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

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Crystal structure of catena-poly[1,3-di­benzyl­benzimidazolium [[chlorido­mercurate(II)]-di-μ-chlorido]]

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Frères Montouri Constantine, 25000, Algeria, bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria, cLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR; Université Frères Montouri Constantine, 25000 Constantine, Algeria, and dDépartement de Chimie, Université frères Montouri Constantine, 25000 , Algeria
*Correspondence e-mail: bouacida_sofiane@yahoo.fr

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 November 2015; accepted 6 December 2015; online 12 December 2015)

The asymmetric unit of the polymeric title compound, {(C21H19N2)[HgCl3]}n, comprises one-half of the cationic mol­ecule, the other half being generated by application of twofold rotation symmetry, one Hg and two Cl atoms. The HgII atom, lying on a twofold rotation axis, exhibits a distorted triangular coordination environment and is surrounded by three Cl atoms with Hg—Cl distances in the range 2.359 (2)–2.4754 (13) Å. Two additional longer distances [Hg⋯Cl = 3.104 (14) Å] lead to the formation of polymeric [HgCl1/1Cl4/2] chains extending along [001]. The crystal packing can be described by cationic layers alternating parallel to (-110) with the anionic chains located between the layers. The packing is consolidated by ππ stacking inter­actions between the benzene rings of the central benzimidazole entities, with centroid-to-centroid distances of 3.643 (3) Å.

1. Related literature

Benzimidazoles and their derivatives show anti-oxidant (Kuş et al., 2004[Kuş, C., Ayhan-Kilcigil, G., Can Eke, B. & Işcan, M. (2004). Arch. Pharm. Res. 27, 156-163.]), anti­fungal (Preston, 1974[Preston, P. N. (1974). Chem. Rev. 74, 279-314.]) and anthelminthic (Hazelton et al., 1995[Hazelton, J. C., Iddon, B., Suschitzky, H. & Woolley, L. H. (1995). Tetrahedron, 51, 10771-10794.]) properties and have applications in pharmacy and agriculture (Malek et al., 2006[Malek, K., Puc, A., Schroeder, G., Rybachenko, V. I. & Proniewicz, L. M. (2006). Chem. Phys. 327, 439-451.]). They can also be used as ep­oxy resin curing agents, catalysts, metallic surface treatment agents (Li et al., 2003[Li, Q. F., He, R. H., Jensen, J. O. & Bjerrum, N. J. (2003). Chem. Mater. 15, 4896-4915.]; Abboud et al., 2006[Abboud, Y., Abourriche, A., Saffaj, T., Berrada, M., Charrouf, M., Bennamara, A., Cherqaoui, A. & Takky, D. (2006). Appl. Surf. Sci. 252, 8178-8184.]) or as ionic liquids (Li et al., 2011[Li, W., Wang, Y., Wang, Z., Dai, L. & Wang, Y. (2011). Catal. Lett. 141, 1651-1658.]; Chen et al., 2008[Chen, S.-H., Zhao, Q. & Xu, X.-W. (2008). J. Chem. Sci. 120, 481-483.]). For the importance of transition metals ions in biological processes, see: Kaim & Schwederski (1994[Kaim, W. & Schwederski, B. (1994). In Bioinorganic chemistry: inorganic elements in the chemistry of life, an introduction and guide, Inorganic Chemistry: A Textbook series. Chichester: John Wiley & Sons.]). For bond lengths of delocalized systems, see: Ennajih et al. (2009[Ennajih, H., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o2321.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • (C21H19N2)[HgCl3]

  • Mr = 606.32

  • Monoclinic, C 2/c

  • a = 20.3669 (11) Å

  • b = 14.8837 (7) Å

  • c = 7.2154 (4) Å

  • β = 104.372 (2)°

  • V = 2118.79 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 7.65 mm−1

  • T = 295 K

  • 0.19 × 0.11 × 0.05 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.646, Tmax = 0.746

  • 8306 measured reflections

  • 2401 independent reflections

  • 1571 reflections with I > 2σ(I)

  • Rint = 0.042

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.085

  • S = 1.00

  • 2401 reflections

  • 124 parameters

  • H-atom parameters constrained

  • Δρmax = 2.02 e Å−3

  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Related literature top

Benzimidazoles and their derivatives show anti-oxidant (Kuş et al., 2004), antifungal (Preston, 1974) and anthelminthic (Hazelton et al., 1995) properties and have applications in pharmacy and agriculture (Malek et al., 2006). They can also be used as epoxy resin curing agents, catalysts, metallic surface treatment agents (Li et al., 2003; Abboud et al., 2006) or as ionic liquids (Li et al., 2011; Chen et al., 2008). For the importance of transition metals ions in biological processes, see: Kaim & Schwederski (1994). For bond lengths of delocalized systems, see: Ennajih et al. (2009).

Experimental top

1,3-Dibenzylbenzimidazolium trichloridomercurate(II) was synthesized by reaction of 1 mmol of 1,3-dibenzylbenzimidazolium chloride with 1 mmol of mercury(II) chloride in methanol at room temperature. The solid obtained was recrystallized in methanol to yield yellow crystals of the title compound suitable for X-ray diffraction.

Refinement top

H atoms were localized from difference maps but were modelled in calculated positions and treated as riding on their parent atom with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(Caromatic or Cmethylene).

Structure description top

Benzimidazoles and their derivatives show anti-oxidant (Kuş et al., 2004), antifungal (Preston, 1974) and anthelminthic (Hazelton et al., 1995) properties and have applications in pharmacy and agriculture (Malek et al., 2006). They can also be used as epoxy resin curing agents, catalysts, metallic surface treatment agents (Li et al., 2003; Abboud et al., 2006) or as ionic liquids (Li et al., 2011; Chen et al., 2008). For the importance of transition metals ions in biological processes, see: Kaim & Schwederski (1994). For bond lengths of delocalized systems, see: Ennajih et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structures of the entities in the title compound. Displacement ellipsoids are drawn at the 50% probability level; H atoms are represented as small spheres of arbitrary radius. Non-labelled atoms are generated by symmetry code 2 - x, y, 3/2 - z for the cation and by symmetry code 2 - x, y, 1/2 - z for the anion.
[Figure 2] Fig. 2. The polymeric anionic [HgCl1/1Cl4/2]- chain defined by long Hg—Cl distances (in dashed lines).
[Figure 3] Fig. 3. The crystal packing of the title compound viewed down [010] showing alternating layers of cations and anions.
[Figure 4] Fig. 4. The crystal packing of the title compound viewed down [001] (chain direction).
catena-Poly[1,3-dibenzylbenzimidazolium [[chloridomercurate(II)]-di-µ-chlorido]] top
Crystal data top
(C21H19N2)[HgCl3]F(000) = 1160
Mr = 606.32Dx = 1.901 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2352 reflections
a = 20.3669 (11) Åθ = 2.7–22.8°
b = 14.8837 (7) ŵ = 7.65 mm1
c = 7.2154 (4) ÅT = 295 K
β = 104.372 (2)°Prism, yellow
V = 2118.79 (19) Å30.19 × 0.11 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2401 independent reflections
Radiation source: Enraf Nonius FR5901571 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
CCD rotation images, thick slices scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
h = 2626
Tmin = 0.646, Tmax = 0.746k = 1813
8306 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0419P)2]
where P = (Fo2 + 2Fc2)/3
2401 reflections(Δ/σ)max = 0.002
124 parametersΔρmax = 2.02 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
(C21H19N2)[HgCl3]V = 2118.79 (19) Å3
Mr = 606.32Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.3669 (11) ŵ = 7.65 mm1
b = 14.8837 (7) ÅT = 295 K
c = 7.2154 (4) Å0.19 × 0.11 × 0.05 mm
β = 104.372 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
2401 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2011)
1571 reflections with I > 2σ(I)
Tmin = 0.646, Tmax = 0.746Rint = 0.042
8306 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.00Δρmax = 2.02 e Å3
2401 reflectionsΔρmin = 0.41 e Å3
124 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Hg110.050020 (19)0.250.05935 (16)
Cl20.91850 (7)0.05454 (8)0.33958 (18)0.0473 (3)
Cl110.20850 (14)0.250.0888 (9)
N10.9472 (2)0.3140 (3)0.6672 (6)0.0415 (10)
C410.2622 (5)0.750.0484 (19)
H410.19980.750.058*
C60.8265 (3)0.3186 (3)0.6596 (8)0.0446 (13)
C30.9676 (2)0.4034 (3)0.6988 (6)0.0348 (11)
C10.9672 (3)0.5616 (3)0.6966 (8)0.0463 (14)
H10.94580.61650.66130.056*
C20.9314 (3)0.4838 (4)0.6393 (7)0.0418 (12)
H20.88680.48410.56670.05*
C50.8795 (3)0.2814 (4)0.5694 (8)0.0524 (14)
H5A0.87890.21630.57490.063*
H5B0.86940.2990.43590.063*
C70.8324 (3)0.3053 (4)0.8527 (9)0.0569 (15)
H70.86830.27210.92580.068*
C110.7722 (3)0.3668 (4)0.5561 (9)0.0574 (15)
H110.7680.37640.42630.069*
C80.7847 (4)0.3418 (5)0.9352 (9)0.0751 (19)
H80.78930.33421.06580.09*
C90.7303 (3)0.3891 (5)0.8308 (12)0.075 (2)
H90.69820.41270.88940.091*
C100.7238 (3)0.4013 (4)0.6396 (12)0.0695 (18)
H100.68690.43270.56630.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.0830 (3)0.02880 (19)0.0678 (2)00.02171 (18)0
Cl20.0457 (8)0.0495 (8)0.0472 (7)0.0016 (6)0.0120 (6)0.0026 (6)
Cl10.146 (3)0.0298 (12)0.0719 (15)00.0079 (15)0
N10.037 (3)0.031 (2)0.053 (3)0.0031 (19)0.006 (2)0.0073 (19)
C40.043 (5)0.033 (4)0.068 (5)00.010 (4)0
C60.031 (3)0.032 (3)0.064 (4)0.005 (2)0.002 (3)0.008 (2)
C30.037 (3)0.033 (3)0.036 (3)0.003 (2)0.012 (2)0.003 (2)
C10.055 (3)0.029 (3)0.056 (3)0.011 (2)0.014 (3)0.006 (2)
C20.039 (3)0.042 (3)0.042 (3)0.003 (2)0.006 (2)0.003 (2)
C50.044 (3)0.048 (3)0.059 (3)0.005 (3)0.001 (3)0.018 (3)
C70.042 (4)0.060 (4)0.063 (4)0.004 (3)0.001 (3)0.003 (3)
C110.048 (4)0.056 (4)0.062 (4)0.007 (3)0.001 (3)0.002 (3)
C80.068 (5)0.098 (6)0.062 (4)0.013 (4)0.020 (4)0.012 (4)
C90.052 (4)0.075 (5)0.106 (6)0.007 (4)0.033 (4)0.027 (4)
C100.043 (4)0.053 (4)0.109 (6)0.000 (3)0.012 (4)0.001 (4)
Geometric parameters (Å, º) top
Hg1—Cl12.359 (2)C1—C21.376 (7)
Hg1—Cl2i2.4754 (13)C1—H10.93
Hg1—Cl22.4754 (13)C2—H20.93
N1—C41.336 (6)C5—H5A0.97
N1—C31.397 (6)C5—H5B0.97
N1—C51.466 (6)C7—C81.372 (9)
C4—N1ii1.336 (6)C7—H70.93
C4—H40.93C11—C101.375 (9)
C6—C111.374 (7)C11—H110.93
C6—C71.383 (8)C8—C91.370 (10)
C6—C51.499 (7)C8—H80.93
C3—C3ii1.344 (9)C9—C101.365 (10)
C3—C21.414 (7)C9—H90.93
C1—C1ii1.367 (11)C10—H100.93
Cl1—Hg1—Cl2i128.95 (3)N1—C5—C6111.2 (4)
Cl1—Hg1—Cl2128.95 (3)N1—C5—H5A109.4
Cl2i—Hg1—Cl2102.09 (6)C6—C5—H5A109.4
C4—N1—C3107.6 (4)N1—C5—H5B109.4
C4—N1—C5125.5 (4)C6—C5—H5B109.4
C3—N1—C5126.8 (4)H5A—C5—H5B108
N1ii—C4—N1109.7 (6)C8—C7—C6119.1 (6)
N1ii—C4—H4125.2C8—C7—H7120.4
N1—C4—H4125.2C6—C7—H7120.4
C11—C6—C7118.7 (6)C6—C11—C10121.7 (6)
C11—C6—C5121.8 (5)C6—C11—H11119.2
C7—C6—C5119.5 (5)C10—C11—H11119.2
C3ii—C3—N1107.5 (3)C9—C8—C7121.9 (6)
C3ii—C3—C2122.2 (3)C9—C8—H8119
N1—C3—C2130.2 (4)C7—C8—H8119
C1ii—C1—C2122.7 (3)C10—C9—C8119.1 (6)
C1ii—C1—H1118.7C10—C9—H9120.4
C2—C1—H1118.7C8—C9—H9120.4
C1—C2—C3115.1 (5)C9—C10—C11119.5 (6)
C1—C2—H2122.5C9—C10—H10120.2
C3—C2—H2122.5C11—C10—H10120.2
C3—N1—C4—N1ii0.1 (2)C11—C6—C5—N1123.0 (5)
C5—N1—C4—N1ii177.2 (5)C7—C6—C5—N156.1 (7)
C4—N1—C3—C3ii0.2 (6)C11—C6—C7—C81.0 (8)
C5—N1—C3—C3ii177.1 (5)C5—C6—C7—C8178.1 (5)
C4—N1—C3—C2179.0 (4)C7—C6—C11—C100.5 (8)
C5—N1—C3—C23.7 (8)C5—C6—C11—C10179.6 (5)
C1ii—C1—C2—C30.0 (9)C6—C7—C8—C91.7 (10)
C3ii—C3—C2—C11.1 (8)C7—C8—C9—C100.8 (10)
N1—C3—C2—C1179.8 (5)C8—C9—C10—C110.7 (10)
C4—N1—C5—C6121.4 (5)C6—C11—C10—C91.3 (9)
C3—N1—C5—C655.4 (7)
Symmetry codes: (i) x+2, y, z+1/2; (ii) x+2, y, z+3/2.

Experimental details

Crystal data
Chemical formula(C21H19N2)[HgCl3]
Mr606.32
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)20.3669 (11), 14.8837 (7), 7.2154 (4)
β (°) 104.372 (2)
V3)2118.79 (19)
Z4
Radiation typeMo Kα
µ (mm1)7.65
Crystal size (mm)0.19 × 0.11 × 0.05
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2011)
Tmin, Tmax0.646, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
8306, 2401, 1571
Rint0.042
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.085, 1.00
No. of reflections2401
No. of parameters124
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.02, 0.41

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).

 

Acknowledgements

Thanks are due to MESRS and DG–RSDT (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et la Direction Générale de la Recherche – Algérie) for financial support.

References

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