#Supplementary Material (ESI) for Dalton Transactions #This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Victor N. Khrustalev' _publ_contact_author_email vkh@xray.ineos.ac.ru loop_ _publ_author_name E.Kolychev V.Shuntikov 'Victor N. Khrustalev' A.Bush M.Nechaev data_6DC21 _database_code_depnum_ccdc_archive 'CCDC 794664' #TrackingRef '6DC21.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 Br N2, 0.5(Br6 Cu2)' _chemical_formula_sum 'C28 H40 Br4 Cu N2' _chemical_formula_weight 787.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6908(10) _cell_length_b 10.7644(10) _cell_length_c 14.4174(14) _cell_angle_alpha 91.270(2) _cell_angle_beta 102.251(2) _cell_angle_gamma 106.937(2) _cell_volume 1544.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5246 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 32.64 _exptl_crystal_description prism _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 782 _exptl_absorpt_coefficient_mu 5.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.201 _exptl_absorpt_correction_T_max 0.347 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II 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 31556 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 32.75 _reflns_number_total 11257 _reflns_number_gt 8589 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL, v. 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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11257 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Br1 Br 1.01526(2) 0.56854(2) 0.388489(15) 0.01355(5) Uani 1 1 d . . . N1 N 0.91974(18) 0.58434(17) 0.19934(13) 0.0100(3) Uani 1 1 d . . . N2 N 0.75582(18) 0.53309(18) 0.28804(13) 0.0108(3) Uani 1 1 d . . . C1 C 0.8815(2) 0.5613(2) 0.27945(15) 0.0099(4) Uani 1 1 d . . . C2 C 0.8204(2) 0.5820(2) 0.10959(16) 0.0143(4) Uani 1 1 d . . . H2A H 0.8498 0.5514 0.0550 0.017 Uiso 1 1 calc R . . H2B H 0.8148 0.6712 0.1001 0.017 Uiso 1 1 calc R . . C3 C 0.6844(2) 0.4927(2) 0.11352(16) 0.0153(4) Uani 1 1 d . . . H3A H 0.6861 0.4012 0.1114 0.018 Uiso 1 1 calc R . . H3B H 0.6166 0.5011 0.0574 0.018 Uiso 1 1 calc R . . C4 C 0.6456(2) 0.5261(2) 0.20380(16) 0.0145(4) Uani 1 1 d . . . H4A H 0.6270 0.6109 0.2004 0.017 Uiso 1 1 calc R . . H4B H 0.5628 0.4587 0.2101 0.017 Uiso 1 1 calc R . . C5 C 1.0574(2) 0.6077(2) 0.19203(15) 0.0122(4) Uani 1 1 d . . . C6 C 1.1403(2) 0.7368(2) 0.19867(17) 0.0164(4) Uani 1 1 d . . . C7 C 1.2690(3) 0.7554(3) 0.18436(18) 0.0210(5) Uani 1 1 d . . . H7 H 1.3284 0.8415 0.1890 0.025 Uiso 1 1 calc R . . C8 C 1.3120(2) 0.6508(3) 0.16341(18) 0.0214(5) Uani 1 1 d . . . H8 H 1.3995 0.6660 0.1523 0.026 Uiso 1 1 calc R . . C9 C 1.2283(2) 0.5238(3) 0.15850(18) 0.0188(5) Uani 1 1 d . . . H9 H 1.2599 0.4530 0.1454 0.023 Uiso 1 1 calc R . . C10 C 1.0986(2) 0.4990(2) 0.17247(16) 0.0135(4) Uani 1 1 d . . . C11 C 1.0950(3) 0.8536(2) 0.22137(18) 0.0200(5) Uani 1 1 d . . . H11 H 1.0008 0.8195 0.2296 0.024 Uiso 1 1 calc R . . C12 C 1.1821(3) 0.9301(3) 0.3148(2) 0.0344(7) Uani 1 1 d . . . H12A H 1.1810 0.8715 0.3659 0.052 Uiso 1 1 calc R . . H12B H 1.1467 1.0002 0.3306 0.052 Uiso 1 1 calc R . . H12C H 1.2745 0.9676 0.3078 0.052 Uiso 1 1 calc R . . C13 C 1.0945(4) 0.9418(3) 0.1406(2) 0.0371(8) Uani 1 1 d . . . H13A H 1.0342 0.8919 0.0822 0.056 Uiso 1 1 calc R . . H13B H 1.1857 0.9756 0.1304 0.056 Uiso 1 1 calc R . . H13C H 1.0633 1.0146 0.1570 0.056 Uiso 1 1 calc R . . C14 C 1.0089(2) 0.3601(2) 0.16761(17) 0.0154(4) Uani 1 1 d . . . H14 H 0.9215 0.3629 0.1807 0.018 Uiso 1 1 calc R . . C15 C 1.0712(3) 0.2831(3) 0.24332(19) 0.0234(5) Uani 1 1 d . . . H15A H 1.0901 0.3289 0.3066 0.035 Uiso 1 1 calc R . . H15B H 1.1550 0.2757 0.2300 0.035 Uiso 1 1 calc R . . H15C H 1.0082 0.1958 0.2415 0.035 Uiso 1 1 calc R . . C16 C 0.9800(3) 0.2892(3) 0.06877(18) 0.0202(5) Uani 1 1 d . . . H16A H 0.9347 0.3350 0.0212 0.030 Uiso 1 1 calc R . . H16B H 0.9222 0.1997 0.0680 0.030 Uiso 1 1 calc R . . H16C H 1.0647 0.2875 0.0537 0.030 Uiso 1 1 calc R . . C17 C 0.7195(2) 0.5093(2) 0.37886(15) 0.0118(4) Uani 1 1 d . . . C18 C 0.6869(2) 0.3804(2) 0.40442(16) 0.0143(4) Uani 1 1 d . . . C19 C 0.6589(2) 0.3614(2) 0.49382(17) 0.0177(5) Uani 1 1 d . . . H19 H 0.6381 0.2759 0.5142 0.021 Uiso 1 1 calc R . . C20 C 0.6605(2) 0.4640(3) 0.55365(18) 0.0196(5) Uani 1 1 d . . . H20 H 0.6429 0.4487 0.6149 0.024 Uiso 1 1 calc R . . C21 C 0.6878(2) 0.5902(3) 0.52479(17) 0.0171(4) Uani 1 1 d . . . H21 H 0.6860 0.6596 0.5658 0.021 Uiso 1 1 calc R . . C22 C 0.7178(2) 0.6152(2) 0.43594(16) 0.0134(4) Uani 1 1 d . . . C23 C 0.6813(3) 0.2649(2) 0.33910(18) 0.0189(5) Uani 1 1 d . . . H23 H 0.6981 0.2981 0.2772 0.023 Uiso 1 1 calc R . . C24 C 0.7905(3) 0.2019(3) 0.3802(2) 0.0253(5) Uani 1 1 d . . . H24A H 0.8788 0.2680 0.3931 0.038 Uiso 1 1 calc R . . H24B H 0.7883 0.1325 0.3342 0.038 Uiso 1 1 calc R . . H24C H 0.7742 0.1649 0.4397 0.038 Uiso 1 1 calc R . . C25 C 0.5422(3) 0.1628(3) 0.3181(2) 0.0287(6) Uani 1 1 d . . . H25A H 0.4740 0.2031 0.2887 0.043 Uiso 1 1 calc R . . H25B H 0.5228 0.1290 0.3778 0.043 Uiso 1 1 calc R . . H25C H 0.5409 0.0910 0.2746 0.043 Uiso 1 1 calc R . . C26 C 0.7476(2) 0.7528(2) 0.40551(17) 0.0164(4) Uani 1 1 d . . . H26 H 0.7630 0.7496 0.3396 0.020 Uiso 1 1 calc R . . C27 C 0.8738(3) 0.8454(3) 0.4695(2) 0.0283(6) Uani 1 1 d . . . H27A H 0.9508 0.8144 0.4673 0.042 Uiso 1 1 calc R . . H27B H 0.8625 0.8485 0.5351 0.042 Uiso 1 1 calc R . . H27C H 0.8894 0.9328 0.4474 0.042 Uiso 1 1 calc R . . C28 C 0.6286(3) 0.8056(3) 0.4021(2) 0.0261(6) Uani 1 1 d . . . H28A H 0.5473 0.7441 0.3622 0.039 Uiso 1 1 calc R . . H28B H 0.6466 0.8900 0.3750 0.039 Uiso 1 1 calc R . . H28C H 0.6158 0.8165 0.4667 0.039 Uiso 1 1 calc R . . Cu1 Cu 0.60588(3) 0.90354(3) 0.02849(2) 0.01385(6) Uani 1 1 d . . . Br2 Br 0.64924(2) 0.74680(2) -0.065439(17) 0.01752(6) Uani 1 1 d . . . Br3 Br 0.74249(3) 0.89256(3) 0.176321(19) 0.02931(7) Uani 1 1 d . . . Br4 Br 0.62133(3) 1.12973(2) 0.06037(2) 0.02627(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.00862(10) 0.01985(11) 0.00998(10) 0.00091(8) 0.00084(7) 0.00189(8) N1 0.0086(8) 0.0109(8) 0.0094(8) 0.0005(6) 0.0016(6) 0.0018(7) N2 0.0090(8) 0.0116(8) 0.0106(8) 0.0008(6) 0.0025(6) 0.0010(7) C1 0.0085(9) 0.0080(9) 0.0107(9) -0.0012(7) -0.0005(7) 0.0010(7) C2 0.0129(10) 0.0158(10) 0.0112(10) 0.0012(8) -0.0005(8) 0.0021(8) C3 0.0125(10) 0.0148(10) 0.0147(10) -0.0007(8) -0.0019(8) 0.0020(8) C4 0.0089(9) 0.0164(10) 0.0151(10) 0.0004(8) -0.0010(8) 0.0021(8) C5 0.0095(9) 0.0167(10) 0.0101(9) 0.0006(8) 0.0043(7) 0.0021(8) C6 0.0179(11) 0.0147(10) 0.0148(10) -0.0006(8) 0.0053(9) 0.0012(9) C7 0.0155(11) 0.0204(12) 0.0227(12) -0.0021(9) 0.0085(9) -0.0041(9) C8 0.0111(11) 0.0282(13) 0.0243(13) 0.0012(10) 0.0087(9) 0.0021(10) C9 0.0162(11) 0.0243(12) 0.0178(11) -0.0002(9) 0.0062(9) 0.0075(10) C10 0.0129(10) 0.0148(10) 0.0126(10) 0.0005(8) 0.0039(8) 0.0032(8) C11 0.0217(12) 0.0116(10) 0.0243(12) -0.0030(9) 0.0094(10) -0.0014(9) C12 0.0331(16) 0.0300(15) 0.0333(16) -0.0158(12) 0.0092(13) -0.0006(13) C13 0.065(2) 0.0196(13) 0.0367(17) 0.0075(12) 0.0269(17) 0.0178(15) C14 0.0158(10) 0.0133(10) 0.0176(11) -0.0003(8) 0.0056(9) 0.0042(8) C15 0.0308(14) 0.0181(12) 0.0228(13) 0.0025(10) 0.0059(11) 0.0097(11) C16 0.0177(11) 0.0207(12) 0.0196(12) -0.0026(9) 0.0055(9) 0.0013(9) C17 0.0071(9) 0.0147(10) 0.0115(9) 0.0010(8) 0.0032(7) -0.0003(8) C18 0.0085(9) 0.0162(10) 0.0153(10) 0.0021(8) 0.0026(8) -0.0003(8) C19 0.0114(10) 0.0211(11) 0.0188(11) 0.0068(9) 0.0047(9) 0.0010(9) C20 0.0108(10) 0.0299(13) 0.0166(11) 0.0048(10) 0.0056(8) 0.0021(9) C21 0.0105(10) 0.0245(12) 0.0139(10) -0.0021(9) 0.0032(8) 0.0018(9) C22 0.0069(9) 0.0157(10) 0.0153(10) -0.0014(8) 0.0037(8) -0.0007(8) C23 0.0214(12) 0.0143(11) 0.0170(11) 0.0023(9) 0.0025(9) 0.0008(9) C24 0.0245(13) 0.0176(12) 0.0326(15) -0.0006(10) 0.0061(11) 0.0051(10) C25 0.0240(14) 0.0218(13) 0.0285(14) 0.0008(11) -0.0012(11) -0.0057(11) C26 0.0160(11) 0.0129(10) 0.0186(11) -0.0013(8) 0.0057(9) 0.0006(8) C27 0.0208(13) 0.0183(12) 0.0372(16) -0.0078(11) 0.0011(11) -0.0025(10) C28 0.0190(12) 0.0209(12) 0.0413(16) 0.0064(11) 0.0134(12) 0.0058(10) Cu1 0.01206(13) 0.01157(13) 0.01816(14) 0.00029(10) 0.00333(10) 0.00410(10) Br2 0.01560(11) 0.01685(11) 0.02020(12) -0.00331(8) 0.00204(9) 0.00688(9) Br3 0.04491(18) 0.02509(14) 0.01767(12) -0.00104(10) -0.00408(11) 0.01845(13) Br4 0.01503(12) 0.01370(11) 0.04486(17) -0.00648(10) -0.00449(11) 0.00514(9) _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 C1 1.870(2) . ? N1 C1 1.310(3) . ? N1 C5 1.446(3) . ? N1 C2 1.484(3) . ? N2 C1 1.322(3) . ? N2 C17 1.451(3) . ? N2 C4 1.485(3) . ? C2 C3 1.504(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.514(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.402(3) . ? C5 C10 1.407(3) . ? C6 C7 1.391(3) . ? C6 C11 1.525(3) . ? C7 C8 1.384(4) . ? C7 H7 0.9500 . ? C8 C9 1.390(4) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 C14 1.514(3) . ? C11 C13 1.519(4) . ? C11 C12 1.527(4) . ? C11 H11 1.0000 . ? 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 C16 1.529(3) . ? C14 C15 1.542(3) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C22 1.398(3) . ? C17 C18 1.407(3) . ? C18 C19 1.390(3) . ? C18 C23 1.522(3) . ? C19 C20 1.380(4) . ? C19 H19 0.9500 . ? C20 C21 1.396(4) . ? C20 H20 0.9500 . ? C21 C22 1.398(3) . ? C21 H21 0.9500 . ? C22 C26 1.517(3) . ? C23 C25 1.534(4) . ? C23 C24 1.537(4) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.521(3) . ? C26 C28 1.529(3) . ? C26 H26 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? Cu1 Br3 2.3410(4) . ? Cu1 Br2 2.3487(4) . ? Cu1 Br4 2.4129(4) 2_675 ? Cu1 Br4 2.4188(4) . ? Br4 Cu1 2.4129(4) 2_675 ? 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 N1 C5 122.79(18) . . ? C1 N1 C2 120.68(18) . . ? C5 N1 C2 116.47(17) . . ? C1 N2 C17 122.16(18) . . ? C1 N2 C4 120.59(18) . . ? C17 N2 C4 117.25(18) . . ? N1 C1 N2 124.57(19) . . ? N1 C1 Br1 117.13(16) . . ? N2 C1 Br1 118.30(16) . . ? N1 C2 C3 110.27(19) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 110.62(18) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 110.14(18) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C10 123.3(2) . . ? C6 C5 N1 118.8(2) . . ? C10 C5 N1 117.78(19) . . ? C7 C6 C5 117.0(2) . . ? C7 C6 C11 120.3(2) . . ? C5 C6 C11 122.7(2) . . ? C8 C7 C6 121.2(2) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C10 120.9(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 117.0(2) . . ? C9 C10 C14 120.3(2) . . ? C5 C10 C14 122.7(2) . . ? C13 C11 C6 111.7(2) . . ? C13 C11 C12 110.8(2) . . ? C6 C11 C12 110.9(2) . . ? C13 C11 H11 107.8 . . ? C6 C11 H11 107.8 . . ? C12 C11 H11 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 C16 111.5(2) . . ? C10 C14 C15 111.4(2) . . ? C16 C14 C15 109.6(2) . . ? C10 C14 H14 108.1 . . ? C16 C14 H14 108.1 . . ? C15 C14 H14 108.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 123.5(2) . . ? C22 C17 N2 118.40(19) . . ? C18 C17 N2 118.07(19) . . ? C19 C18 C17 116.8(2) . . ? C19 C18 C23 120.3(2) . . ? C17 C18 C23 123.0(2) . . ? C20 C19 C18 121.4(2) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 120.5(2) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 117.1(2) . . ? C17 C22 C26 122.9(2) . . ? C21 C22 C26 120.0(2) . . ? C18 C23 C25 111.4(2) . . ? C18 C23 C24 111.8(2) . . ? C25 C23 C24 110.3(2) . . ? C18 C23 H23 107.7 . . ? C25 C23 H23 107.7 . . ? C24 C23 H23 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 C27 112.1(2) . . ? C22 C26 C28 111.4(2) . . ? C27 C26 C28 110.0(2) . . ? C22 C26 H26 107.7 . . ? C27 C26 H26 107.7 . . ? C28 C26 H26 107.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Br3 Cu1 Br2 100.372(15) . . ? Br3 Cu1 Br4 145.550(18) . 2_675 ? Br2 Cu1 Br4 95.704(14) . 2_675 ? Br3 Cu1 Br4 94.337(14) . . ? Br2 Cu1 Br4 147.829(17) . . ? Br4 Cu1 Br4 87.713(13) 2_675 . ? Cu1 Br4 Cu1 92.287(13) 2_675 . ? 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 C5 N1 C1 N2 -176.5(2) . . . . ? C2 N1 C1 N2 0.9(3) . . . . ? C5 N1 C1 Br1 3.3(3) . . . . ? C2 N1 C1 Br1 -179.37(15) . . . . ? C17 N2 C1 N1 -179.6(2) . . . . ? C4 N2 C1 N1 -0.3(3) . . . . ? C17 N2 C1 Br1 0.7(3) . . . . ? C4 N2 C1 Br1 180.00(15) . . . . ? C1 N1 C2 C3 -27.3(3) . . . . ? C5 N1 C2 C3 150.21(19) . . . . ? N1 C2 C3 C4 51.5(2) . . . . ? C1 N2 C4 C3 26.0(3) . . . . ? C17 N2 C4 C3 -154.71(19) . . . . ? C2 C3 C4 N2 -50.8(3) . . . . ? C1 N1 C5 C6 -95.6(3) . . . . ? C2 N1 C5 C6 86.9(2) . . . . ? C1 N1 C5 C10 88.4(3) . . . . ? C2 N1 C5 C10 -89.1(2) . . . . ? C10 C5 C6 C7 0.4(4) . . . . ? N1 C5 C6 C7 -175.4(2) . . . . ? C10 C5 C6 C11 -179.1(2) . . . . ? N1 C5 C6 C11 5.1(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C11 C6 C7 C8 -179.8(2) . . . . ? C6 C7 C8 C9 -1.6(4) . . . . ? C7 C8 C9 C10 1.4(4) . . . . ? C8 C9 C10 C5 -0.3(4) . . . . ? C8 C9 C10 C14 -179.6(2) . . . . ? C6 C5 C10 C9 -0.6(3) . . . . ? N1 C5 C10 C9 175.3(2) . . . . ? C6 C5 C10 C14 178.7(2) . . . . ? N1 C5 C10 C14 -5.5(3) . . . . ? C7 C6 C11 C13 62.4(3) . . . . ? C5 C6 C11 C13 -118.2(3) . . . . ? C7 C6 C11 C12 -61.8(3) . . . . ? C5 C6 C11 C12 117.7(3) . . . . ? C9 C10 C14 C16 -62.4(3) . . . . ? C5 C10 C14 C16 118.3(2) . . . . ? C9 C10 C14 C15 60.2(3) . . . . ? C5 C10 C14 C15 -119.0(2) . . . . ? C1 N2 C17 C22 89.7(3) . . . . ? C4 N2 C17 C22 -89.6(2) . . . . ? C1 N2 C17 C18 -90.7(3) . . . . ? C4 N2 C17 C18 90.0(2) . . . . ? C22 C17 C18 C19 -3.5(3) . . . . ? N2 C17 C18 C19 176.9(2) . . . . ? C22 C17 C18 C23 176.4(2) . . . . ? N2 C17 C18 C23 -3.2(3) . . . . ? C17 C18 C19 C20 1.2(3) . . . . ? C23 C18 C19 C20 -178.6(2) . . . . ? C18 C19 C20 C21 1.4(4) . . . . ? C19 C20 C21 C22 -1.9(4) . . . . ? C18 C17 C22 C21 3.0(3) . . . . ? N2 C17 C22 C21 -177.43(19) . . . . ? C18 C17 C22 C26 -177.4(2) . . . . ? N2 C17 C22 C26 2.2(3) . . . . ? C20 C21 C22 C17 -0.2(3) . . . . ? C20 C21 C22 C26 -179.9(2) . . . . ? C19 C18 C23 C25 58.2(3) . . . . ? C17 C18 C23 C25 -121.7(2) . . . . ? C19 C18 C23 C24 -65.7(3) . . . . ? C17 C18 C23 C24 114.4(3) . . . . ? C17 C22 C26 C27 -115.8(3) . . . . ? C21 C22 C26 C27 63.8(3) . . . . ? C17 C22 C26 C28 120.3(2) . . . . ? C21 C22 C26 C28 -60.1(3) . . . . ? Br3 Cu1 Br4 Cu1 -145.550(18) . . . 2_675 ? Br2 Cu1 Br4 Cu1 97.08(3) . . . 2_675 ? Br4 Cu1 Br4 Cu1 0.0 2_675 . . 2_675 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 32.75 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.642 _refine_diff_density_min -1.437 _refine_diff_density_rms 0.134 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; # Attachment '6DC22.CIF' data_6DC22 _database_code_depnum_ccdc_archive 'CCDC 794665' #TrackingRef '6DC22.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 Br N2, Br2 Cu' _chemical_formula_sum 'C28 H40 Br3 Cu N2' _chemical_formula_weight 707.89 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 19.4962(9) _cell_length_b 19.3988(9) _cell_length_c 15.5513(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.8270(10) _cell_angle_gamma 90.00 _cell_volume 5878.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5516 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2848 _exptl_absorpt_coefficient_mu 4.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.325 _exptl_absorpt_correction_T_max 0.444 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II 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 65975 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.97 _reflns_number_total 14107 _reflns_number_gt 10102 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL, v. 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^)+(0.0269P)^2^+4.9900P] 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 14107 _refine_ls_number_parameters 605 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.487166(15) 0.706144(14) 0.437312(17) 0.01804(6) Uani 1 1 d . . . N1 N 0.51780(11) 0.70472(11) 0.61146(14) 0.0143(5) Uani 1 1 d . . . N2 N 0.52491(11) 0.81203(12) 0.54642(14) 0.0149(5) Uani 1 1 d . . . C1 C 0.51379(13) 0.74516(14) 0.54360(17) 0.0144(6) Uani 1 1 d . . . C2 C 0.52845(15) 0.73470(15) 0.69846(17) 0.0176(6) Uani 1 1 d . . . H2A H 0.5501 0.7001 0.7375 0.021 Uiso 1 1 calc R . . H2B H 0.4837 0.7479 0.7219 0.021 Uiso 1 1 calc R . . C3 C 0.57387(15) 0.79727(15) 0.69338(18) 0.0204(6) Uani 1 1 d . . . H3A H 0.6204 0.7831 0.6767 0.024 Uiso 1 1 calc R . . H3B H 0.5778 0.8196 0.7505 0.024 Uiso 1 1 calc R . . C4 C 0.54454(15) 0.84799(15) 0.62806(18) 0.0192(6) Uani 1 1 d . . . H4A H 0.5037 0.8708 0.6514 0.023 Uiso 1 1 calc R . . H4B H 0.5791 0.8840 0.6166 0.023 Uiso 1 1 calc R . . C5 C 0.50673(14) 0.63063(14) 0.60755(17) 0.0151(6) Uani 1 1 d . . . C6 C 0.44016(15) 0.60595(15) 0.61142(17) 0.0174(6) Uani 1 1 d . . . C7 C 0.43238(16) 0.53459(15) 0.61332(18) 0.0221(7) Uani 1 1 d . . . H7A H 0.3877 0.5154 0.6162 0.027 Uiso 1 1 calc R . . C8 C 0.48812(17) 0.49144(16) 0.61108(19) 0.0266(7) Uani 1 1 d . . . H8A H 0.4814 0.4429 0.6122 0.032 Uiso 1 1 calc R . . C9 C 0.55387(17) 0.51765(15) 0.60720(18) 0.0234(7) Uani 1 1 d . . . H9A H 0.5918 0.4870 0.6055 0.028 Uiso 1 1 calc R . . C10 C 0.56512(15) 0.58828(14) 0.60571(17) 0.0173(6) Uani 1 1 d . . . C11 C 0.37806(14) 0.65253(15) 0.61718(19) 0.0201(6) Uani 1 1 d . . . H11A H 0.3932 0.7008 0.6057 0.024 Uiso 1 1 calc R . . C12 C 0.34992(16) 0.65048(16) 0.7079(2) 0.0253(7) Uani 1 1 d . . . H12A H 0.3860 0.6645 0.7497 0.038 Uiso 1 1 calc R . . H12B H 0.3349 0.6035 0.7209 0.038 Uiso 1 1 calc R . . H12C H 0.3109 0.6821 0.7111 0.038 Uiso 1 1 calc R . . C13 C 0.32219(16) 0.63410(18) 0.5502(2) 0.0299(7) Uani 1 1 d . . . H13A H 0.3413 0.6355 0.4927 0.045 Uiso 1 1 calc R . . H13B H 0.2845 0.6673 0.5533 0.045 Uiso 1 1 calc R . . H13C H 0.3049 0.5877 0.5616 0.045 Uiso 1 1 calc R . . C14 C 0.63704(17) 0.6178(2) 0.6024(2) 0.0378(5) Uani 1 1 d . . . H14A H 0.6369 0.6628 0.6336 0.045 Uiso 1 1 calc R . . C15 C 0.65781(17) 0.6324(2) 0.5112(2) 0.0378(5) Uani 1 1 d . . . H15A H 0.6237 0.6626 0.4830 0.057 Uiso 1 1 calc R . . H15B H 0.6605 0.5889 0.4793 0.057 Uiso 1 1 calc R . . H15C H 0.7027 0.6550 0.5123 0.057 Uiso 1 1 calc R . . C16 C 0.69158(17) 0.5730(2) 0.6458(2) 0.0378(5) Uani 1 1 d . . . H16A H 0.6779 0.5617 0.7042 0.057 Uiso 1 1 calc R . . H16B H 0.7353 0.5980 0.6485 0.057 Uiso 1 1 calc R . . H16C H 0.6969 0.5305 0.6127 0.057 Uiso 1 1 calc R . . C17 C 0.51834(14) 0.85616(14) 0.47125(17) 0.0157(6) Uani 1 1 d . . . C18 C 0.57727(14) 0.86978(14) 0.42593(18) 0.0177(6) Uani 1 1 d . . . C19 C 0.57044(15) 0.91530(15) 0.35689(18) 0.0208(6) Uani 1 1 d . . . H19A H 0.6094 0.9259 0.3243 0.025 Uiso 1 1 calc R . . C20 C 0.50817(16) 0.94523(15) 0.33497(19) 0.0218(6) Uani 1 1 d . . . H20A H 0.5048 0.9766 0.2881 0.026 Uiso 1 1 calc R . . C21 C 0.45070(15) 0.92985(15) 0.38092(19) 0.0219(6) Uani 1 1 d . . . H21A H 0.4080 0.9504 0.3646 0.026 Uiso 1 1 calc R . . C22 C 0.45407(15) 0.88482(14) 0.45076(18) 0.0183(6) Uani 1 1 d . . . C23 C 0.64663(14) 0.83678(15) 0.4481(2) 0.0221(7) Uani 1 1 d . . . H23A H 0.6398 0.8036 0.4962 0.027 Uiso 1 1 calc R . . C24 C 0.67371(17) 0.79594(18) 0.3722(2) 0.0338(8) Uani 1 1 d . . . H24A H 0.6395 0.7617 0.3533 0.051 Uiso 1 1 calc R . . H24B H 0.7163 0.7725 0.3900 0.051 Uiso 1 1 calc R . . H24C H 0.6827 0.8275 0.3246 0.051 Uiso 1 1 calc R . . C25 C 0.69958(16) 0.88980(17) 0.4792(2) 0.0287(7) Uani 1 1 d . . . H25A H 0.6827 0.9137 0.5299 0.043 Uiso 1 1 calc R . . H25B H 0.7072 0.9233 0.4334 0.043 Uiso 1 1 calc R . . H25C H 0.7429 0.8664 0.4944 0.043 Uiso 1 1 calc R . . C26 C 0.38981(15) 0.86775(15) 0.49937(19) 0.0211(6) Uani 1 1 d . . . H26A H 0.4039 0.8397 0.5509 0.025 Uiso 1 1 calc R . . C27 C 0.35548(16) 0.93309(16) 0.5309(2) 0.0271(7) Uani 1 1 d . . . H27A H 0.3157 0.9208 0.5647 0.041 Uiso 1 1 calc R . . H27B H 0.3403 0.9611 0.4814 0.041 Uiso 1 1 calc R . . H27C H 0.3883 0.9595 0.5668 0.041 Uiso 1 1 calc R . . C28 C 0.33895(15) 0.82521(16) 0.4451(2) 0.0263(7) Uani 1 1 d . . . H28A H 0.2998 0.8126 0.4799 0.039 Uiso 1 1 calc R . . H28B H 0.3616 0.7833 0.4252 0.039 Uiso 1 1 calc R . . H28C H 0.3228 0.8524 0.3953 0.039 Uiso 1 1 calc R . . Br2 Br 0.014254(15) 0.483021(14) 0.359329(18) 0.01833(6) Uani 1 1 d . . . N3 N 0.00597(11) 0.61769(11) 0.30412(14) 0.0139(5) Uani 1 1 d . . . N4 N -0.02008(11) 0.53503(11) 0.19973(14) 0.0148(5) Uani 1 1 d . . . C29 C -0.00146(13) 0.55324(14) 0.27840(17) 0.0134(5) Uani 1 1 d . . . C30 C -0.00298(15) 0.67624(14) 0.24313(18) 0.0188(6) Uani 1 1 d . . . H30A H 0.0317 0.7121 0.2570 0.023 Uiso 1 1 calc R . . H30B H -0.0490 0.6968 0.2495 0.023 Uiso 1 1 calc R . . C31 C 0.00460(16) 0.65249(15) 0.15156(18) 0.0209(6) Uani 1 1 d . . . H31A H 0.0534 0.6421 0.1414 0.025 Uiso 1 1 calc R . . H31B H -0.0104 0.6896 0.1114 0.025 Uiso 1 1 calc R . . C32 C -0.03839(16) 0.58884(15) 0.13513(19) 0.0214(6) Uani 1 1 d . . . H32A H -0.0876 0.6006 0.1387 0.026 Uiso 1 1 calc R . . H32B H -0.0304 0.5711 0.0766 0.026 Uiso 1 1 calc R . . C33 C 0.01591(14) 0.63621(13) 0.39421(17) 0.0145(6) Uani 1 1 d . . . C34 C -0.04243(14) 0.64214(14) 0.44337(18) 0.0164(6) Uani 1 1 d . . . C35 C -0.03212(15) 0.66208(14) 0.52929(18) 0.0181(6) Uani 1 1 d . . . H35A H -0.0704 0.6674 0.5650 0.022 Uiso 1 1 calc R . . C36 C 0.03349(15) 0.67418(14) 0.56274(18) 0.0197(6) Uani 1 1 d . . . H36A H 0.0398 0.6871 0.6214 0.024 Uiso 1 1 calc R . . C37 C 0.08976(15) 0.66761(14) 0.51178(18) 0.0193(6) Uani 1 1 d . . . H37A H 0.1343 0.6760 0.5361 0.023 Uiso 1 1 calc R . . C38 C 0.08265(14) 0.64898(13) 0.42546(17) 0.0144(6) Uani 1 1 d . . . C39 C -0.11472(14) 0.62822(15) 0.40829(19) 0.0196(6) Uani 1 1 d . . . H39A H -0.1113 0.6116 0.3477 0.024 Uiso 1 1 calc R . . C40 C -0.15008(16) 0.57160(17) 0.4601(2) 0.0293(7) Uani 1 1 d . . . H40A H -0.1206 0.5307 0.4633 0.044 Uiso 1 1 calc R . . H40B H -0.1940 0.5596 0.4316 0.044 Uiso 1 1 calc R . . H40C H -0.1581 0.5884 0.5183 0.044 Uiso 1 1 calc R . . C41 C -0.15738(16) 0.69398(16) 0.4067(2) 0.0265(7) Uani 1 1 d . . . H41A H -0.1356 0.7284 0.3705 0.040 Uiso 1 1 calc R . . H41B H -0.1605 0.7119 0.4654 0.040 Uiso 1 1 calc R . . H41C H -0.2036 0.6839 0.3833 0.040 Uiso 1 1 calc R . . C42 C 0.14559(14) 0.64189(14) 0.37077(19) 0.0185(6) Uani 1 1 d . . . H42A H 0.1295 0.6364 0.3095 0.022 Uiso 1 1 calc R . . C43 C 0.19143(15) 0.70596(15) 0.3766(2) 0.0244(7) Uani 1 1 d . . . H43A H 0.1681 0.7447 0.3476 0.037 Uiso 1 1 calc R . . H43B H 0.2348 0.6966 0.3487 0.037 Uiso 1 1 calc R . . H43C H 0.2007 0.7176 0.4372 0.037 Uiso 1 1 calc R . . C44 C 0.18721(16) 0.57762(16) 0.3963(2) 0.0274(7) Uani 1 1 d . . . H44A H 0.1587 0.5365 0.3874 0.041 Uiso 1 1 calc R . . H44B H 0.2018 0.5808 0.4571 0.041 Uiso 1 1 calc R . . H44C H 0.2277 0.5745 0.3608 0.041 Uiso 1 1 calc R . . C45 C -0.01701(15) 0.46447(14) 0.16907(18) 0.0173(6) Uani 1 1 d . . . C46 C 0.04593(15) 0.43964(15) 0.14247(19) 0.0211(6) Uani 1 1 d . . . C47 C 0.04609(18) 0.37452(16) 0.1047(2) 0.0301(8) Uani 1 1 d . . . H47A H 0.0881 0.3557 0.0861 0.036 Uiso 1 1 calc R . . C48 C -0.0133(2) 0.33718(17) 0.0940(2) 0.0362(9) Uani 1 1 d . . . H48A H -0.0122 0.2932 0.0671 0.043 Uiso 1 1 calc R . . C49 C -0.0744(2) 0.36305(17) 0.1218(2) 0.0366(9) Uani 1 1 d . . . H49A H -0.1150 0.3365 0.1138 0.044 Uiso 1 1 calc R . . C50 C -0.07816(16) 0.42725(15) 0.1615(2) 0.0236(7) Uani 1 1 d . . . C51 C 0.11190(15) 0.48006(17) 0.1522(2) 0.0271(7) Uani 1 1 d . . . H51A H 0.1019 0.5228 0.1854 0.033 Uiso 1 1 calc R . . C52 C 0.16708(18) 0.4403(2) 0.2024(2) 0.0454(10) Uani 1 1 d . . . H52A H 0.1497 0.4268 0.2584 0.068 Uiso 1 1 calc R . . H52B H 0.2077 0.4695 0.2111 0.068 Uiso 1 1 calc R . . H52C H 0.1794 0.3990 0.1701 0.068 Uiso 1 1 calc R . . C53 C 0.13726(17) 0.50214(19) 0.0645(2) 0.0349(8) Uani 1 1 d . . . H53A H 0.1011 0.5283 0.0337 0.052 Uiso 1 1 calc R . . H53B H 0.1488 0.4612 0.0310 0.052 Uiso 1 1 calc R . . H53C H 0.1781 0.5312 0.0724 0.052 Uiso 1 1 calc R . . C54 C -0.14523(18) 0.4529(2) 0.1974(2) 0.0426(5) Uani 1 1 d . . . H54A H -0.1391 0.5027 0.2129 0.051 Uiso 1 1 calc R . . C55 C -0.16228(18) 0.4137(2) 0.2793(2) 0.0426(5) Uani 1 1 d . . . H55A H -0.1237 0.4172 0.3209 0.064 Uiso 1 1 calc R . . H55B H -0.1707 0.3651 0.2653 0.064 Uiso 1 1 calc R . . H55C H -0.2034 0.4337 0.3041 0.064 Uiso 1 1 calc R . . C56 C -0.20521(18) 0.4476(2) 0.1336(2) 0.0426(5) Uani 1 1 d . . . H56A H -0.1981 0.4790 0.0854 0.064 Uiso 1 1 calc R . . H56B H -0.2476 0.4601 0.1620 0.064 Uiso 1 1 calc R . . H56C H -0.2088 0.4002 0.1122 0.064 Uiso 1 1 calc R . . Cu1 Cu 0.291942(19) 0.66928(2) 0.19970(2) 0.02439(9) Uani 1 1 d . . . Br3 Br 0.389967(16) 0.640185(17) 0.269535(19) 0.02564(7) Uani 1 1 d . . . Br4 Br 0.193153(16) 0.695939(19) 0.13047(2) 0.03297(8) Uani 1 1 d . . . Cu2 Cu 0.24035(2) 0.34745(2) 0.79349(3) 0.03107(10) Uani 1 1 d . . . Br5 Br 0.305101(19) 0.42782(2) 0.73405(3) 0.04424(10) Uani 1 1 d . . . Br6 Br 0.176588(19) 0.26616(2) 0.85264(3) 0.04555(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02475(15) 0.01402(14) 0.01518(13) -0.00114(11) -0.00182(11) 0.00078(12) N1 0.0140(11) 0.0132(11) 0.0153(11) 0.0009(9) -0.0023(9) 0.0000(10) N2 0.0150(12) 0.0132(12) 0.0162(12) -0.0004(9) -0.0021(9) -0.0001(9) C1 0.0113(13) 0.0153(14) 0.0164(14) -0.0020(11) -0.0013(11) -0.0001(11) C2 0.0207(15) 0.0188(15) 0.0133(13) -0.0013(11) -0.0017(11) 0.0003(12) C3 0.0240(15) 0.0192(15) 0.0177(14) -0.0006(12) -0.0030(12) -0.0028(13) C4 0.0208(15) 0.0153(14) 0.0211(15) -0.0008(12) -0.0020(12) -0.0037(12) C5 0.0199(14) 0.0116(13) 0.0137(13) -0.0015(11) -0.0012(11) 0.0031(11) C6 0.0217(15) 0.0173(14) 0.0130(13) 0.0002(11) -0.0022(11) -0.0012(12) C7 0.0300(17) 0.0190(15) 0.0174(15) -0.0004(12) -0.0003(13) -0.0037(13) C8 0.048(2) 0.0133(15) 0.0188(15) -0.0007(12) 0.0015(14) -0.0025(14) C9 0.0353(18) 0.0176(15) 0.0173(15) -0.0003(12) 0.0025(13) 0.0099(14) C10 0.0209(15) 0.0185(15) 0.0123(13) 0.0004(11) 0.0001(11) 0.0062(12) C11 0.0149(14) 0.0205(15) 0.0246(15) 0.0019(12) -0.0028(12) -0.0005(12) C12 0.0215(16) 0.0259(17) 0.0285(17) 0.0013(14) 0.0010(13) 0.0002(13) C13 0.0228(16) 0.0345(19) 0.0318(18) -0.0015(15) -0.0072(14) -0.0011(15) C14 0.0222(10) 0.0520(14) 0.0392(12) 0.0107(10) 0.0020(9) 0.0087(10) C15 0.0222(10) 0.0520(14) 0.0392(12) 0.0107(10) 0.0020(9) 0.0087(10) C16 0.0222(10) 0.0520(14) 0.0392(12) 0.0107(10) 0.0020(9) 0.0087(10) C17 0.0192(14) 0.0120(13) 0.0158(13) -0.0004(11) -0.0025(11) -0.0005(11) C18 0.0188(14) 0.0141(14) 0.0201(15) -0.0046(11) -0.0010(12) -0.0021(12) C19 0.0221(15) 0.0197(15) 0.0206(15) 0.0009(12) 0.0022(12) -0.0046(13) C20 0.0293(17) 0.0168(15) 0.0191(15) 0.0022(12) -0.0048(13) -0.0013(13) C21 0.0205(15) 0.0199(15) 0.0250(16) 0.0004(13) -0.0057(13) 0.0013(13) C22 0.0217(15) 0.0139(14) 0.0190(14) -0.0023(11) -0.0021(12) -0.0011(12) C23 0.0177(15) 0.0212(16) 0.0274(16) 0.0064(13) -0.0002(13) 0.0006(12) C24 0.0271(18) 0.034(2) 0.040(2) -0.0059(16) 0.0013(15) 0.0087(16) C25 0.0192(16) 0.0294(18) 0.0373(19) 0.0023(15) -0.0045(14) -0.0007(14) C26 0.0179(15) 0.0195(15) 0.0256(16) 0.0022(13) -0.0006(12) 0.0047(12) C27 0.0230(16) 0.0253(17) 0.0329(18) -0.0062(14) 0.0000(14) 0.0050(14) C28 0.0192(15) 0.0258(17) 0.0342(18) -0.0055(14) 0.0039(13) -0.0008(13) Br2 0.02377(15) 0.01364(13) 0.01745(14) 0.00290(11) -0.00126(11) 0.00073(12) N3 0.0154(12) 0.0116(11) 0.0145(11) 0.0008(9) -0.0019(9) 0.0003(9) N4 0.0162(12) 0.0115(11) 0.0165(12) -0.0003(9) -0.0026(9) -0.0006(9) C29 0.0091(12) 0.0144(14) 0.0166(13) 0.0032(11) -0.0023(11) 0.0002(11) C30 0.0252(15) 0.0117(14) 0.0191(14) 0.0034(11) -0.0051(12) -0.0017(12) C31 0.0251(16) 0.0185(15) 0.0188(15) 0.0051(12) -0.0043(12) -0.0034(13) C32 0.0261(16) 0.0169(15) 0.0207(15) 0.0028(12) -0.0073(13) -0.0012(13) C33 0.0197(14) 0.0094(13) 0.0142(13) 0.0001(11) -0.0009(11) 0.0019(11) C34 0.0176(14) 0.0101(13) 0.0216(14) 0.0025(11) 0.0010(12) 0.0038(11) C35 0.0223(15) 0.0148(14) 0.0177(14) 0.0015(11) 0.0064(12) 0.0047(12) C36 0.0304(17) 0.0144(14) 0.0141(14) -0.0016(11) -0.0035(12) 0.0034(13) C37 0.0198(15) 0.0157(14) 0.0220(15) -0.0007(12) -0.0041(12) 0.0015(12) C38 0.0152(13) 0.0100(13) 0.0179(14) 0.0010(11) -0.0011(11) 0.0012(11) C39 0.0132(14) 0.0237(16) 0.0218(15) -0.0007(12) -0.0001(12) 0.0025(12) C40 0.0174(15) 0.0318(18) 0.0385(19) 0.0073(15) 0.0000(14) -0.0046(14) C41 0.0214(16) 0.0307(18) 0.0273(16) 0.0004(14) -0.0017(13) 0.0090(14) C42 0.0154(14) 0.0176(14) 0.0224(15) -0.0023(12) -0.0009(12) -0.0004(12) C43 0.0227(16) 0.0190(15) 0.0316(17) -0.0009(13) 0.0039(13) -0.0009(13) C44 0.0185(15) 0.0207(16) 0.043(2) 0.0000(15) 0.0027(14) 0.0030(13) C45 0.0215(15) 0.0143(14) 0.0159(14) -0.0012(11) -0.0034(12) -0.0023(12) C46 0.0235(16) 0.0198(15) 0.0200(15) 0.0007(12) 0.0005(12) 0.0013(13) C47 0.042(2) 0.0196(17) 0.0292(18) -0.0011(14) 0.0076(15) 0.0065(15) C48 0.060(3) 0.0173(16) 0.0310(19) -0.0044(14) 0.0045(18) -0.0035(17) C49 0.047(2) 0.0246(18) 0.038(2) -0.0008(16) -0.0018(17) -0.0188(17) C50 0.0269(17) 0.0187(15) 0.0250(16) 0.0010(13) -0.0027(13) -0.0080(13) C51 0.0187(15) 0.0322(18) 0.0303(17) -0.0073(15) 0.0007(13) 0.0046(14) C52 0.0277(19) 0.076(3) 0.033(2) 0.000(2) 0.0014(16) 0.013(2) C53 0.0279(18) 0.041(2) 0.0358(19) -0.0027(16) 0.0018(15) -0.0036(16) C54 0.0273(11) 0.0616(15) 0.0389(12) 0.0036(11) -0.0006(9) -0.0080(11) C55 0.0273(11) 0.0616(15) 0.0389(12) 0.0036(11) -0.0006(9) -0.0080(11) C56 0.0273(11) 0.0616(15) 0.0389(12) 0.0036(11) -0.0006(9) -0.0080(11) Cu1 0.01976(19) 0.0283(2) 0.0249(2) 0.00476(16) -0.00146(15) 0.00004(16) Br3 0.02226(15) 0.03109(17) 0.02331(16) 0.00302(13) -0.00332(12) -0.00128(13) Br4 0.02239(16) 0.0418(2) 0.03440(18) 0.01057(15) -0.00331(14) 0.00134(15) Cu2 0.0221(2) 0.0374(2) 0.0336(2) 0.01196(19) -0.00059(17) 0.00173(18) Br5 0.0332(2) 0.0375(2) 0.0620(3) 0.02332(19) 0.00141(18) 0.00156(17) Br6 0.02997(19) 0.0596(3) 0.0469(2) 0.0263(2) -0.00143(17) -0.00678(18) _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 C1 1.876(3) . ? N1 C1 1.315(3) . ? N1 C5 1.454(3) . ? N1 C2 1.481(3) . ? N2 C1 1.316(3) . ? N2 C17 1.451(3) . ? N2 C4 1.488(3) . ? C2 C3 1.506(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.387(4) . ? C5 C10 1.405(4) . ? C6 C7 1.393(4) . ? C6 C11 1.516(4) . ? C7 C8 1.373(4) . ? C7 H7A 0.9500 . ? C8 C9 1.382(4) . ? C8 H8A 0.9500 . ? C9 C10 1.388(4) . ? C9 H9A 0.9500 . ? C10 C14 1.517(4) . ? C11 C13 1.525(4) . ? C11 C12 1.530(4) . ? C11 H11A 1.0000 . ? 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 C15 1.513(5) . ? C14 C16 1.515(5) . ? C14 H14A 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.392(4) . ? C17 C22 1.398(4) . ? C18 C19 1.393(4) . ? C18 C23 1.526(4) . ? C19 C20 1.379(4) . ? C19 H19A 0.9500 . ? C20 C21 1.381(4) . ? C20 H20A 0.9500 . ? C21 C22 1.394(4) . ? C21 H21A 0.9500 . ? C22 C26 1.520(4) . ? C23 C25 1.525(4) . ? C23 C24 1.529(4) . ? C23 H23A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.522(4) . ? C26 C28 1.524(4) . ? C26 H26A 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? Br2 C29 1.873(3) . ? N3 C29 1.319(3) . ? N3 C33 1.453(3) . ? N3 C30 1.486(3) . ? N4 C29 1.313(3) . ? N4 C45 1.451(3) . ? N4 C32 1.484(3) . ? C30 C31 1.508(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.509(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.395(4) . ? C33 C38 1.397(4) . ? C34 C35 1.399(4) . ? C34 C39 1.519(4) . ? C35 C36 1.386(4) . ? C35 H35A 0.9500 . ? C36 C37 1.380(4) . ? C36 H36A 0.9500 . ? C37 C38 1.393(4) . ? C37 H37A 0.9500 . ? C38 C42 1.521(4) . ? C39 C41 1.523(4) . ? C39 C40 1.538(4) . ? C39 H39A 1.0000 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.532(4) . ? C42 C44 1.533(4) . ? C42 H42A 1.0000 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.393(4) . ? C45 C50 1.396(4) . ? C46 C47 1.393(4) . ? C46 C51 1.510(4) . ? C47 C48 1.371(5) . ? C47 H47A 0.9500 . ? C48 C49 1.375(5) . ? C48 H48A 0.9500 . ? C49 C50 1.393(4) . ? C49 H49A 0.9500 . ? C50 C54 1.522(5) . ? C51 C52 1.519(5) . ? C51 C53 1.528(5) . ? C51 H51A 1.0000 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 C56 1.513(5) . ? C54 C55 1.529(5) . ? C54 H54A 1.0000 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? Cu1 Br4 2.2370(5) . ? Cu1 Br3 2.2401(5) . ? Cu2 Br6 2.2250(5) . ? Cu2 Br5 2.2257(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 123.4(2) . . ? C1 N1 C2 120.1(2) . . ? C5 N1 C2 116.3(2) . . ? C1 N2 C17 123.0(2) . . ? C1 N2 C4 121.9(2) . . ? C17 N2 C4 115.1(2) . . ? N1 C1 N2 123.8(2) . . ? N1 C1 Br1 118.3(2) . . ? N2 C1 Br1 117.9(2) . . ? N1 C2 C3 109.5(2) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 110.4(2) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 110.5(2) . . ? N2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C10 124.0(3) . . ? C6 C5 N1 118.5(2) . . ? C10 C5 N1 117.4(2) . . ? C5 C6 C7 116.5(3) . . ? C5 C6 C11 123.2(3) . . ? C7 C6 C11 120.2(3) . . ? C8 C7 C6 121.2(3) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9A 119.6 . . ? C10 C9 H9A 119.6 . . ? C9 C10 C5 116.6(3) . . ? C9 C10 C14 121.3(3) . . ? C5 C10 C14 122.0(3) . . ? C6 C11 C13 112.0(2) . . ? C6 C11 C12 110.5(2) . . ? C13 C11 C12 110.7(2) . . ? C6 C11 H11A 107.8 . . ? C13 C11 H11A 107.8 . . ? C12 C11 H11A 107.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C16 108.6(3) . . ? C15 C14 C10 112.2(3) . . ? C16 C14 C10 113.9(3) . . ? C15 C14 H14A 107.3 . . ? C16 C14 H14A 107.3 . . ? C10 C14 H14A 107.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 123.9(3) . . ? C18 C17 N2 117.8(2) . . ? C22 C17 N2 118.3(2) . . ? C17 C18 C19 116.8(3) . . ? C17 C18 C23 123.1(3) . . ? C19 C18 C23 120.1(3) . . ? C20 C19 C18 121.3(3) . . ? C20 C19 H19A 119.4 . . ? C18 C19 H19A 119.4 . . ? C19 C20 C21 120.2(3) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C22 121.3(3) . . ? C20 C21 H21A 119.3 . . ? C22 C21 H21A 119.3 . . ? C21 C22 C17 116.5(3) . . ? C21 C22 C26 120.3(3) . . ? C17 C22 C26 123.1(3) . . ? C18 C23 C25 112.0(2) . . ? C18 C23 C24 111.6(3) . . ? C25 C23 C24 110.3(3) . . ? C18 C23 H23A 107.5 . . ? C25 C23 H23A 107.5 . . ? C24 C23 H23A 107.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 C27 110.9(2) . . ? C22 C26 C28 112.0(2) . . ? C27 C26 C28 110.1(2) . . ? C22 C26 H26A 107.9 . . ? C27 C26 H26A 107.9 . . ? C28 C26 H26A 107.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C29 N3 C33 122.5(2) . . ? C29 N3 C30 121.4(2) . . ? C33 N3 C30 115.8(2) . . ? C29 N4 C45 123.1(2) . . ? C29 N4 C32 119.6(2) . . ? C45 N4 C32 116.9(2) . . ? N4 C29 N3 124.2(2) . . ? N4 C29 Br2 117.7(2) . . ? N3 C29 Br2 118.13(19) . . ? N3 C30 C31 110.8(2) . . ? N3 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? N3 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C30 C31 C32 109.8(2) . . ? C30 C31 H31A 109.7 . . ? C32 C31 H31A 109.7 . . ? C30 C31 H31B 109.7 . . ? C32 C31 H31B 109.7 . . ? H31A C31 H31B 108.2 . . ? N4 C32 C31 109.9(2) . . ? N4 C32 H32A 109.7 . . ? C31 C32 H32A 109.7 . . ? N4 C32 H32B 109.7 . . ? C31 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? C34 C33 C38 124.2(3) . . ? C34 C33 N3 117.6(2) . . ? C38 C33 N3 118.3(2) . . ? C33 C34 C35 116.8(3) . . ? C33 C34 C39 123.5(3) . . ? C35 C34 C39 119.7(3) . . ? C36 C35 C34 120.5(3) . . ? C36 C35 H35A 119.7 . . ? C34 C35 H35A 119.7 . . ? C37 C36 C35 120.7(3) . . ? C37 C36 H36A 119.7 . . ? C35 C36 H36A 119.7 . . ? C36 C37 C38 121.4(3) . . ? C36 C37 H37A 119.3 . . ? C38 C37 H37A 119.3 . . ? C37 C38 C33 116.4(2) . . ? C37 C38 C42 120.3(2) . . ? C33 C38 C42 123.3(2) . . ? C34 C39 C41 110.9(2) . . ? C34 C39 C40 111.4(2) . . ? C41 C39 C40 110.7(2) . . ? C34 C39 H39A 107.9 . . ? C41 C39 H39A 107.9 . . ? C40 C39 H39A 107.9 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C38 C42 C43 111.9(2) . . ? C38 C42 C44 111.0(2) . . ? C43 C42 C44 110.0(2) . . ? C38 C42 H42A 107.9 . . ? C43 C42 H42A 107.9 . . ? C44 C42 H42A 107.9 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C50 123.6(3) . . ? C46 C45 N4 118.0(2) . . ? C50 C45 N4 118.1(3) . . ? C47 C46 C45 116.9(3) . . ? C47 C46 C51 120.0(3) . . ? C45 C46 C51 123.1(3) . . ? C48 C47 C46 121.2(3) . . ? C48 C47 H47A 119.4 . . ? C46 C47 H47A 119.4 . . ? C47 C48 C49 120.3(3) . . ? C47 C48 H48A 119.8 . . ? C49 C48 H48A 119.8 . . ? C48 C49 C50 121.6(3) . . ? C48 C49 H49A 119.2 . . ? C50 C49 H49A 119.2 . . ? C49 C50 C45 116.3(3) . . ? C49 C50 C54 120.9(3) . . ? C45 C50 C54 122.8(3) . . ? C46 C51 C52 112.0(3) . . ? C46 C51 C53 110.8(3) . . ? C52 C51 C53 110.9(3) . . ? C46 C51 H51A 107.6 . . ? C52 C51 H51A 107.6 . . ? C53 C51 H51A 107.6 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C51 C53 H53A 109.5 . . ? C51 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C51 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C56 C54 C50 113.1(3) . . ? C56 C54 C55 109.1(3) . . ? C50 C54 C55 110.8(3) . . ? C56 C54 H54A 107.9 . . ? C50 C54 H54A 107.9 . . ? C55 C54 H54A 107.9 . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C54 C56 H56A 109.5 . . ? C54 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C54 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? Br4 Cu1 Br3 178.71(2) . . ? Br6 Cu2 Br5 179.32(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 N2 -178.8(2) . . . . ? C2 N1 C1 N2 6.5(4) . . . . ? C5 N1 C1 Br1 3.9(3) . . . . ? C2 N1 C1 Br1 -170.92(19) . . . . ? C17 N2 C1 N1 -178.2(2) . . . . ? C4 N2 C1 N1 1.1(4) . . . . ? C17 N2 C1 Br1 -0.8(3) . . . . ? C4 N2 C1 Br1 178.49(19) . . . . ? C1 N1 C2 C3 -34.7(3) . . . . ? C5 N1 C2 C3 150.2(2) . . . . ? N1 C2 C3 C4 54.5(3) . . . . ? C1 N2 C4 C3 20.6(4) . . . . ? C17 N2 C4 C3 -160.1(2) . . . . ? C2 C3 C4 N2 -47.7(3) . . . . ? C1 N1 C5 C6 -85.8(3) . . . . ? C2 N1 C5 C6 89.2(3) . . . . ? C1 N1 C5 C10 98.3(3) . . . . ? C2 N1 C5 C10 -86.7(3) . . . . ? C10 C5 C6 C7 -0.2(4) . . . . ? N1 C5 C6 C7 -175.8(2) . . . . ? C10 C5 C6 C11 177.3(3) . . . . ? N1 C5 C6 C11 1.7(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C11 C6 C7 C8 -177.8(3) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C5 -0.6(4) . . . . ? C8 C9 C10 C14 179.4(3) . . . . ? C6 C5 C10 C9 0.6(4) . . . . ? N1 C5 C10 C9 176.3(2) . . . . ? C6 C5 C10 C14 -179.4(3) . . . . ? N1 C5 C10 C14 -3.7(4) . . . . ? C5 C6 C11 C13 129.7(3) . . . . ? C7 C6 C11 C13 -53.0(4) . . . . ? C5 C6 C11 C12 -106.4(3) . . . . ? C7 C6 C11 C12 71.0(3) . . . . ? C9 C10 C14 C15 93.7(4) . . . . ? C5 C10 C14 C15 -86.4(4) . . . . ? C9 C10 C14 C16 -30.3(4) . . . . ? C5 C10 C14 C16 149.7(3) . . . . ? C1 N2 C17 C18 -94.2(3) . . . . ? C4 N2 C17 C18 86.5(3) . . . . ? C1 N2 C17 C22 88.5(3) . . . . ? C4 N2 C17 C22 -90.8(3) . . . . ? C22 C17 C18 C19 0.6(4) . . . . ? N2 C17 C18 C19 -176.5(2) . . . . ? C22 C17 C18 C23 -178.6(3) . . . . ? N2 C17 C18 C23 4.2(4) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C23 C18 C19 C20 179.3(3) . . . . ? C18 C19 C20 C21 -0.8(4) . . . . ? C19 C20 C21 C22 0.9(4) . . . . ? C20 C21 C22 C17 -0.2(4) . . . . ? C20 C21 C22 C26 -178.9(3) . . . . ? C18 C17 C22 C21 -0.5(4) . . . . ? N2 C17 C22 C21 176.6(2) . . . . ? C18 C17 C22 C26 178.2(3) . . . . ? N2 C17 C22 C26 -4.7(4) . . . . ? C17 C18 C23 C25 -114.6(3) . . . . ? C19 C18 C23 C25 66.2(4) . . . . ? C17 C18 C23 C24 121.1(3) . . . . ? C19 C18 C23 C24 -58.1(4) . . . . ? C21 C22 C26 C27 -55.1(4) . . . . ? C17 C22 C26 C27 126.3(3) . . . . ? C21 C22 C26 C28 68.4(3) . . . . ? C17 C22 C26 C28 -110.2(3) . . . . ? C45 N4 C29 N3 169.5(3) . . . . ? C32 N4 C29 N3 -3.9(4) . . . . ? C45 N4 C29 Br2 -11.5(3) . . . . ? C32 N4 C29 Br2 175.23(19) . . . . ? C33 N3 C29 N4 170.0(2) . . . . ? C30 N3 C29 N4 -3.2(4) . . . . ? C33 N3 C29 Br2 -9.1(3) . . . . ? C30 N3 C29 Br2 177.66(19) . . . . ? C29 N3 C30 C31 -20.3(4) . . . . ? C33 N3 C30 C31 166.1(2) . . . . ? N3 C30 C31 C32 48.3(3) . . . . ? C29 N4 C32 C31 33.5(4) . . . . ? C45 N4 C32 C31 -140.2(3) . . . . ? C30 C31 C32 N4 -54.7(3) . . . . ? C29 N3 C33 C34 -83.3(3) . . . . ? C30 N3 C33 C34 90.3(3) . . . . ? C29 N3 C33 C38 98.6(3) . . . . ? C30 N3 C33 C38 -87.8(3) . . . . ? C38 C33 C34 C35 -0.1(4) . . . . ? N3 C33 C34 C35 -178.1(2) . . . . ? C38 C33 C34 C39 179.8(3) . . . . ? N3 C33 C34 C39 1.9(4) . . . . ? C33 C34 C35 C36 -0.8(4) . . . . ? C39 C34 C35 C36 179.2(3) . . . . ? C34 C35 C36 C37 0.8(4) . . . . ? C35 C36 C37 C38 0.3(4) . . . . ? C36 C37 C38 C33 -1.2(4) . . . . ? C36 C37 C38 C42 -179.8(3) . . . . ? C34 C33 C38 C37 1.1(4) . . . . ? N3 C33 C38 C37 179.0(2) . . . . ? C34 C33 C38 C42 179.7(3) . . . . ? N3 C33 C38 C42 -2.3(4) . . . . ? C33 C34 C39 C41 -114.1(3) . . . . ? C35 C34 C39 C41 65.9(3) . . . . ? C33 C34 C39 C40 122.2(3) . . . . ? C35 C34 C39 C40 -57.9(3) . . . . ? C37 C38 C42 C43 -51.7(3) . . . . ? C33 C38 C42 C43 129.7(3) . . . . ? C37 C38 C42 C44 71.5(3) . . . . ? C33 C38 C42 C44 -107.1(3) . . . . ? C29 N4 C45 C46 -81.7(3) . . . . ? C32 N4 C45 C46 91.8(3) . . . . ? C29 N4 C45 C50 103.3(3) . . . . ? C32 N4 C45 C50 -83.2(3) . . . . ? C50 C45 C46 C47 1.4(4) . . . . ? N4 C45 C46 C47 -173.3(3) . . . . ? C50 C45 C46 C51 -179.1(3) . . . . ? N4 C45 C46 C51 6.2(4) . . . . ? C45 C46 C47 C48 0.4(5) . . . . ? C51 C46 C47 C48 -179.0(3) . . . . ? C46 C47 C48 C49 -1.1(5) . . . . ? C47 C48 C49 C50 0.0(5) . . . . ? C48 C49 C50 C45 1.8(5) . . . . ? C48 C49 C50 C54 -175.7(3) . . . . ? C46 C45 C50 C49 -2.5(4) . . . . ? N4 C45 C50 C49 172.2(3) . . . . ? C46 C45 C50 C54 175.0(3) . . . . ? N4 C45 C50 C54 -10.3(4) . . . . ? C47 C46 C51 C52 -56.6(4) . . . . ? C45 C46 C51 C52 124.0(3) . . . . ? C47 C46 C51 C53 67.9(4) . . . . ? C45 C46 C51 C53 -111.6(3) . . . . ? C49 C50 C54 C56 -50.5(5) . . . . ? C45 C50 C54 C56 132.2(3) . . . . ? C49 C50 C54 C55 72.4(4) . . . . ? C45 C50 C54 C55 -104.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.741 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.094 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; # Attachment 'CUOAC2.CIF' data_CuOAc2 _database_code_depnum_ccdc_archive 'CCDC 794666' #TrackingRef 'CUOAC2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H30 Cu N2 O4' _chemical_formula_sum 'C25 H30 Cu N2 O4' _chemical_formula_weight 486.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.480(3) _cell_length_b 12.416(4) _cell_length_c 12.623(4) _cell_angle_alpha 83.440(7) _cell_angle_beta 73.973(6) _cell_angle_gamma 71.022(6) _cell_volume 1207.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2480 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.28 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 0.937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13026 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5740 _reflns_number_gt 4417 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL, v. 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^)+(0.048P)^2^+12.703P] 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 5740 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.2130 _refine_ls_wR_factor_gt 0.2021 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.86720(6) 0.74171(4) 0.73203(4) 0.01738(10) Uani 1 1 d . . . O1 O 0.8507(4) 0.8507(2) 0.6043(2) 0.0265(7) Uani 1 1 d . . . O2 O 0.7586(3) 0.7049(2) 0.6173(2) 0.0225(6) Uani 1 1 d . . . O3 O 0.8272(3) 0.6289(2) 0.8502(2) 0.0215(6) Uani 1 1 d . . . O4 O 0.6125(3) 0.7896(2) 0.8756(2) 0.0222(6) Uani 1 1 d . . . N1 N 1.2314(4) 0.7228(2) 0.6877(3) 0.0167(7) Uani 1 1 d . . . N2 N 1.1027(4) 0.7906(3) 0.8469(3) 0.0170(7) Uani 1 1 d . . . C1 C 1.0769(4) 0.7542(3) 0.7597(3) 0.0150(7) Uani 1 1 d . . . C2 C 1.3557(5) 0.7383(3) 0.7310(3) 0.0210(8) Uani 1 1 d . . . H2 H 1.4751 0.7222 0.6958 0.025 Uiso 1 1 calc R . . C3 C 1.2769(4) 0.7800(3) 0.8312(3) 0.0208(8) Uani 1 1 d . . . H3 H 1.3283 0.7987 0.8817 0.025 Uiso 1 1 calc R . . C4 C 1.2556(5) 0.6827(3) 0.5800(3) 0.0183(8) Uani 1 1 d . . . C5 C 1.2597(5) 0.5707(3) 0.5697(3) 0.0199(8) Uani 1 1 d . . . C6 C 1.2693(5) 0.5379(3) 0.4665(3) 0.0263(10) Uani 1 1 d . . . H6 H 1.2736 0.4620 0.4573 0.032 Uiso 1 1 calc R . . C7 C 1.2727(6) 0.6124(4) 0.3763(3) 0.0271(10) Uani 1 1 d . . . C8 C 1.2696(5) 0.7230(4) 0.3902(3) 0.0258(10) Uani 1 1 d . . . H8 H 1.2747 0.7741 0.3282 0.031 Uiso 1 1 calc R . . C9 C 1.2592(5) 0.7602(3) 0.4916(3) 0.0218(9) Uani 1 1 d . . . C10 C 1.2537(6) 0.4886(3) 0.6669(4) 0.0272(10) Uani 1 1 d . . . H10A H 1.2803 0.4116 0.6412 0.041 Uiso 1 1 calc R . . H10B H 1.1382 0.5109 0.7173 0.041 Uiso 1 1 calc R . . H10C H 1.3388 0.4897 0.7055 0.041 Uiso 1 1 calc R . . C11 C 1.2793(7) 0.5744(4) 0.2659(4) 0.0406(12) Uani 1 1 d . . . H11A H 1.2202 0.6395 0.2247 0.061 Uiso 1 1 calc R . . H11B H 1.2223 0.5154 0.2765 0.061 Uiso 1 1 calc R . . H11C H 1.3998 0.5434 0.2245 0.061 Uiso 1 1 calc R . . C12 C 1.2422(6) 0.8823(3) 0.5075(4) 0.0291(10) Uani 1 1 d . . . H12A H 1.2414 0.9250 0.4372 0.044 Uiso 1 1 calc R . . H12B H 1.3398 0.8850 0.5332 0.044 Uiso 1 1 calc R . . H12C H 1.1343 0.9164 0.5623 0.044 Uiso 1 1 calc R . . C13 C 0.9686(5) 0.8318(3) 0.9445(3) 0.0186(8) Uani 1 1 d . . . C14 C 0.8561(5) 0.9435(3) 0.9428(3) 0.0189(8) Uani 1 1 d . . . C15 C 0.7199(5) 0.9777(3) 1.0338(3) 0.0210(8) Uani 1 1 d . . . H15 H 0.6415 1.0525 1.0339 0.025 Uiso 1 1 calc R . . C16 C 0.6937(5) 0.9058(3) 1.1258(3) 0.0212(8) Uani 1 1 d . . . C17 C 0.8099(5) 0.7962(3) 1.1245(3) 0.0210(8) Uani 1 1 d . . . H17 H 0.7961 0.7473 1.1876 0.025 Uiso 1 1 calc R . . C18 C 0.9440(5) 0.7578(3) 1.0335(3) 0.0195(8) Uani 1 1 d . . . C19 C 0.8872(5) 1.0227(3) 0.8454(3) 0.0243(9) Uani 1 1 d . . . H19A H 0.7924 1.0945 0.8561 0.036 Uiso 1 1 calc R . . H19B H 0.8932 0.9874 0.7782 0.036 Uiso 1 1 calc R . . H19C H 0.9961 1.0378 0.8384 0.036 Uiso 1 1 calc R . . C20 C 0.5438(6) 0.9471(4) 1.2240(4) 0.0296(10) Uani 1 1 d . . . H20A H 0.5100 0.8821 1.2632 0.044 Uiso 1 1 calc R . . H20B H 0.4464 1.0004 1.1990 0.044 Uiso 1 1 calc R . . H20C H 0.5774 0.9859 1.2736 0.044 Uiso 1 1 calc R . . C21 C 1.0633(5) 0.6360(3) 1.0302(4) 0.0253(9) Uani 1 1 d . . . H21A H 1.1825 0.6365 1.0170 0.038 Uiso 1 1 calc R . . H21B H 1.0536 0.5962 0.9706 0.038 Uiso 1 1 calc R . . H21C H 1.0307 0.5967 1.1008 0.038 Uiso 1 1 calc R . . C22 C 0.7898(5) 0.7906(3) 0.5627(3) 0.0223(9) Uani 1 1 d . . . C23 C 0.7602(7) 0.8190(5) 0.4496(4) 0.0404(12) Uani 1 1 d . . . H23A H 0.6709 0.7882 0.4425 0.061 Uiso 1 1 calc R . . H23B H 0.8676 0.7854 0.3942 0.061 Uiso 1 1 calc R . . H23C H 0.7227 0.9019 0.4382 0.061 Uiso 1 1 calc R . . C24 C 0.6810(5) 0.6920(3) 0.9063(3) 0.0202(8) Uani 1 1 d . . . C25 C 0.5957(6) 0.6406(4) 1.0112(4) 0.0313(11) Uani 1 1 d . . . H25A H 0.5071 0.7013 1.0573 0.047 Uiso 1 1 calc R . . H25B H 0.6822 0.5988 1.0513 0.047 Uiso 1 1 calc R . . H25C H 0.5421 0.5882 0.9935 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01404(17) 0.01398(18) 0.0269(2) 0.00216(16) -0.00878(15) -0.00588(14) O1 0.0296(12) 0.0209(12) 0.0380(15) 0.0069(11) -0.0183(11) -0.0142(10) O2 0.0231(12) 0.0220(12) 0.0250(13) -0.0011(10) -0.0062(10) -0.0102(10) O3 0.0161(11) 0.0153(11) 0.0320(15) 0.0020(10) -0.0046(10) -0.0053(9) O4 0.0182(11) 0.0175(12) 0.0295(14) 0.0000(10) -0.0053(10) -0.0046(10) N1 0.0136(12) 0.0127(13) 0.0251(15) -0.0001(11) -0.0051(11) -0.0058(10) N2 0.0132(12) 0.0148(13) 0.0256(15) -0.0005(11) -0.0073(11) -0.0056(10) C1 0.0146(14) 0.0109(14) 0.0176(16) -0.0009(12) -0.0020(12) -0.0029(12) C2 0.0121(14) 0.0190(16) 0.034(2) 0.0001(14) -0.0083(14) -0.0055(12) C3 0.0131(14) 0.0204(17) 0.0320(19) -0.0008(14) -0.0105(14) -0.0053(13) C4 0.0194(16) 0.0144(15) 0.0172(17) 0.0004(13) -0.0010(13) -0.0036(13) C5 0.0168(15) 0.0148(15) 0.0265(19) -0.0006(14) -0.0033(14) -0.0046(13) C6 0.0324(19) 0.0182(17) 0.028(2) -0.0039(15) -0.0021(16) -0.0103(15) C7 0.0312(19) 0.029(2) 0.0189(18) -0.0055(15) -0.0020(16) -0.0086(16) C8 0.0280(18) 0.0241(18) 0.0228(19) 0.0031(15) -0.0010(15) -0.0105(15) C9 0.0203(16) 0.0184(16) 0.0242(19) 0.0011(14) -0.0020(14) -0.0062(14) C10 0.0326(19) 0.0185(17) 0.030(2) 0.0023(15) -0.0070(17) -0.0085(15) C11 0.058(3) 0.046(2) 0.026(2) -0.0057(19) -0.007(2) -0.028(2) C12 0.036(2) 0.0199(18) 0.030(2) 0.0019(16) -0.0040(17) -0.0110(16) C13 0.0201(15) 0.0170(15) 0.0211(17) -0.0042(13) -0.0066(13) -0.0065(13) C14 0.0212(15) 0.0151(15) 0.0239(18) 0.0013(13) -0.0095(13) -0.0077(13) C15 0.0244(16) 0.0136(15) 0.0258(18) -0.0048(13) -0.0071(14) -0.0048(13) C16 0.0220(16) 0.0198(16) 0.0230(18) -0.0031(14) -0.0043(14) -0.0084(14) C17 0.0264(17) 0.0176(16) 0.0205(18) 0.0045(13) -0.0068(14) -0.0097(14) C18 0.0253(16) 0.0140(15) 0.0228(18) 0.0018(13) -0.0107(14) -0.0077(13) C19 0.0261(17) 0.0162(16) 0.031(2) 0.0022(15) -0.0084(15) -0.0067(14) C20 0.031(2) 0.030(2) 0.025(2) -0.0034(16) 0.0001(17) -0.0093(17) C21 0.0281(18) 0.0152(16) 0.032(2) 0.0027(15) -0.0128(16) -0.0030(15) C22 0.0192(15) 0.0177(16) 0.031(2) 0.0035(15) -0.0103(14) -0.0053(13) C23 0.051(2) 0.045(3) 0.033(2) 0.0093(19) -0.0223(19) -0.020(2) C24 0.0177(14) 0.0188(16) 0.0282(19) -0.0028(14) -0.0070(14) -0.0094(13) C25 0.0287(19) 0.032(2) 0.031(2) 0.0030(17) -0.0009(17) -0.0131(17) _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 1.960(4) . ? Cu1 O3 1.963(3) . ? Cu1 O1 1.989(3) . ? Cu1 O2 2.077(3) . ? Cu1 O4 2.356(3) . ? Cu1 C22 2.364(4) . ? Cu1 C24 2.474(4) . ? O1 C22 1.260(5) . ? O2 C22 1.261(5) . ? O3 C24 1.289(4) . ? O4 C24 1.230(5) . ? N1 C1 1.337(4) . ? N1 C2 1.387(5) . ? N1 C4 1.439(5) . ? N2 C1 1.332(5) . ? N2 C3 1.398(5) . ? N2 C13 1.437(5) . ? C2 C3 1.331(6) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.388(5) . ? C4 C5 1.400(5) . ? C5 C6 1.383(6) . ? C5 C10 1.504(6) . ? C6 C7 1.382(6) . ? C6 H6 0.9500 . ? C7 C8 1.394(6) . ? C7 C11 1.503(6) . ? C8 C9 1.381(6) . ? C8 H8 0.9500 . ? C9 C12 1.507(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.382(5) . ? C13 C14 1.406(5) . ? C14 C15 1.376(5) . ? C14 C19 1.504(5) . ? C15 C16 1.395(5) . ? C15 H15 0.9500 . ? C16 C17 1.394(5) . ? C16 C20 1.505(5) . ? C17 C18 1.375(5) . ? C17 H17 0.9500 . ? C18 C21 1.519(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.500(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.505(6) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 O3 96.79(13) . . ? C1 Cu1 O1 98.97(13) . . ? O3 Cu1 O1 164.23(12) . . ? C1 Cu1 O2 145.81(13) . . ? O3 Cu1 O2 101.73(12) . . ? O1 Cu1 O2 64.34(12) . . ? C1 Cu1 O4 117.67(13) . . ? O3 Cu1 O4 60.55(10) . . ? O1 Cu1 O4 111.68(11) . . ? O2 Cu1 O4 96.48(11) . . ? C1 Cu1 C22 124.57(14) . . ? O3 Cu1 C22 133.75(14) . . ? O1 Cu1 C22 32.22(13) . . ? O2 Cu1 C22 32.18(13) . . ? O4 Cu1 C22 107.99(12) . . ? C1 Cu1 C24 109.63(14) . . ? O3 Cu1 C24 31.17(11) . . ? O1 Cu1 C24 139.79(12) . . ? O2 Cu1 C24 100.89(13) . . ? O4 Cu1 C24 29.39(10) . . ? C22 Cu1 C24 125.35(14) . . ? C22 O1 Cu1 90.5(2) . . ? C22 O2 Cu1 86.5(3) . . ? C24 O3 Cu1 96.8(2) . . ? C24 O4 Cu1 80.6(2) . . ? C1 N1 C2 110.4(3) . . ? C1 N1 C4 122.3(3) . . ? C2 N1 C4 127.2(3) . . ? C1 N2 C3 110.9(3) . . ? C1 N2 C13 123.7(3) . . ? C3 N2 C13 125.3(3) . . ? N2 C1 N1 105.5(3) . . ? N2 C1 Cu1 131.1(2) . . ? N1 C1 Cu1 123.4(3) . . ? C3 C2 N1 107.3(3) . . ? C3 C2 H2 126.3 . . ? N1 C2 H2 126.3 . . ? C2 C3 N2 105.8(4) . . ? C2 C3 H3 127.1 . . ? N2 C3 H3 127.1 . . ? C9 C4 C5 122.4(4) . . ? C9 C4 N1 118.2(3) . . ? C5 C4 N1 119.1(3) . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C10 120.9(4) . . ? C4 C5 C10 121.6(4) . . ? C7 C6 C5 121.8(4) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 118.7(4) . . ? C6 C7 C11 120.3(4) . . ? C8 C7 C11 121.0(4) . . ? C9 C8 C7 121.8(4) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 117.7(4) . . ? C8 C9 C12 121.3(4) . . ? C4 C9 C12 120.9(4) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 121.7(3) . . ? C18 C13 N2 119.3(3) . . ? C14 C13 N2 118.8(3) . . ? C15 C14 C13 117.7(3) . . ? C15 C14 C19 121.6(3) . . ? C13 C14 C19 120.6(3) . . ? C14 C15 C16 121.9(3) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 118.5(3) . . ? C17 C16 C20 121.5(4) . . ? C15 C16 C20 120.1(3) . . ? C18 C17 C16 121.2(4) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C13 118.9(3) . . ? C17 C18 C21 120.8(3) . . ? C13 C18 C21 120.2(3) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C22 O2 118.4(4) . . ? O1 C22 C23 120.4(4) . . ? O2 C22 C23 121.2(4) . . ? O1 C22 Cu1 57.3(2) . . ? O2 C22 Cu1 61.3(2) . . ? C23 C22 Cu1 174.1(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O4 C24 O3 122.0(4) . . ? O4 C24 C25 121.0(3) . . ? O3 C24 C25 117.0(3) . . ? O4 C24 Cu1 70.0(2) . . ? O3 C24 Cu1 51.99(18) . . ? C25 C24 Cu1 168.9(3) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C1 Cu1 O1 C22 145.8(2) . . . . ? O3 Cu1 O1 C22 -32.2(5) . . . . ? O2 Cu1 O1 C22 -2.8(2) . . . . ? O4 Cu1 O1 C22 -89.6(2) . . . . ? C24 Cu1 O1 C22 -78.7(3) . . . . ? C1 Cu1 O2 C22 -63.7(3) . . . . ? O3 Cu1 O2 C22 175.0(2) . . . . ? O1 Cu1 O2 C22 2.8(2) . . . . ? O4 Cu1 O2 C22 113.8(2) . . . . ? C24 Cu1 O2 C22 143.2(2) . . . . ? C1 Cu1 O3 C24 117.2(3) . . . . ? O1 Cu1 O3 C24 -64.9(5) . . . . ? O2 Cu1 O3 C24 -91.7(2) . . . . ? O4 Cu1 O3 C24 -0.8(2) . . . . ? C22 Cu1 O3 C24 -88.0(3) . . . . ? C1 Cu1 O4 C24 -80.9(3) . . . . ? O3 Cu1 O4 C24 0.9(2) . . . . ? O1 Cu1 O4 C24 165.6(2) . . . . ? O2 Cu1 O4 C24 100.7(2) . . . . ? C22 Cu1 O4 C24 131.5(3) . . . . ? C3 N2 C1 N1 -1.4(4) . . . . ? C13 N2 C1 N1 -179.6(3) . . . . ? C3 N2 C1 Cu1 177.7(3) . . . . ? C13 N2 C1 Cu1 -0.5(5) . . . . ? C2 N1 C1 N2 0.9(4) . . . . ? C4 N1 C1 N2 -177.3(3) . . . . ? C2 N1 C1 Cu1 -178.2(3) . . . . ? C4 N1 C1 Cu1 3.6(5) . . . . ? O3 Cu1 C1 N2 -63.5(3) . . . . ? O1 Cu1 C1 N2 117.1(3) . . . . ? O2 Cu1 C1 N2 173.9(3) . . . . ? O4 Cu1 C1 N2 -3.2(4) . . . . ? C22 Cu1 C1 N2 138.5(3) . . . . ? C24 Cu1 C1 N2 -34.2(4) . . . . ? O3 Cu1 C1 N1 115.5(3) . . . . ? O1 Cu1 C1 N1 -64.0(3) . . . . ? O2 Cu1 C1 N1 -7.2(4) . . . . ? O4 Cu1 C1 N1 175.7(3) . . . . ? C22 Cu1 C1 N1 -42.6(4) . . . . ? C24 Cu1 C1 N1 144.7(3) . . . . ? C1 N1 C2 C3 -0.1(4) . . . . ? C4 N1 C2 C3 178.0(3) . . . . ? N1 C2 C3 N2 -0.7(4) . . . . ? C1 N2 C3 C2 1.3(4) . . . . ? C13 N2 C3 C2 179.5(3) . . . . ? C1 N1 C4 C9 96.5(4) . . . . ? C2 N1 C4 C9 -81.4(5) . . . . ? C1 N1 C4 C5 -78.1(4) . . . . ? C2 N1 C4 C5 104.0(4) . . . . ? C9 C4 C5 C6 0.6(6) . . . . ? N1 C4 C5 C6 174.9(3) . . . . ? C9 C4 C5 C10 -179.3(4) . . . . ? N1 C4 C5 C10 -5.0(5) . . . . ? C4 C5 C6 C7 -0.7(6) . . . . ? C10 C5 C6 C7 179.2(4) . . . . ? C5 C6 C7 C8 1.2(6) . . . . ? C5 C6 C7 C11 -178.7(4) . . . . ? C6 C7 C8 C9 -1.5(6) . . . . ? C11 C7 C8 C9 178.4(4) . . . . ? C7 C8 C9 C4 1.4(6) . . . . ? C7 C8 C9 C12 -175.2(4) . . . . ? C5 C4 C9 C8 -0.9(6) . . . . ? N1 C4 C9 C8 -175.3(3) . . . . ? C5 C4 C9 C12 175.7(4) . . . . ? N1 C4 C9 C12 1.3(6) . . . . ? C1 N2 C13 C18 95.5(5) . . . . ? C3 N2 C13 C18 -82.5(5) . . . . ? C1 N2 C13 C14 -78.9(5) . . . . ? C3 N2 C13 C14 103.2(4) . . . . ? C18 C13 C14 C15 0.4(6) . . . . ? N2 C13 C14 C15 174.6(4) . . . . ? C18 C13 C14 C19 179.2(4) . . . . ? N2 C13 C14 C19 -6.6(6) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C19 C14 C15 C16 -177.9(4) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C14 C15 C16 C20 179.5(4) . . . . ? C15 C16 C17 C18 -2.3(6) . . . . ? C20 C16 C17 C18 178.3(4) . . . . ? C16 C17 C18 C13 3.5(6) . . . . ? C16 C17 C18 C21 -176.2(4) . . . . ? C14 C13 C18 C17 -2.6(6) . . . . ? N2 C13 C18 C17 -176.8(4) . . . . ? C14 C13 C18 C21 177.1(4) . . . . ? N2 C13 C18 C21 3.0(6) . . . . ? Cu1 O1 C22 O2 4.7(3) . . . . ? Cu1 O1 C22 C23 -173.6(3) . . . . ? Cu1 O2 C22 O1 -4.5(3) . . . . ? Cu1 O2 C22 C23 173.8(4) . . . . ? C1 Cu1 C22 O1 -42.4(3) . . . . ? O3 Cu1 C22 O1 168.44(19) . . . . ? O2 Cu1 C22 O1 175.3(3) . . . . ? O4 Cu1 C22 O1 102.3(2) . . . . ? C24 Cu1 C22 O1 129.1(2) . . . . ? C1 Cu1 C22 O2 142.3(2) . . . . ? O3 Cu1 C22 O2 -6.8(3) . . . . ? O1 Cu1 C22 O2 -175.3(3) . . . . ? O4 Cu1 C22 O2 -73.0(2) . . . . ? C24 Cu1 C22 O2 -46.2(3) . . . . ? Cu1 O4 C24 O3 -1.4(4) . . . . ? Cu1 O4 C24 C25 179.3(4) . . . . ? Cu1 O3 C24 O4 1.6(4) . . . . ? Cu1 O3 C24 C25 -179.1(3) . . . . ? C1 Cu1 C24 O4 111.8(2) . . . . ? O3 Cu1 C24 O4 -178.5(4) . . . . ? O1 Cu1 C24 O4 -20.9(3) . . . . ? O2 Cu1 C24 O4 -83.8(2) . . . . ? C22 Cu1 C24 O4 -60.8(3) . . . . ? C1 Cu1 C24 O3 -69.7(3) . . . . ? O1 Cu1 C24 O3 157.6(2) . . . . ? O2 Cu1 C24 O3 94.7(2) . . . . ? O4 Cu1 C24 O3 178.5(4) . . . . ? C22 Cu1 C24 O3 117.7(2) . . . . ? C1 Cu1 C24 C25 -65.3(17) . . . . ? O3 Cu1 C24 C25 4.4(16) . . . . ? O1 Cu1 C24 C25 162.0(16) . . . . ? O2 Cu1 C24 C25 99.1(17) . . . . ? O4 Cu1 C24 C25 -177.1(18) . . . . ? C22 Cu1 C24 C25 122.1(17) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.716 _refine_diff_density_min -1.148 _refine_diff_density_rms 0.173 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; # Attachment 'KE125.CIF' data_KE-125 _database_code_depnum_ccdc_archive 'CCDC 794667' #TrackingRef 'KE125.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H34 Cu N2 O4' _chemical_formula_sum 'C26 H34 Cu N2 O4' _chemical_formula_weight 502.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 23.7798(11) _cell_length_b 8.8383(4) _cell_length_c 16.8227(14) _cell_angle_alpha 90.00 _cell_angle_beta 134.8860(10) _cell_angle_gamma 90.00 _cell_volume 2505.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3463 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.72 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11686 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4837 _reflns_number_gt 4104 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL, v. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL, v. 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^)+(0.073P)^2^+47P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.26(3) _refine_ls_number_reflns 4837 _refine_ls_number_parameters 156 _refine_ls_number_restraints 101 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.1994 _refine_ls_wR_factor_gt 0.1762 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.060 _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 0.07445(11) 0.12809(7) 0.23854(17) 0.0192(2) Uani 1 1 d D . . O1 O -0.04013(19) 0.0918(6) 0.1261(4) 0.0218(5) Uani 1 1 d D . . O2 O 0.0240(2) -0.0479(6) 0.1054(4) 0.0218(5) Uani 1 1 d D . . O3 O 0.1890(2) 0.0877(6) 0.3521(4) 0.0218(5) Uani 1 1 d D . . O4 O 0.1224(3) -0.0493(6) 0.3696(4) 0.0218(5) Uani 1 1 d D . . N1 N 0.04241(13) 0.4356(3) 0.15143(14) 0.0277(7) Uani 1 1 d D . . N2 N 0.08870(12) 0.4219(3) 0.32571(13) 0.0277(7) Uani 1 1 d D . . C1 C 0.06766(5) 0.3516(3) 0.23785(13) 0.0277(7) Uani 1 1 d D . . C2 C 0.03638(18) 0.6020(3) 0.1473(2) 0.0277(7) Uani 1 1 d D . . H2A H -0.0069 0.6363 0.0686 0.033 Uiso 1 1 calc R . . H2B H 0.0867 0.6479 0.1789 0.033 Uiso 1 1 calc R . . C3 C 0.0192(3) 0.6508(5) 0.2160(3) 0.0277(7) Uani 1 1 d D . . H3A H 0.0175 0.7625 0.2182 0.033 Uiso 1 1 calc R . . H3B H -0.0326 0.6101 0.1819 0.033 Uiso 1 1 calc R . . C4 C 0.08620(17) 0.5877(3) 0.3349(2) 0.0277(7) Uani 1 1 d D . . H4A H 0.1376 0.6334 0.3706 0.033 Uiso 1 1 calc R . . H4B H 0.0761 0.6116 0.3814 0.033 Uiso 1 1 calc R . . C5 C 0.01698(16) 0.3605(3) 0.05431(17) 0.0258(7) Uani 1 1 d D . . C6 C 0.07242(18) 0.3154(4) 0.0536(3) 0.0258(7) Uani 1 1 d D . . C7 C 0.0461(2) 0.2435(5) -0.0411(3) 0.0258(7) Uani 1 1 d D . . H7A H 0.0835 0.2120 -0.0425 0.031 Uiso 1 1 calc R . . C8 C -0.0342(2) 0.2167(4) -0.1338(3) 0.0258(7) Uani 1 1 d D . . C9 C -0.0886(2) 0.2632(5) -0.1308(3) 0.0258(7) Uani 1 1 d D . . H9A H -0.1436 0.2453 -0.1939 0.031 Uiso 1 1 calc R . . C10 C -0.06388(16) 0.3352(4) -0.0374(2) 0.0258(7) Uani 1 1 d D . . C11 C 0.16046(19) 0.3423(7) 0.1527(4) 0.0341(12) Uani 1 1 d D . . H11A H 0.1884 0.3214 0.1306 0.051 Uiso 1 1 calc R . . H11B H 0.1806 0.2751 0.2145 0.051 Uiso 1 1 calc R . . H11C H 0.1694 0.4478 0.1771 0.051 Uiso 1 1 calc R . . C12 C -0.0619(3) 0.1382(6) -0.2362(3) 0.0341(12) Uani 1 1 d D . . H12A H -0.0173 0.0840 -0.2159 0.051 Uiso 1 1 calc R . . H12B H -0.0823 0.2135 -0.2941 0.051 Uiso 1 1 calc R . . H12C H -0.1041 0.0661 -0.2651 0.051 Uiso 1 1 calc R . . C13 C -0.1236(3) 0.3851(7) -0.0353(5) 0.0341(12) Uani 1 1 d D . . H13A H -0.1769 0.3540 -0.1050 0.051 Uiso 1 1 calc R . . H13B H -0.1218 0.4955 -0.0281 0.051 Uiso 1 1 calc R . . H13C H -0.1108 0.3382 0.0287 0.051 Uiso 1 1 calc R . . C14 C 0.12855(15) 0.3381(3) 0.42762(15) 0.0253(7) Uani 1 1 d D . . C15 C 0.08275(18) 0.2685(4) 0.4402(2) 0.0253(7) Uani 1 1 d D . . C16 C 0.1207(2) 0.1880(4) 0.5378(3) 0.0253(7) Uani 1 1 d D . . H16A H 0.0900 0.1401 0.5473 0.030 Uiso 1 1 calc R . . C17 C 0.2029(2) 0.1764(4) 0.6219(3) 0.0253(7) Uani 1 1 d D . . C18 C 0.2471(2) 0.2469(5) 0.6071(2) 0.0253(7) Uani 1 1 d D . . H18A H 0.3034 0.2395 0.6642 0.030 Uiso 1 1 calc R . . C19 C 0.21067(15) 0.3283(4) 0.5102(2) 0.0253(7) Uani 1 1 d D . . C20 C -0.00687(19) 0.2784(7) 0.3508(4) 0.0378(12) Uani 1 1 d D . . H20A H -0.0270 0.2566 0.3842 0.057 Uiso 1 1 calc R . . H20B H -0.0285 0.2045 0.2916 0.057 Uiso 1 1 calc R . . H20C H -0.0232 0.3804 0.3186 0.057 Uiso 1 1 calc R . . C21 C 0.2437(4) 0.0882(6) 0.7280(3) 0.0378(12) Uani 1 1 d D . . H21A H 0.2730 0.1581 0.7916 0.057 Uiso 1 1 calc R . . H21B H 0.2806 0.0152 0.7413 0.057 Uiso 1 1 calc R . . H21C H 0.2038 0.0342 0.7197 0.057 Uiso 1 1 calc R . . C22 C 0.2616(3) 0.4029(7) 0.4982(5) 0.0378(12) Uani 1 1 d D . . H22A H 0.2417 0.3759 0.4255 0.057 Uiso 1 1 calc R . . H22B H 0.3165 0.3683 0.5586 0.057 Uiso 1 1 calc R . . H22C H 0.2595 0.5130 0.5028 0.057 Uiso 1 1 calc R . . C23 C -0.0382(2) -0.0100(5) 0.0725(3) 0.0235(7) Uani 1 1 d D . . C24 C -0.1146(3) -0.0794(9) -0.0311(5) 0.0235(7) Uani 1 1 d D . . H24A H -0.1038 -0.1531 -0.0624 0.035 Uiso 1 1 calc R . . H24B H -0.1497 0.0000 -0.0866 0.035 Uiso 1 1 calc R . . H24C H -0.1404 -0.1304 -0.0120 0.035 Uiso 1 1 calc R . . C25 C 0.1852(2) -0.0148(5) 0.4034(3) 0.0235(7) Uani 1 1 d D . . C26 C 0.2602(3) -0.0903(9) 0.5054(5) 0.0235(7) Uani 1 1 d D . . H26A H 0.2561 -0.1137 0.5581 0.035 Uiso 1 1 calc R . . H26B H 0.3053 -0.0224 0.5415 0.035 Uiso 1 1 calc R . . H26C H 0.2681 -0.1841 0.4833 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0168(4) 0.0111(3) 0.0307(4) 0.0013(5) 0.0170(3) 0.0002(5) O1 0.0203(10) 0.0182(10) 0.0287(11) 0.0032(19) 0.0180(9) 0.0055(18) O2 0.0203(10) 0.0182(10) 0.0287(11) 0.0032(19) 0.0180(9) 0.0055(18) O3 0.0203(10) 0.0182(10) 0.0287(11) 0.0032(19) 0.0180(9) 0.0055(18) O4 0.0203(10) 0.0182(10) 0.0287(11) 0.0032(19) 0.0180(9) 0.0055(18) N1 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) N2 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) C1 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) C2 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) C3 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) C4 0.0282(16) 0.0183(14) 0.0192(12) 0.0016(14) 0.0106(12) 0.0034(13) C5 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C6 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C7 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C8 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C9 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C10 0.0214(17) 0.0337(18) 0.0214(17) 0.0022(14) 0.0148(15) 0.0037(14) C11 0.023(2) 0.049(3) 0.034(3) 0.002(2) 0.022(2) 0.005(2) C12 0.023(2) 0.049(3) 0.034(3) 0.002(2) 0.022(2) 0.005(2) C13 0.023(2) 0.049(3) 0.034(3) 0.002(2) 0.022(2) 0.005(2) C14 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C15 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C16 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C17 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C18 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C19 0.0307(18) 0.0303(17) 0.0208(16) -0.0056(13) 0.0202(16) -0.0032(14) C20 0.035(3) 0.048(3) 0.035(3) -0.002(2) 0.026(3) 0.000(2) C21 0.035(3) 0.048(3) 0.035(3) -0.002(2) 0.026(3) 0.000(2) C22 0.035(3) 0.048(3) 0.035(3) -0.002(2) 0.026(3) 0.000(2) C23 0.0231(15) 0.0212(15) 0.0248(15) 0.003(3) 0.0164(14) 0.008(3) C24 0.0231(15) 0.0212(15) 0.0248(15) 0.003(3) 0.0164(14) 0.008(3) C25 0.0231(15) 0.0212(15) 0.0248(15) 0.003(3) 0.0164(14) 0.008(3) C26 0.0231(15) 0.0212(15) 0.0248(15) 0.003(3) 0.0164(14) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.957(3) . ? Cu1 O3 1.962(3) . ? Cu1 C1 1.981(3) . ? Cu1 O4 2.252(3) . ? Cu1 O2 2.254(3) . ? O1 C23 1.297(7) . ? O2 C23 1.205(9) . ? O3 C25 1.298(7) . ? O4 C25 1.203(10) . ? N1 C1 1.339(5) . ? N1 C5 1.443(5) . ? N1 C2 1.475(4) . ? N2 C1 1.333(4) . ? N2 C14 1.447(5) . ? N2 C4 1.478(4) . ? C2 C3 1.535(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.385(7) . ? C5 C10 1.393(5) . ? C6 C7 1.388(6) . ? C6 C11 1.514(7) . ? C7 C8 1.390(6) . ? C7 H7A 0.9500 . ? C8 C9 1.392(8) . ? C8 C12 1.510(6) . ? C9 C10 1.384(5) . ? C9 H9A 0.9500 . ? C10 C13 1.511(10) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 C19 1.386(5) . ? C14 C15 1.391(6) . ? C15 C16 1.387(5) . ? C15 C20 1.512(7) . ? C16 C17 1.389(7) . ? C16 H16A 0.9500 . ? C17 C18 1.387(8) . ? C17 C21 1.513(6) . ? C18 C19 1.390(5) . ? C18 H18A 0.9500 . ? C19 C22 1.512(10) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C24 1.498(8) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.500(8) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 O1 Cu1 O3 160.1(2) . . ? O1 Cu1 C1 96.1(2) . . ? O3 Cu1 C1 103.8(2) . . ? O1 Cu1 O4 103.3(2) . . ? O3 Cu1 O4 61.6(3) . . ? C1 Cu1 O4 133.0(2) . . ? O1 Cu1 O2 61.6(2) . . ? O3 Cu1 O2 104.0(2) . . ? C1 Cu1 O2 134.3(2) . . ? O4 Cu1 O2 92.2(2) . . ? C23 O1 Cu1 94.4(4) . . ? C23 O2 Cu1 83.4(4) . . ? C25 O3 Cu1 94.3(4) . . ? C25 O4 Cu1 83.6(4) . . ? C1 N1 C5 118.9(2) . . ? C1 N1 C2 124.0(2) . . ? C5 N1 C2 117.1(2) . . ? C1 N2 C14 119.6(2) . . ? C1 N2 C4 124.5(2) . . ? C14 N2 C4 115.1(2) . . ? N2 C1 N1 118.3(2) . . ? N2 C1 Cu1 119.6(2) . . ? N1 C1 Cu1 122.1(2) . . ? N1 C2 C3 108.2(2) . . ? N1 C2 H2A 110.1 . . ? C3 C2 H2A 110.1 . . ? N1 C2 H2B 110.1 . . ? C3 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? C4 C3 C2 107.2(2) . . ? C4 C3 H3A 110.3 . . ? C2 C3 H3A 110.3 . . ? C4 C3 H3B 110.3 . . ? C2 C3 H3B 110.3 . . ? H3A C3 H3B 108.5 . . ? N2 C4 C3 107.8(2) . . ? N2 C4 H4A 110.1 . . ? C3 C4 H4A 110.1 . . ? N2 C4 H4B 110.1 . . ? C3 C4 H4B 110.1 . . ? H4A C4 H4B 108.5 . . ? C6 C5 C10 121.5(2) . . ? C6 C5 N1 120.1(2) . . ? C10 C5 N1 118.5(2) . . ? C5 C6 C7 118.7(4) . . ? C5 C6 C11 122.0(2) . . ? C7 C6 C11 119.3(5) . . ? C6 C7 C8 121.0(5) . . ? C6 C7 H7A 119.4 . . ? C8 C7 H7A 119.4 . . ? C7 C8 C9 119.0(4) . . ? C7 C8 C12 120.4(5) . . ? C9 C8 C12 120.6(2) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 C5 118.8(4) . . ? C9 C10 C13 120.5(2) . . ? C5 C10 C13 120.8(2) . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C19 C14 C15 121.35(18) . . ? C19 C14 N2 120.1(2) . . ? C15 C14 N2 118.6(2) . . ? C16 C15 C14 118.8(4) . . ? C16 C15 C20 119.3(5) . . ? C14 C15 C20 121.9(4) . . ? C15 C16 C17 121.0(5) . . ? C15 C16 H16A 119.4 . . ? C17 C16 H16A 119.4 . . ? C18 C17 C16 118.90(19) . . ? C18 C17 C21 120.4(5) . . ? C16 C17 C21 120.6(6) . . ? C17 C18 C19 121.2(2) . . ? C17 C18 H18A 119.4 . . ? C19 C18 H18A 119.4 . . ? C14 C19 C18 118.6(2) . . ? C14 C19 C22 122.2(2) . . ? C18 C19 C22 119.1(2) . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O2 C23 O1 120.5(5) . . ? O2 C23 C24 120.6(5) . . ? O1 C23 C24 118.9(6) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C25 O3 120.6(5) . . ? O4 C25 C26 120.3(3) . . ? O3 C25 C26 119.1(6) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O3 Cu1 O1 C23 -48.1(10) . . . . ? C1 Cu1 O1 C23 136.7(3) . . . . ? O4 Cu1 O1 C23 -86.4(3) . . . . ? O2 Cu1 O1 C23 -1.07(18) . . . . ? O1 Cu1 O2 C23 1.2(2) . . . . ? O3 Cu1 O2 C23 166.3(3) . . . . ? C1 Cu1 O2 C23 -67.8(3) . . . . ? O4 Cu1 O2 C23 105.0(3) . . . . ? O1 Cu1 O3 C25 -43.8(10) . . . . ? C1 Cu1 O3 C25 131.3(3) . . . . ? O4 Cu1 O3 C25 -0.48(18) . . . . ? O2 Cu1 O3 C25 -85.4(3) . . . . ? O1 Cu1 O4 C25 166.6(3) . . . . ? O3 Cu1 O4 C25 0.52(19) . . . . ? C1 Cu1 O4 C25 -81.8(3) . . . . ? O2 Cu1 O4 C25 105.2(3) . . . . ? C14 N2 C1 N1 -169.6(2) . . . . ? C14 N2 C1 Cu1 10.4(2) . . . . ? C5 N1 C1 N2 -178.0(2) . . . . ? C5 N1 C1 Cu1 2.0(2) . . . . ? O1 Cu1 C1 N2 108.4(2) . . . . ? O3 Cu1 C1 N2 -69.94(19) . . . . ? O4 Cu1 C1 N2 -6.2(4) . . . . ? O2 Cu1 C1 N2 164.1(2) . . . . ? C23 Cu1 C1 N2 132.91(16) . . . . ? C25 Cu1 C1 N2 -41.57(17) . . . . ? O1 Cu1 C1 N1 -71.6(2) . . . . ? O3 Cu1 C1 N1 110.06(19) . . . . ? O4 Cu1 C1 N1 173.9(4) . . . . ? O2 Cu1 C1 N1 -15.9(2) . . . . ? C23 Cu1 C1 N1 -47.08(16) . . . . ? C25 Cu1 C1 N1 138.44(17) . . . . ? C1 N1 C2 C3 -29.9(5) . . . . ? C5 N1 C2 C3 148.1(3) . . . . ? N1 C2 C3 C4 57.0(4) . . . . ? C1 N2 C4 C3 29.8(6) . . . . ? C14 N2 C4 C3 -160.1(3) . . . . ? C2 C3 C4 N2 -56.7(4) . . . . ? C1 N1 C5 C6 -83.0(2) . . . . ? C2 N1 C5 C6 98.9(4) . . . . ? C1 N1 C5 C10 97.0(2) . . . . ? C2 N1 C5 C10 -81.1(4) . . . . ? C1 N2 C14 C19 89.7(2) . . . . ? C4 N2 C14 C19 -80.9(4) . . . . ? C1 N2 C14 C15 -90.4(2) . . . . ? C4 N2 C14 C15 99.1(4) . . . . ? Cu1 O2 C23 O1 -1.8(3) . . . . ? Cu1 O2 C23 C24 178.2(3) . . . . ? Cu1 O1 C23 O2 2.1(4) . . . . ? Cu1 O1 C23 C24 -177.9(4) . . . . ? Cu1 O4 C25 O3 -0.8(3) . . . . ? Cu1 O4 C25 C26 179.2(3) . . . . ? Cu1 O3 C25 O4 0.9(3) . . . . ? Cu1 O3 C25 C26 -179.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.842 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.094 _publ_section_references ; Bruker (2001). SAINTPlus, v. 6.2. Data Reduction and Correction Program, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package, v. 1.27. Bruker Molecular Analysis Research Tool, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS, v. 2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; # Attachment 'kev.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 794668' #TrackingRef 'kev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 Br N2, 2(C H Cl3), Br' _chemical_formula_sum 'C30 H42 Br2 Cl6 N2' _chemical_formula_weight 803.16 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' 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 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.9457(12) _cell_length_b 21.357(2) _cell_length_c 15.7609(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.597(2) _cell_angle_gamma 90.00 _cell_volume 3666.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3586 _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 2.67 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.532 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 36710 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.1633 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.00 _reflns_number_total 8795 _reflns_number_gt 4225 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SAINTPlus (Bruker, 1998a)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0579P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8795 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 0.871 _refine_ls_restrained_S_all 0.871 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.29906(5) 0.21232(2) 1.07874(3) 0.02034(14) Uani 1 1 d . . . Br2 Br 0.44702(6) 0.16494(3) 1.24681(4) 0.03636(18) Uani 1 1 d . . . N1 N 0.2390(4) 0.20953(19) 0.9045(3) 0.0152(9) Uani 1 1 d . . . N2 N 0.2272(4) 0.30807(19) 0.9656(3) 0.0151(9) Uani 1 1 d . . . C1 C 0.2471(4) 0.2468(2) 0.9712(3) 0.0157(11) Uani 1 1 d . . . C2 C 0.2127(5) 0.2345(2) 0.8170(3) 0.0207(12) Uani 1 1 d . . . H2A H 0.1685 0.2025 0.7803 0.025 Uiso 1 1 calc R . . H2B H 0.2908 0.2441 0.7929 0.025 Uiso 1 1 calc R . . C3 C 0.1360(5) 0.2928(2) 0.8181(3) 0.0233(12) Uani 1 1 d . . . H3A H 0.0530 0.2822 0.8335 0.028 Uiso 1 1 calc R . . H3B H 0.1276 0.3123 0.7608 0.028 Uiso 1 1 calc R . . C4 C 0.1978(5) 0.3384(2) 0.8830(3) 0.0189(12) Uani 1 1 d . . . H4A H 0.2741 0.3546 0.8621 0.023 Uiso 1 1 calc R . . H4B H 0.1425 0.3744 0.8898 0.023 Uiso 1 1 calc R . . C5 C 0.2563(5) 0.1426(2) 0.9101(3) 0.0177(12) Uani 1 1 d . . . C6 C 0.1501(5) 0.1054(2) 0.9084(3) 0.0193(12) Uani 1 1 d . . . C7 C 0.1655(5) 0.0413(3) 0.9036(3) 0.0264(13) Uani 1 1 d . . . H7A H 0.0956 0.0147 0.9017 0.032 Uiso 1 1 calc R . . C8 C 0.2791(6) 0.0154(3) 0.9015(3) 0.0264(14) Uani 1 1 d . . . H8A H 0.2869 -0.0286 0.8960 0.032 Uiso 1 1 calc R . . C9 C 0.3834(5) 0.0527(3) 0.9072(3) 0.0252(13) Uani 1 1 d . . . H9A H 0.4620 0.0335 0.9094 0.030 Uiso 1 1 calc R . . C10 C 0.3750(5) 0.1177(3) 0.9098(3) 0.0217(12) Uani 1 1 d . . . C11 C 0.0232(5) 0.1342(3) 0.9134(4) 0.0257(13) Uani 1 1 d . . . H11A H 0.0342 0.1806 0.9187 0.031 Uiso 1 1 calc R . . C12 C -0.0609(5) 0.1221(3) 0.8338(4) 0.0336(15) Uani 1 1 d . . . H12A H -0.0234 0.1384 0.7843 0.050 Uiso 1 1 calc R . . H12B H -0.1397 0.1430 0.8381 0.050 Uiso 1 1 calc R . . H12C H -0.0742 0.0769 0.8270 0.050 Uiso 1 1 calc R . . C13 C -0.0346(6) 0.1116(3) 0.9930(4) 0.0448(18) Uani 1 1 d . . . H13A H -0.1088 0.1360 0.9998 0.067 Uiso 1 1 calc R . . H13B H 0.0242 0.1172 1.0434 0.067 Uiso 1 1 calc R . . H13C H -0.0561 0.0672 0.9865 0.067 Uiso 1 1 calc R . . C14 C 0.4879(5) 0.1583(3) 0.9118(4) 0.0264(13) Uani 1 1 d . . . H14A H 0.4617 0.2025 0.9204 0.032 Uiso 1 1 calc R . . C15 C 0.5452(5) 0.1556(3) 0.8269(4) 0.0330(15) Uani 1 1 d . . . H15A H 0.4865 0.1718 0.7812 0.050 Uiso 1 1 calc R . . H15B H 0.5659 0.1121 0.8143 0.050 Uiso 1 1 calc R . . H15C H 0.6199 0.1812 0.8308 0.050 Uiso 1 1 calc R . . C16 C 0.5819(6) 0.1417(3) 0.9850(4) 0.0380(16) Uani 1 1 d . . . H16A H 0.5429 0.1418 1.0384 0.057 Uiso 1 1 calc R . . H16B H 0.6485 0.1726 0.9886 0.057 Uiso 1 1 calc R . . H16C H 0.6154 0.1000 0.9756 0.057 Uiso 1 1 calc R . . C17 C 0.2480(5) 0.3497(2) 1.0386(3) 0.0197(12) Uani 1 1 d . . . C18 C 0.1455(5) 0.3705(2) 1.0777(3) 0.0199(12) Uani 1 1 d . . . C19 C 0.1669(5) 0.4099(3) 1.1480(4) 0.0279(14) Uani 1 1 d . . . H19A H 0.1000 0.4236 1.1773 0.033 Uiso 1 1 calc R . . C20 C 0.2849(5) 0.4291(3) 1.1755(4) 0.0298(14) Uani 1 1 d . . . H20A H 0.2982 0.4560 1.2235 0.036 Uiso 1 1 calc R . . C21 C 0.3829(5) 0.4098(3) 1.1339(4) 0.0305(14) Uani 1 1 d . . . H21A H 0.4628 0.4240 1.1538 0.037 Uiso 1 1 calc R . . C22 C 0.3689(5) 0.3700(3) 1.0633(4) 0.0252(13) Uani 1 1 d . . . C23 C 0.0151(5) 0.3499(3) 1.0463(4) 0.0234(13) Uani 1 1 d . . . H23A H 0.0141 0.3395 0.9844 0.028 Uiso 1 1 calc R . . C24 C -0.0207(5) 0.2906(3) 1.0922(4) 0.0380(16) Uani 1 1 d . . . H24A H -0.0966 0.2734 1.0631 0.057 Uiso 1 1 calc R . . H24B H -0.0337 0.3008 1.1512 0.057 Uiso 1 1 calc R . . H24C H 0.0451 0.2596 1.0916 0.057 Uiso 1 1 calc R . . C25 C -0.0780(5) 0.4009(3) 1.0543(4) 0.0422(17) Uani 1 1 d . . . H25A H -0.1584 0.3870 1.0284 0.063 Uiso 1 1 calc R . . H25B H -0.0531 0.4386 1.0250 0.063 Uiso 1 1 calc R . . H25C H -0.0830 0.4104 1.1147 0.063 Uiso 1 1 calc R . . C26 C 0.4780(5) 0.3510(3) 1.0179(4) 0.0250(13) Uani 1 1 d . . . H26A H 0.4493 0.3202 0.9725 0.030 Uiso 1 1 calc R . . C27 C 0.5317(5) 0.4076(3) 0.9747(4) 0.0340(15) Uani 1 1 d . . . H27A H 0.4687 0.4259 0.9336 0.051 Uiso 1 1 calc R . . H27B H 0.6017 0.3941 0.9450 0.051 Uiso 1 1 calc R . . H27C H 0.5589 0.4389 1.0179 0.051 Uiso 1 1 calc R . . C28 C 0.5765(5) 0.3193(3) 1.0785(4) 0.0357(16) Uani 1 1 d . . . H28A H 0.5395 0.2851 1.1087 0.054 Uiso 1 1 calc R . . H28B H 0.6125 0.3500 1.1199 0.054 Uiso 1 1 calc R . . H28C H 0.6407 0.3024 1.0458 0.054 Uiso 1 1 calc R . . C2S C 0.7573(6) 0.1581(3) 0.2877(4) 0.0429(18) Uani 1 1 d . . . H1SA H 0.6662 0.1538 0.2769 0.051 Uiso 1 1 calc R . . C1S C 0.7503(5) 0.5390(3) 0.2802(4) 0.0289(14) Uani 1 1 d . . . H2SA H 0.7025 0.5781 0.2655 0.035 Uiso 1 1 calc R . . Cl1 Cl 0.90794(13) 0.55576(7) 0.27486(10) 0.0367(4) Uani 1 1 d . . . Cl2 Cl 0.70225(15) 0.48195(8) 0.20550(10) 0.0429(4) Uani 1 1 d . . . Cl3 Cl 0.72509(15) 0.51724(8) 0.38459(10) 0.0414(4) Uani 1 1 d . . . Cl4 Cl 0.8158(2) 0.18104(14) 0.19430(14) 0.0937(9) Uani 1 1 d . . . Cl5 Cl 0.82019(19) 0.08553(9) 0.32179(13) 0.0607(5) Uani 1 1 d . . . Cl6 Cl 0.79237(15) 0.21297(8) 0.37052(13) 0.0527(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0245(3) 0.0204(3) 0.0157(3) 0.0016(2) -0.0002(2) 0.0009(2) Br2 0.0281(3) 0.0467(4) 0.0337(4) 0.0065(3) 0.0001(3) -0.0008(3) N1 0.018(2) 0.012(2) 0.017(2) 0.0001(19) 0.0029(17) 0.0026(18) N2 0.015(2) 0.019(2) 0.012(2) -0.0001(18) 0.0012(18) 0.0004(18) C1 0.012(3) 0.019(3) 0.017(3) -0.003(2) 0.001(2) 0.003(2) C2 0.029(3) 0.019(3) 0.013(3) 0.000(2) -0.001(2) -0.002(2) C3 0.024(3) 0.028(3) 0.017(3) 0.001(2) -0.003(2) -0.002(3) C4 0.026(3) 0.011(3) 0.020(3) 0.001(2) 0.003(2) 0.001(2) C5 0.030(3) 0.010(3) 0.013(3) 0.000(2) -0.001(2) 0.002(2) C6 0.024(3) 0.021(3) 0.012(3) 0.001(2) 0.001(2) -0.003(2) C7 0.039(4) 0.023(3) 0.017(3) 0.004(2) 0.004(3) -0.010(3) C8 0.054(4) 0.010(3) 0.014(3) 0.002(2) -0.003(3) 0.007(3) C9 0.035(3) 0.019(3) 0.022(3) 0.003(2) 0.004(3) 0.010(3) C10 0.027(3) 0.023(3) 0.014(3) 0.000(2) -0.003(2) 0.002(3) C11 0.022(3) 0.025(3) 0.030(3) 0.002(3) 0.002(3) -0.006(2) C12 0.026(3) 0.036(4) 0.037(4) -0.003(3) -0.003(3) -0.002(3) C13 0.031(4) 0.073(5) 0.030(4) 0.019(3) -0.001(3) -0.003(3) C14 0.020(3) 0.024(3) 0.035(4) -0.002(3) -0.002(3) 0.000(2) C15 0.027(3) 0.029(4) 0.043(4) -0.008(3) 0.003(3) 0.001(3) C16 0.029(3) 0.040(4) 0.043(4) -0.012(3) -0.006(3) 0.008(3) C17 0.024(3) 0.017(3) 0.018(3) -0.007(2) 0.004(2) -0.004(2) C18 0.018(3) 0.022(3) 0.019(3) -0.001(2) 0.000(2) 0.000(2) C19 0.029(3) 0.032(4) 0.023(3) -0.003(3) 0.009(3) 0.004(3) C20 0.033(4) 0.036(4) 0.019(3) -0.013(3) -0.008(3) 0.002(3) C21 0.024(3) 0.035(4) 0.030(3) -0.012(3) -0.011(3) -0.002(3) C22 0.028(3) 0.024(3) 0.023(3) 0.003(2) 0.003(3) 0.001(3) C23 0.022(3) 0.030(3) 0.019(3) -0.003(2) 0.005(2) 0.000(2) C24 0.029(3) 0.039(4) 0.046(4) 0.007(3) 0.003(3) -0.004(3) C25 0.024(3) 0.040(4) 0.060(5) -0.007(3) -0.008(3) 0.008(3) C26 0.019(3) 0.031(3) 0.025(3) -0.006(3) 0.003(2) -0.001(2) C27 0.023(3) 0.044(4) 0.035(4) 0.001(3) 0.002(3) -0.006(3) C28 0.020(3) 0.044(4) 0.043(4) -0.012(3) 0.006(3) 0.004(3) C2S 0.025(3) 0.052(5) 0.051(5) 0.014(3) 0.001(3) -0.009(3) C1S 0.025(3) 0.032(4) 0.029(3) -0.005(3) 0.002(3) -0.006(3) Cl1 0.0300(8) 0.0329(9) 0.0460(10) 0.0151(7) -0.0026(7) -0.0068(7) Cl2 0.0389(9) 0.0501(11) 0.0385(10) -0.0069(8) -0.0024(8) -0.0092(8) Cl3 0.0483(10) 0.0459(10) 0.0312(9) 0.0074(7) 0.0100(8) -0.0018(8) Cl4 0.0523(13) 0.174(3) 0.0527(14) 0.0562(15) -0.0054(11) -0.0367(14) Cl5 0.0739(14) 0.0463(12) 0.0649(13) -0.0033(10) 0.0228(11) 0.0138(10) Cl6 0.0364(9) 0.0364(10) 0.0828(14) 0.0009(10) -0.0069(9) 0.0030(8) _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 C1 1.885(5) . ? N1 C1 1.315(6) . ? N1 C5 1.444(6) . ? N1 C2 1.480(6) . ? N2 C1 1.328(6) . ? N2 C17 1.455(6) . ? N2 C4 1.462(6) . ? C2 C3 1.503(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.405(7) . ? C5 C10 1.404(7) . ? C6 C7 1.383(7) . ? C6 C11 1.528(7) . ? C7 C8 1.364(8) . ? C7 H7A 0.9500 . ? C8 C9 1.387(8) . ? C8 H8A 0.9500 . ? C9 C10 1.392(7) . ? C9 H9A 0.9500 . ? C10 C14 1.507(7) . ? C11 C12 1.505(8) . ? C11 C13 1.537(8) . ? C11 H11A 1.0000 . ? 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 C16 1.512(8) . ? C14 C15 1.534(8) . ? C14 H14A 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.403(7) . ? C17 C22 1.410(7) . ? C18 C19 1.392(7) . ? C18 C23 1.530(7) . ? C19 C20 1.384(8) . ? C19 H19A 0.9500 . ? C20 C21 1.373(8) . ? C20 H20A 0.9500 . ? C21 C22 1.397(8) . ? C21 H21A 0.9500 . ? C22 C26 1.507(7) . ? C23 C25 1.505(8) . ? C23 C24 1.528(8) . ? C23 H23A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C28 1.527(8) . ? C26 C27 1.532(8) . ? C26 H26A 1.0000 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C2S Cl4 1.732(7) . ? C2S Cl5 1.758(7) . ? C2S Cl6 1.769(7) . ? C2S H1SA 1.0000 . ? C1S Cl2 1.740(6) . ? C1S Cl3 1.758(6) . ? C1S Cl1 1.772(6) . ? C1S H2SA 1.0000 . ? 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 N1 C5 123.5(4) . . ? C1 N1 C2 121.2(4) . . ? C5 N1 C2 115.2(4) . . ? C1 N2 C17 122.6(4) . . ? C1 N2 C4 121.1(4) . . ? C17 N2 C4 115.9(4) . . ? N1 C1 N2 123.1(5) . . ? N1 C1 Br1 118.3(4) . . ? N2 C1 Br1 118.5(4) . . ? N1 C2 C3 110.2(4) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 109.0(4) . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N2 C4 C3 111.0(4) . . ? N2 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C10 123.4(5) . . ? C6 C5 N1 117.1(5) . . ? C10 C5 N1 119.3(5) . . ? C7 C6 C5 117.1(5) . . ? C7 C6 C11 121.2(5) . . ? C5 C6 C11 121.7(5) . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C7 C8 C9 120.8(5) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C8 C9 C10 121.2(5) . . ? C8 C9 H9A 119.4 . . ? C10 C9 H9A 119.4 . . ? C9 C10 C5 116.2(5) . . ? C9 C10 C14 121.2(5) . . ? C5 C10 C14 122.7(5) . . ? C12 C11 C6 111.8(5) . . ? C12 C11 C13 111.1(5) . . ? C6 C11 C13 111.4(5) . . ? C12 C11 H11A 107.4 . . ? C6 C11 H11A 107.4 . . ? C13 C11 H11A 107.4 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C10 112.2(5) . . ? C16 C14 C15 110.6(5) . . ? C10 C14 C15 111.4(5) . . ? C16 C14 H14A 107.5 . . ? C10 C14 H14A 107.5 . . ? C15 C14 H14A 107.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 123.4(5) . . ? C18 C17 N2 118.0(4) . . ? C22 C17 N2 118.4(5) . . ? C19 C18 C17 117.4(5) . . ? C19 C18 C23 120.7(5) . . ? C17 C18 C23 121.9(5) . . ? C20 C19 C18 120.5(5) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C21 C20 C19 120.6(5) . . ? C21 C20 H20A 119.7 . . ? C19 C20 H20A 119.7 . . ? C20 C21 C22 122.2(5) . . ? C20 C21 H21A 118.9 . . ? C22 C21 H21A 118.9 . . ? C21 C22 C17 115.7(5) . . ? C21 C22 C26 120.8(5) . . ? C17 C22 C26 123.5(5) . . ? C25 C23 C24 110.7(5) . . ? C25 C23 C18 112.5(5) . . ? C24 C23 C18 111.0(5) . . ? C25 C23 H23A 107.4 . . ? C24 C23 H23A 107.4 . . ? C18 C23 H23A 107.4 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 C28 111.5(5) . . ? C22 C26 C27 110.7(5) . . ? C28 C26 C27 110.5(5) . . ? C22 C26 H26A 108.0 . . ? C28 C26 H26A 108.0 . . ? C27 C26 H26A 108.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Cl4 C2S Cl5 110.1(4) . . ? Cl4 C2S Cl6 111.6(4) . . ? Cl5 C2S Cl6 108.0(4) . . ? Cl4 C2S H1SA 109.1 . . ? Cl5 C2S H1SA 109.1 . . ? Cl6 C2S H1SA 109.1 . . ? Cl2 C1S Cl3 112.5(3) . . ? Cl2 C1S Cl1 109.9(3) . . ? Cl3 C1S Cl1 109.9(3) . . ? Cl2 C1S H2SA 108.1 . . ? Cl3 C1S H2SA 108.1 . . ? Cl1 C1S H2SA 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 N2 -177.8(4) . . . . ? C2 N1 C1 N2 3.1(7) . . . . ? C5 N1 C1 Br1 6.2(6) . . . . ? C2 N1 C1 Br1 -172.9(3) . . . . ? C17 N2 C1 N1 -173.8(5) . . . . ? C4 N2 C1 N1 -1.7(7) . . . . ? C17 N2 C1 Br1 2.1(6) . . . . ? C4 N2 C1 Br1 174.3(3) . . . . ? C1 N1 C2 C3 -29.8(6) . . . . ? C5 N1 C2 C3 151.0(4) . . . . ? N1 C2 C3 C4 52.4(6) . . . . ? C1 N2 C4 C3 26.9(6) . . . . ? C17 N2 C4 C3 -160.4(4) . . . . ? C2 C3 C4 N2 -51.5(6) . . . . ? C1 N1 C5 C6 97.5(6) . . . . ? C2 N1 C5 C6 -83.3(6) . . . . ? C1 N1 C5 C10 -87.7(6) . . . . ? C2 N1 C5 C10 91.5(6) . . . . ? C10 C5 C6 C7 -2.0(8) . . . . ? N1 C5 C6 C7 172.5(4) . . . . ? C10 C5 C6 C11 176.8(5) . . . . ? N1 C5 C6 C11 -8.7(7) . . . . ? C5 C6 C7 C8 0.6(8) . . . . ? C11 C6 C7 C8 -178.2(5) . . . . ? C6 C7 C8 C9 2.3(8) . . . . ? C7 C8 C9 C10 -4.1(8) . . . . ? C8 C9 C10 C5 2.7(8) . . . . ? C8 C9 C10 C14 -177.0(5) . . . . ? C6 C5 C10 C9 0.3(8) . . . . ? N1 C5 C10 C9 -174.1(4) . . . . ? C6 C5 C10 C14 -179.9(5) . . . . ? N1 C5 C10 C14 5.6(8) . . . . ? C7 C6 C11 C12 -64.5(7) . . . . ? C5 C6 C11 C12 116.7(6) . . . . ? C7 C6 C11 C13 60.4(7) . . . . ? C5 C6 C11 C13 -118.3(6) . . . . ? C9 C10 C14 C16 -55.6(7) . . . . ? C5 C10 C14 C16 124.7(6) . . . . ? C9 C10 C14 C15 69.0(7) . . . . ? C5 C10 C14 C15 -110.7(6) . . . . ? C1 N2 C17 C18 -102.6(6) . . . . ? C4 N2 C17 C18 84.9(6) . . . . ? C1 N2 C17 C22 81.1(6) . . . . ? C4 N2 C17 C22 -91.4(6) . . . . ? C22 C17 C18 C19 -4.4(8) . . . . ? N2 C17 C18 C19 179.5(5) . . . . ? C22 C17 C18 C23 176.9(5) . . . . ? N2 C17 C18 C23 0.7(8) . . . . ? C17 C18 C19 C20 2.2(8) . . . . ? C23 C18 C19 C20 -179.0(5) . . . . ? C18 C19 C20 C21 0.1(9) . . . . ? C19 C20 C21 C22 -0.5(9) . . . . ? C20 C21 C22 C17 -1.5(9) . . . . ? C20 C21 C22 C26 178.6(5) . . . . ? C18 C17 C22 C21 4.0(8) . . . . ? N2 C17 C22 C21 -179.9(5) . . . . ? C18 C17 C22 C26 -176.0(5) . . . . ? N2 C17 C22 C26 0.1(8) . . . . ? C19 C18 C23 C25 36.7(7) . . . . ? C17 C18 C23 C25 -144.6(5) . . . . ? C19 C18 C23 C24 -88.0(6) . . . . ? C17 C18 C23 C24 90.7(6) . . . . ? C21 C22 C26 C28 57.2(7) . . . . ? C17 C22 C26 C28 -122.7(6) . . . . ? C21 C22 C26 C27 -66.2(7) . . . . ? C17 C22 C26 C27 113.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.900 _refine_diff_density_min -0.883 _refine_diff_density_rms 0.127