Chlorido[1-(2-eth-oxy-phen-yl)3-(4-nitro-phen-yl)triazenido]mercury(II).

In the title compound, [Hg(C(14)H(13)N(4)O(3))Cl], the Hg(II) atom is four-coordinated by one O atom and two N atoms from a tridentate 1-(2-eth-oxy-phen-yl)-3-(4-nitro-phen-yl)triazenide ligand and one terminal chloride ion in a distorted square-planar geometry. In the crystal structure, the mononuclear complexes are linked into pairs through C-H⋯O and C-H⋯Cl hydrogen bonds as well as π-π and C-H⋯π stacking inter-actions. In addition, weak Hg-μ(6)-arene π-inter-actions [mean distance of 3.667 (2) Å] are present between these dimers. The π-π stacking inter-actions are between aromatic rings with a centroid-centroid distance of 3.884 (2) Å. Moreover, edge-to-face inter-actions are present between eth-oxy CH groups and aromatic rings with H⋯π distances of 2.81 Å.

Related literature

For transition-metal complexes containing 1,3-diaryltriazenide ligands, see: Moore & Robinson (1986 ▶); Vrieze & Van Koten, (1987 ▶); Horner et al. (2006 ▶). For related structures, see: Melardi et al. (2007 ▶, 2009 ▶); Rofouei et al. (2009 ▶).

Experimental

Crystal data

[Hg(C14H13N4O3)Cl]

M = 521.32

Monoclinic,

a = 13.4829 (5) Å

b = 15.5746 (6) Å

c = 7.7545 (3) Å

β = 107.6355 (6)°

V = 1551.84 (10) Å3

Z = 4

Mo Kα radiation

μ = 10.11 mm−1

T = 120 K

0.44 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.142, T max = 0.618

11603 measured reflections

5612 independent reflections

5130 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.047

S = 0.76

5612 reflections

209 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.87 e Å−3

Δρmin = −0.73 e Å−3

Absolute structure: Flack (1983 ▶), 2739 Friedel pairs

Flack parameter: 0.003 (5)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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/S1600536810027819/pv2293sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027819/pv2293Isup2.hkl

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

[Hg(C14H13N4O3)Cl]	F(000) = 984
Mr = 521.32	Dx = 2.231 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5899 reflections
a = 13.4829 (5) Å	θ = 2.6–32.6°
b = 15.5746 (6) Å	µ = 10.11 mm−1
c = 7.7545 (3) Å	T = 120 K
β = 107.6355 (6)°	Needle, red
V = 1551.84 (10) Å3	0.44 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	5612 independent reflections
Radiation source: fine-focus sealed tube	5130 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→20
Tmin = 0.142, Tmax = 0.618	k = −23→23
11603 measured reflections	l = −11→11

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)] = 0.022	H-atom parameters constrained
wR(F2) = 0.047	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
S = 0.76	(Δ/σ)max = 0.002
5612 reflections	Δρmax = 0.87 e Å−3
209 parameters	Δρmin = −0.73 e Å−3
2 restraints	Absolute structure: Flack (1983), 2739 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.003 (5)

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	0.12017 (2)	0.366861 (6)	0.01531 (2)	0.01598 (3)
Cl1	0.09959 (7)	0.22761 (6)	−0.07489 (13)	0.02390 (18)
O1	0.29846 (19)	0.43726 (16)	0.0064 (3)	0.0186 (5)
O2	−0.3935 (2)	0.61872 (18)	0.3415 (5)	0.0284 (6)
O3	−0.4252 (2)	0.48304 (18)	0.3448 (4)	0.0251 (6)
N1	0.1308 (2)	0.49607 (17)	0.0809 (4)	0.0139 (5)
N2	0.0536 (2)	0.52465 (18)	0.1369 (4)	0.0143 (5)
N3	−0.0072 (2)	0.46291 (18)	0.1493 (4)	0.0135 (5)
N4	−0.3717 (2)	0.5440 (2)	0.3237 (4)	0.0178 (6)
C1	0.1976 (2)	0.5559 (2)	0.0397 (4)	0.0141 (6)
C2	0.2875 (3)	0.5247 (2)	0.0013 (4)	0.0158 (6)
C3	0.3560 (3)	0.5818 (2)	−0.0381 (5)	0.0207 (7)
H3	0.4169	0.5612	−0.0620	0.025*
C4	0.3359 (3)	0.6695 (3)	−0.0427 (5)	0.0240 (8)
H4	0.3840	0.7086	−0.0675	0.029*
C5	0.2464 (3)	0.7004 (2)	−0.0112 (5)	0.0240 (7)
H5	0.2326	0.7604	−0.0169	0.029*
C6	0.1767 (3)	0.6436 (2)	0.0287 (5)	0.0177 (6)
H6	0.1149	0.6646	0.0484	0.021*
C7	−0.0947 (2)	0.4891 (2)	0.1988 (4)	0.0126 (6)
C8	−0.1560 (3)	0.4226 (2)	0.2309 (5)	0.0162 (6)
H8	−0.1348	0.3647	0.2252	0.019*
C9	−0.2472 (3)	0.4396 (2)	0.2710 (5)	0.0169 (6)
H9	−0.2888	0.3943	0.2931	0.020*
C10	−0.2762 (3)	0.5245 (2)	0.2780 (5)	0.0158 (6)
C11	−0.2170 (3)	0.5921 (2)	0.2465 (5)	0.0155 (6)
H11	−0.2385	0.6498	0.2531	0.019*
C12	−0.1261 (3)	0.5744 (2)	0.2052 (5)	0.0155 (6)
H12	−0.0853	0.6200	0.1813	0.019*
C13	0.3904 (3)	0.4016 (3)	−0.0273 (5)	0.0206 (7)
H13A	0.4541	0.4228	0.0641	0.025*
H13B	0.3930	0.4188	−0.1487	0.025*
C14	0.3835 (3)	0.3054 (2)	−0.0161 (6)	0.0251 (8)
H14A	0.4450	0.2792	−0.0368	0.038*
H14B	0.3207	0.2851	−0.1083	0.038*
H14C	0.3802	0.2891	0.1042	0.038*

	U11	U22	U33	U12	U13	U23
Hg1	0.01404 (5)	0.01342 (4)	0.02179 (5)	0.00069 (9)	0.00741 (3)	−0.00111 (10)
Cl1	0.0207 (4)	0.0148 (4)	0.0376 (5)	0.0004 (3)	0.0109 (4)	−0.0046 (3)
O1	0.0137 (11)	0.0211 (12)	0.0250 (13)	0.0020 (9)	0.0117 (10)	−0.0003 (10)
O2	0.0230 (14)	0.0235 (14)	0.0441 (18)	0.0042 (11)	0.0182 (13)	0.0018 (12)
O3	0.0175 (13)	0.0306 (15)	0.0307 (15)	−0.0056 (11)	0.0127 (12)	−0.0014 (12)
N1	0.0124 (12)	0.0148 (12)	0.0164 (12)	−0.0001 (10)	0.0070 (11)	−0.0015 (10)
N2	0.0123 (12)	0.0168 (13)	0.0144 (13)	−0.0011 (10)	0.0048 (10)	0.0009 (10)
N3	0.0111 (12)	0.0162 (13)	0.0133 (12)	0.0012 (10)	0.0040 (10)	0.0011 (10)
N4	0.0134 (13)	0.0239 (15)	0.0179 (14)	−0.0031 (11)	0.0074 (11)	−0.0009 (11)
C1	0.0115 (14)	0.0188 (15)	0.0127 (14)	−0.0012 (11)	0.0048 (11)	−0.0004 (12)
C2	0.0161 (15)	0.0196 (16)	0.0132 (14)	0.0017 (12)	0.0067 (12)	0.0004 (12)
C3	0.0151 (15)	0.0282 (19)	0.0209 (17)	−0.0013 (13)	0.0088 (13)	−0.0001 (14)
C4	0.0261 (19)	0.0242 (18)	0.0256 (18)	−0.0077 (15)	0.0134 (16)	0.0024 (15)
C5	0.0248 (19)	0.0191 (17)	0.0308 (19)	−0.0043 (14)	0.0123 (16)	0.0012 (15)
C6	0.0188 (16)	0.0169 (15)	0.0203 (16)	0.0005 (12)	0.0100 (13)	−0.0003 (12)
C7	0.0103 (13)	0.0176 (15)	0.0103 (13)	0.0016 (11)	0.0037 (11)	0.0007 (11)
C8	0.0168 (15)	0.0148 (14)	0.0180 (15)	−0.0013 (12)	0.0067 (12)	−0.0005 (12)
C9	0.0163 (15)	0.0197 (16)	0.0157 (15)	−0.0036 (12)	0.0065 (12)	−0.0010 (12)
C10	0.0138 (15)	0.0221 (16)	0.0135 (14)	−0.0028 (12)	0.0070 (13)	−0.0010 (12)
C11	0.0129 (14)	0.0161 (15)	0.0181 (15)	0.0012 (12)	0.0055 (12)	−0.0014 (12)
C12	0.0142 (15)	0.0144 (14)	0.0180 (15)	−0.0023 (11)	0.0053 (12)	0.0004 (12)
C13	0.0144 (15)	0.0272 (18)	0.0211 (16)	0.0060 (14)	0.0069 (13)	−0.0027 (15)
C14	0.0222 (18)	0.0262 (19)	0.0289 (19)	0.0072 (15)	0.0107 (16)	−0.0008 (15)

Hg1—N1	2.070 (3)	C5—C6	1.392 (5)
Hg1—Cl1	2.2699 (9)	C5—H5	0.9500
Hg1—O1	2.662 (2)	C6—H6	0.9500
Hg1—N3	2.711 (3)	C7—C8	1.394 (4)
O1—C2	1.370 (4)	C7—C12	1.401 (5)
O1—C13	1.453 (4)	C8—C9	1.382 (5)
O2—N4	1.218 (4)	C8—H8	0.9500
O3—N4	1.233 (4)	C9—C10	1.385 (5)
N1—N2	1.320 (4)	C9—H9	0.9500
N1—C1	1.399 (4)	C10—C11	1.387 (5)
N2—N3	1.286 (4)	C11—C12	1.385 (5)
N3—C7	1.406 (4)	C11—H11	0.9500
N4—C10	1.467 (4)	C12—H12	0.9500
C1—C6	1.392 (4)	C13—C14	1.505 (6)
C1—C2	1.419 (4)	C13—H13A	0.9900
C2—C3	1.382 (5)	C13—H13B	0.9900
C3—C4	1.390 (6)	C14—H14A	0.9800
C3—H3	0.9500	C14—H14B	0.9800
C4—C5	1.389 (6)	C14—H14C	0.9800
C4—H4	0.9500
N1—Hg1—Cl1	175.95 (8)	C1—C6—C5	120.0 (3)
N1—Hg1—O1	67.07 (9)	C1—C6—H6	120.0
Cl1—Hg1—O1	114.37 (6)	C5—C6—H6	120.0
N1—Hg1—N3	51.23 (10)	C8—C7—C12	119.8 (3)
Cl1—Hg1—N3	127.80 (6)	C8—C7—N3	115.2 (3)
O1—Hg1—N3	117.69 (8)	C12—C7—N3	124.9 (3)
C2—O1—C13	117.8 (3)	C9—C8—C7	120.9 (3)
C2—O1—Hg1	108.66 (19)	C9—C8—H8	119.5
C13—O1—Hg1	132.3 (2)	C7—C8—H8	119.5
N2—N1—C1	118.5 (3)	C8—C9—C10	118.3 (3)
N2—N1—Hg1	114.0 (2)	C8—C9—H9	120.9
C1—N1—Hg1	126.3 (2)	C10—C9—H9	120.9
N3—N2—N1	110.9 (3)	C9—C10—C11	122.2 (3)
N2—N3—C7	114.2 (3)	C9—C10—N4	119.1 (3)
N2—N3—Hg1	83.78 (18)	C11—C10—N4	118.7 (3)
C7—N3—Hg1	161.0 (2)	C12—C11—C10	119.1 (3)
O2—N4—O3	123.4 (3)	C12—C11—H11	120.4
O2—N4—C10	119.0 (3)	C10—C11—H11	120.4
O3—N4—C10	117.6 (3)	C11—C12—C7	119.7 (3)
C6—C1—N1	122.4 (3)	C11—C12—H12	120.2
C6—C1—C2	119.5 (3)	C7—C12—H12	120.2
N1—C1—C2	118.1 (3)	O1—C13—C14	107.4 (3)
O1—C2—C3	124.9 (3)	O1—C13—H13A	110.2
O1—C2—C1	115.2 (3)	C14—C13—H13A	110.2
C3—C2—C1	119.8 (3)	O1—C13—H13B	110.2
C2—C3—C4	120.0 (3)	C14—C13—H13B	110.2
C2—C3—H3	120.0	H13A—C13—H13B	108.5
C4—C3—H3	120.0	C13—C14—H14A	109.5
C5—C4—C3	120.7 (3)	C13—C14—H14B	109.5
C5—C4—H4	119.7	H14A—C14—H14B	109.5
C3—C4—H4	119.7	C13—C14—H14C	109.5
C4—C5—C6	119.9 (4)	H14A—C14—H14C	109.5
C4—C5—H5	120.0	H14B—C14—H14C	109.5
C6—C5—H5	120.0
N1—Hg1—O1—C2	−16.5 (2)	N1—C1—C2—O1	0.9 (4)
Cl1—Hg1—O1—C2	159.32 (18)	C6—C1—C2—C3	3.1 (5)
N3—Hg1—O1—C2	−24.7 (2)	N1—C1—C2—C3	−179.3 (3)
N1—Hg1—O1—C13	176.7 (3)	O1—C2—C3—C4	178.8 (3)
Cl1—Hg1—O1—C13	−7.4 (3)	C1—C2—C3—C4	−1.0 (5)
N3—Hg1—O1—C13	168.5 (3)	C2—C3—C4—C5	−1.2 (5)
O1—Hg1—N1—N2	−173.2 (2)	C3—C4—C5—C6	1.2 (6)
N3—Hg1—N1—N2	−2.54 (18)	N1—C1—C6—C5	179.4 (3)
O1—Hg1—N1—C1	19.7 (2)	C2—C1—C6—C5	−3.1 (5)
N3—Hg1—N1—C1	−169.6 (3)	C4—C5—C6—C1	0.9 (6)
C1—N1—N2—N3	172.7 (3)	N2—N3—C7—C8	−173.8 (3)
Hg1—N1—N2—N3	4.5 (3)	N2—N3—C7—C12	10.7 (4)
N1—N2—N3—C7	−176.7 (3)	C12—C7—C8—C9	−0.7 (5)
N1—N2—N3—Hg1	−3.1 (2)	N3—C7—C8—C9	−176.5 (3)
N1—Hg1—N3—N2	2.39 (17)	C7—C8—C9—C10	0.1 (5)
Cl1—Hg1—N3—N2	−172.60 (15)	C8—C9—C10—C11	0.0 (5)
O1—Hg1—N3—N2	12.1 (2)	C8—C9—C10—N4	−178.9 (3)
N1—Hg1—N3—C7	164.2 (7)	O2—N4—C10—C9	175.2 (3)
Cl1—Hg1—N3—C7	−10.8 (7)	O3—N4—C10—C9	−3.7 (5)
O1—Hg1—N3—C7	173.8 (6)	O2—N4—C10—C11	−3.6 (5)
N2—N1—C1—C6	−10.1 (5)	O3—N4—C10—C11	177.4 (3)
Hg1—N1—C1—C6	156.5 (3)	C9—C10—C11—C12	0.5 (5)
N2—N1—C1—C2	172.4 (3)	N4—C10—C11—C12	179.3 (3)
Hg1—N1—C1—C2	−21.0 (4)	C10—C11—C12—C7	−1.0 (5)
C13—O1—C2—C3	1.7 (5)	C8—C7—C12—C11	1.1 (5)
Hg1—O1—C2—C3	−167.2 (3)	N3—C7—C12—C11	176.5 (3)
C13—O1—C2—C1	−178.5 (3)	C2—O1—C13—C14	−179.4 (3)
Hg1—O1—C2—C1	12.6 (3)	Hg1—O1—C13—C14	−13.6 (4)
C6—C1—C2—O1	−176.7 (3)

Cg2 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.95	2.54	3.489 (5)	174
C5—H5···O2ii	0.95	2.55	3.390 (5)	147
C9—H9···Cl1iii	0.95	2.80	3.738 (4)	169
C13—H13A···O3iv	0.99	2.47	3.431 (5)	162
C13—H13B···Cg2v	0.99	2.81	3.570 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.95	2.54	3.489 (5)	174
C5—H5⋯O2ii	0.95	2.55	3.390 (5)	147
C9—H9⋯Cl1iii	0.95	2.80	3.738 (4)	169
C13—H13A⋯O3iv	0.99	2.47	3.431 (5)	162
C13—H13B⋯Cg2v	0.99	2.81	3.570 (4)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .