# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ley, Steven' _publ_contact_author_email SVL1000@CAM.AC.UK loop_ _publ_author_name J.Shearman R.Myers J.Brenton S.Ley data_sl1040 _database_code_depnum_ccdc_archive 'CCDC 787666' #TrackingRef 'sl1040.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Br2 N O5' _chemical_formula_sum 'C11 H11 Br2 N O5' _chemical_formula_weight 397.03 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5189(1) _cell_length_b 10.7194(2) _cell_length_c 11.0482(2) _cell_angle_alpha 65.732(1) _cell_angle_beta 77.573(1) _cell_angle_gamma 80.693(1) _cell_volume 684.99(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7328 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.925 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 5.932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.447 _exptl_absorpt_correction_T_max 0.663 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12983 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 33.74 _reflns_number_total 5457 _reflns_number_gt 4133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0452P)^2^+0.2612P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5457 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.19287(4) 0.17792(3) 0.01444(2) 0.03365(7) Uani 1 1 d . . . Br2 Br -0.40696(4) 0.42347(2) -0.33741(3) 0.03230(7) Uani 1 1 d . . . N1 N 0.2148(3) 0.00166(18) -0.46388(17) 0.0215(3) Uani 1 1 d . . . O1 O -0.1326(3) 0.39899(18) -0.13432(17) 0.0304(3) Uani 1 1 d . . . O2 O -0.1892(3) 0.22037(18) -0.45349(17) 0.0295(3) Uani 1 1 d . . . H2 H -0.203(5) 0.160(3) -0.470(3) 0.035 Uiso 1 1 d . . . O3 O 0.1146(2) -0.01000(15) -0.33561(15) 0.0228(3) Uani 1 1 d . . . O4 O 0.4139(3) 0.07694(18) -0.72896(17) 0.0301(3) Uani 1 1 d . . . O5 O 0.4682(3) 0.27534(17) -0.72053(17) 0.0316(3) Uani 1 1 d . . . C1 C 0.0014(5) 0.5103(3) -0.1955(3) 0.0408(6) Uani 1 1 d . . . H1A H -0.0435 0.5754 -0.1515 0.061 Uiso 1 1 calc R . . H1B H -0.0084 0.5572 -0.2914 0.061 Uiso 1 1 calc R . . H1C H 0.1475 0.4743 -0.1853 0.061 Uiso 1 1 calc R . . C2 C -0.0774(3) 0.3009(2) -0.1879(2) 0.0244(4) Uani 1 1 d . . . C3 C 0.0904(3) 0.1926(2) -0.1390(2) 0.0235(4) Uani 1 1 d . . . C4 C 0.1709(3) 0.1052(2) -0.1982(2) 0.0244(4) Uani 1 1 d . . . H4 H 0.2717 0.0321 -0.1605 0.029 Uiso 1 1 calc R . . C5 C 0.0986(3) 0.1249(2) -0.3259(2) 0.0210(3) Uani 1 1 d . . . C6 C -0.1345(3) 0.1775(2) -0.3248(2) 0.0220(4) Uani 1 1 d . . . H6 H -0.2219 0.1011 -0.2602 0.026 Uiso 1 1 calc R . . C7 C -0.1808(3) 0.2952(2) -0.2779(2) 0.0222(4) Uani 1 1 d . . . C8 C 0.2446(3) 0.2106(2) -0.4525(2) 0.0246(4) Uani 1 1 d . . . H8A H 0.1743 0.3014 -0.5016 0.029 Uiso 1 1 calc R . . H8B H 0.3770 0.2235 -0.4305 0.029 Uiso 1 1 calc R . . C9 C 0.2828(3) 0.1211(2) -0.5302(2) 0.0211(3) Uani 1 1 d . . . C10 C 0.3941(3) 0.1526(2) -0.6702(2) 0.0231(4) Uani 1 1 d . . . C11 C 0.5862(5) 0.3182(3) -0.8564(3) 0.0381(6) Uani 1 1 d . . . H11A H 0.6147 0.4147 -0.8889 0.057 Uiso 1 1 calc R . . H11B H 0.5039 0.3077 -0.9156 0.057 Uiso 1 1 calc R . . H11C H 0.7199 0.2612 -0.8564 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.04591(15) 0.03698(14) 0.02420(11) -0.01397(9) -0.01399(9) -0.00362(10) Br2 0.02858(12) 0.02891(12) 0.04429(15) -0.01900(10) -0.01263(9) 0.00620(8) N1 0.0198(7) 0.0261(8) 0.0214(8) -0.0123(7) -0.0050(6) 0.0012(6) O1 0.0330(8) 0.0330(8) 0.0333(8) -0.0230(7) -0.0008(6) -0.0034(6) O2 0.0375(9) 0.0283(8) 0.0310(8) -0.0167(7) -0.0171(7) 0.0041(6) O3 0.0283(7) 0.0212(7) 0.0211(7) -0.0106(6) -0.0035(5) -0.0020(5) O4 0.0322(8) 0.0372(9) 0.0285(8) -0.0204(7) -0.0019(6) -0.0070(6) O5 0.0378(9) 0.0304(8) 0.0269(8) -0.0129(7) 0.0019(7) -0.0089(7) C1 0.0434(14) 0.0329(13) 0.0554(17) -0.0250(12) -0.0093(12) -0.0056(10) C2 0.0269(10) 0.0246(10) 0.0245(9) -0.0134(8) -0.0007(7) -0.0038(7) C3 0.0278(10) 0.0270(10) 0.0184(8) -0.0101(8) -0.0042(7) -0.0054(7) C4 0.0240(9) 0.0274(10) 0.0243(9) -0.0116(8) -0.0082(7) 0.0010(7) C5 0.0244(9) 0.0200(8) 0.0214(8) -0.0102(7) -0.0052(7) -0.0021(6) C6 0.0238(9) 0.0203(8) 0.0244(9) -0.0101(7) -0.0071(7) -0.0007(6) C7 0.0219(9) 0.0203(9) 0.0246(9) -0.0094(7) -0.0037(7) -0.0002(6) C8 0.0257(9) 0.0267(10) 0.0247(9) -0.0141(8) -0.0011(7) -0.0045(7) C9 0.0200(8) 0.0230(9) 0.0225(9) -0.0106(7) -0.0056(7) -0.0002(6) C10 0.0189(8) 0.0279(10) 0.0247(9) -0.0122(8) -0.0050(7) -0.0008(7) C11 0.0421(14) 0.0427(14) 0.0298(12) -0.0141(11) 0.0032(10) -0.0164(11) _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 C3 1.892(2) . ? Br2 C7 1.875(2) . ? N1 C9 1.283(3) . ? N1 O3 1.390(2) . ? O1 C2 1.372(2) . ? O1 C1 1.437(3) . ? O2 C6 1.410(2) . ? O2 H2 0.77(3) . ? O3 C5 1.479(2) . ? O4 C10 1.208(3) . ? O5 C10 1.327(3) . ? O5 C11 1.451(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.341(3) . ? C2 C3 1.472(3) . ? C3 C4 1.332(3) . ? C4 C5 1.506(3) . ? C4 H4 0.9500 . ? C5 C8 1.536(3) . ? C5 C6 1.532(3) . ? C6 C7 1.516(3) . ? C6 H6 1.0000 . ? C8 C9 1.493(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.482(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 O3 110.05(16) . . ? C2 O1 C1 113.36(18) . . ? C6 O2 H2 112(2) . . ? N1 O3 C5 109.26(15) . . ? C10 O5 C11 116.07(18) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 122.0(2) . . ? C7 C2 C3 118.41(18) . . ? O1 C2 C3 119.46(18) . . ? C4 C3 C2 122.58(19) . . ? C4 C3 Br1 119.41(16) . . ? C2 C3 Br1 118.01(14) . . ? C3 C4 C5 118.59(18) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? O3 C5 C4 108.84(16) . . ? O3 C5 C8 103.99(15) . . ? C4 C5 C8 112.35(17) . . ? O3 C5 C6 105.55(15) . . ? C4 C5 C6 111.78(16) . . ? C8 C5 C6 113.67(17) . . ? O2 C6 C7 110.01(16) . . ? O2 C6 C5 110.99(17) . . ? C7 C6 C5 110.03(16) . . ? O2 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? C2 C7 C6 121.50(18) . . ? C2 C7 Br2 120.97(15) . . ? C6 C7 Br2 117.25(14) . . ? C9 C8 C5 100.62(16) . . ? C9 C8 H8A 111.6 . . ? C5 C8 H8A 111.6 . . ? C9 C8 H8B 111.6 . . ? C5 C8 H8B 111.6 . . ? H8A C8 H8B 109.4 . . ? N1 C9 C10 117.75(18) . . ? N1 C9 C8 114.33(18) . . ? C10 C9 C8 127.88(18) . . ? O4 C10 O5 125.4(2) . . ? O4 C10 C9 124.5(2) . . ? O5 C10 C9 110.08(17) . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 O3 C5 6.8(2) . . . . ? C1 O1 C2 C7 -100.9(3) . . . . ? C1 O1 C2 C3 83.4(3) . . . . ? C7 C2 C3 C4 13.2(3) . . . . ? O1 C2 C3 C4 -171.0(2) . . . . ? C7 C2 C3 Br1 -166.53(16) . . . . ? O1 C2 C3 Br1 9.3(3) . . . . ? C2 C3 C4 C5 4.7(3) . . . . ? Br1 C3 C4 C5 -175.63(15) . . . . ? N1 O3 C5 C4 -132.27(16) . . . . ? N1 O3 C5 C8 -12.33(19) . . . . ? N1 O3 C5 C6 107.60(17) . . . . ? C3 C4 C5 O3 -151.45(19) . . . . ? C3 C4 C5 C8 93.9(2) . . . . ? C3 C4 C5 C6 -35.3(3) . . . . ? O3 C5 C6 O2 -73.17(19) . . . . ? C4 C5 C6 O2 168.66(16) . . . . ? C8 C5 C6 O2 40.2(2) . . . . ? O3 C5 C6 C7 164.83(16) . . . . ? C4 C5 C6 C7 46.7(2) . . . . ? C8 C5 C6 C7 -81.8(2) . . . . ? O1 C2 C7 C6 -173.15(19) . . . . ? C3 C2 C7 C6 2.6(3) . . . . ? O1 C2 C7 Br2 0.7(3) . . . . ? C3 C2 C7 Br2 176.42(15) . . . . ? O2 C6 C7 C2 -154.9(2) . . . . ? C5 C6 C7 C2 -32.3(3) . . . . ? O2 C6 C7 Br2 31.1(2) . . . . ? C5 C6 C7 Br2 153.65(14) . . . . ? O3 C5 C8 C9 12.34(19) . . . . ? C4 C5 C8 C9 129.88(17) . . . . ? C6 C5 C8 C9 -101.92(18) . . . . ? O3 N1 C9 C10 -179.82(16) . . . . ? O3 N1 C9 C8 2.2(2) . . . . ? C5 C8 C9 N1 -9.6(2) . . . . ? C5 C8 C9 C10 172.69(19) . . . . ? C11 O5 C10 O4 -1.5(3) . . . . ? C11 O5 C10 C9 178.4(2) . . . . ? N1 C9 C10 O4 4.8(3) . . . . ? C8 C9 C10 O4 -177.5(2) . . . . ? N1 C9 C10 O5 -175.14(18) . . . . ? C8 C9 C10 O5 2.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 33.74 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.590 _refine_diff_density_min -1.088 _refine_diff_density_rms 0.115 # Attachment 'CCDC-787667.cif' data_sl1041 _database_code_depnum_ccdc_archive 'CCDC 787667' #TrackingRef 'CCDC-787667.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Br2 N O5' _chemical_formula_sum 'C11 H11 Br2 N O5' _chemical_formula_weight 397.03 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9772(1) _cell_length_b 25.2605(3) _cell_length_c 10.1567(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.60(3) _cell_angle_gamma 90.00 _cell_volume 2725.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 32478 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 5.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.400 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 30388 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 30.97 _reflns_number_total 8610 _reflns_number_gt 5433 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0450P)^2^+0.7758P] 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_number_reflns 8610 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.004 _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 0.19330(3) 0.170561(14) 0.89744(4) 0.03343(10) Uani 1 1 d . . . Br2 Br -0.08877(4) 0.076956(15) 1.23493(4) 0.03944(11) Uani 1 1 d . . . O1 O 0.0705(3) 0.08092(10) 1.0315(3) 0.0482(7) Uani 1 1 d . . . N1 N -0.2451(3) 0.27451(11) 0.9219(3) 0.0294(6) Uani 1 1 d . . . C1 C 0.0112(4) 0.05967(17) 0.9000(5) 0.0550(12) Uani 1 1 d . . . H1A H 0.0650 0.0321 0.8765 0.082 Uiso 1 1 calc R . . H1B H -0.0013 0.0880 0.8320 0.082 Uiso 1 1 calc R . . H1C H -0.0704 0.0444 0.9016 0.082 Uiso 1 1 calc R . . C2 C 0.0359(3) 0.13117(13) 1.0551(3) 0.0310(7) Uani 1 1 d . . . O2 O 0.0450(2) 0.26875(9) 0.9488(2) 0.0350(6) Uani 1 1 d . . . H2 H 0.1176 0.2814 0.9599 0.053 Uiso 1 1 calc R . . C3 C -0.0495(3) 0.13811(14) 1.1455(3) 0.0306(7) Uani 1 1 d . . . O3 O -0.1811(2) 0.22659(9) 0.9524(2) 0.0284(5) Uani 1 1 d . . . C4 C -0.1005(3) 0.18430(14) 1.1644(3) 0.0296(7) Uani 1 1 d . . . H4 H -0.1492 0.1875 1.2292 0.036 Uiso 1 1 calc R . . O4 O -0.3575(3) 0.37293(11) 0.9229(3) 0.0499(7) Uani 1 1 d . . . O5 O -0.1805(3) 0.39568(10) 1.0780(3) 0.0459(7) Uani 1 1 d . . . C5 C -0.0804(3) 0.23140(13) 1.0823(3) 0.0255(7) Uani 1 1 d . . . C6 C 0.0463(3) 0.22950(13) 1.0480(3) 0.0281(7) Uani 1 1 d . . . H6 H 0.1122 0.2394 1.1317 0.034 Uiso 1 1 calc R . . C7 C 0.0772(3) 0.17467(13) 1.0056(3) 0.0301(7) Uani 1 1 d . . . C8 C -0.1054(3) 0.28594(13) 1.1357(3) 0.0293(7) Uani 1 1 d . . . H8A H -0.1362 0.2830 1.2190 0.035 Uiso 1 1 calc R . . H8B H -0.0288 0.3083 1.1550 0.035 Uiso 1 1 calc R . . C9 C -0.2046(3) 0.30720(13) 1.0195(3) 0.0271(7) Uani 1 1 d . . . C10 C -0.2592(4) 0.36164(15) 0.9996(4) 0.0336(8) Uani 1 1 d . . . C11 C -0.2191(5) 0.45075(17) 1.0565(5) 0.0633(14) Uani 1 1 d . . . H11A H -0.1536 0.4736 1.1118 0.095 Uiso 1 1 calc R . . H11B H -0.2980 0.4560 1.0832 0.095 Uiso 1 1 calc R . . H11C H -0.2316 0.4597 0.9602 0.095 Uiso 1 1 calc R . . Br1' Br -0.19229(4) 0.590783(15) 1.00126(4) 0.04145(11) Uani 1 1 d . . . Br2' Br -0.66919(4) 0.568098(15) 0.62390(4) 0.03796(10) Uani 1 1 d . . . O1' O -0.4028(2) 0.53664(9) 0.7820(2) 0.0348(6) Uani 1 1 d . . . N1' N -0.3802(3) 0.76937(10) 0.7470(2) 0.0250(6) Uani 1 1 d . . . C1' C -0.3601(4) 0.53131(17) 0.6602(4) 0.0496(10) Uani 1 1 d . . . H1'A H -0.3499 0.4937 0.6418 0.074 Uiso 1 1 calc R . . H1'B H -0.2792 0.5495 0.6721 0.074 Uiso 1 1 calc R . . H1'C H -0.4221 0.5471 0.5837 0.074 Uiso 1 1 calc R . . C2' C -0.4287(3) 0.58753(12) 0.8120(3) 0.0255(7) Uani 1 1 d . . . O2' O -0.2915(2) 0.70019(9) 1.0230(2) 0.0266(5) Uani 1 1 d . . . H2' H -0.3050 0.7116 1.0957 0.040 Uiso 1 1 calc R . . C3' C -0.5488(3) 0.61214(13) 0.7394(3) 0.0257(7) Uani 1 1 d . . . O3' O -0.3924(2) 0.71458(8) 0.7447(2) 0.0270(5) Uani 1 1 d . . . C4' C -0.5742(3) 0.66301(13) 0.7487(3) 0.0264(7) Uani 1 1 d . . . H4' H -0.6539 0.6769 0.7023 0.032 Uiso 1 1 calc R . . O4' O -0.5152(3) 0.86909(10) 0.9018(3) 0.0426(6) Uani 1 1 d . . . C5' C -0.4749(3) 0.69873(12) 0.8340(3) 0.0218(6) Uani 1 1 d . . . O5' O -0.3796(2) 0.87379(9) 0.7677(2) 0.0324(5) Uani 1 1 d . . . C6' C -0.3940(3) 0.66859(12) 0.9543(3) 0.0228(6) Uani 1 1 d . . . H6' H -0.4469 0.6610 1.0191 0.027 Uiso 1 1 calc R . . C7' C -0.3516(3) 0.61585(12) 0.9086(3) 0.0254(7) Uani 1 1 d . . . C8' C -0.5226(3) 0.75159(12) 0.8758(3) 0.0259(7) Uani 1 1 d . . . H8'A H -0.6141 0.7559 0.8359 0.031 Uiso 1 1 calc R . . H8'B H -0.5045 0.7550 0.9759 0.031 Uiso 1 1 calc R . . C9' C -0.4481(3) 0.79028(13) 0.8171(3) 0.0255(7) Uani 1 1 d . . . C10' C -0.4529(3) 0.84839(13) 0.8348(3) 0.0292(7) Uani 1 1 d . . . C11' C -0.3807(4) 0.93100(14) 0.7760(4) 0.0473(10) Uani 1 1 d . . . H11D H -0.3246 0.9458 0.7240 0.071 Uiso 1 1 calc R . . H11E H -0.3516 0.9419 0.8714 0.071 Uiso 1 1 calc R . . H11F H -0.4665 0.9440 0.7383 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02955(19) 0.0403(2) 0.03296(19) -0.00118(14) 0.01255(14) 0.00272(14) Br2 0.0437(2) 0.0368(2) 0.0366(2) 0.00722(15) 0.00800(16) -0.00817(16) O1 0.072(2) 0.0283(14) 0.0491(17) -0.0003(12) 0.0244(15) 0.0086(13) N1 0.0252(16) 0.0353(16) 0.0273(15) 0.0029(12) 0.0059(11) -0.0017(12) C1 0.042(3) 0.045(2) 0.081(3) -0.029(2) 0.021(2) -0.0065(19) C2 0.033(2) 0.0289(18) 0.0302(18) 0.0005(14) 0.0070(14) 0.0037(14) O2 0.0318(14) 0.0344(14) 0.0409(14) 0.0066(11) 0.0128(11) -0.0022(11) C3 0.032(2) 0.0286(18) 0.0304(18) 0.0010(14) 0.0056(14) -0.0060(14) O3 0.0264(13) 0.0337(13) 0.0224(11) -0.0049(9) 0.0011(9) -0.0025(10) C4 0.0337(19) 0.0374(19) 0.0192(16) -0.0010(13) 0.0093(13) -0.0021(15) O4 0.0362(17) 0.0512(18) 0.0579(18) 0.0144(14) 0.0039(13) 0.0129(13) O5 0.065(2) 0.0290(14) 0.0409(15) 0.0005(11) 0.0075(14) 0.0061(13) C5 0.0264(18) 0.0271(16) 0.0216(16) -0.0039(12) 0.0033(13) -0.0018(13) C6 0.0247(18) 0.0284(17) 0.0301(18) 0.0001(13) 0.0052(13) -0.0017(13) C7 0.0273(18) 0.0328(19) 0.0329(18) -0.0033(14) 0.0126(14) 0.0009(14) C8 0.0273(19) 0.0316(18) 0.0269(17) -0.0047(13) 0.0030(13) 0.0003(14) C9 0.0236(17) 0.0318(18) 0.0275(17) 0.0027(14) 0.0094(13) -0.0012(14) C10 0.035(2) 0.038(2) 0.0317(19) 0.0067(15) 0.0153(16) 0.0021(16) C11 0.098(4) 0.031(2) 0.058(3) 0.0023(19) 0.015(3) 0.015(2) Br1' 0.0330(2) 0.0346(2) 0.0486(2) 0.00013(16) -0.00487(16) 0.00914(15) Br2' 0.0341(2) 0.0387(2) 0.0375(2) -0.00881(15) 0.00243(15) -0.00836(15) O1' 0.0439(16) 0.0234(12) 0.0353(13) -0.0037(10) 0.0067(11) 0.0034(11) N1' 0.0323(16) 0.0198(13) 0.0236(14) 0.0005(10) 0.0085(11) 0.0011(11) C1' 0.050(3) 0.046(2) 0.058(3) -0.011(2) 0.022(2) 0.007(2) C2' 0.0309(19) 0.0204(16) 0.0259(17) 0.0023(12) 0.0084(13) 0.0009(13) O2' 0.0243(12) 0.0313(12) 0.0242(11) -0.0060(9) 0.0061(9) -0.0052(9) C3' 0.0246(17) 0.0291(17) 0.0236(16) -0.0009(13) 0.0063(13) -0.0033(13) O3' 0.0369(14) 0.0228(11) 0.0266(12) 0.0000(9) 0.0176(10) 0.0020(10) C4' 0.0267(18) 0.0305(17) 0.0208(16) 0.0002(13) 0.0039(13) 0.0006(13) O4' 0.0573(18) 0.0304(14) 0.0466(16) -0.0064(11) 0.0251(13) 0.0059(12) C5' 0.0253(17) 0.0212(15) 0.0209(15) -0.0004(12) 0.0097(12) 0.0007(12) O5' 0.0448(15) 0.0208(12) 0.0332(13) -0.0025(9) 0.0128(11) -0.0021(10) C6' 0.0255(17) 0.0254(16) 0.0184(15) -0.0016(12) 0.0074(12) -0.0016(13) C7' 0.0238(17) 0.0238(16) 0.0265(16) 0.0023(12) 0.0026(12) 0.0024(13) C8' 0.0277(18) 0.0265(17) 0.0263(17) -0.0005(13) 0.0119(13) 0.0034(13) C9' 0.0281(18) 0.0304(18) 0.0182(15) 0.0005(12) 0.0061(12) 0.0021(14) C10' 0.034(2) 0.0276(17) 0.0236(17) -0.0022(13) 0.0032(14) 0.0052(14) C11' 0.069(3) 0.0214(18) 0.055(3) 0.0006(17) 0.022(2) -0.0018(18) _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 C7 1.884(3) . ? Br2 C3 1.896(3) . ? O1 C2 1.363(4) . ? O1 C1 1.435(5) . ? N1 C9 1.280(4) . ? N1 O3 1.395(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C7 1.334(5) . ? C2 C3 1.478(5) . ? O2 C6 1.411(4) . ? O2 H2 0.8400 . ? C3 C4 1.329(5) . ? O3 C5 1.497(4) . ? C4 C5 1.501(5) . ? C4 H4 0.9500 . ? O4 C10 1.196(5) . ? O5 C10 1.332(5) . ? O5 C11 1.454(5) . ? C5 C6 1.517(5) . ? C5 C8 1.531(4) . ? C6 C7 1.514(5) . ? C6 H6 1.0000 . ? C8 C9 1.490(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.493(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? Br1' C7' 1.875(3) . ? Br2' C3' 1.892(3) . ? O1' C2' 1.367(4) . ? O1' C1' 1.435(4) . ? N1' C9' 1.269(4) . ? N1' O3' 1.390(3) . ? C1' H1'A 0.9800 . ? C1' H1'B 0.9800 . ? C1' H1'C 0.9800 . ? C2' C7' 1.331(4) . ? C2' C3' 1.476(5) . ? O2' C6' 1.412(4) . ? O2' H2' 0.8400 . ? C3' C4' 1.323(4) . ? O3' C5' 1.489(3) . ? C4' C5' 1.509(4) . ? C4' H4' 0.9500 . ? O4' C10' 1.199(4) . ? C5' C6' 1.522(4) . ? C5' C8' 1.533(4) . ? O5' C10' 1.341(4) . ? O5' C11' 1.448(4) . ? C6' C7' 1.522(4) . ? C6' H6' 1.0000 . ? C8' C9' 1.491(4) . ? C8' H8'A 0.9900 . ? C8' H8'B 0.9900 . ? C9' C10' 1.481(5) . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? 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 O1 C1 115.5(3) . . ? C9 N1 O3 109.3(3) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C2 O1 124.4(3) . . ? C7 C2 C3 117.7(3) . . ? O1 C2 C3 117.9(3) . . ? C6 O2 H2 109.5 . . ? C4 C3 C2 123.4(3) . . ? C4 C3 Br2 119.4(3) . . ? C2 C3 Br2 117.2(2) . . ? N1 O3 C5 110.1(2) . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C10 O5 C11 114.0(3) . . ? O3 C5 C4 104.2(2) . . ? O3 C5 C6 108.1(2) . . ? C4 C5 C6 112.0(3) . . ? O3 C5 C8 103.1(2) . . ? C4 C5 C8 116.9(3) . . ? C6 C5 C8 111.5(3) . . ? O2 C6 C7 113.8(3) . . ? O2 C6 C5 107.3(3) . . ? C7 C6 C5 112.2(3) . . ? O2 C6 H6 107.8 . . ? C7 C6 H6 107.8 . . ? C5 C6 H6 107.8 . . ? C2 C7 C6 121.7(3) . . ? C2 C7 Br1 121.2(3) . . ? C6 C7 Br1 116.7(2) . . ? C9 C8 C5 101.7(3) . . ? C9 C8 H8A 111.4 . . ? C5 C8 H8A 111.4 . . ? C9 C8 H8B 111.4 . . ? C5 C8 H8B 111.4 . . ? H8A C8 H8B 109.3 . . ? N1 C9 C8 115.0(3) . . ? N1 C9 C10 116.1(3) . . ? C8 C9 C10 128.8(3) . . ? O4 C10 O5 125.4(4) . . ? O4 C10 C9 125.0(4) . . ? O5 C10 C9 109.6(3) . . ? O5 C11 H11A 109.5 . . ? O5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2' O1' C1' 114.3(3) . . ? C9' N1' O3' 110.9(3) . . ? O1' C1' H1'A 109.5 . . ? O1' C1' H1'B 109.5 . . ? H1'A C1' H1'B 109.5 . . ? O1' C1' H1'C 109.5 . . ? H1'A C1' H1'C 109.5 . . ? H1'B C1' H1'C 109.5 . . ? C7' C2' O1' 122.7(3) . . ? C7' C2' C3' 117.6(3) . . ? O1' C2' C3' 119.6(3) . . ? C6' O2' H2' 109.5 . . ? C4' C3' C2' 123.4(3) . . ? C4' C3' Br2' 119.2(3) . . ? C2' C3' Br2' 117.3(2) . . ? N1' O3' C5' 109.2(2) . . ? C3' C4' C5' 119.2(3) . . ? C3' C4' H4' 120.4 . . ? C5' C4' H4' 120.4 . . ? O3' C5' C4' 105.9(2) . . ? O3' C5' C6' 107.6(2) . . ? C4' C5' C6' 110.7(3) . . ? O3' C5' C8' 103.7(2) . . ? C4' C5' C8' 115.6(3) . . ? C6' C5' C8' 112.6(2) . . ? C10' O5' C11' 115.7(3) . . ? O2' C6' C5' 110.2(2) . . ? O2' C6' C7' 112.3(3) . . ? C5' C6' C7' 110.7(2) . . ? O2' C6' H6' 107.8 . . ? C5' C6' H6' 107.8 . . ? C7' C6' H6' 107.8 . . ? C2' C7' C6' 120.6(3) . . ? C2' C7' Br1' 121.8(3) . . ? C6' C7' Br1' 117.4(2) . . ? C9' C8' C5' 101.6(2) . . ? C9' C8' H8'A 111.5 . . ? C5' C8' H8'A 111.5 . . ? C9' C8' H8'B 111.5 . . ? C5' C8' H8'B 111.5 . . ? H8'A C8' H8'B 109.3 . . ? N1' C9' C10' 121.6(3) . . ? N1' C9' C8' 114.2(3) . . ? C10' C9' C8' 124.1(3) . . ? O4' C10' O5' 125.5(3) . . ? O4' C10' C9' 122.9(3) . . ? O5' C10' C9' 111.6(3) . . ? O5' C11' H11D 109.5 . . ? O5' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? O5' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 C7 -76.9(5) . . . . ? C1 O1 C2 C3 105.4(4) . . . . ? C7 C2 C3 C4 9.7(5) . . . . ? O1 C2 C3 C4 -172.4(3) . . . . ? C7 C2 C3 Br2 -171.5(3) . . . . ? O1 C2 C3 Br2 6.3(4) . . . . ? C9 N1 O3 C5 -4.7(3) . . . . ? C2 C3 C4 C5 5.3(5) . . . . ? Br2 C3 C4 C5 -173.5(2) . . . . ? N1 O3 C5 C4 130.5(2) . . . . ? N1 O3 C5 C6 -110.3(3) . . . . ? N1 O3 C5 C8 7.9(3) . . . . ? C3 C4 C5 O3 84.9(4) . . . . ? C3 C4 C5 C6 -31.7(4) . . . . ? C3 C4 C5 C8 -162.0(3) . . . . ? O3 C5 C6 O2 53.8(3) . . . . ? C4 C5 C6 O2 168.0(3) . . . . ? C8 C5 C6 O2 -58.9(3) . . . . ? O3 C5 C6 C7 -71.9(3) . . . . ? C4 C5 C6 C7 42.4(4) . . . . ? C8 C5 C6 C7 175.4(3) . . . . ? O1 C2 C7 C6 -173.2(3) . . . . ? C3 C2 C7 C6 4.4(5) . . . . ? O1 C2 C7 Br1 -1.1(5) . . . . ? C3 C2 C7 Br1 176.6(2) . . . . ? O2 C6 C7 C2 -152.8(3) . . . . ? C5 C6 C7 C2 -30.8(5) . . . . ? O2 C6 C7 Br1 34.7(4) . . . . ? C5 C6 C7 Br1 156.7(2) . . . . ? O3 C5 C8 C9 -7.6(3) . . . . ? C4 C5 C8 C9 -121.3(3) . . . . ? C6 C5 C8 C9 108.2(3) . . . . ? O3 N1 C9 C8 -0.8(4) . . . . ? O3 N1 C9 C10 177.0(2) . . . . ? C5 C8 C9 N1 5.7(4) . . . . ? C5 C8 C9 C10 -171.9(3) . . . . ? C11 O5 C10 O4 -4.3(5) . . . . ? C11 O5 C10 C9 174.3(3) . . . . ? N1 C9 C10 O4 21.8(5) . . . . ? C8 C9 C10 O4 -160.7(4) . . . . ? N1 C9 C10 O5 -156.8(3) . . . . ? C8 C9 C10 O5 20.7(5) . . . . ? C1' O1' C2' C7' -103.4(4) . . . . ? C1' O1' C2' C3' 79.1(4) . . . . ? C7' C2' C3' C4' 11.8(5) . . . . ? O1' C2' C3' C4' -170.7(3) . . . . ? C7' C2' C3' Br2' -170.0(2) . . . . ? O1' C2' C3' Br2' 7.6(4) . . . . ? C9' N1' O3' C5' -3.9(3) . . . . ? C2' C3' C4' C5' 2.0(5) . . . . ? Br2' C3' C4' C5' -176.2(2) . . . . ? N1' O3' C5' C4' 128.7(2) . . . . ? N1' O3' C5' C6' -113.0(3) . . . . ? N1' O3' C5' C8' 6.5(3) . . . . ? C3' C4' C5' O3' 84.0(3) . . . . ? C3' C4' C5' C6' -32.3(4) . . . . ? C3' C4' C5' C8' -161.8(3) . . . . ? O3' C5' C6' O2' 57.0(3) . . . . ? C4' C5' C6' O2' 172.3(2) . . . . ? C8' C5' C6' O2' -56.6(3) . . . . ? O3' C5' C6' C7' -67.8(3) . . . . ? C4' C5' C6' C7' 47.5(3) . . . . ? C8' C5' C6' C7' 178.6(3) . . . . ? O1' C2' C7' C6' -169.7(3) . . . . ? C3' C2' C7' C6' 7.8(5) . . . . ? O1' C2' C7' Br1' 6.2(5) . . . . ? C3' C2' C7' Br1' -176.4(2) . . . . ? O2' C6' C7' C2' -161.2(3) . . . . ? C5' C6' C7' C2' -37.6(4) . . . . ? O2' C6' C7' Br1' 22.7(3) . . . . ? C5' C6' C7' Br1' 146.3(2) . . . . ? O3' C5' C8' C9' -6.4(3) . . . . ? C4' C5' C8' C9' -121.8(3) . . . . ? C6' C5' C8' C9' 109.6(3) . . . . ? O3' N1' C9' C10' -179.5(3) . . . . ? O3' N1' C9' C8' -0.7(4) . . . . ? C5' C8' C9' N1' 4.7(4) . . . . ? C5' C8' C9' C10' -176.5(3) . . . . ? C11' O5' C10' O4' -1.7(5) . . . . ? C11' O5' C10' C9' 178.4(3) . . . . ? N1' C9' C10' O4' -179.2(3) . . . . ? C8' C9' C10' O4' 2.2(5) . . . . ? N1' C9' C10' O5' 0.7(4) . . . . ? C8' C9' C10' O5' -178.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.97 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.988 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.117 # Attachment 'Compound-12.cif' data_sl1037 _database_code_depnum_ccdc_archive 'CCDC 795156' #TrackingRef 'Compound-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Br2 O4' _chemical_formula_sum 'C10 H6 Br2 O4' _chemical_formula_weight 349.97 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' 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 Pna2(1) _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 8.9710(2) _cell_length_b 10.6189(2) _cell_length_c 22.6185(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2154.69(8) _cell_formula_units_Z 8 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 10322 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 7.518 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.464 _exptl_absorpt_correction_T_max 0.734 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Entry XATGAB in CSD. Friedel pairs were averaged for the refinement. ; _diffrn_ambient_temperature 250(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 11137 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2504 _reflns_number_gt 2101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0696P)^2^+5.7543P] 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 mixed _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 0.15(3) _refine_ls_number_reflns 2504 _refine_ls_number_parameters 291 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.007 _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 0.79856(15) 0.01276(12) 0.59848(6) 0.0574(4) Uani 1 1 d . . . Br2 Br 0.36822(12) -0.07463(9) 0.41906(6) 0.0476(3) Uani 1 1 d . . . O1 O 0.3846(7) 0.2073(6) 0.4108(4) 0.0389(17) Uani 1 1 d . . . O2 O 0.2736(10) 0.3615(7) 0.3638(5) 0.056(2) Uani 1 1 d . . . O3 O 0.4334(10) 0.5438(6) 0.4213(5) 0.058(2) Uani 1 1 d . . . H3A H 0.3630 0.5511 0.3978 0.086 Uiso 1 1 calc R . . O4 O 0.5597(10) -0.1319(7) 0.5306(4) 0.054(2) Uani 1 1 d . . . C1 C 0.3658(11) 0.3323(9) 0.4006(5) 0.038(2) Uani 1 1 d . . . C2 C 0.4557(11) 0.4220(9) 0.4332(5) 0.039(2) Uani 1 1 d . . . C3 C 0.5511(11) 0.3815(9) 0.4747(5) 0.037(2) Uani 1 1 d . . . H3 H 0.6086 0.4399 0.4960 0.045 Uiso 1 1 calc R . . C4 C 0.6660(12) 0.2005(10) 0.5294(5) 0.040(2) Uani 1 1 d . . . H4 H 0.7318 0.2543 0.5496 0.048 Uiso 1 1 calc R . . C5 C 0.6653(13) 0.0717(11) 0.5412(5) 0.042(2) Uani 1 1 d . . . C6 C 0.5757(14) -0.0102(9) 0.5114(5) 0.041(2) Uani 1 1 d . . . C7 C 0.4853(12) 0.0351(10) 0.4655(5) 0.039(2) Uani 1 1 d . . . C8 C 0.4806(12) 0.1639(9) 0.4553(5) 0.037(2) Uani 1 1 d . . . C9 C 0.5655(12) 0.2496(9) 0.4865(5) 0.034(2) Uani 1 1 d . . . C10 C 0.6538(16) -0.2164(12) 0.5011(5) 0.058(3) Uani 1 1 d . . . H10A H 0.6257 -0.3021 0.5111 0.087 Uiso 1 1 calc R . . H10B H 0.7562 -0.2016 0.5131 0.087 Uiso 1 1 calc R . . H10C H 0.6448 -0.2041 0.4588 0.087 Uiso 1 1 calc R . . Br3 Br 0.30454(16) -0.00945(12) 0.61805(6) 0.0613(4) Uani 1 1 d . . . Br4 Br -0.14188(17) -0.09367(12) 0.79174(7) 0.0665(5) Uani 1 1 d . . . O5 O -0.1294(8) 0.1884(6) 0.7994(3) 0.0373(15) Uani 1 1 d . . . O6 O -0.2391(9) 0.3408(7) 0.8480(4) 0.0478(19) Uani 1 1 d . . . O7 O -0.0806(10) 0.5252(7) 0.7883(5) 0.057(2) Uani 1 1 d . . . H7A H -0.1284 0.5334 0.8195 0.086 Uiso 1 1 calc R . . O8 O 0.103(2) -0.1570(12) 0.7018(9) 0.158(9) Uani 1 1 d . . . C11 C -0.1493(13) 0.3131(10) 0.8116(5) 0.042(3) Uani 1 1 d . . . C12 C -0.0602(13) 0.4025(9) 0.7770(5) 0.042(3) Uani 1 1 d . . . C13 C 0.0395(13) 0.3634(10) 0.7370(6) 0.046(3) Uani 1 1 d . . . H13 H 0.0982 0.4226 0.7167 0.055 Uiso 1 1 calc R . . C14 C 0.1576(11) 0.1800(10) 0.6838(5) 0.040(2) Uani 1 1 d . . . H14 H 0.2183 0.2341 0.6613 0.047 Uiso 1 1 calc R . . C15 C 0.1672(12) 0.0532(11) 0.6762(6) 0.046(3) Uani 1 1 d . . . C16 C 0.0820(16) -0.0331(11) 0.7088(6) 0.057(3) Uani 1 1 d . . . C17 C -0.0210(13) 0.0171(10) 0.7481(6) 0.047(3) Uani 1 1 d . . . C18 C -0.0302(11) 0.1441(10) 0.7586(5) 0.036(2) Uani 1 1 d . . . C19 C 0.0575(12) 0.2300(10) 0.7249(5) 0.039(2) Uani 1 1 d . . . C20 C 0.057(4) -0.2394(18) 0.6822(15) 0.22(2) Uani 1 1 d . . . H20A H -0.0372 -0.2590 0.7008 0.327 Uiso 1 1 calc R . . H20B H 0.1257 -0.3093 0.6876 0.327 Uiso 1 1 calc R . . H20C H 0.0422 -0.2250 0.6403 0.327 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0627(8) 0.0608(7) 0.0489(7) 0.0118(6) -0.0111(6) 0.0155(5) Br2 0.0495(6) 0.0374(5) 0.0558(6) 0.0000(5) -0.0010(6) -0.0043(4) O1 0.036(4) 0.033(3) 0.048(5) 0.005(3) -0.008(3) 0.002(3) O2 0.060(5) 0.042(4) 0.066(6) 0.012(4) -0.023(4) 0.006(4) O3 0.063(5) 0.031(3) 0.078(6) 0.001(4) -0.013(5) 0.005(3) O4 0.064(5) 0.037(4) 0.062(5) 0.007(3) 0.008(4) 0.009(4) C1 0.033(5) 0.037(5) 0.045(6) 0.003(4) -0.010(4) -0.001(4) C2 0.038(5) 0.038(5) 0.042(6) 0.009(4) -0.001(5) 0.004(4) C3 0.031(5) 0.040(5) 0.041(6) 0.003(4) -0.005(4) 0.006(4) C4 0.037(5) 0.044(5) 0.038(6) 0.009(4) 0.001(5) -0.002(4) C5 0.047(6) 0.056(6) 0.023(5) 0.003(4) 0.002(5) 0.014(5) C6 0.051(6) 0.033(5) 0.038(5) 0.010(4) 0.003(5) 0.008(4) C7 0.038(5) 0.044(5) 0.035(5) 0.003(4) 0.004(5) 0.003(4) C8 0.039(5) 0.037(5) 0.035(6) 0.008(4) 0.002(4) -0.001(4) C9 0.030(5) 0.040(5) 0.032(5) 0.001(4) 0.008(4) -0.002(4) C10 0.079(9) 0.058(7) 0.037(6) 0.012(5) 0.008(6) 0.008(6) Br3 0.0617(8) 0.0611(7) 0.0610(9) -0.0154(6) 0.0215(7) 0.0056(5) Br4 0.0762(9) 0.0458(6) 0.0775(10) -0.0058(6) 0.0319(8) -0.0116(6) O5 0.040(4) 0.040(3) 0.031(4) -0.001(3) 0.006(3) 0.002(3) O6 0.047(4) 0.048(4) 0.048(5) -0.004(3) 0.013(4) 0.006(3) O7 0.061(5) 0.039(4) 0.071(6) -0.003(4) 0.024(5) 0.009(4) O8 0.214(18) 0.051(6) 0.210(19) -0.049(9) 0.146(16) -0.048(9) C11 0.046(6) 0.044(5) 0.037(6) 0.004(4) -0.011(5) 0.002(5) C12 0.043(6) 0.034(5) 0.048(7) -0.002(4) 0.000(5) 0.009(4) C13 0.050(6) 0.038(5) 0.050(6) 0.010(5) 0.001(5) 0.002(4) C14 0.033(5) 0.049(5) 0.037(6) 0.004(4) 0.006(5) -0.001(4) C15 0.042(6) 0.048(6) 0.049(7) -0.008(5) 0.013(6) 0.002(5) C16 0.066(8) 0.036(6) 0.070(9) -0.012(5) 0.022(7) -0.003(5) C17 0.037(6) 0.041(5) 0.062(8) -0.012(5) 0.003(6) -0.008(4) C18 0.030(5) 0.045(5) 0.033(5) -0.003(4) 0.001(4) 0.006(4) C19 0.038(6) 0.037(5) 0.044(6) -0.002(4) 0.005(5) 0.003(4) C20 0.27(4) 0.050(11) 0.33(5) 0.000(18) 0.22(4) 0.033(17) _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 C5 1.871(11) . ? Br2 C7 1.888(12) . ? O1 C1 1.359(12) . ? O1 C8 1.403(13) . ? O2 C1 1.213(14) . ? O3 C2 1.336(12) . ? O3 H3A 0.8300 . ? O4 C6 1.371(12) . ? O4 C10 1.401(15) . ? C1 C2 1.450(14) . ? C2 C3 1.340(15) . ? C3 C9 1.433(13) . ? C3 H3 0.9400 . ? C4 C5 1.394(15) . ? C4 C9 1.424(16) . ? C4 H4 0.9400 . ? C5 C6 1.362(17) . ? C6 C7 1.403(16) . ? C7 C8 1.387(15) . ? C8 C9 1.380(15) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? Br3 C15 1.921(11) . ? Br4 C17 1.881(13) . ? O5 C11 1.365(13) . ? O5 C18 1.365(12) . ? O6 C11 1.189(14) . ? O7 C12 1.340(12) . ? O7 H7A 0.8300 . ? O8 C20 1.06(3) . ? O8 C16 1.339(18) . ? C11 C12 1.467(16) . ? C12 C13 1.338(17) . ? C13 C19 1.452(14) . ? C13 H13 0.9400 . ? C14 C15 1.360(15) . ? C14 C19 1.398(15) . ? C14 H14 0.9400 . ? C15 C16 1.403(17) . ? C16 C17 1.387(17) . ? C17 C18 1.372(15) . ? C18 C19 1.425(15) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? 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 C1 O1 C8 121.3(8) . . ? C2 O3 H3A 109.5 . . ? C6 O4 C10 112.9(9) . . ? O2 C1 O1 116.8(9) . . ? O2 C1 C2 124.2(9) . . ? O1 C1 C2 119.1(9) . . ? O3 C2 C3 123.2(11) . . ? O3 C2 C1 116.7(10) . . ? C3 C2 C1 120.1(9) . . ? C2 C3 C9 120.1(10) . . ? C2 C3 H3 119.9 . . ? C9 C3 H3 119.9 . . ? C5 C4 C9 119.1(10) . . ? C5 C4 H4 120.5 . . ? C9 C4 H4 120.5 . . ? C6 C5 C4 122.4(10) . . ? C6 C5 Br1 120.4(8) . . ? C4 C5 Br1 117.2(9) . . ? C5 C6 O4 120.5(11) . . ? C5 C6 C7 119.2(9) . . ? O4 C6 C7 119.8(11) . . ? C8 C7 C6 118.6(10) . . ? C8 C7 Br2 119.9(8) . . ? C6 C7 Br2 121.4(8) . . ? C9 C8 C7 123.2(10) . . ? C9 C8 O1 119.3(9) . . ? C7 C8 O1 117.5(9) . . ? C8 C9 C4 117.2(9) . . ? C8 C9 C3 120.0(10) . . ? C4 C9 C3 122.8(10) . . ? O4 C10 H10A 109.5 . . ? O4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 O5 C18 123.9(8) . . ? C12 O7 H7A 109.5 . . ? C20 O8 C16 143(3) . . ? O6 C11 O5 118.0(10) . . ? O6 C11 C12 125.3(10) . . ? O5 C11 C12 116.6(10) . . ? C13 C12 O7 121.4(11) . . ? C13 C12 C11 121.6(10) . . ? O7 C12 C11 117.0(10) . . ? C12 C13 C19 120.3(10) . . ? C12 C13 H13 119.8 . . ? C19 C13 H13 119.8 . . ? C15 C14 C19 120.0(10) . . ? C15 C14 H14 120.0 . . ? C19 C14 H14 120.0 . . ? C14 C15 C16 123.1(10) . . ? C14 C15 Br3 118.0(8) . . ? C16 C15 Br3 118.9(8) . . ? O8 C16 C17 123.2(12) . . ? O8 C16 C15 120.2(12) . . ? C17 C16 C15 116.6(10) . . ? C18 C17 C16 121.9(11) . . ? C18 C17 Br4 119.3(9) . . ? C16 C17 Br4 118.7(8) . . ? O5 C18 C17 119.7(10) . . ? O5 C18 C19 120.0(9) . . ? C17 C18 C19 120.2(10) . . ? C14 C19 C18 117.9(9) . . ? C14 C19 C13 124.6(10) . . ? C18 C19 C13 117.5(10) . . ? O8 C20 H20A 109.5 . . ? O8 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O8 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O1 C1 O2 -175.5(10) . . . . ? C8 O1 C1 C2 4.9(15) . . . . ? O2 C1 C2 O3 0.1(18) . . . . ? O1 C1 C2 O3 179.7(10) . . . . ? O2 C1 C2 C3 177.5(12) . . . . ? O1 C1 C2 C3 -2.8(17) . . . . ? O3 C2 C3 C9 177.8(11) . . . . ? C1 C2 C3 C9 0.5(16) . . . . ? C9 C4 C5 C6 2.5(17) . . . . ? C9 C4 C5 Br1 -179.5(8) . . . . ? C4 C5 C6 O4 -169.0(10) . . . . ? Br1 C5 C6 O4 13.0(15) . . . . ? C4 C5 C6 C7 2.9(17) . . . . ? Br1 C5 C6 C7 -175.1(8) . . . . ? C10 O4 C6 C5 -96.6(13) . . . . ? C10 O4 C6 C7 91.6(13) . . . . ? C5 C6 C7 C8 -5.5(16) . . . . ? O4 C6 C7 C8 166.5(10) . . . . ? C5 C6 C7 Br2 175.8(9) . . . . ? O4 C6 C7 Br2 -12.2(14) . . . . ? C6 C7 C8 C9 2.8(16) . . . . ? Br2 C7 C8 C9 -178.5(8) . . . . ? C6 C7 C8 O1 -177.4(9) . . . . ? Br2 C7 C8 O1 1.3(13) . . . . ? C1 O1 C8 C9 -4.6(14) . . . . ? C1 O1 C8 C7 175.6(10) . . . . ? C7 C8 C9 C4 2.4(16) . . . . ? O1 C8 C9 C4 -177.4(10) . . . . ? C7 C8 C9 C3 -178.0(10) . . . . ? O1 C8 C9 C3 2.2(15) . . . . ? C5 C4 C9 C8 -5.1(16) . . . . ? C5 C4 C9 C3 175.4(10) . . . . ? C2 C3 C9 C8 -0.2(16) . . . . ? C2 C3 C9 C4 179.3(11) . . . . ? C18 O5 C11 O6 179.9(10) . . . . ? C18 O5 C11 C12 1.8(14) . . . . ? O6 C11 C12 C13 179.6(12) . . . . ? O5 C11 C12 C13 -2.4(16) . . . . ? O6 C11 C12 O7 1.2(18) . . . . ? O5 C11 C12 O7 179.1(10) . . . . ? O7 C12 C13 C19 -178.9(11) . . . . ? C11 C12 C13 C19 2.8(18) . . . . ? C19 C14 C15 C16 -1(2) . . . . ? C19 C14 C15 Br3 178.9(9) . . . . ? C20 O8 C16 C17 77(4) . . . . ? C20 O8 C16 C15 -104(3) . . . . ? C14 C15 C16 O8 -175.9(17) . . . . ? Br3 C15 C16 O8 4(2) . . . . ? C14 C15 C16 C17 3(2) . . . . ? Br3 C15 C16 C17 -176.8(11) . . . . ? O8 C16 C17 C18 173.5(17) . . . . ? C15 C16 C17 C18 -6(2) . . . . ? O8 C16 C17 Br4 -2(2) . . . . ? C15 C16 C17 Br4 178.6(10) . . . . ? C11 O5 C18 C17 -178.2(10) . . . . ? C11 O5 C18 C19 -1.5(15) . . . . ? C16 C17 C18 O5 -177.4(12) . . . . ? Br4 C17 C18 O5 -1.7(15) . . . . ? C16 C17 C18 C19 5.9(19) . . . . ? Br4 C17 C18 C19 -178.3(9) . . . . ? C15 C14 C19 C18 1.1(17) . . . . ? C15 C14 C19 C13 179.2(12) . . . . ? O5 C18 C19 C14 179.9(10) . . . . ? C17 C18 C19 C14 -3.5(16) . . . . ? O5 C18 C19 C13 1.7(15) . . . . ? C17 C18 C19 C13 178.3(11) . . . . ? C12 C13 C19 C14 179.6(12) . . . . ? C12 C13 C19 C18 -2.3(17) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.430 _refine_diff_density_min -0.968 _refine_diff_density_rms 0.126