#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008184.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_2008184
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_publ_section_title
;
Two 3-substituted 5-nitroindoles
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Garcia, J. Gabriel'
  'Billodeaux, Damon R.'
  'Fronczek, Frank R.'
_chemical_formula_moiety  'C11 H12 N2 O3'
_chemical_formula_sum  'C11 H12 N2 O3'
_chemical_formula_iupac  'C11 H12 N2 O3'
_chemical_formula_weight  220.2
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,1/2+y,1/2-z'
  '-x,-y,-z'
  '+x,1/2-y,1/2+z'
_cell_length_a  10.3272(7)
_cell_length_b  13.9620(10)
_cell_length_c  7.4435(6)
_cell_angle_alpha  90
_cell_angle_beta  99.489(6)
_cell_angle_gamma  90
_cell_volume  1058.6(3)
_cell_formula_units_z  4
_cell_measurement_temperature  299
_exptl_crystal_density_diffrn  1.382
_diffrn_ambient_temperature  299
_refine_ls_R_factor_obs  0.047
_refine_ls_wR_factor_obs  0.056
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_calc_attached_atom
_atom_site_type_symbol
  O1 0.31300(10)
  0.58090(8) 0.3046(2) 0.0647(7) Uij ? ? O
  O2 0.23690(10)
  0.43943(9) 0.3313(2) 0.0682(7) Uij ? ? O
  O3 1.07230(10)
  0.67467(8) 0.3020(2) 0.0629(7) Uij ? ? O
  N1 0.80250(10)
  0.35725(9) 0.1770(2) 0.0550(7) Uij ? ? N
  N2 0.32610(10)
  0.49344(9) 0.3067(2) 0.0485(6) Uij ? ? N
  C1 0.8608(2) 0.44210(10)
  0.1397(2) 0.0552(8) Uij ? ? C
  C2 0.77940(10)
  0.51740(10)
  0.1519(2) 0.0438(7) Uij ? ? C
  C3 0.66250(10)
  0.47680(10)
  0.2019(2) 0.0392(6) Uij ? ? C
  C4 0.68120(10)
  0.37630(10)
  0.2159(2) 0.0443(7) Uij ? ? C
  C5 0.5851(2) 0.31470(10)
  0.2618(2) 0.0514(8) Uij ? ? C
  C6 0.46910(10)
  0.35420(10)
  0.2925(2) 0.0506(8) Uij ? ? C
  C7 0.45070(10)
  0.45380(10)
  0.2773(2) 0.0427(7) Uij ? ? C
  C8 0.54430(10)
  0.51570(10)
  0.2331(2) 0.0394(6) Uij ? ? C
  C9 0.80420(10)
  0.62130(10)
  0.1224(2) 0.0485(7) Uij ? ? C
  C10 0.84150(10)
  0.67850(10)
  0.2977(2) 0.0469(7) Uij ? ? C
  C11 0.9713(2) 0.65090(10)
  0.4044(2) 0.0542(9) Uij ? ? C
  H3O 1.138(2) 0.635(2) 0.313(3) 0.110(7) Uiso ? ? H
  H1N 0.838(2) 0.2990(10)
  0.176(2) 0.087(6) Uiso ? ? H
  H1 0.951(2) 0.4440(10)
  0.109(2) 0.071(5) Uiso ? ? H
  H5 0.603(2) 0.2490(10)
  0.270(2) 0.081(6) Uiso ? ? H
  H6 0.403(2) 0.3140(10)
  0.323(2) 0.077(6) Uiso ? ? H
  H8 0.5250(10)
  0.5850(10)
  0.224(2) 0.060(5) Uiso ? ? H
  H9a 0.725(2) 0.6500(10)
  0.051(2) 0.069(5) Uiso ? ? H
  H9b 0.8750(10)
  0.6280(10)
  0.050(2) 0.059(5) Uiso ? ? H
  H10a 0.772(2) 0.6710(10)
  0.382(2) 0.063(5) Uiso ? ? H
  H10b 0.844(2) 0.7490(10)
  0.265(2) 0.065(5) Uiso ? ? H
  H11a 0.987(2) 0.6860(10)
  0.527(3) 0.099(7) Uiso ? ? H
  H11b 0.9780(10)
  0.5820(10)
  0.429(2) 0.068(5) Uiso ? ? 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
_atom_site_aniso_type_symbol
  O1 0.0483(5) 0.0520(6) 0.1079(9) 0.0080(5) 0.0214(6) -0.0062(6) O
  O2 0.0490(5) 0.0728(8) 0.0892(8) -0.0124(5) 0.0252(5) 0.0014(6) O
  O3 0.0386(5) 0.0483(6) 0.1340(10)
  0.0019(5) 0.0176(6) 0.0104(7) O
  N1 0.0485(6) 0.0416(6) 0.0823(9) 0.0104(5) 0.0134(6) -0.0056(6) N
  N2 0.0396(6) 0.0513(7) 0.0560(6) -0.0016(5) 0.0096(5) -0.0035(6) N
  C1 0.0444(7) 0.0531(9) 0.0714(9) 0.0041(7) 0.0177(7) -0.0043(7) C
  C2 0.0390(6) 0.0442(7) 0.0487(7) 0.0007(6) 0.0091(5) -0.0017(6) C
  C3 0.0382(6) 0.0360(6) 0.0437(6) 0.0011(5) 0.0041(5) -0.0021(5) C
  C4 0.0415(7) 0.0367(7) 0.0572(8) 0.0044(6) 0.0038(6) -0.0051(6) C
  C5 0.0543(8) 0.0310(7) 0.0810(10)
  -0.0009(6) 0.0048(8) -0.0017(7) C
  C6 0.0475(7) 0.0387(7) 0.0710(10)
  -0.0083(6) 0.0072(7) 0.0007(7) C
  C7 0.0378(6) 0.0412(7) 0.0501(7) -0.0011(6) 0.0063(6) -0.0035(6) C
  C8 0.0387(6) 0.0344(6) 0.0459(7) 0.0019(5) 0.0054(5) -0.0017(6) C
  C9 0.0444(7) 0.0471(7) 0.0544(8) -0.0019(6) 0.0111(6) 0.0064(7) C
  C10 0.0413(6) 0.0401(7) 0.0623(8) 0.0008(6) 0.0155(6) 0.0011(6) C
  C11 0.0533(8) 0.0432(8) 0.0690(10)
  -0.0039(7) 0.0022(8) 0.0013(7) C
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 N2 . . 1.228(2) yes
  O2 N2 . . 1.227(2) yes
  O3 C11 . . 1.428(2) yes
  O3 H3O . . 0.87(2) ?
  N1 C1 . . 1.378(2) yes
  N1 C4 . . 1.358(2) yes
  N1 H1N . . 0.89(2) ?
  N2 C7 . . 1.451(2) ?
  C1 C2 . . 1.359(2) yes
  C1 H1 . . 0.99(2) ?
  C2 C3 . . 1.438(2) ?
  C2 C9 . . 1.494(2) ?
  C3 C4 . . 1.417(2) ?
  C3 C8 . . 1.390(2) ?
  C4 C5 . . 1.398(2) ?
  C5 C6 . . 1.372(2) ?
  C5 H5 . . 0.94(2) ?
  C6 C7 . . 1.405(2) ?
  C6 H6 . . 0.94(2) ?
  C7 C8 . . 1.376(2) ?
  C8 H8 . . 0.99(2) ?
  C9 C10 . . 1.525(2) ?
  C9 H9a . . 0.98(2) ?
  C9 H9b . . 0.98(2) ?
  C10 C11 . . 1.492(2) ?
  C10 H10a . . 1.04(2) ?
  C10 H10b . . 1.01(2) ?
  C11 H11a . . 1.03(2) ?
  C11 H11b . . 0.98(2) ?