supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

hb2717 scheme

Acta Cryst. (2008). E64, o827    [ doi:10.1107/S1600536808009331 ]

2-Acetyl-3-methylpyrazine phenylsulfonylhydrazone

X.-S. Tai, Y.-M. Feng and F.-Y. Kong

Abstract top

In the title compound, C13H14N4O2S, the dihedral angle between the aromatic rings is 55.42 (14)°. In the crystal structure, an N-H...O hydrogen bond leads to chains of molecules along [001].

Comment top

As part of our ongoing studies of aroylhydrazones as possible ligands (Tai et al., 2008), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The dihedral angle between the aromatic ring planes is 55.42 (14)°. Otherwise, the geometrical parameters for (I) are normal. In the crystal of (I), an N-H···O hydrogen bond (Table 1) leads to [001] chains.

Related literature top

For related literature, see: Tai et al. (2008).

Experimental top

1 mmol of 2-Acetyl-3-methylpyrazine (1 mmol) was added to a solution of benzenesulfonyl hydrazide (1 mmol) in 5 ml of 95% ethanol. The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 67%). Clear blocks of (I) were obtained by evaporation from a methanol solution after 3 days.

Refinement top

The H atoms were placed geometrically (C—H = 0.93–0.96 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids for the non-hydrogen atoms.
2-Acetyl-3-methylpyrazine phenylsulfonylhydrazone top
Crystal data top
C13H14N4O2SF000 = 608
Mr = 290.34Dx = 1.409 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1439 reflections
a = 10.9848 (15) Åθ = 3.0–22.9º
b = 16.7921 (18) ŵ = 0.24 mm−1
c = 7.4817 (10) ÅT = 298 (2) K
β = 97.264 (1)ºBlock, colourless
V = 1369.0 (3) Å30.50 × 0.28 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		2402 independent reflections
Radiation source: fine-focus sealed tube1499 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −13→8
Tmin = 0.888, Tmax = 0.967k = −19→17
6807 measured reflectionsl = −8→8
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.103  w = 1/[σ2(Fo2) + (0.036P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2402 reflectionsΔρmax = 0.32 e Å−3
183 parametersΔρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C13H14N4O2SV = 1369.0 (3) Å3
Mr = 290.34Z = 4
Monoclinic, P21/cMo Kα
a = 10.9848 (15) ŵ = 0.24 mm−1
b = 16.7921 (18) ÅT = 298 (2) K
c = 7.4817 (10) Å0.50 × 0.28 × 0.14 mm
β = 97.264 (1)º
Data collection top
Bruker SMART CCD
diffractometer		2402 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1499 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.967Rint = 0.061
6807 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046183 parameters
wR(F2) = 0.103H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å−3
