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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1757.
Published online 2009 July 4. doi:  10.1107/S1600536809024787
PMCID: PMC2977102

2-Chloro-4-fluoro-N-phenyl­benzamide

Abstract

In the title compound, C13H9ClFNO, the dihedral angle between the two aromatic rings is 13.6 (2)°. In the crystal, the mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds into chains extending along the c-axis direction.

Related literature

For the chemical and pharmacological properties of amides, see: Arrizabalaga et al. (1984 [triangle]); Šladowska et al. (1999 [triangle]).

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Object name is e-65-o1757-scheme1.jpg

Experimental

Crystal data

  • C13H9ClFNO
  • M r = 249.66
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1757-efi1.jpg
  • a = 22.262 (3) Å
  • b = 5.6452 (6) Å
  • c = 9.6743 (12) Å
  • β = 105.832 (2)°
  • V = 1169.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 298 K
  • 0.45 × 0.40 × 0.27 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.869, T max = 0.919
  • 2887 measured reflections
  • 1671 independent reflections
  • 1470 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.079
  • S = 1.04
  • 1671 reflections
  • 154 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.12 e Å−3
  • Absolute structure: Flack, (1983 [triangle]), 637 Friedel pairs
  • Flack parameter: 0.04 (7)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024787/si2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024787/si2182Isup2.hkl

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

Acknowledgments

The authors thank the Science Foundation of Hunan Institute of Engineering, China for support.

supplementary crystallographic information

Comment

The chemical and pharmacological properties of acid amides have been investigated extensively, owing to their chelating ability with metal ions and to their potentially beneficial chemical and biological activties (Arrizabalaga et al., 1984; Šladowska et al., 1999). As part of our studies on the synthesis and characterization of related compounds, we report here the synthesis and crystal structure of 2-chloro-4-fluoro-N-phenylbenzamide. The C=O bond length is 1.224 (3) Å, indicating that the molecule is in the keto form (Fig. 1). In the crystal structure, the molecules are linked by intermolecular N—H···O hydrogen bonds into chains, which extend along the c direction (Table 1 and Fig. 2)

Experimental

A solution of 2-chloro-4-fluorobenzoyl chloride (10 mmol) in 50 ml toluene was added to a solution of aniline (10 mmol) in 10 ml toluene. The reaction mixture was refluxed for 1 h with stirring then the resulting white precipitate was obtained by filtration, washed several times with ethanol and dried in vacuo (yield 90%). Elemental analysis calculated: C, 62.54; H, 3.63; N, 5.61; found: C, 62.51; H, 3.62; N, 5.59. Crystals were obtained by slow evaporation of a solution in methanol after one week.

Refinement

H atoms were placed geometrically and refined using a riding model, with C—H = 0.93Å and N—H = 0.86 Å, respectively. Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Crystal packing of the title compound, showing the hydrogen bonds as dashed lines.

Crystal data

C13H9ClFNOF(000) = 512
Mr = 249.66Dx = 1.418 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 22.262 (3) ÅCell parameters from 1638 reflections
b = 5.6452 (6) Åθ = 2.9–27.0°
c = 9.6743 (12) ŵ = 0.32 mm1
β = 105.832 (2)°T = 298 K
V = 1169.7 (2) Å3Block, colorless
Z = 40.45 × 0.40 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer1671 independent reflections
Radiation source: fine-focus sealed tube1470 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −24→26
Tmin = 0.869, Tmax = 0.919k = −6→5
2887 measured reflectionsl = −11→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.079w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1416P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1671 reflectionsΔρmax = 0.21 e Å3
154 parametersΔρmin = −0.12 e Å3
2 restraintsAbsolute structure: Flack, (1983), 637 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (7)

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
Cl10.25827 (4)0.57325 (11)0.03581 (7)0.0567 (2)
F10.19086 (10)−0.1122 (4)0.2865 (2)0.0839 (7)
N10.42846 (11)0.5122 (4)0.3097 (2)0.0439 (5)
H10.42000.49440.39070.053*
O10.39721 (10)0.4168 (4)0.0742 (2)0.0619 (6)
C10.38996 (13)0.4115 (4)0.1951 (3)0.0407 (6)
C20.33604 (12)0.2803 (4)0.2241 (2)0.0362 (6)
C30.27498 (13)0.3337 (4)0.1537 (3)0.0392 (6)
C40.22559 (14)0.2060 (5)0.1747 (3)0.0479 (7)
H40.18450.24580.12810.057*
C50.23956 (15)0.0173 (6)0.2675 (3)0.0538 (8)
C60.29854 (16)−0.0470 (5)0.3395 (3)0.0513 (8)
H60.3061−0.17720.40080.062*
C70.34669 (13)0.0887 (5)0.3182 (3)0.0457 (7)
H70.38750.05100.36810.055*
C80.48249 (13)0.6470 (5)0.3095 (3)0.0428 (7)
C90.47880 (18)0.8278 (6)0.2111 (4)0.0632 (8)
H90.44150.85930.14220.076*
C100.5315 (2)0.9607 (7)0.2168 (5)0.0802 (12)
H100.52961.08100.15010.096*
C110.5862 (2)0.9185 (6)0.3187 (5)0.0805 (12)
H110.62121.01070.32200.097*
C120.58956 (18)0.7403 (7)0.4161 (5)0.0810 (10)
H120.62690.71020.48550.097*
C130.53723 (17)0.6047 (6)0.4110 (4)0.0637 (9)
H130.53950.48380.47750.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0651 (5)0.0510 (4)0.0528 (5)0.0117 (4)0.0138 (3)0.0092 (4)
F10.0792 (15)0.0871 (14)0.0939 (17)−0.0334 (11)0.0379 (13)0.0012 (12)
N10.0456 (13)0.0597 (13)0.0304 (13)−0.0075 (11)0.0170 (10)−0.0029 (10)
O10.0661 (15)0.0934 (16)0.0314 (11)−0.0216 (11)0.0221 (10)−0.0078 (10)
C10.0450 (15)0.0521 (15)0.0278 (15)0.0011 (13)0.0145 (12)0.0014 (12)
C20.0434 (15)0.0422 (14)0.0235 (13)−0.0018 (12)0.0101 (11)−0.0035 (10)
C30.0473 (16)0.0376 (13)0.0340 (15)0.0002 (11)0.0133 (13)−0.0045 (11)
C40.0416 (16)0.0548 (16)0.0473 (17)−0.0005 (13)0.0122 (13)−0.0097 (14)
C50.060 (2)0.0530 (17)0.056 (2)−0.0156 (18)0.0290 (18)−0.0052 (14)
C60.070 (2)0.0450 (17)0.0436 (18)−0.0034 (14)0.0226 (16)0.0029 (13)
C70.0496 (18)0.0528 (16)0.0337 (15)0.0032 (13)0.0097 (14)−0.0016 (13)
C80.0431 (18)0.0492 (15)0.0410 (16)−0.0041 (13)0.0199 (14)−0.0049 (12)
C90.065 (2)0.0698 (19)0.057 (2)−0.0049 (17)0.0210 (17)0.0119 (17)
C100.088 (3)0.072 (2)0.090 (3)−0.018 (2)0.042 (3)0.014 (2)
C110.062 (3)0.084 (3)0.102 (3)−0.021 (2)0.034 (3)−0.005 (2)
C120.048 (2)0.088 (3)0.103 (3)−0.0086 (18)0.0121 (18)0.002 (2)
C130.056 (2)0.071 (2)0.062 (2)−0.0065 (17)0.0130 (17)0.0067 (16)

Geometric parameters (Å, °)

Cl1—C31.743 (3)C6—H60.9300
F1—C51.361 (4)C7—H70.9300
N1—C11.330 (4)C8—C131.362 (5)
N1—C81.424 (3)C8—C91.382 (4)
N1—H10.8600C9—C101.381 (5)
O1—C11.224 (3)C9—H90.9300
C1—C21.500 (4)C10—C111.363 (6)
C2—C31.377 (4)C10—H100.9300
C2—C71.392 (4)C11—C121.366 (6)
C3—C41.375 (4)C11—H110.9300
C4—C51.373 (4)C12—C131.383 (5)
C4—H40.9300C12—H120.9300
C5—C61.357 (5)C13—H130.9300
C6—C71.378 (4)
C1—N1—C8125.4 (2)C6—C7—C2122.0 (3)
C1—N1—H1117.3C6—C7—H7119.0
C8—N1—H1117.3C2—C7—H7119.0
O1—C1—N1124.3 (3)C13—C8—C9120.0 (3)
O1—C1—C2120.8 (2)C13—C8—N1119.7 (3)
N1—C1—C2114.9 (2)C9—C8—N1120.3 (3)
C3—C2—C7117.5 (2)C10—C9—C8118.9 (3)
C3—C2—C1122.1 (2)C10—C9—H9120.5
C7—C2—C1120.2 (2)C8—C9—H9120.5
C4—C3—C2122.2 (2)C11—C10—C9121.1 (3)
C4—C3—Cl1117.8 (2)C11—C10—H10119.5
C2—C3—Cl1119.92 (19)C9—C10—H10119.5
C5—C4—C3117.1 (3)C10—C11—C12119.8 (3)
C5—C4—H4121.5C10—C11—H11120.1
C3—C4—H4121.5C12—C11—H11120.1
C6—C5—F1118.8 (3)C11—C12—C13119.8 (4)
C6—C5—C4123.9 (3)C11—C12—H12120.1
F1—C5—C4117.3 (3)C13—C12—H12120.1
C5—C6—C7117.2 (3)C8—C13—C12120.5 (3)
C5—C6—H6121.4C8—C13—H13119.7
C7—C6—H6121.4C12—C13—H13119.7
C8—N1—C1—O12.1 (4)C4—C5—C6—C70.7 (4)
C8—N1—C1—C2−179.5 (2)C5—C6—C7—C2−1.6 (4)
O1—C1—C2—C3−58.5 (3)C3—C2—C7—C61.1 (4)
N1—C1—C2—C3123.1 (3)C1—C2—C7—C6−175.2 (2)
O1—C1—C2—C7117.5 (3)C1—N1—C8—C13−133.3 (3)
N1—C1—C2—C7−60.9 (3)C1—N1—C8—C949.8 (4)
C7—C2—C3—C40.5 (4)C13—C8—C9—C100.9 (5)
C1—C2—C3—C4176.6 (2)N1—C8—C9—C10177.8 (3)
C7—C2—C3—Cl1179.33 (19)C8—C9—C10—C11−1.0 (6)
C1—C2—C3—Cl1−4.5 (3)C9—C10—C11—C120.8 (6)
C2—C3—C4—C5−1.4 (4)C10—C11—C12—C13−0.4 (6)
Cl1—C3—C4—C5179.8 (2)C9—C8—C13—C12−0.5 (5)
C3—C4—C5—C60.7 (4)N1—C8—C13—C12−177.4 (3)
C3—C4—C5—F1−178.8 (2)C11—C12—C13—C80.2 (6)
F1—C5—C6—C7−179.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.042.857 (3)159

Symmetry codes: (i) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2182).

References

  • Arrizabalaga, P., Castan, P. & Laurent, J. P. (1984). J. Am. Chem. Soc.106, 4814-4818.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Šladowska, H., Sieklucka-Dziuba, M., Rajtar, G., Sodowski, M. & Kleinrok, Z. (1999). Farmaco, 54, 773–779. [PubMed]

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