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access(E)-3-(4-Chlorophenyl)-2-phenylprop-2-enoic acid
aDepartment of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan, bDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, cDepartment of Chemistry, GC University, Faisalabad, Pakistan, and dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: drsa54@yahoo.com
In the title molecule, C15H11ClO2, the mean planes of the benzene and phenyl rings are inclined at 69.06 (11)° with respect to each other. The is stablized by strong intermolecular O—H⋯O hydrogen bonds between the acid groups of pairs of molecules related by inversion centers.
Related literature
For background information, see: Canty & Van Koten (1995![[Canty, A. J. & Van Koten, G. (1995). Acc. Chem. Res. 28, 406-413.]](../../../../../../logos/arrows/e_arr.gif "Canty, A. J. & Van Koten, G. (1995). Acc. Chem. Res. 28, 406-413.")
). For a related structure, see: Sadiq-ur-Rehman et al. (2006). For a description of the Cambridge Structural Database, see: Allen (2002).
![[Scheme 1]](lh2835scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536809021904/lh2835sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536809021904/lh2835Isup2.hkl
A mixture of the phenylacetic acid (0.15 mol), p-chlorobenzaldehyde (0.15 mol), anhydrous K2CO3 (0.095 mol) and acetic anhydride (0.38 mol) was slowly raised to the temperature 353–373 K and maintained for 24 h. To a hot solution were added, 200 ml of H2O and 100 ml of 10% HCl. The mixture was stirred at room temperature for 2 h and filtered. The solid mass obtained was recrystallized from commercial ethanol. Colorless crystals suitable for crystallographic study were obtained after three weeks.
All the H-atoms were visible in the difference Fourier maps, they were included in the refinements at geometrically idealized positions with C—H and O—H distances = 0.95 and 0.84 Å, respectively, and Uiso = 1.5 and 1.2 times Ueq of the parent O and C-atoms respectively. The final difference map was free of chemically significant features.
Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./lh2835fig1thm.gif) | Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level. |
![[Figure 2]](./lh2835fig2thm.gif) | Fig. 2. Unit cell packing of (I) showing hydrogen bonding (dashed lines); H-atoms not involved in hydrogen bonding have been excluded for clarity. |
| C15H11ClO2 | F(000) = 536 |
| Mr = 258.69 | Dx = 1.374 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 10074 reflections |
| a = 14.405 (3) Å | θ = 1.8–27.5° |
| b = 5.733 (9) Å | µ = 0.30 mm−1 |
| c = 15.416 (9) Å | T = 173 K |
| β = 100.72 (3)° | Block, colourless |
| V = 1251 (2) Å3 | 0.16 × 0.10 × 0.04 mm |
| Z = 4 |
| Nonius KappaCCD diffractometer | 2860 independent reflections |
| Radiation source: fine-focus sealed tube | 1431 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.100 |
| ϕ and ω scans | θmax = 27.5°, θmin = 1.8° |
| Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −18→18 |
