Literature DB >> 21837022

1,1'-(Ethane-1,2-di-yl)dipyridinium bis-(iodate).

Mostafa Gholizadeh, Behrooz Maleki, Mehrdad Pourayoubi, Mehdi Kia, Behrouz Notash.

Abstract

The title salt, C(12)H(14)N(2) (2+)·2IO(3) (-), 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 [R(2) (2)(4) graph-set motif] range between 2.873 (2) and 3.036 (3) Å and connect neighbouring IO(3) (-) anions with each other along [100], so as to create a three-dimensional network.

Entities: Chemical Disease Species

Year: 2011 PMID： 21837022 PMCID： PMC3151914 DOI： 10.1107/S1600536811020927

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

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

C12H14N2 2+·2IO3 − M = 536.05 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.054 S = 1.01 4032 reflections 199 parameters H-atom parameters constrained Δρmax = 0.72 e Å−3 Δρmin = −0.74 e Å−3 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 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020927/zl2372sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020927/zl2372Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811020927/zl2372Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Stoe IPDS II diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	3081 reflections with I > 2σ(I)
graphite	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 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

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.

	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)

	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)

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)

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.

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) ; (ii) ; (iii) ; (iv) ; (v) .

3 in total

1 in total

1. 1,1'-(Ethane-1,2-di-yl)dipyridinium dichromate(VI).

Authors: Mostafa Gholizadeh; Mehrdad Pourayoubi; Mehdi Kia; Arnold L Rheingold; James A Golen
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-02-17