# 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_global #TrackingRef '16685_web_deposit_cif_file_0_UweMonkowius_1357640698.tBoc_indigo.cif' _audit_update_record ; 2013-01-08 # Formatted by publCIF ; _audit_creation_method 'APEX2 v2010.1-2' data_I #TrackingRef '16685_web_deposit_cif_file_0_UweMonkowius_1357640698.tBoc_indigo.cif' _audit_creation_method 'APEX2 v2010.1-2' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C26 H26 N2 O6' _chemical_formula_sum 'C26 H26 N2 O6' _chemical_formula_iupac ? _chemical_formula_weight 462.49 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.069(9) _cell_length_b 7.368(3) _cell_length_c 17.190(7) _cell_angle_alpha 90 _cell_angle_beta 113.657(12) _cell_angle_gamma 90 _cell_volume 2444.3(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 300.(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour red _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ; _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 300.(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'sealed MicroFocus tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'SMART X2S' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10227 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.11 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _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 2162 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1136 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_number_reflns 2162 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.8866P] 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 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.175 _refine_diff_density_min -0.133 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0017(5) 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' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 O O1 0.07979(6) 0.93342(15) 0.21888(7) 0.0503(3) Uani d . 1 . . O O2 0.18484(7) 0.8000(2) 0.26878(11) 0.0902(6) Uani d . 1 . . O O3 -0.02689(6) 0.62147(17) 0.38619(8) 0.0604(4) Uani d . 1 . . N N1 0.09692(6) 0.68595(19) 0.29920(8) 0.0457(4) Uani d . 1 . . C C1 0.02401(12) 1.1638(3) 0.12524(16) 0.0888(8) Uani d . 1 . . H H11 -0.0086 1.0728 0.0932 0.133 Uiso calc R 1 . . H H1 0.026 1.258 0.0877 0.133 Uiso calc R 1 . . H H2 0.0097 1.2145 0.167 0.133 Uiso calc R 1 . . C C2 0.09448(9) 1.0792(3) 0.16876(12) 0.0583(5) Uani d . 1 . . C C3 0.12603(8) 0.8096(2) 0.26002(11) 0.0530(5) Uani d . 1 . . C C4 0.02713(8) 0.6855(2) 0.28813(10) 0.0422(4) Uani d . 1 . . C C5 0.14595(13) 1.2085(3) 0.22923(17) 0.1062(10) Uani d . 1 . . H H9 0.1305 1.2442 0.2724 0.159 Uiso calc R 1 . . H H10 0.15 1.314 0.1988 0.159 Uiso calc R 1 . . H H3 0.1902 1.15 0.2551 0.159 Uiso calc R 1 . . C C6 0.13742(8) 0.6102(2) 0.38081(11) 0.0470(4) Uani d . 1 . . C C7 0.20742(9) 0.5725(3) 0.41631(13) 0.0614(5) Uani d . 