3,4-Dimeth­oxy­benzaldehyde [2,8-bis­(trifluoro­meth­yl)quinolin-4-yl]hydrazone

Al-eryani, W.F.A.; Kumari, J.S.; Arunkashi, H.K.; Vepuri, S.B.; Devarajegowda, H.C.

doi:10.1107/S1600536810021616

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1742

doi:10.1107/S1600536810021616

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3,4-Dimethoxybenzaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone

Waleed Fedl Ali Al-eryani,^a J. Shylaja Kumari,^b H. K. Arunkashi,^a Suresh Babu Vepuri ^c and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India, and ^cDepartment of Pharmaceutical Chemistry, GITAM Institute of Pharmacy, GITAM University, Visakhapatnam 530 045, Andhrapradesh, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 29 May 2010; accepted 7 June 2010; online 23 June 2010)

In the title compound, C₂₀H₁₅F₆N₃O₂, 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 intermolecular C—H⋯F hydrogen bond. In addition, a weak π–π interaction 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_r = 443.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.175
S = 1.03
3756 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) x, y+1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

2,8-Bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol (mefloquin) is a popular antimalarial drug. Further, studies have reported that it also possesses important structural features required for antimicrobial activity (Mao et al. 2009; Bermudez et al. 2004; Jayaprakash et al. 2006). Quinoline is the essential structural feature found in mefloquin and recently developed antimycobacterial drugs (Andries et al. 2005). Thus, quinoline derivatives are good lead molecules to further develop drug candidates against mycobacterium tuberculosis and as antibacterial agents. On the basis of these observations we have synthesized a quinoline derivative, in which a hydrazone group has been attached at the 4 position of the mefloquin structure, expecting that the newly designed molecule would exhibit some antibacterial activity. In this paper we report the crystal structure of 3,4-dimethoxybenzaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone.

The asymmetric unit of the title compound contains one molecule (Fig. 1). A very small dihedral angle [2.31 (8)°] between the quinoline system and the benzene ring indicates that these two systems are coplanar. In the crystal structure, intermolecular C12—H12···F1 hydrogen bonding (Table 1) involving the trifluoromethyl and methine groups results in the formation of a three-dimensional ladder-type network (Fig.2). In addition, a weak π-π interaction is observed between the benzene ring (C1-C6) and benzene ring (C13-C18) of quinoline, with a centroid-centroid distance of 3.586 (1) Å.

The crystal structures of the mefloquine base and its salt complexes have been reported (Skörska et al. 2005). However, these are only related to the quinoline portion of our structure.

Related literature top

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 top

A mixture of [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazine (10 mmol) and 3,4 trimethoxy benzaldehyde (10 mmol) in glacial acetic acid (50 ml) was heated at reflux for 3 h. The reaction mixture was concentrated under reduced pressure, cooled, and the resulting solid hydrazone was filtered, washed with water and cold ethanol. The crude product was purified by column chromatography. Crystals suitable for X-ray analysis were obtained by dissolving the pure compound in hot methanol and slow evaporation of the solvent at room temperature. Yield: 72%, Mp. 487 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Packing of the molecules showing hydrogen bonds as dashed lines.

3,4-Dimethoxybenzaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone top

Crystal data top

C₂₀H₁₅F₆N₃O₂	Z = 2
M_r = 443.35	F(000) = 452
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.0861P)² + 0.4197P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3756 reflections	Δρ_max = 0.51 e Å⁻³
281 parameters	Δρ_min = −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)

Crystal data top

C₂₀H₁₅F₆N₃O₂	γ = 96.449 (1)°
M_r = 443.35	V = 970.75 (15) Å³
Triclinic, P1	Z = 2
a = 7.0359 (6) Å	Mo Kα radiation
b = 8.9617 (8) Å	µ = 0.14 mm⁻¹
c = 15.5315 (14) Å	T = 298 K
α = 90.154 (1)°	0.22 × 0.15 × 0.12 mm
β = 93.951 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3756 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	2951 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.984	R_int = 0.023
9677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.03	Δρ_max = 0.51 e Å⁻³
3756 reflections	Δρ_min = −0.31 e Å⁻³
281 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅F₆N₃O₂
M_r	443.35
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0359 (6), 8.9617 (8), 15.5315 (14)
α, β, γ (°)	90.154 (1), 93.951 (1), 96.449 (1)
V (Å³)	970.75 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	ψ scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.975, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9677, 3756, 2951
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.175, 1.03
No. of reflections	3756
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Acknowledgements

We thank the DST, India, for funding under DST-FIST (Level II) for the X-ray diffraction facility at SSCU, IISc, Bangalore.

References

Andries, K., Verhasselt, P., Guillemont, J., Gohlmann, H. W., Neefs, J. M., Winkler, H., Van Gestel, J., Timmerman, P., Zhu, M., Lee, E., Williams, P., de Chaffoy, D., Huitric, E., Hoffner, S., Cambau, E., Truffot-Pernot, C., Lounis, N. & Jarlier, V. (2005). Science, 307, 223–227. Web of Science CrossRef PubMed CAS Google Scholar
Bermudez, L. E., Kolonoski, P., Seitz, L. E., Petrofsky, M., Reynolds, R., Wu, M. & Young, L. S. (2004). Antimicrob. Agents Chemother. 48, 3556–3558. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jayaprakash, S., Iso, Y., Wan, B., Franzblau, S. G. & Kozikowski, A. P. (2006). ChemMedChem, 1, 593–597. Web of Science CrossRef PubMed CAS Google Scholar
Mao, J., Yuan, H., Wang, Y., Wan, B., Pieroni, M., Huang, Q., Breemen, R. B., Kozikowski, A. P. & Franzblau, S. G. (2009). J. Med. Chem. 52, 6966–6978. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skörska, A., Sliwinski, J. & Oleksyn, B. J. (2005). Bioorg. Med. Chem. Lett. 16, 850–853. Web of Science PubMed Google Scholar

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Volume 66| Part 7| July 2010| Page o1742

doi:10.1107/S1600536810021616

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,4-Dimeth­­oxy­benzaldehyde [2,8-bis­­(tri­fluoro­meth­yl)quinolin-4-yl]hydrazone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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3,4-Dimethoxybenzaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone