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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o827.
Published online 2008 April 10. doi:  10.1107/S1600536808009331
PMCID: PMC2961218

2-Acetyl-3-methyl­pyrazine phenyl­sulfonyl­hydrazone

Abstract

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].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0o827-scheme1.jpg

Experimental

Crystal data

  • C13H14N4O2S
  • M r = 290.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o827-efi1.jpg
  • a = 10.9848 (15) Å
  • b = 16.7921 (18) Å
  • c = 7.4817 (10) Å
  • β = 97.264 (1)°
  • V = 1369.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 (2) K
  • 0.50 × 0.28 × 0.14 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.888, T max = 0.967
  • 6807 measured reflections
  • 2402 independent reflections
  • 1499 reflections with I > 2σ(I)
  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.103
  • S = 1.02
  • 2402 reflections
  • 183 parameters
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009331/hb2717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009331/hb2717Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids for the non-hydrogen atoms.

Crystal data

C13H14N4O2SF000 = 608
Mr = 290.34Dx = 1.409 Mg m3
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 mm1
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

Bruker SMART CCD diffractometer2402 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

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 Å3
183 parametersΔρmin = −0.31 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2717).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X.-S., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography