Crystal structure of 5-(1-benzo-furan-2-yl)-3-(4-methyl-phen-yl)-4,5-di-hydro-1,2-oxazol-5-ol.

In the title compound, C18H15NO3, the isoxazole moiety adopts a shallow envelope conformation, with the C atom bearing the OH group displaced by 0.148 (1) Å from the mean plane through the other four atoms. The mean plane of this ring (all atoms) subtends dihedral angles of 87.19 (6) and 15.51 (7)° with the benzo-furan ring system (r.m.s. deviation = 0.007 Å) and the 4-methylphenyl ring, respectively. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, generating [001] C(5) chains, with adjacent mol-ecules in the chain related by c-glide symmetry. Weak C-H⋯O inter-actions link the chains into a three-dimensional network.

Related literature

For the biological and pharmaceutical properties of isoxazoles, see: Eddington et al. (2002 ▸); Lee et al. (2009 ▸); Rozman et al. (2002 ▸); Shin et al. (2005 ▸).

Experimental

Crystal data

C18H15NO3

M = 293.31

Monoclinic,

a = 10.2200 (15) Å

b = 14.2289 (19) Å

c = 10.2474 (15) Å

β = 93.058 (7)°

V = 1488.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

23993 measured reflections

3452 independent reflections

2829 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.03

3452 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011263/hb7438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011263/hb7438Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015011263/hb7438Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015011263/hb7438fig1.tif

Perspective diagram of the mol­ecule with 50% probability displacement ellipsoids.

Click here for additional data file.

a . DOI: 10.1107/S2056989015011263/hb7438fig2.tif

Packing diagram of the mol­ecule viewed down the a axis.

CCDC reference: 1405867

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H15NO3	F(000) = 616
Mr = 293.31	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3452 reflections
a = 10.2200 (15) Å	θ = 2.0–27.6°
b = 14.2289 (19) Å	µ = 0.09 mm−1
c = 10.2474 (15) Å	T = 293 K
β = 93.058 (7)°	Block, light yellow
V = 1488.1 (4) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	Rint = 0.047
ω and φ scans	θmax = 27.6°, θmin = 2.0°
23993 measured reflections	h = −13→13
3452 independent reflections	k = −18→18
2829 reflections with I > 2σ(I)	l = −13→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.3174P] where P = (Fo2 + 2Fc2)/3
3452 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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
O10	0.10420 (9)	0.22693 (6)	1.16214 (9)	0.0469 (3)
O13	0.01366 (9)	0.15474 (6)	0.97218 (9)	0.0424 (3)
O15	0.34411 (9)	0.12845 (9)	1.11345 (9)	0.0560 (4)
N9	0.02005 (11)	0.20392 (8)	1.26398 (11)	0.0442 (3)
C1	−0.10566 (14)	−0.02593 (9)	1.35272 (13)	0.0444 (4)
C2	−0.19545 (15)	−0.06737 (10)	1.43143 (14)	0.0490 (5)
C3	−0.27405 (13)	−0.01485 (10)	1.50880 (12)	0.0425 (4)
C4	−0.25865 (15)	0.08194 (11)	1.50733 (15)	0.0514 (5)
C5	−0.16973 (14)	0.12463 (10)	1.42932 (15)	0.0486 (4)
C6	−0.09233 (11)	0.07103 (8)	1.34970 (11)	0.0351 (3)
C7	−0.37282 (16)	−0.06253 (12)	1.59045 (16)	0.0589 (5)
C8	−0.00193 (12)	0.11530 (8)	1.26170 (11)	0.0346 (3)
C11	0.10936 (12)	0.14692 (8)	1.07341 (12)	0.0352 (3)
C12	0.07217 (12)	0.06513 (8)	1.15977 (11)	0.0358 (3)
C14	0.24379 (12)	0.14657 (9)	1.02232 (12)	0.0374 (3)
C16	0.45719 (14)	0.13194 (11)	1.04688 (14)	0.0498 (5)
C17	0.42854 (13)	0.15256 (9)	0.91647 (13)	0.0434 (4)
C18	0.28814 (13)	0.16133 (10)	0.90353 (13)	0.0431 (4)
C19	0.58217 (16)	0.11677 (16)	1.09931 (19)	0.0757 (7)
C20	0.68147 (16)	0.12359 (15)	1.0141 (2)	0.0747 (7)
C21	0.65735 (16)	0.14460 (13)	0.8845 (2)	0.0670 (6)
C22	0.53186 (17)	0.15950 (12)	0.83303 (17)	0.0608 (6)
H1	−0.05400	−0.06330	1.30160	0.0530*
H2	−0.20290	−0.13250	1.43210	0.0590*
H4	−0.30920	0.11890	1.56000	0.0620*
H5	−0.16150	0.18970	1.43000	0.0580*
H7A	−0.44440	−0.08530	1.53470	0.0880*
H7B	−0.40510	−0.01840	1.65190	0.0880*
H7C	−0.33190	−0.11430	1.63680	0.0880*
H12A	0.01720	0.02000	1.11180	0.0430*
H12B	0.14910	0.03350	1.19800	0.0430*
H13	0.02420	0.20390	0.93240	0.0640*
H18	0.23800	0.17470	0.82740	0.0520*
H19	0.59860	0.10270	1.18730	0.0910*
H20	0.76740	0.11370	1.04540	0.0900*
H21	0.72720	0.14890	0.83020	0.0800*
H22	0.51630	0.17380	0.74500	0.0730*

	U11	U22	U33	U12	U13	U23
O10	0.0539 (6)	0.0394 (5)	0.0492 (5)	−0.0152 (4)	0.0203 (4)	−0.0082 (4)
O13	0.0359 (5)	0.0471 (5)	0.0441 (5)	−0.0045 (4)	0.0002 (4)	0.0092 (4)
O15	0.0352 (5)	0.0961 (8)	0.0367 (5)	−0.0054 (5)	0.0013 (4)	0.0150 (5)
N9	0.0475 (6)	0.0416 (6)	0.0451 (6)	−0.0103 (5)	0.0175 (5)	−0.0081 (4)
C1	0.0504 (8)	0.0395 (7)	0.0445 (7)	0.0007 (5)	0.0132 (6)	−0.0021 (5)
C2	0.0581 (9)	0.0389 (7)	0.0508 (8)	−0.0041 (6)	0.0115 (7)	0.0050 (6)
C3	0.0395 (7)	0.0531 (8)	0.0351 (6)	−0.0041 (5)	0.0029 (5)	0.0083 (5)
C4	0.0497 (8)	0.0542 (8)	0.0522 (8)	−0.0015 (6)	0.0213 (7)	−0.0052 (6)
C5	0.0519 (8)	0.0382 (6)	0.0576 (8)	−0.0040 (6)	0.0204 (7)	−0.0060 (6)
C6	0.0332 (6)	0.0400 (6)	0.0322 (6)	−0.0031 (5)	0.0033 (5)	−0.0007 (5)
C7	0.0548 (9)	0.0719 (10)	0.0509 (8)	−0.0084 (7)	0.0120 (7)	0.0170 (7)
C8	0.0340 (6)	0.0375 (6)	0.0323 (6)	−0.0035 (5)	0.0029 (5)	−0.0026 (4)
C11	0.0346 (6)	0.0371 (6)	0.0340 (6)	−0.0041 (5)	0.0035 (5)	−0.0021 (4)
C12	0.0385 (6)	0.0357 (6)	0.0337 (6)	−0.0023 (5)	0.0064 (5)	−0.0014 (5)
C14	0.0348 (6)	0.0435 (6)	0.0338 (6)	−0.0034 (5)	0.0012 (5)	0.0015 (5)
C16	0.0354 (7)	0.0679 (9)	0.0464 (8)	−0.0041 (6)	0.0055 (6)	0.0068 (6)
C17	0.0405 (7)	0.0481 (7)	0.0422 (7)	0.0003 (5)	0.0085 (6)	−0.0001 (5)
C18	0.0394 (7)	0.0565 (8)	0.0337 (6)	0.0036 (6)	0.0040 (5)	0.0018 (5)
C19	0.0392 (9)	0.1234 (17)	0.0637 (11)	−0.0029 (9)	−0.0044 (8)	0.0191 (11)
C20	0.0354 (8)	0.0994 (14)	0.0893 (14)	−0.0008 (8)	0.0036 (8)	0.0033 (11)
C21	0.0447 (9)	0.0773 (12)	0.0813 (12)	−0.0022 (7)	0.0260 (8)	−0.0039 (9)
C22	0.0543 (9)	0.0773 (11)	0.0528 (9)	0.0024 (8)	0.0203 (7)	0.0011 (8)

O10—N9	1.4254 (15)	C16—C17	1.384 (2)
O10—C11	1.4597 (15)	C17—C18	1.4394 (19)
O13—C11	1.3917 (15)	C17—C22	1.397 (2)
O15—C14	1.3739 (16)	C19—C20	1.377 (3)
O15—C16	1.3739 (17)	C20—C21	1.371 (3)
O13—H13	0.8200	C21—C22	1.377 (2)
N9—C8	1.2808 (16)	C1—H1	0.9300
C1—C2	1.385 (2)	C2—H2	0.9300
C1—C6	1.3869 (17)	C4—H4	0.9300
C2—C3	1.379 (2)	C5—H5	0.9300
C3—C4	1.386 (2)	C7—H7A	0.9600
C3—C7	1.507 (2)	C7—H7B	0.9600
C4—C5	1.383 (2)	C7—H7C	0.9600
C5—C6	1.3935 (19)	C12—H12A	0.9700
C6—C8	1.4671 (16)	C12—H12B	0.9700
C8—C12	1.5028 (17)	C18—H18	0.9300
C11—C14	1.4961 (18)	C19—H19	0.9300
C11—C12	1.5225 (17)	C20—H20	0.9300
C14—C18	1.3380 (18)	C21—H21	0.9300
C16—C19	1.376 (2)	C22—H22	0.9300
N9—O10—C11	108.67 (9)	C16—C19—C20	116.20 (17)
C14—O15—C16	105.83 (10)	C19—C20—C21	121.95 (16)
C11—O13—H13	109.00	C20—C21—C22	121.36 (16)
O10—N9—C8	108.96 (10)	C17—C22—C21	118.27 (16)
C2—C1—C6	120.35 (12)	C2—C1—H1	120.00
C1—C2—C3	121.91 (13)	C6—C1—H1	120.00
C2—C3—C4	117.54 (13)	C1—C2—H2	119.00
C4—C3—C7	122.23 (13)	C3—C2—H2	119.00
C2—C3—C7	120.24 (13)	C3—C4—H4	119.00
C3—C4—C5	121.42 (14)	C5—C4—H4	119.00
C4—C5—C6	120.61 (13)	C4—C5—H5	120.00
C1—C6—C5	118.16 (11)	C6—C5—H5	120.00
C1—C6—C8	120.44 (11)	C3—C7—H7A	109.00
C5—C6—C8	121.38 (11)	C3—C7—H7B	109.00
N9—C8—C6	121.81 (11)	C3—C7—H7C	109.00
N9—C8—C12	112.70 (11)	H7A—C7—H7B	109.00
C6—C8—C12	125.48 (10)	H7A—C7—H7C	109.00
O10—C11—C12	102.46 (9)	H7B—C7—H7C	109.00
O10—C11—C14	106.56 (10)	C8—C12—H12A	112.00
O10—C11—O13	110.77 (9)	C8—C12—H12B	112.00
O13—C11—C14	111.19 (10)	C11—C12—H12A	112.00
C12—C11—C14	117.60 (10)	C11—C12—H12B	112.00
O13—C11—C12	107.88 (10)	H12A—C12—H12B	109.00
C8—C12—C11	101.05 (9)	C14—C18—H18	127.00
O15—C14—C18	111.78 (11)	C17—C18—H18	127.00
C11—C14—C18	132.83 (12)	C16—C19—H19	122.00
O15—C14—C11	115.38 (10)	C20—C19—H19	122.00
O15—C16—C17	110.29 (12)	C19—C20—H20	119.00
C17—C16—C19	123.67 (14)	C21—C20—H20	119.00
O15—C16—C19	126.04 (14)	C20—C21—H21	119.00
C16—C17—C18	105.42 (12)	C22—C21—H21	119.00
C18—C17—C22	136.03 (13)	C17—C22—H22	121.00
C16—C17—C22	118.55 (13)	C21—C22—H22	121.00
C14—C18—C17	106.68 (12)
C11—O10—N9—C8	13.54 (13)	C6—C8—C12—C11	161.79 (11)
N9—O10—C11—O13	91.49 (11)	O10—C11—C12—C8	23.18 (11)
N9—O10—C11—C12	−23.35 (12)	O13—C11—C12—C8	−93.75 (11)
N9—O10—C11—C14	−147.45 (9)	C14—C11—C12—C8	139.58 (11)
C16—O15—C14—C11	−179.68 (12)	O10—C11—C14—O15	66.25 (13)
C16—O15—C14—C18	−0.19 (16)	O10—C11—C14—C18	−113.10 (16)
C14—O15—C16—C17	0.43 (16)	O13—C11—C14—O15	−172.95 (11)
C14—O15—C16—C19	−179.12 (17)	O13—C11—C14—C18	7.7 (2)
O10—N9—C8—C6	−175.99 (10)	C12—C11—C14—O15	−47.91 (16)
O10—N9—C8—C12	3.06 (14)	C12—C11—C14—C18	132.74 (15)
C6—C1—C2—C3	0.0 (2)	O15—C14—C18—C17	−0.11 (16)
C2—C1—C6—C5	1.11 (19)	C11—C14—C18—C17	179.27 (13)
C2—C1—C6—C8	−177.02 (12)	O15—C16—C17—C18	−0.49 (16)
C1—C2—C3—C4	−1.2 (2)	O15—C16—C17—C22	179.71 (13)
C1—C2—C3—C7	178.48 (13)	C19—C16—C17—C18	179.07 (17)
C2—C3—C4—C5	1.3 (2)	C19—C16—C17—C22	−0.7 (2)
C7—C3—C4—C5	−178.39 (14)	O15—C16—C19—C20	179.82 (17)
C3—C4—C5—C6	−0.2 (2)	C17—C16—C19—C20	0.3 (3)
C4—C5—C6—C1	−1.0 (2)	C16—C17—C18—C14	0.36 (16)
C4—C5—C6—C8	177.08 (13)	C22—C17—C18—C14	−179.89 (16)
C1—C6—C8—N9	−174.48 (12)	C16—C17—C22—C21	0.6 (2)
C1—C6—C8—C12	6.60 (18)	C18—C17—C22—C21	−179.14 (16)
C5—C6—C8—N9	7.46 (19)	C16—C19—C20—C21	0.2 (3)
C5—C6—C8—C12	−171.46 (12)	C19—C20—C21—C22	−0.3 (3)
N9—C8—C12—C11	−17.21 (13)	C20—C21—C22—C17	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···N9i	0.82	2.17	2.9352 (15)	156
C2—H2···O10ii	0.93	2.46	3.2328 (17)	141
C7—H7C···O15iii	0.96	2.58	3.175 (2)	121
C18—H18···O10i	0.93	2.54	3.4183 (17)	158

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O13H13N9i	0.82	2.17	2.9352(15)	156
C2H2O10ii	0.93	2.46	3.2328(17)	141
C7H7CO15iii	0.96	2.58	3.175(2)	121
C18H18O10i	0.93	2.54	3.4183(17)	158

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