Crystal structure and Hirshfeld surface analysis of <i>N</i>-(5-iodo-4-phenylthiazol-2-yl)acetamide

Herrera-España, Angel D.; Aguilera-González, Jesús; Hernández‐Ortega, Simón; Cáceres-Castillo, David

doi:10.1107/s2056989019004791

Cited by 4 publications

(3 citation statements)

References 19 publications

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“…The strongest, intermediate, and weak interactions are indicated by red, white, and blue color, respectively. Surfaces are constructed by an assumption that is the electron distribution around the atom is formulated as a summation of spherical atom electron densities. − In Figure [AMPBS(a)], the ring nitrogen of the 2-amino-6-methylpyrimidin-4-ol moiety that is the nearest to the methyl group, the amino group, and methyl group of 2-amino-6-methylpyrimidin-4-ol moiety and one of the oxygen atom of sulfonyl group are involved in strong interaction as shown in Figure [AMPBS(a)]. Amino groups, ring nitrogens, ring CH, and one of the oxygen atoms of the sulfonyl group are involved in strong interactions in compound DAPBS, as shown in Figure [DAPBS (a)].…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis, SC-XRD, and Theoretical Studies of O-Benzenesulfonylated Pyrimidines: Role of Noncovalent Interaction Influence in Their Supramolecular Network

et al. 2020

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Crystalline organic compounds, 2-amino-6-methylpyrimidin-4-yl benzenesulfonate (AMPBS) and 2,6-diaminopyrimidin-4-yl benzenesulfonate (DAPBS), were prepared via O-benzenesulfonylation of 2-amino-6-methylpyrimidin-4-ol 1 and 2,6-diaminopyrimidin-4-ol 2, respectively. The structural interpretations were achieved unambiguously by single-crystal X-ray diffraction (SC-XRD) analysis. The Hirshfeld surface study showed that C−Hhydrogen bond interactions are the key contributors to the intermolecular stabilization in the crystal. Density functional theory (DFT) studies were used to obtain a better understanding of natural bond orbitals (NBOs) and nonlinear optical (NLO) analysis for AMPBS and DAPBS at the B3LYP/6-311G(d,p) level. The time-dependent density functional theory (TD-DFT)/CAM-B3LYP/6-311G(d,p) level was employed for frontier molecular orbital analysis of both compounds. DFT-based vibrations for C− H, CN, N−H, and stretching for C−C were found to be in good agreement with the experimental data. Overall, the theoretical findings were acquired in correspondence to the SC-XRD-based parameters. Intracharge transfer occurred in AMPBS and DAPBS compounds, which was evaluated through FMO activity. Global reactivity indices had been acquired utilizing energies of HOMO−LUMO orbitals. Overall, the theoretical findings related to AMPBS and DAPBS consist of promising correspondence to experimental findings. The theoretical-based study also exhibited that both AMPBS and DAPBS compounds contain promising NLO features.

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Section: Resultsmentioning

confidence: 99%

Efficient Synthesis, SC-XRD, and Theoretical Studies of O-Benzenesulfonylated Pyrimidines: Role of Noncovalent Interaction Influence in Their Supramolecular Network

et al. 2020

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“…In both A and B , the white color of HS near the pyrimidine and benzene rings indicated the presence of parallel offset stacking interactions. In Figure S1c,d, HS was mapped over d e in the ranges 0.849–2.761 and 0.859–2.769 au for A and B , respectively, with d e representing the closest space of an atom contained by the HS to the atom within its surrounding. , The smallest, intermediate, and long distances were denoted by red, green, and blue colors, respectively. In Figure S1e,f, HS was mapped throughout the shape index in the range −1 to 1 au for both molecules.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Diaminopyrimidine Sulfonate Derivatives and Exploration of Their Structural and Quantum Chemical Insights via SC-XRD and the DFT Approach

et al. 2021

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Two heterocyclic compounds named 2,6-diaminopyrimidin-4-ylnaphthalene-2-sulfonate ( A ) and 2,6-diaminopyrimidin-4-yl4-methylbenzene sulfonate ( B ) were synthesized. The structures of heterocyclic molecules were established by the X-ray crystallographic technique, which showed several noncovalent interactions as N···H···N, N···H···O, and C–H···O bonding and parallel offset stacking interaction. Hydrogen-bonding interactions were further explored by the Hirshfeld surface (HS) analysis. Nonlinear optical (NLO) and natural bond orbital (NBO) properties were calculated utilizing the B3LYP/6-311G(d,p) level. Frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) were calculated utilizing the time-dependent density functional theory (TD-DFT) at the same level. The NBO analysis showed that the molecular stabilities of compounds A and B were attributed to their large stabilization energy values. The second hyperpolarizability (γ tot ) values for A and B were obtained as 3.7 × 10 4 and 2.7 × 10 4 au, respectively. The experimental X-ray crystallographic and theoretical structural parameters of A and B were found to be in close correspondence. Both the molecules reveal substantial NLO responses that can be significant for their utilization in advanced applications.

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“…Each point of the Hirshfeld surface contained two kinds of critical distances viz de and di, these were the distances from that point to the adjacent nucleus, outward and inward to the surface of molecule respectively. 42,43 Hirshfeld surface analysis for 1, 2 and 3 was done to estimate the strength of intermolecular interactions. The Hirshfeld surface structure for compounds 1, 2 and 3 are arranged in Fig.…”

Section: Hirshfeld Analysismentioning

confidence: 99%

Exploration of CH⋯F & CF⋯H mediated supramolecular arrangements into fluorinated terphenyls and theoretical prediction of their third-order nonlinear optical response

et al. 2021

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Crystal structure and Hirshfeld surface analysis of N-(5-iodo-4-phenylthiazol-2-yl)acetamide

Cited by 4 publications

References 19 publications

Efficient Synthesis, SC-XRD, and Theoretical Studies of O-Benzenesulfonylated Pyrimidines: Role of Noncovalent Interaction Influence in Their Supramolecular Network

Efficient Synthesis, SC-XRD, and Theoretical Studies of O-Benzenesulfonylated Pyrimidines: Role of Noncovalent Interaction Influence in Their Supramolecular Network

Synthesis of Diaminopyrimidine Sulfonate Derivatives and Exploration of Their Structural and Quantum Chemical Insights via SC-XRD and the DFT Approach

Exploration of CH⋯F & CF⋯H mediated supramolecular arrangements into fluorinated terphenyls and theoretical prediction of their third-order nonlinear optical response

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