Nicotinaldehyde [2,8-bis-(trifluoro-meth-yl)quinolin-4-yl]hydrazone monohydrate.

In the title compound, C(17)H(10)F(6)N(4)·H(2)O, 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 trifluoro-methyl group is disordered over two orientations with occupancies of 0.70 (1) and 0.30 (1). The water mol-ecule is disordered over two positions with occupancies of 0.76 (1) and 0.24 (1). In the crystal, the water mol-ecule is linked to the main mol-ecule 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 inter-action 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 = 402.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.169

S = 1.04

3416 reflections

301 parameters

54 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.25 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 and PLATON (Spek, 2009 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030862/ci5125Isup2.hkl

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

C17H10F6N4·H2O	F(000) = 1632
Mr = 402.31	Dx = 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

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

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(Fo2) + (0.0764P)2 + 2.423P] where P = (Fo2 + 2Fc2)/3
3416 reflections	(Δ/σ)max = 0.001
301 parameters	Δρmax = 0.26 e Å−3
54 restraints	Δρmin = −0.25 e Å−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 > 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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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)

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

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) .