#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012229.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_2012229
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1118
_journal_page_last  1119
_publ_section_title
;
1,4-Methano-11a-methyl-2,3,4,4a,11,11a-hexahydro-1H-benzo[b]fluoren-11-one
;
loop_
_publ_author_name
  'Anwar Usman'
  'Ibrahim Abdul Razak'
  'Suchada Chantrapromma'
  'Sujit K. Ghorai'
  'Dipakranjan Mal'
  'Hoong-Kun Fun'
  'Gur Dayal Nigam'
_chemical_formula_moiety  'C19 H16 O'
_chemical_formula_sum  'C19 H16 O'
_chemical_formula_iupac  'C19 H16 O'
_chemical_formula_weight  260.32
_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  6.23030(10)
_cell_length_b  20.5610(3)
_cell_length_c  10.7476(2)
_cell_angle_alpha  90.00
_cell_angle_beta  96.6650(10)
_cell_angle_gamma  90.00
_cell_volume  1367.48(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.264
_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_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
  O1A  .1597(3)  .31928(12)  .7501(2)  .0537(6) Uani d . 1 . . O
  C1A  .3049(4)  .30452(15)  .6895(3)  .0380(6) Uani d . 1 . . C
  C2A  .2976(4)  .30788(13)  .5523(2)  .0344(5) Uani d . 1 . . C
  C3A  .1345(4)  .33000(13)  .4673(3)  .0366(6) Uani d . 1 . . C
  H3A  .0099  .3474  .4940  .044 Uiso calc R 1 . . H
  C4A  .1568(4)  .32612(13)  .3391(3)  .0352(6) Uani d . 1 . . C
  C5A  -.0077(5)  .34731(15)  .2463(3)  .0436(7) Uani d . 1 . . C
  H5A  -.1346  .3646  .2703  .052 Uiso calc R 1 . . H
  C6A  .0159(6)  .34294(17)  .1236(3)  .0525(8) Uani d . 1 . . C
  H6A  -.0942  .3571  .0639  .063 Uiso calc R 1 . . H
  C7A  .2068(5)  .31694(17)  .0856(3)  .0526(8) Uani d . 1 . . C
  H7A  .2215  .3136  .0007  .063 Uiso calc R 1 . . H
  C8A  .3689(5)  .29689(15)  .1712(3)  .0446(7) Uani d . 1 . . C
  H8A  .4947  .2804  .1444  .054 Uiso calc R 1 . . H
  C9A  .3508(5)  .30040(13)  .3009(2)  .0356(6) Uani d . 1 . . C
  C10A  .5185(4)  .27938(14)  .3919(2)  .0366(6) Uani d . 1 . . C
  H10A  .6465  .2633  .3672  .044 Uiso calc R 1 . . H
  C11A  .4925(4)  .28272(13)  .5151(3)  .0346(6) Uani d . 1 . . C
  C12A  .6425(4)  .26236(15)  .6274(2)  .0400(6) Uani d . 1 . . C
  H12A  .7798  .2859  .6308  .048 Uiso calc R 1 . . H
  C13A  .6830(5)  .18773(17)  .6428(3)  .0534(8) Uani d . 1 . . C
  H13A  .7928  .1694  .5945  .064 Uiso calc R 1 . . H
  C14A  .7330(7)  .1837(2)  .7857(3)  .0716(12) Uani d . 1 . . C
  H14A  .7547  .1395  .8161  .086 Uiso calc R 1 . . H
  H14B  .8533  .2111  .8185  .086 Uiso calc R 1 . . H
  C15A  .5129(6)  .21177(19)  .8085(3)  .0590(9) Uani d . 1 . . C
  H15A  .4836  .2130  .8961  .071 Uiso calc R 1 . . H
  C16A  .5242(4)  .27925(16)  .7432(2)  .0401(6) Uani d . 1 . . C
  C17A  .3652(7)  .16960(17)  .7233(4)  .0662(10) Uani d . 1 . . C
  H17A  .2276  .1559  .7371  .079 Uiso calc R 1 . . H
  C18A  .4653(7)  .15527(17)  .6247(4)  .0640(9) Uani d . 1 . . C
  H18A  .4110  .1298  .5568  .077 Uiso calc R 1 . . H
  C19A  .6370(5)  .3311(2)  .8270(3)  .0639(10) Uani d . 1 . . C
  H19A  .6424  .3709  .7807  .096 Uiso calc R 1 . . H
  H19B  .7814  .3172  .8557  .096 Uiso calc R 1 . . H
  H19C  .5588  .3381  .8977  .096 Uiso calc R 1 . . H
  O1B  -.3056(3)  .49627(12)  .81658(18)  .0492(5) Uani d . 1 . . O
  C1B  -.1580(4)  .50867(13)  .7544(2)  .0331(5) Uani d . 1 . . C
  C2B  -.1657(4)  .50406(13)  .6185(2)  .0312(5) Uani d . 1 . . C
  C3B  -.3304(4)  .48180(13)  .5332(2)  .0343(6) Uani d . 1 . . C
  H3B  -.4552  .4646  .5601  .041 Uiso calc R 1 . . H
  C4B  -.3087(4)  .48520(12)  .4056(2)  .0342(6) Uani d . 1 . . C
  C5B  -.4767(5)  .46507(14)  .3132(3)  .0437(7) Uani d . 1 . . C
  H5B  -.6031  .4477  .3376  .052 Uiso calc R 1 . . H
  C6B  -.4551(6)  .47084(17)  .1901(3)  .0523(8) Uani d . 1 . . C
  H6B  -.5669  .4574  .1308  .063 Uiso calc R 1 . . H
  C7B  -.2675(5)  .49672(17)  .1508(3)  .0510(8) Uani d . 1 . . C
  H7B  -.2559  .5010  .0657  .061 Uiso calc R 1 . . H
  C8B  -.1009(5)  .51575(15)  .2365(3)  .0427(7) Uani d . 1 . . C
  H8B  .0239  .5325  .2090  .051 Uiso calc R 1 . . H
  C9B  -.1143(4)  .51054(13)  .3659(2)  .0335(5) Uani d . 1 . . C
  C10B  .0538(4)  .53103(13)  .4571(2)  .0351(6) Uani d . 1 . . C
  H10B  .1819  .5469  .4323  .042 Uiso calc R 1 . . H
  C11B  .0294(4)  .52768(13)  .5812(2)  .0316(5) Uani d . 1 . . C
  C12B  .1824(4)  .54774(14)  .6926(2)  .0359(6) Uani d . 1 . . C
  H12B  .3179  .5233  .6956  .043 Uiso calc R 1 . . H
  C13B  .2289(5)  .62194(18)  .7071(3)  .0505(8) Uani d . 1 . . C
  H13B  .3388  .6393  .6579  .061 Uiso calc R 1 . . H
  C14B  .2825(6)  .6255(2)  .8496(3)  .0626(10) Uani d . 1 . . C
  H14C  .3075  .6696  .8801  .075 Uiso calc R 1 . . H
  H14D  .4020  .5976  .8811  .075 Uiso calc R 1 . . H
  C15B  .0626(5)  .59857(16)  .8749(3)  .0524(8) Uani d . 1 . . C
  H15B  .0361  .5973  .9630  .063 Uiso calc R 1 . . H
  C16B  .0646(4)  .53147(14)  .8076(2)  .0356(6) Uani d . 1 . . C
  C17B  -.0852(6)  .64297(16)  .7901(4)  .0615(9) Uani d . 1 . . C
  H17B  -.2205  .6580  .8054  .074 Uiso calc R 1 . . H
  C18B  .0132(6)  .65629(16)  .6913(4)  .0600(9) Uani d . 1 . . C
  H18B  -.0403  .6822  .6239  .072 Uiso calc R 1 . . H
  C19B  .1712(5)  .47810(18)  .8907(3)  .0551(8) Uani d . 1 . . C
  H19D  .1751  .4387  .8431  .083 Uiso calc R 1 . . H
  H19E  .0900  .4710  .9601  .083 Uiso calc R 1 . . H
  H19F  .3159  .4909  .9214  .083 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
  O1A  .0393(11)  .0858(16)  .0380(10)  .0106(10)  .0137(9)  -.0075(10)
  C1A  .0330(14)  .0486(15)  .0333(13)  .0008(12)  .0078(11)  -.0060(12)
  C2A  .0316(12)  .0405(14)  .0318(12)  .0026(11)  .0067(10)  -.0024(11)
  C3A  .0321(14)  .0407(15)  .0377(14)  .0055(12)  .0075(11)  -.0007(12)
  C4A  .0355(14)  .0354(13)  .0348(13)  -.0014(11)  .0045(11)  .0016(11)
  C5A  .0417(16)  .0484(16)  .0398(15)  .0039(13)  .0011(12)  .0045(13)
  C6A  .0548(19)  .0607(19)  .0400(15)  .0004(15)  -.0034(14)  .0042(15)
  C7A  .064(2)  .0616(19)  .0317(13)  -.0005(16)  .0051(13)  .0020(14)
  C8A  .0533(18)  .0473(16)  .0358(13)  .0009(14)  .0153(13)  .0014(13)
  C9A  .0383(14)  .0373(14)  .0323(13)  -.0010(11)  .0080(11)  .0004(11)
  C10A  .0322(13)  .0430(14)  .0365(13)  .0031(11)  .0119(11)  -.0009(12)
  C11A  .0286(13)  .0399(14)  .0353(13)  .0011(11)  .0041(11)  .0002(11)
  C12A  .0323(14)  .0540(18)  .0338(13)  .0028(12)  .0035(11)  -.0012(12)
  C13A  .0520(18)  .060(2)  .0486(18)  .0229(15)  .0063(14)  .0051(15)
  C14A  .073(2)  .089(3)  .053(2)  .037(2)  .0053(19)  .018(2)
  C15A  .0606(19)  .074(2)  .0449(16)  .0205(18)  .0145(15)  .0202(17)
  C16A  .0337(13)  .0552(17)  .0312(12)  .0016(12)  .0032(10)  -.0010(12)
  C17A  .070(2)  .0482(19)  .081(3)  -.0023(17)  .013(2)  .0168(18)
  C18A  .078(2)  .0414(17)  .072(2)  .0063(17)  .005(2)  .0015(16)
  C19A  .0459(18)  .092(3)  .0523(18)  -.0057(18)  .0002(15)  -.0252(19)
  O1B  .0371(10)  .0756(15)  .0368(10)  -.0096(10)  .0125(8)  .0021(10)
  C1B  .0308(12)  .0395(13)  .0301(11)  -.0001(10)  .0082(9)  .0018(11)
  C2B  .0265(12)  .0377(13)  .0302(11)  -.0019(11)  .0062(9)  .0002(11)
  C3B  .0279(12)  .0405(14)  .0351(13)  -.0031(11)  .0063(10)  -.0022(11)
  C4B  .0328(14)  .0360(14)  .0331(12)  .0004(11)  .0014(10)  -.0035(11)
  C5B  .0391(15)  .0478(16)  .0423(15)  .0009(12)  -.0027(12)  -.0073(13)
  C6B  .0544(19)  .0584(19)  .0406(16)  .0030(15)  -.0095(14)  -.0090(15)
  C7B  .063(2)  .0587(18)  .0302(13)  .0119(16)  -.0010(13)  -.0005(14)
  C8B  .0501(17)  .0482(17)  .0304(12)  .0032(14)  .0082(12)  .0010(12)
  C9B  .0376(13)  .0345(13)  .0285(11)  .0053(11)  .0051(10)  -.0007(11)
  C10B  .0314(13)  .0424(14)  .0320(12)  -.0015(12)  .0064(10)  -.0003(11)
  C11B  .0273(12)  .0383(13)  .0297(12)  .0005(11)  .0053(10)  .0007(11)
  C12B  .0237(11)  .0497(16)  .0339(12)  -.0028(10)  .0013(10)  -.0019(11)
  C13B  .0518(18)  .0586(19)  .0412(16)  -.0235(16)  .0062(14)  -.0045(14)
  C14B  .061(2)  .077(2)  .0484(19)  -.0311(19)  .0040(16)  -.0160(17)
  C15B  .0531(18)  .065(2)  .0404(15)  -.0138(15)  .0098(13)  -.0152(15)
  C16B  .0293(12)  .0488(15)  .0285(11)  -.0027(11)  .0029(10)  .0002(11)
  C17B  .064(2)  .0460(18)  .075(2)  .0024(15)  .0128(19)  -.0153(17)
  C18B  .069(2)  .0394(17)  .070(2)  -.0055(15)  .0042(18)  -.0010(15)
  C19B  .0441(16)  .076(2)  .0445(15)  .0076(16)  .0015(13)  .0196(16)
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
  O1A C1A . 1.214(3) yes
  C1A C2A . 1.472(4) ?
  C1A C16A . 1.512(4) yes
  C2A C3A . 1.363(4) yes
  C2A C11A . 1.419(4) ?
  C3A C4A . 1.403(4) ?
  C3A H3A .  .9300 ?
  C4A C5A . 1.414(4) ?
  C4A C9A . 1.423(4) ?
  C5A C6A . 1.346(4) ?
  C5A H5A .  .9300 ?
  C6A C7A . 1.408(5) ?
  C6A H6A .  .9300 ?
  C7A C8A . 1.349(4) ?
  C7A H7A .  .9300 ?
  C8A C9A . 1.414(4) ?
  C8A H8A .  .9300 ?
  C9A C10A . 1.413(4) ?
  C10A C11A . 1.355(4) ?
  C10A H10A .  .9300 ?
  C11A C12A . 1.498(4) ?
  C12A C16A . 1.557(4) ?
  C12A C13A . 1.561(5) ?
  C12A H12A .  .9800 ?
  C13A C18A . 1.504(5) ?
  C13A C14A . 1.534(5) ?
  C13A H13A .  .9800 ?
  C14A C15A . 1.533(5) yes
  C14A H14A .  .9700 ?
  C14A H14B .  .9700 ?
  C15A C17A . 1.497(6) yes
  C15A C16A . 1.560(5) ?
  C15A H15A .  .9800 ?
  C16A C19A . 1.515(4) yes
  C17A C18A . 1.323(5) ?
  C17A H17A .  .9300 ?
  C18A H18A .  .9300 ?
  C19A H19A .  .9600 ?
  C19A H19B .  .9600 ?
  C19A H19C .  .9600 ?
  O1B C1B . 1.225(3) yes
  C1B C2B . 1.459(3) ?
  C1B C16B . 1.512(3) yes
  C2B C3B . 1.374(3) yes
  C2B C11B . 1.409(3) ?
  C3B C4B . 1.395(4) ?
  C3B H3B .  .9300 ?
  C4B C5B . 1.418(4) ?
  C4B C9B . 1.428(4) ?
  C5B C6B . 1.350(5) ?
  C5B H5B .  .9300 ?
  C6B C7B . 1.394(5) ?
  C6B H6B .  .9300 ?
  C7B C8B . 1.363(4) ?
  C7B H7B .  .9300 ?
  C8B C9B . 1.407(3) ?
  C8B H8B .  .9300 ?
  C9B C10B . 1.413(4) ?
  C10B C11B . 1.361(3) ?
  C10B H10B .  .9300 ?
  C11B C12B . 1.499(3) ?
  C12B C16B . 1.546(3) yes
  C12B C13B . 1.557(5) ?
  C12B H12B .  .9800 ?
  C13B C18B . 1.510(5) ?
  C13B C14B . 1.531(4) ?
  C13B H13B .  .9800 ?
  C14B C15B . 1.531(5) yes
  C14B H14C .  .9700 ?
  C14B H14D .  .9700 ?
  C15B C17B . 1.522(5) yes
  C15B C16B . 1.558(4) ?
  C15B H15B .  .9800 ?
  C16B C19B . 1.518(4) yes
  C17B C18B . 1.315(5) ?
  C17B H17B .  .9300 ?
  C18B H18B .  .9300 ?
  C19B H19D .  .9600 ?
  C19B H19E .  .9600 ?
  C19B H19F .  .9600 ?