3-(2,4-Di­chloro­phenyl)-1-(2-furyl)-3-hydroxy­propan-1-one

The title compound, C₁₃H₁₀Cl₂O₃, was synthesized by the Reformatsky reaction of 2,4-di­chloro­benz­aldehyde and 2-(bromo­acetyl)­furan in an aqueous medium. Two intermol­ecular O—H...O hydrogen bonds are formed between the hydroxy and carbonyl groups of two mol­ecules related by a center of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one

Crystal data

C13H10Cl2O3	Z = 2
Mr = 285.11	F(000) = 292
Triclinic, P1	Dx = 1.482 Mg m^−3
Hall symbol: -P 1	Melting point: 340 K
a = 7.933 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.737 (3) Å	Cell parameters from 989 reflections
c = 9.907 (3) Å	θ = 2.7–26.3°
α = 79.464 (4)°	µ = 0.50 mm^−1
β = 72.596 (4)°	T = 293 K
γ = 79.918 (5)°	Plate, colorless
V = 638.9 (3) Å^3	0.22 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2246 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ψ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.882, Tmax = 0.932	k = −10→9
3322 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 0.1932P] where P = (Fo^2 + 2Fc^2)/3
2246 reflections	(Δ/σ)max = 0.004
164 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.44 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	0.43230 (8)	0.14544 (9)	0.77489 (7)	0.0706 (3)
Cl2	−0.17314 (9)	−0.08303 (9)	0.84055 (8)	0.0758 (3)
O1	0.3100 (2)	0.46997 (19)	0.41418 (17)	0.0588 (4)
H1	0.2657	0.5367	0.4675	0.088*
O2	0.7640 (2)	0.3692 (2)	0.34604 (18)	0.0656 (5)
O3	0.8364 (2)	0.4239 (2)	0.05729 (18)	0.0687 (5)
C1	0.0880 (3)	0.2283 (3)	0.5397 (2)	0.0512 (6)
H1A	0.0737	0.2896	0.4557	0.061*
C2	−0.0390 (3)	0.1325 (3)	0.6170 (2)	0.0535 (6)
H2	−0.1371	0.1285	0.5854	0.064*
C3	−0.0178 (3)	0.0426 (3)	0.7423 (2)	0.0483 (5)
C4	0.1239 (3)	0.0486 (3)	0.7919 (2)	0.0466 (5)
H4	0.1356	−0.0109	0.8774	0.056*
C5	0.2496 (3)	0.1456 (3)	0.7117 (2)	0.0436 (5)
C6	0.2371 (3)	0.2358 (2)	0.5837 (2)	0.0411 (5)
C7	0.3811 (3)	0.3332 (3)	0.4909 (2)	0.0460 (5)
H7	0.4445	0.3635	0.5510	0.055*
C8	0.5123 (3)	0.2362 (3)	0.3812 (2)	0.0569 (6)
H8A	0.5584	0.1389	0.4304	0.068*
H8B	0.4503	0.2100	0.3194	0.068*
C9	0.6662 (3)	0.3234 (3)	0.2911 (2)	0.0499 (5)
C10	0.6960 (3)	0.3472 (3)	0.1375 (2)	0.0473 (5)
C11	0.6134 (3)	0.3081 (3)	0.0499 (3)	0.0561 (6)
H11	0.5142	0.2548	0.0773	0.067*
C12	0.7062 (4)	0.3635 (3)	−0.0913 (3)	0.0663 (7)
H12	0.6802	0.3541	−0.1747	0.080*
C13	0.8379 (4)	0.4317 (4)	−0.0811 (3)	0.0732 (8)
H13	0.9203	0.4788	−0.1586	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0547 (4)	0.1037 (6)	0.0590 (4)	−0.0306 (3)	−0.0275 (3)	0.0139 (3)
Cl2	0.0567 (4)	0.0902 (5)	0.0782 (5)	−0.0356 (4)	−0.0115 (3)	0.0075 (4)
O1	0.0757 (12)	0.0515 (9)	0.0461 (9)	−0.0115 (8)	−0.0158 (8)	0.0025 (7)
O2	0.0646 (11)	0.0862 (13)	0.0510 (10)	−0.0243 (10)	−0.0096 (8)	−0.0190 (9)
O3	0.0678 (11)	0.0902 (13)	0.0469 (10)	−0.0369 (10)	−0.0017 (8)	−0.0050 (9)
C1	0.0560 (13)	0.0611 (14)	0.0385 (11)	−0.0097 (11)	−0.0174 (10)	−0.0021 (10)
C2	0.0459 (13)	0.0686 (15)	0.0513 (13)	−0.0121 (11)	−0.0169 (10)	−0.0114 (11)
C3	0.0392 (11)	0.0540 (13)	0.0493 (13)	−0.0106 (10)	−0.0058 (10)	−0.0077 (10)
C4	0.0426 (12)	0.0525 (13)	0.0406 (11)	−0.0061 (10)	−0.0090 (9)	0.0001 (9)
C5	0.0381 (11)	0.0533 (12)	0.0400 (11)	−0.0065 (9)	−0.0112 (9)	−0.0064 (9)
C6	0.0451 (11)	0.0448 (11)	0.0330 (10)	−0.0075 (9)	−0.0074 (9)	−0.0083 (9)
C7	0.0539 (13)	0.0489 (12)	0.0350 (11)	−0.0139 (10)	−0.0086 (9)	−0.0048 (9)
C8	0.0634 (15)	0.0554 (14)	0.0474 (13)	−0.0200 (12)	0.0018 (11)	−0.0127 (11)
C9	0.0507 (13)	0.0507 (13)	0.0460 (12)	−0.0087 (10)	−0.0045 (10)	−0.0137 (10)
C10	0.0466 (12)	0.0481 (12)	0.0439 (12)	−0.0109 (10)	−0.0046 (10)	−0.0063 (10)
C11	0.0556 (14)	0.0597 (14)	0.0545 (14)	−0.0095 (11)	−0.0147 (11)	−0.0105 (11)
C12	0.0792 (19)	0.0743 (18)	0.0461 (14)	−0.0050 (15)	−0.0202 (13)	−0.0096 (12)
C13	0.084 (2)	0.085 (2)	0.0413 (14)	−0.0208 (16)	−0.0020 (13)	−0.0025 (13)

Geometric parameters (Å, º)

Cl1—C5	1.742 (2)	C5—C6	1.386 (3)
Cl2—C3	1.743 (2)	C6—C7	1.516 (3)
O1—C7	1.418 (3)	C7—C8	1.528 (3)
O1—H1	0.8200	C7—H7	0.9800
O2—C9	1.224 (3)	C8—C9	1.514 (3)
O3—C13	1.357 (3)	C8—H8A	0.9700
O3—C10	1.363 (3)	C8—H8B	0.9700
C1—C2	1.379 (3)	C9—C10	1.449 (3)
C1—C6	1.393 (3)	C10—C11	1.352 (3)
C1—H1A	0.9300	C11—C12	1.412 (4)
C2—C3	1.381 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.326 (4)
C3—C4	1.367 (3)	C12—H12	0.9300
C4—C5	1.386 (3)	C13—H13	0.9300
C4—H4	0.9300
C7—O1—H1	109.5	C6—C7—H7	109.4
C13—O3—C10	106.5 (2)	C8—C7—H7	109.4
C2—C1—C6	121.9 (2)	C9—C8—C7	111.98 (18)
C2—C1—H1A	119.0	C9—C8—H8A	109.2
C6—C1—H1A	119.0	C7—C8—H8A	109.2
C1—C2—C3	118.8 (2)	C9—C8—H8B	109.2
C1—C2—H2	120.6	C7—C8—H8B	109.2
C3—C2—H2	120.6	H8A—C8—H8B	107.9
C4—C3—C2	121.6 (2)	O2—C9—C10	121.3 (2)
C4—C3—Cl2	118.45 (17)	O2—C9—C8	121.1 (2)
C2—C3—Cl2	119.98 (17)	C10—C9—C8	117.6 (2)
C3—C4—C5	118.3 (2)	C11—C10—O3	109.1 (2)
C3—C4—H4	120.8	C11—C10—C9	133.8 (2)
C5—C4—H4	120.8	O3—C10—C9	117.1 (2)
C6—C5—C4	122.57 (19)	C10—C11—C12	107.1 (2)
C6—C5—Cl1	120.29 (16)	C10—C11—H11	126.5
C4—C5—Cl1	117.11 (16)	C12—C11—H11	126.5
C5—C6—C1	116.80 (19)	C13—C12—C11	106.2 (2)
C5—C6—C7	122.51 (19)	C13—C12—H12	126.9
C1—C6—C7	120.63 (18)	C11—C12—H12	126.9
O1—C7—C6	111.93 (18)	C12—C13—O3	111.1 (2)
O1—C7—C8	107.32 (18)	C12—C13—H13	124.4
C6—C7—C8	109.40 (17)	O3—C13—H13	124.4
O1—C7—H7	109.4
C6—C1—C2—C3	0.5 (4)	C1—C6—C7—C8	−85.0 (3)
C1—C2—C3—C4	1.1 (4)	O1—C7—C8—C9	62.0 (3)
C1—C2—C3—Cl2	−178.54 (17)	C6—C7—C8—C9	−176.37 (19)
C2—C3—C4—C5	−1.3 (3)	C7—C8—C9—O2	58.6 (3)
Cl2—C3—C4—C5	178.37 (16)	C7—C8—C9—C10	−122.8 (2)
C3—C4—C5—C6	−0.1 (3)	C13—O3—C10—C11	0.3 (3)
C3—C4—C5—Cl1	−177.88 (17)	C13—O3—C10—C9	179.8 (2)
C4—C5—C6—C1	1.6 (3)	O2—C9—C10—C11	178.9 (3)
Cl1—C5—C6—C1	179.31 (16)	C8—C9—C10—C11	0.3 (4)
C4—C5—C6—C7	−175.64 (19)	O2—C9—C10—O3	−0.5 (3)
Cl1—C5—C6—C7	2.0 (3)	C8—C9—C10—O3	−179.1 (2)
C2—C1—C6—C5	−1.8 (3)	O3—C10—C11—C12	−0.2 (3)
C2—C1—C6—C7	175.5 (2)	C9—C10—C11—C12	−179.7 (3)
C5—C6—C7—O1	−149.0 (2)	C10—C11—C12—C13	0.1 (3)
C1—C6—C7—O1	33.8 (3)	C11—C12—C13—O3	0.1 (3)
C5—C6—C7—C8	92.2 (2)	C10—O3—C13—C12	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.09	2.839 (3)	152
C7—H7···Cl1	0.98	2.64	3.088 (2)	108
C12—H12···O1^ii	0.93	2.57	3.293 (3)	135

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.