2H-Chromen-4(3H)-one

Betz, R.; McCleland, C.; Marchand, H.

doi:10.1107/S1600536811013535

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1151

doi:10.1107/S1600536811013535

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2H-Chromen-4(3H)-one

Richard Betz,^a ^* Cedric McCleland ^a and Harold Marchand ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 5 April 2011; accepted 11 April 2011; online 16 April 2011)

In the title compound, C₉H₈O₂, a benzo-annulated heterocyclic ketone, the non-aromatic six-membered ring adopts an E₂ conformation. In the crystal, C—H⋯O contacts connect the molecules into double sheets perpendicular to the crystallographic a axis. The centroid–centroid distance for two π-systems is 3.7699 (6) Å.

Related literature

For the structure of a chromium(0) compound containing the title compound as a ligand, see: Stewart et al. (1984 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₉H₈O₂
M_r = 148.15
Monoclinic, P 2₁ /c
a = 7.5538 (4) Å
b = 8.0896 (4) Å
c = 13.0410 (6) Å
β = 115.364 (3)°
V = 720.08 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.48 × 0.41 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer
6367 measured reflections
1774 independent reflections
1578 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.05
1774 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H11⋯O2ⁱ	0.99	2.53	3.4674 (13)	157
C1—H12⋯O2ⁱⁱ	0.99	2.56	3.3934 (15)	141
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae,et al., 2006 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013535/lw2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013535/lw2060Isup2.hkl

checkCIF report

Comment top

In general, saturated, six-membered carbocycles and heterocycles adopt energetically favourable chair- or boat-conformations in solution and in the solid state although a variety of other conformations such as half-chair- or twist-forms are available. The annulation of aromatic rings can influence the conformation of such ring-systems and "freeze" one of the less common conformations. In our continued interest in effects of substituents and annulation of differently-substituted aromatic systems on the conformation of six-, seven- and eight-membered ring systems, we determined the crystal structure of the title compound to enable comparative studies. As of today, only one structural analysis of a chromium(0)-compound featuring the title compound as a ligand is apparent in the literature (Stewart et al. 1984).

The heterocyclic six-membered ring adopts an E₂ conformation with carbon atom C1 acting as the envelope-atom. The latter one is displaced by 0.337 (1) Å from the least-squares plane defined by the atoms of the heterocycle. The least-squares planes defined by the carbon atoms of the phenyl ring as well as the skeletal atoms of the heterocycle intersect at an angle of 7.73 (6)°.

In the crystal structure, C–H···O contacts whose ranges fall by about 0.2 Å below the sum of van-der-Waals radii of the atoms participating are observed. These include both H atoms of the methylene group in ortho-position to the intracyclic O atom as donor atoms and exclusively the O atom of the carbonyl group as acceptor (Fig. 2). In total, the molecules are connected to double layers perpendicular to the crystallographic a axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995) the descriptor for these contacts on the unitary level is C(5)C(5). The shortest C_g···C_g-distance for two π-systems was measured at 3.7699 (6) Å.

The packing of the title compound is shown in Figure 3.

Related literature top

For the structure of a chromium(0) compound containing the title compound as a ligand, see: Stewart et al. (1984). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975).

Experimental top

The compound was obtained commercially (Aldrich). Crystals suitable for the X-ray diffraction study were taken directly from the provided product.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae, et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. Symmetry operators: ⁱ x, -y + 1/2, z + 1/2; ⁱⁱ -x, y - 1/2, -z + 1/2; ⁱⁱⁱ -x, y + 1/2, -z + 1/2; ^iv x, -y + 1/2, z - 1/2.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

2H-Chromen-4(3H)-one top

Crystal data top

C₉H₈O₂	F(000) = 312
M_r = 148.15	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 308–311 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.5538 (4) Å	Cell parameters from 4401 reflections
b = 8.0896 (4) Å	θ = 3.0–28.3°
c = 13.0410 (6) Å	µ = 0.10 mm⁻¹
β = 115.364 (3)°	T = 200 K
V = 720.08 (6) Å³	Block, colourless
Z = 4	0.48 × 0.41 × 0.29 mm

Data collection top

Bruker APEXII CCD diffractometer	1578 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 28.3°, θ_min = 3.5°
ϕ and ω scans	h = −9→10
6367 measured reflections	k = −10→10
1774 independent reflections	l = −17→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0588P)² + 0.1339P] where P = (F_o² + 2F_c²)/3
1774 reflections	(Δ/σ)_max < 0.001
100 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₉H₈O₂	V = 720.08 (6) Å³
M_r = 148.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5538 (4) Å	µ = 0.10 mm⁻¹
b = 8.0896 (4) Å	T = 200 K
c = 13.0410 (6) Å	0.48 × 0.41 × 0.29 mm
β = 115.364 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1578 reflections with I > 2σ(I)
6367 measured reflections	R_int = 0.041
1774 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
1774 reflections	Δρ_min = −0.19 e Å⁻³
100 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.32152 (11)	0.53935 (9)	0.22765 (6)	0.0337 (2)
O2	0.15764 (13)	0.19047 (10)	0.39707 (7)	0.0434 (2)
C1	0.20014 (15)	0.40212 (13)	0.16627 (8)	0.0327 (2)
H11	0.2296	0.3735	0.1014	0.039*
H12	0.0606	0.4348	0.1357	0.039*
C2	0.23447 (15)	0.25263 (12)	0.24191 (8)	0.0307 (2)
H21	0.1432	0.1632	0.1991	0.037*
H22	0.3699	0.2120	0.2654	0.037*
C3	0.20392 (13)	0.29406 (11)	0.34541 (8)	0.0262 (2)
C4	0.23848 (12)	0.46883 (11)	0.38176 (7)	0.0232 (2)
C5	0.29805 (12)	0.58227 (11)	0.32203 (8)	0.0255 (2)
C6	0.33856 (14)	0.74544 (12)	0.35963 (9)	0.0349 (2)
H6	0.3802	0.8228	0.3197	0.042*
C7	0.31759 (15)	0.79357 (13)	0.45538 (10)	0.0400 (3)
H7	0.3450	0.9047	0.4807	0.048*
C8	0.25740 (16)	0.68291 (14)	0.51532 (9)	0.0389 (3)
H8	0.2424	0.7180	0.5807	0.047*
C9	0.21953 (14)	0.52099 (13)	0.47876 (8)	0.0310 (2)
H9	0.1801	0.4441	0.5200	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (4)	0.0338 (4)	0.0332 (4)	−0.0066 (3)	0.0217 (3)	0.0014 (3)
O2	0.0608 (5)	0.0309 (4)	0.0420 (4)	−0.0108 (3)	0.0254 (4)	0.0046 (3)
C1	0.0385 (5)	0.0353 (5)	0.0253 (4)	−0.0009 (4)	0.0146 (4)	−0.0024 (4)
C2	0.0348 (5)	0.0262 (4)	0.0318 (5)	−0.0008 (4)	0.0147 (4)	−0.0051 (4)
C3	0.0263 (4)	0.0239 (4)	0.0267 (4)	−0.0010 (3)	0.0098 (3)	0.0018 (3)
C4	0.0221 (4)	0.0233 (4)	0.0231 (4)	0.0013 (3)	0.0086 (3)	0.0007 (3)
C5	0.0234 (4)	0.0240 (4)	0.0279 (4)	−0.0001 (3)	0.0098 (3)	0.0012 (3)
C6	0.0318 (5)	0.0236 (5)	0.0446 (6)	−0.0032 (4)	0.0117 (4)	0.0013 (4)
C7	0.0329 (5)	0.0275 (5)	0.0474 (6)	0.0022 (4)	0.0057 (4)	−0.0114 (4)
C8	0.0374 (5)	0.0423 (6)	0.0314 (5)	0.0087 (4)	0.0095 (4)	−0.0107 (4)
C9	0.0313 (5)	0.0358 (5)	0.0256 (4)	0.0042 (4)	0.0121 (4)	0.0001 (4)

Geometric parameters (Å, º) top

O1—C5	1.3616 (11)	C4—C5	1.3970 (12)
O1—C1	1.4439 (12)	C4—C9	1.3977 (13)
O2—C3	1.2166 (12)	C5—C6	1.3957 (13)
C1—C2	1.5112 (14)	C6—C7	1.3803 (16)
C1—H11	0.9900	C6—H6	0.9500
C1—H12	0.9900	C7—C8	1.3870 (18)
C2—C3	1.5013 (13)	C7—H7	0.9500
C2—H21	0.9900	C8—C9	1.3813 (15)
C2—H22	0.9900	C8—H8	0.9500
C3—C4	1.4785 (12)	C9—H9	0.9500

C5—O1—C1	113.55 (7)	C5—C4—C3	120.27 (8)
O1—C1—C2	111.27 (8)	C9—C4—C3	120.43 (9)
O1—C1—H11	109.4	O1—C5—C6	117.70 (9)
C2—C1—H11	109.4	O1—C5—C4	122.30 (8)
O1—C1—H12	109.4	C6—C5—C4	119.99 (9)
C2—C1—H12	109.4	C7—C6—C5	119.45 (10)
H11—C1—H12	108.0	C7—C6—H6	120.3
C3—C2—C1	111.02 (8)	C5—C6—H6	120.3
C3—C2—H21	109.4	C6—C7—C8	121.35 (9)
C1—C2—H21	109.4	C6—C7—H7	119.3
C3—C2—H22	109.4	C8—C7—H7	119.3
C1—C2—H22	109.4	C9—C8—C7	119.13 (10)
H21—C2—H22	108.0	C9—C8—H8	120.4
O2—C3—C4	122.29 (9)	C7—C8—H8	120.4
O2—C3—C2	122.37 (9)	C8—C9—C4	120.82 (10)
C4—C3—C2	115.33 (8)	C8—C9—H9	119.6
C5—C4—C9	119.25 (9)	C4—C9—H9	119.6

C5—O1—C1—C2	−55.93 (11)	C3—C4—C5—O1	1.80 (13)
O1—C1—C2—C3	55.36 (11)	C9—C4—C5—C6	0.23 (13)
C1—C2—C3—O2	154.40 (10)	C3—C4—C5—C6	−177.25 (8)
C1—C2—C3—C4	−26.96 (11)	O1—C5—C6—C7	−179.64 (9)
O2—C3—C4—C5	177.76 (9)	C4—C5—C6—C7	−0.55 (14)
C2—C3—C4—C5	−0.88 (12)	C5—C6—C7—C8	0.14 (15)
O2—C3—C4—C9	0.32 (14)	C6—C7—C8—C9	0.60 (16)
C2—C3—C4—C9	−178.33 (8)	C7—C8—C9—C4	−0.93 (15)
C1—O1—C5—C6	−153.72 (9)	C5—C4—C9—C8	0.52 (14)
C1—O1—C5—C4	27.22 (12)	C3—C4—C9—C8	177.99 (8)
C9—C4—C5—O1	179.27 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H11···O2ⁱ	0.99	2.53	3.4674 (13)	157
C1—H12···O2ⁱⁱ	0.99	2.56	3.3934 (15)	141

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₈O₂
M_r	148.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	7.5538 (4), 8.0896 (4), 13.0410 (6)
β (°)	115.364 (3)
V (Å³)	720.08 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.41 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6367, 1774, 1578
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.05
No. of reflections	1774
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.19

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae, et al., 2006), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H11···O2ⁱ	0.99	2.53	3.4674 (13)	157
C1—H12···O2ⁱⁱ	0.99	2.56	3.3934 (15)	141

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

The authors thank Mr Raynard Fourie for helpful discussions.

References

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