Tricyclo-[6.2.1.0]undeca-4,9-diene-3,6-dione.

The title compound, C(11)H(10)O(2), crystallizes with two independent mol-ecules in the asymmetric unit. In one mol-ecule, the dihedral angle between the mean planes of the C-C=C-C group of the diene unit and essentially planar cyclo-hexene ring is 51.07 (9)°, while in the other mol-ecule it is 54.49 (12)°. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into columns along the b axis.

Related literature

For background information, see: Ito et al. (2007 ▶); Mgani et al. (1995 ▶).

Experimental

Crystal data

C11H10O2

M = 174.19

Monoclinic,

a = 15.649 (3) Å

b = 6.5399 (13) Å

c = 21.448 (7) Å

β = 125.05 (2)°

V = 1797.0 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.52 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.990

6936 measured reflections

4119 independent reflections

2664 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.210

S = 1.03

4119 reflections

251 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030249/lh2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030249/lh2695Isup2.hkl

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

C11H10O2	F(000) = 736
Mr = 174.19	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16732 reflections
a = 15.649 (3) Å	θ = 1.6–27.5°
b = 6.5399 (13) Å	µ = 0.09 mm−1
c = 21.448 (7) Å	T = 293 K
β = 125.05 (2)°	Needle, dark brown
V = 1797.0 (8) Å3	0.52 × 0.12 × 0.11 mm
Z = 8

Rigaku R-AXIS RAPID IP area-detector diffractometer	4119 independent reflections
Radiation source: Rotating Anode	2664 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω oscillation scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.956, Tmax = 0.990	k = −8→8
6936 measured reflections	l = −27→27

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.118P)2 + 0.1983P] where P = (Fo2 + 2Fc2)/3
4119 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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	0.29192 (15)	0.0348 (3)	0.02418 (12)	0.0946 (7)
O2	0.1016 (2)	−0.5875 (3)	−0.16845 (10)	0.1029 (8)
C1	0.23966 (16)	−0.1048 (3)	−0.01874 (12)	0.0551 (5)
C2	0.28081 (17)	−0.3137 (4)	−0.00061 (13)	0.0596 (6)
H2A	0.3425	−0.3397	0.0467	0.074 (7)*
C3	0.23343 (19)	−0.4665 (4)	−0.04914 (13)	0.0616 (6)
H3A	0.2631	−0.5960	−0.0342	0.080 (8)*
C4	0.13635 (19)	−0.4419 (4)	−0.12469 (12)	0.0581 (6)
C5	0.07944 (16)	−0.2423 (3)	−0.14694 (10)	0.0490 (5)
H5A	0.0655	−0.1990	−0.1957	0.067 (7)*
C6	0.13399 (15)	−0.0649 (3)	−0.08969 (11)	0.0478 (5)
H6A	0.1391	0.0514	−0.1162	0.066 (7)*
C7	0.05338 (18)	−0.0092 (4)	−0.07124 (13)	0.0638 (7)
H7A	0.0633	0.1236	−0.0468	0.082 (8)*
C8	−0.04733 (19)	−0.0353 (5)	−0.15063 (15)	0.0781 (8)
H8A	−0.1095	−0.0148	−0.1516	0.111 (11)*
H8B	−0.0497	0.0498	−0.1886	0.082 (8)*
C9	−0.02716 (19)	−0.2589 (5)	−0.15655 (14)	0.0706 (7)
H9A	−0.0828	−0.3311	−0.2022	0.096 (9)*
C10	−0.0019 (2)	−0.3395 (5)	−0.08217 (17)	0.0799 (8)
H10A	−0.0175	−0.4691	−0.0735	0.096*
C11	0.0467 (2)	−0.1914 (5)	−0.03133 (15)	0.0760 (8)
H11A	0.0721	−0.1986	0.0199	0.091*
O3	0.2497 (2)	−0.2686 (4)	−0.34967 (12)	0.1181 (10)
O4	0.48892 (15)	0.3614 (3)	−0.18269 (12)	0.0870 (6)
C12	0.3043 (2)	−0.1294 (4)	−0.30817 (13)	0.0652 (6)
C13	0.28648 (19)	0.0779 (4)	−0.33792 (13)	0.0656 (6)
H13A	0.2323	0.1012	−0.3886	0.092 (9)*
C14	0.34485 (18)	0.2354 (4)	−0.29597 (14)	0.0620 (6)
H14A	0.3289	0.3645	−0.3182	0.082 (9)*
C15	0.43306 (16)	0.2141 (3)	−0.21624 (13)	0.0541 (5)
C16	0.45436 (15)	0.0118 (3)	−0.17730 (11)	0.0504 (5)
H16A	0.5278	−0.0221	−0.1540	0.050 (6)*
C17	0.38776 (16)	−0.1714 (3)	−0.22614 (11)	0.0511 (5)
H17A	0.4348	−0.2753	−0.2236	0.066 (7)*
C18	0.34259 (19)	−0.2549 (4)	−0.18255 (14)	0.0665 (7)
H18A	0.3164	−0.3956	−0.1948	0.070 (7)*
C19	0.4353 (2)	−0.2168 (5)	−0.10083 (14)	0.0796 (8)
H19A	0.4984	−0.2847	−0.0886	0.083 (9)*
H19B	0.4212	−0.2508	−0.0636	0.129 (13)*
C20	0.4363 (2)	0.0123 (5)	−0.11275 (13)	0.0755 (8)
H20A	0.4863	0.0923	−0.0673	0.085 (8)*
C21	0.3220 (3)	0.0601 (6)	−0.15010 (19)	0.0928 (10)
H21A	0.2952	0.1807	−0.1449	0.111*
C22	0.2675 (2)	−0.0992 (5)	−0.19120 (19)	0.0837 (9)
H22A	0.1953	−0.1120	−0.2203	0.100*

	U11	U22	U33	U12	U13	U23
O1	0.0699 (12)	0.0600 (11)	0.0883 (13)	−0.0093 (9)	0.0071 (10)	−0.0161 (10)
O2	0.152 (2)	0.0603 (12)	0.0557 (11)	0.0017 (12)	0.0360 (12)	−0.0137 (9)
C1	0.0451 (11)	0.0487 (12)	0.0563 (12)	−0.0051 (9)	0.0203 (10)	−0.0048 (10)
C2	0.0436 (11)	0.0587 (14)	0.0559 (12)	0.0071 (10)	0.0165 (10)	0.0076 (11)
C3	0.0689 (14)	0.0461 (13)	0.0621 (13)	0.0107 (10)	0.0332 (12)	0.0048 (10)
C4	0.0789 (15)	0.0498 (13)	0.0433 (10)	−0.0029 (10)	0.0337 (11)	−0.0023 (9)
C5	0.0531 (11)	0.0533 (12)	0.0338 (9)	−0.0004 (9)	0.0210 (8)	0.0037 (8)
C6	0.0473 (11)	0.0420 (11)	0.0495 (10)	0.0025 (8)	0.0252 (9)	0.0044 (9)
C7	0.0566 (13)	0.0709 (16)	0.0573 (12)	0.0184 (11)	0.0290 (11)	−0.0016 (11)
C8	0.0511 (14)	0.107 (2)	0.0661 (15)	0.0232 (14)	0.0278 (12)	0.0209 (15)
C9	0.0462 (12)	0.091 (2)	0.0531 (12)	−0.0129 (12)	0.0158 (10)	0.0009 (13)
C10	0.0608 (15)	0.099 (2)	0.0882 (19)	−0.0061 (14)	0.0478 (15)	0.0189 (17)
C11	0.0644 (15)	0.116 (2)	0.0589 (14)	0.0220 (15)	0.0421 (13)	0.0195 (15)
O3	0.140 (2)	0.0854 (15)	0.0597 (11)	−0.0461 (14)	0.0168 (12)	−0.0131 (10)
O4	0.0699 (11)	0.0565 (11)	0.0983 (14)	−0.0123 (9)	0.0271 (10)	−0.0112 (10)
C12	0.0673 (14)	0.0638 (16)	0.0458 (11)	−0.0136 (11)	0.0216 (11)	−0.0050 (10)
C13	0.0593 (13)	0.0700 (16)	0.0463 (12)	0.0002 (11)	0.0179 (10)	0.0078 (11)
C14	0.0592 (13)	0.0550 (14)	0.0658 (13)	0.0049 (10)	0.0323 (12)	0.0107 (11)
C15	0.0439 (11)	0.0511 (13)	0.0637 (13)	−0.0030 (9)	0.0288 (10)	−0.0090 (10)
C16	0.0380 (10)	0.0581 (13)	0.0476 (10)	0.0017 (8)	0.0201 (9)	−0.0036 (9)
C17	0.0529 (11)	0.0498 (12)	0.0485 (11)	0.0011 (9)	0.0279 (9)	−0.0009 (9)
C18	0.0641 (14)	0.0672 (16)	0.0671 (14)	−0.0060 (12)	0.0370 (12)	0.0097 (12)
C19	0.0854 (19)	0.099 (2)	0.0553 (14)	0.0059 (16)	0.0409 (14)	0.0162 (14)
C20	0.0889 (19)	0.089 (2)	0.0512 (13)	−0.0114 (15)	0.0418 (13)	−0.0153 (13)
C21	0.123 (3)	0.095 (2)	0.113 (2)	0.024 (2)	0.098 (2)	0.005 (2)
C22	0.0706 (17)	0.098 (2)	0.104 (2)	0.0038 (16)	0.0628 (17)	0.0162 (19)

O1—C1	1.219 (3)	O3—C12	1.215 (3)
O2—C4	1.224 (3)	O4—C15	1.220 (3)
C1—C2	1.464 (3)	C12—C13	1.456 (4)
C1—C6	1.493 (3)	C12—C17	1.496 (3)
C2—C3	1.321 (3)	C13—C14	1.327 (3)
C2—H2A	0.9301	C13—H13A	0.9300
C3—C4	1.460 (3)	C14—C15	1.462 (3)
C3—H3A	0.9299	C14—H14A	0.9300
C4—C5	1.495 (3)	C15—C16	1.497 (3)
C5—C6	1.542 (3)	C16—C17	1.538 (3)
C5—C9	1.563 (3)	C16—C20	1.564 (3)
C5—H5A	0.9799	C16—H16A	0.9800
C6—C7	1.567 (3)	C17—C18	1.559 (3)
C6—H6A	0.9800	C17—H17A	0.9800
C7—C11	1.505 (4)	C18—C22	1.483 (4)
C7—C8	1.526 (3)	C18—C19	1.523 (4)
C7—H7A	0.9800	C18—H18A	0.9800
C8—C9	1.517 (4)	C19—C20	1.522 (4)
C8—H8A	0.9702	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.502 (4)	C20—C21	1.514 (4)
C9—H9A	0.9801	C20—H20A	0.9801
C10—C11	1.324 (4)	C21—C22	1.314 (4)
C10—H10A	0.9300	C21—H21A	0.9300
C11—H11A	0.9300	C22—H22A	0.9300
O1—C1—C2	119.8 (2)	O3—C12—C13	120.0 (2)
O1—C1—C6	120.6 (2)	O3—C12—C17	119.7 (2)
C2—C1—C6	119.63 (18)	C13—C12—C17	120.3 (2)
C3—C2—C1	122.3 (2)	C14—C13—C12	122.8 (2)
C3—C2—H2A	118.8	C14—C13—H13A	118.4
C1—C2—H2A	118.9	C12—C13—H13A	118.8
C2—C3—C4	123.1 (2)	C13—C14—C15	122.6 (2)
C2—C3—H3A	118.3	C13—C14—H14A	118.7
C4—C3—H3A	118.6	C15—C14—H14A	118.7
O2—C4—C3	119.1 (2)	O4—C15—C14	119.4 (2)
O2—C4—C5	120.9 (2)	O4—C15—C16	121.0 (2)
C3—C4—C5	120.00 (19)	C14—C15—C16	119.67 (19)
C4—C5—C6	116.52 (17)	C15—C16—C17	117.52 (17)
C4—C5—C9	112.11 (19)	C15—C16—C20	113.36 (19)
C6—C5—C9	102.60 (18)	C17—C16—C20	102.03 (18)
C4—C5—H5A	108.6	C15—C16—H16A	107.7
C6—C5—H5A	108.3	C17—C16—H16A	108.0
C9—C5—H5A	108.3	C20—C16—H16A	107.8
C1—C6—C5	117.58 (17)	C12—C17—C16	116.78 (19)
C1—C6—C7	111.38 (18)	C12—C17—C18	112.29 (19)
C5—C6—C7	102.61 (17)	C16—C17—C18	103.15 (17)
C1—C6—H6A	108.4	C12—C17—H17A	108.2
C5—C6—H6A	108.3	C16—C17—H17A	108.0
C7—C6—H6A	108.1	C18—C17—H17A	108.0
C11—C7—C8	100.5 (2)	C22—C18—C19	101.2 (2)
C11—C7—C6	106.78 (19)	C22—C18—C17	106.5 (2)
C8—C7—C6	99.07 (18)	C19—C18—C17	99.93 (19)
C11—C7—H7A	116.0	C22—C18—H18A	115.5
C8—C7—H7A	116.2	C19—C18—H18A	115.9
C6—C7—H7A	116.0	C17—C18—H18A	115.6
C9—C8—C7	94.01 (19)	C20—C19—C18	93.6 (2)
C9—C8—H8A	112.7	C20—C19—H19A	112.9
C7—C8—H8A	112.9	C18—C19—H19A	112.7
C9—C8—H8B	113.1	C20—C19—H19B	113.1
C7—C8—H8B	112.9	C18—C19—H19B	113.2
H8A—C8—H8B	110.4	H19A—C19—H19B	110.5
C10—C9—C8	100.9 (2)	C21—C20—C19	99.8 (3)
C10—C9—C5	105.94 (19)	C21—C20—C16	106.9 (2)
C8—C9—C5	100.4 (2)	C19—C20—C16	99.8 (2)
C10—C9—H9A	115.7	C21—C20—H20A	116.2
C8—C9—H9A	116.1	C19—C20—H20A	116.0
C5—C9—H9A	115.7	C16—C20—H20A	115.8
C11—C10—C9	107.1 (3)	C22—C21—C20	107.8 (3)
C11—C10—H10A	126.4	C22—C21—H21A	126.1
C9—C10—H10A	126.4	C20—C21—H21A	126.1
C10—C11—C7	107.8 (2)	C21—C22—C18	107.4 (3)
C10—C11—H11A	126.1	C21—C22—H22A	126.3
C7—C11—H11A	126.1	C18—C22—H22A	126.3
O1—C1—C2—C3	−171.7 (3)	O3—C12—C13—C14	−178.5 (3)
C6—C1—C2—C3	8.3 (4)	C17—C12—C13—C14	3.1 (4)
C1—C2—C3—C4	−0.1 (4)	C12—C13—C14—C15	0.7 (4)
C2—C3—C4—O2	174.5 (3)	C13—C14—C15—O4	173.9 (3)
C2—C3—C4—C5	−7.1 (4)	C13—C14—C15—C16	−5.3 (4)
O2—C4—C5—C6	−175.9 (2)	O4—C15—C16—C17	−173.3 (2)
C3—C4—C5—C6	5.7 (3)	C14—C15—C16—C17	5.9 (3)
O2—C4—C5—C9	66.3 (3)	O4—C15—C16—C20	68.0 (3)
C3—C4—C5—C9	−112.1 (2)	C14—C15—C16—C20	−112.8 (2)
O1—C1—C6—C5	171.2 (2)	O3—C12—C17—C16	179.5 (3)
C2—C1—C6—C5	−8.9 (3)	C13—C12—C17—C16	−2.1 (3)
O1—C1—C6—C7	−70.9 (3)	O3—C12—C17—C18	−61.7 (3)
C2—C1—C6—C7	109.1 (2)	C13—C12—C17—C18	116.7 (3)
C4—C5—C6—C1	2.1 (3)	C15—C16—C17—C12	−2.3 (3)
C9—C5—C6—C1	124.9 (2)	C20—C16—C17—C12	122.3 (2)
C4—C5—C6—C7	−120.51 (19)	C15—C16—C17—C18	−125.9 (2)
C9—C5—C6—C7	2.3 (2)	C20—C16—C17—C18	−1.3 (2)
C1—C6—C7—C11	−61.5 (2)	C12—C17—C18—C22	−57.7 (3)
C5—C6—C7—C11	65.1 (2)	C16—C17—C18—C22	68.9 (2)
C1—C6—C7—C8	−165.4 (2)	C12—C17—C18—C19	−162.6 (2)
C5—C6—C7—C8	−38.8 (2)	C16—C17—C18—C19	−36.0 (2)
C11—C7—C8—C9	−49.1 (2)	C22—C18—C19—C20	−50.3 (2)
C6—C7—C8—C9	60.0 (2)	C17—C18—C19—C20	58.9 (2)
C7—C8—C9—C10	49.8 (2)	C18—C19—C20—C21	49.3 (2)
C7—C8—C9—C5	−58.9 (2)	C18—C19—C20—C16	−59.9 (2)
C4—C5—C9—C10	56.3 (3)	C15—C16—C20—C21	62.2 (3)
C6—C5—C9—C10	−69.4 (3)	C17—C16—C20—C21	−65.2 (3)
C4—C5—C9—C8	160.98 (18)	C15—C16—C20—C19	165.6 (2)
C6—C5—C9—C8	35.2 (2)	C17—C16—C20—C19	38.3 (2)
C8—C9—C10—C11	−33.6 (3)	C19—C20—C21—C22	−33.2 (3)
C5—C9—C10—C11	70.6 (3)	C16—C20—C21—C22	70.3 (3)
C9—C10—C11—C7	0.7 (3)	C20—C21—C22—C18	0.0 (3)
C8—C7—C11—C10	32.2 (3)	C19—C18—C22—C21	33.3 (3)
C6—C7—C11—C10	−70.7 (3)	C17—C18—C22—C21	−70.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.93	2.58	3.502 (3)	172
C6—H6A···O2ii	0.98	2.53	3.446 (3)	155
C11—H11A···O3iii	0.93	2.58	3.335 (4)	138
C16—H16A···O1i	0.98	2.59	3.416 (3)	142
C17—H17A···O4iv	0.98	2.51	3.319 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.93	2.58	3.502 (3)	172
C6—H6A⋯O2ii	0.98	2.53	3.446 (3)	155
C11—H11A⋯O3iii	0.93	2.58	3.335 (4)	138
C16—H16A⋯O1i	0.98	2.59	3.416 (3)	142
C17—H17A⋯O4iv	0.98	2.51	3.319 (3)	140

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