2-(4-Amino­phen­yl)-1,3-benzoxazole

Qu, Y.; Zhang, S.; Teng, L.; Xia, X.; Zhang, Y.

doi:10.1107/S160053680801653X

organic compounds

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Volume 64| Part 7| July 2008| Page o1210

doi:10.1107/S160053680801653X

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2-(4-Aminophenyl)-1,3-benzoxazole

Yuan Qu,^a Shi-lei Zhang,^a Lei Teng,^a Xian-you Xia ^a and Yong Zhang ^a ^*

^aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: zy0340907@yahoo.com.cn

(Received 19 May 2008; accepted 30 May 2008; online 7 June 2008)

In the title molecule, C₁₃H₁₀N₂O, the dihedral angle between the benzoxazole ring system and the benzene ring is 11.8 (1)°. In the crystal structure, molecules are linked by intermolecular N—H⋯N hydrogen bonds and π⋯π interactions [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_r = 210.23
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.151
S = 1.08
1902 reflections
151 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The benzoxazole rings sytem is one of the most common heterocycles in medicinal chemistry. Previous reports revealed that substituted benzoxazoles possess diverse chemotherapeutic activities including antibiotic, antimicrobial, antiviral and antitumor activities (Prudhomme et al., 1986; Vinsova et al., 2005). With this mind, the title compound, (I), was prepared in a series of syntheses to produce new benzoxazole derivatives, and we report the crystal stucture herein.

The molecular structure of (I) is illustrated in Fig. 1. In (I), the benzixazole rings system is not co-planar with the benzene ring, the dihedral angle being 11.8 (1)°. In the crystal structure, molecules are linked by N2—H2B···N1ⁱ hydrogen bonds (symmetry code: (i) x -1/2, 3/2 - y, z - 1/2) into a one-dimensional chains along [101] (Fig. 2). Neighbouring chains are further linked into a two-dimensional network by π..π interactions with Cg1···Cg2(-1+x, y, z) = 3.6560 (15) Å where Cg1 and Cg2 are the centroids defined by the ring atoms O1/C1/C6/N1/C7 and C1-C6 respectivley. There are no significant interactions between the adjacent layers.

Related literature top

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

Experimental top

All reagents and solvents were used as obtained without further purification. 4-aminobenzoic acid (13.7 g, 0.1 mol) and 2-aminophenol (10.9 g, 0.1 mmol) were mixed together with polyphosphoric acid (50 g) and heated to 493 K under N₂ atmosphere for 4 h. The reaction mixture was cooled to room temperature and poured into 10% K₂CO₃ solution. The precipitate was filtered under reduced pressure. Brown crystals were obtained by recrystallization from acetone-water.Yield: 88%; Analysis calculated for C₁₃H₁₀N₂O: C 74.29, H 4.76, N 13.33%; found: C 74.26, H 4.78, N 13.35%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. Part of the crystal packing showing the formation of the [101] chains linked by by N—H···N hydrogen bonds shown as dashed lines.
	Fig. 3. Part of the crystal packing showing the formation of the two-dimensional layers formed by by N—H···N hydrogen bonds shown as dashed lines and π···π interactions. For clarity, H atoms not involved in the motif have been omitted.

2-(4-Aminophenyl)-1,3-benzoxazole top

Crystal data top

C₁₃H₁₀N₂O	F(000) = 440
M_r = 210.23	D_x = 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 = 2.6–22.6°
b = 19.5420 (12) Å	µ = 0.09 mm⁻¹
c = 12.7705 (8) Å	T = 298 K
β = 95.243 (1)°	Block, brown
V = 1030.38 (12) Å³	0.30 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1902 independent reflections
Radiation source: fine-focus sealed tube	1315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −4→5
T_min = 0.974, T_max = 0.987	k = −23→17
4628 measured reflections	l = −14→15

Refinement top

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0636P)² + 0.0374P] where P = (F_o² + 2F_c²)/3
1902 reflections	(Δ/σ)_max < 0.001
151 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₃H₁₀N₂O	V = 1030.38 (12) Å³
M_r = 210.23	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.1461 (3) Å	µ = 0.09 mm⁻¹
b = 19.5420 (12) Å	T = 298 K
c = 12.7705 (8) Å	0.30 × 0.20 × 0.15 mm
β = 95.243 (1)°

Data collection top

Bruker SMART CCD diffractometer	1902 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1315 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.987	R_int = 0.086
4628 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	2 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.17 e Å⁻³
1902 reflections	Δρ_min = −0.22 e Å⁻³
151 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1ⁱ	0.87 (1)	2.17 (1)	3.028 (3)	168 (3)

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O
M_r	210.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	4.1461 (3), 19.5420 (12), 12.7705 (8)
β (°)	95.243 (1)
V (Å³)	1030.38 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.974, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	4628, 1902, 1315
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.151, 1.09
No. of reflections	1902
No. of parameters	151
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z−1/2.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Prudhomme, M., Guyot, J. & Jeminet, G. (1986). J. Antibiot. 39, 934–937. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vinsova, J., Horak, V., Buchta, V. & Kaustova, J. (2005). Molecules, 10, 783–793. Web of Science CrossRef PubMed CAS Google Scholar

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doi:10.1107/S160053680801653X

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