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

In the mononuclear title complex, [HgCl2(C20H21N3)], synthesized from the quinoline-derived Schiff base N (1),N (1)-diethyl-N (4)-(quinolin-2-yl-methyl-idene)benzene-1,4-di-amine (QMBD), the coordination geometry around the Hg(2+) atom is distorted tetra-hedral, comprising two Cl atoms [Hg-Cl = 2.3654 (19) and 2.4394 (18) Å] and two N-atom donors from the QMBD ligand, viz. one imine and quinoline [Hg-N = 2.334 (5) and 2.340 (5) Å, respectively]. In the crystal, weak C-H⋯Cl hydrogen bonds and weak π-π aromatic ring stacking inter-actions [minimum ring-centroid separation = 3.680 (4) Å] give an overall three-dimensional network.

Related literature

For applications of quinolyl imine and related structures, see: Mandal et al. (2012 ▶); Motswainyana et al. (2013 ▶); Das et al. (2013 ▶); Song et al. (2011 ▶); Jursic et al. (2002 ▶); Marjani et al. (2009 ▶); Faizi & Sen (2014 ▶).

Experimental

Crystal data

[HgCl2(C20H21N3)]

M = 574.89

Monoclinic,

a = 8.8522 (19) Å

b = 9.474 (2) Å

c = 23.512 (5) Å

β = 97.446 (4)°

V = 1955.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 8.15 mm−1

T = 100 K

0.26 × 0.18 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.226, T max = 0.417

9875 measured reflections

3438 independent reflections

2979 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.089

S = 1.17

3438 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.91 e Å−3

Δρmin = −1.07 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 (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400957X/zs2295sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400957X/zs2295Isup2.hkl

CCDC reference: 999849

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

[HgCl2(C20H21N3)]	F(000) = 1104
Mr = 574.89	Dx = 1.953 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 999 reflections
a = 8.8522 (19) Å	θ = 2.1–28.2°
b = 9.474 (2) Å	µ = 8.15 mm−1
c = 23.512 (5) Å	T = 100 K
β = 97.446 (4)°	Block, yellow
V = 1955.2 (7) Å3	0.26 × 0.18 × 0.13 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	2979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→7
Tmin = 0.226, Tmax = 0.417	k = −11→11
9875 measured reflections	l = −27→27

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0308P)2 + 10.3789P] where P = (Fo2 + 2Fc2)/3
3438 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 1.91 e Å−3
0 restraints	Δρmin = −1.07 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	0.8207 (7)	0.4421 (7)	1.0240 (3)	0.0184 (10)
C2	0.6971 (8)	0.5234 (7)	0.9970 (3)	0.0225 (15)
H2	0.6564	0.5035	0.9594	0.027*
C3	0.6374 (8)	0.6313 (7)	1.0260 (3)	0.0253 (16)
H3	0.5575	0.6853	1.0078	0.030*
C4	0.6962 (8)	0.6602 (7)	1.0826 (3)	0.0221 (15)
H4	0.6540	0.7326	1.1021	0.027*
C5	0.8150 (9)	0.5836 (7)	1.1100 (3)	0.0268 (16)
H5	0.8521	0.6041	1.1479	0.032*
C6	0.8819 (8)	0.4740 (7)	1.0813 (3)	0.0218 (15)
C7	1.0050 (8)	0.3942 (6)	1.1069 (3)	0.0211 (14)
H7	1.0451	0.4107	1.1448	0.025*
C8	1.0667 (7)	0.2912 (7)	1.0759 (3)	0.0198 (14)
H8	1.1509	0.2398	1.0921	0.024*
C9	0.9991 (8)	0.2638 (6)	1.0179 (3)	0.0171 (14)
C10	1.0694 (7)	0.1553 (7)	0.9856 (3)	0.0184 (10)
C11	1.0772 (7)	0.0274 (6)	0.9004 (3)	0.0169 (13)
C12	1.2176 (8)	−0.0386 (6)	0.9159 (3)	0.0198 (14)
H12	1.2724	−0.0179	0.9514	0.024*
C13	1.2770 (8)	−0.1323 (7)	0.8809 (3)	0.0230 (15)
H13	1.3710	−0.1732	0.8933	0.028*
C14	1.2006 (8)	−0.1695 (7)	0.8265 (3)	0.0201 (14)
C15	1.0599 (7)	−0.1020 (6)	0.8098 (3)	0.0167 (13)
H15	1.0055	−0.1227	0.7742	0.020*
C16	1.0010 (8)	−0.0056 (7)	0.8452 (3)	0.0190 (14)
H16	0.9091	0.0388	0.8325	0.023*
C17	1.4009 (8)	−0.3421 (7)	0.8108 (3)	0.0236 (15)
H17A	1.3981	−0.4306	0.7899	0.028*
H17B	1.4031	−0.3645	0.8512	0.028*
C18	1.5448 (9)	−0.2657 (7)	0.8027 (4)	0.0333 (19)
H18A	1.6310	−0.3233	0.8165	0.050*
H18B	1.5498	−0.1786	0.8237	0.050*
H18C	1.5457	−0.2462	0.7627	0.050*
C19	1.1893 (9)	−0.2913 (7)	0.7336 (3)	0.0261 (16)
H19A	1.2676	−0.3201	0.7107	0.031*
H19B	1.1440	−0.2049	0.7171	0.031*
C20	1.0669 (8)	−0.4057 (7)	0.7300 (3)	0.0262 (16)
H20A	1.0250	−0.4197	0.6907	0.039*
H20B	0.9874	−0.3770	0.7517	0.039*
H20C	1.1112	−0.4923	0.7454	0.039*
N1	0.8788 (6)	0.3370 (5)	0.9937 (2)	0.0136 (11)
N2	1.0102 (6)	0.1260 (5)	0.9339 (2)	0.0158 (11)
N3	1.2599 (6)	−0.2626 (5)	0.7915 (2)	0.0193 (12)
Cl1	0.7217 (2)	0.37547 (19)	0.82157 (8)	0.0343 (5)
Cl2	0.61076 (19)	0.05105 (18)	0.93193 (7)	0.0275 (4)
Hg1	0.77787 (3)	0.23825 (3)	0.905699 (10)	0.01999 (11)
H10C	1.155 (5)	0.115 (8)	1.004 (3)	0.04 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.013 (2)	0.019 (2)	0.026 (3)	−0.0041 (18)	0.014 (2)	0.0005 (19)
C2	0.020 (4)	0.024 (4)	0.022 (4)	−0.006 (3)	−0.002 (3)	−0.001 (3)
C3	0.022 (4)	0.016 (3)	0.039 (4)	−0.007 (3)	0.008 (3)	−0.007 (3)
C4	0.019 (4)	0.024 (4)	0.025 (4)	−0.006 (3)	0.010 (3)	−0.002 (3)
C5	0.034 (4)	0.025 (4)	0.020 (4)	−0.011 (3)	0.000 (3)	−0.004 (3)
C6	0.028 (4)	0.013 (3)	0.025 (4)	−0.006 (3)	0.003 (3)	0.000 (3)
C7	0.021 (4)	0.018 (3)	0.024 (4)	−0.011 (3)	0.005 (3)	0.001 (3)
C8	0.017 (3)	0.028 (4)	0.012 (3)	−0.003 (3)	−0.006 (3)	0.002 (3)
C9	0.019 (4)	0.019 (3)	0.013 (3)	−0.010 (3)	0.001 (3)	0.001 (2)
C10	0.013 (2)	0.019 (2)	0.026 (3)	−0.0041 (18)	0.014 (2)	0.0005 (19)
C11	0.021 (4)	0.007 (3)	0.021 (3)	0.001 (3)	−0.002 (3)	−0.001 (2)
C12	0.024 (4)	0.013 (3)	0.022 (3)	−0.007 (3)	0.001 (3)	0.000 (3)
C13	0.018 (4)	0.014 (3)	0.036 (4)	0.003 (3)	−0.002 (3)	0.004 (3)
C14	0.021 (4)	0.022 (4)	0.017 (3)	−0.005 (3)	0.001 (3)	−0.001 (3)
C15	0.019 (3)	0.013 (3)	0.016 (3)	−0.003 (3)	−0.005 (3)	0.002 (2)
C16	0.020 (3)	0.014 (3)	0.022 (4)	0.005 (3)	−0.001 (3)	0.005 (3)
C17	0.022 (4)	0.015 (3)	0.033 (4)	0.004 (3)	0.003 (3)	−0.003 (3)
C18	0.022 (4)	0.024 (4)	0.054 (5)	0.006 (3)	0.006 (4)	0.008 (3)
C19	0.038 (4)	0.015 (3)	0.027 (4)	0.003 (3)	0.013 (3)	−0.001 (3)
C20	0.031 (4)	0.028 (4)	0.016 (3)	−0.004 (3)	−0.008 (3)	−0.004 (3)
N1	0.014 (3)	0.013 (3)	0.014 (3)	−0.008 (2)	0.002 (2)	−0.001 (2)
N2	0.013 (3)	0.016 (3)	0.018 (3)	0.002 (2)	0.002 (2)	0.002 (2)
N3	0.018 (3)	0.017 (3)	0.025 (3)	0.002 (2)	0.010 (2)	0.000 (2)
Cl1	0.0427 (12)	0.0243 (9)	0.0308 (10)	−0.0061 (8)	−0.0144 (8)	0.0075 (7)
Cl2	0.0202 (9)	0.0320 (9)	0.0285 (9)	−0.0071 (7)	−0.0035 (7)	0.0050 (7)
Hg1	0.01749 (17)	0.02169 (16)	0.02002 (16)	0.00000 (10)	−0.00049 (11)	−0.00019 (10)

Hg1—Cl1	2.3654 (19)	C14—C15	1.410 (9)
Hg1—Cl2	2.4394 (18)	C15—C16	1.383 (9)
Hg1—N1	2.340 (5)	C17—C18	1.499 (10)
Hg1—N2	2.334 (5)	C19—C20	1.527 (10)
N1—C1	1.363 (8)	C2—H2	0.9300
N1—C9	1.335 (8)	C3—H3	0.9300
N2—C10	1.290 (8)	C4—H4	0.9300
N2—C11	1.402 (8)	C5—H5	0.9300
N3—C14	1.358 (8)	C7—H7	0.9300
N3—C17	1.478 (9)	C8—H8	0.9300
N3—C19	1.448 (9)	C10—H10C	0.91 (6)
C1—C2	1.419 (10)	C12—H12	0.9300
C1—C6	1.418 (10)	C13—H13	0.9300
C2—C3	1.372 (10)	C15—H15	0.9300
C3—C4	1.392 (10)	C16—H16	0.9300
C4—C5	1.368 (10)	C17—H17A	0.9700
C5—C6	1.410 (10)	C17—H17B	0.9700
C6—C7	1.397 (10)	C18—H18A	0.9600
C7—C8	1.373 (9)	C18—H18B	0.9600
C8—C9	1.440 (10)	C18—H18C	0.9600
C9—C10	1.464 (9)	C19—H19A	0.9700
C11—C12	1.397 (9)	C19—H19B	0.9700
C11—C16	1.418 (10)	C20—H20A	0.9600
C12—C13	1.362 (9)	C20—H20B	0.9600
C13—C14	1.412 (10)	C20—H20C	0.9600
Cl1—Hg1—Cl2	122.85 (6)	C3—C2—H2	120.00
Cl1—Hg1—N1	122.31 (12)	C2—C3—H3	120.00
Cl1—Hg1—N2	124.75 (13)	C4—C3—H3	120.00
Cl2—Hg1—N1	103.99 (13)	C3—C4—H4	119.00
Cl2—Hg1—N2	97.92 (13)	C5—C4—H4	120.00
N1—Hg1—N2	73.11 (17)	C4—C5—H5	120.00
Hg1—N1—C1	128.9 (4)	C6—C5—H5	120.00
Hg1—N1—C9	111.2 (4)	C6—C7—H7	120.00
C1—N1—C9	119.4 (5)	C8—C7—H7	120.00
Hg1—N2—C10	113.9 (4)	C7—C8—H8	121.00
Hg1—N2—C11	124.4 (4)	C9—C8—H8	120.00
C10—N2—C11	121.5 (5)	N2—C10—H10C	125 (4)
C14—N3—C17	121.5 (5)	C9—C10—H10C	116 (5)
C14—N3—C19	122.6 (6)	C11—C12—H12	119.00
C17—N3—C19	115.9 (5)	C13—C12—H12	119.00
N1—C1—C2	118.9 (6)	C12—C13—H13	119.00
N1—C1—C6	121.9 (6)	C14—C13—H13	119.00
C2—C1—C6	119.1 (6)	C14—C15—H15	119.00
C1—C2—C3	120.4 (6)	C16—C15—H15	119.00
C2—C3—C4	120.1 (6)	C11—C16—H16	119.00
C3—C4—C5	121.0 (6)	C15—C16—H16	119.00
C4—C5—C6	120.7 (6)	N3—C17—H17A	109.00
C1—C6—C5	118.6 (6)	N3—C17—H17B	109.00
C1—C6—C7	118.3 (6)	C18—C17—H17A	109.00
C5—C6—C7	123.0 (6)	C18—C17—H17B	109.00
C6—C7—C8	119.9 (6)	H17A—C17—H17B	108.00
C7—C8—C9	119.1 (6)	C17—C18—H18A	110.00
N1—C9—C8	121.4 (6)	C17—C18—H18B	109.00
N1—C9—C10	120.9 (6)	C17—C18—H18C	109.00
C8—C9—C10	117.7 (6)	H18A—C18—H18B	109.00
N2—C10—C9	119.5 (6)	H18A—C18—H18C	109.00
N2—C11—C12	125.4 (6)	H18B—C18—H18C	109.00
N2—C11—C16	118.4 (6)	N3—C19—H19A	109.00
C12—C11—C16	116.2 (6)	N3—C19—H19B	109.00
C11—C12—C13	122.3 (6)	C20—C19—H19A	109.00
C12—C13—C14	122.2 (7)	C20—C19—H19B	109.00
N3—C14—C13	122.3 (6)	H19A—C19—H19B	108.00
N3—C14—C15	121.5 (6)	C19—C20—H20A	110.00
C13—C14—C15	116.2 (6)	C19—C20—H20B	109.00
C14—C15—C16	121.4 (6)	C19—C20—H20C	109.00
C11—C16—C15	121.7 (6)	H20A—C20—H20B	109.00
N3—C17—C18	114.4 (6)	H20A—C20—H20C	109.00
N3—C19—C20	113.7 (6)	H20B—C20—H20C	109.00
C1—C2—H2	120.00
C6—C1—C2—C3	−0 (1)	N2—C11—C16—C15	−179.8 (6)
N1—C1—C2—C3	−179.0 (6)	C12—C11—N2—C10	−6 (1)
C2—C1—C6—C5	2 (1)	C12—C11—N2—Hg1	178.5 (5)
C2—C1—C6—C7	−179.1 (6)	C16—C11—N2—C10	176.3 (6)
N1—C1—C6—C5	−179.6 (6)	C16—C11—N2—Hg1	1.1 (8)
N1—C1—C6—C7	−0 (1)	C11—C12—C13—C14	−0 (1)
C2—C1—N1—C9	177.2 (6)	C12—C13—C14—C15	1 (1)
C2—C1—N1—Hg1	−12.2 (9)	C12—C13—C14—N3	179.8 (6)
C6—C1—N1—C9	−1.7 (9)	C13—C14—C15—C16	−0 (1)
C6—C1—N1—Hg1	169.0 (5)	N3—C14—C15—C16	−179.0 (6)
C1—C2—C3—C4	−1 (1)	C13—C14—N3—C17	7 (1)
C2—C3—C4—C5	1 (1)	C13—C14—N3—C19	−174.1 (6)
C3—C4—C5—C6	1 (1)	C15—C14—N3—C17	−174.9 (6)
C4—C5—C6—C1	−2 (1)	C15—C14—N3—C19	5 (1)
C4—C5—C6—C7	178.9 (7)	C14—C15—C16—C11	−2 (1)
C1—C6—C7—C8	2 (1)	C18—C17—N3—C14	−86.3 (8)
C5—C6—C7—C8	−178.5 (7)	C18—C17—N3—C19	94.3 (7)
C6—C7—C8—C9	−2 (1)	C20—C19—N3—C14	−86.4 (8)
C7—C8—C9—C10	178.8 (6)	C20—C19—N3—C17	93.1 (7)
C7—C8—C9—N1	0 (1)	C1—N1—Hg1—N2	178.5 (6)
C8—C9—C10—N2	178.7 (6)	C1—N1—Hg1—Cl1	57.6 (5)
N1—C9—C10—N2	−3 (1)	C1—N1—Hg1—Cl2	−87.3 (5)
C8—C9—N1—C1	1.5 (9)	C9—N1—Hg1—N2	−10.3 (4)
C8—C9—N1—Hg1	−170.7 (5)	C9—N1—Hg1—Cl1	−131.1 (4)
C10—C9—N1—C1	−176.8 (6)	C9—N1—Hg1—Cl2	83.9 (4)
C10—C9—N1—Hg1	11.1 (7)	C10—N2—Hg1—N1	9.2 (4)
C9—C10—N2—C11	177.2 (6)	C10—N2—Hg1—Cl1	127.2 (4)
C9—C10—N2—Hg1	−7.1 (8)	C10—N2—Hg1—Cl2	−93.0 (4)
C16—C11—C12—C13	−2 (1)	C11—N2—Hg1—N1	−175.2 (5)
N2—C11—C12—C13	−179.2 (6)	C11—N2—Hg1—Cl1	−57.2 (5)
C12—C11—C16—C15	2 (1)	C11—N2—Hg1—Cl2	82.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl2i	0.93	2.82	3.703 (7)	159
C15—H15···Cl1ii	0.93	2.82	3.715 (7)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl2i	0.93	2.82	3.703 (7)	159
C15—H15⋯Cl1ii	0.93	2.82	3.715 (7)	162

Symmetry codes: (i) ; (ii) .