data_2008183
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_publ_section_title
;
Two 3-substituted 5-nitroindoles
;
loop_
_publ_author_name
  'Garcia, J. Gabriel'
  'Billodeaux, Damon R.'
  'Fronczek, Frank R.'
_chemical_formula_moiety  'C11 H11 Br N2 O2'
_chemical_formula_sum  'C11 H11 Br N2 O2'
_chemical_formula_iupac  'C11 H11 Br N2 O2'
_chemical_formula_weight  283.1
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2y1'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  '-x,1/2+y,-z'
_cell_length_a  5.2326(3)
_cell_length_b  16.766(2)
_cell_length_c  6.6130(5)
_cell_angle_alpha  90
_cell_angle_beta  106.983(5)
_cell_angle_gamma  90
_cell_volume  554.90(10)
_cell_formula_units_z  2
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.694
_diffrn_ambient_temperature  298
_refine_ls_R_factor_obs  0.025
_refine_ls_wR_factor_obs  0.036
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
  Br 0.90568(5) 0 -0.08162(3) 0.06900(10)
  Uani ?
  O1 0.4514(3) 0.20520(10)
  0.8484(3) 0.0587(7) Uani ?
  O2 0.3563(3) 0.33020(10)
  0.8239(3) 0.0667(8) Uani ?
  N1 0.9996(3) 0.28670(10)
  0.1697(3) 0.0526(8) Uani ?
  N2 0.4624(3) 0.27160(10)
  0.7739(3) 0.0440(7) Uani ?
  C1 1.1036(4) 0.2110(2) 0.1862(3) 0.0503(9) Uani ?
  C2 1.0321(3) 0.16870(10)
  0.3368(3) 0.0419(8) Uani ?
  C3 0.8738(3) 0.22160(10)
  0.4209(3) 0.0363(7) Uani ?
  C4 0.8579(4) 0.29550(10)
  0.3119(3) 0.0423(8) Uani ?
  C5 0.7132(4) 0.36030(10)
  0.3534(4) 0.0476(9) Uani ?
  C6 0.5876(4) 0.35220(10)
  0.5092(4) 0.0451(9) Uani ?
  C7 0.6063(3) 0.27950(10)
  0.6173(3) 0.0376(8) Uani ?
  C8 0.7450(3) 0.21450(10)
  0.5767(3) 0.0369(7) Uani ?
  C9 1.1022(4) 0.08380(10)
  0.3995(3) 0.0459(9) Uani ?
  C10 0.8616(4) 0.02730(10)
  0.3380(3) 0.0452(8) Uani ?
  C11 0.6999(4) 0.03110(10)
  0.1093(3) 0.0466(9) Uani ?
  H1N 1.026(6) 0.318(2) 0.070(4) 0.060(8) Uiso ?
  H1 1.230(6) 0.196(2) 0.107(4) 0.059(8) Uiso ?
  H5 0.729(8) 0.413(3) 0.277(6) 0.12(2) Uiso ?
  H6 0.493(5) 0.396(2) 0.542(4) 0.049(6) Uiso ?
  H8 0.738(5) 0.1660(10)
  0.637(4) 0.042(6) Uiso ?
  H9a 1.187(5) 0.080(2) 0.569(4) 0.056(7) Uiso ?
  H9b 1.245(5) 0.062(2) 0.326(4) 0.048(6) Uiso ?
  H10a 0.746(5) 0.040(2) 0.428(4) 0.062(8) Uiso ?
  H10b 0.918(5) -0.032(2) 0.384(4) 0.059(8) Uiso ?
  H11a 0.551(4) 0.005(3) 0.083(3) 0.052(7) Uiso ?
  H11b 0.655(5) 0.085(2) 0.069(4) 0.051(7) Uiso ?
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
  Br 0.08990(10)
  0.06530(10)
  0.05580(10)
  -0.00620(10)
  0.03660(9) -0.01280(10)
  O1 0.0612(6) 0.0578(9) 0.0572(7) 0.0040(7) 0.0331(6) 0.0076(8)
  O2 0.0723(7) 0.0603(9) 0.0683(9) 0.0171(7) 0.0348(6) -0.0065(9)
  N1 0.0551(7) 0.0580(10)
  0.0454(8) -0.0157(7) 0.0244(6) 0.0057(8)
  N2 0.0422(6) 0.0507(8) 0.0397(7) 0.0015(6) 0.0157(6) -0.0045(8)
  C1 0.0420(7) 0.0650(10)
  0.0464(8) -0.0142(8) 0.0227(6) -0.0080(10)
  C2 0.0343(6) 0.0520(10)
  0.0412(8) -0.0070(7) 0.0154(6) -0.0068(8)
  C3 0.0324(6) 0.0393(9) 0.0377(8) -0.0059(6) 0.0082(6) -0.0018(7)
  C4 0.0431(7) 0.0463(9) 0.0380(8) -0.0111(7) 0.0117(7) 0.0006(8)
  C5 0.0549(9) 0.0384(9) 0.0510(10)
  -0.0079(8) 0.0110(8) 0.0039(9)
  C6 0.0490(8) 0.0382(9) 0.0490(10)
  0.0001(8) 0.0133(7) -0.0015(9)
  C7 0.0377(7) 0.0410(9) 0.0344(7) -0.0007(6) 0.0084(6) -0.0009(8)
  C8 0.0369(6) 0.0384(8) 0.0354(7) -0.0031(7) 0.0117(6) -0.0012(8)
  C9 0.0378(7) 0.0530(10)
  0.0480(10)
  0.0059(8) 0.0131(7) -0.0058(9)
  C10 0.0496(7) 0.0437(9) 0.0425(8) 0.0039(7) 0.0228(6) 0.0011(8)
  C11 0.0459(7) 0.0438(9) 0.0500(10)
  0.0002(8) 0.0171(7) -0.0031(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  Br C11 1.955(2) yes
  O1 N2 1.227(3) yes
  O2 N2 1.220(3) yes
  N1 C1 1.373(3) yes
  N1 C4 1.365(3) yes
  N1 H1N 0.88(3) ?
  N2 C7 1.454(3) ?
  C1 C2 1.361(3) yes
  C1 H1 0.99(3) ?
  C2 C3 1.432(3) ?
  C2 C9 1.498(3) ?
  C3 C4 1.424(3) ?
  C3 C8 1.391(3) ?
  C4 C5 1.396(3) ?
  C5 C6 1.382(4) ?
  C5 H5 1.03(4) ?
  C6 C7 1.402(3) ?
  C6 H6 0.95(3) ?
  C7 C8 1.377(3) ?
  C8 H8 0.92(3) ?
  C9 C10 1.533(3) ?
  C9 H9a 1.08(2) ?
  C9 H9b 1.07(3) ?
  C10 C11 1.503(3) ?
  C10 H10a 0.99(3) ?
  C10 H10b 1.05(3) ?
  C11 H11a 0.86(3) ?
  C11 H11b 0.95(3) ?