In the crystal structure of the title compound, C\sb 24H\sb 22BrClN\sb 4O\sb 3, there are C—-H⋅sO and C—-H⋅sBr intermolecular hydrogen bonds, and also C—-H⋅sO, C—-H⋅sBr and C—-H⋅sN intramolecular hydrogen bonds

Rangappa, K. S.

Sarala, G.

Shashidhara Prasad, J.

Sridhar, M. A.

Thimmegowda, N. R.

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organic paperso5110 Sarala et al.  C24H22BrClN4O3 doi:10.1107/S1600536806041079 Acta Cryst. (2006). E62, o5110–o5111Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-536810-(2-Bromo-4,5-dimethoxybenzyl)-7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraazadibenzo[a,d]cyclohepten-11-oneG. Sarala,a N. R. ThimmeGowda,b K. S. Rangappa,bM. A. Sridhara* andJ. Shashidhara PrasadaaDepartment of Studies in Physics,Manasagangotri, University of Mysore, Mysore570 006, India, and bDepartment of Studies inChemistry, Manasagangotri, University ofMysore, Mysore 570 006, IndiaCorrespondence e-mail:mas@physics.uni-mysore.ac.inKey indicatorsSingle-crystal X-ray studyT = 295 KMean (C–C) = 0.006 A˚R factor = 0.050wR factor = 0.155Data-to-parameter ratio = 13.4For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.Received 30 August 2006Accepted 5 October 2006# 2006 International Union of CrystallographyAll rights reservedIn the crystal structure of the title compound, C24H22BrCl-N4O3, there are C—H  O and C—H  Br intermolecularhydrogen bonds, and also C—H  O, C—H  Br and C—H  N intramolecular hydrogen bonds.CommentThere has been widespread interest in the chemistry ofazepines due to their biological activities and their applica-tions as anti-HIV drugs (Dyatkin et al., 1998). This is the firsthuman immuno-deficiency virus type 1 (HIV-1) non-nucleo-side reverse transcriptase (RT) inhibitor to obtain regulatoryapproval (Cywin et al., 1998). It prevents the damage to theimmune system and reduces the risk of developing AIDS-related illness (Campiani et al., 1999). The compound 7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one is an intermediate of a potentanti-HIV drug, Nevirapine. The N-alkylation of thecompound by different alkyl and aryl halides leads to novelmolecules of biological interest.In the title compound (I), C24H22BrClN4O3, the centralseven-membered ring is puckered. Atoms N5 and N13 deviatefrom the plane defined by the atoms N3/C2/C16–C8/N7/C6–C4 by 1.091 (3) and 0.952 (3) A˚, respectively. This deviationmay be attributed to the substitution of the 5-cyclopropyl and10-(2-bromo-4,5-dimethoxybenzyl) groups. The total puck-ering amplitude QT (Cremer & Pople, 1975) is 2.606 (4) A˚.The structure exhibits intermolecular hydrogen bonding ofthe types C—H  O and C—H  Br (Table 1 and Fig. 2). Thepacking of the molecules, when viewed down the a axis (Fig. 2),indicates that the molecules are interlinked by hydrogenbonds.ExperimentalTo a solution of 7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraazadibenzo[a,d]cyclohepten-11-one (0.5 g, 1.66 mmol)in 5 ml of DMF, a mixture of 1-bromo-2-bromomethyl-4,5-dimeth-oxybenzene (0.51 g, 1.66 mmol) and anhydrous powdered potassiumcarbonate (0.688 g, 4.98 mmol) were added, and the mixture washeated to 333 K for 6 h. The reaction was monitored by TLC. Aftercompletion of the reaction, the solvent was removed under reducedpressure and the product extracted with ethyl acetate. The organiclayer was dried with anhydrous sodium sulfate. The solvent wasevaporated to obtain the crude product which was purified over silicagel using hexane and ethyl acetate (8:2) as an eluent for columnchromatography (yield: 80%). The pure product thus obtained wasrecrystallized by slow evaporation of an acetonitrile solution. Afterfive days, pale-yellow crystals were obtained. Melting point: 461–463 K. Elemental analysis data in (%) for C24H22BrClN4O3, calcu-lated: C 54.41, H 4.19, N 10.57; found: C 54.43, H 4.17, N 10.54.Crystal dataC24H22BrClN4O3Mr = 529.82Monoclinic, P21=ca = 9.0680 (9) A˚b = 16.7840 (9) A˚c = 16.1960 (16) A˚ = 107.260 (2)V = 2354.0 (4) A˚3Z = 4Dx = 1.495 Mg m3Mo K radiation = 1.89 mm1T = 295 (2) KBlock, pale yellow0.30  0.25  0.25 mmData collectionMacScience DIPLabo 32001diffractometer! scansAbsorption correction: none7627 measured reflections4048 independent reflections2933 reflections with I > 2(I)Rint = 0.032max = 25.0RefinementRefinement on F 2R[F 2 > 2(F 2)] = 0.050wR(F 2) = 0.155S = 1.054048 reflections301 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.0944P)2+ 0.2553P]where P = (Fo2 + 2Fc2)/3(/)max < 0.001max = 0.40 e A˚3min = 0.68 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC21—H13B  Br29i 0.97 2.72 3.514 (5) 139C22—H22A  O18 0.97 2.33 2.730 (6) 104C22—H22B  Br29 0.97 2.71 3.239 (5) 115C27—H27  O18ii 0.93 2.47 3.390 (6) 170C17—H33B  N13 0.96 2.56 2.961 (5) 105Symmetry codes: (i) xþ 1; y 12;zþ 12; (ii) xþ 1; y; z.H atoms were placed at idealized positions and allowed to ride ontheir parent atoms with C—H distances in the range 0.93–0.98 A˚;Uiso(H) = 1.2Ueq(carrier atom) for all H atoms.Data collection: XPRESS (MacScience, 2002); cell refinement:SCALEPACK (Otwinowski & Minor, 1997); data reduction:DENZO and SCALEPACK (Otwinowski and Minor, 1997);program(s) used to solve structure: SHELXS97 (Sheldrick, 1997);program(s) used to refine structure: SHELXL97 (Sheldrick, 1997);molecular graphics: PLATON (Spek, 2003); ORTEPII (Johnson,1976); software used to prepare material for publication: PLATON.The authors are thankful to the Department of Science andTechnology, New Delhi, for financial support under the projectSP/I2/FOO/93, UGC-SAP (Phase-1) No. F.540/10/DRS/2004(SAP-I) and the DST–FIST programme is gratefullyacknowledged.ReferencesCampiani, G., Morelli, E., Fabbrini, M., Nacci, V., Greco, G., Novellino, E.,Ramunno, A., Maga, G., Spadari, S., Caliendo, G., Bergamini, A., Faggioli,E., Uccella, I., Bolacchi, F., Marini, S., Coletta, M., Nacca, A. & Caccia, S.(1999). J. Med. Chem. 42, 4462–4470.Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.Cywin, C. L., Klunder, J. M., Hoermann, M., Brickwood, J. R., David, E., Grob,P. M., Schwartz, R., Pauletti, D., Barringer, K. J., Shih, C.-K., Sorge, C. L.,Erickson, D. A., Joseph, D. P. & Hattox, S. E. (1998). J. Med. Chem. 41,2972–2984.Dyatkin, A. B., Brickwood, J. R. & Proudfoot, J. R. A. (1998). Bioorg. Med.Chem. Lett. 8, 2169–2172.Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge NationalLaboratory, Tennessee, USA.MacScience (2002). XPRESS. MacScience Co. Ltd, Yokohama, Japan.Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.Sweet, pp. 307–326. London: Academic Press.Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University ofGo¨ttingen, Germany.Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.organic papersActa Cryst. (2006). E62, o5110–o5111 Sarala et al.  C24H22BrClN4O3 o5111Figure 1The molecular structure of (I), with 50% probability displacementellipsoids.

10-(2-bromo-4,5-dimethoxybenzyl)-7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraazadibenzo[a,d]cyclohepten-11-one

http://eprints.uni-mysore.ac.in/6262/1/10-%282-bromo-4%2C5-dimethoxybenzyl%29.pdf

10-(2-bromo-4,5-dimethoxybenzyl)-7-chloro-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraazadibenzo[a,d]cyclohepten-11-one

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