(E)-N'-[(E)-3-Phenyl-allyl-idene]benzo-hydrazide.

In the title mol-ecule, C(16)H(14)N(2)O, the dihedral angle between the two phenyl rings is 23.5 (6)°. In the crystal, N-H-O hydrogen bonds link mol-ecules 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 = 250.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 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

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053645/cv5216sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811053645/cv5216Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14N2O	F(000) = 528.0
Mr = 250.29	Dx = 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

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

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(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
1761 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.09 e Å−3
1 restraint	Δρmin = −0.12 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) .