N,N-Bis(cyano-meth-yl)nitrous amide.

In the title compound, C(4)H(4)N(4)O, both H atoms bonded to one methyl-ene C atom are involved in C-H⋯N hydrogen-bonding inter-actions; one of the inter-actions results in dimers of the title mol-ecule lying about inversion centers in R(2) (2)(12) motifs and the other forms chains of mol-ecules lying along the c axis.

Related literature

For background to ferroelectric compounds, see: Haertling (1999 ▶); Homes et al. (2001 ▶). For related structures, see: Adolf et al. (1996 ▶); Kaida et al. (1990 ▶). For graph-set notation, see: Bernstein et al. (1994 ▶).

Experimental

Crystal data

C4H4N4O

M = 124.11

Monoclinic,

a = 6.5622 (13) Å

b = 8.9765 (18) Å

c = 11.008 (4) Å

β = 108.55 (3)°

V = 614.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.742, T max = 1.000

6154 measured reflections

1408 independent reflections

1094 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.162

S = 1.05

1408 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 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 datablocks I, global. DOI: 10.1107/S1600536810017265/pv2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017265/pv2279Isup2.hkl

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

C4H4N4O	F(000) = 256
Mr = 124.11	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1409 reflections
a = 6.5622 (13) Å	θ = 2.3–27.5°
b = 8.9765 (18) Å	µ = 0.10 mm−1
c = 11.008 (4) Å	T = 293 K
β = 108.55 (3)°	Prism, colorless
V = 614.7 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	1408 independent reflections
Radiation source: fine-focus sealed tube	1094 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.742, Tmax = 1.000	l = −14→14
6154 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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1408 reflections	Δρmax = 0.20 e Å−3
83 parameters	Δρmin = −0.20 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: 0.15 (2)

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
O1	0.1721 (2)	−0.00421 (14)	0.24979 (14)	0.0738 (5)
N1	0.1213 (3)	0.3227 (2)	0.03826 (14)	0.0730 (6)
N2	0.6354 (3)	0.36079 (17)	0.61699 (14)	0.0593 (5)
N3	0.3553 (2)	0.02971 (15)	0.31634 (14)	0.0537 (5)
N4	0.38510 (18)	0.17474 (12)	0.33544 (10)	0.0345 (4)
C2	0.6201 (2)	0.29919 (17)	0.52436 (14)	0.0411 (4)
C1	0.6039 (2)	0.22069 (18)	0.40327 (13)	0.0419 (4)
H1A	0.6543	0.2860	0.3487	0.050*
H1B	0.6962	0.1336	0.4222	0.050*
C4	0.1609 (2)	0.30241 (19)	0.14509 (15)	0.0439 (4)
C3	0.2111 (2)	0.28025 (16)	0.28328 (13)	0.0405 (4)
H3B	0.2504	0.3752	0.3264	0.049*
H3C	0.0835	0.2446	0.3006	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0564 (9)	0.0523 (9)	0.0991 (11)	−0.0192 (6)	0.0056 (7)	−0.0124 (6)
N1	0.0569 (11)	0.1157 (16)	0.0448 (9)	0.0196 (9)	0.0140 (7)	0.0171 (8)
N2	0.0655 (11)	0.0593 (10)	0.0484 (8)	−0.0107 (8)	0.0113 (7)	−0.0105 (7)
N3	0.0509 (9)	0.0336 (8)	0.0697 (10)	−0.0029 (6)	0.0094 (7)	−0.0008 (6)
N4	0.0342 (7)	0.0298 (7)	0.0356 (7)	0.0010 (5)	0.0056 (5)	0.0001 (4)
C2	0.0369 (8)	0.0392 (8)	0.0407 (8)	−0.0047 (6)	0.0032 (6)	0.0029 (6)
C1	0.0357 (9)	0.0485 (9)	0.0387 (8)	−0.0044 (7)	0.0076 (6)	−0.0030 (6)
C4	0.0339 (8)	0.0545 (9)	0.0390 (9)	0.0035 (7)	0.0058 (6)	0.0048 (6)
C3	0.0449 (9)	0.0372 (8)	0.0352 (8)	0.0099 (6)	0.0067 (6)	−0.0017 (6)

O1—N3	1.2305 (18)	C2—C1	1.481 (2)
N1—C4	1.135 (2)	C1—H1A	0.9700
N2—C2	1.136 (2)	C1—H1B	0.9700
N3—N4	1.3233 (18)	C4—C3	1.464 (2)
N4—C1	1.4516 (18)	C3—H3B	0.9700
N4—C3	1.4539 (17)	C3—H3C	0.9700
O1—N3—N4	113.89 (13)	C2—C1—H1B	109.2
N3—N4—C1	115.67 (12)	H1A—C1—H1B	107.9
N3—N4—C3	121.36 (12)	N1—C4—C3	178.53 (19)
C1—N4—C3	122.83 (12)	N4—C3—C4	112.80 (12)
N2—C2—C1	178.83 (17)	N4—C3—H3B	109.0
N4—C1—C2	111.97 (13)	C4—C3—H3B	109.0
N4—C1—H1A	109.2	N4—C3—H3C	109.0
C2—C1—H1A	109.2	C4—C3—H3C	109.0
N4—C1—H1B	109.2	H3B—C3—H3C	107.8

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···N2i	0.97	2.50	3.450 (2)	165
C3—H3C···N1ii	0.97	2.62	3.183 (2)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯N2i	0.97	2.50	3.450 (2)	165
C3—H3C⋯N1ii	0.97	2.62	3.183 (2)	117

Symmetry codes: (i) ; (ii) .