#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012973.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_2012973
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o606
_journal_page_last  o607
_publ_section_title
;
6-Acetonyldihydroavicine
;
loop_
_publ_author_name
  'Morel, Ademir F.'
  'Gonzaga, Wellington de A.'
  'Burrow, Robert A.'
  'Maichle-M\"ossmer, C\"acilia'
  'Str\"ahle, Johannes'
_chemical_name_common
;
6-acetonyldihydroavicine
;
_chemical_formula_moiety  'C23 H19 N O5'
_chemical_formula_sum  'C23 H19 N O5'
_chemical_formula_iupac  'C23 H19 N O5'
_chemical_formula_weight  389.39
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.2525(7)
_cell_length_b  8.2653(6)
_cell_length_c  13.9594(6)
_cell_angle_alpha  94.191(6)
_cell_angle_beta  93.879(6)
_cell_angle_gamma  105.293(6)
_cell_volume  912.25(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  213(2)
_exptl_crystal_density_diffrn  1.419
_diffrn_ambient_temperature  213(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
  C1 0.9251(2) 0.4457(2) 0.26085(15) 0.0364(5) Uani d . 1 . . C
  C2 0.9819(3) 0.6139(2) 0.30341(16) 0.0403(5) Uani d . 1 . . C
  H2 1.0524 0.6958 0.2705 0.048 Uiso calc R 1 . . H
  C3 0.9362(3) 0.6592(2) 0.39108(16) 0.0415(5) Uani d . 1 . . C
  H3 0.9786 0.7713 0.4182 0.050 Uiso calc R 1 . . H
  C4 0.8266(2) 0.5420(2) 0.44253(16) 0.0385(5) Uani d . 1 . . C
  C5 0.7771(3) 0.5901(3) 0.53340(16) 0.0438(5) Uani d . 1 . . C
  H5 0.8162 0.7016 0.5619 0.053 Uiso calc R 1 . . H
  C6 0.6722(3) 0.4705(3) 0.57735(16) 0.0435(5) Uani d . 1 . . C
  O7 0.6093(2) 0.4861(2) 0.66507(12) 0.0593(5) Uani d . 1 . . O
  C8 0.4987(3) 0.3258(3) 0.67673(17) 0.0521(6) Uani d . 1 . . C
  H8A 0.3833 0.3351 0.6802 0.063 Uiso calc R 1 . . H
  H8B 0.5338 0.2845 0.7366 0.063 Uiso calc R 1 . . H
  O9 0.5051(2) 0.2119(2) 0.59622(12) 0.0597(5) Uani d . 1 . . O
  C10 0.6093(3) 0.3045(3) 0.53547(16) 0.0429(5) Uani d . 1 . . C
  C11 0.6499(3) 0.2506(3) 0.44921(16) 0.0414(5) Uani d . 1 . . C
  H11 0.6058 0.1384 0.4225 0.050 Uiso calc R 1 . . H
  C12 0.7636(2) 0.3726(2) 0.40005(15) 0.0368(5) Uani d . 1 . . C
  C13 0.8160(2) 0.3272(2) 0.30921(15) 0.0357(5) Uani d . 1 . . C
  N14 0.75781(19) 0.15470(19) 0.27038(12) 0.0355(4) Uani d . 1 . . N
  C15 0.7375(2) 0.1346(2) 0.16421(15) 0.0359(5) Uani d . 1 . . C
  H15 0.7260 0.0145 0.1439 0.043 Uiso calc R 1 . . H
  C16 0.8894(2) 0.2369(2) 0.11996(15) 0.0362(5) Uani d . 1 . . C
  C17 0.9359(2) 0.1753(3) 0.03309(16) 0.0390(5) Uani d . 1 . . C
  H17 0.8728 0.0725 0.0000 0.047 Uiso calc R 1 . . H
  C18 1.0772(2) 0.2715(3) -0.00166(16) 0.0390(5) Uani d . 1 . . C
  O19 1.14947(19) 0.23701(18) -0.08428(11) 0.0518(4) Uani d . 1 . . O
  C20 1.3022(3) 0.3695(3) -0.08225(17) 0.0469(6) Uani d . 1 . . C
  H20A 1.3999 0.3235 -0.0755 0.056 Uiso calc R 1 . . H
  H20B 1.3052 0.4235 -0.1426 0.056 Uiso calc R 1 . . H
  O21 1.30803(18) 0.48984(18) -0.00258(11) 0.0493(4) Uani d . 1 . . O
  C22 1.1708(2) 0.4225(2) 0.04670(15) 0.0367(5) Uani d . 1 . . C
  C23 1.1264(2) 0.4872(2) 0.13053(15) 0.0374(5) Uani d . 1 . . C
  H23 1.1897 0.5918 0.1616 0.045 Uiso calc R 1 . . H
  C24 0.9815(2) 0.3910(2) 0.16891(15) 0.0352(5) Uani d . 1 . . C
  C25 0.8613(3) 0.0526(3) 0.31112(16) 0.0440(5) Uani d . 1 . . C
  H25A 0.9765 0.0944 0.2950 0.066 Uiso calc R 1 . . H
  H25B 0.8166 -0.0638 0.2846 0.066 Uiso calc R 1 . . H
  H25C 0.8593 0.0596 0.3807 0.066 Uiso calc R 1 . . H
  C26 0.5723(2) 0.1717(3) 0.12994(17) 0.0405(5) Uani d . 1 . . C
  H26A 0.5716 0.2842 0.1571 0.048(6) Uiso calc R 1 . . H
  H26B 0.5624 0.1696 0.0595 0.065(8) Uiso calc R 1 . . H
  C27 0.4248(2) 0.0414(3) 0.16143(16) 0.0399(5) Uani d . 1 . . C
  C28 0.3008(3) 0.1003(3) 0.2164(2) 0.0683(8) Uani d . 1 . . C
  H28A 0.2119 0.0040 0.2301 0.102 Uiso calc R 1 . . H
  H28B 0.2524 0.1728 0.1786 0.102 Uiso calc R 1 . . H
  H28C 0.3566 0.1626 0.2765 0.102 Uiso calc R 1 . . H
  O29 0.41039(18) -0.10772(18) 0.14154(12) 0.0524(4) 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
  C1 0.0304(10) 0.0332(10) 0.0447(13) 0.0073(8) 0.0012(9) 0.0047(9)
  C2 0.0345(10) 0.0317(10) 0.0529(14) 0.0049(8) 0.0045(9) 0.0065(9)
  C3 0.0382(11) 0.0308(10) 0.0525(14) 0.0061(9) 0.0001(10) 0.0006(9)
  C4 0.0329(10) 0.0369(11) 0.0462(13) 0.0108(9) 0.0014(9) 0.0040(9)
  C5 0.0426(12) 0.0398(12) 0.0483(14) 0.0123(10) 0.0007(10) -0.0003(10)
  C6 0.0395(12) 0.0509(13) 0.0426(13) 0.0168(10) 0.0047(10) 0.0031(10)
  O7 0.0691(11) 0.0592(10) 0.0498(11) 0.0150(9) 0.0184(8) 0.0026(8)
  C8 0.0535(14) 0.0632(15) 0.0425(14) 0.0179(12) 0.0128(11) 0.0082(11)
  O9 0.0710(12) 0.0548(10) 0.0510(11) 0.0072(9) 0.0280(9) 0.0051(8)
  C10 0.0379(11) 0.0461(12) 0.0454(14) 0.0096(10) 0.0078(10) 0.0105(10)
  C11 0.0376(11) 0.0392(11) 0.0473(13) 0.0087(9) 0.0080(10) 0.0060(9)
  C12 0.0320(10) 0.0355(11) 0.0435(13) 0.0100(8) 0.0013(9) 0.0056(9)
  C13 0.0302(10) 0.0316(10) 0.0444(13) 0.0076(8) -0.0001(9) 0.0043(9)
  N14 0.0330(9) 0.0290(8) 0.0433(10) 0.0061(7) 0.0028(7) 0.0049(7)
  C15 0.0317(10) 0.0307(10) 0.0422(12) 0.0020(8) 0.0050(9) 0.0058(8)
  C16 0.0295(10) 0.0331(10) 0.0453(13) 0.0060(8) 0.0041(9) 0.0073(9)
  C17 0.0324(10) 0.0347(10) 0.0460(13) 0.0019(8) 0.0043(9) 0.0039(9)
  C18 0.0357(11) 0.0375(11) 0.0440(13) 0.0081(9) 0.0081(9) 0.0067(9)
  O19 0.0490(9) 0.0438(9) 0.0555(10) -0.0025(7) 0.0216(8) -0.0002(7)
  C20 0.0415(12) 0.0420(12) 0.0538(15) 0.0029(10) 0.0141(10) 0.0052(10)
  O21 0.0420(8) 0.0423(8) 0.0584(11) -0.0009(7) 0.0214(7) 0.0023(7)
  C22 0.0289(10) 0.0350(10) 0.0457(13) 0.0045(8) 0.0076(9) 0.0115(9)
  C23 0.0305(10) 0.0319(10) 0.0468(13) 0.0028(8) 0.0026(9) 0.0063(9)
  C24 0.0294(10) 0.0317(10) 0.0432(12) 0.0054(8) 0.0024(9) 0.0063(9)
  C25 0.0457(12) 0.0376(11) 0.0507(14) 0.0139(9) 0.0025(10) 0.0086(9)
  C26 0.0315(10) 0.0382(11) 0.0484(14) 0.0024(9) 0.0035(9) 0.0088(9)
  C27 0.0312(11) 0.0392(12) 0.0469(13) 0.0054(9) -0.0014(9) 0.0089(9)
  C28 0.0549(15) 0.0610(16) 0.095(2) 0.0176(13) 0.0324(15) 0.0157(15)
  O29 0.0429(9) 0.0365(9) 0.0707(12) -0.0013(7) 0.0045(8) 0.0040(7)
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
  C1 C13 . 1.393(3) n
  C1 C2 . 1.415(3) n
  C1 C24 . 1.475(3) y
  C2 C3 . 1.360(3) n
  C3 C4 . 1.414(3) n
  C4 C5 . 1.420(3) n
  C4 C12 . 1.427(3) n
  C5 C6 . 1.347(3) n
  C6 O7 . 1.373(3) y
  C6 C10 . 1.400(3) y
  O7 C8 . 1.424(3) y
  C8 O9 . 1.425(3) y
  O9 C10 . 1.375(3) y
  C10 C11 . 1.347(3) n
  C11 C12 . 1.435(3) n
  C12 C13 . 1.423(3) n
  C13 N14 . 1.431(2) y
  N14 C25 . 1.466(2) y
  N14 C15 . 1.472(3) y
  C15 C16 . 1.513(3) n
  C15 C26 . 1.528(3) n
  C16 C17 . 1.397(3) n
  C16 C24 . 1.400(3) y
  C17 C18 . 1.368(3) n
  C18 O19 . 1.379(2) y
  C18 C22 . 1.381(3) y
  O19 C20 . 1.432(2) y
  C20 O21 . 1.426(3) y
  O21 C22 . 1.377(2) y
  C22 C23 . 1.364(3) n
  C23 C24 . 1.413(3) n
  C26 C27 . 1.511(3) n
  C27 O29 . 1.216(2) n
  C27 C28 . 1.479(3) n
  C2 H2 . 0.9400 ?
  C3 H3 . 0.9400 ?
  C5 H5 . 0.9400 ?
  C8 H8A . 0.9800 ?
  C8 H8B . 0.9800 ?
  C11 H11 . 0.9400 ?
  C15 H15 . 0.9900 ?
  C17 H17 . 0.9400 ?
  C20 H20A . 0.9800 ?
  C20 H20B . 0.9800 ?
  C23 H23 . 0.9400 ?
  C25 H25A . 0.9700 ?
  C25 H25B . 0.9700 ?
  C25 H25C . 0.9700 ?
  C26 H26A . 0.9800 ?
  C26 H26B . 0.9800 ?
  C28 H28A . 0.9700 ?
  C28 H28B . 0.9700 ?
  C28 H28C . 0.9700 ?