4-(4-Pyrid­yl)pyridinium 3-amino-5-carb­oxy-2,4,6-triiodo­benzoate–5-amino-2,4,6-triiodo­isophthalic acid (1/1)

Zhang, K.-L.; Diao, G.-W.; Ng, S.W.

doi:10.1107/S1600536810045514

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3165

https://doi.org/10.1107/S1600536810045514

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4-(4-Pyridyl)pyridinium 3-amino-5-carboxy-2,4,6-triiodobenzoate–5-amino-2,4,6-triiodoisophthalic acid (1/1)

Kou-Lin Zhang,^a Guo-Wang Diao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 October 2010; accepted 5 November 2010; online 13 November 2010)

In the title ammonium carboxylate–carboxylic acid co-cystal, C₁₀H₉N₂⁺·C₈H₃I₃NO₄^−.C₈H₄I₃NO₄, the carboxylate anion and carboxylic acid molecule are linked by O—H⋯O and N—H⋯O 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.

Related literature

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

Experimental

Crystal data

C₁₀H₉N₂⁺·C₈H₃I₃NO₄⁻·C₈H₄I₃NO₄
M_r = 1273.83
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.03
7506 reflections
429 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.25 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O8ⁱ	0.88 (1)	2.22 (4)	2.946 (6)	141 (5)
N3—H3⋯O1	0.88 (1)	1.78 (1)	2.651 (5)	174 (6)
O3—H3o⋯N4ⁱⁱ	0.84 (1)	1.75 (2)	2.585 (5)	171 (9)
O5—H5o⋯O1	0.84 (1)	1.77 (3)	2.568 (4)	159 (6)
O7—H7o⋯O2ⁱⁱⁱ	0.84 (1)	1.84 (1)	2.679 (5)	174 (7)
Symmetry codes: (i) x-1, y, z-1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045514/nk2065sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045514/nk2065Isup2.hkl

checkCIF report

Comment top

5-Amino-2,4,6-triiodoisophthalic acid exists as a monohydrated compound for which the acid and water molecules are linked by extensive O–H···O, O–H···N and N–H···O hydrogen bonds to form a three-dimensional network (Beck & Sheldrick, 2008). The acid furnishes a small number of coordination compounds. The attempt to synthesize a cadmium derivative that can be linked by 4,4'-bipyridine gave instead the co-crystal, C₁₀H₉N₂⁺C₈H₃NO₄I₃^-.C₈H₄NO₄I₃ (Scheme I, Fig. 1).

The carboxylate anion and carboxylic acid are linked by O–H···O and N–H···O hydrogen bonds to form a chain running along the c-axis of the monoclinic unit cell. The chains are linked by N_pyridinum–H···O and N_pyridyl–H···O hydrogen bonds to generate a layer motif (Fig. 2, Table 1).

Related literature top

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

Experimental top

An aqueous solution of cadmium dichloride 2.5 hydrate (0.023 g, 0.1 mmol) in water (5 ml) was added to a mixture of 5-amino-2,4,6-triiodoisophthalic acid (0.056 g, 0.1 mmol) in water (5 ml) and sodium hydroxide (0.2 ml, 0.5 M). To the solution was added 4,4'-bipyridine (0.016 g, 0.1 mmol) in water (5 ml). The solution was filed; slow evaporation yielded deep yellow crystals were collected (30% yield). CH&N elemental analysis. Calc. for C₂₆H₁₆I₆N₄O₈: C 24.51, H 1.27, N 4.43%; Found: C, 24.43; H, 1.29; N, 4.50%.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₁₀H₉N₂⁺C₈H₃NO₄I₃^-.C₈H₄NO₄I₃ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The hydrogen-bonded layer structure. Each amino group forms only one hydrogen bond; the weaker hydrogen bond is are not shown.

4-(4-Pyridyl)pyridinium 3-amino-5-carboxy-2,4,6-triiodobenzoate–5-amino-2,4,6-triiodoisophthalic acid (1/1) top

Crystal data top

C₁₀H₉N₂⁺·C₈H₃I₃NO₄⁻·C₈H₄I₃NO₄	F(000) = 2328
M_r = 1273.83	D_x = 2.547 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9939 reflections
a = 7.7388 (4) Å	θ = 2.4–27.4°
b = 34.2377 (19) Å	µ = 5.66 mm⁻¹
c = 13.0739 (7) Å	T = 295 K
β = 106.506 (1)°	Prism, yellow
V = 3321.3 (3) Å³	0.08 × 0.06 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	7506 independent reflections
Radiation source: fine-focus sealed tube	6365 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.660, T_max = 0.805	k = −44→44
28196 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0387P)² + 6.6421P] where P = (F_o² + 2F_c²)/3
7506 reflections	(Δ/σ)_max = 0.001
429 parameters	Δρ_max = 1.25 e Å⁻³
8 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

C₁₀H₉N₂⁺·C₈H₃I₃NO₄⁻·C₈H₄I₃NO₄	V = 3321.3 (3) Å³
M_r = 1273.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7388 (4) Å	µ = 5.66 mm⁻¹
b = 34.2377 (19) Å	T = 295 K
c = 13.0739 (7) Å	0.08 × 0.06 × 0.04 mm
β = 106.506 (1)°

Data collection top

Bruker SMART APEX diffractometer	7506 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6365 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.805	R_int = 0.037
28196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	8 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.25 e Å⁻³
7506 reflections	Δρ_min = −1.26 e Å⁻³
429 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.89589 (4)	0.633599 (10)	0.26091 (3)	0.03827 (9)
I2	0.17486 (6)	0.713602 (10)	0.08490 (4)	0.05879 (13)
I3	0.22245 (5)	0.537807 (9)	0.07851 (3)	0.03820 (9)
I4	0.63572 (4)	0.521651 (8)	0.65077 (2)	0.03066 (8)
I5	0.57056 (6)	0.666532 (10)	0.90690 (3)	0.04259 (10)
I6	0.36084 (5)	0.672374 (10)	0.42509 (3)	0.04230 (10)
O1	0.6872 (5)	0.54473 (9)	0.2775 (2)	0.0315 (7)
O2	0.6823 (5)	0.54041 (10)	0.1070 (3)	0.0370 (8)
O3	0.6689 (6)	0.71617 (11)	0.1148 (3)	0.0430 (9)
H3O	0.724 (12)	0.7376 (14)	0.130 (7)	0.12 (4)*
O4	0.6193 (7)	0.72189 (11)	0.2738 (3)	0.0577 (12)
O5	0.6413 (5)	0.58392 (11)	0.4353 (3)	0.0368 (8)
H5O	0.628 (8)	0.5720 (16)	0.377 (3)	0.055 (19)*
O6	0.3505 (5)	0.56703 (11)	0.4066 (3)	0.0432 (9)
O7	0.5332 (5)	0.56640 (12)	0.9082 (3)	0.0394 (8)
H7O	0.575 (9)	0.5570 (19)	0.970 (2)	0.07 (2)*
O8	0.8114 (5)	0.56830 (13)	0.8926 (3)	0.0449 (9)
N1	0.0653 (6)	0.62476 (12)	0.0256 (4)	0.0362 (9)
H11	0.004 (7)	0.6029 (9)	0.018 (4)	0.045 (16)*
H12	−0.001 (7)	0.6455 (11)	0.029 (5)	0.048 (17)*
N2	0.4185 (7)	0.69823 (12)	0.6687 (4)	0.0423 (11)
H21	0.461 (8)	0.7106 (16)	0.730 (3)	0.052 (18)*
H22	0.412 (8)	0.7143 (14)	0.615 (3)	0.048 (17)*
N3	0.8284 (5)	0.47376 (12)	0.3134 (3)	0.0324 (9)
H3	0.787 (8)	0.4976 (7)	0.299 (5)	0.055 (18)*
N4	1.1535 (6)	0.28111 (12)	0.3578 (4)	0.0399 (10)
C1	0.6421 (6)	0.55702 (12)	0.1815 (3)	0.0255 (9)
C2	0.5326 (6)	0.59425 (12)	0.1600 (3)	0.0228 (9)
C3	0.6155 (6)	0.63055 (12)	0.1880 (3)	0.0241 (9)
C4	0.5151 (6)	0.66494 (12)	0.1677 (3)	0.0258 (9)
C5	0.3306 (6)	0.66243 (12)	0.1171 (4)	0.0263 (9)
C6	0.2431 (6)	0.62650 (12)	0.0846 (3)	0.0262 (9)
C7	0.3500 (6)	0.59272 (12)	0.1111 (3)	0.0248 (9)
C8	0.6070 (7)	0.70421 (13)	0.1925 (4)	0.0315 (10)
C9	0.6552 (6)	0.57584 (13)	0.8604 (3)	0.0256 (9)
C10	0.5792 (6)	0.59878 (13)	0.7573 (3)	0.0230 (9)
C11	0.5321 (7)	0.63773 (13)	0.7594 (3)	0.0281 (9)
C12	0.4688 (6)	0.66010 (13)	0.6662 (4)	0.0282 (9)
C13	0.4532 (6)	0.64080 (13)	0.5687 (3)	0.0256 (9)
C14	0.5027 (6)	0.60201 (12)	0.5647 (3)	0.0228 (8)
C15	0.5677 (6)	0.58054 (12)	0.6596 (3)	0.0244 (9)
C16	0.4885 (6)	0.58222 (13)	0.4591 (3)	0.0267 (9)
C17	0.8615 (7)	0.45571 (14)	0.4059 (4)	0.0361 (11)
H17	0.8434	0.4689	0.4641	0.043*
C18	0.9221 (7)	0.41776 (14)	0.4184 (4)	0.0329 (10)
H18	0.9461	0.4056	0.4846	0.040*
C19	0.9471 (6)	0.39770 (12)	0.3306 (4)	0.0258 (9)
C20	0.9103 (7)	0.41793 (14)	0.2341 (4)	0.0337 (11)
H20	0.9257	0.4057	0.1737	0.040*
C21	0.8514 (7)	0.45584 (15)	0.2286 (4)	0.0375 (11)
H21A	0.8271	0.4692	0.1641	0.045*
C22	1.1572 (7)	0.30185 (14)	0.4440 (4)	0.0393 (12)
H22A	1.2063	0.2907	0.5109	0.047*
C23	1.0905 (7)	0.33952 (14)	0.4377 (4)	0.0381 (12)
H23	1.0955	0.3532	0.4999	0.046*
C24	1.0163 (6)	0.35702 (13)	0.3398 (4)	0.0273 (9)
C25	1.0087 (9)	0.33460 (16)	0.2503 (5)	0.0474 (14)
H25	0.9564	0.3446	0.1823	0.057*
C26	1.0804 (9)	0.29694 (16)	0.2632 (5)	0.0505 (15)
H26	1.0766	0.2823	0.2026	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.03160 (17)	0.04546 (19)	0.03463 (18)	−0.00668 (14)	0.00433 (13)	0.00376 (14)
I2	0.0485 (2)	0.02261 (17)	0.1008 (4)	0.00977 (15)	0.0140 (2)	0.00154 (18)
I3	0.0456 (2)	0.02220 (15)	0.03956 (19)	−0.00873 (13)	0.00046 (15)	0.00157 (12)
I4	0.04117 (18)	0.02040 (14)	0.02876 (16)	0.00191 (12)	0.00727 (13)	−0.00067 (11)
I5	0.0665 (2)	0.03696 (18)	0.02578 (17)	0.00401 (16)	0.01550 (16)	−0.00919 (13)
I6	0.0586 (2)	0.03503 (18)	0.02813 (17)	0.00338 (15)	0.00399 (15)	0.00980 (13)
O1	0.048 (2)	0.0260 (16)	0.0220 (16)	0.0110 (14)	0.0115 (14)	0.0039 (12)
O2	0.055 (2)	0.0356 (19)	0.0235 (16)	0.0134 (16)	0.0155 (16)	0.0004 (14)
O3	0.063 (3)	0.034 (2)	0.036 (2)	−0.0227 (18)	0.0215 (18)	−0.0058 (16)
O4	0.106 (4)	0.032 (2)	0.041 (2)	−0.021 (2)	0.031 (2)	−0.0154 (17)
O5	0.048 (2)	0.040 (2)	0.0256 (18)	−0.0024 (16)	0.0162 (16)	−0.0078 (15)
O6	0.047 (2)	0.044 (2)	0.0331 (19)	−0.0068 (17)	0.0031 (17)	−0.0128 (16)
O7	0.0347 (19)	0.054 (2)	0.033 (2)	0.0066 (16)	0.0138 (16)	0.0192 (17)
O8	0.0283 (19)	0.066 (3)	0.037 (2)	0.0010 (17)	0.0044 (15)	0.0109 (18)
N1	0.031 (2)	0.027 (2)	0.044 (2)	−0.0006 (17)	0.0019 (19)	−0.0031 (19)
N2	0.073 (3)	0.020 (2)	0.035 (3)	0.011 (2)	0.017 (2)	0.0015 (18)
N3	0.031 (2)	0.027 (2)	0.040 (2)	0.0103 (17)	0.0100 (18)	0.0067 (17)
N4	0.048 (3)	0.024 (2)	0.052 (3)	0.0102 (18)	0.020 (2)	0.0028 (19)
C1	0.032 (2)	0.0177 (19)	0.026 (2)	−0.0002 (17)	0.0067 (18)	0.0001 (17)
C2	0.035 (2)	0.0186 (19)	0.0145 (19)	0.0001 (17)	0.0065 (17)	0.0022 (15)
C3	0.025 (2)	0.028 (2)	0.020 (2)	−0.0031 (17)	0.0066 (17)	−0.0006 (17)
C4	0.040 (3)	0.0163 (19)	0.023 (2)	−0.0027 (17)	0.0116 (19)	−0.0006 (16)
C5	0.034 (2)	0.0162 (19)	0.030 (2)	0.0028 (17)	0.0112 (19)	0.0021 (17)
C6	0.035 (2)	0.023 (2)	0.022 (2)	0.0023 (18)	0.0102 (18)	0.0008 (17)
C7	0.035 (2)	0.0157 (18)	0.023 (2)	−0.0047 (17)	0.0080 (18)	−0.0014 (16)
C8	0.044 (3)	0.018 (2)	0.033 (2)	−0.0019 (19)	0.011 (2)	−0.0022 (18)
C9	0.033 (3)	0.025 (2)	0.019 (2)	−0.0019 (18)	0.0067 (18)	−0.0033 (16)
C10	0.024 (2)	0.027 (2)	0.018 (2)	−0.0044 (17)	0.0061 (16)	−0.0021 (16)
C11	0.039 (3)	0.025 (2)	0.021 (2)	−0.0028 (19)	0.0092 (19)	−0.0037 (17)
C12	0.034 (3)	0.020 (2)	0.031 (2)	−0.0035 (18)	0.009 (2)	−0.0039 (17)
C13	0.030 (2)	0.027 (2)	0.019 (2)	0.0010 (18)	0.0044 (17)	0.0050 (17)
C14	0.028 (2)	0.0212 (19)	0.021 (2)	−0.0026 (16)	0.0088 (17)	−0.0015 (16)
C15	0.028 (2)	0.020 (2)	0.025 (2)	−0.0013 (16)	0.0073 (18)	−0.0020 (17)
C16	0.034 (3)	0.023 (2)	0.021 (2)	0.0009 (18)	0.0050 (19)	0.0002 (17)
C17	0.041 (3)	0.030 (2)	0.039 (3)	0.011 (2)	0.015 (2)	−0.001 (2)
C18	0.043 (3)	0.026 (2)	0.032 (2)	0.010 (2)	0.015 (2)	0.0045 (19)
C19	0.027 (2)	0.022 (2)	0.029 (2)	0.0044 (17)	0.0088 (18)	0.0023 (17)
C20	0.044 (3)	0.027 (2)	0.033 (3)	0.003 (2)	0.015 (2)	0.0045 (19)
C21	0.046 (3)	0.035 (3)	0.034 (3)	0.007 (2)	0.015 (2)	0.008 (2)
C22	0.049 (3)	0.026 (2)	0.042 (3)	0.008 (2)	0.010 (2)	0.004 (2)
C23	0.050 (3)	0.027 (2)	0.038 (3)	0.007 (2)	0.014 (2)	0.003 (2)
C24	0.026 (2)	0.025 (2)	0.032 (2)	0.0052 (17)	0.0108 (19)	0.0011 (18)
C25	0.064 (4)	0.037 (3)	0.039 (3)	0.015 (3)	0.011 (3)	0.004 (2)
C26	0.078 (4)	0.033 (3)	0.041 (3)	0.016 (3)	0.018 (3)	−0.004 (2)

Geometric parameters (Å, º) top

I1—C3	2.110 (4)	C3—C4	1.394 (6)
I2—C5	2.100 (4)	C4—C5	1.395 (7)
I3—C7	2.110 (4)	C4—C8	1.513 (6)
I4—C15	2.095 (4)	C5—C6	1.410 (6)
I5—C11	2.111 (4)	C6—C7	1.407 (6)
I6—C13	2.108 (4)	C9—C10	1.526 (6)
O1—C1	1.276 (5)	C10—C11	1.385 (6)
O2—C1	1.241 (5)	C10—C15	1.402 (6)
O3—C8	1.307 (6)	C11—C12	1.404 (6)
O3—H3O	0.84 (1)	C12—C13	1.409 (6)
O4—C8	1.203 (6)	C13—C14	1.388 (6)
O5—C16	1.307 (6)	C14—C15	1.406 (6)
O5—H5O	0.84 (1)	C14—C16	1.513 (6)
O6—C16	1.211 (6)	C17—C18	1.375 (6)
O7—C9	1.313 (6)	C17—H17	0.9300
O7—H7O	0.84 (1)	C18—C19	1.398 (6)
O8—C9	1.190 (6)	C18—H18	0.9300
N1—C6	1.374 (6)	C19—C20	1.396 (6)
N1—H11	0.88 (1)	C19—C24	1.485 (6)
N1—H12	0.88 (1)	C20—C21	1.371 (7)
N2—C12	1.366 (6)	C20—H20	0.9300
N2—H21	0.88 (1)	C21—H21A	0.9300
N2—H22	0.88 (1)	C22—C23	1.383 (7)
N3—C17	1.316 (6)	C22—H22A	0.9300
N3—C21	1.323 (7)	C23—C24	1.382 (7)
N3—H3	0.878 (10)	C23—H23	0.9300
N4—C26	1.322 (7)	C24—C25	1.387 (7)
N4—C22	1.325 (7)	C25—C26	1.395 (7)
C1—C2	1.512 (6)	C25—H25	0.9300
C2—C7	1.376 (6)	C26—H26	0.9300
C2—C3	1.399 (6)

C8—O3—H3O	111 (6)	N2—C12—C11	122.2 (4)
C16—O5—H5O	108 (4)	N2—C12—C13	121.2 (4)
C9—O7—H7O	115 (5)	C11—C12—C13	116.6 (4)
C6—N1—H11	122 (4)	C14—C13—C12	122.0 (4)
C6—N1—H12	116 (4)	C14—C13—I6	119.0 (3)
H11—N1—H12	113 (6)	C12—C13—I6	119.0 (3)
C12—N2—H21	117 (4)	C13—C14—C15	120.0 (4)
C12—N2—H22	122 (4)	C13—C14—C16	120.9 (4)
H21—N2—H22	110 (6)	C15—C14—C16	119.1 (4)
C17—N3—C21	121.0 (4)	C10—C15—C14	119.0 (4)
C17—N3—H3	127 (4)	C10—C15—I4	121.8 (3)
C21—N3—H3	112 (4)	C14—C15—I4	119.1 (3)
C26—N4—C22	118.5 (4)	O6—C16—O5	126.6 (4)
O2—C1—O1	124.1 (4)	O6—C16—C14	122.2 (4)
O2—C1—C2	119.6 (4)	O5—C16—C14	111.2 (4)
O1—C1—C2	116.3 (4)	N3—C17—C18	121.6 (5)
C7—C2—C3	119.3 (4)	N3—C17—H17	119.2
C7—C2—C1	120.1 (4)	C18—C17—H17	119.2
C3—C2—C1	120.6 (4)	C17—C18—C19	119.2 (4)
C4—C3—C2	120.7 (4)	C17—C18—H18	120.4
C4—C3—I1	119.4 (3)	C19—C18—H18	120.4
C2—C3—I1	119.9 (3)	C20—C19—C18	117.3 (4)
C3—C4—C5	118.6 (4)	C20—C19—C24	121.0 (4)
C3—C4—C8	120.5 (4)	C18—C19—C24	121.7 (4)
C5—C4—C8	120.8 (4)	C21—C20—C19	119.8 (4)
C4—C5—C6	122.4 (4)	C21—C20—H20	120.1
C4—C5—I2	119.7 (3)	C19—C20—H20	120.1
C6—C5—I2	117.9 (3)	N3—C21—C20	121.1 (5)
N1—C6—C7	121.8 (4)	N3—C21—H21A	119.4
N1—C6—C5	121.7 (4)	C20—C21—H21A	119.4
C7—C6—C5	116.4 (4)	N4—C22—C23	122.1 (5)
C2—C7—C6	122.5 (4)	N4—C22—H22A	119.0
C2—C7—I3	119.2 (3)	C23—C22—H22A	119.0
C6—C7—I3	118.3 (3)	C24—C23—C22	120.6 (5)
O4—C8—O3	125.1 (4)	C24—C23—H23	119.7
O4—C8—C4	123.4 (4)	C22—C23—H23	119.7
O3—C8—C4	111.4 (4)	C23—C24—C25	116.6 (4)
O8—C9—O7	125.0 (4)	C23—C24—C19	121.8 (4)
O8—C9—C10	121.5 (4)	C25—C24—C19	121.5 (4)
O7—C9—C10	113.5 (4)	C24—C25—C26	119.3 (5)
C11—C10—C15	119.9 (4)	C24—C25—H25	120.3
C11—C10—C9	121.0 (4)	C26—C25—H25	120.3
C15—C10—C9	119.0 (4)	N4—C26—C25	122.8 (5)
C10—C11—C12	122.5 (4)	N4—C26—H26	118.6
C10—C11—I5	119.9 (3)	C25—C26—H26	118.6
C12—C11—I5	117.5 (3)

O2—C1—C2—C7	76.5 (6)	C10—C11—C12—C13	0.6 (7)
O1—C1—C2—C7	−103.4 (5)	I5—C11—C12—C13	176.7 (3)
O2—C1—C2—C3	−102.6 (5)	N2—C12—C13—C14	−179.6 (5)
O1—C1—C2—C3	77.5 (5)	C11—C12—C13—C14	−1.9 (7)
C7—C2—C3—C4	0.5 (6)	N2—C12—C13—I6	2.7 (6)
C1—C2—C3—C4	179.6 (4)	C11—C12—C13—I6	−179.6 (3)
C7—C2—C3—I1	−179.1 (3)	C12—C13—C14—C15	1.2 (7)
C1—C2—C3—I1	0.0 (5)	I6—C13—C14—C15	178.9 (3)
C2—C3—C4—C5	−1.2 (6)	C12—C13—C14—C16	−178.6 (4)
I1—C3—C4—C5	178.4 (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—C8	3.0 (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—C6	174.5 (4)	C9—C10—C15—I4	4.2 (6)
C3—C4—C5—I2	−179.9 (3)	C13—C14—C15—C10	0.8 (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—I4	178.6 (3)
I2—C5—C6—N1	5.6 (6)	C16—C14—C15—I4	−1.6 (5)
C4—C5—C6—C7	3.3 (6)	C13—C14—C16—O6	−86.0 (6)
I2—C5—C6—C7	−177.6 (3)	C15—C14—C16—O6	94.1 (6)
C3—C2—C7—C6	2.2 (6)	C13—C14—C16—O5	94.3 (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—C18	0.5 (8)
C1—C2—C7—I3	5.1 (5)	N3—C17—C18—C19	−0.8 (8)
N1—C6—C7—C2	172.8 (4)	C17—C18—C19—C20	0.7 (7)
C5—C6—C7—C2	−4.0 (6)	C17—C18—C19—C24	178.6 (5)
N1—C6—C7—I3	−9.1 (6)	C18—C19—C20—C21	−0.3 (7)
C5—C6—C7—I3	174.0 (3)	C24—C19—C20—C21	−178.2 (5)
C3—C4—C8—O4	−96.2 (6)	C17—N3—C21—C20	0.0 (8)
C5—C4—C8—O4	88.5 (7)	C19—C20—C21—N3	0.0 (8)
C3—C4—C8—O3	84.2 (5)	C26—N4—C22—C23	−1.3 (9)
C5—C4—C8—O3	−91.1 (5)	N4—C22—C23—C24	0.1 (9)
O8—C9—C10—C11	−104.2 (6)	C22—C23—C24—C25	1.6 (8)
O7—C9—C10—C11	74.8 (5)	C22—C23—C24—C19	−178.7 (5)
O8—C9—C10—C15	71.9 (6)	C20—C19—C24—C23	165.6 (5)
O7—C9—C10—C15	−109.2 (5)	C18—C19—C24—C23	−12.2 (7)
C15—C10—C11—C12	1.3 (7)	C20—C19—C24—C25	−14.8 (7)
C9—C10—C11—C12	177.3 (4)	C18—C19—C24—C25	167.4 (5)
C15—C10—C11—I5	−174.7 (3)	C23—C24—C25—C26	−2.2 (9)
C9—C10—C11—I5	1.3 (6)	C19—C24—C25—C26	178.1 (5)
C10—C11—C12—N2	178.4 (5)	C22—N4—C26—C25	0.6 (9)
I5—C11—C12—N2	−5.5 (6)	C24—C25—C26—N4	1.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O8ⁱ	0.88 (1)	2.22 (4)	2.946 (6)	141 (5)
N3—H3···O1	0.88 (1)	1.78 (1)	2.651 (5)	174 (6)
O3—H3o···N4ⁱⁱ	0.84 (1)	1.75 (2)	2.585 (5)	171 (9)
O5—H5o···O1	0.84 (1)	1.77 (3)	2.568 (4)	159 (6)
O7—H7o···O2ⁱⁱⁱ	0.84 (1)	1.84 (1)	2.679 (5)	174 (7)

Symmetry codes: (i) x−1, y, z−1; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₂⁺·C₈H₃I₃NO₄⁻·C₈H₄I₃NO₄
M_r	1273.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.7388 (4), 34.2377 (19), 13.0739 (7)
β (°)	106.506 (1)
V (Å³)	3321.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.66
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.660, 0.805
No. of measured, independent and observed [I > 2σ(I)] reflections	28196, 7506, 6365
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.03
No. of reflections	7506
No. of parameters	429
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.25, −1.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O8ⁱ	0.88 (1)	2.22 (4)	2.946 (6)	141 (5)
N3—H3···O1	0.88 (1)	1.78 (1)	2.651 (5)	174 (6)
O3—H3o···N4ⁱⁱ	0.84 (1)	1.75 (2)	2.585 (5)	171 (9)
O5—H5o···O1	0.84 (1)	1.77 (3)	2.568 (4)	159 (6)
O7—H7o···O2ⁱⁱⁱ	0.84 (1)	1.84 (1)	2.679 (5)	174 (7)

Symmetry codes: (i) x−1, y, z−1; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y, z+1.

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 20773107), Yangzhou University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Beck, T. & Sheldrick, G. M. (2008). Acta Cryst. E64, o1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(4-Pyrid­yl)pyridinium 3-amino-5-carb­­oxy-2,4,6-tri­iodo­benzoate–5-amino-2,4,6-tri­iodo­isophthalic acid (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Pyridyl)pyridinium 3-amino-5-carboxy-2,4,6-triiodobenzoate–5-amino-2,4,6-triiodoisophthalic acid (1/1)