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Crystal structures of N -[(4-phenyl ­ thia ­ zol-2-yl)carbamo ­ thio ­ yl]benzamide and N -{[4-(4-bromo ­ phen ­ yl)thia ­ zol-2-yl]carbamo ­ thio ­ yl}benzamide from synchrotron X-ray diffraction

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ABSTRACT

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamo­thio­yl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thia­zole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thia­zol-2-ylcarbamo­thio­yl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromo­phenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol­ecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] inter­actions.

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The crystal structure of (II). Dashed lines indicate the intra­molecular N—H⋯O and inter­molecular N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary inter­molecular S⋯S and S⋯Br inter­actions.
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fig4: The crystal structure of (II). Dashed lines indicate the intra­molecular N—H⋯O and inter­molecular N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary inter­molecular S⋯S and S⋯Br inter­actions.

Mentions: The situation in the case of (II) is quite different. The mol­ecules of (II) form a three-dimensional framework mediated by the N2—H2⋯Br1i and C13—H13⋯O1ii hydrogen bonds (Table 2 ▸, Fig. 4 ▸) as well as the secondary S1⋯Br1iii [3.3507 (11) Å] and S2⋯S2iv [3.4343 (14) Å] inter­actions [symmetry codes: (i) x, −y + 1, z − ; (ii) −x + 1, −y, −z + 1; (iii) x, −y + 1, −z + 1; (iv) −x + , y + , −z + ; Fig. 4 ▸]. It should be pointed out that the secondary inter­molecular S⋯Br and S⋯S inter­actions in (II) are significantly stronger than the inter­molecular hydrogen bonds and, consequently, structure-forming.


Crystal structures of N -[(4-phenyl ­ thia ­ zol-2-yl)carbamo ­ thio ­ yl]benzamide and N -{[4-(4-bromo ­ phen ­ yl)thia ­ zol-2-yl]carbamo ­ thio ­ yl}benzamide from synchrotron X-ray diffraction
The crystal structure of (II). Dashed lines indicate the intra­molecular N—H⋯O and inter­molecular N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary inter­molecular S⋯S and S⋯Br inter­actions.
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fig4: The crystal structure of (II). Dashed lines indicate the intra­molecular N—H⋯O and inter­molecular N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary inter­molecular S⋯S and S⋯Br inter­actions.
Mentions: The situation in the case of (II) is quite different. The mol­ecules of (II) form a three-dimensional framework mediated by the N2—H2⋯Br1i and C13—H13⋯O1ii hydrogen bonds (Table 2 ▸, Fig. 4 ▸) as well as the secondary S1⋯Br1iii [3.3507 (11) Å] and S2⋯S2iv [3.4343 (14) Å] inter­actions [symmetry codes: (i) x, −y + 1, z − ; (ii) −x + 1, −y, −z + 1; (iii) x, −y + 1, −z + 1; (iv) −x + , y + , −z + ; Fig. 4 ▸]. It should be pointed out that the secondary inter­molecular S⋯Br and S⋯S inter­actions in (II) are significantly stronger than the inter­molecular hydrogen bonds and, consequently, structure-forming.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamo­thio­yl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thia­zole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thia­zol-2-ylcarbamo­thio­yl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromo­phenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol­ecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] inter­actions.

No MeSH data available.