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Title: Crystal structure of (E)-3-fluoro-N-((5-nitrothiophen-2-yl)methylene)aniline

Abstract

The structure of the title compound C{sub 11}H{sub 7}FN{sub 2}O{sub 2}S was characterized by single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2{sub 1}/n with Z = 12, i.e. with three molecules in asymmetric unit. The molecules are not planar: the dihedral angles between the planes of thiophene and the benzene rings are 42.3(3)°, 42.0(3)°, and 48.9(2)°. In the crystal, intermolecular C–H···F interactions link the molecules through R{sub 2}{sup 2} (14) ring motif. The crystal packing is also stabilized by π···π interactions.

Authors:
;  [1];  [2]
  1. Amasya University, Department of Physics, Faculty of Arts and Sciences (Turkey)
  2. Ondokuz Mayıs University, Department of Chemistry, Faculty of Arts and Sciences (Turkey)
Publication Date:
OSTI Identifier:
22645522
Resource Type:
Journal Article
Resource Relation:
Journal Name: Crystallography Reports; Journal Volume: 61; Journal Issue: 3; Other Information: Copyright (c) 2016 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; ANILINE; BENZENE; CRYSTAL STRUCTURE; MONOCLINIC LATTICES; MONOCRYSTALS; POLYCYCLIC SULFUR HETEROCYCLES; SPACE GROUPS; THIOPHENE; X-RAY DIFFRACTION

Citation Formats

Karataş, Şadiye, Tanak, Hasan, E-mail: hasantanak@gmail.com, and Ağar, Ayşen Alaman. Crystal structure of (E)-3-fluoro-N-((5-nitrothiophen-2-yl)methylene)aniline. United States: N. p., 2016. Web. doi:10.1134/S1063774516030147.
Karataş, Şadiye, Tanak, Hasan, E-mail: hasantanak@gmail.com, & Ağar, Ayşen Alaman. Crystal structure of (E)-3-fluoro-N-((5-nitrothiophen-2-yl)methylene)aniline. United States. doi:10.1134/S1063774516030147.
Karataş, Şadiye, Tanak, Hasan, E-mail: hasantanak@gmail.com, and Ağar, Ayşen Alaman. 2016. "Crystal structure of (E)-3-fluoro-N-((5-nitrothiophen-2-yl)methylene)aniline". United States. doi:10.1134/S1063774516030147.
@article{osti_22645522,
title = {Crystal structure of (E)-3-fluoro-N-((5-nitrothiophen-2-yl)methylene)aniline},
author = {Karataş, Şadiye and Tanak, Hasan, E-mail: hasantanak@gmail.com and Ağar, Ayşen Alaman},
abstractNote = {The structure of the title compound C{sub 11}H{sub 7}FN{sub 2}O{sub 2}S was characterized by single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2{sub 1}/n with Z = 12, i.e. with three molecules in asymmetric unit. The molecules are not planar: the dihedral angles between the planes of thiophene and the benzene rings are 42.3(3)°, 42.0(3)°, and 48.9(2)°. In the crystal, intermolecular C–H···F interactions link the molecules through R{sub 2}{sup 2} (14) ring motif. The crystal packing is also stabilized by π···π interactions.},
doi = {10.1134/S1063774516030147},
journal = {Crystallography Reports},
number = 3,
volume = 61,
place = {United States},
year = 2016,
month = 5
}
  • The synthesis and x-ray diffraction analysis (lambdaMo, 2829 reflections, anisotropic least-squares refinement to R = 0.051, localization of the H atoms) of MoO/sub 2/Cl/sub 2/ x 2L (I), where L = N(Ph) x C(Me) x CH x C(Me) x OH, have been carried out. The crystals are triclinic: a = 9.853, b = 11.216, c = 13.240 A, ..cap alpha.. = 88.52, ..beta.. = 68.16, ..gamma.. = 63.91/sup 0/, rho(mea) = 1.48 g/cm/sup 3/, Z = 2, space group P anti 1. In molecular complex I the Mo atom has octahedral coordination owing to the two cis O(oxo) atoms, themore » two O atoms of the monodentate L ligands, which are in trans positions to the O(oxo) atoms, and the two Cl atoms, which are in trans positions to one another. The mean bond lengths are: Mo-O(oxo) = 1.686, Mo-O(L) = 2.202, and Mo-Cl = 2.380 A. The Mo atom is displaced 0.159 A from the center of the octahedron toward the O(oxo)-O(oxo) edge. The Mo-O(L) bonds are elongated by approx. 0.2 A in comparison to the usual values due to the trans influence of the Mo=O(oxo) double bonds. The bonds in the O x C(Me) x C(H) x C(Me) x N fragment of ligand L are delocalized. The acid protons are localized at the N(L) atom, i.e., the molecules of L have the ketoamine form. In the molecules of L there are strong N-H...O intramolecular H bonds, which complete OHNC/sub 3/ pseudoheterocycles (on the average O...N = 2.628, H...O = 1.76 A, and the NHO angle equals 136/sup 0/). The results of the investigation of complex I have been compared with the literature data for monomeric octahedral dioxo complexes of Mo(6+) with O(L) atoms in the trans positions to the O(oxo) atoms, as well as for complexes containing 4-amino-3-penten-2-one ligands.« less
  • The structure of fluoro-apatite was investigated by the NMR technique. Two sample specimens used were the single crystals from Japan and Mexico. The resonance curves were recorded for F/sup 19/ and P/sup 31/, respectively, by the autodyne type detector. The magnetic field was about 3900 gauss, and resonance frequencies were about 15.9 Mc for F/sup 19/ and about 6.8 Mc for P/sup 31/. The second moments were 0.68 and 0.44 gauss for F/sup 19/ and P/sup 31/. The second moments were also calculated theoretically by using the x-ray data with the results of 0.54 gauss and 0.15 gauss for F/supmore » 19/ and 0.68 and 0.44 gauss for F/sup 19/ and P/sup 31/. The second moments were also calculated theoretically by using the x-ray data with the results of 0.54 gauss and 0.15 gauss for F/sup 19/ and pat. In order to explain the discrepancies between the theoretical and experimental walues of second moments, the second moment values were calculated for the models where the coordinates of phosphorus atoms were varied, and it was confirmed that the second moment value for a model is consistent with the experimental value where the coordinates for P/sup 31/ are reduced by about 20% with respect to the x-ray data. Thus the coordinates for the fluoroapatite are: F:0,0,1/4; 0,0,3/4 and P: (x,y,l/4; y,x-y,1/4; y-x,x,1/4), x = 0.333, y = 0.289. (auth)« less
  • Two new fluoro-vanadyl-hydrogenarsenate compounds templated by ethylenediamine and piperazine with formula, (C{sub 2}N{sub 2}H{sub 10}){sub 0.5}[(VO)(HAsO{sub 4})F] (1) and (C{sub 4}N{sub 2}H{sub 12}){sub 0.5}[(VO)(HAsO{sub 4})F] (2), respectively, have been synthesized by using mild hydrothermal conditions under autogenous pressure. The crystal structures have been solved from single-crystal X-ray diffraction data. The phases crystallize in the P2{sub 1}/c monoclinic space group with the unit-cell parameters a=7.8634(4) A, b=7.7658(4) A, c=10.4195(6) A, {beta}=101.524(5){sup o} for compound (1) and a=6.301(1) A, b=10.244(1) A, c=10.248(1) A and {beta}=95.225(1){sup o} for compound (2). These phases exhibit a layered inorganic framework. In both cases, the structure ismore » built from secondary building units (SBU) which are formed by [V{sub 2}O{sub 8}F{sub 2}] edge-shared dimeric vanadyl octahedra, connected by the vertices to two hydrogenarsenate tetrahedra. The repetition of this SBU unit originates sheets along the [1 0 0] direction. The ethylenediammonium and piperazinium cations are located inside the interlayer space. The limit of thermal stability for compounds (1) and (2) is, approximately, 250 and 230 deg. C, respectively. Near this temperature, both phases loose their organic cations and the fluoride anions. The diffuse reflectance spectra confirm the presence of vanadyl ions, in which the vanadium(IV) cations have a d{sup 1} electronic configuration in a slightly distorted octahedral environment. ESR spectra of both phases are isotropic with mean g-values of 1.93 and 1.96 for ethylendiamine and piperazine phases, respectively. Magnetic measurements for (1) and (2) indicate the existence of antiferromagnetic exchange couplings. - Graphical abstract: Polyhedral view of the layered crystal structure of (C{sub 2}H{sub 10}N{sub 2}){sub 0.5} [(VO)(HAsO{sub 4})F].« less
  • The /sup 31/P NMR spectra of methylene and fluoro analogues of adenine nucleotides have been studied as a function of pH and Mg/sup 2 +/ concentration. As expected, the spectra of the fluoro analogues are not a function of pH. Mg/sup 2 +/ titrations show that both fluoro analogues bind the metal ion less strongly than ATP or ADP, respectively. For the analogues AMPPCP (..beta..,..gamma..) and AMPCP (..cap alpha..,..beta..), a pK/sub a/ near 8.1 was deduced for the titration of the terminal phosphoryl group; in the presence of Mg/sup 2 +/ this value is lowered to about 6.3. The othermore » ATP analogue, AMPCPP (..cap alpha..,..beta..), has a titration behavior virtually identical with that of ATP. Therefore, at physiological pH all adenine nucleotides will be fully deprotonated in the presence of Mg/sup 2 +/ ions. A comparison of the magnitudes and directions of the chemical shift changes observed due to protonation leads to the conclusion that these are caused by changes in the structure of the polyphosphate chain. Mutual titrations indicate that both methylene ATP analogues can bind one Mg/sup 2 +/ tightly and a second ion more weakly. The methylene analogue of ADP binds only one Mg/sup 2 +/. These data show that the methylene analogues compare favorably with ATP and ADP with respect to metal binding properties. A comparison of the results with those reported for imido- and thioadenine analogues suggests that the /sup 31/P NMR spectra for metal complexed nucleotides fee in solution are probably the fact-exchange average of all metal-coordination structures possible. This raises questions about the validity of direct comparisons of these spectra to those observed for enzyme-bound nucleotides. (JMT)« less