2-[3-Acetyl-5-(2-chloro-3-pyrid-yl)-2-methyl-2,3-dihydro-1,3,4-oxadiazol-2-yl]-4-fluoro-phenyl acetate.

In the title compound, C(18)H(15)ClFN(3)O(4), the dihedral angle between the substituted pyridine ring and the oxadiazo-line ring is 9.73 (19)° and the acyl group is coplanar with the oxadiazo-line ring [O-C-N-C torsion angle = -2.1 (3)°]. Furthermore, the substituted benzene ring is almost orthogonal with the oxadiazo-line ring, the dihedral angle between them being 87.56 (18)°.

Related literature

For background to 1,3,4-oxadiazo­line derivatives and related structures, see: Song et al. (2006a ▶,b ▶); Pan et al. (2007 ▶). For the pharmacological properties of 2,5-disubstituted 1,3,4-oxa­diazo­lines, see: Chimirri et al. (1994 ▶, 1996 ▶); Dogan et al. (1998 ▶).

Experimental

Crystal data

C18H15ClFN3O4

M = 391.78

Monoclinic,

a = 10.120 (2) Å

b = 13.900 (3) Å

c = 13.320 (3) Å

β = 102.14 (3)°

V = 1831.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.971, T max = 0.981

9882 measured reflections

3403 independent reflections

2394 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.00

3403 reflections

248 parameters

H-atom parameters not refined

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015323/tk2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015323/tk2411Isup2.hkl

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

C18H15ClFN3O4	F(000) = 808
Mr = 391.78	Dx = 1.421 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3403 reflections
a = 10.120 (2) Å	θ = 2.1–25.5°
b = 13.900 (3) Å	µ = 0.25 mm−1
c = 13.320 (3) Å	T = 293 K
β = 102.14 (3)°	Block, colorless
V = 1831.8 (6) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→7
Tmin = 0.971, Tmax = 0.981	k = −16→16
9882 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.06P)2 + 0.3383P] where P = (Fo2 + 2Fc2)/3
3403 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
C1	0.0490 (3)	0.1369 (2)	0.5790 (2)	0.0842 (8)
H1A	−0.0049	0.1943	0.5694	0.126*
H1B	0.0010	0.0859	0.5383	0.126*
H1C	0.1328	0.1485	0.5580	0.126*
C2	0.0772 (2)	0.10902 (17)	0.6890 (2)	0.0686 (6)
C3	0.1358 (2)	−0.02657 (15)	0.79837 (16)	0.0566 (5)
C4	0.0293 (3)	−0.04387 (16)	0.8454 (2)	0.0702 (7)
H4	−0.0576	−0.0247	0.8140	0.084*
C5	0.0520 (3)	−0.08956 (18)	0.9390 (2)	0.0778 (7)
H5	−0.0187	−0.1021	0.9718	0.093*
C6	0.1815 (3)	−0.11600 (17)	0.98264 (17)	0.0729 (7)
C7	0.2892 (3)	−0.09887 (15)	0.93740 (16)	0.0627 (6)
H7	0.3758	−0.1177	0.9699	0.075*
C8	0.2675 (2)	−0.05317 (14)	0.84270 (15)	0.0523 (5)
C9	0.3835 (2)	−0.03837 (14)	0.78801 (14)	0.0517 (5)
C10	0.5212 (2)	−0.07353 (16)	0.84381 (18)	0.0655 (6)
H10A	0.5183	−0.1419	0.8534	0.098*
H10B	0.5454	−0.0425	0.9095	0.098*
H10C	0.5872	−0.0585	0.8039	0.098*
C11	0.4183 (3)	0.23549 (16)	0.76258 (19)	0.0731 (7)
H11A	0.3303	0.2645	0.7478	0.110*
H11B	0.4494	0.2268	0.6999	0.110*
H11C	0.4801	0.2765	0.8080	0.110*
C12	0.4110 (2)	0.14036 (15)	0.81247 (16)	0.0551 (5)
C13	0.35464 (19)	−0.02406 (16)	0.61505 (14)	0.0512 (5)
C14	0.3289 (2)	−0.06543 (17)	0.51150 (15)	0.0561 (5)
C15	0.3246 (2)	−0.16524 (19)	0.50291 (18)	0.0692 (6)
H15	0.3420	−0.2032	0.5617	0.083*
C16	0.2944 (2)	−0.2080 (2)	0.4075 (2)	0.0806 (8)
H16	0.2913	−0.2746	0.4009	0.097*
C17	0.2691 (3)	−0.1500 (3)	0.3232 (2)	0.0896 (9)
H17	0.2472	−0.1791	0.2590	0.107*
C18	0.3038 (2)	−0.0137 (2)	0.41987 (16)	0.0655 (6)
Cl1	0.30866 (7)	0.11042 (5)	0.41760 (5)	0.0845 (3)
F1	0.2064 (2)	−0.16130 (13)	1.07494 (10)	0.1092 (6)
N1	0.37927 (17)	0.06330 (13)	0.64394 (12)	0.0543 (4)
N2	0.39054 (17)	0.06139 (12)	0.75037 (12)	0.0525 (4)
N3	0.2739 (2)	−0.0537 (2)	0.32705 (14)	0.0793 (6)
O1	0.10784 (15)	0.01308 (10)	0.69914 (11)	0.0612 (4)
O2	0.42063 (17)	0.13026 (11)	0.90474 (11)	0.0697 (5)
O3	0.0761 (2)	0.15939 (13)	0.76138 (16)	0.0960 (6)
O4	0.34983 (15)	−0.08897 (10)	0.69061 (10)	0.0569 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0707 (17)	0.0814 (18)	0.097 (2)	0.0185 (13)	0.0106 (14)	0.0250 (15)
C2	0.0516 (13)	0.0587 (15)	0.0921 (19)	0.0046 (11)	0.0072 (12)	−0.0006 (14)
C3	0.0683 (15)	0.0453 (11)	0.0562 (12)	−0.0010 (10)	0.0132 (11)	−0.0100 (9)
C4	0.0750 (16)	0.0595 (15)	0.0802 (17)	−0.0053 (12)	0.0258 (13)	−0.0181 (12)
C5	0.098 (2)	0.0677 (16)	0.0785 (18)	−0.0171 (15)	0.0424 (16)	−0.0228 (14)
C6	0.116 (2)	0.0610 (15)	0.0452 (13)	−0.0158 (14)	0.0260 (14)	−0.0094 (10)
C7	0.0875 (17)	0.0523 (13)	0.0470 (12)	−0.0097 (11)	0.0112 (12)	−0.0046 (10)
C8	0.0686 (14)	0.0409 (11)	0.0462 (11)	−0.0038 (9)	0.0097 (10)	−0.0070 (8)
C9	0.0636 (13)	0.0448 (11)	0.0434 (11)	0.0005 (9)	0.0036 (9)	0.0021 (8)
C10	0.0662 (14)	0.0631 (14)	0.0630 (14)	0.0084 (11)	0.0038 (11)	0.0152 (11)
C11	0.0900 (18)	0.0493 (13)	0.0749 (16)	−0.0044 (12)	0.0058 (13)	0.0103 (11)
C12	0.0573 (13)	0.0493 (12)	0.0531 (13)	0.0000 (9)	−0.0012 (10)	0.0032 (9)
C13	0.0449 (11)	0.0609 (13)	0.0457 (11)	0.0075 (10)	0.0048 (9)	0.0037 (10)
C14	0.0425 (11)	0.0771 (15)	0.0474 (12)	0.0085 (10)	0.0065 (9)	−0.0007 (10)
C15	0.0611 (14)	0.0862 (18)	0.0574 (14)	0.0141 (12)	0.0058 (11)	−0.0118 (12)
C16	0.0746 (17)	0.095 (2)	0.0675 (17)	0.0166 (14)	0.0046 (13)	−0.0188 (14)
C17	0.0727 (18)	0.132 (3)	0.0597 (17)	0.0181 (18)	0.0046 (13)	−0.0288 (17)
C18	0.0463 (12)	0.0983 (18)	0.0509 (13)	0.0108 (11)	0.0077 (10)	0.0046 (12)
Cl1	0.0910 (5)	0.0999 (5)	0.0607 (4)	0.0095 (4)	0.0117 (3)	0.0222 (3)
F1	0.1671 (18)	0.1102 (13)	0.0567 (9)	−0.0254 (11)	0.0381 (10)	0.0077 (8)
N1	0.0541 (10)	0.0628 (12)	0.0431 (9)	0.0031 (8)	0.0033 (8)	0.0088 (8)
N2	0.0628 (11)	0.0474 (10)	0.0429 (9)	0.0000 (8)	0.0011 (8)	0.0065 (7)
N3	0.0658 (13)	0.123 (2)	0.0473 (12)	0.0129 (13)	0.0071 (9)	−0.0021 (11)
O1	0.0643 (9)	0.0546 (9)	0.0614 (9)	0.0060 (7)	0.0060 (7)	−0.0009 (7)
O2	0.0934 (12)	0.0583 (9)	0.0497 (9)	−0.0047 (8)	−0.0023 (8)	0.0010 (7)
O3	0.1075 (15)	0.0635 (11)	0.1116 (16)	0.0128 (10)	0.0107 (12)	−0.0142 (11)
O4	0.0735 (10)	0.0501 (8)	0.0461 (8)	0.0030 (7)	0.0102 (7)	−0.0016 (6)

C1—C2	1.484 (4)	C10—H10B	0.9600
C1—H1A	0.9600	C10—H10C	0.9600
C1—H1B	0.9600	C11—C12	1.489 (3)
C1—H1C	0.9600	C11—H11A	0.9600
C2—O3	1.194 (3)	C11—H11B	0.9600
C2—O1	1.369 (3)	C11—H11C	0.9600
C3—C4	1.377 (3)	C12—O2	1.220 (2)
C3—C8	1.390 (3)	C12—N2	1.364 (3)
C3—O1	1.405 (2)	C13—N1	1.282 (3)
C4—C5	1.375 (3)	C13—O4	1.360 (2)
C4—H4	0.9300	C13—C14	1.466 (3)
C5—C6	1.367 (4)	C14—C15	1.392 (3)
C5—H5	0.9300	C14—C18	1.393 (3)
C6—F1	1.357 (3)	C15—C16	1.377 (3)
C6—C7	1.373 (3)	C15—H15	0.9300
C7—C8	1.388 (3)	C16—C17	1.362 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.520 (3)	C17—N3	1.340 (4)
C9—O4	1.452 (2)	C17—H17	0.9300
C9—N2	1.481 (2)	C18—N3	1.331 (3)
C9—C10	1.516 (3)	C18—Cl1	1.727 (3)
C10—H10A	0.9600	N1—N2	1.398 (2)
C2—C1—H1A	109.5	H10A—C10—H10C	109.5
C2—C1—H1B	109.5	H10B—C10—H10C	109.5
H1A—C1—H1B	109.5	C12—C11—H11A	109.5
C2—C1—H1C	109.5	C12—C11—H11B	109.5
H1A—C1—H1C	109.5	H11A—C11—H11B	109.5
H1B—C1—H1C	109.5	C12—C11—H11C	109.5
O3—C2—O1	122.1 (2)	H11A—C11—H11C	109.5
O3—C2—C1	127.7 (2)	H11B—C11—H11C	109.5
O1—C2—C1	110.2 (2)	O2—C12—N2	119.22 (19)
C4—C3—C8	122.2 (2)	O2—C12—C11	123.4 (2)
C4—C3—O1	118.3 (2)	N2—C12—C11	117.36 (19)
C8—C3—O1	119.31 (19)	N1—C13—O4	116.17 (17)
C5—C4—C3	119.7 (3)	N1—C13—C14	129.68 (19)
C5—C4—H4	120.1	O4—C13—C14	114.15 (18)
C3—C4—H4	120.1	C15—C14—C18	116.4 (2)
C6—C5—C4	118.2 (2)	C15—C14—C13	117.68 (19)
C6—C5—H5	120.9	C18—C14—C13	125.8 (2)
C4—C5—H5	120.9	C16—C15—C14	120.2 (2)
F1—C6—C5	119.3 (3)	C16—C15—H15	119.9
F1—C6—C7	117.7 (3)	C14—C15—H15	119.9
C5—C6—C7	123.0 (2)	C17—C16—C15	118.2 (3)
C6—C7—C8	119.4 (2)	C17—C16—H16	120.9
C6—C7—H7	120.3	C15—C16—H16	120.9
C8—C7—H7	120.3	N3—C17—C16	124.1 (2)
C7—C8—C3	117.5 (2)	N3—C17—H17	118.0
C7—C8—C9	120.5 (2)	C16—C17—H17	118.0
C3—C8—C9	121.92 (18)	N3—C18—C14	124.3 (3)
O4—C9—N2	99.78 (14)	N3—C18—Cl1	113.72 (19)
O4—C9—C10	107.50 (17)	C14—C18—Cl1	122.02 (18)
N2—C9—C10	111.29 (17)	C13—N1—N2	104.80 (16)
O4—C9—C8	107.64 (16)	C12—N2—N1	124.70 (17)
N2—C9—C8	112.70 (16)	C12—N2—C9	124.06 (16)
C10—C9—C8	116.38 (17)	N1—N2—C9	111.19 (15)
C9—C10—H10A	109.5	C18—N3—C17	116.8 (2)
C9—C10—H10B	109.5	C2—O1—C3	118.16 (18)
H10A—C10—H10B	109.5	C13—O4—C9	107.56 (15)
C9—C10—H10C	109.5
C8—C3—C4—C5	−0.5 (3)	C15—C14—C18—Cl1	−178.79 (16)
O1—C3—C4—C5	174.88 (19)	C13—C14—C18—Cl1	3.5 (3)
C3—C4—C5—C6	0.3 (3)	O4—C13—N1—N2	−1.3 (2)
C4—C5—C6—F1	−179.9 (2)	C14—C13—N1—N2	177.94 (19)
C4—C5—C6—C7	0.1 (4)	O2—C12—N2—N1	−179.27 (18)
F1—C6—C7—C8	179.65 (18)	C11—C12—N2—N1	1.6 (3)
C5—C6—C7—C8	−0.4 (3)	O2—C12—N2—C9	−2.1 (3)
C6—C7—C8—C3	0.2 (3)	C11—C12—N2—C9	178.74 (19)
C6—C7—C8—C9	−176.51 (19)	C13—N1—N2—C12	−177.06 (19)
C4—C3—C8—C7	0.2 (3)	C13—N1—N2—C9	5.5 (2)
O1—C3—C8—C7	−175.12 (17)	O4—C9—N2—C12	175.46 (18)
C4—C3—C8—C9	176.90 (19)	C10—C9—N2—C12	−71.3 (3)
O1—C3—C8—C9	1.5 (3)	C8—C9—N2—C12	61.5 (2)
C7—C8—C9—O4	119.08 (18)	O4—C9—N2—N1	−7.0 (2)
C3—C8—C9—O4	−57.5 (2)	C10—C9—N2—N1	106.21 (19)
C7—C8—C9—N2	−131.88 (18)	C8—C9—N2—N1	−120.95 (17)
C3—C8—C9—N2	51.6 (2)	C14—C18—N3—C17	−0.5 (3)
C7—C8—C9—C10	−1.6 (3)	Cl1—C18—N3—C17	179.67 (18)
C3—C8—C9—C10	−178.13 (18)	C16—C17—N3—C18	−0.8 (4)
N1—C13—C14—C15	170.8 (2)	O3—C2—O1—C3	1.4 (3)
O4—C13—C14—C15	−10.0 (3)	C1—C2—O1—C3	−179.18 (19)
N1—C13—C14—C18	−11.5 (3)	C4—C3—O1—C2	75.7 (2)
O4—C13—C14—C18	167.70 (19)	C8—C3—O1—C2	−108.7 (2)
C18—C14—C15—C16	−1.0 (3)	N1—C13—O4—C9	−3.4 (2)
C13—C14—C15—C16	176.9 (2)	C14—C13—O4—C9	177.29 (16)
C14—C15—C16—C17	−0.1 (4)	N2—C9—O4—C13	5.97 (19)
C15—C16—C17—N3	1.1 (4)	C10—C9—O4—C13	−110.18 (18)
C15—C14—C18—N3	1.4 (3)	C8—C9—O4—C13	123.72 (16)
C13—C14—C18—N3	−176.3 (2)