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

In the title mol-ecule, C(24)H(20)N(2)O(4), 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 = 400.42

Orthorhombic,

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 ▶); 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 ▶).

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

C24H20N2O4	F(000) = 840
Mr = 400.42	Dx = 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

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

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(Fo2) + (0.0598P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2029 reflections	Δρmax = 0.11 e Å−3
274 parameters	Δρmin = −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)

	x	y	z	Uiso*/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)
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*

	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)

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)