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Volume 66 
Part 4 
Page o758  
April 2010  

Received 25 February 2010
Accepted 28 February 2010
Online 6 March 2010

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.061
wR = 0.127
Data-to-parameter ratio = 15.1
Details
Open access

{2-Hydroxy-6-[(2-oxidophenyl)iminomethyl-[kappa]2N,O]phenolato-[kappa]O1}phenylboron

Araceli Vega,a Hugo Tlahuexta and Herbert Höpfla*

aCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Col. Chamilpa, CP 62209, Cuernavaca Mor., Mexico
Correspondence e-mail: hhopfl@uaem.mx

The [4.3.0]heterobicyclic title structure, C19H14BNO3, is composed of a five-membered OBNC2 ring and a six-membered OBNC3 ring, each of which has an approximate envelope conformation. The coordination geometry of the B atom is distorted tetrahedral. In the crystal structure, centrosymmetrically related molecules are associated through pairs of O-H...O hydrogen bonds.

Related literature

For related boronates, see: Barba et al. (2001[Barba, V., Cuahutle, D., Santillan, R. & Farfán, N. (2001). Can. J. Chem. 79, 1229-1237.]); Höpfl et al. (1998[Höpfl, H., Sánchez, M., Farfán, N. & Barba, V. (1998). Can. J. Chem. 76, 1352-1360.]); Lamère et al. (2006[Lamère, J. F., Lacroix, P. G., Farfán, N., Rivera, J. M., Santillan, R. & Nakatani, K. (2006). J. Mater. Chem. 16, 2913-2920.]). For boronates with non-linear optical properties, see: Reyes et al. (2005[Reyes, H., Rivera, J. M., Farfán, N., Santillan, R., Lacroix, P. G., Lepetit, C. & Nakatani, K. (2005). J. Organomet. Chem. 690, 3737-3745.]); Muñoz et al. (2008[Muñoz, B. M., Santillan, R., Rodríguez, M., Méndez, J. M., Romero, M., Farfán, N., Lacroix, P. G., Nakatani, K., Ramos-Ortíz, G. & Maldonado, J. L. (2008). J. Organomet. Chem. 693, 1321-1334.]). For the use of boronates in organic synthesis, see: Rodríguez et al. (2005a[Rodríguez, M., Ochoa, M. E., Rodríguez, C., Santillan, R., Barba, V. & Farfán, N. (2005a). J. Organomet. Chem. 692, 2425-2435.],b[Rodríguez, M., Ochoa, M. E., Santillan, R., Farfán, N. & Barba, V. (2005b). J. Organomet. Chem. 692, 2975-2988.]); López-Ruiz et al. (2008[López-Ruiz, H., Mera-Moreno, I., Rojas-Lima, S., Santillan, R. & Farfán, N. (2008). Tetrahedron Lett. 49, 1674-1677.]). For a definition of the tetrahedral character in boron compounds, see: Höpfl et al. (1999[Höpfl, H. (1999). J. Organomet. Chem. 581, 129-149.]).

[Scheme 1]

Experimental

Crystal data

  • C19H14BNO3

  • Mr = 315.12

  • Orthorhombic, P b c a

  • a = 14.7245 (13) Å

  • b = 11.196 (1) Å

  • c = 18.4060 (16) Å

  • V = 3034.3 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.21 × 0.20 × 0.16 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.985

  • 31865 measured reflections

  • 3317 independent reflections

  • 1942 reflections with I > 2[sigma](I)

  • Rint = 0.088
Refinement

  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.127

  • S = 1.09

  • 3317 reflections

  • 220 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3'...O2i 0.84 (2) 1.97 (2) 2.740 (2) 152 (3)
C7-H7...O3ii 0.93 2.53 3.165 (3) 126
Symmetry codes: (i) -x, -y+2, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART. Bruker AXS Inc, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus NT (Bruker, 2001[Bruker (2001). SAINT-Plus NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus NT; 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: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2636 ).

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CIAM-59213).

References

Barba, V., Cuahutle, D., Santillan, R. & Farfán, N. (2001). Can. J. Chem. 79, 1229-1237.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2000). SMART. Bruker AXS Inc, Madison, Wisconsin, USA.
Bruker (2001). SAINT-Plus NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Höpfl, H. (1999). J. Organomet. Chem. 581, 129-149.
Höpfl, H., Sánchez, M., Farfán, N. & Barba, V. (1998). Can. J. Chem. 76, 1352-1360.
Lamère, J. F., Lacroix, P. G., Farfán, N., Rivera, J. M., Santillan, R. & Nakatani, K. (2006). J. Mater. Chem. 16, 2913-2920.
López-Ruiz, H., Mera-Moreno, I., Rojas-Lima, S., Santillan, R. & Farfán, N. (2008). Tetrahedron Lett. 49, 1674-1677.
Muñoz, B. M., Santillan, R., Rodríguez, M., Méndez, J. M., Romero, M., Farfán, N., Lacroix, P. G., Nakatani, K., Ramos-Ortíz, G. & Maldonado, J. L. (2008). J. Organomet. Chem. 693, 1321-1334.
Reyes, H., Rivera, J. M., Farfán, N., Santillan, R., Lacroix, P. G., Lepetit, C. & Nakatani, K. (2005). J. Organomet. Chem. 690, 3737-3745.  [CSD] [CrossRef] [ChemPort]
Rodríguez, M., Ochoa, M. E., Rodríguez, C., Santillan, R., Barba, V. & Farfán, N. (2005a). J. Organomet. Chem. 692, 2425-2435.
Rodríguez, M., Ochoa, M. E., Santillan, R., Farfán, N. & Barba, V. (2005b). J. Organomet. Chem. 692, 2975-2988.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). publCIF. In preparation.

Acta Cryst (2010). E66, o758  [ doi:10.1107/S1600536810007609 ]

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