catena-Poly[[dipyridine-mercury(II)]-μ-5-amino-2,4,6-triiodo-isophthalato].

The reaction of mercury(II) chloride with 5-amino-2,4,6-triiodo-isophthalic acid in pyridine solution leads to the formation of the title compound, [Hg(C(8)H(2)I(3)NO(4))(C(5)H(5)N)(2)](n). The structure contains a four-coordinate Hg(2+) ion in a distorted tetra-hedral geometry, which lies on a crystallographic twofold axis. The Hg(2+) ion is bonded to two N atoms from two pyridine ligands and two carboxylate O atoms from two 5-amino-2,4,6-triiodo-isophthalate anions. The two carboxyl-ate groups of individual 5-amino-2,4,6-triiodo-isophthalate anions act as a bridge to the Hg centers. This anion also resides on a twofold axis, which passes through the amino N and the trans standing I atoms. The Hg-O distance is 2.337 (6) and the Hg-N distance is 2.244 (8) Å.

Related literature

For general background, see: Ziegler et al. (1997 ▶). For related structures, see: Bebout et al. (1998 ▶); Beck & Sheldrick (2008 ▶); Matković-Čalogović et al. (2002 ▶); Weil (2001 ▶).

Experimental

Crystal data

[Hg(C8H2I3NO4)(C5H5N)2]

M = 915.60

Tetragonal,

a = 11.9338 (3) Å

c = 16.0532 (10) Å

V = 2286.23 (16) Å3

Z = 4

Mo Kα radiation

μ = 10.81 mm−1

T = 296 (2) K

0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.16, T max = 0.20

10399 measured reflections

2251 independent reflections

1661 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.067

S = 1.06

2251 reflections

134 parameters

57 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983 ▶), 897 Friedel pairs

Flack parameter: 0.010 (9)

Data collection: APEX2 (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 I, global. DOI: 10.1107/S1600536808030468/fj2148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030468/fj2148Isup2.hkl

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

[Hg(C8H2I3NO4)(C5H5N)2]	Dx = 2.660 Mg m−3
Mr = 915.60	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 2411 reflections
Hall symbol: P 4abw 2nw	θ = 2.1–25.1°
a = 11.9338 (3) Å	µ = 10.81 mm−1
c = 16.0532 (10) Å	T = 296 K
V = 2286.23 (16) Å3	Pyramid, colorless
Z = 4	0.20 × 0.15 × 0.15 mm
F(000) = 1648

Bruker SMART APEX CCD diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1661 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→14
Tmin = 0.16, Tmax = 0.20	k = −14→12
10399 measured reflections	l = −19→13

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0151P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2251 reflections	Δρmax = 0.63 e Å−3
134 parameters	Δρmin = −0.53 e Å−3
57 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (9)

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	Occ. (<1)
C1	0.6137 (6)	0.3863 (6)	0.7500	0.036 (2)
C2	0.6218 (7)	0.3118 (6)	0.6838 (5)	0.041 (2)
C3	0.7046 (7)	0.2319 (7)	0.6843 (5)	0.046 (2)
C4	0.7809 (7)	0.2191 (7)	0.7500	0.049 (3)
C5	0.5357 (7)	0.3173 (8)	0.6152 (6)	0.051 (2)
C6	0.4694 (10)	0.1635 (9)	0.4089 (8)	0.097 (2)
H6	0.5308	0.1844	0.4410	0.116*
C7	0.4795 (12)	0.0725 (11)	0.3565 (8)	0.112 (2)
H7	0.5451	0.0305	0.3549	0.134*
C8	0.3905 (11)	0.0459 (11)	0.3071 (9)	0.118 (2)
H8	0.3965	−0.0087	0.2660	0.142*
C9	0.2919 (11)	0.1019 (10)	0.3198 (8)	0.111 (2)
H9	0.2264	0.0787	0.2937	0.133*
C10	0.2919 (10)	0.1900 (10)	0.3703 (8)	0.098 (2)
H10	0.2266	0.2322	0.3738	0.118*
Hg1	0.37049 (3)	0.37049 (3)	0.5000	0.05760 (17)
I1	0.72004 (6)	0.12434 (7)	0.58073 (4)	0.0764 (2)
I3	0.48846 (5)	0.51154 (5)	0.7500	0.0606 (2)
N1	0.8605 (6)	0.1395 (6)	0.7500	0.065 (3)
H1A	0.9060	0.1340	0.7914	0.077*	0.50
H1B	0.8660	0.0940	0.7086	0.077*	0.50
N2	0.3772 (8)	0.2212 (7)	0.4151 (5)	0.0831 (19)
O1	0.4543 (5)	0.2528 (6)	0.6227 (4)	0.0659 (18)
O2	0.5496 (5)	0.3874 (6)	0.5577 (4)	0.0669 (18)

	U11	U22	U33	U12	U13	U23
C1	0.033 (4)	0.033 (4)	0.041 (6)	0.002 (5)	0.006 (4)	0.006 (4)
C2	0.041 (5)	0.043 (5)	0.039 (5)	0.002 (4)	0.011 (5)	0.010 (4)
C3	0.045 (5)	0.049 (5)	0.043 (5)	0.002 (4)	−0.002 (4)	0.000 (4)
C4	0.042 (4)	0.042 (4)	0.062 (8)	0.009 (6)	0.004 (5)	0.004 (5)
C5	0.039 (5)	0.062 (6)	0.051 (6)	0.008 (3)	−0.003 (4)	−0.008 (5)
C6	0.091 (5)	0.089 (5)	0.111 (5)	0.019 (4)	−0.038 (4)	−0.034 (4)
C7	0.104 (5)	0.099 (5)	0.132 (6)	0.027 (4)	−0.041 (4)	−0.043 (4)
C8	0.113 (5)	0.103 (5)	0.138 (6)	0.023 (4)	−0.046 (5)	−0.051 (4)
C9	0.103 (5)	0.096 (5)	0.133 (6)	0.015 (4)	−0.052 (5)	−0.045 (4)
C10	0.092 (5)	0.085 (5)	0.117 (5)	0.014 (4)	−0.046 (4)	−0.033 (4)
Hg1	0.0627 (2)	0.0627 (2)	0.0475 (3)	0.0051 (3)	−0.0068 (2)	0.0068 (2)
I1	0.0676 (4)	0.0958 (6)	0.0658 (5)	0.0210 (4)	0.0003 (4)	−0.0324 (4)
I3	0.0547 (3)	0.0547 (3)	0.0723 (6)	0.0119 (4)	0.0044 (3)	0.0044 (3)
N1	0.070 (4)	0.070 (4)	0.053 (6)	0.004 (7)	−0.004 (4)	−0.004 (4)
N2	0.081 (4)	0.072 (4)	0.097 (4)	0.013 (3)	−0.040 (4)	−0.021 (3)
O1	0.050 (4)	0.077 (5)	0.071 (4)	−0.001 (3)	−0.017 (3)	0.008 (3)
O2	0.068 (4)	0.088 (5)	0.044 (4)	0.001 (4)	−0.006 (3)	0.020 (4)

C1—C2i	1.389 (9)	C8—C9	1.368 (15)
C1—I3	2.113 (9)	C8—H8	0.9300
C2—C3	1.373 (10)	C9—C10	1.327 (15)
C2—C5	1.508 (12)	C9—H9	0.9300
C3—C4	1.402 (10)	C10—N2	1.302 (12)
C3—I1	2.108 (8)	C10—H10	0.9300
C4—N1	1.344 (14)	Hg1—N2	2.244 (8)
C4—C3i	1.402 (10)	Hg1—N2ii	2.244 (8)
C5—O2	1.257 (10)	Hg1—O2ii	2.337 (6)
C5—O1	1.245 (10)	Hg1—O2	2.337 (6)
C5—Hg1	2.777 (9)	Hg1—O1ii	2.618 (6)
C6—N2	1.302 (12)	Hg1—O1	2.618 (6)
C6—C7	1.379 (15)	Hg1—C5ii	2.777 (9)
C6—H6	0.9300	N1—H1A	0.8600
C7—C8	1.363 (15)	N1—H1B	0.8600
C7—H7	0.9300
C2i—C1—C2	119.7 (9)	N2ii—Hg1—O2ii	106.0 (3)
C2i—C1—I3	120.2 (5)	N2—Hg1—O2	106.0 (3)
C2—C1—I3	120.2 (5)	N2ii—Hg1—O2	118.8 (3)
C3—C2—C1	119.4 (8)	O2ii—Hg1—O2	89.9 (3)
C3—C2—C5	121.6 (8)	N2—Hg1—O1ii	82.3 (2)
C1—C2—C5	118.9 (7)	N2ii—Hg1—O1ii	91.0 (3)
C2—C3—C4	123.1 (8)	O2ii—Hg1—O1ii	53.1 (2)
C2—C3—I1	118.8 (6)	O2—Hg1—O1ii	139.1 (2)
C4—C3—I1	118.1 (6)	N2—Hg1—O1	91.0 (3)
N1—C4—C3i	122.4 (5)	N2ii—Hg1—O1	82.3 (2)
N1—C4—C3	122.4 (5)	O2ii—Hg1—O1	139.1 (2)
C3i—C4—C3	115.2 (10)	O2—Hg1—O1	53.1 (2)
O2—C5—O1	125.8 (8)	O1ii—Hg1—O1	167.5 (3)
O2—C5—C2	118.4 (8)	N2—Hg1—C5	101.4 (3)
O1—C5—C2	115.8 (8)	N2ii—Hg1—C5	99.6 (3)
O2—C5—Hg1	56.8 (4)	O2ii—Hg1—C5	114.3 (3)
O1—C5—Hg1	69.6 (5)	O2—Hg1—C5	26.7 (2)
C2—C5—Hg1	168.6 (6)	O1ii—Hg1—C5	165.8 (3)
N2—C6—C7	122.5 (12)	O1—Hg1—C5	26.5 (2)
N2—C6—H6	118.7	N2—Hg1—C5ii	99.6 (3)
C7—C6—H6	118.7	N2ii—Hg1—C5ii	101.4 (3)
C6—C7—C8	118.0 (13)	O2ii—Hg1—C5ii	26.7 (2)
C6—C7—H7	121.0	O2—Hg1—C5ii	114.3 (3)
C8—C7—H7	121.0	O1ii—Hg1—C5ii	26.5 (2)
C9—C8—C7	118.0 (12)	O1—Hg1—C5ii	165.8 (3)
C9—C8—H8	121.0	C5—Hg1—C5ii	140.2 (4)
C7—C8—H8	121.0	C4—N1—H1A	120.0
C10—C9—C8	118.5 (12)	C4—N1—H1B	120.0
C10—C9—H9	120.7	H1A—N1—H1B	120.0
C8—C9—H9	120.7	C6—N2—C10	117.8 (10)
N2—C10—C9	124.4 (12)	C6—N2—Hg1	119.8 (7)
N2—C10—H10	117.8	C10—N2—Hg1	122.4 (7)
C9—C10—H10	117.8	C5—O1—Hg1	83.9 (5)
N2—Hg1—N2ii	115.2 (5)	C5—O2—Hg1	96.5 (5)
N2—Hg1—O2ii	118.8 (3)