cis-Cyclo-hexane-1,4-dicarboxylic acid.

In the title compound, C(8)H(12)O(4), the two carboxyl groups are on the same side of the cyclohexane ring and the ring adopts a chair conformation. Adjacent mol-ecules related by an inversion centre are linked by pairs of O-H⋯O hydrogen bonds, forming a zigzag chain along [1].

Related literature

For related structures, see: Bi et al. (2003 ▶, 2004 ▶); Chen et al. (2006 ▶); Du et al. (2006 ▶); Dunitz & Strickler (1966 ▶); Kurmoo et al. (2003 ▶, 2006 ▶); Luger et al. (1972 ▶).

Experimental

Crystal data

C8H12O4

M = 172.18

Triclinic,

a = 5.2912 (6) Å

b = 6.2611 (6) Å

c = 13.1851 (18) Å

α = 82.505 (10)°

β = 80.309 (11)°

γ = 81.875 (10)°

V = 423.70 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.24 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.989

9807 measured reflections

1925 independent reflections

1222 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.129

S = 1.05

1925 reflections

118 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.19 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/S1600536809016110/is2399sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016110/is2399Isup2.hkl

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

C8H12O4	Z = 2
Mr = 172.18	F(000) = 184
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2912 (6) Å	Cell parameters from 3560 reflections
b = 6.2611 (6) Å	θ = 2.6–26.9°
c = 13.1851 (18) Å	µ = 0.11 mm−1
α = 82.505 (10)°	T = 296 K
β = 80.309 (11)°	Plate, colorless
γ = 81.875 (10)°	0.24 × 0.20 × 0.10 mm
V = 423.70 (9) Å3

Bruker SMART CCD area-detector diffractometer	1925 independent reflections
Radiation source: fine-focus sealed tube	1222 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.979, Tmax = 0.989	k = −7→8
9807 measured reflections	l = −17→17

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.038P)2 + 0.2496P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1925 reflections	Δρmax = 0.27 e Å−3
118 parameters	Δρmin = −0.19 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 (12)

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	0.4359 (3)	0.5154 (3)	0.88398 (12)	0.0583 (5)
O2	0.2703 (4)	0.2964 (3)	1.01503 (13)	0.0620 (5)
O3	0.7370 (4)	−0.1284 (3)	0.57741 (15)	0.0709 (6)
O4	0.8260 (3)	0.2120 (3)	0.55122 (14)	0.0632 (5)
C1	0.2929 (4)	0.3798 (3)	0.91784 (16)	0.0386 (5)
C2	0.1278 (4)	0.2898 (4)	0.85544 (16)	0.0420 (5)
H2	−0.0488	0.3021	0.8932	0.050*
C3	0.2176 (4)	0.0476 (3)	0.84796 (17)	0.0457 (6)
H3A	0.2410	−0.0240	0.9161	0.055*
H3B	0.0853	−0.0174	0.8242	0.055*
C4	0.1185 (4)	0.4153 (4)	0.74843 (17)	0.0493 (6)
H4A	−0.0264	0.3782	0.7208	0.059*
H4B	0.0878	0.5694	0.7557	0.059*
C5	0.4695 (4)	0.0121 (3)	0.77409 (16)	0.0411 (5)
H5A	0.5175	−0.1420	0.7694	0.049*
H5B	0.6056	0.0664	0.8006	0.049*
C6	0.3638 (4)	0.3713 (4)	0.67093 (17)	0.0457 (6)
H6A	0.3350	0.4396	0.6028	0.055*
H6B	0.5029	0.4346	0.6907	0.055*
C7	0.4420 (4)	0.1286 (3)	0.66664 (16)	0.0411 (5)
H7	0.3028	0.0710	0.6423	0.049*
C8	0.6862 (4)	0.0769 (4)	0.59270 (16)	0.0432 (5)
H1	0.369 (7)	0.355 (6)	1.048 (3)	0.106 (12)*
H8	0.898 (8)	−0.163 (6)	0.526 (3)	0.128 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0785 (12)	0.0610 (11)	0.0431 (9)	−0.0335 (10)	−0.0145 (8)	−0.0002 (8)
O2	0.0795 (13)	0.0717 (12)	0.0413 (10)	−0.0360 (10)	−0.0111 (9)	0.0020 (8)
O3	0.0759 (13)	0.0525 (11)	0.0741 (13)	−0.0054 (9)	0.0251 (10)	−0.0191 (9)
O4	0.0571 (11)	0.0595 (11)	0.0685 (12)	−0.0124 (9)	0.0167 (9)	−0.0190 (9)
C1	0.0371 (11)	0.0377 (11)	0.0396 (12)	−0.0004 (9)	−0.0016 (9)	−0.0091 (9)
C2	0.0299 (10)	0.0512 (13)	0.0452 (12)	−0.0048 (9)	0.0017 (9)	−0.0163 (10)
C3	0.0454 (12)	0.0447 (13)	0.0476 (13)	−0.0145 (10)	0.0045 (10)	−0.0131 (10)
C4	0.0422 (12)	0.0544 (14)	0.0531 (14)	0.0066 (10)	−0.0150 (10)	−0.0168 (11)
C5	0.0437 (12)	0.0358 (11)	0.0422 (12)	−0.0034 (9)	0.0003 (9)	−0.0084 (9)
C6	0.0490 (13)	0.0490 (13)	0.0378 (12)	0.0017 (10)	−0.0098 (10)	−0.0038 (10)
C7	0.0377 (11)	0.0491 (13)	0.0383 (11)	−0.0058 (9)	−0.0051 (9)	−0.0122 (9)
C8	0.0450 (12)	0.0483 (14)	0.0366 (11)	−0.0024 (10)	−0.0057 (9)	−0.0097 (10)

O1—C1	1.209 (2)	C3—H3B	0.9700
O2—C1	1.312 (3)	C4—C6	1.527 (3)
O2—H1	0.88 (4)	C4—H4A	0.9700
O3—C8	1.310 (3)	C4—H4B	0.9700
O3—H8	1.01 (4)	C5—C7	1.526 (3)
O4—C8	1.217 (3)	C5—H5A	0.9700
C1—C2	1.503 (3)	C5—H5B	0.9700
C2—C4	1.528 (3)	C6—C7	1.523 (3)
C2—C3	1.534 (3)	C6—H6A	0.9700
C2—H2	0.9800	C6—H6B	0.9700
C3—C5	1.520 (3)	C7—C8	1.505 (3)
C3—H3A	0.9700	C7—H7	0.9800
C1—O2—H1	110 (2)	H4A—C4—H4B	107.6
C8—O3—H8	114 (2)	C3—C5—C7	110.71 (18)
O1—C1—O2	121.6 (2)	C3—C5—H5A	109.5
O1—C1—C2	124.7 (2)	C7—C5—H5A	109.5
O2—C1—C2	113.66 (19)	C3—C5—H5B	109.5
C1—C2—C4	113.11 (18)	C7—C5—H5B	109.5
C1—C2—C3	109.99 (18)	H5A—C5—H5B	108.1
C4—C2—C3	111.41 (17)	C7—C6—C4	111.18 (19)
C1—C2—H2	107.3	C7—C6—H6A	109.4
C4—C2—H2	107.3	C4—C6—H6A	109.4
C3—C2—H2	107.3	C7—C6—H6B	109.4
C5—C3—C2	111.67 (17)	C4—C6—H6B	109.4
C5—C3—H3A	109.3	H6A—C6—H6B	108.0
C2—C3—H3A	109.3	C8—C7—C6	113.13 (18)
C5—C3—H3B	109.3	C8—C7—C5	109.85 (18)
C2—C3—H3B	109.3	C6—C7—C5	111.08 (17)
H3A—C3—H3B	107.9	C8—C7—H7	107.5
C6—C4—C2	114.13 (18)	C6—C7—H7	107.5
C6—C4—H4A	108.7	C5—C7—H7	107.5
C2—C4—H4A	108.7	O4—C8—O3	122.7 (2)
C6—C4—H4B	108.7	O4—C8—C7	123.5 (2)
C2—C4—H4B	108.7	O3—C8—C7	113.8 (2)
O1—C1—C2—C4	−10.6 (3)	C2—C4—C6—C7	51.0 (2)
O2—C1—C2—C4	169.74 (18)	C4—C6—C7—C8	−178.86 (18)
O1—C1—C2—C3	114.7 (2)	C4—C6—C7—C5	−54.8 (2)
O2—C1—C2—C3	−65.0 (2)	C3—C5—C7—C8	−175.50 (17)
C1—C2—C3—C5	−74.0 (2)	C3—C5—C7—C6	58.6 (2)
C4—C2—C3—C5	52.3 (2)	C6—C7—C8—O4	9.4 (3)
C1—C2—C4—C6	74.9 (2)	C5—C7—C8—O4	−115.3 (2)
C3—C2—C4—C6	−49.6 (2)	C6—C7—C8—O3	−171.16 (19)
C2—C3—C5—C7	−57.3 (2)	C5—C7—C8—O3	64.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1i	0.88 (4)	1.81 (4)	2.684 (2)	178 (4)
O3—H8···O4ii	1.01 (4)	1.65 (4)	2.658 (2)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1i	0.88 (4)	1.81 (4)	2.684 (2)	178 (4)
O3—H8⋯O4ii	1.01 (4)	1.65 (4)	2.658 (2)	175 (4)

Symmetry codes: (i) ; (ii) .