5-(3-Meth­oxy­phen­yl)-3-phenyl-1,2-oxazole

Abstract

In the title compound, C₁₆H₁₃NO₂, the isoxazole ring makes dihedral angles of 17.1 (1)° with the 3-meth­oxy­phenyl ring and 15.2 (1)° with the phenyl group. Centrosymmetric dimers that are realised by pairs of C—H⋯π inter­actions are observed in the crystal structure.

Related literature  

For general background to isoxazole derivaties, see: Sperry & Wright (2005 ▶); Tanaka et al. (2007 ▶). For their biological activity, see: Stevens & Albizati (1984 ▶). For related structures, see: Samshuddin et al. (2011 ▶); Balakrishnan et al. (2011 ▶).

Experimental  

Crystal data  

• C₁₆H₁₃NO₂

• M _r = 251.27

• Orthorhombic,

• a = 7.909 (2) Å

• b = 27.239 (8) Å

• c = 5.9652 (17) Å

• V = 1285.1 (6) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 295 K

• 0.35 × 0.30 × 0.30 mm

Data collection  

• Bruker Kappa APEXII CCD diffractometer

• 6838 measured reflections

• 2898 independent reflections

• 2256 reflections with I > 2σ(I)

• R _int = 0.031

Refinement  

• R[F ² > 2σ(F ²)] = 0.038

• wR(F ²) = 0.103

• S = 1.03

• 2898 reflections

• 174 parameters

• 2 restraints

• H-atom parameters constrained

• Δρ_max = 0.13 e Å⁻³

• Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg i	0.93	2.96	3.732 (2)	141
C4—H4⋯Cg ii	0.93	3.06	3.768 (3)	134

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

Isoxazoles are important class of heteroaromatic molecules which are components in a variety of natural products and medicinally useful compounds (Sperry & Wright, 2005). Isoxazole also finds application in organic synthesis as synthetic intermediates and chiral ligands. The liquid crystalline property of isoxazole derivatives and its potential application in optoelectric devices made them attractive synthetic target (Tanaka et al., 2007)

Isoxazole derivaties bearing different substituents are known to have various biological activities in pharmaceutical and agricultural areas. Isoxazole compounds have been widely studied because they exhibit some fungicidal activity, plant -growth regulating activity and antibacterial activity (Stevens & Albizati, 1984). In the title compound the isoxazole ring makes a dihedral angle of 17.1 (1)° with methoxy phenyl ring C10/C11/C12/C13/C14/C15/O2/C16 and a dihedral angle of 15.2 (1)° with the phenyl ring C1/C2/C3/C4/C5/C6 attached to the planar isoxazole moiety.The geometrical parameters agree well with the reported structure (Samshuddin et al.2011; Balakrishnan et al. 2011). A Centrosymmetric dimers are formed by C—H···π (C1—H1···Cg and C5—H5···Cg) interactions, where Cg is the centroid of the ring C1—C6 (Fig. 2).

Experimental

To solution of 1-phenyl-3-m-tolyl-propynone oxime (251 mg, 1.0 (mmol) in dry dichloromethane (1 ml) was added AuCl₃ (3.03 mg, 1 mol%) under N₂ atmosphere and stirred for 10 min. After completion of the reaction as indicated by TLC, the reaction mixture was concentrated under reduced pressure and purified by colomn chromatography over silica gel (100–200 mech) using EtOAc/hexane to afford the pure product.

Refinement

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H=0.93–0.97 Å and U_iso (H)= 1.5Ueq(C) for methyl H atoms and 1.2 U_eq(C) for other H atoms.

Figures

Fig. 1.

Molecular structure of the title compound, showing 30% probability displacement ellipsoids.

Fig. 2.

A view of the C—H···π interactions in the crystal structure of the title compound.

Crystal data

C16H13NO2	F(000) = 528
Mr = 251.27	Dx = 1.299 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2593 reflections
a = 7.909 (2) Å	θ = 2.7–28.4°
b = 27.239 (8) Å	µ = 0.09 mm−1
c = 5.9652 (17) Å	T = 295 K
V = 1285.1 (6) Å3	Block, colourless
Z = 4	0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	2256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.4°, θmin = 2.7°
ω and φ scan	h = −10→8
6838 measured reflections	k = −36→32
2898 independent reflections	l = −7→6

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.052P)2 + 0.0082P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2898 reflections	Δρmax = 0.13 e Å−3
174 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (19)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6539 (2)	0.00884 (6)	0.6796 (4)	0.0597 (5)
H1	0.5895	0.0187	0.8020	0.072*
C2	0.7022 (3)	−0.03964 (7)	0.6594 (4)	0.0713 (6)
H2	0.6680	−0.0624	0.7665	0.086*
C3	0.8006 (3)	−0.05449 (7)	0.4817 (4)	0.0735 (6)
H3	0.8334	−0.0872	0.4693	0.088*
C4	0.8501 (3)	−0.02114 (8)	0.3231 (5)	0.0739 (6)
H4	0.9178	−0.0311	0.2041	0.089*
C5	0.7994 (2)	0.02776 (7)	0.3393 (4)	0.0640 (5)
H5	0.8317	0.0502	0.2299	0.077*
C6	0.70095 (19)	0.04300 (6)	0.5184 (3)	0.0494 (4)
C7	0.6472 (2)	0.09484 (6)	0.5388 (3)	0.0485 (4)
C8	0.5818 (2)	0.11998 (6)	0.7237 (3)	0.0493 (4)
H8	0.5592	0.1074	0.8655	0.059*
C9	0.5583 (2)	0.16697 (6)	0.6515 (3)	0.0471 (4)
C10	0.49808 (19)	0.21163 (6)	0.7641 (3)	0.0476 (4)
C11	0.4136 (2)	0.20828 (7)	0.9665 (3)	0.0584 (4)
H11	0.3926	0.1777	1.0304	0.070*
C12	0.3606 (2)	0.25068 (8)	1.0733 (3)	0.0637 (5)
H12	0.3037	0.2485	1.2093	0.076*
C13	0.3916 (2)	0.29611 (7)	0.9793 (3)	0.0619 (5)
H13	0.3544	0.3244	1.0514	0.074*
C14	0.4776 (2)	0.29962 (6)	0.7785 (3)	0.0520 (4)
C15	0.5295 (2)	0.25759 (6)	0.6679 (3)	0.0503 (4)
H15	0.5848	0.2599	0.5307	0.060*
C16	0.5937 (3)	0.35244 (7)	0.4984 (4)	0.0720 (6)
H16A	0.5336	0.3357	0.3813	0.108*
H16B	0.7054	0.3390	0.5115	0.108*
H16C	0.6011	0.3868	0.4631	0.108*
N	0.6620 (2)	0.12403 (5)	0.3651 (3)	0.0628 (4)
O1	0.60346 (19)	0.17058 (5)	0.4372 (2)	0.0689 (4)
O2	0.50660 (17)	0.34640 (5)	0.7034 (2)	0.0704 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0586 (10)	0.0583 (10)	0.0624 (12)	0.0025 (8)	0.0068 (10)	0.0017 (9)
C2	0.0738 (12)	0.0572 (11)	0.0830 (16)	0.0021 (9)	0.0046 (12)	0.0100 (10)
C3	0.0691 (12)	0.0575 (11)	0.0939 (18)	0.0050 (9)	−0.0027 (13)	−0.0120 (11)
C4	0.0713 (12)	0.0695 (12)	0.0807 (16)	−0.0010 (10)	0.0139 (12)	−0.0203 (11)
C5	0.0665 (11)	0.0624 (11)	0.0629 (12)	−0.0055 (9)	0.0102 (10)	−0.0061 (10)
C6	0.0423 (8)	0.0512 (8)	0.0546 (10)	−0.0051 (7)	−0.0020 (8)	−0.0051 (8)
C7	0.0439 (8)	0.0510 (8)	0.0507 (9)	−0.0073 (7)	0.0006 (8)	−0.0013 (8)
C8	0.0507 (8)	0.0514 (8)	0.0457 (10)	−0.0020 (7)	0.0026 (7)	0.0047 (7)
C9	0.0464 (8)	0.0517 (9)	0.0432 (10)	−0.0046 (7)	−0.0041 (8)	0.0013 (7)
C10	0.0423 (8)	0.0544 (9)	0.0462 (10)	0.0012 (7)	−0.0057 (7)	−0.0015 (7)
C11	0.0543 (10)	0.0713 (11)	0.0494 (10)	0.0017 (8)	−0.0034 (9)	0.0027 (9)
C12	0.0578 (11)	0.0870 (14)	0.0462 (11)	0.0111 (9)	0.0013 (9)	−0.0042 (9)
C13	0.0558 (10)	0.0756 (12)	0.0544 (12)	0.0154 (8)	−0.0081 (9)	−0.0164 (9)
C14	0.0462 (9)	0.0547 (10)	0.0551 (11)	0.0043 (7)	−0.0095 (8)	−0.0082 (8)
C15	0.0448 (9)	0.0556 (10)	0.0504 (10)	0.0016 (7)	−0.0024 (8)	−0.0039 (8)
C16	0.0820 (14)	0.0548 (10)	0.0791 (16)	−0.0039 (9)	−0.0051 (12)	0.0030 (10)
N	0.0935 (12)	0.0494 (7)	0.0455 (9)	0.0024 (7)	0.0110 (8)	−0.0002 (6)
O1	0.1073 (10)	0.0510 (6)	0.0485 (8)	0.0060 (7)	0.0055 (7)	0.0026 (5)
O2	0.0790 (9)	0.0518 (7)	0.0805 (10)	0.0030 (6)	0.0026 (8)	−0.0072 (7)

Geometric parameters (Å, º)

