(Z)-4-(2-Hy-droxy-anilino)pent-3-en-2-one.

In the title compound, C(11)H(13)NO(2), the dihedral angle between the planes defined by the 2-hy-droxy-phenyl-amino group and the pent-3-en-2-one mean plane [maximum deviations = 0.0275 (19) and 0.054 (2) Å, respectively] is 31.01 (10)°. There are intra-molecular bifurcated N-H⋯(O,O) hydrogen bonds involving the amine NH group and the adjacent carbonyl and hy-droxy O atoms. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For transition metal complexes of Schiff bases, see: Salavati-Niasari (2006 ▶); Xiong et al. (2007 ▶); Basu et al. (2010 ▶). For the biological activity of Schiff bases, see: Jarrahpour et al. (2007 ▶); El-Masry et al. (2000 ▶); Singh & Dash (1988 ▶). For the use of Schiff bases as inter­midiates in many industrial processes, see: Salavati-Niasari & Nezamoddin Mirsattari (2007 ▶); Katsuki (1995 ▶); Ahamad et al. (2010 ▶); Da Silva et al. (2010 ▶); Soltani et al. (2010 ▶). For the tautomeric properties and conformations of the title compound, see: Kabak et al. (1998 ▶). For the photoconductivity of the title compound, see: Parekh et al. (2007 ▶), and for its thermochromic properties, see: Moustakali-Mavridis et al. (1978 ▶); Hadjoudis et al. (1987 ▶). For hydrogen bonding and graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H13NO2

M = 191.22

Orthorhombic,

a = 8.7826 (4) Å

b = 10.3999 (5) Å

c = 11.1827 (3) Å

V = 1021.41 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.50 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

7005 measured reflections

1359 independent reflections

1260 reflections with I > 2σ(I)

R int = 0.105

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.07

1359 reflections

137 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027894/su2455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027894/su2455Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027894/su2455Isup3.cml

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

C11H13NO2	F(000) = 408
Mr = 191.22	Dx = 1.244 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4219 reflections
a = 8.7826 (4) Å	θ = 1.0–27.5°
b = 10.3999 (5) Å	µ = 0.09 mm−1
c = 11.1827 (3) Å	T = 173 K
V = 1021.41 (7) Å3	Prism, yellow
Z = 4	0.50 × 0.30 × 0.20 mm

Nonius KappaCCD diffractometer	1260 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.105
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
phi and ω scans	h = −10→11
7005 measured reflections	k = −12→13
1359 independent reflections	l = −14→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0792P)2 + 0.0946P] where P = (Fo2 + 2Fc2)/3
1359 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.58388 (17)	0.70724 (15)	0.03852 (14)	0.0320 (4)
O2	0.95582 (17)	0.68677 (15)	0.15060 (12)	0.0331 (4)
N1	0.69854 (19)	0.57884 (17)	0.22040 (14)	0.0248 (4)
C1	0.4942 (2)	0.61181 (19)	0.08258 (17)	0.0257 (5)
C2	0.3527 (2)	0.5805 (2)	0.03503 (19)	0.0322 (6)
C3	0.2679 (3)	0.4816 (2)	0.0850 (2)	0.0387 (7)
C4	0.3242 (3)	0.4126 (2)	0.1812 (2)	0.0402 (7)
C5	0.4665 (3)	0.4415 (2)	0.2282 (2)	0.0349 (6)
C6	0.5510 (2)	0.54332 (18)	0.18138 (17)	0.0256 (5)
C7	0.7611 (2)	0.57778 (19)	0.33025 (16)	0.0253 (5)
C8	0.6698 (3)	0.5315 (3)	0.43570 (18)	0.0392 (7)
C9	0.9069 (2)	0.6227 (2)	0.34810 (17)	0.0276 (5)
C10	0.9993 (2)	0.6778 (2)	0.25800 (17)	0.0275 (5)
C11	1.1530 (3)	0.7300 (3)	0.2911 (2)	0.0400 (7)
H1	0.542 (3)	0.738 (3)	−0.032 (3)	0.044 (7)*
H1N	0.762 (3)	0.619 (3)	0.162 (2)	0.033 (6)*
H2	0.31400	0.62690	−0.03160	0.0390*
H3	0.17070	0.46110	0.05310	0.0460*
H4	0.26530	0.34520	0.21510	0.0480*
H5	0.50630	0.39190	0.29240	0.0420*
H8A	0.56570	0.56470	0.42990	0.0590*
H8B	0.71680	0.56240	0.50980	0.0590*
H8C	0.66760	0.43730	0.43600	0.0590*
H9	0.94840	0.61620	0.42630	0.0330*
H11A	1.23200	0.68290	0.24730	0.0600*
H11B	1.16920	0.71960	0.37730	0.0600*
H11C	1.15810	0.82140	0.27030	0.0600*

	U11	U22	U33	U12	U13	U23
O1	0.0344 (8)	0.0336 (8)	0.0281 (7)	−0.0051 (7)	−0.0054 (6)	0.0101 (6)
O2	0.0357 (7)	0.0395 (8)	0.0241 (7)	−0.0059 (7)	0.0004 (6)	0.0062 (6)
N1	0.0271 (8)	0.0257 (8)	0.0217 (7)	−0.0021 (7)	0.0009 (6)	0.0040 (6)
C1	0.0274 (9)	0.0234 (9)	0.0263 (9)	0.0023 (8)	0.0021 (8)	0.0009 (7)
C2	0.0305 (10)	0.0324 (10)	0.0336 (10)	0.0031 (10)	−0.0033 (8)	−0.0031 (9)
C3	0.0308 (10)	0.0342 (11)	0.0511 (13)	−0.0023 (10)	−0.0051 (10)	−0.0075 (10)
C4	0.0403 (12)	0.0300 (11)	0.0503 (14)	−0.0086 (11)	−0.0004 (10)	0.0027 (10)
C5	0.0407 (12)	0.0263 (10)	0.0377 (11)	−0.0044 (10)	−0.0006 (9)	0.0057 (8)
C6	0.0271 (9)	0.0236 (9)	0.0261 (9)	0.0004 (8)	−0.0002 (7)	−0.0003 (7)
C7	0.0319 (9)	0.0236 (8)	0.0205 (9)	0.0043 (8)	0.0006 (7)	0.0043 (7)
C8	0.0406 (12)	0.0513 (13)	0.0258 (10)	−0.0059 (12)	0.0040 (9)	0.0093 (10)
C9	0.0324 (10)	0.0281 (10)	0.0223 (8)	0.0029 (9)	−0.0028 (8)	0.0042 (7)
C10	0.0304 (9)	0.0250 (9)	0.0272 (9)	0.0023 (9)	0.0004 (7)	−0.0007 (7)
C11	0.0374 (11)	0.0434 (13)	0.0393 (11)	−0.0088 (12)	−0.0011 (10)	−0.0005 (10)

O1—C1	1.359 (2)	C9—C10	1.415 (3)
O2—C10	1.264 (2)	C10—C11	1.501 (3)
O1—H1	0.93 (3)	C2—H2	0.9500
N1—C6	1.416 (2)	C3—H3	0.9500
N1—C7	1.346 (2)	C4—H4	0.9500
N1—H1N	0.96 (3)	C5—H5	0.9500
C1—C2	1.390 (3)	C8—H8A	0.9800
C1—C6	1.406 (3)	C8—H8B	0.9800
C2—C3	1.387 (3)	C8—H8C	0.9800
C3—C4	1.385 (3)	C9—H9	0.9500
C4—C5	1.389 (4)	C11—H11A	0.9800
C5—C6	1.395 (3)	C11—H11B	0.9800
C7—C8	1.505 (3)	C11—H11C	0.9800
C7—C9	1.378 (3)
C1—O1—H1	109.3 (18)	C3—C2—H2	120.00
C6—N1—C7	130.74 (16)	C2—C3—H3	120.00
C6—N1—H1N	115.9 (15)	C4—C3—H3	120.00
C7—N1—H1N	112.9 (15)	C3—C4—H4	120.00
O1—C1—C2	123.38 (18)	C5—C4—H4	120.00
O1—C1—C6	116.69 (16)	C4—C5—H5	120.00
C2—C1—C6	119.93 (18)	C6—C5—H5	120.00
C1—C2—C3	120.0 (2)	C7—C8—H8A	109.00
C2—C3—C4	120.4 (2)	C7—C8—H8B	109.00
C3—C4—C5	120.2 (2)	C7—C8—H8C	109.00
C4—C5—C6	120.1 (2)	H8A—C8—H8B	109.00
N1—C6—C1	115.76 (16)	H8A—C8—H8C	110.00
N1—C6—C5	124.68 (18)	H8B—C8—H8C	109.00
C1—C6—C5	119.39 (18)	C7—C9—H9	118.00
C8—C7—C9	119.35 (17)	C10—C9—H9	118.00
N1—C7—C8	120.02 (17)	C10—C11—H11A	109.00
N1—C7—C9	120.60 (17)	C10—C11—H11B	109.00
C7—C9—C10	124.56 (17)	C10—C11—H11C	109.00
O2—C10—C9	122.23 (17)	H11A—C11—H11B	109.00
O2—C10—C11	118.64 (18)	H11A—C11—H11C	110.00
C9—C10—C11	119.12 (17)	H11B—C11—H11C	110.00
C1—C2—H2	120.00
C6—N1—C7—C9	−177.06 (19)	C1—C2—C3—C4	−0.8 (3)
C7—N1—C6—C1	148.6 (2)	C2—C3—C4—C5	−0.3 (3)
C7—N1—C6—C5	−36.2 (3)	C3—C4—C5—C6	2.3 (3)
C6—N1—C7—C8	0.8 (3)	C4—C5—C6—N1	−178.26 (19)
C6—C1—C2—C3	−0.1 (3)	C4—C5—C6—C1	−3.2 (3)
O1—C1—C6—N1	−2.5 (3)	N1—C7—C9—C10	3.0 (3)
O1—C1—C6—C5	−177.92 (18)	C8—C7—C9—C10	−174.9 (2)
O1—C1—C2—C3	179.93 (18)	C7—C9—C10—O2	−2.2 (3)
C2—C1—C6—N1	177.60 (17)	C7—C9—C10—C11	176.5 (2)
C2—C1—C6—C5	2.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.96 (3)	2.28 (3)	2.633 (2)	100.9 (18)
N1—H1N···O2	0.96 (3)	1.85 (3)	2.641 (2)	139 (2)
O1—H1···O2i	0.93 (3)	1.72 (3)	2.637 (2)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.96 (3)	2.28 (3)	2.633 (2)	100.9 (18)
N1—H1N⋯O2	0.96 (3)	1.85 (3)	2.641 (2)	139 (2)
O1—H1⋯O2i	0.93 (3)	1.72 (3)	2.637 (2)	172 (3)

Symmetry code: (i) .