Tetra­kis(1-benzyl-1H-imidazole)dichlorido­nickel(II)

Li, H.; Sun, J.; Dai, X.

doi:10.1107/S1600536809014494

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m564

doi:10.1107/S1600536809014494

Open

access

Tetrakis(1-benzyl-1H-imidazole)dichloridonickel(II)

Hongjuan Li,^a ^* Jufeng Sun ^a and Xianping Dai ^a

^aSchool of Pharmacy, Binzhou Medical College, Yantai 264003, People's Republic of China
^*Correspondence e-mail: hjli80@163.com

(Received 10 April 2009; accepted 18 April 2009; online 25 April 2009)

In the title compound, [NiCl₂(C₁₀H₁₀N₂)₄], the Ni^II ion is located on an inversion center being coordinated by four N atoms from two pairs of symmetry-related 1-benzyl-1H-imidazole ligands and two chloride anions in a distorted octahedral geometry. Weak intermolecular C—H⋯Cl hydrogen bonds link the molecules into layers parallel to the ab plane.

Related literature

For general background to crystal engineering, see: Balamurugan et al. (2004 ); Desiraju (2007 ); Moulton & Zaworotko (2001 ). For applications of imidazole derivatives, see Lu et al. (2006 ); Huang et al. (2006 ). For details of the synthesis, see Owen et al. (2006 ).

Experimental

Crystal data

[NiCl₂(C₁₀H₁₀N₂)₄]
M_r = 762.41
Orthorhombic, P b c a
a = 7.296 (3) Å
b = 17.117 (4) Å
c = 29.651 (3) Å
V = 3703 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.71 mm⁻¹
T = 292 K
0.48 × 0.32 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: spherical (modified interpolation procedure; Dwiggins, 1975 ) T_min = 0.743, T_max = 0.745
4699 measured reflections
3207 independent reflections
1518 reflections with I > 2σ(I)
R_int = 0.011
3 standard reflections every 200 reflections intensity decay: 1.8%

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.231
S = 1.14
3207 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −1.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1ⁱ	0.93	2.77	3.617 (8)	151
C14—H14B⋯Cl1ⁱ	0.97	2.68	3.579 (8)	153
C13—H13⋯Cl1ⁱⁱ	0.93	2.71	3.561 (9)	152
Symmetry codes: (i) -x-1, -y, -z; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014494/cv2549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014494/cv2549Isup2.hkl

checkCIF report

Comment top

Crystal engineering, the rational design of functional molecular solids, is currently an active area of investigation because of its importance in supramolecular chemistry, materials science, and solid-state chemistry (Desiraju, 2007; Moulton & Zaworotko, 2001). It is noteworthy that a promising strategy for inorganic crystal engineering through combining non-covalent bonds such as van der Waals, π···π stacking and hydrogen bonds with coordination chemistry has attracted increasing attention in recent years (Balamurugan et al., 2004). Organic ligands are often used to coordinate to transition metals via coordinate bonds to generate metal complexes as the building blocks of the assembly. Imidazole and its derivatives are ubiquitous in biological and biochemical structure and function and thus attracted special attention in the construction of some interesting metal-organic frameworks in recent years (Huang et al., 2006; Lu et al., 2006). Here, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), each Ni^II ion displays a slightly distorted octahedral coordination geometry defined by four 1-benzyl-1H-imidazole ligands and two chloride anions. The Ni—N bond lengths are in the range of 2.070 (5) Å to 2.140 (3) Å and the Ni—Cl bond lengths is 2.468 (2) Å. Weak intermolecular C—H···Cl hydrogen bonds (Table 1) enhance the crystal packing stability.

Related literature top

For general background to crystal engineering, see: Balamurugan et al. (2004); Desiraju (2007); Moulton & Zaworotko (2001). For applications of imidazole derivatives, see Lu et al. (2006); Huang et al. (2006). For details of the synthesis, see Owen et al. (2006).

Experimental top

The 1-benzyl-1H-imidazole was prepared according to the literature (Owen et al., 2006). Nickel (II) chloride hexahydrate (1 mmol, 0.24 g) and 1-benzyl-1H-imidazole (4 mmol, 0.63 g) were mixed in chloroform (15 ml) and the mixture was stirred for 5 h at room temperature. After filtration, the solid was dissolved in methanol (8 ml). Green crystals suitable for X-ray analysis were obtained by slow evaporation of this solution over a period of six days.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering. The unlabelled atoms are related with the labelled ones by symmetry element (-x, -y, -z).

Tetrakis(1-benzyl-1H-imidazole)dichloridonickel(II) top

Crystal data top

[NiCl₂(C₁₀H₁₀N₂)₄]	F(000) = 1592
M_r = 762.41	D_x = 1.368 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 20 reflections
a = 7.296 (3) Å	θ = 5.7–6.9°
b = 17.117 (4) Å	µ = 0.71 mm⁻¹
c = 29.651 (3) Å	T = 292 K
V = 3703 (2) Å³	Block, green
Z = 4	0.48 × 0.32 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.011
Graphite monochromator	θ_max = 25.6°, θ_min = 2.8°
ω/2θ scans	h = −1→8
Absorption correction: for a sphere (modified interpolation procedure; Dwiggins, 1975)	k = −2→20
T_min = 0.743, T_max = 0.745	l = −9→35
4699 measured reflections	3 standard reflections every 200 reflections
3207 independent reflections	intensity decay: 1.9%

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) = 0.231	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0948P)²] where P = (F_o² + 2F_c²)/3
3207 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.72 e Å⁻³
1 restraint	Δρ_min = −1.42 e Å⁻³

Crystal data top

[NiCl₂(C₁₀H₁₀N₂)₄]	V = 3703 (2) Å³
M_r = 762.41	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 7.296 (3) Å	µ = 0.71 mm⁻¹
b = 17.117 (4) Å	T = 292 K
c = 29.651 (3) Å	0.48 × 0.32 × 0.30 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1518 reflections with I > 2σ(I)
Absorption correction: for a sphere (modified interpolation procedure; Dwiggins, 1975)	R_int = 0.011
T_min = 0.743, T_max = 0.745	3 standard reflections every 200 reflections
4699 measured reflections	intensity decay: 1.9%
3207 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	1 restraint
wR(F²) = 0.231	H-atom parameters constrained
S = 1.14	Δρ_max = 0.72 e Å⁻³
3207 reflections	Δρ_min = −1.42 e Å⁻³
220 parameters

Special details top

Experimental. In spherical absoprtion correction, interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0–2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6–10.0, was used. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146–148) was used with some modification.

The most probable reason for a large number of missing reflections - 238 - lies in the fact that it is very difficult to obtain high quality crystal. After we collected the reflections of the crystal, we couldn't gain perfect crystal data. To get better and reasonable structure of the crystal, those reflections which seriously influence the optimization of the crystal structure were omitted during the course of refinement of the data.

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
Ni1	0.0000	0.0000	0.0000	0.0340 (4)
Cl1	−0.2771 (3)	−0.07775 (10)	−0.01632 (6)	0.0466 (5)
N1	−0.1100 (8)	0.0385 (3)	0.06038 (16)	0.0359 (13)
N2	−0.2920 (9)	0.0980 (3)	0.10849 (18)	0.0471 (16)
N3	−0.1313 (8)	0.0963 (3)	−0.03282 (17)	0.0408 (14)
N4	−0.3505 (9)	0.1751 (3)	−0.05553 (17)	0.0458 (16)
C1	−0.2707 (11)	0.0710 (4)	0.0662 (2)	0.0459 (18)
H1	−0.3595	0.0749	0.0438	0.055*
C2	−0.0234 (12)	0.0452 (5)	0.1010 (2)	0.053 (2)
H2	0.0941	0.0271	0.1073	0.063*
C3	−0.1335 (12)	0.0818 (5)	0.1306 (2)	0.057 (2)
H3	−0.1062	0.0938	0.1604	0.068*
C4	−0.4477 (13)	0.1410 (5)	0.1252 (2)	0.062 (3)
H4A	−0.5317	0.1503	0.1004	0.075*
H4B	−0.4061	0.1914	0.1360	0.075*
C5	−0.5503 (11)	0.1003 (5)	0.1627 (2)	0.048 (2)
C6	−0.6202 (12)	0.1452 (5)	0.1977 (2)	0.058 (2)
H6	−0.5998	0.1988	0.1988	0.069*
C7	−0.7196 (15)	0.1086 (8)	0.2304 (3)	0.090 (4)
H7	−0.7623	0.1384	0.2545	0.107*
C8	−0.7590 (18)	0.0333 (9)	0.2301 (3)	0.102 (4)
H8	−0.8334	0.0117	0.2523	0.123*
C9	−0.6870 (18)	−0.0131 (6)	0.1959 (4)	0.088 (3)
H9	−0.7085	−0.0666	0.1956	0.106*
C10	−0.5826 (14)	0.0214 (5)	0.1620 (3)	0.068 (3)
H10	−0.5346	−0.0091	0.1389	0.081*
C11	−0.3010 (12)	0.1020 (4)	−0.0462 (2)	0.0489 (19)
H11	−0.3794	0.0594	−0.0489	0.059*
C12	−0.0682 (11)	0.1720 (4)	−0.0329 (2)	0.0479 (19)
H12	0.0495	0.1871	−0.0246	0.057*
C13	−0.2007 (13)	0.2212 (5)	−0.0467 (2)	0.057 (2)
H13	−0.1926	0.2752	−0.0496	0.068*
C14	−0.5292 (11)	0.2037 (5)	−0.0674 (2)	0.059 (2)
H14A	−0.5335	0.2594	−0.0614	0.071*
H14B	−0.6191	0.1789	−0.0480	0.071*
C15	−0.5830 (8)	0.1897 (3)	−0.11593 (13)	0.051 (2)
C16	−0.4895 (7)	0.2276 (3)	−0.15044 (17)	0.069 (2)
H16	−0.3905	0.2597	−0.1437	0.083*
C17	−0.5439 (10)	0.2173 (4)	−0.19497 (14)	0.091 (4)
H17	−0.4814	0.2426	−0.2181	0.109*
C18	−0.6919 (10)	0.1692 (4)	−0.20499 (17)	0.106 (4)
H18	−0.7283	0.1623	−0.2348	0.127*
C19	−0.7854 (8)	0.1313 (4)	−0.1705 (3)	0.102 (4)
H19	−0.8844	0.0991	−0.1772	0.122*
C20	−0.7310 (8)	0.1416 (3)	−0.1260 (2)	0.071 (3)
H20	−0.7935	0.1163	−0.1029	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0249 (7)	0.0408 (7)	0.0363 (6)	0.0012 (6)	0.0032 (6)	−0.0016 (5)
Cl1	0.0319 (11)	0.0484 (11)	0.0597 (9)	−0.0045 (8)	−0.0011 (8)	−0.0002 (8)
N1	0.019 (3)	0.050 (3)	0.039 (3)	0.001 (3)	0.006 (3)	−0.002 (2)
N2	0.044 (4)	0.051 (4)	0.046 (3)	0.013 (3)	0.008 (3)	−0.004 (3)
N3	0.013 (3)	0.069 (4)	0.040 (3)	0.007 (3)	0.000 (3)	0.006 (3)
N4	0.042 (4)	0.053 (4)	0.042 (3)	0.026 (3)	0.006 (3)	0.005 (3)
C1	0.037 (5)	0.068 (5)	0.033 (3)	0.007 (4)	0.007 (3)	0.005 (3)
C2	0.037 (5)	0.072 (5)	0.049 (4)	0.014 (4)	−0.001 (4)	−0.008 (4)
C3	0.043 (5)	0.081 (6)	0.047 (4)	−0.001 (4)	−0.002 (4)	−0.011 (4)
C4	0.059 (7)	0.068 (6)	0.060 (5)	0.028 (4)	0.024 (4)	0.009 (4)
C5	0.033 (5)	0.071 (6)	0.040 (4)	0.014 (4)	0.001 (3)	−0.005 (3)
C6	0.045 (6)	0.084 (6)	0.045 (4)	0.019 (5)	−0.004 (4)	−0.004 (4)
C7	0.057 (7)	0.161 (11)	0.051 (5)	0.022 (7)	0.019 (5)	0.012 (6)
C8	0.076 (10)	0.147 (11)	0.084 (7)	0.005 (8)	0.033 (7)	0.047 (8)
C9	0.083 (9)	0.077 (7)	0.104 (7)	−0.011 (6)	−0.009 (7)	0.026 (6)
C10	0.064 (7)	0.080 (6)	0.060 (5)	0.005 (5)	0.003 (5)	0.000 (4)
C11	0.050 (5)	0.059 (5)	0.037 (3)	0.012 (4)	−0.007 (4)	0.003 (3)
C12	0.031 (5)	0.059 (5)	0.054 (4)	−0.009 (4)	0.014 (4)	0.005 (4)
C13	0.057 (6)	0.056 (5)	0.057 (4)	−0.006 (4)	−0.001 (4)	0.003 (4)
C14	0.041 (6)	0.085 (6)	0.052 (4)	0.029 (4)	0.017 (4)	0.011 (4)
C15	0.042 (5)	0.052 (5)	0.058 (4)	0.013 (4)	−0.002 (4)	0.010 (3)
C16	0.072 (7)	0.078 (6)	0.057 (5)	−0.003 (5)	0.004 (5)	0.014 (4)
C17	0.100 (10)	0.128 (9)	0.046 (5)	0.016 (7)	−0.010 (6)	0.014 (5)
C18	0.119 (13)	0.114 (10)	0.086 (7)	0.041 (8)	−0.031 (8)	−0.027 (6)
C19	0.073 (9)	0.105 (9)	0.127 (9)	−0.011 (6)	−0.012 (8)	−0.035 (7)
C20	0.056 (7)	0.059 (6)	0.100 (7)	−0.003 (5)	0.009 (6)	0.001 (5)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.070 (5)	C6—H6	0.9300
Ni1—N1	2.070 (5)	C7—C8	1.320 (15)
Ni1—N3	2.140 (6)	C7—H7	0.9300
Ni1—N3ⁱ	2.140 (6)	C8—C9	1.391 (15)
Ni1—Cl1	2.468 (2)	C8—H8	0.9300
Ni1—Cl1ⁱ	2.468 (2)	C9—C10	1.392 (13)
N1—C1	1.310 (9)	C9—H9	0.9300
N1—C2	1.365 (8)	C10—H10	0.9300
N2—C1	1.345 (8)	C11—H11	0.9300
N2—C3	1.358 (10)	C12—C13	1.345 (11)
N2—C4	1.441 (9)	C12—H12	0.9300
N3—C11	1.304 (9)	C13—H13	0.9300
N3—C12	1.376 (8)	C14—C15	1.512 (8)
N4—C11	1.333 (8)	C14—H14A	0.9700
N4—C13	1.373 (10)	C14—H14B	0.9700
N4—C14	1.436 (9)	C15—C16	1.3900
C1—H1	0.9300	C15—C20	1.3900
C2—C3	1.345 (10)	C16—C17	1.3900
C2—H2	0.9300	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.3900
C4—C5	1.510 (10)	C17—H17	0.9300
C4—H4A	0.9700	C18—C19	1.3900
C4—H4B	0.9700	C18—H18	0.9300
C5—C10	1.371 (10)	C19—C20	1.3900
C5—C6	1.389 (9)	C19—H19	0.9300
C6—C7	1.365 (13)	C20—H20	0.9300

N1ⁱ—Ni1—N1	180.0	C5—C6—H6	120.9
N1ⁱ—Ni1—N3	91.4 (2)	C8—C7—C6	124.0 (10)
N1—Ni1—N3	88.6 (2)	C8—C7—H7	118.0
N1ⁱ—Ni1—N3ⁱ	88.6 (2)	C6—C7—H7	118.0
N1—Ni1—N3ⁱ	91.4 (2)	C7—C8—C9	118.7 (10)
N3—Ni1—N3ⁱ	180.0	C7—C8—H8	120.6
N1ⁱ—Ni1—Cl1	88.65 (16)	C9—C8—H8	120.6
N1—Ni1—Cl1	91.35 (16)	C8—C9—C10	119.4 (10)
N3—Ni1—Cl1	87.67 (17)	C8—C9—H9	120.3
N3ⁱ—Ni1—Cl1	92.33 (17)	C10—C9—H9	120.3
N1ⁱ—Ni1—Cl1ⁱ	91.35 (16)	C5—C10—C9	120.0 (9)
N1—Ni1—Cl1ⁱ	88.65 (16)	C5—C10—H10	120.0
N3—Ni1—Cl1ⁱ	92.33 (17)	C9—C10—H10	120.0
N3ⁱ—Ni1—Cl1ⁱ	87.67 (17)	N3—C11—N4	113.0 (7)
Cl1—Ni1—Cl1ⁱ	180.0	N3—C11—H11	123.5
C1—N1—C2	105.2 (6)	N4—C11—H11	123.5
C1—N1—Ni1	126.6 (5)	C13—C12—N3	110.4 (8)
C2—N1—Ni1	127.6 (5)	C13—C12—H12	124.8
C1—N2—C3	106.3 (6)	N3—C12—H12	124.8
C1—N2—C4	125.9 (7)	C12—C13—N4	105.7 (7)
C3—N2—C4	127.6 (6)	C12—C13—H13	127.1
C11—N3—C12	104.3 (6)	N4—C13—H13	127.1
C11—N3—Ni1	128.4 (5)	N4—C14—C15	114.5 (6)
C12—N3—Ni1	125.2 (5)	N4—C14—H14A	108.6
C11—N4—C13	106.5 (7)	C15—C14—H14A	108.6
C11—N4—C14	128.1 (7)	N4—C14—H14B	108.6
C13—N4—C14	125.0 (7)	C15—C14—H14B	108.6
N1—C1—N2	111.9 (6)	H14A—C14—H14B	107.6
N1—C1—H1	124.1	C16—C15—C20	120.0
N2—C1—H1	124.1	C16—C15—C14	120.0 (5)
C3—C2—N1	109.8 (7)	C20—C15—C14	119.9 (5)
C3—C2—H2	125.1	C17—C16—C15	120.0
N1—C2—H2	125.1	C17—C16—H16	120.0
C2—C3—N2	106.8 (6)	C15—C16—H16	120.0
C2—C3—H3	126.6	C18—C17—C16	120.0
N2—C3—H3	126.6	C18—C17—H17	120.0
N2—C4—C5	114.1 (6)	C16—C17—H17	120.0
N2—C4—H4A	108.7	C17—C18—C19	120.0
C5—C4—H4A	108.7	C17—C18—H18	120.0
N2—C4—H4B	108.7	C19—C18—H18	120.0
C5—C4—H4B	108.7	C20—C19—C18	120.0
H4A—C4—H4B	107.6	C20—C19—H19	120.0
C10—C5—C6	119.6 (8)	C18—C19—H19	120.0
C10—C5—C4	121.8 (7)	C19—C20—C15	120.0
C6—C5—C4	118.5 (8)	C19—C20—H20	120.0
C7—C6—C5	118.2 (9)	C15—C20—H20	120.0
C7—C6—H6	120.9

N1ⁱ—Ni1—N1—C1	−158 (20)	N2—C4—C5—C10	−40.6 (12)
N3—Ni1—N1—C1	35.5 (6)	N2—C4—C5—C6	142.2 (8)
N3ⁱ—Ni1—N1—C1	−144.5 (6)	C10—C5—C6—C7	−0.1 (12)
Cl1—Ni1—N1—C1	−52.1 (6)	C4—C5—C6—C7	177.2 (8)
Cl1ⁱ—Ni1—N1—C1	127.9 (6)	C5—C6—C7—C8	−2.4 (15)
N1ⁱ—Ni1—N1—C2	32 (22)	C6—C7—C8—C9	3.8 (18)
N3—Ni1—N1—C2	−135.0 (6)	C7—C8—C9—C10	−2.7 (18)
N3ⁱ—Ni1—N1—C2	45.0 (6)	C6—C5—C10—C9	0.9 (13)
Cl1—Ni1—N1—C2	137.4 (6)	C4—C5—C10—C9	−176.2 (9)
Cl1ⁱ—Ni1—N1—C2	−42.6 (6)	C8—C9—C10—C5	0.4 (16)
N1ⁱ—Ni1—N3—C11	98.3 (6)	C12—N3—C11—N4	1.1 (7)
N1—Ni1—N3—C11	−81.7 (6)	Ni1—N3—C11—N4	165.0 (4)
N3ⁱ—Ni1—N3—C11	−77 (56)	C13—N4—C11—N3	−1.2 (8)
Cl1—Ni1—N3—C11	9.8 (6)	C14—N4—C11—N3	−174.3 (6)
Cl1ⁱ—Ni1—N3—C11	−170.2 (6)	C11—N3—C12—C13	−0.6 (8)
N1ⁱ—Ni1—N3—C12	−100.9 (5)	Ni1—N3—C12—C13	−165.1 (5)
N1—Ni1—N3—C12	79.1 (5)	N3—C12—C13—N4	−0.1 (8)
N3ⁱ—Ni1—N3—C12	84 (56)	C11—N4—C13—C12	0.8 (8)
Cl1—Ni1—N3—C12	170.5 (5)	C14—N4—C13—C12	174.2 (6)
Cl1ⁱ—Ni1—N3—C12	−9.5 (5)	C11—N4—C14—C15	−79.1 (9)
C2—N1—C1—N2	−0.2 (8)	C13—N4—C14—C15	109.0 (8)
Ni1—N1—C1—N2	−172.4 (4)	N4—C14—C15—C16	−66.5 (8)
C3—N2—C1—N1	0.4 (8)	N4—C14—C15—C20	116.2 (7)
C4—N2—C1—N1	176.0 (7)	C20—C15—C16—C17	0.0
C1—N1—C2—C3	−0.2 (9)	C14—C15—C16—C17	−177.2 (5)
Ni1—N1—C2—C3	171.9 (5)	C15—C16—C17—C18	0.0
N1—C2—C3—N2	0.4 (10)	C16—C17—C18—C19	0.0
C1—N2—C3—C2	−0.5 (9)	C17—C18—C19—C20	0.0
C4—N2—C3—C2	−176.0 (7)	C18—C19—C20—C15	0.0
C1—N2—C4—C5	117.9 (8)	C16—C15—C20—C19	0.0
C3—N2—C4—C5	−67.5 (12)	C14—C15—C20—C19	177.2 (5)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱⁱ	0.93	2.77	3.617 (8)	151
C14—H14B···Cl1ⁱⁱ	0.97	2.68	3.579 (8)	153
C13—H13···Cl1ⁱⁱⁱ	0.93	2.71	3.561 (9)	152

