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Volume 69 
Part 6 
Page m333  
June 2013  

Received 30 April 2013
Accepted 14 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.020
wR = 0.050
Data-to-parameter ratio = 17.7
Details
Open access

Bis(but-2-enoato-[kappa]O)triphenylbismuth(V)

aDepartment of Physics, N. I. Lobachevsky State University of Nizhni Novgorod, 603950, pr. Gagarina, 23-3 Nizhni Novgorod, Russia, and bDepartment of Chemistry, N. I. Lobachevsky State University of Nizhni Novgorod, 603950, pr. Gagarina, 23-2 Nizhni Novgorod, Russia
Correspondence e-mail: andreev@phys.unn.ru

In the title molecule, [Bi(C6H5)3(C4H5O2)2], the BiV atom is in a distorted trigonal-bipyramidal environment with carboxylate O atoms in axial positions and phenyl C atoms in the equatorial plane. The Bi-O bond lengths are 2.283 (3) and 2.309 (2) Å, but as a result of additional long Bi...O interactions [2.787 (3) and 2.734 (3) Å], one of the C-Bi-C angles is 148.62 (13)°. In the crystal, weak C-H...O hydrogen bonds connect pairs of molecules into inversion dimers. These dimers are further connected by weak C-H...[pi] interactions into chains along [100] .

Related literature

For the isotypic (C6H5)3Sb(C4H5O2)2 structure, see: Gushchin et al. (2013[Gushchin, A. V., Kalistratova, O. S., Verkhovykh, R. A., Somov, N. V., Shashkin, D. V. & Dodonov, V. A. (2013). Vestn. NNovg. Univ. 1, 86-90. ]). For closely related structures, see: Andreev et al. (2013[Andreev, P. V., Somov, N. V., Kalistratova, O. S., Gushchin, A. V. & Chuprunov, E. V. (2013). Acta Cryst. E69, m167.]); Belsky (1996[Belsky, V. K. (1996). Private communication (refcode NAGXOI). CCDC, Cambridge, England.]). For the chemistry of triphenyantimony diacylates, see: Gushchin et al. (2011[Gushchin, A. V., Shashkin, D. V., Prytkova, L. K., Somov, N. V., Baranov, E. V., Shavyrin, A. S. & Rykalin, V. I. (2011). Russ. J. General Chem. 81, 493-496.]), for their thermodynamic properties, see: Letyanina et al. (2012[Letyanina, I. A., Markin, A. V., Smirnova, N. N., Gushchin, A. V. & Shashkin, D. V. (2012). Russ. J. Phys. Chem. A86, 1189-1195.]); Markin et al. (2011[Markin, A. V., Letyanina, I. A., Ruchenin, V. A., Smirnova, N. N., Gushchin, A. V. & Shashkin, D. V. (2011). J. Chem. Eng. Data, 56, 3657-3662.]) and for their applications, see: Dodonov & Gushchin (2004[Dodonov, V. A. & Gushchin, A. V. (2004). Vestn. NNovg. Univ. 82, 86-94.]). For van der Waals radii, see: Batsanov (2001[Batsanov, S. S. (2001). Inorg. Mater. 37, 871-885.]).

[Scheme 1]

Experimental

Crystal data
  • [Bi(C6H5)3(C4H5O2)2]

  • Mr = 610.44

  • Triclinic, [P \overline 1]

  • a = 10.4710 (3) Å

  • b = 10.4957 (3) Å

  • c = 11.9774 (3) Å

  • [alpha] = 84.941 (2)°

  • [beta] = 83.633 (2)°

  • [gamma] = 69.084 (3)°

  • V = 1220.32 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 7.25 mm-1

  • T = 293 K

  • 0.09 mm (radius)

Data collection
  • Agilent Xcalibur (Sapphire3, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.810, Tmax = 1

  • 17262 measured reflections

  • 4946 independent reflections

  • 4620 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.020

  • wR(F2) = 0.050

  • S = 1.11

  • 4946 reflections

  • 280 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.84 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2Ai 0.93 2.53 3.450 (6) 171
C4B-H4B1...C1Aii 0.96 2.74 3.683 (6) 167
C4B-H4B1...C2Aii 0.96 2.85 3.613 (7) 137
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: LH5612 ).


Acknowledgements

The work was supported financially by the Ministry of Education and Science of the Russian Federation, project 14.B37.21.1158.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Andreev, P. V., Somov, N. V., Kalistratova, O. S., Gushchin, A. V. & Chuprunov, E. V. (2013). Acta Cryst. E69, m167.  [CrossRef] [details]
Batsanov, S. S. (2001). Inorg. Mater. 37, 871-885.  [ISI] [CrossRef] [ChemPort]
Belsky, V. K. (1996). Private communication (refcode NAGXOI). CCDC, Cambridge, England.
Dodonov, V. A. & Gushchin, A. V. (2004). Vestn. NNovg. Univ. 82, 86-94.
Gushchin, A. V., Kalistratova, O. S., Verkhovykh, R. A., Somov, N. V., Shashkin, D. V. & Dodonov, V. A. (2013). Vestn. NNovg. Univ. 1, 86-90.
Gushchin, A. V., Shashkin, D. V., Prytkova, L. K., Somov, N. V., Baranov, E. V., Shavyrin, A. S. & Rykalin, V. I. (2011). Russ. J. General Chem. 81, 493-496.  [CrossRef] [ChemPort]
Letyanina, I. A., Markin, A. V., Smirnova, N. N., Gushchin, A. V. & Shashkin, D. V. (2012). Russ. J. Phys. Chem. A86, 1189-1195.  [ISI] [CrossRef]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Markin, A. V., Letyanina, I. A., Ruchenin, V. A., Smirnova, N. N., Gushchin, A. V. & Shashkin, D. V. (2011). J. Chem. Eng. Data, 56, 3657-3662.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m333  [ doi:10.1107/S1600536813013317 ]

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