| Tmin = 0.954, Tmax = 0.988 | k = −7→7 |
| 10074 measured reflections | l = −19→19 |
| 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.130 | H-atom parameters constrained |
| S = 0.96 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
| 2860 reflections | (Δ/σ)max < 0.001 |
| 164 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.33 e Å−3 |
| C15H11ClO2 | V = 1251 (2) Å3 |
| Mr = 258.69 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 14.405 (3) Å | µ = 0.30 mm−1 |
| b = 5.733 (9) Å | T = 173 K |
| c = 15.416 (9) Å | 0.16 × 0.10 × 0.04 mm |
| β = 100.72 (3)° |
| Nonius KappaCCD diffractometer | 2860 independent reflections |
| Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 1431 reflections with I > 2σ(I) |
| Tmin = 0.954, Tmax = 0.988 | Rint = 0.100 |
| 10074 measured reflections |
| R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
| wR(F2) = 0.130 | H-atom parameters constrained |
| S = 0.96 | Δρmax = 0.22 e Å−3 |
| 2860 reflections | Δρmin = −0.33 e Å−3 |
| 164 parameters |
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 | ||
| Cl1 | 0.44668 (5) | 0.75005 (11) | −0.15436 (5) | 0.0494 (2) | |
| O1 | 0.01817 (12) | −0.2417 (3) | −0.06692 (11) | 0.0418 (5) | |
| H1 | −0.0181 | −0.3550 | −0.0639 | 0.063* | |
| O2 | 0.09332 (13) | −0.3917 (3) | 0.06070 (11) | 0.0464 (5) | |
| C1 | 0.24216 (16) | −0.0735 (4) | 0.07913 (14) | 0.0301 (6) | |
| C2 | 0.25291 (17) | 0.1160 (4) | 0.13702 (15) | 0.0331 (6) | |
| H2 | 0.2109 | 0.2448 | 0.1257 | 0.040* | |
| C3 | 0.32420 (18) | 0.1175 (4) | 0.21066 (16) | 0.0390 (6) | |
| H3 | 0.3305 | 0.2456 | 0.2504 | 0.047* | |
| C4 | 0.38652 (18) | −0.0687 (5) | 0.22627 (16) | 0.0406 (7) | |
| H4 | 0.4364 | −0.0668 | 0.2762 | 0.049* | |
| C5 | 0.37624 (18) | −0.2559 (5) | 0.16958 (17) | 0.0400 (6) | |
| H5 | 0.4191 | −0.3830 | 0.1806 | 0.048* | |
| C6 | 0.30376 (17) | −0.2607 (4) | 0.09650 (16) | 0.0337 (6) | |
| H6 | 0.2963 | −0.3922 | 0.0583 | 0.040* | |
| C7 | 0.16421 (16) | −0.0712 (4) | 0.00023 (15) | 0.0306 (6) | |
| C8 | 0.15911 (17) | 0.0761 (4) | −0.06802 (15) | 0.0339 (6) | |
| H8 | 0.1017 | 0.0727 | −0.1100 | 0.041* | |
| C9 | 0.08865 (17) | −0.2473 (4) | 0.00101 (16) | 0.0339 (6) | |
| C10 | 0.23076 (17) | 0.2420 (4) | −0.08639 (15) | 0.0323 (6) | |
| C11 | 0.32781 (18) | 0.2055 (4) | −0.05820 (17) | 0.0373 (6) | |
| H11 | 0.3488 | 0.0719 | −0.0236 | 0.045* | |
| C12 | 0.39343 (19) | 0.3591 (4) | −0.07955 (17) | 0.0390 (6) | |
| H12 | 0.4590 | 0.3313 | −0.0602 | 0.047* | |
| C13 | 0.36306 (18) | 0.5541 (4) | −0.12935 (16) | 0.0370 (6) | |
| C14 | 0.26819 (18) | 0.5965 (4) | −0.15954 (16) | 0.0388 (6) | |
| H14 | 0.2480 | 0.7306 | −0.1941 | 0.047* | |
| C15 | 0.20296 (18) | 0.4382 (4) | −0.13813 (15) | 0.0363 (6) | |
| H15 | 0.1376 | 0.4644 | −0.1594 | 0.044* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0473 (4) | 0.0393 (4) | 0.0664 (5) | −0.0059 (3) | 0.0232 (3) | 0.0088 (4) |
| O1 | 0.0376 (11) | 0.0454 (11) | 0.0395 (10) | −0.0145 (9) | −0.0006 (8) | 0.0038 (9) |
| O2 | 0.0481 (12) | 0.0473 (12) | 0.0414 (11) | −0.0173 (9) | 0.0016 (8) | 0.0092 (10) |
| C1 | 0.0326 (14) | 0.0279 (13) | 0.0315 (13) | −0.0053 (11) | 0.0109 (11) | 0.0003 (11) |
| C2 | 0.0369 (15) | 0.0277 (14) | 0.0361 (14) | −0.0018 (11) | 0.0101 (12) | 0.0001 (11) |
| C3 | 0.0445 (17) | 0.0379 (15) | 0.0346 (15) | −0.0090 (13) | 0.0076 (13) | −0.0065 (12) |
| C4 | 0.0342 (15) | 0.0536 (17) | 0.0336 (14) | −0.0064 (13) | 0.0052 (12) | 0.0052 (14) |
| C5 | 0.0358 (16) | 0.0398 (15) | 0.0465 (16) | 0.0048 (13) | 0.0130 (13) | 0.0108 (14) |
| C6 | 0.0370 (15) | 0.0295 (13) | 0.0365 (14) | −0.0043 (12) | 0.0118 (12) | −0.0020 (12) |
| C7 | 0.0293 (14) | 0.0312 (14) | 0.0315 (13) | −0.0035 (11) | 0.0063 (11) | −0.0043 (12) |
| C8 | 0.0320 (15) | 0.0350 (14) | 0.0345 (14) | −0.0015 (11) | 0.0053 (11) | −0.0045 (12) |
| C9 | 0.0332 (14) | 0.0351 (14) | 0.0329 (14) | −0.0051 (12) | 0.0052 (11) | −0.0046 (13) |
| C10 | 0.0383 (15) | 0.0309 (13) | 0.0287 (13) | −0.0054 (12) | 0.0091 (11) | −0.0039 (11) |
| C11 | 0.0404 (16) | 0.0316 (15) | 0.0423 (15) | 0.0012 (11) | 0.0141 (12) | 0.0038 (11) |
| C12 | 0.0360 (16) | 0.0362 (14) | 0.0472 (16) | −0.0005 (12) | 0.0143 (12) | 0.0036 (13) |
| C13 | 0.0440 (17) | 0.0283 (13) | 0.0425 (15) | −0.0059 (12) | 0.0178 (12) | −0.0019 (12) |
| C14 | 0.0455 (18) | 0.0338 (15) | 0.0401 (14) | 0.0008 (12) | 0.0157 (13) | 0.0052 (12) |
| C15 | 0.0369 (15) | 0.0389 (15) | 0.0339 (14) | 0.0030 (12) | 0.0090 (11) | −0.0002 (12) |
| Cl1—C13 | 1.742 (3) | C6—H6 | 0.9500 |
| O1—C9 | 1.316 (3) | C7—C8 | 1.340 (3) |
| O1—H1 | 0.8400 | C7—C9 | 1.486 (3) |
| O2—C9 | 1.230 (3) | C8—C10 | 1.469 (3) |
| C1—C6 | 1.386 (3) | C8—H8 | 0.9500 |
| C1—C2 | 1.396 (3) | C10—C15 | 1.393 (4) |
| C1—C7 | 1.494 (3) | C10—C11 | 1.400 (4) |
| C2—C3 | 1.382 (3) | C11—C12 | 1.376 (4) |
| C2—H2 | 0.9500 | C11—H11 | 0.9500 |
| C3—C4 | 1.387 (4) | C12—C13 | 1.380 (4) |
| C3—H3 | 0.9500 | C12—H12 | 0.9500 |
| C4—C5 | 1.375 (4) | C13—C14 | 1.381 (3) |
| C4—H4 | 0.9500 | C14—C15 | 1.390 (4) |
| C5—C6 | 1.387 (4) | C14—H14 | 0.9500 |
| C5—H5 | 0.9500 | C15—H15 | 0.9500 |
| C9—O1—H1 | 109.5 | C7—C8—H8 | 115.8 |
| C6—C1—C2 | 119.2 (2) | C10—C8—H8 | 115.8 |
| C6—C1—C7 | 121.4 (2) | O2—C9—O1 | 122.5 (2) |
| C2—C1—C7 | 119.4 (2) | O2—C9—C7 | 121.7 (2) |
| C3—C2—C1 | 120.5 (2) | O1—C9—C7 | 115.8 (2) |
| C3—C2—H2 | 119.8 | C15—C10—C11 | 117.5 (2) |
| C1—C2—H2 | 119.8 | C15—C10—C8 | 119.7 (2) |
| C2—C3—C4 | 119.7 (2) | C11—C10—C8 | 122.7 (2) |
| C2—C3—H3 | 120.1 | C12—C11—C10 | 121.4 (2) |
| C4—C3—H3 | 120.1 | C12—C11—H11 | 119.3 |
| C5—C4—C3 | 120.1 (2) | C10—C11—H11 | 119.3 |
| C5—C4—H4 | 120.0 | C11—C12—C13 | 119.4 (3) |
| C3—C4—H4 | 120.0 | C11—C12—H12 | 120.3 |
| C4—C5—C6 | 120.5 (2) | C13—C12—H12 | 120.3 |
| C4—C5—H5 | 119.7 | C14—C13—C12 | 121.4 (2) |
| C6—C5—H5 | 119.7 | C14—C13—Cl1 | 119.59 (19) |
| C1—C6—C5 | 120.0 (2) | C12—C13—Cl1 | 119.0 (2) |
| C1—C6—H6 | 120.0 | C13—C14—C15 | 118.4 (2) |
| C5—C6—H6 | 120.0 | C13—C14—H14 | 120.8 |
| C8—C7—C9 | 120.1 (2) | C15—C14—H14 | 120.8 |
| C8—C7—C1 | 124.6 (2) | C10—C15—C14 | 121.9 (2) |
| C9—C7—C1 | 115.3 (2) | C10—C15—H15 | 119.1 |
| C7—C8—C10 | 128.4 (2) | C14—C15—H15 | 119.1 |
| C6—C1—C2—C3 | 0.2 (3) | C1—C7—C9—O2 | −3.6 (3) |
| C7—C1—C2—C3 | 179.7 (2) | C8—C7—C9—O1 | −1.8 (3) |
| C1—C2—C3—C4 | 1.2 (4) | C1—C7—C9—O1 | 178.0 (2) |
| C2—C3—C4—C5 | −1.2 (4) | C7—C8—C10—C15 | −155.2 (3) |
| C3—C4—C5—C6 | 0.0 (4) | C7—C8—C10—C11 | 28.7 (4) |
| C2—C1—C6—C5 | −1.4 (3) | C15—C10—C11—C12 | 1.0 (3) |
| C7—C1—C6—C5 | 179.0 (2) | C8—C10—C11—C12 | 177.2 (2) |
| C4—C5—C6—C1 | 1.3 (4) | C10—C11—C12—C13 | 0.4 (4) |
| C6—C1—C7—C8 | −113.7 (3) | C11—C12—C13—C14 | −1.1 (4) |
| C2—C1—C7—C8 | 66.7 (3) | C11—C12—C13—Cl1 | 178.89 (19) |
| C6—C1—C7—C9 | 66.6 (3) | C12—C13—C14—C15 | 0.4 (4) |
| C2—C1—C7—C9 | −113.0 (3) | Cl1—C13—C14—C15 | −179.57 (18) |
| C9—C7—C8—C10 | −172.1 (2) | C11—C10—C15—C14 | −1.7 (3) |
| C1—C7—C8—C10 | 8.1 (4) | C8—C10—C15—C14 | −178.1 (2) |
| C8—C7—C9—O2 | 176.7 (2) | C13—C14—C15—C10 | 1.0 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.84 | 1.82 | 2.658 (3) | 177 |
| Symmetry code: (i) −x, −y−1, −z. |
Experimental details
| Crystal data | |
| Chemical formula | C15H11ClO2 |
| Mr | 258.69 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 173 |
| a, b, c (Å) | 14.405 (3), 5.733 (9), 15.416 (9) |
| β (°) | 100.72 (3) |
| V (Å3) | 1251 (2) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.30 |
| Crystal size (mm) | 0.16 × 0.10 × 0.04 |
| Data collection | |
| Diffractometer | Nonius KappaCCD diffractometer |
| Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
| Tmin, Tmax | 0.954, 0.988 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10074, 2860, 1431 |
| Rint | 0.100 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.130, 0.96 |
| No. of reflections | 2860 |
| No. of parameters | 164 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.22, −0.33 |
Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.84 | 1.82 | 2.658 (3) | 177 |
| Symmetry code: (i) −x, −y−1, −z. |
Acknowledgements
Quaid-i-Azam University, Islamabad is gratefully acknowledged for financial support.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Effort has been devoted to self assembly of organic and inorganic molecules in solid state because it extends a range of new solids with desirable physical and chemical properties (Canty & Van Koten, 1995). We report in this paper the crystal structure of the title compound (I) which has been synthesized in our laboratory.
The molecular structure of (I) is presented in Fig. 1. The benzene and phenyl rings are oriented at 69.06 (11)° with respect to each other. Molecules related by inversion ceneters form dimers via hydrogen bonds (Fig. 2); details of hydrogen bonding geometry have been given in Table 1. The molecular dimensions are normal (Allen, 2002). The cystal structure of a closely related compound has been previously reported from our laboratory (Sadiq-ur-Rehman et al., 2006).