3-(2-Chloro­phen­yl)-4-hy­droxy­furan-2(5H)-one

Abstract

In the title mol­ecule, C₁₀H₇ClO₃, the butyrolactone core, a furan-2(5H)-one, forms a dihedral angle of 59.21 (5)° with the benzene ring. In the crystal, two types of hydrogen bonds (O—H⋯O and C—H⋯Cl) link mol­ecules into infinite chains along the b axis. π–π contacts [centroid–centroid distances = 3.6359 (10) and 3.8776 (11) Å] link the chains into a three-dimensional network.

Related literature

For the anti­bacterial activity of furan­ones, see: Xiao et al. (2011 ▶). For related structures, see: Peng et al. (2011 ▶); Xiao et al. (2010 ▶).

Experimental

Crystal data

• C₁₀H₇ClO₃

• M _r = 210.61

• Monoclinic,

• a = 9.9699 (15) Å

• b = 11.8308 (18) Å

• c = 8.1562 (12) Å

• β = 104.898 (2)°

• V = 929.7 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.39 mm⁻¹

• T = 296 K

• 0.30 × 0.20 × 0.20 mm

Data collection

• Bruker SMART APEX CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.893, T _max = 0.927

• 7259 measured reflections

• 2240 independent reflections

• 2037 reflections with I > 2σ(I)

• R _int = 0.018

Refinement

• R[F ² > 2σ(F ²)] = 0.034

• wR(F ²) = 0.108

• S = 1.12

• 2240 reflections

• 132 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.32 e Å⁻³

• Δρ_min = −0.33 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811048641/pv2483Isup3.cml

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
O3—H3⋯O1i	0.82 (3)	1.80 (3)	2.6182 (16)	170 (3)
C9—H9B⋯Cl1i	0.97	2.77	3.7126 (16)	165

Symmetry code: (i) .

supplementary crystallographic information

Comment

Recently, we have reported the antibacterial activities of a few γ-butyrolactones (furanones) (Xiao et al., 2011). As a part of our ongoing studies of γ-butyrolactones (Xiao et al., 2010), we herein report the crystal structure of the title compound.

In the title compound (Fig. 1), the butyrolactone moiety makes a dihedral angle of 59.21 (5) ° with the benzene ring. Relatively strong intermolecular hydrogen bonds (O—H···O) link molecules into an infinite chain running along the b axis, which is further consolidated by weak intermolecular C—H···Cl interactions. There are π–π contacts between benzene rings and butyrolactone rings with centroid–centroid distances 3.6359 (10) and 3.8776 (11) Å, respectively (Fig. 2). The molecular dimensions in the title molecule agree very well with the corresponding molecular dimensions reported in a few similar structures (Peng et al., 2011; Xiao et al., 2010).

Experimental

A dropwise solution of 2-ethoxy-2-oxoethyl 2-(2-chlorophenyl)acetate (1.03 g, 4 mmol) in dry THF was added to a suspension of NaH in dry THF in an ice cold bath. The stirring was maintained at room temperature for 6 h. Water was added and the solution was extracted twice with ethyl ether. The aqueous phase was cooled to 273 K and then acidified with concentrated hydrochloric acid to give a solid precipitate. The title compound thus obtained was crystallized from ethanol-water (2:1) to give the colorless blocks suitable for single-crystal structure determination.

Refinement

The H-atoms bonded to C-atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.93 and 0.97 Å for aryl and methylene type H atoms, respectively, with U_iso(H) = 1.2 U_eq(C). The hydroxyl H atom was located from a difference Fourier map and was allowed to refine freely.

Figures

Fig. 1.

Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2.

A unit cell packing diagram of the title compound showing a three-dimensional network built through intermolecular hydrogen bonds and π–π contacts.

Fig. 3.

A unit cell packing diagram of the title compound

Crystal data

C10H7ClO3	F(000) = 432
Mr = 210.61	Dx = 1.505 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2125 reflections
a = 9.9699 (15) Å	θ = 2.7–27.8°
b = 11.8308 (18) Å	µ = 0.39 mm−1
c = 8.1562 (12) Å	T = 296 K
β = 104.898 (2)°	Block, colorless
V = 929.7 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	2240 independent reflections
Radiation source: fine-focus sealed tube	2037 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scan	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
Tmin = 0.893, Tmax = 0.927	k = −15→15
7259 measured reflections	l = −10→10

Refinement

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
2240 reflections	Δρmax = 0.32 e Å−3
132 parameters	Δρmin = −0.33 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (4)

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
C1	0.70093 (13)	0.46964 (11)	0.22948 (16)	0.0334 (3)
C2	0.62894 (13)	0.38058 (11)	0.13494 (17)	0.0350 (3)
C3	0.48970 (15)	0.36149 (14)	0.1245 (2)	0.0475 (4)
H3A	0.4435	0.3010	0.0617	0.057*
C4	0.42063 (16)	0.43319 (17)	0.2082 (2)	0.0567 (4)
H4	0.3274	0.4206	0.2022	0.068*
C5	0.48850 (17)	0.52330 (17)	0.3006 (2)	0.0556 (4)
H5	0.4408	0.5719	0.3553	0.067*
C6	0.62747 (16)	0.54126 (14)	0.3117 (2)	0.0455 (3)
H6	0.6729	0.6019	0.3748	0.055*
C7	0.84833 (13)	0.49225 (10)	0.23989 (17)	0.0337 (3)
C8	0.96157 (13)	0.41569 (11)	0.31055 (18)	0.0365 (3)
C9	1.05960 (15)	0.57272 (12)	0.2315 (2)	0.0459 (3)
H9A	1.0901	0.5790	0.1281	0.055*
H9B	1.1076	0.6290	0.3119	0.055*
C10	0.90647 (14)	0.58691 (11)	0.19598 (18)	0.0380 (3)
Cl1	0.71082 (4)	0.29321 (3)	0.01933 (5)	0.04628 (15)
H3	0.897 (3)	0.730 (2)	0.125 (3)	0.080 (7)*
O1	0.95949 (11)	0.32284 (8)	0.37570 (15)	0.0465 (3)
O2	1.08432 (10)	0.46088 (9)	0.30186 (16)	0.0482 (3)
O3	0.84132 (12)	0.67963 (10)	0.12899 (18)	0.0564 (3)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0298 (6)	0.0325 (6)	0.0387 (6)	0.0021 (4)	0.0102 (5)	0.0046 (5)
C2	0.0319 (6)	0.0325 (6)	0.0400 (6)	0.0003 (5)	0.0082 (5)	0.0070 (5)
C3	0.0328 (7)	0.0490 (8)	0.0568 (9)	−0.0059 (6)	0.0046 (6)	0.0136 (7)
C4	0.0296 (7)	0.0776 (12)	0.0647 (10)	0.0058 (7)	0.0156 (7)	0.0213 (9)
C5	0.0430 (8)	0.0773 (12)	0.0514 (9)	0.0217 (8)	0.0208 (7)	0.0107 (8)
C6	0.0417 (7)	0.0505 (8)	0.0454 (7)	0.0105 (6)	0.0128 (6)	−0.0012 (6)
C7	0.0306 (6)	0.0290 (6)	0.0419 (6)	−0.0011 (4)	0.0101 (5)	−0.0033 (5)
C8	0.0318 (6)	0.0314 (6)	0.0470 (7)	0.0004 (5)	0.0117 (5)	−0.0048 (5)
C9	0.0356 (7)	0.0384 (7)	0.0648 (9)	−0.0071 (5)	0.0149 (6)	−0.0014 (6)
C10	0.0345 (6)	0.0311 (6)	0.0469 (7)	−0.0040 (5)	0.0080 (5)	−0.0031 (5)
Cl1	0.0483 (2)	0.0362 (2)	0.0521 (2)	0.00220 (13)	0.00863 (16)	−0.00722 (13)
O1	0.0408 (5)	0.0334 (5)	0.0656 (7)	0.0049 (4)	0.0140 (5)	0.0054 (4)
O2	0.0304 (5)	0.0397 (5)	0.0752 (7)	0.0007 (4)	0.0146 (5)	0.0014 (5)
O3	0.0410 (6)	0.0344 (5)	0.0876 (9)	−0.0053 (4)	0.0056 (6)	0.0141 (6)

Geometric parameters (Å, °)

C1—C2	1.3912 (18)	C6—H6	0.9300
C1—C6	1.3987 (19)	C7—C10	1.3510 (18)
C1—C7	1.4745 (17)	C7—C8	1.4465 (17)
C2—C3	1.3873 (19)	C8—O1	1.2228 (17)
C2—Cl1	1.7377 (14)	C8—O2	1.3539 (16)
C3—C4	1.379 (3)	C9—O2	1.4382 (18)
C3—H3A	0.9300	C9—C10	1.488 (2)
C4—C5	1.378 (3)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C5—C6	1.381 (2)	C10—O3	1.3195 (17)
C5—H5	0.9300	O3—H3	0.82 (3)
C2—C1—C6	117.73 (12)	C10—C7—C8	106.29 (11)
C2—C1—C7	122.26 (11)	C10—C7—C1	128.63 (12)
C6—C1—C7	119.97 (12)	C8—C7—C1	125.00 (11)
C3—C2—C1	121.53 (13)	O1—C8—O2	119.61 (12)
C3—C2—Cl1	118.17 (11)	O1—C8—C7	129.56 (12)
C1—C2—Cl1	120.26 (10)	O2—C8—C7	110.81 (11)
C4—C3—C2	119.25 (15)	O2—C9—C10	104.08 (11)
C4—C3—H3A	120.4	O2—C9—H9A	110.9
C2—C3—H3A	120.4	C10—C9—H9A	110.9
C5—C4—C3	120.60 (14)	O2—C9—H9B	110.9
C5—C4—H4	119.7	C10—C9—H9B	110.9
C3—C4—H4	119.7	H9A—C9—H9B	109.0
C4—C5—C6	119.86 (15)	O3—C10—C7	126.86 (13)
C4—C5—H5	120.1	O3—C10—C9	123.04 (12)
C6—C5—H5	120.1	C7—C10—C9	110.09 (12)
C5—C6—C1	121.02 (16)	C8—O2—C9	108.65 (10)
C5—C6—H6	119.5	C10—O3—H3	111.0 (18)
C1—C6—H6	119.5
C6—C1—C2—C3	−1.21 (19)	C6—C1—C7—C8	119.84 (15)
C7—C1—C2—C3	−179.04 (12)	C10—C7—C8—O1	175.41 (15)
C6—C1—C2—Cl1	176.21 (10)	C1—C7—C8—O1	−1.6 (2)
C7—C1—C2—Cl1	−1.61 (17)	C10—C7—C8—O2	−2.92 (16)
C1—C2—C3—C4	0.7 (2)	C1—C7—C8—O2	−179.92 (12)
Cl1—C2—C3—C4	−176.74 (12)	C8—C7—C10—O3	−178.86 (15)
C2—C3—C4—C5	0.4 (2)	C1—C7—C10—O3	−2.0 (2)
C3—C4—C5—C6	−0.9 (3)	C8—C7—C10—C9	2.03 (16)
C4—C5—C6—C1	0.4 (2)	C1—C7—C10—C9	178.90 (13)
C2—C1—C6—C5	0.6 (2)	O2—C9—C10—O3	−179.72 (14)
C7—C1—C6—C5	178.52 (14)	O2—C9—C10—C7	−0.57 (17)
C2—C1—C7—C10	121.29 (16)	O1—C8—O2—C9	−175.94 (13)
C6—C1—C7—C10	−56.5 (2)	C7—C8—O2—C9	2.58 (16)
C2—C1—C7—C8	−62.39 (19)	C10—C9—O2—C8	−1.25 (16)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.82 (3)	1.80 (3)	2.6182 (16)	170 (3)
C9—H9B···Cl1i	0.97	2.77	3.7126 (16)	165.

Symmetry codes: (i) −x+2, y+1/2, −z+1/2.