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2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione

In the title 1,2,4-triazine derivative, C(17)H(19)N(3)O(3), the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclo­hex-3-en-1-ylmeth­oxy)methyl residue [N—N—C—O torsion ang...

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Autores principales: El-Brollosy, Nasser R., Attia, Mohamed I., El-Emam, Ali A., Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379356/
https://www.ncbi.nlm.nih.gov/pubmed/22719554
http://dx.doi.org/10.1107/S1600536812021198
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author El-Brollosy, Nasser R.
Attia, Mohamed I.
El-Emam, Ali A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet El-Brollosy, Nasser R.
Attia, Mohamed I.
El-Emam, Ali A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort El-Brollosy, Nasser R.
collection PubMed
description In the title 1,2,4-triazine derivative, C(17)H(19)N(3)O(3), the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclo­hex-3-en-1-ylmeth­oxy)methyl residue [N—N—C—O torsion angle = 71.6 (5)°], so that the mol­ecule has an ‘L’ shape. Supra­molecular chains along [001] are formed in the crystal via N—H⋯O hydrogen bonds where the acceptor O atom is the ether O atom. The adjacent carbonyl O atom forms a complementary C—H⋯O contact resulting in the formation of a seven-membered {⋯HNCO⋯HCO} heterosynthon; the second carbonyl O atom forms an intra­molecular C—H⋯O contact. Chains are connected into a supra­molecular layer in the ac plane by π–π inter­actions [ring centroid–centroid distance = 3.488 (3) Å]. The central atom in the –CH(2)CH(2)C(H)= residue of the cyclo­hexene ring is disordered over two sites, with the major component having a site-occupancy factor of 0.51 (2).
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spelling pubmed-33793562012-06-20 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione El-Brollosy, Nasser R. Attia, Mohamed I. El-Emam, Ali A. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title 1,2,4-triazine derivative, C(17)H(19)N(3)O(3), the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclo­hex-3-en-1-ylmeth­oxy)methyl residue [N—N—C—O torsion angle = 71.6 (5)°], so that the mol­ecule has an ‘L’ shape. Supra­molecular chains along [001] are formed in the crystal via N—H⋯O hydrogen bonds where the acceptor O atom is the ether O atom. The adjacent carbonyl O atom forms a complementary C—H⋯O contact resulting in the formation of a seven-membered {⋯HNCO⋯HCO} heterosynthon; the second carbonyl O atom forms an intra­molecular C—H⋯O contact. Chains are connected into a supra­molecular layer in the ac plane by π–π inter­actions [ring centroid–centroid distance = 3.488 (3) Å]. The central atom in the –CH(2)CH(2)C(H)= residue of the cyclo­hexene ring is disordered over two sites, with the major component having a site-occupancy factor of 0.51 (2). International Union of Crystallography 2012-05-19 /pmc/articles/PMC3379356/ /pubmed/22719554 http://dx.doi.org/10.1107/S1600536812021198 Text en © El-Brollosy et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
El-Brollosy, Nasser R.
Attia, Mohamed I.
El-Emam, Ali A.
Ng, Seik Weng
Tiekink, Edward R. T.
2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title_full 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title_fullStr 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title_full_unstemmed 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title_short 2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione
title_sort 2-[(cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2h,4h)-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3379356/
https://www.ncbi.nlm.nih.gov/pubmed/22719554
http://dx.doi.org/10.1107/S1600536812021198
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