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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): m302.
Published online 2009 February 21. doi:  10.1107/S160053680900539X
PMCID: PMC2968604

[1,3-Bis(2-ethoxy­phen­yl)triazenido]chloridomercury(II)

Abstract

In the title compound, [Hg(C16H18N3O2)Cl], the HgII atom is four-coordinated in a tetra­hedral geometry by two N atoms from the 1,3-chelating and one O atom of a 1,3-bis­(2-ethoxy­phen­yl)triazenido ligand and one terminal chloride ion. The dihedral angle between the aromatic rings is 1.72 (14)°. In the crystal C—H(...)π stacking inter­actions occur.

Related literature

For related structures, see: Rofouei et al. 2008 [triangle]; Melardi et al. 2007 [triangle].

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Object name is e-65-0m302-scheme1.jpg

Experimental

Crystal data

  • [Hg(C16H18N3O2)Cl]
  • M r = 520.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m302-efi1.jpg
  • a = 10.1600 (5) Å
  • b = 7.3802 (4) Å
  • c = 22.5655 (11) Å
  • β = 97.817 (1)°
  • V = 1676.30 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 9.35 mm−1
  • T = 100 K
  • 0.15 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (APEX2; Bruker, 2005 [triangle]) T min = 0.280, T max = 0.479
  • 19713 measured reflections
  • 4451 independent reflections
  • 4009 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.049
  • S = 1.01
  • 4451 reflections
  • 210 parameters
  • H-atom parameters constrained
  • Δρmax = 0.98 e Å−3
  • Δρmin = −1.19 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900539X/pv2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900539X/pv2138Isup2.hkl

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

supplementary crystallographic information

Comment

Recently we have reported the synthesis and crystal structure of [1,3-bis(2-methoxyphenyl)triazene with HgII as ML2 structure [Rofouei et al., 2008] and [1,3-bis(2-methoxybenzene)triazene with HgII as ML structure [Melardi et al., 2007]. In this article we report the synthesis and crystal structure of the title compound, (I).

In the title compound, the HgII atom is four-coordinated in a tetrahedral configuration by two N atoms from the chelating (1,3) and one O atom of ethoxyphenyl triazenido ligand and one terminal Cl atom leading to an asymmetric molecule (Fig. 1). There are interesting C—H···π stacking interactions between CH groups and aromatic phenyl rings with C—H···π distances of 2.869 Å for C3—H3A···Cg1 (5/2 - x, 1/2 + y, 1/2 - z) and 2.681 Å for C15—H15B···Cg1 (2 - x, 1 - y, -z) (Cg1 is centroid of C1—C6 ring) as presented in Fig. 2. The unit cell packing of the title compound showing stacking of molecules is presented at Fig. 3.

Experimental

A solution of [1,3-bis(2-ethoxyphenyl)triazene] (1 mmol, 0.285 g) in acetonitril (10 ml) and triethylamin (0.3 ml) was added to a solution of HgCl2 (1 mmol, 0.271 g) in methanol (10 ml) yielded the title compound. The suitable crystals for X-ray analysis were obtained from a solution of ethyl acetate after one week. m.p. = 449-451 K.

Refinement

All hydrogen atoms were included in the refinement at calculated positions in isotropic approximation in riding mode with distances C—H = 0.95, 0.99 and 0.98 Å for aryl, methylene and methyl groups, respectively, and Uiso(H) parameters equal to 1.2Ueq(C) for methylene and aryl groups and equal to 1.5Ueq(C) for methyl groups.

Figures

Fig. 1.
Molecular structure of the title complex. Thermal ellipsoids are drawn at 50% probability level.
Fig. 2.
C—H···π Stacking interactions between CH groups and aromatic phenyl rings centroid.
Fig. 3.
Unit cell packing diagram of the title complex.

Crystal data

[Hg(C16H18N3O2)Cl]F(000) = 992
Mr = 520.37Dx = 2.062 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8520 reflections
a = 10.1600 (5) Åθ = 3–29°
b = 7.3802 (4) ŵ = 9.35 mm1
c = 22.5655 (11) ÅT = 100 K
β = 97.817 (1)°Prism, colorless
V = 1676.30 (15) Å30.15 × 0.12 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer4451 independent reflections
Radiation source: fine-focus sealed tube4009 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (APEX2; Bruker, 2005)h = −13→13
Tmin = 0.280, Tmax = 0.479k = −10→10
19713 measured reflectionsl = −30→30

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.02P)2 + 2P] where P = (Fo2 + 2Fc2)/3
4451 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.98 e Å3
0 restraintsΔρmin = −1.19 e Å3

Special details

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)

xyzUiso*/Ueq
Hg10.849438 (10)0.312052 (15)0.054958 (5)0.01838 (4)
Cl10.65126 (8)0.35249 (12)0.09032 (4)0.03193 (18)
O11.0251 (2)0.5538 (3)0.20153 (9)0.0187 (4)
O20.82363 (19)0.1411 (3)−0.05286 (9)0.0174 (4)
N11.0926 (2)0.4172 (3)0.10284 (10)0.0159 (4)
N21.1288 (2)0.3584 (3)0.05434 (11)0.0160 (5)
N31.0261 (2)0.2874 (3)0.01919 (11)0.0158 (5)
C11.1957 (3)0.4946 (4)0.14348 (12)0.0154 (5)
C21.1558 (3)0.5710 (4)0.19570 (12)0.0162 (5)
C31.2500 (3)0.6550 (4)0.23737 (13)0.0195 (6)
H3A1.22360.70970.27200.023*
C41.3828 (3)0.6591 (4)0.22844 (13)0.0198 (6)
H4A1.44640.71740.25690.024*
C51.4232 (3)0.5785 (4)0.17820 (13)0.0197 (6)
H5A1.51430.57900.17280.024*
C61.3297 (3)0.4974 (4)0.13598 (13)0.0175 (5)
H6A1.35720.44320.10150.021*
C70.9817 (3)0.6273 (4)0.25429 (14)0.0237 (6)
H7A0.99540.76010.25590.028*
H7B1.03240.57270.29050.028*
C80.8362 (3)0.5833 (5)0.25128 (16)0.0304 (7)
H8A0.80210.63400.28640.046*
H8B0.82420.45150.25070.046*
H8C0.78740.63590.21480.046*
C91.0519 (3)0.2108 (4)−0.03482 (12)0.0153 (5)
C100.9451 (3)0.1305 (4)−0.07242 (12)0.0148 (5)
C110.9671 (3)0.0489 (4)−0.12541 (12)0.0183 (5)
H11A0.8950−0.0038−0.15080.022*
C121.0944 (3)0.0436 (4)−0.14161 (13)0.0204 (6)
H12A1.1091−0.0147−0.17770.024*
C131.1995 (3)0.1227 (4)−0.10547 (13)0.0210 (6)
H13A1.28600.1197−0.11700.025*
C141.1789 (3)0.2072 (4)−0.05198 (13)0.0183 (6)
H14A1.25120.2621−0.02740.022*
C150.7136 (3)0.0536 (4)−0.08871 (13)0.0190 (5)
H15A0.7319−0.0773−0.09250.023*
H15B0.69930.1072−0.12930.023*
C160.5924 (3)0.0808 (5)−0.05819 (15)0.0258 (6)
H16A0.51880.0086−0.07850.039*
H16B0.56770.2092−0.05980.039*
H16C0.61170.0423−0.01630.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.01754 (6)0.02133 (6)0.01728 (6)0.00076 (4)0.00604 (4)−0.00146 (4)
Cl10.0241 (4)0.0361 (4)0.0390 (5)−0.0002 (3)0.0165 (3)−0.0071 (3)
O10.0217 (10)0.0216 (10)0.0140 (9)−0.0016 (8)0.0065 (8)−0.0038 (8)
O20.0142 (9)0.0238 (10)0.0144 (9)−0.0025 (7)0.0026 (8)−0.0018 (8)
N10.0206 (11)0.0148 (11)0.0119 (10)0.0023 (9)0.0014 (9)−0.0006 (9)
N20.0193 (11)0.0152 (11)0.0130 (11)0.0024 (9)0.0007 (9)0.0007 (8)
N30.0156 (11)0.0189 (12)0.0127 (11)−0.0012 (9)0.0016 (9)0.0002 (9)
C10.0193 (13)0.0121 (12)0.0142 (12)0.0003 (10)0.0000 (10)0.0001 (10)
C20.0207 (13)0.0132 (12)0.0146 (12)0.0013 (10)0.0020 (10)0.0011 (10)
C30.0268 (15)0.0160 (14)0.0150 (13)0.0007 (11)0.0010 (11)−0.0007 (10)
C40.0259 (14)0.0145 (13)0.0171 (13)−0.0006 (11)−0.0046 (11)0.0019 (10)
C50.0171 (13)0.0196 (14)0.0212 (14)0.0009 (11)−0.0017 (11)0.0021 (11)
C60.0208 (13)0.0164 (13)0.0151 (13)0.0027 (10)0.0017 (11)0.0013 (10)
C70.0329 (17)0.0215 (14)0.0182 (14)−0.0011 (12)0.0095 (13)−0.0021 (11)
C80.0306 (17)0.0317 (18)0.0326 (18)−0.0023 (14)0.0175 (14)−0.0018 (14)
C90.0179 (13)0.0167 (13)0.0115 (12)0.0016 (10)0.0023 (10)0.0017 (10)
C100.0160 (12)0.0141 (12)0.0146 (12)−0.0005 (10)0.0028 (10)0.0031 (10)
C110.0224 (13)0.0196 (13)0.0128 (12)−0.0014 (11)0.0016 (10)−0.0001 (11)
C120.0226 (14)0.0243 (15)0.0150 (13)0.0047 (11)0.0050 (11)0.0011 (11)
C130.0182 (13)0.0262 (15)0.0191 (14)0.0052 (11)0.0043 (11)0.0004 (12)
C140.0161 (12)0.0239 (15)0.0148 (13)−0.0010 (10)0.0016 (10)0.0004 (11)
C150.0166 (12)0.0210 (14)0.0186 (13)−0.0030 (11)−0.0006 (10)0.0012 (11)
C160.0169 (13)0.0344 (17)0.0268 (16)−0.0021 (12)0.0053 (12)0.0041 (13)

Geometric parameters (Å, °)

Hg1—N32.074 (2)C7—C81.507 (5)
Hg1—Cl12.2840 (8)C7—H7A0.9900
Hg1—N12.674 (2)C7—H7B0.9900
Hg1—O22.721 (2)C8—H8A0.9800
O1—C21.358 (3)C8—H8B0.9800
O1—C71.431 (3)C8—H8C0.9800
O2—C101.368 (3)C9—C141.397 (4)
O2—C151.441 (3)C9—C101.413 (4)
N1—N21.277 (3)C10—C111.384 (4)
N1—C11.415 (3)C11—C121.391 (4)
N2—N31.329 (3)C11—H11A0.9500
N3—C91.400 (4)C12—C131.382 (4)
C1—C61.395 (4)C12—H12A0.9500
C1—C21.415 (4)C13—C141.399 (4)
C2—C31.393 (4)C13—H13A0.9500
C3—C41.391 (4)C14—H14A0.9500
C3—H3A0.9500C15—C161.503 (4)
C4—C51.391 (4)C15—H15A0.9900
C4—H4A0.9500C15—H15B0.9900
C5—C61.386 (4)C16—H16A0.9800
C5—H5A0.9500C16—H16B0.9800
C6—H6A0.9500C16—H16C0.9800
N3—Hg1—Cl1176.60 (7)C8—C7—H7B110.3
N3—Hg1—N151.80 (8)H7A—C7—H7B108.6
Cl1—Hg1—N1129.12 (5)C7—C8—H8A109.5
N3—Hg1—O266.09 (8)C7—C8—H8B109.5
Cl1—Hg1—O2112.99 (5)H8A—C8—H8B109.5
N1—Hg1—O2117.86 (6)C7—C8—H8C109.5
Hg1—O2—C10109.48 (8)H8A—C8—H8C109.5
Hg1—O2—C15133.07 (16)H8B—C8—H8C109.5
C2—O1—C7117.4 (2)C14—C9—N3122.6 (3)
C10—O2—C15117.3 (2)C14—C9—C10119.2 (3)
N2—N1—C1114.7 (2)N3—C9—C10118.2 (2)
N2—N1—Hg185.01 (16)O2—C10—C11124.2 (2)
C1—N1—Hg1160.18 (18)O2—C10—C9115.8 (2)
N1—N2—N3110.6 (2)C11—C10—C9120.0 (3)
N2—N3—C9117.0 (2)C10—C11—C12120.3 (3)
N2—N3—Hg1112.58 (18)C10—C11—H11A119.9
C9—N3—Hg1130.44 (19)C12—C11—H11A119.9
C6—C1—C2119.4 (3)C13—C12—C11120.3 (3)
C6—C1—N1125.2 (3)C13—C12—H12A119.9
C2—C1—N1115.5 (2)C11—C12—H12A119.9
O1—C2—C3124.6 (3)C12—C13—C14120.2 (3)
O1—C2—C1116.0 (2)C12—C13—H13A119.9
C3—C2—C1119.4 (3)C14—C13—H13A119.9
C4—C3—C2120.2 (3)C9—C14—C13120.0 (3)
C4—C3—H3A119.9C9—C14—H14A120.0
C2—C3—H3A119.9C13—C14—H14A120.0
C3—C4—C5120.6 (3)O2—C15—C16107.7 (2)
C3—C4—H4A119.7O2—C15—H15A110.2
C5—C4—H4A119.7C16—C15—H15A110.2
C6—C5—C4119.6 (3)O2—C15—H15B110.2
C6—C5—H5A120.2C16—C15—H15B110.2
C4—C5—H5A120.2H15A—C15—H15B108.5
C5—C6—C1120.8 (3)C15—C16—H16A109.5
C5—C6—H6A119.6C15—C16—H16B109.5
C1—C6—H6A119.6H16A—C16—H16B109.5
O1—C7—C8107.0 (3)C15—C16—H16C109.5
O1—C7—H7A110.3H16A—C16—H16C109.5
C8—C7—H7A110.3H16B—C16—H16C109.5
O1—C7—H7B110.3
N3—Hg1—O2—C100.40 (16)N1—C1—C2—C3−178.1 (2)
Cl1—Hg1—O2—C10176.84 (15)O1—C2—C3—C4177.3 (3)
N1—Hg1—O2—C10−1.31 (18)C1—C2—C3—C4−1.8 (4)
N3—Hg1—O2—C15175.4 (2)C2—C3—C4—C5−0.5 (4)
Cl1—Hg1—O2—C15−8.2 (2)C3—C4—C5—C61.6 (4)
N1—Hg1—O2—C15173.7 (2)C4—C5—C6—C1−0.5 (4)
N3—Hg1—N1—N21.55 (15)C2—C1—C6—C5−1.8 (4)
Cl1—Hg1—N1—N2−174.26 (12)N1—C1—C6—C5179.3 (3)
O2—Hg1—N1—N23.54 (17)C2—O1—C7—C8−177.5 (2)
N3—Hg1—N1—C1177.1 (6)N2—N3—C9—C140.1 (4)
Cl1—Hg1—N1—C11.3 (6)Hg1—N3—C9—C14179.6 (2)
O2—Hg1—N1—C1179.1 (5)N2—N3—C9—C10178.6 (2)
C1—N1—N2—N3179.6 (2)Hg1—N3—C9—C10−2.0 (4)
Hg1—N1—N2—N3−2.03 (19)C15—O2—C10—C113.1 (4)
N1—N2—N3—C9−177.6 (2)C15—O2—C10—C9−177.3 (2)
N1—N2—N3—Hg12.8 (3)C14—C9—C10—O2−179.4 (2)
N1—Hg1—N3—N2−1.61 (15)N3—C9—C10—O22.1 (4)
N1—Hg1—N3—C9178.9 (3)C14—C9—C10—C110.3 (4)
N2—N1—C1—C6−5.0 (4)N3—C9—C10—C11−178.2 (2)
Hg1—N1—C1—C6179.8 (4)O2—C10—C11—C12−179.6 (3)
N2—N1—C1—C2176.1 (2)C9—C10—C11—C120.7 (4)
Hg1—N1—C1—C20.9 (7)C10—C11—C12—C13−1.2 (4)
C7—O1—C2—C30.0 (4)C11—C12—C13—C140.6 (5)
C7—O1—C2—C1179.1 (2)N3—C9—C14—C13177.6 (3)
C6—C1—C2—O1−176.3 (2)C10—C9—C14—C13−0.9 (4)
N1—C1—C2—O12.7 (4)C12—C13—C14—C90.4 (4)
C6—C1—C2—C32.9 (4)C10—O2—C15—C16179.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···Cg1i0.952.873.598 (3)134
C15—H15B···Cg1ii0.992.683.511 (3)142

Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2138).

References

  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc. Madison, Wisconsin, USA.
  • Melardi, M. R., Rofouei, M. K. & Massomi, J. (2007). Anal. Sci.23, x67–x68.
  • Rofouei, M. K., Melardi, M. R., Barkhi, M. & Khalili Ghaydar, H. R. (2008). Anal. Sci.24, x81–x82.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography