4-[(E)-2-(2-Chloro­benzyl­idene)hydrazin-1-yl]quinolin-1-ium chloride dihydrate

Tiekink, E.R.T.; Wardell, S.M.S.V.; Wardell, J.L.; Ferreira, M. de L.; Souza, M.V.N. de; Kaiser, C.R.

doi:10.1107/S1600536812022660

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1850-o1851

doi:10.1107/S1600536812022660

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4-[(E)-2-(2-Chlorobenzylidene)hydrazin-1-yl]quinolin-1-ium chloride dihydrate

Edward R. T. Tiekink,^a ^* Solange M. S. V. Wardell,^b James L. Wardell,^c ‡ Marcelle de Lima Ferreira,^d Marcus V. N. de Souza ^d and Carlos R. Kaiser ^e

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^bCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, ^cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, ^dInstituto de Tecnologia em Fármacos–Farmanguinhos, FioCruz–Fundação, Oswaldo Cruz, R. Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, and ^ePrograma de Pós-Graduaçõ em Química, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, Brazil
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 9 May 2012; accepted 18 May 2012; online 23 May 2012)

In the title hydrated salt, C₁₆H₁₃ClN₃⁺·Cl⁻·2H₂O, a small twist is evident in the cation so that the chlorobenzene ring is not coplanar with the central hydrazinyl group [the N—C—C—C torsion angle = −4.8 (12)°]. The conformation about the imine N=C bond [1.284 (10) Å] is E. The components of the structure are connected into a three-dimensional architecture via O—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonds. One water H atom is disposed over two sites of equal occupancy.

Related literature

For the biological activity, including the 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 , 2012 ); Ferreira et al. (2012 ); Wardell et al. (2012 ).

Experimental

Crystal data

C₁₆H₁₃ClN₃⁺·Cl⁻·2H₂O
M_r = 354.23
Monoclinic, P 2₁ /c
a = 4.5946 (3) Å
b = 20.1550 (19) Å
c = 18.2192 (17) Å
β = 96.660 (5)°
V = 1675.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 120 K
0.33 × 0.02 × 0.01 mm

Data collection

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.786, T_max = 1.000
14027 measured reflections
2924 independent reflections
1565 reflections with I > 2σ(I)
R_int = 0.146

Refinement

R[F² > 2σ(F²)] = 0.096
wR(F²) = 0.223
S = 1.06
2924 reflections
229 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯Cl2	0.88 (5)	2.32 (5)	3.192 (7)	173 (6)
O1w—H1w⋯Cl2	0.84 (6)	2.37 (6)	3.207 (7)	177 (11)
N2—H2n⋯Cl2ⁱ	0.88 (6)	2.49 (6)	3.349 (7)	166 (7)
O1w—H2w⋯Cl2ⁱⁱ	0.84 (5)	2.42 (7)	3.192 (7)	154 (8)
O2w—H3w⋯O1wⁱⁱⁱ	0.84 (7)	1.96 (7)	2.801 (9)	174 (10)
O2w—H4w⋯O2w^iv	0.84 (8)	2.08 (10)	2.804 (10)	144 (11)
O2w—H5w⋯O2wⁱⁱⁱ	0.83 (12)	2.05 (13)	2.804 (10)	151 (10)
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812022660/kj2202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022660/kj2202Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022660/kj2202Isup3.cml

checkCIF report

Comment top

A wide range of pharmacological activities have been noted for compounds containing the quinoline nucleus (de Souza et al., 2009), including anti-tubercular (Candea et al., 2009) and anti-tumour (Montenegro et al., 2012) activities. Recently, we have focused attention on arylaldehyde 7-chloroquinoline-4-hydrazone derivatives (Candea et al., 2009; Montenegro et al., 2011). Complementing synthetic studies are crystallographic investigations of these hydrazones (Howie et al., 2010; de Souza et al., 2010; Ferreira et al., 2012; de Souza et al., 2012). We have recently turned our attention to arylaldehyde quinoline-4-hydrazone derivatives (Wardell et al., 2012) and now wish to report the crystal structure of the title hydrated salt, (I).

The asymmetric unit of (I), Fig. 1, comprises a 4-[(E)-2-[(2-Chlorophenyl)methylidene]hydrazin-1-yl]quinolin-1-ium cation, a chloride anion and two lattice water molecules. The quinolinyl residue is co-planar with the central hydrazinyl group [the N3—N2—C3—C2 torsional angle is -1.3 (11)°], but the chlorobenzene ring is slightly twisted out of this plane [N3—C10—C11—C16 = -4.8 (12)°]. The conformation about the N3═C10 bond [1.284 (10) Å] is E. The molecular structure of (I) resembles very closely that of the 2,4-dichloro analogue (Wardell et al., 2012).

The crystal packing in (I) is dominated by hydrogen bonding interactions, Table 1. The water molecules aggregate into chains along the a axis, Fig. 2. One of the O2w—H atoms forms a hydrogen bond to the O1w—O atom. The remaining H atom on O2w is disordered over two positions of equal weight. These interact with adjacent O2w-water molecules as shown in Fig. 2. The two H atoms of O1w form hydrogen bonds with translationally related Cl anions, Fig. 2. Finally, each Cl anion is connected in turn to two quinolinium-H atoms to connect the components of (I) into a three-dimensional architecture, Fig. 3.

Related literature top

For the biological activity, including the 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, 2012); Ferreira et al. (2012); Wardell et al. (2012).

Experimental top

A solution of 4-hydrazinoquinoline hydrochloride 1 (1.03 mmol) and 2-chlorobenzaldehyde 2 (1.24 mmol) in ethanol (5 ml) was stirred for 8 h at room temperature and then rotary evaporated. The solid residue was washed with cold Et₂O (3 \x 10 ml), and recrystallized from EtOH to give the title salt as a dihydrate; M.pt 554–555 K. ¹H NMR (400 MHz, DMSO-d₆) δ: 14.38 (ls, 1H, NH), 13.07 (ls, 1H, NH), 9.29 (s, 1H, H3'), 8.87 (d, J = 8.4 Hz, 1H, H5), 8.72 (d, J = 6.8 Hz, 1H, H2), (t, J = 7.7 Hz, 1H, H7'), 8.11 (d, J = 8.4 Hz, 1H, H8), 8.04 (t, J = 8.4 Hz, 1H, H7), 7.83 (t, J = 8.4 Hz, 1H, H6), 7.71 (d, J = 6.8 Hz, 1H, H3), 7.60 (d, J = 7.3 Hz, 1H, H8'), 7.57 – 7.47 (m, 2H, H6' and H9').

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top

	Fig. 1. The molecular structure showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only one position of the disordered H atoms of the O2w water molecule is shown.
	Fig. 2. Detail of the hydrogen bonding along the a axis in (I). The O—H···O, O—H···Cl and N—H···Cl hydrogen bonds are shown as orange, green and blue dashed lines, respectively. Only the chloride anions, water molecules and N-bound H atoms are illustrated. The water molecule was disordered with sites of equal weight being resolved for one water-H atom (see text).
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The O—H···O, O—H···Cl and N—H···Cl hydrogen bonds are shown as orange, green and blue dashed lines, respectively.

4-[(E)-2-(2-Chlorobenzylidene)hydrazin-1-yl]quinolin-1-ium chloride dihydrate top

Crystal data top

C₁₆H₁₃ClN₃⁺·Cl⁻·2H₂O	F(000) = 736
M_r = 354.23	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20901 reflections
a = 4.5946 (3) Å	θ = 2.9–27.5°
b = 20.1550 (19) Å	µ = 0.40 mm⁻¹
c = 18.2192 (17) Å	T = 120 K
β = 96.660 (5)°	Needle, colourless
V = 1675.8 (2) Å³	0.33 × 0.02 × 0.01 mm
Z = 4

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	2924 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1565 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.146
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ϕ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −23→23
T_min = 0.786, T_max = 1.000	l = −21→21
14027 measured reflections

Refinement top

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)] = 0.096	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.P)² + 18.2957P] where P = (F_o² + 2F_c²)/3
2924 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.46 e Å⁻³
11 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₃⁺·Cl⁻·2H₂O	V = 1675.8 (2) Å³
M_r = 354.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.5946 (3) Å	µ = 0.40 mm⁻¹
b = 20.1550 (19) Å	T = 120 K
c = 18.2192 (17) Å	0.33 × 0.02 × 0.01 mm
β = 96.660 (5)°

Data collection top

Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer	2924 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1565 reflections with I > 2σ(I)
T_min = 0.786, T_max = 1.000	R_int = 0.146
14027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.096	11 restraints
wR(F²) = 0.223	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.P)² + 18.2957P] where P = (F_o² + 2F_c²)/3
2924 reflections	Δρ_max = 0.46 e Å⁻³
229 parameters	Δρ_min = −0.55 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.2444 (5)	0.37879 (12)	0.03537 (12)	0.0356 (6)
N1	1.3893 (15)	0.3016 (3)	0.4691 (4)	0.0277 (17)
H1N	1.492 (15)	0.299 (4)	0.513 (2)	0.033*
N2	0.8798 (14)	0.3126 (3)	0.2682 (4)	0.0242 (15)
H2N	0.891 (17)	0.283 (3)	0.233 (3)	0.029*
N3	0.6721 (14)	0.3622 (3)	0.2585 (4)	0.0268 (16)
C1	1.1941 (17)	0.3493 (4)	0.4555 (4)	0.0269 (19)
H1	1.1704	0.3806	0.4934	0.032*
C2	1.0242 (17)	0.3555 (4)	0.3889 (4)	0.0248 (19)
H2	0.8891	0.3912	0.3809	0.030*
C3	1.0490 (16)	0.3096 (4)	0.3328 (4)	0.0202 (17)
C4	1.2699 (17)	0.2574 (4)	0.3463 (4)	0.0230 (18)
C5	1.3246 (16)	0.2098 (4)	0.2931 (4)	0.0226 (18)
H5	1.2159	0.2107	0.2455	0.027*
C6	1.5348 (18)	0.1623 (4)	0.3100 (4)	0.0278 (19)
H6	1.5708	0.1303	0.2739	0.033*
C7	1.6980 (17)	0.1602 (4)	0.3803 (4)	0.0265 (19)
H7	1.8415	0.1266	0.3914	0.032*
C8	1.6507 (17)	0.2062 (4)	0.4325 (4)	0.0252 (19)
H8	1.7631	0.2054	0.4796	0.030*
C9	1.4343 (17)	0.2546 (4)	0.4157 (4)	0.0247 (19)
C10	0.5259 (16)	0.3655 (4)	0.1942 (5)	0.0259 (19)
H10	0.5643	0.3353	0.1565	0.031*
C11	0.3006 (18)	0.4161 (4)	0.1795 (4)	0.0263 (19)
C12	0.1484 (17)	0.4252 (4)	0.1102 (4)	0.0257 (19)
C13	−0.0717 (18)	0.4732 (4)	0.0953 (5)	0.034 (2)
H13	−0.1737	0.4784	0.0472	0.041*
C14	−0.1342 (18)	0.5130 (4)	0.1541 (5)	0.033 (2)
H14	−0.2819	0.5460	0.1458	0.040*
C15	0.0101 (19)	0.5057 (4)	0.2227 (5)	0.036 (2)
H15	−0.0375	0.5336	0.2616	0.043*
C16	0.2242 (18)	0.4586 (4)	0.2365 (5)	0.030 (2)
H16	0.3232	0.4543	0.2850	0.036*
Cl2	1.8077 (5)	0.28801 (11)	0.62092 (11)	0.0351 (6)
O1W	1.3131 (14)	0.3975 (3)	0.6374 (4)	0.0408 (16)
H1W	1.446 (13)	0.369 (3)	0.635 (6)	0.061*
H2W	1.150 (9)	0.379 (4)	0.640 (6)	0.061*
O2W	0.7300 (15)	0.4920 (3)	0.4565 (4)	0.0455 (17)
H3W	0.72 (2)	0.527 (3)	0.431 (5)	0.068*
H4W	0.563 (12)	0.484 (7)	0.469 (8)	0.068*	0.50
H5W	0.85 (3)	0.495 (7)	0.494 (5)	0.068*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0366 (12)	0.0402 (13)	0.0283 (11)	0.0061 (11)	−0.0034 (9)	−0.0028 (10)
N1	0.031 (4)	0.028 (4)	0.022 (4)	0.004 (3)	−0.007 (3)	0.003 (3)
N2	0.026 (4)	0.024 (4)	0.022 (4)	−0.002 (3)	−0.001 (3)	−0.002 (3)
N3	0.024 (4)	0.027 (4)	0.027 (4)	0.000 (3)	−0.005 (3)	0.005 (3)
C1	0.030 (5)	0.035 (5)	0.015 (4)	0.001 (4)	−0.002 (4)	0.002 (4)
C2	0.027 (4)	0.018 (4)	0.030 (5)	0.002 (4)	0.005 (4)	−0.002 (4)
C3	0.020 (4)	0.020 (4)	0.020 (4)	−0.003 (3)	0.001 (3)	0.002 (3)
C4	0.028 (4)	0.023 (5)	0.016 (4)	0.000 (4)	−0.004 (3)	0.008 (3)
C5	0.021 (4)	0.028 (5)	0.019 (4)	0.000 (4)	0.002 (3)	0.001 (4)
C6	0.031 (5)	0.022 (5)	0.030 (5)	0.002 (4)	0.003 (4)	0.000 (4)
C7	0.024 (4)	0.029 (5)	0.025 (4)	0.004 (4)	−0.002 (3)	0.010 (4)
C8	0.027 (4)	0.035 (5)	0.013 (4)	−0.007 (4)	−0.003 (3)	0.001 (4)
C9	0.027 (4)	0.029 (5)	0.017 (4)	0.000 (4)	−0.002 (3)	0.004 (4)
C10	0.023 (4)	0.021 (5)	0.032 (5)	−0.005 (4)	−0.002 (4)	0.001 (4)
C11	0.031 (5)	0.022 (5)	0.025 (4)	−0.006 (4)	0.002 (4)	0.002 (4)
C12	0.026 (4)	0.023 (5)	0.028 (5)	−0.003 (4)	0.003 (4)	0.001 (4)
C13	0.026 (5)	0.030 (5)	0.045 (6)	−0.003 (4)	−0.004 (4)	0.013 (4)
C14	0.024 (4)	0.024 (5)	0.052 (6)	0.006 (4)	0.006 (4)	0.008 (4)
C15	0.038 (5)	0.029 (5)	0.042 (6)	0.002 (4)	0.010 (5)	0.001 (4)
C16	0.024 (4)	0.034 (5)	0.032 (5)	0.000 (4)	0.002 (4)	0.002 (4)
Cl2	0.0372 (12)	0.0408 (13)	0.0258 (11)	−0.0028 (11)	−0.0026 (9)	0.0033 (10)
O1W	0.043 (4)	0.046 (4)	0.034 (4)	0.001 (3)	0.009 (3)	0.006 (3)
O2W	0.057 (4)	0.033 (4)	0.049 (4)	0.009 (4)	0.018 (4)	0.007 (3)

Geometric parameters (Å, º) top

Cl1—C12	1.752 (8)	C7—H7	0.9500
N1—C1	1.319 (10)	C8—C9	1.401 (11)
N1—C9	1.390 (10)	C8—H8	0.9500
N1—H1N	0.882 (10)	C10—C11	1.456 (11)
N2—C3	1.335 (9)	C10—H10	0.9500
N2—N3	1.380 (9)	C11—C12	1.382 (11)
N2—H2N	0.880 (10)	C11—C16	1.421 (12)
N3—C10	1.284 (10)	C12—C13	1.404 (11)
C1—C2	1.371 (10)	C13—C14	1.393 (12)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.392 (10)	C14—C15	1.353 (12)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.463 (11)	C15—C16	1.369 (12)
C4—C9	1.398 (10)	C15—H15	0.9500
C4—C5	1.406 (11)	C16—H16	0.9500
C5—C6	1.370 (11)	O1W—H1W	0.842 (10)
C5—H5	0.9500	O1W—H2W	0.840 (10)
C6—C7	1.407 (11)	O2W—H3W	0.841 (10)
C6—H6	0.9500	O2W—H4W	0.841 (11)
C7—C8	1.363 (11)	O2W—H5W	0.840 (10)

C1—N1—C9	121.3 (7)	C9—C8—H8	120.4
C1—N1—H1N	120 (6)	N1—C9—C4	119.8 (7)
C9—N1—H1N	119 (6)	N1—C9—C8	118.8 (7)
C3—N2—N3	117.9 (6)	C4—C9—C8	121.4 (7)
C3—N2—H2N	123 (5)	N3—C10—C11	119.3 (8)
N3—N2—H2N	119 (5)	N3—C10—H10	120.4
C10—N3—N2	115.8 (7)	C11—C10—H10	120.4
N1—C1—C2	122.5 (8)	C12—C11—C16	116.5 (8)
N1—C1—H1	118.7	C12—C11—C10	122.2 (8)
C2—C1—H1	118.7	C16—C11—C10	121.3 (7)
C1—C2—C3	120.2 (8)	C11—C12—C13	123.0 (8)
C1—C2—H2	119.9	C11—C12—Cl1	119.6 (6)
C3—C2—H2	119.9	C13—C12—Cl1	117.3 (6)
N2—C3—C2	121.9 (7)	C14—C13—C12	117.1 (8)
N2—C3—C4	120.1 (7)	C14—C13—H13	121.4
C2—C3—C4	118.0 (7)	C12—C13—H13	121.4
C9—C4—C5	118.3 (7)	C15—C14—C13	121.6 (8)
C9—C4—C3	118.2 (7)	C15—C14—H14	119.2
C5—C4—C3	123.4 (7)	C13—C14—H14	119.2
C6—C5—C4	120.0 (7)	C14—C15—C16	120.7 (9)
C6—C5—H5	120.0	C14—C15—H15	119.7
C4—C5—H5	120.0	C16—C15—H15	119.7
C5—C6—C7	120.9 (8)	C15—C16—C11	121.1 (8)
C5—C6—H6	119.6	C15—C16—H16	119.5
C7—C6—H6	119.6	C11—C16—H16	119.5
C8—C7—C6	120.2 (8)	H1W—O1W—H2W	111 (6)
C8—C7—H7	119.9	H3W—O2W—H4W	108 (6)
C6—C7—H7	119.9	H3W—O2W—H5W	112 (6)
C7—C8—C9	119.2 (7)	H4W—O2W—H5W	110 (6)
C7—C8—H8	120.4

C3—N2—N3—C10	176.2 (7)	C3—C4—C9—N1	−1.4 (11)
C9—N1—C1—C2	0.3 (13)	C5—C4—C9—C8	0.6 (12)
N1—C1—C2—C3	1.4 (13)	C3—C4—C9—C8	−179.7 (7)
N3—N2—C3—C2	−1.3 (11)	C7—C8—C9—N1	−179.5 (7)
N3—N2—C3—C4	179.2 (7)	C7—C8—C9—C4	−1.2 (12)
C1—C2—C3—N2	177.5 (7)	N2—N3—C10—C11	179.5 (7)
C1—C2—C3—C4	−3.0 (11)	N3—C10—C11—C12	175.7 (8)
N2—C3—C4—C9	−177.5 (7)	N3—C10—C11—C16	−4.8 (12)
C2—C3—C4—C9	2.9 (11)	C16—C11—C12—C13	−0.2 (12)
N2—C3—C4—C5	2.2 (12)	C10—C11—C12—C13	179.3 (8)
C2—C3—C4—C5	−177.3 (7)	C16—C11—C12—Cl1	175.8 (6)
C9—C4—C5—C6	0.0 (12)	C10—C11—C12—Cl1	−4.7 (11)
C3—C4—C5—C6	−179.7 (7)	C11—C12—C13—C14	0.2 (12)
C4—C5—C6—C7	0.0 (12)	Cl1—C12—C13—C14	−175.9 (6)
C5—C6—C7—C8	−0.7 (13)	C12—C13—C14—C15	−0.1 (13)
C6—C7—C8—C9	1.2 (12)	C13—C14—C15—C16	0.0 (14)
C1—N1—C9—C4	−0.2 (12)	C14—C15—C16—C11	0.0 (13)
C1—N1—C9—C8	178.1 (8)	C12—C11—C16—C15	0.1 (12)
C5—C4—C9—N1	178.9 (7)	C10—C11—C16—C15	−179.3 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···Cl2	0.88 (5)	2.32 (5)	3.192 (7)	173 (6)
O1w—H1w···Cl2	0.84 (6)	2.37 (6)	3.207 (7)	177 (11)
N2—H2n···Cl2ⁱ	0.88 (6)	2.49 (6)	3.349 (7)	166 (7)
O1w—H2w···Cl2ⁱⁱ	0.84 (5)	2.42 (7)	3.192 (7)	154 (8)
O2w—H3w···O1wⁱⁱⁱ	0.84 (7)	1.96 (7)	2.801 (9)	174 (10)
O2w—H4w···O2w^iv	0.84 (8)	2.08 (10)	2.804 (10)	144 (11)
O2w—H5w···O2wⁱⁱⁱ	0.83 (12)	2.05 (13)	2.804 (10)	151 (10)

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₃⁺·Cl⁻·2H₂O
M_r	354.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	4.5946 (3), 20.1550 (19), 18.2192 (17)
β (°)	96.660 (5)
V (Å³)	1675.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.33 × 0.02 × 0.01

Data collection
Diffractometer	Bruker–Nonius Roper CCD camera on a κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.786, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14027, 2924, 1565
R_int	0.146
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.096, 0.223, 1.06
No. of reflections	2924
No. of parameters	229
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.P)² + 18.2957P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.55

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···Cl2	0.88 (5)	2.32 (5)	3.192 (7)	173 (6)
O1w—H1w···Cl2	0.84 (6)	2.37 (6)	3.207 (7)	177 (11)
N2—H2n···Cl2ⁱ	0.88 (6)	2.49 (6)	3.349 (7)	166 (7)
O1w—H2w···Cl2ⁱⁱ	0.84 (5)	2.42 (7)	3.192 (7)	154 (8)
O2w—H3w···O1wⁱⁱⁱ	0.84 (7)	1.96 (7)	2.801 (9)	174 (10)
O2w—H4w···O2w^iv	0.84 (8)	2.08 (10)	2.804 (10)	144 (11)
O2w—H5w···O2wⁱⁱⁱ	0.83 (12)	2.05 (13)	2.804 (10)	151 (10)

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x−1, y, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Volume 68| Part 6| June 2012| Pages o1850-o1851

doi:10.1107/S1600536812022660

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[(E)-2-(2-Chloro­benzyl­­idene)hydrazin-1-yl]quinolin-1-ium chloride dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[(E)-2-(2-Chlorobenzylidene)hydrazin-1-yl]quinolin-1-ium chloride dihydrate