2-(4-Amino-phen-yl)-1,3-benzoxazole.

In the title mol-ecule, C(13)H(10)N(2)O, the dihedral angle between the benzoxazole ring system and the benzene ring is 11.8 (1)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds and π⋯π inter-actions [centroid-centroid distance = 3.6560 (15) Å] to form a two-dimensional network.

Related literature

For related literature, see: Prudhomme et al. (1986 ▶); Vinsova et al. (2005 ▶).

Experimental

Crystal data

C13H10N2O

M = 210.23

Monoclinic,

a = 4.1461 (3) Å

b = 19.5420 (12) Å

c = 12.7705 (8) Å

β = 95.243 (1)°

V = 1030.38 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.974, T max = 0.987

4628 measured reflections

1902 independent reflections

1315 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.151

S = 1.08

1902 reflections

151 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801653X/lh2630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801653X/lh2630Isup2.hkl

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

C13H10N2O	F000 = 440
Mr = 210.23	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1089 reflections
a = 4.1461 (3) Å	θ = 2.6–22.6º
b = 19.5420 (12) Å	µ = 0.09 mm−1
c = 12.7705 (8) Å	T = 298 (2) K
β = 95.243 (1)º	Block, brown
V = 1030.38 (12) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	1902 independent reflections
Radiation source: fine-focus sealed tube	1315 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.086
T = 298(2) K	θmax = 25.5º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −4→5
Tmin = 0.974, Tmax = 0.987	k = −23→17
4628 measured reflections	l = −14→15

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.0374P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1902 reflections	Δρmax = 0.17 e Å−3
151 parameters	Δρmin = −0.22 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	1.1291 (4)	0.93054 (9)	0.09030 (12)	0.0548 (5)
N1	1.0571 (5)	0.89549 (10)	0.25399 (15)	0.0508 (6)
C8	0.8394 (6)	0.82440 (13)	0.10509 (18)	0.0471 (6)
C7	1.0044 (6)	0.88277 (13)	0.15444 (18)	0.0472 (6)
C13	0.6743 (6)	0.77900 (13)	0.16499 (19)	0.0522 (7)
H13	0.6617	0.7882	0.2360	0.063*
C11	0.5492 (6)	0.70536 (14)	0.01598 (19)	0.0511 (7)
C1	1.2748 (6)	0.97814 (13)	0.15893 (18)	0.0488 (7)
N2	0.4179 (7)	0.64627 (14)	−0.02632 (19)	0.0746 (8)
H2B	0.430 (7)	0.6376 (13)	−0.0924 (9)	0.090 (1)*
H2A	0.300 (6)	0.6220 (12)	0.0115 (19)	0.090 (1)*
C6	1.2309 (6)	0.95673 (13)	0.25916 (18)	0.0487 (7)
C12	0.5301 (6)	0.72124 (13)	0.1221 (2)	0.0561 (7)
H12	0.4183	0.6923	0.1638	0.067*
C9	0.8540 (6)	0.80871 (14)	−0.00072 (18)	0.0529 (7)
H9	0.9622	0.8382	−0.0428	0.064*
C2	1.4362 (7)	1.03717 (14)	0.1363 (2)	0.0630 (8)
H2	1.4620	1.0504	0.0676	0.076*
C5	1.3567 (7)	0.99539 (15)	0.3444 (2)	0.0615 (8)
H5	1.3315	0.9819	0.4130	0.074*
C10	0.7122 (6)	0.75067 (14)	−0.04423 (19)	0.0556 (7)
H10	0.7254	0.7415	−0.1152	0.067*
C3	1.5567 (7)	1.07529 (15)	0.2214 (2)	0.0664 (8)
H3	1.6650	1.1159	0.2103	0.080*
C4	1.5205 (7)	1.05458 (16)	0.3237 (2)	0.0640 (8)
H4	1.6088	1.0812	0.3795	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0637 (12)	0.0592 (12)	0.0423 (10)	0.0044 (9)	0.0097 (8)	0.0024 (9)
N1	0.0542 (13)	0.0567 (15)	0.0422 (12)	0.0052 (11)	0.0075 (9)	0.0029 (10)
C8	0.0499 (15)	0.0475 (16)	0.0443 (14)	0.0116 (12)	0.0062 (11)	0.0034 (12)
C7	0.0491 (15)	0.0520 (17)	0.0419 (14)	0.0135 (13)	0.0115 (11)	0.0073 (12)
C13	0.0545 (16)	0.0579 (19)	0.0453 (15)	0.0110 (14)	0.0119 (12)	−0.0013 (13)
C11	0.0529 (16)	0.0502 (17)	0.0502 (15)	0.0121 (13)	0.0053 (12)	−0.0028 (13)
C1	0.0528 (16)	0.0470 (16)	0.0469 (15)	0.0099 (13)	0.0059 (11)	−0.0013 (12)
N2	0.097 (2)	0.0717 (19)	0.0584 (15)	−0.0086 (15)	0.0221 (14)	−0.0112 (14)
C6	0.0493 (15)	0.0537 (17)	0.0439 (14)	0.0127 (13)	0.0082 (11)	0.0023 (12)
C12	0.0601 (17)	0.0587 (19)	0.0518 (16)	0.0057 (14)	0.0173 (13)	0.0044 (13)
C9	0.0594 (17)	0.0594 (18)	0.0410 (14)	0.0089 (14)	0.0103 (11)	0.0072 (12)
C2	0.071 (2)	0.063 (2)	0.0568 (17)	0.0044 (16)	0.0167 (14)	0.0039 (15)
C5	0.0651 (18)	0.072 (2)	0.0468 (16)	0.0091 (16)	0.0051 (13)	−0.0044 (14)
C10	0.0680 (18)	0.0591 (19)	0.0408 (14)	0.0067 (15)	0.0111 (13)	−0.0006 (13)
C3	0.067 (2)	0.063 (2)	0.070 (2)	−0.0023 (15)	0.0143 (15)	−0.0052 (16)
C4	0.0577 (18)	0.069 (2)	0.0643 (19)	0.0032 (16)	0.0024 (14)	−0.0143 (15)

O1—C7	1.374 (3)	N2—H2B	0.868 (10)
O1—C1	1.379 (3)	N2—H2A	0.859 (10)
N1—C7	1.294 (3)	C6—C5	1.387 (3)
N1—C6	1.395 (3)	C12—H12	0.9300
C8—C13	1.392 (3)	C9—C10	1.372 (3)
C8—C9	1.392 (3)	C9—H9	0.9300
C8—C7	1.445 (4)	C2—C3	1.373 (4)
C13—C12	1.368 (3)	C2—H2	0.9300
C13—H13	0.9300	C5—C4	1.379 (4)
C11—N2	1.367 (4)	C5—H5	0.9300
C11—C10	1.388 (3)	C10—H10	0.9300
C11—C12	1.399 (3)	C3—C4	1.389 (4)
C1—C6	1.374 (3)	C3—H3	0.9300
C1—C2	1.378 (4)	C4—H4	0.9300
C7—O1—C1	104.26 (18)	C5—C6—N1	131.3 (2)
C7—N1—C6	104.6 (2)	C13—C12—C11	120.6 (2)
C13—C8—C9	117.4 (2)	C13—C12—H12	119.7
C13—C8—C7	120.0 (2)	C11—C12—H12	119.7
C9—C8—C7	122.4 (2)	C10—C9—C8	121.4 (2)
N1—C7—O1	114.6 (2)	C10—C9—H9	119.3
N1—C7—C8	127.7 (2)	C8—C9—H9	119.3
O1—C7—C8	117.7 (2)	C3—C2—C1	115.9 (3)
C12—C13—C8	121.7 (2)	C3—C2—H2	122.0
C12—C13—H13	119.2	C1—C2—H2	122.0
C8—C13—H13	119.2	C4—C5—C6	117.5 (2)
N2—C11—C10	121.1 (2)	C4—C5—H5	121.2
N2—C11—C12	121.0 (2)	C6—C5—H5	121.2
C10—C11—C12	117.9 (2)	C9—C10—C11	121.0 (2)
C6—C1—C2	123.9 (2)	C9—C10—H10	119.5
C6—C1—O1	107.4 (2)	C11—C10—H10	119.5
C2—C1—O1	128.7 (2)	C2—C3—C4	121.6 (3)
C11—N2—H2B	119.6 (19)	C2—C3—H3	119.2
C11—N2—H2A	118 (2)	C4—C3—H3	119.2
H2B—N2—H2A	122 (3)	C5—C4—C3	121.5 (3)
C1—C6—C5	119.5 (3)	C5—C4—H4	119.3
C1—C6—N1	109.2 (2)	C3—C4—H4	119.3
C6—N1—C7—O1	0.1 (3)	C7—N1—C6—C5	−179.6 (3)
C6—N1—C7—C8	178.5 (2)	C8—C13—C12—C11	1.1 (4)
C1—O1—C7—N1	−0.1 (3)	N2—C11—C12—C13	177.1 (3)
C1—O1—C7—C8	−178.7 (2)	C10—C11—C12—C13	−1.4 (4)
C13—C8—C7—N1	9.5 (4)	C13—C8—C9—C10	−0.2 (4)
C9—C8—C7—N1	−166.4 (2)	C7—C8—C9—C10	175.9 (2)
C13—C8—C7—O1	−172.1 (2)	C6—C1—C2—C3	0.1 (4)
C9—C8—C7—O1	12.0 (3)	O1—C1—C2—C3	179.7 (2)
C9—C8—C13—C12	−0.3 (4)	C1—C6—C5—C4	0.4 (4)
C7—C8—C13—C12	−176.4 (2)	N1—C6—C5—C4	179.9 (2)
C7—O1—C1—C6	0.1 (2)	C8—C9—C10—C11	−0.1 (4)
C7—O1—C1—C2	−179.6 (2)	N2—C11—C10—C9	−177.6 (3)
C2—C1—C6—C5	−0.7 (4)	C12—C11—C10—C9	0.9 (4)
O1—C1—C6—C5	179.6 (2)	C1—C2—C3—C4	0.9 (4)
C2—C1—C6—N1	179.7 (2)	C6—C5—C4—C3	0.5 (4)
O1—C1—C6—N1	0.0 (3)	C2—C3—C4—C5	−1.2 (4)
C7—N1—C6—C1	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1i	0.868 (10)	2.174 (12)	3.028 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1i	0.868 (10)	2.174 (12)	3.028 (3)	168 (3)

Symmetry code: (i) .