#------------------------------------------------------------------------------ #$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $ #$Revision: 481 $ #$URL: svn://www.crystallography.net/cod/cif/2/2007008.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_2007008 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1998 _journal_volume 54 _journal_page_first 256 _journal_page_last 261 _publ_section_title ; Crystallographic Evidence of [1,5]Prototropic Shifts occuring upon Transannular Diels--Alder Reaction of a 14-Membered Macrocycle leading to a 5\a-Steroid Skeleton ; loop_ _publ_author_name ' Drouin, Marc' 'Couturier, Michel' 'Deslongchamps, Pierre' _chemical_formula_sum 'C48 H60 O16' _chemical_formula_structural 'C24 H30 O8' _chemical_formula_iupac 'C24 H30 O8' _chemical_formula_weight 892.96 _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.9986(4) _cell_length_b 12.1754(6) _cell_length_c 53.584(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4566.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.299 _diffrn_ambient_temperature 293.0(10) _refine_ls_R_factor_obs .0631 _refine_ls_wR_factor_obs .1641 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 1.6707(6) 1.0466(3) 1.06456(6) .0570(9) Uani d . 1 . C H1A 1.6080 1.1166 1.0617 .068 Uiso calc . 1 . H H1B 1.7895 1.0610 1.0733 .068 Uiso calc . 1 . H C2 1.7162(6) .9943(4) 1.03936(6) .0619(9) Uani d . 1 . C H2A 1.7942 .9295 1.0421 .074 Uiso calc . 1 . H H2B 1.7905 1.0457 1.0295 .074 Uiso calc . 1 . H C3 1.5379(6) .9615(3) 1.02464(6) .0572(9) Uani d . 1 . C C4 1.4039(6) .8926(3) 1.04119(6) .0596(9) Uani d . 1 . C H4A 1.2853 .8791 1.0323 .071 Uiso calc . 1 . H H4B 1.4630 .8222 1.0447 .071 Uiso calc . 1 . H C5 1.3611(5) .9510(3) 1.06568(6) .0512(8) Uani d . 1 . C H5 1.3091 1.0230 1.0611 .061 Uiso calc . 1 . H C6 1.2081(6) .8950(3) 1.08040(6) .0566(9) Uani d . 1 . C H6 1.1179 .8532 1.0719 .068 Uiso calc . 1 . H C7 1.1951(6) .9021(3) 1.10488(6) .0562(9) Uani d . 1 . C H7 1.0926 .8680 1.1128 .067 Uiso calc . 1 . H C8 1.3367(5) .9622(3) 1.12056(6) .0478(7) Uani d . 1 . C H8 1.4171 .9079 1.1290 .057 Uiso calc . 1 . H C9 1.4671(5) 1.0362(3) 1.10463(5) .0457(7) Uani d . 1 . C H9 1.3834 1.0941 1.0981 .055 Uiso calc . 1 . H C10 1.5416(5) .9747(3) 1.08131(6) .0494(8) Uani d . 1 . C C11 1.6107(5) 1.0950(3) 1.12106(6) .0519(8) Uani d . 1 . C C12 1.5280(6) 1.1586(3) 1.14278(6) .0556(8) Uani d . 1 . C H12A 1.4631 1.2234 1.1366 .067 Uiso calc . 1 . H H12B 1.6309 1.1826 1.1536 .067 Uiso calc . 1 . H C13 1.3873(5) 1.0890(3) 1.15777(6) .0487(8) Uani d . 1 . C C14 1.2409(5) 1.0329(3) 1.14031(5) .0484(7) Uani d . 1 . C H14 1.1766 1.0924 1.1313 .058 Uiso calc . 1 . H C15 1.0927(6) .9860(4) 1.15838(6) .0607(9) Uani d . 1 . C H15A .9742 .9687 1.1499 .073 Uiso calc . 1 . H H15B 1.1401 .9206 1.1666 .073 Uiso calc . 1 . H C16 1.0658(6) 1.0801(4) 1.17683(7) .0669(10) Uani d . 1 . C H16A .9565 1.1246 1.1722 .080 Uiso calc . 1 . H H16B 1.0465 1.0520 1.1936 .080 Uiso calc . 1 . H C17 1.2492(6) 1.1471(3) 1.17542(6) .0600(9) Uani d . 1 . C C18 1.6469(6) .8699(3) 1.08896(7) .0610(9) Uani d . 1 . C H18A 1.7577 .8888 1.0986 .092 Uiso calc . 1 . H H18B 1.6855 .8305 1.0743 .092 Uiso calc . 1 . H H18C 1.5635 .8246 1.0988 .092 Uiso calc . 1 . H C19 1.4328(7) 1.0602(3) 1.01431(7) .0638(10) Uani d . 1 . C C20 1.4606(11) 1.2182(5) .98918(13) .135(3) Uani d . 1 . C H20A 1.5566 1.2606 .9808 .203 Uiso calc . 1 . H H20B 1.3962 1.2635 1.0012 .203 Uiso calc . 1 . H H20C 1.3698 1.1912 .9772 .203 Uiso calc . 1 . H C21 1.5909(7) .8886(3) 1.00242(7) .0631(10) Uani d . 1 . C C22 1.5003(9) .8317(4) .96203(7) .094(2) Uani d . 1 . C H22A 1.4073 .8494 .9495 .142 Uiso calc . 1 . H H22B 1.4849 .7565 .9670 .142 Uiso calc . 1 . H H22C 1.6263 .8422 .9554 .142 Uiso calc . 1 . H C23 1.4991(5) 1.0031(3) 1.17223(6) .0496(8) Uani d . 1 . C C24 1.5343(8) .9080(4) 1.20998(7) .0820(14) Uani d . 1 . C H24A 1.4838 .9076 1.2266 .123 Uiso calc . 1 . H H24B 1.6694 .9216 1.2106 .123 Uiso calc . 1 . H H24C 1.5112 .8381 1.2023 .123 Uiso calc . 1 . H O1 1.7837(4) 1.0970(2) 1.11729(5) .0662(7) Uani d . 1 . O O2 1.2784(5) 1.2350(2) 1.18541(5) .0830(9) Uani d . 1 . O O3 1.2646(5) 1.0785(3) 1.01660(6) .0825(9) Uani d . 1 . O O4 1.5497(5) 1.1264(3) 1.00181(6) .0894(10) Uani d . 1 . O O5 1.7186(6) .8236(3) 1.00236(6) .1027(12) Uani d . 1 . O O6 1.4735(5) .9026(2) .98341(5) .0774(8) Uani d . 1 . O O7 1.6277(4) .9494(3) 1.16360(5) .0705(7) Uani d . 1 . O O8 1.4421(4) .9934(2) 1.19565(4) .0652(7) Uani d . 1 . O C1' 1.4530(6) 1.4642(3) 1.14469(6) .0614(9) Uani d . 1 . C H1'1 1.5638 1.4587 1.1555 .074 Uiso calc . 1 . H H1'2 1.3823 1.3959 1.1460 .074 Uiso calc . 1 . H C2' 1.5203(7) 1.4788(3) 1.11774(7) .0696(11) Uani d . 1 . C H2'1 1.5907 1.4138 1.1127 .084 Uiso calc . 1 . H H2'2 1.6075 1.5407 1.1170 .084 Uiso calc . 1 . H C3' 1.3573(7) 1.4982(3) 1.09895(6) .0677(11) Uani d . 1 . C C4' 1.2278(7) 1.5904(3) 1.10855(6) .0636(10) Uani d . 1 . C H4'1 1.2974 1.6592 1.1082 .076 Uiso calc . 1 . H H4'2 1.1183 1.5975 1.0976 .076 Uiso calc . 1 . H C5' 1.1587(6) 1.5685(3) 1.13491(6) .0527(8) Uani d . 1 . C H5' 1.0975 1.4961 1.1345 .063 Uiso calc . 1 . H C6' 1.0085(5) 1.6473(3) 1.14384(6) .0555(8) Uani d . 1 . C H6' .9295 1.6801 1.1320 .067 Uiso calc . 1 . H C7' .9827(5) 1.6725(3) 1.16770(6) .0560(8) Uani d . 1 . C H7' .8848 1.7209 1.1718 .067 Uiso calc . 1 . H C8' 1.1027(5) 1.6273(3) 1.18835(6) .0482(7) Uani d . 1 . C H8' 1.1870 1.6861 1.1942 .058 Uiso calc . 1 . H C9' 1.2298(5) 1.5316(3) 1.17921(5) .0487(7) Uani d . 1 . C H9' 1.1405 1.4718 1.1755 .058 Uiso calc . 1 . H C10' 1.3261(5) 1.5587(3) 1.15379(6) .0501(8) Uani d . 1 . C C11' 1.3536(5) 1.4885(3) 1.20019(6) .0522(8) Uani d . 1 . C C12' 1.2444(5) 1.4515(3) 1.22307(6) .0518(8) Uani d . 1 . C H12C 1.3336 1.4321 1.2362 .062 Uiso calc . 1 . H H12D 1.1694 1.3869 1.2191 .062 Uiso calc . 1 . H C13' 1.1123(5) 1.5431(3) 1.23218(6) .0467(7) Uani d . 1 . C C14' .9862(5) 1.5866(3) 1.21067(5) .0477(7) Uani d . 1 . C H14' .9131 1.5233 1.2046 .057 Uiso calc . 1 . H C15' .8432(5) 1.6597(3) 1.22430(6) .0556(8) Uani d . 1 . C H15C .7314 1.6737 1.2141 .067 Uiso calc . 1 . H H15D .9006 1.7292 1.2290 .067 Uiso calc . 1 . H C16' .7920(5) 1.5917(3) 1.24723(7) .0584(9) Uani d . 1 . C H16C .7782 1.6384 1.2618 .070 Uiso calc . 1 . H H16D .6733 1.5522 1.2446 .070 Uiso calc . 1 . H C17' .9562(6) 1.5128(3) 1.25057(6) .0544(8) Uani d . 1 . C C18' 1.4407(6) 1.6650(3) 1.15576(7) .0604(9) Uani d . 1 . C H18D 1.3588 1.7231 1.1614 .091 Uiso calc . 1 . H H18E 1.4917 1.6836 1.1397 .091 Uiso calc . 1 . H H18F 1.5436 1.6552 1.1674 .091 Uiso calc . 1 . H C19' 1.4458(9) 1.5335(4) 1.07438(7) .0851(15) Uani d . 1 . C C20' 1.5106(11) 1.4962(7) 1.03265(8) .137(3) Uani d . 1 . C H20D 1.4837 1.4396 1.0207 .206 Uiso calc . 1 . H H20E 1.6464 1.5031 1.0347 .206 Uiso calc . 1 . H H20F 1.4590 1.5646 1.0269 .206 Uiso calc . 1 . H C21' 1.2462(10) 1.3913(3) 1.09500(7) .0790(14) Uani d . 1 . C C22' .9600(12) 1.3082(5) 1.08278(12) .132(3) Uani d . 1 . C H22D .8355 1.3280 1.0768 .198 Uiso calc . 1 . H H22E .9477 1.2690 1.0982 .198 Uiso calc . 1 . H H22F 1.0225 1.2623 1.0707 .198 Uiso calc . 1 . H C23' 1.2330(5) 1.6348(3) 1.24325(6) .0492(8) Uani d . 1 . C C24' 1.2863(7) 1.7482(4) 1.27846(8) .0783(12) Uani d . 1 . C H24D 1.2349 1.7605 1.2948 .117 Uiso calc . 1 . H H24E 1.2770 1.8145 1.2688 .117 Uiso calc . 1 . H H24F 1.4179 1.7268 1.2798 .117 Uiso calc . 1 . H O1' 1.5283(4) 1.4815(2) 1.19923(4) .0632(7) Uani d . 1 . O O2' .9595(4) 1.4329(2) 1.26435(5) .0701(7) Uani d . 1 . O O3' 1.5385(13) 1.6125(4) 1.07169(8) .219(4) Uani d . 1 . O O4' 1.4230(7) 1.4675(4) 1.05673(6) .1157(14) Uani d . 1 . O O5' 1.3119(9) 1.3028(3) 1.09881(8) .150(2) Uani d . 1 . O O6' 1.0711(6) 1.4058(3) 1.08671(6) .0912(10) Uani d . 1 . O O7' 1.1786(4) 1.6613(2) 1.26617(4) .0648(7) Uani d . 1 . O O8' 1.3670(4) 1.6769(2) 1.23289(5) .0662(7) Uani d . 1 . O 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 .056(2) .062(2) .053(2) -.009(2) .004(2) -.001(2) C2 .057(2) .077(2) .052(2) -.002(2) .005(2) -.002(2) C3 .067(2) .058(2) .046(2) .005(2) .003(2) .0001(14) C4 .069(2) .060(2) .050(2) -.007(2) .007(2) -.009(2) C5 .054(2) .054(2) .045(2) -.004(2) .0000(15) -.0026(14) C6 .053(2) .063(2) .054(2) -.010(2) .003(2) -.006(2) C7 .055(2) .059(2) .054(2) -.013(2) .005(2) -.0047(15) C8 .050(2) .047(2) .0462(15) -.004(2) -.0010(14) -.0050(13) C9 .047(2) .046(2) .0447(14) -.0029(15) -.0024(14) .0006(12) C10 .048(2) .050(2) .051(2) -.002(2) -.0013(14) -.0024(13) C11 .056(2) .049(2) .051(2) -.005(2) .000(2) .0064(14) C12 .067(2) .051(2) .048(2) -.007(2) -.003(2) .0013(14) C13 .055(2) .046(2) .0449(15) .002(2) -.0029(15) -.0005(13) C14 .050(2) .051(2) .0444(14) .002(2) -.0028(14) -.0002(13) C15 .052(2) .077(2) .054(2) .001(2) .003(2) -.003(2) C16 .061(2) .082(3) .059(2) .004(2) .011(2) -.012(2) C17 .069(3) .061(2) .050(2) .011(2) -.003(2) -.0067(15) C18 .062(2) .059(2) .062(2) .008(2) .004(2) -.002(2) C19 .076(3) .062(2) .053(2) -.005(2) .003(2) .003(2) C20 .139(6) .096(4) .171(6) -.032(4) -.051(5) .075(4) C21 .073(3) .068(2) .049(2) .009(2) .005(2) -.004(2) C22 .120(4) .106(4) .057(2) .002(4) .003(3) -.032(2) C23 .053(2) .050(2) .0453(14) -.001(2) .0000(14) .0036(13) C24 .107(4) .081(3) .057(2) .021(3) -.011(2) .020(2) O1 .053(2) .086(2) .0597(13) -.0153(15) .0012(12) -.0008(13) O2 .112(3) .063(2) .074(2) .009(2) .006(2) -.0214(14) O3 .084(2) .084(2) .080(2) .017(2) .002(2) .010(2) O4 .094(2) .073(2) .101(2) -.017(2) -.006(2) .027(2) O5 .113(3) .123(3) .072(2) .051(3) -.007(2) -.023(2) O6 .097(2) .082(2) .0539(13) .011(2) -.0107(15) -.0186(13) O7 .061(2) .085(2) .0653(15) .017(2) .0061(13) .0100(14) O8 .084(2) .0680(15) .0437(11) .0166(15) -.0007(12) .0083(11) C1' .071(3) .061(2) .052(2) .010(2) .004(2) -.004(2) C2' .084(3) .069(2) .055(2) .009(2) .011(2) -.006(2) C3' .103(3) .053(2) .046(2) .002(2) .010(2) .0014(15) C4' .088(3) .053(2) .050(2) .002(2) -.001(2) .0066(15) C5' .065(2) .050(2) .0430(15) -.003(2) -.004(2) -.0009(13) C6' .053(2) .060(2) .054(2) .002(2) -.005(2) .0058(15) C7' .055(2) .057(2) .056(2) .002(2) -.002(2) .0048(15) C8' .046(2) .048(2) .050(2) .0004(15) -.0054(14) .0035(13) C9' .050(2) .052(2) .0444(14) .003(2) -.0015(14) -.0004(13) C10' .052(2) .049(2) .049(2) .001(2) .0018(15) -.0026(13) C11' .050(2) .053(2) .053(2) .002(2) -.004(2) -.0051(14) C12' .058(2) .049(2) .0483(15) .006(2) -.002(2) -.0010(13) C13' .046(2) .046(2) .048(2) .0001(15) -.0009(13) -.0051(13) C14' .046(2) .052(2) .0448(15) .001(2) -.0016(14) .0009(13) C15' .051(2) .058(2) .058(2) .006(2) .002(2) .003(2) C16' .048(2) .070(2) .058(2) .007(2) .007(2) .005(2) C17' .060(2) .055(2) .049(2) -.004(2) -.001(2) .0050(14) C18' .062(2) .057(2) .062(2) -.008(2) .005(2) -.003(2) C19' .134(5) .065(2) .057(2) .002(3) .022(3) -.003(2) C20' .141(6) .216(7) .054(2) -.012(6) .036(3) -.010(4) C21' .135(5) .055(2) .047(2) .005(3) -.006(3) .002(2) C22' .159(6) .099(4) .139(5) -.049(5) .006(5) -.025(4) C23' .052(2) .051(2) .0451(15) .002(2) .0010(15) -.0033(13) C24' .092(3) .074(2) .069(2) -.018(3) -.008(2) -.024(2) O1' .051(2) .079(2) .0596(13) .0095(14) -.0032(12) -.0033(12) O2' .076(2) .066(2) .0684(15) -.0011(15) .0110(15) .0135(13) O3' .439(12) .110(3) .107(3) -.106(6) .134(5) -.022(3) O4' .123(3) .166(4) .058(2) -.022(3) .023(2) -.029(2) O5' .255(6) .052(2) .142(3) .002(3) -.101(4) .008(2) O6' .106(3) .075(2) .093(2) -.014(2) .010(2) -.008(2) O7' .073(2) .072(2) .0498(12) -.0164(15) .0033(12) -.0151(11) O8' .055(2) .078(2) .0657(15) -.0120(14) .0086(13) -.0075(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 C2 . 