Dibromido[methyl 2-(quinolin-8-yl-oxy-κ(2)N,O)acetic acid-κO]mercury(II).

In the title complex, [HgBr(2)(C(12)H(11)NO(3))], the Hg(II) ion has a distorted core trigonal-planar geometry comprising two Br atoms and one quinoline N atom of the methyl 2-(quinolin-8-yl-oxy)acetic acid ligand. The angles around the Hg atom vary from 100.31 (15) to 152.65 (4)°. Two additional Hg⋯O inter-actions [2.739 (1) and 2.905 (1) Å] complete the coordination sphere about the Hg(II) atom.

Related literature

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

Experimental

Crystal data

[HgBr2(C12H11NO3)]

M = 577.63

Triclinic,

a = 7.3132 (8) Å

b = 9.9385 (10) Å

c = 10.9902 (10) Å

α = 72.102 (11)°

β = 74.966 (12)°

γ = 70.740 (11)°

V = 706.40 (14) Å3

Z = 2

Mo Kα radiation

μ = 16.55 mm−1

T = 223 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.044, T max = 0.137

6021 measured reflections

2599 independent reflections

1949 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.074

S = 0.80

2599 reflections

174 parameters

H-atom parameters constrained

Δρmax = 2.41 e Å−3

Δρmin = −2.04 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/S1600536812028085/gg2082sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028085/gg2082Isup2.hkl

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

[HgBr2(C12H11NO3)]	Z = 2
Mr = 577.63	F(000) = 528
Triclinic, P1	Dx = 2.716 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.3132 (8) Å	Cell parameters from 3544 reflections
b = 9.9385 (10) Å	θ = 3.2–27.5°
c = 10.9902 (10) Å	µ = 16.55 mm−1
α = 72.102 (11)°	T = 223 K
β = 74.966 (12)°	Prism, colorless
γ = 70.740 (11)°	0.50 × 0.40 × 0.20 mm
V = 706.40 (14) Å3

Rigaku Saturn diffractometer	2599 independent reflections
Radiation source: fine-focus sealed tube	1949 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −11→12
Tmin = 0.044, Tmax = 0.137	l = −12→13
6021 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 0.80	w = 1/[σ2(Fo2) + (0.0232P)2] where P = (Fo2 + 2Fc2)/3
2599 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 2.41 e Å−3
0 restraints	Δρmin = −2.04 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	1.01854 (5)	0.82765 (4)	0.67755 (3)	0.02656 (13)
Br1	1.28595 (13)	0.77673 (12)	0.79728 (8)	0.0324 (3)
Br2	0.72668 (13)	0.98864 (11)	0.58446 (8)	0.0316 (3)
O1	0.9081 (8)	0.5789 (7)	0.8222 (5)	0.0260 (15)
O2	0.5235 (8)	0.7032 (7)	1.0669 (5)	0.0303 (16)
O3	0.7280 (9)	0.8198 (7)	0.9145 (6)	0.0311 (16)
N1	1.1332 (9)	0.6134 (8)	0.5841 (6)	0.0211 (17)
C1	1.2348 (12)	0.6300 (10)	0.4657 (8)	0.023 (2)
H1	1.2428	0.7252	0.4193	0.028*
C2	1.3332 (12)	0.5136 (11)	0.4032 (8)	0.029 (2)
H2	1.4003	0.5321	0.3170	0.035*
C3	1.3281 (12)	0.3746 (11)	0.4709 (8)	0.026 (2)
H3	1.3952	0.2947	0.4330	0.032*
C4	1.2191 (11)	0.3517 (10)	0.6005 (7)	0.020 (2)
C5	1.2060 (12)	0.2104 (10)	0.6737 (9)	0.029 (2)
H5	1.2722	0.1280	0.6392	0.035*
C6	1.0952 (13)	0.1947 (11)	0.7963 (9)	0.033 (3)
H6	1.0871	0.1005	0.8461	0.040*
C7	0.9956 (12)	0.3148 (11)	0.8475 (8)	0.026 (2)
H7	0.9182	0.3007	0.9309	0.031*
C8	1.0058 (11)	0.4532 (10)	0.7809 (8)	0.021 (2)
C9	1.1234 (11)	0.4738 (10)	0.6524 (8)	0.019 (2)
C10	0.7609 (12)	0.5656 (11)	0.9358 (8)	0.027 (2)
H10A	0.8196	0.4930	1.0083	0.033*
H10B	0.6588	0.5320	0.9205	0.033*
C11	0.6734 (13)	0.7084 (12)	0.9681 (8)	0.031 (3)
C12	0.4182 (13)	0.8376 (12)	1.1065 (9)	0.041 (3)
H12A	0.5058	0.8692	1.1378	0.062*
H12B	0.3083	0.8212	1.1754	0.062*
H12C	0.3696	0.9130	1.0331	0.062*

