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

The title compound, C10H12O8, a prospective raw material for colourless polyimides which are applied to electronic and microelectronic devices, lies about an inversion centre and the cyclo-hexane ring adopts a chair conformation. Two crystallographycally independent carb-oxy-lic acid groups on adjacent C atoms are in equatorial positions, resulting in a mutually trans conformation. In the crystal, O-H⋯O hydrogen bonds around an inversion centre and a threefold rotoinversion axis, respectively, form an inversion dimer with an R 2 (2)(8) motif and a trimer with an R 3 (3)(12) motif.

Related literature

For background to polyimides, see: Ando et al. (2010 ▶); Hasegawa et al. (2007 ▶, 2013 ▶); Hasegawa & Horie (2001 ▶). For related structures, see: Uchida et al. (2003 ▶, 2012 ▶).

Experimental

Crystal data

C10H12O8

M = 260.20

Trigonal,

a = 17.6970 (6) Å

c = 9.5455 (6) Å

V = 2589.0 (2) Å3

Z = 9

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.33 × 0.26 × 0.26 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.891, T max = 0.966

6439 measured reflections

1653 independent reflections

1388 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.06

1653 reflections

90 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.21 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: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033795/is5327sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033795/is5327Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033795/is5327Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033795/is5327Isup4.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H12O8	Dx = 1.502 Mg m−3
Mr = 260.20	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 2340 reflections
a = 17.6970 (6) Å	θ = 2.3–30.0°
c = 9.5455 (6) Å	µ = 0.13 mm−1
V = 2589.0 (2) Å3	T = 298 K
Z = 9	Block, colourless
F(000) = 1224	0.33 × 0.26 × 0.26 mm

Bruker APEXII CCD area-detector diffractometer	1388 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→21
Tmin = 0.891, Tmax = 0.966	k = −20→24
6439 measured reflections	l = −13→11
1653 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0607P)2 + 1.9122P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1653 reflections	Δρmax = 0.38 e Å−3
90 parameters	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.

	x	y	z	Uiso*/Ueq
C1	0.51496 (8)	0.07671 (7)	−0.08154 (11)	0.0279 (3)
H1A	0.4929	0.1116	−0.1242	0.034*
H1B	0.5770	0.1045	−0.1011	0.034*
C2	0.50063 (7)	0.07293 (7)	0.07787 (11)	0.0233 (2)
H2	0.4383	0.0484	0.0969	0.028*
C3	0.53165 (7)	0.01523 (7)	0.14585 (11)	0.0242 (2)
H3	0.5944	0.0414	0.1285	0.029*
C4	0.55013 (8)	0.16503 (7)	0.13456 (12)	0.0283 (3)
C5	0.51702 (8)	0.00882 (8)	0.30236 (12)	0.0267 (3)
O1	0.62253 (6)	0.19739 (7)	0.18327 (13)	0.0471 (3)
H4	0.5352 (17)	0.2558 (18)	0.151 (3)	0.083 (8)*
O2	0.50596 (8)	0.20615 (8)	0.12244 (15)	0.0543 (3)
O3	0.46919 (7)	0.03210 (7)	0.35746 (9)	0.0380 (3)
O4	0.55716 (7)	−0.02417 (7)	0.37025 (10)	0.0400 (3)
H5	0.5485 (19)	−0.0245 (19)	0.467 (3)	0.110 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0389 (6)	0.0247 (5)	0.0218 (5)	0.0171 (5)	0.0021 (4)	0.0033 (4)
C2	0.0259 (5)	0.0227 (5)	0.0214 (5)	0.0123 (4)	0.0009 (4)	0.0002 (4)
C3	0.0274 (5)	0.0268 (5)	0.0198 (5)	0.0147 (4)	0.0014 (4)	0.0015 (4)
C4	0.0309 (6)	0.0246 (5)	0.0267 (5)	0.0119 (5)	0.0041 (4)	0.0008 (4)
C5	0.0310 (6)	0.0282 (5)	0.0214 (5)	0.0153 (5)	−0.0010 (4)	0.0009 (4)
O1	0.0302 (5)	0.0342 (5)	0.0672 (8)	0.0088 (4)	−0.0056 (5)	−0.0095 (5)
O2	0.0559 (7)	0.0333 (5)	0.0820 (9)	0.0285 (5)	−0.0212 (6)	−0.0187 (5)
O3	0.0517 (6)	0.0540 (6)	0.0237 (4)	0.0380 (5)	0.0042 (4)	0.0031 (4)
O4	0.0531 (6)	0.0611 (7)	0.0238 (4)	0.0420 (6)	0.0015 (4)	0.0059 (4)

C1—C3i	1.5370 (16)	C3—H3	0.9800
C1—C2	1.5386 (15)	C4—O1	1.2049 (16)
C1—H1A	0.9700	C4—O2	1.3126 (16)
C1—H1B	0.9700	C5—O3	1.2295 (15)
C2—C4	1.5130 (15)	C5—O4	1.2961 (14)
C2—C3	1.5251 (15)	O2—H4	0.81 (3)
C2—H2	0.9800	O4—H5	0.94 (3)
C3—C5	1.5108 (15)
C3i—C1—C2	111.06 (9)	C5—C3—C1i	109.53 (9)
C3i—C1—H1A	109.4	C2—C3—C1i	110.89 (9)
C2—C1—H1A	109.4	C5—C3—H3	108.3
C3i—C1—H1B	109.4	C2—C3—H3	108.3
C2—C1—H1B	109.4	C1i—C3—H3	108.3
H1A—C1—H1B	108.0	O1—C4—O2	123.84 (12)
C4—C2—C3	111.15 (9)	O1—C4—C2	123.74 (11)
C4—C2—C1	108.23 (9)	O2—C4—C2	112.41 (11)
C3—C2—C1	110.07 (9)	O3—C5—O4	124.14 (11)
C4—C2—H2	109.1	O3—C5—C3	121.25 (10)
C3—C2—H2	109.1	O4—C5—C3	114.60 (10)
C1—C2—H2	109.1	C4—O2—H4	109.5 (18)
C5—C3—C2	111.43 (9)	C5—O4—H5	111.8 (17)
C3i—C1—C2—C4	178.45 (9)	C1—C2—C4—O1	−95.39 (14)
C3i—C1—C2—C3	56.81 (13)	C3—C2—C4—O2	−155.53 (11)
C4—C2—C3—C5	61.11 (12)	C1—C2—C4—O2	83.49 (13)
C1—C2—C3—C5	−179.00 (9)	C2—C3—C5—O3	14.47 (16)
C4—C2—C3—C1i	−176.60 (9)	C1i—C3—C5—O3	−108.61 (13)
C1—C2—C3—C1i	−56.70 (13)	C2—C3—C5—O4	−166.81 (10)
C3—C2—C4—O1	25.59 (16)	C1i—C3—C5—O4	70.12 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4···O1ii	0.81 (3)	1.93 (3)	2.705 (2)	160 (3)
O4—H5···O3iii	0.94 (3)	1.70 (3)	2.632 (1)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H4⋯O1i	0.81 (3)	1.93 (3)	2.705 (2)	160 (3)
O4—H5⋯O3ii	0.94 (3)	1.70 (3)	2.632 (1)	176 (3)

Symmetry codes: (i) ; (ii) .