{2,2-Bis[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]propane}-bis-(N,N-dimethyl-formamide)-copper(II) bis-[hexa-fluoridoanti-monate(V)].

In the title compound, [Cu(C(15)H(26)N(2)O(2))(C(3)H(7)NO)(2)][SbF(6)](2), which is a potential catalyst in the catalytic asymmetric Gosteli-Claisen rearrangement, the central Cu(II) atom is in a nearly square-planar cis-N(2)O(2) environment in the cation arising from its coordination by an N,N-bidentate 2,2-bis-[(4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl]propane ligand and two O-bonded N,N-dimethyl-formamide mol-ecules. Two SbF(6) (-) anions are positioned on opposite sides of the plane through the CuN(2)O(2) unit, generating an axially distorted CuN(2)O(2)F(2) octa-hedral geometry for the metal ion.

Related literature

For background to the catalytic asymmetric Gosteli–Claisen rearrangement, see: Abraham & Hiersemann (2001 ▶); Abraham et al. (2001 ▶, 2004 ▶); Hiersemann & Abraham (2002 ▶). For further synthetic details, see: Evans et al. (1991 ▶, 1998 ▶); McKennon et al. (1993 ▶). For application of the catalytic asymmetric Gosteli–Claisen rearrangement, see: Körner & Hiersemann (2007 ▶); Pollex & Hiersemann (2005 ▶).

Experimental

Crystal data

[Cu(C15H26N2O2)(C3H7NO)2][SbF6]2

M = 947.61

Orthorhombic,

a = 9.7256 (2) Å

b = 15.2444 (3) Å

c = 23.2040 (5) Å

V = 3440.25 (12) Å3

Z = 4

Mo Kα radiation

μ = 2.27 mm−1

T = 173 K

0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.820, T max = 1.000

41873 measured reflections

7479 independent reflections

6078 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.037

S = 1.04

7479 reflections

407 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.52 e Å−3

Absolute structure: Flack (1983 ▶), 2727 Friedel pairs

Flack parameter: −0.008 (10)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis CCD; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048658/hb5747sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048658/hb5747Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C15H26N2O2)(C3H7NO)2][SbF6]2	F(000) = 1860
Mr = 947.61	Dx = 1.830 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18634 reflections
a = 9.7256 (2) Å	θ = 2.2–29.1°
b = 15.2444 (3) Å	µ = 2.27 mm−1
c = 23.2040 (5) Å	T = 173 K
V = 3440.25 (12) Å3	Block, blue
Z = 4	0.30 × 0.20 × 0.10 mm

Oxford Diffraction Xcalibur S CCD diffractometer	7479 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6078 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 16.0560 pixels mm-1	θmax = 27.0°, θmin = 2.2°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −20→20
Tmin = 0.820, Tmax = 1.000	l = −29→29
41873 measured reflections

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)] = 0.027	H-atom parameters constrained
wR(F2) = 0.037	w = 1/[σ2(Fo2) + (0.0104P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
7479 reflections	Δρmax = 0.81 e Å−3
407 parameters	Δρmin = −0.52 e Å−3
0 restraints	Absolute structure: Flack (1983), 3264 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.008 (10)

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.37 (release 24-10-2008) Empirical absorption correction using sperical 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.

	x	y	z	Uiso*/Ueq
C1	0.5137 (4)	−0.0127 (2)	0.49613 (13)	0.0289 (9)
H1	0.4400	−0.0272	0.5213	0.035*
C2	0.6042 (3)	−0.0081 (2)	0.40077 (13)	0.0401 (10)
H2A	0.6808	0.0202	0.4210	0.060*
H2B	0.5682	0.0317	0.3712	0.060*
H2C	0.6367	−0.0622	0.3825	0.060*
C3	0.3714 (4)	−0.0676 (3)	0.41833 (15)	0.0533 (12)
H3A	0.3091	−0.0825	0.4500	0.080*
H3B	0.3947	−0.1209	0.3968	0.080*
H3C	0.3264	−0.0256	0.3925	0.080*
C4	0.4588 (3)	0.1619 (2)	0.58081 (13)	0.0256 (8)
H4	0.5160	0.1732	0.5484	0.031*
C5	0.2758 (4)	0.2059 (3)	0.64305 (15)	0.0542 (12)
H5A	0.2778	0.1441	0.6548	0.081*
H5B	0.1810	0.2231	0.6343	0.081*
H5C	0.3114	0.2425	0.6744	0.081*
C6	0.3425 (4)	0.2977 (2)	0.55892 (15)	0.0454 (10)
H6A	0.3591	0.3486	0.5837	0.068*
H6B	0.2484	0.3001	0.5439	0.068*
H6C	0.4078	0.2982	0.5268	0.068*
C7	0.4543 (3)	0.0165 (2)	0.74066 (13)	0.0287 (9)
H7	0.4068	0.0057	0.7031	0.034*
C8	0.4871 (4)	−0.0730 (2)	0.76668 (15)	0.0483 (12)
H8A	0.5467	−0.1059	0.7403	0.073*
H8B	0.4015	−0.1057	0.7728	0.073*
H8C	0.5342	−0.0651	0.8036	0.073*
C9	0.3533 (4)	0.0675 (3)	0.77929 (14)	0.0444 (11)
H9A	0.3973	0.0803	0.8164	0.067*
H9B	0.2707	0.0320	0.7857	0.067*
H9C	0.3278	0.1226	0.7604	0.067*
C10	0.5804 (3)	0.0722 (2)	0.72801 (12)	0.0211 (8)
H10	0.5518	0.1305	0.7123	0.025*
C11	0.6784 (4)	0.0848 (2)	0.77903 (13)	0.0324 (9)
H11A	0.7194	0.1443	0.7786	0.039*
H11B	0.6298	0.0761	0.8161	0.039*
C12	0.7743 (3)	−0.0033 (2)	0.71476 (13)	0.0253 (8)
C13	0.8862 (3)	−0.0654 (2)	0.69651 (13)	0.0299 (9)
C14	0.8660 (4)	−0.1533 (2)	0.72814 (14)	0.0482 (11)
H14A	0.8620	−0.1428	0.7698	0.072*
H14B	0.9432	−0.1924	0.7194	0.072*
H14C	0.7800	−0.1806	0.7153	0.072*
C15	1.0259 (3)	−0.0252 (3)	0.71247 (15)	0.0457 (11)
H15A	1.0368	0.0312	0.6927	0.069*
H15B	1.0997	−0.0650	0.7006	0.069*
H15C	1.0303	−0.0161	0.7542	0.069*
C16	0.8874 (3)	−0.0824 (2)	0.63266 (13)	0.0241 (8)
C17	0.9624 (4)	−0.1531 (2)	0.55485 (14)	0.0317 (9)
H17A	0.9144	−0.2091	0.5469	0.038*
H17B	1.0517	−0.1530	0.5343	0.038*
C18	0.8747 (3)	−0.0751 (2)	0.53675 (13)	0.0221 (8)
H18	0.7999	−0.0951	0.5103	0.027*
C19	0.9522 (4)	0.0016 (2)	0.50941 (13)	0.0295 (9)
H19	0.8849	0.0508	0.5049	0.035*
C20	1.0693 (4)	0.0358 (2)	0.54629 (15)	0.0429 (10)
H20A	1.0330	0.0564	0.5833	0.064*
H20B	1.1149	0.0845	0.5264	0.064*
H20C	1.1358	−0.0114	0.5530	0.064*
C21	1.0018 (4)	−0.0230 (3)	0.44894 (15)	0.0426 (10)
H21A	1.0490	0.0273	0.4316	0.064*
H21B	0.9227	−0.0393	0.4251	0.064*
H21C	1.0654	−0.0726	0.4515	0.064*
Cu	0.64767 (4)	0.02331 (2)	0.602048 (15)	0.01965 (9)
F1	0.8666 (3)	0.37550 (14)	0.65651 (10)	0.0660 (8)
F2	0.7212 (2)	0.32927 (15)	0.56382 (10)	0.0693 (8)
F3	0.6661 (2)	0.25671 (14)	0.66418 (9)	0.0605 (7)
F4	0.9252 (2)	0.20713 (17)	0.67247 (9)	0.0705 (7)
F5	0.77901 (19)	0.16435 (12)	0.58166 (8)	0.0398 (5)
F6	0.97787 (19)	0.28174 (17)	0.57245 (9)	0.0569 (6)
F7	0.5062 (2)	−0.10547 (12)	0.61729 (9)	0.0539 (6)
F8	0.3044 (3)	−0.15540 (19)	0.54937 (11)	0.0903 (10)
F9	0.5315 (3)	−0.2408 (2)	0.55262 (12)	0.1229 (13)
F10	0.3038 (3)	−0.31014 (16)	0.59552 (11)	0.1034 (10)
F11	0.5076 (3)	−0.26059 (18)	0.66505 (11)	0.0897 (9)
F12	0.2818 (2)	−0.1733 (2)	0.66203 (12)	0.0942 (10)
N1	0.4964 (3)	−0.02873 (19)	0.44157 (11)	0.0281 (7)
N2	0.3604 (3)	0.21768 (18)	0.59222 (10)	0.0273 (7)
N3	0.6737 (3)	0.02687 (16)	0.68626 (9)	0.0188 (6)
N4	0.8145 (3)	−0.04765 (16)	0.59293 (10)	0.0192 (6)
O1	0.6184 (2)	0.01985 (15)	0.51831 (8)	0.0240 (5)
O2	0.4822 (2)	0.09465 (13)	0.60992 (9)	0.0232 (5)
O3	0.7822 (2)	0.01878 (17)	0.77070 (9)	0.0345 (6)
O4	0.9819 (2)	−0.14044 (14)	0.61644 (10)	0.0347 (6)
Sb1	0.82253 (2)	0.270184 (15)	0.619240 (9)	0.02832 (6)
Sb2	0.40579 (2)	−0.208325 (15)	0.607463 (10)	0.03231 (6)

