N'-(4-Fluoro-benzyl-idene)-2-(4-fluoro-phen-yl)acetohydrazide.

In the title compound, C(15)H(12)F(2)N(2)O, 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, mol-ecules are connected by strong N-H⋯O and weak C-H⋯O hydrogen bonds, forming supra-molecular chains along the c axis. The structure is consolidated by π-π [centroid-centroid separation = 3.6579 (10) Å] and C-H⋯π inter-actions.

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 = 274.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.153

S = 1.02

4415 reflections

229 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039845/hb6416sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811039845/hb6416Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12F2N2O	F(000) = 568
Mr = 274.27	Dx = 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

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

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(Fo2) + (0.0752P)2 + 0.0834P] where P = (Fo2 + 2Fc2)/3
4415 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .