7-Chloro-4-[(E)-N'-(4-fluoro-benzyl-idene)hydrazin-yl]quinoline monohydrate.

The mol-ecule of the title hydrate, C(16)H(11)ClFN(3)·H(2)O, is slightly twisted, as indicated by the dihedral angle of 9.55 (10)° formed between the quinoline ring system and the benzene ring. The conformation about the C=N double bond is E, and the amine-H atom is oriented towards the quinoline residue. In the crystal structure, the water mol-ecule accepts an N-H⋯O and makes two O-H⋯N(quinoline) hydrogen bonds, generating a two-dimensional array in the ab plane, which is further stabilized by C-H⋯O inter-actions. The most significant contacts between layers are of the type C-H⋯F.

Related literature

For background information on the pharmacological activity of quinoline derivatives, see: Elslager et al. (1969 ▶); Font et al. (1997 ▶); Kaminsky & Meltzer (1968 ▶); Musiol et al. (2006 ▶); Nakamura et al. (1999 ▶); Palmer et al. (1993 ▶); Ridley (2002 ▶); Sloboda et al. (1991 ▶); Tanenbaum & Tuffanelli (1980 ▶); Warshakoon et al. (2006 ▶). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007 ▶); Cunico et al. (2006 ▶); da Silva et al. (2003 ▶); de Souza et al. (2005 ▶). For crystallographic studies on mol­ecules related to the title compound, see: Kaiser et al. (2009 ▶); de Souza et al. (2009 ▶); de Ferreira et al. (2009 ▶). For the synthesis, see: Pellerano et al. (1976 ▶).

Experimental

Crystal data

C16H11ClFN3·H2O

M = 317.74

Monoclinic,

a = 3.7795 (2) Å

b = 15.4188 (11) Å

c = 24.8576 (16) Å

β = 90.286 (4)°

V = 1448.57 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 120 K

0.90 × 0.04 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.614, T max = 0.746

19494 measured reflections

3291 independent reflections

2009 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.131

S = 1.04

3291 reflections

205 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053367/lh2970sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053367/lh2970Isup2.hkl

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

C16H11ClFN3·H2O	F(000) = 656
Mr = 317.74	Dx = 1.457 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13530 reflections
a = 3.7795 (2) Å	θ = 2.9–27.5°
b = 15.4188 (11) Å	µ = 0.28 mm−1
c = 24.8576 (16) Å	T = 120 K
β = 90.286 (4)°	Needle, colourless
V = 1448.57 (16) Å3	0.90 × 0.04 × 0.04 mm
Z = 4

Enraf–Nonius KappaCCD area-detector diffractometer	3291 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2009 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.098
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −20→19
Tmin = 0.614, Tmax = 0.746	l = −32→32
19494 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.5902P] where P = (Fo2 + 2Fc2)/3
3291 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.33 e Å−3
3 restraints	Δρmin = −0.37 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.85154 (18)	−0.01273 (5)	0.43677 (3)	0.0319 (2)
F1	0.1997 (4)	0.22958 (11)	−0.11624 (6)	0.0367 (5)
N1	0.3942 (5)	−0.13713 (14)	0.26095 (9)	0.0214 (5)
N2	0.6585 (5)	0.08516 (14)	0.17189 (8)	0.0221 (5)
H2N	0.7847	0.1268	0.1867	0.027*
N3	0.5476 (5)	0.09163 (15)	0.11914 (8)	0.0212 (5)
C1	0.3270 (7)	−0.12969 (18)	0.20855 (11)	0.0225 (6)
H1	0.2176	−0.1776	0.1911	0.027*
C2	0.4043 (6)	−0.05737 (18)	0.17733 (10)	0.0210 (6)
H2	0.3436	−0.0566	0.1402	0.025*
C3	0.5701 (6)	0.01357 (17)	0.20052 (10)	0.0178 (6)
C4	0.6457 (6)	0.01003 (16)	0.25750 (10)	0.0176 (6)
C5	0.8024 (6)	0.07868 (18)	0.28696 (11)	0.0210 (6)
H5	0.8680	0.1303	0.2687	0.025*
C6	0.8613 (6)	0.07213 (18)	0.34118 (10)	0.0220 (6)
H6	0.9655	0.1189	0.3605	0.026*
C7	0.7663 (7)	−0.00432 (18)	0.36790 (11)	0.0218 (6)
C8	0.6151 (6)	−0.07217 (18)	0.34132 (10)	0.0214 (6)
H8	0.5531	−0.1233	0.3604	0.026*
C9	0.5501 (6)	−0.06654 (16)	0.28533 (10)	0.0179 (6)
C10	0.6205 (7)	0.16293 (18)	0.09495 (11)	0.0219 (6)
H10	0.7507	0.2064	0.1136	0.026*
C11	0.5085 (7)	0.17884 (18)	0.03962 (11)	0.0216 (6)
C12	0.3483 (7)	0.11448 (18)	0.00825 (11)	0.0231 (6)
H12	0.3087	0.0586	0.0232	0.028*
C13	0.2471 (7)	0.13101 (18)	−0.04411 (11)	0.0237 (6)
H13	0.1409	0.0871	−0.0656	0.028*
C14	0.3041 (7)	0.21294 (19)	−0.06453 (11)	0.0256 (7)
C15	0.4572 (7)	0.27824 (19)	−0.03525 (11)	0.0269 (7)
H15	0.4911	0.3342	−0.0504	0.032*
C16	0.5614 (7)	0.26028 (18)	0.01715 (11)	0.0232 (6)
H16	0.6708	0.3044	0.0380	0.028*
O1W	0.0566 (5)	0.23633 (12)	0.20098 (8)	0.0287 (5)
H1W	0.262 (3)	0.2503 (17)	0.2111 (12)	0.043*
H2W	−0.086 (5)	0.2775 (13)	0.2069 (12)	0.043*

	U11	U22	U33	U12	U13	U23
Cl1	0.0381 (4)	0.0386 (5)	0.0191 (4)	−0.0007 (3)	−0.0065 (3)	−0.0001 (3)
F1	0.0475 (10)	0.0422 (11)	0.0205 (9)	0.0086 (8)	−0.0082 (8)	0.0037 (8)
N1	0.0218 (12)	0.0225 (13)	0.0200 (13)	0.0000 (10)	−0.0006 (9)	−0.0006 (10)
N2	0.0269 (12)	0.0218 (13)	0.0177 (12)	−0.0046 (10)	−0.0046 (9)	0.0001 (10)
N3	0.0219 (12)	0.0265 (14)	0.0153 (12)	0.0018 (10)	−0.0022 (9)	0.0005 (10)
C1	0.0185 (14)	0.0204 (16)	0.0286 (17)	0.0005 (11)	−0.0024 (12)	−0.0026 (13)
C2	0.0204 (14)	0.0270 (16)	0.0156 (14)	0.0007 (12)	−0.0052 (11)	−0.0005 (12)
C3	0.0150 (13)	0.0189 (15)	0.0195 (14)	0.0014 (11)	−0.0008 (10)	−0.0011 (12)
C4	0.0151 (13)	0.0168 (14)	0.0209 (14)	0.0033 (11)	−0.0002 (10)	−0.0018 (12)
C5	0.0204 (14)	0.0189 (15)	0.0237 (15)	0.0012 (11)	0.0001 (11)	−0.0018 (12)
C6	0.0242 (15)	0.0210 (16)	0.0208 (15)	−0.0003 (12)	−0.0035 (11)	−0.0059 (12)
C7	0.0204 (14)	0.0276 (17)	0.0175 (14)	0.0030 (12)	−0.0016 (11)	−0.0034 (12)
C8	0.0198 (14)	0.0223 (16)	0.0220 (15)	0.0050 (12)	−0.0007 (11)	0.0046 (12)
C9	0.0154 (13)	0.0149 (14)	0.0233 (15)	0.0003 (11)	−0.0026 (10)	−0.0030 (12)
C10	0.0222 (15)	0.0215 (16)	0.0221 (16)	0.0019 (12)	0.0000 (11)	−0.0046 (13)
C11	0.0185 (14)	0.0253 (16)	0.0209 (15)	0.0030 (12)	0.0004 (11)	0.0010 (12)
C12	0.0261 (15)	0.0194 (15)	0.0238 (16)	−0.0004 (12)	0.0010 (12)	−0.0001 (12)
C13	0.0240 (15)	0.0241 (16)	0.0229 (16)	0.0009 (12)	−0.0018 (12)	−0.0045 (13)
C14	0.0273 (15)	0.0350 (18)	0.0145 (14)	0.0051 (13)	−0.0025 (11)	0.0012 (13)
C15	0.0265 (15)	0.0256 (17)	0.0287 (17)	0.0025 (13)	−0.0004 (12)	0.0043 (13)
C16	0.0244 (15)	0.0240 (16)	0.0213 (15)	−0.0016 (12)	−0.0012 (11)	−0.0037 (13)
O1W	0.0255 (11)	0.0227 (11)	0.0377 (13)	−0.0003 (9)	−0.0020 (9)	−0.0045 (9)

Cl1—C7	1.745 (3)	C6—H6	0.9500
F1—C14	1.367 (3)	C7—C8	1.362 (4)
N1—C1	1.331 (3)	C8—C9	1.414 (3)
N1—C9	1.377 (3)	C8—H8	0.9500
N2—C3	1.356 (3)	C10—C11	1.458 (4)
N2—N3	1.378 (3)	C10—H10	0.9500
N2—H2N	0.8800	C11—C16	1.389 (4)
N3—C10	1.284 (3)	C11—C12	1.398 (4)
C1—C2	1.390 (4)	C12—C13	1.379 (4)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.385 (4)	C13—C14	1.379 (4)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.445 (3)	C14—C15	1.369 (4)
C4—C5	1.415 (4)	C15—C16	1.387 (4)
C4—C9	1.416 (4)	C15—H15	0.9500
C5—C6	1.369 (3)	C16—H16	0.9500
C5—H5	0.9500	O1W—H1W	0.841 (10)
C6—C7	1.401 (4)	O1W—H2W	0.845 (10)
C1—N1—C9	116.2 (2)	C7—C8—H8	120.0
C3—N2—N3	118.9 (2)	C9—C8—H8	120.0
C3—N2—H2N	120.5	N1—C9—C8	117.2 (2)
N3—N2—H2N	120.5	N1—C9—C4	123.6 (2)
C10—N3—N2	116.3 (2)	C8—C9—C4	119.2 (2)
N1—C1—C2	125.2 (3)	N3—C10—C11	121.6 (2)
N1—C1—H1	117.4	N3—C10—H10	119.2
C2—C1—H1	117.4	C11—C10—H10	119.2
C3—C2—C1	119.8 (2)	C16—C11—C12	118.7 (2)
C3—C2—H2	120.1	C16—C11—C10	119.3 (2)
C1—C2—H2	120.1	C12—C11—C10	122.0 (3)
N2—C3—C2	122.4 (2)	C13—C12—C11	120.8 (3)
N2—C3—C4	119.8 (2)	C13—C12—H12	119.6
C2—C3—C4	117.7 (2)	C11—C12—H12	119.6
C5—C4—C9	118.5 (2)	C12—C13—C14	118.3 (3)
C5—C4—C3	124.0 (2)	C12—C13—H13	120.9
C9—C4—C3	117.4 (2)	C14—C13—H13	120.9
C6—C5—C4	121.3 (3)	F1—C14—C15	118.8 (3)
C6—C5—H5	119.3	F1—C14—C13	118.3 (2)
C4—C5—H5	119.3	C15—C14—C13	123.0 (3)
C5—C6—C7	119.2 (2)	C14—C15—C16	118.0 (3)
C5—C6—H6	120.4	C14—C15—H15	121.0
C7—C6—H6	120.4	C16—C15—H15	121.0
C8—C7—C6	121.6 (2)	C15—C16—C11	121.2 (3)
C8—C7—Cl1	119.6 (2)	C15—C16—H16	119.4
C6—C7—Cl1	118.8 (2)	C11—C16—H16	119.4
C7—C8—C9	120.0 (2)	H1W—O1W—H2W	110.0 (16)
C3—N2—N3—C10	176.0 (2)	C7—C8—C9—N1	−179.5 (2)
C9—N1—C1—C2	0.5 (4)	C7—C8—C9—C4	0.3 (4)
N1—C1—C2—C3	1.3 (4)	C5—C4—C9—N1	179.6 (2)
N3—N2—C3—C2	6.9 (4)	C3—C4—C9—N1	0.7 (4)
N3—N2—C3—C4	−172.4 (2)	C5—C4—C9—C8	−0.2 (3)
C1—C2—C3—N2	178.6 (2)	C3—C4—C9—C8	−179.1 (2)
C1—C2—C3—C4	−2.0 (4)	N2—N3—C10—C11	−178.2 (2)
N2—C3—C4—C5	1.6 (4)	N3—C10—C11—C16	173.3 (2)
C2—C3—C4—C5	−177.7 (2)	N3—C10—C11—C12	−6.6 (4)
N2—C3—C4—C9	−179.5 (2)	C16—C11—C12—C13	0.5 (4)
C2—C3—C4—C9	1.1 (3)	C10—C11—C12—C13	−179.5 (2)
C9—C4—C5—C6	−0.1 (4)	C11—C12—C13—C14	−0.8 (4)
C3—C4—C5—C6	178.7 (2)	C12—C13—C14—F1	−179.2 (2)
C4—C5—C6—C7	0.4 (4)	C12—C13—C14—C15	0.2 (4)
C5—C6—C7—C8	−0.3 (4)	F1—C14—C15—C16	180.0 (2)
C5—C6—C7—Cl1	178.65 (19)	C13—C14—C15—C16	0.5 (4)
C6—C7—C8—C9	0.0 (4)	C14—C15—C16—C11	−0.8 (4)
Cl1—C7—C8—C9	−178.98 (18)	C12—C11—C16—C15	0.2 (4)
C1—N1—C9—C8	178.3 (2)	C10—C11—C16—C15	−179.7 (2)
C1—N1—C9—C4	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1i	0.843 (16)	2.28 (2)	2.999 (3)	144 (2)
O1w—H2w···N1ii	0.85 (2)	1.93 (2)	2.761 (3)	166 (3)
N2—H2n···O1wiii	0.88	2.01	2.865 (3)	165
C5—H5···O1wiii	0.95	2.45	3.379 (3)	164
C10—H10···O1wiii	0.95	2.50	3.302 (3)	142
C1—H1···F1iv	0.95	2.56	3.399 (3)	147
C6—H6···F1v	0.95	2.56	3.477 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N1i	0.84 (2)	2.28 (2)	2.999 (3)	144 (2)
O1w—H2w⋯N1ii	0.85 (2)	1.93 (2)	2.761 (3)	166 (3)
N2—H2n⋯O1wiii	0.88	2.01	2.865 (3)	165
C5—H5⋯O1wiii	0.95	2.45	3.379 (3)	164
C10—H10⋯O1wiii	0.95	2.50	3.302 (3)	142
C1—H1⋯F1iv	0.95	2.56	3.399 (3)	147
C6—H6⋯F1v	0.95	2.56	3.477 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .