(E)-1-(4-Methyl­phen­yl)ethanone [8-(trifluoro­meth­yl)quinolin-4-yl]hydrazone

Dutkiewicz, G.; Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.; Kubicki, M.

doi:10.1107/S1600536810009475

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o874

doi:10.1107/S1600536810009475

Open

access

(E)-1-(4-Methylphenyl)ethanone [8-(trifluoromethyl)quinolin-4-yl]hydrazone

Grzegorz Dutkiewicz,^a Anil N. Mayekar,^b H. S. Yathirajan,^b B. Narayana ^c and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 5 March 2010; accepted 12 March 2010; online 20 March 2010)

In the title compound, C₁₉H₁₆F₃N₃, the dihedral angle between the naphthalene and quinoline ring systems is 14.58 (8)°. The hydrazone C—N—N=C—C chain is in an extended conformation and its mean plane is nearly coplanar with the quinoline plane [dihedral angle = 3.45 (9)°]. The bond angles within the phenyl ring show the almost additive influence of the two para substituents. In the crystal, weak π–π [centroid–centroid distances = 3.779 (2) and 3.718 (1) Å] and C—H⋯F directional interactions join the molecules into centrosymmetric dimers, which are further connected into infinite zigzag chains propagating along a.

Related literature

For second-order non-linear activity, see: Serbutoviez et al. (1995 ). For related structures, see: Jasinski et al. (2008 ); Yathirajan et al. (2007 ). For a description fo the Cambridge Structural Database, see: Allen (2002 ). For bond angles in mono-substituted phenyl rings, see: Domenicano (1988 $[Domenicano, A. (1988). Stereochemical Applications of Gas-Phase Electron Diffraction, edited by I. Hargittai & M. Hargittai, pp. 281-324. New York: VCH.]$ ).

Experimental

Crystal data

C₁₉H₁₆F₃N₃
M_r = 343.35
Monoclinic, P 2₁ /c
a = 8.2811 (9) Å
b = 14.8443 (15) Å
c = 13.5325 (15) Å
β = 90.601 (9)°
V = 1663.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.4 × 0.15 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 large Be window diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, UK.]$ ) T_min = 0.737, T_max = 1.000
8893 measured reflections
3391 independent reflections
2248 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.156
S = 1.12
3391 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F91Aⁱ	0.93	2.50	3.336 (2)	150
C14—H14C⋯F91Cⁱⁱ	0.96	2.55	3.384 (2)	146
C17—H17⋯F91Cⁱⁱⁱ	0.93	2.54	3.425 (3)	160
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z; (iii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, UK.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009475/dn2546sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009475/dn2546Isup2.hkl

checkCIF report

Comment top

Hydrazones constitute a class of compounds of general formula R₁R₂C═ N—NR₃R₄. Serbutoviez et al. (1995) have shown that some diaryl hydrazone derivatives show efficient second-order nonlinear activity. They connected the tendency to crystallize in Λ-shaped pairs with the possibility of the application for the frequency conversion but not for electrooptics. Here we present the structure of (E)-1-(4-methylphenyl)ethanone [8-(trifluoromethyl)quinolin-4-yl]hydrazone (I, Scheme 1); the crystal structures of two salts of similar (quinoline - phenyl) hydrazones have been reported recently: bis{4-[(2-hydroxybenzylidine)hydrazino]- 8-(trifluoromethyl)quinolinium} sulfate tetrahydrate (Yathirajan et al., 2007) and bis{4-[(Z)—N'-(4-hydroxybenzylidene)- hydrazino]-8-(trifluoromethyl)- quinolinium} sulfate dihydrate (Jasinski et al., 2008).

The overall conformation of the molecules of I can be described by the values of dihedral angles between the three planar fragments: the quinoline ring system (hereinafter A will denote pyridine ring, B - trifluoromethylphenyl ring, planar within 0.0076 (14) Å), the central extended C—N—N═ C—C chain (maximum deviation from the least-squares plane of 0.0158 (12) Å), and the phenyl ring (C, maximum deviation 0.021 (2) Å). While the first two fragments are almost coplanar, dihedral angle between the planes is only 3.45 (9)°, this fragment is significantly, by 14.5 (1)°, twisted with respect to the phenyl ring plane. Such conformation is rather typical; for 186 fragments found in 155 similar compunds (Ar₁—N—N═C—Ar₂) found in the Cambridge Structual Database [CSD, Conquest 5.31; Allen, 2002] the Ar₁ plane is close to coplanarity with the central chain (mean value 5.9 (3)°, maximum 18.7°), while it is more twisted with respect to Ar₂ plane (mean 17 (2)°, 33 examples of angles larger than 30°). The bond length pattern within the chain reflects the more single/double character of certain bonds. The bond angles within the phenyl ring are influenced by the presence of substituents; as expected for p-substitution, the influences are almost additive. The sum of values given by Domenicano (1988) or found in the CSD for mono-substituted phenyl rings are very close to the actual values in (I).

In the crystal the molecules are connected into dimers by π–π interactions: centroid-to-centroid distance between rings A and B (2-x,-y,-z) is 3.779 (2)Å with an offset of 22.1°, which gives the interplanar distance of 3.509Å (mean value). Distance between centroids of rings B and B(2-x,-y,-z) is 3.718 (1) Å, with interplanar distance of 3.516Å resulting in an offset of 19.0°. These dimers, in which there are additional C—H···F (Table 1) contacts (Fig. 2), are further connected into zig-zag chains (Λ-shaped) along a direction. It might be noted, that the N—H hydrogen atom is so hidden by the neighboring C6—H6 and C14 methyl hydrogen atoms that it can not be involved in any intermolecular interactions.

Related literature top

Experimental top

A solution of 4-hydrazino-8-(trifluoromethyl)quinoline (2.2 g, 10 mmole) and 4-methyl-acetophenone (10.2 mmole ) in 10 ml of ethanol was refluxed for 24 hrs under nitrogen atmosphere and in absence of light. The reaction mass was then cooled and the solid separated was collected by filtration and recrystallized from ethanol. M.P.: 449-451 K. Analysis found : C 66.41, H 4.67, N 12.20; C₁₉H₁₆F₃N₃ requires : C 66.48, H 4.70, N 12.24%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of the compound I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.
	Fig. 2. The centrosymmetric dimer of molecules I; π–π and C—H···F contacts are shown as dashed lines. are shown as dashed lines.

(E)-1-(4-Methylphenyl)ethanone [8-(trifluoromethyl)quinolin-4-yl]hydrazone top

Crystal data top

C₁₉H₁₆F₃N₃	F(000) = 712
M_r = 343.35	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4730 reflections
a = 8.2811 (9) Å	θ = 3.0–28.0°
b = 14.8443 (15) Å	µ = 0.11 mm⁻¹
c = 13.5325 (15) Å	T = 295 K
β = 90.601 (9)°	Prism, yellow
V = 1663.4 (3) Å³	0.4 × 0.15 × 0.15 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire2 large Be window diffractometer	3391 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 8.1929 pixels mm^-1	θ_max = 28.1°, θ_min = 3.0°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→19
T_min = 0.737, T_max = 1.000	l = −17→13
8893 measured reflections

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0897P)²] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
3391 reflections	Δρ_max = 0.25 e Å⁻³
229 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (3)

Crystal data top

C₁₉H₁₆F₃N₃	V = 1663.4 (3) Å³
M_r = 343.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2811 (9) Å	µ = 0.11 mm⁻¹
b = 14.8443 (15) Å	T = 295 K
c = 13.5325 (15) Å	0.4 × 0.15 × 0.15 mm
β = 90.601 (9)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 large Be window diffractometer	3391 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2248 reflections with I > 2σ(I)
T_min = 0.737, T_max = 1.000	R_int = 0.021
8893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.12	Δρ_max = 0.25 e Å⁻³
3391 reflections	Δρ_min = −0.19 e Å⁻³
229 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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.83992 (19)	0.01946 (10)	0.20074 (10)	0.0513 (4)
C2	0.7602 (3)	−0.05642 (13)	0.20928 (14)	0.0597 (6)
H2	0.7546	−0.0817	0.2721	0.072*
C3	0.6830 (2)	−0.10262 (12)	0.13230 (13)	0.0537 (5)
H3	0.6293	−0.1565	0.1444	0.064*
C4	0.68734 (19)	−0.06746 (11)	0.03860 (12)	0.0401 (4)
C5	0.77200 (18)	0.01539 (10)	0.02401 (11)	0.0370 (4)
C6	0.7863 (2)	0.05794 (11)	−0.06808 (13)	0.0474 (5)
H6	0.7370	0.0323	−0.1233	0.057*
C7	0.8702 (2)	0.13543 (12)	−0.07816 (15)	0.0573 (5)
H7	0.8792	0.1620	−0.1401	0.069*
C8	0.9435 (2)	0.17588 (12)	0.00411 (16)	0.0553 (5)
H8	1.0003	0.2295	−0.0034	0.066*
C9	0.93256 (19)	0.13729 (11)	0.09527 (14)	0.0430 (4)
C91	1.0141 (2)	0.18041 (12)	0.18190 (16)	0.0564 (5)
F91A	0.91479 (15)	0.20118 (9)	0.25506 (10)	0.0827 (5)
F91B	1.09032 (17)	0.25657 (8)	0.15776 (12)	0.0910 (5)
F91C	1.12986 (14)	0.12807 (8)	0.22230 (9)	0.0708 (4)
C10	0.84643 (19)	0.05542 (10)	0.10817 (12)	0.0388 (4)
N11	0.61492 (17)	−0.10952 (9)	−0.04049 (11)	0.0469 (4)
H11	0.6160	−0.0855	−0.0983	0.056*
N12	0.54053 (17)	−0.19105 (9)	−0.02519 (10)	0.0451 (4)
C13	0.47706 (18)	−0.23051 (12)	−0.10088 (13)	0.0409 (4)
C14	0.4800 (2)	−0.19314 (13)	−0.20397 (13)	0.0536 (5)
H14A	0.4451	−0.1315	−0.2031	0.080*
H14B	0.4088	−0.2277	−0.2457	0.080*
H14C	0.5879	−0.1964	−0.2290	0.080*
C15	0.39938 (19)	−0.31859 (12)	−0.08073 (12)	0.0426 (4)
C16	0.3532 (3)	−0.37659 (15)	−0.15437 (16)	0.0757 (7)
H16	0.3689	−0.3603	−0.2199	0.091*
C17	0.2841 (3)	−0.45844 (17)	−0.13344 (18)	0.0938 (9)
H17	0.2546	−0.4961	−0.1855	0.113*
C18	0.2571 (3)	−0.48652 (14)	−0.03884 (16)	0.0652 (6)
C19	0.2963 (3)	−0.42716 (16)	0.03489 (17)	0.0790 (7)
H19	0.2747	−0.4424	0.1001	0.095*
C20	0.3673 (3)	−0.34517 (15)	0.01459 (15)	0.0711 (6)
H20	0.3942	−0.3069	0.0666	0.085*
C21	0.1827 (4)	−0.57785 (17)	−0.0168 (2)	0.0937 (8)
H21A	0.1198	−0.5974	−0.0728	0.141*
H21B	0.1145	−0.5730	0.0399	0.141*
H21C	0.2669	−0.6208	−0.0036	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0716 (10)	0.0439 (9)	0.0383 (9)	−0.0069 (8)	0.0033 (7)	−0.0045 (7)
C2	0.0930 (14)	0.0510 (12)	0.0352 (11)	−0.0162 (11)	0.0069 (10)	0.0043 (8)
C3	0.0784 (13)	0.0422 (10)	0.0407 (11)	−0.0182 (9)	0.0096 (9)	0.0018 (8)
C4	0.0468 (9)	0.0359 (9)	0.0376 (10)	−0.0010 (7)	0.0063 (7)	−0.0037 (7)
C5	0.0413 (8)	0.0325 (9)	0.0374 (9)	0.0042 (7)	0.0063 (7)	0.0002 (7)
C6	0.0576 (11)	0.0425 (10)	0.0419 (11)	−0.0032 (8)	0.0007 (8)	0.0063 (8)
C7	0.0696 (12)	0.0489 (11)	0.0535 (12)	−0.0040 (10)	0.0015 (10)	0.0173 (9)
C8	0.0566 (11)	0.0326 (9)	0.0768 (15)	−0.0044 (8)	0.0033 (10)	0.0108 (9)
C9	0.0436 (9)	0.0305 (9)	0.0550 (11)	0.0029 (7)	0.0042 (8)	−0.0027 (8)
C91	0.0586 (11)	0.0383 (10)	0.0723 (14)	−0.0024 (9)	0.0007 (11)	−0.0079 (10)
F91A	0.0791 (8)	0.0770 (9)	0.0921 (10)	−0.0038 (6)	0.0074 (7)	−0.0479 (7)
F91B	0.1055 (10)	0.0536 (8)	0.1134 (11)	−0.0350 (7)	−0.0218 (8)	−0.0004 (7)
F91C	0.0662 (7)	0.0711 (8)	0.0748 (9)	0.0030 (6)	−0.0153 (6)	−0.0064 (6)
C10	0.0440 (9)	0.0318 (9)	0.0407 (10)	0.0044 (7)	0.0061 (7)	−0.0031 (7)
N11	0.0603 (9)	0.0418 (9)	0.0385 (8)	−0.0095 (7)	0.0008 (7)	0.0017 (6)
N12	0.0516 (8)	0.0389 (8)	0.0451 (9)	−0.0074 (6)	0.0035 (7)	−0.0030 (7)
C13	0.0398 (9)	0.0432 (10)	0.0398 (10)	0.0019 (7)	0.0027 (7)	−0.0035 (8)
C14	0.0549 (10)	0.0589 (12)	0.0468 (11)	−0.0128 (9)	−0.0026 (9)	0.0019 (9)
C15	0.0420 (9)	0.0446 (10)	0.0412 (10)	−0.0023 (7)	−0.0002 (7)	−0.0038 (8)
C16	0.1163 (18)	0.0696 (15)	0.0415 (12)	−0.0364 (14)	0.0040 (12)	−0.0073 (10)
C17	0.151 (2)	0.0727 (16)	0.0582 (15)	−0.0566 (16)	0.0012 (15)	−0.0164 (12)
C18	0.0776 (13)	0.0546 (13)	0.0633 (14)	−0.0191 (11)	−0.0049 (11)	0.0019 (10)
C19	0.1223 (19)	0.0664 (15)	0.0481 (13)	−0.0332 (14)	−0.0083 (13)	0.0116 (11)
C20	0.1085 (17)	0.0601 (13)	0.0446 (12)	−0.0282 (12)	−0.0088 (12)	−0.0011 (10)
C21	0.123 (2)	0.0671 (16)	0.0911 (19)	−0.0361 (15)	−0.0111 (16)	0.0132 (13)

Geometric parameters (Å, º) top

N1—C2	1.311 (2)	N11—H11	0.8600
N1—C10	1.363 (2)	N12—C13	1.287 (2)
C2—C3	1.397 (3)	C13—C15	1.484 (2)
C2—H2	0.9300	C13—C14	1.502 (2)
C3—C4	1.372 (2)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—N11	1.372 (2)	C14—H14C	0.9600
C4—C5	1.430 (2)	C15—C16	1.369 (3)
C5—C6	1.403 (2)	C15—C20	1.377 (2)
C5—C10	1.420 (2)	C16—C17	1.374 (3)
C6—C7	1.351 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.367 (3)
C7—C8	1.398 (3)	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.368 (3)
C8—C9	1.364 (3)	C18—C21	1.520 (3)
C8—H8	0.9300	C19—C20	1.380 (3)
C9—C10	1.421 (2)	C19—H19	0.9300
C9—C91	1.491 (3)	C20—H20	0.9300
C91—F91A	1.330 (2)	C21—H21A	0.9600
C91—F91B	1.337 (2)	C21—H21B	0.9600
C91—F91C	1.345 (2)	C21—H21C	0.9600
N11—N12	1.3746 (18)

C2—N1—C10	116.24 (15)	N12—N11—H11	120.8
N1—C2—C3	125.66 (17)	C13—N12—N11	117.43 (14)
N1—C2—H2	117.2	N12—C13—C15	115.40 (15)
C3—C2—H2	117.2	N12—C13—C14	124.10 (16)
C4—C3—C2	119.09 (16)	C15—C13—C14	120.50 (15)
C4—C3—H3	120.5	C13—C14—H14A	109.5
C2—C3—H3	120.5	C13—C14—H14B	109.5
N11—C4—C3	122.16 (15)	H14A—C14—H14B	109.5
N11—C4—C5	119.64 (15)	C13—C14—H14C	109.5
C3—C4—C5	118.19 (15)	H14A—C14—H14C	109.5
C6—C5—C10	118.96 (15)	H14B—C14—H14C	109.5
C6—C5—C4	123.75 (15)	C16—C15—C20	116.53 (17)
C10—C5—C4	117.29 (14)	C16—C15—C13	122.61 (17)
C7—C6—C5	121.40 (17)	C20—C15—C13	120.85 (16)
C7—C6—H6	119.3	C15—C16—C17	121.3 (2)
C5—C6—H6	119.3	C15—C16—H16	119.3
C6—C7—C8	120.31 (17)	C17—C16—H16	119.3
C6—C7—H7	119.8	C18—C17—C16	122.4 (2)
C8—C7—H7	119.8	C18—C17—H17	118.8
C9—C8—C7	120.48 (16)	C16—C17—H17	118.8
C9—C8—H8	119.8	C17—C18—C19	116.54 (19)
C7—C8—H8	119.8	C17—C18—C21	121.8 (2)
C8—C9—C10	120.57 (17)	C19—C18—C21	121.7 (2)
C8—C9—C91	119.79 (16)	C18—C19—C20	121.4 (2)
C10—C9—C91	119.63 (16)	C18—C19—H19	119.3
F91A—C91—F91B	106.44 (16)	C20—C19—H19	119.3
F91A—C91—F91C	105.95 (17)	C15—C20—C19	121.71 (19)
F91B—C91—F91C	104.57 (15)	C15—C20—H20	119.1
F91A—C91—C9	113.97 (16)	C19—C20—H20	119.1
F91B—C91—C9	112.45 (17)	C18—C21—H21A	109.5
F91C—C91—C9	112.74 (15)	C18—C21—H21B	109.5
N1—C10—C5	123.52 (14)	H21A—C21—H21B	109.5
N1—C10—C9	118.20 (15)	C18—C21—H21C	109.5
C5—C10—C9	118.28 (15)	H21A—C21—H21C	109.5
C4—N11—N12	118.44 (14)	H21B—C21—H21C	109.5
C4—N11—H11	120.8

C10—N1—C2—C3	0.1 (3)	C4—C5—C10—C9	179.39 (13)
N1—C2—C3—C4	−0.4 (3)	C8—C9—C10—N1	179.64 (15)
C2—C3—C4—N11	179.62 (17)	C91—C9—C10—N1	0.8 (2)
C2—C3—C4—C5	0.2 (3)	C8—C9—C10—C5	−0.3 (2)
N11—C4—C5—C6	0.1 (2)	C91—C9—C10—C5	−179.13 (15)
C3—C4—C5—C6	179.55 (17)	C3—C4—N11—N12	−2.2 (2)
N11—C4—C5—C10	−179.21 (14)	C5—C4—N11—N12	177.15 (13)
C3—C4—C5—C10	0.2 (2)	C4—N11—N12—C13	−178.20 (15)
C10—C5—C6—C7	0.6 (3)	N11—N12—C13—C15	179.54 (13)
C4—C5—C6—C7	−178.79 (16)	N11—N12—C13—C14	0.2 (2)
C5—C6—C7—C8	−0.8 (3)	N12—C13—C15—C16	−167.60 (19)
C6—C7—C8—C9	0.6 (3)	C14—C13—C15—C16	11.8 (3)
C7—C8—C9—C10	0.0 (3)	N12—C13—C15—C20	13.7 (2)
C7—C8—C9—C91	178.86 (17)	C14—C13—C15—C20	−166.96 (18)
C8—C9—C91—F91A	122.12 (19)	C20—C15—C16—C17	−2.4 (4)
C10—C9—C91—F91A	−59.0 (2)	C13—C15—C16—C17	178.8 (2)
C8—C9—C91—F91B	0.9 (2)	C15—C16—C17—C18	0.2 (4)
C10—C9—C91—F91B	179.75 (15)	C16—C17—C18—C19	2.7 (4)
C8—C9—C91—F91C	−117.05 (18)	C16—C17—C18—C21	−179.1 (3)
C10—C9—C91—F91C	61.8 (2)	C17—C18—C19—C20	−3.3 (4)
C2—N1—C10—C5	0.4 (3)	C21—C18—C19—C20	178.5 (2)
C2—N1—C10—C9	−179.55 (16)	C16—C15—C20—C19	1.7 (3)
C6—C5—C10—N1	−179.90 (15)	C13—C15—C20—C19	−179.5 (2)
C4—C5—C10—N1	−0.5 (2)	C18—C19—C20—C15	1.2 (4)
C6—C5—C10—C9	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F91Aⁱ	0.93	2.50	3.336 (2)	150
C14—H14C···F91Cⁱⁱ	0.96	2.55	3.384 (2)	146
C17—H17···F91Cⁱⁱⁱ	0.93	2.54	3.425 (3)	160

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆F₃N₃
M_r	343.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.2811 (9), 14.8443 (15), 13.5325 (15)
β (°)	90.601 (9)
V (Å³)	1663.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.4 × 0.15 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 large Be window diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.737, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8893, 3391, 2248
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.156, 1.12
No. of reflections	3391
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F91Aⁱ	0.93	2.50	3.336 (2)	150
C14—H14C···F91Cⁱⁱ	0.96	2.55	3.384 (2)	146
C17—H17···F91Cⁱⁱⁱ	0.93	2.54	3.425 (3)	160

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

Acknowledgements

ANM thanks the University of Mysore for research facilities

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Domenicano, A. (1988). Stereochemical Applications of Gas-Phase Electron Diffraction, edited by I. Hargittai & M. Hargittai, pp. 281–324. New York: VCH. Google Scholar
Jasinski, J. P., Butcher, R. J., Narayana, B., Sunil, K. & Yathirajan, H. S. (2008). Acta Cryst. E64, o481–o482. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, UK. Google Scholar
Serbutoviez, C., Bosshard, C., Knöpfle, G., Wyss, P., Prêtre, P., Günter, P., Schenk, K., Solari, E. & Chapuis, G. (1995). Chem. Mater. 7, 1198–1206. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1989). Stereochemical Workstation Operation Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Sunil, K. & Bolte, M. (2007). Acta Cryst. E63, o2720–o2721. Web of Science CSD CrossRef IUCr Journals Google Scholar