3-Chloro-4-fluoro­anilinium picrate

Sarojini, B.K.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; van Brecht, B.; Betz, R.

doi:10.1107/S1600536813000718

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 14.8
Details

3-Chloro-4-fluoroanilinium picrate

Balladka K. Sarojini,^a Badiadka Narayana,^b Hemmige S. Yathirajan,^c Thomas Gerber,^d Benjamin van Brecht ^d and Richard Betz ^d ^*

^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-HO hydrogen bonds, as well as C-HO contacts, connect the ions into layers parallel to (001).

Related literature

For related structures, see: Jin et al. (2011); Wang (2011); Betz et al. (2011); Dutkiewicz et al. (2011); Jasinski et al. (2010a,b, 2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₆H₆ClF⁺·C₆H₂N₃O₇^-
M_r = 374.67
Triclinic, $[P \overline 1]$
a = 4.4054 (2) Å
b = 11.9881 (5) Å
c = 13.7010 (5) Å
= 90.057 (1)°
= 91.803 (1)°
= 97.743 (1)°
V = 716.62 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.907, T_max = 1.000
12360 measured reflections
3525 independent reflections
2947 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(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
_max = 0.32 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H41O1ⁱ	0.91 (2)	1.85 (2)	2.7324 (17)	165 (2)
N4-H42O12ⁱⁱ	0.89 (2)	2.40 (2)	3.0599 (18)	131.2 (16)
N4-H42O11ⁱⁱ	0.89 (2)	2.60 (2)	3.3425 (17)	141.8 (16)
N4-H43O1	0.96 (2)	1.81 (2)	2.7579 (16)	172.7 (18)
C13-H13O21ⁱⁱⁱ	0.95	2.47	3.3152 (19)	148
C26-H26O32	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o2587-o2588.
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.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Jasinski, J. P., Butcher, R. J., Hakim Al-arique, Q. N. M., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o637-o638.
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010a). Acta Cryst. E66, o1187-o1188.
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Prakash Kamath, K. (2010b). Acta Cryst. E66, o1189-o1190.
Jin, S.-W., Chen, B.-X., Ge, Y.-S., Yin, H.-B. & Fang, Y.-P. (2011). Acta Cryst. E67, o1694.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, W.-Q. (2011). Acta Cryst. E67, o860.

organic compounds