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The cation and anion of C10H10N22+·C10H6O6S22-·2H2O lie on different twofold rotation axes in the crystal structure. The cations, anions and water mol­ecules are connected by hydrogen bonds into a three-dimensional network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004064/bt6412sup1.cif
Contains datablocks I, sad

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004064/bt6412Isup2.hkl
Contains datablock I

CCDC reference: 236111

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.134
  • Data-to-parameter ratio = 14.6

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 ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07 PLAT432_ALERT_2_C Short Inter X...Y Contact O1W .. C10 .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT736_ALERT_1_C H...A Calc 2.00(3), Rep 2.000(10) ...... 3.00 su-Rat H1# -O1 1.555 1.555
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 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

4,4'-Bipyridinium 1,5-naphthalenedisulfonate dihydrate top
Crystal data top
C10H10N2·C10H6O6S2·2H2OF(000) = 500
Mr = 480.50Dx = 1.572 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 1542 reflections
a = 9.8121 (9) Åθ = 2.7–27.1°
b = 6.6775 (6) ŵ = 0.32 mm1
c = 15.647 (1) ÅT = 298 K
β = 97.957 (2)°Plate, colorless
V = 1015.3 (2) Å30.27 × 0.13 × 0.08 mm
Z = 2
Data collection top
Bruker SMART APEX area-detector
diffractometer
1860 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
φ and ω scanh = 125
5865 measured reflectionsk = 88
2296 independent reflectionsl = 2020
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0721P)2 + 0.203P]
where P = (Fo2 + 2Fc2)/3
2296 reflections(Δ/σ)max = 0.001
157 parametersΔρmax = 0.23 e Å3
3 restraintsΔρmin = 0.40 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.75151 (5)0.63522 (8)0.61589 (3)0.0323 (2)
O10.7097 (2)0.4480 (3)0.5733 (1)0.0457 (4)
O20.6972 (2)0.8078 (3)0.5656 (1)0.0493 (5)
O30.8980 (2)0.6489 (3)0.6413 (1)0.0505 (5)
O1w0.5272 (2)0.1319 (3)0.5991 (1)0.0510 (5)
N10.2441 (2)0.1582 (3)0.6095 (1)0.0434 (5)
C10.6736 (2)0.6384 (3)0.7126 (1)0.0282 (4)
C20.7594 (2)0.6403 (3)0.7893 (1)0.0316 (5)
C30.7042 (2)0.6389 (3)0.8677 (1)0.0326 (5)
C40.5662 (2)0.6370 (3)0.8682 (1)0.0308 (5)
C50.4729 (2)0.6378 (3)0.7901 (1)0.0268 (4)
C60.1137 (3)0.1892 (4)0.5782 (2)0.0479 (6)
C70.0137 (2)0.1895 (4)0.6318 (1)0.0431 (6)
C80.0519 (2)0.1569 (3)0.7199 (1)0.0305 (5)
C90.1893 (2)0.1253 (3)0.7497 (2)0.0395 (5)
C100.2847 (3)0.1271 (3)0.6927 (2)0.0463 (6)
H1w10.571 (3)0.238 (3)0.591 (2)0.08 (1)*
H1w20.574 (3)0.033 (3)0.587 (2)0.08 (1)*
H1n0.306 (2)0.154 (3)0.576 (2)0.05 (1)*
H20.85430.64260.78970.038*
H30.76310.63930.91970.039*
H40.53180.63510.92070.037*
H60.08930.21100.51940.057*
H70.07800.21110.60960.052*
H90.21750.10280.80820.047*
H100.37740.10650.71270.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0307 (3)0.0440 (3)0.0249 (3)0.0036 (2)0.0132 (2)0.0018 (2)
O10.052 (1)0.054 (1)0.036 (1)0.002 (1)0.019 (1)0.011 (1)
O20.057 (1)0.057 (1)0.040 (1)0.017 (1)0.029 (1)0.018 (1)
O30.030 (1)0.083 (1)0.042 (1)0.000 (1)0.015 (1)0.002 (1)
O1w0.037 (1)0.054 (1)0.066 (1)0.004 (1)0.018 (1)0.000 (1)
N10.047 (1)0.042 (1)0.049 (1)0.001 (1)0.032 (1)0.002 (1)
C10.030 (1)0.032 (1)0.025 (1)0.001 (1)0.011 (1)0.001 (1)
C20.028 (1)0.038 (1)0.030 (1)0.001 (1)0.005 (1)0.002 (1)
C30.034 (1)0.040 (1)0.023 (1)0.001 (1)0.002 (1)0.002 (1)
C40.033 (1)0.041 (1)0.020 (1)0.001 (1)0.008 (1)0.001 (1)
C50.030 (1)0.031 (1)0.022 (1)0.000 (1)0.009 (1)0.000 (1)
C60.053 (2)0.062 (2)0.032 (1)0.001 (1)0.018 (1)0.004 (1)
C70.037 (1)0.062 (2)0.032 (1)0.002 (1)0.012 (1)0.005 (1)
C80.032 (1)0.032 (1)0.030 (1)0.001 (1)0.013 (1)0.002 (1)
C90.035 (1)0.047 (1)0.039 (1)0.003 (1)0.011 (1)0.002 (1)
C100.033 (1)0.052 (2)0.057 (2)0.003 (1)0.017 (1)0.000 (1)
Geometric parameters (Å, º) top
S1—O11.449 (2)C8—C91.381 (3)
S1—O21.454 (2)C8—C8ii1.480 (4)
S1—O31.440 (2)C9—C101.380 (3)
S1—C11.787 (2)O1w—H1w10.85 (1)
N1—C61.321 (3)O1w—H1w20.84 (1)
N1—C101.325 (3)N1—H1n0.86 (1)
C1—C21.367 (3)C2—H20.93
C1—C5i1.433 (3)C3—H30.93
C2—C31.408 (3)C4—H40.93
C3—C41.356 (3)C6—H60.93
C4—C51.422 (3)C7—H70.93
C5—C5i1.430 (4)C9—H90.93
C6—C71.376 (3)C10—H100.93
C7—C81.394 (3)
O1—S1—O2112.1 (1)C7—C8—C8ii121.0 (3)
O1—S1—O3113.0 (1)C10—C9—C8119.9 (2)
O2—S1—O3112.1 (1)N1—C10—C9119.9 (2)
O1—S1—C1105.8 (1)H1w1—O1w—H1w2109 (3)
O2—S1—C1106.3 (1)C6—N1—H1n120 (2)
O3—S1—C1107.0 (1)C10—N1—H1n117 (2)
C6—N1—C10122.2 (2)C1—C2—H2120.0
C2—C1—C5i121.3 (2)C3—C2—H2120.0
C2—C1—S1117.4 (2)C4—C3—H3119.7
C5i—C1—S1121.3 (2)C2—C3—H3119.7
C1—C2—C3120.0 (2)C3—C4—H4119.3
C4—C3—C2120.7 (2)C5—C4—H4119.3
C3—C4—C5121.3 (2)N1—C6—H6119.7
C4—C5—C5i118.8 (2)C7—C6—H6119.7
C4—C5—C1i123.3 (2)C6—C7—H7120.5
C5i—C5—C1i117.9 (2)C8—C7—H7120.5
N1—C6—C7120.7 (2)C10—C9—H9120.1
C6—C7—C8119.0 (2)C8—C9—H9120.1
C9—C8—C7118.3 (2)N1—C10—H10120.0
C9—C8—C8ii120.6 (2)C9—C10—H10120.0
O3—S1—C1—C23.8 (2)C3—C4—C5—C5i0.9 (2)
O1—S1—C1—C2117.0 (2)C3—C4—C5—C1i179.2 (2)
O2—S1—C1—C2123.7 (2)C10—N1—C6—C70.3 (4)
O3—S1—C1—C5i176.6 (2)N1—C6—C7—C80.1 (4)
O1—S1—C1—C5i62.7 (2)C6—C7—C8—C90.1 (3)
O2—S1—C1—C5i56.6 (2)C6—C7—C8—C8ii179.7 (2)
C5i—C1—C2—C30.9 (3)C7—C8—C9—C100.2 (3)
S1—C1—C2—C3178.7 (2)C8ii—C8—C9—C10179.6 (2)
C1—C2—C3—C40.4 (3)C6—N1—C10—C90.4 (4)
C2—C3—C4—C50.5 (3)C8—C9—C10—N10.3 (3)
Symmetry codes: (i) x+1, y, z+3/2; (ii) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O10.85 (1)2.00 (1)2.832 (3)167 (3)
O1w—H1w2···O2iii0.84 (1)1.99 (1)2.826 (2)176 (3)
N1—H1n···O1w0.86 (1)2.16 (2)2.810 (3)133 (2)
N1—H1n···O2iv0.86 (1)2.22 (2)2.885 (2)134 (2)
Symmetry codes: (iii) x, y1, z; (iv) x+1, y+1, z+1.
 

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