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

For azine compounds containing both a diimine linkage and N---N bonding, see: Kesslen *et al.* (1999[@bb5]); Kundu *et al.* (2005[@bb6]). For related structures, see: Glaser *et al.* (1995[@bb3]); Hunig *et al.* (2000[@bb4]).

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

 {#sec2.1}

### Crystal data {#sec2.1.1}

C~18~H~18~Cl~2~N~2~O~2~*M* *~r~* = 365.24Orthorhombic,*a* = 7.9030 (19) Å*b* = 27.862 (7) Å*c* = 3.9819 (10) Å*V* = 876.8 (4) Å^3^*Z* = 2Mo *K*α radiationμ = 0.38 mm^−1^*T* = 295 K0.22 × 0.16 × 0.12 mm

### Data collection {#sec2.1.2}

Bruker APEXII CCD area detector diffractometerAbsorption correction: multi-scan (*SADABS*; Sheldrick, 2003[@bb7]) *T* ~min~ = 0.921, *T* ~max~ = 0.9564469 measured reflections1566 independent reflections1417 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.019

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.036*wR*(*F* ^2^) = 0.129*S* = 1.011566 reflections111 parametersH-atom parameters constrainedΔρ~max~ = 0.12 e Å^−3^Δρ~min~ = −0.22 e Å^−3^Absolute structure: Flack (1983[@bb2]), 592 Friedel pairsFlack parameter: 0.08 (12)

 {#d5e431}

Data collection: *APEX2* (Bruker, 2005[@bb1]); cell refinement: *SAINT* (Bruker, 2005[@bb1]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb8]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb8]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb8]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablocks global, I. DOI: [10.1107/S1600536809048351/fl2273sup1.cif](http://dx.doi.org/10.1107/S1600536809048351/fl2273sup1.cif)

Structure factors: contains datablocks I. DOI: [10.1107/S1600536809048351/fl2273Isup2.hkl](http://dx.doi.org/10.1107/S1600536809048351/fl2273Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?fl2273&file=fl2273sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?fl2273sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?fl2273&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [FL2273](http://scripts.iucr.org/cgi-bin/sendsup?fl2273)).

This project was supported by the Postgraduate Foundation of Taishan University (No.Y05--2-09)

Comment
=======

Recently, a number of azine compounds containing both a diimine linkage and N---N bonding have been investigated in terms of their crystallography and coordination chemistry (Kundu *et al.*, 2005; Kesslen *et al.*, 1999). As an extension of the work on the structural characterization of azine derivatives, the title compound, (I),was synthesized and its crystal structure is reported here.

The molecule lies on a crystallogrpahic 2-fold axis passing through the mid-point of the N-N bond to give 1/2 molecule per asymmetric unit. (Fig. 1). The dihedral angle between the two aromatic rings is 44.33 (4)°. The N atom and the phenyl ring liie on opposite side of the C8=N1 bond to give an (E, E) conformation with respect to the C8=N1 bond ( and its symmetry related C8*a*=N1a double bond (Fig. 1.). This configuration agrees with those commonly found in similar compounds (Glaser *et al.*, 1995; Hunig *et al.*, 2000). Intermolecular C---H···O interactions link the molecules into columns along the c axis (Table 1, Fig. 2).

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

An ethanol solution (30 ml) of hydrazine (0.02 mol) and 1-(5-chloro-2-methoxyphenyl)ethanone (0.04 mol) was refluxed and stirred for 6 h; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Colourless crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in acetone.

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

All H atoms were positioned geometrically and treated as riding on their parent atoms,with *C*---*H*(methyl) = 0.96 Å, C---H(aromatic) = 0.93 Å, and with *U*~iso~(H) =1.5*U*~eq~(C~methyl~) and 1.2*U*~eq~(C~aromatic~).

Figures
=======

![The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.](e-65-o3185-fig1){#Fap1}

![The crystal packing of (I) , Dashed lines show intermolecular C---H···O interactions .](e-65-o3185-fig2){#Fap2}

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

  ---------------------------- ---------------------------------------
  C~18~H~18~Cl~2~N~2~O~2~      *F*(000) = 380
  *M~r~* = 365.24              *D*~x~ = 1.383 Mg m^−3^
  Orthorhombic, *P*2~1~2~1~2   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: P 2 2ab         Cell parameters from 2313 reflections
  *a* = 7.9030 (19) Å          θ = 2.7--27.8°
  *b* = 27.862 (7) Å           µ = 0.38 mm^−1^
  *c* = 3.9819 (10) Å          *T* = 295 K
  *V* = 876.8 (4) Å^3^         Block, colourless
  *Z* = 2                      0.22 × 0.16 × 0.12 mm
  ---------------------------- ---------------------------------------

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

  --------------------------------------------------------------- --------------------------------------
  Bruker APEXII CCD area detector diffractometer                  1566 independent reflections
  Radiation source: fine-focus sealed tube                        1417 reflections with *I* \> 2σ(*I*)
  graphite                                                        *R*~int~ = 0.019
  phi and ω scans                                                 θ~max~ = 25.0°, θ~min~ = 1.5°
  Absorption correction: multi-scan (*SADABS*; Sheldrick, 2003)   *h* = −9→8
  *T*~min~ = 0.921, *T*~max~ = 0.956                              *k* = −33→32
  4469 measured reflections                                       *l* = −4→4
  --------------------------------------------------------------- --------------------------------------

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

  ---------------------------------------------------------------- ------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                                             Secondary atom site location: difference Fourier map
  Least-squares matrix: full                                       Hydrogen site location: inferred from neighbouring sites
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.036                              H-atom parameters constrained
  *wR*(*F*^2^) = 0.129                                             *w* = 1/\[σ^2^(*F*~o~^2^) + (0.1019*P*)^2^ + 0.021*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.01                                                       (Δ/σ)~max~ \< 0.001
  1566 reflections                                                 Δρ~max~ = 0.12 e Å^−3^
  111 parameters                                                   Δρ~min~ = −0.22 e Å^−3^
  0 restraints                                                     Absolute structure: Flack (1983), 592 Friedel pairs
  Primary atom site location: structure-invariant direct methods   Flack parameter: 0.08 (12)
  ---------------------------------------------------------------- ------------------------------------------------------------------------------------------------

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~   
  Cl1   0.35358 (10)   0.29469 (2)    0.1116 (2)   0.0643 (3)           
  O1    0.9306 (2)     0.40920 (6)    0.5876 (6)   0.0520 (5)           
  N1    0.5044 (3)     0.47464 (6)    0.4965 (5)   0.0367 (5)           
  C1    0.6541 (3)     0.40440 (7)    0.3671 (6)   0.0333 (5)           
  C2    0.8000 (3)     0.38071 (8)    0.4798 (6)   0.0373 (6)           
  C3    0.8050 (4)     0.33068 (10)   0.4871 (7)   0.0487 (7)           
  H3    0.9006         0.3150         0.5674       0.058\*              
  C4    0.6670 (3)     0.30434 (8)    0.3743 (7)   0.0468 (7)           
  H4    0.6702         0.2710         0.3770       0.056\*              
  C5    0.5261 (4)     0.32784 (9)    0.2588 (7)   0.0429 (6)           
  C6    0.5175 (3)     0.37744 (8)    0.2532 (6)   0.0381 (6)           
  H6    0.4208         0.3927         0.1736       0.046\*              
  C7    1.0770 (4)     0.38654 (12)   0.7221 (9)   0.0611 (8)           
  H7A   1.0453         0.3671         0.9111       0.092\*              
  H7B   1.1565         0.4106         0.7929       0.092\*              
  H7C   1.1279         0.3667         0.5532       0.092\*              
  C8    0.6407 (3)     0.45789 (8)    0.3653 (6)   0.0330 (5)           
  C9    0.7746 (3)     0.48801 (9)    0.2056 (7)   0.0413 (6)           
  H9A   0.7244         0.5081         0.0369       0.062\*              
  H9B   0.8580         0.4676         0.1039       0.062\*              
  H9C   0.8274         0.5077         0.3734       0.062\*              
  ----- -------------- -------------- ------------ -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Cl1   0.0758 (5)    0.0434 (4)    0.0738 (5)    −0.0196 (3)    −0.0095 (5)    −0.0004 (4)
  O1    0.0404 (9)    0.0499 (10)   0.0656 (13)   0.0104 (8)     −0.0170 (10)   −0.0051 (10)
  N1    0.0331 (10)   0.0273 (9)    0.0497 (12)   0.0040 (8)     −0.0013 (9)    0.0009 (9)
  C1    0.0368 (12)   0.0316 (12)   0.0315 (11)   0.0055 (9)     0.0014 (11)    0.0012 (9)
  C2    0.0404 (13)   0.0386 (12)   0.0329 (12)   0.0102 (10)    −0.0014 (10)   −0.0024 (10)
  C3    0.0568 (16)   0.0408 (13)   0.0485 (15)   0.0213 (12)    −0.0006 (13)   0.0047 (12)
  C4    0.0618 (17)   0.0286 (11)   0.0500 (15)   0.0080 (11)    0.0084 (15)    0.0008 (11)
  C5    0.0567 (16)   0.0327 (12)   0.0392 (13)   −0.0037 (12)   0.0022 (12)    0.0010 (10)
  C6    0.0382 (13)   0.0343 (12)   0.0420 (13)   0.0049 (10)    −0.0002 (11)   0.0035 (10)
  C7    0.0409 (14)   0.082 (2)     0.0605 (19)   0.0158 (15)    −0.0150 (13)   −0.0022 (17)
  C8    0.0340 (11)   0.0311 (11)   0.0337 (11)   0.0024 (9)     −0.0040 (11)   −0.0019 (9)
  C9    0.0400 (12)   0.0362 (13)   0.0475 (15)   −0.0018 (11)   0.0057 (11)    −0.0039 (11)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  -------------------- ------------- ---------------------- --------------
  Cl1---C5             1.748 (3)     C4---C5                1.371 (4)
  O1---C2              1.371 (3)     C4---H4                0.9300
  O1---C7              1.422 (3)     C5---C6                1.384 (3)
  N1---C8              1.285 (3)     C6---H6                0.9300
  N1---N1^i^           1.415 (3)     C7---H7A               0.9600
  C1---C6              1.391 (3)     C7---H7B               0.9600
  C1---C2              1.403 (3)     C7---H7C               0.9600
  C1---C8              1.494 (3)     C8---C9                1.493 (3)
  C2---C3              1.395 (4)     C9---H9A               0.9600
  C3---C4              1.389 (4)     C9---H9B               0.9600
  C3---H3              0.9300        C9---H9C               0.9600
                                                            
  C2---O1---C7         118.2 (2)     C5---C6---H6           120.1
  C8---N1---N1^i^      113.8 (2)     C1---C6---H6           120.1
  C6---C1---C2         119.2 (2)     O1---C7---H7A          109.5
  C6---C1---C8         118.9 (2)     O1---C7---H7B          109.5
  C2---C1---C8         121.9 (2)     H7A---C7---H7B         109.5
  O1---C2---C3         123.4 (2)     O1---C7---H7C          109.5
  O1---C2---C1         116.53 (19)   H7A---C7---H7C         109.5
  C3---C2---C1         120.0 (2)     H7B---C7---H7C         109.5
  C4---C3---C2         119.9 (2)     N1---C8---C9           124.3 (2)
  C4---C3---H3         120.0         N1---C8---C1           114.8 (2)
  C2---C3---H3         120.0         C9---C8---C1           120.9 (2)
  C5---C4---C3         119.6 (2)     C8---C9---H9A          109.5
  C5---C4---H4         120.2         C8---C9---H9B          109.5
  C3---C4---H4         120.2         H9A---C9---H9B         109.5
  C4---C5---C6         121.5 (3)     C8---C9---H9C          109.5
  C4---C5---Cl1        119.57 (19)   H9A---C9---H9C         109.5
  C6---C5---Cl1        118.9 (2)     H9B---C9---H9C         109.5
  C5---C6---C1         119.7 (2)                            
                                                            
  C7---O1---C2---C3    −1.7 (4)      C4---C5---C6---C1      −0.1 (4)
  C7---O1---C2---C1    176.4 (2)     Cl1---C5---C6---C1     −179.54 (19)
  C6---C1---C2---O1    179.7 (2)     C2---C1---C6---C5      1.3 (4)
  C8---C1---C2---O1    −0.2 (3)      C8---C1---C6---C5      −178.8 (2)
  C6---C1---C2---C3    −2.1 (4)      N1^i^---N1---C8---C9   −3.8 (3)
  C8---C1---C2---C3    178.0 (2)     N1^i^---N1---C8---C1   179.13 (16)
  O1---C2---C3---C4    179.8 (2)     C6---C1---C8---N1      48.8 (3)
  C1---C2---C3---C4    1.7 (4)       C2---C1---C8---N1      −131.3 (2)
  C2---C3---C4---C5    −0.5 (4)      C6---C1---C8---C9      −128.4 (2)
  C3---C4---C5---C6    −0.3 (4)      C2---C1---C8---C9      51.5 (3)
  C3---C4---C5---Cl1   179.2 (2)                            
  -------------------- ------------- ---------------------- --------------

Symmetry codes: (i) −*x*+1, −*y*+1, *z*.

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

  ------------------- --------- --------- ----------- ---------------
  *D*---H···*A*       *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C9---H9B···O1^ii^   0.96      2.68      3.521 (3)   146
  ------------------- --------- --------- ----------- ---------------

Symmetry codes: (ii) *x*, *y*, *z*−1.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*        *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ------------------ --------- ------- ----------- -------------
  C9---H9*B*⋯O1^i^   0.96      2.68    3.521 (3)   146

Symmetry code: (i) .
