# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_I _database_code_depnum_ccdc_archive 'CCDC 902091' #TrackingRef 'compound-9h.cif' _chemical_name_systematic ? _chemical_name_common CJ142 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Br N O3' _chemical_formula_iupac ? _chemical_formula_weight 370.20 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P 1' _space_group_name_Hall 'P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' _cell_length_a 9.8447(7) _cell_length_b 9.9217(7) _cell_length_c 10.3511(13) _cell_angle_alpha 110.058(4) _cell_angle_beta 97.022(4) _cell_angle_gamma 115.079(3) _cell_volume 816.53(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3798 _cell_measurement_theta_min 2.4063 _cell_measurement_theta_max 20.1731 _cell_measurement_temperature 296.(2) _exptl_crystal_description prismatic _exptl_crystal_colour colourless-pink _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.531 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_correction_T_min 0.64 _exptl_absorpt_correction_T_max 0.79 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 14613 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.37 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _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. ; _reflns_number_total 5606 _reflns_number_gt 3831 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.1373 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_number_reflns 5606 _refine_ls_number_parameters 415 _refine_ls_number_restraints 3 _refine_ls_hydrogen_treatment refxyz _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.420 _refine_diff_density_min -0.484 _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 -0.009(10) 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' _computing_data_collection 'Bruker Instrument Service v2010.9.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.75932(8) 0.80347(9) 0.56862(7) 0.0849(3) Uani d . 1 . . Br Br2 1.24683(7) 1.20009(7) 1.43260(6) 0.0730(3) Uani d . 1 . . C C1 0.7857(7) 0.5240(9) 0.3966(6) 0.0536(16) Uani d . 1 . . C C2 0.8625(9) 0.6952(10) 0.4703(6) 0.0565(17) Uani d . 1 . . C C3 1.0125(8) 0.7830(9) 0.4749(7) 0.0548(16) Uani d . 1 . . H H3 1.0642 0.898 0.5219 0.066 Uiso calc R 1 . . C C4 1.0942(7) 0.7033(8) 0.4092(6) 0.0485(15) Uani d . 1 . . C C5 1.2532(9) 0.7927(10) 0.4188(8) 0.0671(19) Uani d . 1 . . H H5 1.3073 0.9078 0.4667 0.081 Uiso calc R 1 . . C C6 1.3292(9) 0.7127(12) 0.3588(10) 0.084(2) Uani d . 1 . . H H6 1.434 0.7741 0.3648 0.101 Uiso calc R 1 . . C C7 1.2536(9) 0.5430(10) 0.2896(8) 0.0709(19) Uani d . 1 . . H H7 1.308 0.49 0.2517 0.085 Uiso calc R 1 . . C C8 1.1001(8) 0.4529(9) 0.2767(7) 0.0576(16) Uani d . 1 . . H H8 1.0493 0.338 0.2279 0.069 Uiso calc R 1 . . C C9 1.0150(7) 0.5289(8) 0.3352(6) 0.0485(15) Uani d . 1 . . C C10 0.8555(7) 0.4413(9) 0.3291(7) 0.0513(15) Uani d . 1 . . C C11 0.7412(8) 0.2609(9) 0.2592(7) 0.0618(18) Uani d . 1 . . H H11 0.7871 0.2029 0.2912 0.074 Uiso calc R 1 . . C C12 0.6126(8) 0.2647(11) 0.3298(7) 0.070(2) Uani d . 1 . . H H12 0.5073 0.1832 0.2593 0.084 Uiso calc R 1 . . C C13 0.6815(8) 0.1827(9) 0.0940(7) 0.0575(16) Uani d . 1 . . C C14 0.6225(10) 0.0132(11) 0.0125(9) 0.084(2) Uani d . 1 . . H H14 0.6179 -0.0521 0.0602 0.101 Uiso calc R 1 . . C C15 0.5716(12) -0.0582(13) -0.1350(10) 0.106(3) Uani d . 1 . . H H15 0.5335 -0.1707 -0.1892 0.128 Uiso calc R 1 . . C C16 0.5792(12) 0.0461(17) -0.2020(9) 0.106(3) Uani d . 1 . . H H16 0.5472 0.0005 -0.3027 0.127 Uiso calc R 1 . . C C17 0.6293(13) 0.2039(13) -0.1287(9) 0.103(3) Uani d . 1 . . H H17 0.6311 0.269 -0.1759 0.123 Uiso calc R 1 . . C C18 0.6791(11) 0.2710(10) 0.0198(8) 0.089(3) Uani d . 1 . . H H18 0.7129 0.3828 0.0721 0.107 Uiso calc R 1 . . C C19 1.0972(7) 0.9662(8) 1.1342(6) 0.0505(15) Uani d . 1 . . C C20 1.0726(8) 1.0238(8) 1.2688(6) 0.0531(16) Uani d . 1 . . C C21 0.9221(9) 0.9453(9) 1.2736(8) 0.0624(18) Uani d . 1 . . H H21 0.9016 0.981 1.3607 0.075 Uiso calc R 1 . . C C22 0.7958(9) 0.8100(10) 1.1479(8) 0.0622(18) Uani d . 1 . . C C23 0.6396(10) 0.7217(12) 1.1512(11) 0.083(3) Uani d . 1 . . H H23 0.6187 0.7504 1.2388 0.1 Uiso calc R 1 . . C C24 0.5224(11) 0.5984(13) 1.0309(12) 0.097(3) Uani d . 1 . . H H24 0.4203 0.5466 1.0352 0.117 Uiso calc R 1 . . C C25 0.5509(10) 0.5467(12) 0.8997(11) 0.089(3) Uani d . 1 . . H H25 0.4685 0.4582 0.8179 0.107 Uiso calc R 1 . . C C26 0.6943(9) 0.6219(10) 0.8896(9) 0.0679(19) Uani d . 1 . . H H26 0.7111 0.5875 0.8005 0.081 Uiso calc R 1 . . C C27 0.8224(8) 0.7547(9) 1.0142(8) 0.0534(18) Uani d . 1 . . C C28 0.9799(7) 0.8413(7) 1.0121(6) 0.0500(15) Uani d . 1 . . C C29 1.0531(7) 0.8118(7) 0.8909(6) 0.0446(13) Uani d . 1 . . H H29 0.9954 0.8126 0.8073 0.054 Uiso calc R 1 . . C C30 1.2171(7) 0.9696(7) 0.9655(6) 0.0493(15) Uani d . 1 . . H H30 1.2989 0.9444 0.9397 0.059 Uiso calc R 1 . . C C31 1.0614(7) 0.6531(7) 0.8438(6) 0.0470(14) Uani d . 1 . . C C32 1.0479(11) 0.5671(10) 0.9243(8) 0.077(2) Uani d . 1 . . H H32 1.0307 0.605 1.0128 0.093 Uiso calc R 1 . . C C33 1.0590(12) 0.4262(10) 0.8779(10) 0.091(3) Uani d . 1 . . H H33 1.0477 0.369 0.9343 0.109 Uiso calc R 1 . . C C34 1.0862(11) 0.3702(10) 0.7513(10) 0.086(2) Uani d . 1 . . H H34 1.0963 0.2761 0.7207 0.104 Uiso calc R 1 . . C C35 1.0988(14) 0.4534(12) 0.6689(8) 0.100(3) Uani d . 1 . . H H35 1.1153 0.4144 0.5802 0.12 Uiso calc R 1 . . C C36 1.0876(11) 0.5916(10) 0.7140(7) 0.077(2) Uani d . 1 . . H H36 1.0978 0.647 0.6561 0.093 Uiso calc R 1 . . N N1 0.6344(8) 0.2257(10) 0.4636(8) 0.0804(19) Uani d . 1 . . N N2 1.2159(7) 1.1027(8) 0.9174(7) 0.0697(16) Uani d . 1 . . O O1 0.6299(5) 0.4188(7) 0.3819(5) 0.0716(13) Uani d . 1 . . O O2 0.6231(10) 0.0905(9) 0.4320(7) 0.123(3) Uani d . 1 . . O O3 0.6559(9) 0.3189(9) 0.5799(6) 0.112(2) Uani d . 1 . . O O4 1.2460(4) 1.0323(5) 1.1143(4) 0.0526(10) Uani d . 1 . . O O5 1.2214(8) 1.0802(7) 0.7980(6) 0.0957(19) Uani d . 1 . . O O6 1.2070(11) 1.2162(9) 1.0012(8) 0.116(3) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.1005(7) 0.1248(8) 0.0810(6) 0.0864(6) 0.0494(5) 0.0539(6) Br2 0.0960(6) 0.0760(5) 0.0483(4) 0.0519(4) 0.0232(4) 0.0172(3) C1 0.040(4) 0.080(5) 0.046(3) 0.031(4) 0.017(3) 0.032(3) C2 0.074(5) 0.083(5) 0.040(3) 0.055(4) 0.030(3) 0.032(3) C3 0.063(5) 0.062(4) 0.050(4) 0.035(4) 0.020(3) 0.031(3) C4 0.054(4) 0.053(4) 0.043(3) 0.027(3) 0.016(3) 0.026(3) C5 0.067(5) 0.064(4) 0.071(5) 0.030(4) 0.028(4) 0.033(4) C6 0.057(5) 0.102(7) 0.096(6) 0.038(5) 0.044(5) 0.043(6) C7 0.068(5) 0.075(5) 0.078(5) 0.039(4) 0.038(4) 0.032(4) C8 0.059(4) 0.053(4) 0.060(4) 0.028(3) 0.028(3) 0.022(3) C9 0.054(4) 0.060(4) 0.038(3) 0.031(3) 0.018(3) 0.025(3) C10 0.048(4) 0.064(4) 0.047(4) 0.027(4) 0.020(3) 0.031(3) C11 0.055(4) 0.077(5) 0.054(4) 0.027(4) 0.019(3) 0.037(4) C12 0.047(4) 0.095(6) 0.048(4) 0.017(4) 0.013(3) 0.034(4) C13 0.056(4) 0.069(4) 0.044(3) 0.029(3) 0.016(3) 0.023(3) C14 0.104(6) 0.089(6) 0.071(5) 0.060(5) 0.021(4) 0.034(5) C15 0.126(8) 0.093(6) 0.080(7) 0.078(6) 0.014(5) -0.008(5) C16 0.114(8) 0.172(11) 0.051(5) 0.091(8) 0.028(5) 0.045(7) C17 0.143(9) 0.092(7) 0.056(5) 0.049(6) 0.023(5) 0.029(5) C18 0.127(7) 0.076(5) 0.050(4) 0.037(5) 0.017(4) 0.034(4) C19 0.059(4) 0.054(4) 0.046(4) 0.034(3) 0.022(3) 0.021(3) C20 0.070(5) 0.064(4) 0.041(3) 0.045(4) 0.019(3) 0.024(3) C21 0.077(5) 0.092(5) 0.060(4) 0.060(4) 0.043(4) 0.047(4) C22 0.075(5) 0.081(5) 0.070(5) 0.054(4) 0.038(4) 0.050(4) C23 0.067(6) 0.125(7) 0.107(7) 0.055(5) 0.060(5) 0.084(6) C24 0.058(5) 0.120(8) 0.131(9) 0.038(6) 0.037(6) 0.078(7) C25 0.056(5) 0.101(6) 0.116(7) 0.028(5) 0.036(5) 0.065(6) C26 0.063(5) 0.069(5) 0.070(5) 0.032(4) 0.019(4) 0.031(4) C27 0.056(4) 0.068(5) 0.067(5) 0.041(4) 0.033(4) 0.044(4) C28 0.066(4) 0.053(4) 0.048(4) 0.041(4) 0.025(3) 0.024(3) C29 0.052(4) 0.051(3) 0.041(3) 0.032(3) 0.018(3) 0.021(3) C30 0.054(4) 0.048(4) 0.045(3) 0.026(3) 0.018(3) 0.017(3) C31 0.049(4) 0.049(4) 0.043(3) 0.026(3) 0.014(3) 0.018(3) C32 0.126(7) 0.092(5) 0.068(5) 0.077(5) 0.057(5) 0.054(4) C33 0.148(8) 0.083(6) 0.094(6) 0.083(6) 0.057(6) 0.055(5) C34 0.120(7) 0.073(5) 0.087(6) 0.069(5) 0.030(5) 0.032(5) C35 0.189(11) 0.108(7) 0.054(4) 0.118(8) 0.047(6) 0.031(5) C36 0.131(7) 0.093(6) 0.042(4) 0.081(6) 0.034(4) 0.031(4) N1 0.076(4) 0.071(5) 0.077(5) 0.014(4) 0.027(4) 0.041(4) N2 0.082(4) 0.059(4) 0.067(4) 0.031(3) 0.027(3) 0.031(3) O1 0.058(3) 0.095(4) 0.067(3) 0.039(3) 0.028(2) 0.038(3) O2 0.169(7) 0.090(5) 0.095(5) 0.034(5) 0.059(5) 0.059(4) O3 0.161(7) 0.104(5) 0.046(3) 0.050(4) 0.034(4) 0.026(3) O4 0.045(2) 0.060(3) 0.042(2) 0.023(2) 0.0146(18) 0.015(2) O5 0.137(5) 0.086(4) 0.053(3) 0.042(4) 0.027(3) 0.038(3) O6 0.206(8) 0.085(5) 0.102(5) 0.095(5) 0.072(5) 0.053(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C2 . 1.911(6) ? Br2 C20 . 1.894(7) ? C1 C10 . 1.354(9) ? C1 C2 . 1.386(10) ? C1 O1 . 1.394(8) ? C2 C3 . 1.343(9) ? C3 C4 . 1.427(9) ? C3 H3 . 0.93 ? C4 C5 . 1.405(9) ? C4 C9 . 1.411(9) ? C5 C6 . 1.361(11) ? C5 H5 . 0.93 ? C6 C7 . 1.372(11) ? C6 H6 . 0.93 ? C7 C8 . 1.351(10) ? C7 H7 . 0.93 ? C8 C9 . 1.408(9) ? C8 H8 . 0.93 ? C9 C10 . 1.416(9) ? C10 C11 . 1.483(10) ? C11 C13 . 1.527(9) ? C11 C12 . 1.544(10) ? C11 H11 . 0.98 ? C12 O1 . 1.360(9) ? C12 N1 . 1.575(10) ? C12 H12 . 0.98 ? C13 C18 . 1.353(10) ? C13 C14 . 1.399(11) ? C14 C15 . 1.362(12) ? C14 H14 . 0.93 ? C15 C16 . 1.414(15) ? C15 H15 . 0.93 ? C16 C17 . 1.307(15) ? C16 H16 . 0.93 ? C17 C18 . 1.372(11) ? C17 H17 . 0.93 ? C18 H18 . 0.93 ? C19 C28 . 1.350(8) ? C19 O4 . 1.404(7) ? C19 C20 . 1.407(8) ? C20 C21 . 1.368(9) ? C21 C22 . 1.425(11) ? C21 H21 . 0.93 ? C22 C27 . 1.404(10) ? C22 C23 . 1.423(11) ? C23 C24 . 1.337(13) ? C23 H23 . 0.93 ? C24 C25 . 1.387(12) ? C24 H24 . 0.93 ? C25 C26 . 1.326(11) ? C25 H25 . 0.93 ? C26 C27 . 1.421(10) ? C26 H26 . 0.93 ? C27 C28 . 1.427(9) ? C28 C29 . 1.525(8) ? C29 C31 . 1.522(8) ? C29 C30 . 1.542(9) ? C29 H29 . 0.98 ? C30 O4 . 1.388(7) ? C30 N2 . 1.566(9) ? C30 H30 . 0.98 ? C31 C32 . 1.363(9) ? C31 C36 . 1.379(9) ? C32 C33 . 1.371(11) ? C32 H32 . 0.93 ? C33 C34 . 1.346(12) ? C33 H33 . 0.93 ? C34 C35 . 1.359(12) ? C34 H34 . 0.93 ? C35 C36 . 1.346(11) ? C35 H35 . 0.93 ? C36 H36 . 0.93 ? N1 O3 . 1.165(9) ? N1 O2 . 1.218(9) ? N2 O5 . 1.192(7) ? N2 O6 . 1.208(8) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 C1 C2 . . 122.8(6) ? C10 C1 O1 . . 112.8(6) ? C2 C1 O1 . . 124.4(6) ? C3 C2 C1 . . 118.6(5) ? C3 C2 Br1 . . 120.8(5) ? C1 C2 Br1 . . 120.6(5) ? C2 C3 C4 . . 121.4(6) ? C2 C3 H3 . . 119.3 ? C4 C3 H3 . . 119.3 ? C5 C4 C9 . . 118.4(6) ? C5 C4 C3 . . 122.2(6) ? C9 C4 C3 . . 119.4(6) ? C6 C5 C4 . . 120.7(7) ? C6 C5 H5 . . 119.6 ? C4 C5 H5 . . 119.6 ? C5 C6 C7 . . 121.1(7) ? C5 C6 H6 . . 119.5 ? C7 C6 H6 . . 119.5 ? C8 C7 C6 . . 119.9(7) ? C8 C7 H7 . . 120.1 ? C6 C7 H7 . . 120.1 ? C7 C8 C9 . . 121.6(6) ? C7 C8 H8 . . 119.2 ? C9 C8 H8 . . 119.2 ? C8 C9 C4 . . 118.4(6) ? C8 C9 C10 . . 124.3(6) ? C4 C9 C10 . . 117.4(6) ? C1 C10 C9 . . 120.4(6) ? C1 C10 C11 . . 109.3(6) ? C9 C10 C11 . . 130.4(6) ? C10 C11 C13 . . 114.6(5) ? C10 C11 C12 . . 98.4(6) ? C13 C11 C12 . . 113.4(5) ? C10 C11 H11 . . 110.0 ? C13 C11 H11 . . 110.0 ? C12 C11 H11 . . 110.0 ? O1 C12 C11 . . 110.4(6) ? O1 C12 N1 . . 106.7(6) ? C11 C12 N1 . . 108.9(6) ? O1 C12 H12 . . 110.2 ? C11 C12 H12 . . 110.2 ? N1 C12 H12 . . 110.2 ? C18 C13 C14 . . 117.0(7) ? C18 C13 C11 . . 122.4(7) ? C14 C13 C11 . . 120.5(6) ? C15 C14 C13 . . 121.4(8) ? C15 C14 H14 . . 119.3 ? C13 C14 H14 . . 119.3 ? C14 C15 C16 . . 117.1(9) ? C14 C15 H15 . . 121.5 ? C16 C15 H15 . . 121.5 ? C17 C16 C15 . . 122.8(8) ? C17 C16 H16 . . 118.6 ? C15 C16 H16 . . 118.6 ? C16 C17 C18 . . 118.3(9) ? C16 C17 H17 . . 120.8 ? C18 C17 H17 . . 120.8 ? C13 C18 C17 . . 123.3(9) ? C13 C18 H18 . . 118.4 ? C17 C18 H18 . . 118.4 ? C28 C19 O4 . . 113.6(5) ? C28 C19 C20 . . 123.1(6) ? O4 C19 C20 . . 123.3(5) ? C21 C20 C19 . . 117.1(6) ? C21 C20 Br2 . . 123.7(5) ? C19 C20 Br2 . . 119.2(5) ? C20 C21 C22 . . 121.4(6) ? C20 C21 H21 . . 119.3 ? C22 C21 H21 . . 119.3 ? C27 C22 C23 . . 116.8(8) ? C27 C22 C21 . . 120.7(6) ? C23 C22 C21 . . 122.6(7) ? C24 C23 C22 . . 121.3(8) ? C24 C23 H23 . . 119.3 ? C22 C23 H23 . . 119.3 ? C23 C24 C25 . . 120.9(8) ? C23 C24 H24 . . 119.6 ? C25 C24 H24 . . 119.6 ? C26 C25 C24 . . 120.8(9) ? C26 C25 H25 . . 119.6 ? C24 C25 H25 . . 119.6 ? C25 C26 C27 . . 120.4(8) ? C25 C26 H26 . . 119.8 ? C27 C26 H26 . . 119.8 ? C22 C27 C26 . . 119.8(6) ? C22 C27 C28 . . 116.6(7) ? C26 C27 C28 . . 123.6(6) ? C19 C28 C27 . . 121.0(6) ? C19 C28 C29 . . 107.7(5) ? C27 C28 C29 . . 131.1(6) ? C31 C29 C28 . . 114.2(5) ? C31 C29 C30 . . 113.1(5) ? C28 C29 C30 . . 99.6(5) ? C31 C29 H29 . . 109.9 ? C28 C29 H29 . . 109.9 ? C30 C29 H29 . . 109.9 ? O4 C30 C29 . . 108.7(5) ? O4 C30 N2 . . 108.1(5) ? C29 C30 N2 . . 109.0(5) ? O4 C30 H30 . . 110.3 ? C29 C30 H30 . . 110.3 ? N2 C30 H30 . . 110.3 ? C32 C31 C36 . . 116.6(6) ? C32 C31 C29 . . 123.9(5) ? C36 C31 C29 . . 119.4(6) ? C31 C32 C33 . . 121.6(7) ? C31 C32 H32 . . 119.2 ? C33 C32 H32 . . 119.2 ? C34 C33 C32 . . 120.4(8) ? C34 C33 H33 . . 119.8 ? C32 C33 H33 . . 119.8 ? C33 C34 C35 . . 118.9(8) ? C33 C34 H34 . . 120.5 ? C35 C34 H34 . . 120.5 ? C36 C35 C34 . . 120.9(8) ? C36 C35 H35 . . 119.6 ? C34 C35 H35 . . 119.6 ? C35 C36 C31 . . 121.6(7) ? C35 C36 H36 . . 119.2 ? C31 C36 H36 . . 119.2 ? O3 N1 O2 . . 124.8(8) ? O3 N1 C12 . . 121.6(8) ? O2 N1 C12 . . 113.6(7) ? O5 N2 O6 . . 125.6(7) ? O5 N2 C30 . . 115.8(6) ? O6 N2 C30 . . 118.7(6) ? C12 O1 C1 . . 105.0(5) ? C30 O4 C19 . . 105.8(4) ? data_2 _database_code_depnum_ccdc_archive 'CCDC 902092' #TrackingRef 'compound-9j.cif' _chemical_name_systematic ? _chemical_name_common CJ143 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Br N O3' _chemical_formula_iupac ? _chemical_formula_weight 370.20 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.0050(11) _cell_length_b 12.3558(14) _cell_length_c 28.675(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3190.5(6) _cell_formula_units_Z 8 _cell_measurement_reflns_used 6137 _cell_measurement_theta_min 2.3706 _cell_measurement_theta_max 22.0990 _cell_measurement_temperature 296.(2) _exptl_crystal_description prismatic _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.180 _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 2.591 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.65 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 27019 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _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. ; _reflns_number_total 5842 _reflns_number_gt 4131 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_gt 0.1027 _refine_ls_wR_factor_ref 0.1279 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_number_reflns 5842 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refxyz _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+0.9214P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.412 _refine_diff_density_min -0.463 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(6) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(10) 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' _computing_data_collection 'Bruker Instrument Service v2010.9.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br Br1 0.65104(9) 1.01363(6) 1.085347(19) 0.0930(3) Uani d . 1 . . Br Br2 0.86253(9) 0.23061(6) 0.96825(2) 0.0888(3) Uani d . 1 . . C C1 0.7703(5) 0.8684(4) 0.86977(17) 0.0507(12) Uani d . 1 . . C C2 0.8580(6) 0.7787(4) 0.8772(2) 0.0622(13) Uani d . 1 . . H H2 0.8974 0.7397 0.8524 0.075 Uiso calc R 1 . . C C3 0.8852(5) 0.7490(4) 0.9224(2) 0.0649(15) Uani d . 1 . . H H3 0.9429 0.688 0.9282 0.078 Uiso calc R 1 . . C C4 0.8279(6) 0.8085(4) 0.96046(19) 0.0554(13) Uani d . 1 . . C C5 0.8563(6) 0.7798(5) 1.0070(2) 0.0710(16) Uani d . 1 . . H H5 0.9135 0.7188 1.0132 0.085 Uiso calc R 1 . . C C6 0.8028(6) 0.8385(5) 1.0431(2) 0.0701(16) Uani d . 1 . . H H6 0.8221 0.8179 1.0737 0.084 Uiso calc R 1 . . C C7 0.7184(6) 0.9302(4) 1.03380(18) 0.0573(13) Uani d . 1 . . C C8 0.6834(5) 0.9621(4) 0.98951(15) 0.0461(11) Uani d . 1 . . H H8 0.6251 1.0232 0.9846 0.055 Uiso calc R 1 . . C C9 0.7366(5) 0.9016(4) 0.95121(16) 0.0446(11) Uani d . 1 . . C C10 0.7093(5) 0.9287(4) 0.90417(15) 0.0410(11) Uani d . 1 . . C C11 0.6204(5) 1.0203(4) 0.88372(14) 0.0456(11) Uani d . 1 . . H H11 0.6666 1.0893 0.8922 0.055 Uiso calc R 1 . . C C12 0.6469(6) 0.9976(4) 0.83065(14) 0.0492(11) Uani d . 1 . . H H12 0.5519 0.9909 0.8142 0.059 Uiso calc R 1 . . C C13 0.4565(5) 1.0242(4) 0.89536(14) 0.0443(11) Uani d . 1 . . C C14 0.3737(6) 0.9317(4) 0.89984(16) 0.0533(12) Uani d . 1 . . H H14 0.4202 0.8649 0.897 0.064 Uiso calc R 1 . . C C15 0.2221(6) 0.9354(6) 0.9085(2) 0.0698(16) Uani d . 1 . . H H15 0.1678 0.872 0.9122 0.084 Uiso calc R 1 . . C C16 0.1543(7) 1.0342(7) 0.91152(19) 0.0806(18) Uani d . 1 . . H H16 0.0521 1.0381 0.9158 0.097 Uiso calc R 1 . . C C17 0.2347(8) 1.1262(6) 0.9083(2) 0.085(2) Uani d . 1 . . H H17 0.1874 1.1928 0.9112 0.102 Uiso calc R 1 . . C C18 0.3861(6) 1.1227(5) 0.9006(2) 0.0694(15) Uani d . 1 . . H H18 0.4405 1.1866 0.8991 0.083 Uiso calc R 1 . . C C19 0.7311(5) 0.5180(4) 0.78073(16) 0.0445(11) Uani d . 1 . . C C20 0.6400(5) 0.5997(4) 0.79980(19) 0.0555(12) Uani d . 1 . . H H20 0.5998 0.6542 0.7813 0.067 Uiso calc R 1 . . C C21 0.6141(5) 0.5950(4) 0.84603(19) 0.0563(13) Uani d . 1 . . H H21 0.5559 0.6485 0.8597 0.068 Uiso calc R 1 . . C C22 0.6723(5) 0.5114(4) 0.87479(17) 0.0528(12) Uani d . 1 . . C C23 0.6441(6) 0.5038(5) 0.92360(18) 0.0677(15) Uani d . 1 . . H H23 0.585 0.5565 0.9375 0.081 Uiso calc R 1 . . C C24 0.6988(7) 0.4238(5) 0.95064(19) 0.0735(17) Uani d . 1 . . H H24 0.6783 0.4218 0.9824 0.088 Uiso calc R 1 . . C C25 0.7884(5) 0.3429(5) 0.92954(17) 0.0576(13) Uani d . 1 . . C C26 0.8210(5) 0.3442(4) 0.88342(15) 0.0471(11) Uani d . 1 . . H H26 0.8796 0.2899 0.8706 0.057 Uiso calc R 1 . . C C27 0.7654(5) 0.4287(4) 0.85466(16) 0.0437(11) Uani d . 1 . . C C28 0.7940(4) 0.4371(3) 0.80637(16) 0.0397(10) Uani d . 1 . . C C29 0.8907(4) 0.3684(3) 0.77500(13) 0.0378(10) Uani d . 1 . . H H29 0.8595 0.2926 0.7772 0.045 Uiso calc R 1 . . C C30 0.8447(5) 0.4145(3) 0.72676(15) 0.0437(10) Uani d . 1 . . H H30 0.9325 0.4258 0.7071 0.052 Uiso calc R 1 . . C C31 1.0563(4) 0.3765(3) 0.78452(14) 0.0377(10) Uani d . 1 . . C C32 1.1241(5) 0.4779(4) 0.78915(14) 0.0449(10) Uani d . 1 . . H H32 1.0674 0.5406 0.7869 0.054 Uiso calc R 1 . . C C33 1.2762(5) 0.4851(5) 0.79714(15) 0.0533(12) Uani d . 1 . . H H33 1.3212 0.5525 0.7999 0.064 Uiso calc R 1 . . C C34 1.3597(6) 0.3929(4) 0.80089(15) 0.0537(12) Uani d . 1 . . H H34 1.4615 0.398 0.8059 0.064 Uiso calc R 1 . . C C35 1.2935(6) 0.2916(5) 0.79735(18) 0.0605(14) Uani d . 1 . . H H35 1.35 0.2291 0.8006 0.073 Uiso calc R 1 . . C C36 1.1411(5) 0.2848(4) 0.78881(16) 0.0494(11) Uani d . 1 . . H H36 1.0966 0.2172 0.786 0.059 Uiso calc R 1 . . N N1 0.7361(5) 1.0916(4) 0.81123(14) 0.0547(10) Uani d . 1 . . N N2 0.7393(5) 0.3343(3) 0.70392(13) 0.0498(10) Uani d . 1 . . O O1 0.7304(4) 0.9033(3) 0.82553(12) 0.0599(9) Uani d . 1 . . O O2 0.8689(4) 1.0908(3) 0.81499(14) 0.0748(11) Uani d . 1 . . O O3 0.6628(5) 1.1650(3) 0.79481(15) 0.0824(12) Uani d . 1 . . O O4 0.7695(4) 0.5128(2) 0.73387(10) 0.0517(8) Uani d . 1 . . O O5 0.8011(4) 0.2591(3) 0.68410(14) 0.0707(10) Uani d . 1 . . O O6 0.6068(4) 0.3459(3) 0.70801(13) 0.0648(10) Uani d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.1213(6) 0.1111(6) 0.0466(3) -0.0019(5) -0.0022(3) -0.0078(3) Br2 0.1165(6) 0.0940(5) 0.0559(3) 0.0158(5) 0.0102(4) 0.0177(3) C1 0.051(3) 0.043(3) 0.058(3) -0.012(2) 0.006(2) -0.005(2) C2 0.056(3) 0.050(3) 0.080(4) -0.012(3) 0.013(3) -0.018(3) C3 0.042(3) 0.046(3) 0.106(5) 0.002(2) 0.001(3) -0.005(3) C4 0.043(3) 0.048(3) 0.076(4) -0.004(2) -0.008(3) 0.003(3) C5 0.060(3) 0.066(4) 0.087(4) 0.008(3) -0.026(3) 0.016(3) C6 0.061(4) 0.083(4) 0.067(4) -0.009(3) -0.025(3) 0.019(3) C7 0.055(3) 0.068(3) 0.050(3) -0.005(3) -0.011(2) 0.004(3) C8 0.044(3) 0.051(3) 0.044(2) -0.004(2) -0.0058(19) -0.001(2) C9 0.033(2) 0.047(3) 0.054(3) -0.008(2) -0.0054(19) 0.002(2) C10 0.036(2) 0.040(3) 0.048(3) -0.009(2) 0.0031(19) -0.001(2) C11 0.052(3) 0.044(2) 0.041(2) -0.012(2) 0.002(2) 0.000(2) C12 0.054(3) 0.053(3) 0.041(2) -0.022(3) 