2-Acetyl-3-methyl­pyrazine phenyl­sulfonyl­hydrazone

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

doi:10.1107/S1600536808009331

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o827

doi:10.1107/S1600536808009331

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2-Acetyl-3-methylpyrazine phenylsulfonylhydrazone

Xi-Shi Tai,^a Yi-Min Feng ^a and Fan-Yuan Kong ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 6 April 2008; accepted 6 April 2008; online 10 April 2008)

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 ).

Experimental

Crystal data

C₁₃H₁₄N₄O₂S
M_r = 290.34
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.103
S = 1.02
2402 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.34	3.027 (3)	137
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

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

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

checkCIF report

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.

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

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

C₁₃H₁₄N₄O₂S	F(000) = 608
M_r = 290.34	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1439 reflections
a = 10.9848 (15) Å	θ = 3.0–22.9°
b = 16.7921 (18) Å	µ = 0.24 mm⁻¹
c = 7.4817 (10) Å	T = 298 K
β = 97.264 (1)°	Block, colourless
V = 1369.0 (3) Å³	0.50 × 0.28 × 0.14 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2402 independent reflections
Radiation source: fine-focus sealed tube	1499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→8
T_min = 0.888, T_max = 0.967	k = −19→17
6807 measured reflections	l = −8→8

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.036P)²] where P = (F_o² + 2F_c²)/3
2402 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₃H₁₄N₄O₂S	V = 1369.0 (3) Å³
M_r = 290.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9848 (15) Å	µ = 0.24 mm⁻¹
b = 16.7921 (18) Å	T = 298 K
c = 7.4817 (10) Å	0.50 × 0.28 × 0.14 mm
β = 97.264 (1)°

Data collection top

Bruker SMART CCD diffractometer	2402 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1499 reflections with I > 2σ(I)
T_min = 0.888, T_max = 0.967	R_int = 0.061
6807 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
2402 reflections	Δρ_min = −0.31 e Å⁻³
183 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.76385 (18)	0.24028 (12)	0.7039 (3)	0.0401 (6)
H1	0.7785	0.2885	0.7389	0.048*
N2	0.64583 (19)	0.21106 (12)	0.6591 (3)	0.0386 (6)
N3	0.3511 (2)	0.28276 (13)	0.5461 (3)	0.0504 (7)
N4	0.2852 (2)	0.12465 (14)	0.5560 (3)	0.0552 (7)
O1	0.98156 (16)	0.21805 (11)	0.7451 (3)	0.0528 (6)
O2	0.85153 (17)	0.14561 (10)	0.5061 (2)	0.0508 (5)
S1	0.87236 (6)	0.17593 (4)	0.68486 (10)	0.0412 (2)
C1	0.8548 (2)	0.09773 (15)	0.8320 (4)	0.0385 (7)
C2	0.7922 (3)	0.03023 (16)	0.7692 (4)	0.0539 (8)
H2	0.7631	0.0249	0.6475	0.065*
C3	0.7734 (3)	−0.02929 (19)	0.8895 (6)	0.0704 (10)
H3A	0.7318	−0.0754	0.8494	0.084*
C4	0.8160 (3)	−0.0204 (2)	1.0670 (6)	0.0723 (11)
H4	0.8010	−0.0602	1.1479	0.087*
C5	0.8807 (3)	0.0460 (2)	1.1294 (4)	0.0660 (10)
H5	0.9114	0.0505	1.2506	0.079*
C6	0.8996 (3)	0.10584 (17)	1.0104 (4)	0.0516 (8)
H6	0.9425	0.1515	1.0508	0.062*
C7	0.5726 (3)	0.34525 (15)	0.7167 (4)	0.0500 (8)
H7A	0.6031	0.3497	0.8423	0.075*
H7B	0.4948	0.3718	0.6935	0.075*
H7C	0.6298	0.3694	0.6462	0.075*
C8	0.5571 (2)	0.25952 (15)	0.6673 (3)	0.0361 (7)
C9	0.4326 (2)	0.22753 (15)	0.6112 (3)	0.0370 (7)
C10	0.3985 (3)	0.14763 (16)	0.6207 (4)	0.0427 (7)
C11	0.2074 (3)	0.17989 (19)	0.4865 (4)	0.0581 (9)
H11	0.1286	0.1650	0.4380	0.070*
C12	0.2400 (3)	0.2581 (2)	0.4845 (4)	0.0588 (9)
H12	0.1817	0.2953	0.4381	0.071*
C13	0.4793 (3)	0.08310 (16)	0.7054 (4)	0.0641 (10)
H13A	0.4296	0.0395	0.7368	0.096*
H13B	0.5272	0.1031	0.8121	0.096*
H13C	0.5329	0.0651	0.6220	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0289 (14)	0.0326 (12)	0.0566 (16)	−0.0015 (10)	−0.0026 (11)	−0.0017 (11)
N2	0.0279 (14)	0.0445 (13)	0.0413 (15)	−0.0002 (11)	−0.0037 (11)	−0.0015 (11)
N3	0.0346 (16)	0.0528 (15)	0.0610 (18)	0.0029 (12)	−0.0043 (13)	0.0027 (13)
N4	0.0402 (17)	0.0594 (16)	0.0645 (18)	−0.0082 (13)	0.0006 (13)	−0.0014 (14)
O1	0.0291 (12)	0.0601 (13)	0.0667 (14)	−0.0069 (9)	−0.0033 (10)	0.0065 (11)
O2	0.0515 (13)	0.0615 (13)	0.0383 (12)	0.0083 (10)	0.0008 (9)	−0.0039 (10)
S1	0.0308 (4)	0.0479 (4)	0.0439 (5)	0.0027 (3)	0.0003 (3)	0.0018 (4)
C1	0.0321 (17)	0.0405 (16)	0.0429 (19)	0.0085 (12)	0.0042 (13)	−0.0010 (14)
C2	0.044 (2)	0.0517 (19)	0.063 (2)	0.0042 (15)	−0.0036 (16)	0.0007 (18)
C3	0.065 (2)	0.049 (2)	0.096 (3)	−0.0003 (16)	0.007 (2)	0.013 (2)
C4	0.080 (3)	0.057 (2)	0.086 (3)	0.019 (2)	0.037 (2)	0.025 (2)
C5	0.085 (3)	0.069 (2)	0.047 (2)	0.034 (2)	0.0166 (19)	0.004 (2)
C6	0.061 (2)	0.0464 (18)	0.048 (2)	0.0134 (15)	0.0079 (16)	−0.0043 (16)
C7	0.0441 (19)	0.0471 (18)	0.056 (2)	0.0026 (13)	−0.0027 (15)	−0.0038 (15)
C8	0.0340 (17)	0.0413 (16)	0.0323 (17)	0.0031 (13)	0.0014 (13)	0.0011 (13)
C9	0.0316 (17)	0.0447 (17)	0.0342 (17)	0.0030 (13)	0.0019 (13)	−0.0008 (14)
C10	0.0374 (18)	0.0484 (17)	0.0422 (18)	−0.0012 (14)	0.0045 (14)	−0.0009 (15)
C11	0.0324 (19)	0.073 (2)	0.066 (2)	−0.0047 (17)	−0.0047 (16)	−0.0056 (19)
C12	0.032 (2)	0.069 (2)	0.071 (2)	0.0059 (16)	−0.0084 (16)	0.0003 (18)
C13	0.050 (2)	0.0490 (19)	0.090 (3)	−0.0034 (15)	−0.0032 (18)	0.0134 (19)

Geometric parameters (Å, º) top

N1—N2	1.387 (3)	C4—H4	0.9300
N1—S1	1.628 (2)	C5—C6	1.376 (4)
N1—H1	0.8600	C5—H5	0.9300
N2—C8	1.277 (3)	C6—H6	0.9300
N3—C12	1.316 (3)	C7—C8	1.491 (3)
N3—C9	1.337 (3)	C7—H7A	0.9600
N4—C11	1.323 (3)	C7—H7B	0.9600
N4—C10	1.334 (3)	C7—H7C	0.9600
O1—S1	1.4163 (18)	C8—C9	1.480 (3)
O2—S1	1.4220 (19)	C9—C10	1.397 (3)
S1—C1	1.740 (3)	C10—C13	1.490 (3)
C1—C6	1.370 (4)	C11—C12	1.361 (4)
C1—C2	1.377 (3)	C11—H11	0.9300
C2—C3	1.378 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.359 (5)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.372 (4)

N2—N1—S1	114.60 (16)	C5—C6—H6	120.2
N2—N1—H1	122.7	C8—C7—H7A	109.5
S1—N1—H1	122.7	C8—C7—H7B	109.5
C8—N2—N1	117.3 (2)	H7A—C7—H7B	109.5
C12—N3—C9	117.2 (2)	C8—C7—H7C	109.5
C11—N4—C10	117.8 (3)	H7A—C7—H7C	109.5
O1—S1—O2	120.49 (13)	H7B—C7—H7C	109.5
O1—S1—N1	103.92 (12)	N2—C8—C9	116.0 (2)
O2—S1—N1	106.70 (11)	N2—C8—C7	124.3 (2)
O1—S1—C1	109.44 (12)	C9—C8—C7	119.5 (2)
O2—S1—C1	107.89 (12)	N3—C9—C10	120.9 (2)
N1—S1—C1	107.71 (12)	N3—C9—C8	113.8 (2)
C6—C1—C2	121.1 (3)	C10—C9—C8	125.3 (2)
C6—C1—S1	119.1 (2)	N4—C10—C9	120.2 (2)
C2—C1—S1	119.7 (2)	N4—C10—C13	115.0 (2)
C1—C2—C3	118.9 (3)	C9—C10—C13	124.8 (2)
C1—C2—H2	120.6	N4—C11—C12	121.5 (3)
C3—C2—H2	120.6	N4—C11—H11	119.2
C4—C3—C2	119.8 (3)	C12—C11—H11	119.2
C4—C3—H3A	120.1	N3—C12—C11	122.3 (3)
C2—C3—H3A	120.1	N3—C12—H12	118.9
C3—C4—C5	121.4 (3)	C11—C12—H12	118.9
C3—C4—H4	119.3	C10—C13—H13A	109.5
C5—C4—H4	119.3	C10—C13—H13B	109.5
C4—C5—C6	119.2 (3)	H13A—C13—H13B	109.5
C4—C5—H5	120.4	C10—C13—H13C	109.5
C6—C5—H5	120.4	H13A—C13—H13C	109.5
C1—C6—C5	119.5 (3)	H13B—C13—H13C	109.5
C1—C6—H6	120.2

S1—N1—N2—C8	−178.3 (2)	N1—N2—C8—C9	177.5 (2)
N2—N1—S1—O1	−177.34 (18)	N1—N2—C8—C7	1.7 (4)
N2—N1—S1—O2	54.3 (2)	C12—N3—C9—C10	−2.9 (4)
N2—N1—S1—C1	−61.3 (2)	C12—N3—C9—C8	176.5 (3)
O1—S1—C1—C6	30.8 (3)	N2—C8—C9—N3	−152.2 (3)
O2—S1—C1—C6	163.6 (2)	C7—C8—C9—N3	23.8 (4)
N1—S1—C1—C6	−81.6 (2)	N2—C8—C9—C10	27.2 (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—C2	96.0 (2)	C11—N4—C10—C13	177.0 (3)
C6—C1—C2—C3	0.9 (4)	N3—C9—C10—N4	3.5 (4)
S1—C1—C2—C3	−176.5 (2)	C8—C9—C10—N4	−175.9 (3)
C1—C2—C3—C4	0.3 (5)	N3—C9—C10—C13	−174.4 (3)
C2—C3—C4—C5	−1.8 (5)	C8—C9—C10—C13	6.3 (5)
C3—C4—C5—C6	2.0 (5)	C10—N4—C11—C12	−1.6 (5)
C2—C1—C6—C5	−0.7 (4)	C9—N3—C12—C11	0.2 (5)
S1—C1—C6—C5	176.8 (2)	N4—C11—C12—N3	2.1 (5)
C4—C5—C6—C1	−0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.34	3.027 (3)	137

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₄O₂S
M_r	290.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.9848 (15), 16.7921 (18), 7.4817 (10)
β (°)	97.264 (1)
V (Å³)	1369.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.28 × 0.14

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.888, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	6807, 2402, 1499
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.103, 1.03
No. of reflections	2402
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.34	3.027 (3)	137

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750. Web of Science CSD CrossRef IUCr Journals Google Scholar