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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160304
doi:10.1107/S2414314616003047

(E)-4-Chloro-N′-(2,4,5-tri­fluoro­benzyl­­idene)benzohydrazide

R. Maheswari,a J. Manjulab* and B. Gunasekaranc

aDepartment of Chemistry, Saranathan College of Engineering, Tiruchirappalli, Tamilnadu, India, bPG and Research Department of Chemistry, Periyar EVR College, Tiruchirappalli, Tamilnadu, India, and cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
*Correspondence e-mail: swaroopapranav@gmail.com, phdguna@gmail.com

Edited by H. Ishida, Okayama University, Japan (Received 14 February 2016; accepted 20 February 2016; online 2 March 2016)

The title compound, C14H8ClF3N2O, is approximately planar, with a dihedral angle of 4.73 (6)° between the planes of the chloro­phenyl and tri­fluoro­benzyl­idene rings. In the crystal, mol­ecules are stacked in a column along the b axis through π–π inter­actions [centroid–centroid distances = 3.7097 (12) and 3.7191 (12) Å].

CCDC reference: 1454889

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Hydrazones have continued to attract interest from researchers due to their medicinal applications. These derivatives exhibit anti­microbial (Pieczonka et al., 2013[Pieczonka, A. M., Strzelczyk, A., Sadowska, B., Mlostoń, G. & Stączek, P. (2013). Eur. J. Med. Chem. 64, 389-395.]), anti-proliferative (Yadagiri et al., 2014[Yadagiri, B., Holagunda, U. D., Bantu, R., Nagarapu, L., Guguloth, V., Polepally, S. & Jain, N. (2014). Bioorg. Med. Chem. Lett. 24, 5041-5044.]), anti­platelet (Mashayekhi et al., 2013[Mashayekhi, V., Haj Mohammad Ebrahim Tehrani, K., Amidi, S. & Kobarfard, F. (2013). Chem. Pharm. Bull. 61, 144-150.]), anti-hepatitis (Şenkardeş et al., 2016[Şenkardeş, S., Kaushik-Basu, N., Durmaz, İ., Manvar, D., Basu, A., Atalay, R. & Küçükgüzel, Ş. G. (2016). Eur. J. Med. Chem. 108, 301-308.]) and anti-amoebic (Siddiqui et al., 2012[Siddiqui, S. M., Salahuddin, A. & Azam, A. (2012). Eur. J. Med. Chem. 49, 411-416.]) activities.

The geometric parameters of the title mol­ecule (Fig. 1[link]) agree well with those reported for similar structures (Sreeja et al., 2013[Sreeja, P. B., Sithambaresan, M., Aiswarya, N. & Kurup, M. R. P. (2013). Acta Cryst. E69, o1828.]; Nair et al., 2012[Nair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.]). The chloro­phenyl ring makes a dihedral angle of 4.73 (6)° with the tri­fluoro­benzyl­idene ring. In the crystal, the mol­ecules are linked by π–π inter­actions [Cg1⋯Cg2i = 3. 7191 (12) Å and Cg1⋯Cg2ii = 3. 7096 (12) Å; symmetry codes: (i) 1 − x, −y, 2 − z; (ii) 1 − x, 1 − y, 2 − z]; Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively;

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Synthesis and crystallization

To an ethano­lic solution of 4-chloro­benzohydrazide (0.17 g, 0.001 mol), 2,4,5-tri­fluoro benzaldehyde (0.1 mL, 0.001 mol) and a few drops of conc. HCl were added. The reaction mixture was stirred well at room temperature for 30 min. The insoluble solid gradually generated was filtered and washed with petroleum benzine (60–80°C) and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO solution (yield 98%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C14H8ClF3N2O
Mr 312.67
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 295
a, b, c (Å) 6.4998 (2), 7.4286 (2), 14.8289 (4)
α, β, γ (°) 84.859 (2), 86.707 (2), 83.313 (2)
V (Å3) 707.47 (3)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.30
Crystal size (mm) 0.18 × 0.16 × 0.11
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.948, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections 10440, 2925, 2162
Rint 0.025
(sin θ/λ)max (Å−1) 0.628
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.120, 0.99
No. of reflections 2925
No. of parameters 191
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.21, −0.18
Computer programs: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data

CCDC reference: 1454889

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616003047/is4002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003047/is4002Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003047/is4002Isup3.cml

checkCIF report


Comment top

Hydrazones have continued to attract researchers due to their medicinal applications. These derivatives exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferative (Yadagiri et al., 2014), antiplatelet (Mashayekhi et al., 2013), anti-hepatitis (Şenkardeş et al., 2016) and antiamoebic (Siddiqui et al., 2012) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Sreeja et al., 2013; Nair et al., 2012). The chlorophenyl ring makes a dihedral angles of 4.73 (6)° with the trifluorobenzylidene ring. The molecules are linked by π–π interactions [Cg1···Cg2i = 3. 7191 (12) Å and Cg1···Cg2ii = 3. 7096 (12) Å; symmetry codes: (i) 1 − x, −y, 2 − z; (ii) 1 − x, 1 − y, 2 − z]; Cg1 and Cg2 are the centroids of C1–C6 and C9–C14 rings, respectively

Experimental top

To an ethanolic solution of 4-chlorobenzohydrazide (0.17 g, 0.001 mol), 2,4,5-trifluoro benzaldehyde (0.1 ml, 0.001 mol) and a few drops of conc. HCl were added. The reaction mixture was stirred well at room temperature for 30 min. The insoluble solid gradually generated was filtered and washed with petroleum benzine (60–80°C) and dried in a vacuum desiccator. The crude solid was recrystallized from DMSO (yield 98%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Structure description top

Hydrazones have continued to attract researchers due to their medicinal applications. These derivatives exhibit antimicrobial (Pieczonka et al., 2013), anti-proliferative (Yadagiri et al., 2014), antiplatelet (Mashayekhi et al., 2013), anti-hepatitis (Şenkardeş et al., 2016) and anti-amoebic (Siddiqui et al., 2012) activities.

The geometric parameters of the title molecule (Fig. 1) agree well with those reported for similar structures (Sreeja et al., 2013; Nair et al., 2012). The chlorophenyl ring makes a dihedral angle of 4.73 (6)° with the trifluorobenzylidene ring. The molecules are linked by π–π interactions [Cg1···Cg2i = 3. 7191 (12) Å and Cg1···Cg2ii = 3. 7096 (12) Å; symmetry codes: (i) 1 − x, −y, 2 − z; (ii) 1 − x, 1 − y, 2 − z]; Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
(E)-4-Chloro-N'-(2,4,5-trifluorobenzylidene)benzohydrazide top
Crystal data top
C14H8ClF3N2OZ = 2
Mr = 312.67F(000) = 316
Triclinic, P1Dx = 1.468 Mg m−3
a = 6.4998 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4286 (2) ÅCell parameters from 2925 reflections
c = 14.8289 (4) Åθ = 1.4–26.5°
α = 84.859 (2)°µ = 0.30 mm−1
β = 86.707 (2)°T = 295 K
γ = 83.313 (2)°Block, colourless
V = 707.47 (3) Å30.18 × 0.16 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer		2925 independent reflections
Radiation source: fine-focus sealed tube2162 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 0 pixels mm-1θmax = 26.5°, θmin = 1.4°
ω and φ scansh = −8→8
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −9→9
Tmin = 0.948, Tmax = 0.968l = −18→18
10440 measured 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2152P]
where P = (Fo2 + 2Fc2)/3
2925 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C14H8ClF3N2Oγ = 83.313 (2)°
Mr = 312.67V = 707.47 (3) Å3
Triclinic, P1Z = 2
a = 6.4998 (2) ÅMo Kα radiation
b = 7.4286 (2) ŵ = 0.30 mm−1
c = 14.8289 (4) ÅT = 295 K
α = 84.859 (2)°0.18 × 0.16 × 0.11 mm
β = 86.707 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2925 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2162 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.968Rint = 0.025
10440 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 0.99Δρmax = 0.21 e Å−3
2925 reflectionsΔρmin = −0.18 e Å−3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.18109 (10)0.17309 (9)0.53712 (4)0.0773 (2)
F10.21764 (19)0.46649 (19)1.23486 (9)0.0731 (4)
F20.7236 (3)0.3478 (2)1.45102 (8)0.0871 (5)
N20.5848 (2)0.2425 (2)1.03868 (10)0.0488 (4)
N10.4890 (2)0.2335 (2)0.95876 (10)0.0489 (4)
H10.35800.26560.95550.059*
F30.9897 (2)0.19270 (19)1.32932 (8)0.0738 (4)
C40.4866 (3)0.1731 (2)0.80147 (11)0.0429 (4)
C50.2782 (3)0.2351 (3)0.79365 (12)0.0479 (4)
H50.20050.27720.84370.058*
C80.4666 (3)0.3037 (3)1.10238 (13)0.0497 (4)
H80.32780.34101.09180.060*
C20.5077 (3)0.1097 (3)0.64454 (13)0.0542 (5)
H20.58420.06760.59420.065*
C70.6013 (3)0.1743 (3)0.88617 (13)0.0494 (4)
C130.4658 (4)0.4083 (3)1.34516 (13)0.0578 (5)
H130.37280.46191.38760.069*
C60.1850 (3)0.2352 (3)0.71227 (12)0.0500 (5)
H60.04530.27710.70730.060*
O10.7870 (2)0.1260 (3)0.88799 (10)0.0826 (5)
C10.3014 (3)0.1725 (3)0.63871 (12)0.0499 (5)
C90.5423 (3)0.3175 (2)1.19213 (12)0.0455 (4)
C140.4111 (3)0.3957 (3)1.25786 (13)0.0511 (5)
C100.7425 (3)0.2490 (3)1.21677 (12)0.0483 (4)
H100.83680.19591.17470.058*
C30.5999 (3)0.1097 (3)0.72598 (13)0.0492 (4)
H30.73960.06700.73050.059*
C110.7985 (3)0.2609 (3)1.30357 (13)0.0519 (5)
C120.6613 (4)0.3393 (3)1.36670 (13)0.0574 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0880 (5)0.1003 (5)0.0470 (3)−0.0101 (3)−0.0175 (3)−0.0158 (3)
F10.0537 (7)0.0842 (9)0.0778 (8)0.0098 (6)0.0005 (6)−0.0118 (7)
F20.1174 (12)0.1016 (11)0.0447 (6)−0.0074 (9)−0.0183 (7)−0.0162 (7)
N20.0461 (9)0.0574 (10)0.0442 (8)−0.0059 (7)−0.0099 (7)−0.0063 (7)
N10.0406 (8)0.0628 (10)0.0442 (8)−0.0019 (7)−0.0091 (6)−0.0106 (7)
F30.0619 (8)0.0937 (10)0.0658 (7)−0.0006 (7)−0.0223 (6)−0.0040 (7)
C40.0417 (10)0.0439 (10)0.0433 (9)−0.0049 (7)−0.0022 (7)−0.0047 (7)
C50.0405 (10)0.0593 (11)0.0436 (9)0.0005 (8)0.0005 (7)−0.0117 (8)
C80.0459 (10)0.0553 (11)0.0490 (10)−0.0060 (8)−0.0069 (8)−0.0070 (8)
C20.0591 (12)0.0582 (12)0.0456 (10)−0.0056 (9)0.0084 (9)−0.0140 (9)
C70.0414 (10)0.0577 (11)0.0488 (10)−0.0044 (8)−0.0040 (8)−0.0041 (8)
C130.0728 (14)0.0519 (12)0.0480 (10)−0.0064 (10)0.0095 (10)−0.0092 (9)
C60.0412 (10)0.0596 (12)0.0494 (10)0.0000 (8)−0.0062 (8)−0.0098 (8)
O10.0419 (8)0.1419 (16)0.0626 (9)0.0102 (9)−0.0110 (7)−0.0215 (9)
C10.0579 (12)0.0519 (11)0.0417 (9)−0.0089 (9)−0.0056 (8)−0.0082 (8)
C90.0501 (10)0.0434 (10)0.0444 (9)−0.0106 (8)−0.0039 (8)−0.0039 (8)
C140.0507 (11)0.0472 (10)0.0549 (11)−0.0041 (8)0.0001 (9)−0.0045 (8)
C100.0502 (11)0.0502 (11)0.0455 (9)−0.0073 (8)−0.0032 (8)−0.0065 (8)
C30.0414 (10)0.0524 (11)0.0533 (10)−0.0012 (8)0.0014 (8)−0.0092 (8)
C110.0562 (12)0.0507 (11)0.0497 (10)−0.0081 (9)−0.0106 (9)−0.0007 (8)
C120.0786 (15)0.0541 (12)0.0417 (10)−0.0123 (10)−0.0078 (9)−0.0064 (8)
Geometric parameters (Å, º) top
Cl1—C11.7363 (18)C2—C11.372 (3)
F1—C141.356 (2)C2—C31.379 (3)
F2—C121.345 (2)C2—H20.9300
N2—C81.266 (2)C7—O11.220 (2)
N2—N11.380 (2)C13—C121.358 (3)
N1—C71.343 (2)C13—C141.376 (3)
N1—H10.8600C13—H130.9300
F3—C111.349 (2)C6—C11.376 (3)
C4—C51.387 (3)C6—H60.9300
C4—C31.391 (2)C9—C141.380 (3)
C4—C71.498 (2)C9—C101.397 (3)
C5—C61.381 (2)C10—C111.371 (2)
C5—H50.9300C10—H100.9300
C8—C91.461 (2)C3—H30.9300
C8—H80.9300C11—C121.375 (3)
C8—N2—N1114.85 (15)C1—C6—H6120.4
C7—N1—N2119.69 (15)C5—C6—H6120.4
C7—N1—H1120.2C2—C1—C6121.46 (17)
N2—N1—H1120.2C2—C1—Cl1120.08 (15)
C5—C4—C3118.83 (16)C6—C1—Cl1118.46 (15)
C5—C4—C7124.05 (16)C14—C9—C10117.17 (17)
C3—C4—C7117.10 (16)C14—C9—C8119.73 (17)
C6—C5—C4120.65 (16)C10—C9—C8123.07 (17)
C6—C5—H5119.7F1—C14—C13117.91 (17)
C4—C5—H5119.7F1—C14—C9118.15 (17)
N2—C8—C9121.75 (17)C13—C14—C9123.93 (18)
N2—C8—H8119.1C11—C10—C9119.38 (18)
C9—C8—H8119.1C11—C10—H10120.3
C1—C2—C3119.12 (17)C9—C10—H10120.3
C1—C2—H2120.4C2—C3—C4120.77 (17)
C3—C2—H2120.4C2—C3—H3119.6
O1—C7—N1122.38 (17)C4—C3—H3119.6
O1—C7—C4121.28 (17)F3—C11—C10120.38 (18)
N1—C7—C4116.33 (16)F3—C11—C12118.47 (17)
C12—C13—C14117.17 (18)C10—C11—C12121.14 (19)
C12—C13—H13121.4F2—C12—C13119.85 (19)
C14—C13—H13121.4F2—C12—C11118.9 (2)
C1—C6—C5119.17 (17)C13—C12—C11121.21 (18)
C8—N2—N1—C7178.48 (18)C12—C13—C14—C90.1 (3)
C3—C4—C5—C6−0.4 (3)C10—C9—C14—F1178.60 (17)
C7—C4—C5—C6177.82 (18)C8—C9—C14—F1−3.5 (3)
N1—N2—C8—C9178.32 (16)C10—C9—C14—C13−0.5 (3)
N2—N1—C7—O10.6 (3)C8—C9—C14—C13177.41 (19)
N2—N1—C7—C4−178.52 (15)C14—C9—C10—C110.5 (3)
C5—C4—C7—O1−176.5 (2)C8—C9—C10—C11−177.34 (17)
C3—C4—C7—O11.8 (3)C1—C2—C3—C4−0.2 (3)
C5—C4—C7—N12.7 (3)C5—C4—C3—C20.5 (3)
C3—C4—C7—N1−179.10 (17)C7—C4—C3—C2−177.88 (18)
C4—C5—C6—C10.1 (3)C9—C10—C11—F3178.76 (17)
C3—C2—C1—C6−0.1 (3)C9—C10—C11—C12−0.1 (3)
C3—C2—C1—Cl1−179.75 (15)C14—C13—C12—F2180.00 (18)
C5—C6—C1—C20.2 (3)C14—C13—C12—C110.3 (3)
C5—C6—C1—Cl1179.82 (15)F3—C11—C12—F21.1 (3)
N2—C8—C9—C14175.94 (18)C10—C11—C12—F2180.00 (18)
N2—C8—C9—C10−6.3 (3)F3—C11—C12—C13−179.17 (19)
C12—C13—C14—F1−178.97 (18)C10—C11—C12—C13−0.3 (3)

Experimental details

Crystal data
Chemical formulaC14H8ClF3N2O
Mr312.67
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)6.4998 (2), 7.4286 (2), 14.8289 (4)
α, β, γ (°)84.859 (2), 86.707 (2), 83.313 (2)
V (Å3)707.47 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.18 × 0.16 × 0.11
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.948, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections		10440, 2925, 2162
Rint0.025
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.120, 0.99
No. of reflections2925
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

Acknowledgements

The authors express their thanks to the authorities of Saranathan College of Engineering, Tiruchirappalli, for providing laboratory facilities and the CAS in Crystallography and Biophysics, University of Madras, Chennai, for the data collection.

References

First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationMashayekhi, V., Haj Mohammad Ebrahim Tehrani, K., Amidi, S. & Kobarfard, F. (2013). Chem. Pharm. Bull. 61, 144–150.  CrossRef CAS PubMed Google Scholar
 First citationNair, Y., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2709.  CSD CrossRef IUCr Journals Google Scholar
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Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160304
doi:10.1107/S2414314616003047
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