3-[(E)-(7-Chloro-4-quinol-yl)hydrazono-meth-yl]benzonitrile monohydrate.

The title monohydrate, C(17)H(11)ClN(4)·H(2)O, features an essentially planar organic mol-ecule, as seen in the dihedral angle of 2.42 (8)° formed between the quinoline and benzene planes. The conformation about the imine bond is E, and the N-H group is oriented towards the quinoline residue. The major feature of the crystal packing is the formation of supra-molecular chains along [100], whereby the water mol-ecule accepts one N-H⋯O hydrogen bond and makes two O-H⋯N hydrogen bonds. A C-H⋯O link is also present.

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 n class="Chemical">quinoline-based anti-malarials, see: Andrade et al. (2007 ▶); Cunico et al. (2006 ▶); da Silva et al. (2003 ▶); de Souza et al. (2005 ▶). For a related crystallographic study on neutral species related to the title compound, see: Kaiser et al. (2009 ▶).

Experimental

Crystal data

C17H11ClN4·H2O

M = 324.76

Triclinic,

a = 8.7406 (2) Å

b = 9.8587 (3) Å

c = 10.2301 (2) Å

α = 110.8897 (15)°

β = 93.4341 (16)°

γ = 110.6766 (15)°

V = 752.93 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.12 × 0.09 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.901, T max = 0.990

14600 measured reflections

3425 independent reflections

2902 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.109

S = 1.10

3425 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.25 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/S1600536809050120/hb5242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050120/hb5242Isup2.hkl

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

C17H11ClN4·H2O	Z = 2
Mr = 324.76	F(000) = 336
Triclinic, P1	Dx = 1.432 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7406 (2) Å	Cell parameters from 11816 reflections
b = 9.8587 (3) Å	θ = 2.9–27.5°
c = 10.2301 (2) Å	µ = 0.26 mm−1
α = 110.8897 (15)°	T = 120 K
β = 93.4341 (16)°	Plate, yellow
γ = 110.6766 (15)°	0.12 × 0.09 × 0.04 mm
V = 752.93 (3) Å3

Nonius KappaCCD area-detector diffractometer	3425 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2902 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.046
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→12
Tmin = 0.901, Tmax = 0.990	l = −13→13
14600 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.023P)2 + 0.7336P] where P = (Fo2 + 2Fc2)/3
3425 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.25 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	0.19140 (6)	0.44486 (6)	−0.08216 (5)	0.02503 (14)
N1	0.0883 (2)	0.39813 (19)	0.38535 (17)	0.0215 (3)
N2	0.49296 (19)	0.27107 (18)	0.43632 (17)	0.0181 (3)
H2N	0.559 (3)	0.270 (3)	0.377 (2)	0.022*
N3	0.52218 (19)	0.23502 (18)	0.55031 (16)	0.0181 (3)
N4	1.1329 (2)	0.0074 (2)	0.7938 (2)	0.0357 (5)
C1	0.1296 (2)	0.3704 (2)	0.4975 (2)	0.0217 (4)
H1	0.0635	0.3806	0.5679	0.026*
C2	0.2613 (2)	0.3278 (2)	0.5209 (2)	0.0204 (4)
H2	0.2816	0.3086	0.6036	0.024*
C3	0.3625 (2)	0.3139 (2)	0.42154 (19)	0.0164 (4)
C4	0.3262 (2)	0.3449 (2)	0.29879 (19)	0.0160 (4)
C5	0.4207 (2)	0.3368 (2)	0.1905 (2)	0.0191 (4)
H5	0.5150	0.3113	0.1983	0.023*
C6	0.3779 (2)	0.3654 (2)	0.0746 (2)	0.0203 (4)
H6	0.4411	0.3583	0.0019	0.024*
C7	0.2398 (2)	0.4052 (2)	0.0646 (2)	0.0194 (4)
C8	0.1449 (2)	0.4147 (2)	0.1657 (2)	0.0193 (4)
H8	0.0515	0.4409	0.1557	0.023*
C9	0.1869 (2)	0.3852 (2)	0.28647 (19)	0.0178 (4)
C10	0.6454 (2)	0.1947 (2)	0.5564 (2)	0.0197 (4)
H10	0.7095	0.1919	0.4844	0.024*
C11	0.6892 (2)	0.1527 (2)	0.67264 (19)	0.0192 (4)
C12	0.8252 (2)	0.1113 (2)	0.6757 (2)	0.0216 (4)
H12	0.8867	0.1086	0.6020	0.026*
C13	0.8715 (2)	0.0735 (2)	0.7873 (2)	0.0231 (4)
C14	0.7821 (3)	0.0759 (2)	0.8950 (2)	0.0286 (5)
H14	0.8144	0.0508	0.9708	0.034*
C15	0.6451 (3)	0.1154 (3)	0.8908 (2)	0.0298 (5)
H15	0.5829	0.1166	0.9640	0.036*
C16	0.5979 (3)	0.1531 (2)	0.7807 (2)	0.0240 (4)
H16	0.5034	0.1792	0.7786	0.029*
C17	1.0162 (3)	0.0351 (2)	0.7902 (2)	0.0275 (5)
O1W	0.74203 (19)	0.2487 (2)	0.26148 (16)	0.0261 (3)
H1W	0.746 (3)	0.160 (3)	0.231 (3)	0.039*
H2W	0.845 (4)	0.311 (3)	0.302 (3)	0.039*

	U11	U22	U33	U12	U13	U23
Cl1	0.0233 (2)	0.0305 (3)	0.0261 (3)	0.0115 (2)	0.00062 (18)	0.0168 (2)
N1	0.0203 (8)	0.0239 (8)	0.0255 (8)	0.0132 (7)	0.0078 (7)	0.0109 (7)
N2	0.0171 (8)	0.0231 (8)	0.0199 (8)	0.0113 (6)	0.0052 (6)	0.0115 (7)
N3	0.0198 (8)	0.0162 (7)	0.0177 (7)	0.0070 (6)	0.0004 (6)	0.0069 (6)
N4	0.0342 (10)	0.0308 (10)	0.0417 (11)	0.0172 (9)	−0.0047 (9)	0.0122 (9)
C1	0.0209 (9)	0.0243 (10)	0.0229 (9)	0.0116 (8)	0.0080 (8)	0.0097 (8)
C2	0.0210 (9)	0.0211 (9)	0.0201 (9)	0.0087 (8)	0.0031 (7)	0.0094 (8)
C3	0.0150 (8)	0.0130 (8)	0.0191 (9)	0.0044 (7)	0.0018 (7)	0.0055 (7)
C4	0.0144 (8)	0.0136 (8)	0.0195 (9)	0.0063 (7)	0.0021 (7)	0.0056 (7)
C5	0.0162 (9)	0.0211 (9)	0.0225 (9)	0.0100 (7)	0.0031 (7)	0.0094 (8)
C6	0.0182 (9)	0.0218 (9)	0.0223 (9)	0.0083 (8)	0.0049 (7)	0.0100 (8)
C7	0.0188 (9)	0.0179 (9)	0.0217 (9)	0.0067 (7)	−0.0013 (7)	0.0097 (7)
C8	0.0147 (8)	0.0189 (9)	0.0250 (9)	0.0084 (7)	0.0012 (7)	0.0085 (8)
C9	0.0153 (8)	0.0155 (8)	0.0212 (9)	0.0068 (7)	0.0020 (7)	0.0055 (7)
C10	0.0192 (9)	0.0211 (9)	0.0206 (9)	0.0089 (7)	0.0036 (7)	0.0095 (8)
C11	0.0207 (9)	0.0156 (8)	0.0191 (9)	0.0061 (7)	−0.0013 (7)	0.0066 (7)
C12	0.0212 (9)	0.0182 (9)	0.0236 (9)	0.0066 (8)	0.0017 (8)	0.0085 (8)
C13	0.0247 (10)	0.0163 (9)	0.0250 (10)	0.0077 (8)	−0.0045 (8)	0.0069 (8)
C14	0.0397 (12)	0.0246 (10)	0.0222 (10)	0.0140 (9)	−0.0016 (9)	0.0107 (8)
C15	0.0408 (12)	0.0311 (11)	0.0229 (10)	0.0172 (10)	0.0082 (9)	0.0138 (9)
C16	0.0272 (10)	0.0246 (10)	0.0230 (10)	0.0134 (8)	0.0045 (8)	0.0101 (8)
C17	0.0321 (11)	0.0200 (10)	0.0266 (10)	0.0093 (9)	−0.0053 (9)	0.0082 (8)
O1W	0.0213 (7)	0.0359 (8)	0.0266 (8)	0.0169 (7)	0.0065 (6)	0.0130 (7)

Cl1—C7	1.7454 (18)	C7—C8	1.362 (3)
N1—C1	1.328 (2)	C8—C9	1.423 (2)
N1—C9	1.368 (2)	C8—H8	0.9500
N2—C3	1.366 (2)	C10—C11	1.462 (2)
N2—N3	1.369 (2)	C10—H10	0.9500
N2—H2N	0.86 (2)	C11—C12	1.388 (3)
N3—C10	1.278 (2)	C11—C16	1.401 (3)
N4—C17	1.147 (3)	C12—C13	1.401 (3)
C1—C2	1.393 (3)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.386 (3)
C2—C3	1.389 (3)	C13—C17	1.444 (3)
C2—H2	0.9500	C14—C15	1.387 (3)
C3—C4	1.437 (2)	C14—H14	0.9500
C4—C5	1.417 (3)	C15—C16	1.389 (3)
C4—C9	1.419 (2)	C15—H15	0.9500
C5—C6	1.373 (3)	C16—H16	0.9500
C5—H5	0.9500	O1W—H1W	0.83 (3)
C6—C7	1.403 (3)	O1W—H2W	0.86 (3)
C6—H6	0.9500
C1—N1—C9	116.07 (16)	C9—C8—H8	120.3
C3—N2—N3	119.16 (15)	N1—C9—C4	123.72 (16)
C3—N2—H2N	121.4 (14)	N1—C9—C8	116.93 (16)
N3—N2—H2N	119.4 (14)	C4—C9—C8	119.35 (16)
C10—N3—N2	115.64 (16)	N3—C10—C11	120.96 (17)
N1—C1—C2	125.78 (18)	N3—C10—H10	119.5
N1—C1—H1	117.1	C11—C10—H10	119.5
C2—C1—H1	117.1	C12—C11—C16	119.17 (17)
C3—C2—C1	118.91 (17)	C12—C11—C10	118.91 (17)
C3—C2—H2	120.5	C16—C11—C10	121.92 (17)
C1—C2—H2	120.5	C11—C12—C13	120.01 (18)
N2—C3—C2	122.36 (16)	C11—C12—H12	120.0
N2—C3—C4	119.55 (16)	C13—C12—H12	120.0
C2—C3—C4	118.09 (16)	C14—C13—C12	120.63 (18)
C5—C4—C9	118.81 (16)	C14—C13—C17	120.38 (17)
C5—C4—C3	123.77 (16)	C12—C13—C17	118.98 (19)
C9—C4—C3	117.42 (16)	C13—C14—C15	119.29 (18)
C6—C5—C4	120.96 (17)	C13—C14—H14	120.4
C6—C5—H5	119.5	C15—C14—H14	120.4
C4—C5—H5	119.5	C14—C15—C16	120.6 (2)
C5—C6—C7	119.30 (18)	C14—C15—H15	119.7
C5—C6—H6	120.4	C16—C15—H15	119.7
C7—C6—H6	120.4	C15—C16—C11	120.31 (19)
C8—C7—C6	122.12 (17)	C15—C16—H16	119.8
C8—C7—Cl1	119.72 (14)	C11—C16—H16	119.8
C6—C7—Cl1	118.16 (15)	N4—C17—C13	178.8 (2)
C7—C8—C9	119.46 (16)	H1W—O1W—H2W	102 (2)
C7—C8—H8	120.3
C3—N2—N3—C10	179.41 (16)	C5—C4—C9—N1	−179.23 (17)
C9—N1—C1—C2	−1.0 (3)	C3—C4—C9—N1	1.1 (3)
N1—C1—C2—C3	0.9 (3)	C5—C4—C9—C8	0.6 (3)
N3—N2—C3—C2	2.4 (3)	C3—C4—C9—C8	−179.14 (16)
N3—N2—C3—C4	−177.19 (15)	C7—C8—C9—N1	179.30 (17)
C1—C2—C3—N2	−179.34 (17)	C7—C8—C9—C4	−0.5 (3)
C1—C2—C3—C4	0.2 (3)	N2—N3—C10—C11	−179.76 (16)
N2—C3—C4—C5	−1.2 (3)	N3—C10—C11—C12	−179.33 (17)
C2—C3—C4—C5	179.21 (17)	N3—C10—C11—C16	0.7 (3)
N2—C3—C4—C9	178.48 (16)	C16—C11—C12—C13	−1.2 (3)
C2—C3—C4—C9	−1.1 (2)	C10—C11—C12—C13	178.81 (17)
C9—C4—C5—C6	−0.7 (3)	C11—C12—C13—C14	0.4 (3)
C3—C4—C5—C6	178.94 (17)	C11—C12—C13—C17	−178.30 (17)
C4—C5—C6—C7	0.8 (3)	C12—C13—C14—C15	0.4 (3)
C5—C6—C7—C8	−0.8 (3)	C17—C13—C14—C15	179.10 (19)
C5—C6—C7—Cl1	178.69 (14)	C13—C14—C15—C16	−0.4 (3)
C6—C7—C8—C9	0.6 (3)	C14—C15—C16—C11	−0.4 (3)
Cl1—C7—C8—C9	−178.84 (14)	C12—C11—C16—C15	1.2 (3)
C1—N1—C9—C4	0.0 (3)	C10—C11—C16—C15	−178.82 (19)
C1—N1—C9—C8	−179.86 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N4i	0.83 (3)	2.21 (3)	2.982 (3)	155 (3)
O1w—H2w···N1ii	0.86 (3)	1.99 (3)	2.828 (3)	164 (3)
N2—H2n···O1w	0.86 (3)	2.07 (3)	2.917 (2)	167 (3)
C5—H5···O1w	0.95	2.39	3.331 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N4i	0.83 (3)	2.21 (3)	2.982 (3)	155 (3)
O1w—H2w⋯N1ii	0.86 (3)	1.99 (3)	2.828 (3)	164 (3)
N2—H2n⋯O1w	0.86 (3)	2.07 (3)	2.917 (2)	167 (3)
C5—H5⋯O1w	0.95	2.39	3.331 (3)	169

Symmetry codes: (i) ; (ii) .