Mechanochemical Synthesis of a Cocrystal of Two Supramolecular Hydrogen-Bonded Aggregates of 1,3,6,8-Tetraazatricyclo[4.3.1.13,8]undecane (TATU) with 4-tert-Butylphenol Bearing Different Hydrogen Bonding Interactions
Abstract
:1. Introduction
2. Materials and Methods
2.1. Preparation of TATU-4TBP Cocrystal
2.2. X-Ray Analysis
3. Results and Discussion
3.1. Single Crystal X-Ray Diffraction
3.2. Spectroscopic Properties
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | Parameters |
---|---|
CCDC No. | 1852317 |
Empirical formula | C27H42N4O2 |
Formula weight | 454.64 |
Temperature | 173(2) K |
Crystal system | triclinic |
Space group | P-1 |
Unit cell dimensions | a = 6.2023(5) Å, α = 89.382(6)° |
b = 11.8765(9) Å, β = 86.729(6)° | |
c = 86.729(6) Å, γ = 87.117(6)° | |
Volume | 2607.8(4) Å3 |
Z | 4 |
Calculated density | 1.158 g/cm3 |
Absorption coefficient | 0.074 mm−1 |
F(000) | 992 |
Crystal size mm3 | 0.23 × 0.19 × 0.15 |
θmin/θmax/ o | 1.806/25.480 |
Limiting indices | −7 ≤ h ≤ 7, −14 ≤ k ≤ 13, −42 ≤ l ≤ 42 |
Reflections collected | 37001 |
Independent reflections | 37001 [R(int) = ?] |
Refinement method | Full–matrix least–squares on F2 |
Data/restraints/parameters | 37001/0/612 |
Goodness of fit on F2 | 0.896 |
R1/wR2[I > 2σ(I)] | 0.0606/0.1476 |
R1/wR2(all data) | 0.1016/0.1632 |
Largest diff. peak and hole/e.Å−1 | 0.406/−0.236 |
D–H∙∙∙A | d(D–H) | d(D∙∙∙A) | d(D∙∙∙A) | ∠(DHA) |
---|---|---|---|---|
O(1)–H(1)∙∙∙N(1) | 1.07(5) | 1.57(5) | 2.630(4) | 168(3) |
O(2)–H(2)∙∙∙O(1)#1 | 0.86(4) | 1.84(4) | 2.699(4) | 176(4) |
O(1A)–H(1A)∙∙∙N(1A) | 0.97(5) | 1.71(5) | 2.655(4) | 164(3) |
O(2A)–H(2A)∙∙∙O(1A) | 0.88(4) | 1.86(4) | 2.736(4) | 174(3) |
C(1)–H(1B)∙∙∙N(3)#2 | 0.99 | 2.62 | 3.537(5) | 153.9 |
C(4)–H(4A)∙∙∙O(2)#3 | 0.99 | 2.44 | 3.307(4) | 146.2 |
C(1A)–H(1A1)∙∙∙N(4A)#2 | 0.99 | 2.67 | 3.625(5) | 163.0 |
C(5A)–H(5A2)∙∙∙O(2A)#4 | 0.99 | 2.43 | 3.382(4) | 160.0 |
C(28)–H(28B)∙∙∙Cg1#5 | 0.99 | 2.84 | 3.814(4) | 175.0 |
C(29A)–H(29F) ∙∙Cg2#1 | 0.99 | 2.81 | 3.785(4) | 172.0 |
C(20)–H(20B)∙∙∙Cg3#6 | 0.99 | 2.71 | 3.573(5) | 148.0 |
C(20A)–H(20F)∙∙∙Cg2#7 | 0.99 | 2.83 | 3.579(4) | 134.0 |
C(18A)–H(18F)∙∙∙Cg4#8 | 0.99 | 2.76 | 3.585(4) | 142.0 |
C(2)–H(2C)∙∙∙Cg4#7 | 0.99 | 2.94 | 3.851(5) | 154.0 |
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Rivera, A.; Rojas, J.J.; Ríos-Motta, J.; Bolte, M. Mechanochemical Synthesis of a Cocrystal of Two Supramolecular Hydrogen-Bonded Aggregates of 1,3,6,8-Tetraazatricyclo[4.3.1.13,8]undecane (TATU) with 4-tert-Butylphenol Bearing Different Hydrogen Bonding Interactions. Crystals 2018, 8, 309. https://doi.org/10.3390/cryst8080309
Rivera A, Rojas JJ, Ríos-Motta J, Bolte M. Mechanochemical Synthesis of a Cocrystal of Two Supramolecular Hydrogen-Bonded Aggregates of 1,3,6,8-Tetraazatricyclo[4.3.1.13,8]undecane (TATU) with 4-tert-Butylphenol Bearing Different Hydrogen Bonding Interactions. Crystals. 2018; 8(8):309. https://doi.org/10.3390/cryst8080309
Chicago/Turabian StyleRivera, Augusto, Jicli José Rojas, Jaime Ríos-Motta, and Michael Bolte. 2018. "Mechanochemical Synthesis of a Cocrystal of Two Supramolecular Hydrogen-Bonded Aggregates of 1,3,6,8-Tetraazatricyclo[4.3.1.13,8]undecane (TATU) with 4-tert-Butylphenol Bearing Different Hydrogen Bonding Interactions" Crystals 8, no. 8: 309. https://doi.org/10.3390/cryst8080309