(4Z)-4-Benzyl-idene-2-phenyl-1,3-oxazol-5(4H)-one.

In the title compound, C(17)H(13)NO(2), the benzene ring is twisted slightly out of the plane of the oxazole ring to which it is attached [dihedral angle = 7.98 (8)°]. Similarly, there is a twist [dihedral angle = 5.50 (8)°] between the oxazole and phenyl rings that are linked via the C=C bond [1.348 (2) Å]; the conformation about the latter is Z. In the crystal, the presence of C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.5259 (9) Å] link the mol-ecules into a three-dimensional architecture.

Related literature

For background to the biological activity of oxazolone derivatives, see: Fidanza & Dernoeden (1996 ▶); Khan et al. (2006 ▶); Puig et al. (2000 ▶) For the synthesis, see: Mariappan et al. (2011 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Orthorhombic,

a = 12.0827 (6) Å

b = 7.7848 (3) Å

c = 27.6527 (16) Å

V = 2601.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.974, T max = 0.983

7121 measured reflections

2990 independent reflections

2206 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 1.03

2990 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011579/hb6681sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011579/hb6681Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011579/hb6681Isup3.cml

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

C17H13NO2	F(000) = 1104
Mr = 263.28	Dx = 1.345 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2443 reflections
a = 12.0827 (6) Å	θ = 2.6–27.5°
b = 7.7848 (3) Å	µ = 0.09 mm−1
c = 27.6527 (16) Å	T = 100 K
V = 2601.1 (2) Å3	Polyhedron, yellow
Z = 8	0.30 × 0.25 × 0.20 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2990 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2206 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −15→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −7→10
Tmin = 0.974, Tmax = 0.983	l = −36→20
7121 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.043P)2 + 0.6059P] where P = (Fo2 + 2Fc2)/3
2990 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.70006 (8)	0.51990 (13)	0.55832 (4)	0.0199 (3)
O2	0.76383 (9)	0.68781 (14)	0.61933 (4)	0.0270 (3)
N1	0.53733 (10)	0.42459 (15)	0.58986 (4)	0.0174 (3)
C1	0.60411 (12)	0.42309 (18)	0.55339 (6)	0.0176 (3)
C2	0.69316 (13)	0.59344 (19)	0.60408 (6)	0.0197 (3)
C3	0.58820 (12)	0.52949 (18)	0.62455 (6)	0.0176 (3)
C4	0.55689 (12)	0.56871 (18)	0.67001 (6)	0.0186 (3)
H4	0.6050	0.6445	0.6868	0.022*
C5	0.46027 (12)	0.51218 (18)	0.69718 (6)	0.0176 (3)
C6	0.44944 (13)	0.5668 (2)	0.74539 (6)	0.0220 (4)
H6	0.5037	0.6409	0.7590	0.026*
C7	0.36046 (14)	0.51376 (19)	0.77344 (6)	0.0238 (4)
H7	0.3538	0.5520	0.8059	0.029*
C8	0.28135 (14)	0.40496 (19)	0.75395 (6)	0.0233 (4)
H8	0.2205	0.3683	0.7731	0.028*
C9	0.29095 (13)	0.3493 (2)	0.70625 (6)	0.0226 (4)
H9	0.2368	0.2741	0.6931	0.027*
C10	0.37888 (12)	0.40289 (19)	0.67789 (6)	0.0200 (3)
H10	0.3842	0.3656	0.6453	0.024*
C11	0.59187 (12)	0.32991 (18)	0.50822 (5)	0.0169 (3)
C12	0.67737 (13)	0.3232 (2)	0.47430 (6)	0.0221 (4)
H12	0.7441	0.3847	0.4799	0.027*
C13	0.66513 (13)	0.2269 (2)	0.43248 (6)	0.0249 (4)
H13	0.7241	0.2222	0.4098	0.030*
C14	0.56739 (13)	0.13662 (19)	0.42313 (6)	0.0216 (3)
C15	0.48133 (13)	0.14847 (19)	0.45658 (6)	0.0211 (3)
H15	0.4136	0.0906	0.4504	0.025*
C16	0.49287 (12)	0.24313 (18)	0.49867 (6)	0.0195 (3)
H16	0.4335	0.2491	0.5211	0.023*
C17	0.55537 (15)	0.0289 (2)	0.37818 (6)	0.0292 (4)
H17A	0.5060	−0.0682	0.3848	0.044*
H17B	0.6282	−0.0144	0.3684	0.044*
H17C	0.5241	0.0990	0.3521	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0168 (5)	0.0235 (5)	0.0194 (6)	−0.0029 (4)	−0.0007 (4)	0.0022 (5)
O2	0.0260 (6)	0.0308 (6)	0.0242 (6)	−0.0105 (5)	−0.0044 (5)	0.0035 (5)
N1	0.0182 (6)	0.0171 (6)	0.0168 (7)	0.0012 (5)	−0.0021 (5)	0.0014 (5)
C1	0.0160 (7)	0.0164 (7)	0.0204 (8)	0.0007 (6)	−0.0025 (6)	0.0053 (6)
C2	0.0216 (8)	0.0197 (7)	0.0176 (8)	−0.0005 (7)	−0.0043 (6)	0.0046 (6)
C3	0.0181 (7)	0.0154 (7)	0.0193 (8)	−0.0001 (6)	−0.0042 (6)	0.0030 (6)
C4	0.0189 (7)	0.0167 (7)	0.0201 (8)	0.0004 (6)	−0.0050 (6)	0.0000 (6)
C5	0.0197 (7)	0.0149 (7)	0.0182 (8)	0.0029 (6)	−0.0014 (6)	0.0019 (6)
C6	0.0249 (8)	0.0205 (7)	0.0207 (8)	0.0017 (7)	−0.0030 (7)	−0.0012 (7)
C7	0.0315 (9)	0.0230 (8)	0.0167 (8)	0.0075 (7)	0.0003 (7)	0.0002 (7)
C8	0.0242 (8)	0.0223 (8)	0.0232 (9)	0.0035 (7)	0.0051 (7)	0.0045 (7)
C9	0.0225 (8)	0.0201 (8)	0.0251 (9)	−0.0020 (7)	0.0002 (7)	−0.0004 (7)
C10	0.0214 (8)	0.0202 (7)	0.0184 (8)	0.0012 (6)	−0.0004 (6)	−0.0010 (6)
C11	0.0181 (7)	0.0166 (7)	0.0159 (8)	0.0037 (6)	−0.0004 (6)	0.0032 (6)
C12	0.0192 (7)	0.0249 (8)	0.0222 (9)	0.0008 (7)	0.0001 (7)	0.0015 (7)
C13	0.0250 (8)	0.0293 (8)	0.0203 (9)	0.0052 (7)	0.0049 (7)	0.0001 (7)
C14	0.0294 (8)	0.0164 (7)	0.0189 (8)	0.0036 (7)	−0.0019 (7)	0.0030 (6)
C15	0.0230 (8)	0.0180 (7)	0.0225 (8)	−0.0012 (6)	−0.0030 (7)	0.0028 (6)
C16	0.0199 (8)	0.0185 (7)	0.0202 (8)	0.0013 (7)	0.0006 (6)	0.0044 (6)
C17	0.0386 (10)	0.0238 (8)	0.0253 (9)	0.0016 (8)	−0.0009 (8)	−0.0033 (7)

O1—C2	1.3913 (19)	C9—C10	1.385 (2)
O1—C1	1.3895 (18)	C9—H9	0.9500
O2—C2	1.2028 (18)	C10—H10	0.9500
N1—C1	1.2915 (19)	C11—C12	1.396 (2)
N1—C3	1.4017 (19)	C11—C16	1.399 (2)
C1—C11	1.452 (2)	C12—C13	1.386 (2)
C2—C3	1.475 (2)	C12—H12	0.9500
C3—C4	1.348 (2)	C13—C14	1.399 (2)
C4—C5	1.456 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.395 (2)
C5—C10	1.406 (2)	C14—C17	1.507 (2)
C5—C6	1.405 (2)	C15—C16	1.385 (2)
C6—C7	1.388 (2)	C15—H15	0.9500
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.386 (2)	C17—H17A	0.9800
C7—H7	0.9500	C17—H17B	0.9800
C8—C9	1.393 (2)	C17—H17C	0.9800
C8—H8	0.9500
C2—O1—C1	105.22 (11)	C8—C9—H9	119.8
C1—N1—C3	105.41 (12)	C9—C10—C5	120.29 (15)
N1—C1—O1	116.08 (13)	C9—C10—H10	119.9
N1—C1—C11	127.78 (14)	C5—C10—H10	119.9
O1—C1—C11	116.13 (13)	C12—C11—C16	119.18 (14)
O2—C2—O1	121.84 (14)	C12—C11—C1	121.42 (14)
O2—C2—C3	133.00 (15)	C16—C11—C1	119.39 (13)
O1—C2—C3	105.16 (12)	C13—C12—C11	120.13 (15)
C4—C3—N1	130.33 (14)	C13—C12—H12	119.9
C4—C3—C2	121.51 (14)	C11—C12—H12	119.9
N1—C3—C2	108.12 (13)	C12—C13—C14	121.08 (15)
C3—C4—C5	129.62 (14)	C12—C13—H13	119.5
C3—C4—H4	115.2	C14—C13—H13	119.5
C5—C4—H4	115.2	C15—C14—C13	118.27 (15)
C10—C5—C6	118.55 (14)	C15—C14—C17	120.80 (15)
C10—C5—C4	123.23 (14)	C13—C14—C17	120.93 (15)
C6—C5—C4	118.21 (14)	C16—C15—C14	121.17 (15)
C7—C6—C5	120.80 (15)	C16—C15—H15	119.4
C7—C6—H6	119.6	C14—C15—H15	119.4
C5—C6—H6	119.6	C15—C16—C11	120.13 (14)
C8—C7—C6	119.90 (15)	C15—C16—H16	119.9
C8—C7—H7	120.1	C11—C16—H16	119.9
C6—C7—H7	120.1	C14—C17—H17A	109.5
C7—C8—C9	120.05 (15)	C14—C17—H17B	109.5
C7—C8—H8	120.0	H17A—C17—H17B	109.5
C9—C8—H8	120.0	C14—C17—H17C	109.5
C10—C9—C8	120.41 (15)	H17A—C17—H17C	109.5
C10—C9—H9	119.8	H17B—C17—H17C	109.5
C3—N1—C1—O1	−0.47 (16)	C6—C7—C8—C9	−0.2 (2)
C3—N1—C1—C11	178.31 (14)	C7—C8—C9—C10	−0.4 (2)
C2—O1—C1—N1	−0.24 (16)	C8—C9—C10—C5	0.9 (2)
C2—O1—C1—C11	−179.16 (12)	C6—C5—C10—C9	−0.7 (2)
C1—O1—C2—O2	−179.03 (14)	C4—C5—C10—C9	177.79 (14)
C1—O1—C2—C3	0.80 (14)	N1—C1—C11—C12	−171.85 (15)
C1—N1—C3—C4	−176.66 (15)	O1—C1—C11—C12	6.9 (2)
C1—N1—C3—C2	0.95 (15)	N1—C1—C11—C16	7.3 (2)
O2—C2—C3—C4	−3.4 (3)	O1—C1—C11—C16	−173.88 (12)
O1—C2—C3—C4	176.76 (13)	C16—C11—C12—C13	−2.1 (2)
O2—C2—C3—N1	178.70 (16)	C1—C11—C12—C13	177.12 (14)
O1—C2—C3—N1	−1.10 (15)	C11—C12—C13—C14	0.7 (2)
N1—C3—C4—C5	0.6 (3)	C12—C13—C14—C15	1.2 (2)
C2—C3—C4—C5	−176.76 (14)	C12—C13—C14—C17	−178.58 (14)
C3—C4—C5—C10	−1.3 (2)	C13—C14—C15—C16	−1.7 (2)
C3—C4—C5—C6	177.19 (15)	C17—C14—C15—C16	178.08 (14)
C10—C5—C6—C7	0.1 (2)	C14—C15—C16—C11	0.3 (2)
C4—C5—C6—C7	−178.48 (14)	C12—C11—C16—C15	1.6 (2)
C5—C6—C7—C8	0.3 (2)	C1—C11—C16—C15	−177.63 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2i	0.95	2.56	3.463 (2)	158
C6—H6···Cg1ii	0.95	2.93	3.8311 (17)	158
C9—H9···Cg1iii	0.95	2.92	3.6532 (17)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2i	0.95	2.56	3.463 (2)	158
C6—H6⋯Cg1ii	0.95	2.93	3.8311 (17)	158
C9—H9⋯Cg1iii	0.95	2.92	3.6532 (17)	135

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