(1,4,7,10-Tetra­oxacyclo­dodeca­ne)(trideuteroacetonitrile)lithium perchlorate

Guzei, I.A.; Spencer, L.C.; Xiao, L.; Burnette, R.R.

doi:10.1107/S1600536810009530

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m440-m441

doi:10.1107/S1600536810009530

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(1,4,7,10-Tetraoxacyclododecane)(trideuteroacetonitrile)lithium perchlorate

Ilia A. Guzei,^a ^* Lara C. Spencer,^a Lingyun Xiao ^b and Ronald R. Burnette ^c

^aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA, ^bSmall Molecule Process & Product Development, AMGEN, One Amgen Center Drive, Thousand Oaks, CA 91320, USA, and ^cSchool of Pharmacy, University of Wisconsin-Madison, 777 Highland Ave, Madison, WI 53705, USA
^*Correspondence e-mail: iguzei@chem.wisc.edu

(Received 4 March 2010; accepted 12 March 2010; online 24 March 2010)

In the title compound, [Li(C₈H₁₆O₄)(CD₃CN)]ClO₄, the Li atom is pentacoordinate. The O atoms of the 12-crown-4 ether form the basal plane, whereas the N atom of the trideuteroacetonitrile occupies the apical position. The Li⁺ atom is displaced by 0.794 (6) Å toward the apical position from the plane formed by the O atoms because the Li⁺ atom is too large to fit in the cavity of the 12-crown-4 ether, resulting in a distorted square-pyramidal geometry about the Li⁺ atom.

Related literature

For applications of crown ethers, see: Jagannadh & Sarma (1999 ); Lehn (1973 , 1995 ); Doyle & McCord (1998 ); Blasius et al. (1982 ); Blasius & Janzen (1982 ); Hayashita et al. (1992 ); Frühauf & Zeller (1991 ). For 12-crown-4 ether geometry, see: Raithby et al. (1997 ); Jones et al. (1997 ). For the size of the crown ether cavity and lithium ion, see: Shoham et al. (1983 ); Dalley (1978 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2002 ). For a description of tris(1,4,7,10-tetraoxacyclododecane)dilithium bis(perchlorate), synthesized simultaneously with the title compound, see: Guzei et al. (2010 ).

Experimental

Crystal data

[Li(C₈H₁₆O₄)(C₂D₃N)]ClO₄
M_r = 323.65
Orthorhombic, P b c a
a = 12.1605 (14) Å
b = 12.6338 (15) Å
c = 19.870 (2) Å
V = 3052.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker CCD-1000 area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.895, T_max = 0.945
20941 measured reflections
2621 independent reflections
2164 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.214
S = 1.03
2621 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Selected bond lengths (Å)

O1—Li1	2.022 (6)
O2—Li1	2.058 (6)
O3—Li1	2.036 (6)
O4—Li1	2.050 (6)
N1—Li1	2.010 (6)

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL and FCF_filter (Guzei, 2007 ); molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010 ) and modiCIFer (Guzei, 2007).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009530/si2247sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009530/si2247Isup2.hkl

checkCIF report

Comment top

Crown ethers are important due to their remarkable selectivity toward complexation with metal ions through oxygen atoms on the crown ether ring. They have high conformational flexibility, act as host molecules for various guests (Jagannadh et al., 1999), and have a broad range of applications. Their importance has been studied in numerous fields such as molecular design (Lehn, 1973), supramolecular chemistry (Lehn, 1995), analytical chemistry (Doyle & McCord, 1998; Blasius et al., 1982; Blasius & Janzen, 1982; Hayashita et al., 1992) and medicine (Frühauf & Zeller, 1991). The ionic title compound (I), a crown ether/Li⁺ system, was prepared in a study aiming to develop a systematic methodology to understand the nature of these complexes. This methodology based on experimental crystallography may find application in characterization of host-guest type drug delivery systems.

Compound (I) crystallizes with discrete cations and anions. The Li⁺ atom of the cation exhibits a distorted square pyramidal geometry. The four oxygen atoms of the 12-crown-4 ether (12C4) bond to lithium in the basal positions, and the acetonitrile nitrogen atom occupies the apical position. The 12C4 is in the frequently observed [3333] conformation approximating C₄ symmetry (Raithby et al., 1997; Jones et al., 1997). The oxygen atoms are nearly planar with a rms of 0.1325 (14) Å. The lithium atom is displaced out of this plane toward the apical position by 0.794 (6) Å. This displacement results from the Li⁺ being too large to fit in the cavity of the crown ether. The two diagonal distances across the ring between the opposite oxygens are 3.611 (4) Å and 3.890 (4) Å resulting in an adjusted diameter of the cavity between 0.811 Å and 1.090 Å. This cavity is too small to accomodate the lithium ion whose ionic diameter is between 1.18 Å and 1.52 Å (Shoham et al., 1983; Dalley, 1978). The Li—N vector is nearly perpendicular to the plane of the 12C4 oxygen atoms forming a 89.8 (5)° angle. The angles and distances involving lithium were statistically similar to the averages for 14 related compounds found in the Cambridge Structural Database (CSD; Version 1.11, September 2009 release; Allen, 2002). A Mogul structural check also confirmed that (I) exhibits typical geometrical parameters (Bruno et al., 2002).

The lithium complexes and the perchorate anions in the lattice of (I) are each stacked along a twofold screw axis to form columns along the a axis.

Related literature top

For applications of crown ethers, see: Jagannadh et al. (1999); Lehn (1973, (1995); Doyle & McCord (1998); Blasius et al. (1982); Blasius & Janzen (1982); Hayashita et al. (1992); Frühauf & Zeller (1991). For 12-crown-4 ether geometry, see: Raithby et al. (1997); Jones et al. (1997). For the size of the crown ether cavity and lithium ion, see: Shoham et al. (1983); Dalley (1978). For a description of the Cambridge Structural Database, see: Allen (2002). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2002). For a description of tris(1,4,7,10-tetraoxacyclododecane)-di-lithium perchlorate synthesized simultaneously with the title compound, see: Guzei et al. (2010).

Experimental top

All chemicals were purchased from the Aldrich Chemical Co. Inc. and were used as received. 12-crown-4 (12C4, C₈H₁₆O₄, 98% pure) and lithium perchlorate (LiClO₄, 99% pure) were separately dissolved in acetonitrile-d₃ (CD₃CN, 99% pure). These two solutions were then mixed together according to a 1:1 molar ratio of 12C4/LiClO₄.The final solution was kept in a desiccator and the solvent was allowed to evaporate gradually in order to produce a supersaturated solution. The supersaturated solution was stored at –20 °C refrigerator, until crystals formed after 48 hours. Two types of colorless crystals suitable for X-ray diffraction were obtained and separated from the solution, one of which was compound (I) the other being tris(1,4,7,10-tetraoxacyclododecane)-di-lithium diperchlorate (Guzei et al., 2010).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008) and FCF_filter (Guzei, 2007); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and modiCIFer (Guzei, 2007).

Figures top

Fig. 1. Molecular structure of (I). The thermal ellipsoids are shown at 50% probability level. All hydrogen atoms were omitted for clarity.

(1,4,7,10-Tetraoxacyclododecane)(trideuteroacetonitrile)lithium perchlorate top

Crystal data top

[Li(C₈H₁₆O₄)(C₂D₃N)]ClO₄	F(000) = 1360
M_r = 323.65	D_x = 1.408 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 999 reflections
a = 12.1605 (14) Å	θ = 2.5–24.8°
b = 12.6338 (15) Å	µ = 0.29 mm⁻¹
c = 19.870 (2) Å	T = 100 K
V = 3052.7 (6) Å³	Block, colourless
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker CCD-1000 area-detector diffractometer	2621 independent reflections
Radiation source: fine-focus sealed tube	2164 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
0.30° ω and 0.4 ° ϕ scans	θ_max = 24.8°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
T_min = 0.895, T_max = 0.945	k = −14→14
20941 measured reflections	l = −23→23

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1041P)² + 6.1747P] where P = (F_o² + 2F_c²)/3
2621 reflections	(Δ/σ)_max = 0.024
191 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Li(C₈H₁₆O₄)(C₂D₃N)]ClO₄	V = 3052.7 (6) Å³
M_r = 323.65	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.1605 (14) Å	µ = 0.29 mm⁻¹
b = 12.6338 (15) Å	T = 100 K
c = 19.870 (2) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker CCD-1000 area-detector diffractometer	2621 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2164 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.945	R_int = 0.030
20941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 1.03	Δρ_max = 0.81 e Å⁻³
2621 reflections	Δρ_min = −0.36 e Å⁻³
191 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 > 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
Cl1	0.13806 (7)	0.22119 (7)	0.03636 (4)	0.0480 (3)
O1	0.0293 (2)	0.1535 (2)	0.28852 (16)	0.0647 (8)
O2	0.2455 (2)	0.1542 (2)	0.27072 (15)	0.0672 (8)
O3	0.2453 (2)	−0.0130 (3)	0.35435 (13)	0.0637 (8)
O4	0.0258 (2)	−0.0332 (2)	0.34845 (13)	0.0627 (8)
O5	0.2322 (3)	0.1706 (3)	0.06187 (18)	0.0885 (11)
O6	0.1349 (3)	0.2031 (4)	−0.03414 (17)	0.1030 (15)
O7	0.1441 (3)	0.3323 (3)	0.0458 (3)	0.1151 (17)
O8	0.0413 (3)	0.1795 (3)	0.06594 (17)	0.0792 (10)
N1	0.1324 (2)	−0.0384 (3)	0.19108 (15)	0.0479 (8)
Li1	0.1361 (4)	0.0312 (5)	0.2820 (3)	0.0427 (13)
C1	0.0820 (5)	0.2547 (4)	0.2874 (3)	0.0878 (17)
H1A	0.0332	0.3078	0.2662	0.105*
H1B	0.0984	0.2782	0.3339	0.105*
C2	0.1800 (5)	0.2452 (4)	0.2504 (4)	0.0945 (18)
H2A	0.2242	0.3103	0.2563	0.113*
H2B	0.1618	0.2387	0.2020	0.113*
C3	0.3096 (4)	0.1645 (5)	0.3295 (3)	0.0889 (18)
H3A	0.2669	0.2001	0.3654	0.107*
H3B	0.3765	0.2068	0.3203	0.107*
C4	0.3396 (4)	0.0557 (6)	0.3504 (3)	0.0899 (19)
H4A	0.3927	0.0261	0.3176	0.108*
H4B	0.3760	0.0584	0.3949	0.108*
C5	0.1849 (5)	−0.0045 (5)	0.4155 (2)	0.0873 (17)
H5A	0.2286	−0.0337	0.4532	0.105*
H5B	0.1688	0.0707	0.4253	0.105*
C6	0.0857 (5)	−0.0617 (5)	0.4086 (2)	0.0805 (15)
H6A	0.0387	−0.0483	0.4484	0.097*
H6B	0.1024	−0.1384	0.4073	0.097*
C7	−0.0691 (4)	0.0308 (5)	0.3513 (3)	0.0782 (14)
H7A	−0.1077	0.0182	0.3944	0.094*
H7B	−0.1195	0.0107	0.3143	0.094*
C8	−0.0425 (4)	0.1423 (4)	0.3456 (2)	0.0767 (14)
H8A	−0.1103	0.1844	0.3389	0.092*
H8B	−0.0055	0.1673	0.3870	0.092*
C9	0.1229 (3)	−0.0579 (3)	0.13610 (17)	0.0405 (8)
C10	0.1084 (4)	−0.0830 (4)	0.06532 (18)	0.0582 (10)
D10A	0.0403	−0.1235	0.0594	0.087*
D10B	0.1709	−0.1251	0.0496	0.087*
D10C	0.1040	−0.0173	0.0392	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0511 (6)	0.0499 (6)	0.0430 (6)	−0.0013 (4)	0.0001 (4)	0.0025 (4)
O1	0.0504 (16)	0.0519 (16)	0.092 (2)	0.0035 (12)	0.0154 (15)	0.0002 (15)
O2	0.0497 (15)	0.0672 (18)	0.085 (2)	−0.0098 (13)	0.0005 (15)	−0.0171 (15)
O3	0.0570 (17)	0.089 (2)	0.0449 (14)	0.0253 (15)	−0.0082 (12)	−0.0116 (14)
O4	0.0598 (17)	0.082 (2)	0.0460 (15)	−0.0077 (15)	0.0056 (13)	0.0086 (13)
O5	0.071 (2)	0.102 (3)	0.093 (2)	0.0072 (19)	−0.0286 (19)	0.019 (2)
O6	0.089 (3)	0.175 (5)	0.0449 (19)	0.010 (3)	−0.0026 (16)	−0.001 (2)
O7	0.095 (3)	0.057 (2)	0.193 (5)	−0.0080 (19)	0.038 (3)	−0.019 (3)
O8	0.072 (2)	0.091 (2)	0.075 (2)	−0.0203 (18)	0.0178 (16)	0.0094 (18)
N1	0.0537 (18)	0.0506 (18)	0.0395 (17)	−0.0010 (13)	0.0001 (13)	−0.0062 (13)
Li1	0.044 (3)	0.049 (3)	0.034 (3)	0.002 (2)	−0.002 (2)	−0.007 (2)
C1	0.082 (4)	0.054 (3)	0.128 (5)	0.010 (3)	0.006 (3)	0.013 (3)
C2	0.103 (4)	0.060 (3)	0.121 (5)	−0.015 (3)	0.030 (4)	0.010 (3)
C3	0.059 (3)	0.114 (5)	0.093 (4)	−0.029 (3)	0.004 (3)	−0.044 (3)
C4	0.045 (2)	0.143 (6)	0.081 (3)	0.017 (3)	−0.021 (2)	−0.037 (4)
C5	0.089 (4)	0.130 (5)	0.043 (2)	0.027 (4)	−0.006 (2)	0.000 (3)
C6	0.106 (4)	0.088 (4)	0.047 (2)	−0.012 (3)	0.002 (3)	0.013 (2)
C7	0.057 (3)	0.111 (4)	0.067 (3)	−0.014 (3)	0.012 (2)	0.001 (3)
C8	0.054 (3)	0.099 (4)	0.077 (3)	0.020 (3)	0.017 (2)	−0.017 (3)
C9	0.0419 (18)	0.0396 (18)	0.0401 (19)	0.0004 (14)	−0.0002 (14)	−0.0042 (14)
C10	0.075 (3)	0.064 (2)	0.0359 (19)	0.005 (2)	−0.0047 (18)	−0.0088 (17)

Geometric parameters (Å, º) top

Cl1—O5	1.406 (3)	C2—H2A	0.9900
Cl1—O8	1.416 (3)	C2—H2B	0.9900
Cl1—O7	1.418 (4)	C3—C4	1.481 (9)
Cl1—O6	1.420 (4)	C3—H3A	0.9900
O1—C1	1.430 (6)	C3—H3B	0.9900
O1—C8	1.439 (5)	C4—H4A	0.9900
O1—Li1	2.022 (6)	C4—H4B	0.9900
O2—C3	1.411 (6)	C5—C6	1.413 (8)
O2—C2	1.456 (7)	C5—H5A	0.9900
O2—Li1	2.058 (6)	C5—H5B	0.9900
O3—C5	1.424 (5)	C6—H6A	0.9900
O3—C4	1.440 (7)	C6—H6B	0.9900
O3—Li1	2.036 (6)	C7—C8	1.449 (7)
O4—C7	1.411 (6)	C7—H7A	0.9900
O4—C6	1.444 (6)	C7—H7B	0.9900
O4—Li1	2.050 (6)	C8—H8A	0.9900
N1—C9	1.126 (4)	C8—H8B	0.9900
N1—Li1	2.010 (6)	C9—C10	1.452 (5)
C1—C2	1.405 (8)	C10—D10A	0.9800
C1—H1A	0.9900	C10—D10B	0.9800
C1—H1B	0.9900	C10—D10C	0.9800

O5—Cl1—O8	111.0 (2)	O2—C3—H3A	110.5
O5—Cl1—O7	111.1 (3)	C4—C3—H3A	110.5
O8—Cl1—O7	110.9 (2)	O2—C3—H3B	110.5
O5—Cl1—O6	107.7 (2)	C4—C3—H3B	110.5
O8—Cl1—O6	109.1 (2)	H3A—C3—H3B	108.7
O7—Cl1—O6	106.9 (3)	O3—C4—C3	112.3 (4)
C1—O1—C8	111.9 (4)	O3—C4—H4A	109.2
C1—O1—Li1	113.2 (3)	C3—C4—H4A	109.2
C8—O1—Li1	111.4 (3)	O3—C4—H4B	109.2
C3—O2—C2	117.3 (4)	C3—C4—H4B	109.2
C3—O2—Li1	109.7 (3)	H4A—C4—H4B	107.9
C2—O2—Li1	105.8 (3)	C6—C5—O3	108.6 (4)
C5—O3—C4	114.3 (4)	C6—C5—H5A	110.0
C5—O3—Li1	104.2 (3)	O3—C5—H5A	110.0
C4—O3—Li1	108.4 (3)	C6—C5—H5B	110.0
C7—O4—C6	121.5 (4)	O3—C5—H5B	110.0
C7—O4—Li1	109.4 (3)	H5A—C5—H5B	108.4
C6—O4—Li1	107.6 (3)	C5—C6—O4	112.5 (4)
C9—N1—Li1	166.0 (4)	C5—C6—H6A	109.1
N1—Li1—O1	112.2 (3)	O4—C6—H6A	109.1
N1—Li1—O3	121.9 (3)	C5—C6—H6B	109.1
O1—Li1—O3	125.7 (3)	O4—C6—H6B	109.1
N1—Li1—O4	113.0 (3)	H6A—C6—H6B	107.8
O1—Li1—O4	80.9 (2)	O4—C7—C8	111.8 (4)
O3—Li1—O4	82.1 (2)	O4—C7—H7A	109.2
N1—Li1—O2	104.3 (3)	C8—C7—H7A	109.2
O1—Li1—O2	81.1 (2)	O4—C7—H7B	109.2
O3—Li1—O2	82.1 (2)	C8—C7—H7B	109.2
O4—Li1—O2	142.4 (3)	H7A—C7—H7B	107.9
C2—C1—O1	108.1 (4)	O1—C8—C7	107.0 (4)
C2—C1—H1A	110.1	O1—C8—H8A	110.3
O1—C1—H1A	110.1	C7—C8—H8A	110.3
C2—C1—H1B	110.1	O1—C8—H8B	110.3
O1—C1—H1B	110.1	C7—C8—H8B	110.3
H1A—C1—H1B	108.4	H8A—C8—H8B	108.6
C1—C2—O2	112.8 (4)	N1—C9—C10	178.9 (4)
C1—C2—H2A	109.0	C9—C10—D10A	109.5
O2—C2—H2A	109.0	C9—C10—D10B	109.5
C1—C2—H2B	109.0	D10A—C10—D10B	109.5
O2—C2—H2B	109.0	C9—C10—D10C	109.5
H2A—C2—H2B	107.8	D10A—C10—D10C	109.5
O2—C3—C4	106.3 (4)	D10B—C10—D10C	109.5

C9—N1—Li1—O1	25.1 (15)	C2—O2—Li1—N1	91.0 (4)
C9—N1—Li1—O3	−150.4 (12)	C3—O2—Li1—O1	107.7 (3)
C9—N1—Li1—O4	114.5 (13)	C2—O2—Li1—O1	−19.7 (4)
C9—N1—Li1—O2	−60.9 (14)	C3—O2—Li1—O3	−20.5 (4)
C1—O1—Li1—N1	−106.3 (4)	C2—O2—Li1—O3	−147.9 (3)
C8—O1—Li1—N1	126.6 (4)	C3—O2—Li1—O4	45.4 (6)
C1—O1—Li1—O3	69.1 (5)	C2—O2—Li1—O4	−82.0 (6)
C8—O1—Li1—O3	−58.0 (5)	C8—O1—C1—C2	155.6 (5)
C1—O1—Li1—O4	142.5 (4)	Li1—O1—C1—C2	28.7 (6)
C8—O1—Li1—O4	15.4 (3)	O1—C1—C2—O2	−48.1 (7)
C1—O1—Li1—O2	−4.4 (4)	C3—O2—C2—C1	−79.4 (6)
C8—O1—Li1—O2	−131.5 (3)	Li1—O2—C2—C1	43.3 (6)
C5—O3—Li1—N1	−143.2 (4)	C2—O2—C3—C4	163.1 (4)
C4—O3—Li1—N1	94.7 (4)	Li1—O2—C3—C4	42.5 (5)
C5—O3—Li1—O1	41.8 (5)	C5—O3—C4—C3	−82.2 (5)
C4—O3—Li1—O1	−80.3 (4)	Li1—O3—C4—C3	33.5 (5)
C5—O3—Li1—O4	−31.0 (4)	O2—C3—C4—O3	−51.2 (6)
C4—O3—Li1—O4	−153.1 (3)	C4—O3—C5—C6	170.3 (5)
C5—O3—Li1—O2	114.8 (4)	Li1—O3—C5—C6	52.2 (5)
C4—O3—Li1—O2	−7.3 (3)	O3—C5—C6—O4	−51.1 (6)
C7—O4—Li1—N1	−99.2 (4)	C7—O4—C6—C5	−104.8 (5)
C6—O4—Li1—N1	126.9 (4)	Li1—O4—C6—C5	22.3 (6)
C7—O4—Li1—O1	11.2 (3)	C6—O4—C7—C8	90.0 (5)
C6—O4—Li1—O1	−122.7 (3)	Li1—O4—C7—C8	−36.3 (5)
C7—O4—Li1—O3	139.4 (3)	C1—O1—C8—C7	−165.9 (4)
C6—O4—Li1—O3	5.5 (4)	Li1—O1—C8—C7	−38.0 (5)
C7—O4—Li1—O2	73.5 (6)	O4—C7—C8—O1	49.2 (5)
C6—O4—Li1—O2	−60.4 (6)	Li1—N1—C9—C10	−72 (20)
C3—O2—Li1—N1	−141.5 (4)

Experimental details

Crystal data
Chemical formula	[Li(C₈H₁₆O₄)(C₂D₃N)]ClO₄
M_r	323.65
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	12.1605 (14), 12.6338 (15), 19.870 (2)
V (Å³)	3052.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker CCD-1000 area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.895, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	20941, 2621, 2164
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.590

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.214, 1.03
No. of reflections	2621
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.36

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008) and FCF_filter (Guzei, 2007), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and modiCIFer (Guzei, 2007).

Selected bond lengths (Å) top

O1—Li1	2.022 (6)	O4—Li1	2.050 (6)
O2—Li1	2.058 (6)	N1—Li1	2.010 (6)
O3—Li1	2.036 (6)

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blasius, E. & Janzen, K. P. (1982). Pure Appl. Chem. 54, 2115–2128. CrossRef CAS Web of Science Google Scholar
Blasius, E., Janzen, K. P., Klotz, H. & Toussaint, A. (1982). Makromol. Chem. 183, 1401–1411. CrossRef CAS Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2003). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dalley, N. D. (1978). Synthetic Multidentate Macrocyclic Compounds, edited by R. M. Izatt & J. J. Christensen, pp. 207–243. New York: Academic Press. Google Scholar
Doyle, J. M. & McCord, B. R. (1998). J. Chromatogr. B, 714, 105–111. CrossRef CAS Google Scholar
Frühauf, S. & Zeller, W. J. (1991). Cancer Res. 51, 2943–2948. PubMed Web of Science Google Scholar
Guzei, I. A. (2007). FCF_filter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA. Google Scholar
Guzei, I. A., Spencer, L. C., Xiao, L. & Burnette, R. R. (2010). Acta Cryst. E66, m438–m439. Web of Science CrossRef IUCr Journals Google Scholar
Hayashita, T., Lee, J. H., Hankins, M. G., Lee, J. C., Kim, J. S., Knobeloch, J. M. & Bartsch, R. A. (1992). Anal. Chem. 64, 815–819. CrossRef CAS Web of Science Google Scholar
Jagannadh, B. & Sarma, J. A. R. P. (1999). J. Phys. Chem. A, 103, 10993–10997. Web of Science CrossRef CAS Google Scholar
Jones, P. G., Moers, O. & Blaschette, A. (1997). Acta Cryst. C53, 1809–1811. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Lehn, J. M. (1973). Struct. Bond. 16, 1–69. CrossRef CAS Google Scholar
Lehn, J. M. (1995). Supramolecular Chemistry: Concepts and Perspectives. Weinheim, VCH. Google Scholar
Raithby, P. R., Shields, G. P. & Allen, F. H. (1997). Acta Cryst. B53, 241–251. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shoham, G., Lipscomb, W. N. & Olsher, U. (1983). J. Chem. Soc. Chem. Commun. pp. 208–209. CrossRef Web of Science Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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