3,5-Dichloro-2-hydroxy-benzaldehyde.

The title compound, C(7)H(4)Cl(2)O(2), exhibits a layer crystal structure; mol-ecules within each layer are linked by weak C-H⋯O inter-molecular hydrogen bonds. There is also an intramolecular O-H⋯O hydrogen bond.

Related literature

For a related compound, see: Fan et al. (2008 ▶).

Experimental

Crystal data

C7H4Cl2O2

M = 191.00

Monoclinic,

a = 8.3359 (16) Å

b = 13.884 (3) Å

c = 7.2341 (14) Å

β = 114.519 (2)°

V = 761.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 291 (2) K

0.14 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.897, T max = 0.925

4063 measured reflections

1487 independent reflections

1181 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 0.99

1487 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808013901/at2566sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013901/at2566Isup2.hkl

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

C7H4Cl2O2	F000 = 384
Mr = 191.00	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1691 reflections
a = 8.3359 (16) Å	θ = 2.7–26.8º
b = 13.884 (3) Å	µ = 0.79 mm−1
c = 7.2341 (14) Å	T = 291 (2) K
β = 114.519 (2)º	Block, yellow
V = 761.7 (3) Å3	0.14 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1487 independent reflections
Radiation source: fine-focus sealed tube	1181 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.055
T = 291(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.898, Tmax = 0.925	k = −16→16
4063 measured reflections	l = −7→8

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
1487 reflections	Δρmax = 0.27 e Å−3
101 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
C1	0.4748 (2)	0.35190 (14)	0.2605 (3)	0.0419 (5)
C2	0.5509 (2)	0.26110 (14)	0.2721 (3)	0.0383 (4)
C3	0.7213 (2)	0.25643 (14)	0.2822 (3)	0.0379 (4)
C4	0.8119 (2)	0.33830 (13)	0.2774 (3)	0.0422 (5)
H4	0.9261	0.3341	0.2858	0.051*
C5	0.7313 (2)	0.42742 (15)	0.2599 (3)	0.0422 (5)
C6	0.5658 (3)	0.43474 (15)	0.2547 (3)	0.0445 (5)
H6	0.5145	0.4949	0.2474	0.053*
C7	0.2987 (3)	0.35981 (17)	0.2606 (3)	0.0536 (6)
H7	0.2525	0.4210	0.2579	0.064*
Cl1	0.81885 (7)	0.14449 (4)	0.29976 (9)	0.0542 (2)
Cl2	0.84604 (7)	0.52989 (4)	0.24617 (10)	0.0612 (2)
O1	0.21042 (19)	0.29062 (13)	0.2640 (3)	0.0678 (5)
O2	0.46796 (18)	0.17843 (10)	0.2737 (2)	0.0519 (4)
H2	0.3694	0.1904	0.2670	0.078*

	U11	U22	U33	U12	U13	U23
C1	0.0364 (10)	0.0424 (12)	0.0505 (11)	0.0021 (8)	0.0216 (9)	0.0031 (9)
C2	0.0405 (10)	0.0354 (11)	0.0423 (10)	−0.0011 (8)	0.0206 (8)	0.0018 (8)
C3	0.0389 (10)	0.0360 (11)	0.0428 (10)	0.0048 (8)	0.0209 (8)	0.0000 (8)
C4	0.0357 (10)	0.0470 (14)	0.0483 (12)	0.0007 (8)	0.0218 (9)	0.0033 (9)
C5	0.0410 (11)	0.0383 (11)	0.0492 (11)	−0.0052 (8)	0.0209 (9)	0.0034 (9)
C6	0.0432 (11)	0.0367 (11)	0.0568 (12)	0.0050 (8)	0.0240 (10)	0.0045 (9)
C7	0.0427 (12)	0.0502 (14)	0.0746 (15)	0.0042 (10)	0.0310 (11)	0.0076 (11)
Cl1	0.0576 (4)	0.0406 (3)	0.0719 (4)	0.0126 (2)	0.0344 (3)	0.0019 (2)
Cl2	0.0515 (3)	0.0438 (4)	0.0914 (5)	−0.0092 (2)	0.0327 (3)	0.0102 (3)
O1	0.0463 (8)	0.0642 (12)	0.1052 (13)	−0.0007 (8)	0.0437 (8)	0.0073 (9)
O2	0.0475 (8)	0.0370 (8)	0.0773 (10)	−0.0056 (6)	0.0319 (8)	0.0020 (7)

C1—C6	1.388 (3)	C4—H4	0.9300
C1—C2	1.398 (3)	C5—C6	1.369 (3)
C1—C7	1.472 (3)	C5—Cl2	1.740 (2)
C2—O2	1.342 (2)	C6—H6	0.9300
C2—C3	1.393 (2)	C7—O1	1.217 (3)
C3—C4	1.373 (3)	C7—H7	0.9300
C3—Cl1	1.7340 (19)	O2—H2	0.8200
C4—C5	1.388 (3)
C6—C1—C2	120.59 (18)	C5—C4—H4	120.3
C6—C1—C7	119.71 (18)	C6—C5—C4	120.85 (18)
C2—C1—C7	119.68 (18)	C6—C5—Cl2	120.63 (16)
O2—C2—C3	118.51 (17)	C4—C5—Cl2	118.52 (14)
O2—C2—C1	123.29 (16)	C5—C6—C1	119.68 (18)
C3—C2—C1	118.20 (17)	C5—C6—H6	120.2
C4—C3—C2	121.30 (17)	C1—C6—H6	120.2
C4—C3—Cl1	119.86 (13)	O1—C7—C1	123.6 (2)
C2—C3—Cl1	118.84 (15)	O1—C7—H7	118.2
C3—C4—C5	119.34 (17)	C1—C7—H7	118.2
C3—C4—H4	120.3	C2—O2—H2	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.92	2.630 (2)	145
C4—H4···O1i	0.93	2.51	3.428 (3)	168
C6—H6···O2ii	0.93	2.56	3.394 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.92	2.630 (2)	145
C4—H4⋯O1i	0.93	2.51	3.428 (3)	168
C6—H6⋯O2ii	0.93	2.56	3.394 (3)	149

Symmetry codes: (i) ; (ii) .