1-[4-(3-Chloro-prop-oxy)-2-hydroxy-phen-yl]ethanone.

The title compound, C(11)H(13)ClO(3), has been obtained in the reaction of 2, 4-dihydroxy-lacetonephenone, potassium carbonate and 1-bromo-3-chloro-hexane. The hydr-oxy group is involved in an intra-molecular O-H⋯O hydrogen bond. The crystal packing exhibits no significantly short inter-molecular contacts.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ▶). For a related structure, see: Schlemper (1986 ▶).

Experimental

Crystal data

C11H13ClO3

M = 228.66

Orthorhombic,

a = 18.620 (2) Å

b = 11.963 (11) Å

c = 5.0240 (6) Å

V = 1119.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 298 K

0.49 × 0.44 × 0.43 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.857, T max = 0.873

4851 measured reflections

1946 independent reflections

1556 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.103

S = 1.03

1946 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 761 Friedel pairs

Flack parameter: −0.16 (10)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051411/cv2661sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051411/cv2661Isup2.hkl

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

C11H13ClO3	Dx = 1.357 Mg m−3
Mr = 228.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 1957 reflections
a = 18.620 (2) Å	θ = 2.2–25.7°
b = 11.963 (11) Å	µ = 0.33 mm−1
c = 5.0240 (6) Å	T = 298 K
V = 1119.1 (11) Å3	Block, colourless
Z = 4	0.49 × 0.44 × 0.43 mm
F(000) = 480

Bruker Smart APEX CCD area-detector diffractometer	1946 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
graphite	Rint = 0.054
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→22
Tmin = 0.857, Tmax = 0.873	k = −9→14
4851 measured reflections	l = −5→5

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.0435P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1946 reflections	Δρmax = 0.22 e Å−3
138 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.16 (10)

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
O3	0.61841 (8)	0.94594 (14)	−0.1602 (4)	0.0460 (5)
O1	0.81896 (9)	1.15126 (15)	0.7343 (4)	0.0551 (6)
O2	0.70120 (10)	1.19429 (14)	0.4881 (5)	0.0556 (6)
H2	0.7320	1.2012	0.6036	0.083*
Cl1	0.48481 (5)	0.70010 (7)	−0.1232 (2)	0.0753 (3)
C1	0.89472 (15)	0.9967 (2)	0.6420 (7)	0.0592 (8)
H1A	0.9204	1.0254	0.7930	0.089*
H1B	0.9250	0.9996	0.4875	0.089*
H1C	0.8809	0.9207	0.6755	0.089*
C2	0.82884 (13)	1.0662 (2)	0.5953 (6)	0.0419 (6)
C3	0.77663 (12)	1.03407 (19)	0.3905 (6)	0.0356 (6)
C4	0.71379 (12)	1.09934 (19)	0.3463 (6)	0.0387 (6)
C5	0.66330 (12)	1.06801 (19)	0.1590 (6)	0.0412 (6)
H5	0.6227	1.1119	0.1321	0.049*
C6	0.67293 (12)	0.97085 (19)	0.0103 (6)	0.0363 (6)
C7	0.73511 (12)	0.9060 (2)	0.0441 (6)	0.0380 (6)
H7	0.7426	0.8424	−0.0586	0.046*
C8	0.78500 (13)	0.93830 (19)	0.2325 (6)	0.0385 (6)
H8	0.8259	0.8947	0.2555	0.046*
C9	0.62364 (13)	0.8441 (2)	−0.3163 (6)	0.0445 (7)
H9A	0.6283	0.7797	−0.2001	0.053*
H9B	0.6653	0.8470	−0.4320	0.053*
C10	0.55550 (14)	0.8356 (2)	−0.4797 (6)	0.0506 (7)
H10A	0.5519	0.9012	−0.5923	0.061*
H10B	0.5591	0.7709	−0.5953	0.061*
C11	0.48784 (15)	0.8259 (2)	−0.3180 (7)	0.0575 (8)
H11A	0.4468	0.8274	−0.4368	0.069*
H11B	0.4843	0.8899	−0.2002	0.069*

	U11	U22	U33	U12	U13	U23
O3	0.0445 (9)	0.0458 (10)	0.0476 (13)	0.0035 (8)	−0.0070 (9)	−0.0095 (10)
O1	0.0589 (12)	0.0490 (11)	0.0575 (14)	−0.0072 (9)	−0.0084 (11)	−0.0082 (11)
O2	0.0588 (12)	0.0425 (10)	0.0654 (16)	0.0090 (9)	−0.0098 (11)	−0.0183 (10)
Cl1	0.0772 (5)	0.0724 (5)	0.0764 (7)	−0.0267 (4)	−0.0077 (5)	0.0137 (6)
C1	0.0450 (16)	0.0682 (18)	0.064 (2)	0.0023 (12)	−0.0129 (17)	−0.005 (2)
C2	0.0448 (13)	0.0394 (14)	0.0414 (18)	−0.0095 (11)	−0.0003 (12)	0.0055 (14)
C3	0.0362 (12)	0.0317 (12)	0.0389 (16)	−0.0042 (10)	0.0019 (12)	0.0060 (12)
C4	0.0444 (13)	0.0289 (11)	0.0427 (18)	−0.0007 (11)	0.0035 (13)	−0.0005 (14)
C5	0.0403 (13)	0.0369 (13)	0.0463 (18)	0.0063 (10)	−0.0026 (13)	−0.0026 (13)
C6	0.0392 (13)	0.0358 (14)	0.0338 (15)	−0.0029 (11)	0.0041 (12)	0.0016 (11)
C7	0.0449 (14)	0.0301 (13)	0.0389 (18)	0.0003 (11)	0.0053 (12)	−0.0023 (12)
C8	0.0390 (13)	0.0312 (13)	0.0454 (18)	0.0021 (10)	0.0023 (12)	0.0052 (13)
C9	0.0467 (14)	0.0460 (14)	0.0408 (18)	−0.0031 (11)	0.0053 (13)	−0.0104 (14)
C10	0.0570 (16)	0.0529 (17)	0.0418 (18)	−0.0021 (13)	−0.0083 (14)	−0.0059 (15)
C11	0.0468 (15)	0.0565 (17)	0.069 (2)	−0.0035 (12)	−0.0072 (16)	0.0020 (16)

O3—C6	1.361 (3)	C5—C6	1.393 (3)
O3—C9	1.452 (3)	C5—H5	0.9300
O1—C2	1.248 (3)	C6—C7	1.404 (3)
O2—C4	1.361 (3)	C7—C8	1.381 (4)
O2—H2	0.8200	C7—H7	0.9300
Cl1—C11	1.796 (3)	C8—H8	0.9300
C1—C2	1.500 (4)	C9—C10	1.515 (4)
C1—H1A	0.9600	C9—H9A	0.9700
C1—H1B	0.9600	C9—H9B	0.9700
C1—H1C	0.9600	C10—C11	1.504 (4)
C2—C3	1.467 (4)	C10—H10A	0.9700
C3—C8	1.402 (4)	C10—H10B	0.9700
C3—C4	1.424 (3)	C11—H11A	0.9700
C4—C5	1.382 (3)	C11—H11B	0.9700
C6—O3—C9	118.25 (18)	C8—C7—H7	120.5
C4—O2—H2	109.5	C6—C7—H7	120.5
C2—C1—H1A	109.5	C7—C8—C3	122.8 (2)
C2—C1—H1B	109.5	C7—C8—H8	118.6
H1A—C1—H1B	109.5	C3—C8—H8	118.6
C2—C1—H1C	109.5	O3—C9—C10	107.02 (19)
H1A—C1—H1C	109.5	O3—C9—H9A	110.3
H1B—C1—H1C	109.5	C10—C9—H9A	110.3
O1—C2—C3	120.6 (2)	O3—C9—H9B	110.3
O1—C2—C1	119.0 (3)	C10—C9—H9B	110.3
C3—C2—C1	120.4 (2)	H9A—C9—H9B	108.6
C8—C3—C4	116.8 (2)	C11—C10—C9	114.5 (2)
C8—C3—C2	122.5 (2)	C11—C10—H10A	108.6
C4—C3—C2	120.7 (2)	C9—C10—H10A	108.6
O2—C4—C5	117.7 (2)	C11—C10—H10B	108.6
O2—C4—C3	121.2 (2)	C9—C10—H10B	108.6
C5—C4—C3	121.1 (2)	H10A—C10—H10B	107.6
C4—C5—C6	120.3 (2)	C10—C11—Cl1	112.67 (19)
C4—C5—H5	119.9	C10—C11—H11A	109.1
C6—C5—H5	119.9	Cl1—C11—H11A	109.1
O3—C6—C5	115.1 (2)	C10—C11—H11B	109.1
O3—C6—C7	124.8 (2)	Cl1—C11—H11B	109.1
C5—C6—C7	120.1 (2)	H11A—C11—H11B	107.8
C8—C7—C6	118.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.85	2.570 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.85	2.570 (3)	146