2-[(2-Chloro-quinolin-3-yl)(hy-droxy)meth-yl]acrylo-nitrile.

In the title compound, C13H9ClN2O, the dihedral angle between the acrylo-nitrile C=C-CN plane and the quilonine ring system is 71.3 (2)°. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming chains along [01-1]. The chains are linked into a three-dimensional network through C-H⋯N inter-actions.

Related literature

For the biological activity of quinoline and arcylo­nitrile compounds, see: Dutta et al. (2002 ▶); Ohsumi et al. (1998 ▶); Saczewski et al. (2004 ▶).

Experimental

Crystal data

C13H9ClN2O

M = 244.67

Orthorhombic,

a = 12.2879 (12) Å

b = 9.6422 (11) Å

c = 10.3642 (12) Å

V = 1228.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.943, T max = 0.971

6334 measured reflections

2423 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.02

2423 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 819 Friedel pairs

Flack parameter: 0.02 (7)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010155/is5260sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010155/is5260Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010155/is5260Isup3.cml

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

C13H9ClN2O	F(000) = 504
Mr = 244.67	Dx = 1.323 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2423 reflections
a = 12.2879 (12) Å	θ = 2.7–28.3°
b = 9.6422 (11) Å	µ = 0.30 mm−1
c = 10.3642 (12) Å	T = 293 K
V = 1228.0 (2) Å3	Block, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Bruker SMART APEXII area-detector diffractometer	2423 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −15→16
Tmin = 0.943, Tmax = 0.971	k = −12→11
6334 measured reflections	l = −13→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.0827P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.14 e Å−3
2423 reflections	Δρmin = −0.14 e Å−3
156 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 819 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (7)

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
Cl	0.29993 (4)	1.02688 (6)	0.48433 (7)	0.06601 (17)
O1	0.22815 (13)	0.60309 (15)	0.62021 (17)	0.0682 (4)
H1	0.2656	0.5770	0.6811	0.102*
N1	0.16299 (12)	0.95206 (16)	0.30888 (16)	0.0476 (3)
N2	−0.02036 (17)	0.7266 (3)	0.7546 (3)	0.0870 (7)
C1	0.20463 (12)	0.91298 (18)	0.41795 (18)	0.0438 (4)
C2	0.08750 (12)	0.86715 (18)	0.25212 (17)	0.0441 (4)
C3	0.04132 (16)	0.9065 (2)	0.1326 (2)	0.0574 (5)
H3	0.0617	0.9897	0.0941	0.069*
C4	−0.03276 (18)	0.8230 (2)	0.0741 (2)	0.0643 (5)
H4	−0.0628	0.8496	−0.0045	0.077*
C5	−0.06450 (18)	0.6974 (3)	0.1306 (2)	0.0698 (6)
H5	−0.1157	0.6418	0.0894	0.084*
C6	−0.02145 (18)	0.6556 (2)	0.2451 (2)	0.0637 (5)
H6	−0.0428	0.5716	0.2813	0.076*
C7	0.05581 (13)	0.73997 (18)	0.30916 (19)	0.0467 (4)
C8	0.10462 (14)	0.70438 (18)	0.42751 (19)	0.0500 (4)
H8	0.0850	0.6219	0.4678	0.060*
C9	0.18017 (11)	0.78848 (16)	0.4845 (2)	0.0427 (3)
C10	0.23288 (14)	0.7498 (2)	0.6112 (2)	0.0499 (4)
H10	0.3091	0.7796	0.6106	0.060*
C11	0.17479 (15)	0.8165 (2)	0.7227 (2)	0.0531 (4)
C12	0.06476 (15)	0.7679 (2)	0.7430 (2)	0.0596 (5)
C13	0.2182 (2)	0.9086 (3)	0.8014 (3)	0.0818 (8)
H13A	0.1780	0.9428	0.8704	0.098*
H13B	0.2890	0.9394	0.7878	0.098*

	U11	U22	U33	U12	U13	U23
Cl	0.0630 (2)	0.0706 (3)	0.0645 (3)	−0.0222 (2)	−0.0026 (3)	0.0007 (3)
O1	0.0915 (10)	0.0563 (8)	0.0569 (9)	0.0187 (7)	−0.0204 (8)	0.0116 (7)
N1	0.0539 (7)	0.0462 (8)	0.0426 (8)	−0.0018 (6)	0.0047 (7)	0.0098 (6)
N2	0.0582 (10)	0.1206 (18)	0.0821 (17)	−0.0155 (11)	0.0037 (10)	−0.0078 (14)
C1	0.0430 (7)	0.0452 (8)	0.0432 (9)	−0.0038 (6)	0.0047 (7)	0.0019 (7)
C2	0.0484 (7)	0.0457 (8)	0.0382 (9)	0.0043 (6)	0.0028 (7)	0.0058 (7)
C3	0.0692 (10)	0.0596 (11)	0.0433 (11)	0.0076 (9)	0.0002 (9)	0.0132 (9)
C4	0.0708 (11)	0.0765 (14)	0.0456 (11)	0.0133 (10)	−0.0115 (10)	0.0020 (10)
C5	0.0709 (11)	0.0768 (14)	0.0616 (14)	−0.0064 (10)	−0.0156 (12)	−0.0068 (12)
C6	0.0722 (11)	0.0581 (11)	0.0609 (14)	−0.0126 (9)	−0.0076 (11)	0.0040 (10)
C7	0.0521 (8)	0.0450 (9)	0.0430 (10)	0.0008 (7)	−0.0004 (8)	0.0041 (7)
C8	0.0586 (8)	0.0426 (8)	0.0487 (10)	−0.0024 (7)	−0.0025 (8)	0.0123 (7)
C9	0.0456 (6)	0.0449 (8)	0.0376 (8)	0.0054 (5)	−0.0010 (8)	0.0059 (8)
C10	0.0493 (8)	0.0561 (10)	0.0443 (9)	0.0061 (7)	−0.0079 (8)	0.0077 (8)
C11	0.0526 (8)	0.0632 (11)	0.0436 (10)	−0.0009 (8)	−0.0064 (8)	0.0053 (9)
C12	0.0574 (10)	0.0746 (13)	0.0469 (11)	0.0031 (9)	−0.0044 (9)	−0.0002 (9)
C13	0.0761 (13)	0.102 (2)	0.0678 (16)	−0.0144 (13)	0.0020 (13)	−0.0238 (16)

Cl—C1	1.7466 (17)	C5—H5	0.9300
O1—C10	1.419 (3)	C6—C7	1.416 (3)
O1—H1	0.8200	C6—H6	0.9300
N1—C1	1.297 (2)	C7—C8	1.408 (3)
N1—C2	1.370 (2)	C8—C9	1.367 (2)
N2—C12	1.125 (3)	C8—H8	0.9300
C1—C9	1.417 (2)	C9—C10	1.511 (3)
C2—C3	1.414 (3)	C10—C11	1.504 (3)
C2—C7	1.416 (2)	C10—H10	0.9800
C3—C4	1.358 (3)	C11—C13	1.318 (3)
C3—H3	0.9300	C11—C12	1.447 (3)
C4—C5	1.401 (4)	C13—H13A	0.9300
C4—H4	0.9300	C13—H13B	0.9300
C5—C6	1.360 (3)
C10—O1—H1	109.5	C8—C7—C2	117.24 (16)
C1—N1—C2	117.89 (15)	C6—C7—C2	119.12 (18)
N1—C1—C9	125.93 (16)	C9—C8—C7	121.42 (16)
N1—C1—Cl	115.16 (13)	C9—C8—H8	119.3
C9—C1—Cl	118.90 (14)	C7—C8—H8	119.3
N1—C2—C3	119.17 (16)	C8—C9—C1	115.88 (17)
N1—C2—C7	121.64 (16)	C8—C9—C10	121.34 (16)
C3—C2—C7	119.19 (17)	C1—C9—C10	122.78 (15)
C4—C3—C2	120.07 (18)	O1—C10—C11	110.90 (18)
C4—C3—H3	120.0	O1—C10—C9	106.62 (16)
C2—C3—H3	120.0	C11—C10—C9	111.04 (14)
C3—C4—C5	120.80 (19)	O1—C10—H10	109.4
C3—C4—H4	119.6	C11—C10—H10	109.4
C5—C4—H4	119.6	C9—C10—H10	109.4
C6—C5—C4	120.8 (2)	C13—C11—C12	120.5 (2)
C6—C5—H5	119.6	C13—C11—C10	124.89 (19)
C4—C5—H5	119.6	C12—C11—C10	114.60 (17)
C5—C6—C7	120.0 (2)	N2—C12—C11	177.2 (3)
C5—C6—H6	120.0	C11—C13—H13A	120.0
C7—C6—H6	120.0	C11—C13—H13B	120.0
C8—C7—C6	123.64 (17)	H13A—C13—H13B	120.0
C2—N1—C1—C9	0.7 (3)	C2—C7—C8—C9	−0.6 (3)
C2—N1—C1—Cl	−179.85 (13)	C7—C8—C9—C1	0.7 (3)
C1—N1—C2—C3	−179.50 (16)	C7—C8—C9—C10	−179.68 (17)
C1—N1—C2—C7	−0.5 (2)	N1—C1—C9—C8	−0.8 (3)
N1—C2—C3—C4	179.27 (18)	Cl—C1—C9—C8	179.74 (13)
C7—C2—C3—C4	0.2 (3)	N1—C1—C9—C10	179.58 (17)
C2—C3—C4—C5	0.0 (3)	Cl—C1—C9—C10	0.2 (2)
C3—C4—C5—C6	−0.4 (4)	C8—C9—C10—O1	25.3 (2)
C4—C5—C6—C7	0.5 (4)	C1—C9—C10—O1	−155.10 (16)
C5—C6—C7—C8	−179.8 (2)	C8—C9—C10—C11	−95.6 (2)
C5—C6—C7—C2	−0.3 (3)	C1—C9—C10—C11	84.0 (2)
N1—C2—C7—C8	0.4 (2)	O1—C10—C11—C13	125.4 (2)
C3—C2—C7—C8	179.43 (17)	C9—C10—C11—C13	−116.3 (3)
N1—C2—C7—C6	−179.12 (18)	O1—C10—C11—C12	−52.3 (2)
C3—C2—C7—C6	−0.1 (3)	C9—C10—C11—C12	66.1 (2)
C6—C7—C8—C9	178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.99	2.781 (2)	161
C10—H10···N2ii	0.98	2.57	3.385 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.99	2.781 (2)	161
C10—H10⋯N2ii	0.98	2.57	3.385 (3)	140

Symmetry codes: (i) ; (ii) .