2-(4-Methyl-phen-yl)-6-nitro-1,3-benzoxazole.

The title compound, C14H10N2O3, is a π-conjugated mol-ecule containing a benzoxazole aromatic fused heterobicycle. The benzoxazole ring system is planar within 0.01 Å. The mol-ecule assumes an approximately flat conformation, the benzoxazole ring system forming dihedral angles of 6.52 (12) and 7.4 (3)° with the benzene ring and the nitro group, respectively. In the crystal, mol-ecules are connected by very weak C-H⋯O hydrogen inter-actions, forming chains running parallel to the a or c axes. The methyl H atoms are disordered over two sets of sites of equal occupancy rotated by 60°.

Related literature

For general information on heterocycles in organic electronics and optoelectronics, see: Dalton (2002 ▶); Heeger (2010 ▶). For heterocycle-based semiconductors, optoelectronic and piezoelectric materials, see: Carella, Centore, Sirigu et al. (2004 ▶); Centore, Ricciotti et al. (2012 ▶); Centore, Concilio et al. (2012 ▶). For structural and theoretical analysis of conjugation in heterocycle-based organic mol­ecules, see: Carella, Centore, Fort et al. (2004 ▶); Gainsford et al. (2008 ▶). For structural and theoretical analysis of conjugation in heterocycle-based metallorganic compounds, see: Takjoo et al. (2011 ▶); Takjoo & Centore (2013 ▶). For theoretical computations on similar compounds, see: Capobianco et al. (2012 ▶, 2013 ▶). For the synthesis of related heterocyclic compounds, see: Bruno et al. (2002 ▶); Centore et al. (2007 ▶); Piccialli et al. (2013 ▶); Centore, Fusco, Capobianco et al. (2013 ▶). For hydrogen bonding in crystals see: Desiraju & Steiner (1999 ▶); Centore, Fusco, Jazbinsek et al. (2013 ▶).

Experimental

Crystal data

C14H10N2O3

M = 254.24

Orthorhombic,

a = 27.251 (4) Å

b = 7.4457 (6) Å

c = 11.990 (9) Å

V = 2432.8 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.40 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius MACH3 diffractometer

2968 measured reflections

2140 independent reflections

970 reflections with I > 2σ(I)

R int = 0.020

1 standard reflections every 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.168

S = 1.11

2140 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: MACH3/PC Software (Nonius, 1996 ▶); cell refinement: CELLFITW (Centore, 2004 ▶); data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008970/rz5053sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008970/rz5053Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008970/rz5053Isup3.cml

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

C14H10N2O3	F(000) = 1056
Mr = 254.24	Dx = 1.388 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 27.251 (4) Å	θ = 12.2–12.4°
b = 7.4457 (6) Å	µ = 0.10 mm−1
c = 11.990 (9) Å	T = 293 K
V = 2432.8 (19) Å3	Prism, brown
Z = 8	0.40 × 0.20 × 0.20 mm

Enraf–Nonius MACH3 diffractometer	Rint = 0.020
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.5°
Graphite monochromator	h = −12→32
non–profiled ω scans	k = −3→8
2968 measured reflections	l = −5→14
2140 independent reflections	1 standard reflections every 120 min
970 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.383P] where P = (Fo2 + 2Fc2)/3
2140 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 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.

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 > σ(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	Occ. (<1)
O1	0.05625 (9)	0.1644 (3)	0.0918 (2)	0.0545 (7)
O2	0.25311 (13)	−0.0885 (6)	0.2271 (3)	0.1125 (14)
O3	0.19587 (12)	−0.0394 (6)	0.3439 (3)	0.1144 (14)
N1	0.08562 (12)	0.1994 (4)	−0.0827 (3)	0.0614 (10)
N2	0.21215 (15)	−0.0363 (6)	0.2493 (4)	0.0771 (11)
C1	−0.14836 (14)	0.4375 (6)	−0.1283 (4)	0.0819 (15)
H1A	−0.1684	0.3329	−0.1391	0.123*	0.57 (5)
H1B	−0.1477	0.5068	−0.1958	0.123*	0.57 (5)
H1C	−0.1618	0.5090	−0.0690	0.123*	0.57 (5)
H1D	−0.1502	0.5663	−0.1302	0.123*	0.43 (5)
H1E	−0.1709	0.3923	−0.0735	0.123*	0.43 (5)
H1F	−0.1568	0.3901	−0.2002	0.123*	0.43 (5)
C2	−0.09695 (16)	0.3808 (5)	−0.0983 (4)	0.0624 (12)
C3	−0.05929 (17)	0.3930 (6)	−0.1742 (4)	0.0754 (13)
H3	−0.0656	0.4411	−0.2443	0.091*
C4	−0.01233 (16)	0.3358 (6)	−0.1496 (4)	0.0710 (13)
H4	0.0122	0.3420	−0.2035	0.085*
C5	−0.00180 (14)	0.2695 (5)	−0.0448 (3)	0.0516 (10)
C6	−0.03907 (14)	0.2611 (5)	0.0325 (3)	0.0621 (11)
H6	−0.0325	0.2182	0.1038	0.074*
C7	−0.08606 (15)	0.3154 (6)	0.0058 (4)	0.0682 (13)
H7	−0.1107	0.3075	0.0592	0.082*
C8	0.04769 (15)	0.2121 (5)	−0.0175 (3)	0.0521 (10)
C9	0.12336 (14)	0.1393 (5)	−0.0134 (3)	0.0548 (11)
C10	0.17235 (15)	0.1012 (6)	−0.0351 (4)	0.0724 (13)
H10	0.1855	0.1146	−0.1062	0.087*
C11	0.20086 (14)	0.0426 (6)	0.0532 (4)	0.0718 (13)
H11	0.2337	0.0139	0.0416	0.086*
C12	0.18069 (14)	0.0268 (6)	0.1583 (4)	0.0592 (11)
C13	0.13235 (14)	0.0639 (5)	0.1837 (3)	0.0571 (11)
H13	0.1194	0.0525	0.2551	0.069*
C14	0.10530 (14)	0.1191 (5)	0.0941 (3)	0.0509 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0553 (17)	0.0632 (18)	0.0449 (16)	0.0015 (13)	0.0038 (13)	0.0002 (14)
O2	0.057 (2)	0.171 (4)	0.110 (3)	0.020 (2)	−0.005 (2)	0.013 (3)
O3	0.086 (2)	0.190 (4)	0.068 (2)	0.022 (3)	−0.004 (2)	0.022 (3)
N1	0.064 (2)	0.073 (3)	0.0474 (19)	−0.0022 (18)	0.010 (2)	−0.0039 (19)
N2	0.058 (2)	0.096 (3)	0.077 (3)	−0.006 (2)	−0.004 (2)	0.006 (3)
C1	0.073 (3)	0.070 (3)	0.103 (4)	0.010 (3)	−0.024 (3)	−0.008 (3)
C2	0.071 (3)	0.051 (3)	0.066 (3)	0.000 (2)	−0.008 (3)	−0.011 (3)
C3	0.090 (3)	0.087 (3)	0.049 (3)	0.014 (3)	−0.011 (3)	0.007 (3)
C4	0.075 (3)	0.086 (3)	0.052 (3)	0.009 (3)	0.002 (2)	−0.001 (3)
C5	0.060 (2)	0.051 (3)	0.044 (2)	0.000 (2)	−0.002 (2)	−0.003 (2)
C6	0.064 (3)	0.073 (3)	0.050 (2)	−0.004 (3)	0.002 (2)	0.004 (2)
C7	0.060 (3)	0.078 (3)	0.067 (3)	−0.006 (2)	0.004 (2)	0.001 (3)
C8	0.067 (3)	0.051 (3)	0.038 (2)	0.000 (2)	−0.001 (2)	−0.003 (2)
C9	0.058 (3)	0.058 (3)	0.048 (2)	−0.009 (2)	0.008 (2)	−0.007 (2)
C10	0.065 (3)	0.093 (4)	0.058 (3)	−0.003 (3)	0.019 (3)	−0.001 (3)
C11	0.053 (3)	0.092 (3)	0.070 (3)	−0.001 (3)	0.010 (2)	−0.003 (3)
C12	0.050 (2)	0.066 (3)	0.062 (3)	−0.003 (2)	−0.005 (2)	−0.002 (2)
C13	0.059 (3)	0.060 (3)	0.052 (3)	−0.004 (2)	0.005 (2)	−0.001 (2)
C14	0.048 (2)	0.051 (2)	0.054 (3)	−0.005 (2)	0.006 (2)	−0.005 (2)

O1—C8	1.378 (4)	C3—H3	0.9300
O1—C14	1.379 (4)	C4—C5	1.380 (5)
O2—N2	1.212 (4)	C4—H4	0.9300
O3—N2	1.218 (5)	C5—C6	1.376 (5)
N1—C8	1.299 (4)	C5—C8	1.452 (5)
N1—C9	1.396 (5)	C6—C7	1.381 (5)
N2—C12	1.465 (5)	C6—H6	0.9300
C1—C2	1.506 (5)	C7—H7	0.9300
C1—H1A	0.9600	C9—C14	1.387 (5)
C1—H1B	0.9600	C9—C10	1.389 (5)
C1—H1C	0.9600	C10—C11	1.383 (6)
C1—H1D	0.9600	C10—H10	0.9300
C1—H1E	0.9600	C11—C12	1.380 (5)
C1—H1F	0.9600	C11—H11	0.9300
C2—C7	1.373 (6)	C12—C13	1.380 (5)
C2—C3	1.375 (6)	C13—C14	1.366 (5)
C3—C4	1.381 (6)	C13—H13	0.9300
C8—O1—C14	104.2 (3)	C5—C4—H4	120.1
C8—N1—C9	104.6 (3)	C3—C4—H4	120.1
O2—N2—O3	122.3 (4)	C6—C5—C4	118.4 (4)
O2—N2—C12	118.5 (4)	C6—C5—C8	121.4 (4)
O3—N2—C12	119.1 (4)	C4—C5—C8	120.2 (4)
C2—C1—H1A	109.5	C5—C6—C7	121.0 (4)
C2—C1—H1B	109.5	C5—C6—H6	119.5
H1A—C1—H1B	109.5	C7—C6—H6	119.5
C2—C1—H1C	109.5	C2—C7—C6	121.0 (4)
H1A—C1—H1C	109.5	C2—C7—H7	119.5
H1B—C1—H1C	109.5	C6—C7—H7	119.5
C2—C1—H1D	109.5	N1—C8—O1	114.8 (3)
H1A—C1—H1D	141.1	N1—C8—C5	128.7 (4)
H1B—C1—H1D	56.3	O1—C8—C5	116.6 (3)
H1C—C1—H1D	56.3	C14—C9—C10	119.5 (4)
C2—C1—H1E	109.5	C14—C9—N1	109.0 (3)
H1A—C1—H1E	56.3	C10—C9—N1	131.4 (4)
H1B—C1—H1E	141.1	C11—C10—C9	117.4 (4)
H1C—C1—H1E	56.3	C11—C10—H10	121.3
H1D—C1—H1E	109.5	C9—C10—H10	121.3
C2—C1—H1F	109.5	C12—C11—C10	120.1 (4)
H1A—C1—H1F	56.3	C12—C11—H11	119.9
H1B—C1—H1F	56.3	C10—C11—H11	119.9
H1C—C1—H1F	141.1	C13—C12—C11	124.4 (4)
H1D—C1—H1F	109.5	C13—C12—N2	117.3 (4)
H1E—C1—H1F	109.5	C11—C12—N2	118.3 (4)
C7—C2—C3	117.7 (4)	C14—C13—C12	113.7 (4)
C7—C2—C1	121.1 (4)	C14—C13—H13	123.1
C3—C2—C1	121.2 (4)	C12—C13—H13	123.1
C2—C3—C4	122.0 (4)	C13—C14—O1	127.8 (4)
C2—C3—H3	119.0	C13—C14—C9	124.8 (4)
C4—C3—H3	119.0	O1—C14—C9	107.4 (4)
C5—C4—C3	119.9 (4)
C7—C2—C3—C4	2.4 (7)	N1—C9—C10—C11	−179.9 (4)
C1—C2—C3—C4	−177.7 (4)	C9—C10—C11—C12	−1.1 (7)
C2—C3—C4—C5	−2.1 (7)	C10—C11—C12—C13	0.8 (7)
C3—C4—C5—C6	0.5 (7)	C10—C11—C12—N2	179.8 (4)
C3—C4—C5—C8	−178.9 (4)	O2—N2—C12—C13	172.0 (4)
C4—C5—C6—C7	0.8 (6)	O3—N2—C12—C13	−5.9 (7)
C8—C5—C6—C7	−179.8 (4)	O2—N2—C12—C11	−7.0 (7)
C3—C2—C7—C6	−1.0 (6)	O3—N2—C12—C11	175.1 (5)
C1—C2—C7—C6	179.0 (4)	C11—C12—C13—C14	0.0 (6)
C5—C6—C7—C2	−0.6 (7)	N2—C12—C13—C14	−179.0 (4)
C9—N1—C8—O1	−0.3 (4)	C12—C13—C14—O1	179.4 (4)
C9—N1—C8—C5	179.6 (4)	C12—C13—C14—C9	−0.6 (6)
C14—O1—C8—N1	0.7 (4)	C8—O1—C14—C13	179.2 (4)
C14—O1—C8—C5	−179.2 (3)	C8—O1—C14—C9	−0.8 (4)
C6—C5—C8—N1	174.5 (4)	C10—C9—C14—C13	0.3 (6)
C4—C5—C8—N1	−6.1 (7)	N1—C9—C14—C13	−179.3 (3)
C6—C5—C8—O1	−5.6 (6)	C10—C9—C14—O1	−179.7 (3)
C4—C5—C8—O1	173.8 (4)	N1—C9—C14—O1	0.7 (4)
C8—N1—C9—C14	−0.2 (4)	C4—C5—C8—N1	−6.1 (7)
C8—N1—C9—C10	−179.8 (4)	C4—C5—C8—O1	173.8 (4)
C14—C9—C10—C11	0.5 (6)	C11—C12—N2—O3	175.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.61	3.502 (6)	160
C1—H1B···O2ii	0.96	2.80	3.143 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.61	3.502 (6)	160
C1—H1B⋯O2ii	0.96	2.80	3.143 (5)	102

Symmetry codes: (i) ; (ii) .