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

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

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.103
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

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Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          6
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT158_ALERT_4_C The Input Unitcell is NOT Standard/Reduced .....          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               1946
           Count of symmetry unique reflns         1181
           Completeness (_total/calc)            164.78%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       765
           Fraction of Friedel pairs measured     0.648
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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   3 ALERT type 4 Improvement, methodology, query or suggestion
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S1. Comment

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

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

S2. Experimental

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,%.

S3. Refinement

All H atoms were positioned geometrically, with O—H= 0.82 Å, C—H=0.93- 0.97 Å, and refined as riding, with U_iso(H)=1.2–1.5U_eq(C, O).

Computing details

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

Fig. 1. The molecular structure of (I) with atomic numbering and 30% probability displacement ellipsoids.

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.49 × 0.44 × 0.43 mm
F(000) = 480

Data collection

Bruker Smart APEX CCD area-detector diffractometer	1946 independent reflections
Radiation source: fine-focus sealed tube	1556 reflections with I > 2σ(I)
Graphite monochromator	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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.0435P] where P = (Fo^2 + 2Fc^2)/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	Absolute structure parameter: −0.16 (10)

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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