Chlorido(2-formyl-6-hydroxy-phenyl-κC)mercury(II).

In the planar [r.m.s. deviation 0.0265 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 a benzene ring and a Cl atom. The benzene C atom and the aldehyde O atom chelate the Hg(II) atom by assuming the Hg⋯O separation of 2.817 (9) Å as a weak intra-molecular coordination bonding distance. The resulting five-membered metallacycle is nearly coplanar with the benzene ring dihedral angle 2.9 (1)°]. Inter-molecular O-H⋯O hydrogen bonds are present in the crystal structure, resulting in a one-dimensional supra-molecular architecture parallel to [201].

Related literature

For historical background and for properties of cyclo­metallated compounds, see: Dupont et al. (2005 ▶); Xu et al. (2009 ▶). For the properties of cyclo­mercurated compounds, see: Wu et al. (2001 ▶); Ryabov et al. (2003 ▶). For related structure, see: King et al. (2002 ▶); Zhou et al. (2005 ▶); Hao et al. (2007 ▶).

Experimental

Crystal data

[Hg(C7H5O2)Cl]

M = 357.15

Monoclinic,

a = 4.7200 (19) Å

b = 17.702 (7) Å

c = 10.506 (4) Å

β = 98.839 (5)°

V = 867.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 18.00 mm−1

T = 296 K

0.08 × 0.01 × 0.01 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.327, T max = 0.841

5002 measured reflections

1595 independent reflections

1130 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 1.01

1595 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −2.32 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902145X/si2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902145X/si2180Isup2.hkl

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

[Hg(C7H5O2)Cl]	F(000) = 640
Mr = 357.15	Dx = 2.735 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.7200 (19) Å	Cell parameters from 1175 reflections
b = 17.702 (7) Å	θ = 2.3–22.3°
c = 10.506 (4) Å	µ = 18.00 mm−1
β = 98.839 (5)°	T = 296 K
V = 867.4 (6) Å3	Block, colourless
Z = 4	0.08 × 0.01 × 0.01 mm

Bruker SMART APEX CCD area-detector diffractometer	1595 independent reflections
Radiation source: fine-focus sealed tube	1130 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.327, Tmax = 0.841	k = −21→21
5002 measured reflections	l = −12→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0564P)2 + 3.2348P] where P = (Fo2 + 2Fc2)/3
1595 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −2.32 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.26063 (12)	0.66539 (3)	0.30597 (6)	0.0470 (2)
O1	−0.160 (2)	0.6917 (5)	0.5036 (10)	0.050 (2)
H1	−0.2948	0.6960	0.5439	0.074*
O2	0.468 (2)	0.7878 (5)	0.1758 (9)	0.052 (2)
Cl1	0.4684 (11)	0.5580 (2)	0.2416 (5)	0.0833 (14)
C1	0.345 (3)	0.8403 (7)	0.2208 (14)	0.043 (3)
H1A	0.3802	0.8888	0.1928	0.052*
C2	0.151 (3)	0.8330 (7)	0.3132 (13)	0.042 (3)
C3	0.039 (3)	0.8998 (7)	0.3574 (14)	0.051 (4)
H3	0.0837	0.9460	0.3235	0.061*
C4	−0.137 (3)	0.8974 (7)	0.4509 (13)	0.048 (4)
H4	−0.2123	0.9420	0.4788	0.058*
C5	−0.204 (3)	0.8276 (7)	0.5043 (13)	0.044 (3)
H5	−0.3193	0.8257	0.5683	0.053*
C6	−0.092 (3)	0.7611 (7)	0.4591 (12)	0.042 (3)
C7	0.087 (2)	0.7635 (7)	0.3644 (11)	0.032 (3)

	U11	U22	U33	U12	U13	U23
Hg1	0.0477 (4)	0.0392 (3)	0.0583 (4)	0.0027 (3)	0.0213 (3)	−0.0048 (3)
O1	0.047 (6)	0.048 (5)	0.060 (6)	−0.006 (4)	0.027 (5)	0.003 (5)
O2	0.047 (6)	0.058 (6)	0.056 (6)	−0.003 (5)	0.028 (5)	−0.011 (5)
Cl1	0.098 (4)	0.044 (2)	0.117 (4)	0.016 (2)	0.045 (3)	−0.010 (2)
C1	0.033 (7)	0.043 (7)	0.054 (8)	−0.002 (6)	0.007 (6)	0.005 (7)
C2	0.029 (6)	0.053 (8)	0.043 (7)	−0.008 (6)	0.007 (6)	0.000 (6)
C3	0.058 (9)	0.034 (7)	0.070 (10)	0.012 (6)	0.038 (8)	0.012 (7)
C4	0.056 (9)	0.035 (7)	0.056 (9)	0.006 (6)	0.012 (7)	−0.010 (6)
C5	0.040 (8)	0.053 (8)	0.044 (8)	0.005 (7)	0.020 (6)	−0.007 (7)
C6	0.027 (7)	0.054 (8)	0.045 (8)	−0.012 (6)	0.007 (6)	0.000 (6)
C7	0.023 (6)	0.043 (7)	0.026 (6)	−0.004 (5)	−0.008 (5)	0.001 (5)

Hg1—C7	2.052 (12)	C2—C3	1.403 (17)
Hg1—Cl1	2.288 (4)	C3—C4	1.382 (17)
O1—C6	1.370 (14)	C3—H3	0.9300
O1—H1	0.8200	C4—C5	1.412 (18)
O2—C1	1.229 (14)	C4—H4	0.9300
C1—C2	1.440 (18)	C5—C6	1.402 (17)
C1—H1A	0.9300	C5—H5	0.9300
C2—C7	1.394 (16)	C6—C7	1.403 (16)
C7—Hg1—Cl1	178.1 (3)	C3—C4—H4	119.9
C6—O1—H1	109.5	C5—C4—H4	119.9
O2—C1—C2	125.4 (12)	C6—C5—C4	118.9 (11)
O2—C1—H1A	117.3	C6—C5—H5	120.6
C2—C1—H1A	117.3	C4—C5—H5	120.6
C7—C2—C1	122.4 (12)	O1—C6—C7	117.8 (11)
C7—C2—C3	120.1 (12)	O1—C6—C5	121.2 (11)
C1—C2—C3	117.3 (11)	C7—C6—C5	121.0 (12)
C4—C3—C2	120.6 (12)	C2—C7—C6	119.2 (11)
C4—C3—H3	119.7	C2—C7—Hg1	120.8 (9)
C2—C3—H3	119.7	C6—C7—Hg1	119.9 (9)
C3—C4—C5	120.2 (11)
O2—C1—C2—C7	2(2)	C3—C2—C7—C6	0.8 (19)
O2—C1—C2—C3	177.6 (14)	C1—C2—C7—Hg1	−1.9 (18)
C7—C2—C3—C4	−1(2)	C3—C2—C7—Hg1	−177.8 (10)
C1—C2—C3—C4	−176.7 (14)	O1—C6—C7—C2	177.3 (12)
C2—C3—C4—C5	1(2)	C5—C6—C7—C2	−1.1 (19)
C3—C4—C5—C6	−1(2)	O1—C6—C7—Hg1	−4.2 (16)
C4—C5—C6—O1	−177.0 (12)	C5—C6—C7—Hg1	177.4 (10)
C4—C5—C6—C7	1(2)	Cl1—Hg1—C7—C2	46 (10)
C1—C2—C7—C6	176.6 (12)	Cl1—Hg1—C7—C6	−132 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.93	2.730 (12)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.93	2.730 (12)	165

Symmetry code: (i) .