(4,7,13,16,21,24-Hexaoxa-1,10-diaza­bicyclo­[8.8.8]hexa­cosa­ne)sodium perchlorate

Guzei, I.A.; Su, J.W.; Spencer, L.C.; Burnette, R.R.

doi:10.1107/S1600536809039683

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1381-m1382

https://doi.org/10.1107/S1600536809039683

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(4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)sodium perchlorate

Ilia A. Guzei,^a ^* Joe W. Su,^b Lara C. Spencer ^a and Ronald R. Burnette ^c

^aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI 53706, USA, ^bDR SUSS CORP, 6007 McLeod Dr, Las Vegas, NV 89120, USA, and ^cSchool of Pharmacy, University of Wisconsin, 777 Highland Ave., Madison, WI 53705, USA
^*Correspondence e-mail: iguzei@chem.wisc.edu

(Received 13 August 2009; accepted 29 September 2009; online 17 October 2009)

The title compound, [Na(C₁₈H₃₆N₂O₆)]ClO₄, was isolated and crystallized to understand more fully the ligand's binding specificity to cations. The cation and anion reside at an intersection of crystallographic twofold and threefold axes. The carbon atoms in the cation are disordered over two positions in a 3:2 ratio, and the anion is equally disordered over two positions. The geometries of the cation and anion are typical. The compound packs in alternating sheets of discrete cations and anions stacked along the c axis, separated by a distance equal to one-sixth the length of the c axis.

Related literature

For general background to the macrocyclic polyether 4,7,13,16,21,24-hexaoxa-1,10-diaza-bicyclo[8.8.8]hexacosane, see: Izatt et al. (1985 ); Tait et al. (1997 ); Varga et al. (1994 ); Trend et al. (1993 ); Hamacher et al. (1986 ); Su & Burnette (2008 ). For related structures, see: Belaj et al. (1997 ); Tehan et al. (1974 ). For a description of the Cambridge Structural Database, see: Allen (2002 ) and for Mogul, see: Bruno et al. (2004 ).

Experimental

Crystal data

[Na(C₁₈H₃₆N₂O₆)]ClO₄
M_r = 498.93
Rhombohedral, R 32
a = 8.4730 (3) Å
c = 28.220 (3) Å
V = 1754.5 (2) Å³
Z = 3
Mo- Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.49 × 0.37 × 0.35 mm

Data collection

Bruker CCD-1000 area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.893, T_max = 0.922
6885 measured reflections
805 independent reflections
765 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 1.11
805 reflections
85 parameters
144 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), 319 Friedel pairs
Flack parameter: 0.01 (15)

Table 1
Selected geometric parameters (Å, °)

Cl1—O2ⁱ	1.422 (4)
Cl1—O2	1.422 (4)
Cl1—O3ⁱ	1.434 (3)
Cl1—O3ⁱⁱ	1.434 (3)
Cl1—O3	1.434 (3)
Cl1—O3ⁱⁱⁱ	1.434 (3)
Cl1—O3^iv	1.434 (3)
Cl1—O3^v	1.434 (3)
Na1—O1	2.5661 (15)
Na1—N1	2.684 (2)
O2—O3ⁱⁱⁱ	1.639 (5)
O3—O3^v	1.797 (10)
Symmetry codes: (i) y, x, -z+2; (ii) -y+2, x-y+1, z; (iii) x-y+1, -y+2, -z+2; (iv) -x+y+1, -x+2, z; (v) -x+2, -x+y+1, -z+2.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL, OLEX2 (Dolomanov et al., 2009 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL, modiCIFer (Guzei, 2007 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039683/hk2757sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039683/hk2757Isup2.hkl

checkCIF report

Comment top

The macrocyclic polyether 4,7,13,16,21,24-hexaoxa-1,10-diaza-bicyclo[8.8.8]hexacosane (222) is a classic example of a host molecule possessing important clinical functions. 222 encapsulates 1:1 various alkali and alkaline earth metals, and features high selectivity for K⁺ and Sr²⁺ in solution (Izatt et al., 1985). Tait et al. (1997) formulated a cation exchange resin treated with 222 that sorbed more than 95% of the fallout nuclide ⁹⁰Sr in liquid milk (295 K, pH 5.2, 4 h contact time, 1:50 resin to milk volume ratio). Varga et al. (1994) synthesized functionalized 222 for ⁸⁵Sr²⁺ decorporation in the rat and mouse. J. E. Trend and co-workers (1993) formulated 222 with a covalently bound chromophore to assay clinical blood K⁺⁴. Hamacher et al. (1986) developed the use of [K⁺(222)]¹⁸F^- as a phase transfer catalyst in synthesizing the clinically significant PET tracer 2-[¹⁸F]fluoro-2-deoxy-D-glucose. Due to 222 obvious industrial and clinical applications the relative binding characteristics of 222 to Li⁺, Na⁺ and K⁺ have been studied in order to more fully understand 222's binding specificity to cations (Su & Burnette, 2008).

In the title compound, (I), both the Na⁺(222) cation and the perchlorate anion of (I) reside at an intersection of crystallographic twofold and threefold axes. All the carbon atoms in the cation are disordered over two positions in a 3:2 ratio. The perchlorate anion is equally disordered over two positions. Multiple restraints were applied to ensure computational stability of the refinement.

The bond distances and angles within (I) are typical as confirmed by the Mogul structural check (Bruno et. al, 2004). Among 59 relevant compounds reported to the CSD (Allen, 2002), the most closely related is (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo(8.8.8)hexacosane)-sodium periodate which contains the same cation as (I) and a periodate anion instead of the perchlorate anion (Belaj et al., 1997), and sodium (2,2,2)-crypt-sodium (Tehan et al., 1974) which forms crystals in the same rhombohedral space group R32, as (I).

The packing structure of compound (I) consists of alternating sheets of cations and anions stacked along the c axis. The distance between these sheets is 4.70 Å, or one sixth of the length of the c axis.

Related literature top

For general backgroundto the macrocyclic polyether

4,7,13,16,21,24-hexaoxa-1,10-diaza-bicyclo[8.8.8]hexacosane, see: Izatt et al. (1985); Tait et al. (1997); Varga et al. (1994); Trend et al. (1993); Hamacher et al. (1986); Su & Burnette (2008). For related structures, see: Belaj et al. (1997); Tehan et al. (1974). For a description of the Cambridge Structural Database, see: Allen (2002) and for Mogul, see: Bruno et al. (2004).

Experimental top

An equimolar mixture of 222 and NaClO₄ was prepared in acetone. The mixture was allowed to evaporate slowly at room temperature until crystallization was observed.

Structure description top

For general backgroundto the macrocyclic polyether

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), modiCIFer (Guzei, 2007) and publCIF (Westrip, 2009).

Figures top

Fig. 1. Molecular structure of (I). The thermal ellipsoids are shown at 50% probability level. Only the preferred orientation of the carbon atoms is shown and only tone orientation of the perchlorate molecule is shown. All hydrogen atoms were omitted for clarity. Symmetry transformations used to generate equivalent atoms: i: (-x + y+1,-x + 1,z) ii: (-y + 1,x-y,z) iii: (-x + 4/3,-x + y+2/3,-z + 5/3) iv: (y + 1/3,x - 1/3,-z + 5/3) v: (x-y + 1/3,-y + 2/3,-z + 5/3) vi: (-x + y+1,-x + 2,z) vii: (-y + 2,x-y + 1,z).

(4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)sodium perchlorate top

Crystal data top

[Na(C₁₈H₃₆N₂O₆)]ClO₄	F(000) = 798
M_r = 498.93	D_x = 1.417 Mg m⁻³
Rhombohedral, R32	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: R 3 2"	Cell parameters from 999 reflections
a = 8.4730 (3) Å	θ = 2.2–26.4°
c = 28.220 (3) Å	µ = 0.24 mm⁻¹
α = 90°	T = 100 K
γ = 120°	Block, colorless
V = 1754.5 (2) Å³	0.49 × 0.37 × 0.35 mm
Z = 3

Data collection top

Bruker CCD-1000 area-detector diffractometer	805 independent reflections
Radiation source: fine-focus sealed tube	765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
0.30° ω scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.893, T_max = 0.922	k = −10→10
6885 measured reflections	l = −35→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0715P)² + 1.1083P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
805 reflections	Δρ_max = 0.28 e Å⁻³
85 parameters	Δρ_min = −0.18 e Å⁻³
144 restraints	Absolute structure: Flack (1983), 319 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (15)

Crystal data top

[Na(C₁₈H₃₆N₂O₆)]ClO₄	V = 1754.5 (2) Å³
M_r = 498.93	Z = 3
Rhombohedral, R32	Mo Kα radiation
a = 8.4730 (3) Å	µ = 0.24 mm⁻¹
c = 28.220 (3) Å	T = 100 K
α = 90°	0.49 × 0.37 × 0.35 mm
γ = 120°

Data collection top

Bruker CCD-1000 area-detector diffractometer	805 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	765 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.922	R_int = 0.026
6885 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.113	Δρ_max = 0.28 e Å⁻³
S = 1.11	Δρ_min = −0.18 e Å⁻³
805 reflections	Absolute structure: Flack (1983), 319 Friedel pairs
85 parameters	Absolute structure parameter: 0.01 (15)
144 restraints

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	Occ. (<1)
Cl1	1.0000	1.0000	1.0000	0.0347 (3)
Na1	0.6667	0.3333	0.8333	0.0246 (3)
O1	0.9844 (2)	0.5262 (3)	0.86993 (4)	0.0589 (6)
O2	1.0000	1.0000	0.94963 (15)	0.0768 (17)	0.50
O3	0.8972 (8)	0.8167 (4)	1.01732 (13)	0.0762 (10)	0.50
N1	0.6667	0.3333	0.92846 (8)	0.0420 (6)
C1	0.8527 (6)	0.3802 (11)	0.9424 (2)	0.0688 (15)	0.60
H1A	0.8634	0.3967	0.9772	0.083*	0.60
H1B	0.8694	0.2754	0.9348	0.083*	0.60
C1A	0.8443 (7)	0.4767 (11)	0.9471 (3)	0.0534 (16)	0.40
H1C	0.8525	0.5973	0.9452	0.064*	0.40
H1D	0.8581	0.4518	0.9807	0.064*	0.40
C2	1.0022 (10)	0.5443 (10)	0.92024 (13)	0.0614 (18)	0.60
H2A	0.9972	0.6535	0.9305	0.074*	0.60
H2B	1.1210	0.5592	0.9301	0.074*	0.60
C2A	0.9880 (17)	0.475 (3)	0.9180 (2)	0.087 (4)	0.40
H2C	1.1084	0.5602	0.9319	0.104*	0.40
H2D	0.9725	0.3514	0.9186	0.104*	0.40
C3	1.0622 (10)	0.7167 (5)	0.85941 (11)	0.087 (2)	0.60
H3A	1.1909	0.7854	0.8699	0.105*	0.60
H3B	0.9934	0.7671	0.8756	0.105*	0.60
C3A	1.1033 (9)	0.6727 (12)	0.8398 (4)	0.094 (4)	0.40
H3C	1.1327	0.6254	0.8110	0.113*	0.40
H3D	1.2183	0.7554	0.8565	0.113*	0.40

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0316 (3)	0.0316 (3)	0.0408 (5)	0.01580 (17)	0.000	0.000
Na1	0.0265 (4)	0.0265 (4)	0.0208 (6)	0.0132 (2)	0.000	0.000
O1	0.0367 (7)	0.0832 (14)	0.0448 (8)	0.0211 (8)	−0.0063 (6)	0.0004 (7)
O2	0.093 (3)	0.093 (3)	0.045 (3)	0.0464 (14)	0.000	0.000
O3	0.071 (3)	0.0472 (18)	0.109 (3)	0.028 (2)	0.015 (3)	0.0307 (17)
N1	0.0486 (9)	0.0486 (9)	0.0289 (10)	0.0243 (5)	0.000	0.000
C1	0.068 (3)	0.087 (4)	0.037 (2)	0.028 (3)	−0.026 (2)	0.003 (3)
C1A	0.060 (4)	0.058 (4)	0.032 (3)	0.022 (4)	−0.017 (3)	0.000 (3)
C2	0.040 (3)	0.077 (4)	0.047 (3)	0.014 (2)	−0.008 (2)	−0.0187 (19)
C2A	0.046 (4)	0.146 (12)	0.054 (5)	0.037 (6)	−0.025 (3)	0.008 (5)
C3	0.067 (4)	0.056 (3)	0.088 (4)	−0.007 (3)	−0.033 (3)	0.000 (3)
C3A	0.041 (4)	0.100 (7)	0.089 (6)	−0.005 (4)	0.009 (4)	−0.004 (5)

Geometric parameters (Å, º) top

Cl1—O2ⁱ	1.422 (4)	O3—O3ⁱ	1.533 (9)
Cl1—O2	1.422 (4)	O3—O3^v	1.797 (10)
Cl1—O3ⁱ	1.434 (3)	N1—C1	1.474 (4)
Cl1—O3ⁱⁱ	1.434 (3)	N1—C1^vi	1.474 (4)
Cl1—O3	1.434 (3)	N1—C1^viii	1.474 (4)
Cl1—O3ⁱⁱⁱ	1.434 (3)	N1—C1A^vi	1.480 (4)
Cl1—O3^iv	1.434 (3)	N1—C1A	1.480 (4)
Cl1—O3^v	1.434 (3)	N1—C1A^viii	1.480 (4)
Na1—O1	2.5661 (15)	C1—C2	1.473 (5)
Na1—O1^vi	2.5661 (15)	C1—H1A	0.9900
Na1—O1^vii	2.5661 (15)	C1—H1B	0.9900
Na1—O1^viii	2.5661 (15)	C1A—C2A	1.476 (6)
Na1—O1^ix	2.5661 (15)	C1A—H1C	0.9900
Na1—O1^x	2.5661 (15)	C1A—H1D	0.9900
Na1—N1	2.684 (2)	C2—H2A	0.9900
Na1—N1^ix	2.685 (2)	C2—H2B	0.9900
O1—C2	1.428 (4)	C2A—H2C	0.9900
O1—C2A	1.428 (4)	C2A—H2D	0.9900
O1—C3	1.436 (4)	C3—C3^ix	1.483 (6)
O1—C3A	1.425 (5)	C3—H3A	0.9900
O2—O3ⁱⁱⁱ	1.639 (5)	C3—H3B	0.9900
O2—O3^v	1.639 (5)	C3A—C3A^ix	1.474 (6)
O2—O3ⁱ	1.639 (5)	C3A—H3C	0.9900
O3—O2ⁱ	1.639 (5)	C3A—H3D	0.9900

O2ⁱ—Cl1—O2	180.000 (4)	C3—O1—Na1	112.2 (3)
O2ⁱ—Cl1—O3ⁱ	109.92 (16)	Cl1—O2—O3ⁱⁱⁱ	55.32 (15)
O2—Cl1—O3ⁱ	70.08 (16)	Cl1—O2—O3^v	55.32 (15)
O2ⁱ—Cl1—O3ⁱⁱ	70.08 (16)	O3ⁱⁱⁱ—O2—O3^v	90.8 (2)
O2—Cl1—O3ⁱⁱ	109.92 (16)	Cl1—O2—O3ⁱ	55.32 (15)
O3ⁱ—Cl1—O3ⁱⁱ	172.5 (5)	O3ⁱⁱⁱ—O2—O3ⁱ	90.8 (2)
O2ⁱ—Cl1—O3	70.08 (16)	O3^v—O2—O3ⁱ	90.8 (2)
O2—Cl1—O3	109.92 (16)	Cl1—O3—O3ⁱ	57.7 (2)
O3ⁱ—Cl1—O3	64.6 (5)	Cl1—O3—O2ⁱ	54.60 (16)
O3ⁱⁱ—Cl1—O3	109.01 (16)	O3ⁱ—O3—O2ⁱ	94.9 (4)
O2ⁱ—Cl1—O3ⁱⁱⁱ	109.92 (16)	Cl1—O3—O3^v	51.2 (2)
O2—Cl1—O3ⁱⁱⁱ	70.08 (16)	O3ⁱ—O3—O3^v	88.7 (3)
O3ⁱ—Cl1—O3ⁱⁱⁱ	109.01 (16)	O2ⁱ—O3—O3^v	85.6 (3)
O3ⁱⁱ—Cl1—O3ⁱⁱⁱ	77.6 (5)	C1—N1—C1^vi	113.1 (2)
O3—Cl1—O3ⁱⁱⁱ	172.5 (5)	C1—N1—C1^viii	113.1 (2)
O2ⁱ—Cl1—O3^iv	70.08 (16)	C1^vi—N1—C1^viii	113.1 (2)
O2—Cl1—O3^iv	109.92 (16)	C1A^vi—N1—C1A	108.0 (3)
O3ⁱ—Cl1—O3^iv	77.6 (5)	C1A^vi—N1—C1A^viii	108.0 (3)
O3ⁱⁱ—Cl1—O3^iv	109.01 (16)	C1A—N1—C1A^viii	108.0 (3)
O3—Cl1—O3^iv	109.01 (16)	C1—N1—Na1	105.5 (2)
O3ⁱⁱⁱ—Cl1—O3^iv	64.6 (4)	C1^vi—N1—Na1	105.5 (3)
O2ⁱ—Cl1—O3^v	109.92 (16)	C1^viii—N1—Na1	105.5 (2)
O2—Cl1—O3^v	70.08 (16)	C1A^vi—N1—Na1	110.9 (3)
O3ⁱ—Cl1—O3^v	109.01 (16)	C1A—N1—Na1	110.9 (3)
O3ⁱⁱ—Cl1—O3^v	64.6 (5)	C1A^viii—N1—Na1	110.9 (3)
O3—Cl1—O3^v	77.6 (5)	C2—C1—N1	116.1 (6)
O3ⁱⁱⁱ—Cl1—O3^v	109.01 (16)	C2—C1—H1A	108.3
O3^iv—Cl1—O3^v	172.5 (5)	N1—C1—H1A	108.3
O1—Na1—O1^vi	104.90 (3)	C2—C1—H1B	108.3
O1—Na1—O1^vii	167.11 (9)	N1—C1—H1B	108.3
O1^vi—Na1—O1^vii	86.11 (9)	H1A—C1—H1B	107.4
O1—Na1—O1^viii	104.90 (3)	C2A—C1A—N1	107.4 (8)
O1^vi—Na1—O1^viii	104.90 (3)	C2A—C1A—H1C	110.2
O1^vii—Na1—O1^viii	65.09 (7)	N1—C1A—H1C	110.2
O1—Na1—O1^ix	65.09 (7)	C2A—C1A—H1D	110.2
O1^vi—Na1—O1^ix	167.11 (9)	N1—C1A—H1D	110.2
O1^vii—Na1—O1^ix	104.90 (3)	H1C—C1A—H1D	108.5
O1^viii—Na1—O1^ix	86.11 (9)	O1—C2—C1	109.0 (4)
O1—Na1—O1^x	86.11 (9)	O1—C2—H2A	109.9
O1^vi—Na1—O1^x	65.09 (7)	C1—C2—H2A	109.9
O1^vii—Na1—O1^x	104.89 (3)	O1—C2—H2B	109.9
O1^viii—Na1—O1^x	167.11 (9)	C1—C2—H2B	109.9
O1^ix—Na1—O1^x	104.89 (3)	H2A—C2—H2B	108.3
O1—Na1—N1	66.27 (3)	O1—C2A—C1A	112.6 (7)
O1^vi—Na1—N1	66.27 (3)	O1—C2A—H2C	109.1
O1^vii—Na1—N1	113.73 (3)	C1A—C2A—H2C	109.1
O1^viii—Na1—N1	66.27 (3)	O1—C2A—H2D	109.1
O1^ix—Na1—N1	113.73 (3)	C1A—C2A—H2D	109.1
O1^x—Na1—N1	113.73 (3)	H2C—C2A—H2D	107.8
O1—Na1—N1^ix	113.73 (3)	O1—C3—C3^ix	105.9 (4)
O1^vi—Na1—N1^ix	113.73 (3)	O1—C3—H3A	110.5
O1^vii—Na1—N1^ix	66.27 (3)	C3^ix—C3—H3A	110.5
O1^viii—Na1—N1^ix	113.73 (3)	O1—C3—H3B	110.5
O1^ix—Na1—N1^ix	66.27 (3)	C3^ix—C3—H3B	110.5
O1^x—Na1—N1^ix	66.27 (3)	H3A—C3—H3B	108.7
N1—Na1—N1^ix	180.0	O1—C3A—C3A^ix	106.5 (5)
C3A—O1—C2A	135.9 (9)	O1—C3A—H3C	110.4
C2—O1—C3	96.9 (4)	C3A^ix—C3A—H3C	110.4
C3A—O1—Na1	112.0 (4)	O1—C3A—H3D	110.4
C2A—O1—Na1	111.3 (6)	C3A^ix—C3A—H3D	110.4
C2—O1—Na1	119.3 (3)	H3C—C3A—H3D	108.6

O3ⁱ—Cl1—O2—O3ⁱⁱⁱ	120.000 (5)	O1^x—Na1—O1—C3	126.9 (3)
O3ⁱⁱ—Cl1—O2—O3ⁱⁱⁱ	−68.0 (5)	N1—Na1—O1—C3	−115.1 (3)
O3—Cl1—O2—O3ⁱⁱⁱ	172.0 (5)	N1^ix—Na1—O1—C3	64.9 (3)
O3^iv—Cl1—O2—O3ⁱⁱⁱ	52.0 (5)	O1—Na1—N1—C1	−23.0 (4)
O3^v—Cl1—O2—O3ⁱⁱⁱ	−120.000 (5)	O1^vi—Na1—N1—C1	97.0 (4)
O3ⁱ—Cl1—O2—O3^v	−120.000 (14)	O1^vii—Na1—N1—C1	171.1 (3)
O3ⁱⁱ—Cl1—O2—O3^v	52.0 (5)	O1^viii—Na1—N1—C1	−143.0 (4)
O3—Cl1—O2—O3^v	−68.0 (5)	O1^ix—Na1—N1—C1	−68.9 (3)
O3ⁱⁱⁱ—Cl1—O2—O3^v	120.000 (13)	O1^x—Na1—N1—C1	51.1 (3)
O3^iv—Cl1—O2—O3^v	172.0 (5)	O1—Na1—N1—C1^vi	−143.0 (3)
O3ⁱⁱ—Cl1—O2—O3ⁱ	172.0 (5)	O1^vi—Na1—N1—C1^vi	−23.0 (3)
O3—Cl1—O2—O3ⁱ	52.0 (5)	O1^vii—Na1—N1—C1^vi	51.1 (3)
O3ⁱⁱⁱ—Cl1—O2—O3ⁱ	−120.000 (3)	O1^viii—Na1—N1—C1^vi	97.0 (3)
O3^iv—Cl1—O2—O3ⁱ	−68.0 (5)	O1^ix—Na1—N1—C1^vi	171.1 (3)
O3^v—Cl1—O2—O3ⁱ	120.000 (2)	O1^x—Na1—N1—C1^vi	−68.9 (3)
O2ⁱ—Cl1—O3—O3ⁱ	125.0 (4)	O1—Na1—N1—C1^viii	97.0 (4)
O2—Cl1—O3—O3ⁱ	−55.0 (4)	O1^vi—Na1—N1—C1^viii	−143.0 (4)
O3ⁱⁱ—Cl1—O3—O3ⁱ	−175.6 (3)	O1^vii—Na1—N1—C1^viii	−68.9 (4)
O3^iv—Cl1—O3—O3ⁱ	65.5 (5)	O1^viii—Na1—N1—C1^viii	−23.0 (4)
O3^v—Cl1—O3—O3ⁱ	−118.2 (4)	O1^ix—Na1—N1—C1^viii	51.1 (4)
O2—Cl1—O3—O2ⁱ	180.000 (4)	O1^x—Na1—N1—C1^viii	171.1 (4)
O3ⁱ—Cl1—O3—O2ⁱ	−125.0 (4)	O1—Na1—N1—C1A^vi	−107.5 (4)
O3ⁱⁱ—Cl1—O3—O2ⁱ	59.45 (19)	O1^vi—Na1—N1—C1A^vi	12.5 (4)
O3^iv—Cl1—O3—O2ⁱ	−59.45 (19)	O1^vii—Na1—N1—C1A^vi	86.6 (4)
O3^v—Cl1—O3—O2ⁱ	116.8 (3)	O1^viii—Na1—N1—C1A^vi	132.5 (4)
O2ⁱ—Cl1—O3—O3^v	−116.8 (3)	O1^ix—Na1—N1—C1A^vi	−153.4 (4)
O2—Cl1—O3—O3^v	63.2 (3)	O1^x—Na1—N1—C1A^vi	−33.4 (4)
O3ⁱ—Cl1—O3—O3^v	118.2 (4)	O1—Na1—N1—C1A	12.5 (4)
O3ⁱⁱ—Cl1—O3—O3^v	−57.3 (4)	O1^vi—Na1—N1—C1A	132.5 (4)
O3^iv—Cl1—O3—O3^v	−176.2 (2)	O1^vii—Na1—N1—C1A	−153.4 (4)
O1^vi—Na1—O1—C3A	153.1 (4)	O1^viii—Na1—N1—C1A	−107.5 (4)
O1^vii—Na1—O1—C3A	−58.9 (4)	O1^ix—Na1—N1—C1A	−33.4 (4)
O1^viii—Na1—O1—C3A	−96.7 (4)	O1^x—Na1—N1—C1A	86.6 (4)
O1^ix—Na1—O1—C3A	−18.3 (4)	O1—Na1—N1—C1A^viii	132.5 (5)
O1^x—Na1—O1—C3A	90.1 (4)	O1^vi—Na1—N1—C1A^viii	−107.5 (5)
N1—Na1—O1—C3A	−151.8 (4)	O1^vii—Na1—N1—C1A^viii	−33.4 (4)
N1^ix—Na1—O1—C3A	28.2 (4)	O1^viii—Na1—N1—C1A^viii	12.5 (5)
O1^vi—Na1—O1—C2A	−35.5 (7)	O1^ix—Na1—N1—C1A^viii	86.6 (5)
O1^vii—Na1—O1—C2A	112.5 (7)	O1^x—Na1—N1—C1A^viii	−153.4 (5)
O1^viii—Na1—O1—C2A	74.8 (7)	C3—O1—C2—C1	149.0 (7)
O1^ix—Na1—O1—C2A	153.2 (7)	Na1—O1—C2—C1	28.7 (9)
O1^x—Na1—O1—C2A	−98.4 (7)	C3A—O1—C2A—C1A	115.5 (10)
N1—Na1—O1—C2A	19.7 (7)	Na1—O1—C2A—C1A	−53.0 (13)
N1^ix—Na1—O1—C2A	−160.3 (7)	C2—O1—C3—C3^ix	−177.7 (7)
O1^vi—Na1—O1—C2	−58.0 (5)	Na1—O1—C3—C3^ix	−52.1 (8)
O1^vii—Na1—O1—C2	90.0 (5)	C2A—O1—C3A—C3A^ix	−116.9 (11)
O1^viii—Na1—O1—C2	52.3 (5)	Na1—O1—C3A—C3A^ix	51.6 (10)
O1^ix—Na1—O1—C2	130.7 (5)	C1^vi—N1—C1—C2	166.0 (5)
O1^x—Na1—O1—C2	−120.9 (5)	C1^viii—N1—C1—C2	−63.7 (9)
N1—Na1—O1—C2	−2.8 (5)	Na1—N1—C1—C2	51.2 (6)
N1^ix—Na1—O1—C2	177.2 (5)	C1A^vi—N1—C1A—C2A	79.9 (10)
O1^vi—Na1—O1—C3	−170.2 (3)	C1A^viii—N1—C1A—C2A	−163.5 (7)
O1^vii—Na1—O1—C3	−22.2 (3)	Na1—N1—C1A—C2A	−41.8 (8)
O1^viii—Na1—O1—C3	−59.9 (3)	N1—C1—C2—O1	−55.6 (9)
O1^ix—Na1—O1—C3	18.5 (3)	N1—C1A—C2A—O1	65.1 (14)

Symmetry codes: (i) y, x, −z+2; (ii) −y+2, x−y+1, z; (iii) x−y+1, −y+2, −z+2; (iv) −x+y+1, −x+2, z; (v) −x+2, −x+y+1, −z+2; (vi) −x+y+1, −x+1, z; (vii) −x+4/3, −x+y+2/3, −z+5/3; (viii) −y+1, x−y, z; (ix) y+1/3, x−1/3, −z+5/3; (x) x−y+1/3, −y+2/3, −z+5/3.

Experimental details

Crystal data
Chemical formula	[Na(C₁₈H₃₆N₂O₆)]ClO₄
M_r	498.93
Crystal system, space group	Rhombohedral, R32
Temperature (K)	100
a, c (Å)	8.4730 (3), 28.220 (3)
V (Å³)	1754.5 (2)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.49 × 0.37 × 0.35

Data collection
Diffractometer	Bruker CCD-1000 area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.893, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	6885, 805, 765
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.113, 1.11
No. of reflections	805
No. of parameters	85
No. of restraints	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.18
Absolute structure	Flack (1983), 319 Friedel pairs
Absolute structure parameter	0.01 (15)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg, 1999), modiCIFer (Guzei, 2007) and publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

Cl1—O2ⁱ	1.422 (4)	Cl1—O3^iv	1.434 (3)
Cl1—O2	1.422 (4)	Cl1—O3^v	1.434 (3)
Cl1—O3ⁱ	1.434 (3)	Na1—O1	2.5661 (15)
Cl1—O3ⁱⁱ	1.434 (3)	Na1—N1	2.684 (2)
Cl1—O3	1.434 (3)	O2—O3ⁱⁱⁱ	1.639 (5)
Cl1—O3ⁱⁱⁱ	1.434 (3)	O3—O3^v	1.797 (10)

O2ⁱ—Cl1—O2	180.000 (4)	O3—Cl1—O3ⁱⁱⁱ	172.5 (5)
O2ⁱ—Cl1—O3ⁱ	109.92 (16)	O2ⁱ—Cl1—O3^iv	70.08 (16)
O2—Cl1—O3ⁱ	70.08 (16)	O2—Cl1—O3^iv	109.92 (16)
O2ⁱ—Cl1—O3ⁱⁱ	70.08 (16)	O3ⁱ—Cl1—O3^iv	77.6 (5)
O2—Cl1—O3ⁱⁱ	109.92 (16)	O3ⁱⁱ—Cl1—O3^iv	109.01 (16)
O3ⁱ—Cl1—O3ⁱⁱ	172.5 (5)	O3—Cl1—O3^iv	109.01 (16)
O2ⁱ—Cl1—O3	70.08 (16)	O3ⁱⁱⁱ—Cl1—O3^iv	64.6 (4)
O2—Cl1—O3	109.92 (16)	O2ⁱ—Cl1—O3^v	109.92 (16)
O3ⁱ—Cl1—O3	64.6 (5)	O2—Cl1—O3^v	70.08 (16)
O3ⁱⁱ—Cl1—O3	109.01 (16)	O3ⁱ—Cl1—O3^v	109.01 (16)
O2ⁱ—Cl1—O3ⁱⁱⁱ	109.92 (16)	O3ⁱⁱ—Cl1—O3^v	64.6 (5)
O2—Cl1—O3ⁱⁱⁱ	70.08 (16)	O3—Cl1—O3^v	77.6 (5)
O3ⁱ—Cl1—O3ⁱⁱⁱ	109.01 (16)	O3ⁱⁱⁱ—Cl1—O3^v	109.01 (16)
O3ⁱⁱ—Cl1—O3ⁱⁱⁱ	77.6 (5)	O3^iv—Cl1—O3^v	172.5 (5)

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

Acknowledgements

We thank the National Science Foundation for financial support.

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