In the crystal structure of the title compound, C
14H
11FN
2O
2, 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.
Supporting information
CCDC reference: 691133
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean
(C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.095
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
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.
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).
N'-(2-Fluorobenzoyl)benzohydrazide
top
Crystal data top
C14H11FN2O2 | F(000) = 268 |
Mr = 258.25 | Dx = 1.460 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1205 reflections |
a = 4.7698 (10) Å | θ = 3.5–26.5° |
b = 5.2435 (10) Å | µ = 0.11 mm−1 |
c = 23.913 (5) Å | T = 90 K |
β = 100.89 (3)° | Plate, colourless |
V = 587.3 (2) Å3 | 0.25 × 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 tube | Rint = 0.044 |
Graphite monochromator | θmax = 26.5°, θmin = 3.5° |
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1 | h = −5→5 |
ω scans | k = −4→6 |
3819 measured reflections | l = −30→30 |
1205 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H 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 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C14H11FN2O2 | V = 587.3 (2) Å3 |
Mr = 258.25 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.7698 (10) Å | µ = 0.11 mm−1 |
b = 5.2435 (10) Å | T = 90 K |
c = 23.913 (5) Å | 0.25 × 0.20 × 0.10 mm |
β = 100.89 (3)° | |
Data collection top
Oxford Diffraction Xcalibur diffractometer | 1060 reflections with I > 2σ(I) |
3819 measured reflections | Rint = 0.044 |
1205 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.28 e Å−3 |
1205 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.4363 (2) | 0.5857 (2) | 0.47949 (4) | 0.0183 (3) | |
C2 | 0.5853 (2) | 0.6622 (2) | 0.44055 (5) | 0.0166 (3) | |
O3 | 0.83154 (17) | 0.58840 (19) | 0.44180 (4) | 0.0255 (3) | |
C4 | 0.4404 (2) | 0.8420 (2) | 0.39624 (5) | 0.0163 (3) | |
C5 | 0.5167 (3) | 0.8362 (2) | 0.34288 (5) | 0.0193 (3) | |
H5 | 0.6561 | 0.7149 | 0.3356 | 0.023* | 0.77 (6) |
C6 | 0.3958 (3) | 1.0022 (3) | 0.30033 (5) | 0.0228 (3) | |
C7 | 0.1997 (3) | 1.1812 (2) | 0.31099 (5) | 0.0237 (3) | |
C8 | 0.1226 (3) | 1.1921 (2) | 0.36398 (6) | 0.0235 (3) | |
C9 | 0.2420 (2) | 1.0224 (2) | 0.40602 (5) | 0.0189 (3) | |
H9 | 0.1862 | 1.0290 | 0.4425 | 0.023* | 0.73 (6) |
F10 | 0.1593 (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) |
H1 | 0.258 (4) | 0.605 (3) | 0.4759 (7) | 0.037 (5)* | |
H6 | 0.456 (3) | 0.995 (3) | 0.2630 (7) | 0.030 (4)* | |
H7 | 0.114 (3) | 1.296 (3) | 0.2808 (7) | 0.034 (4)* | |
H8 | −0.007 (3) | 1.315 (3) | 0.3730 (6) | 0.030 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0108 (5) | 0.0275 (6) | 0.0168 (5) | 0.0041 (4) | 0.0032 (4) | 0.0053 (4) |
C2 | 0.0118 (6) | 0.0233 (6) | 0.0149 (5) | 0.0003 (4) | 0.0029 (4) | −0.0014 (4) |
O3 | 0.0128 (5) | 0.0416 (6) | 0.0234 (5) | 0.0072 (4) | 0.0066 (3) | 0.0104 (4) |
C4 | 0.0112 (5) | 0.0201 (6) | 0.0170 (6) | −0.0023 (4) | 0.0011 (4) | −0.0004 (4) |
C5 | 0.0167 (6) | 0.0225 (6) | 0.0185 (6) | 0.0016 (5) | 0.0030 (5) | −0.0002 (5) |
C6 | 0.0233 (7) | 0.0274 (7) | 0.0171 (6) | −0.0013 (5) | 0.0028 (5) | 0.0017 (5) |
C7 | 0.0205 (6) | 0.0231 (6) | 0.0251 (6) | −0.0002 (5) | −0.0019 (5) | 0.0073 (5) |
C8 | 0.0192 (6) | 0.0191 (6) | 0.0324 (7) | 0.0032 (5) | 0.0052 (5) | 0.0007 (5) |
C9 | 0.0171 (6) | 0.0202 (6) | 0.0200 (6) | −0.0013 (5) | 0.0050 (5) | −0.0017 (4) |
F10 | 0.0267 (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—C2 | 1.3354 (16) | C6—C7 | 1.3824 (19) |
N1—N1i | 1.384 (2) | C6—H6 | 0.989 (15) |
N1—H1 | 0.84 (2) | C7—C8 | 1.3856 (19) |
C2—O3 | 1.2315 (14) | C7—H7 | 0.971 (17) |
C2—C4 | 1.4875 (16) | C8—C9 | 1.3822 (18) |
C4—C9 | 1.3890 (17) | C8—H8 | 0.945 (17) |
C4—C5 | 1.3916 (17) | C9—F10 | 1.373 (4) |
C5—F10' | 1.299 (5) | C9—H9 | 0.9600 |
C5—C6 | 1.3797 (18) | F10—H9 | 0.4136 |
C5—H5 | 0.9600 | F10'—H5 | 0.3448 |
| | | |
C2—N1—N1i | 117.97 (12) | C5—C6—C7 | 119.69 (12) |
C2—N1—H1 | 123.5 (11) | C5—C6—H6 | 119.3 (10) |
N1i—N1—H1 | 116.7 (12) | C7—C6—H6 | 121.0 (10) |
O3—C2—N1 | 121.31 (11) | C6—C7—C8 | 120.16 (12) |
O3—C2—C4 | 121.94 (11) | C6—C7—H7 | 119.4 (10) |
N1—C2—C4 | 116.75 (10) | C8—C7—H7 | 120.4 (10) |
C9—C4—C5 | 118.28 (11) | C9—C8—C7 | 119.64 (12) |
C9—C4—C2 | 123.46 (11) | C9—C8—H8 | 118.0 (9) |
C5—C4—C2 | 118.20 (10) | C7—C8—H8 | 122.3 (9) |
F10'—C5—C6 | 117.16 (18) | F10—C9—C8 | 118.83 (14) |
F10'—C5—C4 | 121.64 (17) | F10—C9—C4 | 120.10 (14) |
C6—C5—C4 | 121.15 (11) | C8—C9—C4 | 121.07 (11) |
C6—C5—H5 | 119.4 | C8—C9—H9 | 119.4 |
C4—C5—H5 | 119.5 | C4—C9—H9 | 119.5 |
| | | |
N1i—N1—C2—O3 | −1.9 (2) | F10'—C5—C6—C7 | 178.7 (2) |
N1i—N1—C2—C4 | 178.67 (12) | C4—C5—C6—C7 | 1.29 (19) |
O3—C2—C4—C9 | −147.25 (13) | C5—C6—C7—C8 | −0.64 (19) |
N1—C2—C4—C9 | 32.16 (16) | C6—C7—C8—C9 | −0.29 (19) |
O3—C2—C4—C5 | 29.97 (17) | C7—C8—C9—F10 | −178.88 (16) |
N1—C2—C4—C5 | −150.62 (11) | C7—C8—C9—C4 | 0.61 (19) |
C9—C4—C5—F10' | −178.3 (2) | C5—C4—C9—F10 | 179.49 (16) |
C2—C4—C5—F10' | 4.3 (3) | C2—C4—C9—F10 | −3.3 (2) |
C9—C4—C5—C6 | −0.97 (18) | C5—C4—C9—C8 | 0.01 (18) |
C2—C4—C5—C6 | −178.33 (11) | C2—C4—C9—C8 | 177.23 (11) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3ii | 0.84 (2) | 2.05 (2) | 2.8549 (16) | 160.4 (16) |
N1—H1···O3i | 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+1, −z+1; (ii) x−1, y, z; (iii) x−1, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C14H11FN2O2 |
Mr | 258.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 90 |
a, b, c (Å) | 4.7698 (10), 5.2435 (10), 23.913 (5) |
β (°) | 100.89 (3) |
V (Å3) | 587.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.25 × 0.20 × 0.10 |
|
Data collection |
Diffractometer | Oxford Diffraction Xcalibur diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3819, 1205, 1060 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.628 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.094, 1.07 |
No. of reflections | 1205 |
No. of parameters | 118 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.28 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | 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. |
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.