3,4-Di­hydro-1H-benzo[c]chromene-1,6(2H)-dione

In the title compound, C₁₃H₁₀O₃, the pyran­one and benzene rings are almost coplanar, making a dihedral angle of 1.9 (1)°. The cyclo­hexenone ring adopts an envelope conformation, with a methyl­ene C atom located at the flap and displaced by 0.639 (3) Å from the mean plane of the other five atoms. In the crystal, pairs of weak C—H⋯π inter­actions occur between inversion-related mol­ecules.

Related literature

For applications of benzo[c]chromen-6-ones, see: Schmidt et al. (2003); Pandey et al. (2004); Matsumoto & Hanawalt (2000); Sun et al. (2006). For the synthesis, see: Fan et al. (2012).

Experimental

Crystal data

• C₁₃H₁₀O₃

• M_r = 214.21

• Monoclinic, P 2₁ /c

• a = 8.234 (3) Å

• b = 10.199 (3) Å

• c = 11.927 (4) Å

• β = 97.439 (4)°

• V = 993.1 (6) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 296 K

• 0.47 × 0.41 × 0.31 mm

Data collection

• Bruker SMART 1000 CCD area-detector diffractometer

• 6998 measured reflections

• 1843 independent reflections

• 1517 reflections with I > 2σ(I)

• R_int = 0.027

Refinement

• R[F² > 2σ(F²)] = 0.077

• wR(F²) = 0.229

• S = 1.18

• 1843 reflections

• 145 parameters

• H-atom parameters constrained

• Δρ_max = 0.33 e Å⁻³

• Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯Cg^i	0.97	2.91	3.723 (5)	142
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

S1. Comment

Benzo[c]chromen-6-ones constitute one of the major classes of pharmacologically relevant natural products and display a wide range of biological activities (Schmidt et al., 2003; Pandey et al., 2004; Matsumoto et al., 2000; Sun et al., 2006). As part of our research (Fan et al. 2012), we have synthesized the title compound (I), and report its crystal structure here.

The title compound, C₁₃H₁₀O₃, consists of three fused six-membered rings, benzene, pyranone and cyclohexenone ring. The pyranone ring is in the middle. All the bond lengths and bond angles are within normal ranges. The pyranone ring and the benzene ring are almost coplanar with a dihedral angle of 1.9 (1) °. The cyclohexenone ring adopts an envelope conformation, a methylene C atom located on the flap and displaced from the mean plane of the other five ring atoms (C8—C11/C13) by 0.639 (3) Å.

In the crystal, weak intermolecular C—H···π interactions occur between benzene ring and methylene group of adjacent molecules, the separation between the centroid of benzene ring and methylene H atom being 2.91 Å.

Related literature

For applications of benzo[c]chromen-6-ones, see: Schmidt et al. (2003); Pandey et al. (2004); Matsumoto & Hanawalt (2000); Sun et al. (2006). For the synthesis, see: Fan et al. (2012).

S2. Experimental

The title compound was synthesized following the previously reported procedure (Fan et al., 2012). Single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvents from a petroleum ether-ethyl acetate (5:1 v/v) solution of the title compound.

S3. Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93–0.97 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound with view along the b axis.

3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

Crystal data

C13H10O3	F(000) = 448
Mr = 214.21	Dx = 1.433 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2699 reflections
a = 8.234 (3) Å	θ = 2.5–27.2°
b = 10.199 (3) Å	µ = 0.10 mm^−1
c = 11.927 (4) Å	T = 296 K
β = 97.439 (4)°	Block, colorless
V = 993.1 (6) Å^3	0.47 × 0.41 × 0.31 mm
Z = 4

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1517 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.5°, θmin = 2.5°
φ and ω scans	h = −9→9
6998 measured reflections	k = −12→12
1843 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.229	H-atom parameters constrained
S = 1.18	w = 1/[σ^2(Fo^2) + (0.0741P)^2 + 2.0297P] where P = (Fo^2 + 2Fc^2)/3
1843 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.1515 (4)	0.4254 (4)	0.4108 (3)	0.0372 (8)
C2	0.0900 (5)	0.2983 (4)	0.3970 (4)	0.0462 (10)
H2	0.0294	0.2737	0.3290	0.055*
C3	0.1189 (5)	0.2095 (4)	0.4836 (4)	0.0556 (11)
H3	0.0797	0.1242	0.4741	0.067*
C4	0.2063 (6)	0.2472 (5)	0.5847 (4)	0.0577 (12)
H4	0.2239	0.1871	0.6437	0.069*
C5	0.2681 (5)	0.3725 (4)	0.6002 (3)	0.0494 (10)
H5	0.3266	0.3958	0.6693	0.059*
C6	0.2435 (4)	0.4652 (4)	0.5127 (3)	0.0361 (8)
C7	0.1173 (5)	0.5166 (4)	0.3171 (3)	0.0409 (9)
C8	0.2628 (4)	0.6829 (4)	0.4336 (3)	0.0388 (9)
C9	0.3044 (4)	0.6001 (4)	0.5209 (3)	0.0364 (8)
C10	0.4169 (5)	0.6504 (4)	0.6187 (3)	0.0448 (10)
C11	0.4572 (6)	0.7945 (5)	0.6214 (4)	0.0575 (12)
H11A	0.4649	0.8249	0.6990	0.069*
H11B	0.5640	0.8061	0.5967	0.069*
C12	0.3362 (5)	0.8789 (4)	0.5496 (4)	0.0522 (11)
H12A	0.3787	0.9675	0.5474	0.063*
H12B	0.2345	0.8823	0.5824	0.063*
C13	0.3036 (6)	0.8247 (4)	0.4302 (4)	0.0517 (11)
H13A	0.2133	0.8719	0.3880	0.062*
H13B	0.3998	0.8366	0.3922	0.062*
O1	0.0424 (4)	0.4948 (3)	0.2258 (2)	0.0618 (9)
O2	0.1742 (3)	0.6438 (3)	0.3351 (2)	0.0457 (7)
O3	0.4831 (4)	0.5785 (3)	0.6928 (2)	0.0663 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0344 (18)	0.038 (2)	0.0388 (19)	0.0033 (15)	0.0045 (14)	−0.0020 (15)
C2	0.039 (2)	0.043 (2)	0.055 (2)	−0.0017 (17)	0.0025 (17)	−0.0056 (18)
C3	0.050 (2)	0.040 (2)	0.078 (3)	−0.0044 (19)	0.010 (2)	0.006 (2)
C4	0.063 (3)	0.051 (3)	0.059 (3)	0.002 (2)	0.009 (2)	0.018 (2)
C5	0.053 (2)	0.052 (2)	0.041 (2)	0.001 (2)	0.0006 (18)	0.0082 (18)
C6	0.0314 (18)	0.041 (2)	0.0354 (18)	0.0056 (15)	0.0039 (14)	0.0009 (15)
C7	0.045 (2)	0.041 (2)	0.0347 (19)	0.0033 (16)	−0.0020 (16)	−0.0043 (16)
C8	0.0409 (19)	0.039 (2)	0.0356 (18)	0.0035 (16)	0.0010 (15)	−0.0034 (15)
C9	0.0349 (18)	0.040 (2)	0.0346 (18)	0.0041 (15)	0.0049 (14)	−0.0041 (15)
C10	0.042 (2)	0.055 (2)	0.037 (2)	−0.0001 (18)	0.0021 (16)	−0.0071 (18)
C11	0.052 (2)	0.064 (3)	0.055 (3)	−0.011 (2)	0.000 (2)	−0.016 (2)
C12	0.052 (2)	0.041 (2)	0.064 (3)	−0.0074 (19)	0.009 (2)	−0.012 (2)
C13	0.061 (3)	0.038 (2)	0.055 (2)	−0.0033 (19)	0.004 (2)	0.0006 (19)
O1	0.081 (2)	0.0545 (19)	0.0429 (16)	0.0025 (16)	−0.0182 (15)	−0.0078 (14)
O2	0.0594 (17)	0.0378 (15)	0.0365 (14)	0.0017 (12)	−0.0069 (12)	−0.0001 (11)
O3	0.074 (2)	0.076 (2)	0.0433 (17)	−0.0031 (18)	−0.0168 (15)	0.0024 (16)

Geometric parameters (Å, º)

C1—C2	1.393 (5)	C8—C9	1.349 (5)
C1—C6	1.406 (5)	C8—O2	1.360 (4)
C1—C7	1.454 (5)	C8—C13	1.486 (5)
C2—C3	1.372 (6)	C9—C10	1.484 (5)
C2—H2	0.9300	C10—O3	1.222 (5)
C3—C4	1.376 (6)	C10—C11	1.506 (6)
C3—H3	0.9300	C11—C12	1.499 (6)
C4—C5	1.379 (6)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.403 (5)	C12—C13	1.519 (6)
C5—H5	0.9300	C12—H12A	0.9700
C6—C9	1.463 (5)	C12—H12B	0.9700
C7—O1	1.201 (4)	C13—H13A	0.9700
C7—O2	1.387 (5)	C13—H13B	0.9700
C2—C1—C6	121.2 (3)	C8—C9—C10	117.4 (3)
C2—C1—C7	118.3 (3)	C6—C9—C10	123.5 (3)
C6—C1—C7	120.6 (3)	O3—C10—C9	122.4 (4)
C3—C2—C1	120.1 (4)	O3—C10—C11	119.6 (4)
C3—C2—H2	120.0	C9—C10—C11	117.9 (4)
C1—C2—H2	120.0	C12—C11—C10	114.8 (3)
C2—C3—C4	119.7 (4)	C12—C11—H11A	108.6
C2—C3—H3	120.2	C10—C11—H11A	108.6
C4—C3—H3	120.2	C12—C11—H11B	108.6
C3—C4—C5	121.2 (4)	C10—C11—H11B	108.6
C3—C4—H4	119.4	H11A—C11—H11B	107.5
C5—C4—H4	119.4	C11—C12—C13	110.5 (4)
C4—C5—C6	120.6 (4)	C11—C12—H12A	109.6
C4—C5—H5	119.7	C13—C12—H12A	109.6
C6—C5—H5	119.7	C11—C12—H12B	109.6
C5—C6—C1	117.2 (4)	C13—C12—H12B	109.6
C5—C6—C9	124.6 (3)	H12A—C12—H12B	108.1
C1—C6—C9	118.1 (3)	C8—C13—C12	110.0 (3)
O1—C7—O2	115.9 (3)	C8—C13—H13A	109.7
O1—C7—C1	127.2 (4)	C12—C13—H13A	109.7
O2—C7—C1	116.9 (3)	C8—C13—H13B	109.7
C9—C8—O2	122.5 (3)	C12—C13—H13B	109.7
C9—C8—C13	126.5 (3)	H13A—C13—H13B	108.2
O2—C8—C13	111.0 (3)	C8—O2—C7	122.7 (3)
C8—C9—C6	119.1 (3)
C6—C1—C2—C3	0.0 (6)	C5—C6—C9—C8	−175.2 (4)
C7—C1—C2—C3	−179.7 (4)	C1—C6—C9—C8	3.7 (5)
C1—C2—C3—C4	1.1 (6)	C5—C6—C9—C10	7.6 (6)
C2—C3—C4—C5	−1.1 (7)	C1—C6—C9—C10	−173.5 (3)
C3—C4—C5—C6	−0.1 (7)	C8—C9—C10—O3	−167.7 (4)
C4—C5—C6—C1	1.2 (6)	C6—C9—C10—O3	9.5 (6)
C4—C5—C6—C9	−179.8 (4)	C8—C9—C10—C11	8.5 (5)
C2—C1—C6—C5	−1.1 (5)	C6—C9—C10—C11	−174.2 (3)
C7—C1—C6—C5	178.5 (3)	O3—C10—C11—C12	−162.4 (4)
C2—C1—C6—C9	179.8 (3)	C9—C10—C11—C12	21.2 (6)
C7—C1—C6—C9	−0.5 (5)	C10—C11—C12—C13	−51.1 (5)
C2—C1—C7—O1	−1.2 (6)	C9—C8—C13—C12	−23.3 (6)
C6—C1—C7—O1	179.1 (4)	O2—C8—C13—C12	156.4 (3)
C2—C1—C7—O2	177.4 (3)	C11—C12—C13—C8	50.7 (5)
C6—C1—C7—O2	−2.3 (5)	C9—C8—O2—C7	1.1 (6)
O2—C8—C9—C6	−4.1 (5)	C13—C8—O2—C7	−178.6 (3)
C13—C8—C9—C6	175.5 (4)	O1—C7—O2—C8	−179.1 (4)
O2—C8—C9—C10	173.2 (3)	C1—C7—O2—C8	2.2 (5)
C13—C8—C9—C10	−7.1 (6)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cg^i	0.97	2.91	3.723 (5)	142

Symmetry code: (i) −x+1, −y+1, −z+1.