Crystal structure of cyclo-hexyl-ammonium thio-cyanate.

In the title salt, C6H11NH3 (+)·SCN(-), the cyclo-hexyl-ammonium ring adopts a slightly distorted chair conformation. The ammonium group occupies an equatorial position to minimize 1,3 and 1,5 diaxial inter-actions. In the crystal, the components are linked by N-H⋯N and N-H⋯S hydrogen-bonding inter-actions, resulting in a three-dimensional network.

Related literature

For the synthesis and uses of the title compound, see: Baluja et al. (1960 ▸); Coddens et al. (1986 ▸); Goel (1988 ▸); Mathes et al. (1948 ▸) 1955 ▸); Mathes & Stewart (1955 ▸); Morrison & Ratcliffe (1953 ▸); Stewart (1951 ▸); For the structures of other cyclo­hexyl­ammonium salts, see: Bagabas et al. (2014 ▸); Shimada et al. (1955 ▸); Smith et al. (1994 ▸); Odendal et al. (2010 ▸).

Experimental

Crystal data

C6H14N+·NCS−

M = 158.26

Trigonal,

a = 23.4036 (6) Å

c = 8.3373 (2) Å

V = 3954.8 (2) Å3

Z = 18

Cu Kα radiation

μ = 2.71 mm−1

T = 296 K

0.98 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.176, T max = 0.748

10355 measured reflections

1670 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.06

1670 reflections

103 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989014027297/sj5432sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027297/sj5432Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027297/sj5432Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027297/sj5432fig1.tif

The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. The strong N—H⋯N hydrogen bond linking the cation and the anion is shown as a dashed line.

Click here for additional data file.

. DOI: 10.1107/S2056989014027297/sj5432fig2.tif

Crystal packing of the title compound, showing the N–H⋯N and N–H⋯S hydrogen bonding inter­actions (see Table 1) as dashed lines producing a three-dimensional network

CCDC reference: 1039130

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H14N+·NCS−	Dx = 1.196 Mg m−3
Mr = 158.26	Cu Kα radiation, λ = 1.54178 Å
Trigonal, R3:H	Cell parameters from 3689 reflections
a = 23.4036 (6) Å	θ = 3.8–71.3°
c = 8.3373 (2) Å	µ = 2.71 mm−1
V = 3954.8 (2) Å3	T = 296 K
Z = 18	Needle, colourless
F(000) = 1548	0.98 × 0.25 × 0.11 mm

Bruker APEXII CCD diffractometer	1530 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.051
Absorption correction: multi-scan (SADABS; Bruker, 2009)	θmax = 72.1°, θmin = 3.8°
Tmin = 0.176, Tmax = 0.748	h = −28→28
10355 measured reflections	k = −28→28
1670 independent reflections	l = −7→9

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0622P)2 + 1.6831P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1670 reflections	Δρmax = 0.22 e Å−3
103 parameters	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.06708 (2)	0.40416 (2)	0.39763 (4)	0.04932 (18)
N1	0.22496 (6)	0.30544 (6)	0.62467 (16)	0.0396 (3)
N2	0.15453 (8)	0.36894 (8)	0.5327 (2)	0.0628 (4)
C1	0.17544 (6)	0.24495 (6)	0.71255 (15)	0.0339 (3)
H1A	0.1541	0.2582	0.7939	0.041*
C2	0.12316 (7)	0.19773 (7)	0.59728 (17)	0.0433 (3)
H2A	0.1437	0.1862	0.5119	0.052*
H2B	0.1005	0.2187	0.5496	0.052*
C3	0.07361 (7)	0.13543 (8)	0.6863 (2)	0.0525 (4)
H3A	0.0494	0.1465	0.7626	0.063*
H3B	0.0422	0.1041	0.6102	0.063*
C4	0.10721 (9)	0.10360 (7)	0.7747 (2)	0.0570 (4)
H4A	0.1264	0.0871	0.6973	0.068*
H4B	0.0746	0.0664	0.8364	0.068*
C5	0.16092 (8)	0.15210 (8)	0.88648 (19)	0.0502 (4)
H5A	0.1836	0.1312	0.9345	0.060*
H5B	0.1410	0.1643	0.9721	0.060*
C6	0.21055 (7)	0.21389 (7)	0.79664 (18)	0.0422 (3)
H6A	0.2427	0.2452	0.8715	0.051*
H6B	0.2339	0.2025	0.7184	0.051*
C7	0.11856 (7)	0.38340 (7)	0.47760 (17)	0.0426 (3)
H3N	0.2412 (9)	0.2942 (10)	0.545 (2)	0.055 (5)*
H2N	0.2062 (9)	0.3280 (9)	0.587 (2)	0.046 (4)*
H1N	0.2572 (10)	0.3321 (10)	0.691 (3)	0.061 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0485 (2)	0.0679 (3)	0.0414 (3)	0.03650 (19)	0.00383 (14)	0.00618 (15)
N1	0.0367 (6)	0.0371 (6)	0.0419 (7)	0.0162 (5)	−0.0010 (5)	0.0025 (5)
N2	0.0598 (8)	0.0673 (9)	0.0734 (10)	0.0408 (8)	−0.0064 (7)	0.0012 (7)
C1	0.0320 (6)	0.0350 (6)	0.0344 (7)	0.0165 (5)	0.0010 (5)	0.0007 (5)
C2	0.0362 (7)	0.0460 (7)	0.0398 (8)	0.0145 (6)	−0.0040 (5)	−0.0015 (6)
C3	0.0374 (7)	0.0488 (8)	0.0518 (9)	0.0070 (6)	0.0015 (6)	−0.0043 (7)
C4	0.0615 (9)	0.0362 (7)	0.0624 (10)	0.0162 (7)	0.0150 (8)	0.0050 (7)
C5	0.0567 (9)	0.0488 (8)	0.0500 (9)	0.0299 (7)	0.0048 (7)	0.0119 (6)
C6	0.0379 (7)	0.0437 (7)	0.0469 (8)	0.0218 (6)	−0.0034 (6)	0.0032 (6)
C7	0.0416 (7)	0.0437 (7)	0.0417 (8)	0.0207 (6)	0.0031 (6)	−0.0006 (6)

S1—C7	1.6486 (15)	C3—C4	1.517 (3)
N1—C1	1.4978 (16)	C3—H3A	0.9700
N1—H3N	0.87 (2)	C3—H3B	0.9700
N1—H2N	0.90 (2)	C4—C5	1.520 (2)
N1—H1N	0.89 (2)	C4—H4A	0.9700
N2—C7	1.148 (2)	C4—H4B	0.9700
C1—C2	1.5132 (18)	C5—C6	1.524 (2)
C1—C6	1.5142 (18)	C5—H5A	0.9700
C1—H1A	0.9800	C5—H5B	0.9700
C2—C3	1.527 (2)	C6—H6A	0.9700
C2—H2A	0.9700	C6—H6B	0.9700
C2—H2B	0.9700
C1—N1—H3N	109.8 (13)	C2—C3—H3B	109.2
C1—N1—H2N	110.7 (11)	H3A—C3—H3B	107.9
H3N—N1—H2N	108.9 (17)	C3—C4—C5	111.65 (13)
C1—N1—H1N	109.9 (13)	C3—C4—H4A	109.3
H3N—N1—H1N	110.1 (18)	C5—C4—H4A	109.3
H2N—N1—H1N	107.5 (16)	C3—C4—H4B	109.3
N1—C1—C2	109.91 (11)	C5—C4—H4B	109.3
N1—C1—C6	109.33 (11)	H4A—C4—H4B	108.0
C2—C1—C6	112.22 (11)	C4—C5—C6	111.14 (13)
N1—C1—H1A	108.4	C4—C5—H5A	109.4
C2—C1—H1A	108.4	C6—C5—H5A	109.4
C6—C1—H1A	108.4	C4—C5—H5B	109.4
C1—C2—C3	109.83 (11)	C6—C5—H5B	109.4
C1—C2—H2A	109.7	H5A—C5—H5B	108.0
C3—C2—H2A	109.7	C1—C6—C5	110.12 (11)
C1—C2—H2B	109.7	C1—C6—H6A	109.6
C3—C2—H2B	109.7	C5—C6—H6A	109.6
H2A—C2—H2B	108.2	C1—C6—H6B	109.6
C4—C3—C2	111.86 (13)	C5—C6—H6B	109.6
C4—C3—H3A	109.2	H6A—C6—H6B	108.2
C2—C3—H3A	109.2	N2—C7—S1	179.71 (16)
C4—C3—H3B	109.2
N1—C1—C2—C3	178.72 (12)	C3—C4—C5—C6	−54.67 (18)
C6—C1—C2—C3	56.83 (16)	N1—C1—C6—C5	−179.85 (12)
C1—C2—C3—C4	−54.73 (17)	C2—C1—C6—C5	−57.63 (16)
C2—C3—C4—C5	54.43 (18)	C4—C5—C6—C1	55.66 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1i	0.89 (2)	2.62 (2)	3.4955 (14)	167 (2)
N1—H2N···N2	0.90 (2)	1.94 (2)	2.822 (2)	170.4 (18)
N1—H3N···S1ii	0.87 (2)	2.573 (18)	3.4214 (14)	165.5 (19)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1NS1i	0.89(2)	2.62(2)	3.4955(14)	167(2)
N1H2NN2	0.90(2)	1.94(2)	2.822(2)	170.4(18)
N1H3NS1ii	0.87(2)	2.573(18)	3.4214(14)	165.5(19)

Symmetry codes: (i) ; (ii) .