2,6-Di(pyrrolidin-1-yl)pyridinium chloride monohydrate

Al-Dajani, M.T.M.; Abdallah, H.H.; Mohamed, N.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S160053681002427X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1815-o1816

doi:10.1107/S160053681002427X

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2,6-Di(pyrrolidin-1-yl)pyridinium chloride monohydrate

Mohammad T. M. Al-Dajani,^a Hassan H. Abdallah,^b Nornisah Mohamed,^a ‡ Jia Hao Goh ^c § and Hoong-Kun Fun ^c ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 15 June 2010; accepted 22 June 2010; online 26 June 2010)

In the organic cation of the title compound, C₁₃H₂₀N₃⁺·Cl⁻·H₂O, the two pyrrolidine rings adopt twisted conformations. The pyridine ring makes dihedral angles of 14.57 (6) and 23.96 (6)° with the mean planes of the pyrrolidine rings. In the crystal structure, pairs of bifurcated intermolecular O—H⋯Cl hydrogen bonds link the water molecules and chloride anions into an R₄⁴(8) ring motif. Intermolecular N—H⋯Cl, C—H⋯Cl and C—H⋯O hydrogen bonds further interconnect these rings with the organic cations into a two-dimensional network parallel to the bc plane.

Related literature

For general background to and applications of the title compound, see: Cornell et al. (2003 ); Fetzner (1998 ); Padoley et al. (2008 ); Xue & Warshawsky (2005 ); Zhu et al. (2003 ). For puckering analysis and ring conformations, see: Cremer & Pople (1975 ). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ). For reference bond-length data, see: Allen et al. (1987 ). For related structures, see: Al-Dajani et al. (2009 ); Rubin-Preminger & Englert (2007 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₂₀N₃⁺·Cl⁻·H₂O
M_r = 271.79
Monoclinic, P 2₁ /c
a = 11.5728 (15) Å
b = 12.2724 (16) Å
c = 11.3622 (16) Å
β = 119.214 (2)°
V = 1408.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.36 × 0.25 × 0.21 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.911, T_max = 0.947
20960 measured reflections
5073 independent reflections
4506 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.129
S = 1.26
5073 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯Cl1	0.84	2.45	3.2246 (10)	153
O1W—H1W1⋯Cl1	0.91	2.35	3.2502 (11)	169
O1W—H2W1⋯Cl1ⁱ	0.82	2.45	3.2594 (11)	171
C1—H1B⋯Cl1	0.97	2.76	3.5100 (11)	135
C7—H7A⋯O1Wⁱⁱ	0.93	2.35	3.2122 (15)	154
C13—H13A⋯Cl1	0.97	2.78	3.5555 (13)	138
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002427X/is2565sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002427X/is2565Isup2.hkl

checkCIF report

Comment top

Nitrogen heterocyclic compounds have received a lot of attention especially by the environment scientists. The main sources of these compounds in the environment are the coal gasification, shale oil extraction and pesticide production (Zhu et al., 2003; Fetzner, 1998). The metabolic activation of the heterocyclic compounds and the DNA damage produced (Xue & Warshawsky, 2005) as well as their roles as a pollutants (Padoley et al., 2008) and their deposition on land and coastal environments (Cornell et al., 2003) have been reported. The title compound can be used for the synthesis of new organometallic complexes and in the field of biological activity and drug design.

The asymmetric unit of the title salt comprises of a protonated 2,6-di(pyrrolidin-1-yl)pyridinium cation, a chloride anion and a water molecule (Fig. 1). In the organic cation, the two pyrrolidine rings adopts twisted conformations (Cremer & Pople, 1975). The puckering parameters are Q = 0.3969 (12) Å, ϕ = 94.02 (16)° for C1-C4/N1; and Q = 0.3732 (13) Å, ϕ = 274.73 (17)° for C10-C13/N3. The essentially planar pyridine ring (C5-C9/N2) makes dihedral angles of 23.96 (6) and 14.57 (6)°, respectively, with the mean planes formed through the C1-C4/N1 and C10-C13/N3 pyrrolidine rings. Comparing to the unprotonated structure (Rubin-Preminger & Englert, 2007), protonation at atom N2 has lead to a slight increase in the C5—N2—C9 angle to 122.97 (8)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a related pyridine structure (Al-Dajani et al., 2009).

In the crystal structure (Fig. 2), the chloride anions provide the most extensive part as hydrogen bond acceptors. Pairs of intermolecular O1W—H1W1···Cl1 and O1W—H2W1···Cl1 bifurcated hydrogen bonds (Table 1) link the chloride anions and water molecules into R⁴₄(8) ring motifs (Bernstein et al., 1995) in a DAAD manner. These ring motifs are further interconnected with the organic cations into two-dimensional arrays parallel to the bc plane via intermolecular N2—H1N2···Cl1, C1—H1B···Cl1, C7—H7A···O1W and C13—H13A···Cl1 hydrogen bonds (Table 1).

Related literature top

For general background to and applications of the title compound, see: Cornell et al. (2003); Fetzner (1998); Padoley et al. (2008); Xue & Warshawsky (2005); Zhu et al. (2003). For puckering analysis and ring conformations, see: Cremer & Pople (1975). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For reference bond-length data, see: Allen et al. (1987). For related structures, see: Al-Dajani et al. (2009); Rubin-Preminger & Englert (2007). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

In a two-neck round bottom flask, pyridine (0.01 mol, 1.0 g) was dissolved in THF (50 ml). The flask was connected to dropping funnel containing anhydrous aluminum chloride (2.7 g, 0.02 mol) dissolved in THF (25 ml) and ended with anhydrous calcium chloride drying tube. In an ice bath, the aluminum chloride solution was added in small portions and the temperature was maintained between 273–278 K during the addition. The mixture was refluxed for 30 mins at 323–328 K under dry condition. Pyrrolidine (0.02 mol, 1.5 g) was added in small portions to the formed red colour reaction mixture. After stirring for 1 h, the mixture was decanted on ice water and the organic layer was extracted with butanol. The solvent was evaporated by using the rotary evaporator. Deep brown single crystals were formed after one week at room temperature and washed with methanol and dried at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title salt, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal structure of the title salt, viewed along the a axis, showing a two-dimensional array parallel to the bc plane. H atoms not involved in intermolecular hydrogen bonds (dashed lines) have been omitted for clarity.

2,6-Di(pyrrolidin-1-yl)pyridinium chloride monohydrate top

Crystal data top

C₁₃H₂₀N₃⁺·Cl⁻·H₂O	F(000) = 584
M_r = 271.79	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9025 reflections
a = 11.5728 (15) Å	θ = 3.6–35.1°
b = 12.2724 (16) Å	µ = 0.27 mm⁻¹
c = 11.3622 (16) Å	T = 100 K
β = 119.214 (2)°	Block, brown
V = 1408.5 (3) Å³	0.36 × 0.25 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5073 independent reflections
Radiation source: fine-focus sealed tube	4506 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 32.5°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.911, T_max = 0.947	k = −18→18
20960 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.26	w = 1/[σ²(F_o²) + (0.0709P)² + 0.155P] where P = (F_o² + 2F_c²)/3
5073 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₃H₂₀N₃⁺·Cl⁻·H₂O	V = 1408.5 (3) Å³
M_r = 271.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5728 (15) Å	µ = 0.27 mm⁻¹
b = 12.2724 (16) Å	T = 100 K
c = 11.3622 (16) Å	0.36 × 0.25 × 0.21 mm
β = 119.214 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5073 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4506 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.947	R_int = 0.028
20960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.26	Δρ_max = 0.85 e Å⁻³
5073 reflections	Δρ_min = −0.47 e Å⁻³
163 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.19322 (2)	0.62909 (2)	0.66837 (2)	0.01949 (8)
N1	0.36262 (7)	0.57142 (7)	1.04747 (8)	0.01531 (15)
N2	0.14198 (7)	0.52984 (6)	0.90169 (8)	0.01275 (14)
H1N2	0.1409	0.5734	0.8446	0.015*
N3	−0.08202 (7)	0.50501 (7)	0.75519 (8)	0.01540 (15)
C1	0.34608 (9)	0.68840 (8)	1.01429 (10)	0.01729 (17)
H1A	0.2653	0.7163	1.0090	0.021*
H1B	0.3446	0.7022	0.9295	0.021*
C2	0.46810 (9)	0.73903 (9)	1.13225 (11)	0.0226 (2)
H2A	0.4514	0.7568	1.2058	0.027*
H2B	0.4954	0.8045	1.1045	0.027*
C3	0.57226 (10)	0.64951 (9)	1.17295 (12)	0.0231 (2)
H3A	0.6087	0.6468	1.1121	0.028*
H3B	0.6437	0.6601	1.2644	0.028*
C4	0.49368 (9)	0.54686 (9)	1.16178 (10)	0.02016 (19)
H4A	0.5325	0.4835	1.1435	0.024*
H4B	0.4888	0.5344	1.2436	0.024*
C5	0.26136 (9)	0.50134 (7)	1.01015 (9)	0.01296 (16)
C6	0.27123 (9)	0.40293 (8)	1.07522 (10)	0.01685 (17)
H6A	0.3516	0.3802	1.1467	0.020*
C7	0.15781 (10)	0.33922 (8)	1.03070 (10)	0.01769 (18)
H7A	0.1637	0.2735	1.0740	0.021*
C8	0.03737 (10)	0.36996 (7)	0.92503 (10)	0.01668 (18)
H8A	−0.0372	0.3266	0.8984	0.020*
C9	0.02951 (8)	0.46816 (7)	0.85822 (9)	0.01324 (16)
C10	−0.20146 (9)	0.43731 (9)	0.69091 (11)	0.02049 (19)
H10A	−0.2389	0.4269	0.7501	0.025*
H10B	−0.1827	0.3667	0.6657	0.025*
C11	−0.29411 (10)	0.50344 (10)	0.56689 (11)	0.0251 (2)
H11A	−0.3857	0.4926	0.5440	0.030*
H11B	−0.2836	0.4836	0.4900	0.030*
C12	−0.25148 (10)	0.62099 (9)	0.60917 (11)	0.0217 (2)
H12A	−0.2777	0.6675	0.5312	0.026*
H12B	−0.2893	0.6492	0.6627	0.026*
C13	−0.10123 (9)	0.61292 (8)	0.69258 (10)	0.01769 (18)
H13A	−0.0603	0.6171	0.6359	0.021*
H13B	−0.0654	0.6700	0.7601	0.021*
O1W	0.07681 (10)	0.38244 (7)	0.62242 (9)	0.02792 (19)
H1W1	0.0986	0.4542	0.6261	0.042*
H2W1	0.0048	0.3828	0.5536	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01614 (12)	0.02374 (14)	0.01981 (13)	0.00041 (7)	0.00973 (10)	0.00133 (8)
N1	0.0105 (3)	0.0137 (3)	0.0163 (3)	−0.0004 (2)	0.0023 (3)	0.0012 (3)
N2	0.0111 (3)	0.0121 (3)	0.0131 (3)	−0.0003 (2)	0.0044 (3)	0.0008 (2)
N3	0.0101 (3)	0.0150 (3)	0.0172 (3)	−0.0008 (2)	0.0036 (3)	−0.0021 (3)
C1	0.0140 (4)	0.0132 (4)	0.0203 (4)	−0.0011 (3)	0.0050 (3)	−0.0005 (3)
C2	0.0140 (4)	0.0192 (4)	0.0281 (5)	−0.0034 (3)	0.0054 (4)	−0.0073 (4)
C3	0.0116 (4)	0.0236 (5)	0.0275 (5)	−0.0019 (3)	0.0045 (4)	−0.0028 (4)
C4	0.0111 (4)	0.0231 (5)	0.0189 (4)	0.0012 (3)	0.0016 (3)	0.0022 (3)
C5	0.0115 (3)	0.0134 (4)	0.0129 (4)	0.0006 (3)	0.0051 (3)	−0.0003 (3)
C6	0.0167 (4)	0.0154 (4)	0.0165 (4)	0.0017 (3)	0.0066 (3)	0.0032 (3)
C7	0.0207 (4)	0.0133 (4)	0.0207 (4)	0.0007 (3)	0.0114 (3)	0.0023 (3)
C8	0.0171 (4)	0.0133 (4)	0.0208 (4)	−0.0020 (3)	0.0101 (3)	−0.0009 (3)
C9	0.0116 (3)	0.0128 (4)	0.0150 (4)	−0.0011 (3)	0.0063 (3)	−0.0031 (3)
C10	0.0126 (4)	0.0214 (4)	0.0242 (5)	−0.0043 (3)	0.0063 (3)	−0.0079 (4)
C11	0.0119 (4)	0.0369 (6)	0.0209 (5)	−0.0010 (4)	0.0037 (3)	−0.0053 (4)
C12	0.0125 (4)	0.0310 (5)	0.0200 (5)	0.0052 (3)	0.0066 (3)	0.0054 (4)
C13	0.0124 (4)	0.0204 (4)	0.0189 (4)	0.0022 (3)	0.0066 (3)	0.0034 (3)
O1W	0.0333 (4)	0.0220 (4)	0.0218 (4)	0.0079 (3)	0.0082 (3)	−0.0016 (3)

Geometric parameters (Å, º) top

N1—C5	1.3444 (11)	C5—C6	1.3914 (13)
N1—C4	1.4681 (12)	C6—C7	1.3935 (14)
N1—C1	1.4729 (13)	C6—H6A	0.9300
N2—C9	1.3724 (11)	C7—C8	1.3759 (14)
N2—C5	1.3740 (11)	C7—H7A	0.9300
N2—H1N2	0.8360	C8—C9	1.4034 (13)
N3—C9	1.3289 (11)	C8—H8A	0.9300
N3—C10	1.4659 (12)	C10—C11	1.5229 (16)
N3—C13	1.4680 (13)	C10—H10A	0.9700
C1—C2	1.5261 (13)	C10—H10B	0.9700
C1—H1A	0.9700	C11—C12	1.5244 (17)
C1—H1B	0.9700	C11—H11A	0.9700
C2—C3	1.5263 (15)	C11—H11B	0.9700
C2—H2A	0.9700	C12—C13	1.5241 (14)
C2—H2B	0.9700	C12—H12A	0.9700
C3—C4	1.5223 (15)	C12—H12B	0.9700
C3—H3A	0.9700	C13—H13A	0.9700
C3—H3B	0.9700	C13—H13B	0.9700
C4—H4A	0.9700	O1W—H1W1	0.9117
C4—H4B	0.9700	O1W—H2W1	0.8189

C5—N1—C4	120.85 (8)	C5—C6—H6A	120.8
C5—N1—C1	123.94 (7)	C7—C6—H6A	120.8
C4—N1—C1	112.06 (7)	C8—C7—C6	122.44 (9)
C9—N2—C5	122.97 (8)	C8—C7—H7A	118.8
C9—N2—H1N2	114.9	C6—C7—H7A	118.8
C5—N2—H1N2	119.1	C7—C8—C9	118.56 (9)
C9—N3—C10	121.35 (8)	C7—C8—H8A	120.7
C9—N3—C13	125.88 (8)	C9—C8—H8A	120.7
C10—N3—C13	112.77 (8)	N3—C9—N2	118.17 (8)
N1—C1—C2	102.89 (8)	N3—C9—C8	123.19 (8)
N1—C1—H1A	111.2	N2—C9—C8	118.64 (8)
C2—C1—H1A	111.2	N3—C10—C11	103.05 (9)
N1—C1—H1B	111.2	N3—C10—H10A	111.2
C2—C1—H1B	111.2	C11—C10—H10A	111.2
H1A—C1—H1B	109.1	N3—C10—H10B	111.2
C1—C2—C3	103.21 (8)	C11—C10—H10B	111.2
C1—C2—H2A	111.1	H10A—C10—H10B	109.1
C3—C2—H2A	111.1	C10—C11—C12	103.85 (8)
C1—C2—H2B	111.1	C10—C11—H11A	111.0
C3—C2—H2B	111.1	C12—C11—H11A	111.0
H2A—C2—H2B	109.1	C10—C11—H11B	111.0
C4—C3—C2	102.66 (8)	C12—C11—H11B	111.0
C4—C3—H3A	111.2	H11A—C11—H11B	109.0
C2—C3—H3A	111.2	C13—C12—C11	103.30 (8)
C4—C3—H3B	111.2	C13—C12—H12A	111.1
C2—C3—H3B	111.2	C11—C12—H12A	111.1
H3A—C3—H3B	109.1	C13—C12—H12B	111.1
N1—C4—C3	102.77 (8)	C11—C12—H12B	111.1
N1—C4—H4A	111.2	H12A—C12—H12B	109.1
C3—C4—H4A	111.2	N3—C13—C12	102.53 (8)
N1—C4—H4B	111.2	N3—C13—H13A	111.3
C3—C4—H4B	111.2	C12—C13—H13A	111.3
H4A—C4—H4B	109.1	N3—C13—H13B	111.3
N1—C5—N2	117.40 (8)	C12—C13—H13B	111.3
N1—C5—C6	123.70 (8)	H13A—C13—H13B	109.2
N2—C5—C6	118.90 (8)	H1W1—O1W—H2W1	99.6
C5—C6—C7	118.41 (9)

C5—N1—C1—C2	150.43 (9)	C6—C7—C8—C9	1.27 (15)
C4—N1—C1—C2	−9.59 (11)	C10—N3—C9—N2	171.36 (8)
N1—C1—C2—C3	30.83 (11)	C13—N3—C9—N2	−8.05 (14)
C1—C2—C3—C4	−40.78 (11)	C10—N3—C9—C8	−9.15 (14)
C5—N1—C4—C3	−176.31 (9)	C13—N3—C9—C8	171.44 (9)
C1—N1—C4—C3	−15.59 (11)	C5—N2—C9—N3	177.66 (8)
C2—C3—C4—N1	34.27 (11)	C5—N2—C9—C8	−1.85 (13)
C4—N1—C5—N2	−179.62 (8)	C7—C8—C9—N3	−179.98 (9)
C1—N1—C5—N2	22.02 (13)	C7—C8—C9—N2	−0.49 (14)
C4—N1—C5—C6	0.56 (14)	C9—N3—C10—C11	−170.91 (9)
C1—N1—C5—C6	−157.79 (9)	C13—N3—C10—C11	8.57 (11)
C9—N2—C5—N1	−176.46 (8)	N3—C10—C11—C12	−28.80 (10)
C9—N2—C5—C6	3.37 (13)	C10—C11—C12—C13	38.50 (11)
N1—C5—C6—C7	177.33 (9)	C9—N3—C13—C12	−165.45 (9)
N2—C5—C6—C7	−2.48 (14)	C10—N3—C13—C12	15.10 (11)
C5—C6—C7—C8	0.23 (15)	C11—C12—C13—N3	−32.44 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1	0.84	2.45	3.2246 (10)	153
O1W—H1W1···Cl1	0.91	2.35	3.2502 (11)	169
O1W—H2W1···Cl1ⁱ	0.82	2.45	3.2594 (11)	171
C1—H1B···Cl1	0.97	2.76	3.5100 (11)	135
C7—H7A···O1Wⁱⁱ	0.93	2.35	3.2122 (15)	154
C13—H13A···Cl1	0.97	2.78	3.5555 (13)	138

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

Experimental details

Crystal data
Chemical formula	C₁₃H₂₀N₃⁺·Cl⁻·H₂O
M_r	271.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.5728 (15), 12.2724 (16), 11.3622 (16)
β (°)	119.214 (2)
V (Å³)	1408.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.36 × 0.25 × 0.21

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.911, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	20960, 5073, 4506
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.129, 1.26
No. of reflections	5073
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Cl1	0.8400	2.4500	3.2246 (10)	153.00
O1W—H1W1···Cl1	0.9100	2.3500	3.2502 (11)	169.00
O1W—H2W1···Cl1ⁱ	0.8200	2.4500	3.2594 (11)	171.00
C1—H1B···Cl1	0.9700	2.7600	3.5100 (11)	135.00
C7—H7A···O1Wⁱⁱ	0.9300	2.3500	3.2122 (15)	154.00
C13—H13A···Cl1	0.9700	2.7800	3.5555 (13)	138.00

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

Footnotes

‡Additional correspondence author, e-mail: nornisah@usm.my.

§Thomson Reuters ResearcherID: C-7576-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815025). HKF and JHG thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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