<i>S</i>-Benzylthiouronium 3-nitrobenzenesulfonate

Fun, Hoong‐Kun; Jebas, Samuel Robinson; Razak, Ibrahim Abdul; D'Silva, E. Deepak; Patil, P. S.; Dharmaprakash, S. M.

doi:10.1107/s1600536808016115

Cited by 9 publications

(13 citation statements)

References 10 publications

(10 reference statements)

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“…1 and Table 1). Bond lengths and angles in molecules A and B are slightly different but all are in normal ranges (Allen et al, 1987) and comparable to those in a related structure (Fun et al, 2008).…”

Section: S1 Commentsupporting

confidence: 53%

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3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one

et al. 2008

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.005 Å; disorder in main residue; R factor = 0.063; wR factor = 0.172; data-to-parameter ratio = 18.8.The title chalcone derivative, C 13 H 8 ClFOS, crystallized as an inversion twin with two independent molecules in the asymmetric unit. The thiophene rings in both molecules are disordered over two sites: the ratios of occupancies for the major and minor components in the two molecules are 0.820 (2):0.180 (2) and 0.853 (2):0.147 (2). The dihedral angles between the major and minor components of the thiophene and benzene rings are 1.13 (18) and 2.2 (6) , respectively, in one molecule, with corresponding values 6.09 (17) and 1.3 (6) in the other. Weak intramolecular C-HÁ Á ÁO and C-HÁ Á ÁF interactions involving the prop-2-en-1-one group generate an S(5)S(5) ring motif, whereas a weak intramolecular C-HÁ Á ÁCl contact generates an S(6) ring motif. In the crystal structure, molecules of both the major and minor components are linked into infinite one-dimensional chains along the b axis. The crystal structure is stabilized by weak C-HÁ Á ÁO, C-HÁ Á ÁF, C-HÁ Á ÁCl and C-HÁ Á Á interactions. Related literature

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Section: S1 Commentsupporting

confidence: 53%

“…For bond-length data, see: Allen et al (1987). For related structures, see, for example: Fun et al (2008); Patil et al (2007b,c). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al (1999); Chopra et al (2007).…”

Section: Related Literaturementioning

confidence: 99%

3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one

et al. 2008

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“…The pyrimidine rings have a perpendicular separation of 3.442 Å and a centroid-centroid (Cg1Á Á ÁCg2) distance of 3.9245 (12) Å (Cg1 is the centroid of the N1A/N3A/C2A-C6A ring and Cg2 is the centroid of the N1B/N3B/C2B-C6B ring). Intramolecular N-HÁ Á ÁCl and C-HÁ Á ÁCl hydrogen bonds are also observed for A and B (Table 2) (Wang et al, 2012;Fun et al, 2008). Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) and SHELXLE (Hübschle et al, 2011); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).…”

Section: Figurementioning

confidence: 85%

Supramolecular hydrogen-bonding patterns in the organic–inorganic hybrid compound bis(4-amino-5-chloro-2,6-dimethylpyrimidinium) tetrathiocyanatozinc(II)–4-amino-5-chloro-2,6-dimethylpyrimidine–water (1/2/2)

2016

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Zinc thiocyanate complexes have been found to be biologically active compounds. Zinc is also an essential element for the normal function of most organisms and is the main constituent in a number of metalloenzyme proteins. Pyrimidine and aminopyrimidine derivatives are biologically very important as they are components of nucleic acids. Thiocyanate ions can bridge metal ions by employing both their N and S atoms for coordination. They can play an important role in assembling different coordination structures and yield an interesting variety of one-, two- and three-dimensional polymeric metal-thiocyanate supramolecular frameworks. The structure of a new zinc thiocyanate-aminopyrimidine organic-inorganic compound, (C6H9ClN3)2[Zn(NCS)4]·2C6H8ClN3·2H2O, is reported. The asymmetric unit consist of half a tetrathiocyanatozinc(II) dianion, an uncoordinated 4-amino-5-chloro-2,6-dimethylpyrimidinium cation, a 4-amino-5-chloro-2,6-dimethylpyrimidine molecule and a water molecule. The Zn(II) atom adopts a distorted tetrahedral coordination geometry and is coordinated by four N atoms from the thiocyanate anions. The Zn(II) atom is located on a special position (twofold axis of symmetry). The pyrimidinium cation and the pyrimidine molecule are not coordinated to the Zn(II) atom, but are hydrogen bonded to the uncoordinated water molecules and the metal-coordinated thiocyanate ligands. The pyrimidine molecules and pyrimidinium cations also form base-pair-like structures with an R2(2)(8) ring motif via N-H...N hydrogen bonds. The crystal structure is further stabilized by intermolecular N-H...O, O-H...S, N-H...S and O-H...N hydrogen bonds, by intramolecular N-H...Cl and C-H...Cl hydrogen bonds, and also by π-π stacking interactions.

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“…For general background to the biological activity of similar compounds, see: Dimmock et al (1999); Lin et al (2002); Nakamura et al (2002); Nowakowska (2007); Opletalova & Sedivy (1999). For related structures, see: Butcher et al (2006Butcher et al ( , 2007; Chopra et al (2007); Fun et al (2008); Jasinski et al (2009); Patil et al (2007); Qiu et al (2006); Teh et al (2007). For density functional theory (DFT), see: Becke (1988Becke ( , 1993; Hehre et al (1986); Lee et al (1988); Schmidt & Polik (2007).…”

Section: Related Literaturementioning

confidence: 99%

A second polymorph of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

et al. 2009

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The crystal structure of the title compound, C18H17FO4, reported here is a polymorph of the structure first reported by Patil et al. [Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A (2007), 461, 123–130]. It is a chalcone analog and consists of substituted phenyl rings bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between the mean planes of the aromatic rings within the 4-fluorophenyl and trimethoxyphenyl groups is 28.7 (1)° compared to 20.8 (6)° in the published structure. The angles between the mean plane of the prop-2-ene-1-one group and the mean plane of aromatic rings within the 4-fluorophenyl and trimethoxyphenyl groups are 30.3 (4) and 7.4 (7)°, respectively, in contast to 10.7 (3) and 12.36° for the polymorph. While the two 3-methoxy groups are in the plane of the trimethoxy-substituted ring, the 4-methoxy group is in a synclinical [−sc = −78.1 (2)°] or anticlinical [+ac = 104.0 (4)°] position, compared to a +sc [53.0 (4)°] or −ac [−132.4 (7)°] position. While no classical hydrogen bonds are present, weak intermolecular C—H⋯π-ring interactions are observed which contribute to the stability of the crystal packing. The two polymorphs crystallize in the same space group, P21/c, but have different cell parameters for the a, b and c axes and the β angle. A comparison of the molecular geometries of both polymorphs to a geometry optimized density functional theory (DFT) calculation at the B3-LYP/6–311+G(d,p) level for each structure provides additional support to these observations.

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S-Benzylthiouronium 3-nitrobenzenesulfonate

Cited by 9 publications

References 10 publications

3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one

3-(2-Chloro-6-fluorophenyl)-1-(2-thienyl)prop-2-en-1-one

Supramolecular hydrogen-bonding patterns in the organic–inorganic hybrid compound bis(4-amino-5-chloro-2,6-dimethylpyrimidinium) tetrathiocyanatozinc(II)–4-amino-5-chloro-2,6-dimethylpyrimidine–water (1/2/2)

A second polymorph of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

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