Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048064/im2037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048064/im2037Isup2.hkl |
CCDC reference: 669129
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.173
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5 .. N1 .. 99.30 Deg.
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 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 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
For related literature, see: Nicolaides et al. (1998); Romero (2001); Terashita et al. (2002).
A solution of chloroacetylchloride (16 mmol) in toluene (10 ml) was added dropwise to a solution of 3,5- (Dimethoxyl)benzamidoxime (14 mmol) in toluene (60 ml). The resulting mixture was refluxed for 6 h, then concentrated under reduced pressure to afford crude compound(I). Pure compound (I) was obtained by recrystallization from a mixture of ethyl acetate (15 ml) and light petrolum (b.p. 60–90°C, 7.5 ml). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution. 1H NMR (CDCl3, δ, p.p.m.): 6.55–6.56 (m, 2H), 6.23–6.25 (m, 1H), 4.64 (s, 2H), 3.77 (s, 6H).
All H atoms bonded to the C atoms were placed geometrically at distances of 0.93–0.97 Å and included in the refinement using an riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.
1,2,4-Oxadiazoles are an important class of five-membered heterocyclic compounds. Some derivatives of 1,2,4-oxadiazoles showed intrinsic analgesic (Terashita et al., 2002), antiinflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties. We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1, where the dashed lines indicate close C—H···N contacts which most probably are caused by the coplanar arrangement of the phenyl group and the oxadiazole system (Table 1). The other bond lengths and angles are of expected values (cf. Supplementary Material).
For related literature, see: Nicolaides et al. (1998); Romero (2001); Terashita et al. (2002).
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).
Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level. Dashed lines indicate C—H···N interactions. |
C11H11ClN2O3 | Z = 2 |
Mr = 254.67 | F(000) = 264 |
Triclinic, P1 | Dx = 1.473 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.861 (2) Å | Cell parameters from 25 reflections |
b = 8.502 (2) Å | θ = 9–13° |
c = 9.537 (2) Å | µ = 0.33 mm−1 |
α = 80.72 (3)° | T = 293 K |
β = 73.90 (3)° | Block, colourless |
γ = 70.09 (3)° | 0.40 × 0.20 × 0.20 mm |
V = 574.2 (2) Å3 |
Enraf–Nonius CAD-4 diffractometer | 1589 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 26.0°, θmin = 2.2° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→10 |
Tmin = 0.879, Tmax = 0.937 | l = 0→11 |
2422 measured reflections | 3 standard reflections every 200 reflections |
2249 independent reflections | intensity decay: none |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.05P)2 + P] where P = (Fo2 + 2Fc2)/3 |
2249 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C11H11ClN2O3 | γ = 70.09 (3)° |
Mr = 254.67 | V = 574.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.861 (2) Å | Mo Kα radiation |
b = 8.502 (2) Å | µ = 0.33 mm−1 |
c = 9.537 (2) Å | T = 293 K |
α = 80.72 (3)° | 0.40 × 0.20 × 0.20 mm |
β = 73.90 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1589 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.031 |
Tmin = 0.879, Tmax = 0.937 | 3 standard reflections every 200 reflections |
2422 measured reflections | intensity decay: none |
2249 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.31 e Å−3 |
2249 reflections | Δρmin = −0.34 e Å−3 |
154 parameters |
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 | ||
Cl | 0.3102 (2) | 0.49956 (16) | 0.15386 (12) | 0.0816 (5) | |
O1 | 0.3892 (4) | 0.1611 (3) | 0.3056 (3) | 0.0548 (7) | |
O2 | −0.1673 (4) | −0.1007 (4) | 0.9489 (3) | 0.0684 (9) | |
O3 | 0.3152 (4) | −0.5222 (3) | 0.6710 (3) | 0.0578 (7) | |
N1 | 0.3733 (5) | 0.0065 (4) | 0.3778 (4) | 0.0538 (8) | |
N2 | 0.1641 (4) | 0.2229 (4) | 0.5042 (3) | 0.0451 (7) | |
C1 | 0.2542 (6) | 0.4563 (5) | 0.3446 (4) | 0.0577 (10) | |
H1B | 0.3402 | 0.4823 | 0.3861 | 0.069* | |
H1C | 0.1297 | 0.5283 | 0.3852 | 0.069* | |
C2 | 0.2623 (5) | 0.2789 (5) | 0.3874 (4) | 0.0448 (8) | |
C3 | 0.2402 (5) | 0.0511 (4) | 0.4938 (4) | 0.0414 (8) | |
C4 | 0.1792 (5) | −0.0743 (5) | 0.6045 (4) | 0.0425 (8) | |
C5 | 0.2710 (5) | −0.2428 (4) | 0.5881 (4) | 0.0444 (8) | |
H5A | 0.3678 | −0.2777 | 0.5065 | 0.053* | |
C6 | 0.2172 (5) | −0.3588 (4) | 0.6944 (4) | 0.0446 (8) | |
C7 | 0.0694 (5) | −0.3066 (5) | 0.8134 (4) | 0.0492 (9) | |
H7A | 0.0335 | −0.3858 | 0.8841 | 0.059* | |
C8 | −0.0273 (5) | −0.1346 (5) | 0.8283 (4) | 0.0478 (9) | |
C9 | 0.0298 (5) | −0.0180 (5) | 0.7237 (4) | 0.0469 (9) | |
H9A | −0.0304 | 0.0961 | 0.7325 | 0.056* | |
C10 | −0.2766 (6) | 0.0704 (5) | 0.9669 (5) | 0.0689 (12) | |
H10A | −0.3717 | 0.0780 | 1.0563 | 0.103* | |
H10B | −0.3335 | 0.1144 | 0.8859 | 0.103* | |
H10C | −0.1981 | 0.1342 | 0.9707 | 0.103* | |
C11 | 0.2735 (6) | −0.6468 (5) | 0.7836 (4) | 0.0576 (10) | |
H11A | 0.3507 | −0.7563 | 0.7535 | 0.086* | |
H11B | 0.1447 | −0.6389 | 0.8003 | 0.086* | |
H11C | 0.2970 | −0.6286 | 0.8722 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.1243 (11) | 0.0765 (8) | 0.0512 (6) | −0.0560 (8) | −0.0131 (6) | 0.0155 (5) |
O1 | 0.0591 (16) | 0.0518 (16) | 0.0486 (15) | −0.0255 (13) | 0.0038 (12) | −0.0016 (12) |
O2 | 0.083 (2) | 0.0516 (17) | 0.0531 (17) | −0.0204 (15) | 0.0089 (15) | −0.0010 (13) |
O3 | 0.0741 (19) | 0.0412 (15) | 0.0502 (15) | −0.0192 (13) | −0.0034 (13) | 0.0006 (12) |
N1 | 0.060 (2) | 0.0454 (18) | 0.0511 (19) | −0.0211 (15) | −0.0039 (16) | 0.0029 (14) |
N2 | 0.0504 (18) | 0.0469 (18) | 0.0389 (16) | −0.0189 (14) | −0.0094 (13) | −0.0001 (13) |
C1 | 0.070 (3) | 0.051 (2) | 0.051 (2) | −0.024 (2) | −0.012 (2) | 0.0041 (18) |
C2 | 0.047 (2) | 0.051 (2) | 0.0414 (19) | −0.0225 (17) | −0.0130 (16) | 0.0006 (16) |
C3 | 0.0431 (19) | 0.045 (2) | 0.0422 (19) | −0.0196 (15) | −0.0157 (15) | 0.0013 (15) |
C4 | 0.0450 (19) | 0.051 (2) | 0.0402 (18) | −0.0238 (16) | −0.0155 (15) | 0.0024 (15) |
C5 | 0.047 (2) | 0.050 (2) | 0.0375 (18) | −0.0187 (16) | −0.0077 (15) | −0.0029 (15) |
C6 | 0.055 (2) | 0.042 (2) | 0.0414 (19) | −0.0190 (16) | −0.0166 (16) | 0.0010 (15) |
C7 | 0.063 (2) | 0.046 (2) | 0.042 (2) | −0.0247 (18) | −0.0132 (18) | 0.0063 (16) |
C8 | 0.056 (2) | 0.050 (2) | 0.0375 (19) | −0.0200 (17) | −0.0089 (16) | −0.0004 (15) |
C9 | 0.058 (2) | 0.0422 (19) | 0.046 (2) | −0.0206 (17) | −0.0179 (17) | 0.0043 (15) |
C10 | 0.076 (3) | 0.058 (3) | 0.061 (3) | −0.019 (2) | −0.002 (2) | −0.006 (2) |
C11 | 0.072 (3) | 0.041 (2) | 0.052 (2) | −0.0175 (19) | −0.006 (2) | 0.0038 (17) |
Cl—C1 | 1.757 (4) | C4—C9 | 1.397 (5) |
O1—C2 | 1.322 (4) | C5—C6 | 1.380 (5) |
O1—N1 | 1.411 (4) | C5—H5A | 0.9300 |
O2—C8 | 1.343 (4) | C6—C7 | 1.384 (5) |
O2—C10 | 1.426 (5) | C7—C8 | 1.410 (5) |
O3—C6 | 1.360 (4) | C7—H7A | 0.9300 |
O3—C11 | 1.434 (4) | C8—C9 | 1.384 (5) |
N1—C3 | 1.298 (5) | C9—H9A | 0.9300 |
N2—C2 | 1.290 (4) | C10—H10A | 0.9600 |
N2—C3 | 1.386 (4) | C10—H10B | 0.9600 |
C1—C2 | 1.482 (5) | C10—H10C | 0.9600 |
C1—H1B | 0.9700 | C11—H11A | 0.9600 |
C1—H1C | 0.9700 | C11—H11B | 0.9600 |
C3—C4 | 1.478 (5) | C11—H11C | 0.9600 |
C4—C5 | 1.380 (5) | ||
C2—O1—N1 | 106.2 (3) | O3—C6—C7 | 124.1 (3) |
C8—O2—C10 | 117.5 (3) | C5—C6—C7 | 120.3 (3) |
C6—O3—C11 | 117.6 (3) | C6—C7—C8 | 120.6 (3) |
C3—N1—O1 | 103.1 (3) | C6—C7—H7A | 119.7 |
C2—N2—C3 | 101.7 (3) | C8—C7—H7A | 119.7 |
C2—C1—Cl | 112.7 (3) | O2—C8—C9 | 126.2 (4) |
C2—C1—H1B | 109.1 | O2—C8—C7 | 114.7 (3) |
Cl—C1—H1B | 109.1 | C9—C8—C7 | 119.1 (3) |
C2—C1—H1C | 109.1 | C8—C9—C4 | 119.1 (3) |
Cl—C1—H1C | 109.1 | C8—C9—H9A | 120.5 |
H1B—C1—H1C | 107.8 | C4—C9—H9A | 120.5 |
N2—C2—O1 | 114.5 (3) | O2—C10—H10A | 109.5 |
N2—C2—C1 | 126.6 (3) | O2—C10—H10B | 109.5 |
O1—C2—C1 | 118.8 (3) | H10A—C10—H10B | 109.5 |
N1—C3—N2 | 114.5 (3) | O2—C10—H10C | 109.5 |
N1—C3—C4 | 121.6 (3) | H10A—C10—H10C | 109.5 |
N2—C3—C4 | 123.9 (3) | H10B—C10—H10C | 109.5 |
C5—C4—C9 | 121.8 (3) | O3—C11—H11A | 109.5 |
C5—C4—C3 | 119.4 (3) | O3—C11—H11B | 109.5 |
C9—C4—C3 | 118.7 (3) | H11A—C11—H11B | 109.5 |
C6—C5—C4 | 119.1 (3) | O3—C11—H11C | 109.5 |
C6—C5—H5A | 120.5 | H11A—C11—H11C | 109.5 |
C4—C5—H5A | 120.5 | H11B—C11—H11C | 109.5 |
O3—C6—C5 | 115.6 (3) | ||
C2—O1—N1—C3 | −0.4 (4) | C3—C4—C5—C6 | 177.8 (3) |
C3—N2—C2—O1 | 0.6 (4) | C11—O3—C6—C5 | 175.6 (3) |
C3—N2—C2—C1 | −174.9 (4) | C11—O3—C6—C7 | −6.0 (5) |
N1—O1—C2—N2 | −0.1 (4) | C4—C5—C6—O3 | −179.5 (3) |
N1—O1—C2—C1 | 175.7 (3) | C4—C5—C6—C7 | 2.0 (5) |
Cl—C1—C2—N2 | −150.1 (3) | O3—C6—C7—C8 | −178.9 (3) |
Cl—C1—C2—O1 | 34.6 (5) | C5—C6—C7—C8 | −0.5 (6) |
O1—N1—C3—N2 | 0.8 (4) | C10—O2—C8—C9 | 4.6 (6) |
O1—N1—C3—C4 | −178.7 (3) | C10—O2—C8—C7 | −177.0 (4) |
C2—N2—C3—N1 | −0.9 (4) | C6—C7—C8—O2 | −179.7 (4) |
C2—N2—C3—C4 | 178.6 (3) | C6—C7—C8—C9 | −1.2 (6) |
N1—C3—C4—C5 | 3.0 (5) | O2—C8—C9—C4 | 179.7 (4) |
N2—C3—C4—C5 | −176.4 (3) | C7—C8—C9—C4 | 1.3 (5) |
N1—C3—C4—C9 | −177.3 (4) | C5—C4—C9—C8 | 0.2 (5) |
N2—C3—C4—C9 | 3.3 (5) | C3—C4—C9—C8 | −179.5 (3) |
C9—C4—C5—C6 | −1.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N2 | 0.93 | 2.60 | 2.925 (5) | 101 |
C5—H5A···N1 | 0.93 | 2.54 | 2.838 (5) | 99 |
Experimental details
Crystal data | |
Chemical formula | C11H11ClN2O3 |
Mr | 254.67 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.861 (2), 8.502 (2), 9.537 (2) |
α, β, γ (°) | 80.72 (3), 73.90 (3), 70.09 (3) |
V (Å3) | 574.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.879, 0.937 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2422, 2249, 1589 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.173, 1.08 |
No. of reflections | 2249 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.34 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···N2 | 0.930 | 2.600 | 2.925 (5) | 101.0 |
C5—H5A···N1 | 0.930 | 2.536 | 2.838 (5) | 99.3 |
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1,2,4-Oxadiazoles are an important class of five-membered heterocyclic compounds. Some derivatives of 1,2,4-oxadiazoles showed intrinsic analgesic (Terashita et al., 2002), antiinflammatory (Nicolaides et al., 1998) and antipicornaviral (Romero, 2001) properties. We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1, where the dashed lines indicate close C—H···N contacts which most probably are caused by the coplanar arrangement of the phenyl group and the oxadiazole system (Table 1). The other bond lengths and angles are of expected values (cf. Supplementary Material).