2-Meth­oxy­ethanaminium periodate 18-crown-6 clathrate

Hu, J.-G.

doi:10.1107/S1600536811002315

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o472-o473

doi:10.1107/S1600536811002315

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2-Methoxyethanaminium periodate 18-crown-6 clathrate

Jin-Gang Hu ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: jinganghu163@163.com

(Received 28 December 2010; accepted 15 January 2011; online 22 January 2011)

In the crystal structure of the title organic salt, C₃H₁₀NO⁺·IO₄⁻·C₁₂H₂₄O₆, the protonated 2-methoxyethanaminium (CH₃OC₂H₄—NH₃⁺) cation forms a 1:1 supramolecular rotator–stator complex with the 18-crown-6 molecule via N—H⋯O hydrogen bonds. The (CH₃OC₂H₄—NH₃⁺) group is attached from the convex side of the bowl-shaped crown, in contrast to similar ammonium cations that nest in the curvature of the bowl. The cations are associated via N—H⋯O interactions, while the cations and anions are linked by weak C—H⋯O hydrogen bonds, forming cation–crown–anion chains parallel to [010].

Related literature

For the use of crown ethers in catalysis, solvent extraction, isotope separation, bionics, materials chemistry, host–guest chemistry and supramolecular chemistry, see: Clark et al. (1998 ); Nakamura et al. (1998 ). For their ability to form non-covalent hydrogen-bonded complexes with ammonium cations, both in the solid state and in solution, see: Fender et al. (2002 ); Kryatova et al. (2004 ). Various types of RNH₃⁺ structures (R = H, CH₃, C₆H₅CH₂, NH₂, etc.) have been shown to form stable ammonium crown ether complexes in the solid state, see: Akutagawa et al. (2005 , 2009 ). For a related structure, see: Fu et al. (2010 ).

Experimental

Crystal data

C₃H₁₀NO⁺·IO₄⁻·C₁₂H₂₄O₆
M_r = 531.33
Monoclinic, P 2₁ /c
a = 13.118 (3) Å
b = 8.4229 (17) Å
c = 22.176 (7) Å
β = 111.81 (3)°
V = 2274.9 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.747, T_max = 0.754
22779 measured reflections
5201 independent reflections
4138 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.146
S = 1.05
5201 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 1.74 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—H1C⋯O1	0.89	2.30	3.000 (4)	135
N1—H1C⋯O2	0.89	2.15	2.912 (4)	144
N1—H1D⋯O3	0.89	2.43	2.980 (5)	121
N1—H1D⋯O4	0.89	2.03	2.886 (4)	161
N1—H1E⋯O5	0.89	2.43	3.010 (5)	123
N1—H1E⋯O6	0.89	2.06	2.870 (4)	151
C1—H1B⋯O11ⁱ	0.97	2.54	3.398 (9)	148
C13—H13A⋯O8	0.97	2.52	3.288 (7)	135
C13—H13B⋯O1ⁱⁱ	0.97	2.54	3.504 (6)	171
C15—H15B⋯O10ⁱⁱⁱ	0.96	2.47	3.370 (9)	156
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002315/vm2071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002315/vm2071Isup2.hkl

checkCIF report

Comment top

The ability of 18-crown-6 ether (18-C-6) to form complexes with different metal ions and organic proton donors has been widely investigated. Because of their novel coordination modes, crown ethers have been widely used in catalysis, solvent extraction, isotope separation, bionics, materials chemistry, host-guest chemistry and supramolecular chemistry (Clark et al., 1998; Nakamura et al., 1998). Crown ethers recnetly have attracted much attention due to their ability to form non-covalent hydrogen-bonded complexes with ammonium cations, both in the solid state and in solution (Fender et al., 2002; Kryatova et al., 2004). The structures of organic ammonium RNH₃⁺.crown ether assemblies in the solid state depend not only on the structure of the cation and the size of the crown ether ring, but also on the nature of the counter-anion. Various types of RNH₃⁺structures (R =H, CH₃, C₆H₅CH₂, NH₂, etc.) have been shown to form stable ammonium.crown ether complexes in the solid state (Akutagawa et al., 2005, 2009).

We report here the crystal structure of 2-methoxy-ethylamine periodate 18-crown-6 clathrate. X-ray crystallographic studies have been carried out for the complex C₃H₉NO^+.IO₄^-.C₁₂H₂₄O₆ at room temperature. An view of the complex is shown in Fig. 1. The ionic radius of NH₃⁺ matches the cavity size of six-O crown ethers, and N—H···O hydrogen bonds (Table 1) help to form stable NH₃⁺.crown ether complexes, displayed in Fig. 2.

Related literature top

For the use of crown ethers in catalysis, solvent extraction, isotope separation, bionics, materials chemistry, host–guest chemistry and supramolecular chemistry, see: Clark et al. (1998); Nakamura et al. (1998). For their ability to form non-covalent hydrogen-bonded complexes with ammonium cations, both in the solid state and in solution, see: Fender et al. (2002); Kryatova et al. (2004). Various types of RNH₃⁺ structures (R = H, CH₃, C₆H₅CH₂, NH₂, etc.) have been shown to form stable ammonium crown ether complexes in the solid state, see: Akutagawa et al. (2005, 2009). For a related structure, see: Fu et al. (2010). AUTHOR: remember to subdivide this section in future

Experimental top

2-Methoxy-ethylamine (1.50 g, 0.02 mol), 18-crown-6 (5.28 g, 0.02 mol) and HIO₄ (4.56 g, 0.02 mol) were dissolved in 30 ml ethanol. Colorless s//ingle crystals of the title compound suitable for X-ray analysis were obtained via slow evaporation of the solvent at room temperature over a period of 3 days.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme (H atom labels have been omitted for clarity). Displacement ellipsoids are drawn at the 30% probability level, and N—H···O hydrogen bonds are shown as dotted lines.
	Fig. 2. Crystal packing of the title compound viewed along the a axis showing the N—H···O and, C—H···O interactions (dotted lines).

2-Methoxyethanaminium periodate–18-crown-6 (1/1) top

Crystal data top

C₃H₁₀NO⁺·IO₄⁻·C₁₂H₂₄O₆	F(000) = 1088
M_r = 531.33	D_x = 1.551 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 121476 reflections
a = 13.118 (3) Å	θ = 3.0–27.5°
b = 8.4229 (17) Å	µ = 1.46 mm⁻¹
c = 22.176 (7) Å	T = 293 K
β = 111.81 (3)°	Prism, white
V = 2274.9 (10) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	5201 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD_Profile_fitting scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −10→10
T_min = 0.747, T_max = 0.754	l = −28→28
22779 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0576P)² + 3.350P] where P = (F_o² + 2F_c²)/3
5201 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 1.74 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

C₃H₁₀NO⁺·IO₄⁻·C₁₂H₂₄O₆	V = 2274.9 (10) Å³
M_r = 531.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.118 (3) Å	µ = 1.46 mm⁻¹
b = 8.4229 (17) Å	T = 293 K
c = 22.176 (7) Å	0.20 × 0.20 × 0.20 mm
β = 111.81 (3)°

Data collection top

Rigaku SCXmini diffractometer	5201 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4138 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.754	R_int = 0.067
22779 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.05	Δρ_max = 1.74 e Å⁻³
5201 reflections	Δρ_min = −1.26 e Å⁻³
253 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.5224 (5)	0.6622 (8)	0.1488 (3)	0.0852 (19)
H1A	0.5451	0.7725	0.1528	0.102*
H1B	0.5460	0.6124	0.1167	0.102*
C2	0.5742 (5)	0.5819 (7)	0.2115 (4)	0.088 (2)
H2A	0.5480	0.4733	0.2081	0.106*
H2B	0.6531	0.5792	0.2231	0.106*
C3	0.6022 (4)	0.5926 (7)	0.3233 (3)	0.088 (2)
H3A	0.6812	0.5962	0.3353	0.106*
H3B	0.5805	0.4822	0.3222	0.106*
C4	0.5719 (5)	0.6786 (7)	0.3718 (3)	0.089 (2)
H4A	0.6127	0.6368	0.4148	0.107*
H4B	0.5898	0.7903	0.3714	0.107*
C5	0.4229 (8)	0.7282 (8)	0.4040 (3)	0.101 (3)
H5A	0.4449	0.8388	0.4105	0.121*
H5B	0.4571	0.6731	0.4450	0.121*
C6	0.3006 (8)	0.7164 (8)	0.3824 (3)	0.097 (2)
H6A	0.2781	0.6061	0.3748	0.117*
H6B	0.2770	0.7578	0.4159	0.117*
C7	0.1360 (6)	0.8074 (10)	0.3024 (4)	0.102 (3)
H7A	0.1129	0.8481	0.3362	0.122*
H7B	0.1072	0.7007	0.2916	0.122*
C8	0.0934 (5)	0.9077 (9)	0.2455 (4)	0.100 (2)
H8A	0.0147	0.9201	0.2330	0.120*
H8B	0.1270	1.0119	0.2552	0.120*
C9	0.0830 (4)	0.9315 (7)	0.1374 (3)	0.092 (2)
H9A	0.1256	1.0288	0.1459	0.110*
H9B	0.0063	0.9596	0.1252	0.110*
C10	0.0982 (5)	0.8449 (8)	0.0838 (3)	0.091 (2)
H10A	0.0604	0.7437	0.0774	0.109*
H10B	0.0672	0.9057	0.0439	0.109*
C11	0.2322 (7)	0.7290 (8)	0.0503 (3)	0.096 (2)
H11A	0.1953	0.7769	0.0079	0.115*
H11B	0.2039	0.6222	0.0492	0.115*
C12	0.3523 (7)	0.7235 (8)	0.0657 (3)	0.093 (2)
H12A	0.3674	0.6618	0.0330	0.111*
H12B	0.3801	0.8302	0.0656	0.111*
C13	0.2704 (4)	0.4729 (5)	0.2349 (2)	0.0524 (10)
H13A	0.2642	0.4720	0.2772	0.063*
H13B	0.3262	0.3962	0.2360	0.063*
C14	0.1627 (4)	0.4234 (5)	0.1843 (2)	0.0554 (10)
H14A	0.1361	0.3280	0.1982	0.066*
H14B	0.1086	0.5067	0.1780	0.066*
C15	0.0806 (5)	0.3509 (7)	0.0747 (3)	0.0828 (17)
H15A	0.0963	0.3330	0.0362	0.124*
H15B	0.0274	0.4344	0.0667	0.124*
H15C	0.0518	0.2553	0.0859	0.124*
I1	0.22495 (3)	0.22656 (4)	0.422019 (14)	0.06214 (15)
N1	0.3057 (2)	0.6331 (4)	0.22280 (14)	0.0400 (7)
H1C	0.3701	0.6565	0.2537	0.060*
H1D	0.2559	0.7045	0.2232	0.060*
H1E	0.3123	0.6344	0.1843	0.060*
O1	0.5496 (2)	0.6619 (4)	0.26073 (18)	0.0613 (8)
O2	0.4587 (3)	0.6605 (4)	0.35678 (15)	0.0729 (10)
O3	0.2523 (3)	0.8040 (5)	0.32505 (18)	0.0730 (10)
O4	0.1168 (3)	0.8372 (4)	0.1939 (2)	0.0724 (10)
O5	0.2119 (3)	0.8196 (4)	0.09849 (15)	0.0719 (10)
O6	0.4055 (3)	0.6534 (5)	0.12774 (16)	0.0705 (9)
O7	0.1787 (3)	0.3952 (5)	0.12675 (15)	0.0679 (9)
O8	0.2020 (5)	0.2732 (6)	0.3416 (2)	0.1104 (17)
O9	0.1995 (5)	0.3899 (6)	0.4627 (3)	0.1233 (18)
O10	0.1278 (5)	0.0779 (7)	0.4205 (3)	0.132 (2)
O11	0.3531 (5)	0.1407 (11)	0.4607 (3)	0.161 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.096 (4)	0.079 (4)	0.117 (5)	−0.020 (3)	0.082 (4)	−0.032 (4)
C2	0.061 (3)	0.061 (3)	0.162 (7)	0.000 (3)	0.063 (4)	−0.021 (4)
C3	0.044 (3)	0.065 (3)	0.126 (5)	0.008 (2)	−0.003 (3)	0.024 (3)
C4	0.078 (4)	0.070 (3)	0.072 (3)	0.001 (3)	−0.026 (3)	0.012 (3)
C5	0.165 (8)	0.088 (4)	0.032 (2)	−0.017 (4)	0.016 (3)	−0.002 (2)
C6	0.165 (8)	0.096 (4)	0.057 (3)	−0.031 (4)	0.072 (4)	−0.017 (3)
C7	0.091 (5)	0.116 (5)	0.136 (7)	−0.032 (4)	0.085 (5)	−0.058 (5)
C8	0.060 (3)	0.097 (5)	0.149 (7)	0.001 (3)	0.046 (4)	−0.050 (5)
C9	0.056 (3)	0.056 (3)	0.121 (5)	0.012 (2)	−0.016 (3)	0.008 (3)
C10	0.080 (4)	0.074 (4)	0.070 (3)	−0.008 (3)	−0.028 (3)	0.016 (3)
C11	0.145 (7)	0.095 (4)	0.034 (3)	−0.042 (4)	0.018 (3)	−0.005 (2)
C12	0.153 (7)	0.093 (4)	0.048 (3)	−0.043 (4)	0.055 (4)	−0.012 (3)
C13	0.068 (3)	0.043 (2)	0.042 (2)	0.0030 (19)	0.0155 (19)	0.0039 (17)
C14	0.063 (3)	0.045 (2)	0.064 (3)	−0.0082 (19)	0.030 (2)	−0.0042 (19)
C15	0.092 (4)	0.068 (3)	0.063 (3)	−0.020 (3)	−0.002 (3)	−0.002 (3)
I1	0.0582 (2)	0.0813 (3)	0.0510 (2)	0.00434 (14)	0.02498 (15)	0.00660 (14)
N1	0.0372 (15)	0.0504 (18)	0.0316 (14)	0.0007 (13)	0.0120 (12)	−0.0011 (12)
O1	0.0419 (15)	0.0467 (16)	0.091 (2)	0.0054 (13)	0.0197 (15)	−0.0005 (16)
O2	0.086 (2)	0.073 (2)	0.0412 (17)	−0.016 (2)	0.0025 (16)	−0.0003 (16)
O3	0.090 (3)	0.077 (2)	0.069 (2)	−0.0169 (19)	0.050 (2)	−0.0153 (18)
O4	0.0525 (18)	0.0593 (19)	0.098 (3)	0.0103 (16)	0.0192 (18)	−0.0143 (19)
O5	0.083 (2)	0.070 (2)	0.0427 (17)	−0.0211 (19)	−0.0002 (16)	0.0024 (15)
O6	0.089 (2)	0.081 (2)	0.0587 (19)	−0.028 (2)	0.0482 (18)	−0.0149 (17)
O7	0.0594 (19)	0.090 (2)	0.0497 (17)	−0.0077 (17)	0.0150 (14)	−0.0147 (16)
O8	0.148 (5)	0.121 (4)	0.061 (3)	−0.016 (3)	0.037 (3)	0.022 (2)
O9	0.157 (5)	0.095 (3)	0.121 (4)	0.005 (3)	0.056 (4)	−0.032 (3)
O10	0.161 (5)	0.111 (4)	0.159 (5)	−0.040 (4)	0.101 (4)	−0.006 (4)
O11	0.096 (4)	0.278 (9)	0.102 (4)	0.072 (5)	0.030 (3)	0.018 (5)

Geometric parameters (Å, º) top

C1—O6	1.429 (7)	C9—H9A	0.9700
C1—C2	1.468 (9)	C9—H9B	0.9700
C1—H1A	0.9700	C10—O5	1.420 (7)
C1—H1B	0.9700	C10—H10A	0.9700
C2—O1	1.418 (7)	C10—H10B	0.9700
C2—H2A	0.9700	C11—O5	1.417 (7)
C2—H2B	0.9700	C11—C12	1.484 (11)
C3—O1	1.426 (7)	C11—H11A	0.9700
C3—C4	1.468 (9)	C11—H11B	0.9700
C3—H3A	0.9700	C12—O6	1.420 (7)
C3—H3B	0.9700	C12—H12A	0.9700
C4—O2	1.405 (7)	C12—H12B	0.9700
C4—H4A	0.9700	C13—N1	1.484 (5)
C4—H4B	0.9700	C13—C14	1.500 (6)
C5—O2	1.416 (8)	C13—H13A	0.9700
C5—C6	1.497 (11)	C13—H13B	0.9700
C5—H5A	0.9700	C14—O7	1.390 (5)
C5—H5B	0.9700	C14—H14A	0.9700
C6—O3	1.401 (8)	C14—H14B	0.9700
C6—H6A	0.9700	C15—O7	1.424 (6)
C6—H6B	0.9700	C15—H15A	0.9600
C7—O3	1.418 (8)	C15—H15B	0.9600
C7—C8	1.446 (11)	C15—H15C	0.9600
C7—H7A	0.9700	I1—O11	1.736 (5)
C7—H7B	0.9700	I1—O8	1.740 (4)
C8—O4	1.421 (7)	I1—O9	1.744 (5)
C8—H8A	0.9700	I1—O10	1.778 (5)
C8—H8B	0.9700	N1—H1C	0.8900
C9—O4	1.409 (7)	N1—H1D	0.8900
C9—C10	1.470 (9)	N1—H1E	0.8900

O6—C1—C2	110.4 (4)	O5—C10—H10A	109.8
O6—C1—H1A	109.6	C9—C10—H10A	109.8
C2—C1—H1A	109.6	O5—C10—H10B	109.8
O6—C1—H1B	109.6	C9—C10—H10B	109.8
C2—C1—H1B	109.6	H10A—C10—H10B	108.2
H1A—C1—H1B	108.1	O5—C11—C12	108.9 (5)
O1—C2—C1	110.7 (4)	O5—C11—H11A	109.9
O1—C2—H2A	109.5	C12—C11—H11A	109.9
C1—C2—H2A	109.5	O5—C11—H11B	109.9
O1—C2—H2B	109.5	C12—C11—H11B	109.9
C1—C2—H2B	109.5	H11A—C11—H11B	108.3
H2A—C2—H2B	108.1	O6—C12—C11	109.5 (5)
O1—C3—C4	110.2 (4)	O6—C12—H12A	109.8
O1—C3—H3A	109.6	C11—C12—H12A	109.8
C4—C3—H3A	109.6	O6—C12—H12B	109.8
O1—C3—H3B	109.6	C11—C12—H12B	109.8
C4—C3—H3B	109.6	H12A—C12—H12B	108.2
H3A—C3—H3B	108.1	N1—C13—C14	112.8 (3)
O2—C4—C3	108.9 (4)	N1—C13—H13A	109.0
O2—C4—H4A	109.9	C14—C13—H13A	109.0
C3—C4—H4A	109.9	N1—C13—H13B	109.0
O2—C4—H4B	109.9	C14—C13—H13B	109.0
C3—C4—H4B	109.9	H13A—C13—H13B	107.8
H4A—C4—H4B	108.3	O7—C14—C13	108.2 (4)
O2—C5—C6	110.3 (5)	O7—C14—H14A	110.1
O2—C5—H5A	109.6	C13—C14—H14A	110.1
C6—C5—H5A	109.6	O7—C14—H14B	110.1
O2—C5—H5B	109.6	C13—C14—H14B	110.1
C6—C5—H5B	109.6	H14A—C14—H14B	108.4
H5A—C5—H5B	108.1	O7—C15—H15A	109.5
O3—C6—C5	108.9 (5)	O7—C15—H15B	109.5
O3—C6—H6A	109.9	H15A—C15—H15B	109.5
C5—C6—H6A	109.9	O7—C15—H15C	109.5
O3—C6—H6B	109.9	H15A—C15—H15C	109.5
C5—C6—H6B	109.9	H15B—C15—H15C	109.5
H6A—C6—H6B	108.3	O11—I1—O8	111.6 (3)
O3—C7—C8	109.7 (5)	O11—I1—O9	114.1 (3)
O3—C7—H7A	109.7	O8—I1—O9	111.0 (3)
C8—C7—H7A	109.7	O11—I1—O10	105.8 (4)
O3—C7—H7B	109.7	O8—I1—O10	106.8 (3)
C8—C7—H7B	109.7	O9—I1—O10	107.0 (3)
H7A—C7—H7B	108.2	C13—N1—H1C	109.5
O4—C8—C7	109.2 (5)	C13—N1—H1D	109.5
O4—C8—H8A	109.8	H1C—N1—H1D	109.5
C7—C8—H8A	109.8	C13—N1—H1E	109.5
O4—C8—H8B	109.8	H1C—N1—H1E	109.5
C7—C8—H8B	109.8	H1D—N1—H1E	109.5
H8A—C8—H8B	108.3	C2—O1—C3	112.8 (5)
O4—C9—C10	110.3 (4)	C4—O2—C5	113.1 (5)
O4—C9—H9A	109.6	C6—O3—C7	113.4 (6)
C10—C9—H9A	109.6	C9—O4—C8	113.0 (5)
O4—C9—H9B	109.6	C10—O5—C11	112.5 (5)
C10—C9—H9B	109.6	C12—O6—C1	112.1 (5)
H9A—C9—H9B	108.1	C14—O7—C15	113.0 (4)
O5—C10—C9	109.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1	0.89	2.30	3.000 (4)	135
N1—H1C···O2	0.89	2.15	2.912 (4)	144
N1—H1D···O3	0.89	2.43	2.980 (5)	121
N1—H1D···O4	0.89	2.03	2.886 (4)	161
N1—H1E···O5	0.89	2.43	3.010 (5)	123
N1—H1E···O6	0.89	2.06	2.870 (4)	151
C1—H1B···O11ⁱ	0.97	2.54	3.398 (9)	148
C13—H13A···O8	0.97	2.52	3.288 (7)	135
C13—H13B···O1ⁱⁱ	0.97	2.54	3.504 (6)	171
C15—H15B···O10ⁱⁱⁱ	0.96	2.47	3.370 (9)	156

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

Experimental details

Crystal data
Chemical formula	C₃H₁₀NO⁺·IO₄⁻·C₁₂H₂₄O₆
M_r	531.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.118 (3), 8.4229 (17), 22.176 (7)
β (°)	111.81 (3)
V (Å³)	2274.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.747, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	22779, 5201, 4138
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.146, 1.05
No. of reflections	5201
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −1.26

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1	0.89	2.30	3.000 (4)	135
N1—H1C···O2	0.89	2.15	2.912 (4)	144
N1—H1D···O3	0.89	2.43	2.980 (5)	121
N1—H1D···O4	0.89	2.03	2.886 (4)	161
N1—H1E···O5	0.89	2.43	3.010 (5)	123
N1—H1E···O6	0.89	2.06	2.870 (4)	151
C1—H1B···O11ⁱ	0.97	2.54	3.398 (9)	148
C13—H13A···O8	0.97	2.52	3.288 (7)	135
C13—H13B···O1ⁱⁱ	0.97	2.54	3.504 (6)	171
C15—H15B···O10ⁱⁱⁱ	0.96	2.47	3.370 (9)	156

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

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

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