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Volume 68 
Part 11 
Page o3070  
November 2012  

Received 18 September 2012
Accepted 28 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.147
Data-to-parameter ratio = 24.5
Details
Open access

(N[rightwards arrow]B)-4-Methyl-3-pyridyl[N-methyliminodiacetate-O,O',N]borane

aPhysical Chemistry Department, Faculty of Chemistry, Warsaw University of, Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Correspondence e-mail: kdurka@ch.pw.edu.pl

The title compound, C11H13BN2O4, has a rigid bicyclic structure due to an intramolecular nitrogen-boron dative bond. The B atom is in a distorted tetrahedron environment with a B-N bond length of 1.640 (2) Å, which is in good comparison with the values in analogues compounds. In the crystal, the molecules are linked by weak C-H...O and C-H...N interactions, forming a three-dimensional network.

Related literature

For related structures of [N-alkyliminodiacetate-O,O',N]boranes, see: Mancilla et al. (1997[Mancilla, T., Höp, H., Bravo, G. & Carrillo, L. (1997). Main Group Met. Chem. 20, 31-36.], 2005[Mancilla, T., Zamudio Rivera, L. S., Beltrán, H. I., Santillán, R. & Farfn, N. (2005). Arkivoc, iv, 366-376.]); Gillis & Burke (2008[Gillis, E. P. & Burke, M. D. (2008). J. Am. Chem. Soc. 130, 14084-14085.]); Knapp et al. (2009[Knapp, D. M., Gillis, E. P. & Burke, M. D. (2009). J. Am. Chem. Soc. 131, 6961-6963.]); Percino et al. (2009[Percino, T. M., Ancona, R. M. F. & Martinez, M. L. (2009). Polyhedron, 28, 2771-2775.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13BN2O4

  • Mr = 248.04

  • Monoclinic, P 21 /n

  • a = 7.306 (3) Å

  • b = 14.7425 (4) Å

  • c = 10.8281 (19) Å

  • [beta] = 96.91 (4)°

  • V = 1157.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.16 × 0.12 × 0.10 mm

Data collection
  • Agilent Xcalibur Opal diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Santa Clara, United States.]) Tmin = 0.910, Tmax = 0.989

  • 26273 measured reflections

  • 3993 independent reflections

  • 3148 reflections with I > 2[sigma](I)

  • Rint = 0.075

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.147

  • S = 1.07

  • 3993 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H10A...O4i 0.99 2.42 3.356 (1) 158
C11-H12B...N1ii 0.98 2.64 3.509 (1) 149
C11-H12A...O4i 0.98 2.40 3.259 (1) 146
C10-H8A...O3iii 0.99 2.28 3.247 (1) 165
C11-H12C...O2iv 0.98 2.57 3.500 (1) 158
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x-1, y, z; (iii) -x, -y, -z+1; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Santa Clara, United States.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005[Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5196 ).


Acknowledgements

The X-ray measurements were undertaken in the Crystallographic Unit of the Physical Chemistry Laboratory at the Chemistry Department of the University of Warsaw. This work was supported by the Aldrich Chemical Co. through donation of chemicals and equipment and by the Warsaw University of Technology.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Santa Clara, United States.
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Gillis, E. P. & Burke, M. D. (2008). J. Am. Chem. Soc. 130, 14084-14085.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Knapp, D. M., Gillis, E. P. & Burke, M. D. (2009). J. Am. Chem. Soc. 131, 6961-6963.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Mancilla, T., Höp, H., Bravo, G. & Carrillo, L. (1997). Main Group Met. Chem. 20, 31-36.  [CrossRef] [ChemPort]
Mancilla, T., Zamudio Rivera, L. S., Beltrán, H. I., Santillán, R. & Farfn, N. (2005). Arkivoc, iv, 366-376.
Percino, T. M., Ancona, R. M. F. & Martinez, M. L. (2009). Polyhedron, 28, 2771-2775.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3070  [ doi:10.1107/S1600536812040974 ]

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