3,4-Dimeth-oxy-benzaldehyde [2,8-bis-(trifluoro-meth-yl)quinolin-4-yl]hydrazone.

In the title compound, C(20)H(15)F(6)N(3)O(2), the quinoline ring system is almost coplanar with the benzene ring; the dihedral angle between the two planes is 2.31 (8)°. The crystal structure displays an inter-molecular C-H⋯F hydrogen bond. In addition, a weak π-π inter-action is observed between the unfused benzene ring and the benzene ring of quinoline, with a centroid-centroid distance of 3.586 (1) Å.

Related literature

For general background to quinolines, see: Mao et al. (2009 ▶); Bermudez et al.(2004 ▶); Jayaprakash et al. (2006 ▶); Andries et al. (2005 ▶). For related structures, see: Skörska et al. (2005 ▶).

Experimental

Crystal data

C20H15F6N3O2

M = 443.35

Triclinic,

a = 7.0359 (6) Å

b = 8.9617 (8) Å

c = 15.5315 (14) Å

α = 90.154 (1)°

β = 93.951 (1)°

γ = 96.449 (1)°

V = 970.75 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ▶) T min = 0.975, T max = 0.984

9677 measured reflections

3756 independent reflections

2951 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.175

S = 1.03

3756 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021616/wn2391sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021616/wn2391Isup2.hkl

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

C20H15F6N3O2	Z = 2
Mr = 443.35	F(000) = 452
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Melting point: 487 K
a = 7.0359 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9617 (8) Å	Cell parameters from 3756 reflections
c = 15.5315 (14) Å	θ = 2.3–25.9°
α = 90.154 (1)°	µ = 0.14 mm−1
β = 93.951 (1)°	T = 298 K
γ = 96.449 (1)°	Plate, colourless
V = 970.75 (15) Å3	0.22 × 0.15 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	2951 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 25.9°, θmin = 2.3°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −8→8
Tmin = 0.975, Tmax = 0.984	k = −11→11
9677 measured reflections	l = −19→19

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.0861P)2 + 0.4197P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3756 reflections	Δρmax = 0.51 e Å−3
281 parameters	Δρmin = −0.31 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: 0.013 (3)

Experimental. 1H NMR (300 MHz, CD3 OD): δ, 3.886 (s, 3H, OCH3), 3.930 (s, 3H, OCH3) 7.047-7.019 (d, IH, 3,4-dimethoxyphenyl, J = 8.1Hz) 7.297-7.269 (t, 1H, trifluoromethylquinoline, J = 8.4Hz), 7.46 (s, IH, trifluoromethylquinoline), 7.667-7.640 (d, 1H, 3,4-dimethoxyphenyl, J=8.1Hz), 8.138-8.114 (d, 1H, trifluoromethylquinoline, J=7.2Hz), 8.26 (s, 1H, =CH), 8.263 (s, IH, 3,4-dimethoxyphenyl), 8.527-8.498 (d, IH, trifluoromethylquinoline, J=8.7Hz), 8.52 (s, 1H, N-H).

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
F1	0.2412 (5)	0.4438 (2)	1.01640 (13)	0.1566 (13)
F2	0.1191 (7)	0.3559 (3)	1.1239 (2)	0.211 (2)
F3	0.4056 (6)	0.3784 (3)	1.1201 (2)	0.1887 (16)
F4	0.1562 (3)	0.5209 (2)	1.39246 (11)	0.0901 (5)
F5	0.3417 (3)	0.6419 (2)	1.48883 (9)	0.0978 (6)
F6	0.4605 (3)	0.5329 (2)	1.38655 (10)	0.0913 (6)
O1	0.1621 (3)	1.07781 (19)	0.57898 (9)	0.0638 (5)
O2	0.1874 (3)	0.83177 (18)	0.65840 (10)	0.0688 (5)
N1	0.2843 (3)	0.6043 (2)	1.22381 (12)	0.0578 (5)
N2	0.2663 (3)	0.98738 (19)	1.07163 (10)	0.0507 (5)
H2	0.2733	1.0750	1.0951	0.061*
N3	0.2477 (3)	0.97088 (19)	0.98344 (10)	0.0482 (4)
C1	0.3304 (3)	1.0213 (3)	1.34583 (14)	0.0580 (6)
H1	0.3429	1.1138	1.3742	0.070*
C2	0.3326 (3)	0.8892 (3)	1.39354 (14)	0.0582 (6)
H2A	0.3449	0.8943	1.4535	0.070*
C3	0.3169 (3)	0.7533 (3)	1.35271 (13)	0.0525 (5)
C4	0.2979 (3)	0.7427 (2)	1.26103 (13)	0.0470 (5)
C5	0.2936 (3)	0.8770 (2)	1.21338 (12)	0.0436 (5)
C6	0.3100 (3)	1.0148 (2)	1.25823 (13)	0.0518 (5)
H6	0.3069	1.1034	1.2273	0.062*
C7	0.3190 (4)	0.6124 (3)	1.40417 (15)	0.0689 (7)
C8	0.2689 (4)	0.6011 (2)	1.13901 (14)	0.0591 (6)
C9	0.2625 (3)	0.7229 (2)	1.08485 (13)	0.0538 (5)
H9	0.2509	0.7099	1.0252	0.065*
C10	0.2736 (3)	0.8634 (2)	1.12140 (12)	0.0444 (5)
C11	0.2571 (6)	0.4467 (3)	1.09982 (19)	0.0922 (11)
C12	0.2377 (3)	1.0891 (2)	0.94007 (13)	0.0506 (5)
H12	0.2427	1.1804	0.9692	0.061*
C13	0.2186 (3)	1.0878 (2)	0.84631 (12)	0.0450 (5)
C14	0.2105 (3)	0.9538 (2)	0.79899 (13)	0.0478 (5)
H14	0.2167	0.8636	0.8279	0.057*
C15	0.1934 (3)	0.9543 (2)	0.71040 (13)	0.0492 (5)
C16	0.1818 (3)	1.0908 (2)	0.66624 (12)	0.0478 (5)
C17	0.1917 (3)	1.2227 (2)	0.71299 (13)	0.0521 (5)
H17	0.1863	1.3134	0.6845	0.063*
C18	0.2096 (3)	1.2204 (2)	0.80233 (13)	0.0514 (5)
H18	0.2156	1.3101	0.8332	0.062*
C19	0.2110 (5)	0.6924 (3)	0.69794 (18)	0.0804 (8)
H19A	0.2042	0.6154	0.6544	0.121*
H19B	0.1113	0.6681	0.7365	0.121*
H19C	0.3335	0.6989	0.7298	0.121*
C20	0.1384 (4)	1.2097 (3)	0.53018 (14)	0.0654 (7)
H20A	0.1262	1.1847	0.4698	0.098*
H20B	0.2480	1.2825	0.5421	0.098*
H20C	0.0251	1.2506	0.5458	0.098*

	U11	U22	U33	U12	U13	U23
F1	0.342 (4)	0.0590 (11)	0.0692 (12)	0.0322 (16)	0.0014 (16)	−0.0190 (9)
F2	0.345 (5)	0.0832 (16)	0.196 (3)	−0.085 (2)	0.128 (3)	−0.0574 (17)
F3	0.282 (4)	0.1017 (18)	0.190 (3)	0.103 (2)	−0.062 (3)	−0.0563 (18)
F4	0.0978 (12)	0.0869 (12)	0.0843 (11)	0.0028 (9)	0.0072 (9)	0.0326 (9)
F5	0.1344 (16)	0.1228 (15)	0.0411 (8)	0.0407 (12)	−0.0016 (8)	0.0207 (8)
F6	0.1058 (13)	0.1033 (13)	0.0741 (10)	0.0536 (10)	0.0027 (9)	0.0238 (9)
O1	0.0832 (11)	0.0717 (11)	0.0365 (8)	0.0125 (8)	−0.0023 (7)	0.0003 (7)
O2	0.1029 (13)	0.0560 (9)	0.0466 (9)	0.0126 (9)	−0.0081 (8)	−0.0122 (7)
N1	0.0775 (13)	0.0495 (10)	0.0471 (10)	0.0120 (9)	0.0014 (9)	0.0041 (8)
N2	0.0750 (12)	0.0433 (9)	0.0338 (9)	0.0082 (8)	0.0023 (8)	−0.0030 (7)
N3	0.0617 (11)	0.0477 (9)	0.0352 (9)	0.0071 (8)	0.0016 (7)	−0.0013 (7)
C1	0.0635 (14)	0.0646 (14)	0.0457 (12)	0.0051 (11)	0.0053 (10)	−0.0152 (10)
C2	0.0559 (13)	0.0826 (16)	0.0356 (10)	0.0082 (11)	−0.0001 (9)	−0.0064 (10)
C3	0.0480 (11)	0.0712 (14)	0.0388 (11)	0.0114 (10)	−0.0001 (8)	0.0043 (10)
C4	0.0475 (11)	0.0536 (12)	0.0403 (10)	0.0092 (9)	−0.0003 (8)	0.0019 (8)
C5	0.0433 (10)	0.0494 (11)	0.0381 (10)	0.0061 (8)	0.0015 (8)	−0.0027 (8)
C6	0.0580 (12)	0.0523 (12)	0.0450 (11)	0.0053 (9)	0.0053 (9)	−0.0043 (9)
C7	0.0754 (17)	0.0861 (18)	0.0475 (13)	0.0230 (15)	−0.0017 (11)	0.0141 (12)
C8	0.0836 (16)	0.0457 (12)	0.0479 (12)	0.0085 (11)	0.0013 (11)	−0.0017 (9)
C9	0.0763 (15)	0.0484 (12)	0.0363 (10)	0.0077 (10)	−0.0004 (9)	−0.0035 (8)
C10	0.0492 (11)	0.0457 (11)	0.0382 (10)	0.0059 (8)	0.0003 (8)	0.0009 (8)
C11	0.172 (4)	0.0439 (14)	0.0622 (17)	0.0193 (18)	0.0067 (18)	0.0032 (12)
C12	0.0666 (13)	0.0453 (11)	0.0404 (11)	0.0091 (9)	0.0034 (9)	−0.0034 (9)
C13	0.0497 (11)	0.0479 (11)	0.0376 (10)	0.0065 (8)	0.0027 (8)	−0.0005 (8)
C14	0.0542 (12)	0.0468 (11)	0.0419 (11)	0.0063 (9)	−0.0002 (9)	0.0019 (8)
C15	0.0518 (11)	0.0524 (12)	0.0426 (11)	0.0054 (9)	−0.0032 (9)	−0.0067 (9)
C16	0.0485 (11)	0.0588 (12)	0.0361 (10)	0.0078 (9)	0.0006 (8)	−0.0006 (9)
C17	0.0624 (13)	0.0510 (12)	0.0438 (11)	0.0101 (10)	0.0037 (9)	0.0079 (9)
C18	0.0664 (13)	0.0465 (11)	0.0422 (11)	0.0096 (9)	0.0049 (9)	−0.0031 (9)
C19	0.125 (3)	0.0507 (14)	0.0645 (16)	0.0107 (14)	0.0008 (15)	−0.0115 (11)
C20	0.0732 (15)	0.0844 (17)	0.0398 (11)	0.0141 (13)	0.0027 (10)	0.0113 (11)

F1—C11	1.293 (3)	C5—C6	1.406 (3)
F2—C11	1.272 (5)	C5—C10	1.429 (3)
F3—C11	1.291 (5)	C6—H6	0.9300
F4—C7	1.333 (3)	C8—C9	1.383 (3)
F5—C7	1.336 (3)	C8—C11	1.502 (3)
F6—C7	1.330 (3)	C9—C10	1.372 (3)
O1—C16	1.356 (2)	C9—H9	0.9300
O1—C20	1.425 (3)	C12—C13	1.453 (3)
O2—C15	1.357 (3)	C12—H12	0.9300
O2—C19	1.415 (3)	C13—C18	1.378 (3)
N1—C8	1.314 (3)	C13—C14	1.399 (3)
N1—C4	1.358 (3)	C14—C15	1.373 (3)
N2—C10	1.359 (3)	C14—H14	0.9300
N2—N3	1.373 (2)	C15—C16	1.412 (3)
N2—H2	0.8600	C16—C17	1.378 (3)
N3—C12	1.263 (3)	C17—C18	1.385 (3)
C1—C6	1.359 (3)	C17—H17	0.9300
C1—C2	1.399 (3)	C18—H18	0.9300
C1—H1	0.9300	C19—H19A	0.9600
C2—C3	1.362 (3)	C19—H19B	0.9600
C2—H2A	0.9300	C19—H19C	0.9600
C3—C4	1.423 (3)	C20—H20A	0.9600
C3—C7	1.497 (3)	C20—H20B	0.9600
C4—C5	1.417 (3)	C20—H20C	0.9600
C16—O1—C20	118.09 (18)	F2—C11—F3	103.2 (3)
C15—O2—C19	117.76 (18)	F2—C11—F1	106.1 (3)
C8—N1—C4	115.71 (18)	F3—C11—F1	104.6 (3)
C10—N2—N3	119.15 (16)	F2—C11—C8	114.2 (3)
C10—N2—H2	120.4	F3—C11—C8	113.4 (3)
N3—N2—H2	120.4	F1—C11—C8	114.3 (2)
C12—N3—N2	116.75 (17)	N3—C12—C13	122.43 (19)
C6—C1—C2	120.2 (2)	N3—C12—H12	118.8
C6—C1—H1	119.9	C13—C12—H12	118.8
C2—C1—H1	119.9	C18—C13—C14	118.76 (18)
C3—C2—C1	120.41 (19)	C18—C13—C12	119.92 (18)
C3—C2—H2A	119.8	C14—C13—C12	121.32 (18)
C1—C2—H2A	119.8	C15—C14—C13	120.70 (19)
C2—C3—C4	120.8 (2)	C15—C14—H14	119.7
C2—C3—C7	120.1 (2)	C13—C14—H14	119.7
C4—C3—C7	119.0 (2)	O2—C15—C14	125.5 (2)
N1—C4—C5	123.44 (18)	O2—C15—C16	114.57 (18)
N1—C4—C3	118.27 (19)	C14—C15—C16	119.92 (19)
C5—C4—C3	118.29 (19)	O1—C16—C17	125.84 (19)
C6—C5—C4	118.94 (18)	O1—C16—C15	114.91 (18)
C6—C5—C10	123.79 (19)	C17—C16—C15	119.25 (18)
C4—C5—C10	117.27 (18)	C16—C17—C18	120.15 (19)
C1—C6—C5	121.3 (2)	C16—C17—H17	119.9
C1—C6—H6	119.3	C18—C17—H17	119.9
C5—C6—H6	119.3	C13—C18—C17	121.22 (19)
F6—C7—F4	107.0 (2)	C13—C18—H18	119.4
F6—C7—F5	106.04 (19)	C17—C18—H18	119.4
F4—C7—F5	105.7 (2)	O2—C19—H19A	109.5
F6—C7—C3	113.2 (2)	O2—C19—H19B	109.5
F4—C7—C3	112.9 (2)	H19A—C19—H19B	109.5
F5—C7—C3	111.5 (2)	O2—C19—H19C	109.5
N1—C8—C9	126.8 (2)	H19A—C19—H19C	109.5
N1—C8—C11	114.4 (2)	H19B—C19—H19C	109.5
C9—C8—C11	118.8 (2)	O1—C20—H20A	109.5
C10—C9—C8	118.24 (19)	O1—C20—H20B	109.5
C10—C9—H9	120.9	H20A—C20—H20B	109.5
C8—C9—H9	120.9	O1—C20—H20C	109.5
N2—C10—C9	121.02 (18)	H20A—C20—H20C	109.5
N2—C10—C5	120.47 (18)	H20B—C20—H20C	109.5
C9—C10—C5	118.52 (18)
C10—N2—N3—C12	178.62 (19)	C6—C5—C10—N2	−1.1 (3)
C6—C1—C2—C3	0.9 (3)	C4—C5—C10—N2	179.28 (18)
C1—C2—C3—C4	0.0 (3)	C6—C5—C10—C9	178.8 (2)
C1—C2—C3—C7	−179.9 (2)	C4—C5—C10—C9	−0.8 (3)
C8—N1—C4—C5	0.8 (3)	N1—C8—C11—F2	57.4 (5)
C8—N1—C4—C3	−179.4 (2)	C9—C8—C11—F2	−122.5 (4)
C2—C3—C4—N1	179.5 (2)	N1—C8—C11—F3	−60.4 (4)
C7—C3—C4—N1	−0.7 (3)	C9—C8—C11—F3	119.7 (3)
C2—C3—C4—C5	−0.7 (3)	N1—C8—C11—F1	179.8 (3)
C7—C3—C4—C5	179.15 (19)	C9—C8—C11—F1	−0.1 (5)
N1—C4—C5—C6	−179.6 (2)	N2—N3—C12—C13	179.74 (19)
C3—C4—C5—C6	0.6 (3)	N3—C12—C13—C18	−179.6 (2)
N1—C4—C5—C10	0.1 (3)	N3—C12—C13—C14	−0.1 (3)
C3—C4—C5—C10	−179.77 (18)	C18—C13—C14—C15	−0.2 (3)
C2—C1—C6—C5	−0.9 (3)	C12—C13—C14—C15	−179.7 (2)
C4—C5—C6—C1	0.2 (3)	C19—O2—C15—C14	−3.6 (4)
C10—C5—C6—C1	−179.4 (2)	C19—O2—C15—C16	175.9 (2)
C2—C3—C7—F6	−120.9 (2)	C13—C14—C15—O2	178.9 (2)
C4—C3—C7—F6	59.2 (3)	C13—C14—C15—C16	−0.6 (3)
C2—C3—C7—F4	117.4 (3)	C20—O1—C16—C17	−3.8 (3)
C4—C3—C7—F4	−62.4 (3)	C20—O1—C16—C15	176.45 (19)
C2—C3—C7—F5	−1.5 (3)	O2—C15—C16—O1	1.5 (3)
C4—C3—C7—F5	178.7 (2)	C14—C15—C16—O1	−178.97 (19)
C4—N1—C8—C9	−1.0 (4)	O2—C15—C16—C17	−178.3 (2)
C4—N1—C8—C11	179.1 (3)	C14—C15—C16—C17	1.2 (3)
N1—C8—C9—C10	0.2 (4)	O1—C16—C17—C18	179.2 (2)
C11—C8—C9—C10	−179.9 (3)	C15—C16—C17—C18	−1.0 (3)
N3—N2—C10—C9	−0.1 (3)	C14—C13—C18—C17	0.4 (3)
N3—N2—C10—C5	179.80 (17)	C12—C13—C18—C17	179.9 (2)
C8—C9—C10—N2	−179.4 (2)	C16—C17—C18—C13	0.2 (3)
C8—C9—C10—C5	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1i	0.93	2.47	3.387 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1i	0.93	2.47	3.387 (3)	168

Symmetry code: (i) .