Dicyclo-hexyl-ammonium bromide.

In the title compound, C(12)H(24)N(+)·Br(-), both cyclo-hexane 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 = 262.23

Orthorhombic,

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[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 ▶), with 1311 Friedel pairs

Flack parameter: 0.01 (2)

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 ▶).

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

C12H24N+·Br–	F000 = 2208
Mr = 262.23	Dx = 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 = 2.7–23.5º
b = 39.3926 (7) Å	µ = 3.12 mm−1
c = 5.4878 (1) Å	T = 100 (2) K
V = 5215.49 (16) Å3	Prism, colourless
Z = 16	0.40 × 0.02 × 0.02 mm

Bruker SMART APEXII diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −31→31
Tmin = 0.368, Tmax = 0.940	k = −50→50
15058 measured reflections	l = −7→6

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 0.98	Δρmax = 0.67 e Å−3
2961 reflections	Δρmin = −0.56 e Å−3
127 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), with 1311 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .