TY  - JOUR
AU  - Francuski, Bojana M.
AU  - Novaković, Slađana B.
AU  - Francuski, Đorđe D.
AU  - Bogdanović, Goran A.
PY  - 2017
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1601
AB  - Charge density distribution in 2-pyridineformamide N(4)-methylthiosemicarbazone (TSC4) has been determined using high-resolution X-ray diffraction data (100 K) and Hansen-Coppens multipole formalism. The results are interpreted in terms of Baders quantum theory of atoms in molecules (QTAIM), electrostatic potential analysis, and theoretical calculations (CRYSTAL09). The study highlights the molecular diSsimilarity at the electronic level. The N-H center dot center dot center dot S interactions have a dominant role in Stabilization of the TSC4 crystal Structure. As each of the four S acceptors simultaneously engages in several interactions, the focus of study is on the lone pairs electron density of these acceptors which is particularly able to adjust to the various spatial distributions of the interacting donor groups. The main structural feature of TSC4 is the formation of specific N-H center dot center dot center dot S bonded dimers between two pairs of independent molecules. These dimers are the main building block in the orkstal structure, and with the two additional N-H center dot center dot center dot S contacts they represent a significant enhancement of a typical R-2(2)(8) dirtier synthon which dominates among the thioureido-based crystal structures. Two TSC4 dimers are structurally very similar and exhibit considerable cohesive energy (-20.8 and 21.4 kcal/mol). This: type of dimer is the only structural motif that is common for S acceptors of all four independent molecules.
T2  - Crystal Growth and Design
T1  - Charge Density Analysis of 2-Pyridineformamide N(4)-Methylthiosemicarbazone (Z =4): Role of an Enhanced N-H center dot center dot center dot S Thioureido Dimer
VL  - 17
IS  - 6
SP  - 2993
EP  - 3004
DO  - 10.1021/acs.cgd.6b01620
ER  - 

@article{
author = "Francuski, Bojana M. and Novaković, Slađana B. and Francuski, Đorđe D. and Bogdanović, Goran A.",
year = "2017",
abstract = "Charge density distribution in 2-pyridineformamide N(4)-methylthiosemicarbazone (TSC4) has been determined using high-resolution X-ray diffraction data (100 K) and Hansen-Coppens multipole formalism. The results are interpreted in terms of Baders quantum theory of atoms in molecules (QTAIM), electrostatic potential analysis, and theoretical calculations (CRYSTAL09). The study highlights the molecular diSsimilarity at the electronic level. The N-H center dot center dot center dot S interactions have a dominant role in Stabilization of the TSC4 crystal Structure. As each of the four S acceptors simultaneously engages in several interactions, the focus of study is on the lone pairs electron density of these acceptors which is particularly able to adjust to the various spatial distributions of the interacting donor groups. The main structural feature of TSC4 is the formation of specific N-H center dot center dot center dot S bonded dimers between two pairs of independent molecules. These dimers are the main building block in the orkstal structure, and with the two additional N-H center dot center dot center dot S contacts they represent a significant enhancement of a typical R-2(2)(8) dirtier synthon which dominates among the thioureido-based crystal structures. Two TSC4 dimers are structurally very similar and exhibit considerable cohesive energy (-20.8 and 21.4 kcal/mol). This: type of dimer is the only structural motif that is common for S acceptors of all four independent molecules.",
journal = "Crystal Growth and Design",
title = "Charge Density Analysis of 2-Pyridineformamide N(4)-Methylthiosemicarbazone (Z =4): Role of an Enhanced N-H center dot center dot center dot S Thioureido Dimer",
volume = "17",
number = "6",
pages = "2993-3004",
doi = "10.1021/acs.cgd.6b01620"
}

Francuski, B. M., Novaković, S. B., Francuski, Đ. D.,& Bogdanović, G. A.. (2017). Charge Density Analysis of 2-Pyridineformamide N(4)-Methylthiosemicarbazone (Z =4): Role of an Enhanced N-H center dot center dot center dot S Thioureido Dimer. in Crystal Growth and Design, 17(6), 2993-3004.
https://doi.org/10.1021/acs.cgd.6b01620

Francuski BM, Novaković SB, Francuski ĐD, Bogdanović GA. Charge Density Analysis of 2-Pyridineformamide N(4)-Methylthiosemicarbazone (Z =4): Role of an Enhanced N-H center dot center dot center dot S Thioureido Dimer. in Crystal Growth and Design. 2017;17(6):2993-3004.
doi:10.1021/acs.cgd.6b01620 .

Francuski, Bojana M., Novaković, Slađana B., Francuski, Đorđe D., Bogdanović, Goran A., "Charge Density Analysis of 2-Pyridineformamide N(4)-Methylthiosemicarbazone (Z =4): Role of an Enhanced N-H center dot center dot center dot S Thioureido Dimer" in Crystal Growth and Design, 17, no. 6 (2017):2993-3004,
https://doi.org/10.1021/acs.cgd.6b01620 . .

TY  - JOUR
AU  - Francuski, Bojana M.
AU  - Novaković, Slađana B.
AU  - Ostojić, Bojana D.
AU  - Francuski, Đorđe D.
AU  - Bogdanović, Goran A.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/671
AB  - Theoretical charge density analysis of the thioureido based compound 4-methyl-3-thiosemicarbazide (MeTSC) is used in this study with the aim to provide additional insight into electronic features of the thioureido sulfur acceptor and the corresponding D-H...S hydrogen bonding (D=N, C). The present work is motivated by our earlier experimental charge density study on the same compound that pointed out to a great flexibility of the thioureido S acceptor and its ability to adjust the lone pair electron density to the donor groups in simultaneous hydrogen bonding. Through the additional theoretical approach we were able to single out different fragments of MeTSC crystal and to carefully follow the changes in electron density properties of the S acceptors belonging to: isolated MeTSC monomers (i.e. two crystallographically independent molecules), eight D-H...S bonded dimers and MeTSC molecules placed in full crystal environment, where each S atom engages in four hydrogen bonds. Deformation density of the sulfurs lone electron pair, topological properties of D-H...S interactions and electrostatic potential are here examined in order to comprehend the mutual influence and potential cooperative effects of the four simultaneously formed interactions to each of the S acceptors. The hydrogen bonding involving thioureido S acceptor is also investigated in terms of the energetic properties of the eight real MeTSC dimers existing in the crystal structure, and additional systems MeTSC/MeOH and acetone/MeOH. The latter systems are designed with the purpose of direct comparison and ranking of interactions involving thioureido S to those involving more conventional, carbonyl O acceptor. Energetic features were thoroughly studied through electrostatic interactions energies (XD2006), cohesive energies (CRYSTAL09) and ab initio approach employing the coupled-cluster single S and doubles augmented by a perturbational correction for connected triple excitations (CCSD(T)) method. (C) 2015 Elsevier B.V. All rights reserved.
T2  - Computational and Theoretical Chemistry
T1  - Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study
VL  - 1067
SP  - 93
EP  - 102
DO  - 10.1016/j.comptc.2015.05.024
ER  - 

@article{
author = "Francuski, Bojana M. and Novaković, Slađana B. and Ostojić, Bojana D. and Francuski, Đorđe D. and Bogdanović, Goran A.",
year = "2015",
abstract = "Theoretical charge density analysis of the thioureido based compound 4-methyl-3-thiosemicarbazide (MeTSC) is used in this study with the aim to provide additional insight into electronic features of the thioureido sulfur acceptor and the corresponding D-H...S hydrogen bonding (D=N, C). The present work is motivated by our earlier experimental charge density study on the same compound that pointed out to a great flexibility of the thioureido S acceptor and its ability to adjust the lone pair electron density to the donor groups in simultaneous hydrogen bonding. Through the additional theoretical approach we were able to single out different fragments of MeTSC crystal and to carefully follow the changes in electron density properties of the S acceptors belonging to: isolated MeTSC monomers (i.e. two crystallographically independent molecules), eight D-H...S bonded dimers and MeTSC molecules placed in full crystal environment, where each S atom engages in four hydrogen bonds. Deformation density of the sulfurs lone electron pair, topological properties of D-H...S interactions and electrostatic potential are here examined in order to comprehend the mutual influence and potential cooperative effects of the four simultaneously formed interactions to each of the S acceptors. The hydrogen bonding involving thioureido S acceptor is also investigated in terms of the energetic properties of the eight real MeTSC dimers existing in the crystal structure, and additional systems MeTSC/MeOH and acetone/MeOH. The latter systems are designed with the purpose of direct comparison and ranking of interactions involving thioureido S to those involving more conventional, carbonyl O acceptor. Energetic features were thoroughly studied through electrostatic interactions energies (XD2006), cohesive energies (CRYSTAL09) and ab initio approach employing the coupled-cluster single S and doubles augmented by a perturbational correction for connected triple excitations (CCSD(T)) method. (C) 2015 Elsevier B.V. All rights reserved.",
journal = "Computational and Theoretical Chemistry",
title = "Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study",
volume = "1067",
pages = "93-102",
doi = "10.1016/j.comptc.2015.05.024"
}

Francuski, B. M., Novaković, S. B., Ostojić, B. D., Francuski, Đ. D.,& Bogdanović, G. A.. (2015). Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study. in Computational and Theoretical Chemistry, 1067, 93-102.
https://doi.org/10.1016/j.comptc.2015.05.024

Francuski BM, Novaković SB, Ostojić BD, Francuski ĐD, Bogdanović GA. Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study. in Computational and Theoretical Chemistry. 2015;1067:93-102.
doi:10.1016/j.comptc.2015.05.024 .

Francuski, Bojana M., Novaković, Slađana B., Ostojić, Bojana D., Francuski, Đorđe D., Bogdanović, Goran A., "Electronic features and hydrogen bonding capacity of the sulfur acceptor in thioureido-based compounds. Part 2. Further insight by theoretical charge density study" in Computational and Theoretical Chemistry, 1067 (2015):93-102,
https://doi.org/10.1016/j.comptc.2015.05.024 . .

TY  - JOUR
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Heering, Christian
AU  - Makhloufi, Gamall
AU  - Francuski, Đorđe D.
AU  - Janiak, Christoph
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/452
AB  - The electron-density distribution in a prototypical porous coordination polymer ZIF-8 has been obtained in an approach combining high-resolution X-ray diffraction data and Invariom refinement. In addition, the periodic quantum-chemical calculation has been used to describe the theoretical density features of ZIF-8 in the same geometry (m1) and also in a high-pressure form of ZIF-8 (m2) characterized by conformational change with respect to the methylimidazolate linker. A thorough comparison of the electronic and electrostatic properties in two limiting structural forms of ZIF-8 proposes additional aspects on diffusion and adsorption processes occurring within the framework. The dimensions of the four-membered (FM) and six-membered (SM) apertures of the beta cage are reliably determined from the total electron-density distribution. The analysis shows that FM in m2 becomes competitive in size to the SM aperture and should be considered for the diffusion of small molecules and cations. Baders topological analysis (quantum theory of atoms in molecules) shows similar properties of both ZIF-8 forms. On the other hand, analysis of their electrostatic properties reveals tremendous differences. The study suggests exceptional electrostatic flexibility of the ZIF-8 framework, where small conformational changes lead to a significantly different electrostatic potential (EP) distribution, a feature that could be important for the function and dynamics of the ZIF-8 framework. The cavity surface in m1 contains 38 distinct regions with moderately positive, negative, or neutral EP and weakly positive EP in the cavity volume. In contrast to m1, the m2 form displays only two regions of different EP, with the positive one taking the whole cavity surface and the strong negative one localized entirely in the FM apertures. The EP in the cavity volume is also more positive than that in m1. A pronounced influence of the linker reorientation on the EP of the ZIF-8 forms is related to the high symmetry of the system and to an amplification of the electrostatic properties by cooperative effects of the proximally arranged structural fragments.
T2  - Inorganic Chemistry
T1  - Charge-Density Distribution and Electrostatic Flexibility of ZIF-8 Based on High-Resolution X-ray Diffraction Data and Periodic Calculations
VL  - 54
IS  - 6
SP  - 2660
EP  - 2670
DO  - 10.1021/ic5028256
ER  - 

@article{
author = "Novaković, Slađana B. and Bogdanović, Goran A. and Heering, Christian and Makhloufi, Gamall and Francuski, Đorđe D. and Janiak, Christoph",
year = "2015",
abstract = "The electron-density distribution in a prototypical porous coordination polymer ZIF-8 has been obtained in an approach combining high-resolution X-ray diffraction data and Invariom refinement. In addition, the periodic quantum-chemical calculation has been used to describe the theoretical density features of ZIF-8 in the same geometry (m1) and also in a high-pressure form of ZIF-8 (m2) characterized by conformational change with respect to the methylimidazolate linker. A thorough comparison of the electronic and electrostatic properties in two limiting structural forms of ZIF-8 proposes additional aspects on diffusion and adsorption processes occurring within the framework. The dimensions of the four-membered (FM) and six-membered (SM) apertures of the beta cage are reliably determined from the total electron-density distribution. The analysis shows that FM in m2 becomes competitive in size to the SM aperture and should be considered for the diffusion of small molecules and cations. Baders topological analysis (quantum theory of atoms in molecules) shows similar properties of both ZIF-8 forms. On the other hand, analysis of their electrostatic properties reveals tremendous differences. The study suggests exceptional electrostatic flexibility of the ZIF-8 framework, where small conformational changes lead to a significantly different electrostatic potential (EP) distribution, a feature that could be important for the function and dynamics of the ZIF-8 framework. The cavity surface in m1 contains 38 distinct regions with moderately positive, negative, or neutral EP and weakly positive EP in the cavity volume. In contrast to m1, the m2 form displays only two regions of different EP, with the positive one taking the whole cavity surface and the strong negative one localized entirely in the FM apertures. The EP in the cavity volume is also more positive than that in m1. A pronounced influence of the linker reorientation on the EP of the ZIF-8 forms is related to the high symmetry of the system and to an amplification of the electrostatic properties by cooperative effects of the proximally arranged structural fragments.",
journal = "Inorganic Chemistry",
title = "Charge-Density Distribution and Electrostatic Flexibility of ZIF-8 Based on High-Resolution X-ray Diffraction Data and Periodic Calculations",
volume = "54",
number = "6",
pages = "2660-2670",
doi = "10.1021/ic5028256"
}

Novaković, S. B., Bogdanović, G. A., Heering, C., Makhloufi, G., Francuski, Đ. D.,& Janiak, C.. (2015). Charge-Density Distribution and Electrostatic Flexibility of ZIF-8 Based on High-Resolution X-ray Diffraction Data and Periodic Calculations. in Inorganic Chemistry, 54(6), 2660-2670.
https://doi.org/10.1021/ic5028256

Novaković SB, Bogdanović GA, Heering C, Makhloufi G, Francuski ĐD, Janiak C. Charge-Density Distribution and Electrostatic Flexibility of ZIF-8 Based on High-Resolution X-ray Diffraction Data and Periodic Calculations. in Inorganic Chemistry. 2015;54(6):2660-2670.
doi:10.1021/ic5028256 .

Novaković, Slađana B., Bogdanović, Goran A., Heering, Christian, Makhloufi, Gamall, Francuski, Đorđe D., Janiak, Christoph, "Charge-Density Distribution and Electrostatic Flexibility of ZIF-8 Based on High-Resolution X-ray Diffraction Data and Periodic Calculations" in Inorganic Chemistry, 54, no. 6 (2015):2660-2670,
https://doi.org/10.1021/ic5028256 . .

TY  - JOUR
AU  - Dobričić, Vladimir
AU  - Francuski, Bojana M.
AU  - Jaćević, Vesna
AU  - Rodić, Marko V.
AU  - Vladimirov, Sote
AU  - Čudina, Olivera
AU  - Francuski, Đorđe D.
PY  - 2015
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/866
AB  - The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and its crystal structure characterized by the X-ray diffraction method. The crystal system is orthorhombic with space group P2(1)2(1)2(1) and cell constants a = 8.2969(3) angstrom, b = 18.9358(8) angstrom, c = 20.0904(6) angstrom, V = 3156.4(2) angstrom(3) and Z = 4. Ring A of the steroid nucleus and phenyl ring in the 17 beta-side chain are almost planar. Rings B and C have a slightly distorted chair conformation, whereas ring D has an envelope conformation. The packing of DF is characterized by a network of intermolecular hydrogen bonds involving the O4 atom from one side of the steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond acceptors. Apart from the intermolecular hydrogen bonds in the crystal packing, there are also numerous intramolecular hydrogen bonds of the N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H center dot center dot center dot F type. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone.
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid
VL  - 80
IS  - 12
SP  - 1481
EP  - 1488
DO  - 10.2298/JSC150505067D
ER  - 

@article{
author = "Dobričić, Vladimir and Francuski, Bojana M. and Jaćević, Vesna and Rodić, Marko V. and Vladimirov, Sote and Čudina, Olivera and Francuski, Đorđe D.",
year = "2015",
abstract = "The L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid (DF) was synthesized and its crystal structure characterized by the X-ray diffraction method. The crystal system is orthorhombic with space group P2(1)2(1)2(1) and cell constants a = 8.2969(3) angstrom, b = 18.9358(8) angstrom, c = 20.0904(6) angstrom, V = 3156.4(2) angstrom(3) and Z = 4. Ring A of the steroid nucleus and phenyl ring in the 17 beta-side chain are almost planar. Rings B and C have a slightly distorted chair conformation, whereas ring D has an envelope conformation. The packing of DF is characterized by a network of intermolecular hydrogen bonds involving the O4 atom from one side of the steroid nucleus and O1 and F1 atoms from the other side as hydrogen bond acceptors. Apart from the intermolecular hydrogen bonds in the crystal packing, there are also numerous intramolecular hydrogen bonds of the N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H center dot center dot center dot F type. The local anti-inflammatory activity of DF was evaluated using the croton oil-induced ear oedema test. This derivative achieved maximal inhibition of ear oedema at significantly lower concentration in comparison with dexamethasone.",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid",
volume = "80",
number = "12",
pages = "1481-1488",
doi = "10.2298/JSC150505067D"
}

Dobričić, V., Francuski, B. M., Jaćević, V., Rodić, M. V., Vladimirov, S., Čudina, O.,& Francuski, Đ. D.. (2015). Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid. in Journal of the Serbian Chemical Society, 80(12), 1481-1488.
https://doi.org/10.2298/JSC150505067D

Dobričić V, Francuski BM, Jaćević V, Rodić MV, Vladimirov S, Čudina O, Francuski ĐD. Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid. in Journal of the Serbian Chemical Society. 2015;80(12):1481-1488.
doi:10.2298/JSC150505067D .

Dobričić, Vladimir, Francuski, Bojana M., Jaćević, Vesna, Rodić, Marko V., Vladimirov, Sote, Čudina, Olivera, Francuski, Đorđe D., "Synthesis, crystal structure and local anti-inflammatory activity of the L-phenylalanine methyl ester derivative of dexamethasone-derived cortienic acid" in Journal of the Serbian Chemical Society, 80, no. 12 (2015):1481-1488,
https://doi.org/10.2298/JSC150505067D . .

TY  - JOUR
AU  - Jaćimović, Željko K.
AU  - Leovac, Vukadin M.
AU  - Francuski, Đorđe D.
AU  - Drašković, Bojana M.
AU  - Bogdanović, Goran A.
PY  - 2009
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/3882
AB  - C6H10Cl2CuN4, monoclinic, P2(1)/n (no. 14), a = 7.316(2) angstrom b = 16.002(2) angstrom, c = 9.202(6) angstrom, beta = 113.15 (2)degrees, V = 990.6 angstrom(3), Z = 4, R-gt(F) = 0.054, wR(ref)(F-2) = 0.125, T = 293 K.
T2  - Zeitschrift fur Kristallographie = New Crystal Structures
T1  - Crystal structure of dicholoro-(3,5-dimethyl-1H-pyrazole-1-carboxamidine-N, N′)copper(II), Cu(C6H10N4)Cl2
VL  - 224
IS  - 4
SP  - 569
EP  - 570
DO  - 10.1524/ncrs.2009.0249
ER  - 

@article{
author = "Jaćimović, Željko K. and Leovac, Vukadin M. and Francuski, Đorđe D. and Drašković, Bojana M. and Bogdanović, Goran A.",
year = "2009",
abstract = "C6H10Cl2CuN4, monoclinic, P2(1)/n (no. 14), a = 7.316(2) angstrom b = 16.002(2) angstrom, c = 9.202(6) angstrom, beta = 113.15 (2)degrees, V = 990.6 angstrom(3), Z = 4, R-gt(F) = 0.054, wR(ref)(F-2) = 0.125, T = 293 K.",
journal = "Zeitschrift fur Kristallographie = New Crystal Structures",
title = "Crystal structure of dicholoro-(3,5-dimethyl-1H-pyrazole-1-carboxamidine-N, N′)copper(II), Cu(C6H10N4)Cl2",
volume = "224",
number = "4",
pages = "569-570",
doi = "10.1524/ncrs.2009.0249"
}

Jaćimović, Ž. K., Leovac, V. M., Francuski, Đ. D., Drašković, B. M.,& Bogdanović, G. A.. (2009). Crystal structure of dicholoro-(3,5-dimethyl-1H-pyrazole-1-carboxamidine-N, N′)copper(II), Cu(C6H10N4)Cl2. in Zeitschrift fur Kristallographie = New Crystal Structures, 224(4), 569-570.
https://doi.org/10.1524/ncrs.2009.0249

Jaćimović ŽK, Leovac VM, Francuski ĐD, Drašković BM, Bogdanović GA. Crystal structure of dicholoro-(3,5-dimethyl-1H-pyrazole-1-carboxamidine-N, N′)copper(II), Cu(C6H10N4)Cl2. in Zeitschrift fur Kristallographie = New Crystal Structures. 2009;224(4):569-570.
doi:10.1524/ncrs.2009.0249 .

Jaćimović, Željko K., Leovac, Vukadin M., Francuski, Đorđe D., Drašković, Bojana M., Bogdanović, Goran A., "Crystal structure of dicholoro-(3,5-dimethyl-1H-pyrazole-1-carboxamidine-N, N′)copper(II), Cu(C6H10N4)Cl2" in Zeitschrift fur Kristallographie = New Crystal Structures, 224, no. 4 (2009):569-570,
https://doi.org/10.1524/ncrs.2009.0249 . .