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

Deng, G.-M.; Chen, Z.; Wang, C.-R.; Zhang, H.-M.

doi:10.1107/S1600536811053645

organic compounds

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Volume 68| Part 1| January 2012| Page o160

doi:10.1107/S1600536811053645

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

Gui-Ming Deng,^a,^b Zhen Chen,^b Chao-Run Wang ^b and He-Ming Zhang ^a ^*

^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 ); Zhang et al. (2008 ). For related structures, see: Ji & Shi (2008 ); He & Liu (2005 ); Zhen & Han (2005 ); Zhang et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₄N₂O
M_r = 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)
R_int = 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
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053645/cv5216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053645/cv5216Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053645/cv5216Isup3.cml

checkCIF report

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%.

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

	Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.
	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

C₁₆H₁₄N₂O	F(000) = 528.0
M_r = 250.29	D_x = 1.202 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 968 reflections
a = 8.427 (3) Å	θ = 0.5–3.2°
b = 10.439 (4) Å	µ = 0.08 mm⁻¹
c = 15.724 (6) Å	T = 296 K
V = 1383.2 (9) Å³	Block, yellow
Z = 4	0.16 × 0.13 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	1361 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 28.2°, θ_min = 2.3°
phi and ω scans	h = −11→11
6868 measured reflections	k = −12→13
1761 independent reflections	l = −14→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
1761 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.09 e Å⁻³
1 restraint	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O	V = 1383.2 (9) Å³
M_r = 250.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.427 (3) Å	µ = 0.08 mm⁻¹
b = 10.439 (4) Å	T = 296 K
c = 15.724 (6) Å	0.16 × 0.13 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	1361 reflections with I > 2σ(I)
6868 measured reflections	R_int = 0.040
1761 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.09 e Å⁻³
1761 reflections	Δρ_min = −0.12 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	1.0668 (3)	0.6483 (2)	0.48249 (16)	0.0652 (6)
C2	0.9616 (3)	0.7307 (2)	0.44374 (17)	0.0759 (7)
H2	0.9252	0.8027	0.4727	0.091*
C3	0.9099 (3)	0.7064 (3)	0.36146 (18)	0.0946 (9)
H3	0.8373	0.7612	0.3357	0.114*
C4	0.9659 (4)	0.6012 (4)	0.3178 (2)	0.0980 (9)
H4	0.9308	0.5851	0.2628	0.118*
C5	1.0721 (4)	0.5212 (3)	0.3549 (2)	0.0919 (8)
H5	1.1107	0.4508	0.3251	0.110*
C6	1.1229 (3)	0.5441 (3)	0.4371 (2)	0.0832 (7)
H6	1.1957	0.4889	0.4622	0.100*
C7	1.1258 (3)	0.6639 (2)	0.57099 (17)	0.0686 (6)
C8	0.9802 (3)	0.8064 (2)	0.75525 (16)	0.0697 (7)
H8	0.8937	0.8469	0.7302	0.084*
C9	1.0068 (3)	0.8183 (2)	0.84500 (16)	0.0689 (7)
H9	1.0972	0.7808	0.8680	0.083*
C10	0.9088 (3)	0.8803 (2)	0.89690 (17)	0.0720 (7)
H10	0.8252	0.9235	0.8710	0.086*
C11	0.9157 (3)	0.8892 (2)	0.98938 (17)	0.0670 (6)
C12	1.0264 (3)	0.8252 (3)	1.03800 (18)	0.0859 (8)
H12	1.1026	0.7750	1.0112	0.103*
C13	1.0268 (4)	0.8341 (3)	1.1250 (2)	0.1066 (10)
H13	1.1025	0.7899	1.1565	0.128*
C14	0.9169 (5)	0.9073 (3)	1.1655 (2)	0.1060 (11)
H14	0.9170	0.9130	1.2245	0.127*
C15	0.8062 (4)	0.9724 (3)	1.1190 (2)	0.1051 (11)
H15	0.7315	1.0233	1.1465	0.126*
C16	0.8049 (3)	0.9630 (2)	1.03158 (18)	0.0849 (8)
H16	0.7284	1.0070	1.0006	0.102*
H1A	0.938 (3)	0.761 (2)	0.6107 (14)	0.062 (7)*
N1	1.0322 (3)	0.7305 (2)	0.62472 (13)	0.0713 (6)
N2	1.0757 (2)	0.7398 (2)	0.70954 (13)	0.0714 (6)
O1	1.25170 (19)	0.61572 (17)	0.59406 (13)	0.0867 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0605 (13)	0.0711 (14)	0.0640 (16)	−0.0100 (13)	0.0033 (13)	0.0047 (13)
C2	0.0778 (15)	0.0902 (17)	0.0597 (16)	0.0012 (13)	0.0077 (16)	0.0089 (15)
C3	0.094 (2)	0.125 (2)	0.064 (2)	0.0053 (19)	−0.0004 (17)	0.0212 (19)
C4	0.108 (2)	0.125 (2)	0.0611 (19)	−0.021 (2)	0.0000 (18)	0.0016 (19)
C5	0.107 (2)	0.0881 (18)	0.080 (2)	−0.0092 (18)	−0.0003 (17)	−0.0115 (18)
C6	0.0847 (16)	0.0818 (16)	0.083 (2)	−0.0035 (14)	−0.0061 (17)	−0.0025 (16)
C7	0.0635 (14)	0.0725 (15)	0.0697 (18)	−0.0098 (13)	−0.0013 (14)	0.0004 (14)
C8	0.0603 (14)	0.0779 (17)	0.0708 (18)	−0.0045 (13)	−0.0098 (14)	0.0068 (14)
C9	0.0631 (14)	0.0798 (17)	0.0639 (17)	−0.0003 (13)	−0.0082 (13)	0.0039 (13)
C10	0.0632 (15)	0.0773 (16)	0.0756 (18)	0.0023 (14)	−0.0107 (14)	0.0051 (14)
C11	0.0671 (14)	0.0620 (13)	0.0718 (18)	−0.0046 (13)	−0.0022 (15)	0.0013 (12)
C12	0.0867 (18)	0.0919 (18)	0.079 (2)	0.0115 (17)	−0.0065 (16)	0.0057 (18)
C13	0.139 (3)	0.106 (2)	0.075 (2)	0.012 (2)	−0.015 (2)	0.011 (2)
C14	0.166 (3)	0.0823 (19)	0.069 (2)	−0.018 (2)	0.009 (2)	0.0045 (17)
C15	0.138 (3)	0.081 (2)	0.097 (3)	0.000 (2)	0.030 (2)	−0.0086 (18)
C16	0.0878 (19)	0.0784 (16)	0.088 (2)	0.0029 (16)	0.0050 (16)	−0.0050 (15)
N1	0.0655 (13)	0.0850 (15)	0.0634 (15)	−0.0003 (12)	−0.0073 (13)	0.0041 (12)
N2	0.0702 (12)	0.0839 (13)	0.0601 (14)	−0.0021 (11)	−0.0045 (11)	0.0042 (10)
O1	0.0694 (10)	0.1060 (12)	0.0847 (13)	0.0098 (10)	−0.0118 (10)	−0.0070 (10)

Geometric parameters (Å, º) top

C1—C2	1.378 (3)	C9—C10	1.330 (3)
C1—C6	1.384 (3)	C9—H9	0.9300
C1—C7	1.486 (3)	C10—C11	1.458 (3)
C2—C3	1.389 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.379 (4)
C3—C4	1.378 (4)	C11—C16	1.380 (4)
C3—H3	0.9300	C12—C13	1.371 (4)
C4—C5	1.356 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.359 (5)
C5—C6	1.382 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.366 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—O1	1.229 (3)	C15—C16	1.378 (4)
C7—N1	1.349 (3)	C15—H15	0.9300
C8—N2	1.284 (3)	C16—H16	0.9300
C8—C9	1.434 (3)	N1—N2	1.386 (3)
C8—H8	0.9300	N1—H1A	0.88 (2)

C2—C1—C6	118.9 (3)	C8—C9—H9	118.4
C2—C1—C7	124.1 (2)	C9—C10—C11	128.2 (2)
C6—C1—C7	117.0 (2)	C9—C10—H10	115.9
C1—C2—C3	120.0 (3)	C11—C10—H10	115.9
C1—C2—H2	120.0	C12—C11—C16	117.5 (3)
C3—C2—H2	120.0	C12—C11—C10	123.3 (3)
C4—C3—C2	120.2 (3)	C16—C11—C10	119.2 (3)
C4—C3—H3	119.9	C13—C12—C11	121.5 (3)
C2—C3—H3	119.9	C13—C12—H12	119.3
C5—C4—C3	120.2 (3)	C11—C12—H12	119.3
C5—C4—H4	119.9	C14—C13—C12	120.2 (3)
C3—C4—H4	119.9	C14—C13—H13	119.9
C4—C5—C6	120.0 (3)	C12—C13—H13	119.9
C4—C5—H5	120.0	C13—C14—C15	119.7 (3)
C6—C5—H5	120.0	C13—C14—H14	120.2
C5—C6—C1	120.8 (3)	C15—C14—H14	120.2
C5—C6—H6	119.6	C14—C15—C16	120.2 (3)
C1—C6—H6	119.6	C14—C15—H15	119.9
O1—C7—N1	122.1 (2)	C16—C15—H15	119.9
O1—C7—C1	121.3 (2)	C15—C16—C11	120.9 (3)
N1—C7—C1	116.6 (2)	C15—C16—H16	119.5
N2—C8—C9	120.0 (2)	C11—C16—H16	119.5
N2—C8—H8	120.0	C7—N1—N2	119.0 (2)
C9—C8—H8	120.0	C7—N1—H1A	123.6 (15)
C10—C9—C8	123.3 (2)	N2—N1—H1A	116.9 (15)
C10—C9—H9	118.4	C8—N2—N1	114.3 (2)

C6—C1—C2—C3	2.0 (3)	C9—C10—C11—C12	−3.7 (4)
C7—C1—C2—C3	−178.3 (2)	C9—C10—C11—C16	177.5 (2)
C1—C2—C3—C4	−1.2 (4)	C16—C11—C12—C13	0.2 (4)
C2—C3—C4—C5	−0.2 (4)	C10—C11—C12—C13	−178.7 (3)
C3—C4—C5—C6	0.8 (4)	C11—C12—C13—C14	−0.2 (5)
C4—C5—C6—C1	0.0 (4)	C12—C13—C14—C15	−0.2 (5)
C2—C1—C6—C5	−1.4 (3)	C13—C14—C15—C16	0.7 (5)
C7—C1—C6—C5	178.8 (2)	C14—C15—C16—C11	−0.7 (5)
C2—C1—C7—O1	−156.8 (2)	C12—C11—C16—C15	0.3 (4)
C6—C1—C7—O1	23.0 (3)	C10—C11—C16—C15	179.1 (2)
C2—C1—C7—N1	24.8 (3)	O1—C7—N1—N2	−3.2 (3)
C6—C1—C7—N1	−155.5 (2)	C1—C7—N1—N2	175.23 (19)
N2—C8—C9—C10	−176.6 (2)	C9—C8—N2—N1	176.9 (2)
C8—C9—C10—C11	174.1 (2)	C7—N1—N2—C8	179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.88 (2)	2.05 (2)	2.898 (3)	161 (2)

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O
M_r	250.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	8.427 (3), 10.439 (4), 15.724 (6)
V (Å³)	1383.2 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.16 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6868, 1761, 1361
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.096, 1.01
No. of reflections	1761
No. of parameters	176
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.12

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.88 (2)	2.05 (2)	2.898 (3)	161 (2)

Symmetry code: (i) x−1/2, −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

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