1-[4-(2-Chloro­eth­oxy)-2-hy­droxy­phen­yl]ethanone

Wang, L.; Jiao, S.; Shi, P.; Wei, G.-H.

doi:10.1107/S1600536810054632

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o461

doi:10.1107/S1600536810054632

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1-[4-(2-Chloroethoxy)-2-hydroxyphenyl]ethanone

Li Wang,^a Shuo Jiao,^a Peng Shi ^a and Ge-Hong Wei ^a ^*

^aCollege of Life Sciences, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China
^*Correspondence e-mail: weigehong@yahoo.com.cn

(Received 25 December 2010; accepted 29 December 2010; online 22 January 2011)

In the title compound, C₁₀H₁₁ClO₃, obtained by the reaction of 2,4-dihydroxyacetophenone, potassium carbonate and 1-bromo-2-chloroethane, an intramolecular O—H⋯O hydrogen bond occurs.

Related literature

The title compound was synthesized by the Williamson reaction (Dermer, 1934 ). For a related structure, see: Schlemper (1986 ).

Experimental

Crystal data

C₁₀H₁₁ClO₃
M_r = 214.64
Orthorhombic, P c a 2₁
a = 8.9970 (7) Å
b = 5.3258 (4) Å
c = 20.6307 (17) Å
V = 988.55 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.40 × 0.39 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.868, T_max = 0.931
4434 measured reflections
1664 independent reflections
1121 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.141
S = 1.07
1664 reflections
127 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 758 Friedel pairs
Flack parameter: 0.10 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.81	2.533 (5)	145

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054632/jh2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054632/jh2251Isup2.hkl

checkCIF report

Comment top

In this paper, we used the Williamson reaction (Dermer, 1934) to form the title compound, (I), which was synthesized by the reaction of 2,4-dihydroxyacetophenone, potassium carbonate and 1-bromo-2-chloroethane at 329 K. In (I)(Fig.1), the bond lengths and angles are normal and comparable to those observed in the related structure (Schlemper, 1986). The dihedral angle between the benzene ring C3—C8 and the plane O3C9C10 is 5.83 (4)°. There are no significantly short intermolecular contacts in the crystal lattice.

Related literature top

The title compound was synthesized by the Williamson reaction (Dermer, 1934). For a related structure, see: Schlemper (1986).

Experimental top

2, 4-Dihydroxylacetonephenone (5 mmol), potassium carbonate (6 mmol), 1-bromo-2-chloroethane (5 mmol), and 50 ml acetone were mixed in 100 ml flask. After 2.5 h stirring at 329 K, the crude product was obtained. The crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the title compound in n-hexane/ethyl acetate/methanol (3:3:1, V/V) at 283 K.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and displacement ellipsoids drawn at the 30% probability level.

1-[4-(2-Chloroethoxy)-2-hydroxyphenyl]ethanone top

Crystal data top

C₁₀H₁₁ClO₃	D_x = 1.442 Mg m⁻³
M_r = 214.64	Melting point = 375–376 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.9970 (7) Å	Cell parameters from 1122 reflections
b = 5.3258 (4) Å	θ = 3.8–21.7°
c = 20.6307 (17) Å	µ = 0.36 mm⁻¹
V = 988.55 (13) Å³	T = 298 K
Z = 4	Orthorhombic, colourless
F(000) = 448	0.40 × 0.39 × 0.20 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	1664 independent reflections
Radiation source: fine-focus sealed tube	1121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
phi and ω scans	θ_max = 25.0°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→8
T_min = 0.868, T_max = 0.931	k = −6→6
4434 measured reflections	l = −24→20

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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0604P)² + 0.0181P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1664 reflections	Δρ_max = 0.24 e Å⁻³
127 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 758 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (14)

Crystal data top

C₁₀H₁₁ClO₃	V = 988.55 (13) Å³
M_r = 214.64	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.9970 (7) Å	µ = 0.36 mm⁻¹
b = 5.3258 (4) Å	T = 298 K
c = 20.6307 (17) Å	0.40 × 0.39 × 0.20 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	1664 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1121 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.931	R_int = 0.063
4434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.141	Δρ_max = 0.24 e Å⁻³
S = 1.07	Δρ_min = −0.21 e Å⁻³
1664 reflections	Absolute structure: Flack (1983), 758 Friedel pairs
127 parameters	Absolute structure parameter: 0.10 (14)
1 restraint

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
Cl1	−0.15098 (17)	0.8043 (3)	0.62958 (8)	0.0704 (5)
O1	0.2660 (4)	0.6840 (7)	1.02143 (16)	0.0554 (10)
O2	0.1105 (4)	0.4294 (7)	0.94300 (15)	0.0518 (9)
H2	0.1390	0.4778	0.9786	0.078*
O3	0.1071 (4)	0.6890 (7)	0.72354 (16)	0.0560 (10)
C1	0.4075 (6)	1.0330 (9)	0.9931 (3)	0.0535 (14)
H1A	0.4253	1.0346	1.0390	0.080*
H1B	0.3628	1.1890	0.9803	0.080*
H1C	0.5000	1.0116	0.9706	0.080*
C2	0.3071 (5)	0.8247 (9)	0.9769 (2)	0.0399 (11)
C3	0.2555 (5)	0.7861 (9)	0.9118 (2)	0.0387 (11)
C4	0.1582 (5)	0.5869 (9)	0.8976 (2)	0.0384 (11)
C5	0.1058 (5)	0.5501 (9)	0.8351 (2)	0.0414 (12)
H5	0.0405	0.4190	0.8265	0.050*
C6	0.1495 (5)	0.7049 (9)	0.7863 (2)	0.0401 (12)
C7	0.2485 (6)	0.9076 (9)	0.7991 (3)	0.0480 (13)
H7	0.2794	1.0143	0.7660	0.058*
C8	0.2962 (5)	0.9404 (9)	0.8603 (2)	0.0451 (13)
H8	0.3599	1.0739	0.8687	0.054*
C9	0.0041 (6)	0.4949 (9)	0.7074 (2)	0.0518 (13)
H9A	−0.0826	0.5050	0.7352	0.062*
H9B	0.0499	0.3316	0.7133	0.062*
C10	−0.0399 (6)	0.5287 (9)	0.6389 (3)	0.0571 (14)
H10A	−0.0957	0.3831	0.6245	0.068*
H10B	0.0484	0.5425	0.6122	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0739 (9)	0.0668 (9)	0.0706 (9)	0.0068 (7)	−0.0081 (8)	0.0050 (10)
O1	0.065 (2)	0.055 (2)	0.046 (2)	−0.009 (2)	−0.0029 (19)	0.0086 (19)
O2	0.062 (2)	0.046 (2)	0.0474 (19)	−0.0151 (18)	−0.0008 (16)	0.0123 (17)
O3	0.061 (2)	0.063 (2)	0.044 (2)	−0.0216 (19)	−0.0055 (16)	0.0038 (19)
C1	0.049 (3)	0.051 (3)	0.061 (3)	0.002 (3)	−0.008 (3)	−0.007 (3)
C2	0.032 (2)	0.044 (3)	0.044 (3)	0.010 (2)	0.003 (2)	−0.004 (3)
C3	0.033 (2)	0.039 (3)	0.044 (3)	0.001 (2)	0.007 (2)	0.003 (2)
C4	0.039 (3)	0.038 (3)	0.039 (3)	0.009 (2)	0.003 (2)	0.006 (2)
C5	0.046 (3)	0.032 (3)	0.046 (3)	−0.003 (2)	0.001 (2)	0.003 (2)
C6	0.045 (3)	0.039 (3)	0.036 (3)	−0.001 (2)	0.002 (2)	−0.005 (2)
C7	0.050 (3)	0.038 (3)	0.056 (3)	−0.011 (2)	0.007 (3)	0.011 (3)
C8	0.043 (3)	0.040 (3)	0.052 (3)	−0.008 (2)	0.000 (2)	−0.002 (2)
C9	0.053 (3)	0.048 (3)	0.055 (3)	−0.003 (3)	−0.005 (3)	−0.001 (2)
C10	0.062 (3)	0.055 (3)	0.055 (3)	0.002 (3)	−0.001 (3)	−0.014 (3)

Geometric parameters (Å, º) top

Cl1—C10	1.787 (5)	C4—C5	1.387 (7)
O1—C2	1.242 (6)	C5—C6	1.359 (6)
O2—C4	1.329 (5)	C5—H5	0.9300
O2—H2	0.8200	C6—C7	1.425 (6)
O3—C6	1.352 (6)	C7—C8	1.344 (7)
O3—C9	1.428 (6)	C7—H7	0.9300
C1—C2	1.469 (7)	C8—H8	0.9300
C1—H1A	0.9600	C9—C10	1.477 (8)
C1—H1B	0.9600	C9—H9A	0.9700
C1—H1C	0.9600	C9—H9B	0.9700
C2—C3	1.436 (7)	C10—H10A	0.9700
C3—C8	1.392 (7)	C10—H10B	0.9700
C3—C4	1.407 (7)

C4—O2—H2	109.5	O3—C6—C7	113.7 (4)
C6—O3—C9	116.9 (4)	C5—C6—C7	120.2 (4)
C2—C1—H1A	109.5	C8—C7—C6	118.2 (5)
C2—C1—H1B	109.5	C8—C7—H7	120.9
H1A—C1—H1B	109.5	C6—C7—H7	120.9
C2—C1—H1C	109.5	C7—C8—C3	123.8 (5)
H1A—C1—H1C	109.5	C7—C8—H8	118.1
H1B—C1—H1C	109.5	C3—C8—H8	118.1
O1—C2—C3	120.6 (4)	O3—C9—C10	108.0 (4)
O1—C2—C1	118.1 (4)	O3—C9—H9A	110.1
C3—C2—C1	121.3 (5)	C10—C9—H9A	110.1
C8—C3—C4	116.7 (4)	O3—C9—H9B	110.1
C8—C3—C2	123.0 (5)	C10—C9—H9B	110.1
C4—C3—C2	120.3 (4)	H9A—C9—H9B	108.4
O2—C4—C5	117.2 (4)	C9—C10—Cl1	110.7 (4)
O2—C4—C3	122.0 (4)	C9—C10—H10A	109.5
C5—C4—C3	120.8 (4)	Cl1—C10—H10A	109.5
C6—C5—C4	120.3 (4)	C9—C10—H10B	109.5
C6—C5—H5	119.8	Cl1—C10—H10B	109.5
C4—C5—H5	119.8	H10A—C10—H10B	108.1
O3—C6—C5	126.1 (4)

O1—C2—C3—C8	179.0 (4)	C9—O3—C6—C7	−178.1 (4)
C1—C2—C3—C8	0.0 (7)	C4—C5—C6—O3	179.8 (4)
O1—C2—C3—C4	−0.4 (7)	C4—C5—C6—C7	−0.5 (7)
C1—C2—C3—C4	−179.3 (4)	O3—C6—C7—C8	179.5 (4)
C8—C3—C4—O2	−179.2 (4)	C5—C6—C7—C8	−0.2 (7)
C2—C3—C4—O2	0.2 (6)	C6—C7—C8—C3	0.7 (7)
C8—C3—C4—C5	−0.4 (6)	C4—C3—C8—C7	−0.4 (7)
C2—C3—C4—C5	179.0 (4)	C2—C3—C8—C7	−179.7 (4)
O2—C4—C5—C6	179.7 (4)	C6—O3—C9—C10	173.7 (4)
C3—C4—C5—C6	0.8 (7)	O3—C9—C10—Cl1	−69.2 (5)
C9—O3—C6—C5	1.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.81	2.533 (5)	145

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁ClO₃
M_r	214.64
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	8.9970 (7), 5.3258 (4), 20.6307 (17)
V (Å³)	988.55 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.40 × 0.39 × 0.20

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.868, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	4434, 1664, 1121
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.141, 1.07
No. of reflections	1664
No. of parameters	127
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21
Absolute structure	Flack (1983), 758 Friedel pairs
Absolute structure parameter	0.10 (14)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
O2—H2···O1	0.82	1.81	2.533 (5)	145

Acknowledgements

We would like to acknowledge funding support from the National Natural Science Foundation of China (grant No. 31070444).

References

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