Crystal structure and conformational analysis of 1-[N-(tert-butoxycarbonyl)amino]-2-hydroxymethylcyclopropane-1-carboxylic acid (CROSBI ID 612618)
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Podaci o odgovornosti
Cetina, Mario ; Hergold-Brundić, Antonija ; Raos, Nenad ; Žuža-Mak, Lora
engleski
Crystal structure and conformational analysis of 1-[N-(tert-butoxycarbonyl)amino]-2-hydroxymethylcyclopropane-1-carboxylic acid
The compound crystallizes as centrosymmetric hydrogen bonded R22(8) dimer with O1...O2 distance of 2.621(3) Å and O1-H...O2 angle of 176(1)o. The carboxyl dimer exists in a state of disorder [C-O bonds in the carboxyl group are equal in length: C4-O2 = 1.264(2) ; C4-O1 = 1.258(3) Å]. In the crystal structure was also observed the intramolecular H-bond O5...O3 [2.750(2) Å ; 157(3)o], and intermolecular H-bond N1...O5 [2.874(3) Å ; 174(2)o] forming infinite chain along the b axis. The intermolecular H-bond C2...O2 [3.395(3) Å ; 143(1)o] forms ten-membered ring of R22(10) type, which geometry centre coincides with a crystallographic centre of inversion. The molecules are additionally connected by very weak intermolecular hydrogen bond C3...O3 [3.501(3) Å ; 165(1)o]. By using the model of overlapping spheres (OS method) for finding the low-energy conformations [1] 25 conformations of the title compound were obtained from the initial structure (minimized crystal conformation). The energy of the initial conformation is 1.2 kJ mol-1 above the lowest energy conformation, and 15.1 kJ mol-1 below the highest energy conformation. The crystal and initial conformation differ in the position of the carboxylic group (3.3° and 77.9°, respectively, for O1-C4-C1-N1), while the other torsion angles do not differ significantly (the maximal difference is 21.1°). [1] Raos, N., J. Comput. Chem. 21 (2000) 1353.
crystal structure; 1-amino-1-carboxylic acid derivatives; hydrogen bonds; conformation analysis
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Podaci o prilogu
71-71.
2003.
objavljeno
Podaci o matičnoj publikaciji
XVIII. hrvatski skup kemičara i kemijskih inženjera
Zrnčević, Stanka
Zagreb: Hrvatsko društvo kemijskih inženjera i tehnologa (HDKI) ; Hrvatsko kemijsko drustvo ; Hinus
953-6894-08-4
Podaci o skupu
XVIII.Hrvatski skup kemičara i kemijskih inženjera,
poster
16.02.2003-19.02.2003
Zagreb, Hrvatska