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Acta Cryst. (2007). E63, m3033    [ doi:10.1107/S1600536807056966 ]

Bis{2'-[(5-chloro-1H-3-indolyl)methylene]-2-(1H-3-indolyl)acetohydrazido-[kappa]2N,O}nickel(II) dimethyl sulfoxide disolvate

H. M. Ali, S. J. Nazzatush, M. R. Rizal and S. W. Ng

Abstract top

The Ni atom in the title compound, [Ni(C19H14ClN4O)2]·2C2H6OS, which lies on a centre of inversion, is N,O-chelated by the two monoanionic ligands in a square-planar geometry. The asymmetric unit also contains a dimethyl sulfoxide solvent molecule. The donor amino sites of the metal-bearing molecule interact with the solvent molecules to furnish a hydrogen-bonded layer structure.

Related literature top

For the structure of 2'-[(5-chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide, see Ali et al. (2007).

Experimental top

2'-[(5-Chloro-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide was synthesized by using a reported procedure (Ali et al., 2007). This compound (1 g, 2.85 mmol) and nickel acetate tetrahydrate (0.35 g, 1.42 mmol) were heated in ethanol (50 ml) for 5 h. The product that separated was collected and recrystallized from DMSO.

Refinement top

Carbon-bound H atoms were placed at calculated positions (C–H 0.95–0.99 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2–1.5Ueq(C). The amino hydrogen atom was located in a difference Fouier map, and was refined with a distance restraint of N–H 0.88±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of (C19H14ClN4OS)2Ni.2DMSO. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are shown as spheres of arbitrary radii. [Symmetry code (i): 1 – x, 1 – y, 1 – z.]
Bis{2'-[(5-chloro-1H-3-indolyl)methylene]-2-(1H-3- indolyl)acetohydrazido-κ2N,O}nickel(II) dimethyl sulfoxide disolvate top
Crystal data top
[Ni(C19H14ClN4O)2]·2C2H6OSF000 = 948
Mr = 914.55Dx = 1.484 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1360 reflections
a = 11.659 (1) Åθ = 4.4–22.5º
b = 10.219 (1) ŵ = 0.76 mm−1
c = 17.585 (2) ÅT = 139 (2) K
β = 102.272 (3)ºBlock, red
V = 2047.2 (3) Å30.42 × 0.05 × 0.02 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer		4683 independent reflections
Radiation source: medium-focus sealed tube2216 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.108
T = 139(2) Kθmax = 27.5º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→14
Tmin = 0.776, Tmax = 0.985k = −13→10
13220 measured reflectionsl = −22→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.198  w = 1/[σ2(Fo2) + (0.076P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
4683 reflectionsΔρmax = 0.50 e Å−3
278 parametersΔρmin = −0.89 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ni(C19H14ClN4O)2]·2C2H6OSV = 2047.2 (3) Å3
Mr = 914.55Z = 2
Monoclinic, P21/cMo Kα
a = 11.659 (1) ŵ = 0.76 mm−1
b = 10.219 (1) ÅT = 139 (2) K
c = 17.585 (2) Å0.42 × 0.05 × 0.02 mm
β = 102.272 (3)º
Data collection top
Bruker APEXII CCD
diffractometer		4683 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2216 reflections with I > 2σ(I)
Tmin = 0.776, Tmax = 0.985Rint = 0.108
13220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0492 restraints
wR(F2) = 0.198H atoms treated by a mixture of
independent and constrained refinement
S = 0.99Δρmax = 0.50 e Å−3
4683 reflectionsΔρmin = −0.89 e Å−3
278 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.0207 (3)
Cl10.77582 (14)−0.23758 (13)0.53762 (9)0.0329 (4)
S10.21730 (14)−0.18848 (14)0.10978 (9)0.0305 (4)
O10.3902 (3)0.5808 (3)0.4234 (2)0.0240 (9)
O20.2384 (3)−0.0989 (4)0.1797 (2)0.0315 (10)
N10.4210 (4)−0.0021 (5)0.2925 (3)0.0263 (11)
H1N0.369 (4)−0.029 (6)0.252 (2)0.05 (2)*
N20.4846 (4)0.3641 (4)0.4281 (3)0.0214 (10)
N30.4110 (4)0.3933 (4)0.3554 (3)0.0242 (11)
N4−0.0266 (5)0.5368 (5)0.3064 (3)0.0289 (12)
H4N−0.096 (2)0.499 (5)0.297 (4)0.040 (19)*
C10.5565 (5)0.0105 (5)0.4043 (3)0.0207 (12)
C20.6428 (5)−0.0401 (5)0.4652 (3)0.0230 (13)
H20.67870.01310.50790.028*
C30.6737 (5)−0.1689 (5)0.4610 (3)0.0262 (14)
C40.6230 (5)−0.2500 (5)0.3983 (3)0.0276 (14)
H40.6474−0.33860.39760.033*
C50.5385 (5)−0.2023 (5)0.3380 (3)0.0276 (14)
H50.5041−0.25600.29500.033*
C60.5055 (5)−0.0719 (5)0.3425 (3)0.0230 (13)
C70.4171 (5)0.1210 (5)0.3197 (3)0.0240 (13)
H70.36570.18770.29500.029*
C80.4989 (5)0.1359 (5)0.3887 (3)0.0237 (13)
C90.5233 (5)0.2449 (5)0.4401 (3)0.0226 (13)
H90.57390.22850.48910.027*
C100.3674 (5)0.5089 (5)0.3609 (3)0.0223 (12)
C110.2836 (5)0.5632 (5)0.2906 (3)0.0243 (13)
H11A0.31270.64950.27740.029*
H11B0.28200.50410.24580.029*
C120.1612 (5)0.5787 (5)0.3033 (3)0.0224 (13)
C130.0737 (5)0.4888 (5)0.2867 (3)0.0252 (13)
H130.08060.40490.26480.030*
C140.1126 (5)0.6907 (5)0.3346 (3)0.0211 (12)
C150.1571 (5)0.8133 (5)0.3635 (3)0.0267 (14)
H150.23510.83790.36200.032*
C160.0856 (6)0.8971 (6)0.3938 (3)0.0331 (16)
H160.11520.97990.41340.040*
C17−0.0294 (6)0.8624 (5)0.3964 (3)0.0315 (15)
H17−0.07610.92120.41870.038*
C18−0.0766 (6)0.7439 (5)0.3671 (3)0.0291 (14)
H18−0.15540.72080.36750.035*
C19−0.0038 (5)0.6605 (5)0.3371 (3)0.0233 (13)
C200.1682 (6)−0.0854 (6)0.0285 (4)0.0445 (18)
H20A0.2345−0.03450.01820.067*
H20B0.1080−0.02570.03960.067*
H20C0.1349−0.1388−0.01710.067*
C210.0809 (6)−0.2677 (6)0.1102 (4)0.0408 (17)
H21A0.0888−0.32140.15720.061*
H21B0.0593−0.32360.06410.061*
H21C0.0198−0.20170.10950.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0197 (6)0.0166 (5)0.0232 (6)0.0004 (4)−0.0016 (4)−0.0016 (4)
Cl10.0278 (9)0.0262 (8)0.0419 (9)0.0053 (6)0.0011 (7)0.0021 (6)
S10.0267 (9)0.0282 (8)0.0343 (9)0.0030 (7)0.0017 (7)−0.0093 (7)
O10.024 (2)0.0199 (19)0.025 (2)0.0006 (17)−0.0017 (18)0.0009 (16)
O20.023 (2)0.037 (2)0.029 (2)−0.0041 (19)−0.0044 (19)−0.0139 (18)
N10.026 (3)0.026 (3)0.024 (3)−0.004 (2)−0.002 (2)−0.007 (2)
N20.016 (3)0.023 (2)0.025 (3)−0.002 (2)0.003 (2)−0.0009 (19)
N30.025 (3)0.021 (2)0.023 (3)0.001 (2)−0.003 (2)0.0013 (19)
N40.023 (3)0.027 (3)0.036 (3)−0.006 (2)0.002 (2)−0.001 (2)
C10.019 (3)0.018 (3)0.025 (3)−0.004 (2)0.004 (2)−0.005 (2)
C20.018 (3)0.025 (3)0.025 (3)−0.005 (2)0.000 (3)−0.005 (2)
C30.023 (3)0.023 (3)0.033 (3)0.000 (2)0.006 (3)0.001 (2)
C40.028 (4)0.017 (3)0.041 (4)−0.001 (3)0.013 (3)−0.006 (3)
C50.024 (3)0.025 (3)0.033 (3)−0.009 (3)0.005 (3)−0.010 (3)
C60.015 (3)0.027 (3)0.024 (3)−0.004 (2)−0.001 (3)0.000 (2)
C70.026 (3)0.022 (3)0.023 (3)−0.006 (2)0.001 (3)−0.001 (2)
C80.025 (3)0.021 (3)0.023 (3)−0.002 (2)0.001 (3)−0.004 (2)
C90.022 (3)0.019 (3)0.025 (3)−0.002 (2)0.003 (3)0.000 (2)
C100.017 (3)0.027 (3)0.021 (3)−0.004 (2)−0.001 (2)0.002 (2)
C110.024 (3)0.025 (3)0.021 (3)0.003 (3)−0.003 (3)0.000 (2)
C120.023 (3)0.022 (3)0.019 (3)0.000 (2)−0.002 (3)0.004 (2)
C130.023 (3)0.024 (3)0.027 (3)0.001 (3)0.002 (3)0.002 (2)
C140.021 (3)0.021 (3)0.018 (3)−0.002 (2)−0.001 (2)0.005 (2)
C150.026 (3)0.024 (3)0.026 (3)−0.003 (3)−0.003 (3)0.004 (2)
C160.041 (4)0.022 (3)0.032 (4)−0.002 (3)−0.002 (3)0.001 (3)
C170.034 (4)0.028 (3)0.033 (4)0.010 (3)0.007 (3)0.003 (3)
C180.024 (3)0.031 (3)0.031 (3)0.002 (3)0.003 (3)0.007 (3)
C190.026 (3)0.020 (3)0.022 (3)−0.002 (2)0.001 (3)0.006 (2)
C200.058 (5)0.044 (4)0.030 (4)−0.012 (4)0.007 (4)−0.003 (3)
C210.042 (4)0.040 (4)0.036 (4)−0.017 (3)−0.001 (3)−0.001 (3)
Geometric parameters (Å, °) top
Ni1—O11.845 (4)C7—C81.382 (7)
Ni1—O1i1.845 (4)C7—H70.9500
Ni1—N2i1.861 (4)C8—C91.425 (7)
Ni1—N21.861 (4)C9—H90.9500
Cl1—C31.745 (6)C10—C111.510 (7)
S1—O21.510 (4)C11—C121.499 (8)
S1—C201.769 (6)C11—H11A0.9900
S1—C211.786 (6)C11—H11B0.9900
O1—C101.301 (6)C12—C131.358 (7)
N1—C71.351 (6)C12—C141.438 (7)
N1—C61.372 (7)C13—H130.9500
N1—H1N0.88 (4)C14—C191.402 (8)
N2—C91.300 (6)C14—C151.408 (7)
N2—N31.413 (6)C15—C161.379 (8)
N3—C101.297 (6)C15—H150.9500
N4—C191.378 (7)C16—C171.398 (8)
N4—C131.378 (7)C16—H160.9500
N4—H4N0.88 (3)C17—C181.383 (8)
C1—C21.403 (7)C17—H170.9500
C1—C61.403 (7)C18—C191.384 (8)
C1—C81.446 (7)C18—H180.9500
C2—C31.370 (7)C20—H20A0.9800
C2—H20.9500C20—H20B0.9800
C3—C41.405 (8)C20—H20C0.9800
C4—C51.374 (8)C21—H21A0.9800
C4—H40.9500C21—H21B0.9800
C5—C61.395 (7)C21—H21C0.9800
C5—H50.9500
O1—Ni1—O1i180.000 (1)C8—C9—H9116.1
O1—Ni1—N2i96.52 (17)N3—C10—O1124.4 (5)
O1i—Ni1—N2i83.48 (17)N3—C10—C11118.0 (5)
O1—Ni1—N283.48 (17)O1—C10—C11117.6 (5)
O1i—Ni1—N296.52 (17)C12—C11—C10112.9 (5)
N2i—Ni1—N2180.000 (1)C12—C11—H11A109.0
O2—S1—C20105.4 (3)C10—C11—H11A109.0
O2—S1—C21105.2 (3)C12—C11—H11B109.0
C20—S1—C2197.9 (3)C10—C11—H11B109.0
C10—O1—Ni1110.4 (3)H11A—C11—H11B107.8
C7—N1—C6109.3 (5)C13—C12—C14106.4 (5)
C7—N1—H1N121 (4)C13—C12—C11126.3 (5)
C6—N1—H1N129 (4)C14—C12—C11127.3 (5)
C9—N2—N3117.9 (4)C12—C13—N4110.1 (5)
C9—N2—Ni1127.5 (4)C12—C13—H13124.9
N3—N2—Ni1114.2 (3)N4—C13—H13124.9
C10—N3—N2107.2 (4)C19—C14—C15118.0 (5)
C19—N4—C13108.8 (5)C19—C14—C12107.4 (5)
C19—N4—H4N125 (4)C15—C14—C12134.6 (5)
C13—N4—H4N126 (4)C16—C15—C14119.1 (6)
C2—C1—C6119.1 (5)C16—C15—H15120.5
C2—C1—C8134.5 (5)C14—C15—H15120.5
C6—C1—C8106.3 (5)C15—C16—C17121.2 (6)
C3—C2—C1117.8 (5)C15—C16—H16119.4
C3—C2—H2121.1C17—C16—H16119.4
C1—C2—H2121.1C18—C17—C16121.2 (6)
C2—C3—C4122.5 (5)C18—C17—H17119.4
C2—C3—Cl1119.3 (4)C16—C17—H17119.4
C4—C3—Cl1118.2 (4)C17—C18—C19117.0 (6)
C5—C4—C3120.6 (5)C17—C18—H18121.5
C5—C4—H4119.7C19—C18—H18121.5
C3—C4—H4119.7N4—C19—C18129.2 (6)
C4—C5—C6117.1 (5)N4—C19—C14107.3 (5)
C4—C5—H5121.4C18—C19—C14123.5 (5)
C6—C5—H5121.4S1—C20—H20A109.5
N1—C6—C5129.0 (5)S1—C20—H20B109.5
N1—C6—C1108.2 (5)H20A—C20—H20B109.5
C5—C6—C1122.8 (5)S1—C20—H20C109.5
N1—C7—C8110.2 (5)H20A—C20—H20C109.5
N1—C7—H7124.9H20B—C20—H20C109.5
C8—C7—H7124.9S1—C21—H21A109.5
C7—C8—C9130.6 (5)S1—C21—H21B109.5
