Diisopropyl-ammonium nitrite.

In the title mol-ecular salt, C(6)H(16)N(+)·NO(2) (-), the cation forms two N-H⋯O hydrogen bonds to nearby nitrite anions which link the ionic units into chains propagating along the b-axis direction.

Related literature

For a related structure, see: Xu (2012 ▶). For background to mol­ecular ferroelectric compounds, see: Fu et al. (2011 ▶).

Experimental

Crystal data

C6H16N+·NO2 −

M = 148.21

Monoclinic,

a = 8.2314 (16) Å

b = 7.7466 (15) Å

c = 14.583 (3) Å

β = 94.16 (3)°

V = 927.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

9189 measured reflections

2127 independent reflections

1130 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.285

S = 1.07

2127 reflections

95 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.32 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/S1600536812008574/hb6657sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008574/hb6657Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008574/hb6657Isup3.cml

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

C6H16N+·NO2−	F(000) = 328
Mr = 148.21	Dx = 1.061 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2127 reflections
a = 8.2314 (16) Å	θ = 3.6–27.5°
b = 7.7466 (15) Å	µ = 0.08 mm−1
c = 14.583 (3) Å	T = 298 K
β = 94.16 (3)°	Block, colourless
V = 927.5 (3) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 CCD diffractometer	2127 independent reflections
Radiation source: fine-focus sealed tube	1130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.6°
CCD profile fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.910, Tmax = 1.000	l = −18→18
9189 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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.285	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1379P)2 + 0.0979P] where P = (Fo2 + 2Fc2)/3
2127 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.50 e Å−3
15 restraints	Δρmin = −0.32 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 > 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
N1	0.6713 (3)	0.1958 (3)	0.35567 (15)	0.0543 (7)
H1D	0.6950	0.0825	0.3543	0.065*
H1E	0.6890	0.2393	0.3000	0.065*
C2	0.4930 (4)	0.2132 (4)	0.3690 (2)	0.0624 (9)
H2A	0.4733	0.1702	0.4304	0.075*
O1	0.7263 (3)	0.3533 (3)	0.18791 (17)	0.0931 (9)
C5	0.7889 (4)	0.2792 (4)	0.4247 (2)	0.0686 (9)
H5A	0.7676	0.4037	0.4255	0.082*
N2	0.7438 (4)	0.2425 (4)	0.1320 (2)	0.0925 (9)
O2	0.8050 (4)	0.2847 (5)	0.0648 (2)	0.1177 (10)
C6	0.7724 (5)	0.2066 (6)	0.5196 (2)	0.0918 (12)
H6A	0.6642	0.2277	0.5376	0.138*
H6B	0.8500	0.2614	0.5626	0.138*
H6C	0.7925	0.0846	0.5192	0.138*
C3	0.3999 (4)	0.1012 (6)	0.2986 (3)	0.0909 (12)
H3A	0.4409	−0.0148	0.3032	0.136*
H3B	0.4133	0.1453	0.2381	0.136*
H3C	0.2865	0.1017	0.3099	0.136*
C4	0.9579 (5)	0.2488 (7)	0.3938 (3)	0.1037 (14)
H4A	0.9700	0.3099	0.3374	0.156*
H4B	0.9736	0.1275	0.3841	0.156*
H4C	1.0374	0.2895	0.4402	0.156*
C1	0.4425 (5)	0.3998 (5)	0.3631 (3)	0.0941 (13)
H1A	0.5025	0.4643	0.4104	0.141*
H1B	0.3280	0.4089	0.3710	0.141*
H1C	0.4646	0.4452	0.3040	0.141*

	U11	U22	U33	U12	U13	U23
N1	0.0532 (15)	0.0552 (13)	0.0547 (13)	0.0026 (10)	0.0053 (10)	0.0051 (10)
C2	0.0558 (19)	0.0711 (19)	0.0611 (17)	0.0005 (14)	0.0101 (14)	0.0032 (14)
O1	0.1178 (19)	0.0879 (17)	0.0762 (14)	0.0013 (13)	0.0258 (13)	0.0032 (11)
C5	0.063 (2)	0.0582 (17)	0.082 (2)	−0.0024 (14)	−0.0121 (16)	0.0038 (15)
N2	0.116 (2)	0.0955 (18)	0.0689 (15)	0.0076 (14)	0.0293 (14)	−0.0001 (13)
O2	0.145 (2)	0.126 (2)	0.0854 (16)	0.0130 (16)	0.0308 (15)	0.0006 (14)
C6	0.102 (3)	0.110 (3)	0.061 (2)	0.003 (2)	−0.0109 (18)	−0.005 (2)
C3	0.061 (2)	0.114 (3)	0.097 (3)	−0.0143 (19)	0.0022 (19)	−0.014 (2)
C4	0.056 (2)	0.142 (4)	0.111 (3)	−0.011 (2)	−0.003 (2)	0.025 (3)
C1	0.068 (2)	0.089 (3)	0.125 (3)	0.0240 (19)	0.006 (2)	0.003 (2)

N1—C5	1.492 (4)	C6—H6A	0.9600
N1—C2	1.500 (4)	C6—H6B	0.9600
N1—H1D	0.9000	C6—H6C	0.9600
N1—H1E	0.9000	C3—H3A	0.9600
C2—C1	1.505 (5)	C3—H3B	0.9600
C2—C3	1.509 (5)	C3—H3C	0.9600
C2—H2A	0.9800	C4—H4A	0.9600
O1—N2	1.200 (4)	C4—H4B	0.9600
C5—C6	1.510 (5)	C4—H4C	0.9600
C5—C4	1.512 (5)	C1—H1A	0.9600
C5—H5A	0.9800	C1—H1B	0.9600
N2—O2	1.181 (4)	C1—H1C	0.9600
C5—N1—C2	117.8 (2)	C5—C6—H6C	109.5
C5—N1—H1D	107.9	H6A—C6—H6C	109.5
C2—N1—H1D	107.9	H6B—C6—H6C	109.5
C5—N1—H1E	107.9	C2—C3—H3A	109.5
C2—N1—H1E	107.9	C2—C3—H3B	109.5
H1D—N1—H1E	107.2	H3A—C3—H3B	109.5
N1—C2—C1	110.4 (3)	C2—C3—H3C	109.5
N1—C2—C3	108.2 (2)	H3A—C3—H3C	109.5
C1—C2—C3	112.9 (3)	H3B—C3—H3C	109.5
N1—C2—H2A	108.4	C5—C4—H4A	109.5
C1—C2—H2A	108.4	C5—C4—H4B	109.5
C3—C2—H2A	108.4	H4A—C4—H4B	109.5
N1—C5—C6	111.1 (3)	C5—C4—H4C	109.5
N1—C5—C4	107.3 (3)	H4A—C4—H4C	109.5
C6—C5—C4	111.2 (3)	H4B—C4—H4C	109.5
N1—C5—H5A	109.1	C2—C1—H1A	109.5
C6—C5—H5A	109.1	C2—C1—H1B	109.5
C4—C5—H5A	109.1	H1A—C1—H1B	109.5
O2—N2—O1	116.4 (4)	C2—C1—H1C	109.5
C5—C6—H6A	109.5	H1A—C1—H1C	109.5
C5—C6—H6B	109.5	H1B—C1—H1C	109.5
H6A—C6—H6B	109.5
C5—N1—C2—C1	63.0 (3)	C2—N1—C5—C6	60.4 (3)
C5—N1—C2—C3	−173.0 (3)	C2—N1—C5—C4	−177.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1E···O1	0.90	1.90	2.800 (3)	174
N1—H1D···O1i	0.90	2.00	2.869 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1E⋯O1	0.90	1.90	2.800 (3)	174
N1—H1D⋯O1i	0.90	2.00	2.869 (3)	161

Symmetry code: (i) .