The achiral
meso title compound, C
9H
14O
3, is an intermediate for a series of structurally unique compounds. Intermolecular O—H
O hydrogen bonds produce centrosymmetric
R22(8) rings which dimerize the molecules through the carboxyl group, while C—H
O interactions through the carboxyl α-H atom and the ketone O atom interconnect the dimers
via centrosymmetric
R44(24) rings, producing infinite one-dimensional dimeric ribbons.
Supporting information
CCDC reference: 643642
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.109
- Data-to-parameter ratio = 17.0
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.767 0.987
Tmin(prime) and Tmax expected: 0.977 0.987
RR(prime) = 0.785
Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 500 Deg.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT and SADABS (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and
SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
2,6-Dimethyl-4-oxocyclohexanecarboxylic acid
top
Crystal data top
C9H14O3 | Z = 2 |
Mr = 170.20 | F(000) = 184 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
Hall symbol: -P 1 | Melting point = 436–437 K |
a = 5.2850 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.9516 (6) Å | Cell parameters from 1768 reflections |
c = 12.1889 (9) Å | θ = 3.4–27.1° |
α = 92.039 (5)° | µ = 0.09 mm−1 |
β = 93.401 (5)° | T = 100 K |
γ = 95.967 (5)° | Irregular, colorless |
V = 444.21 (6) Å3 | 0.24 × 0.24 × 0.14 mm |
Data collection top
Bruker Kappa-APEXII CCD area-detector diffractometer | 1907 independent reflections |
Radiation source: X-ray tube | 1383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 27.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −6→6 |
Tmin = 0.767, Tmax = 0.987 | k = −8→8 |
6305 measured reflections | l = −15→15 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.045P)2 + 0.1427P] where P = (Fo2 + 2Fc2)/3 |
1907 reflections | (Δ/σ)max < 0.001 |
112 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2554 (2) | 0.58765 (18) | 0.94013 (9) | 0.0233 (3) | |
O2 | −0.1491 (2) | 0.62235 (18) | 0.88727 (9) | 0.0231 (3) | |
H2 | −0.1774 | 0.5587 | 0.9414 | 0.035* | |
O3 | 0.7499 (2) | 0.9280 (2) | 0.58383 (10) | 0.0311 (4) | |
C1 | 0.1741 (3) | 0.7612 (2) | 0.77803 (13) | 0.0162 (4) | |
H1 | 0.0226 | 0.8133 | 0.7457 | 0.019* | |
C2 | 0.2685 (3) | 0.6210 (2) | 0.69197 (13) | 0.0187 (4) | |
H2A | 0.4163 | 0.5650 | 0.7250 | 0.022* | |
C3 | 0.3518 (3) | 0.7333 (3) | 0.59155 (14) | 0.0216 (4) | |
H3A | 0.4251 | 0.6473 | 0.5408 | 0.026* | |
H3B | 0.2035 | 0.7783 | 0.5539 | 0.026* | |
C4 | 0.5428 (3) | 0.9029 (3) | 0.62358 (14) | 0.0222 (4) | |
C5 | 0.4600 (3) | 1.0380 (3) | 0.70982 (14) | 0.0243 (4) | |
H5A | 0.3197 | 1.1028 | 0.6791 | 0.029* | |
H5B | 0.6000 | 1.1361 | 0.7314 | 0.029* | |
C6 | 0.3753 (3) | 0.9312 (2) | 0.81209 (14) | 0.0190 (4) | |
H6 | 0.5240 | 0.8794 | 0.8472 | 0.023* | |
C7 | 0.0986 (3) | 0.6496 (2) | 0.87674 (13) | 0.0162 (4) | |
C8 | 0.0633 (3) | 0.4572 (3) | 0.65612 (15) | 0.0247 (4) | |
H8A | −0.0866 | 0.5104 | 0.6277 | 0.037* | |
H8B | 0.0225 | 0.3810 | 0.7181 | 0.037* | |
H8C | 0.1245 | 0.3769 | 0.5999 | 0.037* | |
C9 | 0.2751 (3) | 1.0712 (3) | 0.89447 (15) | 0.0256 (4) | |
H9A | 0.1248 | 1.1192 | 0.8625 | 0.038* | |
H9B | 0.4033 | 1.1776 | 0.9127 | 0.038* | |
H9C | 0.2343 | 1.0048 | 0.9599 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0197 (6) | 0.0284 (7) | 0.0219 (7) | 0.0007 (5) | −0.0001 (5) | 0.0113 (5) |
O2 | 0.0177 (6) | 0.0298 (8) | 0.0225 (7) | 0.0011 (5) | 0.0039 (5) | 0.0121 (6) |
O3 | 0.0211 (7) | 0.0444 (9) | 0.0300 (8) | 0.0050 (6) | 0.0071 (5) | 0.0180 (6) |
C1 | 0.0153 (8) | 0.0170 (9) | 0.0165 (9) | 0.0013 (7) | 0.0000 (6) | 0.0049 (7) |
C2 | 0.0205 (9) | 0.0183 (9) | 0.0175 (9) | 0.0025 (7) | 0.0005 (7) | 0.0020 (7) |
C3 | 0.0246 (9) | 0.0240 (10) | 0.0168 (9) | 0.0036 (7) | 0.0028 (7) | 0.0034 (7) |
C4 | 0.0214 (9) | 0.0273 (10) | 0.0193 (9) | 0.0049 (7) | 0.0003 (7) | 0.0150 (8) |
C5 | 0.0255 (10) | 0.0200 (10) | 0.0268 (10) | −0.0032 (7) | 0.0024 (8) | 0.0069 (8) |
C6 | 0.0188 (8) | 0.0181 (9) | 0.0198 (9) | 0.0007 (7) | −0.0004 (7) | 0.0030 (7) |
C7 | 0.0165 (8) | 0.0151 (9) | 0.0170 (9) | 0.0019 (6) | 0.0000 (6) | −0.0004 (7) |
C8 | 0.0314 (10) | 0.0194 (10) | 0.0223 (10) | 0.0005 (8) | −0.0023 (8) | 0.0002 (8) |
C9 | 0.0313 (10) | 0.0197 (10) | 0.0252 (10) | 0.0012 (8) | 0.0005 (8) | −0.0002 (8) |
Geometric parameters (Å, º) top
O1—C7 | 1.2212 (19) | C3—H3B | 0.9700 |
O2—C7 | 1.3174 (19) | C4—C5 | 1.500 (3) |
O2—H2 | 0.8200 | C5—C6 | 1.539 (2) |
O3—C4 | 1.222 (2) | C5—H5A | 0.9700 |
C1—C7 | 1.506 (2) | C5—H5B | 0.9700 |
C1—C6 | 1.533 (2) | C6—C9 | 1.529 (2) |
C1—C2 | 1.546 (2) | C6—H6 | 0.9800 |
C1—H1 | 0.9800 | C8—H8A | 0.9600 |
C2—C8 | 1.521 (2) | C8—H8B | 0.9600 |
C2—C3 | 1.537 (2) | C8—H8C | 0.9600 |
C2—H2A | 0.9800 | C9—H9A | 0.9600 |
C3—C4 | 1.494 (2) | C9—H9B | 0.9600 |
C3—H3A | 0.9700 | C9—H9C | 0.9600 |
| | | |
C7—O2—H2 | 109.5 | C4—C5—H5B | 109.2 |
C7—C1—C6 | 110.59 (13) | C6—C5—H5B | 109.2 |
C7—C1—C2 | 108.86 (13) | H5A—C5—H5B | 107.9 |
C6—C1—C2 | 112.27 (13) | C9—C6—C1 | 111.39 (14) |
C7—C1—H1 | 108.3 | C9—C6—C5 | 110.38 (14) |
C6—C1—H1 | 108.3 | C1—C6—C5 | 110.02 (14) |
C2—C1—H1 | 108.3 | C9—C6—H6 | 108.3 |
C8—C2—C3 | 109.92 (14) | C1—C6—H6 | 108.3 |
C8—C2—C1 | 111.55 (14) | C5—C6—H6 | 108.3 |
C3—C2—C1 | 109.58 (14) | O1—C7—O2 | 123.39 (15) |
C8—C2—H2A | 108.6 | O1—C7—C1 | 122.24 (15) |
C3—C2—H2A | 108.6 | O2—C7—C1 | 114.36 (14) |
C1—C2—H2A | 108.6 | C2—C8—H8A | 109.5 |
C4—C3—C2 | 111.85 (14) | C2—C8—H8B | 109.5 |
C4—C3—H3A | 109.2 | H8A—C8—H8B | 109.5 |
C2—C3—H3A | 109.2 | C2—C8—H8C | 109.5 |
C4—C3—H3B | 109.2 | H8A—C8—H8C | 109.5 |
C2—C3—H3B | 109.2 | H8B—C8—H8C | 109.5 |
H3A—C3—H3B | 107.9 | C6—C9—H9A | 109.5 |
O3—C4—C3 | 122.86 (18) | C6—C9—H9B | 109.5 |
O3—C4—C5 | 122.88 (17) | H9A—C9—H9B | 109.5 |
C3—C4—C5 | 114.25 (14) | C6—C9—H9C | 109.5 |
C4—C5—C6 | 112.00 (14) | H9A—C9—H9C | 109.5 |
C4—C5—H5A | 109.2 | H9B—C9—H9C | 109.5 |
C6—C5—H5A | 109.2 | | |
| | | |
C7—C1—C2—C8 | 59.25 (17) | C7—C1—C6—C9 | −59.96 (18) |
C6—C1—C2—C8 | −177.98 (14) | C2—C1—C6—C9 | 178.25 (14) |
C7—C1—C2—C3 | −178.81 (13) | C7—C1—C6—C5 | 177.31 (14) |
C6—C1—C2—C3 | −56.03 (17) | C2—C1—C6—C5 | 55.51 (18) |
C8—C2—C3—C4 | 176.73 (15) | C4—C5—C6—C9 | −176.08 (14) |
C1—C2—C3—C4 | 53.81 (19) | C4—C5—C6—C1 | −52.76 (19) |
C2—C3—C4—O3 | 125.42 (17) | C6—C1—C7—O1 | −52.9 (2) |
C2—C3—C4—C5 | −53.8 (2) | C2—C1—C7—O1 | 70.9 (2) |
O3—C4—C5—C6 | −126.11 (17) | C6—C1—C7—O2 | 128.23 (16) |
C3—C4—C5—C6 | 53.09 (19) | C2—C1—C7—O2 | −107.98 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.84 | 2.6573 (16) | 177 |
C1—H1···O3ii | 0.98 | 2.57 | 3.476 (2) | 153 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x−1, y, z. |