#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006520.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_2006520
_journal_name_full 'Acta Crystallographica Section C'
_journal_year   1997
_journal_volume 53
_journal_page_first   1362
_journal_page_last   1363
_publ_section_title
;
cis-6,10b,11,12-Tetrahydro-12-hydroxypyrrolo[1',2':2,3]pyridazino[6,1-a]
isoindole-6-one
;
loop_
_publ_author_name
  "Ko\<z\'i\<sek, Jozef"
  '   Ingrid Svoboda'
  "   \<Stefan Marchal\'in "
  '   Bernard Decroix'
_chemical_formula_sum   'C14 H12 N2 O2'
_chemical_formula_weight   240.26
_symmetry_cell_setting   monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall   '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a   8.386(2)
_cell_length_b   8.149(2)
_cell_length_c   17.267(4)
_cell_angle_alpha   90.00
_cell_angle_beta   99.04(4)
_cell_angle_gamma   90.00
_cell_volume   1165.3(5)
_cell_formula_units_Z   4
_cell_measurement_temperature   298(2)
_exptl_crystal_density_diffrn   1.369
_diffrn_ambient_temperature   298(2)
_refine_ls_R_factor_obs  .0325
_refine_ls_wR_factor_obs  .0843
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  .22906(14)  .0062(2)  .33126(8)  .0751(4) Uani d . 1 . O
  O2  .5967(2)  .4433(2)  .16316(7)  .0628(4) Uani d . 1 . O
  H21  .493(3)  .465(3)  .1577(13)  .096(8) Uiso d . 1 . H
  N1  .4783(2)  .0553(2)  .23782(8)  .0514(4) Uani d . 1 . N
  N2  .48472(15)  .0889(2)  .31696(7)  .0486(4) Uani d . 1 . N
  C1  .5235(2)  .0801(3)  .11720(11)  .0656(5) Uani d . 1 . C
  H1  .5548(2)  .1204(3)  .07148(11)  .079 Uiso calc R 1 . H
  C2  .4492(2)  -.0714(3)  .12522(13)  .0764(6) Uani d . 1 . C
  H2  .4222(2)  -.1485(3)  .08565(13)  .092 Uiso calc R 1 . H
  C3  .4234(2)  -.0866(2)  .20057(12)  .0673(5) Uani d . 1 . C
  H3  .3775(2)  -.1757(2)  .22247(12)  .081 Uiso calc R 1 . H
  C4  .3562(2)  .0749(2)  .35662(10)  .0531(4) Uani d . 1 . C
  C5  .3375(2)  .1602(2)  .49956(12)  .0680(6) Uani d . 1 . C
  H5  .2386(2)  .1097(2)  .50114(12)  .082 Uiso calc R 1 . H
  C6  .4184(3)  .2426(3)  .56392(12)  .0771(6) Uani d . 1 . C
  H6  .3725(3)  .2479(3)  .60952(12)  .093 Uiso calc R 1 . H
  C7  .5655(3)  .3172(3)  .56222(11)  .0729(6) Uani d . 1 . C
  H7  .6176(3)  .3706(3)  .60670(11)  .087 Uiso calc R 1 . H
  C8  .6356(2)  .3136(2)  .49552(10)  .0602(5) Uani d . 1 . C
  H8A  .7343(2)  .3647(2)  .49422(10)  .072 Uiso calc R 1 . H
  C9  .5565(2)  .2323(2)  .43036(9)  .0481(4) Uani d . 1 . C
  C10  .6071(2)  .2070(2)  .35190(9)  .0455(4) Uani d . 1 . C
  H10  .7153(2)  .1586(2)  .35760(9)  .055 Uiso calc R 1 . H
  C11  .5957(2)  .3579(2)  .29906(9)  .0478(4) Uani d . 1 . C
  H11A  .4887(2)  .4054(2)  .29521(9)  .057 Uiso calc R 1 . H
  H11B  .6734(2)  .4394(2)  .32193(9)  .057 Uiso calc R 1 . H
  C12  .6286(2)  .3130(2)  .21769(9)  .0490(4) Uani d . 1 . C
  H12  .7444(2)  .2896(2)  .22274(9)  .059 Uiso calc R 1 . H
  C13  .5422(2)  .1590(2)  .18791(9)  .0484(4) Uani d . 1 . C
  C14  .4095(2)  .1555(2)  .43232(10)  .0526(4) 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  .0459(7)  .0778(9)  .0991(10)  -.0133(6)  .0035(7)  .0122(8)
  O2  .0534(8)  .0688(8)  .0693(8)  -.0053(6)  .0189(6)  .0146(6)
  N1  .0485(8)  .0492(8)  .0536(8)  -.0044(6)  -.0010(6)  -.0062(6)
  N2  .0445(7)  .0485(8)  .0516(8)  -.0061(6)  .0034(6)  -.0010(6)
  C1  .0527(10)  .0871(14)  .0548(11)  -.0028(10)  .0015(8)  -.0135(10)
  C2  .0702(13)  .0809(14)  .0721(14)  -.0079(11)  -.0082(10)  -.0287(11)
  C3  .0632(11)  .0537(11)  .0783(13)  -.0104(9)  -.0099(9)  -.0115(10)
  C4  .0390(9)  .0485(10)  .0707(11)  .0015(8)  .0054(8)  .0144(8)
  C5  .0613(11)  .0702(13)  .0772(14)  .0247(10)  .0257(10)  .0276(11)
  C6  .099(2)  .0790(14)  .0597(12)  .0419(13)  .0310(11)  .0180(11)
  C7  .094(2)  .0707(13)  .0540(11)  .0265(12)  .0125(10)  .0019(9)
  C8  .0660(11)  .0598(11)  .0535(11)  .0113(9)  .0049(8)  -.0028(9)
  C9  .0460(9)  .0478(9)  .0501(9)  .0119(7)  .0059(7)  .0031(7)
  C10  .0339(8)  .0477(9)  .0536(9)  .0010(7)  .0028(6)  -.0059(7)
  C11  .0410(8)  .0462(9)  .0570(10)  -.0037(7)  .0098(7)  -.0053(7)
  C12  .0339(8)  .0567(10)  .0575(10)  -.0006(7)  .0107(7)  -.0006(8)
  C13  .0349(8)  .0567(10)  .0523(9)  .0024(7)  .0031(7)  -.0043(8)
  C14  .0468(9)  .0522(10)  .0601(10)  .0145(8)  .0118(8)  .0144(8)
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 C4 . 1.223(2) ?
  O2 C12 . 1.416(2) ?
  O2 H21 .  .87(2) ?
  N1 C3 . 1.367(2) ?
  N1 C13 . 1.375(2) ?
  N1 N2 . 1.386(2) ?
  N2 C4 . 1.370(2) ?
  N2 C10 . 1.466(2) ?
  C1 C13 . 1.367(2) ?
  C1 C2 . 1.399(3) ?
  C1 H1 .  .93 ?
  C2 C3 . 1.358(3) ?
  C2 H2 .  .93 ?
  C3 H3 .  .93 ?
  C4 C14 . 1.469(3) ?
  C5 C6 . 1.382(3) ?
  C5 C14 . 1.391(2) ?
  C5 H5 .  .93 ?
  C6 C7 . 1.380(3) ?
  C6 H6 .  .93 ?
  C7 C8 . 1.373(3) ?
  C7 H7 .  .93 ?
  C8 C9 . 1.382(2) ?
  C8 H8A .  .93 ?
  C9 C14 . 1.387(2) ?
  C9 C10 . 1.497(2) ?
  C10 C11 . 1.525(2) ?
  C10 H10 .  .98 ?
  C11 C12 . 1.519(2) ?
  C11 H11A .  .97 ?
  C11 H11B .  .97 ?
  C12 C13 . 1.499(2) ?
  C12 H12 .  .98 ?