data_2014730
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o10
_journal_page_last  o14
_publ_section_title
;
Hydrogen-bonded sheets in (E)-2-nitrobenzaldehyde 4-nitrophenylhydrazone
and a hydrogen-bonded framework structure in (E)-4-nitrobenzaldehyde
4-nitrophenylhydrazone
;
loop_
_publ_author_name
  'Wardell, James L.'
  'Skakle, Janet M. S.'
  'Low, John N.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C13 H10 N4 O4'
_chemical_formula_sum  'C13 H10 N4 O4'
_chemical_formula_iupac  'C13 H10 N4 O4'
_chemical_formula_weight  286.25
_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  5.9635(2)
_cell_length_b  11.0881(6)
_cell_length_c  18.9959(10)
_cell_angle_alpha  90.00
_cell_angle_beta  93.048(3)
_cell_angle_gamma  90.00
_cell_volume  1254.31(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.516
_diffrn_ambient_temperature  120(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
  O41 -0.1212(3) 0.13404(14) 0.65400(8) 0.0420(4) Uani d . 1 A . O
  O42 -0.3890(2) 0.05970(13) 0.58632(8) 0.0391(4) Uani d . 1 A . O
  O43 1.4174(3) 0.64695(14) 0.39835(8) 0.0421(4) Uani d . 1 A . O
  O44 1.4417(3) 0.64713(14) 0.28551(9) 0.0442(4) Uani d . 1 A . O
  N1A 0.2632(7) 0.2408(6) 0.36073(11) 0.025(2) Uiso d PD 0.50 A -1 N
  N1B 0.5531(6) 0.3516(5) 0.31090(10) 0.030(2) Uiso d PD 0.50 A -2 N
  N2 0.4504(2) 0.31008(14) 0.36808(8) 0.0291(4) Uani d D 1 . . N
  N4 -0.2078(3) 0.11089(16) 0.59496(9) 0.0307(4) Uani d . 1 . . N
  N14 1.3438(3) 0.61957(16) 0.33878(10) 0.0342(4) Uani d . 1 . . N
  C1 0.1473(3) 0.21167(17) 0.41867(9) 0.0255(4) Uani d D 1 . . C
  C2 -0.0598(3) 0.15298(17) 0.40960(10) 0.0283(5) Uani d . 1 A . C
  C3 -0.1778(3) 0.12053(18) 0.46694(10) 0.0283(5) Uani d . 1 . . C
  C4 -0.0871(3) 0.14613(17) 0.53388(10) 0.0263(4) Uani d . 1 A . C
  C5 0.1190(3) 0.20298(18) 0.54439(10) 0.0274(5) Uani d . 1 . . C
  C6 0.2356(3) 0.23594(17) 0.48690(10) 0.0277(5) Uani d . 1 A . C
  C11 0.7507(3) 0.41418(17) 0.31916(10) 0.0284(5) Uani d D 1 . . C
  C12 0.8686(4) 0.44211(19) 0.25952(11) 0.0315(5) Uani d . 1 A . C
  C13 1.0610(4) 0.51082(19) 0.26539(11) 0.0318(5) Uani d . 1 . . C
  C14 1.1371(3) 0.55071(18) 0.33158(10) 0.0283(5) Uani d . 1 A . C
  C15 1.0242(4) 0.52424(19) 0.39139(11) 0.0312(5) Uani d . 1 . . C
  C16 0.8309(4) 0.45679(19) 0.38504(11) 0.0305(5) Uani d . 1 A . C
  C17A 0.5557(7) 0.3334(6) 0.31248(11) 0.026(2) Uiso d PD 0.50 A -1 C
  C17B 0.2637(9) 0.2539(8) 0.35716(10) 0.031(3) Uiso d PD 0.50 A -2 C
  H1A 0.2118 0.2203 0.3181 0.030 Uiso d PR 0.50 A -1 H
  H1B 0.5003 0.3296 0.2687 0.036 Uiso d PR 0.50 A -2 H
  H2 -0.1196 0.1354 0.3634 0.034 Uiso calc R 1 . . H
  H3 -0.3190 0.0813 0.4607 0.034 Uiso calc R 1 A . H
  H5 0.1790 0.2190 0.5908 0.033 Uiso calc R 1 A . H
  H6 0.3766 0.2753 0.4935 0.033 Uiso calc R 1 . . H
  H12 0.8154 0.4134 0.2146 0.038 Uiso calc R 1 . . H
  H13 1.1401 0.5305 0.2248 0.038 Uiso calc R 1 A . H
  H15 1.0794 0.5523 0.4363 0.037 Uiso calc R 1 A . H
  H16 0.7512 0.4390 0.4258 0.037 Uiso calc R 1 . . H
  H17A 0.5088 0.2994 0.2682 0.031 Uiso calc PR 0.50 A -1 H
  H17B 0.2027 0.2400 0.3107 0.037 Uiso calc PR 0.50 A -2 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
  O41 0.0388(9) 0.0602(11) 0.0268(8) -0.0025(8) -0.0002(7) 0.0072(7)
  O42 0.0308(9) 0.0413(9) 0.0453(9) -0.0052(7) 0.0044(7) 0.0029(7)
  O43 0.0377(9) 0.0449(10) 0.0425(10) -0.0012(7) -0.0081(7) -0.0103(7)
  O44 0.0381(9) 0.0490(10) 0.0457(10) -0.0076(7) 0.0062(8) -0.0017(8)
  N2 0.0280(9) 0.0327(10) 0.0264(9) 0.0043(7) 0.0005(7) 0.0024(7)
  N4 0.0285(10) 0.0332(10) 0.0303(10) 0.0031(8) 0.0021(8) 0.0032(8)
  N14 0.0313(10) 0.0332(10) 0.0378(11) 0.0027(8) -0.0009(9) -0.0051(8)
  C1 0.0247(11) 0.0262(10) 0.0254(11) 0.0054(8) -0.0014(8) 0.0001(8)
  C2 0.0312(11) 0.0272(11) 0.0259(11) 0.0038(8) -0.0052(8) -0.0020(8)
  C3 0.0258(11) 0.0259(10) 0.0330(11) 0.0015(8) -0.0020(9) 0.0001(9)
  C4 0.0263(11) 0.0242(10) 0.0286(11) 0.0055(8) 0.0023(8) 0.0032(8)
  C5 0.0276(11) 0.0296(11) 0.0246(11) 0.0038(8) -0.0035(8) -0.0024(8)
  C6 0.0239(11) 0.0310(11) 0.0278(11) 0.0012(8) -0.0012(8) -0.0013(9)
  C11 0.0267(11) 0.0322(11) 0.0259(11) 0.0053(8) -0.0014(8) -0.0002(9)
  C12 0.0316(12) 0.0392(12) 0.0234(11) 0.0009(9) -0.0006(9) -0.0046(9)
  C13 0.0319(12) 0.0354(12) 0.0281(12) 0.0016(9) 0.0027(9) -0.0017(9)
  C14 0.0258(11) 0.0283(11) 0.0306(11) 0.0032(8) -0.0012(9) -0.0046(9)
  C15 0.0333(12) 0.0312(11) 0.0285(11) 0.0063(9) -0.0028(9) -0.0051(9)
  C16 0.0322(12) 0.0358(12) 0.0237(11) 0.0062(9) 0.0021(8) -0.0019(9)
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
  C1 C2 . 1.399(3) y
  C2 C3 . 1.376(3) y
  C3 C4 . 1.385(3) y
  C4 C5 . 1.386(3) y
  C5 C6 . 1.375(3) y
  C6 C1 . 1.399(3) y
  C4 N4 . 1.451(3) y
  N4 O41 . 1.236(2) y
  N4 O42 . 1.224(2) y
  C1 N1A . 1.3690(10) y
  N1A N2 . 1.3561(10) y
  N2 C17A . 1.2835(10) y
  C17A C11 . 1.4678(10) y
  C11 C12 . 1.400(3) y
  C12 C13 . 1.377(3) y
  C13 C14 . 1.386(3) y
  C14 C15 . 1.383(3) y
  C15 C16 . 1.374(3) y
  C16 C11 . 1.398(3) y
  C14 N14 . 1.450(3) y
  N14 O43 . 1.230(2) y
  N14 O44 . 1.233(2) y
  C1 C17B . 1.4670(10) y
  C17B N2 . 1.2831(10) y
  N2 N1B . 1.3557(10) y
  N1B C11 . 1.3690(10) y
  C2 H2 . 0.95 no
  C3 H3 . 0.95 no
  C5 H5 . 0.95 no
  C6 H6 . 0.95 no
  C12 H12 . 0.95 no
  C13 H13 . 0.95 no
  C15 H15 . 0.95 no
  C16 H16 . 0.95 no
  N1A H1A . 0.88 no
  N1B H1B . 0.8794 no
  C17A H17A . 0.95 no
  C17B H17B . 0.95 no