(1R*,2S*,4S*,5R*)-Cyclo-hexane-1,2:4,5-tetra-carb-oxy-lic dianhydride.

The title compound, C(10)H(8)O(6), a promising raw material to obtain colorless polyimides which are applied to microelectronic and optoelectronic devices, adopts a folded conformation in which the dihedral angle between the two anhydro rings is 55.15 (8)°. The central six-membered ring assumes a conformation inter-mediate between boat and twist-boat. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming a layer parallel to the bc plane.

Related literature

For microelectronic applications of the present compound, see: Ando et al. (2010 ▶). For background to polyimides, see: Hasegawa et al. (2007 ▶, 2008 ▶); Hasegawa & Horie (2001 ▶). For a related structure, see: Uchida et al. (2003 ▶).

Experimental

Crystal data

C10H8O6

M = 224.16

Monoclinic,

a = 12.167 (2) Å

b = 7.1380 (14) Å

c = 10.626 (2) Å

β = 90.12 (3)°

V = 922.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.51 × 0.42 × 0.42 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.945

6648 measured reflections

2285 independent reflections

2015 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.140

S = 1.00

2285 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (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: PLATON (Spek, 2009 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003571/is5043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003571/is5043Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003571/is5043Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812003571/is5043Isup4.cml

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

C10H8O6	F(000) = 464
Mr = 224.16	Dx = 1.613 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3549 reflections
a = 12.167 (2) Å	θ = 2.5–28.3°
b = 7.1380 (14) Å	µ = 0.14 mm−1
c = 10.626 (2) Å	T = 296 K
β = 90.12 (3)°	Block, colorless
V = 922.8 (3) Å3	0.51 × 0.42 × 0.42 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2285 independent reflections
Radiation source: fine-focus sealed tube	2015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.3°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.934, Tmax = 0.945	k = −9→9
6648 measured reflections	l = −7→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0954P)2 + 0.121P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2285 reflections	Δρmax = 0.30 e Å−3
146 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.057 (8)

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	1.05049 (8)	−0.0274 (2)	0.67601 (13)	0.0712 (4)
O2	0.97350 (9)	0.22073 (16)	0.58580 (11)	0.0583 (3)
O3	0.85376 (13)	0.43198 (17)	0.50962 (13)	0.0773 (4)
O4	0.54696 (9)	0.16073 (17)	0.83493 (12)	0.0642 (3)
O5	0.61479 (8)	−0.12795 (16)	0.85526 (9)	0.0504 (3)
O6	0.68964 (10)	−0.40914 (17)	0.82316 (12)	0.0662 (4)
C1	0.85268 (9)	0.02100 (17)	0.69704 (11)	0.0371 (3)
H1	0.8492	0.0003	0.7881	0.045*
C2	0.79051 (10)	0.20009 (16)	0.66127 (11)	0.0382 (3)
H2	0.7781	0.2748	0.7373	0.046*
C3	0.68030 (11)	0.16836 (17)	0.59459 (13)	0.0439 (3)
H3A	0.6350	0.2794	0.6032	0.053*
H3B	0.6930	0.1473	0.5056	0.053*
C4	0.62021 (9)	0.00055 (17)	0.65005 (11)	0.0374 (3)
H4	0.5530	−0.0204	0.6010	0.045*
C5	0.68715 (10)	−0.18238 (16)	0.65113 (11)	0.0363 (3)
H5	0.6573	−0.2689	0.5881	0.044*
C6	0.80993 (10)	−0.15105 (16)	0.62629 (12)	0.0401 (3)
H6A	0.8509	−0.2608	0.6528	0.048*
H6B	0.8216	−0.1342	0.5367	0.048*
C7	0.96943 (10)	0.0603 (2)	0.65718 (13)	0.0479 (3)
C8	0.86994 (13)	0.3023 (2)	0.57707 (14)	0.0508 (4)
C9	0.58864 (9)	0.0285 (2)	0.78582 (13)	0.0431 (3)
C10	0.66715 (10)	−0.2597 (2)	0.78074 (13)	0.0434 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0325 (5)	0.0985 (10)	0.0825 (9)	0.0007 (5)	−0.0011 (5)	0.0044 (7)
O2	0.0524 (6)	0.0621 (7)	0.0605 (7)	−0.0161 (5)	0.0189 (5)	−0.0008 (5)
O3	0.1034 (10)	0.0551 (7)	0.0736 (8)	−0.0151 (7)	0.0130 (7)	0.0214 (6)
O4	0.0493 (6)	0.0756 (8)	0.0679 (7)	0.0162 (5)	0.0054 (5)	−0.0189 (6)
O5	0.0465 (5)	0.0679 (7)	0.0369 (5)	0.0015 (4)	0.0045 (4)	0.0062 (4)
O6	0.0716 (7)	0.0576 (7)	0.0694 (7)	0.0034 (5)	0.0005 (6)	0.0278 (6)
C1	0.0332 (5)	0.0456 (6)	0.0326 (5)	−0.0024 (4)	0.0015 (4)	0.0029 (5)
C2	0.0437 (6)	0.0349 (6)	0.0359 (6)	−0.0044 (4)	0.0042 (5)	−0.0022 (4)
C3	0.0494 (7)	0.0388 (6)	0.0436 (7)	0.0024 (5)	−0.0066 (5)	0.0077 (5)
C4	0.0318 (5)	0.0427 (6)	0.0377 (6)	0.0014 (4)	−0.0066 (4)	0.0019 (5)
C5	0.0359 (6)	0.0361 (6)	0.0368 (6)	−0.0030 (4)	0.0003 (4)	0.0013 (4)
C6	0.0365 (6)	0.0379 (6)	0.0461 (7)	0.0009 (4)	0.0073 (5)	−0.0005 (5)
C7	0.0383 (6)	0.0595 (8)	0.0460 (7)	−0.0094 (6)	0.0031 (5)	−0.0051 (6)
C8	0.0627 (9)	0.0427 (7)	0.0471 (7)	−0.0126 (6)	0.0090 (6)	0.0006 (6)
C9	0.0282 (5)	0.0548 (7)	0.0464 (7)	0.0024 (5)	−0.0005 (5)	−0.0042 (5)
C10	0.0368 (6)	0.0487 (7)	0.0447 (7)	−0.0040 (5)	−0.0011 (5)	0.0091 (5)

O1—C7	1.1850 (19)	C2—C3	1.5322 (18)
O2—C7	1.3745 (19)	C2—H2	0.9800
O2—C8	1.391 (2)	C3—C4	1.5226 (17)
O3—C8	1.1869 (19)	C3—H3A	0.9700
O4—C9	1.1923 (17)	C3—H3B	0.9700
O5—C9	1.3754 (18)	C4—C9	1.5070 (18)
O5—C10	1.3853 (18)	C4—C5	1.5390 (16)
O6—C10	1.1898 (18)	C4—H4	0.9800
C1—C7	1.5095 (17)	C5—C10	1.5039 (17)
C1—C6	1.5304 (17)	C5—C6	1.5341 (17)
C1—C2	1.5328 (17)	C5—H5	0.9800
C1—H1	0.9800	C6—H6A	0.9700
C2—C8	1.5068 (18)	C6—H6B	0.9700
C7—O2—C8	110.60 (10)	C5—C4—H4	108.4
C9—O5—C10	110.53 (10)	C10—C5—C6	111.75 (10)
C7—C1—C6	109.29 (10)	C10—C5—C4	103.39 (10)
C7—C1—C2	103.86 (10)	C6—C5—C4	112.99 (9)
C6—C1—C2	112.36 (10)	C10—C5—H5	109.5
C7—C1—H1	110.4	C6—C5—H5	109.5
C6—C1—H1	110.4	C4—C5—H5	109.5
C2—C1—H1	110.4	C1—C6—C5	111.25 (10)
C8—C2—C3	111.02 (11)	C1—C6—H6A	109.4
C8—C2—C1	103.55 (10)	C5—C6—H6A	109.4
C3—C2—C1	114.98 (10)	C1—C6—H6B	109.4
C8—C2—H2	109.0	C5—C6—H6B	109.4
C3—C2—H2	109.0	H6A—C6—H6B	108.0
C1—C2—H2	109.0	O1—C7—O2	120.18 (13)
C4—C3—C2	110.96 (9)	O1—C7—C1	129.62 (14)
C4—C3—H3A	109.4	O2—C7—C1	110.16 (12)
C2—C3—H3A	109.4	O3—C8—O2	121.05 (14)
C4—C3—H3B	109.4	O3—C8—C2	129.08 (16)
C2—C3—H3B	109.4	O2—C8—C2	109.86 (12)
H3A—C3—H3B	108.0	O4—C9—O5	120.41 (13)
C9—C4—C3	112.95 (11)	O4—C9—C4	129.29 (13)
C9—C4—C5	103.95 (10)	O5—C9—C4	110.30 (10)
C3—C4—C5	114.57 (10)	O6—C10—O5	119.85 (13)
C9—C4—H4	108.4	O6—C10—C5	129.67 (14)
C3—C4—H4	108.4	O5—C10—C5	110.48 (11)
C7—C1—C2—C8	13.48 (13)	C6—C1—C7—O2	109.53 (12)
C6—C1—C2—C8	−104.52 (11)	C2—C1—C7—O2	−10.57 (13)
C7—C1—C2—C3	134.77 (11)	C7—O2—C8—O3	−172.68 (15)
C6—C1—C2—C3	16.77 (14)	C7—O2—C8—C2	6.61 (15)
C8—C2—C3—C4	155.23 (11)	C3—C2—C8—O3	42.5 (2)
C1—C2—C3—C4	38.11 (15)	C1—C2—C8—O3	166.44 (16)
C2—C3—C4—C9	63.98 (13)	C3—C2—C8—O2	−136.70 (12)
C2—C3—C4—C5	−54.81 (14)	C1—C2—C8—O2	−12.78 (14)
C9—C4—C5—C10	11.25 (11)	C10—O5—C9—O4	−176.99 (12)
C3—C4—C5—C10	134.99 (11)	C10—O5—C9—C4	3.01 (13)
C9—C4—C5—C6	−109.73 (11)	C3—C4—C9—O4	45.97 (18)
C3—C4—C5—C6	14.02 (14)	C5—C4—C9—O4	170.76 (14)
C7—C1—C6—C5	−172.96 (10)	C3—C4—C9—O5	−134.04 (11)
C2—C1—C6—C5	−58.22 (13)	C5—C4—C9—O5	−9.25 (12)
C10—C5—C6—C1	−74.30 (13)	C9—O5—C10—O6	−175.24 (13)
C4—C5—C6—C1	41.81 (13)	C9—O5—C10—C5	4.90 (14)
C8—O2—C7—O1	−179.25 (14)	C6—C5—C10—O6	−68.34 (18)
C8—O2—C7—C1	2.77 (15)	C4—C5—C10—O6	169.85 (14)
C6—C1—C7—O1	−68.20 (19)	C6—C5—C10—O5	111.50 (11)
C2—C1—C7—O1	171.70 (15)	C4—C5—C10—O5	−10.31 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O3i	0.98	2.40	3.3384 (19)	159
C3—H3B···O6ii	0.97	2.58	3.429 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O3i	0.98	2.40	3.3384 (19)	159
C3—H3B⋯O6ii	0.97	2.58	3.429 (2)	146

Symmetry codes: (i) ; (ii) .