Chlorido[1-(2-eth­oxy­phen­yl)3-(4-nitro­phen­yl)triazenido]mercury(II)

Melardi, M.R.; Roohi, Z.; Heidari, N.; Rofouei, M.K.

doi:10.1107/S1600536810027819

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m975

https://doi.org/10.1107/S1600536810027819

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Chlorido[1-(2-ethoxyphenyl)3-(4-nitrophenyl)triazenido]mercury(II)

Mohammad Reza Melardi,^a ^* Zeynab Roohi,^a Nazanin Heidari ^a and Mohammad Kazem Rofouei ^b

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, and ^bFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran
^*Correspondence e-mail: m.melardi@kiau.ac.ir

(Received 6 June 2010; accepted 13 July 2010; online 21 July 2010)

In the title compound, [Hg(C₁₄H₁₃N₄O₃)Cl], the Hg^II atom is four-coordinated by one O atom and two N atoms from a tridentate 1-(2-ethoxyphenyl)-3-(4-nitrophenyl)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 interactions. In addition, weak Hg–μ⁶-arene π-interactions [mean distance of 3.667 (2) Å] are present between these dimers. The π–π stacking interactions are between aromatic rings with a centroid–centroid distance of 3.884 (2) Å. Moreover, edge-to-face interactions are present between ethoxy 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_r = 521.32
Monoclinic, C c
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[F² > 2σ(F²)] = 0.022
wR(F²) = 0.047
S = 0.76
5612 reflections
209 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.73 e Å⁻³
Absolute structure: Flack (1983 ), 2739 Friedel pairs
Flack parameter: 0.003 (5)

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⋯O3^iv	0.99	2.47	3.431 (5)	162
C13—H13B⋯Cg2^v	0.99	2.81	3.570 (4)	134
Symmetry codes: (i) $[x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x+1, y, z; (v) $[x, -y+1, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027819/pv2293sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027819/pv2293Isup2.hkl

checkCIF report

Comment top

Triazene compounds characterized by having a diazoamino group (–N═NN–) commonly adopt a trans configuration in the ground state. The study of transition-metal complexes containing 1,3-diaryltriaznide ligands has greatly increased in the past few years because of the versatility of their coordination forms, yielding a variety of coordination compounds with large structural diversity (Moore & Robinson, 1986; Vrieze & Van Koten, 1987; Horner et al.., 2006). The crystal structures of a few complexes related to the title compound have been reported recently (Melardi et al., 2007; Rofouei et al., 2009).

In the title complex (Fig. 1), the [1-(2-ethoxyphenyl)3-(4-nitrophenyl)]triazenide ion is coordinated to the central atom Hg(II) through two N atoms [Hg1—N1 = 2.070 (3) Å and Hg1—N3 = 2.711 (3) Å] and one O atom [Hg1—O1 = 2.662 (2) Å]. In addition, a Cl^- ion is coordinated to Hg(II) atom with the bond distance Hg1—Cl1 = 2.269 (9) Å. These bond distances agree very well with the corresponding distances reported in related structures (Melardi et al., 2007; Rofouei et al., 2009). The atoms of the ligand and lie in a plane (maximum deviation from coplanarity being 0.115 (4)Å for O2 while Cl1 and Hg1 lie 1.402 (3) and 0.606 (2)Å, respecively, out of this plane. The molecules of the title complex are linked to form pairs through non-classical C—H···O and C—H···Cl hydrogen bond, as well as π–π and C—H···π stacking interactions.

There are π–π stacking interactions present between aromatic rings with centroid-centroid distance of 3.884 (2) Å for Cg1···Cg1 (Cg1 = C7—C12, x, 1 - y, z-1/2), and also edge-to-face interactions are present between CH group of ethoxy with aromatic rings with H···π distance of 2.81 Å for C13—H13B···Cg2 (Cg2 = C1—C6 x, 1 - y, z-1/2). In addition, weak Hg-µ⁶-arene π-interactions (mean distance 3.667 (2) Å) are present between these dimers. The secondary Hg-µ⁶-arene π-interactions involve carbon atoms of the C1—C6 phenyl rings (Table 1, Fig. 2). The weak non-covalent interactions seem to play important role in the crystal packing and the formation of a desired framework. The unit cell packing of the title compound is shown in Fig. 3.

Related literature top

For transition-metal complexes containing 1,3-diaryltriaznide 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 top

A methanol solution of 1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazene (0.286 g, 1 mmol) was added to a solution of mercury(II) chloride (0.270 g, 1 mmol). After mixing for 30 minutes at room temperature, solution of sodium acetate in water was added to adjust the pH at 6–6.2. After 2 h, a red solid was readily precipitated out. It was filtered off, washed with methanol and dried in vacuum. The orange crude material was dissolved in 10 ml of dichloromethane (CH₂Cl₂), and placed in a freezer without covering. After two weeks beautiful orange and air-stable crystals of the title complex were obtained by slow evaporation of the solvent; m.p. 460–462 K.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, with ellipsoids drawn at 50% probability level.
	Fig. 2. π–π, C—H···π and weak Hg-µ⁶-arene stacking interactions between two [Hg(C₁₄H₁₃N₄O₃)Cl] moieties.
	Fig. 3. The unit cell packing diagram of the title compound along the c axis.

Chlorido[1-(2-ethoxyphenyl)3-(4-nitrophenyl)triazenido]mercury(II) top

Crystal data top

[Hg(C₁₄H₁₃N₄O₃)Cl]	F(000) = 984
M_r = 521.32	D_x = 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

Data collection top

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

Refinement top

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(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.76	(Δ/σ)_max = 0.002
5612 reflections	Δρ_max = 0.87 e Å⁻³
209 parameters	Δρ_min = −0.73 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2739 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.003 (5)

Crystal data top

[Hg(C₁₄H₁₃N₄O₃)Cl]	V = 1551.84 (10) Å³
M_r = 521.32	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 13.4829 (5) Å	µ = 10.11 mm⁻¹
b = 15.5746 (6) Å	T = 120 K
c = 7.7545 (3) Å	0.44 × 0.10 × 0.08 mm
β = 107.6355 (6)°

Data collection top

Bruker APEXII CCD diffractometer	5612 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5130 reflections with I > 2σ(I)
T_min = 0.142, T_max = 0.618	R_int = 0.031
11603 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.047	Δρ_max = 0.87 e Å⁻³
S = 0.76	Δρ_min = −0.73 e Å⁻³
5612 reflections	Absolute structure: Flack (1983), 2739 Friedel pairs
209 parameters	Absolute structure parameter: 0.003 (5)
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.99	2.47	3.431 (5)	162
C13—H13B···Cg2^v	0.99	2.81	3.570 (4)	134

Symmetry codes: (i) x+1, −y+1, z−1/2; (ii) x+1/2, −y+3/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) x+1, y, z; (v) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Hg(C₁₄H₁₃N₄O₃)Cl]
M_r	521.32
Crystal system, space group	Monoclinic, Cc
Temperature (K)	120
a, b, c (Å)	13.4829 (5), 15.5746 (6), 7.7545 (3)
β (°)	107.6355 (6)
V (Å³)	1551.84 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.11
Crystal size (mm)	0.44 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.142, 0.618
No. of measured, independent and observed [I > 2σ(I)] reflections	11603, 5612, 5130
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.761

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.047, 0.76
No. of reflections	5612
No. of parameters	209
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.73
Absolute structure	Flack (1983), 2739 Friedel pairs
Absolute structure parameter	0.003 (5)

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.99	2.47	3.431 (5)	162
C13—H13B···Cg2^v	0.99	2.81	3.570 (4)	134

Symmetry codes: (i) x+1, −y+1, z−1/2; (ii) x+1/2, −y+3/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) x+1, y, z; (v) x, −y+1, z−1/2.

References

Bruker (2001). SAINT-Plus. and SADABS Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Melardi, M. R., Salemi, Y., Razi Kazemi, S. & Rofouei, M. K. (2009). Acta Cryst. E65, m302. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moore, D. S. & Robinson, S. D. (1986). Adv. Inorg. Chem. Radiochem. 30, 1–68. CrossRef CAS Web of Science Google Scholar
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Volume 66| Part 8| August 2010| Page m975

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