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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 68| Part 6| June 2012| Page o1643
doi:10.1107/S1600536812019484

(E)-N′-(3-Fluoro­benzyl­­idene)-4-methyl­benzohydrazide

Hua-Nan Hua and Shi-Yong Liua*

aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China
*Correspondence e-mail: liushiyong2012@yahoo.cn

(Received 30 April 2012; accepted 1 May 2012; online 5 May 2012)

In the title compound, C15H13FN2O, the dihedral angle between the benzene rings is 16.9 (2)°. The F atom and the O atom are in a syn conformation. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds to generate C(4) chains propagating along the b-axis direction.

Related literature

For hydrazones that we have reported previously, see: Liu & You (2010[Liu, S.-Y. & You, Z. (2010). Acta Cryst. E66, o1652.]); Liu & Wang (2010[Liu, S.-Y. & Wang, X. (2010). Acta Cryst. E66, o1775.]). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009[Vijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564-1569.]); Xu et al. (2009[Xu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898.]).

[Scheme 1]

Experimental

Crystal data

  • C15H13FN2O

  • Mr = 256.27

  • Orthorhombic, P b c a

  • a = 13.2629 (5) Å

  • b = 7.9118 (3) Å

  • c = 24.9235 (8) Å

  • V = 2615.31 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.17 × 0.15 × 0.15 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.986

  • 26269 measured reflections

  • 2424 independent reflections

  • 1997 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.123

  • S = 1.04

  • 2424 reflections

  • 176 parameters

  • 1 restraint

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.90 (1) 2.04 (1) 2.9322 (17) 169 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019484/hb6775sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019484/hb6775Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019484/hb6775Isup3.cml

checkCIF report


Comment top

The crystal structures of hydrazones are of ongoing interest (Vijayakumar et al., 2009). As a continuation of our work on similar compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The two benzene ring system are inclined at a dihedral angle of 16.9 (2)°. All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N–H···O hydrogen bonds, to form one-dimensional chains running along the b axis (Fig. 2 and Table 1).

Related literature top

For hydrazones that we have reported previously, see: Liu & You (2010); Liu & Wang (2010). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 3-fluorobenzaldehyde (0.05 mol, 6.2 g) and 4-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (100 ml) at ambient temperature. Colourless blocks were obtained by slow evaporation of the solution for several days.

Refinement top

H2 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. The remaining H atoms were positioned geometrically and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C15).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.
(E)-N'-(3-Fluorobenzylidene)-4-methylbenzohydrazide top
Crystal data top
C15H13FN2ODx = 1.302 Mg m−3
Mr = 256.27Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 12661 reflections
a = 13.2629 (5) Åθ = 2.4–26.6°
b = 7.9118 (3) ŵ = 0.09 mm−1
c = 24.9235 (8) ÅT = 298 K
V = 2615.31 (16) Å3Block, colourless
Z = 80.17 × 0.15 × 0.15 mm
F(000) = 1072
Data collection top
Bruker SMART CCD
diffractometer		2424 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −15→16
Tmin = 0.984, Tmax = 0.986k = −9→9
26269 measured reflectionsl = −26→30
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0664P)2 + 0.6653P]
where P = (Fo2 + 2Fc2)/3
2424 reflections(Δ/σ)max < 0.001
176 parametersΔρmax = 0.33 e Å−3
1 restraintΔρmin = −0.21 e Å−3
Crystal data top
C15H13FN2OV = 2615.31 (16) Å3
Mr = 256.27Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.2629 (5) ŵ = 0.09 mm−1
b = 7.9118 (3) ÅT = 298 K
c = 24.9235 (8) Å0.17 × 0.15 × 0.15 mm
Data collection top
Bruker SMART CCD
diffractometer		2424 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1997 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.986Rint = 0.027
26269 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.33 e Å−3
2424 reflectionsΔρmin = −0.21 e Å−3
176 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 > 2sigma(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*/Ueq
F10.78383 (10)1.16955 (17)0.83669 (4)0.0913 (4)
N10.77048 (10)0.87893 (16)0.65528 (5)0.0465 (3)
N20.74744 (10)0.79810 (16)0.60759 (5)0.0479 (3)
O10.63068 (8)0.99556 (13)0.58731 (4)0.0490 (3)
C10.86862 (11)0.87814 (19)0.73528 (6)0.0455 (4)
C20.81042 (12)0.9977 (2)0.76159 (6)0.0511 (4)
H2A0.75161.03880.74610.061*
C30.84119 (13)1.0540 (2)0.81085 (6)0.0544 (4)
C40.92785 (14)0.9988 (2)0.83548 (6)0.0575 (4)
H40.94701.04000.86890.069*
C50.98513 (14)0.8808 (2)0.80907 (7)0.0614 (5)
H51.04440.84180.82460.074*
C60.95580 (13)0.8195 (2)0.75978 (6)0.0568 (4)
H60.99480.73790.74270.068*
C70.83918 (12)0.8096 (2)0.68307 (6)0.0486 (4)
H70.87130.71360.67000.058*
C80.67452 (11)0.86358 (18)0.57603 (5)0.0406 (3)
C90.64991 (11)0.76616 (18)0.52671 (5)0.0413 (3)
C100.55246 (12)0.7776 (2)0.50671 (6)0.0528 (4)
H100.50520.84510.52410.063*
C110.52533 (14)0.6893 (2)0.46127 (7)0.0610 (5)
H110.45940.69690.44880.073*
C120.59315 (13)0.5906 (2)0.43399 (6)0.0540 (4)
C130.69117 (13)0.5831 (2)0.45316 (6)0.0547 (4)
H130.73890.51930.43480.066*
C140.71912 (12)0.6688 (2)0.49895 (6)0.0499 (4)
H140.78510.66100.51130.060*
C150.56269 (19)0.4938 (3)0.38453 (8)0.0806 (6)
H15A0.49050.48640.38290.121*
H15B0.59080.38210.38600.121*
H15C0.58730.55120.35320.121*
H20.7769 (14)0.6969 (16)0.6020 (8)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1050 (10)0.0996 (9)0.0693 (7)0.0196 (8)−0.0026 (6)−0.0352 (7)
N10.0550 (8)0.0461 (7)0.0383 (6)−0.0006 (6)−0.0032 (5)−0.0095 (6)
N20.0587 (8)0.0447 (7)0.0404 (7)0.0068 (6)−0.0079 (6)−0.0115 (5)
O10.0539 (6)0.0436 (6)0.0495 (6)0.0052 (5)0.0031 (5)−0.0070 (5)
C10.0524 (8)0.0445 (8)0.0398 (8)−0.0040 (7)−0.0021 (6)−0.0010 (6)
C20.0546 (9)0.0536 (9)0.0452 (9)0.0010 (7)−0.0062 (7)−0.0052 (7)
C30.0666 (10)0.0526 (9)0.0439 (8)−0.0038 (8)0.0036 (7)−0.0089 (7)
C40.0739 (11)0.0597 (10)0.0390 (8)−0.0164 (9)−0.0092 (8)0.0003 (7)
C50.0638 (10)0.0673 (11)0.0532 (9)−0.0023 (9)−0.0163 (8)0.0061 (9)
C60.0613 (10)0.0582 (10)0.0509 (9)0.0069 (8)−0.0062 (8)−0.0037 (8)
C70.0562 (9)0.0468 (8)0.0427 (8)0.0036 (7)−0.0028 (7)−0.0070 (7)
C80.0447 (8)0.0385 (7)0.0385 (7)−0.0020 (6)0.0045 (6)−0.0009 (6)
C90.0489 (8)0.0374 (7)0.0378 (7)0.0004 (6)−0.0020 (6)0.0013 (6)
C100.0514 (9)0.0525 (9)0.0545 (9)0.0080 (7)−0.0060 (7)−0.0057 (7)
C110.0565 (10)0.0663 (11)0.0602 (10)0.0056 (8)−0.0186 (8)−0.0059 (9)
C120.0715 (10)0.0489 (9)0.0415 (8)0.0001 (8)−0.0133 (7)−0.0010 (7)
C130.0673 (10)0.0565 (10)0.0402 (8)0.0120 (8)−0.0040 (7)−0.0082 (7)
C140.0514 (9)0.0580 (9)0.0402 (8)0.0087 (7)−0.0062 (6)−0.0056 (7)
C150.1006 (16)0.0834 (14)0.0579 (11)−0.0013 (12)−0.0259 (11)−0.0184 (10)
Geometric parameters (Å, º) top
F1—C31.352 (2)C7—H70.9300
N1—C71.269 (2)C8—C91.487 (2)
N1—N21.3841 (16)C9—C141.384 (2)
N2—C81.3498 (19)C9—C101.388 (2)
N2—H20.902 (9)C10—C111.378 (2)
O1—C81.2278 (17)C10—H100.9300
C1—C21.386 (2)C11—C121.372 (2)
C1—C61.388 (2)C11—H110.9300
C1—C71.463 (2)C12—C131.386 (2)
C2—C31.368 (2)C12—C151.506 (2)
C2—H2A0.9300C13—C141.378 (2)
C3—C41.374 (3)C13—H130.9300
C4—C51.372 (3)C14—H140.9300
C4—H40.9300C15—H15A0.9600
C5—C61.377 (2)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—H60.9300
C7—N1—N2115.30 (13)O1—C8—C9121.74 (13)
C8—N2—N1118.77 (12)N2—C8—C9116.10 (12)
C8—N2—H2124.2 (13)C14—C9—C10118.31 (14)
N1—N2—H2116.6 (13)C14—C9—C8123.80 (13)
C2—C1—C6118.96 (14)C10—C9—C8117.87 (13)
C2—C1—C7121.69 (14)C11—C10—C9120.35 (15)
C6—C1—C7119.33 (14)C11—C10—H10119.8
C3—C2—C1118.74 (15)C9—C10—H10119.8
C3—C2—H2A120.6C12—C11—C10121.65 (16)
C1—C2—H2A120.6C12—C11—H11119.2
F1—C3—C2118.67 (16)C10—C11—H11119.2
F1—C3—C4118.20 (15)C11—C12—C13117.91 (15)
C2—C3—C4123.13 (16)C11—C12—C15121.29 (16)
C5—C4—C3117.72 (15)C13—C12—C15120.80 (17)
C5—C4—H4121.1C14—C13—C12121.13 (15)
C3—C4—H4121.1C14—C13—H13119.4
C4—C5—C6120.76 (16)C12—C13—H13119.4
C4—C5—H5119.6C13—C14—C9120.62 (14)
C6—C5—H5119.6C13—C14—H14119.7
C5—C6—C1120.67 (16)C9—C14—H14119.7
C5—C6—H6119.7C12—C15—H15A109.5
C1—C6—H6119.7C12—C15—H15B109.5
N1—C7—C1121.10 (15)H15A—C15—H15B109.5
N1—C7—H7119.4C12—C15—H15C109.5
C1—C7—H7119.4H15A—C15—H15C109.5
O1—C8—N2122.16 (13)H15B—C15—H15C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (1)2.04 (1)2.9322 (17)169 (2)
Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formulaC15H13FN2O
Mr256.27
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)13.2629 (5), 7.9118 (3), 24.9235 (8)
V (Å3)2615.31 (16)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.17 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.984, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections		26269, 2424, 1997
Rint0.027
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.123, 1.04
No. of reflections2424
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.21

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.902 (9)2.043 (10)2.9322 (17)168.5 (19)
Symmetry code: (i) −x+3/2, y−1/2, z.
 

Acknowledgements

The authors acknowledge the Zhejiang Provincial Natural Science Foundation of China (project No. Y12B020017).

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationLiu, S.-Y. & Wang, X. (2010). Acta Cryst. E66, o1775.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLiu, S.-Y. & You, Z. (2010). Acta Cryst. E66, o1652.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationShafiq, Z., Yaqub, M., Tahir, M. N., Hussain, A. & Iqbal, M. S. (2009). Acta Cryst. E65, o2898.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVijayakumar, S., Adhikari, A., Kalluraya, B. & Chandrasekharan, K. (2009). Opt. Mater. 31, 1564–1569.  Web of Science CrossRef CAS Google Scholar
 First citationXu, L., Huang, S.-S., Zhang, B.-J., Wang, S.-Y. & Zhang, H.-L. (2009). Acta Cryst. E65, o2412.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 6| June 2012| Page o1643
doi:10.1107/S1600536812019484
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