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

In the title hydrate, C(17)H(14)ClN(3)O·H(2)O, the dihedral angle between the quinoline fused-ring system and the benzene ring is 13.4 (2)° and the conformation about the C=N bond is E. In the crystal, N(h)-H⋯O(w) and O(w)-H⋯N(q) (h = hydro-zone, w = water and q = quinoline) hydrogen bonds generate a two-dimenstional network in the ac plane. A weak C-H⋯O inter-action helps to consolidate the packing.

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 ▶). For the structure of the isomeric 2-meth­oxy structure, see: de Lima Ferreira et al. (2010 ▶).

Experimental

Crystal data

C17H14ClN3O·H2O

M = 329.78

Monoclinic,

a = 3.9202 (2) Å

b = 24.5084 (17) Å

c = 16.1212 (11) Å

β = 91.639 (4)°

V = 1548.26 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.62 × 0.03 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.735, T max = 0.995

11507 measured reflections

2716 independent reflections

1769 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.093

wR(F 2) = 0.260

S = 1.04

2716 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.45 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: 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/S1600536810006586/hb5340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006586/hb5340Isup2.hkl

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

C17H14ClN3O·H2O	F(000) = 688
Mr = 329.78	Dx = 1.415 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9260 reflections
a = 3.9202 (2) Å	θ = 2.9–27.5°
b = 24.5084 (17) Å	µ = 0.26 mm−1
c = 16.1212 (11) Å	T = 120 K
β = 91.639 (4)°	Needle, colourless
V = 1548.26 (17) Å3	0.62 × 0.03 × 0.02 mm
Z = 4

Nonius KappaCCD diffractometer	2716 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1769 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.096
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −29→29
Tmin = 0.735, Tmax = 0.995	l = −19→19
11507 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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.260	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.1P)2 + 10.4045P] where P = (Fo2 + 2Fc2)/3
2716 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.45 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	0.0208 (4)	0.57108 (6)	0.05313 (10)	0.0256 (5)
O1	1.3298 (11)	0.93299 (18)	0.2940 (3)	0.0232 (10)
N1	0.1966 (13)	0.7497 (2)	−0.0985 (3)	0.0201 (12)
N2	0.6619 (13)	0.8261 (2)	0.1080 (3)	0.0214 (12)
H2N	0.6968	0.8080	0.1547	0.026*
N3	0.7680 (12)	0.8795 (2)	0.1015 (3)	0.0195 (12)
C1	0.2920 (16)	0.8018 (3)	−0.0989 (4)	0.0232 (15)
H1	0.2504	0.8220	−0.1484	0.028*
C2	0.4479 (15)	0.8288 (2)	−0.0322 (4)	0.0183 (13)
H2	0.5157	0.8658	−0.0377	0.022*
C3	0.5046 (15)	0.8016 (2)	0.0426 (4)	0.0203 (14)
C4	0.3926 (15)	0.7459 (2)	0.0470 (4)	0.0176 (13)
C5	0.4234 (15)	0.7141 (3)	0.1204 (4)	0.0223 (14)
H5	0.5240	0.7296	0.1692	0.027*
C6	0.3094 (16)	0.6611 (2)	0.1217 (4)	0.0206 (14)
H6	0.3293	0.6402	0.1712	0.025*
C7	0.1640 (15)	0.6384 (2)	0.0496 (4)	0.0176 (13)
C8	0.1307 (16)	0.6672 (3)	−0.0225 (4)	0.0213 (14)
H8	0.0329	0.6504	−0.0707	0.026*
C9	0.2419 (15)	0.7222 (2)	−0.0257 (4)	0.0180 (13)
C10	0.9303 (15)	0.8980 (3)	0.1657 (4)	0.0211 (14)
H10	0.9774	0.8745	0.2115	0.025*
C11	1.0442 (14)	0.9551 (2)	0.1693 (4)	0.0164 (13)
C12	1.2380 (14)	0.9726 (2)	0.2387 (4)	0.0181 (14)
C13	1.3295 (16)	1.0271 (3)	0.2466 (4)	0.0237 (15)
H13	1.4596	1.0391	0.2938	0.028*
C14	1.2299 (16)	1.0641 (3)	0.1851 (4)	0.0222 (14)
H14	1.2908	1.1014	0.1909	0.027*
C15	1.0422 (16)	1.0471 (3)	0.1152 (4)	0.0249 (15)
H15	0.9778	1.0725	0.0731	0.030*
C16	0.9495 (15)	0.9922 (2)	0.1078 (4)	0.0212 (14)
H16	0.8211	0.9802	0.0604	0.025*
C17	1.5235 (16)	0.9495 (3)	0.3666 (4)	0.0242 (15)
H17A	1.7439	0.9642	0.3501	0.036*
H17B	1.5613	0.9179	0.4030	0.036*
H17C	1.3976	0.9777	0.3962	0.036*
O1W	0.7223 (14)	0.7893 (2)	0.2807 (3)	0.0304 (12)
H1W	0.53 (2)	0.785 (3)	0.300 (5)	0.046*
H2W	0.89 (2)	0.780 (3)	0.309 (5)	0.046*

	U11	U22	U33	U12	U13	U23
Cl1	0.0319 (9)	0.0186 (8)	0.0263 (9)	−0.0044 (7)	−0.0002 (7)	0.0044 (7)
O1	0.028 (2)	0.023 (2)	0.018 (2)	0.0005 (19)	−0.0047 (18)	−0.001 (2)
N1	0.027 (3)	0.019 (3)	0.015 (3)	−0.002 (2)	−0.003 (2)	0.002 (2)
N2	0.027 (3)	0.020 (3)	0.017 (3)	−0.002 (2)	−0.003 (2)	0.002 (2)
N3	0.022 (3)	0.015 (3)	0.022 (3)	−0.002 (2)	0.004 (2)	−0.002 (2)
C1	0.026 (3)	0.026 (4)	0.017 (4)	0.000 (3)	−0.005 (3)	0.008 (3)
C2	0.023 (3)	0.015 (3)	0.017 (3)	−0.001 (2)	0.004 (3)	−0.004 (3)
C3	0.018 (3)	0.020 (3)	0.022 (4)	0.002 (3)	−0.003 (3)	−0.004 (3)
C4	0.016 (3)	0.020 (3)	0.017 (3)	0.001 (2)	0.005 (2)	0.001 (3)
C5	0.023 (3)	0.025 (3)	0.019 (4)	0.002 (3)	−0.002 (3)	0.000 (3)
C6	0.029 (3)	0.015 (3)	0.018 (4)	0.002 (3)	0.001 (3)	−0.001 (3)
C7	0.019 (3)	0.017 (3)	0.018 (3)	0.002 (2)	0.008 (2)	−0.002 (3)
C8	0.023 (3)	0.024 (3)	0.017 (4)	−0.004 (3)	−0.004 (3)	−0.001 (3)
C9	0.023 (3)	0.016 (3)	0.015 (3)	0.000 (2)	−0.002 (3)	−0.002 (3)
C10	0.019 (3)	0.021 (3)	0.023 (4)	0.001 (3)	0.002 (3)	0.005 (3)
C11	0.014 (3)	0.016 (3)	0.018 (3)	−0.004 (2)	0.001 (2)	−0.003 (3)
C12	0.014 (3)	0.019 (3)	0.022 (4)	0.001 (2)	0.006 (2)	−0.004 (3)
C13	0.027 (3)	0.026 (3)	0.018 (4)	−0.001 (3)	0.000 (3)	0.001 (3)
C14	0.026 (3)	0.015 (3)	0.026 (4)	−0.007 (3)	0.011 (3)	−0.003 (3)
C15	0.027 (3)	0.019 (3)	0.029 (4)	0.006 (3)	0.003 (3)	0.003 (3)
C16	0.024 (3)	0.018 (3)	0.021 (4)	0.001 (3)	0.004 (3)	−0.004 (3)
C17	0.022 (3)	0.030 (4)	0.021 (4)	−0.002 (3)	−0.002 (3)	−0.005 (3)
O1W	0.028 (3)	0.039 (3)	0.024 (3)	0.000 (2)	−0.005 (2)	0.004 (2)

Cl1—C7	1.744 (6)	C7—C8	1.362 (9)
O1—C12	1.360 (7)	C8—C9	1.419 (9)
O1—C17	1.434 (7)	C8—H8	0.9500
N1—C1	1.330 (8)	C10—C11	1.471 (8)
N1—C9	1.361 (8)	C10—H10	0.9500
N2—C3	1.348 (8)	C11—C16	1.388 (9)
N2—N3	1.379 (7)	C11—C12	1.401 (8)
N2—H2N	0.8800	C12—C13	1.388 (9)
N3—C10	1.282 (8)	C13—C14	1.391 (9)
C1—C2	1.389 (9)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.391 (9)
C2—C3	1.391 (9)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.399 (9)
C3—C4	1.436 (8)	C15—H15	0.9500
C4—C9	1.420 (8)	C16—H16	0.9500
C4—C5	1.420 (9)	C17—H17A	0.9800
C5—C6	1.372 (9)	C17—H17B	0.9800
C5—H5	0.9500	C17—H17C	0.9800
C6—C7	1.396 (9)	O1W—H1W	0.81 (9)
C6—H6	0.9500	O1W—H2W	0.82 (9)
C12—O1—C17	117.2 (5)	N1—C9—C4	123.4 (5)
C1—N1—C9	116.6 (5)	C8—C9—C4	118.6 (6)
C3—N2—N3	119.7 (5)	N3—C10—C11	120.7 (6)
C3—N2—H2N	120.2	N3—C10—H10	119.6
N3—N2—H2N	120.2	C11—C10—H10	119.6
C10—N3—N2	114.6 (5)	C16—C11—C12	119.9 (6)
N1—C1—C2	124.9 (6)	C16—C11—C10	121.4 (5)
N1—C1—H1	117.6	C12—C11—C10	118.7 (5)
C2—C1—H1	117.6	O1—C12—C13	124.3 (6)
C1—C2—C3	119.9 (6)	O1—C12—C11	115.7 (5)
C1—C2—H2	120.1	C13—C12—C11	120.0 (6)
C3—C2—H2	120.1	C12—C13—C14	119.6 (6)
N2—C3—C2	121.6 (6)	C12—C13—H13	120.2
N2—C3—C4	121.2 (6)	C14—C13—H13	120.2
C2—C3—C4	117.2 (5)	C15—C14—C13	120.9 (6)
C9—C4—C5	119.1 (5)	C15—C14—H14	119.5
C9—C4—C3	117.9 (5)	C13—C14—H14	119.5
C5—C4—C3	122.9 (6)	C14—C15—C16	119.1 (6)
C6—C5—C4	120.8 (6)	C14—C15—H15	120.4
C6—C5—H5	119.6	C16—C15—H15	120.4
C4—C5—H5	119.6	C11—C16—C15	120.3 (6)
C5—C6—C7	119.3 (6)	C11—C16—H16	119.8
C5—C6—H6	120.3	C15—C16—H16	119.8
C7—C6—H6	120.3	O1—C17—H17A	109.5
C8—C7—C6	122.0 (6)	O1—C17—H17B	109.5
C8—C7—Cl1	119.7 (5)	H17A—C17—H17B	109.5
C6—C7—Cl1	118.3 (5)	O1—C17—H17C	109.5
C7—C8—C9	120.1 (6)	H17A—C17—H17C	109.5
C7—C8—H8	119.9	H17B—C17—H17C	109.5
C9—C8—H8	119.9	H1W—O1W—H2W	118 (9)
N1—C9—C8	118.0 (5)
C3—N2—N3—C10	−176.6 (6)	C7—C8—C9—C4	1.1 (9)
C9—N1—C1—C2	3.4 (9)	C5—C4—C9—N1	178.9 (6)
N1—C1—C2—C3	−2.1 (10)	C3—C4—C9—N1	−0.4 (9)
N3—N2—C3—C2	0.5 (9)	C5—C4—C9—C8	−0.8 (9)
N3—N2—C3—C4	179.6 (5)	C3—C4—C9—C8	179.9 (6)
C1—C2—C3—N2	178.5 (6)	N2—N3—C10—C11	−177.0 (5)
C1—C2—C3—C4	−0.6 (9)	N3—C10—C11—C16	6.9 (9)
N2—C3—C4—C9	−177.4 (6)	N3—C10—C11—C12	−176.3 (6)
C2—C3—C4—C9	1.7 (8)	C17—O1—C12—C13	2.3 (9)
N2—C3—C4—C5	3.3 (9)	C17—O1—C12—C11	−178.9 (5)
C2—C3—C4—C5	−177.6 (6)	C16—C11—C12—O1	−177.5 (5)
C9—C4—C5—C6	0.0 (9)	C10—C11—C12—O1	5.6 (8)
C3—C4—C5—C6	179.3 (6)	C16—C11—C12—C13	1.3 (9)
C4—C5—C6—C7	0.5 (9)	C10—C11—C12—C13	−175.6 (6)
C5—C6—C7—C8	−0.1 (9)	O1—C12—C13—C14	178.2 (6)
C5—C6—C7—Cl1	−179.9 (5)	C11—C12—C13—C14	−0.5 (9)
C6—C7—C8—C9	−0.7 (10)	C12—C13—C14—C15	−0.6 (10)
Cl1—C7—C8—C9	179.1 (5)	C13—C14—C15—C16	0.9 (10)
C1—N1—C9—C8	177.7 (6)	C12—C11—C16—C15	−1.0 (9)
C1—N1—C9—C4	−2.0 (9)	C10—C11—C16—C15	175.8 (6)
C7—C8—C9—N1	−178.6 (6)	C14—C15—C16—C11	−0.1 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1W	0.88	2.08	2.928 (7)	161
O1W—H1W···N1i	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W···N1ii	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5···O1W	0.95	2.43	3.358 (8)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1W	0.88	2.08	2.928 (7)	161
O1W—H1W⋯N1i	0.81 (9)	2.30 (9)	3.030 (8)	150 (8)
O1W—H2W⋯N1ii	0.82 (9)	2.03 (9)	2.820 (7)	163 (8)
C5—H5⋯O1W	0.95	2.43	3.358 (8)	166

Symmetry codes: (i) ; (ii) .