Synthesis, X-ray Structure, Hirshfeld Analysis of Biologically Active Mn(II) Pincer Complexes Based on s-Triazine Ligands
Abstract
:1. Introduction
2. Materials and Methods
2.1. Preparation of the Organic Ligands
2.2. Syntheses of [Mn(MorphBPT)(H2O)2NO3]NO3; (1) and [Mn(PipBPT)(H2O)2NO3]NO3; (2)
2.3. Crystal Structure Determination
2.4. Antimicrobial Studies
2.5. Density Functional Theory (DFT) Calculations
3. Results and Discussion
3.1. X-ray Crystal Structure Description
3.2. Analysis of Molecular Packing
3.3. AIM Topology Analysis
3.4. Antimicrobial Activity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Compound | 1 | 2 |
---|---|---|
Empirical formula | C17H26MnN10O9 | C18H28MnN10O8 |
Formula weight (g/mol) | 569.42 | 567.44 |
Temperature (K) | 124(2) | 117(2) |
λ (Mo-Kα, Å) | 0.71073 | 0.71073 |
Crystal system | Triclinic | Triclinic |
Space group | P-1 | P-1 |
Unit cell dimensions | a = 8.2794(5) Å | a = 7.830(5) Å |
b = 12.1167(7) Å | b = 12.951(7) Å | |
c = 12.1738(7) Å | c = 13.990(7) Å | |
α = 88.3660(19)° | α = 116.533(10)° | |
β = 89.605(2)° | β = 94.832(14)° | |
γ = 79.184(2)° | γ = 101.694(16)° | |
Volume (Å3) | 1199.08(12) | 1217.9(12) |
Z | 2 | 2 |
Density (calc. g/cm3) | 1.577 | 1.547 |
Absorption coefficient (mm−1) | 0.621 | 0.608 |
F(000) | 590 | 590 |
Crystal size (mm3) | 0.29 × 0.21 × 0.11 | 0.31 × 0.23 × 0.19 |
θ range for data collection | 2.36 to 26.34° | 2.71 to 25.31° |
Index ranges | −10 ≤ h ≤ 10, −15 ≤ k ≤ 15, −15 ≤ l ≤ 15 | −9 ≤ h ≤ 9, −15 ≤ k ≤ 15, −16 ≤ l ≤ 16 |
Reflections collected | 21,451 | 19,570 |
Independent reflections | 4863 [R(int) = 0.0315] | 4437 [R(int) = 0.0554] |
Completeness to θ | 99.30% | 99.80% |
Refinement method | Full-matrix least-squares on F2 | |
Data/restraints/parameters | 4863/0/385 | 4437/0/351 |
Goodness-of-fit on F2 | 0.894 | 1.06 |
Final R indices [I>2sigma(I)] | R1 = 0.0275, wR2 = 0.0671 | R1 = 0.0298, wR2 = 0.0732 |
R indices (all data) | R1 = 0.0341, wR2 = 0.0721 | R1 = 0.0371, wR2 = 0.0775 |
Extinction coefficient | 0.0100(8) | 0.0157(17) |
Largest diff. peak and hole | 0.371 and −0.318 | 0.409 and −0.308 |
CCDC | 2025609 | 2025610 |
Atoms | 1 | 2 |
---|---|---|
Mn1–O2 | 2.1416(12) | 2.1288(19) |
Mn1–O3 | 2.1683(11) | 2.1604(16) |
Mn1–O1 | 2.2159(12) | 2.2306(17) |
Mn1–N5 | 2.2172(12) | 2.1973(18) |
Mn1–N1 | 2.3188(13) | 2.3097(19) |
Mn1–N7 | 2.3267(13) | 2.3580(18) |
O2–Mn1–O3 | 90.35(5) | 96.78(6) |
O2–Mn1–O1 | 80.70(5) | 83.33(6) |
O3–Mn1–O1 | 167.76(5) | 172.64(5) |
O2–Mn1–N5 | 170.23(5) | 166.35(6) |
O3–Mn1–N5 | 97.55(4) | 94.69(6) |
O1–Mn1–N5 | 90.62(5) | 84.34(6) |
O2–Mn1–N1 | 115.16(5) | 116.12(6) |
O3–Mn1–N1 | 98.37(5) | 94.40(6) |
O1–Mn1–N1 | 93.02(5) | 92.13(6) |
N5–Mn1–N1 | 69.49(4) | 70.18(5) |
O2–Mn1-N7 | 106.03(5) | 103.93(6) |
O3–Mn1–N7 | 85.47(4) | 86.40(6) |
O1–Mn1–N7 | 88.98(5) | 86.44(6) |
N5–Mn1–N7 | 69.09(4) | 69.39(5) |
N1–Mn1–N7 | 138.55(4) | 139.49(6) |
Atoms | D–H (Å) | H···A (Å) | D···A (Å) | D–H···A (°) |
---|---|---|---|---|
1 | ||||
O2–H1···O11 | 0.82(2) | 1.89(2) | 2.662(3) | 157(2) |
O2–H1···O12 | 0.82(2) | 1.95(2) | 2.766(3) | 175(2) |
O1–H14···O9 | 0.83(2) | 1.97(2) | 2.728(3) | 153(2) |
O1–H14···O7i | 0.83(2) | 1.96(2) | 2.758(3) | 161(2) |
O1–H16···O10 | 0.85(2) | 2.07(2) | 2.884(3) | 161(2) |
O1–H16···O11 | 0.85(2) | 2.07(2) | 2.831(4) | 150(2) |
O2–H21···O5 | 0.85(2) | 2.54(2) | 2.924(2) | 109(2) |
O2–H21···O4ii | 0.85(2) | 2.01(2) | 2.816(2) | 159(2) |
C3–H3···O3iii | 0.95 | 2.52 | 3.319(2) | 142 |
C9–H9A···O7iv | 0.98 | 2.49 | 3.455(3) | 170 |
C11–H11···O7v | 0.95 | 2.39 | 3.328(3) | 171 |
C13–H13C···O10 | 0.98 | 2.49 | 3.271(3) | 136 |
Symmetry Code: (i) 1-x,1-y,2-z; (ii) -x,2-y,1-z; (iii) 1+x,y,z; (iv) -1+x,y,z; (v) -x,1-y,2-z | ||||
2 | ||||
O1–H1A···O7i | 0.83(3) | 2.04(3) | 2.839(3) | 162(3) |
O1–H1B···O7 | 0.86(2) | 1.89(2) | 2.723(3) | 163(2) |
O2–H2A···O6 | 0.87(2) | 1.92(2) | 2.758(3) | 161(2) |
O2–H2B···O4ii | 0.83(4) | 1.99(4) | 2.795(3) | 162(4) |
C3–H3···O3iii | 0.95 | 2.53 | 3.240(3) | 132 |
C9–H9C···O8iv | 0.98 | 2.42 | 3.329(3) | 154 |
Symmetry Code: (i) 1-x,1-y,-z; (ii) 1-x,1-y,1-z; (iii) 1+x,y,z; (iv) -x,1-y,-z |
1 | 2 | ||
---|---|---|---|
C7···O8i | 2.940(3) | C8···O7ii | 3.090(2) |
N3···O8i | 3.077(3) | C7···O8ii | 2.982(2) |
N4···O8i | 2.995(3) | ||
C8···O8i | 3.044(3) | ||
C6···O8i | 3.141(3) | ||
C6···O9i | 3.052(3) | ||
N5···O9i | 2.831(3) | ||
C8···O9i | 2.889(3) | ||
Symmetry Code: (i) x,y,z in 1 (ii) 1-x,1-y,-z in 2 |
Bond | Ρ(r) | G(r) | V(r) | Eint a | H(r) b | V(r)/G(r) c |
---|---|---|---|---|---|---|
1 (MPW1PW91) | ||||||
Mn1–N1 | 0.0315 | 0.0526 | −0.0511 | 16.0302 | 0.0015 | 0.9712 |
Mn1–N7 | 0.0310 | 0.0508 | −0.0495 | 15.5195 | 0.0013 | 0.9737 |
Mn1–N5 | 0.0446 | 0.0730 | −0.0749 | 23.5085 | −0.0019 | 1.0257 |
Mn1–O1 | 0.0348 | 0.0617 | −0.0602 | 18.8813 | 0.0015 | 0.9754 |
Mn1–O2 | 0.0423 | 0.0764 | −0.0759 | 23.8078 | 0.0006 | 0.9927 |
Mn1–O3 | 0.0392 | 0.0731 | −0.0719 | 22.5571 | 0.0012 | 0.9835 |
1 (WB97XD) | ||||||
Mn1–N1 | 0.0315 | 0.0524 | −0.0507 | 15.9153 | 0.0016 | 0.9689 |
Mn1–N7 | 0.0309 | 0.0506 | −0.0491 | 15.4165 | 0.0014 | 0.9714 |
Mn1–N5 | 0.0445 | 0.0729 | −0.0746 | 23.3928 | −0.0017 | 1.0234 |
Mn1–O1 | 0.0347 | 0.0615 | −0.0599 | 18.7798 | 0.0016 | 0.9734 |
Mn1–O2 | 0.0422 | 0.0763 | −0.0755 | 23.6955 | 0.0007 | 0.9904 |
Mn1–O3 | 0.0392 | 0.0728 | −0.0715 | 22.4445 | 0.0013 | 0.9820 |
