1-{[4′-(1H-1,2,4-Triazol-2-ium-1-ylmeth­yl)biphenyl-4-yl]meth­yl}-1H-1,2,4-triazol-2-ium bis­(3-carb­oxy-5-iodo­benzoate)–5-iodo­benzene-3,5-dicarb­oxy­lic acid–water (1/2/2)

Zhang, K.-L.; Deng, Y.; Ng, S.W.

doi:10.1107/S1600536812014584

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1362

doi:10.1107/S1600536812014584

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1-{[4′-(1H-1,2,4-Triazol-2-ium-1-ylmethyl)biphenyl-4-yl]methyl}-1H-1,2,4-triazol-2-ium bis(3-carboxy-5-iodobenzoate)–5-iodobenzene-3,5-dicarboxylic acid–water (1/2/2)

Kou-Lin Zhang,^a Ye Deng ^a and Seik Weng Ng ^b,^c ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 March 2012; accepted 4 April 2012; online 13 April 2012)

The neutral carboxylic acid molecule and the carboxylate anion in the title compound, C₁₈H₁₈N₆²⁺·2C₈H₄IO₄⁻·2C₈H₅IO₄·2H₂O, are both nearly planar (r.m.s. deviations = 0.034 and 0.045 Å, respectively). In the cation, the mid-point of the C—C bond linking the two benzene rings lies on a center of inversion, and the triazole ring is approximately perpendicular to the adjacent benzene ring [dihedral angle = 83.2 (3)°]. In the crystal, the cations, anions, carboxylic acid and lattice water molecules are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, generating a ribbon running along [1-10]. The crystal studied was a non-merohedral twin with the components in a 51.2 (1):48.8 (1) ratio.

Related literature

For the structure of 5-iodoisophthalic acid, see: Zang et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₈N₆²⁺·2C₈H₄IO₄⁻·2C₈H₅IO₄·2H₂O
M_r = 1520.48
Triclinic, $[P \overline 1]$
a = 8.2620 (9) Å
b = 9.6859 (10) Å
c = 18.661 (2) Å
α = 85.413 (1)°
β = 89.262 (1)°
γ = 65.084 (1)°
V = 1349.7 (2) Å³
Z = 1
Mo Kα radiation
μ = 2.39 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2005 ) T_min = 0.576, T_max = 0.746
17086 measured reflections
6404 independent reflections
4887 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.07
6402 reflections
356 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.84	1.90	2.666 (6)	150
O3—H2⋯N3	0.84	1.84	2.642 (6)	159
O5—H3⋯O8ⁱⁱ	0.84	1.93	2.628 (6)	140
O1w—H5⋯O6ⁱ	0.84	1.97	2.803 (7)	172
O1w—H6⋯O7	0.84	1.81	2.638 (7)	171
N2—H4⋯O1w	0.88	2.12	2.899 (6)	148
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: 10.1107/S1600536812014584/xu5507sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014584/xu5507Isup2.hkl

checkCIF report

Comment top

5-Iodoisophthalic acid furnishes a number of coordination polymers; these feature iodine···π interactions (Zang et al., 2011). Our attempt at synthesizing the cadmium derivative, which was expected to be further connected through 4,4'-bis(1,2,4-triazol-1-ylmethyl)biphenyl, returned instead the salt,(C₁₈H₁₈N₆)²⁺ 2(C₈H₄IO₄)^-.2C₈H₅IO₄^.2H₂O (Scheme I, Fig. 1). The carboxylate ion and the neutral carboxylic acid are both planar (r.m.s.deviation 0.034 and 0.045 Å). The mid-point of the C_phenylene–C_phenylene bond lies on a center-of-inversion. The cation, anion, carboxylic acid and water molecules are linked by N–H···O and O–H···O hydrogen bonds to generate a ribbon running along [1 - 1 0] (Table 1, Fig. 2).

Related literature top

For the structure of 5-iodoisophthalic acid, see: Zang et al. (2011).

Experimental top

A mixture containing cadmium chloride (12.8 mg, 0.1 mmol), 5-iodoisophthalic acid (29.0 mg, 0.1 mmol), 4,4'-bis(1,2,4-triazol-1-ylmethyl)biphenyl (31.6 mg, 0.1 mmol), water (6 ml) and perchloric acid (1 drop) was sealed in a 23 ml, Teflon-lined, stainless-steel Parr bomb. This was heated at 393 K for 3 days. Yellow crystals were isolated from the vessel.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. Thermal ellipsoid plot (Barbour, 2001) of (C₁₈H₁₈N₆)²⁺ 2(C₈H₄IO₄)^-.2C₈H₅IO₄^.2H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The cation lies on a center-of-inversion and symmetry-related atoms are not labeled.
	Fig. 2. Hydrogen-bond ribbon structure.

1-{[4'-(1H-1,2,4-Triazol-2-ium-1-ylmethyl)biphenyl-4-yl]methyl}- 1H-1,2,4-triazol-2-ium bis(3-carboxy-5-iodobenzoate)–5-iodobenzene-3,5-dicarboxylic acid–water (1/2/2) top

Crystal data top

C₁₈H₁₈N₆²⁺·2C₈H₄IO₄⁻·2C₈H₅IO₄·2H₂O	Z = 1
M_r = 1520.48	F(000) = 738
Triclinic, P1	D_x = 1.871 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2620 (9) Å	Cell parameters from 1261 reflections
b = 9.6859 (10) Å	θ = 3.3–23.5°
c = 18.661 (2) Å	µ = 2.39 mm⁻¹
α = 85.413 (1)°	T = 293 K
β = 89.262 (1)°	Prism, yellow
γ = 65.084 (1)°	0.25 × 0.20 × 0.15 mm
V = 1349.7 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	6404 independent reflections
Radiation source: fine-focus sealed tube	4887 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (TWINABS; Bruker, 2005)	h = −10→10
T_min = 0.576, T_max = 0.746	k = −12→12
17086 measured reflections	l = 0→24

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0542P)² + 0.3162P] where P = (F_o² + 2F_c²)/3
6402 reflections	(Δ/σ)_max = 0.001
356 parameters	Δρ_max = 0.51 e Å⁻³
3 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

C₁₈H₁₈N₆²⁺·2C₈H₄IO₄⁻·2C₈H₅IO₄·2H₂O	γ = 65.084 (1)°
M_r = 1520.48	V = 1349.7 (2) Å³
Triclinic, P1	Z = 1
a = 8.2620 (9) Å	Mo Kα radiation
b = 9.6859 (10) Å	µ = 2.39 mm⁻¹
c = 18.661 (2) Å	T = 293 K
α = 85.413 (1)°	0.25 × 0.20 × 0.15 mm
β = 89.262 (1)°

Data collection top

Bruker SMART APEX diffractometer	6404 independent reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2005)	4887 reflections with I > 2σ(I)
T_min = 0.576, T_max = 0.746	R_int = 0.046
17086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	Δρ_max = 0.51 e Å⁻³
6402 reflections	Δρ_min = −1.03 e Å⁻³
356 parameters

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

	x	y	z	U_iso*/U_eq
I1	1.50742 (6)	0.26356 (5)	−0.014572 (19)	0.04613 (13)
I2	−0.01012 (6)	0.73309 (5)	1.025823 (19)	0.04621 (13)
O1	1.7771 (7)	−0.2217 (5)	0.1873 (2)	0.0617 (14)
H1	1.8440	−0.3039	0.2104	0.093*
O2	1.6412 (8)	−0.1715 (6)	0.2909 (3)	0.090 (2)
O3	1.1179 (6)	0.3175 (5)	0.3034 (2)	0.0545 (12)
H2	1.0302	0.3831	0.3230	0.082*
O4	1.0457 (7)	0.5034 (5)	0.2147 (3)	0.0670 (15)
O5	−0.2756 (7)	1.2072 (6)	0.8193 (3)	0.0674 (15)
H3	−0.3436	1.2867	0.7946	0.101*
O6	−0.1152 (7)	1.1631 (5)	0.7186 (2)	0.0629 (15)
O7	0.3845 (7)	0.6420 (6)	0.7091 (3)	0.0642 (14)
O8	0.4582 (7)	0.4805 (6)	0.8062 (3)	0.0673 (15)
O1W	0.6642 (8)	0.4440 (6)	0.6460 (3)	0.0882 (19)
H5	0.7237	0.3629	0.6714	0.132*
H6	0.5784	0.5002	0.6700	0.132*
N1	0.7596 (6)	0.6294 (5)	0.4816 (2)	0.0325 (10)
N2	0.7346 (6)	0.5001 (5)	0.4964 (2)	0.0466 (14)
H4	0.6795	0.4775	0.5330	0.056*
N3	0.8857 (7)	0.4846 (6)	0.3953 (3)	0.0471 (13)
C1	1.6570 (8)	−0.1375 (7)	0.2290 (3)	0.0453 (15)
C2	1.5356 (7)	0.0170 (6)	0.1926 (3)	0.0336 (12)
C3	1.3960 (7)	0.1186 (6)	0.2312 (3)	0.0358 (12)
H2A	1.3745	0.0900	0.2779	0.043*
C4	1.2904 (8)	0.2622 (6)	0.1992 (3)	0.0341 (12)
C5	1.3195 (7)	0.3059 (6)	0.1289 (3)	0.0358 (12)
H5A	1.2481	0.4030	0.1081	0.043*
C6	1.4566 (7)	0.2024 (6)	0.0901 (3)	0.0328 (12)
C7	1.5642 (7)	0.0595 (7)	0.1226 (3)	0.0358 (12)
H7	1.6568	−0.0089	0.0970	0.043*
C8	1.1387 (8)	0.3744 (7)	0.2392 (3)	0.0395 (13)
C9	−0.1449 (8)	1.1247 (7)	0.7801 (3)	0.0407 (14)
C10	−0.0290 (8)	0.9701 (6)	0.8159 (3)	0.0370 (13)
C11	0.1075 (7)	0.8649 (6)	0.7795 (3)	0.0352 (12)
H11	0.1308	0.8900	0.7325	0.042*
C12	0.2110 (7)	0.7203 (6)	0.8133 (3)	0.0338 (12)
C13	0.1764 (7)	0.6829 (6)	0.8832 (3)	0.0352 (12)
H13	0.2443	0.5861	0.9052	0.042*
C14	0.0413 (7)	0.7890 (7)	0.9203 (3)	0.0371 (12)
C15	−0.0623 (7)	0.9314 (7)	0.8872 (3)	0.0369 (12)
H15	−0.1543	1.0022	0.9120	0.044*
C16	0.3617 (8)	0.6048 (6)	0.7742 (3)	0.0390 (13)
C17	0.8114 (8)	0.4178 (7)	0.4436 (4)	0.0462 (15)
H17	0.8149	0.3215	0.4394	0.055*
C18	0.8480 (7)	0.6189 (7)	0.4213 (3)	0.0412 (14)
H18	0.8793	0.6941	0.4001	0.049*
C19	0.6785 (8)	0.7581 (7)	0.5267 (3)	0.0417 (14)
H19A	0.7250	0.8332	0.5137	0.050*
H19B	0.7104	0.7219	0.5768	0.050*
C20	0.4761 (8)	0.8326 (6)	0.5174 (3)	0.0324 (11)
C21	0.3719 (8)	0.8896 (7)	0.5758 (3)	0.0393 (13)
H21	0.4256	0.8836	0.6201	0.047*
C22	0.1836 (7)	0.9571 (7)	0.5684 (3)	0.0379 (13)
H22	0.1152	0.9953	0.6082	0.046*
C23	0.0993 (6)	0.9677 (6)	0.5040 (3)	0.0274 (11)
C24	0.2069 (8)	0.9138 (7)	0.4446 (3)	0.0441 (14)
H24	0.1531	0.9215	0.4000	0.053*
C25	0.3932 (7)	0.8488 (7)	0.4509 (3)	0.0422 (14)
H25	0.4619	0.8162	0.4105	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0417 (2)	0.0500 (3)	0.03632 (19)	−0.01081 (19)	0.00665 (19)	0.00430 (19)
I2	0.0433 (2)	0.0489 (3)	0.03718 (19)	−0.01146 (19)	0.00968 (19)	0.00070 (19)
O1	0.062 (3)	0.036 (3)	0.046 (3)	0.018 (2)	0.005 (2)	0.009 (2)
O2	0.096 (4)	0.060 (3)	0.046 (3)	0.027 (3)	0.019 (3)	0.021 (2)
O3	0.054 (3)	0.046 (3)	0.038 (2)	0.003 (2)	0.010 (2)	−0.005 (2)
O4	0.059 (3)	0.039 (3)	0.058 (3)	0.021 (2)	0.019 (2)	0.001 (2)
O5	0.059 (3)	0.042 (3)	0.060 (3)	0.018 (2)	0.009 (3)	0.003 (2)
O6	0.080 (4)	0.038 (3)	0.036 (3)	0.006 (3)	−0.003 (2)	0.0080 (19)
O7	0.075 (4)	0.052 (3)	0.044 (3)	−0.006 (3)	0.021 (2)	−0.008 (2)
O8	0.061 (3)	0.042 (3)	0.066 (3)	0.010 (2)	0.013 (3)	0.001 (2)
O1W	0.124 (5)	0.056 (3)	0.048 (3)	−0.003 (3)	0.041 (3)	−0.003 (2)
N1	0.028 (2)	0.029 (3)	0.035 (2)	−0.006 (2)	0.0020 (18)	−0.0018 (18)
N2	0.056 (4)	0.035 (3)	0.047 (3)	−0.019 (3)	0.022 (3)	−0.002 (2)
N3	0.040 (3)	0.039 (3)	0.042 (3)	0.003 (2)	0.007 (2)	−0.002 (2)
C1	0.045 (4)	0.037 (3)	0.031 (3)	0.004 (3)	0.005 (3)	0.002 (2)
C2	0.031 (3)	0.025 (3)	0.032 (3)	0.001 (2)	0.002 (2)	−0.004 (2)
C3	0.031 (3)	0.037 (3)	0.031 (3)	−0.006 (3)	0.004 (2)	−0.007 (2)
C4	0.035 (3)	0.029 (3)	0.029 (3)	−0.004 (2)	0.006 (2)	−0.008 (2)
C5	0.037 (3)	0.020 (3)	0.037 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
C6	0.029 (3)	0.032 (3)	0.033 (3)	−0.009 (2)	0.000 (2)	0.002 (2)
C7	0.027 (3)	0.037 (3)	0.034 (3)	−0.004 (2)	0.005 (2)	−0.005 (2)
C8	0.033 (3)	0.035 (3)	0.036 (3)	0.000 (3)	0.001 (2)	−0.008 (2)
C9	0.044 (4)	0.032 (3)	0.034 (3)	−0.003 (3)	−0.004 (2)	−0.005 (2)
C10	0.033 (3)	0.027 (3)	0.035 (3)	0.002 (2)	0.001 (2)	−0.003 (2)
C11	0.028 (3)	0.030 (3)	0.036 (3)	−0.001 (2)	0.002 (2)	−0.002 (2)
C12	0.032 (3)	0.031 (3)	0.032 (3)	−0.006 (2)	0.000 (2)	−0.004 (2)
C13	0.031 (3)	0.026 (3)	0.033 (3)	0.002 (2)	−0.001 (2)	0.003 (2)
C14	0.034 (3)	0.037 (3)	0.034 (3)	−0.008 (3)	0.004 (2)	−0.003 (2)
C15	0.028 (3)	0.035 (3)	0.041 (3)	−0.005 (2)	0.006 (2)	−0.010 (2)
C16	0.037 (3)	0.023 (3)	0.042 (3)	0.002 (3)	0.004 (2)	−0.004 (2)
C17	0.047 (4)	0.025 (3)	0.055 (4)	−0.004 (3)	0.009 (3)	−0.006 (3)
C18	0.038 (3)	0.042 (4)	0.041 (3)	−0.015 (3)	0.009 (2)	0.001 (3)
C19	0.036 (3)	0.041 (4)	0.045 (3)	−0.011 (3)	0.006 (3)	−0.012 (3)
C20	0.031 (3)	0.027 (3)	0.036 (2)	−0.010 (2)	0.005 (3)	−0.007 (2)
C21	0.039 (3)	0.051 (4)	0.030 (3)	−0.020 (3)	0.001 (2)	−0.005 (2)
C22	0.033 (3)	0.048 (4)	0.031 (3)	−0.015 (3)	0.009 (2)	−0.004 (2)
C23	0.027 (3)	0.021 (3)	0.028 (2)	−0.004 (2)	0.002 (2)	0.0001 (19)
C24	0.041 (4)	0.057 (4)	0.027 (3)	−0.013 (3)	−0.004 (2)	−0.006 (3)
C25	0.032 (3)	0.049 (4)	0.035 (3)	−0.005 (3)	0.006 (2)	−0.011 (3)

Geometric parameters (Å, º) top

I1—C6	2.085 (5)	C5—H5A	0.9300
I2—C14	2.086 (5)	C6—C7	1.384 (7)
O1—C1	1.287 (7)	C7—H7	0.9300
O1—H1	0.8400	C9—C10	1.502 (8)
O2—C1	1.195 (8)	C10—C11	1.376 (8)
O3—C8	1.318 (7)	C10—C15	1.408 (7)
O3—H2	0.8400	C11—C12	1.398 (7)
O4—C8	1.212 (7)	C11—H11	0.9300
O5—C9	1.298 (7)	C12—C13	1.385 (7)
O5—H3	0.8400	C12—C16	1.506 (8)
O6—C9	1.232 (7)	C13—C14	1.382 (7)
O7—C16	1.273 (7)	C13—H13	0.9300
O8—C16	1.237 (7)	C14—C15	1.378 (8)
O1W—H5	0.8400	C15—H15	0.9300
O1W—H6	0.8400	C17—H17	0.9300
N1—C18	1.321 (6)	C18—H18	0.9300
N1—N2	1.359 (6)	C19—C20	1.523 (8)
N1—C19	1.469 (7)	C19—H19A	0.9700
N2—C17	1.302 (7)	C19—H19B	0.9700
N2—H4	0.8800	C20—C21	1.380 (7)
N3—C18	1.335 (8)	C20—C25	1.391 (7)
N3—C17	1.355 (7)	C21—C22	1.414 (7)
C1—C2	1.515 (8)	C21—H21	0.9300
C2—C7	1.387 (7)	C22—C23	1.371 (7)
C2—C3	1.397 (7)	C22—H22	0.9300
C3—C4	1.382 (8)	C23—C24	1.404 (7)
C3—H2A	0.9300	C23—C23ⁱ	1.495 (10)
C4—C5	1.395 (7)	C24—C25	1.399 (7)
C4—C8	1.505 (7)	C24—H24	0.9300
C5—C6	1.397 (7)	C25—H25	0.9300

C1—O1—H1	109.5	C13—C12—C16	119.6 (5)
C8—O3—H2	109.5	C11—C12—C16	120.3 (5)
C9—O5—H3	109.5	C14—C13—C12	120.3 (5)
H5—O1W—H6	108.6	C14—C13—H13	119.9
C18—N1—N2	109.3 (5)	C12—C13—H13	119.9
C18—N1—C19	130.2 (5)	C15—C14—C13	120.0 (5)
N2—N1—C19	120.3 (4)	C15—C14—I2	119.7 (4)
C17—N2—N1	103.6 (4)	C13—C14—I2	120.3 (4)
C17—N2—H4	128.2	C14—C15—C10	120.1 (5)
N1—N2—H4	128.2	C14—C15—H15	119.9
C18—N3—C17	102.9 (5)	C10—C15—H15	119.9
O2—C1—O1	125.4 (6)	O8—C16—O7	123.1 (5)
O2—C1—C2	121.5 (6)	O8—C16—C12	119.4 (5)
O1—C1—C2	113.1 (5)	O7—C16—C12	117.5 (5)
C7—C2—C3	120.0 (5)	N2—C17—N3	114.1 (5)
C7—C2—C1	120.9 (5)	N2—C17—H17	123.0
C3—C2—C1	119.2 (5)	N3—C17—H17	123.0
C4—C3—C2	119.2 (5)	N1—C18—N3	110.1 (5)
C4—C3—H2A	120.4	N1—C18—H18	125.0
C2—C3—H2A	120.4	N3—C18—H18	125.0
C3—C4—C5	121.0 (5)	N1—C19—C20	111.1 (5)
C3—C4—C8	120.6 (5)	N1—C19—H19A	109.4
C5—C4—C8	118.4 (5)	C20—C19—H19A	109.4
C4—C5—C6	119.4 (5)	N1—C19—H19B	109.4
C4—C5—H5A	120.3	C20—C19—H19B	109.4
C6—C5—H5A	120.3	H19A—C19—H19B	108.0
C7—C6—C5	119.5 (5)	C21—C20—C25	119.0 (5)
C7—C6—I1	119.6 (4)	C21—C20—C19	119.4 (5)
C5—C6—I1	120.8 (4)	C25—C20—C19	121.6 (5)
C6—C7—C2	120.8 (5)	C20—C21—C22	120.2 (5)
C6—C7—H7	119.6	C20—C21—H21	119.9
C2—C7—H7	119.6	C22—C21—H21	119.9
O4—C8—O3	123.7 (5)	C23—C22—C21	121.7 (5)
O4—C8—C4	123.4 (5)	C23—C22—H22	119.2
O3—C8—C4	112.9 (5)	C21—C22—H22	119.2
O6—C9—O5	125.4 (6)	C22—C23—C24	117.5 (5)
O6—C9—C10	120.9 (5)	C22—C23—C23ⁱ	122.4 (6)
O5—C9—C10	113.7 (5)	C24—C23—C23ⁱ	120.0 (6)
C11—C10—C15	119.7 (5)	C25—C24—C23	121.4 (5)
C11—C10—C9	120.7 (5)	C25—C24—H24	119.3
C15—C10—C9	119.6 (5)	C23—C24—H24	119.3
C10—C11—C12	119.8 (5)	C20—C25—C24	120.1 (5)
C10—C11—H11	120.1	C20—C25—H25	119.9
C12—C11—H11	120.1	C24—C25—H25	119.9
C13—C12—C11	120.1 (5)

