organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Phenyl-1,3,4-oxa­diazol-2-amine

aDepartment of Chemistry, Zhengzhou University, Zhengzhou, 450052, People's Republic of China
*Correspondence e-mail: xuyan@zzu.edu.cn

(Received 5 June 2012; accepted 26 September 2012; online 29 September 2012)

In the title complex, C8H7N3O, the C—O [1.369 (2) and 1.364 (3) Å] and C=N [1.285 (3) and 1.289 (3) Å] bond lengths in the oxadiazole ring are each almost identical within systematic errors, although different substituents are attached to the ring. The phenyl ring is inclined to the planar oxadiazole ring [r.m.s. deviation 0.002 Å] by 13.42 (18)°. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming double-stranded chains propagating along [010].

Related literature

For background to 5-phenyl-1,3,4-oxadiazol-2-amines and the synthesis of the title compound, see: Bachwani et al. (2011[Bachwani, M., Sharma, V. & Kumar, R. (2011). Intl. Res. J. Pharm. 5, 84-89.]); Lv et al. (2010[Lv, H.-S., Zhao, B.-X., Li, J.-K., Xia, Y., Lian, S., Liu, W.-Y. & Gong, Z.-L. (2010). Dyes Pigments, 86, 25-31.]); Tang et al. (2007[Tang, X.-L., Dou, W., Chen, S.-W., Dang, F.-F. & Liu, W.-S. (2007). Spectrochim. Acta A, 68, 349-353.]).

[Scheme 1]

Experimental

Crystal data
  • C8H7N3O

  • Mr = 161.17

  • Monoclinic, P 21 /c

  • a = 11.194 (3) Å

  • b = 5.8990 (5) Å

  • c = 15.034 (5) Å

  • β = 130.193 (18)°

  • V = 758.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 291 K

  • 0.26 × 0.24 × 0.22 mm

Data collection
  • Agilent Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.851, Tmax = 1.000

  • 2912 measured reflections

  • 1551 independent reflections

  • 877 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.137

  • S = 1.02

  • 1551 reflections

  • 109 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯N2i 0.89 2.12 2.997 (3) 169
N3—H3B⋯N1ii 0.95 2.12 3.054 (3) 168
Symmetry codes: (i) [-x-1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

Oxadiazole is the parent compound for a vast class of heterocyclic compounds. Oxadiazole derivatives have attracted considerable attention (Bachwani et al., 2011). Although 1,3,4-oxadiazole exhibit various N and O atoms that should allow to form single crystals due to their ability to act as hydrogen bond acceptor sites, there have been limited studies concerning their crystal properties. To further explore their crystal properties, in this communication, we report the crystal structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. As shown in figure 1, the bond length between the O1 with C7 is nearly to the bond length between the O1 with C8, they are 1.369 (2) Å and 1.364 (3) Å. Similarly, the distance of the bond between the C7 and N1 is 1.285 (3) Å and the distance of the bond between the C8 and N2 is 1.289 (3) Å. The bond length between N1 with N2 is 1.413 (3) Å and the bond length between N3 with C8 is 1.328 (3) Å. In the crystal structure, the C7—N1—N2 and C8—N2—N1 angles are 106.97 (18) ° and 105.75 (19) °. The torsion angle between C(7)—N(1)—N(2)—C(8) is 0.2 (3) ° demonstrating the planarity of the heterocyclic moiety. Classical intermolecular N(1)—H···N(3) (3.054 Å) and N(2)—H···N(3) (2.997 Å) hydrogen bonds link the adjacent molecules into a two-dimensional structure.

Related literature top

For background to 5-phenyl-1,3,4-oxadiazol-2-amines and the synthesis of the title compound, see: Bachwani et al. (2011); Lv et al. (2010); Tang et al. (2007).

Experimental top

Benzaldehyde (0.01 mol) and ethanol (20 ml) were added to semicarbazide hydrochloride (0.011 mol) and the reaction mixture was refluxed for 2 h. Afterwards the obtained semicarbazone (0.01 mol) was dissolved in acetic acid together with bromine (0.65 ml) and the solution was stirred for 30 minutes. The resulting precipitate (0.02 mmol) was dissolved in a ethanol (3 ml) water (3 ml) mixture. The resulting solution was allowed to stand at room temperature for about two weeks days. Colourless crystals were obtained in a yield of 43%.

Refinement top

All H atoms are positioned geometrically with C—H = 0.93 Å and N—H = 0.95 Å and refined as riding atoms with Uiso(H) = 1.2Ueq(C,N).

Structure description top

Oxadiazole is the parent compound for a vast class of heterocyclic compounds. Oxadiazole derivatives have attracted considerable attention (Bachwani et al., 2011). Although 1,3,4-oxadiazole exhibit various N and O atoms that should allow to form single crystals due to their ability to act as hydrogen bond acceptor sites, there have been limited studies concerning their crystal properties. To further explore their crystal properties, in this communication, we report the crystal structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. As shown in figure 1, the bond length between the O1 with C7 is nearly to the bond length between the O1 with C8, they are 1.369 (2) Å and 1.364 (3) Å. Similarly, the distance of the bond between the C7 and N1 is 1.285 (3) Å and the distance of the bond between the C8 and N2 is 1.289 (3) Å. The bond length between N1 with N2 is 1.413 (3) Å and the bond length between N3 with C8 is 1.328 (3) Å. In the crystal structure, the C7—N1—N2 and C8—N2—N1 angles are 106.97 (18) ° and 105.75 (19) °. The torsion angle between C(7)—N(1)—N(2)—C(8) is 0.2 (3) ° demonstrating the planarity of the heterocyclic moiety. Classical intermolecular N(1)—H···N(3) (3.054 Å) and N(2)—H···N(3) (2.997 Å) hydrogen bonds link the adjacent molecules into a two-dimensional structure.

For background to 5-phenyl-1,3,4-oxadiazol-2-amines and the synthesis of the title compound, see: Bachwani et al. (2011); Lv et al. (2010); Tang et al. (2007).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound showing thermal ellipsoids at the 30% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. View of the title complex, showing the hydrogen bonding in the crystal structure.
5-Phenyl-1,3,4-oxadiazol-2-amine top
Crystal data top
C8H7N3OF(000) = 336
Mr = 161.17Dx = 1.412 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 11.194 (3) ÅCell parameters from 656 reflections
b = 5.8990 (5) Åθ = 3.5–26.3°
c = 15.034 (5) ŵ = 0.10 mm1
β = 130.193 (18)°T = 291 K
V = 758.3 (3) Å3Prism, colourless
Z = 40.26 × 0.24 × 0.22 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
1551 independent reflections
Radiation source: Enhance (Mo) X-ray Source877 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 16.2312 pixels mm-1θmax = 26.4°, θmin = 3.6°
ω scansh = 1312
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
k = 47
Tmin = 0.851, Tmax = 1.000l = 1817
2912 measured reflections
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.054P)2]
where P = (Fo2 + 2Fc2)/3
1551 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C8H7N3OV = 758.3 (3) Å3
Mr = 161.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.194 (3) ŵ = 0.10 mm1
b = 5.8990 (5) ÅT = 291 K
c = 15.034 (5) Å0.26 × 0.24 × 0.22 mm
β = 130.193 (18)°
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
1551 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)
877 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 1.000Rint = 0.040
2912 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.02Δρmax = 0.17 e Å3
1551 reflectionsΔρmin = 0.15 e Å3
109 parameters
Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
O10.15541 (17)0.6145 (2)0.02276 (13)0.0495 (5)
N10.2177 (2)0.2637 (3)0.04164 (18)0.0617 (7)
N20.3435 (2)0.4062 (3)0.12624 (17)0.0594 (7)
N30.3795 (2)0.8025 (3)0.12550 (17)0.0622 (7)
H3A0.46280.81280.20120.075*
H3B0.31610.93410.09220.075*
C10.1056 (3)0.1191 (4)0.1680 (2)0.0624 (8)
H10.05060.01250.10840.075*
C20.2512 (3)0.0674 (4)0.2723 (3)0.0683 (9)
H20.29420.07490.28250.082*
C30.3329 (3)0.2221 (5)0.3606 (2)0.0714 (9)
H30.43080.18500.43030.086*
C40.2704 (3)0.4311 (5)0.3463 (2)0.0720 (9)
H40.32590.53650.40650.086*
C50.1250 (3)0.4866 (4)0.2428 (2)0.0578 (8)
H50.08280.62920.23360.069*
C60.0423 (3)0.3320 (4)0.1532 (2)0.0457 (6)
C70.1115 (3)0.3912 (4)0.0434 (2)0.0450 (6)
C80.3014 (3)0.6083 (4)0.0839 (2)0.0477 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0394 (10)0.0366 (9)0.0426 (9)0.0023 (7)0.0129 (8)0.0024 (7)
N10.0457 (13)0.0409 (11)0.0551 (13)0.0007 (10)0.0129 (11)0.0039 (10)
N20.0413 (12)0.0417 (12)0.0529 (13)0.0017 (10)0.0112 (11)0.0038 (10)
N30.0462 (13)0.0409 (12)0.0514 (13)0.0025 (10)0.0097 (11)0.0036 (10)
C10.0511 (17)0.0476 (15)0.0623 (17)0.0008 (13)0.0247 (15)0.0049 (13)
C20.0508 (17)0.0531 (16)0.0730 (19)0.0128 (14)0.0273 (16)0.0128 (14)
C30.0463 (16)0.075 (2)0.0537 (18)0.0022 (15)0.0143 (14)0.0111 (15)
C40.0611 (19)0.067 (2)0.0468 (16)0.0069 (16)0.0164 (15)0.0053 (14)
C50.0522 (17)0.0457 (14)0.0529 (16)0.0005 (12)0.0236 (15)0.0019 (12)
C60.0391 (14)0.0415 (13)0.0467 (14)0.0012 (11)0.0232 (12)0.0037 (11)
C70.0404 (14)0.0330 (12)0.0487 (14)0.0002 (11)0.0229 (12)0.0003 (11)
C80.0365 (14)0.0447 (14)0.0422 (13)0.0044 (12)0.0164 (12)0.0025 (12)
Geometric parameters (Å, º) top
O1—C71.369 (2)C1—C61.387 (3)
O1—C81.364 (3)C2—H20.9300
N1—N21.413 (3)C2—C31.366 (4)
N1—C71.285 (3)C3—H30.9300
N2—C81.289 (3)C3—C41.364 (4)
N3—H3A0.8936C4—H40.9300
N3—H3B0.9476C4—C51.382 (3)
N3—C81.328 (3)C5—H50.9300
C1—H10.9300C5—C61.376 (3)
C1—C21.382 (3)C6—C71.464 (3)
C8—O1—C7102.89 (16)C3—C4—H4119.9
C7—N1—N2106.97 (18)C3—C4—C5120.2 (2)
C8—N2—N1105.75 (18)C5—C4—H4119.9
H3A—N3—H3B115.3C4—C5—H5119.8
C8—N3—H3A119.2C6—C5—C4120.3 (2)
C8—N3—H3B114.6C6—C5—H5119.8
C2—C1—H1120.4C1—C6—C7120.3 (2)
C2—C1—C6119.2 (2)C5—C6—C1119.5 (2)
C6—C1—H1120.4C5—C6—C7120.3 (2)
C1—C2—H2119.5O1—C7—C6118.30 (19)
C3—C2—C1121.0 (2)N1—C7—O1111.77 (19)
C3—C2—H2119.5N1—C7—C6129.9 (2)
C2—C3—H3120.1N2—C8—O1112.6 (2)
C4—C3—C2119.8 (3)N2—C8—N3130.2 (2)
C4—C3—H3120.1N3—C8—O1117.12 (19)
N1—N2—C8—O10.7 (3)C4—C5—C6—C10.5 (4)
N1—N2—C8—N3176.1 (3)C4—C5—C6—C7179.8 (2)
N2—N1—C7—O10.4 (3)C5—C6—C7—O113.9 (3)
N2—N1—C7—C6180.0 (2)C5—C6—C7—N1166.5 (3)
C1—C2—C3—C40.1 (5)C6—C1—C2—C30.3 (4)
C1—C6—C7—O1166.5 (2)C7—O1—C8—N20.9 (3)
C1—C6—C7—N113.1 (4)C7—O1—C8—N3176.4 (2)
C2—C1—C6—C50.5 (4)C7—N1—N2—C80.2 (3)
C2—C1—C6—C7179.8 (3)C8—O1—C7—N10.8 (3)
C2—C3—C4—C50.1 (5)C8—O1—C7—C6179.6 (2)
C3—C4—C5—C60.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N2i0.892.122.997 (3)169
N3—H3B···N1ii0.952.123.054 (3)168
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC8H7N3O
Mr161.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)11.194 (3), 5.8990 (5), 15.034 (5)
β (°) 130.193 (18)
V3)758.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.26 × 0.24 × 0.22
Data collection
DiffractometerAgilent Xcalibur Eos Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.851, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2912, 1551, 877
Rint0.040
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.137, 1.02
No. of reflections1551
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.15

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N2i0.892.122.997 (3)168.7
N3—H3B···N1ii0.952.123.054 (3)168.4
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x, y+1, z.
 

Acknowledgements

We gratefully acknowledge financial support by the National Natural Science Foundation of China (No. 21171149).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
First citationBachwani, M., Sharma, V. & Kumar, R. (2011). Intl. Res. J. Pharm. 5, 84–89.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationLv, H.-S., Zhao, B.-X., Li, J.-K., Xia, Y., Lian, S., Liu, W.-Y. & Gong, Z.-L. (2010). Dyes Pigments, 86, 25–31.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTang, X.-L., Dou, W., Chen, S.-W., Dang, F.-F. & Liu, W.-S. (2007). Spectrochim. Acta A, 68, 349–353.  CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds