Synthesis and X-ray diffraction data of 6,8-dimethyl-cis-2-vinyl-2,3,4,5- tetrahydro-1H-benzo[b]azepin-4-ol and 8-chloro-9-methyl-cis-2- (prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol M. A. Macı ´as and J. A. Henao a) Grupo de Investigacio ´n en Quı ´mica Estructural (GIQUE), Escuela de Quı ´mica, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia Lina Marı ´a Acosta and Alirio Palma Laboratorio de Sı ´ntesis Orga ´nica (LSO), Centro de Investigacio ´n en Biomole ´culas, (CIBIMOL), Escuela de Quı ´mica, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia (Received 2 May 2011; accepted 14 May 2011) The 6,8-dimethyl-cis-2-vinyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (2a) (Chemical formula C 14 H 19 NO) and 8-chloro-9-methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4- ol (2b) (Chemical formula C 14 H 18 ClNO) were prepared via the reductive cleavage of the bridged N- O bond of the corresponding 1,4-epoxytetrahydro-1-benzazepines. The X-ray powder diffraction patterns for the new compounds were obtained. The compound 2a was found to crystallize in an orthorhombic system with space group Pmn2 1 (No. 31), refined unit-cell parameters a ¼ 19.422(6) A ˚ , b ¼ 6.512(3) A ˚ , c ¼ 9.757(4) A ˚ and V ¼ 1234.0(5) A ˚ 3 . The compound 2b was found to crystallize in a monoclinic system with space group P2 1 =m (No. 11), refined unit-cell parameters a ¼ 17.570(4) A ˚ , b ¼ 8.952(3) A ˚ , c ¼ 14.985(4) A ˚ , b ¼ 101.66(2)  , and V ¼ 2308.3(9) A ˚ 3 . V C 2011 International Centre for Diffraction Data. [DOI: 10.1154/1.3656975] Key words: tetrahydro-1-benzazepine, X-ray powder diffraction data, antiparasitic agents I. INTRODUCTION Tetrahydro-1-benzazepine derivatives exhibit a broad spectrum of diverse and important pharmacological proper- ties. For example, different tetrahydro-1-benzazepines have been reported as potent arginine vasopressin antagonists for both V 1A and V 2 receptors (Matthews et al., 2003; Shimada et al., 2000), and some other derivatives have been reported as potent inhibitors of cyclin dependent kinases (Schultz et al., 1999). Other tetrahydro-1-benzazepine derivatives such as paullones exhibited potent activity against parasites of Leishmania mexicana (Knockaert et al., 2002) and Trypa- nosoma cruzi (Zuccotto et al., 2001), the etiologic agents of the leishmaniasis and Chagas disease, respectively. This broad spectrum of biological activity awakened the interest of the synthetic chemists in this heterocyclic system. In this context, we have developed an efficient synthetic method to obtain new cis-2-aryl-4-hydroxytetrahydro-1-benzazepines starting from ortho-allyl-N-benzylanilines (Go ´mez et al., 2006). Compounds of this type showed promising activity against T. cruzi and Leishmania chagasi parasites (Palma et al., 2009, Go ´mez-Ayala et al., 2006, 2010). Additionally, we have also described the stereoselective synthesis of cis-4-hydroxy-2-alkenyltetrahydro-1-benzazepines (Acosta et al, 2010). In this work, we report the X-ray powder dif- fraction (XRPD) data of 6,8-dimethyl-cis-2-vinyl-2,3,4,5- tetrahydro-1H-benzo[b]azepin-4-ol (2a) and 8-chloro-9- methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo [b]azepin-4-ol (2b). II. EXPERIMENTAL A. Synthesis As shown in Figure 1, the synthesis of the compounds 2a and 2b involves the treatment of a methanolic cooled ice bath solution of the 1,4-epoxy-cycloadducts 1a and 1b with a seven-fold molar excess of glacial acetic acid, ten-fold molar excess of zinc powder, and seven-fold molar excess of hydrochloric acid (37% HCl). The organic crudes were purified by column chromatography on silica gel using hep- tane=ethyl acetate (compositions ranged from 10:1 to 1:1 v=v) as eluent to give 2a and 2b in 94% and 90% yields, respectively. B. Powder data collection A small portion of the title compounds were gently ground in an agate mortar and sieved to a grain size less than 38 lm. The specimens were mounted on a zero-background specimen holder (Buhrke et al., 1998). The XRPD patterns were recorded with a D8 FOCUS BRUKER diffractometer operating in Bragg-Brentano geometry equipped with an X-ray tube (Cu Ka radiation: k ¼ 1.5406 A ˚ , 40 kV and 40 mA) using a nickel filter and a one-dimensional LynxEye detector. A fixed antiscatter slit of 8 mm, receiving slit of 1 mm, soller slits of 2.5  , and a detector slit of 3 mm were used. The scan range was from 2  to 70  2h with a step size of 0.02  2h and a count time of 0.4 s=step. XRPD data were collected at room temperature (298 K). PowderX program (Dong, 1999) was used to remove the background (Sonneveld and Visser, 1975), smoothing (Saviztky and Golay, 1964), to eliminate the Ka 2 component a) Author to whom correspondence should be addressed. Electronic mail: jahenao@uis.edu.co 346 Powder Diffraction 26 (4), December 2011 0885-7156/2011/26(4)/346/4/$30.00 V C 2011 JCPDS-ICDD 346