2-Chloro-1-(4-hy­droxy­phen­yl)ethanone

Hoong-Kun Fun; Ching Kheng Quah; Divya N Shetty; B Narayana; B K Sarojini

doi:10.1107/S1600536812030838

. 2012 Jul 10;68(Pt 8):o2424. doi: 10.1107/S1600536812030838

2-Chloro-1-(4-hydroxyphenyl)ethanone

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Divya N Shetty ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3414342 PMID: 22904875

Abstract

The asymmetric unit of the title compound, C₈H₇ClO₂, consists of two independent molecules, with comparable geometries. Both molecules are approximately planar (r.m.s. deviations = 0.040 and 0.064 Å for the 11 non-H atoms). In the crystal, molecules are linked via intermolecular O—H⋯O and C—H⋯O hydrogen bonds into chains two molecules thick along (-101).

Related literature

For general background to and related structures of the title compound, see: Erian et al. (2003 ▶); Qing & Zhang (2009 ▶); Fun et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₈H₇ClO₂
M _r = 170.59
Monoclinic,
a = 7.4931 (5) Å
b = 14.7345 (10) Å
c = 13.5681 (10) Å
β = 95.560 (1)°
V = 1490.97 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 100 K
0.51 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.803, T _max = 0.925
16799 measured reflections
4352 independent reflections
4037 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.073
S = 1.03
4352 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030838/sj5254sup1.cif

e-68-o2424-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030838/sj5254Isup2.hkl

e-68-o2424-Isup2.hkl^{(213.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030838/sj5254Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1B—H2O1⋯O2A ⁱ	0.812 (16)	1.973 (16)	2.7742 (11)	168.7 (16)
O1A—H1O1⋯O2B ⁱⁱ	0.840 (16)	1.891 (16)	2.7229 (10)	170.4 (16)
C4A—H4AA⋯O2B ⁱⁱ	0.95	2.47	3.1780 (12)	131
C8A—H8AA⋯O1A ⁱⁱⁱ	0.99	2.58	3.5228 (12)	160
C2B—H2BA⋯O2A ⁱ	0.95	2.44	3.1603 (12)	133
C4B—H4BA⋯O1A ^iv	0.95	2.58	3.5126 (12)	166

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors would like to thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. BN thanks the UGC SAP for financial assistance for the purchase of chemicals. DNS thanks Mangalore University for chemicals and facilities for synthesizing the title compound.

supplementary crystallographic information

Comment

In view of the importance of α-haloketones in heterocyclic synthesis and their reactivity towards oxygen nucleophiles (Erian et al., 2003), the crystal structure of title compond (I) is reported. The crystal structure of the bromo analogue of the title compound has also been reported (Qing & Zhang, 2009).

The asymmetric unit (Fig. 1) of the title compound consists of two independent molecules (A and B), with comparable geometries. Both molecules (A and B) are approximately planar (r.m.s. deviation = 0.040 and 0.064 Å, respectively, for the eleven non-H atoms). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with a related structure (Fun et al., 2012).

In the crystal structure, Fig. 2, molecules are linked via intermolecular O1B–H1O2···O2A, O1A–H1O1···O2B, C4A–H4AA···O2B, C8A–H8AA···O1A, C2B–H2BA···O2A and C4B–H4BA···O1A hydrogen bonds (Table 1) into two-molecular-thick chains along the [-101].

Experimental

The title compound, 2-chloro-1-(4-hydroxyphenyl)ethanone, was purchased from Sigma-Aldrich and recrystallized from methanol by the slow evaporation method (m.p. 422 K).