2 (MPW1PW91) | ||||||
Mn1–N1 | 0.0323 | 0.0536 | −0.0522 | 16.3859 | 0.0014 | 0.9746 |
Mn1–N7 | 0.0285 | 0.0464 | −0.0449 | 14.0784 | 0.0016 | 0.9662 |
Mn1–N5 | 0.0465 | 0.0774 | −0.0796 | 24.9777 | −0.0022 | 1.0283 |
Mn1–O1 | 0.0339 | 0.0592 | −0.0574 | 17.9982 | 0.0018 | 0.9698 |
Mn1–O2 | 0.0446 | 0.0815 | −0.0810 | 25.4111 | 0.0005 | 0.9940 |
Mn1–O3 | 0.0404 | 0.0754 | −0.0743 | 23.3263 | 0.0010 | 0.9862 |
2 (WB97XD) | ||||||
Mn1–N1 | 0.0323 | 0.0533 | −0.0518 | 16.2604 | 0.0015 | 0.9724 |
Mn1–N7 | 0.0284 | 0.0462 | −0.0445 | 13.9667 | 0.0017 | 0.9638 |
Mn1–N5 | 0.0464 | 0.0772 | −0.0792 | 24.8540 | −0.0020 | 1.0260 |
Mn1–O1 | 0.0338 | 0.0590 | −0.0570 | 17.8993 | 0.0019 | 0.9676 |
Mn1–O2 | 0.0445 | 0.0812 | −0.0806 | 25.2873 | 0.0006 | 0.9921 |
Mn1–O3 | 0.0404 | 0.0751 | −0.0740 | 23.2066 | 0.0012 | 0.9846 |
Bond | MPW1PW91 | WB97XD | MPW1PW91 | WB97XD |
---|---|---|---|---|
1 | 2 | |||
Mn1–N1 | 0.143 | 0.144 | 0.142 | 0.143 |
Mn1–N7 | 0.136 | 0.137 | 0.122 | 0.123 |
Mn1–N5 | 0.198 | 0.199 | 0.206 | 0.207 |
Mn1–O1 | 0.129 | 0.129 | 0.119 | 0.119 |
Mn1–O2 | 0.163 | 0.163 | 0.170 | 0.171 |
Mn1–O3 | 0.157 | 0.158 | 0.159 | 0.161 |
Atom | MorphBPT | 1 | PipBPT | 2 |
---|---|---|---|---|
N5 | −0.4618(−0.4740) | −0.5921(−0.6022) | −0.4671(−0.4794) | −0.5892(−0.5987) |
N1 | −0.2237(−0.2271) | −0.3163(−0.3191) | −0.2243(−0.2275) | −0.3042(−0.3069) |
N7 | −0.2015(−0.2275) | −0.3084(−0.3106) | −0.2224(−0.2256) | −0.3085(−0.3114) |
Compound | S. aureus | E. coli | C. albicans |
---|---|---|---|
MorphBPT | - | - | - |
PipBPT | 11 | - | 12 |
1 | 21 | 17 | 15 |
2 | 27 | 20 | 17 |
Fluconazole | - | - | 14 |
Gentamycin | 28 | 21 | - |
Microbes | 1 | 2 | ||
---|---|---|---|---|
MIC (µg/mL) | MBC (µg/mL) | MIC (µg/mL) | MBC (µg/mL) | |
S. aureus | 8.3 | 16.5 | 6.5 | 13.5 |
E. coli | 8.3 | 16.5 | 8.3 | 16.8 |
C. albicans | 18.5 | 100 | 18.5 | 100 |
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Soliman, S.M.; Al-Rasheed, H.H.; El-Faham, A. Synthesis, X-ray Structure, Hirshfeld Analysis of Biologically Active Mn(II) Pincer Complexes Based on s-Triazine Ligands. Crystals 2020, 10, 931. https://doi.org/10.3390/cryst10100931
Soliman SM, Al-Rasheed HH, El-Faham A. Synthesis, X-ray Structure, Hirshfeld Analysis of Biologically Active Mn(II) Pincer Complexes Based on s-Triazine Ligands. Crystals. 2020; 10(10):931. https://doi.org/10.3390/cryst10100931
Chicago/Turabian StyleSoliman, Saied M., Hessa H. Al-Rasheed, and Ayman El-Faham. 2020. "Synthesis, X-ray Structure, Hirshfeld Analysis of Biologically Active Mn(II) Pincer Complexes Based on s-Triazine Ligands" Crystals 10, no. 10: 931. https://doi.org/10.3390/cryst10100931