(E)-2-Acetyl-pyrazine 4-nitro-phenyl-hydrazone.

In the title compound, C(12)H(11)N(5)O(2), the mol-ecule adopts an E configuration, with the benzene and pyrazine rings located on opposite sides of the N=C double bond. The face-to-face separations of 3.413 (14) and 3.430 (8) Å, respectively between parallel benzene rings and between pyrazine rings indicate the existence of π-π stacking between adjacent mol-ecules. The crystal structure also contains N-H⋯N and C-H⋯O hydrogen bonding.

Related literature

For general background, see: Okabe et al. (1993 ▶); Hu et al. (2001 ▶); Chen et al. (2007 ▶). For a related structure, see: Shan et al. (2008 ▶).

Experimental

Crystal data

C12H11N5O2

M = 257.26

Monoclinic,

a = 8.0101 (6) Å

b = 12.5154 (11) Å

c = 12.1506 (12) Å

β = 98.564 (2)°

V = 1204.51 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.40 × 0.38 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

11633 measured reflections

2747 independent reflections

1446 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.149

S = 1.08

2747 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017479/sg2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017479/sg2248Isup2.hkl

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

C12H11N5O2	F000 = 536
Mr = 257.26	Dx = 1.419 Mg m−3
Monoclinic, P21/n	Melting point: 498 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71069 Å
a = 8.0101 (6) Å	Cell parameters from 4236 reflections
b = 12.5154 (11) Å	θ = 3.2–25.0º
c = 12.1506 (12) Å	µ = 0.10 mm−1
β = 98.564 (2)º	T = 295 (2) K
V = 1204.51 (18) Å3	Prism, yellow
Z = 4	0.40 × 0.38 × 0.26 mm

Rigaku R-AXIS RAPID IP diffractometer	2747 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 10.00 pixels mm-1	θmax = 27.4º
T = 295(2) K	θmin = 3.0º
ω scans	h = −10→10
Absorption correction: none	k = −16→16
11633 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.2787P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.20 e Å−3
2747 reflections	Δρmin = −0.19 e Å−3
174 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)
Secondary atom site location: difference Fourier map

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	0.9003 (3)	0.68785 (16)	0.3418 (2)	0.0684 (6)
N2	0.6332 (2)	0.36085 (12)	0.57394 (13)	0.0448 (4)
H2N	0.6470	0.3652	0.6496	0.054*
N3	0.5365 (2)	0.28334 (12)	0.51838 (13)	0.0425 (4)
N4	0.3197 (2)	0.04376 (14)	0.55830 (14)	0.0518 (5)
N5	0.2175 (2)	0.07812 (15)	0.33069 (14)	0.0571 (5)
O1	0.9806 (3)	0.75846 (16)	0.3955 (2)	0.1041 (8)
O2	0.8729 (3)	0.68826 (16)	0.2397 (2)	0.1012 (8)
C1	0.6976 (2)	0.43994 (15)	0.51344 (16)	0.0412 (5)
C2	0.7855 (3)	0.52394 (16)	0.57162 (17)	0.0490 (5)
H2	0.7989	0.5251	0.6490	0.059*
C3	0.8519 (3)	0.60439 (16)	0.51558 (18)	0.0521 (5)
H3	0.9109	0.6601	0.5544	0.062*
C4	0.8306 (3)	0.60198 (15)	0.40117 (18)	0.0488 (5)
C5	0.7461 (3)	0.51920 (17)	0.34168 (17)	0.0513 (5)
H5	0.7339	0.5187	0.2644	0.062*
C6	0.6803 (3)	0.43744 (17)	0.39758 (16)	0.0482 (5)
H6	0.6246	0.3809	0.3583	0.058*
C7	0.4778 (2)	0.20837 (14)	0.57459 (15)	0.0408 (5)
C8	0.5120 (3)	0.19727 (18)	0.69835 (17)	0.0593 (6)
H8A	0.6317	0.1939	0.7222	0.089*
H8B	0.4602	0.1331	0.7202	0.089*
H8C	0.4663	0.2578	0.7322	0.089*
C9	0.3700 (2)	0.13023 (15)	0.50718 (15)	0.0408 (5)
C10	0.3179 (3)	0.14575 (16)	0.39353 (16)	0.0496 (5)
H10	0.3553	0.2063	0.3602	0.059*
C11	0.1699 (3)	−0.00860 (18)	0.38283 (19)	0.0569 (6)
H11	0.1002	−0.0587	0.3424	0.068*
C12	0.2214 (3)	−0.02519 (17)	0.49398 (19)	0.0554 (6)
H12	0.1865	−0.0871	0.5263	0.067*

	U11	U22	U33	U12	U13	U23
N1	0.0742 (15)	0.0486 (11)	0.0895 (17)	0.0037 (10)	0.0352 (12)	0.0135 (11)
N2	0.0566 (11)	0.0430 (9)	0.0341 (8)	−0.0036 (8)	0.0039 (7)	−0.0005 (7)
N3	0.0478 (10)	0.0391 (8)	0.0397 (9)	0.0001 (7)	0.0036 (7)	−0.0009 (7)
N4	0.0623 (12)	0.0469 (10)	0.0465 (10)	−0.0033 (8)	0.0094 (8)	0.0044 (8)
N5	0.0678 (13)	0.0578 (11)	0.0435 (10)	−0.0075 (9)	0.0012 (9)	−0.0042 (9)
O1	0.1140 (18)	0.0645 (12)	0.137 (2)	−0.0350 (12)	0.0270 (15)	0.0119 (13)
O2	0.146 (2)	0.0841 (14)	0.0860 (15)	−0.0086 (13)	0.0569 (14)	0.0232 (12)
C1	0.0454 (11)	0.0388 (10)	0.0393 (10)	0.0033 (8)	0.0064 (8)	−0.0002 (8)
C2	0.0588 (13)	0.0456 (11)	0.0419 (11)	−0.0015 (10)	0.0050 (9)	−0.0038 (9)
C3	0.0542 (13)	0.0412 (11)	0.0609 (14)	−0.0029 (9)	0.0087 (10)	−0.0062 (10)
C4	0.0517 (12)	0.0405 (10)	0.0577 (13)	0.0055 (9)	0.0198 (10)	0.0075 (10)
C5	0.0610 (14)	0.0527 (12)	0.0414 (11)	0.0029 (10)	0.0117 (10)	0.0022 (10)
C6	0.0569 (13)	0.0471 (11)	0.0411 (11)	−0.0013 (10)	0.0088 (9)	−0.0023 (9)
C7	0.0469 (12)	0.0381 (10)	0.0370 (10)	0.0050 (8)	0.0046 (8)	0.0027 (8)
C8	0.0780 (17)	0.0573 (13)	0.0396 (12)	−0.0086 (12)	−0.0009 (11)	0.0065 (10)
C9	0.0459 (11)	0.0391 (10)	0.0379 (10)	0.0036 (8)	0.0079 (8)	0.0035 (8)
C10	0.0605 (14)	0.0483 (11)	0.0394 (11)	−0.0045 (10)	0.0060 (10)	0.0024 (9)
C11	0.0619 (15)	0.0520 (13)	0.0561 (13)	−0.0091 (11)	0.0064 (11)	−0.0063 (11)
C12	0.0634 (14)	0.0473 (12)	0.0568 (13)	−0.0107 (10)	0.0127 (11)	0.0019 (11)

N1—O1	1.223 (3)	C3—H3	0.9300
N1—O2	1.226 (3)	C4—C5	1.381 (3)
N1—C4	1.452 (3)	C5—C6	1.376 (3)
N2—N3	1.357 (2)	C5—H5	0.9300
N2—C1	1.378 (2)	C6—H6	0.9300
N2—H2N	0.9106	C7—C9	1.470 (3)
N3—C7	1.290 (2)	C7—C8	1.494 (3)
N4—C12	1.339 (3)	C8—H8A	0.9600
N4—C9	1.339 (2)	C8—H8B	0.9600
N5—C10	1.328 (3)	C8—H8C	0.9600
N5—C11	1.340 (3)	C9—C10	1.395 (3)
C1—C6	1.394 (3)	C10—H10	0.9300
C1—C2	1.397 (3)	C11—C12	1.368 (3)
C2—C3	1.367 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.375 (3)
O1—N1—O2	122.5 (2)	C5—C6—C1	119.6 (2)
O1—N1—C4	118.7 (2)	C5—C6—H6	120.2
O2—N1—C4	118.8 (2)	C1—C6—H6	120.2
N3—N2—C1	118.65 (15)	N3—C7—C9	114.78 (16)
N3—N2—H2N	121.3	N3—C7—C8	125.00 (18)
C1—N2—H2N	119.8	C9—C7—C8	120.23 (17)
C7—N3—N2	118.88 (16)	C7—C8—H8A	109.5
C12—N4—C9	116.19 (18)	C7—C8—H8B	109.5
C10—N5—C11	115.78 (18)	H8A—C8—H8B	109.5
N2—C1—C6	122.25 (18)	C7—C8—H8C	109.5
N2—C1—C2	118.10 (17)	H8A—C8—H8C	109.5
C6—C1—C2	119.64 (19)	H8B—C8—H8C	109.5
C3—C2—C1	120.42 (19)	N4—C9—C10	120.35 (18)
C3—C2—H2	119.8	N4—C9—C7	118.11 (16)
C1—C2—H2	119.8	C10—C9—C7	121.53 (17)
C2—C3—C4	119.2 (2)	N5—C10—C9	123.13 (19)
C2—C3—H3	120.4	N5—C10—H10	118.4
C4—C3—H3	120.4	C9—C10—H10	118.4
C3—C4—C5	121.53 (19)	N5—C11—C12	121.6 (2)
C3—C4—N1	119.1 (2)	N5—C11—H11	119.2
C5—C4—N1	119.3 (2)	C12—C11—H11	119.2
C6—C5—C4	119.56 (19)	N4—C12—C11	122.9 (2)
C6—C5—H5	120.2	N4—C12—H12	118.6
C4—C5—H5	120.2	C11—C12—H12	118.6

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N5i	0.91	2.30	3.185 (2)	164
C11—H11···O1ii	0.93	2.60	3.300 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N5i	0.91	2.30	3.185 (2)	164
C11—H11⋯O1ii	0.93	2.60	3.300 (3)	133

Symmetry codes: (i) ; (ii) .