) Uani 1 1 d . . . H17C H 0.7816 0.6933 0.5276 0.030 Uiso 1 1 calc R . . H17D H 0.7586 0.7596 0.4806 0.030 Uiso 1 1 calc R . . C18B C 0.64261(12) 0.70579(9) 0.50085(19) 0.0193(4) Uani 1 1 d . . . H18B H 0.6437 0.6888 0.4265 0.023 Uiso 1 1 calc R . . C19B C 0.57622(12) 0.75961(9) 0.50573(18) 0.0172(3) Uani 1 1 d . . . H19C H 0.5953 0.7915 0.4544 0.021 Uiso 1 1 calc R . . H19D H 0.5146 0.7458 0.4855 0.021 Uiso 1 1 calc R . . C20B C 0.54365(11) 0.73608(9) 0.69752(18) 0.0181(4) Uani 1 1 d . . . H20C H 0.5416 0.7526 0.7712 0.022 Uiso 1 1 calc R . . H20D H 0.4819 0.7221 0.6781 0.022 Uiso 1 1 calc R . . C21B C 0.61025(13) 0.68242(10) 0.69256(19) 0.0215(4) Uani 1 1 d . . . H21B H 0.5905 0.6500 0.7436 0.026 Uiso 1 1 calc R . . C22B C 0.70551(13) 0.70531(10) 0.7240(2) 0.0266(5) Uani 1 1 d . . . H22C H 0.7038 0.7229 0.7970 0.032 Uiso 1 1 calc R . . H22D H 0.7489 0.6708 0.7242 0.032 Uiso 1 1 calc R . . C23B C 0.61275(13) 0.65655(10) 0.5786(2) 0.0218(4) Uani 1 1 d . . . H23A H 0.6556 0.6219 0.5755 0.026 Uiso 1 1 calc R . . H23B H 0.5517 0.6415 0.5585 0.026 Uiso 1 1 calc R . . Cl1B Cl 0.39202(3) 0.62640(3) 0.44964(5) 0.02426(11) Uani 1 1 d . . . C1A C 0.12175(10) 0.63175(8) 0.47239(18) 0.0132(3) Uani 1 1 d . . . N1A N 0.07005(9) 0.67067(7) 0.52969(14) 0.0132(3) Uani 1 1 d . . . Cu1B Cu 0.249971(13) 0.629155(10) 0.46395(2) 0.01485(5) Uani 1 1 d . . . C2A C -0.02129(11) 0.66056(9) 0.51007(18) 0.0168(4) Uani 1 1 d . . . H2A H -0.0709 0.6824 0.5398 0.020 Uiso 1 1 calc R . . N2A N 0.06232(9) 0.59639(7) 0.41750(14) 0.0135(3) Uani 1 1 d . . . C3A C -0.02598(11) 0.61387(10) 0.44095(18) 0.0175(4) Uani 1 1 d . . . H3A H -0.0798 0.5961 0.4132 0.021 Uiso 1 1 calc R . . C4A C 0.10796(11) 0.72022(9) 0.59851(16) 0.0131(3) Uani 1 1 d . . . C5A C 0.15315(11) 0.76748(9) 0.52552(16) 0.0150(3) Uani 1 1 d . . . H5A1 H 0.2010 0.7477 0.4820 0.018 Uiso 1 1 calc R . . H5A2 H 0.1075 0.7850 0.4762 0.018 Uiso 1 1 calc R . . C6A C 0.19495(12) 0.81804(10) 0.59411(18) 0.0178(4) Uani 1 1 d . . . H6A H 0.2250 0.8487 0.5467 0.021 Uiso 1 1 calc R . . C7A C 0.26575(12) 0.78979(9) 0.66967(19) 0.0189(4) Uani 1 1 d . . . H7A1 H 0.3134 0.7691 0.6272 0.023 Uiso 1 1 calc R . . H7A2 H 0.2950 0.8222 0.7126 0.023 Uiso 1 1 calc R . . C8A C 0.21960(12) 0.74389(9) 0.74415(17) 0.0172(3) Uani 1 1 d . . . H8A H 0.2657 0.7261 0.7939 0.021 Uiso 1 1 calc R . . C9A C 0.14496(13) 0.77584(10) 0.80966(18) 0.0208(4) Uani 1 1 d . . . H9A1 H 0.1158 0.7463 0.8588 0.025 Uiso 1 1 calc R . . H9A2 H 0.1718 0.8090 0.8531 0.025 Uiso 1 1 calc R . . C10A C 0.07417(12) 0.80204(9) 0.73229(19) 0.0196(4) Uani 1 1 d . . . H10A H 0.0249 0.8224 0.7743 0.023 Uiso 1 1 calc R . . C11A C 0.03258(11) 0.75089(9) 0.66344(19) 0.0171(4) Uani 1 1 d . . . H11A H 0.0026 0.7205 0.7101 0.021 Uiso 1 1 calc R . . H11B H -0.0136 0.7681 0.6145 0.021 Uiso 1 1 calc R . . C12A C 0.11955(13) 0.84900(10) 0.6591(2) 0.0208(4) Uani 1 1 d . . . H12A H 0.1456 0.8823 0.7028 0.025 Uiso 1 1 calc R . . H12B H 0.0739 0.8668 0.6100 0.025 Uiso 1 1 calc R . . C13A C 0.17715(11) 0.69298(9) 0.67691(17) 0.0147(3) Uani 1 1 d . . . H13A H 0.1466 0.6633 0.7244 0.018 Uiso 1 1 calc R . . H13B H 0.2252 0.6713 0.6366 0.018 Uiso 1 1 calc R . . C14A C 0.09095(10) 0.54682(8) 0.34445(18) 0.0138(3) Uani 1 1 d . . . C15A C 0.15052(13) 0.57352(9) 0.25500(17) 0.0180(4) Uani 1 1 d . . . H15A H 0.1151 0.6036 0.2133 0.022 Uiso 1 1 calc R . . H15B H 0.2033 0.5947 0.2869 0.022 Uiso 1 1 calc R . . C16A C 0.18364(14) 0.52289(10) 0.1808(2) 0.0238(4) Uani 1 1 d . . . H16A H 0.2233 0.5406 0.1238 0.029 Uiso 1 1 calc R . . C17A C 0.10242(16) 0.49171(12) 0.1295(2) 0.0274(5) Uani 1 1 d . . . H17A H 0.1235 0.4589 0.0812 0.033 Uiso 1 1 calc R . . H17B H 0.0677 0.5215 0.0863 0.033 Uiso 1 1 calc R . . C18A C 0.04137(12) 0.46497(9) 0.2165(2) 0.0214(4) Uani 1 1 d . . . H18A H -0.0123 0.4450 0.1824 0.026 Uiso 1 1 calc R . . C19A C 0.00841(12) 0.51563(9) 0.2931(2) 0.0191(4) Uani 1 1 d . . . H19A H -0.0278 0.5459 0.2529 0.023 Uiso 1 1 calc R . . H19B H -0.0306 0.4978 0.3496 0.023 Uiso 1 1 calc R . . C20A C 0.14445(12) 0.49886(9) 0.40909(17) 0.0162(3) Uani 1 1 d . . . H20A H 0.1972 0.5183 0.4443 0.019 Uiso 1 1 calc R . . H20B H 0.1051 0.4812 0.4653 0.019 Uiso 1 1 calc R . . C21A C 0.17713(11) 0.44843(9) 0.33339(19) 0.0194(4) Uani 1 1 d . . . H21A H 0.2125 0.4175 0.3749 0.023 Uiso 1 1 calc R . . C22A C 0.09455(13) 0.41759(10) 0.2812(2) 0.0220(4) Uani 1 1 d . . . H22A H 0.1150 0.3843 0.2335 0.026 Uiso 1 1 calc R . . H22B H 0.0550 0.3998 0.3372 0.026 Uiso 1 1 calc R . . C23A C 0.23816(13) 0.47651(10) 0.2468(2) 0.0250(5) Uani 1 1 d . . . H23C H 0.2616 0.4440 0.1993 0.030 Uiso 1 1 calc R . . H23D H 0.2906 0.4970 0.2808 0.030 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 Cu1A 0.01506(8) 0.02120(11) 0.01047(10) -0.00021(10) -0.00248(8) 0.00089(7) C1B 0.0137(6) 0.0181(8) 0.0116(7) 0.0017(7) -0.0013(6) 0.0008(5) N1B 0.0138(5) 0.0156(7) 0.0111(7) -0.0005(6) -0.0009(5) -0.0001(5) C2B 0.0162(6) 0.0183(9) 0.0101(8) -0.0006(7) -0.0006(6) 0.0005(6) N2B 0.0125(5) 0.0179(8) 0.0099(7) -0.0007(6) 0.0002(5) -0.0001(5) Cl1A 0.02194(18) 0.0305(3) 0.0137(2) 0.0041(2) -0.00541(15) -0.00457(17) C3B 0.0153(7) 0.0214(10) 0.0096(8) 0.0010(7) -0.0009(5) -0.0004(6) C4B 0.0159(6) 0.0156(8) 0.0100(8) 0.0000(7) -0.0007(5) -0.0008(6) C5B 0.0227(8) 0.0231(10) 0.0153(10) -0.0007(8) -0.0013(7) -0.0084(7) C6B 0.0399(10) 0.0181(9) 0.0161(10) -0.0025(9) -0.0015(9) -0.0098(8) C7B 0.0389(10) 0.0207(10) 0.0121(9) -0.0019(8) -0.0020(8) -0.0005(8) C8B 0.0248(8) 0.0179(9) 0.0116(9) -0.0005(7) 0.0037(6) 0.0034(7) C9B 0.0170(6) 0.0150(8) 0.0108(8) -0.0018(7) 0.0008(6) 0.0004(5) C10B 0.0280(9) 0.0249(11) 0.0182(10) 0.0000(8) 0.0045(7) 0.0107(8) C11B 0.0507(13) 0.0167(10) 0.0164(11) -0.0012(8) 0.0010(10) 0.0038(9) C12B 0.0316(9) 0.0214(10) 0.0151(10) -0.0014(8) -0.0011(7) 0.0114(8) C13B 0.0213(7) 0.0174(9) 0.0128(9) -0.0008(7) -0.0028(6) 0.0037(6) C14B 0.0120(6) 0.0168(9) 0.0112(8) -0.0004(7) -0.0003(5) -0.0003(6) C15B 0.0130(6) 0.0210(10) 0.0202(10) -0.0046(8) 0.0001(6) -0.0014(6) C16B 0.0120(7) 0.0271(11) 0.0310(13) -0.0092(10) -0.0048(7) 0.0026(7) C17B 0.0160(7) 0.0271(11) 0.0325(13) -0.0096(10) 0.0032(7) 0.0022(7) C18B 0.0199(7) 0.0203(9) 0.0177(9) -0.0041(8) -0.0010(7) 0.0022(6) C19B 0.0184(7) 0.0202(9) 0.0129(9) -0.0026(8) -0.0008(6) 0.0034(6) C20B 0.0193(7) 0.0191(9) 0.0159(10) 0.0016(7) 0.0026(6) -0.0012(6) C21B 0.0277(8) 0.0182(9) 0.0187(11) 0.0023(8) -0.0027(7) 0.0017(7) C22B 0.0279(8) 0.0279(11) 0.0239(12) -0.0052(10) -0.0117(8) 0.0108(8) C23B 0.0225(8) 0.0175(10) 0.0253(11) -0.0027(9) -0.0054(8) 0.0015(7) Cl1B 0.01144(15) 0.0351(3) 0.0262(3) 0.0073(2) 0.00037(15) 0.00161(15) C1A 0.0120(5) 0.0139(8) 0.0139(8) -0.0011(7) 0.0002(6) 0.0011(5) N1A 0.0103(5) 0.0163(7) 0.0129(7) 0.0006(6) 0.0006(5) -0.0007(5) Cu1B 0.00998(7) 0.01909(10) 0.01550(11) -0.00285(11) -0.00013(7) 0.00042(7) C2A 0.0103(6) 0.0189(9) 0.0212(10) 0.0007(8) 0.0001(6) -0.0005(6) N2A 0.0121(5) 0.0152(7) 0.0131(7) 0.0004(6) -0.0014(5) -0.0012(5) C3A 0.0111(6) 0.0222(9) 0.0192(10) 0.0015(8) -0.0009(6) -0.0013(6) C4A 0.0113(6) 0.0151(8) 0.0129(9) -0.0005(6) 0.0008(5) 0.0010(6) C5A 0.0175(7) 0.0162(8) 0.0115(8) 0.0021(7) 0.0004(6) -0.0015(6) C6A 0.0204(7) 0.0166(9) 0.0163(10) 0.0004(7) 0.0002(6) -0.0024(7) C7A 0.0183(7) 0.0207(10) 0.0177(10) -0.0033(8) -0.0007(7) -0.0027(6) C8A 0.0189(7) 0.0211(9) 0.0117(8) -0.0028(7) -0.0009(6) 0.0027(6) C9A 0.0260(8) 0.0236(10) 0.0126(9) -0.0053(8) 0.0035(7) 0.0004(7) C10A 0.0204(7) 0.0199(9) 0.0184(11) -0.0055(8) 0.0034(7) 0.0032(6) C11A 0.0142(6) 0.0162(9) 0.0210(10) -0.0019(8) 0.0023(6) 0.0019(6) C12A 0.0238(8) 0.0153(9) 0.0235(11) -0.0029(8) -0.0014(7) 0.0017(7) C13A 0.0170(7) 0.0153(9) 0.0117(8) -0.0009(7) -0.0001(6) 0.0026(6) C14A 0.0148(6) 0.0141(7) 0.0124(8) -0.0014(7) -0.0017(6) -0.0012(5) C15A 0.0258(8) 0.0172(9) 0.0109(9) -0.0004(7) 0.0025(6) -0.0059(7) C16A 0.0327(9) 0.0229(11) 0.0156(10) -0.0043(8) 0.0074(8) -0.0092(8) C17A 0.0399(11) 0.0255(12) 0.0167(11) -0.0067(9) -0.0021(9) -0.0080(9) C18A 0.0237(7) 0.0178(9) 0.0225(11) -0.0046(9) -0.0048(8) -0.0049(6) C19A 0.0163(7) 0.0177(9) 0.0234(11) -0.0024(8) -0.0039(6) -0.0017(6) C20A 0.0159(7) 0.0167(9) 0.0159(9) 0.0010(7) -0.0007(6) 0.0004(6) C21A 0.0176(7) 0.0179(9) 0.0226(12) -0.0016(8) 0.0009(6) 0.0004(6) C22A 0.0215(8) 0.0166(9) 0.0279(12) -0.0035(8) 0.0012(7) -0.0026(7) C23A 0.0223(8) 0.0235(10) 0.0293(13) -0.0063(9) 0.0093(8) -0.0028(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 Cu1A C1B 1.894(2) . ? Cu1A Cl1A 2.1114(6) . ? C1B N2B 1.361(3) . ? C1B N1B 1.365(2) . ? N1B C2B 1.384(3) . ? N1B C4B 1.487(3) . ? C2B C3B 1.355(3) . ? N2B C3B 1.383(2) . ? N2B C14B 1.486(2) . ? C4B C5B 1.535(3) . ? C4B C13B 1.536(2) . ? C4B C9B 1.538(3) . ? C5B C6B 1.540(3) . ? C6B C11B 1.531(3) . ? C6B C7B 1.537(3) . ? C7B C8B 1.528(3) . ? C8B C9B 1.530(3) . ? C8B C10B 1.540(3) . ? C10B C12B 1.524(3) . ? C11B C12B 1.532(3) . ? C12B C13B 1.538(3) . ? C14B C19B 1.533(3) . ? C14B C20B 1.535(3) . ? C14B C15B 1.539(2) . ? C15B C16B 1.537(3) . ? C16B C17B 1.520(4) . ? C16B C22B 1.521(4) . ? C17B C18B 1.538(3) . ? C18B C23B 1.519(3) . ? C18B C19B 1.535(3) . ? C20B C21B 1.534(3) . ? C21B C23B 1.533(3) . ? C21B C22B 1.541(3) . ? Cl1B Cu1B 2.1008(5) . ? C1A N1A 1.350(2) . ? C1A N2A 1.356(2) . ? C1A Cu1B 1.8923(15) . ? N1A C2A 1.385(2) . ? N1A C4A 1.495(3) . ? C2A C3A 1.342(3) . ? N2A C3A 1.387(2) . ? N2A C14A 1.481(3) . ? C4A C11A 1.531(3) . ? C4A C5A 1.533(3) . ? C4A C13A 1.535(3) . ? C5A C6A 1.532(3) . ? C6A C12A 1.534(3) . ? C6A C7A 1.537(3) . ? C7A C8A 1.531(3) . ? C8A C13A 1.531(3) . ? C8A C9A 1.540(3) . ? C9A C10A 1.534(3) . ? C10A C12A 1.531(3) . ? C10A C11A 1.542(3) . ? C14A C19A 1.536(3) . ? C14A C15A 1.537(3) . ? C14A C20A 1.543(3) . ? C15A C16A 1.527(3) . ? C16A C17A 1.520(3) . ? C16A C23A 1.537(4) . ? C17A C18A 1.528(4) . ? C18A C22A 1.532(3) . ? C18A C19A 1.545(3) . ? C20A C21A 1.533(3) . ? C21A C23A 1.535(3) . ? C21A C22A 1.537(3) . ? 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 C1B Cu1A Cl1A 177.39(6) . . ? N2B C1B N1B 104.56(17) . . ? N2B C1B Cu1A 128.49(13) . . ? N1B C1B Cu1A 126.95(15) . . ? C1B N1B C2B 110.70(17) . . ? C1B N1B C4B 124.40(17) . . ? C2B N1B C4B 124.88(15) . . ? C3B C2B N1B 106.98(17) . . ? C1B N2B C3B 111.06(15) . . ? C1B N2B C14B 124.30(16) . . ? C3B N2B C14B 124.63(17) . . ? C2B C3B N2B 106.70(18) . . ? N1B C4B C5B 109.99(14) . . ? N1B C4B C13B 109.74(16) . . ? C5B C4B C13B 108.59(16) . . ? N1B C4B C9B 109.82(15) . . ? C5B C4B C9B 109.52(16) . . ? C13B C4B C9B 109.17(14) . . ? C4B C5B C6B 108.99(16) . . ? C11B C6B C7B 109.55(19) . . ? C11B C6B C5B 109.9(2) . . ? C7B C6B C5B 110.02(18) . . ? C8B C7B C6B 108.95(18) . . ? C7B C8B C9B 109.51(16) . . ? C7B C8B C10B 110.25(18) . . ? C9B C8B C10B 108.56(18) . . ? C8B C9B C4B 110.43(16) . . ? C12B C10B C8B 109.27(16) . . ? C6B C11B C12B 109.26(18) . . ? C10B C12B C11B 109.9(2) . . ? C10B C12B C13B 110.21(18) . . ? C11B C12B C13B 108.67(17) . . ? C4B C13B C12B 109.74(17) . . ? N2B C14B C19B 109.92(16) . . ? N2B C14B C20B 109.26(15) . . ? C19B C14B C20B 108.93(17) . . ? N2B C14B C15B 109.71(15) . . ? C19B C14B C15B 108.84(15) . . ? C20B C14B C15B 110.17(16) . . ? C16B C15B C14B 109.35(16) . . ? C17B C16B C22B 110.73(19) . . ? C17B C16B C15B 109.25(19) . . ? C22B C16B C15B 109.08(18) . . ? C16B C17B C18B 109.35(17) . . ? C23B C18B C19B 109.76(17) . . ? C23B C18B C17B 109.27(19) . . ? C19B C18B C17B 109.42(17) . . ? C14B C19B C18B 109.66(17) . . ? C21B C20B C14B 109.35(16) . . ? C23B C21B C20B 109.72(18) . . ? C23B C21B C22B 109.62(18) . . ? C20B C21B C22B 108.75(17) . . ? C16B C22B C21B 109.49(18) . . ? C18B C23B C21B 109.69(18) . . ? N1A C1A N2A 105.44(13) . . ? N1A C1A Cu1B 127.71(13) . . ? N2A C1A Cu1B 126.78(14) . . ? C1A N1A C2A 110.65(16) . . ? C1A N1A C4A 123.69(13) . . ? C2A N1A C4A 125.53(15) . . ? C1A Cu1B Cl1B 178.31(7) . . ? C3A C2A N1A 106.63(16) . . ? C1A N2A C3A 109.87(16) . . ? C1A N2A C14A 123.24(13) . . ? C3A N2A C14A 126.88(15) . . ? C2A C3A N2A 107.40(15) . . ? N1A C4A C11A 110.71(13) . . ? N1A C4A C5A 108.23(16) . . ? C11A C4A C5A 109.41(16) . . ? N1A C4A C13A 109.35(15) . . ? C11A C4A C13A 108.36(16) . . ? C5A C4A C13A 110.78(14) . . ? C6A C5A C4A 109.41(17) . . ? C5A C6A C12A 109.04(15) . . ? C5A C6A C7A 108.88(17) . . ? C12A C6A C7A 110.18(18) . . ? C8A C7A C6A 109.73(15) . . ? C7A C8A C13A 109.19(18) . . ? C7A C8A C9A 109.88(17) . . ? C13A C8A C9A 109.42(15) . . ? C10A C9A C8A 108.76(18) . . ? C12A C10A C9A 109.38(16) . . ? C12A C10A C11A 109.34(19) . . ? C9A C10A C11A 110.38(17) . . ? C4A C11A C10A 109.13(14) . . ? C10A C12A C6A 109.48(17) . . ? C8A C13A C4A 109.67(16) . . ? N2A C14A C19A 111.06(14) . . ? N2A C14A C15A 109.27(15) . . ? C19A C14A C15A 108.59(18) . . ? N2A C14A C20A 108.94(17) . . ? C19A C14A C20A 108.56(15) . . ? C15A C14A C20A 110.43(14) . . ? C16A C15A C14A 110.23(16) . . ? C17A C16A C15A 109.41(17) . . ? C17A C16A C23A 109.82(19) . . ? C15A C16A C23A 108.9(2) . . ? C16A C17A C18A 109.6(2) . . ? C17A C18A C22A 109.57(17) . . ? C17A C18A C19A 110.41(18) . . ? C22A C18A C19A 108.8(2) . . ? C14A C19A C18A 109.31(15) . . ? C21A C20A C14A 109.30(18) . . ? C20A C21A C23A 109.15(17) . . ? C20A C21A C22A 109.34(15) . . ? C23A C21A C22A 110.0(2) . . ? C18A C22A C21A 109.20(17) . . ? C21A C23A C16A 109.76(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl1A Cu1A C1B N2B -153.9(12) . . . . ? Cl1A Cu1A C1B N1B 25.9(14) . . . . ? N2B C1B N1B C2B -0.38(19) . . . . ? Cu1A C1B N1B C2B 179.84(13) . . . . ? N2B C1B N1B C4B 178.06(15) . . . . ? Cu1A C1B N1B C4B -1.7(2) . . . . ? C1B N1B C2B C3B 0.6(2) . . . . ? C4B N1B C2B C3B -177.85(16) . . . . ? N1B C1B N2B C3B 0.0(2) . . . . ? Cu1A C1B N2B C3B 179.82(13) . . . . ? N1B C1B N2B C14B -178.36(15) . . . . ? Cu1A C1B N2B C14B 1.4(3) . . . . ? N1B C2B C3B N2B -0.5(2) . . . . ? C1B N2B C3B C2B 0.3(2) . . . . ? C14B N2B C3B C2B 178.71(16) . . . . ? C1B N1B C4B C5B 70.0(2) . . . . ? C2B N1B C4B C5B -111.8(2) . . . . ? C1B N1B C4B C13B -170.59(16) . . . . ? C2B N1B C4B C13B 7.6(2) . . . . ? C1B N1B C4B C9B -50.6(2) . . . . ? C2B N1B C4B C9B 127.64(18) . . . . ? N1B C4B C5B C6B -179.56(17) . . . . ? C13B C4B C5B C6B 60.3(2) . . . . ? C9B C4B C5B C6B -58.8(2) . . . . ? C4B C5B C6B C11B -60.4(2) . . . . ? C4B C5B C6B C7B 60.3(2) . . . . ? C11B C6B C7B C8B 60.1(2) . . . . ? C5B C6B C7B C8B -60.8(2) . . . . ? C6B C7B C8B C9B 59.9(2) . . . . ? C6B C7B C8B C10B -59.5(2) . . . . ? C7B C8B C9B C4B -59.7(2) . . . . ? C10B C8B C9B C4B 60.8(2) . . . . ? N1B C4B C9B C8B 179.97(14) . . . . ? C5B C4B C9B C8B 59.10(19) . . . . ? C13B C4B C9B C8B -59.7(2) . . . . ? C7B C8B C10B C12B 59.3(2) . . . . ? C9B C8B C10B C12B -60.6(2) . . . . ? C7B C6B C11B C12B -60.5(2) . . . . ? C5B C6B C11B C12B 60.4(2) . . . . ? C8B C10B C12B C11B -59.4(2) . . . . ? C8B C10B C12B C13B 60.4(2) . . . . ? C6B C11B C12B C10B 60.4(2) . . . . ? C6B C11B C12B C13B -60.3(2) . . . . ? N1B C4B C13B C12B 178.36(16) . . . . ? C5B C4B C13B C12B -61.4(2) . . . . ? C9B C4B C13B C12B 58.0(2) . . . . ? C10B C12B C13B C4B -59.2(2) . . . . ? C11B C12B C13B C4B 61.3(2) . . . . ? C1B N2B C14B C19B -176.98(16) . . . . ? C3B N2B C14B C19B 4.8(2) . . . . ? C1B N2B C14B C20B 63.5(2) . . . . ? C3B N2B C14B C20B -114.7(2) . . . . ? C1B N2B C14B C15B -57.3(2) . . . . ? C3B N2B C14B C15B 124.47(19) . . . . ? N2B C14B C15B C16B 179.21(18) . . . . ? C19B C14B C15B C16B -60.5(2) . . . . ? C20B C14B C15B C16B 58.9(2) . . . . ? C14B C15B C16B C17B 61.2(2) . . . . ? C14B C15B C16B C22B -60.0(2) . . . . ? C22B C16B C17B C18B 59.4(2) . . . . ? C15B C16B C17B C18B -60.7(2) . . . . ? C16B C17B C18B C23B -60.1(2) . . . . ? C16B C17B C18B C19B 60.1(3) . . . . ? N2B C14B C19B C18B -179.86(15) . . . . ? C20B C14B C19B C18B -60.17(19) . . . . ? C15B C14B C19B C18B 60.0(2) . . . . ? C23B C18B C19B C14B 60.1(2) . . . . ? C17B C18B C19B C14B -59.8(2) . . . . ? N2B C14B C20B C21B -179.73(16) . . . . ? C19B C14B C20B C21B 60.18(19) . . . . ? C15B C14B C20B C21B -59.1(2) . . . . ? C14B C20B C21B C23B -60.0(2) . . . . ? C14B C20B C21B C22B 59.9(2) . . . . ? C17B C16B C22B C21B -58.5(2) . . . . ? C15B C16B C22B C21B 61.7(2) . . . . ? C23B C21B C22B C16B 58.2(2) . . . . ? C20B C21B C22B C16B -61.8(2) . . . . ? C19B C18B C23B C21B -59.4(2) . . . . ? C17B C18B C23B C21B 60.6(2) . . . . ? C20B C21B C23B C18B 59.5(2) . . . . ? C22B C21B C23B C18B -59.8(2) . . . . ? N2A C1A N1A C2A -0.8(2) . . . . ? Cu1B C1A N1A C2A 176.31(16) . . . . ? N2A C1A N1A C4A -176.98(17) . . . . ? Cu1B C1A N1A C4A 0.1(3) . . . . ? N1A C1A Cu1B Cl1B -126.5(18) . . . . ? N2A C1A Cu1B Cl1B 50(2) . . . . ? C1A N1A C2A C3A 1.1(2) . . . . ? C4A N1A C2A C3A 177.19(19) . . . . ? N1A C1A N2A C3A 0.2(2) . . . . ? Cu1B C1A N2A C3A -176.93(15) . . . . ? N1A C1A N2A C14A -179.59(17) . . . . ? Cu1B C1A N2A C14A 3.2(3) . . . . ? N1A C2A C3A N2A -0.9(2) . . . . ? C1A N2A C3A C2A 0.4(2) . . . . ? C14A N2A C3A C2A -179.74(19) . . . . ? C1A N1A C4A C11A -172.84(18) . . . . ? C2A N1A C4A C11A 11.6(3) . . . . ? C1A N1A C4A C5A 67.3(2) . . . . ? C2A N1A C4A C5A -108.3(2) . . . . ? C1A N1A C4A C13A -53.5(2) . . . . ? C2A N1A C4A C13A 130.90(19) . . . . ? N1A C4A C5A C6A -178.48(14) . . . . ? C11A C4A C5A C6A 60.80(19) . . . . ? C13A C4A C5A C6A -58.6(2) . . . . ? C4A C5A C6A C12A -60.6(2) . . . . ? C4A C5A C6A C7A 59.63(19) . . . . ? C5A C6A C7A C8A -61.5(2) . . . . ? C12A C6A C7A C8A 58.0(2) . . . . ? C6A C7A C8A C13A 61.1(2) . . . . ? C6A C7A C8A C9A -58.9(2) . . . . ? C7A C8A C9A C10A 60.6(2) . . . . ? C13A C8A C9A C10A -59.3(2) . . . . ? C8A C9A C10A C12A -61.3(2) . . . . ? C8A C9A C10A C11A 59.0(2) . . . . ? N1A C4A C11A C10A -179.40(16) . . . . ? C5A C4A C11A C10A -60.2(2) . . . . ? C13A C4A C11A C10A 60.7(2) . . . . ? C12A C10A C11A C4A 60.0(2) . . . . ? C9A C10A C11A C4A -60.3(2) . . . . ? C9A C10A C12A C6A 60.7(2) . . . . ? C11A C10A C12A C6A -60.3(2) . . . . ? C5A C6A C12A C10A 60.5(2) . . . . ? C7A C6A C12A C10A -58.9(2) . . . . ? C7A C8A C13A C4A -58.85(19) . . . . ? C9A C8A C13A C4A 61.4(2) . . . . ? N1A C4A C13A C8A 177.36(15) . . . . ? C11A C4A C13A C8A -61.87(19) . . . . ? C5A C4A C13A C8A 58.2(2) . . . . ? C1A N2A C14A C19A -179.30(19) . . . . ? C3A N2A C14A C19A 0.9(3) . . . . ? C1A N2A C14A C15A -59.5(2) . . . . ? C3A N2A C14A C15A 120.7(2) . . . . ? C1A N2A C14A C20A 61.2(2) . . . . ? C3A N2A C14A C20A -118.6(2) . . . . ? N2A C14A C15A C16A 178.02(16) . . . . ? C19A C14A C15A C16A -60.7(2) . . . . ? C20A C14A C15A C16A 58.2(2) . . . . ? C14A C15A C16A C17A 61.0(2) . . . . ? C14A C15A C16A C23A -59.1(2) . . . . ? C15A C16A C17A C18A -59.4(2) . . . . ? C23A C16A C17A C18A 60.0(2) . . . . ? C16A C17A C18A C22A -60.9(2) . . . . ? C16A C17A C18A C19A 59.0(2) . . . . ? N2A C14A C19A C18A 179.20(17) . . . . ? C15A C14A C19A C18A 59.0(2) . . . . ? C20A C14A C19A C18A -61.1(2) . . . . ? C17A C18A C19A C14A -59.0(2) . . . . ? C22A C18A C19A C14A 61.3(2) . . . . ? N2A C14A C20A C21A -178.11(13) . . . . ? C19A C14A C20A C21A 60.8(2) . . . . ? C15A C14A C20A C21A -58.11(19) . . . . ? C14A C20A C21A C23A 59.5(2) . . . . ? C14A C20A C21A C22A -60.8(2) . . . . ? C17A C18A C22A C21A 60.1(2) . . . . ? C19A C18A C22A C21A -60.7(2) . . . . ? C20A C21A C22A C18A 60.8(2) . . . . ? C23A C21A C22A C18A -59.0(2) . . . . ? C20A C21A C23A C16A -61.6(2) . . . . ? C22A C21A C23A C16A 58.3(2) . . . . ? C17A C16A C23A C21A -58.8(3) . . . . ? C15A C16A C23A C21A 61.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 37.07 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.667 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.085 # Attachment '- 3b-CCDC750318.txt' data_sd018pna21 _database_code_depnum_ccdc_archive 'CCDC 750318' #TrackingRef '- 3b-CCDC750318.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 Br Cu N2' _chemical_formula_weight 479.96 _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' 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 11.5621(5) _cell_length_b 26.7715(12) _cell_length_c 6.4838(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2006.96(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8107 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 35.20 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 3.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5200 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; SADABS Version 2008/1 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_suppport 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_reflns_number 22474 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 36.37 _reflns_number_total 6889 _reflns_number_gt 6059 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2008.6-1' _computing_cell_refinement 'Bruker APEX2 v2008.6-1' _computing_data_reduction 'Bruker SAINT V7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _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. This structure refined as a racemic twin (basf 0.22). ; _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^)+(0.0604P)^2^+20.9496P] 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 noref _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 0.22(3) _refine_ls_number_reflns 6889 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2223 _refine_ls_wR_factor_gt 0.2173 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.47932(6) -0.15239(3) 0.50922(15) 0.02061(16) Uani 1 1 d . . . Cu1 Cu -0.37013(7) -0.16094(3) 0.22631(14) 0.01218(15) Uani 1 1 d . . . C1 C -0.2805(5) -0.1652(2) -0.0209(10) 0.0093(10) Uani 1 1 d . . . N1 N -0.2525(4) -0.20625(19) -0.1309(9) 0.0094(8) Uani 1 1 d . . . N2 N -0.2371(4) -0.12609(19) -0.1316(9) 0.0092(8) Uani 1 1 d . . . C2 C -0.1908(5) -0.1939(2) -0.3067(10) 0.0107(10) Uani 1 1 d . . . H2 H -0.1603 -0.2163 -0.4065 0.013 Uiso 1 1 calc R . . C3 C -0.1826(5) -0.1430(2) -0.3075(10) 0.0111(10) Uani 1 1 d . . . H3 H -0.1462 -0.1230 -0.4098 0.013 Uiso 1 1 calc R . . C4 C -0.2820(5) -0.2584(2) -0.0673(11) 0.0099(10) Uani 1 1 d . . . C5 C -0.2267(5) -0.2711(2) 0.1401(11) 0.0123(10) Uani 1 1 d . . . H5A H -0.2556 -0.2479 0.2473 0.015 Uiso 1 1 calc R . . H5B H -0.1417 -0.2672 0.1307 0.015 Uiso 1 1 calc R . . C6 C -0.2563(6) -0.3251(3) 0.2002(12) 0.0154(12) Uani 1 1 d . . . H6 H -0.2203 -0.3331 0.3365 0.018 Uiso 1 1 calc R . . C7 C -0.2085(6) -0.3608(2) 0.0355(12) 0.0150(12) Uani 1 1 d . . . H7A H -0.2259 -0.3958 0.0737 0.018 Uiso 1 1 calc R . . H7B H -0.1235 -0.3570 0.0251 0.018 Uiso 1 1 calc R . . C8 C -0.2658(6) -0.3480(2) -0.1742(12) 0.0142(11) Uani 1 1 d . . . H8 H -0.2354 -0.3711 -0.2826 0.017 Uiso 1 1 calc R . . C9 C -0.3970(5) -0.3542(3) -0.1576(13) 0.0157(12) Uani 1 1 d . . . H9A H -0.4162 -0.3892 -0.1214 0.019 Uiso 1 1 calc R . . H9B H -0.4339 -0.3462 -0.2915 0.019 Uiso 1 1 calc R . . C10 C -0.4423(5) -0.3186(2) 0.0105(14) 0.0139(10) Uani 1 1 d . . . H10 H -0.5279 -0.3226 0.0247 0.017 Uiso 1 1 calc R . . C11 C -0.4140(5) -0.2644(2) -0.0535(11) 0.0112(10) Uani 1 1 d . . . H11A H -0.4496 -0.2569 -0.1889 0.013 Uiso 1 1 calc R . . H11B H -0.4457 -0.2408 0.0494 0.013 Uiso 1 1 calc R . . C12 C -0.2375(5) -0.2947(2) -0.2329(11) 0.0129(11) Uani 1 1 d . . . H12A H -0.2738 -0.2866 -0.3671 0.015 Uiso 1 1 calc R . . H12B H -0.1527 -0.2909 -0.2479 0.015 Uiso 1 1 calc R . . C13 C -0.3841(7) -0.3294(3) 0.2170(17) 0.0241(15) Uani 1 1 d . . . H13A H -0.4127 -0.3055 0.3216 0.029 Uiso 1 1 calc R . . H13B H -0.4047 -0.3635 0.2630 0.029 Uiso 1 1 calc R . . C14 C -0.2458(5) -0.0730(2) -0.0682(11) 0.0105(10) Uani 1 1 d . . . C15 C -0.1814(6) -0.0646(2) 0.1359(11) 0.0119(10) Uani 1 1 d . . . H15A H -0.2162 -0.0856 0.2451 0.014 Uiso 1 1 calc R . . H15B H -0.0994 -0.0745 0.1201 0.014 Uiso 1 1 calc R . . C16 C -0.1884(6) -0.0098(2) 0.1984(12) 0.0153(11) Uani 1 1 d . . . H16 H -0.1463 -0.0047 0.3316 0.018 Uiso 1 1 calc R . . C17 C -0.1338(6) 0.0227(3) 0.0319(13) 0.0180(12) Uani 1 1 d . . . H17A H -0.0515 0.0135 0.0141 0.022 Uiso 1 1 calc R . . H17B H -0.1376 0.0583 0.0730 0.022 Uiso 1 1 calc R . . C18 C -0.1989(6) 0.0150(3) -0.1717(12) 0.0161(12) Uani 1 1 d . . . H18 H -0.1628 0.0362 -0.2811 0.019 Uiso 1 1 calc R . . C19 C -0.3260(7) 0.0305(3) -0.1438(13) 0.0183(13) Uani 1 1 d . . . H19A H -0.3303 0.0660 -0.1021 0.022 Uiso 1 1 calc R . . H19B H -0.3680 0.0265 -0.2758 0.022 Uiso 1 1 calc R . . C20 C -0.3819(5) -0.0024(2) 0.0220(14) 0.0146(11) Uani 1 1 d . . . H20 H -0.4650 0.0072 0.0388 0.018 Uiso 1 1 calc R . . C21 C -0.3740(5) -0.0573(2) -0.0443(12) 0.0132(10) Uani 1 1 d . . . H21A H -0.4149 -0.0620 -0.1771 0.016 Uiso 1 1 calc R . . H21B H -0.4119 -0.0787 0.0603 0.016 Uiso 1 1 calc R . . C22 C -0.1912(5) -0.0401(2) -0.2352(11) 0.0128(11) Uani 1 1 d . . . H22A H -0.2321 -0.0452 -0.3677 0.015 Uiso 1 1 calc R . . H22B H -0.1091 -0.0496 -0.2546 0.015 Uiso 1 1 calc R . . C23 C -0.3186(6) 0.0044(2) 0.2270(13) 0.0166(11) Uani 1 1 d . . . H23A H -0.3540 -0.0172 0.3336 0.020 Uiso 1 1 calc R . . H23B H -0.3250 0.0396 0.2730 0.020 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 0.0121(2) 0.0396(4) 0.0102(3) 0.0003(3) 0.0033(2) -0.0003(2) Cu1 0.0115(3) 0.0160(3) 0.0090(3) 0.0001(3) 0.0039(3) -0.0003(2) C1 0.014(2) 0.008(2) 0.006(3) 0.0011(17) -0.0038(17) 0.0009(17) N1 0.0072(18) 0.011(2) 0.010(2) -0.0003(17) 0.0029(16) -0.0009(15) N2 0.0090(18) 0.011(2) 0.007(2) 0.0009(17) 0.0010(15) -0.0008(16) C2 0.0097(19) 0.018(2) 0.005(3) -0.0024(19) 0.0019(17) -0.0005(18) C3 0.0076(19) 0.020(2) 0.006(3) 0.002(2) 0.0016(17) -0.0003(18) C4 0.0040(17) 0.014(2) 0.012(3) -0.001(2) -0.0015(17) -0.0036(17) C5 0.013(2) 0.013(2) 0.010(3) 0.000(2) -0.0032(19) 0.0026(19) C6 0.017(2) 0.019(3) 0.010(3) 0.002(2) -0.004(2) -0.001(2) C7 0.017(2) 0.015(2) 0.013(3) 0.002(2) -0.002(2) 0.002(2) C8 0.013(2) 0.015(3) 0.015(3) -0.001(2) 0.003(2) -0.001(2) C9 0.009(2) 0.019(3) 0.019(3) -0.005(2) -0.001(2) -0.001(2) C10 0.0088(18) 0.019(3) 0.014(3) 0.000(3) 0.002(2) -0.0022(18) C11 0.009(2) 0.009(2) 0.015(3) 0.002(2) 0.0011(19) 0.0014(17) C12 0.010(2) 0.018(2) 0.011(3) -0.001(2) -0.0004(18) 0.0037(19) C13 0.036(4) 0.017(3) 0.019(4) 0.005(3) 0.001(3) -0.011(3) C14 0.014(2) 0.009(2) 0.009(3) 0.0015(19) 0.0015(19) 0.0004(18) C15 0.016(2) 0.012(2) 0.008(3) 0.0003(19) -0.002(2) -0.002(2) C16 0.018(2) 0.018(3) 0.010(3) 0.001(2) 0.000(2) -0.004(2) C17 0.018(2) 0.019(3) 0.017(3) -0.001(3) 0.004(3) -0.006(2) C18 0.022(3) 0.015(3) 0.011(3) -0.001(2) 0.007(2) -0.003(2) C19 0.022(3) 0.019(3) 0.015(3) 0.004(2) 0.001(2) 0.001(2) C20 0.014(2) 0.013(2) 0.017(3) 0.001(2) 0.003(2) 0.0012(18) C21 0.010(2) 0.015(2) 0.015(3) 0.001(2) -0.0006(19) -0.0018(19) C22 0.015(2) 0.012(2) 0.011(3) 0.0023(19) 0.0022(19) 0.0001(19) C23 0.023(3) 0.016(2) 0.011(3) -0.005(3) 0.004(3) 0.003(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 Br1 Cu1 2.2386(12) . ? Cu1 C1 1.912(6) . ? C1 N1 1.350(8) . ? C1 N2 1.365(8) . ? N1 C2 1.385(8) . ? N1 C4 1.495(8) . ? N2 C3 1.379(8) . ? N2 C14 1.484(8) . ? C2 C3 1.367(9) . ? C4 C5 1.528(9) . ? C4 C12 1.536(9) . ? C4 C11 1.538(8) . ? C5 C6 1.536(10) . ? C6 C13 1.486(11) . ? C6 C7 1.535(11) . ? C7 C8 1.550(11) . ? C8 C12 1.512(9) . ? C8 C9 1.531(9) . ? C9 C10 1.539(11) . ? C10 C13 1.526(13) . ? C10 C11 1.546(9) . ? C14 C22 1.532(9) . ? C14 C15 1.535(9) . ? C14 C21 1.548(8) . ? C15 C16 1.525(9) . ? C16 C17 1.523(10) . ? C16 C23 1.563(10) . ? C17 C18 1.533(11) . ? C18 C22 1.535(9) . ? C18 C19 1.537(10) . ? C19 C20 1.532(11) . ? C20 C23 1.529(12) . ? C20 C21 1.535(9) . ? 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 Br1 177.02(17) . . ? N1 C1 N2 105.0(5) . . ? N1 C1 Cu1 128.4(4) . . ? N2 C1 Cu1 126.5(4) . . ? C1 N1 C2 111.3(5) . . ? C1 N1 C4 124.1(5) . . ? C2 N1 C4 124.6(5) . . ? C1 N2 C3 110.6(5) . . ? C1 N2 C14 124.3(5) . . ? C3 N2 C14 125.0(5) . . ? C3 C2 N1 106.1(5) . . ? C2 C3 N2 106.9(5) . . ? N1 C4 C5 110.8(5) . . ? N1 C4 C12 108.8(5) . . ? C5 C4 C12 109.5(5) . . ? N1 C4 C11 109.8(5) . . ? C5 C4 C11 110.0(5) . . ? C12 C4 C11 107.9(5) . . ? C4 C5 C6 109.8(5) . . ? C13 C6 C7 111.2(6) . . ? C13 C6 C5 108.2(5) . . ? C7 C6 C5 109.2(6) . . ? C6 C7 C8 108.6(5) . . ? C12 C8 C9 109.5(5) . . ? C12 C8 C7 109.7(6) . . ? C9 C8 C7 109.8(6) . . ? C8 C9 C10 108.6(5) . . ? C13 C10 C9 110.8(6) . . ? C13 C10 C11 108.6(6) . . ? C9 C10 C11 108.6(6) . . ? C4 C11 C10 108.9(5) . . ? C8 C12 C4 110.4(6) . . ? C6 C13 C10 111.1(7) . . ? N2 C14 C22 109.1(5) . . ? N2 C14 C15 110.2(5) . . ? C22 C14 C15 109.0(5) . . ? N2 C14 C21 110.6(5) . . ? C22 C14 C21 108.1(5) . . ? C15 C14 C21 109.8(5) . . ? C16 C15 C14 110.1(5) . . ? C17 C16 C15 109.8(6) . . ? C17 C16 C23 110.2(6) . . ? C15 C16 C23 108.4(5) . . ? C16 C17 C18 109.3(5) . . ? C17 C18 C22 109.3(6) . . ? C17 C18 C19 109.4(6) . . ? C22 C18 C19 110.2(6) . . ? C20 C19 C18 109.4(6) . . ? C23 C20 C19 109.8(6) . . ? C23 C20 C21 109.2(5) . . ? C19 C20 C21 109.2(6) . . ? C20 C21 C14 110.1(5) . . ? C14 C22 C18 109.8(5) . . ? C20 C23 C16 109.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Cu1 C1 N1 -140(3) . . . . ? Br1 Cu1 C1 N2 35(4) . . . . ? N2 C1 N1 C2 1.0(7) . . . . ? Cu1 C1 N1 C2 177.1(4) . . . . ? N2 C1 N1 C4 179.5(5) . . . . ? Cu1 C1 N1 C4 -4.3(9) . . . . ? N1 C1 N2 C3 -0.2(7) . . . . ? Cu1 C1 N2 C3 -176.5(4) . . . . ? N1 C1 N2 C14 -179.2(5) . . . . ? Cu1 C1 N2 C14 4.6(8) . . . . ? C1 N1 C2 C3 -1.4(7) . . . . ? C4 N1 C2 C3 -179.9(5) . . . . ? N1 C2 C3 N2 1.2(7) . . . . ? C1 N2 C3 C2 -0.6(7) . . . . ? C14 N2 C3 C2 178.3(5) . . . . ? C1 N1 C4 C5 -60.4(7) . . . . ? C2 N1 C4 C5 117.9(6) . . . . ? C1 N1 C4 C12 179.2(5) . . . . ? C2 N1 C4 C12 -2.5(7) . . . . ? C1 N1 C4 C11 61.3(8) . . . . ? C2 N1 C4 C11 -120.4(6) . . . . ? N1 C4 C5 C6 -179.0(5) . . . . ? C12 C4 C5 C6 -59.0(6) . . . . ? C11 C4 C5 C6 59.4(7) . . . . ? C4 C5 C6 C13 -60.5(8) . . . . ? C4 C5 C6 C7 60.7(7) . . . . ? C13 C6 C7 C8 58.7(8) . . . . ? C5 C6 C7 C8 -60.6(7) . . . . ? C6 C7 C8 C12 60.4(7) . . . . ? C6 C7 C8 C9 -60.0(7) . . . . ? C12 C8 C9 C10 -60.6(8) . . . . ? C7 C8 C9 C10 59.9(7) . . . . ? C8 C9 C10 C13 -58.1(7) . . . . ? C8 C9 C10 C11 61.2(7) . . . . ? N1 C4 C11 C10 179.5(6) . . . . ? C5 C4 C11 C10 -58.3(7) . . . . ? C12 C4 C11 C10 61.1(7) . . . . ? C13 C10 C11 C4 58.3(8) . . . . ? C9 C10 C11 C4 -62.2(7) . . . . ? C9 C8 C12 C4 61.0(7) . . . . ? C7 C8 C12 C4 -59.5(6) . . . . ? N1 C4 C12 C8 -180.0(5) . . . . ? C5 C4 C12 C8 58.8(6) . . . . ? C11 C4 C12 C8 -60.9(7) . . . . ? C7 C6 C13 C10 -57.8(8) . . . . ? C5 C6 C13 C10 62.2(8) . . . . ? C9 C10 C13 C6 57.4(7) . . . . ? C11 C10 C13 C6 -61.8(8) . . . . ? C1 N2 C14 C22 -177.9(5) . . . . ? C3 N2 C14 C22 3.3(8) . . . . ? C1 N2 C14 C15 62.5(7) . . . . ? C3 N2 C14 C15 -116.3(6) . . . . ? C1 N2 C14 C21 -59.2(8) . . . . ? C3 N2 C14 C21 122.1(6) . . . . ? N2 C14 C15 C16 178.8(5) . . . . ? C22 C14 C15 C16 59.1(7) . . . . ? C21 C14 C15 C16 -59.1(7) . . . . ? C14 C15 C16 C17 -59.9(7) . . . . ? C14 C15 C16 C23 60.5(7) . . . . ? C15 C16 C17 C18 60.0(7) . . . . ? C23 C16 C17 C18 -59.3(7) . . . . ? C16 C17 C18 C22 -60.1(7) . . . . ? C16 C17 C18 C19 60.7(7) . . . . ? C17 C18 C19 C20 -61.1(8) . . . . ? C22 C18 C19 C20 59.2(8) . . . . ? C18 C19 C20 C23 60.5(8) . . . . ? C18 C19 C20 C21 -59.2(8) . . . . ? C23 C20 C21 C14 -59.3(7) . . . . ? C19 C20 C21 C14 60.8(8) . . . . ? N2 C14 C21 C20 179.8(6) . . . . ? C22 C14 C21 C20 -60.8(7) . . . . ? C15 C14 C21 C20 57.9(7) . . . . ? N2 C14 C22 C18 -179.7(5) . . . . ? C15 C14 C22 C18 -59.3(7) . . . . ? C21 C14 C22 C18 60.0(7) . . . . ? C17 C18 C22 C14 60.2(7) . . . . ? C19 C18 C22 C14 -60.1(7) . . . . ? C19 C20 C23 C16 -58.6(7) . . . . ? C21 C20 C23 C16 61.1(7) . . . . ? C17 C16 C23 C20 58.5(7) . . . . ? C15 C16 C23 C20 -61.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 36.37 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 3.148 _refine_diff_density_min -2.515 _refine_diff_density_rms 0.238 # Attachment '- 3c-CCDC750319.txt' data_sd019cp-1 _database_code_depnum_ccdc_archive 'CCDC 750319' #TrackingRef '- 3c-CCDC750319.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H64 Cu2 I2 N4' _chemical_formula_weight 1053.89 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 9.6305(2) _cell_length_b 9.9465(2) _cell_length_c 11.4681(3) _cell_angle_alpha 73.5890(10) _cell_angle_beta 81.0420(10) _cell_angle_gamma 88.3730(10) _cell_volume 1040.78(4) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8795 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 39.54 _exptl_crystal_description BLOCK _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 2.543 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3629 _exptl_absorpt_correction_T_max 0.4294 _exptl_absorpt_process_details ; SADABS Version 2.1 2003 Bruker-Nonius Blessing, Acta Cryst. (1995) A51 33-38 ; _exptl_special_details ; It should be noted that the esd's of the cell dimensions are probably too low; they should be multiplied by a factor of 2 to 10 ; _diffrn_ambient_temperature 100(2) _diffrn_measurement_specimen_support 'magnetic support whith 10 micron nylon fiber cryoloop' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'rotating anode X-ray tube' _diffrn_source_type 'Bruker-Nonius FR 591' _diffrn_source_power 50 _diffrn_source_current 70 _diffrn_source_size '3 mm x 0.3 mm fine focus' _diffrn_radiation_monochromator 'Multilayer Montel 200 mirrors' _diffrn_detector_type '4K CCD area detector APEX II' _diffrn_measurement_device_type 'Kappa 4-axis goniometer bruker-nonius' _diffrn_measurement_method ; Fullsphere data collection, phi and omega scans ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25425 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 39.91 _reflns_number_total 10904 _reflns_number_gt 10109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius Apex v1.0-22 2002' _computing_cell_refinement 'Bruker-Nonius Apex v1.0-22 2002' _computing_data_reduction 'SAINT+ Version 7.06A Bruker-Nonius, 2004' _computing_structure_solution 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'Shelxtl Version 6.12 (Sheldrick, 2001)' _computing_publication_material 'Shelxtl Version 6.12 (Sheldrick, 2001)' _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^)+(0.0408P)^2^+0.5821P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10904 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.004 _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 0.634322(8) 0.832294(8) 0.568170(7) 0.01826(3) Uani 1 1 d . . . N1 N 0.11376(11) 0.75130(10) 0.56341(8) 0.01300(14) Uani 1 1 d . . . C1 C 0.24076(12) 0.77886(11) 0.48934(9) 0.01284(15) Uani 1 1 d . . . Cu2 Cu 0.394623(18) 0.894523(17) 0.501353(14) 0.01708(3) Uani 1 1 d . . . N2 N 0.22742(11) 0.72813(10) 0.39268(8) 0.01275(14) Uani 1 1 d . . . C2 C 0.02242(14) 0.68825(15) 0.51211(12) 0.0199(2) Uani 1 1 d . . . H2 H -0.0706 0.6616 0.5446 0.024 Uiso 1 1 calc R . . C3 C 0.09427(14) 0.67272(14) 0.40570(11) 0.01869(19) Uani 1 1 d . . . H3 H 0.0604 0.6324 0.3516 0.022 Uiso 1 1 calc R . . C4 C 0.07568(12) 0.78520(11) 0.68272(9) 0.01240(15) Uani 1 1 d . . . C5 C -0.03742(14) 0.68061(11) 0.76618(10) 0.01635(18) Uani 1 1 d . . . H5A H -0.0018 0.5860 0.7806 0.020 Uiso 1 1 calc R . . H5B H -0.1198 0.6856 0.7261 0.020 Uiso 1 1 calc R . . C6 C -0.07802(14) 0.71503(12) 0.88967(10) 0.01684(18) Uani 1 1 d . . . H6 H -0.1508 0.6485 0.9421 0.020 Uiso 1 1 calc R . . C7 C 0.05075(16) 0.70506(17) 0.95423(11) 0.0234(2) Uani 1 1 d . . . H7A H 0.0863 0.6104 0.9713 0.028 Uiso 1 1 calc R . . H7B H 0.0251 0.7274 1.0318 0.028 Uiso 1 1 calc R . . C8 C 0.16424(15) 0.80817(18) 0.87105(11) 0.0232(2) Uani 1 1 d . . . H8 H 0.2474 0.8016 0.9118 0.028 Uiso 1 1 calc R . . C9 C 0.20471(14) 0.77345(17) 0.74796(11) 0.0207(2) Uani 1 1 d . . . H9A H 0.2780 0.8379 0.6962 0.025 Uiso 1 1 calc R . . H9B H 0.2408 0.6791 0.7625 0.025 Uiso 1 1 calc R . . C10 C 0.01772(13) 0.93422(11) 0.65996(9) 0.01456(17) Uani 1 1 d . . . H10A H 0.0881 1.0010 0.6067 0.017 Uiso 1 1 calc R . . H10B H -0.0646 0.9411 0.6196 0.017 Uiso 1 1 calc R . . C11 C -0.02161(15) 0.96820(12) 0.78332(11) 0.0183(2) Uani 1 1 d . . . H11 H -0.0579 1.0636 0.7688 0.022 Uiso 1 1 calc R . . C12 C -0.13514(14) 0.86407(13) 0.86508(10) 0.01712(18) Uani 1 1 d . . . H12A H -0.2174 0.8705 0.8247 0.021 Uiso 1 1 calc R . . H12B H -0.1628 0.8865 0.9423 0.021 Uiso 1 1 calc R . . C13 C 0.10885(17) 0.95778(17) 0.84598(12) 0.0241(2) Uani 1 1 d . . . H13A H 0.0852 0.9821 0.9228 0.029 Uiso 1 1 calc R . . H13B H 0.1809 1.0231 0.7934 0.029 Uiso 1 1 calc R . . C14 C 0.34838(12) 0.71040(10) 0.30000(9) 0.01165(15) Uani 1 1 d . . . C15 C 0.29581(14) 0.66130(14) 0.19924(10) 0.01760(18) Uani 1 1 d . . . H15A H 0.2341 0.7309 0.1573 0.021 Uiso 1 1 calc R . . H15B H 0.2428 0.5741 0.2357 0.021 Uiso 1 1 calc R . . C16 C 0.42217(15) 0.63942(14) 0.10633(10) 0.0186(2) Uani 1 1 d . . . H16 H 0.3881 0.6080 0.0420 0.022 Uiso 1 1 calc R . . C17 C 0.50521(15) 0.77671(14) 0.04776(10) 0.0188(2) Uani 1 1 d . . . H17A H 0.4456 0.8475 0.0044 0.023 Uiso 1 1 calc R . . H17B H 0.5843 0.7629 -0.0110 0.023 Uiso 1 1 calc R . . C18 C 0.55796(14) 0.82530(12) 0.14878(10) 0.01615(18) Uani 1 1 d . . . H18 H 0.6112 0.9135 0.1116 0.019 Uiso 1 1 calc R . . C19 C 0.43095(13) 0.84866(11) 0.24016(10) 0.01462(17) Uani 1 1 d . . . H19A H 0.4632 0.8823 0.3031 0.018 Uiso 1 1 calc R . . H19B H 0.3705 0.9189 0.1973 0.018 Uiso 1 1 calc R . . C20 C 0.44428(14) 0.59879(11) 0.36601(9) 0.01506(17) Uani 1 1 d . . . H20A