(N→B)-4-Methyl-3-pyrid­yl[N-methyl­imino­diacetate-O,O′,N]borane

Dąbrowski, M.; Durka, K.; Serwatowski, J.

doi:10.1107/S1600536812040974

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 (C-C) = 0.002 Å
R = 0.052
wR = 0.147
Data-to-parameter ratio = 24.5
Details

(NB)-4-Methyl-3-pyridyl[N-methyliminodiacetate-O,O',N]borane

Marek Dabrowski,^a Krzysztof Durka ^a ^* and Janusz Serwatowski ^a

^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-HO and C-HN interactions, forming a three-dimensional network.

Related literature

For related structures of [N-alkyliminodiacetate-O,O',N]boranes, see: Mancilla et al. (1997, 2005); Gillis & Burke (2008); Knapp et al. (2009); Percino et al. (2009).

Experimental

Crystal data

C₁₁H₁₃BN₂O₄
M_r = 248.04
Monoclinic, P 2₁ /n
a = 7.306 (3) Å
b = 14.7425 (4) Å
c = 10.8281 (19) Å
= 96.91 (4)°
V = 1157.8 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.910, T_max = 0.989
26273 measured reflections
3993 independent reflections
3148 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.147
S = 1.07
3993 reflections
163 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H10AO4ⁱ	0.99	2.42	3.356 (1)	158
C11-H12BN1ⁱⁱ	0.98	2.64	3.509 (1)	149
C11-H12AO4ⁱ	0.98	2.40	3.259 (1)	146
C10-H8AO3ⁱⁱⁱ	0.99	2.28	3.247 (1)	165
C11-H12CO2^iv	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Knapp, D. M., Gillis, E. P. & Burke, M. D. (2009). J. Am. Chem. Soc. 131, 6961-6963.
Mancilla, T., Höp, H., Bravo, G. & Carrillo, L. (1997). Main Group Met. Chem. 20, 31-36.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds