2,2'-Sulfonyl-dipyrazine 4-oxide.

In the title compound, C(8)H(6)N(4)O(3)S, the dihedral angle between the pyrazine rings is 85.04 (1)°. In the crystal, mol-ecules are arranged along the a axis and are linked by C-H⋯N hydrogen bonds and pyrazine-pyrazine π-π inter-actions [centroid-centroid distance = 3.800 (1) Å, forming an infinite chain array. The chains are connected by C-H⋯O(oxide) hydrogen bonds into layers lying parallel to the ab plane. Along the c axis, the layers are stacked and linked through C-H⋯O(sulfon-yl) inter-actions, forming a three-dimensional network.

Related literature

For metal complexes with 2,2′-sulfonyl­dipyrazine, see: Wan & Mak (2011 ▶). For crystal structures of pyridyl-based N-oxide and their metal complexes, see: Jia et al. (2008 ▶).

Experimental

Crystal data

C8H6N4O3S

M = 238.23

Monoclinic,

a = 7.6860 (16) Å

b = 15.841 (3) Å

c = 9.0624 (14) Å

β = 117.813 (13)°

V = 975.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.45 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.688, T max = 1.000

6606 measured reflections

2429 independent reflections

1586 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.203

S = 1.07

2429 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028607/zq2171sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028607/zq2171Isup2.hkl

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

C8H6N4O3S	F(000) = 488
Mr = 238.23	Dx = 1.621 Mg m−3Dm = 1.621 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 365 reflections
a = 7.6860 (16) Å	θ = 2.6–28.4°
b = 15.841 (3) Å	µ = 0.33 mm−1
c = 9.0624 (14) Å	T = 296 K
β = 117.813 (13)°	Needle-like, colourless
V = 975.9 (3) Å3	0.45 × 0.30 × 0.25 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2429 independent reflections
Radiation source: fine-focus sealed tube	1586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.688, Tmax = 1.000	k = −21→11
6606 measured reflections	l = −12→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0981P)2 + 0.5688P] where P = (Fo2 + 2Fc2)/3
2429 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

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.

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 > 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.

	x	y	z	Uiso*/Ueq
S1	0.50844 (11)	0.33579 (5)	0.25247 (12)	0.0436 (3)
N1	0.8484 (4)	0.27476 (19)	0.2912 (4)	0.0531 (8)
N2	0.8080 (4)	0.12101 (18)	0.4199 (4)	0.0520 (8)
N3	0.6907 (4)	0.4321 (2)	0.5196 (4)	0.0540 (8)
N4	0.7631 (6)	0.5635 (2)	0.3499 (6)	0.0699 (10)
O1	0.4354 (3)	0.35188 (18)	0.0788 (3)	0.0581 (7)
O2	0.3755 (4)	0.31172 (17)	0.3141 (4)	0.0627 (8)
O3	0.7852 (6)	0.0494 (2)	0.4742 (6)	0.0996 (13)
C1	0.6949 (4)	0.25624 (19)	0.3152 (4)	0.0403 (7)
C2	0.6667 (5)	0.1820 (2)	0.3776 (5)	0.0494 (9)
H2A	0.5552	0.1732	0.3910	0.059*
C3	0.9681 (5)	0.1382 (2)	0.4026 (5)	0.0535 (9)
H3A	1.0685	0.0985	0.4351	0.064*
C4	0.9844 (5)	0.2134 (2)	0.3375 (6)	0.0582 (10)
H4A	1.0959	0.2229	0.3244	0.070*
C5	0.6391 (4)	0.4281 (2)	0.3598 (4)	0.0416 (8)
C6	0.7790 (6)	0.5037 (3)	0.5944 (6)	0.0627 (11)
H6A	0.8189	0.5105	0.7076	0.075*
C7	0.8125 (6)	0.5678 (3)	0.5086 (7)	0.0677 (13)
H7A	0.8734	0.6167	0.5664	0.081*
C8	0.6737 (5)	0.4914 (2)	0.2717 (5)	0.0561 (9)
H8A	0.6355	0.4843	0.1588	0.067*

	U11	U22	U33	U12	U13	U23
S1	0.0286 (4)	0.0384 (4)	0.0661 (6)	−0.0005 (3)	0.0238 (4)	−0.0064 (4)
N1	0.0336 (13)	0.0392 (15)	0.090 (2)	−0.0016 (11)	0.0314 (14)	0.0025 (14)
N2	0.0566 (17)	0.0332 (14)	0.073 (2)	0.0047 (13)	0.0357 (16)	0.0039 (14)
N3	0.0531 (17)	0.0451 (17)	0.062 (2)	0.0018 (13)	0.0250 (15)	−0.0052 (14)
N4	0.069 (2)	0.0405 (17)	0.110 (3)	−0.0067 (16)	0.050 (2)	−0.0055 (19)
O1	0.0378 (12)	0.0647 (17)	0.0632 (17)	0.0072 (11)	0.0165 (11)	−0.0084 (13)
O2	0.0493 (14)	0.0492 (15)	0.109 (2)	−0.0070 (12)	0.0529 (15)	−0.0115 (14)
O3	0.117 (3)	0.0558 (19)	0.159 (4)	0.020 (2)	0.092 (3)	0.033 (2)
C1	0.0313 (14)	0.0330 (15)	0.0563 (19)	−0.0009 (12)	0.0203 (13)	−0.0058 (14)
C2	0.0477 (18)	0.0394 (17)	0.074 (2)	0.0008 (14)	0.0395 (18)	−0.0013 (16)
C3	0.0350 (16)	0.0456 (19)	0.072 (2)	0.0044 (14)	0.0187 (16)	−0.0014 (18)
C4	0.0315 (16)	0.0463 (19)	0.099 (3)	0.0001 (14)	0.0318 (18)	0.0007 (19)
C5	0.0311 (14)	0.0333 (15)	0.062 (2)	0.0036 (12)	0.0230 (14)	−0.0017 (14)
C6	0.055 (2)	0.056 (2)	0.068 (3)	0.0036 (18)	0.0203 (19)	−0.017 (2)
C7	0.047 (2)	0.041 (2)	0.115 (4)	−0.0084 (16)	0.038 (2)	−0.024 (2)
C8	0.055 (2)	0.045 (2)	0.072 (3)	0.0007 (16)	0.0323 (19)	−0.0001 (18)

S1—O1	1.425 (3)	N4—C8	1.351 (5)
S1—O2	1.426 (3)	C1—C2	1.366 (5)
S1—C5	1.784 (3)	C2—H2A	0.9300
S1—C1	1.790 (3)	C3—C4	1.362 (6)
N1—C1	1.328 (4)	C3—H3A	0.9300
N1—C4	1.343 (4)	C4—H4A	0.9300
N2—O3	1.281 (4)	C5—C8	1.382 (5)
N2—C3	1.339 (5)	C6—C7	1.374 (7)
N2—C2	1.368 (4)	C6—H6A	0.9300
N3—C5	1.312 (5)	C7—H7A	0.9300
N3—C6	1.333 (5)	C8—H8A	0.9300
N4—C7	1.306 (6)
O1—S1—O2	119.66 (17)	N2—C3—C4	120.2 (3)
O1—S1—C5	106.68 (17)	N2—C3—H3A	119.9
O2—S1—C5	109.23 (16)	C4—C3—H3A	119.9
O1—S1—C1	108.72 (16)	N1—C4—C3	123.6 (3)
O2—S1—C1	107.53 (17)	N1—C4—H4A	118.2
C5—S1—C1	103.92 (14)	C3—C4—H4A	118.2
C1—N1—C4	114.3 (3)	N3—C5—C8	124.2 (3)
O3—N2—C3	121.5 (3)	N3—C5—S1	116.4 (3)
O3—N2—C2	120.0 (3)	C8—C5—S1	119.4 (3)
C3—N2—C2	118.5 (3)	N3—C6—C7	121.7 (4)
C5—N3—C6	114.9 (4)	N3—C6—H6A	119.1
C7—N4—C8	115.9 (4)	C7—C6—H6A	119.1
N1—C1—C2	125.6 (3)	N4—C7—C6	123.4 (4)
N1—C1—S1	115.7 (2)	N4—C7—H7A	118.3
C2—C1—S1	118.6 (2)	C6—C7—H7A	118.3
C1—C2—N2	117.7 (3)	N4—C8—C5	119.8 (4)
C1—C2—H2A	121.1	N4—C8—H8A	120.1
N2—C2—H2A	121.1	C5—C8—H8A	120.1
C4—N1—C1—C2	−1.3 (5)	N2—C3—C4—N1	1.6 (7)
C4—N1—C1—S1	−179.2 (3)	C6—N3—C5—C8	1.0 (5)
O1—S1—C1—N1	59.3 (3)	C6—N3—C5—S1	−176.7 (3)
O2—S1—C1—N1	−169.8 (3)	O1—S1—C5—N3	169.1 (2)
C5—S1—C1—N1	−54.1 (3)	O2—S1—C5—N3	38.4 (3)
O1—S1—C1—C2	−118.8 (3)	C1—S1—C5—N3	−76.1 (3)
O2—S1—C1—C2	12.1 (3)	O1—S1—C5—C8	−8.7 (3)
C5—S1—C1—C2	127.8 (3)	O2—S1—C5—C8	−139.4 (3)
N1—C1—C2—N2	0.1 (6)	C1—S1—C5—C8	106.1 (3)
S1—C1—C2—N2	178.0 (3)	C5—N3—C6—C7	−0.1 (5)
O3—N2—C2—C1	−177.9 (4)	C8—N4—C7—C6	0.5 (6)
C3—N2—C2—C1	1.9 (5)	N3—C6—C7—N4	−0.6 (6)
O3—N2—C3—C4	177.1 (4)	C7—N4—C8—C5	0.3 (6)
C2—N2—C3—C4	−2.8 (6)	N3—C5—C8—N4	−1.1 (5)
C1—N1—C4—C3	0.4 (6)	S1—C5—C8—N4	176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.32	3.130 (5)	146
C3—H3A···O3ii	0.93	2.56	3.419 (4)	153
C7—H7A···N1iii	0.93	2.57	3.449 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.32	3.130 (5)	146
C3—H3A⋯O3ii	0.93	2.56	3.419 (4)	153
C7—H7A⋯N1iii	0.93	2.57	3.449 (3)	157

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