2-Amino-cyclo-hexan-1-aminium thio-cyanate.

The title compound, C(6)H(15)N(2) (+)·NCS(-), was obtained unexpectedly from the reaction mixture of benzoyl chloride, ammonium thio-cyanate and cyclo-hexane-1,2-diamine. The cyclo-hexane ring adopts a chair conformation. In the crystal, N-H⋯S and N-H⋯N inter-actions involving the thio-cyanate anion and both the amine and the aminium N atoms link the mol-ecules, forming two-dimensional networks parallel to (001).

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related thio­cyanate structures, see: Selvakumaran et al. (2011 ▶); Khawar Rauf et al. (2008 ▶).

Experimental

Crystal data

C6H15N2 +·NCS−

M = 173.28

Orthorhombic,

a = 8.590 (3) Å

b = 12.885 (5) Å

c = 17.237 (7) Å

V = 1907.8 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.50 × 0.50 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.870, T max = 0.932

10172 measured reflections

1685 independent reflections

1449 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.14

1685 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker,2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020879/lr2062sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020879/lr2062Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020879/lr2062Isup3.cml

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

C6H15N2+·NCS−	F(000) = 752
Mr = 173.28	Dx = 1.207 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2210 reflections
a = 8.590 (3) Å	θ = 3.0–25.0°
b = 12.885 (5) Å	µ = 0.29 mm−1
c = 17.237 (7) Å	T = 298 K
V = 1907.8 (13) Å3	Block, colourless
Z = 8	0.50 × 0.50 × 0.25 mm

Bruker SMART APEX CCD area-detector diffractometer	1685 independent reflections
Radiation source: fine-focus sealed tube	1449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 83.66 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −15→12
Tmin = 0.870, Tmax = 0.932	l = −20→18
10172 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.051P)2 + 0.6001P] where P = (Fo2 + 2Fc2)/3
1685 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
N1	0.87938 (18)	0.27887 (13)	0.03084 (9)	0.0437 (4)
H1A	0.9431	0.3073	0.0637	0.052*
H1B	0.8343	0.3242	0.0065	0.052*
H1C	0.9375	0.2357	−0.0090	0.052*
N2	0.55776 (18)	0.33551 (13)	0.07851 (9)	0.0436 (4)
H2A	0.6130	0.3926	0.0516	0.052*
H2B	0.4757	0.3638	0.1112	0.052*
C1	0.7706 (2)	0.20856 (14)	0.07357 (10)	0.0354 (4)
H1D	0.7077	0.1708	0.0355	0.043*
C2	0.8674 (2)	0.13050 (15)	0.11858 (12)	0.0433 (5)
H2C	0.9300	0.0902	0.0827	0.052*
H2D	0.9374	0.1671	0.1532	0.052*
C3	0.7648 (3)	0.05792 (16)	0.16548 (12)	0.0493 (5)
H3A	0.7022	0.0162	0.1305	0.059*
H3B	0.8297	0.0114	0.1957	0.059*
C4	0.6591 (3)	0.11804 (17)	0.21932 (12)	0.0513 (5)
H4A	0.7213	0.1539	0.2579	0.062*
H4B	0.5904	0.0703	0.2462	0.062*
C5	0.5629 (2)	0.19625 (16)	0.17426 (11)	0.0463 (5)
H5A	0.5010	0.2366	0.2104	0.056*
H5B	0.4919	0.1593	0.1403	0.056*
C6	0.6618 (2)	0.26985 (14)	0.12574 (10)	0.0371 (4)
H6A	0.7235	0.3141	0.1603	0.045*
S1	0.15812 (8)	0.37823 (5)	0.14873 (3)	0.0610 (2)
N3	0.2362 (3)	0.53658 (16)	0.04577 (11)	0.0678 (6)
C7	0.2023 (2)	0.47221 (16)	0.08883 (11)	0.0443 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0428 (9)	0.0436 (9)	0.0446 (9)	0.0029 (7)	0.0051 (7)	0.0088 (7)
N2	0.0366 (8)	0.0421 (9)	0.0520 (10)	0.0063 (7)	0.0000 (7)	0.0027 (7)
C1	0.0349 (9)	0.0353 (10)	0.0361 (9)	−0.0039 (8)	0.0002 (7)	0.0009 (8)
C2	0.0421 (11)	0.0409 (11)	0.0469 (11)	0.0055 (9)	0.0019 (9)	0.0032 (9)
C3	0.0586 (13)	0.0400 (11)	0.0493 (11)	0.0026 (10)	0.0020 (10)	0.0085 (9)
C4	0.0582 (13)	0.0522 (13)	0.0435 (11)	−0.0042 (10)	0.0079 (10)	0.0075 (9)
C5	0.0408 (10)	0.0531 (12)	0.0451 (10)	−0.0008 (9)	0.0078 (8)	−0.0006 (9)
C6	0.0366 (10)	0.0366 (10)	0.0383 (9)	−0.0002 (8)	−0.0025 (8)	−0.0029 (8)
S1	0.0708 (4)	0.0589 (4)	0.0535 (4)	−0.0088 (3)	0.0002 (3)	0.0116 (3)
N3	0.0815 (15)	0.0521 (12)	0.0697 (12)	0.0012 (11)	0.0043 (11)	0.0167 (11)
C7	0.0420 (11)	0.0442 (12)	0.0467 (11)	0.0070 (9)	−0.0023 (9)	−0.0063 (10)

N1—C1	1.495 (2)	C3—C4	1.512 (3)
N1—H1A	0.8682	C3—H3A	0.9700
N1—H1B	0.8173	C3—H3B	0.9700
N1—H1C	1.0147	C4—C5	1.517 (3)
N2—C6	1.475 (2)	C4—H4A	0.9700
N2—H2A	0.9911	C4—H4B	0.9700
N2—H2B	0.9740	C5—C6	1.523 (3)
C1—C2	1.518 (3)	C5—H5A	0.9700
C1—C6	1.519 (2)	C5—H5B	0.9700
C1—H1D	0.9800	C6—H6A	0.9800
C2—C3	1.518 (3)	S1—C7	1.636 (2)
C2—H2C	0.9700	N3—C7	1.150 (3)
C2—H2D	0.9700
C1—N1—H1A	109.2	C2—C3—H3A	109.4
C1—N1—H1B	112.9	C4—C3—H3B	109.4
H1A—N1—H1B	109.4	C2—C3—H3B	109.4
C1—N1—H1C	108.0	H3A—C3—H3B	108.0
H1A—N1—H1C	111.2	C3—C4—C5	110.68 (17)
H1B—N1—H1C	106.1	C3—C4—H4A	109.5
C6—N2—H2A	113.2	C5—C4—H4A	109.5
C6—N2—H2B	109.5	C3—C4—H4B	109.5
H2A—N2—H2B	109.9	C5—C4—H4B	109.5
N1—C1—C2	108.11 (15)	H4A—C4—H4B	108.1
N1—C1—C6	111.17 (15)	C4—C5—C6	113.01 (16)
C2—C1—C6	112.27 (15)	C4—C5—H5A	109.0
N1—C1—H1D	108.4	C6—C5—H5A	109.0
C2—C1—H1D	108.4	C4—C5—H5B	109.0
C6—C1—H1D	108.4	C6—C5—H5B	109.0
C3—C2—C1	111.24 (17)	H5A—C5—H5B	107.8
C3—C2—H2C	109.4	N2—C6—C1	110.14 (15)
C1—C2—H2C	109.4	N2—C6—C5	108.79 (15)
C3—C2—H2D	109.4	C1—C6—C5	110.16 (15)
C1—C2—H2D	109.4	N2—C6—H6A	109.2
H2C—C2—H2D	108.0	C1—C6—H6A	109.2
C4—C3—C2	111.09 (17)	C5—C6—H6A	109.2
C4—C3—H3A	109.4	N3—C7—S1	178.2 (2)
N1—C1—C2—C3	178.41 (15)	C2—C1—C6—N2	−173.39 (15)
C6—C1—C2—C3	55.4 (2)	N1—C1—C6—C5	−174.63 (15)
C1—C2—C3—C4	−56.1 (2)	C2—C1—C6—C5	−53.4 (2)
C2—C3—C4—C5	55.6 (2)	C4—C5—C6—N2	174.46 (16)
C3—C4—C5—C6	−55.2 (2)	C4—C5—C6—C1	53.6 (2)
N1—C1—C6—N2	65.36 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.87	2.53	3.3914 (19)	172
N1—H1B···N3ii	0.82	2.10	2.895 (3)	166
N1—H1C···N2iii	1.01	1.83	2.841 (2)	175
N2—H2A···N3ii	0.99	2.31	3.231 (3)	155
N2—H2B···S1	0.97	2.81	3.681 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.87	2.53	3.3914 (19)	172
N1—H1B⋯N3ii	0.82	2.10	2.895 (3)	166
N1—H1C⋯N2iii	1.01	1.83	2.841 (2)	175
N2—H2A⋯N3ii	0.99	2.31	3.231 (3)	155
N2—H2B⋯S1	0.97	2.81	3.681 (2)	149

Symmetry codes: (i) ; (ii) ; (iii) .