Dichloridobis(pyrazine-2-carboxamide-κN(4))zinc(II).

In the crystal of the title compound, [ZnCl(2)(C(5)H(5)N(3)O)(2)], the mol-ecule has m symmetry, with the Zn(II) cation and Cl(-) anions located on the mirror plane. The Zn(II) cation is coordinated by two Cl(-) anions and two pyrazine-2-carboxamide ligands in a distorted ZnCl(2)N(2) tetra-hedral geometry. The two pyrazine rings are nearly perpendicular to each other [dihedral angle = 86.61 (10)°]. Inter-molecular N-H⋯O and N-H⋯N hydrogen bonds and weak C-H⋯O inter-actions stabilize the crystal packing.

Related literature

For related structures, see: Abu-Youssef et al. (2006 ▶); Azhdari Tehrani et al. (2010 ▶); Goher & Mautner (2000 ▶); Kristiansson (2002 ▶); Mir Mohammad Sadegh et al. (2010 ▶); Munakata et al. (1997 ▶); Pacigova et al. (2008 ▶).

Experimental

Crystal data

[ZnCl2(C5n class="Species">H5N3O)2]

M = 382.53

Monoclinic,

a = 5.4296 (5) Å

b = 19.7629 (14) Å

c = 6.8396 (5) Å

β = 105.131 (7)°

V = 708.48 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.12 mm−1

T = 298 K

0.40 × 0.06 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector’ diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.881, T max = 0.902

5777 measured reflections

1441 independent reflections

1064 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.093

S = 0.97

1441 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013888/xu5500sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013888/xu5500Isup2.hkl

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

[ZnCl2(C5H5N3O)2]	F(000) = 384
Mr = 382.53	Dx = 1.793 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 5777 reflections
a = 5.4296 (5) Å	θ = 2.1–26.0°
b = 19.7629 (14) Å	µ = 2.12 mm−1
c = 6.8396 (5) Å	T = 298 K
β = 105.131 (7)°	Plate, colorless
V = 708.48 (10) Å3	0.40 × 0.06 × 0.05 mm
Z = 2

Bruker APEXII CCD area-detector' diffractometer	1441 independent reflections
Radiation source: fine-focus sealed tube	1064 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.881, Tmax = 0.902	k = −21→24
5777 measured reflections	l = −8→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
1441 reflections	(Δ/σ)max = 0.003
100 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.65 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	0.3963 (7)	0.3616 (2)	0.4810 (6)	0.0307 (9)
H1	0.2583	0.3512	0.3724	0.037*
C2	0.6226 (8)	0.3464 (2)	0.8085 (6)	0.0364 (10)
H2	0.6435	0.3262	0.9347	0.044*
C3	0.8016 (8)	0.3930 (2)	0.7802 (6)	0.0391 (10)
H3	0.9428	0.4022	0.8873	0.047*
C4	0.5722 (7)	0.4094 (2)	0.4563 (6)	0.0310 (8)
C5	0.5370 (8)	0.4445 (2)	0.2579 (6)	0.0366 (9)
N1	0.4213 (6)	0.33021 (16)	0.6574 (5)	0.0312 (7)
N2	0.7776 (6)	0.42473 (18)	0.6048 (5)	0.0366 (8)
N3	0.7336 (7)	0.4801 (2)	0.2331 (6)	0.0535 (11)
H3B	0.7210	0.5022	0.1226	0.064*
H3C	0.8736	0.4812	0.3276	0.064*
O1	0.3309 (6)	0.44069 (17)	0.1293 (4)	0.0506 (8)
Zn1	0.18582 (12)	0.2500	0.69002 (10)	0.0304 (2)
Cl1	0.1855 (3)	0.2500	1.0108 (2)	0.0480 (4)
Cl2	−0.1427 (3)	0.2500	0.4244 (2)	0.0416 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0264 (19)	0.030 (2)	0.034 (2)	−0.0008 (16)	0.0050 (17)	0.0030 (17)
C2	0.040 (2)	0.038 (2)	0.028 (2)	−0.0004 (18)	0.0041 (18)	0.0030 (18)
C3	0.036 (2)	0.046 (3)	0.030 (2)	−0.0092 (19)	−0.0004 (18)	0.0013 (19)
C4	0.0278 (19)	0.030 (2)	0.034 (2)	−0.0010 (16)	0.0063 (16)	−0.0002 (17)
C5	0.041 (2)	0.031 (2)	0.036 (2)	−0.0065 (18)	0.0050 (19)	0.0002 (18)
N1	0.0300 (16)	0.0295 (18)	0.0341 (19)	−0.0027 (14)	0.0081 (14)	−0.0011 (14)
N2	0.0325 (18)	0.037 (2)	0.037 (2)	−0.0053 (14)	0.0032 (15)	−0.0011 (15)
N3	0.041 (2)	0.073 (3)	0.042 (2)	−0.0229 (19)	0.0026 (17)	0.017 (2)
O1	0.0432 (17)	0.058 (2)	0.0413 (18)	−0.0198 (15)	−0.0053 (15)	0.0173 (16)
Zn1	0.0290 (3)	0.0313 (4)	0.0329 (4)	0.000	0.0114 (3)	0.000
Cl1	0.0570 (10)	0.0575 (11)	0.0328 (8)	0.000	0.0174 (7)	0.000
Cl2	0.0303 (7)	0.0525 (10)	0.0408 (8)	0.000	0.0069 (6)	0.000

