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Volume 70 
Part 1 
Pages o59-o60  
January 2014  

Received 7 December 2013
Accepted 10 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.075
wR = 0.173
Data-to-parameter ratio = 18.7
Details
Open access

N-[(9H-Fluoren-9-yl­idene)(2-meth­oxy­phen­yl)meth­yl]-1,1,1-tri­methyl­silanamine

aSchool of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, People's Republic of China
Correspondence e-mail: chenxia@sxu.edu.cn

The title mol­ecule, C24H25NOSi, is a hydrolysis product of the reaction between 9-tri­methyl­silyfluorenyl lithium and 2-meth­oxy­benzo­nitrile. The fluorene ring system is substanti­ally planar, with an r.m.s. deviation of 0.0288 Å from the best-fit plane through its 13 C atoms. This plane forms a dihedral angle of 58.07 (7)° with the 2-meth­oxy­benzyl­amine ring plane. In the crystal, mol­ecules are linked by N-H...[pi] and C-H...[pi] inter­actions, which leads to the formation of two-dimensional network lying parallel to the bc plane.

Related literature

For the use of fluorene as a ligand in organometallic chemistry, see: Alt & Samuel (1998[Alt, H. G. & Samuel, E. (1998). Chem. Soc. Rev. 27, 323-329.]); Kirillov et al. (2005[Kirillov, E., Saillard, J. Y. & Carpentier, J. F. (2005). Coord. Chem. Rev. 249, 1221-1248.]); Bochmann et al. (1993[Bochmann, M., Lancaster, S. J., Hursthouse, M. B. & Mazid, M. (1993). Organometallics, 12, 4718-4720.]); Decken et al. (2002[Decken, A., Mackay, A. J., Brown, M. J. & Bottomley, F. (2002). Organometallics, 21, 2006-2009.]); Knjazhanski et al. (2002[Knjazhanski, S. Y., Cadenas, G., García, M., Pérez, C. M., Nifant'ev, I. E., Kashulin, I. A., Ivchenko, P. V. & Lyssenko, K. A. (2002). Organometallics, 21, 3094-3099.]); Novikova et al. (1985[Novikova, L. N., Ustynyuk, N. A., Zvorykin, V. E., Dneprovskaya, L. S. & Ustynyuk, Y. A. (1985). J. Organomet. Chem. 292, 237-243.]); Johnson & Treichel (1977[Johnson, J. W. & Treichel, P. M. (1977). J. Am. Chem. Soc. 99, 1427-1436.]). For [sigma]-[pi] stacking, see: Calhorda (2000[Calhorda, M. J. (2000). Chem. Commun. pp. 801-809.]); Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 152. Oxford University Press.]). For a related amino­fulvene structure, see: Axenov et al. (2009[Axenov, K. V., Kehr, G., Fröhlich, R. & Erker, G. (2009). Organometallics, 28, 5148-5158.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25NOSi

  • Mr = 371.54

  • Monoclinic, P 21 /c

  • a = 12.611 (3) Å

  • b = 9.5694 (19) Å

  • c = 20.325 (6) Å

  • [beta] = 124.10 (2)°

  • V = 2031.1 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 173 K

  • 0.19 × 0.17 × 0.12 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.985

  • 15991 measured reflections

  • 4628 independent reflections

  • 4212 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.173

  • S = 1.24

  • 4628 reflections

  • 248 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C1,C2,C7,C8,C13, C2-C7 and C15-C20 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1...Cg1i 0.88 2.69 3.347 (3) 133
C12-H12A...Cg4 0.95 2.99 3.750 (4) 138
C16-H16A...Cg2i 0.95 2.65 3.470 (3) 145
C21-H21C...Cg2ii 0.98 2.94 3.736 (4) 139
C24-H24A...Cg3i 0.98 2.99 3.923 (4) 158
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. 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: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5378 ).


Acknowledgements

We thank the Natural Science Foundation of China (grant No. 20942009, 21072120), the Shanxi Scholarship Council of China (No. 201310) and the Key Technologies R & D Program of Shanxi Province (No. 20110321055).

References

Alt, H. G. & Samuel, E. (1998). Chem. Soc. Rev. 27, 323-329.  [CrossRef] [ChemPort]
Axenov, K. V., Kehr, G., Fröhlich, R. & Erker, G. (2009). Organometallics, 28, 5148-5158.  [CSD] [CrossRef] [ChemPort]
Bochmann, M., Lancaster, S. J., Hursthouse, M. B. & Mazid, M. (1993). Organometallics, 12, 4718-4720.  [CSD] [CrossRef] [ChemPort]
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Calhorda, M. J. (2000). Chem. Commun. pp. 801-809.  [CrossRef]
Decken, A., Mackay, A. J., Brown, M. J. & Bottomley, F. (2002). Organometallics, 21, 2006-2009.  [CSD] [CrossRef] [ChemPort]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 152. Oxford University Press.
Johnson, J. W. & Treichel, P. M. (1977). J. Am. Chem. Soc. 99, 1427-1436.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Kirillov, E., Saillard, J. Y. & Carpentier, J. F. (2005). Coord. Chem. Rev. 249, 1221-1248.  [Web of Science] [CrossRef] [ChemPort]
Knjazhanski, S. Y., Cadenas, G., García, M., Pérez, C. M., Nifant'ev, I. E., Kashulin, I. A., Ivchenko, P. V. & Lyssenko, K. A. (2002). Organometallics, 21, 3094-3099.  [CSD] [CrossRef] [ChemPort]
Novikova, L. N., Ustynyuk, N. A., Zvorykin, V. E., Dneprovskaya, L. S. & Ustynyuk, Y. A. (1985). J. Organomet. Chem. 292, 237-243.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o59-o60   [ doi:10.1107/S1600536813033424 ]

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