# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p21212 _database_code_depnum_ccdc_archive 'CCDC 879849' #TrackingRef 'web_deposit_cif_file_0_JingchaoFeng_1335946458.P21212.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 Br2 N3 O3' _chemical_formula_weight 549.26 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 40.74(3) _cell_length_b 9.259(6) _cell_length_c 12.727(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4801(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3288 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 17.16 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 3.405 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5792 _exptl_absorpt_correction_T_max 0.6658 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32845 _diffrn_reflns_av_R_equivalents 0.1146 _diffrn_reflns_av_sigmaI/netI 0.1311 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 24.89 _reflns_number_total 8254 _reflns_number_gt 4305 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0156P)^2^+6.3934P] 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 0.008(13) _refine_ls_number_reflns 8254 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1488 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1241 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.26936(2) 0.36413(10) 0.78421(7) 0.0590(3) Uani 1 1 d . . . Br2 Br 0.30737(3) -0.13414(13) -0.00431(8) 0.0826(4) Uani 1 1 d . . . Br3 Br 1.02998(3) 0.22396(18) -0.33293(9) 0.1100(5) Uani 1 1 d . . . Br4 Br 0.92574(3) 0.00426(16) 0.46324(10) 0.1076(5) Uani 1 1 d . . . C1 C 0.3510(2) 0.1671(8) 0.5775(6) 0.039(2) Uani 1 1 d . . . C2 C 0.3596(2) 0.2186(9) 0.6741(8) 0.058(3) Uani 1 1 d . . . H2 H 0.3812 0.2157 0.6969 0.070 Uiso 1 1 calc R . . C3 C 0.3349(2) 0.2754(9) 0.7374(7) 0.050(2) Uani 1 1 d . . . H3 H 0.3401 0.3121 0.8033 0.060 Uiso 1 1 calc R . . C4 C 0.3026(2) 0.2777(8) 0.7026(6) 0.044(2) Uani 1 1 d . . . C5 C 0.2943(2) 0.2179(9) 0.6046(6) 0.043(2) Uani 1 1 d . . . H5 H 0.2726 0.2150 0.5820 0.052 Uiso 1 1 calc R . . C6 C 0.3187(2) 0.1646(8) 0.5438(6) 0.036(2) Uani 1 1 d . . . C7 C 0.31714(19) 0.0909(8) 0.4372(6) 0.039(2) Uani 1 1 d . . . C8 C 0.3539(2) 0.0479(9) 0.4205(8) 0.046(2) Uani 1 1 d . . . C9 C 0.40726(17) 0.0812(10) 0.5104(8) 0.066(3) Uani 1 1 d . . . H9A H 0.4160 0.0533 0.4435 0.099 Uiso 1 1 calc R . . H9B H 0.4117 0.0068 0.5611 0.099 Uiso 1 1 calc R . . H9C H 0.4174 0.1697 0.5328 0.099 Uiso 1 1 calc R . . C10 C 0.30607(18) 0.1921(9) 0.3520(6) 0.037(2) Uani 1 1 d . . . C11 C 0.29532(19) 0.3309(9) 0.3626(6) 0.046(2) Uani 1 1 d . . . H11 H 0.2951 0.3828 0.4252 0.055 Uiso 1 1 calc R . . C12 C 0.28819(18) 0.2769(10) 0.1931(7) 0.046(2) Uani 1 1 d . . . C13 C 0.2811(2) 0.2756(11) 0.0883(7) 0.064(3) Uani 1 1 d . . . H13 H 0.2725 0.3577 0.0565 0.077 Uiso 1 1 calc R . . C14 C 0.2865(2) 0.1543(12) 