#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009021.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_2009021
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1698
_journal_page_last  1701
_publ_section_title
;
6,7,8,9-Tetrahydro-3-methyl-1H-pyrano[4,3-b]quinoline-1-one
;
loop_
_publ_author_name
  'Hua, Duy H.'
  'Chen, Yi'
  'Sin, Hong-Sig'
  'Robinson, Paul D.'
  'Meyers, Cal Y.'
  'Perchellet, Elisabeth M.'
  'Perchellet, Jean-Pierre'
  'Chiang, Peter K.'
  'Biellmann, Jean-Francois'
_chemical_formula_moiety  'C13 H13 N O2'
_chemical_formula_sum  'C13 H13 N O2'
_chemical_formula_weight  215.24
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.6535(9)
_cell_length_b  10.8255(10)
_cell_length_c  7.4067(9)
_cell_angle_alpha  92.436(10)
_cell_angle_beta  117.023(8)
_cell_angle_gamma  81.610(9)
_cell_volume  540.62(10)
_cell_formula_units_Z  2
_cell_measurement_temperature  296
_exptl_crystal_density_diffrn  1.322
_diffrn_ambient_temperature  296
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  .2678(4)  .6380(2)  .1424(4)  .0521(7) Uani d . 1 . . C
  O2  .2435(2)  .72127(15)  .2777(3)  .0564(5) Uani d . 1 . . O
  C3  .2146(4)  .6840(2)  .4378(4)  .0502(6) Uani d . 1 . . C
  C4  .2101(4)  .5658(2)  .4686(4)  .0539(7) Uani d . 1 . . C
  C4a  .2325(3)  .4711(2)  .3358(4)  .0476(6) Uani d . 1 . . C
  N5  .2253(3)  .3511(2)  .3706(3)  .0594(6) Uani d . 1 . . N
  C5a  .2465(4)  .2657(2)  .2429(4)  .0555(7) Uani d . 1 . . C
  C6  .2332(5)  .1336(2)  .2860(5)  .0815(10) Uani d . 1 . . C
  C7  .3094(5)  .0362(2)  .1769(5)  .0776(9) Uani d . 1 . . C
  C8  .2276(4)  .0742(3)  -.0434(5)  .0753(9) Uani d . 1 . . C
  C9  .2983(4)  .1939(2)  -.0628(4)  .0630(8) Uani d . 1 . . C
  C9a  .2744(3)  .2942(2)  .0749(4)  .0501(7) Uani d . 1 . . C
  C10  .2829(3)  .4173(2)  .0458(4)  .0495(6) Uani d . 1 . . C
  C10a  .2612(3)  .5077(2)  .1742(3)  .0430(6) Uani d . 1 . . C
  O11  .2904(3)  .68089(17)  .0082(3)  .0777(7) Uani d . 1 . . O
  C12  .1939(4)  .7934(2)  .5587(4)  .0706(8) Uani d . 1 . . C
  H4  .1921  .5432  .5782  .065 Uiso calc R 1 . . H
  H6a  .0959  .1264  .2474  .098 Uiso calc R 1 . . H
  H6b  .3081  .1163  .4308  .098 Uiso calc R 1 . . H
  H7a  .4530  .0265  .2404  .093 Uiso calc R 1 . . H
  H7b  .2703  -.0435  .1870  .093 Uiso calc R 1 . . H
  H8a  .0840  .0860  -.1060  .090 Uiso calc R 1 . . H
  H8b  .2705  .0084  -.1136  .090 Uiso calc R 1 . . H
  H9a  .4371  .1760  -.0320  .076 Uiso calc R 1 . . H
  H9b  .2248  .2250  -.2021  .076 Uiso calc R 1 . . H
  H10  .3035  .4400  -.0619  .059 Uiso calc R 1 . . H
  H12a  .0768  .8497  .4763  .106 Uiso calc R 1 . . H
  H12b  .3079  .8357  .6035  .106 Uiso calc R 1 . . H
  H12c  .1835  .7654  .6743  .106 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
  C1  .0554(17)  .0477(15)  .0584(17)  -.0068(12)  .0303(15)  .0003(14)
  O2  .0696(13)  .0450(10)  .0625(11)  -.0072(8)  .0370(10)  -.0029(9)
  C3  .0493(16)  .0535(16)  .0464(16)  -.0061(12)  .0208(14)  -.0019(13)
  C4  .0568(18)  .0647(18)  .0449(15)  -.0057(13)  .0277(14)  .0034(13)
  C4a  .0467(16)  .0438(14)  .0538(17)  -.0034(12)  .0245(14)  .0047(12)
  N5  .0729(16)  .0495(13)  .0667(15)  -.0039(11)  .0418(14)  .0065(11)
  C5a  .0522(17)  .0454(15)  .0744(19)  -.0028(12)  .0337(15)  .0079(13)
  C6  .099(3)  .0495(17)  .115(3)  -.0109(16)  .064(2)  .0081(17)
  C7  .077(2)  .0409(15)  .121(3)  -.0097(14)  .049(2)  -.0001(17)
  C8  .066(2)  .0520(17)  .107(3)  -.0134(14)  .0384(19)  -.0184(17)
  C9  .0601(18)  .0553(17)  .071(2)  -.0067(13)  .0293(16)  -.0134(14)
  C9a  .0439(16)  .0442(15)  .0626(18)  -.0043(12)  .0250(14)  -.0016(13)
  C10  .0467(16)  .0526(15)  .0526(16)  -.0029(12)  .0260(14)  .0050(12)
  C10a  .0391(14)  .0448(14)  .0466(15)  -.0024(10)  .0212(13)  .0035(12)
  O11  .1187(18)  .0582(12)  .0873(15)  -.0139(11)  .0723(14)  .0066(10)
  C12  .079(2)  .0651(19)  .0634(19)  -.0080(15)  .0304(17)  -.0142(15)
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
  O11 C1 . 1.206(3) yes
  C3 C4 . 1.318(3) yes
  N5 C4a . 1.349(3) yes
  C3 C12 . 1.488(3) yes
  O2 C3 . 1.387(3) yes
  C4 C4a . 1.436(3) yes
  N5 C5a . 1.341(3) yes
  C1 C10a . 1.451(3) yes
  O2 C1 . 1.376(3) no
  C4a C10a . 1.394(3) no
  C5a C9a . 1.408(3) no
  C5a C6 . 1.506(3) no
  C6 C7 . 1.510(3) no
  C7 C8 . 1.509(4) no
  C8 C9 . 1.512(3) no
  C9 C9a . 1.507(3) no
  C9a C10 . 1.374(3) no
  C10 C10a . 1.381(3) no
  C4 H4 .  .9300 no
  C6 H6a .  .9700 no
  C6 H6b .  .9700 no
  C7 H7a .  .9700 no
  C7 H7b .  .9700 no
  C8 H8a .  .9700 no
  C8 H8b .  .9700 no
  C9 H9a .  .9700 no
  C9 H9b .  .9700 no
  C10 H10 .  .9300 no
  C12 H12a .  .9600 no
  C12 H12b .  .9600 no
  C12 H12c .  .9600 no