1,1′-(Ethane-1,2-di­yl)dipyridinium bis­(iodate)

Gholizadeh, M.; Maleki, B.; Pourayoubi, M.; Kia, M.; Notash, B.

doi:10.1107/S1600536811020927

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1614-o1615

doi:10.1107/S1600536811020927

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1,1′-(Ethane-1,2-diyl)dipyridinium bis(iodate)

Mostafa Gholizadeh,^a ^* Behrooz Maleki,^b Mehrdad Pourayoubi,^a Mehdi Kia ^b and Behrouz Notash ^c

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, ^bDepartment of Chemistry, Sabzevar Tarbiat Moallem University, Sabzevar, Iran, and ^cChemistry Department, Shahid Beheshti University, G. C. Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: mostafa_gholizadeh@yahoo.com

(Received 16 May 2011; accepted 31 May 2011; online 11 June 2011)

The title salt, C₁₂H₁₄N₂²⁺·2IO₃⁻, exhibits two crystallographically independent iodate anions, the I atoms of which are each in a trigonal–pyramidal environment. In the dication, the two pyridine rings adopt an anti conformation with respect to each other; the angle between these two rings is 3.84 (19)°. In the crystal structure, C—H⋯O hydrogen bonds between the cations and anions lead to the formation of layers arranged parallel to the ab plane. I⋯O halogen bonds [R₂²(4) graph-set motif] range between 2.873 (2) and 3.036 (3) Å and connect neighbouring IO₃⁻ anions with each other along [100], so as to create a three-dimensional network.

Related literature

For background about the oxidative properties of the iodate anion, see: Tamami et al. (2003 ); Singh et al. (2008 ). For related structures, see: Gholizadeh et al. (2011 ); Petrosyan et al. (1999 , 2000 ). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ). For the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₂H₁₄N₂²⁺·2IO₃⁻
M_r = 536.05
Monoclinic, P 2₁ /n
a = 7.9357 (4) Å
b = 10.2310 (4) Å
c = 18.6041 (9) Å
β = 91.017 (4)°
V = 1510.23 (12) Å³
Z = 4
Mo Kα radiation
μ = 4.20 mm⁻¹
T = 298 K
0.34 × 0.24 × 0.23 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005 )]T_min = 0.310, T_max = 0.379
10467 measured reflections
4032 independent reflections
3081 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.054
S = 1.01
4032 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O3ⁱ	0.93	2.22	3.095 (5)	157
C3—H3⋯O2ⁱⁱ	0.93	2.37	3.133 (5)	139
C5—H5⋯O4ⁱⁱⁱ	0.93	2.42	3.210 (5)	143
C6—H6B⋯O4ⁱ	0.97	2.37	3.230 (5)	148
C7—H7A⋯O2	0.97	2.52	3.420 (4)	154
C7—H7B⋯O1ⁱ	0.97	2.40	3.311 (5)	156
C8—H8⋯O1ⁱ	0.93	2.41	3.225 (5)	146
C9—H9⋯O1^iv	0.93	2.49	3.297 (4)	146
C10—H10⋯O6^v	0.93	2.18	3.051 (5)	156
C12—H12⋯O5ⁱⁱⁱ	0.93	2.07	2.982 (5)	167
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x+1, y, z; (iv) x, y-1, z; (v) x+1, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020927/zl2372sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020927/zl2372Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020927/zl2372Isup3.cml

checkCIF report

Comment top

The iodate anion has the capability to oxidize various functional groups, so a range of salts of this anion, such as the potassium salt, have been prepared (Singh et al., 2008). Iodate salts are also available supported on the commercial anionic resin Amberlyst A26, and also on poly(vinylpyridine) (Tamami et al., 2003). In a recent publication, we described the synthesis and crystal structure of bis pyridinium 1,2-ethane periodate (Gholizadeh et al., 2011). Here, we report the synthesis and single-crystal X-ray structure determination of the title iodate salt. Single crystals were obtained from CH₃CN at room temperature. The asymmetric unit of the title salt, C₁₂H₁₄N₂²⁺.2IO₃^- (Fig. 1), contains two crystallographically independent iodate anions and one bis pyridinium 1,2-ethane dication. Each of the I atoms in the iodate anions adopts a trigonal pyramidal geometry, the bond angles at the I atoms vary in the range from 101.03 (12)° to 101.31 (13)° for I1 and 98.89 (14)° to 102.12 (18)° for I2. The I—O bond lengths (in the range from 1.779 (3) Å to 1.803 (3) Å) and the O—I—O bond angles are comparable to those in similar compounds like for example in [C₆H₁₆N₂O₂]²⁺[HI₂O₆]^1-[IO₃]^1- (Petrosyan et al., 1999).

In the dication, the two pyridine moieties adopt an anti orientation with respect to one another. Some C—H···O hydrogen bonds, with C···O distances in the range from 2.888 (4) Å to 3.420 (4) Å, lead to a 2-D aggregation parallel to (001), Table 1 and Fig. 2. The I···O contacts (I1···O5ⁱ = 2.873 (2) Å, O3—I1···O5ⁱ = 163.07 (10)°, symmetry code: (i) 1 + x, y, z; O3···I2 = 2.961 (3) Å, I1—O3···I2 = 111.02 (13)°; I1···O5ⁱⁱ = 3.000 (3) Å, O1—I1···O5ⁱⁱ = 169.45 (11)°, symmetry code: (ii) 1 - x, 1 - y, 2 - z; I2···O2ⁱⁱ = 3.036 (3) Å, I2···O2ⁱⁱ—I1ⁱⁱ = 99.84°, symmetry code: (ii) 1 - x, 1 - y, 2 - z) involve IO₃^- anions with each other, building R₂²(4) rings along the a axis, which connect the two-dimensional structure into a three-dimensional network (Fig. 3). The I···O distances are comparable to those in similar iodate salts (CSD, Version 5.32, November 2010 update; Allen, 2002) e.g. in bis(β-alaninium) bis(iodate) monohydrate (CSD refcode ICAYAM; Petrosyan et al., 2000). Consistent with the n-σ* character of the I···O halogen bond, the shortening of the I···O interaction distance leads to lengthening of the corresponding O—I covalent bond. The usual motif, which is found for iodate salts, is a four-membered ring containing two O and two I atoms and four I···O halogen bonds; however, a few other motifs are also found for crystal packing based on halogen bonds (CSD refcode ICAYEQ; Petrosyan et al., 2000).

Related literature top

For background about the oxidative properties of iodate anions, see: Tamami et al. (2003); Singh et al. (2008). For related structures, see: Gholizadeh et al. (2011); Petrosyan et al. (1999, 2000). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995). For the Cambridge Structural Database, see: Allen (2002).

Experimental top

Preparation of bis pyridinium 1,2-ethane dibromide: 1,2-Dibromoethane (22 mmol) was added to pyridine (44.8 mmol) and dimethylformamide (40 ml) and refluxed. After 2 h, the precipitate was filtered and washed with diethyl ether and dried.

Preparation of title salt: To a solution of bis pyridinium 1,2-ethane dibromide (10 mmol) in H₂O (25 ml), a solution of NaIO₃ (20 mmol) in H₂O (25 ml) was added and stirred. After 1 h, the precipitate was filtered and washed with H₂O and crystallized from CH₃CN at room temperature (yield: approximately 60%). ¹H NMR (500.13 MHz, DMSO-d₆, 300 K, TMS): 5.23 (s, 4H, 2CH₂), 8.21 (t, 4H, Ar—H), 8.69 (t, 2H, Ar—H), 8.96 p.p.m. (d, 4H, Ar—H). ¹³C NMR (125.76 MHz, 300 K, TMS): 60.63, 129.36, 146.18, 147.54 p.p.m.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure and atom labelling scheme for title salt with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of title compound with C—H···O hydrogen bonds shown as dotted lines. The two crystallographically independent iodate anions are shown in green and red colours, respectively, and the dication is coloured blue.
	Fig. 3. Part of the crystal packing showing the C—H···O hydrogen bonds and the I···O halogen bonds. The two crystallographically independent iodate anions are shown in green and red colours, respectively, and the dication is coloured blue.

1,1'-(Ethane-1,2-diyl)dipyridinium bis(iodate) top

Crystal data top

C₁₂H₁₄N₂²⁺·2IO₃⁻	F(000) = 1016
M_r = 536.05	D_x = 2.358 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 435 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.9357 (4) Å	Cell parameters from 4032 reflections
b = 10.2310 (4) Å	θ = 2.2–29.2°
c = 18.6041 (9) Å	µ = 4.20 mm⁻¹
β = 91.017 (4)°	T = 298 K
V = 1510.23 (12) Å³	Prism, yellow
Z = 4	0.34 × 0.24 × 0.23 mm

Data collection top

Stoe IPDS II diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	3081 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 0.15 pixels mm^-1	θ_max = 29.2°, θ_min = 2.2°
rotation method scans	h = −8→10
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)]	k = −12→14
T_min = 0.310, T_max = 0.379	l = −25→25
10467 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0252P)²] where P = (F_o² + 2F_c²)/3
4032 reflections	(Δ/σ)_max = 0.002
199 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₂H₁₄N₂²⁺·2IO₃⁻	V = 1510.23 (12) Å³
M_r = 536.05	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9357 (4) Å	µ = 4.20 mm⁻¹
b = 10.2310 (4) Å	T = 298 K
c = 18.6041 (9) Å	0.34 × 0.24 × 0.23 mm
β = 91.017 (4)°

Data collection top

Stoe IPDS II diffractometer	4032 independent reflections
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)]	3081 reflections with I > 2σ(I)
T_min = 0.310, T_max = 0.379	R_int = 0.036
10467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.01	Δρ_max = 0.72 e Å⁻³
4032 reflections	Δρ_min = −0.74 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq
I1	0.83152 (3)	0.624927 (17)	0.927824 (10)	0.02673 (6)
O1	0.8505 (4)	0.6730 (3)	0.83552 (12)	0.0460 (6)
N1	1.0346 (4)	0.4963 (3)	0.69249 (13)	0.0308 (6)
O2	0.7306 (4)	0.4690 (2)	0.91801 (14)	0.0494 (7)
C5	1.0641 (5)	0.6193 (3)	0.71494 (18)	0.0369 (8)
H5	1.1127	0.6341	0.7601	0.044*
O3	0.6578 (4)	0.7251 (3)	0.95556 (14)	0.0479 (6)
C1	0.9644 (5)	0.4709 (4)	0.62715 (17)	0.0392 (8)
H1	0.9464	0.3852	0.6123	0.047*
C7	0.9171 (5)	0.3298 (3)	0.77240 (18)	0.0371 (8)
H7A	0.8658	0.3941	0.8035	0.045*
H7B	0.8373	0.3088	0.7340	0.045*
C2	0.9203 (5)	0.5730 (4)	0.58323 (18)	0.0483 (10)
H2	0.8709	0.5568	0.5384	0.058*
C6	1.0776 (5)	0.3854 (3)	0.7409 (2)	0.0412 (8)
H6A	1.1523	0.4151	0.7793	0.049*
H6B	1.1354	0.3180	0.7142	0.049*
C4	1.0226 (6)	0.7226 (4)	0.67134 (19)	0.0473 (10)
H4	1.0442	0.8078	0.6863	0.057*
C3	0.9487 (6)	0.6991 (4)	0.6051 (2)	0.0504 (10)
H3	0.9182	0.7685	0.5754	0.061*
N2	0.9590 (4)	0.2100 (3)	0.81418 (13)	0.0316 (6)
C8	0.9223 (5)	0.0913 (3)	0.78694 (18)	0.0346 (7)
H8	0.8662	0.0836	0.7428	0.042*
C12	1.0371 (6)	0.2234 (4)	0.87829 (19)	0.0467 (10)
H12	1.0576	0.3064	0.8969	0.056*
C9	0.9685 (5)	−0.0187 (3)	0.82504 (18)	0.0404 (8)
H9	0.9432	−0.1010	0.8066	0.048*
C11	1.0868 (6)	0.1146 (4)	0.9166 (2)	0.0515 (11)
H11	1.1442	0.1238	0.9603	0.062*
C10	1.0514 (5)	−0.0078 (4)	0.8899 (2)	0.0442 (9)
H10	1.0833	−0.0821	0.9155	0.053*
I2	0.33160 (3)	0.593964 (19)	0.925200 (11)	0.02945 (6)
O5	0.1485 (3)	0.4896 (2)	0.92384 (14)	0.0438 (6)
O4	0.3671 (4)	0.6018 (4)	0.83116 (14)	0.0749 (12)
O6	0.2414 (4)	0.7504 (3)	0.94274 (19)	0.0656 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02842 (11)	0.02451 (10)	0.02716 (9)	−0.00238 (8)	−0.00252 (7)	0.00285 (7)
O1	0.0538 (17)	0.0565 (17)	0.0277 (11)	−0.0048 (13)	−0.0004 (11)	0.0123 (10)
N1	0.0380 (16)	0.0258 (13)	0.0286 (12)	0.0015 (11)	−0.0018 (11)	0.0048 (9)
O2	0.0594 (18)	0.0343 (13)	0.0544 (15)	−0.0173 (13)	−0.0005 (13)	−0.0029 (11)
C5	0.047 (2)	0.0340 (17)	0.0299 (16)	−0.0026 (15)	−0.0014 (14)	−0.0013 (12)
O3	0.0406 (16)	0.0450 (15)	0.0582 (16)	0.0126 (12)	−0.0007 (12)	−0.0046 (12)
C1	0.046 (2)	0.0359 (18)	0.0360 (17)	−0.0001 (16)	−0.0035 (15)	−0.0060 (13)
C7	0.044 (2)	0.0264 (16)	0.0404 (17)	0.0055 (15)	−0.0051 (15)	0.0099 (13)
C2	0.053 (3)	0.063 (3)	0.0291 (17)	0.007 (2)	−0.0044 (16)	0.0034 (16)
C6	0.041 (2)	0.0327 (18)	0.050 (2)	0.0020 (15)	−0.0076 (16)	0.0124 (14)
C4	0.068 (3)	0.0268 (17)	0.047 (2)	0.0056 (17)	0.0094 (19)	0.0022 (14)
C3	0.060 (3)	0.045 (2)	0.046 (2)	0.0159 (19)	0.0063 (18)	0.0194 (16)
N2	0.0399 (16)	0.0245 (13)	0.0303 (13)	0.0009 (11)	−0.0042 (11)	0.0013 (9)
C8	0.040 (2)	0.0324 (17)	0.0317 (16)	−0.0021 (14)	0.0018 (14)	−0.0041 (12)
C12	0.070 (3)	0.0299 (17)	0.0399 (18)	−0.0026 (18)	−0.0132 (18)	−0.0030 (14)
C9	0.051 (2)	0.0248 (16)	0.0453 (19)	−0.0029 (15)	0.0054 (16)	−0.0021 (13)
C11	0.069 (3)	0.041 (2)	0.043 (2)	−0.0026 (19)	−0.019 (2)	0.0085 (15)
C10	0.052 (2)	0.0284 (17)	0.053 (2)	0.0031 (16)	−0.0008 (17)	0.0099 (14)
I2	0.02761 (12)	0.03071 (11)	0.02985 (10)	−0.00204 (9)	−0.00418 (8)	0.00538 (7)
O5	0.0388 (15)	0.0344 (13)	0.0581 (15)	−0.0117 (11)	−0.0027 (11)	−0.0044 (11)
O4	0.054 (2)	0.142 (4)	0.0285 (14)	−0.014 (2)	−0.0028 (13)	0.0167 (15)
O6	0.063 (2)	0.0259 (14)	0.106 (2)	0.0098 (14)	−0.0290 (18)	−0.0010 (14)

Geometric parameters (Å, º) top

I1—O2	1.793 (2)	C4—C3	1.376 (5)
I1—O1	1.795 (2)	C4—H4	0.9300
I1—O3	1.801 (3)	C3—H3	0.9300
N1—C5	1.345 (4)	N2—C12	1.341 (4)
N1—C1	1.353 (4)	N2—C8	1.346 (4)
N1—C6	1.485 (4)	C8—C9	1.376 (5)
C5—C4	1.369 (5)	C8—H8	0.9300
C5—H5	0.9300	C12—C11	1.375 (5)
C1—C2	1.367 (5)	C12—H12	0.9300
C1—H1	0.9300	C9—C10	1.368 (5)
C7—N2	1.486 (4)	C9—H9	0.9300
C7—C6	1.522 (5)	C11—C10	1.375 (5)
C7—H7A	0.9700	C11—H11	0.9300
C7—H7B	0.9700	C10—H10	0.9300
C2—C3	1.371 (6)	I2—O4	1.779 (3)
C2—H2	0.9300	I2—O6	1.786 (3)
C6—H6A	0.9700	I2—O5	1.803 (3)
C6—H6B	0.9700

O2—I1—O1	101.03 (12)	C5—C4—C3	119.3 (4)
O2—I1—O3	101.10 (14)	C5—C4—H4	120.3
O1—I1—O3	101.31 (13)	C3—C4—H4	120.3
C5—N1—C1	121.7 (3)	C2—C3—C4	119.7 (3)
C5—N1—C6	119.3 (3)	C2—C3—H3	120.1
C1—N1—C6	119.0 (3)	C4—C3—H3	120.1
N1—C5—C4	120.0 (3)	C12—N2—C8	121.4 (3)
N1—C5—H5	120.0	C12—N2—C7	118.5 (3)
C4—C5—H5	120.0	C8—N2—C7	120.2 (3)
N1—C1—C2	119.2 (3)	N2—C8—C9	119.3 (3)
N1—C1—H1	120.4	N2—C8—H8	120.3
C2—C1—H1	120.4	C9—C8—H8	120.3
N2—C7—C6	109.2 (3)	N2—C12—C11	120.1 (3)
N2—C7—H7A	109.8	N2—C12—H12	119.9
C6—C7—H7A	109.8	C11—C12—H12	119.9
N2—C7—H7B	109.8	C10—C9—C8	120.5 (3)
C6—C7—H7B	109.8	C10—C9—H9	119.8
H7A—C7—H7B	108.3	C8—C9—H9	119.8
C1—C2—C3	120.1 (3)	C10—C11—C12	119.7 (4)
C1—C2—H2	119.9	C10—C11—H11	120.2
C3—C2—H2	119.9	C12—C11—H11	120.2
N1—C6—C7	109.5 (3)	C9—C10—C11	119.0 (3)
N1—C6—H6A	109.8	C9—C10—H10	120.5
C7—C6—H6A	109.8	C11—C10—H10	120.5
N1—C6—H6B	109.8	O4—I2—O6	102.12 (18)
C7—C6—H6B	109.8	O4—I2—O5	98.89 (14)
H6A—C6—H6B	108.2	O6—I2—O5	101.98 (14)

C1—N1—C5—C4	0.1 (6)	C6—C7—N2—C12	74.0 (4)
C6—N1—C5—C4	−179.0 (4)	C6—C7—N2—C8	−104.5 (4)
C5—N1—C1—C2	−0.9 (6)	C12—N2—C8—C9	−1.2 (6)
C6—N1—C1—C2	178.2 (4)	C7—N2—C8—C9	177.2 (3)
N1—C1—C2—C3	0.7 (6)	C8—N2—C12—C11	2.3 (6)
C5—N1—C6—C7	104.7 (4)	C7—N2—C12—C11	−176.1 (4)
C1—N1—C6—C7	−74.4 (4)	N2—C8—C9—C10	−0.2 (6)
N2—C7—C6—N1	173.7 (3)	N2—C12—C11—C10	−2.1 (7)
N1—C5—C4—C3	0.9 (6)	C8—C9—C10—C11	0.4 (6)
C1—C2—C3—C4	0.3 (6)	C12—C11—C10—C9	0.7 (7)
C5—C4—C3—C2	−1.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O3ⁱ	0.93	2.22	3.095 (5)	157
C3—H3···O2ⁱⁱ	0.93	2.37	3.133 (5)	139
C5—H5···O1	0.93	2.56	2.888 (4)	101
C5—H5···O4ⁱⁱⁱ	0.93	2.42	3.210 (5)	143
C6—H6B···O4ⁱ	0.97	2.37	3.230 (5)	148
C7—H7A···O2	0.97	2.52	3.420 (4)	154
C7—H7B···O1ⁱ	0.97	2.40	3.311 (5)	156
C8—H8···O1ⁱ	0.93	2.41	3.225 (5)	146
C9—H9···O1^iv	0.93	2.49	3.297 (4)	146
C10—H10···O6^v	0.93	2.18	3.051 (5)	156
C12—H12···O5ⁱⁱⁱ	0.93	2.07	2.982 (5)	167

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) x, y−1, z; (v) x+1, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂²⁺·2IO₃⁻
M_r	536.05
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.9357 (4), 10.2310 (4), 18.6041 (9)
β (°)	91.017 (4)
V (Å³)	1510.23 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.20
Crystal size (mm)	0.34 × 0.24 × 0.23

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005)]
T_min, T_max	0.310, 0.379
No. of measured, independent and observed [I > 2σ(I)] reflections	10467, 4032, 3081
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.054, 1.01
No. of reflections	4032
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.74

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O3ⁱ	0.9300	2.2200	3.095 (5)	157.00
C3—H3···O2ⁱⁱ	0.9300	2.3700	3.133 (5)	139.00
C5—H5···O1	0.9300	2.5600	2.888 (4)	101.00
C5—H5···O4ⁱⁱⁱ	0.9300	2.4200	3.210 (5)	143.00
C6—H6B···O4ⁱ	0.9700	2.3700	3.230 (5)	148.00
C7—H7A···O2	0.9700	2.5200	3.420 (4)	154.00
C7—H7B···O1ⁱ	0.9700	2.4000	3.311 (5)	156.00
C8—H8···O1ⁱ	0.9300	2.4100	3.225 (5)	146.00
C9—H9···O1^iv	0.9300	2.4900	3.297 (4)	146.00
C10—H10···O6^v	0.9300	2.1800	3.051 (5)	156.00
C12—H12···O5ⁱⁱⁱ	0.9300	2.0700	2.982 (5)	167.00

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) x, y−1, z; (v) x+1, y−1, z.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

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