Low-temperature redetermination of trans-cyclo-hexane-1,2-dicarboxylic acid.

The mol-ecule of the title compound, C(8)H(12)O(4), lies on a twofold rotation axis that passes through the mid-points of two opposite C-C bonds of the ring. Carboxyl groups of adjacent mol-ecules are linked by pairs of hydrogen bonds around a centre of inversion; this inter-action gives rise to a chain that runs along [101].

Related literature

Studies on the metal derivatives of trans-1,2-cyclo­hexa­ne­dicarboxylic acid refer to the room-temperature structure of Benedetti et al. (1969 ▶). The absence of a preferred orientation (either axial or equatorial) of the carboxyl groups in cyclo­hexa­nedicarboxylic acids is discussed in the case of 1,3-cyclo­hexanedicarboxylic acid by van Koningsveld (1984 ▶). For the crystal structure of 1,4-cyclo­hexa­nedicarboxylic acid, see: Luger et al. (1972 ▶).

Experimental

Crystal data

C8H12O4

M = 172.18

Monoclinic,

a = 5.585 (1) Å

b = 13.840 (3) Å

c = 10.035 (2) Å

β = 96.114 (3)°

V = 771.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.38 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

2320 measured reflections

883 independent reflections

715 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.07

883 reflections

59 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012592/cv2404sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012592/cv2404Isup2.hkl

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

C8H12O4	F000 = 368
Mr = 172.18	Dx = 1.483 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 739 reflections
a = 5.585 (1) Å	θ = 3.6–28.2º
b = 13.840 (3) Å	µ = 0.12 mm−1
c = 10.035 (2) Å	T = 100 (2) K
β = 96.114 (3)º	Strip, colourless
V = 771.3 (3) Å3	0.38 × 0.06 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	715 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.9º
ω scans	h = −7→7
Absorption correction: None	k = −17→17
2320 measured reflections	l = −13→8
883 independent reflections

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.2009P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
883 reflections	Δρmax = 0.31 e Å−3
59 parameters	Δρmin = −0.28 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.0840 (2)	0.1596 (1)	0.0902 (1)	0.0173 (3)
O2	0.4725 (2)	0.1968 (1)	0.0869 (1)	0.0166 (3)
C1	0.3157 (3)	0.1471 (1)	0.1279 (2)	0.0122 (3)
C2	0.3668 (2)	0.0626 (1)	0.2220 (2)	0.0122 (4)
C3	0.2893 (3)	−0.0314 (1)	0.1475 (2)	0.0139 (4)
C4	0.3647 (3)	−0.1208 (1)	0.2303 (2)	0.0159 (4)
H1o	0.068 (4)	0.206 (1)	0.035 (2)	0.036 (6)*
H2	0.2676	0.0704	0.2986	0.015*
H3a	0.1121	−0.0315	0.1261	0.017*
H3b	0.3626	−0.0339	0.0620	0.017*
H4a	0.2799	−0.1218	0.3120	0.019*
H4b	0.3184	−0.1796	0.1776	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0124 (6)	0.0179 (6)	0.0205 (7)	0.0008 (4)	−0.0027 (5)	0.0074 (5)
O2	0.0149 (6)	0.0153 (6)	0.0186 (6)	−0.0017 (4)	−0.0028 (4)	0.0048 (4)
C1	0.0140 (7)	0.0112 (7)	0.0107 (8)	0.0012 (5)	−0.0025 (6)	−0.0034 (6)
C2	0.0115 (7)	0.0118 (7)	0.0126 (8)	0.0003 (5)	−0.0025 (6)	−0.0004 (6)
C3	0.0138 (7)	0.0141 (7)	0.0134 (8)	−0.0013 (5)	−0.0012 (6)	−0.0014 (6)
C4	0.0170 (8)	0.0109 (7)	0.0190 (9)	−0.0011 (5)	−0.0012 (6)	0.0003 (6)

O1—C1	1.321 (2)	O1—H1o	0.85 (1)
O2—C1	1.220 (2)	C2—H2	1.0000
C1—C2	1.511 (2)	C3—H3a	0.9900
C2—C2i	1.533 (3)	C3—H3b	0.9900
C2—C3	1.5397 (19)	C4—H4a	0.9900
C3—C4	1.523 (2)	C4—H4b	0.9900
C4—C4i	1.521 (3)
O2—C1—O1	123.1 (1)	C3—C2—H2	108.3
O2—C1—C2	123.6 (1)	C4—C3—H3a	109.2
O1—C1—C2	113.3 (1)	C2—C3—H3a	109.2
C1—C2—C2i	109.9 (1)	C4—C3—H3b	109.2
C1—C2—C3	109.0 (1)	C2—C3—H3b	109.2
C2i—C2—C3	112.9 (1)	H3a—C3—H3b	107.9
C4—C3—C2	112.0 (1)	C4i—C4—H4a	109.5
C4i—C4—C3	110.5 (1)	C3—C4—H4a	109.5
C1—O1—H1o	109 (1)	C4i—C4—H4b	109.5
C1—C2—H2	108.3	C3—C4—H4b	109.5
C2i—C2—H2	108.3	H4a—C4—H4b	108.1
O2—C1—C2—C2i	11.2 (2)	C1—C2—C3—C4	172.7 (1)
O1—C1—C2—C2i	−171.2 (1)	C2i—C2—C3—C4	50.2 (2)
O2—C1—C2—C3	−113.0 (2)	C2—C3—C4—C4i	−56.6 (2)
O1—C1—C2—C3	64.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ii	0.85 (1)	1.81 (1)	2.662 (2)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.85 (1)	1.81 (1)	2.662 (2)	178 (2)

Symmetry code: (i) .