Crystal structure of 3-acetyl-4H-chromen-4-one

Ishikawa, Y.

doi:10.1107/S2056989015012098

organic compounds

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Volume 71| Part 7| July 2015| Page o527

doi:10.1107/S2056989015012098

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Crystal structure of 3-acetyl-4H-chromen-4-one

Yoshinobu Ishikawa ^a ^*

^aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
^*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 June 2015; accepted 24 June 2015; online 30 June 2015)

In the title compound, C₁₁H₈O₃, the fused-ring system is almost planar (r.m.s. deviation = 0.020 Å), with the largest deviation from the least-squares plane [0.0462 (17) Å] being for a pyran C atom. The dihedral angle between the plane of the fused-ring system and acetyl plane is 5.149 (16)°. In the crystal, the fused rings are linked by aromatic π–π stacking interactions [centroid–centroid distance between the benzene and pyran rings = 3.643 (6) Å] and C—H⋯O hydrogen bonds, generating a three-dimensional network.

Keywords: crystal structure; chromone; hydrogen bond; π–π stacking.

CCDC reference: 1408496

1. Related literature

For a related structure, see: Chanda et al. (2014 ). For further synthetic details, see: Yokoe et al. (1994 ); Li et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₁H₈O₃
M_r = 188.18
Monoclinic, P 2₁ /n
a = 8.016 (13) Å
b = 25.93 (6) Å
c = 4.091 (8) Å
β = 94.79 (14)°
V = 847 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.42 × 0.25 × 0.20 mm

2.2. Data collection

Rigaku AFC-7R diffractometer
2377 measured reflections
1962 independent reflections
1510 reflections with F² > 2.0σ(F²)
R_int = 0.018
3 standard reflections every 150 reflections intensity decay: −0.5%

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.03
1959 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H5⋯O2ⁱ	0.95	2.40	3.292 (6)	155
C1—H1⋯O3ⁱⁱ	0.95	2.31	3.264 (5)	148
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+3.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 $[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]$ ); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla, et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1408496

Crystal structure: contains datablocks General, I. DOI: 10.1107/S2056989015012098/hb7454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015012098/hb7454Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015012098/hb7454Isup3.cml

checkCIF report

Comment top

Many derivatives of the title compound are reported because of their chemical, biological and medicinal significance (Yokoe et al. 1994, Chanda et al. 2014).

The mean deviation of the least-square plane for the non-hydrogen atoms of the fused-ring is 0.0201 Å, and the largest deviation from the plane is 0.0462 (17) Å for C2. These mean that these atoms are essentially coplanar (Fig.1). The dihedral angle between the fused-ring and acetyl plane is 5.149 (16) Å.

In the crystal, the molecules are linked by π–π stacking [centroid–centroid distance between the benzene and pyran rings = 3.643 (6) Å], and C–H···O hydrogen bonds form sheets along [0 4 1] and [0 4 1], as shown in Fig.2 and Fig.3.

The crystal structure of a 2,5,6,7-substituted 3-acetylchromone derivative is reported (Chanda et al. 2014).

Related literature top

For a related structure, see: Chanda et al. (2014). For further synthetic details, see: Yokoe et al. (1994); Li et al. (2012).

Experimental top

The title compound was synthesized from 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-enone (Li et al. 2012) according to the literature method (Yokoe et al. 1994). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution of the title compound at room temperature.

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla, et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. A view of the intermolecular interactions of the title compound. C–H···O hydrogen bonds are represented as dashed lines.
	Fig. 3. A view of the title compound down to the a-axis.

3-Acetyl-4H-chromen-4-one top

Crystal data top

C₁₁H₈O₃	F(000) = 392.00
M_r = 188.18	D_x = 1.475 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.016 (13) Å	θ = 15.2–17.5°
b = 25.93 (6) Å	µ = 0.11 mm⁻¹
c = 4.091 (8) Å	T = 100 K
β = 94.79 (14)°	Prismatic, colorless
V = 847 (3) Å³	0.42 × 0.25 × 0.20 mm
Z = 4

Data collection top

Rigaku AFC-7R diffractometer	θ_max = 27.6°
ω scans	h = −5→10
2377 measured reflections	k = 0→33
1962 independent reflections	l = −5→5
1510 reflections with F² > 2.0σ(F²)	3 standard reflections every 150 reflections
R_int = 0.018	intensity decay: −0.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0509P)² + 0.3687P] where P = (F_o² + 2F_c²)/3
1959 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₈O₃	V = 847 (3) Å³
M_r = 188.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.016 (13) Å	µ = 0.11 mm⁻¹
b = 25.93 (6) Å	T = 100 K
c = 4.091 (8) Å	0.42 × 0.25 × 0.20 mm
β = 94.79 (14)°

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.018
2377 measured reflections	3 standard reflections every 150 reflections
1962 independent reflections	intensity decay: −0.5%
1510 reflections with F² > 2.0σ(F²)

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
1959 reflections	Δρ_min = −0.20 e Å⁻³
128 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O1	−0.18103 (13)	0.09136 (4)	1.0184 (3)	0.0256 (3)
O2	0.27801 (13)	0.14078 (4)	0.7749 (3)	0.0296 (3)
O3	0.22177 (14)	0.01208 (4)	1.3956 (4)	0.0352 (3)
C1	−0.03986 (18)	0.06711 (6)	1.1256 (4)	0.0239 (4)
C2	0.11774 (18)	0.08077 (5)	1.0636 (4)	0.0212 (3)
C3	0.14176 (18)	0.12556 (6)	0.8560 (4)	0.0210 (3)
C4	−0.01216 (18)	0.19777 (6)	0.5570 (4)	0.0233 (4)
C5	−0.1584 (2)	0.22372 (6)	0.4646 (4)	0.0264 (4)
C6	−0.31159 (19)	0.20407 (6)	0.5507 (4)	0.0268 (4)
C7	−0.31830 (18)	0.15967 (6)	0.7318 (4)	0.0251 (4)
C8	−0.01438 (17)	0.15278 (5)	0.7452 (4)	0.0202 (3)
C9	−0.16842 (18)	0.13482 (5)	0.8296 (4)	0.0212 (3)
C10	0.25597 (19)	0.04850 (6)	1.2256 (4)	0.0232 (4)
C11	0.43401 (19)	0.06180 (6)	1.1822 (5)	0.0270 (4)
H1	−0.0510	0.0374	1.2581	0.0286*
H2	0.0912	0.2105	0.4924	0.0280*
H3	−0.1554	0.2549	0.3429	0.0316*
H4	−0.4124	0.2217	0.4826	0.0322*
H5	−0.4223	0.1463	0.7889	0.0301*
H6A	0.5082	0.0387	1.3165	0.0324*
H7B	0.4557	0.0976	1.2506	0.0324*
H8C	0.4550	0.0579	0.9509	0.0324*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0172 (5)	0.0250 (6)	0.0351 (6)	−0.0015 (4)	0.0041 (5)	0.0048 (5)
O2	0.0169 (6)	0.0302 (6)	0.0419 (7)	−0.0011 (5)	0.0043 (5)	0.0109 (5)
O3	0.0269 (6)	0.0319 (7)	0.0468 (8)	0.0004 (5)	0.0032 (6)	0.0164 (6)
C1	0.0211 (7)	0.0222 (7)	0.0282 (8)	−0.0004 (6)	0.0018 (6)	0.0013 (6)
C2	0.0183 (7)	0.0202 (7)	0.0250 (8)	−0.0003 (6)	0.0018 (6)	−0.0014 (6)
C3	0.0175 (7)	0.0213 (7)	0.0243 (8)	−0.0013 (6)	0.0026 (6)	−0.0023 (6)
C4	0.0207 (7)	0.0231 (7)	0.0261 (8)	−0.0014 (6)	0.0015 (6)	−0.0012 (6)
C5	0.0273 (8)	0.0234 (8)	0.0280 (8)	0.0021 (6)	−0.0001 (7)	0.0017 (7)
C6	0.0205 (8)	0.0310 (9)	0.0285 (8)	0.0056 (6)	0.0000 (6)	−0.0010 (7)
C7	0.0178 (7)	0.0293 (8)	0.0283 (8)	0.0001 (6)	0.0028 (6)	−0.0031 (7)
C8	0.0175 (7)	0.0204 (7)	0.0227 (8)	−0.0003 (6)	0.0017 (6)	−0.0036 (6)
C9	0.0192 (7)	0.0206 (7)	0.0239 (8)	−0.0007 (6)	0.0023 (6)	−0.0020 (6)
C10	0.0217 (8)	0.0224 (7)	0.0253 (8)	0.0008 (6)	0.0017 (6)	0.0001 (6)
C11	0.0193 (8)	0.0288 (8)	0.0327 (9)	0.0018 (6)	0.0011 (6)	0.0060 (7)

