{2,2-Bis[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propane}bis­(N,N-di­methyl­formamide)copper(II) bis­(hexa­fluoridoantimonate)

Rehbein, J.; Schürmann, M.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536809020364

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m737

doi:10.1107/S1600536809020364

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{2,2-Bis[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propane}bis(N,N-dimethylformamide)copper(II) bis(hexafluoridoantimonate)

Julia Rehbein,^a Markus Schürmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

^aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
^*Correspondence e-mail: hans.preut@udo.edu

(Received 13 May 2009; accepted 28 May 2009; online 6 June 2009)

In the title compound, [Cu(C₁₇H₃₀N₂O₂)(C₃H₇NO)₂][SbF₆]₂, which is a potential catalyst in the asymmetric Gosteli–Claisen rearrangement, the Cu atom adopts a distorted cis-CuN₂O₂ square-planar geometry arising from N,N′-bidentate coordination by the chiral ligand and two O-bonded dimethylformamide molecules. Two short C—H⋯O contacts occur within the ligand and two weak intermolecular C—H⋯F bonds may help to establish the packing.

Related literature

For further synthetic details, see: Evans et al. (1981 , 1999 ); Meyers & McKennon (1993 ). For information on the catalytic properties of the title compound, see: Abraham et al. (2001 , 2004 ); Abraham & Hiersemann (2001 ); Hiersemann & Abraham (2002 ).

Experimental

Crystal data

[Cu(C₁₇H₃₀N₂O₂)(C₃H₇NO)₂][SbF₆]₂
M_r = 975.66
Monoclinic, P 2₁
a = 9.1550 (5) Å
b = 13.6852 (8) Å
c = 14.5359 (8) Å
β = 92.570 (5)°
V = 1819.34 (18) Å³
Z = 2
Mo Kα radiation
μ = 2.15 mm⁻¹
T = 173 K
0.18 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur-S CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.808, T_max = 1.000 (expected range = 0.741–0.918)
10322 measured reflections
6226 independent reflections
4042 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.048
S = 0.85
6226 reflections
407 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.67 e Å⁻³
Absolute structure: Flack (1983 ), 2689 Friedel pairs
Flack parameter: 0.015 (15)

Table 1
Selected geometric parameters (Å, °)

Cu—N1	1.929 (5)
Cu—N2	1.919 (5)
Cu—O11	1.926 (4)
Cu—O12	1.951 (4)

N2—Cu—O11	153.82 (19)
N2—Cu—N1	92.92 (17)
O11—Cu—N1	91.37 (19)
N2—Cu—O12	95.00 (19)
O11—Cu—O12	91.51 (17)
N1—Cu—O12	155.84 (18)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O11	0.98	2.58	3.204 (8)	122
C17—H17C⋯O12	0.98	2.58	3.189 (7)	120
C25—H25C⋯F13ⁱ	0.98	2.55	3.418 (8)	148
C26—H26B⋯F11ⁱ	0.98	2.53	3.427 (8)	152
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020364/hb2975sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020364/hb2975Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was tested as a catalyst in the catalytic asymmetric Gosteli-Claisen rearrangement (Abraham et al., 2001; Abraham & Hiersemann, 2001; Hiersemann & Abraham, 2002; Abraham et al., 2004). The synthesis of the title compound, (I), was accomplished according to a modified procedure of Evans et al. (1999). A sequence of Meyer's amino acid reduction of (S)-tert-Leucine (Meyers & McKennon, 1993), subsequent condensation with dimethyl malonic acid dichloride and p-TsCl catalyzed cyclization provided the (S,S)-t-Bu-box ligand. Treatment of the box ligand with CuCl₂ (Evans et al., 1981) and subsequent anion metathesis with AgSbF₆ provided [Cu(S,S)-t-Bu-box](SbF₆)₂. Addition of 2 eq of DMF to a solution of [Cu(S,S)-t-Bu-box](SbF₆)₂ in 1,2-dichloroethane afforded the bis(N,N-dimethylformamide) complex. Crystallization was achieved by vapor diffusion recrystalization at 243 K.

Related literature top

For further synthetic details, see: Evans et al. (1981, 1999); Meyers & McKennon (1993). For information on the catalytic properties of the title compound, see: Abraham et al. (2001, 2004); Abraham & Hiersemann (2001); Hiersemann & Abraham (2002).

Experimental top

To a solution of [Cu(S,S)-t-Bu-box](SbF₆)₂(15.4 mg, 17.3 mmol, 1 eq) in dry 1,2-dichloroethane (1 ml) under argon atmosphere, DMF (27 µL, 34.6 mmol, 2eq) was added by a microliter syringe and the resulting deep blue solution was stirred for 30 min at room temperature. Subsequent cooling to 243 K for 24 h provided (I) as deep blue crystals. IR (from a 0.05 M 1,2-dichloroethane solution, cm^-1): 1750 (w), 1680 (s); UV/vis (from a 0.05 M in 1,2-dichloroethane solution, nm): 255, 733.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level.

{2,2-Bis[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2- yl]propane}bis(N,N-dimethylformamide)copper(II) bis(hexafluoridoantimonate) top

Crystal data top

[Cu(C₁₇H₃₀N₂O₂)(C₃H₇NO)₂][SbF₆]₂	F(000) = 962
M_r = 975.66	D_x = 1.781 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3964 reflections
a = 9.1550 (5) Å	θ = 2.1–29.0°
b = 13.6852 (8) Å	µ = 2.15 mm⁻¹
c = 14.5359 (8) Å	T = 173 K
β = 92.570 (5)°	Plate, blue
V = 1819.34 (18) Å³	0.18 × 0.12 × 0.04 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur-S CCD diffractometer	6226 independent reflections
Radiation source: fine-focus sealed tube	4042 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 16.0560 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −16→16
T_min = 0.808, T_max = 1.000	l = −17→17
10322 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0061P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max = 0.001
6226 reflections	Δρ_max = 0.96 e Å⁻³
407 parameters	Δρ_min = −0.67 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2689 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (15)

Crystal data top

[Cu(C₁₇H₃₀N₂O₂)(C₃H₇NO)₂][SbF₆]₂	V = 1819.34 (18) Å³
M_r = 975.66	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.1550 (5) Å	µ = 2.15 mm⁻¹
b = 13.6852 (8) Å	T = 173 K
c = 14.5359 (8) Å	0.18 × 0.12 × 0.04 mm
β = 92.570 (5)°

Data collection top

Oxford Diffraction Xcalibur-S CCD diffractometer	6226 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	4042 reflections with I > 2σ(I)
T_min = 0.808, T_max = 1.000	R_int = 0.037
10322 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.048	Δρ_max = 0.96 e Å⁻³
S = 0.85	Δρ_min = −0.67 e Å⁻³
6226 reflections	Absolute structure: Flack (1983), 2689 Friedel pairs
407 parameters	Absolute structure parameter: 0.015 (15)
1 restraint

Special details top

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction 2008) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Sb1	0.24602 (5)	−0.00096 (4)	0.84532 (3)	0.02849 (13)
Sb2	0.82483 (6)	−0.04083 (3)	0.35372 (3)	0.04390 (17)
Cu	0.73163 (7)	0.00310 (7)	0.75133 (4)	0.01763 (19)
F1	0.2031 (5)	0.1198 (3)	0.7920 (4)	0.0916 (18)
F2	0.2546 (4)	−0.0541 (4)	0.7284 (3)	0.0698 (15)
F3	0.2369 (5)	0.0546 (4)	0.9607 (3)	0.101 (2)
F4	0.2858 (6)	−0.1211 (3)	0.8965 (3)	0.0863 (18)
F5	0.0475 (3)	−0.0245 (3)	0.8405 (2)	0.0477 (12)
F6	0.4443 (4)	0.0246 (3)	0.8467 (2)	0.0509 (14)
F11	0.7475 (5)	−0.1293 (3)	0.4335 (3)	0.0786 (18)
F12	0.9927 (4)	−0.0336 (4)	0.4310 (3)	0.0952 (17)
F13	0.9126 (5)	−0.1425 (4)	0.2906 (3)	0.0789 (17)
F14	0.7367 (5)	0.0599 (3)	0.4194 (3)	0.0686 (16)
F15	0.9021 (6)	0.0505 (4)	0.2763 (3)	0.099 (2)
F16	0.6569 (4)	−0.0534 (4)	0.2775 (3)	0.0743 (14)
O1	0.6721 (5)	−0.1668 (3)	0.9773 (3)	0.0260 (12)
O2	0.8559 (4)	0.1567 (3)	0.9822 (3)	0.0268 (12)
O11	0.6003 (4)	−0.0630 (3)	0.6648 (3)	0.0260 (12)
O12	0.8222 (5)	0.0741 (3)	0.6524 (3)	0.0201 (11)
N1	0.7133 (5)	−0.1001 (3)	0.8405 (3)	0.0103 (13)*
N2	0.7798 (5)	0.0988 (3)	0.8442 (3)	0.0119 (13)*
N11	0.4549 (6)	−0.0757 (5)	0.5361 (4)	0.0431 (19)
N12	1.0155 (6)	0.1349 (4)	0.5795 (4)	0.0252 (14)
C1	0.6719 (7)	−0.2052 (4)	0.8185 (4)	0.0171 (16)
H1A	0.5896	−0.2058	0.7709	0.020*
C2	0.6141 (7)	−0.2378 (5)	0.9112 (4)	0.0237 (19)
H2A	0.5059	−0.2375	0.9091	0.028*
H2B	0.6490	−0.3044	0.9274	0.028*
C3	0.7127 (7)	−0.0906 (5)	0.9287 (4)	0.0148 (16)*
C4	0.7635 (6)	−0.0028 (5)	0.9871 (3)	0.0161 (13)
C5	0.7986 (7)	0.0843 (5)	0.9312 (4)	0.0178 (16)*
C6	0.9016 (7)	0.2313 (4)	0.9176 (4)	0.0249 (18)
H6A	1.0080	0.2276	0.9086	0.030*
H6B	0.8772	0.2976	0.9394	0.030*
C7	0.8128 (7)	0.2058 (4)	0.8278 (4)	0.0157 (16)
H7A	0.8781	0.2113	0.7747	0.019*
C8	0.6355 (7)	0.0246 (4)	1.0491 (4)	0.030 (2)
H8A	0.5539	0.0509	1.0108	0.045*
H8B	0.6689	0.0740	1.0942	0.045*
H8C	0.6032	−0.0338	1.0815	0.045*
C9	0.8971 (6)	−0.0356 (5)	1.0481 (3)	0.0277 (17)
H9A	0.9769	−0.0540	1.0090	0.042*
H9B	0.8700	−0.0918	1.0855	0.042*
H9C	0.9289	0.0183	1.0886	0.042*
C11	0.7994 (8)	−0.2652 (5)	0.7835 (4)	0.0230 (18)
C12	0.8609 (7)	−0.2170 (5)	0.6982 (4)	0.0296 (19)
H12A	0.7815	−0.2061	0.6519	0.044*
H12B	0.9346	−0.2599	0.6726	0.044*
H12C	0.9059	−0.1543	0.7156	0.044*
C13	0.7361 (8)	−0.3652 (5)	0.7570 (5)	0.045 (2)
H13A	0.6503	−0.3566	0.7151	0.067*
H13B	0.7074	−0.3995	0.8126	0.067*
H13C	0.8101	−0.4036	0.7264	0.067*
C14	0.9207 (7)	−0.2766 (5)	0.8565 (4)	0.0298 (19)
H14A	0.9925	−0.3239	0.8357	0.045*
H14B	0.8798	−0.3000	0.9137	0.045*
H14C	0.9685	−0.2134	0.8676	0.045*
C15	0.6730 (7)	0.2668 (5)	0.8068 (4)	0.0193 (17)
C16	0.5724 (7)	0.2661 (5)	0.8884 (4)	0.0265 (19)
H16A	0.4857	0.3060	0.8734	0.040*
H16B	0.6250	0.2930	0.9429	0.040*
H16C	0.5424	0.1988	0.9009	0.040*
C17	0.5873 (6)	0.2255 (4)	0.7230 (4)	0.0217 (17)
H17A	0.5039	0.2681	0.7072	0.033*
H17B	0.5518	0.1599	0.7372	0.033*
H17C	0.6511	0.2219	0.6707	0.033*
C18	0.7186 (7)	0.3708 (4)	0.7858 (4)	0.026 (2)
H18A	0.6314	0.4105	0.7719	0.040*
H18B	0.7807	0.3708	0.7326	0.040*
H18C	0.7732	0.3981	0.8393	0.040*
C21	0.5522 (7)	−0.0297 (6)	0.5894 (4)	0.0280 (18)
H21A	0.5876	0.0317	0.5697	0.034*
C22	0.3949 (9)	−0.1684 (6)	0.5652 (6)	0.084 (3)
H22A	0.4454	−0.1893	0.6228	0.126*
H22B	0.4086	−0.2177	0.5175	0.126*
H22C	0.2903	−0.1607	0.5751	0.126*
C23	0.4080 (7)	−0.0386 (7)	0.4445 (4)	0.057 (3)
H23A	0.4425	0.0287	0.4377	0.086*
H23B	0.3010	−0.0400	0.4378	0.086*
H23C	0.4492	−0.0798	0.3970	0.086*
C24	0.9571 (8)	0.0712 (5)	0.6335 (4)	0.0281 (19)
H24A	1.0169	0.0208	0.6597	0.034*
C25	0.9337 (7)	0.2131 (5)	0.5394 (5)	0.042 (2)
H25A	0.8292	0.2014	0.5464	0.063*
H25B	0.9532	0.2177	0.4738	0.063*
H25C	0.9621	0.2744	0.5702	0.063*
C26	1.1697 (7)	0.1266 (5)	0.5580 (4)	0.042 (2)
H26A	1.2144	0.0720	0.5925	0.063*
H26B	1.2207	0.1874	0.5751	0.063*
H26C	1.1772	0.1151	0.4918	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0168 (3)	0.0299 (3)	0.0386 (3)	0.0007 (3)	−0.0009 (2)	0.0003 (3)
Sb2	0.0473 (4)	0.0535 (4)	0.0314 (3)	−0.0137 (3)	0.0082 (3)	−0.0042 (3)
Cu	0.0247 (5)	0.0150 (4)	0.0131 (4)	−0.0012 (5)	−0.0004 (3)	−0.0003 (5)
F1	0.081 (4)	0.043 (3)	0.149 (5)	0.000 (3)	−0.017 (4)	0.023 (3)
F2	0.051 (3)	0.109 (4)	0.050 (3)	0.010 (3)	0.003 (2)	−0.012 (3)
F3	0.060 (4)	0.174 (6)	0.071 (3)	−0.008 (4)	0.016 (3)	−0.074 (4)
F4	0.100 (5)	0.047 (3)	0.110 (5)	0.007 (3)	−0.021 (4)	0.038 (3)
F5	0.029 (2)	0.058 (4)	0.055 (2)	0.003 (2)	−0.0032 (17)	−0.001 (3)
F6	0.043 (3)	0.057 (4)	0.051 (3)	0.007 (2)	−0.003 (2)	−0.005 (2)
F11	0.092 (5)	0.070 (4)	0.078 (4)	0.020 (3)	0.047 (3)	0.034 (3)
F12	0.064 (3)	0.129 (5)	0.089 (4)	0.004 (4)	−0.034 (3)	−0.037 (4)
F13	0.063 (4)	0.092 (4)	0.084 (4)	−0.004 (3)	0.017 (3)	−0.036 (3)
F14	0.088 (4)	0.058 (3)	0.061 (3)	0.008 (3)	0.008 (3)	−0.011 (3)
F15	0.106 (5)	0.115 (5)	0.079 (4)	−0.056 (4)	0.039 (3)	0.012 (3)
F16	0.065 (3)	0.082 (4)	0.074 (3)	−0.013 (3)	−0.015 (3)	−0.008 (3)
O1	0.043 (3)	0.013 (3)	0.023 (3)	−0.011 (2)	0.008 (2)	0.004 (2)
O2	0.040 (3)	0.016 (3)	0.023 (3)	−0.009 (2)	−0.011 (2)	0.004 (2)
O11	0.038 (3)	0.024 (3)	0.015 (3)	−0.006 (2)	−0.019 (2)	0.004 (2)
O12	0.020 (3)	0.023 (3)	0.018 (3)	0.001 (2)	0.007 (2)	0.006 (2)
N11	0.038 (4)	0.065 (6)	0.026 (4)	0.007 (4)	−0.012 (3)	−0.021 (4)
N12	0.015 (3)	0.027 (4)	0.034 (4)	0.004 (3)	0.005 (3)	0.004 (3)
C1	0.019 (4)	0.015 (4)	0.017 (4)	−0.004 (3)	0.003 (3)	0.001 (3)
C2	0.025 (5)	0.019 (4)	0.027 (5)	−0.006 (4)	0.002 (4)	0.006 (4)
C4	0.020 (3)	0.014 (3)	0.014 (3)	0.000 (4)	−0.002 (3)	0.006 (4)
C6	0.041 (5)	0.006 (4)	0.027 (4)	−0.007 (3)	−0.012 (4)	0.005 (3)
C7	0.019 (4)	0.017 (4)	0.010 (4)	−0.004 (3)	−0.002 (3)	0.001 (3)
C8	0.045 (5)	0.027 (6)	0.020 (4)	−0.002 (4)	0.010 (3)	−0.012 (3)
C9	0.038 (4)	0.019 (4)	0.026 (4)	−0.002 (4)	−0.007 (3)	−0.005 (4)
C11	0.031 (5)	0.015 (4)	0.023 (5)	0.009 (4)	0.001 (4)	−0.003 (4)
C12	0.030 (5)	0.036 (5)	0.023 (4)	0.005 (4)	0.008 (4)	−0.004 (4)
C13	0.053 (6)	0.030 (5)	0.051 (6)	0.001 (5)	−0.002 (5)	−0.005 (5)
C14	0.028 (5)	0.032 (5)	0.028 (5)	−0.004 (4)	−0.014 (4)	0.003 (4)
C15	0.024 (5)	0.021 (4)	0.013 (4)	0.003 (4)	−0.002 (3)	−0.001 (3)
C16	0.031 (5)	0.031 (5)	0.017 (4)	0.012 (4)	−0.004 (4)	−0.005 (4)
C17	0.020 (4)	0.026 (4)	0.019 (4)	0.007 (3)	0.000 (3)	0.003 (3)
C18	0.044 (5)	0.015 (4)	0.020 (4)	−0.002 (4)	−0.006 (4)	−0.004 (4)
C21	0.020 (4)	0.029 (5)	0.035 (4)	−0.005 (4)	0.010 (3)	−0.010 (4)
C22	0.082 (8)	0.087 (8)	0.080 (8)	−0.037 (7)	−0.030 (6)	−0.005 (7)
C23	0.052 (5)	0.092 (7)	0.026 (4)	0.016 (6)	−0.017 (4)	−0.008 (6)
C24	0.031 (5)	0.026 (5)	0.028 (4)	−0.006 (4)	0.006 (4)	0.005 (4)
C25	0.030 (5)	0.040 (5)	0.056 (6)	−0.001 (4)	0.006 (4)	0.018 (4)
C26	0.022 (5)	0.053 (5)	0.052 (5)	−0.004 (4)	0.005 (4)	0.005 (5)

Geometric parameters (Å, º) top

Sb1—F4	1.834 (4)	C7—H7A	1.0000
Sb1—F5	1.844 (3)	C8—H8A	0.9800
Sb1—F3	1.847 (4)	C8—H8B	0.9800
Sb1—F6	1.848 (4)	C8—H8C	0.9800
Sb1—F2	1.853 (4)	C9—H9A	0.9800
Sb1—F1	1.859 (4)	C9—H9B	0.9800
Sb2—F11	1.840 (4)	C9—H9C	0.9800
Sb2—F15	1.844 (4)	C11—C14	1.509 (8)
Sb2—F16	1.862 (4)	C11—C13	1.528 (9)
Sb2—F12	1.865 (4)	C11—C12	1.534 (8)
Sb2—F13	1.868 (5)	C12—H12A	0.9800
Sb2—F14	1.879 (4)	C12—H12B	0.9800
Cu—N1	1.929 (5)	C12—H12C	0.9800
Cu—N2	1.919 (5)	C13—H13A	0.9800
Cu—O11	1.926 (4)	C13—H13B	0.9800
Cu—O12	1.951 (4)	C13—H13C	0.9800
O1—C3	1.322 (6)	C14—H14A	0.9800
O1—C2	1.450 (7)	C14—H14B	0.9800
O2—C5	1.331 (7)	C14—H14C	0.9800
O2—C6	1.461 (6)	C15—C18	1.518 (8)
O11—C21	1.249 (7)	C15—C17	1.528 (8)
O12—C24	1.277 (7)	C15—C16	1.534 (8)
N1—C3	1.288 (7)	C16—H16A	0.9800
N1—C1	1.518 (7)	C16—H16B	0.9800
N2—C5	1.283 (7)	C16—H16C	0.9800
N2—C7	1.516 (7)	C17—H17A	0.9800
N11—C21	1.314 (7)	C17—H17B	0.9800
N11—C22	1.453 (9)	C17—H17C	0.9800
N11—C23	1.471 (7)	C18—H18A	0.9800
N12—C24	1.303 (7)	C18—H18B	0.9800
N12—C25	1.418 (7)	C18—H18C	0.9800
N12—C26	1.464 (7)	C21—H21A	0.9500
C1—C11	1.532 (8)	C22—H22A	0.9800
C1—C2	1.536 (8)	C22—H22B	0.9800
C1—H1A	1.0000	C22—H22C	0.9800
C2—H2A	0.9900	C23—H23A	0.9800
C2—H2B	0.9900	C23—H23B	0.9800
C3—C4	1.532 (8)	C23—H23C	0.9800
C4—C5	1.486 (8)	C24—H24A	0.9500
C4—C9	1.545 (7)	C25—H25A	0.9800
C4—C8	1.556 (7)	C25—H25B	0.9800
C6—C7	1.546 (8)	C25—H25C	0.9800
C6—H6A	0.9900	C26—H26A	0.9800
C6—H6B	0.9900	C26—H26B	0.9800
C7—C15	1.547 (8)	C26—H26C	0.9800

F4—Sb1—F5	92.1 (2)	C4—C8—H8B	109.5
F4—Sb1—F3	91.0 (3)	H8A—C8—H8B	109.5
F5—Sb1—F3	91.25 (17)	C4—C8—H8C	109.5
F4—Sb1—F6	89.3 (2)	H8A—C8—H8C	109.5
F5—Sb1—F6	178.25 (17)	H8B—C8—H8C	109.5
F3—Sb1—F6	89.81 (18)	C4—C9—H9A	109.5
F4—Sb1—F2	90.3 (2)	C4—C9—H9B	109.5
F5—Sb1—F2	88.80 (16)	H9A—C9—H9B	109.5
F3—Sb1—F2	178.8 (3)	C4—C9—H9C	109.5
F6—Sb1—F2	90.10 (17)	H9A—C9—H9C	109.5
F4—Sb1—F1	179.0 (2)	H9B—C9—H9C	109.5
F5—Sb1—F1	87.15 (19)	C14—C11—C13	110.1 (6)
F3—Sb1—F1	89.7 (3)	C14—C11—C1	111.7 (5)
F6—Sb1—F1	91.5 (2)	C13—C11—C1	106.1 (6)
F2—Sb1—F1	89.1 (2)	C14—C11—C12	109.1 (6)
F11—Sb2—F15	178.4 (2)	C13—C11—C12	109.3 (5)
F11—Sb2—F16	89.0 (2)	C1—C11—C12	110.5 (5)
F15—Sb2—F16	91.6 (2)	C11—C12—H12A	109.5
F11—Sb2—F12	89.2 (2)	C11—C12—H12B	109.5
F15—Sb2—F12	90.2 (2)	H12A—C12—H12B	109.5
F16—Sb2—F12	177.7 (2)	C11—C12—H12C	109.5
F11—Sb2—F13	90.3 (2)	H12A—C12—H12C	109.5
F15—Sb2—F13	91.1 (2)	H12B—C12—H12C	109.5
F16—Sb2—F13	90.0 (2)	C11—C13—H13A	109.5
F12—Sb2—F13	88.5 (2)	C11—C13—H13B	109.5
F11—Sb2—F14	88.66 (18)	H13A—C13—H13B	109.5
F15—Sb2—F14	89.9 (2)	C11—C13—H13C	109.5
F16—Sb2—F14	90.5 (2)	H13A—C13—H13C	109.5
F12—Sb2—F14	90.9 (2)	H13B—C13—H13C	109.5
F13—Sb2—F14	178.9 (2)	C11—C14—H14A	109.5
N2—Cu—O11	153.82 (19)	C11—C14—H14B	109.5
N2—Cu—N1	92.92 (17)	H14A—C14—H14B	109.5
O11—Cu—N1	91.37 (19)	C11—C14—H14C	109.5
N2—Cu—O12	95.00 (19)	H14A—C14—H14C	109.5
O11—Cu—O12	91.51 (17)	H14B—C14—H14C	109.5
N1—Cu—O12	155.84 (18)	C18—C15—C17	108.8 (5)
C3—O1—C2	106.1 (5)	C18—C15—C16	109.9 (5)
C5—O2—C6	106.2 (5)	C17—C15—C16	108.0 (6)
C21—O11—Cu	125.9 (5)	C18—C15—C7	108.3 (5)
C24—O12—Cu	126.2 (4)	C17—C15—C7	110.4 (5)
C3—N1—C1	107.0 (5)	C16—C15—C7	111.3 (5)
C3—N1—Cu	126.8 (4)	C15—C16—H16A	109.5
C1—N1—Cu	125.5 (4)	C15—C16—H16B	109.5
C5—N2—C7	106.6 (5)	H16A—C16—H16B	109.5
C5—N2—Cu	127.2 (4)	C15—C16—H16C	109.5
C7—N2—Cu	126.1 (4)	H16A—C16—H16C	109.5
C21—N11—C22	120.1 (6)	H16B—C16—H16C	109.5
C21—N11—C23	122.1 (7)	C15—C17—H17A	109.5
C22—N11—C23	117.8 (6)	C15—C17—H17B	109.5
C24—N12—C25	122.0 (6)	H17A—C17—H17B	109.5
C24—N12—C26	120.2 (6)	C15—C17—H17C	109.5
C25—N12—C26	117.8 (5)	H17A—C17—H17C	109.5
N1—C1—C11	113.0 (5)	H17B—C17—H17C	109.5
N1—C1—C2	100.5 (5)	C15—C18—H18A	109.5
C11—C1—C2	115.7 (5)	C15—C18—H18B	109.5
N1—C1—H1A	109.1	H18A—C18—H18B	109.5
C11—C1—H1A	109.1	C15—C18—H18C	109.5
C2—C1—H1A	109.1	H18A—C18—H18C	109.5
O1—C2—C1	104.9 (5)	H18B—C18—H18C	109.5
O1—C2—H2A	110.8	O11—C21—N11	123.1 (7)
C1—C2—H2A	110.8	O11—C21—H21A	118.5
O1—C2—H2B	110.8	N11—C21—H21A	118.5
C1—C2—H2B	110.8	N11—C22—H22A	109.5
H2A—C2—H2B	108.8	N11—C22—H22B	109.5
N1—C3—O1	117.8 (6)	H22A—C22—H22B	109.5
N1—C3—C4	128.0 (6)	N11—C22—H22C	109.5
O1—C3—C4	114.1 (5)	H22A—C22—H22C	109.5
C5—C4—C3	113.2 (4)	H22B—C22—H22C	109.5
C5—C4—C9	111.2 (5)	N11—C23—H23A	109.5
C3—C4—C9	107.6 (5)	N11—C23—H23B	109.5
C5—C4—C8	108.1 (5)	H23A—C23—H23B	109.5
C3—C4—C8	107.0 (5)	N11—C23—H23C	109.5
C9—C4—C8	109.5 (4)	H23A—C23—H23C	109.5
N2—C5—O2	117.8 (6)	H23B—C23—H23C	109.5
N2—C5—C4	129.8 (6)	O12—C24—N12	122.4 (7)
O2—C5—C4	112.4 (5)	O12—C24—H24A	118.8
O2—C6—C7	103.3 (5)	N12—C24—H24A	118.8
O2—C6—H6A	111.1	N12—C25—H25A	109.5
C7—C6—H6A	111.1	N12—C25—H25B	109.5
O2—C6—H6B	111.1	H25A—C25—H25B	109.5
C7—C6—H6B	111.1	N12—C25—H25C	109.5
H6A—C6—H6B	109.1	H25A—C25—H25C	109.5
N2—C7—C6	100.7 (4)	H25B—C25—H25C	109.5
N2—C7—C15	112.5 (5)	N12—C26—H26A	109.5
C6—C7—C15	116.3 (5)	N12—C26—H26B	109.5
N2—C7—H7A	108.9	H26A—C26—H26B	109.5
C6—C7—H7A	108.9	N12—C26—H26C	109.5
C15—C7—H7A	108.9	H26A—C26—H26C	109.5
C4—C8—H8A	109.5	H26B—C26—H26C	109.5

N2—Cu—O11—C21	74.3 (6)	C7—N2—C5—O2	−7.8 (8)
N1—Cu—O11—C21	173.7 (5)	Cu—N2—C5—O2	168.6 (4)
O12—Cu—O11—C21	−30.3 (5)	C7—N2—C5—C4	171.1 (6)
N2—Cu—O12—C24	84.8 (5)	Cu—N2—C5—C4	−12.5 (10)
O11—Cu—O12—C24	−120.6 (5)	C6—O2—C5—N2	−8.0 (8)
N1—Cu—O12—C24	−23.9 (8)	C6—O2—C5—C4	172.9 (5)
N2—Cu—N1—C3	9.6 (6)	C3—C4—C5—N2	7.2 (10)
O11—Cu—N1—C3	−144.6 (5)	C9—C4—C5—N2	128.5 (7)
O12—Cu—N1—C3	118.7 (6)	C8—C4—C5—N2	−111.2 (7)
N2—Cu—N1—C1	178.9 (4)	C3—C4—C5—O2	−173.9 (5)
O11—Cu—N1—C1	24.8 (5)	C9—C4—C5—O2	−52.5 (7)
O12—Cu—N1—C1	−72.0 (7)	C8—C4—C5—O2	67.8 (6)
O11—Cu—N2—C5	103.2 (6)	C5—O2—C6—C7	19.3 (6)
N1—Cu—N2—C5	4.1 (6)	C5—N2—C7—C6	18.7 (6)
O12—Cu—N2—C5	−153.1 (5)	Cu—N2—C7—C6	−157.7 (4)
O11—Cu—N2—C7	−81.1 (6)	C5—N2—C7—C15	−105.8 (6)
N1—Cu—N2—C7	179.8 (4)	Cu—N2—C7—C15	77.7 (6)
O12—Cu—N2—C7	22.6 (5)	O2—C6—C7—N2	−22.4 (6)
C3—N1—C1—C11	−110.4 (6)	O2—C6—C7—C15	99.5 (6)
Cu—N1—C1—C11	78.6 (6)	N1—C1—C11—C14	64.9 (7)
C3—N1—C1—C2	13.5 (6)	C2—C1—C11—C14	−50.2 (8)
Cu—N1—C1—C2	−157.5 (4)	N1—C1—C11—C13	−175.2 (5)
C3—O1—C2—C1	17.6 (6)	C2—C1—C11—C13	69.7 (7)
N1—C1—C2—O1	−18.4 (6)	N1—C1—C11—C12	−56.9 (7)
C11—C1—C2—O1	103.7 (6)	C2—C1—C11—C12	−172.0 (5)
C1—N1—C3—O1	−3.2 (7)	N2—C7—C15—C18	−176.6 (5)
Cu—N1—C3—O1	167.7 (4)	C6—C7—C15—C18	67.9 (7)
C1—N1—C3—C4	172.4 (6)	N2—C7—C15—C17	−57.5 (6)
Cu—N1—C3—C4	−16.7 (9)	C6—C7—C15—C17	−173.0 (5)
C2—O1—C3—N1	−9.6 (7)	N2—C7—C15—C16	62.4 (7)
C2—O1—C3—C4	174.2 (5)	C6—C7—C15—C16	−53.1 (8)
N1—C3—C4—C5	8.3 (9)	Cu—O11—C21—N11	−175.2 (4)
O1—C3—C4—C5	−175.9 (5)	C22—N11—C21—O11	1.8 (10)
N1—C3—C4—C9	−115.0 (7)	C23—N11—C21—O11	−175.3 (5)
O1—C3—C4—C9	60.7 (6)	Cu—O12—C24—N12	−165.4 (4)
N1—C3—C4—C8	127.3 (6)	C25—N12—C24—O12	1.2 (10)
O1—C3—C4—C8	−56.9 (7)	C26—N12—C24—O12	−178.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O11	0.98	2.58	3.204 (8)	122
C17—H17C···O12	0.98	2.58	3.189 (7)	120
C25—H25C···F13ⁱ	0.98	2.55	3.418 (8)	148
C26—H26B···F11ⁱ	0.98	2.53	3.427 (8)	152

Symmetry code: (i) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₃₀N₂O₂)(C₃H₇NO)₂][SbF₆]₂
M_r	975.66
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	9.1550 (5), 13.6852 (8), 14.5359 (8)
β (°)	92.570 (5)
V (Å³)	1819.34 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.18 × 0.12 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur-S CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.808, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10322, 6226, 4042
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.048, 0.85
No. of reflections	6226
No. of parameters	407
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.67
Absolute structure	Flack (1983), 2689 Friedel pairs
Absolute structure parameter	0.015 (15)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Cu—N1	1.929 (5)	Cu—O11	1.926 (4)
Cu—N2	1.919 (5)	Cu—O12	1.951 (4)

N2—Cu—O11	153.82 (19)	N2—Cu—O12	95.00 (19)
N2—Cu—N1	92.92 (17)	O11—Cu—O12	91.51 (17)
O11—Cu—N1	91.37 (19)	N1—Cu—O12	155.84 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O11	0.98	2.58	3.204 (8)	122
C17—H17C···O12	0.98	2.58	3.189 (7)	120
C25—H25C···F13ⁱ	0.98	2.55	3.418 (8)	148
C26—H26B···F11ⁱ	0.98	2.53	3.427 (8)	152

Symmetry code: (i) −x+2, y+1/2, −z+1.

References

Abraham, L., Czerwonka, R. & Hiersemann, M. (2001). Angew. Chem. Int. Ed. 40, 4700–4703. Web of Science CrossRef CAS Google Scholar
Abraham, L. & Hiersemann, M. (2001). Org. Lett. 3, 48–52. Google Scholar
Abraham, L., Körner, M. & Hiersemann, M. (2004). Adv. Synth. Catal. 346, 1281–1294. Web of Science CSD CrossRef CAS Google Scholar
Evans, D. A., Bartroli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127–2129. CrossRef CAS Web of Science Google Scholar
Evans, D. A., Miller, S. J., Lectka, T. & von Matt, P. (1999). J. Am. Chem. Soc. 121, 7559–7573. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hiersemann, M. & Abraham, L. (2002). Eur. J. Org. Chem. pp. 1461–1471. CrossRef Google Scholar
Meyers, A. I. & McKennon, M. J. (1993). J. Org. Chem. 58, 3568–3571. Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Page m737

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{2,2-Bis[(4S)-4-tert-butyl-4,5-di­hydro-1,3-oxazol-2-yl]propane}bis­­(N,N-di­methyl­formamide)copper(II) bis­­(hexa­fluorido­antimonate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

{2,2-Bis[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]propane}bis(N,N-dimethylformamide)copper(II) bis(hexafluoridoantimonate)