(1E,3E)-4-(tetra-O-acetyl-D-arabino-tetritol-1-yl)-1-(4-tolyl)-1,2-diaza-1, 3-butadiene

o ganic pape s Ac a C ys . (2006). E62, o2811–o2812 doi:10.1107/S1600536806021428 Dia ´nez e al. C 21 H 26 N 2 O 8 o2811 Ac a C ys allog aphica Sec ion E S uc u e Repo s Online ISSN 1600-5368 (1E,3E)-4-(Te a-O-ace yl-D-a abino- e i ol-1-yl)- 1-(4- olyl)-1,2-diaza-1,3-bu adiene Ma ı ´a Jesu ´sDia ´nez, Ma ı ´a Dolo es Es ada and Simeo ´nPe ´ ez-Ga ido* Ins i u o de Ciencias de Ma e iales de Se illa and Depa amen o de Fı ´sica de la Ma e ia Condensada, CSIC-Uni e sidad de Se illa, Apa ado 1065, 41080 Se illa, Spain Co espondence e-mail: [email p o ec ed] Key indica o s Single-c ys al X- ay s udy T= 293 K Mean (C–C) = 0.009 A ˚ R ac o = 0.046 wR ac o = 0.166 Da a- o-pa ame e a io = 8.8 Fo de ails o how hese key indica o s we e au oma ically de i ed om he a icle, see h p://jou nals.iuc .o g/e. Recei ed 23 May 2006 Accep ed 6 June 2006 #2006 In e na ional Union o C ys allog aphy All igh s ese ed In he i le compound, C 21 H 26 N 2 O 8 , he con igu a ions o he h ee chi al cen es a e known om he syn hesis, co e- sponding o a d-a abino con igu a ion. Bo h double bonds show he Econ igu a ion in he solid s a e. Packing o he molecules is go e ned by no mal an de Waals con ac s. Commen Following cu en wo k on asymme ic syn hesis om ca bo- hyd a es, A alos e al. (1995) de eloped a gene al syn hesis o suga 1,2-diaza-1,3-bu adienes. The i le compound, (I), was p epa ed by ea men o d-mannose wi h a yl hyd azines, and he co esponding a yl hyd azones we e eadily ob ained. Fu he con en ional ace yla ion and he mal 1,4-elimina ion ga e 1-a yl-1,2-diaza-1,3-bu adienes. In all cases, a yl diaza- bu adienes we e colou ed c ys alline compounds and could be s o ed o long pe iods wi hou app eciable decomposi ion. An X- ay in es iga ion o compound (I) was ca ied ou in o de o elucida e unequi ocally he molecula con o ma ion o (I) in he solid s a e. A pe spec i e iew o (I) wi h he a om-numbe ing scheme is shown in Fig. 1. P inicpal geome ic pa ame e s a e gi en in Table 1. Bo h double bonds exis in he Econ igu a ion in he solid s a e. The a abino chain (C4/C41/C42/C43) is plana , wi h he e minal a om C44 ha ing a maximum de ia ion om he leas -squa es plane o 0.017 (5) A ˚. The con igu a ions o he chi al cen es C41, C42 and C43 a e R,Sand R, espec i ely. The packing o he molecules is go e ned by no mal an de Waals con ac s. Expe imen al The i le compound was syn hesized om d-mannose (4-me hyl- phenyl) hyd azone, acco ding o he p ocedu e o A alos e al. (1995). Compound (I) was ec ys allized om e hanol–wa e . C ys al da a C 21 H 26 N 2 O 8 M = 434.44 O ho hombic, P212121 a= 14.065 (1) A ˚ b= 30.189 (2) A ˚ c= 5.6414 (3) A ˚ V= 2395.4 (3) A ˚ 3 Z=4 D x = 1.205 Mg m 3 Mo K adia ion = 0.09 mm 1 T= 293 (2) K P ism, ligh b own 0.32 0.28 0.16 mm Da a collec ion En a –Nonius CAD-4 di ac ome e !/2scans Abso p ion co ec ion: none 5210 measu ed e lec ions 2458 independen e lec ions 1196 e lec ions wi h I>2(I) R in = 0.027  max =25  3 s anda d e lec ions equency: 60 min in ensi y decay: 6% Re inemen Re inemen on F 2 R[F 2 >2(F 2 )] = 0.046 wR(F 2 ) = 0.166 S= 0.97 2458 e lec ions 280 pa ame e s . w= 1/[ 2 (F o2 ) + (0.0855P) 2 + 0.3134P] whe e P=(F o 2 +2F c 2 )/3 (/) max = 0.009  max = 0.22 e A ˚ 3  min =0.17 e A ˚ 3 Table 1 Selec ed geome ic pa ame e s (A ˚,). N2—N1 1.254 (6) N2—C3 1.404 (7) N1—C11 1.427 (7) C41—C4 1.493 (7) C4—C3 1.318 (8) N1—N2—C3 112.2 (5) N2—N1—C11 113.1 (5) C3—C4—C41 123.8 (5) C4—C3—N2 119.3 (5) H a oms we e e ined using a iding model, wi h C—H dis ances in he ange 0.93–0.98 A ˚and wi h U iso (H)=1.2U eq (C) o 1.5U eq (C me hyl ). In he absence o signi ican anomalous sca e e s, F iedel pai s we e me ged. The absolu e con igu a ion was assigned by e e ence o he known chi ali y o he s a ing ma e ial used in he syn hesis. Da a collec ion: CAD-4 EXPRESS (En a –Nonius, 1994); cell e inemen : CAD-4 EXPRESS; da a educ ion: XCAD4 (Ha ms & Wocadlo, 1995); p og am(s) used o sol e s uc u e: SIR2002 (Bu la e al., 2003); p og am(s) used o e ine s uc u e: SHELXL97 (Shel- d ick, 1997); molecula g aphics: ORTEPII (Johnson, 1976); so wa e used o p epa e ma e ial o publica ion: SHELXL97 and PARST (Na delli, 1995). The au ho s hank D Palacios, Uni e sidad de Ex ema- du a, Badajoz, Spain, o supplying he c ys al, and he Jun a de Andalucı ´a o inancial suppo . Re e ences A alos, M., Babiano, R., Cin as, P., Jimenez, J. L., Palacios, J. C. & Sanchez, J. B. (1995). Te ahed on Asymme y,6, 954–956. Bu la, M. C., Camalli, M., Ca ozzini, B., Casca ano, G. L., Giaco azzo, C., Polido i, G. & Spagna, R. (2003). J. Appl. C ys . 36, 1103. En a –Nonius (1994). CAD-4 EXPRESS. Ve sion 5.1/1.2. En a –Nonius, Del , The Ne he lands. Ha ms, K. & Wocadlo, S. (1995). XCAD4. Uni e si y o Ma bu g, Ge many. Johnson, C. K. (1976). ORTEPII. Repo ORNL-5138. Oak Ridge Na ional Labo a o y, Tennessee, USA. Na delli, M. (1995). J. Appl. C ys . 28, 659. Sheld ick, G. M. (1997). SHELXL97. Release 97-2. Uni e si y o Go ¨ ingen, Ge many. o ganic pape s o2812 Dia ´nez e al. C 21 H 26 N 2 O 8 Ac a C ys . (2006). E62, o2811–o2812 Figu e 1 A iew o he molecula s uc u e o (I), showing he a omic numbe ing scheme. Displacemen ellipsoids a e d awn a he 30% p obabili y le el. Fo cla i y, only he mos impo an H a oms a e shown.