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

Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536810009621

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o878

doi:10.1107/S1600536810009621

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

Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 March 2010; accepted 14 March 2010; online 20 March 2010)

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 ); Somogyi et al. (1992 ); Song et al. (2006 ); He & Zhu (2008 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₄
M_r = 400.42
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.00
2029 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

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.

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

Crystal data top

C₂₄H₂₀N₂O₄	F(000) = 840
M_r = 400.42	D_x = 1.326 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2292 reflections
a = 8.6750 (11) Å	θ = 2.6–19.9°
b = 12.0279 (14) Å	µ = 0.09 mm⁻¹
c = 19.221 (2) Å	T = 293 K
V = 2005.6 (4) Å³	Prism, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART APEX diffractometer	1534 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −10→10
16090 measured reflections	k = −14→14
2029 independent reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0598P)² + 0.076P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2029 reflections	Δρ_max = 0.11 e Å⁻³
274 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (18)

Crystal data top

C₂₄H₂₀N₂O₄	V = 2005.6 (4) Å³
M_r = 400.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.6750 (11) Å	µ = 0.09 mm⁻¹
b = 12.0279 (14) Å	T = 293 K
c = 19.221 (2) Å	0.30 × 0.20 × 0.10 mm

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.00	Δρ_max = 0.11 e Å⁻³
2029 reflections	Δρ_min = −0.13 e Å⁻³
274 parameters

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

	x	y	z	U_iso*/U_eq
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)
O3	0.3885 (2)	0.96800 (17)	0.22120 (10)	0.0540 (5)
O4	0.4949 (3)	1.19201 (19)	0.37185 (12)	0.0706 (7)
N1	0.2135 (3)	1.09315 (19)	0.25521 (13)	0.0513 (6)
N2	0.3385 (3)	1.09851 (19)	0.30133 (13)	0.0537 (7)
C1	−0.1667 (5)	1.2206 (3)	0.2462 (2)	0.0806 (11)
H1A	−0.2221	1.2060	0.2884	0.121*
H1B	−0.2307	1.2627	0.2151	0.121*
H1C	−0.0751	1.2622	0.2566	0.121*
C2	−0.1239 (4)	1.1146 (3)	0.21312 (17)	0.0589 (8)
C3	0.0343 (4)	1.0375 (2)	0.12550 (15)	0.0488 (7)
C4	−0.0388 (4)	1.0074 (3)	0.06492 (16)	0.0618 (9)
H4	−0.1250	1.0465	0.0497	0.074*
C5	0.0166 (5)	0.9191 (3)	0.02688 (17)	0.0693 (10)
H5	−0.0325	0.8978	−0.0140	0.083*
C6	0.1450 (4)	0.8622 (3)	0.04945 (17)	0.0631 (9)
H6	0.1821	0.8024	0.0238	0.076*
C7	0.2189 (4)	0.8933 (2)	0.10977 (15)	0.0534 (8)
H7	0.3055	0.8541	0.1244	0.064*
C8	0.1655 (3)	0.9829 (2)	0.14935 (14)	0.0442 (7)
C9	0.2499 (3)	1.0175 (2)	0.21116 (15)	0.0451 (7)
C10	0.3703 (4)	1.1884 (2)	0.34137 (16)	0.0550 (8)
C11	0.2494 (5)	1.2753 (3)	0.34728 (19)	0.0733 (10)
H11A	0.2971	1.3461	0.3556	0.110*
H11B	0.1818	1.2576	0.3852	0.110*
H11C	0.1913	1.2784	0.3048	0.110*
C12	0.4469 (4)	1.0077 (2)	0.28773 (15)	0.0518 (7)
H12	0.5521	1.0363	0.2827	0.062*
C13	0.4419 (3)	0.9151 (2)	0.34025 (15)	0.0443 (7)
C14	0.3338 (4)	0.9088 (3)	0.39249 (16)	0.0534 (8)
H14	0.2617	0.9654	0.3975	0.064*
C15	0.3307 (4)	0.8198 (3)	0.43733 (16)	0.0562 (8)
H15	0.2570	0.8177	0.4724	0.067*
C16	0.4350 (3)	0.7333 (2)	0.43137 (15)	0.0463 (7)
C17	0.5437 (4)	0.7399 (3)	0.37835 (17)	0.0568 (8)
H17	0.6146	0.6826	0.3728	0.068*
C18	0.5483 (4)	0.8292 (2)	0.33416 (16)	0.0557 (8)
H18	0.6234	0.8325	0.2997	0.067*
C19	0.4308 (3)	0.6360 (2)	0.47964 (15)	0.0486 (7)
C20	0.4008 (4)	0.6501 (3)	0.54999 (17)	0.0651 (9)
H20	0.3819	0.7210	0.5673	0.078*
C21	0.3985 (5)	0.5602 (3)	0.5946 (2)	0.0803 (12)
H21	0.3795	0.5708	0.6418	0.096*
C22	0.4242 (5)	0.4550 (3)	0.5693 (2)	0.0804 (12)
H22	0.4192	0.3942	0.5991	0.096*
C23	0.4573 (5)	0.4395 (3)	0.5002 (2)	0.0758 (11)
H23	0.4778	0.3685	0.4834	0.091*
C24	0.4601 (4)	0.5292 (3)	0.45577 (18)	0.0610 (8)
H24	0.4819	0.5181	0.4089	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0657 (14)	0.0503 (12)	0.0552 (12)	0.0078 (10)	0.0035 (11)	0.0030 (10)
O2	0.103 (2)	0.0775 (17)	0.0877 (18)	−0.0177 (17)	0.0411 (16)	−0.0123 (16)
O3	0.0576 (13)	0.0552 (12)	0.0492 (11)	0.0090 (10)	0.0011 (10)	−0.0022 (10)
O4	0.0828 (18)	0.0671 (15)	0.0619 (14)	−0.0174 (13)	−0.0126 (14)	−0.0039 (12)
N1	0.0569 (16)	0.0432 (14)	0.0538 (15)	−0.0015 (12)	−0.0060 (13)	−0.0069 (13)
N2	0.0579 (16)	0.0417 (13)	0.0614 (15)	0.0022 (12)	−0.0096 (14)	−0.0074 (13)
C1	0.080 (3)	0.080 (3)	0.082 (3)	0.029 (2)	−0.003 (2)	−0.010 (2)
C2	0.0554 (19)	0.067 (2)	0.0539 (19)	0.0090 (17)	0.0042 (17)	−0.0071 (18)
C3	0.0570 (18)	0.0457 (16)	0.0438 (16)	−0.0027 (15)	0.0071 (15)	0.0039 (14)
C4	0.0587 (19)	0.077 (2)	0.0496 (19)	−0.0057 (19)	0.0016 (17)	0.0002 (17)
C5	0.072 (2)	0.088 (3)	0.0487 (19)	−0.020 (2)	0.0041 (18)	−0.0086 (19)
C6	0.074 (2)	0.061 (2)	0.055 (2)	−0.0131 (19)	0.0136 (19)	−0.0187 (17)
C7	0.0576 (19)	0.0507 (18)	0.0518 (18)	−0.0051 (16)	0.0093 (16)	−0.0033 (15)
C8	0.0528 (16)	0.0371 (14)	0.0429 (16)	−0.0075 (13)	0.0058 (14)	0.0042 (13)
C9	0.0511 (16)	0.0368 (15)	0.0474 (17)	0.0009 (13)	0.0030 (14)	0.0021 (14)
C10	0.077 (2)	0.0436 (17)	0.0445 (17)	−0.0122 (17)	−0.0019 (18)	0.0036 (14)
C11	0.101 (3)	0.0514 (19)	0.067 (2)	0.003 (2)	0.000 (2)	−0.0150 (18)
C12	0.0507 (16)	0.0515 (18)	0.0532 (18)	−0.0041 (15)	−0.0030 (15)	−0.0049 (15)
C13	0.0403 (15)	0.0447 (15)	0.0480 (16)	−0.0029 (13)	−0.0015 (14)	−0.0043 (14)
C14	0.0498 (18)	0.0476 (18)	0.063 (2)	0.0096 (15)	0.0021 (16)	0.0006 (16)
C15	0.0501 (17)	0.0585 (19)	0.0600 (19)	0.0033 (16)	0.0147 (16)	0.0026 (17)
C16	0.0420 (16)	0.0461 (16)	0.0507 (17)	−0.0021 (14)	0.0002 (15)	−0.0069 (14)
C17	0.0542 (18)	0.0513 (18)	0.0651 (19)	0.0118 (16)	0.0066 (17)	−0.0032 (16)
C18	0.0538 (18)	0.0588 (18)	0.0546 (18)	0.0054 (16)	0.0115 (16)	0.0020 (16)
C19	0.0398 (16)	0.0527 (18)	0.0534 (18)	0.0000 (14)	−0.0006 (14)	−0.0025 (15)
C20	0.074 (2)	0.061 (2)	0.059 (2)	0.0033 (18)	0.0058 (19)	−0.0022 (18)
C21	0.092 (3)	0.087 (3)	0.062 (2)	0.006 (2)	0.008 (2)	0.012 (2)
C22	0.081 (3)	0.076 (3)	0.085 (3)	0.007 (2)	0.012 (2)	0.030 (2)
C23	0.076 (2)	0.057 (2)	0.094 (3)	0.0040 (19)	0.012 (2)	0.012 (2)
C24	0.062 (2)	0.0540 (19)	0.067 (2)	0.0000 (18)	0.0093 (18)	−0.0013 (17)

Geometric parameters (Å, º) top

O1—C2	1.365 (4)	C11—H11B	0.9600
O1—C3	1.401 (3)	C11—H11C	0.9600
O2—C2	1.183 (4)	C12—C13	1.503 (4)
O3—C9	1.356 (4)	C12—H12	0.9800
O3—C12	1.456 (3)	C13—C14	1.376 (4)
O4—C10	1.230 (4)	C13—C18	1.390 (4)
N1—C9	1.283 (3)	C14—C15	1.374 (4)
N1—N2	1.402 (3)	C14—H14	0.9300
N2—C10	1.355 (4)	C15—C16	1.384 (4)
N2—C12	1.465 (4)	C15—H15	0.9300
C1—C2	1.472 (4)	C16—C17	1.391 (4)
C1—H1A	0.9600	C16—C19	1.494 (4)
C1—H1B	0.9600	C17—C18	1.370 (4)
C1—H1C	0.9600	C17—H17	0.9300
C3—C4	1.374 (4)	C18—H18	0.9300
C3—C8	1.392 (4)	C19—C20	1.387 (4)
C4—C5	1.377 (5)	C19—C24	1.387 (4)
C4—H4	0.9300	C20—C21	1.381 (5)
C5—C6	1.377 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.374 (5)
C6—C7	1.376 (4)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.371 (5)
C7—C8	1.398 (4)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.377 (5)
C8—C9	1.456 (4)	C23—H23	0.9300
C10—C11	1.485 (5)	C24—H24	0.9300
C11—H11A	0.9600

C2—O1—C3	117.3 (2)	H11B—C11—H11C	109.5
C9—O3—C12	106.9 (2)	O3—C12—N2	100.2 (2)
C9—N1—N2	105.1 (2)	O3—C12—C13	109.7 (2)
C10—N2—N1	123.6 (3)	N2—C12—C13	114.4 (2)
C10—N2—C12	124.4 (3)	O3—C12—H12	110.7
N1—N2—C12	110.4 (2)	N2—C12—H12	110.7
C2—C1—H1A	109.5	C13—C12—H12	110.7
C2—C1—H1B	109.5	C14—C13—C18	118.2 (3)
H1A—C1—H1B	109.5	C14—C13—C12	123.4 (3)
C2—C1—H1C	109.5	C18—C13—C12	118.3 (3)
H1A—C1—H1C	109.5	C15—C14—C13	120.9 (3)
H1B—C1—H1C	109.5	C15—C14—H14	119.5
O2—C2—O1	121.9 (3)	C13—C14—H14	119.5
O2—C2—C1	127.3 (3)	C14—C15—C16	121.4 (3)
O1—C2—C1	110.8 (3)	C14—C15—H15	119.3
C4—C3—C8	122.1 (3)	C16—C15—H15	119.3
C4—C3—O1	117.6 (3)	C15—C16—C17	117.4 (3)
C8—C3—O1	120.1 (3)	C15—C16—C19	121.5 (3)
C3—C4—C5	119.5 (3)	C17—C16—C19	121.1 (3)
C3—C4—H4	120.3	C18—C17—C16	121.3 (3)
C5—C4—H4	120.3	C18—C17—H17	119.4
C4—C5—C6	119.9 (3)	C16—C17—H17	119.4
C4—C5—H5	120.1	C17—C18—C13	120.7 (3)
C6—C5—H5	120.1	C17—C18—H18	119.6
C7—C6—C5	120.5 (3)	C13—C18—H18	119.6
C7—C6—H6	119.8	C20—C19—C24	118.0 (3)
C5—C6—H6	119.8	C20—C19—C16	120.9 (3)
C6—C7—C8	120.9 (3)	C24—C19—C16	121.0 (3)
C6—C7—H7	119.6	C21—C20—C19	120.8 (3)
C8—C7—H7	119.6	C21—C20—H20	119.6
C3—C8—C7	117.1 (3)	C19—C20—H20	119.6
C3—C8—C9	123.0 (3)	C22—C21—C20	119.9 (3)
C7—C8—C9	119.9 (3)	C22—C21—H21	120.1
N1—C9—O3	115.8 (3)	C20—C21—H21	120.1
N1—C9—C8	128.2 (3)	C23—C22—C21	120.2 (3)
O3—C9—C8	115.9 (2)	C23—C22—H22	119.9
O4—C10—N2	118.5 (3)	C21—C22—H22	119.9
O4—C10—C11	124.0 (3)	C22—C23—C24	119.8 (3)
N2—C10—C11	117.5 (3)	C22—C23—H23	120.1
C10—C11—H11A	109.5	C24—C23—H23	120.1
C10—C11—H11B	109.5	C23—C24—C19	121.1 (3)
H11A—C11—H11B	109.5	C23—C24—H24	119.4
C10—C11—H11C	109.5	C19—C24—H24	119.4
H11A—C11—H11C	109.5

C9—N1—N2—C10	158.3 (3)	C10—N2—C12—O3	−154.2 (3)
C9—N1—N2—C12	−8.2 (3)	N1—N2—C12—O3	12.1 (3)
C3—O1—C2—O2	−1.7 (4)	C10—N2—C12—C13	88.5 (3)
C3—O1—C2—C1	178.1 (3)	N1—N2—C12—C13	−105.2 (3)
C2—O1—C3—C4	95.3 (3)	O3—C12—C13—C14	−104.7 (3)
C2—O1—C3—C8	−89.4 (3)	N2—C12—C13—C14	7.0 (4)
C8—C3—C4—C5	1.4 (5)	O3—C12—C13—C18	72.7 (3)
O1—C3—C4—C5	176.6 (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—C15	177.3 (3)
C5—C6—C7—C8	0.0 (5)	C13—C14—C15—C16	−0.5 (5)
C4—C3—C8—C7	−1.6 (4)	C14—C15—C16—C17	0.3 (4)
O1—C3—C8—C7	−176.6 (2)	C14—C15—C16—C19	−179.4 (3)
C4—C3—C8—C9	176.3 (3)	C15—C16—C17—C18	0.6 (4)
O1—C3—C8—C9	1.3 (4)	C19—C16—C17—C18	−179.7 (3)
C6—C7—C8—C3	0.9 (4)	C16—C17—C18—C13	−1.3 (5)
C6—C7—C8—C9	−177.1 (3)	C14—C13—C18—C17	1.0 (4)
N2—N1—C9—O3	0.1 (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—N1	7.9 (3)	C17—C16—C19—C20	140.8 (3)
C12—O3—C9—C8	−175.8 (2)	C15—C16—C19—C24	141.8 (3)
C3—C8—C9—N1	6.3 (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—O3	8.3 (4)	C19—C20—C21—C22	−0.8 (6)
N1—N2—C10—O4	−168.8 (3)	C20—C21—C22—C23	2.2 (7)
C12—N2—C10—O4	−4.3 (4)	C21—C22—C23—C24	−2.0 (6)
N1—N2—C10—C11	12.9 (4)	C22—C23—C24—C19	0.4 (6)
C12—N2—C10—C11	177.4 (3)	C20—C19—C24—C23	0.9 (5)
C9—O3—C12—N2	−11.5 (3)	C16—C19—C24—C23	179.6 (3)
C9—O3—C12—C13	109.3 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₄
M_r	400.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.6750 (11), 12.0279 (14), 19.221 (2)
V (Å³)	2005.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16090, 2029, 1534
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.00
No. of reflections	2029
No. of parameters	274
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.13

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
He, D.-H. & Zhu, Y.-C. (2008). Acta Cryst. E64, o1443. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Somogyi, L., Czugler, M. & Sohar, P. (1992). Tetrahedron, 48, 9355–9362. CSD CrossRef CAS Web of Science Google Scholar
Song, Q.-B., Zhang, J. & Tiekink, E. R. T. (2006). Acta Cryst. E62, o4115–o4117. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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Volume 66| Part 4| April 2010| Page o878

doi:10.1107/S1600536810009621

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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