Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols
The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2014-11-01
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| Series: | Acta Crystallographica Section E |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536814022570 |
| _version_ | 1798027055806283776 |
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| author | Matthew R. Carbone Garrick A. Centola Adam Haas Kevin P. McClelland Michael D. Moskowitz Angelo M. Verderame Mikael S. Olezeski Louis J. Papa Stephanie C. M. Dorn William W. Brennessel Daniel J. Weix |
| author_facet | Matthew R. Carbone Garrick A. Centola Adam Haas Kevin P. McClelland Michael D. Moskowitz Angelo M. Verderame Mikael S. Olezeski Louis J. Papa Stephanie C. M. Dorn William W. Brennessel Daniel J. Weix |
| author_sort | Matthew R. Carbone |
| collection | DOAJ |
| description | The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N—H...O=S and C—H...O=S hydrogen bonds link molecules, forming chains along [100], while in (2), similar hydrogen bonds link molecules into chains along [010]. The absolute structures of both compounds were determined by resonance scattering. |
| first_indexed | 2024-04-11T18:45:07Z |
| format | Article |
| id | doaj.art-59b32de7aa9e48ed84662b978948d2df |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-04-11T18:45:07Z |
| publishDate | 2014-11-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-59b32de7aa9e48ed84662b978948d2df2022-12-22T04:08:50ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-11-01701136536910.1107/S1600536814022570su2794Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcoholsMatthew R. Carbone0Garrick A. Centola1Adam Haas2Kevin P. McClelland3Michael D. Moskowitz4Angelo M. Verderame5Mikael S. Olezeski6Louis J. Papa7Stephanie C. M. Dorn8William W. Brennessel9Daniel J. Weix10Department of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USADepartment of Chemistry, 120 Trustee Road, 412 Hutchison Hall, University of Rochester, Rochester, NY 14627, USAThe title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N—H...O=S and C—H...O=S hydrogen bonds link molecules, forming chains along [100], while in (2), similar hydrogen bonds link molecules into chains along [010]. The absolute structures of both compounds were determined by resonance scattering.http://scripts.iucr.org/cgi-bin/paper?S1600536814022570crystal structuresulfinamidediastereomeramino alcoholhydrogen bondingNMRcolumn chromatography |
| spellingShingle | Matthew R. Carbone Garrick A. Centola Adam Haas Kevin P. McClelland Michael D. Moskowitz Angelo M. Verderame Mikael S. Olezeski Louis J. Papa Stephanie C. M. Dorn William W. Brennessel Daniel J. Weix Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols Acta Crystallographica Section E crystal structure sulfinamide diastereomer amino alcohol hydrogen bonding NMR column chromatography |
| title | Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols |
| title_full | Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols |
| title_fullStr | Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols |
| title_full_unstemmed | Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols |
| title_short | Crystal structures of (RS)-N-[(1R,2S)-2-benzyloxy-1-(2,6-dimethylphenyl)propyl]-2-methylpropane-2-sulfinamide and (RS)-N-[(1S,2R)-2-benzyloxy-1-(2,4,6-trimethylphenyl)propyl]-2-methylpropane-2-sulfinamide: two related protected 1,2-amino alcohols |
| title_sort | crystal structures of rs n 1r 2s 2 benzyloxy 1 2 6 dimethylphenyl propyl 2 methylpropane 2 sulfinamide and rs n 1s 2r 2 benzyloxy 1 2 4 6 trimethylphenyl propyl 2 methylpropane 2 sulfinamide two related protected 1 2 amino alcohols |
| topic | crystal structure sulfinamide diastereomer amino alcohol hydrogen bonding NMR column chromatography |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536814022570 |
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