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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2215.
Published online 2009 August 22. doi:  10.1107/S1600536809032243
PMCID: PMC2970125

4-[(2-Methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-yl­idene)meth­yl]phenyl acetate

Abstract

In the title compound, C13H11NO4, an intramolecular C—H(...)N interaction helps to establish the conformation. In the crystal, two C—H(...)O contacts stack adjacent mol­ecules into a one-dimensional double chain running in the a-axis direction.

Related literature

The title compound is an important medical inter­mediate, see: Baker (1951 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2215-scheme1.jpg

Experimental

Crystal data

  • C13H11NO4
  • M r = 245.23
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2215-efi1.jpg
  • a = 5.5802 (15) Å
  • b = 7.446 (2) Å
  • c = 15.012 (4) Å
  • α = 94.322 (4)°
  • β = 93.156 (4)°
  • γ = 108.136 (4)°
  • V = 589.1 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.14 × 0.13 × 0.08 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003 [triangle]) T min = 0.985, T max = 0.992
  • 3324 measured reflections
  • 2264 independent reflections
  • 1707 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.164
  • S = 1.04
  • 2264 reflections
  • 153 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT-Plus (Bruker, 1998 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032243/kj2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032243/kj2130Isup2.hkl

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

Acknowledgments

This work was supported by Guangdong Provincial Key Laboratory of Emergency Testing for Dangerous Chemicals, China National Analytical Center (Guangzhou), People’s Republic of China.

supplementary crystallographic information

Comment

The title compound is an important medical intermediate (Baker, 1951). Here we report the molecular and crystal structure of the title compound (Fig. 1). In the cystal structure,the five- and six-membered rings are nearly coplanar. The interplanar angle between the two rings is 1.392 (3)°. The crystal packing (Fig. 2) is stabilized by two types of intermolecular C—H···O interactions and one kind of intramolecular C—H···N interaction. Details are listed in Table 1. These interactions join the molecules into a double chain parallel to the a axis.

Experimental

The title compund is synthesized according to previous reported literature (Baker, 1951). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in dichloromethane at room temperature.

Refinement

For Methyls, H atoms were positioned theoretically with Uiso(H) = 1.5Ueq(C). The other H atoms in the title compound were placed geometrically and refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(C)], using a riding model.

Figures

Fig. 1.
A view of the title compound with the atom-labeling scheme and 30% probability displacement ellipsoids.
Fig. 2.
Perspective view along the b-axis of the crystal packing of the title compound. Dashed lines indicate C-H···O and C-H···N contacts.

Crystal data

C13H11NO4Z = 2
Mr = 245.23F(000) = 256
Triclinic, P1Dx = 1.383 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.5802 (15) ÅCell parameters from 2544 reflections
b = 7.446 (2) Åθ = 3.0–25.4°
c = 15.012 (4) ŵ = 0.10 mm1
α = 94.322 (4)°T = 293 K
β = 93.156 (4)°Block, colourless
γ = 108.136 (4)°0.14 × 0.13 × 0.08 mm
V = 589.1 (3) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer2264 independent reflections
Radiation source: fine-focus sealed tube1707 reflections with I > 2σ(I)
graphiteRint = 0.016
Detector resolution: 15 pixels mm-1θmax = 26.1°, θmin = 2.7°
[var phi] and ω scansh = −6→3
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003)k = −9→9
Tmin = 0.985, Tmax = 0.992l = −18→15
3324 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0685P)2 + 0.3541P] where P = (Fo2 + 2Fc2)/3
2264 reflections(Δ/σ)max < 0.001
153 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
N10.4700 (4)0.9795 (3)0.17606 (14)0.0516 (6)
O11.3127 (3)0.7316 (3)0.44177 (12)0.0565 (5)
O20.2844 (4)0.6674 (3)−0.02010 (13)0.0725 (6)
O30.2123 (4)0.9237 (3)0.04884 (12)0.0568 (5)
O41.0311 (4)0.7157 (3)0.54417 (13)0.0631 (6)
C11.1357 (5)0.7294 (4)0.37105 (17)0.0491 (6)
C21.1061 (5)0.5959 (4)0.29939 (17)0.0540 (7)
H21.19500.50910.30020.065*
C30.9434 (5)0.5922 (4)0.22626 (17)0.0518 (7)
H30.92290.50190.17780.062*
C40.8449 (5)0.8561 (4)0.29798 (17)0.0529 (7)
H40.75740.94390.29800.064*
C51.0078 (5)0.8603 (4)0.37083 (17)0.0552 (7)
H51.03120.95070.41950.066*
C60.8087 (5)0.7219 (3)0.22381 (16)0.0460 (6)
C70.6402 (5)0.7112 (4)0.14512 (17)0.0485 (6)
H70.63120.61400.10100.058*
C80.4950 (5)0.8196 (3)0.12586 (16)0.0456 (6)
C90.3284 (5)0.7834 (4)0.04328 (18)0.0517 (6)
C100.3096 (6)1.0311 (4)0.1294 (2)0.0614 (5)
C110.2127 (6)1.1906 (4)0.1497 (2)0.0614 (5)
H11A0.29771.26190.20460.092*
H11B0.03431.14270.15580.092*
H11C0.24301.27150.10190.092*
C121.2360 (5)0.7171 (4)0.52634 (17)0.0483 (6)
C131.4387 (6)0.6997 (4)0.5901 (2)0.0614 (5)
H13A1.45210.78170.64390.092*
H13B1.59690.73530.56320.092*
H13C1.39840.57070.60440.092*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0563 (13)0.0520 (13)0.0512 (12)0.0260 (10)−0.0003 (10)−0.0015 (10)
O10.0468 (10)0.0774 (13)0.0507 (11)0.0283 (9)0.0027 (8)0.0039 (9)
O20.0901 (16)0.0779 (14)0.0548 (12)0.0428 (12)−0.0140 (11)−0.0167 (11)
O30.0637 (12)0.0609 (12)0.0513 (11)0.0312 (10)−0.0071 (9)−0.0008 (9)
O40.0549 (12)0.0869 (15)0.0590 (12)0.0379 (11)0.0086 (9)0.0100 (10)
C10.0461 (14)0.0585 (15)0.0465 (14)0.0220 (12)0.0049 (11)0.0049 (12)
C20.0600 (16)0.0603 (16)0.0524 (15)0.0355 (14)0.0043 (13)0.0020 (13)
C30.0634 (17)0.0516 (15)0.0470 (14)0.0295 (13)0.0039 (12)−0.0020 (11)
C40.0654 (17)0.0523 (15)0.0507 (15)0.0339 (13)0.0019 (13)0.0007 (12)
C50.0665 (17)0.0570 (16)0.0468 (14)0.0299 (14)−0.0005 (13)−0.0061 (12)
C60.0512 (14)0.0463 (13)0.0450 (13)0.0219 (11)0.0058 (11)0.0030 (11)
C70.0563 (15)0.0482 (14)0.0442 (13)0.0220 (12)0.0046 (11)0.0001 (11)
C80.0502 (14)0.0469 (13)0.0429 (13)0.0206 (11)0.0040 (11)0.0026 (10)
C90.0581 (16)0.0522 (15)0.0493 (14)0.0249 (13)0.0031 (12)0.0025 (12)
C100.0603 (10)0.0662 (11)0.0616 (10)0.0281 (8)−0.0028 (8)0.0013 (8)
C110.0603 (10)0.0662 (11)0.0616 (10)0.0281 (8)−0.0028 (8)0.0013 (8)
C120.0472 (15)0.0487 (14)0.0487 (14)0.0173 (12)−0.0005 (11)−0.0029 (11)
C130.0603 (10)0.0662 (11)0.0616 (10)0.0281 (8)−0.0028 (8)0.0013 (8)

Geometric parameters (Å, °)

N1—C101.275 (3)C4—C61.400 (3)
N1—C81.409 (3)C4—H40.9300
O1—C121.363 (3)C5—H50.9300
O1—C11.405 (3)C6—C71.450 (3)
O2—C91.196 (3)C7—C81.345 (4)
O3—C101.381 (3)C7—H70.9300
O3—C91.390 (3)C8—C91.463 (4)
O4—C121.185 (3)C10—C111.469 (4)
C1—C21.374 (4)C11—H11A0.9600
C1—C51.376 (4)C11—H11B0.9600
C2—C31.379 (4)C11—H11C0.9600
C2—H20.9300C12—C131.484 (4)
C3—C61.398 (3)C13—H13A0.9600
C3—H30.9300C13—H13B0.9600
C4—C51.375 (4)C13—H13C0.9600
C10—N1—C8105.4 (2)C7—C8—N1129.4 (2)
C12—O1—C1118.8 (2)C7—C8—C9122.6 (2)
C10—O3—C9105.4 (2)N1—C8—C9108.0 (2)
C2—C1—C5121.3 (2)O2—C9—O3121.5 (2)
C2—C1—O1116.6 (2)O2—C9—C8133.5 (2)
C5—C1—O1122.0 (2)O3—C9—C8105.0 (2)
C1—C2—C3119.3 (2)N1—C10—O3116.3 (2)
C1—C2—H2120.3N1—C10—C11128.7 (3)
C3—C2—H2120.3O3—C10—C11115.1 (2)
C2—C3—C6121.1 (2)C10—C11—H11A109.5
C2—C3—H3119.5C10—C11—H11B109.5
C6—C3—H3119.5H11A—C11—H11B109.5
C5—C4—C6121.1 (2)C10—C11—H11C109.5
C5—C4—H4119.4H11A—C11—H11C109.5
C6—C4—H4119.4H11B—C11—H11C109.5
C4—C5—C1119.4 (2)O4—C12—O1123.0 (2)
C4—C5—H5120.3O4—C12—C13125.9 (3)
C1—C5—H5120.3O1—C12—C13111.1 (2)
C3—C6—C4117.8 (2)C12—C13—H13A109.5
C3—C6—C7118.6 (2)C12—C13—H13B109.5
C4—C6—C7123.6 (2)H13A—C13—H13B109.5
C8—C7—C6130.1 (2)C12—C13—H13C109.5
C8—C7—H7114.9H13A—C13—H13C109.5
C6—C7—H7114.9H13B—C13—H13C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···N10.932.453.098 (4)127
C7—H7···O2i0.932.533.417 (4)160
C13—H13B···O4ii0.962.503.382 (4)152

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2130).

References

  • Baker, L. E. (1951). J. Biol. Chem.193, 809–819. [PubMed]
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2003). SAINT-Plus Bruker AXS Inc., Madison, Wisconsion, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography