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Volume 66 
Part 10 
Page o2602  
October 2010  

Received 14 September 2010
Accepted 16 September 2010
Online 25 September 2010

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.006 Å
R = 0.068
wR = 0.169
Data-to-parameter ratio = 17.3
Details
Open access

2,2'-(Disulfanediyl)dibenzoic acid-2,9-dimethylphenanthroline-tetrahydrofuran (1/2/1)

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The asymmetric unit of the title co-crystal solvate, C14H10O4S2·2C14H12N2·C4H8O, comprises a 2,2'-(disulfanediyl)dibenzoic acid molecule, two molecules of 2,9-dimethylphenanthroline and a tetrahydrofuran (THF) solvent molecule. Each end of the twisted diacid [dihedral angle between the benzene rings = 74.33 (17)°] forms a strong O-H...N hydrogen bond with a 2,9-dimethylphenanthroline molecule, forming a trimeric aggregate. The crystal structure comprises layers of acid and THF molecules, and layers of 2,9-dimethylphenanthroline molecules that alternate along the a axis, the main connections between them being of the type C-H...O.

Related literature

For related studies on co-crystal formation involving 2-[(2-carboxyphenyl)disulfanyl]benzoic acid, see: Broker & Tiekink (2007[Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096-1109.], 2010[Broker, G. A. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o705.]); Broker et al. (2008[Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879-887.]). For a co-crystal involving 2,9-dimethylphenanthroline, see: Arman et al. (2010[Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2117.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10O4S2·2C14H12N2·C4H8O

  • Mr = 794.96

  • Monoclinic, P 21

  • a = 14.011 (4) Å

  • b = 8.516 (3) Å

  • c = 17.403 (5) Å

  • [beta] = 109.637 (6)°

  • V = 1955.7 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 98 K

  • 0.26 × 0.21 × 0.10 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • 13023 measured reflections

  • 8637 independent reflections

  • 7988 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.169

  • S = 1.05

  • 8637 reflections

  • 499 parameters

  • 8 restraints

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

  • [Delta][rho]max = 0.83 e Å-3

  • [Delta][rho]min = -0.85 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3550 Friedel pairs

  • Flack parameter: 0.01 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2o...N1i 0.85 (4) 1.91 (4) 2.734 (4) 163 (4)
O2-H2o...N2i 0.85 (4) 2.46 (4) 2.982 (5) 121 (4)
O4-H4o...N4ii 0.84 (4) 1.86 (3) 2.691 (4) 170 (4)
C19-H19...O1iii 0.95 2.59 3.448 (5) 150
C22-H22...O5 0.95 2.52 3.383 (7) 150
C23-H23...O3 0.95 2.56 3.345 (5) 140
Symmetry codes: (i) x-1, y, z; (ii) [-x+2, y-{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: SU2213 ).


References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2117.  [CSD] [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879-887.  [ISI] [CSD] [CrossRef] [ChemPort]
Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096-1109.  [ISI] [CSD] [CrossRef] [ChemPort]
Broker, G. A. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o705.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, o2602  [ doi:10.1107/S1600536810037165 ]

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