Crystal structure of di­chlorido­{N 1-phenyl-N 4-[(quinolin-2-yl-κN)methylidene]benzene-1,4-diamine-κN 4}mercury(II)

Md Serajul Haque Faizi; Elena V Prisyazhnaya; Turganbay S Iskenderov

doi:10.1107/S2056989015001620

. 2015 Jan 31;71(Pt 2):m46–m47. doi: 10.1107/S2056989015001620

Crystal structure of dichlorido{N ¹-phenyl-N ⁴-[(quinolin-2-yl-κN)methylidene]benzene-1,4-diamine-κN ⁴}mercury(II)

Md Serajul Haque Faizi ^a, Elena V Prisyazhnaya ^b,^*, Turganbay S Iskenderov ^c

PMCID: PMC4384595 PMID: 25878849

Abstract

In the mononuclear title complex, [HgCl₂(C₂₂H₁₇N₃)], synthesized from the quinoline-derived Schiff base N ¹-phenyl-N ⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD) and HgCl₂, the coordination sphere around the Hg²⁺ atom is distorted tetrahedral, comprising two Cl atoms [Hg—Cl = 2.3487 (14) and 2.4490 (15) Å] and two N atom donors from the PQMBD ligand, viz. the quinolyl and the imine N atom [Hg—N = 2.270 (4) and 2.346 (4) Å, respectively]. The dihedral angle between the two benzene rings attached to the amino group is 43.7 (3)°. In the crystal, N—H⋯Cl and C—H⋯Cl hydrogen bonds, as well as π–π stacking interactions between one phenyl ring and the pyridine ring of the quinoline moiety of an adjacent molecule [centroid-to-centroid separation = 3.617 (4) Å] are observed, resulting in a three-dimensional network.

Keywords: crystal structure, Schiff base, mercury(II) complex, N—H⋯Cl and C—H⋯Cl hydrogen bonding, π–π stacking interactions

Related literature

For the hazards of mercury in organisms, see: Mandal et al. (2012 ▸). For reports of quinolyl derivatives of Schiff bases, see: Motswainyana et al. (2013 ▸); Das et al. (2013 ▸); Song et al. (2011 ▸); Jursic et al. (2002 ▸). For background to related Schiff base–metal complexes, see: Faizi & Hussain (2014 ▸); Faizi et al. (2014 ▸); Moroz et al. (2012 ▸). For related Hg-containing structures, see: Marjani et al. (2009 ▸); Faizi & Sen (2014 ▸), and for related Schiff base complexes, see: Penkova et al. (2009 ▸, 2010 ▸); Strotmeyer et al. (2003 ▸); Petrusenko et al. (1997 ▸). The amino group of the title compound is separated from the chelating unit which makes this complex a possible precursor for further functionalization, eventually yielding binuclear compounds as reported by Fritsky et al. (1998 ▸, 2006 ▸) and Kanderal et al. (2005 ▸). graphic file with name e-71-00m46-scheme1.jpg

Experimental

Crystal data

[HgCl₂(C₂₂H₁₇N₃)]
M _r = 594.88
Monoclinic,
a = 29.265 (5) Å
b = 7.5671 (13) Å
c = 18.811 (3) Å
β = 99.271 (7)°
V = 4111.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 7.76 mm⁻¹
T = 100 K
0.18 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ▸) T _min = 0.336, T _max = 0.511
22545 measured reflections
5133 independent reflections
3182 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.087
S = 1.00
5133 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: SMART (Bruker, 2003 ▸); cell refinement: SAINT (Bruker, 2003 ▸); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015001620/wm5117sup1.cif

e-71-00m46-sup1.cif^{(26.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015001620/wm5117Isup2.hkl

e-71-00m46-Isup2.hkl^{(246.4KB, hkl)}

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015001620/wm5117fig1.tif

The molecular structure and the atom-numbering scheme of the title complex, with non-H atoms drawn as displacement ellipsoids at the 40% probability level.

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015001620/wm5117fig2.tif

N—H⋯Cl hydrogen bonds between adjacent molecules as viewed along [010].

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015001620/wm5117fig3.tif

The packing of molecules in the title compound, showing intermolecular interactions as dashed lines.

CCDC reference: 1045457

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N3H3ACl2ⁱ	0.86	2.58	3.363(4)	151
C10H10Cl2ⁱⁱ	0.93	2.81	3.679(7)	157
C20H20Cl1ⁱⁱⁱ	0.93	2.80	3.692(11)	160

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

Acknowledgments

The authors are grateful to the Department of Chemistry, IIT Kanpur, Kanpur 208 016, India, for the X-ray data collection.

supplementary crystallographic information

S1. Experimental

The iminoquinolyl ligand N¹-phenyl-N⁴-[(quinolin-2-yl)methylidene]benzene-1,4-diamine (PQMBD) was prepared by reacting 2-quinolinecarboxaldehyde (0.085 g, 0.54 mmol) with one equivalent of N-phenyl-p-phenylenediamine (0.100 g, 0.54 mmol) and was obtained in 88% yield (0.15 g). The obtained compound was characterized by FT–IR, NMR and ESI-mass spectroscopy: IR (KBr, ν / cm^-1): 3417, 3052 (C-H arom), 1620 (C═N), 1515, 1313, 843, 756. ¹H NMR (400 MHz, CDCl₃, δ /p.p.m.): 8.85 (1H, S), 8.37 (1H, d), 8.23 (1H, d), 8.16 (1H, d), 7.86 (1H, d), 7.75 (1H, t), 7.58 (1H, t), 7.40 (2H, d), 7.30 (1H, t), 7.13 (5H, m), 6.51 (1H, t). ESI-MS m/z: 324 (M+1).

PQMBD (0.10 g, 0.31 mmol), mercury(II) chloride (0.08 g, 0.31 mmol) and ethanol (5 ml) were stirred vigorously for 1 h, after which the precipitate was filtered off and redissolved in dimethylformamide. Crystals of the title complex suitable for X-ray analysis was obtained within 3 days by slow evaporation of the DMF solvent.