Hydrogen bonding in labdane diterpenoids, labda-7,12(E),14-triene-17-oic acid and labda-12(Z),14,17-triene-18-oic acid |
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| Authors: | Sophon Roegsumran Nongnuj Jaiboon Narongsak Chaichit Damrong Sommit Duangpen Pattamadilok Chaiyo Chaichantipyuth Amorn Petsom |
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| Institution: | (1) Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand;(2) Department of Physics, Faculty of Science and Technology, Thammasat University at Rangsit, Pathumthani, 12121, Thailand;(3) Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, 10330, Thailand |
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| Abstract: | Two labdane diterpenoids, labda-7,12(E),14-triene-17-oic acid (1) and labda-12(Z),14,17-triene-18-oic acid (2), C20H30O2, have been isolated from Croton oblongifolius. Both 1 and 2 crystallized in the monoclinic system, space group C2, with cell dimensions of a = 21.912(1) Å, b = 7.4002(4) Å, c = 11.5079(7) Å,  = 101.999(1)o and a = 21.308(2) Å, b = 11.9067(9) Å, c = 7.5606(6) Å, = 100.763(1)o, respectively. Compound 1, a rare example of carboxylic group bound to a cyclohexene ring, forms an infinite intermolecular hydrogen-bonded polymer O1  O2(–x + 1/2, y + 1/2, –z + 2) 2.697(2) Å], whereas molecules of compound 2 are linked to form an asymmetric hydrogen-bonded dimer O1 O2(–x, y, –z) 2.657(3) Å]. |
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| Keywords: | Crystal structure labdane diterpenoid Croton oblongifolius hydrogen bonding |
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