# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Shujiang Tu' 'Jing Li' 'Hui Feng' 'Man-Su Tu' 'Bo Jiang' 'Shu-Liang Wang' _publ_contact_author_email laotu@xznu.edu.cn _publ_contact_author_name 'Shujiang Tu' data_111204f _database_code_depnum_ccdc_archive 'CCDC 868426' #TrackingRef '- 4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H29 Br Cl N7 O4' _chemical_formula_weight 654.95 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1900(9) _cell_length_b 11.9520(11) _cell_length_c 14.0640(13) _cell_angle_alpha 83.637(2) _cell_angle_beta 82.4320(10) _cell_angle_gamma 68.6670(10) _cell_volume 1577.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1008 _cell_measurement_theta_min 2.753 _cell_measurement_theta_max 19.09 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6652 _exptl_absorpt_correction_T_max 0.8247 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7532 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.2941 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5327 _reflns_number_gt 1889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1980P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.091(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5327 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2931 _refine_ls_R_factor_gt 0.1395 _refine_ls_wR_factor_ref 0.4255 _refine_ls_wR_factor_gt 0.3371 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.2808(3) 0.5023(2) 0.95406(15) 0.1307(13) Uani 1 1 d . . . Cl1 Cl 1.1500(4) 0.4001(5) 0.2250(4) 0.119(2) Uani 1 1 d . . . N1 N 0.6386(9) 0.7027(8) 0.4581(7) 0.046(3) Uani 1 1 d . . . N2 N 0.7546(9) 0.8091(8) 0.5187(6) 0.038(2) Uani 1 1 d . . . N3 N 0.8820(11) 0.9095(9) 0.5709(8) 0.062(3) Uani 1 1 d . . . H3A H 0.9540 0.8681 0.5345 0.074 Uiso 1 1 calc R . . H3B H 0.8891 0.9619 0.6052 0.074 Uiso 1 1 calc R . . N4 N 0.3925(10) 0.9918(8) 0.6967(7) 0.053(3) Uani 1 1 d . . . H4A H 0.3163 0.9760 0.6992 0.064 Uiso 1 1 calc R . . H4B H 0.3960 1.0448 0.7320 0.064 Uiso 1 1 calc R . . N5 N 0.6484(13) 1.1160(11) 0.7408(9) 0.076(4) Uani 1 1 d . . . N6 N 0.949(3) 0.143(3) 0.803(3) 0.142(9) Uani 1 1 d . . . N7 N 0.377(2) 0.1596(15) 0.0144(13) 0.111(5) Uani 1 1 d . . . O1 O 0.3484(8) 0.6293(8) 0.3880(6) 0.059(2) Uani 1 1 d . . . O2 O 0.1549(9) 0.7429(8) 0.4787(6) 0.067(3) Uani 1 1 d . . . O3 O 1.076(2) 0.032(2) 0.6889(16) 0.160(7) Uani 1 1 d . . . O4 O 0.3304(16) 0.1268(13) -0.1261(10) 0.121(5) Uani 1 1 d . . . C1 C 0.7541(13) 0.8918(11) 0.5743(9) 0.046(3) Uani 1 1 d . . . C2 C 