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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2909.
Published online 2010 October 23. doi:  10.1107/S1600536810040687
PMCID: PMC3009010

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

Abstract

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—H(...)O inter­action occurs. In the crystal, mol­ecules are linked by weak inter­molecular C—H(...)O, N—H(...)O and C—H(...)F hydrogen bonds, which stabilize the structure.

Related literature

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

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Object name is e-66-o2909-scheme1.jpg

Experimental

Crystal data

  • C19H13F2N3O3
  • M r = 369.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2909-efi1.jpg
  • a = 7.8510 (16) Å
  • b = 8.2720 (17) Å
  • c = 13.835 (3) Å
  • α = 74.75 (3)°
  • β = 85.67 (3)°
  • γ = 70.76 (3)°
  • V = 818.4 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.965, T max = 0.988
  • 3198 measured reflections
  • 2962 independent reflections
  • 1559 reflections with I > 2σ(I)
  • R int = 0.026
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.155
  • S = 1.00
  • 2962 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.18 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040687/pv2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040687/pv2329Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

The crystal structure of the title compound, (I), is presented in this article. In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The phenylaminobenzamide moiety (C1–C13/N1/O1) is essentially planar with maximum deviation of any atom being 0.036 (3) Å for C11 with F2 lying 0.109 (4) Å out of its plane, nitro group (N3/O2/O3) titlted at an angle 9.6 (5)° from its plane and the phenyl ring (C14–C19) inclined at 62.20 (8)° with its plane. In the crystal structure, weak intermolecular C—H···O, N—H···O and C—H···F hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in stabilizing the structure.

Experimental

4-Chloro-3-nitrobenzamide (4.0 g, 0.02 mol) was heated in 4-fluorobenzenamine (10 ml) for 18 h at 403 K. On completion of the reaction (TLC control) was added ethanol (50 ml), at room temperature. The red precipitate thus formed was filtered, washed with cold ethanol (2 × 15 ml), dried over sodium sulfate to provide 5.8 g (79%) of (I) (Schelz & Inst, 1978). The compound (I) was purified by crystallizing from methanol. The crystals of (I) suitable for X-ray diffraction were obstained by slow evaporation of a methanol solution.

Refinement

H atoms were positioned geometrically, with N—H = 0.86 and C—H = 0.93 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C/N).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
Fig. 2.
A packing diagram of (I). The intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C19H13F2N3O3Z = 2
Mr = 369.32F(000) = 380
Triclinic, P1Dx = 1.499 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8510 (16) ÅCell parameters from 25 reflections
b = 8.2720 (17) Åθ = 9–12°
c = 13.835 (3) ŵ = 0.12 mm1
α = 74.75 (3)°T = 293 K
β = 85.67 (3)°Block, colourless
γ = 70.76 (3)°0.30 × 0.20 × 0.10 mm
V = 818.4 (3) Å3

Data collection

Enraf–Nonius CAD-4 diffractometer1559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 25.3°, θmin = 1.5°
ω and 2θ scansh = 0→9
Absorption correction: ψ scan (North et al., 1968)k = −9→9
Tmin = 0.965, Tmax = 0.988l = −16→16
3198 measured reflections3 standard reflections every 200 reflections
2962 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.155w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2962 reflectionsΔρmax = 0.16 e Å3
245 parametersΔρmin = −0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
F10.7511 (3)0.0655 (3)−0.12706 (14)0.0823 (8)
N10.1978 (4)−0.2157 (3)0.58538 (17)0.0468 (7)
H1A0.2383−0.26520.53720.056*
F2−0.0468 (3)−0.6359 (3)0.90592 (15)0.0839 (8)
C10.0848 (6)−0.5958 (5)0.7467 (3)0.0687 (12)
H1C0.0888−0.70830.74430.082*
N20.4401 (4)0.3033 (3)0.20096 (18)0.0511 (8)
H2A0.42320.41410.19340.061*
O10.1462 (4)0.0382 (3)0.63333 (16)0.0645 (8)
C20.1458 (5)−0.4877 (4)0.6679 (3)0.0618 (11)
H2B0.1932−0.52900.61200.074*
O20.3708 (4)0.5620 (3)0.29073 (19)0.0787 (9)
C30.1378 (4)−0.3197 (4)0.6703 (2)0.0424 (8)
N30.3373 (4)0.4670 (4)0.3685 (2)0.0579 (9)
C40.0683 (5)−0.2610 (5)0.7541 (2)0.0515 (9)
H4A0.0612−0.14780.75690.062*
O30.3066 (5)0.5176 (4)0.4448 (2)0.1081 (13)
C50.0093 (5)−0.3689 (5)0.8339 (2)0.0573 (10)
H5A−0.0360−0.33010.89090.069*
C60.0189 (5)−0.5329 (5)0.8276 (3)0.0577 (10)
C70.1996 (4)−0.0465 (4)0.5702 (2)0.0413 (8)
C80.2697 (4)0.0325 (4)0.4724 (2)0.0367 (7)
C90.3296 (4)−0.0471 (4)0.3930 (2)0.0458 (9)
H9A0.3288−0.16160.39960.055*
C100.3893 (4)0.0400 (4)0.3058 (2)0.0463 (9)
H10A0.4292−0.01780.25500.056*
C110.3924 (4)0.2150 (4)0.2904 (2)0.0408 (8)
C120.3347 (4)0.2909 (4)0.3723 (2)0.0411 (8)
C130.2751 (4)0.2014 (4)0.4597 (2)0.0417 (8)
H13A0.23760.25680.51160.050*
C140.5150 (5)0.2322 (4)0.1184 (2)0.0422 (8)
C150.6711 (5)0.0901 (5)0.1283 (2)0.0518 (9)
H15A0.72340.03180.19140.062*
C160.7504 (5)0.0333 (5)0.0459 (3)0.0574 (10)
H16A0.8563−0.06230.05240.069*
C170.6702 (6)0.1204 (5)−0.0458 (3)0.0554 (10)
C180.5142 (5)0.2600 (5)−0.0589 (2)0.0566 (10)
H18A0.46170.3155−0.12210.068*
C190.4358 (5)0.3171 (4)0.0244 (2)0.0495 (9)
H19A0.32980.41260.01730.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.114 (2)0.0861 (17)0.0570 (13)−0.0353 (15)0.0258 (13)−0.0374 (12)
N10.065 (2)0.0442 (16)0.0382 (15)−0.0275 (15)0.0133 (13)−0.0135 (12)
F20.108 (2)0.0535 (14)0.0715 (14)−0.0251 (13)0.0345 (13)0.0043 (11)
C10.094 (3)0.038 (2)0.068 (3)−0.020 (2)0.017 (2)−0.0092 (19)
N20.078 (2)0.0423 (16)0.0389 (16)−0.0291 (16)0.0172 (15)−0.0130 (13)
O10.104 (2)0.0492 (15)0.0487 (14)−0.0345 (15)0.0227 (14)−0.0192 (12)
C20.090 (3)0.044 (2)0.050 (2)−0.024 (2)0.020 (2)−0.0121 (17)
O20.136 (3)0.0554 (16)0.0587 (16)−0.0535 (17)0.0343 (16)−0.0184 (13)
C30.052 (2)0.042 (2)0.0342 (18)−0.0201 (17)0.0066 (16)−0.0069 (15)
N30.089 (3)0.0494 (18)0.0465 (18)−0.0370 (18)0.0176 (17)−0.0165 (16)
C40.063 (3)0.055 (2)0.044 (2)−0.031 (2)0.0094 (18)−0.0129 (17)
O30.225 (4)0.072 (2)0.0626 (18)−0.087 (2)0.050 (2)−0.0403 (16)
C50.068 (3)0.064 (3)0.043 (2)−0.028 (2)0.0144 (18)−0.0145 (18)
C60.062 (3)0.046 (2)0.049 (2)−0.0125 (19)0.0141 (18)0.0043 (17)
C70.045 (2)0.0400 (19)0.0396 (18)−0.0162 (17)0.0017 (16)−0.0091 (16)
C80.040 (2)0.0355 (18)0.0351 (17)−0.0139 (15)−0.0003 (14)−0.0072 (14)
C90.061 (2)0.043 (2)0.0426 (19)−0.0269 (18)0.0063 (17)−0.0134 (15)
C100.060 (2)0.046 (2)0.0427 (19)−0.0260 (18)0.0105 (17)−0.0201 (16)
C110.044 (2)0.0385 (19)0.0412 (19)−0.0149 (16)0.0005 (15)−0.0106 (15)
C120.053 (2)0.0365 (18)0.0384 (18)−0.0195 (17)0.0029 (16)−0.0110 (15)
C130.053 (2)0.0418 (19)0.0339 (17)−0.0186 (17)0.0030 (15)−0.0116 (14)
C140.060 (2)0.0416 (19)0.0353 (18)−0.0296 (19)0.0097 (16)−0.0125 (15)
C150.062 (3)0.050 (2)0.043 (2)−0.020 (2)0.0041 (18)−0.0094 (16)
C160.064 (3)0.049 (2)0.060 (2)−0.0173 (19)0.014 (2)−0.0197 (19)
C170.082 (3)0.060 (2)0.041 (2)−0.040 (2)0.022 (2)−0.0237 (18)
C180.073 (3)0.065 (3)0.039 (2)−0.036 (2)0.0023 (19)−0.0083 (18)
C190.050 (2)0.046 (2)0.049 (2)−0.0173 (18)0.0048 (18)−0.0066 (17)

Geometric parameters (Å, °)

F1—C171.358 (3)C5—H5A0.9300
N1—C71.365 (4)C7—C81.490 (4)
N1—C31.413 (3)C8—C131.376 (4)
N1—H1A0.8600C8—C91.400 (4)
F2—C61.373 (4)C9—C101.369 (4)
C1—C61.354 (5)C9—H9A0.9300
C1—C21.382 (4)C10—C111.415 (4)
C1—H1C0.9300C10—H10A0.9300
N2—C111.357 (4)C11—C121.412 (4)
N2—C141.421 (4)C12—C131.378 (4)
N2—H2A0.8600C13—H13A0.9300
O1—C71.225 (3)C14—C151.376 (4)
C2—C31.379 (4)C14—C191.388 (4)
C2—H2B0.9300C15—C161.375 (4)
O2—N31.222 (3)C15—H15A0.9300
C3—C41.380 (4)C16—C171.366 (5)
N3—O31.214 (3)C16—H16A0.9300
N3—C121.451 (4)C17—C181.363 (5)
C4—C51.381 (4)C18—C191.384 (4)
C4—H4A0.9300C18—H18A0.9300
C5—C61.360 (5)C19—H19A0.9300
C7—N1—C3128.1 (3)C10—C9—C8121.5 (3)
C7—N1—H1A115.9C10—C9—H9A119.3
C3—N1—H1A115.9C8—C9—H9A119.3
C6—C1—C2117.9 (4)C9—C10—C11122.1 (3)
C6—C1—H1C121.0C9—C10—H10A118.9
C2—C1—H1C121.0C11—C10—H10A118.9
C11—N2—C14126.9 (3)N2—C11—C12123.5 (3)
C11—N2—H2A116.6N2—C11—C10121.2 (3)
C14—N2—H2A116.6C12—C11—C10115.2 (3)
C3—C2—C1121.4 (3)C13—C12—C11121.9 (3)
C3—C2—H2B119.3C13—C12—N3116.8 (3)
C1—C2—H2B119.3C11—C12—N3121.2 (3)
C2—C3—C4118.6 (3)C8—C13—C12121.9 (3)
C2—C3—N1117.8 (3)C8—C13—H13A119.0
C4—C3—N1123.6 (3)C12—C13—H13A119.0
O3—N3—O2120.7 (3)C15—C14—C19119.5 (3)
O3—N3—C12118.4 (3)C15—C14—N2121.5 (3)
O2—N3—C12120.9 (3)C19—C14—N2118.8 (3)
C3—C4—C5120.5 (3)C16—C15—C14120.6 (3)
C3—C4—H4A119.7C16—C15—H15A119.7
C5—C4—H4A119.7C14—C15—H15A119.7
C6—C5—C4118.7 (3)C17—C16—C15118.5 (4)
C6—C5—H5A120.7C17—C16—H16A120.7
C4—C5—H5A120.7C15—C16—H16A120.7
C1—C6—C5122.9 (3)F1—C17—C18119.1 (3)
C1—C6—F2119.1 (3)F1—C17—C16118.1 (4)
C5—C6—F2117.9 (3)C18—C17—C16122.8 (3)
O1—C7—N1122.2 (3)C17—C18—C19118.3 (3)
O1—C7—C8120.9 (3)C17—C18—H18A120.8
N1—C7—C8116.9 (3)C19—C18—H18A120.8
C13—C8—C9117.3 (3)C18—C19—C14120.2 (3)
C13—C8—C7115.9 (3)C18—C19—H19A119.9
C9—C8—C7126.8 (3)C14—C19—H19A119.9
C6—C1—C2—C3−0.9 (6)N2—C11—C12—C13175.3 (3)
C1—C2—C3—C40.5 (6)C10—C11—C12—C13−1.7 (5)
C1—C2—C3—N1−178.1 (3)N2—C11—C12—N3−5.3 (5)
C7—N1—C3—C2178.7 (3)C10—C11—C12—N3177.6 (3)
C7—N1—C3—C40.2 (5)O3—N3—C12—C137.8 (5)
C2—C3—C4—C50.4 (5)O2—N3—C12—C13−172.6 (3)
N1—C3—C4—C5178.9 (3)O3—N3—C12—C11−171.5 (4)
C3—C4—C5—C6−0.9 (5)O2—N3—C12—C118.1 (5)
C2—C1—C6—C50.5 (6)C9—C8—C13—C120.8 (5)
C2—C1—C6—F2178.4 (3)C7—C8—C13—C12−179.1 (3)
C4—C5—C6—C10.4 (6)C11—C12—C13—C80.4 (5)
C4—C5—C6—F2−177.5 (3)N3—C12—C13—C8−178.9 (3)
C3—N1—C7—O10.3 (5)C11—N2—C14—C15−56.2 (5)
C3—N1—C7—C8−179.6 (3)C11—N2—C14—C19128.7 (3)
O1—C7—C8—C131.9 (5)C19—C14—C15—C161.0 (5)
N1—C7—C8—C13−178.2 (3)N2—C14—C15—C16−174.0 (3)
O1—C7—C8—C9−178.0 (3)C14—C15—C16—C17−0.4 (5)
N1—C7—C8—C91.9 (5)C15—C16—C17—F1178.9 (3)
C13—C8—C9—C10−0.7 (5)C15—C16—C17—C18−0.6 (5)
C7—C8—C9—C10179.2 (3)F1—C17—C18—C19−178.4 (3)
C8—C9—C10—C11−0.6 (5)C16—C17—C18—C191.0 (5)
C14—N2—C11—C12173.7 (3)C17—C18—C19—C14−0.4 (5)
C14—N2—C11—C10−9.4 (5)C15—C14—C19—C18−0.5 (5)
C9—C10—C11—N2−175.3 (3)N2—C14—C19—C18174.6 (3)
C9—C10—C11—C121.8 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.862.373.185 (4)158
N2—H2A···O20.861.982.636 (4)132
N2—H2A···N30.862.582.917 (4)105
C2—H2B···O3i0.932.403.240 (5)151
C4—H4A···O10.932.202.821 (4)123
C10—H10A···F1ii0.932.533.205 (4)130
C13—H13A···O10.932.392.728 (4)102
C13—H13A···O30.932.332.661 (5)100
C15—H15A···O1iii0.932.553.454 (4)164
C16—H16A···F2iv0.932.393.272 (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.

Footnotes

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

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. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography