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

Balakrishnan, B.; Praveen, C.; Seshadri, P.R.; Perumal, P.T.

doi:10.1107/S160053681300740X

organic compounds

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Volume 69| Part 4| April 2013| Page o597

doi:10.1107/S160053681300740X

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

B. Balakrishnan,^a C. Praveen,^b P. R. Seshadri ^c ^* and P. T. Perumal ^b

^aDepartment of Physics, P.T. Lee Chengalvaraya Naicker College of Engineering and Technology, Kancheepuram 631 502, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, and ^cPostgraduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 7 February 2013; accepted 18 March 2013; online 28 March 2013)

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, P n a 2₁
a = 7.909 (2) Å
b = 27.239 (8) Å
c = 5.9652 (17) Å
V = 1285.1 (6) Å³
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[F² > 2σ(F²)] = 0.038
wR(F²) = 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

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⋯Cgⁱ	0.93	2.96	3.732 (2)	141
C4—H4⋯Cgⁱⁱ	0.93	3.06	3.768 (3)	134
Symmetry codes: (i) $[-x+1, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x, -y+2, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681300740X/zj2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300740X/zj2101Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300740X/zj2101Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	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.

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

Crystal data top

C₁₆H₁₃NO₂	F(000) = 528
M_r = 251.27	D_x = 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 top

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

Refinement top

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(F_o²) + (0.052P)² + 0.0082P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2898 reflections	Δρ_max = 0.13 e Å⁻³
174 parameters	Δρ_min = −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)

Crystal data top

C₁₆H₁₃NO₂	V = 1285.1 (6) Å³
M_r = 251.27	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.909 (2) Å	µ = 0.09 mm⁻¹
b = 27.239 (8) Å	T = 295 K
c = 5.9652 (17) Å	0.35 × 0.30 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2256 reflections with I > 2σ(I)
6838 measured reflections	R_int = 0.031
2898 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
2898 reflections	Δρ_min = −0.13 e Å⁻³
174 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₂
M_r	251.27
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	7.909 (2), 27.239 (8), 5.9652 (17)
V (Å³)	1285.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6838, 2898, 2256
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.03
No. of reflections	2898
No. of parameters	174
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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	2.963	3.732 (2)	141
C4—H4···Cgⁱⁱ	0.93	3.058	3.768 (3)	134

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

Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

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Volume 69| Part 4| April 2013| Page o597

doi:10.1107/S160053681300740X

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