data_su032 _publ_section_title SU032 _publ_contact_author_name 'Sushant Malhotra' _publ_contact_author_address 'Dept. of Chemistry, Stanford University' _publ_contact_author_email sushantm@stanford.edu _publ_contact_author_phone '+1 317 490 3615' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H25 Br O6' _chemical_formula_sum 'C24 H25 Br O6' _chemical_formula_weight 489.35 _chemical_absolute_configuration rmad 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 monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8101(6) _cell_length_b 13.0126(10) _cell_length_c 12.8280(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.991(2) _cell_angle_gamma 90.00 _cell_volume 1134.02(16) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2563 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 20.35 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 1.849 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6161 _exptl_absorpt_correction_T_max 0.7950 _exptl_absorpt_process_details 'SADABS, Sheldrick, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa X8-APEX-II' _diffrn_measurement_method 'combination of \w and \f-scans ' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 12969 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.44 _reflns_number_total 4446 _reflns_number_gt 3643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-II v2010-3' _computing_cell_refinement 'Bruker SAINT v7.68A' _computing_data_reduction 'Bruker SAINT v7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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. The vinyl side-chain was found to be disordered over two sites related by approximately 180 deg. rotation about the C-C bond to the core of the molecule. The site occupancies were refined and held to unity giving an approximate 0.6:0.4 ratio. This was left refined and not fixed. The disordered carbons were refined with isotropic thermal parameters. ; _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2232 Friedel pairs measured' _refine_ls_abs_structure_Flack 0.000(7) _refine_ls_number_reflns 4446 _refine_ls_number_parameters 282 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _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 0.68616(4) 0.39252(3) 1.46914(2) 0.02681(9) Uani 1 1 d . B . O1 O 0.1761(4) 0.4901(2) 0.6345(2) 0.0286(7) Uani 1 1 d . . . O2 O 0.2802(3) 0.54803(17) 0.79734(17) 0.0263(6) Uani 1 1 d . . . O3 O 0.1793(3) 0.46063(16) 0.99772(16) 0.0207(5) Uani 1 1 d . B . O4 O -0.0678(3) 0.3970(3) 1.08558(15) 0.0325(5) Uani 1 1 d . B . O5 O 0.5029(3) 0.3772(2) 0.79942(16) 0.0292(6) Uani 1 1 d . B . O6 O 0.2711(3) 0.28825(16) 0.87739(17) 0.0207(5) Uani 1 1 d . B . C1 C 0.1830(5) 0.4543(2) 0.8125(3) 0.0221(8) Uani 1 1 d . B . C2 C 0.0628(6) 0.4343(3) 0.7047(3) 0.0229(9) Uani 1 1 d . . . H2A H -0.0708 0.4659 0.7060 0.028 Uiso 1 1 calc R . . C3 C 0.2548(6) 0.5792(3) 0.6879(3) 0.0297(9) Uani 1 1 d . . . C4 C 0.0484(5) 0.4604(3) 0.9027(2) 0.0265(8) Uani 1 1 d . . . H4A H -0.0501 0.4033 0.9014 0.032 Uiso 1 1 calc R A 1 C5 C 0.1002(5) 0.4232(2) 1.0836(3) 0.0221(9) Uani 1 1 d . . . C6 C 0.2495(4) 0.4190(2) 1.1749(2) 0.0168(8) Uani 1 1 d . B . C7 C 0.4482(5) 0.4395(2) 1.1661(3) 0.0219(8) Uani 1 1 d . . . H7A H 0.4946 0.4576 1.1004 0.026 Uiso 1 1 calc R B . C8 C 0.5789(5) 0.4331(2) 1.2548(3) 0.0224(8) Uani 1 1 d . B . H8A H 0.7150 0.4471 1.2503 0.027 Uiso 1 1 calc R . . C9 C 0.5070(4) 0.4061(3) 1.3490(2) 0.0208(9) Uani 1 1 d . . . C10 C 0.3117(4) 0.3862(4) 1.3587(2) 0.0225(7) Uani 1 1 d . B . H10A H 0.2657 0.3684 1.4246 0.027 Uiso 1 1 calc R . . C11 C 0.1827(4) 0.3928(4) 1.2707(2) 0.0214(6) Uani 1 1 d . . . H11A H 0.0467 0.3791 1.2762 0.026 Uiso 1 1 calc R B . C12 C -0.0500(10) 0.5691(6) 0.9001(5) 0.0228(17) Uiso 0.598(10) 1 d P B 1 H12A H 0.0274 0.6290 0.9136 0.027 Uiso 0.598(10) 1 calc PR B 1 C13 C -0.2388(10) 0.5765(5) 0.8793(5) 0.034(2) Uiso 0.598(10) 1 d P B 1 H13A H -0.3153 0.5163 0.8659 0.041 Uiso 0.598(10) 1 calc PR B 1 H13B H -0.3003 0.6420 0.8775 0.041 Uiso 0.598(10) 1 calc PR B 1 C12A C -0.1131(15) 0.5352(8) 0.8981(7) 0.023(3) Uiso 0.402(10) 1 d P B 2 H12B H -0.2426 0.5152 0.8740 0.027 Uiso 0.402(10) 1 calc PR B 2 C13A C -0.0761(14) 0.6301(8) 0.9278(7) 0.034(3) Uiso 0.402(10) 1 d P B 2 H13C H 0.0538 0.6495 0.9518 0.041 Uiso 0.402(10) 1 calc PR B 2 H13D H -0.1791 0.6795 0.9253 0.041 Uiso 0.402(10) 1 calc PR B 2 C14 C 0.3402(5) 0.3701(3) 0.8295(2) 0.0216(9) Uani 1 1 d . . . C15 C 0.4008(5) 0.1989(2) 0.8847(3) 0.0261(9) Uani 1 1 d . . . H15A H 0.4580 0.1881 0.8167 0.031 Uiso 1 1 calc R B . H15B H 0.3229 0.1371 0.8999 0.031 Uiso 1 1 calc R . . C16 C 0.5660(5) 0.2118(3) 0.9694(3) 0.0358(10) Uani 1 1 d . B . H16A H 0.6353 0.1463 0.9805 0.054 Uiso 1 1 calc R . . H16B H 0.5109 0.2333 1.0345 0.054 Uiso 1 1 calc R . . H16C H 0.6583 0.2642 0.9478 0.054 Uiso 1 1 calc R . . C17 C 0.0434(6) 0.3248(3) 0.6702(3) 0.0225(9) Uani 1 1 d . . . C18 C 0.1926(6) 0.2752(3) 0.6205(3) 0.0231(10) Uani 1 1 d . . . H18A H 0.3093 0.3115 0.6074 0.028 Uiso 1 1 calc R . . C19 C 0.1718(5) 0.1737(3) 0.5902(3) 0.0273(9) Uani 1 1 d . . . H19A H 0.2738 0.1411 0.5555 0.033 Uiso 1 1 calc R . . C20 C 0.0040(6) 0.1192(3) 0.6097(3) 0.0298(9) Uani 1 1 d . . . H20A H -0.0102 0.0495 0.5883 0.036 Uiso 1 1 calc R . . C21 C -0.1434(5) 0.1673(3) 0.6609(3) 0.0298(9) Uani 1 1 d . . . H21A H -0.2578 0.1299 0.6760 0.036 Uiso 1 1 calc R . . C22 C -0.1254(5) 0.2696(3) 0.6903(3) 0.0262(8) Uani 1 1 d . . . H22A H -0.2283 0.3022 0.7242 0.031 Uiso 1 1 calc R . . C23 C 0.4533(6) 0.6030(3) 0.6484(3) 0.0374(10) Uani 1 1 d . . . H23A H 0.5403 0.5435 0.6599 0.056 Uiso 1 1 calc R . . H23B H 0.5109 0.6625 0.6862 0.056 Uiso 1 1 calc R . . H23C H 0.4378 0.6186 0.5736 0.056 Uiso 1 1 calc R . . C24 C 0.1120(6) 0.6692(3) 0.6784(3) 0.0361(10) Uani 1 1 d . . . H24A H -0.0175 0.6469 0.6985 0.054 Uiso 1 1 calc R . . H24B H 0.1009 0.6937 0.6060 0.054 Uiso 1 1 calc R . . H24C H 0.1608 0.7249 0.7247 0.054 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 0.03013(16) 0.02977(18) 0.01950(16) 0.0005(2) -0.00559(12) 0.0026(2) O1 0.051(2) 0.0192(16) 0.0160(15) 0.0033(12) 0.0058(13) 0.0072(13) O2 0.0383(15) 0.0216(14) 0.0190(14) 0.0035(11) 0.0008(11) 0.0059(11) O3 0.0236(12) 0.0285(13) 0.0096(12) 0.0015(10) -0.0004(10) 0.0009(10) O4 0.0224(11) 0.0544(15) 0.0206(11) 0.0004(18) 0.0006(9) -0.0096(19) O5 0.0284(12) 0.0279(18) 0.0328(13) 0.0067(14) 0.0126(10) 0.0072(13) O6 0.0213(12) 0.0222(13) 0.0188(13) 0.0051(11) 0.0020(10) 0.0067(10) C1 0.0279(19) 0.023(2) 0.0159(19) 0.0028(15) 0.0015(16) 0.0088(16) C2 0.028(2) 0.028(2) 0.014(2) 0.0027(15) 0.0050(17) 0.0099(16) C3 0.046(2) 0.025(2) 0.019(2) 0.0041(16) 0.0043(18) 0.0077(18) C4 0.0218(18) 0.044(2) 0.0129(19) -0.0008(16) -0.0009(15) 0.0137(16) C5 0.0265(18) 0.024(2) 0.0159(18) -0.0025(14) 0.0020(15) -0.0037(14) C6 0.0219(16) 0.014(2) 0.0140(17) -0.0008(12) 0.0000(13) 0.0012(12) C7 0.0229(18) 0.0261(19) 0.0171(19) 0.0006(15) 0.0043(15) -0.0024(14) C8 0.0177(16) 0.026(2) 0.024(2) 0.0020(14) 0.0025(15) -0.0012(13) C9 0.0250(16) 0.019(2) 0.0177(16) -0.0008(18) -0.0028(13) 0.0019(18) C10 0.0270(15) 0.0259(18) 0.0152(15) 0.004(2) 0.0049(12) 0.002(2) C11 0.0205(14) 0.0223(16) 0.0217(16) 0.007(2) 0.0036(12) 0.004(2) C14 0.0294(18) 0.021(3) 0.0152(17) 0.0024(15) 0.0040(15) 0.0057(16) C15 0.032(2) 0.017(2) 0.030(2) 0.0044(16) 0.0015(17) 0.0101(15) C16 0.026(2) 0.030(2) 0.051(3) 0.0115(19) -0.0050(19) 0.0034(17) C17 0.031(2) 0.028(2) 0.009(2) 0.0050(16) 0.0007(17) 0.0115(18) C18 0.027(2) 0.024(2) 0.019(2) 0.0026(18) 0.0035(17) 0.0034(17) C19 0.032(2) 0.031(2) 0.020(2) 0.0018(17) 0.0109(17) 0.0088(17) C20 0.042(2) 0.024(2) 0.024(2) 0.0011(17) 0.0028(18) 0.0049(18) C21 0.029(2) 0.034(2) 0.026(2) 0.0039(18) 0.0039(17) 0.0038(17) C22 0.0260(19) 0.035(2) 0.018(2) 0.0026(17) 0.0029(16) 0.0122(17) C23 0.053(3) 0.027(2) 0.034(2) 0.0088(18) 0.014(2) 0.0082(19) C24 0.053(3) 0.025(2) 0.030(2) 0.0064(18) 0.000(2) 0.0119(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C9 1.906(3) . ? O1 C2 1.425(4) . ? O1 C3 1.432(4) . ? O2 C1 1.408(4) . ? O2 C3 1.460(4) . ? O3 C5 1.350(4) . ? O3 C4 1.459(3) . ? O4 C5 1.196(4) . ? O5 C14 1.202(4) . ? O6 C14 1.332(4) . ? O6 C15 1.459(4) . ? C1 C4 1.527(4) . ? C1 C14 1.536(4) . ? C1 C2 1.578(5) . ? C2 C17 1.495(5) . ? C3 C23 1.508(5) . ? C3 C24 1.521(5) . ? C4 C12A 1.467(11) . ? C4 C12 1.565(8) . ? C5 C6 1.498(4) . ? C6 C11 1.383(4) . ? C6 C7 1.391(4) . ? C7 C8 1.398(4) . ? C8 C9 1.380(4) . ? C9 C10 1.370(4) . ? C10 C11 1.384(3) . ? C12 C13 1.298(10) . ? C12A C13A 1.312(15) . ? C15 C16 1.517(4) . ? C17 C22 1.394(5) . ? C17 C18 1.395(5) . ? C18 C19 1.381(5) . ? C19 C20 1.383(5) . ? C20 C21 1.387(5) . ? C21 C22 1.387(5) . ? C2 H2A 1.0000 . ? C4 H4A 1.0000 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C13 H13B 0.9500 . ? C12A H12B 0.9500 . ? C13A H13C 0.9500 . ? C13A H13D 0.9500 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C3 108.1(3) . . ? C1 O2 C3 110.4(2) . . ? C5 O3 C4 115.2(2) . . ? C14 O6 C15 115.8(3) . . ? O2 C1 C4 111.8(3) . . ? O2 C1 C14 107.9(3) . . ? C4 C1 C14 112.3(3) . . ? O2 C1 C2 104.0(3) . . ? C4 C1 C2 111.8(3) . . ? C14 C1 C2 108.7(3) . . ? O1 C2 C17 109.9(3) . . ? O1 C2 C1 101.5(3) . . ? C17 C2 C1 116.5(3) . . ? O1 C3 O2 104.5(3) . . ? O1 C3 C23 108.7(3) . . ? O2 C3 C23 109.3(3) . . ? O1 C3 C24 111.7(3) . . ? O2 C3 C24 108.8(3) . . ? C23 C3 C24 113.4(3) . . ? O3 C4 C12A 116.4(4) . . ? O3 C4 C1 105.6(3) . . ? C12A C4 C1 119.5(4) . . ? O3 C4 C12 104.6(3) . . ? C12A C4 C12 23.1(4) . . ? C1 C4 C12 108.0(3) . . ? O4 C5 O3 123.9(3) . . ? O4 C5 C6 124.8(3) . . ? O3 C5 C6 111.3(3) . . ? C11 C6 C7 120.1(3) . . ? C11 C6 C5 117.1(3) . . ? C7 C6 C5 122.7(3) . . ? C6 C7 C8 119.4(3) . . ? C9 C8 C7 118.9(3) . . ? C10 C9 C8 122.3(3) . . ? C10 C9 Br1 118.7(2) . . ? C8 C9 Br1 119.0(2) . . ? C9 C10 C11 118.7(3) . . ? C6 C11 C10 120.7(3) . . ? C13 C12 C4 119.1(7) . . ? C13A C12A C4 119.0(9) . . ? O5 C14 O6 124.9(3) . . ? O5 C14 C1 123.3(3) . . ? O6 C14 C1 111.7(3) . . ? O6 C15 C16 111.9(3) . . ? C22 C17 C18 118.9(4) . . ? C22 C17 C2 119.5(3) . . ? C18 C17 C2 121.6(4) . . ? C19 C18 C17 120.5(4) . . ? C18 C19 C20 120.6(3) . . ? C19 C20 C21 119.3(3) . . ? C22 C21 C20 120.6(3) . . ? C21 C22 C17 120.2(3) . . ? O1 C2 H2A 109.5 . . ? C17 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? O3 C4 H4A 112.7 . . ? C12A C4 H4A 89.5 . . ? C1 C4 H4A 112.7 . . ? C12 C4 H4A 112.7 . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C9 C10 H10A 120.7 . . ? C11 C10 H10A 120.7 . . ? C6 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C13 C12 H12A 120.4 . . ? C4 C12 H12A 120.4 . . ? C12 C13 H13A 120.0 . . ? C12 C13 H13B 120.0 . . ? H13A C13 H13B 120.0 . . ? C13A C12A H12B 120.5 . . ? C4 C12A H12B 120.5 . . ? C12A C13A H13C 120.0 . . ? C12A C13A H13D 120.0 . . ? H13C C13A H13D 120.0 . . ? O6 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? O6 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C19 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? C18 C19 H19A 119.7 . . ? C20 C19 H19A 119.7 . . ? C19 C20 H20A 120.4 . . ? C21 C20 H20A 120.4 . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C21 C22 H22A 119.9 . . ? C17 C22 H22A 119.9 . . ? C3 C23 H23A 109.5 . . ? C3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C3 C24 H24A 109.5 . . ? C3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C3 O2 C1 C4 -129.0(3) . . . . ? C3 O2 C1 C14 107.1(3) . . . . ? C3 O2 C1 C2 -8.2(3) . . . . ? C3 O1 C2 C17 -158.2(3) . . . . ? C3 O1 C2 C1 -34.4(3) . . . . ? O2 C1 C2 O1 25.6(3) . . . . ? C4 C1 C2 O1 146.4(3) . . . . ? C14 C1 C2 O1 -89.2(3) . . . . ? O2 C1 C2 C17 144.9(3) . . . . ? C4 C1 C2 C17 -94.4(4) . . . . ? C14 C1 C2 C17 30.1(5) . . . . ? C2 O1 C3 O2 30.3(4) . . . . ? C2 O1 C3 C23 146.9(3) . . . . ? C2 O1 C3 C24 -87.2(3) . . . . ? C1 O2 C3 O1 -12.3(3) . . . . ? C1 O2 C3 C23 -128.4(3) . . . . ? C1 O2 C3 C24 107.1(3) . . . . ? C5 O3 C4 C12A 71.4(6) . . . . ? C5 O3 C4 C1 -153.4(3) . . . . ? C5 O3 C4 C12 92.7(4) . . . . ? O2 C1 C4 O3 -73.6(3) . . . . ? C14 C1 C4 O3 47.8(4) . . . . ? C2 C1 C4 O3 170.3(3) . . . . ? O2 C1 C4 C12A 59.9(6) . . . . ? C14 C1 C4 C12A -178.6(5) . . . . ? C2 C1 C4 C12A -56.2(6) . . . . ? O2 C1 C4 C12 37.9(4) . . . . ? C14 C1 C4 C12 159.3(4) . . . . ? C2 C1 C4 C12 -78.3(4) . . . . ? C4 O3 C5 O4 -4.3(5) . . . . ? C4 O3 C5 C6 175.6(2) . . . . ? O4 C5 C6 C11 -6.9(5) . . . . ? O3 C5 C6 C11 173.1(3) . . . . ? O4 C5 C6 C7 172.6(4) . . . . ? O3 C5 C6 C7 -7.3(4) . . . . ? C11 C6 C7 C8 0.1(5) . . . . ? C5 C6 C7 C8 -179.5(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C7 C8 C9 C10 -0.6(6) . . . . ? C7 C8 C9 Br1 177.8(2) . . . . ? C8 C9 C10 C11 0.5(7) . . . . ? Br1 C9 C10 C11 -177.9(4) . . . . ? C7 C6 C11 C10 -0.2(6) . . . . ? C5 C6 C11 C10 179.4(4) . . . . ? C9 C10 C11 C6 -0.1(7) . . . . ? O3 C4 C12 C13 -134.0(5) . . . . ? C12A C4 C12 C13 -9.9(10) . . . . ? C1 C4 C12 C13 113.8(6) . . . . ? O3 C4 C12A C13A 45.0(10) . . . . ? C1 C4 C12A C13A -83.8(9) . . . . ? C12 C4 C12A C13A -18.4(9) . . . . ? C15 O6 C14 O5 -5.3(5) . . . . ? C15 O6 C14 C1 172.2(2) . . . . ? O2 C1 C14 O5 -23.0(4) . . . . ? C4 C1 C14 O5 -146.7(3) . . . . ? C2 C1 C14 O5 89.2(4) . . . . ? O2 C1 C14 O6 159.4(2) . . . . ? C4 C1 C14 O6 35.7(4) . . . . ? C2 C1 C14 O6 -88.4(3) . . . . ? C14 O6 C15 C16 76.9(4) . . . . ? O1 C2 C17 C22 -149.0(3) . . . . ? C1 C2 C17 C22 96.4(4) . . . . ? O1 C2 C17 C18 32.7(5) . . . . ? C1 C2 C17 C18 -82.0(4) . . . . ? C22 C17 C18 C19 1.1(6) . . . . ? C2 C17 C18 C19 179.5(3) . . . . ? C17 C18 C19 C20 -0.8(6) . . . . ? C18 C19 C20 C21 -0.4(5) . . . . ? C19 C20 C21 C22 1.4(5) . . . . ? C20 C21 C22 C17 -1.2(5) . . . . ? C18 C17 C22 C21 -0.1(5) . . . . ? C2 C17 C22 C21 -178.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.295 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.062