electronic reprintActa Crystallographica Section E

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Diethyl 4-(4-ethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Hoong-Kun Fun, Jia Hao Goh, B. Palakshi Reddy, S. Sarveswari and V.Vijayakumar

Acta Cryst. (2009). E65, o2247–o2248

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Acta Cryst. (2009). E65, o2247–o2248 Fun et al. · C21H27NO5

Diethyl 4-(4-ethoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Hoong-Kun Fun,a*‡ Jia Hao Goh,a B. Palakshi Reddy,b

S. Sarveswarib and V. Vijayakumarb

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800

USM, Penang, Malaysia, and bOrganic Chemistry Division, School of Science and

Humanities, VIT University, Vellore 632 014, India

Correspondence e-mail: hkfun@usm.my

Received 18 August 2009; accepted 21 August 2009

Key indicators: single-crystal X-ray study; T = 296 K; mean �(C–C) = 0.002 A;

R factor = 0.055; wR factor = 0.161; data-to-parameter ratio = 20.9.

In the title compound, C21H27NO5, the dihydropyridine ring

adopts a boat conformation. The ethoxyphenyl ring is oriented

approximately perpendicular to the planar part of the

dihydropyridine ring, making a dihedral angle of 89.45 (6)�.An intramolecular C—H� � �O hydrogen bond generates an

S(6) ring motif. In the crystal structure, neighbouring

molecules are linked into chains along the a axis by N—

H� � �O hydrogen bonds and the chains are interconnected into

two-dimensional networks parallel to the ab plane by C—

H� � �O hydrogen bonds. The structure is further stabilized by

weak C—H� � �� interactions.

Related literature

For general background to and applications of 1,4-dihydro-

pyridine derivatives, see: Bocker & Guengerich (1986);

Cooper et al. (1992); Vo et al. (1995); Gaudio et al. (1994);

Gordeev et al. (1996); Sunkel et al. (1992). For ring confor-

mations and ring puckering analysis, see: Boeyens (1978);

Cremer & Pople (1975). For hydrogen-bond motifs, see:

Bernstein et al. (1995). For bond-length data, see: Allen et al.

(1987). For a related structure, see: Thenmozhi et al. (2009).

For the stability of the temperature controller used for the

data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C21H27NO5

Mr = 373.44Triclinic, P1a = 7.5557 (1) Ab = 9.5697 (1) Ac = 14.0553 (2) A� = 85.844 (1)�

� = 87.679 (1)�

� = 81.458 (1)�

V = 1001.91 (2) A3

Z = 2Mo K� radiation� = 0.09 mm�1

T = 296 K0.28 � 0.27 � 0.07 mm

Data collection

Bruker SMART APEXII CCDarea-detector diffractometer

Absorption correction: multi-scan(SADABS; Bruker, 2005)Tmin = 0.976, Tmax = 0.994

20664 measured reflections5290 independent reflections3602 reflections with I > 2�(I)Rint = 0.027

Refinement

R[F 2 > 2�(F 2)] = 0.055wR(F 2) = 0.161S = 1.025290 reflections253 parameters

H atoms treated by a mixture ofindependent and constrainedrefinement

��max = 0.32 e A�3

��min = �0.24 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N1—H1N1� � �O2i 0.85 (2) 2.18 (2) 3.0045 (19) 165 (2)C12—H12A� � �O4ii 0.97 2.51 3.458 (2) 166C20—H20A� � �O3 0.96 2.14 2.7774 (19) 122C16—H16A� � �Cg1iii 0.96 2.83 3.767 (2) 165

Symmetry codes: (i) x � 1; y; z; (ii) x; y þ 1; z; (iii) �x þ 2;�y þ 1;�z þ 2. Cg1 is thecentroid of the C1–C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT

(Bruker, 2005); data reduction: SAINT; program(s) used to solve

structure: SHELXTL (Sheldrick, 2008); program(s) used to refine

structure: SHELXTL; molecular graphics: SHELXTL; software used

to prepare material for publication: SHELXTL and PLATON (Spek,

2009).

HKF and JHG thank Universiti Sains Malaysia (USM) for

the Research University Golden Goose grant (No. 1001/

PFIZIK/811012). JHG also thanks USM for the award of a

USM fellowship. VV is grateful to DST–India for funding

through the Young Scientist Scheme (Fast Track Proposal).

organic compounds

Acta Cryst. (2009). E65, o2247–o2248 doi:10.1107/S160053680903339X Fun et al. o2247

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

‡ Thomson Reuters ResearcherID: A-3561-2009.

electronic reprint

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: CI2893).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555–1573.

Bocker, R. H. & Guengerich, F. P. (1986). J. Med. Chem. 29, 1596–1603.Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320.Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.

Cooper, K., Fray, M. J., Parry, M. J., Richardson, K. & Steele, J. (1992). J. Med.Chem. 35, 3115–3129.

Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.Gaudio, A. C., Korolkovas, A. & Takahata, Y. (1994). J. Pharm. Sci. 84, 1110–

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928.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Sunkel, C. E., de Casa-Juana, M. F., Santos, L., Garcia, A. G., Artalejo, C. R.,

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Thenmozhi, M., Kavitha, T., Satyanarayana, V. S. V., Vijayakumar, V. &Ponnuswamy, M. N. (2009). Acta Cryst. E65, o1921–o1922.

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organic compounds

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