2-[(4-Formyl-phen-yl)(hy-droxy)meth-yl]acrylonitrile.

In the title compound, C(11)H(9)NO(2), the mean planes formed by the phenyl and acryl group are almost orthogonal to each other, with a dihedral angle of 88.61 (7)°. The carbonitrile side chain is almost linear, the C-C-N angle being 179.54 (16)°. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O inter-actions into infinite chains running parallel to the b axis.

Related literature

For uses of acrylonitrile derivatives, see: Ohsumi et al. (1998 ▶). For related structures, see: Cobo et al. (2005 ▶); Nizam Mohideen et al. (2007 ▶).

Experimental

Crystal data

C11H9NO2

M = 187.19

Monoclinic,

a = 7.6089 (5) Å

b = 6.0895 (3) Å

c = 20.5135 (14) Å

β = 93.615 (2)°

V = 948.59 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

12108 measured reflections

2778 independent reflections

2109 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.137

S = 1.04

2778 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102976X/pv2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102976X/pv2428Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102976X/pv2428Isup3.cml

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

C11H9NO2	F(000) = 392
Mr = 187.19	Dx = 1.311 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2778 reflections
a = 7.6089 (5) Å	θ = 2.0–30.1°
b = 6.0895 (3) Å	µ = 0.09 mm−1
c = 20.5135 (14) Å	T = 293 K
β = 93.615 (2)°	Block, colourless
V = 948.59 (10) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 30.1°, θmin = 2.0°
ω scans	h = −10→10
12108 measured reflections	k = −8→5
2778 independent reflections	l = −28→28

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.068P)2 + 0.1498P] where P = (Fo2 + 2Fc2)/3
2778 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 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	0.29788 (17)	1.2762 (2)	0.08969 (7)	0.0530 (3)
H1	0.2060	1.2372	0.1152	0.064*
C2	0.45120 (15)	1.1299 (2)	0.09117 (6)	0.0402 (3)
C3	0.59636 (15)	1.17738 (19)	0.05636 (6)	0.0403 (3)
H3	0.5982	1.3042	0.0312	0.048*
C4	0.73929 (15)	1.03554 (19)	0.05910 (6)	0.0377 (3)
H4	0.8374	1.0683	0.0361	0.045*
C5	0.73630 (14)	0.84482 (18)	0.09612 (5)	0.0341 (2)
C6	0.58917 (16)	0.7961 (2)	0.12973 (6)	0.0440 (3)
H6	0.5855	0.6670	0.1538	0.053*
C7	0.44760 (16)	0.9386 (2)	0.12758 (6)	0.0473 (3)
H7	0.3496	0.9059	0.1507	0.057*
C8	0.88910 (15)	0.68441 (19)	0.09921 (6)	0.0386 (3)
H8	0.8530	0.5530	0.0742	0.046*
C9	0.94025 (16)	0.6160 (2)	0.16879 (6)	0.0416 (3)
C10	0.9246 (2)	0.4136 (2)	0.19036 (8)	0.0658 (4)
H10A	0.9592	0.3799	0.2335	0.079*
H10B	0.8788	0.3045	0.1625	0.079*
C11	1.01071 (18)	0.7847 (2)	0.21163 (7)	0.0499 (3)
N1	1.0657 (2)	0.9196 (3)	0.24571 (8)	0.0783 (4)
O1	0.28115 (14)	1.44271 (18)	0.05813 (6)	0.0647 (3)
O2	1.03273 (12)	0.77961 (17)	0.07008 (5)	0.0550 (3)
H2	1.1103	0.6874	0.0670	0.083*

	U11	U22	U33	U12	U13	U23
C1	0.0386 (6)	0.0578 (8)	0.0626 (8)	0.0154 (6)	0.0044 (6)	−0.0036 (6)
C2	0.0328 (5)	0.0454 (6)	0.0420 (6)	0.0090 (4)	−0.0012 (4)	−0.0055 (5)
C3	0.0394 (6)	0.0378 (6)	0.0434 (6)	0.0073 (4)	−0.0005 (5)	0.0030 (5)
C4	0.0336 (5)	0.0409 (6)	0.0390 (6)	0.0055 (4)	0.0047 (4)	0.0040 (4)
C5	0.0326 (5)	0.0371 (5)	0.0326 (5)	0.0067 (4)	0.0007 (4)	−0.0005 (4)
C6	0.0402 (6)	0.0457 (6)	0.0466 (7)	0.0051 (5)	0.0073 (5)	0.0104 (5)
C7	0.0337 (6)	0.0579 (7)	0.0512 (7)	0.0058 (5)	0.0099 (5)	0.0057 (6)
C8	0.0390 (6)	0.0381 (5)	0.0389 (6)	0.0101 (4)	0.0055 (4)	0.0029 (4)
C9	0.0417 (6)	0.0405 (6)	0.0426 (6)	0.0102 (5)	0.0018 (5)	0.0033 (5)
C10	0.0954 (12)	0.0465 (8)	0.0535 (8)	0.0048 (8)	−0.0100 (8)	0.0109 (6)
C11	0.0546 (7)	0.0469 (7)	0.0476 (7)	0.0105 (6)	−0.0009 (6)	0.0022 (5)
N1	0.0984 (12)	0.0638 (8)	0.0706 (9)	0.0003 (8)	−0.0120 (8)	−0.0121 (7)
O1	0.0556 (6)	0.0605 (6)	0.0781 (7)	0.0279 (5)	0.0057 (5)	0.0043 (5)
O2	0.0419 (5)	0.0599 (6)	0.0653 (6)	0.0204 (4)	0.0195 (4)	0.0194 (5)

C1—O1	1.2055 (18)	C6—H6	0.9300
C1—C2	1.4664 (16)	C7—H7	0.9300
C1—H1	0.9300	C8—O2	1.4036 (15)
C2—C3	1.3829 (17)	C8—C9	1.5139 (16)
C2—C7	1.3853 (18)	C8—H8	0.9800
C3—C4	1.3871 (15)	C9—C10	1.3173 (18)
C3—H3	0.9300	C9—C11	1.4338 (18)
C4—C5	1.3887 (15)	C10—H10A	0.9300
C4—H4	0.9300	C10—H10B	0.9300
C5—C6	1.3835 (16)	C11—N1	1.1410 (19)
C5—C8	1.5168 (14)	O2—H2	0.8200
C6—C7	1.3818 (17)
O1—C1—C2	125.37 (14)	C6—C7—C2	120.24 (11)
O1—C1—H1	117.3	C6—C7—H7	119.9
C2—C1—H1	117.3	C2—C7—H7	119.9
C3—C2—C7	119.84 (10)	O2—C8—C9	110.75 (10)
C3—C2—C1	121.51 (12)	O2—C8—C5	109.36 (9)
C7—C2—C1	118.64 (12)	C9—C8—C5	111.56 (9)
C2—C3—C4	119.92 (11)	O2—C8—H8	108.4
C2—C3—H3	120.0	C9—C8—H8	108.4
C4—C3—H3	120.0	C5—C8—H8	108.4
C3—C4—C5	120.20 (11)	C10—C9—C11	120.17 (13)
C3—C4—H4	119.9	C10—C9—C8	123.43 (12)
C5—C4—H4	119.9	C11—C9—C8	116.39 (11)
C6—C5—C4	119.58 (10)	C9—C10—H10A	120.0
C6—C5—C8	118.90 (10)	C9—C10—H10B	120.0
C4—C5—C8	121.50 (10)	H10A—C10—H10B	120.0
C7—C6—C5	120.20 (11)	N1—C11—C9	179.54 (16)
C7—C6—H6	119.9	C8—O2—H2	109.5
C5—C6—H6	119.9
O1—C1—C2—C3	1.9 (2)	C3—C2—C7—C6	0.60 (19)
O1—C1—C2—C7	−177.02 (14)	C1—C2—C7—C6	179.52 (12)
C7—C2—C3—C4	−1.32 (18)	C6—C5—C8—O2	−171.48 (11)
C1—C2—C3—C4	179.80 (11)	C4—C5—C8—O2	10.23 (15)
C2—C3—C4—C5	0.69 (18)	C6—C5—C8—C9	−48.61 (15)
C3—C4—C5—C6	0.66 (17)	C4—C5—C8—C9	133.09 (11)
C3—C4—C5—C8	178.94 (10)	O2—C8—C9—C10	−122.89 (15)
C4—C5—C6—C7	−1.38 (19)	C5—C8—C9—C10	115.05 (15)
C8—C5—C6—C7	−179.71 (11)	O2—C8—C9—C11	56.40 (14)
C5—C6—C7—C2	0.8 (2)	C5—C8—C9—C11	−65.67 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.99	2.8107 (15)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.99	2.8107 (15)	175

Symmetry code: (i) .