7-Chloro-4-[(E)-2-(4-methoxy-benzyl-idene)hydrazin-1-yl]quinoline monohydrate.

The organic mol-ecule in the title hydrate, C(17)H(14)ClN(3)O·H(2)O, has a small but significant twist from planarity, as seen in the dihedral angle of 12.10 (17)° between the quinoline and benzene rings. The conformation about the C=N bond is E. Chains along the b axis are formed in the crystal structure aided by water-quinoline O-H⋯N (× 2) and hydrazone-water N-H⋯O hydrogen bonds. Layers of these chains stack along the a axis via C-H⋯π and π-π inter-actions [ring centroid-ring centroid distance = 3.674 (2) Å]. C-H⋯O inter-actions are also present.

Related literature

For background to the pharmacological activity of quinoline derivatives, see: Warshakoon et al. (2006 ▶). For recent studies into quinoline-based anti-malarials, see: Andrade et al. (2007 ▶); de Souza et al. (2005 ▶). For related structures, see: Kaiser et al. (2009 ▶); de Souza et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C17H14ClN3O·H2O

M = 329.78

Triclinic,

a = 7.0086 (6) Å

b = 9.2384 (8) Å

c = 13.3701 (12) Å

α = 100.026 (4)°

β = 103.903 (5)°

γ = 107.000 (5)°

V = 775.27 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.12 × 0.04 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.686, T max = 1.000

10514 measured reflections

2702 independent reflections

2037 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.150

S = 1.02

2702 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DEn class="Chemical">NZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006598/lh5002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006598/lh5002Isup2.hkl

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

C17H14ClN3O·H2O	Z = 2
Mr = 329.78	F(000) = 344
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0086 (6) Å	Cell parameters from 27436 reflections
b = 9.2384 (8) Å	θ = 2.9–27.5°
c = 13.3701 (12) Å	µ = 0.26 mm−1
α = 100.026 (4)°	T = 120 K
β = 103.903 (5)°	Needle, colourless
γ = 107.000 (5)°	0.12 × 0.04 × 0.02 mm
V = 775.27 (12) Å3

Nonius KappaCCD area-detector diffractometer	2702 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2037 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.064
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.1°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −10→10
Tmin = 0.686, Tmax = 1.000	l = −15→15
10514 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0109P)2 + 2.93P] where P = (Fo2 + 2Fc2)/3
2702 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.36 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	0.12492 (19)	0.53097 (12)	0.13214 (8)	0.0337 (3)
O1	0.3226 (4)	0.0839 (3)	1.1296 (2)	0.0268 (7)
N1	0.2963 (5)	0.7665 (4)	0.5289 (2)	0.0233 (7)
N2	0.2484 (5)	0.3358 (4)	0.6035 (2)	0.0226 (7)
H2N	0.2193	0.2506	0.5527	0.027*
N3	0.2774 (5)	0.3291 (4)	0.7081 (2)	0.0220 (7)
C1	0.3251 (6)	0.7500 (4)	0.6279 (3)	0.0247 (9)
H1	0.3611	0.8418	0.6835	0.030*
C2	0.3074 (6)	0.6112 (4)	0.6569 (3)	0.0217 (9)
H2	0.3239	0.6092	0.7292	0.026*
C3	0.2653 (6)	0.4750 (4)	0.5796 (3)	0.0178 (8)
C4	0.2376 (6)	0.4842 (4)	0.4712 (3)	0.0188 (8)
C5	0.2011 (6)	0.3562 (4)	0.3853 (3)	0.0203 (8)
H5	0.1959	0.2576	0.3985	0.024*
C6	0.1728 (6)	0.3715 (4)	0.2828 (3)	0.0215 (8)
H6	0.1518	0.2852	0.2259	0.026*
C7	0.1753 (6)	0.5170 (4)	0.2634 (3)	0.0211 (8)
C8	0.2147 (6)	0.6443 (4)	0.3441 (3)	0.0225 (9)
H8	0.2180	0.7417	0.3292	0.027*
C9	0.2507 (6)	0.6313 (4)	0.4502 (3)	0.0201 (8)
C10	0.2358 (6)	0.1919 (5)	0.7224 (3)	0.0235 (9)
H10	0.1879	0.1044	0.6620	0.028*
C11	0.2591 (6)	0.1642 (4)	0.8281 (3)	0.0199 (8)
C12	0.2046 (6)	0.0122 (4)	0.8385 (3)	0.0222 (9)
H12	0.1524	−0.0724	0.7759	0.027*
C13	0.2235 (6)	−0.0212 (4)	0.9368 (3)	0.0214 (8)
H13	0.1854	−0.1267	0.9415	0.026*
C14	0.2985 (6)	0.1016 (4)	1.0276 (3)	0.0217 (8)
C15	0.3569 (6)	0.2567 (4)	1.0201 (3)	0.0229 (9)
H15	0.4099	0.3408	1.0830	0.027*
C16	0.3379 (6)	0.2878 (4)	0.9220 (3)	0.0227 (9)
H16	0.3781	0.3934	0.9176	0.027*
C17	0.2580 (7)	−0.0735 (4)	1.1403 (3)	0.0268 (9)
H17A	0.1093	−0.1280	1.0997	0.040*
H17B	0.2787	−0.0709	1.2158	0.040*
H17C	0.3418	−0.1291	1.1127	0.040*
O1W	0.7337 (5)	0.9550 (3)	0.5298 (2)	0.0309 (7)
H1W	0.736 (8)	1.039 (6)	0.511 (4)	0.046*
H2W	0.610 (8)	0.908 (6)	0.530 (4)	0.046*

	U11	U22	U33	U12	U13	U23
Cl1	0.0524 (7)	0.0299 (6)	0.0200 (5)	0.0158 (5)	0.0098 (5)	0.0088 (4)
O1	0.0346 (17)	0.0247 (15)	0.0202 (14)	0.0082 (13)	0.0077 (12)	0.0084 (11)
N1	0.0272 (19)	0.0234 (17)	0.0200 (17)	0.0102 (15)	0.0088 (14)	0.0031 (13)
N2	0.0285 (19)	0.0215 (17)	0.0191 (17)	0.0116 (15)	0.0062 (14)	0.0047 (13)
N3	0.0258 (19)	0.0246 (18)	0.0207 (17)	0.0122 (15)	0.0103 (14)	0.0084 (14)
C1	0.025 (2)	0.021 (2)	0.026 (2)	0.0067 (17)	0.0097 (18)	0.0019 (16)
C2	0.025 (2)	0.024 (2)	0.0171 (19)	0.0085 (17)	0.0100 (17)	0.0035 (16)
C3	0.0147 (19)	0.0195 (19)	0.0205 (19)	0.0066 (15)	0.0067 (16)	0.0058 (15)
C4	0.0126 (19)	0.0185 (19)	0.024 (2)	0.0037 (15)	0.0070 (16)	0.0050 (15)
C5	0.020 (2)	0.0164 (19)	0.024 (2)	0.0070 (16)	0.0057 (16)	0.0047 (15)
C6	0.018 (2)	0.020 (2)	0.025 (2)	0.0038 (16)	0.0088 (16)	0.0041 (16)
C7	0.021 (2)	0.023 (2)	0.021 (2)	0.0075 (17)	0.0077 (16)	0.0073 (16)
C8	0.024 (2)	0.0175 (19)	0.027 (2)	0.0078 (16)	0.0077 (17)	0.0071 (16)
C9	0.016 (2)	0.0194 (19)	0.024 (2)	0.0046 (16)	0.0096 (16)	0.0033 (16)
C10	0.024 (2)	0.028 (2)	0.020 (2)	0.0108 (17)	0.0086 (17)	0.0053 (16)
C11	0.018 (2)	0.0199 (19)	0.023 (2)	0.0068 (16)	0.0085 (16)	0.0071 (16)
C12	0.024 (2)	0.022 (2)	0.023 (2)	0.0102 (17)	0.0098 (17)	0.0062 (16)
C13	0.023 (2)	0.0154 (19)	0.028 (2)	0.0066 (16)	0.0109 (17)	0.0061 (16)
C14	0.022 (2)	0.023 (2)	0.022 (2)	0.0076 (17)	0.0093 (17)	0.0085 (16)
C15	0.022 (2)	0.019 (2)	0.024 (2)	0.0066 (17)	0.0041 (17)	0.0036 (16)
C16	0.024 (2)	0.0168 (19)	0.026 (2)	0.0044 (16)	0.0073 (17)	0.0093 (16)
C17	0.032 (2)	0.025 (2)	0.028 (2)	0.0113 (18)	0.0109 (18)	0.0114 (17)
O1W	0.0347 (18)	0.0205 (15)	0.0434 (18)	0.0117 (14)	0.0171 (15)	0.0123 (13)

