Methyl 4-(4-chloro­phen­yl)-8-iodo-2-methyl-6-oxo-1,6-dihydro-4H-pyrimido[2,1-b]quinazoline-3-carboxyl­ate

Nayak, S.K.; Venugopala, K.N.; Odhav, B.

doi:10.1107/S1600536812050787

Volume 69
Part 1
Pages o123-o124
January 2013

Received 25 November 2012
Accepted 13 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.024
wR = 0.059
Data-to-parameter ratio = 14.1
Details

Methyl 4-(4-chlorophenyl)-8-iodo-2-methyl-6-oxo-1,6-dihydro-4H-pyrimido[2,1-b]quinazoline-3-carboxylate

Susanta K. Nayak,^a ^* K. N. Venugopala ^b ^* and Bharti Odhav ^b

^aCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy, and ^bDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa
Correspondence e-mail: nksusa@gmail.com, katharigattav@dut.ac.za

In the title compound, C₂₀H₁₅ClIN₃O₃, the dihedral angle between the quinazolinone ring system [r.m.s. deviation = 0.047 (2) Å] and the pendant benzene ring is 82.63 (11)°. The molecular conformation is stabilized by intramolecular C-HO interactions. In the crystal, the molecules are linked by N-HO hydrogen bonds into chains along the a-axis direction. Another set of chains propagating along [101] is formed due to intermolecular ICl short contacts of 3.427 (1) Å, thus giving layers parallel to (010). The layers are connected by C-H [pi] and [pi] - [pi] interactions, the shortest distance between the centroids of aromatic rings being 3.8143 (16) Å.

Related literature

For crystal structures of dihydropyrimidines, see: Nayak et al. (2010, 2011a,b,c); Venugopala et al. (2012). For applications of dihydropyrimidines, see: Kappe (2000). For halogen-involving interactions, see: Nayak et al. (2011b).

Experimental

Crystal data

C₂₀H₁₅ClIN₃O₃
M_r = 507.70
Triclinic, $[P \overline 1]$
a = 7.3443 (15) Å
b = 10.847 (2) Å
c = 12.475 (3) Å
= 106.66 (3)°
= 103.53 (2)°
= 92.79 (3)°
V = 918.5 (4) Å³
Z = 2
Mo K radiation
= 1.92 mm^-1
T = 173 K
0.25 × 0.14 × 0.12 mm

Data collection

Bruker APEXII Kappa DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.646, T_max = 0.803
7109 measured reflections
3602 independent reflections
3147 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.059
S = 1.09
3602 reflections
255 parameters
H-atom parameters constrained
_max = 0.89 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	0.88	2.04	2.903 (3)	167
C5-H5AO1	0.98	2.22	2.807 (4)	117
C8-H8O2	0.95	2.49	3.167 (4)	128
C1-H1BCg1ⁱⁱ	0.98	2.67	3.647 (4)	175
Symmetry codes: (i) x-1, y, z; (ii) -x-1, -y-1, -z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2082 ).

Acknowledgements

The authors thank Durban University of Technology for facilities. KNV thanks the NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship.

References

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Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.
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Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011b). Cryst. Growth Des. 11, 1578-1596.
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Nayak, S. K., Venugopala, K. N., Chopra, D., Vasu & Guru Row, T. N. (2010). CrystEngComm, 12, 1205-1216.
Nayak, S. K., Venugopala, K. N., Govender, T., Kruger, H. G., Maguire, G. E. M. & Row, T. N. G. (2011c). Acta Cryst. E67, o3069-o3070.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Venugopala, K. N., Nayak, S. K. & Odhav, B. (2012). Acta Cryst. E68, o2977-o2978.

organic compounds