Chlorido(5-formyl-2-hydroxy-phenyl-κC)mercury(II).

In the planar (r.m.s. deviation = 0.027 Å) title compound, [Hg(C(7)H(5)O(2))Cl], the Hg(II) atom shows a typical linear coordination by a C atom of the benzene ring and a Cl atom. Inter-molecular O-H⋯O hydrogen bonds are present in the crystal structure, resulting in chains propagating along the b axis. The crystal studied was a non-merohedral twin, with a twin ratio of 0.802 (2):0.198 (2).

Related literature

For general background to the use of cyclo­metallated compounds in synthesis, catalysis and materials, see: Gruter et al. (1995 ▶); Dupont et al. (2005 ▶). For related structures and the synthesis of related cyclo­mercurated compounds, see: Xu et al. (2009 ▶). For the preparation of cyclo­mercurated compounds, see: Ryabov et al. (2003 ▶); Wu et al. (2001 ▶).

Experimental

Crystal data

[Hg(C7H5O2)Cl]

M = 357.15

Monoclinic,

a = 4.1004 (10) Å

b = 14.842 (3) Å

c = 14.116 (3) Å

β = 106.657 (6)°

V = 823.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 18.97 mm−1

T = 295 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.116, T max = 0.151

4116 measured reflections

1424 independent reflections

1333 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.103

S = 1.09

1424 reflections

101 parameters

H-atom parameters constrained

Δρmax = 2.05 e Å−3

Δρmin = −1.73 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043529/hb5153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043529/hb5153Isup2.hkl

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

[Hg(C7H5O2)Cl]	F(000) = 640
Mr = 357.15	Dx = 2.882 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2640 reflections
a = 4.1004 (10) Å	θ = 2.7–29.5°
b = 14.842 (3) Å	µ = 18.97 mm−1
c = 14.116 (3) Å	T = 295 K
β = 106.657 (6)°	Block, colorless
V = 823.0 (3) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	1424 independent reflections
Radiation source: fine-focus sealed tube	1333 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.116, Tmax = 0.151	k = −12→17
4116 measured reflections	l = −16→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0429P)2 + 12.0653P] where P = (Fo2 + 2Fc2)/3
1424 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 2.05 e Å−3
0 restraints	Δρmin = −1.73 e Å−3

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
Hg1	0.32843 (16)	0.87897 (3)	0.53385 (4)	0.0345 (2)
Cl1	0.5374 (10)	0.9140 (2)	0.4016 (3)	0.0405 (8)
O1	0.093 (5)	1.0269 (8)	0.8767 (9)	0.076 (4)
O2	0.069 (4)	0.6993 (7)	0.5877 (8)	0.055 (3)
H2	0.0023	0.6493	0.5982	0.083*
C1	0.031 (5)	0.8833 (8)	0.8033 (11)	0.038 (3)
C2	0.131 (4)	0.9074 (9)	0.7223 (10)	0.033 (3)
H2A	0.1898	0.9671	0.7153	0.040*
C3	0.148 (4)	0.8460 (9)	0.6511 (9)	0.029 (3)
C4	0.052 (4)	0.7564 (10)	0.6613 (10)	0.036 (3)
C5	−0.063 (5)	0.7317 (9)	0.7410 (11)	0.042 (3)
H5	−0.1288	0.6724	0.7467	0.051*
C6	−0.081 (4)	0.7932 (10)	0.8110 (10)	0.039 (4)
H6	−0.1642	0.7766	0.8631	0.047*
C7	−0.007 (6)	0.9495 (12)	0.8760 (11)	0.059 (5)
H7	−0.1119	0.9319	0.9235	0.070*

	U11	U22	U33	U12	U13	U23
Hg1	0.0437 (3)	0.0258 (3)	0.0364 (3)	−0.0009 (2)	0.0153 (3)	0.0038 (2)
Cl1	0.050 (2)	0.0390 (18)	0.0357 (17)	−0.0049 (17)	0.0181 (16)	−0.0012 (15)
O1	0.133 (14)	0.035 (6)	0.067 (8)	−0.005 (8)	0.040 (9)	−0.009 (6)
O2	0.099 (11)	0.028 (5)	0.047 (6)	−0.014 (6)	0.033 (7)	−0.007 (5)
C1	0.050 (10)	0.022 (7)	0.043 (8)	0.011 (6)	0.015 (7)	0.002 (5)
C2	0.036 (8)	0.021 (6)	0.044 (8)	0.008 (6)	0.013 (6)	0.008 (6)
C3	0.032 (7)	0.021 (6)	0.030 (7)	0.002 (6)	0.003 (5)	0.007 (5)
C4	0.042 (8)	0.030 (7)	0.029 (7)	−0.003 (6)	0.002 (6)	0.003 (6)
C5	0.061 (10)	0.021 (6)	0.047 (8)	−0.005 (7)	0.020 (8)	0.008 (6)
C6	0.052 (9)	0.034 (8)	0.034 (7)	−0.005 (7)	0.014 (7)	0.016 (6)
C7	0.096 (15)	0.048 (10)	0.038 (9)	0.017 (10)	0.027 (10)	0.009 (7)

Hg1—C3	2.058 (13)	C2—C3	1.37 (2)
Hg1—Cl1	2.326 (4)	C2—H2A	0.9300
O1—C7	1.22 (2)	C3—C4	1.405 (19)
O2—C4	1.357 (17)	C4—C5	1.39 (2)
O2—H2	0.8193	C5—C6	1.36 (2)
C1—C2	1.37 (2)	C5—H5	0.9300
C1—C6	1.428 (19)	C6—H6	0.9300
C1—C7	1.46 (2)	C7—H7	0.9300
C3—Hg1—Cl1	179.1 (4)	O2—C4—C3	115.9 (13)
C4—O2—H2	109.5	C5—C4—C3	120.1 (13)
C2—C1—C6	119.2 (13)	C6—C5—C4	120.8 (13)
C2—C1—C7	121.9 (13)	C6—C5—H5	119.6
C6—C1—C7	118.4 (15)	C4—C5—H5	119.6
C1—C2—C3	121.8 (13)	C5—C6—C1	119.2 (13)
C1—C2—H2A	119.1	C5—C6—H6	120.4
C3—C2—H2A	119.1	C1—C6—H6	120.4
C2—C3—C4	118.7 (13)	O1—C7—C1	122.3 (17)
C2—C3—Hg1	122.4 (10)	O1—C7—H7	118.8
C4—C3—Hg1	118.8 (10)	C1—C7—H7	118.8
O2—C4—C5	123.9 (13)
C6—C1—C2—C3	−4(2)	O2—C4—C5—C6	−178.4 (16)
C7—C1—C2—C3	−176.1 (16)	C3—C4—C5—C6	−1(2)
C1—C2—C3—C4	1(2)	C4—C5—C6—C1	−2(3)
C1—C2—C3—Hg1	−175.8 (12)	C2—C1—C6—C5	4(2)
C2—C3—C4—O2	179.0 (14)	C7—C1—C6—C5	176.7 (16)
Hg1—C3—C4—O2	−3.9 (18)	C2—C1—C7—O1	−11 (3)
C2—C3—C4—C5	1(2)	C6—C1—C7—O1	177.2 (19)
Hg1—C3—C4—C5	178.5 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.91	2.727 (16)	172

Hg1—C3	2.058 (13)
Hg1—Cl1	2.326 (4)

C3—Hg1—Cl1

179.1 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.91	2.727 (16)	172

Symmetry code: (i) .