metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis[2-(2-methyl­phenyl­imino)phen­yl]mercury(II)

aSchool of Chemistry, University of Manchester, Sackville Street, Manchester, England
*Correspondence e-mail: k.r.flower@manchester.ac.uk

(Received 19 May 2006; accepted 29 May 2006; online 9 June 2006)

The structure of the cyclo­mercurated 2-phenyl­imino­phenyl title compound, [Hg(C14H12N)2], shows that the mercury coordination is essentially square planar

Comment

The structure of the title compound, (I)[link], is shown in Fig. 1[link]. Organomercurials are often used as transmetallation reagents in the synthesis of organometallic complexes (Roper & Wright, 1977[Roper, W. R. & Wright, L. J. (1977). J. Organomet. Chem. 142, C1-C6.]). Several years ago we reported a synthetic route for the preparation of a range of functionalized 1-mercurio-2-phenyl­imino­phenyls (Flower et al., 2002[Flower, K. R., Howard, V. J., Naguthney, S., Pritchard, R. G., Warren, J. E. & McGown, A. T. (2002). Inorg. Chem. 41, 1907-1912.]) and from the structural data obtained concurred with a previous report of Batsanov (1998[Batsanov, A. S. (1998). J. Chem. Soc. Dalton Trans. pp. 1541-1546.]) that the van der Waals radius of mercury is in the range 2.0–2.2 Å, rather than the often quoted value of 1.55 Å (Bondi, 1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]). Here, and in the following paper (Flower & Pritchard, 2006[Flower, K. R. & Pritchard, R. G. (2006). Acta Cryst. E62, m1469-m1470.]), we report two additional structures of this type of compound. All of the bond lengths and angles in the two structures are as expected. The Hg—N distances in (I)[link] and bis-2-(2-isopropyl­phenyl­imnophen­yl)­mercury, (II), range from 2.787 (10) to 2.850 (10) Å and are comfortably within the sum of the van der Waals radii (3.5–3.7 Å), if the van der Waals radius of Hg is considered to be 2.0–2.2 Å, indicating significant Hg—N inter­actions. This gives rise to an overall distorted square-planar geometry at Hg in both cases. Other examples of square planar HgII complexes are known (Balasubramani et al., 2005[Balasubramani, K., Thomas, P., Bocelli, G. & Cantoni, A. (2005). J. Coord. Chem. 58, 1689-1694.]; Haid et al., 2003[Haid, R., Gutmann, R., Czermak, G., Langes, C., Oberhauser, W, Kopacka, H., Ongania, K.-H. & Bruggeller, P. (2003). Inorg. Chem. Commun. 6, 61-67.]; Cheng et al., 1994[Cheng, Y., Emge, T. J. & Brennan, J. G. (1994). Inorg. Chem. 33, 3711-3714.]).

[Scheme 1]
[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atomic numbering scheme. Displacement ellipsoids are shown at the 30% probability level.

Experimental

Caution: preparation of an organomercurial. Organomercurials are extremely toxic. To Hg(C6H4-2-CHO)2 (1 g, 2.4 mmol) dissolved in ethanol (10 ml) containing p-toluene­sulfonic acid (10 mg, 0.05 mmol) was added 2-methyl­aniline (0.56 g, 6 mmol) and the solution was refluxed for 5 h, during which time white crystals of (I)[link] precipitated. The crystalline material was collected by filtration, washed with water and dried in a desiccator. Yield 0.93 g, 68%. An analytically pure sample was obtained through recrystallization from hot ethanol, and crystals suitable for the diffraction study were grown by dissolving approximately 10 mg of (I)[link] in CH2Cl2 (0.2 ml) in a small vial (1 × 5 cm), layering ethanol (5 ml) on top and leaving the vial to to stand for 24 h. Elemental analysis C28H24HgN2 requires: C 57.56, H 4.11, N 4.76%; found: C 57.79, H 4.22, N 4.91%.

Crystal data
  • [Hg(C14H12N)2]

  • Mr = 589.08

  • Monoclinic, P 21 /c

  • a = 11.9925 (3) Å

  • b = 11.3864 (3) Å

  • c = 16.6542 (5) Å

  • β = 97.6730 (10)°

  • V = 2253.79 (11) Å3

  • Z = 4

  • Dx = 1.736 Mg m−3

  • Mo Kα radiation

  • μ = 6.85 mm−1

  • T = 293 (2) K

  • Plate, yellow

  • 0.2 × 0.15 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.254, Tmax = 0.707

  • 14711 measured reflections

  • 5084 independent reflections

  • 3476 reflections with I > 2σ(I)

  • Rint = 0.086

  • θmax = 27.4°

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.092

  • S = 1.02

  • 5084 reflections

  • 283 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0284P)2 + 5.7069P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 1.54 e Å−3

  • Δρmin = −1.64 e Å−3

  • Extinction correction: SHELXL97

  • Extinction coefficient: 0.00103 (15)

H atoms were positioned geometrically and treated as riding, with C—H = 0.93 and 0.96 Å, and with Uiso(H) values of 1.2 and 1.5 times Ueq(C). The highest residual peak is located 1.03 Å from Hg1 and deepest hole is located 0.92 Å from Hg1..

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-888.]).

Supporting information


Comment top

The stucture of the title compound, (I), is shown below. Organomercurials are often used as transmetallation reagents in the synthesis of organometallic complexes (Roper & Wright 1977). Several years ago we reported a synthetic route for the preparation of a range of functionalized 1-mercurio-2-phenyliminophenyls (Flower et al. 2002) and from the structural data obtained concurred with a previous report of Batsanov et al. (1998) that the van der Waals radius of mercury is in the range 2.0–2.2 Å, rather than the often quoted value of 1.55 Å (Bondi 1964). Here, and in the following paper (Flower & Pritchard 2006), we report two additional structures of this type of compound. All of the bond lengths and angles in the two structures are as expected. The Hg—N distances in (I) and bis-2-(2-isopropylphenylimnophenyl)mercury, (II), range from 2.787 (10)–2.850 (10) Å and are comfortably within the sum of the van der Waals radii (3.5–3.7 Å), if the van der Waals radius of Hg is considered to be 2 − 2.2 Å, indicating significant Hg—N interactions. This gives rise to an overall distorted square-planar geometry at Hg in both cases. Other examples of square planar HgII complexes are known (Balasubramani et al. 2005; Haid et al. 2003; Cheng et al. 1994).

Experimental top

Caution: preparation of an organomercurial. To Hg(C6H4-2-CHO)2 (1 g, 2.4 mmol) dissolved in ethanol (10 ml) containing p-toluene sulfonic acid (10 mg, 0.05 mmol) was added 2-methylaniline (0.56 g, 6 mmol) and the solution was refluxed for 5 h, during which time white crystals of (I) precipitated. The crystalline material was collected by filtration, washed with water and dried in a desiccator. Yield 0.93 g, 68%. An analytically pure sample was obtained through recrystallization from hot ethanol, and crystals suitable for the diffraction study were grown by dissolving approximately 10 mg of (I) in CH2Cl2 (0.2 ml) in a small vial (1 × 5 cm), layering ethanol (5 ml) on top and leaving the vial to to stand for 24 h. Elemental analysis C28H24HgN2 requires: C 57.56, H 4.11, N 4.76%; found: C 57.79, H 4.22, N 4.91%. 1H NMR (CDCl3, 200 MHz): δ 8.50 (s, CH, JHHg = 10.41 Hz), 7.65–7.06 (m, 14H, aryl-H), 6.73 (d, 2H, aryl-H, JHH = 7.07 Hz), 2.15 (s, 3H, CH3). 13C{1H} NMR (CDCl3, 100 MHz): δ 167.5, 164.6, 151.2, 143.9, 139.1, 133.4, 131.9, 131.3, 130.0, 127.3, 126.6, 125.4, 118.4, 18.3.

Refinement top

H atoms were positioned geometrically and treated as riding, with C—H = 0.93 and 0.96 Å, and with Uiso(H) values of 1.2 and 1.5 times Ueq(C). Please check added text. Please specify locations of highest residual density peak and deepest hole.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1]
Fig. 1. The molecules of (I), showing the atomic numbering scheme. Displacement ellipsoids are shown at the 30% probability level.

Fig. 2. Packing diagram of (I), viewed normal to the (010) plane.
(I) top
Crystal data top
[Hg(C14H12N)2]F(000) = 1144
Mr = 589.08Dx = 1.736 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13603 reflections
a = 11.9925 (3) Åθ = 1.0–27.5°
b = 11.3864 (3) ŵ = 6.85 mm1
c = 16.6542 (5) ÅT = 293 K
β = 97.673 (1)°Plate, yellow
V = 2253.79 (11) Å30.2 × 0.15 × 0.05 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
5084 independent reflections
Radiation source: Enraf–Nonius FR5903476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
Detector resolution: 9 pixels mm-1θmax = 27.4°, θmin = 3.2°
CCD rotation images, thick slices scansh = 1515
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1414
Tmin = 0.254, Tmax = 0.707l = 2119
14711 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0284P)2 + 5.7069P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5084 reflectionsΔρmax = 1.54 e Å3
283 parametersΔρmin = 1.64 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00103 (15)
Crystal data top
[Hg(C14H12N)2]V = 2253.79 (11) Å3
Mr = 589.08Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9925 (3) ŵ = 6.85 mm1
b = 11.3864 (3) ÅT = 293 K
c = 16.6542 (5) Å0.2 × 0.15 × 0.05 mm
β = 97.673 (1)°
Data collection top
Nonius KappaCCD
diffractometer
5084 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
3476 reflections with I > 2σ(I)
Tmin = 0.254, Tmax = 0.707Rint = 0.086
14711 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.02Δρmax = 1.54 e Å3
5084 reflectionsΔρmin = 1.64 e Å3
283 parameters
Special details top

Experimental. 1H NMR (CDCl3, 200 MHz): δ 8.50 (s, CH, JHHg = 10.41 Hz), 7.65–7.06 (m, 14H, aryl-H), 6.73 (d, 2H, aryl-H, JHH = 7.07 Hz), 2.15 (s, 3H, CH3). 13C{1H} NMR (CDCl3, 100 MHz): δ 167.5, 164.6, 151.2, 143.9, 139.1, 133.4, 131.9, 131.3, 130.0, 127.3, 126.6, 125.4, 118.4, 18.3.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Hg10.51462 (2)0.41352 (2)0.389990 (15)0.02255 (12)
C10.4516 (6)0.3315 (6)0.4861 (4)0.0235 (16)
C20.3449 (7)0.3543 (6)0.5050 (4)0.0320 (18)
H20.3010.40990.47460.038*
C30.3004 (7)0.2977 (7)0.5676 (5)0.042 (2)
H30.22780.31450.57790.05*
C40.3658 (8)0.2160 (7)0.6143 (5)0.045 (2)
H40.33710.17610.65580.054*
C50.4737 (7)0.1950 (7)0.5985 (4)0.037 (2)
H50.5190.14380.6320.044*
C60.5164 (6)0.2467 (6)0.5351 (4)0.0256 (16)
C70.6273 (7)0.2110 (6)0.5197 (4)0.0285 (18)
H70.66330.15260.55250.034*
C80.7850 (7)0.2068 (6)0.4513 (4)0.0297 (18)
C90.7969 (8)0.0870 (7)0.4347 (4)0.040 (2)
H90.73650.03620.43610.048*
C100.8987 (10)0.0445 (9)0.4162 (5)0.059 (3)
H100.90660.03410.4030.07*
C110.9875 (9)0.1205 (10)0.4176 (5)0.062 (3)
H111.05640.09170.40640.075*
C120.9784 (7)0.2378 (9)0.4351 (5)0.050 (2)
H121.04040.2870.43590.06*
C130.8744 (6)0.2830 (7)0.4517 (4)0.0333 (19)
C140.8630 (7)0.4101 (7)0.4717 (5)0.041 (2)
H14A0.79250.43930.44510.062*
H14B0.92360.45360.45370.062*
H14C0.86550.4190.52920.062*
C150.5770 (6)0.4864 (5)0.2894 (4)0.0203 (15)
C160.6826 (6)0.4634 (6)0.2706 (4)0.0281 (17)
H160.72880.4130.30410.034*
C170.7238 (7)0.5116 (6)0.2042 (4)0.0308 (18)
H170.79550.49260.19290.037*
C180.6569 (6)0.5882 (6)0.1549 (4)0.0285 (17)
H180.68420.62420.11140.034*
C190.5489 (5)0.6109 (5)0.1710 (4)0.0146 (13)
H190.50220.65850.13560.018*
C200.5089 (6)0.5652 (5)0.2377 (4)0.0215 (15)
C210.3909 (6)0.5915 (6)0.2481 (4)0.0231 (15)
H210.35470.65280.21820.028*
C220.2222 (6)0.5675 (6)0.3016 (4)0.0240 (16)
C230.1905 (6)0.6849 (6)0.3109 (4)0.0290 (17)
H230.24380.74430.31150.035*
C240.0817 (7)0.7121 (6)0.3190 (4)0.0346 (19)
H240.06120.78990.3260.041*
C250.0029 (7)0.6249 (7)0.3169 (4)0.0347 (19)
H250.07160.64390.3210.042*
C260.0332 (6)0.5085 (7)0.3087 (4)0.0315 (18)
H260.02110.45010.30850.038*
C270.1438 (6)0.4775 (6)0.3007 (4)0.0249 (16)
C280.1756 (6)0.3514 (6)0.2904 (5)0.0342 (19)
H28A0.18680.33780.23520.051*
H28B0.11640.30140.3040.051*
H28C0.24380.33430.32550.051*
N10.6795 (5)0.2533 (5)0.4645 (3)0.0272 (13)
N20.3364 (5)0.5348 (5)0.2958 (3)0.0230 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.02761 (18)0.02238 (15)0.01747 (16)0.00002 (15)0.00228 (10)0.00166 (12)
C10.025 (4)0.025 (4)0.019 (4)0.007 (3)0.000 (3)0.005 (3)
C20.038 (5)0.032 (4)0.025 (4)0.004 (4)0.001 (4)0.005 (3)
C30.043 (6)0.048 (5)0.039 (5)0.005 (4)0.020 (4)0.008 (4)
C40.066 (7)0.034 (5)0.041 (5)0.017 (5)0.023 (5)0.001 (4)
C50.037 (5)0.054 (5)0.022 (4)0.016 (4)0.015 (4)0.016 (4)
C60.036 (4)0.030 (4)0.011 (3)0.004 (4)0.006 (3)0.003 (3)
C70.041 (5)0.025 (4)0.017 (4)0.000 (3)0.009 (3)0.006 (3)
C80.033 (5)0.037 (4)0.019 (4)0.005 (4)0.003 (3)0.006 (3)
C90.049 (6)0.047 (5)0.022 (4)0.009 (5)0.004 (4)0.005 (4)
C100.084 (8)0.064 (6)0.026 (5)0.029 (6)0.000 (5)0.005 (4)
C110.060 (7)0.093 (8)0.033 (5)0.047 (7)0.006 (5)0.011 (5)
C120.038 (5)0.082 (7)0.031 (5)0.001 (5)0.008 (4)0.019 (5)
C130.024 (4)0.057 (5)0.019 (4)0.006 (4)0.001 (3)0.010 (3)
C140.037 (5)0.057 (5)0.028 (4)0.008 (5)0.004 (4)0.004 (4)
C150.028 (4)0.020 (3)0.013 (3)0.005 (3)0.003 (3)0.004 (3)
C160.030 (5)0.032 (4)0.022 (4)0.008 (4)0.001 (3)0.003 (3)
C170.032 (5)0.037 (4)0.022 (4)0.002 (4)0.003 (4)0.000 (3)
C180.039 (5)0.023 (3)0.026 (4)0.009 (4)0.010 (3)0.002 (3)
C190.009 (3)0.019 (3)0.014 (3)0.004 (3)0.004 (3)0.007 (3)
C200.028 (4)0.021 (3)0.016 (3)0.003 (3)0.005 (3)0.003 (3)
C210.025 (4)0.023 (3)0.019 (3)0.000 (3)0.005 (3)0.001 (3)
C220.024 (4)0.033 (4)0.013 (3)0.002 (3)0.002 (3)0.000 (3)
C230.031 (5)0.035 (4)0.020 (4)0.001 (4)0.001 (3)0.004 (3)
C240.036 (5)0.030 (4)0.038 (5)0.008 (4)0.008 (4)0.005 (3)
C250.023 (4)0.051 (5)0.029 (4)0.008 (4)0.004 (4)0.004 (4)
C260.021 (4)0.048 (5)0.024 (4)0.007 (4)0.001 (3)0.002 (3)
C270.020 (4)0.028 (4)0.024 (4)0.001 (3)0.004 (3)0.001 (3)
C280.024 (5)0.036 (4)0.044 (5)0.001 (4)0.011 (4)0.001 (4)
N10.027 (3)0.037 (3)0.015 (3)0.006 (3)0.005 (3)0.006 (3)
N20.023 (3)0.023 (3)0.024 (3)0.001 (3)0.003 (3)0.002 (2)
Geometric parameters (Å, º) top
Hg1—C12.080 (7)C14—H14C0.96
Hg1—C152.095 (6)C15—C161.370 (9)
C1—C21.382 (10)C15—C201.423 (9)
C1—C61.427 (10)C16—C171.383 (9)
C2—C31.390 (10)C16—H160.93
C2—H20.93C17—C181.379 (10)
C3—C41.387 (11)C17—H170.93
C3—H30.93C18—C191.381 (9)
C4—C51.376 (11)C18—H180.93
C4—H40.93C19—C201.371 (8)
C5—C61.367 (9)C19—H190.93
C5—H50.93C20—C211.480 (9)
C6—C71.446 (10)C21—N21.270 (8)
C7—N11.274 (8)C21—H210.93
C7—H70.93C22—C271.388 (9)
C8—C131.379 (10)C22—C231.404 (9)
C8—C91.403 (10)C22—N21.435 (8)
C8—N11.415 (9)C23—C241.365 (10)
C9—C101.386 (12)C23—H230.93
C9—H90.93C24—C251.368 (10)
C10—C111.370 (14)C24—H240.93
C10—H100.93C25—C261.386 (10)
C11—C121.374 (13)C25—H250.93
C11—H110.93C26—C271.397 (10)
C12—C131.410 (10)C26—H260.93
C12—H120.93C27—C281.502 (10)
C13—C141.496 (10)C28—H28A0.96
C14—H14A0.96C28—H28B0.96
C14—H14B0.96C28—H28C0.96
C1—Hg1—C15176.5 (2)C16—C15—Hg1123.1 (5)
C2—C1—C6116.5 (6)C20—C15—Hg1119.7 (5)
C2—C1—Hg1122.3 (5)C15—C16—C17123.1 (7)
C6—C1—Hg1121.2 (5)C15—C16—H16118.5
C1—C2—C3122.9 (7)C17—C16—H16118.5
C1—C2—H2118.5C18—C17—C16119.0 (7)
C3—C2—H2118.5C18—C17—H17120.5
C4—C3—C2119.1 (8)C16—C17—H17120.5
C4—C3—H3120.5C17—C18—C19119.3 (6)
C2—C3—H3120.5C17—C18—H18120.4
C5—C4—C3119.0 (7)C19—C18—H18120.4
C5—C4—H4120.5C20—C19—C18121.6 (6)
C3—C4—H4120.5C20—C19—H19119.2
C6—C5—C4122.2 (7)C18—C19—H19119.2
C6—C5—H5118.9C19—C20—C15119.7 (6)
C4—C5—H5118.9C19—C20—C21117.5 (6)
C5—C6—C1120.1 (7)C15—C20—C21122.5 (6)
C5—C6—C7117.7 (6)N2—C21—C20123.4 (6)
C1—C6—C7122.2 (6)N2—C21—H21118.3
N1—C7—C6125.0 (6)C20—C21—H21118.3
N1—C7—H7117.5C27—C22—C23120.7 (7)
C6—C7—H7117.5C27—C22—N2117.3 (6)
C13—C8—C9120.8 (7)C23—C22—N2121.9 (6)
C13—C8—N1118.4 (6)C24—C23—C22120.2 (7)
C9—C8—N1120.7 (7)C24—C23—H23119.9
C10—C9—C8120.0 (9)C22—C23—H23119.9
C10—C9—H9120C23—C24—C25119.9 (7)
C8—C9—H9120C23—C24—H24120
C11—C10—C9118.8 (9)C25—C24—H24120
C11—C10—H10120.6C24—C25—C26120.5 (7)
C9—C10—H10120.6C24—C25—H25119.8
C10—C11—C12122.3 (9)C26—C25—H25119.8
C10—C11—H11118.9C25—C26—C27121.0 (7)
C12—C11—H11118.9C25—C26—H26119.5
C11—C12—C13119.6 (9)C27—C26—H26119.5
C11—C12—H12120.2C22—C27—C26117.6 (6)
C13—C12—H12120.2C22—C27—C28121.7 (6)
C8—C13—C12118.5 (8)C26—C27—C28120.7 (6)
C8—C13—C14121.0 (7)C27—C28—H28A109.5
C12—C13—C14120.4 (8)C27—C28—H28B109.5
C13—C14—H14A109.5H28A—C28—H28B109.5
C13—C14—H14B109.5C27—C28—H28C109.5
H14A—C14—H14B109.5H28A—C28—H28C109.5
C13—C14—H14C109.5H28B—C28—H28C109.5
H14A—C14—H14C109.5C7—N1—C8120.4 (6)
H14B—C14—H14C109.5C21—N2—C22119.0 (6)
C16—C15—C20117.1 (6)
C6—C1—C2—C30.8 (10)C16—C17—C18—C192.8 (10)
Hg1—C1—C2—C3178.1 (6)C17—C18—C19—C204.3 (10)
C1—C2—C3—C41.1 (11)C18—C19—C20—C154.0 (10)
C2—C3—C4—C51.3 (12)C18—C19—C20—C21178.1 (6)
C3—C4—C5—C64.0 (12)C16—C15—C20—C192.2 (9)
C4—C5—C6—C14.2 (12)Hg1—C15—C20—C19178.7 (5)
C4—C5—C6—C7174.8 (7)C16—C15—C20—C21176.0 (6)
C2—C1—C6—C51.8 (10)Hg1—C15—C20—C214.9 (8)
Hg1—C1—C6—C5179.3 (6)C19—C20—C21—N2163.7 (6)
C2—C1—C6—C7177.3 (6)C15—C20—C21—N210.2 (10)
Hg1—C1—C6—C71.7 (9)C27—C22—C23—C240.1 (10)
C5—C6—C7—N1178.0 (7)N2—C22—C23—C24177.7 (6)
C1—C6—C7—N13.0 (11)C22—C23—C24—C251.0 (11)
C13—C8—C9—C101.8 (11)C23—C24—C25—C261.7 (11)
N1—C8—C9—C10175.3 (6)C24—C25—C26—C271.4 (11)
C8—C9—C10—C112.5 (12)C23—C22—C27—C260.4 (10)
C9—C10—C11—C121.5 (13)N2—C22—C27—C26178.1 (6)
C10—C11—C12—C130.4 (13)C23—C22—C27—C28179.7 (6)
C9—C8—C13—C120.1 (10)N2—C22—C27—C282.6 (10)
N1—C8—C13—C12177.3 (6)C25—C26—C27—C220.3 (10)
C9—C8—C13—C14178.2 (7)C25—C26—C27—C28179.0 (7)
N1—C8—C13—C144.6 (10)C6—C7—N1—C8176.0 (6)
C11—C12—C13—C81.2 (11)C13—C8—N1—C7126.5 (7)
C11—C12—C13—C14179.3 (7)C9—C8—N1—C756.3 (9)
C20—C15—C16—C170.9 (10)C20—C21—N2—C22179.9 (6)
Hg1—C15—C16—C17180.0 (5)C27—C22—N2—C21135.0 (7)
C15—C16—C17—C181.2 (11)C23—C22—N2—C2147.3 (9)

Experimental details

Crystal data
Chemical formula[Hg(C14H12N)2]
Mr589.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.9925 (3), 11.3864 (3), 16.6542 (5)
β (°) 97.673 (1)
V3)2253.79 (11)
Z4
Radiation typeMo Kα
µ (mm1)6.85
Crystal size (mm)0.2 × 0.15 × 0.05
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.254, 0.707
No. of measured, independent and
observed [I > 2σ(I)] reflections
14711, 5084, 3476
Rint0.086
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.092, 1.02
No. of reflections5084
No. of parameters283
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.54, 1.64

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

We thank the EPSRC Crystallographic Service, University of Southampton, for collecting the data.

References

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