PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o752.
Published online 2009 March 14. doi:  10.1107/S1600536809008502
PMCID: PMC2968912

1-(2-Eth­oxy-2-methyl-2H-chromen-3-yl)ethanone

Abstract

The Csp 3 atom of the chromenyl fused-ring system in the title compound, C14H16O3, deviates by 0.407 (2) Å from the plane of the other atoms (r.m.s. deviation = 0.041 Å). The eth­oxy substituent occupies a pseudo-axial position.

Related literature

For the synthesis, see: Zonouzi et al. (2008b [triangle]). For related crystal structures, see: Bardajee et al. (2007 [triangle]); Zhan & Lin (2006 [triangle]); Zonouzi et al. (2008a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o752-scheme1.jpg

Experimental

Crystal data

  • C14H16O3
  • M r = 232.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o752-efi1.jpg
  • a = 20.0084 (5) Å
  • b = 7.2637 (2) Å
  • c = 19.1056 (5) Å
  • β = 123.294 (1)°
  • V = 2320.96 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 123 K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 7793 measured reflections
  • 2655 independent reflections
  • 2123 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.140
  • S = 1.03
  • 2655 reflections
  • 157 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008502/tk2390sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008502/tk2390Isup2.hkl

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

Acknowledgments

We thank the Research Council of Tehran University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The compound was synthesized by using a reported method (Zonouzi et al., 2008b). Crystals were obtained by recrystallization from ethanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C).

Figures

Fig. 1.
Thermal ellisoid plot (Barbour, 2001) of C14H16O3; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H16O3F(000) = 992
Mr = 232.27Dx = 1.329 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2233 reflections
a = 20.0084 (5) Åθ = 2.4–28.1°
b = 7.2637 (2) ŵ = 0.09 mm1
c = 19.1056 (5) ÅT = 123 K
β = 123.294 (1)°Irregular block, colorless
V = 2320.96 (11) Å30.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer2123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
graphiteθmax = 27.5°, θmin = 2.4°
ω scansh = −21→25
7793 measured reflectionsk = −9→9
2655 independent reflectionsl = −24→23

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0739P)2 + 1.4605P] where P = (Fo2 + 2Fc2)/3
2655 reflections(Δ/σ)max < 0.001
157 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.43 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.13572 (6)0.55707 (15)0.32959 (6)0.0208 (3)
O20.17621 (6)0.25748 (14)0.32719 (6)0.0211 (3)
O30.36134 (7)0.35871 (19)0.38669 (7)0.0350 (3)
C10.19962 (9)0.4438 (2)0.33800 (9)0.0193 (3)
C20.27375 (9)0.4496 (2)0.42713 (9)0.0189 (3)
C30.26440 (9)0.4851 (2)0.49036 (9)0.0198 (3)
H30.30980.47920.54630.024*
C40.18788 (9)0.5318 (2)0.47624 (9)0.0190 (3)
C50.17449 (9)0.5519 (2)0.54044 (9)0.0223 (3)
H50.21690.53030.59690.027*
C60.10015 (10)0.6026 (2)0.52253 (10)0.0244 (3)
H60.09170.61640.56660.029*
C70.03757 (10)0.6336 (2)0.43999 (10)0.0239 (3)
H7−0.01350.66860.42800.029*
C80.04917 (9)0.6137 (2)0.37524 (9)0.0222 (3)
H80.00630.63400.31890.027*
C90.12413 (9)0.5638 (2)0.39363 (9)0.0185 (3)
C100.20936 (10)0.5212 (2)0.27015 (9)0.0250 (4)
H10A0.15660.53840.21850.037*
H10B0.24070.43520.25970.037*
H10C0.23710.63990.28850.037*
C110.11063 (10)0.2021 (2)0.24546 (9)0.0282 (4)
H11A0.12500.21670.20370.034*
H11B0.06280.27810.22780.034*
C120.09445 (12)0.0053 (3)0.25244 (12)0.0409 (5)
H12A0.0504−0.03900.19780.061*
H12B0.0798−0.00680.29350.061*
H12C0.1425−0.06780.27060.061*
C130.35266 (9)0.3964 (2)0.44326 (9)0.0218 (3)
C140.42348 (9)0.3868 (2)0.53284 (9)0.0256 (4)
H14A0.47210.36230.53370.038*
H14B0.41520.28760.56210.038*
H14C0.42910.50430.56080.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0232 (5)0.0224 (6)0.0196 (5)0.0066 (4)0.0136 (4)0.0041 (4)
O20.0220 (6)0.0178 (6)0.0183 (5)0.0008 (4)0.0077 (4)0.0006 (4)
O30.0311 (7)0.0482 (8)0.0313 (6)0.0106 (6)0.0207 (5)0.0023 (5)
C10.0206 (7)0.0186 (7)0.0207 (7)0.0030 (6)0.0126 (6)0.0013 (5)
C20.0208 (7)0.0146 (7)0.0216 (7)0.0000 (6)0.0119 (6)0.0015 (5)
C30.0203 (7)0.0171 (7)0.0202 (7)−0.0003 (6)0.0101 (6)0.0003 (5)
C40.0222 (7)0.0155 (7)0.0212 (7)−0.0011 (6)0.0131 (6)−0.0001 (5)
C50.0258 (8)0.0206 (8)0.0211 (7)0.0000 (6)0.0132 (6)0.0001 (6)
C60.0323 (9)0.0222 (8)0.0270 (7)0.0007 (7)0.0215 (7)−0.0003 (6)
C70.0238 (8)0.0213 (8)0.0321 (8)0.0023 (6)0.0189 (7)0.0005 (6)
C80.0224 (8)0.0199 (7)0.0236 (7)0.0030 (6)0.0122 (6)0.0017 (6)
C90.0237 (7)0.0142 (7)0.0200 (7)0.0002 (6)0.0135 (6)0.0006 (5)
C100.0318 (9)0.0237 (8)0.0238 (7)0.0049 (7)0.0180 (7)0.0043 (6)
C110.0257 (8)0.0265 (9)0.0207 (7)−0.0003 (7)0.0054 (6)−0.0016 (6)
C120.0394 (11)0.0386 (11)0.0360 (9)−0.0071 (9)0.0151 (8)−0.0031 (8)
C130.0229 (8)0.0176 (7)0.0264 (7)0.0003 (6)0.0145 (6)0.0007 (6)
C140.0201 (7)0.0249 (8)0.0299 (8)−0.0002 (6)0.0125 (6)−0.0008 (6)

Geometric parameters (Å, °)

O1—C91.3654 (17)C7—C81.386 (2)
O1—C11.4531 (18)C7—H70.9500
O2—C11.4101 (18)C8—C91.388 (2)
O2—C111.4397 (17)C8—H80.9500
O3—C131.2164 (18)C10—H10A0.9800
C1—C101.520 (2)C10—H10B0.9800
C1—C21.5259 (19)C10—H10C0.9800
C2—C31.345 (2)C11—C121.488 (3)
C2—C131.484 (2)C11—H11A0.9900
C3—C41.442 (2)C11—H11B0.9900
C3—H30.9500C12—H12A0.9800
C4—C51.400 (2)C12—H12B0.9800
C4—C91.4006 (19)C12—H12C0.9800
C5—C61.381 (2)C13—C141.510 (2)
C5—H50.9500C14—H14A0.9800
C6—C71.392 (2)C14—H14B0.9800
C6—H60.9500C14—H14C0.9800
C9—O1—C1119.55 (11)O1—C9—C4120.41 (13)
C1—O2—C11117.31 (11)C8—C9—C4121.18 (13)
O2—C1—O1109.01 (12)C1—C10—H10A109.5
O2—C1—C10114.69 (12)C1—C10—H10B109.5
O1—C1—C10102.32 (11)H10A—C10—H10B109.5
O2—C1—C2103.36 (11)C1—C10—H10C109.5
O1—C1—C2111.41 (11)H10A—C10—H10C109.5
C10—C1—C2116.12 (13)H10B—C10—H10C109.5
C3—C2—C13121.33 (13)O2—C11—C12106.55 (13)
C3—C2—C1118.58 (13)O2—C11—H11A110.4
C13—C2—C1119.74 (13)C12—C11—H11A110.4
C2—C3—C4122.28 (13)O2—C11—H11B110.4
C2—C3—H3118.9C12—C11—H11B110.4
C4—C3—H3118.9H11A—C11—H11B108.6
C5—C4—C9118.45 (14)C11—C12—H12A109.5
C5—C4—C3123.72 (13)C11—C12—H12B109.5
C9—C4—C3117.81 (13)H12A—C12—H12B109.5
C6—C5—C4120.60 (14)C11—C12—H12C109.5
C6—C5—H5119.7H12A—C12—H12C109.5
C4—C5—H5119.7H12B—C12—H12C109.5
C5—C6—C7120.05 (14)O3—C13—C2121.91 (13)
C5—C6—H6120.0O3—C13—C14119.59 (14)
C7—C6—H6120.0C2—C13—C14118.49 (13)
C8—C7—C6120.47 (14)C13—C14—H14A109.5
C8—C7—H7119.8C13—C14—H14B109.5
C6—C7—H7119.8H14A—C14—H14B109.5
C7—C8—C9119.25 (14)C13—C14—H14C109.5
C7—C8—H8120.4H14A—C14—H14C109.5
C9—C8—H8120.4H14B—C14—H14C109.5
O1—C9—C8118.29 (13)
C11—O2—C1—O166.57 (15)C3—C4—C5—C6177.92 (15)
C11—O2—C1—C10−47.43 (18)C4—C5—C6—C70.3 (2)
C11—O2—C1—C2−174.83 (12)C5—C6—C7—C80.1 (2)
C9—O1—C1—O275.85 (15)C6—C7—C8—C9−0.5 (2)
C9—O1—C1—C10−162.31 (12)C1—O1—C9—C8−157.01 (13)
C9—O1—C1—C2−37.58 (17)C1—O1—C9—C426.77 (19)
O2—C1—C2—C3−90.42 (15)C7—C8—C9—O1−175.65 (13)
O1—C1—C2—C326.51 (19)C7—C8—C9—C40.5 (2)
C10—C1—C2—C3143.09 (15)C5—C4—C9—O1175.92 (13)
O2—C1—C2—C1382.91 (16)C3—C4—C9—O1−2.3 (2)
O1—C1—C2—C13−160.17 (13)C5—C4—C9—C8−0.2 (2)
C10—C1—C2—C13−43.59 (19)C3—C4—C9—C8−178.45 (14)
C13—C2—C3—C4−178.17 (14)C1—O2—C11—C12−176.06 (14)
C1—C2—C3—C4−5.0 (2)C3—C2—C13—O3177.78 (15)
C2—C3—C4—C5173.50 (14)C1—C2—C13—O34.6 (2)
C2—C3—C4—C9−8.3 (2)C3—C2—C13—C14−1.4 (2)
C9—C4—C5—C6−0.2 (2)C1—C2—C13—C14−174.50 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2390).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bardajee, G. R., Winnik, M. A. & Lough, A. J. (2007). Acta Cryst. E63, o1513–o1514.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Zhan, Y. & Lin, S.-K. (2006). Acta Cryst. E62, o2097–o2098.
  • Zonouzi, A., Rahmani, H. & Jahangiri, A. (2008a). Z. Kristallogr. New Cryst. Struct.223, 155–156.
  • Zonouzi, A., Sadeghi Googheri, M. & Miraliaaghi, P. S. (2008b). Org. Prep. Proced. Int.40, 383–389.

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