2402 reflectionsΔρmin = −0.31 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.76385 (18)0.24028 (12)0.7039 (3)0.0401 (6)
H10.77850.28850.73890.048*
N20.64583 (19)0.21106 (12)0.6591 (3)0.0386 (6)
N30.3511 (2)0.28276 (13)0.5461 (3)0.0504 (7)
N40.2852 (2)0.12465 (14)0.5560 (3)0.0552 (7)
O10.98156 (16)0.21805 (11)0.7451 (3)0.0528 (6)
O20.85153 (17)0.14561 (10)0.5061 (2)0.0508 (5)
S10.87236 (6)0.17593 (4)0.68486 (10)0.0412 (2)
C10.8548 (2)0.09773 (15)0.8320 (4)0.0385 (7)
C20.7922 (3)0.03023 (16)0.7692 (4)0.0539 (8)
H20.76310.02490.64750.065*
C30.7734 (3)−0.02929 (19)0.8895 (6)0.0704 (10)
H3A0.7318−0.07540.84940.084*
C40.8160 (3)−0.0204 (2)1.0670 (6)0.0723 (11)
H40.8010−0.06021.14790.087*
C50.8807 (3)0.0460 (2)1.1294 (4)0.0660 (10)
H50.91140.05051.25060.079*
C60.8996 (3)0.10584 (17)1.0104 (4)0.0516 (8)
H60.94250.15151.05080.062*
C70.5726 (3)0.34525 (15)0.7167 (4)0.0500 (8)
H7A0.60310.34970.84230.075*
H7B0.49480.37180.69350.075*
H7C0.62980.36940.64620.075*
C80.5571 (2)0.25952 (15)0.6673 (3)0.0361 (7)
C90.4326 (2)0.22753 (15)0.6112 (3)0.0370 (7)
C100.3985 (3)0.14763 (16)0.6207 (4)0.0427 (7)
C110.2074 (3)0.17989 (19)0.4865 (4)0.0581 (9)
H110.12860.16500.43800.070*
C120.2400 (3)0.2581 (2)0.4845 (4)0.0588 (9)
H120.18170.29530.43810.071*
C130.4793 (3)0.08310 (16)0.7054 (4)0.0641 (10)
H13A0.42960.03950.73680.096*
H13B0.52720.10310.81210.096*
H13C0.53290.06510.62200.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0289 (14)0.0326 (12)0.0566 (16)−0.0015 (10)−0.0026 (11)−0.0017 (11)
N20.0279 (14)0.0445 (13)0.0413 (15)−0.0002 (11)−0.0037 (11)−0.0015 (11)
N30.0346 (16)0.0528 (15)0.0610 (18)0.0029 (12)−0.0043 (13)0.0027 (13)
N40.0402 (17)0.0594 (16)0.0645 (18)−0.0082 (13)0.0006 (13)−0.0014 (14)
O10.0291 (12)0.0601 (13)0.0667 (14)−0.0069 (9)−0.0033 (10)0.0065 (11)
O20.0515 (13)0.0615 (13)0.0383 (12)0.0083 (10)0.0008 (9)−0.0039 (10)
S10.0308 (4)0.0479 (4)0.0439 (5)0.0027 (3)0.0003 (3)0.0018 (4)
C10.0321 (17)0.0405 (16)0.0429 (19)0.0085 (12)0.0042 (13)−0.0010 (14)
C20.044 (2)0.0517 (19)0.063 (2)0.0042 (15)−0.0036 (16)0.0007 (18)
C30.065 (2)0.049 (2)0.096 (3)−0.0003 (16)0.007 (2)0.013 (2)
C40.080 (3)0.057 (2)0.086 (3)0.019 (2)0.037 (2)0.025 (2)
C50.085 (3)0.069 (2)0.047 (2)0.034 (2)0.0166 (19)0.004 (2)
C60.061 (2)0.0464 (18)0.048 (2)0.0134 (15)0.0079 (16)−0.0043 (16)
C70.0441 (19)0.0471 (18)0.056 (2)0.0026 (13)−0.0027 (15)−0.0038 (15)
C80.0340 (17)0.0413 (16)0.0323 (17)0.0031 (13)0.0014 (13)0.0011 (13)
C90.0316 (17)0.0447 (17)0.0342 (17)0.0030 (13)0.0019 (13)−0.0008 (14)
C100.0374 (18)0.0484 (17)0.0422 (18)−0.0012 (14)0.0045 (14)−0.0009 (15)
C110.0324 (19)0.073 (2)0.066 (2)−0.0047 (17)−0.0047 (16)−0.0056 (19)
C120.032 (2)0.069 (2)0.071 (2)0.0059 (16)−0.0084 (16)0.0003 (18)
C130.050 (2)0.0490 (19)0.090 (3)−0.0034 (15)−0.0032 (18)0.0134 (19)
Geometric parameters (Å, °) top
N1—N21.387 (3)C4—H40.9300
N1—S11.628 (2)C5—C61.376 (4)
N1—H10.8600C5—H50.9300
N2—C81.277 (3)C6—H60.9300
N3—C121.316 (3)C7—C81.491 (3)
N3—C91.337 (3)C7—H7A0.9600
N4—C111.323 (3)C7—H7B0.9600
N4—C101.334 (3)C7—H7C0.9600
O1—S11.4163 (18)C8—C91.480 (3)
O2—S11.4220 (19)C9—C101.397 (3)
S1—C11.740 (3)C10—C131.490 (3)
C1—C61.370 (4)C11—C121.361 (4)
C1—C21.377 (3)C11—H110.9300
C2—C31.378 (4)C12—H120.9300
C2—H20.9300C13—H13A0.9600
C3—C41.359 (5)C13—H13B0.9600
C3—H3A0.9300C13—H13C0.9600
C4—C51.372 (4)
N2—N1—S1114.60 (16)C5—C6—H6120.2
N2—N1—H1122.7C8—C7—H7A109.5
S1—N1—H1122.7C8—C7—H7B109.5
C8—N2—N1117.3 (2)H7A—C7—H7B109.5
C12—N3—C9117.2 (2)C8—C7—H7C109.5
C11—N4—C10117.8 (3)H7A—C7—H7C109.5
O1—S1—O2120.49 (13)H7B—C7—H7C109.5
O1—S1—N1103.92 (12)N2—C8—C9116.0 (2)
O2—S1—N1106.70 (11)N2—C8—C7124.3 (2)
O1—S1—C1109.44 (12)C9—C8—C7119.5 (2)
O2—S1—C1107.89 (12)N3—C9—C10120.9 (2)
N1—S1—C1107.71 (12)N3—C9—C8113.8 (2)
C6—C1—C2121.1 (3)C10—C9—C8125.3 (2)
C6—C1—S1119.1 (2)N4—C10—C9120.2 (2)
C2—C1—S1119.7 (2)N4—C10—C13115.0 (2)
C1—C2—C3118.9 (3)C9—C10—C13124.8 (2)
C1—C2—H2120.6N4—C11—C12121.5 (3)
C3—C2—H2120.6N4—C11—H11119.2
C4—C3—C2119.8 (3)C12—C11—H11119.2
C4—C3—H3A120.1N3—C12—C11122.3 (3)
C2—C3—H3A120.1N3—C12—H12118.9
C3—C4—C5121.4 (3)C11—C12—H12118.9
C3—C4—H4119.3C10—C13—H13A109.5
C5—C4—H4119.3C10—C13—H13B109.5
C4—C5—C6119.2 (3)H13A—C13—H13B109.5
C4—C5—H5120.4C10—C13—H13C109.5
C6—C5—H5120.4H13A—C13—H13C109.5
C1—C6—C5119.5 (3)H13B—C13—H13C109.5
C1—C6—H6120.2
S1—N1—N2—C8−178.3 (2)N1—N2—C8—C9177.5 (2)
N2—N1—S1—O1−177.34 (18)N1—N2—C8—C71.7 (4)
N2—N1—S1—O254.3 (2)C12—N3—C9—C10−2.9 (4)
N2—N1—S1—C1−61.3 (2)C12—N3—C9—C8176.5 (3)
O1—S1—C1—C630.8 (3)N2—C8—C9—N3−152.2 (3)
O2—S1—C1—C6163.6 (2)C7—C8—C9—N323.8 (4)
N1—S1—C1—C6−81.6 (2)N2—C8—C9—C1027.2 (4)
O1—S1—C1—C2−151.7 (2)C7—C8—C9—C10−156.8 (3)
O2—S1—C1—C2−18.9 (3)C11—N4—C10—C9−1.1 (4)
N1—S1—C1—C296.0 (2)C11—N4—C10—C13177.0 (3)
C6—C1—C2—C30.9 (4)N3—C9—C10—N43.5 (4)
S1—C1—C2—C3−176.5 (2)C8—C9—C10—N4−175.9 (3)
C1—C2—C3—C40.3 (5)N3—C9—C10—C13−174.4 (3)
C2—C3—C4—C5−1.8 (5)C8—C9—C10—C136.3 (5)
C3—C4—C5—C62.0 (5)C10—N4—C11—C12−1.6 (5)
C2—C1—C6—C5−0.7 (4)C9—N3—C12—C110.2 (5)
S1—C1—C6—C5176.8 (2)N4—C11—C12—N32.1 (5)
C4—C5—C6—C1−0.7 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.343.027 (3)137
Symmetry codes: (i) x, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.343.027 (3)137
Symmetry codes: (i) x, −y+1/2, z+1/2.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong (Y2007B60), the Science and Technology Foundation of Weifang and Weifang University for research grants.

references
References top

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tai, X.-S., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750.