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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1624.
Published online 2008 July 31. doi:  10.1107/S1600536808023155
PMCID: PMC2962233

Dicyclo­hexyl­ammonium bromide

Abstract

In the title compound, C12H24N+·Br, both cyclo­hexane rings adopt the usual chair conformation. The cation and anion are linked by N—H(...)Br hydrogen bonds into a linear chain running along the c axis.

Related literature

For the crystal structure of dicyclo­hexyl­ammonium chloride, which belongs to the space group P21/c, see: Ng (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1624-scheme1.jpg

Experimental

Crystal data

  • C12H24N+·Br
  • M r = 262.23
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1624-efi1.jpg
  • a = 24.1258 (4) Å
  • b = 39.3926 (7) Å
  • c = 5.4878 (1) Å
  • V = 5215.49 (16) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 3.12 mm−1
  • T = 100 (2) K
  • 0.40 × 0.02 × 0.02 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.368, T max = 0.940
  • 15058 measured reflections
  • 2961 independent reflections
  • 2483 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.139
  • S = 0.98
  • 2961 reflections
  • 127 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.56 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1311 Friedel pairs
  • Flack parameter: 0.01 (2)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023155/ci2641sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023155/ci2641Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Malaya for funding this study (grant Nos. SF022/2007A and FS339/2008A) and also for the purchase of the diffractometer.

supplementary crystallographic information

Comment

In the title compound (Fig.1) both cyclohexane rings adopt the usual chair conformation. In the crystal structure, the cation and anion are linked by N—H···Br hydrogen bonds (Table 1) into a linear chain running along the c axis.

Experimental

This compound was obtained as a side product from the reaction between dicyclohexylammonium bis(chlorodifluroacetato)cyclopentyldiphenystannate (0.5 g, 0.6 mmol) and 4-dimethylaminopyridine hydrobromide perbromide (0.23 g, 0.6 mmol) in a mixture of chloroform and ethanol. Crystals were obtained upon evaporation of the solvent.

Refinement

H atoms were placed in calculated positions (N—H = 0.88 Å and C—H = 0.99–1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of [(C6H11)2NH2]+.Br- at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C12H24N+·BrF000 = 2208
Mr = 262.23Dx = 1.336 Mg m3
Orthorhombic, Fdd2Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 3733 reflections
a = 24.1258 (4) Åθ = 2.7–23.5º
b = 39.3926 (7) ŵ = 3.12 mm1
c = 5.4878 (1) ÅT = 100 (2) K
V = 5215.49 (16) Å3Prism, colourless
Z = 160.40 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEXII diffractometer2961 independent reflections
Radiation source: fine-focus sealed tube2483 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 100(2) Kθmax = 27.5º
ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −31→31
Tmin = 0.368, Tmax = 0.940k = −50→50
15058 measured reflectionsl = −7→6

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035  w = 1/[σ2(Fo2) + (0.1P)2 + 1P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max = 0.001
S = 0.98Δρmax = 0.67 e Å3
2961 reflectionsΔρmin = −0.56 e Å3
127 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), with 1311 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.057495 (18)0.153140 (12)0.50000 (6)0.03906 (17)
N1−0.01800 (15)0.14541 (8)1.0006 (10)0.0288 (7)
H110.00300.14791.13050.035*
H120.00360.14750.87240.035*
C1−0.05883 (19)0.17402 (9)0.9961 (13)0.0304 (8)
H1−0.08540.17050.85840.037*
C2−0.0271 (3)0.20707 (12)0.9555 (13)0.0493 (16)
H2A−0.00680.20590.79880.059*
H2B0.00040.21021.08750.059*
C3−0.0668 (4)0.23723 (14)0.9517 (13)0.060 (2)
H3A−0.04540.25850.93400.072*
H3B−0.09190.23520.80980.072*
C4−0.1006 (3)0.23867 (14)1.1826 (12)0.0534 (17)
H4A−0.07580.24381.32160.064*
H4B−0.12800.25731.16970.064*
C5−0.1307 (2)0.20596 (13)1.2315 (17)0.0496 (14)
H5A−0.15920.20241.10440.060*
H5B−0.14980.20751.39090.060*
C6−0.0908 (2)0.17545 (11)1.2338 (15)0.0428 (12)
H6A−0.06460.17761.37180.051*
H6B−0.11210.15421.25570.051*
C7−0.04080 (18)0.10966 (10)1.0028 (13)0.0317 (9)
H7−0.06640.10681.14480.038*
C80.0077 (2)0.08534 (12)1.0283 (12)0.0442 (13)
H8A0.02720.08981.18390.053*
H8B0.03430.08920.89370.053*
C9−0.0117 (3)0.04860 (12)1.0227 (15)0.0514 (15)
H9A−0.03630.04421.16370.062*
H9B0.02070.03331.03590.062*
C10−0.0429 (3)0.04108 (12)0.7870 (14)0.0489 (16)
H10A−0.01730.04320.64690.059*
H10B−0.05700.01750.79070.059*
C11−0.0911 (2)0.06546 (12)0.7555 (15)0.0438 (12)
H11A−0.11850.06140.88640.053*
H11B−0.10940.06090.59760.053*
C12−0.0729 (2)0.10264 (11)0.7628 (15)0.0404 (11)
H12A−0.10580.11760.75360.048*
H12B−0.04880.10760.62120.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0308 (2)0.0537 (3)0.0327 (2)−0.0001 (2)0.0004 (2)−0.0078 (2)
N10.0362 (18)0.0267 (16)0.0236 (17)0.0004 (13)−0.003 (2)−0.003 (2)
C10.038 (2)0.0261 (17)0.0277 (19)0.0028 (17)−0.003 (2)−0.007 (3)
C20.062 (3)0.028 (2)0.058 (4)−0.002 (2)0.023 (3)−0.002 (2)
C30.104 (5)0.031 (2)0.044 (4)0.008 (3)0.015 (4)0.002 (2)
C40.067 (4)0.038 (3)0.056 (4)0.010 (3)0.015 (3)−0.010 (3)
C50.042 (3)0.042 (3)0.065 (4)0.007 (2)0.004 (4)−0.013 (3)
C60.032 (2)0.030 (2)0.066 (4)0.0003 (17)0.014 (3)−0.006 (3)
C70.037 (2)0.0227 (17)0.036 (2)−0.0002 (15)0.000 (3)−0.005 (2)
C80.052 (3)0.039 (2)0.042 (3)0.012 (2)−0.023 (3)−0.013 (3)
C90.070 (4)0.029 (2)0.055 (4)0.010 (2)−0.025 (4)0.000 (3)
C100.055 (3)0.026 (2)0.066 (5)0.005 (2)−0.020 (3)−0.013 (3)
C110.046 (3)0.032 (2)0.053 (3)0.0006 (19)−0.014 (4)−0.013 (3)
C120.042 (2)0.027 (2)0.052 (3)−0.0005 (18)−0.018 (3)−0.002 (3)

Geometric parameters (Å, °)

N1—C11.497 (5)C6—H6A0.99
N1—C71.512 (5)C6—H6B0.99
N1—H110.88C7—C81.520 (7)
N1—H120.88C7—C121.552 (9)
C1—C61.517 (10)C7—H71.00
C1—C21.527 (6)C8—C91.522 (7)
C1—H11.00C8—H8A0.99
C2—C31.527 (8)C8—H8B0.99
C2—H2A0.99C9—C101.525 (10)
C2—H2B0.99C9—H9A0.99
C3—C41.508 (9)C9—H9B0.99
C3—H3A0.99C10—C111.517 (7)
C3—H3B0.99C10—H10A0.99
C4—C51.503 (9)C10—H10B0.99
C4—H4A0.99C11—C121.529 (6)
C4—H4B0.99C11—H11A0.99
C5—C61.540 (6)C11—H11B0.99
C5—H5A0.99C12—H12A0.99
C5—H5B0.99C12—H12B0.99
C1—N1—C7117.5 (3)C1—C6—H6B109.7
C1—N1—H11107.9C5—C6—H6B109.7
C7—N1—H11107.9H6A—C6—H6B108.2
C1—N1—H12107.9N1—C7—C8107.9 (4)
C7—N1—H12107.9N1—C7—C12109.9 (5)
H11—N1—H12107.2C8—C7—C12110.5 (4)
N1—C1—C6110.4 (5)N1—C7—H7109.5
N1—C1—C2108.3 (4)C8—C7—H7109.5
C6—C1—C2110.4 (4)C12—C7—H7109.5
N1—C1—H1109.2C7—C8—C9111.1 (4)
C6—C1—H1109.2C7—C8—H8A109.4
C2—C1—H1109.2C9—C8—H8A109.4
C1—C2—C3110.5 (5)C7—C8—H8B109.4
C1—C2—H2A109.5C9—C8—H8B109.4
C3—C2—H2A109.5H8A—C8—H8B108.0
C1—C2—H2B109.5C8—C9—C10110.7 (5)
C3—C2—H2B109.5C8—C9—H9A109.5
H2A—C2—H2B108.1C10—C9—H9A109.5
C4—C3—C2111.0 (5)C8—C9—H9B109.5
C4—C3—H3A109.4C10—C9—H9B109.5
C2—C3—H3A109.4H9A—C9—H9B108.1
C4—C3—H3B109.4C11—C10—C9110.6 (5)
C2—C3—H3B109.4C11—C10—H10A109.5
H3A—C3—H3B108.0C9—C10—H10A109.5
C5—C4—C3112.3 (5)C11—C10—H10B109.5
C5—C4—H4A109.1C9—C10—H10B109.5
C3—C4—H4A109.1H10A—C10—H10B108.1
C5—C4—H4B109.1C10—C11—C12112.6 (4)
C3—C4—H4B109.1C10—C11—H11A109.1
H4A—C4—H4B107.9C12—C11—H11A109.1
C4—C5—C6111.6 (5)C10—C11—H11B109.1
C4—C5—H5A109.3C12—C11—H11B109.1
C6—C5—H5A109.3H11A—C11—H11B107.8
C4—C5—H5B109.3C11—C12—C7109.6 (5)
C6—C5—H5B109.3C11—C12—H12A109.7
H5A—C5—H5B108.0C7—C12—H12A109.7
C1—C6—C5109.9 (6)C11—C12—H12B109.7
C1—C6—H6A109.7C7—C12—H12B109.7
C5—C6—H6A109.7H12A—C12—H12B108.2
C7—N1—C1—C667.5 (6)C1—N1—C7—C8−175.4 (6)
C7—N1—C1—C2−171.5 (6)C1—N1—C7—C1264.0 (6)
N1—C1—C2—C3−179.5 (5)N1—C7—C8—C9−177.9 (6)
C6—C1—C2—C3−58.5 (7)C12—C7—C8—C9−57.7 (7)
C1—C2—C3—C456.2 (8)C7—C8—C9—C1057.9 (8)
C2—C3—C4—C5−54.5 (8)C8—C9—C10—C11−56.1 (8)
C3—C4—C5—C654.4 (9)C9—C10—C11—C1255.9 (9)
N1—C1—C6—C5177.4 (4)C10—C11—C12—C7−55.3 (8)
C2—C1—C6—C557.6 (6)N1—C7—C12—C11174.6 (4)
C4—C5—C6—C1−55.7 (8)C8—C7—C12—C1155.6 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H11···Br1i0.882.433.305 (5)177
N1—H12···Br10.882.433.310 (5)176

Symmetry codes: (i) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2641).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Ng, S. W. (1995). Acta Cryst. C51, 2149–2150.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography