Dichloridobis(isoquinoline-κN)zinc(II).

In the title compound, [ZnCl(2)(C(9)H(7)N)(2)], the Zn(II) cation is coordinated by two Cl(-) anions and two isoquinoline ligands in a distorted ZnCl(2)N(2) tetra-hedral geometry; the two isoquinoline ring systems are twisted with respect to each other at a dihedral angle of 45.72 (8)°. The parallel isoqiunoline ring systems of adjacent mol-ecules are partially overlapped, with the shorter face-to-face distance of 3.438 (19) Å indicating the existence of weak π-π stacking in the crystal structure.

Related literature

For general background to π-π stacking, see: Deisenhofer & Michel (1989 ▶); Su & Xu (2004 ▶); Xu et al. (2007 ▶). For π-π stacking between isoquinoline ring systems in a CoII complex, see: Li et al. (2010 ▶).

Experimental

Crystal data

[ZnCl2(C9H7N)2]

M = 394.58

Monoclinic,

a = 7.8956 (15) Å

b = 13.363 (2) Å

c = 15.677 (2) Å

β = 90.220 (8)°

V = 1654.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.81 mm−1

T = 294 K

0.40 × 0.32 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.788, T max = 0.862

11270 measured reflections

2975 independent reflections

1933 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.153

S = 0.95

2975 reflections

208 parameters

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −0.39 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024803/hb5517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024803/hb5517Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl2(C9H7N)2]	F(000) = 800
Mr = 394.58	Dx = 1.585 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6266 reflections
a = 7.8956 (15) Å	θ = 3.3–24.6°
b = 13.363 (2) Å	µ = 1.81 mm−1
c = 15.677 (2) Å	T = 294 K
β = 90.220 (8)°	Prism, colorless
V = 1654.0 (5) Å3	0.40 × 0.32 × 0.30 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2975 independent reflections
Radiation source: fine-focus sealed tube	1933 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→15
Tmin = 0.788, Tmax = 0.862	l = −18→17
11270 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.1036P)2] where P = (Fo2 + 2Fc2)/3
2975 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 1.33 e Å−3
0 restraints	Δρmin = −0.39 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
Zn	0.75125 (6)	0.30754 (4)	0.25278 (3)	0.0408 (2)
Cl1	0.51169 (15)	0.22275 (10)	0.27066 (8)	0.0597 (4)
Cl2	0.98654 (16)	0.21580 (10)	0.25609 (9)	0.0616 (4)
N1	0.7603 (4)	0.3828 (3)	0.1381 (2)	0.0448 (9)
N2	0.7615 (5)	0.4115 (3)	0.3490 (2)	0.0466 (9)
C1	0.7034 (6)	0.4723 (4)	0.1236 (3)	0.0482 (11)
H1	0.6550	0.5071	0.1688	0.058*
C2	0.7109 (5)	0.5212 (3)	0.0418 (3)	0.0423 (10)
C3	0.6513 (6)	0.6175 (4)	0.0286 (3)	0.0590 (13)
H3	0.6042	0.6540	0.0731	0.071*
C4	0.6632 (7)	0.6570 (4)	−0.0501 (3)	0.0651 (14)
H4	0.6234	0.7216	−0.0595	0.078*
C5	0.7340 (7)	0.6037 (5)	−0.1187 (3)	0.0645 (15)
H5	0.7409	0.6337	−0.1721	0.077*
C6	0.7913 (7)	0.5106 (5)	−0.1080 (3)	0.0620 (14)
H6	0.8365	0.4755	−0.1538	0.074*
C7	0.7822 (6)	0.4647 (4)	−0.0243 (3)	0.0481 (12)
C8	0.8407 (6)	0.3682 (4)	−0.0097 (3)	0.0589 (13)
H8	0.8863	0.3301	−0.0536	0.071*
C9	0.8294 (6)	0.3310 (4)	0.0713 (3)	0.0559 (12)
H9	0.8708	0.2670	0.0816	0.067*
C10	0.7032 (6)	0.3890 (4)	0.4234 (3)	0.0525 (12)
H10	0.6485	0.3279	0.4303	0.063*
C11	0.7191 (5)	0.4547 (3)	0.4968 (3)	0.0444 (11)
C12	0.6585 (7)	0.4275 (4)	0.5760 (3)	0.0620 (14)
H12	0.6066	0.3658	0.5846	0.074*
C13	0.6774 (7)	0.4941 (5)	0.6412 (3)	0.0676 (15)
H13	0.6375	0.4770	0.6950	0.081*
C14	0.7542 (6)	0.5864 (4)	0.6299 (3)	0.0591 (14)
H14	0.7638	0.6297	0.6761	0.071*
C15	0.8152 (6)	0.6148 (4)	0.5537 (3)	0.0582 (13)
H15	0.8673	0.6767	0.5473	0.070*
C16	0.7987 (5)	0.5473 (3)	0.4815 (3)	0.0448 (11)
C17	0.8591 (6)	0.5706 (4)	0.4020 (3)	0.0552 (13)
H17	0.9120	0.6316	0.3920	0.066*
C18	0.8402 (6)	0.5027 (4)	0.3381 (3)	0.0551 (13)
H18	0.8824	0.5185	0.2845	0.066*

	U11	U22	U33	U12	U13	U23
Zn	0.0544 (4)	0.0332 (3)	0.0347 (3)	0.0000 (2)	0.0035 (2)	−0.0002 (2)
Cl1	0.0625 (8)	0.0496 (8)	0.0672 (8)	−0.0098 (6)	0.0145 (6)	−0.0045 (6)
Cl2	0.0638 (8)	0.0546 (8)	0.0665 (8)	0.0131 (6)	0.0068 (6)	−0.0011 (6)
N1	0.051 (2)	0.042 (2)	0.042 (2)	−0.0036 (18)	−0.0006 (16)	0.0036 (17)
N2	0.053 (2)	0.049 (2)	0.037 (2)	0.0060 (19)	0.0019 (16)	−0.0027 (18)
C1	0.053 (3)	0.048 (3)	0.043 (3)	−0.004 (2)	−0.002 (2)	−0.006 (2)
C2	0.047 (2)	0.043 (3)	0.037 (2)	−0.007 (2)	−0.0001 (19)	−0.007 (2)
C3	0.072 (3)	0.050 (3)	0.055 (3)	0.004 (3)	−0.007 (2)	−0.003 (3)
C4	0.073 (3)	0.070 (4)	0.053 (3)	−0.011 (3)	−0.010 (3)	0.012 (3)
C5	0.077 (4)	0.082 (4)	0.034 (3)	−0.015 (3)	−0.003 (2)	0.018 (3)
C6	0.071 (3)	0.074 (4)	0.040 (3)	−0.006 (3)	0.002 (2)	0.009 (3)
C7	0.048 (3)	0.046 (3)	0.050 (3)	−0.006 (2)	−0.002 (2)	−0.005 (2)
C8	0.071 (3)	0.060 (3)	0.045 (3)	0.004 (3)	0.008 (2)	−0.015 (2)
C9	0.071 (3)	0.056 (3)	0.041 (3)	0.000 (3)	0.009 (2)	−0.002 (2)
C10	0.054 (3)	0.057 (3)	0.046 (3)	0.001 (2)	0.000 (2)	0.001 (2)
C11	0.041 (2)	0.044 (3)	0.049 (3)	0.005 (2)	0.001 (2)	0.005 (2)
C12	0.067 (3)	0.061 (4)	0.058 (3)	−0.002 (3)	0.010 (3)	0.008 (3)
C13	0.075 (4)	0.078 (4)	0.049 (3)	0.005 (3)	−0.001 (3)	−0.012 (3)
C14	0.069 (3)	0.067 (4)	0.041 (3)	0.011 (3)	−0.004 (2)	−0.013 (3)
C15	0.062 (3)	0.063 (3)	0.050 (3)	0.008 (3)	−0.005 (2)	−0.008 (3)
C16	0.042 (2)	0.049 (3)	0.043 (3)	0.013 (2)	0.0004 (19)	0.012 (2)
C17	0.072 (3)	0.038 (3)	0.056 (3)	−0.003 (2)	0.004 (2)	0.010 (2)
C18	0.073 (3)	0.043 (3)	0.050 (3)	0.002 (2)	−0.005 (2)	−0.007 (2)

Zn—N1	2.062 (4)	C7—C8	1.388 (7)
Zn—N2	2.052 (4)	C8—C9	1.366 (7)
Zn—Cl1	2.2235 (13)	C8—H8	0.9300
Zn—Cl2	2.2262 (13)	C9—H9	0.9300
N1—C1	1.298 (6)	C10—C11	1.453 (6)
N1—C9	1.370 (6)	C10—H10	0.9300
N2—C10	1.290 (6)	C11—C12	1.381 (7)
N2—C18	1.379 (6)	C11—C16	1.409 (6)
C1—C2	1.441 (6)	C12—C13	1.363 (7)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.385 (7)	C13—C14	1.387 (8)
C2—C7	1.403 (6)	C13—H13	0.9300
C3—C4	1.346 (7)	C14—C15	1.344 (7)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.406 (8)	C15—C16	1.453 (7)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.334 (8)	C16—C17	1.371 (6)
C5—H5	0.9300	C17—C18	1.359 (7)
C6—C7	1.450 (7)	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
N2—Zn—N1	108.05 (16)	C9—C8—C7	117.9 (5)
N2—Zn—Cl1	106.47 (11)	C9—C8—H8	121.0
N1—Zn—Cl1	112.99 (10)	C7—C8—H8	121.0
N2—Zn—Cl2	108.96 (11)	C8—C9—N1	123.6 (5)
N1—Zn—Cl2	104.91 (11)	C8—C9—H9	118.2
Cl1—Zn—Cl2	115.26 (6)	N1—C9—H9	118.2
C1—N1—C9	118.1 (4)	N2—C10—C11	123.0 (5)
C1—N1—Zn	126.1 (3)	N2—C10—H10	118.5
C9—N1—Zn	115.8 (3)	C11—C10—H10	118.5
C10—N2—C18	118.7 (4)	C12—C11—C16	122.8 (5)
C10—N2—Zn	119.6 (4)	C12—C11—C10	121.6 (5)
C18—N2—Zn	121.6 (3)	C16—C11—C10	115.6 (4)
N1—C1—C2	123.9 (4)	C13—C12—C11	117.7 (5)
N1—C1—H1	118.1	C13—C12—H12	121.2
C2—C1—H1	118.1	C11—C12—H12	121.2
C3—C2—C7	121.8 (4)	C12—C13—C14	122.1 (5)
C3—C2—C1	122.6 (4)	C12—C13—H13	118.9
C7—C2—C1	115.6 (4)	C14—C13—H13	118.9
C4—C3—C2	118.4 (5)	C15—C14—C13	121.5 (5)
C4—C3—H3	120.8	C15—C14—H14	119.2
C2—C3—H3	120.8	C13—C14—H14	119.2
C3—C4—C5	122.1 (5)	C14—C15—C16	119.1 (5)
C3—C4—H4	118.9	C14—C15—H15	120.5
C5—C4—H4	118.9	C16—C15—H15	120.5
C6—C5—C4	120.8 (5)	C17—C16—C11	120.7 (5)
C6—C5—H5	119.6	C17—C16—C15	122.5 (5)
C4—C5—H5	119.6	C11—C16—C15	116.8 (4)
C5—C6—C7	119.3 (5)	C18—C17—C16	118.7 (5)
C5—C6—H6	120.3	C18—C17—H17	120.6
C7—C6—H6	120.3	C16—C17—H17	120.6
C8—C7—C2	120.8 (4)	C17—C18—N2	123.2 (5)
C8—C7—C6	121.7 (5)	C17—C18—H18	118.4
C2—C7—C6	117.5 (5)	N2—C18—H18	118.4

Table 1

Selected bond lengths (Å)

Zn—N1	2.062 (4)
Zn—N2	2.052 (4)
Zn—Cl1	2.2235 (13)
Zn—Cl2	2.2262 (13)