1 . . H H4 0.2357 0.5969 0.3877 0.074 Uiso calc R 1 . . C C8 0.23360(11) 0.4960(3) 0.49716(14) 0.0731(6) Uani d . 1 . . H H12 0.2805 0.4679 0.5228 0.088 Uiso calc R 1 . . C C9 0.19231(11) 0.4603(3) 0.54068(13) 0.0736(6) Uani d . 1 . . H H5 0.2119 0.4094 0.5947 0.088 Uiso calc R 1 . . C C10 0.12287(11) 0.4989(3) 0.50518(12) 0.0621(5) Uani d . 1 . . H H13 0.0948 0.4754 0.5342 0.075 Uiso calc R 1 . . C C11 0.09558(9) 0.5750(2) 0.42385(10) 0.0483(4) Uani d . 1 . . C C12 0.02472(9) 0.6299(2) 0.37084(11) 0.0456(4) Uani d . 1 . . C C13 0.11858(13) 0.9989(3) 0.10455(16) 0.0876(7) Uani d . 1 . . H H8 0.1636 0.9456 0.1335 0.131 Uiso calc R 1 . . H H6 0.1211 1.0926 0.0671 0.131 Uiso calc R 1 . . H H7 0.0864 0.9072 0.0722 0.131 Uiso calc R 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 O1 0.0508(7) 0.0469(7) 0.0566(7) 0.0007(5) 0.0252(6) 0.0099(5) O2 0.0498(8) 0.1121(13) 0.1169(13) 0.0147(8) 0.0421(8) 0.0558(11) O3 0.0665(8) 0.0642(8) 0.0648(8) 0.0068(6) 0.0412(7) 0.0115(7) N1 0.0430(7) 0.0504(8) 0.0462(7) 0.0030(6) 0.0203(6) 0.0075(6) C1 0.0900(16) 0.0750(15) 0.0976(17) 0.0138(12) 0.0337(14) 0.0351(14) C2 0.0653(11) 0.0507(10) 0.0578(11) -0.0091(8) 0.0234(9) 0.0122(9) C3 0.0440(10) 0.0597(11) 0.0578(10) 0.0019(8) 0.0231(8) 0.0114(9) C4 0.0458(8) 0.0380(8) 0.0465(8) 0.0013(6) 0.0225(7) 0.0014(7) C5 0.123(2) 0.0788(17) 0.0923(18) -0.0470(15) 0.0178(16) 0.0061(14) C6 0.0498(9) 0.0404(9) 0.0483(9) 0.0019(7) 0.0171(8) 0.0001(7) C7 0.0511(10) 0.0597(12) 0.0686(12) 0.0041(8) 0.0190(9) 0.0074(10) C8 0.0595(12) 0.0674(13) 0.0731(13) 0.0079(10) 0.0064(11) 0.0103(11) C9 0.0821(15) 0.0684(13) 0.0533(11) 0.0033(11) 0.0095(11) 0.0120(10) C10 0.0802(14) 0.0559(11) 0.0476(10) 0.0019(10) 0.0228(10) 0.0053(9) C11 0.0602(10) 0.0413(9) 0.0455(9) 0.0012(7) 0.0234(8) 0.0007(7) C12 0.0545(10) 0.0393(9) 0.0491(9) -0.0007(7) 0.0271(8) -0.0011(7) C13 0.1131(19) 0.0866(17) 0.0829(15) -0.0027(14) 0.0599(15) 0.0188(13) _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 O1 C3 . 1.315(2) ? O1 C2 . 1.485(2) ? O2 C3 . 1.189(2) ? O3 C12 . 1.219(2) ? N1 C4 . 1.405(2) ? N1 C3 . 1.411(2) ? N1 C6 . 1.431(2) ? C1 C2 . 1.504(3) ? C1 H11 . 0.96 ? C1 H1 . 0.96 ? C1 H2 . 0.96 ? C2 C5 . 1.503(3) ? C2 C13 . 1.509(3) ? C4 C4 2 1.350(3) ? C4 C12 . 1.500(2) ? C5 H9 . 0.96 ? C5 H10 . 0.96 ? C5 H3 . 0.96 ? C6 C7 . 1.379(2) ? C6 C11 . 1.384(2) ? C7 C8 . 1.392(3) ? C7 H4 . 0.93 ? C8 C9 . 1.381(3) ? C8 H12 . 0.93 ? C9 C10 . 1.370(3) ? C9 H5 . 0.93 ? C10 C11 . 1.398(2) ? C10 H13 . 0.93 ? C11 C12 . 1.460(2) ? C13 H8 . 0.96 ? C13 H6 . 0.96 ? C13 H7 . 0.96 ? 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 C3 O1 C2 . . 122.14(13) ? C4 N1 C3 . . 124.66(13) ? C4 N1 C6 . . 108.17(13) ? C3 N1 C6 . . 121.15(13) ? C2 C1 H11 . . 109.5 ? C2 C1 H1 . . 109.5 ? H11 C1 H1 . . 109.5 ? C2 C1 H2 . . 109.5 ? H11 C1 H2 . . 