organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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N′-(2-Fluoro­benzo­yl)benzohydrazide

aInstitute of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland, bDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and cDepartment of Environmental Sciences, International Islamic University, Islamabad 45320, Pakistan
*Correspondence e-mail: mzareef71@yahoo.com

(Received 1 April 2008; accepted 14 May 2008; online 21 May 2008)

In the crystal structure of the title compound, C14H11FN2O2, the molecule is centrosymmetric. The F atom is disordered over four positions, on the two ortho positions of each ring, with occupancies of 0.287:0.213 (5). In the crystal structure, mol­ecules are linked by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Silva et al. (2006[Silva, J. F. P., Ellena, J., Ferreira, M. de L., Mascarenhas, Y. P., de Souza, M. V. N., Vasconcelos, T. R. A., Wardell, J. L. & Wardell, S. M. S. V. (2006). J. Mol. Struct. 788, 63-71.]); Chopra et al. (2006[Chopra, D., Mohan, T. P. & Vishalakshi, B. (2006). Acta Cryst. E62, o3085-o3086.]); de Souza et al. (2007[Souza, M. V. N. de, Wardell, S. M. S. V., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. E63, o230-o232.]); Ahmad et al. (2001[Ahmad, R., Iqbal, R., Akhtar, R. H., Haq, Z. U., Duddeck, H., Stefaniak, L. & Sitkowski, J. (2001). Nucleosides Nucleotides Nucleic Acids, 20, 1671-1682.]); Al-Soud, et al. (2004[Al-Soud, Y. A., Al-Deeri, M. N. & Al-Mosoudi, N. A. (2004). Farmaco, 59, 775-783.]); Al-Talib et al. (1990[Al-Talib, M., Tastoush, H. & Odeh, N. (1990). Synth. Commun. 20, 1811-1814.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]); Yousif et al. (1986[Yousif, M. Y., Ismail, A. M., Elman, A. A. & El-Kerdawy, M. M. (1986). J. Chem. Soc. Pak. 8, 183-187.]); Zareef & Iqbal (2007[Zareef, M. & Iqbal, R. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 281-298.]); Zheng et al. (2003[Zheng, X., Li, Z., Wang, Y., Chen, W., Huang, Q., Liu, C. & Song, G. (2003). J. Fluorine Chem. 117, 163-169.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11FN2O2

  • Mr = 258.25

  • Monoclinic, P 21 /c

  • a = 4.7698 (10) Å

  • b = 5.2435 (10) Å

  • c = 23.913 (5) Å

  • β = 100.89 (3)°

  • V = 587.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 90.0 (1) K

  • 0.25 × 0.20 × 0.10 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: none

  • 3819 measured reflections

  • 1205 independent reflections

  • 1060 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.094

  • S = 1.07

  • 1205 reflections

  • 118 parameters

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

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3i 0.84 (2) 2.05 (2) 2.8549 (16) 160.4 (16)
N1—H1⋯O3ii 0.84 (2) 2.325 (16) 2.6302 (14) 101.8 (14)
C8—H8⋯O3iii 0.945 (17) 2.416 (16) 3.2687 (17) 150.0 (12)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2002[Oxford Diffraction (2002). CrysAlis CCD. Oxford Diffraction, Wrocław, Poland.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis RED. Oxford Diffraction, Wrocław, Poland.]); data reduction: CrysAlis RED; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

N,N'-Diacylhydrazines are very important intermediates especially for the synthesis of various biological active five member heterocyclic compounds such as 2,5-disubstituted-1,3,4-oxadiazoles (Zheng et al., 2003; Al-Talib et al., 1990) and 5-substituted-2-mercapto-1,3,4-oxadiazoles (Yousif et al., 1986; Ahmad et al., 2001; Al-Soud et al., 2004; El-Emam et al., 2004). In view of the versatility of these compounds, we have synthesized the title compound, (I), using a literature method (Zareef et al., 2007) and reported its crystal structure. The geometry of (I) is normal and (Table 1) compares well with those found in other crystal structures (Silva et al., 2006; Chopra et al., 2006; Souza et al., 2007). The title molecule, C14H11N2O2F, is non-planar. The dihedral angle between the benzene rings and CONHNHCO group is 34.5 (5) °. The disorder of the title molecule is realised by the presents of two positions for F atom with occupancy factors of 0.3 for F10 and 0.2 for F10'. The molecules are linked into a three-dimensional framework by a combination of two N–H···O and one weak C–H···O hydrogen bonds.

Related literature top

For related literature, see: Silva et al. (2006); Chopra et al. (2006); de Souza et al. (2007); Ahmad et al. (2001); Al-Soud, Al-Deeri & Al-Mosoudi (2004); Al-Talib, Tastoush & Odeh (1990); El-Emam, Al–Deeb, Al–Omar & Lehmann (2004); Yousif et al. (1986); Zareef & Iqbal (2007); Zheng et al. (2003).

Experimental top

For the synthesis of title compound (I), benzoyl chloride (5.1 mmol) was added in portions to a suspension of 2-fluorobenzoic hydrazide (5.0 mmol) in dry acetonitrile (50 ml), and the reaction mixture was stirred for 9 h at 296 K. Then, the resulting mixture was concentrated, and the solid product filtered and recrystallized from aqueous ethanol to afford the title compound (yield; 87%). Suitable crystals were grown from a solution of (I) in ethanol by slow evaporation at room temperature.

Refinement top

The occupancy factors for the disordered fluorine and hydrogen (H5 and H9) atoms were refined using free variables. The H5 nad H9 were included in the refinement at geometrically idealized positions with C-H distances 0.96 A and their parameters are not refinement. The remaining H atoms were located in a difference map and freely refined.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title molecule with anisotropic displacement parameters shown at the 50% probability level. [Symmetry code: (i) -x, -y, -z].
[Figure 2] Fig. 2. The packing diagram of the title compound. Dashed lines indicate hydrogen bonds.
N'-(2-Fluorobenzoyl)benzohydrazide top
Crystal data top
C14H11FN2O2F(000) = 268
Mr = 258.25Dx = 1.460 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1205 reflections
a = 4.7698 (10) Åθ = 3.5–26.5°
b = 5.2435 (10) ŵ = 0.11 mm1
c = 23.913 (5) ÅT = 90 K
β = 100.89 (3)°Plate, colourless
V = 587.3 (2) Å30.25 × 0.20 × 0.10 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1060 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 26.5°, θmin = 3.5°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1h = 55
ω scansk = 46
3819 measured reflectionsl = 3030
1205 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0555P)2 + 1.578P]
where P = (Fo2 + 2Fc2)/3
1205 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C14H11FN2O2V = 587.3 (2) Å3
Mr = 258.25Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.7698 (10) ŵ = 0.11 mm1
b = 5.2435 (10) ÅT = 90 K
c = 23.913 (5) Å0.25 × 0.20 × 0.10 mm
β = 100.89 (3)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1060 reflections with I > 2σ(I)
3819 measured reflectionsRint = 0.044
1205 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.28 e Å3
1205 reflectionsΔρmin = 0.28 e Å3
118 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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) top
xyzUiso*/UeqOcc. (<1)
N10.4363 (2)0.5857 (2)0.47949 (4)0.0183 (3)
C20.5853 (2)0.6622 (2)0.44055 (5)0.0166 (3)
O30.83154 (17)0.58840 (19)0.44180 (4)0.0255 (3)
C40.4404 (2)0.8420 (2)0.39624 (5)0.0163 (3)
C50.5167 (3)0.8362 (2)0.34288 (5)0.0193 (3)
H50.65610.71490.33560.023*0.77 (6)
C60.3958 (3)1.0022 (3)0.30033 (5)0.0228 (3)
C70.1997 (3)1.1812 (2)0.31099 (5)0.0237 (3)
C80.1226 (3)1.1921 (2)0.36398 (6)0.0235 (3)
C90.2420 (2)1.0224 (2)0.40602 (5)0.0189 (3)
H90.18621.02900.44250.023*0.73 (6)
F100.1593 (5)1.0332 (5)0.45796 (13)0.0224 (10)0.287 (5)
F10'0.6956 (8)0.6688 (8)0.33028 (14)0.0240 (13)0.213 (5)
H10.258 (4)0.605 (3)0.4759 (7)0.037 (5)*
H60.456 (3)0.995 (3)0.2630 (7)0.030 (4)*
H70.114 (3)1.296 (3)0.2808 (7)0.034 (4)*
H80.007 (3)1.315 (3)0.3730 (6)0.030 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0108 (5)0.0275 (6)0.0168 (5)0.0041 (4)0.0032 (4)0.0053 (4)
C20.0118 (6)0.0233 (6)0.0149 (5)0.0003 (4)0.0029 (4)0.0014 (4)
O30.0128 (5)0.0416 (6)0.0234 (5)0.0072 (4)0.0066 (3)0.0104 (4)
C40.0112 (5)0.0201 (6)0.0170 (6)0.0023 (4)0.0011 (4)0.0004 (4)
C50.0167 (6)0.0225 (6)0.0185 (6)0.0016 (5)0.0030 (5)0.0002 (5)
C60.0233 (7)0.0274 (7)0.0171 (6)0.0013 (5)0.0028 (5)0.0017 (5)
C70.0205 (6)0.0231 (6)0.0251 (6)0.0002 (5)0.0019 (5)0.0073 (5)
C80.0192 (6)0.0191 (6)0.0324 (7)0.0032 (5)0.0052 (5)0.0007 (5)
C90.0171 (6)0.0202 (6)0.0200 (6)0.0013 (5)0.0050 (5)0.0017 (4)
F100.0267 (15)0.0234 (14)0.0195 (16)0.0052 (10)0.0104 (10)0.0014 (10)
F10'0.026 (2)0.029 (2)0.0184 (18)0.0116 (15)0.0068 (14)0.0018 (13)
Geometric parameters (Å, º) top
N1—C21.3354 (16)C6—C71.3824 (19)
N1—N1i1.384 (2)C6—H60.989 (15)
N1—H10.84 (2)C7—C81.3856 (19)
C2—O31.2315 (14)C7—H70.971 (17)
C2—C41.4875 (16)C8—C91.3822 (18)
C4—C91.3890 (17)C8—H80.945 (17)
C4—C51.3916 (17)C9—F101.373 (4)
C5—F10'1.299 (5)C9—H90.9600
C5—C61.3797 (18)F10—H90.4136
C5—H50.9600F10'—H50.3448
C2—N1—N1i117.97 (12)C5—C6—C7119.69 (12)
C2—N1—H1123.5 (11)C5—C6—H6119.3 (10)
N1i—N1—H1116.7 (12)C7—C6—H6121.0 (10)
O3—C2—N1121.31 (11)C6—C7—C8120.16 (12)
O3—C2—C4121.94 (11)C6—C7—H7119.4 (10)
N1—C2—C4116.75 (10)C8—C7—H7120.4 (10)
C9—C4—C5118.28 (11)C9—C8—C7119.64 (12)
C9—C4—C2123.46 (11)C9—C8—H8118.0 (9)
C5—C4—C2118.20 (10)C7—C8—H8122.3 (9)
F10'—C5—C6117.16 (18)F10—C9—C8118.83 (14)
F10'—C5—C4121.64 (17)F10—C9—C4120.10 (14)
C6—C5—C4121.15 (11)C8—C9—C4121.07 (11)
C6—C5—H5119.4C8—C9—H9119.4
C4—C5—H5119.5C4—C9—H9119.5
N1i—N1—C2—O31.9 (2)F10'—C5—C6—C7178.7 (2)
N1i—N1—C2—C4178.67 (12)C4—C5—C6—C71.29 (19)
O3—C2—C4—C9147.25 (13)C5—C6—C7—C80.64 (19)
N1—C2—C4—C932.16 (16)C6—C7—C8—C90.29 (19)
O3—C2—C4—C529.97 (17)C7—C8—C9—F10178.88 (16)
N1—C2—C4—C5150.62 (11)C7—C8—C9—C40.61 (19)
C9—C4—C5—F10'178.3 (2)C5—C4—C9—F10179.49 (16)
C2—C4—C5—F10'4.3 (3)C2—C4—C9—F103.3 (2)
C9—C4—C5—C60.97 (18)C5—C4—C9—C80.01 (18)
C2—C4—C5—C6178.33 (11)C2—C4—C9—C8177.23 (11)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3ii0.84 (2)2.05 (2)2.8549 (16)160.4 (16)
N1—H1···O3i0.84 (2)2.325 (16)2.6302 (14)101.8 (14)
C8—H8···O3iii0.945 (17)2.416 (16)3.2687 (17)150.0 (12)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H11FN2O2
Mr258.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)90
a, b, c (Å)4.7698 (10), 5.2435 (10), 23.913 (5)
β (°) 100.89 (3)
V3)587.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.25 × 0.20 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3819, 1205, 1060
Rint0.044
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.094, 1.07
No. of reflections1205
No. of parameters118
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.28

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.84 (2)2.05 (2)2.8549 (16)160.4 (16)
N1—H1···O3ii0.84 (2)2.325 (16)2.6302 (14)101.8 (14)
C8—H8···O3iii0.945 (17)2.416 (16)3.2687 (17)150.0 (12)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x1, y+1, z.
 

Acknowledgements

The authors are grateful to the late Professor Dr Rashid Iqbal for his great contribution to this research project.

References

First citationAhmad, R., Iqbal, R., Akhtar, R. H., Haq, Z. U., Duddeck, H., Stefaniak, L. & Sitkowski, J. (2001). Nucleosides Nucleotides Nucleic Acids, 20, 1671–1682.  CrossRef PubMed CAS
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First citationZheng, X., Li, Z., Wang, Y., Chen, W., Huang, Q., Liu, C. & Song, G. (2003). J. Fluorine Chem. 117, 163–169.  Web of Science CrossRef

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