7-Chloro-4-(2-hy-droxy-ethyl-amino)-quinolin-1-ium chloride.

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 hy-droxy-ethyl group is approximately perpendicular to this plane [Cring-N-Cmethyl-ene-C torsion angle = -74.61 (18)°]. A supra-molecular 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(hy-droxy) inter-actions.

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 = 259.13

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.07

2581 reflections

154 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536814004565/hg5387sup1.cif

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

Click here for additional data file.

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

CCDC reference: 988939

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H12ClN2O+·Cl−	F(000) = 536
Mr = 259.13	Dx = 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

Rigaku R-AXIS conversion diffractometer	2581 independent reflections
Radiation source: Sealed Tube	2162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 10.0000 pixels mm-1	θmax = 27.5°, θmin = 2.5°
profile data from ω–scans	h = −10→9
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2013)	k = −20→21
Tmin = 0.831, Tmax = 1.000	l = −11→11
7784 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)] = 0.030	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(Fo2) + (0.0353P)2 + 0.170P] where P = (Fo2 + 2Fc2)/3
2581 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.37 e Å−3
3 restraints	Δρmin = −0.24 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	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)

	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)

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)

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

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) ; (ii) ; (iii) .