# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Alexander Kornienko' _publ_contact_author_email akornien@nmt.edu loop_ _publ_author_name 'Igor Magedov' 'Nikolai Evdokimov' 'Menuka Karki' 'Amanda Peretti' 'Dustin Lima' 'Lilia Frolova' 'Mary Reisenauer' 'Anntherese Romero' 'Paul Tongwa' 'Alexandr Fonari' 'Jeff Altig' 'Snezna Rogelj' 'Mikhail Antipin' 'Charles Shuster' 'Alexander Kornienko' data_11 _database_code_depnum_ccdc_archive 'CCDC 873143' #TrackingRef '- 11-18-19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Br2 O3' _chemical_formula_sum 'C22 H16 Br2 O3' _chemical_formula_weight 488.17 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 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc ' 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' '-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 18.738(7) _cell_length_b 11.950(5) _cell_length_c 16.831(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.958(9) _cell_angle_gamma 90.00 _cell_volume 3760(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2449 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 18.96 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 4.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6965 _exptl_absorpt_correction_T_max 0.7513 _exptl_absorpt_process_details SADABS _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21882 _diffrn_reflns_av_R_equivalents 0.0794 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3311 _reflns_number_gt 2148 _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^)+(0.0272P)^2^+24.1348P] 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 3311 _refine_ls_number_parameters 248 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _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 0.85325(4) 0.32428(6) 0.02199(4) 0.0684(2) Uani 1 1 d . . . Br2 Br 0.95788(5) 0.75570(7) 0.10077(6) 0.0994(3) Uani 1 1 d . . . O1 O 0.7790(3) 0.7103(3) 0.3158(3) 0.0727(14) Uani 1 1 d . . . O2 O 0.6809(3) 0.6035(3) 0.3133(2) 0.0656(12) Uani 1 1 d . . . O3 O 0.7303(3) 0.3275(4) 0.4404(2) 0.0643(12) Uani 1 1 d D . . H3 H 0.6859(12) 0.311(7) 0.443(5) 0.11(3) Uiso 1 1 d D . . C1 C 0.7989(3) 0.0846(4) 0.3933(3) 0.0447(14) Uani 1 1 d . . . H1A H 0.7495 0.1026 0.3931 0.054 Uiso 1 1 calc R . . C2 C 0.8209(4) -0.0237(5) 0.4092(4) 0.0628(18) Uani 1 1 d . . . H2A H 0.7867 -0.0798 0.4191 0.075 Uiso 1 1 calc R . . C3 C 0.8928(4) -0.0506(6) 0.4109(5) 0.081(2) Uani 1 1 d . . . H3A H 0.9077 -0.1251 0.4226 0.097 Uiso 1 1 calc R . . C4 C 0.9421(4) 0.0281(6) 0.3961(5) 0.076(2) Uani 1 1 d . . . H4A H 0.9912 0.0082 0.3977 0.092 Uiso 1 1 calc R . . C5 C 0.9215(3) 0.1392(5) 0.3784(4) 0.0535(15) Uani 1 1 d . . . C6 C 0.8482(3) 0.1688(4) 0.3774(3) 0.0376(12) Uani 1 1 d . . . C7 C 0.9728(3) 0.2222(5) 0.3615(5) 0.075(2) Uani 1 1 d . . . H7A H 1.0218 0.2022 0.3602 0.090 Uiso 1 1 calc R . . C8 C 0.9522(3) 0.3289(5) 0.3475(4) 0.0554(16) Uani 1 1 d . . . H8A H 0.9874 0.3840 0.3389 0.066 Uiso 1 1 calc R . . C9 C 0.8789(3) 0.3605(4) 0.3454(3) 0.0420(13) Uani 1 1 d . . . C10 C 0.8273(3) 0.2838(4) 0.3599(3) 0.0360(12) Uani 1 1 d . . . C11 C 0.8625(3) 0.4822(4) 0.3225(3) 0.0472(14) Uani 1 1 d . . . H11A H 0.8967 0.5308 0.3550 0.057 Uiso 1 1 calc R . . C12 C 0.7876(3) 0.5099(4) 0.3454(3) 0.0440(14) Uani 1 1 d . . . H12A H 0.7894 0.5060 0.4049 0.053 Uiso 1 1 calc R . . C13 C 0.7338(3) 0.4238(4) 0.3157(3) 0.0401(13) Uani 1 1 d . . . H13A H 0.7391 0.4110 0.2577 0.048 Uiso 1 1 calc R . . C14 C 0.7482(3) 0.3140(4) 0.3599(3) 0.0400(12) Uani 1 1 d . . . H14A H 0.7185 0.2531 0.3339 0.048 Uiso 1 1 calc R . . C15 C 0.7517(4) 0.6196(5) 0.3228(3) 0.0576(17) Uani 1 1 d . . . C16 C 0.6635(3) 0.4863(5) 0.3252(4) 0.0568(16) Uani 1 1 d . . . H16A H 0.6259 0.4610 0.2849 0.068 Uiso 1 1 calc R . . H16B H 0.6465 0.4742 0.3789 0.068 Uiso 1 1 calc R . . C17 C 0.8750(3) 0.5018(4) 0.2344(3) 0.0428(13) Uani 1 1 d . . . C18 C 0.8604(3) 0.4193(5) 0.1775(3) 0.0434(13) Uani 1 1 d . . . H18A H 0.8412 0.3495 0.1927 0.052 Uiso 1 1 calc R . . C19 C 0.8737(3) 0.4385(5) 0.0987(3) 0.0486(14) Uani 1 1 d . . . C20 C 0.9017(3) 0.5389(5) 0.0741(4) 0.0582(17) Uani 1 1 d . . . H20A H 0.9103 0.5520 0.0199 0.070 Uiso 1 1 calc R . . C21 C 0.9165(3) 0.6190(5) 0.1316(4) 0.0574(17) Uani 1 1 d . . . C22 C 0.9038(3) 0.6029(5) 0.2108(4) 0.0506(15) Uani 1 1 d . . . H22A H 0.9145 0.6603 0.2487 0.061 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 0.0919(5) 0.0664(4) 0.0468(4) -0.0077(3) 0.0037(3) 0.0209(4) Br2 0.1060(7) 0.0622(5) 0.1362(8) 0.0306(5) 0.0525(6) -0.0171(5) O1 0.126(4) 0.030(2) 0.063(3) 0.005(2) 0.016(3) 0.010(2) O2 0.087(4) 0.045(3) 0.065(3) 0.011(2) 0.012(2) 0.023(2) O3 0.082(4) 0.067(3) 0.047(2) 0.011(2) 0.022(2) 0.022(3) C1 0.050(4) 0.036(3) 0.048(3) 0.004(2) 0.003(3) 0.003(3) C2 0.066(4) 0.039(3) 0.085(5) 0.011(3) 0.017(4) -0.001(3) C3 0.067(5) 0.045(4) 0.131(7) 0.028(4) 0.018(5) 0.020(4) C4 0.050(4) 0.056(4) 0.123(6) 0.030(4) 0.012(4) 0.018(3) C5 0.054(4) 0.043(3) 0.063(4) 0.010(3) 0.001(3) 0.004(3) C6 0.045(3) 0.032(3) 0.035(3) 0.002(2) 0.000(2) 0.003(2) C7 0.041(4) 0.054(4) 0.129(7) 0.021(4) 0.004(4) 0.002(3) C8 0.046(4) 0.044(3) 0.075(4) 0.011(3) -0.003(3) -0.009(3) C9 0.055(4) 0.034(3) 0.036(3) 0.002(2) -0.002(3) 0.000(3) C10 0.045(3) 0.032(3) 0.031(3) 0.000(2) -0.004(2) 0.000(2) C11 0.061(4) 0.037(3) 0.043(3) 0.000(2) -0.005(3) -0.011(3) C12 0.068(4) 0.034(3) 0.030(3) 0.003(2) 0.003(3) 0.002(3) C13 0.052(4) 0.036(3) 0.032(3) 0.006(2) 0.001(2) 0.007(3) C14 0.050(3) 0.035(3) 0.036(3) 0.005(2) 0.004(2) 0.005(2) C15 0.097(6) 0.035(4) 0.042(3) 0.001(3) 0.014(3) 0.011(4) C16 0.064(4) 0.048(4) 0.059(4) 0.013(3) 0.008(3) 0.015(3) C17 0.045(3) 0.034(3) 0.049(3) 0.007(3) 0.000(3) 0.002(2) C18 0.047(3) 0.038(3) 0.046(3) 0.007(3) 0.005(3) 0.001(3) C19 0.048(4) 0.049(4) 0.050(4) 0.001(3) 0.007(3) 0.013(3) C20 0.065(4) 0.057(4) 0.055(4) 0.021(3) 0.022(3) 0.015(3) C21 0.046(4) 0.044(4) 0.083(5) 0.019(3) 0.017(3) 0.000(3) C22 0.050(4) 0.039(3) 0.064(4) 0.007(3) 0.008(3) -0.006(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C19 1.899(6) . ? Br2 C21 1.896(6) . ? O1 C15 1.208(7) . ? O2 C15 1.340(8) . ? O2 C16 1.455(7) . ? O3 C14 1.427(6) . ? O3 H3 0.8600(11) . ? C1 C2 1.379(8) . ? C1 C6 1.405(7) . ? C1 H1A 0.9500 . ? C2 C3 1.383(9) . ? C2 H2A 0.9500 . ? C3 C4 1.353(9) . ? C3 H3A 0.9500 . ? C4 C5 1.408(8) . ? C4 H4A 0.9500 . ? C5 C6 1.417(8) . ? C5 C7 1.423(8) . ? C6 C10 1.454(7) . ? C7 C8 1.348(8) . ? C7 H7A 0.9500 . ? C8 C9 1.424(8) . ? C8 H8A 0.9500 . ? C9 C10 1.366(7) . ? C9 C11 1.531(7) . ? C10 C14 1.525(7) . ? C11 C12 1.517(8) . ? C11 C17 1.534(7) . ? C11 H11A 1.0000 . ? C12 C13 1.502(7) . ? C12 C15 1.509(8) . ? C12 H12A 1.0000 . ? C13 C14 1.522(7) . ? C13 C16 1.533(7) . ? C13 H13A 1.0000 . ? C14 H14A 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.389(7) . ? C17 C22 1.391(7) . ? C18 C19 1.386(7) . ? C18 H18A 0.9500 . ? C19 C20 1.385(8) . ? C20 C21 1.376(9) . ? C20 H20A 0.9500 . ? C21 C22 1.383(8) . ? C22 H22A 0.9500 . ? 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 C15 O2 C16 110.5(5) . . ? C14 O3 H3 108(6) . . ? C2 C1 C6 121.1(5) . . ? C2 C1 H1A 119.4 . . ? C6 C1 H1A 119.4 . . ? C1 C2 C3 120.0(6) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.7(6) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.9(6) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 119.3(6) . . ? C4 C5 C7 121.3(6) . . ? C6 C5 C7 119.4(5) . . ? C1 C6 C5 117.9(5) . . ? C1 C6 C10 122.9(5) . . ? C5 C6 C10 119.1(5) . . ? C8 C7 C5 120.3(6) . . ? C8 C7 H7A 119.8 . . ? C5 C7 H7A 119.8 . . ? C7 C8 C9 121.3(6) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C10 C9 C8 120.8(5) . . ? C10 C9 C11 123.4(5) . . ? C8 C9 C11 115.8(5) . . ? C9 C10 C6 119.1(5) . . ? C9 C10 C14 122.7(5) . . ? C6 C10 C14 118.2(4) . . ? C12 C11 C9 108.5(4) . . ? C12 C11 C17 114.7(4) . . ? C9 C11 C17 110.3(4) . . ? C12 C11 H11A 107.7 . . ? C9 C11 H11A 107.7 . . ? C17 C11 H11A 107.7 . . ? C13 C12 C15 103.5(5) . . ? C13 C12 C11 112.1(4) . . ? C15 C12 C11 121.9(5) . . ? C13 C12 H12A 106.1 . . ? C15 C12 H12A 106.1 . . ? C11 C12 H12A 106.1 . . ? C12 C13 C14 109.6(4) . . ? C12 C13 C16 101.1(4) . . ? C14 C13 C16 119.6(5) . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? C16 C13 H13A 108.6 . . ? O3 C14 C13 108.8(4) . . ? O3 C14 C10 108.6(4) . . ? C13 C14 C10 110.1(4) . . ? O3 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? C10 C14 H14A 109.8 . . ? O1 C15 O2 122.6(6) . . ? O1 C15 C12 128.3(7) . . ? O2 C15 C12 109.1(5) . . ? O2 C16 C13 104.6(5) . . ? O2 C16 H16A 110.8 . . ? C13 C16 H16A 110.8 . . ? O2 C16 H16B 110.8 . . ? C13 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C18 C17 C22 118.7(5) . . ? C18 C17 C11 121.4(5) . . ? C22 C17 C11 119.8(5) . . ? C19 C18 C17 120.2(5) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C20 C19 C18 121.8(6) . . ? C20 C19 Br1 118.8(4) . . ? C18 C19 Br1 119.4(4) . . ? C21 C20 C19 117.0(5) . . ? C21 C20 H20A 121.5 . . ? C19 C20 H20A 121.5 . . ? C20 C21 C22 122.8(5) . . ? C20 C21 Br2 118.2(5) . . ? C22 C21 Br2 119.0(5) . . ? C21 C22 C17 119.5(6) . . ? C21 C22 H22A 120.2 . . ? C17 C22 H22A 120.2 . . ? 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 _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 1.0(10) . . . . ? C1 C2 C3 C4 -0.8(12) . . . . ? C2 C3 C4 C5 -0.2(13) . . . . ? C3 C4 C5 C6 1.0(11) . . . . ? C3 C4 C5 C7 -179.0(7) . . . . ? C2 C1 C6 C5 -0.2(8) . . . . ? C2 C1 C6 C10 179.7(5) . . . . ? C4 C5 C6 C1 -0.8(9) . . . . ? C7 C5 C6 C1 179.2(6) . . . . ? C4 C5 C6 C10 179.4(6) . . . . ? C7 C5 C6 C10 -0.6(8) . . . . ? C4 C5 C7 C8 -177.6(7) . . . . ? C6 C5 C7 C8 2.4(10) . . . . ? C5 C7 C8 C9 -3.1(11) . . . . ? C7 C8 C9 C10 2.0(9) . . . . ? C7 C8 C9 C11 -175.4(6) . . . . ? C8 C9 C10 C6 -0.2(8) . . . . ? C11 C9 C10 C6 177.0(5) . . . . ? C8 C9 C10 C14 178.7(5) . . . . ? C11 C9 C10 C14 -4.1(8) . . . . ? C1 C6 C10 C9 179.7(5) . . . . ? C5 C6 C10 C9 -0.4(7) . . . . ? C1 C6 C10 C14 0.8(7) . . . . ? C5 C6 C10 C14 -179.4(5) . . . . ? C10 C9 C11 C12 18.5(7) . . . . ? C8 C9 C11 C12 -164.2(5) . . . . ? C10 C9 C11 C17 -108.0(6) . . . . ? C8 C9 C11 C17 69.3(6) . . . . ? C9 C11 C12 C13 -49.7(5) . . . . ? C17 C11 C12 C13 74.1(6) . . . . ? C9 C11 C12 C15 -173.1(5) . . . . ? C17 C11 C12 C15 -49.3(7) . . . . ? C15 C12 C13 C14 -158.7(4) . . . . ? C11 C12 C13 C14 68.1(5) . . . . ? C15 C12 C13 C16 -31.5(5) . . . . ? C11 C12 C13 C16 -164.7(4) . . . . ? C12 C13 C14 O3 70.0(6) . . . . ? C16 C13 C14 O3 -46.0(7) . . . . ? C12 C13 C14 C10 -48.9(5) . . . . ? C16 C13 C14 C10 -164.9(5) . . . . ? C9 C10 C14 O3 -99.9(6) . . . . ? C6 C10 C14 O3 79.0(6) . . . . ? C9 C10 C14 C13 19.1(7) . . . . ? C6 C10 C14 C13 -162.0(4) . . . . ? C16 O2 C15 O1 179.9(5) . . . . ? C16 O2 C15 C12 -2.0(6) . . . . ? C13 C12 C15 O1 -159.9(6) . . . . ? C11 C12 C15 O1 -32.5(9) . . . . ? C13 C12 C15 O2 22.2(6) . . . . ? C11 C12 C15 O2 149.5(5) . . . . ? C15 O2 C16 C13 -18.7(6) . . . . ? C12 C13 C16 O2 30.9(5) . . . . ? C14 C13 C16 O2 151.2(5) . . . . ? C12 C11 C17 C18 -87.8(6) . . . . ? C9 C11 C17 C18 35.0(7) . . . . ? C12 C11 C17 C22 94.3(6) . . . . ? C9 C11 C17 C22 -142.9(5) . . . . ? C22 C17 C18 C19 -0.6(8) . . . . ? C11 C17 C18 C19 -178.6(5) . . . . ? C17 C18 C19 C20 0.1(9) . . . . ? C17 C18 C19 Br1 180.0(4) . . . . ? C18 C19 C20 C21 0.6(9) . . . . ? Br1 C19 C20 C21 -179.3(4) . . . . ? C19 C20 C21 C22 -0.8(9) . . . . ? C19 C20 C21 Br2 178.0(4) . . . . ? C20 C21 C22 C17 0.3(9) . . . . ? Br2 C21 C22 C17 -178.5(4) . . . . ? C18 C17 C22 C21 0.4(8) . . . . ? C11 C17 C22 C21 178.4(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.071 _refine_diff_density_min -0.945 _refine_diff_density_rms 0.078 _publ_section_references ; Bruker (2001). SAINTPlus for NT. Data Reduction and Correction Program v. 6.2, Bruker AXS, Madison, Wisconsin, USA. Bruker (2005). APEX2 software package. Bruker Molecular Analysis Research Tool, v. 1.27. Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2003). SADABS v.2.03, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (2001). SHELXTL NT v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; #===END data_18 _database_code_depnum_ccdc_archive 'CCDC 873144' #TrackingRef '- 11-18-19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Br2 O2' _chemical_formula_sum 'C22 H18 Br2 O2' _chemical_formula_weight 474.18 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.1515(13) _cell_length_b 10.698(2) _cell_length_c 24.150(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1847.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9950 _cell_measurement_theta_min 2.5430 _cell_measurement_theta_max 30.1864 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 4.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2720 _exptl_absorpt_correction_T_max 0.6673 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _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 SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29780 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 30.64 _reflns_number_total 5723 _reflns_number_gt 5240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _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^)+(0.0265P)^2^+0.5353P] 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 0.511(6) _refine_ls_number_reflns 5723 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0558 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration unk 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 -0.00798(3) 0.150492(17) 0.679302(7) 0.02088(5) Uani 1 1 d . . . Br2 Br -0.52163(4) -0.19444(2) 0.773002(9) 0.03654(7) Uani 1 1 d . . . O1 O 0.0937(2) -0.21524(13) 0.94216(6) 0.0244(3) Uani 1 1 d . . . O2 O -0.2140(2) -0.17644(15) 0.94405(6) 0.0245(3) Uani 1 1 d . . . C1 C 0.5455(3) 0.53830(18) 0.90651(8) 0.0202(4) Uani 1 1 d . . . H1 H 0.6159 0.6135 0.9087 0.024 Uiso 1 1 calc R . . C2 C 0.6162(3) 0.43478(19) 0.87843(8) 0.0191(4) Uani 1 1 d . . . H2 H 0.7336 0.4400 0.8602 0.023 Uiso 1 1 calc R . . C3 C 0.5151(3) 0.32421(15) 0.87710(7) 0.0156(3) Uani 1 1 d . . . H3 H 0.5658 0.2533 0.8588 0.019 Uiso 1 1 calc R . . C4 C 0.3388(2) 0.31555(17) 0.90251(7) 0.0131(3) Uani 1 1 d . . . C5 C 0.2296(2) 0.19778(17) 0.90084(7) 0.0126(3) Uani 1 1 d . . . C6 C 0.3131(3) 0.08581(18) 0.89990(8) 0.0153(3) Uani 1 1 d . . . H6 H 0.4457 0.0812 0.8990 0.018 Uiso 1 1 calc R . . C7 C 0.2010(3) -0.03177(18) 0.90024(8) 0.0166(4) Uani 1 1 d . . . H7 H 0.1758 -0.0573 0.8611 0.020 Uiso 1 1 calc R . . C8 C 0.2671(3) -0.1456(2) 0.93260(9) 0.0236(4) Uani 1 1 d . . . H8A H 0.3573 -0.1956 0.9108 0.028 Uiso 1 1 calc R . . H8B H 0.3261 -0.1208 0.9680 0.028 Uiso 1 1 calc R . . C9 C -0.0566(3) -0.13854(18) 0.93845(8) 0.0199(4) Uani 1 1 d . . . C10 C 0.0154(3) -0.00701(15) 0.92910(7) 0.0154(3) Uani 1 1 d . . . H10 H 0.0473 0.0267 0.9665 0.018 Uiso 1 1 calc R . . C11 C -0.0971(2) 0.09473(18) 0.90016(7) 0.0148(3) Uani 1 1 d . . . H11 H -0.2161 0.1069 0.9212 0.018 Uiso 1 1 calc R . . C12 C 0.0189(3) 0.21668(15) 0.90485(6) 0.0131(3) Uani 1 1 d . . . H12 H -0.0190 0.2721 0.8735 0.016 Uiso 1 1 calc R . . C13 C -0.0172(3) 0.28913(16) 0.95887(7) 0.0154(3) Uani 1 1 d . . . H13A H -0.1536 0.2982 0.9647 0.019 Uiso 1 1 calc R . . H13B H 0.0348 0.2419 0.9906 0.019 Uiso 1 1 calc R . . C14 C 0.0734(3) 0.41838(17) 0.95620(8) 0.0164(4) Uani 1 1 d . . . H14A H -0.0100 0.4750 0.9352 0.020 Uiso 1 1 calc R . . H14B H 0.0843 0.4517 0.9943 0.020 Uiso 1 1 calc R . . C15 C 0.2655(3) 0.42026(17) 0.92947(7) 0.0145(3) Uani 1 1 d . . . C16 C 0.3708(3) 0.52993(18) 0.93121(8) 0.0180(4) Uani 1 1 d . . . H16 H 0.3215 0.6009 0.9498 0.022 Uiso 1 1 calc R . . C17 C -0.1474(2) 0.05772(18) 0.84095(8) 0.0146(3) Uani 1 1 d . . . C18 C -0.2843(3) -0.03373(18) 0.83324(8) 0.0166(4) Uani 1 1 d . . . H18 H -0.3423 -0.0717 0.8644 0.020 Uiso 1 1 calc R . . C19 C -0.3356(3) -0.06907(19) 0.78027(8) 0.0206(4) Uani 1 1 d . . . C20 C -0.2564(3) -0.0159(2) 0.73352(8) 0.0206(4) Uani 1 1 d . . . H20 H -0.2943 -0.0397 0.6973 0.025 Uiso 1 1 calc R . . C21 C -0.1195(3) 0.07384(18) 0.74207(7) 0.0161(4) Uani 1 1 d . . . C22 C -0.0623(2) 0.11098(17) 0.79463(7) 0.0147(3) Uani 1 1 d . . . H22 H 0.0334 0.1718 0.7989 0.018 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 0.02496(9) 0.02360(9) 0.01406(7) 0.00072(6) 0.00299(8) -0.00112(8) Br2 0.03985(13) 0.04657(13) 0.02321(9) -0.00330(9) -0.00273(10) -0.02959(12) O1 0.0311(8) 0.0146(7) 0.0275(8) 0.0046(6) -0.0025(6) -0.0046(6) O2 0.0294(8) 0.0239(8) 0.0203(7) 0.0016(6) 0.0005(6) -0.0122(7) C1 0.0213(9) 0.0158(8) 0.0235(9) 0.0043(7) -0.0086(7) -0.0047(7) C2 0.0142(8) 0.0207(9) 0.0223(9) 0.0054(8) -0.0032(7) -0.0044(7) C3 0.0155(8) 0.0146(7) 0.0168(7) 0.0029(6) -0.0006(7) 0.0002(8) C4 0.0134(7) 0.0126(8) 0.0132(8) 0.0022(7) -0.0031(6) 0.0001(6) C5 0.0116(7) 0.0164(8) 0.0099(7) 0.0000(6) -0.0002(6) 0.0008(7) C6 0.0137(8) 0.0144(9) 0.0177(8) 0.0008(7) -0.0003(7) -0.0012(7) C7 0.0189(8) 0.0129(8) 0.0179(9) 0.0013(7) -0.0004(7) 0.0020(7) C8 0.0241(9) 0.0147(9) 0.0319(11) 0.0052(9) -0.0025(8) -0.0017(8) C9 0.0304(10) 0.0169(9) 0.0123(8) -0.0009(7) -0.0009(7) -0.0051(8) C10 0.0179(8) 0.0146(7) 0.0137(7) 0.0009(6) 0.0000(7) -0.0026(7) C11 0.0132(8) 0.0176(9) 0.0136(8) -0.0010(7) 0.0010(6) -0.0021(7) C12 0.0143(8) 0.0126(7) 0.0124(7) -0.0009(5) -0.0007(7) 0.0001(7) C13 0.0150(8) 0.0185(8) 0.0129(7) -0.0025(6) 0.0025(7) 0.0008(7) C14 0.0178(8) 0.0156(9) 0.0159(8) -0.0032(7) -0.0003(7) 0.0016(7) C15 0.0168(8) 0.0136(8) 0.0131(8) 0.0014(7) -0.0038(6) -0.0002(7) C16 0.0241(9) 0.0122(9) 0.0178(9) 0.0008(7) -0.0062(7) -0.0004(7) C17 0.0125(8) 0.0160(9) 0.0153(8) -0.0016(7) -0.0010(6) 0.0015(7) C18 0.0143(8) 0.0202(9) 0.0154(8) -0.0015(7) 0.0013(7) -0.0025(7) C19 0.0176(8) 0.0227(10) 0.0214(9) -0.0030(8) -0.0014(8) -0.0066(7) C20 0.0211(9) 0.0238(10) 0.0171(9) -0.0038(8) -0.0029(7) -0.0024(7) C21 0.0164(8) 0.0192(9) 0.0126(8) 0.0005(7) 0.0012(6) 0.0011(7) C22 0.0148(8) 0.0145(8) 0.0149(8) -0.0010(6) 0.0003(6) -0.0013(6) _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 C21 1.8988(19) . ? Br2 C19 1.8974(19) . ? O1 C9 1.355(3) . ? O1 C8 1.465(2) . ? O2 C9 1.204(2) . ? C1 C16 1.387(3) . ? C1 C2 1.393(3) . ? C1 H1 0.9500 . ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 C4 1.406(2) . ? C3 H3 0.9500 . ? C4 C15 1.398(3) . ? C4 C5 1.483(3) . ? C5 C6 1.339(3) . ? C5 C12 1.524(2) . ? C6 C7 1.491(3) . ? C6 H6 0.9500 . ? C7 C10 1.523(3) . ? C7 C8 1.523(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.515(3) . ? C10 C11 1.523(3) . ? C10 H10 1.0000 . ? C11 C17 1.527(2) . ? C11 C12 1.550(2) . ? C11 H11 1.0000 . ? C12 C13 1.539(2) . ? C12 H12 1.0000 . ? C13 C14 1.529(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.518(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.395(3) . ? C16 H16 0.9500 . ? C17 C22 1.395(3) . ? C17 C18 1.397(3) . ? C18 C19 1.383(3) . ? C18 H18 0.9500 . ? C19 C20 1.385(3) . ? C20 C21 1.387(3) . ? C20 H20 0.9500 . ? C21 C22 1.392(3) . ? C22 H22 0.9500 . ? 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 O1 C8 110.69(15) . . ? C16 C1 C2 118.99(18) . . ? C16 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 120.02(18) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.91(17) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C15 C4 C3 119.14(17) . . ? C15 C4 C5 119.75(16) . . ? C3 C4 C5 121.10(16) . . ? C6 C5 C4 121.73(15) . . ? C6 C5 C12 124.13(16) . . ? C4 C5 C12 113.97(15) . . ? C5 C6 C7 121.00(16) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C10 108.91(15) . . ? C6 C7 C8 120.73(16) . . ? C10 C7 C8 100.06(15) . . ? C6 C7 H7 108.8 . . ? C10 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? O1 C8 C7 102.99(16) . . ? O1 C8 H8A 111.2 . . ? C7 C8 H8A 111.2 . . ? O1 C8 H8B 111.2 . . ? C7 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? O2 C9 O1 122.00(19) . . ? O2 C9 C10 130.3(2) . . ? O1 C9 C10 107.62(16) . . ? C9 C10 C7 101.71(15) . . ? C9 C10 C11 123.53(17) . . ? C7 C10 C11 112.01(14) . . ? C9 C10 H10 106.1 . . ? C7 C10 H10 106.1 . . ? C11 C10 H10 106.1 . . ? C10 C11 C17 111.65(15) . . ? C10 C11 C12 106.58(14) . . ? C17 C11 C12 114.39(14) . . ? C10 C11 H11 108.0 . . ? C17 C11 H11 108.0 . . ? C12 C11 H11 108.0 . . ? C5 C12 C13 106.66(14) . . ? C5 C12 C11 114.38(14) . . ? C13 C12 C11 113.33(14) . . ? C5 C12 H12 107.4 . . ? C13 C12 H12 107.4 . . ? C11 C12 H12 107.4 . . ? C14 C13 C12 110.40(14) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C13 114.45(15) . . ? C15 C14 H14A 108.6 . . ? C13 C14 H14A 108.6 . . ? C15 C14 H14B 108.6 . . ? C13 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? C16 C15 C4 119.06(17) . . ? C16 C15 C14 119.14(17) . . ? C4 C15 C14 121.79(16) . . ? C1 C16 C15 121.84(19) . . ? C1 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C22 C17 C18 119.01(17) . . ? C22 C17 C11 122.83(16) . . ? C18 C17 C11 118.15(16) . . ? C19 C18 C17 120.03(18) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 122.22(18) . . ? C18 C19 Br2 117.68(15) . . ? C20 C19 Br2 120.10(15) . . ? C19 C20 C21 116.84(18) . . ? C19 C20 H20 121.6 . . ? C21 C20 H20 121.6 . . ? C20 C21 C22 122.74(18) . . ? C20 C21 Br1 118.46(14) . . ? C22 C21 Br1 118.79(14) . . ? C21 C22 C17 119.13(17) . . ? C21 C22 H22 120.4 . . ? C17 C22 H22 120.4 . . ? 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 C16 C1 C2 C3 -2.2(3) . . . . ? C1 C2 C3 C4 1.8(3) . . . . ? C2 C3 C4 C15 -0.1(3) . . . . ? C2 C3 C4 C5 179.55(16) . . . . ? C15 C4 C5 C6 -148.77(18) . . . . ? C3 C4 C5 C6 31.6(3) . . . . ? C15 C4 C5 C12 26.7(2) . . . . ? C3 C4 C5 C12 -152.91(15) . . . . ? C4 C5 C6 C7 177.82(17) . . . . ? C12 C5 C6 C7 2.8(3) . . . . ? C5 C6 C7 C10 -27.5(2) . . . . ? C5 C6 C7 C8 -142.24(19) . . . . ? C9 O1 C8 C7 -22.2(2) . . . . ? C6 C7 C8 O1 156.73(17) . . . . ? C10 C7 C8 O1 37.49(19) . . . . ? C8 O1 C9 O2 178.85(19) . . . . ? C8 O1 C9 C10 -3.4(2) . . . . ? O2 C9 C10 C7 -155.0(2) . . . . ? O1 C9 C10 C7 27.48(18) . . . . ? O2 C9 C10 C11 -28.4(3) . . . . ? O1 C9 C10 C11 154.10(16) . . . . ? C6 C7 C10 C9 -166.52(15) . . . . ? C8 C7 C10 C9 -38.98(17) . . . . ? C6 C7 C10 C11 59.7(2) . . . . ? C8 C7 C10 C11 -172.78(15) . . . . ? C9 C10 C11 C17 -60.2(2) . . . . ? C7 C10 C11 C17 61.8(2) . . . . ? C9 C10 C11 C12 174.24(15) . . . . ? C7 C10 C11 C12 -63.72(18) . . . . ? C6 C5 C12 C13 118.55(18) . . . . ? C4 C5 C12 C13 -56.83(18) . . . . ? C6 C5 C12 C11 -7.6(2) . . . . ? C4 C5 C12 C11 177.06(14) . . . . ? C10 C11 C12 C5 36.04(18) . . . . ? C17 C11 C12 C5 -87.84(18) . . . . ? C10 C11 C12 C13 -86.51(18) . . . . ? C17 C11 C12 C13 149.60(15) . . . . ? C5 C12 C13 C14 63.40(18) . . . . ? C11 C12 C13 C14 -169.86(15) . . . . ? C12 C13 C14 C15 -40.4(2) . . . . ? C3 C4 C15 C16 -1.1(3) . . . . ? C5 C4 C15 C16 179.28(16) . . . . ? C3 C4 C15 C14 178.09(16) . . . . ? C5 C4 C15 C14 -1.6(3) . . . . ? C13 C14 C15 C16 -171.87(16) . . . . ? C13 C14 C15 C4 9.0(2) . . . . ? C2 C1 C16 C15 1.0(3) . . . . ? C4 C15 C16 C1 0.6(3) . . . . ? C14 C15 C16 C1 -178.59(17) . . . . ? C10 C11 C17 C22 -107.1(2) . . . . ? C12 C11 C17 C22 14.1(2) . . . . ? C10 C11 C17 C18 72.7(2) . . . . ? C12 C11 C17 C18 -166.12(16) . . . . ? C22 C17 C18 C19 -0.9(3) . . . . ? C11 C17 C18 C19 179.31(18) . . . . ? C17 C18 C19 C20 -0.6(3) . . . . ? C17 C18 C19 Br2 179.70(14) . . . . ? C18 C19 C20 C21 1.2(3) . . . . ? Br2 C19 C20 C21 -179.09(15) . . . . ? C19 C20 C21 C22 -0.4(3) . . . . ? C19 C20 C21 Br1 -179.54(15) . . . . ? C20 C21 C22 C17 -1.0(3) . . . . ? Br1 C21 C22 C17 178.16(14) . . . . ? C18 C17 C22 C21 1.6(3) . . . . ? C11 C17 C22 C21 -178.58(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.64 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.810 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.065 #===END data_19 _database_code_depnum_ccdc_archive 'CCDC 873145' #TrackingRef '- 11-18-19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C22 H18 Br2 O2), C H Cl3' _chemical_formula_sum 'C45 H37 Br4 Cl3 O4' _chemical_formula_weight 1067.74 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0997(12) _cell_length_b 13.8505(18) _cell_length_c 16.388(2) _cell_angle_alpha 90.673(2) _cell_angle_beta 96.255(2) _cell_angle_gamma 96.812(2) _cell_volume 2038.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9947 _cell_measurement_theta_min 2.2681 _cell_measurement_theta_max 30.5250 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 4.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2850 _exptl_absorpt_correction_T_max 0.6793 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _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 SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32715 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 30.55 _reflns_number_total 12390 _reflns_number_gt 10064 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _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^)+(0.0380P)^2^+0.9743P] 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 12390 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Br1A Br 0.10010(3) 0.513602(16) 0.283602(16) 0.03066(6) Uani 1 1 d . . . Br2A Br -0.11923(2) 0.120731(15) 0.207167(12) 0.01858(5) Uani 1 1 d . . . O1A O 0.50867(18) 0.23318(12) 0.19432(10) 0.0257(3) Uani 1 1 d . . . O2A O 0.5901(2) 0.36613(12) 0.27066(11) 0.0326(4) Uani 1 1 d . . . C1A C 0.1846(3) -0.20896(17) 0.44722(15) 0.0263(5) Uani 1 1 d . . . H1A H 0.1717 -0.2722 0.4225 0.032 Uiso 1 1 calc R . . C2A C 0.2585(2) -0.13212(16) 0.40956(14) 0.0228(4) Uani 1 1 d . . . H2A H 0.2946 -0.1434 0.3585 0.027 Uiso 1 1 calc R . . C3A C 0.2820(2) -0.03794(15) 0.44436(12) 0.0178(4) Uani 1 1 d . . . C4A C 0.3657(2) 0.04417(15) 0.40412(12) 0.0168(4) Uani 1 1 d . . . C5A C 0.4237(2) 0.03215(15) 0.33367(13) 0.0200(4) Uani 1 1 d . . . H5A H 0.4032 -0.0298 0.3067 0.024 Uiso 1 1 calc R . . C6A C 0.5185(2) 0.11006(16) 0.29478(14) 0.0207(4) Uani 1 1 d . . . H6A H 0.6197 0.0888 0.2945 0.025 Uiso 1 1 calc R . . C7A C 0.4609(3) 0.13060(16) 0.20582(14) 0.0242(4) Uani 1 1 d . . . H7A H 0.5037 0.0896 0.1669 0.029 Uiso 1 1 calc R . . H7B H 0.3510 0.1171 0.1970 0.029 Uiso 1 1 calc R . . C8A C 0.5506(2) 0.28031(17) 0.26715(14) 0.0237(4) Uani 1 1 d . . . C9A C 0.5377(2) 0.21050(16) 0.33698(13) 0.0209(4) Uani 1 1 d . . . H9A H 0.6341 0.2185 0.3735 0.025 Uiso 1 1 calc R . . C10A C 0.4106(2) 0.22845(15) 0.38919(13) 0.0185(4) Uani 1 1 d . . . H10A H 0.4496 0.2868 0.4250 0.022 Uiso 1 1 calc R . . C11A C 0.3890(2) 0.14310(15) 0.44760(12) 0.0185(4) Uani 1 1 d . . . H11A H 0.4837 0.1453 0.4852 0.022 Uiso 1 1 calc R . . C12A C 0.2663(3) 0.15658(17) 0.50176(13) 0.0239(4) Uani 1 1 d . . . H12A H 0.2898 0.2198 0.5320 0.029 Uiso 1 1 calc R . . H12B H 0.1705 0.1574 0.4669 0.029 Uiso 1 1 calc R . . C13A C 0.2513(3) 0.07491(17) 0.56265(14) 0.0283(5) Uani 1 1 d . . . H13A H 0.3428 0.0793 0.6018 0.034 Uiso 1 1 calc R . . H13B H 0.1665 0.0825 0.5943 0.034 Uiso 1 1 calc R . . C14A C 0.2267(2) -0.02328(16) 0.51988(13) 0.0217(4) Uani 1 1 d . . . C15A C 0.1497(3) -0.10163(18) 0.55615(14) 0.0262(5) Uani 1 1 d . . . H15A H 0.1103 -0.0910 0.6064 0.031 Uiso 1 1 calc R . . C16A C 0.1291(3) -0.19355(18) 0.52142(15) 0.0275(5) Uani 1 1 d . . . H16A H 0.0777 -0.2459 0.5477 0.033 Uiso 1 1 calc R . . C17A C 0.2685(2) 0.25394(15) 0.33998(12) 0.0170(4) Uani 1 1 d . . . C18A C 0.2482(2) 0.35217(15) 0.33469(13) 0.0198(4) Uani 1 1 d . . . H18A H 0.3228 0.4004 0.3599 0.024 Uiso 1 1 calc R . . C19A C 0.1203(2) 0.37942(15) 0.29295(13) 0.0207(4) Uani 1 1 d . . . C20A C 0.0074(2) 0.31238(15) 0.25585(12) 0.0196(4) Uani 1 1 d . . . H20A H -0.0813 0.3321 0.2285 0.024 Uiso 1 1 calc R . . C21A C 0.0293(2) 0.21521(15) 0.26038(12) 0.0162(4) Uani 1 1 d . . . C22A C 0.1571(2) 0.18473(15) 0.30147(12) 0.0166(4) Uani 1 1 d . . . H22A H 0.1687 0.1175 0.3034 0.020 Uiso 1 1 calc R . . Br1B Br 0.16529(3) 0.085916(14) 0.042074(14) 0.02280(5) Uani 1 1 d . . . Br2B Br 0.00426(2) -0.236170(15) 0.234690(12) 0.01968(5) Uani 1 1 d . . . O1B O 0.60058(19) -0.14088(11) 0.23612(10) 0.0270(3) Uani 1 1 d . . . O2B O 0.65343(18) -0.04534(11) 0.13271(11) 0.0288(4) Uani 1 1 d . . . C1B C 0.2091(2) -0.66148(15) 0.09109(14) 0.0218(4) Uani 1 1 d . . . H1B H 0.2049 -0.7120 0.1298 0.026 Uiso 1 1 calc R . . C2B C 0.2992(2) -0.57526(15) 0.11028(13) 0.0193(4) Uani 1 1 d . . . H2B H 0.3555 -0.5670 0.1627 0.023 Uiso 1 1 calc R . . C3B C 0.3101(2) -0.49932(14) 0.05444(12) 0.0150(4) Uani 1 1 d . . . C4B C 0.4062(2) -0.40587(14) 0.07653(12) 0.0147(4) Uani 1 1 d . . . C5B C 0.4842(2) -0.38877(15) 0.15040(13) 0.0182(4) Uani 1 1 d . . . H5B H 0.4716 -0.4367 0.1909 0.022 Uiso 1 1 calc R . . C6B C 0.5902(2) -0.29877(15) 0.17333(13) 0.0193(4) Uani 1 1 d . . . H6B H 0.6921 -0.3192 0.1844 0.023 Uiso 1 1 calc R . . C7B C 0.5597(3) -0.24309(16) 0.25055(14) 0.0264(5) Uani 1 1 d . . . H7C H 0.4531 -0.2556 0.2591 0.032 Uiso 1 1 calc R . . H7D H 0.6201 -0.2637 0.2998 0.032 Uiso 1 1 calc R . . C8B C 0.6221(2) -0.12580(16) 0.15671(14) 0.0223(4) Uani 1 1 d . . . C9B C 0.5971(2) -0.22133(14) 0.10830(13) 0.0187(4) Uani 1 1 d . . . H9B H 0.6858 -0.2271 0.0783 0.022 Uiso 1 1 calc R . . C10B C 0.4571(2) -0.22530(14) 0.04479(12) 0.0158(4) Uani 1 1 d . . . H10B H 0.4878 -0.1851 -0.0022 0.019 Uiso 1 1 calc R . . C11B C 0.4151(2) -0.33007(14) 0.01021(12) 0.0157(4) Uani 1 1 d . . . H11B H 0.4970 -0.3445 -0.0224 0.019 Uiso 1 1 calc R . . C12B C 0.2736(2) -0.33724(15) -0.04959(12) 0.0191(4) Uani 1 1 d . . . H12C H 0.1893 -0.3224 -0.0202 0.023 Uiso 1 1 calc R . . H12D H 0.2864 -0.2890 -0.0931 0.023 Uiso 1 1 calc R . . C13B C 0.2397(3) -0.43872(15) -0.08813(13) 0.0236(4) Uani 1 1 d . . . H13C H 0.1445 -0.4436 -0.1243 0.028 Uiso 1 1 calc R . . H13D H 0.3193 -0.4508 -0.1223 0.028 Uiso 1 1 calc R . . C14B C 0.2289(2) -0.51436(14) -0.02343(13) 0.0181(4) Uani 1 1 d . . . C15B C 0.1359(2) -0.60102(15) -0.04130(14) 0.0231(4) Uani 1 1 d . . . H15B H 0.0788 -0.6101 -0.0935 0.028 Uiso 1 1 calc R . . C16B C 0.1248(2) -0.67433(15) 0.01542(15) 0.0228(4) Uani 1 1 d . . . H16B H 0.0600 -0.7327 0.0024 0.027 Uiso 1 1 calc R . . C17B C 0.3300(2) -0.17884(14) 0.07676(12) 0.0156(4) Uani 1 1 d . . . C18B C 0.3062(2) -0.08626(14) 0.05006(13) 0.0174(4) Uani 1 1 d . . . H18B H 0.3659 -0.0551 0.0117 0.021 Uiso 1 1 calc R . . C19B C 0.1951(2) -0.03953(14) 0.07955(13) 0.0178(4) Uani 1 1 d . . . C20B C 0.1046(2) -0.08199(14) 0.13507(12) 0.0181(4) Uani 1 1 d . . . H20B H 0.0294 -0.0492 0.1552 0.022 Uiso 1 1 calc R . . C21B C 0.1286(2) -0.17439(14) 0.15982(12) 0.0158(4) Uani 1 1 d . . . C22B C 0.2377(2) -0.22392(14) 0.13188(12) 0.0158(4) Uani 1 1 d . . . H22B H 0.2498 -0.2877 0.1499 0.019 Uiso 1 1 calc R . . Cl1 Cl 0.22476(11) 0.54944(7) 0.52687(6) 0.0678(3) Uani 1 1 d . . . Cl2 Cl 0.14316(7) 0.36629(5) 0.60056(5) 0.04277(17) Uani 1 1 d . . . Cl3 Cl 0.45194(7) 0.43635(5) 0.59578(5) 0.04119(16) Uani 1 1 d . . . C23 C 0.2737(3) 0.47061(17) 0.60490(16) 0.0305(5) Uani 1 1 d . . . H23 H 0.2756 0.5048 0.6592 0.037 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 Br1A 0.03897(14) 0.01726(10) 0.03590(13) -0.00083(9) -0.00393(10) 0.01154(9) Br2A 0.01256(9) 0.02256(10) 0.01998(10) 0.00088(7) -0.00055(7) 0.00157(7) O1A 0.0261(8) 0.0254(8) 0.0257(8) 0.0037(6) 0.0059(6) 0.0006(6) O2A 0.0308(9) 0.0263(9) 0.0384(10) 0.0024(7) 0.0037(8) -0.0062(7) C1A 0.0236(11) 0.0244(11) 0.0284(11) 0.0017(9) -0.0050(9) -0.0005(9) C2A 0.0202(10) 0.0244(11) 0.0223(10) -0.0005(8) -0.0010(8) 0.0001(8) C3A 0.0130(9) 0.0221(10) 0.0182(9) 0.0013(8) -0.0024(7) 0.0054(7) C4A 0.0115(8) 0.0195(9) 0.0192(9) 0.0006(7) -0.0030(7) 0.0061(7) C5A 0.0181(9) 0.0195(10) 0.0227(10) -0.0014(8) 0.0019(8) 0.0045(8) C6A 0.0150(9) 0.0216(10) 0.0265(11) -0.0003(8) 0.0048(8) 0.0047(8) C7A 0.0255(11) 0.0219(10) 0.0259(11) -0.0011(8) 0.0070(9) 0.0019(8) C8A 0.0144(9) 0.0274(11) 0.0290(11) 0.0011(9) 0.0027(8) 0.0008(8) C9A 0.0153(9) 0.0233(10) 0.0236(10) 0.0020(8) -0.0009(8) 0.0027(8) C10A 0.0153(9) 0.0187(9) 0.0205(10) -0.0012(8) -0.0024(7) 0.0024(7) C11A 0.0165(9) 0.0208(10) 0.0179(9) -0.0010(7) -0.0033(7) 0.0060(7) C12A 0.0286(11) 0.0260(11) 0.0191(10) 0.0005(8) 0.0029(8) 0.0118(9) C13A 0.0393(13) 0.0302(12) 0.0176(10) 0.0004(9) 0.0040(9) 0.0131(10) C14A 0.0202(10) 0.0271(11) 0.0185(10) 0.0046(8) -0.0031(8) 0.0094(8) C15A 0.0252(11) 0.0364(13) 0.0182(10) 0.0091(9) 0.0006(8) 0.0093(9) C16A 0.0208(11) 0.0325(12) 0.0279(11) 0.0118(10) -0.0032(9) 0.0022(9) C17A 0.0144(9) 0.0200(9) 0.0168(9) 0.0024(7) 0.0009(7) 0.0042(7) C18A 0.0205(10) 0.0165(9) 0.0217(10) -0.0015(8) 0.0004(8) 0.0016(8) C19A 0.0242(10) 0.0170(9) 0.0225(10) 0.0035(8) 0.0041(8) 0.0078(8) C20A 0.0186(9) 0.0228(10) 0.0189(10) 0.0040(8) 0.0009(8) 0.0086(8) C21A 0.0133(8) 0.0207(9) 0.0143(9) 0.0018(7) 0.0014(7) 0.0017(7) C22A 0.0149(9) 0.0167(9) 0.0183(9) 0.0033(7) 0.0011(7) 0.0027(7) Br1B 0.02909(11) 0.01323(9) 0.02674(11) 0.00338(8) 0.00121(9) 0.00663(8) Br2B 0.01771(9) 0.02186(10) 0.01980(10) 0.00035(7) 0.00528(7) 0.00084(7) O1B 0.0312(9) 0.0212(8) 0.0270(8) -0.0062(6) -0.0010(7) 0.0018(7) O2B 0.0265(8) 0.0171(7) 0.0411(10) -0.0041(7) 0.0033(7) -0.0032(6) C1B 0.0267(11) 0.0140(9) 0.0269(11) 0.0030(8) 0.0116(9) 0.0039(8) C2B 0.0235(10) 0.0178(9) 0.0177(9) 0.0023(7) 0.0049(8) 0.0039(8) C3B 0.0153(9) 0.0128(8) 0.0178(9) 0.0006(7) 0.0040(7) 0.0038(7) C4B 0.0140(8) 0.0125(8) 0.0187(9) 0.0013(7) 0.0035(7) 0.0046(7) C5B 0.0166(9) 0.0165(9) 0.0212(10) 0.0016(7) 0.0008(8) 0.0024(7) C6B 0.0164(9) 0.0172(9) 0.0233(10) -0.0011(8) -0.0022(8) 0.0025(7) C7B 0.0299(12) 0.0232(11) 0.0240(11) -0.0011(9) -0.0043(9) 0.0016(9) C8B 0.0151(9) 0.0204(10) 0.0304(11) -0.0050(8) -0.0002(8) 0.0008(8) C9B 0.0143(9) 0.0155(9) 0.0260(10) -0.0030(8) 0.0029(8) 0.0007(7) C10B 0.0158(9) 0.0128(8) 0.0194(9) 0.0013(7) 0.0050(7) 0.0010(7) C11B 0.0174(9) 0.0130(8) 0.0171(9) 0.0012(7) 0.0032(7) 0.0020(7) C12B 0.0241(10) 0.0157(9) 0.0171(9) 0.0028(7) -0.0017(8) 0.0037(8) C13B 0.0339(12) 0.0175(10) 0.0180(10) 0.0007(8) -0.0023(9) 0.0024(9) C14B 0.0204(10) 0.0137(9) 0.0201(10) -0.0005(7) 0.0004(8) 0.0038(7) C15B 0.0247(11) 0.0149(9) 0.0284(11) -0.0044(8) -0.0025(9) 0.0029(8) C16B 0.0190(10) 0.0137(9) 0.0356(12) -0.0028(8) 0.0043(9) 0.0005(7) C17B 0.0156(9) 0.0127(8) 0.0179(9) -0.0011(7) 0.0006(7) 0.0003(7) C18B 0.0177(9) 0.0138(9) 0.0200(9) 0.0001(7) 0.0016(7) 0.0000(7) C19B 0.0208(9) 0.0113(8) 0.0207(10) 0.0011(7) -0.0024(8) 0.0035(7) C20B 0.0176(9) 0.0168(9) 0.0202(10) -0.0029(7) 0.0014(8) 0.0042(7) C21B 0.0149(9) 0.0168(9) 0.0155(9) -0.0002(7) 0.0022(7) 0.0004(7) C22B 0.0161(9) 0.0132(8) 0.0179(9) 0.0011(7) 0.0012(7) 0.0017(7) Cl1 0.0611(5) 0.0697(6) 0.0758(6) 0.0422(5) 0.0036(5) 0.0203(5) Cl2 0.0300(3) 0.0284(3) 0.0717(5) -0.0090(3) 0.0206(3) -0.0020(2) Cl3 0.0264(3) 0.0320(3) 0.0638(5) 0.0068(3) 0.0051(3) -0.0027(2) C23 0.0338(13) 0.0230(11) 0.0339(13) 0.0040(10) 0.0028(10) 0.0010(10) _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 Br1A C19A 1.895(2) . ? Br2A C21A 1.896(2) . ? O1A C8A 1.349(3) . ? O1A C7A 1.456(3) . ? O2A C8A 1.199(3) . ? C1A C2A 1.379(3) . ? C1A C16A 1.390(3) . ? C1A H1A 0.9500 . ? C2A C3A 1.401(3) . ? C2A H2A 0.9500 . ? C3A C14A 1.407(3) . ? C3A C4A 1.493(3) . ? C4A C5A 1.337(3) . ? C4A C11A 1.518(3) . ? C5A C6A 1.494(3) . ? C5A H5A 0.9500 . ? C6A C9A 1.529(3) . ? C6A C7A 1.536(3) . ? C6A H6A 1.0000 . ? C7A H7A 0.9900 . ? C7A H7B 0.9900 . ? C8A C9A 1.512(3) . ? C9A C10A 1.553(3) . ? C9A H9A 1.0000 . ? C10A C17A 1.528(3) . ? C10A C11A 1.538(3) . ? C10A H10A 1.0000 . ? C11A C12A 1.527(3) . ? C11A H11A 1.0000 . ? C12A C13A 1.521(3) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.504(3) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.395(3) . ? C15A C16A 1.372(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C17A C18A 1.397(3) . ? C17A C22A 1.400(3) . ? C18A C19A 1.379(3) . ? C18A H18A 0.9500 . ? C19A C20A 1.383(3) . ? C20A C21A 1.385(3) . ? C20A H20A 0.9500 . ? C21A C22A 1.392(3) . ? C22A H22A 0.9500 . ? Br1B C19B 1.8895(19) . ? Br2B C21B 1.9016(19) . ? O1B C8B 1.352(3) . ? O1B C7B 1.449(3) . ? O2B C8B 1.199(3) . ? C1B C2B 1.378(3) . ? C1B C16B 1.383(3) . ? C1B H1B 0.9500 . ? C2B C3B 1.404(3) . ? C2B H2B 0.9500 . ? C3B C14B 1.403(3) . ? C3B C4B 1.491(3) . ? C4B C5B 1.338(3) . ? C4B C11B 1.522(3) . ? C5B C6B 1.500(3) . ? C5B H5B 0.9500 . ? C6B C9B 1.522(3) . ? C6B C7B 1.542(3) . ? C6B H6B 1.0000 . ? C7B H7C 0.9900 . ? C7B H7D 0.9900 . ? C8B C9B 1.515(3) . ? C9B C10B 1.550(3) . ? C9B H9B 1.0000 . ? C10B C17B 1.525(3) . ? C10B C11B 1.541(3) . ? C10B H10B 1.0000 . ? C11B C12B 1.523(3) . ? C11B H11B 1.0000 . ? C12B C13B 1.518(3) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.502(3) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C15B 1.393(3) . ? C15B C16B 1.387(3) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C17B C18B 1.393(3) . ? C17B C22B 1.402(3) . ? C18B C19B 1.389(3) . ? C18B H18B 0.9500 . ? C19B C20B 1.383(3) . ? C20B C21B 1.382(3) . ? C20B H20B 0.9500 . ? C21B C22B 1.385(3) . ? C22B H22B 0.9500 . ? Cl1 C23 1.746(3) . ? Cl2 C23 1.754(3) . ? Cl3 C23 1.764(3) . ? C23 H23 1.0000 . ? 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 C8A O1A C7A 110.98(17) . . ? C2A C1A C16A 119.8(2) . . ? C2A C1A H1A 120.1 . . ? C16A C1A H1A 120.1 . . ? C1A C2A C3A 122.0(2) . . ? C1A C2A H2A 119.0 . . ? C3A C2A H2A 119.0 . . ? C2A C3A C14A 117.8(2) . . ? C2A C3A C4A 121.53(19) . . ? C14A C3A C4A 120.70(19) . . ? C5A C4A C3A 122.25(19) . . ? C5A C4A C11A 119.98(19) . . ? C3A C4A C11A 117.72(17) . . ? C4A C5A C6A 124.10(19) . . ? C4A C5A H5A 117.9 . . ? C6A C5A H5A 117.9 . . ? C5A C6A C9A 115.83(18) . . ? C5A C6A C7A 114.27(18) . . ? C9A C6A C7A 103.16(17) . . ? C5A C6A H6A 107.7 . . ? C9A C6A H6A 107.7 . . ? C7A C6A H6A 107.7 . . ? O1A C7A C6A 105.77(17) . . ? O1A C7A H7A 110.6 . . ? C6A C7A H7A 110.6 . . ? O1A C7A H7B 110.6 . . ? C6A C7A H7B 110.6 . . ? H7A C7A H7B 108.7 . . ? O2A C8A O1A 121.0(2) . . ? O2A C8A C9A 128.4(2) . . ? O1A C8A C9A 110.53(19) . . ? C8A C9A C6A 103.98(18) . . ? C8A C9A C10A 112.70(17) . . ? C6A C9A C10A 114.27(17) . . ? C8A C9A H9A 108.6 . . ? C6A C9A H9A 108.6 . . ? C10A C9A H9A 108.6 . . ? C17A C10A C11A 115.36(17) . . ? C17A C10A C9A 114.87(17) . . ? C11A C10A C9A 108.15(16) . . ? C17A C10A H10A 105.9 . . ? C11A C10A H10A 105.9 . . ? C9A C10A H10A 105.9 . . ? C4A C11A C12A 112.26(18) . . ? C4A C11A C10A 113.48(17) . . ? C12A C11A C10A 111.00(17) . . ? C4A C11A H11A 106.5 . . ? C12A C11A H11A 106.5 . . ? C10A C11A H11A 106.5 . . ? C13A C12A C11A 110.78(18) . . ? C13A C12A H12A 109.5 . . ? C11A C12A H12A 109.5 . . ? C13A C12A H12B 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 108.1 . . ? C14A C13A C12A 111.49(18) . . ? C14A C13A H13A 109.3 . . ? C12A C13A H13A 109.3 . . ? C14A C13A H13B 109.3 . . ? C12A C13A H13B 109.3 . . ? H13A C13A H13B 108.0 . . ? C15A C14A C3A 119.3(2) . . ? C15A C14A C13A 119.6(2) . . ? C3A C14A C13A 121.1(2) . . ? C16A C15A C14A 122.0(2) . . ? C16A C15A H15A 119.0 . . ? C14A C15A H15A 119.0 . . ? C15A C16A C1A 119.1(2) . . ? C15A C16A H16A 120.5 . . ? C1A C16A H16A 120.5 . . ? C18A C17A C22A 118.47(18) . . ? C18A C17A C10A 117.65(18) . . ? C22A C17A C10A 123.87(18) . . ? C19A C18A C17A 120.25(19) . . ? C19A C18A H18A 119.9 . . ? C17A C18A H18A 119.9 . . ? C18A C19A C20A 122.36(19) . . ? C18A C19A Br1A 119.01(16) . . ? C20A C19A Br1A 118.61(15) . . ? C19A C20A C21A 117.02(18) . . ? C19A C20A H20A 121.5 . . ? C21A C20A H20A 121.5 . . ? C20A C21A C22A 122.39(19) . . ? C20A C21A Br2A 118.64(15) . . ? C22A C21A Br2A 118.96(15) . . ? C21A C22A C17A 119.49(18) . . ? C21A C22A H22A 120.3 . . ? C17A C22A H22A 120.3 . . ? C8B O1B C7B 111.38(16) . . ? C2B C1B C16B 119.9(2) . . ? C2B C1B H1B 120.0 . . ? C16B C1B H1B 120.0 . . ? C1B C2B C3B 121.8(2) . . ? C1B C2B H2B 119.1 . . ? C3B C2B H2B 119.1 . . ? C14B C3B C2B 117.96(18) . . ? C14B C3B C4B 120.81(17) . . ? C2B C3B C4B 121.23(18) . . ? C5B C4B C3B 122.40(18) . . ? C5B C4B C11B 120.68(18) . . ? C3B C4B C11B 116.92(17) . . ? C4B C5B C6B 124.16(19) . . ? C4B C5B H5B 117.9 . . ? C6B C5B H5B 117.9 . . ? C5B C6B C9B 115.58(17) . . ? C5B C6B C7B 115.04(18) . . ? C9B C6B C7B 103.72(17) . . ? C5B C6B H6B 107.3 . . ? C9B C6B H6B 107.3 . . ? C7B C6B H6B 107.3 . . ? O1B C7B C6B 106.22(18) . . ? O1B C7B H7C 110.5 . . ? C6B C7B H7C 110.5 . . ? O1B C7B H7D 110.5 . . ? C6B C7B H7D 110.5 . . ? H7C C7B H7D 108.7 . . ? O2B C8B O1B 121.0(2) . . ? O2B C8B C9B 128.6(2) . . ? O1B C8B C9B 110.40(18) . . ? C8B C9B C6B 104.49(18) . . ? C8B C9B C10B 110.81(16) . . ? C6B C9B C10B 115.20(16) . . ? C8B C9B H9B 108.7 . . ? C6B C9B H9B 108.7 . . ? C10B C9B H9B 108.7 . . ? C17B C10B C11B 115.03(16) . . ? C17B C10B C9B 113.22(16) . . ? C11B C10B C9B 109.44(16) . . ? C17B C10B H10B 106.2 . . ? C11B C10B H10B 106.2 . . ? C9B C10B H10B 106.2 . . ? C4B C11B C12B 112.46(16) . . ? C4B C11B C10B 113.33(16) . . ? C12B C11B C10B 110.66(16) . . ? C4B C11B H11B 106.6 . . ? C12B C11B H11B 106.6 . . ? C10B C11B H11B 106.6 . . ? C13B C12B C11B 110.24(17) . . ? C13B C12B H12C 109.6 . . ? C11B C12B H12C 109.6 . . ? C13B C12B H12D 109.6 . . ? C11B C12B H12D 109.6 . . ? H12C C12B H12D 108.1 . . ? C14B C13B C12B 111.00(17) . . ? C14B C13B H13C 109.4 . . ? C12B C13B H13C 109.4 . . ? C14B C13B H13D 109.4 . . ? C12B C13B H13D 109.4 . . ? H13C C13B H13D 108.0 . . ? C15B C14B C3B 119.52(19) . . ? C15B C14B C13B 119.08(19) . . ? C3B C14B C13B 121.40(18) . . ? C16B C15B C14B 121.5(2) . . ? C16B C15B H15B 119.3 . . ? C14B C15B H15B 119.3 . . ? C1B C16B C15B 119.3(2) . . ? C1B C16B H16B 120.4 . . ? C15B C16B H16B 120.4 . . ? C18B C17B C22B 118.70(18) . . ? C18B C17B C10B 117.81(17) . . ? C22B C17B C10B 123.49(17) . . ? C19B C18B C17B 119.99(19) . . ? C19B C18B H18B 120.0 . . ? C17B C18B H18B 120.0 . . ? C20B C19B C18B 122.24(18) . . ? C20B C19B Br1B 118.75(15) . . ? C18B C19B Br1B 119.01(15) . . ? C21B C20B C19B 116.82(18) . . ? C21B C20B H20B 121.6 . . ? C19B C20B H20B 121.6 . . ? C20B C21B C22B 122.96(18) . . ? C20B C21B Br2B 118.12(15) . . ? C22B C21B Br2B 118.91(15) . . ? C21B C22B C17B 119.27(18) . . ? C21B C22B H22B 120.4 . . ? C17B C22B H22B 120.4 . . ? Cl1 C23 Cl2 110.46(15) . . ? Cl1 C23 Cl3 110.33(14) . . ? Cl2 C23 Cl3 109.42(13) . . ? Cl1 C23 H23 108.9 . . ? Cl2 C23 H23 108.9 . . ? Cl3 C23 H23 108.9 . . ? 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 C16A C1A C2A C3A 1.0(3) . . . . ? C1A C2A C3A C14A -0.3(3) . . . . ? C1A C2A C3A C4A 178.32(19) . . . . ? C2A C3A C4A C5A -0.7(3) . . . . ? C14A C3A C4A C5A 177.91(19) . . . . ? C2A C3A C4A C11A -178.42(18) . . . . ? C14A C3A C4A C11A 0.2(3) . . . . ? C3A C4A C5A C6A -174.82(18) . . . . ? C11A C4A C5A C6A 2.9(3) . . . . ? C4A C5A C6A C9A -4.7(3) . . . . ? C4A C5A C6A C7A -124.4(2) . . . . ? C8A O1A C7A C6A -15.7(2) . . . . ? C5A C6A C7A O1A 149.56(17) . . . . ? C9A C6A C7A O1A 23.0(2) . . . . ? C7A O1A C8A O2A -178.1(2) . . . . ? C7A O1A C8A C9A 1.4(2) . . . . ? O2A C8A C9A C6A -167.0(2) . . . . ? O1A C8A C9A C6A 13.5(2) . . . . ? O2A C8A C9A C10A 68.7(3) . . . . ? O1A C8A C9A C10A -110.8(2) . . . . ? C5A C6A C9A C8A -147.26(18) . . . . ? C7A C6A C9A C8A -21.7(2) . . . . ? C5A C6A C9A C10A -24.0(3) . . . . ? C7A C6A C9A C10A 101.6(2) . . . . ? C8A C9A C10A C17A 39.4(2) . . . . ? C6A C9A C10A C17A -79.0(2) . . . . ? C8A C9A C10A C11A 169.82(17) . . . . ? C6A C9A C10A C11A 51.4(2) . . . . ? C5A C4A C11A C12A 154.67(19) . . . . ? C3A C4A C11A C12A -27.5(2) . . . . ? C5A C4A C11A C10A 27.8(3) . . . . ? C3A C4A C11A C10A -154.42(17) . . . . ? C17A C10A C11A C4A 77.1(2) . . . . ? C9A C10A C11A C4A -53.1(2) . . . . ? C17A C10A C11A C12A -50.5(2) . . . . ? C9A C10A C11A C12A 179.35(17) . . . . ? C4A C11A C12A C13A 55.0(2) . . . . ? C10A C11A C12A C13A -176.83(18) . . . . ? C11A C12A C13A C14A -55.0(3) . . . . ? C2A C3A C14A C15A -0.9(3) . . . . ? C4A C3A C14A C15A -179.59(18) . . . . ? C2A C3A C14A C13A 178.1(2) . . . . ? C4A C3A C14A C13A -0.6(3) . . . . ? C12A C13A C14A C15A -152.7(2) . . . . ? C12A C13A C14A C3A 28.3(3) . . . . ? C3A C14A C15A C16A 1.6(3) . . . . ? C13A C14A C15A C16A -177.4(2) . . . . ? C14A C15A C16A C1A -1.0(3) . . . . ? C2A C1A C16A C15A -0.3(3) . . . . ? C11A C10A C17A C18A 135.3(2) . . . . ? C9A C10A C17A C18A -97.9(2) . . . . ? C11A C10A C17A C22A -43.5(3) . . . . ? C9A C10A C17A C22A 83.3(2) . . . . ? C22A C17A C18A C19A 0.6(3) . . . . ? C10A C17A C18A C19A -178.26(19) . . . . ? C17A C18A C19A C20A 0.8(3) . . . . ? C17A C18A C19A Br1A -177.66(16) . . . . ? C18A C19A C20A C21A -1.6(3) . . . . ? Br1A C19A C20A C21A 176.80(15) . . . . ? C19A C20A C21A C22A 1.2(3) . . . . ? C19A C20A C21A Br2A -177.81(15) . . . . ? C20A C21A C22A C17A 0.0(3) . . . . ? Br2A C21A C22A C17A 179.07(15) . . . . ? C18A C17A C22A C21A -0.9(3) . . . . ? C10A C17A C22A C21A 177.80(18) . . . . ? C16B C1B C2B C3B -0.9(3) . . . . ? C1B C2B C3B C14B -1.7(3) . . . . ? C1B C2B C3B C4B 179.03(18) . . . . ? C14B C3B C4B C5B 179.45(19) . . . . ? C2B C3B C4B C5B -1.3(3) . . . . ? C14B C3B C4B C11B -1.8(3) . . . . ? C2B C3B C4B C11B 177.48(17) . . . . ? C3B C4B C5B C6B 175.63(18) . . . . ? C11B C4B C5B C6B -3.1(3) . . . . ? C4B C5B C6B C9B 4.4(3) . . . . ? C4B C5B C6B C7B 125.3(2) . . . . ? C8B O1B C7B C6B 12.3(2) . . . . ? C5B C6B C7B O1B -145.98(18) . . . . ? C9B C6B C7B O1B -18.8(2) . . . . ? C7B O1B C8B O2B 178.3(2) . . . . ? C7B O1B C8B C9B -0.3(2) . . . . ? O2B C8B C9B C6B 169.6(2) . . . . ? O1B C8B C9B C6B -11.9(2) . . . . ? O2B C8B C9B C10B -65.7(3) . . . . ? O1B C8B C9B C10B 112.77(19) . . . . ? C5B C6B C9B C8B 145.02(18) . . . . ? C7B C6B C9B C8B 18.2(2) . . . . ? C5B C6B C9B C10B 23.2(2) . . . . ? C7B C6B C9B C10B -103.65(19) . . . . ? C8B C9B C10B C17B -38.0(2) . . . . ? C6B C9B C10B C17B 80.3(2) . . . . ? C8B C9B C10B C11B -167.78(17) . . . . ? C6B C9B C10B C11B -49.4(2) . . . . ? C5B C4B C11B C12B -152.09(19) . . . . ? C3B C4B C11B C12B 29.1(2) . . . . ? C5B C4B C11B C10B -25.6(3) . . . . ? C3B C4B C11B C10B 155.57(16) . . . . ? C17B C10B C11B C4B -78.7(2) . . . . ? C9B C10B C11B C4B 50.0(2) . . . . ? C17B C10B C11B C12B 48.7(2) . . . . ? C9B C10B C11B C12B 177.44(16) . . . . ? C4B C11B C12B C13B -56.4(2) . . . . ? C10B C11B C12B C13B 175.74(17) . . . . ? C11B C12B C13B C14B 55.8(2) . . . . ? C2B C3B C14B C15B 3.0(3) . . . . ? C4B C3B C14B C15B -177.69(18) . . . . ? C2B C3B C14B C13B -177.18(19) . . . . ? C4B C3B C14B C13B 2.1(3) . . . . ? C12B C13B C14B C15B 150.3(2) . . . . ? C12B C13B C14B C3B -29.5(3) . . . . ? C3B C14B C15B C16B -1.9(3) . . . . ? C13B C14B C15B C16B 178.3(2) . . . . ? C2B C1B C16B C15B 2.1(3) . . . . ? C14B C15B C16B C1B -0.7(3) . . . . ? C11B C10B C17B C18B -130.43(19) . . . . ? C9B C10B C17B C18B 102.7(2) . . . . ? C11B C10B C17B C22B 50.3(3) . . . . ? C9B C10B C17B C22B -76.6(2) . . . . ? C22B C17B C18B C19B 1.5(3) . . . . ? C10B C17B C18B C19B -177.83(18) . . . . ? C17B C18B C19B C20B -0.4(3) . . . . ? C17B C18B C19B Br1B -179.90(15) . . . . ? C18B C19B C20B C21B -0.5(3) . . . . ? Br1B C19B C20B C21B 178.97(15) . . . . ? C19B C20B C21B C22B 0.3(3) . . . . ? C19B C20B C21B Br2B -178.96(15) . . . . ? C20B C21B C22B C17B 0.8(3) . . . . ? Br2B C21B C22B C17B -179.92(14) . . . . ? C18B C17B C22B C21B -1.7(3) . . . . ? C10B C17B C22B C21B 177.60(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.174 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.088