1-[4-(3-Chloro­prop­oxy)-2-hydroxy­phen­yl]ethanone

Ma, Y.-T.; Wang, J.-J.; Liu, X.-W.; Yang, S.-X.; Gao, J.-M.

doi:10.1107/S1600536809051411

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o52

doi:10.1107/S1600536809051411

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1-[4-(3-Chloropropoxy)-2-hydroxyphenyl]ethanone

Ya-Tuan Ma,^a,^b Jing-Jing Wang,^b Xi-Wang Liu,^b Sheng-Xiang Yang ^b and Jin-Ming Gao ^b ^*

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

(Received 17 November 2009; accepted 28 November 2009; online 4 December 2009)

The title compound, C₁₁H₁₃ClO₃, has been obtained in the reaction of 2, 4-dihydroxylacetonephenone, potassium carbonate and 1-bromo-3-chloro-hexane. The hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond. The crystal packing exhibits no significantly short intermolecular 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_r = 228.66
Orthorhombic, P 2₁ 2₁ 2
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.103
S = 1.03
1946 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 761 Friedel pairs
Flack parameter: −0.16 (10)

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

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/S1600536809051411/cv2661sup1.cif

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

checkCIF report

Comment top

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the employment of an alkali-metal salt of the hydroxy compound and an alkylhalide (Dermer, 1934).

In this paper, we present the title compound, (I), which was synthesized by the reaction of 2, 4-dihydroxylacetonephenone, potassium carbonate and 1-bromo-3-chloro-hexane. 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 3.82 (4)°. The crystal packing exhibits no significantly short intermolecular contacts

Related literature top

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

Experimental top

2, 4-Dihydroxylacetonephenone (3 mmol), potassium carbonate (6 mmol), 1-bromo-3-chloro-hexane (3 mmol), and 10 ml acetone were mixed in 50 ml flask. After 4 h stirring at 373 K, the crude product was obtained. The crystals were obtained by recrystallization from n-hexane/ethyl acetate. Elemental analysis: calculated for C₁₁H₁₃ClO₃: C 55.96, H 5.17%; found: C 55.88, H 5.25,%.

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 atomic numbering and 30% probability displacement ellipsoids.

1-[4-(3-Chloropropoxy)-2-hydroxyphenyl]ethanone top

Crystal data top

C₁₁H₁₃ClO₃	D_x = 1.357 Mg m⁻³
M_r = 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

Data collection top

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

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0468P)² + 0.0435P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1946 reflections	Δρ_max = 0.22 e Å⁻³
138 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 761 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.16 (10)

Crystal data top

C₁₁H₁₃ClO₃	V = 1119.1 (11) Å³
M_r = 228.66	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 18.620 (2) Å	µ = 0.33 mm⁻¹
b = 11.963 (11) Å	T = 298 K
c = 5.0240 (6) Å	0.49 × 0.44 × 0.43 mm

Data collection top

Bruker Smart APEX CCD area-detector diffractometer	1946 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1556 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.873	R_int = 0.054
4851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.103	Δρ_max = 0.22 e Å⁻³
S = 1.03	Δρ_min = −0.19 e Å⁻³
1946 reflections	Absolute structure: Flack (1983), 761 Friedel pairs
138 parameters	Absolute structure parameter: −0.16 (10)
0 restraints

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃ClO₃
M_r	228.66
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	298
a, b, c (Å)	18.620 (2), 11.963 (11), 5.0240 (6)
V (Å³)	1119.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.49 × 0.44 × 0.43

Data collection
Diffractometer	Bruker Smart APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.857, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	4851, 1946, 1556
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.103, 1.03
No. of reflections	1946
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19
Absolute structure	Flack (1983), 761 Friedel pairs
Absolute structure parameter	−0.16 (10)

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	1.85	2.570 (3)	146.4

Acknowledgements

The authors acknowledge the support of the Foundation of Northwest A&F University.

References

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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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