C7—C8—C1105.9 (5)H21A—C21—H21B109.5
C9—C8—C1123.4 (5)S1—C21—H21C109.5
N2—C9—C8127.8 (5)H21A—C21—H21C109.5
N2—C9—H9116.1H21B—C21—H21C109.5
N2i—Ni1—O1—C10175.5 (4)Ni1—N2—C9—C8170.9 (5)
N2—Ni1—O1—C10−4.5 (4)C7—C8—C9—N2−10.9 (11)
O1—Ni1—N2—C9−167.7 (5)C1—C8—C9—N2173.1 (6)
O1i—Ni1—N2—C912.3 (5)N2—N3—C10—O10.0 (7)
O1—Ni1—N2—N34.7 (3)N2—N3—C10—C11−179.2 (4)
O1i—Ni1—N2—N3−175.3 (3)Ni1—O1—C10—N33.8 (7)
C9—N2—N3—C10169.3 (5)Ni1—O1—C10—C11−177.0 (4)
Ni1—N2—N3—C10−3.8 (5)N3—C10—C11—C12113.6 (6)
C6—C1—C2—C30.3 (8)O1—C10—C11—C12−65.7 (6)
C8—C1—C2—C3177.8 (6)C10—C11—C12—C13−91.7 (7)
C1—C2—C3—C40.5 (9)C10—C11—C12—C1488.7 (7)
C1—C2—C3—Cl1−177.1 (4)C14—C12—C13—N4−0.6 (6)
C2—C3—C4—C5−0.4 (9)C11—C12—C13—N4179.8 (5)
Cl1—C3—C4—C5177.3 (5)C19—N4—C13—C12−0.5 (6)
C3—C4—C5—C6−0.6 (9)C13—C12—C14—C191.4 (6)
C7—N1—C6—C5179.2 (6)C11—C12—C14—C19−178.9 (5)
C7—N1—C6—C10.5 (7)C13—C12—C14—C15178.9 (6)
C4—C5—C6—N1−177.1 (6)C11—C12—C14—C15−1.4 (10)
C4—C5—C6—C11.4 (9)C19—C14—C15—C161.0 (8)
C2—C1—C6—N1177.5 (5)C12—C14—C15—C16−176.3 (6)
C8—C1—C6—N1−0.7 (6)C14—C15—C16—C170.0 (8)
C2—C1—C6—C5−1.3 (9)C15—C16—C17—C18−1.4 (9)
C8—C1—C6—C5−179.4 (5)C16—C17—C18—C191.6 (8)
C6—N1—C7—C8−0.2 (7)C13—N4—C19—C18−177.5 (5)
N1—C7—C8—C9−176.8 (6)C13—N4—C19—C141.4 (6)
N1—C7—C8—C1−0.2 (7)C17—C18—C19—N4178.2 (5)
C2—C1—C8—C7−177.2 (6)C17—C18—C19—C14−0.5 (8)
C6—C1—C8—C70.6 (6)C15—C14—C19—N4−179.7 (5)
C2—C1—C8—C9−0.3 (10)C12—C14—C19—N4−1.7 (6)
C6—C1—C8—C9177.4 (5)C15—C14—C19—C18−0.8 (8)
N3—N2—C9—C8−1.3 (9)C12—C14—C19—C18177.3 (5)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.88 (4)1.90 (5)2.766 (6)167 (6)
N4—H4N···O2ii0.88 (3)2.05 (3)2.887 (6)158 (6)
Symmetry codes: (ii) −x, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å) top
Ni1—O11.845 (4)Ni1—N21.861 (4)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O20.88 (4)1.90 (5)2.766 (6)167 (6)
N4—H4N···O2i0.88 (3)2.05 (3)2.887 (6)158 (6)
Symmetry codes: (i) −x, y+1/2, −z+1/2.
Acknowledgements top

The authors thank the University of Canterbury for the diffraction measurements, and the Science Fund (grant No. 12–02-03–2031) and the Fundamental Research Grant Scheme (grant No·FP064/2006 A) for supporting this study.

references
References top

Ali, H. M., Nazzatush Shimar, J., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1807–o1808.

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Westrip, S. P. (2007). publCIF. In preparation.