Fe(III) Complexes Based on Mono- and Bis-pyrazolyl-s-triazine Ligands: Synthesis, Molecular Structure, Hirshfeld, and Antimicrobial Evaluations
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure Description
2.1.1. Crystal Structure Description of [Fe(PipBPT)Cl2][FeCl4] (1)
2.1.2. Crystal Structure Description of [Fe(MorphBPT)Cl2][FeCl4] (2)
2.1.3. Crystal Structure Description of [H(bisMorphPT)][FeCl4] bisMorphPT.2H2O (3)
2.2. Analysis of Molecular Packing
2.3. Antimicrobial Activity of the Studied Compounds
2.3.1. Inhibition Zones
2.3.2. Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC)
3. Experimental
3.1. Materials and Physical Measurements
3.2. Syntheses
3.2.1. Synthesis of s-Triazine-Based Ligands
3.2.2. Synthesis of Fe(III) Complexes
3.3. Crystal Structure Determination
3.4. Antimicrobial Studies
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | 1 | 2 | 3 |
---|---|---|---|
Empirical formula | C18H24Cl6Fe2N8 | C17H22Cl6Fe2N8O | C32H51Cl4FeN14O6 |
Formula weight (g/mol) | 676.85 | 678.82 | 925.51 |
Temperature (K) | 119(2) | 124(2) | 293(2) |
λ (Å) | 0.71073 | 0.71073 | 0.71073 |
Crystal system | Monoclinic | Orthorhombic | Triclinic |
Space group | P21/c | Pbcm | P-1 |
Unit cell dimensions | |||
a (Å) | 8.9549(3) | 8.5201(3) | 12.4352(15) |
b (Å) | 15.7871(6) | 13.7094(5) | 12.8632(16) |
c (Å) | 19.9063(7) | 23.2383(9) | 15.6509(19) |
α (°) | 90 | 90 | 76.955(3) |
β (°) | 99.457(2) | 90 | 89.531(3) |
γ (°) | 90 | 90 | 66.926(3) |
Volume (Å3) | 2775.9(2) | 2714.4(2) | 2234.7(5) |
Z | 4 | 4 | 2 |
Density (calculated, g/cm3) | 1.620 | 1.661 | 1.370 |
Absorption coefficient (mm−1) | 1.647 | 1.687 | 0.633 |
F(000) | 1368 | 1368 | 958 |
Crystal size (mm3) | 0.29 × 0.16 × 0.09 | 0.04 × 0.12 × 0.15 | 0.26 × 0.20 × 0.08 |
θ range (°) | 2.31 to 25.49 | 2.81 to 24.99 | 2.33 to 25.09 |
Index ranges | −10 ≤ h ≤ 10, −19 ≤ k ≤ 19, −24 ≤ l ≤ 24 | −10 ≤ h ≤ 10, −16 ≤ k ≤ 16, −27 ≤ l ≤ 27 | −14 ≤ h ≤ 14, −15 ≤ k ≤ 15, −18 ≤ l ≤ 18 |
Reflections collected | 38,064 | 21,560 | 64,462 |
Independent reflections | 5139 [R(int) = 0.0427] | 2453 [R(int) = 0.0294] | 7915 [R(int) = 0.0769] |
Completeness to theta (%) | 99.8 | 99.90 | 99.5 |
Refinement method | Full-matrix least-squares on F2 | ||
Data/restraints/parameters | 5139/0/311 | 2453/0/207 | 7909/0/528 |
Goodness-of-fit on F2 | 1.045 | 1.083 | 1.008 |
Final R indices [I > 2sigma(I)] | R1 = 0.0238, wR2 = 0.0530 | R1 = 0.0397, wR2 = 0.0988 | R1 = 0.0932, wR2 = 0.2007 |
R indices (all data) | R1 = 0.0334, wR2 = 0.0571 | R1 = 0.0440, wR2 = 0.1024 | R1 = 0.1654, wR2 = 0.2464 |
Largest diff. peak and hole | 0.291 and −0.306 | 0.621 and −1.035 | 0.87and −0.64 |
CCDC No. | 2044018 | 2044016 | 2044017 |
Atoms | Distance (Å) | Atoms | Distance (Å) |
Fe1-N1 | 2.0295(15) | Fe2-Cl3 | 2.1840(6) |
Fe1-N3 | 2.0940(16) | Fe2-Cl4 | 2.1836(6) |
Fe1-N2 | 2.1092(16) | Fe2-Cl5 | 2.1791(6) |
Fe1-Cl1 | 2.1699(6) | Fe2-Cl6 | 2.1873(6) |
Fe1-Cl2 | 2.1766(6) | ||
Atoms | Angle (°) | Atoms | Angle (°) |
N1-Fe1-N3 | 73.24(6) | N2-Fe1-Cl1 | 100.76(5) |
N1-Fe1-N2 | 73.65(6) | N1-Fe1-Cl2 | 133.34(5) |
N3-Fe1-N2 | 146.46(6) | N3-Fe1-Cl2 | 99.11(5) |
N1-Fe1-Cl1 | 117.06(5) | N2-Fe1-Cl2 | 99.58(5) |
N3-Fe1-Cl1 | 98.84(5) | Cl1-Fe1-Cl2 | 109.58(3) |
Atoms | D-H (Å) | H…A (Å) | D…A (Å) | D-H…A (°) |
---|---|---|---|---|
Complex 1 | ||||
C3-H3…Cl3 i | 0.95 | 2.77 | 3.622(2) | 149 |
C5-H5B…Cl6 i | 0.98 | 2.8 | 3.723(2) | 158 |
C8-H8…Cl1ii | 0.95 | 2.78 | 3.428(2) | 126 |
i 1 + x,y,z i 1 + x,y,z ii 1-x,-y,1-z and | ||||
Complex 2 | ||||
C5-H5…Cl4A i | 0.95 | 2.79 | 3.651(5) | 152 |
C9A-H9A1…Cl1A ii | 0.99 | 2.55 | 2.916(7) | 101 |
i x,-1 + y,z and ii 1-x,1/2 + y,3/2-z |
Atoms | Distance (Å) | Atoms | Distance (Å) |
Fe1-N1 | 2.038(3) | Fe2-Cl4B | 2.085(3) |
Fe1-N2 1 | 2.099(3) | Fe2-Cl3 2 | 2.1667(10) |
Fe1-N2 | 2.099(3) | Fe2-Cl3 | 2.1668(10) |
Fe1-Cl1A | 2.250(3) | Fe2-Cl4A | 2.329(3) |
Fe1-Cl2A | 2.262(5) | ||
Fe1-Cl1B | 2.151(2) | ||
Fe1-Cl2B | 2.090(6) | ||
Atoms | Angle (°) | Atoms | Angle (°) |
N1-Fe1-N2 1 | 73.66(7) | Cl2B-Fe1-N2 | 101.82(8) |
N1-Fe1-N2 | 73.66(7) | N1-Fe1-Cl1B | 149.41(12) |
N2 1-Fe1-N2 | 146.19(13) | Cl2B-Fe1-Cl1B | 90.49(17) |
N1-Fe1-Cl1A | 130.50(12) | N2 1-Fe1-Cl1B | 101.81(7) |
N21-Fe1-Cl1A | 97.28(7) | N2-Fe1-Cl1B | 101.81(7) |
N2-Fe1-Cl1A | 97.28(7) | Cl1A-Fe1-Cl2A | 122.17(15) |
N1-Fe1-Cl2A | 107.33(16) | Cl4B-Fe2-Cl3 2 | 106.87(8) |
N2 1-Fe1-Cl2A | 98.86(8) | Cl4B-Fe2-Cl3 | 120.70(11) |
N2-Fe1-Cl2A | 98.86(8) | Cl32-Fe2-Cl3 | 109.97(6) |
N1-Fe1-Cl2B | 120.10(17) | Cl32-Fe2-Cl4A | 105.43(8) |
Cl2B-Fe1-N2 1 | 101.82(8) | Cl3-Fe2-Cl4A | 102.31(10) |
Test Compounds | Microbes | ||||
---|---|---|---|---|---|
Staphylococcus aureus | Staphylococcus epidermidis | Escherichia coli | Pseudomonas aeruginosa | Candida albicans | |
PipBPT | 11 | 17 | - | 13 | 12 |
MorphBPT | - | - | - | - | - |
bisMorphPT | - | - | - | - | - |
1 | 25 | 23 | 19 | 22 | 18 |
2 | 18 | 19 | 16 | 17 | 14 |
3 | 17 | 16 | 14 | 15 | 12 |
Fluconazole | - | - | - | - | 14 |
Gentamycin | 28 | 22 | 21 | 19 | - |
Compounds | Organism | Concentration | ||
---|---|---|---|---|
100 | 200 | 300 | ||
1 | E. coli | 16 | 19 | 21 |
P. aeruginosa | 20 | 22 | 23 | |
S. aureus | 19 | 25 | 26 | |
S. epidermidis | 18 | 23 | 25 | |
C. albicans | 14 | 18 | 20 | |
PipBPT | E. coli | - | - | - |
P. aeruginosa | 13 | 15 | 18 | |
S. aureus | 17 | 18 | 19 | |
S. epidermidis | 11 | 13 | 15 | |
C. albicans | 10 | 11 | 13 | |
2 | E. coli | 14 | 16 | 18 |
P. aeruginosa | 14 | 17 | 18 | |
S. aureus | 14 | 18 | 19 | |
S. epidermidis | 15 | 19 | 20 | |
C. albicans | 12 | 14 | 16 | |
3 | E. coli | 12 | 15 | 17 |
P. aeruginosa | 12 | 15 | 17 | |
S. aureus | 14 | 17 | 19 | |
S. epidermidis | 13 | 16 | 17 | |
C. albicans | 11 | 12 | 15 |
Microbes | [Fe(PipBPT)Cl2][FeCl4] (1) | [Fe(MorphBPT)Cl2][FeCl4] (2) | [H(bisMorphPT)][FeCl4]. bisMorphPT (3) | |||
---|---|---|---|---|---|---|
MIC | MBC | MIC | MBC | MIC | MBC | |
S. epidermidis | 8.3 | 16.6 | 9.7 | 19.4 | 18.8 | 37.5 |
S. aureus | 8.7 | 17.5 | 9.8 | 19.6 | 18.8 | 37.5 |
E. coli | 8.7 | 17.5 | 9.8 | 19.6 | 18.8 | 37.5 |
P. aeruginosa | 8.2 | 16.5 | 9.8 | 19.6 | 18.8 | 37.5 |
C. albicans | 18.8 | 100.0 | 37.5 | 150.0 | 37.5 | 150.0 |
Sample Availability: Samples of the compounds are available from the authors. |
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Soliman, S.M.; Al-Rasheed, H.H.; Albering, J.H.; El-Faham, A. Fe(III) Complexes Based on Mono- and Bis-pyrazolyl-s-triazine Ligands: Synthesis, Molecular Structure, Hirshfeld, and Antimicrobial Evaluations. Molecules 2020, 25, 5750. https://doi.org/10.3390/molecules25235750
Soliman SM, Al-Rasheed HH, Albering JH, El-Faham A. Fe(III) Complexes Based on Mono- and Bis-pyrazolyl-s-triazine Ligands: Synthesis, Molecular Structure, Hirshfeld, and Antimicrobial Evaluations. Molecules. 2020; 25(23):5750. https://doi.org/10.3390/molecules25235750
Chicago/Turabian StyleSoliman, Saied M., Hessa H. Al-Rasheed, Jörg H. Albering, and Ayman El-Faham. 2020. "Fe(III) Complexes Based on Mono- and Bis-pyrazolyl-s-triazine Ligands: Synthesis, Molecular Structure, Hirshfeld, and Antimicrobial Evaluations" Molecules 25, no. 23: 5750. https://doi.org/10.3390/molecules25235750