Geometric parameters (Å, º) top

O1—C1	1.336 (3)	C7—C9	1.392 (3)
O1—C9	1.375 (3)	C8—C9	1.390 (3)
O2—C3	1.233 (3)	C10—C11	1.493 (3)
O3—C10	1.218 (3)	C1—H1	0.950
C1—C2	1.356 (3)	C4—H2	0.950
C2—C3	1.461 (3)	C5—H3	0.950
C2—C10	1.498 (3)	C6—H4	0.950
C3—C8	1.475 (3)	C7—H5	0.950
C4—C5	1.377 (3)	C11—H6A	0.980
C4—C8	1.399 (3)	C11—H7B	0.980
C5—C6	1.401 (3)	C11—H8C	0.980
C6—C7	1.373 (4)

C1—O1—C9	118.05 (15)	O3—C10—C11	120.67 (16)
O1—C1—C2	126.32 (18)	C2—C10—C11	119.82 (17)
C1—C2—C3	119.10 (15)	O1—C1—H1	116.840
C1—C2—C10	115.94 (17)	C2—C1—H1	116.843
C3—C2—C10	124.94 (16)	C5—C4—H2	119.697
O2—C3—C2	125.01 (15)	C8—C4—H2	119.697
O2—C3—C8	120.81 (18)	C4—C5—H3	120.092
C2—C3—C8	114.17 (16)	C6—C5—H3	120.097
C5—C4—C8	120.61 (17)	C5—C6—H4	119.500
C4—C5—C6	119.81 (19)	C7—C6—H4	119.487
C5—C6—C7	121.01 (16)	C6—C7—H5	120.923
C6—C7—C9	118.14 (17)	C9—C7—H5	120.937
C3—C8—C4	121.26 (16)	C10—C11—H6A	109.476
C3—C8—C9	120.79 (17)	C10—C11—H7B	109.464
C4—C8—C9	117.95 (15)	C10—C11—H8C	109.473
O1—C9—C7	116.03 (16)	H6A—C11—H7B	109.469
O1—C9—C8	121.52 (15)	H6A—C11—H8C	109.475
C7—C9—C8	122.45 (17)	H7B—C11—H8C	109.471
O3—C10—C2	119.50 (17)

C1—O1—C9—C7	−178.13 (12)	H2—C4—C5—H3	−2.1
C1—O1—C9—C8	1.35 (19)	H2—C4—C8—C3	2.2
C9—O1—C1—C2	−0.8 (3)	H2—C4—C8—C9	−178.8
C9—O1—C1—H1	179.2	C4—C5—C6—C7	1.3 (3)
O1—C1—C2—C3	−1.2 (3)	C4—C5—C6—H4	−178.7
O1—C1—C2—C10	177.31 (13)	H3—C5—C6—C7	−178.7
H1—C1—C2—C3	178.9	H3—C5—C6—H4	1.3
H1—C1—C2—C10	−2.7	C5—C6—C7—C9	0.4 (3)
C1—C2—C3—O2	−177.82 (14)	C5—C6—C7—H5	−179.6
C1—C2—C3—C8	2.4 (2)	H4—C6—C7—C9	−179.6
C1—C2—C10—O3	1.2 (2)	H4—C6—C7—H5	0.4
C1—C2—C10—C11	−177.68 (13)	C6—C7—C9—O1	178.20 (13)
C3—C2—C10—O3	179.57 (13)	C6—C7—C9—C8	−1.3 (3)
C3—C2—C10—C11	0.7 (3)	H5—C7—C9—O1	−1.8
C10—C2—C3—O2	3.9 (3)	H5—C7—C9—C8	178.7
C10—C2—C3—C8	−175.94 (12)	C3—C8—C9—O1	0.0 (2)
O2—C3—C8—C4	−2.7 (3)	C3—C8—C9—C7	179.50 (12)
O2—C3—C8—C9	178.31 (13)	C4—C8—C9—O1	−178.94 (12)
C2—C3—C8—C4	177.09 (12)	C4—C8—C9—C7	0.5 (2)
C2—C3—C8—C9	−1.87 (19)	O3—C10—C11—H6A	−3.2
C5—C4—C8—C3	−177.81 (13)	O3—C10—C11—H7B	−123.2
C5—C4—C8—C9	1.2 (2)	O3—C10—C11—H8C	116.8
C8—C4—C5—C6	−2.0 (3)	C2—C10—C11—H6A	175.7
C8—C4—C5—H3	177.9	C2—C10—C11—H7B	55.7
H2—C4—C5—C6	178.0	C2—C10—C11—H8C	−64.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H5···O2ⁱ	0.95	2.40	3.292 (6)	155
C1—H1···O3ⁱⁱ	0.95	2.31	3.264 (5)	148

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+3.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H5···O2ⁱ	0.95	2.40	3.292 (6)	155
C1—H1···O3ⁱⁱ	0.95	2.31	3.264 (5)	148

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+3.

Acknowledgements

The University of Shizuoka is acknowledged for instrumental support.

References

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