trans-Bis(1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionato-κO,O')bis-(4-methyl-1,2,3-selenadiazole-κN)copper(II).

In the title compound, [Cu(C(5)HF(6)O(2))(2)(C(3)H(4)N(2)Se)(2)], the Cu(II) atom (site symmetry ) is coordinated by two O,O'-bidentate 1,1,1,5,5,5-hexa-fluoro-2,4-penta-nedione (hp) ligands and two 4-methyl-1,2,3-selenadiazole mol-ecules, resulting in a slightly distorted trans-CuN(2)O(4) octa-hedral geometry in which the cis angles deviate by less than 3° from 90°. The selenadiazole plane is canted at 73.13 (17)° to the square plane defined by the penta-nedionate O atoms. The F atoms of one of the hp ligands are disordered over two sets of sites in a 0.66 (3):0.34 (3) ratio. There are no significant inter-molecular inter-actions in the crystal.

Related literature

Similar stuctures are exhibited by bis­(hexa­fluoro­penta­dionato) copper complexes of imidazole (Colacio et al., 2000 ▶), pyrazole (Kogane et al., 1990 ▶; Fokin et al., 2002 ▶) and substituted pyridines (De Panthou et al., 1996 ▶; Iwahori et al., 2001 ▶; Sano et al., 1997 ▶).

Experimental

Crystal data

[Cu(C5HF6O2)2(C3H4N2Se)2]

M = 771.74

Monoclinic,

a = 8.191 (2) Å

b = 14.390 (4) Å

c = 11.429 (4) Å

β = 104.86 (3)°

V = 1302.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 3.75 mm−1

T = 293 K

0.25 × 0.25 × 0.25 mm

Data collection

Nicolet R3m/V diffractometer

Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008 ▶) T min = 0.755, T max = 0.793

3218 measured reflections

3014 independent reflections

1894 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.126

S = 1.03

3014 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.42 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXL97 (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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001297/hb5239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001297/hb5239Isup2.hkl

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

[Cu(C5HF6O2)2(C3H4N2Se)2]	Dx = 1.968 Mg m−3
Mr = 771.74	Melting point: 355 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.191 (2) Å	Cell parameters from 20 reflections
b = 14.390 (4) Å	θ = 7.9–14.5°
c = 11.429 (4) Å	µ = 3.75 mm−1
β = 104.86 (3)°	T = 293 K
V = 1302.1 (7) Å3	Parallelpiped, green
Z = 2	0.25 × 0.25 × 0.25 mm
F(000) = 742

Nicolet R3m/V diffractometer	Rint = 0.048
graphite	θmax = 27.6°, θmin = 2.3°
profile data from θ/2θ scans	h = −2→10
Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008)	k = −6→18
Tmin = 0.755, Tmax = 0.793	l = −14→14
3218 measured reflections	3 standard reflections every 97 reflections
3014 independent reflections	intensity decay: none
1894 reflections with I > 2σ(I)

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0459P)2 + 1.964P] where P = (Fo2 + 2Fc2)/3
3014 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu	0.0000	0.0000	0.5000	0.0467 (2)
Se	0.11516 (8)	0.14840 (4)	0.26686 (5)	0.0667 (2)
N1	0.0700 (6)	0.1433 (3)	0.4188 (4)	0.0564 (11)
N2	0.0391 (6)	0.2234 (3)	0.4541 (4)	0.0572 (11)
C6	0.0853 (8)	0.2732 (4)	0.2739 (5)	0.0628 (15)
C7	0.0470 (7)	0.2966 (4)	0.3777 (5)	0.0577 (13)
C71	0.0087 (11)	0.3911 (4)	0.4164 (6)	0.093 (2)
H71A	−0.0143	0.4322	0.3479	0.140*
H71B	0.1040	0.4139	0.4772	0.140*
H71C	−0.0881	0.3882	0.4489	0.140*
O1	−0.1707 (5)	−0.0178 (2)	0.3457 (3)	0.0546 (9)
O2	−0.1614 (5)	0.0692 (2)	0.5702 (3)	0.0520 (8)
C1	−0.3071 (7)	0.0274 (4)	0.3148 (5)	0.0582 (14)
C11	−0.4037 (9)	0.0109 (5)	0.1836 (6)	0.0771 (19)
F11	−0.5552 (6)	0.0472 (5)	0.1545 (4)	0.157 (3)
F12	−0.3218 (6)	0.0490 (3)	0.1084 (3)	0.1142 (15)
F13	−0.4170 (6)	−0.0780 (3)	0.1545 (4)	0.1076 (14)
C2	−0.3728 (8)	0.0879 (4)	0.3859 (5)	0.0674 (16)
C3	−0.2960 (7)	0.1034 (4)	0.5075 (5)	0.0541 (13)
C31	−0.3885 (10)	0.1722 (5)	0.5750 (7)	0.0782 (19)
F311	−0.318 (2)	0.2515 (8)	0.581 (3)	0.145 (9)	0.66 (3)
F312	−0.5418 (12)	0.1700 (18)	0.5425 (19)	0.161 (10)	0.66 (3)
F313	−0.349 (2)	0.1452 (18)	0.6957 (10)	0.137 (6)	0.66 (3)
F321	−0.300 (2)	0.210 (2)	0.663 (3)	0.105 (10)	0.34 (3)
F322	−0.520 (6)	0.141 (2)	0.591 (5)	0.18 (2)	0.34 (3)
F323	−0.457 (6)	0.2452 (19)	0.4941 (19)	0.138 (14)	0.34 (3)
H2	−0.475 (7)	0.118 (4)	0.347 (5)	0.065 (17)*
H6	0.085 (9)	0.314 (5)	0.207 (7)	0.12 (3)*

	U11	U22	U33	U12	U13	U23
Cu	0.0603 (5)	0.0401 (4)	0.0375 (4)	0.0048 (4)	0.0085 (4)	−0.0043 (4)
Se	0.0834 (5)	0.0652 (4)	0.0568 (4)	0.0044 (3)	0.0276 (3)	−0.0066 (3)
N1	0.072 (3)	0.051 (3)	0.051 (2)	0.001 (2)	0.023 (2)	0.004 (2)
N2	0.081 (3)	0.047 (3)	0.047 (2)	0.002 (2)	0.023 (2)	0.005 (2)
C6	0.080 (4)	0.063 (4)	0.049 (3)	−0.001 (3)	0.022 (3)	0.012 (3)
C7	0.080 (4)	0.047 (3)	0.046 (3)	0.002 (3)	0.014 (3)	0.009 (2)
C71	0.152 (7)	0.059 (4)	0.076 (4)	0.002 (4)	0.044 (5)	0.001 (3)
O1	0.065 (2)	0.051 (2)	0.0436 (18)	0.0042 (18)	0.0060 (17)	−0.0060 (16)
O2	0.064 (2)	0.047 (2)	0.0444 (18)	0.0014 (17)	0.0132 (17)	−0.0044 (15)
C1	0.067 (4)	0.058 (3)	0.045 (3)	0.003 (3)	0.007 (3)	−0.002 (2)
C11	0.077 (4)	0.092 (5)	0.052 (4)	0.012 (4)	−0.003 (3)	−0.016 (3)
F11	0.098 (3)	0.260 (7)	0.081 (3)	0.080 (4)	−0.033 (2)	−0.062 (4)
F12	0.149 (4)	0.133 (4)	0.052 (2)	−0.001 (3)	0.011 (2)	0.013 (2)
F13	0.130 (4)	0.102 (3)	0.072 (2)	−0.014 (3)	−0.008 (2)	−0.024 (2)
C2	0.061 (4)	0.074 (4)	0.060 (3)	0.013 (3)	0.003 (3)	−0.014 (3)
C3	0.056 (3)	0.048 (3)	0.061 (3)	−0.001 (3)	0.019 (3)	−0.010 (3)
C31	0.081 (5)	0.070 (5)	0.089 (5)	−0.002 (4)	0.032 (4)	−0.030 (4)
F311	0.164 (16)	0.064 (6)	0.23 (2)	0.004 (7)	0.095 (18)	−0.043 (9)
F312	0.045 (6)	0.27 (2)	0.158 (13)	0.041 (8)	−0.001 (6)	−0.123 (14)
F313	0.147 (12)	0.188 (15)	0.088 (6)	0.053 (10)	0.052 (7)	−0.030 (8)
F321	0.067 (11)	0.12 (2)	0.104 (17)	0.027 (14)	−0.015 (11)	−0.071 (14)
F322	0.23 (4)	0.132 (17)	0.27 (5)	−0.10 (2)	0.22 (4)	−0.10 (2)
F323	0.21 (3)	0.101 (14)	0.094 (12)	0.105 (18)	0.034 (16)	0.019 (10)

