(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)hydrazinecarbothioamide
نویسندگان
چکیده
In the title compound, C(16)H(13)ClN(4)OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thio-semicarbazide and 2-chloro-benzyl groups, respectively. The near planarity of the isatin and thio-semicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intra-molecular N-H⋯O and N-H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. Aromatic π-π stacking inter-actions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.
منابع مشابه
Diethyl 2-oxo-3-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)butanedioate
The title compound, C(16)H(15)NO(6), crystallizes with two symmetry-independent mol-ecules in the asymmetric unit. The crystal structure is stabilized by inter-molecular C-H⋯O and N-H⋯O hydrogen bonds, and intra-molecular C-H⋯O hydrogen bonds. In addition, the crystal structure exhibits two inter-molecular C-H⋯π inter-actions.
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The mol-ecule of the title compound, C(14)H(10)FN(3)O(3)S, consists of an indole unit and a phenylsulfonyl unit that are disposed in an approximately trans orientation relative to the N-N single bond. Two mol-ecules are arranged about a center of inversion, forming a hydrazide-carbonyl N-H⋯O hydrogen-bonded dimer; the dimers are linked by an indole-sulfonyl N-H⋯O hydrogen bond into a ribbon.
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In the title compound, C(15)H(19)N(5)O(3)S, intra-molecular N-H⋯O, N-H⋯N and C-H⋯S inter-actions occur and the three terminal C atoms of the hexyl group are disordered over two sites with an occupancy ratio of 0.664 (12):0.336 (12). In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur and C-H⋯O bonds link the dimers into chains. A short C=O⋯π contact is also present.
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The solid-state structures of a series of seven substituted 3-methylidene-1H-indol-2(3H)-one derivatives have been determined by single-crystal X-ray diffraction and are compared in detail. Six of the structures {(3Z)-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-2(3H)-one, C(13)H(10)N(2)O, (2a); (3Z)-3-(2-thienylmethylidene)-1H-indol-2(3H)-one, C(13)H(9)NOS, (2b); (3E)-3-(2-furylmethylidene)-1H-indol...
متن کامل2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2-cyanoacetamide
Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl-idene)propane-dial with hydroxyl-amine gives the title compound, C(14)H(14)ClN(3)O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano-acryl-amide unit. The orientation of the acetamide group arises from intra-molecular hydrogen bonding between the...
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