Download citation
Download citation
link to html
The asymmetric unit of the title compound [systematic name: 4,4'-bipyridinium bis­(2,3-dihydro-1,1,3-trioxo-1,2-benzothia­zol­ate) dihydrate], C10H10N2+·2C7H4NO3S-·2H2O, consists of one half of a 4,4'-bipyridinium cation, which has inversion symmetry, one saccharinate anion and one water mol­ecule. These ions and mol­ecules are further linked into a supra­molecular structure by inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030121/bx2014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030121/bx2014Isup2.hkl
Contains datablock I

CCDC reference: 620722

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.154
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.859(10) ...... 3.00 su-Ra N2 -H1' 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.857(19) ...... 2.11 su-Ra O4 -H42 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

4,4'-Bipyridinium bis(2,3-dihydro-1,1,3-trioxo-1,2-benzothiazolate) dihydrate top
Crystal data top
C10H10N22+·2C7H4NO3S·2H2OZ = 1
Mr = 558.58F(000) = 290
Triclinic, P1Dx = 1.504 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3215 (19) ÅCell parameters from 1530 reflections
b = 8.538 (2) Åθ = 2.6–21.8°
c = 9.629 (2) ŵ = 0.27 mm1
α = 94.368 (4)°T = 292 K
β = 102.874 (4)°Block, colourless
γ = 110.281 (4)°0.20 × 0.10 × 0.10 mm
V = 616.7 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2391 independent reflections
Radiation source: fine-focus sealed tube1777 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1010
Tmin = 0.947, Tmax = 0.973k = 1010
4792 measured reflectionsl = 1111
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0894P)2]
where P = (Fo2 + 2Fc2)/3
2391 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.44 e Å3
4 restraintsΔρmin = 0.39 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
S11.10076 (9)0.37789 (9)0.71539 (8)0.0502 (3)
N11.1423 (3)0.2945 (3)0.8583 (2)0.0483 (6)
N20.2553 (3)0.1403 (3)0.2310 (3)0.0475 (6)
C10.8720 (3)0.3300 (3)0.8591 (3)0.0360 (6)
C20.7252 (3)0.3256 (3)0.9045 (3)0.0462 (7)
H20.70800.28740.99000.055*
C30.6034 (4)0.3798 (4)0.8188 (3)0.0545 (7)
H30.50290.37790.84710.065*
C40.6301 (4)0.4364 (4)0.6925 (3)0.0566 (8)
H40.54640.47130.63650.068*
C50.7787 (4)0.4427 (3)0.6465 (3)0.0528 (7)
H50.79680.48110.56130.063*
C60.8982 (3)0.3891 (3)0.7340 (3)0.0403 (6)
C71.0190 (3)0.2751 (3)0.9298 (3)0.0392 (6)
C80.1999 (4)0.1048 (4)0.3469 (3)0.0550 (8)
H80.09540.11690.35530.066*
C90.2932 (4)0.0507 (4)0.4547 (3)0.0509 (7)
H90.25260.02670.53610.061*
C100.4488 (3)0.0312 (3)0.4430 (3)0.0363 (6)
C110.5043 (4)0.0734 (4)0.3219 (3)0.0552 (8)
H110.61000.06580.31150.066*
C120.4047 (4)0.1266 (4)0.2163 (3)0.0606 (8)
H120.44210.15310.13400.073*
O11.2317 (3)0.5436 (3)0.7286 (2)0.0675 (6)
O21.0732 (3)0.2632 (3)0.5878 (2)0.0717 (6)
O31.0186 (2)0.2134 (2)1.0429 (2)0.0517 (5)
O40.2537 (4)0.0068 (4)0.8514 (3)0.0817 (8)
H410.222 (5)0.091 (3)0.856 (5)0.113 (15)*
H420.185 (5)0.071 (4)0.886 (5)0.126 (18)*
H1'0.199 (4)0.175 (4)0.162 (2)0.068 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0521 (5)0.0606 (5)0.0490 (5)0.0252 (4)0.0254 (3)0.0190 (3)
N10.0435 (13)0.0619 (14)0.0524 (15)0.0282 (11)0.0202 (11)0.0216 (12)
N20.0451 (13)0.0521 (13)0.0447 (14)0.0217 (11)0.0035 (11)0.0127 (11)
C10.0360 (13)0.0384 (13)0.0350 (13)0.0159 (11)0.0080 (11)0.0094 (11)
C20.0410 (14)0.0538 (16)0.0476 (16)0.0193 (13)0.0149 (12)0.0138 (13)
C30.0391 (15)0.0568 (17)0.070 (2)0.0231 (13)0.0101 (14)0.0121 (15)
C40.0493 (17)0.0561 (17)0.0611 (19)0.0267 (14)0.0042 (14)0.0140 (15)
C50.0630 (19)0.0548 (17)0.0431 (16)0.0259 (15)0.0087 (14)0.0196 (13)
C60.0440 (14)0.0420 (14)0.0350 (14)0.0169 (12)0.0083 (11)0.0088 (11)
C70.0368 (13)0.0407 (14)0.0406 (15)0.0159 (11)0.0078 (11)0.0113 (12)
C80.0466 (16)0.081 (2)0.0506 (18)0.0387 (15)0.0123 (14)0.0189 (15)
C90.0425 (15)0.080 (2)0.0418 (16)0.0330 (14)0.0146 (12)0.0178 (14)
C100.0324 (12)0.0370 (13)0.0356 (13)0.0117 (10)0.0053 (10)0.0015 (11)
C110.0463 (16)0.085 (2)0.0491 (17)0.0353 (15)0.0192 (13)0.0269 (16)
C120.0588 (19)0.086 (2)0.0494 (18)0.0330 (17)0.0221 (15)0.0294 (16)
O10.0591 (13)0.0704 (14)0.0772 (16)0.0164 (11)0.0324 (11)0.0317 (12)
O20.0881 (16)0.0863 (15)0.0565 (13)0.0404 (13)0.0379 (12)0.0111 (11)
O30.0478 (11)0.0700 (13)0.0471 (12)0.0295 (10)0.0133 (9)0.0294 (10)
O40.0833 (18)0.0867 (18)0.117 (2)0.0539 (16)0.0624 (16)0.0456 (17)
Geometric parameters (Å, º) top
S1—O11.431 (2)C4—H40.9300
S1—O21.434 (2)C5—C61.382 (3)
S1—N11.621 (2)C5—H50.9300
S1—C61.768 (3)C7—O31.246 (3)
N1—C71.329 (3)C8—C91.362 (4)
N2—C81.317 (4)C8—H80.9300
N2—C121.325 (3)C9—C101.389 (3)
N2—H1'0.859 (10)C9—H90.9300
C1—C61.374 (3)C10—C111.375 (4)
C1—C21.375 (3)C10—C10i1.485 (5)
C1—C71.502 (3)C11—C121.372 (4)
C2—C31.391 (4)C11—H110.9300
C2—H20.9300C12—H120.9300
C3—C41.377 (4)O4—H410.853 (18)
C3—H30.9300O4—H420.857 (19)
C4—C51.389 (4)
O1—S1—O2114.85 (12)C4—C5—H5121.7
O1—S1—N1111.28 (13)C1—C6—C5122.3 (2)
O2—S1—N1110.40 (13)C1—C6—S1106.96 (18)
O1—S1—C6110.97 (12)C5—C6—S1130.7 (2)
O2—S1—C6111.31 (13)O3—C7—N1124.8 (2)
N1—S1—C696.58 (11)O3—C7—C1121.4 (2)
C7—N1—S1111.60 (17)N1—C7—C1113.8 (2)
C8—N2—C12121.1 (2)N2—C8—C9121.0 (3)
C8—N2—H1'122 (2)N2—C8—H8119.5
C12—N2—H1'117 (2)C9—C8—H8119.5
C6—C1—C2120.7 (2)C8—C9—C10120.0 (3)
C6—C1—C7111.0 (2)C8—C9—H9120.0
C2—C1—C7128.2 (2)C10—C9—H9120.0
C1—C2—C3118.0 (3)C11—C10—C9117.1 (2)
C1—C2—H2121.0C11—C10—C10i121.5 (3)
C3—C2—H2121.0C9—C10—C10i121.3 (3)
C4—C3—C2120.6 (3)C12—C11—C10120.4 (3)
C4—C3—H3119.7C12—C11—H11119.8
C2—C3—H3119.7C10—C11—H11119.8
C3—C4—C5121.8 (2)N2—C12—C11120.3 (3)
C3—C4—H4119.1N2—C12—H12119.9
C5—C4—H4119.1C11—C12—H12119.9
C6—C5—C4116.5 (3)H41—O4—H42107 (3)
C6—C5—H5121.7
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O3ii0.86 (2)1.81 (2)2.642 (3)163 (3)
O4—H41···N1iii0.86 (3)2.05 (3)2.913 (3)176 (4)
O4—H42···O3iv0.85 (3)2.00 (3)2.838 (3)168 (3)
C8—H8···O2iii0.932.563.154 (4)122
C11—H11···O4i0.932.293.095 (4)144
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z1; (iii) x1, y, z; (iv) x+1, y, z+2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds