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Acta Cryst. (2007). E63, m2012    [ doi:10.1107/S1600536807030930 ]

Azido{2-[2-(piperidin-1-yl)ethyliminomethyl]-1-naphtholato}nickel(II)

Z. Zhou and Z.-H. Xiao

Abstract top

The title compound, [Ni(C18H21N2O)(N3)], was obtained by the reaction of the Schiff base ligand 2-[2-(piperidin-1-yl)ethyliminomethyl]-1-naphthol with sodium azide and nickel(II) nitrate in methanol solution. The Ni atom is four-coordinated by the N,N,O-donor set of the Schiff base ligand and by the terminal N atom of the azide group, forming a square-planar geometry. The piperidine ring adopts a chair conformation and lies nearly perpendicular to the naphthalene system.

Comment top

The title compound, (I) (Fig. 1), is a mononuclear nickel(II) complex. The Ni atom is four-coordinated by the NNO donor set of the Schiff base ligand and by the terminal N atom of the azide group, forming a square planar geometry. The piperidine ring adopts chair conformation and lies nearly perpendicular to the naphthalene ring. The bond lengths and bond angles subtended at the metal centre are comparable to the values in other similar nickel(II) complexes (Zhu et al., 2004; Peng et al., 2006; Liu et al., 2006; Sun et al., 2005; Skovsgaard et al., 2005).

Related literature top

For related literature, see: Zhu et al. (2004); Peng et al. (2006); Liu et al. (2006); Sun et al. (2005); Skovsgaard et al. (2005).

Experimental top

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg), 2-piperidin-1-ylethylamine (0.1 mmol, 12.8 mg), sodium azide (0.1 mmol, 6.5 mg) and nickel nitrate (0.1 mmol, 29.1 mg) were mixed in a methanol solution (10 ml). The mixture was stirred at room temperature for 30 min to give an orange solution. Red block-like crystals were formed by slow evaporation of the solution in air.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Azido{2-[2-(piperidin-1-yl)ethyliminomethyl]-1-naphtholato}nickel(II) top
Crystal data top
[Ni(C18H21N2O)(N3)]F000 = 1600
Mr = 382.11Dx = 1.498 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2636 reflections
a = 7.5298 (12) Åθ = 2.4–24.9º
b = 13.268 (2) ŵ = 1.16 mm−1
c = 33.912 (5) ÅT = 298 (2) K
V = 3387.9 (9) Å3Block, red
Z = 80.27 × 0.23 × 0.22 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer		3886 independent reflections
Radiation source: fine-focus sealed tube2511 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.057
T = 298(2) Kθmax = 27.5º
ω scansθmin = 2.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −9→9
Tmin = 0.744, Tmax = 0.784k = −17→9
19025 measured reflectionsl = −42→44
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.097  w = 1/[σ2(Fo2) + (0.0408P)2 + 0.3939P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3886 reflectionsΔρmax = 0.31 e Å−3
226 parametersΔρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C18H21N2O)(N3)]V = 3387.9 (9) Å3
Mr = 382.11Z = 8
Orthorhombic, PbcaMo Kα
a = 7.5298 (12) ŵ = 1.16 mm−1
b = 13.268 (2) ÅT = 298 (2) K
c = 33.912 (5) Å0.27 × 0.23 × 0.22 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer		3886 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2511 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.784Rint = 0.057
19025 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039226 parameters
wR(F2) = 0.097H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å−3
3886 reflectionsΔρmin = −0.29 e Å−3
Special details top

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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.11052 (4)1.01754 (2)0.126498 (9)0.03627 (12)
O10.0701 (2)1.11144 (12)0.16469 (5)0.0406 (4)
N10.2013 (3)0.92459 (14)0.16125 (6)0.0355 (5)
N20.1609 (3)0.91868 (15)0.08457 (6)0.0394 (5)
N30.0296 (3)1.11223 (18)0.08820 (6)0.0517 (6)
N4−0.0786 (3)1.17598 (18)0.09472 (6)0.0435 (6)
N5−0.1800 (4)1.2398 (2)0.09892 (7)0.0638 (7)
C10.1479 (3)1.01488 (18)0.22235 (8)0.0334 (6)
C20.0797 (3)1.10007 (19)0.20300 (8)0.0355 (6)
C30.0174 (3)1.1829 (2)0.22607 (8)0.0420 (6)
H3−0.02811.23960.21350.050*
C40.0235 (3)1.1799 (2)0.26581 (8)0.0458 (7)
H4−0.01801.23500.28000.055*
C50.0913 (3)1.0955 (2)0.28661 (7)0.0400 (6)
C60.0994 (4)1.0939 (2)0.32823 (8)0.0519 (8)
H60.05961.14950.34240.062*
C70.1640 (4)1.0127 (3)0.34801 (9)0.0575 (8)
H70.16901.01310.37540.069*
C80.2227 (4)0.9288 (2)0.32689 (8)0.0502 (7)
H80.26620.87290.34030.060*
C90.2169 (3)0.9282 (2)0.28642 (8)0.0435 (7)
H90.25620.87160.27280.052*
C100.1528 (3)1.01158 (19)0.26501 (8)0.0363 (6)
C110.2107 (3)0.93247 (18)0.19959 (7)0.0362 (6)
H110.26320.87940.21320.043*
C120.2765 (4)0.83414 (19)0.14273 (7)0.0441 (7)
H12A0.26270.77620.15990.053*
H12B0.40200.84360.13730.053*
C130.1756 (4)0.81910 (19)0.10506 (8)0.0461 (7)
H13A0.23720.77120.08830.055*
H13B0.05810.79270.11070.055*
C140.3328 (4)0.9506 (2)0.06614 (8)0.0490 (7)
H14A0.42440.95050.08620.059*
H14B0.32041.01910.05660.059*
C150.3927 (4)0.8840 (3)0.03216 (8)0.0623 (9)
H15A0.50060.91130.02080.075*
H15B0.41860.81690.04190.075*
C160.2506 (5)0.8780 (3)0.00090 (9)0.0736 (10)
H16A0.28670.8308−0.01940.088*
H16B0.23520.9436−0.01120.088*
C170.0771 (5)0.8439 (2)0.01886 (9)0.0711 (10)
H17A0.08920.77520.02820.085*
H17B−0.01490.8449−0.00120.085*
C180.0223 (4)0.9118 (2)0.05305 (8)0.0517 (7)
H18A−0.00190.97880.04300.062*
H18B−0.08670.88600.06450.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0394 (2)0.02563 (18)0.0438 (2)0.00147 (14)−0.00179 (15)0.00165 (15)
O10.0522 (11)0.0259 (9)0.0437 (10)0.0041 (8)−0.0025 (8)0.0024 (8)
N10.0340 (12)0.0249 (11)0.0475 (13)0.0028 (9)−0.0028 (9)−0.0006 (10)
N20.0427 (13)0.0313 (12)0.0442 (12)0.0014 (10)−0.0093 (10)−0.0003 (10)
N30.0725 (17)0.0371 (13)0.0456 (13)0.0140 (13)0.0023 (12)0.0045 (12)
N40.0570 (16)0.0361 (13)0.0374 (13)−0.0015 (12)−0.0060 (11)0.0044 (11)
N50.0761 (18)0.0562 (17)0.0591 (17)0.0239 (15)−0.0021 (14)0.0058 (14)
C10.0281 (12)0.0263 (12)0.0458 (15)−0.0040 (10)−0.0017 (10)0.0009 (12)
C20.0304 (14)0.0276 (13)0.0483 (16)−0.0045 (11)0.0023 (11)−0.0031 (12)
C30.0359 (15)0.0303 (14)0.0597 (18)0.0005 (12)0.0027 (13)−0.0022 (13)
C40.0400 (16)0.0369 (16)0.0604 (19)−0.0019 (13)0.0088 (13)−0.0112 (14)
C50.0302 (14)0.0440 (16)0.0458 (16)−0.0085 (12)0.0033 (11)−0.0058 (13)
C60.0425 (17)0.058 (2)0.0548 (18)−0.0080 (15)0.0060 (14)−0.0114 (16)
C70.0463 (17)0.080 (2)0.0462 (18)−0.0157 (17)0.0027 (14)−0.0036 (17)
C80.0406 (16)0.0568 (19)0.0531 (18)−0.0119 (14)−0.0061 (13)0.0124 (16)
C90.0387 (15)0.0418 (16)0.0498 (17)−0.0079 (13)−0.0022 (12)0.0032 (14)
C100.0275 (13)0.0358 (14)0.0457 (15)−0.0101 (11)0.0003 (10)−0.0009 (12)
C110.0319 (14)0.0289 (14)0.0479 (16)−0.0030 (11)−0.0033 (11)0.0057 (12)
C120.0549 (17)0.0287 (14)0.0487 (16)0.0092 (13)−0.0058 (13)0.0003 (13)
C130.0609 (18)0.0265 (14)0.0509 (17)0.0031 (13)−0.0034 (14)−0.0037 (13)
C140.0471 (16)0.0543 (18)0.0458 (16)−0.0012 (14)−0.0020 (13)−0.0019 (15)
C150.066 (2)0.072 (2)0.0486 (17)0.0199 (18)0.0024 (15)−0.0048 (17)
C160.099 (3)0.075 (2)0.0468 (18)0.031 (2)−0.0117 (19)−0.0095 (18)
C170.096 (3)0.051 (2)0.066 (2)0.0106 (19)−0.043 (2)−0.0147 (17)
C180.0501 (18)0.0435 (17)0.0613 (18)0.0003 (14)−0.0202 (14)−0.0029 (15)
Geometric parameters (Å, °) top
Ni1—O11.8226 (17)C7—H70.9300
Ni1—N11.838 (2)C8—C91.373 (4)
Ni1—N31.907 (2)C8—H80.9300
Ni1—N21.971 (2)C9—C101.408 (3)
O1—C21.310 (3)C9—H90.9300
N1—C111.306 (3)C11—H110.9300
N1—C121.468 (3)C12—C131.500 (4)
N2—C181.497 (3)C12—H12A0.9700
N2—C131.497 (3)C12—H12B0.9700
N2—C141.499 (3)C13—H13A0.9700
N3—N41.195 (3)C13—H13B0.9700
N4—N51.149 (3)C14—C151.520 (4)
C1—C21.404 (3)C14—H14A0.9700
C1—C111.419 (3)C14—H14B0.9700
C1—C101.448 (4)C15—C161.508 (4)
C2—C31.428 (3)C15—H15A0.9700
C3—C41.349 (3)C15—H15B0.9700
C3—H30.9300C16—C171.511 (5)
C4—C51.419 (4)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C101.410 (3)C17—C181.525 (4)
C5—C61.413 (4)C17—H17A0.9700
C6—C71.359 (4)C17—H17B0.9700
C6—H60.9300C18—H18A0.9700
C7—C81.396 (4)C18—H18B0.9700
O1—Ni1—N193.73 (8)C5—C10—C1119.1 (2)
O1—Ni1—N388.87 (9)N1—C11—C1125.8 (2)
N1—Ni1—N3176.16 (10)N1—C11—H11117.1
O1—Ni1—N2178.12 (8)C1—C11—H11117.1
N1—Ni1—N286.82 (9)N1—C12—C13106.1 (2)
N3—Ni1—N290.49 (9)N1—C12—H12A110.5
C2—O1—Ni1128.09 (16)C13—C12—H12A110.5
C11—N1—C12118.1 (2)N1—C12—H12B110.5
C11—N1—Ni1127.20 (17)C13—C12—H12B110.5
C12—N1—Ni1114.69 (16)H12A—C12—H12B108.7
C18—N2—C13109.2 (2)N2—C13—C12108.4 (2)
C18—N2—C14108.8 (2)N2—C13—H13A110.0
C13—N2—C14112.3 (2)C12—C13—H13A110.0
C18—N2—Ni1114.96 (16)N2—C13—H13B110.0
C13—N2—Ni1105.47 (15)C12—C13—H13B110.0
C14—N2—Ni1106.21 (15)H13A—C13—H13B108.4
N4—N3—Ni1123.93 (19)N2—C14—C15114.1 (2)
N5—N4—N3176.0 (3)N2—C14—H14A108.7
C2—C1—C11119.2 (2)C15—C14—H14A108.7
C2—C1—C10120.0 (2)N2—C14—H14B108.7
C11—C1—C10120.8 (2)C15—C14—H14B108.7
O1—C2—C1125.2 (2)H14A—C14—H14B107.6
O1—C2—C3115.9 (2)C16—C15—C14110.7 (3)
C1—C2—C3118.9 (2)C16—C15—H15A109.5
C4—C3—C2120.9 (3)C14—C15—H15A109.5
C4—C3—H3119.5C16—C15—H15B109.5
C2—C3—H3119.5C14—C15—H15B109.5
C3—C4—C5122.1 (3)H15A—C15—H15B108.1
C3—C4—H4118.9C15—C16—C17110.3 (3)
C5—C4—H4118.9C15—C16—H16A109.6
C10—C5—C6119.5 (3)C17—C16—H16A109.6
C10—C5—C4118.9 (2)C15—C16—H16B109.6
C6—C5—C4121.6 (3)C17—C16—H16B109.6
C7—C6—C5121.4 (3)H16A—C16—H16B108.1
C7—C6—H6119.3C16—C17—C18111.3 (3)
C5—C6—H6119.3C16—C17—H17A109.4
C6—C7—C8119.5 (3)C18—C17—H17A109.4
C6—C7—H7120.3C16—C17—H17B109.4
C8—C7—H7120.3C18—C17—H17B109.4
C9—C8—C7120.5 (3)H17A—C17—H17B108.0
C9—C8—H8119.8N2—C18—C17113.0 (2)
C7—C8—H8119.8N2—C18—H18A109.0
C8—C9—C10121.5 (3)C17—C18—H18A109.0
C8—C9—H9119.3N2—C18—H18B109.0
C10—C9—H9119.3C17—C18—H18B109.0
C9—C10—C5117.7 (2)H18A—C18—H18B107.8
C9—C10—C1123.2 (2)
Acknowledgements top

The authors thank Kaili College for financial support.

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

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Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

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