Cu—O1	1.967 (3)	C1—C2	1.390 (8)
Cu—O2	1.981 (3)	C1—C11	1.524 (8)
Cu—N1	2.391 (4)	C11—F11	1.308 (7)
Se—C6	1.817 (6)	C11—F13	1.318 (8)
Se—N1	1.867 (4)	C11—F12	1.336 (8)
N1—N2	1.268 (6)	C2—C3	1.389 (8)
N2—C7	1.380 (6)	C2—H2	0.95 (6)
C6—C7	1.345 (7)	C3—C31	1.565 (8)
C6—H6	0.97 (8)	C31—F312	1.214 (12)
C7—C71	1.488 (8)	C31—F311	1.273 (12)
C71—H71A	0.96	C31—F313	1.389 (15)
C71—H71B	0.96	C31—F321	1.204 (17)
C71—H71C	0.96	C31—F322	1.23 (2)
O1—C1	1.262 (6)	C31—F323	1.418 (17)
O2—C3	1.252 (6)
O1—Cu—O2i	88.06 (14)	O1—C1—C11	113.2 (5)
O1—Cu—O2	91.94 (14)	C2—C1—C11	119.5 (5)
O1—Cu—N1	87.15 (15)	F11—C11—F13	108.2 (6)
O1i—Cu—N1	92.85 (15)	F11—C11—F12	105.9 (6)
O2i—Cu—N1	91.44 (15)	F13—C11—F12	105.0 (6)
O2—Cu—N1	88.57 (15)	F11—C11—C1	114.0 (5)
C6—Se—N1	86.4 (2)	F13—C11—C1	112.8 (6)
N2—N1—Se	111.3 (3)	F12—C11—C1	110.4 (6)
N2—N1—Cu	125.0 (3)	C3—C2—C1	122.8 (6)
Se—N1—Cu	121.3 (2)	C3—C2—H2	121 (3)
N1—N2—C7	116.6 (4)	C1—C2—H2	116 (3)
C7—C6—Se	110.6 (4)	O2—C3—C2	128.1 (5)
C7—C6—H6	126 (4)	O2—C3—C31	115.7 (5)
Se—C6—H6	123 (4)	C2—C3—C31	116.3 (6)
C6—C7—N2	115.2 (5)	F312—C31—F311	117.2 (13)
C6—C7—C71	127.2 (5)	F312—C31—F313	104.9 (12)
N2—C7—C71	117.5 (5)	F311—C31—F313	102.0 (11)
C7—C71—H71A	109.5	F312—C31—C3	115.2 (8)
C7—C71—H71B	109.5	F311—C31—C3	109.0 (8)
H71A—C71—H71B	109.5	F313—C31—C3	107.1 (8)
C7—C71—H71C	109.5	F321—C31—F322	114 (2)
H71A—C71—H71C	109.5	F321—C31—F323	105.4 (16)
H71B—C71—H71C	109.5	F322—C31—F323	99 (2)
C1—O1—Cu	123.9 (3)	F321—C31—C3	115.3 (10)
C3—O2—Cu	123.2 (3)	F322—C31—C3	113.4 (14)
O1—C1—C2	127.4 (5)	F323—C31—C3	107.9 (9)
C6—Se—N1—N2	0.8 (4)	Cu—O1—C1—C11	171.1 (4)
C6—Se—N1—Cu	164.0 (3)	O1—C1—C11—F11	171.4 (6)
O1—Cu—N1—N2	109.9 (4)	C2—C1—C11—F11	−8.8 (10)
O1i—Cu—N1—N2	−70.1 (4)	O1—C1—C11—F13	47.5 (8)
O2i—Cu—N1—N2	−162.1 (4)	C2—C1—C11—F13	−132.7 (6)
O2—Cu—N1—N2	17.9 (4)	O1—C1—C11—F12	−69.6 (7)
O1—Cu—N1—Se	−50.9 (3)	C2—C1—C11—F12	110.2 (7)
O1i—Cu—N1—Se	129.1 (3)	O1—C1—C2—C3	−3.2 (11)
O2i—Cu—N1—Se	37.1 (3)	C11—C1—C2—C3	177.1 (6)
O2—Cu—N1—Se	−142.9 (3)	Cu—O2—C3—C2	11.9 (8)
Se—N1—N2—C7	−1.0 (6)	Cu—O2—C3—C31	−168.1 (4)
Cu—N1—N2—C7	−163.4 (4)	C1—C2—C3—O2	1.3 (10)
N1—Se—C6—C7	−0.5 (5)	C1—C2—C3—C31	−178.8 (6)
Se—C6—C7—N2	0.1 (7)	O2—C3—C31—F312	−145.3 (18)
Se—C6—C7—C71	−178.2 (6)	C2—C3—C31—F312	34.8 (19)
N1—N2—C7—C6	0.6 (8)	O2—C3—C31—F311	80.6 (17)
N1—N2—C7—C71	179.1 (6)	C2—C3—C31—F311	−99.4 (16)
O2i—Cu—O1—C1	−164.5 (4)	O2—C3—C31—F313	−29.0 (14)
O2—Cu—O1—C1	15.5 (4)	C2—C3—C31—F313	151.0 (13)
N1i—Cu—O1—C1	107.0 (4)	O2—C3—C31—F321	24 (3)
N1—Cu—O1—C1	−73.0 (4)	C2—C3—C31—F321	−156 (3)
O1—Cu—O2—C3	−16.9 (4)	O2—C3—C31—F322	−110 (3)
O1i—Cu—O2—C3	163.1 (4)	C2—C3—C31—F322	71 (3)
N1i—Cu—O2—C3	−109.8 (4)	O2—C3—C31—F323	142 (2)
N1—Cu—O2—C3	70.2 (4)	C2—C3—C31—F323	−38 (3)
Cu—O1—C1—C2	−8.6 (8)

Table 1

Selected bond lengths (Å)

Cu—O1	1.967 (3)
Cu—O2	1.981 (3)
Cu—N1	2.391 (4)