2-Hydr-oxy-N'-[(1E,2E)-3-phenyl-prop-2-enyl-idene]benzohydrazide.

In mol-ecule of the title compound, C(16)H(14)N(2)O(2), the two aromatic rings form a dihedral angle of 6.93 (3)° and an intramolecular N-H⋯O hydrogen bond occurs. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running in the [10] direction.

Related literature

For the coordination chemistry of Schiff bases, see: Garnovskii et al. (1993 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶); Shi et al. (2007 ▶). For Schiff bases and biological systems, see: Anderson et al. (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Monoclinic,

a = 4.8892 (6) Å

b = 26.563 (3) Å

c = 10.7367 (13) Å

β = 102.305 (2)°

V = 1362.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.987, T max = 0.991

7141 measured reflections

2395 independent reflections

1354 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.05

2395 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028481/cv2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028481/cv2440Isup2.hkl

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

C16H14N2O2	F(000) = 560
Mr = 266.29	Dx = 1.298 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 932 reflections
a = 4.8892 (6) Å	θ = 3.6–21.4°
b = 26.563 (3) Å	µ = 0.09 mm−1
c = 10.7367 (13) Å	T = 295 K
β = 102.305 (2)°	Block, colourless
V = 1362.4 (3) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2395 independent reflections
Radiation source: fine-focus sealed tube	1354 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.987, Tmax = 0.991	k = −21→31
7141 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.124	w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2395 reflections	Δρmax = 0.14 e Å−3
183 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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
O1	0.5440 (4)	0.26610 (6)	0.08347 (14)	0.0702 (5)
H1	0.6201	0.2633	0.0227	0.105*
O2	0.4213 (4)	0.27755 (6)	0.45173 (13)	0.0687 (5)
N1	0.2766 (4)	0.24015 (6)	0.26236 (15)	0.0508 (5)
H1A	0.2861	0.2378	0.1835	0.061*
N2	0.1041 (4)	0.20892 (7)	0.31262 (16)	0.0513 (5)
C1	0.6656 (4)	0.30391 (8)	0.15959 (19)	0.0483 (6)
C2	0.6118 (4)	0.30864 (8)	0.28157 (18)	0.0450 (5)
C3	0.7379 (5)	0.34777 (9)	0.3569 (2)	0.0634 (7)
H3	0.7048	0.3513	0.4386	0.076*
C4	0.9102 (6)	0.38164 (9)	0.3154 (2)	0.0736 (8)
H4	0.9898	0.4080	0.3676	0.088*
C5	0.9638 (5)	0.37611 (9)	0.1959 (2)	0.0662 (7)
H5	1.0826	0.3986	0.1674	0.079*
C6	0.8438 (5)	0.33774 (9)	0.1184 (2)	0.0606 (7)
H6	0.8818	0.3343	0.0375	0.073*
C7	0.4304 (5)	0.27445 (8)	0.33872 (19)	0.0476 (6)
C8	−0.0380 (5)	0.17709 (8)	0.2358 (2)	0.0529 (6)
H8	−0.0220	0.1766	0.1510	0.064*
C9	−0.2215 (5)	0.14220 (8)	0.2788 (2)	0.0530 (6)
H9	−0.2416	0.1442	0.3628	0.064*
C10	−0.3630 (5)	0.10743 (9)	0.2044 (2)	0.0576 (6)
H10	−0.3419	0.1072	0.1203	0.069*
C11	−0.5490 (5)	0.06929 (8)	0.2383 (2)	0.0529 (6)
C12	−0.6805 (5)	0.03509 (10)	0.1480 (2)	0.0739 (8)
H12	−0.6499	0.0369	0.0655	0.089*
C13	−0.8563 (6)	−0.00161 (11)	0.1777 (3)	0.0842 (9)
H13	−0.9404	−0.0244	0.1156	0.101*
C14	−0.9071 (6)	−0.00457 (10)	0.2973 (3)	0.0761 (8)
H14	−1.0287	−0.0288	0.3169	0.091*
C15	−0.7772 (6)	0.02847 (10)	0.3879 (3)	0.0807 (8)
H15	−0.8084	0.0264	0.4702	0.097*
C16	−0.6002 (5)	0.06496 (9)	0.3590 (2)	0.0670 (7)
H16	−0.5137	0.0871	0.4223	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0858 (13)	0.0893 (13)	0.0482 (9)	−0.0339 (10)	0.0428 (9)	−0.0229 (9)
O2	0.0900 (14)	0.0857 (12)	0.0392 (9)	−0.0137 (9)	0.0337 (8)	−0.0060 (8)
N1	0.0615 (13)	0.0615 (12)	0.0363 (9)	−0.0068 (10)	0.0257 (9)	0.0017 (9)
N2	0.0587 (13)	0.0596 (12)	0.0424 (10)	−0.0030 (10)	0.0263 (9)	0.0069 (9)
C1	0.0531 (15)	0.0568 (14)	0.0384 (12)	−0.0055 (11)	0.0174 (10)	−0.0034 (10)
C2	0.0509 (15)	0.0505 (13)	0.0366 (11)	0.0016 (11)	0.0158 (10)	0.0003 (10)
C3	0.083 (2)	0.0703 (17)	0.0416 (13)	−0.0132 (14)	0.0247 (12)	−0.0088 (12)
C4	0.097 (2)	0.0700 (18)	0.0568 (16)	−0.0233 (15)	0.0219 (15)	−0.0121 (13)
C5	0.0740 (19)	0.0696 (17)	0.0575 (15)	−0.0225 (14)	0.0192 (14)	0.0020 (13)
C6	0.0701 (18)	0.0765 (17)	0.0412 (12)	−0.0134 (13)	0.0252 (12)	0.0026 (12)
C7	0.0552 (15)	0.0547 (14)	0.0383 (12)	0.0047 (11)	0.0218 (11)	0.0002 (11)
C8	0.0614 (17)	0.0631 (15)	0.0377 (12)	−0.0015 (12)	0.0183 (11)	0.0042 (11)
C9	0.0580 (16)	0.0613 (15)	0.0440 (13)	−0.0030 (12)	0.0205 (11)	0.0068 (11)
C10	0.0613 (17)	0.0687 (16)	0.0444 (13)	−0.0007 (13)	0.0151 (12)	0.0044 (12)
C11	0.0528 (16)	0.0563 (15)	0.0501 (14)	0.0024 (12)	0.0118 (11)	0.0029 (12)
C12	0.079 (2)	0.086 (2)	0.0571 (16)	−0.0149 (16)	0.0147 (14)	−0.0071 (14)
C13	0.082 (2)	0.082 (2)	0.085 (2)	−0.0215 (16)	0.0086 (17)	−0.0090 (16)
C14	0.0696 (19)	0.0665 (19)	0.093 (2)	−0.0088 (14)	0.0189 (16)	0.0139 (16)
C15	0.092 (2)	0.082 (2)	0.0768 (18)	−0.0177 (16)	0.0376 (17)	0.0056 (16)
C16	0.076 (2)	0.0684 (17)	0.0609 (16)	−0.0142 (13)	0.0244 (14)	−0.0028 (12)

O1—C1	1.350 (2)	C8—C9	1.433 (3)
O1—H1	0.8200	C8—H8	0.9300
O2—C7	1.226 (2)	C9—C10	1.317 (3)
N1—C7	1.344 (2)	C9—H9	0.9300
N1—N2	1.373 (2)	C10—C11	1.458 (3)
N1—H1A	0.8600	C10—H10	0.9300
N2—C8	1.278 (2)	C11—C16	1.376 (3)
C1—C6	1.388 (3)	C11—C12	1.383 (3)
C1—C2	1.395 (3)	C12—C13	1.381 (3)
C2—C3	1.379 (3)	C12—H12	0.9300
C2—C7	1.490 (3)	C13—C14	1.361 (3)
C3—C4	1.370 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.362 (3)
C4—C5	1.371 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.378 (3)
C5—C6	1.366 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300
C1—O1—H1	109.5	N2—C8—H8	119.6
C7—N1—N2	118.73 (17)	C9—C8—H8	119.6
C7—N1—H1A	120.6	C10—C9—C8	122.9 (2)
N2—N1—H1A	120.6	C10—C9—H9	118.6
C8—N2—N1	116.17 (17)	C8—C9—H9	118.6
O1—C1—C6	120.93 (18)	C9—C10—C11	127.6 (2)
O1—C1—C2	119.23 (18)	C9—C10—H10	116.2
C6—C1—C2	119.8 (2)	C11—C10—H10	116.2
C3—C2—C1	117.9 (2)	C16—C11—C12	117.0 (2)
C3—C2—C7	116.66 (18)	C16—C11—C10	122.8 (2)
C1—C2—C7	125.41 (19)	C12—C11—C10	120.2 (2)
C4—C3—C2	122.2 (2)	C13—C12—C11	121.4 (2)
C4—C3—H3	118.9	C13—C12—H12	119.3
C2—C3—H3	118.9	C11—C12—H12	119.3
C3—C4—C5	119.2 (2)	C14—C13—C12	120.4 (3)
C3—C4—H4	120.4	C14—C13—H13	119.8
C5—C4—H4	120.4	C12—C13—H13	119.8
C6—C5—C4	120.5 (2)	C13—C14—C15	119.0 (3)
C6—C5—H5	119.8	C13—C14—H14	120.5
C4—C5—H5	119.8	C15—C14—H14	120.5
C5—C6—C1	120.4 (2)	C14—C15—C16	120.8 (3)
C5—C6—H6	119.8	C14—C15—H15	119.6
C1—C6—H6	119.8	C16—C15—H15	119.6
O2—C7—N1	121.0 (2)	C11—C16—C15	121.3 (2)
O2—C7—C2	121.1 (2)	C11—C16—H16	119.3
N1—C7—C2	117.84 (17)	C15—C16—H16	119.3
N2—C8—C9	120.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.97	2.6348 (19)	133.
O1—H1···O2i	0.82	2.10	2.804 (3)	144.
O1—H1···N2i	0.82	2.36	3.057 (3)	144.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.97	2.6348 (19)	133
O1—H1⋯O2i	0.82	2.10	2.804 (3)	144

Symmetry code: (i) .