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

Wang, L.; Zhan, J.-P.; Liang, J.-Q.; Li, Z.-F.; Wei, G.-H.

doi:10.1107/S1600536811002169

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o462

doi:10.1107/S1600536811002169

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

Li Wang,^a Jun-Peng Zhan,^a Jian-Qiang Liang,^a Zhe-Fei Li ^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 14 January 2011; online 22 January 2011)

In the title compound, C₁₂H₁₅ClO₃, the ethoxy group is nearly coplanar with the benzene ring, making a dihedral angle of 9.03 (4)°, and is involved in an intramolecular O—H⋯O hydrogen bond to the neighbouring hydroxy group.

Related literature

For the synthesis of the title comppund, see: Dermer (1934 ). For related structures, see: Schlemper (1986 ).

Experimental

Crystal data

C₁₂H₁₅ClO₃
M_r = 242.69
Triclinic, $[P \overline 1]$
a = 5.2750 (4) Å
b = 9.8941 (10) Å
c = 11.6529 (12) Å
α = 99.735 (2)°
β = 98.242 (1)°
γ = 92.248 (1)°
V = 591.97 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.49 × 0.40 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.862, T_max = 0.929
3097 measured reflections
2068 independent reflections
1517 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.06
2068 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.82	2.539 (2)	146

Data collection: SMART (Bruker, 1996 ); cell refinement: SAINT (Bruker, 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/S1600536811002169/nc2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002169/nc2215Isup2.hkl

checkCIF report

Comment top

The crystal structure of the title compound was determined as a part of a project on the synthesis of new acetophenone derivatives. To clearly identify the product a single crystal X-ray analysis was performed.

In the crystal structure of the title compound the dihedral angle between the benzene ring C3—C8 and the ethoxy group is (O3, C9 and C10) amount to 9.03 (4)°. The carbonyl oxygen atom is involved in intramolecular O—H···O hydrogen bonding to the neighbored hydroxy group

Related literature top

For the synthesis of the title comppund, see: Dermer (1934). For related structures, see: Schlemper (1986).

Experimental top

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

Computing details top

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 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. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.

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

Crystal data top

C₁₂H₁₅ClO₃	F(000) = 256
M_r = 242.69	D_x = 1.362 Mg m⁻³
Triclinic, P1	Melting point = 317–318 K
a = 5.2750 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8941 (10) Å	Cell parameters from 1252 reflections
c = 11.6529 (12) Å	θ = 2.5–27.5°
α = 99.735 (2)°	µ = 0.31 mm⁻¹
β = 98.242 (1)°	T = 298 K
γ = 92.248 (1)°	Triclinic, colourless
V = 591.97 (10) Å³	0.49 × 0.40 × 0.24 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2068 independent reflections
Radiation source: fine-focus sealed tube	1517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
T_min = 0.862, T_max = 0.929	k = −11→9
3097 measured reflections	l = −13→13

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0463P)² + 0.1542P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2068 reflections	Δρ_max = 0.20 e Å⁻³
147 parameters	Δρ_min = −0.21 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: 0.294 (14)

Crystal data top

C₁₂H₁₅ClO₃	γ = 92.248 (1)°
M_r = 242.69	V = 591.97 (10) Å³
Triclinic, P1	Z = 2
a = 5.2750 (4) Å	Mo Kα radiation
b = 9.8941 (10) Å	µ = 0.31 mm⁻¹
c = 11.6529 (12) Å	T = 298 K
α = 99.735 (2)°	0.49 × 0.40 × 0.24 mm
β = 98.242 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2068 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1517 reflections with I > 2σ(I)
T_min = 0.862, T_max = 0.929	R_int = 0.019
3097 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 0.20 e Å⁻³
2068 reflections	Δρ_min = −0.21 e Å⁻³
147 parameters

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	0.69127 (14)	0.39709 (8)	0.91715 (5)	0.0668 (3)
O1	−0.6516 (3)	−0.02779 (17)	0.10226 (14)	0.0545 (5)
O2	−0.2483 (3)	−0.06891 (15)	0.23591 (14)	0.0513 (5)
H2	−0.3821	−0.0896	0.1897	0.077*
O3	0.2113 (3)	0.32392 (15)	0.48072 (12)	0.0444 (4)
C1	−0.7899 (4)	0.1907 (3)	0.0771 (2)	0.0508 (6)
H1A	−0.9234	0.1367	0.0217	0.076*
H1B	−0.6955	0.2480	0.0370	0.076*
H1C	−0.8647	0.2473	0.1371	0.076*
C2	−0.6130 (4)	0.0977 (2)	0.13236 (17)	0.0385 (5)
C3	−0.3944 (4)	0.1550 (2)	0.22183 (17)	0.0338 (5)
C4	−0.2210 (4)	0.0684 (2)	0.27035 (17)	0.0349 (5)
C5	−0.0135 (4)	0.1209 (2)	0.35608 (18)	0.0379 (5)
H5	0.1012	0.0623	0.3866	0.045*
C6	0.0206 (4)	0.2611 (2)	0.39548 (17)	0.0357 (5)
C7	−0.1489 (4)	0.3496 (2)	0.34910 (18)	0.0407 (5)
H7	−0.1254	0.4439	0.3761	0.049*
C8	−0.3499 (4)	0.2967 (2)	0.26358 (18)	0.0390 (5)
H8	−0.4606	0.3566	0.2321	0.047*
C9	0.3983 (4)	0.2437 (2)	0.53460 (18)	0.0400 (5)
H9A	0.5055	0.2040	0.4783	0.048*
H9B	0.3150	0.1700	0.5636	0.048*
C10	0.5562 (4)	0.3405 (2)	0.63445 (19)	0.0433 (6)
H10A	0.4454	0.3780	0.6899	0.052*
H10B	0.6285	0.4163	0.6039	0.052*
C11	0.7719 (4)	0.2729 (2)	0.69890 (18)	0.0440 (6)
H11A	0.7030	0.1880	0.7170	0.053*
H11B	0.8976	0.2495	0.6469	0.053*
C12	0.9052 (4)	0.3603 (3)	0.8113 (2)	0.0517 (6)
H12A	0.9737	0.4459	0.7941	0.062*
H12B	1.0479	0.3128	0.8443	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0704 (5)	0.0785 (5)	0.0487 (4)	0.0060 (4)	0.0128 (3)	0.0000 (3)
O1	0.0550 (10)	0.0450 (10)	0.0549 (10)	−0.0085 (8)	−0.0092 (8)	0.0018 (8)
O2	0.0548 (10)	0.0345 (9)	0.0583 (10)	0.0009 (7)	−0.0059 (8)	0.0026 (7)
O3	0.0404 (9)	0.0406 (9)	0.0452 (9)	0.0034 (7)	−0.0114 (7)	0.0026 (7)
C1	0.0449 (14)	0.0580 (16)	0.0450 (13)	−0.0012 (11)	−0.0079 (11)	0.0097 (11)
C2	0.0355 (12)	0.0454 (14)	0.0339 (11)	−0.0028 (10)	0.0052 (9)	0.0068 (10)
C3	0.0321 (11)	0.0373 (12)	0.0317 (10)	0.0002 (9)	0.0054 (9)	0.0048 (9)
C4	0.0366 (12)	0.0329 (12)	0.0346 (11)	0.0012 (9)	0.0068 (9)	0.0031 (9)
C5	0.0367 (12)	0.0390 (13)	0.0382 (11)	0.0078 (9)	0.0028 (9)	0.0086 (9)
C6	0.0321 (11)	0.0416 (13)	0.0326 (10)	0.0005 (9)	0.0027 (9)	0.0062 (9)
C7	0.0428 (13)	0.0336 (12)	0.0426 (12)	0.0037 (9)	−0.0018 (10)	0.0042 (10)
C8	0.0379 (12)	0.0394 (13)	0.0384 (11)	0.0065 (9)	−0.0019 (9)	0.0087 (9)
C9	0.0368 (12)	0.0439 (13)	0.0390 (12)	0.0068 (10)	0.0033 (9)	0.0074 (10)
C10	0.0390 (12)	0.0444 (13)	0.0434 (12)	0.0035 (10)	−0.0021 (10)	0.0057 (10)
C11	0.0360 (12)	0.0546 (15)	0.0408 (12)	0.0086 (10)	0.0033 (10)	0.0079 (11)
C12	0.0396 (13)	0.0678 (17)	0.0460 (13)	0.0051 (11)	−0.0020 (11)	0.0123 (12)

Geometric parameters (Å, º) top

Cl1—C12	1.791 (2)	C6—C7	1.393 (3)
O1—C2	1.232 (2)	C7—C8	1.367 (3)
O2—C4	1.346 (2)	C7—H7	0.9300
O2—H2	0.8200	C8—H8	0.9300
O3—C6	1.357 (2)	C9—C10	1.499 (3)
O3—C9	1.431 (2)	C9—H9A	0.9700
C1—C2	1.493 (3)	C9—H9B	0.9700
C1—H1A	0.9600	C10—C11	1.513 (3)
C1—H1B	0.9600	C10—H10A	0.9700
C1—H1C	0.9600	C10—H10B	0.9700
C2—C3	1.464 (3)	C11—C12	1.504 (3)
C3—C4	1.402 (3)	C11—H11A	0.9700
C3—C8	1.403 (3)	C11—H11B	0.9700
C4—C5	1.390 (3)	C12—H12A	0.9700
C5—C6	1.382 (3)	C12—H12B	0.9700
C5—H5	0.9300

C4—O2—H2	109.5	C7—C8—H8	119.0
C6—O3—C9	119.86 (16)	C3—C8—H8	119.0
C2—C1—H1A	109.5	O3—C9—C10	106.13 (17)
C2—C1—H1B	109.5	O3—C9—H9A	110.5
H1A—C1—H1B	109.5	C10—C9—H9A	110.5
C2—C1—H1C	109.5	O3—C9—H9B	110.5
H1A—C1—H1C	109.5	C10—C9—H9B	110.5
H1B—C1—H1C	109.5	H9A—C9—H9B	108.7
O1—C2—C3	120.04 (19)	C9—C10—C11	113.12 (18)
O1—C2—C1	119.69 (19)	C9—C10—H10A	109.0
C3—C2—C1	120.26 (19)	C11—C10—H10A	109.0
C4—C3—C8	117.24 (18)	C9—C10—H10B	109.0
C4—C3—C2	120.54 (18)	C11—C10—H10B	109.0
C8—C3—C2	122.21 (18)	H10A—C10—H10B	107.8
O2—C4—C5	117.17 (18)	C12—C11—C10	114.25 (19)
O2—C4—C3	121.47 (18)	C12—C11—H11A	108.7
C5—C4—C3	121.36 (19)	C10—C11—H11A	108.7
C6—C5—C4	119.31 (19)	C12—C11—H11B	108.7
C6—C5—H5	120.3	C10—C11—H11B	108.7
C4—C5—H5	120.3	H11A—C11—H11B	107.6
O3—C6—C5	124.69 (18)	C11—C12—Cl1	111.58 (16)
O3—C6—C7	114.72 (18)	C11—C12—H12A	109.3
C5—C6—C7	120.59 (19)	Cl1—C12—H12A	109.3
C8—C7—C6	119.5 (2)	C11—C12—H12B	109.3
C8—C7—H7	120.3	Cl1—C12—H12B	109.3
C6—C7—H7	120.3	H12A—C12—H12B	108.0
C7—C8—C3	122.01 (19)

O1—C2—C3—C4	2.8 (3)	C4—C5—C6—O3	178.18 (18)
C1—C2—C3—C4	−177.19 (19)	C4—C5—C6—C7	−0.8 (3)
O1—C2—C3—C8	−176.56 (19)	O3—C6—C7—C8	−179.25 (18)
C1—C2—C3—C8	3.5 (3)	C5—C6—C7—C8	−0.2 (3)
C8—C3—C4—O2	179.90 (18)	C6—C7—C8—C3	1.1 (3)
C2—C3—C4—O2	0.6 (3)	C4—C3—C8—C7	−0.9 (3)
C8—C3—C4—C5	−0.1 (3)	C2—C3—C8—C7	178.46 (19)
C2—C3—C4—C5	−179.47 (18)	C6—O3—C9—C10	−172.47 (17)
O2—C4—C5—C6	−179.10 (18)	O3—C9—C10—C11	−177.85 (18)
C3—C4—C5—C6	0.9 (3)	C9—C10—C11—C12	−170.21 (19)
C9—O3—C6—C5	1.4 (3)	C10—C11—C12—Cl1	63.0 (2)
C9—O3—C6—C7	−179.63 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.82	2.539 (2)	146

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅ClO₃
M_r	242.69
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.2750 (4), 9.8941 (10), 11.6529 (12)
α, β, γ (°)	99.735 (2), 98.242 (1), 92.248 (1)
V (Å³)	591.97 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.49 × 0.40 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.862, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	3097, 2068, 1517
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.06
No. of reflections	2068
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 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	1.82	2.539 (2)	146

Acknowledgements

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

References

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Dermer, O. C. (1934). Chem. Rev. 14, 385–430. CrossRef CAS Google Scholar
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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