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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o233
https://doi.org/10.1107/S1600536810053043

N′-(2-Chloro­benzyl­­idene)-2-fluoro­benzohydrazide

Wei-Guang Zhanga*

aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
*Correspondence e-mail: zhangweiguang1230@163.com

(Received 1 December 2010; accepted 17 December 2010; online 24 December 2010)

The title hydrazone compound, C14H10ClFN2O, adopts an E configuration about the C=N double bond. The dihedral angle between the two substituted benzene rings is 11.6 (2)°. The F atom is disordered over two sites with occupancies of 0.488 (2) and 0.512 (2). In the crystal, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains along the a axis. C—H⋯F and C—H⋯O inter­actions also occur.

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]); Angelusiu et al. (2010[Angelusiu, M. V., Barbuceanu, S. F., Draghici, C. & Almajan, G. L. (2010). Eur. J. Med. Chem. 45, 2055-2062.]); Zhang et al. (2010[Zhang, Y. H., Zhang, L., Liu, L., Guo, J. X., Wu, D. L., Xu, G. C., Wang, X. H. & Jia, D. Z. (2010). Inorg. Chim. Acta, 363, 289-293.]); Horiuchi et al. (2009[Horiuchi, T., Nagata, M., Kitagawab, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 7850-7860.]). For the crystal structures of hydrazone compounds, see: Ban (2010[Ban, H.-Y. (2010). Acta Cryst. E66, o3240.]); Hussain et al. (2010[Hussain, A., Shafiq, Z., Tahir, M. N. & Yaqub, M. (2010). Acta Cryst. E66, o1888.]); Shalash et al. (2010[Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.]); Khaledi et al. (2009[Khaledi, H., Saharin, S. M., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2009). Acta Cryst. E65, o1920.]).

[Scheme 1]

Experimental

Crystal data

  • C14H10ClFN2O

  • Mr = 276.69

  • Monoclinic, P 21 /n

  • a = 7.1110 (14) Å

  • b = 25.291 (3) Å

  • c = 7.6560 (15) Å

  • β = 111.472 (3)°

  • V = 1281.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 298 K

  • 0.20 × 0.17 × 0.17 mm
Data collection

  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.942, Tmax = 0.950

  • 10805 measured reflections

  • 2734 independent reflections

  • 1771 reflections with I > 2σ(I)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.123

  • S = 1.03

  • 2734 reflections

  • 185 parameters

  • 3 restraints

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

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.86 (2) 2.07 (2) 2.912 (2) 167 (2)
C3—H3⋯F1Aii 0.93 2.40 3.259 (2) 154 (2)
C7—H7⋯O1i 0.93 2.50 3.270 (2) 140 (2)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810053043/om2388sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810053043/om2388Isup2.hkl

checkCIF report


Comment top

Benzoylhydrazones are a kind of special Schiff base bearing the –C(O)—NH—N=CH– groups. The hydrazone compounds have received much attention for their excellent biological properties (Ajani et al., 2010; Angelusiu et al., 2010; Zhang et al., 2010; Horiuchi et al., 2009) as well as their crystal structures (Ban, 2010; Hussain et al., 2010; Shalash et al., 2010; Khaledi et al., 2009). In the present paper, the title new hydrazone compound is reported.

The compound adopts an E configuration about the C═N double bond (Fig. 1). The dihedral angle between the two substituted benzene rings is 11.6 (2)°. The F atom is disordered over two sites with occupancies of 0.488 (2) and 0.512 (2). There is an intramolecular N—H···F hydrogen bond in the molecule. In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2). Moreover, there still presence of one non-classical C—H···F hydrogen bonding (Table 1), and one weak pi-pi interaction with centroid-centroid distance of 3.712 (2) Å.

Related literature top

For the biological properties of hydrazone compounds, see: Ajani et al. (2010); Angelusiu et al. (2010); Zhang et al. (2010); Horiuchi et al. (2009). For the crystal structures of hydrazone comounds, see: Ban (2010); Hussain et al. (2010); Shalash et al. (2010); Khaledi et al. (2009).

Experimental top

2-Chlorobenzaldehyde (0.140 g, 1 mmol) and 2-fluorobenzohydrazide (0.154 g, 1 mmol) were mixed in 50 ml me thanol. The mixture was stirred and refluxed for 30 min and cooled to room temperature to give a colorless solution. Colorless block-shaped single crystals were obtained on slow evaporation of the solution in air.

Refinement top

H2 was located in a difference Fourier map and refined with the N—H distance restrained to 0.86 (1) Å. The remaining H atoms were positioned geometrically, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C). The F atom is disordered over two sites with occupancies of 0.512 (2) and 0.488 (2). The C-F distance was restrained (DFIX) to a target value of 1.350 (5) Å.

Structure description top

Benzoylhydrazones are a kind of special Schiff base bearing the –C(O)—NH—N=CH– groups. The hydrazone compounds have received much attention for their excellent biological properties (Ajani et al., 2010; Angelusiu et al., 2010; Zhang et al., 2010; Horiuchi et al., 2009) as well as their crystal structures (Ban, 2010; Hussain et al., 2010; Shalash et al., 2010; Khaledi et al., 2009). In the present paper, the title new hydrazone compound is reported.

The compound adopts an E configuration about the C═N double bond (Fig. 1). The dihedral angle between the two substituted benzene rings is 11.6 (2)°. The F atom is disordered over two sites with occupancies of 0.488 (2) and 0.512 (2). There is an intramolecular N—H···F hydrogen bond in the molecule. In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2). Moreover, there still presence of one non-classical C—H···F hydrogen bonding (Table 1), and one weak pi-pi interaction with centroid-centroid distance of 3.712 (2) Å.

For the biological properties of hydrazone compounds, see: Ajani et al. (2010); Angelusiu et al. (2010); Zhang et al. (2010); Horiuchi et al. (2009). For the crystal structures of hydrazone comounds, see: Ban (2010); Hussain et al. (2010); Shalash et al. (2010); Khaledi et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted for clarity.
i>N'-(2-Chlorobenzylidene)-2-fluorobenzohydrazide top
Crystal data top
C14H10ClFN2OF(000) = 568
Mr = 276.69Dx = 1.434 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1387 reflections
a = 7.1110 (14) Åθ = 2.5–24.6°
b = 25.291 (3) ŵ = 0.30 mm−1
c = 7.6560 (15) ÅT = 298 K
β = 111.472 (3)°Block, colorless
V = 1281.3 (4) Å30.20 × 0.17 × 0.17 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		2734 independent reflections
Radiation source: fine-focus sealed tube1771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→9
Tmin = 0.942, Tmax = 0.950k = −32→32
10805 measured reflectionsl = −9→9
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2578P]
where P = (Fo2 + 2Fc2)/3
2734 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.20 e Å−3
3 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C14H10ClFN2OV = 1281.3 (4) Å3
Mr = 276.69Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.1110 (14) ŵ = 0.30 mm−1
b = 25.291 (3) ÅT = 298 K
c = 7.6560 (15) Å0.20 × 0.17 × 0.17 mm
β = 111.472 (3)°
Data collection top
Bruker APEXII
diffractometer		2734 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1771 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.950Rint = 0.050
10805 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0533 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å−3
2734 reflectionsΔρmin = −0.17 e Å−3
185 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Cl10.79975 (13)0.45321 (3)0.51687 (11)0.0759 (3)
F1A0.6784 (6)0.24779 (12)0.8540 (4)0.0821 (14)0.512 (4)
F1B0.7132 (5)0.09899 (12)0.5057 (4)0.0719 (13)0.488 (4)
O10.5332 (3)0.19241 (6)0.3381 (2)0.0543 (5)
N10.6941 (3)0.29004 (7)0.3616 (2)0.0414 (5)
N20.7342 (3)0.25676 (8)0.5135 (3)0.0445 (5)
H20.826 (3)0.2667 (9)0.617 (3)0.053*
C10.7557 (4)0.42979 (10)0.2922 (3)0.0478 (6)
C20.7356 (3)0.37588 (9)0.2559 (3)0.0401 (5)
C30.7001 (4)0.35952 (10)0.0726 (3)0.0489 (6)
H30.68450.32370.04350.059*
C40.6877 (4)0.39541 (13)−0.0655 (4)0.0642 (8)
H40.66630.3839−0.18660.077*
C50.7070 (5)0.44840 (13)−0.0241 (4)0.0753 (9)
H50.69710.4727−0.11830.090*
C60.7407 (4)0.46597 (11)0.1538 (4)0.0663 (8)
H60.75320.50190.18080.080*
C70.7584 (3)0.33724 (9)0.4035 (3)0.0416 (6)
H70.82000.34700.52880.050*
C80.6477 (3)0.20886 (9)0.4899 (3)0.0387 (5)
C90.6963 (3)0.17703 (9)0.6648 (3)0.0375 (5)
C100.7213 (4)0.12300 (10)0.6606 (4)0.0507 (6)
H100.71130.10710.54810.061*0.512 (4)
C110.7599 (4)0.09235 (12)0.8154 (5)0.0741 (9)
H110.77750.05610.80810.089*
C120.7729 (4)0.11456 (17)0.9811 (5)0.0805 (11)
H120.79870.09341.08670.097*
C130.7482 (4)0.16775 (16)0.9932 (4)0.0712 (9)
H130.75660.18331.10590.085*
C140.7105 (4)0.19780 (11)0.8342 (3)0.0533 (7)
H140.69380.23410.84230.064*0.488 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1118 (7)0.0547 (5)0.0717 (6)−0.0195 (4)0.0461 (5)−0.0190 (4)
F1A0.137 (3)0.059 (2)0.068 (2)−0.020 (2)0.059 (2)−0.0216 (16)
F1B0.090 (3)0.046 (2)0.082 (3)0.0040 (16)0.034 (2)−0.0095 (17)
O10.0658 (12)0.0487 (10)0.0334 (10)−0.0124 (9)0.0006 (8)−0.0030 (8)
N10.0445 (11)0.0424 (11)0.0313 (10)−0.0007 (9)0.0066 (8)0.0066 (9)
N20.0504 (13)0.0412 (11)0.0303 (11)−0.0095 (9)0.0011 (9)0.0026 (9)
C10.0509 (15)0.0456 (15)0.0503 (16)−0.0004 (12)0.0224 (12)0.0004 (12)
C20.0349 (13)0.0450 (14)0.0387 (13)0.0013 (10)0.0115 (10)0.0033 (11)
C30.0513 (15)0.0525 (15)0.0407 (15)0.0063 (12)0.0141 (12)0.0026 (12)
C40.0694 (19)0.083 (2)0.0387 (16)0.0155 (16)0.0182 (14)0.0127 (15)
C50.089 (2)0.077 (2)0.065 (2)0.0196 (18)0.0336 (18)0.0363 (18)
C60.080 (2)0.0455 (16)0.080 (2)0.0077 (14)0.0365 (18)0.0146 (15)
C70.0449 (14)0.0424 (14)0.0332 (13)−0.0030 (11)0.0093 (10)0.0003 (11)
C80.0381 (13)0.0418 (13)0.0332 (13)−0.0006 (11)0.0095 (11)−0.0022 (10)
C90.0318 (12)0.0447 (14)0.0314 (12)−0.0034 (10)0.0062 (9)0.0026 (10)
C100.0434 (15)0.0472 (15)0.0591 (17)0.0026 (12)0.0161 (13)0.0076 (14)
C110.0605 (19)0.0587 (19)0.096 (3)0.0067 (15)0.0203 (18)0.0356 (19)
C120.057 (2)0.106 (3)0.066 (2)−0.0101 (18)0.0085 (16)0.044 (2)
C130.0576 (18)0.117 (3)0.0361 (16)−0.0247 (18)0.0141 (13)0.0039 (17)
C140.0479 (15)0.0685 (19)0.0409 (16)−0.0120 (13)0.0131 (12)−0.0060 (14)
Geometric parameters (Å, º) top
Cl1—C11.736 (3)C5—C61.368 (4)
F1A—C141.303 (3)C5—H50.9300
F1B—C101.315 (3)C6—H60.9300
O1—C81.222 (2)C7—H70.9300
N1—C71.276 (3)C8—C91.491 (3)
N1—N21.379 (2)C9—C141.368 (3)
N2—C81.340 (3)C9—C101.380 (3)
N2—H20.861 (16)C10—C111.357 (4)
C1—C61.374 (3)C10—H100.9300
C1—C21.388 (3)C11—C121.360 (4)
C2—C31.395 (3)C11—H110.9300
C2—C71.457 (3)C12—C131.364 (5)
C3—C41.372 (3)C12—H120.9300
C3—H30.9300C13—C141.376 (4)
C4—C51.372 (4)C13—H130.9300
C4—H40.9300C14—H140.9300
C7—N1—N2114.48 (18)O1—C8—N2123.3 (2)
C8—N2—N1119.66 (18)O1—C8—C9121.7 (2)
C8—N2—H2123.0 (16)N2—C8—C9114.99 (19)
N1—N2—H2116.9 (16)C14—C9—C10115.9 (2)
C6—C1—C2121.7 (2)C14—C9—C8123.8 (2)
C6—C1—Cl1118.2 (2)C10—C9—C8120.2 (2)
C2—C1—Cl1120.10 (19)F1B—C10—C11116.9 (3)
C1—C2—C3117.4 (2)F1B—C10—C9121.0 (3)
C1—C2—C7122.0 (2)C11—C10—C9122.1 (3)
C3—C2—C7120.6 (2)C11—C10—H10118.9
C4—C3—C2121.1 (2)C9—C10—H10118.9
C4—C3—H3119.5C10—C11—C12120.1 (3)
C2—C3—H3119.5C10—C11—H11119.9
C3—C4—C5119.7 (3)C12—C11—H11119.9
C3—C4—H4120.1C11—C12—C13120.3 (3)
C5—C4—H4120.1C11—C12—H12119.9
C6—C5—C4120.9 (3)C13—C12—H12119.9
C6—C5—H5119.6C12—C13—C14118.2 (3)
C4—C5—H5119.6C12—C13—H13120.9
C5—C6—C1119.2 (3)C14—C13—H13120.9
C5—C6—H6120.4F1A—C14—C9121.8 (3)
C1—C6—H6120.4F1A—C14—C13114.8 (3)
N1—C7—C2120.3 (2)C9—C14—C13123.3 (3)
N1—C7—H7119.9C9—C14—H14118.3
C2—C7—H7119.9C13—C14—H14118.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.86 (2)2.07 (2)2.912 (2)167 (2)
N2—H2···F1A0.86 (2)2.45 (2)2.785 (2)104 (2)
C3—H3···F1Aii0.932.403.259 (2)154 (2)
C7—H7···O1i0.932.503.270 (2)140 (2)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formulaC14H10ClFN2O
Mr276.69
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.1110 (14), 25.291 (3), 7.6560 (15)
β (°) 111.472 (3)
V (Å3)1281.3 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.20 × 0.17 × 0.17
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.942, 0.950
No. of measured, independent and
observed [I > 2σ(I)] reflections		10805, 2734, 1771
Rint0.050
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.123, 1.03
No. of reflections2734
No. of parameters185
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.17

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.861 (16)2.067 (17)2.912 (2)167 (2)
N2—H2···F1A0.86 (2)2.45 (2)2.785 (2)104 (2)
C3—H3···F1Aii0.932.403.259 (2)154 (2)
C7—H7···O1i0.932.503.270 (2)140 (2)
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, y, z−1.
 

Acknowledgements

Financial support fromd Qiqihar University is acknowledged.

References

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o233
https://doi.org/10.1107/S1600536810053043
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