organic compounds
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
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); Lv et al. (2010); Tang et al. (2007).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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.
Supporting information
https://doi.org/10.1107/S1600536812040640/im2386sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040640/im2386Isup2.hkl
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%.
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).
Oxadiazole is the parent compound for a vast class of
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 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 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).
Data collection: CrysAlis PRO (Agilent, 2011); cell
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).C8H7N3O | F(000) = 336 |
Mr = 161.17 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
a = 11.194 (3) Å | Cell parameters from 656 reflections |
b = 5.8990 (5) Å | θ = 3.5–26.3° |
c = 15.034 (5) Å | µ = 0.10 mm−1 |
β = 130.193 (18)° | T = 291 K |
V = 758.3 (3) Å3 | Prism, colourless |
Z = 4 | 0.26 × 0.24 × 0.22 mm |
Agilent Xcalibur Eos Gemini diffractometer | 1551 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 877 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 16.2312 pixels mm-1 | θmax = 26.4°, θmin = 3.6° |
ω scans | h = −13→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −4→7 |
Tmin = 0.851, Tmax = 1.000 | l = −18→17 |
2912 measured reflections |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C8H7N3O | V = 758.3 (3) Å3 |
Mr = 161.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.194 (3) Å | µ = 0.10 mm−1 |
b = 5.8990 (5) Å | T = 291 K |
c = 15.034 (5) Å | 0.26 × 0.24 × 0.22 mm |
β = 130.193 (18)° |
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 = 1.000 | Rint = 0.040 |
2912 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
1551 reflections | Δρmin = −0.15 e Å−3 |
109 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.15541 (17) | 0.6145 (2) | 0.02276 (13) | 0.0495 (5) | |
N1 | −0.2177 (2) | 0.2637 (3) | −0.04164 (18) | 0.0617 (7) | |
N2 | −0.3435 (2) | 0.4062 (3) | −0.12624 (17) | 0.0594 (7) | |
N3 | −0.3795 (2) | 0.8025 (3) | −0.12550 (17) | 0.0622 (7) | |
H3A | −0.4628 | 0.8128 | −0.2012 | 0.075* | |
H3B | −0.3161 | 0.9341 | −0.0922 | 0.075* | |
C1 | 0.1056 (3) | 0.1191 (4) | 0.1680 (2) | 0.0624 (8) | |
H1 | 0.0506 | 0.0125 | 0.1084 | 0.075* | |
C2 | 0.2512 (3) | 0.0674 (4) | 0.2723 (3) | 0.0683 (9) | |
H2 | 0.2942 | −0.0749 | 0.2825 | 0.082* | |
C3 | 0.3329 (3) | 0.2221 (5) | 0.3606 (2) | 0.0714 (9) | |
H3 | 0.4308 | 0.1850 | 0.4303 | 0.086* | |
C4 | 0.2704 (3) | 0.4311 (5) | 0.3463 (2) | 0.0720 (9) | |
H4 | 0.3259 | 0.5365 | 0.4065 | 0.086* | |
C5 | 0.1250 (3) | 0.4866 (4) | 0.2428 (2) | 0.0578 (8) | |
H5 | 0.0828 | 0.6292 | 0.2336 | 0.069* | |
C6 | 0.0423 (3) | 0.3320 (4) | 0.1532 (2) | 0.0457 (6) | |
C7 | −0.1115 (3) | 0.3912 (4) | 0.0434 (2) | 0.0450 (6) | |
C8 | −0.3014 (3) | 0.6083 (4) | −0.0839 (2) | 0.0477 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0394 (10) | 0.0366 (9) | 0.0426 (9) | −0.0023 (7) | 0.0129 (8) | −0.0024 (7) |
N1 | 0.0457 (13) | 0.0409 (11) | 0.0551 (13) | −0.0007 (10) | 0.0129 (11) | −0.0039 (10) |
N2 | 0.0413 (12) | 0.0417 (12) | 0.0529 (13) | −0.0017 (10) | 0.0112 (11) | −0.0038 (10) |
N3 | 0.0462 (13) | 0.0409 (12) | 0.0514 (13) | 0.0025 (10) | 0.0097 (11) | 0.0036 (10) |
C1 | 0.0511 (17) | 0.0476 (15) | 0.0623 (17) | −0.0008 (13) | 0.0247 (15) | −0.0049 (13) |
C2 | 0.0508 (17) | 0.0531 (16) | 0.0730 (19) | 0.0128 (14) | 0.0273 (16) | 0.0128 (14) |
C3 | 0.0463 (16) | 0.075 (2) | 0.0537 (18) | 0.0022 (15) | 0.0143 (14) | 0.0111 (15) |
C4 | 0.0611 (19) | 0.067 (2) | 0.0468 (16) | −0.0069 (16) | 0.0164 (15) | −0.0053 (14) |
C5 | 0.0522 (17) | 0.0457 (14) | 0.0529 (16) | 0.0005 (12) | 0.0236 (15) | −0.0019 (12) |
C6 | 0.0391 (14) | 0.0415 (13) | 0.0467 (14) | 0.0012 (11) | 0.0232 (12) | 0.0037 (11) |
C7 | 0.0404 (14) | 0.0330 (12) | 0.0487 (14) | −0.0002 (11) | 0.0229 (12) | 0.0003 (11) |
C8 | 0.0365 (14) | 0.0447 (14) | 0.0422 (13) | −0.0044 (12) | 0.0164 (12) | −0.0025 (12) |
O1—C7 | 1.369 (2) | C1—C6 | 1.387 (3) |
O1—C8 | 1.364 (3) | C2—H2 | 0.9300 |
N1—N2 | 1.413 (3) | C2—C3 | 1.366 (4) |
N1—C7 | 1.285 (3) | C3—H3 | 0.9300 |
N2—C8 | 1.289 (3) | C3—C4 | 1.364 (4) |
N3—H3A | 0.8936 | C4—H4 | 0.9300 |
N3—H3B | 0.9476 | C4—C5 | 1.382 (3) |
N3—C8 | 1.328 (3) | C5—H5 | 0.9300 |
C1—H1 | 0.9300 | C5—C6 | 1.376 (3) |
C1—C2 | 1.382 (3) | C6—C7 | 1.464 (3) |
C8—O1—C7 | 102.89 (16) | C3—C4—H4 | 119.9 |
C7—N1—N2 | 106.97 (18) | C3—C4—C5 | 120.2 (2) |
C8—N2—N1 | 105.75 (18) | C5—C4—H4 | 119.9 |
H3A—N3—H3B | 115.3 | C4—C5—H5 | 119.8 |
C8—N3—H3A | 119.2 | C6—C5—C4 | 120.3 (2) |
C8—N3—H3B | 114.6 | C6—C5—H5 | 119.8 |
C2—C1—H1 | 120.4 | C1—C6—C7 | 120.3 (2) |
C2—C1—C6 | 119.2 (2) | C5—C6—C1 | 119.5 (2) |
C6—C1—H1 | 120.4 | C5—C6—C7 | 120.3 (2) |
C1—C2—H2 | 119.5 | O1—C7—C6 | 118.30 (19) |
C3—C2—C1 | 121.0 (2) | N1—C7—O1 | 111.77 (19) |
C3—C2—H2 | 119.5 | N1—C7—C6 | 129.9 (2) |
C2—C3—H3 | 120.1 | N2—C8—O1 | 112.6 (2) |
C4—C3—C2 | 119.8 (3) | N2—C8—N3 | 130.2 (2) |
C4—C3—H3 | 120.1 | N3—C8—O1 | 117.12 (19) |
N1—N2—C8—O1 | 0.7 (3) | C4—C5—C6—C1 | 0.5 (4) |
N1—N2—C8—N3 | −176.1 (3) | C4—C5—C6—C7 | −179.8 (2) |
N2—N1—C7—O1 | −0.4 (3) | C5—C6—C7—O1 | 13.9 (3) |
N2—N1—C7—C6 | −180.0 (2) | C5—C6—C7—N1 | −166.5 (3) |
C1—C2—C3—C4 | 0.1 (5) | C6—C1—C2—C3 | 0.3 (4) |
C1—C6—C7—O1 | −166.5 (2) | C7—O1—C8—N2 | −0.9 (3) |
C1—C6—C7—N1 | 13.1 (4) | C7—O1—C8—N3 | 176.4 (2) |
C2—C1—C6—C5 | −0.5 (4) | C7—N1—N2—C8 | −0.2 (3) |
C2—C1—C6—C7 | 179.8 (3) | C8—O1—C7—N1 | 0.8 (3) |
C2—C3—C4—C5 | −0.1 (5) | C8—O1—C7—C6 | −179.6 (2) |
C3—C4—C5—C6 | −0.2 (4) |
D—H···A | D—H | H···A | D···A | 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+1/2, −z−1/2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C8H7N3O |
Mr | 161.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 11.194 (3), 5.8990 (5), 15.034 (5) |
β (°) | 130.193 (18) |
V (Å3) | 758.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Agilent Xcalibur Eos Gemini |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.851, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2912, 1551, 877 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.137, 1.02 |
No. of reflections | 1551 |
No. of parameters | 109 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N2i | 0.89 | 2.12 | 2.997 (3) | 168.7 |
N3—H3B···N1ii | 0.95 | 2.12 | 3.054 (3) | 168.4 |
Symmetry codes: (i) −x−1, y+1/2, −z−1/2; (ii) x, y+1, z. |
Acknowledgements
We gratefully acknowledge financial support by the National Natural Science Foundation of China (No. 21171149).
References
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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.