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
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
No syntax errors found
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
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−·2H2O | Z = 1 |
Mr = 804.90 | F(000) = 418 |
Triclinic, P1 | Dx = 1.496 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.913 (2) Å | Cell parameters from 2035 reflections |
b = 11.192 (2) Å | θ = 2.0–25.0° |
c = 11.438 (3) Å | µ = 0.33 mm−1 |
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 tube | 2300 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.961, Tmax = 0.984 | k = −13→10 |
5746 measured reflections | l = −13→13 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-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 parameters | Δρmax = 0.33 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.51749 (14) | 0.19868 (10) | 0.26432 (10) | 0.0457 (3) | |
S2 | 0.62103 (14) | 0.00481 (10) | 0.28699 (11) | 0.0463 (3) | |
O1 | 0.1382 (4) | 0.5754 (3) | 0.1103 (3) | 0.0694 (10) | |
H1 | 0.0922 | 0.5964 | 0.1692 | 0.104* | |
O2 | 0.3007 (4) | 0.4177 (3) | 0.2676 (3) | 0.0616 (9) | |
O3 | 0.9871 (4) | −0.3504 (3) | 0.2877 (3) | 0.0580 (9) | |
O4 | 0.7378 (4) | −0.2463 (3) | 0.3422 (3) | 0.0557 (8) | |
C1 | 0.4429 (5) | 0.2827 (4) | 0.1024 (4) | 0.0397 (9) | |
C2 | 0.5041 (5) | 0.2291 (4) | 0.0112 (4) | 0.0456 (10) | |
H2 | 0.5850 | 0.1497 | 0.0342 | 0.055* | |
C3 | 0.4454 (6) | 0.2928 (5) | −0.1127 (4) | 0.0520 (11) | |
H3 | 0.4843 | 0.2547 | −0.1717 | 0.062* | |
C4 | 0.3306 (6) | 0.4115 (5) | −0.1491 (5) | 0.0585 (13) | |
H4 | 0.2931 | 0.4545 | −0.2332 | 0.070* | |
C5 | 0.2704 (6) | 0.4676 (4) | −0.0622 (4) | 0.0495 (11) | |
H5 | 0.1923 | 0.5485 | −0.0880 | 0.059* | |
C6 | 0.3249 (5) | 0.4048 (4) | 0.0646 (4) | 0.0386 (9) | |
C7 | 0.2546 (5) | 0.4657 (4) | 0.1571 (4) | 0.0437 (10) | |
C8 | 0.8397 (5) | 0.0074 (4) | 0.2184 (4) | 0.0366 (9) | |
C9 | 0.9021 (5) | 0.1276 (4) | 0.1585 (4) | 0.0431 (10) | |
H9 | 0.8314 | 0.2075 | 0.1543 | 0.052* | |
C10 | 1.0703 (5) | 0.1274 (4) | 0.1052 (4) | 0.0503 (11) | |
H10 | 1.1131 | 0.2073 | 0.0671 | 0.060* | |
C11 | 1.1737 (6) | 0.0112 (5) | 0.1081 (5) | 0.0528 (11) | |
H11 | 1.2857 | 0.0127 | 0.0712 | 0.063* | |
C12 | 1.1128 (5) | −0.1081 (4) | 0.1654 (4) | 0.0476 (10) | |
H12 | 1.1843 | −0.1868 | 0.1672 | 0.057* | |
C13 | 0.9447 (5) | −0.1121 (4) | 0.2209 (4) | 0.0364 (9) | |
C14 | 0.8865 (5) | −0.2458 (4) | 0.2869 (4) | 0.0409 (10) | |
N1 | 0.2185 (5) | 0.6895 (3) | 0.5036 (3) | 0.0488 (9) | |
H1A | 0.2715 | 0.6138 | 0.5033 | 0.059* | |
C15 | 0.2997 (7) | 0.7938 (5) | 0.4564 (5) | 0.0588 (12) | |
H15 | 0.4138 | 0.7843 | 0.4239 | 0.071* | |
C16 | 0.2166 (6) | 0.9155 (4) | 0.4554 (5) | 0.0519 (11) | |
H16 | 0.2759 | 0.9871 | 0.4225 | 0.062* | |
C17 | 0.0479 (5) | 0.9341 (4) | 0.5017 (4) | 0.0404 (9) | |
C18 | −0.0310 (6) | 0.8216 (4) | 0.5521 (4) | 0.0486 (11) | |
H18 | −0.1442 | 0.8282 | 0.5868 | 0.058* | |
C19 | 0.0550 (6) | 0.7015 (4) | 0.5516 (5) | 0.0498 (11) | |
H19 | −0.0006 | 0.6279 | 0.5848 | 0.060* | |
O1W | 0.3367 (4) | 0.4652 (3) | 0.4780 (3) | 0.0578 (8) | |
H1WA | 0.3027 | 0.4010 | 0.5415 | 0.087* | |
H1WB | 0.3037 | 0.4700 | 0.4094 | 0.087* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0507 (7) | 0.0354 (6) | 0.0443 (6) | 0.0085 (5) | −0.0012 (5) | −0.0180 (4) |
S2 | 0.0425 (6) | 0.0328 (5) | 0.0545 (7) | 0.0037 (4) | 0.0051 (5) | −0.0166 (5) |
O1 | 0.073 (2) | 0.053 (2) | 0.073 (2) | 0.0313 (17) | −0.0172 (19) | −0.0329 (17) |
O2 | 0.072 (2) | 0.0484 (18) | 0.059 (2) | 0.0147 (16) | −0.0054 (17) | −0.0274 (16) |
O3 | 0.058 (2) | 0.0372 (16) | 0.074 (2) | 0.0101 (14) | 0.0001 (17) | −0.0283 (15) |
O4 | 0.0499 (19) | 0.0358 (16) | 0.076 (2) | 0.0007 (14) | 0.0069 (16) | −0.0242 (15) |
C1 | 0.034 (2) | 0.037 (2) | 0.047 (2) | −0.0004 (17) | −0.0012 (18) | −0.0195 (17) |
C2 | 0.040 (2) | 0.046 (2) | 0.054 (3) | 0.0019 (19) | 0.000 (2) | −0.029 (2) |
C3 | 0.045 (2) | 0.066 (3) | 0.048 (3) | −0.007 (2) | 0.001 (2) | −0.029 (2) |
C4 | 0.056 (3) | 0.064 (3) | 0.051 (3) | −0.001 (2) | −0.012 (2) | −0.021 (2) |
C5 | 0.049 (3) | 0.039 (2) | 0.054 (3) | 0.0013 (19) | −0.011 (2) | −0.0153 (19) |
C6 | 0.033 (2) | 0.033 (2) | 0.051 (2) | −0.0046 (16) | 0.0008 (18) | −0.0199 (17) |
C7 | 0.042 (2) | 0.031 (2) | 0.057 (3) | −0.0005 (17) | −0.001 (2) | −0.0201 (19) |
C8 | 0.036 (2) | 0.0299 (19) | 0.039 (2) | 0.0025 (16) | −0.0049 (17) | −0.0129 (16) |
C9 | 0.041 (2) | 0.031 (2) | 0.051 (2) | −0.0008 (17) | −0.0042 (19) | −0.0132 (17) |
C10 | 0.045 (2) | 0.047 (2) | 0.058 (3) | −0.018 (2) | 0.003 (2) | −0.017 (2) |
C11 | 0.037 (2) | 0.057 (3) | 0.061 (3) | −0.011 (2) | 0.008 (2) | −0.023 (2) |
C12 | 0.037 (2) | 0.048 (2) | 0.059 (3) | 0.0024 (19) | 0.000 (2) | −0.029 (2) |
C13 | 0.032 (2) | 0.039 (2) | 0.038 (2) | 0.0013 (16) | −0.0049 (16) | −0.0184 (16) |
C14 | 0.043 (2) | 0.034 (2) | 0.046 (2) | 0.0061 (18) | −0.0078 (19) | −0.0204 (17) |
N1 | 0.056 (2) | 0.0290 (17) | 0.054 (2) | −0.0012 (16) | −0.0017 (18) | −0.0131 (15) |
C15 | 0.057 (3) | 0.046 (3) | 0.074 (3) | 0.003 (2) | −0.001 (2) | −0.031 (2) |
C16 | 0.053 (3) | 0.040 (2) | 0.062 (3) | −0.004 (2) | 0.000 (2) | −0.024 (2) |
C17 | 0.050 (2) | 0.036 (2) | 0.034 (2) | −0.0012 (18) | −0.0079 (18) | −0.0151 (16) |
C18 | 0.045 (2) | 0.032 (2) | 0.062 (3) | −0.0061 (18) | 0.005 (2) | −0.0143 (19) |
C19 | 0.045 (2) | 0.037 (2) | 0.064 (3) | −0.0088 (19) | −0.002 (2) | −0.016 (2) |
O1W | 0.067 (2) | 0.0409 (17) | 0.068 (2) | −0.0095 (15) | −0.0021 (17) | −0.0250 (15) |
Geometric parameters (Å, º) top
S1—C1 | 1.798 (4) | C9—H9 | 0.93 |
S1—S2 | 2.0602 (15) | C10—C11 | 1.366 (6) |
S2—C8 | 1.802 (4) | C10—H10 | 0.93 |
O1—C7 | 1.312 (5) | C11—C12 | 1.378 (6) |
O1—H1 | 0.82 | C11—H11 | 0.93 |
O2—C7 | 1.216 (5) | C12—C13 | 1.395 (6) |
O3—C14 | 1.260 (5) | C12—H12 | 0.93 |
O4—C14 | 1.259 (5) | C13—C14 | 1.506 (6) |
C1—C2 | 1.397 (6) | N1—C15 | 1.329 (6) |
C1—C6 | 1.404 (5) | N1—C19 | 1.337 (6) |
C2—C3 | 1.379 (6) | N1—H1A | 0.86 |
C2—H2 | 0.93 | C15—C16 | 1.372 (6) |
C3—C4 | 1.366 (6) | C15—H15 | 0.93 |
C3—H3 | 0.93 | C16—C17 | 1.374 (6) |
C4—C5 | 1.372 (7) | C16—H16 | 0.93 |
C4—H4 | 0.93 | C17—C18 | 1.392 (6) |
C5—C6 | 1.396 (6) | C17—C17i | 1.490 (8) |
C5—H5 | 0.93 | C18—C19 | 1.369 (6) |
C6—C7 | 1.478 (6) | C18—H18 | 0.93 |
C8—C9 | 1.392 (5) | C19—H19 | 0.93 |
C8—C13 | 1.402 (5) | O1W—H1WA | 0.84 |
C9—C10 | 1.387 (6) | O1W—H1WB | 0.84 |
| | | |
C1—S1—S2 | 105.11 (14) | C9—C10—H10 | 119.7 |
C8—S2—S1 | 106.17 (13) | C10—C11—C12 | 120.3 (4) |
C7—O1—H1 | 109.5 | C10—C11—H11 | 119.8 |
C2—C1—C6 | 118.8 (4) | C12—C11—H11 | 119.8 |
C2—C1—S1 | 120.6 (3) | C11—C12—C13 | 120.6 (4) |
C6—C1—S1 | 120.6 (3) | C11—C12—H12 | 119.7 |
C3—C2—C1 | 120.6 (4) | C13—C12—H12 | 119.7 |
C3—C2—H2 | 119.7 | C12—C13—C8 | 118.8 (4) |
C1—C2—H2 | 119.7 | C12—C13—C14 | 118.6 (4) |
C4—C3—C2 | 120.4 (4) | C8—C13—C14 | 122.6 (4) |
C4—C3—H3 | 119.8 | O4—C14—O3 | 123.3 (4) |
C2—C3—H3 | 119.8 | O4—C14—C13 | 116.7 (3) |
C3—C4—C5 | 120.3 (4) | O3—C14—C13 | 120.0 (4) |
C3—C4—H4 | 119.9 | C15—N1—C19 | 120.4 (4) |
C5—C4—H4 | 119.9 | C15—N1—H1A | 119.8 |
C4—C5—C6 | 120.8 (4) | C19—N1—H1A | 119.8 |
C4—C5—H5 | 119.6 | N1—C15—C16 | 120.5 (5) |
C6—C5—H5 | 119.6 | N1—C15—H15 | 119.8 |
C5—C6—C1 | 119.1 (4) | C16—C15—H15 | 119.8 |
C5—C6—C7 | 119.7 (4) | C15—C16—C17 | 121.6 (4) |
C1—C6—C7 | 121.2 (4) | C15—C16—H16 | 119.2 |
O2—C7—O1 | 122.9 (4) | C17—C16—H16 | 119.2 |
O2—C7—C6 | 122.7 (4) | C16—C17—C18 | 115.9 (4) |
O1—C7—C6 | 114.4 (4) | C16—C17—C17i | 123.0 (5) |
C9—C8—C13 | 120.0 (4) | C18—C17—C17i | 121.1 (5) |
C9—C8—S2 | 120.6 (3) | C19—C18—C17 | 121.2 (4) |
C13—C8—S2 | 119.4 (3) | C19—C18—H18 | 119.4 |
C10—C9—C8 | 119.6 (4) | C17—C18—H18 | 119.4 |
C10—C9—H9 | 120.2 | N1—C19—C18 | 120.4 (4) |
C8—C9—H9 | 120.2 | N1—C19—H19 | 119.8 |
C11—C10—C9 | 120.7 (4) | C18—C19—H19 | 119.8 |
C11—C10—H10 | 119.7 | H1WA—O1W—H1WB | 110.1 |
| | | |
C1—S1—S2—C8 | 83.48 (19) | C8—C9—C10—C11 | 1.6 (7) |
S2—S1—C1—C2 | −18.4 (4) | C9—C10—C11—C12 | −0.7 (7) |
S2—S1—C1—C6 | 162.9 (3) | C10—C11—C12—C13 | 0.2 (7) |
C6—C1—C2—C3 | −2.0 (6) | C11—C12—C13—C8 | −0.7 (6) |
S1—C1—C2—C3 | 179.3 (3) | C11—C12—C13—C14 | −177.7 (4) |
C1—C2—C3—C4 | 2.0 (7) | C9—C8—C13—C12 | 1.6 (6) |
C2—C3—C4—C5 | −1.0 (7) | S2—C8—C13—C12 | 178.9 (3) |
C3—C4—C5—C6 | 0.0 (7) | C9—C8—C13—C14 | 178.5 (4) |
C4—C5—C6—C1 | 0.0 (6) | S2—C8—C13—C14 | −4.2 (5) |
C4—C5—C6—C7 | −178.5 (4) | C12—C13—C14—O4 | 176.0 (4) |
C2—C1—C6—C5 | 1.0 (6) | C8—C13—C14—O4 | −0.9 (6) |
S1—C1—C6—C5 | 179.7 (3) | C12—C13—C14—O3 | −2.1 (6) |
C2—C1—C6—C7 | 179.5 (4) | C8—C13—C14—O3 | −179.1 (4) |
S1—C1—C6—C7 | −1.8 (5) | C19—N1—C15—C16 | −0.5 (7) |
C5—C6—C7—O2 | −177.9 (4) | N1—C15—C16—C17 | −0.4 (7) |
C1—C6—C7—O2 | 3.6 (6) | C15—C16—C17—C18 | 1.4 (7) |
C5—C6—C7—O1 | 2.3 (6) | C15—C16—C17—C17i | −178.1 (5) |
C1—C6—C7—O1 | −176.2 (4) | C16—C17—C18—C19 | −1.6 (6) |
S1—S2—C8—C9 | −3.3 (3) | C17i—C17—C18—C19 | 177.9 (5) |
S1—S2—C8—C13 | 179.3 (3) | C15—N1—C19—C18 | 0.3 (7) |
C13—C8—C9—C10 | −2.0 (6) | C17—C18—C19—N1 | 0.8 (7) |
S2—C8—C9—C10 | −179.3 (3) | | |
Symmetry code: (i) −x, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3ii | 0.82 | 1.75 | 2.566 (5) | 177 |
O1W—H1WA···O4iii | 0.84 | 1.74 | 2.569 (4) | 167 |
N1—H1A···O1W | 0.86 | 1.76 | 2.605 (5) | 165 |
O1W—H1WB···O2 | 0.84 | 1.95 | 2.738 (5) | 157 |
Symmetry codes: (ii) x−1, y+1, z; (iii) −x+1, −y, −z+1. |