Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025317/wn2144sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025317/wn2144Isup2.hkl |
CCDC reference: 657794
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.123
- Data-to-parameter ratio = 19.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.63 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 5.47 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.39 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Hu et al. (2003); Li & Strobel (2001); Luu et al. (2004).
A solution of 4,4-di(isopropyloxycarbonyl)-2,6-heptanedione (300 mg, 1 mmol) and sodium methoxide (54 mg, 1 mmol) in methanol (10 ml) was heated at 323 K for 4 h. The reaction mixture was acidified with dilute aqueous HCl, then concentrated and partitioned between water and dichloromethane. The pure product was obtained through silica gel chromatography (eluant petroleum ether/ethyl acetate, 5:1), and diffraction quality crystals were obtained by slow evaporation of a diethyl ether/hexane (1:3) solu- tion at room temperature.
All H atoms were placed in calculated positions, with C—H distances in the range 0.93–0.98 Å and included in the final cycles of refinement in the riding-model approximation, with Uiso(H) = 1.2Ueq(C).
The cyclohex-2-enone ring system is highly reactive and derivatives can be used to synthesize some complex compounds, such as vitamin E, amino acids, terpenes etc. (Hu et al., 2003). In addition, cyclohex-2-enone derivatives have shown a wide range of biological activities such as antimicrobial (Li et al., 2001) and the protection of cerebral neurocytes (Luu et al., 2004). We are interested in their pharmaceutical activity. In this paper, we present an X-ray crystallographic analysis of the title compound. The plane which is composed of C1,C2,C6 and the plane which is composed of C2,C3, C4,C5,C6 form a dihedral angle of 44.9 (2)°.
For related literature, see: Hu et al. (2003); Li & Strobel (2001); Luu et al. (2004).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level. |
C15H22O5 | F(000) = 608.00 |
Mr = 282.34 | Dx = 1.196 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 11337 reflections |
a = 12.302 (3) Å | θ = 3.1–27.5° |
b = 8.909 (3) Å | µ = 0.09 mm−1 |
c = 14.409 (6) Å | T = 298 K |
β = 96.859 (14)° | Block, colorless |
V = 1568.0 (9) Å3 | 0.32 × 0.28 × 0.26 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.025 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5° |
ω scans | h = −14→15 |
15048 measured reflections | k = −11→11 |
3564 independent reflections | l = −18→18 |
2299 reflections with F2 > 2σ(F2) |
Refinement on F2 | w = 1/[0.0011Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.042 | (Δ/σ)max < 0.001 |
wR(F2) = 0.123 | Δρmax = 0.27 e Å−3 |
S = 1.01 | Δρmin = −0.19 e Å−3 |
3564 reflections | Extinction correction: Larson (1970), equation 22 |
182 parameters | Extinction coefficient: 160 (35) |
H-atom parameters constrained |
C15H22O5 | V = 1568.0 (9) Å3 |
Mr = 282.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.302 (3) Å | µ = 0.09 mm−1 |
b = 8.909 (3) Å | T = 298 K |
c = 14.409 (6) Å | 0.32 × 0.28 × 0.26 mm |
β = 96.859 (14)° |
Rigaku R-AXIS RAPID diffractometer | 2299 reflections with F2 > 2σ(F2) |
15048 measured reflections | Rint = 0.025 |
3564 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 182 parameters |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.27 e Å−3 |
3564 reflections | Δρmin = −0.19 e Å−3 |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.81333 (10) | 0.99331 (12) | 0.68321 (9) | 0.0752 (3) | |
O2 | 0.84308 (6) | 0.45934 (11) | 0.57521 (8) | 0.0587 (3) | |
O3 | 0.67627 (8) | 0.37808 (11) | 0.59798 (9) | 0.0669 (3) | |
O4 | 0.67440 (8) | 0.60283 (11) | 0.41615 (6) | 0.0556 (2) | |
O5 | 0.76178 (9) | 0.81440 (12) | 0.46250 (8) | 0.0694 (3) | |
C1 | 0.70689 (10) | 0.64352 (13) | 0.57863 (9) | 0.0425 (3) | |
C2 | 0.78210 (11) | 0.73547 (14) | 0.64992 (10) | 0.0497 (3) | |
C3 | 0.74691 (12) | 0.89631 (16) | 0.65636 (10) | 0.0542 (4) | |
C4 | 0.63088 (12) | 0.92857 (17) | 0.63461 (11) | 0.0596 (4) | |
C5 | 0.55626 (11) | 0.82376 (16) | 0.60862 (10) | 0.0528 (4) | |
C6 | 0.58809 (10) | 0.66294 (13) | 0.59738 (10) | 0.0489 (3) | |
C7 | 0.73776 (10) | 0.47728 (14) | 0.58521 (9) | 0.0456 (3) | |
C8 | 0.88911 (12) | 0.30794 (17) | 0.58361 (12) | 0.0648 (4) | |
C9 | 1.00390 (16) | 0.3266 (2) | 0.62810 (16) | 0.1043 (7) | |
C10 | 0.88125 (19) | 0.2399 (2) | 0.48880 (17) | 0.1116 (8) | |
C11 | 0.71947 (10) | 0.69858 (14) | 0.48006 (9) | 0.0443 (3) | |
C12 | 0.67282 (12) | 0.64383 (17) | 0.31749 (10) | 0.0546 (4) | |
C13 | 0.69216 (19) | 0.5012 (2) | 0.26693 (13) | 0.1015 (7) | |
C14 | 0.56709 (14) | 0.7170 (2) | 0.28566 (12) | 0.0875 (6) | |
C15 | 0.43618 (12) | 0.8564 (2) | 0.58951 (13) | 0.0768 (5) | |
H4 | 0.6076 | 1.0273 | 0.6391 | 0.071* | |
H8 | 0.8479 | 0.2470 | 0.6240 | 0.078* | |
H12 | 0.7326 | 0.7142 | 0.3109 | 0.066* | |
H21 | 0.8556 | 0.7336 | 0.6318 | 0.060* | |
H22 | 0.7824 | 0.6894 | 0.7109 | 0.060* | |
H61 | 0.5408 | 0.6203 | 0.5454 | 0.059* | |
H62 | 0.5778 | 0.6093 | 0.6543 | 0.059* | |
H91 | 1.0468 | 0.3727 | 0.5845 | 0.125* | |
H92 | 1.0342 | 0.2301 | 0.6460 | 0.125* | |
H93 | 1.0047 | 0.3890 | 0.6825 | 0.125* | |
H101 | 0.8065 | 0.2419 | 0.4607 | 0.134* | |
H102 | 0.9257 | 0.2960 | 0.4508 | 0.134* | |
H103 | 0.9065 | 0.1379 | 0.4937 | 0.134* | |
H131 | 0.6329 | 0.4329 | 0.2722 | 0.122* | |
H132 | 0.6964 | 0.5227 | 0.2022 | 0.122* | |
H133 | 0.7596 | 0.4565 | 0.2940 | 0.122* | |
H141 | 0.5603 | 0.8071 | 0.3211 | 0.105* | |
H142 | 0.5082 | 0.6499 | 0.2946 | 0.105* | |
H143 | 0.5641 | 0.7417 | 0.2206 | 0.105* | |
H151 | 0.4104 | 0.8301 | 0.5261 | 0.092* | |
H152 | 0.3974 | 0.7987 | 0.6312 | 0.092* | |
H153 | 0.4237 | 0.9614 | 0.5990 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0967 (8) | 0.0489 (6) | 0.0753 (8) | −0.0152 (5) | −0.0089 (5) | −0.0077 (5) |
O2 | 0.0551 (5) | 0.0444 (5) | 0.0785 (7) | 0.0083 (4) | 0.0159 (4) | 0.0110 (4) |
O3 | 0.0670 (6) | 0.0405 (5) | 0.0966 (9) | −0.0047 (4) | 0.0245 (5) | −0.0005 (5) |
O4 | 0.0761 (6) | 0.0495 (5) | 0.0398 (5) | −0.0127 (4) | 0.0018 (4) | 0.0014 (4) |
O5 | 0.0998 (8) | 0.0551 (6) | 0.0553 (6) | −0.0250 (5) | 0.0176 (5) | −0.0011 (5) |
C1 | 0.0492 (6) | 0.0361 (6) | 0.0420 (7) | 0.0012 (5) | 0.0042 (5) | −0.0006 (5) |
C2 | 0.0589 (7) | 0.0423 (7) | 0.0458 (8) | −0.0011 (5) | −0.0023 (5) | 0.0001 (5) |
C3 | 0.0772 (9) | 0.0417 (7) | 0.0423 (7) | −0.0039 (6) | 0.0015 (6) | −0.0014 (5) |
C4 | 0.0816 (9) | 0.0409 (7) | 0.0554 (9) | 0.0117 (7) | 0.0045 (7) | −0.0032 (6) |
C5 | 0.0647 (8) | 0.0499 (8) | 0.0441 (7) | 0.0105 (6) | 0.0076 (5) | −0.0004 (6) |
C6 | 0.0531 (7) | 0.0451 (7) | 0.0494 (7) | 0.0003 (5) | 0.0095 (5) | −0.0004 (5) |
C7 | 0.0538 (7) | 0.0408 (7) | 0.0427 (7) | 0.0006 (5) | 0.0073 (5) | 0.0008 (5) |
C8 | 0.0699 (9) | 0.0486 (8) | 0.0783 (11) | 0.0186 (7) | 0.0192 (7) | 0.0141 (7) |
C9 | 0.0969 (13) | 0.1152 (17) | 0.0959 (16) | 0.0267 (12) | −0.0085 (11) | 0.0057 (13) |
C10 | 0.1302 (17) | 0.0905 (15) | 0.1088 (18) | 0.0378 (13) | −0.0072 (13) | −0.0317 (13) |
C11 | 0.0492 (6) | 0.0382 (6) | 0.0455 (7) | 0.0011 (5) | 0.0063 (5) | −0.0007 (5) |
C12 | 0.0659 (8) | 0.0570 (8) | 0.0404 (7) | −0.0069 (6) | 0.0043 (5) | 0.0037 (6) |
C13 | 0.160 (2) | 0.0858 (14) | 0.0605 (12) | 0.0185 (13) | 0.0222 (12) | −0.0092 (10) |
C14 | 0.0870 (11) | 0.1104 (16) | 0.0641 (11) | 0.0197 (11) | 0.0047 (8) | 0.0177 (10) |
C15 | 0.0692 (10) | 0.0719 (11) | 0.0881 (13) | 0.0225 (8) | 0.0040 (8) | −0.0023 (9) |
O1—C3 | 1.2201 (18) | C2—H22 | 0.970 |
O2—C7 | 1.3303 (15) | C4—H4 | 0.930 |
O2—C8 | 1.4623 (17) | C6—H61 | 0.970 |
O3—C7 | 1.1918 (16) | C6—H62 | 0.970 |
O4—C11 | 1.3271 (15) | C8—H8 | 0.980 |
O4—C12 | 1.4657 (16) | C9—H91 | 0.960 |
O5—C11 | 1.1963 (17) | C9—H92 | 0.960 |
C1—C2 | 1.5347 (17) | C9—H93 | 0.960 |
C1—C6 | 1.5275 (18) | C10—H101 | 0.960 |
C1—C7 | 1.5291 (18) | C10—H102 | 0.960 |
C1—C11 | 1.5279 (18) | C10—H103 | 0.960 |
C2—C3 | 1.5030 (19) | C12—H12 | 0.980 |
C3—C4 | 1.453 (2) | C13—H131 | 0.960 |
C4—C5 | 1.331 (2) | C13—H132 | 0.960 |
C5—C6 | 1.4992 (19) | C13—H133 | 0.960 |
C5—C15 | 1.498 (2) | C14—H141 | 0.960 |
C8—C9 | 1.489 (2) | C14—H142 | 0.960 |
C8—C10 | 1.487 (2) | C14—H143 | 0.960 |
C12—C13 | 1.498 (2) | C15—H151 | 0.960 |
C12—C14 | 1.478 (2) | C15—H152 | 0.960 |
C2—H21 | 0.970 | C15—H153 | 0.960 |
C7—O2—C8 | 118.32 (10) | C5—C6—H62 | 108.5 |
C11—O4—C12 | 117.96 (10) | H61—C6—H62 | 109.5 |
C2—C1—C6 | 109.53 (10) | O2—C8—H8 | 109.7 |
C2—C1—C7 | 110.49 (9) | C9—C8—H8 | 109.7 |
C2—C1—C11 | 109.33 (10) | C10—C8—H8 | 109.7 |
C6—C1—C7 | 109.54 (10) | C8—C9—H91 | 109.5 |
C6—C1—C11 | 109.47 (10) | C8—C9—H92 | 109.5 |
C7—C1—C11 | 108.46 (10) | C8—C9—H93 | 109.5 |
C1—C2—C3 | 113.28 (10) | H91—C9—H92 | 109.5 |
O1—C3—C2 | 120.53 (12) | H91—C9—H93 | 109.5 |
O1—C3—C4 | 122.12 (13) | H92—C9—H93 | 109.5 |
C2—C3—C4 | 117.26 (12) | C8—C10—H101 | 109.5 |
C3—C4—C5 | 123.26 (13) | C8—C10—H102 | 109.5 |
C4—C5—C6 | 121.36 (12) | C8—C10—H103 | 109.5 |
C4—C5—C15 | 123.17 (13) | H101—C10—H102 | 109.5 |
C6—C5—C15 | 115.47 (12) | H101—C10—H103 | 109.5 |
C1—C6—C5 | 113.27 (10) | H102—C10—H103 | 109.5 |
O2—C7—O3 | 124.89 (12) | O4—C12—H12 | 109.3 |
O2—C7—C1 | 110.34 (10) | C13—C12—H12 | 109.3 |
O3—C7—C1 | 124.77 (11) | C14—C12—H12 | 109.3 |
O2—C8—C9 | 105.70 (13) | C12—C13—H131 | 109.5 |
O2—C8—C10 | 108.54 (14) | C12—C13—H132 | 109.5 |
C9—C8—C10 | 113.29 (16) | C12—C13—H133 | 109.5 |
O4—C11—O5 | 124.33 (12) | H131—C13—H132 | 109.5 |
O4—C11—C1 | 111.00 (10) | H131—C13—H133 | 109.5 |
O5—C11—C1 | 124.64 (11) | H132—C13—H133 | 109.5 |
O4—C12—C13 | 106.01 (12) | C12—C14—H141 | 109.5 |
O4—C12—C14 | 108.67 (12) | C12—C14—H142 | 109.5 |
C13—C12—C14 | 114.10 (14) | C12—C14—H143 | 109.5 |
C1—C2—H21 | 108.5 | H141—C14—H142 | 109.5 |
C1—C2—H22 | 108.5 | H141—C14—H143 | 109.5 |
C3—C2—H21 | 108.5 | H142—C14—H143 | 109.5 |
C3—C2—H22 | 108.5 | C5—C15—H151 | 109.5 |
H21—C2—H22 | 109.5 | C5—C15—H152 | 109.5 |
C3—C4—H4 | 118.4 | C5—C15—H153 | 109.5 |
C5—C4—H4 | 118.4 | H151—C15—H152 | 109.5 |
C1—C6—H61 | 108.5 | H151—C15—H153 | 109.5 |
C1—C6—H62 | 108.5 | H152—C15—H153 | 109.5 |
C5—C6—H61 | 108.5 | ||
C7—O2—C8—C9 | −145.40 (14) | C6—C1—C7—O3 | 3.75 (18) |
C7—O2—C8—C10 | 92.77 (16) | C7—C1—C6—C5 | 170.15 (10) |
C8—O2—C7—O3 | −2.3 (2) | C6—C1—C11—O4 | −73.28 (13) |
C8—O2—C7—C1 | 177.34 (11) | C6—C1—C11—O5 | 104.93 (14) |
C11—O4—C12—C13 | 142.78 (13) | C11—C1—C6—C5 | −71.04 (13) |
C11—O4—C12—C14 | −94.17 (15) | C7—C1—C11—O4 | 46.20 (13) |
C12—O4—C11—O5 | −2.24 (19) | C7—C1—C11—O5 | −135.59 (13) |
C12—O4—C11—C1 | 175.98 (10) | C11—C1—C7—O2 | 64.69 (12) |
C2—C1—C6—C5 | 48.81 (14) | C11—C1—C7—O3 | −115.68 (14) |
C6—C1—C2—C3 | −51.44 (15) | C1—C2—C3—O1 | −154.97 (13) |
C2—C1—C7—O2 | −55.13 (14) | C1—C2—C3—C4 | 28.45 (18) |
C2—C1—C7—O3 | 124.50 (14) | O1—C3—C4—C5 | −177.37 (15) |
C7—C1—C2—C3 | −172.20 (11) | C2—C3—C4—C5 | −0.8 (2) |
C2—C1—C11—O4 | 166.74 (10) | C3—C4—C5—C6 | −1.7 (2) |
C2—C1—C11—O5 | −15.05 (17) | C3—C4—C5—C15 | 177.76 (15) |
C11—C1—C2—C3 | 68.51 (14) | C4—C5—C6—C1 | −23.65 (19) |
C6—C1—C7—O2 | −175.88 (10) | C15—C5—C6—C1 | 156.86 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.98 | 2.47 | 3.333 (2) | 147 |
C12—H12···O5 | 0.98 | 2.35 | 2.707 (2) | 101 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H22O5 |
Mr | 282.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 12.302 (3), 8.909 (3), 14.409 (6) |
β (°) | 96.859 (14) |
V (Å3) | 1568.0 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.28 × 0.26 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 15048, 3564, 2299 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.123, 1.01 |
No. of reflections | 3564 |
No. of parameters | 182 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.19 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure.
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.98 | 2.47 | 3.333 (2) | 147 |
C12—H12···O5 | 0.98 | 2.35 | 2.707 (2) | 101 |
Symmetry code: (i) x, y−1, z. |
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The cyclohex-2-enone ring system is highly reactive and derivatives can be used to synthesize some complex compounds, such as vitamin E, amino acids, terpenes etc. (Hu et al., 2003). In addition, cyclohex-2-enone derivatives have shown a wide range of biological activities such as antimicrobial (Li et al., 2001) and the protection of cerebral neurocytes (Luu et al., 2004). We are interested in their pharmaceutical activity. In this paper, we present an X-ray crystallographic analysis of the title compound. The plane which is composed of C1,C2,C6 and the plane which is composed of C2,C3, C4,C5,C6 form a dihedral angle of 44.9 (2)°.