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

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

doi:10.1107/S1600536811020198

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1575

doi:10.1107/S1600536811020198

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5-(3-Methylphenyl)-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 & Technology, Kancheepuram 631 502, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, and ^cPostGraduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 10 April 2011; accepted 26 May 2011; online 4 June 2011)

In the title compound, C₁₆H₁₃NO, the isoxazole ring makes dihedral angles of 16.64 (7)° with 3-methylphenzyl ring and 17.60 (7)° with the unsubstituted phenyl ring.

Related literature

For general background to isoxazole derivatives, see: Sperry & Wright (2005 ); Krogsgaard-Larsen et al. (1996 ); Deng et al. (2009 ); Talley (1999 ).

Experimental

Crystal data

C₁₆H₁₃NO
M_r = 235.27
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8052 (2) Å
b = 7.7010 (3) Å
c = 27.4363 (8) Å
V = 1226.56 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.977, T_max = 0.984
14583 measured reflections
1599 independent reflections
1302 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.08
1599 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020198/bt5513sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020198/bt5513Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020198/bt5513Isup3.cml

checkCIF report

Comment top

Isoxazoles are an important class of heteroaromatic molecules which are components in a variety of natural products and medicinally useful compounds (Sperry et al., 2005). For example, the natural product ibotenic acid, an active constituent of the psychotrophic fly agaric mushroom amanita muscaria, acts at both ionotropic and metabotropic glutamate receptor subtypes (Krogsgaard-Larsen et al., 1996). Isoxazole systems have also been targeted in synthetic investigations for their known bological and pharmacological properties such as hypoglycemic, anti-inflammatory and anti-bacterial activities. The growing interest in such analogues also rises from their high potential value as antiviral agents (Deng et al., 2009). Valdecoxib is a nonsteroidal anti-inflammatory drug used in the treatment of osteoarthritis, rheumatoid arthritis and powerful menstration and menstrual symptoms (Talley, 1999). In the title compound the isoxazole ring makes a dihedral angle of 16.64 (7)° with methyl benzyl ring (C10/C11/C12/C13/C14/C15/C16) and a dihedral angle of 17.60 (7)° with the phenyl ring (C1/C2/C3/C4/C5/C6) attached to the planar isoxazole moiety.

Related literature top

For general background to isoxazole derivatives, see: Sperry & Wright (2005); Krogsgaard-Larsen et al. (1996); Deng et al. (2009); Talley (1999).

Experimental top

To a solution of 1-phenyl-3-m-tolyl-propynone oxime (235 mg, 1.0(mmol) in dry dichloromethane (1 ml) wasadded AuCl3 (3.03 mg, 1mol%) under N2 atmosphere and stirred for 10 min. After completion of the reaction as indicated by TLC the reaction mixture was concertrated under reduced pressure and purified by column chromatography over silica gel(100–200mech) Et 0 Ac/hexane to afford the pure product.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.

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

Crystal data top

C₁₆H₁₃NO	D_x = 1.274 Mg m⁻³
M_r = 235.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 14583 reflections
a = 5.8052 (2) Å	θ = 1.5–27.1°
b = 7.7010 (3) Å	µ = 0.08 mm⁻¹
c = 27.4363 (8) Å	T = 293 K
V = 1226.56 (7) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 496

Data collection top

Bruker Kappa APEXII area-detector diffractometer	1599 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
T_min = 0.977, T_max = 0.984	k = −8→9
14583 measured reflections	l = −35→35

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0547P)² + 0.1446P] where P = (F_o² + 2F_c²)/3
1599 reflections	(Δ/σ)_max = 0.003
164 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₃NO	V = 1226.56 (7) Å³
M_r = 235.27	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8052 (2) Å	µ = 0.08 mm⁻¹
b = 7.7010 (3) Å	T = 293 K
c = 27.4363 (8) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	1599 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1302 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.034
14583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	Δρ_max = 0.12 e Å⁻³
1599 reflections	Δρ_min = −0.18 e Å⁻³
164 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
N	0.3214 (3)	0.4492 (3)	0.09265 (7)	0.0550 (5)
O	0.3690 (3)	0.3988 (3)	0.14108 (6)	0.0662 (5)
C9	0.5947 (4)	0.3630 (3)	0.14404 (8)	0.0492 (6)
C10	0.6819 (4)	0.3105 (3)	0.19162 (8)	0.0471 (5)
C14	0.6336 (4)	0.2897 (3)	0.27920 (8)	0.0498 (5)
C7	0.5182 (4)	0.4406 (3)	0.06915 (8)	0.0505 (5)
C15	0.5545 (4)	0.3395 (3)	0.23393 (8)	0.0491 (5)
H15	0.4121	0.3941	0.2315	0.059*
C13	0.8460 (4)	0.2078 (3)	0.28208 (9)	0.0553 (6)
H13	0.9016	0.1721	0.3123	0.066*
C8	0.6941 (4)	0.3875 (3)	0.09969 (8)	0.0526 (6)
H8	0.8483	0.3718	0.0916	0.063*
C1	0.7032 (5)	0.4368 (3)	−0.01203 (9)	0.0650 (7)
H1	0.8257	0.3757	0.0015	0.078*
C12	0.9760 (5)	0.1786 (3)	0.24080 (10)	0.0603 (6)
H12	1.1181	0.1237	0.2434	0.072*
C11	0.8968 (4)	0.2303 (3)	0.19575 (10)	0.0556 (6)
H11	0.9863	0.2119	0.1681	0.067*
C6	0.5200 (4)	0.4874 (3)	0.01707 (8)	0.0506 (5)
C5	0.3401 (5)	0.5778 (3)	−0.00369 (9)	0.0627 (7)
H5	0.2162	0.6123	0.0155	0.075*
C16	0.4918 (5)	0.3241 (4)	0.32435 (9)	0.0708 (8)
H16A	0.4844	0.4469	0.3302	0.106*
H16B	0.5620	0.2679	0.3518	0.106*
H16C	0.3390	0.2795	0.3198	0.106*
C4	0.3426 (5)	0.6172 (4)	−0.05246 (10)	0.0718 (8)
H4	0.2208	0.6784	−0.0662	0.086*
C3	0.5239 (5)	0.5667 (4)	−0.08088 (10)	0.0739 (8)
H3	0.5248	0.5934	−0.1139	0.089*
C2	0.7041 (6)	0.4771 (4)	−0.06096 (10)	0.0728 (8)
H2	0.8272	0.4432	−0.0804	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0399 (10)	0.0734 (13)	0.0517 (11)	0.0032 (11)	0.0004 (9)	0.0030 (10)
O	0.0460 (9)	0.0866 (13)	0.0659 (11)	0.0012 (10)	0.0061 (9)	0.0003 (10)
C9	0.0397 (11)	0.0458 (12)	0.0622 (14)	−0.0024 (10)	0.0069 (10)	−0.0042 (11)
C10	0.0386 (10)	0.0410 (10)	0.0618 (13)	−0.0057 (10)	0.0035 (11)	−0.0007 (10)
C14	0.0464 (12)	0.0423 (11)	0.0607 (13)	−0.0042 (10)	0.0005 (11)	0.0011 (10)
C7	0.0461 (12)	0.0453 (11)	0.0599 (13)	−0.0042 (11)	0.0024 (11)	−0.0036 (10)
C15	0.0414 (12)	0.0426 (11)	0.0634 (14)	0.0008 (10)	0.0032 (10)	0.0021 (10)
C13	0.0481 (12)	0.0482 (12)	0.0696 (15)	−0.0022 (12)	−0.0060 (12)	0.0048 (11)
C8	0.0405 (11)	0.0570 (14)	0.0604 (14)	0.0020 (11)	0.0069 (11)	0.0016 (11)
C1	0.0630 (16)	0.0617 (15)	0.0702 (17)	0.0093 (14)	0.0084 (14)	0.0007 (13)
C12	0.0431 (12)	0.0516 (13)	0.0862 (18)	0.0046 (11)	−0.0021 (13)	0.0033 (13)
C11	0.0423 (11)	0.0507 (13)	0.0739 (16)	−0.0010 (11)	0.0092 (11)	−0.0019 (12)
C6	0.0500 (13)	0.0459 (11)	0.0558 (13)	−0.0033 (11)	0.0016 (11)	−0.0053 (10)
C5	0.0538 (14)	0.0686 (16)	0.0658 (16)	0.0088 (14)	−0.0002 (13)	−0.0047 (12)
C16	0.0697 (17)	0.0822 (19)	0.0605 (14)	0.0098 (17)	−0.0012 (14)	−0.0001 (14)
C4	0.0721 (18)	0.0784 (18)	0.0648 (16)	0.0102 (17)	−0.0104 (15)	−0.0002 (14)
C3	0.095 (2)	0.0701 (17)	0.0569 (15)	0.0028 (18)	−0.0021 (16)	−0.0022 (13)
C2	0.0784 (19)	0.0758 (18)	0.0644 (16)	0.0096 (17)	0.0163 (15)	−0.0032 (14)

