(E)-1-(4-Methyl-phen-yl)ethanone [8-(trifluoro-meth-yl)quinolin-4-yl]hydrazone.

In the title compound, C(19)H(16)F(3)N(3), 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 inter-actions join the mol-ecules 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 ▶).

Experimental

Crystal data

C19H16F3N3

M = 343.35

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.156

S = 1.12

3391 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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.

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

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

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

C19H16F3N3	F(000) = 712
Mr = 343.35	Dx = 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

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	Rint = 0.021
Detector resolution: 8.1929 pixels mm-1	θmax = 28.1°, θmin = 3.0°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −17→19
Tmin = 0.737, Tmax = 1.000	l = −17→13
8893 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.0897P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
3391 reflections	Δρmax = 0.25 e Å−3
229 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .