# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jan Reedijk' _publ_contact_author_email REEDIJK@CHEM.LEIDENUNIV.NL _publ_section_title ; Selective, catalytic aerobic oxidation of alcohols using CuBr2 and bifunctional triazine-based ligands containing both a bipyridine and a TEMPO group ; loop_ _publ_author_name 'Jan Reedijk' 'Patrick Gamez' 'Zhengliang Lu' 'Chiara Massera' 'Olivier Roubeau' 'Simon J. Teat' ; J.v.d.Toorn ; # Attachment 'Compound_6.cif' data_zl69 _database_code_depnum_ccdc_archive 'CCDC 702598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C88 H103 Br4 Cu2 N23 O4' _chemical_formula_weight 1993.65 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 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0041 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Cu Cu 0.1330 1.4803 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Br Br -0.8064 2.7887 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _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 9.5728(8) _cell_length_b 10.7767(9) _cell_length_c 23.002(2) _cell_angle_alpha 87.355(2) _cell_angle_beta 84.576(2) _cell_angle_gamma 83.800(2) _cell_volume 2347.0(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7235 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 32.99 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1022 _exptl_absorpt_coefficient_mu 2.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.31 _exptl_absorpt_correction_T_max 0.90 _exptl_absorpt_process_details 'SADABS v2.10 Bruker AXS Madison WI US' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II 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 34487 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 33.70 _reflns_number_total 14014 _reflns_number_gt 10211 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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 atoms were refined anisotropical except for the disordered acetonitrile. Displacement parameter restrains were used in modelling the ligand and even with these a few atom have max:min ratios of more than the ideal of 3:1, the max is around 5.2:1. Splitting these atoms was considered but as no new chemical information would result they were left as they were reflecting the minot disorder in the ligand. The disordered acetonitriles were modelled using geometrical and displacement parameter restrains. Hydrogens were placed geometrically for the CH2, CH and aromatic carbons, the methyl hydrogens were found in the difference map along with the NH. All carbon hydrogens were then constrained and refined using a riding model. The NH hydrogen was allow to refine freely. ; _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^)+(0.0670P)^2^+0.0858P] 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 14014 _refine_ls_number_parameters 568 _refine_ls_number_restraints 170 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.066 _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 0.26177(3) 0.38068(3) 0.386466(13) 0.02218(8) Uani 1 1 d . . . Br1 Br 0.46328(3) 0.20181(3) 0.419985(12) 0.02911(8) Uani 1 1 d . . . Br2 Br 0.39152(3) 0.54965(3) 0.343231(13) 0.03226(8) Uani 1 1 d . . . N1 N 0.2290(2) 0.3406(2) 0.30328(9) 0.0238(4) Uani 1 1 d . . . C1 C 0.1173(3) 0.4057(2) 0.28160(11) 0.0229(5) Uani 1 1 d . . . N2 N 0.0882(2) 0.4168(2) 0.22658(9) 0.0257(5) Uani 1 1 d . . . C2 C 0.3227(3) 0.2835(2) 0.26122(11) 0.0237(5) Uani 1 1 d . . . N3 N 0.3061(2) 0.2909(2) 0.20397(10) 0.0255(5) Uani 1 1 d . . . C3 C 0.1889(3) 0.3584(2) 0.18919(11) 0.0240(5) Uani 1 1 d . . . N4 N 0.1691(3) 0.3698(2) 0.13107(10) 0.0290(5) Uani 1 1 d . . . C4 C 0.0536(3) 0.4516(3) 0.10940(12) 0.0299(6) Uani 1 1 d U . . C5 C 0.0328(4) 0.5754(3) 0.12268(14) 0.0443(8) Uani 1 1 d U . . H5 H 0.0944 0.6088 0.1465 0.053 Uiso 1 1 calc R . . C6 C -0.0787(5) 0.6522(4) 0.10125(15) 0.0580(10) Uani 1 1 d U . . H6 H -0.0944 0.7375 0.1112 0.070 Uiso 1 1 calc R . . C7 C -0.1668(4) 0.6045(4) 0.06544(16) 0.0577(11) Uani 1 1 d U . . H7 H -0.2429 0.6567 0.0507 0.069 Uiso 1 1 calc R . . C8 C -0.1433(4) 0.4816(4) 0.05157(15) 0.0535(9) Uani 1 1 d U . . H8 H -0.2032 0.4488 0.0268 0.064 Uiso 1 1 calc R . . C9 C -0.0335(4) 0.4040(3) 0.07317(13) 0.0417(7) Uani 1 1 d U . . H9 H -0.0180 0.3188 0.0632 0.050 Uiso 1 1 calc R . . C10 C 0.2724(3) 0.3099(3) 0.08891(12) 0.0331(6) Uani 1 1 d U . . C11 C 0.3760(4) 0.3736(4) 0.06230(15) 0.0488(9) Uani 1 1 d U . . H11 H 0.3812 0.4574 0.0724 0.059 Uiso 1 1 calc R . . C12 C 0.4757(4) 0.3189(5) 0.02024(17) 0.0604(11) Uani 1 1 d U . . H12 H 0.5488 0.3644 0.0024 0.072 Uiso 1 1 calc R . . C13 C 0.4668(4) 0.2000(4) 0.00522(17) 0.0566(10) Uani 1 1 d U . . H13 H 0.5328 0.1620 -0.0238 0.068 Uiso 1 1 calc R . . C14 C 0.3640(6) 0.1366(5) 0.0317(2) 0.0851(15) Uani 1 1 d U . . H14 H 0.3581 0.0532 0.0212 0.102 Uiso 1 1 calc R . . C15 C 0.2654(6) 0.1907(4) 0.0744(2) 0.0724(13) Uani 1 1 d U . . H15 H 0.1940 0.1440 0.0930 0.087 Uiso 1 1 calc R . . O1 O 0.0298(2) 0.4627(2) 0.32316(8) 0.0311(4) Uani 1 1 d U . . C16 C -0.1035(3) 0.5269(4) 0.30791(13) 0.0397(8) Uani 1 1 d U . . H16A H -0.1186 0.5110 0.2670 0.048 Uiso 1 1 calc R . . H16B H -0.1044 0.6181 0.3119 0.048 Uiso 1 1 calc R . . C17 C -0.2177(3) 0.4767(4) 0.34945(14) 0.0473(9) Uani 1 1 d U . . H17A H -0.3102 0.5117 0.3366 0.057 Uiso 1 1 calc R . . H17B H -0.2107 0.3851 0.3457 0.057 Uiso 1 1 calc R . . C18 C -0.2167(3) 0.5028(3) 0.41309(13) 0.0335(7) Uani 1 1 d U . . C19 C -0.3097(3) 0.4454(3) 0.45301(13) 0.0342(7) Uani 1 1 d . . . H19 H -0.3682 0.3883 0.4401 0.041 Uiso 1 1 calc R . . C20 C -0.3171(3) 0.4717(3) 0.51184(13) 0.0308(6) Uani 1 1 d . . . H20 H -0.3806 0.4312 0.5387 0.037 Uiso 1 1 calc R . . N5 N -0.2373(2) 0.5529(2) 0.53206(10) 0.0250(4) Uani 1 1 d . . . C21 C -0.1318(3) 0.5839(3) 0.43469(12) 0.0295(6) Uani 1 1 d . . . H21 H -0.0643 0.6224 0.4090 0.035 Uiso 1 1 calc R . . C22 C -0.1461(3) 0.6088(3) 0.49422(11) 0.0257(5) Uani 1 1 d . . . C23 C -0.0679(3) 0.7011(3) 0.51990(11) 0.0252(5) Uani 1 1 d . . . N6 N -0.1108(2) 0.7223(2) 0.57655(9) 0.0251(4) Uani 1 1 d . . . C24 C 0.0370(3) 0.7639(3) 0.48962(12) 0.0304(6) Uani 1 1 d . . . H24 H 0.0646 0.7471 0.4497 0.036 Uiso 1 1 calc R . . C25 C 0.1021(3) 0.8511(3) 0.51719(13) 0.0320(6) Uani 1 1 d . . . C26 C 0.0535(3) 0.8737(3) 0.57539(14) 0.0358(7) Uani 1 1 d . . . H26 H 0.0930 0.9340 0.5959 0.043 Uiso 1 1 calc R . . C27 C -0.0510(3) 0.8091(3) 0.60293(12) 0.0311(6) Uani 1 1 d . . . H27 H -0.0825 0.8264 0.6424 0.037 Uiso 1 1 calc R . . C28 C 0.2204(3) 0.9165(4) 0.48679(15) 0.0432(8) Uani 1 1 d . . . H28A H 0.3091 0.8848 0.5029 0.065 Uiso 1 1 calc R . . H28B H 0.2016 1.0065 0.4927 0.065 Uiso 1 1 calc R . . H28C H 0.2280 0.9012 0.4449 0.065 Uiso 1 1 calc R . . N7 N 0.4385(3) 0.2198(2) 0.27934(11) 0.0317(5) Uani 1 1 d . . . H7N H 0.448(4) 0.212(4) 0.3181(19) 0.060(12) Uiso 1 1 d . . . C29 C 0.5477(3) 0.1511(3) 0.24147(12) 0.0284(6) Uani 1 1 d . . . H29 H 0.5412 0.1826 0.2001 0.034 Uiso 1 1 calc R . . C30 C 0.6924(3) 0.1691(3) 0.26013(13) 0.0286(6) Uani 1 1 d . . . H30A H 0.7024 0.2596 0.2599 0.034 Uiso 1 1 calc R . . H30B H 0.6989 0.1355 0.3007 0.034 Uiso 1 1 calc R . . C31 C 0.8130(3) 0.1052(3) 0.22080(13) 0.0315(6) Uani 1 1 d . . . N8 N 0.7835(3) -0.0257(2) 0.21085(11) 0.0332(5) Uani 1 1 d . . . O2 O 0.8889(3) -0.0973(2) 0.18724(12) 0.0518(7) Uani 1 1 d . . . C32 C 0.6415(3) -0.0666(3) 0.20627(14) 0.0346(6) Uani 1 1 d . . . C33 C 0.5311(3) 0.0121(3) 0.24568(14) 0.0336(6) Uani 1 1 d . . . H33A H 0.4359 -0.0005 0.2351 0.040 Uiso 1 1 calc R . . H33B H 0.5378 -0.0182 0.2867 0.040 Uiso 1 1 calc R . . C34 C 0.6482(4) -0.2029(3) 0.22838(19) 0.0514(9) Uani 1 1 d . . . H34A H 0.7081 -0.2554 0.2003 0.077 Uiso 1 1 calc R . . H34B H 0.5529 -0.2295 0.2327 0.077 Uiso 1 1 calc R . . H34C H 0.6878 -0.2111 0.2663 0.077 Uiso 1 1 calc R . . C35 C 0.6070(4) -0.0539(4) 0.14275(16) 0.0495(9) Uani 1 1 d . . . H35A H 0.5883 0.0348 0.1315 0.074 Uiso 1 1 calc R . . H35B H 0.5234 -0.0964 0.1383 0.074 Uiso 1 1 calc R . . H35C H 0.6871 -0.0917 0.1176 0.074 Uiso 1 1 calc R . . C36 C 0.8338(4) 0.1760(4) 0.16145(15) 0.0482(9) Uani 1 1 d . . . H36A H 0.9079 0.1295 0.1363 0.072 Uiso 1 1 calc R . . H36B H 0.8614 0.2591 0.1675 0.072 Uiso 1 1 calc R . . H36C H 0.7453 0.1846 0.1427 0.072 Uiso 1 1 calc R . . C37 C 0.9488(3) 0.0979(3) 0.25116(16) 0.0402(7) Uani 1 1 d . . . H37A H 0.9402 0.0438 0.2865 0.060 Uiso 1 1 calc R . . H37B H 0.9650 0.1818 0.2619 0.060 Uiso 1 1 calc R . . H37C H 1.0282 0.0635 0.2246 0.060 Uiso 1 1 calc R . . N1S N 0.1826(4) 0.1375(3) 0.63595(15) 0.0545(8) Uani 1 1 d . . . C1S C 0.2948(4) 0.1441(3) 0.61446(15) 0.0413(7) Uani 1 1 d . . . C2S C 0.4371(4) 0.1539(4) 0.58786(16) 0.0463(8) Uani 1 1 d . . . H2S1 H 0.4333 0.1851 0.5473 0.069 Uiso 1 1 calc R . . H2S2 H 0.4913 0.0714 0.5887 0.069 Uiso 1 1 calc R . . H2S3 H 0.4827 0.2118 0.6097 0.069 Uiso 1 1 calc R . . N2S N 0.3939(5) 0.6503(4) 0.1452(2) 0.0793(12) Uani 1 1 d . . . C3S C 0.4744(5) 0.5787(4) 0.16394(18) 0.0547(10) Uani 1 1 d . . . N3S N 0.2280(5) -0.0671(4) 0.3305(2) 0.0835(13) Uani 1 1 d . . . C4S C 0.5791(5) 0.4866(4) 0.18708(18) 0.0532(9) Uani 1 1 d . . . H4S1 H 0.5733 0.4056 0.1703 0.080 Uiso 1 1 calc R . . H4S2 H 0.5611 0.4793 0.2297 0.080 Uiso 1 1 calc R . . H4S3 H 0.6735 0.5128 0.1769 0.080 Uiso 1 1 calc R . . C5S C 0.1912(4) -0.1396(4) 0.30209(18) 0.0530(9) Uani 1 1 d . . . C6S C 0.1476(5) -0.2286(4) 0.2639(3) 0.0796(16) Uani 1 1 d . . . H6S1 H 0.0479 -0.2070 0.2575 0.119 Uiso 1 1 calc R . . H6S2 H 0.1604 -0.3127 0.2819 0.119 Uiso 1 1 calc R . . H6S3 H 0.2050 -0.2262 0.2263 0.119 Uiso 1 1 calc R . . N4S N -0.0774(16) 0.0816(13) 0.0083(5) 0.062(3) Uiso 0.25 1 d PDU A 1 C7S C -0.1253(18) 0.1208(15) -0.0343(6) 0.060(3) Uiso 0.25 1 d PDU A 1 C8S C -0.1566(14) 0.1277(13) -0.0999(5) 0.032(2) Uiso 0.25 1 d PDU A 1 N4S' N -0.1776(16) 0.0991(14) -0.1188(6) 0.057(3) Uiso 0.25 1 d PDU B 2 C7S' C -0.150(2) 0.130(2) -0.0738(7) 0.075(4) Uiso 0.25 1 d PDU B 2 C8S' C -0.149(2) 0.149(2) -0.0070(6) 0.078(4) Uiso 0.25 1 d PDU B 2 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 0.02045(16) 0.02651(16) 0.01915(15) -0.00377(12) -0.00219(11) 0.00107(12) Br1 0.03015(15) 0.03045(14) 0.02591(14) -0.00171(10) -0.00768(11) 0.00529(11) Br2 0.03050(16) 0.03345(15) 0.03317(16) 0.00232(11) -0.00408(12) -0.00534(12) N1 0.0219(11) 0.0298(11) 0.0188(10) -0.0039(8) -0.0018(8) 0.0026(9) C1 0.0210(12) 0.0256(12) 0.0215(12) -0.0043(9) -0.0019(9) 0.0022(10) N2 0.0252(11) 0.0307(11) 0.0199(10) -0.0034(9) -0.0021(8) 0.0035(9) C2 0.0249(13) 0.0242(12) 0.0212(12) -0.0037(9) -0.0021(10) 0.0031(10) N3 0.0277(12) 0.0260(11) 0.0213(11) -0.0016(8) -0.0013(9) 0.0036(9) C3 0.0276(13) 0.0232(12) 0.0204(12) -0.0026(9) -0.0018(10) 0.0017(10) N4 0.0331(13) 0.0327(12) 0.0187(10) -0.0035(9) -0.0034(9) 0.0096(10) C4 0.0304(14) 0.0384(15) 0.0195(12) -0.0003(11) -0.0041(10) 0.0051(12) C5 0.061(2) 0.0390(17) 0.0314(15) -0.0090(13) -0.0168(15) 0.0172(15) C6 0.069(2) 0.062(2) 0.0349(17) -0.0068(16) -0.0096(16) 0.0360(19) C7 0.0413(19) 0.086(3) 0.0366(18) 0.0146(18) -0.0001(14) 0.0263(18) C8 0.0390(18) 0.089(3) 0.0342(17) 0.0184(17) -0.0133(14) -0.0143(18) C9 0.0487(19) 0.0518(19) 0.0265(15) 0.0077(13) -0.0091(13) -0.0126(15) C10 0.0359(16) 0.0384(15) 0.0222(13) -0.0058(11) -0.0021(11) 0.0112(12) C11 0.0415(19) 0.067(2) 0.0385(18) -0.0211(16) 0.0060(15) -0.0101(17) C12 0.041(2) 0.097(3) 0.044(2) -0.023(2) 0.0081(16) -0.011(2) C13 0.054(2) 0.068(2) 0.0407(18) -0.0152(17) 0.0046(16) 0.0250(18) C14 0.104(3) 0.056(2) 0.085(3) -0.026(2) 0.035(2) 0.010(2) C15 0.090(3) 0.0444(19) 0.075(2) -0.0159(18) 0.036(2) -0.0028(19) O1 0.0224(9) 0.0483(12) 0.0200(9) -0.0072(8) -0.0039(7) 0.0119(9) C16 0.0265(14) 0.066(2) 0.0226(13) -0.0111(13) -0.0068(11) 0.0191(14) C17 0.0244(15) 0.084(3) 0.0343(16) -0.0264(16) -0.0069(12) 0.0057(15) C18 0.0213(13) 0.0515(18) 0.0269(14) -0.0174(12) -0.0051(10) 0.0091(12) C19 0.0256(14) 0.0423(17) 0.0361(16) -0.0159(13) -0.0078(12) 0.0007(12) C20 0.0258(14) 0.0343(15) 0.0325(15) -0.0109(12) -0.0027(11) 0.0004(11) N5 0.0234(11) 0.0278(11) 0.0234(11) -0.0064(9) -0.0038(8) 0.0027(9) C21 0.0206(13) 0.0440(16) 0.0229(13) -0.0074(11) -0.0023(10) 0.0039(11) C22 0.0192(12) 0.0338(14) 0.0230(12) -0.0052(10) -0.0034(9) 0.0047(10) C23 0.0218(12) 0.0320(13) 0.0209(12) -0.0013(10) -0.0032(9) 0.0023(10) N6 0.0257(11) 0.0307(11) 0.0191(10) -0.0027(8) -0.0047(8) -0.0012(9) C24 0.0240(13) 0.0420(16) 0.0244(13) 0.0031(11) -0.0035(10) -0.0012(12) C25 0.0270(14) 0.0376(15) 0.0316(15) 0.0067(12) -0.0067(11) -0.0042(12) C26 0.0376(17) 0.0390(16) 0.0335(16) 0.0020(12) -0.0104(13) -0.0109(13) C27 0.0358(16) 0.0357(15) 0.0236(13) -0.0056(11) -0.0041(11) -0.0086(12) C28 0.0309(16) 0.057(2) 0.0429(19) 0.0126(16) -0.0074(14) -0.0133(15) N7 0.0307(13) 0.0407(14) 0.0200(11) -0.0032(10) -0.0020(9) 0.0135(10) C29 0.0265(14) 0.0309(14) 0.0253(13) -0.0050(10) -0.0017(10) 0.0088(11) C30 0.0267(14) 0.0267(13) 0.0314(14) -0.0068(11) -0.0011(11) 0.0029(11) C31 0.0287(14) 0.0312(14) 0.0330(15) -0.0012(11) -0.0005(11) 0.0019(11) N8 0.0274(12) 0.0343(13) 0.0358(13) -0.0118(10) -0.0039(10) 0.0110(10) O2 0.0356(13) 0.0538(15) 0.0634(17) -0.0294(13) -0.0046(12) 0.0190(11) C32 0.0310(15) 0.0330(15) 0.0401(17) -0.0127(12) -0.0077(12) 0.0036(12) C33 0.0269(14) 0.0336(15) 0.0403(17) -0.0060(12) -0.0051(12) 0.0010(12) C34 0.050(2) 0.0319(17) 0.073(3) -0.0142(17) -0.0125(19) 0.0015(15) C35 0.049(2) 0.057(2) 0.0431(19) -0.0209(17) -0.0145(16) 0.0103(17) C36 0.044(2) 0.057(2) 0.0388(19) 0.0056(16) 0.0075(15) 0.0055(17) C37 0.0277(15) 0.0441(18) 0.0492(19) -0.0076(15) -0.0057(14) -0.0017(13) N1S 0.051(2) 0.056(2) 0.057(2) -0.0018(16) 0.0009(16) -0.0123(16) C1S 0.053(2) 0.0334(16) 0.0384(18) -0.0020(13) -0.0069(15) -0.0054(15) C2S 0.048(2) 0.048(2) 0.0408(19) 0.0002(15) 0.0043(15) -0.0021(16) N2S 0.085(3) 0.074(3) 0.085(3) -0.020(2) -0.031(3) -0.007(2) C3S 0.064(3) 0.051(2) 0.052(2) -0.0171(18) -0.004(2) -0.013(2) N3S 0.070(3) 0.090(3) 0.092(3) -0.029(3) -0.020(2) 0.008(2) C4S 0.062(3) 0.0425(19) 0.053(2) -0.0028(17) 0.0070(19) -0.0067(18) C5S 0.039(2) 0.061(2) 0.055(2) -0.0004(19) -0.0024(17) 0.0072(18) C6S 0.068(3) 0.056(3) 0.118(4) -0.020(3) -0.043(3) 0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N6 2.018(2) 2_566 ? Cu1 N5 2.021(2) 2_566 ? Cu1 N1 2.041(2) . ? Cu1 Br2 2.4362(5) . ? Cu1 Br1 2.7152(4) . ? N1 C1 1.338(3) . ? N1 C2 1.375(3) . ? C1 N2 1.319(3) . ? C1 O1 1.336(3) . ? N2 C3 1.352(3) . ? C2 N7 1.331(3) . ? C2 N3 1.339(3) . ? N3 C3 1.333(3) . ? C3 N4 1.366(3) . ? N4 C10 1.440(3) . ? N4 C4 1.449(3) . ? C4 C5 1.372(4) . ? C4 C9 1.384(4) . ? C5 C6 1.392(5) . ? C5 H5 0.9500 . ? C6 C7 1.385(6) . ? C6 H6 0.9500 . ? C7 C8 1.367(6) . ? C7 H7 0.9500 . ? C8 C9 1.386(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.350(5) . ? C10 C15 1.353(5) . ? C11 C12 1.397(5) . ? C11 H11 0.9500 . ? C12 C13 1.355(6) . ? C12 H12 0.9500 . ? C13 C14 1.342(7) . ? C13 H13 0.9500 . ? C14 C15 1.397(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O1 C16 1.450(3) . ? C16 C17 1.511(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.504(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.390(5) . ? C18 C21 1.393(4) . ? C19 C20 1.389(4) . ? C19 H19 0.9500 . ? C20 N5 1.347(4) . ? C20 H20 0.9500 . ? N5 C22 1.344(4) . ? N5 Cu1 2.021(2) 2_566 ? C21 C22 1.399(4) . ? C21 H21 0.9500 . ? C22 C23 1.482(4) . ? C23 N6 1.351(3) . ? C23 C24 1.386(4) . ? N6 C27 1.343(3) . ? N6 Cu1 2.018(2) 2_566 ? C24 C25 1.389(4) . ? C24 H24 0.9500 . ? C25 C26 1.398(4) . ? C25 C28 1.499(4) . ? C26 C27 1.370(4) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? N7 C29 1.456(3) . ? N7 H7N 0.90(4) . ? C29 C33 1.521(4) . ? C29 C30 1.523(4) . ? C29 H29 1.0000 . ? C30 C31 1.522(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 N8 1.499(4) . ? C31 C37 1.525(4) . ? C31 C36 1.540(4) . ? N8 O2 1.294(3) . ? N8 C32 1.488(4) . ? C32 C35 1.525(5) . ? C32 C34 1.529(5) . ? C32 C33 1.534(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? N1S C1S 1.148(5) . ? C1S C2S 1.452(5) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? N2S C3S 1.131(6) . ? C3S C4S 1.453(6) . ? N3S C5S 1.145(6) . ? C4S H4S1 0.9800 . ? C4S H4S2 0.9800 . ? C4S H4S3 0.9800 . ? C5S C6S 1.449(6) . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? N4S C7S 1.162(5) . ? C7S C8S 1.562(5) . ? N4S' C7S' 1.163(5) . ? C7S' C8S' 1.561(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu1 N5 79.94(9) 2_566 2_566 ? N6 Cu1 N1 93.80(9) 2_566 . ? N5 Cu1 N1 163.21(9) 2_566 . ? N6 Cu1 Br2 164.51(7) 2_566 . ? N5 Cu1 Br2 95.06(7) 2_566 . ? N1 Cu1 Br2 86.88(7) . . ? N6 Cu1 Br1 89.88(7) 2_566 . ? N5 Cu1 Br1 90.06(6) 2_566 . ? N1 Cu1 Br1 105.59(6) . . ? Br2 Cu1 Br1 104.871(16) . . ? C1 N1 C2 113.4(2) . . ? C1 N1 Cu1 115.34(17) . . ? C2 N1 Cu1 128.71(18) . . ? N2 C1 O1 120.3(2) . . ? N2 C1 N1 127.5(2) . . ? O1 C1 N1 112.2(2) . . ? C1 N2 C3 113.7(2) . . ? N7 C2 N3 118.8(2) . . ? N7 C2 N1 116.8(2) . . ? N3 C2 N1 124.3(2) . . ? C3 N3 C2 115.2(2) . . ? N3 C3 N2 125.8(2) . . ? N3 C3 N4 117.0(2) . . ? N2 C3 N4 117.2(2) . . ? C3 N4 C10 120.0(2) . . ? C3 N4 C4 121.8(2) . . ? C10 N4 C4 117.9(2) . . ? C5 C4 C9 119.9(3) . . ? C5 C4 N4 121.0(3) . . ? C9 C4 N4 119.0(3) . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 119.4(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 121.0(4) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C4 C9 C8 119.6(4) . . ? C4 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C15 119.1(3) . . ? C11 C10 N4 120.1(3) . . ? C15 C10 N4 120.8(3) . . ? C10 C11 C12 121.4(4) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 119.3(4) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C12 119.4(4) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 121.3(4) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C10 C15 C14 119.5(4) . . ? C10 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C1 O1 C16 119.2(2) . . ? O1 C16 C17 107.0(3) . . ? O1 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? O1 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.6 . . ? C18 C17 C16 116.9(3) . . ? C18 C17 H17A 108.1 . . ? C16 C17 H17A 108.1 . . ? C18 C17 H17B 108.1 . . ? C16 C17 H17B 108.1 . . ? H17A C17 H17B 107.3 . . ? C19 C18 C21 117.5(3) . . ? C19 C18 C17 118.0(3) . . ? C21 C18 C17 124.4(3) . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N5 C20 C19 122.1(3) . . ? N5 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C22 N5 C20 118.9(2) . . ? C22 N5 Cu1 115.16(18) . 2_566 ? C20 N5 Cu1 125.3(2) . 2_566 ? C18 C21 C22 120.0(3) . . ? C18 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? N5 C22 C21 121.5(3) . . ? N5 C22 C23 115.1(2) . . ? C21 C22 C23 123.4(3) . . ? N6 C23 C24 121.8(3) . . ? N6 C23 C22 113.5(2) . . ? C24 C23 C22 124.7(2) . . ? C27 N6 C23 118.0(2) . . ? C27 N6 Cu1 126.05(19) . 2_566 ? C23 N6 Cu1 115.97(18) . 2_566 ? C23 C24 C25 120.4(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 116.7(3) . . ? C24 C25 C28 122.0(3) . . ? C26 C25 C28 121.2(3) . . ? C27 C26 C25 120.2(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? N6 C27 C26 122.9(3) . . ? N6 C27 H27 118.6 . . ? C26 C27 H27 118.6 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C2 N7 C29 124.6(2) . . ? C2 N7 H7N 119(3) . . ? C29 N7 H7N 116(3) . . ? N7 C29 C33 110.7(2) . . ? N7 C29 C30 109.7(2) . . ? C33 C29 C30 108.1(2) . . ? N7 C29 H29 109.5 . . ? C33 C29 H29 109.5 . . ? C30 C29 H29 109.5 . . ? C31 C30 C29 113.0(2) . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30B 109.0 . . ? C29 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? N8 C31 C30 109.5(2) . . ? N8 C31 C37 107.9(2) . . ? C30 C31 C37 109.2(3) . . ? N8 C31 C36 109.2(3) . . ? C30 C31 C36 111.7(3) . . ? C37 C31 C36 109.2(3) . . ? O2 N8 C32 115.6(2) . . ? O2 N8 C31 115.5(3) . . ? C32 N8 C31 125.5(2) . . ? N8 C32 C35 109.5(3) . . ? N8 C32 C34 106.6(3) . . ? C35 C32 C34 111.0(3) . . ? N8 C32 C33 109.5(2) . . ? C35 C32 C33 111.0(3) . . ? C34 C32 C33 109.1(3) . . ? C29 C33 C32 113.8(3) . . ? C29 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C29 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N1S C1S C2S 179.1(4) . . ? 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 179.1(5) . . ? 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 . . ? N3S C5S C6S 177.5(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 . . ? N4S C7S C8S 158.3(14) . . ? N4S' C7S' C8S' 163.2(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7N Br1 0.90(4) 2.36(4) 3.261(2) 177(4) . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.138 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.091 # Attachment 'Compound_7.CIF' data_zl52 _database_code_depnum_ccdc_archive 'CCDC 702599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C78 H88 Br4 Cu2 N18 O4' _chemical_formula_weight 1788.38 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 10.2403(4) _cell_length_b 13.9158(5) _cell_length_c 16.3583(6) _cell_angle_alpha 69.404(2) _cell_angle_beta 71.830(2) _cell_angle_gamma 75.030(3) _cell_volume 2044.14(13) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9867 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 33.92 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 3.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.40 _exptl_absorpt_correction_T_max 0.74 _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 28135 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0698 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 34.34 _reflns_number_total 12116 _reflns_number_gt 10202 _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. Hydrogens were found in difference Fourier maps, except for those of the lattice acetonitrile molecule, and were fixed at calculated positions on their riding atom. A number of C atoms showed Umax/Umin ratio superior to 3; no restrains were used though as these were close to 3 and it added no information. ; _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^)+(0.1187P)^2^+1.0151P] 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 12116 _refine_ls_number_parameters 479 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1869 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.29685(4) 0.81565(2) 0.44932(2) 0.02668(10) Uani 1 1 d . . . Br1 Br 0.12074(4) 0.70212(2) 0.47206(3) 0.04541(12) Uani 1 1 d . . . Br2 Br 0.45578(6) 0.67564(3) 0.51892(3) 0.0726(2) Uani 1 1 d . . . N1 N 0.4350(2) 0.82587(16) 0.31929(14) 0.0205(4) Uani 1 1 d . . . C2 C 0.4839(2) 0.91517(18) 0.27411(16) 0.0203(4) Uani 1 1 d . . . N3 N 0.5582(2) 0.94268(16) 0.18990(14) 0.0222(4) Uani 1 1 d . . . C4 C 0.5931(2) 0.86637(19) 0.15030(16) 0.0211(4) Uani 1 1 d . . . N5 N 0.5544(2) 0.77287(16) 0.18621(14) 0.0224(4) Uani 1 1 d . . . C6 C 0.4732(3) 0.75646(19) 0.27064(16) 0.0213(4) Uani 1 1 d . . . O7 O 0.45062(18) 0.98033(14) 0.32380(12) 0.0220(3) Uani 1 1 d . . . C8 C 0.4808(3) 1.08526(19) 0.27948(17) 0.0236(4) Uani 1 1 d . . . H8A H 0.4221 1.1309 0.3166 0.028 Uiso 1 1 calc R . . H8B H 0.4563 1.1119 0.2206 0.028 Uiso 1 1 calc R . . C9 C 0.6331(3) 1.0902(2) 0.26470(17) 0.0257(5) Uani 1 1 d . . . H9A H 0.6909 1.0480 0.2244 0.031 Uiso 1 1 calc R . . H9B H 0.6479 1.1632 0.2339 0.031 Uiso 1 1 calc R . . C10 C 0.6821(3) 1.0519(2) 0.35003(16) 0.0229(4) Uani 1 1 d . . . C11 C 0.6681(3) 1.1195(2) 0.39909(16) 0.0229(4) Uani 1 1 d . . . H11A H 0.6194 1.1883 0.3803 0.027 Uiso 1 1 calc R . . N12 N 0.7196(2) 1.09263(16) 0.47131(14) 0.0207(4) Uani 1 1 d . . . C13 C 0.7878(2) 0.99461(18) 0.49913(16) 0.0205(4) Uani 1 1 d . . . C14 C 0.8014(3) 0.9204(2) 0.45671(18) 0.0272(5) Uani 1 1 d . . . H14A H 0.8467 0.8511 0.4785 0.033 Uiso 1 1 calc R . . C15 C 0.7471(3) 0.9498(2) 0.38166(19) 0.0287(5) Uani 1 1 d . . . H15A H 0.7544 0.9002 0.3520 0.034 Uiso 1 1 calc R . . C16 C 0.8479(2) 0.97356(19) 0.57621(16) 0.0210(4) Uani 1 1 d . . . N17 N 0.8267(2) 1.05574(16) 0.60701(14) 0.0216(4) Uani 1 1 d . . . C18 C 0.8745(3) 1.0440(2) 0.67814(17) 0.0252(5) Uani 1 1 d . . . H18A H 0.8602 1.1027 0.6987 0.030 Uiso 1 1 calc R . . C19 C 0.9441(3) 0.9497(2) 0.72315(17) 0.0260(5) Uani 1 1 d . . . C20 C 0.9675(3) 0.8659(2) 0.68974(18) 0.0281(5) Uani 1 1 d . . . H20A H 1.0161 0.8005 0.7179 0.034 Uiso 1 1 calc R . . C21 C 0.9203(3) 0.8772(2) 0.61573(17) 0.0251(5) Uani 1 1 d . . . H21A H 0.9371 0.8205 0.5923 0.030 Uiso 1 1 calc R . . C22 C 0.9920(3) 0.9393(3) 0.80438(19) 0.0345(6) Uani 1 1 d . . . H22A H 1.0378 0.8675 0.8271 0.052 Uiso 1 1 calc R . . H22B H 0.9115 0.9565 0.8514 0.052 Uiso 1 1 calc R . . H22C H 1.0580 0.9870 0.7876 0.052 Uiso 1 1 calc R . . N23 N 0.4225(2) 0.66773(17) 0.30935(15) 0.0254(4) Uani 1 1 d . . . H23A H 0.3792 0.6525 0.3669 0.030 Uiso 1 1 calc R . . C24 C 0.4356(3) 0.59443(19) 0.26024(17) 0.0249(5) Uani 1 1 d . . . H24 H 0.4138 0.6342 0.2006 0.030 Uiso 1 1 calc R . . C25 C 0.3300(3) 0.5217(2) 0.3146(2) 0.0280(5) Uani 1 1 d . . . H25A H 0.2361 0.5638 0.3269 0.034 Uiso 1 1 calc R . . H25B H 0.3527 0.4814 0.3732 0.034 Uiso 1 1 calc R . . C26 C 0.3270(3) 0.4460(2) 0.2668(2) 0.0338(6) Uani 1 1 d . . . N27 N 0.4716(3) 0.39934(18) 0.22850(18) 0.0343(5) Uani 1 1 d . . . O28 O 0.4813(3) 0.32301(19) 0.1987(2) 0.0520(7) Uani 1 1 d . . . C29 C 0.5924(4) 0.4560(2) 0.1902(3) 0.0447(8) Uani 1 1 d . . . C30 C 0.5795(3) 0.5293(2) 0.2451(2) 0.0357(6) Uani 1 1 d . . . H30A H 0.5997 0.4875 0.3041 0.043 Uiso 1 1 calc R . . H30B H 0.6497 0.5761 0.2129 0.043 Uiso 1 1 calc R . . C31 C 0.2514(6) 0.5012(3) 0.1904(3) 0.0608(12) Uani 1 1 d . . . H31A H 0.2991 0.5581 0.1467 0.091 Uiso 1 1 calc R . . H31B H 0.1548 0.5294 0.2155 0.091 Uiso 1 1 calc R . . H31C H 0.2522 0.4512 0.1603 0.091 Uiso 1 1 calc R . . C32 C 0.2545(4) 0.3565(3) 0.3348(3) 0.0462(8) Uani 1 1 d . . . H32A H 0.3025 0.3223 0.3836 0.069 Uiso 1 1 calc R . . H32B H 0.2572 0.3060 0.3047 0.069 Uiso 1 1 calc R . . H32C H 0.1573 0.3836 0.3597 0.069 Uiso 1 1 calc R . . C33 C 0.7239(4) 0.3754(3) 0.1978(4) 0.0768(18) Uani 1 1 d . . . H33A H 0.7215 0.3393 0.2615 0.115 Uiso 1 1 calc R . . H33B H 0.8057 0.4102 0.1697 0.115 Uiso 1 1 calc R . . H33C H 0.7291 0.3249 0.1671 0.115 Uiso 1 1 calc R . . C34 C 0.5990(7) 0.5151(4) 0.0906(3) 0.0768(18) Uani 1 1 d . . . H34A H 0.6784 0.5525 0.0652 0.115 Uiso 1 1 calc R . . H34B H 0.5126 0.5650 0.0854 0.115 Uiso 1 1 calc R . . H34C H 0.6101 0.4656 0.0577 0.115 Uiso 1 1 calc R . . N35 N 0.6728(2) 0.88839(17) 0.06403(14) 0.0234(4) Uani 1 1 d . . . C36 C 0.7224(3) 0.9864(2) 0.02026(17) 0.0234(4) Uani 1 1 d . . . C37 C 0.6855(3) 1.0509(2) -0.0586(2) 0.0307(5) Uani 1 1 d . . . H37A H 0.6254 1.0315 -0.0819 0.037 Uiso 1 1 calc R . . C38 C 0.7372(3) 1.1444(2) -0.1036(2) 0.0366(6) Uani 1 1 d . . . H38A H 0.7131 1.1882 -0.1581 0.044 Uiso 1 1 calc R . . C39 C 0.8236(3) 1.1732(2) -0.0689(2) 0.0363(6) Uani 1 1 d . . . H39A H 0.8576 1.2372 -0.0988 0.044 Uiso 1 1 calc R . . C40 C 0.8602(3) 1.1079(3) 0.0099(2) 0.0347(6) Uani 1 1 d . . . H40A H 0.9191 1.1277 0.0339 0.042 Uiso 1 1 calc R . . C41 C 0.8113(3) 1.0140(2) 0.05397(18) 0.0302(5) Uani 1 1 d . . . H41A H 0.8387 0.9687 0.1070 0.036 Uiso 1 1 calc R . . C42 C 0.7314(3) 0.8086(2) 0.01940(17) 0.0252(5) Uani 1 1 d . . . C43 C 0.6708(3) 0.8028(2) -0.04379(19) 0.0305(5) Uani 1 1 d . . . H43A H 0.5856 0.8467 -0.0535 0.037 Uiso 1 1 calc R . . C44 C 0.7369(4) 0.7317(3) -0.0925(2) 0.0374(6) Uani 1 1 d . . . H44A H 0.6962 0.7266 -0.1353 0.045 Uiso 1 1 calc R . . C45 C 0.8616(4) 0.6684(3) -0.0786(2) 0.0378(7) Uani 1 1 d . . . H45A H 0.9078 0.6217 -0.1133 0.045 Uiso 1 1 calc R . . C46 C 0.9196(3) 0.6729(3) -0.0138(2) 0.0378(6) Uani 1 1 d . . . H46A H 1.0041 0.6282 -0.0034 0.045 Uiso 1 1 calc R . . C47 C 0.8538(3) 0.7430(2) 0.0358(2) 0.0318(5) Uani 1 1 d . . . H47A H 0.8925 0.7459 0.0805 0.038 Uiso 1 1 calc R . . N1S N -0.1385(6) 0.7589(4) 0.2523(3) 0.0818(14) Uani 1 1 d . . . C1S C -0.1500(6) 0.6881(5) 0.3141(4) 0.0709(13) Uani 1 1 d . . . C2S C -0.1644(9) 0.5993(6) 0.3961(5) 0.114(3) Uani 1 1 d . . . H2S1 H -0.1014 0.5976 0.4312 0.170 Uiso 1 1 calc R . . H2S2 H -0.1408 0.5345 0.3796 0.170 Uiso 1 1 calc R . . H2S3 H -0.2608 0.6063 0.4323 0.170 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 0.0387(2) 0.02160(16) 0.01907(16) -0.00936(11) -0.00926(13) 0.00347(12) Br1 0.04144(19) 0.02736(17) 0.0580(2) -0.02076(14) 0.01748(15) -0.01492(13) Br2 0.1187(4) 0.0537(2) 0.0453(2) -0.03355(19) -0.0529(3) 0.0526(3) N1 0.0243(9) 0.0199(9) 0.0197(9) -0.0096(7) -0.0022(7) -0.0067(7) C2 0.0226(10) 0.0208(10) 0.0210(10) -0.0099(8) -0.0049(8) -0.0044(8) N3 0.0276(10) 0.0217(9) 0.0194(9) -0.0077(7) -0.0025(7) -0.0090(7) C4 0.0230(10) 0.0225(10) 0.0194(10) -0.0088(8) -0.0028(8) -0.0054(8) N5 0.0276(10) 0.0213(9) 0.0198(9) -0.0090(7) -0.0011(7) -0.0081(7) C6 0.0247(10) 0.0204(10) 0.0214(10) -0.0089(8) -0.0038(8) -0.0065(8) O7 0.0262(8) 0.0214(8) 0.0219(8) -0.0121(6) -0.0012(6) -0.0078(6) C8 0.0289(11) 0.0186(10) 0.0270(11) -0.0097(8) -0.0065(9) -0.0067(8) C9 0.0301(12) 0.0307(12) 0.0210(11) -0.0091(9) -0.0039(9) -0.0136(10) C10 0.0245(10) 0.0267(11) 0.0203(10) -0.0093(8) -0.0015(8) -0.0107(9) C11 0.0255(11) 0.0237(11) 0.0215(10) -0.0107(8) -0.0048(8) -0.0032(8) N12 0.0242(9) 0.0198(9) 0.0186(9) -0.0067(7) -0.0036(7) -0.0048(7) C13 0.0212(10) 0.0197(10) 0.0200(10) -0.0064(8) -0.0023(8) -0.0052(8) C14 0.0347(13) 0.0205(11) 0.0282(12) -0.0095(9) -0.0077(10) -0.0046(9) C15 0.0347(13) 0.0261(12) 0.0302(13) -0.0136(10) -0.0060(10) -0.0082(10) C16 0.0210(10) 0.0215(10) 0.0194(10) -0.0062(8) -0.0016(8) -0.0053(8) N17 0.0224(9) 0.0211(9) 0.0209(9) -0.0070(7) -0.0030(7) -0.0044(7) C18 0.0262(11) 0.0286(12) 0.0214(11) -0.0074(9) -0.0046(9) -0.0073(9) C19 0.0216(10) 0.0335(13) 0.0206(11) -0.0026(9) -0.0041(8) -0.0093(9) C20 0.0242(11) 0.0281(12) 0.0250(12) -0.0024(9) -0.0049(9) -0.0019(9) C21 0.0244(11) 0.0221(11) 0.0246(11) -0.0054(9) -0.0025(9) -0.0034(8) C22 0.0299(13) 0.0489(17) 0.0225(12) -0.0047(11) -0.0086(10) -0.0082(12) N23 0.0357(11) 0.0216(9) 0.0210(9) -0.0122(8) 0.0025(8) -0.0118(8) C24 0.0357(13) 0.0192(10) 0.0201(10) -0.0087(8) -0.0004(9) -0.0087(9) C25 0.0297(12) 0.0217(11) 0.0343(13) -0.0132(10) -0.0015(10) -0.0080(9) C26 0.0391(14) 0.0233(12) 0.0442(16) -0.0156(11) -0.0085(12) -0.0084(10) N27 0.0439(13) 0.0186(10) 0.0374(13) -0.0133(9) 0.0048(10) -0.0111(9) O28 0.0725(18) 0.0274(11) 0.0576(16) -0.0275(11) 0.0061(13) -0.0169(11) C29 0.0499(18) 0.0258(13) 0.0495(19) -0.0190(13) 0.0182(14) -0.0173(13) C30 0.0333(14) 0.0239(12) 0.0456(17) -0.0147(11) 0.0056(12) -0.0098(10) C31 0.090(3) 0.0412(19) 0.076(3) -0.0240(19) -0.052(3) -0.003(2) C32 0.0409(17) 0.0346(16) 0.065(2) -0.0235(16) 0.0044(15) -0.0189(13) C33 0.0403(19) 0.041(2) 0.132(5) -0.044(3) 0.028(2) -0.0139(16) C34 0.134(5) 0.045(2) 0.039(2) -0.0237(17) 0.031(2) -0.043(3) N35 0.0305(10) 0.0231(9) 0.0185(9) -0.0100(7) 0.0007(7) -0.0104(8) C36 0.0256(11) 0.0237(11) 0.0211(10) -0.0082(8) -0.0007(8) -0.0086(9) C37 0.0318(13) 0.0299(13) 0.0322(13) -0.0056(10) -0.0117(10) -0.0083(10) C38 0.0408(15) 0.0302(14) 0.0355(15) 0.0022(11) -0.0152(12) -0.0100(12) C39 0.0429(16) 0.0279(13) 0.0381(15) -0.0048(11) -0.0093(12) -0.0134(12) C40 0.0420(15) 0.0374(15) 0.0305(13) -0.0079(11) -0.0074(11) -0.0210(12) C41 0.0366(14) 0.0326(13) 0.0232(12) -0.0060(10) -0.0053(10) -0.0145(11) C42 0.0300(12) 0.0252(11) 0.0206(10) -0.0106(9) 0.0027(9) -0.0105(9) C43 0.0379(14) 0.0309(13) 0.0260(12) -0.0135(10) -0.0047(10) -0.0078(11) C44 0.0529(18) 0.0369(15) 0.0297(14) -0.0194(12) -0.0035(12) -0.0145(13) C45 0.0465(17) 0.0327(14) 0.0345(15) -0.0206(12) 0.0051(12) -0.0106(12) C46 0.0343(14) 0.0338(14) 0.0425(16) -0.0169(12) -0.0007(12) -0.0038(11) C47 0.0338(13) 0.0345(14) 0.0295(13) -0.0118(11) -0.0057(10) -0.0086(11) N1S 0.108(4) 0.084(3) 0.055(3) -0.018(2) -0.025(3) -0.016(3) C1S 0.076(3) 0.074(3) 0.056(3) -0.027(2) -0.009(2) 0.000(3) C2S 0.114(6) 0.085(5) 0.087(5) 0.001(4) -0.002(4) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N17 2.013(2) 2_676 ? Cu1 N12 2.064(2) 2_676 ? Cu1 N1 2.136(2) . ? Cu1 Br2 2.3870(5) . ? Cu1 Br1 2.5548(5) . ? N1 C2 1.336(3) . ? N1 C6 1.368(3) . ? C2 N3 1.322(3) . ? C2 O7 1.336(3) . ? N3 C4 1.349(3) . ? C4 N5 1.333(3) . ? C4 N35 1.363(3) . ? N5 C6 1.346(3) . ? C6 N23 1.331(3) . ? O7 C8 1.450(3) . ? C8 C9 1.518(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.503(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.392(4) . ? C10 C11 1.393(3) . ? C11 N12 1.338(3) . ? C11 H11A 0.9500 . ? N12 C13 1.351(3) . ? N12 Cu1 2.064(2) 2_676 ? C13 C14 1.392(3) . ? C13 C16 1.478(3) . ? C14 C15 1.392(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 N17 1.348(3) . ? C16 C21 1.393(3) . ? N17 C18 1.342(3) . ? N17 Cu1 2.013(2) 2_676 ? C18 C19 1.391(4) . ? C18 H18A 0.9500 . ? C19 C20 1.393(4) . ? C19 C22 1.504(4) . ? C20 C21 1.384(4) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N23 C24 1.464(3) . ? N23 H23A 0.8800 . ? C24 C30 1.515(4) . ? C24 C25 1.522(4) . ? C24 H24 1.0000 . ? C25 C26 1.527(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 N27 1.489(4) . ? C26 C32 1.526(4) . ? C26 C31 1.541(5) . ? N27 O28 1.287(3) . ? N27 C29 1.489(4) . ? C29 C33 1.520(6) . ? C29 C34 1.534(6) . ? C29 C30 1.539(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? N35 C36 1.441(3) . ? N35 C42 1.441(3) . ? C36 C41 1.387(4) . ? C36 C37 1.388(4) . ? C37 C38 1.397(4) . ? C37 H37A 0.9500 . ? C38 C39 1.388(4) . ? C38 H38A 0.9500 . ? C39 C40 1.389(4) . ? C39 H39A 0.9500 . ? C40 C41 1.389(4) . ? C40 H40A 0.9500 . ? C41 H41A 0.9500 . ? C42 C47 1.387(4) . ? C42 C43 1.394(4) . ? C43 C44 1.394(4) . ? C43 H43A 0.9500 . ? C44 C45 1.385(5) . ? C44 H44A 0.9500 . ? C45 C46 1.392(5) . ? C45 H45A 0.9500 . ? C46 C47 1.393(4) . ? C46 H46A 0.9500 . ? C47 H47A 0.9500 . ? N1S C1S 1.137(7) . ? C1S C2S 1.468(9) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 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 N17 Cu1 N12 79.67(8) 2_676 2_676 ? N17 Cu1 N1 88.94(8) 2_676 . ? N12 Cu1 N1 125.56(8) 2_676 . ? N17 Cu1 Br2 173.70(6) 2_676 . ? N12 Cu1 Br2 95.13(6) 2_676 . ? N1 Cu1 Br2 91.24(6) . . ? N17 Cu1 Br1 90.97(6) 2_676 . ? N12 Cu1 Br1 125.47(6) 2_676 . ? N1 Cu1 Br1 107.60(5) . . ? Br2 Cu1 Br1 94.98(2) . . ? C2 N1 C6 113.4(2) . . ? C2 N1 Cu1 117.20(16) . . ? C6 N1 Cu1 129.12(16) . . ? N3 C2 O7 119.8(2) . . ? N3 C2 N1 127.5(2) . . ? O7 C2 N1 112.7(2) . . ? C2 N3 C4 113.3(2) . . ? N5 C4 N3 126.6(2) . . ? N5 C4 N35 116.9(2) . . ? N3 C4 N35 116.5(2) . . ? C4 N5 C6 114.3(2) . . ? N23 C6 N5 118.2(2) . . ? N23 C6 N1 117.0(2) . . ? N5 C6 N1 124.8(2) . . ? C2 O7 C8 118.18(19) . . ? O7 C8 C9 112.3(2) . . ? 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 . . ? C10 C9 C8 113.8(2) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C15 C10 C11 117.3(2) . . ? C15 C10 C9 122.2(2) . . ? C11 C10 C9 120.5(2) . . ? N12 C11 C10 123.5(2) . . ? N12 C11 H11A 118.3 . . ? C10 C11 H11A 118.3 . . ? C11 N12 C13 118.7(2) . . ? C11 N12 Cu1 127.19(17) . 2_676 ? C13 N12 Cu1 114.07(16) . 2_676 ? N12 C13 C14 121.8(2) . . ? N12 C13 C16 115.0(2) . . ? C14 C13 C16 123.2(2) . . ? C13 C14 C15 118.6(2) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C14 C15 C10 120.0(2) . . ? C14 C15 H15A 120.0 . . ? C10 C15 H15A 120.0 . . ? N17 C16 C21 121.4(2) . . ? N17 C16 C13 114.7(2) . . ? C21 C16 C13 123.9(2) . . ? C18 N17 C16 119.3(2) . . ? C18 N17 Cu1 124.21(18) . 2_676 ? C16 N17 Cu1 116.06(16) . 2_676 ? N17 C18 C19 122.9(2) . . ? N17 C18 H18A 118.5 . . ? C19 C18 H18A 118.5 . . ? C18 C19 C20 117.2(2) . . ? C18 C19 C22 121.2(3) . . ? C20 C19 C22 121.6(3) . . ? C21 C20 C19 120.4(2) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C16 118.7(2) . . ? C20 C21 H21A 120.7 . . ? C16 C21 H21A 120.7 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C6 N23 C24 122.7(2) . . ? C6 N23 H23A 118.6 . . ? C24 N23 H23A 118.6 . . ? N23 C24 C30 113.0(2) . . ? N23 C24 C25 108.3(2) . . ? C30 C24 C25 108.5(2) . . ? N23 C24 H24 109.0 . . ? C30 C24 H24 109.0 . . ? C25 C24 H24 109.0 . . ? C24 C25 C26 113.1(2) . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? N27 C26 C32 106.9(2) . . ? N27 C26 C25 110.2(2) . . ? C32 C26 C25 109.5(3) . . ? N27 C26 C31 109.0(3) . . ? C32 C26 C31 109.9(3) . . ? C25 C26 C31 111.2(3) . . ? O28 N27 C29 115.9(2) . . ? O28 N27 C26 115.4(3) . . ? C29 N27 C26 124.1(2) . . ? N27 C29 C33 107.7(3) . . ? N27 C29 C34 109.3(4) . . ? C33 C29 C34 109.3(4) . . ? N27 C29 C30 109.7(2) . . ? C33 C29 C30 108.8(4) . . ? C34 C29 C30 111.9(3) . . ? C24 C30 C29 112.0(3) . . ? C24 C30 H30A 109.2 . . ? C29 C30 H30A 109.2 . . ? C24 C30 H30B 109.2 . . ? C29 C30 H30B 109.2 . . ? H30A C30 H30B 107.9 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C26 C32 H32A 109.5 . . ? C26 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C26 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C33 H33A 109.5 . . ? C29 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C29 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C4 N35 C36 121.0(2) . . ? C4 N35 C42 121.1(2) . . ? C36 N35 C42 116.95(19) . . ? C41 C36 C37 120.2(2) . . ? C41 C36 N35 120.5(2) . . ? C37 C36 N35 119.2(2) . . ? C36 C37 C38 119.8(3) . . ? C36 C37 H37A 120.1 . . ? C38 C37 H37A 120.1 . . ? C39 C38 C37 120.0(3) . . ? C39 C38 H38A 120.0 . . ? C37 C38 H38A 120.0 . . ? C38 C39 C40 119.7(3) . . ? C38 C39 H39A 120.2 . . ? C40 C39 H39A 120.2 . . ? C39 C40 C41 120.5(3) . . ? C39 C40 H40A 119.7 . . ? C41 C40 H40A 119.7 . . ? C36 C41 C40 119.7(3) . . ? C36 C41 H41A 120.1 . . ? C40 C41 H41A 120.1 . . ? C47 C42 C43 120.9(2) . . ? C47 C42 N35 118.8(2) . . ? C43 C42 N35 120.2(2) . . ? C44 C43 C42 119.1(3) . . ? C44 C43 H43A 120.4 . . ? C42 C43 H43A 120.4 . . ? C45 C44 C43 120.3(3) . . ? C45 C44 H44A 119.9 . . ? C43 C44 H44A 119.9 . . ? C44 C45 C46 120.2(3) . . ? C44 C45 H45A 119.9 . . ? C46 C45 H45A 119.9 . . ? C45 C46 C47 120.0(3) . . ? C45 C46 H46A 120.0 . . ? C47 C46 H46A 120.0 . . ? C42 C47 C46 119.5(3) . . ? C42 C47 H47A 120.3 . . ? C46 C47 H47A 120.3 . . ? N1S C1S C2S 177.7(7) . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.627 _refine_diff_density_min -2.225 _refine_diff_density_rms 0.127 # Attachment 'Compound_8.CIF' data_zl56 _database_code_depnum_ccdc_archive 'CCDC 702600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H39 Br2 Cu N8 O2' _chemical_formula_weight 839.11 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 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' H H 0.0000 0.0000 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' N N -0.0031 0.0040 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' O O -0.0042 0.0074 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Cu Cu 0.1330 1.4803 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' Br Br -0.8064 2.7887 'WCROMER Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990' _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 9.7023(11) _cell_length_b 10.1421(11) _cell_length_c 20.239(2) _cell_angle_alpha 98.255(2) _cell_angle_beta 95.249(2) _cell_angle_gamma 113.578(2) _cell_volume 1781.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6019 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 33.17 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 3.594 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.58 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details 'TWINABS v. 2007/3 Bruker AXS Madison WI USA' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II 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 37239 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 33.64 _reflns_number_total 10609 _reflns_number_gt 8690 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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. No single crystals of this sample could be found, so data was collected on a non-merohedral twin. The two orientation matrices were determined using CELL_NOW (Sheldrick). TWINABS produced a merged Shelx HKLF4 file for the structure solution and HKLF5 for the refinement. The reported R(int) is that from merging in TWINABS 4.68% for all data 37239 observations. All non-hydrogens were refined anisotropically. Hydrogens were placed geometrically on all carbons, constrained and refined using a riding model. The Hydrogen on the nitrogen was found in the difference map and refined freely. ; _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^)+(0.0416P)^2^+0.4725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10609 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.59895(4) 0.84892(3) 0.161076(15) 0.02793(7) Uani 1 1 d . . . Cu1 Cu 0.54211(4) 0.71925(4) 0.047229(17) 0.02212(7) Uani 1 1 d . . . O1 O 0.0913(2) 0.3901(2) 0.12322(9) 0.0225(4) Uani 1 1 d . . . N1 N -0.0735(3) 0.4601(3) 0.17666(11) 0.0215(5) Uani 1 1 d . . . C1 C -0.1562(3) 0.4397(3) 0.22831(13) 0.0207(5) Uani 1 1 d . . . Br2 Br 0.70310(4) 0.60003(4) 0.062923(16) 0.03024(7) Uani 1 1 d . . . N2 N 0.0109(3) 0.2840(2) 0.20984(11) 0.0197(4) Uani 1 1 d . . . O2 O -0.5086(3) 0.7035(3) 0.43509(12) 0.0399(6) Uani 1 1 d . . . C2 C 0.0042(3) 0.3794(3) 0.17225(13) 0.0197(5) Uani 1 1 d . . . N3 N -0.1592(3) 0.3504(3) 0.27149(11) 0.0213(4) Uani 1 1 d . . . C3 C -0.0746(3) 0.2754(3) 0.25957(13) 0.0191(5) Uani 1 1 d . . . N4 N -0.0737(3) 0.1839(3) 0.30294(11) 0.0211(4) Uani 1 1 d . . . N5 N 0.3541(3) 0.7518(2) 0.02182(11) 0.0200(4) Uani 1 1 d . . . N6 N 0.5793(3) 0.7648(3) -0.04445(12) 0.0228(4) Uani 1 1 d . . . C4 C 0.0033(3) 0.0888(3) 0.29645(14) 0.0214(5) Uani 1 1 d . . . N7 N -0.2414(3) 0.5160(3) 0.23459(12) 0.0252(5) Uani 1 1 d . . . H7N H -0.238(4) 0.566(4) 0.2082(19) 0.034(10) Uiso 1 1 d . . . C5 C 0.0898(4) 0.0836(3) 0.35376(16) 0.0298(6) Uani 1 1 d . . . H5A H 0.1010 0.1457 0.3957 0.036 Uiso 1 1 calc R . . N8 N -0.4440(3) 0.6656(3) 0.38818(12) 0.0260(5) Uani 1 1 d . . . C6 C 0.1602(4) -0.0123(4) 0.35003(18) 0.0385(8) Uani 1 1 d . . . H6A H 0.2192 -0.0154 0.3894 0.046 Uiso 1 1 calc R . . C7 C 0.1447(4) -0.1027(4) 0.28955(18) 0.0394(8) Uani 1 1 d . . . H7A H 0.1941 -0.1669 0.2868 0.047 Uiso 1 1 calc R . . C10 C -0.1604(3) 0.1767(3) 0.35794(14) 0.0234(6) Uani 1 1 d . . . C8 C 0.0563(4) -0.0990(4) 0.23269(17) 0.0337(7) Uani 1 1 d . . . H8A H 0.0433 -0.1628 0.1911 0.040 Uiso 1 1 calc R . . C9 C -0.0135(3) -0.0030(3) 0.23573(15) 0.0270(6) Uani 1 1 d . . . H9A H -0.0726 -0.0003 0.1963 0.032 Uiso 1 1 calc R . . C11 C -0.0995(4) 0.2793(4) 0.41732(16) 0.0350(7) Uani 1 1 d . . . H11A H -0.0005 0.3563 0.4222 0.042 Uiso 1 1 calc R . . C12 C -0.1830(5) 0.2700(5) 0.47007(18) 0.0479(10) Uani 1 1 d . . . H12A H -0.1410 0.3406 0.5111 0.058 Uiso 1 1 calc R . . C13 C -0.3276(5) 0.1580(4) 0.4628(2) 0.0477(10) Uani 1 1 d . . . H13A H -0.3848 0.1519 0.4988 0.057 Uiso 1 1 calc R . . C14 C -0.3890(5) 0.0543(4) 0.4027(2) 0.0467(9) Uani 1 1 d . . . H14A H -0.4882 -0.0224 0.3975 0.056 Uiso 1 1 calc R . . C15 C -0.3047(4) 0.0634(4) 0.35022(17) 0.0330(7) Uani 1 1 d . . . H15A H -0.3457 -0.0075 0.3093 0.040 Uiso 1 1 calc R . . C16 C 0.0954(3) 0.4921(3) 0.07973(13) 0.0222(5) Uani 1 1 d . . . H16A H -0.0052 0.4957 0.0726 0.027 Uiso 1 1 calc R . . H16B H 0.1170 0.4582 0.0351 0.027 Uiso 1 1 calc R . . C17 C 0.2174(3) 0.6446(3) 0.11088(14) 0.0245(5) Uani 1 1 d . . . H17A H 0.1852 0.6881 0.1502 0.029 Uiso 1 1 calc R . . H17B H 0.3140 0.6388 0.1268 0.029 Uiso 1 1 calc R . . C18 C 0.2408(3) 0.7388(3) 0.05802(14) 0.0219(5) Uani 1 1 d . . . C19 C 0.1388(3) 0.7996(3) 0.04279(15) 0.0260(6) Uani 1 1 d . . . H19A H 0.0623 0.7938 0.0698 0.031 Uiso 1 1 calc R . . C20 C 0.1499(3) 0.8689(3) -0.01213(15) 0.0246(5) Uani 1 1 d . . . H20A H 0.0818 0.9118 -0.0226 0.029 Uiso 1 1 calc R . . C21 C 0.2605(3) 0.8749(3) -0.05142(14) 0.0237(5) Uani 1 1 d . . . H21A H 0.2677 0.9194 -0.0899 0.028 Uiso 1 1 calc R . . C22 C 0.3616(3) 0.8144(3) -0.03359(13) 0.0204(5) Uani 1 1 d . . . C23 C 0.4810(3) 0.8116(3) -0.07329(13) 0.0209(5) Uani 1 1 d . . . C24 C 0.4908(4) 0.8506(3) -0.13635(15) 0.0276(6) Uani 1 1 d . . . H24A H 0.4187 0.8806 -0.1565 0.033 Uiso 1 1 calc R . . C25 C 0.6087(4) 0.8446(3) -0.16946(15) 0.0300(6) Uani 1 1 d . . . H25A H 0.6190 0.8724 -0.2122 0.036 Uiso 1 1 calc R . . C26 C 0.7102(4) 0.7980(3) -0.13966(15) 0.0300(6) Uani 1 1 d . . . H26A H 0.7914 0.7936 -0.1614 0.036 Uiso 1 1 calc R . . C27 C 0.6915(3) 0.7577(3) -0.07733(15) 0.0271(6) Uani 1 1 d . . . H27A H 0.7601 0.7238 -0.0571 0.032 Uiso 1 1 calc R . . C29 C -0.3205(3) 0.5269(3) 0.29144(14) 0.0223(5) Uani 1 1 d . . . H29A H -0.3555 0.4329 0.3085 0.027 Uiso 1 1 calc R . . C30 C -0.2152(3) 0.6533(3) 0.34822(15) 0.0256(6) Uani 1 1 d . . . H30A H -0.1801 0.7453 0.3304 0.031 Uiso 1 1 calc R . . H30B H -0.1243 0.6363 0.3625 0.031 Uiso 1 1 calc R . . C31 C -0.2889(3) 0.6734(4) 0.41019(14) 0.0272(6) Uani 1 1 d . . . C32 C -0.5489(3) 0.5674(3) 0.32491(14) 0.0244(5) Uani 1 1 d . . . C33 C -0.4568(3) 0.5565(3) 0.26873(13) 0.0220(5) Uani 1 1 d . . . H33A H -0.5243 0.4768 0.2307 0.026 Uiso 1 1 calc R . . H33B H -0.4208 0.6495 0.2518 0.026 Uiso 1 1 calc R . . C34 C -0.6550(4) 0.6371(4) 0.30373(17) 0.0328(7) Uani 1 1 d . . . H34A H -0.5948 0.7334 0.2936 0.049 Uiso 1 1 calc R . . H34B H -0.7104 0.6489 0.3407 0.049 Uiso 1 1 calc R . . H34C H -0.7279 0.5738 0.2634 0.049 Uiso 1 1 calc R . . C35 C -0.6440(4) 0.4162(4) 0.34039(18) 0.0344(7) Uani 1 1 d . . . H35A H -0.7015 0.4275 0.3765 0.052 Uiso 1 1 calc R . . H35B H -0.5762 0.3720 0.3550 0.052 Uiso 1 1 calc R . . H35C H -0.7151 0.3527 0.2996 0.052 Uiso 1 1 calc R . . C36 C -0.3048(4) 0.5541(4) 0.45207(16) 0.0375(8) Uani 1 1 d . . . H36A H -0.3533 0.5693 0.4911 0.056 Uiso 1 1 calc R . . H36B H -0.2035 0.5601 0.4679 0.056 Uiso 1 1 calc R . . H36C H -0.3675 0.4572 0.4238 0.056 Uiso 1 1 calc R . . C37 C -0.1935(4) 0.8240(4) 0.45449(17) 0.0403(8) Uani 1 1 d . . . H37A H -0.1841 0.9001 0.4281 0.060 Uiso 1 1 calc R . . H37B H -0.0919 0.8312 0.4706 0.060 Uiso 1 1 calc R . . H37C H -0.2431 0.8378 0.4933 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03053(15) 0.02690(15) 0.02426(13) 0.00791(12) 0.00285(11) 0.00931(12) Cu1 0.02172(16) 0.02707(17) 0.02436(16) 0.01039(14) 0.00751(13) 0.01455(14) O1 0.0251(10) 0.0267(10) 0.0239(9) 0.0123(8) 0.0120(8) 0.0150(8) N1 0.0227(11) 0.0249(11) 0.0231(11) 0.0094(9) 0.0083(9) 0.0139(9) C1 0.0202(12) 0.0253(13) 0.0201(12) 0.0073(10) 0.0054(10) 0.0115(11) Br2 0.02905(15) 0.03836(17) 0.03620(16) 0.01626(14) 0.01037(13) 0.02320(13) N2 0.0183(11) 0.0237(11) 0.0220(10) 0.0086(9) 0.0077(8) 0.0116(9) O2 0.0438(14) 0.0569(16) 0.0307(11) 0.0022(11) 0.0138(10) 0.0334(13) C2 0.0204(12) 0.0204(12) 0.0195(12) 0.0054(10) 0.0058(9) 0.0089(10) N3 0.0219(11) 0.0258(12) 0.0220(11) 0.0099(9) 0.0087(9) 0.0130(10) C3 0.0165(12) 0.0230(12) 0.0195(11) 0.0053(10) 0.0033(9) 0.0095(10) N4 0.0243(12) 0.0273(12) 0.0206(10) 0.0114(9) 0.0097(9) 0.0164(10) N5 0.0209(11) 0.0183(10) 0.0222(10) 0.0053(9) 0.0061(9) 0.0088(9) N6 0.0241(11) 0.0216(11) 0.0257(11) 0.0069(9) 0.0075(9) 0.0112(9) C4 0.0207(13) 0.0221(13) 0.0265(13) 0.0113(11) 0.0087(10) 0.0108(10) N7 0.0313(13) 0.0343(13) 0.0240(11) 0.0160(10) 0.0137(10) 0.0226(11) C5 0.0308(16) 0.0326(16) 0.0314(15) 0.0100(13) 0.0046(12) 0.0175(13) N8 0.0268(13) 0.0323(13) 0.0240(11) 0.0054(10) 0.0074(9) 0.0171(11) C6 0.0349(18) 0.048(2) 0.0435(18) 0.0181(16) 0.0039(14) 0.0266(16) C7 0.0445(19) 0.049(2) 0.0492(19) 0.0246(17) 0.0209(16) 0.0369(17) C10 0.0310(15) 0.0292(14) 0.0220(12) 0.0125(11) 0.0121(11) 0.0206(12) C8 0.0427(18) 0.0329(16) 0.0373(16) 0.0104(14) 0.0178(14) 0.0244(15) C9 0.0265(14) 0.0302(15) 0.0292(14) 0.0106(12) 0.0080(11) 0.0145(12) C11 0.0470(19) 0.0359(17) 0.0269(15) 0.0078(13) 0.0084(14) 0.0213(15) C12 0.086(3) 0.049(2) 0.0289(16) 0.0118(16) 0.0229(18) 0.045(2) C13 0.073(3) 0.053(2) 0.050(2) 0.0326(18) 0.044(2) 0.046(2) C14 0.050(2) 0.047(2) 0.058(2) 0.0222(18) 0.0342(19) 0.0268(18) C15 0.0352(17) 0.0332(16) 0.0343(16) 0.0080(13) 0.0167(13) 0.0155(14) C16 0.0264(14) 0.0258(13) 0.0188(12) 0.0094(10) 0.0090(10) 0.0124(11) C17 0.0253(14) 0.0280(14) 0.0228(12) 0.0079(11) 0.0078(11) 0.0119(12) C18 0.0212(12) 0.0206(12) 0.0230(12) 0.0042(10) 0.0049(10) 0.0075(10) C19 0.0248(14) 0.0273(14) 0.0310(14) 0.0060(12) 0.0102(11) 0.0149(11) C20 0.0224(13) 0.0218(13) 0.0341(15) 0.0087(11) 0.0063(11) 0.0125(11) C21 0.0238(13) 0.0215(13) 0.0290(14) 0.0091(11) 0.0054(11) 0.0113(11) C22 0.0212(12) 0.0189(12) 0.0214(12) 0.0045(10) 0.0062(10) 0.0079(10) C23 0.0211(13) 0.0178(12) 0.0238(12) 0.0046(10) 0.0073(10) 0.0074(10) C24 0.0313(15) 0.0303(15) 0.0271(14) 0.0084(12) 0.0079(12) 0.0174(13) C25 0.0388(17) 0.0303(15) 0.0258(14) 0.0085(12) 0.0130(12) 0.0167(13) C26 0.0328(16) 0.0296(15) 0.0339(15) 0.0088(12) 0.0174(13) 0.0161(13) C27 0.0266(14) 0.0275(14) 0.0325(15) 0.0076(12) 0.0091(12) 0.0155(12) C29 0.0252(14) 0.0278(14) 0.0228(12) 0.0119(11) 0.0101(10) 0.0166(12) C30 0.0181(13) 0.0318(15) 0.0296(14) 0.0077(12) 0.0048(11) 0.0123(12) C31 0.0270(14) 0.0371(16) 0.0226(13) 0.0064(12) 0.0057(11) 0.0183(13) C32 0.0185(12) 0.0291(14) 0.0297(14) 0.0093(12) 0.0072(11) 0.0122(11) C33 0.0224(13) 0.0257(13) 0.0230(12) 0.0069(11) 0.0058(10) 0.0141(11) C34 0.0258(15) 0.0436(18) 0.0374(16) 0.0078(14) 0.0068(13) 0.0227(14) C35 0.0270(16) 0.0369(17) 0.0423(18) 0.0154(14) 0.0135(13) 0.0124(13) C36 0.044(2) 0.054(2) 0.0276(15) 0.0178(15) 0.0087(14) 0.0291(17) C37 0.0385(19) 0.045(2) 0.0308(16) -0.0014(14) -0.0034(14) 0.0154(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cu1 2.3791(5) . ? Cu1 N6 2.005(2) . ? Cu1 N5 2.015(2) . ? Cu1 Br2 2.3521(5) . ? O1 C2 1.350(3) . ? O1 C16 1.443(3) . ? N1 C2 1.316(3) . ? N1 C1 1.365(3) . ? C1 N3 1.340(3) . ? C1 N7 1.342(3) . ? N2 C2 1.331(3) . ? N2 C3 1.352(3) . ? O2 N8 1.280(3) . ? N3 C3 1.339(3) . ? C3 N4 1.368(3) . ? N4 C4 1.437(3) . ? N4 C10 1.448(3) . ? N5 C18 1.350(3) . ? N5 C22 1.359(3) . ? N6 C27 1.347(4) . ? N6 C23 1.348(3) . ? C4 C9 1.384(4) . ? C4 C5 1.388(4) . ? N7 C29 1.455(3) . ? N7 H7N 0.79(4) . ? C5 C6 1.392(4) . ? C5 H5A 0.9500 . ? N8 C31 1.497(4) . ? N8 C32 1.501(4) . ? C6 C7 1.376(5) . ? C6 H6A 0.9500 . ? C7 C8 1.385(5) . ? C7 H7A 0.9500 . ? C10 C11 1.377(4) . ? C10 C15 1.388(4) . ? C8 C9 1.388(4) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C11 C12 1.390(5) . ? C11 H11A 0.9500 . ? C12 C13 1.385(6) . ? C12 H12A 0.9500 . ? C13 C14 1.392(6) . ? C13 H13A 0.9500 . ? C14 C15 1.389(4) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.520(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.508(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.393(4) . ? C19 C20 1.388(4) . ? C19 H19A 0.9500 . ? C20 C21 1.380(4) . ? C20 H20A 0.9500 . ? C21 C22 1.396(4) . ? C21 H21A 0.9500 . ? C22 C23 1.477(4) . ? C23 C24 1.390(4) . ? C24 C25 1.394(4) . ? C24 H24A 0.9500 . ? C25 C26 1.380(4) . ? C25 H25A 0.9500 . ? C26 C27 1.386(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C29 C33 1.516(4) . ? C29 C30 1.524(4) . ? C29 H29A 1.0000 . ? C30 C31 1.528(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C37 1.522(5) . ? C31 C36 1.541(4) . ? C32 C33 1.527(4) . ? C32 C34 1.527(4) . ? C32 C35 1.536(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 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 N6 Cu1 N5 81.93(9) . . ? N6 Cu1 Br2 99.59(7) . . ? N5 Cu1 Br2 160.89(7) . . ? N6 Cu1 Br1 138.00(7) . . ? N5 Cu1 Br1 95.65(6) . . ? Br2 Cu1 Br1 95.713(17) . . ? C2 O1 C16 117.5(2) . . ? C2 N1 C1 112.5(2) . . ? N3 C1 N7 118.9(2) . . ? N3 C1 N1 125.5(2) . . ? N7 C1 N1 115.6(2) . . ? C2 N2 C3 112.2(2) . . ? N1 C2 N2 129.4(2) . . ? N1 C2 O1 118.3(2) . . ? N2 C2 O1 112.3(2) . . ? C3 N3 C1 114.3(2) . . ? N3 C3 N2 126.1(2) . . ? N3 C3 N4 116.1(2) . . ? N2 C3 N4 117.7(2) . . ? C3 N4 C4 124.4(2) . . ? C3 N4 C10 118.7(2) . . ? C4 N4 C10 116.9(2) . . ? C18 N5 C22 119.6(2) . . ? C18 N5 Cu1 127.61(18) . . ? C22 N5 Cu1 111.97(17) . . ? C27 N6 C23 118.9(2) . . ? C27 N6 Cu1 127.28(19) . . ? C23 N6 Cu1 113.75(17) . . ? C9 C4 C5 119.5(3) . . ? C9 C4 N4 121.8(2) . . ? C5 C4 N4 118.6(3) . . ? C1 N7 C29 124.5(2) . . ? C1 N7 H7N 117(3) . . ? C29 N7 H7N 118(3) . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? O2 N8 C31 116.1(2) . . ? O2 N8 C32 115.7(2) . . ? C31 N8 C32 123.9(2) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 119.4(3) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C11 C10 C15 120.6(3) . . ? C11 C10 N4 120.5(3) . . ? C15 C10 N4 118.9(3) . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8A 119.6 . . ? C9 C8 H8A 119.6 . . ? C4 C9 C8 119.8(3) . . ? C4 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C10 C15 C14 119.7(3) . . ? C10 C15 H15A 120.2 . . ? C14 C15 H15A 120.2 . . ? O1 C16 C17 110.6(2) . . ? O1 C16 H16A 109.5 . . ? C17 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C18 C17 C16 108.6(2) . . ? C18 C17 H17A 110.0 . . ? C16 C17 H17A 110.0 . . ? C18 C17 H17B 110.0 . . ? C16 C17 H17B 110.0 . . ? H17A C17 H17B 108.3 . . ? N5 C18 C19 120.8(2) . . ? N5 C18 C17 118.5(2) . . ? C19 C18 C17 120.4(2) . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C21 C20 C19 119.5(2) . . ? C21 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? C20 C21 C22 118.9(2) . . ? C20 C21 H21A 120.6 . . ? C22 C21 H21A 120.6 . . ? N5 C22 C21 121.4(2) . . ? N5 C22 C23 115.6(2) . . ? C21 C22 C23 123.1(2) . . ? N6 C23 C24 121.9(2) . . ? N6 C23 C22 114.9(2) . . ? C24 C23 C22 123.3(2) . . ? C23 C24 C25 118.6(3) . . ? C23 C24 H24A 120.7 . . ? C25 C24 H24A 120.7 . . ? C26 C25 C24 119.5(3) . . ? C26 C25 H25A 120.2 . . ? C24 C25 H25A 120.2 . . ? C25 C26 C27 118.7(3) . . ? C25 C26 H26A 120.6 . . ? C27 C26 H26A 120.6 . . ? N6 C27 C26 122.3(3) . . ? N6 C27 H27A 118.8 . . ? C26 C27 H27A 118.8 . . ? N7 C29 C33 109.5(2) . . ? N7 C29 C30 110.4(2) . . ? C33 C29 C30 108.2(2) . . ? N7 C29 H29A 109.6 . . ? C33 C29 H29A 109.6 . . ? C30 C29 H29A 109.6 . . ? C29 C30 C31 114.1(2) . . ? C29 C30 H30A 108.7 . . ? C31 C30 H30A 108.7 . . ? C29 C30 H30B 108.7 . . ? C31 C30 H30B 108.7 . . ? H30A C30 H30B 107.6 . . ? N8 C31 C37 107.8(2) . . ? N8 C31 C30 109.7(2) . . ? C37 C31 C30 109.8(3) . . ? N8 C31 C36 108.7(3) . . ? C37 C31 C36 109.4(3) . . ? C30 C31 C36 111.4(2) . . ? N8 C32 C33 110.0(2) . . ? N8 C32 C34 107.2(2) . . ? C33 C32 C34 109.3(2) . . ? N8 C32 C35 109.2(2) . . ? C33 C32 C35 111.8(2) . . ? C34 C32 C35 109.2(2) . . ? C29 C33 C32 113.3(2) . . ? C29 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C29 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.821 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.090 # Attachment 'Compound_5a.cif' data_zl09 _database_code_depnum_ccdc_archive 'CCDC 702601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 Cl N6 O' _chemical_formula_weight 494.97 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.3349(7) _cell_length_b 9.6066(8) _cell_length_c 31.311(3) _cell_angle_alpha 90.000(2) _cell_angle_beta 90.000(2) _cell_angle_gamma 90.000(2) _cell_volume 2507.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10816 _cell_measurement_theta_min 1.30 _cell_measurement_theta_max 29.52 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.785994 _exptl_absorpt_correction_T_max 1.0000000 _exptl_absorpt_process_details 'BRUKER AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean '8.192 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31276 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 29.52 _reflns_number_total 6449 _reflns_number_gt 3797 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(8) _refine_ls_number_reflns 6449 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.12786(10) 0.32977(10) 0.35509(2) 0.0833(3) Uani 1 1 d . . . O1 O 0.0352(2) 0.4073(2) 0.21014(5) 0.0625(5) Uani 1 1 d . . . N1 N -0.0328(2) 0.3711(2) 0.27801(6) 0.0541(5) Uani 1 1 d . . . N2 N 0.1219(2) 0.2173(2) 0.32101(6) 0.0518(5) Uani 1 1 d . . . N3 N 0.1964(2) 0.2587(2) 0.24827(6) 0.0463(5) Uani 1 1 d . . . N4 N 0.3519(2) 0.1208(2) 0.29266(6) 0.0464(5) Uani 1 1 d . . . N5 N 0.1474(5) 0.1246(3) 0.02408(8) 0.0962(9) Uani 1 1 d . . . N6 N 0.5151(4) 0.0216(3) 0.07413(8) 0.0832(8) Uani 1 1 d . . . C1 C 0.0026(3) 0.3029(3) 0.31297(7) 0.0521(6) Uani 1 1 d . . . C2 C 0.0702(3) 0.3406(3) 0.24633(7) 0.0477(5) Uani 1 1 d . . . C3 C 0.2201(3) 0.2002(2) 0.28681(7) 0.0433(5) Uani 1 1 d . . . C4 C 0.3888(3) 0.0592(2) 0.33315(7) 0.0471(5) Uani 1 1 d . . . C5 C 0.4153(4) 0.1400(3) 0.36895(8) 0.0678(8) Uani 1 1 d . . . H5 H 0.4100 0.2365 0.3672 0.081(2) Uiso 1 1 calc R . . C6 C 0.4495(5) 0.0768(4) 0.40717(10) 0.0867(10) Uani 1 1 d . . . H6 H 0.4645 0.1311 0.4314 0.081(2) Uiso 1 1 calc R . . C7 C 0.4619(4) -0.0653(4) 0.41014(10) 0.0807(9) Uani 1 1 d . . . H7 H 0.4866 -0.1072 0.4361 0.081(2) Uiso 1 1 calc R . . C8 C 0.4375(4) -0.1446(3) 0.37443(10) 0.0740(8) Uani 1 1 d . . . H8 H 0.4453 -0.2410 0.3762 0.081(2) Uiso 1 1 calc R . . C9 C 0.4017(3) -0.0835(3) 0.33624(9) 0.0592(7) Uani 1 1 d . . . H9 H 0.3860 -0.1385 0.3122 0.081(2) Uiso 1 1 calc R . . C10 C 0.4612(3) 0.0940(2) 0.25786(7) 0.0447(5) Uani 1 1 d . . . C11 C 0.4072(3) 0.0251(3) 0.22168(8) 0.0528(6) Uani 1 1 d . . . H11 H 0.3012 -0.0045 0.2196 0.081(2) Uiso 1 1 calc R . . C12 C 0.5144(3) 0.0014(3) 0.18863(8) 0.0576(7) Uani 1 1 d . . . H12 H 0.4799 -0.0439 0.1640 0.081(2) Uiso 1 1 calc R . . C13 C 0.6704(4) 0.0438(3) 0.19185(9) 0.0585(7) Uani 1 1 d . . . H13 H 0.7410 0.0285 0.1693 0.081(2) Uiso 1 1 calc R . . C14 C 0.7228(3) 0.1083(3) 0.22790(9) 0.0607(7) Uani 1 1 d . . . H14 H 0.8297 0.1350 0.2301 0.081(2) Uiso 1 1 calc R . . C15 C 0.6183(3) 0.1344(3) 0.26133(8) 0.0520(6) Uani 1 1 d . . . H15 H 0.6544 0.1789 0.2859 0.081(2) Uiso 1 1 calc R . . C16 C 0.1168(4) 0.3675(3) 0.17119(8) 0.0654(7) Uani 1 1 d . . . H16A H 0.2287 0.3477 0.1771 0.116(6) Uiso 1 1 calc R . . H16B H 0.1118 0.4429 0.1506 0.116(6) Uiso 1 1 calc R . . C17 C 0.0368(4) 0.2415(4) 0.15359(10) 0.0816(9) Uani 1 1 d . . . H17A H -0.0785 0.2541 0.1555 0.116(6) Uiso 1 1 calc R . . H17B H 0.0649 0.1622 0.1713 0.116(6) Uiso 1 1 calc R . . C18 C 0.0801(4) 0.2087(3) 0.10769(9) 0.0689(8) Uani 1 1 d . . . C19 C -0.0249(5) 0.2370(4) 0.07463(10) 0.0916(10) Uani 1 1 d . . . H19 H -0.1197 0.2856 0.0795 0.081(2) Uiso 1 1 calc R . . C20 C 0.0148(6) 0.1912(5) 0.03394(10) 0.1129(15) Uani 1 1 d . . . H20 H -0.0578 0.2089 0.0120 0.081(2) Uiso 1 1 calc R . . C21 C 0.2212(4) 0.1413(3) 0.09783(9) 0.0690(8) Uani 1 1 d . . . H21 H 0.2958 0.1225 0.1191 0.081(2) Uiso 1 1 calc R . . C22 C 0.2517(4) 0.1014(3) 0.05588(8) 0.0678(8) Uani 1 1 d . . . C23 C 0.4021(4) 0.0279(3) 0.04442(9) 0.0688(8) Uani 1 1 d . . . C24 C 0.4208(5) -0.0305(3) 0.00434(10) 0.0856(10) Uani 1 1 d . . . H24 H 0.3368 -0.0271 -0.0152 0.081(2) Uiso 1 1 calc R . . C25 C 0.5625(6) -0.0933(4) -0.00681(11) 0.0992(12) Uani 1 1 d . . . C26 C 0.6822(6) -0.0983(4) 0.02362(13) 0.1069(13) Uani 1 1 d . . . H26 H 0.7807 -0.1393 0.0176 0.081(2) Uiso 1 1 calc R . . C27 C 0.6522(6) -0.0411(4) 0.06304(12) 0.1035(12) Uani 1 1 d . . . H27 H 0.7330 -0.0464 0.0835 0.081(2) Uiso 1 1 calc R . . C28 C 0.5849(7) -0.1572(6) -0.05100(14) 0.157(2) Uani 1 1 d . . . H28A H 0.6078 -0.2547 -0.0482 0.231(17) Uiso 1 1 calc R . . H28B H 0.6726 -0.1121 -0.0653 0.231(17) Uiso 1 1 calc R . . H28C H 0.4886 -0.1451 -0.0674 0.231(17) 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 0.0762(5) 0.1199(7) 0.0537(4) 0.0054(4) 0.0190(4) 0.0366(5) O1 0.0655(11) 0.0782(12) 0.0440(9) 0.0004(8) -0.0016(8) 0.0211(10) N1 0.0475(11) 0.0686(13) 0.0463(11) 0.0005(10) 0.0034(9) 0.0140(10) N2 0.0498(12) 0.0596(13) 0.0461(10) -0.0001(9) 0.0074(9) 0.0090(11) N3 0.0437(11) 0.0511(11) 0.0443(10) -0.0015(9) 0.0040(8) 0.0064(9) N4 0.0424(11) 0.0488(11) 0.0479(10) 0.0025(9) 0.0026(9) 0.0068(9) N5 0.127(3) 0.107(2) 0.0553(14) -0.0049(14) 0.0007(16) 0.032(2) N6 0.098(2) 0.0887(18) 0.0634(15) -0.0140(14) 0.0105(16) 0.0007(17) C1 0.0464(14) 0.0658(16) 0.0440(12) -0.0048(12) 0.0062(10) 0.0097(13) C2 0.0465(13) 0.0547(14) 0.0420(12) -0.0030(11) -0.0024(10) 0.0027(11) C3 0.0433(12) 0.0411(12) 0.0454(12) -0.0024(10) -0.0010(10) -0.0006(10) C4 0.0435(13) 0.0514(14) 0.0465(12) 0.0070(10) 0.0012(10) 0.0054(11) C5 0.087(2) 0.0605(17) 0.0557(14) 0.0007(13) -0.0077(14) 0.0093(15) C6 0.108(3) 0.099(3) 0.0538(17) -0.0051(16) -0.0198(18) 0.013(2) C7 0.089(2) 0.090(2) 0.0636(18) 0.0260(17) -0.0038(17) 0.0203(19) C8 0.0784(19) 0.0627(18) 0.0809(19) 0.0179(16) 0.0056(16) 0.0118(16) C9 0.0688(18) 0.0487(15) 0.0599(15) 0.0029(12) 0.0042(13) 0.0059(13) C10 0.0402(12) 0.0431(13) 0.0507(13) 0.0026(10) -0.0001(10) 0.0038(10) C11 0.0450(14) 0.0547(15) 0.0587(14) -0.0082(12) -0.0050(11) 0.0033(11) C12 0.0601(17) 0.0606(16) 0.0521(13) -0.0106(13) -0.0003(12) 0.0111(14) C13 0.0621(18) 0.0528(15) 0.0607(15) 0.0016(13) 0.0154(13) 0.0103(13) C14 0.0435(14) 0.0575(16) 0.0812(18) 0.0017(14) 0.0079(14) -0.0038(12) C15 0.0471(13) 0.0478(14) 0.0609(14) -0.0047(11) -0.0038(12) -0.0034(11) C16 0.0677(17) 0.084(2) 0.0444(13) 0.0038(13) 0.0081(13) 0.0062(16) C17 0.0716(19) 0.101(2) 0.0724(19) -0.0137(18) 0.0192(16) -0.0075(19) C18 0.0727(19) 0.078(2) 0.0565(15) -0.0063(14) 0.0093(14) -0.0138(16) C19 0.096(3) 0.105(3) 0.074(2) -0.0047(19) 0.009(2) 0.026(2) C20 0.144(4) 0.137(3) 0.0580(19) 0.007(2) -0.007(2) 0.048(3) C21 0.0720(18) 0.081(2) 0.0541(15) -0.0101(15) 0.0088(14) -0.0160(16) C22 0.097(2) 0.0598(17) 0.0467(14) -0.0001(13) 0.0080(15) -0.0071(16) C23 0.093(2) 0.0593(17) 0.0546(15) -0.0068(13) 0.0163(16) -0.0099(16) C24 0.112(3) 0.084(2) 0.0605(17) -0.0201(16) 0.0106(19) 0.001(2) C25 0.127(3) 0.101(3) 0.069(2) -0.0303(19) 0.023(2) 0.000(3) C26 0.113(3) 0.106(3) 0.102(3) -0.027(2) 0.029(3) 0.011(3) C27 0.101(3) 0.121(3) 0.088(2) -0.014(2) 0.000(2) 0.006(3) C28 0.179(5) 0.197(5) 0.096(3) -0.063(3) 0.038(3) 0.013(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 Cl1 C1 1.729(2) . ? O1 C2 1.334(3) . ? O1 C16 1.448(3) . ? N1 C1 1.309(3) . ? N1 C2 1.344(3) . ? N2 C1 1.315(3) . ? N2 C3 1.358(3) . ? N3 C2 1.315(3) . ? N3 C3 1.345(3) . ? N4 C3 1.350(3) . ? N4 C4 1.432(3) . ? N4 C10 1.443(3) . ? N5 C20 1.313(5) . ? N5 C22 1.341(4) . ? N6 C23 1.325(4) . ? N6 C27 1.338(5) . ? C4 C9 1.379(3) . ? C4 C5 1.382(4) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 C8 1.368(4) . ? C7 H7 0.9300 . ? C8 C9 1.365(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C15 1.370(3) . ? C10 C11 1.387(3) . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 C13 1.366(4) . ? C12 H12 0.9300 . ? C13 C14 1.360(4) . ? C13 H13 0.9300 . ? C14 C15 1.384(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.488(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.515(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C21 1.378(4) . ? C18 C19 1.383(5) . ? C19 C20 1.388(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.392(4) . ? C21 H21 0.9300 . ? C22 C23 1.482(4) . ? C23 C24 1.384(4) . ? C24 C25 1.371(5) . ? C24 H24 0.9300 . ? C25 C26 1.380(6) . ? C25 C28 1.525(5) . ? C26 C27 1.374(5) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 O1 C16 119.07(19) . . ? C1 N1 C2 111.4(2) . . ? C1 N2 C3 112.36(19) . . ? C2 N3 C3 114.12(19) . . ? C3 N4 C4 121.89(19) . . ? C3 N4 C10 120.78(18) . . ? C4 N4 C10 117.33(18) . . ? C20 N5 C22 116.9(3) . . ? C23 N6 C27 116.5(3) . . ? N1 C1 N2 130.0(2) . . ? N1 C1 Cl1 114.94(18) . . ? N2 C1 Cl1 115.02(18) . . ? N3 C2 O1 120.12(19) . . ? N3 C2 N1 127.4(2) . . ? O1 C2 N1 112.5(2) . . ? N3 C3 N4 118.49(19) . . ? N3 C3 N2 124.6(2) . . ? N4 C3 N2 116.9(2) . . ? C9 C4 C5 119.3(2) . . ? C9 C4 N4 119.4(2) . . ? C5 C4 N4 121.3(2) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 121.0(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 119.2(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C9 C8 C7 120.6(3) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C4 120.4(3) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? C15 C10 C11 120.7(2) . . ? C15 C10 N4 119.5(2) . . ? C11 C10 N4 119.8(2) . . ? C12 C11 C10 118.6(2) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.5(3) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C10 C15 C14 119.4(2) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? O1 C16 C17 108.4(2) . . ? O1 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? O1 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C16 C17 C18 114.4(3) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C21 C18 C19 117.7(3) . . ? C21 C18 C17 120.9(3) . . ? C19 C18 C17 121.2(3) . . ? C18 C19 C20 118.3(3) . . ? C18 C19 H19 120.9 . . ? C20 C19 H19 120.9 . . ? N5 C20 C19 124.8(4) . . ? N5 C20 H20 117.6 . . ? C19 C20 H20 117.6 . . ? C18 C21 C22 119.8(3) . . ? C18 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? N5 C22 C21 122.4(3) . . ? N5 C22 C23 116.6(3) . . ? C21 C22 C23 121.0(3) . . ? N6 C23 C24 122.5(3) . . ? N6 C23 C22 116.9(2) . . ? C24 C23 C22 120.6(3) . . ? C25 C24 C23 120.4(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 117.5(3) . . ? C24 C25 C28 120.9(4) . . ? C26 C25 C28 121.6(4) . . ? C27 C26 C25 118.3(4) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? N6 C27 C26 124.6(4) . . ? N6 C27 H27 117.7 . . ? C26 C27 H27 117.7 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 29.52 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.279 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.041 # Attachment 'Compound_5b.cif' data_zl08 _database_code_depnum_ccdc_archive 'CCDC 702602' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 Cl N6 O' _chemical_formula_weight 494.97 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8067(8) _cell_length_b 10.8773(9) _cell_length_c 12.7401(11) _cell_angle_alpha 75.296(2) _cell_angle_beta 78.660(2) _cell_angle_gamma 70.606(2) _cell_volume 1230.46(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7095 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 29.04 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.654762 _exptl_absorpt_correction_T_max 1.0000000 _exptl_absorpt_process_details 'BRUKER AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean '8.192 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15197 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 29.04 _reflns_number_total 6001 _reflns_number_gt 3730 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6001 _refine_ls_number_parameters 407 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 N1 N -0.07093(15) 0.34929(15) 0.74758(11) 0.0668(4) Uani 1 1 d . . . N2 N 0.04750(14) 0.26058(13) 0.90869(10) 0.0604(3) Uani 1 1 d . . . N3 N 0.11137(13) 0.43572(13) 0.77284(10) 0.0574(3) Uani 1 1 d . . . N4 N 0.21902(14) 0.35217(13) 0.93127(10) 0.0572(3) Uani 1 1 d . . . N5 N 0.45171(17) 0.76003(15) 0.36543(11) 0.0701(4) Uani 1 1 d . . . N6 N 0.67661(17) 0.87187(16) 0.48968(12) 0.0741(4) Uani 1 1 d . . . O1 O -0.01185(12) 0.51400(12) 0.62254(9) 0.0718(3) Uani 1 1 d . . . Cl1 Cl -0.14493(6) 0.15765(6) 0.88668(4) 0.0873(2) Uani 1 1 d . . . C1 C -0.04456(17) 0.26901(17) 0.84208(14) 0.0621(4) Uani 1 1 d . . . C2 C 0.01274(17) 0.43100(16) 0.71766(13) 0.0594(4) Uani 1 1 d . . . C3 C 0.12344(16) 0.34911(15) 0.86857(12) 0.0538(3) Uani 1 1 d . . . C4 C 0.24525(16) 0.26201(15) 1.03451(12) 0.0551(4) Uani 1 1 d . . . C5 C 0.30818(19) 0.12736(18) 1.04053(16) 0.0688(4) Uani 1 1 d . . . C6 C 0.3408(2) 0.0451(2) 1.14071(17) 0.0759(5) Uani 1 1 d . . . C7 C 0.31171(19) 0.0966(2) 1.23299(16) 0.0747(5) Uani 1 1 d . . . C8 C 0.2479(2) 0.2301(2) 1.22719(15) 0.0728(5) Uani 1 1 d . . . C9 C 0.21432(18) 0.3130(2) 1.12806(13) 0.0628(4) Uani 1 1 d . . . C10 C 0.29238(16) 0.45347(16) 0.90040(12) 0.0546(4) Uani 1 1 d . . . C11 C 0.2144(2) 0.58339(18) 0.90396(14) 0.0667(4) Uani 1 1 d . . . C12 C 0.2861(3) 0.6787(2) 0.88155(15) 0.0786(5) Uani 1 1 d . . . C13 C 0.4345(3) 0.6431(2) 0.85622(15) 0.0825(6) Uani 1 1 d . . . C14 C 0.5120(2) 0.5146(3) 0.85174(16) 0.0815(6) Uani 1 1 d . . . C15 C 0.44060(19) 0.4178(2) 0.87375(14) 0.0674(4) Uani 1 1 d . . . C16 C 0.07408(19) 0.60731(18) 0.58166(16) 0.0681(4) Uani 1 1 d . . . C17 C 0.2227(2) 0.53929(19) 0.52949(15) 0.0678(4) Uani 1 1 d . . . C18 C 0.31945(18) 0.62908(17) 0.50120(13) 0.0622(4) Uani 1 1 d . . . C19 C 0.3583(2) 0.68829(19) 0.39497(14) 0.0717(5) Uani 1 1 d . . . C20 C 0.47250(19) 0.72846(19) 0.55358(14) 0.0678(4) Uani 1 1 d . . . C21 C 0.51063(17) 0.77786(15) 0.44490(12) 0.0569(4) Uani 1 1 d . . . C22 C 0.3778(2) 0.6538(2) 0.58172(14) 0.0707(5) Uani 1 1 d . . . C23 C 0.62145(16) 0.85008(15) 0.41001(12) 0.0575(4) Uani 1 1 d . . . C24 C 0.66843(19) 0.89030(17) 0.30096(14) 0.0644(4) Uani 1 1 d . . . C25 C 0.7732(2) 0.95507(19) 0.27283(16) 0.0706(4) Uani 1 1 d . . . C26 C 0.83128(19) 0.97942(18) 0.35258(16) 0.0712(5) Uani 1 1 d . . . C27 C 0.7778(2) 0.9353(2) 0.45897(17) 0.0785(5) Uani 1 1 d . . . C28 C 0.9476(3) 1.0485(3) 0.3271(2) 0.0989(7) Uani 1 1 d . . . H28A H 1.0381 0.9855 0.3475 0.155(6) Uiso 1 1 calc R . . H28B H 0.9198 1.1185 0.3673 0.155(6) Uiso 1 1 calc R . . H28C H 0.9590 1.0856 0.2502 0.155(6) Uiso 1 1 calc R . . H5 H 0.3264(19) 0.0932(17) 0.9768(14) 0.068(5) Uiso 1 1 d . . . H6 H 0.385(2) -0.040(2) 1.1447(17) 0.088(6) Uiso 1 1 d . . . H7 H 0.337(2) 0.038(2) 1.3014(17) 0.086(6) Uiso 1 1 d . . . H8 H 0.229(2) 0.267(2) 1.2870(18) 0.096(7) Uiso 1 1 d . . . H9 H 0.170(2) 0.3993(19) 1.1240(14) 0.072(5) Uiso 1 1 d . . . H11 H 0.115(2) 0.6077(19) 0.9201(15) 0.081(6) Uiso 1 1 d . . . H12 H 0.224(2) 0.769(2) 0.8868(16) 0.090(6) Uiso 1 1 d . . . H13 H 0.485(2) 0.709(2) 0.8404(15) 0.086(6) Uiso 1 1 d . . . H14 H 0.617(3) 0.485(2) 0.8315(18) 0.106(7) Uiso 1 1 d . . . H15 H 0.495(2) 0.324(2) 0.8674(15) 0.081(6) Uiso 1 1 d . . . H16A H 0.0210(19) 0.6775(18) 0.5254(15) 0.071(5) Uiso 1 1 d . . . H16B H 0.0799(19) 0.6447(17) 0.6468(15) 0.074(5) Uiso 1 1 d . . . H17A H 0.2696(19) 0.4537(18) 0.5819(14) 0.068(5) Uiso 1 1 d . . . H17B H 0.218(2) 0.5080(18) 0.4629(16) 0.078(5) Uiso 1 1 d . . . H19 H 0.317(2) 0.6710(19) 0.3383(16) 0.086(6) Uiso 1 1 d . . . H20 H 0.513(2) 0.745(2) 0.6083(18) 0.102(7) Uiso 1 1 d . . . H22 H 0.3530(19) 0.6178(17) 0.6554(16) 0.072(5) Uiso 1 1 d . . . H24 H 0.633(2) 0.869(2) 0.2491(17) 0.093(6) Uiso 1 1 d . . . H25 H 0.809(2) 0.9758(17) 0.1984(15) 0.073(5) Uiso 1 1 d . . . H27 H 0.815(2) 0.953(2) 0.5162(17) 0.094(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0629(8) 0.0864(9) 0.0672(8) -0.0183(7) -0.0183(6) -0.0355(7) N2 0.0581(7) 0.0737(8) 0.0609(8) -0.0172(6) -0.0105(6) -0.0304(6) N3 0.0565(7) 0.0700(8) 0.0562(7) -0.0135(6) -0.0182(5) -0.0254(6) N4 0.0601(7) 0.0680(8) 0.0545(7) -0.0081(6) -0.0190(5) -0.0298(6) N5 0.0810(9) 0.0811(9) 0.0572(8) -0.0042(7) -0.0240(7) -0.0346(8) N6 0.0781(10) 0.0900(10) 0.0666(8) -0.0194(7) -0.0192(7) -0.0329(8) O1 0.0706(7) 0.0896(8) 0.0668(7) -0.0073(6) -0.0285(5) -0.0340(6) Cl1 0.0880(3) 0.1080(4) 0.0924(4) -0.0204(3) -0.0131(3) -0.0624(3) C1 0.0558(9) 0.0780(10) 0.0667(10) -0.0246(8) -0.0077(7) -0.0308(8) C2 0.0556(8) 0.0717(10) 0.0605(9) -0.0185(8) -0.0160(7) -0.0228(7) C3 0.0503(8) 0.0653(9) 0.0537(8) -0.0177(7) -0.0110(6) -0.0206(7) C4 0.0484(8) 0.0667(9) 0.0559(8) -0.0071(7) -0.0144(6) -0.0239(7) C5 0.0724(11) 0.0692(11) 0.0702(11) -0.0155(9) -0.0147(8) -0.0240(9) C6 0.0705(11) 0.0638(11) 0.0904(14) -0.0013(10) -0.0205(9) -0.0209(9) C7 0.0604(10) 0.0944(14) 0.0646(11) 0.0073(10) -0.0131(8) -0.0312(10) C8 0.0650(10) 0.0988(15) 0.0554(10) -0.0141(10) -0.0089(8) -0.0258(10) C9 0.0589(9) 0.0730(11) 0.0593(9) -0.0141(8) -0.0143(7) -0.0189(8) C10 0.0588(9) 0.0669(9) 0.0480(8) -0.0095(6) -0.0173(6) -0.0273(7) C11 0.0687(11) 0.0741(11) 0.0652(10) -0.0164(8) -0.0147(8) -0.0260(9) C12 0.1071(16) 0.0717(12) 0.0718(11) -0.0128(9) -0.0251(10) -0.0390(12) C13 0.1074(17) 0.0953(15) 0.0705(12) -0.0035(10) -0.0296(11) -0.0628(14) C14 0.0669(12) 0.1128(17) 0.0778(12) -0.0077(11) -0.0183(9) -0.0470(12) C15 0.0585(9) 0.0794(12) 0.0688(10) -0.0099(9) -0.0166(7) -0.0253(9) C16 0.0656(10) 0.0682(10) 0.0732(11) -0.0083(9) -0.0250(8) -0.0188(8) C17 0.0698(10) 0.0759(11) 0.0641(10) -0.0186(9) -0.0177(8) -0.0213(9) C18 0.0617(9) 0.0691(10) 0.0592(9) -0.0111(7) -0.0165(7) -0.0202(8) C19 0.0845(12) 0.0865(12) 0.0556(9) -0.0078(8) -0.0255(8) -0.0358(10) C20 0.0686(10) 0.0905(12) 0.0562(9) -0.0187(8) -0.0161(8) -0.0314(9) C21 0.0571(8) 0.0583(8) 0.0564(8) -0.0124(7) -0.0186(7) -0.0116(7) C22 0.0736(11) 0.0967(13) 0.0501(9) -0.0117(9) -0.0127(8) -0.0358(10) C23 0.0557(8) 0.0572(8) 0.0599(9) -0.0133(7) -0.0177(7) -0.0100(7) C24 0.0668(10) 0.0699(10) 0.0621(10) -0.0145(8) -0.0176(8) -0.0212(8) C25 0.0696(11) 0.0747(11) 0.0691(11) -0.0138(9) -0.0088(9) -0.0241(9) C26 0.0631(10) 0.0697(10) 0.0860(13) -0.0203(9) -0.0139(9) -0.0204(8) C27 0.0796(12) 0.0948(13) 0.0786(12) -0.0241(10) -0.0220(10) -0.0370(10) C28 0.0949(15) 0.1141(17) 0.1124(17) -0.0322(14) -0.0107(12) -0.0574(14) _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 C1 1.311(2) . ? N1 C2 1.3408(19) . ? N2 C1 1.3231(19) . ? N2 C3 1.3491(19) . ? N3 C2 1.3233(18) . ? N3 C3 1.337(2) . ? N4 C3 1.3588(18) . ? N4 C4 1.4382(19) . ? N4 C10 1.4428(18) . ? N5 C19 1.334(2) . ? N5 C21 1.3419(19) . ? N6 C27 1.334(2) . ? N6 C23 1.342(2) . ? O1 C2 1.3254(19) . ? O1 C16 1.462(2) . ? Cl1 C1 1.7267(16) . ? C4 C5 1.376(2) . ? C4 C9 1.379(2) . ? C5 C6 1.387(3) . ? C5 H5 0.939(18) . ? C6 C7 1.369(3) . ? C6 H6 0.87(2) . ? C7 C8 1.366(3) . ? C7 H7 0.96(2) . ? C8 C9 1.380(2) . ? C8 H8 0.91(2) . ? C9 H9 0.888(19) . ? C10 C15 1.370(2) . ? C10 C11 1.373(2) . ? C11 C12 1.380(2) . ? C11 H11 0.92(2) . ? C12 C13 1.370(3) . ? C12 H12 0.98(2) . ? C13 C14 1.361(3) . ? C13 H13 0.96(2) . ? C14 C15 1.392(3) . ? C14 H14 0.98(2) . ? C15 H15 1.00(2) . ? C16 C17 1.505(3) . ? C16 H16A 0.986(18) . ? C16 H16B 1.031(18) . ? C17 C18 1.512(2) . ? C17 H17A 1.023(18) . ? C17 H17B 1.006(19) . ? C18 C19 1.382(2) . ? C18 C22 1.387(2) . ? C19 H19 0.98(2) . ? C20 C22 1.369(2) . ? C20 C21 1.378(2) . ? C20 H20 0.95(2) . ? C21 C23 1.482(2) . ? C22 H22 0.938(18) . ? C23 C24 1.381(2) . ? C24 C25 1.374(2) . ? C24 H24 0.91(2) . ? C25 C26 1.375(3) . ? C25 H25 0.942(18) . ? C26 C27 1.378(3) . ? C26 C28 1.507(3) . ? C27 H27 0.96(2) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 111.83(12) . . ? C1 N2 C3 112.02(13) . . ? C2 N3 C3 113.98(13) . . ? C3 N4 C4 122.56(12) . . ? C3 N4 C10 120.95(12) . . ? C4 N4 C10 116.35(10) . . ? C19 N5 C21 117.62(14) . . ? C27 N6 C23 117.11(15) . . ? C2 O1 C16 117.93(12) . . ? N1 C1 N2 129.65(14) . . ? N1 C1 Cl1 115.34(11) . . ? N2 C1 Cl1 115.01(13) . . ? N3 C2 O1 119.79(14) . . ? N3 C2 N1 126.90(15) . . ? O1 C2 N1 113.31(12) . . ? N3 C3 N2 125.61(12) . . ? N3 C3 N4 116.99(13) . . ? N2 C3 N4 117.39(13) . . ? C5 C4 C9 119.66(15) . . ? C5 C4 N4 121.21(14) . . ? C9 C4 N4 119.02(15) . . ? C4 C5 C6 119.33(18) . . ? C4 C5 H5 119.1(11) . . ? C6 C5 H5 121.6(11) . . ? C7 C6 C5 120.69(19) . . ? C7 C6 H6 119.2(14) . . ? C5 C6 H6 120.0(14) . . ? C8 C7 C6 119.96(18) . . ? C8 C7 H7 120.5(12) . . ? C6 C7 H7 119.5(12) . . ? C7 C8 C9 119.91(19) . . ? C7 C8 H8 121.8(14) . . ? C9 C8 H8 118.3(14) . . ? C4 C9 C8 120.44(19) . . ? C4 C9 H9 119.0(11) . . ? C8 C9 H9 120.5(11) . . ? C15 C10 C11 120.55(15) . . ? C15 C10 N4 119.55(15) . . ? C11 C10 N4 119.79(14) . . ? C10 C11 C12 119.73(19) . . ? C10 C11 H11 120.5(12) . . ? C12 C11 H11 119.7(12) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 124.8(12) . . ? C11 C12 H12 115.3(12) . . ? C14 C13 C12 120.50(18) . . ? C14 C13 H13 119.3(12) . . ? C12 C13 H13 120.2(12) . . ? C13 C14 C15 120.04(19) . . ? C13 C14 H14 123.7(14) . . ? C15 C14 H14 116.3(14) . . ? C10 C15 C14 119.27(19) . . ? C10 C15 H15 119.5(11) . . ? C14 C15 H15 121.2(11) . . ? O1 C16 C17 110.60(14) . . ? O1 C16 H16A 106.0(10) . . ? C17 C16 H16A 108.9(10) . . ? O1 C16 H16B 107.5(10) . . ? C17 C16 H16B 112.0(10) . . ? H16A C16 H16B 111.7(14) . . ? C16 C17 C18 110.98(14) . . ? C16 C17 H17A 109.6(10) . . ? C18 C17 H17A 109.4(9) . . ? C16 C17 H17B 112.3(11) . . ? C18 C17 H17B 110.3(10) . . ? H17A C17 H17B 104.0(14) . . ? C19 C18 C22 116.04(16) . . ? C19 C18 C17 122.75(14) . . ? C22 C18 C17 121.19(15) . . ? N5 C19 C18 124.85(15) . . ? N5 C19 H19 119.0(11) . . ? C18 C19 H19 116.0(11) . . ? C22 C20 C21 119.66(15) . . ? C22 C20 H20 120.3(13) . . ? C21 C20 H20 120.0(13) . . ? N5 C21 C20 121.55(15) . . ? N5 C21 C23 116.81(13) . . ? C20 C21 C23 121.62(13) . . ? C20 C22 C18 120.13(16) . . ? C20 C22 H22 120.4(11) . . ? C18 C22 H22 119.5(11) . . ? N6 C23 C24 121.51(15) . . ? N6 C23 C21 116.73(14) . . ? C24 C23 C21 121.74(13) . . ? C25 C24 C23 119.52(16) . . ? C25 C24 H24 121.3(13) . . ? C23 C24 H24 119.1(13) . . ? C24 C25 C26 120.32(17) . . ? C24 C25 H25 118.4(11) . . ? C26 C25 H25 121.1(11) . . ? C25 C26 C27 115.93(17) . . ? C25 C26 C28 122.86(18) . . ? C27 C26 C28 121.21(17) . . ? N6 C27 C26 125.61(17) . . ? N6 C27 H27 117.1(12) . . ? C26 C27 H27 117.3(12) . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 29.04 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.261 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.059 # Attachment '4-bpyT.cif' data_zl10 _database_code_depnum_ccdc_archive 'CCDC 702603' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H41 N8 O2' _chemical_formula_weight 629.78 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 10.8803(15) _cell_length_b 11.5566(15) _cell_length_c 15.819(2) _cell_angle_alpha 97.708(2) _cell_angle_beta 108.723(2) _cell_angle_gamma 110.203(2) _cell_volume 1699.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5843 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 29.64 _exptl_crystal_description prismatic _exptl_crystal_colour pink _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.868190 _exptl_absorpt_correction_T_max 1.0000000 _exptl_absorpt_process_details 'BRUKER AXS SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean '8.192 pixels/mm' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21470 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.64 _reflns_number_total 8568 _reflns_number_gt 3573 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement ? _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8568 _refine_ls_number_parameters 534 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1569 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 N1 N 0.42978(16) 0.33947(14) 1.01111(10) 0.0477(4) Uani 1 1 d . . . N2 N 0.21029(15) 0.19134(14) 0.88718(10) 0.0451(4) Uani 1 1 d . . . N3 N 0.31553(16) 0.12671(14) 1.01815(11) 0.0508(4) Uani 1 1 d . . . N4 N 0.10859(16) -0.01512(14) 0.89390(10) 0.0502(4) Uani 1 1 d . . . N5 N 0.5815(2) -0.06960(18) 1.41416(13) 0.0700(5) Uani 1 1 d . . . N6 N 0.45174(18) -0.29396(18) 1.19293(13) 0.0621(5) Uani 1 1 d . . . N7 N 0.31135(17) 0.40261(15) 0.89037(10) 0.0492(4) Uani 1 1 d . . . N8 N 0.01928(18) 0.41179(16) 0.64128(11) 0.0587(5) Uani 1 1 d . . . O1 O 0.52650(14) 0.27280(12) 1.13110(9) 0.0640(4) Uani 1 1 d . . . O2 O -0.08047(17) 0.39813(17) 0.56469(10) 0.0868(5) Uani 1 1 d . . . C1 C 0.31702(19) 0.30851(17) 0.92989(12) 0.0419(5) Uani 1 1 d . . . C2 C 0.4174(2) 0.24316(18) 1.04921(13) 0.0472(5) Uani 1 1 d . . . C3 C 0.21559(19) 0.10537(17) 0.93414(13) 0.0447(5) Uani 1 1 d . . . C4 C -0.0074(2) -0.04012(17) 0.80753(13) 0.0478(5) Uani 1 1 d . . . C5 C -0.0106(3) -0.1015(2) 0.72627(17) 0.0716(7) Uani 1 1 d . . . C6 C -0.1227(4) -0.1240(3) 0.6435(2) 0.0940(10) Uani 1 1 d . . . C7 C -0.2282(3) -0.0873(3) 0.6424(2) 0.0828(9) Uani 1 1 d . . . C8 C -0.2253(3) -0.0270(3) 0.7228(2) 0.0767(8) Uani 1 1 d . . . C9 C -0.1145(2) -0.0029(2) 0.80598(17) 0.0625(6) Uani 1 1 d . . . C10 C 0.1070(2) -0.11918(17) 0.93488(12) 0.0465(5) Uani 1 1 d . . . C11 C -0.0138(3) -0.1931(2) 0.94495(15) 0.0571(6) Uani 1 1 d . . . C12 C -0.0143(3) -0.2920(2) 0.98592(17) 0.0686(7) Uani 1 1 d . . . C13 C 0.1047(3) -0.3155(2) 1.01711(16) 0.0714(7) Uani 1 1 d . . . C14 C 0.2248(3) -0.2433(2) 1.00524(16) 0.0685(7) Uani 1 1 d . . . C15 C 0.2255(3) -0.1461(2) 0.96389(15) 0.0576(6) Uani 1 1 d . . . C16 C 0.5101(3) 0.1792(3) 1.1839(2) 0.0864(10) Uani 1 1 d . . . C17 C 0.6491(3) 0.1960(3) 1.2485(2) 0.0787(8) Uani 1 1 d . . . C18 C 0.6287(2) 0.1036(2) 1.30782(16) 0.0632(6) Uani 1 1 d . . . C19 C 0.6568(3) 0.1458(3) 1.39990(17) 0.0742(7) Uani 1 1 d . . . C20 C 0.6334(3) 0.0572(3) 1.44935(19) 0.0820(8) Uani 1 1 d . . . C21 C 0.5518(2) -0.1115(2) 1.32386(14) 0.0518(5) Uani 1 1 d . . . C22 C 0.5753(2) -0.0273(2) 1.27036(17) 0.0625(6) Uani 1 1 d . . . C23 C 0.4928(2) -0.2522(2) 1.28521(15) 0.0532(5) Uani 1 1 d . . . C24 C 0.4784(2) -0.3360(2) 1.34037(18) 0.0588(6) Uani 1 1 d . . . C25 C 0.4208(2) -0.4664(2) 1.30174(19) 0.0651(6) Uani 1 1 d . . . C26 C 0.3771(2) -0.5085(3) 1.2061(2) 0.0733(7) Uani 1 1 d . . . C27 C 0.3956(3) -0.4203(3) 1.1565(2) 0.0704(7) Uani 1 1 d . . . C28 C 0.4048(3) -0.5596(2) 1.3594(2) 0.0969(9) Uani 1 1 d . . . H28A H 0.4933 -0.5673 1.3862 0.117(2) Uiso 1 1 calc R . . H28B H 0.3314 -0.6418 1.3209 0.117(2) Uiso 1 1 calc R . . H28C H 0.3796 -0.5290 1.4081 0.117(2) Uiso 1 1 calc R . . C29 C 0.1947(2) 0.38124(18) 0.80356(12) 0.0441(5) Uani 1 1 d . . . C30 C 0.2426(2) 0.3931(2) 0.72461(14) 0.0518(5) Uani 1 1 d . . . C31 C 0.1196(2) 0.35430(19) 0.63142(13) 0.0514(5) Uani 1 1 d . . . C32 C -0.0068(2) 0.44142(19) 0.72615(14) 0.0513(5) Uani 1 1 d . . . C33 C 0.1266(2) 0.4735(2) 0.81241(14) 0.0520(5) Uani 1 1 d . . . C34 C -0.0420(3) 0.5581(2) 0.72532(17) 0.0807(7) Uani 1 1 d . . . H34A H 0.0359 0.6283 0.7237 0.117(2) Uiso 1 1 calc R . . H34B H -0.0575 0.5819 0.7803 0.117(2) Uiso 1 1 calc R . . H34C H -0.1267 0.5377 0.6715 0.117(2) Uiso 1 1 calc R . . C35 C -0.1335(2) 0.3269(2) 0.72249(17) 0.0773(7) Uani 1 1 d . . . H35A H -0.2111 0.3011 0.6634 0.117(2) Uiso 1 1 calc R . . H35B H -0.1624 0.3504 0.7710 0.117(2) Uiso 1 1 calc R . . H35C H -0.1066 0.2570 0.7308 0.117(2) Uiso 1 1 calc R . . C36 C 0.0386(3) 0.2093(2) 0.59513(15) 0.0783(7) Uani 1 1 d . . . H36A H 0.0052 0.1765 0.6400 0.117(2) Uiso 1 1 calc R . . H36B H 0.1006 0.1722 0.5846 0.117(2) Uiso 1 1 calc R . . H36C H -0.0413 0.1877 0.5379 0.117(2) Uiso 1 1 calc R . . C37 C 0.1756(3) 0.4063(2) 0.56136(15) 0.0786(7) Uani 1 1 d . . . H37A H 0.0975 0.3808 0.5025 0.117(2) Uiso 1 1 calc R . . H37B H 0.2423 0.3728 0.5546 0.117(2) Uiso 1 1 calc R . . H37C H 0.2222 0.4983 0.5828 0.117(2) Uiso 1 1 calc R . . H5 H 0.070(2) -0.112(2) 0.7298(16) 0.082(9) Uiso 1 1 d . . . H6 H -0.120(3) -0.164(3) 0.594(2) 0.113(11) Uiso 1 1 d . . . H7 H -0.313(3) -0.108(3) 0.581(2) 0.146(12) Uiso 1 1 d . . . H7N H 0.389(2) 0.4818(19) 0.9201(13) 0.060(6) Uiso 1 1 d . . . H8 H -0.304(3) 0.001(2) 0.7239(17) 0.098(9) Uiso 1 1 d . . . H9 H -0.117(2) 0.032(2) 0.8633(16) 0.084(8) Uiso 1 1 d . . . H11 H -0.096(2) -0.1728(19) 0.9245(14) 0.074(7) Uiso 1 1 d . . . H12 H -0.095(3) -0.335(2) 0.9972(16) 0.091(8) Uiso 1 1 d . . . H13 H 0.101(2) -0.386(2) 1.0470(15) 0.081(7) Uiso 1 1 d . . . H14 H 0.311(3) -0.259(2) 1.0253(15) 0.090(8) Uiso 1 1 d . . . H15 H 0.308(2) -0.0984(17) 0.9546(12) 0.052(6) Uiso 1 1 d . . . H16A H 0.456(4) 0.189(3) 1.227(2) 0.166(16) Uiso 1 1 d . . . H16B H 0.463(4) 0.109(3) 1.147(2) 0.162(17) Uiso 1 1 d . . . H17A H 0.700(3) 0.295(3) 1.288(2) 0.137(11) Uiso 1 1 d . . . H17B H 0.698(4) 0.175(3) 1.202(2) 0.173(15) Uiso 1 1 d . . . H19 H 0.692(2) 0.240(2) 1.4287(16) 0.095(8) Uiso 1 1 d . . . H20 H 0.652(3) 0.083(2) 1.5146(18) 0.097(8) Uiso 1 1 d . . . H22 H 0.550(2) -0.066(2) 1.2080(15) 0.072(7) Uiso 1 1 d . . . H24 H 0.504(2) -0.3030(19) 1.4041(14) 0.063(7) Uiso 1 1 d . . . H26 H 0.329(2) -0.603(2) 1.1755(14) 0.075(7) Uiso 1 1 d . . . H27 H 0.366(3) -0.447(2) 1.0878(18) 0.102(9) Uiso 1 1 d . . . H29 H 0.1228(16) 0.2934(15) 0.7934(10) 0.035(4) Uiso 1 1 d . . . H30A H 0.320(2) 0.4795(19) 0.7381(13) 0.064(6) Uiso 1 1 d . . . H30B H 0.293(2) 0.338(2) 0.7222(13) 0.069(7) Uiso 1 1 d . . . H33A H 0.094(2) 0.4651(17) 0.8654(14) 0.061(6) Uiso 1 1 d . . . H33B H 0.200(2) 0.563(2) 0.8217(13) 0.070(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0457(10) 0.0377(9) 0.0409(9) 0.0128(7) 0.0025(8) 0.0089(7) N2 0.0423(9) 0.0344(9) 0.0418(9) 0.0104(7) 0.0049(7) 0.0080(7) N3 0.0453(10) 0.0391(9) 0.0462(10) 0.0140(7) 0.0014(8) 0.0076(8) N4 0.0464(10) 0.0336(9) 0.0461(10) 0.0111(7) -0.0007(8) 0.0062(7) N5 0.0823(14) 0.0612(13) 0.0493(12) 0.0198(10) 0.0116(10) 0.0219(10) N6 0.0585(12) 0.0668(13) 0.0577(12) 0.0154(10) 0.0137(9) 0.0313(10) N7 0.0451(10) 0.0359(9) 0.0423(10) 0.0118(8) -0.0019(8) 0.0066(8) N8 0.0581(11) 0.0723(12) 0.0462(11) 0.0192(9) 0.0088(9) 0.0372(10) O1 0.0537(9) 0.0499(8) 0.0529(9) 0.0229(7) -0.0073(7) 0.0044(7) O2 0.0784(11) 0.1222(15) 0.0537(10) 0.0245(9) 0.0013(9) 0.0575(11) C1 0.0402(11) 0.0392(11) 0.0376(11) 0.0114(9) 0.0093(9) 0.0119(9) C2 0.0434(12) 0.0417(12) 0.0417(11) 0.0130(9) 0.0051(9) 0.0111(9) C3 0.0420(11) 0.0358(11) 0.0447(12) 0.0105(9) 0.0096(9) 0.0102(9) C4 0.0477(13) 0.0341(10) 0.0443(13) 0.0093(9) 0.0068(10) 0.0084(9) C5 0.086(2) 0.0642(16) 0.0556(17) 0.0106(12) 0.0168(15) 0.0339(15) C6 0.133(3) 0.0723(19) 0.0430(17) 0.0008(14) 0.0120(19) 0.0314(19) C7 0.079(2) 0.0614(17) 0.0609(19) 0.0225(14) -0.0081(17) 0.0072(15) C8 0.0552(16) 0.0743(17) 0.078(2) 0.0286(15) 0.0061(15) 0.0172(14) C9 0.0547(15) 0.0660(15) 0.0531(15) 0.0159(12) 0.0100(13) 0.0202(12) C10 0.0503(13) 0.0337(10) 0.0405(11) 0.0077(9) 0.0067(10) 0.0118(9) C11 0.0579(15) 0.0459(13) 0.0566(14) 0.0131(11) 0.0178(12) 0.0140(11) C12 0.0804(19) 0.0500(14) 0.0641(16) 0.0165(12) 0.0313(14) 0.0114(14) C13 0.101(2) 0.0453(14) 0.0553(15) 0.0187(12) 0.0176(14) 0.0261(15) C14 0.0759(18) 0.0467(14) 0.0660(16) 0.0141(12) 0.0064(14) 0.0268(13) C15 0.0548(14) 0.0454(13) 0.0610(14) 0.0146(11) 0.0153(12) 0.0145(11) C16 0.0653(18) 0.077(2) 0.0782(19) 0.0505(17) -0.0072(17) 0.0083(16) C17 0.0733(18) 0.0698(18) 0.0775(18) 0.0399(15) 0.0095(15) 0.0235(15) C18 0.0555(14) 0.0593(15) 0.0615(15) 0.0260(12) 0.0056(11) 0.0217(11) C19 0.0826(18) 0.0554(16) 0.0579(16) 0.0167(13) 0.0043(13) 0.0196(13) C20 0.100(2) 0.0676(18) 0.0498(15) 0.0145(14) 0.0115(14) 0.0195(15) C21 0.0465(12) 0.0576(13) 0.0492(13) 0.0201(11) 0.0113(10) 0.0244(10) C22 0.0683(16) 0.0658(16) 0.0507(15) 0.0221(13) 0.0148(12) 0.0306(13) C23 0.0429(12) 0.0625(14) 0.0550(14) 0.0197(11) 0.0139(10) 0.0267(11) C24 0.0506(14) 0.0644(16) 0.0636(16) 0.0254(13) 0.0190(12) 0.0269(12) C25 0.0465(13) 0.0598(15) 0.0909(19) 0.0315(14) 0.0217(13) 0.0250(11) C26 0.0524(15) 0.0585(17) 0.092(2) 0.0104(16) 0.0132(14) 0.0221(13) C27 0.0609(15) 0.0685(18) 0.0692(18) 0.0103(15) 0.0116(13) 0.0288(13) C28 0.090(2) 0.0745(18) 0.133(2) 0.0506(18) 0.0426(18) 0.0341(15) C29 0.0401(11) 0.0374(11) 0.0408(11) 0.0113(9) 0.0038(9) 0.0113(9) C30 0.0485(13) 0.0556(14) 0.0502(13) 0.0149(11) 0.0147(11) 0.0245(12) C31 0.0536(13) 0.0559(13) 0.0396(12) 0.0095(10) 0.0099(10) 0.0261(11) C32 0.0466(12) 0.0575(13) 0.0508(13) 0.0147(10) 0.0164(10) 0.0254(10) C33 0.0497(13) 0.0565(14) 0.0454(13) 0.0111(10) 0.0148(11) 0.0217(11) C34 0.0787(17) 0.0803(17) 0.0925(19) 0.0225(14) 0.0247(14) 0.0525(15) C35 0.0501(14) 0.0867(18) 0.0848(18) 0.0266(14) 0.0215(13) 0.0205(13) C36 0.0868(18) 0.0663(16) 0.0603(15) -0.0005(12) 0.0091(13) 0.0326(14) C37 0.0884(19) 0.0993(19) 0.0562(14) 0.0295(14) 0.0306(13) 0.0432(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.322(2) . ? N1 C1 1.359(2) . ? N2 C3 1.324(2) . ? N2 C1 1.343(2) . ? N3 C2 1.313(2) . ? N3 C3 1.345(2) . ? N4 C3 1.366(2) . ? N4 C10 1.438(2) . ? N4 C4 1.442(2) . ? N5 C21 1.338(3) . ? N5 C20 1.335(3) . ? N6 C27 1.330(3) . ? N6 C23 1.344(2) . ? N7 C1 1.335(2) . ? N7 C29 1.460(2) . ? N7 H7N 0.93(2) . ? N8 O2 1.2873(19) . ? N8 C32 1.479(3) . ? N8 C31 1.497(3) . ? O1 C2 1.348(2) . ? O1 C16 1.450(3) . ? C4 C9 1.370(3) . ? C4 C5 1.366(3) . ? C5 C6 1.391(4) . ? C5 H5 0.91(2) . ? C6 C7 1.350(4) . ? C6 H6 0.87(3) . ? C7 C8 1.351(4) . ? C7 H7 1.03(3) . ? C8 C9 1.383(3) . ? C8 H8 1.02(2) . ? C9 H9 0.96(2) . ? C10 C11 1.371(3) . ? C10 C15 1.380(3) . ? C11 C12 1.387(3) . ? C11 H11 0.97(2) . ? C12 C13 1.365(3) . ? C12 H12 0.94(2) . ? C13 C14 1.373(4) . ? C13 H13 0.99(2) . ? C14 C15 1.373(3) . ? C14 H14 0.98(2) . ? C15 H15 0.949(18) . ? C16 C17 1.456(4) . ? C16 H16A 1.05(4) . ? C16 H16B 0.81(4) . ? C17 C18 1.520(3) . ? C17 H17A 1.07(3) . ? C17 H17B 1.08(4) . ? C18 C19 1.369(3) . ? C18 C22 1.381(3) . ? C19 C20 1.374(3) . ? C19 H19 1.00(2) . ? C20 H20 0.97(2) . ? C21 C22 1.385(3) . ? C21 C23 1.480(3) . ? C22 H22 0.93(2) . ? C23 C24 1.390(3) . ? C24 C25 1.375(3) . ? C24 H24 0.94(2) . ? C25 C26 1.390(3) . ? C25 C28 1.503(3) . ? C26 C27 1.368(3) . ? C26 H26 1.00(2) . ? C27 H27 1.00(2) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.505(3) . ? C29 C33 1.509(3) . ? C29 H29 0.998(16) . ? C30 C31 1.519(3) . ? C30 H30A 1.00(2) . ? C30 H30B 0.97(2) . ? C31 C36 1.520(3) . ? C31 C37 1.523(3) . ? C32 C35 1.524(3) . ? C32 C34 1.525(3) . ? C32 C33 1.526(3) . ? C33 H33A 1.02(2) . ? C33 H33B 1.02(2) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? 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 C1 112.25(16) . . ? C3 N2 C1 114.57(15) . . ? C2 N3 C3 113.00(16) . . ? C3 N4 C10 122.21(15) . . ? C3 N4 C4 119.50(15) . . ? C10 N4 C4 118.29(15) . . ? C21 N5 C20 116.5(2) . . ? C27 N6 C23 116.6(2) . . ? C1 N7 C29 122.17(16) . . ? C1 N7 H7N 115.8(12) . . ? C29 N7 H7N 122.0(12) . . ? O2 N8 C32 115.47(17) . . ? O2 N8 C31 115.24(16) . . ? C32 N8 C31 125.90(15) . . ? C2 O1 C16 116.41(17) . . ? N7 C1 N2 117.68(16) . . ? N7 C1 N1 117.20(16) . . ? N2 C1 N1 125.11(16) . . ? N3 C2 N1 128.93(17) . . ? N3 C2 O1 117.81(16) . . ? N1 C2 O1 113.26(16) . . ? N2 C3 N3 125.82(17) . . ? N2 C3 N4 116.79(16) . . ? N3 C3 N4 117.39(16) . . ? C9 C4 C5 119.6(2) . . ? C9 C4 N4 120.7(2) . . ? C5 C4 N4 119.7(2) . . ? C4 C5 C6 118.9(3) . . ? C4 C5 H5 115.9(15) . . ? C6 C5 H5 124.2(15) . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 124(2) . . ? C5 C6 H6 115(2) . . ? C8 C7 C6 119.8(3) . . ? C8 C7 H7 119.2(17) . . ? C6 C7 H7 120.9(17) . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 121.4(14) . . ? C9 C8 H8 118.5(15) . . ? C4 C9 C8 120.4(3) . . ? C4 C9 H9 119.4(14) . . ? C8 C9 H9 119.9(14) . . ? C11 C10 C15 119.5(2) . . ? C11 C10 N4 119.68(19) . . ? C15 C10 N4 120.85(19) . . ? C10 C11 C12 119.6(2) . . ? C10 C11 H11 118.5(13) . . ? C12 C11 H11 121.9(13) . . ? C13 C12 C11 120.6(3) . . ? C13 C12 H12 121.5(15) . . ? C11 C12 H12 117.5(15) . . ? C12 C13 C14 119.8(2) . . ? C12 C13 H13 118.2(13) . . ? C14 C13 H13 122.0(13) . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 118.0(14) . . ? C13 C14 H14 122.1(14) . . ? C14 C15 C10 120.6(2) . . ? C14 C15 H15 119.0(11) . . ? C10 C15 H15 120.4(11) . . ? O1 C16 C17 110.2(2) . . ? O1 C16 H16A 114(2) . . ? C17 C16 H16A 103.8(19) . . ? O1 C16 H16B 107(3) . . ? C17 C16 H16B 115(3) . . ? H16A C16 H16B 107(3) . . ? C16 C17 C18 109.2(2) . . ? C16 C17 H17A 105.1(16) . . ? C18 C17 H17A 113.4(15) . . ? C16 C17 H17B 102.4(19) . . ? C18 C17 H17B 113.4(19) . . ? H17A C17 H17B 112(3) . . ? C19 C18 C22 116.9(2) . . ? C19 C18 C17 121.5(2) . . ? C22 C18 C17 121.5(2) . . ? C18 C19 C20 118.7(3) . . ? C18 C19 H19 119.0(13) . . ? C20 C19 H19 122.3(13) . . ? N5 C20 C19 125.1(3) . . ? N5 C20 H20 113.7(15) . . ? C19 C20 H20 121.3(15) . . ? N5 C21 C22 121.5(2) . . ? N5 C21 C23 116.09(18) . . ? C22 C21 C23 122.4(2) . . ? C18 C22 C21 121.3(2) . . ? C18 C22 H22 123.7(13) . . ? C21 C22 H22 114.9(13) . . ? N6 C23 C24 122.1(2) . . ? N6 C23 C21 115.58(18) . . ? C24 C23 C21 122.3(2) . . ? C25 C24 C23 120.6(2) . . ? C25 C24 H24 120.0(13) . . ? C23 C24 H24 119.3(13) . . ? C24 C25 C26 116.8(2) . . ? C24 C25 C28 122.0(3) . . ? C26 C25 C28 121.2(2) . . ? C27 C26 C25 119.3(3) . . ? C27 C26 H26 121.9(12) . . ? C25 C26 H26 118.7(12) . . ? N6 C27 C26 124.6(3) . . ? N6 C27 H27 114.1(14) . . ? C26 C27 H27 121.3(15) . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N7 C29 C30 112.16(17) . . ? N7 C29 C33 111.86(16) . . ? C30 C29 C33 108.38(17) . . ? N7 C29 H29 103.9(9) . . ? C30 C29 H29 112.7(9) . . ? C33 C29 H29 107.8(9) . . ? C29 C30 C31 112.85(18) . . ? C29 C30 H30A 111.8(11) . . ? C31 C30 H30A 113.2(11) . . ? C29 C30 H30B 108.1(12) . . ? C31 C30 H30B 109.1(12) . . ? H30A C30 H30B 101.0(16) . . ? N8 C31 C36 108.99(17) . . ? N8 C31 C30 109.60(17) . . ? C36 C31 C30 111.25(18) . . ? N8 C31 C37 107.47(17) . . ? C36 C31 C37 109.61(18) . . ? C30 C31 C37 109.84(18) . . ? N8 C32 C35 108.70(17) . . ? N8 C32 C34 106.81(17) . . ? C35 C32 C34 109.96(19) . . ? N8 C32 C33 110.26(17) . . ? C35 C32 C33 111.57(18) . . ? C34 C32 C33 109.42(18) . . ? C29 C33 C32 112.23(17) . . ? C29 C33 H33A 108.5(11) . . ? C32 C33 H33A 105.9(11) . . ? C29 C33 H33B 107.4(12) . . ? C32 C33 H33B 109.0(11) . . ? H33A C33 H33B 114.0(16) . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 29.64 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.150 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.035 # Attachment 'Ligand_6-bpyT.CIF' data_zl19 _database_code_depnum_ccdc_archive 'CCDC 702604' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H39.25 N8 O2.13' _chemical_formula_weight 618.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0020 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' _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 12.0789(13) _cell_length_b 17.5848(18) _cell_length_c 17.6973(18) _cell_angle_alpha 63.904(2) _cell_angle_beta 78.702(2) _cell_angle_gamma 89.122(2) _cell_volume 3299.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9911 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 33.40 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1313 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details 'SADABS 2007/4' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.77490 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Advanced Light Source station 11.3.1' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II 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 47124 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_sigmaI/netI 0.0862 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 33.60 _reflns_number_total 19590 _reflns_number_gt 14893 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker SAINT v7.34a' _computing_data_reduction 'Bruker SAINT v7.34a' _computing_structure_solution SIR97 _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL & local programs' _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 atoms were refined aniostropically except those in the minor part of the disorder and the partial water molecule. Displacement parameter restrains were used in modelling the disorder. Two carbons have displacement parameter ratios max:min around 5.5:1 in the disordered molecule, as this reflected the increase displacement of the phenyl rings in which they are a part it was decide to leave them unrestrained. The hydrogens on the water could not be found and so were omitted from the refinement. The N-H hydrogen were found in the difference map and were allow to refine freely. The methyl hydrogens were found in the difference map and the rest were placed geometrical, and refined using a riding 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^)+(0.1318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 19590 _refine_ls_number_parameters 910 _refine_ls_number_restraints 351 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.2029 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.62721(9) -0.02669(7) 0.05191(7) 0.0244(2) Uani 1 1 d . . . C1 C 0.58151(10) 0.04175(8) 0.05374(8) 0.0238(2) Uani 1 1 d . . . N2 N 0.60194(9) 0.12168(7) -0.00597(7) 0.0259(2) Uani 1 1 d . . . C2 C 0.70449(10) -0.00828(8) -0.02180(8) 0.0234(2) Uani 1 1 d . . . N3 N 0.73332(9) 0.06954(7) -0.08839(7) 0.0250(2) Uani 1 1 d . . . C3 C 0.67930(11) 0.13133(8) -0.07615(8) 0.0251(2) Uani 1 1 d . . . N4 N 0.70438(10) 0.21421(7) -0.13882(7) 0.0284(2) Uani 1 1 d . . . C4 C 0.63886(12) 0.28010(8) -0.12958(9) 0.0307(3) Uani 1 1 d . . . C5 C 0.69365(15) 0.34708(10) -0.12693(12) 0.0440(4) Uani 1 1 d . . . H5 H 0.7727 0.3479 -0.1283 0.053 Uiso 1 1 calc R . . C6 C 0.63286(18) 0.41314(11) -0.12224(13) 0.0520(4) Uani 1 1 d . . . H6 H 0.6709 0.4593 -0.1209 0.062 Uiso 1 1 calc R . . C7 C 0.51788(17) 0.41245(11) -0.11946(11) 0.0479(4) Uani 1 1 d . . . H7 H 0.4765 0.4577 -0.1162 0.057 Uiso 1 1 calc R . . C8 C 0.46397(16) 0.34503(11) -0.12150(12) 0.0463(4) Uani 1 1 d . . . H8 H 0.3847 0.3440 -0.1193 0.056 Uiso 1 1 calc R . . C9 C 0.52331(14) 0.27864(10) -0.12678(10) 0.0373(3) Uani 1 1 d . . . H9 H 0.4852 0.2327 -0.1285 0.045 Uiso 1 1 calc R . . C10 C 0.79404(12) 0.24067(8) -0.21329(9) 0.0290(3) Uani 1 1 d . . . C11 C 0.77408(13) 0.30360(9) -0.29091(9) 0.0353(3) Uani 1 1 d . . . H11 H 0.7021 0.3260 -0.2930 0.042 Uiso 1 1 calc R . . C12 C 0.85899(16) 0.33349(11) -0.36500(11) 0.0460(4) Uani 1 1 d . . . H12 H 0.8446 0.3762 -0.4175 0.055 Uiso 1 1 calc R . . C13 C 0.96312(17) 0.30186(11) -0.36289(12) 0.0529(5) Uani 1 1 d . . . H13 H 1.0205 0.3218 -0.4139 0.063 Uiso 1 1 calc R . . C14 C 0.98454(15) 0.24036(11) -0.28556(13) 0.0506(4) Uani 1 1 d . . . H14 H 1.0571 0.2188 -0.2839 0.061 Uiso 1 1 calc R . . C15 C 0.90045(13) 0.21007(9) -0.21032(11) 0.0384(3) Uani 1 1 d . . . H15 H 0.9160 0.1688 -0.1575 0.046 Uiso 1 1 calc R . . O1 O 0.50759(8) 0.02489(6) 0.12734(6) 0.0290(2) Uani 1 1 d . . . C16 C 0.45133(11) 0.09498(9) 0.13565(9) 0.0296(3) Uani 1 1 d . . . H16A H 0.3828 0.0722 0.1824 0.036 Uiso 1 1 calc R . . H16B H 0.4266 0.1309 0.0815 0.036 Uiso 1 1 calc R . . C17 C 0.52685(12) 0.14984(10) 0.15511(10) 0.0332(3) Uani 1 1 d . . . H17A H 0.5643 0.1131 0.2022 0.040 Uiso 1 1 calc R . . H17B H 0.5865 0.1830 0.1035 0.040 Uiso 1 1 calc R . . C18 C 0.45687(12) 0.20931(9) 0.18118(9) 0.0300(3) Uani 1 1 d . . . C19 C 0.46550(13) 0.29605(10) 0.12737(10) 0.0362(3) Uani 1 1 d . . . H19 H 0.5159 0.3196 0.0727 0.043 Uiso 1 1 calc R . . C20 C 0.39889(14) 0.34734(10) 0.15535(10) 0.0395(3) Uani 1 1 d . . . H20 H 0.4035 0.4069 0.1200 0.047 Uiso 1 1 calc R . . C21 C 0.32578(13) 0.31142(9) 0.23485(10) 0.0349(3) Uani 1 1 d . . . H21 H 0.2800 0.3458 0.2551 0.042 Uiso 1 1 calc R . . C22 C 0.32038(11) 0.22364(9) 0.28491(9) 0.0287(3) Uani 1 1 d . . . N5 N 0.38476(10) 0.17323(7) 0.25814(7) 0.0292(2) Uani 1 1 d . . . C23 C 0.24102(12) 0.18058(9) 0.36977(9) 0.0318(3) Uani 1 1 d . . . C24 C 0.23877(13) 0.09315(10) 0.42009(10) 0.0357(3) Uani 1 1 d . . . H24 H 0.2897 0.0602 0.4014 0.043 Uiso 1 1 calc R . . C25 C 0.16126(16) 0.05522(12) 0.49754(11) 0.0479(4) Uani 1 1 d . . . H25 H 0.1574 -0.0043 0.5327 0.058 Uiso 1 1 calc R . . C26 C 0.08966(18) 0.10569(14) 0.52268(12) 0.0603(5) Uani 1 1 d . . . H26 H 0.0349 0.0815 0.5752 0.072 Uiso 1 1 calc R . . C27 C 0.09925(18) 0.19229(14) 0.46966(12) 0.0623(6) Uani 1 1 d . . . H27 H 0.0509 0.2268 0.4879 0.075 Uiso 1 1 calc R . . N6 N 0.17265(13) 0.22982(10) 0.39438(9) 0.0483(4) Uani 1 1 d . . . N7 N 0.75532(9) -0.07527(7) -0.02670(7) 0.0263(2) Uani 1 1 d . . . C29 C 0.84990(10) -0.06693(8) -0.09581(8) 0.0237(2) Uani 1 1 d . . . H29 H 0.8450 -0.0141 -0.1488 0.028 Uiso 1 1 calc R . . C30 C 0.84683(10) -0.14320(8) -0.11503(8) 0.0248(2) Uani 1 1 d . . . H30A H 0.7722 -0.1497 -0.1276 0.030 Uiso 1 1 calc R . . H30B H 0.8550 -0.1951 -0.0632 0.030 Uiso 1 1 calc R . . C31 C 0.93966(11) -0.13522(8) -0.19080(8) 0.0271(2) Uani 1 1 d . . . N8 N 1.05103(9) -0.10934(8) -0.18113(8) 0.0307(2) Uani 1 1 d . . . O2 O 1.13813(10) -0.11188(8) -0.23459(8) 0.0490(3) Uani 1 1 d . . . C32 C 1.06586(12) -0.05135(10) -0.14240(11) 0.0383(3) Uani 1 1 d . . . C33 C 0.96277(12) -0.06180(11) -0.07174(10) 0.0367(3) Uani 1 1 d . . . H33A H 0.9672 -0.1141 -0.0192 0.044 Uiso 1 1 calc R . . H33B H 0.9657 -0.0132 -0.0579 0.044 Uiso 1 1 calc R . . C34 C 1.17056(15) -0.07586(16) -0.10345(16) 0.0639(6) Uani 1 1 d . . . H34A H 1.1601 -0.1358 -0.0611 0.096 Uiso 1 1 calc R . . H34B H 1.1819 -0.0405 -0.0751 0.096 Uiso 1 1 calc R . . H34C H 1.2370 -0.0670 -0.1491 0.096 Uiso 1 1 calc R . . C35 C 1.08430(15) 0.04063(11) -0.21500(14) 0.0553(5) Uani 1 1 d . . . H35A H 1.1370 0.0424 -0.2656 0.083 Uiso 1 1 calc R . . H35B H 1.1159 0.0779 -0.1952 0.083 Uiso 1 1 calc R . . H35C H 1.0117 0.0599 -0.2303 0.083 Uiso 1 1 calc R . . C36 C 0.91351(16) -0.07018(11) -0.27608(10) 0.0422(4) Uani 1 1 d . . . H36A H 0.9110 -0.0141 -0.2768 0.063 Uiso 1 1 calc R . . H36B H 0.8401 -0.0871 -0.2821 0.063 Uiso 1 1 calc R . . H36C H 0.9727 -0.0677 -0.3239 0.063 Uiso 1 1 calc R . . C37 C 0.94909(14) -0.22159(10) -0.19234(10) 0.0371(3) Uani 1 1 d . . . H37A H 1.0063 -0.2158 -0.2426 0.056 Uiso 1 1 calc R . . H37B H 0.8757 -0.2415 -0.1957 0.056 Uiso 1 1 calc R . . H37C H 0.9713 -0.2627 -0.1397 0.056 Uiso 1 1 calc R . . N1' N 0.25190(18) 0.21940(12) -0.15845(12) 0.0251(4) Uani 0.746(2) 1 d PU A 1 C1' C 0.17882(18) 0.27804(12) -0.16389(11) 0.0260(4) Uani 0.746(2) 1 d PU A 1 N2' N 0.16863(16) 0.34888(11) -0.23192(10) 0.0255(3) Uani 0.746(2) 1 d PU A 1 C3' C 0.2407(3) 0.3581(2) -0.30460(19) 0.0240(5) Uani 0.746(2) 1 d PU A 1 N3' N 0.3142(3) 0.3024(2) -0.3110(2) 0.0231(5) Uani 0.746(2) 1 d PU A 1 C2' C 0.3183(4) 0.2357(4) -0.2354(4) 0.0242(7) Uani 0.746(2) 1 d PU A 1 N1" N 0.2794(5) 0.2317(4) -0.1544(4) 0.0211(12) Uiso 0.254(2) 1 d PU A 2 C1" C 0.2175(5) 0.2946(4) -0.1589(4) 0.0242(11) Uiso 0.254(2) 1 d PU A 2 N2" N 0.2030(5) 0.3643(3) -0.2277(3) 0.0235(11) Uiso 0.254(2) 1 d PU A 2 C3" C 0.2627(8) 0.3642(7) -0.3005(7) 0.0240(18) Uiso 0.254(2) 1 d PU A 2 N3" N 0.3332(8) 0.3103(7) -0.3097(8) 0.0201(16) Uiso 0.254(2) 1 d PU A 2 C2" C 0.3359(12) 0.2392(11) -0.2343(12) 0.0206(19) Uiso 0.254(2) 1 d PU A 2 N4' N 0.23791(11) 0.43143(7) -0.37647(7) 0.0312(3) Uani 1 1 d . . . C4' C 0.16911(12) 0.49652(8) -0.36845(8) 0.0318(3) Uani 1 1 d . A . C5' C 0.06849(15) 0.50925(11) -0.39651(11) 0.0427(4) Uani 1 1 d . . . H5' H 0.0449 0.4763 -0.4219 0.051 Uiso 1 1 calc R A . C6' C 0.00168(17) 0.57149(13) -0.38703(12) 0.0541(5) Uani 1 1 d . A . H6' H -0.0685 0.5801 -0.4051 0.065 Uiso 1 1 calc R . . C7' C 0.03675(18) 0.62040(11) -0.35173(11) 0.0522(5) Uani 1 1 d . . . H7' H -0.0090 0.6626 -0.3457 0.063 Uiso 1 1 calc R A . C8' C 0.13809(17) 0.60806(10) -0.32525(11) 0.0488(4) Uani 1 1 d . A . H8' H 0.1625 0.6419 -0.3011 0.059 Uiso 1 1 calc R . . C9' C 0.20475(15) 0.54619(10) -0.33380(10) 0.0402(3) Uani 1 1 d . . . H9' H 0.2749 0.5380 -0.3158 0.048 Uiso 1 1 calc R A . C10' C 0.29624(12) 0.44648(9) -0.46107(8) 0.0312(3) Uani 1 1 d . A . C11' C 0.36218(14) 0.52304(10) -0.51252(10) 0.0416(4) Uani 1 1 d . . . H11' H 0.3714 0.5622 -0.4901 0.050 Uiso 1 1 calc R A . C12' C 0.41435(16) 0.54178(12) -0.59663(11) 0.0554(5) Uani 1 1 d . A . H12' H 0.4594 0.5938 -0.6319 0.067 Uiso 1 1 calc R . . C13' C 0.4009(2) 0.48519(14) -0.62891(11) 0.0650(7) Uani 1 1 d . . . H13' H 0.4358 0.4986 -0.6868 0.078 Uiso 1 1 calc R A . C14' C 0.3364(2) 0.40821(14) -0.57738(12) 0.0597(6) Uani 1 1 d . A . H14' H 0.3280 0.3691 -0.6000 0.072 Uiso 1 1 calc R . . C15' C 0.28420(15) 0.38842(11) -0.49272(10) 0.0422(4) Uani 1 1 d . . . H15' H 0.2408 0.3357 -0.4571 0.051 Uiso 1 1 calc R A . O1' O 0.10727(13) 0.25920(9) -0.08852(8) 0.0343(4) Uani 0.746(2) 1 d PU A 1 C16' C 0.01854(17) 0.31521(13) -0.08680(12) 0.0334(4) Uani 0.746(2) 1 d PU A 1 H16C H -0.0451 0.2833 -0.0379 0.040 Uiso 0.746(2) 1 calc PR A 1 H16D H -0.0102 0.3356 -0.1406 0.040 Uiso 0.746(2) 1 calc PR A 1 C17' C 0.06154(18) 0.39045(14) -0.07782(13) 0.0369(4) Uani 0.746(2) 1 d PU A 1 H17C H 0.1077 0.3710 -0.0332 0.044 Uiso 0.746(2) 1 calc PR A 1 H17D H 0.1102 0.4307 -0.1330 0.044 Uiso 0.746(2) 1 calc PR A 1 C18' C -0.03701(17) 0.43462(12) -0.05305(12) 0.0326(4) Uani 0.746(2) 1 d PU A 1 C19' C -0.0575(2) 0.51627(14) -0.10820(14) 0.0400(5) Uani 0.746(2) 1 d PU A 1 H19' H -0.0099 0.5466 -0.1635 0.048 Uiso 0.746(2) 1 calc PR A 1 C20' C -0.1505(3) 0.5526(2) -0.0799(2) 0.0390(7) Uani 0.746(2) 1 d PU A 1 H20' H -0.1659 0.6089 -0.1154 0.047 Uiso 0.746(2) 1 calc PR A 1 C21' C -0.2205(4) 0.5055(3) 0.0009(3) 0.0312(7) Uani 0.746(2) 1 d PU A 1 H21' H -0.2856 0.5281 0.0206 0.037 Uiso 0.746(2) 1 calc PR A 1 C22' C -0.1925(3) 0.4258(3) 0.0508(2) 0.0295(6) Uani 0.746(2) 1 d PU A 1 N5' N -0.10389(15) 0.38956(11) 0.02449(10) 0.0297(4) Uani 0.746(2) 1 d PU A 1 O1" O 0.1660(3) 0.2879(2) -0.0810(2) 0.0271(8) Uiso 0.254(2) 1 d PU A 2 C16" C 0.1009(5) 0.3554(4) -0.0769(4) 0.0310(11) Uiso 0.254(2) 1 d PU A 2 H16E H 0.1451 0.4102 -0.1162 0.037 Uiso 0.254(2) 1 calc PR A 2 H16F H 0.0892 0.3500 -0.0177 0.037 Uiso 0.254(2) 1 calc PR A 2 C17" C -0.0131(5) 0.3570(4) -0.1002(4) 0.0363(12) Uiso 0.254(2) 1 d PU A 2 H17E H -0.0032 0.3803 -0.1634 0.044 Uiso 0.254(2) 1 calc PR A 2 H17F H -0.0495 0.2985 -0.0735 0.044 Uiso 0.254(2) 1 calc PR A 2 C18" C -0.0865(5) 0.4108(4) -0.0690(4) 0.0306(10) Uiso 0.254(2) 1 d PU A 2 C19" C -0.0903(6) 0.4959(5) -0.1225(5) 0.0399(13) Uiso 0.254(2) 1 d PU A 2 H19" H -0.0471 0.5200 -0.1799 0.048 Uiso 0.254(2) 1 calc PR A 2 C20" C -0.1545(12) 0.5446(9) -0.0942(8) 0.0374(19) Uiso 0.254(2) 1 d PU A 2 H20" H -0.1618 0.6018 -0.1328 0.045 Uiso 0.254(2) 1 calc PR A 2 C21" C -0.2079(14) 0.5135(11) -0.0125(10) 0.035(2) Uiso 0.254(2) 1 d PU A 2 H21" H -0.2451 0.5493 0.0101 0.042 Uiso 0.254(2) 1 calc PR A 2 C22" C -0.2080(11) 0.4198(9) 0.0434(9) 0.0285(19) Uiso 0.254(2) 1 d PU A 2 N5" N -0.1458(4) 0.3722(3) 0.0131(3) 0.0282(10) Uiso 0.254(2) 1 d PU A 2 C23' C -0.26394(12) 0.37398(10) 0.13739(10) 0.0336(3) Uani 1 1 d . . . C24' C -0.25190(14) 0.28740(10) 0.18325(10) 0.0404(3) Uani 1 1 d . A . H24' H -0.2006 0.2593 0.1581 0.048 Uiso 1 1 calc R . . C25' C -0.31570(17) 0.24315(13) 0.26572(12) 0.0545(5) Uani 1 1 d . . . H25' H -0.3091 0.1842 0.2984 0.065 Uiso 1 1 calc R A . C26' C -0.38897(18) 0.28636(16) 0.29941(13) 0.0622(6) Uani 1 1 d . A . H26' H -0.4337 0.2578 0.3561 0.075 Uiso 1 1 calc R . . C27' C -0.39672(16) 0.37166(15) 0.24995(13) 0.0569(5) Uani 1 1 d . . . H27' H -0.4483 0.4005 0.2740 0.068 Uiso 1 1 calc R A . N6' N -0.33581(12) 0.41646(10) 0.16987(9) 0.0423(3) Uani 1 1 d . A . N7' N 0.39679(10) 0.17905(7) -0.23479(7) 0.0273(2) Uani 1 1 d . . . C29' C 0.45525(10) 0.17487(8) -0.31300(8) 0.0241(2) Uani 1 1 d . A . H29' H 0.4488 0.2292 -0.3640 0.029 Uiso 1 1 calc R . . C30' C 0.57983(11) 0.16095(8) -0.31291(8) 0.0274(2) Uani 1 1 d . . . H30C H 0.5862 0.1064 -0.2632 0.033 Uiso 1 1 calc R A . H30D H 0.6155 0.2070 -0.3057 0.033 Uiso 1 1 calc R . . C31' C 0.64408(11) 0.15933(8) -0.39588(9) 0.0297(3) Uani 1 1 d . A . N8' N 0.57793(10) 0.10480(7) -0.41944(8) 0.0314(2) Uani 1 1 d . . . O2' O 0.63092(11) 0.08784(8) -0.48005(8) 0.0483(3) Uani 1 1 d . A . C32' C 0.45189(12) 0.09507(9) -0.40309(8) 0.0290(3) Uani 1 1 d . A . C33' C 0.40128(11) 0.10159(9) -0.32024(8) 0.0277(3) Uani 1 1 d . . . H33C H 0.3192 0.1083 -0.3170 0.033 Uiso 1 1 calc R A . H33D H 0.4099 0.0478 -0.2705 0.033 Uiso 1 1 calc R . . C34' C 0.41697(15) 0.00688(10) -0.39245(10) 0.0408(3) Uani 1 1 d . . . H34D H 0.4359 0.0060 -0.4485 0.061 Uiso 1 1 calc R A . H34E H 0.3352 -0.0059 -0.3695 0.061 Uiso 1 1 calc R . . H34F H 0.4575 -0.0359 -0.3526 0.061 Uiso 1 1 calc R . . C35' C 0.41112(14) 0.16363(11) -0.47987(10) 0.0404(3) Uani 1 1 d . . . H35A H 0.4340 0.2199 -0.4867 0.061 Uiso 1 1 calc R A . H35B H 0.3284 0.1565 -0.4698 0.061 Uiso 1 1 calc R . . H35C H 0.4448 0.1583 -0.5323 0.061 Uiso 1 1 calc R . . C36' C 0.75633(13) 0.12024(12) -0.38075(13) 0.0472(4) Uani 1 1 d . . . H36A H 0.7414 0.0603 -0.3387 0.071 Uiso 1 1 calc R A . H36B H 0.7980 0.1507 -0.3587 0.071 Uiso 1 1 calc R . . H36C H 0.8016 0.1247 -0.4351 0.071 Uiso 1 1 calc R . . C37' C 0.66748(14) 0.24890(10) -0.47147(10) 0.0397(3) Uani 1 1 d . . . H37A H 0.7022 0.2449 -0.5244 0.060 Uiso 1 1 calc R A . H37B H 0.7191 0.2830 -0.4599 0.060 Uiso 1 1 calc R . . H37C H 0.5961 0.2758 -0.4783 0.060 Uiso 1 1 calc R . . O1W O 0.8458(5) 0.1534(4) -0.6108(4) 0.0643(15) Uiso 0.25 1 d P . . H7'N H 0.3927(15) 0.1344(12) -0.1836(12) 0.038(5) Uiso 1 1 d . . . H7N H 0.7416(15) -0.1204(11) 0.0242(11) 0.036(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0238(5) 0.0234(5) 0.0262(5) -0.0120(4) -0.0033(4) 0.0055(4) C1 0.0229(5) 0.0257(6) 0.0250(5) -0.0130(5) -0.0060(4) 0.0064(4) N2 0.0296(5) 0.0236(5) 0.0252(5) -0.0121(4) -0.0049(4) 0.0076(4) C2 0.0237(5) 0.0223(5) 0.0258(5) -0.0118(4) -0.0063(4) 0.0049(4) N3 0.0289(5) 0.0215(5) 0.0245(5) -0.0107(4) -0.0045(4) 0.0054(4) C3 0.0279(6) 0.0242(6) 0.0251(6) -0.0121(5) -0.0069(5) 0.0053(4) N4 0.0347(6) 0.0210(5) 0.0273(5) -0.0105(4) -0.0026(4) 0.0067(4) C4 0.0393(7) 0.0232(6) 0.0301(6) -0.0130(5) -0.0062(5) 0.0098(5) C5 0.0477(9) 0.0340(8) 0.0577(10) -0.0272(7) -0.0113(8) 0.0085(6) C6 0.0676(12) 0.0324(8) 0.0644(11) -0.0306(8) -0.0108(9) 0.0118(8) C7 0.0662(11) 0.0339(8) 0.0418(8) -0.0188(7) -0.0045(8) 0.0226(8) C8 0.0454(9) 0.0426(9) 0.0485(9) -0.0193(7) -0.0081(7) 0.0201(7) C9 0.0422(8) 0.0317(7) 0.0398(8) -0.0170(6) -0.0107(6) 0.0123(6) C10 0.0335(6) 0.0219(6) 0.0307(6) -0.0125(5) -0.0027(5) 0.0006(5) C11 0.0410(8) 0.0283(7) 0.0325(7) -0.0106(5) -0.0058(6) -0.0012(5) C12 0.0585(10) 0.0348(8) 0.0339(8) -0.0089(6) -0.0009(7) -0.0084(7) C13 0.0546(10) 0.0376(9) 0.0501(10) -0.0159(7) 0.0169(8) -0.0102(7) C14 0.0375(8) 0.0338(8) 0.0662(11) -0.0171(8) 0.0078(8) -0.0003(6) C15 0.0344(7) 0.0270(7) 0.0455(8) -0.0108(6) -0.0031(6) 0.0023(5) O1 0.0308(5) 0.0260(4) 0.0276(4) -0.0127(4) 0.0010(4) 0.0082(4) C16 0.0273(6) 0.0310(6) 0.0326(6) -0.0176(5) -0.0029(5) 0.0103(5) C17 0.0317(6) 0.0393(7) 0.0357(7) -0.0228(6) -0.0084(5) 0.0127(5) C18 0.0318(6) 0.0334(7) 0.0313(6) -0.0198(5) -0.0083(5) 0.0096(5) C19 0.0398(7) 0.0365(7) 0.0310(7) -0.0156(6) -0.0031(6) 0.0070(6) C20 0.0485(9) 0.0287(7) 0.0371(7) -0.0127(6) -0.0051(6) 0.0081(6) C21 0.0404(7) 0.0313(7) 0.0370(7) -0.0198(6) -0.0062(6) 0.0110(6) C22 0.0302(6) 0.0307(6) 0.0301(6) -0.0176(5) -0.0076(5) 0.0085(5) N5 0.0304(5) 0.0306(6) 0.0311(5) -0.0175(5) -0.0072(4) 0.0089(4) C23 0.0320(6) 0.0372(7) 0.0294(6) -0.0172(6) -0.0080(5) 0.0100(5) C24 0.0406(8) 0.0349(7) 0.0339(7) -0.0171(6) -0.0085(6) 0.0039(6) C25 0.0510(10) 0.0427(9) 0.0400(9) -0.0112(7) -0.0048(7) -0.0013(7) C26 0.0513(11) 0.0655(13) 0.0413(9) -0.0108(9) 0.0082(8) 0.0085(9) C27 0.0586(12) 0.0655(13) 0.0435(10) -0.0157(9) 0.0089(8) 0.0270(10) N6 0.0497(8) 0.0481(8) 0.0375(7) -0.0155(6) 0.0015(6) 0.0226(7) N7 0.0285(5) 0.0214(5) 0.0259(5) -0.0104(4) 0.0007(4) 0.0058(4) C29 0.0247(5) 0.0217(5) 0.0255(5) -0.0125(4) -0.0023(4) 0.0036(4) C30 0.0240(5) 0.0232(5) 0.0300(6) -0.0143(5) -0.0062(5) 0.0053(4) C31 0.0320(6) 0.0263(6) 0.0257(6) -0.0135(5) -0.0077(5) 0.0095(5) N8 0.0244(5) 0.0303(6) 0.0366(6) -0.0171(5) 0.0002(4) 0.0063(4) O2 0.0329(6) 0.0517(7) 0.0587(7) -0.0307(6) 0.0137(5) 0.0045(5) C32 0.0245(6) 0.0430(8) 0.0580(9) -0.0336(8) -0.0043(6) 0.0013(5) C33 0.0296(7) 0.0498(9) 0.0454(8) -0.0336(7) -0.0095(6) 0.0040(6) C34 0.0289(8) 0.0977(17) 0.0949(16) -0.0665(15) -0.0207(9) 0.0098(9) C35 0.0373(8) 0.0366(8) 0.0846(14) -0.0304(9) 0.0124(9) -0.0069(7) C36 0.0596(10) 0.0406(8) 0.0290(7) -0.0161(6) -0.0147(7) 0.0181(7) C37 0.0433(8) 0.0342(7) 0.0449(8) -0.0268(6) -0.0119(6) 0.0134(6) N1' 0.0290(9) 0.0243(8) 0.0219(7) -0.0109(6) -0.0040(7) 0.0076(7) C1' 0.0278(9) 0.0278(8) 0.0235(8) -0.0134(7) -0.0038(7) 0.0078(7) N2' 0.0280(8) 0.0241(7) 0.0227(7) -0.0104(6) -0.0021(6) 0.0076(6) C3' 0.0255(12) 0.0250(10) 0.0219(9) -0.0113(7) -0.0047(9) 0.0073(9) N3' 0.0248(13) 0.0208(10) 0.0229(8) -0.0098(7) -0.0033(9) 0.0046(9) C2' 0.0241(17) 0.0252(11) 0.0248(10) -0.0130(8) -0.0042(13) 0.0078(13) N4' 0.0414(6) 0.0250(5) 0.0216(5) -0.0081(4) -0.0010(4) 0.0138(5) C4' 0.0389(7) 0.0226(6) 0.0250(6) -0.0060(5) 0.0012(5) 0.0114(5) C5' 0.0455(9) 0.0389(8) 0.0398(8) -0.0142(7) -0.0091(7) 0.0136(7) C6' 0.0494(10) 0.0558(11) 0.0458(9) -0.0132(8) -0.0107(8) 0.0287(8) C7' 0.0705(12) 0.0326(8) 0.0363(8) -0.0071(6) 0.0050(8) 0.0255(8) C8' 0.0661(11) 0.0310(8) 0.0423(8) -0.0174(7) 0.0060(8) 0.0094(7) C9' 0.0449(8) 0.0332(7) 0.0396(8) -0.0176(6) 0.0003(6) 0.0077(6) C10' 0.0352(7) 0.0315(7) 0.0213(5) -0.0086(5) -0.0020(5) 0.0137(5) C11' 0.0421(8) 0.0350(8) 0.0325(7) -0.0049(6) -0.0003(6) 0.0106(6) C12' 0.0523(10) 0.0479(10) 0.0335(8) 0.0033(7) 0.0088(7) 0.0182(8) C13' 0.0787(14) 0.0722(14) 0.0241(7) -0.0100(8) 0.0020(8) 0.0406(11) C14' 0.0872(15) 0.0650(12) 0.0353(8) -0.0297(9) -0.0160(9) 0.0361(11) C15' 0.0547(10) 0.0414(8) 0.0320(7) -0.0183(6) -0.0086(7) 0.0145(7) O1' 0.0398(8) 0.0323(7) 0.0238(6) -0.0098(5) 0.0011(5) 0.0168(6) C16' 0.0331(9) 0.0339(10) 0.0292(8) -0.0135(7) 0.0001(7) 0.0098(7) C17' 0.0340(9) 0.0403(10) 0.0350(9) -0.0193(8) 0.0019(8) 0.0075(8) C18' 0.0340(9) 0.0332(9) 0.0312(9) -0.0175(7) -0.0009(7) 0.0059(7) C19' 0.0455(11) 0.0354(10) 0.0321(10) -0.0115(8) -0.0009(9) 0.0023(9) C20' 0.0472(13) 0.0279(12) 0.0378(15) -0.0108(10) -0.0102(12) 0.0100(9) C21' 0.0286(14) 0.0253(13) 0.0361(17) -0.0130(12) -0.0010(12) 0.0068(10) C22' 0.0299(14) 0.0324(12) 0.0323(12) -0.0210(9) -0.0045(10) 0.0083(10) N5' 0.0298(8) 0.0314(8) 0.0281(7) -0.0158(6) -0.0003(6) 0.0081(6) C23' 0.0308(6) 0.0395(7) 0.0340(7) -0.0221(6) -0.0005(5) 0.0043(5) C24' 0.0434(8) 0.0381(8) 0.0366(8) -0.0167(6) -0.0014(6) 0.0012(6) C25' 0.0571(11) 0.0538(11) 0.0398(9) -0.0146(8) 0.0036(8) -0.0118(9) C26' 0.0511(11) 0.0837(16) 0.0427(10) -0.0286(10) 0.0130(8) -0.0138(10) C27' 0.0413(9) 0.0849(15) 0.0520(10) -0.0448(11) 0.0087(8) 0.0022(9) N6' 0.0354(6) 0.0550(8) 0.0445(7) -0.0332(7) 0.0002(6) 0.0092(6) N7' 0.0345(6) 0.0254(5) 0.0215(5) -0.0113(4) -0.0033(4) 0.0119(4) C29' 0.0255(5) 0.0244(5) 0.0229(5) -0.0119(4) -0.0027(4) 0.0070(4) C30' 0.0254(6) 0.0273(6) 0.0301(6) -0.0141(5) -0.0037(5) 0.0035(5) C31' 0.0242(6) 0.0277(6) 0.0352(7) -0.0149(5) 0.0005(5) 0.0029(5) N8' 0.0327(6) 0.0293(6) 0.0327(6) -0.0185(5) 0.0035(5) 0.0029(4) O2' 0.0479(7) 0.0540(7) 0.0486(7) -0.0371(6) 0.0122(5) 0.0014(5) C32' 0.0313(6) 0.0297(6) 0.0257(6) -0.0144(5) 0.0001(5) -0.0003(5) C33' 0.0252(6) 0.0315(6) 0.0262(6) -0.0148(5) -0.0002(5) 0.0004(5) C34' 0.0504(9) 0.0372(8) 0.0385(8) -0.0234(6) -0.0008(7) -0.0069(7) C35' 0.0460(8) 0.0449(9) 0.0302(7) -0.0157(6) -0.0101(6) 0.0013(7) C36' 0.0281(7) 0.0532(10) 0.0616(11) -0.0294(9) -0.0039(7) 0.0123(7) C37' 0.0392(8) 0.0335(7) 0.0382(8) -0.0131(6) 0.0036(6) -0.0053(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3271(15) . ? N1 C2 1.3558(16) . ? C1 N2 1.3247(16) . ? C1 O1 1.3396(14) . ? N2 C3 1.3450(16) . ? C2 N3 1.3482(16) . ? C2 N7 1.3488(15) . ? N3 C3 1.3354(15) . ? C3 N4 1.3806(16) . ? N4 C4 1.4432(16) . ? N4 C10 1.4293(17) . ? C4 C5 1.383(2) . ? C4 C9 1.387(2) . ? C5 H5 0.9500 . ? C5 C6 1.389(2) . ? C6 H6 0.9500 . ? C6 C7 1.380(3) . ? C7 H7 0.9500 . ? C7 C8 1.379(3) . ? C8 H8 0.9500 . ? C8 C9 1.389(2) . ? C9 H9 0.9500 . ? C10 C11 1.398(2) . ? C10 C15 1.387(2) . ? C11 H11 0.9500 . ? C11 C12 1.389(2) . ? C12 H12 0.9500 . ? C12 C13 1.368(3) . ? C13 H13 0.9500 . ? C13 C14 1.392(3) . ? C14 H14 0.9500 . ? C14 C15 1.397(2) . ? C15 H15 0.9500 . ? O1 C16 1.4481(15) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.524(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.5052(18) . ? C18 C19 1.390(2) . ? C18 N5 1.3447(18) . ? C19 H19 0.9500 . ? C19 C20 1.386(2) . ? C20 H20 0.9500 . ? C20 C21 1.381(2) . ? C21 H21 0.9500 . ? C21 C22 1.3961(19) . ? C22 N5 1.3487(16) . ? C22 C23 1.4851(19) . ? C23 C24 1.394(2) . ? C23 N6 1.3380(18) . ? C24 H24 0.9500 . ? C24 C25 1.383(2) . ? C25 H25 0.9500 . ? C25 C26 1.381(3) . ? C26 H26 0.9500 . ? C26 C27 1.385(3) . ? C27 H27 0.9500 . ? C27 N6 1.333(2) . ? N7 C29 1.4568(15) . ? N7 H7N 0.886(17) . ? C29 H29 1.0000 . ? C29 C30 1.5245(17) . ? C29 C33 1.5210(18) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C30 C31 1.5249(17) . ? C31 N8 1.4911(18) . ? C31 C36 1.5305(19) . ? C31 C37 1.5331(19) . ? N8 O2 1.2844(15) . ? N8 C32 1.4868(19) . ? C32 C33 1.531(2) . ? C32 C34 1.524(2) . ? C32 C35 1.545(2) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? N1' C1' 1.330(2) . ? N1' C2' 1.347(6) . ? C1' N2' 1.323(2) . ? C1' O1' 1.343(2) . ? N2' C3' 1.349(3) . ? C3' N3' 1.338(4) . ? C3' N4' 1.362(3) . ? N3' C2' 1.346(7) . ? C2' N7' 1.364(5) . ? N1" C1" 1.307(8) . ? N1" C2" 1.39(2) . ? C1" N2" 1.334(8) . ? C1" O1" 1.351(7) . ? N2" C3" 1.348(13) . ? C3" N3" 1.306(17) . ? C3" N4' 1.430(11) . ? N3" C2" 1.38(2) . ? C2" N7' 1.282(18) . ? N4' C4' 1.4452(16) . ? N4' C10' 1.4325(16) . ? C4' C5' 1.380(2) . ? C4' C9' 1.382(2) . ? C5' H5' 0.9500 . ? C5' C6' 1.400(2) . ? C6' H6' 0.9500 . ? C6' C7' 1.377(3) . ? C7' H7' 0.9500 . ? C7' C8' 1.376(3) . ? C8' H8' 0.9500 . ? C8' C9' 1.387(2) . ? C9' H9' 0.9500 . ? C10' C11' 1.395(2) . ? C10' C15' 1.384(2) . ? C11' H11' 0.9500 . ? C11' C12' 1.389(2) . ? C12' H12' 0.9500 . ? C12' C13' 1.373(3) . ? C13' H13' 0.9500 . ? C13' C14' 1.392(3) . ? C14' H14' 0.9500 . ? C14' C15' 1.393(2) . ? C15' H15' 0.9500 . ? O1' C16' 1.449(2) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C16' C17' 1.511(3) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C17' C18' 1.510(3) . ? C18' C19' 1.388(3) . ? C18' N5' 1.339(2) . ? C19' H19' 0.9500 . ? C19' C20' 1.399(4) . ? C20' H20' 0.9500 . ? C20' C21' 1.397(5) . ? C21' H21' 0.9500 . ? C21' C22' 1.368(6) . ? C22' N5' 1.347(4) . ? C22' C23' 1.483(4) . ? O1" C16" 1.433(7) . ? C16" H16E 0.9900 . ? C16" H16F 0.9900 . ? C16" C17" 1.509(8) . ? C17" H17E 0.9900 . ? C17" H17F 0.9900 . ? C17" C18" 1.492(9) . ? C18" C19" 1.380(9) . ? C18" N5" 1.352(7) . ? C19" H19" 0.9500 . ? C19" C20" 1.339(14) . ? C20" H20" 0.9500 . ? C20" C21" 1.325(19) . ? C21" H21" 0.9500 . ? C21" C22" 1.50(2) . ? C22" N5" 1.331(15) . ? C22" C23' 1.506(14) . ? C23' C24' 1.396(2) . ? C23' N6' 1.3433(18) . ? C24' H24' 0.9500 . ? C24' C25' 1.381(2) . ? C25' H25' 0.9500 . ? C25' C26' 1.374(3) . ? C26' H26' 0.9500 . ? C26' C27' 1.378(3) . ? C27' H27' 0.9500 . ? C27' N6' 1.341(2) . ? N7' C29' 1.4576(15) . ? N7' H7'N 0.893(18) . ? C29' H29' 1.0000 . ? C29' C30' 1.5211(17) . ? C29' C33' 1.5185(18) . ? C30' H30C 0.9900 . ? C30' H30D 0.9900 . ? C30' C31' 1.5325(18) . ? C31' N8' 1.4959(18) . ? C31' C36' 1.528(2) . ? C31' C37' 1.537(2) . ? N8' O2' 1.2867(14) . ? N8' C32' 1.4908(18) . ? C32' C33' 1.5268(18) . ? C32' C34' 1.533(2) . ? C32' C35' 1.531(2) . ? C33' H33C 0.9900 . ? C33' H33D 0.9900 . ? C34' H34D 0.9800 . ? C34' H34E 0.9800 . ? C34' H34F 0.9800 . ? C35' H35A 0.9800 . ? C35' H35B 0.9800 . ? C35' H35C 0.9800 . ? C36' H36A 0.9800 . ? C36' H36B 0.9800 . ? C36' H36C 0.9800 . ? C37' H37A 0.9800 . ? C37' H37B 0.9800 . ? C37' H37C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 112.63(10) . . ? N1 C1 N2 128.32(11) . . ? N1 C1 O1 113.30(11) . . ? N2 C1 O1 118.36(11) . . ? C1 N2 C3 113.21(11) . . ? N1 C2 N3 125.80(11) . . ? N1 C2 N7 115.31(11) . . ? N3 C2 N7 118.90(11) . . ? C2 N3 C3 113.88(11) . . ? N2 C3 N3 126.15(11) . . ? N2 C3 N4 114.63(11) . . ? N3 C3 N4 119.20(11) . . ? C3 N4 C4 119.35(11) . . ? C3 N4 C10 124.19(11) . . ? C4 N4 C10 116.46(10) . . ? N4 C4 C5 119.04(13) . . ? N4 C4 C9 120.95(13) . . ? C5 C4 C9 119.96(14) . . ? C4 C5 H5 120.1 . . ? C4 C5 C6 119.84(17) . . ? H5 C5 C6 120.1 . . ? C5 C6 H6 119.6 . . ? C5 C6 C7 120.74(17) . . ? H6 C6 C7 119.6 . . ? C6 C7 H7 120.5 . . ? C6 C7 C8 118.93(15) . . ? H7 C7 C8 120.5 . . ? C7 C8 H8 119.4 . . ? C7 C8 C9 121.24(17) . . ? H8 C8 C9 119.4 . . ? C4 C9 C8 119.29(15) . . ? C4 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N4 C10 C11 117.71(13) . . ? N4 C10 C15 122.82(13) . . ? C11 C10 C15 119.37(13) . . ? C10 C11 H11 119.8 . . ? C10 C11 C12 120.35(15) . . ? H11 C11 C12 119.8 . . ? C11 C12 H12 119.8 . . ? C11 C12 C13 120.46(16) . . ? H12 C12 C13 119.8 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.64(16) . . ? H13 C13 C14 120.2 . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.66(16) . . ? H14 C14 C15 119.7 . . ? C10 C15 C14 119.48(15) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C1 O1 C16 117.88(10) . . ? O1 C16 H16A 109.0 . . ? O1 C16 H16B 109.0 . . ? O1 C16 C17 112.83(11) . . ? H16A C16 H16B 107.8 . . ? H16A C16 C17 109.0 . . ? H16B C16 C17 109.0 . . ? C16 C17 H17A 109.7 . . ? C16 C17 H17B 109.7 . . ? C16 C17 C18 109.83(11) . . ? H17A C17 H17B 108.2 . . ? H17A C17 C18 109.7 . . ? H17B C17 C18 109.7 . . ? C17 C18 C19 121.34(13) . . ? C17 C18 N5 116.05(12) . . ? C19 C18 N5 122.60(12) . . ? C18 C19 H19 120.8 . . ? C18 C19 C20 118.44(14) . . ? H19 C19 C20 120.8 . . ? C19 C20 H20 120.2 . . ? C19 C20 C21 119.64(14) . . ? H20 C20 C21 120.2 . . ? C20 C21 H21 120.6 . . ? C20 C21 C22 118.77(13) . . ? H21 C21 C22 120.6 . . ? C21 C22 N5 122.00(13) . . ? C21 C22 C23 121.55(12) . . ? N5 C22 C23 116.43(12) . . ? C18 N5 C22 118.54(12) . . ? C22 C23 C24 120.89(13) . . ? C22 C23 N6 116.58(13) . . ? C24 C23 N6 122.53(14) . . ? C23 C24 H24 120.5 . . ? C23 C24 C25 119.01(15) . . ? H24 C24 C25 120.5 . . ? C24 C25 H25 120.7 . . ? C24 C25 C26 118.61(16) . . ? H25 C25 C26 120.7 . . ? C25 C26 H26 120.7 . . ? C25 C26 C27 118.62(16) . . ? H26 C26 C27 120.7 . . ? C26 C27 H27 118.2 . . ? C26 C27 N6 123.57(17) . . ? H27 C27 N6 118.2 . . ? C23 N6 C27 117.63(15) . . ? C2 N7 C29 123.24(11) . . ? C2 N7 H7N 110.9(11) . . ? C29 N7 H7N 122.6(11) . . ? N7 C29 H29 109.1 . . ? N7 C29 C30 110.71(10) . . ? N7 C29 C33 111.22(11) . . ? H29 C29 C30 109.1 . . ? H29 C29 C33 109.1 . . ? C30 C29 C33 107.66(10) . . ? C29 C30 H30A 109.0 . . ? C29 C30 H30B 109.0 . . ? C29 C30 C31 113.00(10) . . ? H30A C30 H30B 107.8 . . ? H30A C30 C31 109.0 . . ? H30B C30 C31 109.0 . . ? C30 C31 N8 110.06(10) . . ? C30 C31 C36 110.90(11) . . ? C30 C31 C37 109.58(11) . . ? N8 C31 C36 109.60(12) . . ? N8 C31 C37 107.73(11) . . ? C36 C31 C37 108.90(12) . . ? C31 N8 O2 115.77(12) . . ? C31 N8 C32 124.17(10) . . ? O2 N8 C32 115.40(12) . . ? N8 C32 C33 110.82(11) . . ? N8 C32 C34 106.70(13) . . ? N8 C32 C35 108.07(14) . . ? C33 C32 C34 109.53(15) . . ? C33 C32 C35 111.10(13) . . ? C34 C32 C35 110.52(15) . . ? C29 C33 C32 113.86(12) . . ? C29 C33 H33A 108.8 . . ? C29 C33 H33B 108.8 . . ? C32 C33 H33A 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34B 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35B 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36B 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37B 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C1' N1' C2' 112.3(3) . . ? N1' C1' N2' 128.77(17) . . ? N1' C1' O1' 112.65(16) . . ? N2' C1' O1' 118.58(15) . . ? C1' N2' C3' 112.90(18) . . ? N2' C3' N3' 125.6(3) . . ? N2' C3' N4' 115.9(2) . . ? N3' C3' N4' 118.4(3) . . ? C3' N3' C2' 114.2(4) . . ? N1' C2' N3' 126.0(4) . . ? N1' C2' N7' 115.8(4) . . ? N3' C2' N7' 118.2(4) . . ? C1" N1" C2" 113.9(9) . . ? N1" C1" N2" 129.6(6) . . ? N1" C1" O1" 113.3(5) . . ? N2" C1" O1" 117.0(5) . . ? C1" N2" C3" 110.6(7) . . ? N2" C3" N3" 129.2(11) . . ? N2" C3" N4' 112.7(8) . . ? N3" C3" N4' 118.0(10) . . ? C3" N3" C2" 114.0(12) . . ? N1" C2" N3" 122.1(15) . . ? N1" C2" N7' 117.3(14) . . ? N3" C2" N7' 120.5(15) . . ? C3' N4' C3" 12.9(4) . . ? C3' N4' C4' 118.96(15) . . ? C3' N4' C10' 123.35(16) . . ? C3" N4' C4' 118.9(5) . . ? C3" N4' C10' 122.3(5) . . ? C4' N4' C10' 117.64(10) . . ? N4' C4' C5' 119.51(14) . . ? N4' C4' C9' 120.08(14) . . ? C5' C4' C9' 120.41(14) . . ? C4' C5' H5' 120.5 . . ? C4' C5' C6' 118.96(18) . . ? H5' C5' C6' 120.5 . . ? C5' C6' H6' 119.7 . . ? C5' C6' C7' 120.56(18) . . ? H6' C6' C7' 119.7 . . ? C6' C7' H7' 120.0 . . ? C6' C7' C8' 119.94(15) . . ? H7' C7' C8' 120.0 . . ? C7' C8' H8' 120.0 . . ? C7' C8' C9' 120.05(18) . . ? H8' C8' C9' 120.0 . . ? C4' C9' C8' 120.05(17) . . ? C4' C9' H9' 120.0 . . ? C8' C9' H9' 120.0 . . ? N4' C10' C11' 118.27(14) . . ? N4' C10' C15' 121.18(14) . . ? C11' C10' C15' 120.50(14) . . ? C10' C11' H11' 120.2 . . ? C10' C11' C12' 119.69(18) . . ? H11' C11' C12' 120.2 . . ? C11' C12' H12' 120.0 . . ? C11' C12' C13' 120.07(18) . . ? H12' C12' C13' 120.0 . . ? C12' C13' H13' 119.8 . . ? C12' C13' C14' 120.39(16) . . ? H13' C13' C14' 119.8 . . ? C13' C14' H14' 119.9 . . ? C13' C14' C15' 120.11(19) . . ? H14' C14' C15' 119.9 . . ? C10' C15' C14' 119.22(17) . . ? C10' C15' H15' 120.4 . . ? C14' C15' H15' 120.4 . . ? C1' O1' C16' 118.24(14) . . ? O1' C16' H16C 109.4 . . ? O1' C16' H16D 109.4 . . ? O1' C16' C17' 111.24(17) . . ? H16C C16' H16D 108.0 . . ? H16C C16' C17' 109.4 . . ? H16D C16' C17' 109.4 . . ? C16' C17' H17C 109.7 . . ? C16' C17' H17D 109.7 . . ? C16' C17' C18' 109.94(17) . . ? H17C C17' H17D 108.2 . . ? H17C C17' C18' 109.7 . . ? H17D C17' C18' 109.7 . . ? C17' C18' C19' 121.76(18) . . ? C17' C18' N5' 115.79(17) . . ? C19' C18' N5' 122.45(18) . . ? C18' C19' H19' 121.0 . . ? C18' C19' C20' 118.0(2) . . ? H19' C19' C20' 121.0 . . ? C19' C20' H20' 120.2 . . ? C19' C20' C21' 119.6(3) . . ? H20' C20' C21' 120.2 . . ? C20' C21' H21' 121.0 . . ? C20' C21' C22' 118.0(4) . . ? H21' C21' C22' 121.0 . . ? C21' C22' N5' 123.3(3) . . ? C21' C22' C23' 119.7(3) . . ? N5' C22' C23' 116.9(3) . . ? C18' N5' C22' 118.7(2) . . ? C1" O1" C16" 118.9(4) . . ? O1" C16" H16E 108.7 . . ? O1" C16" H16F 108.7 . . ? O1" C16" C17" 114.3(5) . . ? H16E C16" H16F 107.6 . . ? H16E C16" C17" 108.7 . . ? H16F C16" C17" 108.7 . . ? C16" C17" H17E 109.7 . . ? C16" C17" H17F 109.7 . . ? C16" C17" C18" 109.7(5) . . ? H17E C17" H17F 108.2 . . ? H17E C17" C18" 109.7 . . ? H17F C17" C18" 109.7 . . ? C17" C18" C19" 120.4(5) . . ? C17" C18" N5" 116.6(5) . . ? C19" C18" N5" 123.0(6) . . ? C18" C19" H19" 119.8 . . ? C18" C19" C20" 120.5(8) . . ? H19" C19" C20" 119.8 . . ? C19" C20" H20" 119.8 . . ? C19" C20" C21" 120.3(14) . . ? H20" C20" C21" 119.8 . . ? C20" C21" H21" 121.0 . . ? C20" C21" C22" 118.1(16) . . ? H21" C21" C22" 121.0 . . ? C21" C22" N5" 120.0(12) . . ? C21" C22" C23' 125.1(12) . . ? N5" C22" C23' 114.5(10) . . ? C18" N5" C22" 117.6(7) . . ? C22' C23' C22" 11.2(5) . . ? C22' C23' C24' 121.40(19) . . ? C22' C23' N6' 115.76(19) . . ? C22" C23' C24' 119.3(6) . . ? C22" C23' N6' 117.3(6) . . ? C24' C23' N6' 122.76(14) . . ? C23' C24' H24' 120.5 . . ? C23' C24' C25' 119.07(16) . . ? H24' C24' C25' 120.5 . . ? C24' C25' H25' 120.8 . . ? C24' C25' C26' 118.42(19) . . ? H25' C25' C26' 120.8 . . ? C25' C26' H26' 120.4 . . ? C25' C26' C27' 119.12(17) . . ? H26' C26' C27' 120.4 . . ? C26' C27' H27' 118.0 . . ? C26' C27' N6' 123.92(17) . . ? H27' C27' N6' 118.0 . . ? C23' N6' C27' 116.71(16) . . ? C2' N7' C2" 9.3(8) . . ? C2' N7' C29' 122.5(3) . . ? C2' N7' H7'N 114.3(12) . . ? C2" N7' C29' 123.9(8) . . ? C2" N7' H7'N 115.3(14) . . ? C29' N7' H7'N 120.1(11) . . ? N7' C29' H29' 109.1 . . ? N7' C29' C30' 111.58(10) . . ? N7' C29' C33' 109.71(10) . . ? H29' C29' C30' 109.1 . . ? H29' C29' C33' 109.1 . . ? C30' C29' C33' 108.11(10) . . ? C29' C30' H30C 109.1 . . ? C29' C30' H30D 109.1 . . ? C29' C30' C31' 112.56(11) . . ? H30C C30' H30D 107.8 . . ? H30C C30' C31' 109.1 . . ? H30D C30' C31' 109.1 . . ? C30' C31' N8' 110.41(10) . . ? C30' C31' C36' 108.97(12) . . ? C30' C31' C37' 111.74(11) . . ? N8' C31' C36' 107.48(12) . . ? N8' C31' C37' 108.78(12) . . ? C36' C31' C37' 109.36(12) . . ? C31' N8' O2' 115.84(11) . . ? C31' N8' C32' 124.80(10) . . ? O2' N8' C32' 115.62(12) . . ? N8' C32' C33' 109.68(11) . . ? N8' C32' C34' 108.04(12) . . ? N8' C32' C35' 109.35(11) . . ? C33' C32' C34' 109.07(11) . . ? C33' C32' C35' 110.92(12) . . ? C34' C32' C35' 109.73(13) . . ? C29' C33' C32' 113.81(10) . . ? C29' C33' H33C 108.8 . . ? C29' C33' H33D 108.8 . . ? C32' C33' H33C 108.8 . . ? C32' C33' H33D 108.8 . . ? H33C C33' H33D 107.7 . . ? C32' C34' H34D 109.5 . . ? C32' C34' H34E 109.5 . . ? C32' C34' H34F 109.5 . . ? H34D C34' H34E 109.5 . . ? H34D C34' H34F 109.5 . . ? H34E C34' H34F 109.5 . . ? H35A C35' H35B 109.5 . . ? H35A C35' H35C 109.5 . . ? H35A C35' C32' 109.5 . . ? H35B C35' H35C 109.5 . . ? H35B C35' C32' 109.5 . . ? H35C C35' C32' 109.5 . . ? H36A C36' H36B 109.5 . . ? H36A C36' H36C 109.5 . . ? H36A C36' C31' 109.5 . . ? H36B C36' H36C 109.5 . . ? H36B C36' C31' 109.5 . . ? H36C C36' C31' 109.5 . . ? H37A C37' H37B 109.5 . . ? H37A C37' H37C 109.5 . . ? H37A C37' C31' 109.5 . . ? H37B C37' H37C 109.5 . . ? H37B C37' C31' 109.5 . . ? H37C C37' C31' 109.5 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.630 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.064