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Volume 69 
Part 9 
Page o1455  
September 2013  

Received 8 July 2013
Accepted 3 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.126
Data-to-parameter ratio = 16.5
Details
Open access

Bis(2-hydroxyethyl)ammonium picrate

aDepartment of Physics, Anna University, Chennai 600 025, India
Correspondence e-mail: krgkrishnan@annauniv.edu

The asymmetric unit of the title salt, C4H12NO2+·C6H2N3O7-, contain two bis(2-hydroxyethyl)ammonium cations and two picrate anions. An intramolecular N-H...O hydrogen bond occurs in each cation. In the crystal, molecules are linked via O-H...O and N-H...O hydrogen bonds, which generate two R21(6), an R22(10) and an R22(13) graph-set ring motifs. There are also a number of C-H...O hydrogen bonds present. The sum of these interactions leads to the formation a three-dimensional structure.

Related literature

For general background to picrate complexes, see: In et al. (1997[In, Y., Nagata, H., Doi, M., Ishida, T. & Wakahara, A. (1997). Acta Cryst. C53, 367-369.]); Zaderenko et al. 1997[Zaderenko, P., Gil, M. S., López, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997). Acta Cryst. B53, 961-967.]); Ashwell et al. (1995[Ashwell, G. J., Jefferies, G., Hamilton, D. G., Lynch, D. E., Roberts, M. P. S., Bahra, G. S. & Brown, C. R. (1995). Nature (London), 375, 385-388.]); Owen & White (1976[Owen, J. R. & White, E. A. D. (1976). J. Mater. Sci. 11, 2165-2169.]); Shakir et al. (2009[Shakir, M., Kushwaha, S. K., Maurya, K. K., Arora, M. & Bhagavannarayana, G. (2009). J. Cryst. Growth, 311, 3871-3875.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C4H12NO2+·C6H2N3O7-

  • Mr = 334.25

  • Monoclinic, P 21 /c

  • a = 24.9396 (6) Å

  • b = 6.9158 (2) Å

  • c = 16.2974 (5) Å

  • [beta] = 94.608 (1)°

  • V = 2801.85 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.882, Tmax = 0.966

  • 31581 measured reflections

  • 7194 independent reflections

  • 5200 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.126

  • S = 1.03

  • 7194 reflections

  • 436 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N7-H7A...O15 0.91 (1) 2.48 (2) 2.8235 (19) 103 (1)
N7-H7A...O17i 0.91 (1) 2.43 (2) 2.9853 (18) 120 (1)
N7-H7A...O18ii 0.91 (1) 2.21 (1) 2.9272 (18) 136 (2)
N7-H7B...O8i 0.91 (2) 1.97 (2) 2.8359 (18) 157 (2)
N7-H7B...O14i 0.91 (2) 2.36 (2) 2.969 (2) 125 (1)
N8-H8A...O15iii 0.91 (2) 2.05 (2) 2.9076 (18) 157 (1)
N8-H8B...O18 0.91 (2) 2.56 (2) 2.898 (2) 103 (1)
N8-H8B...O16iv 0.91 (2) 1.96 (2) 2.8523 (18) 170 (2)
O15-H15...O1 0.82 2.12 2.7891 (16) 139
O15-H15...O2 0.82 2.41 3.138 (2) 149
O16-H16...O17i 0.82 2.24 2.9822 (18) 150
O17-H17...O8 0.82 2.00 2.7323 (14) 148
O17-H17...O9 0.82 2.27 2.9079 (19) 134
O18-H18...O1iv 0.82 1.96 2.7453 (18) 161
C3-H3...O7iv 0.93 2.59 3.502 (2) 167
C9-H9...O13i 0.93 2.50 3.425 (2) 176
C17-H17A...O12v 0.97 2.50 3.359 (2) 147
C19-H19A...O7iii 0.97 2.45 3.319 (3) 148
C19-H19B...O5vi 0.97 2.44 3.224 (2) 138
C21-H21B...O1iii 0.97 2.33 3.195 (2) 148
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) -x, -y+1, -z+1; (vi) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2621 ).


Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the data collection and acknowledge the Council of Scientific and Industrial research (CSIR) Government of India, for funding this project [No. 03 (115)/10/EMR-II].

References

Ashwell, G. J., Jefferies, G., Hamilton, D. G., Lynch, D. E., Roberts, M. P. S., Bahra, G. S. & Brown, C. R. (1995). Nature (London), 375, 385-388.  [CrossRef] [ChemPort] [ISI]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
In, Y., Nagata, H., Doi, M., Ishida, T. & Wakahara, A. (1997). Acta Cryst. C53, 367-369.  [CSD] [CrossRef] [details]
Owen, J. R. & White, E. A. D. (1976). J. Mater. Sci. 11, 2165-2169.  [CrossRef] [ChemPort] [ISI]
Shakir, M., Kushwaha, S. K., Maurya, K. K., Arora, M. & Bhagavannarayana, G. (2009). J. Cryst. Growth, 311, 3871-3875.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Zaderenko, P., Gil, M. S., López, P., Ballesteros, P., Fonseca, I. & Albert, A. (1997). Acta Cryst. B53, 961-967.  [ISI] [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1455  [ doi:10.1107/S1600536813021697 ]

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