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In the title compound, C9H5Cl3N2O, the dihedral angle between the oxadiazole and benzene rings is 9.0 (2)°. There are intra- and inter­molecular C—H...N inter­actions in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038785/ob2069sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038785/ob2069Isup2.hkl
Contains datablock I

CCDC reference: 624953

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.150
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. O .. 3.18 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C9 H5 Cl3 N2 O
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 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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.

5-chloromethyl-3-(2,4-dichlorophenyl)-1,2,4-oxadiazole top
Crystal data top
C9H5Cl3N2OF(000) = 528
Mr = 263.50Dx = 1.651 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.9010 (16) Åθ = 9–12°
b = 14.987 (3) ŵ = 0.84 mm1
c = 9.7400 (19) ÅT = 293 K
β = 113.20 (3)°Block, colourless
V = 1060.1 (4) Å30.40 × 0.40 × 0.30 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1624 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 26.0°, θmin = 2.7°
ω/2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 018
Tmin = 0.731, Tmax = 0.788l = 1111
2218 measured reflections3 standard reflections every 200 reflections
2068 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2068 reflectionsΔρmax = 0.32 e Å3
137 parametersΔρmin = 0.43 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.062 (7)
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.) 7.86–7.87 (d, 1H), 7.53–7.53(s, 1H), 7.33–7.35 (d,1H),4.75(s,2H)

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
Cl11.30084 (14)0.13305 (8)1.58940 (10)0.0769 (4)
Cl21.19557 (13)0.18437 (7)0.63940 (10)0.0707 (3)
Cl30.97789 (11)0.12352 (5)0.79112 (9)0.0597 (3)
O1.2692 (3)0.19137 (13)1.2556 (2)0.0636 (6)
N11.3665 (3)0.05402 (15)1.2674 (3)0.0454 (6)
N21.1989 (4)0.15913 (18)1.1074 (3)0.0630 (8)
C11.4614 (4)0.1409 (2)1.5042 (3)0.0545 (8)
H1B1.51740.19961.52190.065*
H1C1.55810.09701.54750.065*
C21.3666 (4)0.12516 (19)1.3413 (3)0.0461 (7)
C31.2605 (3)0.07820 (18)1.1210 (3)0.0413 (6)
C41.2314 (3)0.01518 (18)0.9979 (3)0.0397 (6)
C51.3329 (4)0.06406 (19)1.0319 (3)0.0502 (7)
H5A1.41090.07531.13060.060*
C61.3212 (4)0.1259 (2)0.9245 (4)0.0551 (8)
H6A1.39000.17820.95010.066*
C71.2055 (4)0.1092 (2)0.7779 (3)0.0491 (7)
C81.0998 (4)0.0327 (2)0.7394 (3)0.0485 (7)
H8A1.01970.02290.64080.058*
C91.1141 (3)0.02907 (19)0.8485 (3)0.0422 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0658 (6)0.1112 (8)0.0527 (5)0.0126 (5)0.0224 (4)0.0011 (5)
Cl20.0693 (6)0.0802 (6)0.0645 (6)0.0047 (4)0.0284 (4)0.0242 (4)
Cl30.0599 (5)0.0527 (5)0.0524 (5)0.0072 (3)0.0070 (4)0.0095 (3)
O0.0836 (16)0.0437 (12)0.0484 (12)0.0060 (11)0.0097 (11)0.0028 (9)
N10.0444 (13)0.0443 (13)0.0410 (12)0.0014 (10)0.0098 (10)0.0005 (10)
N20.085 (2)0.0468 (15)0.0440 (14)0.0069 (13)0.0110 (13)0.0007 (11)
C10.0524 (18)0.0553 (18)0.0467 (17)0.0075 (14)0.0099 (13)0.0071 (13)
C20.0418 (15)0.0444 (15)0.0471 (16)0.0057 (12)0.0122 (12)0.0006 (12)
C30.0366 (13)0.0416 (15)0.0427 (14)0.0027 (11)0.0126 (11)0.0062 (11)
C40.0341 (13)0.0450 (14)0.0384 (13)0.0054 (11)0.0126 (10)0.0030 (11)
C50.0480 (16)0.0547 (17)0.0406 (15)0.0062 (13)0.0096 (12)0.0019 (12)
C60.0477 (17)0.0524 (17)0.062 (2)0.0065 (13)0.0176 (15)0.0050 (14)
C70.0438 (16)0.0564 (17)0.0497 (16)0.0076 (13)0.0213 (13)0.0104 (13)
C80.0440 (15)0.0621 (18)0.0379 (14)0.0081 (13)0.0144 (12)0.0015 (13)
C90.0357 (13)0.0466 (15)0.0441 (14)0.0041 (11)0.0154 (11)0.0049 (12)
Geometric parameters (Å, º) top
Cl1—C11.773 (4)C3—C41.472 (4)
Cl2—C71.736 (3)C4—C51.398 (4)
Cl3—C91.732 (3)C4—C91.399 (4)
O—C21.329 (4)C5—C61.373 (4)
O—N21.412 (3)C5—H5A0.9300
N1—C21.286 (4)C6—C71.382 (4)
N1—C31.387 (3)C6—H6A0.9300
N2—C31.294 (4)C7—C81.380 (4)
C1—C21.482 (4)C8—C91.380 (4)
C1—H1B0.9700C8—H8A0.9300
C1—H1C0.9700
C2—O—N2106.5 (2)C9—C4—C3125.4 (3)
C2—N1—C3103.0 (2)C6—C5—C4122.2 (3)
C3—N2—O103.6 (2)C6—C5—H5A118.9
C2—C1—Cl1109.7 (2)C4—C5—H5A118.9
C2—C1—H1B109.7C5—C6—C7118.9 (3)
Cl1—C1—H1B109.7C5—C6—H6A120.5
C2—C1—H1C109.7C7—C6—H6A120.5
Cl1—C1—H1C109.7C8—C7—C6121.0 (3)
H1B—C1—H1C108.2C8—C7—Cl2119.4 (2)
N1—C2—O113.3 (3)C6—C7—Cl2119.6 (2)
N1—C2—C1128.3 (3)C9—C8—C7119.4 (3)
O—C2—C1118.5 (3)C9—C8—H8A120.3
N2—C3—N1113.6 (2)C7—C8—H8A120.3
N2—C3—C4125.9 (2)C8—C9—C4121.4 (3)
N1—C3—C4120.5 (2)C8—C9—Cl3116.6 (2)
C5—C4—C9117.2 (3)C4—C9—Cl3122.0 (2)
C5—C4—C3117.4 (2)
C2—O—N2—C30.3 (3)N1—C3—C4—C9173.7 (2)
C3—N1—C2—O0.7 (3)C9—C4—C5—C60.7 (4)
C3—N1—C2—C1178.5 (3)C3—C4—C5—C6177.6 (3)
N2—O—C2—N10.7 (4)C4—C5—C6—C70.1 (5)
N2—O—C2—C1178.6 (3)C5—C6—C7—C81.4 (5)
Cl1—C1—C2—N1102.1 (3)C5—C6—C7—Cl2177.5 (2)
Cl1—C1—C2—O78.7 (3)C6—C7—C8—C91.9 (4)
O—N2—C3—N10.1 (3)Cl2—C7—C8—C9177.0 (2)
O—N2—C3—C4178.0 (2)C7—C8—C9—C41.0 (4)
C2—N1—C3—N20.5 (3)C7—C8—C9—Cl3179.7 (2)
C2—N1—C3—C4177.8 (2)C5—C4—C9—C80.3 (4)
N2—C3—C4—C5169.9 (3)C3—C4—C9—C8177.9 (2)
N1—C3—C4—C58.1 (4)C5—C4—C9—Cl3179.0 (2)
N2—C3—C4—C98.2 (4)C3—C4—C9—Cl32.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···N2i0.972.513.468 (4)171
C5—H5A···N10.932.452.825 (4)104
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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