(2E)-N'-[(E)-2-Hy-droxy-benzyl-idene]-3-phenyl-prop-2-enohydrazide.

In the non-planar title compound, C(16)H(14)N(2)O(2), the dihedral angle between the phenyl rings is 16.67 (8)°. An E conformation is found for each of the imine [1.286 (2) Å] and ethyl-ene [1.335 (2) Å] bonds. The amide O and H atoms are anti, and an intra-molecular hy-droxy O-H⋯N hydrogen bond is noted. The formation of N-H⋯O(hy-droxy) hydrogen bonds in the crystal packing leads to helical chains along the b axis. Supra-molecular layers in the ab plane are formed as the chains are linked by C-H⋯O inter-actions.

Related literature

For background to the biological activity of compounds with the N-acyl­hydrazone framework, (E)-cinnamoylhydrazone derivatives, and related structures, see: Carvalho et al. (2012a ▶). For the synthesis, see: Carvalho et al. (2012b ▶). For background to the data collection at the National Crystallographic Service, see: Coles & Gale (2012 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Orthorhombic,

a = 24.2707 (17) Å

b = 5.1322 (2) Å

c = 10.5192 (4) Å

V = 1310.29 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.19 × 0.09 × 0.03 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2011 ▶) T min = 0.878, T max = 1.000

5871 measured reflections

1575 independent reflections

1504 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 0.93

1575 reflections

181 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2011 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028516/hb6860sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028516/hb6860Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028516/hb6860Isup3.cml

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

C16H14N2O2	F(000) = 560
Mr = 266.29	Dx = 1.350 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5659 reflections
a = 24.2707 (17) Å	θ = 3.4–27.5°
b = 5.1322 (2) Å	µ = 0.09 mm−1
c = 10.5192 (4) Å	T = 100 K
V = 1310.29 (12) Å3	Plate, colourless
Z = 4	0.19 × 0.09 × 0.03 mm

Rigaku Saturn724+ diffractometer	1575 independent reflections
Radiation source: Rotating Anode	1504 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.022
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.4°
profile data from ω–scans	h = −30→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2011)	k = −6→6
Tmin = 0.878, Tmax = 1.000	l = −13→13
5871 measured reflections

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3579P] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
1575 reflections	Δρmax = 0.20 e Å−3
181 parameters	Δρmin = −0.15 e Å−3
1 restraint	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.69975 (5)	0.5777 (2)	−0.10431 (12)	0.0192 (3)
H1O	0.7247 (7)	0.671 (4)	−0.071 (2)	0.029*
O2	0.81273 (5)	1.1490 (3)	−0.06463 (13)	0.0232 (3)
N1	0.75962 (6)	0.7782 (3)	0.07685 (14)	0.0150 (3)
N2	0.79692 (6)	0.9517 (3)	0.12637 (14)	0.0158 (3)
H2N	0.7997 (9)	0.959 (4)	0.2096 (10)	0.019*
C1	0.67996 (7)	0.4128 (3)	−0.01381 (17)	0.0157 (3)
C2	0.69722 (7)	0.4288 (3)	0.11420 (17)	0.0140 (3)
C3	0.67560 (7)	0.2498 (3)	0.20137 (17)	0.0171 (4)
H3	0.6869	0.2577	0.2877	0.021*
C4	0.63806 (7)	0.0613 (3)	0.16428 (19)	0.0187 (4)
H4	0.6241	−0.0602	0.2244	0.022*
C5	0.62097 (7)	0.0517 (3)	0.03833 (19)	0.0201 (4)
H5	0.5947	−0.0753	0.0128	0.024*
C6	0.64170 (7)	0.2249 (3)	−0.05053 (18)	0.0197 (4)
H6	0.6298	0.2157	−0.1365	0.024*
C7	0.73698 (7)	0.6215 (3)	0.15666 (17)	0.0150 (3)
H7	0.7463	0.6319	0.2442	0.018*
C8	0.82227 (7)	1.1293 (3)	0.04921 (17)	0.0156 (3)
C9	0.86435 (7)	1.2853 (3)	0.11785 (17)	0.0161 (3)
H9	0.8711	1.2542	0.2055	0.019*
C10	0.89272 (7)	1.4693 (3)	0.05648 (17)	0.0170 (3)
H10	0.8815	1.5065	−0.0281	0.020*
C11	0.93932 (7)	1.6197 (3)	0.10555 (17)	0.0159 (3)
C12	0.96062 (7)	1.8241 (3)	0.03252 (19)	0.0203 (4)
H12	0.9442	1.8652	−0.0469	0.024*
C13	1.00558 (8)	1.9677 (4)	0.0748 (2)	0.0226 (4)
H13	1.0196	2.1061	0.0242	0.027*
C14	1.03004 (7)	1.9097 (4)	0.19034 (19)	0.0225 (4)
H14	1.0606	2.0087	0.2193	0.027*
C15	1.00967 (7)	1.7064 (4)	0.26359 (18)	0.0210 (4)
H15	1.0266	1.6658	0.3426	0.025*
C16	0.96482 (7)	1.5624 (3)	0.22228 (18)	0.0177 (3)
H16	0.9512	1.4238	0.2732	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0245 (6)	0.0213 (6)	0.0118 (6)	−0.0067 (5)	−0.0012 (5)	−0.0003 (5)
O2	0.0293 (7)	0.0274 (7)	0.0130 (6)	−0.0075 (5)	−0.0028 (6)	−0.0001 (6)
N1	0.0147 (6)	0.0154 (6)	0.0149 (6)	−0.0003 (5)	−0.0009 (5)	−0.0031 (6)
N2	0.0175 (7)	0.0183 (7)	0.0115 (7)	−0.0035 (5)	−0.0015 (6)	−0.0028 (6)
C1	0.0148 (7)	0.0167 (7)	0.0154 (8)	0.0021 (6)	0.0008 (6)	−0.0019 (7)
C2	0.0136 (7)	0.0144 (7)	0.0141 (8)	0.0011 (6)	0.0011 (6)	−0.0023 (7)
C3	0.0170 (8)	0.0190 (8)	0.0154 (9)	0.0017 (6)	0.0011 (7)	−0.0009 (7)
C4	0.0189 (8)	0.0156 (8)	0.0215 (9)	−0.0003 (6)	0.0054 (7)	0.0021 (7)
C5	0.0175 (8)	0.0179 (8)	0.0248 (9)	−0.0029 (6)	0.0001 (7)	−0.0049 (7)
C6	0.0189 (8)	0.0225 (8)	0.0177 (8)	−0.0014 (7)	−0.0032 (7)	−0.0041 (8)
C7	0.0150 (7)	0.0182 (8)	0.0118 (7)	0.0005 (6)	−0.0007 (6)	−0.0029 (7)
C8	0.0159 (7)	0.0166 (8)	0.0143 (8)	0.0010 (6)	0.0009 (6)	−0.0013 (7)
C9	0.0167 (7)	0.0174 (8)	0.0141 (7)	0.0008 (6)	−0.0010 (6)	−0.0024 (7)
C10	0.0175 (8)	0.0176 (8)	0.0158 (8)	0.0015 (6)	−0.0009 (7)	−0.0018 (7)
C11	0.0148 (7)	0.0148 (7)	0.0180 (8)	0.0017 (6)	0.0028 (7)	−0.0019 (7)
C12	0.0212 (8)	0.0180 (8)	0.0217 (9)	0.0004 (6)	0.0004 (7)	0.0039 (7)
C13	0.0207 (9)	0.0160 (8)	0.0312 (10)	−0.0016 (6)	0.0038 (8)	0.0015 (8)
C14	0.0175 (8)	0.0189 (8)	0.0311 (11)	−0.0004 (7)	0.0009 (7)	−0.0060 (8)
C15	0.0178 (8)	0.0230 (9)	0.0223 (9)	0.0025 (7)	−0.0015 (7)	−0.0046 (8)
C16	0.0173 (7)	0.0174 (8)	0.0182 (8)	0.0010 (6)	0.0030 (7)	−0.0001 (7)

O1—C1	1.361 (2)	C7—H7	0.9500
O1—H1O	0.848 (10)	C8—C9	1.485 (2)
O2—C8	1.224 (2)	C9—C10	1.335 (2)
N1—C7	1.286 (2)	C9—H9	0.9500
N1—N2	1.3727 (19)	C10—C11	1.463 (2)
N2—C8	1.367 (2)	C10—H10	0.9500
N2—H2N	0.879 (10)	C11—C12	1.399 (2)
C1—C6	1.393 (2)	C11—C16	1.406 (2)
C1—C2	1.413 (3)	C12—C13	1.390 (3)
C2—C3	1.400 (2)	C12—H12	0.9500
C2—C7	1.452 (2)	C13—C14	1.385 (3)
C3—C4	1.385 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.388 (3)
C4—C5	1.389 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.386 (2)
C5—C6	1.385 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500
C1—O1—H1O	108.1 (18)	O2—C8—C9	124.15 (16)
C7—N1—N2	116.09 (15)	N2—C8—C9	112.36 (15)
C8—N2—N1	120.28 (15)	C10—C9—C8	120.06 (16)
C8—N2—H2N	122.0 (15)	C10—C9—H9	120.0
N1—N2—H2N	117.1 (15)	C8—C9—H9	120.0
O1—C1—C6	118.13 (17)	C9—C10—C11	126.95 (16)
O1—C1—C2	121.73 (15)	C9—C10—H10	116.5
C6—C1—C2	120.14 (17)	C11—C10—H10	116.5
C3—C2—C1	118.36 (15)	C12—C11—C16	118.26 (16)
C3—C2—C7	119.64 (16)	C12—C11—C10	119.17 (16)
C1—C2—C7	121.99 (16)	C16—C11—C10	122.55 (16)
C4—C3—C2	121.36 (17)	C13—C12—C11	120.80 (18)
C4—C3—H3	119.3	C13—C12—H12	119.6
C2—C3—H3	119.3	C11—C12—H12	119.6
C3—C4—C5	119.33 (17)	C14—C13—C12	120.23 (18)
C3—C4—H4	120.3	C14—C13—H13	119.9
C5—C4—H4	120.3	C12—C13—H13	119.9
C6—C5—C4	120.84 (17)	C13—C14—C15	119.73 (17)
C6—C5—H5	119.6	C13—C14—H14	120.1
C4—C5—H5	119.6	C15—C14—H14	120.1
C5—C6—C1	119.96 (17)	C16—C15—C14	120.44 (17)
C5—C6—H6	120.0	C16—C15—H15	119.8
C1—C6—H6	120.0	C14—C15—H15	119.8
N1—C7—C2	120.60 (16)	C15—C16—C11	120.54 (17)
N1—C7—H7	119.7	C15—C16—H16	119.7
C2—C7—H7	119.7	C11—C16—H16	119.7
O2—C8—N2	123.43 (16)
C7—N1—N2—C8	−178.71 (15)	N1—N2—C8—O2	1.8 (3)
O1—C1—C2—C3	−179.07 (15)	N1—N2—C8—C9	−175.41 (14)
C6—C1—C2—C3	1.0 (2)	O2—C8—C9—C10	3.3 (3)
O1—C1—C2—C7	0.0 (2)	N2—C8—C9—C10	−179.52 (15)
C6—C1—C2—C7	−179.97 (16)	C8—C9—C10—C11	−172.84 (16)
C1—C2—C3—C4	−0.2 (2)	C9—C10—C11—C12	−173.45 (17)
C7—C2—C3—C4	−179.29 (15)	C9—C10—C11—C16	8.4 (3)
C2—C3—C4—C5	−0.8 (3)	C16—C11—C12—C13	−0.4 (3)
C3—C4—C5—C6	1.1 (3)	C10—C11—C12—C13	−178.64 (16)
C4—C5—C6—C1	−0.4 (3)	C11—C12—C13—C14	0.1 (3)
O1—C1—C6—C5	179.34 (15)	C12—C13—C14—C15	0.4 (3)
C2—C1—C6—C5	−0.7 (3)	C13—C14—C15—C16	−0.4 (3)
N2—N1—C7—C2	−179.55 (14)	C14—C15—C16—C11	0.1 (3)
C3—C2—C7—N1	176.11 (15)	C12—C11—C16—C15	0.3 (2)
C1—C2—C7—N1	−2.9 (2)	C10—C11—C16—C15	178.50 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (2)	1.86 (2)	2.6080 (19)	147 (2)
N2—H2n···O1i	0.88 (1)	2.05 (1)	2.9070 (19)	165 (2)
C3—H3···O2ii	0.95	2.54	3.215 (2)	128
C7—H7···O2ii	0.95	2.47	3.174 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (2)	1.86 (2)	2.6080 (19)	147 (2)
N2—H2n⋯O1i	0.88 (1)	2.05 (1)	2.9070 (19)	165 (2)
C3—H3⋯O2ii	0.95	2.54	3.215 (2)	128
C7—H7⋯O2ii	0.95	2.47	3.174 (2)	131

Symmetry codes: (i) ; (ii) .