0.6382(13) 0.9536(10) 0.6356(8) 0.044(3) Uani 1 1 d . . . C3 C 0.5072(12) 0.9333(10) 0.6370(8) 0.041(3) Uani 1 1 d . . . C4 C 0.5093(11) 0.8454(10) 0.5771(8) 0.039(3) Uani 1 1 d . . . C5 C 0.3709(12) 0.8119(11) 0.5836(8) 0.044(3) Uani 1 1 d . . . H5 H 0.2881 0.8861 0.5788 0.053 Uiso 1 1 calc R . . C6 C 0.3879(12) 0.7414(10) 0.4991(8) 0.043(3) Uani 1 1 d . . . C7 C 0.5139(12) 0.6870(11) 0.4458(9) 0.047(3) Uani 1 1 d . . . C8 C 0.6323(11) 0.7893(10) 0.5210(8) 0.040(3) Uani 1 1 d . . . C9 C 0.2859(13) 0.7107(11) 0.4616(9) 0.051(3) Uani 1 1 d . . . C10 C 0.4967(12) 0.6143(11) 0.3737(9) 0.052(3) Uani 1 1 d . . . H10A H 0.5215 0.6433 0.3092 0.063 Uiso 1 1 calc R . . H10B H 0.5556 0.5304 0.3840 0.063 Uiso 1 1 calc R . . C11 C 0.6420(13) 1.0446(13) 0.6934(10) 0.055(3) Uani 1 1 d . . . C12 C 0.3508(12) 0.7411(11) 0.6753(8) 0.045(3) Uani 1 1 d . . . C13 C 0.4649(13) 0.6632(11) 0.7245(9) 0.054(3) Uani 1 1 d . . . H13 H 0.5560 0.6609 0.7025 0.064 Uiso 1 1 calc R . . C14 C 0.4462(15) 0.5893(12) 0.8050(9) 0.059(4) Uani 1 1 d . . . H14 H 0.5236 0.5345 0.8339 0.070 Uiso 1 1 calc R . . C15 C 0.3070(17) 0.5996(13) 0.8417(10) 0.063(4) Uani 1 1 d . . . C16 C 0.1912(17) 0.6737(13) 0.7961(10) 0.071(4) Uani 1 1 d . . . H16 H 0.1004 0.6761 0.8187 0.085 Uiso 1 1 calc R . . C17 C 0.2146(13) 0.7461(12) 0.7138(9) 0.059(4) Uani 1 1 d . . . H17 H 0.1369 0.7990 0.6841 0.070 Uiso 1 1 calc R . . C18 C 0.7686(12) 0.6329(11) 0.4025(9) 0.043(3) Uani 1 1 d . . . C19 C 0.8478(13) 0.5233(12) 0.4395(10) 0.055(3) Uani 1 1 d . . . H19 H 0.8224 0.4957 0.5010 0.066 Uiso 1 1 calc R . . C20 C 0.9656(13) 0.4529(12) 0.3861(11) 0.062(4) Uani 1 1 d . . . H20 H 1.0229 0.3788 0.4120 0.075 Uiso 1 1 calc R . . C21 C 0.9979(13) 0.4932(12) 0.2940(11) 0.058(4) Uani 1 1 d . . . C22 C 0.9183(14) 0.6001(13) 0.2556(11) 0.069(4) Uani 1 1 d . . . H22 H 0.9416 0.6261 0.1930 0.083 Uiso 1 1 calc R . . C23 C 0.7998(13) 0.6719(12) 0.3107(10) 0.061(4) Uani 1 1 d . . . H23 H 0.7425 0.7460 0.2849 0.074 Uiso 1 1 calc R . . C24 C 0.989(3) 0.127(3) 0.713(3) 0.139(10) Uani 1 1 d . . . H24 H 0.9503 0.1880 0.6665 0.167 Uiso 1 1 calc R . . C25 C 0.841(3) 0.260(3) 0.832(2) 0.182(12) Uani 1 1 d . . . H25A H 0.8256 0.3171 0.7774 0.274 Uiso 1 1 calc R . . H25B H 0.8746 0.2895 0.8813 0.274 Uiso 1 1 calc R . . H25C H 0.7545 0.2481 0.8564 0.274 Uiso 1 1 calc R . . C26 C 1.004(3) 0.054(4) 0.882(3) 0.207(13) Uani 1 1 d . . . H26A H 0.9514 0.0003 0.8927 0.310 Uiso 1 1 calc R . . H26B H 0.9935 0.0940 0.9395 0.310 Uiso 1 1 calc R . . H26C H 1.1020 0.0085 0.8656 0.310 Uiso 1 1 calc R . . C27 C 0.408(3) 0.154(2) -0.0799(18) 0.134(8) Uani 1 1 d . . . H27 H 0.4873 0.1693 -0.1104 0.161 Uiso 1 1 calc R . . C28 C 0.464(3) 0.190(2) 0.0747(16) 0.156(10) Uani 1 1 d . . . H28A H 0.4867 0.1312 0.1283 0.233 Uiso 1 1 calc R . . H28B H 0.4135 0.2681 0.0980 0.233 Uiso 1 1 calc R . . H28C H 0.5504 0.1899 0.0375 0.233 Uiso 1 1 calc R . . C29 C 0.247(3) 0.146(3) 0.0641(17) 0.168(10) Uani 1 1 d . . . H29A H 0.1664 0.2090 0.0408 0.251 Uiso 1 1 calc R . . H29B H 0.2463 0.1503 0.1319 0.251 Uiso 1 1 calc R . . H29C H 0.2447 0.0692 0.0521 0.251 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 0.196(3) 0.121(2) 0.0933(16) 0.0330(12) -0.0173(14) -0.0886(18) Cl1 0.055(3) 0.115(4) 0.169(5) -0.071(3) 0.036(3) -0.005(2) N1 0.033(6) 0.040(6) 0.067(7) -0.020(5) -0.004(5) -0.010(5) N2 0.032(6) 0.033(6) 0.058(6) -0.018(5) -0.004(4) -0.020(5) N3 0.048(7) 0.061(8) 0.084(8) -0.025(6) -0.002(6) -0.024(6) N4 0.048(6) 0.040(6) 0.066(7) -0.016(5) 0.002(5) -0.008(5) N5 0.080(9) 0.065(9) 0.088(9) -0.035(7) 0.003(7) -0.026(7) N6 0.118(19) 0.17(2) 0.19(2) 0.03(2) -0.07(2) -0.110(18) N7 0.145(15) 0.115(13) 0.082(12) -0.028(9) -0.027(12) -0.047(11) O1 0.041(5) 0.061(6) 0.078(6) -0.018(5) -0.014(4) -0.016(4) O2 0.039(6) 0.078(7) 0.087(7) -0.010(5) -0.016(5) -0.021(5) O3 0.147(17) 0.153(17) 0.194(18) -0.007(15) -0.039(14) -0.063(13) O4 0.139(12) 0.122(11) 0.109(10) -0.024(8) -0.026(9) -0.044(9) C1 0.044(8) 0.041(8) 0.060(8) -0.005(7) -0.020(6) -0.018(6) C2 0.051(8) 0.033(7) 0.058(8) -0.009(6) -0.016(7) -0.020(6) C3 0.042(7) 0.034(7) 0.049(7) -0.012(6) -0.002(6) -0.013(6) C4 0.033(7) 0.036(7) 0.056(7) -0.007(6) -0.016(6) -0.015(6) C5 0.034(7) 0.043(8) 0.058(8) -0.017(6) -0.011(6) -0.009(6) C6 0.035(7) 0.044(8) 0.056(8) -0.011(6) -0.017(6) -0.013(6) C7 0.038(8) 0.042(8) 0.063(8) -0.017(6) -0.007(6) -0.012(6) C8 0.031(7) 0.037(7) 0.057(7) -0.014(6) -0.010(6) -0.013(6) C9 0.038(8) 0.049(8) 0.064(9) -0.012(7) -0.005(7) -0.012(7) C10 0.039(8) 0.050(8) 0.070(9) -0.016(7) -0.006(6) -0.015(6) C11 0.054(9) 0.050(9) 0.065(9) -0.012(7) -0.013(7) -0.018(7) C12 0.041(8) 0.042(8) 0.053(8) -0.009(6) -0.009(6) -0.012(6) C13 0.045(8) 0.055(9) 0.061(8) -0.002(7) -0.017(7) -0.014(7) C14 0.059(9) 0.061(9) 0.057(9) -0.004(7) -0.016(7) -0.020(7) C15 0.074(11) 0.068(10) 0.063(9) -0.004(7) -0.026(8) -0.036(9) C16 0.069(10) 0.070(11) 0.073(10) -0.005(8) 0.002(8) -0.028(9) C17 0.047(8) 0.061(9) 0.065(9) 0.001(7) -0.008(7) -0.017(7) C18 0.030(7) 0.036(8) 0.063(9) -0.016(6) -0.002(6) -0.010(6) C19 0.038(7) 0.047(9) 0.071(9) -0.006(7) -0.002(7) -0.005(7) C20 0.048(9) 0.040(8) 0.083(11) -0.020(8) -0.007(8) 0.008(7) C21 0.034(7) 0.036(8) 0.090(11) -0.021(8) 0.014(7) 0.001(6) C22 0.056(9) 0.052(10) 0.083(10) -0.012(8) 0.014(8) -0.003(8) C23 0.051(8) 0.045(8) 0.074(10) -0.009(7) 0.004(7) -0.002(7) C24 0.10(2) 0.17(3) 0.19(3) -0.04(3) -0.03(2) -0.09(2) C25 0.16(3) 0.18(3) 0.22(3) -0.05(3) -0.01(2) -0.08(2) C26 0.19(3) 0.21(3) 0.23(4) -0.01(3) -0.04(3) -0.07(3) C27 0.16(2) 0.15(2) 0.098(18) -0.026(15) -0.021(16) -0.051(18) C28 0.21(3) 0.13(2) 0.125(18) -0.035(15) -0.048(18) -0.038(19) C29 0.20(3) 0.19(3) 0.114(18) -0.028(17) 0.015(19) -0.07(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C15 1.905(14) . ? Cl1 C21 1.781(12) . ? N1 C7 1.386(14) . ? N1 C8 1.413(14) . ? N1 C18 1.460(14) . ? N2 C1 1.326(14) . ? N2 C8 1.346(13) . ? N3 C1 1.388(14) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C3 1.355(14) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C11 1.163(15) . ? N6 C24 1.29(3) . ? N6 C26 1.47(4) . ? N6 C25 1.48(4) . ? N7 C27 1.33(2) . ? N7 C29 1.46(3) . ? N7 C28 1.47(3) . ? O1 C9 1.422(14) . ? O1 C10 1.445(13) . ? O2 C9 1.245(13) . ? O3 C24 1.21(3) . ? O4 C27 1.23(2) . ? C1 C2 1.386(16) . ? C2 C3 1.438(16) . ? C2 C11 1.442(18) . ? C3 C4 1.411(15) . ? C4 C8 1.375(15) . ? C4 C5 1.589(16) . ? C5 C6 1.488(16) . ? C5 C12 1.495(16) . ? C5 H5 0.9800 . ? C6 C7 1.371(15) . ? C6 C9 1.399(16) . ? C7 C10 1.471(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C17 1.404(16) . ? C12 C13 1.407(16) . ? C13 C14 1.394(17) . ? C13 H13 0.9300 . ? C14 C15 1.410(18) . ? C14 H14 0.9300 . ? C15 C16 1.379(19) . ? C16 C17 1.413(18) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.352(16) . ? C18 C23 1.360(16) . ? C19 C20 1.371(16) . ? C19 H19 0.9300 . ? C20 C21 1.372(18) . ? C20 H20 0.9300 . ? C21 C22 1.339(18) . ? C22 C23 1.394(17) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 C7 N1 C8 118.2(9) . . ? C7 N1 C18 118.4(9) . . ? C8 N1 C18 123.3(9) . . ? C1 N2 C8 116.4(9) . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C3 N4 H4A 120.0 . . ? C3 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C24 N6 C26 125(4) . . ? C24 N6 C25 120(3) . . ? C26 N6 C25 116(3) . . ? C27 N7 C29 123(2) . . ? C27 N7 C28 122(2) . . ? C29 N7 C28 115.4(19) . . ? C9 O1 C10 106.6(9) . . ? N2 C1 C2 123.8(10) . . ? N2 C1 N3 115.1(11) . . ? C2 C1 N3 121.1(11) . . ? C1 C2 C3 119.6(10) . . ? C1 C2 C11 121.6(11) . . ? C3 C2 C11 118.6(11) . . ? N4 C3 C4 123.1(10) . . ? N4 C3 C2 120.8(10) . . ? C4 C3 C2 115.9(10) . . ? C8 C4 C3 118.5(10) . . ? C8 C4 C5 124.0(10) . . ? C3 C4 C5 117.4(10) . . ? C6 C5 C12 110.9(10) . . ? C6 C5 C4 106.1(9) . . ? C12 C5 C4 112.3(9) . . ? C6 C5 H5 109.1 . . ? C12 C5 H5 109.1 . . ? C4 C5 H5 109.1 . . ? C7 C6 C9 106.5(10) . . ? C7 C6 C5 124.8(10) . . ? C9 C6 C5 128.6(11) . . ? C6 C7 N1 123.2(10) . . ? C6 C7 C10 111.1(10) . . ? N1 C7 C10 125.6(10) . . ? N2 C8 C4 125.7(10) . . ? N2 C8 N1 113.7(10) . . ? C4 C8 N1 120.6(9) . . ? O2 C9 C6 132.7(12) . . ? O2 C9 O1 116.1(11) . . ? C6 C9 O1 111.2(10) . . ? O1 C10 C7 104.4(9) . . ? O1 C10 H10A 110.9 . . ? C7 C10 H10A 110.9 . . ? O1 C10 H10B 110.9 . . ? C7 C10 H10B 110.9 . . ? H10A C10 H10B 108.9 . . ? N5 C11 C2 178.3(14) . . ? C17 C12 C13 116.9(11) . . ? C17 C12 C5 120.4(11) . . ? C13 C12 C5 122.6(10) . . ? C14 C13 C12 122.2(12) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 118.4(12) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 121.7(13) . . ? C16 C15 Br1 119.7(11) . . ? C14 C15 Br1 118.5(11) . . ? C15 C16 C17 118.1(13) . . ? C15 C16 H16 121.0 . . ? C17 C16 H16 121.0 . . ? C12 C17 C16 122.4(12) . . ? C12 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C19 C18 C23 120.8(11) . . ? C19 C18 N1 118.8(11) . . ? C23 C18 N1 120.0(11) . . ? C18 C19 C20 119.9(13) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C21 119.1(12) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 121.6(12) . . ? C22 C21 Cl1 119.8(12) . . ? C20 C21 Cl1 118.7(10) . . ? C21 C22 C23 119.0(14) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C18 C23 C22 119.5(12) . . ? C18 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? O3 C24 N6 120(4) . . ? O3 C24 H24 120.0 . . ? N6 C24 H24 120.0 . . ? N6 C25 H25A 109.5 . . ? N6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O4 C27 N7 118(2) . . ? O4 C27 H27 120.9 . . ? N7 C27 H27 120.9 . . ? N7 C28 H28A 109.5 . . ? N7 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N7 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N7 C29 H29A 109.5 . . ? N7 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N7 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N2 C1 C2 2.5(17) . . . . ? C8 N2 C1 N3 179.6(10) . . . . ? N2 C1 C2 C3 -3.3(18) . . . . ? N3 C1 C2 C3 179.8(10) . . . . ? N2 C1 C2 C11 -178.8(11) . . . . ? N3 C1 C2 C11 4.3(18) . . . . ? C1 C2 C3 N4 179.5(11) . . . . ? C11 C2 C3 N4 -4.8(16) . . . . ? C1 C2 C3 C4 2.7(16) . . . . ? C11 C2 C3 C4 178.4(11) . . . . ? N4 C3 C4 C8 -178.5(10) . . . . ? C2 C3 C4 C8 -1.8(16) . . . . ? N4 C3 C4 C5 -2.1(16) . . . . ? C2 C3 C4 C5 174.7(10) . . . . ? C8 C4 C5 C6 -16.8(15) . . . . ? C3 C4 C5 C6 166.9(10) . . . . ? C8 C4 C5 C12 104.5(12) . . . . ? C3 C4 C5 C12 -71.7(13) . . . . ? C12 C5 C6 C7 -104.4(13) . . . . ? C4 C5 C6 C7 17.8(15) . . . . ? C12 C5 C6 C9 71.2(15) . . . . ? C4 C5 C6 C9 -166.6(11) . . . . ? C9 C6 C7 N1 176.1(11) . . . . ? C5 C6 C7 N1 -7.5(19) . . . . ? C9 C6 C7 C10 -2.3(14) . . . . ? C5 C6 C7 C10 174.1(11) . . . . ? C8 N1 C7 C6 -7.4(17) . . . . ? C18 N1 C7 C6 175.3(11) . . . . ? C8 N1 C7 C10 170.8(11) . . . . ? C18 N1 C7 C10 -6.5(17) . . . . ? C1 N2 C8 C4 -1.5(17) . . . . ? C1 N2 C8 N1 178.3(10) . . . . ? C3 C4 C8 N2 1.2(18) . . . . ? C5 C4 C8 N2 -175.0(10) . . . . ? C3 C4 C8 N1 -178.5(10) . . . . ? C5 C4 C8 N1 5.3(17) . . . . ? C7 N1 C8 N2 -171.8(10) . . . . ? C18 N1 C8 N2 5.3(15) . . . . ? C7 N1 C8 C4 8.0(16) . . . . ? C18 N1 C8 C4 -174.9(11) . . . . ? C7 C6 C9 O2 -173.9(14) . . . . ? C5 C6 C9 O2 10(2) . . . . ? C7 C6 C9 O1 3.9(13) . . . . ? C5 C6 C9 O1 -172.3(11) . . . . ? C10 O1 C9 O2 174.2(11) . . . . ? C10 O1 C9 C6 -4.0(13) . . . . ? C9 O1 C10 C7 2.4(12) . . . . ? C6 C7 C10 O1 -0.1(14) . . . . ? N1 C7 C10 O1 -178.4(11) . . . . ? C1 C2 C11 N5 -48(50) . . . . ? C3 C2 C11 N5 136(49) . . . . ? C6 C5 C12 C17 -88.6(13) . . . . ? C4 C5 C12 C17 152.8(11) . . . . ? C6 C5 C12 C13 88.5(13) . . . . ? C4 C5 C12 C13 -30.1(15) . . . . ? C17 C12 C13 C14 3.1(18) . . . . ? C5 C12 C13 C14 -174.0(11) . . . . ? C12 C13 C14 C15 -4.4(19) . . . . ? C13 C14 C15 C16 5(2) . . . . ? C13 C14 C15 Br1 -178.1(9) . . . . ? C14 C15 C16 C17 -4(2) . . . . ? Br1 C15 C16 C17 179.0(10) . . . . ? C13 C12 C17 C16 -2.3(18) . . . . ? C5 C12 C17 C16 175.0(12) . . . . ? C15 C16 C17 C12 3(2) . . . . ? C7 N1 C18 C19 -89.3(14) . . . . ? C8 N1 C18 C19 93.6(14) . . . . ? C7 N1 C18 C23 83.2(14) . . . . ? C8 N1 C18 C23 -94.0(14) . . . . ? C23 C18 C19 C20 3.6(18) . . . . ? N1 C18 C19 C20 176.0(11) . . . . ? C18 C19 C20 C21 -2.7(19) . . . . ? C19 C20 C21 C22 1(2) . . . . ? C19 C20 C21 Cl1 -179.2(10) . . . . ? C20 C21 C22 C23 0(2) . . . . ? Cl1 C21 C22 C23 -179.9(11) . . . . ? C19 C18 C23 C22 -2.7(19) . . . . ? N1 C18 C23 C22 -175.0(12) . . . . ? C21 C22 C23 C18 1(2) . . . . ? C26 N6 C24 O3 0(4) . . . . ? C25 N6 C24 O3 -180(2) . . . . ? C29 N7 C27 O4 -5(3) . . . . ? C28 N7 C27 O4 179.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 1.537 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.165