Bis(2,5-dimethyl­anilinium) tetra­chlorido­zincate(II)

Souissi, S.; Smirani, W.; Rzaigui, M.

doi:10.1107/S1600536809009982

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m442

doi:10.1107/S1600536809009982

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Bis(2,5-dimethylanilinium) tetrachloridozincate(II)

Sofiane Souissi,^a Wajda Smirani ^a ^* and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: wajda_sta@yahoo.fr

(Received 17 March 2009; accepted 18 March 2009; online 25 March 2009)

In the title compound, (C₈H₁₂N)₂[ZnCl₄], the Zn²⁺ ion adopts a distorted tetrahedral coordination geometry. In the crystal, the cations and anions are linked by N—H⋯Cl hydrogen bonds, leading to ribbons propagating parallel to the a axis.

Related literature

For related structures, see: Guo et al. (2007 ); Smirani & Rzaigui (2009 ). For background on hybrid materials, see: Tao et al. (2003 ); Bringley & Rajeswaran (2006 ).

Experimental

Crystal data

(C₈H₁₂N)₂[ZnCl₄]
M_r = 451.58
Monoclinic, P 2₁ /n
a = 7.425 (2) Å
b = 12.884 (2) Å
c = 22.809 (2) Å
β = 96.16 (2)°
V = 2169.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 293 K
0.20 × 0.13 × 0.10 mm

Data collection

Enraf–Nonius Turbo CAD-4 diffractometer
Absorption correction: none
6539 measured reflections
3947 independent reflections
2621 reflections with I > 2σ(I)
R_int = 0.033
2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.229
S = 1.05
3947 reflections
214 parameters
H-atom parameters not refined
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—Cl1	2.248 (2)
Zn1—Cl2	2.2502 (16)
Zn1—Cl3	2.274 (2)
Zn1—Cl4	2.2721 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl4ⁱ	0.89	2.25	3.125 (6)	169
N1—H1B⋯Cl3ⁱⁱ	0.89	2.54	3.304 (6)	145
N1—H1C⋯Cl2ⁱⁱⁱ	0.89	2.31	3.172 (7)	162
N2—H2A⋯Cl1ⁱ	0.89	2.34	3.219 (6)	171
N2—H2B⋯Cl4^iv	0.89	2.70	3.505 (7)	151
N2—H2C⋯Cl3ⁱⁱ	0.89	2.39	3.262 (6)	168
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z; (iv) x-1, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009982/hb2930sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009982/hb2930Isup2.hkl

checkCIF report

Comment top

Inorganic-organic hybrid materials are of great interest in solid state chemistry due to their enormous variety of intriguing structural topologies and their fascinating properties as well as great potential applications in many fields (Tao et al., 2003; Bringley & Rajeswaran, 2006). Here we report the crystal structure of bis(2,5-xylidinium) tetrachlorozincate (I).

As shown in Fig. 1, the asymmetric unit of (I) is built up from two 2,5-xylidinium cations and one tetrachlorozincate (II) anion. The Zn (II) ion is in a tetrahedral coordination environment composed of four Cl anions (Table 1). The Cl—Zn—Cl bond angles range from 106.13 (8) to 112.46 (8)°. These values indicate that the anionic [ZnCl₄]^2- tetrahedron is slightly distorted (Guo et al., 2007). The examination of the organic cation shows that the values of the N—C, C—C distances and N—C—C, C—C—C angles range from 1.343 (12) to 1.512 (11) Å and 115.90 (7) to 123.0 (6)°, respectively. These values show no significant difference from those obtained in other crystals involving the same organic groups (Smirani and Rzaigui, 2009).

A projection of the structure along the direction a shows that the [ZnCl₄]^2- anions are connected via N—H···Cl hydrogen bonds originating from NH₃⁺ groups, so as to built inorganic ribbons at x = 0 and x = 1/2 (Fig. 2, Table 2). The 2,5-xylidinium cations are anchored onto the successive ribbons via hydrogen bonds and electrostatic and van der Waals interactions, to compensate their negative charges.

Related literature top

For related structures, see: Guo et al. (2007); Smirani & Rzaigui (2009). For background on hybrid materials, see: Tao et al. (2003); Bringley & Rajeswaran (2006).

Experimental top

An aqueous solution of 2,5-xylidine, HCl and ZnCl₂ in a 2:2:1 molar ratio was prepared and colourless blocks of (I) grew as the water evaporated over the course of a few days.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the molecular structure of (I): displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. A view of the packing in (I) viewed along the a axis.

Bis(2,5-dimethylanilinium) tetrachloridozincate(II) top

Crystal data top

(C₈H₁₂N)₂[ZnCl₄]	F(000) = 928
M_r = 451.58	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.425 (2) Å	θ = 9.9–11.0°
b = 12.884 (2) Å	µ = 1.62 mm⁻¹
c = 22.809 (2) Å	T = 293 K
β = 96.16 (2)°	Block, colourless
V = 2169.5 (7) Å³	0.20 × 0.13 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius Turbo CAD-4 diffractometer	θ_max = 28.0°, θ_min = 2.4°
Radiation source: Enraf Nonius FR590	h = −9→9
Nonprofiled ω scans	k = 0→17
6539 measured reflections	l = −10→17
3947 independent reflections	2 standard reflections every 120 min
2621 reflections with I > 2σ(I)	intensity decay: 5%
R_int = 0.033

Refinement top

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters not refined
S = 1.05	w = 1/[σ²(F_o²) + (0.1531P)²] where P = (F_o² + 2F_c²)/3
3947 reflections	(Δ/σ)_max = 0.012
214 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

(C₈H₁₂N)₂[ZnCl₄]	V = 2169.5 (7) Å³
M_r = 451.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.425 (2) Å	µ = 1.62 mm⁻¹
b = 12.884 (2) Å	T = 293 K
c = 22.809 (2) Å	0.20 × 0.13 × 0.10 mm
β = 96.16 (2)°

Data collection top

Enraf–Nonius Turbo CAD-4 diffractometer	R_int = 0.033
6539 measured reflections	2 standard reflections every 120 min
3947 independent reflections	intensity decay: 5%
2621 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.229	H-atom parameters not refined
S = 1.05	Δρ_max = 0.50 e Å⁻³
3947 reflections	Δρ_min = −0.61 e Å⁻³
214 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.0360 (2)	0.16857 (16)	0.12060 (10)	0.0688 (6)
Cl2	0.52806 (19)	0.20922 (13)	0.10654 (9)	0.0537 (5)
Cl3	0.1904 (2)	0.22519 (13)	−0.02438 (9)	0.0583 (6)
Cl4	0.3103 (3)	−0.02537 (13)	0.04807 (11)	0.0808 (7)
N1	0.2378 (7)	0.7499 (4)	−0.0004 (3)	0.0562 (16)
H1A	0.2629	0.8096	0.0183	0.084*
H1B	0.1189	0.7451	−0.0105	0.084*
H1C	0.2950	0.7474	−0.0328	0.084*
C1	0.2981 (7)	0.6631 (4)	0.0386 (3)	0.0414 (17)
C3	0.3769 (8)	0.6844 (4)	0.0940 (3)	0.0490 (19)
H3	0.3922	0.7531	0.1061	0.059*
C4	0.4345 (8)	0.6053 (5)	0.1327 (3)	0.0527 (18)
C2	0.2704 (7)	0.5621 (4)	0.0171 (3)	0.0407 (16)
C5	0.3295 (8)	0.4834 (4)	0.0569 (3)	0.0513 (19)
H5	0.3153	0.4146	0.0451	0.062*
C9	0.1839 (10)	0.5398 (6)	−0.0438 (3)	0.062 (2)
H9A	0.0653	0.5703	−0.0490	0.093*
H9B	0.1742	0.4661	−0.0495	0.093*
H9C	0.2567	0.5686	−0.0721	0.093*
C8	0.4080 (9)	0.5049 (5)	0.1130 (4)	0.0530 (19)
H8	0.4441	0.4502	0.1382	0.064*
C7	0.5214 (14)	0.6282 (7)	0.1943 (4)	0.086 (3)
H7A	0.6431	0.6522	0.1925	0.129*
H7B	0.5235	0.5661	0.2177	0.129*
H7C	0.4529	0.6808	0.2119	0.129*
N2	−0.2368 (8)	0.9737 (4)	0.1100 (3)	0.0565 (17)
H2A	−0.1525	1.0231	0.1114	0.085*
H2B	−0.3429	0.9999	0.0952	0.085*
H2C	−0.2061	0.9220	0.0872	0.085*
C10	−0.2512 (9)	0.9346 (4)	0.1696 (3)	0.0456 (17)
C13	−0.1163 (9)	0.8706 (5)	0.1964 (3)	0.0483 (19)
C11	−0.3993 (9)	0.9637 (6)	0.1974 (4)	0.062 (2)
H11	−0.4863	1.0074	0.1782	0.075*
C14	0.0465 (11)	0.8399 (7)	0.1675 (4)	0.082 (3)
H14A	0.0186	0.7799	0.1433	0.123*
H14B	0.1443	0.8240	0.1971	0.123*
H14C	0.0813	0.8961	0.1434	0.123*
C12	−0.4195 (10)	0.9281 (7)	0.2541 (4)	0.065 (2)
C16	−0.2860 (11)	0.8619 (6)	0.2797 (4)	0.062 (2)
H16	−0.2972	0.8346	0.3169	0.075*
C15	−0.1412 (11)	0.8360 (6)	0.2523 (4)	0.062 (2)
H15	−0.0538	0.7929	0.2718	0.075*
C17	−0.5803 (14)	0.9593 (10)	0.2849 (5)	0.120 (4)
H17A	−0.6893	0.9349	0.2627	0.180*
H17B	−0.5844	1.0335	0.2879	0.180*
H17C	−0.5701	0.9293	0.3236	0.180*
Zn1	0.26302 (8)	0.14604 (5)	0.06412 (4)	0.0418 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0506 (9)	0.0874 (13)	0.0709 (18)	0.0007 (8)	0.0174 (9)	−0.0083 (11)
Cl2	0.0423 (7)	0.0579 (9)	0.0584 (15)	−0.0086 (6)	−0.0064 (7)	−0.0055 (8)
Cl3	0.0709 (10)	0.0511 (9)	0.0506 (16)	−0.0023 (7)	−0.0040 (9)	0.0047 (8)
Cl4	0.1136 (16)	0.0354 (8)	0.0909 (19)	−0.0001 (9)	−0.0004 (13)	−0.0092 (9)
N1	0.067 (3)	0.039 (3)	0.063 (5)	0.003 (2)	0.004 (3)	0.008 (3)
C1	0.036 (3)	0.033 (3)	0.056 (6)	0.003 (2)	0.012 (3)	0.003 (3)
C3	0.047 (3)	0.036 (3)	0.063 (6)	0.000 (2)	0.001 (3)	−0.004 (3)
C4	0.048 (3)	0.052 (3)	0.057 (6)	−0.001 (3)	−0.001 (3)	0.004 (3)
C2	0.037 (3)	0.041 (3)	0.046 (5)	−0.004 (2)	0.012 (3)	−0.001 (3)
C5	0.047 (3)	0.033 (3)	0.076 (6)	−0.001 (2)	0.011 (3)	0.005 (3)
C9	0.066 (4)	0.056 (4)	0.064 (7)	−0.008 (3)	0.006 (4)	−0.012 (4)
C8	0.053 (3)	0.042 (3)	0.063 (6)	0.005 (3)	0.000 (4)	0.008 (3)
C7	0.101 (7)	0.075 (5)	0.077 (8)	−0.001 (5)	−0.014 (6)	0.001 (5)
N2	0.075 (4)	0.054 (3)	0.041 (5)	0.004 (3)	0.005 (3)	0.008 (3)
C10	0.060 (4)	0.047 (3)	0.029 (5)	−0.006 (3)	0.000 (3)	0.001 (3)
C13	0.057 (4)	0.053 (3)	0.033 (6)	−0.003 (3)	−0.004 (3)	0.001 (3)
C11	0.058 (4)	0.069 (4)	0.058 (7)	0.013 (3)	−0.003 (4)	0.000 (4)
C14	0.068 (5)	0.109 (7)	0.067 (8)	0.026 (5)	0.002 (5)	−0.002 (5)
C12	0.067 (4)	0.087 (5)	0.042 (7)	−0.006 (4)	0.012 (4)	−0.002 (4)
C16	0.075 (5)	0.076 (5)	0.034 (6)	−0.009 (4)	−0.001 (4)	0.009 (4)
C15	0.068 (5)	0.065 (4)	0.051 (7)	0.006 (3)	−0.008 (4)	0.007 (4)
C17	0.085 (6)	0.195 (13)	0.082 (9)	0.028 (7)	0.020 (6)	−0.011 (8)
Zn1	0.0383 (4)	0.0382 (4)	0.0481 (8)	−0.0011 (3)	0.0007 (3)	−0.0031 (3)

Geometric parameters (Å, º) top

Zn1—Cl1	2.248 (2)	C7—H7B	0.9600
Zn1—Cl2	2.2502 (16)	C7—H7C	0.9600
Zn1—Cl3	2.274 (2)	N2—C10	1.463 (9)
Zn1—Cl4	2.2721 (18)	N2—H2A	0.8900
N1—C1	1.468 (8)	N2—H2B	0.8900
N1—H1A	0.8900	N2—H2C	0.8900
N1—H1B	0.8900	C10—C11	1.379 (10)
N1—H1C	0.8900	C10—C13	1.388 (9)
C1—C3	1.364 (10)	C13—C15	1.382 (11)
C1—C2	1.399 (8)	C13—C14	1.491 (11)
C3—C4	1.386 (9)	C11—C12	1.396 (11)
C3—H3	0.9300	C11—H11	0.9300
C4—C8	1.377 (9)	C14—H14A	0.9600
C4—C7	1.512 (11)	C14—H14B	0.9600
C2—C5	1.400 (9)	C14—H14C	0.9600
C2—C9	1.495 (10)	C12—C16	1.388 (11)
C5—C8	1.376 (10)	C12—C17	1.503 (13)
C5—H5	0.9300	C16—C15	1.343 (12)
C9—H9A	0.9600	C16—H16	0.9300
C9—H9B	0.9600	C15—H15	0.9300
C9—H9C	0.9600	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C7—H7A	0.9600	C17—H17C	0.9600

C1—N1—H1A	109.5	C10—N2—H2C	109.5
C1—N1—H1B	109.5	H2A—N2—H2C	109.5
H1A—N1—H1B	109.5	H2B—N2—H2C	109.5
C1—N1—H1C	109.5	C11—C10—C13	122.2 (7)
H1A—N1—H1C	109.5	C11—C10—N2	118.4 (6)
H1B—N1—H1C	109.5	C13—C10—N2	119.5 (6)
C3—C1—C2	123.0 (6)	C15—C13—C10	115.9 (7)
C3—C1—N1	118.8 (5)	C15—C13—C14	121.2 (7)
C2—C1—N1	118.2 (6)	C10—C13—C14	122.9 (7)
C1—C3—C4	121.0 (6)	C10—C11—C12	120.5 (7)
C1—C3—H3	119.5	C10—C11—H11	119.8
C4—C3—H3	119.5	C12—C11—H11	119.8
C8—C4—C3	117.4 (7)	C13—C14—H14A	109.5
C8—C4—C7	121.2 (7)	C13—C14—H14B	109.5
C3—C4—C7	121.3 (7)	H14A—C14—H14B	109.5
C1—C2—C5	115.0 (6)	C13—C14—H14C	109.5
C1—C2—C9	122.5 (6)	H14A—C14—H14C	109.5
C5—C2—C9	122.5 (6)	H14B—C14—H14C	109.5
C8—C5—C2	122.0 (6)	C16—C12—C11	116.7 (7)
C8—C5—H5	119.0	C16—C12—C17	122.3 (9)
C2—C5—H5	119.0	C11—C12—C17	121.0 (8)
C2—C9—H9A	109.5	C15—C16—C12	121.8 (8)
C2—C9—H9B	109.5	C15—C16—H16	119.1
H9A—C9—H9B	109.5	C12—C16—H16	119.1
C2—C9—H9C	109.5	C16—C15—C13	122.9 (7)
H9A—C9—H9C	109.5	C16—C15—H15	118.5
H9B—C9—H9C	109.5	C13—C15—H15	118.5
C5—C8—C4	121.6 (6)	C12—C17—H17A	109.5
C5—C8—H8	119.2	C12—C17—H17B	109.5
C4—C8—H8	119.2	H17A—C17—H17B	109.5
C4—C7—H7A	109.5	C12—C17—H17C	109.5
C4—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
C4—C7—H7C	109.5	Cl1—Zn1—Cl2	112.46 (8)
H7A—C7—H7C	109.5	Cl1—Zn1—Cl4	110.87 (9)
H7B—C7—H7C	109.5	Cl2—Zn1—Cl4	106.13 (8)
C10—N2—H2A	109.5	Cl1—Zn1—Cl3	109.26 (8)
C10—N2—H2B	109.5	Cl2—Zn1—Cl3	109.42 (7)
H2A—N2—H2B	109.5	Cl4—Zn1—Cl3	108.59 (9)

C2—C1—C3—C4	−0.1 (9)	C11—C10—C13—C15	1.3 (10)
N1—C1—C3—C4	179.4 (6)	N2—C10—C13—C15	−179.2 (6)
C1—C3—C4—C8	−0.4 (10)	C11—C10—C13—C14	−178.8 (7)
C1—C3—C4—C7	−179.8 (7)	N2—C10—C13—C14	0.7 (10)
C3—C1—C2—C5	0.1 (8)	C13—C10—C11—C12	−0.7 (11)
N1—C1—C2—C5	−179.3 (5)	N2—C10—C11—C12	179.7 (6)
C3—C1—C2—C9	−180.0 (6)	C10—C11—C12—C16	−1.0 (11)
N1—C1—C2—C9	0.6 (9)	C10—C11—C12—C17	180.0 (9)
C1—C2—C5—C8	0.3 (9)	C11—C12—C16—C15	2.2 (12)
C9—C2—C5—C8	−179.6 (6)	C17—C12—C16—C15	−178.7 (9)
C2—C5—C8—C4	−0.8 (10)	C12—C16—C15—C13	−1.8 (12)
C3—C4—C8—C5	0.8 (10)	C10—C13—C15—C16	0.0 (11)
C7—C4—C8—C5	−179.8 (7)	C14—C13—C15—C16	−179.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4ⁱ	0.89	2.25	3.125 (6)	169
N1—H1B···Cl3ⁱⁱ	0.89	2.54	3.304 (6)	145
N1—H1C···Cl2ⁱⁱⁱ	0.89	2.31	3.172 (7)	162
N2—H2A···Cl1ⁱ	0.89	2.34	3.219 (6)	171
N2—H2B···Cl4^iv	0.89	2.70	3.505 (7)	151
N2—H2C···Cl3ⁱⁱ	0.89	2.39	3.262 (6)	168

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₈H₁₂N)₂[ZnCl₄]
M_r	451.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.425 (2), 12.884 (2), 22.809 (2)
β (°)	96.16 (2)
V (Å³)	2169.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.20 × 0.13 × 0.10

Data collection
Diffractometer	Enraf–Nonius Turbo CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6539, 3947, 2621
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.229, 1.05
No. of reflections	3947
No. of parameters	214
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.61

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Zn1—Cl1	2.248 (2)	Zn1—Cl3	2.274 (2)
Zn1—Cl2	2.2502 (16)	Zn1—Cl4	2.2721 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4ⁱ	0.89	2.25	3.125 (6)	169
N1—H1B···Cl3ⁱⁱ	0.89	2.54	3.304 (6)	145
N1—H1C···Cl2ⁱⁱⁱ	0.89	2.31	3.172 (7)	162
N2—H2A···Cl1ⁱ	0.89	2.34	3.219 (6)	171
N2—H2B···Cl4^iv	0.89	2.70	3.505 (7)	151
N2—H2C···Cl3ⁱⁱ	0.89	2.39	3.262 (6)	168

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x−1, y+1, z.

References

Bringley, J. F. & Rajeswaran, M. (2006). Acta Cryst. E62, m1304–m1305. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Guo, N., Yi, J., Chen, Y., Liao, S. & Fu, Z. (2007). Acta Cryst. E63, m2571. Web of Science CSD CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smirani, W. & Rzaigui, M. (2009). Acta Cryst. E65, o83. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tao, J., Yin, X., Jiang, Y. B., Yang, L. F., Huang, R. B. & Zheng, L. S. (2003). Eur. J. Inorg. Chem. pp. 2678–2682. Web of Science CSD CrossRef Google Scholar

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Volume 65| Part 4| April 2009| Page m442

doi:10.1107/S1600536809009982

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