2-Acetyl-pyrazine 4-methyl-thio-semi-carbazone.

The title compound, C(8)H(11)N(5)S, has been prepared by the reaction of 2-acetyl-pyrazine with 4-methyl-3-thio-semi-carbazide. It exists in the thione form and adopts the E configuration. The mol-ecules are connected by the inter-molecular N-H⋯N and N-H⋯S inter-actions.

Related literature

For related literature, see: Hong et al. (2004 ▶); Latheef et al. (2006 ▶); Liberta & West (1992 ▶); Mendes et al. (2001 ▶); Padhye & Kauffman (1985 ▶).

Experimental

Crystal data

C8H11N5S

M = 209.28

Monoclinic,

a = 9.870 (8) Å

b = 5.976 (5) Å

c = 17.517 (14) Å

β = 91.251 (9)°

V = 1032.8 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 296 (2) K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

9944 measured reflections

1919 independent reflections

1595 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.05

1919 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706285X/at2513sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706285X/at2513Isup2.hkl

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

C8H11N5S	F000 = 440
Mr = 209.28	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3140 reflections
a = 9.870 (8) Å	θ = 2.3–26.0º
b = 5.976 (5) Å	µ = 0.28 mm−1
c = 17.517 (14) Å	T = 296 (2) K
β = 91.251 (9)º	Block, colourless
V = 1032.8 (14) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Monochromator: graphite	θmax = 25.5º
T = 296(2) K	θmin = 2.1º
0.3° wide ω scans	h = −11→11
Absorption correction: none	k = −7→7
9944 measured reflections	l = −21→21
1919 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.2669P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1919 reflections	Δρmax = 0.22 e Å−3
129 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.53153 (5)	0.14546 (9)	0.39197 (3)	0.0578 (2)
C1	0.3602 (2)	0.1901 (4)	0.24436 (12)	0.0638 (6)
H1A	0.2945	0.1858	0.2031	0.096*
H1B	0.4483	0.1567	0.2252	0.096*
H1C	0.3610	0.3365	0.2669	0.096*
C2	0.39403 (17)	−0.0043 (3)	0.36625 (9)	0.0403 (4)
C3	0.20657 (16)	−0.4638 (3)	0.43186 (9)	0.0381 (4)
C4	0.27288 (19)	−0.5396 (3)	0.50496 (10)	0.0517 (5)
H4A	0.3690	−0.5166	0.5026	0.078*
H4B	0.2547	−0.6958	0.5125	0.078*
H4C	0.2376	−0.4552	0.5467	0.078*
C5	0.08835 (16)	−0.5912 (3)	0.40117 (9)	0.0373 (4)
C6	0.01556 (17)	−0.5220 (3)	0.33622 (9)	0.0457 (4)
H6A	0.0401	−0.3887	0.3129	0.055*
C7	−0.1190 (2)	−0.8254 (3)	0.34285 (11)	0.0549 (5)
H7A	−0.1901	−0.9129	0.3240	0.066*
C8	−0.0499 (2)	−0.8930 (4)	0.40744 (12)	0.0626 (6)
H8A	−0.0764	−1.0244	0.4313	0.075*
N1	0.32507 (15)	0.0258 (3)	0.30149 (8)	0.0480 (4)
H1D	0.2552	−0.0570	0.2928	0.058*
N2	0.35053 (14)	−0.1701 (2)	0.41299 (8)	0.0453 (4)
H2A	0.3907	−0.1941	0.4563	0.054*
N3	0.24209 (14)	−0.2982 (2)	0.39019 (8)	0.0416 (4)
N4	−0.08728 (15)	−0.6382 (3)	0.30628 (9)	0.0517 (4)
N5	0.05389 (16)	−0.7775 (3)	0.43754 (9)	0.0536 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0550 (3)	0.0710 (4)	0.0472 (3)	−0.0316 (3)	−0.0039 (2)	−0.0010 (2)
C1	0.0728 (14)	0.0604 (13)	0.0579 (12)	−0.0125 (11)	−0.0085 (10)	0.0176 (10)
C2	0.0397 (9)	0.0426 (10)	0.0385 (9)	−0.0058 (7)	0.0000 (7)	−0.0041 (7)
C3	0.0383 (9)	0.0405 (9)	0.0352 (8)	−0.0057 (7)	−0.0026 (7)	−0.0030 (7)
C4	0.0545 (11)	0.0562 (12)	0.0439 (10)	−0.0144 (9)	−0.0136 (8)	0.0051 (9)
C5	0.0384 (9)	0.0394 (9)	0.0339 (8)	−0.0053 (7)	−0.0001 (7)	−0.0016 (7)
C6	0.0470 (10)	0.0499 (11)	0.0397 (9)	−0.0115 (8)	−0.0073 (8)	0.0044 (8)
C7	0.0489 (11)	0.0626 (13)	0.0532 (11)	−0.0211 (9)	−0.0035 (9)	−0.0084 (10)
C8	0.0685 (14)	0.0562 (13)	0.0627 (13)	−0.0295 (11)	−0.0104 (10)	0.0107 (10)
N1	0.0479 (9)	0.0490 (9)	0.0466 (9)	−0.0134 (7)	−0.0081 (7)	0.0070 (7)
N2	0.0457 (8)	0.0504 (9)	0.0393 (8)	−0.0180 (7)	−0.0099 (6)	0.0051 (7)
N3	0.0392 (8)	0.0452 (8)	0.0402 (8)	−0.0113 (6)	−0.0050 (6)	−0.0007 (6)
N4	0.0468 (9)	0.0641 (11)	0.0435 (8)	−0.0125 (8)	−0.0099 (7)	−0.0018 (8)
N5	0.0572 (10)	0.0522 (9)	0.0509 (9)	−0.0197 (8)	−0.0109 (7)	0.0117 (8)

S1—C2	1.6789 (19)	C5—N5	1.331 (2)
C1—N1	1.449 (2)	C5—C6	1.395 (2)
C1—H1A	0.9600	C6—N4	1.328 (2)
C1—H1B	0.9600	C6—H6A	0.9300
C1—H1C	0.9600	C7—N4	1.330 (3)
C2—N1	1.322 (2)	C7—C8	1.369 (3)
C2—N2	1.361 (2)	C7—H7A	0.9300
C3—N3	1.283 (2)	C8—N5	1.334 (2)
C3—C5	1.484 (2)	C8—H8A	0.9300
C3—C4	1.496 (2)	N1—H1D	0.8600
C4—H4A	0.9600	N2—N3	1.368 (2)
C4—H4B	0.9600	N2—H2A	0.8600
C4—H4C	0.9600
N1—C1—H1A	109.5	C6—C5—C3	122.00 (15)
N1—C1—H1B	109.5	N4—C6—C5	122.84 (17)
H1A—C1—H1B	109.5	N4—C6—H6A	118.6
N1—C1—H1C	109.5	C5—C6—H6A	118.6
H1A—C1—H1C	109.5	N4—C7—C8	121.85 (17)
H1B—C1—H1C	109.5	N4—C7—H7A	119.1
N1—C2—N2	116.88 (15)	C8—C7—H7A	119.1
N1—C2—S1	123.73 (14)	N5—C8—C7	122.59 (18)
N2—C2—S1	119.38 (13)	N5—C8—H8A	118.7
N3—C3—C5	114.34 (14)	C7—C8—H8A	118.7
N3—C3—C4	126.94 (15)	C2—N1—C1	123.93 (16)
C5—C3—C4	118.71 (15)	C2—N1—H1D	118.0
C3—C4—H4A	109.5	C1—N1—H1D	118.0
C3—C4—H4B	109.5	C2—N2—N3	119.13 (14)
H4A—C4—H4B	109.5	C2—N2—H2A	120.4
C3—C4—H4C	109.5	N3—N2—H2A	120.4
H4A—C4—H4C	109.5	C3—N3—N2	119.15 (14)
H4B—C4—H4C	109.5	C6—N4—C7	115.83 (16)
N5—C5—C6	120.41 (15)	C5—N5—C8	116.45 (16)
N5—C5—C3	117.58 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···N4i	0.86	2.42	3.137 (3)	141
N2—H2A···S1ii	0.86	2.77	3.588 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯N4i	0.86	2.42	3.137 (3)	141
N2—H2A⋯S1ii	0.86	2.77	3.588 (3)	161

Symmetry codes: (i) ; (ii) .