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Volume 69 
Part 4 
Page o471  
April 2013  

Received 13 February 2013
Accepted 26 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.088
Data-to-parameter ratio = 12.1
Details
Open access

Phenazin-5-ium hydrogen sulfate monohydrate

aDepartment of Physics, Clark University, 950 Main St, Worcester, MA 01610, USA, and bDepartment of Chemistry, Clark University, 950 Main St, Worcester, MA 01610, USA
Correspondence e-mail: mturnbull@clarku.edu

The crystal structure of the title salt, C12H9N2+·HSO4-·H2O, comprises inversion-related pairs of phenazinium ions linked by C-H...N hydrogen bonds. The phenazinium N-H atoms are hydrogen bonded to the bisulfate anions. The bisulfate anions and water molecules are linked by O-H...O hydrogen-bonding interactions into a structural ladder motif parallel to the a axis.

Related literature

For related structures, see: Sieron (2007[Sieron, L. (2007). Acta Cryst. E63, o2508.]) [phenazinium perchlorate]; Plasseraud et al. (2009[Plasseraud, L., Cattey, H., Richard, P. & Ballivet-Tkatchenko, D. (2009). J. Organomet. Chem. 694, 2386-2394.]) [phenazinium trifluoromethanesulfonate]; Braga et al. (2010[Braga, D., Grepioni, F., Maini, L., Mazzeo, P. P. & Rubini, K. (2010). Thermochim. Acta, 507, 1-8.]) [phenazinium chloride and phenazine monohydrate]; G.-X. Zhang et al. (2012[Zhang, N.-Q., Li, P., Dong, J. & Chen, H.-Y. (2012). Acta Cryst. E68, o2101.]) [phenazinium bromide]; N.-Q. Zhang et al. (2012[Zhang, G.-X., Li, P., Dong, J. & Chen, H.-Y. (2012). Acta Cryst. E68, o2204.]) [phenazinium methanesulfonate]. For copper(II) salts of phenazine, see: Schneider et al. (2007[Schneider, R. T., Landee, C. P., Turnbull, M. M., Awwadi, F. F. & Twamley, B. (2007). Polyhedron, 26, 1849-58.]). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9N2+·HSO4-·H2O

  • Mr = 296.30

  • Triclinic, [P \overline 1]

  • a = 5.6565 (4) Å

  • b = 10.4019 (6) Å

  • c = 10.9500 (5) Å

  • [alpha] = 89.693 (4)°

  • [beta] = 87.202 (5)°

  • [gamma] = 76.412 (5)°

  • V = 625.49 (6) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.53 mm-1

  • T = 120 K

  • 0.45 × 0.40 × 0.30 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.786, Tmax = 1.000

  • 3789 measured reflections

  • 2341 independent reflections

  • 2276 reflections with I > 2[sigma](I)

  • Rint = 0.013

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.088

  • S = 1.09

  • 2341 reflections

  • 193 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.86 (2) 1.81 (2) 2.6685 (18) 173.3 (19)
O2-H2...O1S 0.93 (2) 1.59 (2) 2.5223 (16) 177 (2)
O1S-H1A...O4i 0.89 (2) 1.87 (2) 2.7577 (18) 176 (2)
O1S-H1B...O3ii 0.84 (2) 1.90 (2) 2.7405 (18) 173 (2)
C6-H6...N8iii 0.93 2.61 3.538 (2) 172
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+2; (iii) -x-2, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]) and 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: SJ5299 ).


Acknowledgements

We are grateful to Dr Jan Wikaira (University of Canterbury, New Zealand) for assistance with the data collection.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Braga, D., Grepioni, F., Maini, L., Mazzeo, P. P. & Rubini, K. (2010). Thermochim. Acta, 507, 1-8.  [ISI] [CSD] [CrossRef]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Plasseraud, L., Cattey, H., Richard, P. & Ballivet-Tkatchenko, D. (2009). J. Organomet. Chem. 694, 2386-2394.  [CSD] [CrossRef] [ChemPort]
Schneider, R. T., Landee, C. P., Turnbull, M. M., Awwadi, F. F. & Twamley, B. (2007). Polyhedron, 26, 1849-58.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sieron, L. (2007). Acta Cryst. E63, o2508.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, N.-Q., Li, P., Dong, J. & Chen, H.-Y. (2012). Acta Cryst. E68, o2101.  [CSD] [CrossRef] [details]
Zhang, G.-X., Li, P., Dong, J. & Chen, H.-Y. (2012). Acta Cryst. E68, o2204.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o471  [ doi:10.1107/S160053681300562X ]

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