Crystal Structure and Density Functional Theory Study on Structural Properties and Energies of a Isonicotinohydrazide Compound
Abstract
:1. Introduction
2. Results and Discussion
2.1. Molecular Geometry
Identification code | 119 |
Empirical formula | C15H18N4O2 |
Formula weight | 286.33 |
Temperature | 120(2) K |
Wavelength | 0.71073 Å |
Crystal system | Orthorhombic |
Space group | P 21 21 21 |
Unit cell dimensions | a = 7.2272(17) Å |
b = 11.745(3) Å | |
c = 17.177(5) Å | |
Volume | 1458.1(7) Å 3 |
Z | 4 |
Density (calculated) | 1.304 Mg/m3 |
Absorption coefficient | 0.090 mm−1 |
F(000) | 608 |
Crystal size | 0.34 × 0.08 × 0.06 mm3 |
Theta range for data collection | 2.10 to 28.00° |
Index ranges | −9 ≤ h ≤ 9, −15 ≤ k ≤ 15, −22 ≤ l ≤ 22 |
Reflections collected | 15039 |
Independent reflections | 2034 [R(int) = 0.0529] |
Completeness to theta = 28.00° | 100.0% |
Absorption correction | None |
Refinement method | Full-matrix least-squares on F2 |
Data / restraints / parameters | 2034 / 0 / 192 |
Goodness-of-fit on F2 | 0.998 |
Final R indices [for 1694 rfls with I>2sigma(I)] | R1 = 0.0419, wR2 = 0.0848 |
R indices (all data) | R1 = 0.0562, wR2 = 0.0944 |
Largest diff. peak and hole | 0.200 and −0.181 e. Å −3 |
D-H···A | d(D-H) | d(H···A) | d(D···A) | <(DHA) |
---|---|---|---|---|
N(2)-H(2B)···O(1W)#1 | 0.86 | 1.898 | 2.730(3) | 162 |
O(1W)-H(1)···O(1)#2 | 0.85 | 1.962 | 2.717(3) | 147 |
O(1W)-H(2)···N(1)#3 | 0.85 | 1.977 | 2.818(3) | 170 |
Bond lengths | X-ray | B3LYP | PBE1PBE |
---|---|---|---|
C(1)-C(2) | 1.383(3) | 1.403 | 1.399 |
C(1)-C(5) | 1.392(3) | 1.402 | 1.397 |
C(1)-C(6) | 1.504(3) | 1.493 | 1.487 |
C(3)-N(1) | 1.342(3) | 1.352 | 1.347 |
C(4)-N(1) | 1.338(3) | 1.350 | 1.345 |
C(2)-C(3) | 1.382(3) | 1.392 | 1.388 |
C(4)-C(5) | 1.388(3) | 1.395 | 1.392 |
C(6)-O(1) | 1.236(3) | 1.255 | 1.250 |
C(6)-N(2) | 1.342(3) | 1.378 | 1.370 |
C(7)-N(3) | 1.290(3) | 1.301 | 1.297 |
C(7)-C(8) | 1.458(3) | 1.467 | 1.462 |
C(8)-C(9) | 1.398(3) | 1.410 | 1.405 |
C(8)-C(13) | 1.402(3) | 1.411 | 1.406 |
C(9)-C(10) | 1.382(3) | 1.386 | 1.383 |
C(10)-C(11) | 1.410(3) | 1.419 | 1.414 |
C(11)-N(4) | 1.370(3) | 1.384 | 1.376 |
C(11)-C(12) | 1.415(3) | 1.418 | 1.413 |
C(12)-C(13) | 1.385(3) | 1.389 | 1.385 |
C(14)-N(4) | 1.454(3) | 1.464 | 1.452 |
C(15)-N(4) | 1.453(3) | 1.464 | 1.452 |
N(2)-N(3) | 1.398(3) | 1.388 | 1.374 |
Bond angles | X-ray | B3LYP | PBE1PBE |
---|---|---|---|
C(2)-C(1)-C(6) | 118.5(2) | 116.6 | 116.2 |
C(5)-C(1)-C(6) | 122.7(2) | 125.2 | 125.5 |
N(1)-C(3)-C(2) | 123.7(2) | 122.9 | 123.0 |
N(1)-C(4)-C(5) | 123.8(2) | 123.4 | 123.5 |
O(1)-C(6)-N(2) | 125.0(2) | 117.7 | 116.8 |
O(1)-C(6)-C(1) | 119.9(2) | 120.7 | 120.6 |
N(2)-C(6)-C(1) | 115.1(2) | 121.6 | 121.6 |
N(3)-C(7)-C(8) | 122.2(2) | 131.2 | 130.3 |
C(13)-C(8)-C(7) | 122.6(2) | 124.5 | 124.0 |
N(4)-C(11)-C(10) | 121.7(2) | 121.4 | 121.3 |
N(4)-C(11)-C(12) | 121.2(2) | 121.4 | 121.3 |
C(4)-N(1)-C(3) | 116.7(2) | 117.5 | 117.5 |
C(6)-N(2)-N(3) | 119.3(2) | 124.2 | 124.4 |
C(7)-N(3)-N(2) | 113.7(2) | 119.2 | 119.0 |
C(11)-N(4)-C(15) | 120.6(2) | 120.3 | 120.1 |
C(11)-N(4)-C(14) | 121.3(2) | 120.3 | 120.1 |
C(15)-N(4)-C(14) | 118.1(2) | 119.4 | 119.7 |
2.2. IR Spectrum
Freq. | Int. (IR) | B3LYP 6-311G** | Int. (IR) | PBE1PBE 6-311G** | Int. (IR) | Vib. |
---|---|---|---|---|---|---|
3407 | m | 3490 | 30.44 | 3523 | 36.83 | νN–H |
3191 | m | 3157 | 18.03 | 3184 | 14.14 | νC–H (aromatic) |
2928 | m | 2981 | 12.33 | 3002 | 97.84 | νC–H (CH3 symmetric) |
1664 | s | 1633 | 181.51 | 1673 | 216.11 | νC=O |
1593 | s | 1617 | 168.64 | 1661 | 200.13 | νC=N |
1524 | s | 1577 | 16.21 | 1607 | 16.42 | νC=C (aromatic) |
1308 | s | 1340 | 148.77 | 1369 | 112.49 | C–H methyl in plane |
1055 | m | 1068 | 55.76 | 1107 | 34.71 | νN–N |
974 | w | 989 | 1.56 | 1009 | 1.44 | C–H C–H out of plane |
846 | w | 851 | 35.56 | 859 | 31.32 | C–H |
813 | m | 836 | 16.82 | 843 | 22.38 | C–H |
750 | w | 775 | 50.37 | 785 | 69.11 | C–H |
524 | w | 464 | 7.80 | 467 | 7.94 | C–H |
2.3. Orbital Analysis
3. Experimental, Theoretical and Computational Methods
3.1. General
3.2. Preparation of N'-(4-Dimethylaminobenzylidene)isonicotinohydrazide Monohydrate
3.3. X-ray Crystallography
3.4. Computational Methods
4. Conclusions
Supplementary Materials
Supplementary Materials
Supplementary File 1References
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Sahebalzamani, H.; Khaligh, N.; Ghammamy, S.; Salimi, F.; Mehrani, K. Crystal Structure and Density Functional Theory Study on Structural Properties and Energies of a Isonicotinohydrazide Compound. Molecules 2011, 16, 7715-7724. https://doi.org/10.3390/molecules16097715
Sahebalzamani H, Khaligh N, Ghammamy S, Salimi F, Mehrani K. Crystal Structure and Density Functional Theory Study on Structural Properties and Energies of a Isonicotinohydrazide Compound. Molecules. 2011; 16(9):7715-7724. https://doi.org/10.3390/molecules16097715
Chicago/Turabian StyleSahebalzamani, Hajar, Nina Khaligh, Shahriar Ghammamy, Farshid Salimi, and Kheyrollah Mehrani. 2011. "Crystal Structure and Density Functional Theory Study on Structural Properties and Energies of a Isonicotinohydrazide Compound" Molecules 16, no. 9: 7715-7724. https://doi.org/10.3390/molecules16097715