#------------------------------------------------------------------------------
#$Date: 2008-11-20 21:58:43 +0200 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008117.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_2008117
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  112
_journal_page_last  114
_publ_section_title
;
 Scalarolide and scalarin, sesterterpenes from Cacospongia and
 Ircinia sponges
;
loop_
_publ_author_name
  'Cambie, Richard C.'
  'Rickard, Clifton E. F.'
  'Rutledge, P. Stewart'
  'Yang, Xiao-Shuang'
_chemical_name_common  Scalarolide
_chemical_formula_moiety  'C25 H38 O3'
_chemical_formula_sum  'C25 H38 O3'
_chemical_formula_weight  386.55
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'C 2'
_symmetry_space_group_name_Hall  'C 2y'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z'
_cell_length_a  13.7343(2)
_cell_length_b  6.1274(2)
_cell_length_c  25.2459(7)
_cell_angle_alpha  90.00
_cell_angle_beta  92.2770(10)
_cell_angle_gamma  90.00
_cell_volume  2122.91(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  203(2)
_exptl_crystal_density_diffrn  1.209
_diffrn_ambient_temperature  203(2)
_refine_ls_R_factor_obs  0.0850
_refine_ls_wR_factor_obs  0.2260
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
  O1 0.0822(3) 0.1709(8) 0.83351(17) 0.0721(13) Uani d . 1 . . O
  H1A 0.0791 0.2180 0.8642 0.108 Uiso calc R 1 . . H
  O2 0.1082(4) 0.3546(11) 0.93144(17) 0.0954(19) Uani d . 1 . . O
  C1 0.1860(4) 0.2835(11) 0.6438(2) 0.0587(15) Uani d . 1 . . C
  H1B 0.1230 0.2230 0.6534 0.070 Uiso calc R 1 . . H
  H1C 0.1904 0.4320 0.6581 0.070 Uiso calc R 1 . . H
  C2 0.1889(5) 0.2949(15) 0.5843(2) 0.077(2) Uani d . 1 . . C
  H2A 0.1347 0.3849 0.5705 0.093 Uiso calc R 1 . . H
  H2B 0.1809 0.1479 0.5695 0.093 Uiso calc R 1 . . H
  C3 0.2859(5) 0.3926(16) 0.5667(2) 0.083(2) Uani d . 1 . . C
  H3A 0.2906 0.5447 0.5785 0.100 Uiso calc R 1 . . H
  H3B 0.2866 0.3914 0.5279 0.100 Uiso calc R 1 . . H
  C4 0.3760(5) 0.2625(12) 0.5898(2) 0.0661(18) Uani d . 1 . . C
  C5 0.3667(4) 0.2430(11) 0.6500(2) 0.0564(16) Uani d . 1 . . C
  H5A 0.3689 0.3947 0.6634 0.068 Uiso calc R 1 . . H
  C6 0.4540(4) 0.1252(12) 0.6786(2) 0.0632(17) Uani d . 1 . . C
  H6A 0.4503 -0.0315 0.6710 0.076 Uiso calc R 1 . . H
  H6B 0.5151 0.1805 0.6650 0.076 Uiso calc R 1 . . H
  C7 0.4544(4) 0.1600(12) 0.7378(2) 0.0583(15) Uani d . 1 . . C
  H7A 0.4636 0.3160 0.7451 0.070 Uiso calc R 1 . . H
  H7B 0.5104 0.0824 0.7541 0.070 Uiso calc R 1 . . H
  C8 0.3617(4) 0.0835(9) 0.7642(2) 0.0487(14) Uani d . 1 . . C
  C9 0.2724(3) 0.1806(9) 0.7313(2) 0.0443(13) Uani d . 1 . . C
  H9A 0.2801 0.3406 0.7351 0.053 Uiso calc R 1 . . H
  C10 0.2688(4) 0.1430(10) 0.6707(2) 0.0515(14) Uani d . 1 . . C
  C11 0.1774(4) 0.1302(11) 0.7587(2) 0.0543(14) Uani d . 1 . . C
  H11A 0.1226 0.1898 0.7373 0.065 Uiso calc R 1 . . H
  H11B 0.1689 -0.0285 0.7604 0.065 Uiso calc R 1 . . H
  C12 0.1749(4) 0.2223(9) 0.8136(2) 0.0510(14) Uani d . 1 . . C
  H12A 0.1788 0.3832 0.8106 0.061 Uiso calc R 1 . . H
  C13 0.2620(4) 0.1465(9) 0.8506(2) 0.0454(13) Uani d . 1 . . C
  C14 0.3569(3) 0.1849(8) 0.8205(2) 0.0448(13) Uani d . 1 . . C
  H14A 0.3601 0.3446 0.8149 0.054 Uiso calc R 1 . . H
  C15 0.4472(4) 0.1292(12) 0.8579(2) 0.0580(15) Uani d . 1 . . C
  H15A 0.4410 -0.0205 0.8710 0.070 Uiso calc R 1 . . H
  H15B 0.5066 0.1377 0.8378 0.070 Uiso calc R 1 . . H
  C16 0.4553(4) 0.2832(13) 0.9040(2) 0.0688(18) Uani d . 1 . . C
  H16A 0.4941 0.2140 0.9328 0.083 Uiso calc R 1 . . H
  H16B 0.4900 0.4148 0.8933 0.083 Uiso calc R 1 . . H
  C17 0.3585(5) 0.3473(10) 0.9241(2) 0.0588(15) Uani d . 1 . . C
  C18 0.2732(4) 0.2869(10) 0.9007(2) 0.0553(15) Uani d . 1 . . C
  C19 0.4654(5) 0.410(2) 0.5782(3) 0.104(3) Uani d . 1 . . C
  H19A 0.4630 0.5415 0.5995 0.156 Uiso calc R 1 . . H
  H19B 0.4637 0.4483 0.5410 0.156 Uiso calc R 1 . . H
  H19C 0.5251 0.3310 0.5871 0.156 Uiso calc R 1 . . H
  O20 0.2385(4) 0.4829(9) 0.97577(17) 0.0853(16) Uani d . 1 . . O
  C20 0.3883(6) 0.0506(16) 0.5589(3) 0.093(3) Uani d . 1 . . C
  H20A 0.3270 -0.0282 0.5570 0.140 Uiso calc R 1 . . H
  H20B 0.4379 -0.0389 0.5766 0.140 Uiso calc R 1 . . H
  H20C 0.4079 0.0842 0.5233 0.140 Uiso calc R 1 . . H
  C21 0.3643(4) -0.1683(11) 0.7654(3) 0.0648(17) Uani d . 1 . . C
  H21A 0.4037 -0.2167 0.7959 0.097 Uiso calc R 1 . . H
  H21B 0.3923 -0.2222 0.7333 0.097 Uiso calc R 1 . . H
  H21C 0.2985 -0.2241 0.7678 0.097 Uiso calc R 1 . . H
  C22 0.2500(4) -0.0930(13) 0.6560(2) 0.0716(19) Uani d . 1 . . C
  H22A 0.1997 -0.1517 0.6778 0.107 Uiso calc R 1 . . H
  H22B 0.3095 -0.1766 0.6618 0.107 Uiso calc R 1 . . H
  H22C 0.2288 -0.1021 0.6190 0.107 Uiso calc R 1 . . H
  C23 0.2419(4) -0.0880(11) 0.8692(2) 0.0624(16) Uani d . 1 . . C
  H23A 0.1955 -0.0847 0.8972 0.094 Uiso calc R 1 . . H
  H23B 0.3023 -0.1539 0.8826 0.094 Uiso calc R 1 . . H
  H23C 0.2154 -0.1732 0.8397 0.094 Uiso calc R 1 . . H
  C24 0.3426(6) 0.4677(16) 0.9724(3) 0.087(2) Uani d . 1 . . C
  H24A 0.3713 0.3905 1.0032 0.105 Uiso calc R 1 . . H
  H24B 0.3718 0.6134 0.9707 0.105 Uiso calc R 1 . . H
  C25 0.1974(5) 0.3680(12) 0.9346(2) 0.0670(18) Uani d . 1 . . C
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 0.033(2) 0.110(4) 0.073(3) 0.005(2) 0.0049(17) 0.019(3)
  O2 0.068(3) 0.150(5) 0.068(3) 0.048(3) 0.009(2) 0.020(3)
  C1 0.046(3) 0.071(4) 0.057(4) -0.010(3) -0.014(2) 0.004(3)
  C2 0.062(4) 0.110(6) 0.058(4) -0.014(4) -0.016(3) 0.005(4)
  C3 0.076(5) 0.127(7) 0.047(3) -0.025(5) -0.007(3) -0.002(4)
  C4 0.061(4) 0.091(5) 0.045(3) -0.028(3) -0.005(3) -0.014(3)
  C5 0.039(3) 0.077(4) 0.053(3) -0.013(3) -0.008(2) -0.012(3)
  C6 0.037(3) 0.089(5) 0.063(4) -0.005(3) -0.005(2) -0.003(4)
  C7 0.030(3) 0.084(4) 0.059(4) -0.001(3) -0.011(2) -0.007(3)
  C8 0.030(3) 0.064(4) 0.051(3) 0.003(2) -0.016(2) -0.001(3)
  C9 0.031(3) 0.050(3) 0.050(3) -0.001(2) -0.011(2) 0.002(2)
  C10 0.037(3) 0.059(4) 0.058(3) -0.008(3) -0.013(2) -0.001(3)
  C11 0.034(3) 0.070(4) 0.058(4) -0.007(3) -0.014(2) 0.009(3)
  C12 0.039(3) 0.056(3) 0.058(3) 0.010(2) -0.010(2) 0.016(3)
  C13 0.044(3) 0.048(3) 0.043(3) 0.008(2) -0.012(2) 0.016(2)
  C14 0.041(3) 0.041(3) 0.051(3) 0.005(2) -0.021(2) -0.003(2)
  C15 0.039(3) 0.085(4) 0.049(3) 0.007(3) -0.020(2) -0.005(3)
  C16 0.049(3) 0.101(5) 0.056(4) -0.011(3) -0.013(3) -0.004(4)
  C17 0.074(4) 0.052(3) 0.050(3) -0.002(3) -0.012(3) 0.007(3)
  C18 0.056(3) 0.064(4) 0.046(3) 0.005(3) -0.009(3) 0.012(3)
  C19 0.074(5) 0.181(10) 0.058(4) -0.055(6) 0.011(3) -0.008(5)
  O20 0.108(4) 0.097(4) 0.051(3) 0.035(3) -0.006(2) -0.002(3)
  C20 0.076(5) 0.141(8) 0.062(5) -0.029(5) -0.003(3) -0.032(5)
  C21 0.056(4) 0.063(4) 0.074(4) 0.008(3) -0.015(3) 0.003(3)
  C22 0.050(3) 0.101(6) 0.062(4) -0.020(3) -0.012(3) -0.019(4)
  C23 0.055(3) 0.066(4) 0.065(4) -0.005(3) -0.007(3) 0.013(3)
  C24 0.093(6) 0.115(7) 0.053(4) -0.010(5) -0.009(3) -0.011(4)
  C25 0.073(4) 0.087(5) 0.041(3) 0.027(4) 0.004(3) 0.012(3)
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
  O1 C12 . 1.421(7) ?
  O2 C25 . 1.226(8) ?
  C1 C2 . 1.507(8) ?
  C1 C10 . 1.560(8) ?
  C2 C3 . 1.541(9) ?
  C3 C4 . 1.566(11) ?
  C4 C20 . 1.528(11) ?
  C4 C5 . 1.533(8) y
  C4 C19 . 1.561(9) ?
  C5 C6 . 1.554(8) ?
  C5 C10 . 1.586(8) y
  C6 C7 . 1.508(8) ?
  C7 C8 . 1.534(8) ?
  C8 C21 . 1.543(8) ?
  C8 C14 . 1.555(8) y
  C8 C9 . 1.572(7) y
  C9 C11 . 1.532(7) ?
  C9 C10 . 1.544(8) y
  C10 C22 . 1.513(10) ?
  C11 C12 . 1.500(8) ?
  C12 C13 . 1.559(6) ?
  C13 C18 . 1.533(8) y
  C13 C23 . 1.541(8) ?
  C13 C14 . 1.552(7) y
  C14 C15 . 1.566(7) ?
  C15 C16 . 1.499(9) ?
  C16 C17 . 1.495(9) ?
  C17 C18 . 1.343(8) ?
  C17 C24 . 1.448(9) ?
  C18 C25 . 1.461(8) ?
  O20 C25 . 1.359(8) ?
  O20 C24 . 1.439(9) ?