3,5-Bis(4-meth-oxy-phen-yl)-4,5-dihydro-isoxazole.

In the title compound, C(17)H(17)NO(3), the five-membered isoxazoline ring adopts an envelope conformation with the chiral C atom at the flap position and 0.133 (2) Å out of the mean plane formed by the other four atoms. The two benzene rings form dihedral angles of 6.05 (5) and 81.52 (5)° with the C-C-N-O plane of the isoxazoline ring. The crystal structure is stabilized by weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For medical uses of isoxazole derivatives, see: Sperry & Wright (2005 ▶). For their biological activity, see; Boyd (1991 ▶); Lang & Lin (1984 ▶). For related structures, see; Baktır et al. (2011a ▶,b ▶); Chopra et al. (2006 ▶); Dardouri et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Guo et al. (2006 ▶); Jasinski et al. (2010 ▶); Ko et al. (2011 ▶); Samshuddin et al. (2010 ▶). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C17H17NO3

M = 283.32

Orthorhombic,

a = 10.5071 (7) Å

b = 8.4023 (5) Å

c = 32.6662 (19) Å

V = 2883.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.42 × 0.36 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.967, T max = 1.000

13952 measured reflections

4821 independent reflections

2738 reflections with i > 2σ(i)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.156

S = 1.06

4821 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026833/im2301sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026833/im2301Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026833/im2301Isup3.cml

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

C17H17NO3	F(000) = 1200
Mr = 283.32	Dx = 1.305 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2593 reflections
a = 10.5071 (7) Å	θ = 5.2–32.6°
b = 8.4023 (5) Å	µ = 0.09 mm−1
c = 32.6662 (19) Å	T = 295 K
V = 2883.9 (3) Å3	Triangular plate, colourless
Z = 8	0.42 × 0.36 × 0.16 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4821 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2738 reflections with i > 2σ(i)
graphite	Rint = 0.046
Detector resolution: 10.5081 pixels mm-1	θmax = 32.7°, θmin = 5.2°
ω scans	h = −12→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −10→12
Tmin = 0.967, Tmax = 1.000	l = −29→46
13952 measured reflections

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.4739P] where P = (Fo2 + 2Fc2)/3
4821 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
O1	0.70804 (13)	0.51832 (16)	0.43065 (4)	0.0604 (5)
O1A	0.63367 (15)	0.77980 (18)	0.25241 (4)	0.0702 (5)
O1B	0.62961 (12)	0.83077 (16)	0.65053 (4)	0.0603 (5)
N1	0.72185 (15)	0.54460 (19)	0.47317 (4)	0.0554 (5)
C1	0.58593 (17)	0.5848 (2)	0.41763 (5)	0.0480 (6)
C1A	0.59901 (16)	0.6424 (2)	0.37429 (5)	0.0424 (5)
C1B	0.63231 (14)	0.69607 (18)	0.52798 (5)	0.0381 (5)
C2	0.55553 (17)	0.7045 (2)	0.45099 (5)	0.0487 (6)
C2A	0.51887 (17)	0.5861 (2)	0.34384 (6)	0.0534 (6)
C2B	0.53722 (15)	0.7969 (2)	0.54218 (5)	0.0420 (5)
C3	0.63763 (14)	0.64427 (19)	0.48509 (5)	0.0392 (5)
C3A	0.53294 (18)	0.6342 (2)	0.30376 (6)	0.0588 (7)
C3B	0.53190 (15)	0.8445 (2)	0.58282 (5)	0.0440 (5)
C4A	0.62771 (17)	0.7403 (2)	0.29317 (5)	0.0476 (6)
C4B	0.62455 (15)	0.7929 (2)	0.60983 (5)	0.0435 (5)
C5A	0.70837 (17)	0.7983 (2)	0.32303 (5)	0.0485 (6)
C5B	0.71995 (16)	0.6916 (2)	0.59621 (5)	0.0502 (6)
C6A	0.69329 (16)	0.7490 (2)	0.36319 (5)	0.0472 (5)
C6B	0.72320 (15)	0.6433 (2)	0.55609 (5)	0.0459 (6)
C7A	0.7369 (2)	0.8744 (3)	0.23880 (6)	0.0751 (9)
C7B	0.53076 (19)	0.9273 (3)	0.66684 (6)	0.0651 (8)
H2AA	0.45450	0.51470	0.35060	0.0640*
H1A	0.52180	0.50020	0.41830	0.0580*
H3AA	0.47830	0.59510	0.28370	0.0710*
H2A	0.57900	0.81170	0.44300	0.0580*
H2B	0.46610	0.70220	0.45830	0.0580*
H5AA	0.77240	0.87000	0.31620	0.0580*
H6AA	0.74780	0.78840	0.38320	0.0570*
H7AA	0.73380	0.88390	0.20950	0.1130*
H7AB	0.81560	0.82520	0.24670	0.1130*
H7AC	0.73120	0.97830	0.25090	0.1130*
H2BA	0.47560	0.83330	0.52400	0.0500*
H3BA	0.46660	0.91050	0.59180	0.0530*
H5BA	0.78200	0.65630	0.61440	0.0600*
H6BA	0.78700	0.57420	0.54750	0.0550*
H7BA	0.54280	0.93930	0.69580	0.0980*
H7BB	0.45000	0.87780	0.66170	0.0980*
H7BC	0.53280	1.03010	0.65400	0.0980*

	U11	U22	U33	U12	U13	U23
O1	0.0765 (9)	0.0589 (8)	0.0457 (7)	0.0266 (7)	0.0012 (6)	−0.0037 (6)
O1A	0.0859 (10)	0.0801 (10)	0.0445 (8)	−0.0125 (8)	−0.0025 (7)	0.0053 (7)
O1B	0.0668 (8)	0.0680 (9)	0.0461 (7)	0.0106 (7)	−0.0018 (6)	−0.0049 (6)
N1	0.0640 (10)	0.0565 (10)	0.0458 (8)	0.0209 (8)	0.0000 (7)	0.0006 (7)
C1	0.0512 (10)	0.0445 (10)	0.0484 (10)	−0.0028 (8)	−0.0005 (8)	0.0025 (7)
C1A	0.0459 (9)	0.0381 (9)	0.0433 (9)	0.0013 (7)	0.0011 (7)	−0.0018 (7)
C1B	0.0353 (8)	0.0358 (8)	0.0431 (9)	−0.0013 (7)	0.0019 (7)	0.0057 (6)
C2	0.0467 (9)	0.0551 (11)	0.0442 (9)	0.0109 (8)	0.0026 (7)	0.0033 (8)
C2A	0.0503 (10)	0.0533 (11)	0.0565 (11)	−0.0148 (9)	−0.0028 (8)	0.0009 (8)
C2B	0.0387 (8)	0.0410 (9)	0.0463 (9)	0.0046 (7)	−0.0007 (7)	0.0084 (7)
C3	0.0371 (8)	0.0354 (8)	0.0452 (9)	−0.0005 (7)	0.0028 (7)	0.0051 (6)
C3A	0.0607 (12)	0.0630 (12)	0.0528 (11)	−0.0120 (10)	−0.0144 (9)	−0.0034 (9)
C3B	0.0428 (9)	0.0387 (9)	0.0504 (10)	0.0047 (7)	0.0067 (7)	0.0044 (7)
C4A	0.0534 (10)	0.0480 (10)	0.0413 (9)	0.0038 (9)	0.0011 (7)	−0.0012 (7)
C4B	0.0462 (9)	0.0427 (9)	0.0417 (9)	−0.0033 (8)	0.0020 (7)	0.0031 (7)
C5A	0.0493 (10)	0.0458 (10)	0.0505 (10)	−0.0062 (8)	0.0029 (8)	0.0004 (7)
C5B	0.0439 (10)	0.0568 (11)	0.0500 (10)	0.0083 (8)	−0.0081 (7)	0.0044 (8)
C6A	0.0482 (9)	0.0480 (10)	0.0454 (9)	−0.0055 (8)	−0.0050 (7)	−0.0055 (7)
C6B	0.0384 (9)	0.0483 (10)	0.0511 (10)	0.0087 (8)	0.0017 (7)	0.0024 (8)
C7A	0.0860 (16)	0.0809 (16)	0.0584 (13)	−0.0076 (13)	0.0103 (11)	0.0144 (11)
C7B	0.0696 (13)	0.0732 (14)	0.0524 (12)	0.0015 (11)	0.0105 (9)	−0.0100 (10)

O1—N1	1.4139 (19)	C4B—C5B	1.388 (2)
O1—C1	1.463 (2)	C5A—C6A	1.385 (2)
O1A—C4A	1.374 (2)	C5B—C6B	1.372 (2)
O1A—C7A	1.416 (3)	C1—H1A	0.9800
O1B—C4B	1.368 (2)	C2—H2A	0.9700
O1B—C7B	1.421 (3)	C2—H2B	0.9700
N1—C3	1.279 (2)	C2A—H2AA	0.9300
C1—C1A	1.503 (2)	C2B—H2BA	0.9300
C1—C2	1.517 (2)	C3A—H3AA	0.9300
C1A—C2A	1.386 (2)	C3B—H3BA	0.9300
C1A—C6A	1.384 (2)	C5A—H5AA	0.9300
C1B—C2B	1.390 (2)	C5B—H5BA	0.9300
C1B—C3	1.468 (2)	C6A—H6AA	0.9300
C1B—C6B	1.397 (2)	C6B—H6BA	0.9300
C2—C3	1.497 (2)	C7A—H7AA	0.9600
C2A—C3A	1.378 (3)	C7A—H7AB	0.9600
C2B—C3B	1.388 (2)	C7A—H7AC	0.9600
C3A—C4A	1.381 (3)	C7B—H7BA	0.9600
C3B—C4B	1.384 (2)	C7B—H7BB	0.9600
C4A—C5A	1.381 (2)	C7B—H7BC	0.9600
N1—O1—C1	108.43 (13)	C1—C2—H2A	112.00
C4A—O1A—C7A	118.35 (15)	C1—C2—H2B	112.00
C4B—O1B—C7B	117.94 (14)	C3—C2—H2A	112.00
O1—N1—C3	109.29 (14)	C3—C2—H2B	112.00
O1—C1—C1A	108.47 (14)	H2A—C2—H2B	109.00
O1—C1—C2	103.24 (13)	C1A—C2A—H2AA	119.00
C1A—C1—C2	118.86 (14)	C3A—C2A—H2AA	119.00
C1—C1A—C2A	120.70 (15)	C1B—C2B—H2BA	119.00
C1—C1A—C6A	121.39 (15)	C3B—C2B—H2BA	119.00
C2A—C1A—C6A	117.88 (15)	C2A—C3A—H3AA	120.00
C2B—C1B—C3	121.78 (14)	C4A—C3A—H3AA	120.00
C2B—C1B—C6B	117.75 (15)	C2B—C3B—H3BA	120.00
C3—C1B—C6B	120.47 (14)	C4B—C3B—H3BA	120.00
C1—C2—C3	100.90 (13)	C4A—C5A—H5AA	120.00
C1A—C2A—C3A	121.09 (16)	C6A—C5A—H5AA	120.00
C1B—C2B—C3B	121.60 (15)	C4B—C5B—H5BA	120.00
N1—C3—C1B	120.73 (14)	C6B—C5B—H5BA	120.00
N1—C3—C2	113.17 (14)	C1A—C6A—H6AA	119.00
C1B—C3—C2	126.01 (14)	C5A—C6A—H6AA	119.00
C2A—C3A—C4A	120.32 (17)	C1B—C6B—H6BA	120.00
C2B—C3B—C4B	119.44 (15)	C5B—C6B—H6BA	119.00
O1A—C4A—C3A	115.58 (16)	O1A—C7A—H7AA	109.00
O1A—C4A—C5A	124.85 (16)	O1A—C7A—H7AB	109.00
C3A—C4A—C5A	119.57 (16)	O1A—C7A—H7AC	109.00
O1B—C4B—C3B	125.04 (15)	H7AA—C7A—H7AB	109.00
O1B—C4B—C5B	115.21 (14)	H7AA—C7A—H7AC	109.00
C3B—C4B—C5B	119.72 (15)	H7AB—C7A—H7AC	110.00
C4A—C5A—C6A	119.56 (16)	O1B—C7B—H7BA	109.00
C4B—C5B—C6B	120.35 (15)	O1B—C7B—H7BB	109.00
C1A—C6A—C5A	121.58 (16)	O1B—C7B—H7BC	109.00
C1B—C6B—C5B	121.12 (15)	H7BA—C7B—H7BB	110.00
O1—C1—H1A	109.00	H7BA—C7B—H7BC	109.00
C1A—C1—H1A	109.00	H7BB—C7B—H7BC	109.00
C2—C1—H1A	109.00
C1—O1—N1—C3	−12.91 (18)	C2B—C1B—C3—N1	−176.15 (16)
N1—O1—C1—C1A	148.33 (13)	C2B—C1B—C3—C2	7.6 (2)
N1—O1—C1—C2	21.37 (16)	C6B—C1B—C3—N1	3.2 (2)
C7A—O1A—C4A—C3A	−173.31 (17)	C6B—C1B—C3—C2	−173.08 (15)
C7A—O1A—C4A—C5A	6.5 (3)	C2B—C1B—C6B—C5B	−1.1 (2)
C7B—O1B—C4B—C3B	1.7 (3)	C3—C1B—C6B—C5B	179.54 (15)
C7B—O1B—C4B—C5B	−176.75 (16)	C1—C2—C3—N1	14.78 (19)
O1—N1—C3—C1B	−178.53 (14)	C1—C2—C3—C1B	−168.71 (15)
O1—N1—C3—C2	−1.81 (19)	C1A—C2A—C3A—C4A	−0.1 (3)
O1—C1—C1A—C2A	123.44 (17)	C1B—C2B—C3B—C4B	1.2 (2)
O1—C1—C1A—C6A	−54.6 (2)	C2A—C3A—C4A—O1A	179.75 (16)
C2—C1—C1A—C2A	−119.19 (18)	C2A—C3A—C4A—C5A	−0.1 (3)
C2—C1—C1A—C6A	62.8 (2)	C2B—C3B—C4B—O1B	−179.72 (15)
O1—C1—C2—C3	−20.68 (16)	C2B—C3B—C4B—C5B	−1.4 (2)
C1A—C1—C2—C3	−140.76 (15)	O1A—C4A—C5A—C6A	−179.71 (16)
C1—C1A—C2A—C3A	−177.79 (16)	C3A—C4A—C5A—C6A	0.1 (3)
C6A—C1A—C2A—C3A	0.3 (3)	O1B—C4B—C5B—C6B	178.89 (15)
C1—C1A—C6A—C5A	177.80 (16)	C3B—C4B—C5B—C6B	0.4 (3)
C2A—C1A—C6A—C5A	−0.2 (3)	C4A—C5A—C6A—C1A	0.0 (3)
C3—C1B—C2B—C3B	179.44 (15)	C4B—C5B—C6B—C1B	0.9 (3)
C6B—C1B—C2B—C3B	0.1 (2)

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6AA···O1i	0.93	2.52	3.324 (2)	145
C1—H1A···Cg3ii	0.98	2.62	3.590 (2)	170
C6B—H6BA···Cg3iii	0.93	3.00	3.724 (2)	136
C7B—H7BC···Cg2iv	0.96	2.83	3.541 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6AA⋯O1i	0.93	2.52	3.324 (2)	145
C1—H1A⋯Cg3ii	0.98	2.62	3.590 (2)	170
C6B—H6BA⋯Cg3iii	0.93	3.00	3.724 (2)	136
C7B—H7BC⋯Cg2iv	0.96	2.83	3.541 (3)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .