organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cSeQuent Scientific Limited, 120 A & B Baikampady Industrial Area, New Mangalore, India, and dDepartment of Chemistry, Mangalore University, Karnataka 574 199, India
*Correspondence e-mail: athiru@vsnl.net

(Received 18 November 2007; accepted 21 November 2007; online 6 December 2007)

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[Swaleh, S. & Ziemer, B. (2001). Acta Cryst. E57, o35-o36.]); Rybakov et al. (2006[Rybakov, V. B., Alifanov, V. L. & Babaev, E. V. (2006). Acta Cryst. E62, o4746-o4747.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15NO2

  • Mr = 205.25

  • Monoclinic, P 21 /n

  • 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[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.717, Tmax = 1.000 (expected range = 0.702–0.980)

  • 34412 measured reflections

  • 3740 independent reflections

  • 2596 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990[Sheldrick, G. M. (1990). Acta Cryst. A46, 467-473.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Structure description top

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).

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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids.
2-(2-Methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole top
Crystal data top
C12H15NO2F(000) = 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 = 4.6–32.5°
c = 12.0864 (3) ŵ = 0.09 mm1
β = 91.305 (3)°T = 200 K
V = 1076.99 (5) Å3Prism, colourless
Z = 40.39 × 0.31 × 0.24 mm
Data collection top
Oxford Diffraction Gemini
diffractometer
3740 independent reflections
Radiation source: fine-focus sealed tube2596 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 10.5081 pixels mm-1θmax = 32.6°, θmin = 4.6°
φ and ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1616
Tmin = 0.717, Tmax = 1.000l = 1818
34412 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.099P)2]
where P = (Fo2 + 2Fc2)/3
3740 reflections(Δ/σ)max < 0.001
139 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C12H15NO2V = 1076.99 (5) Å3
Mr = 205.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.1495 (2) ŵ = 0.09 mm1
b = 10.9369 (3) ÅT = 200 K
c = 12.0864 (3) Å0.39 × 0.31 × 0.24 mm
β = 91.305 (3)°
Data collection top
Oxford Diffraction Gemini
diffractometer
3740 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2596 reflections with I > 2σ(I)
Tmin = 0.717, Tmax = 1.000Rint = 0.027
34412 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 1.13Δρmax = 0.43 e Å3
3740 reflectionsΔρmin = 0.20 e Å3
139 parameters
Special details top

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) top
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*
H12A0.381490.148330.026490.0668*
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) top
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, º) top
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—C21176.76 (8)C14—C4—C5—O1132.00 (9)
C2—O1—C5—C411.14 (10)C15—C4—C5—O1102.69 (10)
C12—O2—C22—C21177.98 (9)C2—C21—C22—O23.21 (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—C21174.03 (9)C26—C21—C22—C230.65 (13)
C2—N3—C4—C510.28 (10)C2—C21—C26—C25175.91 (9)
C2—N3—C4—C14131.11 (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—C240.79 (14)
O1—C2—C21—C268.28 (12)C22—C23—C24—C251.65 (16)
N3—C2—C21—C227.55 (15)C23—C24—C25—C261.01 (16)
N3—C2—C21—C26169.54 (9)C24—C25—C26—C210.48 (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, y1/2, z+1/2; (v) x+1/2, y+1/2, z1/2; (vi) x1/2, y+1/2, z1/2; (vii) x1/2, y+1/2, z+1/2; (viii) x+1, y+1, z; (ix) x1, y, z; (x) x+3/2, y+1/2, z+1/2; (xi) x+1/2, y1/2, z+1/2; (xii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···O10.932.352.7136 (12)103

Experimental details

Crystal data
Chemical formulaC12H15NO2
Mr205.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)200
a, b, c (Å)8.1495 (2), 10.9369 (3), 12.0864 (3)
β (°) 91.305 (3)
V3)1076.99 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.39 × 0.31 × 0.24
Data collection
DiffractometerOxford Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.717, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
34412, 3740, 2596
Rint0.027
(sin θ/λ)max1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.163, 1.13
No. of reflections3740
No. of parameters139
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C26—H26···O10.932.352.7136 (12)103
 

Acknowledgements

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

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.  Google Scholar
First citationRybakov, V. B., Alifanov, V. L. & Babaev, E. V. (2006). Acta Cryst. E62, o4746–o4747.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1990). Acta Cryst. A46, 467–473.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSwaleh, S. & Ziemer, B. (2001). Acta Cryst. E57, o35–o36.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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