3-(2-Chloro-phen-yl)-4-hy-droxy-furan-2(5H)-one.

In the title mol-ecule, C(10)H(7)ClO(3), 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 mol-ecules 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 = 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) 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[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

Δρmax = 0.32 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048641/pv2483sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048641/pv2483Isup2.hkl

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

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

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

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 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)

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
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)

	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)

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)

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.

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) .