1,2-Di­hydro­spiro­[carbazole-3(4H),2′-[1,3]dioxolane]

Bjerrum, J.V.; Ulven, T.; Bond, A.D.

doi:10.1107/S1600536809005558

Volume 65
Part 3
Page o579
March 2009

Received 29 January 2009
Accepted 16 February 2009
Online 21 February 2009

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.080
Data-to-parameter ratio = 9.6
Details

1,2-Dihydrospiro[carbazole-3(4H),2'-[1,3]dioxolane]

Janni Vester Bjerrum,^a Trond Ulven ^a and Andrew D. Bond ^a ^*

^aUniversity of Southern Denmark, Department of Physics and Chemistry, Campusvej 55, 5230 Odense M, Denmark
Correspondence e-mail: adb@chem.sdu.dk

In the title compound, C₁₄H₁₅NO₂, the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the dioxolane ring points to one side of the carbazole plane. Neighbouring molecules form edge-to-face interactions in which the NH group is directed towards an adjacent carbazole unit, with a shortest HC contact of 2.72 Å. These interactions arrange the molecules into one-dimensional herringbone-type motifs, which pack so that the methylene groups of the dioxolane ring lie over the face of a neighbouring carbazole unit with a shortest HC contact of 2.85 Å.

Related literature

For background literature and synthesis details, see: Ulven & Kostenis (2006); Urrutia & Rodriguez (1999).

Experimental

Crystal data

C₁₄H₁₅NO₂
M_r = 229.27
Monoclinic, P 2₁
a = 9.3781 (6) Å
b = 6.1467 (4) Å
c = 10.5740 (7) Å
= 115.232 (2)°
V = 551.38 (6) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 180 K
0.50 × 0.50 × 0.40 mm

Data collection

Bruker-Nonius X8 APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.812, T_max = 0.964
7776 measured reflections
1485 independent reflections
1427 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.080
S = 1.05
1485 reflections
154 parameters
1 restraint
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AC1ⁱ	0.88	2.72	3.527 (2)	154
C14-H14AC12ⁱⁱ	0.99	2.85	3.518 (3)	126
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; 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: YA2088 ).

Acknowledgements

We are grateful to the Danish Natural Sciences Research Council and the Carlsberg Foundation for provision of the X-ray equipment.

References

Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ulven, T. & Kostenis, E. (2006). Curr. Top. Med. Chem. 6, 1427-1444.
Urrutia, A. & Rodriguez, J. G. (1999). Tetrahedron, 55, 11095-11108.

organic compounds