Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones
Abstract
:1. Introduction
2. Materials and Methods
Synthesis and Crystallization
3. Results
4. Discussion
Crystal Packing
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | I | II | III | IV |
---|---|---|---|---|
Crystal system | Monoclinic | Monoclinic | Monoclinic | Monoclinic |
Unit cell parameters [Å,°] | a = 9.6000(7) b = 5.3426(4) c = 22.353(2) β = 97.307(2) | a = 7.4561(4) b = 7.2591(4) c = 17.7744(10) β = 94.505(2) | a = 13.0205(10) b = 8.0494(6) c = 14.1040(11) β = 114.852(2) | a = 4.9301(18) b = 23.652(9) c = 10.014(4) β = 97.692(12) |
Volume [Å3] | 1137.17(14) | 959.06(9) | 1341.32(18) | 1157.2(8) |
Z/Calculated density [mg/m3] | 4/1.205 | 4/1.324 | 4/1.220 | 4/1.327 |
Z′ | 1 | 1 | 1 | 1 |
Absorption coefficient [mm−1] | 0.086 | 0.099 | 0.084 | 0.095 |
Space group, F (000) | P21/n, 440 | P21/n, 400 | P21/c, 528 | P21/c, 488 |
Index ranges | −11 ≤ h ≤ 11 −6 ≤ k ≤ 6 −25 ≤ l ≤ 26 | −8 ≤ h ≤ 9 −9 ≤ k ≤ 9 −23 ≤ l ≤ 21 | −15 ≤ h ≤ 15 −8 ≤ k ≤ 9 −11 ≤ l ≤ 16 | −6 ≤ h ≤ 6 −30 ≤ k ≤ 30 −13 ≤ l ≤ 13 |
Reflections collected | 6066 | 16,684 | 5906 | 31,441 |
Independent reflections | 2071 [R(int) = 0.0722] | 2446 [R(int) = 0.0940] | 2442 [R(int) = 0.1320] | 2663 [R(int) = 0.1187] |
Observed reflections (I ≥ 2σ(I)) | 1100 | 935 | 1383 | 1290 |
Completeness to θ = 25.10 | 99.6% | 99.8% | 99.6% | 99.7% |
Data/restraints/parameters | 2071/0/139 | 2194/247/441 | 2442/ 72/195 | 2663/0/155 |
Final R indices (I ≥ 2σ(I)) | R1 = 0.0482 wR2 = 0.1026 | R1 = 0.0532 wR2 = 0.1047 | R1 = 0.0631 wR2 = 0.1370 | R1 = 0.0516 wR2 = 0.0907 |
R indices (all data) | R1 = 0.1005 wR2 = 0.1304 | R1 = 0.1416 wR2 = 0.1670 | R1 = 0.1204 wR2 = 0.1712 | R1 = 0.1469 wR2 = 0.1203 |
Goodness-of-fit on F2 | 0.940 | 0.995 | 1.025 | 1.005 |
Largest diff. peak/hole [e·Å−3] | 0.197/−0.172 | 0.114/−0.131 | 0.198/−0.268 | 0.174/−0.139 |
CCDC deposit number | 2075964 | 2075965 | 2075966 | 2075970 |
Compound | D-H···A | D-H | H···A | D···A | D-H···A | Symmetry Code |
---|---|---|---|---|---|---|
I | C1–H1A···O1 C3–H3···O1 C6–H6···O1 C11–H11B···Cg1 C9–H9···Cg1 C12–H12C···C3,4 | 0.960 0.930 0.930 0.960 0.930 0.960 | 2.61 2.60 2.62 2.84 3.05 2.84 | 3.529(3) 3.503(2) 3.545(3) 3.724(2) 3.733(2) 3.751(2) | 160.3 162.4 173.8 154.0 131.9 143.3 | x, −1+y, z 1−x, 1−y, 1−z 1−x, 1−y, 1−z x, 1+y, z 1/2−x, −1/2+y, 1/2−z 1/2−x, −1/2+y, 1/2−z |
II | C7–H7···O2 C9–H9···O3 C4-H4···O1 C10–H10···O1 | 0.930 0.930 0.930 0.930 | 2.57 2.57 2.72 2.72 | 3.327(9) 3.301(9) 3.559(7) 3.539(6) | 138.9 135.8 150.0 147.9 | −x, −y, 1−z −x+1/2, y+1/2, −z+3/2 1−x, 2−y, 1−z 1−x, 2−y, 1−z |
III | C6–H6A···O1 C9–H9···O1 C15–H15A··· O2 C15–H15A···O3 C14–H14A···O1 C4B–H4C···O3 | 0.970 0.930 0.960 0.960 0.960 0.970 | 2.59 2.65 2.62 2.80 2.86 2.66 | 3.539(10) 3.467(3) 3.519(3) 3.446(3) 3.806(3) 3.585(10) | 164.5 146.3 155.5 126.0 170.0 159.0 | −x, −y+1, −z+1 1−x, y+1/2, −z+1/2 −x, 1−y, 1−z −x, 1−y, 1−z 1−x, 1−y, 1−z x, 1/2−y, −1/2+z |
IV | C6–H6A···O1 C6–H6B···O1 C7–H7B···O3 C12–H12···O1 C4–H4A···O2 C9–H9···O3 C5–H5···Cg1 C4–H4B···C2,3 | 0.970 0.970 0.960 0.930 0.970 0.930 0.980 0.970 | 2.64 2.88 2.68 2.66 2.72 2.73 2.98 2.84 | 3.581(3) 3.829(3) 3.467(3) 3.343(3) 3.327(3) 3.630(3) 3.824(3) 3.788(3) | 162.7 166.0 139.0 131.0 121.0 162.0 145.0 165.0 | −1+x, y, z −x, 1−y, 1−z −1+x, y,1+z 1−x,1−y, 1−z −1+x, 1/2−y, 1/2+z −1+x, 1/2−y, 1/2+z −1+x, y, z −1+x, y, z |
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Obregón-Mendoza, M.A.; Arias-Olguín, I.I.; Meza-Morales, W.; Alvarez-Ricardo, Y.; Chávez, M.I.; Toscano, R.A.; Cassani, J.; Enríquez, R.G. Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones. Crystals 2021, 11, 404. https://doi.org/10.3390/cryst11040404
Obregón-Mendoza MA, Arias-Olguín II, Meza-Morales W, Alvarez-Ricardo Y, Chávez MI, Toscano RA, Cassani J, Enríquez RG. Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones. Crystals. 2021; 11(4):404. https://doi.org/10.3390/cryst11040404
Chicago/Turabian StyleObregón-Mendoza, Marco A., Imilla I. Arias-Olguín, William Meza-Morales, Yair Alvarez-Ricardo, María Isabel Chávez, Rubén A. Toscano, Julia Cassani, and Raúl G. Enríquez. 2021. "Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones" Crystals 11, no. 4: 404. https://doi.org/10.3390/cryst11040404
APA StyleObregón-Mendoza, M. A., Arias-Olguín, I. I., Meza-Morales, W., Alvarez-Ricardo, Y., Chávez, M. I., Toscano, R. A., Cassani, J., & Enríquez, R. G. (2021). Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones. Crystals, 11(4), 404. https://doi.org/10.3390/cryst11040404