Related literature   {#sec1}
====================

For the coordination chemistry of Schiff base and hydrazone compounds, see: Kucukguzel *et al.* (2006[@bb5]); Khattab *et al.* (2005[@bb4]); Karthikeyan *et al.* (2006[@bb3]). For a closely related 4-amino­benzohydrazide and its Schiff base structures and further background references, see: Xu (2012[@bb9]); Shi & Li (2012[@bb8]); Bakir & Green (2002[@bb1]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

C~14~H~12~N~4~O~3~*M* *~r~* = 284.28Monoclinic,*a* = 6.4594 (13) Å*b* = 4.5998 (13) Å*c* = 20.598 (5) Åβ = 95.08 (4)°*V* = 609.6 (3) Å^3^*Z* = 2Mo *K*α radiationμ = 0.11 mm^−1^*T* = 296 K0.25 × 0.18 × 0.10 mm

### Data collection   {#sec2.1.2}

Bruker SMART CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 1996[@bb6]) *T* ~min~ = 0.976, *T* ~max~ = 0.9894632 measured reflections2710 independent reflections1516 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.048

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.045*wR*(*F* ^2^) = 0.111*S* = 1.052710 reflections190 parametersH-atom parameters constrainedΔρ~max~ = 0.27 e Å^−3^Δρ~min~ = −0.22 e Å^−3^

 {#d5e471}

Data collection: *SMART* (Bruker, 2007[@bb2]); cell refinement: *SAINT* (Bruker, 2007[@bb2]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb7]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb7]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb7]); software used to prepare material for publication: *SHELXTL*.

Supplementary Material
======================

Crystal structure: contains datablock(s) global, I. DOI: [10.1107/S1600536812020855/tk5092sup1.cif](http://dx.doi.org/10.1107/S1600536812020855/tk5092sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812020855/tk5092Isup2.hkl](http://dx.doi.org/10.1107/S1600536812020855/tk5092Isup2.hkl)

Supplementary material file. DOI: [10.1107/S1600536812020855/tk5092Isup3.cml](http://dx.doi.org/10.1107/S1600536812020855/tk5092Isup3.cml)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?tk5092&file=tk5092sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?tk5092sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?tk5092&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [TK5092](http://scripts.iucr.org/cgi-bin/sendsup?tk5092)).

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 2011GXNSFB018023) and the Natural Science Foundation of the Education Bureau of Guangxi Province (grant No. 201106LX535). This work was also supported by the Program for Excellent Talents in Guangxi Higher Education Institutions and the Dean's project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (grant No. K011).

Comment
=======

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Karthikeyan *et al.*, 2006; Khattab, 2005; Kucukguzel *et al.*, 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide and closely related to the title compound have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002). In order to explore new anti-bacterial compounds, a new hydrazone derivative was prepared and characterized crystallographically.

As shown in Fig. 1, the asymmetric unit of the title compound, (I), contains one independent molecule displaying an *E* configuration with respect to its C═N double bond. The dihedral angle between the two benzene rings is 3.2 (5)°. The bond lengths and angles are as expected for a compound of this type and agree with the other ligands belonging to the hydrazone series. The C8═N3 and C7═O1 bond lengths of 1.268 (3) and 1.226 (3) Å, respectively, are the expected values for such double bonds. In the crystal packing, it is noted that amino-H (H1A, H1B) and amide-H2A atoms are involved in forming intermolecular N---H···O and N---H···N hydrogen bonds (Fig. 2 and Table 1), linking the molecules into a two-dimensional layer structure that stacks along the *c* axis. Weak C---H···O interactions are also noted within the layer.

Experimental {#experimental}
============

To a methanol solution (20 ml) of 2-nitrobenzaldehyde (1 mmol, 0.151 g) and 4-aminobenzohydrazide (1 mmol, 0.151 g), a few drops of acetic acid were added. The mixture was refluxed for 2 h and then cooled to room temperature to give a yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 6 days at room temperature.

Refinement {#refinement}
==========

H-atoms were placed in calculated positions (C---H = 0.93 and N---H = 0.86--0.89 Å) and were included in the refinement in the riding model approximation, with *U*~iso~(H) set to 1.2*U*~eq~(C or N). In the absence of significant anomalous scattering effects, 1120 Friedel pairs were averaged in the final refinement.

Figures
=======

![The molecular structure of the title compound, with displacement ellipsoids at the 30% probability level.](e-68-o1726-fig1){#Fap1}

![Crystal packing in the title compound where molecules are linked via N---H···O and N--H···N hydrogen bonds (dashed lines). Except for those involved in hydrogen-bonding interactions, H atoms have been omitted for clarity.](e-68-o1726-fig2){#Fap2}

Crystal data {#tablewrapcrystaldatalong}
============

  ---------------------- ---------------------------------------
  C~14~H~12~N~4~O~3~     *F*(000) = 296
  *M~r~* = 284.28        *D*~x~ = 1.549 Mg m^−3^
  Monoclinic, *P*2~1~    Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: P 2yb     Cell parameters from 7138 reflections
  *a* = 6.4594 (13) Å    θ = 1.4--27.5°
  *b* = 4.5998 (13) Å    µ = 0.11 mm^−1^
  *c* = 20.598 (5) Å     *T* = 296 K
  β = 95.08 (4)°         Block, yellow
  *V* = 609.6 (3) Å^3^   0.25 × 0.18 × 0.10 mm
  *Z* = 2                
  ---------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  --------------------------------------------------------------- --------------------------------------
  Bruker SMART CCD area-detector diffractometer                   2710 independent reflections
  Radiation source: fine-focus sealed tube                        1516 reflections with *I* \> 2σ(*I*)
  Graphite monochromator                                          *R*~int~ = 0.048
  φ and ω scans                                                   θ~max~ = 27.5°, θ~min~ = 2.0°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 1996)   *h* = −8→7
  *T*~min~ = 0.976, *T*~max~ = 0.989                              *k* = −6→5
  4632 measured reflections                                       *l* = −26→24
  --------------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.045   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.111                  H-atom parameters constrained
  *S* = 1.05                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0576*P*)^2^ + 0.2479*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  2710 reflections                      (Δ/σ)~max~ \< 0.001
  190 parameters                        Δρ~max~ = 0.27 e Å^−3^
  0 restraints                          Δρ~min~ = −0.22 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
  Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ \> 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
  ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ----- ------------- ------------ -------------- -------------------- --
        *x*           *y*          *z*            *U*~iso~\*/*U*~eq~   
  O1    0.6908 (3)    1.3470 (4)   0.16727 (9)    0.0252 (4)           
  O2    0.5696 (3)    0.5737 (5)   0.40854 (9)    0.0335 (5)           
  O3    0.3389 (3)    0.4666 (5)   0.47354 (9)    0.0338 (5)           
  N1    1.4552 (3)    0.7167 (6)   0.05402 (10)   0.0248 (5)           
  H1A   1.5039        0.8252       0.0236         0.030\*              
  H1B   1.5583        0.6443       0.0811         0.030\*              
  N2    0.6727 (3)    0.9187 (5)   0.21889 (9)    0.0193 (4)           
  H2    0.7097        0.7415       0.2215         0.023\*              
  N3    0.5305 (3)    1.0250 (5)   0.25824 (9)    0.0198 (4)           
  N4    0.3968 (3)    0.6017 (5)   0.42806 (10)   0.0241 (5)           
  C1    1.2814 (3)    0.8062 (6)   0.08357 (11)   0.0196 (5)           
  C2    1.2309 (3)    0.6722 (6)   0.14030 (11)   0.0194 (5)           
  H2A   1.3134        0.5234       0.1585         0.023\*              
  C3    1.0579 (3)    0.7606 (6)   0.16970 (11)   0.0190 (5)           
  H3    1.0271        0.6715       0.2078         0.023\*              
  C4    0.9293 (3)    0.9809 (6)   0.14297 (11)   0.0188 (5)           
  C5    0.9786 (3)    1.1101 (6)   0.08586 (11)   0.0200 (5)           
  H5    0.8938        1.2555       0.0671         0.024\*              
  C6    1.1522 (3)    1.0262 (6)   0.05623 (11)   0.0213 (5)           
  H6    1.1827        1.1162       0.0182         0.026\*              
  C7    0.7535 (3)    1.0973 (6)   0.17592 (11)   0.0189 (5)           
  C8    0.4572 (3)    0.8400 (6)   0.29566 (11)   0.0196 (5)           
  H8    0.5066        0.6525       0.2978         0.024\*              
  C9    0.2917 (3)    0.9327 (6)   0.33548 (11)   0.0188 (5)           
  C10   0.2529 (3)    0.8118 (6)   0.39485 (11)   0.0194 (5)           
  C11   0.0792 (4)    0.8859 (6)   0.42611 (11)   0.0230 (6)           
  H11   0.0555        0.7975       0.4650         0.028\*              
  C12   −0.0568 (4)   1.0909 (7)   0.39888 (12)   0.0264 (6)           
  H12   −0.1735       1.1405       0.4191         0.032\*              
  C13   −0.0189 (4)   1.2225 (6)   0.34132 (12)   0.0245 (5)           
  H13   −0.1085       1.3647       0.3236         0.029\*              
  C14   0.1523 (3)    1.1439 (6)   0.30967 (12)   0.0218 (5)           
  H14   0.1746        1.2331       0.2707         0.026\*              
  ----- ------------- ------------ -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- ------------- ------------- ------------- -------------- ------------ --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^      *U*^23^
  O1    0.0270 (9)    0.0148 (9)    0.0353 (10)   0.0046 (7)     0.0107 (7)   0.0022 (8)
  O2    0.0270 (8)    0.0396 (13)   0.0347 (10)   0.0120 (9)     0.0078 (7)   0.0073 (10)
  O3    0.0390 (10)   0.0295 (12)   0.0336 (10)   0.0006 (9)     0.0069 (8)   0.0107 (10)
  N1    0.0206 (9)    0.0285 (13)   0.0269 (10)   0.0033 (10)    0.0103 (7)   −0.0009 (11)
  N2    0.0187 (9)    0.0158 (10)   0.0247 (9)    0.0043 (8)     0.0083 (7)   0.0010 (9)
  N3    0.0182 (8)    0.0198 (11)   0.0223 (9)    0.0026 (8)     0.0061 (7)   −0.0025 (9)
  N4    0.0269 (10)   0.0202 (11)   0.0256 (10)   0.0020 (9)     0.0052 (8)   −0.0012 (10)
  C1    0.0170 (10)   0.0202 (13)   0.0222 (10)   −0.0017 (10)   0.0047 (8)   −0.0073 (11)
  C2    0.0182 (10)   0.0164 (13)   0.0236 (11)   0.0029 (9)     0.0021 (8)   −0.0020 (10)
  C3    0.0193 (10)   0.0154 (13)   0.0232 (11)   −0.0012 (9)    0.0060 (8)   −0.0008 (10)
  C4    0.0164 (9)    0.0189 (13)   0.0215 (10)   0.0004 (10)    0.0034 (7)   −0.0039 (10)
  C5    0.0204 (10)   0.0170 (12)   0.0227 (11)   0.0012 (10)    0.0024 (8)   0.0011 (11)
  C6    0.0232 (11)   0.0208 (13)   0.0208 (10)   −0.0012 (10)   0.0068 (8)   −0.0008 (10)
  C7    0.0181 (10)   0.0171 (12)   0.0222 (11)   −0.0012 (10)   0.0044 (8)   −0.0026 (11)
  C8    0.0188 (9)    0.0181 (12)   0.0223 (10)   0.0010 (10)    0.0038 (8)   −0.0014 (11)
  C9    0.0157 (9)    0.0153 (12)   0.0258 (11)   −0.0009 (9)    0.0045 (8)   −0.0028 (10)
  C10   0.0188 (10)   0.0153 (12)   0.0243 (11)   0.0014 (10)    0.0028 (8)   −0.0007 (11)
  C11   0.0251 (11)   0.0230 (15)   0.0223 (11)   −0.0018 (11)   0.0094 (8)   −0.0004 (11)
  C12   0.0203 (10)   0.0318 (16)   0.0283 (12)   0.0023 (11)    0.0084 (9)   −0.0031 (13)
  C13   0.0223 (10)   0.0216 (14)   0.0293 (12)   0.0035 (11)    0.0020 (9)   −0.0028 (12)
  C14   0.0215 (10)   0.0187 (14)   0.0254 (11)   0.0013 (10)    0.0035 (8)   0.0010 (11)
  ----- ------------- ------------- ------------- -------------- ------------ --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ------------------- -------------- ----------------------- -------------
  O1---C7             1.226 (3)      C4---C5                 1.380 (3)
  O2---N4             1.226 (3)      C4---C7                 1.474 (3)
  O3---N4             1.211 (3)      C5---C6                 1.378 (3)
  N1---C1             1.386 (3)      C5---H5                 0.9300
  N1---H1A            0.8900         C6---H6                 0.9300
  N1---H1B            0.8900         C8---C9                 1.467 (3)
  N2---C7             1.346 (3)      C8---H8                 0.9300
  N2---N3             1.368 (3)      C9---C10                1.386 (3)
  N2---H2             0.8600         C9---C14                1.397 (3)
  N3---C8             1.268 (3)      C10---C11               1.385 (3)
  N4---C10            1.470 (3)      C11---C12               1.378 (4)
  C1---C2             1.385 (3)      C11---H11               0.9300
  C1---C6             1.398 (3)      C12---C13               1.372 (4)
  C2---C3             1.379 (3)      C12---H12               0.9300
  C2---H2A            0.9300         C13---C14               1.381 (3)
  C3---C4             1.393 (3)      C13---H13               0.9300
  C3---H3             0.9300         C14---H14               0.9300
                                                             
  C1---N1---H1A       120.0          C5---C6---H6            119.9
  C1---N1---H1B       115.0          C1---C6---H6            119.9
  H1A---N1---H1B      111.2          O1---C7---N2            121.8 (2)
  C7---N2---N3        119.3 (2)      O1---C7---C4            122.1 (2)
  C7---N2---H2        120.4          N2---C7---C4            116.1 (2)
  N3---N2---H2        120.4          N3---C8---C9            118.3 (2)
  C8---N3---N2        115.1 (2)      N3---C8---H8            120.9
  O3---N4---O2        123.5 (2)      C9---C8---H8            120.9
  O3---N4---C10       118.12 (19)    C10---C9---C14          117.0 (2)
  O2---N4---C10       118.3 (2)      C10---C9---C8           125.2 (2)
  C2---C1---N1        119.9 (2)      C14---C9---C8           117.8 (2)
  C2---C1---C6        118.8 (2)      C9---C10---C11          121.9 (2)
  N1---C1---C6        121.0 (2)      C9---C10---N4           121.26 (19)
  C3---C2---C1        120.0 (2)      C11---C10---N4          116.7 (2)
  C3---C2---H2A       119.9          C12---C11---C10         119.5 (2)
  C1---C2---H2A       119.9          C12---C11---H11         120.2
  C2---C3---C4        121.2 (2)      C10---C11---H11         120.2
  C2---C3---H3        119.4          C11---C12---C13         119.7 (2)
  C4---C3---H3        119.4          C11---C12---H12         120.2
  C5---C4---C3        118.2 (2)      C13---C12---H12         120.2
  C5---C4---C7        119.0 (2)      C12---C13---C14         120.6 (2)
  C3---C4---C7        122.6 (2)      C12---C13---H13         119.7
  C6---C5---C4        121.0 (2)      C14---C13---H13         119.7
  C6---C5---H5        119.4          C13---C14---C9          121.2 (2)
  C4---C5---H5        119.4          C13---C14---H14         119.4
  C5---C6---C1        120.2 (2)      C9---C14---H14          119.4
                                                             
  C7---N2---N3---C8   177.7 (2)      N3---C8---C9---C10      −152.8 (2)
  N1---C1---C2---C3   −179.9 (2)     N3---C8---C9---C14      32.2 (3)
  C6---C1---C2---C3   −1.3 (4)       C14---C9---C10---C11    2.8 (4)
  C1---C2---C3---C4   0.9 (4)        C8---C9---C10---C11     −172.1 (2)
  C2---C3---C4---C5   0.1 (4)        C14---C9---C10---N4     −176.2 (2)
  C2---C3---C4---C7   −174.8 (2)     C8---C9---C10---N4      8.9 (4)
  C3---C4---C5---C6   −0.8 (4)       O3---N4---C10---C9      −167.6 (2)
  C7---C4---C5---C6   174.3 (2)      O2---N4---C10---C9      12.8 (4)
  C4---C5---C6---C1   0.3 (4)        O3---N4---C10---C11     13.3 (3)
  C2---C1---C6---C5   0.7 (4)        O2---N4---C10---C11     −166.2 (2)
  N1---C1---C6---C5   179.2 (2)      C9---C10---C11---C12    −1.9 (4)
  N3---N2---C7---O1   −6.0 (3)       N4---C10---C11---C12    177.2 (2)
  N3---N2---C7---C4   170.59 (19)    C10---C11---C12---C13   −0.5 (4)
  C5---C4---C7---O1   −22.4 (4)      C11---C12---C13---C14   1.8 (4)
  C3---C4---C7---O1   152.4 (2)      C12---C13---C14---C9    −0.7 (4)
  C5---C4---C7---N2   161.0 (2)      C10---C9---C14---C13    −1.6 (4)
  C3---C4---C7---N2   −24.1 (3)      C8---C9---C14---C13     173.8 (2)
  N2---N3---C8---C9   −175.25 (18)                           
  ------------------- -------------- ----------------------- -------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

  --------------------- --------- --------- ----------- ---------------
  *D*---H···*A*         *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  N1---H1*A*···N1^i^    0.89      2.44      3.287 (4)   162
  N1---H1*B*···O1^ii^   0.89      2.35      3.164 (3)   153
  N2---H2···O1^iii^     0.86      2.13      2.843 (3)   142
  C2---H2*A*···O1^ii^   0.93      2.56      3.329 (3)   140
  --------------------- --------- --------- ----------- ---------------

Symmetry codes: (i) −*x*+3, *y*+1/2, −*z*; (ii) *x*+1, *y*−1, *z*; (iii) *x*, *y*−1, *z*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------- --------- ------- ----------- -------------
  N1---H1*A*⋯N1^i^    0.89      2.44    3.287 (4)   162
  N1---H1*B*⋯O1^ii^   0.89      2.35    3.164 (3)   153
  N2---H2⋯O1^iii^     0.86      2.13    2.843 (3)   142
  C2---H2*A*⋯O1^ii^   0.93      2.56    3.329 (3)   140

Symmetry codes: (i) ; (ii) ; (iii) .
