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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-N′-[(E)-3-Phenyl­allyl­­idene]benzo­hydrazide

aMOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, People's Republic of China, and bThe First Affiliated Hospital of Hunan University of Chinese Medicine, Changsha, 410007, People's Republic of China
*Correspondence e-mail: zhang_heming88@yahoo.com.cn

(Received 10 December 2011; accepted 13 December 2011; online 17 December 2011)

In the title mol­ecule, C16H14N2O, the dihedral angle between the two phenyl rings is 23.5 (6)°. In the crystal, N—H—O hydrogen bonds link mol­ecules into chains running along the a axis.

Related literature

For general background to the applications of Schiff bases in the pharmaceutical and agrochemical fields, see: Bernardino et al. (2006[Bernardino, A. M. R., Gomes, A. O., Charret, K. S., Freita, A. C. C., Machado, G. M. C., Canto-Cavalheiro, M. M., Leon, L. L. & Amaral, V. F. (2006). Eur. J. Med. Chem. 41, 80-87.]); Zhang et al. (2008[Zhang, H. Q., Li, J. Z., Zhang, Y. & Zhang, D. (2008). Chin. J. Inorg. Chem. 24, 990-993.]). For related structures, see: Ji & Shi (2008[Ji, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o1918.]); He & Liu (2005[He, Y.-Z. & Liu, D.-Z. (2005). Acta Cryst. E61, o3855-o3856.]); Zhen & Han (2005[Zhen, X.-L. & Han, J.-R. (2005). Acta Cryst. E61, o4360-o4361.]); Zhang et al. (2007[Zhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N2O

  • Mr = 250.29

  • Orthorhombic, P n a 21

  • a = 8.427 (3) Å

  • b = 10.439 (4) Å

  • c = 15.724 (6) Å

  • V = 1383.2 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.16 × 0.13 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 6868 measured reflections

  • 1761 independent reflections

  • 1361 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.096

  • S = 1.01

  • 1761 reflections

  • 176 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.09 e Å−3

  • Δρmin = −0.12 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O1i 0.88 (2) 2.05 (2) 2.898 (3) 161 (2)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; 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 attracted much attention due to their various activities in pharmaceutical and agrochemical fields (Bernardino et al., 2006; Zhang et al., 2008). We now report the synthesis and structure of the title compound, (I).

In (I) (Fig. 1), the Schiff base molecule adopts an E geometry with respect to the C=N bond. All bond lengths and angles are normal and comparable with those found in the related compounds (Ji et al., 2008; He et al.., 2005; Zhen et al., 2005; Zhang et al.., 2007). The dihedral angle between the two benzene rings is 23.5 (6)°.

In the crystal structure, intermolecular N—H—O hydrogen bonds (Table 1) link molecules into chains running along the a axis (Fig. 2).

Related literature top

For general background to the applications of Schiff bases in the pharmaceutical and agrochemical fields, see: Bernardino et al. (2006); Zhang et al. (2008). For related structures, see: Ji & Shi (2008); He & Liu (2005); Zhen & Han (2005); Zhang et al. (2007).

Experimental top

The title compound was synthesized by the reaction of benzoylhydrazine (1 mmol, 136.2 mg) with 3-phenyl-propenal (1 mmol, 132.2 mg) in ethanol (20 ml) under reflux conditions (348 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After two days yellow crystals suitable for X-ray diffraction study were obtained. Yield, 222.7 mg, 83%. Analysis calculated for C16H14N2O: C 76.78, H 5.64, N 11.19%; found: C 76.73, H 5.61, N 11.21%.

Refinement top

The H1A atom bonded to N1 was located in a difference map and refined isotropically, other H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms,C—H=0.93, with Uiso(H)=1.2Ueq(C). In the absence of any significant anomalous scatterers in the molecule, the 1215 Friedel pairs were merged before the final refinement.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. A portion of the packing, viewed down the a axis. The dashed lines represent the intermolecular hydrogen bonds.
(E)-N'-[(E)-3-Phenylallylidene]benzohydrazide top
Crystal data top
C16H14N2OF(000) = 528.0
Mr = 250.29Dx = 1.202 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 968 reflections
a = 8.427 (3) Åθ = 0.5–3.2°
b = 10.439 (4) ŵ = 0.08 mm1
c = 15.724 (6) ÅT = 296 K
V = 1383.2 (9) Å3Block, yellow
Z = 40.16 × 0.13 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
1361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 28.2°, θmin = 2.3°
phi and ω scansh = 1111
6868 measured reflectionsk = 1213
1761 independent reflectionsl = 1420
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0355P)2]
where P = (Fo2 + 2Fc2)/3
1761 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.09 e Å3
1 restraintΔρmin = 0.12 e Å3
Crystal data top
C16H14N2OV = 1383.2 (9) Å3
Mr = 250.29Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 8.427 (3) ŵ = 0.08 mm1
b = 10.439 (4) ÅT = 296 K
c = 15.724 (6) Å0.16 × 0.13 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
1361 reflections with I > 2σ(I)
6868 measured reflectionsRint = 0.040
1761 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.09 e Å3
1761 reflectionsΔρmin = 0.12 e Å3
176 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
C11.0668 (3)0.6483 (2)0.48249 (16)0.0652 (6)
C20.9616 (3)0.7307 (2)0.44374 (17)0.0759 (7)
H20.92520.80270.47270.091*
C30.9099 (3)0.7064 (3)0.36146 (18)0.0946 (9)
H30.83730.76120.33570.114*
C40.9659 (4)0.6012 (4)0.3178 (2)0.0980 (9)
H40.93080.58510.26280.118*
C51.0721 (4)0.5212 (3)0.3549 (2)0.0919 (8)
H51.11070.45080.32510.110*
C61.1229 (3)0.5441 (3)0.4371 (2)0.0832 (7)
H61.19570.48890.46220.100*
C71.1258 (3)0.6639 (2)0.57099 (17)0.0686 (6)
C80.9802 (3)0.8064 (2)0.75525 (16)0.0697 (7)
H80.89370.84690.73020.084*
C91.0068 (3)0.8183 (2)0.84500 (16)0.0689 (7)
H91.09720.78080.86800.083*
C100.9088 (3)0.8803 (2)0.89690 (17)0.0720 (7)
H100.82520.92350.87100.086*
C110.9157 (3)0.8892 (2)0.98938 (17)0.0670 (6)
C121.0264 (3)0.8252 (3)1.03800 (18)0.0859 (8)
H121.10260.77501.01120.103*
C131.0268 (4)0.8341 (3)1.1250 (2)0.1066 (10)
H131.10250.78991.15650.128*
C140.9169 (5)0.9073 (3)1.1655 (2)0.1060 (11)
H140.91700.91301.22450.127*
C150.8062 (4)0.9724 (3)1.1190 (2)0.1051 (11)
H150.73151.02331.14650.126*
C160.8049 (3)0.9630 (2)1.03158 (18)0.0849 (8)
H160.72841.00701.00060.102*
H1A0.938 (3)0.761 (2)0.6107 (14)0.062 (7)*
N11.0322 (3)0.7305 (2)0.62472 (13)0.0713 (6)
N21.0757 (2)0.7398 (2)0.70954 (13)0.0714 (6)
O11.25170 (19)0.61572 (17)0.59406 (13)0.0867 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0605 (13)0.0711 (14)0.0640 (16)0.0100 (13)0.0033 (13)0.0047 (13)
C20.0778 (15)0.0902 (17)0.0597 (16)0.0012 (13)0.0077 (16)0.0089 (15)
C30.094 (2)0.125 (2)0.064 (2)0.0053 (19)0.0004 (17)0.0212 (19)
C40.108 (2)0.125 (2)0.0611 (19)0.021 (2)0.0000 (18)0.0016 (19)
C50.107 (2)0.0881 (18)0.080 (2)0.0092 (18)0.0003 (17)0.0115 (18)
C60.0847 (16)0.0818 (16)0.083 (2)0.0035 (14)0.0061 (17)0.0025 (16)
C70.0635 (14)0.0725 (15)0.0697 (18)0.0098 (13)0.0013 (14)0.0004 (14)
C80.0603 (14)0.0779 (17)0.0708 (18)0.0045 (13)0.0098 (14)0.0068 (14)
C90.0631 (14)0.0798 (17)0.0639 (17)0.0003 (13)0.0082 (13)0.0039 (13)
C100.0632 (15)0.0773 (16)0.0756 (18)0.0023 (14)0.0107 (14)0.0051 (14)
C110.0671 (14)0.0620 (13)0.0718 (18)0.0046 (13)0.0022 (15)0.0013 (12)
C120.0867 (18)0.0919 (18)0.079 (2)0.0115 (17)0.0065 (16)0.0057 (18)
C130.139 (3)0.106 (2)0.075 (2)0.012 (2)0.015 (2)0.011 (2)
C140.166 (3)0.0823 (19)0.069 (2)0.018 (2)0.009 (2)0.0045 (17)
C150.138 (3)0.081 (2)0.097 (3)0.000 (2)0.030 (2)0.0086 (18)
C160.0878 (19)0.0784 (16)0.088 (2)0.0029 (16)0.0050 (16)0.0050 (15)
N10.0655 (13)0.0850 (15)0.0634 (15)0.0003 (12)0.0073 (13)0.0041 (12)
N20.0702 (12)0.0839 (13)0.0601 (14)0.0021 (11)0.0045 (11)0.0042 (10)
O10.0694 (10)0.1060 (12)0.0847 (13)0.0098 (10)0.0118 (10)0.0070 (10)
Geometric parameters (Å, º) top
C1—C21.378 (3)C9—C101.330 (3)
C1—C61.384 (3)C9—H90.9300
C1—C71.486 (3)C10—C111.458 (3)
C2—C31.389 (4)C10—H100.9300
C2—H20.9300C11—C121.379 (4)
C3—C41.378 (4)C11—C161.380 (4)
C3—H30.9300C12—C131.371 (4)
C4—C51.356 (4)C12—H120.9300
C4—H40.9300C13—C141.359 (5)
C5—C61.382 (4)C13—H130.9300
C5—H50.9300C14—C151.366 (4)
C6—H60.9300C14—H140.9300
C7—O11.229 (3)C15—C161.378 (4)
C7—N11.349 (3)C15—H150.9300
C8—N21.284 (3)C16—H160.9300
C8—C91.434 (3)N1—N21.386 (3)
C8—H80.9300N1—H1A0.88 (2)
C2—C1—C6118.9 (3)C8—C9—H9118.4
C2—C1—C7124.1 (2)C9—C10—C11128.2 (2)
C6—C1—C7117.0 (2)C9—C10—H10115.9
C1—C2—C3120.0 (3)C11—C10—H10115.9
C1—C2—H2120.0C12—C11—C16117.5 (3)
C3—C2—H2120.0C12—C11—C10123.3 (3)
C4—C3—C2120.2 (3)C16—C11—C10119.2 (3)
C4—C3—H3119.9C13—C12—C11121.5 (3)
C2—C3—H3119.9C13—C12—H12119.3
C5—C4—C3120.2 (3)C11—C12—H12119.3
C5—C4—H4119.9C14—C13—C12120.2 (3)
C3—C4—H4119.9C14—C13—H13119.9
C4—C5—C6120.0 (3)C12—C13—H13119.9
C4—C5—H5120.0C13—C14—C15119.7 (3)
C6—C5—H5120.0C13—C14—H14120.2
C5—C6—C1120.8 (3)C15—C14—H14120.2
C5—C6—H6119.6C14—C15—C16120.2 (3)
C1—C6—H6119.6C14—C15—H15119.9
O1—C7—N1122.1 (2)C16—C15—H15119.9
O1—C7—C1121.3 (2)C15—C16—C11120.9 (3)
N1—C7—C1116.6 (2)C15—C16—H16119.5
N2—C8—C9120.0 (2)C11—C16—H16119.5
N2—C8—H8120.0C7—N1—N2119.0 (2)
C9—C8—H8120.0C7—N1—H1A123.6 (15)
C10—C9—C8123.3 (2)N2—N1—H1A116.9 (15)
C10—C9—H9118.4C8—N2—N1114.3 (2)
C6—C1—C2—C32.0 (3)C9—C10—C11—C123.7 (4)
C7—C1—C2—C3178.3 (2)C9—C10—C11—C16177.5 (2)
C1—C2—C3—C41.2 (4)C16—C11—C12—C130.2 (4)
C2—C3—C4—C50.2 (4)C10—C11—C12—C13178.7 (3)
C3—C4—C5—C60.8 (4)C11—C12—C13—C140.2 (5)
C4—C5—C6—C10.0 (4)C12—C13—C14—C150.2 (5)
C2—C1—C6—C51.4 (3)C13—C14—C15—C160.7 (5)
C7—C1—C6—C5178.8 (2)C14—C15—C16—C110.7 (5)
C2—C1—C7—O1156.8 (2)C12—C11—C16—C150.3 (4)
C6—C1—C7—O123.0 (3)C10—C11—C16—C15179.1 (2)
C2—C1—C7—N124.8 (3)O1—C7—N1—N23.2 (3)
C6—C1—C7—N1155.5 (2)C1—C7—N1—N2175.23 (19)
N2—C8—C9—C10176.6 (2)C9—C8—N2—N1176.9 (2)
C8—C9—C10—C11174.1 (2)C7—N1—N2—C8179.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.88 (2)2.05 (2)2.898 (3)161 (2)
Symmetry code: (i) x1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC16H14N2O
Mr250.29
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)296
a, b, c (Å)8.427 (3), 10.439 (4), 15.724 (6)
V3)1383.2 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.16 × 0.13 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6868, 1761, 1361
Rint0.040
(sin θ/λ)max1)0.664
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.096, 1.01
No. of reflections1761
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.09, 0.12

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.88 (2)2.05 (2)2.898 (3)161 (2)
Symmetry code: (i) x1/2, y+3/2, z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (30940094) and the Science Foundation for Excellent Youth Scholars of the Education Commission of Hunan Province, China (10B077).

References

First citationBernardino, A. M. R., Gomes, A. O., Charret, K. S., Freita, A. C. C., Machado, G. M. C., Canto-Cavalheiro, M. M., Leon, L. L. & Amaral, V. F. (2006). Eur. J. Med. Chem. 41, 80–87.  Web of Science CrossRef PubMed CAS
First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHe, Y.-Z. & Liu, D.-Z. (2005). Acta Cryst. E61, o3855–o3856.  Web of Science CSD CrossRef IUCr Journals
First citationJi, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o1918.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationZhang, H. Q., Li, J. Z., Zhang, Y. & Zhang, D. (2008). Chin. J. Inorg. Chem. 24, 990–993.  Web of Science CSD CrossRef CAS
First citationZhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536.  Web of Science CSD CrossRef IUCr Journals
First citationZhen, X.-L. & Han, J.-R. (2005). Acta Cryst. E61, o4360–o4361.  Web of Science CSD CrossRef IUCr Journals

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