Crystal structure of 2-methyl-4-[(thio-phen-2-yl)methyl-idene]-1,3-oxazol-5(4H)-one.

The asymmetric unit of the title compound, C9H7NO2S, contains two crystallographically independent mol-ecules (A and B). Both mol-ecules are almost planar [maximum deviations = 0.047 (1) and 0.090 (1) Å, respectively, for the S atoms] with the oxazole and thio-phene rings being inclined to one another by 2.65 (16)° in mol-ecule A and by 4.55 (15)° in mol-ecule B. In the crystal, the individual mol-ecules are linked via C-H⋯O hydrogen bonds, forming -A-B-A-B- chains along the [10-1] direction. The chains are linked via C-H⋯π and π-π inter-actions [inter-centroid distances = 3.767 (2) and 3.867 (2) Å] involving inversion-related oxazole and thio-phene rings in both mol-ecules, forming a three-dimensional structure.

Related literature

For the different roles of 1,3-oxazol-5(4H)-one derivatives, see: Etschenberg et al. (1980 ▸); Reed & Kingston (1986 ▸). For the crystal structure of 2-(naphthalen-1-yl)-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one, see: Gündoğdu et al. (2011b ▸). For the crystal structures of some oxazole compounds, see: Gündoğdu et al. (2011a ▸); Sun & Cui (2008 ▸); Huang et al. (2012 ▸); Asiri & Ng (2009 ▸).

Experimental

Crystal data

C9H7NO2S

M = 193.22

Monoclinic,

a = 12.2264 (11) Å

b = 9.8581 (7) Å

c = 15.8735 (13) Å

β = 112.129 (10)°

V = 1772.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▸) T min = 0.842, T max = 1.000

7052 measured reflections

3472 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.04

3472 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015000833/su5054sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015000833/su5054Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015000833/su5054Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015000833/su5054fig1.tif

A view of the mol­ecular structure of the two independent mol­ecules of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 40% probability level.

Click here for additional data file.

b A B . DOI: 10.1107/S2056989015000833/su5054fig2.tif

A view along the b axis of the crystal packing of the title compound. The C—H⋯O ydrogen bonds are shown as dashed lines (see Table 1 for details; mol­ecule A blue; mol­ecule B red).

CCDC reference: 1043723

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H7NO2S	F(000) = 800
Mr = 193.22	Dx = 1.448 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2325 reflections
a = 12.2264 (11) Å	θ = 4.2–29.2°
b = 9.8581 (7) Å	µ = 0.33 mm−1
c = 15.8735 (13) Å	T = 293 K
β = 112.129 (10)°	Block, white
V = 1772.3 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3472 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 26.0°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −15→9
Tmin = 0.842, Tmax = 1.000	k = −12→10
7052 measured reflections	l = −19→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.4552P] where P = (Fo2 + 2Fc2)/3
3472 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01–02-2013 CrysAlis171. NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1A	0.74841 (6)	0.94228 (7)	0.01475 (4)	0.0500 (2)
S1B	0.40438 (6)	1.07198 (8)	0.32806 (5)	0.0541 (2)
O1B	0.38555 (17)	1.22165 (19)	0.63729 (11)	0.0545 (5)
O1A	0.45883 (16)	1.33631 (19)	0.00039 (13)	0.0563 (5)
N1A	0.57961 (19)	1.1832 (2)	−0.02547 (14)	0.0480 (5)
N1B	0.42087 (19)	1.2003 (2)	0.50804 (14)	0.0458 (5)
C5B	0.2829 (2)	1.0126 (3)	0.44127 (16)	0.0433 (6)
H5B	0.2275	0.9572	0.4513	0.052*
O2B	0.2489 (2)	1.0587 (2)	0.61918 (14)	0.0730 (7)
C4A	0.7190 (2)	0.9654 (3)	0.11220 (16)	0.0415 (6)
O2A	0.47256 (17)	1.2787 (2)	0.14163 (13)	0.0672 (6)
C5A	0.6410 (2)	1.0659 (3)	0.12201 (17)	0.0445 (6)
H5A	0.6315	1.0662	0.1774	0.053*
C6A	0.5796 (2)	1.1602 (3)	0.06201 (17)	0.0433 (6)
C4B	0.3004 (2)	0.9890 (2)	0.35782 (16)	0.0403 (6)
C7A	0.5013 (2)	1.2586 (3)	0.07877 (19)	0.0500 (7)
C3B	0.2367 (2)	0.8952 (3)	0.29012 (16)	0.0442 (6)
H3B	0.1768	0.8396	0.2930	0.053*
C8A	0.5108 (2)	1.2838 (3)	−0.05642 (18)	0.0504 (7)
C3A	0.7808 (2)	0.8734 (3)	0.17737 (17)	0.0517 (7)
H3A	0.7770	0.8694	0.2347	0.062*
C6B	0.3358 (2)	1.1033 (3)	0.50605 (16)	0.0430 (6)
C7B	0.3128 (2)	1.1171 (3)	0.59019 (18)	0.0511 (7)
C8B	0.4457 (2)	1.2636 (3)	0.58308 (18)	0.0496 (7)
C2A	0.8503 (3)	0.7863 (3)	0.1489 (2)	0.0606 (8)
H2A	0.8977	0.7184	0.1852	0.073*
C9B	0.5305 (3)	1.3745 (3)	0.6211 (2)	0.0647 (8)
H9B1	0.5995	1.3399	0.6689	0.097*
H9B2	0.4949	1.4435	0.6450	0.097*
H9B3	0.5526	1.4125	0.5741	0.097*
C1B	0.3648 (3)	0.9860 (3)	0.22912 (18)	0.0571 (7)
H1B	0.4004	0.9985	0.1872	0.068*
C2B	0.2765 (3)	0.8976 (3)	0.21714 (18)	0.0581 (7)
H2B	0.2446	0.8432	0.1658	0.070*
C1A	0.8410 (3)	0.8114 (3)	0.06350 (19)	0.0560 (7)
H1A	0.8810	0.7624	0.0340	0.067*
C9A	0.4771 (3)	1.3503 (3)	−0.1459 (2)	0.0706 (9)
H9A1	0.5186	1.3084	−0.1798	0.106*
H9A2	0.4972	1.4448	−0.1375	0.106*
H9A3	0.3936	1.3408	−0.1787	0.106*

	U11	U22	U33	U12	U13	U23
S1A	0.0587 (4)	0.0545 (4)	0.0420 (4)	0.0065 (3)	0.0249 (3)	−0.0013 (3)
S1B	0.0542 (4)	0.0596 (5)	0.0523 (4)	−0.0088 (4)	0.0244 (3)	0.0029 (3)
O1B	0.0650 (12)	0.0575 (12)	0.0457 (10)	−0.0038 (10)	0.0261 (9)	−0.0097 (9)
O1A	0.0525 (11)	0.0511 (11)	0.0619 (12)	0.0123 (10)	0.0176 (9)	−0.0031 (10)
N1A	0.0516 (13)	0.0454 (13)	0.0478 (12)	0.0037 (11)	0.0197 (10)	−0.0024 (11)
N1B	0.0505 (13)	0.0448 (12)	0.0431 (12)	−0.0026 (11)	0.0187 (10)	−0.0015 (10)
C5B	0.0453 (14)	0.0428 (14)	0.0458 (14)	−0.0010 (13)	0.0217 (12)	0.0025 (13)
O2B	0.0929 (17)	0.0800 (15)	0.0692 (13)	−0.0172 (13)	0.0566 (13)	−0.0081 (11)
C4A	0.0420 (13)	0.0436 (14)	0.0419 (13)	−0.0010 (12)	0.0190 (11)	−0.0035 (12)
O2A	0.0638 (13)	0.0782 (14)	0.0669 (13)	0.0154 (11)	0.0327 (11)	−0.0119 (11)
C5A	0.0471 (15)	0.0476 (16)	0.0429 (14)	0.0002 (13)	0.0217 (12)	−0.0041 (13)
C6A	0.0416 (14)	0.0434 (15)	0.0461 (14)	0.0008 (12)	0.0178 (11)	−0.0062 (13)
C4B	0.0417 (13)	0.0380 (14)	0.0439 (13)	0.0027 (12)	0.0191 (11)	0.0049 (12)
C7A	0.0422 (15)	0.0516 (17)	0.0550 (16)	0.0030 (13)	0.0169 (13)	−0.0084 (14)
C3B	0.0474 (15)	0.0451 (15)	0.0429 (14)	−0.0044 (13)	0.0201 (12)	−0.0036 (12)
C8A	0.0478 (15)	0.0485 (16)	0.0525 (16)	−0.0018 (14)	0.0160 (13)	−0.0062 (14)
C3A	0.0594 (17)	0.0580 (17)	0.0428 (14)	0.0134 (15)	0.0252 (13)	0.0071 (14)
C6B	0.0462 (14)	0.0445 (14)	0.0421 (13)	0.0019 (13)	0.0209 (11)	0.0018 (12)
C7B	0.0584 (17)	0.0526 (17)	0.0474 (15)	0.0049 (15)	0.0258 (14)	−0.0014 (14)
C8B	0.0521 (16)	0.0468 (16)	0.0496 (15)	0.0044 (13)	0.0189 (13)	0.0014 (13)
C2A	0.0675 (19)	0.0581 (18)	0.0624 (18)	0.0195 (16)	0.0317 (16)	0.0121 (15)
C9B	0.0684 (19)	0.0578 (19)	0.0632 (18)	−0.0108 (17)	0.0194 (16)	−0.0138 (16)
C1B	0.0615 (18)	0.071 (2)	0.0457 (15)	0.0025 (17)	0.0287 (14)	0.0065 (15)
C2B	0.0682 (19)	0.0596 (18)	0.0437 (15)	−0.0025 (16)	0.0181 (14)	−0.0075 (14)
C1A	0.0621 (17)	0.0513 (17)	0.0645 (18)	0.0108 (15)	0.0350 (15)	−0.0046 (15)
C9A	0.081 (2)	0.064 (2)	0.0627 (19)	0.0044 (18)	0.0216 (16)	0.0078 (17)

S1A—C1A	1.698 (3)	C6A—C7A	1.456 (3)
S1A—C4A	1.730 (2)	C4B—C3B	1.409 (3)
S1B—C1B	1.687 (3)	C3B—C2B	1.416 (3)
S1B—C4B	1.721 (2)	C3B—H3B	0.9300
O1B—C7B	1.383 (3)	C8A—C9A	1.475 (4)
O1B—C8B	1.389 (3)	C3A—C2A	1.397 (4)
O1A—C7A	1.385 (3)	C3A—H3A	0.9300
O1A—C8A	1.385 (3)	C6B—C7B	1.471 (3)
N1A—C8A	1.273 (3)	C8B—C9B	1.471 (4)
N1A—C6A	1.407 (3)	C2A—C1A	1.341 (4)
N1B—C8B	1.276 (3)	C2A—H2A	0.9300
N1B—C6B	1.405 (3)	C9B—H9B1	0.9600
C5B—C6B	1.332 (3)	C9B—H9B2	0.9600
C5B—C4B	1.438 (3)	C9B—H9B3	0.9600
C5B—H5B	0.9300	C1B—C2B	1.344 (4)
O2B—C7B	1.194 (3)	C1B—H1B	0.9300
C4A—C3A	1.369 (3)	C2B—H2B	0.9300
C4A—C5A	1.424 (3)	C1A—H1A	0.9300
O2A—C7A	1.193 (3)	C9A—H9A1	0.9600
C5A—C6A	1.340 (3)	C9A—H9A2	0.9600
C5A—H5A	0.9300	C9A—H9A3	0.9600
C1A—S1A—C4A	91.16 (12)	C5B—C6B—N1B	127.9 (2)
C1B—S1B—C4B	91.96 (13)	C5B—C6B—C7B	124.1 (2)
C7B—O1B—C8B	105.64 (19)	N1B—C6B—C7B	108.1 (2)
C7A—O1A—C8A	105.7 (2)	O2B—C7B—O1B	122.2 (2)
C8A—N1A—C6A	105.1 (2)	O2B—C7B—C6B	133.0 (3)
C8B—N1B—C6B	105.5 (2)	O1B—C7B—C6B	104.8 (2)
C6B—C5B—C4B	128.5 (2)	N1B—C8B—O1B	116.0 (2)
C6B—C5B—H5B	115.7	N1B—C8B—C9B	129.0 (3)
C4B—C5B—H5B	115.7	O1B—C8B—C9B	115.1 (2)
C3A—C4A—C5A	125.5 (2)	C1A—C2A—C3A	112.5 (3)
C3A—C4A—S1A	110.28 (18)	C1A—C2A—H2A	123.7
C5A—C4A—S1A	124.3 (2)	C3A—C2A—H2A	123.7
C6A—C5A—C4A	128.6 (2)	C8B—C9B—H9B1	109.5
C6A—C5A—H5A	115.7	C8B—C9B—H9B2	109.5
C4A—C5A—H5A	115.7	H9B1—C9B—H9B2	109.5
C5A—C6A—N1A	127.2 (2)	C8B—C9B—H9B3	109.5
C5A—C6A—C7A	124.3 (2)	H9B1—C9B—H9B3	109.5
N1A—C6A—C7A	108.5 (2)	H9B2—C9B—H9B3	109.5
C3B—C4B—C5B	125.3 (2)	C2B—C1B—S1B	113.0 (2)
C3B—C4B—S1B	110.85 (17)	C2B—C1B—H1B	123.5
C5B—C4B—S1B	123.87 (19)	S1B—C1B—H1B	123.5
O2A—C7A—O1A	122.1 (2)	C1B—C2B—C3B	113.6 (2)
O2A—C7A—C6A	133.2 (3)	C1B—C2B—H2B	123.2
O1A—C7A—C6A	104.7 (2)	C3B—C2B—H2B	123.2
C4B—C3B—C2B	110.6 (2)	C2A—C1A—S1A	112.9 (2)
C4B—C3B—H3B	124.7	C2A—C1A—H1A	123.6
C2B—C3B—H3B	124.7	S1A—C1A—H1A	123.6
N1A—C8A—O1A	116.0 (2)	C8A—C9A—H9A1	109.5
N1A—C8A—C9A	128.5 (3)	C8A—C9A—H9A2	109.5
O1A—C8A—C9A	115.5 (2)	H9A1—C9A—H9A2	109.5
C4A—C3A—C2A	113.1 (2)	C8A—C9A—H9A3	109.5
C4A—C3A—H3A	123.4	H9A1—C9A—H9A3	109.5
C2A—C3A—H3A	123.4	H9A2—C9A—H9A3	109.5
C1A—S1A—C4A—C3A	0.2 (2)	C7A—O1A—C8A—C9A	179.2 (2)
C1A—S1A—C4A—C5A	−179.6 (2)	C5A—C4A—C3A—C2A	179.7 (3)
C3A—C4A—C5A—C6A	178.7 (3)	S1A—C4A—C3A—C2A	0.0 (3)
S1A—C4A—C5A—C6A	−1.5 (4)	C4B—C5B—C6B—N1B	1.1 (4)
C4A—C5A—C6A—N1A	−1.2 (4)	C4B—C5B—C6B—C7B	−178.7 (2)
C4A—C5A—C6A—C7A	179.7 (3)	C8B—N1B—C6B—C5B	−179.8 (3)
C8A—N1A—C6A—C5A	−178.6 (3)	C8B—N1B—C6B—C7B	0.0 (3)
C8A—N1A—C6A—C7A	0.6 (3)	C8B—O1B—C7B—O2B	179.9 (3)
C6B—C5B—C4B—C3B	−176.6 (3)	C8B—O1B—C7B—C6B	−0.1 (3)
C6B—C5B—C4B—S1B	4.0 (4)	C5B—C6B—C7B—O2B	−0.2 (5)
C1B—S1B—C4B—C3B	0.1 (2)	N1B—C6B—C7B—O2B	180.0 (3)
C1B—S1B—C4B—C5B	179.6 (2)	C5B—C6B—C7B—O1B	179.9 (2)
C8A—O1A—C7A—O2A	−180.0 (3)	N1B—C6B—C7B—O1B	0.1 (3)
C8A—O1A—C7A—C6A	−0.1 (3)	C6B—N1B—C8B—O1B	−0.1 (3)
C5A—C6A—C7A—O2A	−1.2 (5)	C6B—N1B—C8B—C9B	179.1 (3)
N1A—C6A—C7A—O2A	179.5 (3)	C7B—O1B—C8B—N1B	0.2 (3)
C5A—C6A—C7A—O1A	178.9 (2)	C7B—O1B—C8B—C9B	−179.2 (2)
N1A—C6A—C7A—O1A	−0.3 (3)	C4A—C3A—C2A—C1A	−0.2 (4)
C5B—C4B—C3B—C2B	−179.9 (2)	C4B—S1B—C1B—C2B	0.2 (2)
S1B—C4B—C3B—C2B	−0.4 (3)	S1B—C1B—C2B—C3B	−0.4 (3)
C6A—N1A—C8A—O1A	−0.7 (3)	C4B—C3B—C2B—C1B	0.5 (3)
C6A—N1A—C8A—C9A	−179.2 (3)	C3A—C2A—C1A—S1A	0.4 (4)
C7A—O1A—C8A—N1A	0.5 (3)	C4A—S1A—C1A—C2A	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O2Bi	0.93	2.56	3.449 (3)	161
C3B—H3B···O2Aii	0.93	2.49	3.336 (3)	151
C9B—H9B2···Cg1iii	0.96	2.96	3.783 (4)	145

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the thiophene ring S1A/C1AC4A.

DHA	DH	HA	D A	DHA
C3AH3AO2B i	0.93	2.56	3.449(3)	161
C3BH3BO2A ii	0.93	2.49	3.336(3)	151
C9BH9B2Cg1iii	0.96	2.96	3.783(4)	145

Symmetry codes: (i) ; (ii) ; (iii) .