data_2010722 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 358 _journal_page_last 359 _publ_section_title ; (1S,4R,5R,6R)-[6-(methoxycarbonyl)-2-(pivaloyloxymethyl)-4- (pivaloyloxy)bicyclo[3.1.0]hex-2-en-1-yl]-1-carboxylic acid ; loop_ _publ_author_name "Chiaroni, Ang\`ele" "Riche, Claude" "Cachet, Xavier" "Deguin, Brigitte" "Koch, Michel" "Tillequin, Fran\,cois" _chemical_formula_sum 'C20 H28 O8' _chemical_formula_weight 396.42 _chemical_melting_point '128.2_C' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.869(2) _cell_length_b 9.836(2) _cell_length_c 12.225(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.40(3) _cell_angle_gamma 90.00 _cell_volume 1066.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.235 _diffrn_ambient_temperature 293(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 -.0911(2) .0373(2) .77730(15) .0374(4) Uani d . 1 . C C2 -.0441(2) .1769(2) .8151(2) .0412(4) Uani d . 1 . C C3 -.0776(2) .1960(2) .9188(2) .0489(5) Uani d . 1 . C H3 -.0574(2) .2762(2) .9567(2) .059 Uiso calc R 1 . H C4 -.1517(2) .0748(2) .9690(2) .0450(4) Uani d . 1 . C H4 -.0922(2) .0426(2) 1.0324(2) .054 Uiso calc R 1 . H C5 -.1520(2) -.0301(2) .87907(15) .0400(4) Uani d . 1 . C H5 -.2387(2) -.0914(2) .87115(15) .048 Uiso calc R 1 . H C6 -.0038(2) -.0753(2) .83816(14) .0382(4) Uani d . 1 . C H6 .0841(2) -.0445(2) .88148(14) .046 Uiso calc R 1 . H C7 -.1508(2) .0184(2) .6646(2) .0431(4) Uani d . 1 . C O8 -.1896(2) -.1086(2) .64240(13) .0600(4) Uani d . 1 . O HO8 -.2194(2) -.1141(2) .57851(13) .081(9) Uiso calc R 1 . H O9 -.1629(3) .1081(2) .59943(14) .0787(6) Uani d . 1 . O C10 .0429(2) .2694(2) .7438(2) .0479(5) Uani d . 1 . C H10A -.0197(2) .3024(2) .6833(2) .058 Uiso calc R 1 . H H10B .0815(2) .3465(2) .7852(2) .058 Uiso calc R 1 . H O11 .1649(2) .18663(15) .70465(12) .0515(4) Uani d . 1 . O C12 .2374(2) .2267(2) .6167(2) .0479(5) Uani d . 1 . C O13 .2115(2) .3354(2) .57380(14) .0696(5) Uani d . 1 . O C14 .3456(3) .1210(3) .5766(2) .0584(6) Uani d . 1 . C C15 .4674(4) .1887(5) .5104(3) .1082(13) Uani d . 1 . C H15A .5361(4) .1210(5) .4849(3) .162 Uiso calc R 1 . H H15B .5213(4) .2531(5) .5556(3) .162 Uiso calc R 1 . H H15C .4218(4) .2349(5) .4488(3) .162 Uiso calc R 1 . H C16 .4187(3) .0424(4) .6714(3) .0842(9) Uani d . 1 . C H16A .4868(3) -.0241(4) .6432(3) .126 Uiso calc R 1 . H H16B .3419(3) -.0024(4) .7120(3) .126 Uiso calc R 1 . H H16C .4732(3) .1042(4) .7185(3) .126 Uiso calc R 1 . H C17 .2516(4) .0235(4) .5048(3) .1015(11) Uani d . 1 . C H17A .3157(4) -.0464(4) .4769(3) .152 Uiso calc R 1 . H H17B .2059(4) .0728(4) .4449(3) .152 Uiso calc R 1 . H H17C .1743(4) -.0171(4) .5476(3) .152 Uiso calc R 1 . H O18 -.3029(2) .1104(2) 1.00098(12) .0512(4) Uani d . 1 . O C19 -.3685(2) .0229(2) 1.0707(2) .0471(5) Uani d . 1 . C O20 -.3041(2) -.0782(2) 1.1025(2) .0702(5) Uani d . 1 . O C21 -.5253(2) .0666(2) 1.1027(2) .0529(5) Uani d . 1 . C C22 -.5878(4) -.0405(4) 1.1798(4) .1093(14) Uani d . 1 . C H22A -.5224(4) -.0484(4) 1.2432(4) .164 Uiso calc R 1 . H H22B -.5937(4) -.1264(4) 1.1427(4) .164 Uiso calc R 1 . H H22C -.6867(4) -.0138(4) 1.2018(4) .164 Uiso calc R 1 . H C23 -.5132(3) .2031(3) 1.1615(3) .0782(8) Uani d . 1 . C H23A -.4494(3) .1937(3) 1.2257(3) .117 Uiso calc R 1 . H H23B -.6117(3) .2322(3) 1.1824(3) .117 Uiso calc R 1 . H H23C -.4708(3) .2694(3) 1.1135(3) .117 Uiso calc R 1 . H C24 -.6253(3) .0817(5) 1.0022(3) .0954(11) Uani d . 1 . C H24A -.7242(3) .1093(5) 1.0233(3) .143 Uiso calc R 1 . H H24B -.6317(3) -.0038(5) .9644(3) .143 Uiso calc R 1 . H H24C -.5837(3) .1491(5) .9548(3) .143 Uiso calc R 1 . H C25 .0095(2) -.2157(2) .7905(2) .0409(4) Uani d . 1 . C O26 -.0663(2) -.3108(2) .81357(14) .0623(4) Uani d . 1 . O O27 .1220(2) -.21990(15) .72120(13) .0542(4) Uani d . 1 . O C28 .1418(3) -.3480(3) .6647(2) .0694(7) Uani d . 1 . C H28A .2255(3) -.3410(3) .6167(2) .104 Uiso calc R 1 . H H28B .0519(3) -.3691(3) .6228(2) .104 Uiso calc R 1 . H H28C .1612(3) -.4188(3) .7173(2) .104 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 C1 .0353(8) .0411(9) .0359(9) -.0014(7) .0038(7) -.0029(7) C2 .0426(9) .0392(9) .0418(9) -.0018(7) .0022(8) -.0028(8) C3 .0555(11) .0464(10) .0450(11) -.0060(9) .0065(9) -.0111(9) C4 .0444(10) .0540(11) .0369(9) .0022(8) .0078(8) -.0038(8) C5 .0377(9) .0451(9) .0376(10) -.0028(7) .0059(7) -.0031(8) C6 .0383(8) .0415(9) .0348(9) -.0004(7) .0020(7) .0000(7) C7 .0411(9) .0497(10) .0385(10) -.0012(8) -.0014(8) -.0036(8) O8 .0753(10) .0555(9) .0483(8) -.0044(8) -.0158(7) -.0104(7) O9 .117(2) .0672(10) .0506(9) -.0123(11) -.0280(10) .0097(9) C10 .0507(10) .0422(10) .0514(11) -.0031(9) .0081(9) .0003(9) O11 .0498(7) .0501(7) .0551(8) .0027(6) .0131(6) .0135(7) C12 .0482(10) .0547(11) .0409(10) -.0048(9) .0036(9) .0094(9) O13 .0930(12) .0599(9) .0567(9) .0122(9) .0173(9) .0224(8) C14 .0467(11) .0698(14) .0593(13) .0076(10) .0146(10) .0169(11) C15 .071(2) .135(3) .120(3) .025(2) .047(2) .057(3) C16 .068(2) .100(2) .085(2) .028(2) .0116(14) .032(2) C17 .097(2) .107(2) .100(2) .031(2) .003(2) -.040(2) O18 .0525(8) .0549(8) .0469(8) .0101(6) .0170(6) .0025(6) C19 .0481(10) .0538(11) .0397(10) .0046(9) .0076(8) -.0018(8) O20 .0585(9) .0678(10) .0848(12) .0141(9) .0148(8) .0243(10) C21 .0484(11) .0612(12) .0497(11) .0058(9) .0136(9) -.0025(10) C22 .087(2) .093(2) .150(3) .016(2) .067(2) .034(2) C23 .0684(15) .079(2) .088(2) .0189(14) .0143(14) -.023(2) C24 .0542(14) .149(3) .083(2) .018(2) -.0076(13) -.030(2) C25 .0419(9) .0436(10) .0373(9) .0018(8) .0022(8) -.0004(8) O26 .0705(10) .0454(8) .0718(10) -.0101(7) .0190(8) -.0018(7) O27 .0510(8) .0507(8) .0617(9) -.0008(6) .0189(7) -.0122(7) C28 .0683(14) .066(2) .074(2) .0077(12) .0148(13) -.0267(13) 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 C1 C7 . 1.476(3) ? C1 C2 . 1.504(3) ? C1 C5 . 1.520(3) ? C1 C6 . 1.533(3) ? C2 C3 . 1.323(3) ? C2 C10 . 1.488(3) ? C3 C4 . 1.499(3) ? C4 O18 . 1.450(2) ? C4 C5 . 1.507(3) ? C5 C6 . 1.486(3) ? C6 C25 . 1.505(3) ? C7 O9 . 1.192(3) ? C7 O8 . 1.323(3) ? C10 O11 . 1.445(2) ? O11 C12 . 1.326(3) ? C12 O13 . 1.210(3) ? C12 C14 . 1.505(3) ? C14 C15 . 1.519(4) ? C14 C16 . 1.525(4) ? C14 C17 . 1.533(5) ? O18 C19 . 1.353(3) ? C19 O20 . 1.206(3) ? C19 C21 . 1.516(3) ? C21 C24 . 1.505(4) ? C21 C22 . 1.526(4) ? C21 C23 . 1.526(4) ? C25 O26 . 1.190(2) ? C25 O27 . 1.325(2) ? O27 C28 . 1.449(3) ?