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Acta Cryst. (2008). E64, m415    [ doi:10.1107/S160053680800189X ]

Bis(1-adamantylammonium) tetrachloridocobaltate(II)

H.-M. Guo, H.-Q. Li, G.-L. Zhao and S. W. Ng

Abstract top

The CoII atom in the title salt, (C10H18N)2[CoCl4], exists in a tetrahedral coordination geometry. The asymmetric unit has two cations that lie on different special positions of site symmetry m; the anion lies on another special position of site symmetry m.

Related literature top

Some amines do not form adducts with cobalt(II) chloride; in the reactions, the amines themselves are protonated. For 1,3-propanediammonium tetrachloridocobaltate, see Guo et al. (1992); for tricyclohexylammonium chloride tetrachlorocobaltate, see Geiser et al. (1984); for 4,4'-bipyridinium tetrachloridocobaltate, see Barbour et al. (1996) and Gillon et al. (2000);or bis(4-dimethylamino)pyridinium tetrachloridocobaltate, see Haddad et al. (2003).

Experimental top

1-Aminoadamantane (6.05 g, 40 mmol) and salicylaldehyde (5.01 g, 41 mmol) were heated in ethanol (50 ml) for 1 h. The N-salicylidene-1-aminoadamantane that separated was collected in 70% yield, m.p. 366 K. Cobalt dichloride hexahydrate (1 mmol) dissolved in ethanol (10 ml) was reacted with the Schiff base (2 mmol) dissolved in alcohol (5 ml) to give a blue solution. Blue crystals separated from the solution after three weeks.

Refinement top

H atoms were generated geometrically (C–H 0.97 to 0.98 Å, N–H 0.89 |%A) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 or 1.5Ueq of the parent atom.

Computing details top

Data collection: APEX2 (not SMART) (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 2[C10H18N] [CoCl4]; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. [Symmery code (i) x, –y, z.]
Bis(1-adamantylammonium) tetrachloridocobaltate(II) top
Crystal data top
(C10H18N)2[CoCl4]F000 = 1060
Mr = 505.24Dx = 1.407 Mg m−3
Monoclinic, C2/mMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2yCell parameters from 3080 reflections
a = 30.6005 (6) Åθ = 2.6–22.3º
b = 7.3046 (1) ŵ = 1.18 mm−1
c = 11.0009 (2) ÅT = 295 (2) K
β = 104.087 (1)ºBlock, blue
V = 2385.02 (7) Å30.40 × 0.22 × 0.13 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		2946 independent reflections
Radiation source: fine-focus sealed tube2115 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 295(2) Kθmax = 27.5º
φ and ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −28→39
Tmin = 0.709, Tmax = 0.862k = −9→7
11019 measured reflectionsl = −14→14
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.0368P)2 + 2.5214P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2946 reflectionsΔρmax = 0.52 e Å−3
142 parametersΔρmin = −0.49 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C10H18N)2[CoCl4]V = 2385.02 (7) Å3
Mr = 505.24Z = 4
Monoclinic, C2/mMo Kα
a = 30.6005 (6) ŵ = 1.18 mm−1
b = 7.3046 (1) ÅT = 295 (2) K
c = 11.0009 (2) Å0.40 × 0.22 × 0.13 mm
β = 104.087 (1)º
Data collection top
Bruker APEXII area-detector
diffractometer		2946 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2115 reflections with I > 2σ(I)
Tmin = 0.709, Tmax = 0.862Rint = 0.027
11019 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041142 parameters
wR(F2) = 0.100H-atom parameters constrained
S = 1.05Δρmax = 0.52 e Å−3
2946 reflectionsΔρmin = −0.49 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 > 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*/UeqOcc. (<1)
N10.18030 (9)0.50000.3577 (3)0.0615 (9)
H1A0.19210.40060.33150.092*0.50
H1B0.18630.49990.44100.092*
H1C0.19210.59950.33160.092*0.50
C10.13007 (10)0.50000.3050 (3)0.0452 (8)
C20.11951 (12)0.50000.1618 (3)0.0713 (13)
H2A0.13240.39230.13240.086*0.50
H2B0.13240.60770.13240.086*0.50
C30.06830 (12)0.50000.1108 (3)0.0668 (12)
H30.06110.50000.01900.080*
C40.04858 (9)0.3300 (5)0.1559 (2)0.0737 (9)
H4A0.06130.22140.12710.088*
H4B0.01620.32770.12210.088*
C50.05938 (9)0.3314 (4)0.2990 (2)0.0650 (8)
H50.04650.22220.32860.078*
C60.11079 (8)0.3304 (4)0.3507 (2)0.0568 (7)
H6A0.11810.32890.44150.068*
H6B0.12360.22190.32200.068*
C70.03975 (12)0.50000.3436 (3)0.0691 (12)
H7A0.04630.50000.43440.083*
H7B0.00730.50000.31160.083*
N20.30310 (10)0.50000.1192 (3)0.0888 (13)
H2C0.29040.59890.14310.133*0.50
H2D0.29050.40000.14190.133*0.50
H2E0.29910.50110.03630.133*
C80.35290 (10)0.50000.1809 (3)0.0483 (8)
C90.35959 (12)0.50000.3224 (3)0.0530 (9)
H9A0.34570.60770.34840.064*0.50
H9B0.34570.39230.34840.064*0.50
C100.40942 (14)0.50000.3820 (3)0.0678 (11)
H100.41420.50000.47340.081*
C110.43062 (10)0.3295 (5)0.3422 (3)0.0803 (10)
H11A0.41670.22120.36750.096*
H11B0.46250.32660.38260.096*
C120.42392 (9)0.3305 (4)0.1996 (2)0.0650 (7)
H12A0.43770.22080.17380.078*
C130.37368 (9)0.3305 (4)0.1389 (2)0.0608 (7)
H13A0.36870.33040.04830.073*
H13B0.35980.22160.16340.073*
C140.44527 (13)0.50000.1588 (4)0.0678 (11)
H14A0.47740.50000.19630.081*
H14B0.44080.50000.06840.081*
Co10.244385 (15)0.00000.28152 (4)0.04942 (16)
Cl10.22131 (2)0.24581 (10)0.15542 (7)0.0678 (2)
Cl20.21345 (4)0.00000.44545 (11)0.0907 (4)
Cl30.32036 (3)0.00000.34080 (8)0.0561 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0332 (15)0.098 (3)0.0501 (16)0.0000.0051 (12)0.000
C10.0284 (15)0.067 (2)0.0389 (15)0.0000.0054 (12)0.000
C20.0412 (19)0.132 (4)0.0404 (17)0.0000.0093 (15)0.000
C30.044 (2)0.120 (4)0.0323 (16)0.0000.0007 (14)0.000
C40.0519 (15)0.091 (2)0.0671 (16)−0.0051 (16)−0.0075 (12)−0.0215 (16)
C50.0502 (15)0.070 (2)0.0668 (15)−0.0193 (14)−0.0016 (12)0.0114 (14)
C60.0507 (14)0.0539 (17)0.0582 (14)0.0007 (12)−0.0012 (11)0.0010 (12)
C70.0373 (19)0.120 (4)0.0495 (19)0.0000.0107 (15)0.000
N20.0418 (18)0.133 (4)0.092 (3)0.0000.0173 (17)0.000
C80.0323 (16)0.061 (2)0.0527 (18)0.0000.0119 (14)0.000
C90.070 (2)0.046 (2)0.0535 (18)0.0000.0352 (17)0.000
C100.074 (3)0.091 (3)0.0362 (17)0.0000.0097 (17)0.000
C110.0753 (19)0.097 (3)0.0668 (17)0.0301 (19)0.0144 (14)0.0262 (17)
C120.0609 (16)0.067 (2)0.0719 (16)0.0209 (15)0.0250 (13)−0.0030 (14)
C130.0659 (16)0.0614 (19)0.0603 (14)−0.0134 (14)0.0253 (12)−0.0185 (13)
C140.047 (2)0.093 (3)0.068 (2)0.0000.0234 (18)0.000
Co10.0436 (3)0.0467 (3)0.0547 (3)0.0000.0057 (2)0.000
Cl10.0664 (4)0.0531 (4)0.0775 (4)0.0119 (3)0.0051 (3)0.0092 (3)
Cl20.0614 (6)0.1401 (12)0.0780 (7)0.0000.0311 (5)0.000
Cl30.0433 (5)0.0660 (6)0.0573 (5)0.0000.0090 (4)0.000
Geometric parameters (Å, °) top
N1—C11.505 (4)N2—H2D0.8900
N1—H1A0.8900N2—H2E0.8900
N1—H1B0.8900C8—C131.515 (3)
N1—H1C0.8900C8—C13i1.515 (3)
C1—C6i1.509 (3)C8—C91.520 (4)
C1—C61.509 (3)C9—C101.506 (5)
C1—C21.530 (4)C9—H9A0.9700
C2—C31.530 (5)C9—H9B0.9700
C2—H2A0.9700C10—C111.517 (4)
C2—H2B0.9700C10—C11i1.517 (4)
C3—C4i1.516 (4)C10—H100.9800
C3—C41.516 (4)C11—C121.531 (4)
C3—H30.9800C11—H11A0.9700
C4—C51.528 (4)C11—H11B0.9700
C4—H4A0.9700C12—C141.518 (4)
C4—H4B0.9700C12—C131.520 (4)
C5—C71.504 (4)C12—H12A0.9800
C5—C61.537 (3)C13—H13A0.9700
C5—H50.9800C13—H13B0.9700
C6—H6A0.9700C14—C12i1.518 (4)
C6—H6B0.9700C14—H14A0.9700
C7—C5i1.504 (4)C14—H14B0.9700
C7—H7A0.9700Co1—Cl22.2313 (11)
C7—H7B0.9700Co1—Cl32.2567 (9)
N2—C81.510 (4)Co1—Cl12.2738 (7)
N2—H2C0.8900Co1—Cl1ii2.2738 (7)
C1—N1—H1A109.5C8—N2—H2E109.5
C1—N1—H1B109.5H2C—N2—H2E109.5
H1A—N1—H1B109.5H2D—N2—H2E109.5
C1—N1—H1C109.5N2—C8—C13108.41 (19)
H1A—N1—H1C109.5N2—C8—C13i108.41 (19)
H1B—N1—H1C109.5C13—C8—C13i109.6 (3)
N1—C1—C6i108.50 (17)N2—C8—C9109.3 (3)
N1—C1—C6108.50 (17)C13—C8—C9110.53 (19)
C6i—C1—C6110.3 (3)C13i—C8—C9110.53 (19)
N1—C1—C2109.7 (2)C10—C9—C8108.4 (3)
C6i—C1—C2109.94 (17)C10—C9—H9A110.0
C6—C1—C2109.94 (17)C8—C9—H9A110.0
C1—C2—C3108.5 (3)C10—C9—H9B110.0
C1—C2—H2A110.0C8—C9—H9B110.0
C3—C2—H2A110.0H9A—C9—H9B108.4
C1—C2—H2B110.0C9—C10—C11109.4 (2)
C3—C2—H2B110.0C9—C10—C11i109.4 (2)
H2A—C2—H2B108.4C11—C10—C11i110.3 (4)
C4i—C3—C4110.0 (3)C9—C10—H10109.2
C4i—C3—C2109.49 (19)C11—C10—H10109.2
C4—C3—C2109.49 (19)C11i—C10—H10109.2
C4i—C3—H3109.3C10—C11—C12109.4 (2)
C4—C3—H3109.3C10—C11—H11A109.8
C2—C3—H3109.3C12—C11—H11A109.8
C3—C4—C5109.2 (2)C10—C11—H11B109.8
C3—C4—H4A109.8C12—C11—H11B109.8
C5—C4—H4A109.8H11A—C11—H11B108.2
C3—C4—H4B109.8C14—C12—C13109.4 (3)
C5—C4—H4B109.8C14—C12—C11110.3 (3)
H4A—C4—H4B108.3C13—C12—C11108.6 (2)
C7—C5—C4109.8 (3)C14—C12—H12A109.5
C7—C5—C6109.7 (2)C13—C12—H12A109.5
C4—C5—C6109.0 (2)C11—C12—H12A109.5
C7—C5—H5109.4C8—C13—C12108.7 (2)
C4—C5—H5109.4C8—C13—H13A109.9
C6—C5—H5109.4C12—C13—H13A109.9
C1—C6—C5108.7 (2)C8—C13—H13B109.9
C1—C6—H6A109.9C12—C13—H13B109.9
C5—C6—H6A109.9H13A—C13—H13B108.3
C1—C6—H6B109.9C12i—C14—C12109.3 (3)
C5—C6—H6B109.9C12i—C14—H14A109.8
H6A—C6—H6B108.3C12—C14—H14A109.8
C5—C7—C5i109.9 (3)C12i—C14—H14B109.8
C5—C7—H7A109.7C12—C14—H14B109.8
C5i—C7—H7A109.7H14A—C14—H14B108.3
C5—C7—H7B109.7Cl2—Co1—Cl3112.11 (4)
C5i—C7—H7B109.7Cl2—Co1—Cl1111.30 (3)
H7A—C7—H7B108.2Cl3—Co1—Cl1108.75 (3)
C8—N2—H2C109.5Cl2—Co1—Cl1ii111.30 (3)
C8—N2—H2D109.5Cl3—Co1—Cl1ii108.74 (3)
H2C—N2—H2D109.5Cl1—Co1—Cl1ii104.31 (4)
Symmetry codes: (i) x, −y+1, z; (ii) x, −y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2E···Cl1iii0.892.723.437 (3)139
N2—H2E···Cl1iii0.892.723.437 (3)139
N2—H2D···Cl10.892.433.218 (3)147
N2—H2C···Cl1i0.892.433.218 (3)148
N1—H1C···Cl1i0.892.583.366 (2)147
N1—H1B···Cl3iv0.892.463.322 (3)164
N1—H1A···Cl10.892.583.366 (2)147
Symmetry codes: (iii) −x+1/2, y+1/2, −z; (i) x, −y+1, z; (iv) −x+1/2, −y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2E···Cl1i0.892.723.437 (3)139
N2—H2E···Cl1i0.892.723.437 (3)139
N2—H2D···Cl10.892.433.218 (3)147
N2—H2C···Cl1ii0.892.433.218 (3)148
N1—H1C···Cl1ii0.892.583.366 (2)147
N1—H1B···Cl3iii0.892.463.322 (3)164
N1—H1A···Cl10.892.583.366 (2)147
Symmetry codes: (i) −x+1/2, y+1/2, −z; (ii) x, −y+1, z; (iii) −x+1/2, −y+1/2, −z+1.
Acknowledgements top

The authors thank the Foundation of Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces and the University of Malaya for supporting this study.

references
References top

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