# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Wenhao Hu' _publ_contact_author_email WHU@CHEM.ECNU.EDU.CN _publ_section_title ; Copper(II)-catalyzed highly diastereoselective three-component reactions of aryldiazoacetates with alcohols and chalcones: an easy access to furan derivatives ; loop_ _publ_author_name 'Wenhao Hu.' 'Liping Yang.' 'Changwei Zhai.' 'Yingguang Zhu.' data_z_7 _database_code_depnum_ccdc_archive 'CCDC 756639' #TrackingRef '7 (CCDC 756639).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 O' _chemical_formula_weight 296.35 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.7124(4) _cell_length_b 19.8082(9) _cell_length_c 20.3303(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3105.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9958 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.23 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32737 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2731 _reflns_number_gt 2442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+1.9915P] 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 2731 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.25474(17) 0.14911(6) 0.30254(6) 0.0417(3) Uani 1 1 d . . . C1 C -0.0161(3) 0.35750(10) 0.28401(10) 0.0447(5) Uani 1 1 d . . . H1A H -0.0710 0.3338 0.2491 0.054 Uiso 1 1 calc R . . C2 C -0.0637(3) 0.42329(10) 0.29695(10) 0.0494(5) Uani 1 1 d . . . H2A H -0.1525 0.4441 0.2717 0.059 Uiso 1 1 calc R . . C3 C 0.0174(3) 0.45877(10) 0.34636(10) 0.0458(5) Uani 1 1 d . . . H3A H -0.0157 0.5040 0.3556 0.055 Uiso 1 1 calc R . . C4 C 0.1472(3) 0.42817(9) 0.38255(9) 0.0415(4) Uani 1 1 d . . . H4A H 0.2051 0.4529 0.4160 0.050 Uiso 1 1 calc R . . C5 C 0.1937(2) 0.36177(9) 0.37041(9) 0.0383(4) Uani 1 1 d . . . H5A H 0.2826 0.3412 0.3958 0.046 Uiso 1 1 calc R . . C6 C 0.1107(2) 0.32504(9) 0.32110(9) 0.0360(4) Uani 1 1 d . . . C7 C 0.0947(2) 0.22459(9) 0.45637(9) 0.0394(4) Uani 1 1 d . . . H7A H 0.0263 0.2606 0.4397 0.047 Uiso 1 1 calc R . . C8 C 0.0885(3) 0.20933(10) 0.52238(10) 0.0472(5) Uani 1 1 d . . . H8A H 0.0171 0.2351 0.5510 0.057 Uiso 1 1 calc R . . C9 C 0.1863(3) 0.15651(11) 0.54716(11) 0.0563(6) Uani 1 1 d . . . H9A H 0.1823 0.1457 0.5927 0.068 Uiso 1 1 calc R . . C10 C 0.2899(3) 0.11954(11) 0.50471(13) 0.0582(6) Uani 1 1 d . . . H10A H 0.3571 0.0832 0.5214 0.070 Uiso 1 1 calc R . . C11 C 0.2969(3) 0.13467(10) 0.43890(11) 0.0477(5) Uani 1 1 d . . . H11A H 0.3683 0.1086 0.4105 0.057 Uiso 1 1 calc R . . C12 C 0.2004(2) 0.18774(9) 0.41357(10) 0.0378(4) Uani 1 1 d . . . C13 C 0.3775(3) 0.06456(10) 0.19884(10) 0.0466(5) Uani 1 1 d . . . H13A H 0.4071 0.0533 0.2429 0.056 Uiso 1 1 calc R . . C14 C 0.4254(3) 0.02227(13) 0.14934(13) 0.0644(7) Uani 1 1 d . . . H14A H 0.4871 -0.0179 0.1594 0.077 Uiso 1 1 calc R . . C15 C 0.3872(4) 0.03631(14) 0.08688(14) 0.0691(7) Uani 1 1 d . . . H15A H 0.4216 0.0062 0.0529 0.083 Uiso 1 1 calc R . . C16 C 0.2979(4) 0.09432(16) 0.07148(10) 0.0746(9) Uani 1 1 d . . . H16A H 0.2717 0.1044 0.0269 0.090 Uiso 1 1 calc R . . C17 C 0.2450(3) 0.13893(12) 0.12202(10) 0.0548(6) Uani 1 1 d . . . H17A H 0.1821 0.1788 0.1118 0.066 Uiso 1 1 calc R . . C18 C 0.2864(2) 0.12361(9) 0.18668(8) 0.0343(4) Uani 1 1 d . . . C19 C 0.2379(2) 0.16899(9) 0.23924(9) 0.0386(4) Uani 1 1 d . . . C20 C 0.1801(2) 0.23273(8) 0.23909(9) 0.0380(4) Uani 1 1 d . . . H20A H 0.1563 0.2586 0.2008 0.046 Uiso 1 1 calc R . . C21 C 0.1599(2) 0.25559(9) 0.30403(9) 0.0396(4) Uani 1 1 d . . . C22 C 0.2051(2) 0.20192(9) 0.34293(10) 0.0387(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0384(7) 0.0384(7) 0.0483(8) -0.0054(6) 0.0027(6) -0.0024(5) C1 0.0429(11) 0.0474(11) 0.0439(11) 0.0051(8) -0.0073(9) -0.0112(9) C2 0.0464(11) 0.0439(11) 0.0579(12) 0.0130(9) -0.0058(10) -0.0011(9) C3 0.0515(11) 0.0367(10) 0.0492(11) 0.0070(8) 0.0104(9) 0.0002(9) C4 0.0488(11) 0.0391(10) 0.0367(9) -0.0012(8) 0.0045(8) -0.0071(8) C5 0.0377(9) 0.0402(10) 0.0372(10) 0.0019(8) -0.0002(8) -0.0027(8) C6 0.0344(9) 0.0352(9) 0.0384(9) 0.0009(7) 0.0051(7) -0.0075(7) C7 0.0361(9) 0.0329(9) 0.0493(11) 0.0017(8) 0.0020(8) -0.0018(7) C8 0.0503(12) 0.0406(11) 0.0508(11) -0.0021(9) 0.0031(9) -0.0112(9) C9 0.0649(14) 0.0524(13) 0.0516(12) 0.0106(10) -0.0124(11) -0.0181(11) C10 0.0489(13) 0.0449(12) 0.0808(16) 0.0097(11) -0.0141(11) 0.0011(10) C11 0.0406(11) 0.0387(10) 0.0637(13) 0.0055(9) 0.0005(9) 0.0015(8) C12 0.0289(9) 0.0300(9) 0.0546(11) -0.0012(8) 0.0000(8) -0.0052(7) C13 0.0446(11) 0.0418(10) 0.0533(12) -0.0057(9) -0.0006(9) 0.0009(9) C14 0.0565(14) 0.0578(14) 0.0788(17) -0.0219(12) 0.0149(13) -0.0006(11) C15 0.0674(16) 0.0675(16) 0.0724(17) -0.0237(13) 0.0281(13) -0.0225(13) C16 0.091(2) 0.106(2) 0.0274(10) -0.0015(12) 0.0025(11) -0.0563(18) C17 0.0631(13) 0.0562(13) 0.0451(12) 0.0113(10) -0.0081(10) -0.0169(11) C18 0.0314(9) 0.0351(9) 0.0364(9) 0.0008(7) 0.0007(7) -0.0082(7) C19 0.0345(9) 0.0416(10) 0.0398(10) -0.0016(8) 0.0021(8) -0.0096(8) C20 0.0393(10) 0.0308(9) 0.0439(10) -0.0030(8) 0.0041(8) -0.0073(7) C21 0.0330(9) 0.0359(9) 0.0497(11) -0.0033(8) 0.0036(8) -0.0072(8) C22 0.0296(9) 0.0384(10) 0.0481(11) -0.0115(8) 0.0060(8) -0.0057(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C19 1.352(2) . ? O1 C22 1.384(2) . ? C1 C2 1.379(3) . ? C1 C6 1.392(3) . ? C1 H1A 0.9500 . ? C2 C3 1.376(3) . ? C2 H2A 0.9500 . ? C3 C4 1.383(3) . ? C3 H3A 0.9500 . ? C4 C5 1.386(3) . ? C4 H4A 0.9500 . ? C5 C6 1.394(3) . ? C5 H5A 0.9500 . ? C6 C21 1.469(3) . ? C7 C8 1.377(3) . ? C7 C12 1.398(3) . ? C7 H7A 0.9500 . ? C8 C9 1.385(3) . ? C8 H8A 0.9500 . ? C9 C10 1.386(3) . ? C9 H9A 0.9500 . ? C10 C11 1.372(3) . ? C10 H10A 0.9500 . ? C11 C12 1.387(3) . ? C11 H11A 0.9500 . ? C12 C22 1.464(3) . ? C13 C14 1.361(3) . ? C13 C18 1.387(3) . ? C13 H13A 0.9500 . ? C14 C15 1.333(4) . ? C14 H14A 0.9500 . ? C15 C16 1.376(4) . ? C15 H15A 0.9500 . ? C16 C17 1.415(4) . ? C16 H16A 0.9500 . ? C17 C18 1.386(3) . ? C17 H17A 0.9500 . ? C18 C19 1.446(3) . ? C19 C20 1.339(3) . ? C20 C21 1.405(3) . ? C20 H20A 0.9500 . ? C21 C22 1.370(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 O1 C22 108.54(15) . . ? C2 C1 C6 121.33(18) . . ? C2 C1 H1A 119.3 . . ? C6 C1 H1A 119.3 . . ? C3 C2 C1 120.06(19) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 119.58(18) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C3 C4 C5 120.59(18) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? C4 C5 C6 120.30(18) . . ? C4 C5 H5A 119.9 . . ? C6 C5 H5A 119.9 . . ? C1 C6 C5 118.10(17) . . ? C1 C6 C21 119.09(17) . . ? C5 C6 C21 122.67(17) . . ? C8 C7 C12 120.81(18) . . ? C8 C7 H7A 119.6 . . ? C12 C7 H7A 119.6 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8A 119.9 . . ? C9 C8 H8A 119.9 . . ? C8 C9 C10 119.1(2) . . ? C8 C9 H9A 120.4 . . ? C10 C9 H9A 120.4 . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 120.4(2) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C12 C7 118.53(19) . . ? C11 C12 C22 119.77(17) . . ? C7 C12 C22 121.65(16) . . ? C14 C13 C18 121.7(2) . . ? C14 C13 H13A 119.2 . . ? C18 C13 H13A 119.2 . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C18 C17 C16 119.0(2) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C17 C18 C13 118.06(19) . . ? C17 C18 C19 120.35(18) . . ? C13 C18 C19 121.58(17) . . ? C20 C19 O1 108.00(16) . . ? C20 C19 C18 132.12(18) . . ? O1 C19 C18 119.84(16) . . ? C19 C20 C21 109.79(17) . . ? C19 C20 H20A 125.1 . . ? C21 C20 H20A 125.1 . . ? C22 C21 C20 105.33(16) . . ? C22 C21 C6 131.01(17) . . ? C20 C21 C6 123.55(17) . . ? C21 C22 O1 108.33(16) . . ? C21 C22 C12 135.15(17) . . ? O1 C22 C12 116.35(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.5(3) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C2 C1 C6 C5 -2.4(3) . . . . ? C2 C1 C6 C21 -178.28(18) . . . . ? C4 C5 C6 C1 1.4(3) . . . . ? C4 C5 C6 C21 177.14(17) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C10 C11 C12 C22 -178.10(18) . . . . ? C8 C7 C12 C11 1.1(3) . . . . ? C8 C7 C12 C22 178.24(17) . . . . ? C18 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C16 C17 C18 C13 -0.4(3) . . . . ? C16 C17 C18 C19 178.49(18) . . . . ? C14 C13 C18 C17 -0.2(3) . . . . ? C14 C13 C18 C19 -179.04(19) . . . . ? C22 O1 C19 C20 0.3(2) . . . . ? C22 O1 C19 C18 178.21(15) . . . . ? C17 C18 C19 C20 -12.8(3) . . . . ? C13 C18 C19 C20 166.1(2) . . . . ? C17 C18 C19 O1 169.91(17) . . . . ? C13 C18 C19 O1 -11.2(3) . . . . ? O1 C19 C20 C21 0.6(2) . . . . ? C18 C19 C20 C21 -176.97(18) . . . . ? C19 C20 C21 C22 -1.2(2) . . . . ? C19 C20 C21 C6 175.36(16) . . . . ? C1 C6 C21 C22 -143.5(2) . . . . ? C5 C6 C21 C22 40.8(3) . . . . ? C1 C6 C21 C20 40.8(3) . . . . ? C5 C6 C21 C20 -134.88(19) . . . . ? C20 C21 C22 O1 1.39(19) . . . . ? C6 C21 C22 O1 -174.84(17) . . . . ? C20 C21 C22 C12 -173.51(19) . . . . ? C6 C21 C22 C12 10.3(3) . . . . ? C19 O1 C22 C21 -1.10(19) . . . . ? C19 O1 C22 C12 174.89(15) . . . . ? C11 C12 C22 C21 -163.4(2) . . . . ? C7 C12 C22 C21 19.4(3) . . . . ? C11 C12 C22 O1 22.0(2) . . . . ? C7 C12 C22 O1 -155.19(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.308 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.043 # Attachment 'cis-9 (CCDC 756904).cif' data_z_cis-9 _database_code_depnum_ccdc_archive 'CCDC 756904' #TrackingRef 'cis-9 (CCDC 756904).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 O3' _chemical_formula_weight 358.42 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 0.0000 '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 0.0000 '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, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.6978(3) _cell_length_b 9.0256(3) _cell_length_c 23.8222(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1870.11(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9997 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9582 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21736 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1903 _reflns_number_gt 1849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.3370P] 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 _chemical_absolute_configuration . _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1903 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.28385(14) 0.16477(13) 0.22309(5) 0.0297(3) Uani 1 1 d . . . O2 O 0.25329(17) 0.39995(15) 0.10462(5) 0.0409(3) Uani 1 1 d . . . O3 O 0.36823(18) 0.42545(14) 0.18791(6) 0.0436(4) Uani 1 1 d . . . C1 C 0.1673(2) -0.1089(2) 0.08919(8) 0.0340(4) Uani 1 1 d . . . H1A H 0.2214 -0.1473 0.1206 0.041 Uiso 1 1 calc R . . C2 C 0.1493(2) -0.1959(2) 0.04177(8) 0.0415(5) Uani 1 1 d . . . H2A H 0.1923 -0.2926 0.0407 0.050 Uiso 1 1 calc R . . C3 C 0.0689(2) -0.1422(2) -0.00389(8) 0.0423(5) Uani 1 1 d . . . H3A H 0.0544 -0.2026 -0.0361 0.051 Uiso 1 1 calc R . . C4 C 0.0101(2) -0.0013(2) -0.00243(8) 0.0426(5) Uani 1 1 d . . . H4A H -0.0448 0.0361 -0.0338 0.051 Uiso 1 1 calc R . . C5 C 0.0305(2) 0.0868(2) 0.04466(7) 0.0340(4) Uani 1 1 d . . . H5A H -0.0091 0.1850 0.0448 0.041 Uiso 1 1 calc R . . C6 C 0.10737(19) 0.0344(2) 0.09150(7) 0.0277(4) Uani 1 1 d . . . C7 C 0.0989(2) 0.1167(2) 0.34894(7) 0.0331(4) Uani 1 1 d . . . H7A H 0.0462 0.2089 0.3482 0.040 Uiso 1 1 calc R . . C8 C 0.1242(2) 0.0462(2) 0.39983(8) 0.0409(5) Uani 1 1 d . . . H8A H 0.0898 0.0907 0.4337 0.049 Uiso 1 1 calc R . . C9 C 0.1990(2) -0.0878(2) 0.40125(8) 0.0392(5) Uani 1 1 d . . . H9A H 0.2177 -0.1354 0.4362 0.047 Uiso 1 1 calc R . . C10 C 0.2470(2) -0.1532(2) 0.35194(8) 0.0390(4) Uani 1 1 d . . . H10A H 0.2968 -0.2469 0.3528 0.047 Uiso 1 1 calc R . . C11 C 0.2226(2) -0.0826(2) 0.30134(8) 0.0352(4) Uani 1 1 d . . . H11A H 0.2561 -0.1281 0.2675 0.042 Uiso 1 1 calc R . . C12 C 0.1494(2) 0.05453(19) 0.29921(7) 0.0289(4) Uani 1 1 d . . . C13 C 0.4596(2) 0.1213(2) 0.08255(8) 0.0332(4) Uani 1 1 d . . . H13A H 0.4021 0.1866 0.0594 0.040 Uiso 1 1 calc R . . C14 C 0.5854(2) 0.0463(2) 0.06063(9) 0.0407(5) Uani 1 1 d . . . H14A H 0.6140 0.0613 0.0226 0.049 Uiso 1 1 calc R . . C15 C 0.6692(2) -0.0496(2) 0.09364(10) 0.0453(5) Uani 1 1 d . . . H15A H 0.7559 -0.0999 0.0786 0.054 Uiso 1 1 calc R . . C16 C 0.6262(2) -0.0722(2) 0.14889(9) 0.0420(5) Uani 1 1 d . . . H16A H 0.6825 -0.1396 0.1716 0.050 Uiso 1 1 calc R . . C17 C 0.5017(2) 0.0030(2) 0.17128(8) 0.0336(4) Uani 1 1 d . . . H17A H 0.4737 -0.0128 0.2094 0.040 Uiso 1 1 calc R . . C18 C 0.41732(19) 0.10102(19) 0.13862(7) 0.0288(4) Uani 1 1 d . . . C19 C 0.1312(2) 0.1347(2) 0.24413(7) 0.0303(4) Uani 1 1 d . . . H19A H 0.0757 0.2302 0.2504 0.036 Uiso 1 1 calc R . . C20 C 0.0558(2) 0.0509(2) 0.19666(7) 0.0349(4) Uani 1 1 d . . . H20A H -0.0576 0.0580 0.1990 0.042 Uiso 1 1 calc R . . H20B H 0.0860 -0.0549 0.1972 0.042 Uiso 1 1 calc R . . C21 C 0.11615(19) 0.12800(19) 0.14395(7) 0.0279(4) Uani 1 1 d . . . H21A H 0.0511 0.2178 0.1376 0.033 Uiso 1 1 calc R . . C22 C 0.2798(2) 0.18330(19) 0.16356(7) 0.0269(4) Uani 1 1 d . . . C23 C 0.29681(19) 0.34846(19) 0.14828(7) 0.0294(4) Uani 1 1 d . . . C24 C 0.3983(4) 0.5799(2) 0.17437(11) 0.0598(7) Uani 1 1 d . . . H24A H 0.4517 0.6272 0.2058 0.090 Uiso 1 1 calc R . . H24B H 0.3007 0.6310 0.1675 0.090 Uiso 1 1 calc R . . H24C H 0.4626 0.5854 0.1407 0.090 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 0.0289(6) 0.0347(6) 0.0256(5) 0.0039(5) -0.0007(5) -0.0041(5) O2 0.0510(8) 0.0371(7) 0.0346(7) 0.0098(6) -0.0011(6) 0.0009(7) O3 0.0600(9) 0.0256(6) 0.0452(7) 0.0030(6) -0.0133(7) -0.0040(7) C1 0.0318(9) 0.0325(9) 0.0376(9) 0.0032(8) -0.0051(8) -0.0008(9) C2 0.0395(10) 0.0328(9) 0.0520(11) -0.0053(9) 0.0026(9) 0.0007(9) C3 0.0452(11) 0.0465(11) 0.0352(9) -0.0099(9) 0.0038(9) -0.0043(10) C4 0.0444(11) 0.0562(12) 0.0270(9) 0.0023(9) -0.0021(8) 0.0037(11) C5 0.0320(9) 0.0383(10) 0.0317(8) 0.0031(8) 0.0006(7) 0.0047(9) C6 0.0218(7) 0.0316(9) 0.0298(8) 0.0027(7) 0.0024(7) -0.0025(7) C7 0.0326(8) 0.0324(9) 0.0342(9) 0.0002(8) 0.0052(7) -0.0014(8) C8 0.0448(11) 0.0479(11) 0.0301(9) 0.0010(9) 0.0041(8) -0.0081(10) C9 0.0355(10) 0.0460(11) 0.0363(9) 0.0130(9) -0.0050(8) -0.0119(9) C10 0.0331(9) 0.0336(9) 0.0503(11) 0.0099(9) -0.0027(9) -0.0018(8) C11 0.0334(9) 0.0345(9) 0.0377(9) 0.0001(8) 0.0048(8) 0.0024(8) C12 0.0245(8) 0.0310(8) 0.0313(8) 0.0016(7) 0.0010(7) -0.0024(8) C13 0.0318(9) 0.0324(9) 0.0355(9) -0.0037(8) 0.0017(7) -0.0043(8) C14 0.0368(9) 0.0398(10) 0.0454(10) -0.0144(9) 0.0086(9) -0.0065(9) C15 0.0296(9) 0.0355(10) 0.0709(14) -0.0179(10) 0.0068(10) 0.0007(9) C16 0.0292(9) 0.0328(9) 0.0641(12) -0.0025(10) -0.0049(9) 0.0031(8) C17 0.0278(8) 0.0293(9) 0.0437(10) 0.0000(7) -0.0036(8) -0.0008(8) C18 0.0244(8) 0.0266(8) 0.0354(9) -0.0025(7) -0.0002(7) -0.0041(7) C19 0.0269(8) 0.0327(9) 0.0313(8) 0.0011(7) 0.0041(7) 0.0042(7) C20 0.0263(8) 0.0459(10) 0.0326(9) 0.0042(8) 0.0005(7) -0.0052(9) C21 0.0241(8) 0.0306(9) 0.0289(8) 0.0021(7) -0.0005(7) 0.0026(7) C22 0.0270(8) 0.0283(8) 0.0253(7) 0.0018(7) -0.0006(7) 0.0004(7) C23 0.0277(8) 0.0296(9) 0.0310(9) 0.0012(8) 0.0044(7) 0.0037(7) C24 0.0883(18) 0.0257(10) 0.0655(14) 0.0061(10) -0.0202(14) -0.0059(12) _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 C22 1.4284(19) . ? O1 C19 1.445(2) . ? O2 C23 1.200(2) . ? O3 C23 1.327(2) . ? O3 C24 1.454(2) . ? C1 C2 1.385(3) . ? C1 C6 1.396(2) . ? C1 H1A 0.9500 . ? C2 C3 1.381(3) . ? C2 H2A 0.9500 . ? C3 C4 1.371(3) . ? C3 H3A 0.9500 . ? C4 C5 1.387(3) . ? C4 H4A 0.9500 . ? C5 C6 1.384(2) . ? C5 H5A 0.9500 . ? C6 C21 1.510(2) . ? C7 C12 1.382(2) . ? C7 C8 1.386(3) . ? C7 H7A 0.9500 . ? C8 C9 1.374(3) . ? C8 H8A 0.9500 . ? C9 C10 1.379(3) . ? C9 H9A 0.9500 . ? C10 C11 1.380(3) . ? C10 H10A 0.9500 . ? C11 C12 1.393(3) . ? C11 H11A 0.9500 . ? C12 C19 1.507(2) . ? C13 C14 1.389(3) . ? C13 C18 1.398(2) . ? C13 H13A 0.9500 . ? C14 C15 1.378(3) . ? C14 H14A 0.9500 . ? C15 C16 1.383(3) . ? C15 H15A 0.9500 . ? C16 C17 1.385(3) . ? C16 H16A 0.9500 . ? C17 C18 1.388(3) . ? C17 H17A 0.9500 . ? C18 C22 1.528(2) . ? C19 C20 1.510(2) . ? C19 H19A 1.0000 . ? C20 C21 1.529(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.579(2) . ? C21 H21A 1.0000 . ? C22 C23 1.542(2) . ? 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 C22 O1 C19 110.12(12) . . ? C23 O3 C24 115.35(16) . . ? C2 C1 C6 121.04(17) . . ? C2 C1 H1A 119.5 . . ? C6 C1 H1A 119.5 . . ? C3 C2 C1 120.06(18) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C4 C3 C2 119.61(18) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 120.34(18) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 121.17(18) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C1 117.74(16) . . ? C5 C6 C21 120.01(16) . . ? C1 C6 C21 122.14(15) . . ? C12 C7 C8 120.87(17) . . ? C12 C7 H7A 119.6 . . ? C8 C7 H7A 119.6 . . ? C9 C8 C7 120.02(18) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C8 C9 C10 119.94(17) . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C9 C10 C11 119.97(18) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C10 C11 C12 120.84(17) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C7 C12 C11 118.32(16) . . ? C7 C12 C19 121.22(16) . . ? C11 C12 C19 120.42(15) . . ? C14 C13 C18 120.19(18) . . ? C14 C13 H13A 119.9 . . ? C18 C13 H13A 119.9 . . ? C15 C14 C13 120.55(19) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C14 C15 C16 119.50(18) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C15 C16 C17 120.39(19) . . ? C15 C16 H16A 119.8 . . ? C17 C16 H16A 119.8 . . ? C16 C17 C18 120.64(18) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C17 C18 C13 118.70(17) . . ? C17 C18 C22 120.37(16) . . ? C13 C18 C22 120.92(16) . . ? O1 C19 C12 107.23(13) . . ? O1 C19 C20 103.51(13) . . ? C12 C19 C20 117.20(15) . . ? O1 C19 H19A 109.5 . . ? C12 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? C19 C20 C21 103.76(14) . . ? C19 C20 H20A 111.0 . . ? C21 C20 H20A 111.0 . . ? C19 C20 H20B 111.0 . . ? C21 C20 H20B 111.0 . . ? H20A C20 H20B 109.0 . . ? C6 C21 C20 114.06(15) . . ? C6 C21 C22 117.85(14) . . ? C20 C21 C22 102.14(13) . . ? C6 C21 H21A 107.4 . . ? C20 C21 H21A 107.4 . . ? C22 C21 H21A 107.4 . . ? O1 C22 C18 108.06(13) . . ? O1 C22 C23 110.21(13) . . ? C18 C22 C23 107.65(14) . . ? O1 C22 C21 106.19(13) . . ? C18 C22 C21 115.90(13) . . ? C23 C22 C21 108.79(14) . . ? O2 C23 O3 124.16(16) . . ? O2 C23 C22 123.29(16) . . ? O3 C23 C22 112.53(14) . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(3) . . . . ? C1 C2 C3 C4 1.4(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? C4 C5 C6 C21 -174.81(17) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C2 C1 C6 C21 175.88(17) . . . . ? C12 C7 C8 C9 -0.6(3) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C8 C9 C10 C11 1.3(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C8 C7 C12 C11 1.7(3) . . . . ? C8 C7 C12 C19 -176.14(18) . . . . ? C10 C11 C12 C7 -1.4(3) . . . . ? C10 C11 C12 C19 176.53(17) . . . . ? C18 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 0.7(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C16 C17 C18 C22 179.87(16) . . . . ? C14 C13 C18 C17 -1.1(3) . . . . ? C14 C13 C18 C22 179.62(16) . . . . ? C22 O1 C19 C12 156.36(13) . . . . ? C22 O1 C19 C20 31.84(18) . . . . ? C7 C12 C19 O1 116.10(17) . . . . ? C11 C12 C19 O1 -61.7(2) . . . . ? C7 C12 C19 C20 -128.16(19) . . . . ? C11 C12 C19 C20 54.0(2) . . . . ? O1 C19 C20 C21 -38.26(17) . . . . ? C12 C19 C20 C21 -156.03(15) . . . . ? C5 C6 C21 C20 124.52(18) . . . . ? C1 C6 C21 C20 -51.8(2) . . . . ? C5 C6 C21 C22 -115.73(18) . . . . ? C1 C6 C21 C22 68.0(2) . . . . ? C19 C20 C21 C6 158.38(14) . . . . ? C19 C20 C21 C22 30.12(17) . . . . ? C19 O1 C22 C18 -137.29(14) . . . . ? C19 O1 C22 C23 105.33(16) . . . . ? C19 O1 C22 C21 -12.33(18) . . . . ? C17 C18 C22 O1 12.5(2) . . . . ? C13 C18 C22 O1 -168.27(15) . . . . ? C17 C18 C22 C23 131.52(17) . . . . ? C13 C18 C22 C23 -49.3(2) . . . . ? C17 C18 C22 C21 -106.46(18) . . . . ? C13 C18 C22 C21 72.8(2) . . . . ? C6 C21 C22 O1 -137.59(15) . . . . ? C20 C21 C22 O1 -11.77(17) . . . . ? C6 C21 C22 C18 -17.6(2) . . . . ? C20 C21 C22 C18 108.21(16) . . . . ? C6 C21 C22 C23 103.81(16) . . . . ? C20 C21 C22 C23 -130.37(15) . . . . ? C24 O3 C23 O2 -2.6(3) . . . . ? C24 O3 C23 C22 175.61(19) . . . . ? O1 C22 C23 O2 -157.29(16) . . . . ? C18 C22 C23 O2 85.1(2) . . . . ? C21 C22 C23 O2 -41.2(2) . . . . ? O1 C22 C23 O3 24.5(2) . . . . ? C18 C22 C23 O3 -93.17(17) . . . . ? C21 C22 C23 O3 140.50(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.135 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.029 # Attachment 'syn-4r (CCDC 756905).cif' data_z_syn-4r _database_code_depnum_ccdc_archive 'CCDC 756905' #TrackingRef 'syn-4r (CCDC 756905).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H27 Br O4' _chemical_formula_weight 543.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.0837(4) _cell_length_b 12.5162(4) _cell_length_c 19.9846(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.7030(10) _cell_angle_gamma 90.00 _cell_volume 2668.91(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9917 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.80 _exptl_crystal_description hexagon _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 1.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606688 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30268 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4691 _reflns_number_gt 3651 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+2.5190P] 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 4691 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.83901(5) 0.17370(5) 0.74645(2) 0.1086(2) Uani 1 1 d . . . O1 O 0.42305(18) 0.11166(17) 0.35772(12) 0.0646(6) Uani 1 1 d . . . O2 O 0.63011(19) 0.13041(18) 0.38316(12) 0.0652(6) Uani 1 1 d . . . O3 O 0.6299(2) 0.55192(18) 0.39829(18) 0.0939(9) Uani 1 1 d . . . O4 O 0.38923(15) 0.24766(15) 0.44719(10) 0.0481(4) Uani 1 1 d . . . C1 C 0.7445(3) 0.1965(3) 0.65326(17) 0.0667(9) Uani 1 1 d . . . C2 C 0.6541(3) 0.2747(3) 0.63802(17) 0.0660(9) Uani 1 1 d . . . H2A H 0.6406 0.3184 0.6730 0.079 Uiso 1 1 calc R . . C3 C 0.5837(3) 0.2876(2) 0.57025(16) 0.0549(7) Uani 1 1 d . . . H3A H 0.5226 0.3405 0.5597 0.066 Uiso 1 1 calc R . . C4 C 0.6022(2) 0.2231(2) 0.51717(14) 0.0453(6) Uani 1 1 d . . . C5 C 0.6953(3) 0.1462(2) 0.53436(17) 0.0562(7) Uani 1 1 d . . . H5A H 0.7102 0.1028 0.4997 0.067 Uiso 1 1 calc R . . C6 C 0.7666(3) 0.1331(3) 0.60258(19) 0.0675(9) Uani 1 1 d . . . H6A H 0.8290 0.0813 0.6135 0.081 Uiso 1 1 calc R . . C7 C 0.2059(3) 0.1541(2) 0.45389(18) 0.0554(7) Uani 1 1 d . . . C8 C 0.1314(4) 0.1452(4) 0.4969(3) 0.1010(14) Uani 1 1 d . . . H8A H 0.1663 0.1488 0.5448 0.121 Uiso 1 1 calc R . . C9 C 0.0025(5) 0.1306(5) 0.4704(4) 0.138(2) Uani 1 1 d . . . H9A H -0.0477 0.1247 0.5008 0.165 Uiso 1 1 calc R . . C10 C -0.0493(4) 0.1250(4) 0.4025(4) 0.115(2) Uani 1 1 d . . . H10A H -0.1354 0.1154 0.3853 0.138 Uiso 1 1 calc R . . C11 C 0.0225(4) 0.1330(3) 0.3586(3) 0.1016(15) Uani 1 1 d . . . H11A H -0.0135 0.1277 0.3109 0.122 Uiso 1 1 calc R . . C12 C 0.1500(3) 0.1492(3) 0.3838(2) 0.0782(10) Uani 1 1 d . . . H12A H 0.1987 0.1569 0.3528 0.094 Uiso 1 1 calc R . . C13 C 0.4482(2) 0.3667(2) 0.34219(15) 0.0486(6) Uani 1 1 d . . . C14 C 0.3360(3) 0.4187(3) 0.33704(18) 0.0650(8) Uani 1 1 d . . . H14A H 0.3206 0.4479 0.3767 0.078 Uiso 1 1 calc R . . C15 C 0.2465(3) 0.4280(4) 0.2741(2) 0.0869(11) Uani 1 1 d . . . H15A H 0.1716 0.4632 0.2716 0.104 Uiso 1 1 calc R . . C16 C 0.2679(4) 0.3856(4) 0.2153(2) 0.0887(12) Uani 1 1 d . . . H16A H 0.2076 0.3920 0.1729 0.106 Uiso 1 1 calc R . . C17 C 0.3776(4) 0.3340(3) 0.21906(19) 0.0794(10) Uani 1 1 d . . . H17A H 0.3916 0.3042 0.1792 0.095 Uiso 1 1 calc R . . C18 C 0.4682(3) 0.3256(3) 0.28159(17) 0.0620(8) Uani 1 1 d . . . H18A H 0.5437 0.2919 0.2832 0.074 Uiso 1 1 calc R . . C19 C 0.8358(3) 0.5079(2) 0.39877(15) 0.0501(7) Uani 1 1 d . . . C20 C 0.8592(3) 0.6089(3) 0.3780(2) 0.0880(12) Uani 1 1 d . . . H20A H 0.7948 0.6590 0.3667 0.106 Uiso 1 1 calc R . . C21 C 0.9770(4) 0.6363(3) 0.3737(3) 0.1083(17) Uani 1 1 d . . . H21A H 0.9915 0.7046 0.3593 0.130 Uiso 1 1 calc R . . C22 C 1.0720(3) 0.5648(3) 0.3904(2) 0.0866(12) Uani 1 1 d . . . H22A H 1.1518 0.5844 0.3884 0.104 Uiso 1 1 calc R . . C23 C 1.0506(3) 0.4645(3) 0.41020(19) 0.0697(9) Uani 1 1 d . . . H23A H 1.1156 0.4150 0.4209 0.084 Uiso 1 1 calc R . . C24 C 0.9326(3) 0.4356(2) 0.41444(16) 0.0550(7) Uani 1 1 d . . . H24A H 0.9186 0.3666 0.4280 0.066 Uiso 1 1 calc R . . C25 C 0.7072(3) 0.4822(2) 0.40346(16) 0.0548(7) Uani 1 1 d . . . C26 C 0.6771(2) 0.3674(2) 0.41495(16) 0.0487(6) Uani 1 1 d . . . H26A H 0.7295 0.3440 0.4597 0.058 Uiso 1 1 calc R . . H26B H 0.6969 0.3234 0.3794 0.058 Uiso 1 1 calc R . . C27 C 0.5390(2) 0.3504(2) 0.41311(14) 0.0453(6) Uani 1 1 d . . . H27A H 0.5189 0.4051 0.4435 0.054 Uiso 1 1 calc R . . C28 C 0.5157(2) 0.2398(2) 0.44428(14) 0.0437(6) Uani 1 1 d . . . C29 C 0.3452(3) 0.1628(3) 0.48223(16) 0.0582(8) Uani 1 1 d . . . H29A H 0.3665 0.1772 0.5317 0.070 Uiso 1 1 calc R . . H29B H 0.3846 0.0961 0.4751 0.070 Uiso 1 1 calc R . . C30 C 0.5309(3) 0.1533(2) 0.39259(15) 0.0488(6) Uani 1 1 d . . . C31 C 0.4277(4) 0.0380(3) 0.3028(2) 0.0969(14) Uani 1 1 d . . . H31A H 0.3447 0.0127 0.2807 0.145 Uiso 1 1 calc R . . H31B H 0.4805 -0.0215 0.3221 0.145 Uiso 1 1 calc R . . H31C H 0.4610 0.0737 0.2692 0.145 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0998(3) 0.1414(5) 0.0656(3) 0.0194(2) -0.0102(2) -0.0409(3) O1 0.0504(11) 0.0649(13) 0.0807(15) -0.0252(11) 0.0215(10) -0.0182(10) O2 0.0482(12) 0.0735(14) 0.0790(15) -0.0202(12) 0.0261(10) 0.0013(10) O3 0.0605(14) 0.0509(13) 0.185(3) -0.0006(15) 0.0575(17) 0.0010(11) O4 0.0330(9) 0.0523(11) 0.0635(11) 0.0043(9) 0.0206(8) -0.0023(8) C1 0.0578(19) 0.078(2) 0.0583(19) 0.0104(17) 0.0057(15) -0.0284(18) C2 0.067(2) 0.076(2) 0.0572(19) -0.0105(17) 0.0203(16) -0.0244(18) C3 0.0493(16) 0.0570(17) 0.0611(18) -0.0052(14) 0.0196(14) -0.0058(13) C4 0.0348(13) 0.0468(15) 0.0571(16) -0.0012(13) 0.0172(12) -0.0085(11) C5 0.0506(16) 0.0546(17) 0.0640(18) 0.0032(14) 0.0165(14) 0.0002(13) C6 0.0550(18) 0.067(2) 0.076(2) 0.0164(18) 0.0099(16) -0.0009(15) C7 0.0381(14) 0.0519(16) 0.080(2) 0.0048(15) 0.0215(14) -0.0040(12) C8 0.059(2) 0.149(4) 0.107(3) 0.021(3) 0.043(2) -0.008(2) C9 0.060(3) 0.187(6) 0.185(6) 0.048(5) 0.065(4) -0.009(3) C10 0.039(2) 0.083(3) 0.213(6) 0.033(4) 0.017(3) -0.0042(19) C11 0.055(2) 0.087(3) 0.140(4) -0.002(3) -0.013(3) 0.011(2) C12 0.0471(18) 0.091(3) 0.091(3) 0.002(2) 0.0096(17) 0.0121(17) C13 0.0425(14) 0.0490(15) 0.0571(16) 0.0029(13) 0.0185(12) -0.0077(12) C14 0.0534(18) 0.074(2) 0.068(2) 0.0018(17) 0.0162(15) 0.0090(16) C15 0.062(2) 0.109(3) 0.083(3) 0.009(2) 0.0077(19) 0.018(2) C16 0.075(2) 0.112(3) 0.068(2) 0.007(2) -0.0008(19) -0.003(2) C17 0.085(3) 0.097(3) 0.057(2) -0.0022(19) 0.0201(18) -0.015(2) C18 0.0577(18) 0.071(2) 0.0621(19) 0.0007(16) 0.0241(15) -0.0054(15) C19 0.0445(14) 0.0477(15) 0.0614(17) -0.0083(13) 0.0197(13) -0.0109(12) C20 0.065(2) 0.055(2) 0.154(4) 0.017(2) 0.046(2) -0.0035(17) C21 0.081(3) 0.066(2) 0.195(5) 0.021(3) 0.067(3) -0.019(2) C22 0.058(2) 0.083(3) 0.132(3) -0.010(2) 0.049(2) -0.024(2) C23 0.0451(16) 0.077(2) 0.091(2) -0.0086(19) 0.0242(16) -0.0063(15) C24 0.0466(15) 0.0561(17) 0.0639(18) -0.0051(14) 0.0178(13) -0.0084(13) C25 0.0453(15) 0.0513(17) 0.072(2) -0.0061(14) 0.0236(14) -0.0066(13) C26 0.0374(13) 0.0483(15) 0.0626(17) -0.0018(13) 0.0175(12) -0.0069(12) C27 0.0384(13) 0.0443(14) 0.0569(16) -0.0037(12) 0.0192(12) -0.0041(11) C28 0.0316(12) 0.0465(15) 0.0553(16) -0.0027(12) 0.0158(11) -0.0038(11) C29 0.0432(15) 0.072(2) 0.0631(18) 0.0114(15) 0.0198(14) -0.0088(14) C30 0.0432(15) 0.0461(15) 0.0591(17) -0.0024(13) 0.0171(13) -0.0033(12) C31 0.091(3) 0.096(3) 0.108(3) -0.057(3) 0.034(2) -0.031(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.895(3) . ? O1 C30 1.317(3) . ? O1 C31 1.445(4) . ? O2 C30 1.200(3) . ? O3 C25 1.207(4) . ? O4 C28 1.422(3) . ? O4 C29 1.429(3) . ? C1 C6 1.361(5) . ? C1 C2 1.375(5) . ? C2 C3 1.377(4) . ? C2 H2A 0.9300 . ? C3 C4 1.392(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 C28 1.526(4) . ? C5 C6 1.388(5) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.349(5) . ? C7 C12 1.371(5) . ? C7 C29 1.498(4) . ? C8 C9 1.395(6) . ? C8 H8A 0.9300 . ? C9 C10 1.326(8) . ? C9 H9A 0.9300 . ? C10 C11 1.339(7) . ? C10 H10A 0.9300 . ? C11 C12 1.380(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.382(4) . ? C13 C18 1.388(4) . ? C13 C27 1.514(4) . ? C14 C15 1.381(5) . ? C14 H14A 0.9300 . ? C15 C16 1.367(6) . ? C15 H15A 0.9300 . ? C16 C17 1.362(6) . ? C16 H16A 0.9300 . ? C17 C18 1.379(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C24 1.374(4) . ? C19 C20 1.377(4) . ? C19 C25 1.489(4) . ? C20 C21 1.374(5) . ? C20 H20A 0.9300 . ? C21 C22 1.353(6) . ? C21 H21A 0.9300 . ? C22 C23 1.356(5) . ? C22 H22A 0.9300 . ? C23 C24 1.381(4) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C26 1.508(4) . ? C26 C27 1.535(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.568(4) . ? C27 H27A 0.9800 . ? C28 C30 1.537(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C30 O1 C31 116.1(2) . . ? C28 O4 C29 116.1(2) . . ? C6 C1 C2 121.2(3) . . ? C6 C1 Br1 118.7(3) . . ? C2 C1 Br1 120.1(3) . . ? C1 C2 C3 119.1(3) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 117.9(3) . . ? C5 C4 C28 124.5(2) . . ? C3 C4 C28 117.6(2) . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 119.5(3) . . ? C1 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C8 C7 C12 117.6(3) . . ? C8 C7 C29 120.8(3) . . ? C12 C7 C29 121.6(3) . . ? C7 C8 C9 120.6(5) . . ? C7 C8 H8A 119.7 . . ? C9 C8 H8A 119.7 . . ? C10 C9 C8 120.8(5) . . ? C10 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C10 C11 C12 120.2(5) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C7 C12 C11 120.9(4) . . ? C7 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C14 C13 C18 117.5(3) . . ? C14 C13 C27 119.3(3) . . ? C18 C13 C27 123.0(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C16 C15 C14 120.1(4) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C18 120.5(4) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C18 C13 120.9(3) . . ? C17 C18 H18A 119.6 . . ? C13 C18 H18A 119.6 . . ? C24 C19 C20 118.3(3) . . ? C24 C19 C25 123.0(3) . . ? C20 C19 C25 118.6(3) . . ? C21 C20 C19 120.5(4) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C22 C21 C20 120.6(4) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? C21 C22 C23 119.9(3) . . ? C21 C22 H22A 120.1 . . ? C23 C22 H22A 120.1 . . ? C22 C23 C24 120.2(3) . . ? C22 C23 H23A 119.9 . . ? C24 C23 H23A 119.9 . . ? C19 C24 C23 120.5(3) . . ? C19 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? O3 C25 C19 120.5(3) . . ? O3 C25 C26 121.4(2) . . ? C19 C25 C26 118.1(2) . . ? C25 C26 C27 112.9(2) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C13 C27 C26 114.2(2) . . ? C13 C27 C28 110.6(2) . . ? C26 C27 C28 112.5(2) . . ? C13 C27 H27A 106.3 . . ? C26 C27 H27A 106.3 . . ? C28 C27 H27A 106.3 . . ? O4 C28 C4 110.0(2) . . ? O4 C28 C30 111.4(2) . . ? C4 C28 C30 112.9(2) . . ? O4 C28 C27 103.06(19) . . ? C4 C28 C27 111.8(2) . . ? C30 C28 C27 107.2(2) . . ? O4 C29 C7 108.8(2) . . ? O4 C29 H29A 109.9 . . ? C7 C29 H29A 109.9 . . ? O4 C29 H29B 109.9 . . ? C7 C29 H29B 109.9 . . ? H29A C29 H29B 108.3 . . ? O2 C30 O1 124.2(3) . . ? O2 C30 C28 123.1(2) . . ? O1 C30 C28 112.7(2) . . ? O1 C31 H31A 109.5 . . ? O1 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O1 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.0(5) . . . . ? Br1 C1 C2 C3 -177.9(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C2 C3 C4 C28 177.2(2) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C28 C4 C5 C6 -177.2(3) . . . . ? C2 C1 C6 C5 -1.1(5) . . . . ? Br1 C1 C6 C5 177.8(2) . . . . ? C4 C5 C6 C1 0.1(5) . . . . ? C12 C7 C8 C9 0.6(7) . . . . ? C29 C7 C8 C9 -176.1(4) . . . . ? C7 C8 C9 C10 0.1(9) . . . . ? C8 C9 C10 C11 0.2(9) . . . . ? C9 C10 C11 C12 -1.2(8) . . . . ? C8 C7 C12 C11 -1.6(6) . . . . ? C29 C7 C12 C11 175.0(3) . . . . ? C10 C11 C12 C7 2.0(6) . . . . ? C18 C13 C14 C15 0.9(5) . . . . ? C27 C13 C14 C15 -175.0(3) . . . . ? C13 C14 C15 C16 -0.1(6) . . . . ? C14 C15 C16 C17 0.1(7) . . . . ? C15 C16 C17 C18 -0.9(6) . . . . ? C16 C17 C18 C13 1.8(5) . . . . ? C14 C13 C18 C17 -1.7(5) . . . . ? C27 C13 C18 C17 174.0(3) . . . . ? C24 C19 C20 C21 -0.6(6) . . . . ? C25 C19 C20 C21 179.2(4) . . . . ? C19 C20 C21 C22 -0.5(8) . . . . ? C20 C21 C22 C23 1.3(8) . . . . ? C21 C22 C23 C24 -1.1(6) . . . . ? C20 C19 C24 C23 0.9(5) . . . . ? C25 C19 C24 C23 -178.9(3) . . . . ? C22 C23 C24 C19 -0.1(5) . . . . ? C24 C19 C25 O3 170.0(3) . . . . ? C20 C19 C25 O3 -9.8(5) . . . . ? C24 C19 C25 C26 -9.9(4) . . . . ? C20 C19 C25 C26 170.3(3) . . . . ? O3 C25 C26 C27 4.6(4) . . . . ? C19 C25 C26 C27 -175.5(2) . . . . ? C14 C13 C27 C26 -139.7(3) . . . . ? C18 C13 C27 C26 44.6(4) . . . . ? C14 C13 C27 C28 92.2(3) . . . . ? C18 C13 C27 C28 -83.5(3) . . . . ? C25 C26 C27 C13 68.2(3) . . . . ? C25 C26 C27 C28 -164.6(2) . . . . ? C29 O4 C28 C4 -52.8(3) . . . . ? C29 O4 C28 C30 73.3(3) . . . . ? C29 O4 C28 C27 -172.2(2) . . . . ? C5 C4 C28 O4 132.2(3) . . . . ? C3 C4 C28 O4 -45.8(3) . . . . ? C5 C4 C28 C30 7.1(3) . . . . ? C3 C4 C28 C30 -171.0(2) . . . . ? C5 C4 C28 C27 -113.9(3) . . . . ? C3 C4 C28 C27 68.1(3) . . . . ? C13 C27 C28 O4 -59.4(3) . . . . ? C26 C27 C28 O4 171.5(2) . . . . ? C13 C27 C28 C4 -177.6(2) . . . . ? C26 C27 C28 C4 53.4(3) . . . . ? C13 C27 C28 C30 58.1(3) . . . . ? C26 C27 C28 C30 -70.9(3) . . . . ? C28 O4 C29 C7 -154.1(2) . . . . ? C8 C7 C29 O4 -133.3(4) . . . . ? C12 C7 C29 O4 50.1(4) . . . . ? C31 O1 C30 O2 -3.1(5) . . . . ? C31 O1 C30 C28 173.6(3) . . . . ? O4 C28 C30 O2 -177.7(3) . . . . ? C4 C28 C30 O2 -53.3(4) . . . . ? C27 C28 C30 O2 70.3(3) . . . . ? O4 C28 C30 O1 5.6(3) . . . . ? C4 C28 C30 O1 130.0(2) . . . . ? C27 C28 C30 O1 -106.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.646 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.044