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Volume 69 
Part 10 
Page o1584  
October 2013  

Received 10 September 2013
Accepted 13 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.007 Å
R = 0.054
wR = 0.141
Data-to-parameter ratio = 17.8
Details
Open access

N,N'-Bis(3-bromo-2-hydroxybenzylidene)propane-1,3-diamine

aCollege of Chemistry, Dalian University of Technology, Dalian 116024, People's Republic of China
Correspondence e-mail: xzwang@mail.dlut.edu.cn

In the title compound, C17H16Br2N2O2, the dihedral angle between the benzene rings is 57.7 (3)°. The conformation of the central N-C-C-C-N chain is gauche-anti [torsion angles = -64.2 (4) and -167.8 (4)°]. Two intramolecular O-H...N hydrogen bonds occur. In the crystal, molecules are linked by pairs of C-H...O hydrogen bonds, forming inversion dimers.

Related literature

For a related structure, see: Elerman et al. (1998[Elerman, Y., Elmali, A., Kabak, M. & Svoboda, I. (1998). Acta Cryst. C54, 1701-1703.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16Br2N2O2

  • Mr = 440.14

  • Monoclinic, P 21 /c

  • a = 12.779 (1) Å

  • b = 10.1894 (8) Å

  • c = 14.3953 (12) Å

  • [beta] = 113.744 (2)°

  • V = 1715.8 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.74 mm-1

  • T = 298 K

  • 0.23 × 0.22 × 0.22 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.409, Tmax = 0.422

  • 19018 measured reflections

  • 3728 independent reflections

  • 2669 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.141

  • S = 1.07

  • 3728 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -1.01 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 1.83 2.567 (4) 148
O2-H2...N2 0.82 1.82 2.553 (5) 149
C7-H7...O2i 0.93 2.60 3.490 (5) 161
Symmetry code: (i) -x, -y, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7137 ).


Acknowledgements

The author acknowledges Dalian University of Technology for financial support.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Elerman, Y., Elmali, A., Kabak, M. & Svoboda, I. (1998). Acta Cryst. C54, 1701-1703.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1584  [ doi:10.1107/S1600536813025403 ]

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