Dimethyl 1,4-dihydro-4-(4-methoxy­phen­yl)-2,6-dimethyl­pyridine-3,5-dicarboxyl­ate

Loh, W.-S.; Fun, H.-K.; Reddy, B.P.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536810004940

Volume 66
Part 3
Pages o587-o588
March 2010

Received 29 January 2010
Accepted 8 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 20.6
Details

Dimethyl 1,4-dihydro-4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate

Wan-Sin Loh,^a ⁺ Hoong-Kun Fun,^a ^*⁺⁺ B. Palakshi Reddy,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₈H₂₁NO₅, the dihydropyridine ring adopts a flattened-boat conformation and its planar part forms a dihedral angle of 84.60 (2)° with the benzene ring. In the crystal, intermolecular N-HO and C-HO hydrogen bonds result in the formation of zigzag layers parallel to (001). These layers are interconnected via C-H [pi] interactions.

Related literature

For the synthesis, see: Rathore et al. (2009). For general background and applications of 1,4-dihydropyridine derivatives, see: Bocker & Guengerich (1986); Cooper et al. (1992); Gaudio et al. (1994); Gordeev et al. (1996); Sunkel et al. (1992); Vo et al. (1995). For ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Fun et al. (2009a,b). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₈H₂₁NO₅
M_r = 331.36
Triclinic, $[P \overline 1]$
a = 7.4106 (3) Å
b = 9.5715 (5) Å
c = 11.7771 (6) Å
= 83.029 (1)°
= 83.834 (1)°
= 77.424 (1)°
V = 806.46 (7) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.35 × 0.34 × 0.24 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.966, T_max = 0.976
19600 measured reflections
4664 independent reflections
4319 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.110
S = 1.05
4664 reflections
226 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.48 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1N1O4ⁱ	0.87 (2)	2.23 (2)	3.0906 (10)	169 (1)
C14-H14AO1ⁱⁱ	0.96	2.54	3.4631 (13)	162
C18-H18BO4ⁱ	0.96	2.56	3.4558 (12)	156
C12-H12BCg1ⁱⁱⁱ	0.96	2.79	3.6549 (11)	151
Symmetry codes: (i) x+1, y, z; (ii) x+1, y-1, z; (iii) -x+1, -y+1, -z.

Data collection: APEX DUO (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5029 ).

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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. 28, 1596-1603.
Bruker (2009). APEX DUO, 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.
Fun, H.-K., Goh, J. H., Reddy, B. P., Sarveswari, S. & Vijayakumar, V. (2009a). Acta Cryst. E65, o2247-o2248.
Fun, H.-K., Quah, C. K., Reddy, B. P., Sarveswari, S. & Vijayakumar, V. (2009b). Acta Cryst. E65, o2255-o2256.
Gaudio, A. C., Korolkovas, A. & Takahata, Y. (1994). J. Pharm. Sci. 83, 1110-1115.
Gordeev, M. F., Patel, D. V. & Gordon, E. M. (1996). J. Org. Chem. 61, 924-928.
Rathore, R. S., Reddy, B. P., Vijayakumar, V., Ragavan, R. V. & Narasimhamurthy, T. (2009). Acta Cryst. B65, 375-381.
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., Villarroya, M., González-Morales, M. A., López, M. G., Cillero, J., Alonso, S. & Priego, J. G. (1992). J. Med. Chem. 35, 2407-2414.
Vo, D., Matowe, W. C., Ramesh, M., Iqbal, N., Wolowyk, M. W., Howlett, S. E. & Knaus, E. E. (1995). J. Med. Chem. 38, 2851-2859.

organic compounds