5-(1H-Inden-2-yl)-1,3-benzodioxole.

In the title compound, C(16)H(12)O(2), the non-H atoms are coplanar with a mean r.m.s. deviation of 0.0260 (2) Å. The deviations of the bond angles from normal values at the indenyl junction C atom and the indenyl bridgehead C atom nearest the junction are imposed by the five-membered ring geometry. Due to conjugation, the single bond linking the two ring systems [1.455 (3) Å] is significantly shorter than the formal single bonds in the five-membered carbocyclic ring [1.500 (3) and 1.489 (3) Å].

Related literature

For related literature, see: Rayabarapu et al. (2003 ▶); Senanayake et al. (1995 ▶).

Experimental

Crystal data

C16H12O2

M = 236.26

Orthorhombic,

a = 22.277 (10) Å

b = 6.892 (3) Å

c = 7.580 (3) Å

V = 1163.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.24 × 0.22 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.990

6325 measured reflections

1286 independent reflections

1072 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.08

1286 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 global, I. DOI: 10.1107/S1600536808001578/kp2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001578/kp2152Isup2.hkl

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

C16H12O2	F000 = 496
Mr = 236.26	Dx = 1.348 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2528 reflections
a = 22.277 (10) Å	θ = 2.7–25.2º
b = 6.892 (3) Å	µ = 0.09 mm−1
c = 7.580 (3) Å	T = 294 (2) K
V = 1163.7 (9) Å3	Plate, colourless
Z = 4	0.24 × 0.22 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	1286 independent reflections
Radiation source: fine-focus sealed tube	1072 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 294(2) K	θmax = 26.4º
φ and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −27→13
Tmin = 0.979, Tmax = 0.990	k = −8→8
6325 measured reflections	l = −8→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.0272P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.12 e Å−3
1286 reflections	Δρmin = −0.11 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.006 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: indeterminate
Secondary atom site location: difference Fourier map

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	0.33678 (7)	0.3967 (2)	0.9508 (3)	0.0629 (5)
O2	0.41993 (8)	0.2623 (2)	1.0832 (3)	0.0676 (6)
C1	0.35772 (11)	0.2393 (4)	1.0539 (5)	0.0686 (8)
H1A	0.3366	0.2362	1.1658	0.082*
H1B	0.3502	0.1180	0.9929	0.082*
C2	0.38388 (9)	0.5252 (3)	0.9457 (3)	0.0472 (5)
C3	0.38568 (10)	0.7034 (3)	0.8718 (4)	0.0512 (6)
H3	0.3523	0.7568	0.8162	0.061*
C4	0.43988 (10)	0.8035 (3)	0.8829 (3)	0.0480 (5)
H4	0.4425	0.9262	0.8326	0.058*
C5	0.49008 (9)	0.7272 (3)	0.9662 (3)	0.0415 (5)
C6	0.48641 (10)	0.5410 (3)	1.0401 (3)	0.0468 (5)
H6	0.5192	0.4849	1.0966	0.056*
C7	0.43337 (10)	0.4460 (3)	1.0263 (3)	0.0472 (5)
C8	0.54537 (9)	0.8392 (3)	0.9756 (3)	0.0417 (5)
C9	0.55116 (10)	1.0396 (3)	0.9004 (3)	0.0482 (5)
H9A	0.5435	1.0394	0.7744	0.058*
H9B	0.5234	1.1284	0.9570	0.058*
C10	0.61447 (10)	1.0948 (3)	0.9384 (3)	0.0488 (6)
C11	0.64540 (11)	1.2630 (4)	0.9035 (4)	0.0606 (7)
H11	0.6271	1.3649	0.8438	0.073*
C12	0.70444 (12)	1.2778 (4)	0.9592 (4)	0.0703 (8)
H12	0.7259	1.3910	0.9372	0.084*
C13	0.73163 (11)	1.1275 (4)	1.0462 (4)	0.0692 (8)
H13	0.7714	1.1399	1.0822	0.083*
C14	0.70099 (10)	0.9578 (4)	1.0814 (4)	0.0611 (7)
H14	0.7198	0.8564	1.1405	0.073*
C15	0.64208 (10)	0.9406 (3)	1.0277 (3)	0.0489 (6)
C16	0.59838 (10)	0.7872 (3)	1.0480 (3)	0.0483 (5)
H16	0.6057	0.6691	1.1032	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0482 (8)	0.0638 (10)	0.0767 (12)	−0.0047 (7)	−0.0055 (9)	0.0074 (10)
O2	0.0584 (10)	0.0524 (10)	0.0920 (15)	−0.0043 (8)	−0.0100 (10)	0.0205 (10)
C1	0.0586 (15)	0.0618 (15)	0.085 (2)	−0.0056 (12)	−0.0049 (15)	0.0124 (16)
C2	0.0460 (12)	0.0512 (12)	0.0443 (12)	0.0027 (9)	−0.0027 (11)	−0.0031 (11)
C3	0.0485 (13)	0.0532 (12)	0.0519 (13)	0.0110 (10)	−0.0098 (11)	0.0034 (12)
C4	0.0531 (13)	0.0433 (11)	0.0477 (12)	0.0069 (10)	−0.0060 (11)	0.0016 (10)
C5	0.0479 (12)	0.0410 (10)	0.0357 (10)	0.0080 (8)	−0.0030 (10)	−0.0034 (9)
C6	0.0482 (12)	0.0446 (12)	0.0476 (12)	0.0082 (9)	−0.0083 (10)	0.0005 (11)
C7	0.0523 (12)	0.0428 (11)	0.0466 (12)	0.0080 (10)	−0.0005 (11)	−0.0005 (10)
C8	0.0470 (11)	0.0414 (10)	0.0365 (10)	0.0086 (9)	−0.0040 (9)	−0.0039 (9)
C9	0.0536 (12)	0.0425 (11)	0.0485 (13)	0.0069 (10)	−0.0049 (11)	−0.0001 (10)
C10	0.0521 (13)	0.0539 (12)	0.0404 (12)	0.0021 (10)	0.0062 (10)	−0.0082 (11)
C11	0.0640 (16)	0.0615 (15)	0.0564 (15)	−0.0072 (12)	0.0080 (13)	−0.0007 (12)
C12	0.0664 (17)	0.0803 (18)	0.0644 (16)	−0.0188 (13)	0.0157 (16)	−0.0118 (16)
C13	0.0431 (13)	0.094 (2)	0.0701 (18)	−0.0063 (13)	0.0081 (14)	−0.0234 (17)
C14	0.0461 (14)	0.0761 (18)	0.0612 (16)	0.0082 (12)	0.0014 (12)	−0.0127 (13)
C15	0.0450 (12)	0.0569 (13)	0.0450 (12)	0.0079 (10)	0.0026 (11)	−0.0102 (11)
C16	0.0517 (12)	0.0459 (11)	0.0473 (12)	0.0076 (10)	−0.0047 (11)	−0.0022 (11)

