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Acta Cryst. (2008). E64, m787    [ doi:10.1107/S1600536808012968 ]

Bis{2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato-[kappa]2N,O}nickel(II) N,N-dimethylformamide disolvate

H. M. Ali, M. I. Mohamed Mustafa, M. R. Rizal and S. W. Ng

Abstract top

The Ni atom in the title compound, [Ni(C17H15N2O)2]·2C3H7NO, lies on a twofold rotation axis. It is N,O-chelated by the deprotonated Schiff base 2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolate ligand in a square-planar coordination environment. The molecule is linked to a solvent molecule by an indole-dimethylformamide N-H...O hydrogen bond.

Comment top

We have reported a number of metal complexes of Schiff bases derived from the condensation of salicylaldehyde and a biologically active primary amine. The structure of the presence Schiff base, has not been reported, but it is likely to exist as a zwitterion, 2-{[3-(1H-indol-3-yl)-propenyl]ammonio}phenolate as 2-{[3-(1H-Indol-3-yl)-propenyl]methylammonio}phenolate, synthesized from 2-(indol-3-yl)ethylamine and 2-hydroxy-5-methylacetophenone, exists in this form (Ali et al., 2007a, 2007b). The nickel derivative crystallizes from DMF as a disolvate (Scheme I, Fig. 1). The metal atom is N,O-chelated by the deprotonated Schiff base in a square planar coordination enviroment. The molecule is linked to the solvent molecule by an N–Hindole···ODMF hydrogen bond.

Related literature top

For the structures of Schiff bases derived from the consensation of 2-(indol-3-yl)ethylamine and other substituted salicylaldehydes, see: Ali et al. (2007a,b).

Experimental top

Tryptamine (0.30 g, 1.87 mmol) and salicylaldehyde (0.23 g, 1.86 mmol) were heated in ethanol (50 ml) for an hour. The solvent was removed to give the Schiff base. The ligand (0.49 g, 1.91 mmol) and nickel acetate tetrahydrate (0.23 g, 0.93 mmol) were reacted in ethanol (50 ml); several drops of triethylamine were also added. The solvent was removed and the product was recrystallized from DMF.

Refinement top

The carbon-bound H atoms were placed at calculated positions (C—H = 0.95–0.98 Å) and were included in the refinement in the riding-model approximation, with U(H) set to 1.2–1.5Ueq(C). The amino H atom also similarly generated [N—H = 0.88Å and U(H) = 1.2Ueq(N)].

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of Ni(C17H14N2O)2.2DMF; displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
Bis{2-[2-(1H-indol-3-yl)ethyliminomethyl]phenolato- κ2N,O}nickel(II) N,N-dimethylformamide disolvate top
Crystal data top
[Ni(C17H14N2O)2]·2C3H7NOF000 = 1544
Mr = 731.52Dx = 1.405 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2399 reflections
a = 38.927 (2) Åθ = 2.6–28.5º
b = 5.6999 (3) ŵ = 0.61 mm−1
c = 15.7560 (8) ÅT = 103 (2) K
β = 98.489 (2)ºPlate, yellow
V = 3457.6 (3) Å30.70 × 0.32 × 0.07 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		3875 independent reflections
Radiation source: medium-focus sealed tube2900 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 103(2) Kθmax = 27.5º
φ and ω scansθmin = 2.6º
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		h = −48→50
Tmin = 0.673, Tmax = 0.958k = −7→5
7704 measured reflectionsl = −19→20
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.133  w = 1/[σ2(Fo2) + (0.0586P)2 + 9.176P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3875 reflectionsΔρmax = 0.82 e Å−3
234 parametersΔρmin = −0.48 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C17H14N2O)2]·2C3H7NOV = 3457.6 (3) Å3
Mr = 731.52Z = 4
Monoclinic, C2/cMo Kα
a = 38.927 (2) ŵ = 0.61 mm−1
b = 5.6999 (3) ÅT = 103 (2) K
c = 15.7560 (8) Å0.70 × 0.32 × 0.07 mm
β = 98.489 (2)º
Data collection top
Bruker APEXII
diffractometer		3875 independent reflections
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		2900 reflections with I > 2σ(I)
Tmin = 0.673, Tmax = 0.958Rint = 0.030
7704 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048234 parameters
wR(F2) = 0.133H-atom parameters constrained
S = 1.03Δρmax = 0.82 e Å−3
3875 reflectionsΔρmin = −0.48 e Å−3
Special details top

Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.25000.75000.50000.01379 (15)
O10.27749 (5)0.8616 (4)0.42443 (12)0.0208 (5)
O20.08509 (9)−0.4015 (5)0.56375 (17)0.0564 (9)
N10.23434 (6)0.4881 (4)0.42765 (14)0.0151 (5)
N30.11380 (6)−0.0268 (5)0.48184 (16)0.0224 (6)
H3N0.1102−0.15700.50920.027*
N40.06308 (7)−0.7205 (4)0.62051 (16)0.0215 (5)
C10.29181 (7)0.7412 (5)0.36804 (16)0.0169 (5)
C20.32195 (8)0.8312 (5)0.34033 (17)0.0199 (6)
H20.33110.97760.36180.024*
C30.33829 (8)0.7079 (5)0.28206 (18)0.0215 (6)
H30.35890.76880.26500.026*
C40.32486 (8)0.4956 (6)0.24797 (18)0.0229 (6)
H40.33600.41390.20710.027*
C50.29539 (8)0.4055 (5)0.27382 (17)0.0202 (6)
H50.28600.26180.25010.024*
C60.27889 (7)0.5234 (5)0.33495 (17)0.0168 (6)
C70.24926 (7)0.4181 (5)0.36379 (16)0.0165 (6)
H70.23960.28420.33320.020*
C80.20526 (7)0.3382 (5)0.44577 (18)0.0169 (6)
H8A0.20870.29980.50770.020*
H8B0.20580.18920.41370.020*
C90.16973 (7)0.4520 (5)0.42173 (17)0.0171 (6)
H9A0.16830.59440.45700.021*
H9B0.16660.49970.36070.021*
C100.14497 (8)0.0886 (5)0.48646 (19)0.0211 (6)
H100.16600.03880.52010.025*
C110.14169 (7)0.2850 (5)0.43600 (17)0.0175 (6)
C120.10598 (7)0.2930 (5)0.39755 (17)0.0175 (6)
C130.08600 (8)0.4471 (6)0.34154 (18)0.0229 (7)
H130.09640.58070.31970.028*
C140.05115 (8)0.4034 (6)0.31834 (19)0.0286 (7)
H140.03750.50910.28080.034*
C150.03524 (8)0.2044 (6)0.3492 (2)0.0283 (8)
H150.01110.17790.33190.034*
C160.05416 (8)0.0488 (6)0.40391 (19)0.0249 (7)
H160.0435−0.08510.42480.030*
C170.08943 (8)0.0937 (5)0.42782 (17)0.0192 (6)
C180.08801 (10)−0.5798 (7)0.6027 (2)0.0379 (9)
H180.1111−0.62750.62370.045*
C190.02741 (10)−0.6713 (8)0.5891 (3)0.0472 (10)
H19A0.0258−0.52570.55570.071*
H19B0.0145−0.65370.63760.071*
H19C0.0175−0.80080.55250.071*
C200.07081 (13)−0.9334 (7)0.6694 (3)0.0521 (11)
H20A0.0960−0.95030.68440.078*
H20B0.0615−1.06840.63500.078*
H20C0.0602−0.92580.72200.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0150 (3)0.0131 (3)0.0133 (2)−0.0029 (2)0.00219 (17)−0.0008 (2)
O10.0248 (11)0.0184 (11)0.0203 (10)−0.0039 (9)0.0075 (8)−0.0011 (9)
O20.105 (3)0.0285 (15)0.0453 (15)−0.0269 (16)0.0436 (16)−0.0058 (13)
N10.0133 (12)0.0132 (12)0.0182 (11)−0.0002 (9)−0.0001 (9)0.0026 (9)
N30.0214 (13)0.0202 (13)0.0256 (13)−0.0042 (11)0.0038 (10)0.0072 (11)
N40.0240 (13)0.0171 (13)0.0244 (12)−0.0027 (11)0.0074 (10)0.0012 (10)
C10.0200 (14)0.0164 (13)0.0135 (12)0.0025 (13)−0.0003 (10)0.0036 (12)
C20.0231 (15)0.0189 (14)0.0174 (13)−0.0020 (12)0.0025 (11)0.0020 (11)
C30.0193 (14)0.0256 (17)0.0199 (13)0.0008 (12)0.0042 (11)0.0095 (12)
C40.0265 (16)0.0245 (16)0.0186 (13)0.0070 (13)0.0063 (12)0.0017 (12)
C50.0252 (16)0.0189 (15)0.0163 (13)0.0008 (12)0.0025 (11)−0.0004 (11)
C60.0179 (14)0.0167 (14)0.0154 (12)0.0020 (12)0.0015 (10)0.0022 (11)
C70.0180 (14)0.0171 (14)0.0128 (12)0.0009 (11)−0.0027 (10)0.0005 (11)
C80.0168 (14)0.0147 (13)0.0191 (13)−0.0041 (11)0.0023 (11)−0.0006 (11)
C90.0178 (14)0.0170 (14)0.0163 (13)−0.0013 (12)0.0019 (10)0.0017 (11)
C100.0183 (15)0.0207 (15)0.0242 (14)−0.0010 (12)0.0027 (11)0.0032 (12)
C110.0192 (14)0.0176 (15)0.0161 (12)−0.0006 (11)0.0039 (10)−0.0022 (11)
C120.0204 (14)0.0193 (15)0.0136 (12)−0.0013 (11)0.0052 (10)−0.0027 (11)
C130.0233 (16)0.0268 (17)0.0184 (14)0.0003 (13)0.0020 (12)0.0017 (12)
C140.0201 (16)0.042 (2)0.0217 (14)0.0034 (14)−0.0018 (12)0.0025 (14)
C150.0197 (15)0.040 (2)0.0250 (15)−0.0045 (14)0.0029 (12)−0.0057 (14)
C160.0205 (16)0.0300 (18)0.0255 (15)−0.0066 (13)0.0074 (12)−0.0040 (13)
C170.0198 (15)0.0189 (15)0.0195 (13)−0.0034 (12)0.0050 (11)−0.0020 (12)
C180.043 (2)0.037 (2)0.0393 (19)−0.0171 (17)0.0231 (16)−0.0175 (17)
C190.029 (2)0.064 (3)0.047 (2)−0.0047 (19)0.0017 (17)−0.010 (2)
C200.081 (3)0.032 (2)0.045 (2)0.012 (2)0.016 (2)0.0071 (19)
Geometric parameters (Å, °) top
Ni1—O1i1.829 (2)C8—C91.524 (4)
Ni1—O11.829 (2)C8—H8A0.9900
Ni1—N1i1.922 (2)C8—H8B0.9900
Ni1—N11.922 (2)C9—C111.490 (4)
O1—C11.310 (3)C9—H9A0.9900
O2—C181.184 (5)C9—H9B0.9900
N1—C71.297 (3)C10—C111.368 (4)
N1—C81.479 (3)C10—H100.9500
N3—C171.363 (4)C11—C121.433 (4)
N3—C101.373 (4)C12—C131.397 (4)
N3—H3N0.8800C12—C171.423 (4)
N4—C181.320 (4)C13—C141.375 (4)
N4—C191.431 (4)C13—H130.9500
N4—C201.445 (4)C14—C151.412 (5)
C1—C21.408 (4)C14—H140.9500
C1—C61.410 (4)C15—C161.373 (5)
C2—C31.383 (4)C15—H150.9500
C2—H20.9500C16—C171.393 (4)
C3—C41.394 (4)C16—H160.9500
C3—H30.9500C18—H180.9500
C4—C51.372 (4)C19—H19A0.9800
C4—H40.9500C19—H19B0.9800
C5—C61.405 (4)C19—H19C0.9800
C5—H50.9500C20—H20A0.9800
C6—C71.432 (4)C20—H20B0.9800
C7—H70.9500C20—H20C0.9800
O1i—Ni1—O1180.00 (10)C11—C9—H9A109.6
O1i—Ni1—N1i92.81 (9)C8—C9—H9A109.6
O1—Ni1—N1i87.19 (9)C11—C9—H9B109.6
O1i—Ni1—N187.19 (9)C8—C9—H9B109.6
O1—Ni1—N192.81 (9)H9A—C9—H9B108.1
N1i—Ni1—N1180.000 (1)C11—C10—N3110.8 (3)
C1—O1—Ni1127.41 (19)C11—C10—H10124.6
C7—N1—C8114.6 (2)N3—C10—H10124.6
C7—N1—Ni1124.0 (2)C10—C11—C12105.9 (2)
C8—N1—Ni1121.26 (17)C10—C11—C9127.1 (3)
C17—N3—C10108.6 (2)C12—C11—C9127.0 (2)
C17—N3—H3N125.7C13—C12—C17118.4 (3)
C10—N3—H3N125.7C13—C12—C11134.6 (3)
C18—N4—C19120.9 (3)C17—C12—C11107.0 (2)
C18—N4—C20121.4 (3)C14—C13—C12119.3 (3)
C19—N4—C20117.6 (3)C14—C13—H13120.3
O1—C1—C2118.5 (3)C12—C13—H13120.3
O1—C1—C6123.2 (2)C13—C14—C15121.3 (3)
C2—C1—C6118.3 (3)C13—C14—H14119.3
C3—C2—C1120.4 (3)C15—C14—H14119.3
C3—C2—H2119.8C16—C15—C14120.9 (3)
C1—C2—H2119.8C16—C15—H15119.6
C2—C3—C4120.9 (3)C14—C15—H15119.6
C2—C3—H3119.5C15—C16—C17117.9 (3)
C4—C3—H3119.5C15—C16—H16121.1
C5—C4—C3119.5 (3)C17—C16—H16121.1
C5—C4—H4120.2N3—C17—C16130.1 (3)
C3—C4—H4120.2N3—C17—C12107.7 (3)
C4—C5—C6120.7 (3)C16—C17—C12122.2 (3)
C4—C5—H5119.6O2—C18—N4127.9 (4)
C6—C5—H5119.6O2—C18—H18116.1
C5—C6—C1120.0 (3)N4—C18—H18116.1
C5—C6—C7119.2 (3)N4—C19—H19A109.5
C1—C6—C7120.8 (2)N4—C19—H19B109.5
N1—C7—C6126.2 (3)H19A—C19—H19B109.5
N1—C7—H7116.9N4—C19—H19C109.5
C6—C7—H7116.9H19A—C19—H19C109.5
N1—C8—C9113.5 (2)H19B—C19—H19C109.5
N1—C8—H8A108.9N4—C20—H20A109.5
C9—C8—H8A108.9N4—C20—H20B109.5
N1—C8—H8B108.9H20A—C20—H20B109.5
C9—C8—H8B108.9N4—C20—H20C109.5
H8A—C8—H8B107.7H20A—C20—H20C109.5
C11—C9—C8110.4 (2)H20B—C20—H20C109.5
N1i—Ni1—O1—C1153.4 (2)N1—C8—C9—C11176.0 (2)
N1—Ni1—O1—C1−26.6 (2)C17—N3—C10—C110.0 (3)
O1i—Ni1—N1—C7−164.6 (2)N3—C10—C11—C120.2 (3)
O1—Ni1—N1—C715.4 (2)N3—C10—C11—C9−178.0 (3)
O1i—Ni1—N1—C810.6 (2)C8—C9—C11—C1019.2 (4)
O1—Ni1—N1—C8−169.4 (2)C8—C9—C11—C12−158.7 (3)
Ni1—O1—C1—C2−155.2 (2)C10—C11—C12—C13179.0 (3)
Ni1—O1—C1—C623.5 (4)C9—C11—C12—C13−2.8 (5)
O1—C1—C2—C3178.8 (3)C10—C11—C12—C17−0.3 (3)
C6—C1—C2—C30.0 (4)C9—C11—C12—C17177.9 (3)
C1—C2—C3—C41.6 (4)C17—C12—C13—C140.8 (4)
C2—C3—C4—C5−1.3 (4)C11—C12—C13—C14−178.5 (3)
C3—C4—C5—C6−0.8 (4)C12—C13—C14—C15−0.7 (5)
C4—C5—C6—C12.4 (4)C13—C14—C15—C160.4 (5)
C4—C5—C6—C7−176.7 (3)C14—C15—C16—C170.0 (4)
O1—C1—C6—C5179.3 (3)C10—N3—C17—C16−178.7 (3)
C2—C1—C6—C5−2.0 (4)C10—N3—C17—C12−0.2 (3)
O1—C1—C6—C7−1.6 (4)C15—C16—C17—N3178.4 (3)
C2—C1—C6—C7177.1 (3)C15—C16—C17—C120.1 (4)
C8—N1—C7—C6−177.0 (3)C13—C12—C17—N3−179.1 (2)
Ni1—N1—C7—C6−1.5 (4)C11—C12—C17—N30.3 (3)
C5—C6—C7—N1169.8 (3)C13—C12—C17—C16−0.4 (4)
C1—C6—C7—N1−9.3 (4)C11—C12—C17—C16179.0 (3)
C7—N1—C8—C9−108.6 (3)C19—N4—C18—O22.6 (5)
Ni1—N1—C8—C975.7 (3)C20—N4—C18—O2−179.7 (3)
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O20.881.972.811 (3)159
Table 1
Selected geometric parameters (Å) top
Ni1—O11.829 (2)Ni1—N11.922 (2)
Acknowledgements top

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02–03–2031) for supporting this study.

references
References top

Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007a). Acta Cryst. E63, o3458–?.

Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007b). Acta Cryst. E63, o1729–o1730.

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

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

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

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.