3,9-Dimethyl-2,3-dihydro-phenanthro[1,2-b]furan-4,5-dione.

The title compound, C(18)H(14)O(3), consists of a four-ring system which contains three six-membered rings forming a phenanthrene-dione system and a five-membered 1,2-dihydro-methyl-furan ring. A three-dimensional supra-molecular framework is formed via non-classical inter-molecular C-H⋯O hydrogen bonds.

Related literature

For tanshinone compounds, see: Chang et al. (1991 ▶); Ryu et al. (1997 ▶); Xue et al. (1999 ▶); Yagi et al. (1989 ▶); Zhang et al. (2005 ▶); Zhu & Luo (2004 ▶).

Experimental

Crystal data

C18H14O3

M = 278.29

Orthorhombic,

a = 4.6415 (10) Å

b = 14.692 (3) Å

c = 19.633 (4) Å

V = 1338.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.25 × 0.10 × 0.05 mm

Data collection

Bruker or SMART APEXdiffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.995

6925 measured reflections

2502 independent reflections

1140 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.077

S = 1.03

2502 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047667/rk2163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047667/rk2163Isup2.hkl

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

C18H14O3	F(000) = 584
Mr = 278.29	Dx = 1.381 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 634 reflections
a = 4.6415 (10) Å	θ = 2.5–18.2°
b = 14.692 (3) Å	µ = 0.09 mm−1
c = 19.633 (4) Å	T = 295 K
V = 1338.8 (5) Å3	Block, yellow
Z = 4	0.25 × 0.10 × 0.05 mm

Bruker SMART APEX diffractometer	2502 independent reflections
Radiation source: fine-focus sealed tube	1140 reflections with I > 2σ(I)
graphite	Rint = 0.079
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→5
Tmin = 0.977, Tmax = 0.995	k = −16→17
6925 measured reflections	l = −23→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0115P)2] where P = (Fo2 + 2Fc2)/3
2502 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.9141 (6)	0.38978 (16)	0.80968 (12)	0.0805 (9)
O2	0.5033 (6)	0.47076 (16)	0.73687 (12)	0.0795 (9)
O3	0.5747 (6)	0.72625 (16)	0.87005 (12)	0.0692 (8)
C1	1.4263 (9)	0.4722 (3)	1.04455 (18)	0.0556 (10)
C2	1.5314 (9)	0.3891 (3)	1.03047 (19)	0.0667 (12)
H2	1.6605	0.3621	1.0605	0.080*
C3	1.4497 (9)	0.3423 (2)	0.9711 (2)	0.0657 (12)
H3	1.5261	0.2849	0.9628	0.079*
C4	1.2618 (8)	0.3789 (2)	0.92557 (19)	0.0569 (11)
H4	1.2110	0.3464	0.8867	0.068*
C5	1.1438 (8)	0.4660 (2)	0.93705 (17)	0.0448 (10)
C6	1.2314 (8)	0.5139 (3)	0.99724 (17)	0.0467 (10)
C7	1.1235 (9)	0.6017 (3)	1.00860 (17)	0.0574 (11)
H7	1.1801	0.6331	1.0475	0.069*
C8	0.9366 (9)	0.6424 (2)	0.96396 (18)	0.0597 (12)
H8	0.8690	0.7009	0.9724	0.072*
C9	0.8490 (8)	0.5959 (2)	0.90615 (18)	0.0485 (10)
C10	0.9455 (8)	0.5084 (2)	0.89194 (16)	0.0441 (9)
C11	0.8348 (8)	0.4632 (3)	0.82957 (18)	0.0508 (10)
C12	0.6103 (9)	0.5125 (2)	0.78450 (18)	0.0547 (11)
C13	0.5429 (8)	0.6037 (2)	0.80144 (18)	0.0482 (10)
C14	0.6529 (8)	0.6393 (2)	0.8583 (2)	0.0514 (11)
C15	0.3586 (8)	0.6724 (2)	0.76485 (18)	0.0610 (11)
H15	0.1590	0.6507	0.7634	0.073*
C16	0.3806 (9)	0.7536 (3)	0.81363 (19)	0.0889 (14)
H16A	0.4581	0.8062	0.7901	0.107*
H16B	0.1917	0.7692	0.8313	0.107*
C17	1.5136 (8)	0.5226 (3)	1.10832 (15)	0.0772 (13)
H17A	1.3472	0.5322	1.1365	0.116*
H17B	1.5959	0.5803	1.0962	0.116*
H17C	1.6532	0.4873	1.1329	0.116*
C18	0.4609 (9)	0.6927 (2)	0.69344 (17)	0.0875 (15)
H18A	0.6569	0.7135	0.6949	0.131*
H18B	0.3414	0.7391	0.6737	0.131*
H18C	0.4494	0.6385	0.6663	0.131*

	U11	U22	U33	U12	U13	U23
O1	0.106 (2)	0.0545 (17)	0.0810 (19)	0.0212 (18)	−0.0224 (18)	−0.0241 (15)
O2	0.096 (2)	0.0665 (18)	0.0754 (19)	−0.0015 (18)	−0.0249 (18)	−0.0080 (16)
O3	0.089 (2)	0.0457 (16)	0.0727 (18)	0.0135 (17)	−0.0073 (16)	−0.0040 (14)
C1	0.053 (3)	0.065 (3)	0.049 (3)	−0.011 (3)	0.000 (2)	−0.001 (2)
C2	0.064 (3)	0.074 (3)	0.062 (3)	0.004 (3)	−0.005 (2)	0.007 (3)
C3	0.070 (3)	0.053 (3)	0.073 (3)	0.010 (3)	−0.002 (3)	−0.002 (2)
C4	0.063 (3)	0.047 (3)	0.061 (3)	0.005 (2)	−0.001 (2)	−0.003 (2)
C5	0.044 (2)	0.044 (2)	0.047 (2)	−0.008 (2)	0.009 (2)	0.001 (2)
C6	0.047 (2)	0.047 (3)	0.045 (2)	−0.008 (2)	0.009 (2)	−0.001 (2)
C7	0.068 (3)	0.053 (3)	0.052 (3)	−0.009 (3)	0.004 (2)	−0.015 (2)
C8	0.075 (3)	0.045 (2)	0.059 (3)	0.000 (2)	0.000 (3)	−0.012 (2)
C9	0.054 (3)	0.040 (2)	0.052 (3)	−0.003 (2)	0.006 (2)	0.001 (2)
C10	0.049 (2)	0.042 (2)	0.041 (2)	−0.005 (2)	0.009 (2)	−0.004 (2)
C11	0.052 (3)	0.044 (2)	0.056 (3)	0.002 (2)	0.004 (2)	0.000 (2)
C12	0.060 (3)	0.050 (3)	0.054 (3)	−0.009 (2)	0.000 (2)	0.000 (2)
C13	0.055 (3)	0.041 (2)	0.049 (2)	−0.005 (2)	0.007 (2)	0.005 (2)
C14	0.060 (3)	0.032 (2)	0.063 (3)	0.002 (2)	0.016 (2)	0.000 (2)
C15	0.058 (3)	0.058 (3)	0.067 (3)	0.003 (2)	0.001 (2)	0.007 (2)
C16	0.111 (4)	0.065 (3)	0.091 (3)	0.029 (3)	−0.024 (3)	0.004 (3)
C17	0.078 (3)	0.099 (3)	0.055 (2)	−0.002 (3)	−0.010 (2)	−0.008 (2)
C18	0.113 (4)	0.078 (3)	0.071 (3)	0.024 (3)	0.020 (3)	0.023 (2)

O1—C11	1.205 (4)	C8—H8	0.9300
O2—C12	1.223 (3)	C9—C10	1.390 (4)
O3—C14	1.347 (3)	C9—C14	1.455 (5)
O3—C16	1.483 (4)	C10—C11	1.485 (4)
C1—C2	1.344 (4)	C11—C12	1.547 (5)
C1—C6	1.434 (4)	C12—C13	1.416 (4)
C1—C17	1.510 (4)	C13—C14	1.335 (4)
C2—C3	1.405 (4)	C13—C15	1.505 (4)
C2—H2	0.9300	C15—C18	1.510 (4)
C3—C4	1.360 (4)	C15—C16	1.533 (4)
C3—H3	0.9300	C15—H15	0.9800
C4—C5	1.410 (4)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C10	1.421 (4)	C17—H17A	0.9600
C5—C6	1.435 (4)	C17—H17B	0.9600
C6—C7	1.401 (4)	C17—H17C	0.9600
C7—C8	1.371 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.386 (4)	C18—H18C	0.9600
C14—O3—C16	107.0 (3)	O2—C12—C13	124.4 (4)
C2—C1—C6	118.9 (4)	O2—C12—C11	118.4 (3)
C2—C1—C17	121.2 (4)	C13—C12—C11	117.2 (4)
C6—C1—C17	119.8 (3)	C14—C13—C12	118.9 (4)
C1—C2—C3	121.2 (4)	C14—C13—C15	110.7 (3)
C1—C2—H2	119.4	C12—C13—C15	130.4 (4)
C3—C2—H2	119.4	C13—C14—O3	114.3 (4)
C4—C3—C2	121.7 (4)	C13—C14—C9	127.4 (4)
C4—C3—H3	119.2	O3—C14—C9	118.3 (4)
C2—C3—H3	119.2	C13—C15—C18	113.4 (3)
C3—C4—C5	120.2 (4)	C13—C15—C16	100.7 (3)
C3—C4—H4	119.9	C18—C15—C16	113.9 (3)
C5—C4—H4	119.9	C13—C15—H15	109.5
C4—C5—C10	123.4 (4)	C18—C15—H15	109.5
C4—C5—C6	117.9 (3)	C16—C15—H15	109.5
C10—C5—C6	118.8 (3)	O3—C16—C15	107.2 (3)
C7—C6—C1	121.0 (4)	O3—C16—H16A	110.3
C7—C6—C5	118.8 (3)	C15—C16—H16A	110.3
C1—C6—C5	120.2 (3)	O3—C16—H16B	110.3
C8—C7—C6	121.8 (4)	C15—C16—H16B	110.3
C8—C7—H7	119.1	H16A—C16—H16B	108.5
C6—C7—H7	119.1	C1—C17—H17A	109.5
C7—C8—C9	119.6 (4)	C1—C17—H17B	109.5
C7—C8—H8	120.2	H17A—C17—H17B	109.5
C9—C8—H8	120.2	C1—C17—H17C	109.5
C8—C9—C10	121.7 (4)	H17A—C17—H17C	109.5
C8—C9—C14	119.7 (4)	H17B—C17—H17C	109.5
C10—C9—C14	118.5 (4)	C15—C18—H18A	109.5
C9—C10—C5	119.3 (3)	C15—C18—H18B	109.5
C9—C10—C11	117.9 (4)	H18A—C18—H18B	109.5
C5—C10—C11	122.8 (3)	C15—C18—H18C	109.5
O1—C11—C10	124.2 (4)	H18A—C18—H18C	109.5
O1—C11—C12	116.1 (3)	H18B—C18—H18C	109.5
C10—C11—C12	119.7 (3)
C6—C1—C2—C3	−1.1 (6)	C5—C10—C11—O1	−4.4 (6)
C17—C1—C2—C3	179.9 (3)	C9—C10—C11—C12	−2.3 (5)
C1—C2—C3—C4	0.0 (6)	C5—C10—C11—C12	177.7 (3)
C2—C3—C4—C5	0.2 (6)	O1—C11—C12—O2	8.4 (5)
C3—C4—C5—C10	−179.7 (3)	C10—C11—C12—O2	−173.6 (3)
C3—C4—C5—C6	0.7 (5)	O1—C11—C12—C13	−171.5 (4)
C2—C1—C6—C7	−177.9 (4)	C10—C11—C12—C13	6.5 (5)
C17—C1—C6—C7	1.1 (5)	O2—C12—C13—C14	173.8 (4)
C2—C1—C6—C5	2.0 (5)	C11—C12—C13—C14	−6.4 (5)
C17—C1—C6—C5	−179.0 (3)	O2—C12—C13—C15	−6.3 (6)
C4—C5—C6—C7	178.1 (3)	C11—C12—C13—C15	173.6 (3)
C10—C5—C6—C7	−1.5 (4)	C12—C13—C14—O3	−179.6 (3)
C4—C5—C6—C1	−1.8 (5)	C15—C13—C14—O3	0.4 (4)
C10—C5—C6—C1	178.6 (3)	C12—C13—C14—C9	2.3 (6)
C1—C6—C7—C8	−179.9 (3)	C15—C13—C14—C9	−177.7 (3)
C5—C6—C7—C8	0.2 (5)	C16—O3—C14—C13	0.8 (4)
C6—C7—C8—C9	0.5 (6)	C16—O3—C14—C9	179.1 (3)
C7—C8—C9—C10	0.1 (5)	C8—C9—C14—C13	−178.3 (4)
C7—C8—C9—C14	−179.4 (3)	C10—C9—C14—C13	2.2 (6)
C8—C9—C10—C5	−1.3 (5)	C8—C9—C14—O3	3.7 (5)
C14—C9—C10—C5	178.1 (3)	C10—C9—C14—O3	−175.8 (3)
C8—C9—C10—C11	178.7 (3)	C14—C13—C15—C18	120.7 (3)
C14—C9—C10—C11	−1.9 (5)	C12—C13—C15—C18	−59.3 (5)
C4—C5—C10—C9	−177.5 (3)	C14—C13—C15—C16	−1.4 (4)
C6—C5—C10—C9	2.0 (4)	C12—C13—C15—C16	178.7 (4)
C4—C5—C10—C11	2.5 (5)	C14—O3—C16—C15	−1.7 (4)
C6—C5—C10—C11	−178.0 (3)	C13—C15—C16—O3	1.8 (4)
C9—C10—C11—O1	175.6 (4)	C18—C15—C16—O3	−120.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1i	0.96	2.53	3.379 (4)	147
C16—H16A···O2i	0.97	2.48	3.384 (5)	155
C17—H17A···O2ii	0.96	2.56	3.484 (4)	162
C17—H17C···O2iii	0.96	2.66	3.377 (4)	132
C7—H7···O3iv	0.93	2.67	3.481 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O1i	0.96	2.53	3.379 (4)	147
C16—H16A⋯O2i	0.97	2.48	3.384 (5)	155
C17—H17A⋯O2ii	0.96	2.56	3.484 (4)	162
C17—H17C⋯O2iii	0.96	2.66	3.377 (4)	132
C7—H7⋯O3iv	0.93	2.67	3.481 (4)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .