Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061168/bt2631sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061168/bt2631Isup2.hkl |
CCDC reference: 673096
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B .. O2 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the synthesis of the title compound, see Zaug et al. (1960). For the crystal structures of some compounds bearing two cyclopropane groups bonded to an O-bonded C atom, see Yus et al. (2005); Febles et al. (2004). For the crystal structures of 1-hydroxycarboxylic acids with the methylene unit of glycolic acid being part of smaller-sized hydrocarbon rings, see: Betz & Klüfers (2007a,b,c) where similar as well as different hydrogen-bonding patterns are observed. For the crystal structures of 1-hydroxycarboxylic acids in which the methylene unit of glycolic acid is substituted with sterically more demanding groups, see: Betz & Klüfers (2007d); Betz et al. (2007).
The title compound was prepared according to standard procedures (Zaug et al., 1960) upon aqueous oxidation of 1,1-dicyclopropyl-prop-2-yne-1-ol. Crystals suitable for X-ray analysis were obtained upon the free evaporation of a solution of the compound in diethylether at room temperature.
The H atoms were refined as riding on their parent atoms (Uiso as the 1.2-fold of the parent atom's Ueq). The O-bonded H atoms were refined using SHELXL's electron-density-related AFIX 147 statement.
Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: 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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C8H12O3 | Z = 2 |
Mr = 156.18 | F(000) = 168 |
Triclinic, P1 | Dx = 1.274 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8595 (3) Å | Cell parameters from 3975 reflections |
b = 7.2955 (3) Å | θ = 3.1–26.0° |
c = 10.5515 (5) Å | µ = 0.10 mm−1 |
α = 92.107 (3)° | T = 200 K |
β = 100.758 (3)° | Block, colourless |
γ = 112.263 (3)° | 0.16 × 0.13 × 0.08 mm |
V = 407.22 (3) Å3 |
Nonius KappaCCD diffractometer | 1221 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.026 |
MONTEL, graded multilayered X-ray optics monochromator | θmax = 26.0°, θmin = 3.4° |
CCD; rotation images; thick slices scans | h = −7→7 |
3030 measured reflections | k = −8→8 |
1594 independent reflections | l = −12→12 |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.1023P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1594 reflections | Δρmax = 0.19 e Å−3 |
103 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.096 (12) |
C8H12O3 | γ = 112.263 (3)° |
Mr = 156.18 | V = 407.22 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.8595 (3) Å | Mo Kα radiation |
b = 7.2955 (3) Å | µ = 0.10 mm−1 |
c = 10.5515 (5) Å | T = 200 K |
α = 92.107 (3)° | 0.16 × 0.13 × 0.08 mm |
β = 100.758 (3)° |
Nonius KappaCCD diffractometer | 1221 reflections with I > 2σ(I) |
3030 measured reflections | Rint = 0.026 |
1594 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.19 e Å−3 |
1594 reflections | Δρmin = −0.18 e Å−3 |
103 parameters |
x | y | z | Uiso*/Ueq | ||
O3 | 0.45110 (17) | 0.71307 (15) | 0.64164 (10) | 0.0310 (3) | |
H83 | 0.4429 | 0.6235 | 0.5865 | 0.037* | |
O1 | 0.78873 (19) | 0.61259 (16) | 0.55317 (11) | 0.0356 (3) | |
O2 | 1.11508 (19) | 0.85312 (17) | 0.68539 (12) | 0.0388 (4) | |
H82 | 1.1983 | 0.7962 | 0.6561 | 0.047* | |
C1 | 0.8731 (3) | 0.7539 (2) | 0.63559 (14) | 0.0237 (4) | |
C2 | 0.7095 (2) | 0.8385 (2) | 0.69426 (14) | 0.0231 (4) | |
C3 | 0.7557 (3) | 1.0442 (2) | 0.65394 (15) | 0.0304 (4) | |
H3 | 0.7210 | 1.0464 | 0.5577 | 0.037* | |
C4 | 0.9573 (3) | 1.2317 (2) | 0.7267 (2) | 0.0468 (5) | |
H4A | 1.0446 | 1.3374 | 0.6757 | 0.056* | |
H4B | 1.0650 | 1.2212 | 0.8081 | 0.056* | |
C5 | 0.6863 (3) | 1.1889 (2) | 0.72612 (19) | 0.0451 (5) | |
H5A | 0.6063 | 1.2680 | 0.6746 | 0.054* | |
H5B | 0.6267 | 1.1517 | 0.8070 | 0.054* | |
C6 | 0.7678 (3) | 0.8316 (2) | 0.83998 (15) | 0.0282 (4) | |
H6 | 0.9396 | 0.9278 | 0.8863 | 0.034* | |
C7 | 0.6769 (4) | 0.6371 (3) | 0.89413 (19) | 0.0483 (5) | |
H7A | 0.5677 | 0.5164 | 0.8328 | 0.058* | |
H7B | 0.7929 | 0.6153 | 0.9674 | 0.058* | |
C8 | 0.5697 (3) | 0.7866 (3) | 0.91947 (17) | 0.0397 (5) | |
H8A | 0.6198 | 0.8577 | 1.0083 | 0.048* | |
H8B | 0.3944 | 0.7589 | 0.8736 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0178 (5) | 0.0361 (6) | 0.0352 (7) | 0.0091 (5) | 0.0027 (5) | −0.0136 (5) |
O1 | 0.0252 (6) | 0.0375 (7) | 0.0403 (7) | 0.0106 (5) | 0.0055 (5) | −0.0140 (5) |
O2 | 0.0188 (6) | 0.0469 (7) | 0.0477 (8) | 0.0137 (5) | 0.0024 (5) | −0.0166 (6) |
C1 | 0.0197 (7) | 0.0277 (8) | 0.0242 (8) | 0.0100 (6) | 0.0044 (6) | 0.0013 (6) |
C2 | 0.0167 (7) | 0.0257 (8) | 0.0250 (8) | 0.0077 (6) | 0.0026 (6) | −0.0029 (6) |
C3 | 0.0340 (9) | 0.0326 (9) | 0.0284 (9) | 0.0162 (7) | 0.0088 (7) | 0.0035 (7) |
C4 | 0.0463 (11) | 0.0298 (10) | 0.0559 (12) | 0.0049 (8) | 0.0130 (9) | 0.0055 (8) |
C5 | 0.0573 (12) | 0.0325 (10) | 0.0571 (12) | 0.0238 (9) | 0.0257 (10) | 0.0076 (8) |
C6 | 0.0265 (8) | 0.0331 (8) | 0.0247 (8) | 0.0121 (7) | 0.0043 (6) | 0.0005 (6) |
C7 | 0.0696 (13) | 0.0442 (11) | 0.0415 (11) | 0.0291 (10) | 0.0203 (10) | 0.0149 (8) |
C8 | 0.0403 (10) | 0.0526 (11) | 0.0305 (9) | 0.0199 (8) | 0.0142 (8) | 0.0051 (8) |
O3—C2 | 1.4273 (16) | C4—H4A | 0.9900 |
O3—H83 | 0.8400 | C4—H4B | 0.9900 |
O1—C1 | 1.2046 (17) | C5—H5A | 0.9900 |
O2—C1 | 1.3139 (17) | C5—H5B | 0.9900 |
O2—H82 | 0.8400 | C6—C7 | 1.492 (2) |
C1—C2 | 1.525 (2) | C6—C8 | 1.501 (2) |
C2—C3 | 1.513 (2) | C6—H6 | 1.0000 |
C2—C6 | 1.518 (2) | C7—C8 | 1.489 (2) |
C3—C4 | 1.489 (2) | C7—H7A | 0.9900 |
C3—C5 | 1.497 (2) | C7—H7B | 0.9900 |
C3—H3 | 1.0000 | C8—H8A | 0.9900 |
C4—C5 | 1.497 (3) | C8—H8B | 0.9900 |
C2—O3—H83 | 109.5 | C4—C5—H5A | 117.8 |
C1—O2—H82 | 109.5 | C3—C5—H5A | 117.8 |
O1—C1—O2 | 124.35 (13) | C4—C5—H5B | 117.8 |
O1—C1—C2 | 123.54 (13) | C3—C5—H5B | 117.8 |
O2—C1—C2 | 112.11 (12) | H5A—C5—H5B | 114.9 |
O3—C2—C3 | 108.01 (12) | C7—C6—C8 | 59.66 (11) |
O3—C2—C6 | 109.26 (12) | C7—C6—C2 | 120.19 (14) |
C3—C2—C6 | 114.76 (12) | C8—C6—C2 | 122.65 (13) |
O3—C2—C1 | 108.04 (11) | C7—C6—H6 | 114.5 |
C3—C2—C1 | 109.06 (12) | C8—C6—H6 | 114.5 |
C6—C2—C1 | 107.53 (12) | C2—C6—H6 | 114.5 |
C4—C3—C5 | 60.16 (12) | C8—C7—C6 | 60.49 (11) |
C4—C3—C2 | 124.26 (14) | C8—C7—H7A | 117.7 |
C5—C3—C2 | 121.31 (13) | C6—C7—H7A | 117.7 |
C4—C3—H3 | 113.6 | C8—C7—H7B | 117.7 |
C5—C3—H3 | 113.6 | C6—C7—H7B | 117.7 |
C2—C3—H3 | 113.6 | H7A—C7—H7B | 114.8 |
C3—C4—C5 | 60.20 (11) | C7—C8—C6 | 59.85 (11) |
C3—C4—H4A | 117.8 | C7—C8—H8A | 117.8 |
C5—C4—H4A | 117.8 | C6—C8—H8A | 117.8 |
C3—C4—H4B | 117.8 | C7—C8—H8B | 117.8 |
C5—C4—H4B | 117.8 | C6—C8—H8B | 117.8 |
H4A—C4—H4B | 114.9 | H8A—C8—H8B | 114.9 |
C4—C5—C3 | 59.63 (11) | ||
O1—C1—C2—O3 | 4.3 (2) | C1—C2—C3—C5 | −161.26 (15) |
O2—C1—C2—O3 | −175.78 (12) | C2—C3—C4—C5 | −109.52 (17) |
O1—C1—C2—C3 | −112.91 (16) | C2—C3—C5—C4 | 114.25 (17) |
O2—C1—C2—C3 | 67.05 (16) | O3—C2—C6—C7 | 44.52 (18) |
O1—C1—C2—C6 | 122.07 (16) | C3—C2—C6—C7 | 165.97 (14) |
O2—C1—C2—C6 | −57.96 (16) | C1—C2—C6—C7 | −72.51 (17) |
O3—C2—C3—C4 | 154.67 (14) | O3—C2—C6—C8 | −26.75 (19) |
C6—C2—C3—C4 | 32.5 (2) | C3—C2—C6—C8 | 94.70 (17) |
C1—C2—C3—C4 | −88.14 (18) | C1—C2—C6—C8 | −143.77 (15) |
O3—C2—C3—C5 | 81.55 (17) | C2—C6—C7—C8 | −112.50 (16) |
C6—C2—C3—C5 | −40.6 (2) | C2—C6—C8—C7 | 108.48 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H82···O3i | 0.84 | 1.83 | 2.6387 (16) | 161 |
O3—H83···O1 | 0.84 | 2.15 | 2.6572 (16) | 119 |
O3—H83···O1ii | 0.84 | 2.07 | 2.8067 (15) | 146 |
C8—H8B···O2iii | 0.99 | 2.61 | 3.470 (2) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H12O3 |
Mr | 156.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 200 |
a, b, c (Å) | 5.8595 (3), 7.2955 (3), 10.5515 (5) |
α, β, γ (°) | 92.107 (3), 100.758 (3), 112.263 (3) |
V (Å3) | 407.22 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.16 × 0.13 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3030, 1594, 1221 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.104, 1.04 |
No. of reflections | 1594 |
No. of parameters | 103 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.18 |
Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H82···O3i | 0.84 | 1.83 | 2.6387 (16) | 161 |
O3—H83···O1 | 0.84 | 2.15 | 2.6572 (16) | 119 |
O3—H83···O1ii | 0.84 | 2.07 | 2.8067 (15) | 146 |
C8—H8B···O2iii | 0.99 | 2.61 | 3.470 (2) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |
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2,2-Di(cyclopropyl) glycolic acid (I) was prepared as the parent acid of a potentially chelating ligand bearing two conformationally rigid cyclopropane moieties. The cyclopropane rings are oriented askew to each other (Fig. 1). Bond lengths and angles are normal (Yus et al., 2005, Febles et al., 2004).
Fig. 2 shows hydrophilic chains along the viewing direction embedded in a lipophilic matrix. All the contacts between the atoms of the lipophilic matrix arise at distances larger than the sum of the van-der-Waals radii.
Fig. 3 shows an individual hydrogen-bonded chain. Instead of the frequently found carboxylic-acid dimers, pairs of alcoholic OH and C=O functions are the anchoring points for a dimer. If the C1–C2 σ bond is regarded as being incapable of relaying cooperativity, and if the weakly bifurcated part of the bond from the O3–H donor is neglected, there is—contrary to a pure carboxylic acid dimer—no cooperativity in the dimer. Instead, an extended cooperative motif is formed by the mutual lateral contact of two dimers each: 12-membered, homodromic rings that contain O–H vectors as well as π-cooperativity.
Weak interactions below the sum-of-van-der-Waals-radii limit are sparse. The only contact of this kind is a non-classic C–H···O hydrogen bond that supports the hydrophilic chain along the O2···O3 contact.