data_2013303
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o263
_journal_page_last  o267
_publ_section_title
;
Five (1H-pyrrol-2-yl)pyridines
;
loop_
_publ_author_name
  'Noland, Wayland E.'
  'Cole, Kevin P.'
  'Britton, Doyle'
_chemical_formula_moiety  'C9 H8 N2'
_chemical_formula_sum  'C9 H8 N2'
_chemical_formula_iupac  'C9 H8 N2'
_chemical_formula_weight  144.17
_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  5.3537(13)
_cell_length_b  11.654(3)
_cell_length_c  11.990(3)
_cell_angle_alpha  90.00
_cell_angle_beta  98.100(10)
_cell_angle_gamma  90.00
_cell_volume  740.6(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  174(2)
_exptl_crystal_density_diffrn  1.293
_diffrn_ambient_temperature  174(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
  N1 0.1570(2) 0.18720(11) 0.49705(10) 0.0382(4) Uani d . 1 . . N
  C2 0.3451(3) 0.26068(13) 0.53070(12) 0.0353(4) Uani d . 1 . . C
  H2 0.4423 0.2876 0.4756 0.042 Uiso calc R 1 . . H
  C3 0.4083(2) 0.30048(12) 0.64082(11) 0.0288(3) Uani d . 1 . . C
  C4 0.2632(3) 0.25840(13) 0.72014(12) 0.0315(4) Uani d . 1 . . C
  H4 0.2980 0.2822 0.7965 0.038 Uiso calc R 1 . . H
  C5 0.0695(3) 0.18224(13) 0.68719(12) 0.0343(4) Uani d . 1 . . C
  H5 -0.0298 0.1530 0.7405 0.041 Uiso calc R 1 . . H
  C6 0.0218(3) 0.14906(13) 0.57566(12) 0.0361(4) Uani d . 1 . . C
  H6 -0.1126 0.0970 0.5536 0.043 Uiso calc R 1 . . H
  C7 0.6152(3) 0.38164(12) 0.66867(11) 0.0296(3) Uani d . 1 . . C
  N8 0.7188(2) 0.40504(10) 0.77786(10) 0.0309(3) Uani d . 1 . . N
  H8 0.678(3) 0.3731(15) 0.8438(14) 0.044(5) Uiso d . 1 . . H
  C9 0.9103(3) 0.48217(13) 0.77801(13) 0.0352(4) Uani d . 1 . . C
  H9 1.0127 0.5115 0.8429 0.042 Uiso calc R 1 . . H
  C10 0.9299(3) 0.51011(14) 0.66894(13) 0.0381(4) Uani d . 1 . . C
  H10 1.0463 0.5627 0.6443 0.046 Uiso calc R 1 . . H
  C11 0.7455(3) 0.44653(13) 0.59991(13) 0.0354(4) Uani d . 1 . . C
  H11 0.7160 0.4480 0.5199 0.042 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
  N1 0.0423(7) 0.0413(8) 0.0305(7) -0.0014(6) 0.0027(5) -0.0030(6)
  C2 0.0404(8) 0.0382(8) 0.0278(8) -0.0003(7) 0.0071(6) 0.0006(6)
  C3 0.0313(7) 0.0268(7) 0.0279(7) 0.0065(6) 0.0030(5) 0.0023(6)
  C4 0.0349(7) 0.0333(8) 0.0262(7) 0.0041(6) 0.0041(6) -0.0017(6)
  C5 0.0346(8) 0.0368(8) 0.0321(8) -0.0001(7) 0.0075(6) 0.0016(6)
  C6 0.0348(7) 0.0355(8) 0.0373(8) -0.0011(7) 0.0026(6) -0.0027(7)
  C7 0.0326(7) 0.0300(7) 0.0263(7) 0.0058(6) 0.0047(6) 0.0005(6)
  N8 0.0348(6) 0.0325(7) 0.0257(7) 0.0014(5) 0.0057(5) -0.0004(5)
  C9 0.0326(8) 0.0349(8) 0.0384(9) -0.0001(7) 0.0056(6) -0.0055(6)
  C10 0.0372(8) 0.0359(8) 0.0429(9) -0.0017(7) 0.0120(7) 0.0002(7)
  C11 0.0394(8) 0.0370(8) 0.0306(8) 0.0023(7) 0.0077(6) 0.0013(6)
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
  N1 C2 . 1.340(2) ?
  N1 C6 . 1.342(2) ?
  C2 C3 . 1.395(2) ?
  C2 H2 . 0.9500 ?
  C3 C4 . 1.399(2) ?
  C3 C7 . 1.459(2) ?
  C4 C5 . 1.380(2) ?
  C4 H4 . 0.9500 ?
  C5 C6 . 1.381(2) ?
  C5 H5 . 0.9500 ?
  C6 H6 . 0.9500 ?
  C7 N8 . 1.375(2) ?
  C7 C11 . 1.379(2) ?
  N8 C9 . 1.364(2) ?
  N8 H8 . 0.93(2) ?
  C9 C10 . 1.366(2) ?
  C9 H9 . 0.9500 ?
  C10 C11 . 1.406(2) ?
  C10 H10 . 0.9500 ?
  C11 H11 . 0.9500 ?