C1—C2	1.380 (3)	C9—C10	1.469 (2)
C1—C6	1.389 (3)	C10—C11	1.383 (2)
C1—H1	0.9300	C10—C15	1.400 (2)
C2—C3	1.376 (3)	C11—C12	1.384 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.369 (3)	C12—C13	1.380 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.394 (3)	C13—C14	1.381 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.385 (3)	C14—O2	1.370 (2)
C5—H5	0.9300	C14—C15	1.384 (2)
C6—C7	1.480 (2)	C15—H15	0.9300
C7—N	1.311 (2)	C16—O2	1.413 (3)
C7—C8	1.398 (2)	C16—H16A	0.9600
C8—C9	1.363 (2)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C9—O1	1.331 (2)	N—O1	1.4165 (19)
C2—C1—C6	120.42 (19)	C11—C10—C15	120.20 (16)
C2—C1—H1	119.8	C11—C10—C9	120.10 (15)
C6—C1—H1	119.8	C15—C10—C9	119.70 (16)
C3—C2—C1	120.3 (2)	C10—C11—C12	119.55 (18)
C3—C2—H2	119.8	C10—C11—H11	120.2
C1—C2—H2	119.8	C12—C11—H11	120.2
C4—C3—C2	119.96 (19)	C13—C12—C11	120.50 (19)
C4—C3—H3	120.0	C13—C12—H12	119.7
C2—C3—H3	120.0	C11—C12—H12	119.7
C3—C4—C5	120.2 (2)	C12—C13—C14	120.10 (17)
C3—C4—H4	119.9	C12—C13—H13	119.9
C5—C4—H4	119.9	C14—C13—H13	119.9
C6—C5—C4	120.08 (19)	O2—C14—C13	115.50 (16)
C6—C5—H5	120.0	O2—C14—C15	124.32 (17)
C4—C5—H5	120.0	C13—C14—C15	120.18 (17)
C5—C6—C1	118.94 (16)	C14—C15—C10	119.45 (17)
C5—C6—C7	120.71 (16)	C14—C15—H15	120.3
C1—C6—C7	120.35 (17)	C10—C15—H15	120.3
N—C7—C8	111.07 (14)	O2—C16—H16A	109.5
N—C7—C6	119.20 (16)	O2—C16—H16B	109.5
C8—C7—C6	129.71 (16)	H16A—C16—H16B	109.5
C9—C8—C7	105.12 (15)	O2—C16—H16C	109.5
C9—C8—H8	127.4	H16A—C16—H16C	109.5
C7—C8—H8	127.4	H16B—C16—H16C	109.5
O1—C9—C8	109.67 (16)	C7—N—O1	105.89 (14)
O1—C9—C10	117.72 (15)	C9—O1—N	108.24 (14)
C8—C9—C10	132.60 (16)	C14—O2—C16	118.23 (14)
C6—C1—C2—C3	1.4 (3)	C8—C9—C10—C15	162.56 (17)
C1—C2—C3—C4	−0.4 (3)	C15—C10—C11—C12	−0.1 (2)
C2—C3—C4—C5	−0.8 (3)	C9—C10—C11—C12	178.65 (16)
C3—C4—C5—C6	1.1 (3)	C10—C11—C12—C13	0.0 (3)
C4—C5—C6—C1	−0.1 (3)	C11—C12—C13—C14	−0.7 (3)
C4—C5—C6—C7	179.55 (18)	C12—C13—C14—O2	−177.92 (15)
C2—C1—C6—C5	−1.1 (3)	C12—C13—C14—C15	1.6 (2)
C2—C1—C6—C7	179.22 (17)	O2—C14—C15—C10	177.77 (14)
C5—C6—C7—N	14.4 (2)	C13—C14—C15—C10	−1.7 (2)
C1—C6—C7—N	−165.93 (17)	C11—C10—C15—C14	0.9 (2)
C5—C6—C7—C8	−164.38 (18)	C9—C10—C15—C14	−177.80 (14)
C1—C6—C7—C8	15.3 (3)	C8—C7—N—O1	−0.2 (2)
N—C7—C8—C9	−0.4 (2)	C6—C7—N—O1	−179.16 (14)
C6—C7—C8—C9	178.48 (16)	C8—C9—O1—N	−0.93 (19)
C7—C8—C9—O1	0.81 (18)	C10—C9—O1—N	178.15 (13)
C7—C8—C9—C10	−178.09 (17)	C7—N—O1—C9	0.7 (2)
O1—C9—C10—C11	165.00 (15)	C13—C14—O2—C16	−179.83 (16)
C8—C9—C10—C11	−16.2 (3)	C15—C14—O2—C16	0.7 (2)
O1—C9—C10—C15	−16.3 (2)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cgi	0.93	2.96	3.732 (2)	141
C4—H4···Cgii	0.93	3.06	3.768 (3)	134

Symmetry codes: (i) −x+1, −y+2, z−1/2; (ii) −x, −y+2, z+1/2.