In the title compound, Csb 27Hsb 22Clsb 3Nsb 3Osb 2, the dihydro-pyridine ring has a boat conformation. The mol-ecules are linked by N-H⋅sO, N-H⋅sCl, C-H⋅sN and C-H⋅sO hydrogen bonds

Anamik, S.

Dinesh, M.

Doreswamy, B. H.

Kinnari, D.

Mahendra, M

Shashidhara Prasad, J.

Sridhar, M. A.

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organic papersActa Cryst. (2005). E61, o2567–o2569 doi:10.1107/S1600536805022038 Mahendra et al.  C27H22Cl3N3O2 o2567Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368N,N0-Bis(2-chlorophenyl)-4-(4-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamideM Mahendra,aB. H. Doreswamy,aM. A. Sridhar,aJ. Shashidhara Prasad,a*D. Kinnari,b M. Dineshb andS. AnamikbaDepartment of Studies in Physics,Mansagangotri, University of Mysore, Mysore570 006, India, and bDepartment of Chemistry,Saurashtra University, Rajkot 360 005, IndiaCorrespondence e-mail:mas@physics.uni-mysore.ac.inKey indicatorsSingle-crystal X-ray studyT = 295 KMean (C–C) = 0.005 A˚R factor = 0.051wR factor = 0.181Data-to-parameter ratio = 14.0For details of how these key indicators wereautomatically derived from the article, seehttp://journals.iucr.org/e.# 2005 International Union of CrystallographyPrinted in Great Britain – all rights reservedIn the title compound, C27H22Cl3N3O2, the dihydropyridinering has a boat conformation. The molecules are linked by N—H  O, N—H  Cl, C—H  N and C—H  O hydrogenbonds.Comment1,4-Dihydropyridines are known for their pronounced drugactivity, such as calcium channel antagonists (Janis & Triggle,1983) and antihypertensive agents (Fossheim et al., 1982).Recently, symmetrical 1,4-dihydropyridines (1,4-DHP) having3,5-dicarbamoyl substituents (Desai et al., 2001) opened up afresh approach to the synthesis of new molecules having betterpharmacokinetic properties (Triggle, 2003). Our group hassynthesized and studied antitubercular activity by applyingtwo- and three-dimensional quantitative structure–activityrelationships (QSAR) to a series of 3,5-dicarbamoyl func-tionalities in 1,4-dihydropyridine (Desai et al., 2001; Kharkaret al., 2002). It was assumed that the presence of a group suchas Cl or CH3 at position 2 of the substituted phenylcarbamoylgroup decreased the solvent-accessible surface area aroundthe amide bond and hence decreased the antitubercularactivity. However, when an electron-withdrawing group ispresent at position 2 of the phenylcarbamoyl group it results inhigher activity (Kharkar et al., 2002). Against this background,the title compound, (I) (Fig. 1), was synthesized and its crystalstructure is reported here.Most of the bond lengths and angles have normal valuesand are comparable with those reported for similar structures(Sagar et al., 1999; Mahendra et al., 2004). The 1,4-DHP ringhas a boat conformation, with atoms N1 and C4 displaced by0.126 (3) and 0.271 (3) A˚, respectively, from the mean planeReceived 30 June 2005Accepted 8 July 2005Online 16 July 2005through the other four C atoms. The other structural char-acteristics are the conformations of the 2-chlorophenyl-carbamoyl groups on the dihydropyridine ring. Each carbonylgroup of 2-chlorophenylcarbamoyl can be oriented in asynperiplanar (cis) or antiperiplanar (trans) conformationwith respect to the adjacent C C double bond of thedihdropyridine ring. The observed torsion angles are C2—C3—C9—O10 [168.5 (3)] and C6—C5—C19—O20[28.8 (5)], indicating trans and cis conformations, respectively.The structure exhibits both intra- and intermolecularhydrogen bonds (Table 2 and Fig. 2), which help to stabilizethe crystal structure. The intermolecular hydrogen bondsN1—H1  O20i and C34—H34  O10ii (symmetry codes as inTable 2) link the molecules into infinite one-dimensionalchains (Fig. 2).ExperimentalA mixture of 2-chloroacetoacetanilide (4.22 g, 0.02 mol) and4-chlorobenzaldehyde (1.40 g, 0.01 mol) was heated continuously atreflux for 15 min, with stirring, using 30 ml methanol as solvent.Ammonia (4 ml) was added to the reaction mixture after 3 h. A light-yellow product separated in the flask; this was filtered off, washedtwice with methanol and finally dried in a hot-air oven. Recrystalli-zation from dimethylformamide gave a yield of 53–54% (m.p. 472 K).Analysis calculated: C 64.37, H 4.82, Cl13.57, N 8.04, O 9.19%. 3 g wastaken up in 30 ml of methanol/dimethylformamide (8:2). Charcoal(3 g) was added and the solution heated for 5 min. It was then filteredwhile hot through a Whatman 42 filter paper. The solution was keptfor 30 d in a conical flask with the stopper left slightly open, and pale-yellow crystals grew by evaporation.Crystal dataC27H22Cl3N3O2Mr = 526.83Monoclinic, C2=ca = 20.566 (2) A˚b = 10.698 (1) A˚c = 22.789 (2) A˚ = 104.300 (2)V = 4858.6 (6) A˚3Z = 8Dx = 1.440 Mg m3Mo K radiationCell parameters from 8244reflections = 2.2–27.9 = 0.41 mm1T = 295 (2) KBlock, pale yellow0.25  0.2  0.2 mmData collectionMacScience DIPLabo 32001diffractometer! scansAbsorption correction: none8244 measured reflections4452 independent reflections3458 reflections with I > 2(I)Rint = 0.017max = 27.9h = 23 ! 24k = 10 ! 11l = 29 ! 29RefinementRefinement on F 2R[F 2 > 2(F 2)] = 0.051wR(F 2) = 0.181S = 1.064452 reflections318 parametersH-atom parameters constrainedw = 1/[2(Fo2) + (0.0987P)2+ 5.2071P]where P = (Fo2 + 2Fc2)/3(/)max = 0.001max = 0.57 e A˚3min = 0.54 e A˚3Table 1Selected geometric parameters (A˚, ).Cl18—C17 1.740 (3)Cl28—C27 1.735 (4)Cl33—C32 1.739 (3)O10—C9 1.213 (4)O20—C19 1.227 (3)N1—C2 1.382 (4)N1—C6 1.376 (4)N11—C9 1.357 (4)N11—C12 1.404 (4)N21—C19 1.353 (4)N21—C22 1.410 (5)C2—N1—C6 124.0 (2)C9—N11—C12 129.0 (2)C19—N21—C22 128.8 (3)N1—C2—C3 119.1 (3)N1—C2—C8 112.0 (2)N1—C6—C5 119.5 (3)N1—C6—C7 112.9 (3)O10—C9—N11 120.8 (2)O10—C9—C3 120.2 (3)N11—C9—C3 119.1 (2)N11—C12—C17 118.3 (3)N11—C12—C13 124.2 (3)Cl18—C17—C12 120.0 (3)Cl18—C17—C16 118.1 (3)O20—C19—N21 120.7 (3)O20—C19—C5 123.5 (3)N21—C19—C5 115.8 (2)N21—C22—C23 124.0 (3)N21—C22—C27 118.5 (3)Cl28—C27—C22 119.8 (3)Cl28—C27—C26 118.1 (3)Cl33—C32—C31 119.8 (2)Cl33—C32—C34 119.5 (2)organic paperso2568 Mahendra et al.  C27H22Cl3N3O2 Acta Cryst. (2005). E61, o2567–o2569Figure 1View of (I), shown with 50% probability displacement ellipsoids.Figure 2The crystal packing in (I), viewed down the b axis. Dashed lines indicatehydrogen bonds.Table 2Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN1—H1  O20i 0.86 2.05 2.891 (3) 167N11—H11  Cl18 0.86 2.46 2.943 (3) 116N21—H21  Cl28 0.86 2.48 2.935 (3) 114C4—H4  N21 0.98 2.54 2.905 (4) 102C7—H7C  O20 0.96 2.36 2.838 (4) 110C8—H8B  O20i 0.96 2.56 3.423 (4) 149C13—H13  O10 0.93 2.24 2.833 (5) 121C23—H23  O20 0.93 2.28 2.842 (5) 119C34—H34  O10ii 0.93 2.49 3.227 (4) 136Symmetry codes: (i) xþ 12;þy  12;z 12; (ii) xþ 12;y þ 52;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˚ andN—H = 0.86 A˚; Uiso(H) values were set equal to xUeq(carrier atom),where x = 1.5 for methyl H atoms and 1.2 for all other H atoms.Data collection: XPRESS (MacScience, 2002); cell refinement:SCALEPACK (Otwinowski & Minor, 1997); data reduction:SCALEPACK and DENZO (Otwinowski & Minor, 1997);program(s) used to solve structure: SHELXS97 (Sheldrick, 1990);program(s) used to refine structure: SHELXL97 (Sheldrick, 1997);molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson,1976); software used to prepare material for publication:SHELXL97.We thank the DST, Government of India, for financialassistance (project SP/I2/FOO/93). MM thanks the CSIR,Government of India, for the award of a Senior ResearchFellowship.ReferencesDesai, B., Sureja, D., Naliapara, Y., Saxena, A. K. & Shah, A. (2001). Biorg.Med. Chem. 9, 1993–1998.Fossheim, R., Svarteng, K., Mostad, A., Rømming, C., Shelter, E. & Triggle,D. J. (1982). J. Med. Chem. 25, 126–131.Janis, R. A. & Triggle, D. J. (1983). J. Med. Chem. 26, 775–785.Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge NationalLaboratory, Tennessee, USA.Kharkar, P. S., Desai, B., Gaveriya, H., Naliapara, Y., Loriya, R. M., Varu, B.,Shah, A. & Kulkarni, V. M. (2002). J. Med. Chem. 45, 4858–4867.MacScience (2002). XPRESS. MacScience Co. Ltd, Yokohama, Japan.Mahendra, M., Doreswamy, B. H., Dinesh, M., Gautam, P., Yogesh, N.,Kinnari, D., Anamik, S., Sridhar M. A. & Shashidhara, J. S. (2004). J. Chem.Res. 12, 843–844.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. New York: Academic Press.Sagar, M. B., Ravikumar, K., Mehdi, S., Sadamandam, Y. S., Giju, K. T. &Jemmis, E. D. (1999). J. Chem. Crystallogr. 29, 481–491.Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.Sheldrick, G. M. (1997). SHELXL97. University of Go¨ttingen, Germany.Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.Triggle D. J. (2003). Mini Rev. Med. Chem. 3, 215–223 .organic papersActa Cryst. (2005). E61, o2567–o2569 Mahendra et al.  C27H22Cl3N3O2 o2569

N,N'Bis(2-chloro-phen-yl)-4-(4-chloro-phen-yl)-2,6-dimeth-yl-1,4-dihydro-pyridine-3,5-dicarboxamide

http://eprints.uni-mysore.ac.in/7624/1/N%2CN000-Bis%282-chlorophenyl%29-4-%284-chlorophenyl%29-2%2C6.pdf

N,N'Bis(2-chloro-phen-yl)-4-(4-chloro-phen-yl)-2,6-dimeth-yl-1,4-dihydro-pyridine-3,5-dicarboxamide

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