The title organic salt, 2C10H9N2+·C10H4O82-·C10H6O8 or 2(H-2,4'bpy)(H2bta)·H4bta (where H-2,4'bpy is the 2,4'-bipyridine cation, H2bta is the 2,5-dicarboxybenzene-1,4-carboxylate anion and H4bta is the benzene-1,2,4,5-tetracarboxylic acid molecule), crystallizes with both the H2bta dianion and the H4bta molecule lying about inversion centres in the triclinic unit cell. This organic salt is formed by an extensive and complex hydrogen-bonding network containing both homo- and heteronuclear neutral and ionic interactions.
Supporting information
CCDC reference: 277786
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.116
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.24 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.71
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.21
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.14
PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1 - HN1 ... 1.06 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C10 H6 O8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C10 H4 O8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C10 H9 N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); 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: XP (Bruker 1998); software used to prepare material for publication: SHELXL97.
Bis(2,4'-bipyridin-1'-ium) 2,5-dicarboxybenzene-1,4-carboxylate
benzene-1,2,4,5-tetracarboxylic acid
top
Crystal data top
2C10H9N2+·C10H4O82−·C10H6O8 | Z = 1 |
Mr = 820.66 | F(000) = 424 |
Triclinic, P1 | Dx = 1.580 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.090 (2) Å | Cell parameters from 5020 reflections |
b = 9.576 (2) Å | θ = 1.8–26.4° |
c = 11.456 (3) Å | µ = 0.13 mm−1 |
α = 85.739 (4)° | T = 153 K |
β = 81.378 (4)° | Plate, brown |
γ = 79.820 (5)° | 0.21 × 0.17 × 0.09 mm |
V = 862.6 (4) Å3 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 26.4°, θmin = 1.8° |
Detector resolution: 9 pixels mm-1 | h = −9→10 |
ω scans | k = −11→8 |
5020 measured reflections | l = −14→14 |
3434 independent reflections | |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0436P)2] where P = (Fo2 + 2Fc2)/3 |
3434 reflections | (Δ/σ)max < 0.001 |
287 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.18 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 | |
N1 | 0.0444 (3) | 0.2285 (2) | 0.84236 (19) | 0.0482 (6) | |
N2 | −0.3301 (3) | 0.6861 (2) | 0.95212 (17) | 0.0468 (6) | |
O1 | −1.1695 (3) | 0.37405 (19) | 1.52091 (15) | 0.0672 (7) | |
O2 | −1.1196 (3) | 0.33555 (18) | 1.32990 (15) | 0.0665 (6) | |
O3 | −0.8679 (3) | 0.03762 (18) | 1.18062 (14) | 0.0659 (6) | |
O4 | −0.7838 (3) | 0.20769 (19) | 1.26587 (16) | 0.0571 (6) | |
O5 | −1.4420 (3) | 0.62257 (18) | 1.63437 (17) | 0.0649 (6) | |
O6 | −1.2829 (3) | 0.63929 (17) | 1.46631 (15) | 0.0679 (6) | |
O7 | −1.3928 (2) | 1.22245 (18) | 1.22155 (16) | 0.0643 (6) | |
O8 | −1.2750 (3) | 1.00378 (18) | 1.20185 (15) | 0.0704 (6) | |
C1 | −0.4404 (4) | 0.7904 (3) | 1.0056 (2) | 0.0586 (8) | |
H1B | −0.4686 | 0.8748 | 0.9619 | 0.070* | |
C2 | −0.5146 (4) | 0.7808 (3) | 1.1210 (2) | 0.0557 (7) | |
H2B | −0.5915 | 0.8564 | 1.1541 | 0.067* | |
C3 | −0.4731 (4) | 0.6577 (3) | 1.1861 (2) | 0.0560 (8) | |
H3A | −0.5204 | 0.6477 | 1.2648 | 0.067* | |
C4 | −0.3594 (3) | 0.5484 (3) | 1.1325 (2) | 0.0500 (7) | |
H4A | −0.3282 | 0.4641 | 1.1756 | 0.060* | |
C5 | −0.2917 (3) | 0.5638 (3) | 1.01515 (19) | 0.0370 (6) | |
C6 | −0.1751 (3) | 0.4463 (2) | 0.95408 (19) | 0.0347 (6) | |
C7 | −0.1139 (3) | 0.3215 (2) | 1.0157 (2) | 0.0454 (7) | |
H7A | −0.1471 | 0.3108 | 1.0967 | 0.055* | |
C8 | −0.0058 (3) | 0.2150 (3) | 0.9578 (2) | 0.0498 (7) | |
H8A | 0.0333 | 0.1318 | 0.9997 | 0.060* | |
C9 | −0.0098 (4) | 0.3451 (3) | 0.7797 (2) | 0.0560 (8) | |
H9A | 0.0276 | 0.3524 | 0.6991 | 0.067* | |
C10 | −0.1201 (3) | 0.4546 (3) | 0.8326 (2) | 0.0492 (7) | |
H10A | −0.1589 | 0.5352 | 0.7875 | 0.059* | |
C11 | −0.8649 (3) | 0.1005 (2) | 1.2662 (2) | 0.0365 (6) | |
C12 | −0.9405 (3) | 0.0543 (2) | 1.38828 (18) | 0.0315 (5) | |
C13 | −1.0490 (3) | 0.1439 (2) | 1.46658 (18) | 0.0318 (6) | |
C14 | −1.1160 (3) | 0.2951 (2) | 1.4313 (2) | 0.0393 (6) | |
C15 | −1.1070 (3) | 0.0882 (2) | 1.57823 (18) | 0.0345 (6) | |
H15A | −1.1791 | 0.1477 | 1.6315 | 0.041* | |
C16 | −1.3883 (3) | 0.6946 (2) | 1.5446 (2) | 0.0422 (6) | |
C17 | −1.4543 (3) | 0.8528 (2) | 1.53092 (19) | 0.0350 (6) | |
C18 | −1.3992 (3) | 0.9146 (2) | 1.42150 (19) | 0.0381 (6) | |
H18A | −1.3299 | 0.8554 | 1.3667 | 0.046* | |
C19 | −1.4389 (3) | 1.0573 (2) | 1.38725 (19) | 0.0344 (6) | |
C20 | −1.3617 (3) | 1.0960 (3) | 1.2621 (2) | 0.0401 (6) | |
HN1 | 0.129 (4) | 0.141 (3) | 0.805 (2) | 0.083 (9)* | |
HO4 | −0.758 (4) | 0.241 (3) | 1.192 (3) | 0.095 (11)* | |
HO5 | −1.519 (4) | 0.688 (3) | 1.699 (3) | 0.094 (10)* | |
HO1 | −1.215 (4) | 0.468 (4) | 1.494 (3) | 0.133 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0625 (16) | 0.0330 (13) | 0.0456 (13) | −0.0022 (11) | −0.0033 (12) | −0.0020 (11) |
N2 | 0.0599 (15) | 0.0326 (12) | 0.0407 (12) | 0.0006 (11) | 0.0019 (11) | 0.0067 (10) |
O1 | 0.1173 (19) | 0.0273 (11) | 0.0428 (11) | 0.0189 (11) | −0.0043 (11) | 0.0016 (9) |
O2 | 0.1030 (17) | 0.0439 (12) | 0.0395 (11) | 0.0144 (10) | −0.0071 (11) | 0.0134 (9) |
O3 | 0.1137 (18) | 0.0531 (12) | 0.0319 (10) | −0.0288 (12) | 0.0056 (10) | −0.0045 (9) |
O4 | 0.0830 (15) | 0.0480 (12) | 0.0383 (11) | −0.0237 (10) | 0.0071 (10) | 0.0094 (9) |
O5 | 0.0860 (16) | 0.0266 (10) | 0.0660 (13) | −0.0020 (10) | 0.0269 (12) | 0.0090 (9) |
O6 | 0.1038 (17) | 0.0279 (10) | 0.0510 (12) | 0.0203 (10) | 0.0165 (11) | 0.0041 (8) |
O7 | 0.0801 (15) | 0.0321 (11) | 0.0643 (12) | −0.0013 (10) | 0.0263 (11) | 0.0119 (9) |
O8 | 0.1030 (18) | 0.0420 (12) | 0.0464 (11) | 0.0202 (11) | 0.0130 (11) | 0.0006 (9) |
C1 | 0.076 (2) | 0.0376 (16) | 0.0516 (17) | 0.0084 (14) | −0.0001 (16) | 0.0061 (13) |
C2 | 0.063 (2) | 0.0411 (17) | 0.0535 (17) | 0.0012 (14) | 0.0102 (15) | −0.0058 (13) |
C3 | 0.067 (2) | 0.0491 (18) | 0.0449 (16) | −0.0099 (15) | 0.0128 (14) | 0.0015 (13) |
C4 | 0.0620 (19) | 0.0347 (15) | 0.0458 (16) | −0.0043 (13) | 0.0068 (14) | 0.0077 (12) |
C5 | 0.0407 (15) | 0.0319 (14) | 0.0381 (14) | −0.0096 (11) | −0.0026 (12) | 0.0029 (11) |
C6 | 0.0367 (15) | 0.0299 (13) | 0.0377 (13) | −0.0101 (11) | −0.0022 (11) | 0.0013 (10) |
C7 | 0.0622 (19) | 0.0344 (15) | 0.0349 (13) | −0.0032 (13) | −0.0008 (13) | 0.0056 (11) |
C8 | 0.067 (2) | 0.0322 (15) | 0.0464 (16) | −0.0024 (13) | −0.0087 (15) | 0.0081 (12) |
C9 | 0.081 (2) | 0.0411 (17) | 0.0387 (15) | 0.0004 (15) | 0.0013 (15) | 0.0038 (13) |
C10 | 0.067 (2) | 0.0346 (15) | 0.0382 (15) | 0.0018 (13) | −0.0005 (14) | 0.0077 (12) |
C11 | 0.0478 (16) | 0.0240 (13) | 0.0322 (13) | 0.0018 (11) | −0.0006 (12) | 0.0050 (10) |
C12 | 0.0408 (15) | 0.0218 (12) | 0.0302 (12) | −0.0031 (10) | −0.0053 (11) | 0.0048 (10) |
C13 | 0.0388 (15) | 0.0219 (13) | 0.0318 (12) | −0.0009 (10) | −0.0031 (11) | 0.0036 (9) |
C14 | 0.0468 (17) | 0.0262 (14) | 0.0378 (14) | 0.0036 (11) | 0.0033 (12) | 0.0023 (11) |
C15 | 0.0433 (15) | 0.0256 (13) | 0.0301 (12) | 0.0008 (11) | 0.0022 (11) | −0.0018 (10) |
C16 | 0.0539 (18) | 0.0252 (14) | 0.0427 (15) | 0.0020 (12) | −0.0016 (13) | −0.0011 (12) |
C17 | 0.0415 (16) | 0.0221 (13) | 0.0397 (13) | −0.0014 (11) | −0.0051 (12) | −0.0007 (10) |
C18 | 0.0421 (16) | 0.0272 (14) | 0.0401 (14) | 0.0032 (11) | 0.0010 (12) | −0.0049 (10) |
C19 | 0.0375 (15) | 0.0235 (13) | 0.0404 (13) | −0.0015 (11) | −0.0055 (11) | 0.0021 (10) |
C20 | 0.0414 (16) | 0.0295 (14) | 0.0454 (15) | −0.0020 (12) | −0.0007 (12) | 0.0026 (12) |
Geometric parameters (Å, º) top
N1—C9 | 1.325 (3) | C5—C6 | 1.479 (3) |
N1—C8 | 1.328 (3) | C6—C7 | 1.394 (3) |
N1—HN1 | 1.06 (3) | C6—C10 | 1.397 (3) |
N2—C1 | 1.335 (3) | C7—C8 | 1.362 (3) |
N2—C5 | 1.343 (3) | C7—H7A | 0.9300 |
O1—C14 | 1.296 (3) | C8—H8A | 0.9300 |
O1—HO1 | 0.96 (4) | C9—C10 | 1.366 (3) |
O2—C14 | 1.199 (3) | C9—H9A | 0.9300 |
O3—C11 | 1.193 (3) | C10—H10A | 0.9300 |
O4—C11 | 1.312 (3) | C11—C12 | 1.508 (3) |
O4—HO4 | 0.89 (3) | C12—C13 | 1.387 (3) |
O5—C16 | 1.260 (3) | C12—C15i | 1.392 (3) |
O5—HO5 | 1.06 (3) | C13—C15 | 1.395 (3) |
O6—C16 | 1.222 (3) | C13—C14 | 1.502 (3) |
O7—C20 | 1.260 (2) | C15—C12i | 1.392 (3) |
O8—C20 | 1.215 (3) | C15—H15A | 0.9300 |
C1—C2 | 1.371 (3) | C16—C17 | 1.520 (3) |
C1—H1B | 0.9300 | C17—C18 | 1.391 (3) |
C2—C3 | 1.366 (3) | C17—C19ii | 1.407 (3) |
C2—H2B | 0.9300 | C18—C19 | 1.388 (3) |
C3—C4 | 1.380 (4) | C18—H18A | 0.9300 |
C3—H3A | 0.9300 | C19—C17ii | 1.407 (3) |
C4—C5 | 1.381 (3) | C19—C20 | 1.523 (3) |
C4—H4A | 0.9300 | | |
| | | |
C9—N1—C8 | 121.2 (2) | C9—C10—C6 | 120.4 (2) |
C9—N1—HN1 | 122.8 (14) | C9—C10—H10A | 119.8 |
C8—N1—HN1 | 116.0 (14) | C6—C10—H10A | 119.8 |
C1—N2—C5 | 117.7 (2) | O3—C11—O4 | 124.0 (2) |
C14—O1—HO1 | 109.8 (19) | O3—C11—C12 | 122.6 (2) |
C11—O4—HO4 | 109.7 (18) | O4—C11—C12 | 113.1 (2) |
C16—O5—HO5 | 111.8 (15) | C13—C12—C15i | 119.80 (19) |
N2—C1—C2 | 124.1 (2) | C13—C12—C11 | 124.40 (19) |
N2—C1—H1B | 118.0 | C15i—C12—C11 | 115.8 (2) |
C2—C1—H1B | 118.0 | C12—C13—C15 | 118.66 (19) |
C3—C2—C1 | 118.4 (3) | C12—C13—C14 | 121.85 (19) |
C3—C2—H2B | 120.8 | C15—C13—C14 | 119.3 (2) |
C1—C2—H2B | 120.8 | O2—C14—O1 | 124.7 (2) |
C2—C3—C4 | 118.5 (2) | O2—C14—C13 | 122.3 (2) |
C2—C3—H3A | 120.8 | O1—C14—C13 | 113.0 (2) |
C4—C3—H3A | 120.8 | C12i—C15—C13 | 121.5 (2) |
C3—C4—C5 | 120.3 (2) | C12i—C15—H15A | 119.2 |
C3—C4—H4A | 119.9 | C13—C15—H15A | 119.2 |
C5—C4—H4A | 119.9 | O6—C16—O5 | 121.1 (2) |
N2—C5—C4 | 121.0 (2) | O6—C16—C17 | 118.3 (2) |
N2—C5—C6 | 117.5 (2) | O5—C16—C17 | 120.6 (2) |
C4—C5—C6 | 121.4 (2) | C18—C17—C19ii | 117.0 (2) |
C7—C6—C10 | 116.6 (2) | C18—C17—C16 | 114.0 (2) |
C7—C6—C5 | 121.3 (2) | C19ii—C17—C16 | 129.0 (2) |
C10—C6—C5 | 122.1 (2) | C19—C18—C17 | 125.5 (2) |
C8—C7—C6 | 120.3 (2) | C19—C18—H18A | 117.3 |
C8—C7—H7A | 119.8 | C17—C18—H18A | 117.3 |
C6—C7—H7A | 119.8 | C18—C19—C17ii | 117.58 (19) |
N1—C8—C7 | 120.8 (2) | C18—C19—C20 | 114.4 (2) |
N1—C8—H8A | 119.6 | C17ii—C19—C20 | 128.0 (2) |
C7—C8—H8A | 119.6 | O8—C20—O7 | 121.1 (2) |
N1—C9—C10 | 120.6 (2) | O8—C20—C19 | 119.4 (2) |
N1—C9—H9A | 119.7 | O7—C20—C19 | 119.5 (2) |
C10—C9—H9A | 119.7 | | |
| | | |
C5—N2—C1—C2 | 0.9 (4) | O4—C11—C12—C15i | −124.6 (2) |
N2—C1—C2—C3 | 0.5 (4) | C15i—C12—C13—C15 | 0.5 (4) |
C1—C2—C3—C4 | −0.5 (4) | C11—C12—C13—C15 | −178.5 (2) |
C2—C3—C4—C5 | −0.9 (4) | C15i—C12—C13—C14 | −174.7 (2) |
C1—N2—C5—C4 | −2.3 (4) | C11—C12—C13—C14 | 6.4 (3) |
C1—N2—C5—C6 | 177.5 (2) | C12—C13—C14—O2 | 20.9 (4) |
C3—C4—C5—N2 | 2.3 (4) | C15—C13—C14—O2 | −154.2 (2) |
C3—C4—C5—C6 | −177.4 (2) | C12—C13—C14—O1 | −159.8 (2) |
N2—C5—C6—C7 | 172.9 (2) | C15—C13—C14—O1 | 25.1 (3) |
C4—C5—C6—C7 | −7.3 (4) | C12—C13—C15—C12i | −0.5 (4) |
N2—C5—C6—C10 | −6.8 (3) | C14—C13—C15—C12i | 174.8 (2) |
C4—C5—C6—C10 | 172.9 (2) | O6—C16—C17—C18 | 7.0 (3) |
C10—C6—C7—C8 | 0.2 (4) | O5—C16—C17—C18 | −172.7 (2) |
C5—C6—C7—C8 | −179.6 (2) | O6—C16—C17—C19ii | −172.9 (2) |
C9—N1—C8—C7 | −0.6 (4) | O5—C16—C17—C19ii | 7.4 (4) |
C6—C7—C8—N1 | 0.6 (4) | C19ii—C17—C18—C19 | 0.9 (4) |
C8—N1—C9—C10 | −0.3 (4) | C16—C17—C18—C19 | −179.0 (2) |
N1—C9—C10—C6 | 1.2 (4) | C17—C18—C19—C17ii | −0.9 (4) |
C7—C6—C10—C9 | −1.0 (4) | C17—C18—C19—C20 | −179.8 (2) |
C5—C6—C10—C9 | 178.7 (2) | C18—C19—C20—O8 | 0.7 (3) |
O3—C11—C12—C13 | −131.2 (3) | C17ii—C19—C20—O8 | −178.1 (2) |
O4—C11—C12—C13 | 54.4 (3) | C18—C19—C20—O7 | 178.6 (2) |
O3—C11—C12—C15i | 49.8 (3) | C17ii—C19—C20—O7 | −0.2 (4) |
Symmetry codes: (i) −x−2, −y, −z+3; (ii) −x−3, −y+2, −z+3. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O8iii | 1.06 (3) | 1.66 (3) | 2.665 (3) | 158 (2) |
O4—HO4···N2iii | 0.89 (3) | 1.84 (3) | 2.717 (3) | 170 (3) |
O5—HO5···O7ii | 1.06 (3) | 1.33 (3) | 2.391 (3) | 175 (3) |
O1—HO1···O6 | 0.96 (4) | 1.66 (4) | 2.607 (2) | 171 (3) |
Symmetry codes: (ii) −x−3, −y+2, −z+3; (iii) −x−1, −y+1, −z+2. |