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

In the organic cation of the title compound, C(13)H(20)N(3) (+)·Cl(-)·H(2)O, 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 inter-molecular O-H⋯Cl hydrogen bonds link the water mol-ecules and chloride anions into an R(4) (4)(8) ring motif. Inter-molecular N-H⋯Cl, C-H⋯Cl and C-H⋯O hydrogen bonds further inter-connect 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 = 271.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.129

S = 1.26

5073 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.47 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H20N3+·Cl−·H2O	F(000) = 584
Mr = 271.79	Dx = 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

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

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(Fo2) + (0.0709P)2 + 0.155P] where P = (Fo2 + 2Fc2)/3
5073 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .