[1-(Pyrazin-2-yl)ethyl­idene]hydrazine: a new multitopic ligand for the design of hybrid mol­ecular frameworks

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, C₆H₈N₄, 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.

Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.42 × 0.41 × 0.26 mm

Data collection

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

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.265P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.054 (6)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1X···N3^i	0.910 (19)	2.404 (19)	3.2440 (14)	153.5 (15)
N1—H1Y···N4^ii	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.