Bis[eth-yl(2-hydroxy-ethyl)aza-nium] 2,2'-disulfanediyldibenzoate.

The asymmetric unit of the title salt, 2C(4)H(12)NO(+)·C(14)H(8)O(4)S(2) (2-), contains an eth-yl(2-hydr-oxy)aminium cation and half a 2,2'-disulfanediyldibenzoate anion, with the latter disposed about a twofold axis. The cation is a straight chain with the exception of the terminal hydr-oxy group [the N-C-C-O torsion angle is 66.5 (2)°]. A twisted conformation is found for the anion [the C-S-S-C torsion angle is 91.51 (9)° and the dihedral angle between the rings is 81.01 (4)°]. A supra-molecular chain with base vector [101] and a tubular topology is formed in the crystal structure mediated by charge-assisted O-H⋯O(-) and N(+)-H⋯O(-) hydrogen bonding.

Related literature

For related studies on co-crystal/salt formation involving 2-[(2-carboxy­phen­yl)disulfan­yl]benzoic acid, see: Broker & Tiekink (2007 ▶); Broker et al. (2008 ▶). For software used to search the Cambridge Structural Database, see: Bruno et al. (2002 ▶).

Experimental

Crystal data

2C4H12NO+·C14H8O4S2 2−

M = 484.64

Monoclinic,

a = 22.949 (5) Å

b = 8.2429 (16) Å

c = 14.766 (3) Å

β = 119.80 (3)°

V = 2423.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 173 K

0.40 × 0.25 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 CCD-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.800, T max = 1.000

7823 measured reflections

2503 independent reflections

2367 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.14

2503 reflections

148 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006781/zs2030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006781/zs2030Isup2.hkl

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

2C4H12NO+·C14H8O4S22−	F(000) = 1032
Mr = 484.64	Dx = 1.328 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5747 reflections
a = 22.949 (5) Å	θ = 3.6–30.5°
b = 8.2429 (16) Å	µ = 0.26 mm−1
c = 14.766 (3) Å	T = 173 K
β = 119.80 (3)°	Block, colourless
V = 2423.9 (11) Å3	0.40 × 0.25 × 0.10 mm
Z = 4

Rigaku AFC12K/SATURN724 CCD-detector diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	2367 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω scans	θmax = 26.5°, θmin = 3.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→25
Tmin = 0.800, Tmax = 1.000	k = −10→10
7823 measured reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0437P)2 + 1.6814P] where P = (Fo2 + 2Fc2)/3
2503 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

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.

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	0.04587 (2)	0.42885 (5)	0.31713 (3)	0.02621 (14)
O1	0.17238 (6)	0.44668 (13)	0.48609 (9)	0.0272 (3)
O2	0.21265 (6)	0.67861 (14)	0.57133 (9)	0.0269 (3)
O3	0.17235 (7)	0.9908 (2)	0.29494 (10)	0.0453 (4)
H3	0.2072	0.9376	0.3338	0.068*
N1	0.20710 (7)	1.00243 (16)	0.51963 (10)	0.0231 (3)
H1A	0.2410	1.0242	0.5052	0.028*
H1B	0.2069	0.8923	0.5296	0.028*
C1	0.16465 (8)	0.58217 (18)	0.51667 (12)	0.0223 (3)
C2	0.09497 (8)	0.63551 (18)	0.48785 (12)	0.0222 (3)
C3	0.03728 (8)	0.57605 (18)	0.39935 (12)	0.0236 (3)
C4	−0.02554 (9)	0.6307 (2)	0.37906 (14)	0.0329 (4)
H4	−0.0647	0.5931	0.3187	0.039*
C5	−0.03181 (10)	0.7382 (2)	0.44505 (15)	0.0376 (4)
H5	−0.0752	0.7728	0.4303	0.045*
C6	0.02468 (9)	0.7965 (2)	0.53293 (14)	0.0335 (4)
H6	0.0203	0.8701	0.5787	0.040*
C7	0.08727 (9)	0.74627 (19)	0.55301 (13)	0.0269 (4)
H7	0.1261	0.7877	0.6124	0.032*
C8	0.12733 (9)	0.9551 (2)	0.33125 (14)	0.0351 (4)
H8A	0.1298	0.8376	0.3468	0.042*
H8B	0.0810	0.9794	0.2753	0.042*
C9	0.14185 (9)	1.0497 (2)	0.42769 (13)	0.0306 (4)
H9A	0.1427	1.1670	0.4139	0.037*
H9B	0.1053	1.0309	0.4437	0.037*
C10	0.22223 (9)	1.0870 (2)	0.61827 (14)	0.0316 (4)
H10A	0.1855	1.0671	0.6336	0.038*
H10B	0.2252	1.2053	0.6099	0.038*
C11	0.28740 (10)	1.0267 (3)	0.70735 (15)	0.0430 (5)
H11A	0.2967	1.0832	0.7716	0.065*
H11B	0.3238	1.0477	0.6924	0.065*
H11C	0.2842	0.9098	0.7162	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0231 (2)	0.0274 (2)	0.0238 (2)	0.00348 (15)	0.00832 (17)	−0.00108 (15)
O1	0.0244 (6)	0.0241 (6)	0.0319 (6)	0.0018 (5)	0.0131 (5)	−0.0030 (5)
O2	0.0229 (6)	0.0252 (6)	0.0285 (6)	−0.0020 (5)	0.0097 (5)	−0.0005 (5)
O3	0.0373 (8)	0.0698 (10)	0.0298 (7)	0.0153 (7)	0.0174 (6)	0.0157 (7)
N1	0.0237 (7)	0.0218 (7)	0.0246 (7)	0.0019 (5)	0.0126 (6)	0.0006 (5)
C1	0.0239 (8)	0.0234 (8)	0.0194 (7)	0.0006 (6)	0.0107 (7)	0.0047 (6)
C2	0.0239 (8)	0.0194 (7)	0.0243 (8)	0.0022 (6)	0.0128 (7)	0.0051 (6)
C3	0.0234 (8)	0.0231 (8)	0.0243 (8)	0.0029 (6)	0.0118 (7)	0.0039 (6)
C4	0.0237 (9)	0.0377 (10)	0.0326 (9)	0.0040 (8)	0.0105 (8)	−0.0010 (8)
C5	0.0288 (10)	0.0427 (10)	0.0431 (10)	0.0101 (8)	0.0192 (9)	−0.0002 (9)
C6	0.0386 (10)	0.0316 (9)	0.0370 (9)	0.0056 (8)	0.0239 (8)	−0.0013 (8)
C7	0.0307 (9)	0.0239 (8)	0.0261 (8)	−0.0002 (7)	0.0142 (7)	0.0004 (7)
C8	0.0273 (9)	0.0471 (10)	0.0247 (9)	0.0033 (8)	0.0083 (7)	0.0042 (8)
C9	0.0256 (9)	0.0318 (9)	0.0311 (9)	0.0069 (7)	0.0117 (8)	0.0062 (7)
C10	0.0373 (10)	0.0296 (9)	0.0323 (9)	−0.0014 (7)	0.0207 (8)	−0.0073 (7)
C11	0.0356 (11)	0.0634 (13)	0.0266 (9)	−0.0058 (10)	0.0128 (8)	−0.0115 (9)

S1—C3	1.7953 (16)	C5—C6	1.387 (3)
S1—S1i	2.0528 (13)	C5—H5	0.9500
O1—C1	1.2499 (19)	C6—C7	1.378 (2)
O2—C1	1.270 (2)	C6—H6	0.9500
O3—C8	1.411 (2)	C7—H7	0.9500
O3—H3	0.8401	C8—C9	1.509 (3)
N1—C9	1.489 (2)	C8—H8A	0.9900
N1—C10	1.492 (2)	C8—H8B	0.9900
N1—H1A	0.9200	C9—H9A	0.9900
N1—H1B	0.9200	C9—H9B	0.9900
C1—C2	1.502 (2)	C10—C11	1.503 (3)
C2—C7	1.400 (2)	C10—H10A	0.9900
C2—C3	1.407 (2)	C10—H10B	0.9900
C3—C4	1.393 (2)	C11—H11A	0.9800
C4—C5	1.377 (3)	C11—H11B	0.9800
C4—H4	0.9500	C11—H11C	0.9800
C3—S1—S1i	104.39 (6)	C6—C7—H7	119.3
C8—O3—H3	105.1	C2—C7—H7	119.3
C9—N1—C10	114.12 (13)	O3—C8—C9	113.00 (16)
C9—N1—H1A	108.7	O3—C8—H8A	109.0
C10—N1—H1A	108.7	C9—C8—H8A	109.0
C9—N1—H1B	108.7	O3—C8—H8B	109.0
C10—N1—H1B	108.7	C9—C8—H8B	109.0
H1A—N1—H1B	107.6	H8A—C8—H8B	107.8
O1—C1—O2	123.69 (15)	N1—C9—C8	112.07 (14)
O1—C1—C2	118.79 (14)	N1—C9—H9A	109.2
O2—C1—C2	117.52 (14)	C8—C9—H9A	109.2
C7—C2—C3	118.91 (15)	N1—C9—H9B	109.2
C7—C2—C1	118.46 (14)	C8—C9—H9B	109.2
C3—C2—C1	122.62 (14)	H9A—C9—H9B	107.9
C4—C3—C2	118.84 (15)	N1—C10—C11	110.34 (14)
C4—C3—S1	121.51 (13)	N1—C10—H10A	109.6
C2—C3—S1	119.63 (12)	C11—C10—H10A	109.6
C5—C4—C3	121.12 (17)	N1—C10—H10B	109.6
C5—C4—H4	119.4	C11—C10—H10B	109.6
C3—C4—H4	119.4	H10A—C10—H10B	108.1
C4—C5—C6	120.48 (17)	C10—C11—H11A	109.5
C4—C5—H5	119.8	C10—C11—H11B	109.5
C6—C5—H5	119.8	H11A—C11—H11B	109.5
C7—C6—C5	119.15 (16)	C10—C11—H11C	109.5
C7—C6—H6	120.4	H11A—C11—H11C	109.5
C5—C6—H6	120.4	H11B—C11—H11C	109.5
C6—C7—C2	121.48 (16)
O1—C1—C2—C7	153.69 (15)	C2—C3—C4—C5	−1.4 (3)
O2—C1—C2—C7	−26.3 (2)	S1—C3—C4—C5	177.14 (15)
O1—C1—C2—C3	−25.0 (2)	C3—C4—C5—C6	0.9 (3)
O2—C1—C2—C3	155.09 (14)	C4—C5—C6—C7	0.5 (3)
C7—C2—C3—C4	0.6 (2)	C5—C6—C7—C2	−1.3 (3)
C1—C2—C3—C4	179.26 (15)	C3—C2—C7—C6	0.7 (2)
C7—C2—C3—S1	−177.96 (12)	C1—C2—C7—C6	−177.99 (15)
C1—C2—C3—S1	0.7 (2)	C10—N1—C9—C8	−177.21 (14)
S1i—S1—C3—C4	16.34 (15)	O3—C8—C9—N1	−66.5 (2)
S1i—S1—C3—C2	−165.14 (11)	C9—N1—C10—C11	177.61 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.92	1.94	2.840 (2)	164
N1—H1B···O2	0.92	1.85	2.7617 (19)	171
O3—H3···O2ii	0.84	1.92	2.763 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.92	1.94	2.840 (2)	164
N1—H1B⋯O2	0.92	1.85	2.7617 (19)	171
O3—H3⋯O2i	0.84	1.92	2.763 (2)	177

Symmetry code: (i) .