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In the title compound, [NiCl2(C15H26N2)], the chiral alkaloid (6R,7S,8S,14S)-(-)-L-sparteine acts as a bidentate ligand, with two chloride ligands occupying the remaining coordination sites, producing a slightly distorted tetrahedron. The N-Ni-N plane in the title complex is twisted by 81.31 (11)° from the Cl-Ni-Cl plane. Other distortions of the tetrahedron are discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104004494/ta1437sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104004494/ta1437Isup2.hkl
Contains datablock I

CCDC reference: 237915

Comment top

The majority of four-coordinate NiII complexes prefer to adopt a square-planar structure as a consequence of the d8 configuration. In tetrahedral coordination, the occupation of the unique high-energy antibonding dx2-y2 orbital is unavoidable and so relatively few tetrahedral NiII complexes are known (Cotton et al., 1999). The tetrahedral NiII complexes are mainly of the stoichiometric types NiX42−, NiX2L2 and Ni(L–L)2, where X usually represents a halogen ion, L is a neutral monodentate ligand and L–L is one of several types of bulky bidentate anion (Ban et al., 1973; Koester & Dunn, 1975; Cruse & Gerloch, 1977).

The (-)-sparteine C15H26N2, a naturally occurring tertiary diamine, has attracted research attention; it has been intensively utilized in medicinal chemistry (Cady et al.,1977), in the asymmetric synthesis of chiral compounds (Kretchmer, 1972; Mason & Peacock, 1973; Beak et al., 1996) and in the preparation of a model compound for the type I copper(II) site in metalloproteins (Kim et al., 2001). The structures of several metal(II) sparteine complexes of type [MX2(C15H26N2)] (M = CII, CuII and ZnII; X = Cl, Br and N3) have been reported, and the metal moieties in these compounds are known, without exception, to have a slightly distorted tetrahedral geometry (Kim et al., 2001, 2003; Kuroda & Mason, 1979; Lee et al., 2000; Lee et al., 2002a, 2003a; Lee et al., 2003b; Lopez et al., 1998). This bidentate ligand contains sufficiently bulky substituents on, and adjacent to, the two nitrogen donor atoms to render the planarity of the MX2(L—L) molecule sterically impossible, and generates a distorted tetrahedron around the metal centers.

Synthesis of the title compound, (I), was prompted by our interest in the preparation of a new paramagnetic and tetrahedral NiII compound of the type [NiIIX2(L—L)], and our attempt to compare the stability, coordination geometry and bonding parameters of (I) with analogous CoII, CuII and ZnII (-)-sparteine dichlorides for which the structures are already known (Kuroda & Mason, 1979; Lopez et al., 1998; Lee et al., 2003b).

As expected from previous studies (Choi et al., 1995; Kim et al., 2001, 2003; Kuroda & Mason, 1979; Lee et al., 2000; Lee et al., 2002a, 2003a; Lee et al., 2003b; Lopez et al., 1998), the conformation of the coordinated (-)-sparteine ligand consists of one terminal ring folded down over the metal (endo) and a second terminal ring folded back away from the metal (exo), identical to the conformation of the free ligand (Boschmann et al., 1974; Wrobleski & Long, 1977) or monoprotonated sparteinium salt (Lee et al., 2002b).

In CuCl2(C15H26N2), one consequence of the endo–exo configuration is the slight asymmetry in the Cu—N bond lengths; the endo ring has a shorter Cu—N1 bond length [2.003 (3) Å, compared with 2.021 (3) Å for Cu—N9 (Lopez et al., 1998)]. However, in (I), the two Ni—N bond distances are similar to a more symmetric configuration. The Ni—N bond distances are slightly longer than those in CuCl2(C15H26N2) but are shorter than those in CoCl2(C15H26N2) [2.040 (7) and 2.068 (8) Å] and ZnCl2(C15H26N2) [2.085 (7) and 2.087 (7) Å]. The stability of complexes of the 3 d metal ions with a given ligand almost invariably follows the order Co2+ < Ni2+ < Cu2+ > Zn2+ (Irving & Williams, 1953). A similar trend is observable in this series of metal(II) sparteine compounds if it is assumed that the stability of the complexes is inversely related to the metal(II)–nitrogen bond distances.

The dihedral angle between the N1/Ni/N9 and Cl1/Ni/Cl2 planes in (I) is 81.31 (11) ° and is only about 8.7° less than the perfect tetrahedral angle of 90°. The dihedral angles between the N/M/N and Cl/M/Cl (M = CuII or ZnII) planes in CuCl2(C15H26N2) and ZnCl2(C15H26N2) are reported to be 67.0 and 82.2°, respectively (Lee et al., 2003a; Lopez et al., 1998). The dihedral angle in (I) is very close to that of zinc(II) sparteine dichloride but is much larger than that of copper(II) sparteine dichloride. The ZnII atom has a closed-shell electronic structure of d10, and as a result the molecular structure of ZnCl2(C15H26N2) has to be determined solely by the steric effect. The very similar values in the dihedral angles of the NiII and ZnII compounds suggest that the electronic effect in the molecular structure of (I) is not as important as in the analogous CuII compound, and that the molecular structure is determined by intramolecular steric interactions between the (-)-sparteine ligand and the chloride ions coordinated with NiII. The smaller dihedral angle of 67.0° reported for CuCl2(C15H26N2) is definitely a result of the balance of the electronic effect of the d9 system and the steric effect imposed by a bulky (-)-sparteine ligand (Figgis, 1966).

Another way of looking at the distortion of the tetrahedron is to compare the 'bite angle' and the 'tilt' of the bidentate (-)-sparteine ligand with respect to the Cl/Ni/Cl plane (Lee et al., 2002a, 2003a). The mid-point of the N1···N9 line does not lie on the Cl1/Ni/Cl2 plane but is tilted towards N1 by 0.193 Å (13.5% of half of the N1···N9 distance). Similarly, the mid-point of the Cl1···Cl2 line is tilted toward atom Cl2 by 0.144 Å (7.4% of half of the Cl1···Cl2 distance). The N1—Ni—Cl1 and N9—Ni—Cl2 angles are similar; however, the N1—Ni—Cl2 and N9—Ni—Cl1 angles differ by more than 10°.

In NiII complexes, even slight distortion from the perfect tetrahedron reduces the magnetic moment markedly by splitting the orbital degeneracy (Cotton et al., 1999). The room-temperature magnetic moment of (I), estimated from the relation µeff = 2.828(χM × T)1/2, is 3.3 BM. This value is much smaller than the vaule of around 4.2 BM that is usually exhibited by truly tetrahedral NiII complexes.

Experimental top

Complex (I) was prepared by the direct reaction of nickel(II) chloride with a stoichiometric amount of (-)-l-sparteine in an ethanol-triethylorthoformate (5:1 v/v) solution. The resulting violet precipitate was filtered, washed with cold absolute ethanol and dried in a vacuum. Single crystals were obtained by recrystallization at room temperature in a dichloromethane–triethylorthoformate (5:1 v/v) solution. Analysis calculated for C15H26N2NiCl2: C 49.49, H 7.20, N 7.70%; found: C 49.50, H 7.14, N 7.74%.

Refinement top

H atoms on the sparteine ligand were positioned geometrically and constrained to ride on their attached atoms at distances of 0.97–0.98 Å. The Uiso(H) values were fixed at 1.2Ueq of the parent atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) diagram of (I), showing the atom-numbering scheme and 30% probability ellipsoids. H atoms have been omitted for clarity.
dichloro[(-)-sparteine-N,N']nickel(II) top
Crystal data top
[NiCl2(C15H26N2)]F(000) = 768
Mr = 363.99Dx = 1.484 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 24 reflections
a = 11.1357 (17) Åθ = 11.5–12.6°
b = 11.8679 (14) ŵ = 1.51 mm1
c = 12.3278 (19) ÅT = 293 K
V = 1629.2 (4) Å3Block, dark violet
Z = 40.3 × 0.3 × 0.26 mm
Data collection top
Enraf Nonius CAD4
diffractometer
2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
Non–profiled ω/2θ scansh = 1414
Absorption correction: ψ scan
(North et al., 1968)
k = 015
Tmin = 0.612, Tmax = 0.672l = 016
4063 measured reflections3 standard reflections every 400 reflections
3730 independent reflections intensity decay: 4%
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0655P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3730 reflectionsΔρmax = 0.64 e Å3
181 parametersΔρmin = 0.50 e Å3
0 restraintsAbsolute structure: Flack (1983), 1597 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (3)
Crystal data top
[NiCl2(C15H26N2)]V = 1629.2 (4) Å3
Mr = 363.99Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.1357 (17) ŵ = 1.51 mm1
b = 11.8679 (14) ÅT = 293 K
c = 12.3278 (19) Å0.3 × 0.3 × 0.26 mm
Data collection top
Enraf Nonius CAD4
diffractometer
2855 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.037
Tmin = 0.612, Tmax = 0.6723 standard reflections every 400 reflections
4063 measured reflections intensity decay: 4%
3730 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.130Δρmax = 0.64 e Å3
S = 1.03Δρmin = 0.50 e Å3
3730 reflectionsAbsolute structure: Flack (1983), 1597 Friedel pairs
181 parametersAbsolute structure parameter: 0.00 (3)
0 restraints
Special details top

Experimental. The magnetic susceptibility measurements were made on a powdered sample of (I) with a Quantum Design MPMS7-SQUID susceptometer. The data was corrected for the diamagnetism of the constituent atoms with Pascal's constant.

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
xyzUiso*/Ueq
Ni0.19791 (6)0.26426 (5)0.12988 (5)0.02943 (17)
Cl10.18039 (17)0.43613 (12)0.05722 (11)0.0546 (4)
Cl20.21219 (16)0.11399 (12)0.02154 (11)0.0485 (4)
N10.3053 (4)0.2910 (3)0.2606 (3)0.0284 (8)
C20.4278 (5)0.3240 (5)0.2233 (5)0.0394 (13)
H2A0.47630.34410.28570.047*
H2B0.42170.38990.17700.047*
C30.4886 (5)0.2306 (5)0.1619 (4)0.0423 (13)
H3A0.56830.25490.14020.051*
H3B0.44320.21390.09680.051*
C40.4986 (5)0.1255 (5)0.2303 (5)0.0466 (15)
H4A0.55350.13890.29010.056*
H4B0.53080.06450.18680.056*
C50.3756 (5)0.0919 (5)0.2749 (5)0.0422 (14)
H5A0.32520.06640.21560.051*
H5B0.38520.02980.32520.051*
C60.3145 (5)0.1894 (4)0.3323 (4)0.0342 (11)
H60.36710.21060.39270.041*
C70.1920 (5)0.1625 (4)0.3820 (4)0.0369 (11)
H70.20210.09680.42930.044*
C80.1344 (5)0.3603 (4)0.3768 (5)0.0350 (12)
H80.11150.42520.42130.042*
N90.0584 (3)0.2328 (3)0.2311 (3)0.0259 (8)
C100.0454 (5)0.2062 (5)0.1577 (4)0.0374 (13)
H10A0.02960.13500.12170.045*
H10B0.05010.26380.10200.045*
C110.1655 (5)0.1987 (5)0.2140 (5)0.0438 (14)
H11A0.16440.13730.26590.053*
H11B0.22790.18350.16120.053*
C120.1920 (5)0.3087 (5)0.2721 (4)0.0423 (13)
H12A0.26810.30320.31000.051*
H12B0.19760.36960.21990.051*
C130.0919 (5)0.3329 (5)0.3525 (4)0.0391 (13)
H13A0.09150.27500.40800.047*
H13B0.10710.40470.38760.047*
C140.0313 (5)0.3366 (4)0.2970 (4)0.0304 (11)
H140.02930.39990.24600.037*
C150.2538 (5)0.3868 (5)0.3236 (4)0.0381 (13)
H15A0.24340.45060.27530.046*
H15B0.31070.40870.37930.046*
C160.0913 (5)0.1345 (4)0.2999 (5)0.0345 (12)
H16A0.11760.07320.25370.041*
H16B0.02080.10930.33920.041*
C170.1512 (5)0.2596 (5)0.4519 (4)0.0448 (14)
H17A0.21100.27630.50680.054*
H17B0.07620.24130.48780.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.0364 (3)0.0332 (3)0.0186 (3)0.0020 (3)0.0027 (3)0.0004 (3)
Cl10.0840 (13)0.0449 (8)0.0351 (7)0.0023 (8)0.0051 (8)0.0147 (6)
Cl20.0677 (11)0.0446 (7)0.0332 (6)0.0047 (8)0.0037 (7)0.0119 (6)
N10.030 (2)0.028 (2)0.0268 (19)0.0001 (19)0.0025 (19)0.0004 (15)
C20.037 (3)0.042 (3)0.039 (3)0.010 (2)0.001 (3)0.004 (3)
C30.034 (3)0.050 (3)0.044 (3)0.000 (3)0.004 (2)0.004 (3)
C40.037 (3)0.051 (4)0.052 (4)0.012 (3)0.003 (3)0.007 (3)
C50.040 (3)0.039 (3)0.048 (3)0.010 (3)0.004 (3)0.014 (3)
C60.034 (3)0.041 (3)0.027 (2)0.001 (3)0.000 (2)0.007 (2)
C70.036 (3)0.047 (3)0.028 (2)0.007 (3)0.003 (3)0.014 (2)
C80.039 (3)0.039 (3)0.027 (3)0.003 (2)0.001 (3)0.016 (3)
N90.026 (2)0.029 (2)0.0221 (18)0.0000 (18)0.0013 (15)0.0050 (18)
C100.035 (3)0.041 (3)0.036 (3)0.005 (2)0.006 (2)0.008 (2)
C110.034 (3)0.054 (3)0.043 (3)0.006 (2)0.008 (2)0.007 (3)
C120.032 (3)0.054 (3)0.041 (3)0.006 (3)0.001 (3)0.011 (3)
C130.043 (3)0.049 (3)0.025 (3)0.007 (3)0.009 (2)0.002 (2)
C140.037 (3)0.031 (3)0.024 (2)0.002 (2)0.000 (2)0.002 (2)
C150.041 (3)0.040 (3)0.034 (3)0.001 (2)0.005 (2)0.013 (3)
C160.036 (3)0.029 (3)0.039 (3)0.001 (2)0.006 (2)0.011 (2)
C170.044 (3)0.069 (4)0.021 (2)0.006 (3)0.001 (2)0.003 (3)
Geometric parameters (Å, º) top
Ni—N12.032 (4)C8—C171.524 (8)
Ni—N92.027 (4)C8—C141.538 (7)
Ni—Cl12.2363 (15)C8—H80.9800
Ni—Cl22.2337 (14)N9—C101.502 (6)
N1—C21.492 (7)N9—C141.506 (6)
N1—C61.498 (6)N9—C161.488 (6)
N1—C151.491 (6)C10—C111.510 (8)
C2—C31.503 (7)C10—H10A0.9700
C2—H2A0.9700C10—H10B0.9700
C2—H2B0.9700C11—C121.518 (8)
C3—C41.510 (8)C11—H11A0.9700
C3—H3A0.9700C11—H11B0.9700
C3—H3B0.9700C12—C131.518 (8)
C4—C51.528 (8)C12—H12A0.9700
C4—H4A0.9700C12—H12B0.9700
C4—H4B0.9700C13—C141.534 (7)
C5—C61.517 (7)C13—H13A0.9700
C5—H5A0.9700C13—H13B0.9700
C5—H5B0.9700C14—H140.9800
C6—C71.529 (8)C15—H15A0.9700
C6—H60.9800C15—H15B0.9700
C7—C171.510 (8)C16—H16A0.9700
C7—C161.546 (7)C16—H16B0.9700
C7—H70.9800C17—H17A0.9700
C8—C151.516 (8)C17—H17B0.9700
N1—Ni—N989.51 (16)C16—N9—C10111.6 (4)
N1—Ni—Cl1103.10 (11)C16—N9—C14112.5 (4)
N1—Ni—Cl2123.85 (12)C10—N9—C14110.1 (4)
N9—Ni—Cl1110.35 (12)C16—N9—Ni107.9 (3)
N9—Ni—Cl2105.99 (12)C10—N9—Ni104.9 (3)
Cl1—Ni—Cl2119.67 (6)C14—N9—Ni109.6 (3)
C15—N1—C2108.1 (4)N9—C10—C11114.6 (4)
C15—N1—C6109.4 (4)N9—C10—H10A108.6
C2—N1—C6109.3 (4)C11—C10—H10A108.6
C15—N1—Ni107.8 (3)N9—C10—H10B108.6
C2—N1—Ni109.5 (3)C11—C10—H10B108.6
C6—N1—Ni112.5 (3)H10A—C10—H10B107.6
N1—C2—C3111.9 (4)C10—C11—C12109.8 (5)
N1—C2—H2A109.2C10—C11—H11A109.7
C3—C2—H2A109.2C12—C11—H11A109.7
N1—C2—H2B109.2C10—C11—H11B109.7
C3—C2—H2B109.2C12—C11—H11B109.7
H2A—C2—H2B107.9H11A—C11—H11B108.2
C2—C3—C4111.2 (4)C11—C12—C13109.2 (5)
C2—C3—H3A109.4C11—C12—H12A109.8
C4—C3—H3A109.4C13—C12—H12A109.8
C2—C3—H3B109.4C11—C12—H12B109.8
C4—C3—H3B109.4C13—C12—H12B109.8
H3A—C3—H3B108.0H12A—C12—H12B108.3
C3—C4—C5110.5 (5)C12—C13—C14111.7 (4)
C3—C4—H4A109.6C12—C13—H13A109.3
C5—C4—H4A109.6C14—C13—H13A109.3
C3—C4—H4B109.6C12—C13—H13B109.3
C5—C4—H4B109.6C14—C13—H13B109.3
H4A—C4—H4B108.1H13A—C13—H13B107.9
C6—C5—C4111.8 (5)N9—C14—C13113.4 (4)
C6—C5—H5A109.3N9—C14—C8110.2 (4)
C4—C5—H5A109.3C13—C14—C8112.8 (4)
C6—C5—H5B109.3N9—C14—H14106.7
C4—C5—H5B109.3C13—C14—H14106.7
H5A—C5—H5B107.9C8—C14—H14106.7
N1—C6—C5111.6 (4)N1—C15—C8113.8 (4)
N1—C6—C7110.1 (4)N1—C15—H15A108.8
C5—C6—C7115.3 (4)C8—C15—H15A108.8
N1—C6—H6106.4N1—C15—H15B108.8
C5—C6—H6106.4C8—C15—H15B108.8
C7—C6—H6106.4H15A—C15—H15B107.7
C17—C7—C6109.7 (4)N9—C16—C7112.5 (4)
C17—C7—C16108.6 (4)N9—C16—H16A109.1
C6—C7—C16115.4 (4)C7—C16—H16A109.1
C17—C7—H7107.6N9—C16—H16B109.1
C6—C7—H7107.6C7—C16—H16B109.1
C16—C7—H7107.6H16A—C16—H16B107.8
C15—C8—C17108.6 (4)C7—C17—C8106.8 (4)
C15—C8—C14114.6 (4)C7—C17—H17A110.4
C17—C8—C14109.7 (4)C8—C17—H17A110.4
C15—C8—H8107.9C7—C17—H17B110.4
C17—C8—H8107.9C8—C17—H17B110.4
C14—C8—H8107.9H17A—C17—H17B108.6
N9—Ni—N1—C1560.3 (3)Cl2—Ni—N9—C14172.2 (3)
Cl2—Ni—N1—C15169.3 (3)Cl1—Ni—N9—C1441.3 (3)
Cl1—Ni—N1—C1550.5 (3)C16—N9—C10—C1173.2 (6)
N9—Ni—N1—C2177.7 (3)C14—N9—C10—C1152.5 (6)
Cl2—Ni—N1—C273.2 (3)Ni—N9—C10—C11170.2 (4)
Cl1—Ni—N1—C266.9 (3)N9—C10—C11—C1257.7 (6)
N9—Ni—N1—C660.5 (3)C10—C11—C12—C1357.9 (6)
Cl2—Ni—N1—C648.6 (4)C11—C12—C13—C1456.7 (6)
Cl1—Ni—N1—C6171.3 (3)C16—N9—C14—C1375.8 (5)
C15—N1—C2—C3178.1 (4)C10—N9—C14—C1349.4 (5)
C6—N1—C2—C359.0 (5)Ni—N9—C14—C13164.2 (3)
Ni—N1—C2—C364.7 (5)C16—N9—C14—C851.7 (5)
N1—C2—C3—C458.1 (6)C10—N9—C14—C8176.9 (4)
C2—C3—C4—C553.6 (7)Ni—N9—C14—C868.3 (4)
C3—C4—C5—C652.3 (7)C12—C13—C14—N953.5 (6)
C15—N1—C6—C5175.4 (4)C12—C13—C14—C8179.6 (4)
C2—N1—C6—C557.2 (6)C15—C8—C14—N963.3 (5)
Ni—N1—C6—C564.8 (5)C17—C8—C14—N959.0 (5)
C15—N1—C6—C755.1 (5)C15—C8—C14—C13168.8 (4)
C2—N1—C6—C7173.4 (4)C17—C8—C14—C1368.8 (5)
Ni—N1—C6—C764.7 (4)C2—N1—C15—C8173.8 (4)
C4—C5—C6—N154.9 (6)C6—N1—C15—C854.8 (6)
C4—C5—C6—C7178.5 (4)Ni—N1—C15—C867.8 (5)
N1—C6—C7—C1762.1 (5)C17—C8—C15—N158.2 (6)
C5—C6—C7—C17170.5 (4)C14—C8—C15—N164.8 (6)
N1—C6—C7—C1661.1 (6)C10—N9—C16—C7175.9 (4)
C5—C6—C7—C1666.3 (6)C14—N9—C16—C751.6 (5)
N1—Ni—N9—C1660.3 (3)Ni—N9—C16—C769.4 (4)
Cl2—Ni—N9—C1665.0 (3)C17—C7—C16—N957.6 (5)
Cl1—Ni—N9—C16164.1 (3)C6—C7—C16—N966.2 (6)
N1—Ni—N9—C10179.4 (3)C6—C7—C17—C864.0 (5)
Cl2—Ni—N9—C1054.1 (3)C16—C7—C17—C863.1 (6)
Cl1—Ni—N9—C1076.8 (3)C15—C8—C17—C760.7 (6)
N1—Ni—N9—C1462.5 (3)C14—C8—C17—C765.2 (6)

Experimental details

Crystal data
Chemical formula[NiCl2(C15H26N2)]
Mr363.99
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)11.1357 (17), 11.8679 (14), 12.3278 (19)
V3)1629.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.51
Crystal size (mm)0.3 × 0.3 × 0.26
Data collection
DiffractometerEnraf Nonius CAD4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.612, 0.672
No. of measured, independent and
observed [I > 2σ(I)] reflections
4063, 3730, 2855
Rint0.037
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.130, 1.03
No. of reflections3730
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.50
Absolute structureFlack (1983), 1597 Friedel pairs
Absolute structure parameter0.00 (3)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Ni—N12.032 (4)N1—C61.498 (6)
Ni—N92.027 (4)N1—C151.491 (6)
Ni—Cl12.2363 (15)N9—C101.502 (6)
Ni—Cl22.2337 (14)N9—C141.506 (6)
N1—C21.492 (7)N9—C161.488 (6)
N1—Ni—N989.51 (16)N9—Ni—Cl1110.35 (12)
N1—Ni—Cl1103.10 (11)N9—Ni—Cl2105.99 (12)
N1—Ni—Cl2123.85 (12)Cl1—Ni—Cl2119.67 (6)
 

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