4-[(E)-2-(2,4-Dichloro-benzyl-idene)hydrazin-1-yl]quinolin-1-ium chloride monohydrate.

In the title hydrated salt, C(16)H(12)Cl(2)N(3) (+)·Cl(-)·H(2)O, there is a small twist in the cation as seen in the torsion angle linking the benzene ring to the rest of the mol-ecule [171.96 (17)°]. In the crystal, the quinolinium H atom forms a hydrogen bond to the lattice water mol-ecule, which also forms hydrogen bonds to two Cl(-) anions. Each Cl(-) ion also accepts a hydrogen bond from the hydrazine H atom. The three-dimensional architecture is also stabilized by π-π inter-actions between centrosymmetrically related quinoline residues [centroid-centroid distance = 3.5574 (11) Å].

Related literature

For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009 ▶), Candea et al. (2009 ▶); Montenegro et al. (2011 ▶, 2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶).

Experimental

Crystal data

C16H12Cl2N3 +·Cl−·H2O

M = 370.65

Triclinic,

a = 7.6815 (2) Å

b = 9.7491 (3) Å

c = 10.8418 (3) Å

α = 87.831 (2)°

β = 87.171 (2)°

γ = 87.146 (2)°

V = 809.41 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 120 K

0.10 × 0.09 × 0.08 mm

Data collection

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.666, T max = 0.746

16815 measured reflections

3701 independent reflections

3016 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.06

3701 reflections

220 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.34 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 datablock(s) global, I. DOI: 10.1107/S1600536812012962/xu5495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012962/xu5495Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012962/xu5495Isup3.cml

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

C16H12Cl2N3+·Cl−·H2O	Z = 2
Mr = 370.65	F(000) = 380
Triclinic, P1	Dx = 1.521 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6815 (2) Å	Cell parameters from 10943 reflections
b = 9.7491 (3) Å	θ = 2.9–27.5°
c = 10.8418 (3) Å	µ = 0.57 mm−1
α = 87.831 (2)°	T = 120 K
β = 87.171 (2)°	Block, colourless
γ = 87.146 (2)°	0.10 × 0.09 × 0.08 mm
V = 809.41 (4) Å3

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	3701 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	3016 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→12
Tmin = 0.666, Tmax = 0.746	l = −14→14
16815 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.2111P] where P = (Fo2 + 2Fc2)/3
3701 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.36 e Å−3
5 restraints	Δρmin = −0.34 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	0.23598 (6)	1.20701 (5)	0.14241 (5)	0.02343 (14)
Cl2	0.81838 (6)	1.41676 (5)	−0.06262 (5)	0.02564 (14)
N1	0.7250 (2)	0.35248 (17)	0.32132 (15)	0.0184 (3)
H1n	0.785 (2)	0.2747 (14)	0.337 (2)	0.022*
N2	0.4580 (2)	0.72610 (16)	0.26643 (15)	0.0176 (3)
H2n	0.3464 (14)	0.740 (2)	0.2871 (19)	0.021*
N3	0.5488 (2)	0.83194 (16)	0.21124 (14)	0.0177 (3)
C1	0.8043 (3)	0.4576 (2)	0.26455 (18)	0.0207 (4)
H1	0.9235	0.4453	0.2378	0.025*
C2	0.7194 (2)	0.5834 (2)	0.24339 (17)	0.0196 (4)
H2	0.7794	0.6566	0.2029	0.024*
C3	0.5435 (2)	0.60214 (19)	0.28223 (16)	0.0161 (4)
C4	0.4548 (2)	0.48914 (19)	0.34195 (16)	0.0157 (4)
C5	0.2776 (2)	0.4957 (2)	0.38498 (17)	0.0186 (4)
H5	0.2080	0.5778	0.3719	0.022*
C6	0.2056 (3)	0.3845 (2)	0.44529 (18)	0.0207 (4)
H6	0.0868	0.3907	0.4742	0.025*
C7	0.3057 (3)	0.2609 (2)	0.46494 (18)	0.0218 (4)
H7	0.2544	0.1849	0.5074	0.026*
C8	0.4769 (3)	0.2506 (2)	0.42284 (18)	0.0202 (4)
H8	0.5441	0.1672	0.4353	0.024*
C9	0.5527 (2)	0.36373 (19)	0.36120 (16)	0.0167 (4)
C10	0.4620 (2)	0.94746 (19)	0.19875 (17)	0.0176 (4)
H10	0.3440	0.9576	0.2288	0.021*
C11	0.5500 (2)	1.06322 (19)	0.13685 (17)	0.0171 (4)
C12	0.4584 (2)	1.18619 (19)	0.10639 (17)	0.0174 (4)
C13	0.5395 (2)	1.2951 (2)	0.04510 (17)	0.0190 (4)
H13	0.4754	1.3783	0.0258	0.023*
C14	0.7152 (3)	1.27973 (19)	0.01280 (17)	0.0193 (4)
C15	0.8113 (2)	1.1589 (2)	0.04001 (18)	0.0210 (4)
H15	0.9317	1.1491	0.0157	0.025*
C16	0.7286 (3)	1.0533 (2)	0.10297 (18)	0.0207 (4)
H16	0.7945	0.9715	0.1241	0.025*
Cl3	0.05983 (6)	0.83146 (5)	0.32453 (5)	0.02497 (14)
O1w	0.8874 (3)	0.11709 (18)	0.39542 (16)	0.0445 (5)
H1w	0.908 (4)	0.119 (3)	0.4704 (12)	0.067*
H2w	0.933 (4)	0.0432 (19)	0.370 (3)	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0168 (2)	0.0208 (3)	0.0321 (3)	0.00144 (18)	0.00122 (19)	0.0017 (2)
Cl2	0.0283 (3)	0.0229 (3)	0.0258 (3)	−0.0093 (2)	0.0037 (2)	0.0014 (2)
N1	0.0188 (8)	0.0192 (8)	0.0164 (8)	0.0052 (7)	0.0006 (6)	0.0008 (7)
N2	0.0171 (8)	0.0150 (8)	0.0206 (8)	0.0000 (6)	−0.0001 (6)	0.0007 (6)
N3	0.0196 (8)	0.0164 (8)	0.0173 (8)	−0.0033 (6)	−0.0013 (6)	0.0015 (6)
C1	0.0190 (9)	0.0238 (10)	0.0187 (10)	0.0020 (8)	0.0007 (8)	0.0009 (8)
C2	0.0209 (9)	0.0189 (10)	0.0187 (10)	−0.0016 (8)	0.0001 (8)	0.0026 (8)
C3	0.0198 (9)	0.0174 (9)	0.0112 (8)	0.0004 (7)	−0.0021 (7)	−0.0019 (7)
C4	0.0186 (9)	0.0162 (9)	0.0125 (9)	0.0005 (7)	−0.0026 (7)	−0.0007 (7)
C5	0.0201 (9)	0.0176 (10)	0.0177 (9)	0.0032 (8)	−0.0018 (8)	−0.0009 (7)
C6	0.0208 (10)	0.0207 (10)	0.0205 (10)	−0.0015 (8)	0.0008 (8)	−0.0019 (8)
C7	0.0257 (10)	0.0189 (10)	0.0204 (10)	−0.0030 (8)	0.0020 (8)	0.0022 (8)
C8	0.0270 (10)	0.0154 (9)	0.0180 (10)	0.0022 (8)	−0.0031 (8)	0.0011 (7)
C9	0.0190 (9)	0.0179 (10)	0.0131 (9)	0.0020 (8)	−0.0017 (7)	−0.0022 (7)
C10	0.0176 (9)	0.0182 (10)	0.0169 (9)	−0.0005 (8)	−0.0001 (7)	−0.0003 (7)
C11	0.0187 (9)	0.0180 (10)	0.0150 (9)	−0.0025 (7)	−0.0009 (7)	−0.0021 (7)
C12	0.0163 (9)	0.0187 (10)	0.0175 (9)	−0.0004 (7)	−0.0019 (7)	−0.0034 (7)
C13	0.0229 (10)	0.0162 (9)	0.0179 (10)	−0.0009 (8)	−0.0013 (8)	0.0010 (7)
C14	0.0247 (10)	0.0169 (10)	0.0172 (9)	−0.0078 (8)	−0.0023 (8)	−0.0005 (7)
C15	0.0173 (9)	0.0230 (10)	0.0229 (10)	−0.0020 (8)	0.0008 (8)	−0.0031 (8)
C16	0.0210 (10)	0.0186 (10)	0.0225 (10)	0.0020 (8)	−0.0024 (8)	−0.0016 (8)
Cl3	0.0219 (3)	0.0205 (3)	0.0312 (3)	0.00329 (19)	0.0060 (2)	0.0001 (2)
O1w	0.0646 (12)	0.0317 (9)	0.0356 (10)	0.0289 (9)	−0.0141 (9)	−0.0066 (8)

Cl1—C12	1.7374 (19)	C6—H6	0.9500
Cl2—C14	1.7435 (19)	C7—C8	1.371 (3)
N1—C1	1.334 (3)	C7—H7	0.9500
N1—C9	1.372 (2)	C8—C9	1.404 (3)
N1—H1n	0.884 (9)	C8—H8	0.9500
N2—C3	1.355 (2)	C10—C11	1.468 (3)
N2—N3	1.376 (2)	C10—H10	0.9500
N2—H2n	0.881 (9)	C11—C12	1.396 (3)
N3—C10	1.286 (2)	C11—C16	1.402 (3)
C1—C2	1.377 (3)	C12—C13	1.388 (3)
C1—H1	0.9500	C13—C14	1.380 (3)
C2—C3	1.401 (3)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.389 (3)
C3—C4	1.440 (3)	C15—C16	1.377 (3)
C4—C9	1.418 (2)	C15—H15	0.9500
C4—C5	1.416 (3)	C16—H16	0.9500
C5—C6	1.371 (3)	O1w—H1w	0.836 (10)
C5—H5	0.9500	O1w—H2w	0.834 (10)
C6—C7	1.412 (3)
C1—N1—C9	121.52 (16)	C7—C8—C9	119.77 (17)
C1—N1—H1n	119.8 (14)	C7—C8—H8	120.1
C9—N1—H1n	118.6 (14)	C9—C8—H8	120.1
C3—N2—N3	118.12 (16)	N1—C9—C8	119.09 (16)
C3—N2—H2n	122.5 (14)	N1—C9—C4	119.98 (17)
N3—N2—H2n	119.3 (14)	C8—C9—C4	120.93 (17)
C10—N3—N2	115.69 (16)	N3—C10—C11	118.31 (17)
N1—C1—C2	122.28 (18)	N3—C10—H10	120.8
N1—C1—H1	118.9	C11—C10—H10	120.8
C2—C1—H1	118.9	C12—C11—C16	117.33 (17)
C1—C2—C3	119.17 (18)	C12—C11—C10	121.41 (17)
C1—C2—H2	120.4	C16—C11—C10	121.24 (17)
C3—C2—H2	120.4	C13—C12—C11	121.87 (17)
N2—C3—C2	120.53 (17)	C13—C12—Cl1	117.49 (14)
N2—C3—C4	120.06 (17)	C11—C12—Cl1	120.64 (15)
C2—C3—C4	119.39 (17)	C14—C13—C12	118.55 (18)
C9—C4—C5	117.85 (17)	C14—C13—H13	120.7
C9—C4—C3	117.65 (17)	C12—C13—H13	120.7
C5—C4—C3	124.49 (17)	C13—C14—C15	121.63 (18)
C6—C5—C4	120.52 (17)	C13—C14—Cl2	118.79 (15)
C6—C5—H5	119.7	C15—C14—Cl2	119.58 (15)
C4—C5—H5	119.7	C16—C15—C14	118.69 (18)
C5—C6—C7	120.85 (18)	C16—C15—H15	120.7
C5—C6—H6	119.6	C14—C15—H15	120.7
C7—C6—H6	119.6	C15—C16—C11	121.90 (18)
C8—C7—C6	120.07 (18)	C15—C16—H16	119.0
C8—C7—H7	120.0	C11—C16—H16	119.0
C6—C7—H7	120.0	H1w—O1w—H2w	107 (3)
C3—N2—N3—C10	−179.79 (16)	C5—C4—C9—N1	−179.89 (16)
C9—N1—C1—C2	0.5 (3)	C3—C4—C9—N1	−1.2 (3)
N1—C1—C2—C3	−0.2 (3)	C5—C4—C9—C8	−1.1 (3)
N3—N2—C3—C2	0.1 (3)	C3—C4—C9—C8	177.65 (16)
N3—N2—C3—C4	178.67 (15)	N2—N3—C10—C11	−178.02 (15)
C1—C2—C3—N2	177.78 (17)	N3—C10—C11—C12	171.96 (17)
C1—C2—C3—C4	−0.8 (3)	N3—C10—C11—C16	−6.3 (3)
N2—C3—C4—C9	−177.12 (16)	C16—C11—C12—C13	0.0 (3)
C2—C3—C4—C9	1.5 (3)	C10—C11—C12—C13	−178.37 (17)
N2—C3—C4—C5	1.5 (3)	C16—C11—C12—Cl1	178.98 (14)
C2—C3—C4—C5	−179.93 (17)	C10—C11—C12—Cl1	0.6 (3)
C9—C4—C5—C6	1.2 (3)	C11—C12—C13—C14	0.6 (3)
C3—C4—C5—C6	−177.37 (17)	Cl1—C12—C13—C14	−178.43 (14)
C4—C5—C6—C7	−0.5 (3)	C12—C13—C14—C15	0.1 (3)
C5—C6—C7—C8	−0.4 (3)	C12—C13—C14—Cl2	−179.28 (14)
C6—C7—C8—C9	0.6 (3)	C13—C14—C15—C16	−1.3 (3)
C1—N1—C9—C8	−178.63 (17)	Cl2—C14—C15—C16	178.04 (15)
C1—N1—C9—C4	0.2 (3)	C14—C15—C16—C11	1.9 (3)
C7—C8—C9—N1	178.98 (17)	C12—C11—C16—C15	−1.3 (3)
C7—C8—C9—C4	0.1 (3)	C10—C11—C16—C15	177.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1w	0.88 (2)	1.80 (2)	2.673 (2)	170 (2)
O1w—H1w···Cl3i	0.84 (2)	2.32 (2)	3.1451 (18)	169 (3)
N2—H2n···Cl3	0.88 (1)	2.36 (1)	3.2175 (16)	166 (2)
O1w—H2w···Cl3ii	0.84 (2)	2.30 (2)	3.1295 (19)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1w	0.88 (2)	1.80 (2)	2.673 (2)	170 (2)
O1w—H1w⋯Cl3i	0.84 (2)	2.32 (2)	3.1451 (18)	169 (3)
N2—H2n⋯Cl3	0.88 (1)	2.36 (1)	3.2175 (16)	166 (2)
O1w—H2w⋯Cl3ii	0.84 (2)	2.30 (2)	3.1295 (19)	173 (3)

Symmetry codes: (i) ; (ii) .