Cl1—C7	1.740 (4)	C7—C8	1.360 (5)
O1—C14	1.377 (4)	C8—C9	1.413 (5)
O1—C17	1.435 (5)	C8—H8	0.9500
N1—C1	1.332 (5)	C10—C11	1.458 (5)
N1—C9	1.385 (5)	C10—H10	0.9500
N2—C3	1.357 (5)	C11—C12	1.385 (5)
N2—N3	1.380 (4)	C11—C16	1.409 (5)
N2—H2N	0.8800	C12—C13	1.386 (5)
N3—C10	1.274 (5)	C12—H12	0.9500
C1—C2	1.383 (5)	C13—C14	1.379 (5)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.386 (5)	C14—C15	1.400 (5)
C2—H2	0.9500	C15—C16	1.374 (5)
C3—C4	1.435 (5)	C15—H15	0.9500
C4—C9	1.417 (5)	C16—H16	0.9500
C4—C5	1.411 (5)	C17—H17A	0.9800
C5—C6	1.374 (5)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.409 (5)	O1W—H1W	0.85 (5)
C6—H6	0.9500	O1W—H2W	0.85 (5)
C14—O1—C17	117.0 (3)	N1—C9—C8	116.8 (3)
C1—N1—C9	115.5 (3)	C4—C9—C8	119.7 (3)
C3—N2—N3	119.4 (3)	N3—C10—C11	122.5 (3)
C3—N2—H2N	120.3	N3—C10—H10	118.8
N3—N2—H2N	120.3	C11—C10—H10	118.8
C10—N3—N2	115.5 (3)	C12—C11—C16	117.8 (3)
N1—C1—C2	125.9 (4)	C12—C11—C10	119.9 (3)
N1—C1—H1	117.0	C16—C11—C10	122.3 (3)
C2—C1—H1	117.0	C11—C12—C13	122.5 (4)
C1—C2—C3	119.5 (3)	C11—C12—H12	118.8
C1—C2—H2	120.3	C13—C12—H12	118.8
C3—C2—H2	120.3	C14—C13—C12	118.8 (3)
N2—C3—C2	122.1 (3)	C14—C13—H13	120.6
N2—C3—C4	120.0 (3)	C12—C13—H13	120.6
C2—C3—C4	117.9 (3)	O1—C14—C13	124.4 (3)
C9—C4—C5	118.4 (3)	O1—C14—C15	115.4 (3)
C9—C4—C3	117.7 (3)	C13—C14—C15	120.2 (3)
C5—C4—C3	123.9 (3)	C16—C15—C14	120.2 (4)
C6—C5—C4	121.3 (3)	C16—C15—H15	119.9
C6—C5—H5	119.3	C14—C15—H15	119.9
C4—C5—H5	119.3	C15—C16—C11	120.5 (3)
C5—C6—C7	119.0 (3)	C15—C16—H16	119.8
C5—C6—H6	120.5	C11—C16—H16	119.8
C7—C6—H6	120.5	O1—C17—H17A	109.5
C8—C7—C6	121.6 (3)	O1—C17—H17B	109.5
C8—C7—Cl1	120.0 (3)	H17A—C17—H17B	109.5
C6—C7—Cl1	118.3 (3)	O1—C17—H17C	109.5
C7—C8—C9	119.8 (3)	H17A—C17—H17C	109.5
C7—C8—H8	120.1	H17B—C17—H17C	109.5
C9—C8—H8	120.1	H1W—O1W—H2W	108 (5)
N1—C9—C4	123.5 (3)
C3—N2—N3—C10	172.4 (3)	C3—C4—C9—N1	2.5 (5)
C9—N1—C1—C2	−2.0 (6)	C5—C4—C9—C8	3.8 (5)
N1—C1—C2—C3	3.1 (6)	C3—C4—C9—C8	−177.0 (3)
N3—N2—C3—C2	−1.1 (5)	C7—C8—C9—N1	178.1 (3)
N3—N2—C3—C4	179.4 (3)	C7—C8—C9—C4	−2.4 (6)
C1—C2—C3—N2	179.3 (3)	N2—N3—C10—C11	179.7 (3)
C1—C2—C3—C4	−1.2 (5)	N3—C10—C11—C12	177.7 (4)
N2—C3—C4—C9	178.2 (3)	N3—C10—C11—C16	−2.8 (6)
C2—C3—C4—C9	−1.3 (5)	C16—C11—C12—C13	0.5 (6)
N2—C3—C4—C5	−2.7 (5)	C10—C11—C12—C13	180.0 (4)
C2—C3—C4—C5	177.8 (3)	C11—C12—C13—C14	0.3 (6)
C9—C4—C5—C6	−1.8 (5)	C17—O1—C14—C13	−2.2 (5)
C3—C4—C5—C6	179.1 (4)	C17—O1—C14—C15	178.0 (3)
C4—C5—C6—C7	−1.6 (6)	C12—C13—C14—O1	179.4 (4)
C5—C6—C7—C8	3.1 (6)	C12—C13—C14—C15	−0.9 (6)
C5—C6—C7—Cl1	−176.5 (3)	O1—C14—C15—C16	−179.5 (3)
C6—C7—C8—C9	−1.1 (6)	C13—C14—C15—C16	0.7 (6)
Cl1—C7—C8—C9	178.5 (3)	C14—C15—C16—C11	0.1 (6)
C1—N1—C9—C4	−0.9 (5)	C12—C11—C16—C15	−0.7 (6)
C1—N1—C9—C8	178.6 (3)	C10—C11—C16—C15	179.8 (4)
C5—C4—C9—N1	−176.7 (3)

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···N1i	0.85 (5)	2.02 (5)	2.867 (4)	172 (5)
N2—H2n···O1wii	0.88	2.18	3.007 (4)	157
O1w—H2w···N1	0.85 (5)	2.20 (5)	3.047 (5)	175 (5)
C5—H5···O1wii	0.95	2.45	3.380 (5)	165
C17—H17a···Cgiii	0.98	2.65	3.508 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯N1i	0.85 (5)	2.02 (5)	2.867 (4)	172 (5)
O1w—H2w⋯N1	0.85 (5)	2.20 (5)	3.047 (5)	175 (5)
N2—H2n⋯O1wii	0.88	2.18	3.007 (4)	157
C5—H5⋯O1wii	0.95	2.45	3.380 (5)	165
C17—H17a⋯Cgiii	0.98	2.65	3.508 (5)	147

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