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The title compound, C10H10N22+·2C14H9O4S2-·2H2O, was obtained by the reaction of Zn(NO3)2 with 2,2'-di­thio­di­benzoic acid and 4,4'-bi­pyridine in ethanol. The compound consists of hydrogen 2,2'-di­thio­dibenzoate anions, centrosymmetric 4,4'-bipyridyl­ium cations and water mol­ecules. Hydro­gen-bonding interactions between the components lead to the formation a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025565/ci6457sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025565/ci6457Isup2.hkl
Contains datablock I

CCDC reference: 255903

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.058
  • wR factor = 0.186
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C15 .. 5.08 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: XPREP in SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Hemi(4,4'-bipyridylium) hydrogen 2,2'-dithiodibenzoate monohydrate top
Crystal data top
C10H10N22+·2C14H9O4S2·2H2OZ = 1
Mr = 804.90F(000) = 418
Triclinic, P1Dx = 1.496 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.913 (2) ÅCell parameters from 2035 reflections
b = 11.192 (2) Åθ = 2.0–25.0°
c = 11.438 (3) ŵ = 0.33 mm1
α = 64.80 (2)°T = 293 K
β = 82.26 (3)°Prism, colourless
γ = 77.32 (3)°0.40 × 0.10 × 0.05 mm
V = 893.3 (4) Å3
Data collection top
Bruker P4
diffractometer
3140 independent reflections
Radiation source: fine-focus sealed tube2300 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.961, Tmax = 0.984k = 1310
5746 measured reflectionsl = 1313
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) = 0.186H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0812P)2 + 0.5264P]
where P = (Fo2 + 2Fc2)/3
3140 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.33 e Å3
3 restraintsΔρmin = 0.38 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.51749 (14)0.19868 (10)0.26432 (10)0.0457 (3)
S20.62103 (14)0.00481 (10)0.28699 (11)0.0463 (3)
O10.1382 (4)0.5754 (3)0.1103 (3)0.0694 (10)
H10.09220.59640.16920.104*
O20.3007 (4)0.4177 (3)0.2676 (3)0.0616 (9)
O30.9871 (4)0.3504 (3)0.2877 (3)0.0580 (9)
O40.7378 (4)0.2463 (3)0.3422 (3)0.0557 (8)
C10.4429 (5)0.2827 (4)0.1024 (4)0.0397 (9)
C20.5041 (5)0.2291 (4)0.0112 (4)0.0456 (10)
H20.58500.14970.03420.055*
C30.4454 (6)0.2928 (5)0.1127 (4)0.0520 (11)
H30.48430.25470.17170.062*
C40.3306 (6)0.4115 (5)0.1491 (5)0.0585 (13)
H40.29310.45450.23320.070*
C50.2704 (6)0.4676 (4)0.0622 (4)0.0495 (11)
H50.19230.54850.08800.059*
C60.3249 (5)0.4048 (4)0.0646 (4)0.0386 (9)
C70.2546 (5)0.4657 (4)0.1571 (4)0.0437 (10)
C80.8397 (5)0.0074 (4)0.2184 (4)0.0366 (9)
C90.9021 (5)0.1276 (4)0.1585 (4)0.0431 (10)
H90.83140.20750.15430.052*
C101.0703 (5)0.1274 (4)0.1052 (4)0.0503 (11)
H101.11310.20730.06710.060*
C111.1737 (6)0.0112 (5)0.1081 (5)0.0528 (11)
H111.28570.01270.07120.063*
C121.1128 (5)0.1081 (4)0.1654 (4)0.0476 (10)
H121.18430.18680.16720.057*
C130.9447 (5)0.1121 (4)0.2209 (4)0.0364 (9)
C140.8865 (5)0.2458 (4)0.2869 (4)0.0409 (10)
N10.2185 (5)0.6895 (3)0.5036 (3)0.0488 (9)
H1A0.27150.61380.50330.059*
C150.2997 (7)0.7938 (5)0.4564 (5)0.0588 (12)
H150.41380.78430.42390.071*
C160.2166 (6)0.9155 (4)0.4554 (5)0.0519 (11)
H160.27590.98710.42250.062*
C170.0479 (5)0.9341 (4)0.5017 (4)0.0404 (9)
C180.0310 (6)0.8216 (4)0.5521 (4)0.0486 (11)
H180.14420.82820.58680.058*
C190.0550 (6)0.7015 (4)0.5516 (5)0.0498 (11)
H190.00060.62790.58480.060*
O1W0.3367 (4)0.4652 (3)0.4780 (3)0.0578 (8)
H1WA0.30270.40100.54150.087*
H1WB0.30370.47000.40940.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0507 (7)0.0354 (6)0.0443 (6)0.0085 (5)0.0012 (5)0.0180 (4)
S20.0425 (6)0.0328 (5)0.0545 (7)0.0037 (4)0.0051 (5)0.0166 (5)
O10.073 (2)0.053 (2)0.073 (2)0.0313 (17)0.0172 (19)0.0329 (17)
O20.072 (2)0.0484 (18)0.059 (2)0.0147 (16)0.0054 (17)0.0274 (16)
O30.058 (2)0.0372 (16)0.074 (2)0.0101 (14)0.0001 (17)0.0283 (15)
O40.0499 (19)0.0358 (16)0.076 (2)0.0007 (14)0.0069 (16)0.0242 (15)
C10.034 (2)0.037 (2)0.047 (2)0.0004 (17)0.0012 (18)0.0195 (17)
C20.040 (2)0.046 (2)0.054 (3)0.0019 (19)0.000 (2)0.029 (2)
C30.045 (2)0.066 (3)0.048 (3)0.007 (2)0.001 (2)0.029 (2)
C40.056 (3)0.064 (3)0.051 (3)0.001 (2)0.012 (2)0.021 (2)
C50.049 (3)0.039 (2)0.054 (3)0.0013 (19)0.011 (2)0.0153 (19)
C60.033 (2)0.033 (2)0.051 (2)0.0046 (16)0.0008 (18)0.0199 (17)
C70.042 (2)0.031 (2)0.057 (3)0.0005 (17)0.001 (2)0.0201 (19)
C80.036 (2)0.0299 (19)0.039 (2)0.0025 (16)0.0049 (17)0.0129 (16)
C90.041 (2)0.031 (2)0.051 (2)0.0008 (17)0.0042 (19)0.0132 (17)
C100.045 (2)0.047 (2)0.058 (3)0.018 (2)0.003 (2)0.017 (2)
C110.037 (2)0.057 (3)0.061 (3)0.011 (2)0.008 (2)0.023 (2)
C120.037 (2)0.048 (2)0.059 (3)0.0024 (19)0.000 (2)0.029 (2)
C130.032 (2)0.039 (2)0.038 (2)0.0013 (16)0.0049 (16)0.0184 (16)
C140.043 (2)0.034 (2)0.046 (2)0.0061 (18)0.0078 (19)0.0204 (17)
N10.056 (2)0.0290 (17)0.054 (2)0.0012 (16)0.0017 (18)0.0131 (15)
C150.057 (3)0.046 (3)0.074 (3)0.003 (2)0.001 (2)0.031 (2)
C160.053 (3)0.040 (2)0.062 (3)0.004 (2)0.000 (2)0.024 (2)
C170.050 (2)0.036 (2)0.034 (2)0.0012 (18)0.0079 (18)0.0151 (16)
C180.045 (2)0.032 (2)0.062 (3)0.0061 (18)0.005 (2)0.0143 (19)
C190.045 (2)0.037 (2)0.064 (3)0.0088 (19)0.002 (2)0.016 (2)
O1W0.067 (2)0.0409 (17)0.068 (2)0.0095 (15)0.0021 (17)0.0250 (15)
Geometric parameters (Å, º) top
S1—C11.798 (4)C9—H90.93
S1—S22.0602 (15)C10—C111.366 (6)
S2—C81.802 (4)C10—H100.93
O1—C71.312 (5)C11—C121.378 (6)
O1—H10.82C11—H110.93
O2—C71.216 (5)C12—C131.395 (6)
O3—C141.260 (5)C12—H120.93
O4—C141.259 (5)C13—C141.506 (6)
C1—C21.397 (6)N1—C151.329 (6)
C1—C61.404 (5)N1—C191.337 (6)
C2—C31.379 (6)N1—H1A0.86
C2—H20.93C15—C161.372 (6)
C3—C41.366 (6)C15—H150.93
C3—H30.93C16—C171.374 (6)
C4—C51.372 (7)C16—H160.93
C4—H40.93C17—C181.392 (6)
C5—C61.396 (6)C17—C17i1.490 (8)
C5—H50.93C18—C191.369 (6)
C6—C71.478 (6)C18—H180.93
C8—C91.392 (5)C19—H190.93
C8—C131.402 (5)O1W—H1WA0.84
C9—C101.387 (6)O1W—H1WB0.84
C1—S1—S2105.11 (14)C9—C10—H10119.7
C8—S2—S1106.17 (13)C10—C11—C12120.3 (4)
C7—O1—H1109.5C10—C11—H11119.8
C2—C1—C6118.8 (4)C12—C11—H11119.8
C2—C1—S1120.6 (3)C11—C12—C13120.6 (4)
C6—C1—S1120.6 (3)C11—C12—H12119.7
C3—C2—C1120.6 (4)C13—C12—H12119.7
C3—C2—H2119.7C12—C13—C8118.8 (4)
C1—C2—H2119.7C12—C13—C14118.6 (4)
C4—C3—C2120.4 (4)C8—C13—C14122.6 (4)
C4—C3—H3119.8O4—C14—O3123.3 (4)
C2—C3—H3119.8O4—C14—C13116.7 (3)
C3—C4—C5120.3 (4)O3—C14—C13120.0 (4)
C3—C4—H4119.9C15—N1—C19120.4 (4)
C5—C4—H4119.9C15—N1—H1A119.8
C4—C5—C6120.8 (4)C19—N1—H1A119.8
C4—C5—H5119.6N1—C15—C16120.5 (5)
C6—C5—H5119.6N1—C15—H15119.8
C5—C6—C1119.1 (4)C16—C15—H15119.8
C5—C6—C7119.7 (4)C15—C16—C17121.6 (4)
C1—C6—C7121.2 (4)C15—C16—H16119.2
O2—C7—O1122.9 (4)C17—C16—H16119.2
O2—C7—C6122.7 (4)C16—C17—C18115.9 (4)
O1—C7—C6114.4 (4)C16—C17—C17i123.0 (5)
C9—C8—C13120.0 (4)C18—C17—C17i121.1 (5)
C9—C8—S2120.6 (3)C19—C18—C17121.2 (4)
C13—C8—S2119.4 (3)C19—C18—H18119.4
C10—C9—C8119.6 (4)C17—C18—H18119.4
C10—C9—H9120.2N1—C19—C18120.4 (4)
C8—C9—H9120.2N1—C19—H19119.8
C11—C10—C9120.7 (4)C18—C19—H19119.8
C11—C10—H10119.7H1WA—O1W—H1WB110.1
C1—S1—S2—C883.48 (19)C8—C9—C10—C111.6 (7)
S2—S1—C1—C218.4 (4)C9—C10—C11—C120.7 (7)
S2—S1—C1—C6162.9 (3)C10—C11—C12—C130.2 (7)
C6—C1—C2—C32.0 (6)C11—C12—C13—C80.7 (6)
S1—C1—C2—C3179.3 (3)C11—C12—C13—C14177.7 (4)
C1—C2—C3—C42.0 (7)C9—C8—C13—C121.6 (6)
C2—C3—C4—C51.0 (7)S2—C8—C13—C12178.9 (3)
C3—C4—C5—C60.0 (7)C9—C8—C13—C14178.5 (4)
C4—C5—C6—C10.0 (6)S2—C8—C13—C144.2 (5)
C4—C5—C6—C7178.5 (4)C12—C13—C14—O4176.0 (4)
C2—C1—C6—C51.0 (6)C8—C13—C14—O40.9 (6)
S1—C1—C6—C5179.7 (3)C12—C13—C14—O32.1 (6)
C2—C1—C6—C7179.5 (4)C8—C13—C14—O3179.1 (4)
S1—C1—C6—C71.8 (5)C19—N1—C15—C160.5 (7)
C5—C6—C7—O2177.9 (4)N1—C15—C16—C170.4 (7)
C1—C6—C7—O23.6 (6)C15—C16—C17—C181.4 (7)
C5—C6—C7—O12.3 (6)C15—C16—C17—C17i178.1 (5)
C1—C6—C7—O1176.2 (4)C16—C17—C18—C191.6 (6)
S1—S2—C8—C93.3 (3)C17i—C17—C18—C19177.9 (5)
S1—S2—C8—C13179.3 (3)C15—N1—C19—C180.3 (7)
C13—C8—C9—C102.0 (6)C17—C18—C19—N10.8 (7)
S2—C8—C9—C10179.3 (3)
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3ii0.821.752.566 (5)177
O1W—H1WA···O4iii0.841.742.569 (4)167
N1—H1A···O1W0.861.762.605 (5)165
O1W—H1WB···O20.841.952.738 (5)157
Symmetry codes: (ii) x1, y+1, z; (iii) x+1, y, z+1.
 

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