data_2010303
_journal_name_full  'Acta Crystallographica'
_journal_year  1994
_journal_volume  C50
_journal_page_first  2085
_journal_page_last  2087
_publ_section_title
;
Camphene-1-carboxylic Acid: Stereochemistry of the Namekin Shift
;
loop_
_publ_author_name
  'Cameron, T.S.'
  'Jochem, K.'
  'Morris, D.G.'
  'Maguire, J.'
_chemical_formula_sum  'C11 H16 O2'
_chemical_formula_weight  180
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2y1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,y+1/2,-z'
_cell_length_a  6.193(2)
_cell_length_b  10.609(2)
_cell_length_c  15.492(4)
_cell_angle_alpha  90
_cell_angle_beta  86.42(2)
_cell_angle_gamma  90
_cell_volume  1015.90(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  291
_exptl_crystal_density_diffrn  1.11
_refine_ls_R_factor_obs  0.0407
_refine_ls_wR_factor_obs  0.0429
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
  C1 -.0662(10) -.1892(6) .0522(4) .0387(14)
  C2 -.1097(10) -.2796(6) .1249(4) .0442(15)
  C3 .0076(11) -.2289(7) .2011(4) .0520(17)
  C4 .1093(12) -.1064(8) .1619(4) .0624(19)
  C5 .2971(11) -.1377(8) .0947(5) ?
  C6 .1783(10) -.2033(7) .0214(4) ?
  C7 -.0635(12) -.0625(6) .1000(4) .0497(17)
  C8 -.2220(13) -.3842(8) .1263(5) .066(2)
  C9 -.1558(16) -.1957(11) .2767(5) ?
  C10 .1725(14) -.3219(8) .2342(5) ?
  C11 -.2018(11) -.1963(6) -.0228(4) .0452(16)
  O1 -.2468(10) -.0913(5) -.0591(3) ?
  O2 -.2686(10) -.2964(5) -.0508(3) ?
  H4 .1597(9) -.0442(6) .2121(4) .070(16)
  H51 .3803(9) -.0541(6) .0709(4) .12(3)
  H52 .4136(9) -.2014(6) .1211(4) .12(2)
  H61 .2225(8) -.3014(6) .0163(3) .13(3)
  H62 .2120(8) -.1567(6) -.0393(3) .039(12)
  H71 -.2155(9) -.0391(5) .1342(3) .032(11)
  H72 -.0099(9) .0147(5) .0593(3) .045(13)
  H81 -.309(10) -.412(6) .071(3) .011(2)
  H82 -.277(11) -.445(5) .179(3) .011(2)
  H91 -.2761(13) -.1306(9) .2581(4) .078(19)
  H92 -.2319(13) -.2821(9) .3003(4) .13(3)
  H93 -.0651(13) -.1553(9) .3275(4) .12(3)
  H101 .2953(12) -.3485(7) .1854(5) .09(2)
  H102 .2404(12) -.2609(7) .2811(5) .19(4)
  H103 .1065(12) -.4052(7) .2661(5) .15(3)
  H1 -.298(13) -.107(12) -.117(3) .026(5)
  C1' -.6555(10) -.2302(6) -.3046(4) .0447(16)
  C2' -.6046(11) -.3361(6) -.3690(4) .0454(17)
  C3' -.7052(11) -.2970(7) -.4527(4) .0529(17)
  C4' -.8135(11) -.1717(6) -.4258(4) .0508(18)
  C5' -1.0062(11) -.1940(9) -.3620(5) ?
  C6' -.9052(11) -.2406(8) -.2789(5) ?
  C7' -.6487(11) -.1155(7) -.3640(4) .0515(17)
  C8' -.4879(12) -.4380(7) -.3576(5) .0600(19)
  C9' -.5248(13) -.2782(8) -.5255(5) ?
  C10' -.8593(14) -.3987(9) -.4804(5) ?
  C11' -.5254(11) -.2212(7) -.2271(4) .0459(16)
  O1' -.5154(10) -.3215(5) -.1806(3) ?
  O2' -.4380(9) -.1225(5) -.2079(3) ?
  H4' -.8548(9) -.1183(5) -.4817(3) .071(15)
  H51' -1.1121(9) -.2649(7) -.3869(4) .051(14)
  H52' -1.0967(9) -.1077(7) -.3507(4) .11(2)
  H61' -.9521(8) -.3361(3) -.2633(4) .011(2)
  H62' -.9511(8) -.1799(6) -.2243(4) .0068(16)
  H71' -.4906(9) -.0996(5) -.3958(3) .0050(13)
  H72' -.7055(9) -.0298(5) -.3328(3) .0717(16)
  H81' -.430(12)  -.475(7)  -.298(3)  .12(3)
  H82' -.461(9)  -.506(4)  -.408(2)  .0066(16)
  H91' -.4221(10) -.2032(7) -.5051(4) .091(2)
  H92' -.4296(10) -.3625(7) -.5374(4) .016(3)
  H93' -.5976(10) -.2508(7) -.5843(4) .010(2)
  H1O1' -.9861(11) -.4164(7) -.4306(4) .0061(16)
  H1O2' -.9306(11) -.3651(7) -.5380(4) .009(2)
  H1O3' -.7743(11) -.4863(7) -.4953(4) .021(5)
  H11' -.424(7)  -.305(5)  -.131(2)  .0079(17)
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 . . 1.491(9) yes
  C1 C6 . . 1.566(9) yes
  C1 C7 . . 1.536(9) yes
  C1 C11 . . 1.477(9) yes
  C2 C3 . . 1.522(9) yes
  C2 C8 . . 1.310(10) yes
  C3 C4 . . 1.552(10) yes
  C3 C9 . . 1.540(12) yes
  C3 C10 . . 1.532(11) yes
  C4 C5 . . 1.547(11) yes
  C4 C7 . . 1.552(10) yes
  C5 C6 . . 1.556(10) yes
  C11 O1 . . 1.287(8) yes
  C11 O2 . . 1.229(8) yes
  C1' C2' . . 1.521(9) yes
  C1' C6' . . 1.577(10) yes
  C1' C7' . . 1.524(9) yes
  C1' C11' . . 1.490(9) yes
  C2' C3' . . 1.532(9) yes
  C2' C8' . . 1.318(10) yes
  C3' C4' . . 1.535(10) yes
  C3' C9' . . 1.549(11) yes
  C3' C10' . . 1.521(11) yes
  C4' C5' . . 1.519(10) yes
  C4' C7' . . 1.560(10) yes
  C5' C6' . . 1.547(11) yes
  C11' O1' . . 1.289(9) yes
  C11' O2' . . 1.223(8) yes