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Volume 69 
Part 2 
Page o240  
February 2013  

Received 3 November 2012
Accepted 8 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 14.8
Details
Open access

3-Chloro-4-fluoroanilinium picrate

aP. A. College of Engineering, Department of Chemistry, Nadupadavu, Mangalore 574 153, India,bMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,cUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and dNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title picrate salt of a dihalogenated aniline derivative, C6H6ClF+·C6H2N3O7-, the intracyclic C-C-C angles in the picrate anion cover a broad range [111.95 (12)-125.38 (13)°], while those in the aromatic cation span a much narrower range [118.25 (14)-122.33 (13)°]. In the crystal, classical N-H...O hydrogen bonds, as well as C-H...O contacts, connect the ions into layers parallel to (001).

Related literature

For related structures, see: Jin et al. (2011[Jin, S.-W., Chen, B.-X., Ge, Y.-S., Yin, H.-B. & Fang, Y.-P. (2011). Acta Cryst. E67, o1694.]); Wang (2011[Wang, W.-Q. (2011). Acta Cryst. E67, o860.]); Betz et al. (2011[Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o2587-o2588.]); Dutkiewicz et al. (2011[Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235.]); Jasinski et al. (2010a[Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010a). Acta Cryst. E66, o1187-o1188.],b[Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010b). Acta Cryst. E66, o1189-o1190.], 2011[Jasinski, J. P., Butcher, R. J., Hakim Al-arique, Q. N. M., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o637-o638.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); 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
  • C6H6ClF+·C6H2N3O7-

  • Mr = 374.67

  • Triclinic, [P \overline 1]

  • a = 4.4054 (2) Å

  • b = 11.9881 (5) Å

  • c = 13.7010 (5) Å

  • [alpha] = 90.057 (1)°

  • [beta] = 91.803 (1)°

  • [gamma] = 97.743 (1)°

  • V = 716.62 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 200 K

  • 0.53 × 0.32 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.907, Tmax = 1.000

  • 12360 measured reflections

  • 3525 independent reflections

  • 2947 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.06

  • 3525 reflections

  • 238 parameters

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H41...O1i 0.91 (2) 1.85 (2) 2.7324 (17) 165 (2)
N4-H42...O12ii 0.89 (2) 2.40 (2) 3.0599 (18) 131.2 (16)
N4-H42...O11ii 0.89 (2) 2.60 (2) 3.3425 (17) 141.8 (16)
N4-H43...O1 0.96 (2) 1.81 (2) 2.7579 (16) 172.7 (18)
C13-H13...O21iii 0.95 2.47 3.3152 (19) 148
C26-H26...O32 0.95 2.49 3.378 (2) 156
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. 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.]) 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 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: BG2490 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o2587-o2588.  [CSD] [CrossRef] [details]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dutkiewicz, G., Samshuddin, S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2011). Acta Cryst. E67, o235.  [CSD] [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jasinski, J. P., Butcher, R. J., Hakim Al-arique, Q. N. M., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o637-o638.  [CSD] [CrossRef] [details]
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010a). Acta Cryst. E66, o1187-o1188.  [CSD] [CrossRef] [details]
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010b). Acta Cryst. E66, o1189-o1190.  [CSD] [CrossRef] [details]
Jin, S.-W., Chen, B.-X., Ge, Y.-S., Yin, H.-B. & Fang, Y.-P. (2011). Acta Cryst. E67, o1694.  [CSD] [CrossRef] [details]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, W.-Q. (2011). Acta Cryst. E67, o860.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o240  [ doi:10.1107/S1600536813000718 ]

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