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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2768.
Published online 2009 October 17. doi:  10.1107/S1600536809041415
PMCID: PMC2971119
Copyright © Yang et al. 2009
Tris(tetra­ethyl­ammonium) hydrogen bis­[2-(sulfatosulfan­yl)benzoate]
Yun-Xia Yang,a Qi Li,a and Seik Weng Ngb*
aCollege of Chemistry, Beijing Normal University, Beijing 100875, People’s Republic of China
bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received September 25, 2009; Accepted October 10, 2009.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Abstract
The reaction between tetra­ethyl­ammonium hydroxide and 2,2′-dithio­benzoic acid yields the title compound, 3C8H20N·H(C6H4O5S2)2 3−, 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 [triangle]); Chen et al. (2004 [triangle]).
An external file that holds a picture, illustration, etc. Object name is e-65-o2768-scheme1.jpg Object name is e-65-o2768-scheme1.jpg
Crystal data
  • 3C8H20N+·C6H5O5S2 2−·C6H4O5S2 −
  • M r = 856.20
  • Triclinic, An external file that holds a picture, illustration, etc. Object name is e-65-o2768-efi1.jpg
  • 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 [triangle]) T min = 0.880, T max = 0.949
  • 10538 measured reflections
  • 5176 independent reflections
  • 4013 reflections with I > 2σ(I)
  • R int = 0.016
Refinement
  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041415/xu2617sup1.cif
Click here to view.(23K, cif)
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041415/xu2617Isup2.hkl
Click here to view.(253K, hkl)
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank Beijing Normal University and the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
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.
Experimental
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
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.
Figures
Fig. 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.
Crystal data
3C8H20N+·C6H5O5S22−·C6H4O5S2−Z = 1
Mr = 856.20F(000) = 462
Triclinic, P1Dx = 1.252 Mg m−3
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 mm−1
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
Bruker APEXII diffractometer5176 independent reflections
Radiation source: fine-focus sealed tube4013 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→10
Tmin = 0.880, Tmax = 0.949k = −11→12
10538 measured reflectionsl = −22→22
Refinement
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 = 1.03w = 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 Å−3
62 restraintsΔρmin = −0.28 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
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*
H4B−0.05200.66580.27860.183*
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)
H7A−0.00160.63530.40480.080*
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
H9A0.28090.2935−0.01290.164*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
H10B0.07840.3853−0.03530.309*0.50
H10C0.24250.5553−0.03270.309*0.50
C110.552 (2)0.5441 (12)−0.0741 (5)0.123 (3)0.50
H11A0.67460.6299−0.07350.148*0.50
H11B0.46460.5871−0.09240.148*0.50
C120.539 (2)0.4172 (17)−0.1343 (7)0.143 (5)0.50
H12A0.65730.4138−0.13530.214*0.50
H12B0.50230.4420−0.18550.214*0.50
H12C0.44880.3155−0.12020.214*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)
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, °)
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—C20−179.3 (3)
O5—S1—S2—C23−55.11 (13)C18—C19—C20—C210.3 (5)
O4—S1—S2—C23−173.80 (13)C19—C20—C21—C22−2.0 (5)
C5—N1—C1—C255.0 (3)C20—C21—C22—C232.4 (5)
C7—N1—C1—C2174.6 (3)C21—C22—C23—C18−0.9 (4)
C3—N1—C1—C2−65.3 (3)C21—C22—C23—S2178.8 (2)
C5—N1—C3—C462.1 (4)C19—C18—C23—C22−0.7 (4)
C7—N1—C3—C4−58.2 (4)C17—C18—C23—C22179.7 (3)
C1—N1—C3—C4−176.3 (4)C19—C18—C23—S2179.5 (2)
C7—N1—C5—C6−59.0 (3)C17—C18—C23—S2−0.1 (3)
C3—N1—C5—C6179.3 (3)S1—S2—C23—C22−3.3 (3)
C1—N1—C5—C660.1 (3)S1—S2—C23—C18176.46 (17)
C5—N1—C7—C8−174.2 (3)C15—N2—C9—C1059.8 (16)
C3—N1—C7—C8−53.5 (4)C11—N2—C9—C10−59.9 (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—C19−41.7 (4)C9—N2—C11—C12−70.8 (16)
O1'—C17—C18—C19−137.8 (4)C15—N2—C13—C14−52.6 (15)
O2—C17—C18—C23−39.2 (6)C11—N2—C13—C1471.5 (15)
O2'—C17—C18—C23−139.3 (5)C9—N2—C13—C14−167.1 (13)
O1—C17—C18—C23137.9 (4)C11—N2—C15—C16−172.6 (10)
O1'—C17—C18—C2341.8 (5)C13—N2—C15—C16−44.6 (13)
C23—C18—C19—C201.1 (4)C9—N2—C15—C1664.5 (12)
Hydrogen-bond geometry (Å, °)
D—H···AD—HH···AD···AD—H···A
O1'—H1'···O1i0.821.622.436 (6)175
Symmetry codes: (i) −x+1, −y+2, −z+2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2617).
References
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