3-(4-Chloro-phen-yl)-2-methyl-acrylic acid.

In the crystal structure of the title compound, C(10)H(9)ClO(2), dimers form as a result of inter-molecular O-H⋯O bonding. These dimers are linked to each other via C-H⋯O bonds, where the CH group belongs to the benzene ring and the O atom is from the carbonyl group of an adjacent mol-ecule. There exist two inter-molecular C-H⋯O hydrogen bonds, which individually form five-membered rings. There also exists a π-π inter-action between the aromatic ring and its symmetry counterpart, with a centroid-centroid distance of 4.0202 (17) Å, and a C-H⋯π inter-action between a methyl CH group and the aromatic ring.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Bravo (1998 ▶); Burt (2004 ▶); Hertog et al. (1995 ▶); Muhammad et al. (2007a ▶,b ▶, 2008a ▶,b ▶); Muhammad, Ali et al. (2008 ▶); Niaz et al. (2008 ▶).

Experimental

Crystal data

C10H9ClO2

M = 196.62

Triclinic,

a = 7.2164 (6) Å

b = 8.2746 (7) Å

c = 9.1762 (8) Å

α = 115.182 (4)°

β = 108.022 (4)°

γ = 90.052 (5)°

V = 465.91 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 296 (2) K

0.28 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.910, T max = 0.930

7513 measured reflections

2692 independent reflections

1782 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.217

S = 1.10

2692 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022198/bq2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022198/bq2090Isup2.hkl

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

C10H9ClO2	Z = 2
Mr = 196.62	F000 = 204
Triclinic, P1	Dx = 1.402 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.2164 (6) Å	Cell parameters from 2692 reflections
b = 8.2746 (7) Å	θ = 2.6–30.3º
c = 9.1762 (8) Å	µ = 0.37 mm−1
α = 115.182 (4)º	T = 296 (2) K
β = 108.022 (4)º	Prism, colourless
γ = 90.052 (5)º	0.28 × 0.20 × 0.18 mm
V = 465.91 (7) Å3

Bruker Kappa APEXII CCD diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 7.2 pixels mm-1	θmax = 30.3º
T = 296(2) K	θmin = 2.6º
ω scans	h = −10→8
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −10→11
Tmin = 0.910, Tmax = 0.930	l = −12→12
7513 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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.217	w = 1/[σ2(Fo2) + (0.1083P)2 + 0.1931P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2692 reflections	Δρmax = 0.53 e Å−3
122 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction coefficient: ?

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 e.s.d.'s 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
Cl1	0.80795 (12)	0.09608 (15)	0.42599 (12)	0.0771 (4)
O1	−0.2602 (3)	0.5461 (3)	0.1669 (2)	0.0510 (6)
O2	−0.3959 (3)	0.3388 (3)	−0.1034 (2)	0.0543 (6)
C1	−0.2554 (3)	0.4027 (3)	0.0322 (3)	0.0390 (7)
C2	−0.0735 (3)	0.3196 (3)	0.0525 (3)	0.0371 (7)
C3	−0.0680 (4)	0.1670 (4)	−0.1102 (3)	0.0484 (8)
C4	0.0606 (3)	0.3764 (3)	0.2098 (3)	0.0403 (7)
C5	0.2464 (3)	0.3096 (3)	0.2602 (3)	0.0364 (6)
C6	0.3638 (4)	0.2508 (4)	0.1573 (3)	0.0432 (8)
C7	0.5363 (4)	0.1864 (4)	0.2086 (3)	0.0461 (8)
C8	0.5923 (4)	0.1793 (4)	0.3641 (3)	0.0438 (7)
C9	0.4803 (4)	0.2379 (4)	0.4686 (3)	0.0493 (8)
C10	0.3099 (4)	0.3051 (4)	0.4171 (3)	0.0451 (7)
H1	−0.377 (5)	0.580 (5)	0.142 (5)	0.0612*
H3A	−0.19861	0.10124	−0.17914	0.0725*
H3B	0.01747	0.08750	−0.08293	0.0725*
H3C	−0.01950	0.21487	−0.17241	0.0725*
H4	0.03229	0.46997	0.29797	0.0484*
H6	0.32524	0.25512	0.05263	0.0518*
H7	0.61382	0.14812	0.13947	0.0554*
H9	0.51873	0.23233	0.57269	0.0592*
H10	0.23624	0.34816	0.48924	0.0541*

	U11	U22	U33	U12	U13	U23
Cl1	0.0555 (5)	0.1129 (8)	0.0698 (6)	0.0449 (5)	0.0181 (4)	0.0492 (5)
O1	0.0415 (10)	0.0576 (12)	0.0430 (10)	0.0207 (8)	0.0116 (8)	0.0147 (9)
O2	0.0436 (10)	0.0686 (13)	0.0391 (10)	0.0217 (9)	0.0075 (8)	0.0183 (9)
C1	0.0377 (11)	0.0459 (13)	0.0373 (12)	0.0117 (10)	0.0140 (9)	0.0213 (10)
C2	0.0357 (11)	0.0379 (12)	0.0411 (12)	0.0091 (9)	0.0141 (9)	0.0202 (10)
C3	0.0444 (13)	0.0477 (14)	0.0430 (13)	0.0116 (11)	0.0115 (11)	0.0138 (11)
C4	0.0365 (11)	0.0418 (12)	0.0395 (12)	0.0109 (9)	0.0122 (9)	0.0160 (10)
C5	0.0335 (10)	0.0351 (11)	0.0363 (11)	0.0060 (9)	0.0105 (9)	0.0131 (9)
C6	0.0397 (12)	0.0562 (15)	0.0408 (12)	0.0112 (10)	0.0143 (10)	0.0276 (12)
C7	0.0359 (11)	0.0604 (16)	0.0443 (13)	0.0130 (11)	0.0152 (10)	0.0245 (12)
C8	0.0349 (11)	0.0487 (14)	0.0413 (12)	0.0103 (10)	0.0060 (10)	0.0192 (11)
C9	0.0461 (13)	0.0627 (17)	0.0323 (12)	0.0133 (12)	0.0063 (10)	0.0200 (12)
C10	0.0412 (12)	0.0563 (15)	0.0310 (11)	0.0105 (11)	0.0116 (10)	0.0141 (11)

Cl1—C8	1.734 (3)	C7—C8	1.385 (4)
O1—C1	1.310 (3)	C8—C9	1.376 (4)
O2—C1	1.231 (3)	C9—C10	1.382 (4)
O1—H1	0.88 (4)	C3—H3A	0.9600
C1—C2	1.480 (3)	C3—H3B	0.9600
C2—C3	1.503 (4)	C3—H3C	0.9600
C2—C4	1.341 (3)	C4—H4	0.9300
C4—C5	1.467 (3)	C6—H6	0.9300
C5—C10	1.386 (4)	C7—H7	0.9300
C5—C6	1.397 (4)	C9—H9	0.9300
C6—C7	1.381 (4)	C10—H10	0.9300
C1—O1—H1	109 (3)	C5—C10—C9	121.4 (2)
O1—C1—O2	121.8 (2)	C2—C3—H3A	109.00
O1—C1—C2	116.5 (2)	C2—C3—H3B	109.00
O2—C1—C2	121.7 (2)	C2—C3—H3C	109.00
C1—C2—C4	118.9 (2)	H3A—C3—H3B	109.00
C3—C2—C4	126.8 (2)	H3A—C3—H3C	109.00
C1—C2—C3	114.2 (2)	H3B—C3—H3C	110.00
C2—C4—C5	128.1 (2)	C2—C4—H4	116.00
C4—C5—C10	118.9 (2)	C5—C4—H4	116.00
C6—C5—C10	118.1 (2)	C5—C6—H6	119.00
C4—C5—C6	122.9 (2)	C7—C6—H6	119.00
C5—C6—C7	121.0 (2)	C6—C7—H7	120.00
C6—C7—C8	119.2 (3)	C8—C7—H7	120.00
Cl1—C8—C7	118.7 (2)	C8—C9—H9	120.00
Cl1—C8—C9	120.3 (2)	C10—C9—H9	120.00
C7—C8—C9	120.9 (3)	C5—C10—H10	119.00
C8—C9—C10	119.2 (3)	C9—C10—H10	119.00
O1—C1—C2—C3	−174.4 (2)	C10—C5—C6—C7	1.3 (5)
O1—C1—C2—C4	9.9 (4)	C4—C5—C10—C9	177.8 (3)
O2—C1—C2—C3	6.7 (4)	C6—C5—C10—C9	−2.5 (5)
O2—C1—C2—C4	−169.1 (3)	C5—C6—C7—C8	0.4 (5)
C1—C2—C4—C5	177.8 (3)	C6—C7—C8—Cl1	179.4 (3)
C3—C2—C4—C5	2.6 (5)	C6—C7—C8—C9	−1.0 (5)
C2—C4—C5—C6	35.4 (4)	Cl1—C8—C9—C10	179.5 (3)
C2—C4—C5—C10	−145.0 (3)	C7—C8—C9—C10	−0.2 (5)
C4—C5—C6—C7	−179.0 (3)	C8—C9—C10—C5	2.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.88 (4)	1.76 (4)	2.643 (3)	176.4 (14)
C3—H3A···O2	0.96	2.41	2.765 (4)	101
C4—H4···O1	0.93	2.32	2.720 (3)	106
C9—H9···O2ii	0.93	2.57	3.458 (3)	159
C3—H3a···Cgiii	0.96	2.84	3.638 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.88 (4)	1.76 (4)	2.643 (3)	176.4 (14)
C3—H3A⋯O2	0.96	2.41	2.765 (4)	101
C4—H4⋯O1	0.93	2.32	2.720 (3)	106
C9—H9⋯O2ii	0.93	2.57	3.458 (3)	159
C3—H3a⋯Cgiii	0.96	2.84	3.638 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C5–C10 ring.