7-Chloro-4-(2-hy­droxy­ethyl­amino)­quinolin-1-ium chloride

Gama, I.L.; Souza, M.V.N. de; Wardell, J.L.; Tiekink, E.R.T.

doi:10.1107/S1600536814004565

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o385-o386

doi:10.1107/S1600536814004565

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7-Chloro-4-(2-hydroxyethylamino)quinolin-1-ium chloride

Ivson L. Gama,^a Marcus V. N. de Souza,^a James L. Wardell ^a,^b ‡ and Edward R. T. Tiekink ^c ^*

^aFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos–Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, ^bChemistry Department, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 February 2014; accepted 27 February 2014; online 5 March 2014)

In the title salt, C₁₁H₁₂ClN₂O⁺·Cl⁻, the ten non-H atoms comprising the quinolinium residue are coplanar (r.m.s. deviation = 0.041 Å) and the hydroxyethyl group is approximately perpendicular to this plane [C_ring—N—C_methylene—C torsion angle = −74.61 (18)°]. A supramolecular chain aligned along [101] mediated by charge-assisted O/N—H⋯Cl⁻ hydrogen bonds features in the crystal packing. Chains are connected into a three-dimensional architecture by C—H⋯O(hydroxy) interactions.

CCDC reference: 988939

Related literature

For the wide range of pharmacological activities of synthetic and natural products containing the quinoline nucleus, see: Andrade et al. (2007 ); Cunico et al. (2006 ); Font et al. (1997 ); Kaminsky & Meltzer (1968 ); Musiol et al. (2006 ); Nakamura et al. (1999 ); Sloboda et al., (1991 ); de Souza et al. (2014 ); Tanenbaum & Tuffanelli (1980 ); Warshakoon et al. (2006 ). For the crystal structures of related 4-RN(H)-7-chloroquinolines, see: Kaiser et al., (2009 ).

Experimental

Crystal data

C₁₁H₁₂ClN₂O⁺·Cl⁻
M_r = 259.13
Monoclinic, P 2₁ /c
a = 8.2438 (13) Å
b = 16.405 (2) Å
c = 8.8561 (14) Å
β = 110.705 (2)°
V = 1120.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 100 K
0.20 × 0.07 × 0.04 mm

Data collection

Rigaku R-AXIS conversion diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2013 ) T_min = 0.831, T_max = 1.000
7784 measured reflections
2581 independent reflections
2162 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.076
S = 1.07
2581 reflections
154 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯Cl2	0.84 (2)	2.30 (2)	3.1338 (14)	179 (2)
N1—H1n⋯Cl2ⁱ	0.88 (1)	2.29 (1)	3.1602 (15)	168 (1)
N2—H2n⋯Cl2ⁱⁱ	0.87 (1)	2.49 (2)	3.2949 (14)	154 (2)
C2—H2⋯O1ⁱⁱⁱ	0.95	2.60	3.545 (2)	173
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 988939

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536814004565/hg5387sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004565/hg5387Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004565/hg5387Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

A solution of 7-chloro-4-(2-hydroxyethylamino)quinoline (1 mmol) and FeCl₃.6H₂O (1 mmol) in EtOH (25 ml) was refluxed for 30 min. On leaving the reaction mixture at room temperature, crystals of the title compound were formed, M.pt: 538–541 K (dec.).

Refinement top

Intensity data was collected at the National Crystallographic Service, England (Coles & Gale, 2012). The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with U_iso(H) = 1.2U_eq(C). The O- and N-bound H atoms were located from a difference map and refined with O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, respectively, and with U_iso(H) = 1.5U_eq(O) and 1.2U_eq(N), respectively.

Results and discussion top

The quinoline nucleus is found in many synthetic and natural products having a wide range of pharmacological activities, such as anti-viral (Font et al., 1997), anti-cancer (Nakamura et al., 1999; de Souza et al., 2014), anti-bacterial (Kaminsky & Meltzer, 1968), anti-malarial (Tanenbaum & Tuffanelli, 1980; Cunico et al., 2006; Andrade et al., 2007), anti-fungal (Musiol et al., 2006), anti-obesity (Warshakoon et al., 2006) and anti-inflammatory (Sloboda et al., 1991) activities. The crystal structures of a series of 4-RN(H)-7-chloro-quinolines was recently reported (Kaiser et al., 2009). We now wish to report the crystal structure of the HCl salt of 4-(HOCH₂CH₂NH-7-chloro-quinoline, (I), obtained serendipiously from an attempted reaction to generate an iron complex.

The components of salt (I) are illustrated in Fig. 1. The 10 non-hydrogen atoms comprising the quinolinium residue are co-planar with a r.m.s. deviation of 0.041 Å. The hydroxyethyl group is almost perpendicular to this plane as seen in the C3—N2—C10—C11 torsion angle of -74.61 (18)°.

In the crystal structure, charge-assisted O, N—H···Cl^- hydrogen bonds, Table 1, lead to a supramolecular chain aligned along [1 0 1], Fig. 2. These are connected into a three-dimensional architecture by methylene-C—H···O(hydroxyl) interactions, Fig. 3 & Table 1.

Related literature top

For a wide range of pharmacological activities of synthetic and natural products containing the quinoline nucleus, see: Andrade et al. (2007); Cunico et al. (2006); Font et al. (1997); Kaminsky & Meltzer (1968); Musiol et al. (2006); Nakamura et al. (1999); Sloboda et al., (1991); de Souza et al. (2014); Tanenbaum & Tuffanelli (1980); Warshakoon et al. (2006). For the crystal structures of related 4-RN(H)-7-chloroquinolines, see: Kaiser et al., (2009).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2013); cell refinement: CrystalClear-SM Expert (Rigaku, 2013); data reduction: CrystalClear-SM Expert (Rigaku, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the ions in (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	Fig. 2. A view of the supramolecular chain along [1 0 1] in (I) showing O—H···Cl^- and N—H···Cl^- hydrogen bonds as orange and blue dashed lines, respectively.
	Fig. 3. A view in projection down [1 0 1], the direction of the chain shown in Fig. 2, of the unit-cell contents of (I). The O—H···Cl^-, N—H···Cl^- and C—H···O interactions are shown as orange, blue and green dashed lines, respectively.

7-Chloro-4-(2-hydroxyethylamino)quinolin-1-ium chloride top

Crystal data top

C₁₁H₁₂ClN₂O⁺·Cl⁻	F(000) = 536
M_r = 259.13	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 14670 reflections
a = 8.2438 (13) Å	θ = 3.0–27.5°
b = 16.405 (2) Å	µ = 0.56 mm⁻¹
c = 8.8561 (14) Å	T = 100 K
β = 110.705 (2)°	Prism, colourless
V = 1120.3 (3) Å³	0.20 × 0.07 × 0.04 mm
Z = 4

Data collection top

Rigaku R-AXIS conversion diffractometer	2581 independent reflections
Radiation source: Sealed Tube	2162 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10.0000 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
profile data from ω–scans	h = −10→9
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2013)	k = −20→21
T_min = 0.831, T_max = 1.000	l = −11→11
7784 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0353P)² + 0.170P] where P = (F_o² + 2F_c²)/3
2581 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.37 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₁H₁₂ClN₂O⁺·Cl⁻	V = 1120.3 (3) Å³
M_r = 259.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2438 (13) Å	µ = 0.56 mm⁻¹
b = 16.405 (2) Å	T = 100 K
c = 8.8561 (14) Å	0.20 × 0.07 × 0.04 mm
β = 110.705 (2)°

Data collection top

Rigaku R-AXIS conversion diffractometer	2581 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2013)	2162 reflections with I > 2σ(I)
T_min = 0.831, T_max = 1.000	R_int = 0.036
7784 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	3 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.37 e Å⁻³
2581 reflections	Δρ_min = −0.24 e Å⁻³
154 parameters

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
Cl1	1.02274 (5)	0.76756 (2)	0.47284 (4)	0.01888 (11)
O1	0.53371 (15)	0.30013 (7)	0.03702 (13)	0.0206 (3)
H1O	0.595 (2)	0.3400 (9)	0.033 (2)	0.031*
N1	0.90024 (17)	0.49718 (8)	0.69236 (15)	0.0153 (3)
H1N	0.9879 (17)	0.5083 (11)	0.7812 (14)	0.018*
N2	0.50113 (17)	0.43490 (8)	0.27207 (15)	0.0153 (3)
H2N	0.466 (2)	0.4713 (9)	0.1961 (17)	0.018*
C1	0.8212 (2)	0.42491 (10)	0.67877 (18)	0.0162 (3)
H1	0.8571	0.3886	0.7681	0.019*
C2	0.6904 (2)	0.40138 (9)	0.54089 (18)	0.0152 (3)
H2	0.6387	0.3492	0.5354	0.018*
C3	0.63187 (19)	0.45441 (9)	0.40638 (17)	0.0131 (3)
C4	0.72227 (19)	0.53172 (9)	0.41947 (18)	0.0135 (3)
C5	0.68800 (19)	0.58698 (9)	0.28956 (17)	0.0145 (3)
H5	0.5992	0.5747	0.1895	0.017*
C6	0.7804 (2)	0.65795 (9)	0.30511 (18)	0.0157 (3)
H6	0.7581	0.6940	0.2160	0.019*
C7	0.90831 (19)	0.67665 (9)	0.45450 (18)	0.0154 (3)
C8	0.94774 (19)	0.62514 (9)	0.58444 (18)	0.0153 (3)
H8	1.0349	0.6389	0.6845	0.018*
C9	0.85580 (19)	0.55131 (9)	0.56571 (17)	0.0133 (3)
C10	0.4232 (2)	0.35374 (9)	0.24153 (19)	0.0172 (3)
H10A	0.3101	0.3569	0.1517	0.021*
H10B	0.4014	0.3348	0.3388	0.021*
C11	0.5388 (2)	0.29206 (10)	0.19883 (18)	0.0177 (3)
H11A	0.6598	0.2992	0.2736	0.021*
H11B	0.5014	0.2363	0.2144	0.021*
Cl2	0.75804 (5)	0.45204 (2)	0.02211 (4)	0.01726 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0192 (2)	0.01435 (19)	0.02016 (19)	−0.00294 (15)	0.00339 (15)	0.00041 (15)
O1	0.0244 (6)	0.0209 (6)	0.0164 (5)	−0.0031 (5)	0.0071 (5)	−0.0019 (5)
N1	0.0159 (6)	0.0175 (7)	0.0112 (6)	0.0010 (5)	0.0030 (5)	0.0010 (5)
N2	0.0163 (6)	0.0137 (7)	0.0140 (6)	0.0000 (5)	0.0029 (5)	0.0005 (5)
C1	0.0194 (8)	0.0160 (7)	0.0146 (7)	0.0032 (6)	0.0079 (6)	0.0021 (6)
C2	0.0175 (7)	0.0133 (7)	0.0162 (7)	0.0000 (6)	0.0077 (6)	0.0008 (6)
C3	0.0130 (7)	0.0139 (7)	0.0138 (7)	0.0031 (6)	0.0064 (6)	−0.0010 (6)
C4	0.0133 (7)	0.0139 (7)	0.0141 (7)	0.0014 (6)	0.0058 (6)	−0.0016 (6)
C5	0.0143 (7)	0.0151 (7)	0.0120 (7)	0.0021 (6)	0.0021 (6)	−0.0012 (6)
C6	0.0160 (7)	0.0148 (7)	0.0158 (7)	0.0029 (6)	0.0050 (6)	0.0025 (6)
C7	0.0152 (7)	0.0126 (7)	0.0196 (7)	−0.0003 (6)	0.0078 (6)	−0.0016 (6)
C8	0.0133 (7)	0.0173 (8)	0.0143 (7)	0.0011 (6)	0.0035 (6)	−0.0021 (6)
C9	0.0144 (7)	0.0133 (7)	0.0131 (7)	0.0035 (6)	0.0060 (6)	0.0000 (6)
C10	0.0177 (8)	0.0156 (8)	0.0177 (7)	−0.0043 (6)	0.0053 (6)	−0.0034 (6)
C11	0.0209 (8)	0.0159 (8)	0.0164 (7)	−0.0023 (6)	0.0066 (6)	−0.0002 (6)
Cl2	0.01711 (19)	0.0195 (2)	0.01341 (17)	0.00029 (15)	0.00320 (14)	−0.00020 (14)

Geometric parameters (Å, º) top

Cl1—C7	1.7413 (16)	C4—C9	1.409 (2)
O1—C11	1.4250 (18)	C4—C5	1.413 (2)
O1—H1O	0.838 (9)	C5—C6	1.371 (2)
N1—C1	1.338 (2)	C5—H5	0.9500
N1—C9	1.3749 (19)	C6—C7	1.404 (2)
N1—H1N	0.879 (9)	C6—H6	0.9500
N2—C3	1.331 (2)	C7—C8	1.371 (2)
N2—C10	1.4615 (19)	C8—C9	1.407 (2)
N2—H2N	0.869 (9)	C8—H8	0.9500
C1—C2	1.368 (2)	C10—C11	1.526 (2)
C1—H1	0.9500	C10—H10A	0.9900
C2—C3	1.415 (2)	C10—H10B	0.9900
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.455 (2)	C11—H11B	0.9900

C11—O1—H1O	108.4 (14)	C5—C6—H6	120.5
C1—N1—C9	121.21 (13)	C7—C6—H6	120.5
C1—N1—H1N	119.0 (12)	C8—C7—C6	122.19 (14)
C9—N1—H1N	119.6 (12)	C8—C7—Cl1	119.32 (12)
C3—N2—C10	123.26 (13)	C6—C7—Cl1	118.48 (12)
C3—N2—H2N	117.9 (12)	C7—C8—C9	118.27 (14)
C10—N2—H2N	118.6 (12)	C7—C8—H8	120.9
N1—C1—C2	122.38 (14)	C9—C8—H8	120.9
N1—C1—H1	118.8	N1—C9—C8	118.87 (13)
C2—C1—H1	118.8	N1—C9—C4	119.93 (14)
C1—C2—C3	120.30 (14)	C8—C9—C4	121.20 (14)
C1—C2—H2	119.8	N2—C10—C11	112.19 (13)
C3—C2—H2	119.8	N2—C10—H10A	109.2
N2—C3—C2	122.13 (14)	C11—C10—H10A	109.2
N2—C3—C4	120.72 (13)	N2—C10—H10B	109.2
C2—C3—C4	117.15 (13)	C11—C10—H10B	109.2
C9—C4—C5	117.95 (14)	H10A—C10—H10B	107.9
C9—C4—C3	118.95 (13)	O1—C11—C10	112.87 (13)
C5—C4—C3	123.05 (14)	O1—C11—H11A	109.0
C6—C5—C4	121.27 (14)	C10—C11—H11A	109.0
C6—C5—H5	119.4	O1—C11—H11B	109.0
C4—C5—H5	119.4	C10—C11—H11B	109.0
C5—C6—C7	119.06 (14)	H11A—C11—H11B	107.8

C9—N1—C1—C2	−1.4 (2)	C5—C6—C7—Cl1	−179.28 (11)
N1—C1—C2—C3	−0.9 (2)	C6—C7—C8—C9	0.0 (2)
C10—N2—C3—C2	−9.1 (2)	Cl1—C7—C8—C9	−178.78 (11)
C10—N2—C3—C4	170.11 (13)	C1—N1—C9—C8	−177.54 (14)
C1—C2—C3—N2	−177.69 (14)	C1—N1—C9—C4	1.4 (2)
C1—C2—C3—C4	3.0 (2)	C7—C8—C9—N1	176.63 (13)
N2—C3—C4—C9	177.74 (13)	C7—C8—C9—C4	−2.3 (2)
C2—C3—C4—C9	−3.0 (2)	C5—C4—C9—N1	−176.31 (13)
N2—C3—C4—C5	−5.2 (2)	C3—C4—C9—N1	0.9 (2)
C2—C3—C4—C5	174.04 (13)	C5—C4—C9—C8	2.6 (2)
C9—C4—C5—C6	−0.6 (2)	C3—C4—C9—C8	179.74 (13)
C3—C4—C5—C6	−177.64 (14)	C3—N2—C10—C11	−74.61 (18)
C4—C5—C6—C7	−1.6 (2)	N2—C10—C11—O1	−77.07 (16)
C5—C6—C7—C8	2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···Cl2	0.84 (2)	2.30 (2)	3.1338 (14)	179 (2)
N1—H1n···Cl2ⁱ	0.88 (1)	2.29 (1)	3.1602 (15)	168 (1)
N2—H2n···Cl2ⁱⁱ	0.87 (1)	2.49 (2)	3.2949 (14)	154 (2)
C2—H2···O1ⁱⁱⁱ	0.95	2.60	3.545 (2)	173

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···Cl2	0.835 (16)	2.299 (16)	3.1338 (14)	178.5 (17)
N1—H1n···Cl2ⁱ	0.879 (13)	2.294 (14)	3.1602 (15)	168.4 (12)
N2—H2n···Cl2ⁱⁱ	0.869 (14)	2.491 (15)	3.2949 (14)	154.2 (15)
C2—H2···O1ⁱⁱⁱ	0.95	2.60	3.545 (2)	173

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

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 (Coles & Gale, 2012 ), and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Structural studies are supported by the Ministry of Higher Education (Malaysia) and the University of Malaya through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/3).

References

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Volume 70| Part 4| April 2014| Pages o385-o386

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