	U11	U22	U33	U12	U13	U23
C1	0.037 (2)	0.032 (2)	0.0181 (19)	0.007 (2)	0.0039 (16)	0.0065 (17)
C2	0.046 (2)	0.056 (3)	0.0185 (18)	0.013 (2)	0.0007 (17)	−0.0003 (17)
C3	0.058 (3)	0.071 (3)	0.030 (2)	−0.024 (3)	−0.0164 (19)	0.002 (2)
C4	0.026 (2)	0.032 (2)	0.0195 (18)	−0.0009 (19)	0.0029 (15)	−0.0005 (17)
C5	0.046 (2)	0.073 (3)	0.043 (2)	0.040 (3)	0.0168 (18)	0.009 (2)
C6	0.051 (3)	0.034 (2)	0.051 (2)	0.017 (2)	−0.004 (2)	0.0040 (19)
C7	0.033 (2)	0.041 (2)	0.0115 (17)	−0.015 (2)	0.0025 (14)	0.0001 (16)
C8	0.065 (3)	0.048 (3)	0.032 (2)	−0.015 (2)	0.011 (2)	0.007 (2)
C9	0.046 (3)	0.061 (3)	0.026 (2)	−0.014 (2)	0.0115 (18)	−0.0117 (19)
C10	0.0221 (19)	0.028 (2)	0.0135 (16)	0.0001 (18)	−0.0008 (14)	−0.0016 (14)
C11	0.034 (2)	0.041 (2)	0.0223 (18)	0.004 (2)	0.0015 (17)	−0.0109 (16)
C12	0.025 (2)	0.032 (2)	0.0185 (18)	−0.0036 (18)	−0.0003 (14)	0.0049 (16)
C13	0.032 (2)	0.035 (2)	0.0219 (18)	0.005 (2)	−0.0057 (15)	0.0043 (16)
C14	0.066 (3)	0.047 (3)	0.032 (2)	0.014 (2)	0.000 (2)	0.0125 (19)
C15	0.039 (2)	0.072 (3)	0.027 (2)	0.015 (2)	−0.0120 (17)	−0.013 (2)
C16	0.025 (2)	0.0183 (18)	0.0286 (19)	−0.0002 (17)	0.0016 (15)	0.0023 (15)
C17	0.038 (2)	0.023 (2)	0.034 (2)	0.0064 (19)	0.0071 (17)	−0.0083 (17)
C18	0.020 (2)	0.023 (2)	0.0231 (18)	0.0025 (17)	0.0029 (13)	−0.0055 (15)
C19	0.034 (2)	0.030 (2)	0.0244 (19)	0.0044 (19)	0.0065 (15)	−0.0016 (16)
C20	0.046 (3)	0.038 (2)	0.044 (2)	−0.010 (2)	0.008 (2)	0.000 (2)
C21	0.042 (2)	0.050 (3)	0.036 (2)	0.000 (2)	0.0171 (18)	−0.004 (2)
Cu	0.0244 (2)	0.0223 (2)	0.01230 (19)	0.00190 (19)	0.00036 (16)	0.00085 (17)
F1	0.089 (2)	0.0442 (14)	0.0649 (17)	−0.0308 (14)	0.0121 (13)	−0.0198 (12)
F2	0.0860 (19)	0.0492 (16)	0.0727 (18)	0.0242 (14)	−0.0256 (14)	0.0122 (13)
F3	0.0603 (13)	0.0506 (15)	0.0704 (15)	−0.0135 (13)	0.0353 (12)	−0.0259 (12)
F4	0.0802 (17)	0.0779 (18)	0.0534 (14)	0.0076 (17)	−0.0219 (12)	0.0184 (15)
F5	0.0443 (13)	0.0282 (12)	0.0470 (13)	−0.0084 (10)	0.0141 (9)	−0.0097 (10)
F6	0.0401 (12)	0.0687 (18)	0.0618 (14)	−0.0192 (14)	0.0148 (10)	−0.0022 (14)
F7	0.0751 (15)	0.0443 (13)	0.0422 (14)	−0.0327 (11)	−0.0080 (12)	0.0008 (12)
F8	0.0765 (19)	0.108 (2)	0.0861 (19)	−0.0432 (18)	−0.0446 (16)	0.0576 (17)
F9	0.123 (2)	0.145 (3)	0.101 (2)	−0.017 (2)	0.0507 (19)	−0.077 (2)
F10	0.166 (3)	0.0594 (18)	0.085 (2)	−0.0660 (19)	−0.0287 (19)	0.0046 (15)
F11	0.097 (2)	0.068 (2)	0.105 (2)	0.0046 (16)	−0.0373 (16)	0.0335 (18)
F12	0.0541 (17)	0.135 (3)	0.094 (2)	−0.0123 (17)	0.0283 (14)	−0.028 (2)
N1	0.0313 (17)	0.0369 (19)	0.0161 (15)	0.0008 (16)	−0.0018 (13)	0.0025 (14)
N2	0.0270 (15)	0.0310 (17)	0.0238 (14)	0.0080 (16)	−0.0014 (11)	0.0036 (13)
N3	0.0200 (15)	0.0206 (15)	0.0159 (13)	−0.0055 (15)	0.0026 (12)	0.0018 (11)
N4	0.0227 (15)	0.0151 (14)	0.0197 (14)	0.0004 (14)	0.0028 (12)	0.0004 (11)
O1	0.0245 (14)	0.0312 (14)	0.0164 (12)	0.0012 (12)	−0.0031 (9)	−0.0015 (10)
O2	0.0267 (12)	0.0247 (12)	0.0184 (12)	0.0055 (10)	0.0031 (10)	0.0070 (11)
O3	0.0385 (15)	0.0518 (18)	0.0131 (12)	0.0099 (14)	−0.0065 (10)	−0.0055 (12)
O4	0.0393 (14)	0.0307 (14)	0.0340 (15)	0.0170 (12)	−0.0026 (12)	−0.0011 (13)
Sb1	0.03023 (13)	0.02309 (12)	0.03164 (13)	−0.00408 (12)	−0.00031 (11)	−0.00031 (11)
Sb2	0.04411 (15)	0.02205 (13)	0.03076 (13)	−0.00479 (12)	−0.00402 (11)	−0.00098 (11)

C1—O1	1.245 (4)	C13—C14	1.540 (5)
C1—N1	1.300 (4)	C14—H14A	0.9800
C1—H1	0.9500	C14—H14B	0.9800
C2—N1	1.448 (4)	C14—H14C	0.9800
C2—H2A	0.9800	C15—H15A	0.9800
C2—H2B	0.9800	C15—H15B	0.9800
C2—H2C	0.9800	C15—H15C	0.9800
C3—N1	1.456 (4)	C16—N4	1.278 (4)
C3—H3A	0.9800	C16—O4	1.330 (4)
C3—H3B	0.9800	C17—O4	1.455 (4)
C3—H3C	0.9800	C17—C18	1.523 (4)
C4—O2	1.249 (4)	C17—H17A	0.9900
C4—N2	1.307 (4)	C17—H17B	0.9900
C4—H4	0.9500	C18—N4	1.489 (4)
C5—N2	1.450 (4)	C18—C19	1.529 (4)
C5—H5A	0.9800	C18—H18	1.0000
C5—H5B	0.9800	C19—C20	1.517 (4)
C5—H5C	0.9800	C19—C21	1.530 (4)
C6—N2	1.454 (4)	C19—H19	1.0000
C6—H6A	0.9800	C20—H20A	0.9800
C6—H6B	0.9800	C20—H20B	0.9800
C6—H6C	0.9800	C20—H20C	0.9800
C7—C10	1.521 (4)	C21—H21A	0.9800
C7—C8	1.526 (5)	C21—H21B	0.9800
C7—C9	1.540 (5)	C21—H21C	0.9800
C7—H7	1.0000	Cu—O2	1.951 (2)
C8—H8A	0.9800	Cu—N4	1.962 (2)
C8—H8B	0.9800	Cu—O1	1.964 (2)
C8—H8C	0.9800	Cu—N3	1.971 (2)
C9—H9A	0.9800	Cu—F7	2.4232 (18)
C9—H9B	0.9800	Cu—F5	2.5452 (19)
C9—H9C	0.9800	F1—Sb1	1.873 (2)
C10—N3	1.497 (4)	F2—Sb1	1.854 (2)
C10—C11	1.532 (4)	F3—Sb1	1.8560 (18)
C10—H10	1.0000	F4—Sb1	1.856 (2)
C11—O3	1.439 (4)	F5—Sb1	1.8822 (18)
C11—H11A	0.9900	F6—Sb1	1.8687 (19)
C11—H11B	0.9900	F7—Sb2	1.8613 (18)
C12—N3	1.268 (4)	F8—Sb2	1.855 (2)
C12—O3	1.343 (4)	F9—Sb2	1.832 (2)
C12—C13	1.503 (5)	F10—Sb2	1.863 (2)
C13—C16	1.504 (4)	F11—Sb2	1.844 (2)
C13—C15	1.536 (4)	F12—Sb2	1.828 (2)
O1—C1—N1	125.7 (3)	H17A—C17—H17B	109.0
O1—C1—H1	117.1	N4—C18—C17	101.4 (2)
N1—C1—H1	117.1	N4—C18—C19	110.0 (3)
N1—C2—H2A	109.5	C17—C18—C19	115.8 (3)
N1—C2—H2B	109.5	N4—C18—H18	109.7
H2A—C2—H2B	109.5	C17—C18—H18	109.7
N1—C2—H2C	109.5	C19—C18—H18	109.7
H2A—C2—H2C	109.5	C20—C19—C18	113.5 (3)
H2B—C2—H2C	109.5	C20—C19—C21	111.4 (3)
N1—C3—H3A	109.5	C18—C19—C21	110.4 (3)
N1—C3—H3B	109.5	C20—C19—H19	107.1
