4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl-idene]meth-yl}phenyl acetate.

The title mol-ecule, C(18)H(13)NO(4), 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 mol-ecule has a U-shaped conformation. Supra-molecular 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) inter-actions [3.370 (2) Å].

Related literature

For background to the biological activity of 1,3-oxazole and n class="Chemical">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 = 307.29

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.140

S = 1.06

2491 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014911/lh5032Isup2.hkl

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

C18H13NO4	F(000) = 640
Mr = 307.29	Dx = 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

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

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(Fo2) + (0.0834P)2 + 0.1813P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2491 reflections	Δρmax = 0.23 e Å−3
210 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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