1.527(5) no C1 C10 . 1.546(5) no C1 H1A . .970 no C1 H1B . .970 no C2 C3 . 1.529(5) no C2 H2A . .970 no C2 H2B . .970 no C3 C19 . 1.514(6) no C3 C21 . 1.531(5) no C3 C4 . 1.540(5) no C4 C5 . 1.522(4) no C4 H4A . .970 no C4 H4B . .970 no C5 C6 . 1.495(5) no C5 C10 . 1.542(5) no C5 H5 . .980 no C6 C7 . 1.317(5) no C6 H6 . .930 no C7 C8 . 1.492(5) no C7 H7 . .930 no C8 C14 . 1.520(4) no C8 C9 . 1.540(4) no C8 H8 . .980 no C9 C11 . 1.515(5) no C9 C10 . 1.547(4) no C9 H9 . .980 no C10 C18 . 1.530(5) no C11 O1 . 1.228(4) no C11 C12 . 1.513(5) no C12 C13 . 1.527(5) no C12 H12A . .970 no C12 H12B . .970 no C13 C23 . 1.518(5) no C13 C17 . 1.527(5) no C13 C14 . 1.546(5) no C14 C15 . 1.530(5) no C14 H14 . .980 no C15 C16 . 1.524(5) no C15 H15A . .970 no C15 H15B . .970 no C16 C17 . 1.523(6) no C16 H16A . .970 no C16 H16B . .970 no C17 O2 . 1.214(4) no C18 H18A . .960 no C18 H18B . .960 no C18 H18C . .960 no C19 O3 . 1.204(5) no C19 O4 . 1.329(5) no C20 O4 . 1.447(6) no C20 H20A . .960 no C20 H20B . .960 no C20 H20C . .960 no C21 O5 . 1.194(5) no C21 O6 . 1.320(5) no C22 O6 . 1.447(4) no C22 H22A . .960 no C22 H22B . .960 no C22 H22C . .960 no C23 O7 . 1.204(4) no C23 O8 . 1.322(4) no C24 O8 . 1.445(5) no C24 H24A . .960 no C24 H24B . .960 no C24 H24C . .960 no C1' C2' . 1.530(5) no C1' C10' . 1.533(5) no C1' H1'1 . .970 no C1' H1'2 . .970 no C2' C3' . 1.540(6) no C2' H2'1 . .970 no C2' H2'2 . .970 no C3' C19' . 1.517(6) no C3' C21' . 1.531(7) no C3' C4' . 1.531(6) no C4' C5' . 1.517(5) no C4' H4'1 . .970 no C4' H4'2 . .970 no C5' C6' . 1.501(5) no C5' C10' . 1.552(5) no C5' H5' . .980 no C6' C7' . 1.327(5) no C6' H6' . .930 no C7' C8' . 1.495(5) no C7' H7' . .930 no C8' C14' . 1.530(4) no C8' C9' . 1.545(5) no C8' H8' . .980 no C9' C11' . 1.513(5) no C9' C10' . 1.555(4) no C9' H9' . .980 no C10' C18' . 1.526(5) no C11' O1' . 1.227(4) no C11' C12' . 1.513(5) no C12' C13' . 1.528(5) no C12' H12C . .970 no C12' H12D . .970 no C13' C17' . 1.517(5) no C13' C23' . 1.520(5) no C13' C14' . 1.545(4) no C14' C15' . 1.525(5) no C14' H14' . .980 no C15' C16' . 1.524(5) no C15' H15C . .970 no C15' H15D . .970 no C16' C17' . 1.508(5) no C16' H16C . .970 no C16' H16D . .970 no C17' O2' . 1.222(4) no C18' H18D . .960 no C18' H18E . .960 no C18' H18F . .960 no C19' O3' . 1.170(7) no C19' O4' . 1.251(5) no C20' O4' . 1.471(6) no C20' H20D . .960 no C20' H20E . .960 no C20' H20F . .960 no C21' O5' . 1.190(5) no C21' O6' . 1.315(7) no C22' O6' . 1.436(7) no C22' H22D . .960 no C22' H22E . .960 no C22' H22F . .960 no C23' O8' . 1.205(4) no C23' O7' . 1.326(4) no C24' O7' . 1.456(5) no C24' H24D . .960 no C24' H24E . .960 no C24' H24F . .960 no