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ISSN: 2056-9890

2-(4-Amino­phen­yl)-1,3-benzoxazole

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 ππ inter­actions [centroid–centroid distance = 3.6560 (15) Å] to form a two-dimensional network.

Related literature

For related literature, see: Prudhomme et al. (1986[Prudhomme, M., Guyot, J. & Jeminet, G. (1986). J. Antibiot. 39, 934-937.]); Vinsova et al. (2005[Vinsova, J., Horak, V., Buchta, V. & Kaustova, J. (2005). Molecules, 10, 783-793.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N2O

  • Mr = 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[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.987

  • 4628 measured reflections

  • 1902 independent reflections

  • 1315 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

All the aromatic H atoms were located at the geometrical positions with C—H=0.93 Å(aromatic), and the Uiso values were set 1.2 times of their carrier atoms. H2A and H2B were found in difference Fourier maps and refined with the constraint of NH=0.86 Å (amine) and Uiso(H)=1.2Ueq(N).

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
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] 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.
[Figure 3] 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
C13H10N2OF(000) = 440
Mr = 210.23Dx = 1.355 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1089 reflections
a = 4.1461 (3) Åθ = 2.6–22.6°
b = 19.5420 (12) ŵ = 0.09 mm1
c = 12.7705 (8) ÅT = 298 K
β = 95.243 (1)°Block, brown
V = 1030.38 (12) Å30.30 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1902 independent reflections
Radiation source: fine-focus sealed tube1315 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ϕ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 45
Tmin = 0.974, Tmax = 0.987k = 2317
4628 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0636P)2 + 0.0374P]
where P = (Fo2 + 2Fc2)/3
1902 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.17 e Å3
2 restraintsΔρmin = 0.22 e Å3
Crystal data top
C13H10N2OV = 1030.38 (12) Å3
Mr = 210.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.1461 (3) ŵ = 0.09 mm1
b = 19.5420 (12) ÅT = 298 K
c = 12.7705 (8) Å0.30 × 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)
Tmin = 0.974, Tmax = 0.987Rint = 0.086
4628 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0652 restraints
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.17 e Å3
1902 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
O11.1291 (4)0.93054 (9)0.09030 (12)0.0548 (5)
N11.0571 (5)0.89549 (10)0.25399 (15)0.0508 (6)
C80.8394 (6)0.82440 (13)0.10509 (18)0.0471 (6)
C71.0044 (6)0.88277 (13)0.15444 (18)0.0472 (6)
C130.6743 (6)0.77900 (13)0.16499 (19)0.0522 (7)
H130.66170.78820.23600.063*
C110.5492 (6)0.70536 (14)0.01598 (19)0.0511 (7)
C11.2748 (6)0.97814 (13)0.15893 (18)0.0488 (7)
N20.4179 (7)0.64627 (14)0.02632 (19)0.0746 (8)
H2B0.430 (7)0.6376 (13)0.0924 (9)0.090 (1)*
H2A0.300 (6)0.6220 (12)0.0115 (19)0.090 (1)*
C61.2309 (6)0.95673 (13)0.25916 (18)0.0487 (7)
C120.5301 (6)0.72124 (13)0.1221 (2)0.0561 (7)
H120.41830.69230.16380.067*
C90.8540 (6)0.80871 (14)0.00072 (18)0.0529 (7)
H90.96220.83820.04280.064*
C21.4362 (7)1.03717 (14)0.1363 (2)0.0630 (8)
H21.46201.05040.06760.076*
C51.3567 (7)0.99539 (15)0.3444 (2)0.0615 (8)
H51.33150.98190.41300.074*
C100.7122 (6)0.75067 (14)0.04423 (19)0.0556 (7)
H100.72540.74150.11520.067*
C31.5567 (7)1.07529 (15)0.2214 (2)0.0664 (8)
H31.66501.11590.21030.080*
C41.5205 (7)1.05458 (16)0.3237 (2)0.0640 (8)
H41.60881.08120.37950.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0637 (12)0.0592 (12)0.0423 (10)0.0044 (9)0.0097 (8)0.0024 (9)
N10.0542 (13)0.0567 (15)0.0422 (12)0.0052 (11)0.0075 (9)0.0029 (10)
C80.0499 (15)0.0475 (16)0.0443 (14)0.0116 (12)0.0062 (11)0.0034 (12)
C70.0491 (15)0.0520 (17)0.0419 (14)0.0135 (13)0.0115 (11)0.0073 (12)
C130.0545 (16)0.0579 (19)0.0453 (15)0.0110 (14)0.0119 (12)0.0013 (13)
C110.0529 (16)0.0502 (17)0.0502 (15)0.0121 (13)0.0053 (12)0.0028 (13)
C10.0528 (16)0.0470 (16)0.0469 (15)0.0099 (13)0.0059 (11)0.0013 (12)
N20.097 (2)0.0717 (19)0.0584 (15)0.0086 (15)0.0221 (14)0.0112 (14)
C60.0493 (15)0.0537 (17)0.0439 (14)0.0127 (13)0.0082 (11)0.0023 (12)
C120.0601 (17)0.0587 (19)0.0518 (16)0.0057 (14)0.0173 (13)0.0044 (13)
C90.0594 (17)0.0594 (18)0.0410 (14)0.0089 (14)0.0103 (11)0.0072 (12)
C20.071 (2)0.063 (2)0.0568 (17)0.0044 (16)0.0167 (14)0.0039 (15)
C50.0651 (18)0.072 (2)0.0468 (16)0.0091 (16)0.0051 (13)0.0044 (14)
C100.0680 (18)0.0591 (19)0.0408 (14)0.0067 (15)0.0111 (13)0.0006 (13)
C30.067 (2)0.063 (2)0.070 (2)0.0023 (15)0.0143 (15)0.0052 (16)
C40.0577 (18)0.069 (2)0.0643 (19)0.0032 (16)0.0024 (14)0.0143 (15)
Geometric parameters (Å, º) top
O1—C71.374 (3)N2—H2B0.868 (10)
O1—C11.379 (3)N2—H2A0.859 (10)
N1—C71.294 (3)C6—C51.387 (3)
N1—C61.395 (3)C12—H120.9300
C8—C131.392 (3)C9—C101.372 (3)
C8—C91.392 (3)C9—H90.9300
C8—C71.445 (4)C2—C31.373 (4)
C13—C121.368 (3)C2—H20.9300
C13—H130.9300C5—C41.379 (4)
C11—N21.367 (4)C5—H50.9300
C11—C101.388 (3)C10—H100.9300
C11—C121.399 (3)C3—C41.389 (4)
C1—C61.374 (3)C3—H30.9300
C1—C21.378 (4)C4—H40.9300
C7—O1—C1104.26 (18)C5—C6—N1131.3 (2)
C7—N1—C6104.6 (2)C13—C12—C11120.6 (2)
C13—C8—C9117.4 (2)C13—C12—H12119.7
C13—C8—C7120.0 (2)C11—C12—H12119.7
C9—C8—C7122.4 (2)C10—C9—C8121.4 (2)
N1—C7—O1114.6 (2)C10—C9—H9119.3
N1—C7—C8127.7 (2)C8—C9—H9119.3
O1—C7—C8117.7 (2)C3—C2—C1115.9 (3)
C12—C13—C8121.7 (2)C3—C2—H2122.0
C12—C13—H13119.2C1—C2—H2122.0
C8—C13—H13119.2C4—C5—C6117.5 (2)
N2—C11—C10121.1 (2)C4—C5—H5121.2
N2—C11—C12121.0 (2)C6—C5—H5121.2
C10—C11—C12117.9 (2)C9—C10—C11121.0 (2)
C6—C1—C2123.9 (2)C9—C10—H10119.5
C6—C1—O1107.4 (2)C11—C10—H10119.5
C2—C1—O1128.7 (2)C2—C3—C4121.6 (3)
C11—N2—H2B119.6 (19)C2—C3—H3119.2
C11—N2—H2A118 (2)C4—C3—H3119.2
H2B—N2—H2A122 (3)C5—C4—C3121.5 (3)
C1—C6—C5119.5 (3)C5—C4—H4119.3
C1—C6—N1109.2 (2)C3—C4—H4119.3
C6—N1—C7—O10.1 (3)C7—N1—C6—C5179.6 (3)
C6—N1—C7—C8178.5 (2)C8—C13—C12—C111.1 (4)
C1—O1—C7—N10.1 (3)N2—C11—C12—C13177.1 (3)
C1—O1—C7—C8178.7 (2)C10—C11—C12—C131.4 (4)
C13—C8—C7—N19.5 (4)C13—C8—C9—C100.2 (4)
C9—C8—C7—N1166.4 (2)C7—C8—C9—C10175.9 (2)
C13—C8—C7—O1172.1 (2)C6—C1—C2—C30.1 (4)
C9—C8—C7—O112.0 (3)O1—C1—C2—C3179.7 (2)
C9—C8—C13—C120.3 (4)C1—C6—C5—C40.4 (4)
C7—C8—C13—C12176.4 (2)N1—C6—C5—C4179.9 (2)
C7—O1—C1—C60.1 (2)C8—C9—C10—C110.1 (4)
C7—O1—C1—C2179.6 (2)N2—C11—C10—C9177.6 (3)
C2—C1—C6—C50.7 (4)C12—C11—C10—C90.9 (4)
O1—C1—C6—C5179.6 (2)C1—C2—C3—C40.9 (4)
C2—C1—C6—N1179.7 (2)C6—C5—C4—C30.5 (4)
O1—C1—C6—N10.0 (3)C2—C3—C4—C51.2 (4)
C7—N1—C6—C10.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···N1i0.87 (1)2.17 (1)3.028 (3)168 (3)
Symmetry code: (i) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H10N2O
Mr210.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)4.1461 (3), 19.5420 (12), 12.7705 (8)
β (°) 95.243 (1)
V3)1030.38 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.974, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
4628, 1902, 1315
Rint0.086
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.151, 1.09
No. of reflections1902
No. of parameters151
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2B···N1i0.868 (10)2.174 (12)3.028 (3)168 (3)
Symmetry code: (i) x1/2, y+3/2, z1/2.
 

References

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

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ISSN: 2056-9890
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