4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl­idene]meth­yl}phenyl acetate

Baldaniya, B.B.; Jotani, M.M.; Tiekink, E.R.T.

doi:10.1107/S1600536810014911

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1175

https://doi.org/10.1107/S1600536810014911

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4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl acetate

Bharat B. Baldaniya,^a Mukesh M. Jotani ^b ‡ and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, M.G. Science Institute, Navrangpura, Ahmedabad, Gujarat 380 009, India, ^bDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, India, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 April 2010; accepted 23 April 2010; online 28 April 2010)

The title molecule, C₁₈H₁₃NO₄, shows a dihedral angle between the terminal acetyl group (r.m.s. deviation = 0.0081 Å) and remaining non-H atoms (r.m.s. = 0.0734 Å) of 53.45 (7)°. The configuration about the central olefinic bond is Z and overall the molecule has a U-shaped conformation. Supramolecular chains along the b-axis direction are found in the crystal structure. These are stabilized by (C=O)⋯π(ring centroid of the 1,3-oxazole ring) interactions [3.370 (2) Å].

Related literature

For background to the biological activity of 1,3-oxazole and imidazoles, see: Williams & Fu (2010 ); Khbnadidah et al. (2003 ). For related structures, see: Sun et al. (2007 ); Jotani & Baldaniya (2008 ).

Experimental

Crystal data

C₁₈H₁₃NO₄
M_r = 307.29
Monoclinic, P 2₁ /c
a = 13.3507 (15) Å
b = 3.9443 (9) Å
c = 28.527 (5) Å
β = 98.025 (11)°
V = 1487.5 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.852, T_max = 0.997
2593 measured reflections
2491 independent reflections
1795 reflections with I > 2σ(I)
R_int = 0.054
2 standard reflections every 3600 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.140
S = 1.06
2491 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: XCAD4 (Harms & Wocadlo, 1996 ); cell refinement: XCAD4; data reduction: XCAD4; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810014911/lh5032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014911/lh5032Isup2.hkl

checkCIF report

Comment top

The 1,3-oxazole ring is known to have biological activity in its own right (Williams & Fu, 2010) and serves as a useful synthetic intermediate for the synthesis of imidazoles that are also possess a wide spectrum of biological activities, such as herbicides, fungicides, anti-bacterials, etc. (Khbnadidah et al., 2003). In continuation of structural studies of oxazole compounds (Jotani & Baldaniya, 2008), the crystal structure of title compound, (I), is described herein.

The molecule of (I) is twisted around the C3–O2 bond as seen in the C2–O2–C3–C4 torsion angle of 58.2 (3) °. This results in a dihedral angle of 53.45 (7) ° between the acetyl residue [r.m.s. deviation = 0.0081 Å] and the remaining non-hydrogen atoms [r.m.s. = 0.0734 Å]; the dihedral angle formed between the two benzene rings is 5.10 (12) °. The configuration about the C9═C10 bond [1.343 (3) Å] is Z, and as the two benzene rings are orientated to the same side of the molecule, the overall molecular conformation is U-shaped. A similar conformation was reported in a di-methoxy derivative of (I), namely 2,6-dimethoxy-4-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)- phenyl acetate (Sun et al., 2007).

The crystal packing is dominated by (C═O)···π interactions that connect molecules into a linear supramolecular chain along the b axis, Fig. 2. The parameters defining this interaction are C11═O3···ring centroid(1,3-oxazole ring)ⁱ = 3.370 (2) Å and angle = 85.11 (14) ° for i: x, 1+y, z.

Related literature top

For background to the biological activity of 1,3-oxazole and imidazoles, see: Williams & Fu (2010); Khbnadidah et al. (2003). For related structures, see: Sun et al. (2007); Jotani & Baldaniya (2008).

Experimental top

A mixture of 4-acetoxyoxy benzaldehyde (0.25 mol), benzoyl amino acetic acid (0.25 mol), acetyl acetate (0.30 mol) and anhydrous sodium acetate (0.25 mol) were taken in a 500 ml round bottom flask and heated on an electric hot plate with constant stirring. After the complete liquefaction of the mixture, the flask was transferred to a sand bath and further heated for 2.5 h. Ethanol (100 ml) was added slowly to the flask and the mixture was allowed to stand overnight. The crystalline product obtained was filtered with ice-cold alcohol and then with boiling water. The crude product was crystallised from ethanol (95%) to obtain the final product (78% yield; m.pt. 428 K). The colourless crystals were obtained by slow evaporation from an ethanol solution of (I).

Structure description top

For background to the biological activity of 1,3-oxazole and imidazoles, see: Williams & Fu (2010); Khbnadidah et al. (2003). For related structures, see: Sun et al. (2007); Jotani & Baldaniya (2008).

Computing details top

Data collection: XCAD4 (Harms & Wocadlo, 1996); cell refinement: XCAD4 (Harms & Wocadlo, 1996); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. A supramolecular chain aligned along the b axis in (I), mediated by (C═ O)···π interactions (purple dashed lines). Colour code: O, red; N, blue; C, grey; and H, green.

4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene]methyl}phenyl acetate top

Crystal data top

C₁₈H₁₃NO₄	F(000) = 640
M_r = 307.29	D_x = 1.372 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.3507 (15) Å	θ = 20.0–30.0°
b = 3.9443 (9) Å	µ = 0.81 mm⁻¹
c = 28.527 (5) Å	T = 293 K
β = 98.025 (11)°	Block, colourless
V = 1487.5 (5) Å³	0.40 × 0.20 × 0.15 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1795 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 64.9°, θ_min = 3.1°
2θ scan	h = 0→15
Absorption correction: ψ scan (North et al., 1968)	k = 0→4
T_min = 0.852, T_max = 0.997	l = −33→33
2593 measured reflections	2 standard reflections every 3600 min
2491 independent reflections	intensity decay: none

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0834P)² + 0.1813P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2491 reflections	Δρ_max = 0.23 e Å⁻³
210 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0081 (8)

Crystal data top

C₁₈H₁₃NO₄	V = 1487.5 (5) Å³
M_r = 307.29	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.3507 (15) Å	µ = 0.81 mm⁻¹
b = 3.9443 (9) Å	T = 293 K
c = 28.527 (5) Å	0.40 × 0.20 × 0.15 mm
β = 98.025 (11)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1795 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.054
T_min = 0.852, T_max = 0.997	2 standard reflections every 3600 min
2593 measured reflections	intensity decay: none
2491 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
2491 reflections	Δρ_min = −0.23 e Å⁻³
210 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.98210 (13)	−0.0744 (6)	0.36427 (7)	0.0805 (7)
O2	0.96858 (10)	−0.3277 (4)	0.43327 (5)	0.0501 (4)
O3	0.36614 (12)	0.4187 (5)	0.44993 (6)	0.0606 (5)
O4	0.32332 (10)	0.1834 (4)	0.37774 (5)	0.0466 (4)
N1	0.47109 (13)	−0.0534 (5)	0.36494 (6)	0.0430 (5)
C1	1.12156 (18)	−0.3904 (7)	0.40327 (10)	0.0628 (7)
H1A	1.1314	−0.5250	0.3763	0.094*
H1B	1.1304	−0.5297	0.4311	0.094*
H1C	1.1700	−0.2091	0.4069	0.094*
C2	1.01799 (17)	−0.2475 (7)	0.39635 (9)	0.0496 (6)
C3	0.86835 (15)	−0.2184 (6)	0.43289 (8)	0.0425 (5)
C4	0.79303 (16)	−0.3064 (6)	0.39696 (8)	0.0447 (6)
H4	0.8082	−0.4318	0.3713	0.054*
C5	0.69517 (15)	−0.2074 (6)	0.39935 (7)	0.0414 (5)
H5	0.6442	−0.2660	0.3751	0.050*
C6	0.67139 (15)	−0.0187 (6)	0.43805 (7)	0.0388 (5)
C7	0.74930 (16)	0.0581 (6)	0.47402 (8)	0.0453 (6)
H7	0.7348	0.1787	0.5003	0.054*
C8	0.84763 (16)	−0.0399 (6)	0.47180 (7)	0.0479 (6)
H8	0.8990	0.0138	0.4962	0.057*
C9	0.57088 (15)	0.1106 (6)	0.44158 (7)	0.0406 (5)
H9	0.5640	0.2187	0.4699	0.049*
C10	0.48645 (15)	0.0971 (6)	0.40999 (7)	0.0396 (5)
C11	0.39108 (16)	0.2560 (6)	0.41824 (8)	0.0435 (5)
C12	0.37851 (15)	0.0018 (6)	0.34861 (7)	0.0410 (5)
C13	0.32449 (17)	−0.1052 (6)	0.30296 (8)	0.0449 (6)
C14	0.22131 (19)	−0.0575 (7)	0.29152 (9)	0.0566 (7)
H14	0.1849	0.0484	0.3129	0.068*
C15	0.1725 (2)	−0.1672 (8)	0.24835 (10)	0.0686 (8)
H15	0.1030	−0.1381	0.2409	0.082*
C16	0.2258 (2)	−0.3186 (7)	0.21650 (9)	0.0692 (8)
H16	0.1924	−0.3929	0.1875	0.083*
C17	0.3283 (2)	−0.3612 (7)	0.22719 (9)	0.0673 (8)
H17	0.3644	−0.4603	0.2051	0.081*
C18	0.3783 (2)	−0.2584 (7)	0.27036 (8)	0.0567 (7)
H18	0.4477	−0.2913	0.2777	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0539 (11)	0.1108 (18)	0.0780 (13)	0.0078 (11)	0.0130 (9)	0.0395 (13)
O2	0.0390 (8)	0.0609 (11)	0.0510 (9)	0.0101 (7)	0.0086 (7)	0.0066 (8)
O3	0.0503 (10)	0.0774 (13)	0.0557 (10)	0.0091 (9)	0.0136 (8)	−0.0205 (10)
O4	0.0387 (8)	0.0522 (10)	0.0487 (9)	0.0046 (7)	0.0056 (6)	−0.0073 (8)
N1	0.0432 (10)	0.0431 (11)	0.0428 (10)	0.0031 (9)	0.0060 (8)	−0.0049 (9)
C1	0.0478 (14)	0.0644 (18)	0.0793 (17)	0.0082 (13)	0.0195 (12)	−0.0008 (15)
C2	0.0418 (12)	0.0538 (16)	0.0533 (13)	−0.0003 (11)	0.0075 (10)	−0.0007 (12)
C3	0.0369 (11)	0.0450 (13)	0.0460 (12)	0.0036 (10)	0.0069 (9)	0.0089 (11)
C4	0.0455 (12)	0.0452 (14)	0.0442 (12)	0.0020 (11)	0.0088 (9)	−0.0014 (11)
C5	0.0412 (11)	0.0422 (13)	0.0401 (11)	−0.0019 (10)	0.0034 (9)	−0.0006 (10)
C6	0.0407 (11)	0.0385 (13)	0.0380 (10)	−0.0005 (9)	0.0085 (9)	0.0045 (10)
C7	0.0442 (12)	0.0521 (14)	0.0400 (11)	0.0002 (11)	0.0070 (9)	−0.0052 (11)
C8	0.0397 (12)	0.0605 (16)	0.0423 (12)	−0.0009 (11)	0.0017 (9)	−0.0023 (11)
C9	0.0419 (11)	0.0411 (13)	0.0400 (11)	−0.0015 (10)	0.0096 (9)	−0.0022 (10)
C10	0.0402 (11)	0.0386 (13)	0.0410 (11)	0.0010 (10)	0.0088 (9)	−0.0017 (10)
C11	0.0410 (11)	0.0472 (14)	0.0430 (11)	−0.0009 (10)	0.0078 (9)	−0.0021 (11)
C12	0.0420 (12)	0.0377 (12)	0.0441 (11)	0.0013 (10)	0.0088 (9)	−0.0023 (10)
C13	0.0534 (13)	0.0385 (13)	0.0414 (11)	−0.0013 (10)	0.0019 (9)	0.0027 (10)
C14	0.0571 (15)	0.0563 (16)	0.0531 (14)	0.0004 (12)	−0.0033 (11)	0.0013 (13)
C15	0.0656 (16)	0.0642 (19)	0.0689 (17)	−0.0058 (15)	−0.0158 (14)	0.0039 (15)
C16	0.100 (2)	0.0493 (17)	0.0513 (15)	−0.0104 (16)	−0.0120 (15)	−0.0002 (13)
C17	0.095 (2)	0.0578 (18)	0.0476 (14)	0.0008 (15)	0.0035 (14)	−0.0093 (13)
C18	0.0656 (16)	0.0528 (16)	0.0512 (14)	0.0007 (13)	0.0065 (11)	−0.0057 (12)

Geometric parameters (Å, º) top

O1—C2	1.188 (3)	C6—C9	1.452 (3)
O2—C2	1.356 (3)	C7—C8	1.378 (3)
O2—C3	1.404 (2)	C7—H7	0.9300
O3—C11	1.193 (3)	C8—H8	0.9300
O4—C12	1.385 (2)	C9—C10	1.343 (3)
O4—C11	1.394 (3)	C9—H9	0.9300
N1—C12	1.277 (3)	C10—C11	1.468 (3)
N1—C10	1.404 (3)	C12—C13	1.460 (3)
C1—C2	1.481 (3)	C13—C14	1.384 (3)
C1—H1A	0.9600	C13—C18	1.390 (3)
C1—H1B	0.9600	C14—C15	1.380 (4)
C1—H1C	0.9600	C14—H14	0.9300
C3—C8	1.375 (3)	C15—C16	1.367 (4)
C3—C4	1.376 (3)	C15—H15	0.9300
C4—C5	1.374 (3)	C16—C17	1.371 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.404 (3)	C17—C18	1.377 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.389 (3)	C18—H18	0.9300

C2—O2—C3	119.26 (17)	C10—C9—C6	129.6 (2)
C12—O4—C11	105.40 (16)	C10—C9—H9	115.2
C12—N1—C10	105.77 (17)	C6—C9—H9	115.2
C2—C1—H1A	109.5	C9—C10—N1	129.26 (19)
C2—C1—H1B	109.5	C9—C10—C11	122.8 (2)
H1A—C1—H1B	109.5	N1—C10—C11	107.96 (18)
C2—C1—H1C	109.5	O3—C11—O4	121.40 (19)
H1A—C1—H1C	109.5	O3—C11—C10	133.7 (2)
H1B—C1—H1C	109.5	O4—C11—C10	104.85 (18)
O1—C2—O2	123.0 (2)	N1—C12—O4	115.99 (18)
O1—C2—C1	126.2 (2)	N1—C12—C13	127.46 (19)
O2—C2—C1	110.7 (2)	O4—C12—C13	116.54 (18)
C8—C3—C4	121.5 (2)	C14—C13—C18	119.5 (2)
C8—C3—O2	116.73 (19)	C14—C13—C12	121.5 (2)
C4—C3—O2	121.6 (2)	C18—C13—C12	119.0 (2)
C5—C4—C3	119.5 (2)	C15—C14—C13	119.9 (3)
C5—C4—H4	120.3	C15—C14—H14	120.1
C3—C4—H4	120.3	C13—C14—H14	120.1
C4—C5—C6	120.7 (2)	C16—C15—C14	120.3 (3)
C4—C5—H5	119.7	C16—C15—H15	119.8
C6—C5—H5	119.7	C14—C15—H15	119.8
C7—C6—C5	117.93 (19)	C15—C16—C17	120.1 (2)
C7—C6—C9	118.43 (19)	C15—C16—H16	119.9
C5—C6—C9	123.59 (19)	C17—C16—H16	119.9
C8—C7—C6	121.6 (2)	C16—C17—C18	120.5 (3)
C8—C7—H7	119.2	C16—C17—H17	119.8
C6—C7—H7	119.2	C18—C17—H17	119.8
C3—C8—C7	118.7 (2)	C17—C18—C13	119.7 (3)
C3—C8—H8	120.6	C17—C18—H18	120.2
C7—C8—H8	120.6	C13—C18—H18	120.2

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃NO₄
M_r	307.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.3507 (15), 3.9443 (9), 28.527 (5)
β (°)	98.025 (11)
V (Å³)	1487.5 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.40 × 0.20 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.852, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	2593, 2491, 1795
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.140, 1.06
No. of reflections	2491
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Footnotes

‡Additional correspondence author, e-mail: mmjotani@rediffmail.com.

Acknowledgements

The authors are thankful to the Department of Science and Technology (DST), and the SAIF, I.I.T. Madras, Chennai, India, for the X-ray data collection. MMJ is grateful to the University Grant Commission (Western Regional Office), India, for a Minor Research Project F. No.47-254/07.

References

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