Karmakar, Sanjib

Talukdar, A N

IACS Institutional Repository

Indian J- P/ivA. 78 (9), 923-925 (2004)’^ Z-.I J  P >Crystal and molecular structure of 4 (4' N, N-dimethylamino) benzylidene-2-phenyloxazolin-5-oneSanjib Karmakar' * and A N Talukdar‘University Science Insirutn^ntation C'cntre (USIC),‘Deparlnient of Physics, Gauhati Uniftrsiiy, (iuwahali 7S1 014, Indi,E-mail sanjibkab(^ediffmail com Received 10 September 2003^ ac(epicd 20 July 2004Vbslract I’he crystal structure o f the title compound, Inis been determined by X-tay diftrachon The bcii/vlidene nn^ A, iheo\a/olin fi-one ling system B and the attached phenyl ring C of the title compound (II) arc almost planar having interplanai angles between A and B jml thai Ivtween B and C arc 4.10  ^ and 3 03 ° respectively The N.N-dimclhyl group is iieaily coplanai with the bcn/ylidene iing plane riteic is nt) inicimolecular hydrogen bond and the molecule is stabilised by the normal van dei Waals interaction in the crystalline assemblyKe\words (Yyslal structure, N,N-dimethyI, van der Waals' interactionP \(’S Nos. 61.10 N /, 61 66.Hq1. IntroductionOxazoline compounds which form acyl-enzym e com plexes with papain, are o f medicinal importance in biology. Although the tirst alkyloxazoline was reported by Gabriel [I j, the crystal struciures o f this class o f  com pounds are limited because few1.4 (4,2-dinitro)benzylidene-2-phenyloxazolin-5'oneII. 4 (4/NJvJ-dimethylamino)benzylidene-2-phenyloxazoiine-5-one'corresponding Authoro f the known oxazoline arc solid at nxjrn Icmperature The crystal structure of 4-(4-2-dinitro) benzylidene-2-phenyloxazohn-5-one (1) has been reported in literature 12|. Cry.stallographic study ol the analogous 4 -(4 -N ,N - d im ethylam ino) bcnzyIidcne-2- phenyloxazoline-5-one (II) has been reported m this paper.2* Experimental details0.05  m ole o f  hipparic acid was d isso lved  in 100 ml. of dimethylformaide saturated with sulfurtrioxidc. To this .solution 0.05 mole o f (4 N,N-dimcthyi) benzyldehyde was added at room temperature and stirred in a magnetic stincr for 30 minutes. The red precipitate obtained was recovered and recrystal I i.sed from 95% of ethanol. Preliminary X-ray study revealed monocimic crystal system. The .systematic absences established the space group as F2 / c \  The unit cell parameters were refined by least squares method on the basis o f  25 independent high angle reflections. The data were corrected for Lorentz and polarisation effects, but no absorption correction was made.3. Structure solution and refinementThe structure was solved by direct methods using the program SHELXS 97 [3] and refined on F- using the program SHELXL97 [41 Full matrix least-squares refinem ent with anisotropic temperature factors to non-hydrogen atoms led to the R value©20041ACS924 Sanjih Karniakar and A N TalukdarTable 1» Crystal data for the title compoundChemical formula O,Molecular weight 292 32Ciystal system monnclinicSpace group P 2, !cLattice parameters a = 12 177(4) A h ^ 3 900( 1) A r = 30 044(8) A b 10I.r70(I(»"’Volume 14<)6.1(7) A^/ 4Measuied density, Dm 1 320 Mg in ^Calculated density D \ 1 324 Mg m-^Temperature 203 KCrystal si/e 0 45 X 0 IN X 0 14 mm*Crystal colour PinkRadiation C'uKaWavelength 1 5418 AAbsorption coefficient ( mu) 0 70 mm •0 ( Theta) max. 68''Index ranges 0 < h < 14, 0 < k < 4, 36 1 < 36No of reflections measured 2325No. o f unique reflections . 2280No. o f observed reneciions 1006 [1 > 2a (D)0 078F (000) 616Goodness of fit 1 134Final R 0 0787K 0 2073Table 2. Practional atomic cuoidinates for non hydiogcn eqUiVdicnt iSOtrOpiC diSpiaCcriicnt paraiiiCiCrs ( A")atomso f  0.0882. The final R value was 0.0787 with the inclusion o f the hydrogen atoms from the difference Fourier maps with isotropic thermal parameters. The peak heights in the final difference Fourier map were in the range o f  0 .28 to -0 .3 3  e T h e  atomic scattering factors used were taken from the International Table for X-ray Crystallography Vol. IV [5J. The molecular geometry was calculated using the program SHELXL 97 [4J. The crystal data and the fractional coordinates and equivalent isotropic thermal parameters for all non-hydrogen atoms are shown in Table 1 and Table 2 respectively.4. Result and discussionThe ORTEP f6] view o f  the m olecule with atom numbering schem e and the packing o f  the m olecule are shown in Figure I and Figure 2 respectively. The m olecule consists o f  an essentially planner oxazolin-5-one moiety linked to phenyl and benzylideneK- ( 1 / 3 ) S S « V> J /X y z I 'u )01 0 2152(2) 0 7461(7) 0 12868(8) 0 05SSf0 2 0 2052(2) 0 5231(9) 0 06047(9) 0  07 : '^ . ( . ,(\3 0 7700(3) 1 1018(0) 0 .07764(8) 0N4 0 3002(2) 0 .0 5 6 5 (8 ) 0 14226(0) 0  0 4 K : i ,-;,C5 0 5540(3) 0 0142(8) 0 07425(7) 0  0 4 U , ( ^  1N6 0.8800(2 ) I 1073(0) 0 .07051(6) 0  0S7f,(M,C7 0.6102(3 ) 0 .8396(5 ) 0 04014(7) 0  o i s n u i ,C8 0 7241(3) 1.1841(0) 0 11209(0) 0  0 4 60 (U .CO 0 7192(3) 0 0369(8) 0 .04003(8) 0 04X7in,CIO 0 4400(3) 0 .7050(0 ) 0 07120(0) 0  ()4S(,!nt('1 1 0 2767(3) 1 0075(0) 0 19061(8) 0  04K^^M;Cl 2 0 6142(3) 1 0846(0) 0 11036(0) 0  l)4^7iC13 0 3715(3) 0 8203(0) 0 10010(7) 0 04())<w,C14 0 2502(3) 0 6605(8) 0  0 0 1 1 0 ( 0 ) 0 OS ■C15 0 2000(3) 0 0006(8) 0-15700(8) 0 ()47 () !‘>Cl 6 0 .3504(3) 1 1631(0) 0 23000(0) 0 O.SSS; * .C17 0.3406(4 ) 1 2517(8) 0 27074(0) 0 007():‘>'C18 0.1543(4 ) 1 0355(0) 0 25182(8) 0 0 ( , / 0 ( S ;CIO 0 1737(3) 0 0426(8) 0 21104(0) 0  0 ^ S 0 " tC20 0 0528(4) I 3575(9) 0 1182(2) 0 (K) () l i ' ' )C21 0 .2377(4 ) 1 1862(8) 0 28157(7) 0  ( ) 6 7 4 r ) -C22 0 9452(4) 1 1234(7) 0 0437(2) 0  n()7'^d>!rings v ia  C-C and CII groups. The torsion angles (Tabic anthat the m olecule is almost planar; the maximum deviation o1 iin atom (C3) is 0.026(4) A . The planarity o f the molecule is presumedFigure 1. ORTEP diagram of the molecule with atom numbering schcnit the H-atoms are shown by circles.C r y s t a l  a n d  m o l e c u l a r  s t ru c tu r e  o f  4  (4 '  N, N - d im e th y l a m m o )  e tc  'Ribic 3. Selected bond di!>lanceti (A), angles (") and the torsion angles (“) and their esd's m parenthesis925N4 -  C13 = 1.389(4) N4 -  CIS = 1.284(4) N6 -  C3 = 1 372(4) ('14 -  0 2  = I 196(3) N6 -  C20 = I 442(5) NO -  C22 = 1 441(6)C22 ■ NO -  C20 = 1 1 7  9(4) C22 -  NO -  C3 = 120.8(3) C20 -  NO -  (’3 121.2(3)01 -  CIS -  CM = 116.8(3) N4 -  CIS -  Cl I = 128.0(3) N4 -  CIS - OI = 1155(2)C22 -  NO -  C3 -  ('8 -  177 9(4)C20 -  NO -  C.3 - C9 = I77.8(.3)C'1.3 -  n o  -  C5 - C l ■■ 170 (>(5) C5 -  CIO -  C13 -C I4  = -  177 7(4) (’10 - (’ll -  CIS -  Ol = 178 0(3) (’19 -  Cl 1 - CIS -  N4 -  179 3(4),1 be due to conjugation effect. The dihedral angle between the ,vizolin-5-one moiety (N4,C 13,C 14 .0 1  ,C 15,02) and the attached ihenyl ring (C 1 i ,C 16,C17.C21,C 18.C19) is 3 .0(2)“ while that iciwcen the o x a z o l in - 5 - o n e  and th e b e n z y lid e n e  ("i,r7.(^.C3,C8,C 12) parts is 4.1 (2)'’. The bond lengths and bond iieles (Table 3) o f  the title com pound are comparable to tho.se ihscrved in related oxazolin-5-one compounds [ 7-10]. The crystal iiiuturc IS stabilised by van der Waals' contacts.AcknoH'ledgmentWfelhank All India InsliUite of Medical sScicnccs ( AIlMsS), New Delhi-100 029, for collecting the intensity data for the sample and Dr. P. J. Das, Department of Chemistiy, Gaiihati University, for supplying the crystal.References'[11 (Jabncl liv! 22 2220 (1SS9)[2J A W Han.son A(ta Crwi S04 (1077)[3 I G M Sheldiick Sllf 'J.XS 97 Pioi^iam for the Solution of Ciystal Stnuturcs (University of Gollinjzcn, (’icrmany) (19S6)141 (i M Sheldnck SnELXf^~^>7 Proi^mm foi iliv Xcfincnicnt of ( rv.stui Strurtnrc.s (University nf Gottingen, Geimany) (1997)[51 fntcrnciiKmaf 'lahlvs for X-ra\> ( 7 (BnmmghaniKynoch Pte.ss) IV (1974)C' K Johnson ORThr fl. Kepon OKNL (Oak Rulge National Laboratory. Tennessee, USA) (1976)A C Willis, A L J Beckwith and M J To/ei Acta Ct\'M C'47 2276 (1991)16J|71IHlifiurt* 2, Flacking of the molecule viewed along the b axis, ihc H-atoms arc omitted for clarity[) Sccback, M Boes, W B Nael and W B Sdiwei/ci J Am ( hem. Sor 105 539 0 (1 9 8 3 )[9) S Karady. J S Amato and I M Weinstock leiraliedron le ft  25 4337 (1984)[101 7 A Webet, T Mact/kc and 17 Sccback ficiv (him Attn 69 1365(1986)

Crystal and Molecular Structure of 4 (4' N, N-Dimethylamino) Benzylidene-2- Phenyloxazolin-5-One

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Crystal and Molecular Structure of 4 (4' N, N-Dimethylamino) Benzylidene-2- Phenyloxazolin-5-One

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