Dicyclo­hexyl­ammonium bromide

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808023155

organic compounds

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Volume 64| Part 8| August 2008| Page o1624

doi:10.1107/S1600536808023155

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Dicyclohexylammonium bromide

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 July 2008; accepted 22 July 2008; online 31 July 2008)

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 ).

Experimental

Crystal data

C₁₂H₂₄N⁺·Br⁻
M_r = 262.23
Orthorhombic, F d d 2
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 ) 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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.139
S = 0.98
2961 reflections
127 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.56 e Å⁻³
Absolute structure: Flack (1983 ), with 1311 Friedel pairs
Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯Br1ⁱ	0.88	2.43	3.305 (5)	177
N1—H12⋯Br1	0.88	2.43	3.310 (5)	176
Symmetry code: (i) x, y, z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

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.

Dicyclohexylammonium bromide top

Crystal data top

C₁₂H₂₄N⁺·Br⁻	F(000) = 2208
M_r = 262.23	D_x = 1.336 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 3733 reflections
a = 24.1258 (4) Å	θ = 2.7–23.5°
b = 39.3926 (7) Å	µ = 3.12 mm⁻¹
c = 5.4878 (1) Å	T = 100 K
V = 5215.49 (16) Å³	Prism, colourless
Z = 16	0.40 × 0.02 × 0.02 mm

Data collection top

Bruker SMART APEXII diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
T_min = 0.368, T_max = 0.940	k = −50→50
15058 measured reflections	l = −7→6

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.1P)² + 1P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
2961 reflections	Δρ_max = 0.67 e Å⁻³
127 parameters	Δρ_min = −0.56 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 1311 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

C₁₂H₂₄N⁺·Br⁻	V = 5215.49 (16) Å³
M_r = 262.23	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 24.1258 (4) Å	µ = 3.12 mm⁻¹
b = 39.3926 (7) Å	T = 100 K
c = 5.4878 (1) Å	0.40 × 0.02 × 0.02 mm

Data collection top

Bruker SMART APEXII diffractometer	2961 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2483 reflections with I > 2σ(I)
T_min = 0.368, T_max = 0.940	R_int = 0.049
15058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.139	Δρ_max = 0.67 e Å⁻³
S = 0.98	Δρ_min = −0.56 e Å⁻³
2961 reflections	Absolute structure: Flack (1983), with 1311 Friedel pairs
127 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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

	x	y	z	U_iso*/U_eq
Br1	0.057495 (18)	0.153140 (12)	0.50000 (6)	0.03906 (17)
N1	−0.01800 (15)	0.14541 (8)	1.0006 (10)	0.0288 (7)
H11	0.0030	0.1479	1.1305	0.035*
H12	0.0036	0.1475	0.8724	0.035*
C1	−0.05883 (19)	0.17402 (9)	0.9961 (13)	0.0304 (8)
H1	−0.0854	0.1705	0.8584	0.037*
C2	−0.0271 (3)	0.20707 (12)	0.9555 (13)	0.0493 (16)
H2A	−0.0068	0.2059	0.7988	0.059*
H2B	0.0004	0.2102	1.0875	0.059*
C3	−0.0668 (4)	0.23723 (14)	0.9517 (13)	0.060 (2)
H3A	−0.0454	0.2585	0.9340	0.072*
H3B	−0.0919	0.2352	0.8098	0.072*
C4	−0.1006 (3)	0.23867 (14)	1.1826 (12)	0.0534 (17)
H4A	−0.0758	0.2438	1.3216	0.064*
H4B	−0.1280	0.2573	1.1697	0.064*
C5	−0.1307 (2)	0.20596 (13)	1.2315 (17)	0.0496 (14)
H5A	−0.1592	0.2024	1.1044	0.060*
H5B	−0.1498	0.2075	1.3909	0.060*
C6	−0.0908 (2)	0.17545 (11)	1.2338 (15)	0.0428 (12)
H6A	−0.0646	0.1776	1.3718	0.051*
H6B	−0.1121	0.1542	1.2557	0.051*
C7	−0.04080 (18)	0.10966 (10)	1.0028 (13)	0.0317 (9)
H7	−0.0664	0.1068	1.1448	0.038*
C8	0.0077 (2)	0.08534 (12)	1.0283 (12)	0.0442 (13)
H8A	0.0272	0.0898	1.1839	0.053*
H8B	0.0343	0.0892	0.8937	0.053*
C9	−0.0117 (3)	0.04860 (12)	1.0227 (15)	0.0514 (15)
H9A	−0.0363	0.0442	1.1637	0.062*
H9B	0.0207	0.0333	1.0359	0.062*
C10	−0.0429 (3)	0.04108 (12)	0.7870 (14)	0.0489 (16)
H10A	−0.0173	0.0432	0.6469	0.059*
H10B	−0.0570	0.0175	0.7907	0.059*
C11	−0.0911 (2)	0.06546 (12)	0.7555 (15)	0.0438 (12)
H11A	−0.1185	0.0614	0.8864	0.053*
H11B	−0.1094	0.0609	0.5976	0.053*
C12	−0.0729 (2)	0.10264 (11)	0.7628 (15)	0.0404 (11)
H12A	−0.1058	0.1176	0.7536	0.048*
H12B	−0.0488	0.1076	0.6212	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0308 (2)	0.0537 (3)	0.0327 (2)	−0.0001 (2)	0.0004 (2)	−0.0078 (2)
N1	0.0362 (18)	0.0267 (16)	0.0236 (17)	0.0004 (13)	−0.003 (2)	−0.003 (2)
C1	0.038 (2)	0.0261 (17)	0.0277 (19)	0.0028 (17)	−0.003 (2)	−0.007 (3)
C2	0.062 (3)	0.028 (2)	0.058 (4)	−0.002 (2)	0.023 (3)	−0.002 (2)
C3	0.104 (5)	0.031 (2)	0.044 (4)	0.008 (3)	0.015 (4)	0.002 (2)
C4	0.067 (4)	0.038 (3)	0.056 (4)	0.010 (3)	0.015 (3)	−0.010 (3)
C5	0.042 (3)	0.042 (3)	0.065 (4)	0.007 (2)	0.004 (4)	−0.013 (3)
C6	0.032 (2)	0.030 (2)	0.066 (4)	0.0003 (17)	0.014 (3)	−0.006 (3)
C7	0.037 (2)	0.0227 (17)	0.036 (2)	−0.0002 (15)	0.000 (3)	−0.005 (2)
C8	0.052 (3)	0.039 (2)	0.042 (3)	0.012 (2)	−0.023 (3)	−0.013 (3)
C9	0.070 (4)	0.029 (2)	0.055 (4)	0.010 (2)	−0.025 (4)	0.000 (3)
C10	0.055 (3)	0.026 (2)	0.066 (5)	0.005 (2)	−0.020 (3)	−0.013 (3)
C11	0.046 (3)	0.032 (2)	0.053 (3)	0.0006 (19)	−0.014 (4)	−0.013 (3)
C12	0.042 (2)	0.027 (2)	0.052 (3)	−0.0005 (18)	−0.018 (3)	−0.002 (3)

Geometric parameters (Å, º) top

N1—C1	1.497 (5)	C6—H6A	0.99
N1—C7	1.512 (5)	C6—H6B	0.99
N1—H11	0.88	C7—C8	1.520 (7)
N1—H12	0.88	C7—C12	1.552 (9)
C1—C6	1.517 (10)	C7—H7	1.00
C1—C2	1.527 (6)	C8—C9	1.522 (7)
C1—H1	1.00	C8—H8A	0.99
C2—C3	1.527 (8)	C8—H8B	0.99
C2—H2A	0.99	C9—C10	1.525 (10)
C2—H2B	0.99	C9—H9A	0.99
C3—C4	1.508 (9)	C9—H9B	0.99
C3—H3A	0.99	C10—C11	1.517 (7)
C3—H3B	0.99	C10—H10A	0.99
C4—C5	1.503 (9)	C10—H10B	0.99
C4—H4A	0.99	C11—C12	1.529 (6)
C4—H4B	0.99	C11—H11A	0.99
C5—C6	1.540 (6)	C11—H11B	0.99
C5—H5A	0.99	C12—H12A	0.99
C5—H5B	0.99	C12—H12B	0.99

C1—N1—C7	117.5 (3)	C1—C6—H6B	109.7
C1—N1—H11	107.9	C5—C6—H6B	109.7
C7—N1—H11	107.9	H6A—C6—H6B	108.2
C1—N1—H12	107.9	N1—C7—C8	107.9 (4)
C7—N1—H12	107.9	N1—C7—C12	109.9 (5)
H11—N1—H12	107.2	C8—C7—C12	110.5 (4)
N1—C1—C6	110.4 (5)	N1—C7—H7	109.5
N1—C1—C2	108.3 (4)	C8—C7—H7	109.5
C6—C1—C2	110.4 (4)	C12—C7—H7	109.5
N1—C1—H1	109.2	C7—C8—C9	111.1 (4)
C6—C1—H1	109.2	C7—C8—H8A	109.4
C2—C1—H1	109.2	C9—C8—H8A	109.4
C1—C2—C3	110.5 (5)	C7—C8—H8B	109.4
C1—C2—H2A	109.5	C9—C8—H8B	109.4
C3—C2—H2A	109.5	H8A—C8—H8B	108.0
C1—C2—H2B	109.5	C8—C9—C10	110.7 (5)
C3—C2—H2B	109.5	C8—C9—H9A	109.5
H2A—C2—H2B	108.1	C10—C9—H9A	109.5
C4—C3—C2	111.0 (5)	C8—C9—H9B	109.5
C4—C3—H3A	109.4	C10—C9—H9B	109.5
C2—C3—H3A	109.4	H9A—C9—H9B	108.1
C4—C3—H3B	109.4	C11—C10—C9	110.6 (5)
C2—C3—H3B	109.4	C11—C10—H10A	109.5
H3A—C3—H3B	108.0	C9—C10—H10A	109.5
C5—C4—C3	112.3 (5)	C11—C10—H10B	109.5
C5—C4—H4A	109.1	C9—C10—H10B	109.5
C3—C4—H4A	109.1	H10A—C10—H10B	108.1
C5—C4—H4B	109.1	C10—C11—C12	112.6 (4)
C3—C4—H4B	109.1	C10—C11—H11A	109.1
H4A—C4—H4B	107.9	C12—C11—H11A	109.1
C4—C5—C6	111.6 (5)	C10—C11—H11B	109.1
C4—C5—H5A	109.3	C12—C11—H11B	109.1
C6—C5—H5A	109.3	H11A—C11—H11B	107.8
C4—C5—H5B	109.3	C11—C12—C7	109.6 (5)
C6—C5—H5B	109.3	C11—C12—H12A	109.7
H5A—C5—H5B	108.0	C7—C12—H12A	109.7
C1—C6—C5	109.9 (6)	C11—C12—H12B	109.7
C1—C6—H6A	109.7	C7—C12—H12B	109.7
C5—C6—H6A	109.7	H12A—C12—H12B	108.2

C7—N1—C1—C6	67.5 (6)	C1—N1—C7—C8	−175.4 (6)
C7—N1—C1—C2	−171.5 (6)	C1—N1—C7—C12	64.0 (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—C4	56.2 (8)	C7—C8—C9—C10	57.9 (8)
C2—C3—C4—C5	−54.5 (8)	C8—C9—C10—C11	−56.1 (8)
C3—C4—C5—C6	54.4 (9)	C9—C10—C11—C12	55.9 (9)
N1—C1—C6—C5	177.4 (4)	C10—C11—C12—C7	−55.3 (8)
C2—C1—C6—C5	57.6 (6)	N1—C7—C12—C11	174.6 (4)
C4—C5—C6—C1	−55.7 (8)	C8—C7—C12—C11	55.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···Br1ⁱ	0.88	2.43	3.305 (5)	177
N1—H12···Br1	0.88	2.43	3.310 (5)	176

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

Experimental details

Crystal data
Chemical formula	C₁₂H₂₄N⁺·Br⁻
M_r	262.23
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	100
a, b, c (Å)	24.1258 (4), 39.3926 (7), 5.4878 (1)
V (Å³)	5215.49 (16)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	3.12
Crystal size (mm)	0.40 × 0.02 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.368, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	15058, 2961, 2483
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.139, 0.98
No. of reflections	2961
No. of parameters	127
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.56
Absolute structure	Flack (1983), with 1311 Friedel pairs
Absolute structure parameter	0.01 (2)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···Br1ⁱ	0.88	2.43	3.305 (5)	177
N1—H12···Br1	0.88	2.43	3.310 (5)	176

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

Acknowledgements

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.

References

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