2H-Thiochromene-2-thione
01 Nov 2004-Acta Crystallographica Section E-structure Reports Online (International Union of Crystallography)-Vol. 60, Iss: 11
TL;DR: The crystal structure of 2H-1-benzothiopyran-2-thione, also known as dithiocoumarin, has been determined as mentioned in this paper.
Abstract: The crystal structure of the title compound (systematic name: 2H-1-benzothiopyran-2-thione), $C_9H_6S_2$, also known as dithiocoumarin, has been determined. The molecule is essentially planar and the structure is stabilized via $S\cdot\cdot\cdot S $ and $C- H\cdot\cdot\cdot\pi$ interactions.
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TL;DR: Nishio et al. as discussed by the authors survey recent results relevant to the CH/π hydrogen bond: crystal conformation, packing and host/guest chemistry, and summarize the results obtained by crystallographic database (CSD and PDB) analyses.
Abstract: This treatise is an update to a preceding highlight (CH/π hydrogen bonds in crystals) published in this journal 5 years ago (M. Nishio, CrystEngComm, 2004, 6, 130–156). After the introductory part (sections 1 and 2), we survey recent results (mostly since 2004) relevant to the CH/π hydrogen bond: crystal conformation, packing and host/guest chemistry (section 3). Section 4 summarizes the results obtained by crystallographic database (CSD and PDB) analyses. In section 5, several topics in related fields (selectivity in organic reactions, surface chemistry, structural biology, drug design and high-level ab initio calculations of protein/substrate complexes and natural organic compounds) are introduced, and in the final part we comment on the prospects of this emerging field of chemistry.
489 citations
TL;DR: In the title compound, C20H12BrFO2S, the O atom and the phenyl group of the Phenylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment; the phenol ring is nearly perpendicular to this plane.
Abstract: In the title compound, C20H12BrFO2S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment; the phenyl ring is nearly perpendicular to this plane [dihedral angle = 86.98 (6)°]. The 4-bromophenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 1.56 (8)°. The crystal structure features aromatic π–π interactions between the furan and phenyl rings of neighbouring molecules [centroid–centroid distance = 3.506 (3) A], and an intermolecular C—H⋯π interaction. The crystal structure also exhibits a short intermolecular S⋯S contact [3.2635 (8) A].
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TL;DR: L Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known.
Abstract: Computer Program Abstracts The category Computer Program Abstracts provides a rapid means of communicating up-to-date information concerning both new programs or systems and significant updates to existing ones. Following normal submission, a Computer Program Abstract will be reviewed by one or two members of the IUCr Commission on Crystallographic Computing. It should not exceed 500 words in length and should follow the standard format given on page 189 of the June 1985 issue of the Journal [J. Appl. CrysL (1985). 18, 189190] and on the World Wide Web at http://www.iucr. ac. uk/journals/jac/software/. Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known. J. App/. CrysL (1997). 30, 565 ORTEP-3 for Windows a version of ORTEP-III with a Graphical User Interface (GUI)
19,468 citations
Additional excerpts
...Data collection: SMART (Bruker, 2004); cell re®nement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), POV-Ray for Windows (The POV-Ray Team, 2004), WinGX (Version 1.64.05; Farrugia, 1999) and MERCURY for Linux (Taylor & Macrae, 2001; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2003)....
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...…solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), POV-Ray for Windows (The POV-Ray Team, 2004), WinGX (Version 1.64.05; Farrugia, 1999) and MERCURY for Linux (Taylor & Macrae,…...
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TL;DR: The category Computer Program Abstracts provides a rapid means of communicating up-to-date information concerning both new programs or systems and signi®cant updates to existing ones.
Abstract: The category Computer Program Abstracts provides a rapid means of communicating up-to-date information concerning both new programs or systems and signi®cant updates to existing ones. Following normal submission, a Computer Program Abstract will be reviewed by one or two members of the IUCr Commission on Crystallographic Computing. It should not exceed 500 words in length and should follow the standard format given on page 189 of the June 1985 issue of the Journal [J. Appl. Cryst. (1985). 18, 189± 190] and on the World Wide Web at http://www.iucr. org/journals/jac/software/. Lists of software presented and/or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known.
18,151 citations
"2H-Thiochromene-2-thione" refers methods in this paper
...…(Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), POV-Ray for Windows (The POV-Ray Team, 2004), WinGX (Version 1.64.05; Farrugia, 1999) and MERCURY for Linux (Taylor & Macrae, 2001; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek,…...
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TL;DR: In this paper, the role of CH π interaction in the conformation of organic compounds was examined with the use of the Cambridge Structural Database (CSDB) with the aim to examine the role played by CHπ interaction in organic compounds.
214 citations
"2H-Thiochromene-2-thione" refers background in this paper
...In addition, the molecules are stabilized by a weak CÐH interaction (Table 2) of 2.930 (17) AÊ , belonging to region 3 as categorized by Umezawa et al. (1999)....
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TL;DR: Several substitutions at the 3 position of the coumarin core conferring similar antagonism of gyrase in vitro resulted in substantially different inhibitory activities for E. coli, suggesting that these moieties at the3 position affect drug access to the intracellular target.
Abstract: Novobiocin, coumermycin A1, and clorobiocin, structurally related compounds that antagonize the B subunit of the essential bacterial enzyme DNA gyrase, were compared with 18 of their analogs for the inhibition of Escherichia coli DNA gyrase supertwisting activity in vitro and of bacterial multiplication. This family of compounds has a 4-hydroxy-8-methylcoumarin core substituted in the 7 and 3 positions. Important for enzyme inhibition in vitro is a 7 ether linkage to a 3'-substituted noviose sugar. The 3'-ester-linked 5-methylpyrrole, found in the coumermycin series, conferred at least 10-fold more inhibitory activity than did the similarly linked amide, found in the novobiocin series; lack of the pyrrole and amide results in the loss of inhibitory activity. Of many aryl and alkyl substituents linked as an amide at the 3 position, the 4-hydroxyl-3-(3-methyl-2-butenyl)benzoic acid moiety, found in novobiocin and clorobiocin, and the reduplication of the coumarin-noviose-5-methylpyrrole, found in coumermycin A1, were most effective in gyrase inhibition. In vivo, the ability of these compounds to inhibit the growth of E. coli varied greatly. The enhanced inhibition of gyrase in vitro conferred by a 5-methylpyrrole relative to an amide in the 3'-noviose position was reflected in inhibition of bacterial multiplication. Several substitutions at the 3 position of the coumarin core conferring similar antagonism of gyrase in vitro resulted in substantially different inhibitory activities for E. coli, suggesting that these moieties at the 3 position affect drug access to the intracellular target. This target was shown for isobutyryl PNC-NH2 (PNC-NH2 is 3-amino-4-hydroxy-8-methyl-7-[3-O-(5-methyl-2-pyrrolylcarbonyl)noviosyloxy] coumarin) and confirmed for novobiocin, coumermycin A1, and clorobiocin to be in the B subunit of DNA gyrase.
140 citations
"2H-Thiochromene-2-thione" refers background in this paper
...Substi- tuted coumarin derivatives ®nd application in the dye industry (Hooper et al., 1982; Morris & Russell, 1971) and with regard to laser dyes (Khalfan et al., 1987; Nemkovich et al., 1997), based on the fact that these compounds show state-dependent variation in the static dipole moment....
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