	U11	U22	U33	U12	U13	U23
Hg1	0.0287 (2)	0.0224 (2)	0.02744 (19)	−0.00666 (15)	−0.00615 (14)	−0.00383 (15)
Br1	0.0335 (5)	0.0360 (7)	0.0283 (5)	−0.0116 (5)	−0.0083 (4)	−0.0042 (4)
Br2	0.0288 (5)	0.0271 (6)	0.0362 (5)	−0.0052 (4)	−0.0077 (4)	−0.0051 (4)
O1	0.031 (3)	0.021 (4)	0.022 (3)	−0.012 (3)	0.010 (3)	−0.008 (3)
O2	0.036 (3)	0.029 (4)	0.023 (3)	−0.013 (3)	0.014 (3)	−0.014 (3)
O3	0.040 (4)	0.017 (4)	0.032 (3)	−0.009 (3)	0.005 (3)	−0.008 (3)
N1	0.020 (4)	0.028 (5)	0.018 (4)	−0.012 (3)	0.003 (3)	−0.008 (3)
C1	0.027 (5)	0.019 (6)	0.028 (5)	−0.010 (4)	−0.012 (4)	−0.001 (4)
C2	0.025 (5)	0.036 (7)	0.028 (5)	−0.013 (5)	−0.002 (4)	−0.007 (5)
C3	0.019 (4)	0.031 (6)	0.034 (5)	0.000 (4)	−0.009 (4)	−0.018 (5)
C4	0.014 (4)	0.021 (6)	0.022 (4)	−0.002 (4)	−0.001 (3)	−0.005 (4)
C5	0.033 (5)	0.014 (6)	0.043 (5)	0.000 (4)	−0.010 (4)	−0.014 (4)
C6	0.040 (6)	0.023 (6)	0.033 (5)	−0.014 (5)	−0.005 (4)	0.002 (5)
C7	0.024 (5)	0.025 (6)	0.025 (5)	−0.002 (4)	−0.001 (4)	−0.010 (4)
C8	0.018 (4)	0.021 (6)	0.026 (4)	−0.006 (4)	−0.003 (3)	−0.010 (4)
C9	0.016 (4)	0.019 (6)	0.024 (4)	−0.003 (4)	−0.006 (3)	−0.007 (4)
C10	0.025 (5)	0.028 (6)	0.027 (5)	−0.006 (4)	0.000 (4)	−0.009 (4)
C11	0.029 (5)	0.046 (8)	0.017 (4)	−0.013 (5)	−0.007 (4)	0.000 (5)
C12	0.034 (5)	0.038 (8)	0.047 (6)	−0.012 (5)	0.009 (5)	−0.015 (5)

Hg1—Br1	2.4667 (9)	C4—C9	1.396 (13)
Hg1—Br2	2.4569 (10)	C4—C5	1.409 (12)
Hg1—N1	2.451 (8)	C5—C6	1.372 (12)
O1—C8	1.367 (11)	C5—H5	0.9400
O1—C10	1.425 (9)	C6—C7	1.378 (14)
O2—C11	1.330 (10)	C6—H6	0.9400
O2—C12	1.440 (12)	C7—C8	1.362 (12)
O3—C11	1.225 (11)	C7—H7	0.9400
N1—C1	1.312 (10)	C8—C9	1.444 (11)
N1—C9	1.375 (11)	C10—C11	1.463 (14)
C1—C2	1.418 (14)	C10—H10A	0.9800
C1—H1	0.9400	C10—H10B	0.9800
C2—C3	1.361 (12)	C12—H12A	0.9700
C2—H2	0.9400	C12—H12B	0.9700
C3—C4	1.431 (11)	C12—H12C	0.9700
C3—H3	0.9400
N1—Hg1—Br2	106.34 (15)	C7—C6—H6	119.5
N1—Hg1—Br1	100.31 (15)	C8—C7—C6	122.0 (8)
Br2—Hg1—Br1	152.65 (4)	C8—C7—H7	119.0
C8—O1—C10	116.2 (7)	C6—C7—H7	119.0
C11—O2—C12	117.3 (8)	C7—C8—O1	126.1 (8)
C1—N1—C9	117.8 (8)	C7—C8—C9	118.6 (9)
C1—N1—Hg1	116.8 (6)	O1—C8—C9	115.3 (7)
C9—N1—Hg1	124.7 (5)	N1—C9—C4	122.2 (7)
N1—C1—C2	124.2 (8)	N1—C9—C8	119.0 (8)
N1—C1—H1	117.9	C4—C9—C8	118.8 (8)
C2—C1—H1	117.9	O1—C10—C11	109.4 (7)
C3—C2—C1	118.5 (9)	O1—C10—H10A	109.8
C3—C2—H2	120.8	C11—C10—H10A	109.8
C1—C2—H2	120.8	O1—C10—H10B	109.8
C2—C3—C4	119.0 (10)	C11—C10—H10B	109.8
C2—C3—H3	120.5	H10A—C10—H10B	108.2
C4—C3—H3	120.5	O3—C11—O2	122.8 (10)
C9—C4—C5	120.5 (8)	O3—C11—C10	126.2 (8)
C9—C4—C3	118.2 (8)	O2—C11—C10	111.0 (8)
C5—C4—C3	121.3 (9)	O2—C12—H12A	109.5
C6—C5—C4	119.1 (9)	O2—C12—H12B	109.5
C6—C5—H5	120.5	H12A—C12—H12B	109.5
C4—C5—H5	120.5	O2—C12—H12C	109.5
C5—C6—C7	121.0 (9)	H12A—C12—H12C	109.5
C5—C6—H6	119.5	H12B—C12—H12C	109.5
Br2—Hg1—N1—C1	79.0 (6)	C1—N1—C9—C4	0.9 (11)
Br1—Hg1—N1—C1	−94.8 (6)	Hg1—N1—C9—C4	−169.3 (6)
Br2—Hg1—N1—C9	−110.8 (6)	C1—N1—C9—C8	−177.4 (7)
Br1—Hg1—N1—C9	75.4 (6)	Hg1—N1—C9—C8	12.4 (10)
C9—N1—C1—C2	0.7 (12)	C5—C4—C9—N1	179.8 (7)
Hg1—N1—C1—C2	171.6 (6)	C3—C4—C9—N1	−1.0 (11)
N1—C1—C2—C3	−2.1 (13)	C5—C4—C9—C8	−1.9 (12)
C1—C2—C3—C4	1.9 (12)	C3—C4—C9—C8	177.3 (7)
C2—C3—C4—C9	−0.5 (11)	C7—C8—C9—N1	179.5 (7)
C2—C3—C4—C5	178.7 (7)	O1—C8—C9—N1	1.8 (11)
C9—C4—C5—C6	1.0 (12)	C7—C8—C9—C4	1.1 (11)
C3—C4—C5—C6	−178.2 (8)	O1—C8—C9—C4	−176.5 (7)
C4—C5—C6—C7	0.8 (14)	C8—O1—C10—C11	179.0 (7)
C5—C6—C7—C8	−1.6 (14)	C12—O2—C11—O3	2.8 (12)
C6—C7—C8—O1	178.0 (8)	C12—O2—C11—C10	−177.8 (7)
C6—C7—C8—C9	0.6 (13)	O1—C10—C11—O3	−6.2 (12)
C10—O1—C8—C7	−9.9 (12)	O1—C10—C11—O2	174.5 (6)
C10—O1—C8—C9	167.5 (7)

Table 1

Selected bond lengths (Å)

Hg1—Br1	2.4667 (9)
Hg1—Br2	2.4569 (10)
Hg1—N1	2.451 (8)