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The crystal structure of octane-1,8-di­carboxyl­ic acid (sebacic acid), C10H18O4, has been redetermined at 180 K. The molecular units are centrosymmetric and linked via the ubiquitous syn-syn carboxyl­ic acid dimer to form infinite chains running along the [\overline 101] vector.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801000794/bt6002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801000794/bt6002Isup2.hkl
Contains datablock I

CCDC reference: 159745

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.051
  • wR factor = 0.139
  • Data-to-parameter ratio = 18.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry




Comment top

Crystal data for sebacic acid have been reported on four previous occasions, by Caspari (1928), Morrison & Robertson (1949) (SEBAAC01), Housty & Hospital (1966) (SEBAAC) and Haget et al. (1980) (SEBAAC02). All four studies essentially report the same structure in space group P21/c with unit-cell dimensions ca a = 15.1, b = 5.0, c = 10.1 Å, β = 133.1°. [Morrison & Robertson (1949) describe the structure in the non-standard setting P21/a.] The most precise cell determination (SEBAAC02) to date is derived from powder X-ray diffraction data, and atomic coordinates were not determined. We have re-examined sebacic acid at 180 K and report the structure to significantly greater precision in P21/c with β ca 92°. The previously reported structures in P21/c with β ca 133.1° may be transformed to our structure by the matrix (101, 010, 001) followed by an origin shift of (1/2, 1/2, 1/2) to bring an entire molecule into the unit cell.

Experimental top

Sebacic acid was obtained from Aldrich and recrystallized from ethanol.

Refinement top

All H atoms (apart from H1) were placed geometrically and allowed to ride during subsequent refinement with an isotropic displacement parameter fixed at 1.2 times that for the C atom to which they are attached. H1 was refined without restraint.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick 1997); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular unit of the title compound showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Projection onto (010) showing chains of sebacic acid running along the [\-101] vector.
octane-1,8-dicarboxylic acid top
Crystal data top
C10H18O4Dx = 1.239 Mg m3
Mr = 202.24Melting point = 406–408 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 10.9197 (7) ÅCell parameters from 2040 reflections
b = 4.9876 (6) Åθ = 1.0–27.5°
c = 9.964 (1) ŵ = 0.10 mm1
β = 92.273 (6)°T = 180 K
V = 542.27 (9) Å3Plate, colourless
Z = 20.23 × 0.18 × 0.05 mm
F(000) = 220
Data collection top
Nonius KappaCCD
diffractometer
1241 independent reflections
Radiation source: fine-focus sealed tube796 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Thin–slice ω and ϕ scansθmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1114
Tmin = 0.912, Tmax = 0.995k = 56
3745 measured reflectionsl = 129
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0705P)2]
where P = (Fo2 + 2Fc2)/3
1241 reflections(Δ/σ)max = 0.006
68 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C10H18O4V = 542.27 (9) Å3
Mr = 202.24Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.9197 (7) ŵ = 0.10 mm1
b = 4.9876 (6) ÅT = 180 K
c = 9.964 (1) Å0.23 × 0.18 × 0.05 mm
β = 92.273 (6)°
Data collection top
Nonius KappaCCD
diffractometer
1241 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
796 reflections with I > 2σ(I)
Tmin = 0.912, Tmax = 0.995Rint = 0.054
3745 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.22 e Å3
1241 reflectionsΔρmin = 0.18 e Å3
68 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.12859 (9)0.4028 (2)0.92528 (12)0.0427 (4)
O20.01144 (9)0.7593 (3)0.88045 (12)0.0445 (4)
H10.042 (2)0.685 (6)0.959 (3)0.117 (9)*
C10.10498 (13)0.6043 (4)0.85865 (16)0.0332 (4)
C20.18124 (13)0.6970 (4)0.74613 (16)0.0372 (5)
H2A0.21440.87670.76910.045*
H2B0.12730.71660.66450.045*
C30.28703 (13)0.5157 (3)0.71336 (16)0.0365 (5)
H3A0.25510.33430.69190.044*
H3B0.34340.50070.79330.044*
C40.35752 (14)0.6183 (4)0.59603 (18)0.0427 (5)
H4A0.30050.63140.51660.051*
H4B0.38700.80170.61740.051*
C50.46563 (15)0.4497 (4)0.55935 (18)0.0436 (5)
H5A0.43640.26550.53950.052*
H5B0.52350.43950.63820.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0410 (7)0.0463 (9)0.0418 (7)0.0036 (6)0.0153 (5)0.0111 (6)
O20.0424 (7)0.0477 (9)0.0449 (8)0.0095 (6)0.0183 (5)0.0105 (6)
C10.0319 (9)0.0361 (11)0.0318 (9)0.0012 (7)0.0053 (6)0.0005 (8)
C20.0375 (8)0.0399 (11)0.0350 (9)0.0000 (7)0.0112 (7)0.0064 (8)
C30.0340 (9)0.0384 (10)0.0377 (10)0.0009 (7)0.0100 (7)0.0048 (8)
C40.0415 (10)0.0450 (12)0.0427 (10)0.0048 (8)0.0157 (7)0.0104 (9)
C50.0419 (9)0.0451 (11)0.0451 (10)0.0049 (8)0.0175 (8)0.0104 (9)
Geometric parameters (Å, º) top
O1—C11.2263 (19)C3—H3A0.9900
O2—C11.3061 (19)C3—H3B0.9900
O2—H11.06 (3)C4—C51.506 (2)
C1—C21.496 (2)C4—H4A0.9900
C2—C31.513 (2)C4—H4B0.9900
C2—H2A0.9900C5—C5i1.511 (3)
C2—H2B0.9900C5—H5A0.9900
C3—C41.514 (2)C5—H5B0.9900
C1—O2—H1111.8 (14)C4—C3—H3B109.1
O1—C1—O2122.96 (14)H3A—C3—H3B107.9
O1—C1—C2123.21 (14)C5—C4—C3115.21 (15)
O2—C1—C2113.83 (15)C5—C4—H4A108.5
C1—C2—C3115.45 (14)C3—C4—H4A108.5
C1—C2—H2A108.4C5—C4—H4B108.5
C3—C2—H2A108.4C3—C4—H4B108.5
C1—C2—H2B108.4H4A—C4—H4B107.5
C3—C2—H2B108.4C4—C5—C5i115.04 (19)
H2A—C2—H2B107.5C4—C5—H5A108.5
C2—C3—C4112.38 (14)C5i—C5—H5A108.5
C2—C3—H3A109.1C4—C5—H5B108.5
C4—C3—H3A109.1C5i—C5—H5B108.5
C2—C3—H3B109.1H5A—C5—H5B107.5
O1—C1—C2—C33.5 (2)C2—C3—C4—C5179.01 (16)
O2—C1—C2—C3177.21 (14)C3—C4—C5—C5i179.0 (2)
C1—C2—C3—C4178.31 (15)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1ii1.06 (3)1.58 (3)2.6406 (15)175 (2)
Symmetry code: (ii) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC10H18O4
Mr202.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)180
a, b, c (Å)10.9197 (7), 4.9876 (6), 9.964 (1)
β (°) 92.273 (6)
V3)542.27 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.23 × 0.18 × 0.05
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.912, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
3745, 1241, 796
Rint0.054
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.139, 1.05
No. of reflections1241
No. of parameters68
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.18

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick 1997), SHELXL97 (Sheldrick 1997), XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1i1.06 (3)1.58 (3)2.6406 (15)175 (2)
Symmetry code: (i) x, y+1, z+2.
 

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