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

In the title compound, C(9)H(8)O(2), a benzo-annulated heterocyclic ketone, the non-aromatic six-membered ring adopts an E(2) conformation. In the crystal, C-H⋯O contacts connect the mol-ecules 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 = 148.15

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.05

1774 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.19 e Å−3

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 ▶).

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

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

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

C9H8O2	F(000) = 312
Mr = 148.15	Dx = 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

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

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(Fo2) + (0.0588P)2 + 0.1339P] where P = (Fo2 + 2Fc2)/3
1774 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .