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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2077.
Published online 2010 July 21. doi:  10.1107/S1600536810027893
PMCID: PMC3007294

N-(4-Bromo­benzyl­idene)-3,4-dimethyl­isoxazol-5-amine

Abstract

In the title compound, C12H11BrN2O, the 4-bromo­benzaldehyde and 5-amino-3,4-dimethyl­isoxazole units are oriented at a dihedral angle of 4.89 (8)°. In the crystal, weak π–π inter­actions are present between the benzene rings at a centroid–centroid distance of 3.7862 (14) Å.

Related literature

For related structures, see: Asiri et al. (2010 [triangle]): Fun et al. (2010a [triangle],b [triangle]): Shad et al. (2008 [triangle]): Tahir et al. (2008 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-66-o2077-scheme1.jpg

Experimental

Crystal data

  • C12H11BrN2O
  • M r = 279.14
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2077-efi1.jpg
  • a = 7.6406 (4) Å
  • b = 8.8709 (5) Å
  • c = 9.1052 (5) Å
  • α = 97.024 (2)°
  • β = 102.961 (1)°
  • γ = 92.786 (2)°
  • V = 595.06 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.43 mm−1
  • T = 296 K
  • 0.30 × 0.14 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.568, T max = 0.665
  • 8212 measured reflections
  • 2119 independent reflections
  • 1643 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.059
  • S = 1.03
  • 2119 reflections
  • 147 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027893/bq2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027893/bq2226Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for the provision of research facilities.

supplementary crystallographic information

Comment

Heterocycles such as nitrogen and oxygen containing compounds are abundant in nature and are of great significance to life. We herein report the synthesis and crystal structure of title compound (I, Fig. 1).

The crystal structures of 4-chloro-2- [(E)-({4-[N-(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminio) methyl]phenolate (Shad et al., 2008), 4-bromo-2-((E)-{4-[(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl} iminiomethyl)phenolate (Tahir et al., 2008), 2-[(E)-(3,4-dimethylisoxazol-5-yl)iminomethyl]phenol (Fun et al., 2010a), 1-[(E)-(3,4-dimethylisoxazol-5-yl)iminomethyl]-2-naphthol (Fun et al., 2010b) and N-[4-(dimethylamino)benzylidene]-3,4-dimethylisoxazol-5-amine (Asiri et al., 2010) have been published previously, which contain the 5-amino-3,4-dimethylisoxazole moiety.

In (I), the 4-bromobenzaldehyde moiety A (C1—C7/BR1) and 5-amino-3,4-dimethylisoxazole moiety B (N1/C8—C12/N2/O1) are planar with r. m. s. deviations of 0.0119 Å and 0.0128 Å, respectively. The dihedral angle between A/B is 4.89 (8)°. The title compound essentially consists of monomers. Weak intramolecular H-bonding of C—H···O type (Table 1, Fig. 1) exists and complete an S(5) ring motif (Bernstein et al., 1995). There exists also π–π interaction between the centroids of phenyl rings at a distance of 3.7862 (14) Å [symmetry code: -x, 2 - y, 1 - z].

Experimental

A mixture of 4-bromobenzaldehyde (0.40 g, 0.0022 mol) and 5-amino-3,4-dimethylisoxazole (0.24 g, 0.0022 mol) in ethanol (15 ml) was refluxed for 5 h with stirring to give a light brown needles of title compound (I).

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. The dotted line indicate the intramolecular H-bond.

Crystal data

C12H11BrN2OZ = 2
Mr = 279.14F(000) = 280
Triclinic, P1Dx = 1.558 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6406 (4) ÅCell parameters from 1643 reflections
b = 8.8709 (5) Åθ = 2.3–25.3°
c = 9.1052 (5) ŵ = 3.43 mm1
α = 97.024 (2)°T = 296 K
β = 102.961 (1)°Needle, brown
γ = 92.786 (2)°0.30 × 0.14 × 0.12 mm
V = 595.06 (6) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer2119 independent reflections
Radiation source: fine-focus sealed tube1643 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.3°
ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −10→10
Tmin = 0.568, Tmax = 0.665l = −10→10
8212 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0225P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3
2119 reflections(Δ/σ)max = 0.001
147 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.17 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
Br1−0.32255 (4)1.00984 (3)0.72075 (3)0.0712 (1)
O10.4539 (2)0.51578 (18)0.30328 (18)0.0572 (6)
N10.1487 (3)0.55019 (19)0.3071 (2)0.0440 (6)
N20.5503 (3)0.4289 (3)0.2111 (3)0.0656 (8)
C10.0706 (3)0.7262 (2)0.4987 (2)0.0421 (8)
C2−0.1140 (3)0.7008 (2)0.4413 (3)0.0471 (8)
C3−0.2317 (3)0.7844 (3)0.5070 (3)0.0509 (8)
C4−0.1622 (3)0.8940 (2)0.6301 (3)0.0489 (9)
C50.0186 (4)0.9215 (3)0.6888 (3)0.0571 (9)
C60.1356 (3)0.8365 (3)0.6240 (3)0.0538 (9)
C70.1988 (3)0.6429 (2)0.4298 (3)0.0455 (8)
C80.2749 (3)0.4794 (2)0.2430 (3)0.0433 (8)
C90.2501 (3)0.3744 (2)0.1180 (3)0.0457 (8)
C100.4265 (3)0.3478 (3)0.1044 (3)0.0517 (9)
C110.4836 (4)0.2423 (3)−0.0149 (3)0.0745 (11)
C120.0764 (4)0.3028 (3)0.0200 (3)0.0659 (10)
H2−0.159150.626880.357860.0565*
H3−0.355510.766870.468870.0611*
H50.062700.996570.771390.0686*
H60.259050.853350.664570.0646*
H70.320750.658050.476910.0546*
H11A0.612690.248810.004350.1118*
H11B0.434830.27080−0.113410.1118*
H11C0.439750.13964−0.012070.1118*
H12A−0.021530.343320.058090.0989*
H12B0.072090.194620.020860.0989*
H12C0.066580.32433−0.082210.0989*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0760 (2)0.0641 (2)0.0851 (2)0.0188 (1)0.0448 (2)0.0012 (1)
O10.0487 (11)0.0650 (10)0.0542 (10)0.0090 (8)0.0134 (8)−0.0109 (8)
N10.0499 (12)0.0408 (10)0.0421 (11)0.0068 (8)0.0138 (9)0.0023 (9)
N20.0549 (14)0.0742 (14)0.0684 (15)0.0155 (11)0.0226 (12)−0.0074 (12)
C10.0501 (15)0.0399 (12)0.0394 (13)0.0059 (10)0.0163 (10)0.0061 (10)
C20.0523 (16)0.0422 (12)0.0466 (14)0.0001 (10)0.0157 (11)−0.0006 (10)
C30.0448 (15)0.0493 (13)0.0603 (16)0.0033 (10)0.0164 (12)0.0063 (12)
C40.0598 (17)0.0419 (12)0.0521 (15)0.0077 (10)0.0271 (12)0.0063 (11)
C50.0624 (19)0.0568 (15)0.0492 (15)0.0015 (12)0.0174 (12)−0.0115 (12)
C60.0456 (15)0.0632 (15)0.0486 (15)0.0020 (11)0.0104 (11)−0.0063 (12)
C70.0449 (14)0.0482 (13)0.0446 (14)0.0075 (10)0.0117 (10)0.0071 (11)
C80.0476 (15)0.0428 (12)0.0410 (13)0.0081 (10)0.0119 (10)0.0065 (10)
C90.0590 (16)0.0397 (12)0.0398 (13)0.0087 (10)0.0140 (11)0.0045 (10)
C100.0652 (17)0.0456 (13)0.0482 (15)0.0143 (12)0.0209 (13)0.0037 (11)
C110.089 (2)0.0725 (18)0.0698 (19)0.0249 (15)0.0379 (16)−0.0036 (14)
C120.073 (2)0.0616 (16)0.0553 (16)0.0060 (13)0.0070 (14)−0.0075 (13)

Geometric parameters (Å, °)

Br1—C41.899 (2)C9—C101.409 (3)
O1—N21.420 (3)C9—C121.486 (4)
O1—C81.361 (3)C10—C111.500 (4)
N1—C71.274 (3)C2—H20.9300
N1—C81.374 (3)C3—H30.9300
N2—C101.307 (4)C5—H50.9300
C1—C21.387 (3)C6—H60.9300
C1—C61.390 (3)C7—H70.9300
C1—C71.460 (3)C11—H11A0.9600
C2—C31.384 (3)C11—H11B0.9600
C3—C41.378 (4)C11—H11C0.9600
C4—C51.363 (4)C12—H12A0.9600
C5—C61.382 (4)C12—H12B0.9600
C8—C91.351 (3)C12—H12C0.9600
Br1···C11i3.595 (3)C4···C6ii3.553 (3)
Br1···C7ii3.687 (2)C6···C4ii3.553 (3)
O1···C3iii3.355 (3)C7···Br1ii3.687 (2)
O1···H3iii2.6900C7···C2iv3.481 (3)
O1···H72.3400C8···C3iv3.512 (3)
N1···C2iv3.426 (3)C11···Br1viii3.595 (3)
N1···H22.6000H2···N12.6000
N1···H12A2.7600H2···N2vii2.7400
N1···H12Cv2.7100H3···O1vii2.6900
N2···H2iii2.7400H6···H72.4200
N2···H11Bvi2.9100H7···O12.3400
C2···N1iv3.426 (3)H7···H62.4200
C2···C7iv3.481 (3)H11B···N2vi2.9100
C3···O1vii3.355 (3)H12A···N12.7600
C3···C8iv3.512 (3)H12C···N1v2.7100
N2—O1—C8107.76 (18)C1—C2—H2120.00
C7—N1—C8119.9 (2)C3—C2—H2120.00
O1—N2—C10105.0 (2)C2—C3—H3121.00
C2—C1—C6118.9 (2)C4—C3—H3121.00
C2—C1—C7122.08 (18)C4—C5—H5120.00
C6—C1—C7119.0 (2)C6—C5—H5120.00
C1—C2—C3120.6 (2)C1—C6—H6120.00
C2—C3—C4118.8 (2)C5—C6—H6120.00
Br1—C4—C3119.17 (18)N1—C7—H7119.00
Br1—C4—C5119.02 (19)C1—C7—H7119.00
C3—C4—C5121.8 (2)C10—C11—H11A109.00
C4—C5—C6119.2 (2)C10—C11—H11B109.00
C1—C6—C5120.6 (2)C10—C11—H11C109.00
N1—C7—C1122.0 (2)H11A—C11—H11B109.00
O1—C8—N1120.5 (2)H11A—C11—H11C109.00
O1—C8—C9110.4 (2)H11B—C11—H11C109.00
N1—C8—C9129.2 (2)C9—C12—H12A109.00
C8—C9—C10103.9 (2)C9—C12—H12B109.00
C8—C9—C12127.6 (2)C9—C12—H12C109.00
C10—C9—C12128.5 (2)H12A—C12—H12B110.00
N2—C10—C9113.0 (2)H12A—C12—H12C109.00
N2—C10—C11118.9 (2)H12B—C12—H12C109.00
C9—C10—C11128.1 (2)
C8—O1—N2—C10−0.1 (3)C1—C2—C3—C40.3 (4)
N2—O1—C8—C90.1 (2)C2—C3—C4—Br1179.81 (18)
N2—O1—C8—N1−178.1 (2)C2—C3—C4—C5−0.3 (4)
C7—N1—C8—C9177.3 (2)Br1—C4—C5—C6179.42 (19)
C8—N1—C7—C1177.18 (18)C3—C4—C5—C6−0.5 (4)
C7—N1—C8—O1−4.8 (3)C4—C5—C6—C11.2 (4)
O1—N2—C10—C90.1 (3)O1—C8—C9—C100.0 (3)
O1—N2—C10—C11179.6 (2)N1—C8—C9—C12−2.8 (4)
C2—C1—C6—C5−1.2 (3)O1—C8—C9—C12179.1 (2)
C6—C1—C2—C30.4 (3)N1—C8—C9—C10178.0 (2)
C7—C1—C2—C3−178.4 (2)C8—C9—C10—N2−0.1 (3)
C7—C1—C6—C5177.6 (2)C12—C9—C10—C111.4 (4)
C2—C1—C7—N15.0 (3)C8—C9—C10—C11−179.5 (3)
C6—C1—C7—N1−173.7 (2)C12—C9—C10—N2−179.2 (2)

Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+2, −z+1; (iii) x+1, y, z; (iv) −x, −y+1, −z+1; (v) −x, −y+1, −z; (vi) −x+1, −y+1, −z; (vii) x−1, y, z; (viii) x+1, y−1, z−1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O10.93002.34002.702 (3)103.00

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2226).

References

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  • Fun, H.-K., Hemamalini, M., Asiri, A. M., Khan, S. A. & Khan, K. A. (2010b). Acta Cryst. E66, o773–o774. [PMC free article] [PubMed]
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