Di­chlorido­(4-{[(quinolin-2-yl)methyl­idene]amino}phenol-κ2 N,N′)mercury(II)

Md Serajul Haque Faizi; Pratik Sen

doi:10.1107/S1600536814007077

. 2014 Apr 9;70(Pt 5):m173. doi: 10.1107/S1600536814007077

Dichlorido(4-{[(quinolin-2-yl)methylidene]amino}phenol-κ² N,N′)mercury(II)

Md Serajul Haque Faizi ^a, Pratik Sen ^a,^*

PMCID: PMC4011313 PMID: 24860307

Abstract

In the mononuclear title complex, [HgCl₂(C₁₆H₁₂N₂O)], synthesized from the phenolic Schiff base 4-[(quinolin-2-ylmethylidene)amino]phenol (QMAP), the coordination geometry around Hg²⁺ is distorted tetrahedral, comprising two Cl atoms [Hg—Cl = 2.3565 (12) and 2.5219 (12) Å] and two N-atom donors from the QMAP ligand, viz. one imine and the other quinoline [Hg—N = 2.392 (2) and 2.237 (2) Å, respectively]. In the crystal, O—H⋯Cl hydrogen bonds generate a chain structure extending along the c-axis direction. Weak C—H⋯Cl and π–π stacking interactions [minimum ring centroid separation = 3.641 (3) Å] give an overall layered structure lying parallel to (001).

Related literature

For applications of 4-[(quinolin-2-ylmethylene)amino]phenol and related structures, see: Das et al. (2013 ▶); Jursic et al. (2002 ▶). For a related structure, see: Marjani et al. (2009 ▶).

Experimental

Crystal data

[HgCl₂(C₁₆H₁₂N₂O)]
M _r = 519.77
Monoclinic,
a = 7.539 (5) Å
b = 18.551 (5) Å
c = 10.806 (5) Å
β = 94.380 (5)°
V = 1506.9 (13) Å³
Z = 4
Mo Kα radiation
μ = 10.57 mm⁻¹
T = 100 K
0.29 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.143, T _max = 0.352
11156 measured reflections
2967 independent reflections
2679 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.016
wR(F ²) = 0.035
S = 1.05
2967 reflections
200 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.40 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, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND (Brandenberg & Putz, 2006 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007077/zs2293sup1.cif

e-70-0m173-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007077/zs2293Isup2.hkl

e-70-0m173-Isup2.hkl^{(142.7KB, hkl)}

CCDC reference: 994407

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl2ⁱ	0.82	2.39	3.204 (3)	171
C7—H7⋯Cl2ⁱⁱ	0.92	2.78	3.644 (4)	156

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

Acknowledgments

The authors are grateful to the Science and Engineering Research Board, Government of India (project No. SR/S11/PC-08/2011.

supplementary crystallographic information

1. Comment

Quinoline derivatives of Schiff bases are important building blocks of many important compounds widely used in biological applications such as antioxidative and anticancer and fluorescent probe agents in industry and in coordination chemistry (Das et al., 2013; Jursic et al., 2002). The synthesis of polymeric complex of mercury(II) using the quinoline aldehyde derivative of the Schiff base 4-(quinolin-2-ylmethylene)aminophenol (QMAP) has not previously been reported. The title Hg^II complex with QMAP, [Hg(C₁₆H₁₂N₂O)Cl₂] has been synthesized and the structure is reported herein.

In the title mononuclear complex (Fig. 1) the HgCl₂N₂ coordination geometry is distorted tetrahedral, comprising two Cl-atoms [Hg1—Cl1 and Hg1—Cl2 = 2.3565 (12) and 2.5219 (12) Å respectively] and two N-atom donors from the QMAP ligand, one imine [Hg1–N1 = 2.392 (2) Å] and the other quinoline [Hg1—N2 = 2.237 (2) Å]. The observed Hg—Cl and Hg—N bond lengths and bond angles are considered normal for this type of Hg^II complex, e.g., [Hg—N = 2.396 (4) Å] and [Hg—Cl = 2.367 (4) Å] (Marjani et al., 2009). In the crystal, O1—H···Cl2 hydrogen bonds (Table 2) give a one-dimensional chain structure which extends along c (Fig. 2) and weak C7—H···Cl2 hydrogen bonds and π–π ring stacking interactions [minimum ring centroid separation between the inversion related benzene and quinoline rings = 3.641 (3) Å] give an overall two-dimensional layered structure lying parallel to (001) (Fig. 3).

2. Experimental

A mixture of 4-(quinolin-2-ylmethylene)aminophenol (QMAP) (0.10 g, 0.40 mmol), mercury(II) chloride (0.11 g, 0.40 mmol) and ethanol (5 ml) were stirred vigorously for 30 min, after which the precipitate was filtered off and dissolved in dimethylformamide. Crystals of the title complex suitable for X-ray analysis was obtained within 2 days by slow evaporation of the DMF solvent.