data_07055 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H18 Br2 O3' _chemical_formula_weight 610.28 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.264(5) _cell_length_b 10.318(6) _cell_length_c 13.601(8) _cell_angle_alpha 84.916(9) _cell_angle_beta 86.667(9) _cell_angle_gamma 67.450(8) _cell_volume 1195.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 9737 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.56 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 3.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5474 _exptl_absorpt_correction_T_max 0.8474 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2005)' _exptl_special_details ; 'Siemens three-circle diffractometer, Bruker APEX CCD' ; _diffrn_ambient_temperature 90(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 CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25422 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 29.57 _reflns_number_total 6689 _reflns_number_gt 5778 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5 (Bruker-AXS, 2003)' _computing_cell_refinement 'SAINT 7 (Bruker-AXS, 2005)' _computing_data_reduction 'SAINT 7 (Bruker-AXS, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0476P)^2^+0.7246P] 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 6689 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 -0.05488(2) 0.81956(2) 0.474870(16) 0.01538(7) Uani 1 1 d . . . Br2 Br -0.01120(2) 0.79605(2) -0.005705(16) 0.01620(7) Uani 1 1 d . . . O1 O 0.63370(17) 0.64134(16) 0.24132(11) 0.0119(3) Uani 1 1 d . . . O2 O 0.61504(18) 0.63850(17) 0.07762(12) 0.0144(3) Uani 1 1 d . . . O3 O 0.58832(18) 0.64592(17) 0.40525(11) 0.0140(3) Uani 1 1 d . . . C1 C 0.3933(2) 0.6397(2) 0.18614(15) 0.0088(4) Uani 1 1 d . . . C2 C 0.3900(2) 0.4970(2) 0.15793(15) 0.0095(4) Uani 1 1 d . . . H2A H 0.3986 0.4889 0.0849 0.011 Uiso 1 1 calc R . . C3 C 0.5272(2) 0.3843(2) 0.21154(15) 0.0101(4) Uani 1 1 d . . . C4 C 0.6577(2) 0.2853(2) 0.16817(16) 0.0125(4) Uani 1 1 d . . . H4A H 0.6674 0.2828 0.0984 0.015 Uiso 1 1 calc R . . C5 C 0.7751(3) 0.1888(2) 0.22826(17) 0.0149(4) Uani 1 1 d . . . H5A H 0.8640 0.1201 0.1991 0.018 Uiso 1 1 calc R . . C6 C 0.7617(3) 0.1936(2) 0.32969(17) 0.0150(4) Uani 1 1 d . . . H6A H 0.8419 0.1281 0.3698 0.018 Uiso 1 1 calc R . . C7 C 0.6315(3) 0.2938(2) 0.37402(16) 0.0132(4) Uani 1 1 d . . . H7A H 0.6230 0.2972 0.4438 0.016 Uiso 1 1 calc R . . C8 C 0.5150(2) 0.3882(2) 0.31444(15) 0.0098(4) Uani 1 1 d . . . C9 C 0.3677(2) 0.5062(2) 0.34969(15) 0.0093(4) Uani 1 1 d . . . H9A H 0.3587 0.5060 0.4233 0.011 Uiso 1 1 calc R . . C10 C 0.3828(2) 0.6444(2) 0.29999(15) 0.0087(4) Uani 1 1 d . . . C11 C 0.2536(2) 0.7875(2) 0.32933(15) 0.0099(4) Uani 1 1 d . . . H11A H 0.2438 0.7947 0.4024 0.012 Uiso 1 1 calc R . . C12 C 0.3029(2) 0.9011(2) 0.27595(16) 0.0109(4) Uani 1 1 d . . . C13 C 0.3438(2) 0.9986(2) 0.31983(17) 0.0140(4) Uani 1 1 d . . . H13A H 0.3384 1.0016 0.3896 0.017 Uiso 1 1 calc R . . C14 C 0.3930(3) 1.0922(2) 0.25969(18) 0.0167(4) Uani 1 1 d . . . H14A H 0.4205 1.1596 0.2889 0.020 Uiso 1 1 calc R . . C15 C 0.4017(3) 1.0873(2) 0.15772(18) 0.0166(4) Uani 1 1 d . . . H15A H 0.4344 1.1518 0.1177 0.020 Uiso 1 1 calc R . . C16 C 0.3628(2) 0.9884(2) 0.11369(17) 0.0127(4) Uani 1 1 d . . . H16A H 0.3708 0.9839 0.0440 0.015 Uiso 1 1 calc R . . C17 C 0.3118(2) 0.8960(2) 0.17320(15) 0.0102(4) Uani 1 1 d . . . C18 C 0.2701(2) 0.7795(2) 0.13801(15) 0.0095(4) Uani 1 1 d . . . H18A H 0.2727 0.7807 0.0643 0.011 Uiso 1 1 calc R . . C19 C 0.5551(2) 0.6401(2) 0.15794(15) 0.0099(4) Uani 1 1 d . . . C20 C 0.5412(2) 0.6443(2) 0.32599(16) 0.0105(4) Uani 1 1 d . . . C21 C 0.2443(2) 0.4795(2) 0.20315(15) 0.0100(4) Uani 1 1 d . . . C22 C 0.1338(2) 0.4525(2) 0.15302(17) 0.0130(4) Uani 1 1 d . . . H22A H 0.1419 0.4486 0.0833 0.016 Uiso 1 1 calc R . . C23 C 0.0102(3) 0.4311(2) 0.20644(18) 0.0159(4) Uani 1 1 d . . . H23A H -0.0665 0.4132 0.1727 0.019 Uiso 1 1 calc R . . C24 C -0.0013(3) 0.4358(2) 0.30837(18) 0.0161(4) Uani 1 1 d . . . H24A H -0.0857 0.4210 0.3439 0.019 Uiso 1 1 calc R . . C25 C 0.1105(2) 0.4621(2) 0.35897(17) 0.0128(4) Uani 1 1 d . . . H25A H 0.1034 0.4643 0.4288 0.015 Uiso 1 1 calc R . . C26 C 0.2326(2) 0.4851(2) 0.30562(16) 0.0105(4) Uani 1 1 d . . . C27 C 0.1007(2) 0.8030(2) 0.28517(16) 0.0104(4) Uani 1 1 d . . . C28 C -0.0404(2) 0.8209(2) 0.33515(16) 0.0108(4) Uani 1 1 d . . . C29 C -0.1727(2) 0.8358(2) 0.28444(17) 0.0139(4) Uani 1 1 d . . . H29A H -0.2687 0.8493 0.3193 0.017 Uiso 1 1 calc R . . C30 C -0.1633(2) 0.8309(2) 0.18278(17) 0.0142(4) Uani 1 1 d . . . H30A H -0.2529 0.8409 0.1475 0.017 Uiso 1 1 calc R . . C31 C -0.0219(2) 0.8112(2) 0.13242(16) 0.0107(4) Uani 1 1 d . . . C32 C 0.1099(2) 0.7980(2) 0.18224(15) 0.0099(4) 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 0.01623(11) 0.01950(12) 0.01136(12) -0.00224(8) 0.00366(8) -0.00817(9) Br2 0.01412(11) 0.02461(13) 0.01157(12) -0.00236(9) -0.00416(8) -0.00849(9) O1 0.0099(6) 0.0172(7) 0.0114(7) -0.0018(6) 0.0004(5) -0.0083(6) O2 0.0125(7) 0.0198(8) 0.0129(7) -0.0024(6) 0.0023(6) -0.0087(6) O3 0.0145(7) 0.0196(8) 0.0108(7) -0.0027(6) -0.0026(6) -0.0091(6) C1 0.0091(8) 0.0132(9) 0.0069(9) -0.0013(7) 0.0005(7) -0.0074(7) C2 0.0107(8) 0.0115(9) 0.0088(9) -0.0025(7) -0.0007(7) -0.0064(7) C3 0.0110(9) 0.0107(9) 0.0119(10) -0.0019(7) 0.0001(7) -0.0077(7) C4 0.0154(9) 0.0127(9) 0.0128(10) -0.0039(8) 0.0026(8) -0.0087(8) C5 0.0127(9) 0.0115(9) 0.0211(11) -0.0029(8) 0.0009(8) -0.0050(8) C6 0.0150(10) 0.0131(10) 0.0176(11) -0.0001(8) -0.0035(8) -0.0058(8) C7 0.0156(9) 0.0133(9) 0.0130(10) -0.0016(8) -0.0027(8) -0.0076(8) C8 0.0100(8) 0.0103(9) 0.0121(10) -0.0017(7) 0.0008(7) -0.0071(7) C9 0.0111(9) 0.0107(9) 0.0086(9) -0.0021(7) 0.0011(7) -0.0066(7) C10 0.0087(8) 0.0109(9) 0.0088(9) -0.0018(7) -0.0003(7) -0.0062(7) C11 0.0099(8) 0.0115(9) 0.0095(9) -0.0036(7) 0.0010(7) -0.0051(7) C12 0.0095(8) 0.0101(9) 0.0138(10) -0.0005(7) -0.0009(7) -0.0048(7) C13 0.0140(9) 0.0117(9) 0.0182(11) -0.0036(8) -0.0018(8) -0.0062(8) C14 0.0169(10) 0.0124(10) 0.0246(12) -0.0042(9) -0.0011(9) -0.0091(8) C15 0.0161(10) 0.0132(10) 0.0229(12) 0.0018(9) -0.0008(8) -0.0089(8) C16 0.0104(9) 0.0129(9) 0.0147(10) 0.0012(8) -0.0004(7) -0.0049(7) C17 0.0086(8) 0.0099(9) 0.0125(10) -0.0003(7) -0.0015(7) -0.0041(7) C18 0.0105(8) 0.0125(9) 0.0080(9) -0.0002(7) -0.0014(7) -0.0070(7) C19 0.0097(8) 0.0102(9) 0.0114(10) -0.0010(7) -0.0009(7) -0.0056(7) C20 0.0110(9) 0.0104(9) 0.0118(10) -0.0020(7) 0.0007(7) -0.0058(7) C21 0.0110(9) 0.0104(9) 0.0109(9) -0.0015(7) -0.0002(7) -0.0065(7) C22 0.0127(9) 0.0119(9) 0.0165(10) -0.0012(8) -0.0036(8) -0.0067(8) C23 0.0130(9) 0.0142(10) 0.0244(12) -0.0035(9) -0.0021(8) -0.0089(8) C24 0.0126(9) 0.0142(10) 0.0243(12) -0.0027(9) 0.0033(8) -0.0086(8) C25 0.0133(9) 0.0118(9) 0.0152(10) -0.0023(8) 0.0026(8) -0.0068(8) C26 0.0113(9) 0.0089(8) 0.0135(10) -0.0019(7) -0.0001(7) -0.0061(7) C27 0.0105(9) 0.0100(9) 0.0125(10) -0.0014(7) -0.0013(7) -0.0058(7) C28 0.0114(9) 0.0092(9) 0.0126(10) -0.0020(7) 0.0019(7) -0.0050(7) C29 0.0107(9) 0.0141(10) 0.0183(11) -0.0017(8) 0.0023(8) -0.0066(8) C30 0.0106(9) 0.0146(10) 0.0197(11) -0.0011(8) -0.0018(8) -0.0072(8) C31 0.0108(9) 0.0103(9) 0.0121(10) -0.0006(7) -0.0015(7) -0.0050(7) C32 0.0105(9) 0.0110(9) 0.0096(9) -0.0018(7) 0.0002(7) -0.0056(7) _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 C28 1.896(2) . ? Br2 C31 1.893(2) . ? O1 C19 1.386(2) . ? O1 C20 1.390(3) . ? O2 C19 1.195(3) . ? O3 C20 1.190(3) . ? C1 C19 1.527(3) . ? C1 C10 1.550(3) . ? C1 C2 1.566(3) . ? C1 C18 1.571(3) . ? C2 C21 1.518(3) . ? C2 C3 1.524(3) . ? C3 C4 1.389(3) . ? C3 C8 1.400(3) . ? C4 C5 1.404(3) . ? C5 C6 1.381(3) . ? C6 C7 1.399(3) . ? C7 C8 1.388(3) . ? C8 C9 1.525(3) . ? C9 C26 1.514(3) . ? C9 C10 1.575(3) . ? C10 C20 1.528(3) . ? C10 C11 1.570(3) . ? C11 C27 1.517(3) . ? C11 C12 1.527(3) . ? C12 C13 1.391(3) . ? C12 C17 1.400(3) . ? C13 C14 1.402(3) . ? C14 C15 1.389(3) . ? C15 C16 1.395(3) . ? C16 C17 1.397(3) . ? C17 C18 1.518(3) . ? C18 C32 1.516(3) . ? C21 C22 1.388(3) . ? C21 C26 1.396(3) . ? C22 C23 1.398(3) . ? C23 C24 1.388(3) . ? C24 C25 1.397(3) . ? C25 C26 1.394(3) . ? C27 C28 1.392(3) . ? C27 C32 1.402(3) . ? C28 C29 1.392(3) . ? C29 C30 1.385(3) . ? C30 C31 1.394(3) . ? C31 C32 1.386(3) . ? 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 C19 O1 C20 110.76(16) . . ? C19 C1 C10 104.06(15) . . ? C19 C1 C2 107.86(16) . . ? C10 C1 C2 109.55(16) . . ? C19 C1 C18 107.15(16) . . ? C10 C1 C18 109.50(16) . . ? C2 C1 C18 117.81(17) . . ? C21 C2 C3 105.81(16) . . ? C21 C2 C1 109.40(16) . . ? C3 C2 C1 104.68(16) . . ? C4 C3 C8 119.79(19) . . ? C4 C3 C2 126.51(19) . . ? C8 C3 C2 113.69(18) . . ? C3 C4 C5 119.5(2) . . ? C6 C5 C4 120.2(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 118.9(2) . . ? C7 C8 C3 120.86(19) . . ? C7 C8 C9 126.01(19) . . ? C3 C8 C9 113.11(18) . . ? C26 C9 C8 105.67(16) . . ? C26 C9 C10 109.47(16) . . ? C8 C9 C10 104.11(16) . . ? C20 C10 C1 103.78(16) . . ? C20 C10 C11 107.73(16) . . ? C1 C10 C11 109.74(16) . . ? C20 C10 C9 108.32(16) . . ? C1 C10 C9 109.94(16) . . ? C11 C10 C9 116.53(16) . . ? C27 C11 C12 106.60(17) . . ? C27 C11 C10 108.44(16) . . ? C12 C11 C10 105.03(16) . . ? C13 C12 C17 120.45(19) . . ? C13 C12 C11 126.5(2) . . ? C17 C12 C11 113.03(17) . . ? C12 C13 C14 119.1(2) . . ? C15 C14 C13 120.5(2) . . ? C14 C15 C16 120.5(2) . . ? C15 C16 C17 119.2(2) . . ? C16 C17 C12 120.23(19) . . ? C16 C17 C18 126.10(19) . . ? C12 C17 C18 113.60(17) . . ? C32 C18 C17 106.85(17) . . ? C32 C18 C1 108.43(16) . . ? C17 C18 C1 104.87(16) . . ? O2 C19 O1 120.87(18) . . ? O2 C19 C1 128.46(19) . . ? O1 C19 C1 110.67(17) . . ? O3 C20 O1 120.79(19) . . ? O3 C20 C10 128.50(19) . . ? O1 C20 C10 110.71(17) . . ? C22 C21 C26 120.49(19) . . ? C22 C21 C2 126.12(19) . . ? C26 C21 C2 113.29(17) . . ? C21 C22 C23 119.2(2) . . ? C24 C23 C22 120.5(2) . . ? C23 C24 C25 120.4(2) . . ? C26 C25 C24 119.1(2) . . ? C25 C26 C21 120.34(19) . . ? C25 C26 C9 125.53(19) . . ? C21 C26 C9 113.96(17) . . ? C28 C27 C32 119.41(18) . . ? C28 C27 C11 127.36(19) . . ? C32 C27 C11 113.23(17) . . ? C29 C28 C27 121.1(2) . . ? C29 C28 Br1 118.33(16) . . ? C27 C28 Br1 120.58(16) . . ? C30 C29 C28 119.44(19) . . ? C29 C30 C31 119.78(19) . . ? C32 C31 C30 121.1(2) . . ? C32 C31 Br2 120.35(16) . . ? C30 C31 Br2 118.49(16) . . ? C31 C32 C27 119.18(19) . . ? C31 C32 C18 127.34(19) . . ? C27 C32 C18 113.48(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.935 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.129