H 0.3919 0.5114 0.4035 0.018 Uiso 1 1 calc R . . H20B H 0.4773 0.6285 0.4307 0.018 Uiso 1 1 calc R . . C21 C 0.57053(15) 0.57600(13) 0.27415(10) 0.0185(2) Uani 1 1 d . . . H21 H 0.6314 0.5045 0.3171 0.022 Uiso 1 1 calc R . . C22 C 0.51847(17) 0.52778(13) 0.17276(11) 0.0216(2) Uani 1 1 d . . . H22A H 0.4672 0.4395 0.2084 0.026 Uiso 1 1 calc R . . H22B H 0.5980 0.5135 0.1145 0.026 Uiso 1 1 calc R . . C23 C 0.65307(14) 0.71422(14) 0.21720(11) 0.0187(2) Uani 1 1 d . . . H23A H 0.7345 0.7007 0.1604 0.022 Uiso 1 1 calc R . . H23B H 0.6858 0.7453 0.2813 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01446(4) 0.01502(3) 0.02536(4) -0.00439(2) -0.00569(3) 0.00034(2) N1 0.0111(4) 0.0161(3) 0.0131(3) -0.0072(3) -0.0004(3) 0.0006(3) C1 0.0123(4) 0.0143(3) 0.0127(3) -0.0055(3) -0.0014(3) 0.0008(3) Cu2 0.01517(7) 0.02176(6) 0.01597(6) -0.00879(5) -0.00034(5) -0.00281(5) N2 0.0125(4) 0.0144(3) 0.0125(3) -0.0061(2) -0.0011(3) 0.0001(3) C2 0.0128(5) 0.0304(6) 0.0197(4) -0.0136(4) 0.0009(4) -0.0039(4) C3 0.0148(5) 0.0266(5) 0.0183(4) -0.0128(4) -0.0008(3) -0.0031(4) C4 0.0114(4) 0.0148(3) 0.0114(3) -0.0050(3) -0.0008(3) 0.0015(3) C5 0.0193(5) 0.0137(4) 0.0145(4) -0.0031(3) 0.0005(3) -0.0009(3) C6 0.0185(5) 0.0177(4) 0.0118(4) -0.0018(3) 0.0009(3) 0.0000(3) C7 0.0233(6) 0.0326(6) 0.0122(4) -0.0028(4) -0.0045(4) 0.0072(5) C8 0.0148(5) 0.0432(7) 0.0148(4) -0.0126(4) -0.0037(4) 0.0022(5) C9 0.0130(5) 0.0362(6) 0.0159(4) -0.0117(4) -0.0039(3) 0.0062(4) C10 0.0170(5) 0.0133(3) 0.0122(3) -0.0036(3) 0.0010(3) 0.0005(3) C11 0.0231(6) 0.0156(4) 0.0157(4) -0.0067(3) 0.0027(4) 0.0002(4) C12 0.0153(5) 0.0203(4) 0.0146(4) -0.0057(3) 0.0019(3) 0.0020(4) C13 0.0230(6) 0.0340(6) 0.0191(5) -0.0161(4) 0.0035(4) -0.0092(5) C14 0.0130(4) 0.0115(3) 0.0107(3) -0.0043(2) -0.0007(3) 0.0013(3) C15 0.0178(5) 0.0236(5) 0.0135(4) -0.0090(3) -0.0009(3) -0.0029(4) C16 0.0220(6) 0.0233(5) 0.0124(4) -0.0090(3) 0.0002(3) -0.0017(4) C17 0.0214(6) 0.0220(4) 0.0109(4) -0.0023(3) -0.0003(3) 0.0015(4) C18 0.0162(5) 0.0158(4) 0.0145(4) -0.0032(3) 0.0015(3) -0.0004(3) C19 0.0165(5) 0.0109(3) 0.0154(4) -0.0036(3) 0.0003(3) 0.0011(3) C20 0.0201(5) 0.0127(3) 0.0112(3) -0.0027(3) -0.0008(3) 0.0048(3) C21 0.0226(6) 0.0177(4) 0.0140(4) -0.0045(3) -0.0008(3) 0.0095(4) C22 0.0310(7) 0.0166(4) 0.0171(4) -0.0084(3) 0.0027(4) 0.0037(4) C23 0.0146(5) 0.0257(5) 0.0159(4) -0.0074(3) -0.0004(3) 0.0042(4) _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 Cu2 2.5497(2) . ? I1 Cu2 2.62654(19) 2_676 ? N1 C1 1.3625(15) . ? N1 C2 1.3836(17) . ? N1 C4 1.4892(13) . ? C1 N2 1.3653(14) . ? C1 Cu2 1.9463(12) . ? Cu2 I1 2.62654(19) 2_676 ? Cu2 Cu2 2.9510(3) 2_676 ? N2 C3 1.3799(17) . ? N2 C14 1.4921(14) . ? C2 C3 1.3524(17) . ? C4 C9 1.5328(17) . ? C4 C10 1.5351(14) . ? C4 C5 1.5368(16) . ? C5 C6 1.5395(16) . ? C6 C7 1.528(2) . ? C6 C12 1.5315(16) . ? C7 C8 1.531(2) . ? C8 C13 1.531(2) . ? C8 C9 1.5364(17) . ? C10 C11 1.5347(15) . ? C11 C13 1.529(2) . ? C11 C12 1.5309(18) . ? C14 C20 1.5308(15) . ? C14 C15 1.5314(16) . ? C14 C19 1.5341(15) . ? C15 C16 1.5413(17) . ? C16 C17 1.5271(19) . ? C16 C22 1.5353(19) . ? C17 C18 1.5321(18) . ? C18 C23 1.5336(17) . ? C18 C19 1.5397(16) . ? C20 C21 1.5362(16) . ? C21 C23 1.530(2) . ? C21 C22 1.531(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 Cu2 I1 Cu2 69.498(7) . 2_676 ? C1 N1 C2 110.73(9) . . ? C1 N1 C4 125.40(10) . . ? C2 N1 C4 123.86(10) . . ? N1 C1 N2 104.60(10) . . ? N1 C1 Cu2 127.84(8) . . ? N2 C1 Cu2 126.68(8) . . ? C1 Cu2 I1 131.91(3) . . ? C1 Cu2 I1 117.56(3) . 2_676 ? I1 Cu2 I1 110.502(6) . 2_676 ? C1 Cu2 Cu2 171.44(3) . 2_676 ? I1 Cu2 Cu2 56.477(6) . 2_676 ? I1 Cu2 Cu2 54.024(6) 2_676 2_676 ? C1 N2 C3 110.74(9) . . ? C1 N2 C14 123.64(10) . . ? C3 N2 C14 124.62(9) . . ? C3 C2 N1 106.88(11) . . ? C2 C3 N2 107.02(11) . . ? N1 C4 C9 110.24(9) . . ? N1 C4 C10 109.70(8) . . ? C9 C4 C10 109.92(10) . . ? N1 C4 C5 109.42(9) . . ? C9 C4 C5 108.36(10) . . ? C10 C4 C5 109.17(9) . . ? C4 C5 C6 109.87(10) . . ? C7 C6 C12 109.58(12) . . ? C7 C6 C5 109.97(10) . . ? C12 C6 C5 108.89(9) . . ? C6 C7 C8 109.06(10) . . ? C13 C8 C7 109.81(11) . . ? C13 C8 C9 108.85(11) . . ? C7 C8 C9 110.01(13) . . ? C4 C9 C8 109.84(10) . . ? C11 C10 C4 109.38(9) . . ? C13 C11 C12 110.07(10) . . ? C13 C11 C10 109.43(10) . . ? C12 C11 C10 109.15(10) . . ? C11 C12 C6 109.56(10) . . ? C11 C13 C8 109.52(11) . . ? N2 C14 C20 108.00(8) . . ? N2 C14 C15 110.21(9) . . ? C20 C14 C15 109.05(9) . . ? N2 C14 C19 110.99(8) . . ? C20 C14 C19 109.82(10) . . ? C15 C14 C19 108.76(9) . . ? C14 C15 C16 109.57(10) . . ? C17 C16 C22 109.26(12) . . ? C17 C16 C15 109.98(10) . . ? C22 C16 C15 109.56(9) . . ? C16 C17 C18 109.09(9) . . ? C17 C18 C23 110.16(10) . . ? C17 C18 C19 109.13(11) . . ? C23 C18 C19 109.44(9) . . ? C14 C19 C18 109.60(8) . . ? C14 C20 C21 110.06(8) . . ? C23 C21 C22 109.58(10) . . ? C23 C21 C20 108.96(9) . . ? C22 C21 C20 109.63(12) . . ? C21 C22 C16 109.40(9) . . ? C21 C23 C18 109.41(11) . . ? 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 C2 N1 C1 N2 -1.58(12) . . . . ? C4 N1 C1 N2 179.17(9) . . . . ? C2 N1 C1 Cu2 168.17(9) . . . . ? C4 N1 C1 Cu2 -11.08(15) . . . . ? N1 C1 Cu2 I1 107.80(9) . . . . ? N2 C1 Cu2 I1 -84.60(10) . . . . ? N1 C1 Cu2 I1 -74.46(10) . . . 2_676 ? N2 C1 Cu2 I1 93.14(9) . . . 2_676 ? N1 C1 Cu2 Cu2 -84.3(2) . . . 2_676 ? N2 C1 Cu2 Cu2 83.3(2) . . . 2_676 ? Cu2 I1 Cu2 C1 177.86(4) 2_676 . . . ? Cu2 I1 Cu2 I1 0.0 2_676 . . 2_676 ? N1 C1 N2 C3 1.05(12) . . . . ? Cu2 C1 N2 C3 -168.86(9) . . . . ? N1 C1 N2 C14 -167.94(9) . . . . ? Cu2 C1 N2 C14 22.15(14) . . . . ? C1 N1 C2 C3 1.55(15) . . . . ? C4 N1 C2 C3 -179.19(10) . . . . ? N1 C2 C3 N2 -0.83(15) . . . . ? C1 N2 C3 C2 -0.14(15) . . . . ? C14 N2 C3 C2 168.73(11) . . . . ? C1 N1 C4 C9 -32.94(14) . . . . ? C2 N1 C4 C9 147.91(12) . . . . ? C1 N1 C4 C10 88.25(13) . . . . ? C2 N1 C4 C10 -90.91(13) . . . . ? C1 N1 C4 C5 -152.02(10) . . . . ? C2 N1 C4 C5 28.83(14) . . . . ? N1 C4 C5 C6 -179.78(9) . . . . ? C9 C4 C5 C6 59.98(12) . . . . ? C10 C4 C5 C6 -59.72(12) . . . . ? C4 C5 C6 C7 -60.24(13) . . . . ? C4 C5 C6 C12 59.85(13) . . . . ? C12 C6 C7 C8 -60.52(13) . . . . ? C5 C6 C7 C8 59.14(14) . . . . ? C6 C7 C8 C13 60.47(14) . . . . ? C6 C7 C8 C9 -59.32(15) . . . . ? N1 C4 C9 C8 -179.83(11) . . . . ? C10 C4 C9 C8 59.12(14) . . . . ? C5 C4 C9 C8 -60.11(14) . . . . ? C13 C8 C9 C4 -59.86(16) . . . . ? C7 C8 C9 C4 60.51(15) . . . . ? N1 C4 C10 C11 179.86(10) . . . . ? C9 C4 C10 C11 -58.76(13) . . . . ? C5 C4 C10 C11 59.97(13) . . . . ? C4 C10 C11 C13 59.74(13) . . . . ? C4 C10 C11 C12 -60.76(13) . . . . ? C13 C11 C12 C6 -58.93(13) . . . . ? C10 C11 C12 C6 61.18(13) . . . . ? C7 C6 C12 C11 59.85(12) . . . . ? C5 C6 C12 C11 -60.48(14) . . . . ? C12 C11 C13 C8 58.72(13) . . . . ? C10 C11 C13 C8 -61.23(13) . . . . ? C7 C8 C13 C11 -59.54(13) . . . . ? C9 C8 C13 C11 60.95(15) . . . . ? C1 N2 C14 C20 65.00(12) . . . . ? C3 N2 C14 C20 -102.47(13) . . . . ? C1 N2 C14 C15 -175.98(10) . . . . ? C3 N2 C14 C15 16.55(14) . . . . ? C1 N2 C14 C19 -55.43(13) . . . . ? C3 N2 C14 C19 137.10(11) . . . . ? N2 C14 C15 C16 -178.39(9) . . . . ? C20 C14 C15 C16 -60.00(12) . . . . ? C19 C14 C15 C16 59.74(12) . . . . ? C14 C15 C16 C17 -59.92(13) . . . . ? C14 C15 C16 C22 60.19(13) . . . . ? C22 C16 C17 C18 -60.43(12) . . . . ? C15 C16 C17 C18 59.87(13) . . . . ? C16 C17 C18 C23 59.88(13) . . . . ? C16 C17 C18 C19 -60.30(12) . . . . ? N2 C14 C19 C18 177.88(9) . . . . ? C20 C14 C19 C18 58.54(11) . . . . ? C15 C14 C19 C18 -60.71(12) . . . . ? C17 C18 C19 C14 61.19(12) . . . . ? C23 C18 C19 C14 -59.43(13) . . . . ? N2 C14 C20 C21 179.72(10) . . . . ? C15 C14 C20 C21 59.95(13) . . . . ? C19 C14 C20 C21 -59.13(12) . . . . ? C14 C20 C21 C23 60.09(13) . . . . ? C14 C20 C21 C22 -59.83(12) . . . . ? C23 C21 C22 C16 -60.23(13) . . . . ? C20 C21 C22 C16 59.31(13) . . . . ? C17 C16 C22 C21 60.93(13) . . . . ? C15 C16 C22 C21 -59.61(14) . . . . ? C22 C21 C23 C18 59.13(12) . . . . ? C20 C21 C23 C18 -60.81(12) . . . . ? C17 C18 C23 C21 -59.18(12) . . . . ? C19 C18 C23 C21 60.80(12) . . . . ? _diffrn_measured_fraction_theta_max 0.849 _diffrn_reflns_theta_full 39.91 _diffrn_measured_fraction_theta_full 0.849 _refine_diff_density_max 1.735 _refine_diff_density_min -2.048 _refine_diff_density_rms 0.100 # Attachment '- 4a-CCDC750320.txt' data_nol137 _database_code_depnum_ccdc_archive 'CCDC 750320' #TrackingRef '- 4a-CCDC750320.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Cl Cu N2' _chemical_formula_weight 403.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 14.694(3) _cell_length_b 28.998(5) _cell_length_c 9.4788(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4038.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6080 _cell_measurement_theta_min 2.652 _cell_measurement_theta_max 26.463 _exptl_crystal_description needle _exptl_crystal_colour light _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 1.219 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.747915 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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 9457 _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1784 _reflns_number_gt 1502 _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 '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^)+(0.1144P)^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 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 -0.02(3) _refine_ls_number_reflns 1784 _refine_ls_number_parameters 130 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.008 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 0.2500 0.2500 -0.45232(8) 0.0421(3) Uani 1 2 d SU . . Cl1 Cl 0.2500 0.2500 -0.6729(2) 0.0474(6) Uani 1 2 d SU . . N1 N 0.1932(3) 0.27298(14) -0.1660(5) 0.0403(10) Uani 1 1 d U . . C1 C 0.1183(3) 0.30018(17) -0.2192(6) 0.0414(10) Uani 1 1 d U . . C2 C 0.0353(4) 0.27869(18) -0.2433(6) 0.0447(12) Uani 1 1 d U . . C3 C -0.0352(4) 0.30542(19) -0.3029(6) 0.0476(12) Uani 1 1 d U . . H3 H -0.095(3) 0.2898(15) -0.334(5) 0.021(10) Uiso 1 1 d . . . C4 C -0.0196(4) 0.3520(2) -0.3403(7) 0.0475(13) Uani 1 1 d U . . C5 C 0.0620(4) 0.3720(2) -0.3096(7) 0.0485(12) Uani 1 1 d U . . H5 H 0.075(5) 0.409(3) -0.358(8) 0.08(2) Uiso 1 1 d . . . C6 C 0.1329(4) 0.34693(18) -0.2482(6) 0.0463(12) Uani 1 1 d U . . C7 C 0.0182(4) 0.2288(2) -0.2107(10) 0.0611(18) Uani 1 1 d U . . H7A H 0.0721 0.2106 -0.2355 0.092 Uiso 1 1 calc R . . H7B H -0.0341 0.2179 -0.2655 0.092 Uiso 1 1 calc R . . H7C H 0.0054 0.2253 -0.1098 0.092 Uiso 1 1 calc R . . C8 C -0.0947(4) 0.3787(2) -0.4108(8) 0.0620(17) Uani 1 1 d U . . H8A H -0.0797 0.3833 -0.5105 0.093 Uiso 1 1 calc R . . H8B H -0.1015 0.4088 -0.3645 0.093 Uiso 1 1 calc R . . H8C H -0.1519 0.3615 -0.4031 0.093 Uiso 1 1 calc R . . C9 C 0.2236(4) 0.3698(2) -0.2159(8) 0.0514(13) Uani 1 1 d U . . H9A H 0.2219 0.4020 -0.2469 0.077 Uiso 1 1 calc R . . H9B H 0.2723 0.3535 -0.2658 0.077 Uiso 1 1 calc R . . H9C H 0.2350 0.3686 -0.1141 0.077 Uiso 1 1 calc R . . C10 C 0.2500 0.2500 -0.2460(10) 0.0309(17) Uani 1 2 d SU . . C11 C 0.2126(4) 0.2649(2) -0.0302(7) 0.0463(12) Uani 1 1 d U . . H11 H 0.183(3) 0.2741(12) 0.048(5) 0.008(9) 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 0.0403(5) 0.0416(5) 0.0444(5) 0.000 0.000 0.0022(4) Cl1 0.0477(13) 0.0492(14) 0.0453(13) 0.000 0.000 -0.0015(8) N1 0.038(2) 0.032(2) 0.051(2) -0.0032(17) -0.0014(18) 0.0067(17) C1 0.035(2) 0.040(2) 0.049(3) 0.001(2) 0.002(2) 0.0017(18) C2 0.042(3) 0.035(3) 0.056(3) -0.005(2) 0.000(2) 0.000(2) C3 0.041(3) 0.044(3) 0.057(3) 0.003(2) -0.005(3) 0.000(2) C4 0.042(3) 0.039(3) 0.061(4) 0.000(3) -0.007(2) 0.004(2) C5 0.046(3) 0.045(3) 0.054(3) 0.005(3) 0.000(2) 0.005(2) C6 0.041(3) 0.040(2) 0.058(3) -0.004(2) -0.002(2) 0.000(2) C7 0.068(4) 0.039(3) 0.076(4) 0.011(4) -0.015(4) -0.013(3) C8 0.044(3) 0.064(4) 0.077(4) 0.014(3) -0.013(3) 0.007(3) C9 0.045(3) 0.044(3) 0.066(4) 0.001(3) -0.006(3) -0.004(2) C10 0.025(4) 0.028(4) 0.040(3) 0.000 0.000 -0.003(2) C11 0.042(3) 0.045(3) 0.051(3) -0.003(3) 0.009(3) 0.006(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 Cu1 C10 1.956(10) . ? Cu1 Cl1 2.091(2) . ? N1 C10 1.310(8) . ? N1 C11 1.339(8) . ? N1 C1 1.445(7) . ? C1 C6 1.400(7) . ? C1 C2 1.388(7) . ? C2 C3 1.412(9) . ? C2 C7 1.501(8) . ? C3 C4 1.417(8) . ? C4 C5 1.364(8) . ? C4 C8 1.504(8) . ? C5 C6 1.398(8) . ? C6 C9 1.520(8) . ? C10 N1 1.310(8) 14 ? C11 C11 1.399(12) 14 ? 