Literature DB >> 21589461

4-(4-Pyrid-yl)pyridinium 3-amino-5-carb-oxy-2,4,6-triiodo-benzoate-5-amino-2,4,6-triiodo-isophthalic acid (1/1).

Kou-Lin Zhang, Guo-Wang Diao, Seik Weng Ng.   

Abstract

In the title ammonium carboxyl-ate-carb-oxy-lic acid co-cystal, C(10)H(9)N(2) (+)·C(8)H(3)I(3)NO(4) (-.)C(8)H(4)I(3)NO(4), the carboxyl-ate anion and carb-oxy-lic acid mol-ecule are linked by O-H⋯O and N-H⋯O n class="Chemical">hydrogen bonds to form a chain running along the c axis of the monoclinic unit cell. The chains are linked by pyridinum and pyridine N-H⋯O hydrogen bonds, generating a layer motif. O-H⋯N and O-H⋯O hydrogen bonds are also observed.

Entities:  

Year:  2010        PMID: 21589461      PMCID: PMC3011675          DOI: 10.1107/S1600536810045514

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the crystal structure of 5-amino-2,4,6-triiodo­isophthalic acid monohydrate, see: Beck & Sheldrick (2008 ▶).

Experimental

Crystal data

C10H9N2C8H3I3NO4 −·C8H4I3NO4 M = 1273.83 Monoclinic, a = 7.7388 (4) Å b = 34.2377 (19) Å c = 13.0739 (7) Å β = 106.506 (1)° V = 3321.3 (3) Å3 Z = 4 Mo Kα radiation μ = 5.66 mm−1 T = 295 K 0.08 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.660, T max = 0.805 28196 measured reflections 7506 independent reflections 6365 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.082 S = 1.03 7506 reflections 429 parameters 8 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 1.25 e Å−3 Δρmin = −1.26 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045514/nk2065sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045514/nk2065Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C10H9N2+·C8H3I3NO4·C8H4I3NO4F(000) = 2328
Mr = 1273.83Dx = 2.547 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9939 reflections
a = 7.7388 (4) Åθ = 2.4–27.4°
b = 34.2377 (19) ŵ = 5.66 mm1
c = 13.0739 (7) ÅT = 295 K
β = 106.506 (1)°Prism, yellow
V = 3321.3 (3) Å30.08 × 0.06 × 0.04 mm
Z = 4
Bruker SMART APEX diffractometer7506 independent reflections
Radiation source: fine-focus sealed tube6365 reflections with I > 2σ(I)
graphiteRint = 0.037
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.660, Tmax = 0.805k = −44→44
28196 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0387P)2 + 6.6421P] where P = (Fo2 + 2Fc2)/3
7506 reflections(Δ/σ)max = 0.001
429 parametersΔρmax = 1.25 e Å3
8 restraintsΔρmin = −1.26 e Å3
xyzUiso*/Ueq
I10.89589 (4)0.633599 (10)0.26091 (3)0.03827 (9)
I20.17486 (6)0.713602 (10)0.08490 (4)0.05879 (13)
I30.22245 (5)0.537807 (9)0.07851 (3)0.03820 (9)
I40.63572 (4)0.521651 (8)0.65077 (2)0.03066 (8)
I50.57056 (6)0.666532 (10)0.90690 (3)0.04259 (10)
I60.36084 (5)0.672374 (10)0.42509 (3)0.04230 (10)
O10.6872 (5)0.54473 (9)0.2775 (2)0.0315 (7)
O20.6823 (5)0.54041 (10)0.1070 (3)0.0370 (8)
O30.6689 (6)0.71617 (11)0.1148 (3)0.0430 (9)
H3O0.724 (12)0.7376 (14)0.130 (7)0.12 (4)*
O40.6193 (7)0.72189 (11)0.2738 (3)0.0577 (12)
O50.6413 (5)0.58392 (11)0.4353 (3)0.0368 (8)
H5O0.628 (8)0.5720 (16)0.377 (3)0.055 (19)*
O60.3505 (5)0.56703 (11)0.4066 (3)0.0432 (9)
O70.5332 (5)0.56640 (12)0.9082 (3)0.0394 (8)
H7O0.575 (9)0.5570 (19)0.970 (2)0.07 (2)*
O80.8114 (5)0.56830 (13)0.8926 (3)0.0449 (9)
N10.0653 (6)0.62476 (12)0.0256 (4)0.0362 (9)
H110.004 (7)0.6029 (9)0.018 (4)0.045 (16)*
H12−0.001 (7)0.6455 (11)0.029 (5)0.048 (17)*
N20.4185 (7)0.69823 (12)0.6687 (4)0.0423 (11)
H210.461 (8)0.7106 (16)0.730 (3)0.052 (18)*
H220.412 (8)0.7143 (14)0.615 (3)0.048 (17)*
N30.8284 (5)0.47376 (12)0.3134 (3)0.0324 (9)
H30.787 (8)0.4976 (7)0.299 (5)0.055 (18)*
N41.1535 (6)0.28111 (12)0.3578 (4)0.0399 (10)
C10.6421 (6)0.55702 (12)0.1815 (3)0.0255 (9)
C20.5326 (6)0.59425 (12)0.1600 (3)0.0228 (9)
C30.6155 (6)0.63055 (12)0.1880 (3)0.0241 (9)
C40.5151 (6)0.66494 (12)0.1677 (3)0.0258 (9)
C50.3306 (6)0.66243 (12)0.1171 (4)0.0263 (9)
C60.2431 (6)0.62650 (12)0.0846 (3)0.0262 (9)
C70.3500 (6)0.59272 (12)0.1111 (3)0.0248 (9)
C80.6070 (7)0.70421 (13)0.1925 (4)0.0315 (10)
C90.6552 (6)0.57584 (13)0.8604 (3)0.0256 (9)
C100.5792 (6)0.59878 (13)0.7573 (3)0.0230 (9)
C110.5321 (7)0.63773 (13)0.7594 (3)0.0281 (9)
C120.4688 (6)0.66010 (13)0.6662 (4)0.0282 (9)
C130.4532 (6)0.64080 (13)0.5687 (3)0.0256 (9)
C140.5027 (6)0.60201 (12)0.5647 (3)0.0228 (8)
C150.5677 (6)0.58054 (12)0.6596 (3)0.0244 (9)
C160.4885 (6)0.58222 (13)0.4591 (3)0.0267 (9)
C170.8615 (7)0.45571 (14)0.4059 (4)0.0361 (11)
H170.84340.46890.46410.043*
C180.9221 (7)0.41776 (14)0.4184 (4)0.0329 (10)
H180.94610.40560.48460.040*
C190.9471 (6)0.39770 (12)0.3306 (4)0.0258 (9)
C200.9103 (7)0.41793 (14)0.2341 (4)0.0337 (11)
H200.92570.40570.17370.040*
C210.8514 (7)0.45584 (15)0.2286 (4)0.0375 (11)
H21A0.82710.46920.16410.045*
C221.1572 (7)0.30185 (14)0.4440 (4)0.0393 (12)
H22A1.20630.29070.51090.047*
C231.0905 (7)0.33952 (14)0.4377 (4)0.0381 (12)
H231.09550.35320.49990.046*
C241.0163 (6)0.35702 (13)0.3398 (4)0.0273 (9)
C251.0087 (9)0.33460 (16)0.2503 (5)0.0474 (14)
H250.95640.34460.18230.057*
C261.0804 (9)0.29694 (16)0.2632 (5)0.0505 (15)
H261.07660.28230.20260.061*
U11U22U33U12U13U23
I10.03160 (17)0.04546 (19)0.03463 (18)−0.00668 (14)0.00433 (13)0.00376 (14)
I20.0485 (2)0.02261 (17)0.1008 (4)0.00977 (15)0.0140 (2)0.00154 (18)
I30.0456 (2)0.02220 (15)0.03956 (19)−0.00873 (13)0.00046 (15)0.00157 (12)
I40.04117 (18)0.02040 (14)0.02876 (16)0.00191 (12)0.00727 (13)−0.00067 (11)
I50.0665 (2)0.03696 (18)0.02578 (17)0.00401 (16)0.01550 (16)−0.00919 (13)
I60.0586 (2)0.03503 (18)0.02813 (17)0.00338 (15)0.00399 (15)0.00980 (13)
O10.048 (2)0.0260 (16)0.0220 (16)0.0110 (14)0.0115 (14)0.0039 (12)
O20.055 (2)0.0356 (19)0.0235 (16)0.0134 (16)0.0155 (16)0.0004 (14)
O30.063 (3)0.034 (2)0.036 (2)−0.0227 (18)0.0215 (18)−0.0058 (16)
O40.106 (4)0.032 (2)0.041 (2)−0.021 (2)0.031 (2)−0.0154 (17)
O50.048 (2)0.040 (2)0.0256 (18)−0.0024 (16)0.0162 (16)−0.0078 (15)
O60.047 (2)0.044 (2)0.0331 (19)−0.0068 (17)0.0031 (17)−0.0128 (16)
O70.0347 (19)0.054 (2)0.033 (2)0.0066 (16)0.0138 (16)0.0192 (17)
O80.0283 (19)0.066 (3)0.037 (2)0.0010 (17)0.0044 (15)0.0109 (18)
N10.031 (2)0.027 (2)0.044 (2)−0.0006 (17)0.0019 (19)−0.0031 (19)
N20.073 (3)0.020 (2)0.035 (3)0.011 (2)0.017 (2)0.0015 (18)
N30.031 (2)0.027 (2)0.040 (2)0.0103 (17)0.0100 (18)0.0067 (17)
N40.048 (3)0.024 (2)0.052 (3)0.0102 (18)0.020 (2)0.0028 (19)
C10.032 (2)0.0177 (19)0.026 (2)−0.0002 (17)0.0067 (18)0.0001 (17)
C20.035 (2)0.0186 (19)0.0145 (19)0.0001 (17)0.0065 (17)0.0022 (15)
C30.025 (2)0.028 (2)0.020 (2)−0.0031 (17)0.0066 (17)−0.0006 (17)
C40.040 (3)0.0163 (19)0.023 (2)−0.0027 (17)0.0116 (19)−0.0006 (16)
C50.034 (2)0.0162 (19)0.030 (2)0.0028 (17)0.0112 (19)0.0021 (17)
C60.035 (2)0.023 (2)0.022 (2)0.0023 (18)0.0102 (18)0.0008 (17)
C70.035 (2)0.0157 (18)0.023 (2)−0.0047 (17)0.0080 (18)−0.0014 (16)
C80.044 (3)0.018 (2)0.033 (2)−0.0019 (19)0.011 (2)−0.0022 (18)
C90.033 (3)0.025 (2)0.019 (2)−0.0019 (18)0.0067 (18)−0.0033 (16)
C100.024 (2)0.027 (2)0.018 (2)−0.0044 (17)0.0061 (16)−0.0021 (16)
C110.039 (3)0.025 (2)0.021 (2)−0.0028 (19)0.0092 (19)−0.0037 (17)
C120.034 (3)0.020 (2)0.031 (2)−0.0035 (18)0.009 (2)−0.0039 (17)
C130.030 (2)0.027 (2)0.019 (2)0.0010 (18)0.0044 (17)0.0050 (17)
C140.028 (2)0.0212 (19)0.021 (2)−0.0026 (16)0.0088 (17)−0.0015 (16)
C150.028 (2)0.020 (2)0.025 (2)−0.0013 (16)0.0073 (18)−0.0020 (17)
C160.034 (3)0.023 (2)0.021 (2)0.0009 (18)0.0050 (19)0.0002 (17)
C170.041 (3)0.030 (2)0.039 (3)0.011 (2)0.015 (2)−0.001 (2)
C180.043 (3)0.026 (2)0.032 (2)0.010 (2)0.015 (2)0.0045 (19)
C190.027 (2)0.022 (2)0.029 (2)0.0044 (17)0.0088 (18)0.0023 (17)
C200.044 (3)0.027 (2)0.033 (3)0.003 (2)0.015 (2)0.0045 (19)
C210.046 (3)0.035 (3)0.034 (3)0.007 (2)0.015 (2)0.008 (2)
C220.049 (3)0.026 (2)0.042 (3)0.008 (2)0.010 (2)0.004 (2)
C230.050 (3)0.027 (2)0.038 (3)0.007 (2)0.014 (2)0.003 (2)
C240.026 (2)0.025 (2)0.032 (2)0.0052 (17)0.0108 (19)0.0011 (18)
C250.064 (4)0.037 (3)0.039 (3)0.015 (3)0.011 (3)0.004 (2)
C260.078 (4)0.033 (3)0.041 (3)0.016 (3)0.018 (3)−0.004 (2)
I1—C32.110 (4)C3—C41.394 (6)
I2—C52.100 (4)C4—C51.395 (7)
I3—C72.110 (4)C4—C81.513 (6)
I4—C152.095 (4)C5—C61.410 (6)
I5—C112.111 (4)C6—C71.407 (6)
I6—C132.108 (4)C9—C101.526 (6)
O1—C11.276 (5)C10—C111.385 (6)
O2—C11.241 (5)C10—C151.402 (6)
O3—C81.307 (6)C11—C121.404 (6)
O3—H3O0.84 (1)C12—C131.409 (6)
O4—C81.203 (6)C13—C141.388 (6)
O5—C161.307 (6)C14—C151.406 (6)
O5—H5O0.84 (1)C14—C161.513 (6)
O6—C161.211 (6)C17—C181.375 (6)
O7—C91.313 (6)C17—H170.9300
O7—H7O0.84 (1)C18—C191.398 (6)
O8—C91.190 (6)C18—H180.9300
N1—C61.374 (6)C19—C201.396 (6)
N1—H110.88 (1)C19—C241.485 (6)
N1—H120.88 (1)C20—C211.371 (7)
N2—C121.366 (6)C20—H200.9300
N2—H210.88 (1)C21—H21A0.9300
N2—H220.88 (1)C22—C231.383 (7)
N3—C171.316 (6)C22—H22A0.9300
N3—C211.323 (7)C23—C241.382 (7)
N3—H30.878 (10)C23—H230.9300
N4—C261.322 (7)C24—C251.387 (7)
N4—C221.325 (7)C25—C261.395 (7)
C1—C21.512 (6)C25—H250.9300
C2—C71.376 (6)C26—H260.9300
C2—C31.399 (6)
C8—O3—H3O111 (6)N2—C12—C11122.2 (4)
C16—O5—H5O108 (4)N2—C12—C13121.2 (4)
C9—O7—H7O115 (5)C11—C12—C13116.6 (4)
C6—N1—H11122 (4)C14—C13—C12122.0 (4)
C6—N1—H12116 (4)C14—C13—I6119.0 (3)
H11—N1—H12113 (6)C12—C13—I6119.0 (3)
C12—N2—H21117 (4)C13—C14—C15120.0 (4)
C12—N2—H22122 (4)C13—C14—C16120.9 (4)
H21—N2—H22110 (6)C15—C14—C16119.1 (4)
C17—N3—C21121.0 (4)C10—C15—C14119.0 (4)
C17—N3—H3127 (4)C10—C15—I4121.8 (3)
C21—N3—H3112 (4)C14—C15—I4119.1 (3)
C26—N4—C22118.5 (4)O6—C16—O5126.6 (4)
O2—C1—O1124.1 (4)O6—C16—C14122.2 (4)
O2—C1—C2119.6 (4)O5—C16—C14111.2 (4)
O1—C1—C2116.3 (4)N3—C17—C18121.6 (5)
C7—C2—C3119.3 (4)N3—C17—H17119.2
C7—C2—C1120.1 (4)C18—C17—H17119.2
C3—C2—C1120.6 (4)C17—C18—C19119.2 (4)
C4—C3—C2120.7 (4)C17—C18—H18120.4
C4—C3—I1119.4 (3)C19—C18—H18120.4
C2—C3—I1119.9 (3)C20—C19—C18117.3 (4)
C3—C4—C5118.6 (4)C20—C19—C24121.0 (4)
C3—C4—C8120.5 (4)C18—C19—C24121.7 (4)
C5—C4—C8120.8 (4)C21—C20—C19119.8 (4)
C4—C5—C6122.4 (4)C21—C20—H20120.1
C4—C5—I2119.7 (3)C19—C20—H20120.1
C6—C5—I2117.9 (3)N3—C21—C20121.1 (5)
N1—C6—C7121.8 (4)N3—C21—H21A119.4
N1—C6—C5121.7 (4)C20—C21—H21A119.4
C7—C6—C5116.4 (4)N4—C22—C23122.1 (5)
C2—C7—C6122.5 (4)N4—C22—H22A119.0
C2—C7—I3119.2 (3)C23—C22—H22A119.0
C6—C7—I3118.3 (3)C24—C23—C22120.6 (5)
O4—C8—O3125.1 (4)C24—C23—H23119.7
O4—C8—C4123.4 (4)C22—C23—H23119.7
O3—C8—C4111.4 (4)C23—C24—C25116.6 (4)
O8—C9—O7125.0 (4)C23—C24—C19121.8 (4)
O8—C9—C10121.5 (4)C25—C24—C19121.5 (4)
O7—C9—C10113.5 (4)C24—C25—C26119.3 (5)
C11—C10—C15119.9 (4)C24—C25—H25120.3
C11—C10—C9121.0 (4)C26—C25—H25120.3
C15—C10—C9119.0 (4)N4—C26—C25122.8 (5)
C10—C11—C12122.5 (4)N4—C26—H26118.6
C10—C11—I5119.9 (3)C25—C26—H26118.6
C12—C11—I5117.5 (3)
O2—C1—C2—C776.5 (6)C10—C11—C12—C130.6 (7)
O1—C1—C2—C7−103.4 (5)I5—C11—C12—C13176.7 (3)
O2—C1—C2—C3−102.6 (5)N2—C12—C13—C14−179.6 (5)
O1—C1—C2—C377.5 (5)C11—C12—C13—C14−1.9 (7)
C7—C2—C3—C40.5 (6)N2—C12—C13—I62.7 (6)
C1—C2—C3—C4179.6 (4)C11—C12—C13—I6−179.6 (3)
C7—C2—C3—I1−179.1 (3)C12—C13—C14—C151.2 (7)
C1—C2—C3—I10.0 (5)I6—C13—C14—C15178.9 (3)
C2—C3—C4—C5−1.2 (6)C12—C13—C14—C16−178.6 (4)
I1—C3—C4—C5178.4 (3)I6—C13—C14—C16−1.0 (6)
C2—C3—C4—C8−176.6 (4)C11—C10—C15—C14−2.0 (6)
I1—C3—C4—C83.0 (5)C9—C10—C15—C14−178.1 (4)
C3—C4—C5—C6−0.8 (7)C11—C10—C15—I4−179.7 (3)
C8—C4—C5—C6174.5 (4)C9—C10—C15—I44.2 (6)
C3—C4—C5—I2−179.9 (3)C13—C14—C15—C100.8 (6)
C8—C4—C5—I2−4.5 (6)C16—C14—C15—C10−179.4 (4)
C4—C5—C6—N1−173.5 (4)C13—C14—C15—I4178.6 (3)
I2—C5—C6—N15.6 (6)C16—C14—C15—I4−1.6 (5)
C4—C5—C6—C73.3 (6)C13—C14—C16—O6−86.0 (6)
I2—C5—C6—C7−177.6 (3)C15—C14—C16—O694.1 (6)
C3—C2—C7—C62.2 (6)C13—C14—C16—O594.3 (5)
C1—C2—C7—C6−176.9 (4)C15—C14—C16—O5−85.6 (5)
C3—C2—C7—I3−175.9 (3)C21—N3—C17—C180.5 (8)
C1—C2—C7—I35.1 (5)N3—C17—C18—C19−0.8 (8)
N1—C6—C7—C2172.8 (4)C17—C18—C19—C200.7 (7)
C5—C6—C7—C2−4.0 (6)C17—C18—C19—C24178.6 (5)
N1—C6—C7—I3−9.1 (6)C18—C19—C20—C21−0.3 (7)
C5—C6—C7—I3174.0 (3)C24—C19—C20—C21−178.2 (5)
C3—C4—C8—O4−96.2 (6)C17—N3—C21—C200.0 (8)
C5—C4—C8—O488.5 (7)C19—C20—C21—N30.0 (8)
C3—C4—C8—O384.2 (5)C26—N4—C22—C23−1.3 (9)
C5—C4—C8—O3−91.1 (5)N4—C22—C23—C240.1 (9)
O8—C9—C10—C11−104.2 (6)C22—C23—C24—C251.6 (8)
O7—C9—C10—C1174.8 (5)C22—C23—C24—C19−178.7 (5)
O8—C9—C10—C1571.9 (6)C20—C19—C24—C23165.6 (5)
O7—C9—C10—C15−109.2 (5)C18—C19—C24—C23−12.2 (7)
C15—C10—C11—C121.3 (7)C20—C19—C24—C25−14.8 (7)
C9—C10—C11—C12177.3 (4)C18—C19—C24—C25167.4 (5)
C15—C10—C11—I5−174.7 (3)C23—C24—C25—C26−2.2 (9)
C9—C10—C11—I51.3 (6)C19—C24—C25—C26178.1 (5)
C10—C11—C12—N2178.4 (5)C22—N4—C26—C250.6 (9)
I5—C11—C12—N2−5.5 (6)C24—C25—C26—N41.2 (10)
D—H···AD—HH···AD···AD—H···A
N1—H11···O8i0.88 (1)2.22 (4)2.946 (6)141 (5)
N3—H3···O10.88 (1)1.78 (1)2.651 (5)174 (6)
O3—H3o···N4ii0.84 (1)1.75 (2)2.585 (5)171 (9)
O5—H5o···O10.84 (1)1.77 (3)2.568 (4)159 (6)
O7—H7o···O2iii0.84 (1)1.84 (1)2.679 (5)174 (7)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N1—H11⋯O8i0.88 (1)2.22 (4)2.946 (6)141 (5)
N3—H3⋯O10.88 (1)1.78 (1)2.651 (5)174 (6)
O3—H3o⋯N4ii0.84 (1)1.75 (2)2.585 (5)171 (9)
O5—H5o⋯O10.84 (1)1.77 (3)2.568 (4)159 (6)
O7—H7o⋯O2iii0.84 (1)1.84 (1)2.679 (5)174 (7)

Symmetry codes: (i) ; (ii) ; (iii) .

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  Tobias Beck; George M Sheldrick
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-19
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1.  5-Amino-2,4,6-triiodo-isophthalic acid-4,4'-bipyridine N,N'-dioxide-water (1/1/1).

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