Geometric parameters (Å, º) top

N—C7	1.314 (3)	C1—C6	1.386 (3)
N—O	1.412 (2)	C1—H1	0.9300
O—C9	1.341 (3)	C12—C11	1.378 (3)
C9—C8	1.360 (3)	C12—H12	0.9300
C9—C10	1.457 (3)	C11—H11	0.9300
C10—C15	1.394 (3)	C6—C5	1.378 (3)
C10—C11	1.397 (3)	C5—C4	1.372 (4)
C14—C15	1.379 (3)	C5—H5	0.9300
C14—C13	1.387 (3)	C16—H16A	0.9600
C14—C16	1.511 (3)	C16—H16B	0.9600
C7—C8	1.383 (3)	C16—H16C	0.9600
C7—C6	1.474 (3)	C4—C3	1.366 (4)
C15—H15	0.9300	C4—H4	0.9300
C13—C12	1.379 (4)	C3—C2	1.367 (4)
C13—H13	0.9300	C3—H3	0.9300
C8—H8	0.9300	C2—H2	0.9300
C1—C2	1.378 (4)

C7—N—O	106.11 (18)	C11—C12—H12	119.8
C9—O—N	107.76 (18)	C13—C12—H12	119.8
O—C9—C8	109.4 (2)	C12—C11—C10	119.9 (2)
O—C9—C10	116.8 (2)	C12—C11—H11	120.0
C8—C9—C10	133.8 (2)	C10—C11—H11	120.0
C15—C10—C11	118.5 (2)	C5—C6—C1	119.0 (2)
C15—C10—C9	121.2 (2)	C5—C6—C7	121.3 (2)
C11—C10—C9	120.4 (2)	C1—C6—C7	119.7 (2)
C15—C14—C13	118.3 (2)	C4—C5—C6	120.4 (2)
C15—C14—C16	120.6 (2)	C4—C5—H5	119.8
C13—C14—C16	121.2 (2)	C6—C5—H5	119.8
N—C7—C8	111.1 (2)	C14—C16—H16A	109.5
N—C7—C6	118.0 (2)	C14—C16—H16B	109.5
C8—C7—C6	130.9 (2)	H16A—C16—H16B	109.5
C14—C15—C10	121.9 (2)	C14—C16—H16C	109.5
C14—C15—H15	119.0	H16A—C16—H16C	109.5
C10—C15—H15	119.0	H16B—C16—H16C	109.5
C12—C13—C14	120.9 (2)	C3—C4—C5	120.1 (3)
C12—C13—H13	119.5	C3—C4—H4	119.9
C14—C13—H13	119.5	C5—C4—H4	119.9
C9—C8—C7	105.7 (2)	C4—C3—C2	120.3 (3)
C9—C8—H8	127.2	C4—C3—H3	119.8
C7—C8—H8	127.2	C2—C3—H3	119.8
C2—C1—C6	120.1 (3)	C3—C2—C1	120.0 (3)
C2—C1—H1	120.0	C3—C2—H2	120.0
C6—C1—H1	120.0	C1—C2—H2	120.0
C11—C12—C13	120.5 (2)

C7—N—O—C9	0.3 (3)	C6—C7—C8—C9	179.6 (2)
N—O—C9—C8	−0.2 (3)	C14—C13—C12—C11	−0.1 (4)
N—O—C9—C10	179.04 (18)	C13—C12—C11—C10	−1.0 (4)
O—C9—C10—C15	−16.3 (3)	C15—C10—C11—C12	1.4 (3)
C8—C9—C10—C15	162.8 (3)	C9—C10—C11—C12	−178.9 (2)
O—C9—C10—C11	164.0 (2)	C2—C1—C6—C5	0.1 (4)
C8—C9—C10—C11	−16.9 (4)	C2—C1—C6—C7	178.7 (3)
O—N—C7—C8	−0.2 (3)	N—C7—C6—C5	16.0 (3)
O—N—C7—C6	−179.81 (18)	C8—C7—C6—C5	−163.5 (3)
C13—C14—C15—C10	−0.3 (3)	N—C7—C6—C1	−162.6 (2)
C16—C14—C15—C10	179.6 (2)	C8—C7—C6—C1	17.9 (4)
C11—C10—C15—C14	−0.8 (3)	C1—C6—C5—C4	−0.1 (4)
C9—C10—C15—C14	179.6 (2)	C7—C6—C5—C4	−178.7 (2)
C15—C14—C13—C12	0.7 (3)	C6—C5—C4—C3	0.1 (4)
C16—C14—C13—C12	−179.2 (2)	C5—C4—C3—C2	−0.2 (4)
O—C9—C8—C7	0.1 (3)	C4—C3—C2—C1	0.2 (4)
C10—C9—C8—C7	−179.0 (2)	C6—C1—C2—C3	−0.1 (4)
N—C7—C8—C9	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O	0.93	2.49	2.803 (3)	100

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO
M_r	235.27
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.8052 (2), 7.7010 (3), 27.4363 (8)
V (Å³)	1226.56 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14583, 1599, 1302
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.08
No. of reflections	1599
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

BB thanks Dr Babu Varghese, SAIF, IIT–Madras, India, for his help with the data collection.

References

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