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

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ISSN: 2056-9890

Tris(tetra­ethyl­ammonium) hydrogen bis­­[2-(sulfatosulfan­yl)benzoate]

aCollege of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 25 September 2009; accepted 10 October 2009; online 17 October 2009)

The reaction between tetra­ethyl­ammonium hydroxide and 2,2′-dithio­benzoic acid yields the title compound, 3C8H20N·H(C6H4O5S2)23−, the trianion of which comprises two 2-(sulfato­sulfan­yl)benzoate dianions linked across a center of inversion by an acid H atom. One of the cations is disordered about another center of inversion.

Related literature

For the crystal structures of other aryl­thio­sulfates, see: Boese et al. (1999[Boese, R., Graw, M., Haas, A., Carl Krüger, C., Mönicke, A. & Schlagheck, J. (1999). Z. Anorg. Allg. Chem. 625, 1261-1272.]); Chen et al. (2004[Chen, J.-X., Xu, Q.-F., Zhang, Y., Zain, S. M., Ng, S. W. & Lang, J.-P. (2004). Acta Cryst. C60, o572-o574.]).

[Scheme 1]

Experimental

Crystal data
  • 3C8H20N+·C6H5O5S22−·C6H4O5S2

  • Mr = 856.20

  • Triclinic, [P \overline 1]

  • a = 7.9774 (1) Å

  • b = 9.2439 (1) Å

  • c = 17.0074 (3) Å

  • α = 90.649 (1)°

  • β = 93.845 (1)°

  • γ = 114.678 (1)°

  • V = 1135.98 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.50 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.880, Tmax = 0.949

  • 10538 measured reflections

  • 5176 independent reflections

  • 4013 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.181

  • S = 1.03

  • 5176 reflections

  • 315 parameters

  • 62 restraints

  • H-atom parameters constrained

  • Δρmax = 0.96 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

The title salt (Fig. 1, Scheme I) was isolated as the product of an attempted hydrolysis of 2,2'-dithiobenzoic acid with tetraethylammonium hydroxide in which an S–Caryl bond was cleaved and the free sulfuryl end then oxidized to a sulfonate group.

Related literature top

For the crystal structures of other arylthiosulfates, see: Boese et al. (1999); Chen et al. (2004).

Experimental top

2,2'-Dithiobenzoic acid (0.25 mmol, 0.08 g) was dissolved in a water-ethanol (1:2 v/v) mixture. A 25% solution of tetraethylammonium hydroxide was added to neutralize the acid and give a yellow coloration to the solution. Yellow blocks separated after several weeks.

Refinement top

One of the two cations is disordered about a center-of-inversion. The cation was allowed to refine off the special position, and with distance restraints of N–C = C–C = 1.50±0.01 Å and N···C = 2.35±0.01 Å. Their anisotropic temperature factors were restrained to be nearly isotropic.

The two carboxyl oxygen atoms of the anion is disordered over two positions; the occupancy disorder refined to nearly 1:1 and as such, the occupancy of the four oxygen atoms was set as 0.5. One 'acid' hydrogen atom was arbitrarily placed on one of the two carboxyl –CO2 components.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The acid H-atom was similar treated.

Structure description top

The title salt (Fig. 1, Scheme I) was isolated as the product of an attempted hydrolysis of 2,2'-dithiobenzoic acid with tetraethylammonium hydroxide in which an S–Caryl bond was cleaved and the free sulfuryl end then oxidized to a sulfonate group.

For the crystal structures of other arylthiosulfates, see: Boese et al. (1999); Chen et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of 3[(C2H5)4N]+ [H(C6H4O5S2)2]3- at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The dashed line denotes a hydrogen bond.
Tris(tetraethylammonium) hydrogen bis[2-(sulfatosulfanyl)benzoate] top
Crystal data top
3C8H20N+·C6H5O5S22·C6H4O5S2Z = 1
Mr = 856.20F(000) = 462
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9774 (1) ÅCell parameters from 4127 reflections
b = 9.2439 (1) Åθ = 2.2–28.2°
c = 17.0074 (3) ŵ = 0.26 mm1
α = 90.649 (1)°T = 293 K
β = 93.845 (1)°Block, yellow
γ = 114.678 (1)°0.50 × 0.20 × 0.20 mm
V = 1135.98 (3) Å3
Data collection top
Bruker APEXII
diffractometer
5176 independent reflections
Radiation source: fine-focus sealed tube4013 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 810
Tmin = 0.880, Tmax = 0.949k = 1112
10538 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1007P)2 + 0.4839P]
where P = (Fo2 + 2Fc2)/3
5176 reflections(Δ/σ)max = 0.001
315 parametersΔρmax = 0.96 e Å3
62 restraintsΔρmin = 0.28 e Å3
Crystal data top
3C8H20N+·C6H5O5S22·C6H4O5S2γ = 114.678 (1)°
Mr = 856.20V = 1135.98 (3) Å3
Triclinic, P1Z = 1
a = 7.9774 (1) ÅMo Kα radiation
b = 9.2439 (1) ŵ = 0.26 mm1
c = 17.0074 (3) ÅT = 293 K
α = 90.649 (1)°0.50 × 0.20 × 0.20 mm
β = 93.845 (1)°
Data collection top
Bruker APEXII
diffractometer
5176 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4013 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.949Rint = 0.016
10538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05862 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.03Δρmax = 0.96 e Å3
5176 reflectionsΔρmin = 0.28 e Å3
315 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.37903 (8)0.68955 (7)0.65535 (4)0.04844 (19)
S20.44246 (9)0.81719 (10)0.76485 (4)0.0641 (2)
O10.6914 (7)1.0046 (7)0.9874 (2)0.0780 (13)0.50
O20.5551 (8)1.0673 (8)0.8853 (3)0.0895 (16)0.50
O1'0.4910 (7)0.9213 (7)0.9244 (3)0.0896 (15)0.50
H1'0.42990.95010.95240.134*0.50
O2'0.7394 (9)1.1516 (7)0.9423 (4)0.123 (2)0.50
O30.3824 (3)0.5381 (2)0.66859 (14)0.0691 (5)
O40.1964 (3)0.6831 (3)0.63761 (13)0.0711 (6)
O50.5132 (3)0.7840 (2)0.60344 (11)0.0626 (5)
N10.2613 (3)0.7183 (2)0.37055 (12)0.0483 (5)
C10.4500 (4)0.8384 (3)0.4057 (2)0.0648 (7)
H1A0.45150.94380.40490.078*
H1B0.46500.81490.46050.078*
C20.6126 (4)0.8418 (4)0.3648 (3)0.0862 (11)
H2A0.72420.92500.38860.129*
H2B0.59770.86160.31000.129*
H2C0.61970.74110.36950.129*
C30.2295 (5)0.7693 (4)0.2883 (2)0.0802 (10)
H3A0.24440.87880.29210.096*
H3B0.32460.76660.25640.096*
C40.0438 (6)0.6697 (6)0.2463 (3)0.1221 (19)
H4A0.03160.71600.19720.183*
H4B0.05200.66580.27860.183*
H4C0.03310.56370.23620.183*
C50.2520 (4)0.5528 (3)0.36561 (16)0.0577 (6)
H5A0.13130.48170.34140.069*
H5B0.34370.55230.33110.069*
C60.2829 (5)0.4878 (4)0.44214 (18)0.0700 (8)
H6A0.28310.38530.43280.105*
H6B0.18560.47720.47510.105*
H6C0.39980.55900.46790.105*
C70.1166 (4)0.7199 (4)0.4235 (2)0.0670 (7)
H7A0.00160.63530.40480.080*
H7B0.14790.69510.47620.080*
C80.0934 (6)0.8724 (5)0.4290 (3)0.1058 (15)
H8A0.00170.86180.46500.159*
H8B0.05460.89540.37780.159*
H8C0.20920.95770.44760.159*
C170.6587 (4)1.0166 (3)0.91364 (15)0.0567 (6)
C180.7597 (3)0.9504 (3)0.86229 (13)0.0460 (5)
C190.9423 (4)0.9817 (4)0.88510 (17)0.0644 (7)
H190.99741.04160.93160.077*
C201.0444 (4)0.9273 (4)0.8414 (2)0.0723 (8)
H201.16640.94960.85820.087*
C210.9646 (4)0.8399 (4)0.77289 (19)0.0692 (8)
H211.03380.80530.74200.083*
C220.7832 (4)0.8030 (4)0.74946 (17)0.0616 (7)
H220.72960.74000.70370.074*
C230.6766 (3)0.8578 (3)0.79291 (14)0.0459 (5)
N20.5156 (17)0.4964 (13)0.0090 (6)0.068 (2)0.50
C90.3158 (14)0.3911 (13)0.0188 (9)0.137 (4)0.50
H9A0.28090.29350.01290.164*0.50
H9B0.30390.36260.07350.164*0.50
C100.182 (3)0.462 (3)0.0034 (13)0.206 (8)0.50
H10A0.14010.49000.04340.309*0.50
H10B0.07840.38530.03530.309*0.50
H10C0.24250.55530.03270.309*0.50
C110.552 (2)0.5441 (12)0.0741 (5)0.123 (3)0.50
H11A0.67460.62990.07350.148*0.50
H11B0.46460.58710.09240.148*0.50
C120.539 (2)0.4172 (17)0.1343 (7)0.143 (5)0.50
H12A0.65730.41380.13530.214*0.50
H12B0.50230.44200.18550.214*0.50
H12C0.44880.31550.12020.214*0.50
C130.6031 (14)0.3908 (11)0.0405 (6)0.107 (3)0.50
H13A0.54830.34710.08890.129*0.50
H13B0.57230.30230.00270.129*0.50
C140.8051 (18)0.467 (2)0.0567 (13)0.198 (8)0.50
H14A0.86190.50930.00910.298*0.50
H14B0.84770.39050.07600.298*0.50
H14C0.83780.55270.09570.298*0.50
C150.5711 (13)0.6447 (9)0.0597 (4)0.092 (2)0.50
H15A0.69540.71760.04890.110*0.50
H15B0.48940.69500.04440.110*0.50
C160.5675 (16)0.6226 (15)0.1450 (5)0.101 (3)0.50
H16A0.44290.55860.15730.152*0.50
H16B0.61210.72460.17250.152*0.50
H16C0.64500.57020.16090.152*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0447 (3)0.0460 (3)0.0508 (3)0.0161 (2)0.0003 (2)0.0046 (2)
S20.0499 (4)0.0960 (6)0.0557 (4)0.0415 (4)0.0034 (3)0.0234 (3)
O10.097 (3)0.122 (4)0.0400 (19)0.072 (3)0.0035 (19)0.007 (2)
O20.121 (4)0.140 (5)0.058 (2)0.105 (4)0.004 (3)0.009 (3)
O1'0.080 (3)0.124 (4)0.071 (3)0.050 (3)0.014 (2)0.035 (3)
O2'0.130 (5)0.074 (3)0.155 (6)0.029 (3)0.050 (4)0.044 (4)
O30.0688 (12)0.0459 (10)0.0923 (15)0.0231 (9)0.0119 (11)0.0035 (9)
O40.0524 (11)0.0802 (14)0.0776 (13)0.0281 (10)0.0143 (9)0.0158 (11)
O50.0668 (12)0.0628 (11)0.0528 (10)0.0211 (9)0.0102 (9)0.0050 (8)
N10.0435 (10)0.0453 (10)0.0535 (11)0.0158 (8)0.0049 (8)0.0067 (8)
C10.0514 (15)0.0519 (15)0.0835 (19)0.0159 (12)0.0037 (13)0.0059 (13)
C20.0452 (15)0.078 (2)0.133 (3)0.0238 (15)0.0088 (17)0.000 (2)
C30.0696 (19)0.083 (2)0.075 (2)0.0187 (16)0.0019 (15)0.0304 (17)
C40.093 (3)0.132 (4)0.094 (3)0.005 (3)0.032 (2)0.049 (3)
C50.0614 (15)0.0504 (14)0.0593 (15)0.0212 (12)0.0077 (12)0.0036 (11)
C60.091 (2)0.0666 (17)0.0684 (18)0.0484 (17)0.0055 (16)0.0087 (14)
C70.0561 (16)0.0599 (16)0.089 (2)0.0262 (13)0.0178 (14)0.0033 (14)
C80.081 (2)0.079 (2)0.177 (4)0.048 (2)0.043 (3)0.011 (3)
C170.0716 (18)0.0591 (15)0.0453 (13)0.0331 (14)0.0073 (12)0.0049 (11)
C180.0551 (13)0.0469 (12)0.0403 (11)0.0251 (10)0.0063 (9)0.0021 (9)
C190.0577 (16)0.0710 (18)0.0563 (15)0.0214 (13)0.0099 (12)0.0125 (13)
C200.0465 (15)0.086 (2)0.085 (2)0.0300 (15)0.0087 (14)0.0126 (17)
C210.0523 (15)0.085 (2)0.081 (2)0.0394 (15)0.0037 (14)0.0147 (16)
C220.0560 (15)0.0758 (18)0.0602 (15)0.0365 (14)0.0032 (12)0.0226 (13)
C230.0435 (11)0.0532 (13)0.0450 (12)0.0245 (10)0.0016 (9)0.0021 (10)
N20.090 (4)0.049 (2)0.063 (5)0.026 (2)0.016 (4)0.011 (3)
C90.115 (7)0.104 (6)0.181 (8)0.036 (5)0.002 (6)0.005 (6)
C100.182 (11)0.226 (12)0.227 (12)0.106 (9)0.002 (8)0.015 (9)
C110.185 (8)0.101 (6)0.086 (5)0.062 (6)0.021 (5)0.015 (4)
C120.196 (10)0.140 (8)0.097 (7)0.073 (7)0.028 (7)0.000 (6)
C130.127 (6)0.098 (5)0.113 (6)0.060 (5)0.025 (5)0.012 (4)
C140.192 (11)0.198 (11)0.214 (12)0.092 (8)0.007 (8)0.006 (8)
C150.116 (5)0.073 (4)0.086 (4)0.039 (4)0.014 (4)0.003 (3)
C160.109 (6)0.106 (6)0.082 (5)0.040 (5)0.002 (5)0.007 (4)
Geometric parameters (Å, º) top
S1—O31.432 (2)C18—C191.387 (4)
S1—O51.4325 (19)C18—C231.401 (3)
S1—O41.444 (2)C19—C201.373 (4)
S1—S22.1075 (9)C19—H190.9300
S2—C231.774 (2)C20—C211.365 (4)
O1—C171.280 (5)C20—H200.9300
O2—C171.188 (5)C21—C221.370 (4)
O1'—C171.285 (6)C21—H210.9300
O1'—H1'0.8200C22—C231.400 (3)
O2'—C171.217 (6)C22—H220.9300
N1—C51.502 (3)N2—C151.495 (9)
N1—C71.515 (3)N2—C111.497 (9)
N1—C31.521 (4)N2—C131.502 (9)
N1—C11.525 (3)N2—C91.503 (10)
C1—C21.502 (5)C9—C101.496 (9)
C1—H1A0.9700C9—H9A0.9700
C1—H1B0.9700C9—H9B0.9700
C2—H2A0.9600C10—H10A0.9600
C2—H2B0.9600C10—H10B0.9600
C2—H2C0.9600C10—H10C0.9600
C3—C41.502 (5)C11—C121.513 (9)
C3—H3A0.9700C11—H11A0.9700
C3—H3B0.9700C11—H11B0.9700
C4—H4A0.9600C12—H12A0.9600
C4—H4B0.9600C12—H12B0.9600
C4—H4C0.9600C12—H12C0.9600
C5—C61.488 (4)C13—C141.469 (9)
C5—H5A0.9700C13—H13A0.9700
C5—H5B0.9700C13—H13B0.9700
C6—H6A0.9600C14—H14A0.9600
C6—H6B0.9600C14—H14B0.9600
C6—H6C0.9600C14—H14C0.9600
C7—C81.500 (4)C15—C161.467 (8)
C7—H7A0.9700C15—H15A0.9700
C7—H7B0.9700C15—H15B0.9700
C8—H8A0.9600C16—H16A0.9600
C8—H8B0.9600C16—H16B0.9600
C8—H8C0.9600C16—H16C0.9600
C17—C181.511 (3)
O3—S1—O5113.19 (13)H8A—C8—H8C109.5
O3—S1—O4114.49 (13)H8B—C8—H8C109.5
O5—S1—O4114.26 (13)O2—C17—O2'83.1 (5)
O3—S1—S2107.77 (10)O2—C17—O1125.9 (3)
O5—S1—S2107.23 (9)O2'—C17—O173.1 (5)
O4—S1—S298.34 (9)O2—C17—O1'69.9 (4)
C23—S2—S1105.73 (8)O2'—C17—O1'125.1 (4)
C17—O1'—H1'120.0O1—C17—O1'85.3 (4)
C5—N1—C7108.87 (19)O2—C17—C18120.9 (3)
C5—N1—C3109.5 (2)O2'—C17—C18119.3 (4)
C7—N1—C3111.1 (2)O1—C17—C18113.1 (3)
C5—N1—C1111.6 (2)O1'—C17—C18115.6 (3)
C7—N1—C1108.0 (2)C19—C18—C23118.6 (2)
C3—N1—C1107.8 (2)C19—C18—C17118.6 (2)
C2—C1—N1115.2 (3)C23—C18—C17122.8 (2)
C2—C1—H1A108.5C20—C19—C18122.2 (3)
N1—C1—H1A108.5C20—C19—H19118.9
C2—C1—H1B108.5C18—C19—H19118.9
N1—C1—H1B108.5C21—C20—C19119.2 (3)
H1A—C1—H1B107.5C21—C20—H20120.4
C1—C2—H2A109.5C19—C20—H20120.4
C1—C2—H2B109.5C20—C21—C22120.3 (3)
H2A—C2—H2B109.5C20—C21—H21119.8
C1—C2—H2C109.5C22—C21—H21119.8
H2A—C2—H2C109.5C21—C22—C23121.5 (2)
H2B—C2—H2C109.5C21—C22—H22119.3
C4—C3—N1115.2 (3)C23—C22—H22119.3
C4—C3—H3A108.5C22—C23—C18118.2 (2)
N1—C3—H3A108.5C22—C23—S2123.68 (19)
C4—C3—H3B108.5C18—C23—S2118.15 (17)
N1—C3—H3B108.5C15—N2—C11108.0 (8)
H3A—C3—H3B107.5C15—N2—C13112.0 (9)
C3—C4—H4A109.5C11—N2—C13115.3 (10)
C3—C4—H4B109.5C15—N2—C9108.4 (10)
H4A—C4—H4B109.5C11—N2—C9113.1 (10)
C3—C4—H4C109.5C13—N2—C999.7 (9)
H4A—C4—H4C109.5C10—C9—N2115.5 (12)
H4B—C4—H4C109.5C10—C9—H9A108.4
C6—C5—N1115.4 (2)N2—C9—H9A108.4
C6—C5—H5A108.4C10—C9—H9B108.4
N1—C5—H5A108.4N2—C9—H9B108.4
C6—C5—H5B108.4H9A—C9—H9B107.5
N1—C5—H5B108.4N2—C11—C12117.8 (9)
H5A—C5—H5B107.5N2—C11—H11A107.9
C5—C6—H6A109.5C12—C11—H11A107.9
C5—C6—H6B109.5N2—C11—H11B107.9
H6A—C6—H6B109.5C12—C11—H11B107.9
C5—C6—H6C109.5H11A—C11—H11B107.2
H6A—C6—H6C109.5C14—C13—N2115.8 (11)
H6B—C6—H6C109.5C14—C13—H13A108.3
C8—C7—N1116.2 (3)N2—C13—H13A108.3
C8—C7—H7A108.2C14—C13—H13B108.3
N1—C7—H7A108.2N2—C13—H13B108.3
C8—C7—H7B108.2H13A—C13—H13B107.4
N1—C7—H7B108.2C16—C15—N2115.7 (8)
H7A—C7—H7B107.4C16—C15—H15A108.4
C7—C8—H8A109.5N2—C15—H15A108.4
C7—C8—H8B109.5C16—C15—H15B108.4
H8A—C8—H8B109.5N2—C15—H15B108.4
C7—C8—H8C109.5H15A—C15—H15B107.4
O3—S1—S2—C2367.06 (13)C17—C18—C19—C20179.3 (3)
O5—S1—S2—C2355.11 (13)C18—C19—C20—C210.3 (5)
O4—S1—S2—C23173.80 (13)C19—C20—C21—C222.0 (5)
C5—N1—C1—C255.0 (3)C20—C21—C22—C232.4 (5)
C7—N1—C1—C2174.6 (3)C21—C22—C23—C180.9 (4)
C3—N1—C1—C265.3 (3)C21—C22—C23—S2178.8 (2)
C5—N1—C3—C462.1 (4)C19—C18—C23—C220.7 (4)
C7—N1—C3—C458.2 (4)C17—C18—C23—C22179.7 (3)
C1—N1—C3—C4176.3 (4)C19—C18—C23—S2179.5 (2)
C7—N1—C5—C659.0 (3)C17—C18—C23—S20.1 (3)
C3—N1—C5—C6179.3 (3)S1—S2—C23—C223.3 (3)
C1—N1—C5—C660.1 (3)S1—S2—C23—C18176.46 (17)
C5—N1—C7—C8174.2 (3)C15—N2—C9—C1059.8 (16)
C3—N1—C7—C853.5 (4)C11—N2—C9—C1059.9 (17)
C1—N1—C7—C864.5 (4)C13—N2—C9—C10177.1 (14)
O2—C17—C18—C19141.2 (5)C15—N2—C11—C12169.3 (12)
O2'—C17—C18—C1941.1 (6)C13—N2—C11—C1243.1 (17)
O1—C17—C18—C1941.7 (4)C9—N2—C11—C1270.8 (16)
O1'—C17—C18—C19137.8 (4)C15—N2—C13—C1452.6 (15)
O2—C17—C18—C2339.2 (6)C11—N2—C13—C1471.5 (15)
O2'—C17—C18—C23139.3 (5)C9—N2—C13—C14167.1 (13)
O1—C17—C18—C23137.9 (4)C11—N2—C15—C16172.6 (10)
O1'—C17—C18—C2341.8 (5)C13—N2—C15—C1644.6 (13)
C23—C18—C19—C201.1 (4)C9—N2—C15—C1664.5 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.821.622.436 (6)175
Symmetry code: (i) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formula3C8H20N+·C6H5O5S22·C6H4O5S2
Mr856.20
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.9774 (1), 9.2439 (1), 17.0074 (3)
α, β, γ (°)90.649 (1), 93.845 (1), 114.678 (1)
V3)1135.98 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.50 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.880, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
10538, 5176, 4013
Rint0.016
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.181, 1.03
No. of reflections5176
No. of parameters315
No. of restraints62
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.96, 0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank Beijing Normal University and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBoese, R., Graw, M., Haas, A., Carl Krüger, C., Mönicke, A. & Schlagheck, J. (1999). Z. Anorg. Allg. Chem. 625, 1261–1272.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, J.-X., Xu, Q.-F., Zhang, Y., Zain, S. M., Ng, S. W. & Lang, J.-P. (2004). Acta Cryst. C60, o572–o574.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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