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The title compound, C6H4S4+·C9H16NO5S-, which includes an organic diamagnetic anion, was obtained unexpectedly by metathesis of the tetra­phenyl­phospho­nium salt of an organic free-radical anion, 2,2,6,6-tetra­methyl­piperidinyl­oxy-4-hydroxy-4-sulfonate, with (TTF)3(BF4)2 (TTF = tetra­thia­fulvalene).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019032/ob6288sup1.cif
Contains datablocks General, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019032/ob62883sup2.hkl
Contains datablock 3

CCDC reference: 225700

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.067
  • wR factor = 0.042
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ? PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... S5 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN for Windows; software used to prepare material for publication: TEXSAN for Windows.

(3) top
Crystal data top
C6H4S4+·C9H16NO5SZ = 2
Mr = 454.63F(000) = 474.00
Triclinic, P1Dx = 1.548 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.7107 Å
a = 10.884 (1) ÅCell parameters from 25 reflections
b = 12.132 (2) Åθ = 14.1–15.0°
c = 7.948 (1) ŵ = 0.62 mm1
α = 102.78 (1)°T = 296 K
β = 106.02 (1)°Plate, black
γ = 79.52 (1)°0.18 × 0.15 × 0.05 mm
V = 975.5 (3) Å3
Data collection top
Rigaku AFC-7R
diffractometer
2479 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ω–2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 1515
Tmin = 0.950, Tmax = 0.970l = 109
4709 measured reflections3 standard reflections every 150 reflections
4476 independent reflections intensity decay: 0.4%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.067H-atom parameters not refined
wR(F2) = 0.042Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo)]
S = 1.71(Δ/σ)max < 0.001
2479 reflectionsΔρmax = 0.55 e Å3
235 parametersΔρmin = 0.55 e Å3
Special details top

Experimental. The scan width was (1.21 + 0.30tanθ)° with an ω scan speed of 0° per minute (up to 2 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.0352 (1)0.0976 (1)0.3360 (2)0.0339 (4)
S20.1370 (1)0.1126 (1)0.1430 (2)0.0350 (4)
S30.2382 (1)0.0015 (1)0.2362 (2)0.0346 (4)
S40.1318 (1)0.2082 (1)0.0340 (2)0.0354 (4)
S50.4477 (1)0.2049 (1)0.2021 (2)0.0377 (4)
O10.1583 (3)0.6474 (3)0.6652 (5)0.054 (1)
O20.3190 (3)0.2686 (2)0.2749 (4)0.034 (1)
O30.5460 (3)0.2785 (3)0.2682 (5)0.054 (1)
O40.4774 (3)0.1020 (3)0.2748 (5)0.063 (1)
O50.3977 (3)0.1856 (3)0.0132 (5)0.063 (1)
N10.3295 (3)0.3809 (3)0.3862 (5)0.023 (1)
C10.1908 (4)0.0864 (4)0.3336 (6)0.040 (2)
C20.2385 (4)0.0100 (4)0.2466 (6)0.038 (2)
C30.0069 (4)0.0367 (4)0.2167 (6)0.026 (1)
C40.1100 (4)0.0786 (3)0.1702 (6)0.029 (1)
C50.3367 (4)0.1045 (4)0.1300 (7)0.040 (2)
C60.2886 (4)0.1979 (4)0.0371 (6)0.035 (1)
C70.2313 (4)0.5807 (4)0.5914 (6)0.035 (2)
C80.2392 (5)0.5786 (4)0.4068 (7)0.045 (2)
C90.3269 (5)0.4895 (4)0.6763 (6)0.041 (2)
C100.2325 (4)0.4610 (4)0.2856 (6)0.032 (1)
C110.3201 (4)0.3695 (4)0.5644 (6)0.030 (1)
C120.0924 (4)0.4319 (5)0.2293 (7)0.052 (2)
C130.2731 (5)0.4643 (4)0.1201 (6)0.050 (2)
C140.2001 (5)0.3215 (4)0.5702 (7)0.045 (2)
C150.4383 (5)0.2925 (4)0.6424 (7)0.051 (2)
H10.24100.14520.39500.051*
H20.32340.02180.24110.051*
H30.42250.09330.13550.051*
H40.33900.25800.02200.051*
H50.31950.60280.41410.051*
H60.17080.63060.35570.051*
H70.31180.48970.78840.051*
H80.41180.50850.69450.051*
H90.06110.42730.10300.051*
H100.04000.49060.28700.051*
H110.09110.36160.25930.051*
H120.20190.45770.01980.051*
H130.33920.40210.10260.051*
H140.30630.53380.13370.051*
H150.19890.31130.69970.051*
H160.12660.37290.52840.051*
H170.19650.24980.49390.051*
H180.48600.26090.55550.051*
H190.41370.23310.68100.051*
H200.49160.33610.74200.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0328 (8)0.0291 (7)0.0357 (8)0.0021 (6)0.0103 (6)0.0036 (6)
S20.0306 (7)0.0320 (7)0.0444 (9)0.0066 (6)0.0151 (7)0.0012 (6)
S30.0283 (7)0.0339 (8)0.0398 (8)0.0065 (6)0.0103 (6)0.0016 (6)
S40.0349 (8)0.0249 (7)0.0466 (9)0.0019 (6)0.0164 (7)0.0004 (6)
S50.0281 (7)0.0312 (7)0.0541 (9)0.0074 (6)0.0233 (7)0.0111 (6)
O10.051 (2)0.042 (2)0.066 (3)0.007 (2)0.034 (2)0.022 (2)
O20.024 (2)0.029 (2)0.049 (2)0.006 (1)0.018 (2)0.011 (2)
O30.032 (2)0.044 (2)0.088 (3)0.018 (2)0.034 (2)0.017 (2)
O40.054 (3)0.034 (2)0.111 (3)0.010 (2)0.043 (2)0.016 (2)
O50.050 (2)0.085 (3)0.045 (2)0.009 (2)0.024 (2)0.021 (2)
N10.027 (2)0.017 (2)0.026 (2)0.004 (2)0.011 (2)0.005 (2)
C10.034 (3)0.045 (3)0.041 (3)0.002 (3)0.019 (3)0.004 (3)
C20.030 (3)0.049 (3)0.037 (3)0.001 (3)0.013 (2)0.012 (3)
C30.025 (3)0.029 (3)0.023 (3)0.002 (2)0.008 (2)0.004 (2)
C40.032 (3)0.026 (3)0.029 (3)0.007 (2)0.006 (2)0.002 (2)
C50.029 (3)0.040 (3)0.053 (4)0.002 (2)0.016 (3)0.006 (3)
C60.033 (3)0.027 (3)0.044 (3)0.005 (2)0.012 (3)0.008 (2)
C70.033 (3)0.030 (3)0.043 (3)0.014 (2)0.016 (3)0.005 (2)
C80.052 (4)0.033 (3)0.049 (4)0.007 (3)0.017 (3)0.011 (3)
C90.053 (4)0.040 (3)0.031 (3)0.007 (3)0.018 (3)0.003 (2)
C100.034 (3)0.033 (3)0.025 (3)0.001 (2)0.006 (2)0.004 (2)
C110.030 (3)0.032 (3)0.027 (3)0.003 (2)0.007 (2)0.003 (2)
C120.029 (3)0.069 (4)0.051 (4)0.006 (3)0.004 (3)0.009 (3)
C130.060 (4)0.061 (4)0.029 (3)0.001 (3)0.011 (3)0.017 (3)
C140.054 (4)0.041 (3)0.053 (4)0.015 (3)0.030 (3)0.007 (3)
C150.053 (4)0.052 (4)0.045 (4)0.005 (3)0.013 (3)0.015 (3)
Geometric parameters (Å, º) top
S1—C11.718 (6)C7—C91.512 (8)
S1—C31.716 (5)C8—C101.536 (8)
S2—C21.730 (6)C8—H50.95
S2—C31.724 (5)C8—H60.94
S3—C41.717 (5)C9—C111.532 (7)
S3—C51.723 (6)C9—H70.95
S4—C41.719 (5)C9—H80.96
S4—C61.726 (6)C10—C121.549 (8)
S5—O21.659 (4)C10—C131.510 (8)
S5—O31.430 (4)C11—C141.539 (8)
S5—O41.437 (5)C11—C151.514 (8)
S5—O51.430 (5)C12—H90.96
O1—C71.201 (6)C12—H100.95
O2—N11.456 (5)C12—H110.94
N1—C101.484 (7)C13—H120.95
N1—C111.485 (7)C13—H130.96
C1—C21.334 (8)C13—H140.95
C1—H10.95C14—H151.07
C2—H20.95C14—H160.95
C3—C41.398 (7)C14—H170.95
C5—C61.318 (8)C15—H180.95
C5—H30.96C15—H190.95
C6—H40.95C15—H200.96
C7—C81.487 (8)
S1···O1i3.141 (5)O3···C1viii3.346 (7)
S1···S4ii3.329 (2)O3···C8vi3.362 (8)
S1···C3iii3.678 (6)O4···C53.015 (8)
S2···O5ii2.976 (5)O4···C2viii3.190 (7)
S2···S3ii3.416 (3)O4···C1viii3.486 (7)
S2···O2ii3.673 (4)O5···C2ii3.036 (8)
S3···O43.005 (5)O5···C5vii3.303 (7)
S3···O23.473 (4)O5···C6vii3.579 (7)
S4···O1iv3.123 (4)O5···C15ix3.631 (8)
O1···C6v3.235 (7)C1···C6ii3.339 (9)
O1···C1i3.310 (8)C1···C5ii3.625 (9)
O1···O3vi3.369 (5)C2···C5ii3.40 (1)
O1···C12i3.413 (8)C2···C6ii3.617 (9)
O3···C7vi3.034 (7)C3···C4ii3.479 (8)
O3···C9vi3.250 (7)C5···C15x3.439 (9)
O3···C6vii3.287 (7)C6···C15x3.538 (9)
C1—S1—C395.1 (3)C7—C9—H7108.5
C2—S2—C395.3 (3)C7—C9—H8108.1
C4—S3—C594.7 (3)C11—C9—H7109.1
C4—S4—C694.7 (3)C11—C9—H8108.2
O2—S5—O3108.5 (2)H7—C9—H8108.9
O2—S5—O4101.8 (2)N1—C10—C8105.8 (5)
O2—S5—O5102.4 (2)N1—C10—C12115.5 (5)
O3—S5—O4114.2 (3)N1—C10—C13108.2 (5)
O3—S5—O5115.1 (3)C8—C10—C12110.0 (5)
O4—S5—O5113.0 (3)C8—C10—C13108.7 (5)
S5—O2—N1116.3 (3)C12—C10—C13108.4 (5)
O2—N1—C10105.8 (4)N1—C11—C9105.0 (5)
O2—N1—C11106.3 (4)N1—C11—C14116.5 (5)
C10—N1—C11119.6 (4)N1—C11—C15107.8 (5)
S1—C1—C2117.9 (5)C9—C11—C14110.8 (5)
S1—C1—H1121.7C9—C11—C15108.3 (5)
C2—C1—H1120.3C14—C11—C15108.1 (5)
S2—C2—C1116.3 (5)C10—C12—H9108.7
S2—C2—H2121.6C10—C12—H10109.2
C1—C2—H2122.1C10—C12—H11109.5
S1—C3—S2115.2 (3)H9—C12—H10109.0
S1—C3—C4122.5 (4)H9—C12—H11109.6
S2—C3—C4122.1 (4)H10—C12—H11110.8
S3—C4—S4115.7 (3)C10—C13—H12110.1
S3—C4—C3122.4 (4)C10—C13—H13109.1
S4—C4—C3121.9 (4)C10—C13—H14109.8
S3—C5—C6117.7 (5)H12—C13—H13109.1
S3—C5—H3121.2H12—C13—H14109.9
C6—C5—H3121.1H13—C13—H14108.9
S4—C6—C5117.2 (5)C11—C14—H15114.2
S4—C6—H4121.5C11—C14—H16107.7
C5—C6—H4121.3C11—C14—H17108.1
O1—C7—C8124.2 (6)H15—C14—H16108.3
O1—C7—C9123.8 (6)H15—C14—H17108.6
C8—C7—C9112.1 (5)H16—C14—H17109.9
C7—C8—C10114.5 (5)C11—C15—H18109.8
C7—C8—H5107.7C11—C15—H19110.2
C7—C8—H6108.2C11—C15—H20109.3
C10—C8—H5108.1H18—C15—H19109.7
C10—C8—H6108.9H18—C15—H20108.9
H5—C8—H6109.5H19—C15—H20109.0
C7—C9—C11114.0 (5)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z; (iii) x, y, z+1; (iv) x, y1, z1; (v) x, y+1, z+1; (vi) x+1, y+1, z+1; (vii) x+1, y, z; (viii) x+1, y, z; (ix) x, y, z1; (x) x+1, y, z+1.
 

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