#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008079.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_2008079
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  91
_journal_page_last  92
_publ_section_title
;
4-Methyl-7,7a,13a,14-tetrahydrobenzo[e]pyrano[2',3':5,6]naphtho[2,3-b]
[1,4]dioxin-2-one
;
loop_
_publ_author_name
  'Kandasamy Chinnakali'
  'Hoong-Kun Fun'
  'Kamaraj Sriraghavan'
  'Vayalakkavoor T.Ramakrishnan'
  'Ibrahim Abdul Razak'
_chemical_formula_sum  'C20 H16 O4'
_chemical_formula_weight  320.33
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'F d d 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z'
  'x+1/4, -y+1/4, z+1/4'
  '-x+1/4, y+1/4, z+1/4'
  'x, y+1/2, z+1/2'
  '-x, -y+1/2, z+1/2'
  'x+1/4, -y+3/4, z+3/4'
  '-x+1/4, y+3/4, z+3/4'
  'x+1/2, y, z+1/2'
  '-x+1/2, -y, z+1/2'
  'x+3/4, -y+1/4, z+3/4'
  '-x+3/4, y+1/4, z+3/4'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, z'
  'x+3/4, -y+3/4, z+1/4'
  '-x+3/4, y+3/4, z+1/4'
_cell_length_a  57.344(2)
_cell_length_b  9.7802(4)
_cell_length_c  10.6263(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  5959.6(4)
_cell_formula_units_Z  16
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.428
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0653
_refine_ls_wR_factor_obs  0.1317
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
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.12393(4) 0.0795(2) 0.3995(2) 0.0389(6) Uani d . 1 . O
  C2 0.14779(6) 0.0791(4) 0.3958(3) 0.0385(8) Uani d . 1 . C
  C3 0.15898(6) 0.2015(4) 0.3494(3) 0.0423(9) Uani d . 1 . C
  H3 0.17517(6) 0.2064(4) 0.3516(3) 0.051 Uiso calc R 1 . H
  C4 0.14702(6) 0.3091(4) 0.3033(3) 0.0387(8) Uani d . 1 . C
  C5 0.10742(7) 0.4107(3) 0.2653(3) 0.0430(9) Uani d . 1 . C
  H5 0.11396(7) 0.4892(3) 0.2307(3) 0.052 Uiso calc R 1 . H
  C6 0.08391(6) 0.4007(4) 0.2742(3) 0.0418(9) Uani d . 1 . C
  H6 0.07468(6) 0.4722(4) 0.2452(3) 0.050 Uiso calc R 1 . H
  C7 0.07313(6) 0.2846(4) 0.3262(3) 0.0371(8) Uani d . 1 . C
  C8 0.08702(6) 0.1777(3) 0.3691(3) 0.0329(8) Uani d . 1 . C
  C9 0.11098(5) 0.1900(3) 0.3572(3) 0.0318(7) Uani d . 1 . C
  C10 0.12216(6) 0.3049(4) 0.3073(3) 0.0361(8) Uani d . 1 . C
  O11 0.15764(4) -0.0222(3) 0.4334(2) 0.0548(8) Uani d . 1 . O
  C12 0.04705(6) 0.2807(4) 0.3387(4) 0.0492(10) Uani d . 1 . C
  H12A 0.04022(6) 0.3052(4) 0.2583(4) 0.059 Uiso calc R 1 . H
  H12B 0.04234(6) 0.3495(4) 0.3993(4) 0.059 Uiso calc R 1 . H
  C13 0.03719(6) 0.1446(4) 0.3792(3) 0.0421(9) Uani d . 1 . C
  H13 0.02150(6) 0.1581(4) 0.4136(3) 0.050 Uiso calc R 1 . H
  C14 0.05222(6) 0.0781(4) 0.4759(3) 0.0420(9) Uani d . 1 . C
  H14 0.05333(6) 0.1395(4) 0.5485(3) 0.050 Uiso calc R 1 . H
  C15 0.07664(6) 0.0508(3) 0.4279(3) 0.0362(8) Uani d . 1 . C
  H15A 0.08642(6) 0.0210(3) 0.4971(3) 0.043 Uiso calc R 1 . H
  H15B 0.07617(6) -0.0220(3) 0.3660(3) 0.043 Uiso calc R 1 . H
  C16 0.15949(7) 0.4317(4) 0.2508(4) 0.0542(10) Uani d . 1 . C
  H16A 0.1545(3) 0.5123(5) 0.2948(17) 0.081 Uiso calc R 1 . H
  H16B 0.1559(4) 0.4408(16) 0.1630(7) 0.081 Uiso calc R 1 . H
  H16C 0.17601(7) 0.4202(13) 0.261(2)  0.081 Uiso calc R 1 . H
  O17 0.04146(4) -0.0493(3) 0.5174(2) 0.0492(7) Uani d . 1 . O
  C18 0.03302(5) -0.1256(4) 0.4192(4) 0.0443(9) Uani d . 1 . C
  C19 0.02740(6) -0.2625(4) 0.4464(5) 0.0609(12) Uani d . 1 . C
  H19 0.02912(6) -0.2971(4) 0.5274(5) 0.073 Uiso calc R 1 . H
  C20 0.01928(7) -0.3442(5) 0.3504(6) 0.075(2) Uani d . 1 . C
  H20 0.01584(7) -0.4354(5) 0.3667(6) 0.090 Uiso calc R 1 . H
  C21 0.01618(8) -0.2940(5) 0.2315(7) 0.077(2) Uani d . 1 . C
  H21 0.01047(8) -0.3506(5) 0.1683(7) 0.093 Uiso calc R 1 . H
  C22 0.02156(7) -0.1586(5) 0.2052(4) 0.0601(12) Uani d . 1 . C
  H22 0.01936(7) -0.1237(5) 0.1246(4) 0.072 Uiso calc R 1 . H
  C23 0.03017(6) -0.0765(4) 0.2995(4) 0.0488(10) Uani d . 1 . C
  O24 0.03583(4) 0.0582(3) 0.2687(2) 0.0496(7) Uani d . 1 . O
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 0.0451(13) 0.0240(14) 0.0475(13) 0.0017(10) 0.0020(11) 0.0058(11)
  C2 0.043(2) 0.038(2) 0.035(2) 0.000(2) 0.001(2) 0.001(2)
  C3 0.039(2) 0.042(2) 0.046(2) -0.008(2) 0.002(2) -0.006(2)
  C4 0.053(2) 0.031(2) 0.032(2) -0.006(2) 0.0013(15) -0.005(2)
  C5 0.063(2) 0.022(2) 0.044(2) -0.006(2) 0.005(2) 0.001(2)
  C6 0.062(2) 0.022(2) 0.042(2) 0.005(2) -0.002(2) 0.004(2)
  C7 0.047(2) 0.024(2) 0.040(2) 0.005(2) -0.003(2) -0.0004(15)
  C8 0.047(2) 0.019(2) 0.032(2) 0.0005(15) -0.0018(14) -0.0005(15)
  C9 0.042(2) 0.022(2) 0.031(2) 0.004(2) 0.0006(15) 0.0001(14)
  C10 0.051(2) 0.023(2) 0.034(2) -0.005(2) -0.001(2) -0.002(2)
  O11 0.055(2) 0.043(2) 0.065(2) 0.0121(13) 0.0003(13) 0.0110(15)
  C12 0.054(2) 0.032(2) 0.061(2) 0.007(2) -0.005(2) 0.005(2)
  C13 0.039(2) 0.034(2) 0.052(2) 0.002(2) 0.001(2) -0.006(2)
  C14 0.048(2) 0.031(2) 0.047(2) -0.008(2) 0.001(2) 0.002(2)
  C15 0.038(2) 0.026(2) 0.045(2) 0.0005(14) -0.0011(15) 0.004(2)
  C16 0.064(3) 0.038(2) 0.061(2) -0.019(2) 0.014(2) 0.000(2)
  O17 0.0498(14) 0.040(2) 0.0580(15) -0.0116(12) 0.0013(13) 0.0098(14)
  C18 0.034(2) 0.036(2) 0.062(2) -0.005(2) 0.000(2) -0.001(2)
  C19 0.041(2) 0.040(2) 0.102(3) -0.005(2) 0.001(2) 0.009(3)
  C20 0.049(3) 0.032(3) 0.144(5) -0.003(2) 0.003(3) -0.014(3)
  C21 0.052(3) 0.055(3) 0.126(5) -0.007(2) 0.005(3) -0.044(3)
  C22 0.051(2) 0.061(3) 0.068(3) -0.007(2) 0.003(2) -0.021(2)
  C23 0.040(2) 0.039(2) 0.068(3) -0.003(2) 0.002(2) -0.011(2)
  O24 0.058(2) 0.040(2) 0.0502(14) -0.0052(12) -0.0054(13) 0.0010(13)
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 C2 . 1.369(4) ?
  O1 C9 . 1.386(4) ?
  C2 O11 . 1.208(4) ?
  C2 C3 . 1.445(5) ?
  C3 C4 . 1.348(5) yes
  C4 C10 . 1.427(5) ?
  C4 C16 . 1.504(5) ?
  C5 C6 . 1.355(5) yes
  C5 C10 . 1.409(5) ?
  C6 C7 . 1.406(5) ?
  C7 C8 . 1.391(5) ?
  C7 C12 . 1.502(5) yes
  C8 C9 . 1.385(4) ?
  C8 C15 . 1.512(4) yes
  C9 C10 . 1.398(5) ?
  C12 C13 . 1.509(5) yes
  C13 O24 . 1.448(4) yes
  C13 C14 . 1.491(5) yes
  C14 O17 . 1.459(4) yes
  C14 C15 . 1.514(5) yes
  O17 C18 . 1.371(5) yes
  C18 C23 . 1.369(6) ?
  C18 C19 . 1.407(6) ?
  C19 C20 . 1.377(7) ?
  C20 C21 . 1.367(7) ?
  C21 C22 . 1.389(7) ?
  C22 C23 . 1.376(6) ?
  C23 O24 . 1.395(5) ?