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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1362

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)

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[Zang, S.-Q., Fan, Y.-J., Li, J.-B., Hou, H.-W. & Mak, T. C. W. (2011). Cryst. Growth Des. 11, 3395-3405.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N62+·2C8H4IO4·2C8H5IO4·2H2O

  • Mr = 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[Bruker (2005). APEX2, SAINT and TWINABS. Bruker AXS, Madison, Wisconsin, USA.]) Tmin = 0.576, Tmax = 0.746

  • 17086 measured reflections

  • 6404 independent reflections

  • 4887 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.51 e Å−3

  • Δρmin = −1.03 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2, SAINT and TWINABS. Bruker AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and TWINABS. Bruker AXS, Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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 Cphenylene–Cphenylene 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

For the carboxyl groups, an acid hydrogen was placed on the oxygen atom with long C–O bonds, i.e., ca. 1.30 Å in the riding mode. One carboxylic entity has one such long bonds whereas the other has two; in the latter case, the entity was assumed to be a neutral carboxylic acid molecule. The water hydrogen atoms were placed in chemically sensible positions on the basis of hydrogen-bonding interactions; the O–H distance was set to 0.84 Å, and the temperature factors were set to 1.5 times that of the parent atom. In this scheme of hydrogen atoms, the nitrogen atom at the 2-position of the triazole should be protonated; this was treated as riding [N–H = 0.88 Å, U(H) = 1.2U(N)].

The final difference Fourier map had a peak at 0.73 Å from I1.

Omitted owing to bad disagreement were (6 4 4), (8 3 7), (-4 - 5 2), (5 4 0), (-3 - 2 14), (-2 8 0), (1 - 2 3), (2 1 1), (-6 - 4 3), (9 3 7), (7 4 4),(-1 8 0), (-2 - 1 1), (8 4 8), (-7 4 7), (-4 - 6 3), (-3 - 6 3), (-6 4 7), (-5 4 7) and (8 3 10). The large number of omissions is an artifact of twinning. The crystal is a non-merohedral twin with the components being in a 51.2 (1): 48.8 ratio.

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
[Figure 1] 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.
[Figure 2] 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+·2C8H4IO4·2C8H5IO4·2H2OZ = 1
Mr = 1520.48F(000) = 738
Triclinic, P1Dx = 1.871 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2620 (9) ÅCell parameters from 1261 reflections
b = 9.6859 (10) Åθ = 3.3–23.5°
c = 18.661 (2) ŵ = 2.39 mm1
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 tube4887 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(TWINABS; Bruker, 2005)
h = 1010
Tmin = 0.576, Tmax = 0.746k = 1212
17086 measured reflectionsl = 024
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3162P]
where P = (Fo2 + 2Fc2)/3
6402 reflections(Δ/σ)max = 0.001
356 parametersΔρmax = 0.51 e Å3
3 restraintsΔρmin = 1.03 e Å3
Crystal data top
C18H18N62+·2C8H4IO4·2C8H5IO4·2H2Oγ = 65.084 (1)°
Mr = 1520.48V = 1349.7 (2) Å3
Triclinic, P1Z = 1
a = 8.2620 (9) ÅMo Kα radiation
b = 9.6859 (10) ŵ = 2.39 mm1
c = 18.661 (2) ÅT = 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)
Tmin = 0.576, Tmax = 0.746Rint = 0.046
17086 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0413 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.07Δρmax = 0.51 e Å3
6402 reflectionsΔρmin = 1.03 e Å3
356 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.50742 (6)0.26356 (5)0.014572 (19)0.04613 (13)
I20.01012 (6)0.73309 (5)1.025823 (19)0.04621 (13)
O11.7771 (7)0.2217 (5)0.1873 (2)0.0617 (14)
H11.84400.30390.21040.093*
O21.6412 (8)0.1715 (6)0.2909 (3)0.090 (2)
O31.1179 (6)0.3175 (5)0.3034 (2)0.0545 (12)
H21.03020.38310.32300.082*
O41.0457 (7)0.5034 (5)0.2147 (3)0.0670 (15)
O50.2756 (7)1.2072 (6)0.8193 (3)0.0674 (15)
H30.34361.28670.79460.101*
O60.1152 (7)1.1631 (5)0.7186 (2)0.0629 (15)
O70.3845 (7)0.6420 (6)0.7091 (3)0.0642 (14)
O80.4582 (7)0.4805 (6)0.8062 (3)0.0673 (15)
O1W0.6642 (8)0.4440 (6)0.6460 (3)0.0882 (19)
H50.72370.36290.67140.132*
H60.57840.50020.67000.132*
N10.7596 (6)0.6294 (5)0.4816 (2)0.0325 (10)
N20.7346 (6)0.5001 (5)0.4964 (2)0.0466 (14)
H40.67950.47750.53300.056*
N30.8857 (7)0.4846 (6)0.3953 (3)0.0471 (13)
C11.6570 (8)0.1375 (7)0.2290 (3)0.0453 (15)
C21.5356 (7)0.0170 (6)0.1926 (3)0.0336 (12)
C31.3960 (7)0.1186 (6)0.2312 (3)0.0358 (12)
H2A1.37450.09000.27790.043*
C41.2904 (8)0.2622 (6)0.1992 (3)0.0341 (12)
C51.3195 (7)0.3059 (6)0.1289 (3)0.0358 (12)
H5A1.24810.40300.10810.043*
C61.4566 (7)0.2024 (6)0.0901 (3)0.0328 (12)
C71.5642 (7)0.0595 (7)0.1226 (3)0.0358 (12)
H71.65680.00890.09700.043*
C81.1387 (8)0.3744 (7)0.2392 (3)0.0395 (13)
C90.1449 (8)1.1247 (7)0.7801 (3)0.0407 (14)
C100.0290 (8)0.9701 (6)0.8159 (3)0.0370 (13)
C110.1075 (7)0.8649 (6)0.7795 (3)0.0352 (12)
H110.13080.89000.73250.042*
C120.2110 (7)0.7203 (6)0.8133 (3)0.0338 (12)
C130.1764 (7)0.6829 (6)0.8832 (3)0.0352 (12)
H130.24430.58610.90520.042*
C140.0413 (7)0.7890 (7)0.9203 (3)0.0371 (12)
C150.0623 (7)0.9314 (7)0.8872 (3)0.0369 (12)
H150.15431.00220.91200.044*
C160.3617 (8)0.6048 (6)0.7742 (3)0.0390 (13)
C170.8114 (8)0.4178 (7)0.4436 (4)0.0462 (15)
H170.81490.32150.43940.055*
C180.8480 (7)0.6189 (7)0.4213 (3)0.0412 (14)
H180.87930.69410.40010.049*
C190.6785 (8)0.7581 (7)0.5267 (3)0.0417 (14)
H19A0.72500.83320.51370.050*
H19B0.71040.72190.57680.050*
C200.4761 (8)0.8326 (6)0.5174 (3)0.0324 (11)
C210.3719 (8)0.8896 (7)0.5758 (3)0.0393 (13)
H210.42560.88360.62010.047*
C220.1836 (7)0.9571 (7)0.5684 (3)0.0379 (13)
H220.11520.99530.60820.046*
C230.0993 (6)0.9677 (6)0.5040 (3)0.0274 (11)
C240.2069 (8)0.9138 (7)0.4446 (3)0.0441 (14)
H240.15310.92150.40000.053*
C250.3932 (7)0.8488 (7)0.4509 (3)0.0422 (14)
H250.46190.81620.41050.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0417 (2)0.0500 (3)0.03632 (19)0.01081 (19)0.00665 (19)0.00430 (19)
I20.0433 (2)0.0489 (3)0.03718 (19)0.01146 (19)0.00968 (19)0.00070 (19)
O10.062 (3)0.036 (3)0.046 (3)0.018 (2)0.005 (2)0.009 (2)
O20.096 (4)0.060 (3)0.046 (3)0.027 (3)0.019 (3)0.021 (2)
O30.054 (3)0.046 (3)0.038 (2)0.003 (2)0.010 (2)0.005 (2)
O40.059 (3)0.039 (3)0.058 (3)0.021 (2)0.019 (2)0.001 (2)
O50.059 (3)0.042 (3)0.060 (3)0.018 (2)0.009 (3)0.003 (2)
O60.080 (4)0.038 (3)0.036 (3)0.006 (3)0.003 (2)0.0080 (19)
O70.075 (4)0.052 (3)0.044 (3)0.006 (3)0.021 (2)0.008 (2)
O80.061 (3)0.042 (3)0.066 (3)0.010 (2)0.013 (3)0.001 (2)
O1W0.124 (5)0.056 (3)0.048 (3)0.003 (3)0.041 (3)0.003 (2)
N10.028 (2)0.029 (3)0.035 (2)0.006 (2)0.0020 (18)0.0018 (18)
N20.056 (4)0.035 (3)0.047 (3)0.019 (3)0.022 (3)0.002 (2)
N30.040 (3)0.039 (3)0.042 (3)0.003 (2)0.007 (2)0.002 (2)
C10.045 (4)0.037 (3)0.031 (3)0.004 (3)0.005 (3)0.002 (2)
C20.031 (3)0.025 (3)0.032 (3)0.001 (2)0.002 (2)0.004 (2)
C30.031 (3)0.037 (3)0.031 (3)0.006 (3)0.004 (2)0.007 (2)
C40.035 (3)0.029 (3)0.029 (3)0.004 (2)0.006 (2)0.008 (2)
C50.037 (3)0.020 (3)0.037 (3)0.001 (2)0.000 (2)0.000 (2)
C60.029 (3)0.032 (3)0.033 (3)0.009 (2)0.000 (2)0.002 (2)
C70.027 (3)0.037 (3)0.034 (3)0.004 (2)0.005 (2)0.005 (2)
C80.033 (3)0.035 (3)0.036 (3)0.000 (3)0.001 (2)0.008 (2)
C90.044 (4)0.032 (3)0.034 (3)0.003 (3)0.004 (2)0.005 (2)
C100.033 (3)0.027 (3)0.035 (3)0.002 (2)0.001 (2)0.003 (2)
C110.028 (3)0.030 (3)0.036 (3)0.001 (2)0.002 (2)0.002 (2)
C120.032 (3)0.031 (3)0.032 (3)0.006 (2)0.000 (2)0.004 (2)
C130.031 (3)0.026 (3)0.033 (3)0.002 (2)0.001 (2)0.003 (2)
C140.034 (3)0.037 (3)0.034 (3)0.008 (3)0.004 (2)0.003 (2)
C150.028 (3)0.035 (3)0.041 (3)0.005 (2)0.006 (2)0.010 (2)
C160.037 (3)0.023 (3)0.042 (3)0.002 (3)0.004 (2)0.004 (2)
C170.047 (4)0.025 (3)0.055 (4)0.004 (3)0.009 (3)0.006 (3)
C180.038 (3)0.042 (4)0.041 (3)0.015 (3)0.009 (2)0.001 (3)
C190.036 (3)0.041 (4)0.045 (3)0.011 (3)0.006 (3)0.012 (3)
C200.031 (3)0.027 (3)0.036 (2)0.010 (2)0.005 (3)0.007 (2)
C210.039 (3)0.051 (4)0.030 (3)0.020 (3)0.001 (2)0.005 (2)
C220.033 (3)0.048 (4)0.031 (3)0.015 (3)0.009 (2)0.004 (2)
C230.027 (3)0.021 (3)0.028 (2)0.004 (2)0.002 (2)0.0001 (19)
C240.041 (4)0.057 (4)0.027 (3)0.013 (3)0.004 (2)0.006 (3)
C250.032 (3)0.049 (4)0.035 (3)0.005 (3)0.006 (2)0.011 (3)
Geometric parameters (Å, º) top
I1—C62.085 (5)C5—H5A0.9300
I2—C142.086 (5)C6—C71.384 (7)
O1—C11.287 (7)C7—H70.9300
O1—H10.8400C9—C101.502 (8)
O2—C11.195 (8)C10—C111.376 (8)
O3—C81.318 (7)C10—C151.408 (7)
O3—H20.8400C11—C121.398 (7)
O4—C81.212 (7)C11—H110.9300
O5—C91.298 (7)C12—C131.385 (7)
O5—H30.8400C12—C161.506 (8)
O6—C91.232 (7)C13—C141.382 (7)
O7—C161.273 (7)C13—H130.9300
O8—C161.237 (7)C14—C151.378 (8)
O1W—H50.8400C15—H150.9300
O1W—H60.8400C17—H170.9300
N1—C181.321 (6)C18—H180.9300
N1—N21.359 (6)C19—C201.523 (8)
N1—C191.469 (7)C19—H19A0.9700
N2—C171.302 (7)C19—H19B0.9700
N2—H40.8800C20—C211.380 (7)
N3—C181.335 (8)C20—C251.391 (7)
N3—C171.355 (7)C21—C221.414 (7)
C1—C21.515 (8)C21—H210.9300
C2—C71.387 (7)C22—C231.371 (7)
C2—C31.397 (7)C22—H220.9300
C3—C41.382 (8)C23—C241.404 (7)
C3—H2A0.9300C23—C23i1.495 (10)
C4—C51.395 (7)C24—C251.399 (7)
C4—C81.505 (7)C24—H240.9300
C5—C61.397 (7)C25—H250.9300
C1—O1—H1109.5C13—C12—C16119.6 (5)
C8—O3—H2109.5C11—C12—C16120.3 (5)
C9—O5—H3109.5C14—C13—C12120.3 (5)
H5—O1W—H6108.6C14—C13—H13119.9
C18—N1—N2109.3 (5)C12—C13—H13119.9
C18—N1—C19130.2 (5)C15—C14—C13120.0 (5)
N2—N1—C19120.3 (4)C15—C14—I2119.7 (4)
C17—N2—N1103.6 (4)C13—C14—I2120.3 (4)
C17—N2—H4128.2C14—C15—C10120.1 (5)
N1—N2—H4128.2C14—C15—H15119.9
C18—N3—C17102.9 (5)C10—C15—H15119.9
O2—C1—O1125.4 (6)O8—C16—O7123.1 (5)
O2—C1—C2121.5 (6)O8—C16—C12119.4 (5)
O1—C1—C2113.1 (5)O7—C16—C12117.5 (5)
C7—C2—C3120.0 (5)N2—C17—N3114.1 (5)
C7—C2—C1120.9 (5)N2—C17—H17123.0
C3—C2—C1119.2 (5)N3—C17—H17123.0
C4—C3—C2119.2 (5)N1—C18—N3110.1 (5)
C4—C3—H2A120.4N1—C18—H18125.0
C2—C3—H2A120.4N3—C18—H18125.0
C3—C4—C5121.0 (5)N1—C19—C20111.1 (5)
C3—C4—C8120.6 (5)N1—C19—H19A109.4
C5—C4—C8118.4 (5)C20—C19—H19A109.4
C4—C5—C6119.4 (5)N1—C19—H19B109.4
C4—C5—H5A120.3C20—C19—H19B109.4
C6—C5—H5A120.3H19A—C19—H19B108.0
C7—C6—C5119.5 (5)C21—C20—C25119.0 (5)
C7—C6—I1119.6 (4)C21—C20—C19119.4 (5)
C5—C6—I1120.8 (4)C25—C20—C19121.6 (5)
C6—C7—C2120.8 (5)C20—C21—C22120.2 (5)
C6—C7—H7119.6C20—C21—H21119.9
C2—C7—H7119.6C22—C21—H21119.9
O4—C8—O3123.7 (5)C23—C22—C21121.7 (5)
O4—C8—C4123.4 (5)C23—C22—H22119.2
O3—C8—C4112.9 (5)C21—C22—H22119.2
O6—C9—O5125.4 (6)C22—C23—C24117.5 (5)
O6—C9—C10120.9 (5)C22—C23—C23i122.4 (6)
O5—C9—C10113.7 (5)C24—C23—C23i120.0 (6)
C11—C10—C15119.7 (5)C25—C24—C23121.4 (5)
C11—C10—C9120.7 (5)C25—C24—H24119.3
C15—C10—C9119.6 (5)C23—C24—H24119.3
C10—C11—C12119.8 (5)C20—C25—C24120.1 (5)
C10—C11—H11120.1C20—C25—H25119.9
C12—C11—H11120.1C24—C25—H25119.9
C13—C12—C11120.1 (5)
C18—N1—N2—C170.4 (6)C16—C12—C13—C14178.4 (5)
C19—N1—N2—C17175.2 (5)C12—C13—C14—C151.5 (9)
O2—C1—C2—C7174.9 (7)C12—C13—C14—I2179.7 (4)
O1—C1—C2—C73.3 (9)C13—C14—C15—C101.0 (9)
O2—C1—C2—C33.5 (10)I2—C14—C15—C10179.8 (4)
O1—C1—C2—C3178.3 (6)C11—C10—C15—C140.1 (9)
C7—C2—C3—C41.4 (9)C9—C10—C15—C14178.9 (5)
C1—C2—C3—C4177.0 (6)C13—C12—C16—O83.4 (9)
C2—C3—C4—C51.0 (9)C11—C12—C16—O8176.0 (6)
C2—C3—C4—C8179.9 (5)C13—C12—C16—O7177.5 (6)
C3—C4—C5—C60.5 (9)C11—C12—C16—O73.1 (9)
C8—C4—C5—C6178.5 (5)N1—N2—C17—N30.2 (7)
C4—C5—C6—C71.5 (8)C18—N3—C17—N20.7 (7)
C4—C5—C6—I1179.1 (4)N2—N1—C18—N30.8 (7)
C5—C6—C7—C21.1 (9)C19—N1—C18—N3174.9 (5)
I1—C6—C7—C2178.7 (4)C17—N3—C18—N10.9 (7)
C3—C2—C7—C60.4 (9)C18—N1—C19—C20105.3 (6)
C1—C2—C7—C6178.0 (5)N2—N1—C19—C2068.3 (6)
C3—C4—C8—O4177.5 (6)N1—C19—C20—C21144.5 (5)
C5—C4—C8—O43.6 (10)N1—C19—C20—C2537.4 (7)
C3—C4—C8—O32.6 (8)C25—C20—C21—C222.8 (9)
C5—C4—C8—O3176.3 (6)C19—C20—C21—C22179.0 (5)
O6—C9—C10—C113.3 (10)C20—C21—C22—C230.2 (9)
O5—C9—C10—C11175.3 (6)C21—C22—C23—C242.2 (8)
O6—C9—C10—C15177.7 (6)C21—C22—C23—C23i177.2 (6)
O5—C9—C10—C153.6 (9)C22—C23—C24—C251.3 (9)
C15—C10—C11—C120.6 (9)C23i—C23—C24—C25178.2 (6)
C9—C10—C11—C12178.4 (5)C21—C20—C25—C243.7 (9)
C10—C11—C12—C130.1 (9)C19—C20—C25—C24178.1 (6)
C10—C11—C12—C16179.5 (5)C23—C24—C25—C201.7 (9)
C11—C12—C13—C141.0 (9)
Symmetry code: (i) x, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4ii0.841.902.666 (6)150
O3—H2···N30.841.842.642 (6)159
O5—H3···O8iii0.841.932.628 (6)140
O1w—H5···O6ii0.841.972.803 (7)172
O1w—H6···O70.841.812.638 (7)171
N2—H4···O1w0.882.122.899 (6)148
Symmetry codes: (ii) x+1, y1, z; (iii) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC18H18N62+·2C8H4IO4·2C8H5IO4·2H2O
Mr1520.48
Crystal system, space groupTriclinic, 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)
V3)1349.7 (2)
Z1
Radiation typeMo Kα
µ (mm1)2.39
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(TWINABS; Bruker, 2005)
Tmin, Tmax0.576, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
17086, 6404, 4887
Rint0.046
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.116, 1.07
No. of reflections6402
No. of parameters356
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O4i0.841.902.666 (6)150
O3—H2···N30.841.842.642 (6)159
O5—H3···O8ii0.841.932.628 (6)140
O1w—H5···O6i0.841.972.803 (7)172
O1w—H6···O70.841.812.638 (7)171
N2—H4···O1w0.882.122.899 (6)148
Symmetry codes: (i) x+1, y1, z; (ii) x1, 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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2, SAINT and TWINABS. Bruker AXS, Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZang, 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Volume 68| Part 5| May 2012| Page o1362
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