# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name Srinivasa.D.Reddy _publ_contact_author_email 'ds.reddy@ncl.res.in, dsreddy88@yahoo.com' loop_ _publ_author_name 'Pandrangi Swaroop' 'Gajanan Raut' 'Rajesh Gonnade' 'Priyanaka Verma' 'Rajesh Gokhale' Srinivasa.D.Reddy data_8 _database_code_depnum_ccdc_archive 'CCDC 859789' #TrackingRef '- CIFS_8_10_13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N O6' _chemical_formula_sum 'C19 H15 N O6' _chemical_formula_weight 353.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0391(17) _cell_length_b 18.123(3) _cell_length_c 11.275(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.499(9) _cell_angle_gamma 90.00 _cell_volume 1582.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2575 _cell_measurement_theta_min 2.630 _cell_measurement_theta_max 23.775 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9472 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details 'bruker 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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX II' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9119 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2705 _reflns_number_gt 2128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3' _computing_publication_material 'SHELXTL, PLATON' _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^)+(0.0174P)^2^+2.0816P] 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 SHELXL _refine_ls_extinction_coef 0.0016(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2705 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _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 O1 O 0.9264(3) 0.58976(13) 0.1597(2) 0.0348(6) Uani 1 1 d . . . O2 O 0.8758(3) 0.53571(13) 0.3251(2) 0.0358(6) Uani 1 1 d . . . O3 O 0.6072(3) 0.73058(13) 0.1476(2) 0.0373(6) Uani 1 1 d . . . O5 O 0.4637(2) 0.60265(11) -0.16267(19) 0.0222(5) Uani 1 1 d . . . O6 O 1.7430(3) 0.60112(13) 0.6116(2) 0.0372(6) Uani 1 1 d . . . O7 O 1.7509(3) 0.67470(13) 0.4617(2) 0.0383(6) Uani 1 1 d . . . N1 N 1.6754(4) 0.63139(15) 0.5126(3) 0.0278(7) Uani 1 1 d . . . C1 C 0.7501(4) 0.57796(18) 0.0871(3) 0.0282(8) Uani 1 1 d . . . H1 H 0.6715 0.5672 0.1402 0.034 Uiso 1 1 calc R . . C2 C 0.7442(4) 0.51700(17) -0.0070(3) 0.0303(9) Uani 1 1 d . . . H2A H 0.8444 0.4835 0.0207 0.036 Uiso 1 1 calc R . . H2B H 0.6368 0.4877 -0.0196 0.036 Uiso 1 1 calc R . . C3 C 0.7495(4) 0.55632(17) -0.1252(3) 0.0265(8) Uani 1 1 d . . . H3A H 0.8693 0.5691 -0.1247 0.032 Uiso 1 1 calc R . . H3B H 0.6979 0.5255 -0.1982 0.032 Uiso 1 1 calc R . . C4 C 0.6427(4) 0.62501(16) -0.1237(3) 0.0198(7) Uani 1 1 d . . . H4 H 0.6684 0.6641 -0.1788 0.024 Uiso 1 1 calc R . . C6 C 0.3471(4) 0.64953(15) -0.1340(3) 0.0195(7) Uani 1 1 d . . . C7 C 0.1802(4) 0.64963(17) -0.2122(3) 0.0276(8) Uani 1 1 d . . . H7 H 0.1518 0.6195 -0.2837 0.033 Uiso 1 1 calc R . . C8 C 0.0567(4) 0.69425(18) -0.1839(4) 0.0363(10) Uani 1 1 d . . . H8 H -0.0566 0.6956 -0.2377 0.044 Uiso 1 1 calc R . . C9 C 0.0958(5) 0.73734(18) -0.0778(4) 0.0393(10) Uani 1 1 d . . . H9 H 0.0092 0.7671 -0.0586 0.047 Uiso 1 1 calc R . . C10 C 0.2589(5) 0.73669(18) -0.0014(3) 0.0320(9) Uani 1 1 d . . . H10 H 0.2848 0.7658 0.0713 0.038 Uiso 1 1 calc R . . C11 C 0.3887(4) 0.69379(16) -0.0286(3) 0.0221(7) Uani 1 1 d . . . C12 C 0.5657(4) 0.69484(17) 0.0522(3) 0.0248(8) Uani 1 1 d . . . C13 C 0.6968(4) 0.64915(16) 0.0109(3) 0.0227(8) Uani 1 1 d . . . H13 H 0.8029 0.6801 0.0224 0.027 Uiso 1 1 calc R . . C14 C 0.9715(4) 0.56676(16) 0.2767(3) 0.0218(7) Uani 1 1 d . . . C15 C 1.1554(4) 0.58505(16) 0.3368(3) 0.0207(7) Uani 1 1 d . . . C16 C 1.2246(4) 0.56347(16) 0.4589(3) 0.0222(8) Uani 1 1 d . . . H16 H 1.1541 0.5386 0.5017 0.027 Uiso 1 1 calc R . . C17 C 1.3961(4) 0.57832(16) 0.5179(3) 0.0242(8) Uani 1 1 d . . . H17 H 1.4451 0.5639 0.6010 0.029 Uiso 1 1 calc R . . C18 C 1.4928(4) 0.61458(16) 0.4522(3) 0.0233(8) Uani 1 1 d . . . C19 C 1.4278(4) 0.63835(17) 0.3325(3) 0.0261(8) Uani 1 1 d . . . H19 H 1.4979 0.6648 0.2913 0.031 Uiso 1 1 calc R . . C20 C 1.2580(4) 0.62251(17) 0.2747(3) 0.0242(8) Uani 1 1 d . . . H20 H 1.2104 0.6372 0.1916 0.029 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 O1 0.0217(12) 0.0563(16) 0.0238(14) 0.0192(12) 0.0016(10) -0.0065(11) O2 0.0343(14) 0.0509(16) 0.0211(14) 0.0108(12) 0.0055(11) -0.0167(12) O3 0.0555(17) 0.0366(15) 0.0237(14) -0.0097(12) 0.0170(12) -0.0142(12) O5 0.0219(12) 0.0200(12) 0.0246(13) -0.0022(10) 0.0058(10) 0.0037(9) O6 0.0324(14) 0.0361(15) 0.0371(16) 0.0012(13) -0.0013(12) -0.0011(11) O7 0.0353(14) 0.0425(15) 0.0421(16) -0.0041(12) 0.0186(12) -0.0153(12) N1 0.0285(16) 0.0252(16) 0.0309(19) -0.0073(14) 0.0100(14) -0.0016(13) C1 0.0188(17) 0.036(2) 0.028(2) 0.0138(16) 0.0038(15) -0.0047(15) C2 0.0201(17) 0.0207(18) 0.048(2) 0.0122(17) 0.0052(16) 0.0011(14) C3 0.0224(17) 0.0249(18) 0.035(2) 0.0055(15) 0.0124(15) 0.0084(14) C4 0.0169(16) 0.0194(17) 0.0248(19) 0.0057(14) 0.0087(14) 0.0015(13) C6 0.0231(17) 0.0113(15) 0.027(2) 0.0048(14) 0.0110(15) -0.0004(13) C7 0.0244(18) 0.0200(18) 0.036(2) 0.0057(15) 0.0050(16) -0.0037(14) C8 0.0188(18) 0.028(2) 0.063(3) 0.013(2) 0.0129(18) -0.0022(15) C9 0.035(2) 0.021(2) 0.077(3) 0.010(2) 0.040(2) 0.0039(16) C10 0.041(2) 0.0200(18) 0.046(2) 0.0025(16) 0.0306(19) -0.0064(16) C11 0.0303(18) 0.0146(16) 0.028(2) 0.0064(15) 0.0194(15) 0.0006(14) C12 0.036(2) 0.0226(18) 0.019(2) 0.0032(15) 0.0139(16) -0.0073(15) C13 0.0233(17) 0.0213(18) 0.0223(19) 0.0051(14) 0.0037(14) -0.0057(14) C14 0.0302(19) 0.0163(17) 0.0198(19) 0.0026(14) 0.0086(15) 0.0003(14) C15 0.0283(18) 0.0143(16) 0.0203(19) 0.0006(14) 0.0081(15) 0.0020(13) C16 0.0303(19) 0.0173(17) 0.0211(19) 0.0038(14) 0.0107(15) -0.0024(14) C17 0.0313(19) 0.0208(18) 0.0189(18) 0.0014(14) 0.0043(15) -0.0024(14) C18 0.0232(17) 0.0173(17) 0.031(2) -0.0066(15) 0.0101(15) -0.0007(14) C19 0.034(2) 0.0217(18) 0.028(2) -0.0023(15) 0.0169(16) -0.0038(15) C20 0.037(2) 0.0228(18) 0.0154(18) 0.0012(14) 0.0116(15) -0.0022(15) _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 O1 C14 1.338(4) . ? O1 C1 1.451(4) . ? O2 C14 1.196(4) . ? O3 C12 1.223(4) . ? O5 C6 1.366(3) . ? O5 C4 1.446(3) . ? O6 N1 1.232(3) . ? O7 N1 1.225(3) . ? N1 C18 1.476(4) . ? C1 C2 1.524(5) . ? C1 C13 1.545(4) . ? C1 H1 1.0000 . ? C2 C3 1.521(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C13 1.527(4) . ? C4 H4 1.0000 . ? C6 C7 1.395(4) . ? C6 C11 1.398(4) . ? C7 C8 1.382(5) . ? C7 H7 0.9500 . ? C8 C9 1.393(5) . ? C8 H8 0.9500 . ? C9 C10 1.362(5) . ? C9 H9 0.9500 . ? C10 C11 1.399(4) . ? C10 H10 0.9500 . ? C11 C12 1.471(5) . ? C12 C13 1.508(4) . ? C13 H13 1.0000 . ? C14 C15 1.490(4) . ? C15 C20 1.394(4) . ? C15 C16 1.395(4) . ? C16 C17 1.388(4) . ? C16 H16 0.9500 . ? C17 C18 1.376(4) . ? C17 H17 0.9500 . ? C18 C19 1.379(4) . ? C19 C20 1.376(4) . ? C19 H19 0.9500 . ? C20 H20 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 C14 O1 C1 118.5(2) . . ? C6 O5 C4 116.3(2) . . ? O7 N1 O6 123.8(3) . . ? O7 N1 C18 118.2(3) . . ? O6 N1 C18 118.1(3) . . ? O1 C1 C2 110.1(3) . . ? O1 C1 C13 105.9(2) . . ? C2 C1 C13 105.4(3) . . ? O1 C1 H1 111.7 . . ? C2 C1 H1 111.7 . . ? C13 C1 H1 111.7 . . ? C3 C2 C1 105.5(3) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 103.1(3) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? O5 C4 C3 106.7(2) . . ? O5 C4 C13 112.2(2) . . ? C3 C4 C13 103.6(2) . . ? O5 C4 H4 111.3 . . ? C3 C4 H4 111.3 . . ? C13 C4 H4 111.3 . . ? O5 C6 C7 117.1(3) . . ? O5 C6 C11 122.3(3) . . ? C7 C6 C11 120.5(3) . . ? C8 C7 C6 118.9(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C9 121.0(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 121.0(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C6 C11 C10 118.8(3) . . ? C6 C11 C12 120.4(3) . . ? C10 C11 C12 120.8(3) . . ? O3 C12 C11 122.9(3) . . ? O3 C12 C13 120.9(3) . . ? C11 C12 C13 116.2(3) . . ? C12 C13 C4 115.3(3) . . ? C12 C13 C1 113.6(3) . . ? C4 C13 C1 106.0(2) . . ? C12 C13 H13 107.2 . . ? C4 C13 H13 107.2 . . ? C1 C13 H13 107.2 . . ? O2 C14 O1 124.0(3) . . ? O2 C14 C15 125.3(3) . . ? O1 C14 C15 110.7(3) . . ? C20 C15 C16 119.9(3) . . ? C20 C15 C14 121.9(3) . . ? C16 C15 C14 118.2(3) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 117.8(3) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.1 . . ? C17 C18 C19 123.7(3) . . ? C17 C18 N1 119.0(3) . . ? C19 C18 N1 117.2(3) . . ? C20 C19 C18 117.8(3) . . ? C20 C19 H19 121.1 . . ? C18 C19 H19 121.1 . . ? C19 C20 C15 120.6(3) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? 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 C14 O1 C1 C2 -107.4(3) . . . . ? C14 O1 C1 C13 139.1(3) . . . . ? O1 C1 C2 C3 -95.2(3) . . . . ? C13 C1 C2 C3 18.7(3) . . . . ? C1 C2 C3 C4 -36.8(3) . . . . ? C6 O5 C4 C3 161.2(2) . . . . ? C6 O5 C4 C13 48.4(3) . . . . ? C2 C3 C4 O5 -78.3(3) . . . . ? C2 C3 C4 C13 40.3(3) . . . . ? C4 O5 C6 C7 151.5(3) . . . . ? C4 O5 C6 C11 -31.1(4) . . . . ? O5 C6 C7 C8 177.6(3) . . . . ? C11 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 -1.5(5) . . . . ? C7 C8 C9 C10 1.2(5) . . . . ? C8 C9 C10 C11 0.6(5) . . . . ? O5 C6 C11 C10 -175.8(3) . . . . ? C7 C6 C11 C10 1.6(4) . . . . ? O5 C6 C11 C12 4.0(4) . . . . ? C7 C6 C11 C12 -178.6(3) . . . . ? C9 C10 C11 C6 -1.9(5) . . . . ? C9 C10 C11 C12 178.3(3) . . . . ? C6 C11 C12 O3 -177.4(3) . . . . ? C10 C11 C12 O3 2.4(5) . . . . ? C6 C11 C12 C13 2.9(4) . . . . ? C10 C11 C12 C13 -177.3(3) . . . . ? O3 C12 C13 C4 -163.7(3) . . . . ? C11 C12 C13 C4 16.0(4) . . . . ? O3 C12 C13 C1 73.7(4) . . . . ? C11 C12 C13 C1 -106.6(3) . . . . ? O5 C4 C13 C12 -40.7(3) . . . . ? C3 C4 C13 C12 -155.4(3) . . . . ? O5 C4 C13 C1 85.9(3) . . . . ? C3 C4 C13 C1 -28.8(3) . . . . ? O1 C1 C13 C12 -109.4(3) . . . . ? C2 C1 C13 C12 133.8(3) . . . . ? O1 C1 C13 C4 123.0(3) . . . . ? C2 C1 C13 C4 6.2(3) . . . . ? C1 O1 C14 O2 1.3(5) . . . . ? C1 O1 C14 C15 -178.8(3) . . . . ? O2 C14 C15 C20 -178.9(3) . . . . ? O1 C14 C15 C20 1.2(4) . . . . ? O2 C14 C15 C16 1.2(5) . . . . ? O1 C14 C15 C16 -178.7(3) . . . . ? C20 C15 C16 C17 -0.9(4) . . . . ? C14 C15 C16 C17 179.0(3) . . . . ? C15 C16 C17 C18 0.1(4) . . . . ? C16 C17 C18 C19 1.6(5) . . . . ? C16 C17 C18 N1 179.8(3) . . . . ? O7 N1 C18 C17 -167.1(3) . . . . ? O6 N1 C18 C17 12.8(4) . . . . ? O7 N1 C18 C19 11.2(4) . . . . ? O6 N1 C18 C19 -169.0(3) . . . . ? C17 C18 C19 C20 -2.3(5) . . . . ? N1 C18 C19 C20 179.5(3) . . . . ? C18 C19 C20 C15 1.4(5) . . . . ? C16 C15 C20 C19 0.2(5) . . . . ? C14 C15 C20 C19 -179.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.225 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.053 #===END data_10 _database_code_depnum_ccdc_archive 'CCDC 859790' #TrackingRef '- CIFS_8_10_13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Br2 O4' _chemical_formula_sum 'C12 H10 Br2 O4' _chemical_formula_weight 378.02 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 7.6833(5) _cell_length_b 12.1129(8) _cell_length_c 13.7371(9) _cell_angle_alpha 97.440(3) _cell_angle_beta 97.440(3) _cell_angle_gamma 102.311(3) _cell_volume 1222.16(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9925 _cell_measurement_theta_min 2.489 _cell_measurement_theta_max 28.645 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 6.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1186 _exptl_absorpt_correction_T_max 0.6538 _exptl_absorpt_process_details 'bruker 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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX II' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20413 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5313 _reflns_number_gt 4563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3' _computing_publication_material 'SHELXTL, PLATON' _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^)+(0.0221P)^2^+0.8800P] 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 5313 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.002 _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 0.72769(4) -0.09912(2) 0.56826(2) 0.03091(7) Uani 1 1 d . . . Br2A Br 1.15749(3) 0.103950(19) 0.941439(17) 0.02099(6) Uani 1 1 d . . . O1A O 1.1991(2) 0.41467(15) 0.50502(12) 0.0256(4) Uani 1 1 d . . . H1A H 1.2757 0.4138 0.5543 0.038 Uiso 1 1 calc R . . O2A O 1.1151(2) 0.31997(12) 0.86441(11) 0.0190(3) Uani 1 1 d . . . H2A H 1.0970 0.3794 0.8435 0.029 Uiso 1 1 calc R . . O3A O 1.0329(2) 0.44041(13) 0.72997(11) 0.0196(3) Uani 1 1 d . . . O5A O 0.7672(2) 0.14414(13) 0.54244(12) 0.0239(4) Uani 1 1 d . . . C1A C 1.0457(3) 0.3221(2) 0.49815(16) 0.0205(5) Uani 1 1 d . . . H1A1 H 1.0861 0.2529 0.5157 0.025 Uiso 1 1 calc R . . C2A C 0.9352(3) 0.2940(2) 0.39318(17) 0.0263(6) Uani 1 1 d . . . H2A2 H 0.9772 0.2355 0.3511 0.032 Uiso 1 1 calc R . . H2A1 H 0.9462 0.3635 0.3615 0.032 Uiso 1 1 calc R . . C3A C 0.7375(3) 0.2477(2) 0.40693(18) 0.0280(6) Uani 1 1 d . . . H3A1 H 0.6590 0.2953 0.3798 0.034 Uiso 1 1 calc R . . H3A2 H 0.6915 0.1678 0.3723 0.034 Uiso 1 1 calc R . . C4A C 0.7410(3) 0.2537(2) 0.51865(17) 0.0232(5) Uani 1 1 d . . . H4A H 0.6282 0.2709 0.5393 0.028 Uiso 1 1 calc R . . C6A C 0.8528(3) 0.14013(19) 0.63348(17) 0.0184(5) Uani 1 1 d . . . C7A C 0.8535(3) 0.03262(19) 0.65870(17) 0.0203(5) Uani 1 1 d . . . C8A C 0.9457(3) 0.02282(19) 0.74950(18) 0.0207(5) Uani 1 1 d . . . H8A H 0.9490 -0.0510 0.7649 0.025 Uiso 1 1 calc R . . C9A C 1.0329(3) 0.11892(19) 0.81819(16) 0.0179(5) Uani 1 1 d . . . C10A C 1.0300(3) 0.22733(19) 0.79658(17) 0.0168(5) Uani 1 1 d . . . C11A C 0.9435(3) 0.23841(18) 0.70263(16) 0.0158(5) Uani 1 1 d . . . C12A C 0.9640(3) 0.35037(19) 0.67158(16) 0.0168(5) Uani 1 1 d . . . C13A C 0.9067(3) 0.34921(19) 0.56335(17) 0.0191(5) Uani 1 1 d . . . H13A H 0.8808 0.4248 0.5532 0.023 Uiso 1 1 calc R . . Br1B Br 0.14372(3) 0.64796(2) -0.089315(17) 0.02315(7) Uani 1 1 d . . . Br2B Br 0.45993(3) 1.071271(19) 0.160324(17) 0.02273(6) Uani 1 1 d . . . O1B O 0.4470(2) 0.48370(15) 0.38231(12) 0.0266(4) Uani 1 1 d . . . H1B H 0.3639 0.4562 0.4126 0.040 Uiso 1 1 calc R . . O2B O 0.5922(2) 0.91792(13) 0.29405(11) 0.0211(4) Uani 1 1 d . . . H2B H 0.6291 0.8746 0.3308 0.032 Uiso 1 1 calc R . . O3B O 0.6368(2) 0.72240(13) 0.34279(11) 0.0220(4) Uani 1 1 d . . . O5B O 0.3247(2) 0.55682(12) 0.07916(11) 0.0177(3) Uani 1 1 d . . . C1B C 0.3771(3) 0.47469(19) 0.28062(16) 0.0193(5) Uani 1 1 d . . . H1B1 H 0.2640 0.5033 0.2731 0.023 Uiso 1 1 calc R . . C2B C 0.3457(4) 0.3557(2) 0.21905(18) 0.0244(5) Uani 1 1 d . . . H2B1 H 0.2219 0.3107 0.2189 0.029 Uiso 1 1 calc R . . H2B2 H 0.4331 0.3137 0.2465 0.029 Uiso 1 1 calc R . . C3B C 0.3729(3) 0.37582(19) 0.11305(17) 0.0199(5) Uani 1 1 d . . . H3B1 H 0.4505 0.3276 0.0864 0.024 Uiso 1 1 calc R . . H3B2 H 0.2553 0.3567 0.0681 0.024 Uiso 1 1 calc R . . C4B C 0.4634(3) 0.50287(18) 0.12133(16) 0.0172(5) Uani 1 1 d . . . H4B H 0.5690 0.5137 0.0850 0.021 Uiso 1 1 calc R . . C6B C 0.3597(3) 0.67248(18) 0.10061(16) 0.0154(5) Uani 1 1 d . . . C7B C 0.2815(3) 0.73025(19) 0.03264(16) 0.0164(5) Uani 1 1 d . . . C8B C 0.3100(3) 0.84829(19) 0.05169(16) 0.0181(5) Uani 1 1 d . . . H8B H 0.2571 0.8872 0.0043 0.022 Uiso 1 1 calc R . . C9B C 0.4145(3) 0.90990(18) 0.13893(17) 0.0176(5) Uani 1 1 d . . . C10B C 0.4929(3) 0.85504(19) 0.21007(16) 0.0165(5) Uani 1 1 d . . . C11B C 0.4657(3) 0.73481(18) 0.19029(16) 0.0156(5) Uani 1 1 d . . . C12B C 0.5481(3) 0.67332(19) 0.26079(16) 0.0161(5) Uani 1 1 d . . . C13B C 0.5219(3) 0.54652(18) 0.23182(16) 0.0157(5) Uani 1 1 d . . . H13B H 0.6394 0.5264 0.2526 0.019 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 0.03187(15) 0.02022(12) 0.03307(15) -0.00916(10) -0.00558(12) 0.00415(11) Br2A 0.02281(13) 0.02179(12) 0.01883(12) 0.00631(9) 0.00291(10) 0.00469(10) O1A 0.0194(9) 0.0382(10) 0.0187(9) 0.0090(7) -0.0006(7) 0.0052(8) O2A 0.0236(9) 0.0161(8) 0.0148(8) 0.0001(6) 0.0005(7) 0.0020(7) O3A 0.0192(9) 0.0182(8) 0.0196(8) -0.0004(6) 0.0009(7) 0.0041(7) O5A 0.0242(9) 0.0238(9) 0.0187(8) -0.0027(7) -0.0054(7) 0.0038(7) C1A 0.0221(13) 0.0262(12) 0.0141(11) 0.0040(9) 0.0019(10) 0.0081(10) C2A 0.0322(15) 0.0324(13) 0.0150(12) 0.0031(10) -0.0001(11) 0.0116(12) C3A 0.0264(14) 0.0343(14) 0.0205(13) 0.0013(10) -0.0065(11) 0.0092(12) C4A 0.0223(13) 0.0260(12) 0.0204(12) -0.0001(10) -0.0021(10) 0.0094(11) C6A 0.0130(11) 0.0244(12) 0.0165(11) -0.0015(9) 0.0017(9) 0.0047(9) C7A 0.0183(12) 0.0168(11) 0.0214(12) -0.0062(9) 0.0017(10) 0.0010(9) C8A 0.0183(12) 0.0178(11) 0.0265(13) 0.0011(9) 0.0071(10) 0.0050(10) C9A 0.0140(12) 0.0237(12) 0.0167(11) 0.0040(9) 0.0034(9) 0.0052(10) C10A 0.0126(11) 0.0191(11) 0.0173(11) -0.0014(9) 0.0059(9) 0.0013(9) C11A 0.0122(11) 0.0176(11) 0.0162(11) -0.0009(8) 0.0024(9) 0.0024(9) C12A 0.0105(11) 0.0234(11) 0.0174(11) 0.0012(9) 0.0023(9) 0.0069(9) C13A 0.0182(12) 0.0220(11) 0.0173(11) 0.0017(9) -0.0008(10) 0.0081(10) Br1B 0.02144(13) 0.02687(13) 0.01774(12) -0.00393(9) -0.00671(10) 0.00866(10) Br2B 0.02865(14) 0.01775(11) 0.02040(12) 0.00141(9) 0.00199(10) 0.00455(10) O1B 0.0249(10) 0.0362(10) 0.0155(8) 0.0062(7) 0.0030(7) -0.0009(8) O2B 0.0255(9) 0.0199(8) 0.0144(8) -0.0008(6) -0.0009(7) 0.0025(7) O3B 0.0237(9) 0.0237(8) 0.0148(8) -0.0007(6) -0.0018(7) 0.0029(7) O5B 0.0166(8) 0.0174(8) 0.0169(8) -0.0013(6) -0.0024(7) 0.0048(6) C1B 0.0179(12) 0.0255(12) 0.0151(11) 0.0037(9) 0.0013(9) 0.0069(10) C2B 0.0290(14) 0.0199(11) 0.0227(12) 0.0053(9) -0.0006(11) 0.0039(10) C3B 0.0188(12) 0.0198(11) 0.0200(12) -0.0005(9) 0.0019(10) 0.0049(10) C4B 0.0139(11) 0.0213(11) 0.0167(11) 0.0016(9) 0.0021(9) 0.0057(9) C6B 0.0110(11) 0.0194(11) 0.0152(11) -0.0001(8) 0.0046(9) 0.0024(9) C7B 0.0130(11) 0.0223(11) 0.0122(11) -0.0016(8) 0.0012(9) 0.0035(9) C8B 0.0150(12) 0.0236(12) 0.0168(11) 0.0019(9) 0.0025(9) 0.0079(10) C9B 0.0161(12) 0.0174(11) 0.0201(12) 0.0009(9) 0.0055(10) 0.0054(9) C10B 0.0115(11) 0.0230(11) 0.0132(11) -0.0005(9) 0.0035(9) 0.0013(9) C11B 0.0135(11) 0.0201(11) 0.0128(11) 0.0007(8) 0.0034(9) 0.0039(9) C12B 0.0118(11) 0.0230(11) 0.0128(11) 0.0014(9) 0.0046(9) 0.0018(9) C13B 0.0137(11) 0.0181(11) 0.0158(11) 0.0022(8) 0.0033(9) 0.0045(9) _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 C7A 1.882(2) . ? Br2A C9A 1.884(2) . ? O1A C1A 1.427(3) . ? O1A H1A 0.8400 . ? O2A C10A 1.347(3) . ? O2A H2A 0.8400 . ? O3A C12A 1.237(3) . ? O5A C6A 1.347(3) . ? O5A C4A 1.455(3) . ? C1A C2A 1.533(3) . ? C1A C13A 1.541(3) . ? C1A H1A1 1.0000 . ? C2A C3A 1.548(4) . ? C2A H2A2 0.9900 . ? C2A H2A1 0.9900 . ? C3A C4A 1.524(3) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C13A 1.524(3) . ? C4A H4A 1.0000 . ? C6A C7A 1.391(3) . ? C6A C11A 1.410(3) . ? C7A C8A 1.384(3) . ? C8A C9A 1.383(3) . ? C8A H8A 0.9500 . ? C9A C10A 1.387(3) . ? C10A C11A 1.409(3) . ? C11A C12A 1.457(3) . ? C12A C13A 1.492(3) . ? C13A H13A 1.0000 . ? Br1B C7B 1.892(2) . ? Br2B C9B 1.887(2) . ? O1B C1B 1.412(3) . ? O1B H1B 0.8400 . ? O2B C10B 1.338(3) . ? O2B H2B 0.8400 . ? O3B C12B 1.242(3) . ? O5B C6B 1.354(3) . ? O5B C4B 1.461(3) . ? C1B C2B 1.528(3) . ? C1B C13B 1.541(3) . ? C1B H1B1 1.0000 . ? C2B C3B 1.540(3) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.531(3) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B C13B 1.516(3) . ? C4B H4B 1.0000 . ? C6B C7B 1.387(3) . ? C6B C11B 1.410(3) . ? C7B C8B 1.384(3) . ? C8B C9B 1.379(3) . ? C8B H8B 0.9500 . ? C9B C10B 1.395(3) . ? C10B C11B 1.411(3) . ? C11B C12B 1.457(3) . ? C12B C13B 1.499(3) . ? C13B H13B 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 C1A O1A H1A 109.5 . . ? C10A O2A H2A 109.5 . . ? C6A O5A C4A 118.99(17) . . ? O1A C1A C2A 111.07(19) . . ? O1A C1A C13A 113.91(19) . . ? C2A C1A C13A 102.58(19) . . ? O1A C1A H1A1 109.7 . . ? C2A C1A H1A1 109.7 . . ? C13A C1A H1A1 109.7 . . ? C1A C2A C3A 105.6(2) . . ? C1A C2A H2A2 110.6 . . ? C3A C2A H2A2 110.6 . . ? C1A C2A H2A1 110.6 . . ? C3A C2A H2A1 110.6 . . ? H2A2 C2A H2A1 108.8 . . ? C4A C3A C2A 105.90(19) . . ? C4A C3A H3A1 110.6 . . ? C2A C3A H3A1 110.6 . . ? C4A C3A H3A2 110.6 . . ? C2A C3A H3A2 110.6 . . ? H3A1 C3A H3A2 108.7 . . ? O5A C4A C13A 110.63(18) . . ? O5A C4A C3A 106.64(19) . . ? C13A C4A C3A 103.5(2) . . ? O5A C4A H4A 111.9 . . ? C13A C4A H4A 111.9 . . ? C3A C4A H4A 111.9 . . ? O5A C6A C7A 117.5(2) . . ? O5A C6A C11A 123.5(2) . . ? C7A C6A C11A 119.0(2) . . ? C8A C7A C6A 120.3(2) . . ? C8A C7A Br1A 120.43(17) . . ? C6A C7A Br1A 119.31(17) . . ? C9A C8A C7A 121.0(2) . . ? C9A C8A H8A 119.5 . . ? C7A C8A H8A 119.5 . . ? C8A C9A C10A 120.2(2) . . ? C8A C9A Br2A 120.42(17) . . ? C10A C9A Br2A 119.43(17) . . ? O2A C10A C9A 119.4(2) . . ? O2A C10A C11A 121.3(2) . . ? C9A C10A C11A 119.3(2) . . ? C10A C11A C6A 120.2(2) . . ? C10A C11A C12A 120.41(19) . . ? C6A C11A C12A 119.0(2) . . ? O3A C12A C11A 122.3(2) . . ? O3A C12A C13A 122.0(2) . . ? C11A C12A C13A 115.62(19) . . ? C12A C13A C4A 112.6(2) . . ? C12A C13A C1A 113.79(18) . . ? C4A C13A C1A 101.77(18) . . ? C12A C13A H13A 109.5 . . ? C4A C13A H13A 109.5 . . ? C1A C13A H13A 109.5 . . ? C1B O1B H1B 109.5 . . ? C10B O2B H2B 109.5 . . ? C6B O5B C4B 116.44(16) . . ? O1B C1B C2B 115.31(18) . . ? O1B C1B C13B 107.99(18) . . ? C2B C1B C13B 102.20(19) . . ? O1B C1B H1B1 110.3 . . ? C2B C1B H1B1 110.3 . . ? C13B C1B H1B1 110.3 . . ? C1B C2B C3B 105.73(18) . . ? C1B C2B H2B1 110.6 . . ? C3B C2B H2B1 110.6 . . ? C1B C2B H2B2 110.6 . . ? C3B C2B H2B2 110.6 . . ? H2B1 C2B H2B2 108.7 . . ? C4B C3B C2B 106.39(18) . . ? C4B C3B H3B1 110.5 . . ? C2B C3B H3B1 110.5 . . ? C4B C3B H3B2 110.5 . . ? C2B C3B H3B2 110.5 . . ? H3B1 C3B H3B2 108.6 . . ? O5B C4B C13B 111.20(17) . . ? O5B C4B C3B 106.23(17) . . ? C13B C4B C3B 105.48(18) . . ? O5B C4B H4B 111.2 . . ? C13B C4B H4B 111.2 . . ? C3B C4B H4B 111.2 . . ? O5B C6B C7B 117.98(19) . . ? O5B C6B C11B 122.52(19) . . ? C7B C6B C11B 119.5(2) . . ? C8B C7B C6B 120.4(2) . . ? C8B C7B Br1B 119.73(16) . . ? C6B C7B Br1B 119.83(16) . . ? C9B C8B C7B 120.5(2) . . ? C9B C8B H8B 119.8 . . ? C7B C8B H8B 119.8 . . ? C8B C9B C10B 121.0(2) . . ? C8B C9B Br2B 119.56(17) . . ? C10B C9B Br2B 119.40(16) . . ? O2B C10B C9B 119.1(2) . . ? O2B C10B C11B 122.3(2) . . ? C9B C10B C11B 118.61(19) . . ? C6B C11B C10B 120.1(2) . . ? C6B C11B C12B 118.97(19) . . ? C10B C11B C12B 120.96(19) . . ? O3B C12B C11B 122.2(2) . . ? O3B C12B C13B 120.0(2) . . ? C11B C12B C13B 117.80(18) . . ? C12B C13B C4B 114.56(18) . . ? C12B C13B C1B 114.00(19) . . ? C4B C13B C1B 104.14(18) . . ? C12B C13B H13B 107.9 . . ? C4B C13B H13B 107.9 . . ? C1B C13B H13B 107.9 . . ? 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 O1A C1A C2A C3A -149.71(19) . . . . ? C13A C1A C2A C3A -27.6(2) . . . . ? C1A C2A C3A C4A 1.4(3) . . . . ? C6A O5A C4A C13A 38.9(3) . . . . ? C6A O5A C4A C3A 150.8(2) . . . . ? C2A C3A C4A O5A -90.9(2) . . . . ? C2A C3A C4A C13A 25.9(2) . . . . ? C4A O5A C6A C7A 171.2(2) . . . . ? C4A O5A C6A C11A -10.1(3) . . . . ? O5A C6A C7A C8A 177.3(2) . . . . ? C11A C6A C7A C8A -1.4(4) . . . . ? O5A C6A C7A Br1A -2.9(3) . . . . ? C11A C6A C7A Br1A 178.42(17) . . . . ? C6A C7A C8A C9A 2.3(4) . . . . ? Br1A C7A C8A C9A -177.51(18) . . . . ? C7A C8A C9A C10A -0.3(4) . . . . ? C7A C8A C9A Br2A 179.96(18) . . . . ? C8A C9A C10A O2A 179.8(2) . . . . ? Br2A C9A C10A O2A -0.5(3) . . . . ? C8A C9A C10A C11A -2.5(3) . . . . ? Br2A C9A C10A C11A 177.21(17) . . . . ? O2A C10A C11A C6A -179.0(2) . . . . ? C9A C10A C11A C6A 3.4(3) . . . . ? O2A C10A C11A C12A 8.0(3) . . . . ? C9A C10A C11A C12A -169.6(2) . . . . ? O5A C6A C11A C10A 180.0(2) . . . . ? C7A C6A C11A C10A -1.4(3) . . . . ? O5A C6A C11A C12A -6.9(3) . . . . ? C7A C6A C11A C12A 171.7(2) . . . . ? C10A C11A C12A O3A -11.1(3) . . . . ? C6A C11A C12A O3A 175.8(2) . . . . ? C10A C11A C12A C13A 165.3(2) . . . . ? C6A C11A C12A C13A -7.8(3) . . . . ? O3A C12A C13A C4A -146.9(2) . . . . ? C11A C12A C13A C4A 36.6(3) . . . . ? O3A C12A C13A C1A 97.9(3) . . . . ? C11A C12A C13A C1A -78.5(3) . . . . ? O5A C4A C13A C12A -51.4(3) . . . . ? C3A C4A C13A C12A -165.27(19) . . . . ? O5A C4A C13A C1A 70.8(2) . . . . ? C3A C4A C13A C1A -43.1(2) . . . . ? O1A C1A C13A C12A -74.8(2) . . . . ? C2A C1A C13A C12A 165.05(19) . . . . ? O1A C1A C13A C4A 163.79(18) . . . . ? C2A C1A C13A C4A 43.7(2) . . . . ? O1B C1B C2B C3B -149.8(2) . . . . ? C13B C1B C2B C3B -33.0(2) . . . . ? C1B C2B C3B C4B 13.6(2) . . . . ? C6B O5B C4B C13B 49.7(3) . . . . ? C6B O5B C4B C3B 163.96(18) . . . . ? C2B C3B C4B O5B -106.4(2) . . . . ? C2B C3B C4B C13B 11.7(2) . . . . ? C4B O5B C6B C7B 152.0(2) . . . . ? C4B O5B C6B C11B -30.5(3) . . . . ? O5B C6B C7B C8B 178.8(2) . . . . ? C11B C6B C7B C8B 1.2(3) . . . . ? O5B C6B C7B Br1B -3.9(3) . . . . ? C11B C6B C7B Br1B 178.48(17) . . . . ? C6B C7B C8B C9B -0.8(4) . . . . ? Br1B C7B C8B C9B -178.06(17) . . . . ? C7B C8B C9B C10B -0.4(4) . . . . ? C7B C8B C9B Br2B 177.19(17) . . . . ? C8B C9B C10B O2B -179.5(2) . . . . ? Br2B C9B C10B O2B 2.9(3) . . . . ? C8B C9B C10B C11B 1.1(3) . . . . ? Br2B C9B C10B C11B -176.48(16) . . . . ? O5B C6B C11B C10B -177.9(2) . . . . ? C7B C6B C11B C10B -0.5(3) . . . . ? O5B C6B C11B C12B 2.9(3) . . . . ? C7B C6B C11B C12B -179.6(2) . . . . ? O2B C10B C11B C6B 179.9(2) . . . . ? C9B C10B C11B C6B -0.7(3) . . . . ? O2B C10B C11B C12B -0.9(3) . . . . ? C9B C10B C11B C12B 178.4(2) . . . . ? C6B C11B C12B O3B -177.0(2) . . . . ? C10B C11B C12B O3B 3.9(3) . . . . ? C6B C11B C12B C13B 2.7(3) . . . . ? C10B C11B C12B C13B -176.5(2) . . . . ? O3B C12B C13B C4B -162.2(2) . . . . ? C11B C12B C13B C4B 18.2(3) . . . . ? O3B C12B C13B C1B 78.0(3) . . . . ? C11B C12B C13B C1B -101.6(2) . . . . ? O5B C4B C13B C12B -42.9(3) . . . . ? C3B C4B C13B C12B -157.63(19) . . . . ? O5B C4B C13B C1B 82.3(2) . . . . ? C3B C4B C13B C1B -32.4(2) . . . . ? O1B C1B C13B C12B -72.0(2) . . . . ? C2B C1B C13B C12B 166.02(18) . . . . ? O1B C1B C13B C4B 162.49(17) . . . . ? C2B C1B C13B C4B 40.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.682 _refine_diff_density_min -0.638 _refine_diff_density_rms 0.077 #===END data_13 _database_code_depnum_ccdc_archive 'CCDC 859791' #TrackingRef '- CIFS_8_10_13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Br2 O4' _chemical_formula_sum 'C12 H10 Br2 O4' _chemical_formula_weight 378.02 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 13.574(6) _cell_length_b 17.699(8) _cell_length_c 21.533(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5173(4) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9735 _cell_measurement_theta_min 2.325 _cell_measurement_theta_max 19.125 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 6.271 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2176 _exptl_absorpt_correction_T_max 0.8342 _exptl_absorpt_process_details 'bruker 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 'CCD Area Detector' _diffrn_measurement_device 'BRUKER SMART APEX II' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 79943 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.27 _reflns_number_total 9365 _reflns_number_gt 6701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, ORTEP3' _computing_publication_material 'SHELXTL, PLATON' _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^)+(0.0071P)^2^+2.3027P] 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 0.003(6) _refine_ls_number_reflns 9365 _refine_ls_number_parameters 657 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0589 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 0.34858(4) 0.38359(3) 0.11246(3) 0.06354(17) Uani 1 1 d . . . Br2A Br 0.15249(5) 0.27997(4) 0.32924(3) 0.08062(19) Uani 1 1 d . . . O1A O 0.4132(3) 0.5781(2) 0.28447(19) 0.0764(11) Uani 1 1 d . . . H1A H 0.4632 0.5868 0.3064 0.115 Uiso 1 1 calc R . . O2A O 0.1305(3) 0.4505(2) 0.35038(16) 0.0686(11) Uani 1 1 d . . . H2A H 0.1335 0.4969 0.3583 0.103 Uiso 1 1 calc R . . O3A O 0.1646(3) 0.5923(2) 0.33047(17) 0.0793(12) Uani 1 1 d . . . O5A O 0.3022(2) 0.5347(2) 0.16741(15) 0.0552(9) Uani 1 1 d . . . C1A C 0.3701(4) 0.6483(3) 0.2651(3) 0.0653(16) Uani 1 1 d . . . H1A1 H 0.3726 0.6864 0.2993 0.078 Uiso 1 1 calc R . . C2A C 0.4197(5) 0.6785(4) 0.2067(3) 0.090(2) Uani 1 1 d . . . H2A2 H 0.4311 0.7336 0.2107 0.108 Uiso 1 1 calc R . . H2A1 H 0.4841 0.6534 0.2006 0.108 Uiso 1 1 calc R . . C3A C 0.3538(4) 0.6631(3) 0.1525(3) 0.0788(18) Uani 1 1 d . . . H3A1 H 0.3909 0.6374 0.1190 0.095 Uiso 1 1 calc R . . H3A2 H 0.3266 0.7109 0.1359 0.095 Uiso 1 1 calc R . . C4A C 0.2715(4) 0.6127(3) 0.1761(2) 0.0579(14) Uani 1 1 d . . . H4A H 0.2086 0.6231 0.1535 0.070 Uiso 1 1 calc R . . C6A C 0.2655(3) 0.4796(3) 0.2047(2) 0.0461(13) Uani 1 1 d . . . C7A C 0.2794(3) 0.4049(3) 0.1865(2) 0.0495(13) Uani 1 1 d . . . C8A C 0.2451(4) 0.3467(3) 0.2234(3) 0.0573(15) Uani 1 1 d . . . H8A H 0.2561 0.2958 0.2112 0.069 Uiso 1 1 calc R . . C9A C 0.1946(3) 0.3615(3) 0.2783(2) 0.0507(14) Uani 1 1 d . . . C10A C 0.1785(3) 0.4362(3) 0.2964(2) 0.0534(14) Uani 1 1 d . . . C11A C 0.2152(3) 0.4959(3) 0.2600(2) 0.0448(13) Uani 1 1 d . . . C12A C 0.2087(4) 0.5736(3) 0.2827(2) 0.0560(15) Uani 1 1 d . . . C13A C 0.2626(4) 0.6334(3) 0.2449(2) 0.0568(15) Uani 1 1 d . . . H13A H 0.2251 0.6819 0.2481 0.068 Uiso 1 1 calc R . . Br1B Br -0.01194(4) 0.57361(3) 0.17693(2) 0.05748(15) Uani 1 1 d . . . Br2B Br -0.02855(5) 0.25080(3) 0.16477(3) 0.0823(2) Uani 1 1 d . . . O1B O 0.0208(2) 0.5008(2) -0.06346(15) 0.0588(9) Uani 1 1 d . . . H1B H 0.0009 0.5230 -0.0313 0.088 Uiso 1 1 calc R . . O2B O 0.0991(3) 0.27814(18) 0.05316(16) 0.0616(10) Uani 1 1 d . . . H2B H 0.1346 0.2861 0.0219 0.092 Uiso 1 1 calc R . . O3B O 0.1855(2) 0.3560(2) -0.03136(17) 0.0607(10) Uani 1 1 d . . . O5B O 0.1109(2) 0.55132(18) 0.06137(14) 0.0463(9) Uani 1 1 d . . . C1B C 0.1208(3) 0.5239(3) -0.0767(2) 0.0493(13) Uani 1 1 d . . . H1B1 H 0.1402 0.5058 -0.1190 0.059 Uiso 1 1 calc R . . C2B C 0.1336(4) 0.6106(3) -0.0728(2) 0.0571(14) Uani 1 1 d . . . H2B1 H 0.1669 0.6299 -0.1105 0.069 Uiso 1 1 calc R . . H2B2 H 0.0687 0.6357 -0.0690 0.069 Uiso 1 1 calc R . . C3B C 0.1971(4) 0.6262(3) -0.0146(2) 0.0608(15) Uani 1 1 d . . . H3B2 H 0.2644 0.6417 -0.0268 0.073 Uiso 1 1 calc R . . H3B1 H 0.1674 0.6670 0.0107 0.073 Uiso 1 1 calc R . . C4B C 0.2000(3) 0.5531(3) 0.0217(2) 0.0466(13) Uani 1 1 d . . . H4B H 0.2617 0.5485 0.0468 0.056 Uiso 1 1 calc R . . C6B C 0.0834(3) 0.4820(3) 0.0846(2) 0.0420(12) Uani 1 1 d . . . C7B C 0.0260(3) 0.4815(3) 0.1379(2) 0.0440(12) Uani 1 1 d . . . C8B C -0.0060(3) 0.4121(3) 0.1622(2) 0.0494(12) Uani 1 1 d . . . H8B H -0.0453 0.4115 0.1987 0.059 Uiso 1 1 calc R . . C9B C 0.0184(4) 0.3450(3) 0.1341(2) 0.0498(13) Uani 1 1 d . . . C10B C 0.0760(3) 0.3452(3) 0.0805(2) 0.0473(13) Uani 1 1 d . . . C11B C 0.1089(3) 0.4141(3) 0.0549(2) 0.0418(12) Uani 1 1 d . . . C12B C 0.1645(3) 0.4153(3) -0.0036(2) 0.0452(12) Uani 1 1 d . . . C13B C 0.1935(3) 0.4919(3) -0.0276(2) 0.0480(13) Uani 1 1 d . . . H13B H 0.2597 0.4872 -0.0476 0.058 Uiso 1 1 calc R . . Br1C Br 0.48860(4) 0.41325(3) -0.03444(2) 0.05760(15) Uani 1 1 d . . . Br2C Br 0.47053(5) 0.73420(3) -0.01141(3) 0.07286(18) Uani 1 1 d . . . O1C O 0.5192(3) 0.4729(3) 0.2044(2) 0.0904(13) Uani 1 1 d . . . H1C H 0.4937 0.5024 0.2304 0.136 Uiso 1 1 calc R . . O2C O 0.6039(3) 0.70257(18) 0.09673(16) 0.0657(10) Uani 1 1 d . . . H2C H 0.6356 0.6931 0.1293 0.099 Uiso 1 1 calc R . . O3C O 0.6853(3) 0.6202(2) 0.18078(19) 0.0784(12) Uani 1 1 d . . . O5C O 0.6119(2) 0.42936(18) 0.08096(15) 0.0529(9) Uani 1 1 d . . . C1C C 0.6168(5) 0.4548(3) 0.2231(3) 0.0744(18) Uani 1 1 d . . . H1C1 H 0.6316 0.4742 0.2657 0.089 Uiso 1 1 calc R . . C2C C 0.6323(6) 0.3704(4) 0.2186(3) 0.103(2) Uani 1 1 d . . . H2C1 H 0.6723 0.3531 0.2543 0.123 Uiso 1 1 calc R . . H2C2 H 0.5678 0.3444 0.2205 0.123 Uiso 1 1 calc R . . C3C C 0.6839(5) 0.3499(3) 0.1590(3) 0.084(2) Uani 1 1 d . . . H3C1 H 0.6442 0.3136 0.1345 0.101 Uiso 1 1 calc R . . H3C2 H 0.7493 0.3273 0.1675 0.101 Uiso 1 1 calc R . . C4C C 0.6944(4) 0.4248(3) 0.1245(2) 0.0570(15) Uani 1 1 d . . . H4C H 0.7586 0.4267 0.1017 0.068 Uiso 1 1 calc R . . C6C C 0.5844(3) 0.4993(3) 0.0613(2) 0.0454(13) Uani 1 1 d . . . C7C C 0.5249(3) 0.5035(3) 0.0084(2) 0.0428(12) Uani 1 1 d . . . C8C C 0.4930(3) 0.5733(3) -0.0134(2) 0.0471(12) Uani 1 1 d . . . H8C H 0.4525 0.5755 -0.0493 0.057 Uiso 1 1 calc R . . C9C C 0.5193(3) 0.6394(3) 0.0164(2) 0.0466(12) Uani 1 1 d . . . C10C C 0.5789(3) 0.6373(3) 0.0686(2) 0.0465(13) Uani 1 1 d . . . C11C C 0.6097(3) 0.5661(3) 0.0925(2) 0.0440(12) Uani 1 1 d . . . C12C C 0.6640(4) 0.5629(3) 0.1515(2) 0.0537(14) Uani 1 1 d . . . C13C C 0.6912(4) 0.4853(3) 0.1741(3) 0.0562(14) Uani 1 1 d . . . H13C H 0.7576 0.4882 0.1940 0.067 Uiso 1 1 calc R . . Br1D Br 0.34979(4) -0.08868(3) -0.03573(2) 0.05358(14) Uani 1 1 d . . . Br2D Br 0.12479(5) -0.19410(4) 0.17018(4) 0.1013(3) Uani 1 1 d . . . O1D O 0.4229(3) 0.0956(2) 0.14496(16) 0.0737(11) Uani 1 1 d . . . H1D H 0.4350 0.0666 0.1151 0.111 Uiso 1 1 calc R . . O2D O 0.1263(3) -0.0282(2) 0.20107(17) 0.0841(13) Uani 1 1 d . . . H2D H 0.1304 0.0176 0.2111 0.126 Uiso 1 1 calc R . . O3D O 0.1746(3) 0.1137(2) 0.18885(17) 0.0810(12) Uani 1 1 d . . . O5D O 0.3105(2) 0.06139(18) 0.02441(14) 0.0483(9) Uani 1 1 d . . . C1D C 0.3819(4) 0.1654(3) 0.1218(3) 0.0707(17) Uani 1 1 d . . . H1D1 H 0.3875 0.2048 0.1549 0.085 Uiso 1 1 calc R . . C2D C 0.4338(4) 0.1940(3) 0.0633(3) 0.0755(18) Uani 1 1 d . . . H2D2 H 0.4906 0.1614 0.0528 0.091 Uiso 1 1 calc R . . H2D1 H 0.4576 0.2464 0.0693 0.091 Uiso 1 1 calc R . . C3D C 0.3560(4) 0.1910(3) 0.0117(2) 0.0639(15) Uani 1 1 d . . . H6D H 0.3295 0.2421 0.0033 0.077 Uiso 1 1 calc R . . H3D1 H 0.3850 0.1709 -0.0271 0.077 Uiso 1 1 calc R . . C4D C 0.2762(4) 0.1397(3) 0.0350(2) 0.0497(13) Uani 1 1 d . . . H4D H 0.2118 0.1498 0.0139 0.060 Uiso 1 1 calc R . . C6D C 0.2675(3) 0.0060(3) 0.0583(2) 0.0420(12) Uani 1 1 d . . . C7D C 0.2770(3) -0.0689(3) 0.0375(2) 0.0460(12) Uani 1 1 d . . . C8D C 0.2358(3) -0.1273(3) 0.0709(2) 0.0541(14) Uani 1 1 d . . . H8D H 0.2431 -0.1777 0.0565 0.065 Uiso 1 1 calc R . . C9D C 0.1838(4) -0.1138(4) 0.1253(3) 0.0631(16) Uani 1 1 d . . . C10D C 0.1744(4) -0.0396(4) 0.1472(2) 0.0585(16) Uani 1 1 d . . . C11D C 0.2176(3) 0.0211(3) 0.1145(2) 0.0504(14) Uani 1 1 d . . . C12D C 0.2176(4) 0.0983(4) 0.1395(2) 0.0584(16) Uani 1 1 d . . . C13D C 0.2714(4) 0.1565(3) 0.1038(2) 0.0548(15) Uani 1 1 d . . . H13D H 0.2377 0.2062 0.1099 0.066 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 0.0533(3) 0.0808(4) 0.0565(3) -0.0228(3) 0.0097(3) 0.0096(3) Br2A 0.0771(4) 0.0827(4) 0.0821(5) 0.0112(4) 0.0055(4) -0.0071(4) O1A 0.070(3) 0.075(3) 0.084(3) -0.004(2) -0.034(2) 0.002(2) O2A 0.074(3) 0.082(3) 0.049(2) -0.008(2) 0.013(2) 0.010(2) O3A 0.114(3) 0.076(3) 0.049(2) -0.015(2) 0.023(2) 0.023(3) O5A 0.060(2) 0.068(3) 0.038(2) -0.011(2) -0.0005(18) 0.0129(19) C1A 0.082(5) 0.050(4) 0.064(4) -0.015(3) -0.015(4) 0.003(3) C2A 0.097(5) 0.073(5) 0.101(6) 0.003(4) -0.002(5) -0.015(4) C3A 0.076(4) 0.089(5) 0.072(4) -0.002(4) 0.016(4) -0.010(4) C4A 0.061(3) 0.064(4) 0.049(3) 0.002(3) 0.007(3) 0.012(3) C6A 0.041(3) 0.060(4) 0.038(3) -0.004(3) -0.001(3) 0.010(3) C7A 0.043(3) 0.063(4) 0.042(3) -0.015(3) -0.002(2) 0.010(3) C8A 0.044(3) 0.068(4) 0.059(4) -0.016(3) -0.006(3) 0.015(3) C9A 0.045(3) 0.061(4) 0.046(3) 0.001(3) 0.000(3) 0.007(3) C10A 0.041(3) 0.084(4) 0.035(3) -0.004(3) 0.002(2) 0.014(3) C11A 0.042(3) 0.063(4) 0.030(3) -0.005(3) -0.002(2) 0.011(3) C12A 0.058(3) 0.072(4) 0.038(3) -0.010(3) -0.006(3) 0.017(3) C13A 0.071(4) 0.056(4) 0.044(3) -0.010(3) 0.005(3) 0.023(3) Br1B 0.0564(3) 0.0646(4) 0.0514(3) -0.0149(3) 0.0075(3) 0.0058(3) Br2B 0.1076(5) 0.0597(4) 0.0796(4) 0.0162(3) 0.0263(4) 0.0021(4) O1B 0.0433(19) 0.073(3) 0.060(2) -0.0037(19) -0.0019(18) -0.0029(19) O2B 0.073(3) 0.048(2) 0.063(3) 0.0001(19) 0.008(2) 0.0145(19) O3B 0.064(2) 0.056(2) 0.062(2) -0.012(2) 0.022(2) 0.0094(18) O5B 0.0412(18) 0.049(2) 0.049(2) -0.0097(17) 0.0091(17) -0.0021(16) C1B 0.049(3) 0.056(3) 0.042(3) -0.007(3) 0.010(3) -0.002(3) C2B 0.065(3) 0.058(3) 0.049(3) -0.003(3) 0.002(3) -0.007(3) C3B 0.050(3) 0.063(4) 0.069(4) -0.001(3) 0.012(3) -0.014(3) C4B 0.035(3) 0.057(3) 0.048(3) -0.009(3) 0.005(3) -0.006(2) C6B 0.032(3) 0.050(3) 0.044(3) -0.003(3) -0.005(2) 0.001(2) C7B 0.032(3) 0.059(3) 0.041(3) -0.009(2) 0.003(3) 0.005(3) C8B 0.044(3) 0.061(3) 0.043(3) 0.001(3) 0.003(2) 0.005(3) C9B 0.049(3) 0.051(3) 0.050(3) 0.003(3) 0.006(3) 0.000(3) C10B 0.040(3) 0.048(3) 0.054(4) -0.003(3) -0.002(3) 0.012(3) C11B 0.032(2) 0.051(3) 0.042(3) -0.005(3) -0.003(2) 0.005(3) C12B 0.033(3) 0.059(3) 0.044(3) -0.009(3) 0.002(2) 0.007(3) C13B 0.038(3) 0.058(3) 0.048(3) -0.008(3) 0.008(3) -0.002(2) Br1C 0.0581(3) 0.0599(3) 0.0548(3) -0.0131(3) -0.0031(3) -0.0074(3) Br2C 0.0838(4) 0.0566(4) 0.0782(4) 0.0121(3) -0.0225(4) -0.0009(3) O1C 0.072(3) 0.104(4) 0.095(3) -0.012(3) 0.007(3) 0.006(3) O2C 0.079(3) 0.048(2) 0.071(3) -0.004(2) -0.022(2) -0.010(2) O3C 0.097(3) 0.063(3) 0.076(3) -0.011(2) -0.036(2) -0.014(2) O5C 0.056(2) 0.047(2) 0.056(2) -0.0020(18) -0.0112(18) 0.0036(18) C1C 0.089(5) 0.080(5) 0.054(4) 0.010(3) -0.017(4) 0.000(4) C2C 0.120(6) 0.079(5) 0.109(6) 0.044(5) 0.003(5) 0.012(5) C3C 0.117(6) 0.068(4) 0.068(5) 0.005(4) -0.015(4) 0.012(4) C4C 0.051(3) 0.061(4) 0.059(4) 0.005(3) -0.001(3) 0.013(3) C6C 0.037(3) 0.051(3) 0.049(3) 0.002(3) -0.001(3) 0.001(3) C7C 0.039(3) 0.051(3) 0.039(3) -0.003(2) 0.003(3) -0.005(3) C8C 0.042(3) 0.059(3) 0.041(3) 0.003(2) -0.007(2) -0.006(3) C9C 0.043(3) 0.051(3) 0.045(3) 0.001(2) -0.004(3) -0.001(3) C10C 0.050(3) 0.046(3) 0.044(3) -0.007(3) 0.000(3) -0.006(3) C11C 0.042(3) 0.046(3) 0.045(3) -0.004(3) -0.007(2) -0.005(2) C12C 0.048(3) 0.057(4) 0.056(4) 0.004(3) -0.008(3) -0.006(3) C13C 0.050(3) 0.065(4) 0.053(4) 0.005(3) -0.020(3) -0.006(3) Br1D 0.0479(3) 0.0571(3) 0.0558(3) -0.0030(3) 0.0057(3) 0.0101(3) Br2D 0.0776(5) 0.1212(6) 0.1050(6) 0.0548(5) 0.0122(4) -0.0120(4) O1D 0.063(2) 0.088(3) 0.070(3) -0.012(2) -0.023(2) 0.024(2) O2D 0.072(3) 0.133(4) 0.047(2) 0.016(3) 0.020(2) 0.011(3) O3D 0.079(3) 0.116(3) 0.048(2) -0.012(2) 0.008(2) 0.027(2) O5D 0.052(2) 0.047(2) 0.046(2) 0.0010(17) 0.0077(17) 0.0083(16) C1D 0.058(4) 0.081(4) 0.074(4) -0.025(4) -0.017(3) 0.026(3) C2D 0.063(4) 0.063(4) 0.101(5) -0.017(4) 0.001(4) 0.005(3) C3D 0.073(4) 0.052(3) 0.067(4) -0.006(3) 0.004(4) 0.008(3) C4D 0.053(3) 0.047(3) 0.049(3) 0.002(3) 0.001(3) 0.015(3) C6D 0.038(3) 0.051(3) 0.037(3) 0.005(3) -0.005(2) 0.006(2) C7D 0.036(3) 0.058(4) 0.044(3) 0.006(3) -0.001(2) 0.008(2) C8D 0.046(3) 0.053(3) 0.062(4) 0.010(3) -0.004(3) 0.008(3) C9D 0.043(3) 0.087(5) 0.060(4) 0.019(4) -0.006(3) 0.002(3) C10D 0.046(3) 0.090(5) 0.039(3) 0.015(3) 0.000(3) 0.011(3) C11D 0.040(3) 0.072(4) 0.040(3) 0.007(3) 0.000(3) 0.019(3) C12D 0.045(3) 0.097(5) 0.034(3) -0.001(3) 0.000(3) 0.033(3) C13D 0.055(3) 0.061(4) 0.049(4) -0.016(3) -0.006(3) 0.026(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 Br1A C7A 1.887(5) . ? Br2A C9A 1.900(5) . ? O1A C1A 1.436(6) . ? O1A H1A 0.8400 . ? O2A C10A 1.356(5) . ? O2A H2A 0.8400 . ? O3A C12A 1.235(5) . ? O5A C6A 1.359(6) . ? O5A C4A 1.453(6) . ? C1A C2A 1.523(8) . ? C1A C13A 1.545(7) . ? C1A H1A1 1.0000 . ? C2A C3A 1.495(7) . ? C2A H2A2 0.9900 . ? C2A H2A1 0.9900 . ? C3A C4A 1.517(7) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C13A 1.531(7) . ? C4A H4A 1.0000 . ? C6A C7A 1.392(7) . ? C6A C11A 1.403(6) . ? C7A C8A 1.383(7) . ? C8A C9A 1.392(7) . ? C8A H8A 0.9500 . ? C9A C10A 1.396(7) . ? C10A C11A 1.407(7) . ? C11A C12A 1.461(7) . ? C12A C13A 1.524(7) . ? C13A H13A 1.0000 . ? Br1B C7B 1.905(5) . ? Br2B C9B 1.902(5) . ? O1B C1B 1.446(5) . ? O1B H1B 0.8400 . ? O2B C10B 1.361(5) . ? O2B H2B 0.8400 . ? O3B C12B 1.240(5) . ? O5B C6B 1.376(5) . ? O5B C4B 1.481(5) . ? C1B C2B 1.547(6) . ? C1B C13B 1.551(6) . ? C1B H1B1 1.0000 . ? C2B C3B 1.545(7) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.512(6) . ? C3B H3B2 0.9900 . ? C3B H3B1 0.9900 . ? C4B C13B 1.519(6) . ? C4B H4B 1.0000 . ? C6B C7B 1.387(6) . ? C6B C11B 1.406(6) . ? C7B C8B 1.404(6) . ? C8B C9B 1.373(6) . ? C8B H8B 0.9500 . ? C9B C10B 1.395(6) . ? C10B C11B 1.412(6) . ? C11B C12B 1.469(6) . ? C12B C13B 1.504(7) . ? C13B H13B 1.0000 . ? Br1C C7C 1.910(5) . ? Br2C C9C 1.901(5) . ? O1C C1C 1.421(7) . ? O1C H1C 0.8400 . ? O2C C10C 1.348(5) . ? O2C H2C 0.8400 . ? O3C C12C 1.228(6) . ? O5C C6C 1.361(6) . ? O5C C4C 1.464(5) . ? C1C C2C 1.511(7) . ? C1C C13C 1.557(7) . ? C1C H1C1 1.0000 . ? C2C C3C 1.507(8) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? C3C C4C 1.527(7) . ? C3C H3C1 0.9900 . ? C3C H3C2 0.9900 . ? C4C C13C 1.512(7) . ? C4C H4C 1.0000 . ? C6C C7C 1.398(6) . ? C6C C11C 1.404(6) . ? C7C C8C 1.390(6) . ? C8C C9C 1.380(6) . ? C8C H8C 0.9500 . ? C9C C10C 1.386(6) . ? C10C C11C 1.423(6) . ? C11C C12C 1.468(6) . ? C12C C13C 1.504(7) . ? C13C H13C 1.0000 . ? Br1D C7D 1.894(5) . ? Br2D C9D 1.895(6) . ? O1D C1D 1.443(6) . ? O1D H1D 0.8400 . ? O2D C10D 1.347(6) . ? O2D H2D 0.8400 . ? O3D C12D 1.243(5) . ? O5D C6D 1.355(5) . ? O5D C4D 1.480(5) . ? C1D C2D 1.529(8) . ? C1D C13D 1.557(7) . ? C1D H1D1 1.0000 . ? C2D C3D 1.533(7) . ? C2D H2D2 0.9900 . ? C2D H2D1 0.9900 . ? C3D C4D 1.501(7) . ? C3D H6D 0.9900 . ? C3D H3D1 0.9900 . ? C4D C13D 1.513(7) . ? C4D H4D 1.0000 . ? C6D C7D 1.405(7) . ? C6D C11D 1.412(6) . ? C7D C8D 1.378(6) . ? C8D C9D 1.388(7) . ? C8D H8D 0.9500 . ? C9D C10D 1.401(8) . ? C10D C11D 1.412(7) . ? C11D C12D 1.469(8) . ? C12D C13D 1.477(7) . ? C13D H13D 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 C1A O1A H1A 109.5 . . ? C10A O2A H2A 109.5 . . ? C6A O5A C4A 120.1(4) . . ? O1A C1A C2A 111.3(5) . . ? O1A C1A C13A 108.7(4) . . ? C2A C1A C13A 104.2(5) . . ? O1A C1A H1A1 110.8 . . ? C2A C1A H1A1 110.8 . . ? C13A C1A H1A1 110.8 . . ? C3A C2A C1A 108.4(5) . . ? C3A C2A H2A2 110.0 . . ? C1A C2A H2A2 110.0 . . ? C3A C2A H2A1 110.0 . . ? C1A C2A H2A1 110.0 . . ? H2A2 C2A H2A1 108.4 . . ? C2A C3A C4A 106.7(5) . . ? C2A C3A H3A1 110.4 . . ? C4A C3A H3A1 110.4 . . ? C2A C3A H3A2 110.4 . . ? C4A C3A H3A2 110.4 . . ? H3A1 C3A H3A2 108.6 . . ? O5A C4A C3A 107.7(4) . . ? O5A C4A C13A 112.0(4) . . ? C3A C4A C13A 103.9(4) . . ? O5A C4A H4A 111.0 . . ? C3A C4A H4A 111.0 . . ? C13A C4A H4A 111.0 . . ? O5A C6A C7A 117.7(4) . . ? O5A C6A C11A 122.2(5) . . ? C7A C6A C11A 120.1(5) . . ? C8A C7A C6A 119.9(5) . . ? C8A C7A Br1A 120.3(4) . . ? C6A C7A Br1A 119.7(4) . . ? C7A C8A C9A 121.0(5) . . ? C7A C8A H8A 119.5 . . ? C9A C8A H8A 119.5 . . ? C8A C9A C10A 119.5(5) . . ? C8A C9A Br2A 119.7(4) . . ? C10A C9A Br2A 120.8(4) . . ? O2A C10A C9A 119.4(5) . . ? O2A C10A C11A 120.5(5) . . ? C9A C10A C11A 120.0(5) . . ? C6A C11A C10A 119.4(5) . . ? C6A C11A C12A 120.5(5) . . ? C10A C11A C12A 119.9(5) . . ? O3A C12A C11A 124.1(5) . . ? O3A C12A C13A 119.5(5) . . ? C11A C12A C13A 116.4(5) . . ? C12A C13A C4A 112.9(4) . . ? C12A C13A C1A 114.9(4) . . ? C4A C13A C1A 103.8(4) . . ? C12A C13A H13A 108.3 . . ? C4A C13A H13A 108.3 . . ? C1A C13A H13A 108.3 . . ? C1B O1B H1B 109.5 . . ? C10B O2B H2B 109.5 . . ? C6B O5B C4B 116.8(4) . . ? O1B C1B C2B 112.0(4) . . ? O1B C1B C13B 111.1(4) . . ? C2B C1B C13B 104.7(4) . . ? O1B C1B H1B1 109.7 . . ? C2B C1B H1B1 109.7 . . ? C13B C1B H1B1 109.7 . . ? C3B C2B C1B 106.5(4) . . ? C3B C2B H2B1 110.4 . . ? C1B C2B H2B1 110.4 . . ? C3B C2B H2B2 110.4 . . ? C1B C2B H2B2 110.4 . . ? H2B1 C2B H2B2 108.6 . . ? C4B C3B C2B 106.3(4) . . ? C4B C3B H3B2 110.5 . . ? C2B C3B H3B2 110.5 . . ? C4B C3B H3B1 110.5 . . ? C2B C3B H3B1 110.5 . . ? H3B2 C3B H3B1 108.7 . . ? O5B C4B C3B 107.2(4) . . ? O5B C4B C13B 110.0(4) . . ? C3B C4B C13B 104.3(4) . . ? O5B C4B H4B 111.7 . . ? C3B C4B H4B 111.7 . . ? C13B C4B H4B 111.7 . . ? O5B C6B C7B 117.4(4) . . ? O5B C6B C11B 121.9(4) . . ? C7B C6B C11B 120.6(5) . . ? C6B C7B C8B 119.2(4) . . ? C6B C7B Br1B 120.7(4) . . ? C8B C7B Br1B 120.1(4) . . ? C9B C8B C7B 121.2(4) . . ? C9B C8B H8B 119.4 . . ? C7B C8B H8B 119.4 . . ? C8B C9B C10B 119.8(5) . . ? C8B C9B Br2B 121.6(4) . . ? C10B C9B Br2B 118.5(4) . . ? O2B C10B C9B 119.0(5) . . ? O2B C10B C11B 120.7(4) . . ? C9B C10B C11B 120.3(4) . . ? C6B C11B C10B 118.9(4) . . ? C6B C11B C12B 120.4(5) . . ? C10B C11B C12B 120.7(4) . . ? O3B C12B C11B 121.3(5) . . ? O3B C12B C13B 122.5(4) . . ? C11B C12B C13B 116.2(4) . . ? C12B C13B C4B 114.7(4) . . ? C12B C13B C1B 113.4(4) . . ? C4B C13B C1B 104.7(4) . . ? C12B C13B H13B 107.9 . . ? C4B C13B H13B 107.9 . . ? C1B C13B H13B 107.9 . . ? C1C O1C H1C 109.5 . . ? C10C O2C H2C 109.5 . . ? C6C O5C C4C 117.4(4) . . ? O1C C1C C2C 109.6(6) . . ? O1C C1C C13C 109.5(4) . . ? C2C C1C C13C 102.0(5) . . ? O1C C1C H1C1 111.8 . . ? C2C C1C H1C1 111.8 . . ? C13C C1C H1C1 111.8 . . ? C3C C2C C1C 111.0(5) . . ? C3C C2C H2C1 109.4 . . ? C1C C2C H2C1 109.4 . . ? C3C C2C H2C2 109.4 . . ? C1C C2C H2C2 109.4 . . ? H2C1 C2C H2C2 108.0 . . ? C2C C3C C4C 104.3(5) . . ? C2C C3C H3C1 110.9 . . ? C4C C3C H3C1 110.9 . . ? C2C C3C H3C2 110.9 . . ? C4C C3C H3C2 110.9 . . ? H3C1 C3C H3C2 108.9 . . ? O5C C4C C13C 113.0(4) . . ? O5C C4C C3C 106.7(4) . . ? C13C C4C C3C 105.6(4) . . ? O5C C4C H4C 110.4 . . ? C13C C4C H4C 110.4 . . ? C3C C4C H4C 110.4 . . ? O5C C6C C7C 117.5(4) . . ? O5C C6C C11C 123.4(4) . . ? C7C C6C C11C 119.1(5) . . ? C8C C7C C6C 120.1(4) . . ? C8C C7C Br1C 120.0(4) . . ? C6C C7C Br1C 119.8(4) . . ? C9C C8C C7C 121.1(4) . . ? C9C C8C H8C 119.5 . . ? C7C C8C H8C 119.5 . . ? C8C C9C C10C 120.3(4) . . ? C8C C9C Br2C 120.8(4) . . ? C10C C9C Br2C 118.8(4) . . ? O2C C10C C9C 119.2(5) . . ? O2C C10C C11C 121.5(4) . . ? C9C C10C C11C 119.3(4) . . ? C6C C11C C10C 120.0(4) . . ? C6C C11C C12C 120.3(5) . . ? C10C C11C C12C 119.6(4) . . ? O3C C12C C11C 122.0(5) . . ? O3C C12C C13C 122.0(5) . . ? C11C C12C C13C 116.0(5) . . ? C12C C13C C4C 115.1(4) . . ? C12C C13C C1C 112.2(5) . . ? C4C C13C C1C 104.6(4) . . ? C12C C13C H13C 108.2 . . ? C4C C13C H13C 108.2 . . ? C1C C13C H13C 108.2 . . ? C1D O1D H1D 109.5 . . ? C10D O2D H2D 109.5 . . ? C6D O5D C4D 117.4(4) . . ? O1D C1D C2D 113.0(4) . . ? O1D C1D C13D 111.8(5) . . ? C2D C1D C13D 105.8(5) . . ? O1D C1D H1D1 108.7 . . ? C2D C1D H1D1 108.7 . . ? C13D C1D H1D1 108.7 . . ? C1D C2D C3D 105.6(4) . . ? C1D C2D H2D2 110.6 . . ? C3D C2D H2D2 110.6 . . ? C1D C2D H2D1 110.6 . . ? C3D C2D H2D1 110.6 . . ? H2D2 C2D H2D1 108.8 . . ? C4D C3D C2D 106.0(5) . . ? C4D C3D H6D 110.5 . . ? C2D C3D H6D 110.5 . . ? C4D C3D H3D1 110.5 . . ? C2D C3D H3D1 110.5 . . ? H6D C3D H3D1 108.7 . . ? O5D C4D C3D 106.8(4) . . ? O5D C4D C13D 110.4(4) . . ? C3D C4D C13D 103.9(4) . . ? O5D C4D H4D 111.8 . . ? C3D C4D H4D 111.8 . . ? C13D C4D H4D 111.8 . . ? O5D C6D C7D 118.1(4) . . ? O5D C6D C11D 122.1(5) . . ? C7D C6D C11D 119.8(5) . . ? C8D C7D C6D 120.2(5) . . ? C8D C7D Br1D 120.6(4) . . ? C6D C7D Br1D 119.2(4) . . ? C7D C8D C9D 121.3(5) . . ? C7D C8D H8D 119.4 . . ? C9D C8D H8D 119.4 . . ? C8D C9D C10D 119.3(5) . . ? C8D C9D Br2D 121.1(5) . . ? C10D C9D Br2D 119.6(5) . . ? O2D C10D C9D 118.3(6) . . ? O2D C10D C11D 121.1(6) . . ? C9D C10D C11D 120.6(5) . . ? C10D C11D C6D 118.8(5) . . ? C10D C11D C12D 121.7(5) . . ? C6D C11D C12D 119.3(5) . . ? O3D C12D C11D 121.1(6) . . ? O3D C12D C13D 121.6(6) . . ? C11D C12D C13D 117.3(5) . . ? C12D C13D C4D 113.1(5) . . ? C12D C13D C1D 114.7(5) . . ? C4D C13D C1D 102.8(4) . . ? C12D C13D H13D 108.6 . . ? C4D C13D H13D 108.6 . . ? C1D C13D H13D 108.6 . . ? 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 O1A C1A C2A C3A 102.9(6) . . . . ? C13A C1A C2A C3A -14.0(6) . . . . ? C1A C2A C3A C4A -8.6(7) . . . . ? C6A O5A C4A C3A 153.5(4) . . . . ? C6A O5A C4A C13A 39.8(6) . . . . ? C2A C3A C4A O5A -91.0(5) . . . . ? C2A C3A C4A C13A 28.0(6) . . . . ? C4A O5A C6A C7A 166.1(4) . . . . ? C4A O5A C6A C11A -14.0(6) . . . . ? O5A C6A C7A C8A 178.8(4) . . . . ? C11A C6A C7A C8A -1.1(7) . . . . ? O5A C6A C7A Br1A 0.6(6) . . . . ? C11A C6A C7A Br1A -179.3(3) . . . . ? C6A C7A C8A C9A 1.4(7) . . . . ? Br1A C7A C8A C9A 179.5(4) . . . . ? C7A C8A C9A C10A -0.1(7) . . . . ? C7A C8A C9A Br2A -177.9(4) . . . . ? C8A C9A C10A O2A -179.1(4) . . . . ? Br2A C9A C10A O2A -1.3(7) . . . . ? C8A C9A C10A C11A -1.6(7) . . . . ? Br2A C9A C10A C11A 176.3(3) . . . . ? O5A C6A C11A C10A 179.6(4) . . . . ? C7A C6A C11A C10A -0.5(7) . . . . ? O5A C6A C11A C12A -6.0(7) . . . . ? C7A C6A C11A C12A 173.9(4) . . . . ? O2A C10A C11A C6A 179.3(4) . . . . ? C9A C10A C11A C6A 1.8(7) . . . . ? O2A C10A C11A C12A 4.9(7) . . . . ? C9A C10A C11A C12A -172.6(4) . . . . ? C6A C11A C12A O3A 178.9(5) . . . . ? C10A C11A C12A O3A -6.7(7) . . . . ? C6A C11A C12A C13A -2.6(6) . . . . ? C10A C11A C12A C13A 171.8(4) . . . . ? O3A C12A C13A C4A -153.3(5) . . . . ? C11A C12A C13A C4A 28.1(6) . . . . ? O3A C12A C13A C1A 87.9(6) . . . . ? C11A C12A C13A C1A -90.7(5) . . . . ? O5A C4A C13A C12A -45.4(6) . . . . ? C3A C4A C13A C12A -161.4(5) . . . . ? O5A C4A C13A C1A 79.6(5) . . . . ? C3A C4A C13A C1A -36.4(5) . . . . ? O1A C1A C13A C12A 35.9(6) . . . . ? C2A C1A C13A C12A 154.7(5) . . . . ? O1A C1A C13A C4A -87.8(5) . . . . ? C2A C1A C13A C4A 30.9(5) . . . . ? O1B C1B C2B C3B 110.3(4) . . . . ? C13B C1B C2B C3B -10.2(5) . . . . ? C1B C2B C3B C4B -12.7(5) . . . . ? C6B O5B C4B C3B 161.8(4) . . . . ? C6B O5B C4B C13B 49.1(5) . . . . ? C2B C3B C4B O5B -85.4(4) . . . . ? C2B C3B C4B C13B 31.2(5) . . . . ? C4B O5B C6B C7B 156.9(4) . . . . ? C4B O5B C6B C11B -25.4(6) . . . . ? O5B C6B C7B C8B 178.2(4) . . . . ? C11B C6B C7B C8B 0.4(7) . . . . ? O5B C6B C7B Br1B -0.3(6) . . . . ? C11B C6B C7B Br1B -178.1(3) . . . . ? C6B C7B C8B C9B 0.0(7) . . . . ? Br1B C7B C8B C9B 178.5(4) . . . . ? C7B C8B C9B C10B 0.0(7) . . . . ? C7B C8B C9B Br2B -177.6(3) . . . . ? C8B C9B C10B O2B -179.7(4) . . . . ? Br2B C9B C10B O2B -2.0(6) . . . . ? C8B C9B C10B C11B -0.3(7) . . . . ? Br2B C9B C10B C11B 177.4(3) . . . . ? O5B C6B C11B C10B -178.4(4) . . . . ? C7B C6B C11B C10B -0.7(6) . . . . ? O5B C6B C11B C12B -1.5(6) . . . . ? C7B C6B C11B C12B 176.2(4) . . . . ? O2B C10B C11B C6B -180.0(4) . . . . ? C9B C10B C11B C6B 0.6(7) . . . . ? O2B C10B C11B C12B 3.1(7) . . . . ? C9B C10B C11B C12B -176.3(4) . . . . ? C6B C11B C12B O3B -178.1(4) . . . . ? C10B C11B C12B O3B -1.3(7) . . . . ? C6B C11B C12B C13B 1.5(6) . . . . ? C10B C11B C12B C13B 178.3(4) . . . . ? O3B C12B C13B C4B -156.3(4) . . . . ? C11B C12B C13B C4B 24.1(6) . . . . ? O3B C12B C13B C1B 83.5(5) . . . . ? C11B C12B C13B C1B -96.1(5) . . . . ? O5B C4B C13B C12B -47.9(5) . . . . ? C3B C4B C13B C12B -162.5(4) . . . . ? O5B C4B C13B C1B 77.0(4) . . . . ? C3B C4B C13B C1B -37.6(5) . . . . ? O1B C1B C13B C12B 34.0(5) . . . . ? C2B C1B C13B C12B 155.1(4) . . . . ? O1B C1B C13B C4B -91.7(4) . . . . ? C2B C1B C13B C4B 29.4(5) . . . . ? O1C C1C C2C C3C 98.2(7) . . . . ? C13C C1C C2C C3C -17.8(7) . . . . ? C1C C2C C3C C4C -3.3(8) . . . . ? C6C O5C C4C C13C 41.6(6) . . . . ? C6C O5C C4C C3C 157.2(4) . . . . ? C2C C3C C4C O5C -96.6(5) . . . . ? C2C C3C C4C C13C 23.9(6) . . . . ? C4C O5C C6C C7C 163.4(4) . . . . ? C4C O5C C6C C11C -18.9(6) . . . . ? O5C C6C C7C C8C 178.9(4) . . . . ? C11C C6C C7C C8C 1.2(7) . . . . ? O5C C6C C7C Br1C -1.7(6) . . . . ? C11C C6C C7C Br1C -179.5(3) . . . . ? C6C C7C C8C C9C 0.2(7) . . . . ? Br1C C7C C8C C9C -179.2(3) . . . . ? C7C C8C C9C C10C 0.5(7) . . . . ? C7C C8C C9C Br2C -177.1(3) . . . . ? C8C C9C C10C O2C 179.7(4) . . . . ? Br2C C9C C10C O2C -2.6(6) . . . . ? C8C C9C C10C C11C -2.3(7) . . . . ? Br2C C9C C10C C11C 175.3(3) . . . . ? O5C C6C C11C C10C 179.4(4) . . . . ? C7C C6C C11C C10C -3.0(7) . . . . ? O5C C6C C11C C12C -3.5(7) . . . . ? C7C C6C C11C C12C 174.1(4) . . . . ? O2C C10C C11C C6C -178.5(4) . . . . ? C9C C10C C11C C6C 3.6(7) . . . . ? O2C C10C C11C C12C 4.4(7) . . . . ? C9C C10C C11C C12C -173.5(4) . . . . ? C6C C11C C12C O3C -178.3(5) . . . . ? C10C C11C C12C O3C -1.1(7) . . . . ? C6C C11C C12C C13C 1.3(7) . . . . ? C10C C11C C12C C13C 178.4(4) . . . . ? O3C C12C C13C C4C -158.5(5) . . . . ? C11C C12C C13C C4C 22.0(6) . . . . ? O3C C12C C13C C1C 82.0(6) . . . . ? C11C C12C C13C C1C -97.5(5) . . . . ? O5C C4C C13C C12C -42.7(6) . . . . ? C3C C4C C13C C12C -159.0(5) . . . . ? O5C C4C C13C C1C 80.8(5) . . . . ? C3C C4C C13C C1C -35.4(5) . . . . ? O1C C1C C13C C12C 41.6(6) . . . . ? C2C C1C C13C C12C 157.6(5) . . . . ? O1C C1C C13C C4C -83.9(5) . . . . ? C2C C1C C13C C4C 32.2(6) . . . . ? O1D C1D C2D C3D 115.5(5) . . . . ? C13D C1D C2D C3D -7.1(6) . . . . ? C1D C2D C3D C4D -17.6(6) . . . . ? C6D O5D C4D C3D 159.6(4) . . . . ? C6D O5D C4D C13D 47.3(5) . . . . ? C2D C3D C4D O5D -80.5(5) . . . . ? C2D C3D C4D C13D 36.2(5) . . . . ? C4D O5D C6D C7D 162.0(4) . . . . ? C4D O5D C6D C11D -20.6(6) . . . . ? O5D C6D C7D C8D 179.0(4) . . . . ? C11D C6D C7D C8D 1.5(7) . . . . ? O5D C6D C7D Br1D 0.6(6) . . . . ? C11D C6D C7D Br1D -176.9(3) . . . . ? C6D C7D C8D C9D 0.4(7) . . . . ? Br1D C7D C8D C9D 178.8(3) . . . . ? C7D C8D C9D C10D -1.0(7) . . . . ? C7D C8D C9D Br2D 178.6(3) . . . . ? C8D C9D C10D O2D -178.0(4) . . . . ? Br2D C9D C10D O2D 2.4(7) . . . . ? C8D C9D C10D C11D -0.3(8) . . . . ? Br2D C9D C10D C11D -179.9(3) . . . . ? O2D C10D C11D C6D 179.8(4) . . . . ? C9D C10D C11D C6D 2.1(7) . . . . ? O2D C10D C11D C12D 4.0(7) . . . . ? C9D C10D C11D C12D -173.7(5) . . . . ? O5D C6D C11D C10D 179.8(4) . . . . ? C7D C6D C11D C10D -2.8(7) . . . . ? O5D C6D C11D C12D -4.3(6) . . . . ? C7D C6D C11D C12D 173.1(4) . . . . ? C10D C11D C12D O3D -4.1(7) . . . . ? C6D C11D C12D O3D -179.9(4) . . . . ? C10D C11D C12D C13D 175.4(4) . . . . ? C6D C11D C12D C13D -0.4(6) . . . . ? O3D C12D C13D C4D -152.5(4) . . . . ? C11D C12D C13D C4D 28.0(6) . . . . ? O3D C12D C13D C1D 89.9(6) . . . . ? C11D C12D C13D C1D -89.6(5) . . . . ? O5D C4D C13D C12D -50.0(5) . . . . ? C3D C4D C13D C12D -164.1(4) . . . . ? O5D C4D C13D C1D 74.3(5) . . . . ? C3D C4D C13D C1D -39.8(5) . . . . ? O1D C1D C13D C12D 28.7(6) . . . . ? C2D C1D C13D C12D 152.1(5) . . . . ? O1D C1D C13D C4D -94.6(5) . . . . ? C2D C1D C13D C4D 28.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.413 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.063 #===END