C1—N1	1.332 (5)	C5—O1	1.232 (5)
C1—C4	1.384 (5)	C5—N3	1.326 (5)
C1—H1	0.9300	N1—Zn1	2.085 (3)
C2—N1	1.333 (5)	N3—H3B	0.8600
C2—C3	1.388 (6)	N3—H3C	0.8600
C2—H2	0.9300	Zn1—N1	2.085 (3)
C3—N2	1.330 (5)	Zn1—N1i	2.085 (3)
C3—H3	0.9300	Zn1—Cl1	2.1945 (16)
C4—N2	1.333 (5)	Zn1—Cl2	2.1888 (16)
C4—C5	1.491 (6)
N1—C1—C4	121.2 (4)	N3—C5—C4	116.6 (4)
N1—C1—H1	119.4	C1—N1—C2	117.4 (3)
C4—C1—H1	119.4	C1—N1—Zn1	122.1 (3)
N1—C2—C3	120.9 (4)	C2—N1—Zn1	120.1 (3)
N1—C2—H2	119.6	C3—N2—C4	116.4 (3)
C3—C2—H2	119.6	C5—N3—H3B	120.0
N2—C3—C2	122.1 (4)	C5—N3—H3C	120.0
N2—C3—H3	118.9	H3B—N3—H3C	120.0
C2—C3—H3	118.9	N1—Zn1—N1i	99.00 (18)
N2—C4—C1	121.9 (4)	N1—Zn1—Cl2	107.51 (10)
N2—C4—C5	118.1 (3)	N1i—Zn1—Cl2	107.51 (10)
C1—C4—C5	120.0 (3)	N1—Zn1—Cl1	105.53 (9)
O1—C5—N3	123.5 (4)	N1i—Zn1—Cl1	105.53 (9)
O1—C5—C4	119.9 (4)	Cl2—Zn1—Cl1	128.07 (6)
N1—C2—C3—N2	1.9 (7)	C3—C2—N1—Zn1	170.7 (3)
N1—C1—C4—N2	2.1 (6)	C2—C3—N2—C4	−0.2 (6)
N1—C1—C4—C5	−179.0 (4)	C1—C4—N2—C3	−1.7 (6)
N2—C4—C5—O1	−167.5 (4)	C5—C4—N2—C3	179.4 (4)
C1—C4—C5—O1	13.5 (6)	C1—N1—Zn1—N1i	96.5 (3)
N2—C4—C5—N3	10.8 (6)	C2—N1—Zn1—N1i	−75.5 (3)
C1—C4—C5—N3	−168.2 (4)	C1—N1—Zn1—Cl2	−15.2 (3)
C4—C1—N1—C2	−0.3 (6)	C2—N1—Zn1—Cl2	172.9 (3)
C4—C1—N1—Zn1	−172.5 (3)	C1—N1—Zn1—Cl1	−154.6 (3)
C3—C2—N1—C1	−1.5 (6)	C2—N1—Zn1—Cl1	33.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ii	0.86	2.02	2.875 (5)	175
N3—H3C···N2iii	0.86	2.61	3.205 (5)	128
C3—H3···O1iv	0.93	2.44	3.357 (5)	170

Table 1

Selected bond lengths (Å)

Zn1—N1	2.085 (3)
Zn1—Cl1	2.1945 (16)
Zn1—Cl2	2.1888 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1i	0.86	2.02	2.875 (5)	175
N3—H3C⋯N2ii	0.86	2.61	3.205 (5)	128
C3—H3⋯O1iii	0.93	2.44	3.357 (5)	170

Symmetry codes: (i) ; (ii) ; (iii) .