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

In the title compound, C13H10O3, the pyran-one and benzene rings are almost coplanar, making a dihedral angle of 1.9 (1)°. The cyclo-hexenone ring adopts an envelope conformation, with a methyl-ene 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 inter-actions occur between inversion-related mol-ecules.

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 = 214.21

Monoclinic,

a = 8.234 (3) Å

b = 10.199 (3) Å

c = 11.927 (4) Å

β = 97.439 (4)°

V = 993.1 (6) Å3

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[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.229

S = 1.18

1843 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010210/xu5693sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010210/xu5693Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010210/xu5693Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010210/xu5693Isup4.cml

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

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) Å3	0.47 × 0.41 × 0.31 mm
Z = 4

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 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0741P)2 + 2.0297P] where P = (Fo2 + 2Fc2)/3
1843 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	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)

	U11	U22	U33	U12	U13	U23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···Cgi	0.97	2.91	3.723 (5)	142

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) .