(E)-N'-(2,4,5-Trifluorobenzyl-idene)isonicotinohydrazide monohydrate.

In the Schiff base mol-ecule of the title compound, C(13)H(8)F(3)N(3)O·H(2)O, the benzene ring and the pyridine ring are nearly coplanar, making a dihedral angle of 6.64 (7)°. The mol-ecule exists in an E configuration with respect to the C=N double bond. In the crystal structure, mol-ecules are linked via the water mol-ecules into two-dimensional planes parallel to the ab plane through inter-molecular N-H⋯O, O-H⋯O O-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For applications of isoniazid (isonicotinylhydrazine) derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Kahwa et al. (1986 ▶). For the preparation of the title compound, see: Lourenco et al. (2008 ▶). For related structures, see: Naveenkumar et al. (2009 ▶, 2010 ▶); Shi (2005 ▶).

Experimental

Crystal data

C13H8F3N3O·H2O

M = 297.24

Triclinic,

a = 4.9241 (1) Å

b = 6.3915 (1) Å

c = 21.3387 (2) Å

α = 88.616 (1)°

β = 86.556 (1)°

γ = 76.056 (1)°

V = 650.58 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.32 × 0.32 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.984

14710 measured reflections

4024 independent reflections

2730 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.146

S = 1.05

4024 reflections

230 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004514/sj2725sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004514/sj2725Isup2.hkl

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

C13H8F3N3O·H2O	Z = 2
Mr = 297.24	F(000) = 304
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9241 (1) Å	Cell parameters from 6031 reflections
b = 6.3915 (1) Å	θ = 2.9–30.8°
c = 21.3387 (2) Å	µ = 0.13 mm−1
α = 88.616 (1)°	T = 296 K
β = 86.556 (1)°	Plate, colourless
γ = 76.056 (1)°	0.32 × 0.32 × 0.13 mm
V = 650.58 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4024 independent reflections
Radiation source: fine-focus sealed tube	2730 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 30.8°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→7
Tmin = 0.958, Tmax = 0.984	k = −9→9
14710 measured reflections	l = −30→29

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0515P] where P = (Fo2 + 2Fc2)/3
4024 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 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
F1	1.20930 (18)	0.63383 (14)	0.34682 (4)	0.0667 (3)
F2	1.2581 (2)	1.19398 (18)	0.48033 (4)	0.0824 (3)
F3	0.8111 (2)	1.44958 (15)	0.42966 (5)	0.0834 (3)
O1	0.1646 (2)	1.24750 (13)	0.19113 (5)	0.0552 (3)
N1	0.5532 (2)	1.00798 (15)	0.25981 (4)	0.0386 (2)
N2	0.4249 (2)	0.91747 (15)	0.21550 (4)	0.0377 (2)
N3	−0.1882 (3)	0.7926 (2)	0.04246 (6)	0.0592 (3)
C1	1.1071 (3)	0.8366 (2)	0.36730 (6)	0.0431 (3)
C2	1.2389 (3)	0.9080 (3)	0.41488 (6)	0.0532 (3)
C3	1.1375 (3)	1.1151 (3)	0.43436 (6)	0.0533 (3)
C4	0.9082 (3)	1.2479 (2)	0.40781 (6)	0.0520 (3)
C5	0.7792 (3)	1.1753 (2)	0.36057 (6)	0.0465 (3)
C6	0.8779 (2)	0.96531 (19)	0.33900 (5)	0.0381 (3)
C7	0.7429 (2)	0.87952 (19)	0.28944 (5)	0.0391 (3)
C8	0.2279 (2)	1.05161 (17)	0.18276 (5)	0.0381 (3)
C9	0.0888 (2)	0.95209 (18)	0.13457 (5)	0.0381 (3)
C10	−0.1271 (3)	1.0858 (2)	0.10359 (6)	0.0469 (3)
C11	−0.2587 (3)	0.9994 (3)	0.05883 (6)	0.0549 (3)
C12	0.0208 (4)	0.6670 (3)	0.07203 (7)	0.0645 (4)
C13	0.1642 (3)	0.7368 (2)	0.11825 (7)	0.0555 (4)
O1W	0.6042 (3)	0.46898 (15)	0.22162 (5)	0.0567 (3)
H2A	1.388 (4)	0.807 (3)	0.4315 (9)	0.079 (5)*
H5A	0.619 (4)	1.275 (3)	0.3436 (8)	0.069 (5)*
H7A	0.798 (3)	0.727 (2)	0.2805 (7)	0.054 (4)*
H10A	−0.178 (3)	1.237 (3)	0.1110 (7)	0.061 (4)*
H11A	−0.398 (4)	1.092 (3)	0.0388 (8)	0.069 (5)*
H12A	0.087 (4)	0.519 (3)	0.0585 (9)	0.084 (6)*
H13A	0.316 (4)	0.636 (3)	0.1371 (8)	0.073 (5)*
H1N2	0.479 (3)	0.776 (3)	0.2116 (8)	0.067 (5)*
H1W1	0.759 (4)	0.402 (3)	0.2127 (8)	0.071 (6)*
H2W1	0.499 (4)	0.384 (4)	0.2232 (10)	0.099 (7)*

	U11	U22	U33	U12	U13	U23
F1	0.0610 (5)	0.0571 (5)	0.0724 (6)	0.0110 (4)	−0.0253 (4)	−0.0153 (4)
F2	0.0779 (6)	0.1120 (8)	0.0649 (6)	−0.0278 (6)	−0.0330 (5)	−0.0306 (5)
F3	0.0999 (8)	0.0612 (5)	0.0897 (7)	−0.0114 (5)	−0.0295 (6)	−0.0347 (5)
O1	0.0565 (6)	0.0337 (4)	0.0772 (6)	−0.0068 (4)	−0.0346 (5)	−0.0034 (4)
N1	0.0405 (5)	0.0378 (5)	0.0402 (5)	−0.0114 (4)	−0.0145 (4)	−0.0050 (4)
N2	0.0408 (5)	0.0331 (5)	0.0412 (5)	−0.0087 (4)	−0.0177 (4)	−0.0039 (4)
N3	0.0653 (8)	0.0712 (8)	0.0501 (6)	−0.0285 (6)	−0.0241 (5)	−0.0041 (6)
C1	0.0381 (6)	0.0491 (7)	0.0410 (6)	−0.0062 (5)	−0.0103 (5)	−0.0040 (5)
C2	0.0407 (7)	0.0730 (9)	0.0446 (7)	−0.0073 (6)	−0.0172 (5)	−0.0031 (6)
C3	0.0490 (7)	0.0758 (9)	0.0409 (6)	−0.0220 (7)	−0.0140 (5)	−0.0131 (6)
C4	0.0593 (8)	0.0503 (7)	0.0499 (7)	−0.0161 (6)	−0.0125 (6)	−0.0129 (5)
C5	0.0492 (7)	0.0431 (6)	0.0480 (7)	−0.0086 (5)	−0.0183 (5)	−0.0049 (5)
C6	0.0377 (6)	0.0422 (6)	0.0367 (5)	−0.0119 (4)	−0.0110 (4)	−0.0020 (4)
C7	0.0411 (6)	0.0361 (5)	0.0415 (6)	−0.0091 (4)	−0.0139 (5)	−0.0039 (4)
C8	0.0372 (6)	0.0355 (5)	0.0442 (6)	−0.0107 (4)	−0.0138 (5)	−0.0013 (4)
C9	0.0378 (6)	0.0433 (6)	0.0375 (6)	−0.0153 (5)	−0.0126 (4)	−0.0005 (4)
C10	0.0449 (7)	0.0509 (7)	0.0451 (7)	−0.0084 (5)	−0.0161 (5)	−0.0017 (5)
C11	0.0484 (7)	0.0724 (9)	0.0459 (7)	−0.0138 (7)	−0.0216 (6)	0.0011 (6)
C12	0.0858 (11)	0.0528 (8)	0.0630 (9)	−0.0250 (8)	−0.0335 (8)	−0.0060 (7)
C13	0.0671 (9)	0.0427 (7)	0.0603 (8)	−0.0132 (6)	−0.0322 (7)	−0.0036 (6)
O1W	0.0608 (7)	0.0322 (4)	0.0771 (7)	−0.0067 (4)	−0.0194 (5)	−0.0063 (4)

F1—C1	1.3454 (15)	C5—C6	1.3922 (17)
F2—C3	1.3445 (13)	C5—H5A	0.969 (18)
F3—C4	1.3463 (16)	C6—C7	1.4660 (14)
O1—C8	1.2299 (13)	C7—H7A	0.965 (15)
N1—C7	1.2737 (15)	C8—C9	1.5025 (14)
N1—N2	1.3791 (11)	C9—C13	1.3835 (17)
N2—C8	1.3477 (14)	C9—C10	1.3843 (17)
N2—H1N2	0.881 (18)	C10—C11	1.3821 (17)
N3—C12	1.326 (2)	C10—H10A	0.953 (16)
N3—C11	1.3324 (19)	C11—H11A	0.911 (19)
C1—C2	1.3800 (17)	C12—C13	1.3882 (17)
C1—C6	1.3877 (16)	C12—H12A	0.966 (19)
C2—C3	1.363 (2)	C13—H13A	0.963 (18)
C2—H2A	0.93 (2)	O1W—H1W1	0.79 (2)
C3—C4	1.381 (2)	O1W—H2W1	0.83 (2)
C4—C5	1.3699 (16)
C7—N1—N2	116.55 (9)	N1—C7—C6	118.93 (10)
C8—N2—N1	117.36 (9)	N1—C7—H7A	121.8 (9)
C8—N2—H1N2	126.2 (11)	C6—C7—H7A	119.2 (9)
N1—N2—H1N2	116.5 (11)	O1—C8—N2	122.04 (9)
C12—N3—C11	116.24 (11)	O1—C8—C9	120.84 (10)
F1—C1—C2	118.25 (11)	N2—C8—C9	117.12 (9)
F1—C1—C6	118.70 (10)	C13—C9—C10	117.67 (10)
C2—C1—C6	123.04 (12)	C13—C9—C8	124.60 (10)
C3—C2—C1	117.80 (12)	C10—C9—C8	117.72 (10)
C3—C2—H2A	126.1 (11)	C11—C10—C9	119.15 (12)
C1—C2—H2A	116.1 (11)	C11—C10—H10A	119.8 (9)
F2—C3—C2	120.48 (12)	C9—C10—H10A	121.0 (9)
F2—C3—C4	118.53 (13)	N3—C11—C10	123.93 (13)
C2—C3—C4	120.99 (11)	N3—C11—H11A	119.1 (11)
F3—C4—C5	120.41 (12)	C10—C11—H11A	116.9 (11)
F3—C4—C3	118.89 (11)	N3—C12—C13	124.42 (14)
C5—C4—C3	120.70 (12)	N3—C12—H12A	117.9 (11)
C4—C5—C6	120.06 (12)	C13—C12—H12A	117.5 (11)
C4—C5—H5A	117.3 (10)	C9—C13—C12	118.58 (13)
C6—C5—H5A	122.7 (10)	C9—C13—H13A	121.8 (10)
C1—C6—C5	117.41 (10)	C12—C13—H13A	119.6 (10)
C1—C6—C7	120.67 (11)	H1W1—O1W—H2W1	108.0 (19)
C5—C6—C7	121.89 (10)
C7—N1—N2—C8	−178.64 (11)	N2—N1—C7—C6	−177.37 (10)
F1—C1—C2—C3	178.60 (12)	C1—C6—C7—N1	−172.44 (12)
C6—C1—C2—C3	−0.2 (2)	C5—C6—C7—N1	9.12 (19)
C1—C2—C3—F2	−179.70 (12)	N1—N2—C8—O1	0.66 (18)
C1—C2—C3—C4	0.8 (2)	N1—N2—C8—C9	−179.99 (9)
F2—C3—C4—F3	−1.2 (2)	O1—C8—C9—C13	174.03 (13)
C2—C3—C4—F3	178.33 (14)	N2—C8—C9—C13	−5.32 (19)
F2—C3—C4—C5	179.61 (13)	O1—C8—C9—C10	−4.90 (18)
C2—C3—C4—C5	−0.8 (2)	N2—C8—C9—C10	175.74 (11)
F3—C4—C5—C6	−178.86 (13)	C13—C9—C10—C11	0.8 (2)
C3—C4—C5—C6	0.3 (2)	C8—C9—C10—C11	179.78 (12)
F1—C1—C6—C5	−179.11 (12)	C12—N3—C11—C10	0.3 (2)
C2—C1—C6—C5	−0.3 (2)	C9—C10—C11—N3	−1.0 (2)
F1—C1—C6—C7	2.38 (18)	C11—N3—C12—C13	0.7 (3)
C2—C1—C6—C7	−178.84 (12)	C10—C9—C13—C12	0.1 (2)
C4—C5—C6—C1	0.3 (2)	C8—C9—C13—C12	−178.85 (13)
C4—C5—C6—C7	178.75 (12)	N3—C12—C13—C9	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1W	0.883 (19)	1.921 (19)	2.7910 (13)	168.1 (16)
O1W—H1W1···O1i	0.79 (2)	2.03 (2)	2.8263 (17)	176.3 (18)
O1W—H2W1···O1ii	0.84 (2)	2.19 (2)	2.9670 (17)	155 (2)
O1W—H2W1···N1ii	0.84 (2)	2.47 (2)	3.1024 (14)	133.7 (19)
C7—H7A···O1W	0.967 (13)	2.492 (14)	3.2576 (16)	135.9 (12)
C13—H13A···O1W	0.963 (19)	2.427 (18)	3.3308 (19)	156.2 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1W	0.883 (19)	1.921 (19)	2.7910 (13)	168.1 (16)
O1W—H1W1⋯O1i	0.79 (2)	2.03 (2)	2.8263 (17)	176.3 (18)
O1W—H2W1⋯O1ii	0.84 (2)	2.19 (2)	2.9670 (17)	155 (2)
O1W—H2W1⋯N1ii	0.84 (2)	2.47 (2)	3.1024 (14)	133.7 (19)
C7—H7A⋯O1W	0.967 (13)	2.492 (14)	3.2576 (16)	135.9 (12)
C13—H13A⋯O1W	0.963 (19)	2.427 (18)	3.3308 (19)	156.2 (14)

Symmetry codes: (i) ; (ii) .