O1—C2	1.374 (3)	C8—C9	1.500 (3)
O1—C1	1.416 (3)	C9—C10	1.489 (3)
O2—C7	1.370 (3)	C9—H9A	0.9700
O2—C1	1.412 (3)	C9—H9B	0.9700
C1—H1A	0.9700	C10—C11	1.375 (3)
C1—H1B	0.9700	C10—C15	1.402 (3)
C2—C3	1.351 (3)	C11—C12	1.385 (4)
C2—C7	1.373 (3)	C11—H11	0.9300
C3—C4	1.393 (3)	C12—C13	1.369 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.387 (3)	C13—C14	1.380 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.402 (3)	C14—C15	1.379 (3)
C5—C8	1.455 (3)	C14—H14	0.9300
C6—C7	1.355 (3)	C15—C16	1.446 (3)
C6—H6	0.9300	C16—H16	0.9300
C8—C16	1.350 (3)
C2—O1—C1	104.93 (18)	C5—C8—C9	122.86 (17)
C7—O2—C1	105.56 (18)	C10—C9—C8	104.06 (17)
O2—C1—O1	108.9 (2)	C10—C9—H9A	110.9
O2—C1—H1A	109.9	C8—C9—H9A	110.9
O1—C1—H1A	109.9	C10—C9—H9B	110.9
O2—C1—H1B	109.9	C8—C9—H9B	110.9
O1—C1—H1B	109.9	H9A—C9—H9B	109.0
H1A—C1—H1B	108.3	C11—C10—C15	120.8 (2)
C3—C2—C7	121.5 (2)	C11—C10—C9	130.8 (2)
C3—C2—O1	128.4 (2)	C15—C10—C9	108.4 (2)
C7—C2—O1	110.1 (2)	C10—C11—C12	118.6 (3)
C2—C3—C4	116.8 (2)	C10—C11—H11	120.7
C2—C3—H3	121.6	C12—C11—H11	120.7
C4—C3—H3	121.6	C13—C12—C11	120.8 (3)
C5—C4—C3	122.6 (2)	C13—C12—H12	119.6
C5—C4—H4	118.7	C11—C12—H12	119.6
C3—C4—H4	118.7	C12—C13—C14	121.0 (2)
C4—C5—C6	118.8 (2)	C12—C13—H13	119.5
C4—C5—C8	120.23 (19)	C14—C13—H13	119.5
C6—C5—C8	120.99 (18)	C15—C14—C13	119.1 (3)
C7—C6—C5	117.51 (19)	C15—C14—H14	120.4
C7—C6—H6	121.2	C13—C14—H14	120.4
C5—C6—H6	121.2	C14—C15—C10	119.7 (2)
C6—C7—O2	127.8 (2)	C14—C15—C16	132.2 (2)
C6—C7—C2	122.8 (2)	C10—C15—C16	108.1 (2)
O2—C7—C2	109.38 (19)	C8—C16—C15	110.6 (2)
C16—C8—C5	128.3 (2)	C8—C16—H16	124.7
C16—C8—C9	108.88 (19)	C15—C16—H16	124.7
C7—O2—C1—O1	10.4 (3)	C4—C5—C8—C9	0.9 (3)
C2—O1—C1—O2	−9.7 (3)	C6—C5—C8—C9	−179.3 (2)
C1—O1—C2—C3	−176.1 (3)	C16—C8—C9—C10	0.3 (2)
C1—O1—C2—C7	5.4 (3)	C5—C8—C9—C10	−179.4 (2)
C7—C2—C3—C4	−0.7 (3)	C8—C9—C10—C11	−178.7 (2)
O1—C2—C3—C4	−179.0 (2)	C8—C9—C10—C15	−0.2 (2)
C2—C3—C4—C5	−0.4 (4)	C15—C10—C11—C12	−0.3 (4)
C3—C4—C5—C6	0.9 (4)	C9—C10—C11—C12	178.0 (3)
C3—C4—C5—C8	−179.3 (2)	C10—C11—C12—C13	0.4 (4)
C4—C5—C6—C7	−0.3 (3)	C11—C12—C13—C14	−0.2 (4)
C8—C5—C6—C7	179.9 (2)	C12—C13—C14—C15	−0.1 (4)
C5—C6—C7—O2	177.9 (2)	C13—C14—C15—C10	0.1 (4)
C5—C6—C7—C2	−0.8 (4)	C13—C14—C15—C16	−178.2 (3)
C1—O2—C7—C6	174.2 (3)	C11—C10—C15—C14	0.1 (3)
C1—O2—C7—C2	−7.0 (3)	C9—C10—C15—C14	−178.6 (2)
C3—C2—C7—C6	1.3 (4)	C11—C10—C15—C16	178.8 (2)
O1—C2—C7—C6	179.9 (2)	C9—C10—C15—C16	0.1 (3)
C3—C2—C7—O2	−177.6 (2)	C5—C8—C16—C15	179.4 (2)
O1—C2—C7—O2	1.0 (3)	C9—C8—C16—C15	−0.2 (3)
C4—C5—C8—C16	−178.7 (2)	C14—C15—C16—C8	178.6 (2)
C6—C5—C8—C16	1.1 (4)	C10—C15—C16—C8	0.1 (3)