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The title compound, C15H18Cl2N2O3, is an effective herbicide. The oxadiazo­lone ring is not coplanar with the benzene ring. Pairs of mol­ecules form centrosymmetric dimers via weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010129/bt2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010129/bt2034Isup2.hkl
Contains datablock I

CCDC reference: 604988

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.087
  • Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 - C12 .. 8.14 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 .. 15.07 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C13
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C7 .. 5.39 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.48 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: CrystalStructure.

3-(2,4-Dichloro-5-isopropyloxyphenyl)-5-tert-butyl-1,3,4-oxadiazol-2-one top
Crystal data top
C15H18Cl2N2O3F(000) = 720.00
Mr = 345.22Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 11821 reflections
a = 9.700 (4) Åθ = 3.0–27.6°
b = 11.068 (4) ŵ = 0.38 mm1
c = 16.514 (8) ÅT = 298 K
β = 94.135 (19)°Platelet, colourless
V = 1768.2 (13) Å30.47 × 0.40 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2237 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.033
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1112
Tmin = 0.830, Tmax = 0.927k = 1414
16776 measured reflectionsl = 2121
4042 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0002Fo2 + 1.1σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.087Δρmax = 0.28 e Å3
S = 1.01Δρmin = 0.39 e Å3
4042 reflectionsExtinction correction: Larson (1970)
200 parametersExtinction coefficient: 680 (31)
H-atom parameters constrained
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.61000 (5)0.34219 (4)0.59774 (3)0.08260 (17)
Cl20.52794 (6)0.80583 (5)0.67346 (4)0.1122 (2)
O10.94279 (12)0.34897 (12)0.56869 (8)0.0812 (4)
O20.93898 (11)0.31647 (9)0.43213 (6)0.0631 (3)
O30.68748 (14)0.85931 (11)0.53821 (8)0.0896 (4)
N10.79123 (13)0.44406 (12)0.47346 (8)0.0596 (4)
N20.77606 (13)0.44566 (12)0.38864 (8)0.0611 (4)
C10.72188 (14)0.53029 (13)0.52013 (10)0.0551 (4)
C20.64082 (14)0.49367 (13)0.58086 (10)0.0587 (4)
C30.58093 (16)0.57965 (16)0.62739 (11)0.0666 (5)
C40.59967 (17)0.69976 (16)0.61198 (11)0.0677 (5)
C50.67629 (17)0.73834 (14)0.54864 (10)0.0645 (5)
C60.73817 (14)0.65100 (14)0.50390 (10)0.0596 (5)
C70.89451 (18)0.36929 (14)0.50152 (12)0.0612 (5)
C80.86450 (17)0.36838 (13)0.36800 (10)0.0571 (4)
C90.89543 (19)0.32991 (14)0.28464 (10)0.0663 (5)
C100.8707 (2)0.19493 (16)0.27599 (12)0.0889 (7)
C111.0471 (2)0.3585 (2)0.27323 (13)0.1142 (9)
C120.8001 (2)0.3975 (2)0.22321 (12)0.1054 (8)
C130.7536 (2)0.90625 (17)0.47009 (12)0.0838 (7)
C140.6630 (2)0.8937 (2)0.39353 (14)0.1058 (8)
C150.7839 (3)1.0369 (2)0.49061 (16)0.1531 (12)
H30.52770.55600.66930.080*
H60.79180.67420.46210.072*
H130.84060.86300.46450.101*
H1010.77860.17620.28980.107*
H1020.93610.15220.31180.107*
H1030.88170.17100.22100.107*
H1111.10530.30580.30680.137*
H1121.06510.34680.21740.137*
H1131.06620.44090.28830.137*
H1210.81800.37230.16930.126*
H1220.81640.48280.22870.126*
H1230.70570.38020.23280.126*
H1410.65650.81000.37840.127*
H1420.70170.93880.35100.127*
H1430.57250.92420.40200.127*
H1510.82711.07440.44660.184*
H1520.69921.07800.49930.184*
H1530.84481.04120.53900.184*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0747 (3)0.0763 (3)0.0964 (4)0.0096 (2)0.0033 (2)0.0183 (2)
Cl20.1382 (5)0.1007 (4)0.1061 (4)0.0235 (3)0.0653 (4)0.0047 (3)
O10.0749 (8)0.1199 (10)0.0480 (8)0.0260 (7)0.0006 (6)0.0086 (7)
O20.0670 (7)0.0722 (7)0.0501 (7)0.0091 (5)0.0050 (5)0.0027 (5)
O30.1286 (11)0.0656 (7)0.0801 (9)0.0047 (7)0.0447 (8)0.0019 (6)
N10.0655 (8)0.0683 (8)0.0441 (8)0.0081 (6)0.0019 (6)0.0002 (6)
N20.0690 (8)0.0662 (8)0.0470 (8)0.0012 (6)0.0022 (6)0.0018 (6)
C10.0487 (8)0.0661 (9)0.0497 (9)0.0023 (7)0.0018 (7)0.0010 (7)
C20.0479 (8)0.0693 (10)0.0581 (10)0.0039 (7)0.0017 (8)0.0086 (8)
C30.0555 (10)0.0837 (11)0.0621 (11)0.0019 (8)0.0148 (8)0.0107 (9)
C40.0634 (10)0.0796 (11)0.0619 (11)0.0083 (8)0.0162 (9)0.0006 (9)
C50.0689 (10)0.0668 (10)0.0592 (11)0.0015 (8)0.0140 (9)0.0024 (8)
C60.0595 (10)0.0709 (10)0.0493 (10)0.0005 (7)0.0099 (8)0.0037 (8)
C70.0609 (10)0.0713 (10)0.0514 (11)0.0057 (8)0.0044 (8)0.0027 (9)
C80.0635 (10)0.0591 (9)0.0484 (10)0.0053 (8)0.0009 (8)0.0041 (8)
C90.0787 (11)0.0749 (11)0.0461 (10)0.0056 (9)0.0093 (9)0.0014 (8)
C100.1224 (17)0.0827 (12)0.0633 (13)0.0054 (11)0.0187 (12)0.0129 (10)
C110.1025 (16)0.162 (2)0.0817 (16)0.0277 (15)0.0336 (13)0.0008 (14)
C120.157 (2)0.1063 (15)0.0519 (12)0.0141 (14)0.0004 (13)0.0037 (11)
C130.1141 (16)0.0715 (11)0.0684 (13)0.0140 (11)0.0238 (12)0.0021 (10)
C140.1310 (19)0.0863 (14)0.1028 (18)0.0037 (13)0.0271 (15)0.0119 (13)
C150.269 (3)0.0887 (16)0.108 (2)0.0652 (19)0.060 (2)0.0177 (14)
Geometric parameters (Å, º) top
Cl1—C21.7291 (16)C13—C141.494 (3)
Cl2—C41.7306 (19)C13—C151.509 (2)
O1—C71.194 (2)C3—H30.930
O2—C71.383 (2)C6—H60.930
O2—C81.3650 (19)C10—H1010.960
O3—C51.355 (2)C10—H1020.960
O3—C131.432 (2)C10—H1030.960
N1—N21.3980 (18)C11—H1110.960
N1—C11.426 (2)C11—H1120.960
N1—C71.355 (2)C11—H1130.960
N2—C81.275 (2)C12—H1210.960
C1—C21.379 (2)C12—H1220.960
C1—C61.374 (2)C12—H1230.960
C2—C31.378 (2)C13—H130.980
C3—C41.368 (2)C14—H1410.960
C4—C51.393 (2)C14—H1420.960
C5—C61.380 (2)C14—H1430.960
C8—C91.492 (2)C15—H1510.960
C9—C101.518 (2)C15—H1520.960
C9—C111.530 (2)C15—H1530.960
C9—C121.520 (2)
O1···N1i3.5562 (18)H102···C11vii3.549
O1···N2i3.5809 (18)H102···H112vii3.415
O1···C6i3.398 (2)H102···H113vii2.863
O1···C10ii3.576 (2)H102···H122vii3.156
O2···C6i3.2519 (17)H102···H142v3.374
N1···O1i3.5562 (18)H102···H151v2.674
N2···O1i3.5809 (18)H103···Cl1iv3.214
N2···C3iii3.465 (2)H103···O1iv2.634
C3···N2iii3.465 (2)H103···C11vii3.526
C6···O1i3.398 (2)H103···H113vii2.602
C6···O2i3.2519 (17)H111···C3i3.402
C6···C7i3.578 (2)H111···C4i3.072
C7···C6i3.578 (2)H111···C5i3.114
C7···C7i3.546 (2)H111···C6i3.409
C10···O1iv3.576 (2)H112···O1iv3.422
Cl1···H101ii3.467H112···C14vii3.358
Cl1···H103ii3.214H112···H13vii3.208
Cl1···H121ii3.280H112···H102viii3.415
Cl1···H123ii3.405H112···H141vii3.252
Cl1···H141iii3.134H112···H142vii2.792
Cl1···H143iii3.438H113···O1i3.319
Cl1···H152v3.484H113···C2i3.519
Cl2···H101iii3.084H113···C10viii3.082
Cl2···H123iii3.503H113···H101viii3.315
Cl2···H143vi3.355H113···H102viii2.863
O1···H6i2.672H113···H103viii2.602
O1···H13i3.223H113···H142vii3.334
O1···H103ii2.634H121···Cl1iv3.280
O1···H112ii3.422H121···O1iv3.243
O1···H113i3.319H121···C15ix3.113
O1···H121ii3.243H121···H152ix3.008
O1···H153v3.560H121···H153ix2.387
O2···H6i3.037H122···H102viii3.156
O2···H13i3.302H122···H153ix3.175
O2···H151v2.906H123···Cl1iv3.405
N2···H3iii3.032H123···Cl2iii3.503
C2···H113i3.519H123···H3iii2.961
C3···H111i3.402H123···H143xii3.406
C4···H111i3.072H141···Cl1iii3.134
C5···H111i3.114H141···H112viii3.252
C6···H111i3.409H142···C10xiii3.543
C7···H6i3.097H142···C11viii3.414
C7···H151v3.437H142···H3ix3.335
C8···H151v3.531H142···H101xiii2.932
C10···H113vii3.082H142···H102xiii3.374
C10···H142v3.543H142···H112viii2.792
C10···H151v3.172H142···H113viii3.334
C11···H102viii3.549H143···Cl1iii3.438
C11···H103viii3.526H143···Cl2vi3.355
C11···H142vii3.414H143···H123xiv3.406
C12···H153ix3.177H143···H152vi3.197
C14···H112viii3.358H151···O2xiii2.906
C15···H121x3.113H151···C7xiii3.437
H3···N2iii3.032H151···C8xiii3.531
H3···H123iii2.961H151···C10xiii3.172
H3···H142x3.335H151···H13xi3.513
H6···O1i2.672H151···H101xiii2.832
H6···O2i3.037H151···H102xiii2.674
H6···C7i3.097H151···H153xi3.423
H13···O1i3.223H152···Cl1xiii3.484
H13···O2i3.302H152···H121x3.008
H13···H112viii3.208H152···H143vi3.197
H13···H151xi3.513H153···O1xiii3.560
H13···H153xi3.234H153···C12x3.177
H101···Cl1iv3.467H153···H13xi3.234
H101···Cl2iii3.084H153···H121x2.387
H101···H113vii3.315H153···H122x3.175
H101···H142v2.932H153···H151xi3.423
H101···H151v2.832H153···H153xi3.481
C7—O2—C8106.60 (12)C4—C3—H3120.0
C5—O3—C13120.18 (14)C1—C6—H6119.5
N2—N1—C1120.90 (12)C5—C6—H6119.5
N2—N1—C7111.85 (13)C9—C10—H101109.5
C1—N1—C7126.16 (14)C9—C10—H102109.5
N1—N2—C8103.60 (12)C9—C10—H103109.5
N1—C1—C2120.83 (13)H101—C10—H102109.5
N1—C1—C6118.69 (14)H101—C10—H103109.5
C2—C1—C6120.48 (14)H102—C10—H103109.5
Cl1—C2—C1121.09 (12)C9—C11—H111109.5
Cl1—C2—C3119.67 (12)C9—C11—H112109.5
C1—C2—C3119.21 (14)C9—C11—H113109.5
C2—C3—C4120.03 (16)H111—C11—H112109.5
Cl2—C4—C3119.05 (14)H111—C11—H113109.5
Cl2—C4—C5119.43 (13)H112—C11—H113109.5
C3—C4—C5121.51 (16)C9—C12—H121109.5
O3—C5—C4116.75 (15)C9—C12—H122109.5
O3—C5—C6125.59 (15)C9—C12—H123109.5
C4—C5—C6117.61 (15)H121—C12—H122109.5
C1—C6—C5121.07 (15)H121—C12—H123109.5
O1—C7—O2124.43 (15)H122—C12—H123109.5
O1—C7—N1131.57 (17)O3—C13—H13109.5
O2—C7—N1104.00 (14)C14—C13—H13109.5
O2—C8—N2113.80 (14)C15—C13—H13109.5
O2—C8—C9117.74 (13)C13—C14—H141109.5
N2—C8—C9128.46 (14)C13—C14—H142109.5
C8—C9—C10109.07 (14)C13—C14—H143109.5
C8—C9—C11108.28 (14)H141—C14—H142109.5
C8—C9—C12108.80 (15)H141—C14—H143109.5
C10—C9—C11109.82 (16)H142—C14—H143109.5
C10—C9—C12109.71 (15)C13—C15—H151109.5
C11—C9—C12111.12 (16)C13—C15—H152109.5
O3—C13—C14111.17 (18)C13—C15—H153109.5
O3—C13—C15105.20 (17)H151—C15—H152109.5
C14—C13—C15111.88 (18)H151—C15—H153109.5
C2—C3—H3120.0H152—C15—H153109.5
C7—O2—C8—N21.53 (17)N1—C1—C2—C3176.79 (13)
C7—O2—C8—C9178.17 (14)N1—C1—C6—C5178.30 (13)
C8—O2—C7—O1176.28 (16)C2—C1—C6—C51.2 (2)
C8—O2—C7—N13.26 (16)C6—C1—C2—Cl1175.72 (11)
C5—O3—C13—C1474.6 (2)C6—C1—C2—C32.7 (2)
C5—O3—C13—C15164.09 (17)Cl1—C2—C3—C4177.02 (12)
C13—O3—C5—C4174.29 (16)C1—C2—C3—C41.4 (2)
C13—O3—C5—C68.2 (2)C2—C3—C4—Cl2177.91 (12)
N2—N1—C1—C2127.14 (15)C2—C3—C4—C51.4 (2)
N2—N1—C1—C653.37 (19)Cl2—C4—C5—O31.3 (2)
C1—N1—N2—C8171.90 (13)Cl2—C4—C5—C6176.46 (12)
N2—N1—C7—O1175.51 (18)C3—C4—C5—O3179.45 (15)
N2—N1—C7—O24.00 (17)C3—C4—C5—C62.8 (2)
C7—N1—N2—C83.12 (17)O3—C5—C6—C1179.04 (14)
C1—N1—C7—O17.4 (3)C4—C5—C6—C11.5 (2)
C1—N1—C7—O2172.06 (13)O2—C8—C9—C1059.71 (19)
C7—N1—C1—C265.8 (2)O2—C8—C9—C1159.76 (19)
C7—N1—C1—C6113.70 (18)O2—C8—C9—C12179.35 (15)
N1—N2—C8—O20.89 (17)N2—C8—C9—C10120.64 (19)
N1—N2—C8—C9179.45 (15)N2—C8—C9—C11119.9 (2)
N1—C1—C2—Cl14.8 (2)N2—C8—C9—C121.0 (2)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x, y+1/2, z1/2; (v) x, y1, z; (vi) x+1, y+2, z+1; (vii) x+2, y1/2, z+1/2; (viii) x+2, y+1/2, z+1/2; (ix) x, y+3/2, z1/2; (x) x, y+3/2, z+1/2; (xi) x+2, y+2, z+1; (xii) x+1, y1/2, z+1/2; (xiii) x, y+1, z; (xiv) x+1, y+1/2, z+1/2.
 

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