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 C10 Cu1 Cl1 180.000(1) . . ? C10 N1 C11 109.4(5) . . ? C10 N1 C1 124.1(5) . . ? C11 N1 C1 126.3(5) . . ? C6 C1 C2 122.5(5) . . ? C6 C1 N1 118.7(4) . . ? C2 C1 N1 118.8(4) . . ? C1 C2 C3 117.7(5) . . ? C1 C2 C7 123.1(5) . . ? C3 C2 C7 119.2(5) . . ? C2 C3 C4 120.3(5) . . ? C5 C4 C3 119.7(5) . . ? C5 C4 C8 121.4(6) . . ? C3 C4 C8 118.9(5) . . ? C4 C5 C6 121.5(5) . . ? C1 C6 C5 118.2(5) . . ? C1 C6 C9 121.1(5) . . ? C5 C6 C9 120.7(5) . . ? N1 C10 N1 109.3(8) . 14 ? N1 C10 Cu1 125.4(4) . . ? N1 C10 Cu1 125.4(4) 14 . ? N1 C11 C11 106.0(3) . 14 ? 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 C10 N1 C1 C6 -91.0(6) . . . . ? C11 N1 C1 C6 93.3(7) . . . . ? C10 N1 C1 C2 87.3(6) . . . . ? C11 N1 C1 C2 -88.5(7) . . . . ? C6 C1 C2 C3 1.7(9) . . . . ? N1 C1 C2 C3 -176.4(5) . . . . ? C6 C1 C2 C7 -179.0(6) . . . . ? N1 C1 C2 C7 2.8(8) . . . . ? C1 C2 C3 C4 2.0(9) . . . . ? C7 C2 C3 C4 -177.2(6) . . . . ? C2 C3 C4 C5 -4.6(9) . . . . ? C2 C3 C4 C8 176.7(6) . . . . ? C3 C4 C5 C6 3.3(10) . . . . ? C8 C4 C5 C6 -178.0(6) . . . . ? C2 C1 C6 C5 -3.0(9) . . . . ? N1 C1 C6 C5 175.2(5) . . . . ? C2 C1 C6 C9 177.9(6) . . . . ? N1 C1 C6 C9 -3.9(8) . . . . ? C4 C5 C6 C1 0.4(9) . . . . ? C4 C5 C6 C9 179.5(6) . . . . ? C11 N1 C10 N1 -0.2(3) . . . 14 ? C1 N1 C10 N1 -176.6(5) . . . 14 ? C11 N1 C10 Cu1 179.8(3) . . . . ? C1 N1 C10 Cu1 3.4(5) . . . . ? Cl1 Cu1 C10 N1 134(100) . . . . ? Cl1 Cu1 C10 N1 -46(100) . . . 14 ? C10 N1 C11 C11 0.6(8) . . . 14 ? C1 N1 C11 C11 176.8(6) . . . 14 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.429 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.082 # Attachment '- 5b-CCDC750321.txt' data_tarrag21 _database_code_depnum_ccdc_archive 'CCDC 750321' #TrackingRef '- 5b-CCDC750321.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H26 Br Cu N2' _chemical_formula_sum 'C21 H26 Br Cu N2' _chemical_formula_weight 449.89 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.348(2) _cell_length_b 21.934(6) _cell_length_c 11.275(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.127(9) _cell_angle_gamma 90.00 _cell_volume 2064.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4943 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 24.84 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.060 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.030 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 2.999 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8699 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11952 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3739 _reflns_number_gt 2596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0773P)^2^+18.0131P] 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 3739 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.011 _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 0.27453(13) 0.32737(6) 1.03105(9) 0.0519(4) Uani 1 1 d . . . Cu1 Cu 0.03733(11) 0.30468(4) 0.96036(8) 0.0198(3) Uani 1 1 d . . . C1 C -0.1659(9) 0.2877(3) 0.8952(6) 0.0185(16) Uani 1 1 d . . . N2 N -0.2487(7) 0.2369(3) 0.9096(5) 0.0183(13) Uani 1 1 d . . . C3 C -0.4015(10) 0.2365(3) 0.8428(7) 0.0235(17) Uani 1 1 d . . . H3A H -0.4935 0.2288 0.8959 0.028 Uiso 1 1 calc R . . H3B H -0.4004 0.2053 0.7793 0.028 Uiso 1 1 calc R . . C4 C -0.4077(9) 0.3001(4) 0.7916(7) 0.0234(17) Uani 1 1 d . . . H4A H -0.4232 0.2991 0.7046 0.028 Uiso 1 1 calc R . . H4B H -0.4949 0.3243 0.8279 0.028 Uiso 1 1 calc R . . N5 N -0.2488(7) 0.3251(3) 0.8232(5) 0.0177(13) Uani 1 1 d . . . C6 C -0.2090(9) 0.1878(3) 0.9888(7) 0.0206(16) Uani 1 1 d . . . C7 C -0.2651(9) 0.1901(4) 1.1047(6) 0.0213(17) Uani 1 1 d . . . C8 C -0.2416(9) 0.1397(4) 1.1770(7) 0.0238(18) Uani 1 1 d . . . H8A H -0.2831 0.1404 1.2553 0.029 Uiso 1 1 calc R . . C9 C -0.1604(10) 0.0888(4) 1.1393(7) 0.0261(18) Uani 1 1 d . . . C10 C -0.1003(11) 0.0889(4) 1.0250(7) 0.0297(19) Uani 1 1 d . . . H10A H -0.0404 0.0547 0.9986 0.036 Uiso 1 1 calc R . . C11 C -0.1245(10) 0.1377(3) 0.9467(7) 0.0244(18) Uani 1 1 d . . . C12 C -0.3420(10) 0.2468(4) 1.1524(7) 0.031(2) Uani 1 1 d . . . H12A H -0.3857 0.2385 1.2314 0.046 Uiso 1 1 calc R . . H12B H -0.4287 0.2595 1.0992 0.046 Uiso 1 1 calc R . . H12C H -0.2619 0.2793 1.1578 0.046 Uiso 1 1 calc R . . C13 C -0.1325(13) 0.0351(4) 1.2217(8) 0.042(2) Uani 1 1 d . . . H13A H -0.1760 0.0445 1.3003 0.063 Uiso 1 1 calc R . . H13B H -0.0173 0.0272 1.2284 0.063 Uiso 1 1 calc R . . H13C H -0.1862 -0.0011 1.1897 0.063 Uiso 1 1 calc R . . C14 C -0.0535(11) 0.1347(4) 0.8237(7) 0.034(2) Uani 1 1 d . . . H14A H -0.1052 0.1652 0.7730 0.051 Uiso 1 1 calc R . . H14B H -0.0709 0.0940 0.7903 0.051 Uiso 1 1 calc R . . H14C H 0.0617 0.1430 0.8281 0.051 Uiso 1 1 calc R . . C15 C -0.2036(9) 0.3863(3) 0.7961(6) 0.0203(17) Uani 1 1 d . . . C16 C -0.1631(9) 0.4017(3) 0.6795(6) 0.0194(16) Uani 1 1 d . . . C17 C -0.1164(10) 0.4612(4) 0.6564(7) 0.0268(19) Uani 1 1 d . . . H17A H -0.0882 0.4721 0.5777 0.032 Uiso 1 1 calc R . . C18 C -0.1096(10) 0.5052(4) 0.7446(8) 0.0295(19) Uani 1 1 d . . . C19 C -0.1537(10) 0.4890(4) 0.8583(7) 0.0290(19) Uani 1 1 d . . . H19A H -0.1494 0.5188 0.9193 0.035 Uiso 1 1 calc R . . C20 C -0.2043(10) 0.4301(4) 0.8862(6) 0.0245(18) Uani 1 1 d . . . C21 C -0.1705(11) 0.3554(4) 0.5802(7) 0.0291(19) Uani 1 1 d . . . H21A H -0.2793 0.3541 0.5476 0.044 Uiso 1 1 calc R . . H21B H -0.1417 0.3151 0.6111 0.044 Uiso 1 1 calc R . . H21C H -0.0951 0.3670 0.5176 0.044 Uiso 1 1 calc R . . C22 C -0.0469(11) 0.5683(4) 0.7162(8) 0.037(2) Uani 1 1 d . . . H22A H -0.0819 0.5970 0.7776 0.055 Uiso 1 1 calc R . . H22B H -0.0888 0.5815 0.6390 0.055 Uiso 1 1 calc R . . H22C H 0.0704 0.5674 0.7136 0.055 Uiso 1 1 calc R . . C23 C -0.2608(12) 0.4157(4) 1.0105(7) 0.035(2) Uani 1 1 d . . . H23A H -0.1804 0.3905 1.0508 0.052 Uiso 1 1 calc R . . H23B H -0.3625 0.3934 1.0065 0.052 Uiso 1 1 calc R . . H23C H -0.2761 0.4537 1.0546 0.052 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 0.0413(6) 0.0728(8) 0.0415(6) -0.0040(5) -0.0069(5) -0.0001(5) Cu1 0.0207(5) 0.0225(5) 0.0162(5) 0.0011(4) -0.0029(3) -0.0008(4) C1 0.024(4) 0.021(4) 0.011(3) 0.001(3) 0.000(3) 0.009(3) N2 0.025(3) 0.014(3) 0.015(3) 0.003(2) -0.002(3) 0.001(3) C3 0.027(4) 0.022(4) 0.022(4) 0.001(3) -0.007(3) -0.003(3) C4 0.023(4) 0.024(4) 0.023(4) 0.002(3) -0.001(3) 0.002(3) N5 0.025(3) 0.013(3) 0.015(3) 0.002(2) 0.000(3) -0.001(3) C6 0.020(4) 0.021(4) 0.021(4) 0.004(3) -0.003(3) -0.005(3) C7 0.017(4) 0.027(4) 0.020(4) 0.006(3) -0.007(3) -0.002(3) C8 0.021(4) 0.034(5) 0.017(4) 0.003(3) -0.004(3) -0.013(4) C9 0.033(5) 0.018(4) 0.028(4) 0.010(3) -0.007(4) -0.006(4) C10 0.042(5) 0.016(4) 0.032(5) 0.003(3) 0.003(4) 0.004(4) C11 0.030(4) 0.015(4) 0.028(4) 0.002(3) -0.003(4) -0.003(3) C12 0.034(5) 0.035(5) 0.024(4) -0.002(4) 0.005(4) 0.007(4) C13 0.063(7) 0.025(5) 0.038(5) 0.012(4) -0.001(5) 0.001(5) C14 0.051(6) 0.028(5) 0.022(4) 0.006(4) 0.009(4) 0.006(4) C15 0.024(4) 0.021(4) 0.016(4) 0.003(3) 0.002(3) -0.001(3) C16 0.020(4) 0.019(4) 0.019(4) 0.002(3) 0.000(3) 0.006(3) C17 0.029(5) 0.027(5) 0.024(4) 0.013(4) 0.000(3) 0.000(4) C18 0.030(5) 0.019(4) 0.039(5) 0.008(4) -0.001(4) 0.000(4) C19 0.034(5) 0.019(4) 0.034(5) -0.004(4) -0.009(4) -0.002(4) C20 0.035(5) 0.023(4) 0.016(4) 0.001(3) -0.005(3) 0.003(4) C21 0.038(5) 0.027(5) 0.023(4) 0.000(4) 0.003(4) -0.001(4) C22 0.046(6) 0.017(4) 0.048(6) 0.007(4) 0.000(4) 0.003(4) C23 0.057(6) 0.026(5) 0.021(4) -0.008(4) 0.008(4) 0.000(4) _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 2.1903(14) . ? Cu1 C1 1.884(7) . ? C1 N2 1.323(10) . ? C1 N5 1.345(9) . ? N2 C6 1.437(9) . ? N2 C3 1.480(9) . ? C3 C4 1.510(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N5 1.479(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N5 C15 1.428(10) . ? C6 C11 1.389(11) . ? C6 C7 1.390(11) . ? C7 C8 1.388(11) . ? C7 C12 1.499(11) . ? C8 C9 1.373(12) . ? C8 H8A 0.9500 . ? C9 C10 1.385(11) . ? C9 C13 1.518(11) . ? C10 C11 1.400(11) . ? C10 H10A 0.9500 . ? C11 C14 1.511(11) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.398(11) . ? C15 C16 1.399(10) . ? C16 C17 1.386(11) . ? C16 C21 1.514(11) . ? C17 C18 1.387(12) . ? C17 H17A 0.9500 . ? C18 C19 1.380(12) . ? C18 C22 1.516(12) . ? C19 C20 1.395(11) . ? C19 H19A 0.9500 . ? C20 C23 1.513(11) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 Br1 177.7(2) . . ? N2 C1 N5 108.7(6) . . ? N2 C1 Cu1 126.1(5) . . ? N5 C1 Cu1 125.2(6) . . ? C1 N2 C6 126.0(6) . . ? C1 N2 C3 113.1(6) . . ? C6 N2 C3 120.6(6) . . ? N2 C3 C4 102.6(6) . . ? N2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? N2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.2 . . ? N5 C4 C3 102.8(6) . . ? N5 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N5 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? C1 N5 C15 124.5(6) . . ? C1 N5 C4 112.3(6) . . ? C15 N5 C4 122.3(6) . . ? C11 C6 C7 121.5(7) . . ? C11 C6 N2 119.8(7) . . ? C7 C6 N2 118.6(7) . . ? C8 C7 C6 118.3(7) . . ? C8 C7 C12 120.7(7) . . ? C6 C7 C12 120.9(7) . . ? C9 C8 C7 122.4(7) . . ? C9 C8 H8A 118.8 . . ? C7 C8 H8A 118.8 . . ? C8 C9 C10 117.8(7) . . ? C8 C9 C13 121.1(8) . . ? C10 C9 C13 121.0(8) . . ? C9 C10 C11 122.4(8) . . ? C9 C10 H10A 118.8 . . ? C11 C10 H10A 118.8 . . ? C6 C11 C10 117.5(7) . . ? C6 C11 C14 123.2(7) . . ? C10 C11 C14 119.3(7) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 121.2(7) . . ? C20 C15 N5 119.2(6) . . ? C16 C15 N5 119.6(6) . . ? C17 C16 C15 118.2(7) . . ? C17 C16 C21 120.2(7) . . ? C15 C16 C21 121.5(7) . . ? C16 C17 C18 122.1(7) . . ? C16 C17 H17A 119.0 . . ? C18 C17 H17A 119.0 . . ? C19 C18 C17 118.4(7) . . ? C19 C18 C22 121.6(8) . . ? C17 C18 C22 119.9(8) . . ? C18 C19 C20 121.9(7) . . ? C18 C19 H19A 119.0 . . ? C20 C19 H19A 119.0 . . ? C19 C20 C15 118.1(7) . . ? C19 C20 C23 119.9(7) . . ? C15 C20 C23 122.1(7) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 N2 C6 -173.7(6) . . . . ? Cu1 C1 N2 C6 8.1(10) . . . . ? N5 C1 N2 C3 0.7(8) . . . . ? Cu1 C1 N2 C3 -177.5(5) . . . . ? C1 N2 C3 C4 -5.2(8) . . . . ? C6 N2 C3 C4 169.5(6) . . . . ? N2 C3 C4 N5 7.0(7) . . . . ? N2 C1 N5 C15 174.1(6) . . . . ? Cu1 C1 N5 C15 -7.6(10) . . . . ? N2 C1 N5 C4 4.5(8) . . . . ? Cu1 C1 N5 C4 -177.3(5) . . . . ? C3 C4 N5 C1 -7.5(8) . . . . ? C3 C4 N5 C15 -177.4(6) . . . . ? C1 N2 C6 C11 -95.5(9) . . . . ? C3 N2 C6 C11 90.5(9) . . . . ? C1 N2 C6 C7 88.3(9) . . . . ? C3 N2 C6 C7 -85.7(9) . . . . ? C11 C6 C7 C8 -3.0(11) . . . . ? N2 C6 C7 C8 173.1(6) . . . . ? C11 C6 C7 C12 174.0(7) . . . . ? N2 C6 C7 C12 -9.9(11) . . . . ? C6 C7 C8 C9 2.3(11) . . . . ? C12 C7 C8 C9 -174.7(7) . . . . ? C7 C8 C9 C10 0.3(12) . . . . ? C7 C8 C9 C13 178.3(8) . . . . ? C8 C9 C10 C11 -2.3(13) . . . . ? C13 C9 C10 C11 179.7(8) . . . . ? C7 C6 C11 C10 1.1(11) . . . . ? N2 C6 C11 C10 -174.9(7) . . . . ? C7 C6 C11 C14 -176.5(8) . . . . ? N2 C6 C11 C14 7.5(12) . . . . ? C9 C10 C11 C6 1.6(12) . . . . ? C9 C10 C11 C14 179.3(8) . . . . ? C1 N5 C15 C20 -65.8(10) . . . . ? C4 N5 C15 C20 102.8(8) . . . . ? C1 N5 C15 C16 115.6(8) . . . . ? C4 N5 C15 C16 -75.7(9) . . . . ? C20 C15 C16 C17 2.9(11) . . . . ? N5 C15 C16 C17 -178.6(7) . . . . ? C20 C15 C16 C21 -176.7(7) . . . . ? N5 C15 C16 C21 1.8(11) . . . . ? C15 C16 C17 C18 -0.3(12) . . . . ? C21 C16 C17 C18 179.3(7) . . . . ? C16 C17 C18 C19 -1.1(12) . . . . ? C16 C17 C18 C22 175.8(8) . . . . ? C17 C18 C19 C20 0.0(13) . . . . ? C22 C18 C19 C20 -176.9(8) . . . . ? C18 C19 C20 C15 2.5(12) . . . . ? C18 C19 C20 C23 -176.3(8) . . . . ? C16 C15 C20 C19 -3.9(12) . . . . ? N5 C15 C20 C19 177.6(7) . . . . ? C16 C15 C20 C23 174.8(8) . . . . ? N5 C15 C20 C23 -3.7(12) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.934 _refine_diff_density_min -1.359 _refine_diff_density_rms 0.147 # Attachment '- 6b-CCDC750322.txt' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 750322' #TrackingRef '- 6b-CCDC750322.