N′-(4-Fluoro­benzyl­idene)-2-(4-fluoro­phen­yl)acetohydrazide

Fun, H.-K.; Hemamalini, M.; Sumangala, V.; Nagaraja, G.K.; Poojary, B.

doi:10.1107/S1600536811039845

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2835

doi:10.1107/S1600536811039845

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N′-(4-Fluorobenzylidene)-2-(4-fluorophenyl)acetohydrazide

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a V. Sumangala,^b G. K. Nagaraja ^b and Boja Poojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Mangalagangothri 574 199, Mangalore, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 22 September 2011; accepted 28 September 2011; online 5 October 2011)

In the title compound, C₁₅H₁₂F₂N₂O, the dihedral angle between the two benzene rings is 48.73 (8)°. The hydrazine group is twisted slightly, with a C—N—N—C torsion angle of 172.48 (12)°. In the crystal, molecules are connected by strong N—H⋯O and weak C—H⋯O hydrogen bonds, forming supramolecular chains along the c axis. The structure is consolidated by π–π [centroid–centroid separation = 3.6579 (10) Å] and C—H⋯π interactions.

Related literature

For further details of aroylhydrozones, see: Li & Qu (2011 ); Zhang (2011 ); Fan et al. (2008 ). Ajani et al. (2010 ); Avaji et al. (2009 ); Rasras et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₂F₂N₂O
M_r = 274.27
Monoclinic, P 2₁ /c
a = 13.8754 (15) Å
b = 12.5349 (13) Å
c = 7.7093 (8) Å
β = 93.566 (2)°
V = 1338.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.85 × 0.26 × 0.12 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.915, T_max = 0.988
17153 measured reflections
4415 independent reflections
2586 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.153
S = 1.02
4415 reflections
229 parameters
All H-atom parameters refined
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯O1ⁱ	0.892 (15)	2.013 (15)	2.8841 (14)	165.2 (14)
C4—H4⋯O1ⁱⁱ	0.92 (2)	2.47 (2)	3.370 (2)	168 (2)
C1—H1⋯Cg1ⁱⁱⁱ	0.98 (2)	2.92 (2)	3.7025 (18)	138.0 (15)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039845/hb6416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039845/hb6416Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039845/hb6416Isup3.cml

checkCIF report

Comment top

Large number of aroylhydrozones have been synthesized in the recent years (Li & Qu, 2011; Zhang, 2011; Fan et al., 2008) which can serve as intermediates in synthesizing biologically active compounds (Ajani et al., 2010; Avaji et al., 2009; Rasras et al., 2010).

The asymmetric unit of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings (C1–C6/C10–C15) is 48.73 (8)°. The hydrazine group is twisted slightly with C9-N1-N2-C8, N1-N2-C8-C7 and N2-N1-C9-C10 torsion angles of 172.48 (12)°, 169.41 (12)° and 174.13 (11)°, respectively.

In the crystal structure, (Fig. 2), the molecules are connected via intermolecular strong N—H···O and weak C—H···.O (Table 1) hydrogen bonds forming one-dimensional supramolecular chains along the c-axis. The crystal structure is further stabilized by π–π interactions between the benzene (Cg2; C10–C15) rings [Cg2···Cg2 = 3.6579 (10) Å; -x, 2-y, 1-z] and C—H···π interaction involving the centroid of the C1–C6 (Cg1) ring.

Related literature top

For further details of aroylhydrozones, see: Li & Qu (2011); Zhang (2011); Fan et al. (2008). Ajani et al. (2010); Avaji et al. (2009); Rasras et al. (2010).

Experimental top

An equimolar mixture of 2-(4-fluorophenyl)acetohydrazide and 4-fluorobenzaldehyde was refluxed for four hours in the presence of few drops of acid catalyst and ethanol as solvent. The compound obtained was filtered, washed, dried and recrystalised from ethanol to yield colourless needles.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound (I). H atoms not involved in hydrogen bonding are omitted.

N'-(4-Fluorobenzylidene)-2-(4-fluorophenyl)acetohydrazide top

Crystal data top

C₁₅H₁₂F₂N₂O	F(000) = 568
M_r = 274.27	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3867 reflections
a = 13.8754 (15) Å	θ = 3.1–28.1°
b = 12.5349 (13) Å	µ = 0.11 mm⁻¹
c = 7.7093 (8) Å	T = 296 K
β = 93.566 (2)°	Needle, colourless
V = 1338.3 (2) Å³	0.85 × 0.26 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	4415 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 31.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→18
T_min = 0.915, T_max = 0.988	k = −18→17
17153 measured reflections	l = −11→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0752P)² + 0.0834P] where P = (F_o² + 2F_c²)/3
4415 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₁₂F₂N₂O	V = 1338.3 (2) Å³
M_r = 274.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.8754 (15) Å	µ = 0.11 mm⁻¹
b = 12.5349 (13) Å	T = 296 K
c = 7.7093 (8) Å	0.85 × 0.26 × 0.12 mm
β = 93.566 (2)°

Data collection top

Bruker APEXII DUO CCD diffractometer	4415 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2586 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.988	R_int = 0.026
17153 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.153	All H-atom parameters refined
S = 1.02	Δρ_max = 0.21 e Å⁻³
4415 reflections	Δρ_min = −0.23 e Å⁻³
229 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	U_iso*/U_eq
F1	0.76995 (8)	0.61553 (12)	0.39014 (18)	0.1100 (4)
F2	−0.21176 (8)	0.96296 (11)	0.46342 (17)	0.1026 (4)
O1	0.31477 (7)	0.63023 (8)	0.33790 (11)	0.0593 (3)
N1	0.18163 (7)	0.77410 (8)	0.22901 (12)	0.0457 (2)
N2	0.26129 (8)	0.75056 (9)	0.13713 (13)	0.0486 (3)
C1	0.56239 (12)	0.71146 (14)	0.1320 (2)	0.0681 (4)
C2	0.65526 (13)	0.70642 (17)	0.2100 (3)	0.0799 (5)
C3	0.67904 (11)	0.62143 (15)	0.3128 (2)	0.0695 (4)
C4	0.61612 (13)	0.54169 (15)	0.3421 (2)	0.0693 (4)
C5	0.52362 (12)	0.54705 (12)	0.2623 (2)	0.0598 (4)
C6	0.49585 (9)	0.63228 (11)	0.15654 (15)	0.0501 (3)
C7	0.39518 (11)	0.63844 (15)	0.07075 (17)	0.0603 (4)
C8	0.32068 (9)	0.67230 (11)	0.19528 (14)	0.0478 (3)
C9	0.13383 (10)	0.85672 (11)	0.17896 (16)	0.0482 (3)
C10	0.04314 (9)	0.88361 (10)	0.25544 (15)	0.0469 (3)
C11	0.00248 (11)	0.98366 (12)	0.22675 (18)	0.0572 (3)
C12	−0.08399 (11)	1.01067 (14)	0.2957 (2)	0.0647 (4)
C13	−0.12794 (11)	0.93654 (14)	0.3933 (2)	0.0655 (4)
C14	−0.09066 (12)	0.83664 (14)	0.4254 (2)	0.0663 (4)
C15	−0.00469 (11)	0.81012 (12)	0.35531 (19)	0.0571 (3)
H1	0.5397 (14)	0.7715 (16)	0.059 (3)	0.094 (6)*
H2	0.7039 (17)	0.7598 (17)	0.196 (3)	0.101 (7)*
H4	0.6331 (15)	0.4869 (19)	0.417 (3)	0.104 (7)*
H5	0.4770 (13)	0.4897 (15)	0.275 (2)	0.079 (5)*
H7A	0.3934 (12)	0.6871 (14)	−0.029 (2)	0.074 (5)*
H7B	0.3739 (14)	0.5682 (15)	0.026 (2)	0.080 (5)*
H9	0.1566 (11)	0.9042 (12)	0.0904 (19)	0.058 (4)*
H11	0.0356 (12)	1.0384 (14)	0.157 (2)	0.071 (5)*
H12	−0.1126 (15)	1.0787 (17)	0.276 (2)	0.088 (6)*
H14	−0.1233 (15)	0.7855 (16)	0.491 (3)	0.090 (6)*
H15	0.0238 (13)	0.7400 (14)	0.374 (2)	0.073 (5)*
H1N1	0.2685 (11)	0.7821 (12)	0.035 (2)	0.061 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0595 (6)	0.1415 (12)	0.1263 (9)	0.0162 (6)	−0.0142 (6)	−0.0132 (8)
F2	0.0706 (7)	0.1242 (10)	0.1173 (9)	0.0344 (6)	0.0415 (6)	0.0197 (7)
O1	0.0625 (6)	0.0731 (7)	0.0435 (5)	0.0189 (5)	0.0134 (4)	0.0069 (4)
N1	0.0455 (5)	0.0527 (6)	0.0396 (5)	0.0043 (4)	0.0094 (4)	−0.0022 (4)
N2	0.0490 (6)	0.0616 (7)	0.0362 (5)	0.0069 (5)	0.0119 (4)	0.0018 (4)
C1	0.0654 (9)	0.0731 (10)	0.0675 (9)	0.0061 (8)	0.0180 (7)	0.0172 (8)
C2	0.0626 (10)	0.0866 (13)	0.0921 (13)	−0.0099 (9)	0.0175 (9)	0.0057 (10)
C3	0.0493 (8)	0.0895 (12)	0.0701 (9)	0.0114 (8)	0.0064 (6)	−0.0068 (8)
C4	0.0693 (10)	0.0696 (10)	0.0695 (9)	0.0247 (8)	0.0079 (7)	0.0071 (8)
C5	0.0606 (8)	0.0538 (8)	0.0664 (8)	0.0082 (7)	0.0148 (7)	0.0035 (6)
C6	0.0502 (7)	0.0589 (8)	0.0427 (6)	0.0099 (6)	0.0155 (5)	−0.0009 (5)
C7	0.0545 (8)	0.0864 (11)	0.0409 (6)	0.0146 (7)	0.0107 (5)	−0.0074 (7)
C8	0.0462 (6)	0.0611 (8)	0.0367 (5)	0.0050 (6)	0.0059 (4)	−0.0054 (5)
C9	0.0515 (7)	0.0508 (7)	0.0429 (6)	0.0015 (6)	0.0071 (5)	0.0005 (5)
C10	0.0490 (6)	0.0489 (7)	0.0429 (6)	0.0039 (5)	0.0035 (5)	−0.0028 (5)
C11	0.0612 (8)	0.0547 (8)	0.0563 (7)	0.0090 (6)	0.0092 (6)	0.0071 (6)
C12	0.0660 (9)	0.0607 (9)	0.0682 (9)	0.0205 (8)	0.0103 (7)	0.0060 (7)
C13	0.0510 (8)	0.0800 (11)	0.0669 (8)	0.0149 (7)	0.0136 (6)	0.0006 (7)
C14	0.0589 (9)	0.0680 (10)	0.0736 (9)	−0.0006 (7)	0.0185 (7)	0.0084 (8)
C15	0.0564 (8)	0.0511 (8)	0.0647 (8)	0.0042 (6)	0.0115 (6)	0.0022 (6)

Geometric parameters (Å, º) top

F1—C3	1.3633 (18)	C6—C7	1.510 (2)
F2—C13	1.3538 (17)	C7—C8	1.5146 (17)
O1—C8	1.2268 (15)	C7—H7A	0.982 (18)
N1—C9	1.2765 (16)	C7—H7B	0.984 (19)
N1—N2	1.3812 (14)	C9—C10	1.4619 (18)
N2—C8	1.3402 (17)	C9—H9	0.973 (16)
N2—H1N1	0.890 (17)	C10—C11	1.3873 (19)
C1—C6	1.377 (2)	C10—C15	1.3947 (19)
C1—C2	1.389 (3)	C11—C12	1.384 (2)
C1—H1	0.98 (2)	C11—H11	1.001 (18)
C2—C3	1.356 (3)	C12—C13	1.363 (2)
C2—H2	0.96 (2)	C12—H12	0.95 (2)
C3—C4	1.355 (3)	C13—C14	1.372 (2)
C4—C5	1.390 (2)	C14—C15	1.380 (2)
C4—H4	0.92 (2)	C14—H14	0.95 (2)
C5—C6	1.3840 (19)	C15—H15	0.971 (18)
C5—H5	0.976 (19)

C9—N1—N2	115.83 (10)	C8—C7—H7B	105.7 (11)
C8—N2—N1	118.67 (10)	H7A—C7—H7B	106.8 (15)
C8—N2—H1N1	121.3 (10)	O1—C8—N2	122.72 (11)
N1—N2—H1N1	119.7 (10)	O1—C8—C7	122.27 (12)
C6—C1—C2	121.31 (16)	N2—C8—C7	115.01 (11)
C6—C1—H1	116.0 (12)	N1—C9—C10	120.62 (12)
C2—C1—H1	122.6 (12)	N1—C9—H9	121.5 (9)
C3—C2—C1	118.30 (17)	C10—C9—H9	117.8 (9)
C3—C2—H2	117.8 (13)	C11—C10—C15	118.84 (12)
C1—C2—H2	123.9 (13)	C11—C10—C9	119.73 (12)
C4—C3—C2	122.74 (16)	C15—C10—C9	121.43 (12)
C4—C3—F1	118.37 (16)	C12—C11—C10	120.90 (14)
C2—C3—F1	118.89 (17)	C12—C11—H11	118.5 (10)
C3—C4—C5	118.51 (16)	C10—C11—H11	120.6 (10)
C3—C4—H4	120.9 (14)	C13—C12—C11	118.25 (14)
C5—C4—H4	120.5 (14)	C13—C12—H12	120.2 (12)
C6—C5—C4	120.90 (16)	C11—C12—H12	121.5 (12)
C6—C5—H5	117.8 (11)	F2—C13—C12	118.59 (15)
C4—C5—H5	121.2 (11)	F2—C13—C14	118.36 (15)
C1—C6—C5	118.24 (14)	C12—C13—C14	123.05 (14)
C1—C6—C7	120.86 (14)	C13—C14—C15	118.33 (15)
C5—C6—C7	120.90 (14)	C13—C14—H14	121.7 (12)
C6—C7—C8	112.71 (10)	C15—C14—H14	119.9 (12)
C6—C7—H7A	110.7 (10)	C14—C15—C10	120.63 (14)
C8—C7—H7A	109.8 (10)	C14—C15—H15	120.8 (10)
C6—C7—H7B	110.9 (11)	C10—C15—H15	118.5 (10)

C9—N1—N2—C8	172.48 (12)	C6—C7—C8—O1	−49.3 (2)
C6—C1—C2—C3	−0.4 (3)	C6—C7—C8—N2	131.47 (14)
C1—C2—C3—C4	0.0 (3)	N2—N1—C9—C10	174.13 (11)
C1—C2—C3—F1	−179.98 (16)	N1—C9—C10—C11	166.80 (12)
C2—C3—C4—C5	0.5 (3)	N1—C9—C10—C15	−14.1 (2)
F1—C3—C4—C5	−179.50 (14)	C15—C10—C11—C12	0.0 (2)
C3—C4—C5—C6	−0.6 (2)	C9—C10—C11—C12	179.11 (13)
C2—C1—C6—C5	0.3 (2)	C10—C11—C12—C13	0.3 (2)
C2—C1—C6—C7	−179.85 (14)	C11—C12—C13—F2	178.96 (15)
C4—C5—C6—C1	0.2 (2)	C11—C12—C13—C14	−0.3 (3)
C4—C5—C6—C7	−179.62 (13)	F2—C13—C14—C15	−179.36 (15)
C1—C6—C7—C8	−102.93 (16)	C12—C13—C14—C15	−0.1 (3)
C5—C6—C7—C8	76.90 (18)	C13—C14—C15—C10	0.5 (2)
N1—N2—C8—O1	−9.9 (2)	C11—C10—C15—C14	−0.4 (2)
N1—N2—C8—C7	169.41 (12)	C9—C10—C15—C14	−179.50 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···O1ⁱ	0.892 (15)	2.013 (15)	2.8841 (14)	165.2 (14)
C4—H4···O1ⁱⁱ	0.92 (2)	2.47 (2)	3.370 (2)	168 (2)
C1—H1···Cg1ⁱⁱⁱ	0.98 (2)	2.92 (2)	3.7025 (18)	138.0 (15)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂F₂N₂O
M_r	274.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.8754 (15), 12.5349 (13), 7.7093 (8)
β (°)	93.566 (2)
V (Å³)	1338.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.85 × 0.26 × 0.12

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.915, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	17153, 4415, 2586
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.734

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.153, 1.02
No. of reflections	4415
No. of parameters	229
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···O1ⁱ	0.892 (15)	2.013 (15)	2.8841 (14)	165.2 (14)
C4—H4···O1ⁱⁱ	0.92 (2)	2.47 (2)	3.370 (2)	168 (2)
C1—H1···Cg1ⁱⁱⁱ	0.98 (2)	2.92 (2)	3.7025 (18)	138.0 (15)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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