supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o752    [ doi:10.1107/S1600536809008502 ]

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

A. Zonouzi, M. Biniaz, H. Rahmani and S. W. Ng

Abstract top

The Csp3 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 top

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

Experimental top

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

Refinement top

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).

Computing details top

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

Figures top
[Figure 1] 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.
1-(2-Ethoxy-2-methyl-2H-chromen-3-yl)ethanone top
Crystal data top
C14H16O3F(000) = 992
Mr = 232.27Dx = 1.329 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		2123 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 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C14H16O3V = 2320.96 (11) Å3
Mr = 232.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 20.0084 (5) ŵ = 0.09 mm−1
b = 7.2637 (2) ÅT = 123 K
c = 19.1056 (5) Å0.25 × 0.20 × 0.15 mm
β = 123.294 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2123 reflections with I > 2σ(I)
7793 measured reflectionsRint = 0.035
2655 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.140Δρmax = 0.36 e Å−3
S = 1.03Δρmin = −0.43 e Å−3
2655 reflectionsAbsolute structure: ?
157 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

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

references
References top

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.

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.