# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jan Reedijk' _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_section_title ; A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols ; loop_ _publ_author_name 'Jan Reedijk' 'Patrick Gamez' 'Zhengliang Lu.' 'Ilpo Mutikainen' 'Olivier Roubeau' ; J.S.Costa ; 'Simon J. Teat' 'Urho Turpeinen' # Attachment 'Compound_6a.CIF' data_test _database_code_depnum_ccdc_archive 'CCDC 676753' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 Cl N7 O' _chemical_formula_weight 469.93 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.644(5) _cell_length_b 8.9425(18) _cell_length_c 19.223(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.61(3) _cell_angle_gamma 90.00 _cell_volume 4539.8(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 17372 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.878 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details 'Mulabs, Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28018 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.87 _reflns_number_total 5398 _reflns_number_gt 4085 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. All hydrogens were found in difference Fourier maps and fixed at calculated positions on their riding atom. ; _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^)+(0.0482P)^2^+3.2373P] 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 5398 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 Cl1 Cl 0.235078(16) 0.38201(4) 0.05416(2) 0.03178(12) Uani 1 1 d . . . O20 O 0.26508(4) 0.87998(12) 0.14730(6) 0.0251(3) Uani 1 1 d . . . N4 N 0.19930(5) 0.85768(14) 0.05810(7) 0.0197(3) Uani 1 1 d . . . N2 N 0.18062(5) 0.61189(14) 0.01263(7) 0.0210(3) Uani 1 1 d . . . N7 N 0.13109(5) 0.81511(14) -0.02645(7) 0.0202(3) Uani 1 1 d . . . N6 N 0.25107(5) 0.65148(14) 0.10164(7) 0.0215(3) Uani 1 1 d . . . C8 C 0.12186(5) 0.97445(16) -0.03017(8) 0.0197(3) Uani 1 1 d . . . N24 N 0.32762(5) 1.21914(15) 0.26435(7) 0.0261(3) Uani 1 1 d . . . C5 C 0.23680(5) 0.79532(16) 0.09985(8) 0.0192(3) Uani 1 1 d . . . C3 C 0.17140(5) 0.75990(16) 0.01580(7) 0.0184(3) Uani 1 1 d . . . C25 C 0.37255(6) 1.20021(18) 0.30399(8) 0.0233(3) Uani 1 1 d . . . N29 N 0.45375(5) 1.28898(16) 0.35310(8) 0.0325(3) Uani 1 1 d . . . C28 C 0.40971(6) 1.32282(19) 0.31395(8) 0.0246(3) Uani 1 1 d . . . C15 C 0.05170(6) 0.67656(18) -0.04266(9) 0.0244(3) Uani 1 1 d . . . H15A H 0.0448 0.7121 0.0016 0.029 Uiso 1 1 calc R . . C14 C 0.09613(5) 0.71717(16) -0.06812(8) 0.0192(3) Uani 1 1 d . . . C33 C 0.39940(7) 1.4639(2) 0.28518(9) 0.0316(4) Uani 1 1 d . . . H33A H 0.3677 1.4843 0.2580 0.038 Uiso 1 1 calc R . . N23 N 0.30425(5) 1.08557(16) 0.26667(7) 0.0262(3) Uani 1 1 d . . . C1 C 0.22061(6) 0.57047(17) 0.05620(8) 0.0212(3) Uani 1 1 d . . . C16 C 0.01749(6) 0.58335(18) -0.08266(9) 0.0275(4) Uani 1 1 d . . . H16A H -0.0129 0.5549 -0.0655 0.033 Uiso 1 1 calc R . . C12 C 0.12676(6) 1.20670(19) -0.09072(10) 0.0327(4) Uani 1 1 d . . . H12A H 0.1343 1.2610 -0.1305 0.039 Uiso 1 1 calc R . . C9 C 0.10248(7) 1.04711(19) 0.02372(9) 0.0303(4) Uani 1 1 d . . . H9A H 0.0935 0.9922 0.0625 0.036 Uiso 1 1 calc R . . C19 C 0.10652(6) 0.66580(18) -0.13254(8) 0.0248(3) Uani 1 1 d . . . H19A H 0.1370 0.6936 -0.1496 0.030 Uiso 1 1 calc R . . C18 C 0.07186(7) 0.57306(19) -0.17204(9) 0.0296(4) Uani 1 1 d . . . H18A H 0.0787 0.5377 -0.2164 0.035 Uiso 1 1 calc R . . C17 C 0.02733(6) 0.53182(18) -0.14713(9) 0.0284(4) Uani 1 1 d . . . H17A H 0.0037 0.4684 -0.1743 0.034 Uiso 1 1 calc R . . C13 C 0.13393(6) 1.05306(19) -0.08768(9) 0.0277(4) Uani 1 1 d . . . H13A H 0.1470 1.0023 -0.1248 0.033 Uiso 1 1 calc R . . C11 C 0.10869(7) 1.28089(19) -0.03632(10) 0.0336(4) Uani 1 1 d . . . H11A H 0.1048 1.3865 -0.0379 0.040 Uiso 1 1 calc R . . C27 C 0.33274(6) 0.9850(2) 0.30626(9) 0.0301(4) Uani 1 1 d . . . H27A H 0.3238 0.8846 0.3150 0.036 Uiso 1 1 calc R . . C10 C 0.09625(7) 1.2011(2) 0.02063(10) 0.0375(4) Uani 1 1 d . . . H10A H 0.0834 1.2520 0.0578 0.045 Uiso 1 1 calc R . . C30 C 0.48860(7) 1.3982(2) 0.36308(11) 0.0386(5) Uani 1 1 d . . . H30A H 0.5201 1.3757 0.3903 0.046 Uiso 1 1 calc R . . C21 C 0.25025(7) 1.03443(19) 0.15425(10) 0.0352(4) Uani 1 1 d . . . H21A H 0.2154 1.0502 0.1304 0.042 Uiso 1 1 calc R . . H21B H 0.2734 1.1013 0.1325 0.042 Uiso 1 1 calc R . . C26 C 0.37722(6) 1.05506(19) 0.33155(9) 0.0285(4) Uani 1 1 d . . . H26A H 0.4051 1.0141 0.3613 0.034 Uiso 1 1 calc R . . C22 C 0.25278(6) 1.0686(2) 0.23152(10) 0.0357(4) Uani 1 1 d . . . H22A H 0.2338 1.1620 0.2373 0.043 Uiso 1 1 calc R . . H22B H 0.2360 0.9870 0.2544 0.043 Uiso 1 1 calc R . . C31 C 0.48155(7) 1.5404(2) 0.33650(10) 0.0368(4) Uani 1 1 d . . . H31A H 0.5074 1.6137 0.3453 0.044 Uiso 1 1 calc R . . C32 C 0.43595(8) 1.5739(2) 0.29661(10) 0.0381(4) Uani 1 1 d . . . H32A H 0.4298 1.6711 0.2774 0.046 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 Cl1 0.0359(2) 0.0199(2) 0.0373(2) -0.00245(16) -0.00369(17) 0.00898(15) O20 0.0243(6) 0.0227(6) 0.0254(6) -0.0039(5) -0.0079(4) 0.0015(4) N4 0.0202(6) 0.0185(6) 0.0194(6) 0.0000(5) -0.0009(5) 0.0001(5) N2 0.0234(6) 0.0184(6) 0.0203(7) -0.0004(5) -0.0003(5) 0.0018(5) N7 0.0223(6) 0.0159(6) 0.0205(6) -0.0014(5) -0.0039(5) 0.0009(5) N6 0.0213(6) 0.0224(7) 0.0200(7) 0.0002(5) 0.0001(5) 0.0038(5) C8 0.0186(7) 0.0174(7) 0.0212(8) -0.0005(6) -0.0042(5) 0.0009(5) N24 0.0249(7) 0.0282(7) 0.0240(7) -0.0067(6) -0.0009(5) -0.0013(5) C5 0.0190(7) 0.0226(8) 0.0157(7) 0.0000(6) 0.0014(5) -0.0010(5) C3 0.0197(7) 0.0194(7) 0.0159(7) 0.0008(6) 0.0017(5) 0.0008(5) C25 0.0212(7) 0.0301(9) 0.0185(8) -0.0059(6) 0.0020(6) 0.0007(6) N29 0.0218(7) 0.0333(8) 0.0404(9) -0.0052(7) -0.0034(6) 0.0007(6) C28 0.0233(8) 0.0302(9) 0.0201(8) -0.0062(6) 0.0021(6) -0.0004(6) C15 0.0259(8) 0.0249(8) 0.0220(8) -0.0005(6) 0.0019(6) 0.0008(6) C14 0.0210(7) 0.0158(7) 0.0194(7) -0.0003(6) -0.0027(6) 0.0017(5) C33 0.0332(9) 0.0373(10) 0.0230(8) 0.0015(7) -0.0010(7) -0.0027(7) N23 0.0235(7) 0.0305(7) 0.0238(7) -0.0102(6) -0.0003(5) -0.0019(5) C1 0.0239(7) 0.0202(7) 0.0198(8) 0.0007(6) 0.0034(6) 0.0028(6) C16 0.0222(8) 0.0281(9) 0.0314(9) 0.0023(7) 0.0003(6) -0.0033(6) C12 0.0316(9) 0.0271(9) 0.0387(10) 0.0122(8) 0.0022(7) -0.0015(7) C9 0.0416(10) 0.0252(9) 0.0247(9) 0.0015(7) 0.0062(7) 0.0057(7) C19 0.0247(8) 0.0260(8) 0.0238(8) -0.0006(6) 0.0031(6) -0.0002(6) C18 0.0375(9) 0.0289(9) 0.0213(8) -0.0067(7) 0.0003(7) -0.0005(7) C17 0.0319(9) 0.0225(8) 0.0276(9) -0.0008(7) -0.0077(7) -0.0043(6) C13 0.0285(8) 0.0276(9) 0.0272(9) 0.0033(7) 0.0041(6) 0.0027(6) C11 0.0336(9) 0.0176(8) 0.0460(11) 0.0011(7) -0.0081(8) 0.0017(6) C27 0.0299(9) 0.0290(9) 0.0313(9) -0.0041(7) 0.0034(7) -0.0015(7) C10 0.0498(11) 0.0271(9) 0.0347(10) -0.0059(8) 0.0028(8) 0.0113(8) C30 0.0241(9) 0.0428(11) 0.0470(12) -0.0091(9) -0.0020(8) -0.0048(7) C21 0.0387(10) 0.0228(9) 0.0385(10) -0.0057(7) -0.0157(8) 0.0025(7) C26 0.0266(8) 0.0310(9) 0.0271(9) -0.0006(7) 0.0005(6) 0.0019(6) C22 0.0215(8) 0.0377(10) 0.0454(11) -0.0172(8) -0.0050(7) 0.0005(7) C31 0.0354(10) 0.0403(11) 0.0354(10) -0.0070(8) 0.0074(8) -0.0147(8) C32 0.0486(11) 0.0359(10) 0.0296(10) 0.0040(8) 0.0043(8) -0.0096(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 Cl1 C1 1.7305(16) . ? O20 C5 1.3382(18) . ? O20 C21 1.448(2) . ? N4 C5 1.3195(19) . ? N4 C3 1.3483(19) . ? N2 C1 1.3181(19) . ? N2 C3 1.3490(19) . ? N7 C3 1.3513(18) . ? N7 C14 1.4418(18) . ? N7 C8 1.4462(19) . ? N6 C1 1.326(2) . ? N6 C5 1.3405(19) . ? C8 C9 1.380(2) . ? C8 C13 1.384(2) . ? N24 C25 1.342(2) . ? N24 N23 1.3505(19) . ? C25 C26 1.401(2) . ? C25 C28 1.473(2) . ? N29 C28 1.342(2) . ? N29 C30 1.344(2) . ? C28 C33 1.390(2) . ? C15 C14 1.388(2) . ? C15 C16 1.390(2) . ? C15 H15A 0.9500 . ? C14 C19 1.383(2) . ? C33 C32 1.382(2) . ? C33 H33A 0.9500 . ? N23 C27 1.346(2) . ? N23 C22 1.454(2) . ? C16 C17 1.380(2) . ? C16 H16A 0.9500 . ? C12 C11 1.378(3) . ? C12 C13 1.387(2) . ? C12 H12A 0.9500 . ? C9 C10 1.387(2) . ? C9 H9A 0.9500 . ? C19 C18 1.390(2) . ? C19 H19A 0.9500 . ? C18 C17 1.387(2) . ? C18 H18A 0.9500 . ? C17 H17A 0.9500 . ? C13 H13A 0.9500 . ? C11 C10 1.383(3) . ? C11 H11A 0.9500 . ? C27 C26 1.371(2) . ? C27 H27A 0.9500 . ? C10 H10A 0.9500 . ? C30 C31 1.374(3) . ? C30 H30A 0.9500 . ? C21 C22 1.509(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C26 H26A 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C31 C32 1.381(3) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O20 C21 117.82(12) . . ? C5 N4 C3 113.91(13) . . ? C1 N2 C3 112.56(12) . . ? C3 N7 C14 121.04(12) . . ? C3 N7 C8 120.40(12) . . ? C14 N7 C8 118.55(11) . . ? C1 N6 C5 111.14(13) . . ? C9 C8 C13 120.69(15) . . ? C9 C8 N7 120.33(14) . . ? C13 C8 N7 118.95(14) . . ? C25 N24 N23 104.49(13) . . ? N4 C5 O20 119.22(13) . . ? N4 C5 N6 127.62(13) . . ? O20 C5 N6 113.16(12) . . ? N4 C3 N2 125.06(13) . . ? N4 C3 N7 117.15(13) . . ? N2 C3 N7 117.79(13) . . ? N24 C25 C26 111.07(14) . . ? N24 C25 C28 120.91(15) . . ? C26 C25 C28 128.02(15) . . ? C28 N29 C30 116.90(16) . . ? N29 C28 C33 122.66(15) . . ? N29 C28 C25 115.34(15) . . ? C33 C28 C25 122.00(15) . . ? C14 C15 C16 119.30(15) . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C19 C14 C15 120.68(14) . . ? C19 C14 N7 120.54(14) . . ? C15 C14 N7 118.79(14) . . ? C32 C33 C28 119.03(16) . . ? C32 C33 H33A 120.5 . . ? C28 C33 H33A 120.5 . . ? C27 N23 N24 112.44(13) . . ? C27 N23 C22 128.30(15) . . ? N24 N23 C22 119.17(14) . . ? N2 C1 N6 129.62(14) . . ? N2 C1 Cl1 115.03(11) . . ? N6 C1 Cl1 115.35(11) . . ? C17 C16 C15 120.57(15) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? C11 C12 C13 120.32(16) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C8 C9 C10 119.34(16) . . ? C8 C9 H9A 120.3 . . ? C10 C9 H9A 120.3 . . ? C14 C19 C18 119.35(15) . . ? C14 C19 H19A 120.3 . . ? C18 C19 H19A 120.3 . . ? C17 C18 C19 120.47(16) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C16 C17 C18 119.63(15) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C8 C13 C12 119.44(16) . . ? C8 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C12 C11 C10 119.78(16) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? N23 C27 C26 106.93(15) . . ? N23 C27 H27A 126.5 . . ? C26 C27 H27A 126.5 . . ? C11 C10 C9 120.40(17) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? N29 C30 C31 124.18(17) . . ? N29 C30 H30A 117.9 . . ? C31 C30 H30A 117.9 . . ? O20 C21 C22 107.89(14) . . ? O20 C21 H21A 110.1 . . ? C22 C21 H21A 110.1 . . ? O20 C21 H21B 110.1 . . ? C22 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C27 C26 C25 105.08(15) . . ? C27 C26 H26A 127.5 . . ? C25 C26 H26A 127.5 . . ? N23 C22 C21 113.25(15) . . ? N23 C22 H22A 108.9 . . ? C21 C22 H22A 108.9 . . ? N23 C22 H22B 108.9 . . ? C21 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C30 C31 C32 118.33(16) . . ? C30 C31 H31A 120.8 . . ? C32 C31 H31A 120.8 . . ? C31 C32 C33 118.89(18) . . ? C31 C32 H32A 120.6 . . ? C33 C32 H32A 120.6 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.256 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.056 # Attachment 'Compound_6b.cif' #============================================================================= data_zl002 _database_code_depnum_ccdc_archive 'CCDC 676754' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H20 Cl N7 O' _chemical_formula_sum 'C25 H20 Cl N7 O' _chemical_formula_weight 469.93 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.500(2) _cell_length_b 9.483(2) _cell_length_c 15.043(3) _cell_angle_alpha 99.31(3) _cell_angle_beta 93.73(3) _cell_angle_gamma 102.40(3) _cell_volume 1162.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 373(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 4.22 _cell_measurement_theta_max 14.56 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(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 KappaCCD _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11933 _diffrn_reflns_av_R_equivalents 0.1386 _diffrn_reflns_av_sigmaI/netI 0.3327 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4212 _reflns_number_gt 1382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2002)' _computing_cell_refinement 'DirAx (Duisenberg 1992)' _computing_data_reduction 'COLLECT/EVAL (Nonius, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1990)' _computing_publication_material 'SHELXTL (Sheldrick, 1990)' _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^)+(0.0803P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4212 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2916 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1931 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 N1 N 1.0862(5) 0.4912(4) 0.3603(3) 0.0306(12) Uani 1 1 d . . . C2 C 1.1211(6) 0.3451(6) 0.3374(4) 0.0347(15) Uani 1 1 d . . . C3 C 1.2224(6) 0.3206(6) 0.2712(4) 0.0402(16) Uani 1 1 d . . . H3A H 1.2720 0.3967 0.2433 0.048 Uiso 1 1 calc R . . C4 C 1.2490(6) 0.1791(7) 0.2467(4) 0.0438(17) Uani 1 1 d . . . H4A H 1.3182 0.1617 0.2029 0.053 Uiso 1 1 calc R . . C5 C 1.1737(7) 0.0654(6) 0.2870(4) 0.0447(17) Uani 1 1 d . . . H5A H 1.1886 -0.0288 0.2686 0.054 Uiso 1 1 calc R . . C6 C 1.0747(7) 0.0922(6) 0.3558(4) 0.0465(17) Uani 1 1 d . . . H6A H 1.0265 0.0169 0.3847 0.056 Uiso 1 1 calc R . . C7 C 1.0495(7) 0.2328(7) 0.3803(4) 0.0458(17) Uani 1 1 d . . . H7A H 0.9839 0.2516 0.4259 0.055 Uiso 1 1 calc R . . C8 C 1.1961(6) 0.6044(6) 0.4266(4) 0.0331(15) Uani 1 1 d . . . C9 C 1.2921(6) 0.5612(6) 0.4921(4) 0.0369(16) Uani 1 1 d . . . H9A H 1.2856 0.4621 0.4923 0.044 Uiso 1 1 calc R . . C10 C 1.3987(7) 0.6688(7) 0.5579(4) 0.0444(17) Uani 1 1 d . . . H10A H 1.4625 0.6398 0.6009 0.053 Uiso 1 1 calc R . . C11 C 1.4093(7) 0.8169(7) 0.5590(4) 0.0499(18) Uani 1 1 d . . . H11A H 1.4756 0.8872 0.6041 0.060 Uiso 1 1 calc R . . C12 C 1.3193(7) 0.8586(7) 0.4917(5) 0.0439(17) Uani 1 1 d . . . H12A H 1.3289 0.9579 0.4909 0.053 Uiso 1 1 calc R . . C13 C 1.2144(6) 0.7546(6) 0.4250(4) 0.0349(15) Uani 1 1 d . . . H13A H 1.1569 0.7850 0.3798 0.042 Uiso 1 1 calc R . . C14 C 0.9369(6) 0.5038(6) 0.3241(4) 0.0318(15) Uani 1 1 d . . . N15 N 0.8823(5) 0.6272(5) 0.3558(3) 0.0366(13) Uani 1 1 d . . . C16 C 0.7335(7) 0.6191(6) 0.3159(4) 0.0348(15) Uani 1 1 d . . . N17 N 0.6384(5) 0.5143(5) 0.2519(3) 0.0371(13) Uani 1 1 d . . . C18 C 0.7113(7) 0.4028(6) 0.2255(4) 0.0344(15) Uani 1 1 d . . . N19 N 0.8544(6) 0.3897(5) 0.2585(3) 0.0336(12) Uani 1 1 d . . . Cl20 Cl 0.65393(18) 0.76988(17) 0.35693(11) 0.0591(6) Uani 1 1 d . . . O21 O 0.6212(4) 0.2955(4) 0.1605(3) 0.0408(11) Uani 1 1 d . . . C22 C 0.6958(6) 0.1741(5) 0.1266(4) 0.0372(16) Uani 1 1 d . . . H22B H 0.6123 0.0901 0.0966 0.045 Uiso 1 1 calc R . . H22A H 0.7508 0.1456 0.1770 0.045 Uiso 1 1 calc R . . C23 C 0.8171(6) 0.2200(6) 0.0599(4) 0.0390(16) Uani 1 1 d . . . H23A H 0.8933 0.3103 0.0881 0.047 Uiso 1 1 calc R . . H23B H 0.8777 0.1448 0.0459 0.047 Uiso 1 1 calc R . . N24 N 0.7360(5) 0.2425(5) -0.0251(3) 0.0328(12) Uani 1 1 d . . . N25 N 0.6655(6) 0.1170(5) -0.0890(4) 0.0450(14) Uani 1 1 d . . . C26 C 0.5941(7) 0.1672(7) -0.1551(4) 0.0463(18) Uani 1 1 d . . . H26A H 0.5374 0.1079 -0.2077 0.056 Uiso 1 1 calc R . . C27 C 0.6146(7) 0.3202(7) -0.1358(4) 0.0400(16) Uani 1 1 d . . . H27A H 0.5754 0.3780 -0.1722 0.048 Uiso 1 1 calc R . . C28 C 0.7053(6) 0.3691(6) -0.0510(4) 0.0312(15) Uani 1 1 d . . . C29 C 0.7589(7) 0.5204(6) 0.0007(4) 0.0358(16) Uani 1 1 d . . . N30 N 0.8732(6) 0.5496(5) 0.0726(3) 0.0412(14) Uani 1 1 d . . . C31 C 0.9225(6) 0.6905(7) 0.1169(4) 0.0419(16) Uani 1 1 d . . . H31A H 1.0000 0.7111 0.1666 0.050 Uiso 1 1 calc R . . C32 C 0.8628(7) 0.8074(6) 0.0917(5) 0.0460(17) Uani 1 1 d . . . H32A H 0.9015 0.9030 0.1230 0.055 Uiso 1 1 calc R . . C33 C 0.7445(8) 0.7758(7) 0.0187(4) 0.0520(19) Uani 1 1 d . . . H33A H 0.7006 0.8498 0.0008 0.062 Uiso 1 1 calc R . . C34 C 0.6925(7) 0.6316(6) -0.0272(4) 0.0419(17) Uani 1 1 d . . . H34A H 0.6138 0.6088 -0.0764 0.050 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 N1 0.024(3) 0.027(3) 0.036(3) -0.006(2) -0.002(2) 0.006(2) C2 0.028(4) 0.033(4) 0.041(4) -0.002(3) -0.001(3) 0.011(3) C3 0.041(4) 0.033(4) 0.048(4) 0.004(3) 0.012(3) 0.012(3) C4 0.033(4) 0.046(4) 0.054(5) 0.003(4) 0.016(3) 0.014(3) C5 0.037(4) 0.031(4) 0.063(5) -0.002(4) 0.002(4) 0.010(3) C6 0.047(4) 0.046(4) 0.050(4) 0.016(3) 0.019(4) 0.011(3) C7 0.043(4) 0.043(4) 0.059(5) 0.008(4) 0.018(4) 0.023(3) C8 0.019(3) 0.042(4) 0.038(4) 0.000(3) 0.007(3) 0.010(3) C9 0.028(4) 0.037(4) 0.038(4) -0.007(3) -0.004(3) 0.005(3) C10 0.036(4) 0.058(5) 0.040(4) 0.011(4) 0.004(3) 0.012(4) C11 0.042(4) 0.056(5) 0.042(5) -0.008(4) 0.007(4) 0.002(4) C12 0.032(4) 0.040(4) 0.056(5) -0.002(4) 0.013(4) 0.007(3) C13 0.023(4) 0.035(4) 0.048(4) 0.006(3) 0.004(3) 0.007(3) C14 0.023(4) 0.047(4) 0.025(4) 0.005(3) 0.003(3) 0.007(3) N15 0.037(3) 0.039(3) 0.039(3) 0.002(2) 0.010(3) 0.023(3) C16 0.034(4) 0.040(4) 0.038(4) 0.009(3) 0.013(3) 0.020(3) N17 0.031(3) 0.044(3) 0.034(3) -0.008(3) 0.002(3) 0.015(3) C18 0.029(4) 0.039(4) 0.039(4) 0.006(3) 0.013(3) 0.014(3) N19 0.028(3) 0.034(3) 0.036(3) 0.001(3) 0.004(3) 0.007(2) Cl20 0.0536(11) 0.0594(12) 0.0674(13) -0.0111(9) 0.0033(9) 0.0374(9) O21 0.034(2) 0.035(3) 0.047(3) -0.007(2) 0.001(2) 0.007(2) C22 0.038(4) 0.025(4) 0.047(4) -0.002(3) 0.010(3) 0.008(3) C23 0.041(4) 0.039(4) 0.043(4) 0.007(3) 0.003(4) 0.022(3) N24 0.028(3) 0.035(3) 0.032(3) -0.004(3) 0.000(3) 0.009(3) N25 0.047(3) 0.036(3) 0.046(4) -0.007(3) 0.002(3) 0.010(3) C26 0.049(4) 0.051(5) 0.043(5) 0.006(4) 0.003(4) 0.022(4) C27 0.046(4) 0.042(4) 0.033(4) 0.005(3) 0.005(3) 0.012(3) C28 0.033(4) 0.039(4) 0.027(4) 0.004(3) 0.007(3) 0.020(3) C29 0.025(4) 0.027(4) 0.050(5) -0.010(3) 0.014(3) 0.004(3) N30 0.037(3) 0.031(3) 0.048(4) -0.006(3) 0.006(3) 0.001(3) C31 0.039(4) 0.041(4) 0.044(4) 0.002(4) 0.009(3) 0.007(3) C32 0.044(4) 0.030(4) 0.063(5) 0.002(4) 0.017(4) 0.010(3) C33 0.048(5) 0.050(5) 0.060(5) 0.002(4) -0.001(4) 0.023(4) C34 0.038(4) 0.034(4) 0.050(4) -0.006(4) 0.006(3) 0.009(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 N1 C14 1.385(6) . ? N1 C8 1.456(6) . ? N1 C2 1.470(6) . ? C2 C7 1.384(7) . ? C2 C3 1.382(6) . ? C3 C4 1.404(7) . ? C3 H3A 0.9300 . ? C4 C5 1.380(7) . ? C4 H4A 0.9300 . ? C5 C6 1.401(7) . ? C5 H5A 0.9300 . ? C6 C7 1.391(7) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C13 1.404(7) . ? C8 C9 1.405(7) . ? C9 C10 1.414(7) . ? C9 H9A 0.9300 . ? C10 C11 1.385(7) . ? C10 H10A 0.9300 . ? C11 C12 1.387(7) . ? C11 H11A 0.9300 . ? C12 C13 1.400(7) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 N19 1.368(6) . ? C14 N15 1.377(6) . ? N15 C16 1.345(6) . ? C16 N17 1.346(6) . ? C16 Cl20 1.751(5) . ? N17 C18 1.355(6) . ? C18 N19 1.323(6) . ? C18 O21 1.350(6) . ? O21 C22 1.467(5) . ? C22 C23 1.531(6) . ? C22 H22B 0.9700 . ? C22 H22A 0.9700 . ? C23 N24 1.482(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N24 C28 1.390(6) . ? N24 N25 1.395(5) . ? N25 C26 1.335(6) . ? C26 C27 1.402(7) . ? C26 H26A 0.9300 . ? C27 C28 1.401(7) . ? C27 H27A 0.9300 . ? C28 C29 1.477(7) . ? C29 N30 1.358(6) . ? C29 C34 1.404(7) . ? N30 C31 1.357(6) . ? C31 C32 1.408(7) . ? C31 H31A 0.9300 . ? C32 C33 1.388(7) . ? C32 H32A 0.9300 . ? C33 C34 1.392(7) . ? C33 H33A 0.9300 . ? C34 H34A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N1 C8 124.5(4) . . ? C14 N1 C2 115.4(4) . . ? C8 N1 C2 119.6(4) . . ? C7 C2 C3 120.7(5) . . ? C7 C2 N1 120.0(5) . . ? C3 C2 N1 119.3(5) . . ? C2 C3 C4 119.0(5) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C5 C4 C3 120.7(5) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 119.9(5) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 119.2(6) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C2 C7 C6 120.5(5) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C13 C8 C9 118.9(5) . . ? C13 C8 N1 122.4(5) . . ? C9 C8 N1 118.7(5) . . ? C8 C9 C10 119.9(5) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 120.8(6) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C12 C11 C10 118.9(6) . . ? C12 C11 H11A 120.5 . . ? C10 C11 H11A 120.5 . . ? C11 C12 C13 121.5(6) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C12 C13 C8 119.9(6) . . ? C12 C13 H13A 120.1 . . ? C8 C13 H13A 120.1 . . ? N19 C14 N15 125.0(5) . . ? N19 C14 N1 116.3(5) . . ? N15 C14 N1 118.7(5) . . ? C16 N15 C14 110.9(5) . . ? N15 C16 N17 130.4(5) . . ? N15 C16 Cl20 113.1(4) . . ? N17 C16 Cl20 116.5(4) . . ? C16 N17 C18 111.6(5) . . ? N19 C18 N17 126.6(5) . . ? N19 C18 O21 119.5(5) . . ? N17 C18 O21 113.8(5) . . ? C18 N19 C14 115.4(5) . . ? C18 O21 C22 116.5(4) . . ? O21 C22 C23 110.4(4) . . ? O21 C22 H22B 109.6 . . ? C23 C22 H22B 109.6 . . ? O21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? H22B C22 H22A 108.1 . . ? N24 C23 C22 111.9(4) . . ? N24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? N24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C28 N24 N25 112.1(5) . . ? C28 N24 C23 130.8(5) . . ? N25 N24 C23 116.9(5) . . ? C26 N25 N24 104.4(5) . . ? N25 C26 C27 112.0(6) . . ? N25 C26 H26A 124.0 . . ? C27 C26 H26A 124.0 . . ? C26 C27 C28 106.9(5) . . ? C26 C27 H27A 126.6 . . ? C28 C27 H27A 126.6 . . ? N24 C28 C27 104.6(5) . . ? N24 C28 C29 126.7(5) . . ? C27 C28 C29 128.7(5) . . ? N30 C29 C34 121.5(5) . . ? N30 C29 C28 119.5(5) . . ? C34 C29 C28 119.0(6) . . ? C31 N30 C29 117.8(5) . . ? N30 C31 C32 123.6(6) . . ? N30 C31 H31A 118.2 . . ? C32 C31 H31A 118.2 . . ? C33 C32 C31 118.0(6) . . ? C33 C32 H32A 121.0 . . ? C31 C32 H32A 121.0 . . ? C32 C33 C34 119.0(6) . . ? C32 C33 H33A 120.5 . . ? C34 C33 H33A 120.5 . . ? C33 C34 C29 120.1(6) . . ? C33 C34 H34A 119.9 . . ? C29 C34 H34A 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N1 C2 C7 -76.3(6) . . . . ? C8 N1 C2 C7 95.9(6) . . . . ? C14 N1 C2 C3 102.0(6) . . . . ? C8 N1 C2 C3 -85.8(6) . . . . ? C7 C2 C3 C4 1.3(8) . . . . ? N1 C2 C3 C4 -177.0(5) . . . . ? C2 C3 C4 C5 0.9(8) . . . . ? C3 C4 C5 C6 -2.7(9) . . . . ? C4 C5 C6 C7 2.2(8) . . . . ? C3 C2 C7 C6 -1.7(8) . . . . ? N1 C2 C7 C6 176.6(5) . . . . ? C5 C6 C7 C2 0.0(8) . . . . ? C14 N1 C8 C13 -36.4(7) . . . . ? C2 N1 C8 C13 152.2(5) . . . . ? C14 N1 C8 C9 146.3(5) . . . . ? C2 N1 C8 C9 -25.2(7) . . . . ? C13 C8 C9 C10 3.2(7) . . . . ? N1 C8 C9 C10 -179.3(4) . . . . ? C8 C9 C10 C11 0.4(8) . . . . ? C9 C10 C11 C12 -3.1(8) . . . . ? C10 C11 C12 C13 2.2(8) . . . . ? C11 C12 C13 C8 1.4(8) . . . . ? C9 C8 C13 C12 -4.1(7) . . . . ? N1 C8 C13 C12 178.6(4) . . . . ? C8 N1 C14 N19 176.2(4) . . . . ? C2 N1 C14 N19 -12.0(7) . . . . ? C8 N1 C14 N15 -4.0(7) . . . . ? C2 N1 C14 N15 167.8(4) . . . . ? N19 C14 N15 C16 2.0(7) . . . . ? N1 C14 N15 C16 -177.8(5) . . . . ? C14 N15 C16 N17 -1.3(8) . . . . ? C14 N15 C16 Cl20 177.5(3) . . . . ? N15 C16 N17 C18 -0.9(8) . . . . ? Cl20 C16 N17 C18 -179.6(4) . . . . ? C16 N17 C18 N19 2.7(7) . . . . ? C16 N17 C18 O21 -179.2(5) . . . . ? N17 C18 N19 C14 -2.1(8) . . . . ? O21 C18 N19 C14 179.9(4) . . . . ? N15 C14 N19 C18 -0.6(7) . . . . ? N1 C14 N19 C18 179.2(4) . . . . ? N19 C18 O21 C22 -3.9(7) . . . . ? N17 C18 O21 C22 177.9(4) . . . . ? C18 O21 C22 C23 -78.1(6) . . . . ? O21 C22 C23 N24 -68.1(5) . . . . ? C22 C23 N24 C28 94.4(6) . . . . ? C22 C23 N24 N25 -79.8(5) . . . . ? C28 N24 N25 C26 1.2(5) . . . . ? C23 N24 N25 C26 176.4(4) . . . . ? N24 N25 C26 C27 -0.5(6) . . . . ? N25 C26 C27 C28 -0.2(6) . . . . ? N25 N24 C28 C27 -1.3(5) . . . . ? C23 N24 C28 C27 -175.7(4) . . . . ? N25 N24 C28 C29 179.0(4) . . . . ? C23 N24 C28 C29 4.6(8) . . . . ? C26 C27 C28 N24 0.9(5) . . . . ? C26 C27 C28 C29 -179.4(5) . . . . ? N24 C28 C29 N30 13.1(7) . . . . ? C27 C28 C29 N30 -166.5(5) . . . . ? N24 C28 C29 C34 -168.3(5) . . . . ? C27 C28 C29 C34 12.1(8) . . . . ? C34 C29 N30 C31 -0.3(7) . . . . ? C28 C29 N30 C31 178.3(4) . . . . ? C29 N30 C31 C32 -0.7(7) . . . . ? N30 C31 C32 C33 1.5(8) . . . . ? C31 C32 C33 C34 -1.2(8) . . . . ? C32 C33 C34 C29 0.3(8) . . . . ? N30 C29 C34 C33 0.5(8) . . . . ? C28 C29 C34 C33 -178.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.284 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.069 # Attachment 'Compound_7a.CIF' data_7a _database_code_depnum_ccdc_archive 'CCDC 676755' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H78 N18 O5' _chemical_formula_weight 1227.48 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7743(16) _cell_length_b 29.216(6) _cell_length_c 14.248(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.85(3) _cell_angle_gamma 90.00 _cell_volume 3236.0(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details MULABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13021 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.54 _reflns_number_total 7332 _reflns_number_gt 5054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. The solvent water oxygen atom is partially occupied (0.5) and was refined with displacement parameters restrains. Hydrogens were found in difference Fourier maps and placed geometrically on their riding atom. Water hydrogens could not be found nor placed and are therefore missing in the present structural model. ; _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^)+(0.0741P)^2^+0.6754P] 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 7332 _refine_ls_number_parameters 415 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0835 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1549 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.059 _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 N1 N 0.44109(17) 0.45608(4) 0.08381(9) 0.0283(3) Uani 1 1 d . . . C2 C 0.5674(2) 0.42883(5) 0.05005(11) 0.0270(4) Uani 1 1 d . . . N3 N 0.59427(17) 0.38497(4) 0.07417(9) 0.0277(3) Uani 1 1 d . . . C4 C 0.4832(2) 0.36853(5) 0.13626(11) 0.0266(3) Uani 1 1 d . . . N5 N 0.35171(17) 0.39166(4) 0.17432(9) 0.0284(3) Uani 1 1 d . . . C6 C 0.3432(2) 0.43462(5) 0.14473(11) 0.0269(3) Uani 1 1 d . . . N7 N 0.67467(18) 0.44793(5) -0.01226(10) 0.0335(3) Uani 1 1 d . . . H7A H 0.6729 0.4778 -0.0201 0.040 Uiso 1 1 calc R . . C8 C 0.7943(2) 0.42034(6) -0.06733(12) 0.0302(4) Uani 1 1 d . . . H8A H 0.8174 0.3910 -0.0333 0.036 Uiso 1 1 calc R . . C9 C 0.9625(2) 0.44520(6) -0.08042(12) 0.0305(4) Uani 1 1 d . . . H9A H 1.0122 0.4529 -0.0180 0.037 Uiso 1 1 calc R . . H9B H 0.9401 0.4742 -0.1142 0.037 Uiso 1 1 calc R . . C10 C 1.0941(2) 0.41690(6) -0.13544(12) 0.0334(4) Uani 1 1 d . . . C11 C 1.2348(3) 0.44894(7) -0.17088(17) 0.0532(6) Uani 1 1 d . . . H11A H 1.3198 0.4312 -0.2056 0.080 Uiso 1 1 calc R . . H11B H 1.2914 0.4641 -0.1173 0.080 Uiso 1 1 calc R . . H11C H 1.1833 0.4721 -0.2124 0.080 Uiso 1 1 calc R . . C12 C 1.1752(2) 0.37945(6) -0.07408(13) 0.0405(4) Uani 1 1 d . . . H12A H 1.0851 0.3588 -0.0520 0.061 Uiso 1 1 calc R . . H12B H 1.2342 0.3935 -0.0201 0.061 Uiso 1 1 calc R . . H12C H 1.2583 0.3621 -0.1109 0.061 Uiso 1 1 calc R . . N13 N 1.0088(2) 0.39498(5) -0.21874(10) 0.0390(4) Uani 1 1 d . . . O14 O 1.1118(2) 0.37598(5) -0.27756(9) 0.0572(4) Uani 1 1 d . . . C15 C 0.8281(3) 0.37796(7) -0.22171(13) 0.0443(5) Uani 1 1 d . . . C16 C 0.8227(3) 0.32882(7) -0.18505(17) 0.0538(6) Uani 1 1 d . . . H16A H 0.8968 0.3094 -0.2234 0.081 Uiso 1 1 calc R . . H16B H 0.7043 0.3174 -0.1886 0.081 Uiso 1 1 calc R . . H16C H 0.8636 0.3282 -0.1197 0.081 Uiso 1 1 calc R . . C17 C 0.7658(4) 0.37865(11) -0.32406(17) 0.0900(10) Uani 1 1 d . . . H17A H 0.8389 0.3586 -0.3615 0.135 Uiso 1 1 calc R . . H17B H 0.7722 0.4100 -0.3485 0.135 Uiso 1 1 calc R . . H17C H 0.6466 0.3679 -0.3278 0.135 Uiso 1 1 calc R . . C18 C 0.7158(3) 0.40950(7) -0.16265(14) 0.0430(5) Uani 1 1 d . . . H18A H 0.6964 0.4385 -0.1973 0.052 Uiso 1 1 calc R . . H18B H 0.6025 0.3948 -0.1538 0.052 Uiso 1 1 calc R . . O19 O 0.21569(15) 0.46133(4) 0.17747(8) 0.0330(3) Uani 1 1 d . . . C20 C 0.1052(2) 0.44281(6) 0.24823(11) 0.0318(4) Uani 1 1 d . . . H20A H 0.0554 0.4683 0.2848 0.038 Uiso 1 1 calc R . . H20B H 0.1744 0.4236 0.2919 0.038 Uiso 1 1 calc R . . C21 C -0.0391(2) 0.41426(7) 0.20642(12) 0.0390(4) Uani 1 1 d . . . H21A H -0.1002 0.4317 0.1566 0.047 Uiso 1 1 calc R . . H21B H 0.0078 0.3860 0.1784 0.047 Uiso 1 1 calc R . . N22 N -0.15638(19) 0.40288(5) 0.28115(10) 0.0340(3) Uani 1 1 d . . . C23 C -0.1368(3) 0.36981(7) 0.34680(13) 0.0417(4) Uani 1 1 d . . . H23A H -0.0500 0.3469 0.3484 0.050 Uiso 1 1 calc R . . C24 C -0.2641(3) 0.37537(7) 0.41004(13) 0.0421(5) Uani 1 1 d . . . H24A H -0.2857 0.3572 0.4639 0.050 Uiso 1 1 calc R . . C25 C -0.3569(2) 0.41372(6) 0.37860(12) 0.0342(4) Uani 1 1 d . . . N26 N -0.28978(19) 0.43087(5) 0.30005(10) 0.0349(3) Uani 1 1 d . . . C27 C -0.5089(3) 0.43462(7) 0.42143(13) 0.0424(5) Uani 1 1 d . . . N28 N -0.5781(3) 0.41022(7) 0.49149(13) 0.0631(6) Uani 1 1 d . . . C29 C -0.7126(4) 0.42787(14) 0.5351(2) 0.0859(10) Uani 1 1 d . . . H29A H -0.7622 0.4107 0.5844 0.103 Uiso 1 1 calc R . . C30 C -0.7833(4) 0.46899(15) 0.5134(2) 0.0911(11) Uani 1 1 d . . . H30A H -0.8790 0.4803 0.5471 0.109 Uiso 1 1 calc R . . C31 C -0.7140(3) 0.49398(10) 0.4419(2) 0.0757(8) Uani 1 1 d . . . H31A H -0.7610 0.5229 0.4253 0.091 Uiso 1 1 calc R . . C32 C -0.5732(3) 0.47640(8) 0.39356(16) 0.0531(6) Uani 1 1 d . . . H32A H -0.5237 0.4928 0.3431 0.064 Uiso 1 1 calc R . . N33 N 0.50544(18) 0.32344(4) 0.16099(10) 0.0306(3) Uani 1 1 d . . . C34 C 0.4054(2) 0.30012(6) 0.23054(12) 0.0321(4) Uani 1 1 d . . . C35 C 0.3591(3) 0.25475(6) 0.21375(15) 0.0430(5) Uani 1 1 d . . . H35A H 0.3894 0.2404 0.1565 0.052 Uiso 1 1 calc R . . C36 C 0.2688(3) 0.23066(7) 0.28076(17) 0.0535(6) Uani 1 1 d . . . H36A H 0.2366 0.1998 0.2691 0.064 Uiso 1 1 calc R . . C37 C 0.2256(3) 0.25107(7) 0.36381(17) 0.0524(6) Uani 1 1 d . . . H37A H 0.1628 0.2344 0.4092 0.063 Uiso 1 1 calc R . . C38 C 0.2733(3) 0.29578(7) 0.38128(14) 0.0446(5) Uani 1 1 d . . . H38A H 0.2441 0.3098 0.4390 0.054 Uiso 1 1 calc R . . C39 C 0.3638(2) 0.32035(6) 0.31478(12) 0.0362(4) Uani 1 1 d . . . H39A H 0.3971 0.3511 0.3272 0.043 Uiso 1 1 calc R . . C40 C 0.6281(2) 0.29603(5) 0.11054(12) 0.0322(4) Uani 1 1 d . . . C41 C 0.7811(3) 0.28408(7) 0.15297(15) 0.0441(5) Uani 1 1 d . . . H41A H 0.8105 0.2954 0.2136 0.053 Uiso 1 1 calc R . . C42 C 0.8937(3) 0.25488(8) 0.1054(2) 0.0603(6) Uani 1 1 d . . . H42A H 1.0014 0.2468 0.1330 0.072 Uiso 1 1 calc R . . C43 C 0.8474(3) 0.23819(7) 0.01904(19) 0.0604(7) Uani 1 1 d . . . H43A H 0.9228 0.2179 -0.0124 0.073 Uiso 1 1 calc R . . C44 C 0.6951(4) 0.25008(7) -0.02272(17) 0.0614(7) Uani 1 1 d . . . H44A H 0.6647 0.2382 -0.0827 0.074 Uiso 1 1 calc R . . C45 C 0.5854(3) 0.27945(6) 0.02258(14) 0.0473(5) Uani 1 1 d . . . H45A H 0.4801 0.2883 -0.0068 0.057 Uiso 1 1 calc R . . O46 O 1.3423(11) 0.3363(2) -0.4074(5) 0.183(3) Uani 0.50 1 d PU . . 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 N1 0.0259(7) 0.0226(7) 0.0367(8) 0.0023(6) 0.0082(6) 0.0017(5) C2 0.0239(8) 0.0227(8) 0.0346(8) -0.0007(7) 0.0043(7) -0.0004(6) N3 0.0249(7) 0.0223(7) 0.0360(7) 0.0009(6) 0.0036(6) -0.0002(5) C4 0.0246(8) 0.0231(8) 0.0321(8) 0.0017(7) -0.0008(7) -0.0006(6) N5 0.0253(7) 0.0250(7) 0.0351(7) 0.0040(6) 0.0035(6) -0.0001(5) C6 0.0227(8) 0.0265(8) 0.0316(8) 0.0006(7) 0.0037(6) 0.0006(6) N7 0.0325(8) 0.0194(7) 0.0491(9) 0.0023(6) 0.0176(7) 0.0028(6) C8 0.0270(9) 0.0245(8) 0.0396(9) -0.0012(7) 0.0101(7) 0.0036(7) C9 0.0304(9) 0.0252(8) 0.0360(9) -0.0001(7) 0.0074(7) 0.0017(7) C10 0.0306(10) 0.0306(9) 0.0394(9) -0.0011(7) 0.0087(7) 0.0039(7) C11 0.0386(12) 0.0438(11) 0.0780(15) 0.0039(11) 0.0262(11) 0.0016(9) C12 0.0353(10) 0.0360(10) 0.0502(11) -0.0054(8) -0.0020(8) 0.0091(8) N13 0.0464(10) 0.0403(9) 0.0307(7) -0.0005(7) 0.0117(7) 0.0121(7) O14 0.0703(11) 0.0592(9) 0.0430(8) -0.0050(7) 0.0274(7) 0.0167(8) C15 0.0436(12) 0.0491(12) 0.0398(10) -0.0120(9) -0.0065(9) 0.0099(9) C16 0.0450(13) 0.0410(11) 0.0756(15) -0.0241(10) 0.0037(11) -0.0016(9) C17 0.104(2) 0.112(2) 0.0532(14) -0.0307(15) -0.0323(15) 0.0383(19) C18 0.0329(10) 0.0429(11) 0.0532(11) -0.0085(9) -0.0042(9) 0.0096(8) O19 0.0295(7) 0.0301(6) 0.0400(7) 0.0056(5) 0.0133(5) 0.0052(5) C20 0.0277(9) 0.0370(9) 0.0308(8) 0.0004(7) 0.0080(7) -0.0014(7) C21 0.0306(10) 0.0546(12) 0.0319(9) -0.0029(8) 0.0071(7) -0.0052(8) N22 0.0285(8) 0.0410(8) 0.0327(7) -0.0012(7) 0.0054(6) -0.0047(6) C23 0.0395(11) 0.0405(10) 0.0452(10) 0.0015(9) 0.0017(9) 0.0008(8) C24 0.0493(12) 0.0411(11) 0.0360(10) 0.0052(8) 0.0071(8) -0.0076(9) C25 0.0331(10) 0.0382(10) 0.0316(9) -0.0061(7) 0.0054(7) -0.0099(8) N26 0.0289(8) 0.0410(8) 0.0349(8) -0.0012(6) 0.0045(6) -0.0037(6) C27 0.0367(11) 0.0516(12) 0.0391(10) -0.0154(9) 0.0057(8) -0.0132(9) N28 0.0566(13) 0.0855(14) 0.0479(10) -0.0154(10) 0.0261(9) -0.0244(11) C29 0.0611(18) 0.131(3) 0.0660(17) -0.0344(18) 0.0333(14) -0.0303(19) C30 0.0418(15) 0.149(3) 0.083(2) -0.060(2) 0.0179(14) -0.0115(19) C31 0.0466(15) 0.0868(19) 0.093(2) -0.0495(17) -0.0144(14) 0.0115(13) C32 0.0393(12) 0.0574(13) 0.0625(13) -0.0199(11) -0.0040(10) -0.0021(10) N33 0.0302(8) 0.0215(7) 0.0402(8) 0.0050(6) 0.0059(6) -0.0003(6) C34 0.0248(9) 0.0273(9) 0.0440(10) 0.0103(7) -0.0017(7) -0.0021(7) C35 0.0402(11) 0.0309(10) 0.0580(12) 0.0051(9) 0.0037(9) -0.0054(8) C36 0.0481(13) 0.0320(10) 0.0807(16) 0.0150(11) 0.0075(11) -0.0111(9) C37 0.0418(12) 0.0461(12) 0.0696(14) 0.0248(11) 0.0130(11) -0.0041(9) C38 0.0409(12) 0.0455(12) 0.0478(11) 0.0152(9) 0.0064(9) 0.0031(9) C39 0.0333(10) 0.0332(9) 0.0421(10) 0.0088(8) 0.0005(8) -0.0010(7) C40 0.0318(9) 0.0199(8) 0.0451(10) 0.0048(7) 0.0056(8) -0.0005(7) C41 0.0347(11) 0.0398(11) 0.0578(12) 0.0081(9) 0.0000(9) 0.0018(8) C42 0.0373(12) 0.0477(13) 0.0960(19) 0.0180(13) 0.0084(12) 0.0121(10) C43 0.0652(16) 0.0362(11) 0.0807(17) 0.0010(11) 0.0319(14) 0.0082(11) C44 0.087(2) 0.0357(11) 0.0618(14) -0.0105(10) 0.0155(13) 0.0029(12) C45 0.0575(14) 0.0325(10) 0.0519(12) -0.0063(9) -0.0006(10) 0.0034(9) O46 0.229(7) 0.160(5) 0.164(5) 0.026(4) 0.063(5) 0.041(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.321(2) . ? N1 C2 1.358(2) . ? C2 N3 1.342(2) . ? C2 N7 1.348(2) . ? N3 C4 1.335(2) . ? C4 N5 1.346(2) . ? C4 N33 1.374(2) . ? N5 C6 1.325(2) . ? C6 O19 1.3503(19) . ? N7 C8 1.467(2) . ? N7 H7A 0.8800 . ? C8 C9 1.510(2) . ? C8 C18 1.514(3) . ? C8 H8A 1.0000 . ? C9 C10 1.539(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N13 1.495(2) . ? C10 C12 1.531(2) . ? C10 C11 1.531(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N13 O14 1.2930(19) . ? N13 C15 1.490(3) . ? C15 C16 1.529(3) . ? C15 C17 1.530(3) . ? C15 C18 1.530(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O19 C20 1.4399(19) . ? C20 C21 1.513(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N22 1.451(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N22 N26 1.351(2) . ? N22 C23 1.352(2) . ? C23 C24 1.358(3) . ? C23 H23A 0.9500 . ? C24 C25 1.402(3) . ? C24 H24A 0.9500 . ? C25 N26 1.339(2) . ? C25 C27 1.471(3) . ? C27 N28 1.345(3) . ? C27 C32 1.375(3) . ? N28 C29 1.329(4) . ? C29 C30 1.355(5) . ? C29 H29A 0.9500 . ? C30 C31 1.370(4) . ? C30 H30A 0.9500 . ? C31 C32 1.400(3) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? N33 C34 1.440(2) . ? N33 C40 1.445(2) . ? C34 C39 1.381(3) . ? C34 C35 1.393(3) . ? C35 C36 1.386(3) . ? C35 H35A 0.9500 . ? C36 C37 1.371(3) . ? C36 H36A 0.9500 . ? C37 C38 1.379(3) . ? C37 H37A 0.9500 . ? C38 C39 1.389(2) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? C40 C41 1.371(3) . ? C40 C45 1.380(3) . ? C41 C42 1.404(3) . ? C41 H41A 0.9500 . ? C42 C43 1.367(4) . ? C42 H42A 0.9500 . ? C43 C44 1.362(4) . ? C43 H43A 0.9500 . ? C44 C45 1.377(3) . ? C44 H44A 0.9500 . ? C45 H45A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 112.41(13) . . ? N3 C2 N7 117.92(14) . . ? N3 C2 N1 125.43(14) . . ? N7 C2 N1 116.64(14) . . ? C4 N3 C2 114.43(13) . . ? N3 C4 N5 126.08(14) . . ? N3 C4 N33 115.79(14) . . ? N5 C4 N33 118.12(14) . . ? C6 N5 C4 112.45(13) . . ? N1 C6 N5 129.19(15) . . ? N1 C6 O19 112.69(13) . . ? N5 C6 O19 118.09(14) . . ? C2 N7 C8 121.89(13) . . ? C2 N7 H7A 119.1 . . ? C8 N7 H7A 119.1 . . ? N7 C8 C9 111.03(13) . . ? N7 C8 C18 110.14(14) . . ? C9 C8 C18 109.15(15) . . ? N7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C18 C8 H8A 108.8 . . ? C8 C9 C10 112.84(14) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N13 C10 C12 108.74(14) . . ? N13 C10 C11 108.11(15) . . ? C12 C10 C11 109.58(16) . . ? N13 C10 C9 110.11(14) . . ? C12 C10 C9 111.37(14) . . ? C11 C10 C9 108.87(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O14 N13 C15 115.54(15) . . ? O14 N13 C10 115.25(15) . . ? C15 N13 C10 124.92(14) . . ? N13 C15 C16 109.54(16) . . ? N13 C15 C17 107.9(2) . . ? C16 C15 C17 109.2(2) . . ? N13 C15 C18 109.19(15) . . ? C16 C15 C18 111.03(17) . . ? C17 C15 C18 109.96(18) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 C15 113.18(15) . . ? C8 C18 H18A 108.9 . . ? C15 C18 H18A 108.9 . . ? C8 C18 H18B 108.9 . . ? C15 C18 H18B 108.9 . . ? H18A C18 H18B 107.8 . . ? C6 O19 C20 118.26(13) . . ? O19 C20 C21 112.22(14) . . ? O19 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? O19 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? N22 C21 C20 107.92(14) . . ? N22 C21 H21A 110.1 . . ? C20 C21 H21A 110.1 . . ? N22 C21 H21B 110.1 . . ? C20 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? N26 N22 C23 111.94(14) . . ? N26 N22 C21 120.03(15) . . ? C23 N22 C21 127.30(16) . . ? N22 C23 C24 107.33(17) . . ? N22 C23 H23A 126.3 . . ? C24 C23 H23A 126.3 . . ? C23 C24 C25 105.07(16) . . ? C23 C24 H24A 127.5 . . ? C25 C24 H24A 127.5 . . ? N26 C25 C24 111.16(16) . . ? N26 C25 C27 121.12(17) . . ? C24 C25 C27 127.72(17) . . ? C25 N26 N22 104.47(14) . . ? N28 C27 C32 122.5(2) . . ? N28 C27 C25 114.87(19) . . ? C32 C27 C25 122.66(18) . . ? C29 N28 C27 117.9(3) . . ? N28 C29 C30 123.8(3) . . ? N28 C29 H29A 118.1 . . ? C30 C29 H29A 118.1 . . ? C29 C30 C31 118.7(3) . . ? C29 C30 H30A 120.7 . . ? C31 C30 H30A 120.7 . . ? C30 C31 C32 119.3(3) . . ? C30 C31 H31A 120.3 . . ? C32 C31 H31A 120.3 . . ? C27 C32 C31 117.9(2) . . ? C27 C32 H32A 121.1 . . ? C31 C32 H32A 121.1 . . ? C4 N33 C34 124.28(14) . . ? C4 N33 C40 119.02(13) . . ? C34 N33 C40 116.56(13) . . ? C39 C34 C35 119.54(16) . . ? C39 C34 N33 122.12(15) . . ? C35 C34 N33 118.22(16) . . ? C36 C35 C34 119.81(19) . . ? C36 C35 H35A 120.1 . . ? C34 C35 H35A 120.1 . . ? C37 C36 C35 120.47(19) . . ? C37 C36 H36A 119.8 . . ? C35 C36 H36A 119.8 . . ? C36 C37 C38 119.92(19) . . ? C36 C37 H37A 120.0 . . ? C38 C37 H37A 120.0 . . ? C37 C38 C39 120.3(2) . . ? C37 C38 H38A 119.9 . . ? C39 C38 H38A 119.9 . . ? C34 C39 C38 119.98(18) . . ? C34 C39 H39A 120.0 . . ? C38 C39 H39A 120.0 . . ? C41 C40 C45 120.44(18) . . ? C41 C40 N33 119.75(16) . . ? C45 C40 N33 119.65(16) . . ? C40 C41 C42 119.0(2) . . ? C40 C41 H41A 120.5 . . ? C42 C41 H41A 120.5 . . ? C43 C42 C41 119.6(2) . . ? C43 C42 H42A 120.2 . . ? C41 C42 H42A 120.2 . . ? C44 C43 C42 121.2(2) . . ? C44 C43 H43A 119.4 . . ? C42 C43 H43A 119.4 . . ? C43 C44 C45 119.6(2) . . ? C43 C44 H44A 120.2 . . ? C45 C44 H44A 120.2 . . ? C44 C45 C40 120.1(2) . . ? C44 C45 H45A 119.9 . . ? C40 C45 H45A 119.9 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.294 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.053 # Attachment 'Compound_7b.CIF' data_7b _database_code_depnum_ccdc_archive 'CCDC 676756' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H38 N9 O3' _chemical_formula_weight 648.79 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4680(19) _cell_length_b 12.639(3) _cell_length_c 15.721(3) _cell_angle_alpha 106.96(3) _cell_angle_beta 95.71(3) _cell_angle_gamma 107.34(3) _cell_volume 1681.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20141 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 690 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14725 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0946 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7687 _reflns_number_gt 4215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non hydrogen atoms were refined anisotropically. All hydrogen atoms were fixed at calculated positions on their riding atom. The ethyl acetate solvent molecule is disordered (0.5:0.5 occupational factors) on two inverted positions as it sits close to the inversion center. Displacement and positional constrains were therefore used to model this molecule, and its hydrogen atoms were included in the model. ; _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^)+(0.0793P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7687 _refine_ls_number_parameters 460 _refine_ls_number_restraints 41 _refine_ls_R_factor_all 0.1285 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.0791(2) 0.89933(18) 0.02996(13) 0.0269(5) Uani 1 1 d . . . C2 C 0.1463(2) 0.8536(2) 0.08070(16) 0.0234(5) Uani 1 1 d . . . N3 N 0.1749(2) 0.75380(17) 0.05565(13) 0.0243(4) Uani 1 1 d . . . C4 C 0.1362(3) 0.6975(2) -0.03464(16) 0.0241(5) Uani 1 1 d . . . N5 N 0.0696(2) 0.73189(17) -0.09527(13) 0.0249(4) Uani 1 1 d . . . C6 C 0.0373(3) 0.8302(2) -0.05941(16) 0.0241(5) Uani 1 1 d . . . N7 N -0.0425(2) 0.86321(19) -0.11559(14) 0.0313(5) Uani 1 1 d . . . H7A H -0.0593 0.9299 -0.0941 0.038 Uiso 1 1 calc R . . C8 C -0.1024(3) 0.7922(2) -0.21141(16) 0.0290(6) Uani 1 1 d . . . H8A H -0.0839 0.7159 -0.2224 0.035 Uiso 1 1 calc R . . C9 C -0.2708(3) 0.7654(2) -0.23809(16) 0.0294(6) Uani 1 1 d . . . H9A H -0.2897 0.8400 -0.2314 0.035 Uiso 1 1 calc R . . H9B H -0.3223 0.7304 -0.1959 0.035 Uiso 1 1 calc R . . C10 C -0.3394(3) 0.6807(2) -0.33587(17) 0.0324(6) Uani 1 1 d . . . C11 C -0.4966(3) 0.6820(3) -0.3660(2) 0.0436(7) Uani 1 1 d . . . H11A H -0.5391 0.6279 -0.4285 0.065 Uiso 1 1 calc R . . H11B H -0.4898 0.7619 -0.3632 0.065 Uiso 1 1 calc R . . H11C H -0.5620 0.6571 -0.3258 0.065 Uiso 1 1 calc R . . C12 C -0.3515(4) 0.5537(3) -0.3449(2) 0.0468(8) Uani 1 1 d . . . H12A H -0.3950 0.5023 -0.4081 0.070 Uiso 1 1 calc R . . H12B H -0.4167 0.5265 -0.3053 0.070 Uiso 1 1 calc R . . H12C H -0.2507 0.5512 -0.3271 0.070 Uiso 1 1 calc R . . N13 N -0.2429(2) 0.72112(19) -0.39821(14) 0.0316(5) Uani 1 1 d . . . O14 O -0.3009(2) 0.67139(18) -0.48379(12) 0.0440(5) Uani 1 1 d . . . C15 C -0.0744(3) 0.7760(2) -0.37323(17) 0.0326(6) Uani 1 1 d . . . C16 C -0.0263(3) 0.8521(3) -0.4322(2) 0.0417(7) Uani 1 1 d . . . H16A H -0.0702 0.9147 -0.4190 0.063 Uiso 1 1 calc R . . H16B H -0.0620 0.8031 -0.4965 0.063 Uiso 1 1 calc R . . H16C H 0.0842 0.8872 -0.4190 0.063 Uiso 1 1 calc R . . C17 C -0.0057(3) 0.6763(3) -0.3942(2) 0.0451(8) Uani 1 1 d . . . H17A H -0.0364 0.6279 -0.3561 0.068 Uiso 1 1 calc R . . H17B H 0.1048 0.7110 -0.3814 0.068 Uiso 1 1 calc R . . H17C H -0.0421 0.6271 -0.4583 0.068 Uiso 1 1 calc R . . C18 C -0.0248(3) 0.8528(2) -0.27309(17) 0.0319(6) Uani 1 1 d . . . H18A H 0.0860 0.8746 -0.2545 0.038 Uiso 1 1 calc R . . H18B H -0.0471 0.9263 -0.2653 0.038 Uiso 1 1 calc R . . N19 N 0.1662(2) 0.59512(17) -0.06871(13) 0.0248(4) Uani 1 1 d . . . C20 C 0.2418(2) 0.5472(2) -0.01351(16) 0.0233(5) Uani 1 1 d . . . C21 C 0.3695(3) 0.6180(2) 0.05457(16) 0.0273(5) Uani 1 1 d . . . H21A H 0.4087 0.7005 0.0662 0.033 Uiso 1 1 calc R . . C22 C 0.4387(3) 0.5673(2) 0.10495(17) 0.0305(6) Uani 1 1 d . . . H22A H 0.5243 0.6155 0.1523 0.037 Uiso 1 1 calc R . . C23 C 0.3848(3) 0.4475(2) 0.08725(18) 0.0319(6) Uani 1 1 d . . . H23A H 0.4331 0.4136 0.1224 0.038 Uiso 1 1 calc R . . C24 C 0.2603(3) 0.3764(2) 0.01833(18) 0.0326(6) Uani 1 1 d . . . H24A H 0.2240 0.2936 0.0056 0.039 Uiso 1 1 calc R . . C25 C 0.1887(3) 0.4263(2) -0.03197(17) 0.0273(5) Uani 1 1 d . . . H25A H 0.1030 0.3776 -0.0791 0.033 Uiso 1 1 calc R . . C26 C 0.1067(3) 0.5264(2) -0.16362(16) 0.0241(5) Uani 1 1 d . . . C27 C -0.0470(3) 0.4669(2) -0.19462(16) 0.0277(5) Uani 1 1 d . . . H27A H -0.1141 0.4715 -0.1537 0.033 Uiso 1 1 calc R . . C28 C -0.1024(3) 0.4007(2) -0.28568(17) 0.0302(6) Uani 1 1 d . . . H28A H -0.2078 0.3597 -0.3074 0.036 Uiso 1 1 calc R . . C29 C -0.0038(3) 0.3938(2) -0.34546(17) 0.0326(6) Uani 1 1 d . . . H29A H -0.0422 0.3485 -0.4080 0.039 Uiso 1 1 calc R . . C30 C 0.1500(3) 0.4528(2) -0.31418(18) 0.0359(6) Uani 1 1 d . . . H30A H 0.2172 0.4478 -0.3550 0.043 Uiso 1 1 calc R . . C31 C 0.2056(3) 0.5191(2) -0.22288(17) 0.0300(6) Uani 1 1 d . . . H31A H 0.3111 0.5594 -0.2009 0.036 Uiso 1 1 calc R . . O32 O 0.18692(18) 0.91931(15) 0.16998(11) 0.0282(4) Uani 1 1 d . . . C33 C 0.2354(3) 0.8651(2) 0.23129(16) 0.0281(6) Uani 1 1 d . . . H33A H 0.2923 0.8152 0.2022 0.034 Uiso 1 1 calc R . . H33B H 0.1465 0.8147 0.2464 0.034 Uiso 1 1 calc R . . C34 C 0.3346(3) 0.9611(2) 0.31622(17) 0.0302(6) Uani 1 1 d . . . H34A H 0.4260 1.0093 0.3016 0.036 Uiso 1 1 calc R . . H34B H 0.2793 1.0131 0.3439 0.036 Uiso 1 1 calc R . . N35 N 0.3775(2) 0.90589(19) 0.37925(13) 0.0287(5) Uani 1 1 d . . . N36 N 0.2909(2) 0.8928(2) 0.44194(14) 0.0353(5) Uani 1 1 d . . . C37 C 0.3491(3) 0.8349(3) 0.48602(18) 0.0378(6) Uani 1 1 d . . . H37A H 0.3125 0.8139 0.5351 0.045 Uiso 1 1 calc R . . C38 C 0.4689(3) 0.8088(2) 0.45219(18) 0.0354(6) Uani 1 1 d . . . H38A H 0.5268 0.7677 0.4723 0.043 Uiso 1 1 calc R . . C39 C 0.4864(3) 0.8552(2) 0.38305(17) 0.0295(6) Uani 1 1 d . . . C40 C 0.5994(3) 0.8532(2) 0.32518(18) 0.0307(6) Uani 1 1 d . . . C41 C 0.7166(3) 0.8147(3) 0.3463(2) 0.0464(8) Uani 1 1 d . . . H41A H 0.7254 0.7916 0.3984 0.056 Uiso 1 1 calc R . . C42 C 0.8204(3) 0.8103(3) 0.2908(2) 0.0510(8) Uani 1 1 d . . . H42A H 0.9012 0.7840 0.3042 0.061 Uiso 1 1 calc R . . C43 C 0.8058(3) 0.8441(2) 0.2165(2) 0.0422(7) Uani 1 1 d . . . H43A H 0.8762 0.8422 0.1775 0.051 Uiso 1 1 calc R . . C44 C 0.6871(3) 0.8807(3) 0.1996(2) 0.0424(7) Uani 1 1 d . . . H44A H 0.6766 0.9031 0.1473 0.051 Uiso 1 1 calc R . . N45 N 0.5842(2) 0.8869(2) 0.25230(16) 0.0376(6) Uani 1 1 d . . . C46 C 0.537(2) 1.1197(12) 0.0814(11) 0.067(2) Uani 0.50 1 d PU . . O47 O 0.4809(7) 1.1735(6) 0.0501(5) 0.0869(19) Uani 0.50 1 d PU . . C48 C 0.6137(9) 1.1529(7) 0.1774(6) 0.0607(16) Uani 0.50 1 d PU . . O49 O 0.542(2) 1.0180(11) 0.0357(8) 0.076(2) Uani 0.50 1 d PU . . C50 C 0.461(4) 0.983(2) -0.0582(17) 0.115(5) Uani 0.50 1 d PDU . . C51 C 0.463(3) 0.8577(17) -0.1013(16) 0.127(5) Uani 0.50 1 d PDU . . 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 N1 0.0334(11) 0.0250(12) 0.0211(11) 0.0035(9) 0.0000(9) 0.0143(9) C2 0.0238(11) 0.0226(13) 0.0206(13) 0.0035(10) 0.0006(9) 0.0086(10) N3 0.0270(10) 0.0229(11) 0.0219(11) 0.0044(9) -0.0003(8) 0.0119(9) C4 0.0248(12) 0.0241(13) 0.0224(13) 0.0064(11) 0.0030(10) 0.0091(10) N5 0.0319(11) 0.0216(11) 0.0202(11) 0.0038(9) 0.0011(8) 0.0125(9) C6 0.0292(12) 0.0208(13) 0.0200(13) 0.0043(11) 0.0012(10) 0.0090(10) N7 0.0453(12) 0.0274(12) 0.0219(11) 0.0042(10) -0.0032(9) 0.0210(10) C8 0.0420(14) 0.0243(14) 0.0198(13) 0.0028(11) -0.0004(11) 0.0168(12) C9 0.0371(14) 0.0293(14) 0.0221(13) 0.0094(11) 0.0054(11) 0.0113(12) C10 0.0416(14) 0.0289(15) 0.0229(14) 0.0099(12) -0.0007(11) 0.0081(12) C11 0.0398(15) 0.0477(19) 0.0357(17) 0.0157(15) -0.0010(12) 0.0056(14) C12 0.069(2) 0.0300(17) 0.0325(17) 0.0093(14) -0.0042(14) 0.0101(15) N13 0.0422(12) 0.0332(13) 0.0182(11) 0.0072(10) 0.0006(9) 0.0147(10) O14 0.0584(12) 0.0504(13) 0.0188(10) 0.0071(9) -0.0029(9) 0.0206(11) C15 0.0390(14) 0.0362(16) 0.0268(14) 0.0086(12) 0.0068(11) 0.0208(12) C16 0.0485(17) 0.0477(19) 0.0368(17) 0.0177(15) 0.0157(13) 0.0221(15) C17 0.0600(19) 0.055(2) 0.0340(17) 0.0162(15) 0.0137(14) 0.0365(16) C18 0.0302(13) 0.0348(16) 0.0296(15) 0.0070(12) 0.0025(11) 0.0148(12) N19 0.0316(11) 0.0228(11) 0.0187(11) 0.0022(9) 0.0002(8) 0.0138(9) C20 0.0246(12) 0.0265(13) 0.0222(13) 0.0078(11) 0.0064(10) 0.0136(10) C21 0.0273(12) 0.0270(14) 0.0273(14) 0.0066(11) 0.0028(10) 0.0123(11) C22 0.0279(12) 0.0377(16) 0.0256(14) 0.0077(12) 0.0012(10) 0.0152(12) C23 0.0340(14) 0.0414(17) 0.0312(15) 0.0185(13) 0.0092(11) 0.0214(12) C24 0.0353(14) 0.0273(14) 0.0383(16) 0.0134(13) 0.0091(12) 0.0124(12) C25 0.0280(12) 0.0274(14) 0.0259(14) 0.0064(11) 0.0036(10) 0.0116(11) C26 0.0326(13) 0.0212(13) 0.0199(12) 0.0057(10) 0.0023(10) 0.0133(11) C27 0.0301(13) 0.0273(14) 0.0250(14) 0.0064(11) 0.0036(10) 0.0117(11) C28 0.0349(13) 0.0246(14) 0.0274(14) 0.0065(12) -0.0021(11) 0.0099(11) C29 0.0478(16) 0.0267(15) 0.0180(13) 0.0021(11) -0.0008(11) 0.0130(12) C30 0.0468(16) 0.0372(16) 0.0250(15) 0.0074(13) 0.0137(12) 0.0175(13) C31 0.0302(13) 0.0284(14) 0.0296(14) 0.0062(12) 0.0054(11) 0.0112(11) O32 0.0401(10) 0.0269(10) 0.0175(9) 0.0024(7) -0.0010(7) 0.0189(8) C33 0.0340(13) 0.0300(14) 0.0200(13) 0.0071(11) -0.0015(10) 0.0143(11) C34 0.0394(14) 0.0271(14) 0.0233(14) 0.0050(11) -0.0003(11) 0.0158(12) N35 0.0332(11) 0.0293(12) 0.0198(11) 0.0053(10) -0.0017(9) 0.0106(10) N36 0.0401(12) 0.0392(14) 0.0198(12) 0.0037(10) 0.0018(9) 0.0116(11) C37 0.0406(15) 0.0442(18) 0.0227(14) 0.0115(13) 0.0013(11) 0.0080(13) C38 0.0356(14) 0.0369(16) 0.0291(15) 0.0124(13) -0.0051(11) 0.0085(12) C39 0.0315(13) 0.0279(14) 0.0225(14) 0.0054(11) -0.0049(10) 0.0074(11) C40 0.0322(13) 0.0252(14) 0.0283(14) 0.0056(11) -0.0027(11) 0.0073(11) C41 0.0455(17) 0.053(2) 0.051(2) 0.0286(17) 0.0065(15) 0.0230(15) C42 0.0434(17) 0.053(2) 0.071(2) 0.0303(19) 0.0163(16) 0.0264(15) C43 0.0378(15) 0.0318(16) 0.053(2) 0.0097(15) 0.0159(14) 0.0093(13) C44 0.0418(16) 0.0462(19) 0.0369(17) 0.0166(15) 0.0090(13) 0.0093(14) N45 0.0360(12) 0.0433(15) 0.0346(13) 0.0181(12) 0.0039(10) 0.0114(11) C46 0.078(5) 0.063(4) 0.083(5) 0.046(4) 0.027(4) 0.031(4) O47 0.094(4) 0.086(4) 0.113(5) 0.063(4) 0.023(3) 0.047(3) C48 0.072(4) 0.062(4) 0.071(4) 0.038(4) 0.037(3) 0.035(3) O49 0.102(4) 0.063(3) 0.074(6) 0.039(3) 0.009(4) 0.031(3) C50 0.126(6) 0.105(6) 0.081(7) 0.026(6) 0.001(7) 0.004(6) C51 0.131(9) 0.102(8) 0.095(9) 0.004(6) 0.045(8) -0.013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.327(3) . ? N1 C6 1.364(3) . ? C2 N3 1.325(3) . ? C2 O32 1.353(3) . ? N3 C4 1.344(3) . ? C4 N5 1.334(3) . ? C4 N19 1.374(3) . ? N5 C6 1.345(3) . ? C6 N7 1.339(3) . ? N7 C8 1.461(3) . ? N7 H7A 0.8800 . ? C8 C9 1.515(3) . ? C8 C18 1.519(3) . ? C8 H8A 1.0000 . ? C9 C10 1.535(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N13 1.500(3) . ? C10 C11 1.523(4) . ? C10 C12 1.537(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N13 O14 1.289(3) . ? N13 C15 1.496(3) . ? C15 C18 1.527(4) . ? C15 C16 1.529(4) . ? C15 C17 1.551(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N19 C20 1.441(3) . ? N19 C26 1.443(3) . ? C20 C25 1.388(3) . ? C20 C21 1.395(3) . ? C21 C22 1.382(3) . ? C21 H21A 0.9500 . ? C22 C23 1.376(4) . ? C22 H22A 0.9500 . ? C23 C24 1.385(4) . ? C23 H23A 0.9500 . ? C24 C25 1.386(3) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 C27 1.383(3) . ? C26 C31 1.389(3) . ? C27 C28 1.384(3) . ? C27 H27A 0.9500 . ? C28 C29 1.392(3) . ? C28 H28A 0.9500 . ? C29 C30 1.383(4) . ? C29 H29A 0.9500 . ? C30 C31 1.387(4) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? O32 C33 1.447(3) . ? C33 C34 1.504(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 N35 1.458(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? N35 N36 1.359(3) . ? N35 C39 1.371(3) . ? N36 C37 1.334(3) . ? C37 C38 1.385(4) . ? C37 H37A 0.9500 . ? C38 C39 1.379(4) . ? C38 H38A 0.9500 . ? C39 C40 1.473(4) . ? C40 N45 1.343(3) . ? C40 C41 1.386(4) . ? C41 C42 1.380(4) . ? C41 H41A 0.9500 . ? C42 C43 1.364(4) . ? C42 H42A 0.9500 . ? C43 C44 1.368(4) . ? C43 H43A 0.9500 . ? C44 N45 1.345(3) . ? C44 H44A 0.9500 . ? C46 C51 0.36(3) 2_675 ? C46 O47 1.161(14) . ? C46 C50 1.24(3) 2_675 ? C46 O49 1.293(14) . ? C46 C48 1.487(19) . ? O47 C51 1.14(3) 2_675 ? C48 C51 1.29(3) 2_675 ? O49 C50 0.36(4) 2_675 ? O49 O49 1.19(3) 2_675 ? O49 C50 1.466(16) . ? O49 C51 1.63(2) 2_675 ? C50 O49 0.36(4) 2_675 ? C50 C46 1.24(3) 2_675 ? C50 C51 1.532(18) . ? C51 C46 0.36(3) 2_675 ? C51 O47 1.14(3) 2_675 ? C51 C48 1.29(3) 2_675 ? C51 O49 1.63(2) 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 C2 N1 C6 112.20(19) . . ? N3 C2 N1 128.9(2) . . ? N3 C2 O32 117.5(2) . . ? N1 C2 O32 113.58(19) . . ? C2 N3 C4 113.0(2) . . ? N5 C4 N3 125.7(2) . . ? N5 C4 N19 116.2(2) . . ? N3 C4 N19 118.1(2) . . ? C4 N5 C6 114.7(2) . . ? N7 C6 N5 117.7(2) . . ? N7 C6 N1 117.2(2) . . ? N5 C6 N1 125.2(2) . . ? C6 N7 C8 122.2(2) . . ? C6 N7 H7A 118.9 . . ? C8 N7 H7A 118.9 . . ? N7 C8 C9 112.2(2) . . ? N7 C8 C18 111.7(2) . . ? C9 C8 C18 108.0(2) . . ? N7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C18 C8 H8A 108.3 . . ? C8 C9 C10 113.2(2) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.8 . . ? N13 C10 C11 107.6(2) . . ? N13 C10 C9 109.2(2) . . ? C11 C10 C9 110.2(2) . . ? N13 C10 C12 109.4(2) . . ? C11 C10 C12 108.6(2) . . ? C9 C10 C12 111.7(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O14 N13 C15 116.1(2) . . ? O14 N13 C10 115.8(2) . . ? C15 N13 C10 124.0(2) . . ? N13 C15 C18 110.09(19) . . ? N13 C15 C16 107.4(2) . . ? C18 C15 C16 109.7(2) . . ? N13 C15 C17 108.5(2) . . ? C18 C15 C17 111.4(2) . . ? C16 C15 C17 109.7(2) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 C15 113.0(2) . . ? C8 C18 H18A 109.0 . . ? C15 C18 H18A 109.0 . . ? C8 C18 H18B 109.0 . . ? C15 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C4 N19 C20 123.7(2) . . ? C4 N19 C26 118.03(19) . . ? C20 N19 C26 118.05(18) . . ? C25 C20 C21 119.8(2) . . ? C25 C20 N19 118.3(2) . . ? C21 C20 N19 121.9(2) . . ? C22 C21 C20 119.5(2) . . ? C22 C21 H21A 120.2 . . ? C20 C21 H21A 120.2 . . ? C23 C22 C21 120.6(2) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C23 C24 C25 119.8(2) . . ? C23 C24 H24A 120.1 . . ? C25 C24 H24A 120.1 . . ? C24 C25 C20 120.1(2) . . ? C24 C25 H25A 120.0 . . ? C20 C25 H25A 120.0 . . ? C27 C26 C31 120.5(2) . . ? C27 C26 N19 120.2(2) . . ? C31 C26 N19 119.3(2) . . ? C26 C27 C28 119.5(2) . . ? C26 C27 H27A 120.2 . . ? C28 C27 H27A 120.2 . . ? C27 C28 C29 120.1(2) . . ? C27 C28 H28A 119.9 . . ? C29 C28 H28A 119.9 . . ? C30 C29 C28 120.2(2) . . ? C30 C29 H29A 119.9 . . ? C28 C29 H29A 119.9 . . ? C29 C30 C31 119.7(2) . . ? C29 C30 H30A 120.2 . . ? C31 C30 H30A 120.2 . . ? C30 C31 C26 119.9(2) . . ? C30 C31 H31A 120.1 . . ? C26 C31 H31A 120.1 . . ? C2 O32 C33 116.46(18) . . ? O32 C33 C34 108.41(19) . . ? O32 C33 H33A 110.0 . . ? C34 C33 H33A 110.0 . . ? O32 C33 H33B 110.0 . . ? C34 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? N35 C34 C33 108.1(2) . . ? N35 C34 H34A 110.1 . . ? C33 C34 H34A 110.1 . . ? N35 C34 H34B 110.1 . . ? C33 C34 H34B 110.1 . . ? H34A C34 H34B 108.4 . . ? N36 N35 C39 111.9(2) . . ? N36 N35 C34 117.0(2) . . ? C39 N35 C34 130.9(2) . . ? C37 N36 N35 104.3(2) . . ? N36 C37 C38 112.4(2) . . ? N36 C37 H37A 123.8 . . ? C38 C37 H37A 123.8 . . ? C39 C38 C37 105.4(2) . . ? C39 C38 H38A 127.3 . . ? C37 C38 H38A 127.3 . . ? N35 C39 C38 106.0(2) . . ? N35 C39 C40 126.3(2) . . ? C38 C39 C40 127.7(2) . . ? N45 C40 C41 121.8(2) . . ? N45 C40 C39 118.8(2) . . ? C41 C40 C39 119.3(2) . . ? C42 C41 C40 119.2(3) . . ? C42 C41 H41A 120.4 . . ? C40 C41 H41A 120.4 . . ? C43 C42 C41 119.4(3) . . ? C43 C42 H42A 120.3 . . ? C41 C42 H42A 120.3 . . ? C42 C43 C44 118.2(3) . . ? C42 C43 H43A 120.9 . . ? C44 C43 H43A 120.9 . . ? N45 C44 C43 124.1(3) . . ? N45 C44 H44A 117.9 . . ? C43 C44 H44A 117.9 . . ? C40 N45 C44 117.2(2) . . ? C51 C46 O47 78(6) 2_675 . ? C51 C46 C50 139(7) 2_675 2_675 ? O47 C46 C50 137(2) . 2_675 ? C51 C46 O49 156(6) 2_675 . ? O47 C46 O49 123.8(13) . . ? C51 C46 C48 50(6) 2_675 . ? O47 C46 C48 127.4(12) . . ? C50 C46 C48 95.2(17) 2_675 . ? O49 C46 C48 108.8(9) . . ? C51 C48 C50 49.3(10) 2_675 2_675 ? C50 O49 O49 136(10) 2_675 2_675 ? C50 O49 C46 74(5) 2_675 . ? O49 O49 C46 108.6(12) 2_675 . ? C50 O49 C50 146(8) 2_675 . ? C46 O49 C50 109.1(9) . . ? C50 O49 C51 69(5) 2_675 2_675 ? O49 O49 C51 112.6(17) 2_675 2_675 ? C50 O49 C51 113.6(12) . 2_675 ? O49 C50 C46 90(6) 2_675 2_675 ? C46 C50 O49 96(2) 2_675 . ? O49 C50 C51 99(5) 2_675 . ? O49 C50 C51 103.4(15) . . ? C46 C50 C50 95(2) 2_675 2_675 ? C51 C50 C50 103(2) . 2_675 ? O49 C50 C48 129(7) 2_675 2_675 ? C46 C50 C48 47.1(13) 2_675 2_675 ? O49 C50 C48 142.9(14) . 2_675 ? C50 C50 C48 142(2) 2_675 2_675 ? C46 C51 O47 84(6) 2_675 2_675 ? C46 C51 C48 117(7) 2_675 2_675 ? O47 C51 C48 156.1(18) 2_675 2_675 ? O47 C51 C50 112.3(16) 2_675 . ? C48 C51 C50 91.2(17) 2_675 . ? O47 C51 O49 101.5(17) 2_675 2_675 ? C48 C51 O49 101.3(18) 2_675 2_675 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.433 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.061 # Attachment 'Complex_8.CIF' data_zl50 _database_code_depnum_ccdc_archive 'CCDC 676757' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H90 Br5 Cu3 N22 O5' _chemical_formula_weight 1981.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 0.0020 '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 -0.0031 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O -0.0041 0.0074 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.1330 1.4803 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.8064 2.7887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.1172(15) _cell_length_b 17.1969(18) _cell_length_c 19.668(2) _cell_angle_alpha 70.009(2) _cell_angle_beta 77.210(3) _cell_angle_gamma 75.178(2) _cell_volume 4290.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.41 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2004 _exptl_absorpt_coefficient_mu 4.408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.63 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'ALS beamline 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Platinum 200 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 46705 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 29.05 _reflns_number_total 17521 _reflns_number_gt 11707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogens were refined anisotropically. Br atoms of the CuBr- ion and the acetonitrile molecules presented some disordered and required displacement parameters restrains, and in the latter case distance restrains. Hydrogens were found in difference Fourier maps and placed geometrically on their riding atom, except those of the coordinated water molecule that were refined with distance restrains. The data were cat at 0.8 angstroms as above I/sigma(I) < 2. ; _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^)+(0.0807P)^2^+19.1771P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 17521 _refine_ls_number_parameters 1010 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1037 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1896 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.83190(6) 0.72975(5) 0.34744(4) 0.03046(18) Uani 1 1 d . . . Cu2 Cu 0.42398(6) 0.66872(5) 0.29919(4) 0.0361(2) Uani 1 1 d . . . Cu3 Cu 0.67680(9) 0.61834(8) -0.25982(6) 0.0712(3) Uani 1 1 d U . . Br1 Br 0.82545(5) 0.86890(4) 0.26770(4) 0.03937(17) Uani 1 1 d . . . Br2 Br 1.03005(5) 0.69803(4) 0.33828(4) 0.03813(17) Uani 1 1 d . . . Br3 Br 0.30612(6) 0.78200(5) 0.32776(4) 0.04638(19) Uani 1 1 d . . . Br4 Br 0.67196(7) 0.61263(6) -0.36986(5) 0.0608(2) Uani 1 1 d U . . Br5 Br 0.68416(12) 0.62354(13) -0.15058(8) 0.1324(7) Uani 1 1 d U . . N1 N 0.5415(4) 0.8210(3) 0.1007(3) 0.0332(12) Uani 1 1 d . . . C2 C 0.5155(5) 0.7742(4) 0.1677(3) 0.0324(14) Uani 1 1 d . . . N3 N 0.4413(4) 0.7323(3) 0.1921(3) 0.0318(11) Uani 1 1 d . . . C4 C 0.3835(5) 0.7458(4) 0.1396(3) 0.0345(14) Uani 1 1 d . . . N5 N 0.4023(4) 0.7909(3) 0.0704(3) 0.0324(12) Uani 1 1 d . . . C6 C 0.4837(5) 0.8249(4) 0.0526(3) 0.0311(13) Uani 1 1 d . . . O7 O 0.5675(3) 0.7647(3) 0.2211(2) 0.0353(10) Uani 1 1 d . . . C8 C 0.6460(5) 0.8121(4) 0.2036(3) 0.0375(15) Uani 1 1 d . . . H8A H 0.6571 0.8192 0.2489 0.045 Uiso 1 1 calc R . . H8B H 0.6250 0.8690 0.1698 0.045 Uiso 1 1 calc R . . C9 C 0.7404(5) 0.7695(5) 0.1691(4) 0.0436(17) Uani 1 1 d . . . H9A H 0.7311 0.7672 0.1215 0.052 Uiso 1 1 calc R . . H9B H 0.7922 0.8029 0.1598 0.052 Uiso 1 1 calc R . . N10 N 0.7738(4) 0.6833(4) 0.2158(3) 0.0409(14) Uani 1 1 d . . . N11 N 0.7991(4) 0.6685(3) 0.2815(3) 0.0333(12) Uani 1 1 d . . . C12 C 0.8145(5) 0.5848(4) 0.3114(4) 0.0363(15) Uani 1 1 d . . . C13 C 0.7982(5) 0.5464(5) 0.2640(4) 0.0462(17) Uani 1 1 d . . . H13A H 0.8047 0.4878 0.2718 0.055 Uiso 1 1 calc R . . C14 C 0.7709(5) 0.6113(5) 0.2044(4) 0.0468(18) Uani 1 1 d . . . H14A H 0.7531 0.6065 0.1623 0.056 Uiso 1 1 calc R . . C15 C 0.8399(5) 0.5506(4) 0.3851(3) 0.0338(14) Uani 1 1 d . . . N16 N 0.8408(4) 0.6108(3) 0.4147(3) 0.0296(11) Uani 1 1 d . . . C17 C 0.8594(5) 0.5863(4) 0.4835(3) 0.0368(15) Uani 1 1 d . . . H17A H 0.8602 0.6283 0.5045 0.044 Uiso 1 1 calc R . . C18 C 0.8774(5) 0.5028(4) 0.5255(4) 0.0405(16) Uani 1 1 d . . . H18A H 0.8907 0.4875 0.5741 0.049 Uiso 1 1 calc R . . C19 C 0.8756(5) 0.4424(4) 0.4949(4) 0.0445(17) Uani 1 1 d . . . H19A H 0.8870 0.3844 0.5226 0.053 Uiso 1 1 calc R . . C20 C 0.8572(5) 0.4658(4) 0.4242(4) 0.0414(16) Uani 1 1 d . . . H20A H 0.8563 0.4244 0.4025 0.050 Uiso 1 1 calc R . . N21 N 0.3045(4) 0.7094(4) 0.1619(3) 0.0381(13) Uani 1 1 d . . . H21A H 0.2958 0.6776 0.2077 0.046 Uiso 1 1 calc R . . C22 C 0.2308(5) 0.7184(4) 0.1159(4) 0.0375(15) Uani 1 1 d . . . H22A H 0.2652 0.7165 0.0661 0.045 Uiso 1 1 calc R . . C23 C 0.1780(5) 0.6453(5) 0.1514(4) 0.0418(16) Uani 1 1 d . . . H23A H 0.1461 0.6469 0.2012 0.050 Uiso 1 1 calc R . . H23B H 0.2275 0.5920 0.1564 0.050 Uiso 1 1 calc R . . C24 C 0.0988(6) 0.6451(5) 0.1090(4) 0.0475(18) Uani 1 1 d . . . N25 N 0.0375(5) 0.7310(4) 0.0856(3) 0.0473(15) Uani 1 1 d . . . O26 O -0.0428(4) 0.7358(4) 0.0612(4) 0.0682(17) Uani 1 1 d . . . C27 C 0.0752(5) 0.8118(5) 0.0633(4) 0.0455(17) Uani 1 1 d . . . C28 C 0.1544(5) 0.7995(5) 0.1095(4) 0.0426(16) Uani 1 1 d . . . H28A H 0.1890 0.8477 0.0880 0.051 Uiso 1 1 calc R . . H28B H 0.1215 0.8006 0.1592 0.051 Uiso 1 1 calc R . . C29 C 0.0305(6) 0.5854(6) 0.1616(5) 0.064(2) Uani 1 1 d . . . H29A H 0.0004 0.6051 0.2042 0.096 Uiso 1 1 calc R . . H29B H 0.0696 0.5281 0.1777 0.096 Uiso 1 1 calc R . . H29C H -0.0216 0.5851 0.1361 0.096 Uiso 1 1 calc R . . C30 C 0.1454(7) 0.6153(6) 0.0430(5) 0.061(2) Uani 1 1 d . . . H30A H 0.1886 0.6533 0.0099 0.091 Uiso 1 1 calc R . . H30B H 0.0932 0.6152 0.0174 0.091 Uiso 1 1 calc R . . H30C H 0.1845 0.5580 0.0589 0.091 Uiso 1 1 calc R . . C31 C 0.1174(6) 0.8336(6) -0.0190(4) 0.055(2) Uani 1 1 d . . . H31A H 0.1740 0.7893 -0.0272 0.083 Uiso 1 1 calc R . . H31B H 0.1391 0.8877 -0.0350 0.083 Uiso 1 1 calc R . . H31C H 0.0660 0.8377 -0.0471 0.083 Uiso 1 1 calc R . . C32 C -0.0120(6) 0.8798(5) 0.0770(5) 0.058(2) Uani 1 1 d . . . H32A H -0.0387 0.8648 0.1292 0.087 Uiso 1 1 calc R . . H32B H -0.0635 0.8847 0.0487 0.087 Uiso 1 1 calc R . . H32C H 0.0097 0.9337 0.0620 0.087 Uiso 1 1 calc R . . N33 N 0.5093(4) 0.8678(3) -0.0182(3) 0.0327(12) Uani 1 1 d . . . C34 C 0.6003(5) 0.8985(4) -0.0450(3) 0.0332(14) Uani 1 1 d . . . C35 C 0.6898(5) 0.8449(5) -0.0297(4) 0.0437(17) Uani 1 1 d . . . H35A H 0.6918 0.7871 -0.0025 0.052 Uiso 1 1 calc R . . C36 C 0.7779(6) 0.8770(6) -0.0549(4) 0.053(2) Uani 1 1 d . . . H36A H 0.8392 0.8421 -0.0418 0.063 Uiso 1 1 calc R . . C37 C 0.7745(6) 0.9590(6) -0.0985(4) 0.054(2) Uani 1 1 d . . . H37A H 0.8341 0.9801 -0.1173 0.065 Uiso 1 1 calc R . . C38 C 0.6854(6) 1.0111(5) -0.1152(4) 0.0443(17) Uani 1 1 d . . . H38A H 0.6841 1.0678 -0.1452 0.053 Uiso 1 1 calc R . . C39 C 0.5973(5) 0.9813(4) -0.0884(3) 0.0367(15) Uani 1 1 d . . . H39A H 0.5360 1.0173 -0.0998 0.044 Uiso 1 1 calc R . . C40 C 0.4406(5) 0.8867(4) -0.0700(3) 0.0329(14) Uani 1 1 d . . . C41 C 0.4619(6) 0.8437(5) -0.1207(4) 0.0481(18) Uani 1 1 d . . . H41A H 0.5199 0.8012 -0.1216 0.058 Uiso 1 1 calc R . . C42 C 0.3970(6) 0.8637(6) -0.1706(4) 0.053(2) Uani 1 1 d . . . H42A H 0.4103 0.8338 -0.2055 0.064 Uiso 1 1 calc R . . C43 C 0.3150(6) 0.9251(6) -0.1703(4) 0.055(2) Uani 1 1 d . . . H43A H 0.2717 0.9384 -0.2051 0.066 Uiso 1 1 calc R . . C44 C 0.2936(6) 0.9693(5) -0.1191(4) 0.0458(17) Uani 1 1 d . . . H44A H 0.2360 1.0123 -0.1187 0.055 Uiso 1 1 calc R . . C45 C 0.3575(5) 0.9491(4) -0.0690(4) 0.0386(15) Uani 1 1 d . . . H45A H 0.3441 0.9785 -0.0338 0.046 Uiso 1 1 calc R . . N51 N 0.5987(4) 0.8247(3) 0.4915(3) 0.0325(11) Uani 1 1 d . . . C52 C 0.6595(5) 0.7929(4) 0.4423(3) 0.0292(13) Uani 1 1 d . . . N53 N 0.7587(4) 0.7767(3) 0.4327(3) 0.0294(11) Uani 1 1 d . . . C54 C 0.7971(4) 0.8003(4) 0.4780(3) 0.0311(13) Uani 1 1 d . . . N55 N 0.7440(4) 0.8340(3) 0.5297(3) 0.0326(12) Uani 1 1 d . . . C56 C 0.6454(5) 0.8453(4) 0.5337(3) 0.0319(13) Uani 1 1 d . . . O57 O 0.6237(3) 0.7725(3) 0.3946(2) 0.0363(10) Uani 1 1 d . . . C58 C 0.5165(5) 0.7887(5) 0.3979(4) 0.0464(18) Uani 1 1 d . . . H58A H 0.5002 0.7953 0.3496 0.056 Uiso 1 1 calc R . . H58B H 0.4864 0.8418 0.4102 0.056 Uiso 1 1 calc R . . C59 C 0.4744(6) 0.7159(6) 0.4556(4) 0.057(2) Uani 1 1 d . . . H59A H 0.4860 0.7131 0.5043 0.068 Uiso 1 1 calc R . . H59B H 0.4019 0.7272 0.4562 0.068 Uiso 1 1 calc R . . N60 N 0.5168(5) 0.6364(5) 0.4433(3) 0.0567(19) Uani 1 1 d . . . N61 N 0.5000(4) 0.6183(4) 0.3871(3) 0.0457(15) Uani 1 1 d . . . C62 C 0.5599(5) 0.5407(5) 0.3880(5) 0.056(2) Uani 1 1 d . . . C63 C 0.6124(6) 0.5112(7) 0.4464(5) 0.072(3) Uani 1 1 d . . . H63A H 0.6576 0.4590 0.4602 0.087 Uiso 1 1 calc R . . C64 C 0.5863(6) 0.5711(6) 0.4794(5) 0.060(2) Uani 1 1 d . . . H64A H 0.6113 0.5694 0.5210 0.072 Uiso 1 1 calc R . . C65 C 0.5581(6) 0.5069(5) 0.3316(5) 0.056(2) Uani 1 1 d . . . N66 N 0.4996(5) 0.5592(4) 0.2807(4) 0.0518(16) Uani 1 1 d . . . C67 C 0.4958(7) 0.5347(5) 0.2248(5) 0.059(2) Uani 1 1 d . . . H67A H 0.4549 0.5715 0.1897 0.071 Uiso 1 1 calc R . . C68 C 0.5478(8) 0.4589(6) 0.2141(6) 0.078(3) Uani 1 1 d . . . H68A H 0.5423 0.4432 0.1735 0.094 Uiso 1 1 calc R . . C69 C 0.6076(8) 0.4071(6) 0.2651(7) 0.086(3) Uani 1 1 d . . . H69A H 0.6455 0.3551 0.2589 0.103 Uiso 1 1 calc R . . C70 C 0.6136(7) 0.4284(6) 0.3235(6) 0.072(3) Uani 1 1 d . . . H70A H 0.6543 0.3915 0.3588 0.086 Uiso 1 1 calc R . . N71 N 0.8968(4) 0.7874(3) 0.4726(3) 0.0324(11) Uani 1 1 d . . . H71A H 0.9347 0.7742 0.4346 0.039 Uiso 1 1 calc R . . C72 C 0.9419(5) 0.7951(4) 0.5292(3) 0.0366(15) Uani 1 1 d . . . H72A H 0.9095 0.8492 0.5402 0.044 Uiso 1 1 calc R . . C73 C 1.0520(5) 0.7947(5) 0.5007(4) 0.0397(15) Uani 1 1 d . . . H73A H 1.0814 0.7438 0.4847 0.048 Uiso 1 1 calc R . . H73B H 1.0585 0.8447 0.4573 0.048 Uiso 1 1 calc R . . C74 C 1.1103(5) 0.7954(5) 0.5568(4) 0.0440(17) Uani 1 1 d . . . N75 N 1.0842(4) 0.7319(4) 0.6286(3) 0.0479(15) Uani 1 1 d . . . O76 O 1.1495(4) 0.7032(4) 0.6724(3) 0.0692(18) Uani 1 1 d . . . C77 C 0.9804(5) 0.7224(5) 0.6602(4) 0.0486(18) Uani 1 1 d . . . C78 C 0.9317(5) 0.7211(5) 0.5984(4) 0.0409(16) Uani 1 1 d . . . H78A H 0.9616 0.6680 0.5861 0.049 Uiso 1 1 calc R . . H78B H 0.8604 0.7211 0.6163 0.049 Uiso 1 1 calc R . . C79 C 1.0897(6) 0.8847(5) 0.5658(5) 0.058(2) Uani 1 1 d . . . H79A H 1.0188 0.9018 0.5817 0.086 Uiso 1 1 calc R . . H79B H 1.1099 0.9250 0.5190 0.086 Uiso 1 1 calc R . . H79C H 1.1273 0.8835 0.6026 0.086 Uiso 1 1 calc R . . C80 C 1.2212(5) 0.7680(6) 0.5313(4) 0.053(2) Uani 1 1 d . . . H80A H 1.2335 0.7117 0.5257 0.079 Uiso 1 1 calc R . . H80B H 1.2595 0.7667 0.5677 0.079 Uiso 1 1 calc R . . H80C H 1.2412 0.8082 0.4843 0.079 Uiso 1 1 calc R . . C81 C 0.9252(6) 0.7909(6) 0.6938(5) 0.060(2) Uani 1 1 d . . . H81A H 0.9232 0.8460 0.6563 0.090 Uiso 1 1 calc R . . H81B H 0.9590 0.7892 0.7330 0.090 Uiso 1 1 calc R . . H81C H 0.8575 0.7821 0.7141 0.090 Uiso 1 1 calc R . . N83 N 0.5906(4) 0.8800(3) 0.5854(3) 0.0333(12) Uani 1 1 d . . . C82 C 0.9837(6) 0.6364(6) 0.7199(4) 0.060(2) Uani 1 1 d . . . H82A H 1.0149 0.6363 0.7597 0.091 Uiso 1 1 calc R . . H82B H 1.0222 0.5917 0.6990 0.091 Uiso 1 1 calc R . . H82C H 0.9161 0.6266 0.7389 0.091 Uiso 1 1 calc R . . C84 C 0.4846(5) 0.8881(4) 0.6038(3) 0.0333(14) Uani 1 1 d . . . C85 C 0.4283(5) 0.9665(4) 0.6032(4) 0.0397(15) Uani 1 1 d . . . H85A H 0.4589 1.0142 0.5860 0.048 Uiso 1 1 calc R . . C86 C 0.3275(6) 0.9764(5) 0.6274(4) 0.0451(17) Uani 1 1 d . . . H86A H 0.2891 1.0308 0.6264 0.054 Uiso 1 1 calc R . . C87 C 0.2825(5) 0.9070(5) 0.6531(4) 0.0462(18) Uani 1 1 d . . . H87A H 0.2136 0.9130 0.6709 0.055 Uiso 1 1 calc R . . C88 C 0.3389(6) 0.8296(5) 0.6524(4) 0.0474(18) Uani 1 1 d . . . H88A H 0.3081 0.7820 0.6684 0.057 Uiso 1 1 calc R . . C89 C 0.4403(5) 0.8194(4) 0.6287(4) 0.0392(15) Uani 1 1 d . . . H89A H 0.4787 0.7650 0.6299 0.047 Uiso 1 1 calc R . . C90 