Bis(μ-4-phenyl­pyridine N-oxide-κ2O:O)bis­[bis­(1,1,1,5,5,5-hexa­fluoro­pentane-2,4-dionato)copper(II)]

Ramos, A.I.; Fernandes, J.A.; Silva, P.; Ribeiro-Claro, P.J.A.; Braga, S.S.; Almeida Paz, F.A.

doi:10.1107/S1600536810022567

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages m824-m825

doi:10.1107/S1600536810022567

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Bis(μ-4-phenylpyridine N-oxide-κ²O:O)bis[bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato)copper(II)]

Ana I. Ramos,^a José A. Fernandes,^a Patrícia Silva,^a Paulo J. A. Ribeiro-Claro,^a Susana S. Braga ^a and Filipe A. Almeida Paz ^a ^*

^aDepartment of Chemistry, CICECO, University of Aveiro, 3810-193 Aveiro, Portugal
^*Correspondence e-mail: filipe.paz@ua.pt

(Received 9 June 2010; accepted 12 June 2010; online 23 June 2010)

The asymmetric unit of the title compound, [Cu₂(C₅HF₆O₂)₄(C₁₁H₉NO)₂], contains one half of the centrosymmetric dinuclear complex. The coordination geometry of the Cu^II atom is octahedral, exhibiting a typical Jahn–Teller distortion. One trifluoromethyl group is rotationally disordered between two orientations in a 1:1 ratio.

Related literature

For the use of copper complexes in optical devices, see: Akkılıç et al. (2010 ); Armaroli et al. (2007 ); Bessho et al. (2008 ); Chan et al. (2010 ); Daniel et al. (2009 ); Jeon et al. (2008 ); Kambayashi et al. (2005 ); Peranantham et al. (2007 ); Si et al. (2008 ); Vogler & Kunkely (2001 ); Walsh et al. (2009 ). For related complexes with 4-phenylpyridine-N-oxide, see: Papadaki et al. (1999 ); Watson & Johnson (1971 ). For general background to studies on copper complexes from our research group, see: Fernandes et al. (2010 ); Shi et al. (2006 ); Paz et al. (2005 ); Girginova et al. (2005 ); Brandão et al. (2005 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Cu₂(C₅HF₆O₂)₄(C₁₁H₉NO)₂]
M_r = 1297.70
Triclinic, $[P \overline 1]$
a = 10.3830 (4) Å
b = 10.7870 (4) Å
c = 11.2498 (4) Å
α = 99.055 (2)°
β = 99.036 (2)°
γ = 98.258 (2)°
V = 1210.40 (8) Å³
Z = 1
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 150 K
0.18 × 0.10 × 0.09 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.836, T_max = 0.913
47759 measured reflections
6427 independent reflections
5461 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.04
6427 reflections
397 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 1.21 e Å⁻³
Δρ_min = −1.40 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT-Plus (Bruker, 2005 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022567/cv2732sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022567/cv2732Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of 4-phenylpyridine-N-oxide (PPNO; C₁₁H₉NO) is rather unknown. Surveying the Cambridge Structural Database (Allen, 2002) only two coordination compounds were found, namely a copper (Watson & Johnson, 1971) and a tin compound (Papadaki et al., 1999).

The title compound, [Cu(C₅HF₆O₂)₂(C₁₁H₉NO)₂] (I) (where C₅HF₆O₂^- is hexafluoroacetylacetonate and C₁₁H₉NO corresponds to 4-phenylpyridine-N-oxide), has a bright green colour which is of interest for the potential use as a dye in several applications, such as in organic electronics. Coloured materials, including metal coordination compounds, have been explored in the last decades because pigmentation is a strong indicative of promising physical and optical properties (Vogler & Kunkely, 2001). Recent applications of copper coordination complexes include a Schottky diode based on a macrocyclic binuclear Cu²⁺ complex (Akkılıç et al., 2010) and a series of Graetzel solar cells using 6,6'-dimethyl-dicarboxylated-bipyridine complexes (Bessho et al., 2008). The use of Cu²⁺ complexes in OLEDs is still limited (Armaroli et al., 2007), and emission still relies mostly on Cu⁺ complexes, such as [Cu(I)bis(triphenylphosphine)dipyridophenazine] (Walsh et al., 2009) and three Cu(I)pyridylbenzimidazole complexes (Si et al., 2008). In addition, copper complexes are advantageous from the technological processing perspective, adaptable to various film deposition techniques: molecular beam epitaxy (Kambayashi et al., 2005), vacuum evaporation (Peranantham et al., 2007), electrodeposition (Chan et al., 2010) and chemical vapour deposition (CVD), either plasma-enhanced (Daniel et al., 2009) or the widespread metal organic CVD (Jeon et al., 2008).

Following our interest in the preparation and study of the properties of copper compounds (Fernandes et al., 2010; Shi et al., 2006; Paz et al., 2005; Girginova et al., 2005; Brandão et al., 2005) we have reacted [Cu(hfac)₂] (where hfac^- stands for hexafluoroacetylacetonate) with PPNO, affording the title compound as a vivid green crystalline material, whose crystal structure we report herein.

The structure is dimeric having a point of inversion in the geometrical centre of the quadrangle defined by Cu1···O5···Cu1⁽ⁱ⁾···O5⁽ⁱ⁾ (Figure 1) [symmetry code: (i) 2 - x, -y, -z]. The asymmetric unit contains one PPNO ligand and one [Cu(hfac)₂] moiety. The atoms Cu1, O2, O4 and O5, and their symmetry-related counterparts [symmetry code (i)], form a plane (longest distance to the average plane of about 0.041 Å). Likewise, atoms Cu1, O1 and O3, and their symmetry-related counterparts [symmetry code (i)], define a second plane (longest distance to this average plane of about 0.048 Å), which is perpendicular to the previous one. The Cu²⁺ centre exhibits a typical octahedral coordination environment with a strong Jahn-Teller distortion: the Cu—O bonds (equatorial plane) range from 1.9500 (19) to 1.9751 (18) Å, while the Cu—O bonds (at apical positions) are either 2.251 (2) or 2.4427 (18) Å. With the exception of the angles O5—Cu1—O5⁽ⁱ⁾ [76.90 (7)°] and O2—Cu1—O4 [101.08 (8)°], the cis octahedral angles fall within a rather short range around the ideal value: 84.55 (7)–97.37 (8)° (Table 1). The trans octahedral angles are between 161.06 (8)° and 174.96 (8)°. The two average planes containing the aromatic rings of PPNO are mutually rotated by ca 37°. The structure exhibits crystallographic disorder associated with the fluorine atoms F4, F5 and F6 (rates of occupancy 50% for each location). Noteworthy, symmetry-related copper complexes are located at the vertex of the unit cell (Figure 2), with the inner space being essentially occupied by the coordinated organic ligands, leading to a hydrophobic empty space of about 36 Å³.

Related literature top

For the use of copper complexes in optical devices, see: Akkılıç et al. (2010); Armaroli et al. (2007); Bessho et al. (2008); Chan et al. (2010); Daniel et al. (2009); Jeon et al. (2008); Kambayashi et al. (2005); Peranantham et al. (2007); Si et al. (2008) Vogler & Kunkely (2001); Walsh et al. (2009). For related complexes with 4-phenylpyridine-N-oxide, see: Papadaki et al. (1999); Watson & Johnson (1971). For general background to studies on copper complexes from our research group, see: Fernandes et al. (2010); Shi et al. (2006); Paz et al. (2005); Girginova et al. (2005); Brandão et al. (2005). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Chemicals were purchased from commercial sources and were used as received without purification.

4-Phenylpyridine-N-oxide (PPNO, 71.7 mg, 0.419 mmol, Aldrich) was slowly added to a previously-prepared [Cu(hfac)₂] (100.0 mg, 0.209 mmol; hfac^- stands for hexafluoroacetylacetonate) solution in 10 ml of acetone. The resulting solution was magnetically stirred at 30 °C for 30 minutes. By slow evaporation to dryness, a green solid was obtained, which was dissolved in ethanol, gravity filtered and deposited above a water layer. Green crystals of the title compound formed after two days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Schematic representation, in ball-and-stick and polyhedral fashions, of the molecular structure of the title compound. The crystallographic disorder associated with the —CF₃ group was omitted for simplicity. Symmetry code: (i) 2 - x, -y, -z.
	Fig. 2. Perspective view along the c axis of the unit cell of the crystal packing of the title compound.

Bis(µ-4-phenylpyridine N-oxide-κ²O:O)bis[bis(1,1,1,5,5,5- hexafluoropentane-2,4-dionato)copper(II)] top

Crystal data top

[Cu₂(C₅HF₆O₂)₄(C₁₁H₉NO)₂]	Z = 1
M_r = 1297.70	F(000) = 642
Triclinic, P1	D_x = 1.780 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3830 (4) Å	Cell parameters from 9842 reflections
b = 10.7870 (4) Å	θ = 2.9–28.6°
c = 11.2498 (4) Å	µ = 1.03 mm⁻¹
α = 99.055 (2)°	T = 150 K
β = 99.036 (2)°	Block, green
γ = 98.258 (2)°	0.18 × 0.10 × 0.09 mm
V = 1210.40 (8) Å³

Data collection top

Bruker X8 Kappa CCD APEXII diffractometer	6427 independent reflections
Radiation source: fine-focus sealed tube	5461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω/phi scans	θ_max = 29.1°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
T_min = 0.836, T_max = 0.913	k = −14→14
47759 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0712P)² + 2.0571P] where P = (F_o² + 2F_c²)/3
6427 reflections	(Δ/σ)_max = 0.003
397 parameters	Δρ_max = 1.21 e Å⁻³
24 restraints	Δρ_min = −1.40 e Å⁻³

Crystal data top

[Cu₂(C₅HF₆O₂)₄(C₁₁H₉NO)₂]	γ = 98.258 (2)°
M_r = 1297.70	V = 1210.40 (8) Å³
Triclinic, P1	Z = 1
a = 10.3830 (4) Å	Mo Kα radiation
b = 10.7870 (4) Å	µ = 1.03 mm⁻¹
c = 11.2498 (4) Å	T = 150 K
α = 99.055 (2)°	0.18 × 0.10 × 0.09 mm
β = 99.036 (2)°

Data collection top

Bruker X8 Kappa CCD APEXII diffractometer	6427 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	5461 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.913	R_int = 0.029
47759 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	24 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	Δρ_max = 1.21 e Å⁻³
6427 reflections	Δρ_min = −1.40 e Å⁻³
397 parameters

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)
Cu1	1.01536 (3)	0.13209 (3)	−0.07044 (3)	0.02205 (10)
O1	1.17596 (17)	0.20733 (17)	0.05247 (16)	0.0235 (4)
O2	1.12021 (19)	0.2109 (2)	−0.21003 (18)	0.0312 (4)
O3	0.86603 (19)	0.05900 (18)	−0.20302 (18)	0.0284 (4)
O4	0.93026 (17)	0.27435 (17)	−0.01281 (18)	0.0255 (4)
O5	0.91578 (18)	0.02993 (17)	0.08021 (16)	0.0238 (4)
N1	0.8997 (2)	0.0995 (2)	0.18579 (19)	0.0217 (4)
C1	1.4020 (2)	0.2518 (2)	0.14122 (18)	0.0382 (7)
C2	1.2903 (2)	0.2335 (2)	0.0291 (2)	0.0227 (5)
C3	1.3311 (3)	0.2502 (3)	−0.0794 (2)	0.0273 (5)
H3	1.4233	0.2686	−0.0795	0.033*
C4	1.2419 (3)	0.2411 (3)	−0.1900 (2)	0.0261 (5)
C5	1.3046 (2)	0.2749 (3)	−0.2985 (2)	0.0426 (7)
C6	0.6641 (2)	0.03964 (18)	−0.3416 (2)	0.0404 (7)
C7	0.7645 (3)	0.1076 (3)	−0.2257 (2)	0.0272 (5)
C8	0.7299 (3)	0.2135 (3)	−0.1602 (3)	0.0329 (6)
H8	0.6459	0.2359	−0.1852	0.039*
C9	0.8158 (2)	0.2876 (2)	−0.0585 (2)	0.0247 (5)
C10	0.7717 (3)	0.4038 (3)	0.0107 (3)	0.0303 (6)
C11	1.0036 (3)	0.1754 (3)	0.2619 (2)	0.0272 (5)
H11	1.0903	0.1761	0.2446	0.033*
C12	0.9841 (3)	0.2522 (3)	0.3650 (2)	0.0261 (5)
H12	1.0580	0.3048	0.4192	0.031*
C13	0.8573 (2)	0.2537 (2)	0.3912 (2)	0.0214 (4)
C14	0.7527 (2)	0.1713 (3)	0.3101 (2)	0.0256 (5)
H14	0.6651	0.1677	0.3258	0.031*
C15	0.7754 (2)	0.0959 (2)	0.2086 (2)	0.0249 (5)
H15	0.7035	0.0408	0.1539	0.030*
C16	0.8344 (2)	0.3403 (2)	0.4986 (2)	0.0228 (5)
C17	0.9250 (3)	0.3653 (3)	0.6087 (2)	0.0299 (5)
H17	1.0018	0.3265	0.6148	0.036*
C18	0.9035 (3)	0.4465 (3)	0.7091 (3)	0.0356 (6)
H18	0.9657	0.4631	0.7837	0.043*
C19	0.7924 (3)	0.5035 (3)	0.7018 (3)	0.0365 (6)
H19	0.7783	0.5591	0.7711	0.044*
C20	0.7019 (3)	0.4793 (3)	0.5936 (3)	0.0398 (7)
H20	0.6254	0.5185	0.5884	0.048*
C21	0.7225 (3)	0.3976 (3)	0.4916 (3)	0.0325 (6)
H21	0.6598	0.3811	0.4173	0.039*
F1	1.36023 (19)	0.2437 (2)	0.24323 (16)	0.0546 (6)
F2	1.4801 (3)	0.3614 (3)	0.1595 (2)	0.1153 (16)
F3	1.4749 (3)	0.1648 (3)	0.1247 (2)	0.150 (2)
F4	1.3541 (8)	0.3951 (3)	−0.2833 (5)	0.122 (4)	0.50
F5	1.4012 (5)	0.2125 (7)	−0.3118 (5)	0.084 (3)	0.50
F6	1.2224 (4)	0.2467 (7)	−0.4024 (3)	0.0588 (17)	0.50
F4'	1.2595 (7)	0.3725 (7)	−0.3328 (9)	0.109 (4)	0.50
F5'	1.4329 (2)	0.3025 (8)	−0.2815 (7)	0.098 (4)	0.50
F6'	1.2680 (10)	0.1810 (7)	−0.3909 (6)	0.199 (8)	0.50
F7	0.7002 (2)	−0.0620 (2)	−0.3950 (2)	0.0803 (9)
F8	0.6504 (3)	0.1140 (2)	−0.4212 (2)	0.0945 (12)
F9	0.54684 (19)	0.0040 (2)	−0.3187 (2)	0.0723 (8)
F10	0.85443 (17)	0.51032 (16)	0.01099 (18)	0.0366 (4)
F11	0.7719 (2)	0.3931 (2)	0.12708 (19)	0.0483 (5)
F12	0.65074 (17)	0.41987 (19)	−0.0375 (2)	0.0465 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01770 (15)	0.02152 (16)	0.02440 (17)	0.00386 (11)	−0.00051 (11)	0.00057 (11)
O1	0.0194 (8)	0.0263 (9)	0.0232 (8)	0.0029 (7)	0.0011 (6)	0.0031 (7)
O2	0.0260 (9)	0.0402 (11)	0.0265 (9)	0.0039 (8)	−0.0006 (7)	0.0109 (8)
O3	0.0249 (9)	0.0284 (9)	0.0276 (9)	0.0032 (7)	−0.0020 (7)	0.0005 (7)
O4	0.0194 (8)	0.0235 (8)	0.0314 (9)	0.0055 (7)	−0.0009 (7)	0.0023 (7)
O5	0.0282 (9)	0.0230 (8)	0.0208 (8)	0.0081 (7)	0.0062 (7)	0.0007 (6)
N1	0.0212 (9)	0.0218 (9)	0.0222 (10)	0.0047 (8)	0.0049 (8)	0.0026 (8)
C1	0.0215 (12)	0.060 (2)	0.0305 (14)	0.0032 (13)	−0.0010 (11)	0.0098 (13)
C2	0.0196 (10)	0.0218 (11)	0.0250 (12)	0.0052 (9)	−0.0009 (9)	0.0031 (9)
C3	0.0187 (11)	0.0348 (14)	0.0291 (13)	0.0053 (10)	0.0032 (9)	0.0088 (10)
C4	0.0272 (12)	0.0279 (12)	0.0260 (12)	0.0100 (10)	0.0061 (10)	0.0074 (10)
C5	0.0358 (16)	0.065 (2)	0.0313 (15)	0.0122 (15)	0.0082 (12)	0.0154 (15)
C6	0.0387 (16)	0.0369 (16)	0.0368 (16)	−0.0026 (13)	−0.0103 (13)	0.0061 (13)
C7	0.0217 (11)	0.0285 (12)	0.0276 (13)	−0.0030 (10)	−0.0033 (9)	0.0077 (10)
C8	0.0198 (12)	0.0331 (14)	0.0421 (16)	0.0046 (10)	−0.0038 (11)	0.0054 (12)
C9	0.0197 (11)	0.0221 (11)	0.0330 (13)	0.0031 (9)	0.0046 (9)	0.0081 (10)
C10	0.0209 (12)	0.0301 (13)	0.0405 (15)	0.0068 (10)	0.0048 (10)	0.0062 (11)
C11	0.0189 (11)	0.0329 (13)	0.0283 (13)	0.0016 (10)	0.0064 (9)	0.0013 (10)
C12	0.0217 (11)	0.0303 (13)	0.0236 (12)	−0.0002 (10)	0.0041 (9)	0.0008 (10)
C13	0.0215 (11)	0.0227 (11)	0.0208 (11)	0.0045 (9)	0.0043 (9)	0.0049 (9)
C14	0.0180 (11)	0.0312 (13)	0.0268 (12)	0.0053 (9)	0.0039 (9)	0.0022 (10)
C15	0.0185 (11)	0.0270 (12)	0.0267 (12)	0.0034 (9)	0.0011 (9)	0.0008 (10)
C16	0.0240 (11)	0.0237 (11)	0.0202 (11)	0.0025 (9)	0.0047 (9)	0.0036 (9)
C17	0.0266 (13)	0.0378 (14)	0.0242 (12)	0.0063 (11)	0.0033 (10)	0.0033 (11)
C18	0.0371 (15)	0.0429 (16)	0.0214 (13)	0.0002 (13)	0.0017 (11)	−0.0002 (11)
C19	0.0498 (18)	0.0337 (15)	0.0253 (13)	0.0071 (13)	0.0126 (12)	−0.0019 (11)
C20	0.0433 (17)	0.0414 (17)	0.0357 (16)	0.0191 (14)	0.0085 (13)	−0.0012 (13)
C21	0.0330 (14)	0.0362 (14)	0.0270 (13)	0.0135 (12)	0.0007 (11)	0.0003 (11)
F1	0.0415 (11)	0.0933 (18)	0.0272 (9)	0.0156 (11)	−0.0025 (8)	0.0110 (10)
F2	0.084 (2)	0.159 (3)	0.0636 (18)	−0.081 (2)	−0.0360 (15)	0.046 (2)
F3	0.147 (3)	0.261 (5)	0.0483 (15)	0.177 (4)	−0.0346 (18)	−0.029 (2)
F4	0.228 (11)	0.058 (4)	0.073 (5)	−0.050 (5)	0.081 (7)	0.007 (3)
F5	0.048 (3)	0.180 (9)	0.061 (4)	0.065 (4)	0.038 (3)	0.063 (5)
F6	0.035 (2)	0.128 (6)	0.0152 (19)	0.018 (3)	0.0034 (15)	0.016 (3)
F4'	0.070 (4)	0.180 (10)	0.137 (8)	0.059 (5)	0.055 (5)	0.135 (8)
F5'	0.029 (2)	0.201 (10)	0.090 (5)	0.011 (4)	0.018 (3)	0.101 (7)
F6'	0.313 (19)	0.144 (9)	0.111 (8)	−0.082 (10)	0.155 (11)	−0.072 (7)
F7	0.0761 (18)	0.0833 (19)	0.0559 (15)	0.0243 (15)	−0.0267 (13)	−0.0345 (14)
F8	0.128 (3)	0.0745 (18)	0.0489 (14)	−0.0453 (18)	−0.0450 (15)	0.0346 (13)
F9	0.0367 (12)	0.0837 (18)	0.0747 (17)	−0.0197 (12)	−0.0092 (11)	−0.0045 (14)
F10	0.0320 (9)	0.0236 (8)	0.0516 (11)	0.0037 (7)	0.0063 (8)	0.0015 (7)
F11	0.0546 (12)	0.0560 (12)	0.0441 (11)	0.0220 (10)	0.0241 (10)	0.0124 (9)
F12	0.0235 (8)	0.0407 (10)	0.0724 (14)	0.0138 (7)	0.0003 (9)	0.0024 (9)

