(E)-3-(4-Chloro­phen­yl)-2-phenyl­prop-2-enoic acid

Abstract

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 crystal structure 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 ▶). For a related structure, see: Sadiq-ur-Rehman et al. (2006 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

• C₁₅H₁₁ClO₂

• M _r = 258.69

• Monoclinic,

• a = 14.405 (3) Å

• b = 5.733 (9) Å

• c = 15.416 (9) Å

• β = 100.72 (3)°

• V = 1251 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.30 mm⁻¹

• T = 173 K

• 0.16 × 0.10 × 0.04 mm

Data collection

• Nonius KappaCCD diffractometer

• Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.954, T _max = 0.988

• 10074 measured reflections

• 2860 independent reflections

• 1431 reflections with I > 2σ(I)

• R _int = 0.100

Refinement

• R[F ² > 2σ(F ²)] = 0.047

• wR(F ²) = 0.130

• S = 0.96

• 2860 reflections

• 164 parameters

• H-atom parameters constrained

• Δρ_max = 0.22 e Å⁻³

• Δρ_min = −0.33 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: 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 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

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) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

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 U_iso = 1.5 and 1.2 times U_eq of the parent O and C-atoms respectively. The final difference map was free of chemically significant features.

Figures

Fig. 1.

ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level.

Fig. 2.

Unit cell packing of (I) showing hydrogen bonding (dashed lines); H-atoms not involved in hydrogen bonding have been excluded for clarity.

Crystal data

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

Data collection

Nonius KappaCCD diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	1431 reflections with I > 2σ(I)
graphite	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

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

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
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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.82	2.658 (3)	177

Symmetry codes: (i) −x, −y−1, −z.