Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Nicolas Heureux' _publ_contact_author_address ; Departement de Chimie Universite catholique de Louvain Unite de Chimie Organique et Medici Place Pasteur, 1 Louvain-la-Neuve 1348 BELGIUM ; _publ_section_title ; Short, asymmetric synthesis of epi-morphine ACNO analogues ; _publ_contact_author_email HEUREUX@CHIM.UCL.AC.BE loop_ _publ_author_name N.Heureux I.Marko B.Norberg J.Wouters data_uclnh3b _database_code_depnum_ccdc_archive 'CCDC 608856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 N O3' _chemical_formula_sum 'C22 H23 N O3' _chemical_formula_weight 349.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc ' 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 11.945(1) _cell_length_b 11.653(2) _cell_length_c 16.339(2) _cell_angle_alpha 90.00 _cell_angle_beta 127.717(7) _cell_angle_gamma 90.00 _cell_volume 1799.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.7 _cell_measurement_theta_max 37.6 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.684 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7620 _exptl_absorpt_correction_T_max 0.8057 _exptl_absorpt_process_details '(Alcock, 1970)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type nonius _diffrn_measurement_method \q/q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 5 _diffrn_reflns_number 3857 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.68 _diffrn_reflns_theta_max 75.02 _reflns_number_total 3696 _reflns_number_gt 3464 _reflns_threshold_expression >2sigma(I) _computing_data_collection NoniusCAD4/MACH3(2000) _computing_cell_refinement NoniusCAD4/MACH3(2000) _computing_data_reduction 'Platon2001 (Spek, 2001)' _computing_structure_solution 'SIR97(Altomare, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0614P)^2^+0.3753P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0096(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3696 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.32134(9) 0.67960(8) 0.41476(7) 0.0499(2) Uani 1 1 d . . . O2 O -0.12107(10) 0.33083(8) 0.12610(7) 0.0463(2) Uani 1 1 d . . . O3 O -0.18867(9) 0.51339(8) 0.13584(7) 0.0451(2) Uani 1 1 d . . . N2 N 0.34844(10) 0.52639(9) 0.34496(8) 0.0405(2) Uani 1 1 d . . . C1 C 0.05487(11) 0.47179(9) 0.22525(8) 0.0335(2) Uani 1 1 d . . . C2 C -0.08675(12) 0.42097(10) 0.19362(9) 0.0382(3) Uani 1 1 d . . . C3 C -0.14238(13) 0.57213(11) 0.08860(9) 0.0413(3) Uani 1 1 d . . . C4 C -0.22409(16) 0.64884(13) 0.00836(10) 0.0531(3) Uani 1 1 d . . . H4 H -0.3179 0.6631 -0.0197 0.064 Uiso 1 1 calc R . . C5 C -0.15983(18) 0.70397(12) -0.02877(10) 0.0562(4) Uani 1 1 d . . . H5 H -0.2112 0.7571 -0.0821 0.067 Uiso 1 1 calc R . . C6 C -0.02196(17) 0.68122(12) 0.01195(10) 0.0523(3) Uani 1 1 d . . . H6 H 0.0183 0.7185 -0.0147 0.063 Uiso 1 1 calc R . . C7 C 0.05867(14) 0.60295(11) 0.09284(9) 0.0427(3) Uani 1 1 d . . . H7 H 0.1521 0.5880 0.1202 0.051 Uiso 1 1 calc R . . C8 C -0.00246(12) 0.54794(10) 0.13165(8) 0.0362(3) Uani 1 1 d . . . C9 C 0.16031(13) 0.37690(10) 0.25209(10) 0.0402(3) Uani 1 1 d . . . H9A H 0.1786 0.3322 0.3092 0.048 Uiso 1 1 calc R . . H9B H 0.1187 0.3261 0.1931 0.048 Uiso 1 1 calc R . . C10 C 0.29868(14) 0.42247(12) 0.28138(11) 0.0481(3) Uani 1 1 d . . . H10A H 0.3703 0.3633 0.3189 0.058 Uiso 1 1 calc R . . H10B H 0.2878 0.4388 0.2186 0.058 Uiso 1 1 calc R . . C11 C 0.27206(12) 0.59064(10) 0.36252(8) 0.0363(3) Uani 1 1 d . . . C12 C 0.12360(11) 0.55262(10) 0.32006(8) 0.0345(3) Uani 1 1 d . . . H12 H 0.0655 0.6222 0.2951 0.041 Uiso 1 1 calc R . . C13 C 0.12252(14) 0.50471(12) 0.40744(9) 0.0451(3) Uani 1 1 d . . . H13A H 0.1801 0.4359 0.4358 0.054 Uiso 1 1 calc R . . H13B H 0.1625 0.5609 0.4625 0.054 Uiso 1 1 calc R . . C14 C -0.02831(15) 0.47677(13) 0.36558(11) 0.0503(3) Uani 1 1 d . . . H14A H -0.0288 0.4485 0.4212 0.060 Uiso 1 1 calc R . . H14B H -0.0855 0.5458 0.3380 0.060 Uiso 1 1 calc R . . C15 C -0.09096(14) 0.38668(12) 0.28106(10) 0.0458(3) Uani 1 1 d . . . H15A H -0.0392 0.3154 0.3111 0.055 Uiso 1 1 calc R . . H15B H -0.1884 0.3728 0.2532 0.055 Uiso 1 1 calc R . . C16 C 0.49101(13) 0.56381(13) 0.38376(10) 0.0494(3) Uani 1 1 d . . . H16A H 0.5580 0.5023 0.4237 0.059 Uiso 1 1 calc R . . H16B H 0.5193 0.6293 0.4292 0.059 Uiso 1 1 calc R . . C17 C 0.49492(12) 0.59630(11) 0.29599(10) 0.0449(3) Uani 1 1 d . . . C18 C 0.57211(16) 0.53341(15) 0.27474(13) 0.0606(4) Uani 1 1 d . . . H18 H 0.6281 0.4729 0.3179 0.073 Uiso 1 1 calc R . . C19 C 0.5674(2) 0.55917(18) 0.18975(15) 0.0741(5) Uani 1 1 d . . . H19 H 0.6209 0.5165 0.1769 0.089 Uiso 1 1 calc R . . C20 C 0.48410(18) 0.64713(16) 0.12468(14) 0.0672(4) Uani 1 1 d . . . H20 H 0.4789 0.6629 0.0666 0.081 Uiso 1 1 calc R . . C21 C 0.40906(18) 0.71133(14) 0.14557(14) 0.0654(4) Uani 1 1 d . . . H21 H 0.3531 0.7716 0.1019 0.078 Uiso 1 1 calc R . . C22 C 0.41557(16) 0.68747(13) 0.23118(13) 0.0567(4) Uani 1 1 d . . . H22 H 0.3659 0.7334 0.2456 0.068 Uiso 1 1 calc R . . H2A H -0.1929(19) 0.2916(15) 0.1144(13) 0.063(5) Uiso 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 0.0387(5) 0.0481(5) 0.0522(5) -0.0147(4) 0.0224(4) -0.0027(4) O2 0.0490(5) 0.0454(5) 0.0483(5) -0.0098(4) 0.0317(4) -0.0134(4) O3 0.0367(4) 0.0523(5) 0.0460(5) 0.0064(4) 0.0251(4) 0.0043(4) N2 0.0323(5) 0.0473(6) 0.0395(5) -0.0033(4) 0.0207(4) 0.0017(4) C1 0.0347(5) 0.0341(5) 0.0335(5) -0.0007(4) 0.0218(5) -0.0004(4) C2 0.0374(6) 0.0391(6) 0.0390(6) 0.0002(5) 0.0239(5) -0.0011(5) C3 0.0426(6) 0.0416(6) 0.0371(6) -0.0001(5) 0.0230(5) 0.0003(5) C4 0.0502(7) 0.0540(8) 0.0424(7) 0.0056(6) 0.0219(6) 0.0102(6) C5 0.0751(10) 0.0457(7) 0.0381(6) 0.0070(5) 0.0297(7) 0.0068(7) C6 0.0767(10) 0.0446(7) 0.0423(7) -0.0024(5) 0.0397(7) -0.0091(6) C7 0.0511(7) 0.0431(6) 0.0386(6) -0.0059(5) 0.0299(6) -0.0072(5) C8 0.0414(6) 0.0334(5) 0.0323(5) -0.0034(4) 