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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1542
doi:10.1107/S1600536808022198

3-(4-Chloro­phen­yl)-2-methyl­acrylic acid

Niaz Muhammad,a Muhammad Nawaz Tahir,b* Zia-ur-Rehman,a Saqib Alia and Farkhanda Shaheena

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 July 2008; accepted 15 July 2008; online 19 July 2008)

In the crystal structure of the title compound, C10H9ClO2, dimers form as a result of inter­molecular 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 mol­ecule. There exist two inter­molecular C—H⋯O hydrogen bonds, which individually form five-membered rings. There also exists a π–π inter­action between the aromatic ring and its symmetry counterpart, with a centroid–centroid distance of 4.0202 (17) Å, and a C—H⋯π inter­action between a methyl CH group and the aromatic ring.

Related literature

For related literature, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Bravo (1998[Bravo, L. (1998). Nutr. Rev. 56, 317-333.]); Burt (2004[Burt, S. (2004). Int. J. Food Microbiol. 94, 223-253.]); Hertog et al. (1995[Hertog, M. G., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Fidanza, F., Giampaoli, S., Jansen, A., Menotti, A. & Nedeljkovic, S. (1995). Arch. Intern. Med. 155, 381-386.]); Muhammad et al. (2007a[Muhammad, N., Zia-ur-Rehman,, Ali, S. & Meetsma, A. (2007a). Acta Cryst. E63, o2174-o2175.],b[Muhammad, N., Zia-ur-Rehman,, Ali, S. & Meetsma, A. (2007b). Acta Cryst. E63, o2557-o2558.], 2008a[Muhammad, N., Tahir, M. N., Ali, S. & Zia-ur-Rehman, (2008a). Acta Cryst. E64, m946-m947.],b[Muhammad, N., Tahir, M. N., Ali, S. & Zia-ur-Rehman, (2008b). Acta Cryst. E64, m978.]); Muhammad, Ali et al. (2008[Muhammad, N., Ali, S., Tahir, M. N. & Zia-ur-Rehman, (2008). Acta Cryst. E64, o1373.]); Niaz et al. (2008[Niaz, M., Tahir, M. N., Zia-ur-Rehman,, Ali, S. & Khan, I. U. (2008). Acta Cryst. E64, o733.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9ClO2

  • Mr = 196.62

  • Triclinic, [P \overline 1]

  • 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[Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.910, Tmax = 0.930

  • 7513 measured reflections

  • 2692 independent reflections

  • 1782 reflections with I > 2σ(I)

  • Rint = 0.029
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 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

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) -x-1, -y+1, -z; (ii) x+1, y, z+1; (iii) -x, -y, -z. Cg is the centroid of the C5–C10 ring.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

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

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

checkCIF report


Comment top

Cinnamic acids compose a relatively large family of organic acid isomers (Bravo, 1998). In nature, cinnamic acid derivatives are important metabolic building blocks in the production of lignins for higher plants. Cinnamic acid possesses antibacterial, antifungal and parasite fighting abilities (Burt, 2004). A derivative of cinnamic acid is an important pharmaceutical for high blood pressure, stroke prevention and possess antitumour activity (Hertog et al., 1995). In continuation of our efforts to synthesize various derivatives of cinnamic acids (Niaz et al., 2008, Muhammad, Ali et al., 2008) and their tin complexes (Muhammad et al., 2008a, 2008b), we herein report the structure of the title compound (I).

The crystal structure of 3-(4-Bromophenyl)-2-methylacrylic acid (II) (Muhammad et al., 2007a) and 3-(4-Bromophenyl)-2-ethylacrylic acid (Muhammad et al., 2007b) has been previously reported. The title compound (I) have a replacement of Br-atom with Cl-atom. Thus the reported compound (II) is the best example for the comparison of bond geometry etc.

In the crystal structure of the title compound, the C—C bonds are in the range [1.467 (3)–1.503 (4) Å], and C==C have a value of 1.341 (3) Å. The resonant C—O bonds have values of 1.231 (3) and 1.310 (3) Å. In the asymmetric unit, there are two intermolecular H-bonds of C—H···O type (Table 2, Fig 1). Due to these H-bonds two five membered rings (O1/C1/C2/C4/H4···O1) and (O2/C1/C2/C3/H3A···O2) are formed. Centrosymmetric dimers, R22(8) (Bernstein et al. 1995) are formed due to the intermolecular O1—H1···O2i [symmetry code: i = -x - 1, -y + 1, -z] hydrogen bonding. These dimers are linked to each other by intermolecular H-bonding, C9—H9···O2ii [symmetry code: ii = x + 1, y, z + 1] as shown in Fig 2. There exist an interaction, C3—H3A···Cgiii [symmetry code: iii = -x, -y, -z] with a distance of 3.638 (3) Å between C3 and Cgiii [Cg is the center of the (C5-C10) benzene ring]. There also exist a π···π-interaction between the benzene rings of adjacent molecules. The distance between the centroids of Cg and Cgiv [symmetry code: iv = -x + 1, -y + 1, -z + 1], is 4.0202 (17) Å.

Related literature top

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 top

Compound (I) was prepared according to the reported procedure (Muhammad et al., 2007a). A mixture of 4-chlorobenzaldehyde (1.40 g, 10 mmol), methylmalonic acid (2.36 g, 20 mmol) and piperidine (1.98 ml, 20 mmol) in a pyridine (12.5 ml) solution was heated on a steam-bath for 24 h. The reaction mixture was cooled and added to a mixture of 25 ml of concentrated HCl and 50 g of ice. The precipitate formed in the acidified mixture was filtered off and washed with ice-cold water. The product was recrystallized from ethanol. The yield was 89%.

Refinement top

The coordinates of H atom attached to O1 were refined freely. All other H atoms were positioned geometrically, C—H = 0.93, and 0.96 Å for aromatic and methyl H, and constrained to ride on their parent atoms and were treated as isotropic with Uiso(H) = xUeq(C,O), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); 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 (Spek, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of (I) with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. The intramolecular H-bonds are shown by doted lines.
[Figure 2] Fig. 2. The packing figure (PLATON: Spek, 2003) which shows the dimeric nature of the compound and the interlinkages of the dimers.
3-(4-Chlorophenyl)-2-methylacrylic acid top
Crystal data top
C10H9ClO2Z = 2
Mr = 196.62F(000) = 204
Triclinic, P1Dx = 1.402 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2164 (6) ÅCell parameters from 2692 reflections
b = 8.2746 (7) Åθ = 2.6–30.3°
c = 9.1762 (8) ŵ = 0.37 mm−1
α = 115.182 (4)°T = 296 K
β = 108.022 (4)°Prism, colourless
γ = 90.052 (5)°0.28 × 0.20 × 0.18 mm
V = 465.91 (7) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2692 independent reflections
Radiation source: fine-focus sealed tube1782 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 7.2 pixels mm-1θmax = 30.3°, θmin = 2.6°
ω scansh = −10→8
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −10→11
Tmin = 0.910, Tmax = 0.930l = −12→12
7513 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.1083P)2 + 0.1931P]
where P = (Fo2 + 2Fc2)/3
2692 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C10H9ClO2γ = 90.052 (5)°
Mr = 196.62V = 465.91 (7) Å3
Triclinic, P1Z = 2
a = 7.2164 (6) ÅMo Kα radiation
b = 8.2746 (7) ŵ = 0.37 mm−1
c = 9.1762 (8) ÅT = 296 K
α = 115.182 (4)°0.28 × 0.20 × 0.18 mm
β = 108.022 (4)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2692 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1782 reflections with I > 2σ(I)
Tmin = 0.910, Tmax = 0.930Rint = 0.029
7513 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.217H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.53 e Å−3
2692 reflectionsΔρmin = −0.27 e Å−3
122 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.80795 (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)
C40.0606 (3)0.3764 (3)0.2098 (3)0.0403 (7)
C50.2464 (3)0.3096 (3)0.2602 (3)0.0364 (6)
C60.3638 (4)0.2508 (4)0.1573 (3)0.0432 (8)
C70.5363 (4)0.1864 (4)0.2086 (3)0.0461 (8)
C80.5923 (4)0.1793 (4)0.3641 (3)0.0438 (7)
C90.4803 (4)0.2379 (4)0.4686 (3)0.0493 (8)
C100.3099 (4)0.3051 (4)0.4171 (3)0.0451 (7)
H1−0.377 (5)0.580 (5)0.142 (5)0.0612*
H3A−0.198610.10124−0.179140.0725*
H3B0.017470.08750−0.082930.0725*
H3C−0.019500.21487−0.172410.0725*
H40.032290.469970.297970.0484*
H60.325240.255120.052630.0518*
H70.613820.148120.139470.0554*
H90.518730.232330.572690.0592*
H100.236240.348160.489240.0541*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0555 (5)0.1129 (8)0.0698 (6)0.0449 (5)0.0181 (4)0.0492 (5)
O10.0415 (10)0.0576 (12)0.0430 (10)0.0207 (8)0.0116 (8)0.0147 (9)
O20.0436 (10)0.0686 (13)0.0391 (10)0.0217 (9)0.0075 (8)0.0183 (9)
C10.0377 (11)0.0459 (13)0.0373 (12)0.0117 (10)0.0140 (9)0.0213 (10)
C20.0357 (11)0.0379 (12)0.0411 (12)0.0091 (9)0.0141 (9)0.0202 (10)
C30.0444 (13)0.0477 (14)0.0430 (13)0.0116 (11)0.0115 (11)0.0138 (11)
C40.0365 (11)0.0418 (12)0.0395 (12)0.0109 (9)0.0122 (9)0.0160 (10)
C50.0335 (10)0.0351 (11)0.0363 (11)0.0060 (9)0.0105 (9)0.0131 (9)
C60.0397 (12)0.0562 (15)0.0408 (12)0.0112 (10)0.0143 (10)0.0276 (12)
C70.0359 (11)0.0604 (16)0.0443 (13)0.0130 (11)0.0152 (10)0.0245 (12)
C80.0349 (11)0.0487 (14)0.0413 (12)0.0103 (10)0.0060 (10)0.0192 (11)
C90.0461 (13)0.0627 (17)0.0323 (12)0.0133 (12)0.0063 (10)0.0200 (12)
C100.0412 (12)0.0563 (15)0.0310 (11)0.0105 (11)0.0116 (10)0.0141 (11)
Geometric parameters (Å, º) top
Cl1—C81.734 (3)C7—C81.385 (4)
O1—C11.310 (3)C8—C91.376 (4)
O2—C11.231 (3)C9—C101.382 (4)
O1—H10.88 (4)C3—H3A0.9600
C1—C21.480 (3)C3—H3B0.9600
C2—C31.503 (4)C3—H3C0.9600
C2—C41.341 (3)C4—H40.9300
C4—C51.467 (3)C6—H60.9300
C5—C101.386 (4)C7—H70.9300
C5—C61.397 (4)C9—H90.9300
C6—C71.381 (4)C10—H100.9300
C1—O1—H1109 (3)C5—C10—C9121.4 (2)
O1—C1—O2121.8 (2)C2—C3—H3A109.00
O1—C1—C2116.5 (2)C2—C3—H3B109.00
O2—C1—C2121.7 (2)C2—C3—H3C109.00
C1—C2—C4118.9 (2)H3A—C3—H3B109.00
C3—C2—C4126.8 (2)H3A—C3—H3C109.00
C1—C2—C3114.2 (2)H3B—C3—H3C110.00
C2—C4—C5128.1 (2)C2—C4—H4116.00
C4—C5—C10118.9 (2)C5—C4—H4116.00
C6—C5—C10118.1 (2)C5—C6—H6119.00
C4—C5—C6122.9 (2)C7—C6—H6119.00
C5—C6—C7121.0 (2)C6—C7—H7120.00
C6—C7—C8119.2 (3)C8—C7—H7120.00
Cl1—C8—C7118.7 (2)C8—C9—H9120.00
Cl1—C8—C9120.3 (2)C10—C9—H9120.00
C7—C8—C9120.9 (3)C5—C10—H10119.00
C8—C9—C10119.2 (3)C9—C10—H10119.00
O1—C1—C2—C3−174.4 (2)C10—C5—C6—C71.3 (5)
O1—C1—C2—C49.9 (4)C4—C5—C10—C9177.8 (3)
O2—C1—C2—C36.7 (4)C6—C5—C10—C9−2.5 (5)
O2—C1—C2—C4−169.1 (3)C5—C6—C7—C80.4 (5)
C1—C2—C4—C5177.8 (3)C6—C7—C8—Cl1179.4 (3)
C3—C2—C4—C52.6 (5)C6—C7—C8—C9−1.0 (5)
C2—C4—C5—C635.4 (4)Cl1—C8—C9—C10179.5 (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—C52.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.88 (4)1.76 (4)2.643 (3)176.4 (14)
C3—H3A···O20.962.412.765 (4)101
C4—H4···O10.932.322.720 (3)106
C9—H9···O2ii0.932.573.458 (3)159
C3—H3a···Cgiii0.962.843.638 (3)141
Symmetry codes: (i) −x−1, −y+1, −z; (ii) x+1, y, z+1; (iii) −x, −y, −z.

Experimental details

Crystal data
Chemical formulaC10H9ClO2
Mr196.62
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.2164 (6), 8.2746 (7), 9.1762 (8)
α, β, γ (°)115.182 (4), 108.022 (4), 90.052 (5)
V (Å3)465.91 (7)
Z2
Radiation typeMo Kα
µ (mm−1)0.37
Crystal size (mm)0.28 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.910, 0.930
No. of measured, independent and
observed [I > 2σ(I)] reflections		7513, 2692, 1782
Rint0.029
(sin θ/λ)max (Å−1)0.709
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.217, 1.10
No. of reflections2692
No. of parameters122
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.53, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.88 (4)1.76 (4)2.643 (3)176.4 (14)
C3—H3A···O20.962.412.765 (4)101
C4—H4···O10.932.322.720 (3)106
C9—H9···O2ii0.932.573.458 (3)159
C3—H3a···Cgiii0.962.843.638 (3)141
Symmetry codes: (i) −x−1, −y+1, −z; (ii) x+1, y, z+1; (iii) −x, −y, −z.
 

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for financial support to NM for a PhD under the Indigenous Scholarship Scheme.

References

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ISSN: 2056-9890
Volume 64| Part 8| August 2008| Page o1542
doi:10.1107/S1600536808022198
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