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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018593/sj6098sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018593/sj6098Isup2.hkl
Contains datablock I

CCDC reference: 277786

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](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

Computing details top

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·C10H6O8Z = 1
Mr = 820.66F(000) = 424
Triclinic, P1Dx = 1.580 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.090 (2) ÅCell parameters from 5020 reflections
b = 9.576 (2) Åθ = 1.8–26.4°
c = 11.456 (3) ŵ = 0.13 mm1
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 tubeRint = 0.041
Graphite monochromatorθmax = 26.4°, θmin = 1.8°
Detector resolution: 9 pixels mm-1h = 910
ω scansk = 118
5020 measured reflectionsl = 1414
3434 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H 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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
N10.0444 (3)0.2285 (2)0.84236 (19)0.0482 (6)
N20.3301 (3)0.6861 (2)0.95212 (17)0.0468 (6)
O11.1695 (3)0.37405 (19)1.52091 (15)0.0672 (7)
O21.1196 (3)0.33555 (18)1.32990 (15)0.0665 (6)
O30.8679 (3)0.03762 (18)1.18062 (14)0.0659 (6)
O40.7838 (3)0.20769 (19)1.26587 (16)0.0571 (6)
O51.4420 (3)0.62257 (18)1.63437 (17)0.0649 (6)
O61.2829 (3)0.63929 (17)1.46631 (15)0.0679 (6)
O71.3928 (2)1.22245 (18)1.22155 (16)0.0643 (6)
O81.2750 (3)1.00378 (18)1.20185 (15)0.0704 (6)
C10.4404 (4)0.7904 (3)1.0056 (2)0.0586 (8)
H1B0.46860.87480.96190.070*
C20.5146 (4)0.7808 (3)1.1210 (2)0.0557 (7)
H2B0.59150.85641.15410.067*
C30.4731 (4)0.6577 (3)1.1861 (2)0.0560 (8)
H3A0.52040.64771.26480.067*
C40.3594 (3)0.5484 (3)1.1325 (2)0.0500 (7)
H4A0.32820.46411.17560.060*
C50.2917 (3)0.5638 (3)1.01515 (19)0.0370 (6)
C60.1751 (3)0.4463 (2)0.95408 (19)0.0347 (6)
C70.1139 (3)0.3215 (2)1.0157 (2)0.0454 (7)
H7A0.14710.31081.09670.055*
C80.0058 (3)0.2150 (3)0.9578 (2)0.0498 (7)
H8A0.03330.13180.99970.060*
C90.0098 (4)0.3451 (3)0.7797 (2)0.0560 (8)
H9A0.02760.35240.69910.067*
C100.1201 (3)0.4546 (3)0.8326 (2)0.0492 (7)
H10A0.15890.53520.78750.059*
C110.8649 (3)0.1005 (2)1.2662 (2)0.0365 (6)
C120.9405 (3)0.0543 (2)1.38828 (18)0.0315 (5)
C131.0490 (3)0.1439 (2)1.46658 (18)0.0318 (6)
C141.1160 (3)0.2951 (2)1.4313 (2)0.0393 (6)
C151.1070 (3)0.0882 (2)1.57823 (18)0.0345 (6)
H15A1.17910.14771.63150.041*
C161.3883 (3)0.6946 (2)1.5446 (2)0.0422 (6)
C171.4543 (3)0.8528 (2)1.53092 (19)0.0350 (6)
C181.3992 (3)0.9146 (2)1.42150 (19)0.0381 (6)
H18A1.32990.85541.36670.046*
C191.4389 (3)1.0573 (2)1.38725 (19)0.0344 (6)
C201.3617 (3)1.0960 (3)1.2621 (2)0.0401 (6)
HN10.129 (4)0.141 (3)0.805 (2)0.083 (9)*
HO40.758 (4)0.241 (3)1.192 (3)0.095 (11)*
HO51.519 (4)0.688 (3)1.699 (3)0.094 (10)*
HO11.215 (4)0.468 (4)1.494 (3)0.133 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0625 (16)0.0330 (13)0.0456 (13)0.0022 (11)0.0033 (12)0.0020 (11)
N20.0599 (15)0.0326 (12)0.0407 (12)0.0006 (11)0.0019 (11)0.0067 (10)
O10.1173 (19)0.0273 (11)0.0428 (11)0.0189 (11)0.0043 (11)0.0016 (9)
O20.1030 (17)0.0439 (12)0.0395 (11)0.0144 (10)0.0071 (11)0.0134 (9)
O30.1137 (18)0.0531 (12)0.0319 (10)0.0288 (12)0.0056 (10)0.0045 (9)
O40.0830 (15)0.0480 (12)0.0383 (11)0.0237 (10)0.0071 (10)0.0094 (9)
O50.0860 (16)0.0266 (10)0.0660 (13)0.0020 (10)0.0269 (12)0.0090 (9)
O60.1038 (17)0.0279 (10)0.0510 (12)0.0203 (10)0.0165 (11)0.0041 (8)
O70.0801 (15)0.0321 (11)0.0643 (12)0.0013 (10)0.0263 (11)0.0119 (9)
O80.1030 (18)0.0420 (12)0.0464 (11)0.0202 (11)0.0130 (11)0.0006 (9)
C10.076 (2)0.0376 (16)0.0516 (17)0.0084 (14)0.0001 (16)0.0061 (13)
C20.063 (2)0.0411 (17)0.0535 (17)0.0012 (14)0.0102 (15)0.0058 (13)
C30.067 (2)0.0491 (18)0.0449 (16)0.0099 (15)0.0128 (14)0.0015 (13)
C40.0620 (19)0.0347 (15)0.0458 (16)0.0043 (13)0.0068 (14)0.0077 (12)
C50.0407 (15)0.0319 (14)0.0381 (14)0.0096 (11)0.0026 (12)0.0029 (11)
C60.0367 (15)0.0299 (13)0.0377 (13)0.0101 (11)0.0022 (11)0.0013 (10)
C70.0622 (19)0.0344 (15)0.0349 (13)0.0032 (13)0.0008 (13)0.0056 (11)
C80.067 (2)0.0322 (15)0.0464 (16)0.0024 (13)0.0087 (15)0.0081 (12)
C90.081 (2)0.0411 (17)0.0387 (15)0.0004 (15)0.0013 (15)0.0038 (13)
C100.067 (2)0.0346 (15)0.0382 (15)0.0018 (13)0.0005 (14)0.0077 (12)
C110.0478 (16)0.0240 (13)0.0322 (13)0.0018 (11)0.0006 (12)0.0050 (10)
C120.0408 (15)0.0218 (12)0.0302 (12)0.0031 (10)0.0053 (11)0.0048 (10)
C130.0388 (15)0.0219 (13)0.0318 (12)0.0009 (10)0.0031 (11)0.0036 (9)
C140.0468 (17)0.0262 (14)0.0378 (14)0.0036 (11)0.0033 (12)0.0023 (11)
C150.0433 (15)0.0256 (13)0.0301 (12)0.0008 (11)0.0022 (11)0.0018 (10)
C160.0539 (18)0.0252 (14)0.0427 (15)0.0020 (12)0.0016 (13)0.0011 (12)
C170.0415 (16)0.0221 (13)0.0397 (13)0.0014 (11)0.0051 (12)0.0007 (10)
C180.0421 (16)0.0272 (14)0.0401 (14)0.0032 (11)0.0010 (12)0.0049 (10)
C190.0375 (15)0.0235 (13)0.0404 (13)0.0015 (11)0.0055 (11)0.0021 (10)
C200.0414 (16)0.0295 (14)0.0454 (15)0.0020 (12)0.0007 (12)0.0026 (12)
Geometric parameters (Å, º) top
N1—C91.325 (3)C5—C61.479 (3)
N1—C81.328 (3)C6—C71.394 (3)
N1—HN11.06 (3)C6—C101.397 (3)
N2—C11.335 (3)C7—C81.362 (3)
N2—C51.343 (3)C7—H7A0.9300
O1—C141.296 (3)C8—H8A0.9300
O1—HO10.96 (4)C9—C101.366 (3)
O2—C141.199 (3)C9—H9A0.9300
O3—C111.193 (3)C10—H10A0.9300
O4—C111.312 (3)C11—C121.508 (3)
O4—HO40.89 (3)C12—C131.387 (3)
O5—C161.260 (3)C12—C15i1.392 (3)
O5—HO51.06 (3)C13—C151.395 (3)
O6—C161.222 (3)C13—C141.502 (3)
O7—C201.260 (2)C15—C12i1.392 (3)
O8—C201.215 (3)C15—H15A0.9300
C1—C21.371 (3)C16—C171.520 (3)
C1—H1B0.9300C17—C181.391 (3)
C2—C31.366 (3)C17—C19ii1.407 (3)
C2—H2B0.9300C18—C191.388 (3)
C3—C41.380 (4)C18—H18A0.9300
C3—H3A0.9300C19—C17ii1.407 (3)
C4—C51.381 (3)C19—C201.523 (3)
C4—H4A0.9300
C9—N1—C8121.2 (2)C9—C10—C6120.4 (2)
C9—N1—HN1122.8 (14)C9—C10—H10A119.8
C8—N1—HN1116.0 (14)C6—C10—H10A119.8
C1—N2—C5117.7 (2)O3—C11—O4124.0 (2)
C14—O1—HO1109.8 (19)O3—C11—C12122.6 (2)
C11—O4—HO4109.7 (18)O4—C11—C12113.1 (2)
C16—O5—HO5111.8 (15)C13—C12—C15i119.80 (19)
N2—C1—C2124.1 (2)C13—C12—C11124.40 (19)
N2—C1—H1B118.0C15i—C12—C11115.8 (2)
C2—C1—H1B118.0C12—C13—C15118.66 (19)
C3—C2—C1118.4 (3)C12—C13—C14121.85 (19)
C3—C2—H2B120.8C15—C13—C14119.3 (2)
C1—C2—H2B120.8O2—C14—O1124.7 (2)
C2—C3—C4118.5 (2)O2—C14—C13122.3 (2)
C2—C3—H3A120.8O1—C14—C13113.0 (2)
C4—C3—H3A120.8C12i—C15—C13121.5 (2)
C3—C4—C5120.3 (2)C12i—C15—H15A119.2
C3—C4—H4A119.9C13—C15—H15A119.2
C5—C4—H4A119.9O6—C16—O5121.1 (2)
N2—C5—C4121.0 (2)O6—C16—C17118.3 (2)
N2—C5—C6117.5 (2)O5—C16—C17120.6 (2)
C4—C5—C6121.4 (2)C18—C17—C19ii117.0 (2)
C7—C6—C10116.6 (2)C18—C17—C16114.0 (2)
C7—C6—C5121.3 (2)C19ii—C17—C16129.0 (2)
C10—C6—C5122.1 (2)C19—C18—C17125.5 (2)
C8—C7—C6120.3 (2)C19—C18—H18A117.3
C8—C7—H7A119.8C17—C18—H18A117.3
C6—C7—H7A119.8C18—C19—C17ii117.58 (19)
N1—C8—C7120.8 (2)C18—C19—C20114.4 (2)
N1—C8—H8A119.6C17ii—C19—C20128.0 (2)
C7—C8—H8A119.6O8—C20—O7121.1 (2)
N1—C9—C10120.6 (2)O8—C20—C19119.4 (2)
N1—C9—H9A119.7O7—C20—C19119.5 (2)
C10—C9—H9A119.7
C5—N2—C1—C20.9 (4)O4—C11—C12—C15i124.6 (2)
N2—C1—C2—C30.5 (4)C15i—C12—C13—C150.5 (4)
C1—C2—C3—C40.5 (4)C11—C12—C13—C15178.5 (2)
C2—C3—C4—C50.9 (4)C15i—C12—C13—C14174.7 (2)
C1—N2—C5—C42.3 (4)C11—C12—C13—C146.4 (3)
C1—N2—C5—C6177.5 (2)C12—C13—C14—O220.9 (4)
C3—C4—C5—N22.3 (4)C15—C13—C14—O2154.2 (2)
C3—C4—C5—C6177.4 (2)C12—C13—C14—O1159.8 (2)
N2—C5—C6—C7172.9 (2)C15—C13—C14—O125.1 (3)
C4—C5—C6—C77.3 (4)C12—C13—C15—C12i0.5 (4)
N2—C5—C6—C106.8 (3)C14—C13—C15—C12i174.8 (2)
C4—C5—C6—C10172.9 (2)O6—C16—C17—C187.0 (3)
C10—C6—C7—C80.2 (4)O5—C16—C17—C18172.7 (2)
C5—C6—C7—C8179.6 (2)O6—C16—C17—C19ii172.9 (2)
C9—N1—C8—C70.6 (4)O5—C16—C17—C19ii7.4 (4)
C6—C7—C8—N10.6 (4)C19ii—C17—C18—C190.9 (4)
C8—N1—C9—C100.3 (4)C16—C17—C18—C19179.0 (2)
N1—C9—C10—C61.2 (4)C17—C18—C19—C17ii0.9 (4)
C7—C6—C10—C91.0 (4)C17—C18—C19—C20179.8 (2)
C5—C6—C10—C9178.7 (2)C18—C19—C20—O80.7 (3)
O3—C11—C12—C13131.2 (3)C17ii—C19—C20—O8178.1 (2)
O4—C11—C12—C1354.4 (3)C18—C19—C20—O7178.6 (2)
O3—C11—C12—C15i49.8 (3)C17ii—C19—C20—O70.2 (4)
Symmetry codes: (i) x2, y, z+3; (ii) x3, y+2, z+3.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O8iii1.06 (3)1.66 (3)2.665 (3)158 (2)
O4—HO4···N2iii0.89 (3)1.84 (3)2.717 (3)170 (3)
O5—HO5···O7ii1.06 (3)1.33 (3)2.391 (3)175 (3)
O1—HO1···O60.96 (4)1.66 (4)2.607 (2)171 (3)
Symmetry codes: (ii) x3, y+2, z+3; (iii) x1, y+1, z+2.
 

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