4-(4-Fluoro­anilino)-N-(4-fluoro­phen­yl)-3-nitro­benzamide

Wang, Y.; Fan, K.; Li, C.; Ge, C.

doi:10.1107/S1600536810040687

Volume 66
Part 11
Page o2909
November 2010

Received 16 September 2010
Accepted 11 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.155
Data-to-parameter ratio = 12.1
Details

4-(4-Fluoroanilino)-N-(4-fluorophenyl)-3-nitrobenzamide

Yong Wang,^a ^* Kaiqing Fan,^b Chenghong Li ^a and Changhua Ge ^a

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China, and ^bAgronomy Department, Jiangsu Polytechnic College of Agriculture and Forestry, Jurong 212400 Jiangsu, People's Republic of China
Correspondence e-mail: yutaitang@hotmail.com

In the title compound, C₁₉H₁₃F₂N₃O₃, the anilinobenzamide unit is essentially planar, with a maximum deviation of 0.036 (3) Å. The nitro group and the benzene ring form dihedral angles of 9.6 (5)and 62.20 (8)°, respectively, with the anilinobenzamide unit. An intramolecular N-HO interaction occurs. In the crystal, molecules are linked by weak intermolecular C-HO, N-HO and C-HF hydrogen bonds, which stabilize the structure.

Related literature

For comparison of bond lengths, see: Allen et al. (1987). For the synthetic procedure, see: Schelz & Inst (1978).

Experimental

Crystal data

C₁₉H₁₃F₂N₃O₃
M_r = 369.32
Triclinic, $[P \overline 1]$
a = 7.8510 (16) Å
b = 8.2720 (17) Å
c = 13.835 (3) Å
= 74.75 (3)°
= 85.67 (3)°
= 70.76 (3)°
V = 818.4 (3) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.965, T_max = 0.988
3198 measured reflections
2962 independent reflections
1559 reflections with I > 2(I)
R_int = 0.026
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.155
S = 1.00
2962 reflections
245 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO3ⁱ	0.86	2.37	3.185 (4)	158
N2-H2AO2	0.86	1.98	2.636 (4)	132
C2-H2BO3ⁱ	0.93	2.40	3.240 (5)	151
C10-H10AF1ⁱⁱ	0.93	2.53	3.205 (4)	130
C15-H15AO1ⁱⁱⁱ	0.93	2.55	3.454 (4)	164
C16-H16AF2^iv	0.93	2.39	3.272 (5)	158
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) -x+1, -y, -z+1; (iv) -x+1, -y-1, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1994); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2329 ).

Acknowledgements

The authors thank Dr Shan Liu of Nanjing University of Technology for useful discussions and the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Schelz, D. & Inst, F. (1978). Helv. Chim. Acta, 61, 2452-2462.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds