8H-Chromeno[2′,3′:4,5]imidazo[2,1-a]isoquinoline

Safarov, S.; Voskressensky, L.G.; Bizhko, O.V.; Kulikova, L.N.; Khrustalev, V.N.

doi:10.1107/S1600536810006744

Volume 66
Part 3
Page o710
March 2010

Received 19 February 2010
Accepted 22 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.066
wR = 0.182
Data-to-parameter ratio = 14.4
Details

8H-Chromeno[2',3':4,5]imidazo[2,1-a]isoquinoline

Saifidin Safarov,^a ^* Leonid G. Voskressensky,^b Oksana V. Bizhko,^b Larisa N. Kulikova ^b and Victor N. Khrustalev ^c

^aV. I. Nikitin Institute of Chemistry, Ayni St. 299/2, Dushanbe 734063, Tajikistan,^bOrganic Chemistry Department, Russian Peoples Friendship University, Miklukho-Maklai St 6, Moscow 117198, Russian Federation, and ^cA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St 28, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: vkh@xray.ineos.ac.ru

The title compound, C₁₈H₁₂N₂O, comprises two aromatic fragments, viz., imidazo[2,1-a]isoquinoline and benzene, linked by oxygen and methylene bridges. Despite the absence of a common conjugative system within the molecule, it adopts an essentially planar conformation with an r.m.s. deviation of 0. 036 Å. In the crystal, due to this structure, molecules form stacks along the b axis by [pi] [pi] stacking interactions, with shortest CC distances in the range 3.340 (4)-3.510 (4) Å. The molecules are bound by intermolecular C-HO interactions within the stacks and C-H [pi] interactions between the stacks.

Related literature

For background to cascade reactions, see: Bunce (1995); Tietze (1996); Parsons et al. (1996); Nicolaou et al. (2003, 2006); Wasilke et al. (2005); Pellissier (2006a,b); Parenty & Cronin (2008). For related compounds, see: Yadav et al. (2007); Kianmehr et al. (2009); Surpur et al. (2009).

Experimental

Crystal data

C₁₈H₁₂N₂O
M_r = 272.30
Monoclinic, P 2₁ /n
a = 11.9717 (15) Å
b = 6.0580 (8) Å
c = 17.948 (2) Å
= 102.682 (3)°
V = 1269.9 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.40 × 0.12 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.965, T_max = 0.998
12413 measured reflections
2734 independent reflections
1821 reflections with I > 2(I)
R_int = 0.056

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.182
S = 1.00
2734 reflections
190 parameters
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the O13,C12A,C8A,C8,C7A,C13A ring.

D-HA	D-H	HA	DA	D-HA
C8-H8AO13ⁱ	0.99	2.71	3.637 (4)	157
C8-H8BCgⁱⁱ	0.99	2.63	3.547 (3)	154
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2193 ).

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bunce, R. A. (1995). Tetrahedron, 51, 13103-13159.
Kianmehr, E., Faramarzi, R. & Estiri, H. (2009). Heterocycles, 78, 415-423.
Nicolaou, K. C., Edmonds, D. J. & Bulger, P. G. (2006). Angew. Chem. Int. Ed. 45, 7134-7186.
Nicolaou, K. C., Montagnon, T. & Snyder, S. A. (2003). Chem. Commun. pp. 551-564.
Parenty, A. D. C. & Cronin, L. (2008). Synthesis, pp. 1479-1485.
Parsons, P. J., Penkett, C. S. & Shell, A. J. (1996). Chem. Rev. 96, 195-206.
Pellissier, H. (2006a). Tetrahedron, 62, 1619-1665.
Pellissier, H. (2006b). Tetrahedron, 62, 2143-2173.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Surpur, M. P., Kshirsagar, S. & Samant, S. D. (2009). Tetrahedron Lett. 50, 719-722.
Tietze, L. F. (1996). Chem. Rev. 96, 115-136.
Wasilke, J.-C., Obrey, S. J., Baker, R. T. & Bazan, G. C. (2005). Chem. Rev. 105, 1001-1020.
Yadav, J. S., Subba Reddy, B. V., Gupta, M. K., Prathap, I. & Pandey, S. K. (2007). Catal. Commun. 8, 2208-2211.

organic compounds