2-(2-Methoxy­phen­yl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Abstract

In the title mol­ecule, C₁₂H₁₅NO₂, the oxazole ring adopts an envelope conformation. Overall, the mol­ecule is approximately planar, the dihedral angle between the mean plane through all but the methyl­ene C atom of the five-membered ring and the aromatic ring being 8.6 (1)°. A weak C—H⋯O inter­action contributes to the stabilization of the crystal structure.

Related literature

For related crystal structures, see: Swaleh & Ziemer (2001 ▶); Rybakov et al. (2006 ▶).

Experimental

Crystal data

• C₁₂H₁₅NO₂

• M _r = 205.25

• Monoclinic,

• a = 8.1495 (2) Å

• b = 10.9369 (3) Å

• c = 12.0864 (3) Å

• β = 91.305 (3)°

• V = 1076.99 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 200 (2) K

• 0.39 × 0.31 × 0.24 mm

Data collection

• Oxford Diffraction Gemini diffractometer

• Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.717, T _max = 1.000 (expected range = 0.702–0.980)

• 34412 measured reflections

• 3740 independent reflections

• 2596 reflections with I > 2σ(I)

• R _int = 0.027

Refinement

• R[F ² > 2σ(F ²)] = 0.048

• wR(F ²) = 0.163

• S = 1.13

• 3740 reflections

• 139 parameters

• H-atom parameters constrained

• Δρ_max = 0.43 e Å⁻³

• Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O1	0.93	2.35	2.7136 (12)	103

supplementary crystallographic information

Comment

Swaleh and Ziemer (2001) reported the crystal structure of 2-[(2-phenyl-1,3-oxazol-4-yl)methyl]-2H-1,2,3-benzotriazole, wherein the phenyl and oxazole rings are essentially co-planar. Rybakov et al. (2006) reported the crystal structure of 5-(4-bromophenyl)-1,3-oxazol-2-amine, wherein the oxazole and the aromatic rings form a dihedral angle of 9.68 (7)°. In the title molecule, C₁₂H₁₅NO₂ (I), Fig. 1, the oxazole ring is in an envelope conformation. The dihedral angle between the mean plane through the O1/C2/N3/C5 atoms and that through the aromatic ring is 8.6 (1)°. A weak C—H···O interaction contributes to the stabilization of the crystal structure (Table 1).

Experimental

To a solution of 2-methoxy benzyl chloride (15.8 g, 0.1 mol) in dichloromethane (50 ml), 2-amino-2-methyl-1-propanol (8.3 g, 0.11 mol) in dichloromethane (50 ml) was added at 298–303 K over 30 min. After stirring for 1 h, dichloromethane was distilled off under reduced pressure. The obtained product was recrystallized using ethyl acetate as the solvent to yield 10 g of (I) (86.5%).

Refinement

The H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.97 Å, and with U_iso = 1.2–1.5 times U_eq(C).

Figures

Fig. 1.

The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids.

Crystal data

C12H15NO2	F000 = 440
Mr = 205.25	Dx = 1.266 Mg m−3
Monoclinic, P21/n	Melting point: 410(1) K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 8.1495 (2) Å	Cell parameters from 14583 reflections
b = 10.9369 (3) Å	θ = 4.6–32.5º
c = 12.0864 (3) Å	µ = 0.09 mm−1
β = 91.305 (3)º	T = 200 (2) K
V = 1076.99 (5) Å3	Prism, colourless
Z = 4	0.39 × 0.31 × 0.24 mm

Data collection

Oxford Diffraction Gemini diffractometer	3740 independent reflections
Radiation source: fine-focus sealed tube	2596 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 10.5081 pixels mm-1	θmax = 32.6º
T = 200(2) K	θmin = 4.6º
φ and ω scans	h = −12→12
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	k = −16→16
Tmin = 0.717, Tmax = 1.000	l = −18→18
34412 measured reflections

Refinement

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.099P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3740 reflections	Δρmax = 0.43 e Å−3
139 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Special details

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 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.61501 (9)	0.49026 (7)	0.33582 (5)	0.0357 (2)
O2	0.40996 (9)	0.22987 (6)	0.11696 (6)	0.0332 (2)
N3	0.65111 (10)	0.39575 (8)	0.17107 (7)	0.0325 (2)
C2	0.56870 (11)	0.40277 (7)	0.25852 (7)	0.0230 (2)
C4	0.78858 (13)	0.48460 (9)	0.18188 (8)	0.0310 (3)
C5	0.74394 (15)	0.55882 (10)	0.28508 (10)	0.0409 (3)
C12	0.33176 (17)	0.14486 (11)	0.04469 (10)	0.0445 (4)
C14	0.79827 (15)	0.56238 (11)	0.07847 (10)	0.0442 (4)
C15	0.94665 (14)	0.41267 (10)	0.20004 (11)	0.0428 (4)
C21	0.42972 (11)	0.32650 (8)	0.29281 (7)	0.0235 (2)
C22	0.35474 (11)	0.23841 (8)	0.22165 (7)	0.0254 (2)
C23	0.22969 (13)	0.16468 (9)	0.26164 (9)	0.0333 (3)
C24	0.18045 (13)	0.17635 (10)	0.37044 (10)	0.0389 (3)
C25	0.25034 (13)	0.26249 (11)	0.44046 (9)	0.0385 (3)
C26	0.37380 (12)	0.33708 (9)	0.40107 (8)	0.0300 (3)
H5A	0.83805	0.56661	0.33518	0.0491*
H5B	0.70600	0.63992	0.26448	0.0491*
H12A	0.38149	0.14833	−0.02649	0.0668*
H12B	0.21733	0.16474	0.03700	0.0668*
H12C	0.34348	0.06393	0.07459	0.0668*
H14A	0.82155	0.51117	0.01626	0.0662*
H14B	0.88401	0.62191	0.08799	0.0662*
H14C	0.69541	0.60335	0.06566	0.0662*
H15A	0.96128	0.35762	0.13920	0.0641*
H15B	0.94063	0.36683	0.26757	0.0641*
H15C	1.03780	0.46817	0.20484	0.0641*
H23	0.17905	0.10747	0.21531	0.0399*
H24	0.09887	0.12517	0.39659	0.0466*
H25	0.21528	0.27039	0.51280	0.0463*
H26	0.42061	0.39563	0.44781	0.0360*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0389 (4)	0.0352 (4)	0.0334 (4)	−0.0092 (3)	0.0072 (3)	−0.0128 (3)
O2	0.0348 (4)	0.0360 (4)	0.0288 (3)	−0.0099 (3)	0.0026 (3)	−0.0042 (3)
N3	0.0315 (4)	0.0313 (4)	0.0352 (4)	−0.0108 (3)	0.0101 (3)	−0.0042 (3)
C2	0.0250 (4)	0.0206 (4)	0.0234 (4)	0.0013 (3)	0.0010 (3)	−0.0022 (3)
C4	0.0303 (5)	0.0276 (5)	0.0352 (5)	−0.0080 (4)	0.0051 (4)	−0.0003 (4)
C5	0.0431 (6)	0.0303 (5)	0.0496 (7)	−0.0132 (5)	0.0087 (5)	−0.0089 (4)
C12	0.0492 (7)	0.0448 (6)	0.0394 (6)	−0.0134 (5)	−0.0026 (5)	−0.0095 (5)
C14	0.0402 (6)	0.0441 (6)	0.0483 (7)	−0.0097 (5)	0.0044 (5)	0.0124 (5)
C15	0.0354 (6)	0.0412 (6)	0.0519 (7)	−0.0010 (5)	0.0043 (5)	0.0036 (5)
C21	0.0220 (4)	0.0220 (4)	0.0266 (4)	0.0038 (3)	0.0031 (3)	0.0006 (3)
C22	0.0219 (4)	0.0258 (4)	0.0284 (4)	0.0018 (3)	0.0015 (3)	0.0011 (3)
C23	0.0246 (5)	0.0310 (5)	0.0443 (6)	−0.0041 (4)	0.0024 (4)	0.0026 (4)
C24	0.0267 (5)	0.0404 (6)	0.0500 (6)	−0.0010 (4)	0.0123 (4)	0.0112 (5)
C25	0.0335 (5)	0.0466 (6)	0.0361 (5)	0.0082 (5)	0.0135 (4)	0.0088 (4)
C26	0.0300 (5)	0.0328 (5)	0.0274 (4)	0.0066 (4)	0.0058 (4)	0.0037 (3)

Geometric parameters (Å, °)

O1—C2	1.3838 (11)	C5—H5A	0.9700
O1—C5	1.4393 (14)	C5—H5B	0.9700
O2—C12	1.4171 (14)	C12—H12A	0.9600
O2—C22	1.3558 (11)	C12—H12B	0.9600
N3—C2	1.2675 (12)	C12—H12C	0.9600
N3—C4	1.4865 (13)	C14—H14A	0.9600
C2—C21	1.4737 (12)	C14—H14B	0.9600
C4—C5	1.5387 (15)	C14—H14C	0.9600
C4—C14	1.5154 (16)	C15—H15A	0.9600
C4—C15	1.5211 (15)	C15—H15B	0.9600
C21—C22	1.4203 (12)	C15—H15C	0.9600
C21—C26	1.4001 (13)	C23—H23	0.9300
C22—C23	1.3946 (14)	C24—H24	0.9300
C23—C24	1.3895 (16)	C25—H25	0.9300
C24—C25	1.3807 (16)	C26—H26	0.9300
C25—C26	1.3879 (15)
O1···C12i	3.3873 (14)	H12B···H23	2.2700
O2···N3	2.7428 (11)	H12C···C23	2.7000
O1···H26ii	2.9200	H12C···H23	2.2400
O1···H26	2.3500	H12C···C26xi	3.0700
O1···H23iii	2.7800	H14A···H15A	2.5000
O2···H5Aiv	2.7700	H14A···C24v	2.9200
O2···H25v	2.8100	H14B···H15C	2.5100
N3···O2	2.7428 (11)	H14B···C21x	3.0500
N3···C25v	3.3942 (14)	H14B···C26x	3.0700
N3···H25v	2.7000	H14C···H5B	2.4400
C12···O1vi	3.3873 (14)	H14C···H24iii	2.4600
C25···N3vii	3.3942 (14)	H14C···C12viii	3.0700
C2···H23iii	3.0400	H15A···H14A	2.5000
C2···H15B	3.0600	H15B···C2	3.0600
C5···H25ii	3.0900	H15B···C24xii	3.1000
C12···H14Cviii	3.0700	H15B···H5A	2.4800
C12···H23	2.4700	H15B···H12Ai	2.5500
C21···H14Biv	3.0500	H15C···H5A	2.5300
C23···H12B	2.7100	H15C···H14B	2.5100
C23···H12C	2.7000	H15C···C23x	2.8900
C23···H15Civ	2.8900	H23···C12	2.4700
C24···H15Bix	3.1000	H23···H12B	2.2700
C24···H14Avii	2.9200	H23···H12C	2.2400
C26···H12Ciii	3.0700	H23···O1xi	2.7800
C26···H14Biv	3.0700	H23···C2xi	3.0400
H5A···H15B	2.4800	H24···H14Cxi	2.4600
H5A···H15C	2.5300	H25···C5ii	3.0900
H5A···O2x	2.7700	H25···O2vii	2.8100
H5B···H14C	2.4400	H25···N3vii	2.7000
H12A···H15Bvi	2.5500	H26···O1	2.3500
H12B···C23	2.7100	H26···O1ii	2.9200
C2—O1—C5	105.25 (7)	H5A—C5—H5B	109.00
C12—O2—C22	117.79 (8)	O2—C12—H12A	109.00
C2—N3—C4	107.44 (8)	O2—C12—H12B	109.00
O1—C2—N3	117.61 (8)	O2—C12—H12C	109.00
O1—C2—C21	113.65 (7)	H12A—C12—H12B	109.00
N3—C2—C21	128.72 (8)	H12A—C12—H12C	109.00
N3—C4—C5	102.97 (8)	H12B—C12—H12C	109.00
N3—C4—C14	110.35 (8)	C4—C14—H14A	109.00
N3—C4—C15	107.98 (8)	C4—C14—H14B	109.00
C5—C4—C14	112.96 (9)	C4—C14—H14C	109.00
C5—C4—C15	111.78 (9)	H14A—C14—H14B	109.00
C14—C4—C15	110.46 (9)	H14A—C14—H14C	109.00
O1—C5—C4	105.01 (8)	H14B—C14—H14C	109.00
C2—C21—C22	122.44 (8)	C4—C15—H15A	109.00
C2—C21—C26	118.99 (8)	C4—C15—H15B	109.00
C22—C21—C26	118.51 (8)	C4—C15—H15C	109.00
O2—C22—C21	117.68 (8)	H15A—C15—H15B	109.00
O2—C22—C23	122.98 (8)	H15A—C15—H15C	109.00
C21—C22—C23	119.34 (8)	H15B—C15—H15C	109.00
C22—C23—C24	120.26 (9)	C22—C23—H23	120.00
C23—C24—C25	121.25 (10)	C24—C23—H23	120.00
C24—C25—C26	118.88 (10)	C23—C24—H24	119.00
C21—C26—C25	121.73 (9)	C25—C24—H24	119.00
O1—C5—H5A	111.00	C24—C25—H25	121.00
O1—C5—H5B	111.00	C26—C25—H25	121.00
C4—C5—H5A	111.00	C21—C26—H26	119.00
C4—C5—H5B	111.00	C25—C26—H26	119.00
C5—O1—C2—N3	5.16 (11)	N3—C4—C5—O1	12.97 (10)
C5—O1—C2—C21	−176.76 (8)	C14—C4—C5—O1	132.00 (9)
C2—O1—C5—C4	−11.14 (10)	C15—C4—C5—O1	−102.69 (10)
C12—O2—C22—C21	−177.98 (9)	C2—C21—C22—O2	−3.21 (13)
C12—O2—C22—C23	2.38 (13)	C2—C21—C22—C23	176.46 (8)
C4—N3—C2—O1	3.72 (11)	C26—C21—C22—O2	179.69 (8)
C4—N3—C2—C21	−174.03 (9)	C26—C21—C22—C23	−0.65 (13)
C2—N3—C4—C5	−10.28 (10)	C2—C21—C26—C25	−175.91 (9)
C2—N3—C4—C14	−131.11 (9)	C22—C21—C26—C25	1.29 (14)
C2—N3—C4—C15	108.08 (9)	O2—C22—C23—C24	178.86 (9)
O1—C2—C21—C22	174.63 (8)	C21—C22—C23—C24	−0.79 (14)
O1—C2—C21—C26	−8.28 (12)	C22—C23—C24—C25	1.65 (16)
N3—C2—C21—C22	−7.55 (15)	C23—C24—C25—C26	−1.01 (16)
N3—C2—C21—C26	169.54 (9)	C24—C25—C26—C21	−0.48 (16)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) x+1/2, −y+1/2, z−1/2; (vi) x−1/2, −y+1/2, z−1/2; (vii) x−1/2, −y+1/2, z+1/2; (viii) −x+1, −y+1, −z; (ix) x−1, y, z; (x) −x+3/2, y+1/2, −z+1/2; (xi) −x+1/2, y−1/2, −z+1/2; (xii) x+1, y, z.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1	0.93	2.35	2.7136 (12)	103