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

For the medicinal applications of hydrazone compounds, see: Hillmer *et al.* ( 2010[@bb5]); Zhu *et al.* ( 2009[@bb15]); Jimenez-Pulido *et al.* ( 2008[@bb6]); Raj *et al.* ( 2007[@bb8]); Zhong *et al.* ( 2007[@bb14]).  For crystal structures of hydrazone compounds, see: Khaledi *et al.* ( 2009[@bb7]); Warad *et al.* ( 2009[@bb12]); Back *et al.* ( 2009[@bb1]); Vijayakumar *et al.* ( 2009[@bb11]).  For related structures, see: Cao (2009[@bb4]); Xu *et al.* ( 2009[@bb13]); Shafiq *et al.* ( 2009[@bb9]). 

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~15~H~13~BrN~2~O~4~·CH~4~O*M* *~r~* = 397.23Monoclinic,*a* = 7.4412 (4) Å*b* = 17.5287 (9) Å*c* = 12.5555 (8) Åβ = 91.200 (3)°*V* = 1637.31 (16) Å^3^*Z* = 4Mo *K*α radiationμ = 2.54 mm^−1^*T* = 298 K0.27 × 0.23 × 0.23 mm

### Data collection {#sec2.1.2}

Bruker SMART CCD area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2001[@bb2]) *T* ~min~ = 0.547, *T* ~max~ = 0.5939411 measured reflections3368 independent reflections2230 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.039

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.036*wR*(*F* ^2^) = 0.082*S* = 1.013368 reflections225 parameters1 restraintH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 0.24 e Å^−3^Δρ~min~ = −0.31 e Å^−3^

 {#d5e513}

Data collection: *SMART* (Bruker, 2007[@bb3]); cell refinement: *SAINT* (Bruker, 2007[@bb3]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXTL* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXTL*; molecular graphics: *SHELXTL*; software used to prepare material for publication: *SHELXTL*. 

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536810022063/ci5098sup1.cif](http://dx.doi.org/10.1107/S1600536810022063/ci5098sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536810022063/ci5098Isup2.hkl](http://dx.doi.org/10.1107/S1600536810022063/ci5098Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?ci5098&file=ci5098sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?ci5098sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?ci5098&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [CI5098](http://scripts.iucr.org/cgi-bin/sendsup?ci5098)). 

The authors acknowledge Taizhou University for financial support. 

Comment
=======

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer *et al.*,  2010; Zhu *et al.*,  2009; Jimenez-Pulido *et al.*,  2008; Raj *et al.*,  2007; Zhong *et al.*,  2007).  The study on the crystal structures of such compounds is of particular interest (Khaledi *et al.*,  2009; Warad *et al.*,  2009; Back *et al.*,  2009; Vijayakumar *et al.*,  2009).  We report herein the crystal structure of the title new hydrazone. 

The asymmetric unit of the title compound contains a benzohydrazide molecule and a methanol solvate molecule, as shown in Fig.  1.  The dihedral angle between the two benzene rings is 3.2 (2)°, indicating they are nearly coplanar.  Atom C15 deviates from the C9--C14 benzene ring by 0.188 (2) Å. All the bond lengths are comparable to those observed in related structures (Cao, 2009; Xu *et al.*,  2009; Shafiq *et al.*,  2009). 

In the crystal structure, the hydrazone and methanol molecules are linked through O---H···N, O---H···O, and N---H···O hydrogen bonds, to form a two-dimensional network parallel to the (101) (Fig.  2 and Table 1). 

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

The title compound was prepared by the condensation reaction of 5-bromosalicylaldehyde (0.05 mol, 10 g) and 4-hydroxy-3-methoxybenzohydrazide (0.05 mol, 9 g) in anhydrous methanol (200 ml) at ambient temperature.  Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the methanol solution for a period of 5 d.

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

Atom H2 was located in a difference map and refined isotropically, with the N--H distance restrained to 0.90 (1) Å; U~iso~(H2) was fixed to 0.08 Å^2^. The remaining H atoms were positioned geometrically and constrained to ride on their parent atoms, with C--H distances of 0.93--0.96 Å, O--H distances of 0.82 Å, and with *U*~iso~(H) = 1.2*U*~eq~(C) and 1.5*U*~eq~(C~methyl~ and O). 

Figures
=======

![ The molecular structure of the title compound.  Displacement ellipsoids are drawn at the 30% probability level.  Hydrogen atoms are shown as spheres of arbitrary radius.  Hydrogen bonds are shown as dashed lines.](e-66-o1662-fig1){#Fap1}

![ The molecular packing of the title compound, viewed along the a axis.  Hydrogen bonds are shown as dashed lines.  Hydrogen atoms not involved in hydrogen bonding have been omitted.](e-66-o1662-fig2){#Fap2}

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

  ----------------------------- ---------------------------------------
  C~15~H~13~BrN~2~O~4~·CH~4~O   *F*(000) = 808
  *M~r~* = 397.23               *D*~x~ = 1.611 Mg m^−3^
  Monoclinic, *P*2~1~/*n*       Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2yn           Cell parameters from 2105 reflections
  *a* = 7.4412 (4) Å            θ = 2.3--24.0°
  *b* = 17.5287 (9) Å           µ = 2.54 mm^−1^
  *c* = 12.5555 (8) Å           *T* = 298 K
  β = 91.200 (3)°               Block, colourless
  *V* = 1637.31 (16) Å^3^       0.27 × 0.23 × 0.23 mm
  *Z* = 4                       
  ----------------------------- ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker SMART CCD area-detector diffractometer                3368 independent reflections
  Radiation source: fine-focus sealed tube                     2230 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.039
  ω scans                                                      θ~max~ = 26.6°, θ~min~ = 2.0°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2001)   *h* = −9→9
  *T*~min~ = 0.547, *T*~max~ = 0.593                           *k* = −19→21
  9411 measured reflections                                    *l* = −13→15
  ------------------------------------------------------------ --------------------------------------

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*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.036   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.082                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.01                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0375*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  3368 reflections                      (Δ/σ)~max~ = 0.001
  225 parameters                        Δρ~max~ = 0.24 e Å^−3^
  1 restraint                           Δρ~min~ = −0.31 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~   
  Br1    0.18595 (5)   0.149648 (15)   0.52921 (3)    0.05687 (14)         
  N1     0.2299 (3)    0.51490 (11)    0.46909 (16)   0.0362 (5)           
  N2     0.2800 (3)    0.57506 (11)    0.53449 (16)   0.0370 (5)           
  O1     0.0923 (3)    0.44648 (10)    0.29416 (14)   0.0550 (6)           
  H1     0.1171        0.4831          0.3324         0.083\*              
  O2     0.2525 (3)    0.65966 (10)    0.40042 (15)   0.0508 (5)           
  O3     0.3700 (3)    0.91862 (9)     0.56842 (13)   0.0438 (5)           
  O4     0.5122 (3)    0.89035 (10)    0.75563 (14)   0.0513 (5)           
  H4     0.5720        0.8758          0.8073         0.077\*              
  O5     0.3071 (3)    0.51702 (11)    0.75469 (16)   0.0561 (6)           
  H5     0.2163        0.4979          0.7793         0.084\*              
  C1     0.1853 (4)    0.38040 (14)    0.4545 (2)     0.0363 (6)           
  C2     0.1173 (4)    0.38095 (15)    0.3500 (2)     0.0382 (6)           
  C3     0.0704 (4)    0.31294 (16)    0.3002 (2)     0.0468 (7)           
  H3     0.0236        0.3136          0.2309         0.056\*              
  C4     0.0928 (4)    0.24469 (15)    0.3524 (2)     0.0489 (8)           
  H4A    0.0631        0.1992          0.3182         0.059\*              
  C5     0.1593 (4)    0.24389 (14)    0.4555 (2)     0.0408 (7)           
  C6     0.2052 (4)    0.31014 (14)    0.5065 (2)     0.0393 (7)           
  H6     0.2498        0.3086          0.5763         0.047\*              
  C7     0.2359 (4)    0.44864 (14)    0.5118 (2)     0.0386 (7)           
  H7     0.2743        0.4443          0.5824         0.046\*              
  C8     0.2886 (3)    0.64661 (13)    0.4938 (2)     0.0329 (6)           
  C9     0.3473 (3)    0.70777 (13)    0.56902 (19)   0.0305 (6)           
  C10    0.3292 (3)    0.78280 (13)    0.5325 (2)     0.0328 (6)           
  H10    0.2810        0.7921          0.4648         0.039\*              
  C11    0.3827 (3)    0.84311 (12)    0.5964 (2)     0.0317 (6)           
  C12    0.4587 (4)    0.82893 (14)    0.69653 (19)   0.0336 (6)           
  C13    0.4745 (4)    0.75503 (13)    0.7325 (2)     0.0357 (6)           
  H13    0.5227        0.7457          0.8002         0.043\*              
  C14    0.4193 (3)    0.69455 (14)    0.66906 (19)   0.0350 (6)           
  H14    0.4310        0.6448          0.6941         0.042\*              
  C15    0.3218 (4)    0.93558 (16)    0.4607 (2)     0.0530 (8)           
  H15A   0.4045        0.9110          0.4141         0.079\*              
  H15B   0.3261        0.9898          0.4498         0.079\*              
  H15C   0.2022        0.9174          0.4455         0.079\*              
  C16    0.4575 (5)    0.4742 (2)      0.7866 (3)     0.0815 (11)          
  H16A   0.5649        0.5019          0.7707         0.122\*              
  H16B   0.4572        0.4264          0.7491         0.122\*              
  H16C   0.4536        0.4648          0.8618         0.122\*              
  H2     0.291 (4)     0.5653 (18)     0.6041 (10)    0.080\*              
  ------ ------------- --------------- -------------- -------------------- --

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

  ----- ------------- -------------- ------------- --------------- -------------- --------------
        *U*^11^       *U*^22^        *U*^33^       *U*^12^         *U*^13^        *U*^23^
  Br1   0.0671 (2)    0.02604 (16)   0.0779 (3)    −0.00003 (14)   0.01145 (17)   0.00364 (15)
  N1    0.0442 (14)   0.0265 (12)    0.0378 (13)   −0.0026 (10)    −0.0020 (10)   −0.0059 (10)
  N2    0.0540 (15)   0.0219 (11)    0.0346 (12)   −0.0025 (10)    −0.0071 (12)   −0.0032 (10)
  O1    0.0824 (16)   0.0330 (11)    0.0492 (12)   −0.0019 (11)    −0.0106 (11)   0.0004 (9)
  O2    0.0814 (16)   0.0344 (11)    0.0359 (11)   −0.0045 (10)    −0.0189 (10)   0.0029 (8)
  O3    0.0658 (14)   0.0215 (9)     0.0437 (11)   0.0019 (8)      −0.0123 (10)   0.0040 (8)
  O4    0.0815 (17)   0.0257 (10)    0.0458 (13)   0.0000 (9)      −0.0218 (11)   −0.0052 (8)
  O5    0.0667 (15)   0.0455 (12)    0.0558 (13)   −0.0083 (11)    −0.0048 (12)   0.0131 (10)
  C1    0.0394 (17)   0.0283 (13)    0.0413 (16)   −0.0033 (12)    0.0036 (13)    −0.0056 (12)
  C2    0.0431 (17)   0.0291 (13)    0.0424 (16)   −0.0010 (12)    0.0031 (13)    −0.0013 (12)
  C3    0.052 (2)     0.0403 (17)    0.0474 (17)   −0.0067 (14)    −0.0019 (14)   −0.0107 (14)
  C4    0.057 (2)     0.0309 (15)    0.059 (2)     −0.0117 (13)    0.0078 (16)    −0.0125 (14)
  C5    0.0424 (17)   0.0249 (14)    0.0554 (19)   −0.0001 (11)    0.0095 (14)    −0.0025 (13)
  C6    0.0464 (18)   0.0289 (14)    0.0428 (16)   −0.0031 (12)    0.0026 (14)    −0.0021 (12)
  C7    0.0520 (18)   0.0277 (14)    0.0358 (15)   −0.0001 (12)    −0.0031 (13)   −0.0012 (12)
  C8    0.0380 (16)   0.0268 (13)    0.0338 (15)   −0.0014 (11)    −0.0027 (12)   0.0006 (11)
  C9    0.0362 (16)   0.0212 (12)    0.0341 (14)   −0.0007 (10)    0.0015 (12)    0.0009 (10)
  C10   0.0365 (16)   0.0285 (13)    0.0331 (14)   0.0023 (11)     −0.0051 (12)   0.0039 (11)
  C11   0.0375 (16)   0.0179 (12)    0.0396 (15)   0.0030 (10)     −0.0003 (12)   0.0015 (11)
  C12   0.0395 (16)   0.0267 (13)    0.0343 (15)   −0.0007 (11)    −0.0030 (12)   −0.0031 (11)
  C13   0.0483 (18)   0.0307 (14)    0.0277 (13)   −0.0004 (12)    −0.0081 (12)   0.0018 (11)
  C14   0.0455 (17)   0.0242 (13)    0.0352 (15)   −0.0015 (11)    −0.0032 (13)   0.0059 (11)
  C15   0.077 (2)     0.0306 (15)    0.0507 (19)   −0.0022 (15)    −0.0197 (16)   0.0146 (13)
  C16   0.080 (3)     0.077 (3)      0.087 (3)     0.003 (2)       −0.015 (2)     0.018 (2)
  ----- ------------- -------------- ------------- --------------- -------------- --------------

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

  ---------------- ------------- ------------------- -----------
  Br1---C5         1.902 (3)     C4---H4A            0.93
  N1---C7          1.279 (3)     C5---C6             1.367 (3)
  N1---N2          1.383 (3)     C6---H6             0.93
  N2---C8          1.356 (3)     C7---H7             0.93
  N2---H2          0.893 (10)    C8---C9             1.489 (3)
  O1---C2          1.357 (3)     C9---C14            1.375 (3)
  O1---H1          0.82          C9---C10            1.399 (3)
  O2---C8          1.218 (3)     C10---C11           1.381 (3)
  O3---C11         1.372 (3)     C10---H10           0.93
  O3---C15         1.423 (3)     C11---C12           1.390 (3)
  O4---C12         1.362 (3)     C12---C13           1.376 (3)
  O4---H4          0.82          C13---C14           1.383 (3)
  O5---C16         1.400 (4)     C13---H13           0.93
  O5---H5          0.82          C14---H14           0.93
  C1---C2          1.395 (4)     C15---H15A          0.96
  C1---C6          1.401 (4)     C15---H15B          0.96
  C1---C7          1.442 (3)     C15---H15C          0.96
  C2---C3          1.388 (4)     C16---H16A          0.96
  C3---C4          1.373 (4)     C16---H16B          0.96
  C3---H3          0.93          C16---H16C          0.96
  C4---C5          1.376 (4)                         
                                                     
  C7---N1---N2     115.9 (2)     N2---C8---C9        116.2 (2)
  C8---N2---N1     119.7 (2)     C14---C9---C10      119.4 (2)
  C8---N2---H2     123 (2)       C14---C9---C8       124.2 (2)
  N1---N2---H2     117 (2)       C10---C9---C8       116.4 (2)
  C2---O1---H1     109.5         C11---C10---C9      120.3 (2)
  C11---O3---C15   117.37 (19)   C11---C10---H10     119.9
  C12---O4---H4    109.5         C9---C10---H10      119.9
  C16---O5---H5    109.5         O3---C11---C10      124.9 (2)
  C2---C1---C6     118.5 (2)     O3---C11---C12      115.4 (2)
  C2---C1---C7     123.3 (2)     C10---C11---C12     119.7 (2)
  C6---C1---C7     118.2 (2)     O4---C12---C13      122.9 (2)
  O1---C2---C3     117.6 (2)     O4---C12---C11      117.4 (2)
  O1---C2---C1     122.3 (2)     C13---C12---C11     119.7 (2)
  C3---C2---C1     120.0 (3)     C12---C13---C14     120.6 (2)
  C4---C3---C2     120.4 (3)     C12---C13---H13     119.7
  C4---C3---H3     119.8         C14---C13---H13     119.7
  C2---C3---H3     119.8         C9---C14---C13      120.2 (2)
  C3---C4---C5     119.7 (3)     C9---C14---H14      119.9
  C3---C4---H4A    120.1         C13---C14---H14     119.9
  C5---C4---H4A    120.1         O3---C15---H15A     109.5
  C6---C5---C4     120.9 (3)     O3---C15---H15B     109.5
  C6---C5---Br1    119.1 (2)     H15A---C15---H15B   109.5
  C4---C5---Br1    119.9 (2)     O3---C15---H15C     109.5
  C5---C6---C1     120.3 (2)     H15A---C15---H15C   109.5
  C5---C6---H6     119.8         H15B---C15---H15C   109.5
  C1---C6---H6     119.8         O5---C16---H16A     109.5
  N1---C7---C1     122.5 (2)     O5---C16---H16B     109.5
  N1---C7---H7     118.7         H16A---C16---H16B   109.5
  C1---C7---H7     118.7         O5---C16---H16C     109.5
  O2---C8---N2     121.7 (2)     H16A---C16---H16C   109.5
  O2---C8---C9     122.1 (2)     H16B---C16---H16C   109.5
  ---------------- ------------- ------------------- -----------

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

  ------------------ ---------- ---------- ----------- ---------------
  *D*---H···*A*      *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  N2---H2···O5       0.89 (1)   2.07 (1)   2.949 (3)   167 (3)
  O1---H1···N1       0.82       1.98       2.686 (3)   145
  O4---H4···O2^i^    0.82       1.87       2.671 (3)   166
  O5---H5···O3^ii^   0.82       2.46       3.125 (3)   139
  O5---H5···O4^ii^   0.82       2.57       3.252 (3)   141
  ------------------ ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*      *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  ---------------- ---------- ---------- ----------- -------------
  N2---H2⋯O5       0.89 (1)   2.07 (1)   2.949 (3)   167 (3)
  O1---H1⋯N1       0.82       1.98       2.686 (3)   145
  O4---H4⋯O2^i^    0.82       1.87       2.671 (3)   166
  O5---H5⋯O3^ii^   0.82       2.46       3.125 (3)   139
  O5---H5⋯O4^ii^   0.82       2.57       3.252 (3)   141

Symmetry codes: (i) ; (ii) .