C 0.6374(5) 0.9112(4) 0.6269(4) 0.0369(15) Uani 1 1 d . . . C91 C 0.6790(6) 0.9823(5) 0.5916(4) 0.0477(18) Uani 1 1 d . . . H91A H 0.6802 1.0083 0.5404 0.057 Uiso 1 1 calc R . . C92 C 0.7189(7) 1.0147(5) 0.6322(4) 0.056(2) Uani 1 1 d . . . H92A H 0.7475 1.0633 0.6090 0.067 Uiso 1 1 calc R . . C93 C 0.7166(6) 0.9756(6) 0.7072(5) 0.059(2) Uani 1 1 d . . . H93A H 0.7438 0.9975 0.7352 0.071 Uiso 1 1 calc R . . C94 C 0.6755(6) 0.9061(6) 0.7401(4) 0.056(2) Uani 1 1 d . . . H94A H 0.6737 0.8800 0.7913 0.068 Uiso 1 1 calc R . . C95 C 0.6360(5) 0.8723(5) 0.7000(4) 0.0440(17) Uani 1 1 d . . . H95A H 0.6084 0.8231 0.7234 0.053 Uiso 1 1 calc R . . O100 O 0.2870(4) 0.6001(3) 0.3216(3) 0.0432(12) Uani 1 1 d D . . H1W H 0.289(5) 0.554(3) 0.312(4) 0.052 Uiso 1 1 d D . . H2W H 0.225(2) 0.623(4) 0.334(4) 0.052 Uiso 1 1 d D . . N1S N 0.6344(7) 0.6354(5) 0.0623(5) 0.077(2) Uani 1 1 d DU . . C1S C 0.5718(9) 0.6252(7) 0.0407(6) 0.094(4) Uani 1 1 d DU . . C2S C 0.4889(11) 0.6094(9) 0.0106(8) 0.117(4) Uani 1 1 d DU . . H2S1 H 0.5184 0.5801 -0.0262 0.175 Uiso 1 1 calc R . . H2S2 H 0.4471 0.6634 -0.0117 0.175 Uiso 1 1 calc R . . H2S3 H 0.4485 0.5744 0.0507 0.175 Uiso 1 1 calc R . . N2S N 0.0330(10) 0.9222(8) 0.7727(8) 0.143(5) Uani 1 1 d DU . . C3S C -0.0065(8) 0.9901(7) 0.7492(7) 0.084(3) Uani 1 1 d DU . . C4S C -0.0587(9) 1.0735(7) 0.7252(7) 0.095(4) Uani 1 1 d DU . . H4S1 H -0.1296 1.0736 0.7316 0.142 Uiso 1 1 calc R . . H4S2 H -0.0350 1.0987 0.6733 0.142 Uiso 1 1 calc R . . H4S3 H -0.0480 1.1064 0.7538 0.142 Uiso 1 1 calc R . . C6S C 0.8704(12) 0.6169(10) -0.0241(8) 0.126(5) Uani 1 1 d DU . . H6S1 H 0.8036 0.6324 -0.0373 0.189 Uiso 1 1 calc R . . H6S2 H 0.9189 0.6057 -0.0655 0.189 Uiso 1 1 calc R . . H6S3 H 0.8841 0.6633 -0.0120 0.189 Uiso 1 1 calc R . . C5S C 0.8775(14) 0.5379(11) 0.0420(10) 0.141(6) Uani 1 1 d DU . . N3S N 0.8754(14) 0.4721(11) 0.0963(9) 0.172(6) Uani 1 1 d DU . . N4S N 0.6611(13) 0.3385(11) 0.1148(9) 0.163(6) Uani 1 1 d U . . C7S C 0.7456(12) 0.3095(11) 0.1402(8) 0.123(5) Uani 1 1 d DU . . C8S C 0.8454(11) 0.2767(10) 0.1651(8) 0.127(5) Uani 1 1 d DU . . H8S1 H 0.8846 0.3211 0.1450 0.191 Uiso 1 1 calc R . . H8S2 H 0.8797 0.2281 0.1479 0.191 Uiso 1 1 calc R . . H8S3 H 0.8370 0.2593 0.2187 0.191 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 0.0341(4) 0.0306(4) 0.0254(4) -0.0037(3) -0.0075(3) -0.0082(3) Cu2 0.0384(4) 0.0364(4) 0.0260(4) 0.0010(3) -0.0080(3) -0.0058(3) Cu3 0.0721(8) 0.0758(8) 0.0599(7) -0.0186(6) -0.0094(6) -0.0074(6) Br1 0.0422(4) 0.0357(4) 0.0343(3) 0.0011(3) -0.0117(3) -0.0084(3) Br2 0.0317(3) 0.0407(4) 0.0360(3) -0.0043(3) -0.0059(3) -0.0060(3) Br3 0.0408(4) 0.0535(4) 0.0516(4) -0.0236(4) -0.0138(3) -0.0042(3) Br4 0.0727(6) 0.0512(5) 0.0533(5) -0.0120(4) -0.0003(4) -0.0160(4) Br5 0.1192(12) 0.1964(18) 0.0779(8) -0.0634(10) -0.0345(8) 0.0227(11) N1 0.034(3) 0.038(3) 0.029(3) -0.005(2) -0.009(2) -0.011(2) C2 0.037(3) 0.035(3) 0.025(3) -0.005(3) -0.011(3) -0.007(3) N3 0.033(3) 0.033(3) 0.028(3) 0.001(2) -0.013(2) -0.011(2) C4 0.039(4) 0.032(3) 0.031(3) 0.000(3) -0.012(3) -0.012(3) N5 0.035(3) 0.037(3) 0.025(3) -0.001(2) -0.010(2) -0.014(2) C6 0.035(3) 0.032(3) 0.024(3) -0.004(2) -0.010(2) -0.005(3) O7 0.030(2) 0.046(3) 0.027(2) 0.0007(19) -0.0129(18) -0.011(2) C8 0.041(4) 0.048(4) 0.026(3) -0.005(3) -0.011(3) -0.016(3) C9 0.041(4) 0.058(5) 0.027(3) -0.001(3) -0.012(3) -0.012(3) N10 0.033(3) 0.060(4) 0.031(3) -0.016(3) -0.005(2) -0.009(3) N11 0.033(3) 0.041(3) 0.027(3) -0.007(2) -0.008(2) -0.010(2) C12 0.026(3) 0.046(4) 0.039(4) -0.016(3) -0.004(3) -0.007(3) C13 0.040(4) 0.054(5) 0.050(4) -0.023(4) -0.004(3) -0.010(3) C14 0.045(4) 0.067(5) 0.041(4) -0.030(4) -0.006(3) -0.015(4) C15 0.027(3) 0.043(4) 0.033(3) -0.011(3) -0.002(3) -0.011(3) N16 0.026(3) 0.035(3) 0.026(3) -0.006(2) -0.004(2) -0.010(2) C17 0.042(4) 0.039(4) 0.032(3) -0.007(3) -0.007(3) -0.015(3) C18 0.037(4) 0.041(4) 0.033(3) 0.003(3) -0.007(3) -0.006(3) C19 0.043(4) 0.033(4) 0.051(4) -0.008(3) -0.007(3) -0.004(3) C20 0.036(4) 0.035(4) 0.051(4) -0.014(3) -0.005(3) -0.005(3) N21 0.042(3) 0.042(3) 0.029(3) 0.002(2) -0.010(2) -0.021(3) C22 0.040(4) 0.049(4) 0.029(3) -0.010(3) -0.008(3) -0.019(3) C23 0.041(4) 0.048(4) 0.039(4) -0.009(3) -0.007(3) -0.019(3) C24 0.045(4) 0.051(4) 0.052(4) -0.013(4) -0.010(3) -0.019(4) N25 0.044(4) 0.057(4) 0.044(3) -0.008(3) -0.012(3) -0.019(3) O26 0.045(3) 0.084(4) 0.078(4) -0.011(3) -0.027(3) -0.019(3) C27 0.043(4) 0.052(4) 0.037(4) -0.003(3) -0.009(3) -0.014(3) C28 0.045(4) 0.048(4) 0.037(4) -0.007(3) -0.007(3) -0.020(3) C29 0.054(5) 0.071(6) 0.070(6) -0.004(5) -0.014(4) -0.037(5) C30 0.062(5) 0.072(6) 0.063(5) -0.029(5) -0.019(4) -0.019(5) C31 0.045(4) 0.076(6) 0.037(4) -0.006(4) -0.011(3) -0.009(4) C32 0.047(5) 0.060(5) 0.060(5) -0.007(4) -0.018(4) -0.007(4) N33 0.030(3) 0.043(3) 0.024(3) 0.000(2) -0.011(2) -0.012(2) C34 0.033(3) 0.040(4) 0.027(3) -0.007(3) -0.004(3) -0.011(3) C35 0.043(4) 0.044(4) 0.037(4) -0.001(3) -0.005(3) -0.011(3) C36 0.035(4) 0.072(6) 0.045(4) -0.005(4) -0.011(3) -0.012(4) C37 0.044(4) 0.084(6) 0.043(4) -0.021(4) 0.006(3) -0.035(4) C38 0.051(4) 0.050(4) 0.034(4) -0.011(3) 0.005(3) -0.025(4) C39 0.042(4) 0.041(4) 0.028(3) -0.009(3) -0.006(3) -0.013(3) C40 0.038(4) 0.040(4) 0.022(3) 0.000(3) -0.009(3) -0.018(3) C41 0.039(4) 0.064(5) 0.041(4) -0.017(4) -0.003(3) -0.012(4) C42 0.058(5) 0.076(6) 0.036(4) -0.021(4) -0.011(3) -0.021(4) C43 0.051(5) 0.079(6) 0.035(4) 0.000(4) -0.018(3) -0.027(4) C44 0.047(4) 0.049(4) 0.036(4) -0.001(3) -0.016(3) -0.008(3) C45 0.044(4) 0.041(4) 0.030(3) -0.002(3) -0.013(3) -0.014(3) N51 0.032(3) 0.037(3) 0.029(3) -0.007(2) -0.009(2) -0.008(2) C52 0.034(3) 0.025(3) 0.028(3) -0.004(2) -0.010(3) -0.004(2) N53 0.028(3) 0.033(3) 0.026(3) -0.006(2) -0.006(2) -0.006(2) C54 0.029(3) 0.032(3) 0.031(3) -0.005(3) -0.006(2) -0.006(3) N55 0.030(3) 0.034(3) 0.035(3) -0.009(2) -0.011(2) -0.006(2) C56 0.033(3) 0.030(3) 0.031(3) -0.005(3) -0.007(3) -0.008(3) O57 0.030(2) 0.050(3) 0.031(2) -0.014(2) -0.0058(18) -0.009(2) C58 0.036(4) 0.073(5) 0.039(4) -0.025(4) -0.013(3) -0.008(4) C59 0.041(4) 0.107(7) 0.031(4) -0.016(4) 0.000(3) -0.041(5) N60 0.047(4) 0.083(5) 0.033(3) 0.008(3) -0.009(3) -0.033(4) N61 0.038(3) 0.060(4) 0.030(3) 0.004(3) -0.004(2) -0.019(3) C62 0.027(4) 0.057(5) 0.056(5) 0.024(4) -0.012(3) -0.013(3) C63 0.039(5) 0.078(7) 0.067(6) 0.034(5) -0.018(4) -0.025(5) C64 0.045(5) 0.077(6) 0.044(4) 0.025(4) -0.025(4) -0.032(4) C65 0.042(4) 0.037(4) 0.059(5) 0.019(4) 0.000(4) -0.009(3) N66 0.046(4) 0.041(3) 0.050(4) 0.003(3) -0.002(3) -0.006(3) C67 0.070(6) 0.044(5) 0.052(5) -0.012(4) 0.002(4) -0.007(4) C68 0.092(8) 0.055(6) 0.074(6) -0.019(5) 0.012(6) -0.010(5) C69 0.080(7) 0.045(5) 0.099(8) -0.001(6) 0.015(6) -0.006(5) C70 0.054(5) 0.045(5) 0.091(7) 0.013(5) -0.011(5) -0.011(4) N71 0.029(3) 0.042(3) 0.028(3) -0.012(2) -0.006(2) -0.008(2) C72 0.034(3) 0.045(4) 0.036(3) -0.015(3) -0.011(3) -0.007(3) C73 0.035(4) 0.049(4) 0.035(3) -0.008(3) -0.008(3) -0.012(3) C74 0.036(4) 0.059(5) 0.040(4) -0.013(3) -0.007(3) -0.015(3) N75 0.039(3) 0.069(4) 0.033(3) -0.007(3) -0.013(3) -0.013(3) O76 0.049(3) 0.108(5) 0.051(3) -0.013(3) -0.025(3) -0.015(3) C77 0.035(4) 0.067(5) 0.039(4) -0.013(4) -0.001(3) -0.010(4) C78 0.037(4) 0.049(4) 0.036(4) -0.009(3) -0.007(3) -0.012(3) C79 0.054(5) 0.061(5) 0.070(5) -0.027(4) -0.008(4) -0.022(4) C80 0.032(4) 0.077(6) 0.045(4) -0.010(4) -0.006(3) -0.015(4) C81 0.054(5) 0.079(6) 0.051(5) -0.026(4) -0.008(4) -0.014(4) N83 0.035(3) 0.037(3) 0.032(3) -0.013(2) -0.006(2) -0.009(2) C82 0.057(5) 0.077(6) 0.035(4) -0.001(4) -0.009(4) -0.011(4) C84 0.036(3) 0.038(4) 0.027(3) -0.009(3) -0.008(3) -0.007(3) C85 0.038(4) 0.042(4) 0.036(4) -0.007(3) -0.009(3) -0.006(3) C86 0.050(4) 0.043(4) 0.040(4) -0.012(3) -0.012(3) 0.001(3) C87 0.033(4) 0.061(5) 0.042(4) -0.016(4) -0.011(3) 0.001(3) C88 0.047(4) 0.046(4) 0.051(4) -0.012(3) -0.003(3) -0.019(3) C89 0.040(4) 0.038(4) 0.042(4) -0.014(3) -0.008(3) -0.008(3) C90 0.033(3) 0.047(4) 0.036(3) -0.019(3) -0.004(3) -0.010(3) C91 0.060(5) 0.049(4) 0.039(4) -0.011(3) -0.007(3) -0.022(4) C92 0.070(6) 0.056(5) 0.052(5) -0.020(4) -0.005(4) -0.032(4) C93 0.057(5) 0.090(6) 0.052(5) -0.040(5) 0.003(4) -0.033(5) C94 0.061(5) 0.086(6) 0.033(4) -0.023(4) -0.002(3) -0.029(5) C95 0.046(4) 0.054(4) 0.034(4) -0.013(3) -0.003(3) -0.017(3) O100 0.037(3) 0.040(3) 0.055(3) -0.019(2) 0.009(2) -0.020(2) N1S 0.082(5) 0.069(5) 0.077(5) -0.001(4) -0.030(4) -0.024(4) C1S 0.109(7) 0.076(6) 0.079(6) -0.023(5) 0.015(6) -0.014(6) C2S 0.138(9) 0.121(8) 0.115(8) -0.063(7) -0.027(7) -0.021(7) N2S 0.129(8) 0.109(7) 0.170(9) -0.026(7) -0.011(7) -0.022(6) C3S 0.069(6) 0.077(6) 0.098(7) -0.015(5) 0.003(5) -0.029(5) C4S 0.085(6) 0.080(6) 0.113(7) 0.000(5) -0.033(6) -0.028(5) C6S 0.127(9) 0.127(8) 0.139(9) -0.051(7) -0.030(7) -0.025(7) C5S 0.150(10) 0.157(10) 0.146(9) -0.076(8) -0.036(8) -0.030(8) N3S 0.201(10) 0.181(10) 0.170(9) -0.094(8) -0.048(8) -0.023(8) N4S 0.169(9) 0.162(9) 0.169(9) -0.073(7) -0.011(7) -0.031(7) C7S 0.138(9) 0.134(9) 0.093(7) -0.048(7) -0.010(7) -0.009(7) C8S 0.134(9) 0.132(9) 0.109(8) -0.037(7) -0.021(7) -0.012(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N16 2.011(5) . ? Cu1 N53 2.066(5) . ? Cu1 N11 2.111(5) . ? Cu1 Br1 2.3621(10) . ? Cu1 Br2 2.6868(10) . ? Cu2 N3 2.007(5) . ? Cu2 N66 2.021(7) . ? Cu2 N61 2.052(6) . ? Cu2 Br3 2.3570(11) . ? Cu2 O100 2.400(4) . ? Cu3 Br5 2.2069(18) . ? Cu3 Br4 2.2163(15) . ? N1 C2 1.315(8) . ? N1 C6 1.356(8) . ? C2 N3 1.332(8) . ? C2 O7 1.354(7) . ? N3 C4 1.377(8) . ? C4 N5 1.322(8) . ? C4 N21 1.335(8) . ? N5 C6 1.346(8) . ? C6 N33 1.350(8) . ? O7 C8 1.453(8) . ? C8 C9 1.488(10) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N10 1.472(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N10 N11 1.340(7) . ? N10 C14 1.344(9) . ? N11 C12 1.336(9) . ? C12 C13 1.395(10) . ? C12 C15 1.456(9) . ? C13 C14 1.362(11) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 N16 1.352(8) . ? C15 C20 1.383(9) . ? N16 C17 1.338(8) . ? C17 C18 1.379(9) . ? C17 H17A 0.9500 . ? C18 C19 1.375(10) . ? C18 H18A 0.9500 . ? C19 C20 1.373(10) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? N21 C22 1.471(8) . ? N21 H21A 0.8800 . ? C22 C23 1.508(9) . ? C22 C28 1.515(10) . ? C22 H22A 1.0000 . ? C23 C24 1.536(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 N25 1.483(10) . ? C24 C30 1.512(11) . ? C24 C29 1.547(10) . ? N25 O26 1.300(8) . ? N25 C27 1.504(10) . ? C27 C32 1.512(11) . ? C27 C28 1.522(10) . ? C27 C31 1.545(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? N33 C34 1.437(8) . ? N33 C40 1.460(7) . ? C34 C39 1.383(9) . ? C34 C35 1.386(9) . ? C35 C36 1.410(10) . ? C35 H35A 0.9500 . ? C36 C37 1.372(12) . ? C36 H36A 0.9500 . ? C37 C38 1.377(11) . ? C37 H37A 0.9500 . ? C38 C39 1.393(9) . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? C40 C41 1.374(10) . ? C40 C45 1.374(10) . ? C41 C42 1.389(10) . ? C41 H41A 0.9500 . ? C42 C43 1.354(12) . ? C42 H42A 0.9500 . ? C43 C44 1.397(11) . ? C43 H43A 0.9500 . ? C44 C45 1.380(9) . ? C44 H44A 0.9500 . ? C45 H45A 0.9500 . ? N51 C52 1.314(8) . ? N51 C56 1.346(8) . ? C52 O57 1.336(7) . ? C52 N53 1.339(8) . ? N53 C54 1.350(8) . ? C54 N55 1.334(8) . ? C54 N71 1.353(8) . ? N55 C56 1.343(8) . ? C56 N83 1.349(8) . ? O57 C58 1.457(8) . ? C58 C59 1.524(11) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C59 N60 1.425(12) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? N60 N61 1.329(9) . ? N60 C64 1.388(10) . ? N61 C62 1.381(11) . ? C62 C63 1.383(12) . ? C62 C65 1.426(13) . ? C63 C64 1.333(14) . ? C63 H63A 0.9500 . ? C64 H64A 0.9500 . ? C65 N66 1.364(10) . ? C65 C70 1.418(13) . ? N66 C67 1.320(11) . ? C67 C68 1.383(12) . ? C67 H67A 0.9500 . ? C68 C69 1.375(16) . ? C68 H68A 0.9500 . ? C69 C70 1.344(15) . ? C69 H69A 0.9500 . ? C70 H70A 0.9500 . ? N71 C72 1.455(8) . ? N71 H71A 0.8800 . ? C72 C78 1.522(9) . ? C72 C73 1.530(9) . ? C72 H72A 1.0000 . ? C73 C74 1.521(9) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 N75 1.498(9) . ? C74 C80 1.536(10) . ? C74 C79 1.552(11) . ? N75 O76 1.290(7) . ? N75 C77 1.486(9) . ? C77 C81 1.505(12) . ? C77 C78 1.532(10) . ? C77 C82 1.539(11) . ? C78 H78A 0.9900 . ? C78 H78B 0.9900 . ? C79 H79A 0.9800 . ? C79 H79B 0.9800 . ? C79 H79C 0.9800 . ? C80 H80A 0.9800 . ? C80 H80B 0.9800 . ? C80 H80C 0.9800 . ? C81 H81A 0.9800 . ? C81 H81B 0.9800 . ? C81 H81C 0.9800 . ? N83 C84 1.441(8) . ? N83 C90 1.453(8) . ? C82 H82A 0.9800 . ? C82 H82B 0.9800 . ? C82 H82C 0.9800 . ? C84 C89 1.368(9) . ? C84 C85 1.377(9) . ? C85 C86 1.382(10) . ? C85 H85A 0.9500 . ? C86 C87 1.385(11) . ? C86 H86A 0.9500 . ? C87 C88 1.368(11) . ? C87 H87A 0.9500 . ? C88 C89 1.389(10) . ? C88 H88A 0.9500 . ? C89 H89A 0.9500 . ? C90 C95 1.361(9) . ? C90 C91 1.389(10) . ? C91 C92 1.389(10) . ? C91 H91A 0.9500 . ? C92 C93 1.392(11) . ? C92 H92A 0.9500 . ? C93 C94 1.358(12) . ? C93 H93A 0.9500 . ? C94 C95 1.394(10) . ? C94 H94A 0.9500 . ? C95 H95A 0.9500 . ? O100 H1W 0.87(6) . ? O100 H2W 0.88(5) . ? N1S C1S 1.135(12) . ? C1S C2S 1.541(14) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? N2S C3S 1.140(12) . ? C3S C4S 1.405(12) . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? C6S C5S 1.525(15) . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? C5S N3S 1.264(15) . ? N4S C7S 1.31(2) . ? C7S C8S 1.500(15) . ? C8S H8S1 0.9800 . ? C8S H8S2 0.9800 . ? C8S H8S3 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 N16 Cu1 N53 90.8(2) . . ? N16 Cu1 N11 78.5(2) . . ? N53 Cu1 N11 137.3(2) . . ? N16 Cu1 Br1 178.67(15) . . ? N53 Cu1 Br1 89.90(14) . . ? N11 Cu1 Br1 101.71(14) . . ? N16 Cu1 Br2 85.30(14) . . ? N53 Cu1 Br2 113.29(14) . . ? N11 Cu1 Br2 106.96(15) . . ? Br1 Cu1 Br2 93.39(3) . . ? N3 Cu2 N66 92.1(2) . . ? N3 Cu2 N61 141.4(2) . . ? N66 Cu2 N61 80.1(3) . . ? N3 Cu2 Br3 92.32(16) . . ? N66 Cu2 Br3 167.59(19) . . ? N61 Cu2 Br3 103.38(19) . . ? N3 Cu2 O100 106.47(19) . . ? N66 Cu2 O100 81.4(2) . . ? N61 Cu2 O100 109.5(2) . . ? Br3 Cu2 O100 86.27(12) . . ? Br5 Cu3 Br4 179.11(8) . . ? C2 N1 C6 113.5(5) . . ? N1 C2 N3 128.0(6) . . ? N1 C2 O7 119.4(5) . . ? N3 C2 O7 112.5(5) . . ? C2 N3 C4 113.2(5) . . ? C2 N3 Cu2 116.2(4) . . ? C4 N3 Cu2 130.3(4) . . ? N5 C4 N21 119.6(6) . . ? N5 C4 N3 124.4(6) . . ? N21 C4 N3 116.0(5) . . ? C4 N5 C6 115.6(5) . . ? N5 C6 N33 118.0(5) . . ? N5 C6 N1 124.9(5) . . ? N33 C6 N1 117.0(5) . . ? C2 O7 C8 118.5(5) . . ? O7 C8 C9 112.1(6) . . ? O7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? O7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N10 C9 C8 111.8(5) . . ? N10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? N10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? N11 N10 C14 111.4(6) . . ? N11 N10 C9 121.7(6) . . ? C14 N10 C9 126.3(6) . . ? C12 N11 N10 105.5(5) . . ? C12 N11 Cu1 112.3(4) . . ? N10 N11 Cu1 142.0(5) . . ? N11 C12 C13 110.5(6) . . ? N11 C12 C15 117.4(6) . . ? C13 C12 C15 132.0(7) . . ? C14 C13 C12 105.1(7) . . ? C14 C13 H13A 127.5 . . ? C12 C13 H13A 127.5 . . ? N10 C14 C13 107.5(6) . . ? N10 C14 H14A 126.3 . . ? C13 C14 H14A 126.3 . . ? N16 C15 C20 121.8(6) . . ? N16 C15 C12 113.4(6) . . ? C20 C15 C12 124.8(6) . . ? C17 N16 C15 118.2(6) . . ? C17 N16 Cu1 124.2(4) . . ? C15 N16 Cu1 117.1(4) . . ? N16 C17 C18 123.0(6) . . ? N16 C17 H17A 118.5 . . ? C18 C17 H17A 118.5 . . ? C19 C18 C17 118.1(6) . . ? C19 C18 H18A 121.0 . . ? C17 C18 H18A 121.0 . . ? C20 C19 C18 120.1(7) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C15 118.8(7) . . ? C19 C20 H20A 120.6 . . ? C15 C20 H20A 120.6 . . ? C4 N21 C22 125.0(5) . . ? C4 N21 H21A 117.5 . . ? C22 N21 H21A 117.5 . . ? N21 C22 C23 107.6(5) . . ? N21 C22 C28 112.3(6) . . ? C23 C22 C28 108.2(6) . . ? N21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? C28 C22 H22A 109.6 . . ? C22 C23 C24 113.9(6) . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23B 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? N25 C24 C30 109.8(7) . . ? N25 C24 C23 110.0(6) . . ? C30 C24 C23 111.3(7) . . ? N25 C24 C29 108.1(6) . . ? C30 C24 C29 109.8(7) . . ? C23 C24 C29 107.8(6) . . ? O26 N25 C24 115.5(6) . . ? O26 N25 C27 115.9(6) . . ? C24 N25 C27 124.9(6) . . ? N25 C27 C32 107.3(6) . . ? N25 C27 C28 108.6(6) . . ? C32 C27 C28 110.7(7) . . ? N25 C27 C31 108.5(6) . . ? C32 C27 C31 110.2(6) . . ? C28 C27 C31 111.3(6) . . ? C22 C28 C27 114.8(6) . . ? C22 C28 H28A 108.6 . . ? C27 C28 H28A 108.6 . . ? C22 C28 H28B 108.6 . . ? C27 C28 H28B 108.6 . . ? H28A C28 H28B 107.6 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C24 C30 H30A 109.5 . . ? C24 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C24 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C6 N33 C34 122.9(5) . . ? C6 N33 C40 119.2(5) . . ? C34 N33 C40 117.9(5) . . ? C39 C34 C35 120.7(6) . . ? C39 C34 N33 119.0(6) . . ? C35 C34 N33 120.3(6) . . ? C34 C35 C36 119.3(7) . . ? C34 C35 H35A 120.4 . . ? C36 C35 H35A 120.4 . . ? C37 C36 C35 119.6(7) . . ? C37 C36 H36A 120.2 . . ? C35 C36 H36A 120.2 . . ? C36 C37 C38 120.6(7) . . ? C36 C37 H37A 119.7 . . ? C38 C37 H37A 119.7 . . ? C37 C38 C39 120.5(7) . . ? C37 C38 H38A 119.7 . . ? C39 C38 H38A 119.7 . . ? C34 C39 C38 119.2(7) . . ? C34 C39 H39A 120.4 . . ? C38 C39 H39A 120.4 . . ? C41 C40 C45 120.9(6) . . ? C41 C40 N33 119.4(6) . . ? C45 C40 N33 119.6(6) . . ? C40 C41 C42 118.7(7) . . ? C40 C41 H41A 120.6 . . ? C42 C41 H41A 120.6 . . ? C43 C42 C41 120.8(7) . . ? C43 C42 H42A 119.6 . . ? C41 C42 H42A 119.6 . . ? C42 C43 C44 120.5(7) . . ? C42 C43 H43A 119.7 . . ? C44 C43 H43A 119.7 . . ? C45 C44 C43 118.8(7) . . ? C45 C44 H44A 120.6 . . ? C43 C44 H44A 120.6 . . ? C40 C45 C44 120.2(7) . . ? C40 C45 H45A 119.9 . . ? C44 C45 H45A 119.9 . . ? C52 N51 C56 113.4(5) . . ? N51 C52 O57 120.1(5) . . ? N51 C52 N53 127.5(5) . . ? O57 C52 N53 112.4(5) . . ? C52 N53 C54 113.7(5) . . ? C52 N53 Cu1 117.4(4) . . ? C54 N53 Cu1 128.6(4) . . ? N55 C54 N53 124.9(5) . . ? N55 C54 N71 116.4(5) . . ? N53 C54 N71 118.7(5) . . ? C54 N55 C56 114.7(5) . . ? N55 C56 N51 125.8(6) . . ? N55 C56 N83 115.4(5) . . ? N51 C56 N83 118.8(6) . . ? C52 O57 C58 118.1(5) . . ? O57 C58 C59 110.0(6) . . ? O57 C58 H58A 109.7 . . ? C59 C58 H58A 109.7 . . ? O57 C58 H58B 109.7 . . ? C59 C58 H58B 109.7 . . ? H58A C58 H58B 108.2 . . ? N60 C59 C58 113.1(6) . . ? N60 C59 H59A 108.9 . . ? C58 C59 H59A 108.9 . . ? N60 C59 H59B 108.9 . . ? C58 C59 H59B 108.9 . . ? H59A C59 H59B 107.8 . . ? N61 N60 C64 109.2(8) . . ? N61 N60 C59 121.7(6) . . ? C64 N60 C59 128.7(8) . . ? N60 N61 C62 105.9(6) . . ? N60 N61 Cu2 141.6(6) . . ? C62 N61 Cu2 112.3(5) . . ? N61 C62 C63 110.0(10) . . ? N61 C62 C65 117.6(6) . . ? C63 C62 C65 132.4(9) . . ? C64 C63 C62 105.6(9) . . ? C64 C63 H63A 127.2 . . ? C62 C63 H63A 127.2 . . ? C63 C64 N60 109.2(8) . . ? C63 C64 H64A 125.4 . . ? N60 C64 H64A 125.4 . . ? N66 C65 C70 120.1(9) . . ? N66 C65 C62 114.0(7) . . ? C70 C65 C62 125.9(8) . . ? C67 N66 C65 118.5(8) . . ? C67 N66 Cu2 125.5(6) . . ? C65 N66 Cu2 115.9(6) . . ? N66 C67 C68 124.2(9) . . ? N66 C67 H67A 117.9 . . ? C68 C67 H67A 117.9 . . ? C69 C68 C67 116.9(11) . . ? C69 C68 H68A 121.6 . . ? C67 C68 H68A 121.6 . . ? C70 C69 C68 121.6(10) . . ? C70 C69 H69A 119.2 . . ? C68 C69 H69A 119.2 . . ? C69 C70 C65 118.8(9) . . ? C69 C70 H70A 120.6 . . ? C65 C70 H70A 120.6 . . ? C54 N71 C72 120.7(5) . . ? C54 N71 H71A 119.7 . . ? C72 N71 H71A 119.7 . . ? N71 C72 C78 110.5(5) . . ? N71 C72 C73 108.1(5) . . ? C78 C72 C73 109.0(6) . . ? N71 C72 H72A 109.7 . . ? C78 C72 H72A 109.7 . . ? C73 C72 H72A 109.7 . . ? C74 C73 C72 113.7(6) . . ? C74 C73 H73A 108.8 . . ? C72 C73 H73A 108.8 . . ? C74 C73 H73B 108.8 . . ? C72 C73 H73B 108.8 . . ? H73A C73 H73B 107.7 . . ? N75 C74 C73 109.8(6) . . ? N75 C74 C80 107.0(6) . . ? C73 C74 C80 108.6(6) . . ? N75 C74 C79 110.4(6) . . ? C73 C74 C79 110.9(6) . . ? C80 C74 C79 110.0(6) . . ? O76 N75 C77 117.8(6) . . ? O76 N75 C74 116.5(6) . . ? C77 N75 C74 122.7(6) . . ? N75 C77 C81 112.2(7) . . ? N75 C77 C78 106.7(6) . . ? C81 C77 C78 112.5(6) . . ? N75 C77 C82 107.8(6) . . ? C81 C77 C82 108.9(7) . . ? C78 C77 C82 108.6(7) . . ? C72 C78 C77 114.1(6) . . ? C72 C78 H78A 108.7 . . ? C77 C78 H78A 108.7 . . ? C72 C78 H78B 108.7 . . ? C77 C78 H78B 108.7 . . ? H78A C78 H78B 107.6 . . ? C74 C79 H79A 109.5 . . ? C74 C79 H79B 109.5 . . ? H79A C79 H79B 109.5 . . ? C74 C79 H79C 109.5 . . ? H79A C79 H79C 109.5 . . ? H79B C79 H79C 109.5 . . ? C74 C80 H80A 109.5 . . ? C74 C80 H80B 109.5 . . ? H80A C80 H80B 109.5 . . ? C74 C80 H80C 109.5 . . ? H80A C80 H80C 109.5 . . ? H80B C80 H80C 109.5 . . ? C77 C81 H81A 109.5 . . ? C77 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? C77 C81 H81C 109.5 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? C56 N83 C84 123.5(5) . . ? C56 N83 C90 120.5(5) . . ? C84 N83 C90 115.9(5) . . ? C77 C82 H82A 109.5 . . ? C77 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C77 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C89 C84 C85 119.5(6) . . ? C89 C84 N83 122.0(6) . . ? C85 C84 N83 118.1(6) . . ? C84 C85 C86 120.6(7) . . ? C84 C85 H85A 119.7 . . ? C86 C85 H85A 119.7 . . ? C85 C86 C87 120.0(7) . . ? C85 C86 H86A 120.0 . . ? C87 C86 H86A 120.0 . . ? C88 C87 C86 118.9(7) . . ? C88 C87 H87A 120.5 . . ? C86 C87 H87A 120.5 . . ? C87 C88 C89 121.1(7) . . ? C87 C88 H88A 119.4 . . ? C89 C88 H88A 119.4 . . ? C84 C89 C88 119.8(7) . . ? C84 C89 H89A 120.1 . . ? C88 C89 H89A 120.1 . . ? C95 C90 C91 121.4(6) . . ? C95 C90 N83 119.4(6) . . ? C91 C90 N83 119.1(6) . . ? C90 C91 C92 119.0(7) . . ? C90 C91 H91A 120.5 . . ? C92 C91 H91A 120.5 . . ? C91 C92 C93 119.8(7) . . ? C91 C92 H92A 120.1 . . ? C93 C92 H92A 120.1 . . ? C94 C93 C92 119.8(7) . . ? C94 C93 H93A 120.1 . . ? C92 C93 H93A 120.1 . . ? C93 C94 C95 121.1(7) . . ? C93 C94 H94A 119.4 . . ? C95 C94 H94A 119.4 . . ? C90 C95 C94 118.9(7) . . ? C90 C95 H95A 120.6 . . ? C94 C95 H95A 120.6 . . ? Cu2 O100 H1W 126(4) . . ? Cu2 O100 H2W 124(4) . . ? H1W O100 H2W 109(4) . . ? N1S C1S C2S 178.3(13) . . ? C1S C2S H2S1 109.5 . . ? C1S C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? C1S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? N2S C3S C4S 176.0(15) . . ? C3S C4S H4S1 109.5 . . ? C3S C4S H4S2 109.5 . . ? H4S1 C4S H4S2 109.5 . . ? C3S C4S H4S3 109.5 . . ? H4S1 C4S H4S3 109.5 . . ? H4S2 C4S H4S3 109.5 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? N3S C5S C6S 175(2) . . ? N4S C7S C8S 176.9(16) . . ? C7S C8S H8S1 109.5 . . ? C7S C8S H8S2 109.5 . . ? H8S1 C8S H8S2 109.5 . . ? C7S C8S H8S3 109.5 . . ? H8S1 C8S H8S3 109.5 . . ? H8S2 C8S H8S3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.05 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.673 _refine_diff_density_min -1.337 _refine_diff_density_rms 0.116