10-Phenyl-6b,7,8,9,9a,10-hexa-hydro-6H-cyclo-penta-[4,5]pyrano[3,2-c]chromen-6,9-dione.

In the title compound, C(21)H(16)O(4), the dihedral angle between the phenyl ring and the 2H-chromene ring system is 59.8 (2)°. The crystal packing is stabilized by weak π-π stacking inter-actions [centroid-centroid distances = 3.667 (2) Å] and inter-molecular C-H⋯O hydrogen-bonding inter-actions.

Related literature

For applications of coumarin, see: Vu et al. (2008 ▶); Maresca et al. (2009 ▶); Maresca et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H16O4

M = 332.34

Monoclinic,

a = 9.1672 (14) Å

b = 8.6538 (14) Å

c = 19.899 (3) Å

β = 91.295 (3)°

V = 1578.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.50 × 0.50 × 0.41 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: numerical (CrystalClear; Rigaku, 2007 ▶) T min = 0.953, T max = 0.961

13128 measured reflections

3608 independent reflections

3469 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.144

S = 1.10

3608 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006192/hg2800sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006192/hg2800Isup2.hkl

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

C21H16O4	F(000) = 696
Mr = 332.34	Dx = 1.399 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4768 reflections
a = 9.1672 (14) Å	θ = 1.0–27.5°
b = 8.6538 (14) Å	µ = 0.10 mm−1
c = 19.899 (3) Å	T = 173 K
β = 91.295 (3)°	Block, colorless
V = 1578.2 (4) Å3	0.50 × 0.50 × 0.41 mm
Z = 4

Rigaku Saturn724+ CCD diffractometer	3608 independent reflections
Radiation source: sealed tube	3469 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans at fixed χ = 45°	θmax = 27.5°, θmin = 3.1°
Absorption correction: numerical (CrystalClear; Rigaku, 2007)	h = −11→11
Tmin = 0.953, Tmax = 0.961	k = −10→11
13128 measured reflections	l = −22→25

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.6329P] where P = (Fo2 + 2Fc2)/3
3608 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.22 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
O1	0.50827 (10)	0.14483 (13)	0.10143 (5)	0.0292 (2)
O2	0.30494 (11)	0.31578 (13)	−0.06936 (5)	0.0342 (3)
O3	0.21059 (14)	−0.10952 (16)	0.24113 (6)	0.0472 (3)
O4	0.09368 (13)	0.21341 (18)	−0.04206 (7)	0.0509 (4)
C1	0.45295 (15)	0.33318 (17)	−0.05937 (7)	0.0293 (3)
C2	0.52778 (18)	0.41320 (18)	−0.10830 (8)	0.0344 (3)
H2A	0.4773	0.4543	−0.1465	0.041*
C3	0.67665 (18)	0.43206 (18)	−0.10057 (8)	0.0358 (3)
H3A	0.7289	0.4869	−0.1337	0.043*
C4	0.75115 (17)	0.37144 (19)	−0.04468 (8)	0.0358 (3)
H4A	0.8538	0.3846	−0.0400	0.043*
C5	0.67574 (16)	0.29218 (18)	0.00397 (8)	0.0321 (3)
H5A	0.7267	0.2512	0.0420	0.039*
C6	0.52458 (15)	0.27221 (16)	−0.00277 (7)	0.0268 (3)
C7	0.43568 (15)	0.19240 (16)	0.04545 (7)	0.0260 (3)
C8	0.41941 (15)	0.10574 (17)	0.15850 (7)	0.0275 (3)
H8A	0.3765	0.2025	0.1771	0.033*
C9	0.29535 (15)	−0.00278 (17)	0.13564 (7)	0.0289 (3)
H9A	0.3352	−0.1037	0.1198	0.035*
C10	0.18782 (18)	−0.02793 (19)	0.19294 (8)	0.0356 (3)
C11	0.0505 (2)	0.0604 (3)	0.17786 (11)	0.0564 (5)
H11A	0.0224	0.1227	0.2173	0.068*
H11B	−0.0305	−0.0110	0.1661	0.068*
C12	0.08425 (18)	0.1647 (2)	0.11868 (9)	0.0412 (4)
H12A	0.1231	0.2656	0.1342	0.049*
H12B	−0.0039	0.1824	0.0900	0.049*
C13	0.20060 (15)	0.07317 (18)	0.08039 (7)	0.0308 (3)
H13A	0.1506	−0.0100	0.0537	0.037*
C14	0.29132 (15)	0.16801 (17)	0.03381 (7)	0.0285 (3)
C15	0.22106 (16)	0.22987 (19)	−0.02619 (8)	0.0343 (3)
C16	0.51992 (15)	0.03462 (17)	0.21074 (7)	0.0274 (3)
C17	0.62801 (17)	−0.06787 (19)	0.19234 (8)	0.0360 (3)
H17A	0.6423	−0.0896	0.1462	0.043*
C18	0.71543 (18)	−0.1389 (2)	0.24094 (9)	0.0440 (4)
H18A	0.7886	−0.2101	0.2280	0.053*
C19	0.69637 (19)	−0.1066 (2)	0.30784 (9)	0.0453 (4)
H19A	0.7564	−0.1553	0.3411	0.054*
C20	0.59009 (19)	−0.0033 (2)	0.32673 (8)	0.0413 (4)
H20A	0.5775	0.0194	0.3729	0.050*
C21	0.50157 (17)	0.06724 (18)	0.27822 (7)	0.0325 (3)
H21A	0.4283	0.1380	0.2913	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0241 (5)	0.0389 (6)	0.0247 (5)	−0.0026 (4)	0.0003 (4)	0.0033 (4)
O2	0.0283 (5)	0.0438 (6)	0.0306 (5)	0.0048 (4)	0.0013 (4)	0.0074 (4)
O3	0.0493 (7)	0.0534 (8)	0.0387 (6)	−0.0192 (6)	0.0001 (5)	0.0139 (5)
O4	0.0280 (6)	0.0765 (10)	0.0478 (7)	−0.0013 (6)	−0.0061 (5)	0.0182 (6)
C1	0.0289 (7)	0.0296 (7)	0.0295 (7)	0.0032 (5)	0.0043 (5)	−0.0011 (5)
C2	0.0418 (8)	0.0309 (7)	0.0307 (7)	0.0054 (6)	0.0077 (6)	0.0029 (6)
C3	0.0416 (8)	0.0309 (7)	0.0356 (8)	−0.0024 (6)	0.0145 (6)	0.0004 (6)
C4	0.0303 (7)	0.0372 (8)	0.0402 (8)	−0.0051 (6)	0.0093 (6)	−0.0060 (6)
C5	0.0281 (7)	0.0369 (8)	0.0315 (7)	−0.0019 (6)	0.0028 (5)	−0.0040 (6)
C6	0.0261 (7)	0.0279 (7)	0.0264 (6)	0.0002 (5)	0.0044 (5)	−0.0029 (5)
C7	0.0256 (6)	0.0274 (7)	0.0251 (6)	0.0016 (5)	0.0007 (5)	−0.0012 (5)
C8	0.0263 (6)	0.0307 (7)	0.0256 (6)	−0.0004 (5)	0.0042 (5)	−0.0006 (5)
C9	0.0291 (7)	0.0273 (7)	0.0303 (7)	−0.0015 (5)	0.0017 (5)	−0.0004 (5)
C10	0.0367 (8)	0.0374 (8)	0.0327 (7)	−0.0132 (6)	0.0032 (6)	0.0016 (6)
C11	0.0377 (9)	0.0749 (14)	0.0572 (11)	0.0069 (9)	0.0193 (8)	0.0207 (10)
C12	0.0290 (7)	0.0491 (10)	0.0460 (9)	0.0061 (7)	0.0093 (6)	0.0064 (7)
C13	0.0251 (7)	0.0342 (7)	0.0332 (7)	−0.0023 (5)	0.0004 (5)	0.0018 (6)
C14	0.0261 (7)	0.0326 (7)	0.0269 (6)	0.0019 (5)	0.0023 (5)	0.0009 (5)
C15	0.0266 (7)	0.0431 (9)	0.0333 (7)	0.0032 (6)	0.0009 (6)	0.0046 (6)
C16	0.0270 (6)	0.0284 (7)	0.0267 (7)	−0.0024 (5)	0.0001 (5)	−0.0003 (5)
C17	0.0346 (8)	0.0390 (8)	0.0345 (8)	0.0058 (6)	0.0007 (6)	−0.0031 (6)
C18	0.0330 (8)	0.0438 (9)	0.0550 (10)	0.0062 (7)	−0.0019 (7)	0.0089 (8)
C19	0.0363 (8)	0.0534 (10)	0.0456 (9)	−0.0102 (7)	−0.0133 (7)	0.0196 (8)
C20	0.0456 (9)	0.0494 (10)	0.0288 (7)	−0.0187 (8)	−0.0053 (6)	0.0039 (7)
C21	0.0363 (8)	0.0328 (7)	0.0287 (7)	−0.0073 (6)	0.0031 (6)	−0.0022 (6)

O1—C7	1.3491 (17)	C9—H9A	1.0000
O1—C8	1.4524 (16)	C10—C11	1.498 (3)
O2—C1	1.3751 (17)	C11—C12	1.521 (3)
O2—C15	1.3828 (18)	C11—H11A	0.9900
O3—C10	1.205 (2)	C11—H11B	0.9900
O4—C15	1.2112 (19)	C12—C13	1.543 (2)
C1—C2	1.389 (2)	C12—H12A	0.9900
C1—C6	1.394 (2)	C12—H12B	0.9900
C2—C3	1.380 (2)	C13—C14	1.503 (2)
C2—H2A	0.9500	C13—H13A	1.0000
C3—C4	1.394 (2)	C14—C15	1.446 (2)
C3—H3A	0.9500	C16—C17	1.385 (2)
C4—C5	1.384 (2)	C16—C21	1.386 (2)
C4—H4A	0.9500	C17—C18	1.386 (2)
C5—C6	1.3999 (19)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.375 (3)
C6—C7	1.4483 (19)	C18—H18A	0.9500
C7—C14	1.3548 (19)	C19—C20	1.380 (3)
C8—C16	1.5050 (19)	C19—H19A	0.9500
C8—C9	1.5359 (19)	C20—C21	1.388 (2)
C8—H8A	1.0000	C20—H20A	0.9500
C9—C13	1.534 (2)	C21—H21A	0.9500
C9—C10	1.540 (2)
C7—O1—C8	116.22 (10)	C12—C11—H11A	110.6
C1—O2—C15	121.99 (11)	C10—C11—H11B	110.6
O2—C1—C2	117.04 (13)	C12—C11—H11B	110.6
O2—C1—C6	121.37 (12)	H11A—C11—H11B	108.7
C2—C1—C6	121.59 (14)	C11—C12—C13	103.48 (14)
C3—C2—C1	118.94 (14)	C11—C12—H12A	111.1
C3—C2—H2A	120.5	C13—C12—H12A	111.1
C1—C2—H2A	120.5	C11—C12—H12B	111.1
C2—C3—C4	120.66 (14)	C13—C12—H12B	111.1
C2—C3—H3A	119.7	H12A—C12—H12B	109.0
C4—C3—H3A	119.7	C14—C13—C9	111.33 (12)
C5—C4—C3	120.06 (14)	C14—C13—C12	114.99 (13)
C5—C4—H4A	120.0	C9—C13—C12	104.62 (12)
C3—C4—H4A	120.0	C14—C13—H13A	108.6
C4—C5—C6	120.20 (14)	C9—C13—H13A	108.6
C4—C5—H5A	119.9	C12—C13—H13A	108.6
C6—C5—H5A	119.9	C7—C14—C15	119.90 (13)
C1—C6—C5	118.54 (13)	C7—C14—C13	122.11 (13)
C1—C6—C7	116.98 (12)	C15—C14—C13	117.96 (13)
C5—C6—C7	124.48 (13)	O4—C15—O2	116.59 (14)
O1—C7—C14	123.74 (13)	O4—C15—C14	125.49 (15)
O1—C7—C6	114.72 (12)	O2—C15—C14	117.93 (13)
C14—C7—C6	121.54 (13)	C17—C16—C21	119.32 (14)
O1—C8—C16	106.85 (11)	C17—C16—C8	120.64 (13)
O1—C8—C9	109.60 (11)	C21—C16—C8	120.00 (13)
C16—C8—C9	113.09 (12)	C16—C17—C18	120.36 (15)
O1—C8—H8A	109.1	C16—C17—H17A	119.8
C16—C8—H8A	109.1	C18—C17—H17A	119.8
C9—C8—H8A	109.1	C19—C18—C17	120.06 (17)
C13—C9—C8	110.72 (12)	C19—C18—H18A	120.0
C13—C9—C10	103.28 (12)	C17—C18—H18A	120.0
C8—C9—C10	110.45 (12)	C18—C19—C20	120.08 (15)
C13—C9—H9A	110.7	C18—C19—H19A	120.0
C8—C9—H9A	110.7	C20—C19—H19A	120.0
C10—C9—H9A	110.7	C19—C20—C21	120.03 (15)
O3—C10—C11	126.03 (15)	C19—C20—H20A	120.0
O3—C10—C9	124.73 (16)	C21—C20—H20A	120.0
C11—C10—C9	109.21 (13)	C16—C21—C20	120.14 (15)
C10—C11—C12	105.83 (13)	C16—C21—H21A	119.9
C10—C11—H11A	110.6	C20—C21—H21A	119.9
C15—O2—C1—C2	175.79 (14)	C8—C9—C13—C14	36.94 (16)
C15—O2—C1—C6	−3.8 (2)	C10—C9—C13—C14	155.18 (12)
O2—C1—C2—C3	−179.40 (13)	C8—C9—C13—C12	−87.86 (14)
C6—C1—C2—C3	0.2 (2)	C10—C9—C13—C12	30.38 (15)
C1—C2—C3—C4	0.2 (2)	C11—C12—C13—C14	−159.98 (15)
C2—C3—C4—C5	−0.4 (2)	C11—C12—C13—C9	−37.54 (17)
C3—C4—C5—C6	0.1 (2)	O1—C7—C14—C15	176.95 (13)
O2—C1—C6—C5	179.16 (13)	C6—C7—C14—C15	−3.5 (2)
C2—C1—C6—C5	−0.4 (2)	O1—C7—C14—C13	−5.1 (2)
O2—C1—C6—C7	−1.1 (2)	C6—C7—C14—C13	174.40 (13)
C2—C1—C6—C7	179.32 (13)	C9—C13—C14—C7	−6.2 (2)
C4—C5—C6—C1	0.3 (2)	C12—C13—C14—C7	112.55 (16)
C4—C5—C6—C7	−179.48 (14)	C9—C13—C14—C15	171.73 (13)
C8—O1—C7—C14	−17.6 (2)	C12—C13—C14—C15	−69.51 (18)
C8—O1—C7—C6	162.78 (12)	C1—O2—C15—O4	−175.20 (15)
C1—C6—C7—O1	−175.67 (12)	C1—O2—C15—C14	5.1 (2)
C5—C6—C7—O1	4.1 (2)	C7—C14—C15—O4	178.92 (16)
C1—C6—C7—C14	4.7 (2)	C13—C14—C15—O4	0.9 (3)
C5—C6—C7—C14	−175.52 (14)	C7—C14—C15—O2	−1.4 (2)
C7—O1—C8—C16	171.88 (11)	C13—C14—C15—O2	−179.35 (13)
C7—O1—C8—C9	49.00 (16)	O1—C8—C16—C17	−40.89 (18)
O1—C8—C9—C13	−58.49 (15)	C9—C8—C16—C17	79.79 (17)
C16—C8—C9—C13	−177.59 (11)	O1—C8—C16—C21	141.38 (13)
O1—C8—C9—C10	−172.27 (12)	C9—C8—C16—C21	−97.94 (15)
C16—C8—C9—C10	68.63 (15)	C21—C16—C17—C18	1.0 (2)
C13—C9—C10—O3	165.87 (15)	C8—C16—C17—C18	−176.74 (15)
C8—C9—C10—O3	−75.70 (19)	C16—C17—C18—C19	−0.8 (3)
C13—C9—C10—C11	−12.28 (18)	C17—C18—C19—C20	0.1 (3)
C8—C9—C10—C11	106.14 (16)	C18—C19—C20—C21	0.4 (3)
O3—C10—C11—C12	170.98 (17)	C17—C16—C21—C20	−0.5 (2)
C9—C10—C11—C12	−10.9 (2)	C8—C16—C21—C20	177.23 (13)
C10—C11—C12—C13	29.6 (2)	C19—C20—C21—C16	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3i	1.00	2.45	3.4042 (19)	160
C17—H17A···O2ii	0.95	2.54	3.322 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O3i	1.00	2.45	3.4042 (19)	160
C17—H17A⋯O2ii	0.95	2.54	3.322 (2)	140

Symmetry codes: (i) ; (ii) .