1-Methyl-1-propyl-pyrrolidinium chloride.

The aymmetric unit of the title compound, C(8)H(18)N(+)·Cl(-), consists of one crystallographically independent 1-methyl-1-propyl-pyrrolidinium cation and one chloride anion, both of which lie in general positions. Minor hydrogen-bonded C-H⋯Cl inter-actions occur. However, no classical hydrogen bonding is observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For comparative thermal and crystallographic analysis of four crystallized N-alkyl-N-methyl­pyrrolidinium and piperidinium bis­(trifluoro­methane­sulfon­yl)imide salts and an insight into why these salts form room-temperature ionic liquids, see: Henderson et al. (2006 ▶). For the synthesis and analysis of N-butyl-N-methyl pyrrolidinium chloride, an analogue of the title compound, see: Lancaster et al. (2002 ▶). For the first synthesis and analysis of the new pyrrolidinium family of molten salts, see: MacFarlane et al. (1999 ▶). For the quanti­tative comparison of inter­molecular inter­actions using Hirshfeld surfaces, see: McKinnon et al. (2007 ▶). For the first synthesis and analysis of 1-alkyl-2-methyl pyrrolidinium ionic liquids involving the bis­(trifluoro­methane­sulfon­yl)imide anion, see: Sun et al. (2003 ▶).

Experimental

Crystal data

C8H18N+·Cl−

M = 163.68

Orthorhombic,

a = 14.5863 (5) Å

b = 13.2196 (4) Å

c = 9.9779 (3) Å

V = 1923.99 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 123 (2) K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.907, T max = 0.907

11550 measured reflections

1982 independent reflections

1800 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.04

1982 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: POV-RAY (Persistence of Vision, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005229/zl2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005229/zl2101Isup2.hkl

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

C8H18N+·Cl–	Dx = 1.130 Mg m−3
Mr = 163.68	Melting point: 323.5 K
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4825 reflections
a = 14.5863 (5) Å	θ = 2.8–26.4º
b = 13.2196 (4) Å	µ = 0.33 mm−1
c = 9.9779 (3) Å	T = 123 (2) K
V = 1923.99 (11) Å3	Cubic, colourless
Z = 8	0.30 × 0.30 × 0.30 mm
F000 = 720

Bruker X8 APEX KappaCCD diffractometer	1982 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 123(2) K	θmax = 26.4º
0.5° frames in φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −18→18
Tmin = 0.907, Tmax = 0.907	k = −15→16
11550 measured reflections	l = −11→12

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.834P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
1982 reflections	Δρmax = 0.25 e Å−3
93 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Uiso*/Ueq
Cl1	0.36024 (2)	0.82436 (2)	0.05218 (3)	0.02423 (12)
N1	0.32912 (7)	0.86923 (8)	0.43497 (10)	0.0179 (2)
C1	0.35707 (9)	0.75928 (10)	0.41992 (14)	0.0241 (3)
H1A	0.3939	0.7496	0.3376	0.029*
H1B	0.3023	0.7152	0.4152	0.029*
C2	0.41390 (11)	0.73488 (12)	0.54424 (15)	0.0323 (3)
H2A	0.4793	0.7268	0.5202	0.039*
H2B	0.3922	0.6714	0.5863	0.039*
C3	0.40131 (10)	0.82444 (12)	0.64053 (15)	0.0309 (3)
H3A	0.3884	0.8004	0.7326	0.037*
H3B	0.4569	0.8674	0.6423	0.037*
C4	0.32014 (9)	0.88251 (11)	0.58455 (13)	0.0242 (3)
H4A	0.2616	0.8540	0.6174	0.029*
H4B	0.3234	0.9549	0.6097	0.029*
C5	0.40372 (8)	0.93610 (10)	0.38042 (13)	0.0209 (3)
H5A	0.4045	0.9315	0.2824	0.031*
H5B	0.4631	0.9141	0.4161	0.031*
H5C	0.3922	1.0063	0.4072	0.031*
C6	0.23958 (8)	0.88722 (10)	0.36358 (13)	0.0198 (3)
H6A	0.1941	0.8374	0.3962	0.024*
H6B	0.2487	0.8750	0.2666	0.024*
C7	0.20062 (9)	0.99281 (11)	0.38223 (14)	0.0254 (3)
H7A	0.1931	1.0073	0.4789	0.031*
H7B	0.2433	1.0434	0.3442	0.031*
C8	0.10858 (10)	0.99984 (12)	0.31221 (18)	0.0372 (4)
H8A	0.1173	0.9926	0.2153	0.056*
H8B	0.0806	1.0657	0.3313	0.056*
H8C	0.0683	0.9458	0.3447	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.02343 (18)	0.02619 (19)	0.02308 (18)	−0.00399 (13)	−0.00151 (13)	−0.00178 (12)
N1	0.0162 (5)	0.0191 (5)	0.0185 (5)	−0.0015 (4)	−0.0013 (4)	0.0004 (4)
C1	0.0246 (7)	0.0178 (6)	0.0299 (7)	0.0005 (5)	−0.0008 (6)	0.0012 (5)
C2	0.0282 (7)	0.0287 (8)	0.0401 (9)	0.0006 (6)	−0.0051 (6)	0.0123 (6)
C3	0.0273 (7)	0.0406 (9)	0.0247 (7)	−0.0068 (6)	−0.0067 (6)	0.0100 (6)
C4	0.0232 (6)	0.0322 (8)	0.0172 (6)	−0.0044 (6)	−0.0004 (5)	−0.0005 (5)
C5	0.0163 (6)	0.0223 (7)	0.0241 (6)	−0.0031 (5)	0.0008 (5)	0.0023 (5)
C6	0.0157 (6)	0.0231 (6)	0.0206 (6)	−0.0019 (5)	−0.0035 (5)	−0.0014 (5)
C7	0.0208 (6)	0.0257 (7)	0.0298 (7)	0.0018 (5)	−0.0037 (6)	−0.0049 (6)
C8	0.0258 (7)	0.0314 (8)	0.0543 (10)	0.0050 (6)	−0.0138 (7)	−0.0065 (7)

N1—C5	1.5038 (16)	C4—H4B	0.9900
N1—C6	1.5066 (16)	C5—H5A	0.9800
N1—C4	1.5085 (16)	C5—H5B	0.9800
N1—C1	1.5171 (17)	C5—H5C	0.9800
C1—C2	1.526 (2)	C6—C7	1.5185 (18)
C1—H1A	0.9900	C6—H6A	0.9900
C1—H1B	0.9900	C6—H6B	0.9900
C2—C3	1.536 (2)	C7—C8	1.5163 (19)
C2—H2A	0.9900	C7—H7A	0.9900
C2—H2B	0.9900	C7—H7B	0.9900
C3—C4	1.518 (2)	C8—H8A	0.9800
C3—H3A	0.9900	C8—H8B	0.9800
C3—H3B	0.9900	C8—H8C	0.9800
C4—H4A	0.9900
C5—N1—C6	111.31 (10)	N1—C4—H4B	111.0
C5—N1—C4	110.64 (10)	C3—C4—H4B	111.0
C6—N1—C4	111.98 (10)	H4A—C4—H4B	109.0
C5—N1—C1	109.44 (10)	N1—C5—H5A	109.5
C6—N1—C1	109.72 (10)	N1—C5—H5B	109.5
C4—N1—C1	103.46 (10)	H5A—C5—H5B	109.5
N1—C1—C2	105.54 (11)	N1—C5—H5C	109.5
N1—C1—H1A	110.6	H5A—C5—H5C	109.5
C2—C1—H1A	110.6	H5B—C5—H5C	109.5
N1—C1—H1B	110.6	N1—C6—C7	114.30 (10)
C2—C1—H1B	110.6	N1—C6—H6A	108.7
H1A—C1—H1B	108.8	C7—C6—H6A	108.7
C1—C2—C3	106.30 (12)	N1—C6—H6B	108.7
C1—C2—H2A	110.5	C7—C6—H6B	108.7
C3—C2—H2A	110.5	H6A—C6—H6B	107.6
C1—C2—H2B	110.5	C8—C7—C6	109.34 (11)
C3—C2—H2B	110.5	C8—C7—H7A	109.8
H2A—C2—H2B	108.7	C6—C7—H7A	109.8
C4—C3—C2	104.66 (11)	C8—C7—H7B	109.8
C4—C3—H3A	110.8	C6—C7—H7B	109.8
C2—C3—H3A	110.8	H7A—C7—H7B	108.3
C4—C3—H3B	110.8	C7—C8—H8A	109.5
C2—C3—H3B	110.8	C7—C8—H8B	109.5
H3A—C3—H3B	108.9	H8A—C8—H8B	109.5
N1—C4—C3	103.74 (11)	C7—C8—H8C	109.5
N1—C4—H4A	111.0	H8A—C8—H8C	109.5
C3—C4—H4A	111.0	H8B—C8—H8C	109.5
C5—N1—C1—C2	85.97 (12)	C1—N1—C4—C3	40.98 (12)
C6—N1—C1—C2	−151.63 (11)	C2—C3—C4—N1	−33.99 (14)
C4—N1—C1—C2	−31.99 (13)	C5—N1—C6—C7	−63.82 (14)
N1—C1—C2—C3	10.96 (15)	C4—N1—C6—C7	60.62 (14)
C1—C2—C3—C4	14.09 (15)	C1—N1—C6—C7	174.90 (11)
C5—N1—C4—C3	−76.14 (13)	N1—C6—C7—C8	−177.02 (12)
C6—N1—C4—C3	159.05 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Cl1i	0.99	2.79	3.607 (1)	141
C2—H2A···Cl1ii	0.99	2.77	3.630 (2)	146
C5—H5A···Cl1	0.98	2.77	3.648 (1)	149
C5—H5C···Cl1iii	0.98	2.71	3.656 (1)	163
C6—H6A···Cl1i	0.99	2.76	3.672 (1)	153
C6—H6B···Cl1	0.99	2.77	3.666 (1)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯Cl1i	0.99	2.79	3.607 (1)	141
C2—H2A⋯Cl1ii	0.99	2.77	3.630 (2)	146
C5—H5A⋯Cl1	0.98	2.77	3.648 (1)	149
C5—H5C⋯Cl1iii	0.98	2.71	3.656 (1)	163
C6—H6A⋯Cl1i	0.99	2.76	3.672 (1)	153
C6—H6B⋯Cl1	0.99	2.77	3.666 (1)	151

Symmetry codes: (i) ; (ii) ; (iii) .