Crystal structure of 2-methyl-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one

Sharma, P.; Subbulakshmi, K.N.; Narayana, B.; Byrappa, K.; Kant, R.

doi:10.1107/S2056989015000833

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o123-o124

doi:10.1107/S2056989015000833

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Crystal structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one

Preetika Sharma,^a K. N. Subbulakshmi,^b B. Narayana,^b K. Byrappa ^c and Rajni Kant ^a ^*

^aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, D. K., Mangalore, India, and ^cMangalore University, Mansagangotri, Mangalore, India
^*Correspondence e-mail: rkant.ju@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 28 December 2014; accepted 15 January 2015; online 21 January 2015)

The asymmetric unit of the title compound, C₉H₇NO₂S, contains two crystallographically independent molecules (A and B). Both molecules are almost planar [maximum deviations = 0.047 (1) and 0.090 (1) Å, respectively, for the S atoms] with the oxazole and thiophene rings being inclined to one another by 2.65 (16)° in molecule A and by 4.55 (15)° in molecule B. In the crystal, the individual molecules 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 interactions [intercentroid distances = 3.767 (2) and 3.867 (2) Å] involving inversion-related oxazole and thiophene rings in both molecules, forming a three-dimensional structure.

Keywords: crystal structure; azlactones; 1,3-oxazol-5(4H)-one; hydrogen bonding; C—H⋯π and π–π interactions.

CCDC reference: 1043723

1. 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 ).

2. Experimental

2.1. Crystal data

C₉H₇NO₂S
M_r = 193.22
Monoclinic, P 2₁ /n
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

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.842, T_max = 1.000
7052 measured reflections
3472 independent reflections
2477 reflections with I > 2σ(I)
R_int = 0.029

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.04
3472 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thiophene ring S1A/C1A–C4A.

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
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

CCDC reference: 1043723

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015000833/su5054sup1.cif

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

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

checkCIF report

Comment top

Erlenmeyer azlactones have been used in a wide variety of reactions as precursors for biologically active peptides (Etschenberg et al., 1980; Reed & Kingston, 1986), herbicides and fungicides, pesticides, agrochemical intermediates and as drugs. The crystal structures of some 1,3-oxazol-5(4H)-one derivative viz., 2-(naphthalen-1-yl)-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5(4H)-one (Gündoğdu et al., 2011a), 2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one (Sun & Cui, 2008), 4-[(3-methoxyanilino)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one (Huang et al., 2012), (E)-4-(2,5-dimethoxybenzylidene)-2-phenyl-1,3-oxazol-5(4H)-one (Asiri & Ng, 2009) have been reported. In view of the importance of 1,3-oxazol-5(4H)-one, we report herein on the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, contains two crystallographically independent molecules (A and B), which are almost identical (Fig. 2). The molecular structure is comprised of an oxazole and a thiophene ring which are almost coplanar with a dihedral angle between the rings of 2.65 (16)° in molecule A and 4.55 (15)° in molecule B. All the bond lengths and angles of the title molecule are within normal ranges, and are close to those observed for a very similar structure, viz. 2-(naphthalen-1-yl)-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one (Gündoğdu et al., 2011b).

In the crystal, the individual molecules are linked via C—H···O hydrogen bonds forming -A-B-A-B- chains along direction [101]; Fig. 2 and Table 1. The chains are linked via C-H···π (Table 1) and π-π interactions forming a three dimensional structure [Cg1···Cg2ⁱ = 3.767 (2) A° and Cg3···Cg4ⁱⁱ = 3.886 (2) Å where Cg1, Cg2, Cg3 and Cg4 are the centroids of rings S1A/C1A-C4A, O1A/N1A/C6A-C8A, S1B/C1B-C4B and O1B/N1B/C6B-C8B, respectively, with symmetry codes: (i) -x+1, -y+1, -z and (ii) -x+1, -y+1, -z+1].

Related literature top

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 top

A mixture of acetyl glycine (2 g, 0.017 mol), thiophene-2-carbaldehyde (1.91 g, 0.017 mol), anhydrous sodium acetate (1.39 g, 0.017 mol) and acetic anhydride (5.20 g, 0.051 mol) was heated on electric plate with constant stirring. As soon as the mixture liquefied completely, the resulting solution was refluxed for 2 h. 25 ml of ethanol was added slowly to the contents of the flask and the mixture was allowed to stand overnight in a refrigerator. The solid mass that separated out was stirred with 60 ml of cold water, filtered, washed with cold water and recrystallized from carbon tetrachloride. Single crystals were grown from chloroform by the slow evaporation method (m.p.: 411-412 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures top

	Fig. 1. 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.
	Fig. 2. 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).

2-Methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one top

Crystal data top

C₉H₇NO₂S	F(000) = 800
M_r = 193.22	D_x = 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

Data collection top

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

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0531P)² + 0.4552P] where P = (F_o² + 2F_c²)/3
3472 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₉H₇NO₂S	V = 1772.3 (2) Å³
M_r = 193.22	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.2264 (11) Å	µ = 0.33 mm⁻¹
b = 9.8581 (7) Å	T = 293 K
c = 15.8735 (13) Å	0.30 × 0.20 × 0.20 mm
β = 112.129 (10)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3472 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2477 reflections with I > 2σ(I)
T_min = 0.842, T_max = 1.000	R_int = 0.029
7052 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
3472 reflections	Δρ_min = −0.34 e Å⁻³
237 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the thiophene ring S1A/C1A–C4A.

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

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the thiophene ring S1A/C1A–C4A.

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

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z.

Acknowledgements

RK acknowledges the Department of Science and Technology for the single-crystal X-ray diffractometer, sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003. KNS gratefully acknowledges the Department of Chemistry and Shri Madhwa Vadiraja Institute of Technology, Bantakal, for providing research facilities.

References

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Volume 71| Part 2| February 2015| Pages o123-o124

doi:10.1107/S2056989015000833

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-methyl-4-[(thio­phen-2-yl)methyl­­idene]-1,3-oxazol-5(4H)-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one