organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N′-[1-(4-Chloro­phen­yl)ethyl­­idene]benzo­hydrazide

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: drzengsy@163.com

(Received 30 September 2011; accepted 17 October 2011; online 29 October 2011)

In the title mol­ecule, C15H13ClN2O, the two benzene rings form a dihedral angle of 5.48 (4)°. In the crystal, N—H⋯O hydrogen bonds link mol­ecules related by translation along the a axis into chains, which are further aggregated into layers parallel to the ac plane through weak C—H⋯O and C—H⋯N inter­actions.

Related literature

For applications of Schiff base derivatives and their complexes, see: Chavan et al. (2011[Chavan, S. S., Sawant, S. K., Sawant, V. A. & Lahiri, G. K. (2011). Inorg. Chem. Commun. 14, 1373-1376.]); Ray et al. (2011[Ray, A., Rosair, G. M., Pilet, G., Dede, B., Gomez-Garcia, C. J., Signorella, S., Bellu, S. & Mitra, S. (2011). Inorg. Chim. Acta, 375, 20-30.]). For the crystal structures of related compounds, see: Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]); Fun et al. (2008[Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13ClN2O

  • Mr = 272.72

  • Monoclinic, P 21 /c

  • a = 5.0714 (6) Å

  • b = 31.430 (3) Å

  • c = 8.4128 (7) Å

  • β = 94.388 (1)°

  • V = 1337.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 298 K

  • 0.40 × 0.30 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD area-etector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.897, Tmax = 0.967

  • 6717 measured reflections

  • 2322 independent reflections

  • 711 reflections with I > 2σ(I)

  • Rint = 0.156

Refinement
  • R[F2 > 2σ(F2)] = 0.089

  • wR(F2) = 0.205

  • S = 1.01

  • 2322 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 2.32 3.067 (6) 145
C9—H9C⋯N2i 0.96 2.53 3.452 (8) 162
C15—H15⋯O1ii 0.93 2.61 3.483 (7) 157
Symmetry codes: (i) x-1, y, z; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Schiff bases have various applications in the study of biological processes and in pharmacology (Chavan et al., 2011; Ray et al., 2011). We report here the crystal structure of the title Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie, 2008; Fun et al., 2008). The CN (C8N2) bond length in the molecule is 1.270 (7) Å showing the double-bond character. Meanwhile, the dihedral angle between the benzene rings C2–C7 and C10–C15 is 5.48 (4)°.

In the crystal stucture, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis a into chains, which are further aggregated into layers parallel to ac plane through the weak C—H···O(N) interactions (Table 1).

Related literature top

For applications of Schiff base derivatives and their complexes, see: Chavan et al. (2011); Ray et al. (2011). For the crystal structures of related compounds, see: Nie (2008); Fun et al. (2008).

Experimental top

Benzohydrazide (5.0 mmol), 20 ml ethanol and 4-chloroacetophenone (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid.

Refinement top

All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H 0.93–0.96 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2–1.5Ueq(C,N).

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of (I) showing the atomic numbering and 30% probability displacement ellipsoids.
N'-[1-(4-Chlorophenyl)ethylidene]benzohydrazide top
Crystal data top
C15H13ClN2OF(000) = 568
Mr = 272.72Dx = 1.355 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.0714 (6) ÅCell parameters from 385 reflections
b = 31.430 (3) Åθ = 2.6–18.2°
c = 8.4128 (7) ŵ = 0.28 mm1
β = 94.388 (1)°T = 298 K
V = 1337.0 (2) Å3Needle, colourless
Z = 40.40 × 0.30 × 0.12 mm
Data collection top
Bruker SMART APEX CCD area-etector
diffractometer
2322 independent reflections
Radiation source: fine-focus sealed tube711 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.156
ϕ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 56
Tmin = 0.897, Tmax = 0.967k = 3637
6717 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.089Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0367P)2]
where P = (Fo2 + 2Fc2)/3
2322 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C15H13ClN2OV = 1337.0 (2) Å3
Mr = 272.72Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.0714 (6) ŵ = 0.28 mm1
b = 31.430 (3) ÅT = 298 K
c = 8.4128 (7) Å0.40 × 0.30 × 0.12 mm
β = 94.388 (1)°
Data collection top
Bruker SMART APEX CCD area-etector
diffractometer
2322 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
711 reflections with I > 2σ(I)
Tmin = 0.897, Tmax = 0.967Rint = 0.156
6717 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0890 restraints
wR(F2) = 0.205H-atom parameters constrained
S = 1.01Δρmax = 0.31 e Å3
2322 reflectionsΔρmin = 0.24 e Å3
173 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
N10.1612 (9)0.19148 (16)0.2256 (5)0.0650 (15)
H10.00120.18410.19750.078*
N20.2278 (10)0.23422 (17)0.2404 (6)0.0623 (14)
O10.5839 (9)0.17193 (12)0.2838 (5)0.0807 (14)
Cl10.3944 (4)0.44187 (5)0.2883 (3)0.1218 (10)
C10.3466 (15)0.1622 (2)0.2551 (7)0.0666 (18)
C20.2677 (14)0.11724 (19)0.2454 (9)0.072 (2)
C30.4245 (14)0.0876 (2)0.3254 (8)0.091 (2)
H30.57940.09610.38330.109*
C40.354 (2)0.0454 (2)0.3206 (11)0.115 (3)
H40.45910.02590.37900.138*
C50.135 (2)0.0313 (3)0.2335 (14)0.128 (4)
H50.08810.00270.23170.154*
C60.0118 (16)0.0606 (3)0.1496 (12)0.130 (3)
H60.16060.05200.08640.156*
C70.0548 (14)0.1034 (2)0.1558 (9)0.097 (3)
H70.05020.12280.09660.116*
C80.0706 (13)0.2614 (2)0.1746 (8)0.0627 (17)
C90.1756 (12)0.24969 (16)0.0768 (8)0.083 (2)
H9A0.14670.22400.01900.124*
H9B0.22300.27220.00300.124*
H9C0.31610.24530.14530.124*
C100.1404 (12)0.30593 (19)0.2013 (8)0.0571 (17)
C110.3468 (14)0.3164 (2)0.3061 (9)0.088 (2)
H110.43850.29480.36190.106*
C120.4259 (13)0.3580 (2)0.3330 (8)0.090 (2)
H120.57110.36390.40400.108*
C130.2931 (16)0.39022 (19)0.2566 (9)0.0744 (19)
C140.0872 (14)0.3808 (2)0.1543 (9)0.083 (2)
H140.00430.40270.09990.100*
C150.0069 (12)0.3392 (2)0.1273 (7)0.077 (2)
H150.14040.33370.05760.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.046 (3)0.067 (4)0.079 (4)0.003 (3)0.015 (3)0.008 (3)
N20.055 (4)0.070 (4)0.060 (3)0.001 (3)0.010 (3)0.001 (3)
O10.063 (3)0.077 (3)0.100 (4)0.000 (2)0.009 (3)0.002 (2)
Cl10.1365 (18)0.0779 (13)0.147 (2)0.0169 (12)0.0117 (16)0.0044 (13)
C10.062 (5)0.072 (5)0.066 (5)0.001 (5)0.007 (5)0.001 (4)
C20.051 (5)0.060 (5)0.106 (6)0.002 (4)0.007 (5)0.006 (4)
C30.099 (6)0.081 (5)0.088 (6)0.012 (5)0.016 (5)0.008 (5)
C40.142 (9)0.064 (6)0.138 (8)0.013 (6)0.001 (7)0.009 (5)
C50.109 (8)0.072 (6)0.208 (12)0.015 (6)0.043 (8)0.014 (7)
C60.098 (7)0.089 (7)0.201 (11)0.007 (6)0.003 (7)0.030 (7)
C70.056 (5)0.078 (5)0.155 (8)0.011 (4)0.007 (5)0.029 (5)
C80.039 (4)0.076 (5)0.071 (5)0.002 (4)0.009 (4)0.003 (4)
C90.071 (5)0.079 (4)0.096 (6)0.004 (4)0.009 (5)0.014 (4)
C100.033 (4)0.066 (5)0.070 (5)0.001 (3)0.002 (4)0.007 (4)
C110.087 (6)0.061 (5)0.112 (6)0.011 (4)0.019 (5)0.001 (4)
C120.085 (5)0.087 (5)0.092 (6)0.005 (5)0.035 (5)0.016 (5)
C130.066 (5)0.068 (5)0.090 (5)0.006 (4)0.010 (5)0.006 (4)
C140.073 (5)0.069 (5)0.105 (6)0.006 (4)0.010 (5)0.027 (4)
C150.065 (5)0.069 (5)0.094 (6)0.004 (4)0.016 (4)0.008 (4)
Geometric parameters (Å, º) top
N1—C11.326 (6)C7—H70.9300
N1—N21.388 (5)C8—C101.458 (7)
N1—H10.8600C8—C91.488 (8)
N2—C81.266 (6)C9—H9A0.9600
O1—C11.248 (6)C9—H9B0.9600
Cl1—C131.717 (6)C9—H9C0.9600
C1—C21.468 (7)C10—C111.357 (7)
C2—C71.341 (8)C10—C151.369 (7)
C2—C31.368 (8)C11—C121.382 (7)
C3—C41.374 (9)C11—H110.9300
C3—H30.9300C12—C131.351 (8)
C4—C51.357 (9)C12—H120.9300
C4—H40.9300C13—C141.335 (8)
C5—C61.350 (10)C14—C151.383 (7)
C5—H50.9300C14—H140.9300
C6—C71.385 (8)C15—H150.9300
C6—H60.9300
C1—N1—N2119.4 (5)N2—C8—C9123.3 (6)
C1—N1—H1120.3C10—C8—C9120.4 (6)
N2—N1—H1120.3C8—C9—H9A109.5
C8—N2—N1118.2 (5)C8—C9—H9B109.5
O1—C1—N1121.7 (6)H9A—C9—H9B109.5
O1—C1—C2120.1 (6)C8—C9—H9C109.5
N1—C1—C2118.1 (6)H9A—C9—H9C109.5
C7—C2—C3117.9 (6)H9B—C9—H9C109.5
C7—C2—C1123.2 (7)C11—C10—C15116.1 (6)
C3—C2—C1118.8 (7)C11—C10—C8120.0 (6)
C2—C3—C4120.1 (7)C15—C10—C8123.9 (6)
C2—C3—H3120.0C10—C11—C12122.4 (6)
C4—C3—H3120.0C10—C11—H11118.8
C5—C4—C3122.3 (8)C12—C11—H11118.8
C5—C4—H4118.9C13—C12—C11120.2 (6)
C3—C4—H4118.9C13—C12—H12119.9
C6—C5—C4116.9 (9)C11—C12—H12119.9
C6—C5—H5121.5C14—C13—C12118.6 (6)
C4—C5—H5121.5C14—C13—Cl1121.3 (6)
C5—C6—C7121.4 (9)C12—C13—Cl1120.1 (7)
C5—C6—H6119.3C13—C14—C15121.4 (6)
C7—C6—H6119.3C13—C14—H14119.3
C2—C7—C6121.3 (7)C15—C14—H14119.3
C2—C7—H7119.4C10—C15—C14121.2 (6)
C6—C7—H7119.4C10—C15—H15119.4
N2—C8—C10116.3 (6)C14—C15—H15119.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.323.067 (6)145
C9—H9C···N2i0.962.533.452 (8)162
C15—H15···O1ii0.932.613.483 (7)157
Symmetry codes: (i) x1, y, z; (ii) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC15H13ClN2O
Mr272.72
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)5.0714 (6), 31.430 (3), 8.4128 (7)
β (°) 94.388 (1)
V3)1337.0 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.40 × 0.30 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD area-etector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.897, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
6717, 2322, 711
Rint0.156
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.089, 0.205, 1.01
No. of reflections2322
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.24

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.323.067 (6)145.4
C9—H9C···N2i0.962.533.452 (8)161.5
C15—H15···O1ii0.932.613.483 (7)157.0
Symmetry codes: (i) x1, y, z; (ii) x1, y+1/2, z1/2.
 

Acknowledgements

The authors acknowledge financial support from Liaocheng University.

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChavan, S. S., Sawant, S. K., Sawant, V. A. & Lahiri, G. K. (2011). Inorg. Chem. Commun. 14, 1373–1376.  Web of Science CSD CrossRef CAS Google Scholar
First citationFun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNie, Y. (2008). Acta Cryst. E64, o471.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRay, A., Rosair, G. M., Pilet, G., Dede, B., Gomez-Garcia, C. J., Signorella, S., Bellu, S. & Mitra, S. (2011). Inorg. Chim. Acta, 375, 20–30.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds