Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056073/kj2072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056073/kj2072Isup2.hkl |
CCDC reference: 674081
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
For related literature, see: Juraszyk et al. (1997); Naka & Kubo (1999); Nicolaides et al. (1998); Romero (2001); Terashita et al. (2002).
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.
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.
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 the title compound, showing displacement ellipsoids at the 30% probability level. |
C10H9ClN2O | F(000) = 864 |
Mr = 208.64 | Dx = 1.387 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 25.462 (5) Å | θ = 9–13° |
b = 6.4040 (13) Å | µ = 0.35 mm−1 |
c = 14.589 (3) Å | T = 293 K |
β = 122.83 (3)° | Block, colourless |
V = 1998.9 (7) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 8 |
Enraf–Nonius CAD-4 diffractometer | 1259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ω/2θ scans | h = −31→26 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.873, Tmax = 0.966 | l = 0→17 |
2002 measured reflections | 3 standard reflections every 200 reflections |
1959 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C10H9ClN2O | V = 1998.9 (7) Å3 |
Mr = 208.64 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.462 (5) Å | µ = 0.35 mm−1 |
b = 6.4040 (13) Å | T = 293 K |
c = 14.589 (3) Å | 0.40 × 0.10 × 0.10 mm |
β = 122.83 (3)° |
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 = 0.966 | 3 standard reflections every 200 reflections |
2002 measured reflections | intensity decay: none |
1959 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.28 e Å−3 |
1959 reflections | Δρmin = −0.31 e Å−3 |
127 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl | 0.02222 (5) | 0.14389 (18) | 0.38492 (8) | 0.0812 (4) | |
O | 0.08264 (11) | 0.5594 (4) | 0.5539 (2) | 0.0601 (7) | |
N1 | 0.13240 (13) | 0.7029 (4) | 0.5847 (3) | 0.0609 (8) | |
N2 | 0.16296 (12) | 0.3737 (4) | 0.5827 (2) | 0.0468 (7) | |
C1 | 0.41839 (18) | 0.8720 (6) | 0.7058 (3) | 0.0729 (11) | |
H1B | 0.4470 | 0.7565 | 0.7324 | 0.109* | |
H1C | 0.4341 | 0.9795 | 0.7603 | 0.109* | |
H1D | 0.4141 | 0.9262 | 0.6407 | 0.109* | |
C2 | 0.35583 (15) | 0.7997 (6) | 0.6807 (3) | 0.0523 (8) | |
C3 | 0.34571 (16) | 0.5951 (5) | 0.6953 (3) | 0.0562 (9) | |
H3A | 0.3785 | 0.5003 | 0.7223 | 0.067* | |
C4 | 0.28841 (15) | 0.5270 (5) | 0.6712 (3) | 0.0532 (8) | |
H4A | 0.2830 | 0.3877 | 0.6823 | 0.064* | |
C5 | 0.23873 (15) | 0.6639 (5) | 0.6305 (2) | 0.0449 (7) | |
C6 | 0.24793 (17) | 0.8724 (5) | 0.6149 (3) | 0.0528 (8) | |
H6A | 0.2152 | 0.9675 | 0.5877 | 0.063* | |
C7 | 0.30605 (18) | 0.9360 (5) | 0.6403 (3) | 0.0572 (9) | |
H7A | 0.3119 | 1.0752 | 0.6299 | 0.069* | |
C8 | 0.17730 (14) | 0.5851 (5) | 0.5989 (2) | 0.0445 (7) | |
C9 | 0.10588 (16) | 0.3704 (5) | 0.5555 (2) | 0.0470 (8) | |
C10 | 0.06392 (17) | 0.1880 (5) | 0.5267 (3) | 0.0561 (9) | |
H10A | 0.0348 | 0.2134 | 0.5489 | 0.067* | |
H10B | 0.0884 | 0.0652 | 0.5650 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0833 (8) | 0.0822 (8) | 0.0651 (6) | −0.0317 (6) | 0.0317 (5) | −0.0112 (5) |
O | 0.0480 (13) | 0.0442 (13) | 0.0893 (18) | 0.0034 (11) | 0.0381 (13) | −0.0040 (12) |
N1 | 0.0509 (17) | 0.0406 (15) | 0.090 (2) | −0.0009 (13) | 0.0376 (16) | −0.0041 (14) |
N2 | 0.0492 (16) | 0.0377 (14) | 0.0543 (15) | −0.0016 (12) | 0.0286 (13) | −0.0022 (11) |
C1 | 0.061 (2) | 0.083 (3) | 0.077 (3) | −0.018 (2) | 0.039 (2) | −0.009 (2) |
C2 | 0.052 (2) | 0.056 (2) | 0.0490 (18) | −0.0086 (16) | 0.0272 (16) | −0.0069 (15) |
C3 | 0.0445 (18) | 0.057 (2) | 0.060 (2) | 0.0084 (16) | 0.0232 (16) | 0.0049 (16) |
C4 | 0.0466 (19) | 0.0419 (18) | 0.064 (2) | 0.0008 (15) | 0.0258 (16) | 0.0029 (15) |
C5 | 0.0508 (18) | 0.0376 (16) | 0.0449 (16) | 0.0003 (14) | 0.0250 (14) | 0.0000 (13) |
C6 | 0.059 (2) | 0.0407 (18) | 0.060 (2) | 0.0054 (15) | 0.0329 (17) | −0.0006 (15) |
C7 | 0.069 (2) | 0.0417 (18) | 0.071 (2) | −0.0102 (17) | 0.0441 (19) | −0.0065 (16) |
C8 | 0.0460 (18) | 0.0393 (17) | 0.0467 (17) | 0.0028 (14) | 0.0241 (14) | 0.0009 (12) |
C9 | 0.0516 (19) | 0.0436 (18) | 0.0482 (17) | 0.0025 (14) | 0.0287 (15) | −0.0019 (14) |
C10 | 0.056 (2) | 0.0485 (19) | 0.068 (2) | −0.0053 (16) | 0.0358 (17) | 0.0027 (16) |
Cl—C10 | 1.761 (4) | C3—C4 | 1.373 (5) |
O—C9 | 1.342 (4) | C3—H3A | 0.9300 |
O—N1 | 1.426 (4) | C4—C5 | 1.381 (4) |
N1—C8 | 1.289 (4) | C4—H4A | 0.9300 |
N2—C9 | 1.282 (4) | C5—C6 | 1.395 (4) |
N2—C8 | 1.389 (4) | C5—C8 | 1.460 (5) |
C1—C2 | 1.501 (5) | C6—C7 | 1.378 (5) |
C1—H1B | 0.9600 | C6—H6A | 0.9300 |
C1—H1C | 0.9600 | C7—H7A | 0.9300 |
C1—H1D | 0.9600 | C9—C10 | 1.482 (4) |
C2—C3 | 1.374 (5) | C10—H10A | 0.9700 |
C2—C7 | 1.380 (5) | C10—H10B | 0.9700 |
C9—O—N1 | 105.5 (2) | C6—C5—C8 | 121.7 (3) |
C8—N1—O | 103.5 (3) | C7—C6—C5 | 119.3 (3) |
C9—N2—C8 | 102.6 (3) | C7—C6—H6A | 120.3 |
C2—C1—H1B | 109.5 | C5—C6—H6A | 120.3 |
C2—C1—H1C | 109.5 | C6—C7—C2 | 122.1 (3) |
H1B—C1—H1C | 109.5 | C6—C7—H7A | 118.9 |
C2—C1—H1D | 109.5 | C2—C7—H7A | 118.9 |
H1B—C1—H1D | 109.5 | N1—C8—N2 | 114.5 (3) |
H1C—C1—H1D | 109.5 | N1—C8—C5 | 123.6 (3) |
C3—C2—C7 | 117.6 (3) | N2—C8—C5 | 121.9 (3) |
C3—C2—C1 | 121.3 (3) | N2—C9—O | 113.9 (3) |
C7—C2—C1 | 121.1 (3) | N2—C9—C10 | 128.5 (3) |
C4—C3—C2 | 121.7 (3) | O—C9—C10 | 117.6 (3) |
C4—C3—H3A | 119.1 | C9—C10—Cl | 110.0 (2) |
C2—C3—H3A | 119.1 | C9—C10—H10A | 109.7 |
C3—C4—C5 | 120.4 (3) | Cl—C10—H10A | 109.7 |
C3—C4—H4A | 119.8 | C9—C10—H10B | 109.7 |
C5—C4—H4A | 119.8 | Cl—C10—H10B | 109.7 |
C4—C5—C6 | 118.8 (3) | H10A—C10—H10B | 108.2 |
C4—C5—C8 | 119.4 (3) | ||
C9—O—N1—C8 | 0.8 (3) | C9—N2—C8—N1 | 1.2 (4) |
C7—C2—C3—C4 | −0.1 (5) | C9—N2—C8—C5 | −179.3 (3) |
C1—C2—C3—C4 | −179.1 (3) | C4—C5—C8—N1 | 163.2 (3) |
C2—C3—C4—C5 | 0.3 (5) | C6—C5—C8—N1 | −20.5 (5) |
C3—C4—C5—C6 | −0.3 (5) | C4—C5—C8—N2 | −16.2 (5) |
C3—C4—C5—C8 | 176.1 (3) | C6—C5—C8—N2 | 160.1 (3) |
C4—C5—C6—C7 | 0.1 (5) | C8—N2—C9—O | −0.7 (4) |
C8—C5—C6—C7 | −176.3 (3) | C8—N2—C9—C10 | 179.5 (3) |
C5—C6—C7—C2 | 0.1 (5) | N1—O—C9—N2 | −0.1 (4) |
C3—C2—C7—C6 | −0.1 (5) | N1—O—C9—C10 | 179.8 (3) |
C1—C2—C7—C6 | 178.9 (3) | N2—C9—C10—Cl | −91.1 (4) |
O—N1—C8—N2 | −1.3 (4) | O—C9—C10—Cl | 89.1 (3) |
O—N1—C8—C5 | 179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···N2 | 0.93 | 2.58 | 2.892 (5) | 100 |
C10—H10B···N1i | 0.97 | 2.52 | 3.436 (5) | 157 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H9ClN2O |
Mr | 208.64 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 25.462 (5), 6.4040 (13), 14.589 (3) |
β (°) | 122.83 (3) |
V (Å3) | 1998.9 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.873, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2002, 1959, 1259 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.182, 1.02 |
No. of reflections | 1959 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···N1i | 0.9700 | 2.5200 | 3.436 (5) | 157.00 |
Symmetry code: (i) x, y−1, z. |
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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.