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

Xiao, Z.-P.; Yi, L.-C.; Li, J.-L.; Xiang, K.-S.; Zhang, B.

doi:10.1107/S1600536811048641

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3428

https://doi.org/10.1107/S1600536811048641

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

Zhu-Ping Xiao,^a ^* Li-Cheng Yi,^a Jia-Liang Li,^a Kai-Shuang Xiang ^a and Bo Zhang ^a

^aThe Key Laboratory of Hunan Forest Products & Chemical Industry Engineering of Hunan Province and College of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
^*Correspondence e-mail: xiaozhuping2005@163.com

(Received 8 November 2011; accepted 15 November 2011; online 25 November 2011)

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, P 2₁ /c
a = 9.9699 (15) Å
b = 11.8308 (18) Å
c = 8.1562 (12) Å
β = 104.898 (2)°
V = 929.7 (2) Å³
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[F² > 2σ(F²)] = 0.034
wR(F²) = 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

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) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048641/pv2483sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048641/pv2483Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048641/pv2483Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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

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

Crystal data top

C₁₀H₇ClO₃	F(000) = 432
M_r = 210.61	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0607P)² + 0.1971P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
2240 reflections	Δρ_max = 0.32 e Å⁻³
132 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₇ClO₃	V = 929.7 (2) Å³
M_r = 210.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9699 (15) Å	µ = 0.39 mm⁻¹
b = 11.8308 (18) Å	T = 296 K
c = 8.1562 (12) Å	0.30 × 0.20 × 0.20 mm
β = 104.898 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	2240 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2037 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.927	R_int = 0.018
7259 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.32 e Å⁻³
2240 reflections	Δρ_min = −0.33 e Å⁻³
132 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₇ClO₃
M_r	210.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.9699 (15), 11.8308 (18), 8.1562 (12)
β (°)	104.898 (2)
V (Å³)	929.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.893, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	7259, 2240, 2037
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.108, 1.12
No. of reflections	2240
No. of parameters	132
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	164.5

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

Acknowledgements

The work was financed by the Planned Science and Technology Project of Hunan Province, China (grant No. 2011 F J3056), the Key Laboratory of Plant Resources Conservation and Utilization (Jishou University), College of Hunan Province (grant No. JSK201106) and Hunan Provincial Natural Science Foundation of China (grant No. 11 J J3113).

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