4,4'-Bipyridinium disaccharinate dihydrate

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.

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

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Computing details

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

Crystal data

C10H10N2^2+·2C7H4NO3S^−·2H2O	Z = 1
Mr = 558.58	F(000) = 290
Triclinic, P1	Dx = 1.504 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3215 (19) Å	Cell parameters from 1530 reflections
b = 8.538 (2) Å	θ = 2.6–21.8°
c = 9.629 (2) Å	µ = 0.27 mm^−1
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) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2391 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.947, Tmax = 0.973	k = −10→10
4792 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0894P)^2] where P = (Fo^2 + 2Fc^2)/3
2391 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.44 e Å^−3
4 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.10076 (9)	0.37789 (9)	0.71539 (8)	0.0502 (3)
N1	1.1423 (3)	0.2945 (3)	0.8583 (2)	0.0483 (6)
N2	0.2553 (3)	0.1403 (3)	0.2310 (3)	0.0475 (6)
C1	0.8720 (3)	0.3300 (3)	0.8591 (3)	0.0360 (6)
C2	0.7252 (3)	0.3256 (3)	0.9045 (3)	0.0462 (7)
H2	0.7080	0.2874	0.9900	0.055*
C3	0.6034 (4)	0.3798 (4)	0.8188 (3)	0.0545 (7)
H3	0.5029	0.3779	0.8471	0.065*
C4	0.6301 (4)	0.4364 (4)	0.6925 (3)	0.0566 (8)
H4	0.5464	0.4713	0.6365	0.068*
C5	0.7787 (4)	0.4427 (3)	0.6465 (3)	0.0528 (7)
H5	0.7968	0.4811	0.5613	0.063*
C6	0.8982 (3)	0.3891 (3)	0.7340 (3)	0.0403 (6)
C7	1.0190 (3)	0.2751 (3)	0.9298 (3)	0.0392 (6)
C8	0.1999 (4)	0.1048 (4)	0.3469 (3)	0.0550 (8)
H8	0.0954	0.1169	0.3553	0.066*
C9	0.2932 (4)	0.0507 (4)	0.4547 (3)	0.0509 (7)
H9	0.2526	0.0267	0.5361	0.061*
C10	0.4488 (3)	0.0312 (3)	0.4430 (3)	0.0363 (6)
C11	0.5043 (4)	0.0734 (4)	0.3219 (3)	0.0552 (8)
H11	0.6100	0.0658	0.3115	0.066*
C12	0.4047 (4)	0.1266 (4)	0.2163 (3)	0.0606 (8)
H12	0.4421	0.1531	0.1340	0.073*
O1	1.2317 (3)	0.5436 (3)	0.7286 (2)	0.0675 (6)
O2	1.0732 (3)	0.2632 (3)	0.5878 (2)	0.0717 (6)
O3	1.0186 (2)	0.2134 (2)	1.0429 (2)	0.0517 (5)
O4	0.2537 (4)	0.0068 (4)	0.8514 (3)	0.0817 (8)
H41	0.222 (5)	0.091 (3)	0.856 (5)	0.113 (15)*
H42	0.185 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0521 (5)	0.0606 (5)	0.0490 (5)	0.0252 (4)	0.0254 (3)	0.0190 (3)
N1	0.0435 (13)	0.0619 (14)	0.0524 (15)	0.0282 (11)	0.0202 (11)	0.0216 (12)
N2	0.0451 (13)	0.0521 (13)	0.0447 (14)	0.0217 (11)	0.0035 (11)	0.0127 (11)
C1	0.0360 (13)	0.0384 (13)	0.0350 (13)	0.0159 (11)	0.0080 (11)	0.0094 (11)
C2	0.0410 (14)	0.0538 (16)	0.0476 (16)	0.0193 (13)	0.0149 (12)	0.0138 (13)
C3	0.0391 (15)	0.0568 (17)	0.070 (2)	0.0231 (13)	0.0101 (14)	0.0121 (15)
C4	0.0493 (17)	0.0561 (17)	0.0611 (19)	0.0267 (14)	−0.0042 (14)	0.0140 (15)
C5	0.0630 (19)	0.0548 (17)	0.0431 (16)	0.0259 (15)	0.0087 (14)	0.0196 (13)
C6	0.0440 (14)	0.0420 (14)	0.0350 (14)	0.0169 (12)	0.0083 (11)	0.0088 (11)
C7	0.0368 (13)	0.0407 (14)	0.0406 (15)	0.0159 (11)	0.0078 (11)	0.0113 (12)
C8	0.0466 (16)	0.081 (2)	0.0506 (18)	0.0387 (15)	0.0123 (14)	0.0189 (15)
C9	0.0425 (15)	0.080 (2)	0.0418 (16)	0.0330 (14)	0.0146 (12)	0.0178 (14)
C10	0.0324 (12)	0.0370 (13)	0.0356 (13)	0.0117 (10)	0.0053 (10)	0.0015 (11)
C11	0.0463 (16)	0.085 (2)	0.0491 (17)	0.0353 (15)	0.0192 (13)	0.0269 (16)
C12	0.0588 (19)	0.086 (2)	0.0494 (18)	0.0330 (17)	0.0221 (15)	0.0294 (16)
O1	0.0591 (13)	0.0704 (14)	0.0772 (16)	0.0164 (11)	0.0324 (11)	0.0317 (12)
O2	0.0881 (16)	0.0863 (15)	0.0565 (13)	0.0404 (13)	0.0379 (12)	0.0111 (11)
O3	0.0478 (11)	0.0700 (13)	0.0471 (12)	0.0295 (10)	0.0133 (9)	0.0294 (10)
O4	0.0833 (18)	0.0867 (18)	0.117 (2)	0.0539 (16)	0.0624 (16)	0.0456 (17)

Geometric parameters (Å, º)

S1—O1	1.431 (2)	C4—H4	0.9300
S1—O2	1.434 (2)	C5—C6	1.382 (3)
S1—N1	1.621 (2)	C5—H5	0.9300
S1—C6	1.768 (3)	C7—O3	1.246 (3)
N1—C7	1.329 (3)	C8—C9	1.362 (4)
N2—C8	1.317 (4)	C8—H8	0.9300
N2—C12	1.325 (3)	C9—C10	1.389 (3)
N2—H1'	0.859 (10)	C9—H9	0.9300
C1—C6	1.374 (3)	C10—C11	1.375 (4)
C1—C2	1.375 (3)	C10—C10^i	1.485 (5)
C1—C7	1.502 (3)	C11—C12	1.372 (4)
C2—C3	1.391 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.377 (4)	O4—H41	0.853 (18)
C3—H3	0.9300	O4—H42	0.857 (19)
C4—C5	1.389 (4)
O1—S1—O2	114.85 (12)	C4—C5—H5	121.7
O1—S1—N1	111.28 (13)	C1—C6—C5	122.3 (2)
O2—S1—N1	110.40 (13)	C1—C6—S1	106.96 (18)
O1—S1—C6	110.97 (12)	C5—C6—S1	130.7 (2)
O2—S1—C6	111.31 (13)	O3—C7—N1	124.8 (2)
N1—S1—C6	96.58 (11)	O3—C7—C1	121.4 (2)
C7—N1—S1	111.60 (17)	N1—C7—C1	113.8 (2)
C8—N2—C12	121.1 (2)	N2—C8—C9	121.0 (3)
C8—N2—H1'	122 (2)	N2—C8—H8	119.5
C12—N2—H1'	117 (2)	C9—C8—H8	119.5
C6—C1—C2	120.7 (2)	C8—C9—C10	120.0 (3)
C6—C1—C7	111.0 (2)	C8—C9—H9	120.0
C2—C1—C7	128.2 (2)	C10—C9—H9	120.0
C1—C2—C3	118.0 (3)	C11—C10—C9	117.1 (2)
C1—C2—H2	121.0	C11—C10—C10^i	121.5 (3)
C3—C2—H2	121.0	C9—C10—C10^i	121.3 (3)
C4—C3—C2	120.6 (3)	C12—C11—C10	120.4 (3)
C4—C3—H3	119.7	C12—C11—H11	119.8
C2—C3—H3	119.7	C10—C11—H11	119.8
C3—C4—C5	121.8 (2)	N2—C12—C11	120.3 (3)
C3—C4—H4	119.1	N2—C12—H12	119.9
C5—C4—H4	119.1	C11—C12—H12	119.9
C6—C5—C4	116.5 (3)	H41—O4—H42	107 (3)
C6—C5—H5	121.7

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1′···O3^ii	0.86 (2)	1.81 (2)	2.642 (3)	163 (3)
O4—H41···N1^iii	0.86 (3)	2.05 (3)	2.913 (3)	176 (4)
O4—H42···O3^iv	0.85 (3)	2.00 (3)	2.838 (3)	168 (3)
C8—H8···O2^iii	0.93	2.56	3.154 (4)	122
C11—H11···O4^i	0.93	2.29	3.095 (4)	144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z−1; (iii) x−1, y, z; (iv) −x+1, −y, −z+2.