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Volume 66 
Part 10 
Page o2646  
October 2010  

Received 7 September 2010
Accepted 21 September 2010
Online 30 September 2010

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Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.112
Data-to-parameter ratio = 10.0
Details
Open access

[2,2'-Iminodiethanolato(2-)-[kappa]3O,N,O'][4-(methoxycarbonylmethyl)phenyl]boron

Ahmed L. Zein,a Louise N. Dawea and Paris E. Georghioua*

aDepartment of Chemistry, Memorial University of Newfoundland, St Johns, NL, Canada A1B 3X7
Correspondence e-mail: parisg@mun.ca

The title compound, C13H18BNO4, was readily obtained from the reaction of methyl 4-boronobenzene acetate with ethanolamine. A combination of intermolecular N-H...O hydrogen bonds and C-H...[pi] interactions leads to the pairwise association of molecules.

Related literature

For background to the biological importance of boron, see: Warrington (1923[Warrington, K. (1923). Ann. Bot. 37, 629-672.]); Jabbour et al. (2004[Jabbour, A., Steinberg, D., Valery, M. D., Moussaieff, A., Zaks, B. & Srebnik, M. (2004). J. Med. Chem. 47, 2409-2410.]). For the use of boron-containing reagents in synthetic chemistry, see: Miyaura & Suzuki (1995[Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.]); Corey et al. (1987[Corey, E. J., Bakshi, R. K. & Shibata, S. (1987). J. Am. Chem. Soc. 109, 5553-5554.]); Liu et al. (2007[Liu, D., Canales, E. & Corey, E. J. (2007). J. Am. Chem. Soc. 129, 1498-1499.]); Jung & Lazarova (1999[Jung, M. E. & Lazarova, T. I. (1999). J. Org. Chem. 64, 2976-2977.]); Chan et al. (1998[Chan, D. M. T., Monaco, K. L., Wang, R. P. & Winters, M. P. (1998). Tetrahedron Lett. 39, 2933-2936.]); Evans et al. (1998[Evans, D. A., Katz, J. L. & West, T. R. (1998). Tetrahedron Lett. 39, 2937-2940.]); Lam et al. (1998[Lam, P. Y. S., Clark, C. G., Saubern, S., Adams, J., Winters, M. P., Chan, D. M. T. & Combs, A. (1998). Tetrahedron Lett. 39, 2941-2944.]). For related structures, see: Rettig & Trotter (1975[Rettig, S. J. & Trotter, J. (1975). Can. J. Chem. 53, 1393-1401.]); Wang & Georghiou (2002[Wang, Y.-C. & Georghiou, P. E. (2002). Org. Lett. 4, 2675-2678.]).

[Scheme 1]

Experimental

Crystal data

  • C13H18BNO4

  • Mr = 263.10

  • Orthorhombic, P 21 21 21

  • a = 8.3776 (11) Å

  • b = 8.9269 (11) Å

  • c = 17.369 (2) Å

  • V = 1299.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 153 K

  • 0.30 × 0.09 × 0.06 mm
Data collection

  • Rigaku Saturn diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo.]) Tmin = 0.985, Tmax = 0.997

  • 16363 measured reflections

  • 1725 independent reflections

  • 1707 reflections with I > 2[sigma](I)

  • Rint = 0.037
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.112

  • S = 1.17

  • 1725 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1-C6 ring.
D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.93 2.06 2.921 (2) 154
C10-H10B...Cg3ii 0.99 2.65 3.618 (2) 166
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2002[Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2337 ).

Acknowledgements

We thank the NSERC and the Department of Chemistry for financial support. We are also grateful to the Ministry for Higher Education, Egypt, for a scholarship to ALZ.

References

Chan, D. M. T., Monaco, K. L., Wang, R. P. & Winters, M. P. (1998). Tetrahedron Lett. 39, 2933-2936.  [CrossRef]
Corey, E. J., Bakshi, R. K. & Shibata, S. (1987). J. Am. Chem. Soc. 109, 5553-5554.
Evans, D. A., Katz, J. L. & West, T. R. (1998). Tetrahedron Lett. 39, 2937-2940.  [CrossRef]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo.
Jabbour, A., Steinberg, D., Valery, M. D., Moussaieff, A., Zaks, B. & Srebnik, M. (2004). J. Med. Chem. 47, 2409-2410.  [CrossRef]
Jung, M. E. & Lazarova, T. I. (1999). J. Org. Chem. 64, 2976-2977.  [CrossRef]
Lam, P. Y. S., Clark, C. G., Saubern, S., Adams, J., Winters, M. P., Chan, D. M. T. & Combs, A. (1998). Tetrahedron Lett. 39, 2941-2944.  [CrossRef]
Liu, D., Canales, E. & Corey, E. J. (2007). J. Am. Chem. Soc. 129, 1498-1499.  [CrossRef]
Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.  [ISI] [CrossRef] [ChemPort]
Rettig, S. J. & Trotter, J. (1975). Can. J. Chem. 53, 1393-1401.  [CrossRef] [ChemPort] [ISI]
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, Y.-C. & Georghiou, P. E. (2002). Org. Lett. 4, 2675-2678.  [CrossRef]
Warrington, K. (1923). Ann. Bot. 37, 629-672.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2010). E66, o2646  [ doi:10.1107/S1600536810037864 ]

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