5-(1-Cyclo-hexen-1-yl)-3-(4-methoxy-phen-yl)isoxazole.

In the title compound, C(16)H(17)NO(2), the isoxazole ring makes a dihedral angle of 14.81 (13)° with the 4-methoxy-phenyl ring. Two atoms of the cyclo-hexene ring are disordered over two almost equally occupied positions [0.526 (13)/0.474 (13)]. The mol-ecular structure features a short intra-molecular C-H⋯O contact.

Related literature

For background to isoxazoles, see: Melo (2005 ▶). For their biological activities, see: Narlawar et al. (2008 ▶); Patrick et al. (2007 ▶); Taldone et al. (2008 ▶); Rizzi et al. (2008 ▶); Velaparthi et al. (2008 ▶). For synthetic details, see: Hansen et al. (2005 ▶).

Experimental

Crystal data

C16H17NO2

M = 255.31

Triclinic,

a = 5.8690 (11) Å

b = 10.9646 (19) Å

c = 11.481 (5) Å

α = 77.889 (2)°

β = 75.728 (5)°

γ = 80.262 (9)°

V = 694.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.20 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

4217 measured reflections

2467 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.14

2467 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010903/bt2910sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010903/bt2910Isup2.hkl

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

C16H17NO2	Z = 2
Mr = 255.31	F(000) = 272
Triclinic, P1	Dx = 1.221 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8690 (11) Å	Cell parameters from 2123 reflections
b = 10.9646 (19) Å	θ = 1.9–24.4°
c = 11.481 (5) Å	µ = 0.08 mm−1
α = 77.889 (2)°	T = 295 K
β = 75.728 (5)°	Block, yellow
γ = 80.262 (9)°	0.20 × 0.16 × 0.10 mm
V = 694.7 (4) Å3

Nonius KappaCCD area-detector diffractometer	2023 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
graphite	θmax = 25.2°, θmin = 3.6°
φ scans, and ω scans with κ offsets	h = 0→7
2467 measured reflections	k = −12→13
2467 independent reflections	l = −12→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.128P] where P = (Fo2 + 2Fc2)/3
2467 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3554 (2)	0.17491 (13)	−0.04016 (12)	0.0640 (4)
O2	−0.2921 (2)	0.60615 (14)	0.41851 (13)	0.0715 (4)
N1	0.3139 (3)	0.25243 (16)	0.04881 (15)	0.0628 (5)
C1	0.1547 (3)	0.10166 (16)	−0.16684 (15)	0.0495 (4)
C2	−0.0473 (4)	0.1345 (2)	−0.2317 (2)	0.0690 (6)
H2A	−0.0272	0.2116	−0.2907	0.083*	0.474 (13)
H2B	−0.1962	0.1473	−0.1734	0.083*	0.474 (13)
H2C	−0.0855	0.2253	−0.2471	0.083*	0.526 (13)
H2D	−0.1854	0.0998	−0.178	0.083*	0.526 (13)
C3A	−0.0493 (12)	0.0236 (11)	−0.2981 (9)	0.071 (2)	0.474 (13)
H3A1	−0.1043	−0.0477	−0.238	0.106*	0.474 (13)
H3A2	−0.1588	0.0494	−0.3523	0.106*	0.474 (13)
C4A	0.1966 (18)	−0.0159 (11)	−0.3718 (9)	0.081 (2)	0.474 (13)
H4A1	0.1885	−0.0773	−0.4199	0.121*	0.474 (13)
H4A2	0.2607	0.0564	−0.4266	0.121*	0.474 (13)
C5	0.3446 (4)	−0.0697 (2)	−0.2859 (2)	0.0758 (6)
H5A	0.5079	−0.0816	−0.3303	0.091*	0.474 (13)
H5B	0.2998	−0.1517	−0.245	0.091*	0.474 (13)
H5C	0.3818	−0.1576	−0.252	0.091*	0.526 (13)
H5D	0.4711	−0.0468	−0.3556	0.091*	0.526 (13)
C6	0.3280 (3)	0.00944 (18)	−0.19162 (18)	0.0607 (5)
H6	0.4466	−0.007	−0.1476	0.073*
C7	0.1488 (3)	0.17676 (16)	−0.07484 (15)	0.0483 (4)
C8	−0.0224 (3)	0.25240 (16)	−0.01282 (15)	0.0494 (4)
H8	−0.1798	0.2716	−0.0194	0.059*
C9	0.0881 (3)	0.29654 (16)	0.06460 (16)	0.0475 (4)
C10	−0.0167 (3)	0.37884 (16)	0.15521 (15)	0.0470 (4)
C11	−0.2372 (3)	0.44858 (17)	0.15767 (16)	0.0534 (5)
H11	−0.3215	0.4431	0.1006	0.064*
C12	−0.3358 (3)	0.52620 (17)	0.24271 (17)	0.0550 (5)
H12	−0.4838	0.5726	0.242	0.066*
C13	−0.2127 (3)	0.53436 (17)	0.32878 (17)	0.0539 (5)
C14	0.0074 (3)	0.4641 (2)	0.32840 (19)	0.0650 (5)
H14	0.0903	0.4686	0.3864	0.078*
C15	0.1035 (3)	0.38833 (19)	0.24361 (18)	0.0605 (5)
H15	0.2516	0.3422	0.2446	0.073*
C16	−0.5130 (4)	0.6839 (2)	0.4212 (2)	0.0756 (6)
H16A	−0.5046	0.7435	0.3464	0.113*
H16B	−0.5476	0.7279	0.4887	0.113*
H16C	−0.6359	0.6327	0.4303	0.113*
C3B	0.0006 (13)	0.0880 (9)	−0.3512 (8)	0.0726 (19)	0.526 (13)
H3B1	0.1138	0.1355	−0.4124	0.087*	0.526 (13)
H3B2	−0.1448	0.0981	−0.3799	0.087*	0.526 (13)
C4B	0.0995 (17)	−0.0499 (7)	−0.3290 (8)	0.0731 (19)	0.526 (13)
H4B1	0.1244	−0.0833	−0.4036	0.11*	0.526 (13)
H4B2	−0.0147	−0.0961	−0.267	0.11*	0.526 (13)

	U11	U22	U33	U12	U13	U23
O1	0.0476 (7)	0.0832 (9)	0.0673 (9)	0.0055 (6)	−0.0185 (6)	−0.0305 (7)
O2	0.0740 (9)	0.0768 (9)	0.0685 (9)	0.0023 (7)	−0.0157 (7)	−0.0325 (8)
N1	0.0514 (9)	0.0822 (11)	0.0622 (10)	0.0027 (8)	−0.0193 (7)	−0.0297 (9)
C1	0.0466 (10)	0.0553 (10)	0.0451 (10)	−0.0090 (8)	−0.0065 (7)	−0.0073 (8)
C2	0.0610 (12)	0.0819 (14)	0.0743 (14)	−0.0005 (10)	−0.0252 (10)	−0.0304 (12)
C3A	0.062 (3)	0.087 (6)	0.075 (5)	−0.004 (3)	−0.027 (3)	−0.029 (4)
C4A	0.079 (5)	0.106 (6)	0.063 (5)	−0.008 (4)	−0.010 (4)	−0.039 (4)
C5	0.0782 (14)	0.0745 (14)	0.0755 (15)	0.0014 (11)	−0.0122 (12)	−0.0294 (12)
C6	0.0594 (11)	0.0648 (12)	0.0584 (12)	−0.0014 (9)	−0.0147 (9)	−0.0146 (10)
C7	0.0430 (9)	0.0559 (10)	0.0456 (10)	−0.0077 (7)	−0.0113 (7)	−0.0045 (8)
C8	0.0406 (9)	0.0601 (11)	0.0484 (10)	−0.0046 (7)	−0.0113 (7)	−0.0111 (8)
C9	0.0432 (9)	0.0525 (10)	0.0451 (10)	−0.0071 (7)	−0.0110 (7)	−0.0023 (8)
C10	0.0439 (9)	0.0529 (10)	0.0437 (10)	−0.0100 (7)	−0.0086 (7)	−0.0055 (8)
C11	0.0510 (10)	0.0624 (11)	0.0494 (11)	−0.0056 (8)	−0.0173 (8)	−0.0090 (9)
C12	0.0481 (10)	0.0588 (11)	0.0555 (11)	0.0009 (8)	−0.0131 (8)	−0.0084 (9)
C13	0.0568 (11)	0.0542 (11)	0.0501 (11)	−0.0103 (8)	−0.0083 (8)	−0.0092 (9)
C14	0.0571 (11)	0.0840 (14)	0.0632 (13)	−0.0055 (10)	−0.0233 (9)	−0.0242 (11)
C15	0.0470 (10)	0.0772 (13)	0.0627 (13)	0.0006 (9)	−0.0188 (9)	−0.0227 (10)
C16	0.0791 (14)	0.0645 (13)	0.0747 (15)	0.0025 (11)	−0.0032 (11)	−0.0189 (11)
C3B	0.090 (4)	0.072 (4)	0.066 (4)	−0.002 (3)	−0.035 (3)	−0.019 (3)
C4B	0.087 (5)	0.072 (4)	0.067 (4)	−0.003 (3)	−0.020 (4)	−0.029 (3)

O1—C7	1.362 (2)	C5—H5D	0.97
O1—N1	1.413 (2)	C6—H6	0.93
O2—C13	1.370 (2)	C7—C8	1.348 (2)
O2—C16	1.424 (2)	C8—C9	1.420 (2)
N1—C9	1.313 (2)	C8—H8	0.93
C1—C6	1.330 (2)	C9—C10	1.472 (2)
C1—C7	1.460 (3)	C10—C11	1.384 (2)
C1—C2	1.506 (3)	C10—C15	1.400 (3)
C2—C3B	1.509 (6)	C11—C12	1.384 (2)
C2—C3A	1.569 (7)	C11—H11	0.93
C2—H2A	0.97	C12—C13	1.385 (3)
C2—H2B	0.97	C12—H12	0.93
C2—H2C	0.97	C13—C14	1.387 (3)
C2—H2D	0.97	C14—C15	1.366 (3)
C3A—C4A	1.525 (13)	C14—H14	0.93
C3A—H3A1	0.97	C15—H15	0.93
C3A—H3A2	0.97	C16—H16A	0.96
C4A—C5	1.442 (9)	C16—H16B	0.96
C4A—H4A1	0.97	C16—H16C	0.96
C4A—H4A2	0.97	C3B—C4B	1.517 (12)
C5—C6	1.499 (3)	C3B—H3B1	0.97
C5—C4B	1.601 (8)	C3B—H3B2	0.97
C5—H5A	0.97	C4B—H4B1	0.97
C5—H5B	0.97	C4B—H4B2	0.97
C5—H5C	0.97
C7—O1—N1	108.69 (13)	C4B—C5—H5D	109.6
C13—O2—C16	118.24 (16)	H5B—C5—H5D	130.2
C9—N1—O1	105.65 (13)	H5C—C5—H5D	108.1
C6—C1—C7	121.93 (16)	C1—C6—C5	124.23 (19)
C6—C1—C2	121.99 (18)	C1—C6—H6	117.9
C7—C1—C2	116.08 (15)	C5—C6—H6	117.9
C1—C2—C3B	114.7 (3)	C8—C7—O1	108.99 (15)
C1—C2—C3A	108.3 (3)	C8—C7—C1	133.87 (16)
C1—C2—H2A	110	O1—C7—C1	117.14 (15)
C3B—C2—H2A	78	C7—C8—C9	105.51 (15)
C3A—C2—H2A	110	C7—C8—H8	127.2
C1—C2—H2B	110	C9—C8—H8	127.2
C3B—C2—H2B	129.1	N1—C9—C8	111.14 (16)
C3A—C2—H2B	110	N1—C9—C10	119.80 (15)
H2A—C2—H2B	108.4	C8—C9—C10	129.05 (15)
C1—C2—H2C	108.6	C11—C10—C15	117.38 (17)
C3B—C2—H2C	108.6	C11—C10—C9	121.84 (15)
C3A—C2—H2C	136.3	C15—C10—C9	120.78 (16)
H2B—C2—H2C	77.8	C12—C11—C10	121.89 (16)
C1—C2—H2D	108.6	C12—C11—H11	119.1
C3B—C2—H2D	108.6	C10—C11—H11	119.1
C3A—C2—H2D	81.5	C11—C12—C13	119.56 (16)
H2A—C2—H2D	133	C11—C12—H12	120.2
H2C—C2—H2D	107.6	C13—C12—H12	120.2
C4A—C3A—C2	111.4 (8)	O2—C13—C12	125.20 (17)
C4A—C3A—H3A1	109.3	O2—C13—C14	115.51 (16)
C2—C3A—H3A1	109.3	C12—C13—C14	119.28 (18)
C4A—C3A—H3A2	109.3	C15—C14—C13	120.63 (17)
C2—C3A—H3A2	109.3	C15—C14—H14	119.7
H3A1—C3A—H3A2	108	C13—C14—H14	119.7
C5—C4A—C3A	107.3 (8)	C14—C15—C10	121.24 (18)
C5—C4A—H4A1	110.3	C14—C15—H15	119.4
C3A—C4A—H4A1	110.3	C10—C15—H15	119.4
C5—C4A—H4A2	110.3	O2—C16—H16A	109.5
C3A—C4A—H4A2	110.3	O2—C16—H16B	109.5
H4A1—C4A—H4A2	108.5	H16A—C16—H16B	109.5
C4A—C5—C6	113.5 (4)	O2—C16—H16C	109.5
C6—C5—C4B	110.4 (3)	H16A—C16—H16C	109.5
C4A—C5—H5A	108.9	H16B—C16—H16C	109.5
C6—C5—H5A	108.9	C2—C3B—C4B	107.7 (7)
C4B—C5—H5A	131.7	C2—C3B—H3B1	110.2
C4A—C5—H5B	108.9	C4B—C3B—H3B1	110.2
C6—C5—H5B	108.9	C2—C3B—H3B2	110.2
C4B—C5—H5B	84.8	C4B—C3B—H3B2	110.2
H5A—C5—H5B	107.7	H3B1—C3B—H3B2	108.5
C4A—C5—H5C	128.3	C3B—C4B—C5	111.5 (7)
C6—C5—H5C	109.6	C3B—C4B—H4B1	109.3
C4B—C5—H5C	109.6	C5—C4B—H4B1	109.3
H5A—C5—H5C	81.9	C3B—C4B—H4B2	109.3
C4A—C5—H5D	83	C5—C4B—H4B2	109.3
C6—C5—H5D	109.6	H4B1—C4B—H4B2	108
C7—O1—N1—C9	0.36 (19)	C7—C8—C9—N1	1.2 (2)
C6—C1—C2—C3B	−19.4 (5)	C7—C8—C9—C10	−177.85 (16)
C7—C1—C2—C3B	160.8 (5)	N1—C9—C10—C11	166.10 (16)
C6—C1—C2—C3A	15.2 (5)	C8—C9—C10—C11	−14.9 (3)
C7—C1—C2—C3A	−164.6 (5)	N1—C9—C10—C15	−14.6 (3)
C1—C2—C3A—C4A	−48.6 (11)	C8—C9—C10—C15	164.40 (18)
C3B—C2—C3A—C4A	58.7 (9)	C15—C10—C11—C12	0.8 (3)
C2—C3A—C4A—C5	66.8 (13)	C9—C10—C11—C12	−179.88 (15)
C3A—C4A—C5—C6	−48.4 (12)	C10—C11—C12—C13	−0.5 (3)
C3A—C4A—C5—C4B	41.0 (10)	C16—O2—C13—C12	−3.3 (3)
C7—C1—C6—C5	−179.31 (18)	C16—O2—C13—C14	177.82 (17)
C2—C1—C6—C5	0.9 (3)	C11—C12—C13—O2	−179.06 (16)
C4A—C5—C6—C1	16.8 (6)	C11—C12—C13—C14	−0.2 (3)
C4B—C5—C6—C1	−13.1 (5)	O2—C13—C14—C15	179.53 (17)
N1—O1—C7—C8	0.39 (19)	C12—C13—C14—C15	0.6 (3)
N1—O1—C7—C1	−179.91 (14)	C13—C14—C15—C10	−0.3 (3)
C6—C1—C7—C8	−162.0 (2)	C11—C10—C15—C14	−0.4 (3)
C2—C1—C7—C8	17.8 (3)	C9—C10—C15—C14	−179.76 (17)
C6—C1—C7—O1	18.4 (2)	C1—C2—C3B—C4B	49.0 (10)
C2—C1—C7—O1	−161.79 (16)	C3A—C2—C3B—C4B	−36.8 (7)
O1—C7—C8—C9	−0.93 (19)	C2—C3B—C4B—C5	−61.8 (11)
C1—C7—C8—C9	179.44 (18)	C4A—C5—C4B—C3B	−57.8 (11)
O1—N1—C9—C8	−1.0 (2)	C6—C5—C4B—C3B	44.2 (10)
O1—N1—C9—C10	178.20 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.48	2.811 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.48	2.811 (3)	101