# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jin, Zhichao' 'Yu, Feng' 'Wang, Xiao' 'Huang, Huicai' 'Luo, Xiaoyan' 'Liang, Xinmiao' 'Ye, Jinxing' _publ_contact_author_name 'Ye, Jinxing' _publ_contact_author_email yejx@ecust.edu.cn _publ_section_title ; A One-pot Asymmetric Organocatalytic Cascade Reaction for the Synthesis of Oxazine Derivatives ; _publ_contact_author_address 'School of Pharmacy, East China University of Science and Technology' _publ_contact_author_phone '0086 21 64251830' # Attachment '- YEJIN2.cif' data_YEJIN2 _database_code_depnum_ccdc_archive 'CCDC 793001' _publ_section_comment ; Discussion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Br N O5' _chemical_formula_weight 430.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2259(12) _cell_length_b 12.3386(17) _cell_length_c 9.1136(13) _cell_angle_alpha 90.00 _cell_angle_beta 97.552(2) _cell_angle_gamma 90.00 _cell_volume 917.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1784 _cell_measurement_theta_min 4.995 _cell_measurement_theta_max 46.779 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.355 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.208 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 2.273 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6354 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 5418 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3774 _reflns_number_gt 2584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0576P)^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 SHELXL _refine_ls_extinction_coef 0.014(2) _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 0.085(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 3774 _refine_ls_number_parameters 246 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _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 Br Br 0.49094(7) 0.27141(7) 0.75669(6) 0.0779(2) Uani 1 1 d . . . O1 O 0.0579(4) 0.2191(3) 0.2001(4) 0.0611(9) Uani 1 1 d . . . O2 O 0.0614(4) 0.3100(2) 0.4080(3) 0.0466(7) Uani 1 1 d . . . O3 O 0.1417(4) 0.6481(2) 0.3724(3) 0.0525(8) Uani 1 1 d . . . O4 O 0.3496(5) 0.7240(3) 0.6754(4) 0.0833(11) Uani 1 1 d . . . O5 O 0.4626(4) 0.5795(3) 0.5827(4) 0.0722(10) Uani 1 1 d . . . N1 N -0.0050(4) 0.4959(2) 0.4032(3) 0.0391(7) Uani 1 1 d . . . C1 C 0.0182(5) 0.3011(3) 0.2582(5) 0.0478(12) Uani 1 1 d . . . C2 C -0.0241(5) 0.3942(3) 0.4776(4) 0.0407(9) Uani 1 1 d . . . H2 H -0.1410 0.3760 0.4682 0.049 Uiso 1 1 calc R . . C3 C -0.0748(5) 0.4917(3) 0.2517(4) 0.0416(9) Uani 1 1 d . . . C4 C -0.0673(5) 0.3927(3) 0.1817(4) 0.0424(9) Uani 1 1 d . . . C5 C -0.1352(5) 0.3824(4) 0.0337(5) 0.0557(12) Uani 1 1 d . . . H5 H -0.1299 0.3164 -0.0149 0.067 Uiso 1 1 calc R . . C6 C -0.2096(6) 0.4698(5) -0.0398(5) 0.0626(13) Uani 1 1 d . . . H6 H -0.2560 0.4630 -0.1381 0.075 Uiso 1 1 calc R . . C7 C -0.2158(6) 0.5684(5) 0.0321(5) 0.0626(13) Uani 1 1 d . . . H7 H -0.2659 0.6276 -0.0183 0.075 Uiso 1 1 calc R . . C8 C -0.1489(6) 0.5790(4) 0.1763(5) 0.0540(11) Uani 1 1 d . . . H8 H -0.1534 0.6454 0.2239 0.065 Uiso 1 1 calc R . . C9 C 0.0443(5) 0.3958(3) 0.6394(4) 0.0447(10) Uani 1 1 d . . . H9A H 0.0543 0.3219 0.6758 0.054 Uiso 1 1 calc R . . H9B H -0.0319 0.4335 0.6942 0.054 Uiso 1 1 calc R . . C10 C 0.2103(5) 0.4506(3) 0.6675(4) 0.0388(9) Uani 1 1 d . . . H10 H 0.2851 0.4133 0.6091 0.047 Uiso 1 1 calc R . . C11 C 0.1867(5) 0.5680(3) 0.6096(4) 0.0397(9) Uani 1 1 d . . . H11 H 0.1107 0.6034 0.6687 0.048 Uiso 1 1 calc R . . C12 C 0.1095(5) 0.5742(3) 0.4500(4) 0.0398(9) Uani 1 1 d . . . C13 C 0.2809(5) 0.4438(3) 0.8285(4) 0.0445(10) Uani 1 1 d . . . C14 C 0.3944(5) 0.3668(4) 0.8852(5) 0.0518(11) Uani 1 1 d . . . C15 C 0.4466(6) 0.3564(5) 1.0334(6) 0.0676(14) Uani 1 1 d . . . H15 H 0.5182 0.3007 1.0669 0.081 Uiso 1 1 calc R . . C16 C 0.3939(7) 0.4273(5) 1.1325(5) 0.0693(16) Uani 1 1 d . . . H16 H 0.4318 0.4220 1.2329 0.083 Uiso 1 1 calc R . . C17 C 0.2843(7) 0.5064(5) 1.0807(5) 0.0659(14) Uani 1 1 d . . . H17 H 0.2471 0.5549 1.1470 0.079 Uiso 1 1 calc R . . C18 C 0.2285(6) 0.5151(4) 0.9325(5) 0.0559(12) Uani 1 1 d . . . H18 H 0.1541 0.5696 0.9003 0.067 Uiso 1 1 calc R . . C19 C 0.3399(6) 0.6339(4) 0.6272(5) 0.0534(12) Uani 1 1 d . . . C20 C 0.6204(7) 0.6345(6) 0.6032(7) 0.107(2) Uani 1 1 d . . . H20A H 0.6120 0.7014 0.5491 0.160 Uiso 1 1 calc R . . H20B H 0.7015 0.5891 0.5674 0.160 Uiso 1 1 calc R . . H20C H 0.6517 0.6491 0.7065 0.160 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 Br 0.0772(4) 0.0649(3) 0.0857(4) -0.0106(3) -0.0116(2) 0.0258(3) O1 0.064(2) 0.0486(19) 0.072(2) -0.0166(18) 0.0156(18) 0.0028(16) O2 0.0582(18) 0.0306(13) 0.0502(16) -0.0024(12) 0.0037(14) 0.0019(12) O3 0.070(2) 0.0424(16) 0.0455(17) 0.0063(14) 0.0094(15) -0.0111(14) O4 0.106(3) 0.059(2) 0.080(2) -0.0076(19) -0.006(2) -0.033(2) O5 0.0490(19) 0.077(2) 0.090(3) 0.018(2) 0.0080(18) -0.0148(18) N1 0.0433(19) 0.0326(16) 0.0403(18) -0.0002(14) 0.0015(15) -0.0025(14) C1 0.042(3) 0.046(3) 0.057(3) -0.006(2) 0.010(2) -0.005(2) C2 0.037(2) 0.036(2) 0.049(2) -0.0022(18) 0.0037(18) -0.0028(17) C3 0.036(2) 0.041(2) 0.047(2) 0.0006(18) 0.0032(18) -0.0073(18) C4 0.036(2) 0.047(2) 0.044(2) -0.0047(19) 0.0046(18) -0.0086(18) C5 0.050(3) 0.068(3) 0.050(3) -0.009(2) 0.011(2) -0.013(2) C6 0.065(3) 0.084(4) 0.038(2) 0.008(3) 0.006(2) -0.013(3) C7 0.060(3) 0.073(3) 0.052(3) 0.013(3) -0.002(2) -0.006(3) C8 0.057(3) 0.043(2) 0.060(3) 0.007(2) 0.002(2) 0.004(2) C9 0.051(3) 0.040(2) 0.041(2) 0.0021(18) 0.0019(19) -0.0077(19) C10 0.043(2) 0.032(2) 0.042(2) 0.0024(17) 0.0068(18) 0.0005(17) C11 0.047(2) 0.0309(19) 0.041(2) -0.0037(17) 0.0072(18) -0.0020(18) C12 0.044(2) 0.032(2) 0.045(2) -0.0034(18) 0.0125(19) 0.0025(18) C13 0.047(2) 0.043(2) 0.045(2) -0.0008(19) 0.008(2) -0.012(2) C14 0.049(3) 0.051(3) 0.054(3) 0.004(2) -0.001(2) -0.004(2) C15 0.053(3) 0.079(3) 0.066(3) 0.021(3) -0.010(3) -0.011(3) C16 0.062(3) 0.101(5) 0.042(3) 0.009(3) -0.006(3) -0.032(3) C17 0.068(3) 0.087(4) 0.047(3) -0.001(3) 0.020(3) -0.024(3) C18 0.059(3) 0.065(3) 0.046(3) 0.000(2) 0.014(2) -0.005(2) C19 0.061(3) 0.054(3) 0.041(2) 0.010(2) -0.010(2) -0.009(2) C20 0.055(4) 0.138(6) 0.124(5) 0.057(5) 0.000(4) -0.031(4) _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 Br C14 1.906(5) . ? O1 C1 1.206(5) . ? O2 C1 1.370(5) . ? O2 C2 1.447(5) . ? O3 C12 1.204(5) . ? O4 C19 1.194(6) . ? O5 C19 1.320(6) . ? O5 C20 1.455(6) . ? N1 C12 1.377(5) . ? N1 C3 1.425(5) . ? N1 C2 1.444(5) . ? C1 C4 1.459(6) . ? C2 C9 1.507(6) . ? C2 H2 0.9800 . ? C3 C8 1.376(6) . ? C3 C4 1.384(5) . ? C4 C5 1.397(6) . ? C5 C6 1.372(7) . ? C5 H5 0.9300 . ? C6 C7 1.385(7) . ? C6 H6 0.9300 . ? C7 C8 1.363(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.516(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.508(5) . ? C10 C11 1.545(5) . ? C10 H10 0.9800 . ? C11 C19 1.491(6) . ? C11 C12 1.510(6) . ? C11 H11 0.9800 . ? C13 C14 1.383(6) . ? C13 C18 1.402(6) . ? C14 C15 1.368(6) . ? C15 C16 1.369(7) . ? C15 H15 0.9300 . ? C16 C17 1.369(7) . ? C16 H16 0.9300 . ? C17 C18 1.372(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C1 O2 C2 114.6(3) . . ? C19 O5 C20 115.4(5) . . ? C12 N1 C3 119.8(3) . . ? C12 N1 C2 125.2(3) . . ? C3 N1 C2 111.6(3) . . ? O1 C1 O2 117.0(4) . . ? O1 C1 C4 125.5(4) . . ? O2 C1 C4 117.4(3) . . ? N1 C2 O2 109.2(3) . . ? N1 C2 C9 113.5(3) . . ? O2 C2 C9 107.3(3) . . ? N1 C2 H2 108.9 . . ? O2 C2 H2 108.9 . . ? C9 C2 H2 108.9 . . ? C8 C3 C4 120.3(4) . . ? C8 C3 N1 123.5(4) . . ? C4 C3 N1 116.2(4) . . ? C3 C4 C5 119.3(4) . . ? C3 C4 C1 120.8(3) . . ? C5 C4 C1 119.8(4) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.1(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.4(5) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C3 120.2(5) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C2 C9 C10 112.5(3) . . ? C2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C13 C10 C9 111.3(3) . . ? C13 C10 C11 113.6(3) . . ? C9 C10 C11 106.9(3) . . ? C13 C10 H10 108.3 . . ? C9 C10 H10 108.3 . . ? C11 C10 H10 108.3 . . ? C19 C11 C12 108.6(3) . . ? C19 C11 C10 114.1(4) . . ? C12 C11 C10 113.2(3) . . ? C19 C11 H11 106.8 . . ? C12 C11 H11 106.8 . . ? C10 C11 H11 106.8 . . ? O3 C12 N1 122.9(4) . . ? O3 C12 C11 120.4(4) . . ? N1 C12 C11 116.5(3) . . ? C14 C13 C18 115.5(4) . . ? C14 C13 C10 123.8(4) . . ? C18 C13 C10 120.6(4) . . ? C15 C14 C13 122.8(5) . . ? C15 C14 Br 116.5(4) . . ? C13 C14 Br 120.7(3) . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 118.7(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C16 C17 C18 121.0(5) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C17 C18 C13 121.5(5) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? O4 C19 O5 124.8(5) . . ? O4 C19 C11 124.2(5) . . ? O5 C19 C11 111.0(4) . . ? O5 C20 H20A 109.5 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C2 O2 C1 O1 -164.5(3) . . . . ? C2 O2 C1 C4 17.4(5) . . . . ? C12 N1 C2 O2 -97.2(4) . . . . ? C3 N1 C2 O2 61.8(4) . . . . ? C12 N1 C2 C9 22.4(5) . . . . ? C3 N1 C2 C9 -178.6(3) . . . . ? C1 O2 C2 N1 -53.9(4) . . . . ? C1 O2 C2 C9 -177.3(3) . . . . ? C12 N1 C3 C8 -53.7(5) . . . . ? C2 N1 C3 C8 146.0(4) . . . . ? C12 N1 C3 C4 127.3(4) . . . . ? C2 N1 C3 C4 -33.0(5) . . . . ? C8 C3 C4 C5 0.2(6) . . . . ? N1 C3 C4 C5 179.2(4) . . . . ? C8 C3 C4 C1 176.9(4) . . . . ? N1 C3 C4 C1 -4.1(6) . . . . ? O1 C1 C4 C3 -165.3(4) . . . . ? O2 C1 C4 C3 12.6(6) . . . . ? O1 C1 C4 C5 11.3(6) . . . . ? O2 C1 C4 C5 -170.7(4) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C1 C4 C5 C6 -177.4(4) . . . . ? C4 C5 C6 C7 0.7(7) . . . . ? C5 C6 C7 C8 -0.3(7) . . . . ? C6 C7 C8 C3 -0.1(7) . . . . ? C4 C3 C8 C7 0.2(7) . . . . ? N1 C3 C8 C7 -178.7(4) . . . . ? N1 C2 C9 C10 -43.7(5) . . . . ? O2 C2 C9 C10 77.0(4) . . . . ? C2 C9 C10 C13 -175.9(3) . . . . ? C2 C9 C10 C11 59.5(4) . . . . ? C13 C10 C11 C19 57.5(5) . . . . ? C9 C10 C11 C19 -179.4(3) . . . . ? C13 C10 C11 C12 -177.7(3) . . . . ? C9 C10 C11 C12 -54.5(4) . . . . ? C3 N1 C12 O3 8.6(6) . . . . ? C2 N1 C12 O3 166.1(4) . . . . ? C3 N1 C12 C11 -175.6(3) . . . . ? C2 N1 C12 C11 -18.2(5) . . . . ? C19 C11 C12 O3 -21.8(5) . . . . ? C10 C11 C12 O3 -149.6(4) . . . . ? C19 C11 C12 N1 162.3(4) . . . . ? C10 C11 C12 N1 34.5(5) . . . . ? C9 C10 C13 C14 97.7(5) . . . . ? C11 C10 C13 C14 -141.6(4) . . . . ? C9 C10 C13 C18 -79.9(4) . . . . ? C11 C10 C13 C18 40.8(5) . . . . ? C18 C13 C14 C15 3.3(6) . . . . ? C10 C13 C14 C15 -174.4(4) . . . . ? C18 C13 C14 Br -175.0(3) . . . . ? C10 C13 C14 Br 7.4(6) . . . . ? C13 C14 C15 C16 -3.7(7) . . . . ? Br C14 C15 C16 174.6(4) . . . . ? C14 C15 C16 C17 2.1(7) . . . . ? C15 C16 C17 C18 -0.3(7) . . . . ? C16 C17 C18 C13 0.1(7) . . . . ? C14 C13 C18 C17 -1.5(6) . . . . ? C10 C13 C18 C17 176.3(4) . . . . ? C20 O5 C19 O4 3.3(7) . . . . ? C20 O5 C19 C11 -176.7(4) . . . . ? C12 C11 C19 O4 99.3(5) . . . . ? C10 C11 C19 O4 -133.4(5) . . . . ? C12 C11 C19 O5 -80.7(4) . . . . ? C10 C11 C19 O5 46.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.479 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.061