Synthesis, X-ray Structure, Conformational Analysis, and DFT Studies of a Giant s-Triazine bis-Schiff Base
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis of 2,2′-(6-(piperidin-1-yl)-1,3,5-triazine-2,4-diyl)bis(hydrazin-2 -yl-1-ylidene))bis(methanylylidene))diphenol; 4
2.2. X-ray Structure Determinations
3. Computational Details
4. Results and Discussion
4.1. Crystal Structure Description
4.2. Analysis of Molecular Packing
4.3. Conformational Analysis
4.4. Optimized Geometry
4.5. NBO Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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CCDC | 2118553 |
empirical formula | C22H24N8O2 |
Fw | 432.49 |
temp (K) | 120(2) |
λ (Å) | 1.54184 |
Crystal system | Orthorhombic |
space group | Pbca |
a (Å) | 8.1139(2) |
b (Å) | 11.2637(2) |
c (Å) | 45.7836(8) |
V (Å3) | 4184.28(15) |
Z | 8 |
ρcalc (Mg/m3) | 1.373 |
μ (Mo Kα) (mm−1) | 0.762 |
No. reflns. | 29,199 |
Unique reflns. | 4404 |
Completeness to θ = 67.684° | 99.9% |
GOOF (F2) | 1.047 |
Rint | 0.0345 |
R1 a (I ≥ 2σ) | 0.0374 |
wR2 b (I ≥ 2σ) | 0.0911 |
Atoms | Distance | Atoms | Distance |
---|---|---|---|
O1-C1 | 1.3578(14) | N4-C9 | 1.3477(15) |
O2-C22 | 1.3624(16) | N5-C15 | 1.3379(15) |
N1-C7 | 1.2882(15) | N5-C8 | 1.3445(15) |
N1-N2 | 1.3697(13) | N6-C9 | 1.3493(15) |
N2-C8 | 1.3691(15) | N6-C10 | 1.4657(15) |
N3-C8 | 1.3291(15) | N6-C14 | 1.4707(15) |
N3-C9 | 1.3622(15) | N7-C15 | 1.3565(15) |
N4-C15 | 1.3394(15) | N7-N8 | 1.3622(14) |
Atoms | Angle | Atoms | Angle |
C7-N1-N2 | 116.50(10) | C10-N6-C14 | 114.56(10) |
C8-N2-N1 | 121.50(10) | C15-N7-N8 | 120.60(10) |
C8-N3-C9 | 113.29(10) | C16-N8-N7 | 117.41(10) |
C15-N4-C9 | 113.93(10) | O1-C1-C2 | 118.15(11) |
C15-N5-C8 | 112.03(10) | O1-C1-C6 | 121.81(11) |
C9-N6-C10 | 122.81(10) | C2-C1-C6 | 120.03(11) |
C9-N6-C14 | 121.91(10) | C3-C2-C1 | 120.06(12) |
D-H...A | d(D-H) | d(H...A) | d(D...A) | <(DHA) |
---|---|---|---|---|
O1-H1...N1 | 0.958(2) | 1.789(2) | 2.648(1) | 147.6(2) |
O2-H2...N8 | 0.92(2) | 1.80(2) | 2.608(1) | 145.0(2) |
N7-H7...O2 i | 0.927(2) | 1.996(2) | 2.918(1) | 173.9(2) |
C7-H7A...N3 ii | 0.95 | 2.61 | 3.494(1) | 155.0 |
C10-H10B...N3 | 0.99 | 2.35 | 2.7846(15) | 106.0 |
C12-H12B...O1 iii | 0.99 | 2.57 | 3.2842(15) | 129.0 |
C14-H14A...N4 | 0.99 | 2.29 | 2.7459(16) | 107.0 |
C20-H20...N5 iv | 0.95 | 2.52 | 3.4165(18) | 158.0 |
Contact | Distance | Contact | Distance |
---|---|---|---|
H12A…C5 | 2.747 | H2A…N4 | 2.522 |
H7A…C9 | 2.499 | H7A…N3 | 2.488 |
H7A…C9 | 2.494 | H20…N5 | 2.394 |
H16…C22 | 2.756 | O2…H7 | 1.914 |
H15…C21 | 2.509 | O1…H3 | 2.533 |
C16…C21 | 3.348 | H1…H12B | 2.155 |
C16…C22 | 3.235 | H21…H16 | 2.294 a |
Param. | 4 | 4A | 4B | 4C | 4D | 4E | 4F | 4G | 4H |
---|---|---|---|---|---|---|---|---|---|
E a | −1441.3046 | −1441.2844 | −1441.2635 | −1441.2841 | −1441.286847 | −1441.290592 | −1441.272653 | −1441.276378 | −1441.272801 |
ZPVE a | 0.4535 | 0.4526 | 0.4517 | 0.4525 | 0.452338 | 0.452615 | 0.451841 | 0.452084 | 0.451863 |
Etot a | −1440.8511 | −1440.8318 | −1440.8118 | −1440.8316 | −1440.8345 | −1440.8380 | −1440.8208 | −1440.8243 | −1440.8209 |
∆E b | 0.0000 | 12.0882 | 24.6525 | 12.2360 | 10.4044 | 8.2278 | 18.9990 | 16.8140 | 18.9203 |
H a | −1440.8229 | −1440.8031 | −1440.7827 | −1440.8029 | −1440.805625 | −1440.80919 | −1440.791531 | −1440.795082 | −1440.791662 |
∆H b | 0.0000 | 12.3787 | 25.2167 | 12.5274 | 10.8118 | 8.5748 | 19.6558 | 17.4276 | 19.5736 |
G a | −1440.9125 | −1440.8946 | −1440.8756 | −1440.8942 | −1440.897779 | −1440.900977 | −1440.884482 | −1440.887956 | −1440.884582 |
∆G b | 0.0000 | 11.2197 | 23.1635 | 11.4368 | 9.2211 | 7.2144 | 17.5650 | 15.3850 | 17.5022 |
S c | 188.6180 | 192.5080 | 195.5080 | 192.2760 | 193.953 | 193.183 | 195.632 | 195.469 | 195.568 |
4I | 4J | 4K | 4L | 4M | 4N | 4O | 4P | ||
E a | −1441.3044 | −1441.2844 | −1441.2638 | −1441.3010 | −1441.2878 | −1441.2597 | −1441.2747 | −1441.2672 | |
ZPVE a | 0.4538 | 0.4526 | 0.4518 | 0.4534 | 0.4526 | 0.4515 | 0.4521 | 0.4516 | |
Etot a | −1440.8506 | −1440.8318 | −1440.8120 | −1440.8475 | −1440.8353 | −1440.8081 | −1440.8227 | −1440.8156 | |
∆E b | 0.2951 | 12.1058 | 24.5161 | 2.2345 | 9.9103 | 26.9448 | 17.8395 | 22.2519 | |
H a | −1440.8228 | −1440.8031 | −1440.7830 | −1440.8192 | −1440.8069 | −1440.7790 | −1440.7935 | −1440.7863 | |
∆H b | 0.0201 | 12.3743 | 25.0285 | 2.2916 | 10.0362 | 27.5096 | 18.4359 | 22.9514 | |
G a | −1440.9125 | −1440.8939 | −1440.8750 | −1440.9093 | −1440.8955 | −1440.8715 | −1440.8856 | −1440.8790 | |
∆G b | 0.0094 | 11.6414 | 23.5444 | 1.9785 | 10.6518 | 25.7024 | 16.8559 | 21.0106 | |
S c | 188.6540 | 191.0780 | 193.5960 | 189.6690 | 186.5540 | 194.6810 | 193.9180 | 195.1290 |
NBOi | NBOj | E(2) | NBOi | NBOj | E(2) |
---|---|---|---|---|---|
σ→σ* | π→π* | ||||
BD(1)O1-H56 | BD*(1)C11-C12 | 5.06 | BD(2)N3-C21 | BD*(2)C18-C20 | 7.87 |
BD(1)O2-H55 | BD*(1)C50-C52 | 5.02 | BD(2)N5-C24 | BD*(2)N 7-C23 | 48.26 |
BD(1)N5-C24 | BD*(1)N 4-C23 | 5.63 | BD(2)N6-C40 | BD*(2)N 5-C24 | 39.11 |
BD(1)N7-C23 | BD*(1)N 9-C40 | 5.99 | BD(2)N7-C23 | BD*(2)N 6-C40 | 45.32 |
BD(1)C20-C21 | BD*(1)N 3-N 4 | 5.22 | BD(2)N10-C41 | BD*(2)C43-C44 | 7.88 |
BD(1)C41-C43 | BD*(1)N 9-N10 | 5.20 | BD(2)C11-C12 | BD*(2)C14-C16 | 25.09 |
BD(2)C11-C12 | BD*(2)C18-C20 | 17.00 | |||
BD(2)C14-C16 | BD*(2)C11-C12 | 17.55 | |||
BD(2)C14-C16 | BD*(2)C18-C20 | 24.64 | |||
BD(2)C18-C20 | BD*(2)N 3-C21 | 24.97 | |||
BD(2)C18-C20 | BD*(2)C11-C12 | 21.73 | |||
n→σ* | n→π* | ||||
LP(1)O 1 | BD*(1)C11-C20 | 7.96 | BD(2)C18-C20 | BD*(2)C14-C16 | 17.03 |
LP(1)O 2 | BD*(1)C43-C52 | 8.02 | BD(2)C43-C44 | BD*(2)N10-C41 | 24.95 |
LP(1)N 3 | BD*(1)O 1-H56 | 24.48 | BD(2)C43-C44 | BD*(2)C46-C48 | 17.02 |
LP(1)N 3 | BD*(1)N 4-H54 | 8.74 | BD(2)C43-C44 | BD*(2)C50-C52 | 21.68 |
LP(1)N 3 | BD*(1)C21-H22 | 9.92 | BD(2)C46-C48 | BD*(2)C43-C44 | 24.65 |
LP(1)N 5 | BD*(1)N 7-C23 | 13.54 | BD(2)C46-C48 | BD*(2)C50-C52 | 17.57 |
LP(1)N 5 | BD*(1)N 6-C24 | 12.09 | BD(2)C50-C52 | BD*(2)C43-C44 | 17.07 |
LP(1)N 6 | BD*(1)N 5-C24 | 11.84 | BD(2)C50-C52 | BD*(2)C46-C48 | 25.10 |
LP(1)N 6 | BD*(1)N 7-C40 | 13.29 | LP(2)O 1 | BD*(2)C11-C12 | 35.52 |
LP(1)N 7 | BD*(1)N 5-C23 | 12.74 | LP(2)O 2 | BD*(2)C50-C52 | 35.53 |
LP(1)N 7 | BD*(1)N 6-C40 | 12.66 | LP(1)N 4 | BD*(2)N 3-C21 | 31.38 |
LP(1)N10 | BD*(1)O 2-H55 | 23.08 | LP(1)N 4 | BD*(2)N 7-C23 | 53.44 |
LP(1)N10 | BD*(1)C41-H42 | 10.00 | LP(1)N 8 | BD*(2)N 5-C24 | 71.52 |
LP(1)N10 | BD*(1)N 9-H53 | 8.82 | LP(1)N 9 | BD*(2)N 6-C40 | 52.75 |
LP(1)N 9 | BD*(2)N10-C41 | 31.48 |
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Almarhoon, Z.M.; Al-Zaben, M.I.; Ben Bacha, A.; Haukka, M.; El-Faham, A.; Soliman, S.M. Synthesis, X-ray Structure, Conformational Analysis, and DFT Studies of a Giant s-Triazine bis-Schiff Base. Crystals 2021, 11, 1418. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst11111418
Almarhoon ZM, Al-Zaben MI, Ben Bacha A, Haukka M, El-Faham A, Soliman SM. Synthesis, X-ray Structure, Conformational Analysis, and DFT Studies of a Giant s-Triazine bis-Schiff Base. Crystals. 2021; 11(11):1418. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst11111418
Chicago/Turabian StyleAlmarhoon, Zainab M., Maha I. Al-Zaben, Abir Ben Bacha, Matti Haukka, Ayman El-Faham, and Saied M. Soliman. 2021. "Synthesis, X-ray Structure, Conformational Analysis, and DFT Studies of a Giant s-Triazine bis-Schiff Base" Crystals 11, no. 11: 1418. https://0-doi-org.brum.beds.ac.uk/10.3390/cryst11111418