#------------------------------------------------------------------------------ #$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013269.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2013269 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o274 _journal_page_last o276 _publ_section_title ; 9-\a-Fluoro-16-\a-methyl-3,11-dioxoandrosta-1,4-diene-17\b- carboxylic acid: catemeric hydrogen bonding and acetic acid solvation in a steroidal keto acid related to dexamethasone ; loop_ _publ_author_name 'Lalancette, Roger A.' 'Thompson, Hugh W.' _chemical_formula_moiety 'C21 H25 F O4 , C2 H4 O2' _chemical_formula_sum 'C23 H29 F O6' _chemical_formula_weight 420.46 _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.823(3) _cell_length_b 11.269(4) _cell_length_c 15.407(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.860(15) _cell_angle_gamma 90.00 _cell_volume 2170.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _exptl_crystal_density_diffrn 1.287 _diffrn_ambient_temperature 296(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol F1 0.0493(2) 0.5035(3) 0.1348(2) 0.0579(9) Uani d . 1 . . F F1' 0.6869(2) 0.6472(3) 0.60451(19) 0.0415(7) Uani d . 1 . . F O1 -0.3024(3) 0.6077(4) 0.1999(3) 0.0730(14) Uani d . 1 . . O O2 0.2184(3) 0.6098(4) 0.3119(4) 0.0774(15) Uani d . 1 . . O O3 0.5654(4) 0.3290(5) 0.1748(4) 0.0829(15) Uani d . 1 . . O O4 0.5051(3) 0.5100(5) 0.1374(3) 0.0777(15) Uani d . 1 . . O H4B 0.5673 0.5280 0.1598 0.117 Uiso calc R 1 . . H O1' 1.0295(3) 0.7026(3) 0.5220(3) 0.0547(11) Uani d . 1 . . O O2' 0.5180(3) 0.6056(4) 0.4127(3) 0.0559(11) Uani d . 1 . . O O3' 0.1907(3) 0.4830(4) 0.6594(3) 0.0767(14) Uani d . 1 . . O O4' 0.2312(3) 0.6447(4) 0.5914(3) 0.0701(13) Uani d . 1 . . O H4'B 0.1659 0.6490 0.5753 0.105 Uiso calc R 1 . . H C1 -0.0204(5) 0.6175(5) 0.2729(5) 0.0573(17) Uani d . 1 . . C H1A 0.0327 0.6748 0.2885 0.069 Uiso calc R 1 . . H C2 -0.1195(5) 0.6532(6) 0.2478(4) 0.0603(17) Uani d . 1 . . C H2A -0.1333 0.7342 0.2484 0.072 Uiso calc R 1 . . H C3 -0.2086(5) 0.5736(6) 0.2193(4) 0.0536(16) Uani d . 1 . . C C4 -0.1805(5) 0.4471(6) 0.2189(4) 0.0559(16) Uani d . 1 . . C H4A -0.2355 0.3925 0.2009 0.067 Uiso calc R 1 . . H C5 -0.0813(4) 0.4066(5) 0.2429(4) 0.0484(15) Uani d . 1 . . C C6 -0.0547(5) 0.2785(6) 0.2387(4) 0.0532(16) Uani d . 1 . . C H6A -0.1189 0.2346 0.2121 0.064 Uiso calc R 1 . . H H6B -0.0281 0.2485 0.2985 0.064 Uiso calc R 1 . . H C7 0.0301(4) 0.2590(6) 0.1837(4) 0.0534(16) Uani d . 1 . . C H7A 0.0502 0.1759 0.1863 0.064 Uiso calc R 1 . . H H7B -0.0002 0.2788 0.1220 0.064 Uiso calc R 1 . . H C8 0.1300(4) 0.3347(5) 0.2176(4) 0.0408(13) Uani d . 1 . . C H8A 0.1647 0.3079 0.2776 0.049 Uiso calc R 1 . . H C9 0.0990(4) 0.4667(5) 0.2223(4) 0.0417(13) Uani d . 1 . . C C10 0.0128(4) 0.4886(6) 0.2782(4) 0.0477(14) Uani d . 1 . . C C11 0.2003(4) 0.5447(6) 0.2463(5) 0.0537(16) Uani d . 1 . . C C12 0.2782(5) 0.5323(5) 0.1863(4) 0.0525(15) Uani d . 1 . . C H12A 0.3405 0.5821 0.2073 0.063 Uiso calc R 1 . . H H12B 0.2447 0.5556 0.1259 0.063 Uiso calc R 1 . . H C13 0.3111(4) 0.3993(5) 0.1894(3) 0.0416(14) Uani d . 1 . . C C14 0.2097(4) 0.3233(5) 0.1580(4) 0.0418(13) Uani d . 1 . . C H14A 0.1738 0.3527 0.0990 0.050 Uiso calc R 1 . . H C15 0.2532(5) 0.2010(6) 0.1445(4) 0.0540(16) Uani d . 1 . . C H15A 0.2024 0.1565 0.1003 0.065 Uiso calc R 1 . . H H15B 0.2685 0.1567 0.1999 0.065 Uiso calc R 1 . . H C16 0.3568(5) 0.2253(6) 0.1120(4) 0.0580(17) Uani d . 1 . . C H16A 0.4160 0.1850 0.1524 0.070 Uiso calc R 1 . . H C17 0.3762(4) 0.3599(6) 0.1211(4) 0.0520(16) Uani d . 1 . . C H17A 0.3449 0.3972 0.0637 0.062 Uiso calc R 1 . . H C18 0.3738(4) 0.3681(6) 0.2844(4) 0.0510(15) Uani d . 1 . . C H18A 0.3947 0.2861 0.2865 0.077 Uiso calc R 1 . . H H18B 0.3292 0.3816 0.3258 0.077 Uiso calc R 1 . . H H18C 0.4364 0.4171 0.2998 0.077 Uiso calc R 1 . . H C19 0.0595(5) 0.4596(7) 0.3782(4) 0.0603(18) Uani d . 1 . . C H19A 0.0060 0.4740 0.4117 0.091 Uiso calc R 1 . . H H19B 0.1205 0.5090 0.4004 0.091 Uiso calc R 1 . . H H19C 0.0806 0.3777 0.3841 0.091 Uiso calc R 1 . . H C20 0.4916(5) 0.3939(7) 0.1472(4) 0.0574(17) Uani d . 1 . . C C21 0.3513(7) 0.1797(8) 0.0167(5) 0.091(3) Uani d . 1 . . C H21A 0.4174 0.1969 0.0000 0.137 Uiso calc R 1 . . H H21B 0.2935 0.2183 -0.0238 0.137 Uiso calc R 1 . . H H21C 0.3394 0.0955 0.0148 0.137 Uiso calc R 1 . . H C22 1.0145(6) 0.3992(9) 0.8961(5) 0.081(2) Uani d . 1 . . C C23 1.1144(7) 0.4533(9) 0.8811(6) 0.105(3) Uani d . 1 . . C H23A 1.0976 0.5252 0.8473 0.158 Uiso calc R 1 . . H H23B 1.1491 0.3988 0.8488 0.158 Uiso calc R 1 . . H H23C 1.1613 0.4711 0.9374 0.158 Uiso calc R 1 . . H C1' 0.7533(4) 0.6423(5) 0.4439(4) 0.0415(13) Uani d . 1 . . C H1'A 0.6954 0.6744 0.4034 0.050 Uiso calc R 1 . . H C2' 0.8464(4) 0.6978(5) 0.4557(4) 0.0418(13) Uani d . 1 . . C H2'A 0.8508 0.7676 0.4245 0.050 Uiso calc R 1 . . H C3' 0.9417(4) 0.6531(5) 0.5158(4) 0.0447(14) Uani d . 1 . . C C4' 0.9288(4) 0.5461(5) 0.5654(4) 0.0463(14) Uani d . 1 . . C H4'A 0.9883 0.5154 0.6049 0.056 Uiso calc R 1 . . H C5' 0.8356(4) 0.4905(5) 0.5567(4) 0.0423(13) Uani d . 1 . . C C6' 0.8237(4) 0.3844(6) 0.6126(4) 0.0560(16) Uani d . 1 . . C H6'A 0.8915 0.3674 0.6531 0.067 Uiso calc R 1 . . H H6'B 0.8037 0.3158 0.5745 0.067 Uiso calc R 1 . . H C7' 0.7379(4) 0.4076(5) 0.6660(4) 0.0519(16) Uani d . 1 . . C H7'A 0.7627 0.4690 0.7098 0.062 Uiso calc R 1 . . H H7'B 0.7266 0.3359 0.6975 0.062 Uiso calc R 1 . . H C8' 0.6305(4) 0.4467(5) 0.6043(4) 0.0393(12) Uani d . 1 . . C H8'A 0.6028 0.3799 0.5652 0.047 Uiso calc R 1 . . H C9' 0.6478(4) 0.5516(4) 0.5458(3) 0.0350(12) Uani d . 1 . . C C10' 0.7354(4) 0.5306(4) 0.4919(3) 0.0371(12) Uani d . 1 . . C C11' 0.5381(4) 0.5986(5) 0.4926(4) 0.0395(13) Uani d . 1 . . C C12' 0.4570(4) 0.6279(5) 0.5476(4) 0.0390(13) Uani d . 1 . . C H12C 0.3900 0.6525 0.5090 0.047 Uiso calc R 1 . . H H12D 0.4832 0.6921 0.5885 0.047 Uiso calc R 1 . . H C13' 0.4398(4) 0.5166(5) 0.5992(3) 0.0390(13) Uani d . 1 . . C C14' 0.5472(4) 0.4782(5) 0.6580(3) 0.0393(12) Uani d . 1 . . C H14B 0.5753 0.5471 0.6946 0.047 Uiso calc R 1 . . H C15' 0.5197(4) 0.3859(6) 0.7213(4) 0.0524(15) Uani d . 1 . . C H15C 0.5729 0.3850 0.7770 0.063 Uiso calc R 1 . . H H15D 0.5153 0.3074 0.6950 0.063 Uiso calc R 1 . . H C16' 0.4085(4) 0.4258(6) 0.7367(4) 0.0523(15) Uani d . 1 . . C H16B 0.3570 0.3617 0.7168 0.063 Uiso calc R 1 . . H C17' 0.3754(4) 0.5346(5) 0.6739(4) 0.0428(13) Uani d . 1 . . C H17B 0.4030 0.6061 0.7074 0.051 Uiso calc R 1 . . H C18' 0.3855(4) 0.4203(5) 0.5334(4) 0.0508(15) Uani d . 1 . . C H18D 0.4256 0.4088 0.4885 0.076 Uiso calc R 1 . . H H18E 0.3141 0.4450 0.5060 0.076 Uiso calc R 1 . . H H18F 0.3828 0.3473 0.5649 0.076 Uiso calc R 1 . . H C19' 0.7004(5) 0.4331(5) 0.4199(4) 0.0564(16) Uani d . 1 . . C H19D 0.7554 0.4222 0.3873 0.085 Uiso calc R 1 . . H H19E 0.6353 0.4569 0.3797 0.085 Uiso calc R 1 . . H H19F 0.6889 0.3598 0.4482 0.085 Uiso calc R 1 . . H C20' 0.2575(4) 0.5490(6) 0.6421(4) 0.0503(15) Uani d . 1 . . C C21' 0.4088(5) 0.4540(8) 0.8326(4) 0.076(2) Uani d . 1 . . C H21D 0.3385 0.4785 0.8371 0.114 Uiso calc R 1 . . H H21E 0.4588 0.5167 0.8531 0.114 Uiso calc R 1 . . H H21F 0.4293 0.3846 0.8685 0.114 Uiso calc R 1 . . H C22' 0.7586(7) 0.2860(9) 0.9620(5) 0.081(2) Uani d . 1 . . C C23' 0.6602(7) 0.2464(10) 0.9900(6) 0.110(3) Uani d . 1 . . C H23D 0.6756 0.1760 1.0257 0.165 Uiso calc R 1 . . H H23E 0.6050 0.2297 0.9383 0.165 Uiso calc R 1 . . H H23F 0.6366 0.3080 1.0242 0.165 Uiso calc R 1 . . H O5 0.9290(5) 0.4418(8) 0.8647(6) 0.160(4) Uani d . 1 . . O O6 1.0254(5) 0.3034(6) 0.9404(4) 0.1044(19) Uani d . 1 . . O H6C 0.9678 0.2845 0.9511 0.157 Uiso calc R 1 . . H O5' 0.8425(5) 0.2273(5) 0.9814(4) 0.0943(17) Uani d . 1 . . O O6' 0.7506(5) 0.3789(8) 0.9139(6) 0.152(3) Uani d . 1 . . O H6'C 0.8083 0.3929 0.9015 0.227 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0469(18) 0.066(2) 0.061(2) 0.0075(17) 0.0140(16) 0.0117(19) F1' 0.0373(16) 0.0326(16) 0.0571(18) -0.0012(14) 0.0163(14) -0.0086(15) O1 0.043(2) 0.080(3) 0.094(3) 0.008(2) 0.010(2) 0.018(3) O2 0.051(3) 0.065(3) 0.121(4) -0.019(2) 0.030(3) -0.041(3) O3 0.047(3) 0.074(3) 0.126(4) 0.013(3) 0.015(3) 0.005(3) O4 0.041(2) 0.087(4) 0.104(4) 0.000(3) 0.015(2) 0.033(3) O1' 0.036(2) 0.046(3) 0.083(3) -0.0012(19) 0.017(2) 0.003(2) O2' 0.043(2) 0.072(3) 0.051(3) 0.004(2) 0.0054(19) 0.007(2) O3' 0.037(2) 0.076(3) 0.119(4) -0.005(2) 0.020(2) 0.027(3) O4' 0.038(2) 0.056(3) 0.119(4) 0.001(2) 0.023(2) 0.029(3) C1 0.056(4) 0.038(4) 0.086(5) -0.003(3) 0.034(3) -0.010(3) C2 0.051(4) 0.056(4) 0.084(5) 0.001(3) 0.036(3) 0.003(4) C3 0.046(4) 0.063(4) 0.055(4) -0.003(3) 0.017(3) 0.009(3) C4 0.038(3) 0.070(4) 0.066(4) -0.016(3) 0.023(3) -0.011(4) C5 0.045(3) 0.051(4) 0.057(4) -0.008(3) 0.027(3) -0.005(3) C6 0.048(3) 0.049(4) 0.067(4) -0.008(3) 0.023(3) -0.006(3) C7 0.040(3) 0.054(4) 0.068(4) -0.010(3) 0.018(3) -0.012(3) C8 0.039(3) 0.038(3) 0.047(3) -0.006(3) 0.013(2) 0.000(3) C9 0.035(3) 0.040(3) 0.050(3) 0.000(3) 0.010(2) 0.001(3) C10 0.038(3) 0.049(4) 0.059(4) -0.009(3) 0.019(3) -0.007(3) C11 0.037(3) 0.044(4) 0.083(5) 0.000(3) 0.018(3) 0.003(4) C12 0.039(3) 0.043(3) 0.080(4) -0.002(3) 0.022(3) 0.009(3) C13 0.035(3) 0.052(4) 0.040(3) 0.002(3) 0.013(2) 0.007(3) C14 0.036(3) 0.048(3) 0.042(3) 0.000(3) 0.010(2) 0.002(3) C15 0.048(3) 0.056(4) 0.060(4) -0.006(3) 0.016(3) -0.014(3) C16 0.047(3) 0.073(5) 0.057(4) 0.008(3) 0.018(3) -0.009(4) C17 0.042(3) 0.063(4) 0.051(4) 0.004(3) 0.011(3) 0.004(3) C18 0.048(3) 0.052(4) 0.050(3) -0.005(3) 0.007(3) -0.001(3) C19 0.060(4) 0.069(5) 0.057(4) -0.015(3) 0.024(3) -0.018(4) C20 0.034(3) 0.074(5) 0.070(4) 0.005(3) 0.022(3) 0.010(4) C21 0.103(6) 0.106(7) 0.075(5) -0.005(5) 0.042(5) -0.026(5) C22 0.066(5) 0.096(7) 0.077(5) 0.004(5) 0.007(4) 0.017(5) C23 0.091(6) 0.105(7) 0.124(7) -0.010(6) 0.030(5) 0.010(6) C1' 0.040(3) 0.038(3) 0.050(3) 0.008(3) 0.016(2) 0.001(3) C2' 0.037(3) 0.034(3) 0.057(3) 0.001(3) 0.014(3) -0.002(3) C3' 0.044(3) 0.043(3) 0.051(3) 0.007(3) 0.021(3) -0.005(3) C4' 0.037(3) 0.041(3) 0.063(4) 0.009(3) 0.014(3) 0.007(3) C5' 0.035(3) 0.035(3) 0.063(3) 0.012(3) 0.023(3) 0.001(3) C6' 0.044(3) 0.048(4) 0.081(4) 0.019(3) 0.025(3) 0.023(3) C7' 0.041(3) 0.047(4) 0.071(4) 0.012(3) 0.019(3) 0.016(3) C8' 0.033(3) 0.030(3) 0.059(3) 0.005(2) 0.018(2) -0.001(3) C9' 0.031(3) 0.028(3) 0.045(3) 0.003(2) 0.006(2) -0.005(3) C10' 0.035(3) 0.027(3) 0.051(3) 0.006(2) 0.014(2) 0.001(3) C11' 0.032(3) 0.037(3) 0.049(4) -0.002(2) 0.007(3) 0.009(3) C12' 0.034(3) 0.031(3) 0.053(3) 0.003(2) 0.011(2) -0.001(3) C13' 0.034(3) 0.034(3) 0.049(3) -0.002(2) 0.010(2) 0.000(3) C14' 0.034(3) 0.038(3) 0.047(3) -0.004(2) 0.012(2) 0.000(3) C15' 0.055(3) 0.055(4) 0.050(3) 0.007(3) 0.017(3) 0.012(3) C16' 0.041(3) 0.060(4) 0.060(4) -0.006(3) 0.020(3) 0.007(3) C17' 0.030(3) 0.044(3) 0.055(3) -0.005(3) 0.012(2) -0.003(3) C18' 0.044(3) 0.044(4) 0.064(4) -0.006(3) 0.012(3) -0.006(3) C19' 0.064(4) 0.044(4) 0.068(4) -0.008(3) 0.029(3) -0.015(3) C20' 0.035(3) 0.049(4) 0.074(4) -0.005(3) 0.026(3) -0.006(4) C21' 0.065(4) 0.102(6) 0.066(4) -0.004(4) 0.027(4) 0.005(4) C22' 0.079(6) 0.094(7) 0.067(5) 0.002(5) 0.009(4) -0.002(5) C23' 0.093(6) 0.144(9) 0.106(7) -0.012(7) 0.049(5) -0.012(7) O5 0.080(4) 0.169(7) 0.218(8) 0.018(5) 0.006(5) 0.111(7) O6 0.094(4) 0.104(5) 0.113(4) 0.000(4) 0.019(3) 0.027(4) O5' 0.081(4) 0.084(4) 0.110(4) -0.001(3) 0.003(3) 0.007(3) O6' 0.085(4) 0.151(7) 0.211(8) 0.019(5) 0.016(5) 0.083(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 C9 . 1.419(6) ? F1' C9' . 1.424(6) ? O1 C3 . 1.235(7) ? O2 C11 . 1.227(7) ? O3 C20 . 1.197(7) ? O4 C20 . 1.332(8) ? O4 H4B . 0.8200 ? O1' C3' . 1.241(6) ? O2' C11' . 1.202(6) ? O3' C20' . 1.208(7) ? O4' C20' . 1.330(7) ? O4' H4'B . 0.8200 ? C1 C2 . 1.306(8) ? C1 C10 . 1.511(9) ? C1 H1A . 0.9300 ? C2 C3 . 1.442(9) ? C2 H2A . 0.9300 ? C3 C4 . 1.471(10) ? C4 C5 . 1.324(8) ? C4 H4A . 0.9300 ? C5 C6 . 1.488(9) ? C5 C10 . 1.522(8) ? C6 C7 . 1.536(8) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 C8 . 1.530(7) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C14 . 1.523(7) ? C8 C9 . 1.546(8) ? C8 H8A . 0.9800 ? C9 C11 . 1.544(8) ? C9 C10 . 1.563(7) ? C10 C19 . 1.559(8) ? C11 C12 . 1.512(8) ? C12 C13 . 1.555(8) ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? C13 C14 . 1.543(7) ? C13 C18 . 1.545(7) ? C13 C17 . 1.546(8) ? C14 C15 . 1.517(8) ? C14 H14A . 0.9800 ? C15 C16 . 1.545(8) ? C15 H15A . 0.9700 ? C15 H15B . 0.9700 ? C16 C17 . 1.538(9) ? C16 C21 . 1.543(9) ? C16 H16A . 0.9800 ? C17 C20 . 1.495(8) ? C17 H17A . 0.9800 ? C18 H18A . 0.9600 ? C18 H18B . 0.9600 ? C18 H18C . 0.9600 ? C19 H19A . 0.9600 ? C19 H19B . 0.9600 ? C19 H19C . 0.9600 ? C21 H21A . 0.9600 ? C21 H21B . 0.9600 ? C21 H21C . 0.9600 ? C22 O5 . 1.196(9) ? C22 O6 . 1.269(10) ? C22 C23 . 1.483(11) ? C23 H23A . 0.9600 ? C23 H23B . 0.9600 ? C23 H23C . 0.9600 ? C1' C2' . 1.324(7) ? C1' C10' . 1.503(8) ? C1' H1'A . 0.9300 ? C2' C3' . 1.450(7) ? C2' H2'A . 0.9300 ? C3' C4' . 1.457(8) ? C4' C5' . 1.330(7) ? C4' H4'A . 0.9300 ? C5' C6' . 1.501(8) ? C5' C10' . 1.511(7) ? C6' C7' . 1.536(7) ? C6' H6'A . 0.9700 ? C6' H6'B . 0.9700 ? C7' C8' . 1.553(7) ? C7' H7'A . 0.9700 ? C7' H7'B . 0.9700 ? C8' C14' . 1.532(7) ? C8' C9' . 1.534(7) ? C8' H8'A . 0.9800 ? C9' C11' . 1.555(7) ? C9' C10' . 1.556(7) ? C10' C19' . 1.555(8) ? C11' C12' . 1.517(7) ? C12' C13' . 1.526(8) ? C12' H12C . 0.9700 ? C12' H12D . 0.9700 ? C13' C14' . 1.533(7) ? C13' C18' . 1.541(7) ? C13' C17' . 1.572(7) ? C14' C15' . 1.520(8) ? C14' H14B . 0.9800 ? C15' C16' . 1.563(7) ? C15' H15C . 0.9700 ? C15' H15D . 0.9700 ? C16' C21' . 1.511(8) ? C16' C17' . 1.560(8) ? C16' H16B . 0.9800 ? C17' C20' . 1.491(7) ? C17' H17B . 0.9800 ? C18' H18D . 0.9600 ? C18' H18E . 0.9600 ? C18' H18F . 0.9600 ? C19' H19D . 0.9600 ? C19' H19E . 0.9600 ? C19' H19F . 0.9600 ? C21' H21D . 0.9600 ? C21' H21E . 0.9600 ? C21' H21F . 0.9600 ? C22' O5' . 1.241(10) ? C22' O6' . 1.275(11) ? C22' C23' . 1.490(12) ? C23' H23D . 0.9600 ? C23' H23E . 0.9600 ? C23' H23F . 0.9600 ? O6 H6C . 0.8200 ? O6' H6'C . 0.8200 ?