Literature DB >> 23125610

Di-μ-chlorido-bis-{chlorido[2,3-dimethyl-N-(pyridin-2-yl-methyl-idene)aniline-κ(2)N,N']mercury(II)}.

Seyed Jalal Hoseyni1, Mohamad Reza Talei Bavil Olyai, Behrouz Notash.   

Abstract

In the centrosymmetric binuclear molecule of the title complex, [Hg(2)Cl(4)(C(14)H(14)N(2))(2)], the five-coordinated Hg(II) ions have a distorted square-pyramidal geometry defined by two N atoms belonging to the chelating imino-pyridine ligand and three Cl atoms. The benzene and pyridine rings are oriented at a dihedral angle of 56.7 (6)°. The crystal packing is stabilized by C-H⋯Cl hydrogen bonds and π-π inter-actions between the pyridine rings [centroid-centroid distance = 3.796 (6) Å].

Entities:  

Year:  2012        PMID： 23125610      PMCID： PMC3470166          DOI： 10.1107/S1600536812039050

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to Schiff base compounds, see: Gibson et al. (2007 ▶); Gibson & Spitzmesser (2003 ▶); Ittel et al. (2000 ▶). For related structures, see: Baul et al. (2004 ▶).

Experimental

Crystal data

[Hg2Cl4(C14H14N2)2] M = 963.52 Monoclinic, a = 7.7989 (16) Å b = 26.525 (5) Å c = 15.098 (3) Å β = 98.26 (3)° V = 3090.9 (11) Å3 Z = 4 Mo Kα radiation μ = 10.29 mm−1 T = 298 K 0.50 × 0.17 × 0.15 mm

Data collection

Stoe IPDS-2T diffractometer Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002 ▶) T min = 0.126, T max = 0.210 12121 measured reflections 4164 independent reflections 3174 reflections with I > 2σ(I) R int = 0.118

Refinement

R[F 2 > 2σ(F 2)] = 0.083 wR(F 2) = 0.206 S = 1.11 4164 reflections 175 parameters H-atom parameters constrained Δρmax = 3.28 e Å−3 Δρmin = −4.88 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039050/hy2585sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039050/hy2585Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Hg2Cl4(C14H14N2)2]F(000) = 1808.0
Mr = 963.52Dx = 2.071 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4164 reflections
a = 7.7989 (16) Åθ = 2.1–29.2°
b = 26.525 (5) ŵ = 10.29 mm−1
c = 15.098 (3) ÅT = 298 K
β = 98.26 (3)°Column, yellow
V = 3090.9 (11) Å30.50 × 0.17 × 0.15 mm
Z = 4
Stoe IPDS-2T diffractometer4164 independent reflections
Radiation source: fine-focus sealed tube3174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.118
Detector resolution: 0.15 mm pixels mm-1θmax = 29.2°, θmin = 2.1°
ω scansh = −10→10
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)k = −36→35
Tmin = 0.126, Tmax = 0.210l = −20→16
12121 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.083H-atom parameters constrained
wR(F2) = 0.206w = 1/[σ2(Fo2) + (0.1219P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
4164 reflectionsΔρmax = 3.28 e Å−3
175 parametersΔρmin = −4.88 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0012 (2)
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.
xyzUiso*/Ueq
Hg10.43296 (5)0.703848 (14)0.98975 (3)0.0525 (2)
Cl20.1308 (3)0.71572 (10)0.88978 (17)0.0524 (5)
Cl10.3754 (4)0.64201 (11)1.0936 (2)0.0663 (7)
N10.5738 (9)0.7612 (3)0.9145 (5)0.0452 (16)
N20.6082 (10)0.6579 (3)0.8873 (6)0.0528 (19)
C50.6666 (12)0.7441 (4)0.8523 (6)0.050 (2)
C60.6903 (13)0.6896 (4)0.8436 (7)0.052 (2)
H60.76560.67760.80600.062*
C80.5112 (14)0.5709 (4)0.8740 (7)0.057 (2)
C70.6450 (14)0.6053 (4)0.8836 (7)0.058 (2)
C10.5528 (15)0.8102 (4)0.9243 (7)0.055 (2)
H10.48870.82140.96780.066*
C130.3227 (15)0.5888 (5)0.8577 (9)0.065 (3)
H13A0.26960.58280.91020.098*
H13B0.26080.57060.80810.098*
H13C0.31940.62420.84450.098*
C120.8192 (15)0.5889 (5)0.8986 (8)0.065 (3)
H120.90930.61220.90650.078*
C90.5443 (17)0.5190 (5)0.8768 (9)0.068 (3)
C20.6211 (14)0.8450 (4)0.8733 (8)0.060 (2)
H20.60300.87920.88140.072*
C40.7403 (13)0.7770 (5)0.7992 (7)0.056 (2)
H40.80510.76490.75660.068*
C30.7178 (14)0.8285 (5)0.8093 (8)0.062 (3)
H30.76690.85150.77360.074*
C140.406 (2)0.4806 (5)0.8639 (13)0.092 (5)
H14A0.32880.48760.80980.138*
H14B0.34180.48140.91380.138*
H14C0.45610.44780.85990.138*
C110.8530 (17)0.5385 (5)0.9014 (10)0.080 (4)
H110.96720.52730.91010.096*
C100.7187 (19)0.5035 (6)0.8912 (10)0.082 (4)
H100.74460.46930.89400.098*
U11U22U33U12U13U23
Hg10.0468 (3)0.0595 (3)0.0521 (3)0.00288 (15)0.00989 (16)0.00296 (15)
Cl20.0445 (11)0.0637 (13)0.0479 (11)0.0022 (10)0.0026 (9)0.0021 (10)
Cl10.0688 (17)0.0655 (14)0.0649 (16)0.0064 (12)0.0102 (13)0.0160 (12)
N10.034 (3)0.064 (4)0.037 (3)−0.003 (3)0.006 (3)−0.009 (3)
N20.041 (4)0.063 (5)0.055 (4)0.007 (4)0.008 (3)−0.013 (4)
C50.039 (4)0.067 (6)0.043 (4)0.002 (4)−0.002 (4)0.000 (4)
C60.039 (4)0.075 (6)0.041 (4)0.002 (4)0.002 (4)−0.006 (4)
C80.055 (5)0.062 (5)0.051 (5)0.009 (5)−0.003 (4)−0.004 (4)
C70.047 (5)0.073 (6)0.053 (5)0.009 (5)0.003 (4)−0.009 (5)
C10.056 (6)0.058 (5)0.053 (5)0.004 (4)0.012 (5)0.003 (4)
C130.054 (6)0.070 (6)0.068 (7)0.001 (5)−0.002 (5)0.001 (5)
C120.052 (6)0.079 (7)0.063 (6)0.020 (5)0.006 (5)−0.010 (5)
C90.066 (7)0.071 (7)0.065 (7)0.001 (6)0.002 (5)0.001 (5)
C20.050 (5)0.062 (6)0.064 (6)−0.004 (5)−0.001 (5)0.004 (5)
C40.041 (5)0.084 (7)0.043 (5)−0.006 (5)0.004 (4)−0.002 (5)
C30.052 (6)0.079 (7)0.053 (5)−0.013 (5)0.003 (5)0.009 (5)
C140.089 (10)0.059 (7)0.125 (14)0.008 (6)0.001 (9)0.001 (8)
C110.057 (7)0.083 (8)0.096 (10)0.019 (6)−0.005 (7)−0.004 (7)
C100.083 (9)0.074 (8)0.084 (9)0.022 (7)−0.003 (7)−0.005 (7)
Hg1—N12.273 (8)C13—H13A0.9600
Hg1—Cl12.356 (3)C13—H13B0.9600
Hg1—N22.521 (8)C13—H13C0.9600
Hg1—Cl22.628 (3)C12—C111.363 (18)
Hg1—Cl2i2.893 (3)C12—H120.9300
N1—C11.322 (14)C9—C101.407 (18)
N1—C51.345 (13)C9—C141.479 (19)
N2—C61.295 (14)C2—C31.379 (17)
N2—C71.426 (14)C2—H20.9300
C5—C41.365 (16)C4—C31.390 (18)
C5—C61.466 (15)C4—H40.9300
C6—H60.9300C3—H30.9300
C8—C71.379 (16)C14—H14A0.9600
C8—C91.400 (17)C14—H14B0.9600
C8—C131.531 (15)C14—H14C0.9600
C7—C121.413 (14)C11—C101.39 (2)
C1—C21.358 (16)C11—H110.9300
C1—H10.9300C10—H100.9300
N1—Hg1—Cl1161.8 (2)C8—C13—H13B109.5
N1—Hg1—N270.9 (3)H13A—C13—H13B109.5
Cl1—Hg1—N2104.1 (2)C8—C13—H13C109.5
N1—Hg1—Cl295.2 (2)H13A—C13—H13C109.5
Cl1—Hg1—Cl2102.99 (10)H13B—C13—H13C109.5
N2—Hg1—Cl2103.1 (2)C11—C12—C7119.0 (13)
N1—Hg1—Cl2i87.7 (2)C11—C12—H12120.5
Cl1—Hg1—Cl2i91.64 (10)C7—C12—H12120.5
N2—Hg1—Cl2i154.2 (2)C8—C9—C10117.5 (12)
Cl2—Hg1—Cl2i92.97 (7)C8—C9—C14123.0 (11)
Hg1—Cl2—Hg1i87.03 (7)C10—C9—C14119.4 (13)
C1—N1—C5119.7 (9)C1—C2—C3118.8 (11)
C1—N1—Hg1121.8 (7)C1—C2—H2120.6
C5—N1—Hg1118.2 (7)C3—C2—H2120.6
C6—N2—C7119.9 (9)C5—C4—C3119.6 (10)
C6—N2—Hg1110.4 (7)C5—C4—H4120.2
C7—N2—Hg1128.9 (7)C3—C4—H4120.2
N1—C5—C4120.7 (10)C2—C3—C4118.5 (10)
N1—C5—C6118.7 (9)C2—C3—H3120.7
C4—C5—C6120.6 (10)C4—C3—H3120.7
N2—C6—C5121.2 (9)C9—C14—H14A109.5
N2—C6—H6119.4C9—C14—H14B109.5
C5—C6—H6119.4H14A—C14—H14B109.5
C7—C8—C9121.0 (11)C9—C14—H14C109.5
C7—C8—C13120.4 (10)H14A—C14—H14C109.5
C9—C8—C13118.6 (11)H14B—C14—H14C109.5
C8—C7—C12120.6 (11)C12—C11—C10120.8 (12)
C8—C7—N2119.9 (9)C12—C11—H11119.6
C12—C7—N2119.3 (10)C10—C11—H11119.6
N1—C1—C2122.7 (11)C11—C10—C9121.2 (12)
N1—C1—H1118.6C11—C10—H10119.4
C2—C1—H1118.6C9—C10—H10119.4
C8—C13—H13A109.5
N1—Hg1—Cl2—Hg1i−88.0 (2)C4—C5—C6—N2−173.4 (9)
Cl1—Hg1—Cl2—Hg1i92.38 (10)C9—C8—C7—C12−1.6 (18)
N2—Hg1—Cl2—Hg1i−159.6 (2)C13—C8—C7—C12−180.0 (11)
Cl2i—Hg1—Cl2—Hg1i0.0C9—C8—C7—N2−175.2 (11)
Cl1—Hg1—N1—C1−105.9 (9)C13—C8—C7—N26.4 (16)
N2—Hg1—N1—C1177.2 (8)C6—N2—C7—C8−137.2 (11)
Cl2—Hg1—N1—C175.2 (7)Hg1—N2—C7—C854.0 (13)
Cl2i—Hg1—N1—C1−17.6 (7)C6—N2—C7—C1249.1 (15)
Cl1—Hg1—N1—C580.8 (9)Hg1—N2—C7—C12−119.7 (10)
N2—Hg1—N1—C53.9 (6)C5—N1—C1—C20.3 (15)
Cl2—Hg1—N1—C5−98.1 (6)Hg1—N1—C1—C2−172.9 (8)
Cl2i—Hg1—N1—C5169.1 (6)C8—C7—C12—C111.6 (19)
N1—Hg1—N2—C60.1 (6)N2—C7—C12—C11175.3 (12)
Cl1—Hg1—N2—C6−161.6 (6)C7—C8—C9—C101.1 (18)
Cl2—Hg1—N2—C691.2 (6)C13—C8—C9—C10179.5 (11)
Cl2i—Hg1—N2—C6−35.8 (10)C7—C8—C9—C14−177.9 (13)
N1—Hg1—N2—C7169.7 (9)C13—C8—C9—C140.5 (19)
Cl1—Hg1—N2—C78.0 (8)N1—C1—C2—C3−0.7 (17)
Cl2—Hg1—N2—C7−99.2 (8)N1—C5—C4—C3−0.5 (14)
Cl2i—Hg1—N2—C7133.8 (7)C6—C5—C4—C3−179.3 (8)
C1—N1—C5—C40.3 (14)C1—C2—C3—C40.5 (16)
Hg1—N1—C5—C4173.8 (7)C5—C4—C3—C20.1 (15)
C1—N1—C5—C6179.1 (8)C7—C12—C11—C10−1 (2)
Hg1—N1—C5—C6−7.5 (11)C12—C11—C10—C91 (2)
C7—N2—C6—C5−174.6 (8)C8—C9—C10—C11−1 (2)
Hg1—N2—C6—C5−3.9 (11)C14—C9—C10—C11178.3 (15)
N1—C5—C6—N27.8 (13)
D—H···AD—HH···AD···AD—H···A
C1—H1···Cl2i0.932.653.400 (11)138
C4—H4···Cl2ii0.932.673.552 (11)158
C14—H14C···Cl1iii0.962.763.685 (14)162
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯Cl2i 0.932.653.400 (11)138
C4—H4⋯Cl2ii 0.932.673.552 (11)158
C14—H14C⋯Cl1iii 0.962.763.685 (14)162

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

  4 in total

1.  Late-metal catalysts for ethylene homo- and copolymerization.

Authors:  S D Ittel; L K Johnson; M Brookhart
Journal:  Chem Rev       Date:  2000-04-12       Impact factor: 60.622

2.  Advances in non-metallocene olefin polymerization catalysis.

Authors:  Vernon C Gibson; Stefan K Spitzmesser
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

Review 3.  Bis(imino)pyridines: surprisingly reactive ligands and a gateway to new families of catalysts.

Authors:  Vernon C Gibson; Carl Redshaw; Gregory A Solan
Journal:  Chem Rev       Date:  2007-05       Impact factor: 60.622

4.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
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  1 in total

1.  Crystal structure of di-μ-chlorido-bis-(chlorido-{N1,N1-diethyl-N4-[(pyridin-2-yl-κN)methyl-idene]benzene-1,4-di-amine-κN4}mercury(II)).

Authors:  Md Serajul Haque Faizi; Necmi Dege; Kateryna Goleva
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-05-05
  1 in total

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