#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200693.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_2200693 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o1196 _journal_page_last o1197 _publ_section_title ; (2S)-1-(4-Fluorophenyl)-2-hydroxy-2-[(2S,5R)-5-(1-hydroxy-1-methylethyl)- tetrahydrofuran-2-yl]ethanone ; loop_ _publ_author_name 'Light, Mark E.' 'Hursthouse, Michael B.' _chemical_formula_moiety 'C15 H19 F O4' _chemical_formula_sum 'C15 H19 F O4' _chemical_formula_iupac 'C15 H19 F O4' _chemical_formula_weight 282.30 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' 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 10.973(2) _cell_length_b 12.764(3) _cell_length_c 20.721(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2902.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.292 _diffrn_ambient_temperature 150(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 H03 .281(5) .455(3) .498(3) .12(2) Uiso d . 1 . . H H05 .378(3) .433(3) .606(2) .059(14) Uiso d . 1 . . H H07 .170(4) .317(3) .524(3) .12(2) Uiso d . 1 . . H H01 .101(8) .467(7) .390(5) .29(5) Uiso d . 1 . . H F1 .9054(2) .6714(2) .35904(15) .1113(10) Uani d . 1 . . F O1 .0690(3) .4227(3) .35724(17) .0885(9) Uani d . 1 . . O O2 .3240(2) .43508(15) .37016(13) .0562(7) Uani d . 1 . . O O3 .3327(2) .4025(2) .50992(14) .0688(8) Uani d . 1 . . O O4 .3905(2) .5942(2) .48140(15) .0830(9) Uani d . 1 . . O C1 .0825(4) .3644(3) .2500(2) .0832(14) Uani d . 1 . . C H1A .0055 .3993 .2395 .125 Uiso calc R 1 . . H H1B .0661 .2930 .2650 .125 Uiso calc R 1 . . H H1C .1341 .3618 .2114 .125 Uiso calc R 1 . . H C2 .1712(4) .5381(3) .2822(3) .0938(15) Uani d . 1 . . C H2A .0935 .5717 .2716 .141 Uiso calc R 1 . . H H2B .2241 .5383 .2441 .141 Uiso calc R 1 . . H H2C .2109 .5767 .3173 .141 Uiso calc R 1 . . H C3 .1483(3) .4259(3) .3033(2) .0599(10) Uani d . 1 . . C C4 .2670(3) .3738(2) .3201(2) .0574(10) Uani d . 1 . . C H4 .3209 .3735 .2812 .069 Uiso calc R 1 . . H C5 .2618(4) .2636(3) .3481(3) .0923(16) Uani d . 1 . . C H5A .1799 .2491 .3660 .111 Uiso calc R 1 . . H H5B .2798 .2110 .3143 .111 Uiso calc R 1 . . H C6 .3559(3) .2594(3) .4002(2) .0666(11) Uani d . 1 . . C H6A .4189 .2064 .3901 .080 Uiso calc R 1 . . H H6B .3181 .2418 .4422 .080 Uiso calc R 1 . . H C7 .4108(3) .3688(2) .40180(18) .0525(10) Uani d . 1 . . C H7 .4882 .3687 .3763 .063 Uiso calc R 1 . . H C8 .4357(3) .4150(3) .46785(19) .0528(9) Uani d . 1 . . C H8 .5066 .3773 .4872 .063 Uiso calc R 1 . . H C9 .4672(4) .5305(3) .4633(2) .0590(10) Uani d . 1 . . C C10 .5834(3) .5647(3) .43559(19) .0531(9) Uani d . 1 . . C C11 .6798(3) .4960(3) .42333(19) .0556(10) Uani d . 1 . . C H11 .6709 .4237 .4332 .067 Uiso calc R 1 . . H C12 .7878(4) .5316(3) .3971(2) .0651(11) Uani d . 1 . . C H12 .8528 .4847 .3880 .078 Uiso calc R 1 . . H C13 .7984(4) .6350(4) .3849(2) .0742(12) Uani d . 1 . . C C14 .7092(5) .7064(3) .3978(2) .0851(14) Uani d . 1 . . C H14 .7215 .7789 .3897 .102 Uiso calc R 1 . . H C15 .5991(4) .6701(3) .4233(2) .0715(12) Uani d . 1 . . C H15 .5350 .7180 .4322 .086 Uiso calc R 1 . . H F2 -.3763(2) .69292(18) .59889(14) .1072(10) Uani d . 1 . . F O5 .4228(3) .4280(2) .63817(17) .0687(8) Uani d . 1 . . O O6 .1594(2) .43280(16) .64255(12) .0544(7) Uani d . 1 . . O O7 .1263(3) .2666(2) .54482(15) .0730(9) Uani d . 1 . . O O8 .0838(2) .4567(2) .49763(14) .0752(8) Uani d . 1 . . O C16 .4304(4) .4763(3) .7483(2) .0838(13) Uani d . 1 . . C H16A .4471 .4031 .7596 .126 Uiso calc R 1 . . H H16B .3865 .5102 .7838 .126 Uiso calc R 1 . . H H16C .5075 .5131 .7407 .126 Uiso calc R 1 . . H C17 .3274(4) .5927(3) .6677(3) .0864(14) Uani d . 1 . . C H17A .2785 .5936 .6282 .130 Uiso calc R 1 . . H H17B .4047 .6292 .6601 .130 Uiso calc R 1 . . H H17C .2826 .6281 .7024 .130 Uiso calc R 1 . . H C18 .3527(3) .4802(3) .6872(2) .0569(10) Uani d . 1 . . C C19 .2337(3) .4215(2) .6987(2) .0542(9) Uani d . 1 . . C H19 .1907 .4527 .7367 .065 Uiso calc R 1 . . H C20 .2415(3) .3037(2) .7072(2) .0645(11) Uani d . 1 . . C H20A .3063 .2735 .6796 .077 Uiso calc R 1 . . H H20B .2579 .2850 .7527 .077 Uiso calc R 1 . . H C21 .1168(3) .2657(3) .6863(2) .0633(11) Uani d . 1 . . C H21A .0640 .2528 .7242 .076 Uiso calc R 1 . . H H21B .1234 .2003 .6609 .076 Uiso calc R 1 . . H C22 .0659(3) .3547(2) .64493(19) .0538(9) Uani d . 1 . . C H22 -.0079 .3846 .6665 .065 Uiso calc R 1 . . H C23 .0346(3) .3272(3) .57498(19) .0567(10) Uani d . 1 . . C H23 -.0425 .2855 .5750 .068 Uiso calc R 1 . . H C24 .0111(3) .4291(3) .5388(2) .0541(10) Uani d . 1 . . C C25 -.0923(3) .4969(3) .55743(19) .0502(9) Uani d . 1 . . C C26 -.2003(3) .4575(3) .58240(19) .0580(10) Uani d . 1 . . C H26 -.2079 .3844 .5901 .070 Uiso calc R 1 . . H C27 -.2960(3) .5227(3) .5961(2) .0622(11) Uani d . 1 . . C H27 -.3703 .4957 .6127 .075 Uiso calc R 1 . . H C28 -.2819(4) .6274(3) .5853(2) .0682(12) Uani d . 1 . . C C29 -.1778(4) .6701(3) .5614(2) .0692(11) Uani d . 1 . . C H29 -.1707 .7436 .5551 .083 Uiso calc R 1 . . H C30 -.0824(3) .6037(3) .5466(2) .0630(11) Uani d . 1 . . C H30 -.0094 .6315 .5288 .076 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 .102(2) .120(2) .112(2) -.0515(16) .0059(18) .0066(18) O1 .0553(17) .139(3) .072(2) -.0022(17) .0102(18) -.010(2) O2 .0600(16) .0481(12) .0605(18) -.0021(12) -.0084(13) .0050(12) O3 .0618(18) .0861(19) .0585(19) .0050(15) .0154(16) .0016(15) O4 .0786(19) .0768(17) .094(3) .0223(15) .0129(18) -.0191(16) C1 .077(3) .100(3) .073(4) -.010(2) -.012(3) -.021(3) C2 .120(4) .069(3) .093(4) .001(2) -.032(3) .015(2) C3 .056(2) .077(3) .047(3) -.0027(19) -.001(2) -.003(2) C4 .057(2) .060(2) .055(3) -.0079(18) -.002(2) -.0071(19) C5 .103(4) .057(2) .117(4) -.009(2) -.036(3) .003(2) C6 .068(3) .051(2) .081(3) .0061(17) .007(3) .002(2) C7 .046(2) .059(2) .053(3) .0054(17) .007(2) -.0034(18) C8 .043(2) .065(2) .050(3) .0081(17) .008(2) .0024(19) C9 .058(3) .062(2) .057(3) .009(2) -.005(2) -.0032(19) C10 .061(2) .046(2) .052(3) .0007(17) -.010(2) .0000(17) C11 .054(2) .053(2) .060(3) -.0028(18) -.010(2) -.0045(18) C12 .059(3) .068(2) .068(3) -.0102(19) -.002(2) -.004(2) C13 .066(3) .089(3) .068(3) -.028(3) -.006(2) .003(2) C14 .110(4) .059(3) .086(4) -.015(3) -.015(3) .009(2) C15 .081(3) .066(3) .067(3) .007(2) -.011(3) .002(2) F2 .0923(17) .0889(16) .140(3) .0324(14) .0103(19) -.0046(16) O5 .0529(17) .095(2) .058(2) .0003(14) .0054(18) -.0081(17) O6 .0567(15) .0523(13) .0542(18) -.0049(11) -.0057(14) .0066(11) O7 .0700(19) .0668(17) .082(2) .0047(15) .0121(18) -.0201(17) O8 .0657(19) .103(2) .057(2) .0025(15) .0132(16) .0101(16) C16 .066(3) .120(3) .065(3) -.019(2) -.012(3) -.022(3) C17 .094(3) .063(3) .102(4) -.021(2) .001(3) -.007(2) C18 .053(2) .066(2) .052(3) -.0069(18) .000(2) -.015(2) C19 .055(2) .057(2) .051(3) -.0015(17) -.003(2) -.0017(18) C20 .068(3) .067(2) .058(3) .0040(19) -.009(2) .010(2) C21 .060(3) .055(2) .075(3) -.0068(17) -.003(2) .007(2) C22 .049(2) .052(2) .060(3) -.0081(17) .004(2) -.0005(19) C23 .046(2) .064(2) .059(3) -.0068(17) .002(2) -.013(2) C24 .048(2) .068(2) .046(3) -.0114(18) -.002(2) -.0056(19) C25 .046(2) .055(2) .050(2) -.0055(16) -.002(2) .0001(17) C26 .052(2) .064(2) .058(3) -.0017(18) .003(2) .0060(19) C27 .049(2) .074(3) .064(3) .0006(19) .003(2) .007(2) C28 .061(3) .073(3) .071(3) .010(2) .000(2) -.003(2) C29 .077(3) .061(2) .070(3) -.002(2) -.002(3) .007(2) C30 .057(2) .071(3) .061(3) -.009(2) .001(2) .004(2) 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 C13 . 1.372(5) no O1 C3 . 1.417(5) no O1 H01 . .95(10) no O2 C7 . 1.433(4) no O2 C4 . 1.441(4) no O3 C8 . 1.436(4) no O3 H03 . .91(4) no O4 C9 . 1.229(4) no C1 C3 . 1.536(5) no C1 H1A . .9800 no C1 H1B . .9800 no C1 H1C . .9800 no C2 C3 . 1.518(5) no C2 H2A . .9800 no C2 H2B . .9800 no C2 H2C . .9800 no C3 C4 . 1.503(5) no C4 C5 . 1.522(4) no C4 H4 . 1.0000 no C5 C6 . 1.495(5) no C5 H5A . .9900 no C5 H5B . .9900 no C6 C7 . 1.521(4) no C6 H6A . .9900 no C6 H6B . .9900 no C7 C8 . 1.515(5) no C7 H7 . 1.0000 no C8 C9 . 1.517(5) no C8 H8 . 1.0000 no C9 C10 . 1.465(5) no C10 C15 . 1.380(5) no C10 C11 . 1.396(5) no C11 C12 . 1.381(5) no C11 H11 . .9500 no C12 C13 . 1.349(5) no C12 H12 . .9500 no C13 C14 . 1.364(6) no C14 C15 . 1.397(6) no C14 H14 . .9500 no C15 H15 . .9500 no F2 C28 . 1.360(4) no O5 C18 . 1.437(4) no O5 H05 . .83(4) no O6 C19 . 1.429(4) no O6 C22 . 1.431(3) no O7 C23 . 1.414(4) no O7 H07 . .91(5) no O8 C24 . 1.219(4) no C16 C18 . 1.528(5) no C16 H16A . .9800 no C16 H16B . .9800 no C16 H16C . .9800 no C17 C18 . 1.518(5) no C17 H17A . .9800 no C17 H17B . .9800 no C17 H17C . .9800 no C18 C19 . 1.524(5) no C19 C20 . 1.516(4) no C19 H19 . 1.0000 no C20 C21 . 1.515(5) no C20 H20A . .9900 no C20 H20B . .9900 no C21 C22 . 1.528(5) no C21 H21A . .9900 no C21 H21B . .9900 no C22 C23 . 1.530(5) no C22 H22 . 1.0000 no C23 C24 . 1.524(5) no C23 H23 . 1.0000 no C24 C25 . 1.478(5) no C25 C30 . 1.386(4) no C25 C26 . 1.388(4) no C26 C27 . 1.370(5) no C26 H26 . .9500 no C27 C28 . 1.364(5) no C27 H27 . .9500 no C28 C29 . 1.359(5) no C29 C30 . 1.381(5) no C29 H29 . .9500 no C30 H30 . .9500 no