Multidimensional Transition Metal Complexes Based on 3-Amino-1H-1,2,4-triazole-5-carboxylic Acid: From Discrete Mononuclear Complexes to Layered Materials
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
- (i)
- the use NaOH or triethylamine (Et3N) to deprotonate H2atrc in reactions with transition metal salts (such as Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+ and Cd2+) led to poor crystalline powders;
- (ii)
- the use of temperatures above 60 °C in the reactions with the aforementioned metals also led to the formation of microcrystalline powders;
- (iii)
- with the use of less than ca. 6 mL of water in the systems mixed crystals of the new materials and the parent H2atrc ligand were easily produced;
- (iv)
- with 30 min of stirring, the clear mixed solutions become cloudy and no pure single crystals were produced.
2.2. Mononuclear Complexes
1 | 2 | Ref [34] | |||
---|---|---|---|---|---|
Zn1–O1W | 1.975(5) | Mn1–O1W | 2.206(2) | Cd1–O3 | 2.384(2) |
Zn1–N14 | 1.981(3) | Mn1–N14 | 2.239(3) | Cd1–N1 | 2.255(3) |
Zn1–O12 | 2.171(3) | Mn1–O1 | 2.186(2) | Cd1–O1 | 2.345(2) |
N14–Zn1–O12 | 79.57(12) | O1–Mn1–N14 | 76.23(8) | O1–Cd1–N1 | 73.14(5) |
O12–Zn1–O12 a | 168.94(17) | O1–Mn1–O1 b | 180.0 | ||
O1W–Zn1–O12 | 95.53(9) | O1–Mn1–O1W | 87.38(8) | ||
N14–Zn1–N14 a | 131.5(2) | N14–Mn1–N14 b | 180.0 | ||
O1W–Zn1–N14 | 114.25(11) | O1W–Mn1–N14 | 90.44(8) | ||
O1–Mn1–N14 b | 103.77(8) | ||||
O1–Mn1–O1W b | 92.62(8) | ||||
O1W–Mn1–N14 b | 89.56(9) | ||||
O1W–Mn1–O1W b | 180.0 |
D–H···A | D···A/Å | <DHA/° | |
---|---|---|---|
1 | N11–H11A···O11 c | 2.749(4) | 171 |
N1–H1A···O12 a | 3.191(5) | 141 | |
N1–H1A···O1W d | 3.322(4) | 144 | |
N1–H1A···N12 c | 2.964(5) | 167 | |
O1W–H1WA···O11 e | 2.781(3) | 158 | |
O1W–H1WA···O12 e | 3.031(3) | 131 | |
2 | N11–H11A···O2W f | 2.820(3) | 142 |
N12–H12A···O2W g | 2.957(5) | 116 | |
N1–H1A···O1W h | 2.957(4) | 173 | |
N1–H1B···O2W f | 3.115(4) | 142 | |
N1–H1B···O2W h | 3.141(4) | 128 | |
O1W–H1WA···O1 i | 2.689(3) | 160 | |
O1W–H1WB···O2 j | 2.639(3) | 162 | |
O2W–H2WB···O2 j | 2.757(3) | 175 | |
O2W–H2WA···N12 k | 2.959(3) | 152 |
3 | 4 | 5 | |||
---|---|---|---|---|---|
Fe1–O5 | 1.949(2) | Cd1–N24 | 2.239(5) | Mn1–N12 n | 2.192(2) |
Fe1–O5 l | 1.979(2) | Cd1–N14 | 2.299(5) | Mn1–O1W | 2.194(2) |
Fe1–O4 | 2.030(2) | Cd1–O3 | 2.344(5) | Mn1–O1 | 2.2179(19) |
Fe1–O1 | 2.041(3) | Cd1–O4 m | 2.397(4) | Mn1–O2 o | 2.2531(19) |
Fe1–N14 | 2.096(3) | Cd1–O1W | 2.407(5) | Mn1–N11 o | 2.255(2) |
Fe1–N24 | 2.113(3) | Cd1–O2 | 2.434(4) | Mn1–N14 | 2.299(2) |
Cd1–O3 m | 2.593(4) | ||||
O5–Fe1–O5 l | 76.37(10) | N24–Cd1–N14 | 125.39(19) | N12 n–Mn1–O1W | 88.23(8) |
O5–Fe1–O4 | 165.65(10) | N24–Cd1–O3 | 73.44(17) | N12 n–Mn1–O1 | 100.41(8) |
O5–Fe1–O1 | 92.88(10) | N24–Cd1–O4 m | 140.30(17) | N12 n–Mn1–O2 o | 168.57(8) |
O5–Fe1–N14 | 97.93(10) | N24–Cd1–O1W | 88.15(19) | N12 n–Mn1–N11 o | 97.87(8) |
O5–Fe1–N24 | 97.79(10) | N24–Cd1–O2 | 87.70(17) | N12 n–Mn1–N14 | 94.18(8) |
O5 l–Fe1–O4 | 90.56(10) | N24–Cd1–O3 m | 87.73(17) | O1W–Mn1–O1 | 94.82(7) |
O5 l–Fe1–O1 | 164.41(10) | N14–Cd1–O3 | 88.21(18) | O1W–Mn1–O2 o | 83.68(7) |
O5 l–Fe1–N14 | 92.25(11) | N14–Cd1–O4 m | 85.21(17) | O1W–Mn1–N11 o | 98.93(8) |
O5 l–Fe1–N24 | 95.89(11) | N14–Cd1–O1W | 137.85(19) | O1W–Mn1–N14 | 170.92(9) |
O4–Fe1–O1 | 101.08(10) | N14–Cd1–O2 | 70.68(17) | O1–Mn1–O2 o | 88.34(7) |
O4–Fe1–N14 | 88.36(10) | N14–Cd1–O3 m | 127.60(17) | O1–Mn1–N11 o | 157.40(8) |
O4–Fe1–N24 | 77.40(10) | O3–Cd1–O4 m | 138.78(15) | O1–Mn1–N14 | 76.15(8) |
O1–Fe1–N14 | 77.89(11) | O3–Cd1–O1W | 77.05(17) | O2 o–Mn1–N11 o | 75.53(8) |
O1–Fe1–N24 | 96.75(11) | O3–Cd1–O2 | 135.96(16) | O2 o–Mn1–N14 | 95.06(8) |
N14–Fe1–N24 | 163.63(11) | O3–Cd1–O3 m | 143.57(3) | N11 o–Mn1–N14 | 89.42(8) |
O4 m–Cd1–O1W | 80.97(16) | ||||
O4 m–Cd1–O2 | 79.08(15) | ||||
O4 m–Cd1–O3 m | 52.60(14) | ||||
O1W–Cd1–O2 | 143.05(16) | ||||
O1W–Cd1–O3 m | 71.32(16) | ||||
O2–Cd1–O3 m | 71.83(15) |
2.3. Binuclear Complex
D–H···A | D···A/Å | <DHA/° | D–H···A | D···A/Å | <DHA/° |
---|---|---|---|---|---|
N11–H11A···O2W | 2.746(4) | 171 | O1W–H1WA···O3Wu | 2.847(4) | 174 |
N1–H1A···O3W p | 2.905(4) | 151 | O1W–H1WB···N22t | 2.914(4) | 179 |
N1–H1B···O2 q | 3.023(4) | 173 | O2W–H2WA···O1Wv | 2.678(4) | 154 |
N21–H21A···O2W r | 2.903(4) | 135 | O2W–H2WB···O2 q | 2.842(4) | 145 |
N21–H21A···O1 s | 2.866(4) | 128 | O3W–H3WA···O4 | 2.719(3) | 166 |
N2–H2A···O3 t | 2.914(4) | 163 | O3W–3WB···N12 k | 2.830(4) | 175 |
N2–H2B···O1W | 2.872(4) | 154 | O5–H5A···O3 t | 2.829(3) | 159 |
2.4. One-Dimensional Chain (1D)
D–H···A | D···A/Å | <DHA/° | D–H···A | D···A/Å | <DHA/° | ||
---|---|---|---|---|---|---|---|
4 | N11–H11A···O4 w | 2.769(7) | 169 | 5 | N1–H1A···O A | 2.966(3) | 156 |
N1–H1A···O1W x | 3.200(8) | 162 | N1–H1B···O1W f | 3.224(3) | 151 | ||
N1–H1B···N22 w | 3.211(8) | 153 | O1W–H1WA···O2 b | 2.748(3) | 161 | ||
N21–H21A···O1 y | 2.684(6) | 164 | O1W–H1WB···O2W B | 2.714(3) | 152 | ||
N2–H2A···O1W m | 3.064(8) | 155 | O2W–H2WB···N1 | 2.872(3) | 160 | ||
N2–H2B···N12 y | 3.037(8) | 158 | O2W–H2WA···N14 C | 3.186(3) | 138 | ||
O1W–H1WB···O1 z | 2.747(7) | 165 | O2W–H2WA···N12 D | 3.183(3) | 129 | ||
O1W–H1WA···O2 x | 2.698(7) | 158 | O2W–H2WA···N11 D | 3.159 (3) | 121 |
2.5. Coordination Layer (2D)
3. Experimental Section
3.1. Materials and Methods
3.2. Synthesis
3.3. Single Crystal X-ray Diffraction
1 | 2 | 3 | 4 | 5 | |
---|---|---|---|---|---|
Empirical formula | C6H8N8O5Zn | C6H14MnN8O8 | C12H26Fe2N16O16 | C6H8CdN8O5 | C3H6MnN4O4 |
Color and Habit | Colorless Plate | Colorless block | Orange block | Colorless block | Colorless block |
Crystal Size (mm3) | 0.42 × 0.21 × 0.07 | 0.08 × 0.04 × 0.03 | 0.07 × 0.02 × 0.02 | 0.07 × 0.03 × 0.04 | 0.12 × 0.11 × 0.05 |
Crystal system | Orthorhombic | Triclinic | Orthorhombic | Monoclinic | Monoclinic |
Space group | Pbcn | Pī | Pnna | P21/n | P21/c |
a (Ǻ) | 9.537(3) | 5.2482(9) | 27.111(6) | 8.9893(13) | 8.1472(6) |
b Ǻ | 6.865(2) | 6.5330(11) | 12.697(3) | 8.9785(13) | 9.9846(7) |
c (Ǻ) | 17.120(5) | 10.6128(18) | 7.7352(17) | 13.9642(16) | 9.3679(6) |
α (°) | 90 | 90.532(10) | 90 | 90 | 90 |
β (°) | 90 | 102.774(11) | 90 | 108.117(5) | 113.994(4) |
γ (°) | 90 | 109.139(10) | 90 | 90 | 90 |
V (Ǻ3) | 1120.8(6) | 333.93(10) | 2662.6(11) | 1071.2(3) | 696.20(8) |
Z | 4 | 2 | 4 | 4 | 4 |
Dc (Mg m−3) | 2.000 | 1.896 | 1.901 | 2.385 | 2.071 |
μ (mm−1) | 2.232 | 1.052 | 1.197 | 2.081 | 1.877 |
F (000) | 680 | 195 | 1560 | 752 | 436 |
θ (°) | 3.66 to 26.37 | 4.01 to 29.46 | 3.41 to 25.35 | 3.07 to 25.02 | 2.74 to 26.37 |
Data completeness | |||||
Reflections measured | 8019 | 5074 | 12255 | 13793 | 7382 |
Independent reflections | 1146 (Rint = 0.0331) | 1055 (Rint = 0.0411) | 2418 (Rint = 0.0652) | 1878 (Rint = 0.0512) | 1418(Rint = 0.1497) |
Final R1, wR2 [I > 2σ(I)] | 0.0393, 0.0867 | 0.0514, 0.0828 | 0.0436, 0.0807 | 0.0432, 0.1128 | 0.0388, 0.0896 |
R1, wR2 (all data) | 0.0568, 0.0944 | 0.0603, 0.0857 | 0.087, 0.0925 | 0.0481, 0.1150 | 0.0474, 0.0935 |
Δρmax/min (eǺ−3) | 0.389, −0.555 | 0.384, −0.487 | 0.364, −0.433 | 0.729, −0.974 | 0.555, −0.569 |
Δρmax/(eǺ−3) | Distance/Ǻ | from | Δρmin/(eǺ−3) | Distance/Ǻ | from | |
---|---|---|---|---|---|---|
1 | 0.389 | 0.85 | O1W | −0.555 | 0.70 | Zn1 |
2 | 0.384 | 1.17 | Mn1 | −0.487 | 0.61 | Mn1 |
3 | 0.364 | 0.52 | N24 | −0.433 | 0.64 | Fe1 |
4 | 0.729 | 0.63 | O3 | −0.974 | 1.29 | H1A |
5 | 0.555 | 0.90 | Mn1 | −0.569 | 0.96 | Mn1 |
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Liu, B.; Fernandes, J.A.; Tomé, J.P.C.; Paz, F.A.A.; Cunha-Silva, L. Multidimensional Transition Metal Complexes Based on 3-Amino-1H-1,2,4-triazole-5-carboxylic Acid: From Discrete Mononuclear Complexes to Layered Materials. Molecules 2015, 20, 12341-12363. https://doi.org/10.3390/molecules200712341
Liu B, Fernandes JA, Tomé JPC, Paz FAA, Cunha-Silva L. Multidimensional Transition Metal Complexes Based on 3-Amino-1H-1,2,4-triazole-5-carboxylic Acid: From Discrete Mononuclear Complexes to Layered Materials. Molecules. 2015; 20(7):12341-12363. https://doi.org/10.3390/molecules200712341
Chicago/Turabian StyleLiu, Bing, José A. Fernandes, João P. C. Tomé, Filipe A. Almeida Paz, and Luís Cunha-Silva. 2015. "Multidimensional Transition Metal Complexes Based on 3-Amino-1H-1,2,4-triazole-5-carboxylic Acid: From Discrete Mononuclear Complexes to Layered Materials" Molecules 20, no. 7: 12341-12363. https://doi.org/10.3390/molecules200712341