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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 [sigma](C-C) = 0.004 Å
R = 0.024
wR = 0.059
Data-to-parameter ratio = 14.1
Details
Open access

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

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-H...O interactions. In the crystal, the molecules are linked by N-H...O hydrogen bonds into chains along the a-axis direction. Another set of chains propagating along [101] is formed due to intermolecular I...Cl 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[Nayak, S. K., Venugopala, K. N., Chopra, D., Vasu & Guru Row, T. N. (2010). CrystEngComm, 12, 1205-1216.], 2011a[Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011a). CrystEngComm, 13, 591-605.],b[Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011b). Cryst. Growth Des. 11, 1578-1596.],c[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.]); Venugopala et al. (2012[Venugopala, K. N., Nayak, S. K. & Odhav, B. (2012). Acta Cryst. E68, o2977-o2978.]). For applications of dihydropyrimidines, see: Kappe (2000[Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.]). For halogen-involving interactions, see: Nayak et al. (2011b[Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011b). Cryst. Growth Des. 11, 1578-1596.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15ClIN3O3

  • Mr = 507.70

  • Triclinic, [P \overline 1]

  • a = 7.3443 (15) Å

  • b = 10.847 (2) Å

  • c = 12.475 (3) Å

  • [alpha] = 106.66 (3)°

  • [beta] = 103.53 (2)°

  • [gamma] = 92.79 (3)°

  • V = 918.5 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.646, Tmax = 0.803

  • 7109 measured reflections

  • 3602 independent reflections

  • 3147 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.059

  • S = 1.09

  • 3602 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.88 2.04 2.903 (3) 167
C5-H5A...O1 0.98 2.22 2.807 (4) 117
C8-H8...O2 0.95 2.49 3.167 (4) 128
C1-H1B...Cg1ii 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


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

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011b). Cryst. Growth Des. 11, 1578-1596.  [CrossRef] [ChemPort]
Nayak, S. K., Venugopala, K. N., Chopra, D. & Guru Row, T. N. (2011a). CrystEngComm, 13, 591-605.  [CrossRef] [ChemPort]
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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Venugopala, K. N., Nayak, S. K. & Odhav, B. (2012). Acta Cryst. E68, o2977-o2978.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o123-o124   [ doi:10.1107/S1600536812050787 ]

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