The chemical structural unit of the title compound [systematic name: bis(4,4′-bipyridin-1-ium) bis(5-fluoro-1,2,3,6-tetrahydro-2,6-dioxopyrimidine-3-acetate) monohydrate], 2C
10H
9N
2+·2C
6H
4FN
2O
4−·H
2O, comprises two ion pairs and one water molecule, which lies on a twofold rotation axis. O—H
O, N—H
O and N—H
N hydrogen-bond interactions connect the cations, anions and water molecules to produce a ribbon-like double-chain along the [101] direction. The hydrogen-bonding pattern can be described in graph-set notation as
R68(24)C
22(16).
Supporting information
CCDC reference: 285499
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.076
- wR factor = 0.189
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT731_ALERT_1_C Bond Calc 0.90(5), Rep 0.900(19) ...... 2.63 su-Rat
O5 -H5 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.90(5), Rep 0.900(19) ...... 2.63 su-Rat
O5 -H5 1.555 1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C6 H4 F N2 O4
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
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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 (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
bis(4,4'-bipyridin-1-ium)
bis(5-fluoro-1,2,3,6-tetrahydro-2,6-dioxopyrimidine-3-acetate) monohydrate
top
Crystal data top
2C10H9N2+·2C6H4FN2O4−·H2O | F(000) = 732 |
Mr = 706.62 | Dx = 1.486 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 1246 reflections |
a = 14.2530 (15) Å | θ = 2.8–24.1° |
b = 4.9385 (5) Å | µ = 0.12 mm−1 |
c = 25.868 (2) Å | T = 298 K |
β = 119.826 (2)° | Block, colorless |
V = 1579.6 (3) Å3 | 0.28 × 0.22 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker APEX area-detector diffractometer | 2783 independent reflections |
Radiation source: fine-focus sealed tube | 2156 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→16 |
Tmin = 0.971, Tmax = 0.990 | k = −5→5 |
7788 measured reflections | l = −30→27 |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0742P)2 + 0.8989P] where P = (Fo2 + 2Fc2)/3 |
2783 reflections | (Δ/σ)max = 0.001 |
240 parameters | Δρmax = 0.21 e Å−3 |
3 restraints | Δρmin = −0.34 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 | |
F1 | 1.1668 (2) | 1.1647 (7) | 0.86189 (13) | 0.1121 (11) | |
O1 | 1.02399 (19) | 0.9817 (5) | 0.57816 (10) | 0.0619 (7) | |
O2 | 1.0314 (2) | 0.7582 (6) | 0.65441 (10) | 0.0676 (8) | |
O3 | 1.3027 (2) | 0.7272 (5) | 0.72275 (10) | 0.0617 (7) | |
O4 | 1.3211 (2) | 0.7590 (7) | 0.90292 (11) | 0.0856 (10) | |
O5 | 1.0000 | 0.6086 (10) | 0.7500 | 0.0943 (14) | |
H5 | 1.007 (4) | 0.693 (10) | 0.7211 (18) | 0.113* | |
N1 | 1.2025 (2) | 1.0475 (5) | 0.73641 (11) | 0.0472 (7) | |
N2 | 1.3099 (2) | 0.7497 (6) | 0.81224 (11) | 0.0476 (7) | |
H2 | 1.360 (2) | 0.624 (6) | 0.8249 (15) | 0.057* | |
N3 | 0.8762 (2) | 0.6378 (6) | 0.51470 (12) | 0.0497 (7) | |
H3 | 0.930 (2) | 0.759 (6) | 0.5363 (14) | 0.060* | |
N4 | 0.4660 (2) | −0.3294 (6) | 0.35936 (13) | 0.0578 (8) | |
C1 | 1.0615 (3) | 0.9348 (7) | 0.63367 (14) | 0.0468 (8) | |
C2 | 1.1516 (3) | 1.1261 (7) | 0.67402 (14) | 0.0549 (9) | |
H2A | 1.2059 | 1.1300 | 0.6618 | 0.066* | |
H2B | 1.1224 | 1.3075 | 0.6695 | 0.066* | |
C3 | 1.2733 (3) | 0.8338 (7) | 0.75482 (14) | 0.0436 (8) | |
C4 | 1.2815 (3) | 0.8489 (8) | 0.85202 (15) | 0.0577 (10) | |
C5 | 1.2032 (3) | 1.0608 (9) | 0.82737 (17) | 0.0640 (11) | |
C6 | 1.1667 (3) | 1.1534 (8) | 0.77263 (17) | 0.0597 (10) | |
H6 | 1.1159 | 1.2924 | 0.7584 | 0.072* | |
C7 | 0.8497 (3) | 0.5690 (8) | 0.45959 (14) | 0.0577 (10) | |
H7 | 0.8865 | 0.6481 | 0.4422 | 0.069* | |
C8 | 0.7699 (3) | 0.3848 (8) | 0.42755 (14) | 0.0531 (9) | |
H8 | 0.7529 | 0.3418 | 0.3889 | 0.064* | |
C9 | 0.7144 (3) | 0.2625 (7) | 0.45223 (13) | 0.0436 (8) | |
C10 | 0.7442 (3) | 0.3395 (8) | 0.50993 (15) | 0.0628 (11) | |
H10 | 0.7089 | 0.2647 | 0.5286 | 0.075* | |
C11 | 0.8252 (3) | 0.5247 (9) | 0.53976 (15) | 0.0647 (11) | |
H11 | 0.8446 | 0.5715 | 0.5786 | 0.078* | |
C12 | 0.6277 (2) | 0.0606 (7) | 0.41997 (13) | 0.0430 (8) | |
C13 | 0.5865 (3) | 0.0045 (8) | 0.35975 (14) | 0.0585 (10) | |
H13 | 0.6124 | 0.0981 | 0.3382 | 0.070* | |
C14 | 0.5079 (3) | −0.1885 (8) | 0.33219 (16) | 0.0635 (11) | |
H14 | 0.4824 | −0.2224 | 0.2920 | 0.076* | |
C15 | 0.5836 (3) | −0.0865 (7) | 0.44798 (15) | 0.0554 (9) | |
H15 | 0.6076 | −0.0577 | 0.4882 | 0.067* | |
C16 | 0.5045 (3) | −0.2754 (8) | 0.41682 (16) | 0.0597 (10) | |
H16 | 0.4762 | −0.3707 | 0.4370 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.122 (2) | 0.144 (3) | 0.098 (2) | 0.0009 (19) | 0.0752 (18) | −0.0487 (19) |
O1 | 0.0714 (17) | 0.0646 (16) | 0.0401 (13) | −0.0148 (13) | 0.0205 (12) | 0.0061 (12) |
O2 | 0.0760 (18) | 0.0694 (17) | 0.0502 (14) | −0.0263 (14) | 0.0257 (13) | 0.0019 (13) |
O3 | 0.0753 (17) | 0.0690 (17) | 0.0489 (14) | 0.0129 (13) | 0.0371 (13) | 0.0023 (12) |
O4 | 0.092 (2) | 0.124 (3) | 0.0425 (15) | −0.0170 (18) | 0.0343 (14) | 0.0016 (16) |
O5 | 0.126 (4) | 0.074 (3) | 0.110 (4) | 0.000 | 0.078 (3) | 0.000 |
N1 | 0.0544 (17) | 0.0379 (15) | 0.0417 (15) | −0.0002 (13) | 0.0181 (13) | −0.0042 (12) |
N2 | 0.0517 (17) | 0.0507 (17) | 0.0374 (15) | 0.0003 (13) | 0.0200 (13) | 0.0019 (13) |
N3 | 0.0499 (17) | 0.0509 (17) | 0.0423 (16) | −0.0056 (14) | 0.0183 (13) | 0.0019 (13) |
N4 | 0.0530 (18) | 0.0612 (19) | 0.0499 (18) | 0.0004 (15) | 0.0186 (15) | −0.0085 (15) |
C1 | 0.051 (2) | 0.0407 (18) | 0.0462 (19) | 0.0006 (16) | 0.0227 (16) | 0.0044 (15) |
C2 | 0.061 (2) | 0.0405 (19) | 0.0473 (19) | −0.0005 (17) | 0.0149 (17) | 0.0083 (16) |
C3 | 0.0463 (19) | 0.0427 (19) | 0.0392 (17) | −0.0043 (15) | 0.0194 (15) | −0.0029 (14) |
C4 | 0.057 (2) | 0.076 (3) | 0.042 (2) | −0.020 (2) | 0.0248 (17) | −0.0117 (19) |
C5 | 0.063 (2) | 0.078 (3) | 0.057 (2) | −0.012 (2) | 0.035 (2) | −0.031 (2) |
C6 | 0.052 (2) | 0.048 (2) | 0.067 (3) | 0.0000 (17) | 0.0213 (19) | −0.0178 (19) |
C7 | 0.067 (2) | 0.067 (2) | 0.044 (2) | −0.009 (2) | 0.0313 (18) | 0.0034 (18) |
C8 | 0.065 (2) | 0.062 (2) | 0.0349 (17) | −0.0072 (19) | 0.0273 (16) | −0.0030 (16) |
C9 | 0.0430 (18) | 0.0490 (19) | 0.0347 (16) | 0.0092 (15) | 0.0162 (14) | 0.0061 (14) |
C10 | 0.059 (2) | 0.091 (3) | 0.0414 (19) | −0.026 (2) | 0.0271 (17) | −0.0088 (19) |
C11 | 0.063 (2) | 0.091 (3) | 0.0405 (19) | −0.019 (2) | 0.0258 (18) | −0.0102 (19) |
C12 | 0.0414 (18) | 0.0491 (19) | 0.0343 (16) | 0.0080 (15) | 0.0156 (14) | 0.0018 (15) |
C13 | 0.059 (2) | 0.075 (3) | 0.0419 (19) | −0.003 (2) | 0.0255 (17) | −0.0034 (18) |
C14 | 0.065 (2) | 0.079 (3) | 0.0402 (19) | −0.005 (2) | 0.0218 (18) | −0.0126 (19) |
C15 | 0.063 (2) | 0.062 (2) | 0.0387 (17) | −0.0085 (19) | 0.0232 (17) | −0.0062 (17) |
C16 | 0.063 (2) | 0.061 (2) | 0.054 (2) | −0.0057 (19) | 0.0278 (18) | −0.0015 (18) |
Geometric parameters (Å, º) top
F1—C5 | 1.338 (4) | C4—C5 | 1.428 (6) |
O1—C1 | 1.280 (4) | C5—C6 | 1.324 (5) |
O2—C1 | 1.209 (4) | C6—H6 | 0.9300 |
O3—C3 | 1.219 (4) | C7—C8 | 1.368 (5) |
O4—C4 | 1.229 (4) | C7—H7 | 0.9300 |
O5—H5 | 0.900 (19) | C8—C9 | 1.378 (5) |
N1—C3 | 1.371 (4) | C8—H8 | 0.9300 |
N1—C6 | 1.374 (4) | C9—C10 | 1.386 (4) |
N1—C2 | 1.455 (4) | C9—C12 | 1.481 (5) |
N2—C4 | 1.371 (4) | C10—C11 | 1.371 (5) |
N2—C3 | 1.371 (4) | C10—H10 | 0.9300 |
N2—H2 | 0.876 (18) | C11—H11 | 0.9300 |
N3—C11 | 1.314 (4) | C12—C15 | 1.378 (5) |
N3—C7 | 1.325 (4) | C12—C13 | 1.392 (4) |
N3—H3 | 0.913 (19) | C13—C14 | 1.370 (5) |
N4—C14 | 1.323 (5) | C13—H13 | 0.9300 |
N4—C16 | 1.331 (4) | C14—H14 | 0.9300 |
C1—C2 | 1.516 (5) | C15—C16 | 1.374 (5) |
C2—H2A | 0.9700 | C15—H15 | 0.9300 |
C2—H2B | 0.9700 | C16—H16 | 0.9300 |
| | | |
C3—N1—C6 | 121.0 (3) | N3—C7—C8 | 121.9 (3) |
C3—N1—C2 | 117.8 (3) | N3—C7—H7 | 119.0 |
C6—N1—C2 | 120.3 (3) | C8—C7—H7 | 119.0 |
C4—N2—C3 | 127.6 (3) | C7—C8—C9 | 120.4 (3) |
C4—N2—H2 | 117 (2) | C7—C8—H8 | 119.8 |
C3—N2—H2 | 115 (2) | C9—C8—H8 | 119.8 |
C11—N3—C7 | 119.3 (3) | C8—C9—C10 | 116.1 (3) |
C11—N3—H3 | 119 (2) | C8—C9—C12 | 123.0 (3) |
C7—N3—H3 | 122 (2) | C10—C9—C12 | 120.9 (3) |
C14—N4—C16 | 116.3 (3) | C11—C10—C9 | 120.7 (3) |
O2—C1—O1 | 125.9 (3) | C11—C10—H10 | 119.7 |
O2—C1—C2 | 120.7 (3) | C9—C10—H10 | 119.7 |
O1—C1—C2 | 113.5 (3) | N3—C11—C10 | 121.6 (3) |
N1—C2—C1 | 112.4 (3) | N3—C11—H11 | 119.2 |
N1—C2—H2A | 109.1 | C10—C11—H11 | 119.2 |
C1—C2—H2A | 109.1 | C15—C12—C13 | 115.8 (3) |
N1—C2—H2B | 109.1 | C15—C12—C9 | 122.0 (3) |
C1—C2—H2B | 109.1 | C13—C12—C9 | 122.2 (3) |
H2A—C2—H2B | 107.8 | C14—C13—C12 | 120.1 (3) |
O3—C3—N2 | 122.1 (3) | C14—C13—H13 | 120.0 |
O3—C3—N1 | 122.6 (3) | C12—C13—H13 | 120.0 |
N2—C3—N1 | 115.3 (3) | N4—C14—C13 | 123.9 (3) |
O4—C4—N2 | 121.7 (4) | N4—C14—H14 | 118.1 |
O4—C4—C5 | 125.7 (4) | C13—C14—H14 | 118.1 |
N2—C4—C5 | 112.6 (3) | C16—C15—C12 | 120.3 (3) |
C6—C5—F1 | 120.3 (4) | C16—C15—H15 | 119.8 |
C6—C5—C4 | 122.3 (3) | C12—C15—H15 | 119.8 |
F1—C5—C4 | 117.3 (4) | N4—C16—C15 | 123.6 (4) |
C5—C6—N1 | 121.1 (4) | N4—C16—H16 | 118.2 |
C5—C6—H6 | 119.5 | C15—C16—H16 | 118.2 |
N1—C6—H6 | 119.5 | | |
| | | |
C3—N1—C2—C1 | 76.3 (4) | C11—N3—C7—C8 | 0.6 (6) |
C6—N1—C2—C1 | −92.8 (4) | N3—C7—C8—C9 | −0.5 (6) |
O2—C1—C2—N1 | 7.5 (5) | C7—C8—C9—C10 | 0.5 (5) |
O1—C1—C2—N1 | −172.4 (3) | C7—C8—C9—C12 | −179.6 (3) |
C4—N2—C3—O3 | −178.6 (3) | C8—C9—C10—C11 | −0.7 (6) |
C4—N2—C3—N1 | 2.1 (5) | C12—C9—C10—C11 | 179.4 (3) |
C6—N1—C3—O3 | 176.5 (3) | C7—N3—C11—C10 | −0.9 (6) |
C2—N1—C3—O3 | 7.4 (5) | C9—C10—C11—N3 | 0.9 (6) |
C6—N1—C3—N2 | −4.2 (4) | C8—C9—C12—C15 | 170.9 (3) |
C2—N1—C3—N2 | −173.3 (3) | C10—C9—C12—C15 | −9.2 (5) |
C3—N2—C4—O4 | −179.0 (3) | C8—C9—C12—C13 | −8.2 (5) |
C3—N2—C4—C5 | 1.0 (5) | C10—C9—C12—C13 | 171.6 (3) |
O4—C4—C5—C6 | 177.8 (4) | C15—C12—C13—C14 | −0.6 (5) |
N2—C4—C5—C6 | −2.3 (5) | C9—C12—C13—C14 | 178.6 (3) |
O4—C4—C5—F1 | −2.5 (6) | C16—N4—C14—C13 | 0.0 (6) |
N2—C4—C5—F1 | 177.5 (3) | C12—C13—C14—N4 | 0.5 (6) |
F1—C5—C6—N1 | −179.4 (3) | C13—C12—C15—C16 | 0.3 (5) |
C4—C5—C6—N1 | 0.3 (6) | C9—C12—C15—C16 | −178.9 (3) |
C3—N1—C6—C5 | 3.2 (5) | C14—N4—C16—C15 | −0.4 (6) |
C2—N1—C6—C5 | 172.0 (3) | C12—C15—C16—N4 | 0.2 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O2 | 0.90 (2) | 1.95 (3) | 2.821 (3) | 162 (5) |
N2—H2···N4i | 0.88 (2) | 1.96 (2) | 2.836 (4) | 174 (3) |
N3—H3···O1 | 0.91 (2) | 1.65 (2) | 2.564 (4) | 176 (3) |
Symmetry code: (i) x+1, −y, z+1/2. |