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Volume 69 
Part 8 
Pages o1192-o1193  
August 2013  

Received 20 June 2013
Accepted 26 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.059
wR = 0.191
Data-to-parameter ratio = 14.5
Details
Open access

2-[1'-(Benzyloxy)spiro[indane-1,2'-pyrrolidine]-5'-yl]acetonitrile

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C21H22N2O, the planes of the two six-membered rings make a dihedral angle of 89.51 (7)°. The pyrrolidine ring has a puckering amplitude q2 = 0.418 (3) and a pseudo-rotation phase angle [varphi]2 = -166.8 (5), adopting a twist conformation (T). The other five-membered ring has a puckering amplitude q2 = 0.247 (2) and a pseudo-rotation phase angle [varphi]2 = -173.7 (5), adopting an envelope conformation with the CH2 atom adjacent to the C atom common with the pyrrolidine ring as the flap. In the crystal, molecules are linked via C-H...N, enclosing R22(20) rings, forming chains propagating along [100]. The acetonitrile group is disordered over two positions and was refined with a fixed occupancy ratio of 0.56:0.44.

Related literature

For radical cyclization of 1-azaspiro compounds, see: El Bialy et al. (2004[El Bialy, S. A. A., Braun, H. & Tietze, L. F. (2004). Synthesis, pp. 2249-2262.]); Dake (2006[Dake, G. (2006). Tetrahedron, 62, 3467-3492.]). For cephalotaxine synthesis, see: Paudler et al. (1963[Paudler, W. W., Kerley, G. I. & McKay, J. (1963). J. Org. Chem. 28, 2194-2197.]); Planas et al. (2004[Planas, L., Pérard-Viret, J. & Royer, J. (2004). J. Org. Chem. 69, 3087-3092.]). For esters with antileukemic activity, see: Benderra et al. (1998[Benderra, Z., Morjani, H., Trussardi, A. & Manfait, M. (1998). Leukemia, 12, 1539-1544.]); Kantarjian et al. (2001[Kantarjian, H. M., Talpaz, M., Santini, V., Murgo, A., Cheson, B. & O'Brien, S. M. (2001). Cancer, 92, 1591-1605.]); Lévy et al. (2006[Lévy, V., Zohar, S., Bardin, C., Vekhoff, A., Chaoui, D., Rio, B., Legrand, O., Sentenac, S., Rousselot, P., Raffoux, E., Chast, F., Chevret, S. & Marie, J. P. (2006). Br. J. Cancer, 95, 253-259.]). For pyrrolidine properties, see: Chen et al. (2012[Chen, J., Zhou, L. & Yeung, Y.-Y. (2012). Org. Biomol. Chem. 10, 3808-3811.]); Boyd et al. (1999[Boyd, S. A., Mantei, R. A., Tasker, A. S., Liu, G., Sorensen, B. K., Henry, K. J. Jr, von Geldern, T. W., Winn, M., Wu-Wong, J. R., Chiou, W. J., Dixon, D. B., Hutchins, C. W., Marsh, K. C., Nguyen, B. & Opgenorth, T. J. (1999). Bioorg. Med. Chem. 7, 991-1002.]). For tandem reactions under radical conditions, see: Jaramillo-Gómez et al. (2006[Jaramillo-Gómez, L. M., Loaiza, A. E., Martin, J., Ríos, L. A. & Wang, P. G. (2006). Tetrahedron Lett. 47, 3909-3912.]). For bond-length data, see: Allen et al. (1987[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.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and for hydrogen-bond motifs, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]). For ring torsion angles, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C21H22N2O

  • Mr = 318.41

  • Triclinic, [P \overline 1]

  • a = 9.1688 (4) Å

  • b = 10.0800 (4) Å

  • c = 11.4141 (6) Å

  • [alpha] = 98.826 (2)°

  • [beta] = 108.777 (2)°

  • [gamma] = 110.403 (4)°

  • V = 893.17 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 295 K

  • 0.29 × 0.25 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 6429 measured reflections

  • 3617 independent reflections

  • 2307 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.191

  • S = 1.05

  • 3617 reflections

  • 249 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21...N2Bi 0.93 2.61 3.511 (15) 164
C21-H21...N2Ai 0.93 2.48 3.390 (18) 168
Symmetry codes: (i) -x+2, -y+2, -z+1.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5325 ).


Acknowledgements

RMF and LMJG are grateful to the Universidad del Valle, Colombia, for partial financial support.

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.
Benderra, Z., Morjani, H., Trussardi, A. & Manfait, M. (1998). Leukemia, 12, 1539-1544.  [Web of Science] [ChemPort] [PubMed]
Boyd, S. A., Mantei, R. A., Tasker, A. S., Liu, G., Sorensen, B. K., Henry, K. J. Jr, von Geldern, T. W., Winn, M., Wu-Wong, J. R., Chiou, W. J., Dixon, D. B., Hutchins, C. W., Marsh, K. C., Nguyen, B. & Opgenorth, T. J. (1999). Bioorg. Med. Chem. 7, 991-1002.  [CrossRef] [PubMed] [ChemPort]
Chen, J., Zhou, L. & Yeung, Y.-Y. (2012). Org. Biomol. Chem. 10, 3808-3811.  [CSD] [CrossRef] [ChemPort] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dake, G. (2006). Tetrahedron, 62, 3467-3492.  [Web of Science] [CrossRef] [ChemPort]
El Bialy, S. A. A., Braun, H. & Tietze, L. F. (2004). Synthesis, pp. 2249-2262.
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jaramillo-Gómez, L. M., Loaiza, A. E., Martin, J., Ríos, L. A. & Wang, P. G. (2006). Tetrahedron Lett. 47, 3909-3912.
Kantarjian, H. M., Talpaz, M., Santini, V., Murgo, A., Cheson, B. & O'Brien, S. M. (2001). Cancer, 92, 1591-1605.  [CrossRef] [PubMed] [ChemPort]
Lévy, V., Zohar, S., Bardin, C., Vekhoff, A., Chaoui, D., Rio, B., Legrand, O., Sentenac, S., Rousselot, P., Raffoux, E., Chast, F., Chevret, S. & Marie, J. P. (2006). Br. J. Cancer, 95, 253-259.  [Web of Science] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Paudler, W. W., Kerley, G. I. & McKay, J. (1963). J. Org. Chem. 28, 2194-2197.  [CrossRef] [ChemPort]
Planas, L., Pérard-Viret, J. & Royer, J. (2004). J. Org. Chem. 69, 3087-3092.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1192-o1193   [ doi:10.1107/S1600536813017674 ]

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