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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2285
https://doi.org/10.1107/S1600536812028607

2,2′-Sulfonyl­di­pyrazine 4-oxide

Ai-Min Li,a Ya Zhang,a Zhi-Wei Wanga and Chong-Qing Wana*

aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
*Correspondence e-mail: wanchqing@yahoo.com.cn

(Received 4 June 2012; accepted 23 June 2012; online 30 June 2012)

In the title compound, C8H6N4O3S, the dihedral angle between the pyrazine rings is 85.04 (1)°. In the crystal, mol­ecules are arranged along the a axis and are linked by C—H⋯N hydrogen bonds and pyrazine–pyrazine π–π inter­actions [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(sulfon­yl) inter­actions, forming a three-dimensional network.

Related literature

For metal complexes with 2,2′-sulfonyl­dipyrazine, see: Wan & Mak (2011[Wan, C. Q. & Mak, T. C. W. (2011). New J. Chem. 35, 319-327.]). For crystal structures of pyridyl-based N-oxide and their metal complexes, see: Jia et al. (2008[Jia, J. H., Blake, A. J., Champness, N. R., Hubberstey, P., Wilson, C. & Schröder, M. (2008). Inorg. Chem. 47, 8652-8664.]).

[Scheme 1]

Experimental

Crystal data

  • C8H6N4O3S

  • Mr = 238.23

  • Monoclinic, P 21 /c

  • 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.688, Tmax = 1.000

  • 6606 measured reflections

  • 2429 independent reflections

  • 1586 reflections with I > 2σ(I)

  • Rint = 0.058
Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 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

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) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+2, -y, -z+1; (iii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028607/zq2171sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028607/zq2171Isup2.hkl

checkCIF report


Comment top

Pyridyl based sulfonyl derivatives were widely used in supramolecular assemblies of transition metal complexes (Wan & Mak, 2011). Pyridyl based N-oxide derivatives have also been demonstrated as versatile building blocks to construct supramolecular architectures of various metal complexes (Jia et al., 2008). In the present context, we report the structure of the title compound, a new N-oxide compound derived from 2,2'-sulfonyldipyrazine.

In the title compound, the value of the C1(sp2)—S1—C5(sp2) angle is 103.92 (1)° with two attached pyrazinyl rings exhibiting a dihedral angle of 85.04 (1)°, as shown in Fig. 1. The angular-shaped molecules are arranged along the a axis. As shown in Fig. 2, two adjacent molecules arranged with an inversion center are interconnected through C7—H7A···N1iii and π···π interactions (Cg···Cgiii = 3.800 (1) Å, Cg represents the C5-N3-C6-C7-N4-C8 ring; symmetry code: iii = 2 - x, 1 - y, 1 - z). The dimers are further interconnected through π···π interactions between Cg and Cgiv [Cg···Cgiv = 4.174 (2) Å, the distance between the closest ring atom and one Cg is 3.597 (2) Å; symmetry code = 1 - x, 1 - y, 1 - z]. The formed chains are further connected through C3—H3A···O3ii(oxynitride) hydrogen bonds to form a layer almost parallel to the ab plane (symmetry code: ii = 2 - x, - y, 1 - z). Along the c axis, the formed layers are stacked and interconnected through C2—H2A···O1i(sulfonyl) interactions to form a three-dimensional framework (Fig. 3, Table 1; symmetry code: i = x, -y + 1/2, z + 1/2).

Related literature top

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 top

The title compound was obtained as a serendipitous byproduct as the 2,2'-dipyrazine sulfide (0.022 g, 0.1 mmol) was dissolved in a mixture of methanol 2 ml and acetonitrile 2 ml to react with Mn(ClO4)2.6H2O (0.036 g, 0.1 mmol) with constantly stirring at room temperature. After three hours, the clear solution was filtrated and kept in air for about one week to yield colourless block crystals (7 mg, 29% yield). We got the the title compound as a matter of the oxidability by perchlorate acid from Mn(ClO4)2.6H2O.

Refinement top

All hydrogen positions were calculated after each cycle of refinement using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The highest peak (0.8 e.Å-3) in the difference Fourier map is located at 1.1 Å from atom N4. The refinement of a model including one H atom at this position led to lower R1 and wR2 values but it is chemically meaningless since there is no counter ion in the crystal structure. A positional disorder of the oxo O atom (partially on atoms O4 and O2) is surely the best solution but in this case too many restraints had to be used in the final refinements to get an acceptable model (with an site-occupancy ratio greater than 0.9:0.1).

Structure description top

Pyridyl based sulfonyl derivatives were widely used in supramolecular assemblies of transition metal complexes (Wan & Mak, 2011). Pyridyl based N-oxide derivatives have also been demonstrated as versatile building blocks to construct supramolecular architectures of various metal complexes (Jia et al., 2008). In the present context, we report the structure of the title compound, a new N-oxide compound derived from 2,2'-sulfonyldipyrazine.

In the title compound, the value of the C1(sp2)—S1—C5(sp2) angle is 103.92 (1)° with two attached pyrazinyl rings exhibiting a dihedral angle of 85.04 (1)°, as shown in Fig. 1. The angular-shaped molecules are arranged along the a axis. As shown in Fig. 2, two adjacent molecules arranged with an inversion center are interconnected through C7—H7A···N1iii and π···π interactions (Cg···Cgiii = 3.800 (1) Å, Cg represents the C5-N3-C6-C7-N4-C8 ring; symmetry code: iii = 2 - x, 1 - y, 1 - z). The dimers are further interconnected through π···π interactions between Cg and Cgiv [Cg···Cgiv = 4.174 (2) Å, the distance between the closest ring atom and one Cg is 3.597 (2) Å; symmetry code = 1 - x, 1 - y, 1 - z]. The formed chains are further connected through C3—H3A···O3ii(oxynitride) hydrogen bonds to form a layer almost parallel to the ab plane (symmetry code: ii = 2 - x, - y, 1 - z). Along the c axis, the formed layers are stacked and interconnected through C2—H2A···O1i(sulfonyl) interactions to form a three-dimensional framework (Fig. 3, Table 1; symmetry code: i = x, -y + 1/2, z + 1/2).

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. The atom-numbering scheme of the title complex. Displacement ellipsoids are drawn at the 35% probability level and H atoms are shown as sticks of arbitrary radii.
[Figure 2] Fig. 2. The hydrogen-bonding (C—H···N) and π···π stacking interactions between parallel chains along the a axis, which are respectively shown as thin red-dashed lines and thick blue-dashed lines (symmetry codes: i = - x + 2, - y + 1, - z + 1; ii = x + 1, y, z).
[Figure 3] Fig. 3. Three-dimensional structure of the title molecule viewed down the a direction. The red dashed lines represent hydrogen-bonding interactions.
2,2'-Sulfonyldipyrazine 4-oxide top
Crystal data top
C8H6N4O3SF(000) = 488
Mr = 238.23Dx = 1.621 Mg m−3
Dm = 1.621 Mg m−3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 365 reflections
a = 7.6860 (16) Åθ = 2.6–28.4°
b = 15.841 (3) ŵ = 0.33 mm−1
c = 9.0624 (14) ÅT = 296 K
β = 117.813 (13)°Needle-like, colourless
V = 975.9 (3) Å30.45 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2429 independent reflections
Radiation source: fine-focus sealed tube1586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −10→10
Tmin = 0.688, Tmax = 1.000k = −21→11
6606 measured reflectionsl = −12→11
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203H-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 parametersΔρmax = 0.85 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C8H6N4O3SV = 975.9 (3) Å3
Mr = 238.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.6860 (16) ŵ = 0.33 mm−1
b = 15.841 (3) ÅT = 296 K
c = 9.0624 (14) Å0.45 × 0.30 × 0.25 mm
β = 117.813 (13)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2429 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		1586 reflections with I > 2σ(I)
Tmin = 0.688, Tmax = 1.000Rint = 0.058
6606 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.203H-atom parameters constrained
S = 1.07Δρmax = 0.85 e Å−3
2429 reflectionsΔρmin = −0.46 e Å−3
145 parameters
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.50844 (11)0.33579 (5)0.25247 (12)0.0436 (3)
N10.8484 (4)0.27476 (19)0.2912 (4)0.0531 (8)
N20.8080 (4)0.12101 (18)0.4199 (4)0.0520 (8)
N30.6907 (4)0.4321 (2)0.5196 (4)0.0540 (8)
N40.7631 (6)0.5635 (2)0.3499 (6)0.0699 (10)
O10.4354 (3)0.35188 (18)0.0788 (3)0.0581 (7)
O20.3755 (4)0.31172 (17)0.3141 (4)0.0627 (8)
O30.7852 (6)0.0494 (2)0.4742 (6)0.0996 (13)
C10.6949 (4)0.25624 (19)0.3152 (4)0.0403 (7)
C20.6667 (5)0.1820 (2)0.3776 (5)0.0494 (9)
H2A0.55520.17320.39100.059*
C30.9681 (5)0.1382 (2)0.4026 (5)0.0535 (9)
H3A1.06850.09850.43510.064*
C40.9844 (5)0.2134 (2)0.3375 (6)0.0582 (10)
H4A1.09590.22290.32440.070*
C50.6391 (4)0.4281 (2)0.3598 (4)0.0416 (8)
C60.7790 (6)0.5037 (3)0.5944 (6)0.0627 (11)
H6A0.81890.51050.70760.075*
C70.8125 (6)0.5678 (3)0.5086 (7)0.0677 (13)
H7A0.87340.61670.56640.081*
C80.6737 (5)0.4914 (2)0.2717 (5)0.0561 (9)
H8A0.63550.48430.15880.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0286 (4)0.0384 (4)0.0661 (6)−0.0005 (3)0.0238 (4)−0.0064 (4)
N10.0336 (13)0.0392 (15)0.090 (2)−0.0016 (11)0.0314 (14)0.0025 (14)
N20.0566 (17)0.0332 (14)0.073 (2)0.0047 (13)0.0357 (16)0.0039 (14)
N30.0531 (17)0.0451 (17)0.062 (2)0.0018 (13)0.0250 (15)−0.0052 (14)
N40.069 (2)0.0405 (17)0.110 (3)−0.0067 (16)0.050 (2)−0.0055 (19)
O10.0378 (12)0.0647 (17)0.0632 (17)0.0072 (11)0.0165 (11)−0.0084 (13)
O20.0493 (14)0.0492 (15)0.109 (2)−0.0070 (12)0.0529 (15)−0.0115 (14)
O30.117 (3)0.0558 (19)0.159 (4)0.020 (2)0.092 (3)0.033 (2)
C10.0313 (14)0.0330 (15)0.0563 (19)−0.0009 (12)0.0203 (13)−0.0058 (14)
C20.0477 (18)0.0394 (17)0.074 (2)0.0008 (14)0.0395 (18)−0.0013 (16)
C30.0350 (16)0.0456 (19)0.072 (2)0.0044 (14)0.0187 (16)−0.0014 (18)
C40.0315 (16)0.0463 (19)0.099 (3)0.0001 (14)0.0318 (18)0.0007 (19)
C50.0311 (14)0.0333 (15)0.062 (2)0.0036 (12)0.0230 (14)−0.0017 (14)
C60.055 (2)0.056 (2)0.068 (3)0.0036 (18)0.0203 (19)−0.017 (2)
C70.047 (2)0.041 (2)0.115 (4)−0.0084 (16)0.038 (2)−0.024 (2)
C80.055 (2)0.045 (2)0.072 (3)0.0007 (16)0.0323 (19)−0.0001 (18)
Geometric parameters (Å, º) top
S1—O11.425 (3)N4—C81.351 (5)
S1—O21.426 (3)C1—C21.366 (5)
S1—C51.784 (3)C2—H2A0.9300
S1—C11.790 (3)C3—C41.362 (6)
N1—C11.328 (4)C3—H3A0.9300
N1—C41.343 (4)C4—H4A0.9300
N2—O31.281 (4)C5—C81.382 (5)
N2—C31.339 (5)C6—C71.374 (7)
N2—C21.368 (4)C6—H6A0.9300
N3—C51.312 (5)C7—H7A0.9300
N3—C61.333 (5)C8—H8A0.9300
N4—C71.306 (6)
O1—S1—O2119.66 (17)N2—C3—C4120.2 (3)
O1—S1—C5106.68 (17)N2—C3—H3A119.9
O2—S1—C5109.23 (16)C4—C3—H3A119.9
O1—S1—C1108.72 (16)N1—C4—C3123.6 (3)
O2—S1—C1107.53 (17)N1—C4—H4A118.2
C5—S1—C1103.92 (14)C3—C4—H4A118.2
C1—N1—C4114.3 (3)N3—C5—C8124.2 (3)
O3—N2—C3121.5 (3)N3—C5—S1116.4 (3)
O3—N2—C2120.0 (3)C8—C5—S1119.4 (3)
C3—N2—C2118.5 (3)N3—C6—C7121.7 (4)
C5—N3—C6114.9 (4)N3—C6—H6A119.1
C7—N4—C8115.9 (4)C7—C6—H6A119.1
N1—C1—C2125.6 (3)N4—C7—C6123.4 (4)
N1—C1—S1115.7 (2)N4—C7—H7A118.3
C2—C1—S1118.6 (2)C6—C7—H7A118.3
C1—C2—N2117.7 (3)N4—C8—C5119.8 (4)
C1—C2—H2A121.1N4—C8—H8A120.1
N2—C2—H2A121.1C5—C8—H8A120.1
C4—N1—C1—C2−1.3 (5)N2—C3—C4—N11.6 (7)
C4—N1—C1—S1−179.2 (3)C6—N3—C5—C81.0 (5)
O1—S1—C1—N159.3 (3)C6—N3—C5—S1−176.7 (3)
O2—S1—C1—N1−169.8 (3)O1—S1—C5—N3169.1 (2)
C5—S1—C1—N1−54.1 (3)O2—S1—C5—N338.4 (3)
O1—S1—C1—C2−118.8 (3)C1—S1—C5—N3−76.1 (3)
O2—S1—C1—C212.1 (3)O1—S1—C5—C8−8.7 (3)
C5—S1—C1—C2127.8 (3)O2—S1—C5—C8−139.4 (3)
N1—C1—C2—N20.1 (6)C1—S1—C5—C8106.1 (3)
S1—C1—C2—N2178.0 (3)C5—N3—C6—C7−0.1 (5)
O3—N2—C2—C1−177.9 (4)C8—N4—C7—C60.5 (6)
C3—N2—C2—C11.9 (5)N3—C6—C7—N4−0.6 (6)
O3—N2—C3—C4177.1 (4)C7—N4—C8—C50.3 (6)
C2—N2—C3—C4−2.8 (6)N3—C5—C8—N4−1.1 (5)
C1—N1—C4—C30.4 (6)S1—C5—C8—N4176.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.932.323.130 (5)146
C3—H3A···O3ii0.932.563.419 (4)153
C7—H7A···N1iii0.932.573.449 (3)157
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC8H6N4O3S
Mr238.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)7.6860 (16), 15.841 (3), 9.0624 (14)
β (°) 117.813 (13)
V (Å3)975.9 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.45 × 0.30 × 0.25
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.688, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6606, 2429, 1586
Rint0.058
(sin θ/λ)max (Å−1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.203, 1.07
No. of reflections2429
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.85, −0.46

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1i0.932.323.130 (5)145.8
C3—H3A···O3ii0.932.563.419 (4)153.4
C7—H7A···N1iii0.932.573.449 (3)157.2
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.
 

Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Beijing Municipality (grant No. 2122011) and the Beijing Municipal Education Commission (KM201210028018) for financial support.

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJia, J. H., Blake, A. J., Champness, N. R., Hubberstey, P., Wilson, C. & Schröder, M. (2008). Inorg. Chem. 47, 8652–8664.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWan, C. Q. & Mak, T. C. W. (2011). New J. Chem. 35, 319–327.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2285
https://doi.org/10.1107/S1600536812028607
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