Literature DB >> 21578845

4-[(2-Chloro-ethyl)amino]quinolinium chloride monohydrate.

Marcus V N de Souza, Edward R T Tiekink, James L Wardell, Solange M S V Wardell.

Abstract

In the title salt hydrate, C(11)H(12)ClN(2) (+)·Cl(-)·H(2)O, the n class="Chemical">quinolin-ium core is essentially planar (r.m.s. deviation = 0.027 Å) with the chloro-ethyl side chain being almost orthogonal to the core [C-N-C-C torsion angle = -80.0 (3)°]. In the crystal packing, the water mol-ecule bridges three species, forming donor inter-actions to two chloride anions and accepting a hydrogen bond from the quinolinium H atom. The chloride anion accepts a hydrogen bond from the amine N atom with the result that a two-dimensional supra-molecular array is formed in the ac plane. A C-H⋯Cl interaction also occurs.

Entities: Chemical Disease Gene Species

Year: 2009 PMID： 21578845 PMCID： PMC2971810 DOI： 10.1107/S160053680904834X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to malaria, see: Snow et al. (1999 ▶); Breman (2001 ▶); World Health Organization (1999 ▶). For background information on the pharmacological activity of n class="Chemical">quinoline derivatives, see: Elslager et al. (1969 ▶); Font et al. (1997 ▶); Kaminsky & Meltzer (1968 ▶); Musiol et al. (2006 ▶); Nakamura et al. (1999 ▶); Palmer et al. (1993 ▶); Ridley (2002 ▶); Sloboda et al. (1991 ▶); Tanenbaum & Tuffanelli (1980 ▶); Warshakoon et al. (2006 ▶). For recent studies on quinoline-based anti-malarials, see: Andrade et al. (2007 ▶); Cunico et al. (2006 ▶); da Silva et al. (2003 ▶); de Souza et al. (2005 ▶). For a related crystallographic study on a neutral species related to the title compound, see: Kaiser et al. (2009 ▶). For the synthesis, see: Elderfield et al. (1946 ▶).

Experimental

Crystal data

C11H12ClN2 +·Cl−·H2O M = 261.14 Orthorhombic, a = 18.7513 (7) Å b = 14.1030 (5) Å c = 4.606 (1) Å V = 1218.1 (3) Å3 Z = 4 Mo Kα radiation μ = 0.51 mm−1 T = 120 K 0.46 × 0.03 × 0.03 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.816, T max = 1 11264 measured reflections 2681 independent reflections 2390 reflections with I > 2σ(I) R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.065 S = 1.06 2681 reflections 151 parameters 4 restraints H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.21 e Å−3 Absolute structure: Flack (1983 ▶), 1123 Friedel pairs Flack parameter: 0.03 (6) 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: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904834X/hg2592sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680904834X/hg2592Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₁₂ClN₂⁺·Cl⁻·H₂O	F(000) = 544
M_r = 261.14	D_x = 1.424 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2c -2n	Cell parameters from 1650 reflections
a = 18.7513 (7) Å	θ = 2.9–27.5°
b = 14.1030 (5) Å	µ = 0.51 mm⁻¹
c = 4.606 (1) Å	T = 120 K
V = 1218.1 (3) Å³	Needle, colourless
Z = 4	0.46 × 0.03 × 0.03 mm

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2681 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2390 reflections with I > 2σ(I)
graphite	R_int = 0.049
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
φ & ω scans	h = −19→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −18→18
T_min = 0.816, T_max = 1	l = −5→5
11264 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0173P)² + 0.5206P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2681 reflections	Δρ_max = 0.22 e Å⁻³
151 parameters	Δρ_min = −0.21 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1123 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	U_iso*/U_eq
Cl1	0.13741 (3)	0.81412 (4)	0.18205 (16)	0.02165 (12)
Cl2	0.21007 (3)	0.53250 (3)	0.01935 (15)	0.02136 (12)
O1	0.10851 (8)	0.59720 (11)	0.5181 (4)	0.0271 (4)
H1W	0.1283	0.5858	0.6780	0.041*
H2W	0.1365	0.5852	0.3805	0.041*
N1	0.48246 (10)	0.82732 (12)	0.3467 (4)	0.0188 (4)
H1	0.5241	0.8470	0.4104	0.023*
N2	0.29024 (9)	0.73519 (11)	0.0155 (4)	0.0163 (3)
H2	0.2742	0.6796	0.0728	0.020*
C1	0.44596 (12)	0.88075 (15)	0.1575 (5)	0.0203 (5)
H1A	0.4657	0.9397	0.0982	0.024*
C2	0.38179 (12)	0.85382 (14)	0.0472 (5)	0.0184 (4)
H2A	0.3572	0.8943	−0.0839	0.022*
C3	0.35148 (11)	0.76568 (14)	0.1268 (4)	0.0158 (5)
C4	0.39002 (11)	0.70904 (15)	0.3390 (5)	0.0152 (4)
C5	0.36387 (12)	0.62250 (15)	0.4527 (4)	0.0179 (5)
H5	0.3194	0.5985	0.3873	0.021*
C6	0.40215 (12)	0.57290 (15)	0.6566 (5)	0.0208 (5)
H6	0.3837	0.5153	0.7328	0.025*
C7	0.46856 (13)	0.60686 (16)	0.7533 (5)	0.0230 (5)
H7	0.4951	0.5715	0.8917	0.028*
C8	0.49518 (11)	0.69039 (15)	0.6493 (5)	0.0192 (5)
H8	0.5399	0.7133	0.7159	0.023*
C9	0.45584 (11)	0.74244 (15)	0.4426 (4)	0.0158 (5)
C10	0.24785 (13)	0.78772 (16)	−0.1954 (5)	0.0181 (5)
H10A	0.2162	0.7429	−0.2993	0.022*
H10B	0.2802	0.8167	−0.3402	0.022*
C11	0.20268 (11)	0.86510 (15)	−0.0584 (4)	0.0177 (5)
H11A	0.1783	0.9017	−0.2125	0.021*
H11B	0.2337	0.9091	0.0515	0.021*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0166 (3)	0.0257 (3)	0.0227 (3)	−0.0021 (2)	0.0006 (2)	0.0039 (3)
Cl2	0.0218 (3)	0.0193 (2)	0.0230 (3)	−0.0009 (2)	−0.0043 (2)	0.0008 (3)
O1	0.0220 (9)	0.0335 (9)	0.0258 (8)	0.0085 (7)	0.0002 (8)	0.0060 (9)
N1	0.0138 (10)	0.0193 (10)	0.0234 (10)	−0.0035 (8)	−0.0001 (8)	−0.0019 (8)
N2	0.0164 (9)	0.0140 (8)	0.0186 (8)	0.0010 (7)	−0.0025 (8)	0.0033 (9)
C1	0.0211 (11)	0.0162 (10)	0.0235 (11)	−0.0012 (9)	0.0026 (10)	0.0002 (10)
C2	0.0187 (11)	0.0169 (10)	0.0196 (11)	0.0036 (9)	0.0018 (10)	0.0010 (10)
C3	0.0136 (11)	0.0169 (10)	0.0168 (12)	0.0041 (8)	0.0021 (8)	−0.0028 (8)
C4	0.0135 (11)	0.0158 (10)	0.0163 (11)	0.0040 (8)	0.0009 (8)	−0.0036 (8)
C5	0.0172 (12)	0.0158 (10)	0.0206 (12)	−0.0003 (9)	−0.0029 (8)	−0.0015 (9)
C6	0.0235 (12)	0.0156 (10)	0.0235 (11)	0.0031 (9)	−0.0009 (11)	0.0002 (10)
C7	0.0237 (13)	0.0235 (12)	0.0217 (13)	0.0108 (10)	−0.0031 (9)	−0.0017 (9)
C8	0.0139 (11)	0.0241 (11)	0.0196 (12)	0.0031 (9)	−0.0012 (10)	−0.0062 (9)
C9	0.0160 (11)	0.0162 (10)	0.0151 (11)	0.0020 (9)	0.0022 (8)	−0.0032 (8)
C10	0.0175 (12)	0.0193 (11)	0.0175 (11)	0.0016 (9)	−0.0032 (9)	0.0011 (8)
C11	0.0155 (12)	0.0186 (11)	0.0192 (12)	−0.0011 (9)	0.0009 (8)	0.0029 (8)

Cl1—C11	1.800 (2)	C4—C5	1.416 (3)
O1—H1W	0.8400	C5—C6	1.374 (3)
O1—H2W	0.8401	C5—H5	0.9500
N1—C1	1.340 (3)	C6—C7	1.407 (3)
N1—C9	1.370 (3)	C6—H6	0.9500
N1—H1	0.8800	C7—C8	1.366 (3)
N2—C3	1.329 (3)	C7—H7	0.9500
N2—C10	1.457 (3)	C8—C9	1.411 (3)
N2—H2	0.8800	C8—H8	0.9500
C1—C2	1.360 (3)	C10—C11	1.519 (3)
C1—H1A	0.9500	C10—H10A	0.9900
C2—C3	1.415 (3)	C10—H10B	0.9900
C2—H2A	0.9500	C11—H11A	0.9900
C3—C4	1.454 (3)	C11—H11B	0.9900
C4—C9	1.405 (3)

H1W—O1—H2W	110.3	C5—C6—H6	119.8
C1—N1—C9	121.00 (19)	C7—C6—H6	119.8
C1—N1—H1	119.5	C8—C7—C6	120.4 (2)
C9—N1—H1	119.5	C8—C7—H7	119.8
C3—N2—C10	124.33 (17)	C6—C7—H7	119.8
C3—N2—H2	117.8	C7—C8—C9	119.6 (2)
C10—N2—H2	117.8	C7—C8—H8	120.2
N1—C1—C2	122.5 (2)	C9—C8—H8	120.2
N1—C1—H1A	118.7	N1—C9—C4	120.24 (19)
C2—C1—H1A	118.7	N1—C9—C8	118.81 (19)
C1—C2—C3	120.2 (2)	C4—C9—C8	120.95 (19)
C1—C2—H2A	119.9	N2—C10—C11	113.12 (18)
C3—C2—H2A	119.9	N2—C10—H10A	109.0
N2—C3—C2	122.08 (19)	C11—C10—H10A	109.0
N2—C3—C4	120.73 (18)	N2—C10—H10B	109.0
C2—C3—C4	117.2 (2)	C11—C10—H10B	109.0
C9—C4—C5	117.89 (19)	H10A—C10—H10B	107.8
C9—C4—C3	118.74 (19)	C10—C11—Cl1	110.35 (15)
C5—C4—C3	123.36 (19)	C10—C11—H11A	109.6
C6—C5—C4	120.7 (2)	Cl1—C11—H11A	109.6
C6—C5—H5	119.6	C10—C11—H11B	109.6
C4—C5—H5	119.6	Cl1—C11—H11B	109.6
C5—C6—C7	120.4 (2)	H11A—C11—H11B	108.1

C9—N1—C1—C2	−1.0 (3)	C5—C6—C7—C8	1.2 (3)
N1—C1—C2—C3	−1.1 (4)	C6—C7—C8—C9	−0.4 (3)
C10—N2—C3—C2	−0.3 (3)	C1—N1—C9—C4	1.2 (3)
C10—N2—C3—C4	179.32 (19)	C1—N1—C9—C8	−177.8 (2)
C1—C2—C3—N2	−177.4 (2)	C5—C4—C9—N1	−177.87 (18)
C1—C2—C3—C4	2.9 (3)	C3—C4—C9—N1	0.7 (3)
N2—C3—C4—C9	177.64 (19)	C5—C4—C9—C8	1.2 (3)
C2—C3—C4—C9	−2.7 (3)	C3—C4—C9—C8	179.73 (18)
N2—C3—C4—C5	−3.9 (3)	C7—C8—C9—N1	178.23 (19)
C2—C3—C4—C5	175.8 (2)	C7—C8—C9—C4	−0.8 (3)
C9—C4—C5—C6	−0.4 (3)	C3—N2—C10—C11	−80.0 (3)
C3—C4—C5—C6	−178.9 (2)	N2—C10—C11—Cl1	−63.9 (2)
C4—C5—C6—C7	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.84	2.710 (2)	172
N2—H2···Cl2	0.88	2.41	3.2298 (18)	155
O1—H1w···Cl2ⁱⁱ	0.84	2.32	3.1288 (19)	161
O1—H2w···Cl2	0.84	2.29	3.1204 (19)	173
C5—H5···Cl2	0.95	2.82	3.730 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	1.84	2.710 (2)	172
N2—H2⋯Cl2	0.88	2.41	3.2298 (18)	155
O1—H1w⋯Cl2ⁱⁱ	0.84	2.32	3.1288 (19)	161
O1—H2w⋯Cl2	0.84	2.29	3.1204 (19)	173
C5—H5⋯Cl2	0.95	2.82	3.730 (2)	161

Symmetry codes: (i) ; (ii) .

16 in total

Review 1. Medical need, scientific opportunity and the drive for antimalarial drugs.

Authors: Robert G Ridley
Journal: Nature Date: 2002-02-07 Impact factor: 49.962

Review 2. New fluoroquinolones: a class of potent antibiotics.

Authors: Marcus Vinícius Nora De Souza
Journal: Mini Rev Med Chem Date: 2005-11 Impact factor: 3.862

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents.

Authors: Namal C Warshakoon; Justin Sheville; Ritu Tiku Bhatt; Wei Ji; Jose L Mendez-Andino; Kenneth M Meyers; Nick Kim; John A Wos; Chrissy Mitchell; Jennifer L Paris; Beth B Pinney; Ofer Reizes; X Eric Hu
Journal: Bioorg Med Chem Lett Date: 2006-07-25 Impact factor: 2.823

5. Enhanced activity of mefloquine and artesunic acid against Plasmodium falciparum in vitro and P. berghei in mice by combination with ciprofloxacin.

Authors: Anderson Assunção Andrade; Fernando de Pilla Varotti; Isabela Oliveira de Freitas; Marcus Vinícius Nora de Souza; Thatyana Rocha Alves Vasconcelos; Núbia Boechat; Antoniana Ursine Krettli
Journal: Eur J Pharmacol Date: 2006-12-12 Impact factor: 4.432

6. Quinolone antibacterial agents. Oxolinic acid and related compounds.

Authors: D Kaminsky; R I Meltzer
Journal: J Med Chem Date: 1968-01 Impact factor: 7.446

7. Antifungal properties of new series of quinoline derivatives.

Authors: Robert Musiol; Josef Jampilek; Vladimir Buchta; Luis Silva; Halina Niedbala; Barbara Podeszwa; Anna Palka; Katarzyna Majerz-Maniecka; Barbara Oleksyn; Jaroslaw Polanski
Journal: Bioorg Med Chem Date: 2006-02-03 Impact factor: 3.641

8. Direct interaction between a quinoline derivative, MS-209, and multidrug resistance protein (MRP) in human gastric cancer cells.

Authors: T Nakamura; M Oka; K Aizawa; H Soda; M Fukuda; K Terashi; K Ikeda; Y Mizuta; Y Noguchi; Y Kimura; T Tsuruo; S Kohno
Journal: Biochem Biophys Res Commun Date: 1999-02-24 Impact factor: 3.575

Review 9. Biological activity and synthetic metodologies for the preparation of fluoroquinolones, a class of potent antibacterial agents.

Authors: Adilson D Da Silva; Mauro V De Almeida; Marcus V N De Souza; Mara R C Couri
Journal: Curr Med Chem Date: 2003-01 Impact factor: 4.530

10. Repository drugs. 8. Ester and amide congeners of amodiaquine, hydroxychloroquine, oxychloroquine, primaquine, quinacrine, and related substances as potential long-acting antimalarial agents.

Authors: E F Elslager; F H Tendick; L M Werbel
Journal: J Med Chem Date: 1969-07 Impact factor: 7.446

3 in total