0.0300(7) 0.062(3) Uani 1 1 d . . . H14 H 0.2813 0.1530 -0.0411 0.074 Uiso 1 1 calc R . . C15 C 0.3000(2) 0.0317(10) 0.0779(7) 0.051(2) Uani 1 1 d . . . C16 C 0.30788(18) 0.0310(9) 0.1845(6) 0.041(2) Uani 1 1 d . . . H16 H 0.3165 -0.0510 0.2162 0.049 Uiso 1 1 calc R . . C17 C 0.30248(17) 0.1545(8) 0.2414(6) 0.0346(19) Uani 1 1 d . . . C18 C 0.2717(2) 0.5263(9) 0.2490(7) 0.069(3) Uani 1 1 d . . . H18A H 0.2730 0.5825 0.3122 0.104 Uiso 1 1 calc R . . H18B H 0.2493 0.5183 0.2272 0.104 Uiso 1 1 calc R . . H18C H 0.2843 0.5726 0.1947 0.104 Uiso 1 1 calc R . . C19 C 0.2987(2) -0.1563(11) 0.4927(7) 0.056(2) Uani 1 1 d . . . C20 C 0.3316(3) -0.2612(10) 0.6348(8) 0.067(3) Uani 1 1 d . . . C21 C 0.3619(3) -0.2050(12) 0.6870(9) 0.115(5) Uani 1 1 d . . . H21A H 0.3799 -0.2096 0.6387 0.172 Uiso 1 1 calc R . . H21B H 0.3667 -0.2628 0.7477 0.172 Uiso 1 1 calc R . . H21C H 0.3584 -0.1067 0.7081 0.172 Uiso 1 1 calc R . . C22 C 0.3377(3) -0.4004(10) 0.5760(10) 0.107(4) Uani 1 1 d . . . H22A H 0.3502 -0.3806 0.5138 0.161 Uiso 1 1 calc R . . H22B H 0.3171 -0.4431 0.5568 0.161 Uiso 1 1 calc R . . H22C H 0.3497 -0.4660 0.6202 0.161 Uiso 1 1 calc R . . C23 C 0.3036(3) -0.2702(13) 0.7108(9) 0.112(4) Uani 1 1 d . . . H23A H 0.3095 -0.3328 0.7679 0.168 Uiso 1 1 calc R . . H23B H 0.2846 -0.3078 0.6756 0.168 Uiso 1 1 calc R . . H23C H 0.2988 -0.1755 0.7376 0.168 Uiso 1 1 calc R . . C24 C 0.9422(2) 0.3369(10) -0.1181(8) 0.053(2) Uani 1 1 d . . . C25 C 0.9450(2) 0.4080(11) -0.2138(9) 0.069(3) Uani 1 1 d . . . H25 H 0.9300 0.4783 -0.2342 0.083 Uiso 1 1 calc R . . C26 C 0.9711(3) 0.3696(13) -0.2775(8) 0.082(3) Uani 1 1 d . . . H26 H 0.9734 0.4140 -0.3427 0.098 Uiso 1 1 calc R . . C27 C 0.9938(2) 0.2672(13) -0.2469(9) 0.076(3) Uani 1 1 d . . . C28 C 0.9910(2) 0.1992(10) -0.1486(7) 0.061(3) Uani 1 1 d . . . H28 H 1.0066 0.1331 -0.1257 0.073 Uiso 1 1 calc R . . C29 C 0.9644(2) 0.2339(9) -0.0874(6) 0.043(2) Uani 1 1 d . . . C30 C 0.95475(19) 0.1773(9) 0.0187(7) 0.048(2) Uani 1 1 d . . . C31 C 0.9212(2) 0.2535(10) 0.0360(8) 0.054(2) Uani 1 1 d . . . C32 C 0.8900(2) 0.4515(9) -0.0509(8) 0.073(3) Uani 1 1 d . . . H32A H 0.8975 0.5486 -0.0397 0.109 Uiso 1 1 calc R . . H32B H 0.8740 0.4271 0.0014 0.109 Uiso 1 1 calc R . . H32C H 0.8803 0.4441 -0.1195 0.109 Uiso 1 1 calc R . . C33 C 0.9782(2) 0.2218(10) 0.1025(7) 0.049(2) Uani 1 1 d . . . C34 C 1.0052(2) 0.3023(10) 0.0932(7) 0.059(3) Uani 1 1 d . . . H34 H 1.0130 0.3390 0.0300 0.070 Uiso 1 1 calc R . . C35 C 1.0007(3) 0.2568(10) 0.2611(8) 0.060(3) Uani 1 1 d . . . C36 C 1.0051(3) 0.2502(12) 0.3725(8) 0.077(3) Uani 1 1 d . . . H36 H 1.0229 0.2953 0.4045 0.092 Uiso 1 1 calc R . . C37 C 0.9822(3) 0.1749(14) 0.4316(9) 0.093(4) Uani 1 1 d . . . H37 H 0.9840 0.1695 0.5043 0.111 Uiso 1 1 calc R . . C38 C 0.9562(2) 0.1069(12) 0.3784(9) 0.071(3) Uani 1 1 d . . . C39 C 0.9515(2) 0.1154(11) 0.2733(8) 0.061(3) Uani 1 1 d . . . H39 H 0.9334 0.0714 0.2421 0.073 Uiso 1 1 calc R . . C40 C 0.9743(2) 0.1916(10) 0.2124(8) 0.053(2) Uani 1 1 d . . . C41 C 1.0504(2) 0.4047(11) 0.2050(9) 0.082(3) Uani 1 1 d . . . H41A H 1.0460 0.4899 0.2456 0.123 Uiso 1 1 calc R . . H41B H 1.0593 0.4320 0.1380 0.123 Uiso 1 1 calc R . . H41C H 1.0660 0.3453 0.2417 0.123 Uiso 1 1 calc R . . C42 C 0.9271(2) -0.0609(13) -0.0243(9) 0.064(3) Uani 1 1 d . . . C43 C 0.8813(3) -0.0231(12) -0.1480(9) 0.075(3) Uani 1 1 d . . . C44 C 0.8755(3) 0.0978(13) -0.2245(10) 0.116(5) Uani 1 1 d . . . H44A H 0.8728 0.1868 -0.1867 0.175 Uiso 1 1 calc R . . H44B H 0.8560 0.0783 -0.2644 0.175 Uiso 1 1 calc R . . H44C H 0.8939 0.1055 -0.2711 0.175 Uiso 1 1 calc R . . C45 C 0.8839(3) -0.1624(12) -0.2030(10) 0.113(4) Uani 1 1 d . . . H45A H 0.8636 -0.1828 -0.2384 0.169 Uiso 1 1 calc R . . H45B H 0.8884 -0.2374 -0.1531 0.169 Uiso 1 1 calc R . . H45C H 0.9014 -0.1577 -0.2535 0.169 Uiso 1 1 calc R . . C46 C 0.8558(3) -0.0224(14) -0.0603(11) 0.120(5) Uani 1 1 d . . . H46A H 0.8543 0.0728 -0.0308 0.179 Uiso 1 1 calc R . . H46B H 0.8622 -0.0895 -0.0065 0.179 Uiso 1 1 calc R . . H46C H 0.8348 -0.0501 -0.0882 0.179 Uiso 1 1 calc R . . N1 N 0.37176(15) 0.1022(7) 0.5013(6) 0.0452(17) Uani 1 1 d . . . N2 N 0.28511(16) 0.3817(8) 0.2687(5) 0.0504(18) Uani 1 1 d . . . N3 N 0.29562(16) -0.0340(7) 0.4332(5) 0.0500(19) Uani 1 1 d . . . H3A H 0.2795 -0.0308 0.3896 0.060 Uiso 1 1 calc R . . N4 N 0.91788(16) 0.3521(8) -0.0435(6) 0.056(2) Uani 1 1 d . . . N5 N 1.01985(18) 0.3239(8) 0.1892(7) 0.059(2) Uani 1 1 d . . . N6 N 0.95150(16) 0.0199(8) 0.0225(5) 0.0525(19) Uani 1 1 d . . . H6 H 0.9662 -0.0266 0.0573 0.063 Uiso 1 1 calc R . . O1 O 0.36482(14) -0.0200(7) 0.3480(5) 0.0615(18) Uani 1 1 d . . . O2 O 0.28052(15) -0.2588(7) 0.4844(5) 0.075(2) Uani 1 1 d . . . O3 O 0.32434(13) -0.1436(6) 0.5564(4) 0.0539(15) Uani 1 1 d . . . O4 O 0.90191(14) 0.2308(7) 0.1058(5) 0.0670(19) Uani 1 1 d . . . O5 O 0.92216(18) -0.1842(8) -0.0063(7) 0.097(3) Uani 1 1 d . . . O6 O 0.91259(14) 0.0201(6) -0.0975(5) 0.0609(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0736(6) 0.0532(5) 0.0503(5) -0.0002(5) 0.0078(5) 0.0030(6) Br2 0.0876(7) 0.0930(8) 0.0672(7) -0.0319(7) -0.0074(6) 0.0019(7) Br3 0.0747(8) 0.1951(15) 0.0603(7) -0.0250(8) 0.0057(7) 0.0099(9) Br4 0.1012(9) 0.1379(11) 0.0839(9) 0.0375(9) -0.0003(8) 0.0056(9) C1 0.036(5) 0.042(6) 0.038(5) -0.002(4) -0.006(5) -0.006(4) C2 0.050(6) 0.040(5) 0.084(8) 0.004(5) -0.017(6) 0.008(5) C3 0.066(7) 0.046(5) 0.039(5) 0.007(4) -0.009(5) -0.011(5) C4 0.046(6) 0.042(5) 0.045(5) 0.010(4) -0.006(5) 0.002(4) C5 0.038(5) 0.049(5) 0.043(5) 0.008(4) -0.012(5) -0.008(4) C6 0.035(5) 0.033(5) 0.040(5) 0.013(4) -0.005(4) -0.006(4) C7 0.049(6) 0.033(5) 0.033(5) 0.006(4) -0.012(4) -0.005(4) C8 0.040(6) 0.047(6) 0.051(6) 0.016(5) 0.002(5) 0.015(5) C9 0.019(5) 0.083(7) 0.096(8) 0.006(6) -0.009(5) 0.004(4) C10 0.027(5) 0.049(6) 0.034(5) 0.004(4) -0.001(4) 0.009(4) C11 0.045(5) 0.060(7) 0.032(5) 0.003(4) 0.000(4) 0.004(5) C12 0.025(5) 0.057(6) 0.056(6) 0.000(5) -0.001(4) 0.003(4) C13 0.069(7) 0.078(7) 0.045(6) 0.002(6) -0.014(5) 0.016(6) C14 0.062(6) 0.086(8) 0.038(5) 0.008(6) -0.005(5) 0.003(6) C15 0.045(6) 0.067(7) 0.042(6) -0.022(5) 0.009(5) -0.012(5) C16 0.035(5) 0.054(6) 0.035(5) 0.006(4) -0.004(4) 0.005(4) C17 0.030(5) 0.030(5) 0.044(5) 0.003(4) 0.000(4) 0.007(4) C18 0.086(7) 0.057(6) 0.064(7) -0.007(5) -0.001(6) 0.040(6) C19 0.041(6) 0.065(7) 0.062(6) 0.010(6) -0.023(5) -0.022(5) C20 0.079(8) 0.046(6) 0.075(7) 0.023(6) -0.028(6) -0.008(6) C21 0.107(9) 0.100(9) 0.138(11) 0.052(8) -0.086(9) -0.026(7) C22 0.127(10) 0.045(7) 0.149(12) 0.002(7) -0.044(9) 0.007(7) C23 0.168(13) 0.101(9) 0.067(7) 0.011(7) -0.008(9) -0.008(9) C24 0.037(6) 0.058(7) 0.063(7) -0.007(5) -0.007(5) 0.008(5) C25 0.043(6) 0.083(8) 0.082(8) 0.018(7) -0.012(6) 0.008(5) C26 0.050(7) 0.116(9) 0.080(7) 0.029(8) -0.006(7) -0.011(7) C27 0.022(6) 0.112(9) 0.094(9) -0.033(7) -0.002(6) -0.002(6) C28 0.071(8) 0.058(6) 0.054(6) -0.006(5) -0.009(6) 0.002(5) C29 0.036(5) 0.050(6) 0.045(6) 0.000(5) -0.006(5) 0.004(5) C30 0.037(5) 0.055(6) 0.051(6) 0.000(5) -0.014(5) 0.010(4) C31 0.043(6) 0.054(6) 0.065(7) -0.006(6) -0.013(6) 0.003(5) C32 0.055(6) 0.064(7) 0.101(8) 0.014(6) 0.009(6) 0.024(6) C33 0.037(6) 0.059(6) 0.052(6) 0.005(5) -0.005(5) 0.019(5) C34 0.052(7) 0.066(7) 0.057(6) 0.006(5) -0.016(6) 0.008(5) C35 0.060(7) 0.054(6) 0.066(7) -0.021(6) -0.008(6) 0.019(6) C36 0.070(8) 0.103(9) 0.057(7) -0.010(7) -0.024(6) 0.016(7) C37 0.089(9) 0.135(12) 0.054(7) 0.007(7) -0.003(7) 0.015(8) C38 0.061(7) 0.084(8) 0.066(8) 0.011(6) 0.000(6) 0.015(6) C39 0.047(6) 0.075(7) 0.061(7) -0.001(6) -0.014(6) 0.010(5) C40 0.030(5) 0.065(6) 0.065(7) -0.012(6) -0.008(6) 0.014(5) C41 0.052(6) 0.094(8) 0.101(9) -0.010(7) -0.023(6) -0.010(6) C42 0.050(7) 0.066(8) 0.075(8) 0.004(7) -0.011(6) 0.001(6) C43 0.058(7) 0.066(8) 0.100(9) -0.021(7) -0.033(7) 0.001(6) C44 0.076(8) 0.109(10) 0.163(12) 0.051(10) -0.068(8) -0.014(7) C45 0.125(10) 0.094(10) 0.118(10) -0.026(9) -0.065(9) 0.013(8) C46 0.084(9) 0.136(11) 0.139(12) -0.001(10) -0.023(9) -0.007(9) N1 0.039(4) 0.050(5) 0.046(5) 0.002(4) -0.004(4) -0.006(4) N2 0.055(5) 0.050(5) 0.047(5) 0.008(4) -0.003(4) 0.013(4) N3 0.056(5) 0.043(5) 0.050(5) 0.015(4) -0.020(4) -0.008(4) N4 0.043(5) 0.050(5) 0.075(5) 0.006(5) -0.008(4) 0.019(4) N5 0.039(5) 0.061(6) 0.078(6) -0.011(5) -0.016(5) 0.004(4) N6 0.042(4) 0.057(5) 0.058(5) -0.001(4) -0.016(4) 0.013(4) O1 0.053(4) 0.074(5) 0.058(4) -0.014(4) -0.001(3) 0.014(3) O2 0.075(4) 0.065(4) 0.086(5) 0.023(4) -0.038(4) -0.033(4) O3 0.061(4) 0.039(3) 0.062(4) 0.006(3) -0.023(3) -0.011(3) O4 0.049(4) 0.087(5) 0.065(4) 0.010(4) 0.011(4) 0.023(4) O5 0.107(6) 0.047(4) 0.135(7) 0.020(5) -0.039(5) -0.012(4) O6 0.051(4) 0.049(4) 0.083(5) 0.001(4) -0.024(4) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.885(8) . ? Br2 C15 1.882(8) . ? Br3 C27 1.877(9) . ? Br4 C38 1.899(10) . ? C1 C2 1.364(11) . ? C1 C6 1.383(10) . ? C1 N1 1.420(9) . ? C2 C3 1.390(11) . ? C2 H2 0.9300 . ? C3 C4 1.391(11) . ? C3 H3 0.9300 . ? C4 C5 1.406(10) . ? C5 C6 1.353(10) . ? C5 H5 0.9300 . ? C6 C7 1.521(10) . ? C7 N3 1.452(9) . ? C7 C10 1.502(10) . ? C7 C8 1.564(11) . ? C8 O1 1.202(9) . ? C8 N1 1.356(10) . ? C9 N1 1.464(9) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.365(10) . ? C10 C17 1.457(10) . ? C11 N2 1.350(9) . ? C11 H11 0.9300 . ? C12 C13 1.365(11) . ? C12 N2 1.372(10) . ? C12 C17 1.415(10) . ? C13 C14 1.364(12) . ? C13 H13 0.9300 . ? C14 C15 1.402(12) . ? C14 H14 0.9300 . ? C15 C16 1.393(10) . ? C16 C17 1.371(10) . ? C16 H16 0.9300 . ? C18 N2 1.467(10) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O2 1.208(9) . ? C19 O3 1.327(9) . ? C19 N3 1.369(10) . ? C20 C21 1.494(12) . ? C20 C23 1.497(13) . ? C20 O3 1.507(10) . ? C20 C22 1.511(13) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C29 1.371(11) . ? C24 N4 1.380(10) . ? C24 C25 1.389(13) . ? C25 C26 1.384(13) . ? C25 H25 0.9300 . ? C26 C27 1.381(14) . ? C26 H26 0.9300 . ? C27 C28 1.406(13) . ? C28 C29 1.373(11) . ? C28 H28 0.9300 . ? C29 C30 1.501(11) . ? C30 N6 1.464(10) . ? C30 C33 1.489(11) . ? C30 C31 1.553(11) . ? C31 O4 1.205(10) . ? C31 N4 1.369(11) . ? C32 N4 1.464(9) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.333(11) . ? C33 C40 1.435(12) . ? C34 N5 1.375(10) . ? C34 H34 0.9300 . ? C35 N5 1.354(11) . ? C35 C40 1.382(11) . ? C35 C36 1.430(12) . ? C36 C37 1.386(13) . ? C36 H36 0.9300 . ? C37 C38 1.407(13) . ? C37 H37 0.9300 . ? C38 C39 1.352(12) . ? C39 C40 1.400(12) . ? C39 H39 0.9300 . ? C41 N5 1.467(10) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 O5 1.181(10) . ? C42 O6 1.334(11) . ? C42 N6 1.380(11) . ? C43 C45 1.471(13) . ? C43 O6 1.484(10) . ? C43 C44 1.502(14) . ? C43 C46 1.524(14) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? N3 H3A 0.8600 . ? N6 H6 0.8600 . ? 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 C1 C6 121.9(8) . . ? C2 C1 N1 127.7(8) . . ? C6 C1 N1 110.3(7) . . ? C1 C2 C3 118.1(8) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.3(8) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.2(8) . . ? C3 C4 Br1 120.8(7) . . ? C5 C4 Br1 119.0(6) . . ? C6 C5 C4 118.3(7) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 121.1(7) . . ? C5 C6 C7 130.0(7) . . ? C1 C6 C7 108.9(7) . . ? N3 C7 C10 106.9(6) . . ? N3 C7 C6 114.5(6) . . ? C10 C7 C6 112.2(6) . . ? N3 C7 C8 111.7(6) . . ? C10 C7 C8 110.4(6) . . ? C6 C7 C8 101.2(7) . . ? O1 C8 N1 125.3(8) . . ? O1 C8 C7 126.3(8) . . ? N1 C8 C7 108.5(8) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C17 106.8(7) . . ? C11 C10 C7 127.7(7) . . ? C17 C10 C7 125.3(7) . . ? N2 C11 C10 109.8(7) . . ? N2 C11 H11 125.1 . . ? C10 C11 H11 125.1 . . ? C13 C12 N2 132.2(9) . . ? C13 C12 C17 120.4(9) . . ? N2 C12 C17 107.4(7) . . ? C12 C13 C14 120.3(9) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 119.6(8) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 121.1(8) . . ? C16 C15 Br2 120.1(7) . . ? C14 C15 Br2 118.8(7) . . ? C17 C16 C15 118.3(8) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C12 120.3(7) . . ? C16 C17 C10 133.9(7) . . ? C12 C17 C10 105.6(7) . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 C19 O3 127.3(9) . . ? O2 C19 N3 123.0(8) . . ? O3 C19 N3 109.7(8) . . ? C21 C20 C23 111.1(10) . . ? C21 C20 O3 101.8(7) . . ? C23 C20 O3 108.6(8) . . ? C21 C20 C22 112.4(10) . . ? C23 C20 C22 113.5(9) . . ? O3 C20 C22 108.7(8) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 N4 110.3(9) . . ? C29 C24 C25 121.7(9) . . ? N4 C24 C25 127.9(9) . . ? C26 C25 C24 117.1(9) . . ? C26 C25 H25 121.5 . . ? C24 C25 H25 121.5 . . ? C27 C26 C25 121.8(10) . . ? C27 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C26 C27 C28 120.2(9) . . ? C26 C27 Br3 120.5(9) . . ? C28 C27 Br3 119.2(9) . . ? C29 C28 C27 117.7(9) . . ? C29 C28 H28 121.1 . . ? C27 C28 H28 121.1 . . ? C24 C29 C28 121.4(8) . . ? C24 C29 C30 109.1(8) . . ? C28 C29 C30 129.4(8) . . ? N6 C30 C33 108.1(7) . . ? N6 C30 C29 113.6(7) . . ? C33 C30 C29 112.4(7) . . ? N6 C30 C31 111.6(7) . . ? C33 C30 C31 109.7(7) . . ? C29 C30 C31 101.4(7) . . ? O4 C31 N4 126.6(8) . . ? O4 C31 C30 126.8(9) . . ? N4 C31 C30 106.6(8) . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C40 106.7(9) . . ? C34 C33 C30 128.3(9) . . ? C40 C33 C30 124.9(9) . . ? C33 C34 N5 111.2(9) . . ? C33 C34 H34 124.4 . . ? N5 C34 H34 124.4 . . ? N5 C35 C40 110.2(8) . . ? N5 C35 C36 128.2(10) . . ? C40 C35 C36 121.6(11) . . ? C37 C36 C35 118.3(10) . . ? C37 C36 H36 120.8 . . ? C35 C36 H36 120.8 . . ? C36 C37 C38 118.1(10) . . ? C36 C37 H37 120.9 . . ? C38 C37 H37 120.9 . . ? C39 C38 C37 123.8(10) . . ? C39 C38 Br4 120.0(9) . . ? C37 C38 Br4 116.2(9) . . ? C38 C39 C40 118.9(9) . . ? C38 C39 H39 120.5 . . ? C40 C39 H39 120.5 . . ? C35 C40 C39 119.2(10) . . ? C35 C40 C33 105.4(9) . . ? C39 C40 C33 135.4(9) . . ? N5 C41 H41A 109.5 . . ? N5 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? N5 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O5 C42 O6 127.2(10) . . ? O5 C42 N6 124.2(10) . . ? O6 C42 N6 108.4(9) . . ? C45 C43 O6 112.4(9) . . ? C45 C43 C44 110.9(10) . . ? O6 C43 C44 102.4(8) . . ? C45 C43 C46 113.7(11) . . ? O6 C43 C46 105.5(8) . . ? C44 C43 C46 111.4(10) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C8 N1 C1 110.8(7) . . ? C8 N1 C9 122.8(7) . . ? C1 N1 C9 126.2(7) . . ? C11 N2 C12 110.3(7) . . ? C11 N2 C18 125.7(7) . . ? C12 N2 C18 124.0(7) . . ? C19 N3 C7 125.8(7) . . ? C19 N3 H3A 117.1 . . ? C7 N3 H3A 117.1 . . ? C31 N4 C24 111.7(7) . . ? C31 N4 C32 123.0(8) . . ? C24 N4 C32 125.1(8) . . ? C35 N5 C34 106.5(7) . . ? C35 N5 C41 129.1(9) . . ? C34 N5 C41 124.4(9) . . ? C42 N6 C30 126.2(7) . . ? C42 N6 H6 116.9 . . ? C30 N6 H6 116.9 . . ? C19 O3 C20 119.6(7) . . ? C42 O6 C43 122.1(8) . . ? 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 C6 C1 C2 C3 -2.9(12) . . . . ? N1 C1 C2 C3 -178.6(7) . . . . ? C1 C2 C3 C4 0.6(12) . . . . ? C2 C3 C4 C5 2.2(12) . . . . ? C2 C3 C4 Br1 -176.4(6) . . . . ? C3 C4 C5 C6 -2.9(11) . . . . ? Br1 C4 C5 C6 175.8(6) . . . . ? C4 C5 C6 C1 0.7(11) . . . . ? C4 C5 C6 C7 178.2(7) . . . . ? C2 C1 C6 C5 2.2(12) . . . . ? N1 C1 C6 C5 178.6(7) . . . . ? C2 C1 C6 C7 -175.7(7) . . . . ? N1 C1 C6 C7 0.7(8) . . . . ? C5 C6 C7 N3 -55.1(10) . . . . ? C1 C6 C7 N3 122.6(7) . . . . ? C5 C6 C7 C10 66.9(10) . . . . ? C1 C6 C7 C10 -115.4(7) . . . . ? C5 C6 C7 C8 -175.4(7) . . . . ? C1 C6 C7 C8 2.3(7) . . . . ? N3 C7 C8 O1 54.1(10) . . . . ? C10 C7 C8 O1 -64.7(10) . . . . ? C6 C7 C8 O1 176.3(8) . . . . ? N3 C7 C8 N1 -126.8(7) . . . . ? C10 C7 C8 N1 114.4(7) . . . . ? C6 C7 C8 N1 -4.6(7) . . . . ? N3 C7 C10 C11 120.3(8) . . . . ? C6 C7 C10 C11 -5.9(12) . . . . ? C8 C7 C10 C11 -118.0(9) . . . . ? N3 C7 C10 C17 -54.6(10) . . . . ? C6 C7 C10 C17 179.2(7) . . . . ? C8 C7 C10 C17 67.1(10) . . . . ? C17 C10 C11 N2 0.6(9) . . . . ? C7 C10 C11 N2 -175.0(7) . . . . ? N2 C12 C13 C14 -179.7(8) . . . . ? C17 C12 C13 C14 2.5(13) . . . . ? C12 C13 C14 C15 -1.2(14) . . . . ? C13 C14 C15 C16 0.4(13) . . . . ? C13 C14 C15 Br2 -179.9(7) . . . . ? C14 C15 C16 C17 -1.0(12) . . . . ? Br2 C15 C16 C17 179.3(5) . . . . ? C15 C16 C17 C12 2.3(11) . . . . ? C15 C16 C17 C10 176.8(8) . . . . ? C13 C12 C17 C16 -3.1(12) . . . . ? N2 C12 C17 C16 178.6(7) . . . . ? C13 C12 C17 C10 -178.9(8) . . . . ? N2 C12 C17 C10 2.8(8) . . . . ? C11 C10 C17 C16 -177.2(8) . . . . ? C7 C10 C17 C16 -1.4(14) . . . . ? C11 C10 C17 C12 -2.1(9) . . . . ? C7 C10 C17 C12 173.7(7) . . . . ? C29 C24 C25 C26 0.4(14) . . . . ? N4 C24 C25 C26 -177.4(9) . . . . ? C24 C25 C26 C27 -1.2(15) . . . . ? C25 C26 C27 C28 -0.4(16) . . . . ? C25 C26 C27 Br3 -177.3(8) . . . . ? C26 C27 C28 C29 2.8(14) . . . . ? Br3 C27 C28 C29 179.7(6) . . . . ? N4 C24 C29 C28 -179.8(8) . . . . ? C25 C24 C29 C28 2.0(13) . . . . ? N4 C24 C29 C30 -1.7(9) . . . . ? C25 C24 C29 C30 -179.9(8) . . . . ? C27 C28 C29 C24 -3.6(13) . . . . ? C27 C28 C29 C30 178.8(8) . . . . ? C24 C29 C30 N6 126.2(8) . . . . ? C28 C29 C30 N6 -55.9(12) . . . . ? C24 C29 C30 C33 -110.7(8) . . . . ? C28 C29 C30 C33 67.2(11) . . . . ? C24 C29 C30 C31 6.3(9) . . . . ? C28 C29 C30 C31 -175.8(8) . . . . ? N6 C30 C31 O4 50.1(12) . . . . ? C33 C30 C31 O4 -69.6(12) . . . . ? C29 C30 C31 O4 171.4(9) . . . . ? N6 C30 C31 N4 -130.1(7) . . . . ? C33 C30 C31 N4 110.2(8) . . . . ? C29 C30 C31 N4 -8.7(8) . . . . ? N6 C30 C33 C34 126.3(10) . . . . ? C29 C30 C33 C34 0.1(12) . . . . ? C31 C30 C33 C34 -111.9(10) . . . . ? N6 C30 C33 C40 -57.9(10) . . . . ? C29 C30 C33 C40 175.9(8) . . . . ? C31 C30 C33 C40 63.9(11) . . . . ? C40 C33 C34 N5 1.7(10) . . . . ? C30 C33 C34 N5 178.1(8) . . . . ? N5 C35 C36 C37 179.9(9) . . . . ? C40 C35 C36 C37 0.6(15) . . . . ? C35 C36 C37 C38 1.1(15) . . . . ? C36 C37 C38 C39 -2.7(17) . . . . ? C36 C37 C38 Br4 179.5(8) . . . . ? C37 C38 C39 C40 2.4(16) . . . . ? Br4 C38 C39 C40 -179.9(6) . . . . ? N5 C35 C40 C39 179.7(7) . . . . ? C36 C35 C40 C39 -0.9(13) . . . . ? N5 C35 C40 C33 0.3(10) . . . . ? C36 C35 C40 C33 179.7(8) . . . . ? C38 C39 C40 C35 -0.5(13) . . . . ? C38 C39 C40 C33 178.6(10) . . . . ? C34 C33 C40 C35 -1.2(10) . . . . ? C30 C33 C40 C35 -177.8(7) . . . . ? C34 C33 C40 C39 179.6(9) . . . . ? C30 C33 C40 C39 3.1(16) . . . . ? O1 C8 N1 C1 -175.6(8) . . . . ? C7 C8 N1 C1 5.3(8) . . . . ? O1 C8 N1 C9 -1.2(13) . . . . ? C7 C8 N1 C9 179.7(7) . . . . ? C2 C1 N1 C8 172.2(8) . . . . ? C6 C1 N1 C8 -3.9(9) . . . . ? C2 C1 N1 C9 -1.9(13) . . . . ? C6 C1 N1 C9 -178.1(7) . . . . ? C10 C11 N2 C12 1.2(9) . . . . ? C10 C11 N2 C18 179.7(8) . . . . ? C13 C12 N2 C11 179.5(9) . . . . ? C17 C12 N2 C11 -2.5(9) . . . . ? C13 C12 N2 C18 1.0(14) . . . . ? C17 C12 N2 C18 179.0(7) . . . . ? O2 C19 N3 C7 -178.1(8) . . . . ? O3 C19 N3 C7 0.7(12) . . . . ? C10 C7 N3 C19 175.1(8) . . . . ? C6 C7 N3 C19 -60.0(10) . . . . ? C8 C7 N3 C19 54.3(11) . . . . ? O4 C31 N4 C24 -171.7(9) . . . . ? C30 C31 N4 C24 8.5(9) . . . . ? O4 C31 N4 C32 3.4(14) . . . . ? C30 C31 N4 C32 -176.5(7) . . . . ? C29 C24 N4 C31 -4.5(10) . . . . ? C25 C24 N4 C31 173.5(9) . . . . ? C29 C24 N4 C32 -179.4(8) . . . . ? C25 C24 N4 C32 -1.4(14) . . . . ? C40 C35 N5 C34 0.7(9) . . . . ? C36 C35 N5 C34 -178.7(9) . . . . ? C40 C35 N5 C41 -179.2(8) . . . . ? C36 C35 N5 C41 1.4(15) . . . . ? C33 C34 N5 C35 -1.5(10) . . . . ? C33 C34 N5 C41 178.4(8) . . . . ? O5 C42 N6 C30 -167.5(10) . . . . ? O6 C42 N6 C30 17.7(13) . . . . ? C33 C30 N6 C42 164.2(8) . . . . ? C29 C30 N6 C42 -70.4(11) . . . . ? C31 C30 N6 C42 43.6(12) . . . . ? O2 C19 O3 C20 -5.0(14) . . . . ? N3 C19 O3 C20 176.2(7) . . . . ? C21 C20 O3 C19 179.2(9) . . . . ? C23 C20 O3 C19 -63.5(11) . . . . ? C22 C20 O3 C19 60.4(11) . . . . ? O5 C42 O6 C43 17.6(16) . . . . ? N6 C42 O6 C43 -167.7(8) . . . . ? C45 C43 O6 C42 -59.7(13) . . . . ? C44 C43 O6 C42 -178.7(9) . . . . ? C46 C43 O6 C42 64.7(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 24.89 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.482 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.075