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 Br Cu N2' _chemical_formula_weight 375.81 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 12.051(5) _cell_length_b 23.197(10) _cell_length_c 12.516(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.761(12) _cell_angle_gamma 90.00 _cell_volume 3495(3) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 3.527 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6198 _exptl_absorpt_correction_T_max 0.9328 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21766 _diffrn_reflns_av_R_equivalents 0.1360 _diffrn_reflns_av_sigmaI/netI 0.1422 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.32 _reflns_number_total 6339 _reflns_number_gt 3524 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.2000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6339 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3046 _refine_ls_R_factor_gt 0.2399 _refine_ls_wR_factor_ref 0.5766 _refine_ls_wR_factor_gt 0.5451 _refine_ls_goodness_of_fit_ref 1.851 _refine_ls_restrained_S_all 1.851 _refine_ls_shift/su_max 0.088 _refine_ls_shift/su_mean 0.023 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.9892(3) 0.09788(12) 0.8732(2) 0.0560(9) Uiso 1 1 d . . . Br2 Br 0.6660(3) 0.10338(14) 0.9468(3) 0.0678(10) Uiso 1 1 d . . . Br3 Br 0.9122(3) 0.06727(13) 1.1636(2) 0.0591(9) Uiso 1 1 d . . . Cu1 Cu 1.0581(3) 0.04844(14) 1.0348(3) 0.0548(11) Uiso 1 1 d . . . Cu2 Cu 0.7747(5) 0.1443(3) 1.0750(5) 0.112(2) Uiso 1 1 d . . . Cu3 Cu 0.8420(3) 0.04559(15) 0.9690(3) 0.0613(11) Uiso 1 1 d . . . N1 N 0.881(2) 0.2498(11) 1.125(2) 0.065(7) Uiso 1 1 d . . . N2 N 0.728(2) 0.2411(11) 1.214(2) 0.066(7) Uiso 1 1 d . . . N3 N 1.3010(18) 0.0593(8) 1.0155(16) 0.041(5) Uiso 1 1 d . . . N4 N 1.2599(19) 0.0422(9) 1.1758(18) 0.048(5) Uiso 1 1 d . . . C1 C 0.795(3) 0.2164(14) 1.140(3) 0.071(9) Uiso 1 1 d . . . C2 C 0.782(3) 0.2976(14) 1.241(3) 0.072(9) Uiso 1 1 d . . . C3 C 0.873(4) 0.3030(19) 1.194(4) 0.101(13) Uiso 1 1 d . . . C4 C 0.983(3) 0.2330(12) 1.070(2) 0.058(7) Uiso 1 1 d . . . C5 C 1.071(3) 0.2222(15) 1.157(3) 0.079(10) Uiso 1 1 d . . . C6 C 1.181(3) 0.1945(16) 1.105(3) 0.084(10) Uiso 1 1 d . . . C7 C 1.220(4) 0.2449(19) 1.029(4) 0.106(13) Uiso 1 1 d . . . C8 C 1.112(4) 0.2668(17) 0.943(3) 0.093(11) Uiso 1 1 d . . . C9 C 1.022(3) 0.2799(17) 1.000(3) 0.089(11) Uiso 1 1 d . . . C10 C 0.538(3) 0.2555(14) 1.264(3) 0.071(9) Uiso 1 1 d . . . C11 C 0.438(3) 0.2217(13) 1.321(2) 0.058(7) Uiso 1 1 d . . . C12 C 0.462(3) 0.1969(15) 1.430(3) 0.079(10) Uiso 1 1 d . . . C13 C 0.579(3) 0.1587(15) 1.431(3) 0.075(9) Uiso 1 1 d . . . C14 C 0.668(4) 0.1880(19) 1.384(4) 0.108(13) Uiso 1 1 d . . . C15 C 0.641(3) 0.2104(17) 1.257(3) 0.088(11) Uiso 1 1 d . . . C17 C 1.216(3) 0.0388(13) 1.078(2) 0.061(8) Uiso 1 1 d . . . C18 C 1.387(2) 0.0759(11) 1.080(2) 0.047(6) Uiso 1 1 d . . . C19 C 1.369(3) 0.0637(15) 1.185(3) 0.074(9) Uiso 1 1 d . . . C20 C 1.196(3) 0.0275(13) 1.273(3) 0.065(8) Uiso 1 1 d . . . C21 C 1.191(3) 0.0779(18) 1.344(3) 0.091(11) Uiso 1 1 d . . . C22 C 1.120(3) 0.0575(16) 1.443(3) 0.084(11) Uiso 1 1 d . . . C23 C 1.179(3) -0.0011(18) 1.505(3) 0.095(12) Uiso 1 1 d . . . C24 C 1.187(4) -0.0412(17) 1.438(3) 0.092(12) Uiso 1 1 d . . . C25 C 1.256(3) -0.0268(17) 1.322(3) 0.090(11) Uiso 1 1 d . . . C26 C 1.298(2) 0.0598(10) 0.8970(18) 0.037(5) Uiso 1 1 d . . . C27 C 1.313(2) 0.1184(11) 0.855(2) 0.049(7) Uiso 1 1 d . . . C28 C 1.306(3) 0.1207(12) 0.728(2) 0.057(7) Uiso 1 1 d . . . C29 C 1.398(3) 0.0816(14) 0.686(3) 0.067(8) Uiso 1 1 d . . . C30 C 1.382(3) 0.0178(14) 0.727(3) 0.070(9) Uiso 1 1 d . . . C31 C 1.391(2) 0.0160(10) 0.8513(18) 0.037(5) Uiso 1 1 d . . . _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 2.436(5) . ? Br1 Cu3 2.502(5) . ? Br2 Cu2 2.234(7) . ? Br2 Cu3 2.514(5) . ? Br3 Cu1 2.481(5) . ? Br3 Cu3 2.589(5) . ? Br3 Cu2 2.645(7) . ? Cu1 C17 1.96(3) . ? Cu1 Cu3 2.493(5) 3_757 ? Cu1 Cu3 2.694(6) . ? Cu1 Cu1 2.767(7) 3_757 ? Cu2 C1 1.87(3) . ? Cu2 Cu3 2.787(7) . ? Cu3 C17 2.15(3) 3_757 ? Cu3 Cu1 2.493(5) 3_757 ? N1 C1 1.32(4) . ? N1 C4 1.48(4) . ? N1 C3 1.51(5) . ? N2 C1 1.38(4) . ? N2 C15 1.40(4) . ? N2 C2 1.49(4) . ? N3 C18 1.34(3) . ? N3 C17 1.41(4) . ? N3 C26 1.48(3) . ? N4 C17 1.31(4) . ? N4 C19 1.41(4) . ? N4 C20 1.51(4) . ? C2 C3 1.28(5) . ? C4 C5 1.50(5) . ? C4 C9 1.49(5) . ? C5 C6 1.63(5) . ? C6 C7 1.60(6) . ? C7 C8 1.73(6) . ? C8 C9 1.36(5) . ? C10 C11 1.64(4) . ? C10 C15 1.62(5) . ? C11 C12 1.49(4) . ? C12 C13 1.67(5) . ? C13 C14 1.42(5) . ? C14 C15 1.69(6) . ? C17 Cu3 2.15(3) 3_757 ? C18 C19 1.37(4) . ? C20 C21 1.48(5) . ? C20 C25 1.56(5) . ? C21 C22 1.61(5) . ? C22 C23 1.71(6) . ? C23 C24 1.26(5) . ? C24 C25 1.74(5) . ? C26 C27 1.47(4) . ? C26 C31 1.64(3) . ? C27 C28 1.59(4) . ? C28 C29 1.54(4) . ? C29 C30 1.58(5) . ? C30 C31 1.55(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 Cu1 Br1 Cu3 66.10(15) . . ? Cu2 Br2 Cu3 71.6(2) . . ? Cu1 Br3 Cu3 64.15(15) . . ? Cu1 Br3 Cu2 107.20(19) . . ? Cu3 Br3 Cu2 64.34(17) . . ? C17 Cu1 Br1 124.8(9) . . ? C17 Cu1 Br3 123.1(9) . . ? Br1 Cu1 Br3 103.47(17) . . ? C17 Cu1 Cu3 56.2(9) . 3_757 ? Br1 Cu1 Cu3 122.78(18) . 3_757 ? Br3 Cu1 Cu3 121.63(18) . 3_757 ? C17 Cu1 Cu3 171.9(9) . . ? Br1 Cu1 Cu3 58.13(13) . . ? Br3 Cu1 Cu3 59.87(14) . . ? Cu3 Cu1 Cu3 115.66(16) 3_757 . ? C17 Cu1 Cu1 117.6(9) . 3_757 ? Br1 Cu1 Cu1 88.49(19) . 3_757 ? Br3 Cu1 Cu1 89.07(19) . 3_757 ? Cu3 Cu1 Cu1 61.36(16) 3_757 3_757 ? Cu3 Cu1 Cu1 54.30(15) . 3_757 ? C1 Cu2 Br2 138.8(11) . . ? C1 Cu2 Br3 110.8(11) . . ? Br2 Cu2 Br3 110.3(3) . . ? C1 Cu2 Cu3 155.1(11) . . ? Br2 Cu2 Cu3 58.86(18) . . ? Br3 Cu2 Cu3 56.85(16) . . ? C17 Cu3 Cu1 49.3(9) 3_757 3_757 ? C17 Cu3 Br1 122.4(8) 3_757 . ? Cu1 Cu3 Br1 93.49(17) 3_757 . ? C17 Cu3 Br2 101.3(9) 3_757 . ? Cu1 Cu3 Br2 150.5(2) 3_757 . ? Br1 Cu3 Br2 107.61(17) . . ? C17 Cu3 Br3 121.5(8) 3_757 . ? Cu1 Cu3 Br3 92.98(17) 3_757 . ? Br1 Cu3 Br3 98.62(17) . . ? Br2 Cu3 Br3 103.67(17) . . ? C17 Cu3 Cu1 113.7(9) 3_757 . ? Cu1 Cu3 Cu1 64.34(16) 3_757 . ? Br1 Cu3 Cu1 55.77(13) . . ? Br2 Cu3 Cu1 144.99(18) . . ? Br3 Cu3 Cu1 55.98(13) . . ? C17 Cu3 Cu2 141.4(9) 3_757 . ? Cu1 Cu3 Cu2 151.7(2) 3_757 . ? Br1 Cu3 Cu2 93.38(18) . . ? Br2 Cu3 Cu2 49.53(17) . . ? Br3 Cu3 Cu2 58.81(17) . . ? Cu1 Cu3 Cu2 97.7(2) . . ? C1 N1 C4 126(3) . . ? C1 N1 C3 109(3) . . ? C4 N1 C3 124(3) . . ? C1 N2 C15 121(3) . . ? C1 N2 C2 105(3) . . ? C15 N2 C2 133(3) . . ? C18 N3 C17 109(2) . . ? C18 N3 C26 125(2) . . ? C17 N3 C26 125(2) . . ? C17 N4 C19 116(2) . . ? C17 N4 C20 122(3) . . ? C19 N4 C20 122(3) . . ? N1 C1 N2 110(3) . . ? N1 C1 Cu2 124(2) . . ? N2 C1 Cu2 126(2) . . ? C3 C2 N2 111(3) . . ? C2 C3 N1 105(3) . . ? N1 C4 C5 106(2) . . ? N1 C4 C9 112(3) . . ? C5 C4 C9 108(3) . . ? C4 C5 C6 110(3) . . ? C5 C6 C7 103(3) . . ? C6 C7 C8 111(3) . . ? C9 C8 C7 109(3) . . ? C8 C9 C4 116(3) . . ? C11 C10 C15 107(3) . . ? C12 C11 C10 118(3) . . ? C11 C12 C13 109(3) . . ? C14 C13 C12 113(3) . . ? C13 C14 C15 115(4) . . ? N2 C15 C14 114(3) . . ? N2 C15 C10 106(3) . . ? C14 C15 C10 105(3) . . ? N4 C17 N3 103(3) . . ? N4 C17 Cu1 127(2) . . ? N3 C17 Cu1 122(2) . . ? N4 C17 Cu3 115(2) . 3_757 ? N3 C17 Cu3 112.8(19) . 3_757 ? Cu1 C17 Cu3 74.5(11) . 3_757 ? N3 C18 C19 111(3) . . ? N4 C19 C18 101(3) . . ? C21 C20 N4 110(3) . . ? C21 C20 C25 116(3) . . ? N4 C20 C25 105(3) . . ? C20 C21 C22 106(3) . . ? C21 C22 C23 111(3) . . ? C24 C23 C22 109(4) . . ? C23 C24 C25 118(4) . . ? C20 C25 C24 105(3) . . ? C27 C26 N3 112(2) . . ? C27 C26 C31 110.3(19) . . ? N3 C26 C31 111.1(19) . . ? C26 C27 C28 113(2) . . ? C29 C28 C27 108(2) . . ? C28 C29 C30 110(2) . . ? C31 C30 C29 111(2) . . ? C30 C31 C26 108(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 6.381 _refine_diff_density_min -4.452 _refine_diff_density_rms 0.417 # Attachment '- 6c-CCDC750323.txt' data_tarrag20 _database_code_depnum_ccdc_archive 'CCDC 750323' #TrackingRef '- 6c-CCDC750323.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H72 Cu3 I3 N6,C2 H3 N,(C6 H14)0.25' _chemical_formula_sum 'C48.50 H78.50 Cu3 I3 N7' _chemical_formula_weight 1331.00 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 P2(1)/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 12.542(2) _cell_length_b 17.245(3) _cell_length_c 26.111(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.885(8) _cell_angle_gamma 90.00 _cell_volume 5546.0(17) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 12139 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 26.39 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.030 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.030 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2658 _exptl_absorpt_coefficient_mu 2.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9172 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32935 _diffrn_reflns_av_R_equivalents 0.0929 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 9944 _reflns_number_gt 6872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. An acetonitrile solvent molecule was located and refined. A disordered quarter weight hexane molecule was refined isotropically without 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^)+(0.0511P)^2^+30.7412P] 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 9944 _refine_ls_number_parameters 544 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.008 _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 0.72785(8) 0.26732(6) 0.21917(4) 0.0248(2) Uani 1 1 d . . . Cu2 Cu 0.87269(8) 0.17484(6) 0.25297(4) 0.0256(2) Uani 1 1 d . . . Cu3 Cu 0.76897(9) 0.05211(6) 0.26473(4) 0.0330(3) Uani 1 1 d . . . I1 I 0.62918(4) 0.17752(3) 0.27222(2) 0.02807(15) Uani 1 1 d . . . I2 I 0.83252(5) 0.07690(3) 0.17497(2) 0.02785(15) Uani 1 1 d . . . I3 I 0.96308(4) 0.09786(3) 0.33357(2) 0.02442(14) Uani 1 1 d . . . C1 C 0.6665(6) 0.3313(4) 0.1604(3) 0.0206(18) Uani 1 1 d . . . N2 N 0.6170(5) 0.3061(4) 0.1130(3) 0.0245(16) Uani 1 1 d . . . C3 C 0.5858(7) 0.3671(5) 0.0797(3) 0.026(2) Uani 1 1 d . . . H3A H 0.5497 0.3639 0.0443 0.032 Uiso 1 1 calc R . . C4 C 0.6161(7) 0.4320(5) 0.1068(3) 0.0257(19) Uani 1 1 d . . . H4A H 0.6057 0.4837 0.0943 0.031 Uiso 1 1 calc R . . N5 N 0.6650(5) 0.4098(4) 0.1560(3) 0.0245(16) Uani 1 1 d . . . C6 C 0.5959(7) 0.2235(5) 0.1014(3) 0.030(2) Uani 1 1 d . . . H6A H 0.6450 0.1929 0.1287 0.036 Uiso 1 1 calc R . . C7 C 0.4809(7) 0.2021(5) 0.1043(3) 0.032(2) Uani 1 1 d . . . H7A H 0.4301 0.2328 0.0784 0.038 Uiso 1 1 calc R . . H7B H 0.4667 0.2149 0.1394 0.038 Uiso 1 1 calc R . . C8 C 0.4608(10) 0.1158(6) 0.0936(4) 0.051(3) Uani 1 1 d . . . H8A H 0.5065 0.0852 0.1215 0.061 Uiso 1 1 calc R . . H8B H 0.3838 0.1036 0.0940 0.061 Uiso 1 1 calc R . . C9 C 0.4870(10) 0.0935(6) 0.0412(4) 0.052(3) Uani 1 1 d . . . H9A H 0.4361 0.1200 0.0131 0.063 Uiso 1 1 calc R . . H9B H 0.4774 0.0369 0.0360 0.063 Uiso 1 1 calc R . . C10 C 0.6033(9) 0.1157(6) 0.0381(4) 0.052(3) Uani 1 1 d . . . H10A H 0.6545 0.0852 0.0639 0.063 Uiso 1 1 calc R . . H10B H 0.6173 0.1034 0.0029 0.063 Uiso 1 1 calc R . . C11 C 0.6223(9) 0.2018(6) 0.0490(4) 0.045(3) Uani 1 1 d . . . H11A H 0.6991 0.2145 0.0487 0.054 Uiso 1 1 calc R . . H11B H 0.5761 0.2323 0.0212 0.054 Uiso 1 1 calc R . . C12 C 0.7008(7) 0.4621(5) 0.2003(4) 0.028(2) Uani 1 1 d . . . H12A H 0.7587 0.4350 0.2255 0.034 Uiso 1 1 calc R . . C13 C 0.7491(8) 0.5367(5) 0.1833(4) 0.037(2) Uani 1 1 d . . . H13A H 0.8121 0.5242 0.1670 0.045 Uiso 1 1 calc R . . H13B H 0.6943 0.5637 0.1571 0.045 Uiso 1 1 calc R . . C14 C 0.7849(8) 0.5894(6) 0.2299(4) 0.043(3) Uani 1 1 d . . . H14A H 0.8155 0.6378 0.2184 0.052 Uiso 1 1 calc R . . H14B H 0.8425 0.5634 0.2553 0.052 Uiso 1 1 calc R . . C15 C 0.6898(7) 0.6087(5) 0.2562(4) 0.030(2) Uani 1 1 d . . . H15A H 0.7153 0.6418 0.2870 0.035 Uiso 1 1 calc R . . H15B H 0.6346 0.6382 0.2316 0.035 Uiso 1 1 calc R . . C16 C 0.6387(7) 0.5353(5) 0.2730(4) 0.032(2) Uani 1 1 d . . . H16A H 0.6909 0.5097 0.3011 0.038 Uiso 1 1 calc R . . H16B H 0.5735 0.5492 0.2873 0.038 Uiso 1 1 calc R . . C17 C 0.6070(7) 0.4793(5) 0.2282(3) 0.029(2) Uani 1 1 d . . . H17A H 0.5458 0.5015 0.2029 0.035 Uiso 1 1 calc R . . H17B H 0.5818 0.4302 0.2415 0.035 Uiso 1 1 calc R . . C21 C 0.8976(7) 0.2877(4) 0.2514(3) 0.0229(18) Uani 1 1 d . . . N22 N 0.9544(5) 0.3257(4) 0.2189(3) 0.0238(15) Uani 1 1 d . . . C23 C 1.0014(7) 0.3921(5) 0.2412(3) 0.029(2) Uani 1 1 d . . . H23A H 1.0436 0.4279 0.2258 0.035 Uiso 1 1 calc R . . C24 C 0.9765(7) 0.3972(5) 0.2890(3) 0.030(2) Uani 1 1 d . . . H24A H 0.9984 0.4370 0.3139 0.035 Uiso 1 1 calc R . . N25 N 0.9125(5) 0.3332(4) 0.2951(3) 0.0222(15) Uani 1 1 d . . . C26 C 0.9690(7) 0.2920(5) 0.1684(3) 0.0227(18) Uani 1 1 d . . . H26A H 0.9081 0.2546 0.1573 0.027 Uiso 1 1 calc R . . C27 C 0.9614(7) 0.3532(5) 0.1259(3) 0.029(2) Uani 1 1 d . . . H27A H 0.8891 0.3782 0.1204 0.035 Uiso 1 1 calc R . . H27B H 1.0171 0.3937 0.1367 0.035 Uiso 1 1 calc R . . C28 C 0.9789(8) 0.3158(6) 0.0757(3) 0.037(2) Uani 1 1 d . . . H28A H 0.9163 0.2817 0.0623 0.044 Uiso 1 1 calc R . . H28B H 0.9815 0.3567 0.0494 0.044 Uiso 1 1 calc R . . C29 C 1.0813(8) 0.2688(6) 0.0823(3) 0.037(2) Uani 1 1 d . . . H29A H 1.1447 0.3038 0.0909 0.045 Uiso 1 1 calc R . . H29B H 1.0853 0.2425 0.0490 0.045 Uiso 1 1 calc R . . C30 C 1.0868(8) 0.2085(6) 0.1250(4) 0.039(2) Uani 1 1 d . . . H30A H 1.1577 0.1814 0.1300 0.046 Uiso 1 1 calc R . . H30B H 1.0289 0.1695 0.1146 0.046 Uiso 1 1 calc R . . C31 C 1.0732(7) 0.2462(5) 0.1758(3) 0.036(2) Uani 1 1 d . . . H31A H 1.0725 0.2058 0.2026 0.043 Uiso 1 1 calc R . . H31B H 1.1354 0.2812 0.1881 0.043 Uiso 1 1 calc R . . C32 C 0.8698(7) 0.3140(5) 0.3421(3) 0.0254(19) Uani 1 1 d . . . H32A H 0.8353 0.2617 0.3365 0.030 Uiso 1 1 calc R . . C33 C 0.9615(8) 0.3082(5) 0.3892(3) 0.034(2) Uani 1 1 d . . . H33A H 1.0173 0.2713 0.3819 0.041 Uiso 1 1 calc R . . H33B H 0.9962 0.3596 0.3968 0.041 Uiso 1 1 calc R . . C34 C 0.9151(9) 0.2805(6) 0.4353(4) 0.047(3) Uani 1 1 d . . . H34A H 0.9739 0.2779 0.4665 0.057 Uiso 1 1 calc R . . H34B H 0.8853 0.2277 0.4282 0.057 Uiso 1 1 calc R . . C35 C 0.8247(10) 0.3349(8) 0.4466(4) 0.066(4) Uani 1 1 d . . . H35A H 0.7930 0.3135 0.4756 0.079 Uiso 1 1 calc R . . H35B H 0.8556 0.3865 0.4573 0.079 Uiso 1 1 calc R . . C36 C 0.7359(9) 0.3427(7) 0.3975(4) 0.053(3) Uani 1 1 d . . . H36A H 0.7000 0.2919 0.3893 0.063 Uiso 1 1 calc R . . H36B H 0.6804 0.3801 0.4043 0.063 Uiso 1 1 calc R . . C37 C 0.7832(7) 0.3703(5) 0.3509(4) 0.035(2) Uani 1 1 d . . . H37A H 0.7252 0.3730 0.3194 0.043 Uiso 1 1 calc R . . H37B H 0.8147 0.4227 0.3578 0.043 Uiso 1 1 calc R . . C41 C 0.7073(7) -0.0384(5) 0.2913(3) 0.0250(19) Uani 1 1 d . . . N42 N 0.6868(5) -0.0474(4) 0.3405(2) 0.0208(15) Uani 1 1 d . . . C43 C 0.6342(7) -0.1159(5) 0.3452(3) 0.0249(19) Uani 1 1 d . . . H43A H 0.6107 -0.1344 0.3754 0.030 Uiso 1 1 calc R . . C44 C 0.6224(7) -0.1515(5) 0.2992(3) 0.0246(19) Uani 1 1 d . . . H44A H 0.5891 -0.2005 0.2905 0.030 Uiso 1 1 calc R . . N45 N 0.6671(5) -0.1042(4) 0.2667(2) 0.0205(15) Uani 1 1 d . . . C46 C 0.7198(6) 0.0108(5) 0.3818(3) 0.0232(18) Uani 1 1 d . . . H46A H 0.7566 0.0538 0.3662 0.028 Uiso 1 1 calc R . . C47 C 0.8016(7) -0.0222(5) 0.4268(3) 0.030(2) Uani 1 1 d . . . H47A H 0.8649 -0.0428 0.4135 0.036 Uiso 1 1 calc R . . H47B H 0.7681 -0.0656 0.4428 0.036 Uiso 1 1 calc R . . C48 C 0.8399(8) 0.0400(6) 0.4681(3) 0.037(2) Uani 1 1 d . . . H48A H 0.8891 0.0163 0.4981 0.044 Uiso 1 1 calc R . . H48B H 0.8808 0.0805 0.4532 0.044 Uiso 1 1 calc R . . C49 C 0.7432(8) 0.0765(6) 0.4866(4) 0.041(2) Uani 1 1 d . . . H49A H 0.7690 0.1187 0.5116 0.049 Uiso 1 1 calc R . . H49B H 0.7069 0.0371 0.5048 0.049 Uiso 1 1 calc R . . C50 C 0.6619(7) 0.1093(5) 0.4404(4) 0.033(2) Uani 1 1 d . . . H50A H 0.5991 0.1318 0.4531 0.039 Uiso 1 1 calc R . . H50B H 0.6969 0.1512 0.4235 0.039 Uiso 1 1 calc R . . C51 C 0.6224(7) 0.0458(5) 0.4005(4) 0.033(2) Uani 1 1 d . . . H51A H 0.5839 0.0051 0.4166 0.040 Uiso 1 1 calc R . . H51B H 0.5711 0.0680 0.3705 0.040 Uiso 1 1 calc R . . C52 C 0.6709(6) -0.1185(5) 0.2117(3) 0.0228(19) Uani 1 1 d . . . H52A H 0.7319 -0.0867 0.2031 0.027 Uiso 1 1 calc R . . C53 C 0.5685(9) -0.0920(7) 0.1761(4) 0.049(3) Uani 1 1 d . . . H53A H 0.5565 -0.0362 0.1820 0.058 Uiso 1 1 calc R . . H53B H 0.5057 -0.1212 0.1841 0.058 Uiso 1 1 calc R . . C54 C 0.5763(9) -0.1048(7) 0.1195(3) 0.050(3) Uani 1 1 d . . . H54A H 0.6342 -0.0713 0.1106 0.060 Uiso 1 1 calc R . . H54B H 0.5068 -0.0897 0.0970 0.060 Uiso 1 1 calc R . . C55 C 0.6011(9) -0.1890(7) 0.1091(4) 0.054(3) Uani 1 1 d . . . H55A H 0.5399 -0.2221 0.1147 0.065 Uiso 1 1 calc R . . H55B H 0.6093 -0.1949 0.0723 0.065 Uiso 1 1 calc R . . C56 C 0.7018(11) -0.2141(6) 0.1441(4) 0.057(3) Uani 1 1 d . . . H56A H 0.7641 -0.1846 0.1358 0.069 Uiso 1 1 calc R . . H56B H 0.7145 -0.2698 0.1381 0.069 Uiso 1 1 calc R . . C57 C 0.6951(10) -0.2015(6) 0.2016(4) 0.050(3) Uani 1 1 d . . . H57A H 0.6375 -0.2350 0.2108 0.060 Uiso 1 1 calc R . . H57B H 0.7649 -0.2165 0.2239 0.060 Uiso 1 1 calc R . . N61 N 0.3819(9) 0.1204(6) 0.4689(4) 0.070(3) Uiso 1 1 d . . . C61 C 0.2938(9) 0.1411(6) 0.4634(4) 0.044(3) Uiso 1 1 d . . . C62 C 0.1833(10) 0.1606(7) 0.4538(5) 0.066(3) Uiso 1 1 d . . . H62A H 0.1468 0.1357 0.4215 0.100 Uiso 1 1 calc R . . H62B H 0.1755 0.2170 0.4504 0.100 Uiso 1 1 calc R . . H62C H 0.1504 0.1428 0.4829 0.100 Uiso 1 1 calc R . . C63A C 0.796(3) 0.560(3) 0.5322(16) 0.038(10) Uiso 0.25 1 d P . . C63B C 0.804(4) 0.594(3) 0.5192(18) 0.046(11) Uiso 0.25 1 d P . . C64 C 0.8761(18) 0.5149(13) 0.5381(9) 0.055(6) Uiso 0.50 1 d P . . C65 C 0.9519(19) 0.5281(14) 0.4987(10) 0.065(7) Uiso 0.50 1 d P . . 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 0.0314(6) 0.0191(5) 0.0227(5) 0.0015(4) 0.0018(5) -0.0012(4) Cu2 0.0308(6) 0.0155(5) 0.0303(6) 0.0035(4) 0.0048(5) -0.0027(4) Cu3 0.0492(7) 0.0207(6) 0.0327(6) 0.0006(5) 0.0166(6) -0.0120(5) I1 0.0245(3) 0.0226(3) 0.0384(3) 0.0054(3) 0.0092(3) 0.0001(2) I2 0.0392(3) 0.0213(3) 0.0247(3) 0.0006(2) 0.0103(3) -0.0003(2) I3 0.0228(3) 0.0221(3) 0.0285(3) 0.0042(2) 0.0052(2) 0.0028(2) C1 0.020(4) 0.018(4) 0.025(5) -0.006(4) 0.007(4) -0.005(3) N2 0.029(4) 0.024(4) 0.023(4) 0.002(3) 0.011(3) 0.008(3) C3 0.031(5) 0.031(5) 0.018(4) -0.002(4) 0.007(4) 0.002(4) C4 0.029(5) 0.026(5) 0.022(5) 0.008(4) 0.005(4) 0.003(4) N5 0.024(4) 0.021(4) 0.030(4) 0.002(3) 0.005(3) 0.000(3) C6 0.039(5) 0.034(5) 0.015(4) -0.004(4) 0.002(4) 0.003(4) C7 0.040(5) 0.029(5) 0.029(5) -0.009(4) 0.017(4) -0.005(4) C8 0.075(8) 0.030(6) 0.052(7) -0.009(5) 0.024(6) -0.010(5) C9 0.089(9) 0.032(6) 0.034(6) -0.011(5) 0.008(6) -0.006(6) C10 0.061(7) 0.056(7) 0.041(6) -0.016(5) 0.010(6) 0.002(6) C11 0.050(6) 0.044(6) 0.046(6) -0.024(5) 0.019(5) 0.000(5) C12 0.027(5) 0.020(5) 0.039(5) 0.001(4) 0.008(4) -0.006(4) C13 0.034(5) 0.031(5) 0.052(6) -0.006(5) 0.022(5) -0.008(4) C14 0.037(6) 0.033(6) 0.065(7) -0.009(5) 0.020(5) -0.007(4) C15 0.023(5) 0.018(5) 0.049(6) -0.002(4) 0.010(4) -0.004(4) C16 0.039(5) 0.020(5) 0.039(5) -0.001(4) 0.011(4) 0.001(4) C17 0.034(5) 0.025(5) 0.030(5) -0.002(4) 0.010(4) -0.008(4) C21 0.027(5) 0.008(4) 0.031(5) -0.001(4) 0.000(4) 0.000(3) N22 0.023(4) 0.021(4) 0.028(4) 0.009(3) 0.007(3) -0.005(3) C23 0.036(5) 0.019(5) 0.028(5) 0.003(4) -0.002(4) -0.009(4) C24 0.032(5) 0.023(5) 0.029(5) 0.005(4) -0.004(4) -0.006(4) N25 0.027(4) 0.016(4) 0.023(4) 0.004(3) 0.004(3) 0.002(3) C26 0.027(5) 0.019(4) 0.019(4) 0.007(3) -0.006(4) -0.007(4) C27 0.032(5) 0.025(5) 0.030(5) 0.010(4) 0.008(4) -0.007(4) C28 0.038(5) 0.046(6) 0.025(5) 0.008(4) 0.005(4) 0.003(5) C29 0.043(6) 0.053(7) 0.017(5) 0.007(4) 0.006(4) -0.006(5) C30 0.044(6) 0.036(6) 0.039(6) 0.000(5) 0.014(5) 0.012(5) C31 0.039(5) 0.038(6) 0.029(5) 0.012(4) 0.002(4) 0.003(4) C32 0.028(5) 0.022(5) 0.025(5) 0.002(4) 0.002(4) 0.004(4) C33 0.044(6) 0.025(5) 0.033(5) -0.004(4) 0.003(4) -0.004(4) C34 0.055(7) 0.053(7) 0.033(6) 0.006(5) 0.011(5) 0.008(5) C35 0.086(9) 0.082(9) 0.040(7) -0.003(6) 0.036(7) 0.021(7) C36 0.049(7) 0.066(8) 0.046(7) 0.002(6) 0.016(6) 0.022(6) C37 0.034(5) 0.031(5) 0.042(6) -0.005(4) 0.010(5) 0.003(4) C41 0.030(5) 0.020(5) 0.025(5) -0.003(4) 0.005(4) 0.001(4) N42 0.029(4) 0.011(3) 0.023(4) -0.004(3) 0.005(3) -0.007(3) C43 0.033(5) 0.020(5) 0.025(5) 0.004(4) 0.012(4) 0.003(4) C44 0.034(5) 0.011(4) 0.033(5) 0.000(4) 0.018(4) 0.002(4) N45 0.031(4) 0.012(3) 0.019(4) -0.001(3) 0.006(3) -0.002(3) C46 0.027(5) 0.021(4) 0.022(4) 0.001(4) 0.006(4) 0.000(4) C47 0.041(5) 0.024(5) 0.023(5) -0.007(4) 0.005(4) -0.002(4) C48 0.040(5) 0.048(6) 0.019(5) -0.008(4) -0.002(4) -0.001(5) C49 0.050(6) 0.045(6) 0.032(5) -0.018(5) 0.018(5) -0.006(5) C50 0.033(5) 0.028(5) 0.038(5) -0.016(4) 0.010(4) -0.002(4) C51 0.030(5) 0.029(5) 0.044(6) -0.002(4) 0.016(5) -0.001(4) C52 0.021(4) 0.021(4) 0.029(5) -0.006(4) 0.010(4) -0.005(3) C53 0.059(7) 0.059(7) 0.029(6) 0.004(5) 0.013(5) 0.022(6) C54 0.058(7) 0.074(8) 0.017(5) -0.006(5) 0.002(5) 0.022(6) C55 0.070(8) 0.064(8) 0.024(5) -0.007(5) -0.001(5) -0.024(6) C56 0.111(10) 0.029(6) 0.034(6) -0.010(5) 0.018(7) 0.027(6) C57 0.076(8) 0.030(6) 0.040(6) -0.006(5) 0.000(6) 0.019(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.927(8) . ? Cu1 C21 2.165(8) . ? Cu1 Cu2 2.4528(15) . ? Cu1 I1 2.5487(11) . ? Cu2 C21 1.973(8) . ? Cu2 Cu3 2.5332(14) . ? Cu2 I3 2.5642(12) . ? Cu2 I2 2.6206(12) . ? Cu3 C41 1.928(8) . ? Cu3 I2 2.6489(12) . ? Cu3 I1 2.8141(13) . ? Cu3 I3 2.8509(13) . ? C1 N2 1.349(10) . ? C1 N5 1.359(10) . ? N2 C3 1.374(11) . ? N2 C6 1.469(11) . ? C3 C4 1.341(12) . ? C3 H3A 0.9500 . ? C4 N5 1.369(10) . ? C4 H4A 0.9500 . ? N5 C12 1.470(11) . ? C6 C7 1.504(12) . ? C6 C11 1.513(12) . ? C6 H6A 1.0000 . ? C7 C8 1.527(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.516(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.525(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.521(14) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.523(11) . ? C12 C17 1.524(12) . ? C12 H12A 1.0000 . ? C13 C14 1.517(13) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.521(12) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.521(11) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(12) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C21 N25 1.369(10) . ? C21 N22 1.373(10) . ? N22 C23 1.366(10) . ? N22 C26 1.484(10) . ? C23 C24 1.346(12) . ? C23 H23A 0.9500 . ? C24 N25 1.390(10) . ? C24 H24A 0.9500 . ? N25 C32 1.466(10) . ? C26 C31 1.508(12) . ? C26 C27 1.522(11) . ? C26 H26A 1.0000 . ? C27 C28 1.515(12) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.501(13) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.517(12) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.515(12) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C37 1.507(11) . ? C32 C33 1.520(12) . ? C32 H32A 1.0000 . ? C33 C34 1.511(13) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.542(14) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.537(15) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.528(13) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C41 N45 1.355(10) . ? C41 N42 1.365(10) . ? N42 C43 1.368(10) . ? N42 C46 1.474(10) . ? C43 C44 1.332(11) . ? C43 H43A 0.9500 . ? C44 N45 1.372(10) . ? C44 H44A 0.9500 . ? N45 C52 1.466(10) . ? C46 C47 1.517(11) . ? C46 C51 1.524(11) . ? C46 H46A 1.0000 . ? C47 C48 1.532(12) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.524(13) . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C50 1.533(13) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 C51 1.529(12) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C57 1.497(12) . ? C52 C53 1.508(13) . ? C52 H52A 1.0000 . ? C53 C54 1.513(13) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.520(15) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.478(15) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 C57 1.536(13) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? N61 C61 1.144(13) . ? C61 C62 1.402(15) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63A C63B 0.70(5) . ? C63A C64 1.26(4) . ? C63B C64 1.66(5) . ? C64 C65 1.55(3) . ? C65 C65 1.54(5) 3_766 ? 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 C21 115.6(3) . . ? C1 Cu1 Cu2 144.7(2) . . ? C21 Cu1 Cu2 50.1(2) . . ? C1 Cu1 I1 128.2(2) . . ? C21 Cu1 I1 115.5(2) . . ? Cu2 Cu1 I1 79.16(4) . . ? C21 Cu2 Cu1 57.3(2) . . ? C21 Cu2 Cu3 156.0(2) . . ? Cu1 Cu2 Cu3 102.97(5) . . ? C21 Cu2 I3 118.8(2) . . ? Cu1 Cu2 I3 144.54(5) . . ? Cu3 Cu2 I3 68.01(4) . . ? C21 Cu2 I2 128.9(2) . . ? Cu1 Cu2 I2 96.82(5) . . ? Cu3 Cu2 I2 61.83(4) . . ? I3 Cu2 I2 107.12(4) . . ? C41 Cu3 Cu2 165.9(3) . . ? C41 Cu3 I2 131.1(2) . . ? Cu2 Cu3 I2 60.71(3) . . ? C41 Cu3 I1 107.4(2) . . ? Cu2 Cu3 I1 72.97(4) . . ? I2 Cu3 I1 103.47(4) . . ? C41 Cu3 I3 110.5(3) . . ? Cu2 Cu3 I3 56.51(3) . . ? I2 Cu3 I3 98.59(4) . . ? I1 Cu3 I3 102.27(4) . . ? Cu1 I1 Cu3 93.23(4) . . ? Cu2 I2 Cu3 57.46(3) . . ? Cu2 I3 Cu3 55.48(3) . . ? N2 C1 N5 104.2(7) . . ? N2 C1 Cu1 126.3(6) . . ? N5 C1 Cu1 129.4(6) . . ? C1 N2 C3 111.2(7) . . ? C1 N2 C6 122.3(7) . . ? C3 N2 C6 126.4(7) . . ? C4 C3 N2 106.6(7) . . ? C4 C3 H3A 126.7 . . ? N2 C3 H3A 126.7 . . ? C3 C4 N5 107.1(7) . . ? C3 C4 H4A 126.4 . . ? N5 C4 H4A 126.4 . . ? C1 N5 C4 110.8(7) . . ? C1 N5 C12 123.2(7) . . ? C4 N5 C12 125.6(7) . . ? N2 C6 C7 111.4(7) . . ? N2 C6 C11 111.3(7) . . ? C7 C6 C11 111.1(7) . . ? N2 C6 H6A 107.6 . . ? C7 C6 H6A 107.6 . . ? C11 C6 H6A 107.6 . . ? C6 C7 C8 110.9(8) . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 110.8(8) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 110.9(9) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 110.7(9) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C6 C11 C10 111.0(9) . . ? C6 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C6 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N5 C12 C13 111.6(7) . . ? N5 C12 C17 110.3(7) . . ? C13 C12 C17 111.1(7) . . ? N5 C12 H12A 107.9 . . ? C13 C12 H12A 107.9 . . ? C17 C12 H12A 107.9 . . ? C14 C13 C12 110.2(8) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 110.8(8) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 110.9(7) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C15 111.8(7) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C16 C17 C12 112.3(7) . . ? C16 C17 H17A 109.1 . . ? C12 C17 H17A 109.1 . . ? C16 C17 H17B 109.1 . . ? C12 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? N25 C21 N22 103.6(6) . . ? N25 C21 Cu2 123.1(6) . . ? N22 C21 Cu2 125.9(6) . . ? N25 C21 Cu1 112.8(5) . . ? N22 C21 Cu1 115.1(6) . . ? Cu2 C21 Cu1 72.5(3) . . ? C23 N22 C21 111.7(7) . . ? C23 N22 C26 126.3(7) . . ? C21 N22 C26 121.8(6) . . ? C24 C23 N22 107.0(7) . . ? C24 C23 H23A 126.5 . . ? N22 C23 H23A 126.5 . . ? C23 C24 N25 107.2(8) . . ? C23 C24 H24A 126.4 . . ? N25 C24 H24A 126.4 . . ? C21 N25 C24 110.5(7) . . ? C21 N25 C32 123.6(7) . . ? C24 N25 C32 125.8(7) . . ? N22 C26 C31 110.0(6) . . ? N22 C26 C27 112.0(7) . . ? C31 C26 C27 112.9(7) . . ? N22 C26 H26A 107.2 . . ? C31 C26 H26A 107.2 . . ? C27 C26 H26A 107.2 . . ? C28 C27 C26 109.6(7) . . ? C28 C27 H27A 109.7 . . ? C26 C27 H27A 109.7 . . ? C28 C27 H27B 109.7 . . ? C26 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? C29 C28 C27 113.0(8) . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? C27 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C28 C29 C30 112.0(7) . . ? C28 C29 H29A 109.2 . . ? C30 C29 H29A 109.2 . . ? C28 C29 H29B 109.2 . . ? C30 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? C29 C30 C31 110.5(8) . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C26 C31 C30 110.6(7) . . ? C26 C31 H31A 109.5 . . ? C30 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? N25 C32 C37 111.7(7) . . ? N25 C32 C33 110.6(7) . . ? C37 C32 C33 112.1(7) . . ? N25 C32 H32A 107.4 . . ? C37 C32 H32A 107.4 . . ? C33 C32 H32A 107.4 . . ? C34 C33 C32 108.6(8) . . ? C34 C33 H33A 110.0 . . ? C32 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? C32 C33 H33B 110.0 . . ? H33A C33 H33B 108.3 . . ? C33 C34 C35 111.7(9) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? C36 C35 C34 109.7(9) . . ? C36 C35 H35A 109.7 . . ? C34 C35 H35A 109.7 . . ? C36 C35 H35B 109.7 . . ? C34 C35 H35B 109.7 . . ? H35A C35 H35B 108.2 . . ? C37 C36 C35 111.3(9) . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36B 109.4 . . ? C35 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C32 C37 C36 108.7(8) . . ? C32 C37 H37A 110.0 . . ? C36 C37 H37A 110.0 . . ? C32 C37 H37B 110.0 . . ? C36 C37 H37B 110.0 . . ? H37A C37 H37B 108.3 . . ? N45 C41 N42 103.4(7) . . ? N45 C41 Cu3 130.2(6) . . ? N42 C41 Cu3 126.2(6) . . ? C41 N42 C43 111.2(6) . . ? C41 N42 C46 122.2(6) . . ? C43 N42 C46 126.6(6) . . ? C44 C43 N42 107.0(7) . . ? C44 C43 H43A 126.5 . . ? N42 C43 H43A 126.5 . . ? C43 C44 N45 107.1(7) . . ? C43 C44 H44A 126.4 . . ? N45 C44 H44A 126.4 . . ? C41 N45 C44 111.3(7) . . ? C41 N45 C52 121.9(6) . . ? C44 N45 C52 126.8(7) . . ? N42 C46 C47 111.5(6) . . ? N42 C46 C51 111.9(7) . . ? C47 C46 C51 111.5(7) . . ? N42 C46 H46A 107.2 . . ? C47 C46 H46A 107.2 . . ? C51 C46 H46A 107.2 . . ? C46 C47 C48 111.0(7) . . ? C46 C47 H47A 109.4 . . ? C48 C47 H47A 109.4 . . ? C46 C47 H47B 109.4 . . ? C48 C47 H47B 109.4 . . ? H47A C47 H47B 108.0 . . ? C49 C48 C47 110.5(8) . . ? C49 C48 H48A 109.5 . . ? C47 C48 H48A 109.5 . . ? C49 C48 H48B 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 108.1 . . ? C48 C49 C50 110.8(7) . . ? C48 C49 H49A 109.5 . . ? C50 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? C50 C49 H49B 109.5 . . ? H49A C49 H49B 108.1 . . ? C51 C50 C49 110.7(7) . . ? C51 C50 H50A 109.5 . . ? C49 C50 H50A 109.5 . . ? C51 C50 H50B 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 108.1 . . ? C46 C51 C50 109.0(7) . . ? C46 C51 H51A 109.9 . . ? C50 C51 H51A 109.9 . . ? C46 C51 H51B 109.9 . . ? C50 C51 H51B 109.9 . . ? H51A C51 H51B 108.3 . . ? N45 C52 C57 112.2(7) . . ? N45 C52 C53 111.9(7) . . ? C57 C52 C53 111.0(8) . . ? N45 C52 H52A 107.1 . . ? C57 C52 H52A 107.1 . . ? C53 C52 H52A 107.1 . . ? C52 C53 C54 110.7(8) . . ? C52 C53 H53A 109.5 . . ? C54 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? C54 C53 H53B 109.5 . . ? H53A C53 H53B 108.1 . . ? C53 C54 C55 111.5(9) . . ? C53 C54 H54A 109.3 . . ? C55 C54 H54A 109.3 . . ? C53 C54 H54B 109.3 . . ? C55 C54 H54B 109.3 . . ? H54A C54 H54B 108.0 . . ? C56 C55 C54 110.5(8) . . ? C56 C55 H55A 109.6 . . ? C54 C55 H55A 109.6 . . ? C56 C55 H55B 109.6 . . ? C54 C55 H55B 109.6 . . ? H55A C55 H55B 108.1 . . ? C55 C56 C57 111.4(9) . . ? C55 C56 H56A 109.4 . . ? C57 C56 H56A 109.4 . . ? C55 C56 H56B 109.4 . . ? C57 C56 H56B 109.4 . . ? H56A C56 H56B 108.0 . . ? C52 C57 C56 111.0(8) . . ? C52 C57 H57A 109.4 . . ? C56 C57 H57A 109.4 . . ? C52 C57 H57B 109.4 . . ? C56 C57 H57B 109.4 . . ? H57A C57 H57B 108.0 . . ? N61 C61 C62 174.9(13) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C63A C64 C65 114(3) . . ? C65 C64 C63B 93(2) . . ? C65 C65 C64 117(3) 3_766 . ? 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 Cu2 C21 78.1(5) . . . . ? I1 Cu1 Cu2 C21 -137.0(3) . . . . ? C1 Cu1 Cu2 Cu3 -116.8(4) . . . . ? C21 Cu1 Cu2 Cu3 165.0(3) . . . . ? I1 Cu1 Cu2 Cu3 28.08(4) . . . . ? C1 Cu1 Cu2 I3 173.0(4) . . . . ? C21 Cu1 Cu2 I3 94.9(3) . . . . ? I1 Cu1 Cu2 I3 -42.11(9) . . . . ? C1 Cu1 Cu2 I2 -54.2(4) . . . . ? C21 Cu1 Cu2 I2 -132.4(3) . . . . ? I1 Cu1 Cu2 I2 90.66(4) . . . . ? C21 Cu2 Cu3 C41 -87.5(12) . . . . ? Cu1 Cu2 Cu3 C41 -119.8(10) . . . . ? I3 Cu2 Cu3 C41 24.2(10) . . . . ? I2 Cu2 Cu3 C41 149.4(10) . . . . ? C21 Cu2 Cu3 I2 123.2(6) . . . . ? Cu1 Cu2 Cu3 I2 90.85(5) . . . . ? I3 Cu2 Cu3 I2 -125.20(4) . . . . ? C21 Cu2 Cu3 I1 6.4(6) . . . . ? Cu1 Cu2 Cu3 I1 -25.97(4) . . . . ? I3 Cu2 Cu3 I1 117.98(4) . . . . ? I2 Cu2 Cu3 I1 -116.82(4) . . . . ? C21 Cu2 Cu3 I3 -111.6(6) . . . . ? Cu1 Cu2 Cu3 I3 -143.95(5) . . . . ? I2 Cu2 Cu3 I3 125.20(4) . . . . ? C1 Cu1 I1 Cu3 130.5(3) . . . . ? C21 Cu1 I1 Cu3 -59.9(2) . . . . ? Cu2 Cu1 I1 Cu3 -24.43(4) . . . . ? C41 Cu3 I1 Cu1 -170.5(3) . . . . ? Cu2 Cu3 I1 Cu1 24.28(4) . . . . ? I2 Cu3 I1 Cu1 -28.88(4) . . . . ? I3 Cu3 I1 Cu1 73.20(4) . . . . ? C21 Cu2 I2 Cu3 -154.1(3) . . . . ? Cu1 Cu2 I2 Cu3 -101.09(5) . . . . ? I3 Cu2 I2 Cu3 52.45(4) . . . . ? C41 Cu3 I2 Cu2 -170.5(3) . . . . ? I1 Cu3 I2 Cu2 61.34(4) . . . . ? I3 Cu3 I2 Cu2 -43.57(3) . . . . ? C21 Cu2 I3 Cu3 154.5(3) . . . . ? Cu1 Cu2 I3 Cu3 81.39(9) . . . . ? I2 Cu2 I3 Cu3 -48.91(4) . . . . ? C41 Cu3 I3 Cu2 -173.9(3) . . . . ? I2 Cu3 I3 Cu2 46.11(4) . . . . ? I1 Cu3 I3 Cu2 -59.79(4) . . . . ? C21 Cu1 C1 N2 123.6(6) . . . . ? Cu2 Cu1 C1 N2 67.2(8) . . . . ? I1 Cu1 C1 N2 -66.9(7) . . . . ? C21 Cu1 C1 N5 -54.3(8) . . . . ? Cu2 Cu1 C1 N5 -110.7(7) . . . . ? I1 Cu1 C1 N5 115.2(6) . . . . ? N5 C1 N2 C3 0.3(8) . . . . ? Cu1 C1 N2 C3 -178.1(6) . . . . ? N5 C1 N2 C6 -176.6(7) . . . . ? Cu1 C1 N2 C6 5.0(10) . . . . ? C1 N2 C3 C4 -0.1(9) . . . . ? C6 N2 C3 C4 176.6(7) . . . . ? N2 C3 C4 N5 -0.1(9) . . . . ? N2 C1 N5 C4 -0.3(8) . . . . ? Cu1 C1 N5 C4 178.0(6) . . . . ? N2 C1 N5 C12 173.5(7) . . . . ? Cu1 C1 N5 C12 -8.2(11) . . . . ? C3 C4 N5 C1 0.2(9) . . . . ? C3 C4 N5 C12 -173.4(7) . . . . ? C1 N2 C6 C7 98.6(9) . . . . ? C3 N2 C6 C7 -77.8(10) . . . . ? C1 N2 C6 C11 -136.8(8) . . . . ? C3 N2 C6 C11 46.8(11) . . . . ? N2 C6 C7 C8 -178.5(7) . . . . ? C11 C6 C7 C8 56.7(11) . . . . ? C6 C7 C8 C9 -56.4(12) . . . . ? C7 C8 C9 C10 55.9(12) . . . . ? C8 C9 C10 C11 -55.9(12) . . . . ? N2 C6 C11 C10 178.3(8) . . . . ? C7 C6 C11 C10 -56.9(11) . . . . ? C9 C10 C11 C6 56.2(12) . . . . ? C1 N5 C12 C13 148.7(8) . . . . ? C4 N5 C12 C13 -38.4(11) . . . . ? C1 N5 C12 C17 -87.3(9) . . . . ? C4 N5 C12 C17 85.6(9) . . . . ? N5 C12 C13 C14 179.9(7) . . . . ? C17 C12 C13 C14 56.3(10) . . . . ? C12 C13 C14 C15 -58.6(11) . . . . ? C13 C14 C15 C16 57.5(11) . . . . ? C14 C15 C16 C17 -54.2(10) . . . . ? C15 C16 C17 C12 52.6(10) . . . . ? N5 C12 C17 C16 -178.0(7) . . . . ? C13 C12 C17 C16 -53.7(10) . . . . ? Cu1 Cu2 C21 N25 106.2(7) . . . . ? Cu3 Cu2 C21 N25 68.0(10) . . . . ? I3 Cu2 C21 N25 -32.5(7) . . . . ? I2 Cu2 C21 N25 176.6(5) . . . . ? Cu1 Cu2 C21 N22 -108.8(7) . . . . ? Cu3 Cu2 C21 N22 -147.0(5) . . . . ? I3 Cu2 C21 N22 112.4(7) . . . . ? I2 Cu2 C21 N22 -38.4(8) . . . . ? Cu3 Cu2 C21 Cu1 -38.2(7) . . . . ? I3 Cu2 C21 Cu1 -138.76(12) . . . . ? I2 Cu2 C21 Cu1 70.4(3) . . . . ? C1 Cu1 C21 N25 99.7(6) . . . . ? Cu2 Cu1 C21 N25 -119.2(6) . . . . ? I1 Cu1 C21 N25 -71.3(6) . . . . ? C1 Cu1 C21 N22 -19.0(7) . . . . ? Cu2 Cu1 C21 N22 122.2(7) . . . . ? I1 Cu1 C21 N22 170.1(5) . . . . ? C1 Cu1 C21 Cu2 -141.1(3) . . . . ? I1 Cu1 C21 Cu2 47.9(3) . . . . ? N25 C21 N22 C23 -0.6(9) . . . . ? Cu2 C21 N22 C23 -151.0(6) . . . . ? Cu1 C21 N22 C23 123.0(6) . . . . ? N25 C21 N22 C26 173.9(6) . . . . ? Cu2 C21 N22 C26 23.5(11) . . . . ? Cu1 C21 N22 C26 -62.5(8) . . . . ? C21 N22 C23 C24 0.8(10) . . . . ? C26 N22 C23 C24 -173.4(7) . . . . ? N22 C23 C24 N25 -0.7(9) . . . . ? N22 C21 N25 C24 0.2(9) . . . . ? Cu2 C21 N25 C24 151.6(6) . . . . ? Cu1 C21 N25 C24 -125.0(6) . . . . ? N22 C21 N25 C32 -177.5(7) . . . . ? Cu2 C21 N25 C32 -26.0(10) . . . . ? Cu1 C21 N25 C32 57.4(8) . . . . ? C23 C24 N25 C21 0.3(9) . . . . ? C23 C24 N25 C32 177.9(7) . . . . ? C23 N22 C26 C31 81.5(9) . . . . ? C21 N22 C26 C31 -92.2(9) . . . . ? C23 N22 C26 C27 -44.9(11) . . . . ? C21 N22 C26 C27 141.4(7) . . . . ? N22 C26 C27 C28 179.0(7) . . . . ? C31 C26 C27 C28 54.2(10) . . . . ? C26 C27 C28 C29 -52.8(10) . . . . ? C27 C28 C29 C30 54.5(11) . . . . ? C28 C29 C30 C31 -55.0(11) . . . . ? N22 C26 C31 C30 177.5(7) . . . . ? C27 C26 C31 C30 -56.6(10) . . . . ? C29 C30 C31 C26 55.7(10) . . . . ? C21 N25 C32 C37 -113.0(9) . . . . ? C24 N25 C32 C37 69.7(10) . . . . ? C21 N25 C32 C33 121.4(8) . . . . ? C24 N25 C32 C33 -55.9(10) . . . . ? N25 C32 C33 C34 -174.4(7) . . . . ? C37 C32 C33 C34 60.3(10) . . . . ? C32 C33 C34 C35 -57.4(11) . . . . ? C33 C34 C35 C36 56.0(13) . . . . ? C34 C35 C36 C37 -55.6(13) . . . . ? N25 C32 C37 C36 175.2(8) . . . . ? C33 C32 C37 C36 -60.1(10) . . . . ? C35 C36 C37 C32 57.4(11) . . . . ? Cu2 Cu3 C41 N45 -156.0(6) . . . . ? I2 Cu3 C41 N45 -12.1(9) . . . . ? I1 Cu3 C41 N45 114.6(7) . . . . ? I3 Cu3 C41 N45 -134.6(7) . . . . ? Cu2 Cu3 C41 N42 29.4(16) . . . . ? I2 Cu3 C41 N42 173.3(5) . . . . ? I1 Cu3 C41 N42 -60.0(7) . . . . ? I3 Cu3 C41 N42 50.8(8) . . . . ? N45 C41 N42 C43 -1.0(9) . . . . ? Cu3 C41 N42 C43 174.7(6) . . . . ? N45 C41 N42 C46 178.5(7) . . . . ? Cu3 C41 N42 C46 -5.7(11) . . . . ? C41 N42 C43 C44 1.0(9) . . . . ? C46 N42 C43 C44 -178.6(7) . . . . ? N42 C43 C44 N45 -0.4(9) . . . . ? N42 C41 N45 C44 0.8(9) . . . . ? Cu3 C41 N45 C44 -174.7(6) . . . . ? N42 C41 N45 C52 179.2(7) . . . . ? Cu3 C41 N45 C52 3.7(12) . . . . ? C43 C44 N45 C41 -0.2(9) . . . . ? C43 C44 N45 C52 -178.5(7) . . . . ? C41 N42 C46 C47 -116.9(8) . . . . ? C43 N42 C46 C47 62.6(10) . . . . ? C41 N42 C46 C51 117.5(8) . . . . ? C43 N42 C46 C51 -63.0(10) . . . . ? N42 C46 C47 C48 177.0(7) . . . . ? C51 C46 C47 C48 -57.2(9) . . . . ? C46 C47 C48 C49 55.3(10) . . . . ? C47 C48 C49 C50 -55.7(10) . . . . ? C48 C49 C50 C51 58.0(10) . . . . ? N42 C46 C51 C50 -176.2(7) . . . . ? C47 C46 C51 C50 58.2(9) . . . . ? C49 C50 C51 C46 -58.3(10) . . . . ? C41 N45 C52 C57 141.6(8) . . . . ? C44 N45 C52 C57 -40.3(11) . . . . ? C41 N45 C52 C53 -92.9(9) . . . . ? C44 N45 C52 C53 85.2(10) . . . . ? N45 C52 C53 C54 178.0(8) . . . . ? C57 C52 C53 C54 -55.9(12) . . . . ? C52 C53 C54 C55 55.9(13) . . . . ? C53 C54 C55 C56 -56.3(13) . . . . ? C54 C55 C56 C57 55.9(12) . . . . ? N45 C52 C57 C56 -178.3(8) . . . . ? C53 C52 C57 C56 55.7(12) . . . . ? C55 C56 C57 C52 -56.4(13) . . . . ? C63B C63A C64 C65 -23(8) . . . . ? C63A C63B C64 C65 159(7) . . . . ? C63A C64 C65 C65 -176(3) . . . 3_766 ? C63B C64 C65 C65 175(3) . . . 3_766 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.561 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.166