PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o878.
Published online 2010 March 20. doi:  10.1107/S1600536810009621
PMCID: PMC2984012

2-[4-Acetyl-5-(biphenyl-4-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]phenyl acetate

Abstract

In the title mol­ecule, C24H20N2O4, the five-membered oxadiazole ring is nearly planar (r.m.s. deviation = 0.053 Å) and the phenyl ring of the biphenyl unit attached to it forms a dihedral angle of 73.2 (1)°; the other phenyl ring is close to coplanar with the oxadiazole ring [dihedral angle = 6.2 (2)°].

Related literature

For the crystal structures of other 2,3-dihydro-1,3,4-oxa­diazo­les, see: Jin et al. (2006 [triangle]); Somogyi et al. (1992 [triangle]); Song et al. (2006 [triangle]); He & Zhu (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o878-scheme1.jpg

Experimental

Crystal data

  • C24H20N2O4
  • M r = 400.42
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o878-efi1.jpg
  • a = 8.6750 (11) Å
  • b = 12.0279 (14) Å
  • c = 19.221 (2) Å
  • V = 2005.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 16090 measured reflections
  • 2029 independent reflections
  • 1534 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.100
  • S = 1.00
  • 2029 reflections
  • 274 parameters
  • H-atom parameters constrained
  • Δρmax = 0.11 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009621/pv2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009621/pv2264Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The Schiff base reactant, N'-(4-phenylbenzylidene)-2-hydroxybenzohydrazide, features an –C(=O)–NH–N=CH linkage betwen the two aromatic systems that can be induced to form an oxadiazole. In this study, the oxadiazole is indeed formed when cyclized in acetic anhyride. The nitrogen atom in the 3-position of the ring has also been acetylated; interestingly, the hydroxy group also undergoes acetylation to yield a bis-acetylated product, the title compound. The crystal structure of the title compound is reported in this article (Fig. 1).

Experimental

The Schiff base, N'-(4-phenylbenzylidene)-2-hydroxybenzohydrazide, was synthesized by condensing 4-phenylbenzaldehyde with 2-hydrobenzhydrazide. The compound (0.5 g, 1.58 mmol) was heated in acetic anhydride (5 ml) for 2 h. The solution was cooled and then poured into crushed ice. The solid that separated solid was collected and recrystallized from methanol to give the title compound as well-formed prisms.

Refinement

The H-atoms were placed in calculated positions (C—H 0.93–98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). Due to insufficient anomalous dispersion effects, an absolute configuration could not be established. Therefore, 1495 Friedel pairs were merged.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the title compound; ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radiuii.

Crystal data

C24H20N2O4F(000) = 840
Mr = 400.42Dx = 1.326 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2292 reflections
a = 8.6750 (11) Åθ = 2.6–19.9°
b = 12.0279 (14) ŵ = 0.09 mm1
c = 19.221 (2) ÅT = 293 K
V = 2005.6 (4) Å3Prism, colorless
Z = 40.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer1534 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
graphiteθmax = 25.0°, θmin = 2.0°
ω scansh = −10→10
16090 measured reflectionsk = −14→14
2029 independent reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.100w = 1/[σ2(Fo2) + (0.0598P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2029 reflectionsΔρmax = 0.11 e Å3
274 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0082 (18)

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

xyzUiso*/Ueq
O1−0.0208 (3)1.13163 (16)0.16056 (10)0.0571 (6)
O2−0.1684 (3)1.0247 (2)0.22783 (14)0.0894 (9)
O30.3885 (2)0.96800 (17)0.22120 (10)0.0540 (5)
O40.4949 (3)1.19201 (19)0.37185 (12)0.0706 (7)
N10.2135 (3)1.09315 (19)0.25521 (13)0.0513 (6)
N20.3385 (3)1.09851 (19)0.30133 (13)0.0537 (7)
C1−0.1667 (5)1.2206 (3)0.2462 (2)0.0806 (11)
H1A−0.22211.20600.28840.121*
H1B−0.23071.26270.21510.121*
H1C−0.07511.26220.25660.121*
C2−0.1239 (4)1.1146 (3)0.21312 (17)0.0589 (8)
C30.0343 (4)1.0375 (2)0.12550 (15)0.0488 (7)
C4−0.0388 (4)1.0074 (3)0.06492 (16)0.0618 (9)
H4−0.12501.04650.04970.074*
C50.0166 (5)0.9191 (3)0.02688 (17)0.0693 (10)
H5−0.03250.8978−0.01400.083*
C60.1450 (4)0.8622 (3)0.04945 (17)0.0631 (9)
H60.18210.80240.02380.076*
C70.2189 (4)0.8933 (2)0.10977 (15)0.0534 (8)
H70.30550.85410.12440.064*
C80.1655 (3)0.9829 (2)0.14935 (14)0.0442 (7)
C90.2499 (3)1.0175 (2)0.21116 (15)0.0451 (7)
C100.3703 (4)1.1884 (2)0.34137 (16)0.0550 (8)
C110.2494 (5)1.2753 (3)0.34728 (19)0.0733 (10)
H11A0.29711.34610.35560.110*
H11B0.18181.25760.38520.110*
H11C0.19131.27840.30480.110*
C120.4469 (4)1.0077 (2)0.28773 (15)0.0518 (7)
H120.55211.03630.28270.062*
C130.4419 (3)0.9151 (2)0.34025 (15)0.0443 (7)
C140.3338 (4)0.9088 (3)0.39249 (16)0.0534 (8)
H140.26170.96540.39750.064*
C150.3307 (4)0.8198 (3)0.43733 (16)0.0562 (8)
H150.25700.81770.47240.067*
C160.4350 (3)0.7333 (2)0.43137 (15)0.0463 (7)
C170.5437 (4)0.7399 (3)0.37835 (17)0.0568 (8)
H170.61460.68260.37280.068*
C180.5483 (4)0.8292 (2)0.33416 (16)0.0557 (8)
H180.62340.83250.29970.067*
C190.4308 (3)0.6360 (2)0.47964 (15)0.0486 (7)
C200.4008 (4)0.6501 (3)0.54999 (17)0.0651 (9)
H200.38190.72100.56730.078*
C210.3985 (5)0.5602 (3)0.5946 (2)0.0803 (12)
H210.37950.57080.64180.096*
C220.4242 (5)0.4550 (3)0.5693 (2)0.0804 (12)
H220.41920.39420.59910.096*
C230.4573 (5)0.4395 (3)0.5002 (2)0.0758 (11)
H230.47780.36850.48340.091*
C240.4601 (4)0.5292 (3)0.45577 (18)0.0610 (8)
H240.48190.51810.40890.073*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0657 (14)0.0503 (12)0.0552 (12)0.0078 (10)0.0035 (11)0.0030 (10)
O20.103 (2)0.0775 (17)0.0877 (18)−0.0177 (17)0.0411 (16)−0.0123 (16)
O30.0576 (13)0.0552 (12)0.0492 (11)0.0090 (10)0.0011 (10)−0.0022 (10)
O40.0828 (18)0.0671 (15)0.0619 (14)−0.0174 (13)−0.0126 (14)−0.0039 (12)
N10.0569 (16)0.0432 (14)0.0538 (15)−0.0015 (12)−0.0060 (13)−0.0069 (13)
N20.0579 (16)0.0417 (13)0.0614 (15)0.0022 (12)−0.0096 (14)−0.0074 (13)
C10.080 (3)0.080 (3)0.082 (3)0.029 (2)−0.003 (2)−0.010 (2)
C20.0554 (19)0.067 (2)0.0539 (19)0.0090 (17)0.0042 (17)−0.0071 (18)
C30.0570 (18)0.0457 (16)0.0438 (16)−0.0027 (15)0.0071 (15)0.0039 (14)
C40.0587 (19)0.077 (2)0.0496 (19)−0.0057 (19)0.0016 (17)0.0002 (17)
C50.072 (2)0.088 (3)0.0487 (19)−0.020 (2)0.0041 (18)−0.0086 (19)
C60.074 (2)0.061 (2)0.055 (2)−0.0131 (19)0.0136 (19)−0.0187 (17)
C70.0576 (19)0.0507 (18)0.0518 (18)−0.0051 (16)0.0093 (16)−0.0033 (15)
C80.0528 (16)0.0371 (14)0.0429 (16)−0.0075 (13)0.0058 (14)0.0042 (13)
C90.0511 (16)0.0368 (15)0.0474 (17)0.0009 (13)0.0030 (14)0.0021 (14)
C100.077 (2)0.0436 (17)0.0445 (17)−0.0122 (17)−0.0019 (18)0.0036 (14)
C110.101 (3)0.0514 (19)0.067 (2)0.003 (2)0.000 (2)−0.0150 (18)
C120.0507 (16)0.0515 (18)0.0532 (18)−0.0041 (15)−0.0030 (15)−0.0049 (15)
C130.0403 (15)0.0447 (15)0.0480 (16)−0.0029 (13)−0.0015 (14)−0.0043 (14)
C140.0498 (18)0.0476 (18)0.063 (2)0.0096 (15)0.0021 (16)0.0006 (16)
C150.0501 (17)0.0585 (19)0.0600 (19)0.0033 (16)0.0147 (16)0.0026 (17)
C160.0420 (16)0.0461 (16)0.0507 (17)−0.0021 (14)0.0002 (15)−0.0069 (14)
C170.0542 (18)0.0513 (18)0.0651 (19)0.0118 (16)0.0066 (17)−0.0032 (16)
C180.0538 (18)0.0588 (18)0.0546 (18)0.0054 (16)0.0115 (16)0.0020 (16)
C190.0398 (16)0.0527 (18)0.0534 (18)0.0000 (14)−0.0006 (14)−0.0025 (15)
C200.074 (2)0.061 (2)0.059 (2)0.0033 (18)0.0058 (19)−0.0022 (18)
C210.092 (3)0.087 (3)0.062 (2)0.006 (2)0.008 (2)0.012 (2)
C220.081 (3)0.076 (3)0.085 (3)0.007 (2)0.012 (2)0.030 (2)
C230.076 (2)0.057 (2)0.094 (3)0.0040 (19)0.012 (2)0.012 (2)
C240.062 (2)0.0540 (19)0.067 (2)0.0000 (18)0.0093 (18)−0.0013 (17)

Geometric parameters (Å, °)

O1—C21.365 (4)C11—H11B0.9600
O1—C31.401 (3)C11—H11C0.9600
O2—C21.183 (4)C12—C131.503 (4)
O3—C91.356 (4)C12—H120.9800
O3—C121.456 (3)C13—C141.376 (4)
O4—C101.230 (4)C13—C181.390 (4)
N1—C91.283 (3)C14—C151.374 (4)
N1—N21.402 (3)C14—H140.9300
N2—C101.355 (4)C15—C161.384 (4)
N2—C121.465 (4)C15—H150.9300
C1—C21.472 (4)C16—C171.391 (4)
C1—H1A0.9600C16—C191.494 (4)
C1—H1B0.9600C17—C181.370 (4)
C1—H1C0.9600C17—H170.9300
C3—C41.374 (4)C18—H180.9300
C3—C81.392 (4)C19—C201.387 (4)
C4—C51.377 (5)C19—C241.387 (4)
C4—H40.9300C20—C211.381 (5)
C5—C61.377 (5)C20—H200.9300
C5—H50.9300C21—C221.374 (5)
C6—C71.376 (4)C21—H210.9300
C6—H60.9300C22—C231.371 (5)
C7—C81.398 (4)C22—H220.9300
C7—H70.9300C23—C241.377 (5)
C8—C91.456 (4)C23—H230.9300
C10—C111.485 (5)C24—H240.9300
C11—H11A0.9600
C2—O1—C3117.3 (2)H11B—C11—H11C109.5
C9—O3—C12106.9 (2)O3—C12—N2100.2 (2)
C9—N1—N2105.1 (2)O3—C12—C13109.7 (2)
C10—N2—N1123.6 (3)N2—C12—C13114.4 (2)
C10—N2—C12124.4 (3)O3—C12—H12110.7
N1—N2—C12110.4 (2)N2—C12—H12110.7
C2—C1—H1A109.5C13—C12—H12110.7
C2—C1—H1B109.5C14—C13—C18118.2 (3)
H1A—C1—H1B109.5C14—C13—C12123.4 (3)
C2—C1—H1C109.5C18—C13—C12118.3 (3)
H1A—C1—H1C109.5C15—C14—C13120.9 (3)
H1B—C1—H1C109.5C15—C14—H14119.5
O2—C2—O1121.9 (3)C13—C14—H14119.5
O2—C2—C1127.3 (3)C14—C15—C16121.4 (3)
O1—C2—C1110.8 (3)C14—C15—H15119.3
C4—C3—C8122.1 (3)C16—C15—H15119.3
C4—C3—O1117.6 (3)C15—C16—C17117.4 (3)
C8—C3—O1120.1 (3)C15—C16—C19121.5 (3)
C3—C4—C5119.5 (3)C17—C16—C19121.1 (3)
C3—C4—H4120.3C18—C17—C16121.3 (3)
C5—C4—H4120.3C18—C17—H17119.4
C4—C5—C6119.9 (3)C16—C17—H17119.4
C4—C5—H5120.1C17—C18—C13120.7 (3)
C6—C5—H5120.1C17—C18—H18119.6
C7—C6—C5120.5 (3)C13—C18—H18119.6
C7—C6—H6119.8C20—C19—C24118.0 (3)
C5—C6—H6119.8C20—C19—C16120.9 (3)
C6—C7—C8120.9 (3)C24—C19—C16121.0 (3)
C6—C7—H7119.6C21—C20—C19120.8 (3)
C8—C7—H7119.6C21—C20—H20119.6
C3—C8—C7117.1 (3)C19—C20—H20119.6
C3—C8—C9123.0 (3)C22—C21—C20119.9 (3)
C7—C8—C9119.9 (3)C22—C21—H21120.1
N1—C9—O3115.8 (3)C20—C21—H21120.1
N1—C9—C8128.2 (3)C23—C22—C21120.2 (3)
O3—C9—C8115.9 (2)C23—C22—H22119.9
O4—C10—N2118.5 (3)C21—C22—H22119.9
O4—C10—C11124.0 (3)C22—C23—C24119.8 (3)
N2—C10—C11117.5 (3)C22—C23—H23120.1
C10—C11—H11A109.5C24—C23—H23120.1
C10—C11—H11B109.5C23—C24—C19121.1 (3)
H11A—C11—H11B109.5C23—C24—H24119.4
C10—C11—H11C109.5C19—C24—H24119.4
H11A—C11—H11C109.5
C9—N1—N2—C10158.3 (3)C10—N2—C12—O3−154.2 (3)
C9—N1—N2—C12−8.2 (3)N1—N2—C12—O312.1 (3)
C3—O1—C2—O2−1.7 (4)C10—N2—C12—C1388.5 (3)
C3—O1—C2—C1178.1 (3)N1—N2—C12—C13−105.2 (3)
C2—O1—C3—C495.3 (3)O3—C12—C13—C14−104.7 (3)
C2—O1—C3—C8−89.4 (3)N2—C12—C13—C147.0 (4)
C8—C3—C4—C51.4 (5)O3—C12—C13—C1872.7 (3)
O1—C3—C4—C5176.6 (3)N2—C12—C13—C18−175.6 (3)
C3—C4—C5—C6−0.5 (5)C18—C13—C14—C15−0.1 (4)
C4—C5—C6—C7−0.2 (5)C12—C13—C14—C15177.3 (3)
C5—C6—C7—C80.0 (5)C13—C14—C15—C16−0.5 (5)
C4—C3—C8—C7−1.6 (4)C14—C15—C16—C170.3 (4)
O1—C3—C8—C7−176.6 (2)C14—C15—C16—C19−179.4 (3)
C4—C3—C8—C9176.3 (3)C15—C16—C17—C180.6 (4)
O1—C3—C8—C91.3 (4)C19—C16—C17—C18−179.7 (3)
C6—C7—C8—C30.9 (4)C16—C17—C18—C13−1.3 (5)
C6—C7—C8—C9−177.1 (3)C14—C13—C18—C171.0 (4)
N2—N1—C9—O30.1 (3)C12—C13—C18—C17−176.5 (3)
N2—N1—C9—C8−175.7 (3)C15—C16—C19—C20−39.6 (4)
C12—O3—C9—N17.9 (3)C17—C16—C19—C20140.8 (3)
C12—O3—C9—C8−175.8 (2)C15—C16—C19—C24141.8 (3)
C3—C8—C9—N16.3 (4)C17—C16—C19—C24−37.8 (4)
C7—C8—C9—N1−175.9 (3)C24—C19—C20—C21−0.7 (5)
C3—C8—C9—O3−169.5 (2)C16—C19—C20—C21−179.3 (3)
C7—C8—C9—O38.3 (4)C19—C20—C21—C22−0.8 (6)
N1—N2—C10—O4−168.8 (3)C20—C21—C22—C232.2 (7)
C12—N2—C10—O4−4.3 (4)C21—C22—C23—C24−2.0 (6)
N1—N2—C10—C1112.9 (4)C22—C23—C24—C190.4 (6)
C12—N2—C10—C11177.4 (3)C20—C19—C24—C230.9 (5)
C9—O3—C12—N2−11.5 (3)C16—C19—C24—C23179.6 (3)
C9—O3—C12—C13109.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2264).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • He, D.-H. & Zhu, Y.-C. (2008). Acta Cryst. E64, o1443. [PMC free article] [PubMed]
  • Jin, L.-H., Chen, J., Song, B.-A., Chen, Z., Yang, S., Li, Q.-Z., Hu, D.-Y. & Xu, R.-Q. (2006). Bioorg. Med. Chem. Lett.16, 5036–5041. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Somogyi, L., Czugler, M. & Sohar, P. (1992). Tetrahedron, 48, 9355–9362.
  • Song, Q.-B., Zhang, J. & Tiekink, E. R. T. (2006). Acta Cryst. E62, o4115–o4117.
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography