l-Me­thioninium nitrate

Pandiarajan, S.; Sridhar, B.; Rajaram, R.K.

doi:10.1107/S1600536802012461

L-Methioninium nitrate

S. Pandiarajan, B. Sridhar and R. K. Rajaram

The asymmetric unit of the title compound, C₅H₁₂NO₂S⁺·NO₃⁻, is composed of two crystallographically independent methioninium cations related by pseudosymmetry (−x, $1 \over 5$ + y, ½ − z) and two nitrate anions related by a pseudo-inversion centre at (0.50, 0.43, 0.25). In one of the residues, the straight side-chain conformation is gauche II–trans–gauche II, while in the other it is gauche II–trans–trans. In the crystal, the methioninium residues form N—H

O hydrogen-bonded molecular columns, which are interlinked by N—H

O and O—H

O hydrogen bonds involving the O atoms of the nitrate groups.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012461/ci6142sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012461/ci6142Isup2.hkl Contains datablock I

CCDC reference: 193758

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.131
Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.94
         From the CIF: _reflns_number_total               1924
         Count of symmetry unique reflns         1928
         Completeness (_total/calc)             99.79%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

(I) top

Crystal data top

C₅H₁₂NO₂S⁺·NO₃⁻	F(000) = 448
M_r = 212.23	D_x = 1.432 Mg m⁻³ D_m = 1.43 Mg m⁻³ D_m measured by flotation method in a mixture of carbon tetrachloride and xylene
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.682 (2) Å	Cell parameters from 25 reflections
b = 5.577 (2) Å	θ = 2.1–24.9°
c = 16.829 (6) Å	µ = 0.33 mm⁻¹
β = 100.92 (2)°	T = 293 K
V = 984.3 (5) Å³	Plate, colourless
Z = 4	0.5 × 0.3 × 0.2 mm

Data collection top

Enraf-Nonis sealed tube diffractometer	1671 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 24.9°, θ_min = 2.1°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (North et al.,1968)	k = 0→6
T_min = 0.892, T_max = 0.937	l = −19→19
2028 measured reflections	3 standard reflections every 60 min
1924 independent reflections	intensity decay: none

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0999P)² + 0.1845P] where P = (F_o² + 2F_c²)/3
1924 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.62 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.5810 (3)	1.2559 (6)	0.53643 (15)	0.0461 (8)
O1B	0.6904 (3)	0.9524 (7)	0.60230 (15)	0.0609 (10)
H1B	0.6670	1.0097	0.6419	0.091*
C11	0.6449 (3)	1.0795 (8)	0.5387 (2)	0.0333 (9)
C12	0.6870 (3)	0.9731 (7)	0.46482 (19)	0.0314 (8)
H12	0.6902	0.7981	0.4701	0.038*
N11	0.5911 (3)	1.0382 (7)	0.39152 (15)	0.0314 (7)
H11A	0.6150	0.9778	0.3477	0.047*
H11B	0.5857	1.1971	0.3872	0.047*
H11C	0.5154	0.9784	0.3959	0.047*
C13	0.8199 (3)	1.0654 (9)	0.4587 (2)	0.0383 (10)
H13A	0.8135	1.2329	0.4429	0.046*
H13B	0.8746	1.0554	0.5116	0.046*
C14	0.8805 (4)	0.9273 (11)	0.3986 (2)	0.0471 (10)
H14A	0.8269	0.9413	0.3454	0.057*
H14B	0.8843	0.7591	0.4134	0.057*
S11	1.03928 (10)	1.0289 (3)	0.39295 (7)	0.0563 (4)
C15	1.0035 (5)	1.2657 (14)	0.3219 (3)	0.0737 (16)
H15A	1.0814	1.3383	0.3133	0.111*
H15B	0.9523	1.3837	0.3423	0.111*
H15C	0.9576	1.2033	0.2716	0.111*
O2A	0.4231 (3)	1.0436 (6)	−0.03275 (15)	0.0445 (7)
O2B	0.3167 (3)	0.7424 (7)	−0.10198 (14)	0.0520 (8)
H2B	0.3436	0.8012	−0.1401	0.078*
C21	0.3596 (3)	0.8652 (7)	−0.0363 (2)	0.0304 (8)
C22	0.3123 (3)	0.7623 (8)	0.03592 (18)	0.0298 (8)
H22	0.3027	0.5882	0.0295	0.036*
N21	0.4065 (2)	0.8155 (6)	0.11038 (15)	0.0296 (7)
H21A	0.3791	0.7557	0.1531	0.044*
H21B	0.4159	0.9736	0.1160	0.044*
H21C	0.4811	0.7493	0.1068	0.044*
C23	0.1827 (3)	0.8742 (8)	0.0397 (2)	0.0358 (9)
H23A	0.1942	1.0446	0.0503	0.043*
H23B	0.1270	0.8559	−0.0126	0.043*
C24	0.1185 (3)	0.7650 (10)	0.1038 (2)	0.0432 (10)
H24A	0.1712	0.7882	0.1569	0.052*
H24B	0.1069	0.5942	0.0945	0.052*
S21	−0.03419 (9)	0.9082 (3)	0.09937 (7)	0.0544 (4)
C25	−0.0943 (4)	0.7376 (14)	0.1735 (3)	0.0692 (16)
H25A	−0.1773	0.7957	0.1778	0.104*
H25B	−0.0377	0.7532	0.2248	0.104*
H25C	−0.1001	0.5719	0.1577	0.104*
N1	0.6375 (3)	0.5370 (7)	0.28285 (16)	0.0337 (7)
O11	0.6309 (3)	0.7303 (6)	0.24700 (18)	0.0466 (8)
O12	0.6528 (3)	0.3424 (6)	0.24891 (18)	0.0515 (9)
O13	0.6275 (3)	0.5308 (6)	0.35584 (14)	0.0513 (8)
N2	0.3600 (3)	0.3182 (7)	0.21876 (17)	0.0356 (8)
O21	0.3602 (4)	0.1367 (7)	0.2596 (2)	0.0601 (9)
O22	0.3723 (3)	0.3060 (6)	0.14652 (14)	0.0517 (8)
O23	0.3505 (3)	0.5230 (6)	0.24819 (15)	0.0421 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0506 (16)	0.0516 (19)	0.0386 (13)	0.0151 (16)	0.0148 (12)	−0.0037 (14)
O1B	0.079 (2)	0.081 (3)	0.0262 (13)	0.034 (2)	0.0176 (13)	0.0089 (16)
C11	0.0274 (19)	0.044 (3)	0.0293 (17)	−0.0024 (17)	0.0068 (14)	−0.0009 (15)
C12	0.0303 (17)	0.039 (2)	0.0249 (15)	0.0016 (16)	0.0057 (13)	0.0016 (14)
N11	0.0296 (15)	0.0377 (16)	0.0270 (13)	−0.0004 (14)	0.0057 (11)	−0.0008 (14)
C13	0.0291 (18)	0.053 (3)	0.0316 (16)	−0.0025 (19)	0.0038 (14)	−0.0099 (18)
C14	0.0337 (19)	0.065 (3)	0.045 (2)	−0.006 (2)	0.0147 (16)	−0.010 (2)
S11	0.0303 (5)	0.0848 (9)	0.0549 (6)	0.0002 (6)	0.0108 (4)	0.0084 (7)
C15	0.064 (3)	0.084 (4)	0.073 (3)	−0.015 (3)	0.011 (2)	0.008 (4)
O2A	0.0458 (16)	0.0514 (18)	0.0394 (13)	−0.0125 (15)	0.0162 (12)	0.0045 (14)
O2B	0.0651 (18)	0.068 (2)	0.0260 (12)	−0.0221 (18)	0.0158 (12)	−0.0017 (15)
C21	0.0275 (18)	0.037 (2)	0.0287 (17)	−0.0005 (15)	0.0092 (14)	0.0024 (14)
C22	0.0258 (16)	0.038 (2)	0.0273 (15)	−0.0027 (16)	0.0078 (13)	0.0013 (15)
N21	0.0268 (14)	0.0352 (16)	0.0270 (14)	0.0011 (14)	0.0059 (11)	0.0019 (13)
C23	0.0232 (17)	0.049 (3)	0.0354 (18)	0.0028 (17)	0.0053 (14)	0.0065 (17)
C24	0.0294 (17)	0.063 (3)	0.0396 (18)	0.002 (2)	0.0134 (15)	0.010 (2)
S21	0.0314 (5)	0.0806 (8)	0.0545 (6)	0.0113 (6)	0.0163 (4)	0.0123 (6)
C25	0.047 (2)	0.101 (5)	0.069 (3)	−0.006 (3)	0.033 (2)	0.005 (3)
N1	0.0312 (15)	0.0415 (18)	0.0275 (14)	−0.0057 (15)	0.0039 (12)	−0.0010 (16)
O11	0.0448 (16)	0.0495 (19)	0.0451 (16)	−0.0048 (16)	0.0079 (13)	0.0129 (15)
O12	0.073 (2)	0.050 (2)	0.0351 (16)	0.0018 (16)	0.0186 (14)	−0.0063 (14)
O13	0.085 (2)	0.0420 (16)	0.0289 (12)	−0.0055 (18)	0.0162 (13)	−0.0043 (14)
N2	0.0374 (17)	0.0390 (18)	0.0292 (16)	−0.0019 (16)	0.0034 (13)	0.0012 (15)
O21	0.089 (3)	0.0444 (18)	0.0494 (18)	−0.001 (2)	0.0208 (17)	0.0123 (16)
O22	0.085 (2)	0.0423 (16)	0.0281 (13)	0.0044 (18)	0.0131 (13)	0.0001 (13)
O23	0.0570 (18)	0.0394 (16)	0.0313 (13)	0.0002 (16)	0.0118 (12)	−0.0011 (14)

Geometric parameters (Å, º) top

O1A—C11	1.194 (5)	C22—N21	1.481 (4)
O1B—C11	1.299 (5)	C22—C23	1.532 (5)
C11—C12	1.520 (5)	C23—C24	1.511 (5)
C12—N11	1.491 (4)	C24—S21	1.805 (4)
C12—C13	1.531 (5)	S21—C25	1.782 (5)
C13—C14	1.511 (5)	N1—O11	1.231 (5)
C14—S11	1.807 (4)	N1—O12	1.251 (5)
S11—C15	1.774 (7)	N1—O13	1.254 (4)
O2A—C21	1.199 (5)	N2—O21	1.223 (5)
O2B—C21	1.307 (5)	N2—O22	1.249 (4)
C21—C22	1.515 (5)	N2—O23	1.257 (5)

O1A—C11—O1B	126.7 (3)	N21—C22—C21	109.1 (3)
O1A—C11—C12	123.5 (3)	N21—C22—C23	111.0 (3)
O1B—C11—C12	109.8 (3)	C21—C22—C23	108.7 (3)
N11—C12—C11	108.5 (3)	C24—C23—C22	113.7 (3)
N11—C12—C13	111.3 (3)	C23—C24—S21	108.7 (3)
C11—C12—C13	110.2 (3)	C25—S21—C24	100.2 (2)
C14—C13—C12	113.2 (3)	O11—N1—O12	122.4 (3)
C13—C14—S11	113.7 (3)	O11—N1—O13	119.8 (4)
C15—S11—C14	100.6 (2)	O12—N1—O13	117.8 (4)
O2A—C21—O2B	125.6 (3)	O21—N2—O22	120.8 (4)
O2A—C21—C22	123.0 (3)	O21—N2—O23	121.5 (3)
O2B—C21—C22	111.3 (3)	O22—N2—O23	117.7 (3)

O1A—C11—C12—N11	−27.6 (5)	O2A—C21—C22—N21	−31.6 (5)
O1B—C11—C12—N11	153.5 (3)	O2B—C21—C22—N21	151.7 (3)
O1A—C11—C12—C13	94.5 (4)	O2A—C21—C22—C23	89.5 (4)
O1B—C11—C12—C13	−84.4 (4)	O2B—C21—C22—C23	−87.2 (4)
N11—C12—C13—C14	−72.4 (5)	N21—C22—C23—C24	−66.6 (5)
C11—C12—C13—C14	167.1 (4)	C21—C22—C23—C24	173.4 (3)
C12—C13—C14—S11	−178.3 (3)	C22—C23—C24—S21	−178.5 (3)
C13—C14—S11—C15	−85.7 (4)	C23—C24—S21—C25	176.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O23ⁱ	0.82	1.90	2.663 (4)	156
O2B—H2B···O12ⁱⁱ	0.82	1.85	2.615 (4)	154
N11—H11C···O1Aⁱⁱⁱ	0.89	2.08	2.859 (4)	145
N11—H11A···O13	0.89	2.50	2.934 (5)	111
N11—H11A···O11	0.89	2.22	3.072 (4)	161
N11—H11B···O13^iv	0.89	2.01	2.854 (5)	158
N21—H21A···O23	0.89	2.13	2.988 (4)	162
N21—H21A···O22	0.89	2.51	2.943 (5)	111
N21—H21B···O22^iv	0.89	2.00	2.840 (5)	157
N21—H21C···O2A^v	0.89	2.10	2.867 (4)	144
N21—H21C···O11	0.89	2.59	3.028 (4)	111

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

L-Me­thioninium nitrate

Supporting information

Key indicators

checkCIF results

L-Methioninium nitrate