trans-Diamminedichloridobis(1H-imidazole-κN (3))nickel(II).

The whole mol-ecule of the title compound, [NiCl2(C3H4N2)2(NH3)2], is generated by inversion symmetry. The Ni(II) ion, which is located on an inversion center, has a distorted octa-hedral coordination environment and is surrounded by two ammine N atoms and two Cl atoms in the equatorial plane, with two N atoms of two imidazole groups occupying the axial positions. The imidazole ring makes a dihedral angle of 81.78 (18)° with the Ni/N/Cl equatorial plane. In the crystal, mol-ecules are linked via N-H⋯Cl hydrogen bonds and C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For applications of imidazole and its derivatives, see: Huang et al. (2008 ▶, 2011 ▶). For the biological activity of imidazole deriv­atives, see: Gaonkar et al. (2009 ▶).

Experimental

Crystal data

[NiCl2(C3H4N2)2(NH3)2]

M = 299.82

Orthorhombic,

a = 9.1349 (9) Å

b = 7.9451 (5) Å

c = 15.6121 (13) Å

V = 1133.09 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.16 mm−1

T = 293 K

0.5 × 0.4 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.369, T max = 0.421

4464 measured reflections

1338 independent reflections

1137 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.11

1338 reflections

71 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −1.00 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016747/su2612sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016747/su2612Isup2.hkl

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

[NiCl2(C3H4N2)2(NH3)2]	F(000) = 616
Mr = 299.82	Dx = 1.758 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1338 reflections
a = 9.1349 (9) Å	θ = 5.2–29.1°
b = 7.9451 (5) Å	µ = 2.16 mm−1
c = 15.6121 (13) Å	T = 293 K
V = 1133.09 (16) Å3	Block, green
Z = 4	0.5 × 0.4 × 0.4 mm

Oxford Diffraction Xcalibur Eos diffractometer	1338 independent reflections
Radiation source: fine-focus sealed tube	1137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 15.9821 pixels mm-1	θmax = 29.1°, θmin = 5.2°
ω and φ scan	h = −8→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.369, Tmax = 0.421	l = −21→15
4464 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0565P)2 + 3.9561P] where P = (Fo2 + 2Fc2)/3
1338 reflections	(Δ/σ)max < 0.001
71 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −1.00 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C4	0.1725 (5)	0.0044 (5)	0.3343 (3)	0.0331 (9)
H4	0.2329	−0.0824	0.3530	0.040*
C6	0.0749 (5)	0.1968 (6)	0.2518 (3)	0.0369 (9)
H6	0.0539	0.2659	0.2053	0.044*
C7	0.0103 (4)	0.1991 (5)	0.3298 (2)	0.0288 (8)
H7	−0.0643	0.2720	0.3462	0.035*
Cl2	−0.25211 (9)	−0.00290 (10)	0.44598 (5)	0.0227 (2)
N3	0.0715 (3)	0.0774 (4)	0.38102 (17)	0.0209 (6)
N5	0.1766 (4)	0.0725 (5)	0.2555 (2)	0.0372 (8)
H5	0.2338	0.0425	0.2145	0.045*
N8	−0.0253 (3)	0.2503 (3)	0.53954 (16)	0.0128 (5)
H8A	−0.0989	0.2973	0.5109	0.015*
H8B	0.0568	0.3070	0.5292	0.015*
H8C	−0.0446	0.2530	0.5954	0.015*
Ni1	0.0000	0.0000	0.5000	0.0150 (2)

	U11	U22	U33	U12	U13	U23
C4	0.031 (2)	0.041 (2)	0.0275 (19)	0.0049 (16)	0.0083 (16)	0.0018 (15)
C6	0.040 (2)	0.050 (2)	0.0203 (16)	−0.0078 (19)	0.0006 (16)	0.0116 (18)
C7	0.0277 (19)	0.035 (2)	0.0233 (17)	0.0025 (15)	0.0011 (14)	0.0094 (15)
Cl2	0.0183 (4)	0.0255 (4)	0.0242 (4)	−0.0017 (3)	−0.0041 (3)	0.0038 (3)
N3	0.0209 (14)	0.0267 (14)	0.0152 (12)	−0.0010 (11)	0.0022 (11)	0.0021 (11)
N5	0.0391 (19)	0.052 (2)	0.0206 (14)	−0.0066 (17)	0.0140 (14)	−0.0034 (15)
N8	0.0144 (11)	0.0118 (10)	0.0123 (10)	0.0009 (9)	−0.0010 (9)	−0.0004 (9)
Ni1	0.0151 (3)	0.0177 (3)	0.0123 (3)	0.00026 (19)	−0.00016 (19)	0.00066 (19)

C4—N3	1.312 (5)	N3—Ni1	2.063 (3)
C4—N5	1.345 (5)	N5—H5	0.8600
C4—H4	0.9300	N8—Ni1	2.095 (2)
C6—C7	1.353 (6)	N8—H8A	0.8900
C6—N5	1.357 (6)	N8—H8B	0.8900
C6—H6	0.9300	N8—H8C	0.8900
C7—N3	1.374 (5)	Ni1—N3i	2.063 (3)
C7—H7	0.9300	Ni1—N8i	2.095 (2)
Cl2—Ni1	2.4527 (9)	Ni1—Cl2i	2.4527 (9)
N3—C4—N5	110.5 (4)	Ni1—N8—H8C	109.5
N3—C4—H4	124.7	H8A—N8—H8C	109.5
N5—C4—H4	124.7	H8B—N8—H8C	109.5
C7—C6—N5	105.7 (3)	N3i—Ni1—N3	180.0
C7—C6—H6	127.1	N3i—Ni1—N8	89.00 (11)
N5—C6—H6	127.1	N3—Ni1—N8	91.00 (11)
C6—C7—N3	109.7 (4)	N3i—Ni1—N8i	91.00 (11)
C6—C7—H7	125.2	N3—Ni1—N8i	89.00 (11)
N3—C7—H7	125.2	N8—Ni1—N8i	180.0
C4—N3—C7	105.9 (3)	N3i—Ni1—Cl2i	89.45 (8)
C4—N3—Ni1	126.3 (3)	N3—Ni1—Cl2i	90.55 (8)
C7—N3—Ni1	127.2 (2)	N8—Ni1—Cl2i	89.62 (7)
C4—N5—C6	108.2 (3)	N8i—Ni1—Cl2i	90.38 (7)
C4—N5—H5	125.9	N3i—Ni1—Cl2	90.55 (8)
C6—N5—H5	125.9	N3—Ni1—Cl2	89.45 (8)
Ni1—N8—H8A	109.5	N8—Ni1—Cl2	90.38 (7)
Ni1—N8—H8B	109.5	N8i—Ni1—Cl2	89.62 (7)
H8A—N8—H8B	109.5	Cl2i—Ni1—Cl2	180.0
N5—C6—C7—N3	−0.1 (5)	C4—N3—Ni1—N8	143.9 (3)
N5—C4—N3—C7	−0.9 (5)	C7—N3—Ni1—N8	−46.1 (3)
N5—C4—N3—Ni1	170.8 (3)	C4—N3—Ni1—N8i	−36.1 (3)
C6—C7—N3—C4	0.6 (5)	C7—N3—Ni1—N8i	133.9 (3)
C6—C7—N3—Ni1	−171.1 (3)	C4—N3—Ni1—Cl2i	54.3 (3)
N3—C4—N5—C6	0.9 (5)	C7—N3—Ni1—Cl2i	−135.7 (3)
C7—C6—N5—C4	−0.5 (5)	C4—N3—Ni1—Cl2	−125.7 (3)
C4—N3—Ni1—N3i	126 (8)	C7—N3—Ni1—Cl2	44.3 (3)
C7—N3—Ni1—N3i	−64 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···Cl2ii	0.86	2.53	3.268 (3)	144
N8—H8A···Cl2iii	0.89	2.32	3.180 (3)	162
N8—H8B···Cl2iv	0.89	2.37	3.210 (3)	157
C4—H4···Cg1v	0.93	2.95	3.772 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3/C4/N5/C6/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯Cl2i	0.86	2.53	3.268 (3)	144
N8—H8A⋯Cl2ii	0.89	2.32	3.180 (3)	162
N8—H8B⋯Cl2iii	0.89	2.37	3.210 (3)	157
C4—H4⋯Cg1iv	0.93	2.95	3.772 (5)	148

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