Hydrazones and their derivatives are closely related to imine compounds and are potential antimicrobial agents. They have also found application in supramolecular chemistry as multitopic ligands to link multiple metal centres for the design of hybrid molecular frameworks. The molecule of the title compound, C
6H
8N
4, consists of an imine linkage with an N—N bond length of 1.3540 (14) Å. This asymmetric compound is nearly planar and adopts an
E configuration about the azomethine C=N double bond. In the solid state, there are two intermolecular N—H

N interactions that interconnect the molecules into a two-dimensional network. The three-dimensional arrangement of the crystal packing is further stabilized by intermolecular π–π interactions interconnecting the centroids of the heterocyclic rings.
Supporting information
CCDC reference: 1576941
Data collection: SAINT (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2008) and WinGX (Farrugia, 2012).
[1-(Pyrazin-2-yl)ethylidene]hydrazine
top
Crystal data top
C6H8N4 | F(000) = 288 |
Mr = 136.16 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 6.9312 (2) Å | Cell parameters from 4009 reflections |
b = 14.6542 (5) Å | θ = 6.8–74.3° |
c = 7.1239 (3) Å | µ = 0.75 mm−1 |
β = 114.011 (1)° | T = 100 K |
V = 660.97 (4) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.41 × 0.26 mm |
Data collection top
Bruker D8 Venture diffractometer | 1214 reflections with I > 2σ(I) |
Radiation source: Sealed Microfocus Source | Rint = 0.025 |
φ and ω scans | θmax = 70.0°, θmin = 6.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→8 |
Tmin = 0.637, Tmax = 0.754 | k = −17→17 |
4097 measured reflections | l = −8→4 |
1229 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.265P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.28 e Å−3 |
1229 reflections | Δρmin = −0.20 e Å−3 |
101 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.054 (6) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.76455 (16) | 0.47652 (7) | 0.81644 (16) | 0.0191 (3) | |
H1X | 0.886 (3) | 0.4583 (12) | 0.808 (3) | 0.036 (4)* | |
H1Y | 0.721 (3) | 0.5357 (13) | 0.791 (3) | 0.030 (4)* | |
N2 | 0.62317 (15) | 0.40754 (6) | 0.77471 (15) | 0.0154 (3) | |
N3 | 0.08891 (15) | 0.36195 (7) | 0.68272 (15) | 0.0161 (3) | |
N4 | 0.24593 (15) | 0.18410 (7) | 0.70304 (15) | 0.0176 (3) | |
C1 | 0.34168 (19) | 0.52187 (8) | 0.71706 (18) | 0.0174 (3) | |
H1A | 0.3859 | 0.5577 | 0.6253 | 0.026* | |
H1B | 0.3955 | 0.5505 | 0.8531 | 0.026* | |
H1C | 0.1871 | 0.5194 | 0.6607 | 0.026* | |
C2 | 0.42823 (18) | 0.42691 (7) | 0.73552 (17) | 0.0136 (3) | |
C3 | 0.29024 (17) | 0.34708 (7) | 0.71175 (16) | 0.0132 (3) | |
C4 | 0.36586 (18) | 0.25698 (8) | 0.72217 (18) | 0.0159 (3) | |
H4 | 0.5092 | 0.2481 | 0.7439 | 0.019* | |
C5 | 0.04403 (19) | 0.20021 (8) | 0.67168 (18) | 0.0181 (3) | |
H5 | −0.0483 | 0.1501 | 0.6557 | 0.022* | |
C6 | −0.03181 (19) | 0.28785 (8) | 0.66219 (19) | 0.0181 (3) | |
H6 | −0.1754 | 0.2961 | 0.6402 | 0.022* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0154 (5) | 0.0123 (6) | 0.0294 (6) | −0.0014 (4) | 0.0087 (4) | −0.0010 (4) |
N2 | 0.0159 (5) | 0.0122 (5) | 0.0177 (5) | −0.0015 (4) | 0.0065 (4) | −0.0010 (4) |
N3 | 0.0156 (5) | 0.0153 (5) | 0.0172 (5) | 0.0005 (4) | 0.0065 (4) | −0.0017 (4) |
N4 | 0.0194 (5) | 0.0142 (5) | 0.0191 (5) | −0.0004 (4) | 0.0077 (4) | −0.0005 (4) |
C1 | 0.0183 (6) | 0.0122 (6) | 0.0205 (6) | 0.0011 (4) | 0.0066 (5) | −0.0001 (4) |
C2 | 0.0156 (6) | 0.0133 (6) | 0.0116 (5) | 0.0014 (4) | 0.0052 (4) | 0.0000 (4) |
C3 | 0.0148 (6) | 0.0145 (6) | 0.0098 (5) | 0.0010 (4) | 0.0047 (4) | −0.0008 (4) |
C4 | 0.0154 (6) | 0.0145 (6) | 0.0177 (6) | 0.0007 (4) | 0.0066 (5) | 0.0001 (4) |
C5 | 0.0193 (6) | 0.0161 (6) | 0.0196 (6) | −0.0040 (5) | 0.0086 (5) | −0.0026 (5) |
C6 | 0.0150 (6) | 0.0198 (7) | 0.0199 (6) | −0.0016 (4) | 0.0074 (5) | −0.0030 (5) |
Geometric parameters (Å, º) top
N1—N2 | 1.3540 (14) | C1—H1A | 0.9800 |
N1—H1X | 0.910 (19) | C1—H1B | 0.9800 |
N1—H1Y | 0.912 (19) | C1—H1C | 0.9800 |
N2—C2 | 1.2950 (15) | C2—C3 | 1.4765 (15) |
N3—C6 | 1.3420 (15) | C3—C4 | 1.4114 (16) |
N3—C3 | 1.3426 (15) | C4—H4 | 0.9500 |
N4—C4 | 1.3259 (16) | C5—C6 | 1.3790 (17) |
N4—C5 | 1.3452 (15) | C5—H5 | 0.9500 |
C1—C2 | 1.4999 (15) | C6—H6 | 0.9500 |
| | | |
N2—N1—H1X | 111.9 (12) | C3—C2—C1 | 120.51 (10) |
N2—N1—H1Y | 121.0 (11) | N3—C3—C4 | 120.02 (10) |
H1X—N1—H1Y | 120.3 (16) | N3—C3—C2 | 118.25 (10) |
C2—N2—N1 | 118.83 (10) | C4—C3—C2 | 121.72 (10) |
C6—N3—C3 | 116.64 (10) | N4—C4—C3 | 122.97 (10) |
C4—N4—C5 | 116.24 (10) | N4—C4—H4 | 118.5 |
C2—C1—H1A | 109.5 | C3—C4—H4 | 118.5 |
C2—C1—H1B | 109.5 | N4—C5—C6 | 121.44 (11) |
H1A—C1—H1B | 109.5 | N4—C5—H5 | 119.3 |
C2—C1—H1C | 109.5 | C6—C5—H5 | 119.3 |
H1A—C1—H1C | 109.5 | N3—C6—C5 | 122.68 (11) |
H1B—C1—H1C | 109.5 | N3—C6—H6 | 118.7 |
N2—C2—C3 | 114.93 (10) | C5—C6—H6 | 118.7 |
N2—C2—C1 | 124.56 (10) | | |
| | | |
N1—N2—C2—C3 | −174.34 (9) | C1—C2—C3—C4 | 178.05 (10) |
N1—N2—C2—C1 | 4.82 (17) | C5—N4—C4—C3 | 0.27 (17) |
C6—N3—C3—C4 | −0.86 (16) | N3—C3—C4—N4 | 0.48 (18) |
C6—N3—C3—C2 | −179.85 (9) | C2—C3—C4—N4 | 179.43 (10) |
N2—C2—C3—N3 | 176.22 (9) | C4—N4—C5—C6 | −0.60 (17) |
C1—C2—C3—N3 | −2.98 (16) | C3—N3—C6—C5 | 0.55 (17) |
N2—C2—C3—C4 | −2.75 (16) | N4—C5—C6—N3 | 0.20 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1X···N3i | 0.910 (19) | 2.404 (19) | 3.2440 (14) | 153.5 (15) |
N1—H1Y···N4ii | 0.912 (19) | 2.185 (19) | 3.0446 (15) | 156.8 (15) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+3/2. |