# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Yong Qiang Tu' _publ_contact_author_name 'Hongwei Liu' _publ_contact_author_email lihui4551830@126.com data_p21 _database_code_depnum_ccdc_archive 'CCDC 821778' #TrackingRef '- P21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Br O' _chemical_formula_weight 303.19 _chemical_absolute_configuration none 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.363(5) _cell_length_b 6.388(3) _cell_length_c 17.867(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.728(4) _cell_angle_gamma 90.00 _cell_volume 1394.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2223 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 19.12 _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4020 _exptl_absorpt_correction_T_max 0.6674 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9910 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.20 _reflns_number_total 4988 _reflns_number_gt 3222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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' _refine_ls_abs_structure_Flack 0.018(11) _refine_ls_number_reflns 4988 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 0.96605(5) 0.66407(11) 0.78448(3) 0.0713(2) Uani 1 1 d . . . Br2 Br 0.77857(5) -0.19424(9) 0.23792(3) 0.0704(2) Uani 1 1 d . . . C1 C 0.4671(5) 0.9116(9) 0.8629(3) 0.0513(15) Uani 1 1 d . . . H1 H 0.4717 1.0388 0.8382 0.062 Uiso 1 1 calc R . . C2 C 0.3724(5) 0.8606(10) 0.8917(3) 0.0612(18) Uani 1 1 d . . . H2 H 0.3153 0.9563 0.8889 0.073 Uiso 1 1 calc R . . C3 C 0.3635(5) 0.6684(13) 0.9245(3) 0.0668(16) Uani 1 1 d . . . H3 H 0.2983 0.6303 0.9408 0.080 Uiso 1 1 calc R . . C4 C 0.4499(5) 0.5324(10) 0.9332(3) 0.0564(15) Uani 1 1 d . . . H4 H 0.4447 0.4051 0.9577 0.068 Uiso 1 1 calc R . . C5 C 0.5455(4) 0.5850(8) 0.9054(3) 0.0494(15) Uani 1 1 d . . . H5 H 0.6036 0.4909 0.9105 0.059 Uiso 1 1 calc R . . C6 C 0.5551(4) 0.7740(8) 0.8705(3) 0.0381(13) Uani 1 1 d . . . C7 C 0.6550(4) 0.8463(7) 0.8390(3) 0.0442(13) Uani 1 1 d . . . C8 C 0.7516(4) 0.6936(7) 0.8329(3) 0.0410(12) Uani 1 1 d . . . C9 C 0.8030(3) 0.6359(8) 0.9132(3) 0.0380(12) Uani 1 1 d . . . C10 C 0.8167(4) 0.7877(9) 0.9687(3) 0.0464(13) Uani 1 1 d . . . H10 H 0.7930 0.9234 0.9566 0.056 Uiso 1 1 calc R . . C11 C 0.8647(5) 0.7433(10) 1.0416(3) 0.0562(18) Uani 1 1 d . . . H11 H 0.8752 0.8499 1.0774 0.067 Uiso 1 1 calc R . . C12 C 0.8971(5) 0.5441(12) 1.0618(4) 0.0609(17) Uani 1 1 d . . . H12 H 0.9261 0.5128 1.1116 0.073 Uiso 1 1 calc R . . C13 C 0.8860(4) 0.3899(9) 1.0069(4) 0.0597(17) Uani 1 1 d . . . H13 H 0.9105 0.2549 1.0195 0.072 Uiso 1 1 calc R . . C14 C 0.8383(4) 0.4353(8) 0.9325(3) 0.0487(14) Uani 1 1 d . . . H14 H 0.8303 0.3302 0.8960 0.058 Uiso 1 1 calc R . . C15 C 0.8340(4) 0.8263(9) 0.7957(3) 0.0522(14) Uani 1 1 d . . . H15A H 0.8547 0.9489 0.8266 0.063 Uiso 1 1 calc R . . H15B H 0.7992 0.8737 0.7463 0.063 Uiso 1 1 calc R . . C16 C 0.7091(4) 0.5132(8) 0.7804(3) 0.0553(15) Uani 1 1 d . . . H16A H 0.7698 0.4332 0.7682 0.083 Uiso 1 1 calc R . . H16B H 0.6680 0.5683 0.7348 0.083 Uiso 1 1 calc R . . H16C H 0.6629 0.4248 0.8053 0.083 Uiso 1 1 calc R . . C17 C 0.8957(5) -0.0524(10) 0.5289(4) 0.0621(16) Uani 1 1 d . . . H17 H 0.9138 -0.1854 0.5137 0.075 Uiso 1 1 calc R . . C18 C 0.9504(5) 0.0326(13) 0.5959(4) 0.079(2) Uani 1 1 d . . . H18 H 1.0043 -0.0452 0.6256 0.095 Uiso 1 1 calc R . . C19 C 0.9260(6) 0.2279(12) 0.6184(4) 0.080(2) Uani 1 1 d . . . H19 H 0.9633 0.2835 0.6631 0.096 Uiso 1 1 calc R . . C20 C 0.8465(5) 0.3423(11) 0.5753(4) 0.0707(19) Uani 1 1 d . . . H20 H 0.8290 0.4754 0.5909 0.085 Uiso 1 1 calc R . . C21 C 0.7918(4) 0.2598(8) 0.5083(3) 0.0529(16) Uani 1 1 d . . . H21 H 0.7391 0.3401 0.4785 0.063 Uiso 1 1 calc R . . C22 C 0.8143(4) 0.0611(8) 0.4851(3) 0.0427(14) Uani 1 1 d . . . C23 C 0.7537(4) -0.0442(8) 0.4171(3) 0.0435(14) Uani 1 1 d . . . C24 C 0.6983(4) 0.0841(7) 0.3484(3) 0.0354(12) Uani 1 1 d . . . C25 C 0.5914(4) 0.1799(9) 0.3692(3) 0.0413(12) Uani 1 1 d . . . C26 C 0.5267(5) 0.0654(10) 0.4111(3) 0.0597(17) Uani 1 1 d . . . H26 H 0.5484 -0.0673 0.4288 0.072 Uiso 1 1 calc R . . C27 C 0.4277(5) 0.1520(18) 0.4265(4) 0.087(2) Uani 1 1 d . . . H27 H 0.3836 0.0766 0.4546 0.104 Uiso 1 1 calc R . . C28 C 0.3968(6) 0.3443(16) 0.4004(5) 0.087(3) Uani 1 1 d . . . H28 H 0.3316 0.4009 0.4112 0.105 Uiso 1 1 calc R . . C29 C 0.4602(6) 0.4578(12) 0.3582(4) 0.078(2) Uani 1 1 d . . . H29 H 0.4377 0.5894 0.3398 0.094 Uiso 1 1 calc R . . C30 C 0.5571(5) 0.3746(9) 0.3437(3) 0.0540(16) Uani 1 1 d . . . H30 H 0.6006 0.4522 0.3158 0.065 Uiso 1 1 calc R . . C31 C 0.6592(4) -0.0615(8) 0.2825(3) 0.0528(15) Uani 1 1 d . . . H31A H 0.6135 0.0174 0.2434 0.063 Uiso 1 1 calc R . . H31B H 0.6142 -0.1704 0.2999 0.063 Uiso 1 1 calc R . . C32 C 0.7773(4) 0.2476(7) 0.3267(3) 0.0482(15) Uani 1 1 d . . . H32A H 0.8462 0.1826 0.3227 0.072 Uiso 1 1 calc R . . H32B H 0.7879 0.3549 0.3647 0.072 Uiso 1 1 calc R . . H32C H 0.7477 0.3086 0.2788 0.072 Uiso 1 1 calc R . . O1 O 0.6608(3) 1.0248(6) 0.8190(2) 0.0733(12) Uani 1 1 d . . . O2 O 0.7469(3) -0.2352(6) 0.4158(2) 0.0695(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0681(4) 0.0833(5) 0.0691(4) -0.0126(4) 0.0319(3) -0.0013(4) Br2 0.0862(5) 0.0641(4) 0.0651(4) -0.0174(4) 0.0253(3) 0.0048(4) C1 0.057(4) 0.044(3) 0.051(4) 0.010(3) 0.004(3) 0.008(3) C2 0.046(4) 0.077(5) 0.062(4) 0.000(4) 0.012(3) 0.020(3) C3 0.053(4) 0.088(5) 0.062(4) 0.010(4) 0.017(3) -0.012(4) C4 0.057(4) 0.061(4) 0.051(4) 0.017(3) 0.008(3) -0.005(3) C5 0.039(3) 0.055(4) 0.053(4) 0.010(3) 0.004(3) -0.003(3) C6 0.041(3) 0.031(3) 0.040(3) 0.003(3) -0.001(2) 0.002(3) C7 0.063(4) 0.025(3) 0.044(3) 0.008(2) 0.004(3) -0.005(3) C8 0.052(3) 0.030(3) 0.042(3) 0.002(3) 0.011(2) 0.001(3) C9 0.035(3) 0.033(3) 0.047(3) 0.003(3) 0.011(2) 0.000(3) C10 0.046(3) 0.045(3) 0.049(4) -0.001(3) 0.007(3) 0.009(3) C11 0.054(4) 0.070(5) 0.044(4) -0.008(3) 0.005(3) -0.006(3) C12 0.048(4) 0.089(5) 0.047(4) 0.014(4) 0.011(3) 0.004(4) C13 0.044(4) 0.061(4) 0.074(5) 0.024(4) 0.012(3) 0.014(3) C14 0.049(4) 0.049(3) 0.051(4) -0.004(3) 0.016(3) 0.007(3) C15 0.063(4) 0.045(3) 0.049(3) -0.001(3) 0.009(3) -0.002(3) C16 0.068(4) 0.045(3) 0.052(4) 0.001(3) 0.006(3) -0.006(3) C17 0.061(4) 0.067(4) 0.060(4) 0.001(4) 0.012(3) 0.014(3) C18 0.065(5) 0.110(6) 0.058(5) 0.012(4) -0.008(4) 0.027(4) C19 0.069(5) 0.102(7) 0.063(5) -0.019(4) -0.009(4) 0.006(4) C20 0.070(5) 0.070(5) 0.068(5) -0.022(4) -0.002(4) 0.010(4) C21 0.052(4) 0.054(4) 0.049(4) -0.010(3) -0.005(3) 0.012(3) C22 0.040(3) 0.047(3) 0.041(3) 0.005(3) 0.010(3) 0.005(3) C23 0.048(4) 0.035(3) 0.048(4) -0.002(3) 0.011(3) 0.000(3) C24 0.034(3) 0.035(3) 0.038(3) -0.002(2) 0.010(2) -0.004(2) C25 0.040(3) 0.046(3) 0.036(3) -0.007(3) 0.001(2) -0.010(3) C26 0.058(4) 0.075(4) 0.046(4) 0.011(3) 0.008(3) -0.011(3) C27 0.053(5) 0.153(8) 0.057(5) -0.016(6) 0.019(3) -0.028(6) C28 0.054(5) 0.138(9) 0.070(5) -0.043(5) 0.006(4) 0.016(5) C29 0.077(5) 0.078(5) 0.080(5) -0.019(4) 0.011(4) 0.014(4) C30 0.050(4) 0.053(4) 0.060(4) -0.004(3) 0.010(3) 0.003(3) C31 0.052(4) 0.057(3) 0.050(4) -0.013(3) 0.011(3) -0.003(3) C32 0.052(3) 0.042(3) 0.052(4) -0.003(2) 0.013(3) -0.010(2) O1 0.066(3) 0.039(2) 0.118(4) 0.026(2) 0.025(2) 0.001(2) O2 0.103(3) 0.042(3) 0.062(3) 0.005(2) 0.006(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C15 1.969(5) . ? Br2 C31 1.972(5) . ? C1 C2 1.388(8) . ? C1 C6 1.389(7) . ? C1 H1 0.9300 . ? C2 C3 1.371(9) . ? C2 H2 0.9300 . ? C3 C4 1.367(8) . ? C3 H3 0.9300 . ? C4 C5 1.392(7) . ? C4 H4 0.9300 . ? C5 C6 1.372(7) . ? C5 H5 0.9300 . ? C6 C7 1.506(7) . ? C7 O1 1.200(5) . ? C7 C8 1.558(6) . ? C8 C9 1.523(6) . ? C8 C16 1.527(7) . ? C8 C15 1.551(7) . ? C9 C10 1.379(7) . ? C9 C14 1.380(7) . ? C10 C11 1.377(7) . ? C10 H10 0.9300 . ? C11 C12 1.366(8) . ? C11 H11 0.9300 . ? C12 C13 1.382(8) . ? C12 H12 0.9300 . ? C13 C14 1.402(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.383(7) . ? C17 C18 1.393(8) . ? C17 H17 0.9300 . ? C18 C19 1.359(9) . ? C18 H18 0.9300 . ? C19 C20 1.365(8) . ? C19 H19 0.9300 . ? C20 C21 1.387(7) . ? C20 H20 0.9300 . ? C21 C22 1.377(6) . ? C21 H21 0.9300 . ? C22 C23 1.488(7) . ? C23 O2 1.223(6) . ? C23 C24 1.546(7) . ? C24 C32 1.520(6) . ? C24 C31 1.520(6) . ? C24 C25 1.552(6) . ? C25 C30 1.369(7) . ? C25 C26 1.384(7) . ? C26 C27 1.408(9) . ? C26 H26 0.9300 . ? C27 C28 1.348(11) . ? C27 H27 0.9300 . ? C28 C29 1.374(10) . ? C28 H28 0.9300 . ? C29 C30 1.370(8) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.5(5) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C3 C2 C1 119.7(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.3(6) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.8(6) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.8(5) . . ? C5 C6 C7 124.9(5) . . ? C1 C6 C7 116.4(5) . . ? O1 C7 C6 119.5(5) . . ? O1 C7 C8 119.5(5) . . ? C6 C7 C8 121.0(4) . . ? C9 C8 C16 116.8(4) . . ? C9 C8 C15 109.2(4) . . ? C16 C8 C15 109.7(4) . . ? C9 C8 C7 107.5(4) . . ? C16 C8 C7 108.6(4) . . ? C15 C8 C7 104.4(4) . . ? C10 C9 C14 118.3(5) . . ? C10 C9 C8 119.7(4) . . ? C14 C9 C8 122.0(5) . . ? C11 C10 C9 121.6(5) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C12 C11 C10 120.6(6) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 118.9(6) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 120.0(5) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C8 C15 Br1 111.4(4) . . ? C8 C15 H15A 109.4 . . ? Br1 C15 H15A 109.4 . . ? C8 C15 H15B 109.4 . . ? Br1 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 119.9(6) . . ? C22 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 120.8(6) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 119.9(6) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 119.9(6) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 121.1(6) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C17 118.4(5) . . ? C21 C22 C23 124.3(5) . . ? C17 C22 C23 117.3(5) . . ? O2 C23 C22 119.4(5) . . ? O2 C23 C24 119.5(5) . . ? C22 C23 C24 121.0(4) . . ? C32 C24 C31 111.3(4) . . ? C32 C24 C23 110.0(4) . . ? C31 C24 C23 109.9(4) . . ? C32 C24 C25 113.2(4) . . ? C31 C24 C25 104.1(4) . . ? C23 C24 C25 108.1(4) . . ? C30 C25 C26 119.0(5) . . ? C30 C25 C24 120.7(5) . . ? C26 C25 C24 120.2(5) . . ? C25 C26 C27 119.2(7) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 120.0(7) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 121.0(7) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C30 C29 C28 119.1(7) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? C25 C30 C29 121.6(6) . . ? C25 C30 H30 119.2 . . ? C29 C30 H30 119.2 . . ? C24 C31 Br2 114.0(3) . . ? C24 C31 H31A 108.8 . . ? Br2 C31 H31A 108.8 . . ? C24 C31 H31B 108.8 . . ? Br2 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C24 C32 H32A 109.5 . . ? C24 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C24 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C6 C1 C2 C3 -3.5(8) . . . . ? C1 C2 C3 C4 4.3(9) . . . . ? C2 C3 C4 C5 -3.2(9) . . . . ? C3 C4 C5 C6 1.4(8) . . . . ? C4 C5 C6 C1 -0.6(7) . . . . ? C4 C5 C6 C7 179.6(5) . . . . ? C2 C1 C6 C5 1.6(8) . . . . ? C2 C1 C6 C7 -178.5(5) . . . . ? C5 C6 C7 O1 -169.9(5) . . . . ? C1 C6 C7 O1 10.3(7) . . . . ? C5 C6 C7 C8 9.4(7) . . . . ? C1 C6 C7 C8 -170.5(4) . . . . ? O1 C7 C8 C9 113.3(5) . . . . ? C6 C7 C8 C9 -66.0(5) . . . . ? O1 C7 C8 C16 -119.5(5) . . . . ? C6 C7 C8 C16 61.2(6) . . . . ? O1 C7 C8 C15 -2.6(6) . . . . ? C6 C7 C8 C15 178.1(4) . . . . ? C16 C8 C9 C10 -163.1(4) . . . . ? C15 C8 C9 C10 71.8(5) . . . . ? C7 C8 C9 C10 -40.8(5) . . . . ? C16 C8 C9 C14 17.9(6) . . . . ? C15 C8 C9 C14 -107.2(5) . . . . ? C7 C8 C9 C14 140.2(5) . . . . ? C14 C9 C10 C11 0.3(7) . . . . ? C8 C9 C10 C11 -178.7(4) . . . . ? C9 C10 C11 C12 -2.2(8) . . . . ? C10 C11 C12 C13 3.3(9) . . . . ? C11 C12 C13 C14 -2.6(8) . . . . ? C10 C9 C14 C13 0.4(7) . . . . ? C8 C9 C14 C13 179.4(4) . . . . ? C12 C13 C14 C9 0.8(8) . . . . ? C9 C8 C15 Br1 64.0(4) . . . . ? C16 C8 C15 Br1 -65.1(5) . . . . ? C7 C8 C15 Br1 178.7(3) . . . . ? C22 C17 C18 C19 -0.9(10) . . . . ? C17 C18 C19 C20 0.4(11) . . . . ? C18 C19 C20 C21 -0.8(11) . . . . ? C19 C20 C21 C22 1.7(9) . . . . ? C20 C21 C22 C17 -2.2(8) . . . . ? C20 C21 C22 C23 175.2(5) . . . . ? C18 C17 C22 C21 1.8(8) . . . . ? C18 C17 C22 C23 -175.8(5) . . . . ? C21 C22 C23 O2 -151.5(6) . . . . ? C17 C22 C23 O2 26.0(8) . . . . ? C21 C22 C23 C24 27.9(7) . . . . ? C17 C22 C23 C24 -154.6(5) . . . . ? O2 C23 C24 C32 -132.9(5) . . . . ? C22 C23 C24 C32 47.6(6) . . . . ? O2 C23 C24 C31 -10.0(6) . . . . ? C22 C23 C24 C31 170.6(4) . . . . ? O2 C23 C24 C25 103.0(5) . . . . ? C22 C23 C24 C25 -76.4(5) . . . . ? C32 C24 C25 C30 22.3(6) . . . . ? C31 C24 C25 C30 -98.8(5) . . . . ? C23 C24 C25 C30 144.4(5) . . . . ? C32 C24 C25 C26 -160.6(5) . . . . ? C31 C24 C25 C26 78.3(5) . . . . ? C23 C24 C25 C26 -38.5(6) . . . . ? C30 C25 C26 C27 -0.1(8) . . . . ? C24 C25 C26 C27 -177.3(5) . . . . ? C25 C26 C27 C28 0.1(10) . . . . ? C26 C27 C28 C29 0.5(11) . . . . ? C27 C28 C29 C30 -1.0(10) . . . . ? C26 C25 C30 C29 -0.4(8) . . . . ? C24 C25 C30 C29 176.8(5) . . . . ? C28 C29 C30 C25 1.0(9) . . . . ? C32 C24 C31 Br2 53.6(5) . . . . ? C23 C24 C31 Br2 -68.6(4) . . . . ? C25 C24 C31 Br2 175.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.492 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.056