4-(2-Methoxy-benzyl-idene)-2-phenyl-1,3-oxazol-5(4H)-one.

The title mol-ecule, C(17)H(13)NO(3), adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is almost coplanar with the plane of the oxazolone ring system, making a dihedral angle of 2.03 (11)°. The crystal structure is stabilized by π-π inter-actions between the oxazolone ring and phenyl ring of a neighbouring mol-ecule [centroid-centroid distance = 3.550 (3)Å], and by two weak inter-molecular C-H⋯π inter-actions. In addition, the crystal structure exhibits one weak intra-molecular C-H⋯N hydrogen bond.

Related literature

For general background to azalactones and their biological and pharmaceutical properties, see: Cannella et al. (1996 ▶); Cavelier & Verducci (1995 ▶); Gelmi et al. (1997 ▶); Gonzalez-Martinez, Puchades, Maquieira, Ferrer, Marco & Barcelo (1999 ▶); Gottwald & Seebach (1999 ▶); Mesaik et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H13NO3

M = 279.28

Triclinic,

a = 8.8073 (6) Å

b = 9.6140 (6) Å

c = 9.8272 (6) Å

α = 66.503 (4)°

β = 67.248 (4)°

γ = 71.734 (4)°

V = 691.14 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.08 × 0.05 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: none

14582 measured reflections

3457 independent reflections

1464 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 0.93

3457 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010216/lx2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010216/lx2096Isup2.hkl

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

C17H13NO3	Z = 2
Mr = 279.28	F(000) = 292
Triclinic, P1	Dx = 1.342 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8073 (6) Å	Cell parameters from 1969 reflections
b = 9.6140 (6) Å	θ = 2.4–22.4°
c = 9.8272 (6) Å	µ = 0.09 mm−1
α = 66.503 (4)°	T = 296 K
β = 67.248 (4)°	Prism, yellow
γ = 71.734 (4)°	0.28 × 0.08 × 0.05 mm
V = 691.14 (8) Å3

Bruker Kappa APEXII CCD diffractometer	1464 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.048
graphite	θmax = 28.5°, θmin = 2.4°
Detector resolution: 10.0 pixels mm-1	h = −11→11
φ and ω scans	k = −12→12
14582 measured reflections	l = −13→13
3457 independent reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
3457 reflections	Δρmax = 0.16 e Å−3
192 parameters	Δρmin = −0.13 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: 0.008 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.25166 (15)	0.44719 (14)	0.39300 (14)	0.0569 (5)
O2	0.21889 (18)	0.24891 (17)	0.34504 (18)	0.0822 (6)
O3	0.71016 (18)	0.05676 (17)	−0.02406 (16)	0.0758 (6)
N1	0.51111 (18)	0.48138 (17)	0.23057 (16)	0.0496 (6)
C1	0.7332 (2)	0.2733 (2)	0.0149 (2)	0.0506 (7)
C2	0.8036 (2)	0.1640 (2)	−0.0653 (2)	0.0585 (8)
C3	0.9578 (3)	0.1700 (3)	−0.1783 (2)	0.0728 (9)
C4	1.0418 (3)	0.2832 (3)	−0.2108 (3)	0.0812 (9)
C5	0.9784 (3)	0.3890 (3)	−0.1317 (2)	0.0741 (9)
C6	0.8245 (3)	0.3836 (2)	−0.0200 (2)	0.0613 (8)
C7	0.5675 (2)	0.2690 (2)	0.1242 (2)	0.0534 (7)
C8	0.4736 (2)	0.3592 (2)	0.2139 (2)	0.0494 (7)
C9	0.3054 (3)	0.3362 (2)	0.3179 (2)	0.0570 (8)
C10	0.3815 (2)	0.5263 (2)	0.3330 (2)	0.0469 (6)
C11	0.3562 (2)	0.6487 (2)	0.3944 (2)	0.0496 (7)
C12	0.2070 (3)	0.6867 (2)	0.5026 (2)	0.0623 (8)
C13	0.1867 (3)	0.8024 (3)	0.5607 (3)	0.0762 (9)
C14	0.3129 (4)	0.8808 (3)	0.5107 (3)	0.0779 (10)
C15	0.4617 (3)	0.8459 (3)	0.4015 (3)	0.0760 (10)
C16	0.4826 (3)	0.7300 (2)	0.3435 (2)	0.0627 (8)
C17	0.7702 (3)	−0.0552 (3)	−0.1038 (3)	0.0876 (10)
H3	1.00400	0.09810	−0.23150	0.0870*
H4	1.14440	0.28850	−0.28830	0.0970*
H5	1.03870	0.46320	−0.15340	0.0890*
H6	0.78080	0.45550	0.03320	0.0740*
H7	0.51770	0.19180	0.13430	0.0640*
H12	0.12020	0.63380	0.53610	0.0750*
H13	0.08670	0.82700	0.63400	0.0910*
H14	0.29880	0.95860	0.55060	0.0940*
H15	0.54730	0.90020	0.36740	0.0910*
H16	0.58250	0.70640	0.26970	0.0750*
H17A	0.78080	−0.00370	−0.21230	0.1310*
H17B	0.69250	−0.12400	−0.06060	0.1310*
H17C	0.87760	−0.11310	−0.09190	0.1310*

	U11	U22	U33	U12	U13	U23
O1	0.0465 (8)	0.0591 (8)	0.0597 (8)	−0.0112 (7)	−0.0015 (6)	−0.0266 (7)
O2	0.0612 (10)	0.0754 (11)	0.1086 (12)	−0.0262 (9)	0.0020 (8)	−0.0443 (9)
O3	0.0732 (10)	0.0836 (11)	0.0839 (10)	−0.0087 (9)	−0.0127 (8)	−0.0548 (9)
N1	0.0455 (10)	0.0547 (10)	0.0470 (9)	−0.0084 (8)	−0.0074 (8)	−0.0216 (8)
C1	0.0443 (12)	0.0614 (13)	0.0448 (10)	−0.0030 (10)	−0.0130 (9)	−0.0211 (10)
C2	0.0491 (13)	0.0736 (15)	0.0529 (12)	0.0025 (11)	−0.0192 (10)	−0.0271 (11)
C3	0.0546 (14)	0.1005 (19)	0.0614 (13)	0.0044 (14)	−0.0130 (11)	−0.0424 (13)
C4	0.0519 (14)	0.116 (2)	0.0599 (14)	−0.0092 (15)	−0.0056 (11)	−0.0282 (15)
C5	0.0538 (14)	0.0970 (18)	0.0667 (14)	−0.0201 (13)	−0.0109 (12)	−0.0236 (13)
C6	0.0533 (13)	0.0743 (15)	0.0558 (12)	−0.0103 (12)	−0.0134 (10)	−0.0243 (11)
C7	0.0508 (12)	0.0569 (13)	0.0542 (11)	−0.0078 (10)	−0.0138 (10)	−0.0230 (10)
C8	0.0442 (12)	0.0517 (12)	0.0486 (11)	−0.0064 (10)	−0.0102 (9)	−0.0179 (10)
C9	0.0504 (13)	0.0538 (13)	0.0639 (13)	−0.0091 (11)	−0.0088 (10)	−0.0244 (11)
C10	0.0417 (11)	0.0501 (12)	0.0449 (10)	−0.0090 (10)	−0.0112 (9)	−0.0126 (9)
C11	0.0476 (12)	0.0492 (12)	0.0504 (11)	−0.0018 (10)	−0.0184 (9)	−0.0162 (10)
C12	0.0587 (14)	0.0646 (14)	0.0605 (12)	−0.0086 (11)	−0.0091 (10)	−0.0275 (11)
C13	0.0818 (18)	0.0753 (16)	0.0744 (15)	−0.0038 (14)	−0.0150 (13)	−0.0430 (13)
C14	0.100 (2)	0.0622 (15)	0.0858 (17)	0.0001 (15)	−0.0409 (15)	−0.0367 (13)
C15	0.0810 (18)	0.0670 (15)	0.0942 (18)	−0.0148 (13)	−0.0392 (15)	−0.0266 (14)
C16	0.0569 (14)	0.0641 (14)	0.0705 (13)	−0.0072 (11)	−0.0207 (11)	−0.0264 (12)
C17	0.107 (2)	0.0841 (17)	0.0864 (16)	0.0101 (15)	−0.0377 (15)	−0.0545 (15)

O1—C9	1.396 (2)	C11—C16	1.380 (3)
O1—C10	1.378 (2)	C12—C13	1.378 (3)
O2—C9	1.192 (3)	C13—C14	1.361 (5)
O3—C2	1.358 (3)	C14—C15	1.380 (4)
O3—C17	1.431 (3)	C15—C16	1.377 (3)
N1—C8	1.398 (3)	C3—H3	0.9300
N1—C10	1.285 (2)	C4—H4	0.9300
C1—C2	1.409 (3)	C5—H5	0.9300
C1—C6	1.386 (3)	C6—H6	0.9300
C1—C7	1.441 (3)	C7—H7	0.9300
C2—C3	1.383 (3)	C12—H12	0.9300
C3—C4	1.371 (4)	C13—H13	0.9300
C4—C5	1.375 (4)	C14—H14	0.9300
C5—C6	1.376 (3)	C15—H15	0.9300
C7—C8	1.345 (3)	C16—H16	0.9300
C8—C9	1.464 (3)	C17—H17A	0.9600
C10—C11	1.448 (3)	C17—H17B	0.9600
C11—C12	1.385 (3)	C17—H17C	0.9600
O1···N1	2.260 (2)	C4···H17Cvii	3.0100
O2···C14i	3.236 (3)	C5···H17Cvii	2.9800
O2···C12ii	3.411 (3)	C8···H6	2.8100
O1···H4iii	2.8000	C14···H17Aiv	3.0300
O1···H12	2.4500	C15···H17Aiv	3.0200
O2···H7	2.7000	C16···H4viii	3.0700
O2···H14i	2.7800	C17···H3	2.5300
O2···H12ii	2.7900	H3···C17	2.5300
O2···H13ii	2.9200	H3···H17A	2.3700
O3···H7	2.2700	H3···H17C	2.2900
N1···O1	2.260 (2)	H4···O1ix	2.8000
N1···C6	3.087 (3)	H4···C16viii	3.0700
N1···H6	2.4300	H4···H16viii	2.5000
N1···H16	2.6300	H6···N1	2.4300
C1···C10iv	3.553 (3)	H6···C8	2.8100
C2···C10iv	3.532 (3)	H7···O2	2.7000
C5···C9iv	3.481 (4)	H7···O3	2.2700
C6···N1	3.087 (3)	H7···H17Bx	2.5600
C6···C9iv	3.392 (3)	H12···O1	2.4500
C6···C8iv	3.561 (3)	H12···O2ii	2.7900
C8···C14v	3.524 (4)	H13···O2ii	2.9200
C8···C6iv	3.561 (3)	H14···O2vi	2.7800
C9···C5iv	3.481 (4)	H16···N1	2.6300
C9···C6iv	3.392 (3)	H16···H4viii	2.5000
C10···C16v	3.530 (3)	H17A···C3	2.7900
C10···C2iv	3.532 (3)	H17A···H3	2.3700
C10···C1iv	3.553 (3)	H17A···C14iv	3.0300
C12···O2ii	3.411 (3)	H17A···C15iv	3.0200
C14···C8v	3.524 (4)	H17B···H7x	2.5600
C14···O2vi	3.236 (3)	H17C···C3	2.7400
C16···C10v	3.530 (3)	H17C···H3	2.2900
C3···H17A	2.7900	H17C···C4vii	3.0100
C3···H17C	2.7400	H17C···C5vii	2.9800
C9—O1—C10	105.44 (16)	C14—C15—C16	119.5 (3)
C2—O3—C17	119.06 (18)	C11—C16—C15	120.4 (2)
C8—N1—C10	105.35 (16)	C2—C3—H3	120.00
C2—C1—C6	118.16 (17)	C4—C3—H3	120.00
C2—C1—C7	118.56 (17)	C3—C4—H4	119.00
C6—C1—C7	123.23 (18)	C5—C4—H4	119.00
O3—C2—C1	115.60 (17)	C4—C5—H5	120.00
O3—C2—C3	123.94 (19)	C6—C5—H5	120.00
C1—C2—C3	120.5 (2)	C1—C6—H6	119.00
C2—C3—C4	119.2 (2)	C5—C6—H6	119.00
C3—C4—C5	121.7 (3)	C1—C7—H7	115.00
C4—C5—C6	119.1 (3)	C8—C7—H7	115.00
C1—C6—C5	121.38 (19)	C11—C12—H12	120.00
C1—C7—C8	130.09 (18)	C13—C12—H12	120.00
N1—C8—C7	129.85 (18)	C12—C13—H13	120.00
N1—C8—C9	108.50 (16)	C14—C13—H13	120.00
C7—C8—C9	121.64 (18)	C13—C14—H14	120.00
O1—C9—O2	121.5 (2)	C15—C14—H14	120.00
O1—C9—C8	104.65 (18)	C14—C15—H15	120.00
O2—C9—C8	133.90 (18)	C16—C15—H15	120.00
O1—C10—N1	116.07 (17)	C11—C16—H16	120.00
O1—C10—C11	116.07 (16)	C15—C16—H16	120.00
N1—C10—C11	127.85 (18)	O3—C17—H17A	110.00
C10—C11—C12	121.32 (19)	O3—C17—H17B	109.00
C10—C11—C16	119.45 (17)	O3—C17—H17C	109.00
C12—C11—C16	119.23 (18)	H17A—C17—H17B	109.00
C11—C12—C13	120.2 (2)	H17A—C17—H17C	109.00
C12—C13—C14	120.0 (3)	H17B—C17—H17C	109.00
C13—C14—C15	120.6 (3)
C10—O1—C9—O2	−179.7 (2)	C3—C4—C5—C6	−1.8 (4)
C10—O1—C9—C8	0.43 (19)	C4—C5—C6—C1	0.5 (4)
C9—O1—C10—N1	−0.3 (2)	C1—C7—C8—N1	−2.0 (3)
C9—O1—C10—C11	−179.54 (16)	C1—C7—C8—C9	179.55 (19)
C17—O3—C2—C1	177.88 (19)	N1—C8—C9—O1	−0.5 (2)
C17—O3—C2—C3	−1.9 (3)	N1—C8—C9—O2	179.7 (2)
C10—N1—C8—C7	−178.4 (2)	C7—C8—C9—O1	178.32 (17)
C10—N1—C8—C9	0.3 (2)	C7—C8—C9—O2	−1.5 (4)
C8—N1—C10—O1	0.0 (2)	O1—C10—C11—C12	−2.4 (3)
C8—N1—C10—C11	179.13 (18)	O1—C10—C11—C16	178.04 (17)
C6—C1—C2—O3	178.68 (18)	N1—C10—C11—C12	178.42 (19)
C6—C1—C2—C3	−1.6 (3)	N1—C10—C11—C16	−1.1 (3)
C7—C1—C2—O3	−3.8 (3)	C10—C11—C12—C13	179.2 (2)
C7—C1—C2—C3	175.91 (19)	C16—C11—C12—C13	−1.2 (3)
C2—C1—C6—C5	1.2 (3)	C10—C11—C16—C15	−179.4 (2)
C7—C1—C6—C5	−176.2 (2)	C12—C11—C16—C15	1.1 (3)
C2—C1—C7—C8	−179.85 (19)	C11—C12—C13—C14	0.6 (4)
C6—C1—C7—C8	−2.5 (3)	C12—C13—C14—C15	0.2 (4)
O3—C2—C3—C4	−180.0 (2)	C13—C14—C15—C16	−0.4 (4)
C1—C2—C3—C4	0.3 (3)	C14—C15—C16—C11	−0.3 (4)
C2—C3—C4—C5	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1	0.93	2.43	3.087 (3)	127
C17—H17A···Cg3iv	0.96	2.81	3.682 (3)	151
C17—H17C···Cg2vii	0.96	2.96	3.832 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1	0.93	2.43	3.087 (3)	127
C17—H17A⋯Cg3i	0.96	2.81	3.682 (3)	151
C17—H17C⋯Cg2ii	0.96	2.96	3.832 (3)	151

Symmetry codes: (i) ; (ii) . Cg2 is the centroid of the C1–C6 benzene ring and Cg3 is the centroid of the C11—C16 phenyl ring.