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In the title compound, C10H9ClN2O, the benzene and oxadiazole rings are roughly coplanar. The crystal packing shows weak inter­molecular C—H...N inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056073/kj2072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056073/kj2072Isup2.hkl
Contains datablock I

CCDC reference: 674081

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.057
  • wR factor = 0.182
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 9.71 Cell volume su given = 7.00 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

1,2,4-Oxadiazoles represent an important class of five-membered heterocycles. Some derivatives of 1,2,4-oxadiazoles have intrinsic analgesic (Terashita et al., 2002), antiinflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties and are efficient as agonists [e.g. forangiotensin (Naka et al., 1999) and adhesion agents (Juraszyk et al., 1997)] for different types of receptors, such as the peroxisome proliferator-activated receptor.

The molecular structure of the title compound is shown in Fig. 1. The structure analysis demonstrates that the benzene and oxadiazole rings are roughly coplanar, making a twist angle of only 4.4 (3). The crystal packing shows weak intermolecular C—H···N interactions.

Related literature top

For related literature, see: Juraszyk et al. (1997); Naka & Kubo (1999); Nicolaides et al. (1998); Romero (2001); Terashita et al. (2002).

Experimental top

A solution of chloroacetylchloride (12 mmol) in toluene (10 ml) was added dropwise to a solution of 4-methylbenzamidoxime (10 mmol) in toluene (60 ml). The resulting mixture was refluxed for 6 h. After cooling and filtrating, the crude title compound was gained. The pure title compound was obtained by recrystallizing from a mixture of ethyl acetate (8 ml) and petrolum ether (7.5 ml). Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

All H atoms bonded to C atoms were placed geometrically at the distances of 0.93–0.97 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level.
5-Chloromethyl-3-(4-methylphenyl)-1,2,4-oxadiazole top
Crystal data top
C10H9ClN2OF(000) = 864
Mr = 208.64Dx = 1.387 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 25.462 (5) Åθ = 9–13°
b = 6.4040 (13) ŵ = 0.35 mm1
c = 14.589 (3) ÅT = 293 K
β = 122.83 (3)°Block, colourless
V = 1998.9 (7) Å30.40 × 0.10 × 0.10 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
1259 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω/2θ scansh = 3126
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.873, Tmax = 0.966l = 017
2002 measured reflections3 standard reflections every 200 reflections
1959 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
1959 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C10H9ClN2OV = 1998.9 (7) Å3
Mr = 208.64Z = 8
Monoclinic, C2/cMo Kα radiation
a = 25.462 (5) ŵ = 0.35 mm1
b = 6.4040 (13) ÅT = 293 K
c = 14.589 (3) Å0.40 × 0.10 × 0.10 mm
β = 122.83 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1259 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.041
Tmin = 0.873, Tmax = 0.9663 standard reflections every 200 reflections
2002 measured reflections intensity decay: none
1959 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.182H-atom parameters constrained
S = 1.02Δρmax = 0.28 e Å3
1959 reflectionsΔρmin = 0.31 e Å3
127 parameters
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 7.12–7.15 (m, 2H), 7.36–7.39 (m, 2H), 4.64 (s, 2H), 2.35 (s, 3H).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.02222 (5)0.14389 (18)0.38492 (8)0.0812 (4)
O0.08264 (11)0.5594 (4)0.5539 (2)0.0601 (7)
N10.13240 (13)0.7029 (4)0.5847 (3)0.0609 (8)
N20.16296 (12)0.3737 (4)0.5827 (2)0.0468 (7)
C10.41839 (18)0.8720 (6)0.7058 (3)0.0729 (11)
H1B0.44700.75650.73240.109*
H1C0.43410.97950.76030.109*
H1D0.41410.92620.64070.109*
C20.35583 (15)0.7997 (6)0.6807 (3)0.0523 (8)
C30.34571 (16)0.5951 (5)0.6953 (3)0.0562 (9)
H3A0.37850.50030.72230.067*
C40.28841 (15)0.5270 (5)0.6712 (3)0.0532 (8)
H4A0.28300.38770.68230.064*
C50.23873 (15)0.6639 (5)0.6305 (2)0.0449 (7)
C60.24793 (17)0.8724 (5)0.6149 (3)0.0528 (8)
H6A0.21520.96750.58770.063*
C70.30605 (18)0.9360 (5)0.6403 (3)0.0572 (9)
H7A0.31191.07520.62990.069*
C80.17730 (14)0.5851 (5)0.5989 (2)0.0445 (7)
C90.10588 (16)0.3704 (5)0.5555 (2)0.0470 (8)
C100.06392 (17)0.1880 (5)0.5267 (3)0.0561 (9)
H10A0.03480.21340.54890.067*
H10B0.08840.06520.56500.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0833 (8)0.0822 (8)0.0651 (6)0.0317 (6)0.0317 (5)0.0112 (5)
O0.0480 (13)0.0442 (13)0.0893 (18)0.0034 (11)0.0381 (13)0.0040 (12)
N10.0509 (17)0.0406 (15)0.090 (2)0.0009 (13)0.0376 (16)0.0041 (14)
N20.0492 (16)0.0377 (14)0.0543 (15)0.0016 (12)0.0286 (13)0.0022 (11)
C10.061 (2)0.083 (3)0.077 (3)0.018 (2)0.039 (2)0.009 (2)
C20.052 (2)0.056 (2)0.0490 (18)0.0086 (16)0.0272 (16)0.0069 (15)
C30.0445 (18)0.057 (2)0.060 (2)0.0084 (16)0.0232 (16)0.0049 (16)
C40.0466 (19)0.0419 (18)0.064 (2)0.0008 (15)0.0258 (16)0.0029 (15)
C50.0508 (18)0.0376 (16)0.0449 (16)0.0003 (14)0.0250 (14)0.0000 (13)
C60.059 (2)0.0407 (18)0.060 (2)0.0054 (15)0.0329 (17)0.0006 (15)
C70.069 (2)0.0417 (18)0.071 (2)0.0102 (17)0.0441 (19)0.0065 (16)
C80.0460 (18)0.0393 (17)0.0467 (17)0.0028 (14)0.0241 (14)0.0009 (12)
C90.0516 (19)0.0436 (18)0.0482 (17)0.0025 (14)0.0287 (15)0.0019 (14)
C100.056 (2)0.0485 (19)0.068 (2)0.0053 (16)0.0358 (17)0.0027 (16)
Geometric parameters (Å, º) top
Cl—C101.761 (4)C3—C41.373 (5)
O—C91.342 (4)C3—H3A0.9300
O—N11.426 (4)C4—C51.381 (4)
N1—C81.289 (4)C4—H4A0.9300
N2—C91.282 (4)C5—C61.395 (4)
N2—C81.389 (4)C5—C81.460 (5)
C1—C21.501 (5)C6—C71.378 (5)
C1—H1B0.9600C6—H6A0.9300
C1—H1C0.9600C7—H7A0.9300
C1—H1D0.9600C9—C101.482 (4)
C2—C31.374 (5)C10—H10A0.9700
C2—C71.380 (5)C10—H10B0.9700
C9—O—N1105.5 (2)C6—C5—C8121.7 (3)
C8—N1—O103.5 (3)C7—C6—C5119.3 (3)
C9—N2—C8102.6 (3)C7—C6—H6A120.3
C2—C1—H1B109.5C5—C6—H6A120.3
C2—C1—H1C109.5C6—C7—C2122.1 (3)
H1B—C1—H1C109.5C6—C7—H7A118.9
C2—C1—H1D109.5C2—C7—H7A118.9
H1B—C1—H1D109.5N1—C8—N2114.5 (3)
H1C—C1—H1D109.5N1—C8—C5123.6 (3)
C3—C2—C7117.6 (3)N2—C8—C5121.9 (3)
C3—C2—C1121.3 (3)N2—C9—O113.9 (3)
C7—C2—C1121.1 (3)N2—C9—C10128.5 (3)
C4—C3—C2121.7 (3)O—C9—C10117.6 (3)
C4—C3—H3A119.1C9—C10—Cl110.0 (2)
C2—C3—H3A119.1C9—C10—H10A109.7
C3—C4—C5120.4 (3)Cl—C10—H10A109.7
C3—C4—H4A119.8C9—C10—H10B109.7
C5—C4—H4A119.8Cl—C10—H10B109.7
C4—C5—C6118.8 (3)H10A—C10—H10B108.2
C4—C5—C8119.4 (3)
C9—O—N1—C80.8 (3)C9—N2—C8—N11.2 (4)
C7—C2—C3—C40.1 (5)C9—N2—C8—C5179.3 (3)
C1—C2—C3—C4179.1 (3)C4—C5—C8—N1163.2 (3)
C2—C3—C4—C50.3 (5)C6—C5—C8—N120.5 (5)
C3—C4—C5—C60.3 (5)C4—C5—C8—N216.2 (5)
C3—C4—C5—C8176.1 (3)C6—C5—C8—N2160.1 (3)
C4—C5—C6—C70.1 (5)C8—N2—C9—O0.7 (4)
C8—C5—C6—C7176.3 (3)C8—N2—C9—C10179.5 (3)
C5—C6—C7—C20.1 (5)N1—O—C9—N20.1 (4)
C3—C2—C7—C60.1 (5)N1—O—C9—C10179.8 (3)
C1—C2—C7—C6178.9 (3)N2—C9—C10—Cl91.1 (4)
O—N1—C8—N21.3 (4)O—C9—C10—Cl89.1 (3)
O—N1—C8—C5179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N20.932.582.892 (5)100
C10—H10B···N1i0.972.523.436 (5)157
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC10H9ClN2O
Mr208.64
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)25.462 (5), 6.4040 (13), 14.589 (3)
β (°) 122.83 (3)
V3)1998.9 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.40 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.873, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
2002, 1959, 1259
Rint0.041
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.182, 1.02
No. of reflections1959
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N1i0.97002.52003.436 (5)157.00
Symmetry code: (i) x, y1, z.
 

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