# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Wenwei Lin' _publ_contact_author_email migrant0528@gmail.com loop_ _publ_author_name 'Yeong-Jiunn Jang' 'Siang-en Syu' 'Yu-Jhang Chen' 'Mei-Chun Yang' 'Wenwei Lin' data_a11737 _database_code_depnum_ccdc_archive 'CCDC 805741' #TrackingRef 'a11737.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H15 Br O4' _chemical_formula_sum 'C24 H15 Br O4' _chemical_formula_weight 447.27 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 'P 21/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 13.9784(17) _cell_length_b 6.7384(8) _cell_length_c 20.781(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.778(3) _cell_angle_gamma 90.00 _cell_volume 1874.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 2.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3691 _exptl_absorpt_correction_T_max 0.9363 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12265 _diffrn_reflns_av_R_equivalents 0.0552 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3304 _reflns_number_gt 2025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0389P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3304 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0936 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 C1 C 0.2340(2) 0.6942(5) 0.07883(17) 0.0291(8) Uani 1 1 d . . . C2 C 0.3034(3) 0.6882(5) 0.04309(17) 0.0320(9) Uani 1 1 d . . . H2 H 0.2818 0.6890 -0.0047 0.038 Uiso 1 1 calc R . . C3 C 0.4035(2) 0.6810(5) 0.07651(16) 0.0287(8) Uani 1 1 d . . . H3 H 0.4514 0.6779 0.0521 0.034 Uiso 1 1 calc R . . C4 C 0.4340(2) 0.6784(5) 0.14596(16) 0.0250(8) Uani 1 1 d . . . C5 C 0.3662(2) 0.6837(5) 0.18311(15) 0.0224(8) Uani 1 1 d . . . C6 C 0.2648(2) 0.6917(5) 0.14852(16) 0.0275(8) Uani 1 1 d . . . H6 H 0.2166 0.6956 0.1727 0.033 Uiso 1 1 calc R . . C7 C 0.4077(2) 0.6815(5) 0.25599(16) 0.0231(8) Uani 1 1 d . . . C8 C 0.5141(2) 0.6816(4) 0.28524(15) 0.0205(7) Uani 1 1 d . . . C9 C 0.5822(2) 0.6760(5) 0.24408(17) 0.0250(8) Uani 1 1 d . . . C10 C 0.5322(2) 0.6892(5) 0.35430(16) 0.0242(8) Uani 1 1 d . . . C11 C 0.6166(2) 0.6869(5) 0.41493(16) 0.0264(8) Uani 1 1 d . . . C12 C 0.7146(2) 0.6986(5) 0.41290(17) 0.0326(9) Uani 1 1 d . . . H12 H 0.7287 0.7102 0.3710 0.039 Uiso 1 1 calc R . . C13 C 0.7926(3) 0.6933(5) 0.4725(2) 0.0411(10) Uani 1 1 d . . . H13 H 0.8598 0.7011 0.4711 0.049 Uiso 1 1 calc R . . C14 C 0.7730(3) 0.6770(5) 0.5334(2) 0.0475(11) Uani 1 1 d . . . H14 H 0.8265 0.6719 0.5738 0.057 Uiso 1 1 calc R . . C15 C 0.6756(3) 0.6680(5) 0.53572(18) 0.0439(10) Uani 1 1 d . . . H15 H 0.6620 0.6589 0.5778 0.053 Uiso 1 1 calc R . . C16 C 0.5983(3) 0.6722(5) 0.47749(16) 0.0342(9) Uani 1 1 d . . . H16 H 0.5314 0.6652 0.4796 0.041 Uiso 1 1 calc R . . C17 C 0.3655(2) 0.6904(5) 0.30708(15) 0.0246(8) Uani 1 1 d . . . C18 C 0.2651(2) 0.6959(5) 0.31405(15) 0.0247(8) Uani 1 1 d . . . C19 C 0.1957(2) 0.5490(5) 0.28633(16) 0.0327(9) Uani 1 1 d . . . H19 H 0.2139 0.4443 0.2616 0.039 Uiso 1 1 calc R . . C20 C 0.1008(2) 0.5518(5) 0.29399(16) 0.0320(9) Uani 1 1 d . . . H20 H 0.0537 0.4523 0.2735 0.038 Uiso 1 1 calc R . . C21 C 0.0751(2) 0.6989(6) 0.33126(16) 0.0304(9) Uani 1 1 d . . . C22 C 0.1430(3) 0.8468(5) 0.35925(16) 0.0358(10) Uani 1 1 d . . . H22 H 0.1244 0.9500 0.3844 0.043 Uiso 1 1 calc R . . C23 C 0.2370(2) 0.8455(5) 0.35102(16) 0.0328(9) Uani 1 1 d . . . H23 H 0.2831 0.9475 0.3707 0.039 Uiso 1 1 calc R . . C24 C -0.0856(2) 0.5593(7) 0.3189(2) 0.0581(12) Uani 1 1 d . . . H24A H -0.1474 0.5874 0.3305 0.087 Uiso 1 1 calc R . . H24B H -0.0570 0.4340 0.3397 0.087 Uiso 1 1 calc R . . H24C H -0.1003 0.5490 0.2700 0.087 Uiso 1 1 calc R . . O1 O 0.53682(15) 0.6739(3) 0.17539(10) 0.0280(6) Uani 1 1 d . . . O2 O 0.67161(16) 0.6737(3) 0.26110(11) 0.0339(6) Uani 1 1 d . . . O3 O 0.44170(15) 0.6947(3) 0.36673(10) 0.0261(5) Uani 1 1 d . . . O4 O -0.01623(17) 0.7151(4) 0.34283(12) 0.0451(7) Uani 1 1 d . . . Br1 Br 0.09670(3) 0.69755(6) 0.033008(19) 0.04875(17) 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 C1 0.033(2) 0.021(2) 0.028(2) -0.0021(17) 0.0012(17) -0.0014(17) C2 0.049(2) 0.028(2) 0.0169(19) 0.0006(17) 0.0057(18) -0.0021(19) C3 0.036(2) 0.027(2) 0.023(2) 0.0012(17) 0.0085(17) -0.0064(18) C4 0.029(2) 0.020(2) 0.025(2) 0.0004(17) 0.0061(17) 0.0004(17) C5 0.026(2) 0.020(2) 0.0201(19) 0.0000(16) 0.0053(16) 0.0004(16) C6 0.030(2) 0.029(2) 0.023(2) -0.0009(17) 0.0065(17) -0.0010(17) C7 0.0239(19) 0.021(2) 0.024(2) 0.0002(16) 0.0063(16) 0.0003(16) C8 0.0206(18) 0.0185(19) 0.0214(19) 0.0005(16) 0.0044(15) -0.0021(16) C9 0.028(2) 0.019(2) 0.028(2) -0.0017(16) 0.0085(17) -0.0034(17) C10 0.0231(19) 0.021(2) 0.029(2) 0.0004(17) 0.0090(16) 0.0004(16) C11 0.029(2) 0.022(2) 0.024(2) -0.0011(17) 0.0011(16) 0.0026(17) C12 0.031(2) 0.030(2) 0.034(2) 0.0004(18) 0.0029(18) 0.0033(18) C13 0.034(2) 0.030(2) 0.048(3) -0.003(2) -0.006(2) -0.0020(19) C14 0.055(3) 0.038(3) 0.032(3) 0.000(2) -0.015(2) 0.004(2) C15 0.056(3) 0.041(3) 0.027(2) -0.0010(19) 0.001(2) -0.003(2) C16 0.041(2) 0.033(2) 0.026(2) -0.0012(18) 0.0054(18) -0.0018(18) C17 0.0230(19) 0.029(2) 0.0190(19) 0.0015(17) 0.0007(16) 0.0014(17) C18 0.0235(19) 0.034(2) 0.0179(18) -0.0009(18) 0.0075(15) 0.0005(18) C19 0.034(2) 0.035(2) 0.032(2) -0.0052(18) 0.0140(17) 0.0019(18) C20 0.022(2) 0.042(3) 0.031(2) -0.0037(19) 0.0063(17) -0.0085(17) C21 0.021(2) 0.048(2) 0.023(2) 0.003(2) 0.0082(16) 0.005(2) C22 0.036(2) 0.044(3) 0.030(2) -0.0115(18) 0.0135(18) 0.0062(19) C23 0.032(2) 0.041(3) 0.026(2) -0.0067(18) 0.0088(17) -0.0022(18) C24 0.029(2) 0.085(4) 0.065(3) -0.006(3) 0.021(2) -0.007(2) O1 0.0257(13) 0.0388(16) 0.0202(13) 0.0016(11) 0.0079(11) -0.0014(11) O2 0.0224(14) 0.0470(18) 0.0330(15) 0.0014(12) 0.0093(11) -0.0016(12) O3 0.0256(13) 0.0326(14) 0.0196(13) -0.0005(11) 0.0057(11) 0.0015(11) O4 0.0281(15) 0.067(2) 0.0428(16) -0.0060(14) 0.0147(13) 0.0023(13) Br1 0.0365(3) 0.0621(3) 0.0370(3) -0.0048(2) -0.00630(18) -0.0001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(4) . ? C1 C6 1.387(4) . ? C1 Br1 1.880(3) . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 O1 1.391(4) . ? C5 C6 1.393(4) . ? C5 C7 1.457(4) . ? C6 H6 0.9500 . ? C7 C17 1.357(4) . ? C7 C8 1.435(4) . ? C8 C10 1.385(4) . ? C8 C9 1.453(4) . ? C9 O2 1.196(3) . ? C9 O1 1.385(4) . ? C10 O3 1.363(3) . ? C10 C11 1.457(4) . ? C11 C12 1.385(4) . ? C11 C16 1.399(4) . ? C12 C13 1.395(5) . ? C12 H12 0.9500 . ? C13 C14 1.373(5) . ? C13 H13 0.9500 . ? C14 C15 1.377(5) . ? C14 H14 0.9500 . ? C15 C16 1.371(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O3 1.382(3) . ? C17 C18 1.452(4) . ? C18 C19 1.389(4) . ? C18 C23 1.391(4) . ? C19 C20 1.381(4) . ? C19 H19 0.9500 . ? C20 C21 1.368(4) . ? C20 H20 0.9500 . ? C21 O4 1.371(4) . ? C21 C22 1.383(4) . ? C22 C23 1.373(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O4 1.418(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.4(3) . . ? C2 C1 Br1 120.0(3) . . ? C6 C1 Br1 119.6(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 121.8(3) . . ? C3 C4 O1 115.3(3) . . ? C5 C4 O1 122.8(3) . . ? C4 C5 C6 118.1(3) . . ? C4 C5 C7 116.6(3) . . ? C6 C5 C7 125.3(3) . . ? C1 C6 C5 120.2(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C17 C7 C8 107.5(3) . . ? C17 C7 C5 132.8(3) . . ? C8 C7 C5 119.6(3) . . ? C10 C8 C7 107.2(3) . . ? C10 C8 C9 131.0(3) . . ? C7 C8 C9 121.7(3) . . ? O2 C9 O1 115.7(3) . . ? O2 C9 C8 129.2(3) . . ? O1 C9 C8 115.1(3) . . ? O3 C10 C8 107.2(3) . . ? O3 C10 C11 113.6(3) . . ? C8 C10 C11 139.1(3) . . ? C12 C11 C16 118.7(3) . . ? C12 C11 C10 122.3(3) . . ? C16 C11 C10 119.0(3) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.8(3) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C7 C17 O3 107.8(3) . . ? C7 C17 C18 136.9(3) . . ? O3 C17 C18 115.3(3) . . ? C19 C18 C23 118.1(3) . . ? C19 C18 C17 121.3(3) . . ? C23 C18 C17 120.6(3) . . ? C20 C19 C18 121.4(3) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 119.5(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? O4 C21 C20 124.5(3) . . ? O4 C21 C22 115.4(3) . . ? C20 C21 C22 120.0(3) . . ? C23 C22 C21 120.5(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C18 120.4(3) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C9 O1 C4 124.1(2) . . ? C10 O3 C17 110.3(2) . . ? C21 O4 C24 117.2(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.404 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.067 data_a12122 _database_code_depnum_ccdc_archive 'CCDC 833192' #TrackingRef 'a12122.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H19 Br O3' _chemical_formula_sum 'C33 H19 Br O3' _chemical_formula_weight 543.39 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 8.9178(8) _cell_length_b 11.7133(11) _cell_length_c 12.8242(11) _cell_angle_alpha 100.0540(10) _cell_angle_beta 104.1850(10) _cell_angle_gamma 108.8230(10) _cell_volume 1181.38(18) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.776 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4955 _exptl_absorpt_correction_T_max 0.8152 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7886 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4023 _reflns_number_gt 3492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0347P)^2^+0.6572P] 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 4023 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 C1 C 0.6829(3) -0.0585(2) 0.58879(19) 0.0254(5) Uani 1 1 d . . . C2 C 0.6840(3) -0.1782(2) 0.5623(2) 0.0306(6) Uani 1 1 d . . . H2 H 0.6490 -0.2348 0.6044 0.037 Uiso 1 1 calc R . . C3 C 0.7362(3) -0.2134(2) 0.4746(2) 0.0307(6) Uani 1 1 d . . . H3 H 0.7370 -0.2952 0.4552 0.037 Uiso 1 1 calc R . . C4 C 0.7880(3) -0.1297(2) 0.41383(19) 0.0238(5) Uani 1 1 d . . . C5 C 0.7862(3) -0.0096(2) 0.43901(19) 0.0217(5) Uani 1 1 d . . . C6 C 0.7315(3) 0.0250(2) 0.52892(19) 0.0240(5) Uani 1 1 d . . . H6 H 0.7282 0.1060 0.5483 0.029 Uiso 1 1 calc R . . C7 C 0.8942(3) -0.1076(2) 0.2580(2) 0.0239(5) Uani 1 1 d . . . C8 C 0.8951(3) 0.0179(2) 0.28055(18) 0.0213(5) Uani 1 1 d . . . C9 C 0.8416(3) 0.0687(2) 0.36820(18) 0.0212(5) Uani 1 1 d . . . C10 C 0.8520(3) 0.1848(2) 0.35970(18) 0.0214(5) Uani 1 1 d . . . C11 C 0.8084(3) 0.2859(2) 0.41235(19) 0.0230(5) Uani 1 1 d . . . C12 C 0.8715(4) 0.3407(2) 0.5267(2) 0.0319(6) Uani 1 1 d . . . H12 H 0.9440 0.3127 0.5735 0.038 Uiso 1 1 calc R . . C13 C 0.8279(4) 0.4370(2) 0.5725(2) 0.0434(8) Uani 1 1 d . . . H13 H 0.8725 0.4758 0.6508 0.052 Uiso 1 1 calc R . . C14 C 0.7210(4) 0.4765(2) 0.5053(3) 0.0429(8) Uani 1 1 d . . . H14 H 0.6886 0.5402 0.5376 0.052 Uiso 1 1 calc R . . C15 C 0.6607(4) 0.4235(2) 0.3909(2) 0.0385(7) Uani 1 1 d . . . H15 H 0.5888 0.4521 0.3443 0.046 Uiso 1 1 calc R . . C16 C 0.7048(3) 0.3291(2) 0.3445(2) 0.0291(6) Uani 1 1 d . . . H16 H 0.6641 0.2933 0.2657 0.035 Uiso 1 1 calc R . . C17 C 0.9372(3) 0.1058(2) 0.22433(19) 0.0226(5) Uani 1 1 d . . . C18 C 1.0043(3) 0.1096(2) 0.13277(19) 0.0250(5) Uani 1 1 d . . . H18 H 1.0371 0.0424 0.1095 0.030 Uiso 1 1 calc R . . C19 C 1.0255(3) 0.1964(2) 0.0771(2) 0.0261(5) Uani 1 1 d . . . H19 H 1.0773 0.1864 0.0215 0.031 Uiso 1 1 calc R . . C20 C 0.9779(3) 0.3067(2) 0.09173(18) 0.0218(5) Uani 1 1 d . . . C21 C 0.8086(3) 0.2920(2) 0.06043(19) 0.0246(5) Uani 1 1 d . . . C22 C 0.6746(3) 0.1717(2) 0.0091(2) 0.0314(6) Uani 1 1 d . . . H22 H 0.6997 0.0988 -0.0051 0.038 Uiso 1 1 calc R . . C23 C 0.5126(4) 0.1602(3) -0.0198(2) 0.0423(7) Uani 1 1 d . . . H23 H 0.4260 0.0796 -0.0551 0.051 Uiso 1 1 calc R . . C24 C 0.4708(3) 0.2662(3) 0.0020(2) 0.0435(7) Uani 1 1 d . . . H24 H 0.3567 0.2564 -0.0163 0.052 Uiso 1 1 calc R . . C25 C 0.5939(3) 0.3823(3) 0.0490(2) 0.0353(6) Uani 1 1 d . . . H25 H 0.5648 0.4534 0.0630 0.042 Uiso 1 1 calc R . . C26 C 0.7655(3) 0.3992(2) 0.07745(19) 0.0259(5) Uani 1 1 d . . . C27 C 0.8921(3) 0.5191(2) 0.12009(19) 0.0260(5) Uani 1 1 d . . . H27 H 0.8631 0.5905 0.1311 0.031 Uiso 1 1 calc R . . C28 C 1.0592(3) 0.5354(2) 0.14657(18) 0.0220(5) Uani 1 1 d . . . C29 C 1.1888(3) 0.6584(2) 0.18962(19) 0.0279(6) Uani 1 1 d . . . H29 H 1.1599 0.7300 0.1974 0.034 Uiso 1 1 calc R . . C30 C 1.3523(3) 0.6737(2) 0.2194(2) 0.0315(6) Uani 1 1 d . . . H30 H 1.4370 0.7558 0.2479 0.038 Uiso 1 1 calc R . . C31 C 1.3970(3) 0.5688(2) 0.2084(2) 0.0314(6) Uani 1 1 d . . . H31 H 1.5120 0.5808 0.2297 0.038 Uiso 1 1 calc R . . C32 C 1.2779(3) 0.4499(2) 0.16770(19) 0.0259(5) Uani 1 1 d . . . H32 H 1.3112 0.3804 0.1617 0.031 Uiso 1 1 calc R . . C33 C 1.1045(3) 0.4284(2) 0.13401(18) 0.0208(5) Uani 1 1 d . . . O1 O 0.9342(2) -0.15795(15) 0.18538(14) 0.0316(4) Uani 1 1 d . . . O2 O 0.8390(2) -0.17619(14) 0.32728(14) 0.0287(4) Uani 1 1 d . . . O3 O 0.9108(2) 0.20750(14) 0.27181(13) 0.0241(4) Uani 1 1 d . . . Br1 Br 0.61790(3) -0.00884(2) 0.71410(2) 0.03235(10) 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 C1 0.0242(13) 0.0262(12) 0.0238(13) 0.0088(10) 0.0079(10) 0.0059(10) C2 0.0350(15) 0.0227(12) 0.0314(14) 0.0131(11) 0.0107(11) 0.0046(11) C3 0.0403(15) 0.0163(12) 0.0326(14) 0.0099(10) 0.0103(12) 0.0068(11) C4 0.0259(13) 0.0203(12) 0.0223(12) 0.0063(9) 0.0059(10) 0.0064(10) C5 0.0200(12) 0.0189(11) 0.0250(12) 0.0100(9) 0.0054(9) 0.0053(9) C6 0.0244(13) 0.0207(12) 0.0261(13) 0.0086(10) 0.0070(10) 0.0071(10) C7 0.0252(13) 0.0192(11) 0.0244(13) 0.0060(10) 0.0056(10) 0.0069(10) C8 0.0238(12) 0.0180(11) 0.0208(12) 0.0054(9) 0.0055(9) 0.0076(10) C9 0.0237(12) 0.0191(11) 0.0209(12) 0.0068(9) 0.0068(9) 0.0083(10) C10 0.0266(13) 0.0224(12) 0.0199(12) 0.0099(9) 0.0100(9) 0.0114(10) C11 0.0306(13) 0.0171(11) 0.0242(12) 0.0089(9) 0.0137(10) 0.0074(10) C12 0.0518(17) 0.0275(13) 0.0261(14) 0.0157(11) 0.0168(12) 0.0199(12) C13 0.085(2) 0.0293(14) 0.0277(15) 0.0124(12) 0.0306(15) 0.0255(15) C14 0.074(2) 0.0269(14) 0.0531(19) 0.0213(13) 0.0445(17) 0.0282(15) C15 0.0474(17) 0.0317(14) 0.0514(18) 0.0231(13) 0.0218(14) 0.0234(13) C16 0.0367(15) 0.0246(13) 0.0299(14) 0.0114(10) 0.0118(11) 0.0139(11) C17 0.0282(13) 0.0184(11) 0.0233(12) 0.0061(9) 0.0082(10) 0.0116(10) C18 0.0328(14) 0.0193(11) 0.0266(13) 0.0053(10) 0.0133(10) 0.0124(10) C19 0.0344(14) 0.0225(12) 0.0244(13) 0.0059(10) 0.0167(10) 0.0098(11) C20 0.0321(14) 0.0214(12) 0.0165(12) 0.0092(9) 0.0121(10) 0.0108(10) C21 0.0302(14) 0.0261(12) 0.0201(12) 0.0113(10) 0.0122(10) 0.0087(11) C22 0.0346(15) 0.0277(13) 0.0319(14) 0.0134(11) 0.0131(11) 0.0074(11) C23 0.0316(16) 0.0393(16) 0.0441(17) 0.0166(13) 0.0096(13) -0.0021(13) C24 0.0260(15) 0.0580(19) 0.0475(18) 0.0236(15) 0.0145(13) 0.0108(14) C25 0.0340(15) 0.0460(16) 0.0366(15) 0.0192(13) 0.0159(12) 0.0214(13) C26 0.0305(14) 0.0322(13) 0.0208(12) 0.0138(10) 0.0124(10) 0.0130(11) C27 0.0362(14) 0.0245(12) 0.0234(12) 0.0094(10) 0.0122(10) 0.0159(11) C28 0.0290(13) 0.0227(12) 0.0161(12) 0.0078(9) 0.0083(9) 0.0104(10) C29 0.0380(15) 0.0216(12) 0.0235(13) 0.0071(10) 0.0090(11) 0.0107(11) C30 0.0333(15) 0.0226(13) 0.0305(14) 0.0061(11) 0.0064(11) 0.0042(11) C31 0.0251(14) 0.0364(15) 0.0291(14) 0.0109(11) 0.0052(11) 0.0087(12) C32 0.0315(14) 0.0261(12) 0.0254(13) 0.0102(10) 0.0109(10) 0.0149(11) C33 0.0271(13) 0.0214(11) 0.0155(11) 0.0075(9) 0.0089(9) 0.0086(10) O1 0.0418(11) 0.0234(9) 0.0342(10) 0.0068(8) 0.0171(8) 0.0152(8) O2 0.0402(10) 0.0176(8) 0.0315(10) 0.0094(7) 0.0157(8) 0.0109(8) O3 0.0362(10) 0.0186(8) 0.0245(9) 0.0092(7) 0.0158(7) 0.0133(7) Br1 0.03639(16) 0.03081(15) 0.03179(16) 0.01266(11) 0.01728(11) 0.00861(11) _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 C1 C6 1.374(3) . ? C1 C2 1.388(3) . ? C1 Br1 1.899(2) . ? C2 C3 1.367(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 O2 1.389(3) . ? C4 C5 1.394(3) . ? C5 C6 1.404(3) . ? C5 C9 1.459(3) . ? C6 H6 0.9500 . ? C7 O1 1.203(3) . ? C7 O2 1.374(3) . ? C7 C8 1.445(3) . ? C8 C17 1.365(3) . ? C8 C9 1.435(3) . ? C9 C10 1.359(3) . ? C10 O3 1.385(3) . ? C10 C11 1.468(3) . ? C11 C12 1.383(3) . ? C11 C16 1.388(3) . ? C12 C13 1.390(4) . ? C12 H12 0.9500 . ? C13 C14 1.373(4) . ? C13 H13 0.9500 . ? C14 C15 1.381(4) . ? C14 H14 0.9500 . ? C15 C16 1.377(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O3 1.358(3) . ? C17 C18 1.443(3) . ? C18 C19 1.333(3) . ? C18 H18 0.9500 . ? C19 C20 1.481(3) . ? C19 H19 0.9500 . ? C20 C21 1.407(3) . ? C20 C33 1.412(3) . ? C21 C26 1.424(3) . ? C21 C22 1.431(3) . ? C22 C23 1.356(4) . ? C22 H22 0.9500 . ? C23 C24 1.409(4) . ? C23 H23 0.9500 . ? C24 C25 1.358(4) . ? C24 H24 0.9500 . ? C25 C26 1.421(4) . ? C25 H25 0.9500 . ? C26 C27 1.398(3) . ? C27 C28 1.385(3) . ? C27 H27 0.9500 . ? C28 C29 1.432(3) . ? C28 C33 1.431(3) . ? C29 C30 1.356(4) . ? C29 H29 0.9500 . ? C30 C31 1.405(4) . ? C30 H30 0.9500 . ? C31 C32 1.363(3) . ? C31 H31 0.9500 . ? C32 C33 1.422(3) . ? C32 H32 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 C6 C1 C2 121.9(2) . . ? C6 C1 Br1 119.66(19) . . ? C2 C1 Br1 118.45(18) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.1(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? O2 C4 C3 114.7(2) . . ? O2 C4 C5 123.8(2) . . ? C3 C4 C5 121.5(2) . . ? C4 C5 C6 117.8(2) . . ? C4 C5 C9 116.2(2) . . ? C6 C5 C9 126.1(2) . . ? C1 C6 C5 119.8(2) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O1 C7 O2 117.4(2) . . ? O1 C7 C8 127.4(2) . . ? O2 C7 C8 115.2(2) . . ? C17 C8 C9 108.0(2) . . ? C17 C8 C7 128.8(2) . . ? C9 C8 C7 123.2(2) . . ? C10 C9 C8 106.1(2) . . ? C10 C9 C5 135.5(2) . . ? C8 C9 C5 118.3(2) . . ? C9 C10 O3 108.81(19) . . ? C9 C10 C11 137.6(2) . . ? O3 C10 C11 113.45(19) . . ? C12 C11 C16 119.7(2) . . ? C12 C11 C10 121.6(2) . . ? C16 C11 C10 118.7(2) . . ? C11 C12 C13 119.5(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C11 120.3(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? O3 C17 C8 108.1(2) . . ? O3 C17 C18 118.9(2) . . ? C8 C17 C18 133.0(2) . . ? C19 C18 C17 127.5(2) . . ? C19 C18 H18 116.3 . . ? C17 C18 H18 116.3 . . ? C18 C19 C20 127.6(2) . . ? C18 C19 H19 116.2 . . ? C20 C19 H19 116.2 . . ? C21 C20 C33 119.6(2) . . ? C21 C20 C19 121.0(2) . . ? C33 C20 C19 119.3(2) . . ? C20 C21 C26 120.1(2) . . ? C20 C21 C22 122.4(2) . . ? C26 C21 C22 117.6(2) . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 120.9(3) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 119.9(3) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 121.1(3) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C27 C26 C25 121.1(2) . . ? C27 C26 C21 119.6(2) . . ? C25 C26 C21 119.3(2) . . ? C28 C27 C26 121.0(2) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 C28 C29 120.9(2) . . ? C27 C28 C33 120.0(2) . . ? C29 C28 C33 119.0(2) . . ? C30 C29 C28 120.7(2) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 120.3(2) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C32 C31 C30 121.0(2) . . ? C32 C31 H31 119.5 . . ? C30 C31 H31 119.5 . . ? C31 C32 C33 121.0(2) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C20 C33 C32 122.5(2) . . ? C20 C33 C28 119.6(2) . . ? C32 C33 C28 117.9(2) . . ? C7 O2 C4 123.25(18) . . ? C17 O3 C10 108.98(17) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.314 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.056