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

Experimental

Crystal data

• C₁₄H₁₆O₃

• M _r = 232.27

• Monoclinic,

• a = 20.0084 (5) Å

• b = 7.2637 (2) Å

• c = 19.1056 (5) Å

• β = 123.294 (1)°

• V = 2320.96 (11) ų

• 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

• Δρ_max = 0.36 e Å⁻³

• Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶).

Supplementary Material

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

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 1.5U_eq(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

C14H16O3	F(000) = 992
Mr = 232.27	Dx = 1.329 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2233 reflections
a = 20.0084 (5) Å	θ = 2.4–28.1°
b = 7.2637 (2) Å	µ = 0.09 mm−1
c = 19.1056 (5) Å	T = 123 K
β = 123.294 (1)°	Irregular block, colorless
V = 2320.96 (11) Å3	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer	2123 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.5°, θmin = 2.4°
ω scans	h = −21→25
7793 measured reflections	k = −9→9
2655 independent reflections	l = −24→23

Refinement

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-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 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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

	x	y	z	Uiso*/Ueq
O1	0.13572 (6)	0.55707 (15)	0.32959 (6)	0.0208 (3)
O2	0.17621 (6)	0.25748 (14)	0.32719 (6)	0.0211 (3)
O3	0.36134 (7)	0.35871 (19)	0.38669 (7)	0.0350 (3)
C1	0.19962 (9)	0.4438 (2)	0.33800 (9)	0.0193 (3)
C2	0.27375 (9)	0.4496 (2)	0.42713 (9)	0.0189 (3)
C3	0.26440 (9)	0.4851 (2)	0.49036 (9)	0.0198 (3)
H3	0.3098	0.4792	0.5463	0.024*
C4	0.18788 (9)	0.5318 (2)	0.47624 (9)	0.0190 (3)
C5	0.17449 (9)	0.5519 (2)	0.54044 (9)	0.0223 (3)
H5	0.2169	0.5303	0.5969	0.027*
C6	0.10015 (10)	0.6026 (2)	0.52253 (10)	0.0244 (3)
H6	0.0917	0.6164	0.5666	0.029*
C7	0.03757 (10)	0.6336 (2)	0.43999 (10)	0.0239 (3)
H7	−0.0135	0.6686	0.4280	0.029*
C8	0.04917 (9)	0.6137 (2)	0.37524 (9)	0.0222 (3)
H8	0.0063	0.6340	0.3189	0.027*
C9	0.12413 (9)	0.5638 (2)	0.39363 (9)	0.0185 (3)
C10	0.20936 (10)	0.5212 (2)	0.27015 (9)	0.0250 (4)
H10A	0.1566	0.5384	0.2185	0.037*
H10B	0.2407	0.4352	0.2597	0.037*
H10C	0.2371	0.6399	0.2885	0.037*
C11	0.11063 (10)	0.2021 (2)	0.24546 (9)	0.0282 (4)
H11A	0.1250	0.2167	0.2037	0.034*
H11B	0.0628	0.2781	0.2278	0.034*
C12	0.09445 (12)	0.0053 (3)	0.25244 (12)	0.0409 (5)
H12A	0.0504	−0.0390	0.1978	0.061*
H12B	0.0798	−0.0068	0.2935	0.061*
H12C	0.1425	−0.0678	0.2706	0.061*
C13	0.35266 (9)	0.3964 (2)	0.44326 (9)	0.0218 (3)
C14	0.42348 (9)	0.3868 (2)	0.53284 (9)	0.0256 (4)
H14A	0.4721	0.3623	0.5337	0.038*
H14B	0.4152	0.2876	0.5621	0.038*
H14C	0.4291	0.5043	0.5608	0.038*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0232 (5)	0.0224 (6)	0.0196 (5)	0.0066 (4)	0.0136 (4)	0.0041 (4)
O2	0.0220 (6)	0.0178 (6)	0.0183 (5)	0.0008 (4)	0.0077 (4)	0.0006 (4)
O3	0.0311 (7)	0.0482 (8)	0.0313 (6)	0.0106 (6)	0.0207 (5)	0.0023 (5)
C1	0.0206 (7)	0.0186 (7)	0.0207 (7)	0.0030 (6)	0.0126 (6)	0.0013 (5)
C2	0.0208 (7)	0.0146 (7)	0.0216 (7)	0.0000 (6)	0.0119 (6)	0.0015 (5)
C3	0.0203 (7)	0.0171 (7)	0.0202 (7)	−0.0003 (6)	0.0101 (6)	0.0003 (5)
C4	0.0222 (7)	0.0155 (7)	0.0212 (7)	−0.0011 (6)	0.0131 (6)	−0.0001 (5)
C5	0.0258 (8)	0.0206 (8)	0.0211 (7)	0.0000 (6)	0.0132 (6)	0.0001 (6)
C6	0.0323 (9)	0.0222 (8)	0.0270 (7)	0.0007 (7)	0.0215 (7)	−0.0003 (6)
C7	0.0238 (8)	0.0213 (8)	0.0321 (8)	0.0023 (6)	0.0189 (7)	0.0005 (6)
C8	0.0224 (8)	0.0199 (7)	0.0236 (7)	0.0030 (6)	0.0122 (6)	0.0017 (6)
C9	0.0237 (7)	0.0142 (7)	0.0200 (7)	0.0002 (6)	0.0135 (6)	0.0006 (5)
C10	0.0318 (9)	0.0237 (8)	0.0238 (7)	0.0049 (7)	0.0180 (7)	0.0043 (6)
C11	0.0257 (8)	0.0265 (9)	0.0207 (7)	−0.0003 (7)	0.0054 (6)	−0.0016 (6)
C12	0.0394 (11)	0.0386 (11)	0.0360 (9)	−0.0071 (9)	0.0151 (8)	−0.0031 (8)
C13	0.0229 (8)	0.0176 (7)	0.0264 (7)	0.0003 (6)	0.0145 (6)	0.0007 (6)
C14	0.0201 (7)	0.0249 (8)	0.0299 (8)	−0.0002 (6)	0.0125 (6)	−0.0008 (6)

Geometric parameters (Å, °)

O1—C9	1.3654 (17)	C7—C8	1.386 (2)
O1—C1	1.4531 (18)	C7—H7	0.9500
O2—C1	1.4101 (18)	C8—C9	1.388 (2)
O2—C11	1.4397 (17)	C8—H8	0.9500
O3—C13	1.2164 (18)	C10—H10A	0.9800
C1—C10	1.520 (2)	C10—H10B	0.9800
C1—C2	1.5259 (19)	C10—H10C	0.9800
C2—C3	1.345 (2)	C11—C12	1.488 (3)
C2—C13	1.484 (2)	C11—H11A	0.9900
C3—C4	1.442 (2)	C11—H11B	0.9900
C3—H3	0.9500	C12—H12A	0.9800
C4—C5	1.400 (2)	C12—H12B	0.9800
C4—C9	1.4006 (19)	C12—H12C	0.9800
C5—C6	1.381 (2)	C13—C14	1.510 (2)
C5—H5	0.9500	C14—H14A	0.9800
C6—C7	1.392 (2)	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C9—O1—C1	119.55 (11)	O1—C9—C4	120.41 (13)
C1—O2—C11	117.31 (11)	C8—C9—C4	121.18 (13)
O2—C1—O1	109.01 (12)	C1—C10—H10A	109.5
O2—C1—C10	114.69 (12)	C1—C10—H10B	109.5
O1—C1—C10	102.32 (11)	H10A—C10—H10B	109.5
O2—C1—C2	103.36 (11)	C1—C10—H10C	109.5
O1—C1—C2	111.41 (11)	H10A—C10—H10C	109.5
C10—C1—C2	116.12 (13)	H10B—C10—H10C	109.5
C3—C2—C13	121.33 (13)	O2—C11—C12	106.55 (13)
C3—C2—C1	118.58 (13)	O2—C11—H11A	110.4
C13—C2—C1	119.74 (13)	C12—C11—H11A	110.4
C2—C3—C4	122.28 (13)	O2—C11—H11B	110.4
C2—C3—H3	118.9	C12—C11—H11B	110.4
C4—C3—H3	118.9	H11A—C11—H11B	108.6
C5—C4—C9	118.45 (14)	C11—C12—H12A	109.5
C5—C4—C3	123.72 (13)	C11—C12—H12B	109.5
C9—C4—C3	117.81 (13)	H12A—C12—H12B	109.5
C6—C5—C4	120.60 (14)	C11—C12—H12C	109.5
C6—C5—H5	119.7	H12A—C12—H12C	109.5
C4—C5—H5	119.7	H12B—C12—H12C	109.5
C5—C6—C7	120.05 (14)	O3—C13—C2	121.91 (13)
C5—C6—H6	120.0	O3—C13—C14	119.59 (14)
C7—C6—H6	120.0	C2—C13—C14	118.49 (13)
C8—C7—C6	120.47 (14)	C13—C14—H14A	109.5
C8—C7—H7	119.8	C13—C14—H14B	109.5
C6—C7—H7	119.8	H14A—C14—H14B	109.5
C7—C8—C9	119.25 (14)	C13—C14—H14C	109.5
C7—C8—H8	120.4	H14A—C14—H14C	109.5
C9—C8—H8	120.4	H14B—C14—H14C	109.5
O1—C9—C8	118.29 (13)
C11—O2—C1—O1	66.57 (15)	C3—C4—C5—C6	177.92 (15)
C11—O2—C1—C10	−47.43 (18)	C4—C5—C6—C7	0.3 (2)
C11—O2—C1—C2	−174.83 (12)	C5—C6—C7—C8	0.1 (2)
C9—O1—C1—O2	75.85 (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—C4	26.77 (19)
O2—C1—C2—C3	−90.42 (15)	C7—C8—C9—O1	−175.65 (13)
O1—C1—C2—C3	26.51 (19)	C7—C8—C9—C4	0.5 (2)
C10—C1—C2—C3	143.09 (15)	C5—C4—C9—O1	175.92 (13)
O2—C1—C2—C13	82.91 (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—O3	177.78 (15)
C2—C3—C4—C5	173.50 (14)	C1—C2—C13—O3	4.6 (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)