data_2006575
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  1490
_journal_page_last  1493
_publ_section_title
;
Unique trans-syn-cis [6.6.7] Tricycle
Derivative from Transannular Diels-Alder Contraction of
a Model 15-Membered trans-cis-cis Macrocyclic Triene
;
loop_
_publ_author_name
  ' Drouin, Marc'
  'Hall, Dennis G.'
  "Caill\'e, Alain-S\'ebastien"
  'Pierre Deslongchamps'
_chemical_formula_moiety  'C24 H32 O9 '
_chemical_formula_sum  'C24 H32 O9 '
_chemical_formula_weight  464.51
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  x,y,z
  -x,-y,-z
_cell_length_a  6.9449(5)
_cell_length_b  10.5817(5)
_cell_length_c  17.8569(8)
_cell_angle_alpha  74.196(4)
_cell_angle_beta  78.952(4)
_cell_angle_gamma  73.558(4)
_cell_volume  1201.68(12)
_cell_formula_units_Z  2
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.284
_diffrn_ambient_temperature  293
_refine_ls_R_factor_obs  .046
_refine_ls_wR_factor_obs  .061
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
  O1 .9125(3) .0382(2) .11936(13) .0609(8) Uani
  O2 1.1460(3) .1040(2) .15732(14) .0660(9) Uani
  O3 1.5257(3) -.1976(2) .19846(12) .0604(8) Uani
  O4 1.4227(3) -.1389(2) .08009(11) .0530(7) Uani
  O5 .3459(3) -.6428(2) .31138(16) .0740(9) Uani
  O6 .5866(3) -.8230(2) .29158(14) .0591(8) Uani
  O7 .9204(3) -.8506(3) .42205(16) .0856(10) Uani
  O8 .5973(3) -.8206(2) .46907(12) .0574(7) Uani
  O9 1.4614(4) -.4531(3) .07866(17) .0992(14) Uani
  C1 1.1658(4) -.1350(3) .18807(14) .0374(8) Uani
  C2 1.0733(4) -.2294(3) .16093(15) .0401(8) Uani
  C3 1.1520(4) -.3793(3) .19856(15) .0433(9) Uani
  C4 1.1400(4) -.4703(3) .14900(15) .0440(9) Uani
  C5 .9933(5) -.5333(3) .15684(16) .0467(9) Uani
  C6 .8139(4) -.5322(3) .21703(16) .0458(9) Uani
  C7 .8583(4) -.6534(3) .28672(16) .0403(8) Uani
  C8 .6753(4) -.6736(2) .34892(15) .0372(8) Uani
  C9 .5689(4) -.5453(3) .38083(16) .0440(9) Uani
  C10 .6976(5) -.4972(3) .41996(16) .0470(9) Uani
  C11 .7379(4) -.3773(3) .39489(17) .0477(10) Uani
  C12 .8467(5) -.3206(3) .43411(16) .0492(10) Uani
  C13 .9198(5) -.2124(3) .40298(17) .0504(10) Uani
  C14 .9242(4) -.1358(3) .31901(17) .0474(9) Uani
  C15 1.1426(4) -.1600(3) .27812(15) .0426(9) Uani
  C16 1.0770(4) .0148(3) .15384(15) .0416(9) Uani
  C17 .8227(6) .1787(3) .0855(2) .0731(11) Uani
  C18 1.3925(4) -.1609(3) .15814(16) .0416(8) Uani
  C19 1.6309(5) -.1707(4) .04553(19) .0658(11) Uani
  C20 .5159(4) -.7089(3) .31546(16) .0418(9) Uani
  C21 .4408(5) -.8653(3) .2616(2) .0694(14) Uani
  C22 .7494(4) -.7919(3) .41624(16) .0436(9) Uani
  C23 .6473(5) -.9271(3) .53821(19) .0668(11) Uani
  C24 1.3115(6) -.4956(4) .0885(2) .0673(12) Uani
  H2a .92743 -.20154 .17302 .0516 Uiso
  H2b 1.1053 -.21771 .10454 .0516 Uiso
  H3a 1.28807 -.39696 .20422 .0544 Uiso
  H3b 1.08644 -.40385 .24887 .0544 Uiso
  H5 1.00819 -.58450 .12029 .0581 Uiso
  H6a .70181 -.53668 .19357 .0563 Uiso
  H6b .77882 -.44933 .23542 .0563 Uiso
  H7a .96356 -.64101 .31073 .051 Uiso
  H7b .9106 -.73446 .26644 .051 Uiso
  H9a .51585 -.47285 .33785 .0543 Uiso
  H9b .45535 -.56541 .41895 .0543 Uiso
  H10 .74331 -.55514 .46589 .0573 Uiso
  H11 .68660 -.32047 .34968 .0586 Uiso
  H12 .86314 -.36671 .48573 .0604 Uiso
  H13 .97335 -.17704 .43434 .0634 Uiso
  H14a .87789 -.03968 .31736 .0584 Uiso
  H14b .84216 -.16584 .29236 .0584 Uiso
  H15a 1.21148 -.2529 .29949 .0544 Uiso
  H15b 1.20962 -.10072 .29066 .0544 Uiso
  H17a .71078 .17676 .06184 .0812 Uiso
  H17b .91980 .21747 .04697 .0812 Uiso
  H17c .78427 .22548 .12721 .0812 Uiso
  H19a 1.62875 -.15275 -.01002 .0734 Uiso
  H19b 1.69398 -.26358 .06715 .0734 Uiso
  H19c 1.69752 -.11197 .05766 .0734 Uiso
  H21a .51044 -.95015 .24833 .0859 Uiso
  H21b .40073 -.79742 .21553 .0859 Uiso
  H21c .33293 -.87704 .30333 .0859 Uiso
  H23a .52547 -.94445 .57019 .0745 Uiso
  H23b .72671 -.90013 .56678 .0745 Uiso
  H23c .723 -1.00811 .52169 .0745 Uiso
  H24 1.29480 -.54500 .05537 .0811 Uiso
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
  O1 .0569(14) .0468(12) .0838(16) -.0092(10) -.0363(12) -.0077(11)
  O2 .0668(15) .0465(12) .0960(18) -.0214(11) -.0278(13) -.0149(11)
  O3 .0342(12) .0869(16) .0586(13) -.0145(11) -.0127(10) -.0099(11)
  O4 .0364(11) .0740(14) .0472(11) -.0198(10) -.0005(9) -.0082(10)
  O5 .0399(13) .0631(14) .127(2) -.0044(11) -.0349(14) -.0265(14)
  O6 .0435(12) .0543(12) .0944(16) -.0080(10) -.0264(11) -.0334(12)
  O7 .0369(13) .0941(18) .0915(18) -.0039(12) -.0127(12) .0252(14)
  O8 .0431(12) .0612(13) .0558(12) -.0151(10) -.0047(10) .0076(10)
  O9 .0749(19) .155(3) .094(2) -.069(2) .0338(15) -.060(2)
  C1 .0336(14) .0419(14) .0411(14) -.0144(11) -.0076(11) -.0093(11)
  C2 .0360(15) .0451(15) .0439(14) -.0149(12) -.0070(11) -.0113(11)
  C3 .0459(17) .0435(15) .0439(15) -.0169(12) -.0051(12) -.0097(12)
  C4 .0467(16) .0426(15) .0442(15) -.0150(12) .0013(12) -.0130(12)
  C5 .0514(18) .0470(16) .0459(15) -.0163(13) -.0019(13) -.0161(12)
  C6 .0396(16) .0465(15) .0528(16) -.0150(12) -.0043(13) -.0101(13)
  C7 .0289(14) .0435(14) .0508(15) -.0106(11) -.0044(11) -.0132(12)
  C8 .0313(14) .0374(14) .0442(14) -.0119(11) -.0050(11) -.0078(11)
  C9 .0369(15) .0430(15) .0529(16) -.0122(12) -.0005(12) -.0133(12)
  C10 .0483(17) .0474(16) .0461(15) -.0136(13) -.0011(13) -.0134(13)
  C11 .0445(17) .0513(17) .0500(16) -.0154(13) -.0009(13) -.0159(13)
  C12 .0496(18) .0589(18) .0427(15) -.0215(14) .0015(13) -.0140(13)
  C13 .0501(18) .0618(18) .0482(16) -.0234(14) .0016(13) -.0224(14)
  C14 .0475(17) .0451(15) .0525(16) -.0131(13) -.0035(13) -.0161(13)
  C15 .0430(16) .0477(15) .0424(14) -.0176(12) -.0075(12) -.0107(12)
  C16 .0391(15) .0476(16) .0419(14) -.0144(12) -.0050(12) -.0126(12)
  C17 .074(2) .0536(19) .086(2) -.0044(17) -.036(2) -.0006(17)
  C18 .0389(15) .0412(14) .0474(15) -.0162(12) -.0065(12) -.0071(12)
  C19 .0452(19) .085(2) .0599(19) -.0185(17) .0083(15) -.0123(17)
  C20 .0338(15) .0396(14) .0519(16) -.0134(12) -.0091(12) -.0031(12)
  C21 .064(2) .069(2) .095(3) -.0243(17) -.031(2) -.0285(19)
  C22 .0359(16) .0458(15) .0512(16) -.0129(12) -.0081(13) -.0099(12)
  C23 .065(2) .071(2) .0580(19) -.0236(18) -.0169(17) .0090(16)
  C24 .066(2) .085(2) .063(2) -.0353(19) .0136(17) -.0343(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 C2 . . 1.546(3) no
  C1 C15 . . 1.541(4) no
  C1 C16 . . 1.527(4) no
  C1 C18 . . 1.534(4) no
  C2 C3 . . 1.528(4) no
  C2 H2a . . .970 no
  C2 H2b . . .970 no
  C3 C4 . . 1.502(4) no
  C3 H3a . . .930 no
  C3 H3b . . .930 no
  C4 C5 . . 1.334(4) no
  C4 C24 . . 1.464(4) no
  C5 C6 . . 1.481(4) no
  C5 H5 . . .930 no
  C6 C7 . . 1.531(4) no
  C6 H6a . . .970 no
  C6 H6b . . .970 no
  C7 C8 . . 1.542(4) no
  C7 H7a . . .970 no
  C7 H7b . . .970 no
  C8 C9 . . 1.550(3) no
  C8 C20 . . 1.526(4) no
  C8 C22 . . 1.527(4) no
  C9 C10 . . 1.495(4) no
  C9 H9a . . .970 no
  C9 H9b . . .970 no
  C10 C11 . . 1.317(4) no
  C10 H10 . . .930 no
  C11 C12 . . 1.452(4) no
  C11 H11 . . .930 no
  C12 C13 . . 1.323(4) no
  C12 H12 . . .930 no
  C13 C14 . . 1.497(4) no
  C13 H13 . . .930 no
  C14 C15 . . 1.535(4) no
  C14 H14a . . .970 no
  C14 H14b . . .970 no
  C15 H15a . . .970 no
  C15 H15b . . .970 no
  C16 O1 . . 1.331(3) no
  C16 O2 . . 1.193(3) no
  C17 O1 . . 1.448(4) no
  C17 H17a . . .960 no
  C17 H17b . . .960 no
  C17 H17c . . .960 no
  C18 O3 . . 1.194(3) no
  C18 O4 . . 1.334(3) no
  C19 O4 . . 1.442(4) no
  C19 H19a . . .960 no
  C19 H19b . . .960 no
  C19 H19c . . .960 no
  C20 O5 . . 1.194(3) no
  C20 O6 . . 1.322(3) no
  C21 O6 . . 1.452(4) no
  C21 H21a . . .960 no
  C21 H21b . . .960 no
  C21 H21c . . .960 no
  C22 O7 . . 1.183(4) no
  C22 O8 . . 1.320(3) no
  C23 O8 . . 1.449(4) no
  C23 H23a . . .960 no
  C23 H23b . . .960 no
  C23 H23c . . .960 no
  C24 O9 . . 1.212(4) no
  C24 H24 . . .930 no