3,4-Diamino-benzonitrile.

The non-H atoms in the structure of the title mol-ecule, C7H7N3, are almost coplanar (r.m.s. deviation = 0.018 Å). The two amine groups each donate two and accept one weak N-H⋯N hydrogen bonds. N-H⋯N hydrogen bonding between the amine and nitrile groups results in chains parallel to [101] in the crystal structure. The chains are cross-linked by N-H⋯N hydrogen bonds between amine groups, giving rise to an infinite three-dimensional network.

Related literature

For the crystal structures of related compounds, see: Czapik & Gdaniec (2010 ▶); Stålhandske (1981 ▶).

Experimental

Crystal data

C7H7N3

M = 133.16

Monoclinic,

a = 8.858 (3) Å

b = 10.536 (4) Å

c = 8.160 (3) Å

β = 116.213 (12)°

V = 683.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.50 × 0.20 × 0.10 mm

Data collection

Bruker SMART X2S CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.85, T max = 0.99

2149 measured reflections

1188 independent reflections

662 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.128

S = 0.96

1188 reflections

107 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2010 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005151/qk2053sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005151/qk2053Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005151/qk2053Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005151/qk2053Isup4.cml

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

C7H7N3	F(000) = 280
Mr = 133.16	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 516 reflections
a = 8.858 (3) Å	θ = 2.6–21.2°
b = 10.536 (4) Å	µ = 0.08 mm−1
c = 8.160 (3) Å	T = 200 K
β = 116.213 (12)°	Prism, colourless
V = 683.2 (4) Å3	0.50 × 0.20 × 0.10 mm
Z = 4

Bruker SMART X2S CCD diffractometer	1188 independent reflections
Radiation source: fine-focus sealed tube	662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm-1	θmax = 25.2°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2010)	k = −12→11
Tmin = 0.85, Tmax = 0.99	l = −5→9
2149 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3
1188 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. 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.

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	1.0289 (3)	0.4587 (3)	0.7729 (3)	0.0317 (7)
H1A	1.025 (3)	0.538 (3)	0.809 (4)	0.053 (10)*
H1B	1.135 (4)	0.433 (3)	0.798 (4)	0.063 (11)*
N3	0.3764 (3)	0.3161 (2)	−0.0415 (3)	0.0495 (8)
N2	1.0370 (3)	0.2330 (2)	0.5881 (3)	0.0327 (7)
H2A	1.044 (3)	0.180 (3)	0.507 (4)	0.035 (8)*
H2B	1.142 (4)	0.264 (3)	0.670 (4)	0.068 (11)*
C1	0.8972 (3)	0.4302 (2)	0.6030 (3)	0.0259 (7)
C2	0.9008 (3)	0.3168 (2)	0.5098 (3)	0.0253 (7)
C3	0.7650 (3)	0.2879 (2)	0.3464 (3)	0.0276 (7)
H3	0.7664	0.2122	0.2838	0.033*
C4	0.6251 (3)	0.3686 (3)	0.2712 (3)	0.0298 (7)
C7	0.4877 (3)	0.3387 (3)	0.0985 (4)	0.0366 (8)
C5	0.6212 (3)	0.4783 (3)	0.3641 (3)	0.0323 (8)
H5	0.5262	0.5329	0.3150	0.039*
C6	0.7562 (3)	0.5071 (3)	0.5275 (3)	0.0305 (7)
H6	0.7525	0.5820	0.5905	0.037*

	U11	U22	U33	U12	U13	U23
N1	0.0325 (16)	0.0300 (17)	0.0274 (13)	−0.0019 (12)	0.0086 (13)	−0.0039 (12)
N3	0.0410 (15)	0.0481 (18)	0.0418 (15)	−0.0042 (13)	0.0022 (14)	0.0047 (13)
N2	0.0311 (14)	0.0309 (15)	0.0300 (13)	0.0049 (12)	0.0080 (12)	−0.0032 (12)
C1	0.0271 (15)	0.0256 (16)	0.0251 (14)	−0.0025 (12)	0.0115 (13)	0.0030 (12)
C2	0.0233 (14)	0.0259 (16)	0.0268 (14)	−0.0006 (12)	0.0111 (13)	0.0047 (13)
C3	0.0278 (14)	0.0264 (17)	0.0258 (14)	−0.0028 (12)	0.0092 (13)	0.0008 (12)
C4	0.0237 (14)	0.0338 (18)	0.0277 (15)	−0.0037 (13)	0.0074 (13)	0.0011 (13)
C7	0.0305 (16)	0.036 (2)	0.0387 (17)	0.0015 (13)	0.0108 (16)	0.0062 (14)
C5	0.0272 (15)	0.0324 (19)	0.0366 (16)	0.0020 (13)	0.0134 (14)	0.0036 (13)
C6	0.0345 (16)	0.0252 (16)	0.0327 (16)	0.0016 (13)	0.0156 (14)	−0.0015 (12)

N1—C1	1.395 (3)	C2—C3	1.379 (3)
N1—H1A	0.89 (3)	C3—C4	1.401 (3)
N1—H1B	0.91 (3)	C3—H3	0.9500
N3—C7	1.157 (3)	C4—C5	1.392 (4)
N2—C2	1.401 (3)	C4—C7	1.432 (3)
N2—H2A	0.90 (3)	C5—C6	1.375 (3)
N2—H2B	0.93 (3)	C5—H5	0.9500
C1—C6	1.384 (3)	C6—H6	0.9500
C1—C2	1.424 (3)
C1—N1—H1A	113.1 (17)	C2—C3—H3	119.5
C1—N1—H1B	119 (2)	C4—C3—H3	119.5
H1A—N1—H1B	113 (3)	C5—C4—C3	119.7 (2)
C2—N2—H2A	112.9 (16)	C5—C4—C7	120.2 (2)
C2—N2—H2B	119 (2)	C3—C4—C7	120.0 (2)
H2A—N2—H2B	112 (2)	N3—C7—C4	179.2 (3)
C6—C1—N1	120.7 (3)	C6—C5—C4	119.4 (2)
C6—C1—C2	118.8 (2)	C6—C5—H5	120.3
N1—C1—C2	120.4 (2)	C4—C5—H5	120.3
C3—C2—N2	120.6 (2)	C5—C6—C1	122.0 (3)
C3—C2—C1	119.1 (2)	C5—C6—H6	119.0
N2—C2—C1	120.2 (2)	C1—C6—H6	119.0
C2—C3—C4	121.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.89 (3)	2.37 (3)	3.251 (4)	168 (3)
N1—H1B···N3ii	0.91 (3)	2.31 (3)	3.147 (4)	154 (3)
N2—H2A···N1iii	0.90 (3)	2.36 (3)	3.246 (4)	173 (2)
N2—H2B···N3ii	0.93 (3)	2.42 (3)	3.303 (4)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.89 (3)	2.37 (3)	3.251 (4)	168 (3)
N1—H1B⋯N3ii	0.91 (3)	2.31 (3)	3.147 (4)	154 (3)
N2—H2A⋯N1iii	0.90 (3)	2.36 (3)	3.246 (4)	173 (2)
N2—H2B⋯N3ii	0.93 (3)	2.42 (3)	3.303 (4)	159 (3)

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