Dichlorido[methyl 2-(quinolin-8-yl-oxy-κ(2)N,O)acetate-κO]mercury(II).

In the neutral title complex, [HgCl(2)(C(12)H(11)NO(3))], the Hg(II) ion is penta-coordinated by two Cl atoms, one N atom and two weakly coordinating O atoms from the methyl 2-(quinolin-8-yl-oxy)acetate ligand. The coordination around the Hg(II) ion may be described as highly distorted trigonal-bipyramidal. Centrosymmetric dimers are formed by an additional weak Hg⋯Cl inter-action, leading to a distorted octa-hedral coordination geometry around the Hg(II) ion.

Related literature

For the use of quinolin-8-yl­oxy acetic acid and its derivatives as ligands in transition metal complexes, see: Cheng et al. (2007 ▶); Song et al. (2004 ▶); Wang et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

[HgCl2(C12H11NO3)]

M = 488.71

Triclinic,

a = 7.2644 (4) Å

b = 9.7607 (2) Å

c = 10.8411 (6) Å

α = 71.317 (7)°

β = 75.453 (7)°

γ = 69.816 (8)°

V = 674.87 (5) Å3

Z = 2

Mo Kα radiation

μ = 11.80 mm−1

T = 223 K

0.50 × 0.25 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.067, T max = 0.385

5090 measured reflections

2432 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.142

S = 1.07

2432 reflections

174 parameters

H-atom parameters constrained

Δρmax = 3.58 e Å−3

Δρmin = −2.39 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812026591/im2385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026591/im2385Isup2.hkl

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

[HgCl2(C12H11NO3)]	Z = 2
Mr = 488.71	F(000) = 456
Triclinic, P1	Dx = 2.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.2644 (4) Å	Cell parameters from 3438 reflections
b = 9.7607 (2) Å	θ = 3.0–27.5°
c = 10.8411 (6) Å	µ = 11.80 mm−1
α = 71.317 (7)°	T = 223 K
β = 75.453 (7)°	Prism, yellow
γ = 69.816 (8)°	0.50 × 0.25 × 0.10 mm
V = 674.87 (5) Å3

Rigaku Saturn diffractometer	2432 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→9
Tmin = 0.067, Tmax = 0.385	l = −13→10
5090 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.114P)2] where P = (Fo2 + 2Fc2)/3
2432 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 3.58 e Å−3
0 restraints	Δρmin = −2.39 e Å−3

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.

	x	y	z	Uiso*/Ueq
Hg1	0.48080 (4)	0.17195 (3)	0.82524 (2)	0.0283 (2)
Cl1	0.7584 (4)	0.0079 (3)	0.9214 (2)	0.0343 (5)
Cl2	0.2251 (4)	0.2330 (3)	0.7032 (2)	0.0328 (5)
O1	0.5887 (9)	0.4276 (6)	0.6794 (5)	0.0267 (12)
O2	0.9795 (10)	0.3004 (7)	0.4386 (6)	0.0293 (13)
O3	0.7782 (11)	0.1803 (7)	0.5930 (6)	0.0350 (15)
N1	0.3624 (11)	0.3914 (8)	0.9197 (6)	0.0229 (14)
C1	0.2572 (13)	0.3719 (9)	1.0411 (8)	0.0250 (17)
H1	0.2485	0.2744	1.0883	0.030*
C2	0.1591 (14)	0.4918 (11)	1.1008 (8)	0.0291 (19)
H2	0.0929	0.4727	1.1882	0.035*
C3	0.1596 (13)	0.6348 (10)	1.0327 (8)	0.0280 (18)
H3	0.0892	0.7160	1.0707	0.034*
C4	0.2680 (12)	0.6597 (9)	0.9034 (7)	0.0229 (16)
C5	0.2793 (15)	0.8066 (10)	0.8262 (9)	0.032 (2)
H5	0.2102	0.8915	0.8595	0.038*
C6	0.3906 (15)	0.8224 (9)	0.7043 (9)	0.0306 (19)
H6	0.3995	0.9189	0.6541	0.037*
C7	0.4920 (14)	0.6985 (10)	0.6522 (8)	0.0288 (19)
H7	0.5649	0.7133	0.5665	0.035*
C8	0.4873 (13)	0.5564 (9)	0.7230 (8)	0.0232 (16)
C9	0.3727 (12)	0.5317 (9)	0.8506 (7)	0.0226 (16)
C10	0.7341 (16)	0.4428 (10)	0.5679 (8)	0.030 (2)
H10A	0.8339	0.4787	0.5842	0.037*
H10B	0.6737	0.5164	0.4927	0.037*
C11	0.8301 (13)	0.2914 (9)	0.5380 (7)	0.0221 (16)
C12	1.0873 (14)	0.1595 (10)	0.3990 (9)	0.0313 (19)
H12A	1.1489	0.0841	0.4717	0.047*
H12B	1.1890	0.1780	0.3236	0.047*
H12C	0.9953	0.1234	0.3756	0.047*

	U11	U22	U33	U12	U13	U23
Hg1	0.0304 (3)	0.0247 (3)	0.0247 (3)	−0.00519 (19)	−0.00101 (17)	−0.00514 (17)
Cl1	0.0304 (12)	0.0320 (12)	0.0350 (11)	−0.0028 (10)	−0.0050 (9)	−0.0083 (9)
Cl2	0.0360 (13)	0.0344 (11)	0.0255 (10)	−0.0096 (10)	−0.0038 (9)	−0.0057 (8)
O1	0.027 (3)	0.025 (3)	0.022 (3)	−0.011 (3)	0.017 (2)	−0.009 (2)
O2	0.030 (3)	0.025 (3)	0.028 (3)	−0.006 (3)	0.010 (3)	−0.012 (2)
O3	0.041 (4)	0.025 (3)	0.034 (3)	−0.013 (3)	0.014 (3)	−0.012 (2)
N1	0.027 (4)	0.023 (3)	0.019 (3)	−0.008 (3)	0.002 (3)	−0.009 (3)
C1	0.024 (4)	0.030 (4)	0.021 (4)	−0.007 (4)	0.000 (3)	−0.009 (3)
C2	0.029 (5)	0.039 (5)	0.019 (4)	−0.012 (4)	0.005 (4)	−0.012 (3)
C3	0.018 (4)	0.038 (5)	0.030 (4)	−0.005 (4)	0.003 (3)	−0.019 (4)
C4	0.020 (4)	0.024 (4)	0.022 (4)	−0.001 (3)	0.002 (3)	−0.011 (3)
C5	0.041 (6)	0.025 (4)	0.034 (4)	−0.012 (4)	0.000 (4)	−0.014 (4)
C6	0.034 (5)	0.017 (4)	0.034 (5)	−0.004 (4)	−0.003 (4)	−0.003 (3)
C7	0.035 (5)	0.028 (4)	0.022 (4)	−0.009 (4)	−0.002 (4)	−0.005 (3)
C8	0.021 (4)	0.020 (4)	0.024 (4)	−0.003 (3)	0.003 (3)	−0.009 (3)
C9	0.018 (4)	0.030 (4)	0.020 (3)	−0.006 (3)	−0.001 (3)	−0.009 (3)
C10	0.041 (6)	0.032 (5)	0.018 (4)	−0.015 (4)	0.010 (4)	−0.012 (3)
C11	0.023 (4)	0.024 (4)	0.019 (4)	−0.009 (3)	0.005 (3)	−0.008 (3)
C12	0.023 (5)	0.029 (5)	0.035 (5)	−0.002 (4)	0.011 (4)	−0.018 (4)

Hg1—Cl1	2.340 (2)	C3—C4	1.416 (12)
Hg1—Cl2	2.350 (2)	C3—H3	0.9400
Hg1—N1	2.463 (6)	C4—C9	1.432 (11)
Hg1—O1	2.746 (6)	C4—C5	1.428 (12)
Hg1—O3	2.876 (6)	C5—C6	1.357 (13)
Hg1—Cl1i	3.204 (2)	C5—H5	0.9400
O1—C8	1.383 (10)	C6—C7	1.392 (13)
O1—C10	1.396 (10)	C6—H6	0.9400
O2—C11	1.329 (10)	C7—C8	1.361 (12)
O2—C12	1.468 (10)	C7—H7	0.9400
O3—C11	1.195 (10)	C8—C9	1.418 (11)
N1—C1	1.337 (11)	C10—C11	1.502 (12)
N1—C9	1.352 (11)	C10—H10A	0.9800
C1—C2	1.405 (12)	C10—H10B	0.9800
C1—H1	0.9400	C12—H12A	0.9700
C2—C3	1.355 (14)	C12—H12B	0.9700
C2—H2	0.9400	C12—H12C	0.9700
Cl1—Hg1—Cl2	153.41 (8)	C3—C4—C5	122.3 (7)
Cl1—Hg1—N1	106.61 (17)	C9—C4—C5	119.5 (7)
Cl2—Hg1—N1	99.30 (17)	C6—C5—C4	119.5 (8)
Cl1—Hg1—O1	105.43 (15)	C6—C5—H5	120.3
Cl2—Hg1—O1	91.75 (15)	C4—C5—H5	120.3
N1—Hg1—O1	62.08 (19)	C5—C6—C7	121.3 (8)
Cl1—Hg1—O3	80.81 (15)	C5—C6—H6	119.4
Cl2—Hg1—O3	92.53 (16)	C7—C6—H6	119.4
N1—Hg1—O3	117.7 (2)	C8—C7—C6	121.2 (8)
O1—Hg1—O3	56.55 (16)	C8—C7—H7	119.4
Cl1—Hg1—Cl1i	83.50 (8)	C6—C7—H7	119.4
Cl2—Hg1—Cl1i	90.92 (7)	C7—C8—O1	124.5 (7)
N1—Hg1—Cl1i	89.63 (16)	C7—C8—C9	120.5 (7)
O1—Hg1—Cl1i	151.64 (12)	O1—C8—C9	115.1 (7)
O3—Hg1—Cl1i	151.45 (13)	N1—C9—C8	120.7 (7)
C8—O1—C10	116.4 (6)	N1—C9—C4	121.2 (7)
C8—O1—Hg1	115.6 (4)	C8—C9—C4	118.0 (7)
C10—O1—Hg1	128.0 (5)	O1—C10—C11	108.5 (7)
C11—O2—C12	115.3 (7)	O1—C10—H10A	110.0
C11—O3—Hg1	121.0 (5)	C11—C10—H10A	110.0
C1—N1—C9	119.1 (7)	O1—C10—H10B	110.0
C1—N1—Hg1	116.1 (5)	C11—C10—H10B	110.0
C9—N1—Hg1	124.1 (5)	H10A—C10—H10B	108.4
N1—C1—C2	122.4 (8)	O3—C11—O2	124.9 (8)
N1—C1—H1	118.8	O3—C11—C10	125.5 (8)
C2—C1—H1	118.8	O2—C11—C10	109.6 (7)
C3—C2—C1	120.2 (8)	O2—C12—H12A	109.5
C3—C2—H2	119.9	O2—C12—H12B	109.5
C1—C2—H2	119.9	H12A—C12—H12B	109.5
C2—C3—C4	118.8 (8)	O2—C12—H12C	109.5
C2—C3—H3	120.6	H12A—C12—H12C	109.5
C4—C3—H3	120.6	H12B—C12—H12C	109.5
C3—C4—C9	118.2 (7)
Cl1—Hg1—O1—C8	−113.6 (5)	C3—C4—C5—C6	178.0 (9)
Cl2—Hg1—O1—C8	86.9 (5)	C9—C4—C5—C6	−0.6 (13)
N1—Hg1—O1—C8	−12.7 (5)	C4—C5—C6—C7	0.9 (15)
O3—Hg1—O1—C8	178.8 (6)	C5—C6—C7—C8	−1.8 (15)
Cl1i—Hg1—O1—C8	−8.3 (7)	C6—C7—C8—O1	−178.0 (8)
Cl1—Hg1—O1—C10	65.7 (7)	C6—C7—C8—C9	2.2 (14)
Cl2—Hg1—O1—C10	−93.8 (7)	C10—O1—C8—C7	13.2 (13)
N1—Hg1—O1—C10	166.6 (8)	Hg1—O1—C8—C7	−167.4 (7)
O3—Hg1—O1—C10	−1.9 (7)	C10—O1—C8—C9	−167.0 (8)
Cl1i—Hg1—O1—C10	171.0 (6)	Hg1—O1—C8—C9	12.4 (9)
Cl1—Hg1—O3—C11	−110.2 (7)	C1—N1—C9—C8	178.2 (8)
Cl2—Hg1—O3—C11	95.7 (7)	Hg1—N1—C9—C8	−11.9 (11)
N1—Hg1—O3—C11	−6.1 (8)	C1—N1—C9—C4	−2.1 (11)
O1—Hg1—O3—C11	5.3 (6)	Hg1—N1—C9—C4	167.8 (6)
Cl1i—Hg1—O3—C11	−167.7 (5)	C7—C8—C9—N1	177.9 (8)
Cl1—Hg1—N1—C1	−78.3 (6)	O1—C8—C9—N1	−1.9 (11)
Cl2—Hg1—N1—C1	95.7 (6)	C7—C8—C9—C4	−1.8 (12)
O1—Hg1—N1—C1	−177.3 (7)	O1—C8—C9—C4	178.4 (7)
O3—Hg1—N1—C1	−166.5 (5)	C3—C4—C9—N1	2.7 (12)
Cl1i—Hg1—N1—C1	4.8 (6)	C5—C4—C9—N1	−178.7 (8)
Cl1—Hg1—N1—C9	111.5 (6)	C3—C4—C9—C8	−177.6 (8)
Cl2—Hg1—N1—C9	−74.5 (6)	C5—C4—C9—C8	1.0 (11)
O1—Hg1—N1—C9	12.5 (6)	C8—O1—C10—C11	178.6 (7)
O3—Hg1—N1—C9	23.4 (7)	Hg1—O1—C10—C11	−0.7 (11)
Cl1i—Hg1—N1—C9	−165.4 (6)	Hg1—O3—C11—O2	173.0 (6)
C9—N1—C1—C2	−1.0 (12)	Hg1—O3—C11—C10	−8.8 (12)
Hg1—N1—C1—C2	−171.7 (7)	C12—O2—C11—O3	−1.6 (12)
N1—C1—C2—C3	3.6 (14)	C12—O2—C11—C10	179.9 (7)
C1—C2—C3—C4	−2.9 (13)	O1—C10—C11—O3	6.4 (13)
C2—C3—C4—C9	−0.1 (12)	O1—C10—C11—O2	−175.1 (7)
C2—C3—C4—C5	−178.7 (9)

Table 1

Selected bond lengths (Å)

Hg1—Cl1	2.340 (2)
Hg1—Cl2	2.350 (2)
Hg1—N1	2.463 (6)
Hg1—O1	2.746 (6)
Hg1—O3	2.876 (6)
Hg1—Cl1i	3.204 (2)

Symmetry code: (i) .