2-(Naphthalen-1-yl)-4-(naphthalen-1-yl-methyl-idene)-1,3-oxazol-5(4H)-one.

In the title compound, C(24)H(15)NO(2), the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intra-molecular C-H⋯N hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, inter-molecular weak C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. π-π contacts between the oxazole and naphthalene rings and between the naphthalene ring systems [centroid-centroid distances = 3.5947 (9) and 3.7981 (9) Å] may further stabilize the crystal structure. Three weak C-H⋯π inter-actions also occur.

Related literature

For the roles of oxazolones in the syntheses of amino acids, peptides, anti­microbial or anti­tumor compounds, immunomodulators, heterocyclic precursors for biosensors coupling and/or photosensitive composition devices for proteins, see: Gottwald & Seebach (1999 ▶); Meiwes et al. (1997 ▶); Martinez et al. (1964 ▶); Gelmi et al. (1997 ▶); Croce et al. (1994 ▶); Cannella et al. (1996 ▶); Kojima et al. (1998 ▶). For applications of the 5-oxazolones, including their use in semiconductor devices because of their promising photophysical and photochemical activity, see: Gündoğdu et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H15NO2

M = 349.37

Monoclinic,

a = 18.6927 (5) Å

b = 6.0646 (2) Å

c = 15.6262 (5) Å

β = 107.212 (2)°

V = 1692.11 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.42 × 0.35 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.964, T max = 0.986

29257 measured reflections

4260 independent reflections

2911 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.07

4260 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015340/xu5196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015340/xu5196Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015340/xu5196Isup3.cml

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

C24H15NO2	F(000) = 728
Mr = 349.37	Dx = 1.371 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3844 reflections
a = 18.6927 (5) Å	θ = 2.3–25.8°
b = 6.0646 (2) Å	µ = 0.09 mm−1
c = 15.6262 (5) Å	T = 100 K
β = 107.212 (2)°	Block, yellow
V = 1692.11 (9) Å3	0.42 × 0.35 × 0.16 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	4260 independent reflections
Radiation source: fine-focus sealed tube	2911 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 28.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −25→25
Tmin = 0.964, Tmax = 0.986	k = −8→8
29257 measured reflections	l = −20→20

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) = 0.136	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0712P)2 + 0.094P] where P = (Fo2 + 2Fc2)/3
4260 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.44739 (6)	−0.05303 (17)	1.11266 (7)	0.0226 (3)
O2	0.51969 (6)	0.2213 (2)	1.08529 (8)	0.0339 (3)
N1	0.33689 (7)	0.0161 (2)	1.00801 (8)	0.0182 (3)
C1	0.30409 (8)	0.4225 (2)	0.88040 (10)	0.0183 (3)
C2	0.24089 (8)	0.2914 (2)	0.85707 (10)	0.0183 (3)
H2	0.2421	0.1521	0.8852	0.022*
C3	0.17453 (8)	0.3596 (2)	0.79239 (10)	0.0185 (3)
C4	0.11021 (9)	0.2236 (3)	0.76755 (11)	0.0231 (4)
H4	0.1109	0.0848	0.7960	0.028*
C5	0.04717 (9)	0.2900 (3)	0.70303 (11)	0.0263 (4)
H5	0.0044	0.1969	0.6866	0.032*
C6	0.04523 (9)	0.4962 (3)	0.66073 (11)	0.0265 (4)
H6	0.0012	0.5407	0.6156	0.032*
C7	0.10607 (9)	0.6326 (3)	0.68407 (10)	0.0230 (4)
H7	0.1038	0.7716	0.6554	0.028*
C8	0.17232 (8)	0.5692 (2)	0.75047 (10)	0.0188 (3)
C9	0.23747 (9)	0.7022 (2)	0.77577 (10)	0.0208 (3)
H9	0.2368	0.8431	0.7490	0.025*
C10	0.30132 (9)	0.6317 (2)	0.83806 (10)	0.0200 (3)
H10	0.3444	0.7234	0.8533	0.024*
C11	0.37403 (8)	0.3572 (2)	0.94585 (10)	0.0197 (3)
H11	0.4156	0.4516	0.9508	0.024*
C12	0.38719 (8)	0.1798 (2)	1.00029 (10)	0.0191 (3)
C13	0.45933 (9)	0.1340 (3)	1.06678 (11)	0.0227 (4)
C14	0.37283 (8)	−0.1109 (2)	1.07250 (10)	0.0175 (3)
C15	0.34675 (8)	−0.3067 (2)	1.10825 (10)	0.0179 (3)
C16	0.39709 (9)	−0.4187 (3)	1.17708 (10)	0.0217 (3)
H16	0.4460	−0.3605	1.2022	0.026*
C17	0.37753 (9)	−0.6171 (3)	1.21081 (10)	0.0229 (4)
H17	0.4126	−0.6898	1.2592	0.027*
C18	0.30808 (9)	−0.7050 (2)	1.17389 (10)	0.0212 (3)
H18	0.2961	−0.8434	1.1947	0.025*
C19	0.25329 (9)	−0.5932 (2)	1.10494 (10)	0.0192 (3)
C20	0.18039 (9)	−0.6812 (3)	1.07013 (10)	0.0227 (4)
H20	0.1690	−0.8202	1.0909	0.027*
C21	0.12628 (9)	−0.5699 (3)	1.00735 (11)	0.0254 (4)
H21	0.0775	−0.6308	0.9846	0.031*
C22	0.14316 (9)	−0.3641 (3)	0.97648 (11)	0.0238 (4)
H22	0.1052	−0.2854	0.9334	0.029*
C23	0.21331 (8)	−0.2757 (3)	1.00745 (10)	0.0202 (3)
H23	0.2234	−0.1371	0.9852	0.024*
C24	0.27132 (8)	−0.3873 (2)	1.07232 (10)	0.0172 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0174 (5)	0.0225 (6)	0.0250 (6)	−0.0026 (4)	0.0017 (5)	0.0044 (5)
O2	0.0192 (6)	0.0353 (7)	0.0414 (8)	−0.0083 (5)	0.0002 (5)	0.0108 (6)
N1	0.0193 (7)	0.0164 (6)	0.0190 (6)	−0.0017 (5)	0.0059 (5)	0.0001 (5)
C1	0.0221 (8)	0.0179 (7)	0.0165 (7)	−0.0010 (6)	0.0081 (6)	−0.0024 (6)
C2	0.0216 (8)	0.0164 (7)	0.0176 (8)	−0.0013 (6)	0.0070 (6)	0.0008 (6)
C3	0.0188 (8)	0.0200 (8)	0.0172 (8)	0.0012 (6)	0.0060 (6)	−0.0004 (6)
C4	0.0209 (8)	0.0236 (8)	0.0245 (8)	−0.0014 (6)	0.0064 (7)	0.0029 (7)
C5	0.0193 (8)	0.0328 (9)	0.0255 (9)	−0.0023 (7)	0.0048 (7)	0.0016 (7)
C6	0.0219 (8)	0.0315 (9)	0.0252 (9)	0.0069 (7)	0.0054 (7)	0.0023 (7)
C7	0.0260 (9)	0.0223 (8)	0.0220 (8)	0.0052 (6)	0.0091 (7)	0.0021 (6)
C8	0.0223 (8)	0.0197 (7)	0.0157 (7)	0.0018 (6)	0.0074 (6)	−0.0013 (6)
C9	0.0305 (9)	0.0147 (7)	0.0195 (8)	−0.0001 (6)	0.0110 (7)	0.0008 (6)
C10	0.0227 (8)	0.0190 (8)	0.0195 (8)	−0.0035 (6)	0.0079 (6)	−0.0023 (6)
C11	0.0195 (8)	0.0196 (7)	0.0206 (8)	−0.0041 (6)	0.0072 (6)	−0.0019 (6)
C12	0.0168 (7)	0.0205 (8)	0.0199 (8)	−0.0030 (6)	0.0053 (6)	−0.0025 (6)
C13	0.0212 (8)	0.0211 (8)	0.0248 (8)	−0.0012 (6)	0.0052 (7)	0.0028 (7)
C14	0.0147 (7)	0.0197 (7)	0.0179 (8)	−0.0009 (6)	0.0042 (6)	−0.0028 (6)
C15	0.0199 (8)	0.0186 (7)	0.0159 (7)	0.0002 (6)	0.0064 (6)	0.0001 (6)
C16	0.0198 (8)	0.0238 (8)	0.0207 (8)	0.0004 (6)	0.0047 (6)	0.0001 (6)
C17	0.0266 (9)	0.0230 (8)	0.0185 (8)	0.0041 (7)	0.0058 (7)	0.0043 (6)
C18	0.0296 (9)	0.0172 (7)	0.0192 (8)	−0.0008 (6)	0.0110 (7)	0.0017 (6)
C19	0.0242 (8)	0.0186 (7)	0.0169 (8)	−0.0003 (6)	0.0095 (6)	−0.0031 (6)
C20	0.0279 (9)	0.0201 (8)	0.0232 (8)	−0.0072 (6)	0.0123 (7)	−0.0029 (6)
C21	0.0224 (8)	0.0286 (9)	0.0255 (9)	−0.0075 (7)	0.0073 (7)	−0.0023 (7)
C22	0.0193 (8)	0.0283 (9)	0.0222 (8)	−0.0002 (6)	0.0039 (7)	0.0015 (7)
C23	0.0200 (8)	0.0202 (8)	0.0204 (8)	−0.0018 (6)	0.0061 (6)	0.0010 (6)
C24	0.0202 (8)	0.0181 (7)	0.0146 (7)	−0.0009 (6)	0.0072 (6)	−0.0019 (6)

O1—C13	1.3949 (18)	C11—C1	1.456 (2)
O1—C14	1.3935 (17)	C11—H11	0.9500
O2—C13	1.2015 (18)	C12—C11	1.348 (2)
N1—C12	1.3971 (18)	C12—C13	1.465 (2)
N1—C14	1.2880 (18)	C15—C14	1.456 (2)
C1—C2	1.380 (2)	C15—C16	1.380 (2)
C1—C10	1.424 (2)	C16—H16	0.9500
C2—C3	1.411 (2)	C17—C16	1.404 (2)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.414 (2)	C18—C17	1.364 (2)
C3—C8	1.425 (2)	C18—H18	0.9500
C4—C5	1.365 (2)	C19—C18	1.420 (2)
C4—H4	0.9500	C20—C19	1.414 (2)
C5—C6	1.410 (2)	C20—H20	0.9500
C5—H5	0.9500	C21—C20	1.361 (2)
C6—C7	1.366 (2)	C21—C22	1.407 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.366 (2)
C8—C7	1.413 (2)	C22—H22	0.9500
C9—C8	1.416 (2)	C23—C24	1.418 (2)
C9—H9	0.9500	C23—H23	0.9500
C10—C9	1.367 (2)	C24—C15	1.440 (2)
C10—H10	0.9500	C24—C19	1.426 (2)
C14—O1—C13	105.32 (11)	C11—C12—C13	123.81 (14)
C14—N1—C12	106.50 (13)	O1—C13—C12	105.36 (12)
C2—C1—C10	118.66 (14)	O2—C13—O1	121.07 (14)
C2—C1—C11	123.31 (14)	O2—C13—C12	133.56 (15)
C10—C1—C11	118.03 (13)	O1—C14—C15	115.87 (12)
C1—C2—C3	121.52 (14)	N1—C14—O1	114.99 (13)
C1—C2—H2	119.2	N1—C14—C15	129.14 (14)
C3—C2—H2	119.2	C16—C15—C14	118.16 (14)
C2—C3—C4	121.43 (14)	C16—C15—C24	119.98 (14)
C2—C3—C8	119.38 (14)	C24—C15—C14	121.84 (13)
C4—C3—C8	119.18 (14)	C15—C16—C17	121.39 (14)
C3—C4—H4	119.7	C15—C16—H16	119.3
C5—C4—C3	120.55 (15)	C17—C16—H16	119.3
C5—C4—H4	119.7	C16—C17—H17	120.1
C4—C5—C6	120.32 (15)	C18—C17—C16	119.81 (14)
C4—C5—H5	119.8	C18—C17—H17	120.1
C6—C5—H5	119.8	C17—C18—C19	121.13 (14)
C5—C6—H6	119.7	C17—C18—H18	119.4
C7—C6—C5	120.53 (15)	C19—C18—H18	119.4
C7—C6—H6	119.7	C18—C19—C24	119.71 (14)
C6—C7—C8	120.72 (15)	C20—C19—C18	120.54 (14)
C6—C7—H7	119.6	C20—C19—C24	119.73 (14)
C8—C7—H7	119.6	C19—C20—H20	119.5
C7—C8—C3	118.68 (14)	C21—C20—C19	121.06 (15)
C7—C8—C9	122.97 (14)	C21—C20—H20	119.5
C9—C8—C3	118.32 (13)	C20—C21—C22	119.51 (15)
C8—C9—H9	119.4	C20—C21—H21	120.2
C10—C9—C8	121.21 (14)	C22—C21—H21	120.2
C10—C9—H9	119.4	C21—C22—H22	119.5
C1—C10—H10	119.5	C23—C22—C21	121.06 (15)
C9—C10—C1	120.91 (14)	C23—C22—H22	119.5
C9—C10—H10	119.5	C22—C23—C24	121.11 (14)
C1—C11—H11	115.9	C22—C23—H23	119.4
C12—C11—C1	128.18 (14)	C24—C23—H23	119.4
C12—C11—H11	115.9	C19—C24—C15	117.75 (13)
N1—C12—C13	107.81 (13)	C23—C24—C15	124.75 (14)
C11—C12—N1	128.32 (14)	C23—C24—C19	117.50 (14)
C14—O1—C13—O2	−178.58 (15)	C13—C12—C11—C1	−177.33 (14)
C14—O1—C13—C12	1.12 (15)	N1—C12—C13—O1	−1.62 (16)
C13—O1—C14—N1	−0.25 (17)	N1—C12—C13—O2	178.04 (18)
C13—O1—C14—C15	179.03 (12)	C11—C12—C13—O1	175.62 (14)
C14—N1—C12—C11	−175.61 (16)	C11—C12—C13—O2	−4.7 (3)
C14—N1—C12—C13	1.47 (16)	C16—C15—C14—O1	−0.7 (2)
C12—N1—C14—O1	−0.79 (17)	C16—C15—C14—N1	178.50 (15)
C12—N1—C14—C15	−179.96 (15)	C24—C15—C14—O1	−179.11 (12)
C10—C1—C2—C3	0.4 (2)	C24—C15—C14—N1	0.1 (2)
C11—C1—C2—C3	−179.11 (13)	C14—C15—C16—C17	−175.58 (14)
C2—C1—C10—C9	0.2 (2)	C24—C15—C16—C17	2.9 (2)
C11—C1—C10—C9	179.72 (14)	C18—C17—C16—C15	1.6 (2)
C1—C2—C3—C4	178.99 (14)	C19—C18—C17—C16	−3.6 (2)
C1—C2—C3—C8	−0.4 (2)	C20—C19—C18—C17	−177.05 (14)
C2—C3—C4—C5	−178.21 (14)	C24—C19—C18—C17	1.2 (2)
C8—C3—C4—C5	1.2 (2)	C21—C20—C19—C18	176.55 (14)
C2—C3—C8—C7	178.33 (14)	C21—C20—C19—C24	−1.7 (2)
C2—C3—C8—C9	−0.1 (2)	C22—C21—C20—C19	0.1 (2)
C4—C3—C8—C7	−1.1 (2)	C20—C21—C22—C23	1.0 (2)
C4—C3—C8—C9	−179.54 (13)	C21—C22—C23—C24	−0.5 (2)
C3—C4—C5—C6	−0.5 (2)	C22—C23—C24—C15	179.71 (13)
C4—C5—C6—C7	−0.4 (2)	C22—C23—C24—C19	−1.0 (2)
C3—C8—C7—C6	0.2 (2)	C19—C24—C15—C14	173.26 (13)
C5—C6—C7—C8	0.5 (2)	C19—C24—C15—C16	−5.2 (2)
C9—C8—C7—C6	178.61 (14)	C23—C24—C15—C14	−7.5 (2)
C10—C9—C8—C3	0.7 (2)	C23—C24—C15—C16	174.11 (14)
C10—C9—C8—C7	−177.68 (14)	C15—C24—C19—C18	3.2 (2)
C1—C10—C9—C8	−0.7 (2)	C15—C24—C19—C20	−178.59 (13)
C12—C11—C1—C2	−8.0 (3)	C23—C24—C19—C18	−176.15 (13)
C12—C11—C1—C10	172.50 (15)	C23—C24—C19—C20	2.1 (2)
N1—C12—C11—C1	−0.7 (3)

Cg1, Cg2 and Cg4 are the centroids of the rings A (C1—C3/C8—C10), B (C3—C8) and D (C15—C19/C24), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.95	2.34	3.0110 (19)	127
C10—H10···O2i	0.95	2.46	3.324 (2)	152
C11—H11···O2i	0.95	2.47	3.3601 (18)	155
C23—H23···N1	0.95	2.25	2.908 (2)	126
C9—H9···Cg4ii	0.95	2.87	3.543 (2)	129
C18—H18···Cg1iii	0.95	2.61	3.381 (2)	139
C20—H20···Cg2iii	0.95	2.75	3.450 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C1—C3/C8—C10, C3—C8 and C15—C19/C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N1	0.95	2.34	3.0110 (19)	127
C10—H10⋯O2i	0.95	2.46	3.324 (2)	152
C11—H11⋯O2i	0.95	2.47	3.3601 (18)	155
C23—H23⋯N1	0.95	2.25	2.908 (2)	126
C9—H9⋯Cg4ii	0.95	2.87	3.543 (2)	129
C18—H18⋯Cg1iii	0.95	2.61	3.381 (2)	139
C20—H20⋯Cg2iii	0.95	2.75	3.450 (2)	131

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