Dichloridobis[2-(1-hydrazinylideneeth­yl)pyrazine-κN1]zinc

Liang, L.; Li, M.; Liu, J.; Wei, Y.

doi:10.1107/S1600536812016418

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m710

doi:10.1107/S1600536812016418

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Dichloridobis[2-(1-hydrazinylideneethyl)pyrazine-κN¹]zinc

Li-li Liang,^a Meng Li,^a ^* Jia-cheng Liu ^a and Yun Wei ^a

^aCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: jcliu8@nwnu.edu.cn

(Received 30 March 2012; accepted 16 April 2012; online 28 April 2012)

In the structure of the title complex, [ZnCl₂(C₆H₈N₄)₂], the Zn^II atom has a distorted octahedral geometry. Two cis Cl⁻ ions and four N atoms belonging to two different 2-(1-hydrazinylideneethyl)pyrazine ligands coordinate the Zn^II atom, forming two five-membered Zn—N—C—C—N rings. The dihedral angle between the planes of these metallocycles is 88.13 (4)°. The organic ligands are essentially planar (r.m.s. deviations from planarity = 0.072 and 0.040 Å). Intermolecular N—H⋯N and N—H⋯Cl interactions join the molecules into a three-dimensional framework.

Related literature

For the biochemical applications of complexes based on ligands containing pyrazine, see: Ha et al. (1999 ); Blackstock et al. (2000 ); Adams et al. (2002 ); Lee et al. (2012 ). For the preparation of the ligand, see: Stadler et al. (2010 ).

Experimental

Crystal data

[ZnCl₂(C₆H₈N₄)₂]
M_r = 408.60
Monoclinic, P 2₁ /n
a = 8.4289 (8) Å
b = 15.1128 (14) Å
c = 13.4196 (13) Å
β = 104.077 (1)°
V = 1658.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.81 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.713, T_max = 0.773
11576 measured reflections
4132 independent reflections
3456 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.03
4132 reflections
223 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H2N8⋯Cl1	0.86 (2)	2.73 (2)	3.400 (2)	137 (2)
N8—H2N8⋯N1ⁱ	0.86 (2)	2.60 (2)	3.165 (3)	124 (2)
N4—H2N4⋯Cl2	0.83 (2)	2.60 (2)	3.250 (2)	137 (2)
N4—H1N4⋯Cl1ⁱⁱ	0.81 (2)	2.66 (2)	3.4429 (19)	165 (2)
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016418/pk2404sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016418/pk2404Isup2.hkl

checkCIF report

Comment top

Pyrazine and its derivatives have received considerable attention and interest in the field of biochemistry. Such research has been focused on drugs (Ha et al., 1999; Blackstock et al., 2000), flavor ingredients (Adams et al., 2002), and enzymatic modification (Lee et al., 2012). In this paper, a new Zn^II complex, dicholorido-bis[2-(1-hydrazonethyl) pyrazine]zinc(II), is described.

The crystal of the title compound, [ZnCl₂(C₆H₈N₄)₂], consists of two Cl^- ions, two N atoms from two different pyrazines (N2, N6) and other two imine N atoms (N3, N7), forming a distorted octahedron (Fig. 1). The equatorial plane of the octahedron is occupied by Cl1, N2, N6 and Cl2, the four atoms are almost coplanar, with the dihedral angle of 13.28 (1)°. Atoms N3, N7 are in the axial positions of the octahedron. The distances between N3, N7 and Zn^II (2.158 (1) Å, 2.164 (1) Å) are shorter than those of N2, N6 of the equatorial plane with Zn^II (2.244 (1) Å, 2.258 (2) Å).

As shown in the packing diagram (Fig. 2), a three-dimensional framework is formed by intermolecular N—H···N and N—H···Cl interactions.

Related literature top

For the biochemical applications of complexes based on ligands containing pyrazine, see: Ha et al. (1999); Blackstock et al. (2000); Adams et al. (2002); Lee et al. (2012). For the preparation of the ligand, see: Stadler et al. (2010).

Experimental top

2-(1-hydrazinylideneethyl)pyrazine (Stadler et al., 2010) (0.1 mmol, 0.0136 g) was dissolved in 20 ml absolute ethanol, then ZnCl₂.2H₂O (0.2 mmol, 0.0268 g) was added, and after 0.5 h of stirring at 333 K, the mixture was filtered and held at room temperature to allow slow evaporation of solvent. Shiny pale yellow crystals suitable for X-ray diffraction were collected after one week (Yield = 64%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The crystal structure of the title complex. Ellipsoids are drawn at the 50% probability level. Hydrogen atoms are depicted as small spheres of arbitrary radius.
	Fig. 2. The packing diagram of the title complex, viewed along the a axis. Intermolecular interactions are shown as dashed lines.

Dichloridobis[2-(1-hydrazinylideneethyl)pyrazine-κN¹]zinc top

Crystal data top

[ZnCl₂(C₆H₈N₄)₂]	F(000) = 832
M_r = 408.60	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4411 reflections
a = 8.4289 (8) Å	θ = 2.7–28.2°
b = 15.1128 (14) Å	µ = 1.81 mm⁻¹
c = 13.4196 (13) Å	T = 296 K
β = 104.077 (1)°	Block, colourless
V = 1658.1 (3) Å³	0.20 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4132 independent reflections
Radiation source: fine-focus sealed tube	3456 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→11
T_min = 0.713, T_max = 0.773	k = −18→20
11576 measured reflections	l = −9→17

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.042P)² + 0.3057P] where P = (F_o² + 2F_c²)/3
4132 reflections	(Δ/σ)_max = 0.009
223 parameters	Δρ_max = 0.42 e Å⁻³
4 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[ZnCl₂(C₆H₈N₄)₂]	V = 1658.1 (3) Å³
M_r = 408.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4289 (8) Å	µ = 1.81 mm⁻¹
b = 15.1128 (14) Å	T = 296 K
c = 13.4196 (13) Å	0.20 × 0.18 × 0.15 mm
β = 104.077 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4132 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3456 reflections with I > 2σ(I)
T_min = 0.713, T_max = 0.773	R_int = 0.026
11576 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	4 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.42 e Å⁻³
4132 reflections	Δρ_min = −0.21 e Å⁻³
223 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
Zn1	0.79801 (2)	0.074400 (13)	0.764996 (15)	0.03098 (8)
Cl1	0.74457 (6)	0.17192 (3)	0.89354 (4)	0.04074 (12)
Cl2	0.61902 (6)	−0.03984 (4)	0.78802 (4)	0.04526 (13)
N1	1.2922 (2)	0.25410 (13)	0.75292 (16)	0.0535 (5)
N2	1.00732 (17)	0.16076 (10)	0.75046 (11)	0.0322 (3)
N3	1.01610 (18)	0.01092 (10)	0.85368 (11)	0.0331 (3)
N4	1.0037 (3)	−0.06823 (12)	0.89868 (16)	0.0478 (5)
H1N4	1.076 (3)	−0.0850 (16)	0.9461 (18)	0.057*
H2N4	0.909 (3)	−0.0860 (17)	0.892 (2)	0.057*
N5	0.8091 (3)	−0.09261 (13)	0.44379 (15)	0.0533 (5)
N6	0.82991 (18)	−0.00119 (10)	0.62587 (11)	0.0327 (3)
N7	0.65102 (18)	0.14165 (10)	0.63190 (12)	0.0330 (3)
N8	0.5788 (2)	0.22084 (12)	0.64252 (16)	0.0473 (4)
H1N8	0.493 (3)	0.2340 (17)	0.5969 (17)	0.057*
H2N8	0.568 (3)	0.2228 (17)	0.7042 (15)	0.057*
C1	1.1478 (3)	0.28105 (15)	0.69904 (19)	0.0508 (5)
H1	1.1414	0.3328	0.6607	0.061*
C2	1.0057 (2)	0.23502 (12)	0.69773 (16)	0.0405 (4)
H2	0.9065	0.2567	0.6589	0.049*
C3	1.1533 (2)	0.13197 (12)	0.80650 (14)	0.0329 (4)
C4	1.2941 (2)	0.18004 (14)	0.80619 (18)	0.0459 (5)
H4	1.3939	0.1593	0.8451	0.055*
C5	1.1551 (2)	0.05001 (13)	0.86525 (14)	0.0333 (4)
C6	1.3119 (2)	0.01689 (16)	0.93253 (16)	0.0478 (5)
H6A	1.2922	−0.0376	0.9643	0.072*
H6B	1.3546	0.0600	0.9847	0.072*
H6C	1.3894	0.0070	0.8919	0.072*
C7	0.9003 (3)	−0.12098 (14)	0.53299 (17)	0.0476 (5)
H7	0.9594	−0.1731	0.5344	0.057*
C8	0.9103 (3)	−0.07594 (12)	0.62350 (17)	0.0405 (4)
H8	0.9752	−0.0986	0.6843	0.049*
C9	0.7363 (2)	0.02954 (12)	0.53650 (14)	0.0321 (4)
C10	0.7270 (3)	−0.01761 (14)	0.44637 (15)	0.0433 (5)
H10	0.6608	0.0040	0.3854	0.052*
C11	0.6464 (2)	0.11247 (12)	0.54143 (14)	0.0332 (4)
C12	0.5611 (3)	0.15970 (16)	0.44551 (17)	0.0542 (6)
H12A	0.4486	0.1689	0.4459	0.081*
H12B	0.5671	0.1247	0.3868	0.081*
H12C	0.6128	0.2159	0.4422	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02815 (12)	0.03323 (12)	0.02997 (12)	−0.00097 (8)	0.00402 (8)	0.00062 (8)
Cl1	0.0421 (2)	0.0393 (3)	0.0413 (3)	0.00117 (19)	0.01106 (19)	−0.00545 (19)
Cl2	0.0444 (3)	0.0473 (3)	0.0443 (3)	−0.0159 (2)	0.0113 (2)	−0.0026 (2)
N1	0.0427 (10)	0.0487 (11)	0.0738 (14)	−0.0098 (8)	0.0232 (10)	−0.0013 (9)
N2	0.0295 (7)	0.0318 (7)	0.0353 (8)	−0.0001 (6)	0.0078 (6)	−0.0032 (6)
N3	0.0339 (8)	0.0326 (8)	0.0309 (8)	0.0006 (6)	0.0044 (6)	0.0015 (6)
N4	0.0466 (11)	0.0423 (10)	0.0485 (11)	−0.0012 (8)	−0.0003 (9)	0.0142 (8)
N5	0.0660 (13)	0.0522 (11)	0.0441 (11)	0.0055 (9)	0.0181 (9)	−0.0093 (8)
N6	0.0328 (8)	0.0319 (8)	0.0326 (8)	0.0006 (6)	0.0064 (6)	0.0008 (6)
N7	0.0286 (7)	0.0313 (7)	0.0390 (9)	0.0020 (6)	0.0081 (6)	0.0001 (6)
N8	0.0458 (10)	0.0413 (10)	0.0545 (11)	0.0136 (8)	0.0115 (9)	0.0010 (8)
C1	0.0531 (13)	0.0376 (11)	0.0671 (15)	−0.0016 (9)	0.0250 (11)	0.0061 (10)
C2	0.0400 (10)	0.0351 (10)	0.0466 (11)	0.0033 (8)	0.0110 (8)	0.0030 (8)
C3	0.0275 (8)	0.0381 (10)	0.0334 (9)	−0.0009 (7)	0.0084 (7)	−0.0060 (7)
C4	0.0317 (10)	0.0515 (12)	0.0557 (13)	−0.0047 (9)	0.0130 (9)	−0.0018 (10)
C5	0.0290 (9)	0.0412 (10)	0.0284 (9)	0.0034 (7)	0.0047 (7)	−0.0043 (7)
C6	0.0331 (10)	0.0616 (14)	0.0448 (12)	0.0089 (9)	0.0018 (9)	0.0065 (10)
C7	0.0530 (13)	0.0399 (11)	0.0527 (13)	0.0083 (9)	0.0185 (10)	−0.0033 (9)
C8	0.0412 (11)	0.0369 (10)	0.0432 (11)	0.0056 (8)	0.0098 (9)	0.0018 (8)
C9	0.0300 (8)	0.0349 (9)	0.0319 (9)	−0.0030 (7)	0.0083 (7)	0.0019 (7)
C10	0.0498 (12)	0.0462 (11)	0.0330 (10)	0.0011 (9)	0.0079 (9)	−0.0016 (8)
C11	0.0293 (9)	0.0340 (9)	0.0343 (9)	−0.0004 (7)	0.0042 (7)	0.0054 (7)
C12	0.0656 (15)	0.0501 (13)	0.0408 (12)	0.0119 (11)	0.0011 (10)	0.0117 (9)

Geometric parameters (Å, º) top

Zn1—N3	2.1568 (15)	N8—H2N8	0.857 (18)
Zn1—N7	2.1637 (15)	C1—C2	1.382 (3)
Zn1—N2	2.2408 (15)	C1—H1	0.9300
Zn1—N6	2.2600 (15)	C2—H2	0.9300
Zn1—Cl2	2.3620 (5)	C3—C4	1.392 (3)
Zn1—Cl1	2.3934 (5)	C3—C5	1.466 (3)
N1—C1	1.320 (3)	C4—H4	0.9300
N1—C4	1.326 (3)	C5—C6	1.493 (3)
N2—C2	1.325 (2)	C6—H6A	0.9600
N2—C3	1.349 (2)	C6—H6B	0.9600
N3—C5	1.288 (2)	C6—H6C	0.9600
N3—N4	1.355 (2)	C7—C8	1.377 (3)
N4—H1N4	0.806 (19)	C7—H7	0.9300
N4—H2N4	0.827 (19)	C8—H8	0.9300
N5—C7	1.326 (3)	C9—C10	1.389 (3)
N5—C10	1.333 (3)	C9—C11	1.474 (3)
N6—C8	1.322 (2)	C10—H10	0.9300
N6—C9	1.348 (2)	C11—C12	1.494 (3)
N7—C11	1.283 (2)	C12—H12A	0.9600
N7—N8	1.366 (2)	C12—H12B	0.9600
N8—H1N8	0.850 (19)	C12—H12C	0.9600

N3—Zn1—N7	154.76 (6)	N2—C2—H2	119.2
N3—Zn1—N2	73.96 (6)	C1—C2—H2	119.2
N7—Zn1—N2	87.67 (5)	N2—C3—C4	119.51 (18)
N3—Zn1—N6	88.53 (6)	N2—C3—C5	117.46 (16)
N7—Zn1—N6	73.43 (6)	C4—C3—C5	123.03 (17)
N2—Zn1—N6	88.17 (5)	N1—C4—C3	122.96 (19)
N3—Zn1—Cl2	95.08 (4)	N1—C4—H4	118.5
N7—Zn1—Cl2	101.28 (4)	C3—C4—H4	118.5
N2—Zn1—Cl2	168.11 (4)	N3—C5—C3	115.63 (15)
N6—Zn1—Cl2	86.94 (4)	N3—C5—C6	124.36 (18)
N3—Zn1—Cl1	99.25 (4)	C3—C5—C6	120.01 (17)
N7—Zn1—Cl1	97.78 (4)	C5—C6—H6A	109.5
N2—Zn1—Cl1	89.67 (4)	C5—C6—H6B	109.5
N6—Zn1—Cl1	171.02 (4)	H6A—C6—H6B	109.5
Cl2—Zn1—Cl1	96.76 (2)	C5—C6—H6C	109.5
C1—N1—C4	116.34 (18)	H6A—C6—H6C	109.5
C2—N2—C3	117.43 (16)	H6B—C6—H6C	109.5
C2—N2—Zn1	129.32 (13)	N5—C7—C8	122.3 (2)
C3—N2—Zn1	113.23 (12)	N5—C7—H7	118.9
C5—N3—N4	121.17 (16)	C8—C7—H7	118.9
C5—N3—Zn1	119.41 (12)	N6—C8—C7	121.45 (19)
N4—N3—Zn1	119.40 (13)	N6—C8—H8	119.3
N3—N4—H1N4	120.3 (19)	C7—C8—H8	119.3
N3—N4—H2N4	114.6 (18)	N6—C9—C10	119.67 (18)
H1N4—N4—H2N4	120 (3)	N6—C9—C11	116.67 (16)
C7—N5—C10	116.23 (18)	C10—C9—C11	123.65 (17)
C8—N6—C9	117.76 (17)	N5—C10—C9	122.61 (19)
C8—N6—Zn1	128.07 (13)	N5—C10—H10	118.7
C9—N6—Zn1	113.55 (12)	C9—C10—H10	118.7
C11—N7—N8	119.22 (16)	N7—C11—C9	115.91 (15)
C11—N7—Zn1	119.93 (12)	N7—C11—C12	123.24 (18)
N8—N7—Zn1	120.38 (13)	C9—C11—C12	120.81 (18)
N7—N8—H1N8	117.0 (17)	C11—C12—H12A	109.5
N7—N8—H2N8	106.8 (17)	C11—C12—H12B	109.5
H1N8—N8—H2N8	114 (2)	H12A—C12—H12B	109.5
N1—C1—C2	122.2 (2)	C11—C12—H12C	109.5
N1—C1—H1	118.9	H12A—C12—H12C	109.5
C2—C1—H1	118.9	H12B—C12—H12C	109.5
N2—C2—C1	121.55 (19)

N3—Zn1—N2—C2	178.63 (17)	C4—N1—C1—C2	0.0 (3)
N7—Zn1—N2—C2	16.15 (17)	C3—N2—C2—C1	0.6 (3)
N6—Zn1—N2—C2	89.63 (17)	Zn1—N2—C2—C1	178.73 (15)
Cl2—Zn1—N2—C2	155.39 (16)	N1—C1—C2—N2	−0.3 (3)
Cl1—Zn1—N2—C2	−81.65 (16)	C2—N2—C3—C4	−0.5 (3)
N3—Zn1—N2—C3	−3.15 (12)	Zn1—N2—C3—C4	−178.93 (14)
N7—Zn1—N2—C3	−165.63 (13)	C2—N2—C3—C5	179.72 (16)
N6—Zn1—N2—C3	−92.15 (13)	Zn1—N2—C3—C5	1.3 (2)
Cl2—Zn1—N2—C3	−26.4 (3)	C1—N1—C4—C3	0.1 (3)
Cl1—Zn1—N2—C3	96.57 (12)	N2—C3—C4—N1	0.1 (3)
N7—Zn1—N3—C5	50.1 (2)	C5—C3—C4—N1	179.9 (2)
N2—Zn1—N3—C5	5.20 (13)	N4—N3—C5—C3	175.73 (17)
N6—Zn1—N3—C5	93.72 (14)	Zn1—N3—C5—C3	−6.2 (2)
Cl2—Zn1—N3—C5	−179.49 (13)	N4—N3—C5—C6	−4.0 (3)
Cl1—Zn1—N3—C5	−81.77 (14)	Zn1—N3—C5—C6	174.13 (15)
N7—Zn1—N3—N4	−131.82 (16)	N2—C3—C5—N3	3.1 (3)
N2—Zn1—N3—N4	−176.68 (16)	C4—C3—C5—N3	−176.72 (18)
N6—Zn1—N3—N4	−88.16 (15)	N2—C3—C5—C6	−177.23 (17)
Cl2—Zn1—N3—N4	−1.36 (15)	C4—C3—C5—C6	3.0 (3)
Cl1—Zn1—N3—N4	96.35 (15)	C10—N5—C7—C8	0.0 (3)
N3—Zn1—N6—C8	23.01 (17)	C9—N6—C8—C7	0.4 (3)
N7—Zn1—N6—C8	−174.88 (17)	Zn1—N6—C8—C7	170.70 (15)
N2—Zn1—N6—C8	97.01 (17)	N5—C7—C8—N6	−0.5 (3)
Cl2—Zn1—N6—C8	−72.15 (16)	C8—N6—C9—C10	0.3 (3)
N3—Zn1—N6—C9	−166.32 (13)	Zn1—N6—C9—C10	−171.45 (14)
N7—Zn1—N6—C9	−4.21 (12)	C8—N6—C9—C11	179.32 (17)
N2—Zn1—N6—C9	−92.33 (13)	Zn1—N6—C9—C11	7.6 (2)
Cl2—Zn1—N6—C9	98.51 (12)	C7—N5—C10—C9	0.7 (3)
N3—Zn1—N7—C11	46.0 (2)	N6—C9—C10—N5	−0.8 (3)
N2—Zn1—N7—C11	88.76 (14)	C11—C9—C10—N5	−179.8 (2)
N6—Zn1—N7—C11	−0.03 (14)	N8—N7—C11—C9	176.15 (16)
Cl2—Zn1—N7—C11	−83.36 (14)	Zn1—N7—C11—C9	4.0 (2)
Cl1—Zn1—N7—C11	178.11 (14)	N8—N7—C11—C12	−1.8 (3)
N3—Zn1—N7—N8	−126.06 (16)	Zn1—N7—C11—C12	−174.00 (16)
N2—Zn1—N7—N8	−83.33 (14)	N6—C9—C11—N7	−7.9 (2)
N6—Zn1—N7—N8	−172.11 (15)	C10—C9—C11—N7	171.15 (18)
Cl2—Zn1—N7—N8	104.55 (14)	N6—C9—C11—C12	170.15 (18)
Cl1—Zn1—N7—N8	6.02 (14)	C10—C9—C11—C12	−10.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H2N8···Cl1	0.86 (2)	2.73 (2)	3.400 (2)	137 (2)
N8—H2N8···N1ⁱ	0.86 (2)	2.60 (2)	3.165 (3)	124 (2)
N4—H2N4···Cl2	0.83 (2)	2.60 (2)	3.250 (2)	137 (2)
N4—H1N4···Cl1ⁱⁱ	0.81 (2)	2.66 (2)	3.4429 (19)	165 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₆H₈N₄)₂]
M_r	408.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.4289 (8), 15.1128 (14), 13.4196 (13)
β (°)	104.077 (1)
V (Å³)	1658.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.81
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.713, 0.773
No. of measured, independent and observed [I > 2σ(I)] reflections	11576, 4132, 3456
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.03
No. of reflections	4132
No. of parameters	223
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.21

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H2N8···Cl1	0.857 (18)	2.73 (2)	3.400 (2)	137 (2)
N8—H2N8···N1ⁱ	0.857 (18)	2.60 (2)	3.165 (3)	124 (2)
N4—H2N4···Cl2	0.827 (19)	2.60 (2)	3.250 (2)	137 (2)
N4—H1N4···Cl1ⁱⁱ	0.806 (19)	2.66 (2)	3.4429 (19)	165 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+2.

Acknowledgements

We are thankful for the support of this study by the National Natural Science Foundation of China (No. 20871099 and J0730425) and Gansu provincial Natural Science Foundation of China (No. 0710RJZA113).

References

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