H3A—C3—H3B	109.5	C18—C19—H19	107.1
N1—C3—H3C	109.5	C21—C19—H19	107.1
H3A—C3—H3C	109.5	C19—C20—H20A	109.5
H3B—C3—H3C	109.5	C19—C20—H20B	109.5
O2—C4—N2	123.9 (3)	H20A—C20—H20B	109.5
O2—C4—H4	118.1	C19—C20—H20C	109.5
N2—C4—H4	118.1	H20A—C20—H20C	109.5
N2—C5—H5A	109.5	H20B—C20—H20C	109.5
N2—C5—H5B	109.5	C19—C21—H21A	109.5
H5A—C5—H5B	109.5	C19—C21—H21B	109.5
N2—C5—H5C	109.5	H21A—C21—H21B	109.5
H5A—C5—H5C	109.5	C19—C21—H21C	109.5
H5B—C5—H5C	109.5	H21A—C21—H21C	109.5
N2—C6—H6A	109.5	H21B—C21—H21C	109.5
N2—C6—H6B	109.5	O2—Cu—N4	179.10 (10)
H6A—C6—H6B	109.5	O2—Cu—O1	89.32 (9)
N2—C6—H6C	109.5	N4—Cu—O1	89.90 (9)
H6A—C6—H6C	109.5	O2—Cu—N3	89.86 (10)
H6B—C6—H6C	109.5	N4—Cu—N3	90.92 (10)
C10—C7—C8	114.1 (3)	O1—Cu—N3	179.05 (10)
C10—C7—C9	110.1 (3)	O2—Cu—F7	88.26 (8)
C8—C7—C9	110.8 (3)	N4—Cu—F7	92.21 (9)
C10—C7—H7	107.2	O1—Cu—F7	92.32 (8)
C8—C7—H7	107.2	N3—Cu—F7	87.16 (9)
C9—C7—H7	107.2	O2—Cu—F5	87.74 (8)
C7—C8—H8A	109.5	N4—Cu—F5	91.75 (8)
C7—C8—H8B	109.5	O1—Cu—F5	84.92 (8)
H8A—C8—H8B	109.5	N3—Cu—F5	95.54 (8)
C7—C8—H8C	109.5	F7—Cu—F5	175.16 (7)
H8A—C8—H8C	109.5	Sb1—F5—Cu	138.67 (9)
H8B—C8—H8C	109.5	Sb2—F7—Cu	164.27 (12)
C7—C9—H9A	109.5	C1—N1—C2	120.1 (3)
C7—C9—H9B	109.5	C1—N1—C3	123.0 (3)
H9A—C9—H9B	109.5	C2—N1—C3	116.8 (3)
C7—C9—H9C	109.5	C4—N2—C5	120.0 (3)
H9A—C9—H9C	109.5	C4—N2—C6	121.7 (3)
H9B—C9—H9C	109.5	C5—N2—C6	117.9 (3)
N3—C10—C7	110.8 (3)	C12—N3—C10	107.3 (2)
N3—C10—C11	100.4 (2)	C12—N3—Cu	127.3 (2)
C7—C10—C11	115.0 (3)	C10—N3—Cu	125.2 (2)
N3—C10—H10	110.1	C16—N4—C18	107.3 (3)
C7—C10—H10	110.1	C16—N4—Cu	127.6 (2)
C11—C10—H10	110.1	C18—N4—Cu	125.06 (19)
O3—C11—C10	104.2 (2)	C1—O1—Cu	122.6 (2)
O3—C11—H11A	110.9	C4—O2—Cu	123.9 (2)
C10—C11—H11A	110.9	C12—O3—C11	105.4 (2)
O3—C11—H11B	110.9	C16—O4—C17	106.0 (2)
C10—C11—H11B	110.9	F2—Sb1—F3	90.45 (11)
H11A—C11—H11B	108.9	F2—Sb1—F4	177.53 (11)
N3—C12—O3	117.2 (3)	F3—Sb1—F4	90.55 (10)
N3—C12—C13	129.8 (3)	F2—Sb1—F6	88.91 (11)
O3—C12—C13	112.9 (3)	F3—Sb1—F6	178.42 (10)
C12—C13—C16	113.1 (3)	F4—Sb1—F6	90.03 (10)
C12—C13—C15	108.7 (3)	F2—Sb1—F1	91.46 (11)
C16—C13—C15	107.4 (3)	F3—Sb1—F1	91.31 (9)
C12—C13—C14	108.8 (3)	F4—Sb1—F1	90.78 (11)
C16—C13—C14	108.7 (3)	F6—Sb1—F1	90.14 (10)
C15—C13—C14	110.2 (3)	F2—Sb1—F5	88.61 (10)
C13—C14—H14A	109.5	F3—Sb1—F5	88.92 (8)
C13—C14—H14B	109.5	F4—Sb1—F5	89.16 (10)
H14A—C14—H14B	109.5	F6—Sb1—F5	89.63 (9)
C13—C14—H14C	109.5	F1—Sb1—F5	179.76 (10)
H14A—C14—H14C	109.5	F12—Sb2—F9	178.67 (15)
H14B—C14—H14C	109.5	F12—Sb2—F11	88.77 (13)
C13—C15—H15A	109.5	F9—Sb2—F11	91.63 (14)
C13—C15—H15B	109.5	F12—Sb2—F8	91.47 (13)
H15A—C15—H15B	109.5	F9—Sb2—F8	88.12 (14)
C13—C15—H15C	109.5	F11—Sb2—F8	179.62 (12)
H15A—C15—H15C	109.5	F12—Sb2—F7	90.88 (11)
H15B—C15—H15C	109.5	F9—Sb2—F7	87.85 (12)
N4—C16—O4	117.1 (3)	F11—Sb2—F7	89.62 (11)
N4—C16—C13	129.4 (3)	F8—Sb2—F7	90.09 (10)
O4—C16—C13	113.5 (3)	F12—Sb2—F10	89.71 (13)
O4—C17—C18	103.9 (2)	F9—Sb2—F10	91.55 (14)
O4—C17—H17A	111.0	F11—Sb2—F10	91.94 (12)
C18—C17—H17A	111.0	F8—Sb2—F10	88.36 (12)
O4—C17—H17B	111.0	F7—Sb2—F10	178.35 (11)
C18—C17—H17B	111.0
C8—C7—C10—N3	59.8 (3)	F7—Cu—N3—C12	97.1 (3)
C9—C7—C10—N3	−174.9 (3)	F5—Cu—N3—C12	−86.9 (3)
C8—C7—C10—C11	−53.1 (4)	O2—Cu—N3—C10	0.8 (2)
C9—C7—C10—C11	72.1 (4)	N4—Cu—N3—C10	−179.7 (2)
N3—C10—C11—O3	−22.7 (3)	F7—Cu—N3—C10	−87.5 (2)
C7—C10—C11—O3	96.3 (3)	F5—Cu—N3—C10	88.5 (2)
N3—C12—C13—C16	9.9 (5)	O4—C16—N4—C18	−8.3 (4)
O3—C12—C13—C16	−173.6 (3)	C13—C16—N4—C18	169.4 (3)
N3—C12—C13—C15	129.1 (4)	O4—C16—N4—Cu	168.4 (2)
O3—C12—C13—C15	−54.4 (4)	C13—C16—N4—Cu	−13.8 (5)
N3—C12—C13—C14	−110.9 (4)	C17—C18—N4—C16	17.6 (3)
O3—C12—C13—C14	65.6 (4)	C19—C18—N4—C16	−105.6 (3)
C12—C13—C16—N4	5.2 (5)	C17—C18—N4—Cu	−159.3 (2)
C15—C13—C16—N4	−114.8 (4)	C19—C18—N4—Cu	77.5 (3)
C14—C13—C16—N4	126.0 (4)	O1—Cu—N4—C16	−171.4 (3)
C12—C13—C16—O4	−177.0 (3)	N3—Cu—N4—C16	8.1 (3)
C15—C13—C16—O4	63.0 (4)	F7—Cu—N4—C16	−79.1 (3)
C14—C13—C16—O4	−56.2 (4)	F5—Cu—N4—C16	103.7 (3)
O4—C17—C18—N4	−20.0 (3)	O1—Cu—N4—C18	4.8 (2)
O4—C17—C18—C19	99.0 (3)	N3—Cu—N4—C18	−175.7 (2)
N4—C18—C19—C20	59.9 (4)	F7—Cu—N4—C18	97.1 (2)
C17—C18—C19—C20	−54.3 (4)	F5—Cu—N4—C18	−80.1 (2)
N4—C18—C19—C21	−174.2 (3)	N1—C1—O1—Cu	−169.4 (3)
C17—C18—C19—C21	71.6 (4)	O2—Cu—O1—C1	−61.1 (3)
O2—Cu—F5—Sb1	62.36 (16)	N4—Cu—O1—C1	119.4 (3)
N4—Cu—F5—Sb1	−118.37 (16)	F7—Cu—O1—C1	27.2 (3)
O1—Cu—F5—Sb1	151.89 (16)	F5—Cu—O1—C1	−148.9 (3)
N3—Cu—F5—Sb1	−27.28 (17)	N2—C4—O2—Cu	−168.2 (2)
O2—Cu—F7—Sb2	106.6 (4)	O1—Cu—O2—C4	−50.1 (2)
N4—Cu—F7—Sb2	−72.7 (4)	N3—Cu—O2—C4	130.4 (3)
O1—Cu—F7—Sb2	17.3 (4)	F7—Cu—O2—C4	−142.4 (3)
N3—Cu—F7—Sb2	−163.5 (4)	F5—Cu—O2—C4	34.9 (2)
O1—C1—N1—C2	−0.3 (5)	N3—C12—O3—C11	−9.1 (4)
O1—C1—N1—C3	179.5 (3)	C13—C12—O3—C11	173.9 (3)
O2—C4—N2—C5	3.6 (5)	C10—C11—O3—C12	20.0 (3)
O2—C4—N2—C6	176.4 (3)	N4—C16—O4—C17	−5.6 (4)
O3—C12—N3—C10	−6.7 (4)	C13—C16—O4—C17	176.3 (3)
C13—C12—N3—C10	169.7 (3)	C18—C17—O4—C16	16.4 (3)
O3—C12—N3—Cu	169.3 (2)	Cu—F5—Sb1—F2	−116.14 (16)
C13—C12—N3—Cu	−14.2 (5)	Cu—F5—Sb1—F3	−25.67 (15)
C7—C10—N3—C12	−103.8 (3)	Cu—F5—Sb1—F4	64.90 (15)
C11—C10—N3—C12	18.2 (3)	Cu—F5—Sb1—F6	154.94 (15)
C7—C10—N3—Cu	80.0 (3)	Cu—F7—Sb2—F12	−145.8 (4)
C11—C10—N3—Cu	−158.0 (2)	Cu—F7—Sb2—F9	33.8 (4)
O2—Cu—N3—C12	−174.6 (3)	Cu—F7—Sb2—F11	125.5 (4)
N4—Cu—N3—C12	4.9 (3)	Cu—F7—Sb2—F8	−54.3 (4)

Table 1

Selected geometric parameters (Å, °)

Cu—O2	1.951 (2)
Cu—N4	1.962 (2)
Cu—O1	1.964 (2)
Cu—N3	1.971 (2)
Cu—F7	2.4232 (18)
Cu—F5	2.5452 (19)