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

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

doi:10.1107/S1600536809008502

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o752

doi:10.1107/S1600536809008502

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

Afsaneh Zonouzi,^a Mojtaba Biniaz,^a Hossein Rahmani ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iran, ^bInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 March 2009; accepted 9 March 2009; online 14 March 2009)

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

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, C 2/c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 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 ).

Supporting information

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

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

checkCIF report

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.

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

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

C₁₄H₁₆O₃	F(000) = 992
M_r = 232.27	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0739P)² + 1.4605P] where P = (F_o² + 2F_c²)/3
2655 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₄H₁₆O₃	V = 2320.96 (11) Å³
M_r = 232.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.0084 (5) Å	µ = 0.09 mm⁻¹
b = 7.2637 (2) Å	T = 123 K
c = 19.1056 (5) Å	0.25 × 0.20 × 0.15 mm
β = 123.294 (1)°

Data collection top

Bruker SMART APEX diffractometer	2123 reflections with I > 2σ(I)
7793 measured reflections	R_int = 0.035
2655 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
2655 reflections	Δρ_min = −0.43 e Å⁻³
157 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆O₃
M_r	232.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	20.0084 (5), 7.2637 (2), 19.1056 (5)
β (°)	123.294 (1)
V (Å³)	2320.96 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7793, 2655, 2123
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.140, 1.03
No. of reflections	2655
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

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

References

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