Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione
Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in N,N -dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[ b ]phenazine-6,11-dione. This is a remarkable example...
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| Veröffentlicht in: | Crystallography reports 2018-11, Vol.63 (6), p.925-929 |
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| creator | Yıldız, M. Bayrak, N. Yıldırım, H. Sahin, M. Tuyun, A. F. |
| description | Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in
N,N
-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[
b
]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[
b
]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C
22
H
20
N
2
O
3
, crystallizes in the sp. gr.
P
,
Z
= 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å. |
| doi_str_mv | 10.1134/S1063774518060317 |
| format | Article |
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N,N
-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[
b
]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[
b
]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C
22
H
20
N
2
O
3
, crystallizes in the sp. gr.
P
,
Z
= 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å.</description><identifier>ISSN: 1063-7745</identifier><identifier>EISSN: 1562-689X</identifier><identifier>DOI: 10.1134/S1063774518060317</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Aniline ; Atomic properties ; Crystal structure ; Crystallography and Scattering Methods ; Crystals ; Diketones ; Hydrogen bonds ; Naphthalene ; Physics ; Physics and Astronomy ; Single crystals ; Sodium azides ; Structure of Organic Compounds ; X-ray diffraction</subject><ispartof>Crystallography reports, 2018-11, Vol.63 (6), p.925-929</ispartof><rights>Pleiades Publishing, Inc. 2018</rights><rights>Copyright Springer Science & Business Media 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c305t-ac61b2559937646e8397259cffdd8d30795f27bf9c3abb803f41bc6cd49e333e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1063774518060317$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1063774518060317$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Yıldız, M.</creatorcontrib><creatorcontrib>Bayrak, N.</creatorcontrib><creatorcontrib>Yıldırım, H.</creatorcontrib><creatorcontrib>Sahin, M.</creatorcontrib><creatorcontrib>Tuyun, A. F.</creatorcontrib><title>Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione</title><title>Crystallography reports</title><addtitle>Crystallogr. Rep</addtitle><description>Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in
N,N
-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[
b
]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[
b
]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C
22
H
20
N
2
O
3
, crystallizes in the sp. gr.
P
,
Z
= 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å.</description><subject>Aniline</subject><subject>Atomic properties</subject><subject>Crystal structure</subject><subject>Crystallography and Scattering Methods</subject><subject>Crystals</subject><subject>Diketones</subject><subject>Hydrogen bonds</subject><subject>Naphthalene</subject><subject>Physics</subject><subject>Physics and Astronomy</subject><subject>Single crystals</subject><subject>Sodium azides</subject><subject>Structure of Organic Compounds</subject><subject>X-ray diffraction</subject><issn>1063-7745</issn><issn>1562-689X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEUxIMoWKsfwFvBi4LRvPzPwYMUtYLgoQqCyLLJJtpSNzXZhW4_vVsqeBBPb2DmNw8GoWMgFwCMX06BSKYUF6CJJAzUDhqAkBRLbV52e93beOPvo4Oc54QQrYEP0NU4dbkpF6Npk1rXtMmPYhhRfDrxq24RV92Z9fU6vtq35Yevy_Ws9lieA-BqFmt_iPZCucj-6OcO0fPtzdN4gh8e7-7H1w_YMSIaXDoJlgphDFOSS6-ZUVQYF0JV6YoRZUSgygbjWGmtJixwsE66ihvPGPNsiE62vcsUv1qfm2Ie21T3LwsK3BhBtZR9CrYpl2LOyYdimWafZeoKIMVmpeLPSj1Dt0zus_W7T7_N_0Pfa41ngg</recordid><startdate>20181101</startdate><enddate>20181101</enddate><creator>Yıldız, M.</creator><creator>Bayrak, N.</creator><creator>Yıldırım, H.</creator><creator>Sahin, M.</creator><creator>Tuyun, A. F.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20181101</creationdate><title>Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione</title><author>Yıldız, M. ; Bayrak, N. ; Yıldırım, H. ; Sahin, M. ; Tuyun, A. F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-ac61b2559937646e8397259cffdd8d30795f27bf9c3abb803f41bc6cd49e333e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aniline</topic><topic>Atomic properties</topic><topic>Crystal structure</topic><topic>Crystallography and Scattering Methods</topic><topic>Crystals</topic><topic>Diketones</topic><topic>Hydrogen bonds</topic><topic>Naphthalene</topic><topic>Physics</topic><topic>Physics and Astronomy</topic><topic>Single crystals</topic><topic>Sodium azides</topic><topic>Structure of Organic Compounds</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yıldız, M.</creatorcontrib><creatorcontrib>Bayrak, N.</creatorcontrib><creatorcontrib>Yıldırım, H.</creatorcontrib><creatorcontrib>Sahin, M.</creatorcontrib><creatorcontrib>Tuyun, A. F.</creatorcontrib><collection>CrossRef</collection><jtitle>Crystallography reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yıldız, M.</au><au>Bayrak, N.</au><au>Yıldırım, H.</au><au>Sahin, M.</au><au>Tuyun, A. F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione</atitle><jtitle>Crystallography reports</jtitle><stitle>Crystallogr. Rep</stitle><date>2018-11-01</date><risdate>2018</risdate><volume>63</volume><issue>6</issue><spage>925</spage><epage>929</epage><pages>925-929</pages><issn>1063-7745</issn><eissn>1562-689X</eissn><abstract>Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in
N,N
-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[
b
]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[
b
]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C
22
H
20
N
2
O
3
, crystallizes in the sp. gr.
P
,
Z
= 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1063774518060317</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | SpringerNature Journals |
| subjects | Aniline Atomic properties Crystal structure Crystallography and Scattering Methods Crystals Diketones Hydrogen bonds Naphthalene Physics Physics and Astronomy Single crystals Sodium azides Structure of Organic Compounds X-ray diffraction |
| title | Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione |
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