Di-chlorido-(4-{[(quinolin-2-yl)methyl-idene]amino}phenol-κ(2) N,N')mercury(II).

In the mononuclear title complex, [HgCl2(C16H12N2O)], synthesized from the phenolic Schiff base 4-[(quinolin-2-yl-methyl-idene)amino]-phenol (QMAP), the coordination geometry around Hg(2+) is distorted tetra-hedral, 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 inter-actions [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 = 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

Δρmax = 0.65 e Å−3

Δρmin = −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 ▶).

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

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

CCDC reference: 994407

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

[HgCl2(C16H12N2O)]	F(000) = 976
Mr = 519.77	Dx = 2.291 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 999 reflections
a = 7.539 (5) Å	θ = 1.8–25.5°
b = 18.551 (5) Å	µ = 10.57 mm−1
c = 10.806 (5) Å	T = 100 K
β = 94.380 (5)°	Needle, yellow
V = 1506.9 (13) Å3	0.29 × 0.19 × 0.12 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2967 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.143, Tmax = 0.352	k = −22→22
11156 measured reflections	l = −13→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.016	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.035	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0146P)2 + 0.8024P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.65 e Å−3
1 restraint	Δρmin = −0.40 e Å−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.

	x	y	z	Uiso*/Ueq
C1	0.7674 (4)	1.15360 (15)	−0.3705 (3)	0.0140 (6)
C2	0.8429 (4)	1.17912 (16)	−0.2579 (3)	0.0147 (6)
H2	0.8987	1.2238	−0.2535	0.018*
C3	0.8345 (4)	1.13750 (15)	−0.1520 (3)	0.0143 (6)
H3	0.8842	1.1548	−0.0764	0.017*
C4	0.7528 (4)	1.07023 (15)	−0.1574 (3)	0.0124 (6)
C5	0.6783 (4)	1.04481 (16)	−0.2710 (3)	0.0141 (6)
H5	0.6235	0.9999	−0.2757	0.017*
C6	0.6857 (4)	1.08617 (15)	−0.3766 (3)	0.0140 (6)
H6	0.6359	1.0689	−0.4522	0.017*
C7	0.6910 (4)	0.96599 (16)	−0.0438 (3)	0.0124 (6)
C8	0.6931 (4)	0.92330 (15)	0.0707 (3)	0.0120 (6)
C9	0.6343 (4)	0.85181 (15)	0.0639 (3)	0.0135 (6)
H9	0.5937	0.8318	−0.0119	0.016*
C10	0.6374 (4)	0.81183 (16)	0.1701 (3)	0.0150 (6)
H10	0.5981	0.7643	0.1671	0.018*
C11	0.6999 (4)	0.84260 (15)	0.2837 (3)	0.0132 (6)
C12	0.7564 (4)	0.91591 (15)	0.2848 (3)	0.0116 (6)
C13	0.8157 (4)	0.94846 (16)	0.3981 (3)	0.0153 (6)
H13	0.8537	0.9962	0.3994	0.018*
C14	0.8176 (4)	0.91016 (16)	0.5057 (3)	0.0176 (7)
H14	0.8556	0.9323	0.5803	0.021*
C15	0.7628 (4)	0.83733 (16)	0.5061 (3)	0.0180 (7)
H15	0.7656	0.8119	0.5804	0.022*
C16	0.7061 (4)	0.80451 (16)	0.3977 (3)	0.0163 (6)
H16	0.6709	0.7565	0.3984	0.020*
N1	0.7487 (3)	1.03052 (12)	−0.0449 (2)	0.0113 (5)
N2	0.7526 (3)	0.95410 (13)	0.1765 (2)	0.0117 (5)
O1	0.7768 (3)	1.19596 (11)	−0.47207 (19)	0.0199 (5)
H1	0.7324	1.1748	−0.5334	0.030*
Hg1	0.832221 (15)	1.069766 (6)	0.162214 (10)	0.01536 (4)
Cl1	1.07921 (9)	1.14792 (4)	0.18122 (6)	0.01560 (15)
Cl2	0.59358 (10)	1.13188 (4)	0.27415 (7)	0.01732 (15)
H7	0.6500	0.9430	−0.1160	0.0140*

	U11	U22	U33	U12	U13	U23
C1	0.0159 (15)	0.0118 (15)	0.0148 (14)	0.0042 (12)	0.0041 (12)	0.0050 (12)
C2	0.0147 (15)	0.0108 (15)	0.0188 (16)	0.0003 (12)	0.0022 (12)	0.0008 (12)
C3	0.0151 (15)	0.0153 (15)	0.0127 (14)	0.0015 (12)	0.0023 (12)	−0.0007 (12)
C4	0.0112 (14)	0.0138 (15)	0.0123 (14)	0.0043 (12)	0.0019 (11)	0.0004 (12)
C5	0.0157 (15)	0.0112 (14)	0.0154 (15)	−0.0003 (12)	0.0006 (12)	0.0001 (12)
C6	0.0163 (15)	0.0153 (16)	0.0103 (14)	0.0007 (12)	0.0008 (12)	−0.0011 (11)
C7	0.0122 (14)	0.0133 (15)	0.0116 (14)	0.0012 (12)	0.0011 (12)	−0.0029 (12)
C8	0.0099 (13)	0.0120 (15)	0.0142 (14)	0.0011 (12)	0.0011 (11)	−0.0008 (12)
C9	0.0154 (15)	0.0129 (15)	0.0122 (14)	−0.0018 (12)	0.0000 (12)	−0.0045 (12)
C10	0.0176 (15)	0.0090 (14)	0.0191 (15)	−0.0002 (12)	0.0052 (13)	−0.0016 (12)
C11	0.0132 (14)	0.0133 (15)	0.0134 (14)	0.0022 (12)	0.0034 (12)	−0.0010 (12)
C12	0.0100 (13)	0.0138 (15)	0.0114 (14)	0.0019 (11)	0.0033 (11)	0.0012 (11)
C13	0.0171 (15)	0.0106 (15)	0.0180 (15)	−0.0021 (12)	0.0009 (13)	−0.0001 (12)
C14	0.0237 (16)	0.0167 (16)	0.0121 (15)	−0.0006 (13)	−0.0014 (13)	−0.0023 (12)
C15	0.0221 (16)	0.0180 (16)	0.0135 (15)	0.0005 (13)	−0.0003 (13)	0.0046 (12)
C16	0.0211 (16)	0.0096 (15)	0.0183 (16)	−0.0006 (12)	0.0029 (13)	0.0019 (12)
N1	0.0116 (12)	0.0109 (13)	0.0114 (12)	0.0011 (10)	0.0018 (10)	−0.0005 (10)
N2	0.0120 (12)	0.0088 (12)	0.0143 (12)	0.0006 (10)	0.0008 (10)	0.0005 (10)
O1	0.0322 (13)	0.0140 (11)	0.0134 (10)	−0.0044 (10)	0.0012 (10)	0.0040 (9)
Hg1	0.02022 (7)	0.01239 (6)	0.01368 (6)	−0.00471 (5)	0.00259 (4)	−0.00206 (5)
Cl1	0.0152 (3)	0.0146 (4)	0.0169 (3)	−0.0022 (3)	0.0008 (3)	−0.0007 (3)
Cl2	0.0177 (4)	0.0182 (4)	0.0161 (4)	0.0002 (3)	0.0018 (3)	−0.0042 (3)

C1—O1	1.356 (3)	C10—C11	1.402 (4)
C1—C2	1.386 (4)	C10—H10	0.9300
C1—C6	1.394 (4)	C11—C16	1.418 (4)
C2—C3	1.386 (4)	C11—C12	1.425 (4)
C2—H2	0.9300	C12—N2	1.366 (4)
C3—C4	1.391 (4)	C12—C13	1.407 (4)
C3—H3	0.9300	C13—C14	1.363 (4)
C4—C5	1.393 (4)	C13—H13	0.9300
C4—N1	1.424 (4)	C14—C15	1.413 (4)
C5—C6	1.379 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.360 (4)
C6—H6	0.9300	C15—H15	0.9300
C7—N1	1.274 (4)	C16—H16	0.9300
C7—C8	1.469 (4)	N1—Hg1	2.392 (2)
C7—H7	0.9170	N2—Hg1	2.237 (2)
C8—N2	1.325 (4)	O1—H1	0.8200
C8—C9	1.398 (4)	Hg1—Cl1	2.3565 (12)
C9—C10	1.365 (4)	Hg1—Cl2	2.5219 (12)
C9—H9	0.9300
O1—C1—C2	118.0 (3)	C10—C11—C12	118.4 (3)
O1—C1—C6	122.2 (3)	C16—C11—C12	118.6 (3)
C2—C1—C6	119.9 (3)	N2—C12—C13	120.5 (3)
C3—C2—C1	119.5 (3)	N2—C12—C11	120.1 (3)
C3—C2—H2	120.2	C13—C12—C11	119.5 (3)
C1—C2—H2	120.2	C14—C13—C12	120.1 (3)
C2—C3—C4	120.9 (3)	C14—C13—H13	120.0
C2—C3—H3	119.6	C12—C13—H13	120.0
C4—C3—H3	119.6	C13—C14—C15	121.1 (3)
C3—C4—C5	119.2 (3)	C13—C14—H14	119.4
C3—C4—N1	117.8 (2)	C15—C14—H14	119.4
C5—C4—N1	122.9 (3)	C16—C15—C14	119.9 (3)
C6—C5—C4	120.1 (3)	C16—C15—H15	120.1
C6—C5—H5	119.9	C14—C15—H15	120.1
C4—C5—H5	119.9	C15—C16—C11	120.8 (3)
C5—C6—C1	120.4 (3)	C15—C16—H16	119.6
C5—C6—H6	119.8	C11—C16—H16	119.6
C1—C6—H6	119.8	C7—N1—C4	121.6 (2)
N1—C7—C8	122.2 (3)	C7—N1—Hg1	110.07 (19)
N1—C7—H7	121.0	C4—N1—Hg1	128.32 (18)
C8—C7—H7	116.0	C8—N2—C12	119.9 (2)
N2—C8—C9	122.6 (3)	C8—N2—Hg1	115.40 (19)
N2—C8—C7	118.4 (3)	C12—N2—Hg1	124.64 (19)
C9—C8—C7	119.0 (3)	C1—O1—H1	109.5
C10—C9—C8	119.1 (3)	N2—Hg1—Cl1	143.01 (6)
C10—C9—H9	120.4	N2—Hg1—N1	73.73 (8)
C8—C9—H9	120.5	Cl1—Hg1—N1	114.76 (6)
C9—C10—C11	119.8 (3)	N2—Hg1—Cl2	101.54 (7)
C9—C10—H10	120.1	Cl1—Hg1—Cl2	105.37 (4)
C11—C10—H10	120.1	N1—Hg1—Cl2	116.19 (6)
C10—C11—C16	123.0 (3)
O1—C1—C2—C3	179.5 (3)	C12—C11—C16—C15	0.7 (4)
C6—C1—C2—C3	−0.7 (4)	C8—C7—N1—C4	177.3 (3)
C1—C2—C3—C4	0.6 (4)	C8—C7—N1—Hg1	−4.5 (3)
C2—C3—C4—C5	−0.2 (4)	C3—C4—N1—C7	−173.5 (3)
C2—C3—C4—N1	−179.8 (3)	C5—C4—N1—C7	6.8 (4)
C3—C4—C5—C6	−0.1 (4)	C3—C4—N1—Hg1	8.6 (4)
N1—C4—C5—C6	179.5 (3)	C5—C4—N1—Hg1	−171.1 (2)
C4—C5—C6—C1	−0.1 (4)	C9—C8—N2—C12	−0.6 (4)
O1—C1—C6—C5	−179.7 (3)	C7—C8—N2—C12	180.0 (2)
C2—C1—C6—C5	0.5 (4)	C9—C8—N2—Hg1	−178.6 (2)
N1—C7—C8—N2	2.0 (4)	C7—C8—N2—Hg1	2.1 (3)
N1—C7—C8—C9	−177.4 (3)	C13—C12—N2—C8	−178.7 (3)
N2—C8—C9—C10	0.2 (4)	C11—C12—N2—C8	1.3 (4)
C7—C8—C9—C10	179.5 (3)	C13—C12—N2—Hg1	−1.0 (4)
C8—C9—C10—C11	−0.3 (4)	C11—C12—N2—Hg1	178.98 (19)
C9—C10—C11—C16	179.7 (3)	C8—N2—Hg1—Cl1	−112.83 (19)
C9—C10—C11—C12	0.9 (4)	C12—N2—Hg1—Cl1	69.4 (2)
C10—C11—C12—N2	−1.4 (4)	C8—N2—Hg1—N1	−3.10 (19)
C16—C11—C12—N2	179.8 (3)	C12—N2—Hg1—N1	179.1 (2)
C10—C11—C12—C13	178.5 (3)	C8—N2—Hg1—Cl2	111.08 (19)
C16—C11—C12—C13	−0.3 (4)	C12—N2—Hg1—Cl2	−66.7 (2)
N2—C12—C13—C14	179.4 (3)	C7—N1—Hg1—N2	3.94 (18)
C11—C12—C13—C14	−0.5 (4)	C4—N1—Hg1—N2	−178.0 (2)
C12—C13—C14—C15	0.9 (5)	C7—N1—Hg1—Cl1	145.35 (17)
C13—C14—C15—C16	−0.4 (5)	C4—N1—Hg1—Cl1	−36.6 (2)
C14—C15—C16—C11	−0.4 (5)	C7—N1—Hg1—Cl2	−91.15 (19)
C10—C11—C16—C15	−178.0 (3)	C4—N1—Hg1—Cl2	87.0 (2)

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

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

Symmetry codes: (i) ; (ii) .