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

Experimental details

Crystal data
Chemical formula	[NiCl₂(C₁₀H₁₀N₂)₄]
M_r	762.41
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	7.296 (3), 17.117 (4), 29.651 (3)
V (Å³)	3703 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.48 × 0.32 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	For a sphere (modified interpolation procedure; Dwiggins, 1975)
T_min, T_max	0.743, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	4699, 3207, 1518
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.231, 1.14
No. of reflections	3207
No. of parameters	220
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −1.42

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1ⁱ	0.93	2.77	3.617 (8)	151
C14—H14B···Cl1ⁱ	0.97	2.68	3.579 (8)	153
C13—H13···Cl1ⁱⁱ	0.93	2.71	3.561 (9)	152

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

Acknowledgements

The authors are grateful to Binzhou Medical College for financial support (grant No. BY2007KJ13).

References

Balamurugan, V., Hundal, M. S. & Mukherjee, R. (2004). Chem. Eur. J. 10, 1683–1690. Web of Science CSD CrossRef PubMed CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 45, 8342–8356. Web of Science CrossRef Google Scholar
Dwiggins, C. W. (1975). Acta Cryst. A31, 146–148. CrossRef IUCr Journals Web of Science Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting, Abstract PA104. Google Scholar
Huang, X. C., Lin, Y. Y., Zhang, J. P. & Chen, X. M. (2006). Angew. Chem. Int. Ed. 45, 1557–1559. Web of Science CSD CrossRef CAS Google Scholar
Lu, W. G., Su, C. Y., Lu, T. B., Jiang, L. & Chen, J. M. (2006). J. Am. Chem. Soc. 128, 34–35. Web of Science CSD CrossRef PubMed CAS Google Scholar
Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629–1658. Web of Science CrossRef PubMed CAS Google Scholar
Owen, C. P., Dhanani, S., Patel, C. H., Shahid, I. & Ahmed, S. (2006). Bioorg. Med. Chem. Lett. pp. 4011–4015. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar