2-[(Dimethyl-amino)-methyl-idene]propane-dinitrile.

In the title moleclue, C6H7N3, the mean plane of the dimethyl-amino group [maximum deviation = 0.006 (2) Å] forms a dihedral angle of 7.95 (18)° with the mean plane of the propane-dinitrile fragment [maximum deviation = 0.008 (2) Å]. In the crystal, weak C-H⋯N hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For applications of enamines, see: Omran et al. (1997 ▶); Saleh et al. (1999 ▶). For related structures, see: Kant et al. (2012 ▶); Karlsen et al. (2002 ▶).

Experimental

Crystal data

C6H7N3

M = 121.15

Monoclinic,

a = 4.0368 (3) Å

b = 15.5642 (10) Å

c = 10.8500 (7) Å

β = 97.488 (6)°

V = 675.89 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.637, T max = 1.000

15029 measured reflections

1320 independent reflections

875 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.206

S = 1.05

1320 reflections

84 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004960/lh5587sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004960/lh5587Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004960/lh5587Isup3.cml

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

C6H7N3	F(000) = 256
Mr = 121.15	Dx = 1.191 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3950 reflections
a = 4.0368 (3) Å	θ = 3.8–29.2°
b = 15.5642 (10) Å	µ = 0.08 mm−1
c = 10.8500 (7) Å	T = 293 K
β = 97.488 (6)°	Block, colourless
V = 675.89 (8) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1320 independent reflections
Radiation source: fine-focus sealed tube	875 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.8°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −19→19
Tmin = 0.637, Tmax = 1.000	l = −13→13
15029 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1075P)2 + 0.0919P] where P = (Fo2 + 2Fc2)/3
1320 reflections	(Δ/σ)max = 0.001
84 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.3330 (6)	0.77364 (16)	0.7562 (2)	0.0501 (7)
C2	0.2937 (6)	0.69295 (15)	0.7036 (2)	0.0510 (7)
H2	0.1698	0.6914	0.6251	0.061*
N3	0.4033 (5)	0.61815 (13)	0.74689 (19)	0.0565 (6)
C4	0.3449 (7)	0.54179 (18)	0.6690 (3)	0.0752 (9)
H4A	0.2019	0.5562	0.5941	0.113*
H4B	0.2401	0.4983	0.7132	0.113*
H4C	0.5542	0.5206	0.6483	0.113*
C5	0.5891 (7)	0.6056 (2)	0.8695 (3)	0.0726 (9)
H5A	0.7939	0.6377	0.8759	0.109*
H5B	0.6386	0.5457	0.8821	0.109*
H5C	0.4577	0.6253	0.9316	0.109*
C6	0.5281 (6)	0.79802 (16)	0.8689 (2)	0.0568 (7)
C7	0.1665 (6)	0.84244 (17)	0.6873 (2)	0.0578 (7)
N8	0.6838 (6)	0.82284 (18)	0.9572 (2)	0.0805 (8)
N9	0.0355 (6)	0.89864 (16)	0.6341 (2)	0.0789 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0514 (13)	0.0581 (15)	0.0392 (13)	−0.0003 (11)	0.0003 (10)	0.0009 (11)
C2	0.0508 (13)	0.0622 (17)	0.0391 (13)	−0.0035 (11)	0.0017 (10)	0.0040 (11)
N3	0.0647 (13)	0.0565 (13)	0.0466 (13)	0.0020 (10)	0.0009 (10)	0.0064 (10)
C4	0.090 (2)	0.0557 (17)	0.077 (2)	−0.0048 (14)	0.0003 (16)	−0.0040 (15)
C5	0.0853 (19)	0.0757 (19)	0.0537 (18)	0.0151 (15)	−0.0032 (14)	0.0126 (15)
C6	0.0573 (15)	0.0640 (17)	0.0477 (15)	0.0020 (12)	0.0016 (12)	−0.0023 (13)
C7	0.0643 (16)	0.0599 (16)	0.0469 (16)	−0.0022 (13)	−0.0018 (12)	−0.0053 (13)
N8	0.0883 (17)	0.0896 (19)	0.0576 (16)	−0.0012 (14)	−0.0125 (13)	−0.0126 (14)
N9	0.0944 (18)	0.0635 (15)	0.0717 (18)	0.0074 (13)	−0.0155 (14)	0.0030 (14)

C1—C2	1.380 (3)	C4—H4B	0.9600
C1—C6	1.417 (3)	C4—H4C	0.9600
C1—C7	1.424 (3)	C5—H5A	0.9600
C2—N3	1.311 (3)	C5—H5B	0.9600
C2—H2	0.9300	C5—H5C	0.9600
N3—C5	1.453 (3)	C6—N8	1.143 (3)
N3—C4	1.460 (3)	C7—N9	1.139 (3)
C4—H4A	0.9600
C2—C1—C6	128.4 (2)	N3—C4—H4C	109.5
C2—C1—C7	116.5 (2)	H4A—C4—H4C	109.5
C6—C1—C7	115.0 (2)	H4B—C4—H4C	109.5
N3—C2—C1	130.2 (2)	N3—C5—H5A	109.5
N3—C2—H2	114.9	N3—C5—H5B	109.5
C1—C2—H2	114.9	H5A—C5—H5B	109.5
C2—N3—C5	123.9 (2)	N3—C5—H5C	109.5
C2—N3—C4	119.6 (2)	H5A—C5—H5C	109.5
C5—N3—C4	116.5 (2)	H5B—C5—H5C	109.5
N3—C4—H4A	109.5	N8—C6—C1	175.8 (3)
N3—C4—H4B	109.5	N9—C7—C1	178.6 (3)
H4A—C4—H4B	109.5
C6—C1—C2—N3	5.6 (4)	C1—C2—N3—C5	2.7 (4)
C7—C1—C2—N3	−176.8 (2)	C1—C2—N3—C4	−176.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N8i	0.93	2.51	3.399 (4)	161
C4—H4B···N9ii	0.96	2.62	3.569 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N8i	0.93	2.51	3.399 (4)	161
C4—H4B⋯N9ii	0.96	2.62	3.569 (4)	170

Symmetry codes: (i) ; (ii) .