Bis(dl-me­thioninium) sulfate

Ramaswamy, S.; Sridhar, B.; Ramakrishnan, V.; Rajaram, R.K.

doi:10.1107/S1600536804021324

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Bis(DL-methioninium) sulfate

S. Ramaswamy, B. Sridhar, V. Ramakrishnan and R. K. Rajaram

In the title compound, 2C₅H₁₂NO₂S⁺·SO₄²⁻, the sulfate anion forms a strong O—H

O hydrogen bond with a methioninium residue. The S atom (S^δ) of the methioninium residue is disordered. The packing reveals aggregation of the methioninium cations as a cylindrical cage along the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021324/ci6427sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021324/ci6427Isup2.hkl Contains datablock I

CCDC reference: 252969

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.061
wR factor = 0.178
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.02 Ratio
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors  for         C5
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        S1'
PLAT432_ALERT_2_B Short Inter X...Y Contact  O22    ..  C1      ..       2.81 Ang.

Alert level C
WEIGH01_ALERT_1_C  Extra text has been found in the
            _refine_ls_weighting_scheme field. This should be in the
            _refine_ls_weighting_details field.
            Weighting scheme given as calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+13.3806P
            Weighting scheme identified as calc
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         C4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         S1
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         S2
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         S3
PLAT301_ALERT_3_C Main Residue  Disorder .........................      21.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.27 Ratio

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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.

Bis(DL-methioninium) sulfate top

Crystal data top

2C₅H₁₂NO₂S⁺·SO₄²⁻	D_x = 1.467 Mg m⁻³ D_m = 1.465 Mg m⁻³ D_m measured by Flotation technique using mixture of carbon tetrachloride and xylene
M_r = 396.49	Mo Kα radiation, λ = 0.71069 Å
Trigonal, R3	Cell parameters from 25 reflections
Hall symbol: -R 3	θ = 9.7–15.5°
a = 10.233 (5) Å	µ = 0.45 mm⁻¹
c = 44.494 (5) Å	T = 293 K
V = 4035 (3) Å³	Block, colourless
Z = 9	0.3 × 0.2 × 0.15 mm
F(000) = 1890

Data collection top

MACH3-Nonius sealed tube diffractometer	1332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω–2θ scans	h = −12→10
Absorption correction: ψ scan (North et al., 1968)	k = −1→12
T_min = 0.897, T_max = 0.935	l = −52→52
5569 measured reflections	3 standard reflections every 60 min
1584 independent reflections	intensity decay: none

Refinement top

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.178	Calculated w = 1/[σ²(F_o²) + (0.085P)² + 13.3806P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.003
1576 reflections	Δρ_max = 0.66 e Å⁻³
124 parameters	Δρ_min = −0.35 e Å⁻³
16 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: none

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	Occ. (<1)
S1	0.5952 (5)	−0.0821 (5)	0.19158 (8)	0.1213 (17)	0.556 (5)
S1'	0.6555 (5)	0.1059 (5)	0.20543 (8)	0.1037 (18)	0.444 (5)
O1	0.3105 (3)	−0.0777 (3)	0.30396 (7)	0.0528 (8)
O2	0.3511 (3)	0.0639 (4)	0.26343 (7)	0.0585 (9)
H2A	0.2738	0.0624	0.2689	0.070*
N1	0.5857 (3)	−0.0387 (4)	0.30463 (7)	0.0436 (8)
H1A	0.5090	−0.1227	0.3121	0.065*
H1B	0.6145	0.0359	0.3179	0.065*
H1C	0.6625	−0.0538	0.3008	0.065*
C1	0.3868 (4)	−0.0080 (4)	0.28296 (9)	0.0404 (9)
C2	0.5376 (4)	0.0022 (5)	0.27645 (9)	0.0460 (10)
H2	0.6111	0.1077	0.2719	0.055*
C3	0.5367 (6)	−0.0921 (7)	0.25088 (10)	0.0656 (13)
H3A	0.4538	−0.1943	0.2536	0.079*
H3B	0.6296	−0.0957	0.2513	0.079*
C4	0.5214 (9)	−0.0366 (11)	0.22050 (13)	0.114 (3)
H4A	0.5689	0.0725	0.2213	0.137*	0.556 (5)
H4B	0.4149	−0.0761	0.2165	0.137*	0.556 (5)
H4C	0.4386	−0.0180	0.2218	0.137*	0.444 (5)
H4D	0.4919	−0.1188	0.2068	0.137*	0.444 (5)
C5	0.7907 (10)	0.0228 (14)	0.1990 (2)	0.162 (4)
H5A	0.8447	0.0050	0.1834	0.195*	0.556 (5)
H5B	0.8112	−0.0080	0.2180	0.195*	0.556 (5)
H5C	0.8224	0.1283	0.1997	0.195*	0.556 (5)
H5D	0.8824	0.0981	0.1897	0.195*	0.444 (5)
H5E	0.7422	−0.0641	0.1863	0.195*	0.444 (5)
H5F	0.8132	−0.0051	0.2181	0.195*	0.444 (5)
S2	0.6667	0.3333	0.3333	0.0364 (6)
O21	0.6667	0.3333	0.3665 (2)	0.057 (3)	0.50
O22	0.5118 (6)	0.2406 (7)	0.32223 (14)	0.0591 (16)	0.50
S3	1.0000	0.0000	0.29659 (3)	0.0332 (5)
O31	1.0000	0.0000	0.32923 (11)	0.0555 (13)
O32	0.8842 (3)	0.0329 (3)	0.28512 (7)	0.0468 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.154 (4)	0.135 (3)	0.091 (2)	0.085 (3)	−0.014 (2)	−0.032 (2)
S1'	0.105 (3)	0.111 (3)	0.074 (2)	0.037 (3)	0.002 (2)	0.020 (2)
O1	0.0344 (14)	0.0509 (17)	0.0727 (19)	0.0209 (13)	0.0087 (13)	0.0169 (14)
O2	0.0535 (18)	0.078 (2)	0.0657 (18)	0.0495 (17)	0.0121 (14)	0.0200 (16)
N1	0.0331 (16)	0.0401 (17)	0.062 (2)	0.0217 (14)	−0.0071 (14)	−0.0111 (14)
C1	0.0342 (19)	0.0344 (18)	0.055 (2)	0.0191 (16)	−0.0017 (17)	−0.0011 (16)
C2	0.040 (2)	0.045 (2)	0.062 (2)	0.0273 (18)	0.0059 (17)	0.0075 (18)
C3	0.064 (3)	0.085 (4)	0.064 (3)	0.050 (3)	0.000 (2)	−0.007 (2)
C4	0.115 (5)	0.196 (7)	0.076 (4)	0.111 (5)	0.003 (4)	0.006 (4)
C5	0.124 (6)	0.218 (9)	0.136 (6)	0.079 (6)	0.037 (5)	0.004 (6)
S2	0.0216 (7)	0.0216 (7)	0.0660 (15)	0.0108 (3)	0.000	0.000
O21	0.056 (4)	0.056 (4)	0.059 (6)	0.0281 (19)	0.000	0.000
O22	0.024 (3)	0.050 (3)	0.087 (4)	0.006 (2)	−0.007 (3)	0.003 (3)
S3	0.0217 (5)	0.0217 (5)	0.0563 (10)	0.0109 (3)	0.000	0.000
O31	0.0538 (19)	0.0538 (19)	0.059 (3)	0.0269 (9)	0.000	0.000
O32	0.0280 (13)	0.0321 (13)	0.084 (2)	0.0176 (11)	−0.0034 (12)	0.0057 (12)

Geometric parameters (Å, º) top

S1—C4	1.672 (7)	C5—H5C	0.96
S1—C5	1.765 (10)	C5—H5D	0.96
S1'—C4	1.568 (9)	C5—H5E	0.96
S1'—C5	1.974 (11)	C5—H5F	0.96
O1—C1	1.198 (5)	S2—O22ⁱ	1.467 (5)
O2—C1	1.303 (5)	S2—O22	1.467 (5)
O2—H2A	0.82	S2—O22ⁱⁱ	1.467 (5)
N1—C2	1.482 (5)	S2—O22ⁱⁱⁱ	1.467 (5)
N1—H1A	0.89	S2—O22^iv	1.467 (5)
N1—H1B	0.89	S2—O22^v	1.467 (5)
N1—H1C	0.89	S2—O21ⁱⁱⁱ	1.476 (10)
C1—C2	1.522 (5)	S2—O21	1.475 (10)
C2—C3	1.489 (6)	O21—O22^iv	1.694 (8)
C2—H2	0.98	O21—O22ⁱⁱⁱ	1.694 (8)
C3—C4	1.504 (8)	O21—O22^v	1.694 (8)
C3—H3A	0.97	O22—O21ⁱⁱⁱ	1.694 (8)
C3—H3B	0.97	O22—O22^v	1.699 (8)
C4—H4A	0.97	O22—O22^iv	1.699 (8)
C4—H4B	0.97	S3—O31	1.452 (5)
C4—H4C	0.96	S3—O32^vi	1.475 (2)
C4—H4D	0.96	S3—O32	1.475 (2)
C5—H5A	0.96	S3—O32^vii	1.475 (2)
C5—H5B	0.96

C4—S1—C5	102.6 (5)	H5A—C5—H5F	109.7
C4—S1'—C5	97.9 (5)	H5C—C5—H5F	108.0
C1—O2—H2A	109.5	H5D—C5—H5F	109.6
C2—N1—H1A	109.5	H5E—C5—H5F	109.7
C2—N1—H1B	109.5	O22ⁱ—S2—O22	109.3 (3)
H1A—N1—H1B	109.5	O22ⁱ—S2—O22ⁱⁱ	109.3 (3)
C2—N1—H1C	109.5	O22—S2—O22ⁱⁱ	109.3 (3)
H1A—N1—H1C	109.5	O22ⁱ—S2—O22ⁱⁱⁱ	70.7 (3)
H1B—N1—H1C	109.5	O22—S2—O22ⁱⁱⁱ	179.995 (2)
O1—C1—O2	124.9 (3)	O22ⁱⁱ—S2—O22ⁱⁱⁱ	70.7 (3)
O1—C1—C2	121.8 (3)	O22ⁱ—S2—O22^iv	70.7 (3)
O2—C1—C2	113.3 (3)	O22—S2—O22^iv	70.7 (3)
N1—C2—C3	111.1 (3)	O22ⁱⁱ—S2—O22^iv	180.0 (5)
N1—C2—C1	106.7 (3)	O22ⁱⁱⁱ—S2—O22^iv	109.3 (3)
C3—C2—C1	115.0 (4)	O22ⁱ—S2—O22^v	179.996 (5)
N1—C2—H2	107.9	O22—S2—O22^v	70.7 (3)
C3—C2—H2	107.9	O22ⁱⁱ—S2—O22^v	70.7 (3)
C1—C2—H2	107.9	O22ⁱⁱⁱ—S2—O22^v	109.3 (3)
C2—C3—C4	114.2 (5)	O22^iv—S2—O22^v	109.3 (3)
C2—C3—H3A	108.7	O22ⁱ—S2—O21ⁱⁱⁱ	70.3 (2)
C4—C3—H3A	108.7	O22—S2—O21ⁱⁱⁱ	70.3 (2)
C2—C3—H3B	108.7	O22ⁱⁱ—S2—O21ⁱⁱⁱ	70.3 (2)
C4—C3—H3B	108.7	O22ⁱⁱⁱ—S2—O21ⁱⁱⁱ	109.7 (2)
H3A—C3—H3B	107.6	O22^iv—S2—O21ⁱⁱⁱ	109.7 (2)
C3—C4—S1'	121.8 (6)	O22^v—S2—O21ⁱⁱⁱ	109.7 (2)
C3—C4—S1	116.1 (5)	O22ⁱ—S2—O21	109.7 (2)
C3—C4—H4A	108.3	O22—S2—O21	109.7 (2)
S1—C4—H4A	108.3	O22ⁱⁱ—S2—O21	109.7 (2)
C3—C4—H4B	108.3	O22ⁱⁱⁱ—S2—O21	70.3 (2)
S1'—C4—H4B	126.0	O22^iv—S2—O21	70.3 (2)
S1—C4—H4B	108.3	O22^v—S2—O21	70.3 (2)
H4A—C4—H4B	107.4	O21ⁱⁱⁱ—S2—O21	179.998 (1)
C3—C4—H4C	106.8	S2—O21—O22^iv	54.6 (3)
S1'—C4—H4C	106.9	S2—O21—O22ⁱⁱⁱ	54.6 (3)
S1—C4—H4C	132.1	O22^iv—O21—O22ⁱⁱⁱ	89.8 (5)
C3—C4—H4D	106.8	S2—O21—O22^v	54.6 (3)
S1'—C4—H4D	106.7	O22^iv—O21—O22^v	89.8 (5)
H4C—C4—H4D	107.0	O22ⁱⁱⁱ—O21—O22^v	89.8 (5)
S1—C5—H5A	109.5	S2—O22—O21ⁱⁱⁱ	55.1 (3)
S1—C5—H5B	109.5	S2—O22—O22^v	54.63 (13)
S1'—C5—H5B	109.3	O21ⁱⁱⁱ—O22—O22^v	90.3 (3)
H5A—C5—H5B	109.5	S2—O22—O22^iv	54.63 (13)
S1—C5—H5C	109.5	O21ⁱⁱⁱ—O22—O22^iv	90.3 (3)
H5A—C5—H5C	109.5	O22^v—O22—O22^iv	89.5 (5)
H5B—C5—H5C	109.5	O31—S3—O32^vi	110.24 (13)
S1'—C5—H5D	109.3	O31—S3—O32	110.24 (13)
H5B—C5—H5D	110.7	O32^vi—S3—O32	108.69 (13)
S1'—C5—H5E	109.6	O31—S3—O32^vii	110.24 (13)
H5B—C5—H5E	108.3	O32^vi—S3—O32^vii	108.69 (13)
H5D—C5—H5E	109.6	O32—S3—O32^vii	108.69 (13)
S1'—C5—H5F	109.0

O1—C1—C2—N1	−18.9 (5)	O22—S2—O21—O22ⁱⁱⁱ	179.998 (1)
O2—C1—C2—N1	161.9 (3)	O22ⁱⁱ—S2—O21—O22ⁱⁱⁱ	−60.002 (1)
O1—C1—C2—C3	104.8 (5)	O22ⁱ—S2—O21—O22^v	180.000 (6)
O2—C1—C2—C3	−74.4 (5)	O22—S2—O21—O22^v	−60.000 (6)
N1—C2—C3—C4	−167.7 (5)	O22ⁱⁱ—S2—O21—O22^v	60.000 (6)
C1—C2—C3—C4	70.9 (6)	O22^iv—S2—O21—O22^v	−120.000 (6)
C2—C3—C4—S1'	74.1 (7)	O22ⁱ—S2—O22—O21ⁱⁱⁱ	−59.7 (3)
C2—C3—C4—S1	153.2 (5)	O22ⁱⁱ—S2—O22—O21ⁱⁱⁱ	59.7 (3)
C5—S1'—C4—C3	66.7 (7)	O22^iv—S2—O22—O21ⁱⁱⁱ	−120.3 (3)
C5—S1'—C4—S1	−41.1 (4)	O22^v—S2—O22—O21ⁱⁱⁱ	120.3 (3)
C5—S1—C4—C3	−67.5 (8)	O21—S2—O22—O21ⁱⁱⁱ	180.002 (2)
C5—S1—C4—S1'	48.3 (5)	O22ⁱ—S2—O22—O22^v	180.003 (2)
C4—S1—C5—S1'	−40.6 (4)	O22ⁱⁱ—S2—O22—O22^v	−60.5 (6)
C4—S1'—C5—S1	43.1 (4)	O22^iv—S2—O22—O22^v	119.5 (6)
O22ⁱ—S2—O21—O22^iv	−60.000 (2)	O21—S2—O22—O22^v	59.7 (3)
O22—S2—O21—O22^iv	60.000 (2)	O22ⁱ—S2—O22—O22^iv	60.5 (6)
O22ⁱⁱ—S2—O21—O22^iv	180.000 (2)	O22ⁱⁱ—S2—O22—O22^iv	180.0
O22ⁱⁱⁱ—S2—O21—O22^iv	−119.998 (2)	O22^v—S2—O22—O22^iv	−119.5 (6)
O22^v—S2—O21—O22^iv	120.000 (2)	O21ⁱⁱⁱ—S2—O22—O22^iv	120.3 (3)
O22ⁱ—S2—O21—O22ⁱⁱⁱ	59.998 (1)	O21—S2—O22—O22^iv	−59.7 (3)

Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) −x+4/3, −y+2/3, −z+2/3; (iv) x−y+1/3, x−1/3, −z+2/3; (v) y+1/3, −x+y+2/3, −z+2/3; (vi) −y+1, x−y−1, z; (vii) −x+y+2, −x+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O32ⁱⁱ	0.82	1.78	2.570 (4)	162
N1—H1A···O31^viii	0.89	2.30	3.179 (4)	172
N1—H1B···O22^iv	0.89	1.92	2.772 (7)	160
N1—H1B···O22ⁱ	0.89	2.11	2.862 (7)	141
N1—H1C···O32	0.89	2.10	2.895 (4)	148
N1—H1C···O1^ix	0.89	2.41	2.924 (4)	117

Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iv) x−y+1/3, x−1/3, −z+2/3; (viii) −x+4/3, −y−1/3, −z+2/3; (ix) −x+y+1, −x, z.

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