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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o61.
Published online 2007 December 6. doi:  10.1107/S1600536807061685
PMCID: PMC2915019

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 [triangle]); Rybakov et al. (2006 [triangle]).

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Object name is e-64-00o61-scheme1.jpg

Experimental

Crystal data

  • C12H15NO2
  • M r = 205.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o61-efi1.jpg
  • a = 8.1495 (2) Å
  • b = 10.9369 (3) Å
  • c = 12.0864 (3) Å
  • β = 91.305 (3)°
  • V = 1076.99 (5) Å3
  • 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 [triangle]) 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
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.20 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061685/tk2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061685/tk2221Isup2.hkl

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

Acknowledgments

RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

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 Uiso = 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids.

Crystal data

C12H15NO2F000 = 440
Mr = 205.25Dx = 1.266 Mg m3
Monoclinic, P21/nMelting point: 410(1) K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 8.1495 (2) ÅCell parameters from 14583 reflections
b = 10.9369 (3) Åθ = 4.6–32.5º
c = 12.0864 (3) ŵ = 0.09 mm1
β = 91.305 (3)ºT = 200 (2) K
V = 1076.99 (5) Å3Prism, colourless
Z = 40.39 × 0.31 × 0.24 mm

Data collection

Oxford Diffraction Gemini diffractometer3740 independent reflections
Radiation source: fine-focus sealed tube2596 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
Detector resolution: 10.5081 pixels mm-1θmax = 32.6º
T = 200(2) Kθmin = 4.6º
[var phi] and ω scansh = −12→12
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −16→16
Tmin = 0.717, Tmax = 1.000l = −18→18
34412 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.43 e Å3
139 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction 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 (Å2)

xyzUiso*/Ueq
O10.61501 (9)0.49026 (7)0.33582 (5)0.0357 (2)
O20.40996 (9)0.22987 (6)0.11696 (6)0.0332 (2)
N30.65111 (10)0.39575 (8)0.17107 (7)0.0325 (2)
C20.56870 (11)0.40277 (7)0.25852 (7)0.0230 (2)
C40.78858 (13)0.48460 (9)0.18188 (8)0.0310 (3)
C50.74394 (15)0.55882 (10)0.28508 (10)0.0409 (3)
C120.33176 (17)0.14486 (11)0.04469 (10)0.0445 (4)
C140.79827 (15)0.56238 (11)0.07847 (10)0.0442 (4)
C150.94665 (14)0.41267 (10)0.20004 (11)0.0428 (4)
C210.42972 (11)0.32650 (8)0.29281 (7)0.0235 (2)
C220.35474 (11)0.23841 (8)0.22165 (7)0.0254 (2)
C230.22969 (13)0.16468 (9)0.26164 (9)0.0333 (3)
C240.18045 (13)0.17635 (10)0.37044 (10)0.0389 (3)
C250.25034 (13)0.26249 (11)0.44046 (9)0.0385 (3)
C260.37380 (12)0.33708 (9)0.40107 (8)0.0300 (3)
H5A0.838050.566610.335180.0491*
H5B0.706000.639920.264480.0491*
H12A0.381490.14833−0.026490.0668*
H12B0.217330.164740.037000.0668*
H12C0.343480.063930.074590.0668*
H14A0.821550.511170.016260.0662*
H14B0.884010.621910.087990.0662*
H14C0.695410.603350.065660.0662*
H15A0.961280.357620.139200.0641*
H15B0.940630.366830.267570.0641*
H15C1.037800.468170.204840.0641*
H230.179050.107470.215310.0399*
H240.098870.125170.396590.0466*
H250.215280.270390.512800.0463*
H260.420610.395630.447810.0360*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0389 (4)0.0352 (4)0.0334 (4)−0.0092 (3)0.0072 (3)−0.0128 (3)
O20.0348 (4)0.0360 (4)0.0288 (3)−0.0099 (3)0.0026 (3)−0.0042 (3)
N30.0315 (4)0.0313 (4)0.0352 (4)−0.0108 (3)0.0101 (3)−0.0042 (3)
C20.0250 (4)0.0206 (4)0.0234 (4)0.0013 (3)0.0010 (3)−0.0022 (3)
C40.0303 (5)0.0276 (5)0.0352 (5)−0.0080 (4)0.0051 (4)−0.0003 (4)
C50.0431 (6)0.0303 (5)0.0496 (7)−0.0132 (5)0.0087 (5)−0.0089 (4)
C120.0492 (7)0.0448 (6)0.0394 (6)−0.0134 (5)−0.0026 (5)−0.0095 (5)
C140.0402 (6)0.0441 (6)0.0483 (7)−0.0097 (5)0.0044 (5)0.0124 (5)
C150.0354 (6)0.0412 (6)0.0519 (7)−0.0010 (5)0.0043 (5)0.0036 (5)
C210.0220 (4)0.0220 (4)0.0266 (4)0.0038 (3)0.0031 (3)0.0006 (3)
C220.0219 (4)0.0258 (4)0.0284 (4)0.0018 (3)0.0015 (3)0.0011 (3)
C230.0246 (5)0.0310 (5)0.0443 (6)−0.0041 (4)0.0024 (4)0.0026 (4)
C240.0267 (5)0.0404 (6)0.0500 (6)−0.0010 (4)0.0123 (4)0.0112 (5)
C250.0335 (5)0.0466 (6)0.0361 (5)0.0082 (5)0.0135 (4)0.0088 (4)
C260.0300 (5)0.0328 (5)0.0274 (4)0.0066 (4)0.0058 (4)0.0037 (3)

Geometric parameters (Å, °)

O1—C21.3838 (11)C5—H5A0.9700
O1—C51.4393 (14)C5—H5B0.9700
O2—C121.4171 (14)C12—H12A0.9600
O2—C221.3558 (11)C12—H12B0.9600
N3—C21.2675 (12)C12—H12C0.9600
N3—C41.4865 (13)C14—H14A0.9600
C2—C211.4737 (12)C14—H14B0.9600
C4—C51.5387 (15)C14—H14C0.9600
C4—C141.5154 (16)C15—H15A0.9600
C4—C151.5211 (15)C15—H15B0.9600
C21—C221.4203 (12)C15—H15C0.9600
C21—C261.4001 (13)C23—H230.9300
C22—C231.3946 (14)C24—H240.9300
C23—C241.3895 (16)C25—H250.9300
C24—C251.3807 (16)C26—H260.9300
C25—C261.3879 (15)
O1···C12i3.3873 (14)H12B···H232.2700
O2···N32.7428 (11)H12C···C232.7000
O1···H26ii2.9200H12C···H232.2400
O1···H262.3500H12C···C26xi3.0700
O1···H23iii2.7800H14A···H15A2.5000
O2···H5Aiv2.7700H14A···C24v2.9200
O2···H25v2.8100H14B···H15C2.5100
N3···O22.7428 (11)H14B···C21x3.0500
N3···C25v3.3942 (14)H14B···C26x3.0700
N3···H25v2.7000H14C···H5B2.4400
C12···O1vi3.3873 (14)H14C···H24iii2.4600
C25···N3vii3.3942 (14)H14C···C12viii3.0700
C2···H23iii3.0400H15A···H14A2.5000
C2···H15B3.0600H15B···C23.0600
C5···H25ii3.0900H15B···C24xii3.1000
C12···H14Cviii3.0700H15B···H5A2.4800
C12···H232.4700H15B···H12Ai2.5500
C21···H14Biv3.0500H15C···H5A2.5300
C23···H12B2.7100H15C···H14B2.5100
C23···H12C2.7000H15C···C23x2.8900
C23···H15Civ2.8900H23···C122.4700
C24···H15Bix3.1000H23···H12B2.2700
C24···H14Avii2.9200H23···H12C2.2400
C26···H12Ciii3.0700H23···O1xi2.7800
C26···H14Biv3.0700H23···C2xi3.0400
H5A···H15B2.4800H24···H14Cxi2.4600
H5A···H15C2.5300H25···C5ii3.0900
H5A···O2x2.7700H25···O2vii2.8100
H5B···H14C2.4400H25···N3vii2.7000
H12A···H15Bvi2.5500H26···O12.3500
H12B···C232.7100H26···O1ii2.9200
C2—O1—C5105.25 (7)H5A—C5—H5B109.00
C12—O2—C22117.79 (8)O2—C12—H12A109.00
C2—N3—C4107.44 (8)O2—C12—H12B109.00
O1—C2—N3117.61 (8)O2—C12—H12C109.00
O1—C2—C21113.65 (7)H12A—C12—H12B109.00
N3—C2—C21128.72 (8)H12A—C12—H12C109.00
N3—C4—C5102.97 (8)H12B—C12—H12C109.00
N3—C4—C14110.35 (8)C4—C14—H14A109.00
N3—C4—C15107.98 (8)C4—C14—H14B109.00
C5—C4—C14112.96 (9)C4—C14—H14C109.00
C5—C4—C15111.78 (9)H14A—C14—H14B109.00
C14—C4—C15110.46 (9)H14A—C14—H14C109.00
O1—C5—C4105.01 (8)H14B—C14—H14C109.00
C2—C21—C22122.44 (8)C4—C15—H15A109.00
C2—C21—C26118.99 (8)C4—C15—H15B109.00
C22—C21—C26118.51 (8)C4—C15—H15C109.00
O2—C22—C21117.68 (8)H15A—C15—H15B109.00
O2—C22—C23122.98 (8)H15A—C15—H15C109.00
C21—C22—C23119.34 (8)H15B—C15—H15C109.00
C22—C23—C24120.26 (9)C22—C23—H23120.00
C23—C24—C25121.25 (10)C24—C23—H23120.00
C24—C25—C26118.88 (10)C23—C24—H24119.00
C21—C26—C25121.73 (9)C25—C24—H24119.00
O1—C5—H5A111.00C24—C25—H25121.00
O1—C5—H5B111.00C26—C25—H25121.00
C4—C5—H5A111.00C21—C26—H26119.00
C4—C5—H5B111.00C25—C26—H26119.00
C5—O1—C2—N35.16 (11)N3—C4—C5—O112.97 (10)
C5—O1—C2—C21−176.76 (8)C14—C4—C5—O1132.00 (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—C232.38 (13)C2—C21—C22—C23176.46 (8)
C4—N3—C2—O13.72 (11)C26—C21—C22—O2179.69 (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—C251.29 (14)
C2—N3—C4—C15108.08 (9)O2—C22—C23—C24178.86 (9)
O1—C2—C21—C22174.63 (8)C21—C22—C23—C24−0.79 (14)
O1—C2—C21—C26−8.28 (12)C22—C23—C24—C251.65 (16)
N3—C2—C21—C22−7.55 (15)C23—C24—C25—C26−1.01 (16)
N3—C2—C21—C26169.54 (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···AD—HH···AD···AD—H···A
C26—H26···O10.932.352.7136 (12)103

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2221).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Rybakov, V. B., Alifanov, V. L. & Babaev, E. V. (2006). Acta Cryst. E62, o4746–o4747.
  • Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Swaleh, S. & Ziemer, B. (2001). Acta Cryst. E57, o35–o36.

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