2-Amino-6-(dimethyl-amino)pyridine-3,5-dicarbonitrile.

The title compound, C(9)H(9)N(5), is slightly twisted from planarity, with a maximum deviation of 0.0285 (13) Å from the pyridine plane for the C atom bearing the amino group. The cyano groups are on different sides of the pyridine plane, with C- and N-atom deviations of 0.072 (3)/0.124 (4) and -0.228 (4)/-0.409 (5) Å from the pyridine plane. In the crystal, N-H⋯N and C-H⋯N hydrogen bonds connect the mol-ecules into zigzag chains running along the c axis.

Related literature

For the synthesis of similar structures, see: Horton et al. (2012a ▶,b ▶); Soliman et al. (2012 ▶). For the biological significance of cyano­amino pyridines, see: Al-Haiza et al. (2003 ▶); Bhalerao & Krishnaiah (1995 ▶); Deo et al. (1990 ▶); Murata et al. (2003 ▶); Konda et al. (2010 ▶); Altomare et al. (2000 ▶); Hosni & Abdulla (2008 ▶); Shishoo et al. (1983 ▶).

Experimental

Crystal data

C9H9N5

M = 187.21

Monoclinic,

a = 28.667 (7) Å

b = 3.9702 (10) Å

c = 17.950 (4) Å

β = 112.920 (3)°

V = 1881.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.21 × 0.03 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.972, T max = 0.997

4846 measured reflections

1658 independent reflections

1173 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.03

1658 reflections

138 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017278/im2369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017278/im2369Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017278/im2369Isup3.cml

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

C9H9N5	F(000) = 784
Mr = 187.21	Dx = 1.322 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4846 reflections
a = 28.667 (7) Å	θ = 3.1–25.0°
b = 3.9702 (10) Å	µ = 0.09 mm−1
c = 17.950 (4) Å	T = 296 K
β = 112.920 (3)°	Plate, yellow
V = 1881.7 (8) Å3	0.32 × 0.21 × 0.03 mm
Z = 8

Bruker SMART 1000 CCD diffractometer	1658 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −33→34
Tmin = 0.972, Tmax = 0.997	k = −4→4
4846 measured reflections	l = −21→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0915P)2 + 0.1839P] where P = (Fo2 + 2Fc2)/3
1658 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.07712 (6)	0.0877 (4)	0.27256 (9)	0.0417 (5)
N2	0.00997 (6)	0.2230 (6)	0.15638 (13)	0.0573 (6)
H1	−0.0050 (9)	0.284 (6)	0.1053 (17)	0.068 (8)*
H2	−0.0096 (12)	0.128 (8)	0.1777 (19)	0.094 (9)*
N3	0.05670 (8)	0.6406 (6)	0.02533 (12)	0.0669 (6)
N4	0.25896 (8)	0.0677 (9)	0.35083 (15)	0.1042 (10)
N5	0.14100 (6)	−0.0606 (5)	0.39210 (10)	0.0488 (5)
C1	0.06018 (7)	0.2187 (5)	0.19854 (12)	0.0415 (5)
C2	0.09339 (7)	0.3580 (5)	0.16489 (12)	0.0431 (5)
C3	0.14482 (7)	0.3269 (6)	0.20982 (13)	0.0499 (6)
H3	0.1676	0.4079	0.1887	0.060*
C4	0.16300 (7)	0.1796 (5)	0.28473 (13)	0.0463 (5)
C5	0.12699 (7)	0.0699 (5)	0.31732 (12)	0.0413 (5)
C6	0.07369 (8)	0.5132 (6)	0.08746 (14)	0.0498 (6)
C7	0.21622 (9)	0.1175 (7)	0.32283 (15)	0.0673 (7)
C8	0.18827 (9)	0.0208 (8)	0.45832 (15)	0.0782 (8)
H8A	0.1828	0.0356	0.5077	0.117*
H8B	0.2006	0.2328	0.4478	0.117*
H8C	0.2127	−0.1520	0.4634	0.117*
C9	0.10351 (8)	−0.2200 (6)	0.41700 (13)	0.0561 (6)
H9A	0.1197	−0.3882	0.4572	0.084*
H9B	0.0778	−0.3238	0.3710	0.084*
H9C	0.0884	−0.0530	0.4392	0.084*

	U11	U22	U33	U12	U13	U23
N1	0.0341 (9)	0.0539 (10)	0.0397 (10)	−0.0009 (7)	0.0172 (7)	−0.0014 (8)
N2	0.0344 (10)	0.0948 (16)	0.0427 (12)	−0.0056 (9)	0.0150 (9)	0.0117 (11)
N3	0.0644 (13)	0.0872 (15)	0.0559 (13)	−0.0010 (11)	0.0308 (11)	0.0131 (12)
N4	0.0412 (12)	0.175 (3)	0.0971 (19)	0.0216 (15)	0.0270 (12)	−0.0016 (19)
N5	0.0376 (9)	0.0639 (11)	0.0435 (10)	0.0045 (8)	0.0142 (8)	0.0037 (9)
C1	0.0364 (10)	0.0501 (12)	0.0411 (12)	−0.0021 (8)	0.0186 (9)	−0.0048 (9)
C2	0.0404 (11)	0.0522 (12)	0.0425 (12)	−0.0026 (9)	0.0224 (9)	−0.0020 (10)
C3	0.0419 (12)	0.0610 (13)	0.0572 (14)	−0.0054 (9)	0.0307 (11)	−0.0060 (11)
C4	0.0332 (11)	0.0580 (13)	0.0515 (13)	0.0009 (9)	0.0205 (9)	−0.0041 (11)
C5	0.0348 (10)	0.0455 (11)	0.0449 (12)	0.0010 (8)	0.0169 (9)	−0.0067 (9)
C6	0.0468 (12)	0.0611 (14)	0.0509 (14)	−0.0040 (10)	0.0292 (11)	−0.0023 (12)
C7	0.0445 (14)	0.0956 (19)	0.0682 (17)	0.0067 (12)	0.0288 (12)	−0.0019 (14)
C8	0.0492 (14)	0.108 (2)	0.0642 (17)	0.0041 (14)	0.0074 (12)	0.0105 (16)
C9	0.0532 (13)	0.0662 (14)	0.0575 (14)	0.0078 (11)	0.0310 (12)	0.0106 (12)

N1—C1	1.330 (2)	C2—C6	1.421 (3)
N1—C5	1.341 (2)	C3—C4	1.370 (3)
N2—C1	1.340 (3)	C3—H3	0.9300
N2—H1	0.88 (3)	C4—C7	1.429 (3)
N2—H2	0.88 (3)	C4—C5	1.438 (3)
N3—C6	1.146 (3)	C8—H8A	0.9600
N4—C7	1.146 (3)	C8—H8B	0.9600
N5—C5	1.346 (3)	C8—H8C	0.9600
N5—C8	1.449 (3)	C9—H9A	0.9600
N5—C9	1.459 (3)	C9—H9B	0.9600
C1—C2	1.423 (3)	C9—H9C	0.9600
C2—C3	1.383 (3)
C1—N1—C5	120.56 (16)	C7—C4—C5	123.7 (2)
C1—N2—H1	124.9 (15)	N1—C5—N5	116.88 (16)
C1—N2—H2	118 (2)	N1—C5—C4	120.45 (18)
H1—N2—H2	116 (3)	N5—C5—C4	122.66 (18)
C5—N5—C8	123.56 (19)	N3—C6—C2	178.3 (2)
C5—N5—C9	120.21 (17)	N4—C7—C4	177.7 (3)
C8—N5—C9	114.24 (18)	N5—C8—H8A	109.5
N1—C1—N2	117.60 (18)	N5—C8—H8B	109.5
N1—C1—C2	122.11 (18)	H8A—C8—H8B	109.5
N2—C1—C2	120.28 (19)	N5—C8—H8C	109.5
C3—C2—C6	122.45 (17)	H8A—C8—H8C	109.5
C3—C2—C1	117.08 (19)	H8B—C8—H8C	109.5
C6—C2—C1	120.45 (17)	N5—C9—H9A	109.5
C4—C3—C2	121.48 (18)	N5—C9—H9B	109.5
C4—C3—H3	119.3	H9A—C9—H9B	109.5
C2—C3—H3	119.3	N5—C9—H9C	109.5
C3—C4—C7	118.05 (19)	H9A—C9—H9C	109.5
C3—C4—C5	118.02 (18)	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3i	0.88 (3)	2.25 (3)	3.119 (3)	167 (2)
N2—H2···N1ii	0.88 (3)	2.43 (3)	3.260 (3)	158 (3)
C3—H3···N4iii	0.93	2.55	3.471 (4)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N3i	0.88 (3)	2.25 (3)	3.119 (3)	167 (2)
N2—H2⋯N1ii	0.88 (3)	2.43 (3)	3.260 (3)	158 (3)
C3—H3⋯N4iii	0.93	2.55	3.471 (4)	170

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