1-Methyl-1H-imidazol-3-ium methane­sulfonate

The structure of the title salt, C₄H₇N₂⁺·CH₃O₃S⁻, has monoclinic (P2₁/n) symmetry. The 1-methyl­imidazolium cation and the methyl­sulfonate anion in the asymmetric unit are held together by a strong N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 230 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.085
• Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SAINT (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Methyl-1H-imidazol-3-ium methanesulfonate

Crystal data

C4H7N2^+·CH3O3S^−	F(000) = 376
Mr = 178.21	Dx = 1.458 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.1891 (5) Å	Cell parameters from 9900 reflections
b = 7.4627 (4) Å	θ = 3.3–28.3°
c = 11.4884 (6) Å	µ = 0.36 mm^−1
β = 111.635 (1)°	T = 230 K
V = 812.02 (7) Å^3	Block, colourless
Z = 4	0.58 × 0.4 × 0.36 mm

Data collection

Bruker D8 Quest CMOS diffractometer	2011 independent reflections
Radiation source: sealed tube	1827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 10.42 pixels mm^-1	θmax = 28.4°, θmin = 3.3°
φ and ω shutterless scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −9→9
Tmin = 0.707, Tmax = 0.746	l = −15→15
11035 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0399P)^2 + 0.3268P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2011 reflections	Δρmax = 0.23 e Å^−3
102 parameters	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.67678 (3)	0.74219 (4)	0.90924 (3)	0.02711 (11)
O1	0.72814 (12)	0.64890 (15)	0.82397 (10)	0.0424 (3)
O2	0.58946 (10)	0.62642 (13)	0.95480 (8)	0.0354 (2)
O3	0.78655 (11)	0.83115 (16)	1.01095 (10)	0.0468 (3)
N1	0.38601 (11)	0.26564 (14)	0.59635 (10)	0.0283 (2)
N2	0.43894 (12)	0.37124 (16)	0.78128 (11)	0.0384 (3)
H2	0.483452	0.427925	0.850900	0.046*
C1	0.47811 (14)	0.36423 (18)	0.68438 (13)	0.0349 (3)
H1	0.558245	0.420035	0.678699	0.042*
C2	0.28337 (14)	0.2092 (2)	0.63836 (13)	0.0347 (3)
H2A	0.204560	0.137987	0.594256	0.042*
C3	0.31699 (16)	0.2752 (2)	0.75517 (14)	0.0408 (3)
H3	0.266479	0.258443	0.808246	0.049*
C4	0.38835 (18)	0.2315 (2)	0.47203 (14)	0.0456 (4)
H4A	0.362591	0.107785	0.448925	0.068*
H4B	0.482460	0.253917	0.472837	0.068*
H4C	0.321550	0.310260	0.411695	0.068*
C5	0.56302 (18)	0.9098 (3)	0.81923 (19)	0.0552 (4)
H5A	0.484569	0.854603	0.752852	0.083*
H5B	0.614304	0.987198	0.782942	0.083*
H5C	0.527445	0.980152	0.872276	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02786 (17)	0.02531 (17)	0.02782 (17)	−0.00194 (10)	0.00987 (13)	0.00137 (11)
O1	0.0502 (6)	0.0444 (6)	0.0383 (5)	0.0050 (5)	0.0228 (5)	−0.0008 (4)
O2	0.0419 (5)	0.0357 (5)	0.0285 (4)	−0.0136 (4)	0.0128 (4)	−0.0001 (4)
O3	0.0407 (6)	0.0527 (7)	0.0441 (6)	−0.0190 (5)	0.0121 (5)	−0.0124 (5)
N1	0.0306 (5)	0.0254 (5)	0.0270 (5)	−0.0018 (4)	0.0083 (4)	−0.0002 (4)
N2	0.0388 (6)	0.0354 (6)	0.0303 (5)	0.0046 (5)	0.0003 (5)	−0.0091 (5)
C1	0.0307 (6)	0.0276 (6)	0.0396 (7)	−0.0027 (5)	0.0051 (5)	−0.0006 (5)
C2	0.0318 (6)	0.0393 (7)	0.0323 (7)	−0.0074 (5)	0.0109 (5)	−0.0032 (6)
C3	0.0397 (7)	0.0510 (9)	0.0325 (7)	0.0027 (6)	0.0142 (6)	−0.0034 (6)
C4	0.0545 (9)	0.0541 (9)	0.0333 (7)	−0.0080 (7)	0.0220 (7)	−0.0044 (6)
C5	0.0492 (9)	0.0469 (9)	0.0735 (11)	0.0159 (7)	0.0271 (8)	0.0264 (9)

Geometric parameters (Å, º)

S1—O1	1.4478 (10)	C1—H1	0.9400
S1—O2	1.4680 (9)	C2—H2A	0.9400
S1—O3	1.4468 (10)	C2—C3	1.350 (2)
S1—C5	1.7590 (16)	C3—H3	0.9400
N1—C1	1.3210 (17)	C4—H4A	0.9700
N1—C2	1.3699 (17)	C4—H4B	0.9700
N1—C4	1.4596 (17)	C4—H4C	0.9700
N2—H2	0.8700	C5—H5A	0.9700
N2—C1	1.3149 (19)	C5—H5B	0.9700
N2—C3	1.369 (2)	C5—H5C	0.9700
O1—S1—O2	112.08 (6)	C3—C2—H2A	126.5
O1—S1—C5	105.57 (8)	N2—C3—H3	126.7
O2—S1—C5	105.88 (7)	C2—C3—N2	106.63 (13)
O3—S1—O1	113.73 (7)	C2—C3—H3	126.7
O3—S1—O2	111.83 (6)	N1—C4—H4A	109.5
O3—S1—C5	107.10 (9)	N1—C4—H4B	109.5
C1—N1—C2	108.71 (11)	N1—C4—H4C	109.5
C1—N1—C4	125.66 (12)	H4A—C4—H4B	109.5
C2—N1—C4	125.53 (12)	H4A—C4—H4C	109.5
C1—N2—H2	125.4	H4B—C4—H4C	109.5
C1—N2—C3	109.15 (12)	S1—C5—H5A	109.5
C3—N2—H2	125.4	S1—C5—H5B	109.5
N1—C1—H1	125.7	S1—C5—H5C	109.5
N2—C1—N1	108.58 (12)	H5A—C5—H5B	109.5
N2—C1—H1	125.7	H5A—C5—H5C	109.5
N1—C2—H2A	126.5	H5B—C5—H5C	109.5
C3—C2—N1	106.92 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.87	1.96	2.775 (2)	156