Nicotinaldehyde [2,8-bis­(trifluoro­meth­yl)quinolin-4-yl]hydrazone monohydrate

Devarajegowda, H.C.; Vepuri, S.B.; VinduVahini, M.; Kavitha, H.D.; Arunkashi, H.K.

doi:10.1107/S1600536810030862

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2237-o2238

https://doi.org/10.1107/S1600536810030862

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Nicotinaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone monohydrate

H. C. Devarajegowda,^a ^* Suresh Babu Vepuri,^b M. VinduVahini,^c H. D. Kavitha ^d and H. K. Arunkashi ^a

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, ^bDepartment of Pharmaceutical Chemistry, GITAM Institute of Pharmacy, GITAM University, Visakhapatnam 530045, Andhrapradesh, India, ^cDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India, and ^dDepartment of Physics, Govt. Science College, Hassan 573 201, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 29 June 2010; accepted 2 August 2010; online 11 August 2010)

In the title compound, C₁₇H₁₀F₆N₄·H₂O, the pyridine ring is not coplanar with the quinoline ring system; the dihedral angle between the two planes is 21.3 (1)°. One of the trifluoromethyl group is disordered over two orientations with occupancies of 0.70 (1) and 0.30 (1). The water molecule is disordered over two positions with occupancies of 0.76 (1) and 0.24 (1). In the crystal, the water molecule is linked to the main molecule via N—H⋯O and C—H⋯O hydrogen bonds, and inversion-related pairs are linked via O—H⋯N hydrogen bonds. In addition, a weak π–π interaction is observed between the pyridine ring and the pyridine ring of the quinoline unit, with a centroid–centroid distance of 3.650 (2) 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: Al-eryani et al. (2010 ); Skörska et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₀F₆N₄·H₂O
M_r = 402.31
Monoclinic, C 2/c
a = 21.103 (4) Å
b = 15.120 (3) Å
c = 12.537 (3) Å
β = 118.633 (3)°
V = 3511.1 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 295 K
0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Bruker, 2001 ) T_min = 0.975, T_max = 0.983
13267 measured reflections
3416 independent reflections
2309 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.169
S = 1.04
3416 reflections
301 parameters
54 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1W	0.88 (3)	2.04 (3)	2.914 (5)	169 (3)
O1W—H1W⋯N4ⁱ	0.83 (5)	2.06 (6)	2.855 (5)	163 (7)
C9—H9⋯O1W	0.93	2.42	3.331 (5)	167
Symmetry code: (i) -x+1, -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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810030862/ci5125sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030862/ci5125Isup2.hkl

checkCIF report

Comment top

2,8-Bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol (mefloquin) is a popular antimalarial drug. It also possesses important structural features required for antimicrobial activity (Mao et al. 2009; Bermudez et al. 2004; Jayaprakash et al. 2006). Quinoline is an essential structural unit 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 few quinoline derivatives, in which a hydrazone group has been attached at the 4th position of the mefloquin ring system, expecting that these newly designed molecules would exhibit some antibacterial activity. The crystal structures of the mefloquine base and its salt complexes have been reported (Skörska et al. 2005). Earlier, we reported the crystal structure of 3,4-dimethoxybenzaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone (Al-eryani et al., 2010). We report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains one nicotinaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone molecule and one water molecule (Fig. 1). The dihedral angle [21.3 (1)°] between the quinoline ring system and the pyridine ring indicates that these two systems are non coplanar.

In the crystal structure, intermolecular O—H···N, N—H···O and C—H···O hydrogen bonds (Table 1) are observed. In addition, a weak π–π interaction is observed between N4/C13–C17 pyridine ring at (-x, y, 1/2-z) and N1/C1–C5 pyridine ring of quinoline at (x,y,z), with a centroid-centroid distance of 3.650 (3) Å.

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: Al-eryani et al. (2010); Skörska et al. (2005).

Experimental top

A mixture of [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazine (10 mmol) and nicotinaldehyde (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 obtained solid hydrazone was filtered, washed with water and cold ethanol. The crude product was purified by column chromatography. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an methanol-water solution at room temperature.

Structure description 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: Al-eryani et al. (2010); Skörska et al. (2005).

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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Only the major disorder components are shown. Dashed lines indicate hydrogen bonds.

Nicotinaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone monohydrate top

Crystal data top

C₁₇H₁₀F₆N₄·H₂O	F(000) = 1632
M_r = 402.31	D_x = 1.522 Mg m⁻³
Monoclinic, C2/c	Melting point: 486 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.103 (4) Å	Cell parameters from 3416 reflections
b = 15.120 (3) Å	θ = 1.7–26.0°
c = 12.537 (3) Å	µ = 0.14 mm⁻¹
β = 118.633 (3)°	T = 295 K
V = 3511.1 (13) Å³	Plate, colourless
Z = 8	0.22 × 0.15 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2309 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: ψ scan (SADABS; Bruker, 2001)	h = −26→24
T_min = 0.975, T_max = 0.983	k = −18→18
13267 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0764P)² + 2.423P] where P = (F_o² + 2F_c²)/3
3416 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 0.26 e Å⁻³
54 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₇H₁₀F₆N₄·H₂O	V = 3511.1 (13) Å³
M_r = 402.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.103 (4) Å	µ = 0.14 mm⁻¹
b = 15.120 (3) Å	T = 295 K
c = 12.537 (3) Å	0.22 × 0.15 × 0.12 mm
β = 118.633 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3416 independent reflections
Absorption correction: ψ scan (SADABS; Bruker, 2001)	2309 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.035
13267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	54 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.26 e Å⁻³
3416 reflections	Δρ_min = −0.25 e Å⁻³
301 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 > 2sigma(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	Occ. (<1)
F1A	0.5904 (2)	−0.0211 (2)	0.5513 (4)	0.0998 (17)	0.702 (8)
F2A	0.6589 (4)	−0.0445 (5)	0.4831 (7)	0.136 (3)	0.702 (8)
F3A	0.5538 (5)	−0.0032 (4)	0.3634 (5)	0.175 (4)	0.702 (8)
F1B	0.6012 (6)	−0.0127 (6)	0.3579 (8)	0.091 (3)	0.298 (8)
F2B	0.5395 (6)	0.0067 (8)	0.4374 (17)	0.130 (5)	0.298 (8)
F3B	0.6570 (7)	−0.0477 (7)	0.5238 (10)	0.110 (6)	0.298 (8)
F4	0.80847 (12)	0.08843 (14)	0.83893 (19)	0.0933 (7)
F5	0.71855 (14)	0.12394 (18)	0.8610 (2)	0.1087 (8)
F6	0.81994 (15)	0.18889 (16)	0.96395 (17)	0.1198 (10)
N1	0.68113 (12)	0.11985 (15)	0.6073 (2)	0.0554 (6)
N2	0.61107 (14)	0.31173 (19)	0.3332 (2)	0.0623 (7)
N3	0.56960 (13)	0.28345 (17)	0.2162 (2)	0.0607 (7)
N4	0.42311 (17)	0.3601 (2)	−0.1996 (3)	0.0905 (10)
C1	0.63497 (15)	0.10370 (18)	0.4929 (2)	0.0558 (7)
C2	0.60955 (15)	0.16393 (18)	0.3984 (2)	0.0550 (7)
H2	0.5766	0.1468	0.3198	0.066*
C3	0.63410 (14)	0.24976 (18)	0.4233 (2)	0.0509 (7)
C4	0.68355 (14)	0.27268 (18)	0.5461 (2)	0.0505 (7)
C5	0.70505 (14)	0.20455 (17)	0.6345 (2)	0.0499 (7)
C6	0.75344 (16)	0.22617 (19)	0.7576 (2)	0.0581 (8)
C7	0.77952 (18)	0.3094 (2)	0.7890 (3)	0.0692 (9)
H7	0.8118	0.3222	0.8698	0.083*
C8	0.75865 (18)	0.3761 (2)	0.7019 (3)	0.0729 (9)
H8	0.7769	0.4330	0.7248	0.087*
C9	0.71174 (17)	0.35831 (19)	0.5837 (3)	0.0641 (8)
H9	0.6980	0.4035	0.5265	0.077*
C10	0.6071 (2)	0.0102 (2)	0.4681 (3)	0.0809 (11)
C11	0.7746 (2)	0.1574 (2)	0.8540 (3)	0.0750 (10)
C12	0.54235 (17)	0.3419 (2)	0.1340 (3)	0.0699 (9)
H12	0.5489	0.4015	0.1546	0.084*
C13	0.50072 (17)	0.3156 (2)	0.0070 (3)	0.0639 (8)
C14	0.49612 (17)	0.2291 (2)	−0.0322 (3)	0.0662 (9)
H14	0.5209	0.1843	0.0232	0.079*
C15	0.45503 (19)	0.2098 (2)	−0.1525 (3)	0.0755 (10)
H15	0.4508	0.1519	−0.1798	0.091*
C16	0.4200 (2)	0.2770 (3)	−0.2323 (3)	0.0813 (11)
H16	0.3926	0.2631	−0.3142	0.098*
C17	0.4624 (2)	0.3780 (2)	−0.0816 (3)	0.0893 (12)
H17	0.4642	0.4364	−0.0570	0.107*
O1W	0.6581 (3)	0.4946 (2)	0.3473 (4)	0.088 (2)	0.758 (13)
H1W	0.631 (3)	0.537 (3)	0.315 (6)	0.132*	0.758 (13)
H2W	0.695 (2)	0.498 (4)	0.341 (7)	0.132*	0.758 (13)
O2W	0.6032 (15)	0.5042 (8)	0.3654 (12)	0.119 (10)	0.242 (13)
H2N	0.6237 (16)	0.368 (2)	0.345 (3)	0.065 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.121 (3)	0.070 (2)	0.112 (3)	−0.0409 (19)	0.059 (3)	−0.0055 (18)
F2A	0.200 (6)	0.079 (4)	0.169 (7)	0.015 (3)	0.120 (5)	−0.009 (4)
F3A	0.186 (6)	0.087 (3)	0.093 (3)	−0.068 (4)	−0.062 (3)	0.022 (3)
F1B	0.098 (6)	0.065 (4)	0.089 (6)	−0.019 (5)	0.027 (5)	−0.040 (4)
F2B	0.117 (8)	0.105 (7)	0.198 (12)	−0.053 (5)	0.099 (8)	−0.042 (7)
F3B	0.150 (9)	0.039 (4)	0.060 (5)	−0.002 (5)	−0.014 (5)	0.019 (4)
F4	0.0962 (15)	0.0700 (13)	0.0804 (14)	0.0121 (11)	0.0155 (12)	0.0131 (10)
F5	0.1159 (19)	0.126 (2)	0.0824 (15)	−0.0115 (15)	0.0462 (14)	0.0322 (13)
F6	0.156 (2)	0.0963 (16)	0.0446 (11)	−0.0156 (14)	−0.0024 (12)	0.0008 (10)
N1	0.0587 (14)	0.0482 (13)	0.0457 (13)	−0.0017 (11)	0.0141 (11)	0.0017 (10)
N2	0.0664 (17)	0.0551 (16)	0.0467 (13)	−0.0082 (12)	0.0122 (12)	0.0045 (11)
N3	0.0571 (15)	0.0648 (15)	0.0470 (13)	−0.0053 (12)	0.0144 (12)	0.0066 (11)
N4	0.098 (2)	0.087 (2)	0.0532 (16)	−0.0108 (17)	0.0094 (16)	0.0226 (16)
C1	0.0562 (17)	0.0488 (16)	0.0488 (15)	0.0003 (13)	0.0142 (13)	−0.0010 (12)
C2	0.0518 (16)	0.0546 (17)	0.0428 (14)	−0.0016 (13)	0.0099 (12)	−0.0031 (12)
C3	0.0465 (15)	0.0529 (16)	0.0458 (15)	0.0019 (12)	0.0162 (12)	0.0028 (12)
C4	0.0456 (15)	0.0509 (16)	0.0490 (15)	−0.0003 (12)	0.0178 (13)	−0.0010 (12)
C5	0.0463 (15)	0.0503 (16)	0.0455 (14)	0.0014 (12)	0.0158 (12)	0.0003 (12)
C6	0.0588 (18)	0.0577 (17)	0.0464 (15)	−0.0016 (14)	0.0160 (13)	−0.0028 (13)
C7	0.071 (2)	0.065 (2)	0.0496 (16)	−0.0067 (16)	0.0111 (15)	−0.0099 (15)
C8	0.076 (2)	0.0534 (18)	0.064 (2)	−0.0126 (16)	0.0141 (17)	−0.0098 (15)
C9	0.0663 (19)	0.0486 (17)	0.0614 (18)	−0.0040 (14)	0.0177 (15)	0.0032 (13)
C10	0.093 (3)	0.053 (2)	0.063 (2)	0.0027 (19)	0.010 (2)	−0.0039 (17)
C11	0.086 (3)	0.068 (2)	0.0471 (18)	−0.0073 (19)	0.0134 (17)	0.0009 (15)
C12	0.071 (2)	0.0597 (19)	0.0548 (18)	−0.0084 (15)	0.0108 (16)	0.0102 (14)
C13	0.0595 (18)	0.066 (2)	0.0538 (17)	−0.0075 (14)	0.0174 (15)	0.0150 (14)
C14	0.065 (2)	0.069 (2)	0.0581 (18)	0.0049 (16)	0.0240 (16)	0.0125 (15)
C15	0.082 (2)	0.080 (2)	0.059 (2)	0.0000 (19)	0.0292 (18)	−0.0011 (17)
C16	0.080 (2)	0.100 (3)	0.0503 (18)	−0.007 (2)	0.0203 (17)	0.0073 (19)
C17	0.098 (3)	0.070 (2)	0.062 (2)	−0.014 (2)	0.0081 (19)	0.0199 (17)
O1W	0.102 (4)	0.064 (2)	0.081 (2)	−0.010 (2)	0.029 (2)	0.0169 (17)
O2W	0.18 (2)	0.062 (7)	0.093 (9)	0.001 (8)	0.047 (10)	0.014 (6)

Geometric parameters (Å, º) top

F1A—C10	1.337 (5)	C4—C9	1.408 (4)
F2A—C10	1.312 (6)	C4—C5	1.419 (4)
F3A—C10	1.269 (5)	C5—C6	1.422 (4)
F1B—C10	1.370 (7)	C6—C7	1.354 (4)
F2B—C10	1.288 (8)	C6—C11	1.491 (4)
F3B—C10	1.288 (8)	C7—C8	1.394 (5)
F4—C11	1.328 (4)	C7—H7	0.93
F5—C11	1.328 (4)	C8—C9	1.357 (4)
F6—C11	1.334 (4)	C8—H8	0.93
N1—C1	1.314 (3)	C9—H9	0.93
N1—C5	1.359 (3)	C12—C13	1.457 (4)
N2—C3	1.365 (4)	C12—H12	0.93
N2—N3	1.367 (3)	C13—C14	1.384 (5)
N2—H2N	0.88 (3)	C13—C17	1.385 (4)
N3—C12	1.268 (4)	C14—C15	1.363 (4)
N4—C16	1.314 (5)	C14—H14	0.93
N4—C17	1.332 (4)	C15—C16	1.368 (5)
C1—C2	1.383 (4)	C15—H15	0.93
C1—C10	1.505 (4)	C16—H16	0.93
C2—C3	1.377 (4)	C17—H17	0.93
C2—H2	0.93	O1W—H1W	0.83 (2)
C3—C4	1.429 (4)	O1W—H2W	0.81 (2)

C1—N1—C5	116.2 (2)	F2B—C10—F1A	63.3 (8)
C3—N2—N3	117.6 (3)	F3B—C10—F1A	77.7 (8)
C3—N2—H2N	124 (2)	F2A—C10—F1A	100.2 (4)
N3—N2—H2N	118 (2)	F3A—C10—F1B	46.4 (5)
C12—N3—N2	117.5 (3)	F2B—C10—F1B	97.8 (8)
C16—N4—C17	116.9 (3)	F3B—C10—F1B	91.8 (8)
N1—C1—C2	126.4 (3)	F2A—C10—F1B	69.6 (6)
N1—C1—C10	114.4 (2)	F1A—C10—F1B	140.0 (5)
C2—C1—C10	119.2 (3)	F3A—C10—C1	115.4 (3)
C3—C2—C1	118.5 (2)	F2B—C10—C1	111.6 (6)
C3—C2—H2	120.7	F3B—C10—C1	112.9 (7)
C1—C2—H2	120.7	F2A—C10—C1	110.3 (5)
N2—C3—C2	120.9 (3)	F1A—C10—C1	113.2 (3)
N2—C3—C4	120.8 (3)	F1B—C10—C1	106.5 (5)
C2—C3—C4	118.3 (2)	F4—C11—F5	105.5 (3)
C9—C4—C5	118.7 (2)	F4—C11—F6	105.0 (3)
C9—C4—C3	123.8 (3)	F5—C11—F6	106.7 (3)
C5—C4—C3	117.5 (2)	F4—C11—C6	113.9 (3)
N1—C5—C4	123.2 (2)	F5—C11—C6	112.9 (3)
N1—C5—C6	118.5 (2)	F6—C11—C6	112.1 (3)
C4—C5—C6	118.4 (3)	N3—C12—C13	120.0 (3)
C7—C6—C5	120.7 (3)	N3—C12—H12	120.0
C7—C6—C11	119.3 (3)	C13—C12—H12	120.0
C5—C6—C11	120.0 (3)	C14—C13—C17	116.4 (3)
C6—C7—C8	120.8 (3)	C14—C13—C12	123.3 (3)
C6—C7—H7	119.6	C17—C13—C12	120.3 (3)
C8—C7—H7	119.6	C15—C14—C13	119.6 (3)
C9—C8—C7	120.2 (3)	C15—C14—H14	120.2
C9—C8—H8	119.9	C13—C14—H14	120.2
C7—C8—H8	119.9	C14—C15—C16	119.1 (4)
C8—C9—C4	121.2 (3)	C14—C15—H15	120.5
C8—C9—H9	119.4	C16—C15—H15	120.5
C4—C9—H9	119.4	N4—C16—C15	123.6 (3)
F3A—C10—F2B	51.7 (6)	N4—C16—H16	118.2
F3A—C10—F3B	122.8 (7)	C15—C16—H16	118.2
F2B—C10—F3B	129.4 (10)	N4—C17—C13	124.5 (4)
F3A—C10—F2A	108.2 (6)	N4—C17—H17	117.8
F2B—C10—F2A	138.2 (7)	C13—C17—H17	117.8
F3B—C10—F2A	23.7 (8)	H1W—O1W—H2W	112 (4)
F3A—C10—F1A	108.5 (6)

C3—N2—N3—C12	173.2 (3)	N1—C1—C10—F3A	168.6 (8)
C5—N1—C1—C2	1.0 (5)	C2—C1—C10—F3A	−9.6 (9)
C5—N1—C1—C10	−177.1 (3)	N1—C1—C10—F2B	112.0 (9)
N1—C1—C2—C3	0.3 (5)	C2—C1—C10—F2B	−66.2 (10)
C10—C1—C2—C3	178.2 (3)	N1—C1—C10—F3B	−43.1 (9)
N3—N2—C3—C2	−7.4 (4)	C2—C1—C10—F3B	138.7 (8)
N3—N2—C3—C4	173.6 (3)	N1—C1—C10—F2A	−68.5 (5)
C1—C2—C3—N2	179.6 (3)	C2—C1—C10—F2A	113.3 (5)
C1—C2—C3—C4	−1.3 (4)	N1—C1—C10—F1A	42.9 (4)
N2—C3—C4—C9	0.1 (5)	C2—C1—C10—F1A	−135.3 (4)
C2—C3—C4—C9	−179.0 (3)	N1—C1—C10—F1B	−142.3 (6)
N2—C3—C4—C5	−179.9 (3)	C2—C1—C10—F1B	39.5 (7)
C2—C3—C4—C5	1.0 (4)	C7—C6—C11—F4	−120.2 (3)
C1—N1—C5—C4	−1.3 (4)	C5—C6—C11—F4	61.1 (4)
C1—N1—C5—C6	178.2 (3)	C7—C6—C11—F5	119.5 (4)
C9—C4—C5—N1	−179.7 (3)	C5—C6—C11—F5	−59.1 (4)
C3—C4—C5—N1	0.3 (4)	C7—C6—C11—F6	−1.1 (5)
C9—C4—C5—C6	0.8 (4)	C5—C6—C11—F6	−179.7 (3)
C3—C4—C5—C6	−179.1 (3)	N2—N3—C12—C13	176.9 (3)
N1—C5—C6—C7	179.1 (3)	N3—C12—C13—C14	−8.3 (5)
C4—C5—C6—C7	−1.4 (5)	N3—C12—C13—C17	170.9 (4)
N1—C5—C6—C11	−2.3 (4)	C17—C13—C14—C15	−0.3 (5)
C4—C5—C6—C11	177.2 (3)	C12—C13—C14—C15	179.0 (3)
C5—C6—C7—C8	1.1 (5)	C13—C14—C15—C16	1.0 (5)
C11—C6—C7—C8	−177.5 (3)	C17—N4—C16—C15	−0.5 (6)
C6—C7—C8—C9	−0.1 (6)	C14—C15—C16—N4	−0.6 (6)
C7—C8—C9—C4	−0.5 (5)	C16—N4—C17—C13	1.3 (6)
C5—C4—C9—C8	0.1 (5)	C14—C13—C17—N4	−0.9 (6)
C3—C4—C9—C8	−180.0 (3)	C12—C13—C17—N4	179.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.88 (3)	2.04 (3)	2.914 (5)	169 (3)
O1W—H1W···N4ⁱ	0.83 (5)	2.06 (6)	2.855 (5)	163 (7)
C9—H9···O1W	0.93	2.42	3.331 (5)	167

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀F₆N₄·H₂O
M_r	402.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	21.103 (4), 15.120 (3), 12.537 (3)
β (°)	118.633 (3)
V (Å³)	3511.1 (13)
Z	8
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
Absorption correction	ψ scan (SADABS; Bruker, 2001)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	13267, 3416, 2309
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.169, 1.04
No. of reflections	3416
No. of parameters	301
No. of restraints	54
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.88 (3)	2.04 (3)	2.914 (5)	169 (3)
O1W—H1W···N4ⁱ	0.83 (5)	2.06 (6)	2.855 (5)	163 (7)
C9—H9···O1W	0.93	2.42	3.331 (5)	167

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

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

References

Al-eryani, W. F. A., Kumari, J. S., Arunkashi, H. K., Vepuri, S. B. & Devarajegowda, H. C. (2010). Acta Cryst. E66, o1742. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 66| Part 9| September 2010| Pages o2237-o2238

https://doi.org/10.1107/S1600536810030862

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

Nicotinaldehyde [2,8-bis­­(tri­fluoro­meth­yl)quinolin-4-yl]hydrazone monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Nicotinaldehyde [2,8-bis(trifluoromethyl)quinolin-4-yl]hydrazone monohydrate