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1 - -- (// : // : ) -- - () -- - :. / (:: ). X IR C2/c. K b = / () Å c = / () Å β = / (). / R.a = / () Å -. - π-π N H O.. -- :.[] -.[]..[]..9H 2 O tarth 2 [(dmphenh)(tarth)] [] -- - dmphen acr (acrh)(btch 2 ).H 2 O π-π -.[-]...[-] zderik@yahoo.com : : + :

2 (aacr) - (acrah) -- mg. : :. ml ( mmol) - ( mmol) mg ml ml mg... C..... C. IR. C 27 H 19 N 3 O 2 IR. cm 1. [] -- [] - -- phen [] -- btch 2 (phenh)(tarth).3h 2 O pydch 2 (pydah 2 )(pydc) pyda - tata (tatah) 2 (pydc) (tatah 2 )(pydc). [] () IR. Perkin-Elmer RXI (IR). KBr (- cm 1 ). Heraus CHN Pro Bruker APEX / Å Mo-Kα ) II. (K.[] SAINT APEX2 [] SADABS. [] SHELXTL (aacrh) + (acra)

3 ....(aacrh) + ( acra) C % / H % / N % / % / % / % / --. (aacr) - (acrah) ().( ). -. C = O. cm 1. COO cm 1 - cm 1 NH 2.. cm 1 C 27 H 19 N 3 O 2 X (aacrh) + ( acra) C 13 H 11 N 2 C 14 H 8 NO 2 / ( ) / / / ( ) C2/c / () / () / () / () /() / -19<=h<=19, -17<=k<=18, -24<=l<=24 / /. / a (Å) b (Å) c (Å) β ( ) (Å 3 ) (g/cm 3 ) () h, k, l R 1 WR 2 R int θ

4 O1 C27 O2 C27 N1 C6 N1 H1N N1 H1N' N2 C13 N2 C12 N2 H2N N3 C25 N3 C26. (aacrh) + ( acra). (aacrh) + ( acra) ( ) (Å) (Å) / () / () / () / () / () / () / () / () / () / () C6 N1 H1N C6 N1 H1N' H1N N1 H1N' C13 N2 C12 C13 N2 H2N C12 N2 H2N C25 N3 C26 O2 C27 O1 O2 C27 C19 O1 C27 C19 (º) ( Å) (aacrh) + ( acra) D H A D H H A D A D H A N1 H1N' O1 i /() /() /() N1 H1N O1 ii /() /() /() N2 H2N O2 iii /() /() /() (i) x, y-1, z; (ii) -x, y-1, -z+1/2; (iii) -x, -y+1, -z+1 / () / () / () / () / () / () / () / () / () / () / () / () / () -. π π π π - / ()Å - / ()Å π π N H O. C2/c...

5 ... [3] Braga D., Maini L., Paganelli F., Tagliavini E., Casolari S., Grepioni F., "Organometallic building blocks for crystal engineering. Synthesis, structure and hydrogen bonding interactions in [Fe(η 5 - C 5 H 4 CH 2 (CH 3 )OH) 2 ], [Fe(η 5 -C 5 H 3 (CH 3 )COOH) 2 ], [Fe(η 5 -C 5 H 4 CH(CH 3 )NH(η 5 -C 5 H 4 CH(CH 3 ))] and in the diaminecyclohexane salt [Fe(η 5 - C 5 H 4 COO) 2 ] 2 [(1S,2S)-(NH 3 ) 2 C 6 H 10 ] 2+ 2[H 2 O] ", Journal of Organometallic Chemistry (2001) [4] Eppel S., Bernstein J., "Statistical survey of hydrogen-bond motifs in crystallographic special symmetry positions, and the influence of chirality of molecules in the crystal on the formation of hydrogen-bond ring motifs", Acta Crystallographica B64 (2008) [5] Derikvand Z., Dorosti N., Hassanzadeh F., Shokrollahi A., Mohammadpour Z., Azadbakht A., "Three new supramolecular compounds of copper (II), cobalt (II) and zirconium (IV) with pyridine- 2,6-dicarboxylate and 3,4-diaminopyridine: Solid and solution states studies", Polyhedron 43 (2012) [6] Steed J. W., Atwood J. L., " Supramolecular Chemistry", J. Wiley & sons, (2000). [7] Krishnamohan Sharma C. V., "Crystal Engineering Where Do We Go from Here?", Crystal Growth & Design 2 (2002) [8] Desiraju G. R., " Crystal engineering: Outlook and prospects ", Current Science, 81 (2001) [9] Desiraju G. R., Steiner T.," The Weak Hydrogen Bond Structural Chemistry and Biology", Oxford, (1999). [10] Prodić B. K., Štefanić Z., Žinić M., "Hydrogen Bonding and Molecular Assemblies", Croatica Chemica Acta 77(3) (2004) [11] Derikvand Z., Olmstead M. M., "Bis(2,9- dimethyl-1,10-phenanthrolin-1-ium) hydrogen (S,S)-tartrate nonahydrate", Acta Crystallographica E67 (2011) o87 o88. [12] Derikvand Z., Aghabozorg H., Attar Gharamaleki J., "Acridinium 3,5- dicarboxybenzoate monohydrate", Acta Crystallographica. E65 (2009) o1173. [13] Derikvand Z., Olmstead M. M., "1,10- Phenanthrolin-1-ium hydrogen (S,S)-tartrate trihydrate and a correction", Acta Crystallographica E66 (2010) o185. [14] Moghimi A., Ranjbar M., Aghabozorg H., Jalali F., Shamsipur M., Yap G. P. A., Rahbarnoohi H., "A novel pyridine containing self- N H O. O2 O1 O1. - O2 C27 O1 C27 D.( ) D A H A H A. / () Å / () Å D A.( ). N H O C H N / Å H A C. - H π C10-H10A. C14-C18/C26. / Å H π (CCDC) ( [1] Perpétuo G.J., Gonçalves R. S., Janczak J., "Supramolecular hydrogen-bonding network in 1- (diaminomethylene)thiouron-1-ium 4- hydroxybenzenesulfonate crystal" Journal of Molecular Structure 1096 (2015) [2] Kaur G., Singh S., Sreekumar A., Choudhury A. R., "The evaluation of the role of C H F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond" Journal of Molecular Structure 1106 (2016)

6 [16] Bruker (2007) APEX2, SAINT & SADABS Bruker AXS Inc., Madison, Wisconsin, USA. [17] Sheldrick G.M., A short history of SHELX, Acta Crystallographica A64 (2008) assembling system: synthesis, characterization, X- ray crystal structure, 13C solid phase NMR and solution studies", Journal of Molecular Structure 605 (2002) [15] Sharif M. A., Aghabozorg H., Shokrollahi A., Kickelbic G., Moghimi A., Shamsipur M., "Novel Proton Transfer Compounds Containing 2,6-Pyridinedicarboxylic Acid and Melamine and Their Pb II Complex: Synthesis, Characterization, Crystal Structure and Solution Studies", Polish Journal of Chemistry 80 (2006)

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