0.0219(5) -0.0019(4) C9 0.0431(6) 0.0350(6) 0.0435(6) -0.0018(5) 0.0270(5) 0.0030(5) C10 0.0431(7) 0.0462(7) 0.0586(8) -0.0077(6) 0.0329(6) 0.0044(5) C11 0.0335(5) 0.0392(6) 0.0309(5) 0.0007(4) 0.0169(5) 0.0035(4) C12 0.0332(5) 0.0358(6) 0.0331(5) -0.0013(4) 0.0195(5) 0.0028(4) C13 0.0474(7) 0.0544(7) 0.0351(6) -0.0020(5) 0.0260(5) -0.0002(6) C14 0.0536(8) 0.0633(8) 0.0468(7) -0.0019(6) 0.0373(6) -0.0023(6) C15 0.0466(7) 0.0509(7) 0.0475(7) 0.0022(6) 0.0327(6) -0.0047(5) C16 0.0307(6) 0.0659(8) 0.0445(7) -0.0045(6) 0.0194(5) -0.0001(5) C17 0.0313(5) 0.0497(7) 0.0476(7) -0.0020(5) 0.0211(5) -0.0028(5) C18 0.0529(8) 0.0700(10) 0.0645(9) 0.0141(8) 0.0387(7) 0.0187(7) C19 0.0729(11) 0.0915(13) 0.0799(11) 0.0109(10) 0.0580(10) 0.0176(10) C20 0.0618(9) 0.0808(11) 0.0628(9) 0.0098(8) 0.0400(8) -0.0067(8) C21 0.0600(9) 0.0564(9) 0.0730(10) 0.0171(8) 0.0373(8) 0.0017(7) C22 0.0506(8) 0.0482(8) 0.0724(9) 0.0037(7) 0.0382(7) 0.0045(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 C11 1.2389(15) . ? O2 C2 1.3911(14) . ? O2 H2A 0.884(18) . ? O3 C3 1.3757(15) . ? O3 C2 1.4584(14) . ? N2 C11 1.3400(15) . ? N2 C10 1.4640(16) . ? N2 C16 1.4735(16) . ? C1 C8 1.5212(15) . ? C1 C9 1.5249(16) . ? C1 C12 1.5508(15) . ? C1 C2 1.5523(15) . ? C2 C15 1.5137(16) . ? C3 C4 1.3802(18) . ? C3 C8 1.3889(17) . ? C4 C5 1.393(2) . ? C4 H4 0.9300 . ? C5 C6 1.373(2) . ? C5 H5 0.9300 . ? C6 C7 1.3960(19) . ? C6 H6 0.9300 . ? C7 C8 1.3831(17) . ? C7 H7 0.9300 . ? C9 C10 1.5084(18) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.5223(15) . ? C12 C13 1.5403(16) . ? C12 H12 0.9800 . ? C13 C14 1.5206(19) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.5182(19) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.5113(19) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.3784(19) . ? C17 C22 1.3858(19) . ? C18 C19 1.387(2) . ? C18 H18 0.9300 . ? C19 C20 1.370(3) . ? C19 H19 0.9300 . ? C20 C21 1.362(3) . ? C20 H20 0.9300 . ? C21 C22 1.381(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2A 109.7(11) . . ? C3 O3 C2 105.53(9) . . ? C11 N2 C10 125.45(10) . . ? C11 N2 C16 120.11(11) . . ? C10 N2 C16 114.25(10) . . ? C8 C1 C9 119.79(9) . . ? C8 C1 C12 106.72(9) . . ? C9 C1 C12 108.28(9) . . ? C8 C1 C2 99.16(9) . . ? C9 C1 C2 111.05(9) . . ? C12 C1 C2 111.55(9) . . ? O2 C2 O3 108.66(9) . . ? O2 C2 C15 112.67(10) . . ? O3 C2 C15 108.02(10) . . ? O2 C2 C1 106.53(9) . . ? O3 C2 C1 104.00(9) . . ? C15 C2 C1 116.43(10) . . ? O3 C3 C4 124.18(12) . . ? O3 C3 C8 112.77(10) . . ? C4 C3 C8 123.03(12) . . ? C3 C4 C5 117.04(13) . . ? C3 C4 H4 121.5 . . ? C5 C4 H4 121.5 . . ? C6 C5 C4 121.15(13) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.89(13) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 119.01(13) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C3 118.88(11) . . ? C7 C8 C1 133.80(11) . . ? C3 C8 C1 106.84(10) . . ? C10 C9 C1 112.82(10) . . ? C10 C9 H9A 109.0 . . ? C1 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C1 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N2 C10 C9 114.00(10) . . ? N2 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? N2 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.6 . . ? O1 C11 N2 121.08(11) . . ? O1 C11 C12 119.18(10) . . ? N2 C11 C12 119.72(10) . . ? C11 C12 C13 110.55(9) . . ? C11 C12 C1 112.91(9) . . ? C13 C12 C1 113.97(9) . . ? C11 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? C1 C12 H12 106.3 . . ? C14 C13 C12 109.89(10) . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 110.26(11) . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C2 C15 C14 113.17(11) . . ? C2 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? C2 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.8 . . ? N2 C16 C17 111.37(10) . . ? N2 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? N2 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C22 117.73(14) . . ? C18 C17 C16 121.30(13) . . ? C22 C17 C16 120.90(12) . . ? C17 C18 C19 120.86(15) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 120.30(16) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 119.56(16) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.37(15) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 121.12(14) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? 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 C3 O3 C2 O2 -81.79(11) . . . . ? C3 O3 C2 C15 155.69(10) . . . . ? C3 O3 C2 C1 31.39(11) . . . . ? C8 C1 C2 O2 81.79(10) . . . . ? C9 C1 C2 O2 -45.17(12) . . . . ? C12 C1 C2 O2 -166.07(9) . . . . ? C8 C1 C2 O3 -32.91(10) . . . . ? C9 C1 C2 O3 -159.87(9) . . . . ? C12 C1 C2 O3 79.23(11) . . . . ? C8 C1 C2 C15 -151.59(10) . . . . ? C9 C1 C2 C15 81.45(13) . . . . ? C12 C1 C2 C15 -39.45(14) . . . . ? C2 O3 C3 C4 164.46(12) . . . . ? C2 O3 C3 C8 -16.76(13) . . . . ? O3 C3 C4 C5 178.02(12) . . . . ? C8 C3 C4 C5 -0.6(2) . . . . ? C3 C4 C5 C6 1.0(2) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C5 C6 C7 C8 0.14(19) . . . . ? C6 C7 C8 C3 0.21(17) . . . . ? C6 C7 C8 C1 -170.66(11) . . . . ? O3 C3 C8 C7 -178.74(10) . . . . ? C4 C3 C8 C7 0.06(18) . . . . ? O3 C3 C8 C1 -5.62(13) . . . . ? C4 C3 C8 C1 173.18(12) . . . . ? C9 C1 C8 C7 -43.98(18) . . . . ? C12 C1 C8 C7 79.34(15) . . . . ? C2 C1 C8 C7 -164.75(13) . . . . ? C9 C1 C8 C3 144.37(11) . . . . ? C12 C1 C8 C3 -92.31(11) . . . . ? C2 C1 C8 C3 23.60(11) . . . . ? C8 C1 C9 C10 64.28(14) . . . . ? C12 C1 C9 C10 -58.28(13) . . . . ? C2 C1 C9 C10 178.92(10) . . . . ? C11 N2 C10 C9 -11.67(18) . . . . ? C16 N2 C10 C9 173.35(11) . . . . ? C1 C9 C10 N2 39.67(15) . . . . ? C10 N2 C11 O1 -177.60(12) . . . . ? C16 N2 C11 O1 -2.89(18) . . . . ? C10 N2 C11 C12 3.93(18) . . . . ? C16 N2 C11 C12 178.64(10) . . . . ? O1 C11 C12 C13 -73.18(14) . . . . ? N2 C11 C12 C13 105.32(12) . . . . ? O1 C11 C12 C1 157.81(10) . . . . ? N2 C11 C12 C1 -23.69(15) . . . . ? C8 C1 C12 C11 -80.79(11) . . . . ? C9 C1 C12 C11 49.41(12) . . . . ? C2 C1 C12 C11 171.91(9) . . . . ? C8 C1 C12 C13 151.98(10) . . . . ? C9 C1 C12 C13 -77.82(12) . . . . ? C2 C1 C12 C13 44.68(13) . . . . ? C11 C12 C13 C14 175.13(10) . . . . ? C1 C12 C13 C14 -56.44(14) . . . . ? C12 C13 C14 C15 60.73(14) . . . . ? O2 C2 C15 C14 169.47(11) . . . . ? O3 C2 C15 C14 -70.50(13) . . . . ? C1 C2 C15 C14 45.97(15) . . . . ? C13 C14 C15 C2 -55.97(15) . . . . ? C11 N2 C16 C17 -111.92(13) . . . . ? C10 N2 C16 C17 63.35(15) . . . . ? N2 C16 C17 C18 -113.73(15) . . . . ? N2 C16 C17 C22 63.29(17) . . . . ? C22 C17 C18 C19 -1.5(2) . . . . ? C16 C17 C18 C19 175.56(15) . . . . ? C17 C18 C19 C20 -0.8(3) . . . . ? C18 C19 C20 C21 1.9(3) . . . . ? C19 C20 C21 C22 -0.6(3) . . . . ? C20 C21 C22 C17 -1.8(2) . . . . ? C18 C17 C22 C21 2.8(2) . . . . ? C16 C17 C22 C21 -174.29(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 75.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.278 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.034 # Attachment 'Short, asymmetric synthesis of epi-morphine ACNO analogues #compound 142.cif' data_uclnh4 _database_code_depnum_ccdc_archive 'CCDC 608857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 N2 O4' _chemical_formula_sum 'C24 H24 N2 O4' _chemical_formula_weight 404.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall C-2yc _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.576(3) _cell_length_b 15.667(2) _cell_length_c 7.4650(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.461(11) _cell_angle_gamma 90.00 _cell_volume 2055.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 17.7 _cell_measurement_theta_max 37.9 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7850 _exptl_absorpt_correction_T_max 0.8988 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type nonius _diffrn_measurement_method \q/q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1.3 _diffrn_reflns_number 2287 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0100 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 74.94 _reflns_number_total 2287 _reflns_number_gt 2235 _reflns_threshold_expression >2sigma(I) _computing_data_collection NoniusCAD4/MACH3(2000) _computing_cell_refinement NoniusCAD4/MACH3(2000) _computing_data_reduction 'Platon2001 (Spek, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0787P)^2^+0.2740P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration rm _refine_ls_number_reflns 2287 _refine_ls_number_parameters 271 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.53226(13) 0.59101(15) 1.0718(3) 0.0697(5) Uani 1 1 d . . . O2 O 0.37209(13) 0.51419(11) 0.9090(4) 0.0725(6) Uani 1 1 d . . . O3 O 0.75062(14) 0.54418(14) 0.7208(4) 0.0758(6) Uani 1 1 d . . . O4 O 0.76037(10) 0.65273(13) 0.5290(3) 0.0637(5) Uani 1 1 d . . . N1 N 0.43053(12) 0.72874(15) 0.3946(3) 0.0562(5) Uani 1 1 d . . . N2 N 0.62598(11) 0.62846(12) 0.8832(3) 0.0464(4) Uani 1 1 d . . . C1 C 0.51679(12) 0.67155(14) 0.6095(3) 0.0439(5) Uani 1 1 d . . . C2 C 0.46206(14) 0.66069(17) 0.4514(4) 0.0531(5) Uani 1 1 d . . . H2 H 0.4524 0.6076 0.4005 0.064 Uiso 1 1 d R . . C3 C 0.45898(12) 0.79650(16) 0.5040(3) 0.0486(5) Uani 1 1 d . . . C4 C 0.43828(16) 0.88148(18) 0.4933(4) 0.0611(6) Uani 1 1 d . . . H4 H 0.4026 0.9001 0.4094 0.073 Uiso 1 1 d R . . C5 C 0.47237(17) 0.93800(17) 0.6114(5) 0.0644(7) Uani 1 1 d . . . H5 H 0.4600 0.9957 0.6054 0.077 Uiso 1 1 d R . . C6 C 0.52433(16) 0.91045(15) 0.7380(4) 0.0575(6) Uani 1 1 d . . . H6A H 0.5466 0.9496 0.8161 0.069 Uiso 1 1 d R . . C7 C 0.54418(14) 0.82438(14) 0.7499(3) 0.0482(5) Uani 1 1 d . . . H7A H 0.5788 0.8057 0.8362 0.058 Uiso 1 1 d R . . C8 C 0.51127(12) 0.76732(13) 0.6317(3) 0.0426(4) Uani 1 1 d . . . C9 C 0.59572(13) 0.63752(15) 0.5585(3) 0.0460(5) Uani 1 1 d . . . H9A H 0.5926 0.5765 0.5372 0.060 Uiso 1 1 d R . . H9B H 0.6125 0.6647 0.4489 0.060 Uiso 1 1 d R . . C10 C 0.65331(12) 0.65493(14) 0.7087(3) 0.0442(5) Uani 1 1 d . . . H10 H 0.6634 0.7164 0.7124 0.053 Uiso 1 1 d R . . C11 C 0.55185(14) 0.61131(13) 0.9203(3) 0.0476(5) Uani 1 1 d . . . C12 C 0.49100(12) 0.61905(13) 0.7735(3) 0.0451(5) Uani 1 1 d . . . H12A H 0.4796 0.5612 0.7310 0.054 Uiso 1 1 d R . . C13 C 0.41828(13) 0.65429(15) 0.8564(4) 0.0516(5) Uani 1 1 d . . . H13A H 0.4325 0.6964 0.9459 0.067 Uiso 1 1 d R . . H13B H 0.3892 0.6834 0.7639 0.067 Uiso 1 1 d R . . C14 C 0.36763(14) 0.58868(15) 0.9429(4) 0.0494(5) Uani 1 1 d . . . C15 C 0.30875(17) 0.6232(2) 1.0676(5) 0.0662(7) Uani 1 1 d . . . H15A H 0.2838 0.5767 1.1266 0.099 Uiso 1 1 d R . . H15B H 0.2720 0.6557 1.0006 0.099 Uiso 1 1 d R . . H15C H 0.3327 0.6593 1.1554 0.099 Uiso 1 1 d R . . C16 C 0.67796(15) 0.64351(17) 1.0355(4) 0.0526(5) Uani 1 1 d . . . H16A H 0.7287 0.6244 1.0044 0.068 Uiso 1 1 d R . . H16B H 0.6612 0.6105 1.1379 0.068 Uiso 1 1 d R . . C17 C 0.68071(13) 0.73707(16) 1.0847(3) 0.0477(5) Uani 1 1 d . . . C18 C 0.74122(14) 0.7883(2) 1.0310(4) 0.0594(6) Uani 1 1 d . . . H18 H 0.7818 0.7638 0.9705 0.071 Uiso 1 1 d R . . C19 C 0.74157(18) 0.8745(2) 1.0663(5) 0.0716(8) Uani 1 1 d . . . H19 H 0.7815 0.9082 1.0263 0.086 Uiso 1 1 d R . . C20 C 0.6828(2) 0.9113(2) 1.1609(5) 0.0725(8) Uani 1 1 d . . . H20 H 0.6838 0.9694 1.1870 0.087 Uiso 1 1 d R . . C21 C 0.62287(17) 0.86194(19) 1.2156(4) 0.0638(7) Uani 1 1 d . . . H21 H 0.5833 0.8865 1.2797 0.077 Uiso 1 1 d R . . C22 C 0.62134(14) 0.77570(16) 1.1770(3) 0.0532(6) Uani 1 1 d . . . H22 H 0.5799 0.7430 1.2122 0.064 Uiso 1 1 d R . . C23 C 0.72719(14) 0.60879(14) 0.6583(4) 0.0493(5) Uani 1 1 d . . . C24 C 0.82940(17) 0.6179(2) 0.4544(6) 0.0766(9) Uani 1 1 d . . . H24A H 0.8702 0.6237 0.5396 0.115 Uiso 1 1 d R . . H24B H 0.8419 0.6482 0.3469 0.115 Uiso 1 1 d R . . H24C H 0.8219 0.5587 0.4271 0.115 Uiso 1 1 d 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 0.0700(12) 0.0810(13) 0.0585(11) 0.0155(10) 0.0138(9) -0.0087(10) O2 0.0724(11) 0.0435(9) 0.1020(16) -0.0008(10) 0.0305(11) -0.0132(8) O3 0.0820(13) 0.0616(11) 0.0838(14) 0.0070(10) 0.0122(11) 0.0291(10) O4 0.0504(9) 0.0615(10) 0.0795(13) 0.0042(9) 0.0210(9) 0.0074(7) N1 0.0443(9) 0.0672(13) 0.0571(11) 0.0024(10) -0.0013(8) -0.0005(9) N2 0.0482(10) 0.0431(9) 0.0479(10) 0.0052(7) 0.0029(8) 0.0026(7) C1 0.0397(10) 0.0410(10) 0.0509(11) 0.0015(9) 0.0029(9) -0.0031(8) C2 0.0442(11) 0.0575(13) 0.0577(14) -0.0050(11) 0.0028(10) -0.0076(10) C3 0.0367(9) 0.0560(12) 0.0532(12) 0.0089(10) 0.0061(9) 0.0005(9) C4 0.0557(13) 0.0625(14) 0.0652(15) 0.0196(13) 0.0045(12) 0.0153(11) C5 0.0688(15) 0.0423(11) 0.0824(18) 0.0140(12) 0.0144(14) 0.0118(11) C6 0.0641(14) 0.0402(11) 0.0683(15) 0.0006(11) 0.0088(12) -0.0006(10) C7 0.0494(11) 0.0421(10) 0.0532(12) 0.0047(9) 0.0028(10) 0.0012(8) C8 0.0385(9) 0.0396(10) 0.0498(11) 0.0074(9) 0.0078(8) -0.0010(8) C9 0.0437(10) 0.0463(10) 0.0479(11) -0.0018(9) 0.0055(9) 0.0023(8) C10 0.0442(11) 0.0380(9) 0.0506(11) -0.0018(8) 0.0069(9) 0.0018(8) C11 0.0536(12) 0.0372(9) 0.0520(12) 0.0051(9) 0.0105(10) -0.0033(8) C12 0.0445(11) 0.0324(9) 0.0584(12) 0.0012(8) 0.0108(9) -0.0043(7) C13 0.0464(11) 0.0392(10) 0.0696(15) 0.0049(10) 0.0153(10) -0.0012(8) C14 0.0451(10) 0.0460(11) 0.0574(12) 0.0043(10) 0.0073(9) -0.0054(9) C15 0.0606(15) 0.0654(16) 0.0728(18) 0.0009(14) 0.0213(14) -0.0061(12) C16 0.0520(12) 0.0569(12) 0.0489(12) 0.0057(10) 0.0009(10) 0.0077(10) C17 0.0431(10) 0.0566(12) 0.0435(11) 0.0068(9) -0.0017(9) -0.0001(9) C18 0.0415(11) 0.0758(16) 0.0609(15) -0.0029(13) 0.0046(10) -0.0071(11) C19 0.0617(16) 0.0751(18) 0.0782(19) 0.0004(16) 0.0105(14) -0.0257(14) C20 0.0772(18) 0.0563(14) 0.084(2) -0.0042(14) 0.0076(16) -0.0132(14) C21 0.0647(16) 0.0596(14) 0.0673(16) -0.0041(13) 0.0149(13) 0.0017(12) C22 0.0510(12) 0.0561(14) 0.0527(12) 0.0085(10) 0.0099(10) -0.0051(10) C23 0.0450(11) 0.0443(10) 0.0586(13) -0.0034(10) 0.0021(9) 0.0048(9) C24 0.0532(14) 0.082(2) 0.095(2) -0.0103(18) 0.0261(16) 0.0056(14) _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 C11 1.227(3) . ? O2 C14 1.197(3) . ? O3 C23 1.187(3) . ? O4 C23 1.325(3) . ? O4 C24 1.446(3) . ? N1 C2 1.273(4) . ? N1 C3 1.427(3) . ? N2 C11 1.361(3) . ? N2 C10 1.453(3) . ? N2 C16 1.472(3) . ? C1 C8 1.513(3) . ? C1 C2 1.526(3) . ? C1 C9 1.537(3) . ? C1 C12 1.546(3) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 C8 1.396(3) . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 H5 0.9300 . ? C6 C7 1.396(3) . ? C6 H6A 0.9300 . ? C7 C8 1.380(3) . ? C7 H7A 0.9299 . ? C9 C10 1.529(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C23 1.536(3) . ? C10 H10 0.9800 . ? C11 C12 1.530(3) . ? C12 C13 1.528(3) . ? C12 H12A 0.9800 . ? C13 C14 1.508(3) . ? C13 H13A 0.9701 . ? C13 H13B 0.9700 . ? C14 C15 1.498(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9599 . ? C15 H15C 0.9600 . ? C16 C17 1.512(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.394(3) . ? C17 C22 1.393(3) . ? C18 C19 1.376(5) . ? C18 H18 0.9302 . ? C19 C20 1.382(5) . ? C19 H19 0.9300 . ? C20 C21 1.372(4) . ? C20 H20 0.9299 . ? C21 C22 1.382(4) . ? C21 H21 0.9301 . ? C22 H22 0.9300 . ? C24 H24A 0.9593 . ? C24 H24B 0.9594 . ? C24 H24C 0.9594 . ? 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 C23 O4 C24 117.4(2) . . ? C2 N1 C3 106.4(2) . . ? C11 N2 C10 124.2(2) . . ? C11 N2 C16 117.6(2) . . ? C10 N2 C16 116.06(19) . . ? C8 C1 C2 98.90(19) . . ? C8 C1 C9 115.47(17) . . ? C2 C1 C9 109.53(19) . . ? C8 C1 C12 114.94(19) . . ? C2 C1 C12 111.48(18) . . ? C9 C1 C12 106.41(18) . . ? N1 C2 C1 115.7(2) . . ? N1 C2 H2 122.4 . . ? C1 C2 H2 121.8 . . ? C4 C3 C8 121.8(2) . . ? C4 C3 N1 126.3(2) . . ? C8 C3 N1 111.9(2) . . ? C5 C4 C3 117.9(2) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.1 . . ? C6 C5 C4 121.2(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.6 . . ? C8 C7 C6 118.8(2) . . ? C8 C7 H7A 120.5 . . ? C6 C7 H7A 120.7 . . ? C7 C8 C3 119.7(2) . . ? C7 C8 C1 133.3(2) . . ? C3 C8 C1 107.0(2) . . ? C10 C9 C1 110.50(18) . . ? C10 C9 H9A 109.4 . . ? C1 C9 H9A 109.4 . . ? C10 C9 H9B 109.7 . . ? C1 C9 H9B 109.7 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C9 112.65(18) . . ? N2 C10 C23 111.82(19) . . ? C9 C10 C23 107.01(18) . . ? N2 C10 H10 108.5 . . ? C9 C10 H10 108.3 . . ? C23 C10 H10 108.4 . . ? O1 C11 N2 121.0(2) . . ? O1 C11 C12 118.8(2) . . ? N2 C11 C12 120.2(2) . . ? C13 C12 C11 108.7(2) . . ? C13 C12 C1 112.35(18) . . ? C11 C12 C1 113.68(17) . . ? C13 C12 H12A 107.2 . . ? C11 C12 H12A 107.4 . . ? C1 C12 H12A 107.2 . . ? C14 C13 C12 115.20(19) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.3 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.5 . . ? O2 C14 C15 122.0(2) . . ? O2 C14 C13 122.3(2) . . ? C15 C14 C13 115.6(2) . . ? C14 C15 H15A 109.3 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.6 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 111.19(19) . . ? N2 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? N2 C16 H16B 109.4 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C22 117.9(2) . . ? C18 C17 C16 120.7(2) . . ? C22 C17 C16 121.2(2) . . ? C19 C18 C17 120.8(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.4(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 119.7(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 121.0(2) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.4 . . ? O3 C23 O4 125.2(2) . . ? O3 C23 C10 126.6(2) . . ? O4 C23 C10 108.18(19) . . ? O4 C24 H24A 109.6 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.4 . . ? H24A C24 H24C 109.4 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 74.94 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.175 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.035