Diiodido[methyl 2-(quinolin-8-yl-oxy)-acetate-κN]mercury(II).

In the title mononuclear complex, [HgI(2)(C(12)H(11)NO(3))], the Hg(II) ion has a distorted trigonal-planar coordination sphere defined by two I(-) anions and the N atom of a methyl 2-(quinolin-8-yl-oxy)acetate ligand. In the crystal, face-to-face π-π stacking inter-actions, with a centroid-centroid distance of 3.563 (9) Å, are observed.

Related literature

For derivatives of quinoline, see: Cheng et al. (2007 ▶); Ghedini et al. (2002 ▶); Inomata et al. (1999 ▶); Jotterand et al. (2001 ▶). For transition metal coordination compounds of 8-quinolinyloxy­acetic acid, see: Cheng et al. (2007 ▶); Song et al. (2004 ▶); Wang et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

[HgI2(C12H11NO3)]

M = 671.61

Triclinic,

a = 7.5889 (5) Å

b = 10.3670 (7) Å

c = 11.4241 (11) Å

α = 72.203 (18)°

β = 74.40 (2)°

γ = 68.644 (19)°

V = 784.33 (15) Å3

Z = 2

Mo Kα radiation

μ = 13.75 mm−1

T = 223 K

0.30 × 0.15 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.095, T max = 0.191

6692 measured reflections

2912 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.104

S = 1.08

2912 reflections

127 parameters

H-atom parameters constrained

Δρmax = 1.74 e Å−3

Δρmin = −2.02 e Å−3

Data collection: CrystalClear (Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 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/S1600536812031017/rz2782sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031017/rz2782Isup2.hkl

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

[HgI2(C12H11NO3)]	Z = 2
Mr = 671.61	F(000) = 600
Triclinic, P1	Dx = 2.844 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.5889 (5) Å	Cell parameters from 3945 reflections
b = 10.3670 (7) Å	θ = 3.0–27.5°
c = 11.4241 (11) Å	µ = 13.75 mm−1
α = 72.203 (18)°	T = 223 K
β = 74.40 (2)°	Block, colourless
γ = 68.644 (19)°	0.30 × 0.15 × 0.12 mm
V = 784.33 (15) Å3

Rigaku Saturn diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→12
Tmin = 0.095, Tmax = 0.191	l = −13→11
6692 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0218P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2912 reflections	Δρmax = 1.74 e Å−3
127 parameters	Δρmin = −2.02 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0122 (6)

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	0.51208 (7)	0.82132 (6)	0.69012 (5)	0.0363 (2)
I1	0.20950 (11)	0.98926 (10)	0.59179 (9)	0.0367 (3)
I2	0.79754 (12)	0.77753 (11)	0.80042 (9)	0.0407 (3)
O1	0.4074 (12)	0.5817 (10)	0.8269 (8)	0.036 (2)
O2	0.2395 (13)	0.8117 (11)	0.9230 (9)	0.044 (3)
O3	0.0431 (12)	0.7026 (11)	1.0766 (9)	0.044 (3)
N1	0.6241 (13)	0.6124 (11)	0.5978 (11)	0.032 (3)
C1	0.7266 (17)	0.6246 (15)	0.4837 (13)	0.0351 (11)
H1	0.7388	0.7148	0.4404	0.042*
C2	0.8204 (17)	0.5104 (14)	0.4210 (13)	0.0351 (11)
H2	0.8916	0.5259	0.3396	0.042*
C3	0.8046 (17)	0.3814 (15)	0.4808 (13)	0.0351 (11)
H3	0.8640	0.3053	0.4409	0.042*
C4	0.6940 (18)	0.3573 (15)	0.6095 (13)	0.0351 (11)
C5	0.6720 (17)	0.2266 (15)	0.6712 (13)	0.0351 (11)
H5	0.7304	0.1489	0.6334	0.042*
C6	0.5686 (17)	0.2116 (15)	0.7835 (13)	0.0351 (11)
H6	0.5565	0.1212	0.8261	0.042*
C7	0.4726 (17)	0.3280 (14)	0.8446 (13)	0.0351 (11)
H7	0.3990	0.3159	0.9255	0.042*
C8	0.4950 (18)	0.4584 (15)	0.7775 (13)	0.0351 (11)
C9	0.6036 (18)	0.4816 (15)	0.6632 (13)	0.0351 (11)
C10	0.2660 (17)	0.5716 (16)	0.9448 (14)	0.041 (4)
H10A	0.1636	0.5416	0.9346	0.050*
H10B	0.3295	0.5001	1.0119	0.050*
C11	0.1829 (19)	0.7104 (17)	0.9780 (15)	0.040 (4)
C12	−0.052 (2)	0.8306 (17)	1.1242 (14)	0.056 (5)
H12A	0.0373	0.8482	1.1598	0.083*
H12B	−0.1621	0.8181	1.1881	0.083*
H12C	−0.0946	0.9109	1.0565	0.083*

	U11	U22	U33	U12	U13	U23
Hg1	0.0374 (3)	0.0355 (4)	0.0358 (4)	−0.0110 (2)	−0.0080 (2)	−0.0067 (3)
I1	0.0336 (5)	0.0352 (6)	0.0399 (6)	−0.0105 (4)	−0.0073 (4)	−0.0065 (5)
I2	0.0408 (5)	0.0497 (7)	0.0322 (6)	−0.0198 (4)	−0.0088 (4)	−0.0011 (5)
O1	0.045 (5)	0.034 (6)	0.026 (6)	−0.013 (4)	0.013 (4)	−0.018 (5)
O2	0.052 (6)	0.045 (7)	0.036 (7)	−0.019 (5)	0.012 (5)	−0.019 (6)
O3	0.046 (5)	0.055 (7)	0.028 (6)	−0.022 (5)	0.017 (4)	−0.017 (6)
N1	0.030 (6)	0.018 (6)	0.050 (8)	−0.005 (5)	−0.011 (5)	−0.010 (6)
C1	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C2	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C3	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C4	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C5	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C6	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C7	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C8	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C9	0.038 (2)	0.032 (3)	0.032 (3)	−0.011 (2)	−0.0028 (19)	−0.005 (2)
C10	0.033 (7)	0.053 (10)	0.033 (9)	−0.024 (7)	−0.010 (6)	0.014 (8)
C11	0.041 (8)	0.038 (9)	0.040 (10)	−0.018 (7)	−0.016 (7)	0.007 (8)
C12	0.068 (10)	0.064 (12)	0.029 (10)	−0.024 (9)	0.029 (8)	−0.030 (9)

Hg1—N1	2.470 (9)	C4—C5	1.371 (19)
Hg1—I1	2.6163 (12)	C4—C9	1.456 (17)
Hg1—I2	2.6246 (11)	C5—C6	1.308 (18)
O1—C8	1.419 (14)	C5—H5	0.9400
O1—C10	1.482 (15)	C6—C7	1.441 (16)
O2—C11	1.209 (17)	C6—H6	0.9400
O3—C11	1.328 (17)	C7—C8	1.381 (19)
O3—C12	1.452 (15)	C7—H7	0.9400
N1—C1	1.321 (17)	C8—C9	1.348 (19)
N1—C9	1.377 (17)	C10—C11	1.469 (19)
C1—C2	1.432 (16)	C10—H10A	0.9800
C1—H1	0.9400	C10—H10B	0.9800
C2—C3	1.336 (19)	C12—H12A	0.9700
C2—H2	0.9400	C12—H12B	0.9700
C3—C4	1.481 (19)	C12—H12C	0.9700
C3—H3	0.9400
N1—Hg1—I1	104.4 (2)	C7—C6—H6	118.7
N1—Hg1—I2	102.2 (2)	C8—C7—C6	116.1 (13)
I1—Hg1—I2	151.47 (4)	C8—C7—H7	121.9
C8—O1—C10	117.4 (10)	C6—C7—H7	121.9
C11—O3—C12	116.1 (11)	C9—C8—C7	124.7 (12)
C1—N1—C9	118.9 (10)	C9—C8—O1	113.5 (12)
C1—N1—Hg1	117.2 (9)	C7—C8—O1	121.7 (12)
C9—N1—Hg1	123.5 (9)	C8—C9—N1	123.9 (12)
N1—C1—C2	124.8 (13)	C8—C9—C4	114.8 (13)
N1—C1—H1	117.6	N1—C9—C4	121.2 (12)
C2—C1—H1	117.6	C11—C10—O1	109.9 (12)
C3—C2—C1	118.5 (13)	C11—C10—H10A	109.7
C3—C2—H2	120.7	O1—C10—H10A	109.7
C1—C2—H2	120.7	C11—C10—H10B	109.7
C2—C3—C4	120.5 (12)	O1—C10—H10B	109.7
C2—C3—H3	119.8	H10A—C10—H10B	108.2
C4—C3—H3	119.8	O2—C11—O3	127.6 (13)
C5—C4—C9	122.5 (13)	O2—C11—C10	123.5 (13)
C5—C4—C3	121.4 (11)	O3—C11—C10	108.8 (13)
C9—C4—C3	116.1 (12)	O3—C12—H12A	109.5
C6—C5—C4	119.1 (12)	O3—C12—H12B	109.5
C6—C5—H5	120.4	H12A—C12—H12B	109.5
C4—C5—H5	120.4	O3—C12—H12C	109.5
C5—C6—C7	122.6 (14)	H12A—C12—H12C	109.5
C5—C6—H6	118.7	H12B—C12—H12C	109.5
I1—Hg1—N1—C1	80.1 (9)	C7—C8—C9—N1	−180.0 (12)
I2—Hg1—N1—C1	−89.5 (9)	O1—C8—C9—N1	−1.9 (19)
I1—Hg1—N1—C9	−107.3 (9)	C7—C8—C9—C4	2 (2)
I2—Hg1—N1—C9	83.1 (9)	O1—C8—C9—C4	−179.4 (10)
C9—N1—C1—C2	−0.1 (19)	C1—N1—C9—C8	−176.7 (13)
Hg1—N1—C1—C2	172.9 (9)	Hg1—N1—C9—C8	10.8 (18)
N1—C1—C2—C3	0 (2)	C1—N1—C9—C4	0.7 (18)
C1—C2—C3—C4	−0.7 (19)	Hg1—N1—C9—C4	−171.9 (8)
C2—C3—C4—C5	178.3 (13)	C5—C4—C9—C8	−0.7 (19)
C2—C3—C4—C9	1.2 (18)	C3—C4—C9—C8	176.4 (12)
C9—C4—C5—C6	−1 (2)	C5—C4—C9—N1	−178.3 (12)
C3—C4—C5—C6	−178.1 (12)	C3—C4—C9—N1	−1.2 (18)
C4—C5—C6—C7	1 (2)	C8—O1—C10—C11	−177.0 (10)
C5—C6—C7—C8	0.2 (19)	C12—O3—C11—O2	0 (2)
C6—C7—C8—C9	−2 (2)	C12—O3—C11—C10	178.5 (11)
C6—C7—C8—O1	179.8 (10)	O1—C10—C11—O2	−7.3 (19)
C10—O1—C8—C9	172.5 (11)	O1—C10—C11—O3	173.7 (10)
C10—O1—C8—C7	−9.4 (17)