# 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 'Magnus Rueping' _publ_contact_author_email Magnus.Rueping@rwth-aachen.de _publ_author_name M.Rueping data_mr49 _database_code_depnum_ccdc_archive 'CCDC 876877' #TrackingRef '- mr49(Fig2).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 O4' _chemical_formula_sum 'C18 H20 O4' _chemical_formula_weight 300.34 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.633(2) _cell_length_b 8.046(2) _cell_length_c 14.859(5) _cell_angle_alpha 77.08(2) _cell_angle_beta 88.83(2) _cell_angle_gamma 62.32(2) _cell_volume 784.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3007 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 26.0 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min . _exptl_absorpt_correction_T_max . _exptl_absorpt_process_details . _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10767 _diffrn_reflns_av_R_equivalents 0.2943 _diffrn_reflns_av_sigmaI/netI 0.2007 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2756 _reflns_number_gt 1055 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.1224P)^2^] 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 2756 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2177 _refine_ls_R_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.3108 _refine_ls_wR_factor_gt 0.2413 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 0.4850(6) 0.7112(6) 0.3447(4) 0.0826(15) Uani 1 1 d . A . O2 O 0.4430(13) 0.9506(15) 0.2229(7) 0.084(4) Uani 0.506(12) 1 d P A 1 H2 H 0.4224 1.0035 0.2675 0.126 Uiso 0.506(12) 1 calc PR A 1 O2' O 0.2245(11) 0.8898(14) 0.2295(8) 0.090(4) Uani 0.494(12) 1 d P A 2 H2' H 0.1811 0.9950 0.2452 0.135 Uiso 0.494(12) 1 calc PR A 2 O3 O 0.6252(5) 0.6015(6) 0.5213(3) 0.0773(15) Uani 1 1 d . . . O4 O 1.0993(6) 0.2220(6) 0.2848(3) 0.0823(15) Uani 1 1 d . A . C2 C 0.4180(9) 0.7943(11) 0.2468(6) 0.084(2) Uani 1 1 d . . . H2A H 0.2709 0.8436 0.2424 0.100 Uiso 0.506(12) 1 calc PR A 1 H2B H 0.4700 0.8881 0.2241 0.100 Uiso 0.494(12) 1 calc PR A 2 C3 C 0.4984(8) 0.6435(10) 0.1891(6) 0.082(2) Uani 1 1 d . A . H3 H 0.4587 0.7144 0.1223 0.099 Uiso 1 1 calc R . . C4 C 0.7307(8) 0.5407(8) 0.2041(5) 0.0706(19) Uani 1 1 d . . . H4 H 0.7813 0.4233 0.1786 0.085 Uiso 1 1 calc R A . C5 C 0.7915(8) 0.4731(8) 0.3057(5) 0.0657(18) Uani 1 1 d . A . C6 C 0.6737(8) 0.5606(8) 0.3690(5) 0.0671(18) Uani 1 1 d . . . C7 C 0.7288(8) 0.5061(8) 0.4681(5) 0.0630(17) Uani 1 1 d . A . C8 C 0.9899(8) 0.2998(8) 0.3428(5) 0.0641(17) Uani 1 1 d . . . C9 C 0.9239(7) 0.3257(7) 0.5054(5) 0.0594(17) Uani 1 1 d . . . C10 C 1.0456(7) 0.2264(8) 0.4420(5) 0.0632(18) Uani 1 1 d . A . C11 C 1.2235(7) 0.0575(8) 0.4785(5) 0.0655(18) Uani 1 1 d . . . H11 H 1.3086 -0.0111 0.4373 0.079 Uiso 1 1 calc R A . C12 C 1.2762(8) -0.0094(8) 0.5702(6) 0.0683(19) Uani 1 1 d . A . H12 H 1.3963 -0.1256 0.5925 0.082 Uiso 1 1 calc R . . C13 C 1.1568(8) 0.0893(8) 0.6345(6) 0.074(2) Uani 1 1 d . . . H13 H 1.1959 0.0432 0.6993 0.088 Uiso 1 1 calc R A . C14 C 0.9772(8) 0.2591(8) 0.5984(5) 0.0678(18) Uani 1 1 d . A . H14 H 0.8925 0.3278 0.6397 0.081 Uiso 1 1 calc R . . C31 C 0.4142(10) 0.5063(11) 0.2089(7) 0.097(3) Uani 1 1 d . . . H31A H 0.2682 0.5825 0.2081 0.117 Uiso 1 1 calc R A . H31B H 0.4659 0.4242 0.2725 0.117 Uiso 1 1 calc R . . C32 C 0.4577(13) 0.3732(13) 0.1424(8) 0.115(3) Uani 1 1 d . A . H32A H 0.4006 0.2859 0.1633 0.173 Uiso 1 1 calc R . . H32B H 0.6018 0.2970 0.1420 0.173 Uiso 1 1 calc R . . H32C H 0.3985 0.4517 0.0797 0.173 Uiso 1 1 calc R . . C41 C 0.8260(9) 0.6614(10) 0.1559(6) 0.085(2) Uani 1 1 d . A . H41A H 0.9707 0.5874 0.1746 0.102 Uiso 1 1 calc R . . H41B H 0.7740 0.7800 0.1793 0.102 Uiso 1 1 calc R . . C42 C 0.7944(12) 0.7231(14) 0.0478(7) 0.109(3) Uani 1 1 d . . . H42A H 0.8410 0.6059 0.0236 0.130 Uiso 1 1 calc R A . H42B H 0.6505 0.8043 0.0283 0.130 Uiso 1 1 calc R . . C43 C 0.8989(14) 0.8309(15) 0.0063(8) 0.132(4) Uani 1 1 d . A . H43A H 0.8747 0.8637 -0.0614 0.199 Uiso 1 1 calc R . . H43B H 1.0419 0.7511 0.0247 0.199 Uiso 1 1 calc R . . H43C H 0.8500 0.9499 0.0280 0.199 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 0.051(2) 0.059(2) 0.102(4) -0.031(3) -0.010(2) 0.0092(18) O2 0.060(5) 0.088(7) 0.081(8) -0.025(5) 0.024(5) -0.014(5) O2' 0.043(5) 0.086(7) 0.108(9) -0.033(6) -0.004(4) 0.001(4) O3 0.047(2) 0.059(2) 0.101(4) -0.036(2) 0.004(2) 0.0031(18) O4 0.063(3) 0.066(3) 0.087(4) -0.027(3) 0.019(2) -0.002(2) C2 0.046(3) 0.070(4) 0.116(7) -0.026(5) -0.005(4) -0.010(3) C3 0.048(3) 0.085(4) 0.108(6) -0.034(4) 0.001(4) -0.021(3) C4 0.053(3) 0.050(3) 0.090(6) -0.016(3) 0.000(3) -0.009(3) C5 0.045(3) 0.049(3) 0.088(5) -0.018(3) 0.001(3) -0.008(2) C6 0.044(3) 0.051(3) 0.088(5) -0.023(3) -0.008(3) -0.004(3) C7 0.044(3) 0.042(3) 0.091(5) -0.021(3) 0.004(3) -0.008(2) C8 0.055(3) 0.048(3) 0.079(5) -0.024(3) 0.010(3) -0.013(3) C9 0.041(3) 0.041(3) 0.084(5) -0.021(3) 0.000(3) -0.007(2) C10 0.036(3) 0.051(3) 0.092(6) -0.029(3) 0.005(3) -0.007(2) C11 0.032(3) 0.051(3) 0.095(6) -0.019(3) 0.002(3) -0.005(2) C12 0.045(3) 0.045(3) 0.096(6) -0.017(3) -0.001(3) -0.005(2) C13 0.055(3) 0.056(3) 0.096(6) -0.027(4) -0.004(3) -0.011(3) C14 0.054(3) 0.054(3) 0.080(6) -0.024(3) 0.002(3) -0.010(3) C31 0.064(4) 0.098(5) 0.133(8) -0.043(5) -0.005(4) -0.034(4) C32 0.105(6) 0.111(6) 0.152(9) -0.067(6) 0.007(6) -0.054(5) C41 0.054(3) 0.083(5) 0.109(7) -0.039(5) -0.001(4) -0.018(3) C42 0.085(5) 0.127(7) 0.105(8) -0.026(6) 0.009(5) -0.044(5) C43 0.103(6) 0.140(8) 0.140(9) -0.002(7) 0.008(6) -0.059(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.370(6) . ? O1 C2 1.450(9) . ? O2 C2 1.328(12) . ? O2 H2 0.8400 . ? O2' C2 1.308(9) . ? O2' H2' 0.8400 . ? O3 C7 1.234(7) . ? O4 C8 1.248(7) . ? C2 C3 1.529(10) . ? C2 H2A 1.0000 . ? C2 H2B 1.0000 . ? C3 C31 1.492(10) . ? C3 C4 1.565(8) . ? C3 H3 1.0000 . ? C4 C5 1.489(9) . ? C4 C41 1.519(10) . ? C4 H4 1.0000 . ? C5 C6 1.364(9) . ? C5 C8 1.507(8) . ? C6 C7 1.451(10) . ? C7 C9 1.516(7) . ? C8 C10 1.451(9) . ? C9 C14 1.361(9) . ? C9 C10 1.414(8) . ? C10 C11 1.404(7) . ? C11 C12 1.342(9) . ? C11 H11 0.9500 . ? C12 C13 1.416(9) . ? C12 H12 0.9500 . ? C13 C14 1.413(8) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C31 C32 1.537(11) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 C42 1.559(11) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.467(12) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 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 C6 O1 C2 118.1(5) . . ? C2 O2 H2 109.5 . . ? C2 O2' H2' 109.5 . . ? O2' C2 O2 94.7(8) . . ? O2' C2 O1 113.6(8) . . ? O2 C2 O1 106.8(8) . . ? O2' C2 C3 108.1(8) . . ? O2 C2 C3 119.6(8) . . ? O1 C2 C3 112.8(6) . . ? O2' C2 H2A 11.7 . . ? O2 C2 H2A 105.5 . . ? O1 C2 H2A 105.5 . . ? C3 C2 H2A 105.5 . . ? O2' C2 H2B 107.3 . . ? O2 C2 H2B 14.8 . . ? O1 C2 H2B 107.3 . . ? C3 C2 H2B 107.3 . . ? H2A C2 H2B 118.6 . . ? C31 C3 C2 112.9(7) . . ? C31 C3 C4 113.4(6) . . ? C2 C3 C4 107.9(6) . . ? C31 C3 H3 107.5 . . ? C2 C3 H3 107.5 . . ? C4 C3 H3 107.5 . . ? C5 C4 C41 111.2(6) . . ? C5 C4 C3 108.3(6) . . ? C41 C4 C3 115.0(6) . . ? C5 C4 H4 107.3 . . ? C41 C4 H4 107.3 . . ? C3 C4 H4 107.3 . . ? C6 C5 C4 122.9(5) . . ? C6 C5 C8 117.1(7) . . ? C4 C5 C8 120.0(5) . . ? C5 C6 O1 122.7(7) . . ? C5 C6 C7 125.1(5) . . ? O1 C6 C7 112.2(5) . . ? O3 C7 C6 122.6(5) . . ? O3 C7 C9 120.0(7) . . ? C6 C7 C9 117.3(5) . . ? O4 C8 C10 122.5(5) . . ? O4 C8 C5 117.1(6) . . ? C10 C8 C5 120.4(5) . . ? C14 C9 C10 121.1(5) . . ? C14 C9 C7 120.1(6) . . ? C10 C9 C7 118.8(6) . . ? C11 C10 C9 117.6(7) . . ? C11 C10 C8 121.4(6) . . ? C9 C10 C8 120.9(5) . . ? C12 C11 C10 121.5(6) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 121.6(5) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 117.3(7) . . ? C14 C13 H13 121.3 . . ? C12 C13 H13 121.3 . . ? C9 C14 C13 120.9(6) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C3 C31 C32 116.3(8) . . ? C3 C31 H31A 108.2 . . ? C32 C31 H31A 108.2 . . ? C3 C31 H31B 108.2 . . ? C32 C31 H31B 108.2 . . ? H31A C31 H31B 107.4 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C4 C41 C42 116.8(7) . . ? C4 C41 H41A 108.1 . . ? C42 C41 H41A 108.1 . . ? C4 C41 H41B 108.1 . . ? C42 C41 H41B 108.1 . . ? H41A C41 H41B 107.3 . . ? C43 C42 C41 113.5(9) . . ? C43 C42 H42A 108.9 . . ? C41 C42 H42A 108.9 . . ? C43 C42 H42B 108.9 . . ? C41 C42 H42B 108.9 . . ? H42A C42 H42B 107.7 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 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 O1 C2 O2' 159.2(8) . . . . ? C6 O1 C2 O2 -97.7(7) . . . . ? C6 O1 C2 C3 35.7(8) . . . . ? O2' C2 C3 C31 -58.3(10) . . . . ? O2 C2 C3 C31 -164.9(8) . . . . ? O1 C2 C3 C31 68.2(8) . . . . ? O2' C2 C3 C4 175.7(9) . . . . ? O2 C2 C3 C4 69.1(10) . . . . ? O1 C2 C3 C4 -57.8(8) . . . . ? C31 C3 C4 C5 -74.3(8) . . . . ? C2 C3 C4 C5 51.4(8) . . . . ? C31 C3 C4 C41 160.6(7) . . . . ? C2 C3 C4 C41 -73.6(8) . . . . ? C41 C4 C5 C6 100.1(7) . . . . ? C3 C4 C5 C6 -27.1(9) . . . . ? C41 C4 C5 C8 -80.4(7) . . . . ? C3 C4 C5 C8 152.3(5) . . . . ? C4 C5 C6 O1 3.9(10) . . . . ? C8 C5 C6 O1 -175.6(6) . . . . ? C4 C5 C6 C7 -177.2(6) . . . . ? C8 C5 C6 C7 3.4(9) . . . . ? C2 O1 C6 C5 -7.4(9) . . . . ? C2 O1 C6 C7 173.5(6) . . . . ? C5 C6 C7 O3 172.7(6) . . . . ? O1 C6 C7 O3 -8.3(9) . . . . ? C5 C6 C7 C9 -6.5(9) . . . . ? O1 C6 C7 C9 172.6(5) . . . . ? C6 C5 C8 O4 -178.6(6) . . . . ? C4 C5 C8 O4 1.9(9) . . . . ? C6 C5 C8 C10 2.9(9) . . . . ? C4 C5 C8 C10 -176.5(6) . . . . ? O3 C7 C9 C14 5.6(9) . . . . ? C6 C7 C9 C14 -175.3(6) . . . . ? O3 C7 C9 C10 -176.0(6) . . . . ? C6 C7 C9 C10 3.2(8) . . . . ? C14 C9 C10 C11 -0.3(9) . . . . ? C7 C9 C10 C11 -178.7(5) . . . . ? C14 C9 C10 C8 -178.9(6) . . . . ? C7 C9 C10 C8 2.7(8) . . . . ? O4 C8 C10 C11 -2.8(10) . . . . ? C5 C8 C10 C11 175.6(5) . . . . ? O4 C8 C10 C9 175.8(6) . . . . ? C5 C8 C10 C9 -5.9(9) . . . . ? C9 C10 C11 C12 0.7(9) . . . . ? C8 C10 C11 C12 179.3(6) . . . . ? C10 C11 C12 C13 -1.3(10) . . . . ? C11 C12 C13 C14 1.4(9) . . . . ? C10 C9 C14 C13 0.5(9) . . . . ? C7 C9 C14 C13 178.9(5) . . . . ? C12 C13 C14 C9 -1.0(9) . . . . ? C2 C3 C31 C32 169.6(7) . . . . ? C4 C3 C31 C32 -67.3(9) . . . . ? C5 C4 C41 C42 173.5(6) . . . . ? C3 C4 C41 C42 -63.0(8) . . . . ? C4 C41 C42 C43 -177.1(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O4 0.84 2.32 2.824(8) 118.8 1_465 O2' H2' O4 0.84 1.86 2.703(11) 176.5 1_465 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.252 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.061 # Attachment '- mr50(Fig3).cif' data_mr50 _database_code_depnum_ccdc_archive 'CCDC 876878' #TrackingRef '- mr50(Fig3).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 Br O4' _chemical_formula_sum 'C19 H21 Br O4' _chemical_formula_weight 393.27 _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' 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 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 10.7772(8) _cell_length_b 6.5073(5) _cell_length_c 25.4062(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.353(6) _cell_angle_gamma 90.00 _cell_volume 1781.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13729 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.3 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5052 _exptl_absorpt_correction_T_max 0.7519 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14228 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.0733 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.97 _reflns_number_total 3813 _reflns_number_gt 3440 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0912P)^2^] 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 0.0180(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(12) _refine_ls_number_reflns 3813 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.32268(4) 0.90082(9) 0.035134(15) 0.0567(2) Uani 1 1 d . . . O1 O 0.7761(2) 0.2926(4) 0.27471(10) 0.0364(6) Uani 1 1 d . . . O2 O 0.7571(2) 0.4630(4) 0.19487(10) 0.0370(6) Uani 1 1 d . . . O3 O 0.6676(3) 0.1697(4) 0.16566(12) 0.0439(7) Uani 1 1 d . . . O4 O 0.8810(3) 0.9244(5) 0.35656(12) 0.0502(7) Uani 1 1 d . . . C1 C 0.8402(3) 0.3449(6) 0.22786(14) 0.0364(8) Uani 1 1 d . . . H1 H 0.8642 0.2162 0.2090 0.044 Uiso 1 1 calc R . . C2 C 0.9543(3) 0.4741(6) 0.23731(15) 0.0377(8) Uani 1 1 d . . . H2 H 0.9899 0.5128 0.2024 0.045 Uiso 1 1 calc R . . C3 C 0.9169(3) 0.6700(6) 0.26591(16) 0.0385(8) Uani 1 1 d . . . H3A H 0.9920 0.7433 0.2784 0.046 Uiso 1 1 calc R . . H3B H 0.8711 0.7617 0.2415 0.046 Uiso 1 1 calc R . . C4 C 0.8366(3) 0.6161(6) 0.31177(16) 0.0368(8) Uani 1 1 d . . . C5 C 0.7753(3) 0.4340(6) 0.31420(14) 0.0346(7) Uani 1 1 d . . . C6 C 0.7002(4) 0.3622(6) 0.35923(15) 0.0409(9) Uani 1 1 d . . . H6A H 0.7126 0.2124 0.3636 0.049 Uiso 1 1 calc R . . H6B H 0.6113 0.3855 0.3511 0.049 Uiso 1 1 calc R . . C7 C 0.7328(4) 0.4706(7) 0.41149(15) 0.0421(9) Uani 1 1 d . . . C8 C 0.7369(4) 0.7033(7) 0.40020(16) 0.0436(9) Uani 1 1 d . . . H8A H 0.6522 0.7511 0.3911 0.052 Uiso 1 1 calc R . . H8B H 0.7635 0.7762 0.4326 0.052 Uiso 1 1 calc R . . C9 C 0.8244(3) 0.7600(6) 0.35565(16) 0.0383(8) Uani 1 1 d . . . C10 C 0.6720(3) 0.3564(6) 0.16659(14) 0.0366(8) Uani 1 1 d . . . C11 C 0.5875(4) 0.4948(6) 0.13635(14) 0.0372(8) Uani 1 1 d . . . C12 C 0.4790(3) 0.4101(9) 0.11459(15) 0.0442(8) Uani 1 1 d . . . H12 H 0.4598 0.2697 0.1206 0.053 Uiso 1 1 calc R . . C13 C 0.4011(4) 0.5280(7) 0.08484(17) 0.0474(10) Uani 1 1 d . . . H13 H 0.3274 0.4709 0.0703 0.057 Uiso 1 1 calc R . . C14 C 0.4310(4) 0.7327(7) 0.07613(15) 0.0423(9) Uani 1 1 d . . . C15 C 0.5365(4) 0.8195(7) 0.09717(16) 0.0438(9) Uani 1 1 d . . . H15 H 0.5559 0.9595 0.0905 0.053 Uiso 1 1 calc R . . C16 C 0.6144(4) 0.6997(6) 0.12830(15) 0.0393(8) Uani 1 1 d . . . H16 H 0.6862 0.7588 0.1440 0.047 Uiso 1 1 calc R . . C17 C 1.0518(4) 0.3484(7) 0.26780(16) 0.0450(9) Uani 1 1 d . . . H17A H 1.1257 0.4330 0.2739 0.067 Uiso 1 1 calc R . . H17B H 1.0744 0.2267 0.2473 0.067 Uiso 1 1 calc R . . H17C H 1.0174 0.3055 0.3017 0.067 Uiso 1 1 calc R . . C18 C 0.6333(4) 0.4229(10) 0.45235(16) 0.0567(11) Uani 1 1 d . . . H18A H 0.6317 0.2747 0.4592 0.085 Uiso 1 1 calc R . . H18B H 0.5521 0.4670 0.4389 0.085 Uiso 1 1 calc R . . H18C H 0.6523 0.4964 0.4851 0.085 Uiso 1 1 calc R . . C19 C 0.8599(4) 0.3981(9) 0.43202(15) 0.0507(9) Uani 1 1 d . . . H19A H 0.9236 0.4290 0.4058 0.076 Uiso 1 1 calc R . . H19B H 0.8574 0.2496 0.4383 0.076 Uiso 1 1 calc R . . H19C H 0.8797 0.4694 0.4650 0.076 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 0.0545(3) 0.0699(3) 0.0455(2) 0.0014(2) -0.01119(16) 0.0184(2) O1 0.0399(13) 0.0342(13) 0.0351(13) -0.0044(10) -0.0005(10) -0.0045(10) O2 0.0371(12) 0.0337(13) 0.0401(13) -0.0018(9) -0.0111(11) -0.0025(9) O3 0.0439(14) 0.0294(14) 0.0583(17) -0.0035(12) -0.0089(13) -0.0032(10) O4 0.0512(15) 0.0369(15) 0.0625(16) -0.0100(15) -0.0072(12) 0.0023(14) C1 0.0390(18) 0.0348(19) 0.0352(16) -0.0004(13) -0.0035(14) 0.0026(13) C2 0.0345(17) 0.0426(19) 0.0361(17) -0.0012(14) -0.0003(14) -0.0008(14) C3 0.0325(17) 0.0354(19) 0.047(2) -0.0005(16) -0.0069(15) -0.0052(14) C4 0.0312(16) 0.0340(17) 0.045(2) -0.0032(14) -0.0068(15) 0.0038(14) C5 0.0338(15) 0.0300(19) 0.0398(16) -0.0054(14) -0.0064(13) 0.0041(13) C6 0.0399(17) 0.044(2) 0.0390(17) -0.0011(16) -0.0013(14) -0.0031(16) C7 0.044(2) 0.047(2) 0.0348(17) 0.0000(15) -0.0033(15) 0.0069(16) C8 0.0426(19) 0.045(2) 0.044(2) -0.0076(17) -0.0023(16) 0.0125(16) C9 0.0381(18) 0.0317(17) 0.045(2) -0.0060(15) -0.0109(16) 0.0083(14) C10 0.0347(16) 0.040(2) 0.0354(16) -0.0009(14) -0.0009(13) -0.0027(14) C11 0.0387(18) 0.0370(18) 0.0357(17) -0.0035(14) -0.0039(15) 0.0011(14) C12 0.0415(17) 0.0444(19) 0.0467(17) -0.003(2) -0.0081(14) -0.006(2) C13 0.040(2) 0.052(2) 0.050(2) -0.0071(19) -0.0087(17) -0.0046(17) C14 0.041(2) 0.051(2) 0.0345(18) -0.0031(16) -0.0037(15) 0.0067(17) C15 0.052(2) 0.042(2) 0.0373(19) -0.0011(15) -0.0050(16) 0.0045(17) C16 0.0392(19) 0.0394(19) 0.0393(18) -0.0028(15) -0.0064(15) -0.0011(15) C17 0.0369(18) 0.054(2) 0.044(2) -0.0012(17) -0.0070(15) 0.0070(16) C18 0.058(2) 0.072(3) 0.0401(18) 0.003(3) 0.0052(17) 0.004(3) C19 0.054(2) 0.053(2) 0.0451(18) -0.001(3) -0.0132(16) 0.007(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 C14 1.905(4) . ? O1 C5 1.362(4) . ? O1 C1 1.421(5) . ? O2 C10 1.353(4) . ? O2 C1 1.444(4) . ? O3 C10 1.216(5) . ? O4 C9 1.232(5) . ? C1 C2 1.508(5) . ? C1 H1 1.0000 . ? C2 C3 1.523(5) . ? C2 C17 1.537(5) . ? C2 H2 1.0000 . ? C3 C4 1.498(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.358(5) . ? C4 C9 1.463(5) . ? C5 C6 1.481(5) . ? C6 C7 1.542(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C18 1.529(6) . ? C7 C19 1.537(5) . ? C7 C8 1.542(6) . ? C8 C9 1.522(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.491(5) . ? C11 C16 1.380(6) . ? C11 C12 1.403(5) . ? C12 C13 1.363(7) . ? C12 H12 0.9500 . ? C13 C14 1.388(7) . ? C13 H13 0.9500 . ? C14 C15 1.375(6) . ? C15 C16 1.389(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C5 O1 C1 117.5(3) . . ? C10 O2 C1 116.8(3) . . ? O1 C1 O2 108.1(3) . . ? O1 C1 C2 113.6(3) . . ? O2 C1 C2 107.3(3) . . ? O1 C1 H1 109.2 . . ? O2 C1 H1 109.2 . . ? C2 C1 H1 109.2 . . ? C1 C2 C3 109.0(3) . . ? C1 C2 C17 109.8(3) . . ? C3 C2 C17 112.7(3) . . ? C1 C2 H2 108.4 . . ? C3 C2 H2 108.4 . . ? C17 C2 H2 108.4 . . ? C4 C3 C2 109.3(3) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? C5 C4 C9 118.5(4) . . ? C5 C4 C3 121.6(3) . . ? C9 C4 C3 119.9(3) . . ? C4 C5 O1 123.4(3) . . ? C4 C5 C6 125.4(3) . . ? O1 C5 C6 111.2(3) . . ? C5 C6 C7 113.5(3) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C18 C7 C19 109.6(3) . . ? C18 C7 C8 110.3(4) . . ? C19 C7 C8 109.8(4) . . ? C18 C7 C6 109.5(3) . . ? C19 C7 C6 110.5(3) . . ? C8 C7 C6 107.2(3) . . ? C9 C8 C7 113.2(3) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? O4 C9 C4 121.6(4) . . ? O4 C9 C8 120.4(4) . . ? C4 C9 C8 118.1(4) . . ? O3 C10 O2 123.3(3) . . ? O3 C10 C11 124.8(3) . . ? O2 C10 C11 111.9(3) . . ? C16 C11 C12 119.8(4) . . ? C16 C11 C10 122.1(3) . . ? C12 C11 C10 118.1(4) . . ? C13 C12 C11 120.4(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C15 C14 C13 121.6(4) . . ? C15 C14 Br1 118.6(3) . . ? C13 C14 Br1 119.8(3) . . ? C14 C15 C16 119.1(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 120.0(4) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 C18 H18A 109.5 . . ? C7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 C19 H19A 109.5 . . ? C7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C5 O1 C1 O2 -84.4(3) . . . . ? C5 O1 C1 C2 34.6(4) . . . . ? C10 O2 C1 O1 -79.8(4) . . . . ? C10 O2 C1 C2 157.3(3) . . . . ? O1 C1 C2 C3 -57.9(4) . . . . ? O2 C1 C2 C3 61.6(4) . . . . ? O1 C1 C2 C17 66.0(4) . . . . ? O2 C1 C2 C17 -174.5(3) . . . . ? C1 C2 C3 C4 48.7(4) . . . . ? C17 C2 C3 C4 -73.5(4) . . . . ? C2 C3 C4 C5 -20.8(5) . . . . ? C2 C3 C4 C9 158.3(3) . . . . ? C9 C4 C5 O1 177.3(3) . . . . ? C3 C4 C5 O1 -3.7(5) . . . . ? C9 C4 C5 C6 -3.0(5) . . . . ? C3 C4 C5 C6 176.0(3) . . . . ? C1 O1 C5 C4 -3.0(5) . . . . ? C1 O1 C5 C6 177.2(3) . . . . ? C4 C5 C6 C7 -21.0(5) . . . . ? O1 C5 C6 C7 158.7(3) . . . . ? C5 C6 C7 C18 167.5(4) . . . . ? C5 C6 C7 C19 -71.7(5) . . . . ? C5 C6 C7 C8 47.9(4) . . . . ? C18 C7 C8 C9 -173.9(3) . . . . ? C19 C7 C8 C9 65.3(4) . . . . ? C6 C7 C8 C9 -54.7(4) . . . . ? C5 C4 C9 O4 177.5(3) . . . . ? C3 C4 C9 O4 -1.6(5) . . . . ? C5 C4 C9 C8 -3.8(5) . . . . ? C3 C4 C9 C8 177.1(3) . . . . ? C7 C8 C9 O4 -147.0(4) . . . . ? C7 C8 C9 C4 34.3(5) . . . . ? C1 O2 C10 O3 -4.2(5) . . . . ? C1 O2 C10 C11 177.0(3) . . . . ? O3 C10 C11 C16 -163.5(4) . . . . ? O2 C10 C11 C16 15.2(5) . . . . ? O3 C10 C11 C12 14.9(6) . . . . ? O2 C10 C11 C12 -166.4(3) . . . . ? C16 C11 C12 C13 1.1(6) . . . . ? C10 C11 C12 C13 -177.4(4) . . . . ? C11 C12 C13 C14 0.4(7) . . . . ? C12 C13 C14 C15 -0.6(7) . . . . ? C12 C13 C14 Br1 -179.5(3) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? Br1 C14 C15 C16 178.3(3) . . . . ? C12 C11 C16 C15 -2.3(6) . . . . ? C10 C11 C16 C15 176.1(4) . . . . ? C14 C15 C16 C11 2.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.680 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.106