Crystal structures of two substituted key intermediates of phenothiazine derivatives |
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Authors: | Kattamuri Chandra Mohan Krishnan Ravikumar Meera M. Shetty |
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Affiliation: | (1) Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad, 500 007, India;(2) Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, 500 007, India |
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Abstract: | The key intermediates, in the synthesis of phenothiazines, 5-hydroxy-5-methyl 3(phenyl) 2,4-N-dimethylcarbamoyl cyclohexanone, C17H22O4N2 (I), and 5-hydroxy-5-methyl 3(2-methylphenyl) 2,4-N-dimethylcarbamoyl cyclohexanone, C18H24O4N2 (II), contain essentially substituted cyclohexanone rings in chair conformation with approximately perpendicular oriented phenyl rings. The carbamoyl groups are aligned in opposite directions to facilitate the formation of intramolecular C–HO interaction and O–HO hydrogen bonding. The molecules are linked in helical fashion by an N–HO type intermolecular hydrogen bonding framework. Crystal data: [I], orthorhombic, space group Pbca, a = 9.278(1), b = 19.094(2), c = 19.802(2) Å, V = 3508.0(6) Å3, Z = 8 and d = 1.206 Mg m–3, R = 0.074 (wR = 0.137) for 208 parameters and 1190 observed reflections with I 2 (I); [II], monoclinic, space group P21/n, a = 10.523(1), b = 9.005(1), c = 19.771(2) Å, = 94.96(6)°, V = 1866.5(3) Å3, Z = 4 and d = 1.183 Mg m–3, R = 0.062 (wR = 0.131) for 217 parameters and 2276 observed reflections with I 2 (I). |
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Keywords: | Crystal structure cyclohexanone derivatives conformation hydrogen bonds |
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