3-Chloro-meth-yl-2-hy-droxy-benzaldehyde.

In the title compound, C(8)H(7)ClO(2), the hydroxyl and aldehyde groups are co-planar with the benzene ring [maximum deviation 0.018 (3) Å], and the Cl-C-C plane is almost perpendicular to the benzene ring [dihedral angle 83.7 (2)°]. An intra-molecular O-H⋯O hydrogen bond occurs between the hydroxyl and aldehyde groups.

Related literature

For related structures, see: Zondervan et al. (1997 ▶); Tang et al. (2010 ▶). For the synthesis, see: Song & Liu (2004 ▶).

Experimental

Crystal data

C8H7ClO2

M = 170.59

Orthorhombic,

a = 4.483 (6) Å

b = 12.521 (18) Å

c = 13.71 (2) Å

V = 769.6 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.30 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.88, T max = 0.92

3730 measured reflections

1369 independent reflections

1075 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.133

S = 0.98

1369 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 6571 Friedel pairs

Flack parameter: −0.06 (13)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038421/xu5608sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038421/xu5608Isup2.hkl

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

C8H7ClO2	F(000) = 352
Mr = 170.59	Dx = 1.472 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1369 reflections
a = 4.483 (6) Å	θ = 2.2–25.0°
b = 12.521 (18) Å	µ = 0.44 mm−1
c = 13.71 (2) Å	T = 293 K
V = 769.6 (19) Å3	Block, colorless
Z = 4	0.30 × 0.23 × 0.18 mm

Bruker APEXII CCD diffractometer	1369 independent reflections
Radiation source: fine-focus sealed tube	1075 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scan	θmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→5
Tmin = 0.88, Tmax = 0.92	k = −15→14
3730 measured reflections	l = −16→16

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
1369 reflections	Δρmax = 0.31 e Å−3
101 parameters	Δρmin = −0.32 e Å−3
0 restraints	Absolute structure: Flack (1983), 6571 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (13)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.5383 (2)	0.21212 (5)	0.21927 (5)	0.0606 (3)
O1	0.3758 (7)	−0.05428 (14)	0.16474 (16)	0.0558 (7)
H1	0.2636	−0.1057	0.1598	0.084*
O2	0.0222 (7)	−0.18989 (15)	0.07502 (19)	0.0640 (7)
C11	0.6216 (8)	0.07288 (19)	0.0685 (2)	0.0440 (7)
C12	0.4289 (7)	−0.01314 (17)	0.0756 (2)	0.0384 (7)
C13	0.2937 (8)	−0.05626 (17)	−0.0076 (2)	0.0403 (7)
C14	0.3593 (9)	−0.0101 (2)	−0.0985 (2)	0.0509 (9)
H14A	0.2719	−0.0378	−0.1546	0.061*
C15	0.5488 (10)	0.0745 (2)	−0.1057 (2)	0.0560 (9)
H15A	0.5907	0.1043	−0.1663	0.067*
C16	0.6779 (9)	0.1157 (2)	−0.0228 (3)	0.0507 (8)
H16A	0.8062	0.1738	−0.0282	0.061*
C17	0.7744 (9)	0.1173 (3)	0.1567 (3)	0.0572 (9)
H17A	0.9581	0.1522	0.1371	0.069*
H17B	0.8252	0.0594	0.2007	0.069*
C18	0.0905 (9)	−0.14473 (19)	−0.0012 (2)	0.0504 (9)
H18A	0.0050	−0.1695	−0.0587	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.0771 (7)	0.0537 (4)	0.0510 (5)	−0.0025 (4)	−0.0076 (4)	−0.0126 (3)
O1	0.078 (2)	0.0496 (10)	0.0400 (12)	−0.0038 (11)	−0.0019 (12)	0.0056 (7)
O2	0.074 (2)	0.0533 (9)	0.0649 (15)	−0.0091 (11)	0.0058 (15)	0.0042 (9)
C11	0.045 (2)	0.0425 (11)	0.0443 (16)	0.0089 (12)	−0.0040 (13)	−0.0039 (10)
C12	0.0424 (18)	0.0371 (9)	0.0358 (13)	0.0089 (11)	0.0027 (14)	0.0003 (9)
C13	0.042 (2)	0.0386 (10)	0.0398 (16)	0.0085 (12)	−0.0002 (13)	−0.0032 (9)
C14	0.067 (3)	0.0507 (12)	0.0353 (15)	0.0082 (14)	−0.0039 (16)	−0.0031 (10)
C15	0.067 (3)	0.0583 (14)	0.0427 (17)	0.0024 (16)	0.0070 (17)	0.0048 (11)
C16	0.050 (2)	0.0474 (12)	0.055 (2)	−0.0035 (14)	0.0055 (17)	0.0036 (12)
C17	0.054 (2)	0.0597 (14)	0.058 (2)	0.0024 (15)	−0.0145 (17)	−0.0069 (14)
C18	0.053 (2)	0.0412 (11)	0.057 (2)	0.0004 (12)	0.0011 (17)	−0.0076 (11)

Cl1—C17	1.808 (4)	C13—C18	1.437 (4)
O1—C12	1.348 (4)	C14—C15	1.362 (5)
O1—H1	0.8200	C14—H14A	0.9300
O2—C18	1.227 (4)	C15—C16	1.376 (5)
C11—C12	1.384 (4)	C15—H15A	0.9300
C11—C16	1.386 (5)	C16—H16A	0.9300
C11—C17	1.496 (5)	C17—H17A	0.9700
C12—C13	1.400 (4)	C17—H17B	0.9700
C13—C14	1.404 (4)	C18—H18A	0.9300
C12—O1—H1	109.5	C14—C15—H15A	120.2
C12—C11—C16	118.6 (3)	C16—C15—H15A	120.2
C12—C11—C17	121.2 (3)	C15—C16—C11	121.7 (3)
C16—C11—C17	120.2 (3)	C15—C16—H16A	119.2
O1—C12—C11	118.1 (3)	C11—C16—H16A	119.2
O1—C12—C13	121.0 (3)	C11—C17—Cl1	111.1 (3)
C11—C12—C13	120.9 (3)	C11—C17—H17A	109.4
C12—C13—C14	118.2 (3)	Cl1—C17—H17A	109.4
C12—C13—C18	121.5 (3)	C11—C17—H17B	109.4
C14—C13—C18	120.3 (3)	Cl1—C17—H17B	109.4
C15—C14—C13	121.0 (3)	H17A—C17—H17B	108.0
C15—C14—H14A	119.5	O2—C18—C13	124.5 (3)
C13—C14—H14A	119.5	O2—C18—H18A	117.8
C14—C15—C16	119.6 (3)	C13—C18—H18A	117.8
C16—C11—C12—O1	180.0 (3)	C18—C13—C14—C15	179.3 (3)
C17—C11—C12—O1	1.8 (4)	C13—C14—C15—C16	−0.1 (5)
C16—C11—C12—C13	0.1 (4)	C14—C15—C16—C11	0.4 (5)
C17—C11—C12—C13	−178.1 (3)	C12—C11—C16—C15	−0.4 (5)
O1—C12—C13—C14	−179.7 (3)	C17—C11—C16—C15	177.8 (3)
C11—C12—C13—C14	0.2 (4)	C12—C11—C17—Cl1	−84.7 (3)
O1—C12—C13—C18	0.9 (4)	C16—C11—C17—Cl1	97.2 (4)
C11—C12—C13—C18	−179.3 (3)	C12—C13—C18—O2	−0.9 (5)
C12—C13—C14—C15	−0.2 (5)	C14—C13—C18—O2	179.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.91	2.628 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.91	2.628 (5)	146