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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2424
https://doi.org/10.1107/S1600536812030838

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

Hoong-Kun Fun,a*‡ Ching Kheng Quah,a§ Divya N. Shetty,b B. Narayanab and B. K. Sarojinic

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
*Correspondence e-mail: hkfun@usm.my

(Received 4 July 2012; accepted 6 July 2012; online 10 July 2012)

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[Erian, A. W., Sherif, S. M. & Gaber, H. M. (2003). Molecules, 8, 793-865.]); Qing & Zhang (2009[Qing, W.-X. & Zhang, W. (2009). Acta Cryst. E65, o2837.]); Fun et al. (2012[Fun, H.-K., Quah, C. K., Priya, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o818.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C8H7ClO2

  • Mr = 170.59

  • Monoclinic, P 21 /c

  • 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.803, Tmax = 0.925

  • 16799 measured reflections

  • 4352 independent reflections

  • 4037 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.073

  • S = 1.03

  • 4352 reflections

  • 207 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1B—H2O1⋯O2Ai 0.812 (16) 1.973 (16) 2.7742 (11) 168.7 (16)
O1A—H1O1⋯O2Bii 0.840 (16) 1.891 (16) 2.7229 (10) 170.4 (16)
C4A—H4AA⋯O2Bii 0.95 2.47 3.1780 (12) 131
C8A—H8AA⋯O1Aiii 0.99 2.58 3.5228 (12) 160
C2B—H2BA⋯O2Ai 0.95 2.44 3.1603 (12) 133
C4B—H4BA⋯O1Aiv 0.95 2.58 3.5126 (12) 166
Symmetry codes: (i) x-1, y, z; (ii) x, y, z-1; (iii) -x+1, -y+2, -z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030838/sj5254sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030838/sj5254Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030838/sj5254Isup3.cml

checkCIF report


Comment top

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].

Related literature top

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 top

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).

Refinement top

O-bound hydrogen atoms were located in a difference Fourier map and refined freely with O–H = 0.814 (17) - 0.840 (17) Å. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.95 or 0.99 Å and Uiso(H) = 1.2 Ueq(C).

Structure description top

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].

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Fig. 1. The asymmetric unit of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.
2-Chloro-1-(4-hydroxyphenyl)ethanone top
Crystal data top
C8H7ClO2F(000) = 704
Mr = 170.59Dx = 1.520 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9970 reflections
a = 7.4931 (5) Åθ = 2.7–30.1°
b = 14.7345 (10) ŵ = 0.45 mm−1
c = 13.5681 (10) ÅT = 100 K
β = 95.560 (1)°Block, colourless
V = 1490.97 (18) Å30.51 × 0.23 × 0.18 mm
Z = 8
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		4352 independent reflections
Radiation source: fine-focus sealed tube4037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 30.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −9→10
Tmin = 0.803, Tmax = 0.925k = −20→20
16799 measured reflectionsl = −19→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.037P)2 + 0.5857P]
where P = (Fo2 + 2Fc2)/3
4352 reflections(Δ/σ)max = 0.003
207 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C8H7ClO2V = 1490.97 (18) Å3
Mr = 170.59Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.4931 (5) ŵ = 0.45 mm−1
b = 14.7345 (10) ÅT = 100 K
c = 13.5681 (10) Å0.51 × 0.23 × 0.18 mm
β = 95.560 (1)°
Data collection top
Bruker SMART APEXII DUO CCD area-detector
diffractometer		4352 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		4037 reflections with I > 2σ(I)
Tmin = 0.803, Tmax = 0.925Rint = 0.019
16799 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.46 e Å−3
4352 reflectionsΔρmin = −0.23 e Å−3
207 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
Cl1A1.09654 (3)1.232822 (15)0.175736 (18)0.02002 (7)
O1A0.51043 (9)0.80027 (5)−0.05945 (5)0.01637 (13)
O2A1.01029 (10)1.04907 (5)0.22919 (5)0.01973 (14)
C1A0.79616 (12)0.91436 (6)0.13312 (7)0.01573 (17)
H1AA0.84610.90290.19900.019*
C2A0.69221 (12)0.84846 (6)0.08224 (7)0.01577 (17)
H2AA0.67160.79200.11300.019*
C3A0.61778 (12)0.86551 (6)−0.01468 (7)0.01370 (16)
C4A0.65279 (12)0.94739 (6)−0.06163 (7)0.01386 (16)
H4AA0.60600.9580−0.12820.017*
C5A0.75661 (12)1.01286 (6)−0.00971 (7)0.01353 (16)
H5AA0.77941.0687−0.04110.016*
C6A0.82845 (11)0.99793 (6)0.08835 (7)0.01357 (16)
C7A0.93813 (12)1.06615 (6)0.14663 (7)0.01399 (16)
C8A0.95428 (12)1.15941 (6)0.10015 (7)0.01518 (16)
H8AA0.83361.18700.08870.018*
H8AB1.00221.15260.03510.018*
Cl1B0.32249 (4)0.674926 (16)0.744284 (18)0.02232 (7)
O1B0.21395 (11)1.12541 (5)0.38976 (6)0.02120 (15)
O2B0.39854 (10)0.86748 (5)0.75803 (5)0.02074 (15)
C1B0.20436 (12)0.90119 (6)0.50470 (7)0.01514 (16)
H1BA0.16320.84130.48970.018*
C2B0.17605 (12)0.96844 (6)0.43372 (7)0.01547 (17)
H2BA0.11560.95500.37060.019*
C3B0.23734 (12)1.05637 (6)0.45581 (7)0.01522 (17)
C4B0.32607 (13)1.07671 (6)0.54895 (7)0.01661 (17)
H4BA0.36741.13660.56360.020*
C5B0.35289 (12)1.00894 (6)0.61929 (7)0.01579 (17)
H5BA0.41261.02270.68250.019*
C6B0.29280 (12)0.91996 (6)0.59837 (7)0.01388 (16)
C7B0.32576 (12)0.85017 (6)0.67533 (7)0.01461 (16)
C8B0.26334 (13)0.75424 (6)0.64795 (7)0.01729 (17)
H8BA0.31730.73500.58760.021*
H8BB0.13140.75430.63270.021*
H2O10.162 (2)1.1077 (11)0.3380 (12)0.034 (4)*
H1O10.480 (2)0.8153 (11)−0.1184 (12)0.032 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.02376 (12)0.01545 (11)0.02045 (12)−0.00383 (8)0.00009 (8)−0.00221 (8)
O1A0.0183 (3)0.0151 (3)0.0150 (3)−0.0022 (2)−0.0020 (2)−0.0001 (2)
O2A0.0253 (3)0.0182 (3)0.0145 (3)−0.0026 (3)−0.0043 (3)0.0019 (3)
C1A0.0188 (4)0.0149 (4)0.0130 (4)0.0001 (3)−0.0006 (3)0.0023 (3)
C2A0.0190 (4)0.0141 (4)0.0140 (4)−0.0002 (3)0.0003 (3)0.0025 (3)
C3A0.0130 (3)0.0136 (4)0.0143 (4)0.0010 (3)0.0008 (3)−0.0012 (3)
C4A0.0146 (4)0.0147 (4)0.0120 (4)0.0017 (3)−0.0001 (3)0.0009 (3)
C5A0.0148 (4)0.0126 (4)0.0131 (4)0.0011 (3)0.0010 (3)0.0013 (3)
C6A0.0150 (4)0.0129 (4)0.0127 (4)0.0007 (3)0.0008 (3)0.0005 (3)
C7A0.0152 (4)0.0139 (4)0.0129 (4)0.0010 (3)0.0014 (3)0.0002 (3)
C8A0.0167 (4)0.0136 (4)0.0149 (4)−0.0005 (3)−0.0005 (3)0.0007 (3)
Cl1B0.03273 (13)0.01561 (11)0.01846 (12)0.00168 (8)0.00162 (9)0.00428 (8)
O1B0.0316 (4)0.0143 (3)0.0161 (3)−0.0032 (3)−0.0060 (3)0.0030 (3)
O2B0.0284 (4)0.0187 (3)0.0139 (3)−0.0009 (3)−0.0047 (3)0.0002 (3)
C1B0.0186 (4)0.0123 (4)0.0141 (4)−0.0009 (3)−0.0008 (3)−0.0017 (3)
C2B0.0189 (4)0.0141 (4)0.0127 (4)0.0001 (3)−0.0021 (3)−0.0012 (3)
C3B0.0180 (4)0.0131 (4)0.0142 (4)0.0002 (3)0.0001 (3)0.0006 (3)
C4B0.0203 (4)0.0131 (4)0.0159 (4)−0.0025 (3)−0.0009 (3)−0.0018 (3)
C5B0.0185 (4)0.0150 (4)0.0132 (4)−0.0014 (3)−0.0017 (3)−0.0020 (3)
C6B0.0160 (4)0.0129 (4)0.0125 (4)0.0001 (3)0.0002 (3)−0.0004 (3)
C7B0.0164 (4)0.0140 (4)0.0133 (4)0.0003 (3)0.0010 (3)−0.0007 (3)
C8B0.0240 (4)0.0135 (4)0.0139 (4)−0.0004 (3)−0.0003 (3)0.0013 (3)
Geometric parameters (Å, º) top
Cl1A—C8A1.7738 (10)Cl1B—C8B1.7772 (10)
O1A—C3A1.3585 (11)O1B—C3B1.3559 (11)
O1A—H1O10.840 (17)O1B—H2O10.814 (17)
O2A—C7A1.2219 (11)O2B—C7B1.2260 (12)
C1A—C2A1.3863 (13)C1B—C2B1.3838 (13)
C1A—C6A1.4043 (12)C1B—C6B1.4027 (13)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.4005 (13)C2B—C3B1.3973 (13)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.4009 (12)C3B—C4B1.4021 (13)
C4A—C5A1.3879 (12)C4B—C5B1.3824 (13)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.4034 (12)C5B—C6B1.4062 (12)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.4783 (12)C6B—C7B1.4693 (12)
C7A—C8A1.5217 (13)C7B—C8B1.5235 (13)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C3A—O1A—H1O1109.5 (11)C3B—O1B—H2O1110.5 (12)
C2A—C1A—C6A120.72 (9)C2B—C1B—C6B121.09 (8)
C2A—C1A—H1AA119.6C2B—C1B—H1BA119.5
C6A—C1A—H1AA119.6C6B—C1B—H1BA119.5
C1A—C2A—C3A119.69 (8)C1B—C2B—C3B119.32 (8)
C1A—C2A—H2AA120.2C1B—C2B—H2BA120.3
C3A—C2A—H2AA120.2C3B—C2B—H2BA120.3
O1A—C3A—C2A117.23 (8)O1B—C3B—C2B122.35 (8)
O1A—C3A—C4A122.34 (8)O1B—C3B—C4B117.07 (8)
C2A—C3A—C4A120.43 (8)C2B—C3B—C4B120.58 (8)
C5A—C4A—C3A119.23 (8)C5B—C4B—C3B119.50 (8)
C5A—C4A—H4AA120.4C5B—C4B—H4BA120.3
C3A—C4A—H4AA120.4C3B—C4B—H4BA120.3
C4A—C5A—C6A121.12 (8)C4B—C5B—C6B120.79 (9)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.6
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.6
C5A—C6A—C1A118.77 (8)C1B—C6B—C5B118.72 (8)
C5A—C6A—C7A122.87 (8)C1B—C6B—C7B122.54 (8)
C1A—C6A—C7A118.36 (8)C5B—C6B—C7B118.73 (8)
O2A—C7A—C6A121.60 (8)O2B—C7B—C6B122.28 (8)
O2A—C7A—C8A121.34 (8)O2B—C7B—C8B121.00 (8)
C6A—C7A—C8A117.05 (8)C6B—C7B—C8B116.72 (8)
C7A—C8A—Cl1A112.24 (7)C7B—C8B—Cl1B112.46 (7)
C7A—C8A—H8AA109.2C7B—C8B—H8BA109.1
Cl1A—C8A—H8AA109.2Cl1B—C8B—H8BA109.1
C7A—C8A—H8AB109.2C7B—C8B—H8BB109.1
Cl1A—C8A—H8AB109.2Cl1B—C8B—H8BB109.1
H8AA—C8A—H8AB107.9H8BA—C8B—H8BB107.8
C6A—C1A—C2A—C3A−0.33 (14)C6B—C1B—C2B—C3B0.25 (14)
C1A—C2A—C3A—O1A−177.08 (8)C1B—C2B—C3B—O1B−179.94 (9)
C1A—C2A—C3A—C4A2.21 (13)C1B—C2B—C3B—C4B−0.25 (14)
O1A—C3A—C4A—C5A176.85 (8)O1B—C3B—C4B—C5B179.73 (9)
C2A—C3A—C4A—C5A−2.41 (13)C2B—C3B—C4B—C5B0.03 (14)
C3A—C4A—C5A—C6A0.73 (13)C3B—C4B—C5B—C6B0.21 (14)
C4A—C5A—C6A—C1A1.11 (13)C2B—C1B—C6B—C5B−0.02 (14)
C4A—C5A—C6A—C7A−179.37 (8)C2B—C1B—C6B—C7B−179.75 (9)
C2A—C1A—C6A—C5A−1.32 (13)C4B—C5B—C6B—C1B−0.21 (14)
C2A—C1A—C6A—C7A179.14 (8)C4B—C5B—C6B—C7B179.53 (9)
C5A—C6A—C7A—O2A−174.44 (9)C1B—C6B—C7B—O2B−177.86 (9)
C1A—C6A—C7A—O2A5.08 (13)C5B—C6B—C7B—O2B2.41 (14)
C5A—C6A—C7A—C8A6.77 (12)C1B—C6B—C7B—C8B1.60 (13)
C1A—C6A—C7A—C8A−173.71 (8)C5B—C6B—C7B—C8B−178.13 (8)
O2A—C7A—C8A—Cl1A3.57 (11)O2B—C7B—C8B—Cl1B−4.04 (12)
C6A—C7A—C8A—Cl1A−177.63 (6)C6B—C7B—C8B—Cl1B176.49 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H2O1···O2Ai0.812 (16)1.973 (16)2.7742 (11)168.7 (16)
O1A—H1O1···O2Bii0.840 (16)1.891 (16)2.7229 (10)170.4 (16)
C4A—H4AA···O2Bii0.952.473.1780 (12)131
C8A—H8AA···O1Aiii0.992.583.5228 (12)160
C2B—H2BA···O2Ai0.952.443.1603 (12)133
C4B—H4BA···O1Aiv0.952.583.5126 (12)166
Symmetry codes: (i) x−1, y, z; (ii) x, y, z−1; (iii) −x+1, −y+2, −z; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC8H7ClO2
Mr170.59
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.4931 (5), 14.7345 (10), 13.5681 (10)
β (°) 95.560 (1)
V (Å3)1490.97 (18)
Z8
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.51 × 0.23 × 0.18
Data collection
DiffractometerBruker SMART APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.803, 0.925
No. of measured, independent and
observed [I > 2σ(I)] reflections		16799, 4352, 4037
Rint0.019
(sin θ/λ)max (Å−1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.073, 1.03
No. of reflections4352
No. of parameters207
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.46, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H2O1···O2Ai0.812 (16)1.973 (16)2.7742 (11)168.7 (16)
O1A—H1O1···O2Bii0.840 (16)1.891 (16)2.7229 (10)170.4 (16)
C4A—H4AA···O2Bii0.95002.47003.1780 (12)131.00
C8A—H8AA···O1Aiii0.99002.58003.5228 (12)160.00
C2B—H2BA···O2Ai0.95002.44003.1603 (12)133.00
C4B—H4BA···O1Aiv0.95002.58003.5126 (12)166.00
Symmetry codes: (i) x−1, y, z; (ii) x, y, z−1; (iii) −x+1, −y+2, −z; (iv) −x+1, y+1/2, −z+1/2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

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.

References

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 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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 First citationFun, H.-K., Quah, C. K., Priya, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o818.  CSD CrossRef IUCr Journals Google Scholar
 First citationQing, W.-X. & Zhang, W. (2009). Acta Cryst. E65, o2837.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page o2424
https://doi.org/10.1107/S1600536812030838
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