5-Methyl-N-(1,3-thia-zol-2-yl)isoxazole-4-carboxamide.

In the title compound, C8H7N3O2S, the dihedral angle between the thia-zol and isoxazole rings is 34.08 (13)°. In the crystal, the mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers, and C-H⋯O inter-actions, resulting in chains along the b-axis direction.

Related literature

For background to isoxazole-containing drugs, see: Shaw et al. (2011 ▶); Schattenkirchner (2000 ▶); Huang et al. (2003 ▶). For the crystal structure of a related compound, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C8H7N3O2S

M = 209.23

Monoclinic,

a = 8.8460 (18) Å

b = 10.742 (2) Å

c = 10.024 (2) Å

β = 107.27 (3)°

V = 909.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.907, T max = 0.968

3462 measured reflections

1676 independent reflections

1298 reflections with I > 2σ(I)

R int = 0.060

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.00

1676 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius,1994) ▶; cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813012105/pv2631sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012105/pv2631Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012105/pv2631Isup3.cml

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

C8H7N3O2S	F(000) = 432
Mr = 209.23	Dx = 1.528 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.8460 (18) Å	θ = 10–13°
b = 10.742 (2) Å	µ = 0.33 mm−1
c = 10.024 (2) Å	T = 293 K
β = 107.27 (3)°	Block, yellow
V = 909.6 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1298 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
Graphite monochromator	θmax = 25.4°, θmin = 2.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.907, Tmax = 0.968	l = −12→11
3462 measured reflections	3 standard reflections every 200 reflections
1676 independent reflections	intensity decay: 1%

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.1P)2 + 0.180P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1676 reflections	Δρmax = 0.38 e Å−3
128 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (5)

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
S	0.27245 (9)	0.30807 (7)	0.46506 (9)	0.0578 (3)
O1	0.5024 (2)	0.36916 (17)	0.3546 (2)	0.0517 (6)
N1	0.3255 (3)	0.0745 (2)	0.5154 (2)	0.0463 (6)
C1	0.1512 (4)	0.2266 (3)	0.5378 (4)	0.0629 (9)
H1A	0.0654	0.2605	0.5607	0.075*
O2	0.8730 (2)	0.2660 (2)	0.1941 (2)	0.0532 (6)
N2	0.5011 (2)	0.16438 (19)	0.4088 (2)	0.0390 (5)
H2A	0.5475	0.0938	0.4106	0.047*
C2	0.1958 (3)	0.1078 (3)	0.5573 (3)	0.0558 (8)
H2B	0.1426	0.0507	0.5969	0.067*
N3	0.8148 (3)	0.1439 (3)	0.1552 (3)	0.0569 (7)
C3	0.3761 (3)	0.1719 (2)	0.4640 (3)	0.0371 (6)
C4	0.5547 (3)	0.2644 (2)	0.3512 (3)	0.0358 (5)
C5	0.6762 (3)	0.2373 (2)	0.2825 (2)	0.0349 (5)
C6	0.6993 (3)	0.1306 (3)	0.2088 (3)	0.0459 (6)
H6A	0.6384	0.0587	0.1998	0.055*
C7	0.7873 (3)	0.3192 (2)	0.2679 (3)	0.0395 (6)
C8	0.8309 (4)	0.4479 (3)	0.3178 (3)	0.0546 (7)
H8A	0.9169	0.4761	0.2855	0.082*
H8B	0.8626	0.4493	0.4180	0.082*
H8C	0.7413	0.5018	0.2821	0.082*

	U11	U22	U33	U12	U13	U23
S	0.0540 (5)	0.0548 (5)	0.0796 (6)	0.0179 (3)	0.0427 (4)	0.0136 (4)
O1	0.0510 (12)	0.0391 (10)	0.0740 (14)	0.0077 (8)	0.0325 (10)	0.0069 (9)
N1	0.0408 (12)	0.0511 (13)	0.0544 (13)	0.0009 (10)	0.0255 (10)	0.0066 (11)
C1	0.0458 (17)	0.081 (2)	0.076 (2)	0.0194 (16)	0.0384 (16)	0.0196 (18)
O2	0.0447 (11)	0.0687 (13)	0.0561 (12)	−0.0065 (9)	0.0302 (9)	−0.0037 (10)
N2	0.0395 (11)	0.0359 (10)	0.0499 (12)	0.0032 (9)	0.0260 (10)	0.0014 (9)
C2	0.0403 (15)	0.076 (2)	0.0595 (17)	0.0020 (14)	0.0282 (13)	0.0169 (15)
N3	0.0598 (15)	0.0630 (15)	0.0570 (15)	0.0005 (13)	0.0312 (12)	−0.0131 (12)
C3	0.0320 (12)	0.0434 (14)	0.0378 (13)	0.0024 (10)	0.0133 (10)	−0.0014 (10)
C4	0.0314 (12)	0.0372 (12)	0.0410 (13)	0.0014 (10)	0.0144 (10)	−0.0008 (10)
C5	0.0329 (12)	0.0382 (13)	0.0356 (12)	0.0004 (10)	0.0132 (10)	0.0014 (10)
C6	0.0498 (15)	0.0436 (14)	0.0482 (15)	−0.0031 (12)	0.0207 (12)	−0.0060 (12)
C7	0.0358 (13)	0.0501 (15)	0.0351 (13)	0.0006 (11)	0.0143 (11)	0.0039 (10)
C8	0.0531 (17)	0.0512 (16)	0.0616 (18)	−0.0123 (13)	0.0203 (14)	0.0034 (14)

S—C1	1.707 (3)	N2—H2A	0.8600
S—C3	1.729 (2)	C2—H2B	0.9300
O1—C4	1.222 (3)	N3—C6	1.296 (4)
N1—C3	1.303 (3)	C4—C5	1.468 (3)
N1—C2	1.381 (3)	C5—C7	1.358 (4)
C1—C2	1.332 (5)	C5—C6	1.411 (4)
C1—H1A	0.9300	C6—H6A	0.9300
O2—C7	1.334 (3)	C7—C8	1.483 (4)
O2—N3	1.420 (3)	C8—H8A	0.9600
N2—C4	1.369 (3)	C8—H8B	0.9600
N2—C3	1.377 (3)	C8—H8C	0.9600
C1—S—C3	88.31 (14)	O1—C4—C5	122.1 (2)
C3—N1—C2	109.1 (2)	N2—C4—C5	115.9 (2)
C2—C1—S	111.0 (2)	C7—C5—C6	104.4 (2)
C2—C1—H1A	124.5	C7—C5—C4	125.2 (2)
S—C1—H1A	124.5	C6—C5—C4	130.3 (2)
C7—O2—N3	109.2 (2)	N3—C6—C5	112.4 (3)
C4—N2—C3	122.9 (2)	N3—C6—H6A	123.8
C4—N2—H2A	118.5	C5—C6—H6A	123.8
C3—N2—H2A	118.5	O2—C7—C5	109.3 (2)
C1—C2—N1	116.1 (3)	O2—C7—C8	117.0 (2)
C1—C2—H2B	122.0	C5—C7—C8	133.7 (3)
N1—C2—H2B	122.0	C7—C8—H8A	109.5
C6—N3—O2	104.7 (2)	C7—C8—H8B	109.5
N1—C3—N2	121.6 (2)	H8A—C8—H8B	109.5
N1—C3—S	115.55 (19)	C7—C8—H8C	109.5
N2—C3—S	122.86 (19)	H8A—C8—H8C	109.5
O1—C4—N2	122.0 (2)	H8B—C8—H8C	109.5
C3—S—C1—C2	0.8 (3)	N2—C4—C5—C7	−152.8 (2)
S—C1—C2—N1	−0.6 (4)	O1—C4—C5—C6	−145.8 (3)
C3—N1—C2—C1	−0.1 (4)	N2—C4—C5—C6	32.8 (4)
C7—O2—N3—C6	−0.6 (3)	O2—N3—C6—C5	−0.1 (3)
C2—N1—C3—N2	−177.4 (2)	C7—C5—C6—N3	0.8 (3)
C2—N1—C3—S	0.7 (3)	C4—C5—C6—N3	176.1 (3)
C4—N2—C3—N1	178.5 (2)	N3—O2—C7—C5	1.2 (3)
C4—N2—C3—S	0.6 (3)	N3—O2—C7—C8	−179.9 (2)
C1—S—C3—N1	−0.9 (2)	C6—C5—C7—O2	−1.2 (3)
C1—S—C3—N2	177.2 (2)	C4—C5—C7—O2	−176.7 (2)
C3—N2—C4—O1	5.7 (4)	C6—C5—C7—C8	−179.8 (3)
C3—N2—C4—C5	−173.0 (2)	C4—C5—C7—C8	4.6 (5)
O1—C4—C5—C7	28.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.86	2.14	2.970 (3)	162
C6—H6A···O1ii	0.93	2.36	3.287 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.86	2.14	2.970 (3)	162
C6—H6A⋯O1ii	0.93	2.36	3.287 (4)	171

Symmetry codes: (i) ; (ii) .