#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011487.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_2011487
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1377
_journal_page_last  1379
_publ_section_title
;
A norbornenyl derivative with through-space ketone \p-interaction
;
loop_
_publ_author_name
  'Lloyd, Barry A.'
  'Arif, Atta M.'
  'Allred, Evan L.'
_chemical_formula_sum  'C19 H17 Br O3'
_chemical_formula_weight  373.24
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z'
_cell_length_a  11.3936(3)
_cell_length_b  8.2659(2)
_cell_length_c  16.9840(5)
_cell_angle_alpha  90
_cell_angle_beta  90.6750(17)
_cell_angle_gamma  90
_cell_volume  1599.41(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  148.00(10)
_exptl_crystal_density_diffrn  1.55
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
  Br1  .02746(2)  .11759(3)  .317324(12)  .04828(8) Uani d . 1 . . Br
  O1  .30432(13)  -.05847(19) 1.00623(8)  .0411(3) Uani d . 1 . . O
  O2  .45118(11)  .0937(2)  .60835(8)  .0407(3) Uani d . 1 . . O
  O3  .29321(10)  .17207(16)  .67655(7)  .0281(3) Uani d . 1 . . O
  C1  .29256(15)  .2448(2)  .81580(10)  .0268(3) Uani d . 1 . . C
  H1  .2540(19)  .352(3)  .8111(13)  .037(6) Uiso d . 1 . . H
  C2  .20800(14)  .0979(2)  .82345(10)  .0247(3) Uani d . 1 . . C
  H2  .1442(18)  .109(2)  .7871(12)  .028(5) Uiso d . 1 . . H
  C3  .16542(15)  .0540(2)  .90637(10)  .0295(4) Uani d . 1 . . C
  H3  .1408(19)  .143(3)  .9396(13)  .037(6) Uiso d . 1 . . H
  C4  .07566(18)  -.0844(3)  .89535(12)  .0392(5) Uani d . 1 . . C
  H4A  .037(2)  -.111(3)  .9421(14)  .040(6) Uiso d . 1 . . H
  H4B  .0167(19)  -.056(3)  .8555(14)  .038(6) Uiso d . 1 . . H
  C5  .1525(2)  -.2319(3)  .87059(13)  .0432(5) Uani d . 1 . . C
  H5A  .148(2)  -.318(3)  .9078(15)  .055(7) Uiso d . 1 . . H
  H5B  .132(2)  -.277(3)  .8192(14)  .046(6) Uiso d . 1 . . H
  C6  .27929(18)  -.1646(2)  .87042(11)  .0337(4) Uani d . 1 . . C
  H6  .338(2)  -.238(3)  .8757(13)  .041(6) Uiso d . 1 . . H
  C7  .28821(15)  -.0495(2)  .80002(10)  .0262(3) Uani d . 1 . . C
  H7  .2616(16)  -.100(2)  .7532(11)  .021(5) Uiso d . 1 . . H
  C8  .40863(15)  .0327(2)  .78465(10)  .0277(3) Uani d . 1 . . C
  H8  .4600(18)  -.034(3)  .7551(12)  .032(5) Uiso d . 1 . . H
  C9  .45407(16)  .1045(2)  .86126(11)  .0312(4) Uani d . 1 . . C
  H9  .515(2)  .062(3)  .8934(14)  .042(6) Uiso d . 1 . . H
  C10  .38586(16)  .2291(2)  .87942(11)  .0298(4) Uani d . 1 . . C
  H10  .3879(18)  .295(3)  .9260(13)  .034(5) Uiso d . 1 . . H
  C11  .36713(15)  .1911(2)  .74588(10)  .0271(3) Uani d . 1 . . C
  H11  .4299(19)  .265(3)  .7347(12)  .035(6) Uiso d . 1 . . H
  C12  .26467(16)  -.0498(2)  .93999(10)  .0312(4) Uani d . 1 . . C
  C13  .34773(16)  .1254(2)  .61032(10)  .0286(3) Uani d . 1 . . C
  C14  .26720(15)  .1199(2)  .54091(10)  .0274(3) Uani d . 1 . . C
  C15  .15020(17)  .1651(3)  .54608(11)  .0337(4) Uani d . 1 . . C
  H15  .121(2)  .198(3)  .5945(14)  .042(6) Uiso d . 1 . . H
  C16  .07909(19)  .1641(3)  .47929(12)  .0378(4) Uani d . 1 . . C
  H16  .001(2)  .192(3)  .4831(15)  .053(7) Uiso d . 1 . . H
  C17  .12596(18)  .1177(2)  .40830(11)  .0337(4) Uani d . 1 . . C
  C18  .2419(2)  .0714(3)  .40175(12)  .0385(4) Uani d . 1 . . C
  H18  .272(2)  .036(3)  .3561(15)  .055(7) Uiso d . 1 . . H
  C19  .31248(18)  .0719(3)  .46895(11)  .0354(4) Uani d . 1 . . C
  H19  .392(2)  .040(3)  .4651(14)  .046(6) Uiso d . 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
  Br1  .07021(17)  .04111(12)  .03298(11)  -.00157(11)  -.02163(10)  .00000(9)
  O1  .0454(8)  .0470(8)  .0304(7)  -.0117(7)  -.0158(6)  .0095(6)
  O2  .0255(6)  .0644(10)  .0322(7)  .0014(7)  .0023(5)  -.0046(7)
  O3  .0253(6)  .0376(7)  .0214(5)  .0021(5)  -.0005(4)  .0006(5)
  C1  .0290(8)  .0256(8)  .0258(8)  .0016(7)  -.0007(6)  -.0015(6)
  C2  .0206(7)  .0317(9)  .0218(7)  .0007(6)  -.0035(6)  .0012(6)
  C3  .0263(8)  .0385(10)  .0236(8)  -.0020(8)  -.0037(6)  .0020(7)
  C4  .0311(9)  .0573(13)  .0291(9)  -.0142(9)  -.0055(8)  .0100(9)
  C5  .0528(13)  .0381(11)  .0384(11)  -.0203(10)  -.0179(10)  .0109(9)
  C6  .0378(10)  .0283(8)  .0346(9)  .0002(8)  -.0146(8)  .0045(7)
  C7  .0275(8)  .0245(8)  .0264(8)  -.0004(7)  -.0076(6)  -.0010(6)
  C8  .0234(8)  .0327(9)  .0270(8)  .0049(7)  -.0036(6)  -.0041(7)
  C9  .0256(8)  .0392(10)  .0287(8)  -.0035(8)  -.0068(7)  .0000(7)
  C10  .0314(9)  .0320(9)  .0259(8)  -.0069(7)  -.0026(7)  -.0037(7)
  C11  .0234(8)  .0330(9)  .0249(8)  -.0029(7)  -.0010(6)  -.0007(7)
  C12  .0324(9)  .0339(9)  .0271(8)  -.0099(8)  -.0080(7)  .0069(7)
  C13  .0273(8)  .0332(9)  .0255(8)  -.0027(7)  .0032(6)  .0002(7)
  C14  .0288(8)  .0292(8)  .0241(7)  -.0024(7)  .0002(6)  -.0002(6)
  C15  .0326(9)  .0415(10)  .0269(8)  .0042(8)  -.0016(7)  -.0033(8)
  C16  .0363(10)  .0439(11)  .0332(9)  .0062(9)  -.0066(8)  -.0036(8)
  C17  .0467(11)  .0276(8)  .0264(8)  -.0036(8)  -.0094(7)  .0001(7)
  C18  .0480(12)  .0425(10)  .0250(8)  -.0041(9)  .0038(8)  -.0064(8)
  C19  .0338(10)  .0417(10)  .0307(9)  -.0007(9)  .0039(7)  -.0059(8)
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
  Br1 C17 . 1.8989(18) ?
  O1 C12 . 1.210(2) y
  O2 C13 . 1.208(2) ?
  O3 C13 . 1.348(2) ?
  O3 C11 . 1.448(2) y
  C1 C10 . 1.512(2) y
  C1 C11 . 1.534(2) y
  C1 C2 . 1.557(2) y
  C1 H1 .  .99(2) ?
  C2 C3 . 1.538(2) y
  C2 C7 . 1.577(2) y
  C2 H2 .  .95(2) ?
  C3 C12 . 1.525(3) y
  C3 C4 . 1.545(3) y
  C3 H3 .  .97(2) ?
  C4 C5 . 1.561(3) y
  C4 H4A .  .94(2) ?
  C4 H4B .  .98(2) ?
  C5 C6 . 1.548(3) y
  C5 H5A .  .95(3) ?
  C5 H5B .  .97(2) ?
  C6 C12 . 1.526(3) y
  C6 C7 . 1.532(3) y
  C6 H6 .  .91(2) ?
  C7 C8 . 1.556(2) y
  C7 H7 .  .944(19) ?
  C8 C9 . 1.516(2) y
  C8 C11 . 1.537(3) y
  C8 H8 .  .95(2) ?
  C9 C10 . 1.328(3) y
  C9 H9 .  .94(2) ?
  C10 H10 .  .96(2) ?
  C11 H11 .  .96(2) ?
  C13 C14 . 1.486(2) ?
  C14 C15 . 1.388(3) ?
  C14 C19 . 1.390(3) ?
  C15 C16 . 1.386(3) ?
  C15 H15 .  .93(2) ?
  C16 C17 . 1.379(3) ?
  C16 H16 .  .93(3) ?
  C17 C18 . 1.381(3) ?
  C18 C19 . 1.388(3) ?
  C18 H18 .  .90(3) ?
  C19 H19 .  .95(2) ?