Sodium 2-mercaptoethanesulfonate monohydrate (coenzyme M sodium salt monohydrate)

Mayr, S.; Günther, D.; Jaun, B.; Schweizer, W.B.

doi:10.1107/S1600536808031814

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1476-m1477

doi:10.1107/S1600536808031814

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Sodium 2-mercaptoethanesulfonate monohydrate (coenzyme M sodium salt monohydrate)

Stefan Mayr,^a Detlef Günther,^b Bernhard Jaun ^a and W. Bernd Schweizer ^a ^*

^aLaboratory of Organic Chemistry, ETH Zurich, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland, and ^bLaboratory of Inorganic Chemistry, ETH Zurich, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland
^*Correspondence e-mail: schweizer@org.chem.ethz.ch

(Received 19 August 2008; accepted 2 October 2008; online 31 October 2008)

The 2-thioethanesulfonate anion is the smallest known coenzyme in nature (HS–CoM) and plays a key role in methanogenesis by anaerobic archaea, as well as in the oxidation of alkenes by Gram-negative and Gram-positive eubacteria. The title compound, Na⁺·C₂H₅O₃S₂⁻·H₂O, is the Na⁺ salt of HS–CoM crystallized as the monohydrate. Six O atoms form a distorted octahedral coordination geometry around the Na atom, at distances in the range 2.312 (4)–2.517 (3) Å. Two O atoms of the sulfonate group, one O atom of each of three other symmetry-related sulfonate groups plus the water O atom form the coordination environment of the Na⁺ ion. This arrangement forms Na–O–Na layers in the crystal structure, parallel to (100).

Related literature

For related literature about HS–CoM, see: Allen et al. (1999 ); Bruchhausen et al. (1993 ); Günther & Hattendorf (2005 ); Graham et al. (2002 ); Latkoczy & Günther (2002 ); Mackay et al. (1999 ); Schramm et al. (1955 ); Thauer (1998 ). For the structure of the unhydrated Na HS–CoM salt, see: Bambagiotti-Alberti et al. (2007 ).

Experimental

Crystal data

Na⁺·C₂H₅O₃S₂⁻·H₂O
M_r = 182.19
Orthorhombic, P n a 2₁
a = 23.4301 (8) Å
b = 5.0324 (2) Å
c = 6.1254 (2) Å
V = 722.24 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 223 K
0.26 × 0.20 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
1647 measured reflections
1534 independent reflections
1263 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.131
S = 0.95
1534 reflections
88 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 627 Friedel pairs
Flack parameter: 0.13 (18)

Table 1
Selected bond lengths (Å)

Na9—O5ⁱ	2.312 (4)
Na9—O8ⁱⁱ	2.322 (4)
Na9—O7	2.404 (3)
Na9—O6ⁱⁱⁱ	2.416 (2)
Na9—O5	2.456 (3)
Na9—O8	2.517 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y-1, z.

Data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek 2003 ); software used to prepare material for publication: maXus (Mackay et al., 1999).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031814/bh2190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031814/bh2190Isup2.hkl

checkCIF report

Comment top

The title compound includes 2-thioethanesulfonate ion, the smallest known coenzyme in nature, coenzyme M, which plays a key role in methanogenesis by anaerobic archaea (Thauer, 1998) and in the oxidation of alkenes by gram-negative and gram-positive eubacteria (Allen et al., 1999). Furthermore its sodium salt (mesna) is medically used as mucolytics and to prevent urotoxic side effects of certain anticancer drugs (Bruchhausen et al., 1993). Whereas the biosynthesis of coenzyme M starts by sulfitation of phosphoenolpyruvate (Graham et al., 2002), the chemical synthesis begins from sodium 2-bromoethanesulfonate and thiourea in ammoniacal solution (Bruchhausen et al., 1993). Since 2-thioethanesulfonic acid represents a highly viscous oil decomposing under release of hydrogen sulfide at room temperature, it is usually stored and sold as stable sodium or ammonium salt (Schramm et al., 1955). The title compound is the monohydrate of the sodium salt.

Six O atoms show a distorted octahedral coordination geometry around the Na atom at distances in the range of 2.312 (4)–2.517 (3) Å (Fig. 1). Two O atoms of a SO₃ group and one O of three other SO₃ groups plus the water O atom form the coordination sphere of the Na⁺ ion. This forms Na–O–Na layers parallel to (100) in the crystal (Fig. 2).

The crystal structure of the unhydrated form (Bambagiotti-Alberti et al., 2007; CSD refcode UDUVUL) shows a similar six-fold coordination of the Na atom where the water O atom is replaced by an O-atom of a SO₃ group. The conformation of the S atoms is antiperiplanar in our compound and gauche in the unhydrated form.

Related literature top

For related literature about HS–CoM, see: Allen et al. (1999); Bruchhausen et al. (1993); Günther & Hattendorf (2005); Graham et al. (2002); Latkoczy & Günther (2002); Mackay et al. (1999); Schramm et al. (1955); Thauer (1998). For the structure of the unhydrated Na HS–CoM salt, see: Bambagiotti-Alberti et al. (2007).

Experimental top

When adding pure ethanol to a concentrated solution of 2-thioethanesulfonic acid in water, we noticed a precipitating white crystalline mass never described before in the literature. Micro elementary analysis based on the empirical formula (C₂H₈O₄S₂) of the hydrated acid (HS–CoM^-H₃O⁺) showed significantly low values for C and H. At the same time ¹H and ¹³C NMR analysis of the precipitate in D₂O ruled out any organic impurities. Investigations into the crystals by laser ablation inductively coupled plasma sector field mass spectrometry (LA-ICP-SF MS), however, clearly revealed the presence of sodium in hyperstoichiometric amounts: molar ratio (Na-23)/(S-32) = 1.34 (RSD: 8,5%, n = 9) (Günther & Hattendorf, 2005; Latkoczy & Günther, 2002). The white precipitate consisted of two different types of crystals, needles and thin plates. The needles were used for structure analysis by X-ray diffraction.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek 2003); software used to prepare material for publication: maXus (Mackay et al., 1999).

Figures top

	Fig. 1. The molecular structure of sodium 2-thioethanesulfonate hydrate with 50% probability displacement ellipsoids. H atoms are omitted for clarity. The complete coordination of the Na atom is shown. Symmetry codes: (a) x, -1+y, z; (b) x, 1+y, z; (c) 1/2-x, -1/2+y, -1/2+z; (d) 1/2-x, -1/2+y, 1/2+z; (e) 1/2-x, 1/2+y, -1/2+z; (f) 1/2-x, 1/2+y, 1/2+z.
	Fig. 2. Crystal structure viewed down the diagonal of the a–b axis, showing the layer structure of Na—O clusters.

sodium 2-mercaptoethanesulfonate monohydrate top

Crystal data top

Na⁺·C₂H₅O₃S₂⁻·H₂O	D_x = 1.676 Mg m⁻³
M_r = 182.19	Melting point: 473 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5975 reflections
a = 23.4301 (8) Å	θ = 2.3–27.5°
b = 5.0324 (2) Å	µ = 0.74 mm⁻¹
c = 6.1254 (2) Å	T = 223 K
V = 722.24 (4) Å³	Plate, colourless
Z = 4	0.26 × 0.20 × 0.01 mm
F(000) = 376.0

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.065
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.4°
CCD scans	h = −29→30
1647 measured reflections	k = −6→6
1534 independent reflections	l = −7→7
1263 reflections with I > 2σ(I)

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max < 0.001
1534 reflections	Δρ_max = 0.25 e Å⁻³
88 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 627 Friedel pairs
0 constraints	Absolute structure parameter: 0.13 (18)

Crystal data top

Na⁺·C₂H₅O₃S₂⁻·H₂O	V = 722.24 (4) Å³
M_r = 182.19	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 23.4301 (8) Å	µ = 0.74 mm⁻¹
b = 5.0324 (2) Å	T = 223 K
c = 6.1254 (2) Å	0.26 × 0.20 × 0.01 mm

Data collection top

Nonius KappaCCD diffractometer	1263 reflections with I > 2σ(I)
1647 measured reflections	R_int = 0.065
1534 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.25 e Å⁻³
S = 0.95	Δρ_min = −0.37 e Å⁻³
1534 reflections	Absolute structure: Flack (1983), 627 Friedel pairs
88 parameters	Absolute structure parameter: 0.13 (18)
1 restraint

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

	x	y	z	U_iso*/U_eq
S3	−0.00830 (4)	0.7465 (2)	0.8298 (4)	0.0483 (4)
H3	−0.0154	0.8542	0.6813	0.058*
S4	0.17410 (3)	0.75424 (11)	0.66676 (19)	0.0185 (2)
Na9	0.26442 (4)	0.3309 (2)	0.6658 (4)	0.0238 (3)
O5	0.19813 (10)	0.6264 (6)	0.4720 (5)	0.0239 (7)
O6	0.18238 (8)	1.0402 (4)	0.6710 (8)	0.0286 (5)
O7	0.33586 (10)	0.6737 (5)	0.6717 (8)	0.0338 (5)
H1	0.3259	0.8098	0.7595	0.023 (11)*
H2	0.3374	0.7465	0.5332	0.047 (16)*
O8	0.19475 (10)	0.6245 (6)	0.8649 (5)	0.0257 (7)
C1	0.06798 (17)	0.8051 (9)	0.8424 (9)	0.0464 (11)
H1A	0.0756	1.0166	0.8509	0.056*
H1B	0.0846	0.7169	0.9900	0.056*
C2	0.09943 (14)	0.6946 (6)	0.6517 (10)	0.0279 (8)
H2A	0.0829	0.7827	0.5039	0.033*
H2B	0.0920	0.4830	0.6431	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S3	0.0235 (5)	0.0688 (8)	0.0526 (8)	−0.0031 (4)	0.0074 (6)	0.0024 (6)
S4	0.0182 (4)	0.0178 (4)	0.0194 (4)	−0.00146 (19)	0.0008 (4)	0.0002 (7)
Na9	0.0267 (6)	0.0228 (6)	0.0219 (6)	0.0034 (4)	−0.0009 (9)	−0.0004 (10)
O5	0.0302 (16)	0.0223 (15)	0.0191 (18)	−0.0013 (11)	0.0050 (14)	−0.0031 (12)
O6	0.0325 (10)	0.0188 (10)	0.0344 (12)	−0.0029 (8)	0.0011 (17)	−0.003 (2)
O7	0.0398 (13)	0.0345 (11)	0.0271 (13)	0.0012 (10)	0.004 (2)	−0.005 (2)
O8	0.0301 (16)	0.0271 (17)	0.0197 (18)	0.0020 (12)	−0.0011 (13)	−0.0027 (14)
C1	0.0228 (17)	0.063 (3)	0.053 (3)	−0.0050 (17)	0.010 (2)	−0.013 (3)
C2	0.0182 (14)	0.0364 (16)	0.029 (2)	−0.0033 (12)	−0.001 (2)	−0.008 (2)

Geometric parameters (Å, º) top

S3—C1	1.813 (4)	Na9—Na9ⁱ	4.0207 (5)
S3—H3	1.0714	Na9—Na9ⁱⁱ	4.0207 (5)
S4—O6	1.4522 (19)	Na9—Na9^v	4.0207 (5)
S4—O8	1.460 (4)	O5—Na9^v	2.312 (4)
S4—O5	1.468 (3)	O6—Na9^vi	2.416 (2)
S4—C2	1.778 (3)	O7—H1	0.9012
S4—Na9	3.0028 (13)	O7—H2	0.9247
Na9—O5ⁱ	2.312 (4)	O8—Na9^iv	2.322 (4)
Na9—O8ⁱⁱ	2.322 (4)	C1—C2	1.489 (6)
Na9—O7	2.404 (3)	C1—H1A	1.0800
Na9—O6ⁱⁱⁱ	2.416 (2)	C1—H1B	1.0800
Na9—O5	2.456 (3)	C2—H2A	1.0800
Na9—O8	2.517 (3)	C2—H2B	1.0800
Na9—Na9^iv	4.0207 (5)

C1—S3—H3	96.1	O8—Na9—Na9ⁱ	83.64 (8)
O6—S4—O8	112.6 (2)	S4—Na9—Na9ⁱ	108.91 (6)
O6—S4—O5	113.4 (2)	Na9^iv—Na9—Na9ⁱ	77.477 (11)
O8—S4—O5	110.64 (11)	O5ⁱ—Na9—Na9ⁱⁱ	113.78 (8)
O6—S4—C2	107.43 (13)	O8ⁱⁱ—Na9—Na9ⁱⁱ	35.38 (7)
O8—S4—C2	107.1 (2)	O7—Na9—Na9ⁱⁱ	125.28 (13)
O5—S4—C2	105.2 (2)	O6ⁱⁱⁱ—Na9—Na9ⁱⁱ	59.83 (11)
O6—S4—Na9	127.52 (9)	O5—Na9—Na9ⁱⁱ	84.52 (8)
O8—S4—Na9	56.70 (12)	O8—Na9—Na9ⁱⁱ	128.86 (8)
O5—S4—Na9	54.35 (12)	S4—Na9—Na9ⁱⁱ	109.09 (5)
C2—S4—Na9	125.01 (11)	Na9^iv—Na9—Na9ⁱⁱ	160.65 (6)
O5ⁱ—Na9—O8ⁱⁱ	106.77 (8)	Na9ⁱ—Na9—Na9ⁱⁱ	99.226 (14)
O5ⁱ—Na9—O7	92.45 (14)	O5ⁱ—Na9—Na9^v	163.76 (8)
O8ⁱⁱ—Na9—O7	92.65 (14)	O8ⁱⁱ—Na9—Na9^v	75.20 (9)
O5ⁱ—Na9—O6ⁱⁱⁱ	91.25 (13)	O7—Na9—Na9^v	71.31 (12)
O8ⁱⁱ—Na9—O6ⁱⁱⁱ	93.87 (12)	O6ⁱⁱⁱ—Na9—Na9^v	104.78 (10)
O7—Na9—O6ⁱⁱⁱ	171.25 (9)	O5—Na9—Na9^v	31.43 (7)
O5ⁱ—Na9—O5	154.34 (14)	O8—Na9—Na9^v	83.84 (8)
O8ⁱⁱ—Na9—O5	98.49 (14)	S4—Na9—Na9^v	55.88 (5)
O7—Na9—O5	90.75 (11)	Na9^iv—Na9—Na9^v	99.226 (14)
O6ⁱⁱⁱ—Na9—O5	82.52 (10)	Na9ⁱ—Na9—Na9^v	160.65 (6)
O5ⁱ—Na9—O8	96.56 (14)	Na9ⁱⁱ—Na9—Na9^v	77.476 (11)
O8ⁱⁱ—Na9—O8	156.12 (14)	S4—O5—Na9^v	127.60 (18)
O7—Na9—O8	91.32 (12)	S4—O5—Na9	96.60 (16)
O6ⁱⁱⁱ—Na9—O8	80.38 (10)	Na9^v—O5—Na9	114.93 (10)
O5—Na9—O8	57.90 (7)	S4—O6—Na9^vi	134.91 (12)
O5ⁱ—Na9—S4	125.55 (10)	Na9—O7—H1	112.0
O8ⁱⁱ—Na9—S4	127.54 (10)	Na9—O7—H2	107.3
O7—Na9—S4	88.94 (7)	H1—O7—H2	104.9
O6ⁱⁱⁱ—Na9—S4	82.46 (6)	S4—O8—Na9^iv	126.59 (19)
O5—Na9—S4	29.05 (8)	S4—O8—Na9	94.29 (16)
O8—Na9—S4	29.01 (8)	Na9^iv—O8—Na9	112.33 (10)
O5ⁱ—Na9—Na9^iv	74.00 (8)	C2—C1—S3	113.2 (3)
O8ⁱⁱ—Na9—Na9^iv	162.52 (8)	C2—C1—H1A	108.9
O7—Na9—Na9^iv	69.91 (11)	S3—C1—H1A	108.9
O6ⁱⁱⁱ—Na9—Na9^iv	103.59 (10)	C2—C1—H1B	108.9
O5—Na9—Na9^iv	83.28 (8)	S3—C1—H1B	108.9
O8—Na9—Na9^iv	32.29 (7)	H1A—C1—H1B	107.8
S4—Na9—Na9^iv	55.67 (5)	C1—C2—S4	112.5 (3)
O5ⁱ—Na9—Na9ⁱ	33.64 (7)	C1—C2—H2A	109.1
O8ⁱⁱ—Na9—Na9ⁱ	113.20 (9)	S4—C2—H2A	109.1
O7—Na9—Na9ⁱ	123.68 (13)	C1—C2—H2B	109.1
O6ⁱⁱⁱ—Na9—Na9ⁱ	58.49 (11)	S4—C2—H2B	109.1
O5—Na9—Na9ⁱ	129.85 (9)	H2A—C2—H2B	107.8

O6—S4—Na9—O5ⁱ	91.9 (3)	O8—Na9—O5—S4	4.61 (8)
O8—S4—Na9—O5ⁱ	−2.37 (19)	Na9^iv—Na9—O5—S4	−16.81 (12)
O5—S4—Na9—O5ⁱ	−174.30 (19)	Na9ⁱ—Na9—O5—S4	50.69 (17)
C2—S4—Na9—O5ⁱ	−90.6 (3)	Na9ⁱⁱ—Na9—O5—S4	148.14 (13)
O6—S4—Na9—O8ⁱⁱ	−92.9 (3)	Na9^v—Na9—O5—S4	−137.0 (2)
O8—S4—Na9—O8ⁱⁱ	172.8 (2)	O5ⁱ—Na9—O5—Na9^v	147.7 (2)
O5—S4—Na9—O8ⁱⁱ	0.92 (18)	O8ⁱⁱ—Na9—O5—Na9^v	−42.28 (14)
C2—S4—Na9—O8ⁱⁱ	84.6 (3)	O7—Na9—O5—Na9^v	50.50 (18)
O6—S4—Na9—O7	−0.3 (3)	O6ⁱⁱⁱ—Na9—O5—Na9^v	−135.11 (15)
O8—S4—Na9—O7	−94.6 (2)	O8—Na9—O5—Na9^v	141.6 (2)
O5—S4—Na9—O7	93.4 (2)	S4—Na9—O5—Na9^v	137.0 (2)
C2—S4—Na9—O7	177.2 (2)	Na9^iv—Na9—O5—Na9^v	120.17 (13)
O6—S4—Na9—O6ⁱⁱⁱ	178.0 (4)	Na9ⁱ—Na9—O5—Na9^v	−172.34 (6)
O8—S4—Na9—O6ⁱⁱⁱ	83.75 (18)	Na9ⁱⁱ—Na9—O5—Na9^v	−74.88 (13)
O5—S4—Na9—O6ⁱⁱⁱ	−88.17 (17)	O8—S4—O6—Na9^vi	67.2 (4)
C2—S4—Na9—O6ⁱⁱⁱ	−4.5 (3)	O5—S4—O6—Na9^vi	−59.3 (4)
O6—S4—Na9—O5	−93.8 (3)	C2—S4—O6—Na9^vi	−175.1 (4)
O8—S4—Na9—O5	171.92 (14)	Na9—S4—O6—Na9^vi	2.7 (5)
C2—S4—Na9—O5	83.7 (3)	O6—S4—O8—Na9^iv	1.0 (3)
O6—S4—Na9—O8	94.3 (3)	O5—S4—O8—Na9^iv	129.03 (19)
O5—S4—Na9—O8	−171.92 (14)	C2—S4—O8—Na9^iv	−116.9 (2)
C2—S4—Na9—O8	−88.2 (3)	Na9—S4—O8—Na9^iv	122.0 (2)
O6—S4—Na9—Na9^iv	65.9 (3)	O6—S4—O8—Na9	−121.06 (16)
O8—S4—Na9—Na9^iv	−28.43 (14)	O5—S4—O8—Na9	7.01 (12)
O5—S4—Na9—Na9^iv	159.65 (14)	C2—S4—O8—Na9	121.08 (15)
C2—S4—Na9—Na9^iv	−116.6 (2)	O5ⁱ—Na9—O8—S4	178.06 (16)
O6—S4—Na9—Na9ⁱ	125.1 (3)	O8ⁱⁱ—Na9—O8—S4	−14.1 (4)
O8—S4—Na9—Na9ⁱ	30.82 (14)	O7—Na9—O8—S4	85.44 (17)
O5—S4—Na9—Na9ⁱ	−141.11 (14)	O6ⁱⁱⁱ—Na9—O8—S4	−91.78 (16)
C2—S4—Na9—Na9ⁱ	−57.4 (2)	O5—Na9—O8—S4	−4.62 (8)
O6—S4—Na9—Na9ⁱⁱ	−127.6 (3)	Na9^iv—Na9—O8—S4	132.6 (2)
O8—S4—Na9—Na9ⁱⁱ	138.14 (14)	Na9ⁱ—Na9—O8—S4	−150.81 (13)
O5—S4—Na9—Na9ⁱⁱ	−33.78 (14)	Na9ⁱⁱ—Na9—O8—S4	−54.07 (17)
C2—S4—Na9—Na9ⁱⁱ	49.9 (2)	Na9^v—Na9—O8—S4	14.40 (12)
O6—S4—Na9—Na9^v	−68.3 (3)	O5ⁱ—Na9—O8—Na9^iv	45.45 (13)
O8—S4—Na9—Na9^v	−162.63 (14)	O8ⁱⁱ—Na9—O8—Na9^iv	−146.7 (2)
O5—S4—Na9—Na9^v	25.45 (14)	O7—Na9—O8—Na9^iv	−47.17 (17)
C2—S4—Na9—Na9^v	109.2 (2)	O6ⁱⁱⁱ—Na9—O8—Na9^iv	135.61 (15)
O6—S4—O5—Na9^v	−8.3 (3)	O5—Na9—O8—Na9^iv	−137.2 (2)
O8—S4—O5—Na9^v	−135.9 (2)	S4—Na9—O8—Na9^iv	−132.6 (2)
C2—S4—O5—Na9^v	108.8 (2)	Na9ⁱ—Na9—O8—Na9^iv	76.58 (13)
Na9—S4—O5—Na9^v	−128.7 (2)	Na9ⁱⁱ—Na9—O8—Na9^iv	173.32 (6)
O6—S4—O5—Na9	120.40 (17)	Na9^v—Na9—O8—Na9^iv	−118.21 (13)
O8—S4—O5—Na9	−7.21 (12)	S3—C1—C2—S4	179.9 (2)
C2—S4—O5—Na9	−122.50 (16)	O6—S4—C2—C1	−60.6 (4)
O5ⁱ—Na9—O5—S4	10.8 (4)	O8—S4—C2—C1	60.6 (4)
O8ⁱⁱ—Na9—O5—S4	−179.26 (15)	O5—S4—C2—C1	178.3 (3)
O7—Na9—O5—S4	−86.47 (18)	Na9—S4—C2—C1	121.5 (3)
O6ⁱⁱⁱ—Na9—O5—S4	87.92 (15)

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

Experimental details

Crystal data
Chemical formula	Na⁺·C₂H₅O₃S₂⁻·H₂O
M_r	182.19
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	223
a, b, c (Å)	23.4301 (8), 5.0324 (2), 6.1254 (2)
V (Å³)	722.24 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.26 × 0.20 × 0.01

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1647, 1534, 1263
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.131, 0.95
No. of reflections	1534
No. of parameters	88
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.37
Absolute structure	Flack (1983), 627 Friedel pairs
Absolute structure parameter	0.13 (18)

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek 2003), maXus (Mackay et al., 1999).

Selected bond lengths (Å) top

Na9—O5ⁱ	2.312 (4)	Na9—O6ⁱⁱⁱ	2.416 (2)
Na9—O8ⁱⁱ	2.322 (4)	Na9—O5	2.456 (3)
Na9—O7	2.404 (3)	Na9—O8	2.517 (3)

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

References

Allen, J. R., Clark, D. D., Krum, J. G. & Ensign, S. A. (1999). Proc. Natl Acad. Sci. USA, 96, 8432–8437. Web of Science CrossRef PubMed CAS Google Scholar
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Bambagiotti-Alberti, M., Bruni, B., Di Vaira, M. & Giannellini, V. (2007). Acta Cryst. E63, o1796. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruchhausen, F. V., Dannhardt, G. & Ebelet, S. (1993). Editors. Hagers Handbuch der Pharmazeutischen Praxis, Vol. 8, p. 890. Berlin, Heidelberg, New York, London, Paris, Tokyo, Hong Kong, Barcelona, Budapest: Springer. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Schramm, C. H., Lemaire, H. & Karlson, R. H. (1955). J. Am. Chem. Soc. 77, 6231–6233. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 64| Part 11| November 2008| Pages m1476-m1477

doi:10.1107/S1600536808031814

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Sodium 2-mercapto­ethane­sulfonate monohydrate (coenzyme M sodium salt monohydrate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Sodium 2-mercaptoethanesulfonate monohydrate (coenzyme M sodium salt monohydrate)