Diisopropyl-ammonium thio-cyanate.

In the title mol-ecular salt, C(6)H(16)N(+)·NCS(-), the cation possesses approximate local twofold rotation symmetry. One of its NH atoms forms a hydrogen bond to a thio-cyanate N atom and the other to a thio-cyanate S atom. This results in [001] chains of alternating cations and anions.

Related literature

For background to mol­ecular ferroelectrics, see: Fu et al. (2011 ▶).

Experimental

Crystal data

C6H16N+·NCS−

M = 160.28

Orthorhombic,

a = 11.785 (2) Å

b = 12.716 (3) Å

c = 13.288 (3) Å

V = 1991.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 298 K

0.20 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.90, T max = 1.00

19260 measured reflections

2286 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.107

S = 1.12

2286 reflections

96 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007349/hb6639sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007349/hb6639Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007349/hb6639Isup3.cml

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

C6H16N+·NCS−	F(000) = 704
Mr = 160.28	Dx = 1.069 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2286 reflections
a = 11.785 (2) Å	θ = 3.1–27.5°
b = 12.716 (3) Å	µ = 0.27 mm−1
c = 13.288 (3) Å	T = 298 K
V = 1991.3 (7) Å3	Block, colourless
Z = 8	0.20 × 0.05 × 0.05 mm

Rigaku Mercury2 CCD diffractometer	2286 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.90, Tmax = 1.00	l = −17→17
19260 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0402P)2 + 0.4971P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2286 reflections	Δρmax = 0.18 e Å−3
96 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (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 > 2sigma(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
N2	0.42899 (11)	0.17785 (9)	0.36893 (10)	0.0400 (3)
H2D	0.3915	0.2112	0.3193	0.048*
H2E	0.3769	0.1567	0.4141	0.048*
C3	0.48334 (15)	0.08132 (13)	0.32473 (13)	0.0476 (4)
H3A	0.5226	0.0434	0.3787	0.057*
C5	0.57312 (16)	0.20499 (14)	0.50250 (15)	0.0551 (5)
H5A	0.6217	0.1522	0.4741	0.083*
H5B	0.5224	0.1729	0.5500	0.083*
H5C	0.6184	0.2571	0.5361	0.083*
C6	0.50507 (15)	0.25665 (13)	0.41958 (13)	0.0471 (4)
H6A	0.5578	0.2850	0.3694	0.056*
C7	0.4316 (2)	0.34550 (15)	0.45802 (16)	0.0666 (6)
H7A	0.3883	0.3743	0.4033	0.100*
H7B	0.4788	0.3994	0.4864	0.100*
H7C	0.3809	0.3193	0.5087	0.100*
C4	0.3906 (2)	0.01151 (17)	0.28384 (17)	0.0727 (6)
H4A	0.4231	−0.0530	0.2598	0.109*
H4B	0.3527	0.0467	0.2294	0.109*
H4C	0.3369	−0.0036	0.3363	0.109*
C2	0.5690 (2)	0.1114 (2)	0.24603 (18)	0.0774 (7)
H2A	0.6292	0.1508	0.2768	0.116*
H2B	0.5330	0.1536	0.1954	0.116*
H2C	0.5996	0.0490	0.2157	0.116*
S1	0.26970 (4)	0.06903 (3)	0.54981 (3)	0.04839 (18)
N1	0.32617 (17)	0.20204 (15)	0.70857 (14)	0.0754 (6)
C1	0.30276 (14)	0.14704 (14)	0.64316 (13)	0.0459 (4)

	U11	U22	U33	U12	U13	U23
N2	0.0425 (7)	0.0407 (7)	0.0369 (7)	0.0020 (6)	−0.0008 (6)	0.0052 (6)
C3	0.0555 (10)	0.0441 (9)	0.0432 (9)	0.0098 (8)	−0.0096 (8)	−0.0048 (7)
C5	0.0523 (10)	0.0544 (11)	0.0586 (11)	−0.0096 (8)	−0.0106 (9)	−0.0078 (9)
C6	0.0553 (10)	0.0370 (8)	0.0489 (9)	−0.0081 (7)	0.0062 (8)	0.0020 (7)
C7	0.0863 (15)	0.0420 (10)	0.0714 (14)	0.0048 (10)	0.0026 (11)	−0.0043 (9)
C4	0.0806 (15)	0.0675 (13)	0.0700 (14)	−0.0024 (11)	−0.0161 (11)	−0.0230 (11)
C2	0.0745 (15)	0.0887 (16)	0.0690 (14)	0.0145 (12)	0.0166 (11)	−0.0150 (13)
S1	0.0527 (3)	0.0463 (3)	0.0462 (3)	−0.00456 (19)	0.00129 (19)	−0.00236 (19)
N1	0.0879 (14)	0.0808 (12)	0.0576 (11)	−0.0223 (11)	−0.0029 (9)	−0.0157 (9)
C1	0.0422 (9)	0.0503 (10)	0.0451 (9)	−0.0037 (7)	0.0023 (7)	0.0037 (8)

N2—C6	1.504 (2)	C6—H6A	0.9800
N2—C3	1.504 (2)	C7—H7A	0.9600
N2—H2D	0.9000	C7—H7B	0.9600
N2—H2E	0.9000	C7—H7C	0.9600
C3—C2	1.503 (3)	C4—H4A	0.9600
C3—C4	1.509 (3)	C4—H4B	0.9600
C3—H3A	0.9800	C4—H4C	0.9600
C5—C6	1.513 (2)	C2—H2A	0.9600
C5—H5A	0.9600	C2—H2B	0.9600
C5—H5B	0.9600	C2—H2C	0.9600
C5—H5C	0.9600	S1—C1	1.6354 (19)
C6—C7	1.512 (3)	N1—C1	1.149 (2)
C6—N2—C3	117.69 (13)	C7—C6—H6A	108.6
C6—N2—H2D	107.9	C5—C6—H6A	108.6
C3—N2—H2D	107.9	C6—C7—H7A	109.5
C6—N2—H2E	107.9	C6—C7—H7B	109.5
C3—N2—H2E	107.9	H7A—C7—H7B	109.5
H2D—N2—H2E	107.2	C6—C7—H7C	109.5
C2—C3—N2	110.49 (15)	H7A—C7—H7C	109.5
C2—C3—C4	112.70 (17)	H7B—C7—H7C	109.5
N2—C3—C4	108.19 (15)	C3—C4—H4A	109.5
C2—C3—H3A	108.5	C3—C4—H4B	109.5
N2—C3—H3A	108.5	H4A—C4—H4B	109.5
C4—C3—H3A	108.5	C3—C4—H4C	109.5
C6—C5—H5A	109.5	H4A—C4—H4C	109.5
C6—C5—H5B	109.5	H4B—C4—H4C	109.5
H5A—C5—H5B	109.5	C3—C2—H2A	109.5
C6—C5—H5C	109.5	C3—C2—H2B	109.5
H5A—C5—H5C	109.5	H2A—C2—H2B	109.5
H5B—C5—H5C	109.5	C3—C2—H2C	109.5
N2—C6—C7	107.91 (15)	H2A—C2—H2C	109.5
N2—C6—C5	110.65 (13)	H2B—C2—H2C	109.5
C7—C6—C5	112.46 (16)	N1—C1—S1	179.8 (2)
N2—C6—H6A	108.6
C6—N2—C3—C2	−59.45 (19)	C3—N2—C6—C7	−179.73 (14)
C6—N2—C3—C4	176.74 (15)	C3—N2—C6—C5	−56.31 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2D···N1i	0.90	1.99	2.888 (2)	172
N2—H2E···S1	0.90	2.47	3.3490 (14)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2D⋯N1i	0.90	1.99	2.888 (2)	172
N2—H2E⋯S1	0.90	2.47	3.3490 (14)	166

Symmetry code: (i) .