Bicyclo-[2.2.2]oct-7-ene-2,3,5,6-tetra-carboxylic dianhydride.

In the title compound, C(12)H(8)O(6), mol-ecules are linked by weak C-H⋯O inter-actions involving all the potential donors, generating a three-dimensional network.

Experimental

Crystal data

C12H8O6

M = 248.18

Monoclinic,

a = 7.627 (2) Å

b = 13.877 (3) Å

c = 9.823 (2) Å

β = 100.68 (2)°

V = 1021.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 (2) K

0.28 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.921, T max = 0.987

11412 measured reflections

2119 independent reflections

1460 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.01

2118 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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/S1600536808012452/sg2233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012452/sg2233Isup2.hkl

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

C12H8O6	F000 = 512
Mr = 248.18	Dx = 1.613 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2677 reflections
a = 7.627 (2) Å	θ = 2.9–24.1º
b = 13.877 (3) Å	µ = 0.13 mm−1
c = 9.823 (2) Å	T = 296 (2) K
β = 100.68 (2)º	Prism, colourless
V = 1021.7 (4) Å3	0.28 × 0.16 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2119 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.051
T = 296(2) K	θmax = 26.5º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.921, Tmax = 0.987	k = −17→15
11412 measured reflections	l = −11→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0334P)2 + 0.3914P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.21 e Å−3
2118 reflections	Δρmin = −0.16 e Å−3
164 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.005 (1)
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
C1	0.7820 (3)	0.83700 (16)	0.6304 (2)	0.0449 (5)
C2	0.5829 (2)	0.84372 (13)	0.61717 (19)	0.0355 (4)
H2	0.5239	0.8381	0.5200	0.043*
C3	0.5305 (2)	0.93909 (13)	0.68048 (19)	0.0350 (4)
H3	0.5646	0.9952	0.6307	0.042*
C4	0.3256 (2)	0.93415 (13)	0.67248 (18)	0.0344 (4)
H4	0.2633	0.9301	0.5760	0.041*
C5	0.2627 (3)	1.01999 (15)	0.7435 (2)	0.0416 (5)
C6	0.1858 (3)	0.89126 (15)	0.8635 (2)	0.0434 (5)
C7	0.2788 (2)	0.84782 (13)	0.75613 (18)	0.0352 (4)
H7	0.1984	0.8039	0.6962	0.042*
C8	0.4506 (2)	0.79445 (13)	0.82409 (18)	0.0354 (4)
H8	0.4251	0.7413	0.8831	0.042*
C9	0.5347 (2)	0.75817 (13)	0.70190 (19)	0.0358 (4)
H9	0.4526	0.7145	0.6429	0.043*
C10	0.7097 (3)	0.70890 (16)	0.7535 (2)	0.0462 (5)
C11	0.5767 (2)	0.86683 (14)	0.90425 (19)	0.0392 (5)
H11	0.6221	0.8602	0.9984	0.047*
C12	0.6180 (2)	0.94061 (14)	0.83043 (19)	0.0394 (5)
H12	0.6951	0.9895	0.8686	0.047*
O1	0.88296 (19)	0.89053 (13)	0.58906 (17)	0.0638 (5)
O2	0.7409 (2)	0.64134 (12)	0.82843 (18)	0.0681 (5)
O3	0.2829 (2)	1.10382 (11)	0.72476 (16)	0.0596 (4)
O4	0.1289 (2)	0.85316 (12)	0.95463 (16)	0.0629 (5)
O5	0.84589 (17)	0.75576 (11)	0.70513 (15)	0.0537 (4)
O6	0.17498 (18)	0.99043 (10)	0.84767 (14)	0.0485 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0359 (11)	0.0528 (13)	0.0462 (12)	0.0033 (10)	0.0079 (9)	−0.0067 (10)
C2	0.0311 (9)	0.0378 (11)	0.0373 (10)	0.0016 (8)	0.0054 (7)	−0.0023 (8)
C3	0.0334 (9)	0.0298 (10)	0.0422 (10)	−0.0030 (8)	0.0076 (8)	0.0016 (8)
C4	0.0337 (9)	0.0331 (10)	0.0351 (9)	0.0039 (8)	0.0031 (7)	−0.0014 (8)
C5	0.0405 (11)	0.0389 (12)	0.0429 (11)	0.0098 (9)	0.0018 (9)	−0.0003 (9)
C6	0.0355 (10)	0.0470 (13)	0.0482 (12)	0.0008 (9)	0.0089 (9)	−0.0024 (10)
C7	0.0313 (9)	0.0327 (11)	0.0411 (10)	−0.0025 (8)	0.0052 (8)	−0.0035 (8)
C8	0.0375 (10)	0.0297 (10)	0.0390 (10)	0.0002 (8)	0.0070 (8)	0.0033 (8)
C9	0.0328 (9)	0.0309 (10)	0.0423 (10)	0.0017 (8)	0.0033 (8)	−0.0024 (8)
C10	0.0455 (12)	0.0419 (13)	0.0490 (12)	0.0112 (10)	0.0031 (9)	−0.0021 (10)
C11	0.0386 (10)	0.0415 (11)	0.0353 (10)	0.0047 (9)	0.0013 (8)	−0.0021 (9)
C12	0.0349 (10)	0.0369 (11)	0.0448 (11)	−0.0035 (8)	0.0034 (8)	−0.0078 (9)
O1	0.0392 (8)	0.0791 (12)	0.0768 (11)	−0.0069 (8)	0.0205 (8)	0.0052 (9)
O2	0.0689 (11)	0.0550 (10)	0.0784 (11)	0.0261 (8)	0.0083 (9)	0.0170 (9)
O3	0.0726 (11)	0.0345 (9)	0.0716 (11)	0.0137 (7)	0.0131 (8)	0.0022 (8)
O4	0.0655 (10)	0.0696 (11)	0.0616 (10)	−0.0019 (8)	0.0328 (8)	0.0038 (8)
O5	0.0326 (7)	0.0582 (10)	0.0685 (10)	0.0107 (7)	0.0044 (7)	0.0018 (8)
O6	0.0500 (8)	0.0464 (9)	0.0516 (8)	0.0096 (6)	0.0161 (7)	−0.0056 (7)

C1—O1	1.194 (2)	C6—O6	1.386 (2)
C1—O5	1.384 (2)	C6—C7	1.502 (3)
C1—C2	1.503 (3)	C7—C8	1.545 (2)
C2—C9	1.533 (3)	C7—H7	0.9800
C2—C3	1.546 (3)	C8—C11	1.508 (3)
C2—H2	0.9800	C8—C9	1.546 (3)
C3—C12	1.500 (3)	C8—H8	0.9800
C3—C4	1.551 (2)	C9—C10	1.502 (3)
C3—H3	0.9800	C9—H9	0.9800
C4—C5	1.504 (3)	C10—O2	1.188 (2)
C4—C7	1.532 (3)	C10—O5	1.382 (3)
C4—H4	0.9800	C11—C12	1.326 (3)
C5—O3	1.192 (2)	C11—H11	0.9300
C5—O6	1.384 (2)	C12—H12	0.9300
C6—O4	1.189 (2)
O1—C1—O5	120.12 (18)	C6—C7—C8	111.21 (15)
O1—C1—C2	129.6 (2)	C4—C7—C8	110.07 (15)
O5—C1—C2	110.29 (18)	C6—C7—H7	110.3
C1—C2—C9	104.20 (15)	C4—C7—H7	110.3
C1—C2—C3	110.54 (15)	C8—C7—H7	110.3
C9—C2—C3	109.79 (15)	C11—C8—C7	108.31 (15)
C1—C2—H2	110.7	C11—C8—C9	107.83 (15)
C9—C2—H2	110.7	C7—C8—C9	105.15 (14)
C3—C2—H2	110.7	C11—C8—H8	111.7
C12—C3—C2	107.81 (15)	C7—C8—H8	111.7
C12—C3—C4	108.10 (15)	C9—C8—H8	111.7
C2—C3—C4	105.96 (14)	C10—C9—C2	104.37 (15)
C12—C3—H3	111.6	C10—C9—C8	110.90 (15)
C2—C3—H3	111.6	C2—C9—C8	110.18 (14)
C4—C3—H3	111.6	C10—C9—H9	110.4
C5—C4—C7	104.15 (16)	C2—C9—H9	110.4
C5—C4—C3	110.29 (15)	C8—C9—H9	110.4
C7—C4—C3	109.89 (14)	O2—C10—O5	120.48 (18)
C5—C4—H4	110.8	O2—C10—C9	129.2 (2)
C7—C4—H4	110.8	O5—C10—C9	110.31 (17)
C3—C4—H4	110.8	C12—C11—C8	114.96 (16)
O3—C5—O6	119.82 (19)	C12—C11—H11	122.5
O3—C5—C4	129.8 (2)	C8—C11—H11	122.5
O6—C5—C4	110.36 (17)	C11—C12—C3	114.75 (17)
O4—C6—O6	120.26 (19)	C11—C12—H12	122.6
O4—C6—C7	129.5 (2)	C3—C12—H12	122.6
O6—C6—C7	110.22 (17)	C10—O5—C1	110.67 (15)
C6—C7—C4	104.49 (15)	C5—O6—C6	110.52 (16)
O1—C1—C2—C9	−175.3 (2)	C4—C7—C8—C9	−62.20 (17)
O5—C1—C2—C9	3.2 (2)	C1—C2—C9—C10	−1.16 (19)
O1—C1—C2—C3	−57.4 (3)	C3—C2—C9—C10	−119.57 (16)
O5—C1—C2—C3	121.13 (17)	C1—C2—C9—C8	117.95 (15)
C1—C2—C3—C12	−59.7 (2)	C3—C2—C9—C8	−0.46 (19)
C9—C2—C3—C12	54.68 (18)	C11—C8—C9—C10	61.6 (2)
C1—C2—C3—C4	−175.28 (15)	C7—C8—C9—C10	176.98 (15)
C9—C2—C3—C4	−60.87 (18)	C11—C8—C9—C2	−53.47 (18)
C12—C3—C4—C5	59.5 (2)	C7—C8—C9—C2	61.93 (17)
C2—C3—C4—C5	174.86 (15)	C2—C9—C10—O2	176.5 (2)
C12—C3—C4—C7	−54.75 (19)	C8—C9—C10—O2	57.9 (3)
C2—C3—C4—C7	60.60 (18)	C2—C9—C10—O5	−1.2 (2)
C7—C4—C5—O3	172.72 (19)	C8—C9—C10—O5	−119.86 (17)
C3—C4—C5—O3	54.9 (3)	C7—C8—C11—C12	−56.8 (2)
C7—C4—C5—O6	−4.85 (19)	C9—C8—C11—C12	56.5 (2)
C3—C4—C5—O6	−122.71 (16)	C8—C11—C12—C3	0.4 (2)
O4—C6—C7—C4	−177.8 (2)	C2—C3—C12—C11	−57.5 (2)
O6—C6—C7—C4	0.55 (19)	C4—C3—C12—C11	56.6 (2)
O4—C6—C7—C8	−59.1 (3)	O2—C10—O5—C1	−174.58 (19)
O6—C6—C7—C8	119.27 (16)	C9—C10—O5—C1	3.4 (2)
C5—C4—C7—C6	2.49 (18)	O1—C1—O5—C10	174.51 (19)
C3—C4—C7—C6	120.62 (15)	C2—C1—O5—C10	−4.2 (2)
C5—C4—C7—C8	−117.01 (16)	O3—C5—O6—C6	−172.38 (18)
C3—C4—C7—C8	1.1 (2)	C4—C5—O6—C6	5.5 (2)
C6—C7—C8—C11	−62.4 (2)	O4—C6—O6—C5	174.79 (18)
C4—C7—C8—C11	52.87 (19)	C7—C6—O6—C5	−3.7 (2)
C6—C7—C8—C9	−177.52 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.98	2.50	3.313 (3)	140
C8—H8···O3ii	0.98	2.58	3.175 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.98	2.50	3.313 (3)	140
C8—H8⋯O3ii	0.98	2.58	3.175 (2)	119

Symmetry codes: (i) ; (ii) .