# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global #TrackingRef 'C2OB25629K-ccdc-859158-cif.txt' #TrackingRef '- C2CC30743J_ccdc_859158_cif.txt' _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ? _publ_contact_author_email yanming@mail.sysu.edu.cn _publ_contact_author_phone ? _publ_contact_author_name 'Ming Yan' _publ_author_name 'Ming Yan' data_wwt_5.2_111203 #TrackingRef 'C2OB25629K-ccdc-859158-cif.txt' #TrackingRef '- C2CC30743J_ccdc_859158_cif.txt' _database_code_depnum_ccdc_archive 'CCDC 859158' #TrackingRef 'web_deposit_cif_file_0_Wen-TaoWei_1324276074.wwt_5.2_111203.cif' _audit_creation_date 2011-12-08 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H15 Br N4 O3' _chemical_formula_sum 'C22 H15 Br N4 O3' _chemical_formula_weight 463.29 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 9.26806(16) _cell_length_b 13.0043(2) _cell_length_c 16.2697(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1960.90(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6808 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 71.5624 _cell_measurement_theta_min 2.7137 _exptl_absorpt_coefficient_mu 3.140 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8838 _diffrn_reflns_theta_full 71.71 _diffrn_reflns_theta_max 71.71 _diffrn_reflns_theta_min 4.35 _diffrn_ambient_temperature 153(2) _diffrn_detector_area_resol_mean 8.2417 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -126.00 -80.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -42.2034 -99.0000 -180.0000 46 #__ type_ start__ end____ width___ exp.time_ 2 omega 75.00 118.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 42.2034 125.0000 -150.0000 43 #__ type_ start__ end____ width___ exp.time_ 3 omega 17.00 85.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 42.2034 57.0000 -120.0000 68 #__ type_ start__ end____ width___ exp.time_ 4 omega 34.00 59.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -30.0000 90.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega 77.00 107.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -94.0000 -120.0000 30 #__ type_ start__ end____ width___ exp.time_ 6 omega 79.00 129.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -61.0000 60.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega 68.00 177.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 15.0000 30.0000 109 #__ type_ start__ end____ width___ exp.time_ 8 omega 23.00 69.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -30.0000 -150.0000 46 #__ type_ start__ end____ width___ exp.time_ 9 omega 40.00 69.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -125.0000 -120.0000 29 #__ type_ start__ end____ width___ exp.time_ 10 omega 86.00 111.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -125.0000 -120.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega 120.00 156.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 125.0000 0.0000 36 #__ type_ start__ end____ width___ exp.time_ 12 omega 64.00 102.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -77.0000 -90.0000 38 #__ type_ start__ end____ width___ exp.time_ 13 omega 43.00 69.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -109.0000 105.0000 26 #__ type_ start__ end____ width___ exp.time_ 14 omega 74.00 104.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -94.0000 150.0000 30 #__ type_ start__ end____ width___ exp.time_ 15 omega 25.00 67.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -30.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 16 omega 27.00 55.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 100.0000 -45.0000 -150.0000 28 ; _diffrn_measurement_device_type 'Xcalibur, Onyx, Nova' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1453961000 _diffrn_orient_matrix_UB_12 0.0573554000 _diffrn_orient_matrix_UB_13 -0.0010341000 _diffrn_orient_matrix_UB_21 0.0714706000 _diffrn_orient_matrix_UB_22 -0.0908280000 _diffrn_orient_matrix_UB_23 0.0452349000 _diffrn_orient_matrix_UB_31 0.0370672000 _diffrn_orient_matrix_UB_32 -0.0500637000 _diffrn_orient_matrix_UB_33 -0.0831498000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Nova (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3528 _reflns_number_total 3690 _reflns_odcompleteness_completeness 99.02 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.308 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.061 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3690 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0272 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+1.9920P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.0853 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.02126(3) -0.05774(2) -0.74490(2) 0.02992(11) Uani 1 1 d . . . O1 O -0.5073(3) -0.33593(18) -0.83812(14) 0.0278(5) Uani 1 1 d . . . O2 O -0.5504(3) -0.2952(2) -0.66421(15) 0.0282(6) Uani 1 1 d . . . C4 C -0.3302(4) -0.2009(3) -0.7026(2) 0.0197(7) Uani 1 1 d . . . N5 N -0.3752(3) -0.0790(2) -0.81509(18) 0.0245(6) Uani 1 1 d . . . O6 O -0.6118(2) -0.1807(2) -0.82711(16) 0.0286(5) Uani 1 1 d . . . C7 C -0.3579(4) -0.1901(3) -0.8000(2) 0.0209(7) Uani 1 1 d . . . C8 C -0.1832(4) -0.3212(3) -0.6318(2) 0.0254(7) Uani 1 1 d . . . C9 C -0.4195(4) -0.2879(3) -0.6620(2) 0.0236(7) Uani 1 1 d . . . C10 C -0.3811(3) -0.0281(2) -0.7498(2) 0.0272(6) Uani 1 1 d . . . H10 H -0.3859 0.0433 -0.7494 0.033 Uiso 1 1 calc R . . C11 C -0.0928(5) -0.3725(3) -0.9044(2) 0.0313(9) Uani 1 1 d . . . H11 H -0.0665 -0.4414 -0.9018 0.038 Uiso 1 1 calc R . . C12 C -0.1974(4) -0.3342(3) -0.8514(2) 0.0249(7) Uani 1 1 d . . . H12 H -0.2407 -0.3779 -0.8135 0.030 Uiso 1 1 calc R . . C13 C -0.2872(4) -0.0513(3) -0.6042(2) 0.0280(7) Uani 1 1 d . . . C14 C -0.0273(4) -0.3077(3) -0.9612(2) 0.0311(8) Uani 1 1 d . . . H14 H 0.0427 -0.3330 -0.9968 0.037 Uiso 1 1 calc R . . C15 C -0.1773(4) -0.2295(3) -0.6777(2) 0.0217(6) Uani 1 1 d . . . C16 C -0.2380(4) -0.2313(3) -0.8545(2) 0.0208(7) Uani 1 1 d . . . C17 C -0.0432(4) -0.1848(3) -0.6887(2) 0.0269(7) Uani 1 1 d . . . C18 C -0.3801(4) -0.0924(3) -0.6699(2) 0.0226(7) Uani 1 1 d . . . C19 C -0.0631(5) -0.3685(3) -0.6003(2) 0.0352(9) Uani 1 1 d . . . H19 H -0.0703 -0.4294 -0.5706 0.042 Uiso 1 1 calc R . . N20 N -0.2189(4) -0.0202(3) -0.5510(2) 0.0388(8) Uani 1 1 d . . . C21 C -0.5008(4) -0.2448(2) -0.82376(18) 0.0227(6) Uani 1 1 d . . . N22 N -0.6415(4) -0.0734(3) -0.6095(2) 0.0394(8) Uani 1 1 d . . . N23 N -0.3284(3) -0.3526(2) -0.62362(17) 0.0253(6) Uani 1 1 d . . . C24 C 0.0812(4) -0.2309(3) -0.6576(2) 0.0349(8) Uani 1 1 d . . . H24 H 0.1709 -0.2006 -0.6658 0.042 Uiso 1 1 calc R . . C25 C -0.7476(4) -0.2295(4) -0.8505(3) 0.0374(9) Uani 1 1 d . . . H25A H -0.7368 -0.2619 -0.9032 0.056 Uiso 1 1 calc R . . H25B H -0.8222 -0.1784 -0.8535 0.056 Uiso 1 1 calc R . . H25C H -0.7732 -0.2803 -0.8102 0.056 Uiso 1 1 calc R . . C26 C -0.0668(4) -0.2053(3) -0.9645(2) 0.0289(8) Uani 1 1 d . . . H26 H -0.0220 -0.1613 -1.0016 0.035 Uiso 1 1 calc R . . C27 C 0.0697(4) -0.3223(3) -0.6144(2) 0.0382(9) Uani 1 1 d . . . H27 H 0.1529 -0.3534 -0.5943 0.046 Uiso 1 1 calc R . . C28 C -0.1727(4) -0.1681(3) -0.9128(2) 0.0253(7) Uani 1 1 d . . . H28 H -0.2009 -0.0997 -0.9169 0.030 Uiso 1 1 calc R . . C29 C -0.5289(4) -0.0874(3) -0.6370(2) 0.0289(7) Uani 1 1 d . . . C1 C -0.3741(4) -0.4396(3) -0.5728(2) 0.0376(9) Uani 1 1 d . . . H1A H -0.3365 -0.5023 -0.5954 0.056 Uiso 1 1 calc R . . H1B H -0.4776 -0.4429 -0.5716 0.056 Uiso 1 1 calc R . . H1C H -0.3383 -0.4308 -0.5178 0.056 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 0.02719(17) 0.03122(17) 0.03135(17) -0.00381(17) 0.00298(15) -0.00862(13) O1 0.0292(14) 0.0253(11) 0.0289(11) -0.0006(9) -0.0031(11) -0.0020(10) O2 0.0240(14) 0.0340(13) 0.0265(12) 0.0009(11) 0.0018(10) -0.0066(10) C4 0.0215(17) 0.0184(16) 0.0191(15) -0.0015(12) 0.0018(13) -0.0028(13) N5 0.0246(14) 0.0208(15) 0.0281(14) 0.0035(12) 0.0023(12) 0.0052(12) O6 0.0190(11) 0.0356(13) 0.0313(13) -0.0020(11) -0.0041(10) 0.0012(10) C7 0.0212(17) 0.0216(16) 0.0200(16) 0.0023(13) 0.0009(13) -0.0001(14) C8 0.0295(18) 0.0265(17) 0.0204(15) -0.0013(14) -0.0031(14) 0.0004(15) C9 0.0291(18) 0.0241(16) 0.0176(15) -0.0009(13) -0.0005(14) -0.0059(14) C10 0.0237(14) 0.0234(14) 0.0344(17) 0.0000(17) 0.0034(18) 0.0010(11) C11 0.037(2) 0.0312(19) 0.0259(17) -0.0069(15) -0.0045(16) 0.0042(16) C12 0.0265(18) 0.0265(18) 0.0218(15) 0.0021(14) -0.0003(14) 0.0018(14) C13 0.0259(16) 0.0265(17) 0.0316(17) -0.0070(16) 0.0089(14) -0.0027(15) C14 0.0280(17) 0.046(2) 0.0197(15) -0.0052(14) 0.0012(14) 0.0026(16) C15 0.0219(16) 0.0231(16) 0.0201(15) -0.0052(13) -0.0023(13) 0.0023(13) C16 0.0215(16) 0.0226(16) 0.0183(15) 0.0008(13) -0.0032(13) -0.0001(13) C17 0.0279(18) 0.0316(17) 0.0213(15) -0.0055(13) 0.0022(14) -0.0048(15) C18 0.0217(16) 0.0208(15) 0.0253(16) -0.0027(13) 0.0029(14) 0.0011(13) C19 0.036(2) 0.038(2) 0.0315(18) 0.0043(16) -0.0064(16) 0.0052(17) N20 0.0397(19) 0.0412(19) 0.0354(17) -0.0129(15) 0.0014(15) -0.0045(15) C21 0.0211(17) 0.0301(16) 0.0170(13) 0.0011(12) 0.0029(13) 0.0018(14) N22 0.0295(17) 0.0378(19) 0.0509(19) -0.0041(16) 0.0109(14) -0.0007(14) N23 0.0272(15) 0.0258(14) 0.0229(13) 0.0071(12) -0.0052(12) -0.0064(11) C24 0.0203(17) 0.052(2) 0.0325(19) -0.0028(18) -0.0010(15) -0.0001(16) C25 0.0164(16) 0.054(2) 0.042(2) -0.009(2) 0.0004(15) 0.0001(16) C26 0.0223(17) 0.042(2) 0.0225(16) 0.0012(14) 0.0013(13) -0.0080(14) C27 0.0269(18) 0.050(2) 0.037(2) 0.0018(19) -0.0097(16) 0.0082(18) C28 0.0267(17) 0.0274(17) 0.0217(15) 0.0011(14) 0.0012(13) -0.0004(14) C29 0.0284(18) 0.0282(16) 0.0302(16) -0.0010(13) 0.0007(15) -0.0007(14) C1 0.046(2) 0.0331(19) 0.0339(18) 0.0128(18) -0.0072(16) -0.0153(19) _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 C17 1.900(4) . ? O1 C21 1.210(4) . ? O2 C9 1.217(4) . ? C4 C7 1.612(4) . ? C4 C9 1.550(5) . ? C4 C15 1.520(5) . ? C4 C18 1.576(5) . ? N5 C7 1.474(5) . ? N5 C10 1.253(5) . ? O6 C21 1.324(4) . ? O6 C25 1.460(4) . ? C7 C16 1.519(5) . ? C7 C21 1.553(5) . ? C8 C15 1.408(5) . ? C8 C19 1.372(5) . ? C8 N23 1.413(5) . ? C9 N23 1.346(5) . ? C10 H10 0.9300 . ? C10 C18 1.545(5) . ? C11 H11 0.9300 . ? C11 C12 1.389(5) . ? C11 C14 1.391(6) . ? C12 H12 0.9300 . ? C12 C16 1.391(5) . ? C13 C18 1.473(5) . ? C13 N20 1.146(5) . ? C14 H14 0.9300 . ? C14 C26 1.382(5) . ? C15 C17 1.384(5) . ? C16 C28 1.393(5) . ? C17 C24 1.394(5) . ? C18 C29 1.481(5) . ? C19 H19 0.9300 . ? C19 C27 1.389(6) . ? N22 C29 1.150(5) . ? N23 C1 1.464(4) . ? C24 H24 0.9300 . ? C24 C27 1.386(6) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26 0.9300 . ? C26 C28 1.380(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 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 C9 C4 C7 113.4(3) . . ? C9 C4 C18 110.6(3) . . ? C15 C4 C7 115.6(3) . . ? C15 C4 C9 101.9(3) . . ? C15 C4 C18 113.8(3) . . ? C18 C4 C7 102.0(3) . . ? C10 N5 C7 112.4(3) . . ? C21 O6 C25 114.0(3) . . ? N5 C7 C4 105.4(3) . . ? N5 C7 C16 109.1(3) . . ? N5 C7 C21 108.3(3) . . ? C16 C7 C4 115.3(3) . . ? C16 C7 C21 108.5(3) . . ? C21 C7 C4 110.0(3) . . ? C15 C8 N23 109.4(3) . . ? C19 C8 C15 123.2(4) . . ? C19 C8 N23 127.4(4) . . ? O2 C9 C4 125.2(3) . . ? O2 C9 N23 126.1(3) . . ? N23 C9 C4 108.6(3) . . ? N5 C10 H10 122.4 . . ? N5 C10 C18 115.3(3) . . ? C18 C10 H10 122.4 . . ? C12 C11 H11 120.0 . . ? C12 C11 C14 120.0(4) . . ? C14 C11 H11 120.0 . . ? C11 C12 H12 119.6 . . ? C11 C12 C16 120.7(3) . . ? C16 C12 H12 119.6 . . ? N20 C13 C18 177.4(4) . . ? C11 C14 H14 120.2 . . ? C26 C14 C11 119.6(3) . . ? C26 C14 H14 120.2 . . ? C8 C15 C4 108.2(3) . . ? C17 C15 C4 134.4(3) . . ? C17 C15 C8 117.3(3) . . ? C12 C16 C7 121.1(3) . . ? C12 C16 C28 118.4(3) . . ? C28 C16 C7 120.5(3) . . ? C15 C17 Br1 121.6(3) . . ? C15 C17 C24 121.0(3) . . ? C24 C17 Br1 117.4(3) . . ? C10 C18 C4 101.7(3) . . ? C13 C18 C4 113.5(3) . . ? C13 C18 C10 114.7(3) . . ? C13 C18 C29 105.4(3) . . ? C29 C18 C4 115.8(3) . . ? C29 C18 C10 105.9(3) . . ? C8 C19 H19 121.2 . . ? C8 C19 C27 117.6(4) . . ? C27 C19 H19 121.2 . . ? O1 C21 O6 124.7(3) . . ? O1 C21 C7 122.6(3) . . ? O6 C21 C7 112.7(3) . . ? C8 N23 C1 123.5(3) . . ? C9 N23 C8 111.9(3) . . ? C9 N23 C1 124.4(3) . . ? C17 C24 H24 120.3 . . ? C27 C24 C17 119.3(3) . . ? C27 C24 H24 120.3 . . ? O6 C25 H25A 109.5 . . ? O6 C25 H25B 109.5 . . ? O6 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C14 C26 H26 119.9 . . ? C28 C26 C14 120.2(3) . . ? C28 C26 H26 119.9 . . ? C19 C27 H27 119.2 . . ? C24 C27 C19 121.5(3) . . ? C24 C27 H27 119.2 . . ? C16 C28 H28 119.4 . . ? C26 C28 C16 121.1(3) . . ? C26 C28 H28 119.4 . . ? N22 C29 C18 173.2(4) . . ? N23 C1 H1A 109.5 . . ? N23 C1 H1B 109.5 . . ? N23 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 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 Br1 C17 C24 C27 178.4(3) . . . . ? O2 C9 N23 C8 -179.0(3) . . . . ? O2 C9 N23 C1 -4.6(6) . . . . ? C4 C7 C16 C12 60.4(5) . . . . ? C4 C7 C16 C28 -123.9(4) . . . . ? C4 C7 C21 O1 -84.8(4) . . . . ? C4 C7 C21 O6 95.8(3) . . . . ? C4 C9 N23 C8 0.4(4) . . . . ? C4 C9 N23 C1 174.8(3) . . . . ? C4 C15 C17 Br1 0.9(5) . . . . ? C4 C15 C17 C24 179.9(4) . . . . ? C4 C18 C29 N22 177(3) . . . . ? N5 C7 C16 C12 178.8(3) . . . . ? N5 C7 C16 C28 -5.5(4) . . . . ? N5 C7 C21 O1 160.4(3) . . . . ? N5 C7 C21 O6 -19.0(4) . . . . ? N5 C10 C18 C4 14.4(4) . . . . ? N5 C10 C18 C13 137.2(3) . . . . ? N5 C10 C18 C29 -107.0(3) . . . . ? C7 C4 C9 O2 -56.8(5) . . . . ? C7 C4 C9 N23 123.7(3) . . . . ? C7 C4 C15 C8 -122.0(3) . . . . ? C7 C4 C15 C17 60.0(5) . . . . ? C7 C4 C18 C10 -16.9(3) . . . . ? C7 C4 C18 C13 -140.5(3) . . . . ? C7 C4 C18 C29 97.4(3) . . . . ? C7 N5 C10 C18 -4.1(4) . . . . ? C7 C16 C28 C26 -177.9(3) . . . . ? C8 C15 C17 Br1 -177.0(2) . . . . ? C8 C15 C17 C24 2.0(5) . . . . ? C8 C19 C27 C24 0.9(6) . . . . ? C9 C4 C7 N5 134.7(3) . . . . ? C9 C4 C7 C16 -104.8(4) . . . . ? C9 C4 C7 C21 18.2(4) . . . . ? C9 C4 C15 C8 1.4(3) . . . . ? C9 C4 C15 C17 -176.6(4) . . . . ? C9 C4 C18 C10 -137.8(3) . . . . ? C9 C4 C18 C13 98.6(3) . . . . ? C9 C4 C18 C29 -23.6(4) . . . . ? C10 N5 C7 C4 -8.0(4) . . . . ? C10 N5 C7 C16 -132.4(3) . . . . ? C10 N5 C7 C21 109.7(3) . . . . ? C10 C18 C29 N22 -72(3) . . . . ? C11 C12 C16 C7 176.7(3) . . . . ? C11 C12 C16 C28 0.9(5) . . . . ? C11 C14 C26 C28 -1.3(5) . . . . ? C12 C11 C14 C26 0.1(5) . . . . ? C12 C16 C28 C26 -2.1(5) . . . . ? C13 C18 C29 N22 50(3) . . . . ? C14 C11 C12 C16 0.1(5) . . . . ? C14 C26 C28 C16 2.3(5) . . . . ? C15 C4 C7 N5 -108.2(3) . . . . ? C15 C4 C7 C16 12.3(5) . . . . ? C15 C4 C7 C21 135.3(3) . . . . ? C15 C4 C9 O2 178.4(3) . . . . ? C15 C4 C9 N23 -1.1(3) . . . . ? C15 C4 C18 C10 108.3(3) . . . . ? C15 C4 C18 C13 -15.4(4) . . . . ? C15 C4 C18 C29 -137.5(3) . . . . ? C15 C8 C19 C27 0.6(6) . . . . ? C15 C8 N23 C9 0.5(4) . . . . ? C15 C8 N23 C1 -173.9(3) . . . . ? C15 C17 C24 C27 -0.7(5) . . . . ? C16 C7 C21 O1 42.1(4) . . . . ? C16 C7 C21 O6 -137.3(3) . . . . ? C17 C24 C27 C19 -0.8(6) . . . . ? C18 C4 C7 N5 15.8(4) . . . . ? C18 C4 C7 C16 136.2(3) . . . . ? C18 C4 C7 C21 -100.8(3) . . . . ? C18 C4 C9 O2 57.1(5) . . . . ? C18 C4 C9 N23 -122.4(3) . . . . ? C18 C4 C15 C8 120.5(3) . . . . ? C18 C4 C15 C17 -57.6(5) . . . . ? C19 C8 C15 C4 179.6(3) . . . . ? C19 C8 C15 C17 -2.0(5) . . . . ? C19 C8 N23 C9 179.6(4) . . . . ? C19 C8 N23 C1 5.2(6) . . . . ? N20 C13 C18 C4 -106(9) . . . . ? N20 C13 C18 C10 138(9) . . . . ? N20 C13 C18 C29 22(10) . . . . ? C21 C7 C16 C12 -63.4(4) . . . . ? C21 C7 C16 C28 112.3(3) . . . . ? N23 C8 C15 C4 -1.3(4) . . . . ? N23 C8 C15 C17 177.2(3) . . . . ? N23 C8 C19 C27 -178.4(4) . . . . ? C25 O6 C21 O1 -0.2(5) . . . . ? C25 O6 C21 C7 179.1(3) . . . . ?