0.001(2) 0.003(2) C13 0.051(3) 0.048(3) 0.034(2) -0.001(2) -0.0010(19) 0.006(2) C14 0.050(3) 0.046(3) 0.064(3) 0.001(3) 0.003(2) 0.000(2) C15 0.046(3) 0.087(5) 0.077(4) 0.000(3) 0.009(3) -0.009(3) C16 0.048(3) 0.127(6) 0.067(3) 0.011(4) 0.003(3) 0.003(4) C17 0.073(4) 0.089(5) 0.093(5) 0.039(4) 0.006(3) 0.006(4) C18 0.066(4) 0.063(4) 0.080(4) 0.009(3) 0.003(3) 0.007(3) C19 0.038(2) 0.036(2) 0.059(3) -0.011(2) -0.003(2) 0.001(2) C20 0.045(3) 0.044(3) 0.078(4) 0.006(2) -0.005(3) 0.001(2) C21 0.045(3) 0.046(3) 0.079(4) 0.000(2) 0.000(3) -0.013(3) C22 0.037(3) 0.059(3) 0.062(3) -0.002(2) 0.007(2) -0.017(3) C23 0.067(3) 0.073(4) 0.063(3) 0.011(3) 0.020(3) -0.016(3) C24 0.085(4) 0.090(4) 0.046(3) 0.001(3) 0.022(3) -0.010(3) C25 0.055(3) 0.069(3) 0.049(3) -0.002(3) 0.004(2) 0.003(3) C26 0.042(3) 0.052(3) 0.047(3) -0.002(2) 0.006(2) 0.002(2) C27 0.028(2) 0.053(3) 0.050(3) -0.009(2) 0.0030(19) -0.006(2) C28 0.028(2) 0.038(2) 0.053(3) -0.0064(19) 0.0026(18) -0.002(2) C29 0.032(2) 0.040(2) 0.042(2) -0.0015(18) 0.0031(17) 0.003(2) C30 0.040(2) 0.042(3) 0.049(2) -0.002(2) 0.000(2) 0.005(2) C31 0.035(2) 0.041(3) 0.037(2) 0.002(2) 0.0029(17) -0.002(2) C32 0.042(3) 0.045(3) 0.048(2) -0.004(2) 0.001(2) -0.001(2) C33 0.043(3) 0.063(3) 0.053(3) -0.012(3) 0.002(2) -0.007(3) C34 0.037(3) 0.073(4) 0.051(3) -0.007(3) -0.001(2) -0.006(2) C35 0.048(3) 0.071(4) 0.063(3) 0.018(3) -0.002(2) -0.001(3) C36 0.041(3) 0.044(3) 0.063(3) -0.003(2) 0.000(2) -0.004(2) N1 0.057(3) 0.059(3) 0.048(2) -0.018(2) 0.006(2) 0.004(2) N2 0.054(3) 0.051(3) 0.044(2) -0.001(2) -0.0099(18) 0.003(2) O1 0.075(2) 0.053(2) 0.051(2) -0.0129(19) 0.0110(17) -0.0109(17) O2 0.056(3) 0.079(3) 0.089(3) -0.021(2) 0.010(2) 0.003(2) O3 0.080(3) 0.075(3) 0.093(3) -0.010(3) 0.009(2) 0.032(2) O4 0.065(2) 0.0390(18) 0.0512(18) 0.0034(16) -0.0006(15) 0.0088(15) O5 0.070(3) 0.059(2) 0.083(3) 0.0080(19) -0.0040(19) -0.022(2) O6 0.040(2) 0.076(2) 0.079(2) -0.0030(18) -0.0115(17) -0.001(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C7 . 1.902(6) ? Br2 C25 . 1.898(5) ? C1 C10 . 1.352(6) ? C1 C2 . 1.378(7) ? C1 O1 . 1.387(6) ? C2 C3 . 1.368(7) ? C2 H2 . 0.93 ? C3 C4 . 1.414(7) ? C3 H3 . 0.93 ? C4 C5 . 1.404(7) ? C4 C9 . 1.438(7) ? C5 C6 . 1.353(8) ? C5 H5 . 0.93 ? C6 C7 . 1.389(8) ? C6 H6 . 0.93 ? C7 C8 . 1.367(7) ? C8 C9 . 1.413(6) ? C8 H8 . 0.93 ? C9 C10 . 1.412(6) ? C10 C11 . 1.505(6) ? C11 C13 . 1.514(6) ? C11 C12 . 1.566(6) ? C11 H11 . 0.98 ? C12 O1 . 1.395(6) ? C12 N1 . 1.518(6) ? C12 H12 . 0.98 ? C13 C14 . 1.370(7) ? C13 C18 . 1.381(7) ? C14 C15 . 1.388(7) ? C14 H14 . 0.93 ? C15 C16 . 1.368(9) ? C15 H15 . 0.93 ? C16 C17 . 1.351(9) ? C16 H16 . 0.93 ? C17 C18 . 1.382(9) ? C17 H17 . 0.93 ? C18 H18 . 0.93 ? C19 C28 . 1.364(6) ? C19 O4 . 1.389(5) ? C19 C20 . 1.411(7) ? C20 C21 . 1.347(7) ? C20 H20 . 0.93 ? C21 C22 . 1.422(7) ? C21 H21 . 0.93 ? C22 C23 . 1.426(7) ? C22 C27 . 1.442(6) ? C23 C24 . 1.349(8) ? C23 H23 . 0.93 ? C24 C25 . 1.421(8) ? C24 H24 . 0.93 ? C25 C26 . 1.355(7) ? C26 C27 . 1.421(7) ? C26 H26 . 0.93 ? C27 C28 . 1.412(6) ? C28 C29 . 1.513(6) ? C29 C31 . 1.519(6) ? C29 C30 . 1.552(6) ? C29 H29 . 0.98 ? C30 O4 . 1.406(5) ? C30 N2 . 1.521(6) ? C30 H30 . 0.98 ? C31 C36 . 1.372(6) ? C31 C32 . 1.400(6) ? C32 C33 . 1.392(7) ? C32 H32 . 0.93 ? C33 C34 . 1.369(7) ? C33 H33 . 0.93 ? C34 C35 . 1.390(7) ? C34 H34 . 0.93 ? C35 C36 . 1.396(7) ? C35 H35 . 0.93 ? C36 H36 . 0.93 ? N1 O2 . 1.201(5) ? N1 O3 . 1.217(6) ? N2 O6 . 1.208(5) ? N2 O5 . 1.222(5) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C10 C1 C2 . . 124.2(5) ? C10 C1 O1 . . 113.1(4) ? C2 C1 O1 . . 122.6(5) ? C3 C2 C1 . . 117.7(5) ? C3 C2 H2 . . 121.2 ? C1 C2 H2 . . 121.2 ? C2 C3 C4 . . 121.8(5) ? C2 C3 H3 . . 119.1 ? C4 C3 H3 . . 119.1 ? C5 C4 C3 . . 122.4(5) ? C5 C4 C9 . . 118.7(5) ? C3 C4 C9 . . 118.8(5) ? C6 C5 C4 . . 121.8(5) ? C6 C5 H5 . . 119.1 ? C4 C5 H5 . . 119.1 ? C5 C6 C7 . . 119.0(5) ? C5 C6 H6 . . 120.5 ? C7 C6 H6 . . 120.5 ? C8 C7 C6 . . 122.7(5) ? C8 C7 Br1 . . 119.4(4) ? C6 C7 Br1 . . 117.8(4) ? C7 C8 C9 . . 119.4(5) ? C7 C8 H8 . . 120.3 ? C9 C8 H8 . . 120.3 ? C10 C9 C8 . . 123.9(4) ? C10 C9 C4 . . 117.7(4) ? C8 C9 C4 . . 118.3(4) ? C1 C10 C9 . . 119.7(4) ? C1 C10 C11 . . 110.2(4) ? C9 C10 C11 . . 130.0(4) ? C10 C11 C13 . . 117.1(4) ? C10 C11 C12 . . 99.4(4) ? C13 C11 C12 . . 111.6(4) ? C10 C11 H11 . . 109.4 ? C13 C11 H11 . . 109.4 ? C12 C11 H11 . . 109.4 ? O1 C12 N1 . . 108.4(4) ? O1 C12 C11 . . 109.5(4) ? N1 C12 C11 . . 107.5(3) ? O1 C12 H12 . . 110.5 ? N1 C12 H12 . . 110.5 ? C11 C12 H12 . . 110.5 ? C14 C13 C18 . . 118.4(4) ? C14 C13 C11 . . 121.7(4) ? C18 C13 C11 . . 120.0(5) ? C13 C14 C15 . . 121.7(5) ? C13 C14 H14 . . 119.2 ? C15 C14 H14 . . 119.2 ? C16 C15 C14 . . 118.6(6) ? C16 C15 H15 . . 120.7 ? C14 C15 H15 . . 120.7 ? C17 C16 C15 . . 120.5(6) ? C17 C16 H16 . . 119.8 ? C15 C16 H16 . . 119.8 ? C16 C17 C18 . . 120.9(6) ? C16 C17 H17 . . 119.6 ? C18 C17 H17 . . 119.6 ? C13 C18 C17 . . 119.9(6) ? C13 C18 H18 . . 120.1 ? C17 C18 H18 . . 120.1 ? C28 C19 O4 . . 112.6(4) ? C28 C19 C20 . . 123.8(4) ? O4 C19 C20 . . 123.5(4) ? C21 C20 C19 . . 116.8(5) ? C21 C20 H20 . . 121.6 ? C19 C20 H20 . . 121.6 ? C20 C21 C22 . . 122.6(4) ? C20 C21 H21 . . 118.7 ? C22 C21 H21 . . 118.7 ? C21 C22 C23 . . 123.5(4) ? C21 C22 C27 . . 119.8(4) ? C23 C22 C27 . . 116.8(5) ? C24 C23 C22 . . 123.2(5) ? C24 C23 H23 . . 118.4 ? C22 C23 H23 . . 118.4 ? C23 C24 C25 . . 118.6(5) ? C23 C24 H24 . . 120.7 ? C25 C24 H24 . . 120.7 ? C26 C25 C24 . . 122.0(5) ? C26 C25 Br2 . . 120.2(4) ? C24 C25 Br2 . . 117.7(4) ? C25 C26 C27 . . 119.9(4) ? C25 C26 H26 . . 120.0 ? C27 C26 H26 . . 120.0 ? C28 C27 C26 . . 124.0(4) ? C28 C27 C22 . . 116.5(4) ? C26 C27 C22 . . 119.5(4) ? C19 C28 C27 . . 120.5(4) ? C19 C28 C29 . . 109.3(4) ? C27 C28 C29 . . 130.3(4) ? C28 C29 C31 . . 114.9(3) ? C28 C29 C30 . . 99.8(3) ? C31 C29 C30 . . 113.4(3) ? C28 C29 H29 . . 109.4 ? C31 C29 H29 . . 109.4 ? C30 C29 H29 . . 109.4 ? O4 C30 N2 . . 109.0(4) ? O4 C30 C29 . . 108.4(3) ? N2 C30 C29 . . 108.1(3) ? O4 C30 H30 . . 110.4 ? N2 C30 H30 . . 110.4 ? C29 C30 H30 . . 110.4 ? C36 C31 C32 . . 119.2(4) ? C36 C31 C29 . . 120.6(4) ? C32 C31 C29 . . 120.3(4) ? C33 C32 C31 . . 120.1(4) ? C33 C32 H32 . . 119.9 ? C31 C32 H32 . . 119.9 ? C34 C33 C32 . . 120.0(5) ? C34 C33 H33 . . 120.0 ? C32 C33 H33 . . 120.0 ? C33 C34 C35 . . 120.5(5) ? C33 C34 H34 . . 119.7 ? C35 C34 H34 . . 119.7 ? C34 C35 C36 . . 119.3(5) ? C34 C35 H35 . . 120.4 ? C36 C35 H35 . . 120.4 ? C31 C36 C35 . . 120.8(5) ? C31 C36 H36 . . 119.6 ? C35 C36 H36 . . 119.6 ? O2 N1 O3 . . 125.5(4) ? O2 N1 C12 . . 119.2(5) ? O3 N1 C12 . . 115.2(4) ? O6 N2 O5 . . 125.8(4) ? O6 N2 C30 . . 119.8(4) ? O5 N2 C30 . . 114.3(4) ? C1 O1 C12 . . 107.6(3) ? C19 O4 C30 . . 107.5(3) ?