109.5 ? H1 C1 H2 . . 109.5 ? O1 C2 C5 . . 108.52(16) ? O1 C2 C1 . . 101.21(15) ? C5 C2 C1 . . 112.1(2) ? O1 C2 C13 . . 110.50(16) ? C5 C2 C13 . . 113.2(2) ? C1 C2 C13 . . 110.71(18) ? O2 C3 O1 . . 128.25(17) ? O2 C3 N1 . . 122.13(16) ? O1 C3 N1 . . 109.54(14) ? C4 C4 N1 2 . 124.32(19) ? C4 C4 C12 2 . 125.67(18) ? N1 C4 C12 . . 107.69(13) ? C2 C5 H9 . . 109.5 ? C2 C5 H10 . . 109.5 ? H9 C5 H10 . . 109.5 ? C2 C5 H3 . . 109.5 ? H9 C5 H3 . . 109.5 ? H10 C5 H3 . . 109.5 ? C7 C6 C11 . . 121.53(17) ? C7 C6 N1 . . 128.58(17) ? C11 C6 N1 . . 109.89(14) ? C6 C7 C8 . . 116.6(2) ? C6 C7 H4 . . 121.7 ? C8 C7 H4 . . 121.7 ? C9 C8 C7 . . 122.30(19) ? C9 C8 H12 . . 118.9 ? C7 C8 H12 . . 118.9 ? C10 C9 C8 . . 120.74(19) ? C10 C9 H5 . . 119.6 ? C8 C9 H5 . . 119.6 ? C9 C10 C11 . . 117.8(2) ? C9 C10 H13 . . 121.1 ? C11 C10 H13 . . 121.1 ? C6 C11 C10 . . 121.02(17) ? C6 C11 C12 . . 109.00(15) ? C10 C11 C12 . . 129.97(18) ? O3 C12 C11 . . 128.93(16) ? O3 C12 C4 . . 126.26(15) ? C11 C12 C4 . . 104.61(14) ? C2 C13 H8 . . 109.5 ? C2 C13 H6 . . 109.5 ? H8 C13 H6 . . 109.5 ? C2 C13 H7 . . 109.5 ? H8 C13 H7 . . 109.5 ? H6 C13 H7 . . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 O1 C2 C5 . . . . -70.0(2) ? C3 O1 C2 C1 . . . . 171.92(17) ? C3 O1 C2 C13 . . . . 54.6(2) ? C2 O1 C3 O2 . . . . 5.4(3) ? C2 O1 C3 N1 . . . . -177.97(14) ? C4 N1 C3 O2 . . . . -176.98(18) ? C6 N1 C3 O2 . . . . 33.6(3) ? C4 N1 C3 O1 . . . . 6.1(2) ? C6 N1 C3 O1 . . . . -143.30(15) ? C3 N1 C4 C4 . . . 2 51.46(19) ? C6 N1 C4 C4 . . . 2 -155.81(9) ? C3 N1 C4 C12 . . . . -145.05(16) ? C6 N1 C4 C12 . . . . 7.68(17) ? C4 N1 C6 C7 . . . . 175.15(17) ? C3 N1 C6 C7 . . . . -31.0(3) ? C4 N1 C6 C11 . . . . -4.52(19) ? C3 N1 C6 C11 . . . . 149.35(16) ? C11 C6 C7 C8 . . . . 0.5(3) ? N1 C6 C7 C8 . . . . -179.13(17) ? C6 C7 C8 C9 . . . . -0.5(3) ? C7 C8 C9 C10 . . . . 0.2(3) ? C8 C9 C10 C11 . . . . 0.1(3) ? C7 C6 C11 C10 . . . . -0.2(3) ? N1 C6 C11 C10 . . . . 179.48(15) ? C7 C6 C11 C12 . . . . 179.63(16) ? N1 C6 C11 C12 . . . . -0.68(19) ? C9 C10 C11 C6 . . . . -0.1(3) ? C9 C10 C11 C12 . . . . -179.90(18) ? C6 C11 C12 O3 . . . . -179.75(16) ? C10 C11 C12 O3 . . . . 0.1(3) ? C6 C11 C12 C4 . . . . 5.19(18) ? C10 C11 C12 C4 . . . . -174.99(17) ? C4 C4 C12 O3 2 . . . -19.9(2) ? N1 C4 C12 O3 . . . . 176.88(15) ? C4 C4 C12 C11 2 . . . 155.32(11) ? N1 C4 C12 C11 . . . . -7.89(17) ? _database_code_depnum_ccdc_archive 'CCDC 918485' ####################################################################### # # 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_global2 #TrackingRef '16686_web_deposit_cif_file_1_UweMonkowius_1357640698.tBoc_Br2indigo.cif' _audit_update_record ; 2013-01-08 # Formatted by publCIF ; _audit_creation_method 'APEX2 v2010.1-2' data_2 #TrackingRef '16686_web_deposit_cif_file_1_UweMonkowius_1357640698.tBoc_Br2indigo.cif' _audit_creation_method 'APEX2 v2010.1-2' _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C26 H24 Br2 N2 O6' _chemical_formula_sum 'C26 H24 Br2 N2 O6' _chemical_formula_iupac ? _chemical_formula_weight 620.29 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 2/c 1' _space_group_name_Hall '-P 2yc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.248(7) _cell_length_b 10.379(5) _cell_length_c 14.366(6) _cell_angle_alpha 90 _cell_angle_beta 111.215(11) _cell_angle_gamma 90 _cell_volume 2536.5(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 200.(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour red _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 3.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; ; _exptl_absorpt_correction_T_min 0.26 _exptl_absorpt_correction_T_max 0.42 _exptl_special_details ; ; _diffrn_ambient_temperature 200.(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'sealed MicroFocus tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'SMART X2S' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24402 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.18 _diffrn_reflns_theta_full 25.18 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _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 4535 _reflns_number_gt 3068 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_gt 0.1272 _refine_ls_wR_factor_ref 0.1412 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_number_reflns 4535 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+8.3674P] 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 1.284 _refine_diff_density_min -0.684 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 ? _computing_cell_refinement ? _computing_data_reduction ? _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 0.61204(4) 0.56526(9) 0.64251(5) 0.0468(2) Uani d . 1 . . Br Br2 -0.09713(4) -0.06995(8) 0.29526(5) 0.0388(2) Uani d . 1 . . O O1 0.1991(2) 0.4469(4) 0.6829(3) 0.0249(9) Uani d . 1 . . O O2 0.2982(2) 0.0771(4) 0.7411(3) 0.0254(9) Uani d . 1 . . O O3 0.2086(3) 0.6116(4) 0.5846(3) 0.0351(11) Uani d . 1 . . O O4 0.2902(3) -0.1060(4) 0.6521(3) 0.0392(12) Uani d . 1 . . O O5 0.1164(2) 0.3542(4) 0.4780(3) 0.0285(10) Uani d . 1 . . O O6 0.3949(2) 0.1476(4) 0.6286(3) 0.0287(10) Uani d . 1 . . N N1 0.2793(3) 0.4276(5) 0.5960(3) 0.0211(10) Uani d . 1 . . N N2 0.2284(3) 0.0776(4) 0.5761(3) 0.0203(10) Uani d . 1 . . C C1 0.1399(5) 0.4196(7) 0.8011(6) 0.055(2) Uani d . 1 . . H H1 0.1135 0.34 0.7698 0.083 Uiso calc R 1 . . H H8 0.111 0.4589 0.8395 0.083 Uiso calc R 1 . . H H7 0.1936 0.3998 0.8457 0.083 Uiso calc R 1 . . C C2 0.1423(4) 0.5119(6) 0.7214(5) 0.0307(15) Uani d . 1 . . C C3 0.2238(3) 0.5054(6) 0.6184(4) 0.0262(14) Uani d . 1 . . C C4 0.2848(3) 0.2932(6) 0.6028(4) 0.0200(13) Uani d . 1 . . C C5 0.2229(3) 0.2110(5) 0.5709(4) 0.0189(12) Uani d . 1 . . C C6 0.2770(3) 0.0051(6) 0.6604(4) 0.0225(13) Uani d . 1 . . C C7 0.3452(4) 0.0212(6) 0.8403(4) 0.0339(16) Uani d . 1 . . C C8 0.3014(4) -0.0891(7) 0.8633(5) 0.0450(19) Uani d . 1 . . H H18 0.2475 -0.0622 0.8528 0.067 Uiso calc R 1 . . H H19 0.3279 -0.1155 0.933 0.067 Uiso calc R 1 . . H H2 0.3002 -0.1617 0.8192 0.067 Uiso calc R 1 . . C C9 0.5061(3) 0.5272(7) 0.6255(4) 0.0306(16) Uani d . 1 . . C C10 0.4534(4) 0.6288(7) 0.6136(4) 0.0337(16) Uani d . 1 . . H H3 0.4713 0.7149 0.6143 0.04 Uiso calc R 1 . . C C11 0.3753(4) 0.6069(6) 0.6010(4) 0.0292(15) Uani d . 1 . . H H26 0.339 0.6757 0.5915 0.035 Uiso calc R 1 . . C C12 0.3526(3) 0.4773(6) 0.6030(4) 0.0229(14) Uani d . 1 . . C C13 0.1734(4) 0.6413(7) 0.7681(6) 0.0447(18) Uani d . 1 . . H H4 0.1362 0.6796 0.7951 0.067 Uiso calc R 1 . . H H6 0.1797 0.6985 0.7173 0.067 Uiso calc R 1 . . H H5 0.2244 0.6292 0.8221 0.067 Uiso calc R 1 . . C C14 0.0643(4) 0.5247(8) 0.6369(6) 0.051(2) Uani d . 1 . . H H9 0.0479 0.4404 0.6056 0.077 Uiso calc R 1 . . H H10 0.0694 0.5853 0.5872 0.077 Uiso calc R 1 . . H H11 0.0249 0.5569 0.6627 0.077 Uiso calc R 1 . . C C15 0.3511(5) 0.1340(8) 0.9097(5) 0.055(2) Uani d . 1 . . H H13 0.3805 0.2041 0.8936 0.083 Uiso calc R 1 . . H H12 0.3785 0.1067 0.9789 0.083 Uiso calc R 1 . . H H14 0.2982 0.1641 0.9014 0.083 Uiso calc R 1 . . C C16 0.4250(4) -0.0199(8) 0.8404(6) 0.050(2) Uani d . 1 . . H H16 0.4182 -0.0876 0.7905 0.076 Uiso calc R 1 . . H H15 0.457 -0.0528 0.9066 0.076 Uiso calc R 1 . . H H17 0.4514 0.0543 0.8242 0.076 Uiso calc R 1 . . C C17 0.1569(3) 0.0234(6) 0.5091(4) 0.0208(13) Uani d . 1 . . C C18 0.1342(4) -0.1035(6) 0.4907(4) 0.0258(14) Uani d . 1 . . H H22 0.1695 -0.1718 0.521 0.031 Uiso calc R 1 . . C C19 0.0590(4) -0.1277(6) 0.4271(4) 0.0273(14) Uani d . 1 . . H H21 0.0418 -0.2146 0.4139 0.033 Uiso calc R 1 . . C C20 0.0073(3) -0.0299(7) 0.3817(4) 0.0280(15) Uani d . 1 . . C C21 0.0283(3) 0.0976(6) 0.3975(4) 0.0243(14) Uani d . 1 . . H H20 -0.0072 0.1652 0.3663 0.029 Uiso calc R 1 . . C C22 0.1055(3) 0.1219(6) 0.4624(4) 0.0210(13) Uani d . 1 . . C C23 0.1421(3) 0.2463(6) 0.5018(4) 0.0194(13) Uani d . 1 . . C C24 0.3685(3) 0.2576(6) 0.6212(4) 0.0234(13) Uani d . 1 . . C C25 0.4067(3) 0.3794(6) 0.6173(4) 0.0212(13) Uani d . 1 . . C C26 0.4839(4) 0.4026(6) 0.6283(4) 0.0273(15) Uani d . 1 . . H H24 0.5203 0.3339 0.6374 0.033 Uiso calc R 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 0.0286(4) 0.0771(6) 0.0324(4) -0.0230(4) 0.0083(3) 0.0004(4) Br2 0.0296(4) 0.0563(5) 0.0298(4) -0.0182(3) 0.0097(3) -0.0128(3) O1 0.026(2) 0.022(2) 0.030(2) 0.0042(19) 0.0152(19) 0.0023(19) O2 0.030(2) 0.019(2) 0.024(2) -0.0002(19) 0.0059(18) 0.0008(18) O3 0.040(3) 0.017(3) 0.052(3) 0.007(2) 0.022(2) 0.007(2) O4 0.044(3) 0.020(3) 0.040(3) 0.009(2) 0.000(2) -0.002(2) O5 0.027(2) 0.022(3) 0.030(2) 0.0022(19) 0.0007(18) 0.0028(19) O6 0.026(2) 0.021(2) 0.039(3) 0.0034(19) 0.0106(19) -0.0006(19) N1 0.022(2) 0.014(3) 0.028(3) 0.001(2) 0.010(2) 0.001(2) N2 0.023(2) 0.015(3) 0.021(2) 0.000(2) 0.006(2) -0.002(2) C1 0.089(6) 0.035(4) 0.069(5) 0.004(4) 0.061(5) 0.003(4) C2 0.031(4) 0.022(4) 0.044(4) -0.004(3) 0.020(3) -0.016(3) C3 0.021(3) 0.025(4) 0.030(3) 0.001(3) 0.006(3) -0.006(3) C4 0.018(3) 0.023(3) 0.018(3) 0.003(3) 0.005(2) 0.004(2) C5 0.022(3) 0.016(3) 0.019(3) 0.002(2) 0.007(2) -0.001(2) C6 0.018(3) 0.022(4) 0.025(3) -0.004(3) 0.005(3) -0.004(3) C7 0.035(4) 0.032(4) 0.023(3) -0.008(3) -0.004(3) 0.006(3) C8 0.049(4) 0.042(5) 0.035(4) -0.006(4) 0.005(3) 0.016(3) C9 0.020(3) 0.049(5) 0.018(3) -0.011(3) 0.001(3) -0.004(3) C10 0.043(4) 0.033(4) 0.023(3) -0.021(3) 0.009(3) 0.002(3) C11 0.025(3) 0.028(4) 0.030(3) -0.006(3) 0.005(3) 0.001(3) C12 0.024(3) 0.032(4) 0.010(3) -0.005(3) 0.003(2) -0.001(2) C13 0.050(4) 0.031(4) 0.055(5) 0.000(4) 0.021(4) -0.013(4) C14 0.026(4) 0.066(6) 0.059(5) 0.006(4) 0.012(3) -0.009(4) C15 0.072(6) 0.056(5) 0.028(4) -0.006(4) 0.006(4) -0.010(4) C16 0.027(4) 0.060(5) 0.048(5) 0.003(4) -0.005(3) 0.013(4) C17 0.018(3) 0.027(3) 0.018(3) -0.005(3) 0.007(2) -0.003(2) C18 0.034(4) 0.018(3) 0.025(3) 0.000(3) 0.011(3) -0.002(2) C19 0.039(4) 0.025(3) 0.023(3) -0.013(3) 0.017(3) -0.009(3) C20 0.024(3) 0.042(4) 0.020(3) -0.013(3) 0.010(3) -0.010(3) C21 0.024(3) 0.031(4) 0.018(3) 0.001(3) 0.006(2) -0.001(3) C22 0.021(3) 0.020(3) 0.023(3) 0.000(3) 0.009(2) 0.002(2) C23 0.019(3) 0.020(3) 0.016(3) -0.002(3) 0.003(2) 0.002(2) C24 0.022(3) 0.029(4) 0.019(3) -0.005(3) 0.006(2) 0.000(3) C25 0.025(3) 0.023(3) 0.014(3) -0.001(3) 0.005(2) 0.002(2) C26 0.028(3) 0.032(4) 0.020(3) -0.001(3) 0.007(3) -0.002(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C9 . 1.900(6) ? Br2 C20 . 1.907(6) ? O1 C3 . 1.316(7) ? O1 C2 . 1.501(7) ? O2 C6 . 1.315(7) ? O2 C7 . 1.488(7) ? O3 C3 . 1.197(7) ? O4 C6 . 1.192(7) ? O5 C23 . 1.214(7) ? O6 C24 . 1.229(7) ? N1 C4 . 1.399(7) ? N1 C12 . 1.403(7) ? N1 C3 . 1.420(7) ? N2 C5 . 1.388(7) ? N2 C17 . 1.428(7) ? N2 C6 . 1.428(7) ? C1 C2 . 1.505(10) ? C1 H1 . 0.98 ? C1 H8 . 0.98 ? C1 H7 . 0.98 ? C2 C14 . 1.505(9) ? C2 C13 . 1.516(9) ? C4 C5 . 1.356(8) ? C4 C24 . 1.498(8) ? C5 C23 . 1.494(7) ? C7 C8 . 1.500(9) ? C7 C15 . 1.516(10) ? C7 C16 . 1.517(10) ? C8 H18 . 0.98 ? C8 H19 . 0.98 ? C8 H2 . 0.98 ? C9 C26 . 1.360(9) ? C9 C10 . 1.397(10) ? C10 C11 . 1.388(9) ? C10 H3 . 0.95 ? C11 C12 . 1.411(9) ? C11 H26 . 0.95 ? C12 C25 . 1.379(8) ? C13 H4 . 0.98 ? C13 H6 . 0.98 ? C13 H5 . 0.98 ? C14 H9 . 0.98 ? C14 H10 . 0.98 ? C14 H11 . 0.98 ? C15 H13 . 0.98 ? C15 H12 . 0.98 ? C15 H14 . 0.98 ? C16 H16 . 0.98 ? C16 H15 . 0.98 ? C16 H17 . 0.98 ? C17 C18 . 1.377(8) ? C17 C22 . 1.386(8) ? C18 C19 . 1.369(8) ? C18 H22 . 0.95 ? C19 C20 . 1.378(9) ? C19 H21 . 0.95 ? C20 C21 . 1.373(9) ? C21 C22 . 1.402(8) ? C21 H20 . 0.95 ? C22 C23 . 1.470(8) ? C24 C25 . 1.454(8) ? C25 C26 . 1.382(8) ? C26 H24 . 0.95 ? 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 C3 O1 C2 . . 120.7(5) ? C6 O2 C7 . . 120.4(5) ? C4 N1 C12 . . 108.6(5) ? C4 N1 C3 . . 126.2(5) ? C12 N1 C3 . . 120.9(5) ? C5 N2 C17 . . 109.0(5) ? C5 N2 C6 . . 125.6(5) ? C17 N2 C6 . . 120.0(5) ? C2 C1 H1 . . 109.5 ? C2 C1 H8 . . 109.5 ? H1 C1 H8 . . 109.5 ? C2 C1 H7 . . 109.5 ? H1 C1 H7 . . 109.5 ? H8 C1 H7 . . 109.5 ? O1 C2 C1 . . 102.0(5) ? O1 C2 C14 . . 108.6(5) ? C1 C2 C14 . . 113.0(6) ? O1 C2 C13 . . 111.3(5) ? C1 C2 C13 . . 109.7(6) ? C14 C2 C13 . . 111.8(6) ? O3 C3 O1 . . 128.5(6) ? O3 C3 N1 . . 120.8(6) ? O1 C3 N1 . . 110.6(5) ? C5 C4 N1 . . 124.9(5) ? C5 C4 C24 . . 125.2(5) ? N1 C4 C24 . . 107.5(5) ? C4 C5 N2 . . 125.0(5) ? C4 C5 C23 . . 124.9(5) ? N2 C5 C23 . . 108.4(5) ? O4 C6 O2 . . 129.2(6) ? O4 C6 N2 . . 120.7(5) ? O2 C6 N2 . . 110.0(5) ? O2 C7 C8 . . 109.9(5) ? O2 C7 C15 . . 102.0(5) ? C8 C7 C15 . . 111.2(6) ? O2 C7 C16 . . 109.4(5) ? C8 C7 C16 . . 111.9(6) ? C15 C7 C16 . . 112.1(6) ? C7 C8 H18 . . 109.5 ? C7 C8 H19 . . 109.5 ? H18 C8 H19 . . 109.5 ? C7 C8 H2 . . 109.5 ? H18 C8 H2 . . 109.5 ? H19 C8 H2 . . 109.5 ? C26 C9 C10 . . 121.5(6) ? C26 C9 Br1 . . 119.6(5) ? C10 C9 Br1 . . 118.9(5) ? C11 C10 C9 . . 121.5(6) ? C11 C10 H3 . . 119.3 ? C9 C10 H3 . . 119.3 ? C10 C11 C12 . . 116.6(6) ? C10 C11 H26 . . 121.7 ? C12 C11 H26 . . 121.7 ? C25 C12 N1 . . 110.6(5) ? C25 C12 C11 . . 120.4(5) ? N1 C12 C11 . . 128.9(6) ? C2 C13 H4 . . 109.5 ? C2 C13 H6 . . 109.5 ? H4 C13 H6 . . 109.5 ? C2 C13 H5 . . 109.5 ? H4 C13 H5 . . 109.5 ? H6 C13 H5 . . 109.5 ? C2 C14 H9 . . 109.5 ? C2 C14 H10 . . 109.5 ? H9 C14 H10 . . 109.5 ? C2 C14 H11 . . 109.5 ? H9 C14 H11 . . 109.5 ? H10 C14 H11 . . 109.5 ? C7 C15 H13 . . 109.5 ? C7 C15 H12 . . 109.5 ? H13 C15 H12 . . 109.5 ? C7 C15 H14 . . 109.5 ? H13 C15 H14 . . 109.5 ? H12 C15 H14 . . 109.5 ? C7 C16 H16 . . 109.5 ? C7 C16 H15 . . 109.5 ? H16 C16 H15 . . 109.5 ? C7 C16 H17 . . 109.5 ? H16 C16 H17 . . 109.5 ? H15 C16 H17 . . 109.5 ? C18 C17 C22 . . 120.6(5) ? C18 C17 N2 . . 130.2(5) ? C22 C17 N2 . . 109.2(5) ? C19 C18 C17 . . 117.6(6) ? C19 C18 H22 . . 121.2 ? C17 C18 H22 . . 121.2 ? C18 C19 C20 . . 121.9(6) ? C18 C19 H21 . . 119.0 ? C20 C19 H21 . . 119.0 ? C21 C20 C19 . . 122.0(5) ? C21 C20 Br2 . . 118.1(5) ? C19 C20 Br2 . . 119.9(5) ? C20 C21 C22 . . 115.8(6) ? C20 C21 H20 . . 122.1 ? C22 C21 H20 . . 122.1 ? C17 C22 C21 . . 122.0(5) ? C17 C22 C23 . . 109.2(5) ? C21 C22 C23 . . 128.4(5) ? O5 C23 C22 . . 128.8(5) ? O5 C23 C5 . . 126.9(5) ? C22 C23 C5 . . 104.0(5) ? O6 C24 C25 . . 129.2(5) ? O6 C24 C4 . . 126.0(5) ? C25 C24 C4 . . 104.5(5) ? C12 C25 C26 . . 122.3(6) ? C12 C25 C24 . . 108.6(5) ? C26 C25 C24 . . 129.1(6) ? C9 C26 C25 . . 117.7(6) ? C9 C26 H24 . . 121.2 ? C25 C26 H24 . . 121.2 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 O1 C2 C1 . . . . -172.6(6) ? C3 O1 C2 C14 . . . . 67.8(7) ? C3 O1 C2 C13 . . . . -55.7(7) ? C2 O1 C3 O3 . . . . 2.1(9) ? C2 O1 C3 N1 . . . . 177.7(4) ? C4 N1 C3 O3 . . . . -158.5(6) ? C12 N1 C3 O3 . . . . 47.5(8) ? C4 N1 C3 O1 . . . . 25.5(8) ? C12 N1 C3 O1 . . . . -128.4(5) ? C12 N1 C4 C5 . . . . -159.7(5) ? C3 N1 C4 C5 . . . . 43.6(8) ? C12 N1 C4 C24 . . . . 3.4(6) ? C3 N1 C4 C24 . . . . -153.2(5) ? N1 C4 C5 N2 . . . . 178.9(5) ? C24 C4 C5 N2 . . . . 18.6(9) ? N1 C4 C5 C23 . . . . 15.9(9) ? C24 C4 C5 C23 . . . . -144.3(5) ? C17 N2 C5 C4 . . . . -161.8(5) ? C6 N2 C5 C4 . . . . 44.5(8) ? C17 N2 C5 C23 . . . . 3.6(6) ? C6 N2 C5 C23 . . . . -150.1(5) ? C7 O2 C6 O4 . . . . -0.2(9) ? C7 O2 C6 N2 . . . . 176.3(4) ? C5 N2 C6 O4 . . . . -164.9(6) ? C17 N2 C6 O4 . . . . 44.0(8) ? C5 N2 C6 O2 . . . . 18.3(8) ? C17 N2 C6 O2 . . . . -132.8(5) ? C6 O2 C7 C8 . . . . -58.8(7) ? C6 O2 C7 C15 . . . . -176.8(5) ? C6 O2 C7 C16 . . . . 64.4(7) ? C26 C9 C10 C11 . . . . -2.1(9) ? Br1 C9 C10 C11 . . . . -179.9(4) ? C9 C10 C11 C12 . . . . 1.4(9) ? C4 N1 C12 C25 . . . . -1.8(6) ? C3 N1 C12 C25 . . . . 156.2(5) ? C4 N1 C12 C11 . . . . -179.2(6) ? C3 N1 C12 C11 . . . . -21.1(8) ? C10 C11 C12 C25 . . . . 0.2(8) ? C10 C11 C12 N1 . . . . 177.4(5) ? C5 N2 C17 C18 . . . . -177.9(6) ? C6 N2 C17 C18 . . . . -22.5(9) ? C5 N2 C17 C22 . . . . -0.9(6) ? C6 N2 C17 C22 . . . . 154.5(5) ? C22 C17 C18 C19 . . . . -1.6(8) ? N2 C17 C18 C19 . . . . 175.1(5) ? C17 C18 C19 C20 . . . . 0.7(9) ? C18 C19 C20 C21 . . . . 0.1(9) ? C18 C19 C20 Br2 . . . . -179.2(4) ? C19 C20 C21 C22 . . . . 0.1(8) ? Br2 C20 C21 C22 . . . . 179.4(4) ? C18 C17 C22 C21 . . . . 1.8(9) ? N2 C17 C22 C21 . . . . -175.5(5) ? C18 C17 C22 C23 . . . . 175.2(5) ? N2 C17 C22 C23 . . . . -2.1(6) ? C20 C21 C22 C17 . . . . -1.0(8) ? C20 C21 C22 C23 . . . . -173.0(5) ? C17 C22 C23 O5 . . . . 178.2(6) ? C21 C22 C23 O5 . . . . -9.0(10) ? C17 C22 C23 C5 . . . . 4.1(6) ? C21 C22 C23 C5 . . . . 176.9(6) ? C4 C5 C23 O5 . . . . -13.5(9) ? N2 C5 C23 O5 . . . . -178.9(5) ? C4 C5 C23 C22 . . . . 160.7(5) ? N2 C5 C23 C22 . . . . -4.7(6) ? C5 C4 C24 O6 . . . . -14.8(9) ? N1 C4 C24 O6 . . . . -177.9(5) ? C5 C4 C24 C25 . . . . 159.4(5) ? N1 C4 C24 C25 . . . . -3.6(6) ? N1 C12 C25 C26 . . . . -178.9(5) ? C11 C12 C25 C26 . . . . -1.3(8) ? N1 C12 C25 C24 . . . . -0.6(6) ? C11 C12 C25 C24 . . . . 177.0(5) ? O6 C24 C25 C12 . . . . 176.6(6) ? C4 C24 C25 C12 . . . . 2.6(6) ? O6 C24 C25 C26 . . . . -5.3(10) ? C4 C24 C25 C26 . . . . -179.3(5) ? C10 C9 C26 C25 . . . . 1.1(8) ? Br1 C9 C26 C25 . . . . 178.9(4) ? C12 C25 C26 C9 . . . . 0.6(8) ? C24 C25 C26 C9 . . . . -177.3(5) ? _database_code_depnum_ccdc_archive 'CCDC 918486'