data_2202147
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o342
_journal_page_last  o343
_publ_section_title
;
Salicylaldehyde 4-nitrophenylhydrazone
;
loop_
_publ_author_name
  'Shang Shan'
  'Duan-Jun Xu'
  'Jing-Yun Wu'
  'Michael Y. Chiang'
_chemical_formula_moiety  'C13 H11 N3 O3'
_chemical_formula_sum  'C13 H11 N3 O3'
_chemical_formula_iupac  'C13 H11 N3 O3'
_chemical_formula_weight  257.25
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P c'
_symmetry_space_group_name_Hall  'P -2yc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y, z+1/2'
_cell_length_a  5.0052(11)
_cell_length_b  9.9004(16)
_cell_length_c  12.1749(12)
_cell_angle_alpha  90.00
_cell_angle_beta  92.199(15)
_cell_angle_gamma  90.00
_cell_volume  602.86(17)
_cell_formula_units_Z  2
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.417
_diffrn_ambient_temperature  298(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 1.1219(6) 0.0500(3) 0.5900(2) 0.0774(8) Uani d . 1 . . O
  O2 1.1702(6) -0.1120(3) 0.4758(3) 0.0880(10) Uani d . 1 . . O
  O3 -0.0249(5) 0.5120(2) 0.3978(2) 0.0635(7) Uani d . 1 . . O
  N1 1.0663(6) -0.0053(3) 0.5016(3) 0.0576(8) Uani d . 1 . . N
  N2 0.2966(5) 0.2283(3) 0.2189(2) 0.0479(7) Uani d . 1 . . N
  H1 0.2781 0.1981 0.1528 0.057 Uiso calc R 1 . . H
  N3 0.1378(5) 0.3308(2) 0.2531(2) 0.0446(6) Uani d . 1 . . N
  C1 0.4849(6) 0.1739(3) 0.2897(3) 0.0417(7) Uani d . 1 . . C
  C2 0.6294(7) 0.0607(3) 0.2557(3) 0.0515(8) Uani d . 1 . . C
  H2 0.5952 0.0251 0.1859 0.062 Uiso calc R 1 . . H
  C3 0.8191(6) 0.0024(3) 0.3237(3) 0.0529(9) Uani d . 1 . . C
  H3 0.9124 -0.0730 0.3006 0.063 Uiso calc R 1 . . H
  C4 0.8723(7) 0.0565(3) 0.4277(3) 0.0454(7) Uani d . 1 . . C
  C5 0.7345(6) 0.1688(4) 0.4615(3) 0.0509(8) Uani d . 1 . . C
  H5 0.7724 0.2051 0.5308 0.061 Uiso calc R 1 . . H
  C6 0.5424(6) 0.2272(3) 0.3939(3) 0.0481(8) Uani d . 1 . . C
  H6 0.4500 0.3027 0.4176 0.058 Uiso calc R 1 . . H
  C7 -0.0384(6) 0.3772(3) 0.1848(3) 0.0475(8) Uani d . 1 . . C
  H7 -0.0531 0.3402 0.1146 0.057 Uiso calc R 1 . . H
  C8 -0.2189(6) 0.4873(3) 0.2140(3) 0.0464(8) Uani d . 1 . . C
  C9 -0.2040(6) 0.5500(3) 0.3169(3) 0.0505(8) Uani d . 1 . . C
  C10 -0.3793(8) 0.6534(4) 0.3392(4) 0.0656(11) Uani d . 1 . . C
  H10 -0.3685 0.6961 0.4072 0.079 Uiso calc R 1 . . H
  C11 -0.5690(7) 0.6935(4) 0.2618(4) 0.0690(11) Uani d . 1 . . C
  H11 -0.6864 0.7627 0.2784 0.083 Uiso calc R 1 . . H
  C12 -0.5887(7) 0.6337(4) 0.1604(3) 0.0619(10) Uani d . 1 . . C
  H12 -0.7185 0.6617 0.1086 0.074 Uiso calc R 1 . . H
  C13 -0.4131(7) 0.5312(3) 0.1361(3) 0.0555(9) Uani d . 1 . . C
  H13 -0.4241 0.4908 0.0672 0.067 Uiso calc R 1 . . H
  H9 0.0943 0.4491 0.3658 0.080 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 0.0806(18) 0.100(2) 0.0505(15) 0.0174(17) -0.0127(13) 0.0054(15)
  O2 0.097(2) 0.0724(18) 0.093(2) 0.0349(18) -0.0158(17) -0.0003(16)
  O3 0.0676(15) 0.0649(14) 0.0577(13) 0.0085(14) -0.0021(12) -0.0073(13)
  N1 0.0542(18) 0.0573(19) 0.0612(19) 0.0059(16) 0.0000(16) 0.0135(16)
  N2 0.0473(14) 0.0471(16) 0.0486(16) 0.0079(14) -0.0065(13) -0.0080(13)
  N3 0.0436(13) 0.0392(14) 0.0509(14) 0.0009(13) 0.0011(12) 0.0017(12)
  C1 0.0376(16) 0.0391(16) 0.0485(17) -0.0040(14) 0.0041(14) -0.0024(14)
  C2 0.0492(18) 0.0512(18) 0.054(2) 0.0034(18) -0.0056(15) -0.0148(17)
  C3 0.0493(19) 0.0416(17) 0.068(2) 0.0077(16) -0.0002(18) -0.0060(16)
  C4 0.0427(16) 0.0443(17) 0.0493(17) 0.0020(15) 0.0016(13) 0.0075(16)
  C5 0.056(2) 0.053(2) 0.0436(18) 0.0015(17) -0.0015(16) -0.0027(16)
  C6 0.0518(19) 0.0449(17) 0.0473(19) 0.0035(16) -0.0005(16) -0.0034(16)
  C7 0.0455(17) 0.0481(18) 0.0491(18) -0.0008(17) 0.0037(16) 0.0010(16)
  C8 0.0416(16) 0.0447(18) 0.0535(18) 0.0000(14) 0.0092(15) 0.0102(15)
  C9 0.052(2) 0.0454(19) 0.054(2) -0.0012(17) 0.0081(17) 0.0060(17)
  C10 0.073(3) 0.0493(19) 0.075(2) 0.006(2) 0.016(2) -0.0067(19)
  C11 0.063(2) 0.056(2) 0.090(3) 0.020(2) 0.025(2) 0.015(2)
  C12 0.051(2) 0.063(2) 0.072(2) 0.0120(19) 0.0103(18) 0.027(2)
  C13 0.053(2) 0.057(2) 0.056(2) 0.0059(19) 0.0060(17) 0.0123(18)
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 N1 . 1.229(4) yes
  O2 N1 . 1.224(4) yes
  O3 C9 . 1.359(4) yes
  O3 H9 . 0.956 ?
  N1 C4 . 1.436(4) yes
  N2 C1 . 1.364(4) yes
  N2 N3 . 1.364(3) yes
  N2 H1 . 0.860 ?
  N3 C7 . 1.274(4) yes
  C1 C6 . 1.394(4) ?
  C1 C2 . 1.404(5) ?
  C2 C3 . 1.364(5) ?
  C2 H2 . 0.930 ?
  C3 C4 . 1.391(5) ?
  C3 H3 . 0.930 ?
  C4 C5 . 1.379(5) ?
  C5 C6 . 1.370(5) ?
  C5 H5 . 0.930 ?
  C6 H6 . 0.930 ?
  C7 C8 . 1.468(4) yes
  C7 H7 . 0.930 ?
  C8 C9 . 1.398(4) ?
  C8 C13 . 1.401(5) ?
  C9 C10 . 1.382(5) ?
  C10 C11 . 1.371(5) ?
  C10 H10 . 0.930 ?
  C11 C12 . 1.368(6) ?
  C11 H11 . 0.930 ?
  C12 C13 . 1.382(5) ?
  C12 H12 . 0.930 ?
  C13 H13 . 0.930 ?