organic compounds
In the crystal structure of the title compound, C6H10O4, the molecules form chains via centrosymmetrically related pairs of strong O—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014997/rk2001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014997/rk2001Isup2.hkl |
CCDC reference: 647302
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(RS)-2-Methylglutaric acid top
Crystal data top
C6H10O4 | Z = 2 |
Mr = 146.14 | F(000) = 156 |
Triclinic, P1 | Dx = 1.321 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1765 (10) Å | Cell parameters from 2367 reflections |
b = 5.7929 (12) Å | θ = 3.1–27.5° |
c = 13.335 (3) Å | µ = 0.11 mm−1 |
α = 80.92 (3)° | T = 293 K |
β = 83.54 (3)° | Block, colorless |
γ = 68.82 (3)° | 0.33 × 0.21 × 0.2 mm |
V = 367.52 (15) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1605 independent reflections |
Radiation source: fine-focus sealed tube | 1007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −7→7 |
Tmin = 0.702, Tmax = 0.776 | l = −17→17 |
3517 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.0734P] where P = (Fo2 + 2Fc2)/3 |
1605 reflections | (Δ/σ)max < 0.001 |
91 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 1.0121 (4) | 0.2213 (3) | 0.07929 (13) | 0.0766 (6) | |
H1 | 1.1084 | 0.1612 | 0.0283 | 0.092* | |
O2 | 0.7343 (4) | 0.0074 (3) | 0.08234 (13) | 0.0740 (6) | |
O3 | 0.8019 (4) | −0.4989 (3) | 0.42035 (13) | 0.0804 (6) | |
H3 | 0.7525 | −0.6051 | 0.4602 | 0.097* | |
O4 | 0.3877 (4) | −0.2059 (4) | 0.44184 (14) | 0.0835 (6) | |
C1 | 0.8039 (4) | 0.1579 (4) | 0.11706 (15) | 0.0476 (5) | |
C2 | 0.6500 (4) | 0.2884 (4) | 0.20618 (16) | 0.0538 (5) | |
H2A | 0.7817 | 0.3269 | 0.2420 | 0.065* | |
C3 | 0.5202 (4) | 0.1283 (4) | 0.28057 (16) | 0.0567 (6) | |
H3A | 0.4108 | 0.2251 | 0.3336 | 0.068* | |
H3B | 0.3961 | 0.0820 | 0.2452 | 0.068* | |
C4 | 0.7354 (5) | −0.1053 (5) | 0.32858 (18) | 0.0661 (6) | |
H4A | 0.8458 | −0.1989 | 0.2748 | 0.079* | |
H4B | 0.8585 | −0.0568 | 0.3636 | 0.079* | |
C5 | 0.6236 (5) | −0.2726 (5) | 0.40178 (16) | 0.0601 (6) | |
C6 | 0.4319 (5) | 0.5335 (4) | 0.1652 (2) | 0.0722 (7) | |
H6A | 0.5206 | 0.6312 | 0.1192 | 0.087* | |
H6B | 0.3369 | 0.6245 | 0.2207 | 0.087* | |
H6C | 0.3008 | 0.4992 | 0.1298 | 0.087* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0810 (11) | 0.1031 (13) | 0.0695 (11) | −0.0585 (10) | 0.0306 (9) | −0.0405 (10) |
O2 | 0.0881 (12) | 0.0950 (12) | 0.0628 (10) | −0.0592 (11) | 0.0278 (8) | −0.0364 (9) |
O3 | 0.0754 (12) | 0.0827 (12) | 0.0659 (11) | −0.0170 (10) | 0.0086 (8) | 0.0057 (9) |
O4 | 0.0659 (11) | 0.0904 (12) | 0.0753 (12) | −0.0188 (9) | 0.0150 (9) | 0.0100 (9) |
C1 | 0.0505 (11) | 0.0522 (11) | 0.0421 (10) | −0.0221 (9) | 0.0019 (8) | −0.0054 (8) |
C2 | 0.0526 (11) | 0.0622 (12) | 0.0508 (12) | −0.0230 (10) | 0.0054 (9) | −0.0183 (10) |
C3 | 0.0541 (12) | 0.0699 (14) | 0.0448 (11) | −0.0212 (11) | 0.0083 (9) | −0.0130 (10) |
C4 | 0.0568 (13) | 0.0829 (16) | 0.0532 (13) | −0.0223 (12) | 0.0047 (10) | −0.0040 (11) |
C5 | 0.0604 (13) | 0.0764 (15) | 0.0402 (11) | −0.0212 (12) | −0.0015 (9) | −0.0061 (10) |
C6 | 0.0715 (16) | 0.0587 (14) | 0.0838 (18) | −0.0214 (12) | 0.0084 (13) | −0.0141 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.287 (2) | C3—C4 | 1.510 (3) |
O1—H1 | 0.8400 | C3—H3A | 0.9700 |
O2—C1 | 1.223 (3) | C3—H3B | 0.9700 |
O3—C5 | 1.307 (3) | C4—C5 | 1.485 (3) |
O3—H3 | 0.8400 | C4—H4A | 0.9700 |
O4—C5 | 1.226 (3) | C4—H4B | 0.9700 |
C1—C2 | 1.501 (3) | C6—H6A | 0.9600 |
C2—C3 | 1.518 (3) | C6—H6B | 0.9600 |
C2—C6 | 1.525 (3) | C6—H6C | 0.9600 |
C2—H2A | 0.9800 | ||
C1—O1—H1 | 121.2 | H3A—C3—H3B | 107.9 |
C5—O3—H3 | 119.0 | C5—C4—C3 | 115.31 (19) |
O2—C1—O1 | 122.95 (19) | C5—C4—H4A | 108.4 |
O2—C1—C2 | 122.82 (18) | C3—C4—H4A | 108.4 |
O1—C1—C2 | 114.22 (18) | C5—C4—H4B | 108.4 |
C1—C2—C3 | 112.24 (17) | C3—C4—H4B | 108.4 |
C1—C2—C6 | 107.94 (19) | H4A—C4—H4B | 107.5 |
C3—C2—C6 | 111.51 (18) | O4—C5—O3 | 122.8 (2) |
C1—C2—H2A | 108.3 | O4—C5—C4 | 123.6 (2) |
C3—C2—H2A | 108.3 | O3—C5—C4 | 113.54 (19) |
C6—C2—H2A | 108.3 | C2—C6—H6A | 109.5 |
C4—C3—C2 | 112.22 (17) | C2—C6—H6B | 109.5 |
C4—C3—H3A | 109.2 | H6A—C6—H6B | 109.5 |
C2—C3—H3A | 109.2 | C2—C6—H6C | 109.5 |
C4—C3—H3B | 109.2 | H6A—C6—H6C | 109.5 |
C2—C3—H3B | 109.2 | H6B—C6—H6C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.84 | 2.671 (2) | 167 |
O3—H3···O4ii | 0.84 | 1.83 | 2.661 (3) | 171 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y−1, −z+1. |