N-(9,11-Dimeth­oxy-4-oxo-2,3,4,6,7,11b-hexa­hydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide

Fun, H.-K.; Kuntiyong, P.; Tuntiwachwuttikul, P.; Chantrapromma, S.

doi:10.1107/S1600536810050737

Volume 67
Part 1
Pages o113-o114
January 2011

Received 24 November 2010
Accepted 3 December 2010
Online 11 December 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 12.2
Details

N-(9,11-Dimethoxy-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide

Hoong-Kun Fun,^a ^*⁺ Punlop Kuntiyong,^b Pittaya Tuntiwachwuttikul ^b and Suchada Chantrapromma ^c ⁺⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, Faculty of Science, Silpakorn University, Rajamanka Nai Road, Muang Nakhon Pathom 73000, Thailand, and ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

The title schulzeine derivative, C₂₂H₂₄N₂O₄, crystallizes with two crystallographically independent molecules of almost identical conformation in the asymmetric unit. The tricyclic core of schulzeine has a fused-three-ring system comprising the tetrahydroisoquinoline and [delta] -lactam moieties. In both molecules, the pyridine ring adopts a twisted-boat conformation, whereas the lactam ring is in a boat conformation. The two methoxy groups are slightly twisted from the attached benzene ring [C-O-C-C torsion angles = -21.3 (2) and -20.5 (2)° in molecule A, and -6.3 (2) and -16.2 (2)° in molecule B] and the benzamide moiety is in a (-)-synclinal conformation with respect to the lactam ring. In the crystal, molecules are linked into V-shaped dimers by intermolecular N-HO hydrogen bonds and weak C-HO interactions. These dimers are stacked into V-shaped columns along the a axis. Adjacent columns are further linked in an antiparallel manner. C-H [pi] interactions are also observed.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For background to schulzeines, see, for example: Kuntiyong et al. (2006); Melo et al. (2006); Takada et al. (2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₂H₂₄N₂O₄
M_r = 380.43
Orthorhombic, P 2₁ 2₁ 2₁
a = 12.6530 (3) Å
b = 15.5256 (4) Å
c = 19.7819 (5) Å
V = 3886.06 (17) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.56 × 0.44 × 0.41 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.952, T_max = 0.964
110999 measured reflections
6224 independent reflections
5979 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.098
S = 1.04
6224 reflections
509 parameters
H-atom parameters constrained
_max = 0.60 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A-C6A and C15A-C20A benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
N2A-H2AAO1Bⁱ	0.86	2.08	2.8994 (18)	158
N2B-H2BAO1Aⁱⁱ	0.86	2.24	2.9807 (18)	145
C1A-H1AAO4Bⁱⁱⁱ	0.93	2.52	3.405 (2)	160
C10A-H10BO3A	0.97	2.58	3.127 (2)	115
C3B-H3BAO4A^iv	0.93	2.49	3.348 (2)	153
C7B-H7BBO4A^v	0.97	2.47	3.407 (2)	163
C16A-H16AO1Bⁱ	0.93	2.32	3.228 (2)	165
C20B-H20BO1Aⁱⁱ	0.93	2.51	3.281 (2)	141
C22A-H22AO2A^iv	0.96	2.52	3.266 (2)	135
C22A-H22BO4B^vi	0.96	2.47	3.393 (2)	160
C22B-H22DO4A^iv	0.96	2.58	3.414 (2)	146
C11A-H11BCg2ⁱⁱ	0.97	2.78	3.686 (2)	156
C8B-H8BACg1^iv	0.97	2.60	3.4864 (17)	152
C18B-H18BCg1ⁱ	0.93	2.81	3.607 (2)	144
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) x, y+1, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x+1, y, z; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2531 ).

Acknowledgements

PK thanks the Thailand Research Fund (TRF) for financial support. SC thanks the Prince of Songkla University for generous support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

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.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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.
Kuntiyong, P., Akkarasmiyo, S. & Eksinitkun, G. (2006). Chem. Lett. 35, 1008-1009.
Melo, E. B., Gomes, A. S. & Carvalho, I. (2006). Tetrahedron, 62, 10277-10302.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Takada, K., Uehara, T., Nakao, Y., Matsunaga, S., van Soest, R. W. M. & Fusetani, N. (2004). J. Am. Chem. Soc. 126, 187-193.

organic compounds