#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013306.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_2013306
_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
;
_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
  '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
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  5.1519(13)
_cell_length_b  19.739(5)
_cell_length_c  14.694(4)
_cell_angle_alpha  90.00
_cell_angle_beta  95.260(10)
_cell_angle_gamma  90.00
_cell_volume  1488.0(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.287
_diffrn_ambient_temperature  173(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
  N1A 0.559(4) 0.3845(15) 0.3992(5) 0.046(3) Uani d PD 0.525(7) A 1 N
  C2A 0.4897(15) 0.4178(4) 0.4718(5) 0.0510(15) Uani d PD 0.525(7) A 1 C
  H2A 0.3639 0.4529 0.4618 0.061 Uiso calc PR 0.525(7) A 1 H
  C3A 0.5876(16) 0.4051(4) 0.5606(5) 0.0489(16) Uani d PD 0.525(7) A 1 C
  H3A 0.5355 0.4324 0.6089 0.059 Uiso calc PR 0.525(7) A 1 H
  C4A 0.763(6) 0.3520(19) 0.5797(7) 0.0395(15) Uani d PD 0.525(7) A 1 C
  C5A 0.832(2) 0.3153(6) 0.5038(10) 0.050(3) Uani d PD 0.525(7) A 1 C
  H5A 0.9520 0.2788 0.5119 0.060 Uiso calc PR 0.525(7) A 1 H
  C6A 0.725(3) 0.3324(9) 0.4178(8) 0.056(3) Uani d PD 0.525(7) A 1 C
  H6A 0.7710 0.3057 0.3679 0.067 Uiso calc PR 0.525(7) A 1 H
  N1A' 0.540(5) 0.3729(16) 0.3969(6) 0.046(3) Uani d PD 0.475(7) A 2 N
  C2A' 0.4238(17) 0.3930(4) 0.4694(6) 0.0510(15) Uani d PD 0.475(7) A 2 C
  H2A' 0.2637 0.4169 0.4588 0.061 Uiso calc PR 0.475(7) A 2 H
  C3A' 0.5191(18) 0.3817(5) 0.5589(6) 0.0489(16) Uani d PD 0.475(7) A 2 C
  H3A' 0.4237 0.3970 0.6073 0.059 Uiso calc PR 0.475(7) A 2 H
  C4A' 0.755(7) 0.348(2) 0.5784(8) 0.0395(15) Uani d PD 0.475(7) A 2 C
  C5A' 0.887(2) 0.3297(7) 0.5025(11) 0.050(3) Uani d PD 0.475(7) A 2 C
  H5A' 1.0513 0.3078 0.5110 0.060 Uiso calc PR 0.475(7) A 2 H
  C6A' 0.776(3) 0.3435(10) 0.4159(9) 0.056(3) Uani d PD 0.475(7) A 2 C
  H6A' 0.8709 0.3315 0.3660 0.067 Uiso calc PR 0.475(7) A 2 H
  C7A 0.8633(4) 0.33406(9) 0.67166(13) 0.0393(5) Uani d . 1 A 1 C
  N8A 0.7479(3) 0.35683(9) 0.74647(11) 0.0444(4) Uani d . 1 A 1 N
  H8A 0.612(4) 0.3867(11) 0.7484(13) 0.056(6) Uiso d . 1 B 1 H
  C9A 0.8816(4) 0.33289(11) 0.82370(14) 0.0512(6) Uani d . 1 A 1 C
  H9A 0.8412 0.3415 0.8844 0.061 Uiso calc R 1 A 1 H
  C10A 1.0844(4) 0.29430(11) 0.79918(14) 0.0536(6) Uani d . 1 A 1 C
  H10A 1.2097 0.2714 0.8395 0.064 Uiso calc R 1 A 1 H
  C11A 1.0730(4) 0.29477(10) 0.70346(14) 0.0484(5) Uani d . 1 A 1 C
  H11A 1.1891 0.2721 0.6671 0.058 Uiso calc R 1 A 1 H
  N1B 0.3322(3) 0.45933(8) 0.76455(11) 0.0455(4) Uani d . 1 C 1 N
  C2B 0.1425(4) 0.48763(10) 0.70906(14) 0.0465(5) Uani d . 1 C 1 C
  H2B 0.1323 0.4760 0.6461 0.056 Uiso calc R 1 C 1 H
  C3B -0.0396(4) 0.53260(10) 0.73675(13) 0.0440(5) Uani d . 1 C 1 C
  H3B -0.1703 0.5504 0.6934 0.053 Uiso calc R 1 C 1 H
  C4B -0.0322(3) 0.55191(9) 0.82781(12) 0.0372(5) Uani d . 1 C 1 C
  C5B 0.1636(4) 0.52192(10) 0.88640(13) 0.0446(5) Uani d . 1 C 1 C
  H5B 0.1777 0.5322 0.9498 0.054 Uiso calc R 1 C 1 H
  C6B 0.3359(4) 0.47750(10) 0.85222(14) 0.0465(5) Uani d . 1 C 1 C
  H6B 0.4673 0.4583 0.8940 0.056 Uiso calc R 1 C 1 H
  C7B -0.2144(4) 0.60047(9) 0.86040(12) 0.0381(5) Uani d . 1 C 1 C
  N8B -0.4080(3) 0.63014(8) 0.80317(11) 0.0402(4) Uani d . 1 C 1 N
  H8B -0.447(4) 0.6232(9) 0.7393(13) 0.049(6) Uiso d . 1 D 1 H
  C9B -0.5502(4) 0.67238(10) 0.85214(14) 0.0465(5) Uani d . 1 C 1 C
  H9B -0.6957 0.6985 0.8284 0.056 Uiso calc R 1 C 1 H
  C10B -0.4484(4) 0.67091(11) 0.94137(15) 0.0529(6) Uani d . 1 C 1 C
  H10B -0.5093 0.6958 0.9905 0.063 Uiso calc R 1 C 1 H
  C11B -0.2371(4) 0.62571(10) 0.94692(13) 0.0477(5) Uani d . 1 C 1 C
  H11B -0.1289 0.6145 1.0007 0.057 Uiso calc R 1 C 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
  N1A 0.054(3) 0.036(8) 0.0480(11) -0.003(5) 0.0045(10) -0.0035(13)
  C2A 0.051(3) 0.048(4) 0.0532(16) 0.009(3) 0.003(2) 0.000(3)
  C3A 0.047(4) 0.053(5) 0.0469(14) 0.010(3) 0.003(2) -0.003(3)
  C4A 0.0388(17) 0.030(3) 0.0497(12) -0.005(2) 0.0030(10) -0.0004(11)
  C5A 0.053(4) 0.042(5) 0.0563(16) 0.009(4) 0.006(3) -0.003(3)
  C6A 0.065(5) 0.050(5) 0.0518(15) 0.010(5) 0.009(2) -0.006(2)
  N1A' 0.054(3) 0.036(8) 0.0480(11) -0.003(5) 0.0045(10) -0.0035(13)
  C2A' 0.051(3) 0.048(4) 0.0532(16) 0.009(3) 0.003(2) 0.000(3)
  C3A' 0.047(4) 0.053(5) 0.0469(14) 0.010(3) 0.003(2) -0.003(3)
  C4A' 0.0388(17) 0.030(3) 0.0497(12) -0.005(2) 0.0030(10) -0.0004(11)
  C5A' 0.053(4) 0.042(5) 0.0563(16) 0.009(4) 0.006(3) -0.003(3)
  C6A' 0.065(5) 0.050(5) 0.0518(15) 0.010(5) 0.009(2) -0.006(2)
  C7A 0.0388(11) 0.0318(11) 0.0471(12) -0.0019(9) 0.0026(9) -0.0013(9)
  N8A 0.0437(10) 0.0438(11) 0.0453(10) 0.0009(9) 0.0024(8) 0.0032(8)
  C9A 0.0501(13) 0.0549(14) 0.0475(13) -0.0066(11) -0.0016(10) 0.0082(10)
  C10A 0.0484(13) 0.0487(13) 0.0613(15) -0.0026(11) -0.0087(11) 0.0132(11)
  C11A 0.0441(12) 0.0384(12) 0.0620(14) 0.0026(10) 0.0017(10) 0.0021(10)
  N1B 0.0419(10) 0.0415(10) 0.0533(11) -0.0023(8) 0.0047(8) 0.0028(8)
  C2B 0.0476(12) 0.0453(13) 0.0467(12) -0.0022(11) 0.0045(10) -0.0039(10)
  C3B 0.0415(12) 0.0464(12) 0.0440(12) 0.0032(10) 0.0022(9) -0.0003(9)
  C4B 0.0353(11) 0.0347(11) 0.0417(11) -0.0077(9) 0.0040(9) 0.0011(8)
  C5B 0.0451(12) 0.0462(13) 0.0425(12) -0.0027(10) 0.0043(9) 0.0025(9)
  C6B 0.0416(12) 0.0475(13) 0.0501(13) -0.0014(10) 0.0024(10) 0.0073(10)
  C7B 0.0366(11) 0.0354(11) 0.0422(11) -0.0068(9) 0.0029(9) -0.0006(9)
  N8B 0.0410(10) 0.0362(10) 0.0437(10) -0.0023(8) 0.0054(8) -0.0021(8)
  C9B 0.0464(12) 0.0380(12) 0.0566(14) 0.0017(10) 0.0123(10) -0.0016(10)
  C10B 0.0584(14) 0.0446(13) 0.0579(14) -0.0054(11) 0.0176(11) -0.0096(11)
  C11B 0.0504(13) 0.0487(13) 0.0441(12) -0.0085(11) 0.0050(10) -0.0023(10)
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
  N1A C2A . 1.331(6) ?
  N1A C6A . 1.349(9) ?
  C2A C3A . 1.378(3) ?
  C2A H2A . 0.9500 ?
  C3A C4A . 1.394(9) ?
  C3A H3A . 0.9500 ?
  C4A C5A . 1.403(9) ?
  C4A C7A . 1.447(9) ?
  C5A C6A . 1.374(3) ?
  C5A H5A . 0.9500 ?
  C6A H6A . 0.9500 ?
  N1A' C2A' . 1.331(5) ?
  N1A' C6A' . 1.349(10) ?
  C2A' C3A' . 1.378(3) ?
  C2A' H2A' . 0.9500 ?
  C3A' C4A' . 1.394(9) ?
  C3A' H3A' . 0.9500 ?
  C4A' C5A' . 1.403(9) ?
  C5A' C6A' . 1.374(3) ?
  C5A' H5A' . 0.9500 ?
  C6A' H6A' . 0.9500 ?
  C7A N8A . 1.372(2) ?
  C7A C11A . 1.377(3) ?
  N8A C9A . 1.357(2) ?
  N8A H8A . 0.92(2) ?
  C9A C10A . 1.368(3) ?
  C9A H9A . 0.9500 ?
  C10A C11A . 1.402(3) ?
  C10A H10A . 0.9500 ?
  C11A H11A . 0.9500 ?
  N1B C6B . 1.336(2) ?
  N1B C2B . 1.336(2) ?
  C2B C3B . 1.380(3) ?
  C2B H2B . 0.9500 ?
  C3B C4B . 1.388(2) ?
  C3B H3B . 0.9500 ?
  C4B C5B . 1.396(3) ?
  C4B C7B . 1.453(3) ?
  C5B C6B . 1.375(3) ?
  C5B H5B . 0.9500 ?
  C6B H6B . 0.9500 ?
  C7B N8B . 1.375(2) ?
  C7B C11B . 1.380(3) ?
  N8B C9B . 1.358(2) ?
  N8B H8B . 0.952(19) ?
  C9B C10B . 1.367(3) ?
  C9B H9B . 0.9500 ?
  C10B C11B . 1.404(3) ?
  C10B H10B . 0.9500 ?
  C11B H11B . 0.9500 ?
_cod_database_code 2013306