2-[(4-Formyl­phen­yl)(hy­dr­oxy)meth­yl]acrylo­nitrile

In the title compound, C₁₁H₉NO₂, 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, mol­ecules are linked by inter­molecular O—H⋯O inter­actions 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_r = 187.19

• Monoclinic, P 2₁ /n

• a = 7.6089 (5) Å

• b = 6.0895 (3) Å

• c = 20.5135 (14) Å

• β = 93.615 (2)°

• V = 948.59 (10) ų

• 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[F² > 2σ(F²)] = 0.045

• wR(F²) = 0.137

• S = 1.04

• 2778 reflections

• 128 parameters

• H-atom parameters constrained

• Δρ_max = 0.20 e Å⁻³

• Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1^i	0.82	1.99	2.8107 (15)	175
Symmetry code: (i) x+1, y-1, z.

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).

Supporting information

S1. Comment

Acrylonitrile derivatives have been shown to possess antitubercular and antitumour activities (Ohsumi et al., 1998).

In the title compound (Fig. 1), the mean planes formed by the phenyl ring C2—C7 and acryl group (N1/C8—C11) are almost orthogonal to each other with a dihedral angle 88.61 (7)°. The bond length C9—C11 [1.4338 (18) Å] is significantly shorter than the expected value for a C—C single bond because of conjugation effects (Nizam Mohideen et al., 2007). The mean plane of C2—C1—O1 is slightly twisted out of the mean plane of phenyl ring C2—C7 with a dihedral angle 2.62 (9)°. The carbonitrile side chain (C9—C11—N1) is almost linear, with the angle around central carbon atom being 179.54 (16)°. The title compound exhibits structural similarities with closely related structures (Cobo et al.2005, Nizam Mohideen et al.2007).

In the title compound, the crystal packing is stabilized by O2—H2···O1 intermolecular interactions which link the molecules into infinite chains running parallel to the b-axis (Tab. 1 & Fig. 2).

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). For related literature [on what subject?], see: Shi et al. (2002).

S2. Experimental

To a reaction mixture of terephthalaldehyde (1 mmol) and acrylonitrile (2 mmol) was added a catalytic quantity of 1,4-diazabicyclo[2.2.2]octane (10–15 mol %). The reaction mixture was left standing at room temperature in a stoppered sample flask. The progress of the reaction was monitored by Thin Layer Chromatography (TLC) over a period of several days. After 6 days the TLC revealed the presence of a product. The reaction mixture was dissolved in ethyl acetate and washed with aqueous HCl solution (0.25 M) and water followed by brine solution. The organic layer was separated and dried over sodium sulfate, filtering and evaporation of the organic solvent under reduced pressure. The product was seperated by flash column chromatography using hexane and ethyl acetate (4:1) as an eluent to give colorless solid. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for XRD studies.

S3. Refinement

The hydrogen atoms were placed in calculated positions with C—H = 0.93 to 0.98 Å and O—H = 0.82 Å and refined in the riding model with isotropic displacement parameters: U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.
	Fig. 2. A view of the unit cell of the title compound viewed down a-axis; O—H···O intermolecular interactions are indicated by dashed lines.

2-[(4-Formylphenyl)(hydroxy)methyl]acrylonitrile

Crystal data

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) Å^3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.068P)^2 + 0.1498P] where P = (Fo^2 + 2Fc^2)/3
2778 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.99	2.8107 (15)	175

Symmetry code: (i) x+1, y−1, z.