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Volume 69 
Part 2 
Page o223  
February 2013  

Received 13 December 2012
Accepted 4 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.076
Data-to-parameter ratio = 8.2
Details
Open access

(S)-2,2'-Dihydroxy-N,N'-(6-hydroxyhexane-1,5-diyl)dibenzamide

aFachrichtung Chemie, Universität des Saarlandes, Postfach 151150, D-66041 Saarbrücken, Germany
Correspondence e-mail: hegetschweiler@mx.uni-saarland.de

In the title compound, C20H24N2O5, the dihedral angle between the two roughly planar salicylamide fragments [r.m.s. deviations = 0.043 (2) and 0.149 (2) Å] is 25.50 (5)°. The molecular conformation is stabilized by intramolecular O-H...O hydrogen bonds involving phenol -OH groups and amide O atoms. Intermolecular hydroxymethyl-amide O-H...O and amine-hydroxymethyl N-H...O hydrogen bonds form infinite chains along the b axis. These chains are further interlinked by amine-amide N-H...O and phenol-phenol O-H...O interactions, thus giving layers parallel to (001).

Related literature

For the isolation and physico-chemical properties of myxochelin A, see: Kunze et al. (1989[Kunze, B., Bedorf, N., Kohl, W., Höfle, G. & Reichenbach, H. (1989). J. Antibiot. 42, 14-17.]). For the crystal structure of N,N'-(pentane-1,5-diyl)bis(3-methoxysalicylamide), see: Huang et al. (1995[Huang, S.-P., Franz, K. J., Olmstead, M. M. & Fish, R. H. (1995). Inorg. Chem. 34, 2820-2825.]). For metal complex formation with linear bis-catechol amides and linear bis-salicylamides, see: Duhme et al. (1996[Duhme, A.-K., Dauter, Z., Hider, R. C. & Pohl, S. (1996). Inorg. Chem. 35, 3059-3061.]); Huang et al. (1995[Huang, S.-P., Franz, K. J., Olmstead, M. M. & Fish, R. H. (1995). Inorg. Chem. 34, 2820-2825.]); Cappillino et al. (2009[Cappillino, P. J., Tarves, P. C., Rowe, G. T., Lewis, A. J., Harvey, M., Rogge, C., Stassinopoulos, A., Lo, W., Armstrong, W. H. & Caradonna, J. P. (2009). Inorg. Chim. Acta, 362, 2136-2150.]); Stoicescu et al. (2009[Stoicescu, L., Duhayon, C., Vendier, L., Tesouro-Vallina, A., Costes, J.-P. & Tuchagues, J.-P. (2009). Eur. J. Inorg. Chem. pp. 5483-5493.]). For the treatment of H atoms in SHELXL, see: Müller et al. (2006[Müller, P., Herbst-Irmer, R., Spek, A. L., Schneider, T. R. & Sawaya, M. R. (2006). In Crystal Structure Refinement - A Crystallographer's Guide to SHELXL. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C20H24N2O5

  • Mr = 372.41

  • Monoclinic, P 21

  • a = 9.5934 (7) Å

  • b = 9.2266 (7) Å

  • c = 10.3565 (7) Å

  • [beta] = 96.172 (4)°

  • V = 911.39 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 123 K

  • 0.26 × 0.21 × 0.04 mm

Data collection
  • Bruker Nonius X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.996

  • 10366 measured reflections

  • 2111 independent reflections

  • 1943 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.076

  • S = 1.05

  • 2111 reflections

  • 259 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H6O...O7 0.88 (2) 1.70 (2) 2.530 (2) 155 (3)
N8-H8N...O14i 0.87 (2) 2.21 (2) 3.051 (2) 163 (2)
O14-H14O...O16ii 0.85 (2) 2.03 (2) 2.858 (2) 165 (3)
N15-H15N...O7iii 0.86 (2) 2.25 (2) 3.046 (2) 154 (2)
O22-H22O...O16 0.84 (2) 1.95 (2) 2.648 (2) 140 (3)
O22-H22O...O6iv 0.84 (2) 2.19 (2) 2.776 (2) 127 (2)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) [-x, y+{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg, 2012[Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2084 ).


Acknowledgements

The authors thank Dr Volker Huch (Universität des Saarlandes) for the collection of the data set.

References

Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cappillino, P. J., Tarves, P. C., Rowe, G. T., Lewis, A. J., Harvey, M., Rogge, C., Stassinopoulos, A., Lo, W., Armstrong, W. H. & Caradonna, J. P. (2009). Inorg. Chim. Acta, 362, 2136-2150.  [ISI] [CSD] [CrossRef] [ChemPort]
Duhme, A.-K., Dauter, Z., Hider, R. C. & Pohl, S. (1996). Inorg. Chem. 35, 3059-3061.  [CrossRef] [ChemPort] [ISI]
Huang, S.-P., Franz, K. J., Olmstead, M. M. & Fish, R. H. (1995). Inorg. Chem. 34, 2820-2825.  [CrossRef] [ChemPort] [ISI]
Kunze, B., Bedorf, N., Kohl, W., Höfle, G. & Reichenbach, H. (1989). J. Antibiot. 42, 14-17.  [CrossRef] [ChemPort] [PubMed]
Müller, P., Herbst-Irmer, R., Spek, A. L., Schneider, T. R. & Sawaya, M. R. (2006). In Crystal Structure Refinement - A Crystallographer's Guide to SHELXL. Oxford University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoicescu, L., Duhayon, C., Vendier, L., Tesouro-Vallina, A., Costes, J.-P. & Tuchagues, J.-P. (2009). Eur. J. Inorg. Chem. pp. 5483-5493.


Acta Cryst (2013). E69, o223  [ doi:10.1107/S1600536813000354 ]

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