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Volume 69 
Part 7 
Pages o1067-o1068  
July 2013  

Received 29 May 2013
Accepted 31 May 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 13.0
Details
Open access

A co-crystal of 1,10-phenanthroline with boric acid: a novel aza-aromatic complex

aFlorida Gulf Coast University, Department of Chemistry and Mathematics, Fort Myers, FL 33965-6565, USA, and bUniversity of South Alabama, Department of Chemistry, Mobile, AL 36688-0002
Correspondence e-mail: jdavis@southalabama.edu

The title compound, C12H8N2·2B(OH)3, is best described as a host-guest complex in which the B(OH)3 molecules form a hydrogen-bonded cyclic network of layers parallel to the ab plane into which the 1,10-phenanthroline molecules are bound. An extensive network of hydrogen bonds are responsible for the crystal stability. No [pi]-stacking interactions occur between the 1,10-phenanthroline molecules.

Related literature

For the design and synthesis of novel systems of non-covalent hosts involving hydrogen bonds, see: Pedireddi et al. (1997[Pedireddi, V. R., Chatterjee, S., Ranganathan, A. & Rao, C. N. R. (1997). J. Am. Chem. Soc. 119, 10867-10868.]). In the field of supermolecular synthesis, recognition between the complementary functional groups is a main factor for the evaluation of influence of noncovalent interactions in the formation of specific architecture, see: Lehn (1990[Lehn, J. M. (1990). Angew. Chem. Int. Ed. 29, 1304-1319.]). The ability of the -B(OH)2 functionality to form a variety of hydrogen bonds through different conformations makes it a very suitable moiety for the synthesis of novel molecular complexes, see: Lee et al. (2005[Lee, S. O., Kariuki, B. M. & Harris, K. D. M. (2005). New. J. Chem. 29, 1266-1271.]). It is known to have an affinity for pyridyl N atoms, often forming O-H...N hydrogen bonds, as observed in some crystals of boronic acids with aza compounds (Talwelkar & Pedireddi, 2010[Talwelkar, M. & Pedireddi, V. R. (2010). Tetrahedron Lett. 51, 6901-6905.]). Non-covalent hosts are generally designed and synthesized by employing appropriate functional groups at required symmetry positions to form a cyclic network through the hydrogen bonds, see: Pedireddi (2001[Pedireddi, V. R. (2001). Cryst. Growth Des. 1, 383-385.]). This effect has been observed in simple molecular adducts such as 1,10-phenanthroline and water (Tian et al., 1995[Tian, Y.-P., Duan, C.-Y., Xu, X.-X. & You, X.-Z. (1995). Acta Cryst. C51, 2309-2312.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2·2BH3O3

  • Mr = 303.87

  • Triclinic, [P \overline 1]

  • a = 7.1390 (13) Å

  • b = 9.6189 (13) Å

  • c = 10.4756 (15) Å

  • [alpha] = 93.767 (11)°

  • [beta] = 101.546 (14)°

  • [gamma] = 90.644 (13)°

  • V = 703.05 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 295 K

  • 0.35 × 0.16 × 0.09 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan [CrysAlis PRO (Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) based on Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.956, Tmax = 1.000

  • 10473 measured reflections

  • 2580 independent reflections

  • 1972 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.02

  • 2580 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2 0.85 1.90 2.7360 (16) 169
O2-H2...N1 0.85 1.88 2.7132 (17) 167
O3-H3...O1i 0.85 1.86 2.7076 (15) 177
O4-H4...O3i 0.85 1.89 2.7286 (16) 16
O5-H5...O4ii 0.85 1.89 2.7355 (18) 179
O6-H6...O2iii 0.85 1.95 2.7946 (17) 172
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2011[Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); 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: EZ2287 ).


Acknowledgements

The authors acknowledge the National Science Foundation for their generous support (NSF-CAREER grant to RES, CHE-0846680).

References

Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Lee, S. O., Kariuki, B. M. & Harris, K. D. M. (2005). New. J. Chem. 29, 1266-1271.  [CSD] [CrossRef] [ChemPort]
Lehn, J. M. (1990). Angew. Chem. Int. Ed. 29, 1304-1319.
Oxford Diffraction (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Pedireddi, V. R. (2001). Cryst. Growth Des. 1, 383-385.  [CSD] [CrossRef] [ChemPort]
Pedireddi, V. R., Chatterjee, S., Ranganathan, A. & Rao, C. N. R. (1997). J. Am. Chem. Soc. 119, 10867-10868.  [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Talwelkar, M. & Pedireddi, V. R. (2010). Tetrahedron Lett. 51, 6901-6905.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Tian, Y.-P., Duan, C.-Y., Xu, X.-X. & You, X.-Z. (1995). Acta Cryst. C51, 2309-2312.  [CSD] [CrossRef] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1067-o1068   [ doi:10.1107/S1600536813015134 ]

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