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Acta Cryst. (2009). E65, o1313    [ doi:10.1107/S1600536809017504 ]

Cyclohexanaminium trichloroacetate

D. Shahwar, M. N. Tahir, N. Ahmad, M. A. Khan and A. Saeed

Abstract top

In the crystal of the title compound, C6H14N+·C2Cl3O2-, centrosymmetric assemblies of two cyclohexanaminium cations and two trichloroacetate ions are linked by N-H...O hydrogen bonds, thereby forming R44(12) ring motifs. Further N-H...O interactions link the tetramers into chains propagating along the a axis.

Comment top

In continuation of synthesizing various organic ammonium salts (Shahwar et al., 2009), the title compound (I), (Fig. 1) is being reported. The crystal structures of (II) Cyclohexylammonium dichloroacetate (Wang et al., 2005) and (III) Cyclohexylamine cyclohexylammonium chloride (Jones & Ahrens, 1998) have been reported.

In (I), the bond distance and bond angles are within normal ranges (Allen et al., 1987). In the title compound, two cyclohexanaminium ions and two trichloroacetate ions are interlinked through intermolecular H-bonding of N—H···O type (Table 1) forming ring motifs R44(12) (Bernstein et al., 1995) (Fig. 2). The ring motifs are further connected through the same along the a axis resulting in one-dimensional polymeric chains. The cyclohexanaminium ions are in chair confirmations with N-atoms at a distance of 0.628 (9)Å from the central plane.

Related literature top

For related structures, see: Shahwar et al. (2009); Wang et al. (2005); Jones & Ahrens (1998). For reference structural data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A solution of trichloroacetic acid (1.635 g, 0.01 mol) in 20 ml of dichloromethane was prepared. To this solution cyclohexyl amine (1.14 ml, 0.01 mol) was added dropwise and stirred for 30 min. The precipitate were filtered out and recrystallized in hot chloroform to yield colourless rods of (I).

Refinement top

The coordinates of H-atoms attached to N1 and C1 were refined. The other H atoms were positioned geometrically (C—H = 0.97 Å) and refined as riding. The constraint Uiso(H) = 1.2Ueq(carrier) was applied for all H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small spheres of arbitrary radius.
[Figure 2] Fig. 2. The partial packing in (I) showing intermolecular H-bonding between NH3 and trichloroacetate ions and the resulting ring motif.
Cyclohexanaminium trichloroacetate top
Crystal data top
C6H14N+·C2Cl3O2–F000 = 544
Mr = 262.55Dx = 1.422 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2910 reflections
a = 6.7217 (4) Åθ = 2.6–27.9º
b = 21.2482 (15) ŵ = 0.72 mm−1
c = 10.6908 (6) ÅT = 296 K
β = 126.590 (3)ºRod, colorless
V = 1225.98 (14) Å30.25 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2910 independent reflections
Radiation source: fine-focus sealed tube1710 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.038
Detector resolution: 7.50 pixels mm-1θmax = 27.9º
T = 296 Kθmin = 2.6º
ω scansh = −8→8
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −27→26
Tmin = 0.853, Tmax = 0.919l = −12→14
13379 measured reflections
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)] = 0.066H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.215  w = 1/[σ2(Fo2) + (0.1089P)2 + 0.5776P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2910 reflectionsΔρmax = 0.73 e Å−3
139 parametersΔρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C6H14N+·C2Cl3O2–V = 1225.98 (14) Å3
Mr = 262.55Z = 4
Monoclinic, P21/cMo Kα
a = 6.7217 (4) ŵ = 0.72 mm−1
b = 21.2482 (15) ÅT = 296 K
c = 10.6908 (6) Å0.25 × 0.18 × 0.12 mm
β = 126.590 (3)º
Data collection top
Bruker Kappa APEXII CCD
diffractometer		2910 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1710 reflections with I > 2σ(I)
Tmin = 0.853, Tmax = 0.919Rint = 0.038
13379 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066139 parameters
wR(F2) = 0.215H atoms treated by a mixture of
independent and constrained refinement
S = 1.05Δρmax = 0.73 e Å−3
2910 reflectionsΔρmin = −0.37 e Å−3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N10.2904 (5)0.05714 (15)0.0547 (4)0.0480 (10)
C10.4574 (6)0.08854 (16)0.2093 (4)0.0463 (10)
C20.7215 (6)0.06696 (19)0.2878 (5)0.0568 (11)
C30.8922 (7)0.0967 (2)0.4465 (5)0.0731 (15)
C40.8100 (8)0.0827 (3)0.5472 (6)0.0816 (18)
C50.5457 (8)0.1032 (2)0.4704 (5)0.0764 (17)
C60.3726 (7)0.0733 (2)0.3100 (5)0.0626 (15)
Cl10.9294 (2)0.30601 (6)0.38465 (15)0.0791 (4)
Cl20.7598 (3)0.28803 (6)0.57059 (16)0.1029 (6)
Cl30.4167 (2)0.28226 (6)0.23280 (17)0.0950 (5)
O10.7893 (5)0.42783 (12)0.4227 (4)0.0711 (9)
O20.4297 (5)0.40429 (14)0.3696 (3)0.0680 (10)
C70.6272 (5)0.39152 (15)0.3948 (3)0.0406 (9)
C80.6778 (7)0.32022 (15)0.3937 (4)0.0488 (10)
H10.432 (7)0.1331 (19)0.186 (4)0.0553*
H1A0.141 (8)0.0678 (19)0.011 (5)0.0575*
H1B0.333 (7)0.0632 (19)−0.002 (5)0.0575*
H1C0.285 (7)0.010 (2)0.071 (4)0.0575*
H2A0.729890.021510.298330.0680*
H2B0.774400.078410.224010.0680*
H3A1.058990.080850.496820.0877*
H3B0.895240.141880.434990.0877*
H4A0.918130.104330.646070.0973*
H4B0.824130.037870.567950.0973*
H5A0.534870.148650.460400.0919*
H5B0.495160.090950.535050.0919*
H6A0.205680.089030.259910.0753*
H6B0.370230.028080.320800.0753*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0401 (14)0.0439 (17)0.0601 (19)0.0011 (12)0.0300 (14)0.0040 (13)
C10.0436 (16)0.0341 (17)0.057 (2)0.0007 (13)0.0278 (16)0.0035 (14)
C20.0426 (17)0.063 (2)0.066 (2)0.0015 (16)0.0331 (17)0.0043 (18)
C30.0463 (19)0.084 (3)0.072 (3)−0.0074 (19)0.026 (2)−0.002 (2)
C40.066 (2)0.093 (4)0.064 (3)−0.002 (2)0.027 (2)−0.007 (2)
C50.079 (3)0.088 (3)0.068 (3)0.003 (2)0.047 (2)−0.010 (2)
C60.0508 (19)0.072 (3)0.074 (3)−0.0019 (18)0.042 (2)−0.001 (2)
Cl10.0779 (7)0.0700 (7)0.0894 (8)0.0142 (5)0.0499 (7)−0.0143 (6)
Cl20.1635 (14)0.0733 (8)0.0817 (9)0.0174 (8)0.0784 (10)0.0311 (6)
Cl30.0748 (7)0.0673 (8)0.0937 (9)−0.0196 (5)0.0236 (7)−0.0294 (6)
O10.0498 (14)0.0401 (14)0.111 (2)−0.0005 (11)0.0413 (15)0.0006 (14)
O20.0564 (15)0.0762 (19)0.0787 (19)0.0110 (13)0.0442 (15)0.0000 (14)
C70.0409 (16)0.0400 (17)0.0342 (15)0.0016 (13)0.0187 (13)0.0004 (12)
C80.0579 (19)0.0354 (17)0.0418 (17)−0.0009 (14)0.0236 (16)0.0005 (13)
Geometric parameters (Å, °) top
Cl1—C81.776 (6)C5—C61.523 (6)
Cl2—C81.762 (4)C1—H10.97 (4)
Cl3—C81.758 (4)C2—H2B0.9700
O1—C71.218 (5)C2—H2A0.9700
O2—C71.217 (5)C3—H3A0.9700
N1—C11.492 (5)C3—H3B0.9700
N1—H1A0.85 (6)C4—H4A0.9700
N1—H1C1.02 (4)C4—H4B0.9700
N1—H1B0.82 (5)C5—H5B0.9700
C1—C61.523 (7)C5—H5A0.9700
C1—C21.513 (7)C6—H6B0.9700
C2—C31.508 (6)C6—H6A0.9700
C3—C41.504 (8)C7—C81.554 (5)
C4—C51.510 (9)
C1—N1—H1C109 (2)H3A—C3—H3B108.00
C1—N1—H1A111 (3)C3—C4—H4A109.00
C1—N1—H1B113 (3)C3—C4—H4B109.00
H1B—N1—H1C110 (4)C5—C4—H4A109.00
H1A—N1—H1B112 (5)C5—C4—H4B109.00
H1A—N1—H1C102 (4)H4A—C4—H4B108.00
N1—C1—C2109.8 (3)C4—C5—H5A110.00
N1—C1—C6109.7 (4)C4—C5—H5B109.00
C2—C1—C6110.7 (3)C6—C5—H5A110.00
C1—C2—C3110.6 (4)C6—C5—H5B109.00
C2—C3—C4111.4 (4)H5A—C5—H5B108.00
C3—C4—C5111.6 (4)C1—C6—H6A109.00
C4—C5—C6110.7 (4)C1—C6—H6B110.00
C1—C6—C5110.5 (4)C5—C6—H6A109.00
N1—C1—H1105 (2)C5—C6—H6B110.00
C2—C1—H1114 (3)H6A—C6—H6B108.00
C6—C1—H1108 (3)O1—C7—O2127.7 (3)
C1—C2—H2A110.00O1—C7—C8116.8 (4)
C1—C2—H2B110.00O2—C7—C8115.5 (3)
C3—C2—H2A110.00Cl1—C8—Cl2107.1 (2)
C3—C2—H2B110.00Cl1—C8—Cl3107.2 (2)
H2A—C2—H2B108.00Cl1—C8—C7112.7 (3)
C2—C3—H3A109.00Cl2—C8—Cl3111.3 (2)
C2—C3—H3B109.00Cl2—C8—C7107.5 (2)
C4—C3—H3A109.00Cl3—C8—C7111.1 (3)
C4—C3—H3B109.00
N1—C1—C2—C3−178.3 (3)C4—C5—C6—C1−55.8 (5)
C6—C1—C2—C3−57.1 (4)O1—C7—C8—Cl1−15.1 (4)
N1—C1—C6—C5178.2 (3)O1—C7—C8—Cl2102.6 (4)
C2—C1—C6—C556.9 (4)O1—C7—C8—Cl3−135.5 (3)
C1—C2—C3—C456.5 (5)O2—C7—C8—Cl1165.9 (2)
C2—C3—C4—C5−55.9 (6)O2—C7—C8—Cl2−76.4 (3)
C3—C4—C5—C655.4 (6)O2—C7—C8—Cl345.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.85 (6)1.96 (6)2.788 (6)167 (4)
N1—H1B···O2ii0.82 (5)1.96 (5)2.770 (5)168 (4)
N1—H1C···O1iii1.02 (4)1.83 (4)2.837 (4)169 (4)
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.85 (6)1.96 (6)2.788 (6)167 (4)
N1—H1B···O2ii0.82 (5)1.96 (5)2.770 (5)168 (4)
N1—H1C···O1iii1.02 (4)1.83 (4)2.837 (4)169 (4)
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2.
Acknowledgements top

NA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042–120599-PS2–156).

references
References top

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