(4,5-Diaza-fluoren-9-one-κN,N')bis-(thio-cyanato-κS)mercury(II).

In the title compound, [Hg(NCS)(2)(C(11)H(6)N(2)O)], the Hg(II) atom, lying on a twofold rotation axis, is four-coordinated in a distorted tetra-hedral geometry by an N,N'-bidentate diaza-fluoren-9-one ligand and two thio-cyanate anions. In the crystal, inter-molecular C-H⋯N and C-H⋯O hydrogen bonds are effective in the stabilization of the structure.

Related literature

For general background to metal complexes with diaza­fluoren-9-one ligands, see: Biju & Rajasekharan (2008 ▶); Kulkarni et al. (2002 ▶); Menon & Rajasekharan (1998 ▶); Shi et al. (1995 ▶); Wu & Xu (2004 ▶); Zhang et al. (2004 ▶). For related structures, see: Ravikumar & Lakshmi (1994 ▶); Safari et al. (2009 ▶). For the synthesis of the ligand, see: Henderson et al. (1984 ▶).

Experimental

Crystal data

[Hg(NCS)2(C11H6N2O)]

M = 498.95

Monoclinic,

a = 10.570 (2) Å

b = 16.112 (3) Å

c = 8.3390 (17) Å

β = 94.35 (3)°

V = 1416.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 11.17 mm−1

T = 298 K

0.45 × 0.30 × 0.25 mm

Data collection

Stoe IPDS-2T diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.023, T max = 0.059

4787 measured reflections

1903 independent reflections

1737 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.09

1903 reflections

97 parameters

H-atom parameters constrained

Δρmax = 4.61 e Å−3

Δρmin = −1.82 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008142/hy2412sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008142/hy2412Isup2.hkl

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

[Hg(NCS)2(C11H6N2O)]	F(000) = 928
Mr = 498.95	Dx = 2.340 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1903 reflections
a = 10.570 (2) Å	θ = 2.3–29.1°
b = 16.112 (3) Å	µ = 11.17 mm−1
c = 8.3390 (17) Å	T = 298 K
β = 94.35 (3)°	Block, yellow
V = 1416.1 (5) Å3	0.45 × 0.30 × 0.25 mm
Z = 4

Stoe IPDS-2T diffractometer	1903 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
graphite	Rint = 0.098
ω scans	θmax = 29.1°, θmin = 2.3°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −14→14
Tmin = 0.023, Tmax = 0.059	k = −19→22
4787 measured reflections	l = −11→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/3
1903 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 4.61 e Å−3
0 restraints	Δρmin = −1.81 e Å−3

	x	y	z	Uiso*/Ueq
C7	0.7118 (6)	0.0950 (5)	0.0048 (8)	0.0493 (13)
Hg1	0.5000	0.072315 (18)	0.2500	0.04567 (15)
N1	0.4449 (4)	0.1960 (3)	0.0815 (6)	0.0365 (9)
C1	0.4721 (4)	0.2635 (3)	0.1663 (6)	0.0320 (9)
C2	0.3956 (5)	0.2094 (4)	−0.0707 (7)	0.0422 (11)
H2	0.3735	0.1637	−0.1350	0.051*
C5	0.4558 (5)	0.3449 (3)	0.1142 (7)	0.0377 (10)
C3	0.3766 (6)	0.2879 (4)	−0.1349 (7)	0.0453 (12)
H3	0.3438	0.2937	−0.2409	0.054*
C4	0.4063 (5)	0.3591 (4)	−0.0419 (8)	0.0456 (12)
H4	0.3935	0.4124	−0.0827	0.055*
S1	0.68555 (17)	0.01847 (11)	0.1348 (2)	0.0576 (4)
O1	0.5000	0.4758 (4)	0.2500	0.0586 (17)
C6	0.5000	0.4016 (6)	0.2500	0.0432 (17)
N2	0.7356 (8)	0.1448 (6)	−0.0831 (10)	0.083 (2)

	U11	U22	U33	U12	U13	U23
C7	0.049 (3)	0.058 (4)	0.041 (3)	0.004 (3)	0.005 (2)	−0.002 (3)
Hg1	0.0541 (2)	0.03049 (19)	0.0543 (2)	0.000	0.01618 (14)	0.000
N1	0.0374 (19)	0.029 (2)	0.043 (2)	0.0004 (16)	0.0032 (16)	0.0006 (17)
C1	0.0334 (19)	0.022 (2)	0.040 (3)	0.0006 (16)	0.0044 (17)	0.0012 (16)
C2	0.046 (3)	0.040 (3)	0.040 (3)	0.004 (2)	0.002 (2)	0.001 (2)
C5	0.035 (2)	0.028 (2)	0.050 (3)	0.0014 (18)	0.0046 (19)	0.005 (2)
C3	0.046 (3)	0.047 (3)	0.043 (3)	0.007 (2)	0.005 (2)	0.007 (2)
C4	0.046 (3)	0.035 (3)	0.056 (3)	0.005 (2)	0.006 (2)	0.015 (2)
S1	0.0623 (9)	0.0412 (8)	0.0715 (11)	0.0171 (7)	0.0201 (8)	0.0072 (7)
O1	0.072 (4)	0.023 (3)	0.081 (5)	0.000	0.007 (4)	0.000
C6	0.038 (3)	0.033 (4)	0.060 (5)	0.000	0.011 (3)	0.000
N2	0.077 (4)	0.104 (7)	0.070 (5)	0.003 (4)	0.021 (3)	0.025 (4)

C7—N2	1.128 (11)	C2—H2	0.9300
C7—S1	1.679 (8)	C5—C4	1.385 (8)
Hg1—S1	2.4098 (17)	C5—C6	1.502 (8)
Hg1—N1	2.483 (5)	C3—C4	1.407 (9)
N1—C1	1.316 (7)	C3—H3	0.9300
N1—C2	1.352 (7)	C4—H4	0.9300
C1—C5	1.388 (6)	O1—C6	1.195 (12)
C1—C1i	1.473 (10)	C6—C5i	1.502 (8)
C2—C3	1.382 (8)
N2—C7—S1	176.4 (8)	C3—C2—H2	118.5
S1i—Hg1—S1	137.80 (9)	C4—C5—C1	118.7 (5)
S1i—Hg1—N1i	103.08 (11)	C4—C5—C6	132.9 (5)
S1—Hg1—N1i	110.60 (12)	C1—C5—C6	108.4 (5)
S1i—Hg1—N1	110.60 (12)	C2—C3—C4	120.9 (5)
S1—Hg1—N1	103.08 (11)	C2—C3—H3	119.6
N1i—Hg1—N1	73.2 (2)	C4—C3—H3	119.6
C1—N1—C2	115.2 (5)	C5—C4—C3	115.8 (5)
C1—N1—Hg1	109.0 (3)	C5—C4—H4	122.1
C2—N1—Hg1	135.7 (4)	C3—C4—H4	122.1
N1—C1—C5	126.5 (5)	C7—S1—Hg1	99.9 (2)
N1—C1—C1i	124.4 (3)	O1—C6—C5i	127.5 (4)
C5—C1—C1i	109.1 (3)	O1—C6—C5	127.5 (4)
N1—C2—C3	122.9 (6)	C5i—C6—C5	105.0 (7)
N1—C2—H2	118.5
S1i—Hg1—N1—C1	97.7 (3)	N1—C1—C5—C6	−179.7 (4)
S1—Hg1—N1—C1	−108.1 (3)	C1i—C1—C5—C6	−0.8 (6)
N1i—Hg1—N1—C1	−0.3 (2)	N1—C2—C3—C4	−1.1 (9)
S1i—Hg1—N1—C2	−82.2 (5)	C1—C5—C4—C3	0.0 (8)
S1—Hg1—N1—C2	71.9 (5)	C6—C5—C4—C3	179.5 (5)
N1i—Hg1—N1—C2	179.8 (6)	C2—C3—C4—C5	0.6 (9)
C2—N1—C1—C5	−0.5 (8)	S1i—Hg1—S1—C7	150.1 (3)
Hg1—N1—C1—C5	179.5 (4)	N1i—Hg1—S1—C7	−69.2 (3)
C2—N1—C1—C1i	−179.2 (6)	N1—Hg1—S1—C7	7.5 (3)
Hg1—N1—C1—C1i	0.8 (7)	C4—C5—C6—O1	0.7 (7)
C1—N1—C2—C3	1.1 (8)	C1—C5—C6—O1	−179.7 (3)
Hg1—N1—C2—C3	−179.0 (4)	C4—C5—C6—C5i	−179.3 (7)
N1—C1—C5—C4	0.0 (8)	C1—C5—C6—C5i	0.3 (3)
C1i—C1—C5—C4	178.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2ii	0.93	2.56	3.276 (10)	134
C4—H4···O1iii	0.93	2.59	3.366 (8)	142

Table 1

Selected bond lengths (Å)

Hg1—S1	2.4098 (17)
Hg1—N1	2.483 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2i	0.93	2.56	3.276 (10)	134
C4—H4⋯O1ii	0.93	2.59	3.366 (8)	142

Symmetry codes: (i) ; (ii) .