C18—N1—N2—C17	0.4 (6)	C16—C12—C13—C14	178.4 (5)
C19—N1—N2—C17	175.2 (5)	C12—C13—C14—C15	1.5 (9)
O2—C1—C2—C7	174.9 (7)	C12—C13—C14—I2	−179.7 (4)
O1—C1—C2—C7	−3.3 (9)	C13—C14—C15—C10	−1.0 (9)
O2—C1—C2—C3	−3.5 (10)	I2—C14—C15—C10	−179.8 (4)
O1—C1—C2—C3	178.3 (6)	C11—C10—C15—C14	−0.1 (9)
C7—C2—C3—C4	−1.4 (9)	C9—C10—C15—C14	178.9 (5)
C1—C2—C3—C4	177.0 (6)	C13—C12—C16—O8	−3.4 (9)
C2—C3—C4—C5	1.0 (9)	C11—C12—C16—O8	176.0 (6)
C2—C3—C4—C8	179.9 (5)	C13—C12—C16—O7	177.5 (6)
C3—C4—C5—C6	0.5 (9)	C11—C12—C16—O7	−3.1 (9)
C8—C4—C5—C6	−178.5 (5)	N1—N2—C17—N3	0.2 (7)
C4—C5—C6—C7	−1.5 (8)	C18—N3—C17—N2	−0.7 (7)
C4—C5—C6—I1	−179.1 (4)	N2—N1—C18—N3	−0.8 (7)
C5—C6—C7—C2	1.1 (9)	C19—N1—C18—N3	−174.9 (5)
I1—C6—C7—C2	178.7 (4)	C17—N3—C18—N1	0.9 (7)
C3—C2—C7—C6	0.4 (9)	C18—N1—C19—C20	105.3 (6)
C1—C2—C7—C6	−178.0 (5)	N2—N1—C19—C20	−68.3 (6)
C3—C4—C8—O4	177.5 (6)	N1—C19—C20—C21	144.5 (5)
C5—C4—C8—O4	−3.6 (10)	N1—C19—C20—C25	−37.4 (7)
C3—C4—C8—O3	−2.6 (8)	C25—C20—C21—C22	2.8 (9)
C5—C4—C8—O3	176.3 (6)	C19—C20—C21—C22	−179.0 (5)
O6—C9—C10—C11	−3.3 (10)	C20—C21—C22—C23	0.2 (9)
O5—C9—C10—C11	175.3 (6)	C21—C22—C23—C24	−2.2 (8)
O6—C9—C10—C15	177.7 (6)	C21—C22—C23—C23ⁱ	177.2 (6)
O5—C9—C10—C15	−3.6 (9)	C22—C23—C24—C25	1.3 (9)
C15—C10—C11—C12	0.6 (9)	C23ⁱ—C23—C24—C25	−178.2 (6)
C9—C10—C11—C12	−178.4 (5)	C21—C20—C25—C24	−3.7 (9)
C10—C11—C12—C13	−0.1 (9)	C19—C20—C25—C24	178.1 (6)
C10—C11—C12—C16	−179.5 (5)	C23—C24—C25—C20	1.7 (9)
C11—C12—C13—C14	−1.0 (9)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱⁱ	0.84	1.90	2.666 (6)	150
O3—H2···N3	0.84	1.84	2.642 (6)	159
O5—H3···O8ⁱⁱⁱ	0.84	1.93	2.628 (6)	140
O1w—H5···O6ⁱⁱ	0.84	1.97	2.803 (7)	172
O1w—H6···O7	0.84	1.81	2.638 (7)	171
N2—H4···O1w	0.88	2.12	2.899 (6)	148

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₆²⁺·2C₈H₄IO₄⁻·2C₈H₅IO₄·2H₂O
M_r	1520.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2620 (9), 9.6859 (10), 18.661 (2)
α, β, γ (°)	85.413 (1), 89.262 (1), 65.084 (1)
V (Å³)	1349.7 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.39
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (TWINABS; Bruker, 2005)
T_min, T_max	0.576, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	17086, 6404, 4887
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.07
No. of reflections	6402
No. of parameters	356
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −1.03

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O1—H1···O4ⁱ	0.84	1.90	2.666 (6)	150
O3—H2···N3	0.84	1.84	2.642 (6)	159
O5—H3···O8ⁱⁱ	0.84	1.93	2.628 (6)	140
O1w—H5···O6ⁱ	0.84	1.97	2.803 (7)	172
O1w—H6···O7	0.84	1.81	2.638 (7)	171
N2—H4···O1w	0.88	2.12	2.899 (6)	148

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

Acknowledgements

This study is a project funded by the Priority Academic Development Program of Jiangsu Higher Education Institution (PAPD). We also thank the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2, SAINT and TWINABS. Bruker AXS, Madison, Wisconsin, USA. 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
Zang, S.-Q., Fan, Y.-J., Li, J.-B., Hou, H.-W. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 3395–3405. Web of Science CSD CrossRef CAS Google Scholar

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Volume 68| Part 5| May 2012| Page o1362

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

1-{[4′-(1H-1,2,4-Triazol-2-ium-1-ylmeth­yl)bi­phenyl-4-yl]meth­yl}-1H-1,2,4-triazol-2-ium bis­­(3-carb­­oxy-5-iodo­benzoate)–5-iodo­benzene-3,5-dicarb­­oxy­lic acid–water (1/2/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{[4′-(1H-1,2,4-Triazol-2-ium-1-ylmethyl)biphenyl-4-yl]methyl}-1H-1,2,4-triazol-2-ium bis(3-carboxy-5-iodobenzoate)–5-iodobenzene-3,5-dicarboxylic acid–water (1/2/2)