Diisopropyl-ammonium methane-sulfonate.

The title molecular salt, C(6)H(16)N(+)·CH(3)SO(3) (-), has been determined at 150 K. Two diisopropyl-ammonium cations (dipH) and two anions form N-H⋯O hydrogen-bonded cyclic dimers lying around centers of symmetry. Only two of the three O atoms of the methane-sulfonate anion are involved in hydrogen bonding, resulting in slightly longer S-O bond lengths. The title structure represents an example of a sulfonate anion that is part of a hydrogen-bonding R(4) (4)(12) graph-set motif, which is well known for related dipH acetates. Additionally, the Raman and the IR spectroscopic data for the title compound are presented.

Related literature

For simple dipH salts, see: Bajorat & Reiss (2007 ▶); Reiss (1998 ▶, 2002 ▶); Reiss (2010a ▶,b ▶); Reiss & Engel (2004 ▶); Reiss & Meyer (2010 ▶); Sada et al. (2004 ▶), Summers et al. (1998 ▶). For spectroscopic data for sulfonate salts, see: Thomson (1972 ▶); Genceli Guner et al. (2010 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H16N+·CH3SO3 −

M = 197.29

Monoclinic,

a = 8.88154 (13) Å

b = 8.53537 (13) Å

c = 14.5784 (2) Å

β = 101.8161 (15)°

V = 1081.73 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 150 K

0.65 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.951, T max = 1.000

25064 measured reflections

3149 independent reflections

2782 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.060

S = 1.03

3149 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029382/qm2018sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029382/qm2018Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029382/qm2018Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811029382/qm2018Isup4.cml

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

C6H16N+·CH3SO3−	F(000) = 432
Mr = 197.29	Dx = 1.211 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18202 reflections
a = 8.88154 (13) Å	θ = 3.4–32.0°
b = 8.53537 (13) Å	µ = 0.27 mm−1
c = 14.5784 (2) Å	T = 150 K
β = 101.8161 (15)°	Needle, colourless
V = 1081.73 (3) Å3	0.65 × 0.25 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2782 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 16.27 pixels mm-1	θmax = 30.0°, θmin = 4.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.951, Tmax = 1.000	l = −20→20
25064 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.01P)2 + 0.55P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3149 reflections	Δρmax = 0.34 e Å−3
146 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0276 (9)

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52, Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK.

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
S1	0.38147 (3)	0.02594 (3)	0.180331 (16)	0.01976 (7)
O1	0.47025 (9)	0.13813 (10)	0.13749 (6)	0.0355 (2)
O2	0.47472 (10)	−0.09928 (12)	0.22849 (6)	0.0408 (2)
O3	0.24712 (9)	−0.03058 (10)	0.11340 (5)	0.02989 (17)
C1	0.30699 (15)	0.12931 (19)	0.26524 (9)	0.0442 (3)
H1A	0.2477	0.0595	0.2955	0.065 (5)*
H1B	0.2424	0.2128	0.2357	0.062 (5)*
H1C	0.3901	0.1721	0.3109	0.066 (5)*
N1	0.74609 (9)	0.09843 (10)	0.07323 (6)	0.01840 (16)
H11	0.6562 (15)	0.0976 (15)	0.0906 (9)	0.028 (3)*
H12	0.7329 (14)	0.0729 (15)	0.0128 (9)	0.028 (3)*
C2	0.84677 (11)	−0.02552 (12)	0.12848 (7)	0.02104 (18)
H2	0.9413 (14)	−0.0236 (14)	0.1056 (8)	0.022 (3)*
C3	0.76690 (13)	−0.18212 (12)	0.10422 (8)	0.0283 (2)
H3A	0.6709	−0.1827	0.1248	0.036 (4)*
H3B	0.8313	−0.2649	0.1349	0.039 (4)*
H3C	0.7480	−0.1977	0.0376	0.037 (4)*
C4	0.87442 (13)	0.00990 (14)	0.23269 (7)	0.0286 (2)
H4A	0.9296	0.1069	0.2452	0.036 (4)*
H4B	0.9337	−0.0731	0.2670	0.037 (4)*
H4C	0.7775	0.0183	0.2517	0.037 (4)*
C5	0.80229 (12)	0.26542 (12)	0.08130 (7)	0.02175 (19)
H5	0.8146 (13)	0.2921 (14)	0.1445 (8)	0.022 (3)*
C6	0.67707 (14)	0.36632 (13)	0.02325 (8)	0.0322 (2)
H6A	0.6606	0.3347	−0.0412	0.041 (4)*
H6B	0.7081	0.4742	0.0286	0.049 (4)*
H6C	0.5834	0.3538	0.0457	0.041 (4)*
C7	0.95364 (13)	0.27936 (14)	0.04905 (8)	0.0296 (2)
H7A	1.0290	0.2129	0.0868	0.041 (4)*
H7B	0.9884	0.3861	0.0553	0.042 (4)*
H7C	0.9393	0.2479	−0.0154	0.036 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01698 (10)	0.02503 (12)	0.01773 (10)	0.00188 (9)	0.00463 (8)	−0.00071 (9)
O1	0.0289 (4)	0.0331 (4)	0.0485 (5)	−0.0013 (3)	0.0171 (4)	0.0074 (4)
O2	0.0310 (4)	0.0471 (5)	0.0445 (5)	0.0131 (4)	0.0083 (4)	0.0205 (4)
O3	0.0267 (4)	0.0403 (4)	0.0216 (3)	−0.0034 (3)	0.0022 (3)	−0.0084 (3)
C1	0.0305 (6)	0.0663 (9)	0.0370 (6)	−0.0021 (6)	0.0101 (5)	−0.0286 (7)
N1	0.0188 (4)	0.0194 (4)	0.0171 (4)	−0.0008 (3)	0.0040 (3)	−0.0005 (3)
C2	0.0193 (4)	0.0209 (4)	0.0238 (4)	0.0026 (4)	0.0064 (3)	0.0024 (4)
C3	0.0306 (5)	0.0205 (5)	0.0350 (6)	−0.0003 (4)	0.0096 (4)	0.0007 (4)
C4	0.0295 (5)	0.0322 (6)	0.0223 (5)	0.0020 (4)	0.0009 (4)	0.0043 (4)
C5	0.0269 (5)	0.0187 (4)	0.0196 (4)	−0.0025 (4)	0.0045 (4)	−0.0015 (3)
C6	0.0368 (6)	0.0235 (5)	0.0360 (6)	0.0049 (4)	0.0067 (5)	0.0058 (4)
C7	0.0278 (5)	0.0295 (6)	0.0317 (5)	−0.0080 (4)	0.0066 (4)	0.0030 (4)

S1—O2	1.4433 (9)	C3—H3B	0.9600
S1—O1	1.4596 (8)	C3—H3C	0.9600
S1—O3	1.4600 (8)	C4—H4A	0.9600
S1—C1	1.7560 (12)	C4—H4B	0.9600
C1—H1A	0.9600	C4—H4C	0.9600
C1—H1B	0.9600	C5—C6	1.5196 (15)
C1—H1C	0.9600	C5—C7	1.5169 (14)
N1—C5	1.5068 (13)	C5—H5	0.934 (12)
N1—C2	1.5076 (12)	C6—H6A	0.9600
N1—H11	0.885 (13)	C6—H6B	0.9600
N1—H12	0.891 (13)	C6—H6C	0.9600
C2—C4	1.5189 (14)	C7—H7A	0.9600
C2—C3	1.5206 (14)	C7—H7B	0.9600
C2—H2	0.964 (12)	C7—H7C	0.9600
C3—H3A	0.9600
O2—S1—O1	112.80 (5)	N1—C2—C4	110.58 (8)
O2—S1—O3	112.92 (6)	N1—C2—C3	107.17 (8)
O1—S1—O3	111.71 (5)	C4—C2—C3	112.32 (9)
O2—S1—C1	106.90 (7)	N1—C2—H2	105.4 (7)
O1—S1—C1	106.65 (7)	C4—C2—H2	111.6 (7)
O3—S1—C1	105.24 (5)	C3—C2—H2	109.4 (7)
C5—N1—C2	118.12 (8)	N1—C5—C6	107.44 (8)
C5—N1—H11	106.8 (9)	N1—C5—C7	110.51 (8)
C2—N1—H11	108.2 (8)	C6—C5—C7	112.14 (9)
C5—N1—H12	106.4 (8)	N1—C5—H5	106.1 (8)
C2—N1—H12	107.5 (8)	C6—C5—H5	109.6 (7)
H11—N1—H12	109.6 (11)	C7—C5—H5	110.8 (7)
C5—N1—C2—C4	59.81 (11)	C2—N1—C5—C6	−177.19 (8)
C5—N1—C2—C3	−177.47 (8)	C2—N1—C5—C7	60.18 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1	0.885 (13)	1.944 (13)	2.8168 (11)	168.5 (12)
N1—H12···O3i	0.891 (13)	1.919 (13)	2.7944 (11)	166.9 (12)

Table 1

Selected geometric parameters (Å, °)

S1—O2	1.4433 (9)
S1—O1	1.4596 (8)
S1—O3	1.4600 (8)
S1—C1	1.7560 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O1	0.885 (13)	1.944 (13)	2.8168 (11)	168.5 (12)
N1—H12⋯O3i	0.891 (13)	1.919 (13)	2.7944 (11)	166.9 (12)

Symmetry code: (i) .