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
CCDC reference: 236111
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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·C10H6O6S2·2H2O | F(000) = 500 |
Mr = 480.50 | Dx = 1.572 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 1542 reflections |
a = 9.8121 (9) Å | θ = 2.7–27.1° |
b = 6.6775 (6) Å | µ = 0.32 mm−1 |
c = 15.647 (1) Å | T = 298 K |
β = 97.957 (2)° | Plate, colorless |
V = 1015.3 (2) Å3 | 0.27 × 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 tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
φ and ω scan | h = −12→5 |
5865 measured reflections | k = −8→8 |
2296 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H 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 parameters | Δρmax = 0.23 e Å−3 |
3 restraints | Δρmin = −0.40 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.75151 (5) | 0.63522 (8) | 0.61589 (3) | 0.0323 (2) | |
O1 | 0.7097 (2) | 0.4480 (3) | 0.5733 (1) | 0.0457 (4) | |
O2 | 0.6972 (2) | 0.8078 (3) | 0.5656 (1) | 0.0493 (5) | |
O3 | 0.8980 (2) | 0.6489 (3) | 0.6413 (1) | 0.0505 (5) | |
O1w | 0.5272 (2) | 0.1319 (3) | 0.5991 (1) | 0.0510 (5) | |
N1 | 0.2441 (2) | 0.1582 (3) | 0.6095 (1) | 0.0434 (5) | |
C1 | 0.6736 (2) | 0.6384 (3) | 0.7126 (1) | 0.0282 (4) | |
C2 | 0.7594 (2) | 0.6403 (3) | 0.7893 (1) | 0.0316 (5) | |
C3 | 0.7042 (2) | 0.6389 (3) | 0.8677 (1) | 0.0326 (5) | |
C4 | 0.5662 (2) | 0.6370 (3) | 0.8682 (1) | 0.0308 (5) | |
C5 | 0.4729 (2) | 0.6378 (3) | 0.7901 (1) | 0.0268 (4) | |
C6 | 0.1137 (3) | 0.1892 (4) | 0.5782 (2) | 0.0479 (6) | |
C7 | 0.0137 (2) | 0.1895 (4) | 0.6318 (1) | 0.0431 (6) | |
C8 | 0.0519 (2) | 0.1569 (3) | 0.7199 (1) | 0.0305 (5) | |
C9 | 0.1893 (2) | 0.1253 (3) | 0.7497 (2) | 0.0395 (5) | |
C10 | 0.2847 (3) | 0.1271 (3) | 0.6927 (2) | 0.0463 (6) | |
H1w1 | 0.571 (3) | 0.238 (3) | 0.591 (2) | 0.08 (1)* | |
H1w2 | 0.574 (3) | 0.033 (3) | 0.587 (2) | 0.08 (1)* | |
H1n | 0.306 (2) | 0.154 (3) | 0.576 (2) | 0.05 (1)* | |
H2 | 0.8543 | 0.6426 | 0.7897 | 0.038* | |
H3 | 0.7631 | 0.6393 | 0.9197 | 0.039* | |
H4 | 0.5318 | 0.6351 | 0.9207 | 0.037* | |
H6 | 0.0893 | 0.2110 | 0.5194 | 0.057* | |
H7 | −0.0780 | 0.2111 | 0.6096 | 0.052* | |
H9 | 0.2175 | 0.1028 | 0.8082 | 0.047* | |
H10 | 0.3774 | 0.1065 | 0.7127 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0307 (3) | 0.0440 (3) | 0.0249 (3) | 0.0036 (2) | 0.0132 (2) | 0.0018 (2) |
O1 | 0.052 (1) | 0.054 (1) | 0.036 (1) | −0.002 (1) | 0.019 (1) | −0.011 (1) |
O2 | 0.057 (1) | 0.057 (1) | 0.040 (1) | 0.017 (1) | 0.029 (1) | 0.018 (1) |
O3 | 0.030 (1) | 0.083 (1) | 0.042 (1) | 0.000 (1) | 0.015 (1) | −0.002 (1) |
O1w | 0.037 (1) | 0.054 (1) | 0.066 (1) | 0.004 (1) | 0.018 (1) | 0.000 (1) |
N1 | 0.047 (1) | 0.042 (1) | 0.049 (1) | −0.001 (1) | 0.032 (1) | −0.002 (1) |
C1 | 0.030 (1) | 0.032 (1) | 0.025 (1) | 0.001 (1) | 0.011 (1) | 0.001 (1) |
C2 | 0.028 (1) | 0.038 (1) | 0.030 (1) | −0.001 (1) | 0.005 (1) | 0.002 (1) |
C3 | 0.034 (1) | 0.040 (1) | 0.023 (1) | −0.001 (1) | 0.002 (1) | 0.002 (1) |
C4 | 0.033 (1) | 0.041 (1) | 0.020 (1) | −0.001 (1) | 0.008 (1) | 0.001 (1) |
C5 | 0.030 (1) | 0.031 (1) | 0.022 (1) | −0.000 (1) | 0.009 (1) | 0.000 (1) |
C6 | 0.053 (2) | 0.062 (2) | 0.032 (1) | −0.001 (1) | 0.018 (1) | 0.004 (1) |
C7 | 0.037 (1) | 0.062 (2) | 0.032 (1) | 0.002 (1) | 0.012 (1) | 0.005 (1) |
C8 | 0.032 (1) | 0.032 (1) | 0.030 (1) | −0.001 (1) | 0.013 (1) | −0.002 (1) |
C9 | 0.035 (1) | 0.047 (1) | 0.039 (1) | 0.003 (1) | 0.011 (1) | 0.002 (1) |
C10 | 0.033 (1) | 0.052 (2) | 0.057 (2) | 0.003 (1) | 0.017 (1) | 0.000 (1) |
Geometric parameters (Å, º) top
S1—O1 | 1.449 (2) | C8—C9 | 1.381 (3) |
S1—O2 | 1.454 (2) | C8—C8ii | 1.480 (4) |
S1—O3 | 1.440 (2) | C9—C10 | 1.380 (3) |
S1—C1 | 1.787 (2) | O1w—H1w1 | 0.85 (1) |
N1—C6 | 1.321 (3) | O1w—H1w2 | 0.84 (1) |
N1—C10 | 1.325 (3) | N1—H1n | 0.86 (1) |
C1—C2 | 1.367 (3) | C2—H2 | 0.93 |
C1—C5i | 1.433 (3) | C3—H3 | 0.93 |
C2—C3 | 1.408 (3) | C4—H4 | 0.93 |
C3—C4 | 1.356 (3) | C6—H6 | 0.93 |
C4—C5 | 1.422 (3) | C7—H7 | 0.93 |
C5—C5i | 1.430 (4) | C9—H9 | 0.93 |
C6—C7 | 1.376 (3) | C10—H10 | 0.93 |
C7—C8 | 1.394 (3) | | |
| | | |
O1—S1—O2 | 112.1 (1) | C7—C8—C8ii | 121.0 (3) |
O1—S1—O3 | 113.0 (1) | C10—C9—C8 | 119.9 (2) |
O2—S1—O3 | 112.1 (1) | N1—C10—C9 | 119.9 (2) |
O1—S1—C1 | 105.8 (1) | H1w1—O1w—H1w2 | 109 (3) |
O2—S1—C1 | 106.3 (1) | C6—N1—H1n | 120 (2) |
O3—S1—C1 | 107.0 (1) | C10—N1—H1n | 117 (2) |
C6—N1—C10 | 122.2 (2) | C1—C2—H2 | 120.0 |
C2—C1—C5i | 121.3 (2) | C3—C2—H2 | 120.0 |
C2—C1—S1 | 117.4 (2) | C4—C3—H3 | 119.7 |
C5i—C1—S1 | 121.3 (2) | C2—C3—H3 | 119.7 |
C1—C2—C3 | 120.0 (2) | C3—C4—H4 | 119.3 |
C4—C3—C2 | 120.7 (2) | C5—C4—H4 | 119.3 |
C3—C4—C5 | 121.3 (2) | N1—C6—H6 | 119.7 |
C4—C5—C5i | 118.8 (2) | C7—C6—H6 | 119.7 |
C4—C5—C1i | 123.3 (2) | C6—C7—H7 | 120.5 |
C5i—C5—C1i | 117.9 (2) | C8—C7—H7 | 120.5 |
N1—C6—C7 | 120.7 (2) | C10—C9—H9 | 120.1 |
C6—C7—C8 | 119.0 (2) | C8—C9—H9 | 120.1 |
C9—C8—C7 | 118.3 (2) | N1—C10—H10 | 120.0 |
C9—C8—C8ii | 120.6 (2) | C9—C10—H10 | 120.0 |
| | | |
O3—S1—C1—C2 | −3.8 (2) | C3—C4—C5—C5i | 0.9 (2) |
O1—S1—C1—C2 | 117.0 (2) | C3—C4—C5—C1i | −179.2 (2) |
O2—S1—C1—C2 | −123.7 (2) | C10—N1—C6—C7 | −0.3 (4) |
O3—S1—C1—C5i | 176.6 (2) | N1—C6—C7—C8 | 0.1 (4) |
O1—S1—C1—C5i | −62.7 (2) | C6—C7—C8—C9 | −0.1 (3) |
O2—S1—C1—C5i | 56.6 (2) | C6—C7—C8—C8ii | 179.7 (2) |
C5i—C1—C2—C3 | 0.9 (3) | C7—C8—C9—C10 | 0.2 (3) |
S1—C1—C2—C3 | −178.7 (2) | C8ii—C8—C9—C10 | −179.6 (2) |
C1—C2—C3—C4 | −0.4 (3) | C6—N1—C10—C9 | 0.4 (4) |
C2—C3—C4—C5 | −0.5 (3) | C8—C9—C10—N1 | −0.3 (3) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1 | 0.85 (1) | 2.00 (1) | 2.832 (3) | 167 (3) |
O1w—H1w2···O2iii | 0.84 (1) | 1.99 (1) | 2.826 (2) | 176 (3) |
N1—H1n···O1w | 0.86 (1) | 2.16 (2) | 2.810 (3) | 133 (2) |
N1—H1n···O2iv | 0.86 (1) | 2.22 (2) | 2.885 (2) | 134 (2) |
Symmetry codes: (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |