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In the title mol­ecule, C11H9ClN2O2, the isoxazole and benzene rings make a dihedral angle of 36.80 (2)°. Inter­molecular N—H...O and C—H...O hydrogen bonds link the mol­ecules into zigzag chains running in the [101] direction. The crystal packing exhibits weak π–π stacking inter­actions [short distances of 3.675 (2) and 3.801 (3) Å between the centroids of the benzene and isoxazole rings (at ½ − x, −y, −½ + z) and (at ½ − x, −y, ½ + z), respectively], which form stacks of mol­ecules extending along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025895/cv2248sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025895/cv2248Isup2.hkl
Contains datablock I

CCDC reference: 654859

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.082
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1630 Count of symmetry unique reflns 1019 Completeness (_total/calc) 159.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 611 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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

The derivatives of isoxazolyl carboxamides have been reported to possess various chemical and biological activities (Lee et al., 2006; Xin et al., 2005). In connection with our study of the design and synthesis of new aryl-substituted isoxazole, we prepared 3-(2-chlorophenyl)-N-methylisoxazole-5-carboxamide, (I), by a convenient method from isoxazole-5-carboxyl acid. Here, we report the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported recently for 3-(4-chlorophenyl)-N-methylisoxazole-5-carbaldehyde (Zhang et al., 2006). Atoms C11/C12/N2/O2 lies in the isoxazole ring (C7/C8/C9/N1/O1) plane, and the deviations from the least-squares plane through the ring atoms are all smaller than 0.024 (3) Å. The dihedral angle between the plane of the isoxazole and benzene (C1/C2/C3/C4/C5/C6) rings is 36.80 (2)°. The relatively short distances between the centroids of benzene (Cg1) and isoxazole (Cg2) rings from the neighbouring molecules - Cg1···Cg2i 3.675 (2) Å and Cg2···Cg1i 3.801 (3) Å indicates a presence of weak π-π interactions, which form stacks of the molecules extended along the c axis. Intermolecular N—H···O and C—H···O hydrogen bonds link the molecules into zigzag chains running in the direction [101].

Related literature top

For the crystal structure of the related compound 3-(4-chlorophenyl)-N-methylisoxazole-5-carbaldehyde, see: Zhang et al. (2006). For details of the pharmacological properties of isoxazolyl carboxamide derivatives, see: Lee et al. (2006); Xin et al. (2005).

Experimental top

A mixture of 3-(2-chlorophenyl)-isoxazole-5-carboxyl acid (8 mmol) and SOCl2 (10 ml) was heated under reflux for 7 h. The excess SOCl2 was removed on a water vacuum pump and the residue was distilled in vacuo to give carbonyl chlorides (over 85% yield). The product was dissolved in 20 ml of dry acetone, which was added to excessive 30% methylamine anhydrous solution below -5° C. After stirring vigorously at the same temperature for 1 h, the mixture was extracted with CH2Cl2 and the organic layer was washed with NaHCO3 solution, H3PO4 solution, and finally with water. The solution was dried and evaporated at 308 K (15 mm H g) to yield pale powder, which was recrystallized from ethyl acetate to obtain the product (74% yield).

Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of (I) in a hexane–dichloromethane mixture (1:1 v/v) at room temperature over a period of one week.

Refinement top

All H atoms were geometrically positioned (N—H 0.86 Å, C—H 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(parent atom).

Structure description top

The derivatives of isoxazolyl carboxamides have been reported to possess various chemical and biological activities (Lee et al., 2006; Xin et al., 2005). In connection with our study of the design and synthesis of new aryl-substituted isoxazole, we prepared 3-(2-chlorophenyl)-N-methylisoxazole-5-carboxamide, (I), by a convenient method from isoxazole-5-carboxyl acid. Here, we report the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported recently for 3-(4-chlorophenyl)-N-methylisoxazole-5-carbaldehyde (Zhang et al., 2006). Atoms C11/C12/N2/O2 lies in the isoxazole ring (C7/C8/C9/N1/O1) plane, and the deviations from the least-squares plane through the ring atoms are all smaller than 0.024 (3) Å. The dihedral angle between the plane of the isoxazole and benzene (C1/C2/C3/C4/C5/C6) rings is 36.80 (2)°. The relatively short distances between the centroids of benzene (Cg1) and isoxazole (Cg2) rings from the neighbouring molecules - Cg1···Cg2i 3.675 (2) Å and Cg2···Cg1i 3.801 (3) Å indicates a presence of weak π-π interactions, which form stacks of the molecules extended along the c axis. Intermolecular N—H···O and C—H···O hydrogen bonds link the molecules into zigzag chains running in the direction [101].

For the crystal structure of the related compound 3-(4-chlorophenyl)-N-methylisoxazole-5-carbaldehyde, see: Zhang et al. (2006). For details of the pharmacological properties of isoxazolyl carboxamide derivatives, see: Lee et al. (2006); Xin et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the c axis, showing the molecules connected by N—H···O and C—H···O hydrogen bonds (dashed lines).
3-(2-Chlorophenyl)-N-methylisoxazole-5-carboxamide top
Crystal data top
C11H9ClN2O2F(000) = 1952
Mr = 236.65Dx = 1.480 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 622 reflections
a = 18.722 (4) Åθ = 2.7–20.3°
b = 31.454 (6) ŵ = 0.34 mm1
c = 7.2137 (14) ÅT = 298 K
V = 4248.1 (14) Å3Block, colourless
Z = 160.51 × 0.40 × 0.39 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1630 independent reflections
Radiation source: fine-focus sealed tube1563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1522
Tmin = 0.844, Tmax = 0.877k = 3737
5233 measured reflectionsl = 78
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)] = 0.032H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0452P)2 + 3.3758P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
1630 reflectionsΔρmax = 0.23 e Å3
146 parametersΔρmin = 0.15 e Å3
1 restraintAbsolute structure: Flack (1983), with 737 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (7)
Crystal data top
C11H9ClN2O2V = 4248.1 (14) Å3
Mr = 236.65Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 18.722 (4) ŵ = 0.34 mm1
b = 31.454 (6) ÅT = 298 K
c = 7.2137 (14) Å0.51 × 0.40 × 0.39 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1630 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1563 reflections with I > 2σ(I)
Tmin = 0.844, Tmax = 0.877Rint = 0.024
5233 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.082Δρmax = 0.23 e Å3
S = 1.05Δρmin = 0.15 e Å3
1630 reflectionsAbsolute structure: Flack (1983), with 737 Friedel pairs
146 parametersAbsolute structure parameter: 0.05 (7)
1 restraint
Special details top

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
Cl10.40451 (3)0.01932 (2)0.63140 (14)0.0677 (3)
O10.15158 (7)0.05205 (5)0.7033 (3)0.0466 (4)
C40.28830 (11)0.02604 (7)0.7458 (3)0.0365 (5)
C100.18338 (12)0.12278 (7)0.7981 (3)0.0397 (5)
O20.12321 (9)0.13506 (6)0.7591 (3)0.0578 (5)
N20.23485 (9)0.14753 (6)0.8611 (3)0.0445 (5)
H2A0.27620.13660.88270.053*
N10.17918 (10)0.01105 (6)0.6847 (3)0.0452 (5)
C70.24522 (12)0.01304 (7)0.7449 (3)0.0349 (5)
C80.26279 (11)0.05475 (7)0.8031 (3)0.0367 (5)
H8A0.30610.06430.85060.044*
C90.20348 (11)0.07743 (7)0.7747 (3)0.0362 (5)
C50.36072 (12)0.02668 (8)0.7037 (4)0.0428 (6)
C60.39989 (14)0.06374 (9)0.7098 (4)0.0579 (8)
H6A0.44820.06330.68040.070*
C30.25671 (14)0.06454 (8)0.7907 (4)0.0462 (6)
H3A0.20810.06530.81690.055*
C20.29559 (15)0.10164 (9)0.7974 (4)0.0570 (7)
H2B0.27310.12710.82780.068*
C110.22384 (14)0.19281 (8)0.8955 (5)0.0608 (8)
H11A0.26220.20360.97020.091*
H11B0.17940.19690.95930.091*
H11C0.22270.20780.77950.091*
C10.36764 (16)0.10126 (9)0.7592 (5)0.0611 (8)
H1B0.39420.12620.76690.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0399 (3)0.0536 (4)0.1097 (6)0.0067 (3)0.0177 (4)0.0027 (4)
O10.0300 (8)0.0444 (9)0.0654 (12)0.0012 (7)0.0097 (8)0.0011 (8)
C40.0362 (11)0.0388 (12)0.0343 (13)0.0019 (9)0.0011 (9)0.0029 (10)
C100.0305 (11)0.0451 (13)0.0433 (13)0.0060 (9)0.0012 (9)0.0059 (11)
O20.0368 (9)0.0509 (10)0.0857 (14)0.0104 (8)0.0167 (9)0.0006 (10)
N20.0298 (9)0.0379 (10)0.0659 (14)0.0076 (7)0.0068 (10)0.0005 (10)
N10.0337 (10)0.0418 (11)0.0602 (14)0.0029 (8)0.0036 (9)0.0025 (10)
C70.0311 (11)0.0394 (12)0.0343 (12)0.0035 (9)0.0017 (8)0.0009 (10)
C80.0284 (11)0.0383 (12)0.0433 (13)0.0007 (9)0.0043 (9)0.0020 (10)
C90.0288 (10)0.0409 (12)0.0389 (12)0.0025 (9)0.0008 (9)0.0036 (11)
C50.0357 (11)0.0432 (13)0.0495 (15)0.0019 (10)0.0001 (10)0.0055 (11)
C60.0440 (14)0.0522 (16)0.078 (2)0.0093 (11)0.0085 (13)0.0110 (15)
C30.0475 (13)0.0405 (12)0.0507 (16)0.0059 (10)0.0026 (11)0.0019 (11)
C20.0723 (18)0.0367 (13)0.0621 (18)0.0026 (12)0.0087 (15)0.0014 (12)
C110.0513 (14)0.0430 (14)0.088 (2)0.0085 (11)0.0083 (15)0.0117 (16)
C10.0654 (17)0.0452 (15)0.073 (2)0.0159 (13)0.0044 (15)0.0035 (15)
Geometric parameters (Å, º) top
Cl1—C51.743 (3)C8—C91.336 (3)
O1—C91.359 (3)C8—H8A0.9300
O1—N11.396 (3)C5—C61.378 (3)
C4—C31.386 (3)C6—C11.373 (4)
C4—C51.390 (3)C6—H6A0.9300
C4—C71.470 (3)C3—C21.376 (4)
C10—O21.224 (3)C3—H3A0.9300
C10—N21.320 (3)C2—C11.377 (4)
C10—C91.485 (3)C2—H2B0.9300
N2—C111.460 (3)C11—H11A0.9600
N2—H2A0.8600C11—H11B0.9600
N1—C71.312 (3)C11—H11C0.9600
C7—C81.416 (3)C1—H1B0.9300
C9—O1—N1108.32 (16)C6—C5—Cl1117.47 (19)
C3—C4—C5117.0 (2)C4—C5—Cl1120.82 (17)
C3—C4—C7119.8 (2)C1—C6—C5120.1 (2)
C5—C4—C7123.1 (2)C1—C6—H6A120.0
O2—C10—N2124.4 (2)C5—C6—H6A120.0
O2—C10—C9120.7 (2)C2—C3—C4121.6 (2)
N2—C10—C9114.88 (19)C2—C3—H3A119.2
C10—N2—C11122.0 (2)C4—C3—H3A119.2
C10—N2—H2A119.0C3—C2—C1120.3 (3)
C11—N2—H2A119.0C3—C2—H2B119.9
C7—N1—O1105.85 (18)C1—C2—H2B119.9
N1—C7—C8111.17 (19)N2—C11—H11A109.5
N1—C7—C4118.6 (2)N2—C11—H11B109.5
C8—C7—C4130.2 (2)H11A—C11—H11B109.5
C9—C8—C7104.85 (19)N2—C11—H11C109.5
C9—C8—H8A127.6H11A—C11—H11C109.5
C7—C8—H8A127.6H11B—C11—H11C109.5
C8—C9—O1109.8 (2)C6—C1—C2119.4 (2)
C8—C9—C10134.9 (2)C6—C1—H1B120.3
O1—C9—C10115.23 (18)C2—C1—H1B120.3
C6—C5—C4121.7 (2)
O2—C10—N2—C111.6 (5)O2—C10—C9—C8179.7 (3)
C9—C10—N2—C11178.9 (2)N2—C10—C9—C80.2 (4)
C9—O1—N1—C70.2 (2)O2—C10—C9—O11.9 (3)
O1—N1—C7—C80.3 (3)N2—C10—C9—O1177.7 (2)
O1—N1—C7—C4178.9 (2)C3—C4—C5—C61.3 (4)
C3—C4—C7—N137.5 (3)C7—C4—C5—C6178.6 (2)
C5—C4—C7—N1142.7 (2)C3—C4—C5—Cl1175.96 (18)
C3—C4—C7—C8141.5 (2)C7—C4—C5—Cl14.2 (3)
C5—C4—C7—C838.4 (4)C4—C5—C6—C10.3 (4)
N1—C7—C8—C90.2 (3)Cl1—C5—C6—C1177.7 (2)
C4—C7—C8—C9178.8 (2)C5—C4—C3—C21.4 (4)
C7—C8—C9—O10.0 (3)C7—C4—C3—C2178.4 (2)
C7—C8—C9—C10178.0 (3)C4—C3—C2—C10.0 (4)
N1—O1—C9—C80.1 (3)C5—C6—C1—C21.8 (5)
N1—O1—C9—C10178.25 (19)C3—C2—C1—C61.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.142.983 (3)165
C8—H8A···O2i0.932.333.173 (3)151
Symmetry code: (i) x+1/4, y+1/4, z+1/4.

Experimental details

Crystal data
Chemical formulaC11H9ClN2O2
Mr236.65
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)298
a, b, c (Å)18.722 (4), 31.454 (6), 7.2137 (14)
V3)4248.1 (14)
Z16
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.51 × 0.40 × 0.39
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.844, 0.877
No. of measured, independent and
observed [I > 2σ(I)] reflections
5233, 1630, 1563
Rint0.024
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.082, 1.05
No. of reflections1630
No. of parameters146
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.15
Absolute structureFlack (1983), with 737 Friedel pairs
Absolute structure parameter0.05 (7)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.142.983 (3)164.9
C8—H8A···O2i0.932.333.173 (3)150.6
Symmetry code: (i) x+1/4, y+1/4, z+1/4.
 

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