Literature DB >> 21583795

Tetra-kis(1-benzyl-1H-imidazole)dichlorido-nickel(II).

Hongjuan Li1, Jufeng Sun, Xianping Dai.   

Abstract

In the title compound, [NiCl(2)(C(10)H(10)N(2))(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 octa-hedral geometry. Weak inter-molecular C-H⋯Cl hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

Entities:  

Year:  2009        PMID： 21583795      PMCID： PMC2977609          DOI： 10.1107/S1600536809014494

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 762.41 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.079 wR(F 2) = 0.231 S = 1.14 3207 reflections 220 parameters 1 restraint H-atom parameters constrained Δρmax = 0.72 e Å−3 Δρmin = −1.42 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014494/cv2549sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014494/cv2549Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[NiCl2(C10H10N2)4]F(000) = 1592
Mr = 762.41Dx = 1.368 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 20 reflections
a = 7.296 (3) Åθ = 5.7–6.9°
b = 17.117 (4) ŵ = 0.71 mm−1
c = 29.651 (3) ÅT = 292 K
V = 3703 (2) Å3Block, green
Z = 40.48 × 0.32 × 0.30 mm
Enraf–Nonius CAD-4 diffractometer1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
graphiteθmax = 25.6°, θmin = 2.8°
ω/2θ scansh = −1→8
Absorption correction: for a sphere (modified interpolation procedure; Dwiggins, 1975)k = −2→20
Tmin = 0.743, Tmax = 0.745l = −9→35
4699 measured reflections3 standard reflections every 200 reflections
3207 independent reflections intensity decay: 1.9%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0948P)2] where P = (Fo2 + 2Fc2)/3
3207 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.72 e Å−3
1 restraintΔρmin = −1.42 e Å−3
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.
xyzUiso*/Ueq
Ni10.00000.00000.00000.0340 (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)
H1−0.35950.07490.04380.055*
C2−0.0234 (12)0.0452 (5)0.1010 (2)0.053 (2)
H20.09410.02710.10730.063*
C3−0.1335 (12)0.0818 (5)0.1306 (2)0.057 (2)
H3−0.10620.09380.16040.068*
C4−0.4477 (13)0.1410 (5)0.1252 (2)0.062 (3)
H4A−0.53170.15030.10040.075*
H4B−0.40610.19140.13600.075*
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)
H6−0.59980.19880.19880.069*
C7−0.7196 (15)0.1086 (8)0.2304 (3)0.090 (4)
H7−0.76230.13840.25450.107*
C8−0.7590 (18)0.0333 (9)0.2301 (3)0.102 (4)
H8−0.83340.01170.25230.123*
C9−0.6870 (18)−0.0131 (6)0.1959 (4)0.088 (3)
H9−0.7085−0.06660.19560.106*
C10−0.5826 (14)0.0214 (5)0.1620 (3)0.068 (3)
H10−0.5346−0.00910.13890.081*
C11−0.3010 (12)0.1020 (4)−0.0462 (2)0.0489 (19)
H11−0.37940.0594−0.04890.059*
C12−0.0682 (11)0.1720 (4)−0.0329 (2)0.0479 (19)
H120.04950.1871−0.02460.057*
C13−0.2007 (13)0.2212 (5)−0.0467 (2)0.057 (2)
H13−0.19260.2752−0.04960.068*
C14−0.5292 (11)0.2037 (5)−0.0674 (2)0.059 (2)
H14A−0.53350.2594−0.06140.071*
H14B−0.61910.1789−0.04800.071*
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)
H16−0.39050.2597−0.14370.083*
C17−0.5439 (10)0.2173 (4)−0.19497 (14)0.091 (4)
H17−0.48140.2426−0.21810.109*
C18−0.6919 (10)0.1692 (4)−0.20499 (17)0.106 (4)
H18−0.72830.1623−0.23480.127*
C19−0.7854 (8)0.1313 (4)−0.1705 (3)0.102 (4)
H19−0.88440.0991−0.17720.122*
C20−0.7310 (8)0.1416 (3)−0.1260 (2)0.071 (3)
H20−0.79350.1163−0.10290.086*
U11U22U33U12U13U23
Ni10.0249 (7)0.0408 (7)0.0363 (6)0.0012 (6)0.0032 (6)−0.0016 (5)
Cl10.0319 (11)0.0484 (11)0.0597 (9)−0.0045 (8)−0.0011 (8)−0.0002 (8)
N10.019 (3)0.050 (3)0.039 (3)0.001 (3)0.006 (3)−0.002 (2)
N20.044 (4)0.051 (4)0.046 (3)0.013 (3)0.008 (3)−0.004 (3)
N30.013 (3)0.069 (4)0.040 (3)0.007 (3)0.000 (3)0.006 (3)
N40.042 (4)0.053 (4)0.042 (3)0.026 (3)0.006 (3)0.005 (3)
C10.037 (5)0.068 (5)0.033 (3)0.007 (4)0.007 (3)0.005 (3)
C20.037 (5)0.072 (5)0.049 (4)0.014 (4)−0.001 (4)−0.008 (4)
C30.043 (5)0.081 (6)0.047 (4)−0.001 (4)−0.002 (4)−0.011 (4)
C40.059 (7)0.068 (6)0.060 (5)0.028 (4)0.024 (4)0.009 (4)
C50.033 (5)0.071 (6)0.040 (4)0.014 (4)0.001 (3)−0.005 (3)
C60.045 (6)0.084 (6)0.045 (4)0.019 (5)−0.004 (4)−0.004 (4)
C70.057 (7)0.161 (11)0.051 (5)0.022 (7)0.019 (5)0.012 (6)
C80.076 (10)0.147 (11)0.084 (7)0.005 (8)0.033 (7)0.047 (8)
C90.083 (9)0.077 (7)0.104 (7)−0.011 (6)−0.009 (7)0.026 (6)
C100.064 (7)0.080 (6)0.060 (5)0.005 (5)0.003 (5)0.000 (4)
C110.050 (5)0.059 (5)0.037 (3)0.012 (4)−0.007 (4)0.003 (3)
C120.031 (5)0.059 (5)0.054 (4)−0.009 (4)0.014 (4)0.005 (4)
C130.057 (6)0.056 (5)0.057 (4)−0.006 (4)−0.001 (4)0.003 (4)
C140.041 (6)0.085 (6)0.052 (4)0.029 (4)0.017 (4)0.011 (4)
C150.042 (5)0.052 (5)0.058 (4)0.013 (4)−0.002 (4)0.010 (3)
C160.072 (7)0.078 (6)0.057 (5)−0.003 (5)0.004 (5)0.014 (4)
C170.100 (10)0.128 (9)0.046 (5)0.016 (7)−0.010 (6)0.014 (5)
C180.119 (13)0.114 (10)0.086 (7)0.041 (8)−0.031 (8)−0.027 (6)
C190.073 (9)0.105 (9)0.127 (9)−0.011 (6)−0.012 (8)−0.035 (7)
C200.056 (7)0.059 (6)0.100 (7)−0.003 (5)0.009 (6)0.001 (5)
Ni1—N1i2.070 (5)C6—H60.9300
Ni1—N12.070 (5)C7—C81.320 (15)
Ni1—N32.140 (6)C7—H70.9300
Ni1—N3i2.140 (6)C8—C91.391 (15)
Ni1—Cl12.468 (2)C8—H80.9300
Ni1—Cl1i2.468 (2)C9—C101.392 (13)
N1—C11.310 (9)C9—H90.9300
N1—C21.365 (8)C10—H100.9300
N2—C11.345 (8)C11—H110.9300
N2—C31.358 (10)C12—C131.345 (11)
N2—C41.441 (9)C12—H120.9300
N3—C111.304 (9)C13—H130.9300
N3—C121.376 (8)C14—C151.512 (8)
N4—C111.333 (8)C14—H14A0.9700
N4—C131.373 (10)C14—H14B0.9700
N4—C141.436 (9)C15—C161.3900
C1—H10.9300C15—C201.3900
C2—C31.345 (10)C16—C171.3900
C2—H20.9300C16—H160.9300
C3—H30.9300C17—C181.3900
C4—C51.510 (10)C17—H170.9300
C4—H4A0.9700C18—C191.3900
C4—H4B0.9700C18—H180.9300
C5—C101.371 (10)C19—C201.3900
C5—C61.389 (9)C19—H190.9300
C6—C71.365 (13)C20—H200.9300
N1i—Ni1—N1180.0C5—C6—H6120.9
N1i—Ni1—N391.4 (2)C8—C7—C6124.0 (10)
N1—Ni1—N388.6 (2)C8—C7—H7118.0
N1i—Ni1—N3i88.6 (2)C6—C7—H7118.0
N1—Ni1—N3i91.4 (2)C7—C8—C9118.7 (10)
N3—Ni1—N3i180.0C7—C8—H8120.6
N1i—Ni1—Cl188.65 (16)C9—C8—H8120.6
N1—Ni1—Cl191.35 (16)C8—C9—C10119.4 (10)
N3—Ni1—Cl187.67 (17)C8—C9—H9120.3
N3i—Ni1—Cl192.33 (17)C10—C9—H9120.3
N1i—Ni1—Cl1i91.35 (16)C5—C10—C9120.0 (9)
N1—Ni1—Cl1i88.65 (16)C5—C10—H10120.0
N3—Ni1—Cl1i92.33 (17)C9—C10—H10120.0
N3i—Ni1—Cl1i87.67 (17)N3—C11—N4113.0 (7)
Cl1—Ni1—Cl1i180.0N3—C11—H11123.5
C1—N1—C2105.2 (6)N4—C11—H11123.5
C1—N1—Ni1126.6 (5)C13—C12—N3110.4 (8)
C2—N1—Ni1127.6 (5)C13—C12—H12124.8
C1—N2—C3106.3 (6)N3—C12—H12124.8
C1—N2—C4125.9 (7)C12—C13—N4105.7 (7)
C3—N2—C4127.6 (6)C12—C13—H13127.1
C11—N3—C12104.3 (6)N4—C13—H13127.1
C11—N3—Ni1128.4 (5)N4—C14—C15114.5 (6)
C12—N3—Ni1125.2 (5)N4—C14—H14A108.6
C11—N4—C13106.5 (7)C15—C14—H14A108.6
C11—N4—C14128.1 (7)N4—C14—H14B108.6
C13—N4—C14125.0 (7)C15—C14—H14B108.6
N1—C1—N2111.9 (6)H14A—C14—H14B107.6
N1—C1—H1124.1C16—C15—C20120.0
N2—C1—H1124.1C16—C15—C14120.0 (5)
C3—C2—N1109.8 (7)C20—C15—C14119.9 (5)
C3—C2—H2125.1C17—C16—C15120.0
N1—C2—H2125.1C17—C16—H16120.0
C2—C3—N2106.8 (6)C15—C16—H16120.0
C2—C3—H3126.6C18—C17—C16120.0
N2—C3—H3126.6C18—C17—H17120.0
N2—C4—C5114.1 (6)C16—C17—H17120.0
N2—C4—H4A108.7C17—C18—C19120.0
C5—C4—H4A108.7C17—C18—H18120.0
N2—C4—H4B108.7C19—C18—H18120.0
C5—C4—H4B108.7C20—C19—C18120.0
H4A—C4—H4B107.6C20—C19—H19120.0
C10—C5—C6119.6 (8)C18—C19—H19120.0
C10—C5—C4121.8 (7)C19—C20—C15120.0
C6—C5—C4118.5 (8)C19—C20—H20120.0
C7—C6—C5118.2 (9)C15—C20—H20120.0
C7—C6—H6120.9
N1i—Ni1—N1—C1−158 (20)N2—C4—C5—C10−40.6 (12)
N3—Ni1—N1—C135.5 (6)N2—C4—C5—C6142.2 (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—C7177.2 (8)
Cl1i—Ni1—N1—C1127.9 (6)C5—C6—C7—C8−2.4 (15)
N1i—Ni1—N1—C232 (22)C6—C7—C8—C93.8 (18)
N3—Ni1—N1—C2−135.0 (6)C7—C8—C9—C10−2.7 (18)
N3i—Ni1—N1—C245.0 (6)C6—C5—C10—C90.9 (13)
Cl1—Ni1—N1—C2137.4 (6)C4—C5—C10—C9−176.2 (9)
Cl1i—Ni1—N1—C2−42.6 (6)C8—C9—C10—C50.4 (16)
N1i—Ni1—N3—C1198.3 (6)C12—N3—C11—N41.1 (7)
N1—Ni1—N3—C11−81.7 (6)Ni1—N3—C11—N4165.0 (4)
N3i—Ni1—N3—C11−77 (56)C13—N4—C11—N3−1.2 (8)
Cl1—Ni1—N3—C119.8 (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—C1279.1 (5)N3—C12—C13—N4−0.1 (8)
N3i—Ni1—N3—C1284 (56)C11—N4—C13—C120.8 (8)
Cl1—Ni1—N3—C12170.5 (5)C14—N4—C13—C12174.2 (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—C15109.0 (8)
Ni1—N1—C1—N2−172.4 (4)N4—C14—C15—C16−66.5 (8)
C3—N2—C1—N10.4 (8)N4—C14—C15—C20116.2 (7)
C4—N2—C1—N1176.0 (7)C20—C15—C16—C170.0
C1—N1—C2—C3−0.2 (9)C14—C15—C16—C17−177.2 (5)
Ni1—N1—C2—C3171.9 (5)C15—C16—C17—C180.0
N1—C2—C3—N20.4 (10)C16—C17—C18—C190.0
C1—N2—C3—C2−0.5 (9)C17—C18—C19—C200.0
C4—N2—C3—C2−176.0 (7)C18—C19—C20—C150.0
C1—N2—C4—C5117.9 (8)C16—C15—C20—C190.0
C3—N2—C4—C5−67.5 (12)C14—C15—C20—C19177.2 (5)
D—H···AD—HH···AD···AD—H···A
C1—H1···Cl1ii0.932.773.617 (8)151
C14—H14B···Cl1ii0.972.683.579 (8)153
C13—H13···Cl1iii0.932.713.561 (9)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1—H1⋯Cl1i0.932.773.617 (8)151
C14—H14B⋯Cl1i0.972.683.579 (8)153
C13—H13⋯Cl1ii0.932.713.561 (9)152

Symmetry codes: (i) ; (ii) .

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