Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045631/at2398sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045631/at2398Isup2.hkl |
CCDC reference: 663820
The title compound (I) was synthesized according to the reported method (Sreekumar et al., 2003) with a yield of 85% (Fig. 4). The compound was purified by recrystallization from ethanol. The initially formed 3-{(E)-[2-(trifluoromethyl)phenyl]diazenyl}pentane-2,4-dione underwent enolization to form pentane-2,3,4-trione 3-{[2-(trifluoromethyl)phenyl] hydrazone}. The crystal growth was done in a 8:2 mixture of toluene–acetone by slow evaporation technique [m.p.: 373–375 K]. Analysis for C12H11F3N2O2: Found (Calculated): C 52.75 (52.94), H 4.20 (4.04), N 10.39% (10.29%).
All C-bound H atoms were refined using the riding model approximation with d(C—H) = 0.93 for aromatic and d(C—H) = 0.96 for methyl C—H [Uiso(H) = 1.2 or 1.5Ueq(parent atom)]. N-bound H atom was located in Fourier difference map and refined freely due to its taking part in H-bond.
The title compound is used as an intermediate in the synthesis of acetyl cinnoline derivative. Cinnoline derivatives are known for their pharmacological activities (Narayana et al., 2006). The title compound synthesized by coupling 2-trifluoro methyl benzene diazoniumchloride with acetyl acetone [Fig. 4] which further underwent cyclization to yield cinnoline derivative. Recently, fluorinated organic compounds have attracted attention due to the ability of fluorine to act as polar hydrogen or hydroxyl mimic. Therefore, substitution of hydrogen by fluorine has been a strategy in designing molecules for biological activity studies (Filler & Kabayashi, 1992). Owing to the importance of title compound (I), the present paper reports the synthesis and crystal structure of the title compound.
Phenylhydrazono-1,3-diones can exist in four tautomeric forms [Fig. 3]. Our investigations show that, in the solid state, the molecular structure of (I) adopts the keto-hydrazo B form with three intramolecular hydrogen bonds (Fig. 1). This is also indicated by the N—N and C—N bond lengths (Table 1). In (I), the C1—N1, C10—N2 and N1—N2 bond lengths are 1.402 (2) Å, 1.310 (2) Å and 1.3161 (19) Å, respectively. These bonds lengths are common feature of similar systems (Odabaşoğlu et al., 2005a,b; Alpaslan et al., 2005a,b; Alpaslan et al., 2005; Alpaslan, Özdamar et al., 2006; Alpaslan, Odabaşoğlu et al., 2006; Alpaslan et al., 2007a,b).
The N1—N2 single bond of 1.3161 (19) Å is shorter than that observed in 1,2-bis-[1-(3-pyridyl)3-methyltriazen-3-yl]ethane [1.326 (3) Å; Vaughan et al., 2004] and other triazines (Pottie et al., 1998; Hooper et al., 1998). This shortening in the hydrazone group is consistent with the resonance structures shown in Fig. 3, which give to the N1—N2 bond some double-bond character.
The crystal packing is stabilized N—H···F, N—H···O intramolecular and C—H···O, C—H···F intermolecular hydrogen bonds. These hydrogen bonds generate edge-fussed R44(13)S(6)S(6)S(6)R33(20) ring motifs in xz plane (Fig. 2) (Etter, 1990). Except the four protons of methyl groups and two fluour atoms of three fluourmethyl group, all atoms are almost in the same plane and the dihedral angle between the aromatic ring and N1/N2/C10/C9 plane in substituted group is 3.77 (8)°. There is no C—H···π and π···π interaction in crystal packing.
For related structures, see: 2-bromo-N'-[(E)-4-hydroxybenzylidene]-5-methoxybenzohydrazide (Sarojini et al., 2007); bis{4-[(2-hydroxybenzylidine)hydrazino]-8-(trifluoro-methyl)quinolinium}sulfate tetrahydrate (Yathirajan et al., 2007); ethyl 4-chloro-2-[(2-nitrophenyl)hydrazono]-3-oxobutyrate (Odabaşoğlu et al., 2005a); ethyl 4-chloro-2-[(4-nitrophenyl)hydrazono]-3-oxobutyrate (Odabaşoğlu et al., 2005b). For related literature, see: Filler & Kabayashi (1992); Sreekumar et al. (2003); Narayana et al. (2006); Alpaslan et al., 2005a,b; Alpaslan et al., 2005; Alpaslan, Özdamar et al., 2006; Alpaslan, Odabaşoğlu et al., 2006; Alpaslan et al. (2007a,b); Etter (1990); Hooper et al. (1998); Pottie et al. (1998); Vaughan et al. (2004).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C12H11F3N2O2 | F(000) = 560 |
Mr = 272.23 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 15716 reflections |
a = 8.2941 (4) Å | θ = 1.9–28.0° |
b = 7.0893 (5) Å | µ = 0.13 mm−1 |
c = 22.2665 (11) Å | T = 296 K |
β = 109.545 (4)° | Prism, yellow |
V = 1233.81 (12) Å3 | 0.65 × 0.57 × 0.44 mm |
Z = 4 |
Stoe IPDS-2 diffractometer | 2433 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1919 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.040 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
ω scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.925, Tmax = 0.952 | l = −27→27 |
15716 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0769P)2 + 0.1968P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
2433 reflections | Δρmax = 0.33 e Å−3 |
179 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (3) |
C12H11F3N2O2 | V = 1233.81 (12) Å3 |
Mr = 272.23 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.2941 (4) Å | µ = 0.13 mm−1 |
b = 7.0893 (5) Å | T = 296 K |
c = 22.2665 (11) Å | 0.65 × 0.57 × 0.44 mm |
β = 109.545 (4)° |
Stoe IPDS-2 diffractometer | 2433 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1919 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.952 | Rint = 0.040 |
15716 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.33 e Å−3 |
2433 reflections | Δρmin = −0.22 e Å−3 |
179 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4714 (2) | 0.2443 (2) | 0.48094 (7) | 0.0492 (4) | |
C2 | 0.6472 (2) | 0.2478 (2) | 0.49847 (8) | 0.0564 (4) | |
H2 | 0.7125 | 0.2667 | 0.5410 | 0.068* | |
C3 | 0.7275 (3) | 0.2239 (3) | 0.45425 (10) | 0.0658 (5) | |
H3 | 0.8463 | 0.2264 | 0.4670 | 0.079* | |
C4 | 0.6326 (3) | 0.1961 (3) | 0.39106 (9) | 0.0674 (5) | |
H4 | 0.6872 | 0.1793 | 0.3611 | 0.081* | |
C5 | 0.4580 (3) | 0.1934 (3) | 0.37252 (8) | 0.0625 (5) | |
H5 | 0.3944 | 0.1747 | 0.3298 | 0.075* | |
C6 | 0.3743 (2) | 0.2181 (2) | 0.41629 (8) | 0.0530 (4) | |
C7 | 0.1812 (3) | 0.2184 (3) | 0.39347 (8) | 0.0637 (5) | |
C8 | 0.1589 (3) | 0.2857 (4) | 0.67265 (11) | 0.0830 (7) | |
H8A | 0.0433 | 0.2401 | 0.6574 | 0.100* | |
H8B | 0.1613 | 0.4092 | 0.6906 | 0.100* | |
H8C | 0.2283 | 0.2015 | 0.7047 | 0.100* | |
C9 | 0.2271 (2) | 0.2953 (3) | 0.61862 (9) | 0.0603 (5) | |
C10 | 0.4125 (2) | 0.3127 (2) | 0.63042 (8) | 0.0513 (4) | |
C11 | 0.5375 (2) | 0.3573 (3) | 0.69423 (8) | 0.0580 (5) | |
C12 | 0.7209 (3) | 0.3113 (4) | 0.70645 (10) | 0.0794 (6) | |
H12A | 0.7591 | 0.3724 | 0.6751 | 0.095* | |
H12B | 0.7338 | 0.1773 | 0.7039 | 0.095* | |
H12C | 0.7881 | 0.3545 | 0.7482 | 0.095* | |
N1 | 0.3891 (2) | 0.2659 (2) | 0.52622 (7) | 0.0523 (4) | |
N2 | 0.48311 (18) | 0.29271 (19) | 0.58622 (6) | 0.0504 (4) | |
O1 | 0.12893 (18) | 0.2806 (3) | 0.56407 (7) | 0.0824 (5) | |
O2 | 0.49197 (19) | 0.4327 (2) | 0.73475 (6) | 0.0792 (5) | |
F1 | 0.1151 (2) | 0.2002 (3) | 0.33166 (6) | 0.1288 (7) | |
F2 | 0.11712 (17) | 0.0876 (2) | 0.42020 (8) | 0.1040 (5) | |
F3 | 0.12016 (18) | 0.3783 (2) | 0.40798 (8) | 0.1052 (5) | |
H1 | 0.277 (3) | 0.266 (3) | 0.5163 (10) | 0.073 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0549 (9) | 0.0472 (8) | 0.0424 (8) | −0.0006 (7) | 0.0123 (7) | 0.0008 (6) |
C2 | 0.0553 (10) | 0.0638 (10) | 0.0458 (9) | −0.0007 (8) | 0.0109 (7) | −0.0002 (7) |
C3 | 0.0573 (11) | 0.0793 (13) | 0.0619 (11) | 0.0006 (9) | 0.0215 (9) | 0.0030 (9) |
C4 | 0.0770 (14) | 0.0767 (12) | 0.0549 (10) | 0.0007 (10) | 0.0308 (9) | 0.0011 (9) |
C5 | 0.0763 (13) | 0.0656 (11) | 0.0428 (8) | −0.0012 (9) | 0.0161 (8) | −0.0008 (8) |
C6 | 0.0583 (10) | 0.0537 (9) | 0.0420 (8) | −0.0020 (7) | 0.0101 (7) | 0.0009 (6) |
C7 | 0.0643 (11) | 0.0732 (12) | 0.0431 (9) | −0.0004 (9) | 0.0040 (8) | 0.0012 (8) |
C8 | 0.0678 (13) | 0.1169 (19) | 0.0717 (14) | −0.0016 (12) | 0.0332 (11) | 0.0008 (12) |
C9 | 0.0582 (10) | 0.0658 (11) | 0.0568 (10) | 0.0031 (8) | 0.0193 (8) | −0.0002 (8) |
C10 | 0.0531 (9) | 0.0557 (9) | 0.0437 (8) | 0.0006 (7) | 0.0145 (7) | 0.0014 (7) |
C11 | 0.0640 (11) | 0.0647 (10) | 0.0431 (8) | −0.0043 (8) | 0.0152 (8) | 0.0035 (7) |
C12 | 0.0618 (12) | 0.1099 (17) | 0.0566 (11) | −0.0018 (11) | 0.0067 (9) | −0.0074 (11) |
N1 | 0.0498 (8) | 0.0624 (9) | 0.0411 (7) | −0.0011 (6) | 0.0103 (6) | −0.0028 (6) |
N2 | 0.0545 (8) | 0.0528 (8) | 0.0406 (7) | −0.0012 (6) | 0.0115 (6) | −0.0007 (5) |
O1 | 0.0520 (8) | 0.1283 (14) | 0.0622 (8) | −0.0022 (8) | 0.0131 (7) | −0.0069 (8) |
O2 | 0.0871 (10) | 0.1029 (12) | 0.0496 (7) | −0.0062 (8) | 0.0253 (7) | −0.0131 (7) |
F1 | 0.0765 (9) | 0.237 (2) | 0.0541 (7) | −0.0064 (11) | −0.0032 (7) | −0.0179 (10) |
F2 | 0.0668 (8) | 0.1121 (12) | 0.1195 (12) | −0.0202 (7) | 0.0130 (8) | 0.0208 (9) |
F3 | 0.0728 (9) | 0.1024 (11) | 0.1225 (12) | 0.0224 (7) | 0.0087 (8) | −0.0039 (9) |
C1—C2 | 1.378 (3) | C8—C9 | 1.493 (3) |
C1—N1 | 1.402 (2) | C8—H8A | 0.9600 |
C1—C6 | 1.407 (2) | C8—H8B | 0.9600 |
C2—C3 | 1.371 (3) | C8—H8C | 0.9600 |
C2—H2 | 0.9300 | C9—O1 | 1.220 (2) |
C3—C4 | 1.377 (3) | C9—C10 | 1.476 (3) |
C3—H3 | 0.9300 | C10—N2 | 1.310 (2) |
C4—C5 | 1.367 (3) | C10—C11 | 1.486 (2) |
C4—H4 | 0.9300 | C11—O2 | 1.213 (2) |
C5—C6 | 1.384 (3) | C11—C12 | 1.489 (3) |
C5—H5 | 0.9300 | C12—H12A | 0.9600 |
C6—C7 | 1.509 (3) | C12—H12B | 0.9600 |
C7—F1 | 1.306 (2) | C12—H12C | 0.9600 |
C7—F2 | 1.307 (2) | N1—N2 | 1.3161 (19) |
C7—F3 | 1.325 (2) | N1—H1 | 0.88 (2) |
C2—C1—N1 | 121.20 (15) | C9—C8—H8B | 109.5 |
C2—C1—C6 | 118.76 (16) | H8A—C8—H8B | 109.5 |
N1—C1—C6 | 120.04 (16) | C9—C8—H8C | 109.5 |
C3—C2—C1 | 121.10 (17) | H8A—C8—H8C | 109.5 |
C3—C2—H2 | 119.4 | H8B—C8—H8C | 109.5 |
C1—C2—H2 | 119.4 | O1—C9—C10 | 119.55 (17) |
C2—C3—C4 | 120.17 (19) | O1—C9—C8 | 119.46 (18) |
C2—C3—H3 | 119.9 | C10—C9—C8 | 120.91 (17) |
C4—C3—H3 | 119.9 | N2—C10—C9 | 123.91 (15) |
C5—C4—C3 | 119.73 (18) | N2—C10—C11 | 113.40 (15) |
C5—C4—H4 | 120.1 | C9—C10—C11 | 122.69 (15) |
C3—C4—H4 | 120.1 | O2—C11—C10 | 120.92 (17) |
C4—C5—C6 | 121.07 (17) | O2—C11—C12 | 120.94 (17) |
C4—C5—H5 | 119.5 | C10—C11—C12 | 118.12 (16) |
C6—C5—H5 | 119.5 | C11—C12—H12A | 109.5 |
C5—C6—C1 | 119.16 (17) | C11—C12—H12B | 109.5 |
C5—C6—C7 | 119.25 (16) | H12A—C12—H12B | 109.5 |
C1—C6—C7 | 121.58 (15) | C11—C12—H12C | 109.5 |
F1—C7—F2 | 108.57 (18) | H12A—C12—H12C | 109.5 |
F1—C7—F3 | 106.34 (18) | H12B—C12—H12C | 109.5 |
F2—C7—F3 | 104.40 (19) | N2—N1—C1 | 118.68 (15) |
F1—C7—C6 | 112.27 (17) | N2—N1—H1 | 118.2 (14) |
F2—C7—C6 | 113.16 (16) | C1—N1—H1 | 123.1 (14) |
F3—C7—C6 | 111.60 (16) | C10—N2—N1 | 121.07 (15) |
C9—C8—H8A | 109.5 | ||
N1—C1—C2—C3 | 179.00 (16) | C5—C6—C7—F3 | −121.40 (19) |
C6—C1—C2—C3 | −0.8 (3) | C1—C6—C7—F3 | 57.9 (2) |
C1—C2—C3—C4 | 0.1 (3) | O1—C9—C10—N2 | −7.9 (3) |
C2—C3—C4—C5 | 0.3 (3) | C8—C9—C10—N2 | 169.00 (19) |
C3—C4—C5—C6 | 0.0 (3) | O1—C9—C10—C11 | 171.41 (18) |
C4—C5—C6—C1 | −0.7 (3) | C8—C9—C10—C11 | −11.7 (3) |
C4—C5—C6—C7 | 178.65 (18) | N2—C10—C11—O2 | 158.23 (18) |
C2—C1—C6—C5 | 1.1 (2) | C9—C10—C11—O2 | −21.1 (3) |
N1—C1—C6—C5 | −178.74 (15) | N2—C10—C11—C12 | −20.2 (2) |
C2—C1—C6—C7 | −178.23 (16) | C9—C10—C11—C12 | 160.42 (18) |
N1—C1—C6—C7 | 2.0 (2) | C2—C1—N1—N2 | 1.1 (2) |
C5—C6—C7—F1 | −2.1 (3) | C6—C1—N1—N2 | −179.10 (14) |
C1—C6—C7—F1 | 177.18 (18) | C9—C10—N2—N1 | 4.1 (3) |
C5—C6—C7—F2 | 121.19 (19) | C11—C10—N2—N1 | −175.25 (14) |
C1—C6—C7—F2 | −59.5 (2) | C1—N1—N2—C10 | −179.68 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 (2) | 1.88 (2) | 2.568 (2) | 133.8 (19) |
N1—H1···F3 | 0.88 (2) | 2.46 (2) | 2.935 (2) | 114.4 (17) |
N1—H1···F2 | 0.88 (2) | 2.46 (2) | 2.949 (2) | 115.9 (17) |
C3—H3···O1i | 0.93 | 2.63 | 3.432 (3) | 145 |
C5—H5···O2ii | 0.93 | 2.62 | 3.297 (2) | 130 |
C12—H12C···F1iii | 0.96 | 2.75 | 3.517 (2) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H11F3N2O2 |
Mr | 272.23 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 8.2941 (4), 7.0893 (5), 22.2665 (11) |
β (°) | 109.545 (4) |
V (Å3) | 1233.81 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.65 × 0.57 × 0.44 |
Data collection | |
Diffractometer | Stoe IPDS2 |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.925, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15716, 2433, 1919 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.145, 1.10 |
No. of reflections | 2433 |
No. of parameters | 179 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.22 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 (2) | 1.88 (2) | 2.568 (2) | 133.8 (19) |
N1—H1···F3 | 0.88 (2) | 2.46 (2) | 2.935 (2) | 114.4 (17) |
N1—H1···F2 | 0.88 (2) | 2.46 (2) | 2.949 (2) | 115.9 (17) |
C3—H3···O1i | 0.93 | 2.63 | 3.432 (3) | 144.6 |
C5—H5···O2ii | 0.93 | 2.62 | 3.297 (2) | 130.2 |
C12—H12C···F1iii | 0.96 | 2.75 | 3.517 (2) | 136.9 |
Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z−1/2; (iii) x+1, −y+1/2, z+1/2. |
The title compound is used as an intermediate in the synthesis of acetyl cinnoline derivative. Cinnoline derivatives are known for their pharmacological activities (Narayana et al., 2006). The title compound synthesized by coupling 2-trifluoro methyl benzene diazoniumchloride with acetyl acetone [Fig. 4] which further underwent cyclization to yield cinnoline derivative. Recently, fluorinated organic compounds have attracted attention due to the ability of fluorine to act as polar hydrogen or hydroxyl mimic. Therefore, substitution of hydrogen by fluorine has been a strategy in designing molecules for biological activity studies (Filler & Kabayashi, 1992). Owing to the importance of title compound (I), the present paper reports the synthesis and crystal structure of the title compound.
Phenylhydrazono-1,3-diones can exist in four tautomeric forms [Fig. 3]. Our investigations show that, in the solid state, the molecular structure of (I) adopts the keto-hydrazo B form with three intramolecular hydrogen bonds (Fig. 1). This is also indicated by the N—N and C—N bond lengths (Table 1). In (I), the C1—N1, C10—N2 and N1—N2 bond lengths are 1.402 (2) Å, 1.310 (2) Å and 1.3161 (19) Å, respectively. These bonds lengths are common feature of similar systems (Odabaşoğlu et al., 2005a,b; Alpaslan et al., 2005a,b; Alpaslan et al., 2005; Alpaslan, Özdamar et al., 2006; Alpaslan, Odabaşoğlu et al., 2006; Alpaslan et al., 2007a,b).
The N1—N2 single bond of 1.3161 (19) Å is shorter than that observed in 1,2-bis-[1-(3-pyridyl)3-methyltriazen-3-yl]ethane [1.326 (3) Å; Vaughan et al., 2004] and other triazines (Pottie et al., 1998; Hooper et al., 1998). This shortening in the hydrazone group is consistent with the resonance structures shown in Fig. 3, which give to the N1—N2 bond some double-bond character.
The crystal packing is stabilized N—H···F, N—H···O intramolecular and C—H···O, C—H···F intermolecular hydrogen bonds. These hydrogen bonds generate edge-fussed R44(13)S(6)S(6)S(6)R33(20) ring motifs in xz plane (Fig. 2) (Etter, 1990). Except the four protons of methyl groups and two fluour atoms of three fluourmethyl group, all atoms are almost in the same plane and the dihedral angle between the aromatic ring and N1/N2/C10/C9 plane in substituted group is 3.77 (8)°. There is no C—H···π and π···π interaction in crystal packing.