data_2200308
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o411
_journal_page_last  o413
_publ_section_title
;
4-[(3-Pyridylamino)methyl]phenol
;
loop_
_publ_author_name
  'Chen, Zhen-Feng'
  'Xie, Yong-Rong'
  'Fun, Hoong-Kun'
  'Chantrapromma, Suchada'
  'Razak, Ibrahim Abdul'
  'Xiong, Ren-Gen'
  'You, Xiao-Zeng'
_chemical_formula_moiety  'C12 H12 N2 O'
_chemical_formula_sum  'C12 H12 N2 O'
_chemical_formula_iupac  'C12 H12 N2 O'
_chemical_formula_weight  200.24
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  6.5392(2)
_cell_length_b  7.60770(10)
_cell_length_c  20.3127(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1010.52(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.316
_diffrn_ambient_temperature  293(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
  O1  -.1374(3)  -.2800(3)  .13307(10)  .0513(6) Uani d . 1 . . O
  N1  .4632(4)  -.0819(3)  .36769(12)  .0474(7) Uani d . 1 . . N
  N2  .6644(4)  .0710(3)  .52458(11)  .0565(7) Uani d . 1 . . N
  C1  .1771(4)  -.2875(4)  .28009(14)  .0429(7) Uani d . 1 . . C
  H1C  .1673  -.3289  .3230  .051 Uiso calc R 1 . . H
  C2  .0173(5)  -.3155(4)  .23731(13)  .0423(7) Uani d . 1 . . C
  H2B  -.0978  -.3767  .2515  .051 Uiso calc R 1 . . H
  C3  .0265(4)  -.2536(3)  .17339(12)  .0382(7) Uani d . 1 . . C
  C4  .2022(4)  -.1703(4)  .15207(13)  .0434(7) Uani d . 1 . . C
  H4A  .2124  -.1317  .1088  .052 Uiso calc R 1 . . H
  C5  .3637(5)  -.1444(3)  .19547(13)  .0423(7) Uani d . 1 . . C
  H5A  .4819  -.0895  .1805  .051 Uiso calc R 1 . . H
  C6  .3529(4)  -.1985(3)  .26062(12)  .0378(7) Uani d . 1 . . C
  C7  .5280(5)  -.1666(4)  .30710(13)  .0449(7) Uani d . 1 . . C
  H7A  .5924  -.2780  .3176  .054 Uiso calc R 1 . . H
  H7B  .6291  -.0933  .2855  .054 Uiso calc R 1 . . H
  C8  .5991(4)  -.0572(3)  .41807(12)  .0387(6) Uani d . 1 . . C
  C9  .5452(5)  .0443(4)  .47296(13)  .0489(8) Uani d . 1 . . C
  H9A  .4166  .0965  .4731  .059 Uiso calc R 1 . . H
  C10  .8513(6)  -.0047(5)  .52411(16)  .0633(9) Uani d . 1 . . C
  H10A  .9368  .0117  .5602  .076 Uiso calc R 1 . . H
  C11  .9195(5)  -.1041(4)  .47280(15)  .0547(8) Uani d . 1 . . C
  H11A 1.0489  -.1546  .4742  .066 Uiso calc R 1 . . H
  C12  .7959(4)  -.1290(4)  .41932(14)  .0472(8) Uani d . 1 . . C
  H12A  .8430  -.1939  .3836  .057 Uiso calc R 1 . . H
  H1A  -.132(6)  -.209(5)  .0927(18)  .099(13) Uiso d . 1 . . H
  H1B  .364(5)  -.004(4)  .3607(16)  .077(11) Uiso d . 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
  O1  .0491(12)  .0528(13)  .0519(12)  -.0139(10)  -.0053(11)  .0062(10)
  N1  .0466(15)  .0442(14)  .0514(14)  .0119(13)  -.0039(13)  -.0065(12)
  N2  .0592(17)  .0591(17)  .0512(15)  -.0067(14)  -.0055(15)  -.0101(13)
  C1  .0475(18)  .0395(17)  .0417(14)  -.0016(14)  .0079(15)  .0052(12)
  C2  .0416(16)  .0336(14)  .0518(18)  -.0043(13)  .0103(15)  .0045(13)
  C3  .0416(17)  .0311(14)  .0420(15)  -.0008(13)  .0041(14)  -.0034(12)
  C4  .0516(18)  .0425(16)  .0362(14)  -.0050(14)  .0119(15)  -.0013(12)
  C5  .0399(16)  .0379(15)  .0490(17)  -.0068(13)  .0112(15)  -.0048(13)
  C6  .0392(16)  .0315(15)  .0429(16)  .0062(13)  .0069(14)  -.0026(12)
  C7  .0433(17)  .0412(16)  .0501(17)  .0026(14)  .0006(15)  -.0030(13)
  C8  .0415(15)  .0315(14)  .0431(15)  -.0012(12)  -.0048(14)  .0034(13)
  C9  .0507(18)  .0430(17)  .0530(17)  .0017(15)  -.0030(17)  -.0029(14)
  C10  .060(2)  .070(2)  .060(2)  -.007(2)  -.017(2)  -.0010(17)
  C11  .0487(19)  .056(2)  .0591(19)  .0044(15)  -.0121(17)  .0053(16)
  C12  .0470(18)  .0414(17)  .0532(17)  .0042(15)  .0014(16)  .0022(14)
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 C3 . 1.363(3) yes
  O1 H1A .  .98(4) ?
  N1 C8 . 1.368(3) yes
  N1 C7 . 1.453(3) yes
  N1 H1B .  .89(3) ?
  N2 C9 . 1.322(3) yes
  N2 C10 . 1.351(4) yes
  C1 C2 . 1.376(4) ?
  C1 C6 . 1.392(4) ?
  C1 H1C .  .9300 ?
  C2 C3 . 1.383(4) ?
  C2 H2B .  .9300 ?
  C3 C4 . 1.382(4) ?
  C4 C5 . 1.390(4) ?
  C4 H4A .  .9300 ?
  C5 C6 . 1.388(3) ?
  C5 H5A .  .9300 ?
  C6 C7 . 1.504(4) ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C8 C12 . 1.398(4) ?
  C8 C9 . 1.401(4) ?
  C9 H9A .  .9300 ?
  C10 C11 . 1.363(4) ?
  C10 H10A .  .9300 ?
  C11 C12 . 1.367(4) ?
  C11 H11A .  .9300 ?
  C12 H12A .  .9300 ?