Di-μ-chlorido-bis-{chlorido[4-nitro-N-(pyridin-2-yl-methyl-idene-κN)aniline-κN]mercury(II)}.

In the centrosymmetric dinuclear title complex, [Hg(2)Cl(4)(C(12)H(9)N(3)O(2))(2)], the Hg(II) ion is in a distorted square-pyramidal coordination environment formed by the N atoms of the diimine ligand, two bridging Cl atoms and one terminal Cl atom. One of the bridging Hg-Cl bonds is significantly longer than the other.

Related literature

For background to diimine complexes and related structures, see: Dehghanpour et al. (2007 ▶); Mahmoudi et al. (2009 ▶).

Experimental

Crystal data

[Hg2Cl4(C12H9N3O2)2]

M = 997.42

Monoclinic,

a = 8.9731 (2) Å

b = 7.8439 (3) Å

c = 20.1403 (7) Å

β = 98.155 (2)°

V = 1403.22 (8) Å3

Z = 2

Mo Kα radiation

μ = 11.35 mm−1

T = 150 K

0.18 × 0.16 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.115, T max = 0.222

11428 measured reflections

3197 independent reflections

2639 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.06

3197 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −1.56 e Å−3

Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004703/gk2347sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004703/gk2347Isup2.hkl

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

[Hg2Cl4(C12H9N3O2)2]	F(000) = 928
Mr = 997.42	Dx = 2.361 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6448 reflections
a = 8.9731 (2) Å	θ = 2.6–27.5°
b = 7.8439 (3) Å	µ = 11.35 mm−1
c = 20.1403 (7) Å	T = 150 K
β = 98.155 (2)°	Block, colourless
V = 1403.22 (8) Å3	0.18 × 0.16 × 0.14 mm
Z = 2

Nonius KappaCCD diffractometer	3197 independent reflections
Radiation source: fine-focus sealed tube	2639 reflections with I > 2σ(I)
graphite	Rint = 0.055
Detector resolution: 9 pixels mm-1	θmax = 27.6°, θmin = 2.8°
φ scans and ω scans with κ offsets	h = −11→11
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −9→10
Tmin = 0.115, Tmax = 0.222	l = −25→26
11428 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0234P)2 + 1.6835P] where P = (Fo2 + 2Fc2)/3
3197 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −1.56 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	0.641245 (19)	0.62356 (2)	0.448116 (9)	0.02542 (8)
Cl1	0.83299 (13)	0.45830 (16)	0.40698 (7)	0.0314 (3)
Cl2	0.60508 (13)	0.60053 (14)	0.56941 (6)	0.0270 (3)
O1	1.0314 (4)	1.2850 (5)	0.72381 (19)	0.0428 (9)
O2	1.1963 (4)	1.0918 (5)	0.7078 (2)	0.0440 (10)
N1	0.5013 (4)	0.7782 (5)	0.36266 (19)	0.0238 (8)
N2	0.6929 (4)	0.9273 (5)	0.4652 (2)	0.0216 (8)
N3	1.0753 (5)	1.1652 (5)	0.6919 (2)	0.0319 (10)
C1	0.4077 (5)	0.7090 (6)	0.3123 (2)	0.0265 (10)
H1A	0.3985	0.5884	0.3101	0.032*
C2	0.3234 (5)	0.8064 (7)	0.2632 (3)	0.0308 (11)
H2A	0.2589	0.7531	0.2277	0.037*
C3	0.3344 (5)	0.9808 (7)	0.2663 (3)	0.0312 (11)
H3A	0.2769	1.0502	0.2335	0.037*
C4	0.4315 (5)	1.0539 (6)	0.3187 (2)	0.0275 (10)
H4A	0.4404	1.1744	0.3222	0.033*
C5	0.5152 (5)	0.9497 (6)	0.3657 (2)	0.0212 (9)
C6	0.6209 (5)	1.0210 (6)	0.4202 (3)	0.0228 (10)
H6A	0.6364	1.1408	0.4221	0.027*
C7	0.7901 (5)	0.9952 (6)	0.5209 (2)	0.0206 (9)
C8	0.7776 (5)	1.1611 (6)	0.5433 (2)	0.0239 (10)
H8A	0.7039	1.2351	0.5203	0.029*
C9	0.8717 (5)	1.2189 (6)	0.5988 (2)	0.0265 (10)
H9A	0.8641	1.3324	0.6145	0.032*
C10	0.9778 (5)	1.1072 (6)	0.6314 (2)	0.0242 (10)
C11	0.9934 (5)	0.9425 (6)	0.6092 (2)	0.0257 (10)
H11A	1.0688	0.8696	0.6316	0.031*
C12	0.8981 (5)	0.8855 (6)	0.5542 (2)	0.0241 (10)
H12A	0.9058	0.7717	0.5388	0.029*

	U11	U22	U33	U12	U13	U23
Hg1	0.03088 (12)	0.01758 (11)	0.02789 (12)	0.00384 (7)	0.00446 (8)	0.00096 (8)
Cl1	0.0311 (6)	0.0273 (6)	0.0363 (7)	0.0085 (5)	0.0069 (5)	−0.0012 (5)
Cl2	0.0332 (6)	0.0244 (6)	0.0233 (6)	−0.0052 (4)	0.0035 (5)	−0.0015 (5)
O1	0.037 (2)	0.046 (2)	0.043 (2)	−0.0073 (18)	0.0020 (17)	−0.017 (2)
O2	0.0277 (19)	0.055 (3)	0.045 (2)	0.0031 (17)	−0.0075 (16)	−0.0044 (19)
N1	0.0249 (19)	0.022 (2)	0.025 (2)	0.0021 (16)	0.0057 (16)	0.0018 (17)
N2	0.0210 (18)	0.0192 (19)	0.025 (2)	0.0007 (15)	0.0039 (15)	0.0047 (16)
N3	0.026 (2)	0.037 (3)	0.033 (3)	−0.0090 (18)	0.0047 (18)	−0.003 (2)
C1	0.029 (2)	0.026 (3)	0.024 (3)	−0.003 (2)	0.0052 (19)	0.001 (2)
C2	0.029 (2)	0.035 (3)	0.026 (3)	−0.004 (2)	−0.004 (2)	−0.004 (2)
C3	0.033 (3)	0.036 (3)	0.023 (3)	0.012 (2)	0.000 (2)	0.006 (2)
C4	0.035 (3)	0.021 (2)	0.026 (3)	0.004 (2)	0.003 (2)	0.001 (2)
C5	0.026 (2)	0.021 (2)	0.017 (2)	0.0034 (19)	0.0048 (18)	0.0020 (19)
C6	0.027 (2)	0.013 (2)	0.029 (3)	0.0024 (18)	0.0064 (19)	−0.001 (2)
C7	0.019 (2)	0.019 (2)	0.024 (3)	0.0006 (17)	0.0067 (18)	0.0006 (19)
C8	0.025 (2)	0.022 (2)	0.024 (3)	0.0018 (18)	0.0044 (19)	0.0039 (19)
C9	0.025 (2)	0.020 (2)	0.035 (3)	−0.0029 (19)	0.009 (2)	−0.006 (2)
C10	0.020 (2)	0.026 (3)	0.027 (3)	−0.0062 (18)	0.0036 (18)	−0.002 (2)
C11	0.024 (2)	0.023 (2)	0.030 (3)	0.004 (2)	0.0027 (19)	0.004 (2)
C12	0.022 (2)	0.020 (2)	0.031 (3)	−0.0005 (18)	0.0053 (19)	−0.001 (2)

Hg1—N1	2.323 (4)	C3—C4	1.392 (7)
Hg1—Cl1	2.3940 (11)	C3—H3A	0.9500
Hg1—N2	2.442 (4)	C4—C5	1.388 (6)
Hg1—Cl2	2.5161 (12)	C4—H4A	0.9500
Hg1—Cl2i	2.8068 (11)	C5—C6	1.457 (6)
Cl2—Hg1i	2.8068 (11)	C6—H6A	0.9500
O1—N3	1.233 (5)	C7—C8	1.387 (6)
O2—N3	1.231 (5)	C7—C12	1.394 (6)
N1—C1	1.337 (6)	C8—C9	1.380 (7)
N1—C5	1.352 (6)	C8—H8A	0.9500
N2—C6	1.272 (6)	C9—C10	1.388 (7)
N2—C7	1.423 (6)	C9—H9A	0.9500
N3—C10	1.468 (6)	C10—C11	1.381 (6)
C1—C2	1.386 (7)	C11—C12	1.375 (7)
C1—H1A	0.9500	C11—H11A	0.9500
C2—C3	1.372 (7)	C12—H12A	0.9500
C2—H2A	0.9500
N1—Hg1—Cl1	111.46 (10)	C4—C3—H3A	120.7
N1—Hg1—N2	70.57 (13)	C5—C4—C3	119.6 (5)
Cl1—Hg1—N2	116.47 (9)	C5—C4—H4A	120.2
N1—Hg1—Cl2	128.76 (9)	C3—C4—H4A	120.2
Cl1—Hg1—Cl2	119.68 (4)	N1—C5—C4	121.2 (4)
N2—Hg1—Cl2	88.91 (9)	N1—C5—C6	117.6 (4)
N1—Hg1—Cl2i	84.28 (9)	C4—C5—C6	121.3 (4)
Cl1—Hg1—Cl2i	102.07 (4)	N2—C6—C5	121.8 (4)
N2—Hg1—Cl2i	139.38 (9)	N2—C6—H6A	119.1
Cl2—Hg1—Cl2i	82.50 (4)	C5—C6—H6A	119.1
Hg1—Cl2—Hg1i	97.50 (4)	C8—C7—C12	120.4 (4)
C1—N1—C5	118.8 (4)	C8—C7—N2	122.6 (4)
C1—N1—Hg1	124.5 (3)	C12—C7—N2	117.0 (4)
C5—N1—Hg1	116.7 (3)	C9—C8—C7	120.2 (4)
C6—N2—C7	122.6 (4)	C9—C8—H8A	119.9
C6—N2—Hg1	113.3 (3)	C7—C8—H8A	119.9
C7—N2—Hg1	124.0 (3)	C8—C9—C10	118.4 (4)
O2—N3—O1	123.8 (4)	C8—C9—H9A	120.8
O2—N3—C10	118.1 (4)	C10—C9—H9A	120.8
O1—N3—C10	118.1 (4)	C11—C10—C9	122.2 (4)
N1—C1—C2	122.6 (5)	C11—C10—N3	118.9 (4)
N1—C1—H1A	118.7	C9—C10—N3	119.0 (4)
C2—C1—H1A	118.7	C12—C11—C10	119.0 (4)
C3—C2—C1	119.2 (5)	C12—C11—H11A	120.5
C3—C2—H2A	120.4	C10—C11—H11A	120.5
C1—C2—H2A	120.4	C11—C12—C7	119.8 (4)
C2—C3—C4	118.6 (4)	C11—C12—H12A	120.1
C2—C3—H3A	120.7	C7—C12—H12A	120.1
N1—Hg1—Cl2—Hg1i	76.43 (12)	C1—N1—C5—C6	−178.4 (4)
Cl1—Hg1—Cl2—Hg1i	−99.66 (5)	Hg1—N1—C5—C6	2.7 (5)
N2—Hg1—Cl2—Hg1i	140.20 (9)	C3—C4—C5—N1	−1.8 (7)
Cl2i—Hg1—Cl2—Hg1i	0.0	C3—C4—C5—C6	178.4 (4)
Cl1—Hg1—N1—C1	68.2 (4)	C7—N2—C6—C5	−176.3 (4)
N2—Hg1—N1—C1	179.9 (4)	Hg1—N2—C6—C5	1.9 (5)
Cl2—Hg1—N1—C1	−108.1 (3)	N1—C5—C6—N2	−3.2 (6)
Cl2i—Hg1—N1—C1	−32.5 (3)	C4—C5—C6—N2	176.7 (4)
Cl1—Hg1—N1—C5	−112.9 (3)	C6—N2—C7—C8	22.2 (7)
N2—Hg1—N1—C5	−1.3 (3)	Hg1—N2—C7—C8	−155.9 (3)
Cl2—Hg1—N1—C5	70.7 (3)	C6—N2—C7—C12	−159.7 (4)
Cl2i—Hg1—N1—C5	146.3 (3)	Hg1—N2—C7—C12	22.3 (5)
N1—Hg1—N2—C6	−0.3 (3)	C12—C7—C8—C9	−0.2 (7)
Cl1—Hg1—N2—C6	104.6 (3)	N2—C7—C8—C9	177.9 (4)
Cl2—Hg1—N2—C6	−132.5 (3)	C7—C8—C9—C10	−0.2 (7)
Cl2i—Hg1—N2—C6	−55.3 (4)	C8—C9—C10—C11	1.2 (7)
N1—Hg1—N2—C7	177.8 (3)	C8—C9—C10—N3	−177.9 (4)
Cl1—Hg1—N2—C7	−77.2 (3)	O2—N3—C10—C11	23.7 (6)
Cl2—Hg1—N2—C7	45.7 (3)	O1—N3—C10—C11	−156.4 (4)
Cl2i—Hg1—N2—C7	122.8 (3)	O2—N3—C10—C9	−157.1 (4)
C5—N1—C1—C2	−0.4 (7)	O1—N3—C10—C9	22.7 (6)
Hg1—N1—C1—C2	178.4 (3)	C9—C10—C11—C12	−1.8 (7)
N1—C1—C2—C3	−0.8 (7)	N3—C10—C11—C12	177.3 (4)
C1—C2—C3—C4	0.7 (7)	C10—C11—C12—C7	1.4 (7)
C2—C3—C4—C5	0.5 (7)	C8—C7—C12—C11	−0.5 (7)
C1—N1—C5—C4	1.7 (6)	N2—C7—C12—C11	−178.7 (4)
Hg1—N1—C5—C4	−177.2 (3)

Table 1

Selected bond lengths (Å)

Hg1—N1	2.323 (4)
Hg1—Cl1	2.3940 (11)
Hg1—N2	2.442 (4)
Hg1—Cl2	2.5161 (12)
Hg1—Cl2i	2.8068 (11)

Symmetry code: (i) .