Geometric parameters (Å, º) top

Cu1—O1	1.9711 (17)	C7—C8	1.383 (4)
Cu1—O2	2.251 (2)	C8—C9	1.390 (4)
Cu1—O3	1.9500 (19)	C8—H8	0.9500
Cu1—O4	1.9524 (18)	C9—C10	1.535 (4)
Cu1—O5	2.4427 (18)	C10—F10	1.331 (3)
Cu1—O5ⁱ	1.9751 (18)	C10—F11	1.332 (4)
O1—C2	1.258 (3)	C10—F12	1.334 (3)
O2—C4	1.234 (3)	C11—C12	1.375 (4)
O3—C7	1.252 (3)	C11—H11	0.9500
O4—C9	1.256 (3)	C12—C13	1.395 (3)
O5—N1	1.349 (3)	C12—H12	0.9500
O5—Cu1ⁱ	1.9751 (18)	C13—C14	1.399 (4)
N1—C11	1.343 (3)	C13—C16	1.479 (3)
N1—C15	1.351 (3)	C14—C15	1.367 (4)
N1—Cu1ⁱ	2.945 (2)	C14—H14	0.9500
C1—F3	1.297 (4)	C15—H15	0.9500
C1—F1	1.300 (3)	C16—C21	1.390 (4)
C1—F2	1.301 (4)	C16—C17	1.396 (4)
C1—C2	1.540 (3)	C17—C18	1.384 (4)
C2—C3	1.383 (4)	C17—H17	0.9500
C3—C4	1.410 (4)	C18—C19	1.381 (5)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.540 (3)	C19—C20	1.380 (5)
C5—F6'	1.2982 (15)	C19—H19	0.9500
C5—F4	1.2985 (15)	C20—C21	1.397 (4)
C5—F6	1.2987 (15)	C20—H20	0.9500
C5—F5'	1.2989 (15)	C21—H21	0.9500
C5—F4'	1.2998 (15)	F4—F4'	1.025 (7)
C5—F5	1.3003 (15)	F4—F5'	1.379 (6)
C6—F7	1.298 (3)	F5—F5'	0.968 (7)
C6—F8	1.298 (3)	F5—F6'	1.485 (7)
C6—F9	1.301 (3)	F6—F6'	0.921 (9)
C6—C7	1.542 (3)	F6—F4'	1.423 (7)

O1—Cu1—O2	87.50 (7)	O3—C7—C6	115.7 (2)
O1—Cu1—O5	91.03 (7)	C8—C7—C6	115.7 (2)
O1—Cu1—O5ⁱ	86.68 (8)	C8—C7—Cu1	94.49 (17)
O2—Cu1—O5	174.17 (7)	C6—C7—Cu1	149.74 (18)
O3—Cu1—O1	174.96 (8)	C7—C8—C9	121.1 (2)
O3—Cu1—O2	87.73 (8)	C7—C8—Cu1	60.54 (14)
O3—Cu1—O4	92.62 (8)	C9—C8—Cu1	60.60 (15)
O3—Cu1—O5	93.57 (7)	C7—C8—H8	119.4
O3—Cu1—O5ⁱ	92.35 (8)	C9—C8—H8	119.4
O4—Cu1—O1	89.86 (8)	Cu1—C8—H8	178.7
O4—Cu1—O2	101.08 (8)	O4—C9—C8	128.7 (3)
O4—Cu1—O5	84.55 (7)	O4—C9—C10	112.6 (2)
O4—Cu1—O5ⁱ	161.06 (8)	C8—C9—C10	118.7 (2)
O5ⁱ—Cu1—O2	97.37 (8)	C8—C9—Cu1	94.28 (17)
O5ⁱ—Cu1—O5	76.90 (7)	C10—C9—Cu1	146.95 (18)
C2—O1—Cu1	125.00 (16)	F10—C10—F11	107.2 (2)
C4—O2—Cu1	120.66 (17)	F10—C10—F12	107.2 (2)
C7—O3—Cu1	124.47 (18)	F11—C10—F12	107.7 (2)
C9—O4—Cu1	124.12 (18)	F10—C10—C9	110.8 (2)
N1—O5—Cu1ⁱ	123.68 (14)	F11—C10—C9	110.5 (2)
N1—O5—Cu1	120.78 (14)	F12—C10—C9	113.3 (2)
Cu1ⁱ—O5—Cu1	103.10 (7)	N1—C11—C12	119.8 (2)
C11—N1—O5	120.6 (2)	N1—C11—H11	120.1
C11—N1—C15	121.3 (2)	C12—C11—H11	120.1
O5—N1—C15	117.9 (2)	C11—C12—C13	120.9 (2)
C11—N1—Cu1ⁱ	109.45 (16)	C11—C12—H12	119.5
C15—N1—Cu1ⁱ	120.81 (16)	C13—C12—H12	119.5
F3—C1—F1	106.88 (13)	C12—C13—C14	117.0 (2)
F3—C1—F2	106.82 (13)	C12—C13—C16	121.4 (2)
F1—C1—F2	106.45 (13)	C14—C13—C16	121.6 (2)
F3—C1—C2	109.60 (18)	C15—C14—C13	120.6 (2)
F1—C1—C2	113.95 (18)	C15—C14—H14	119.7
F2—C1—C2	112.73 (19)	C13—C14—H14	119.7
O1—C2—C3	130.7 (2)	N1—C15—C14	120.2 (2)
O1—C2—C1	113.9 (2)	N1—C15—H15	119.9
C3—C2—C1	115.4 (2)	C14—C15—H15	119.9
C3—C2—Cu1	97.93 (16)	C21—C16—C17	119.1 (2)
C1—C2—Cu1	145.40 (16)	C21—C16—C13	120.6 (2)
C2—C3—C4	122.9 (2)	C17—C16—C13	120.3 (2)
C2—C3—H3	118.5	C18—C17—C16	120.3 (3)
C4—C3—H3	118.5	C18—C17—H17	119.9
O2—C4—C3	128.2 (2)	C16—C17—H17	119.9
O2—C4—C5	116.2 (2)	C19—C18—C17	120.6 (3)
C3—C4—C5	115.6 (2)	C19—C18—H18	119.7
C3—C4—Cu1	89.46 (16)	C17—C18—H18	119.7
C5—C4—Cu1	154.41 (17)	C20—C19—C18	119.7 (3)
F6'—C5—F4	135.8 (5)	C20—C19—H19	120.1
F4—C5—F6	106.84 (14)	C18—C19—H19	120.1
F6'—C5—F5'	106.86 (14)	C19—C20—C21	120.3 (3)
F4—C5—F5'	64.2 (3)	C19—C20—H20	119.9
F6—C5—F5'	127.3 (4)	C21—C20—H20	119.9
F6'—C5—F4'	106.77 (15)	C16—C21—C20	120.1 (3)
F4—C5—F4'	46.5 (3)	C16—C21—H21	119.9
F6—C5—F4'	66.4 (4)	C20—C21—H21	119.9
F5'—C5—F4'	106.66 (14)	F4'—F4—C5	66.82 (18)
F6'—C5—F5	69.7 (4)	F4'—F4—F5'	119.4 (3)
F4—C5—F5	106.75 (14)	C5—F4—F5'	57.93 (16)
F6—C5—F5	106.59 (14)	F5'—F5—C5	68.07 (17)
F4'—C5—F5	139.5 (4)	F5'—F5—F6'	114.9 (4)
F6'—C5—C4	109.4 (4)	C5—F5—F6'	55.1 (2)
F4—C5—C4	112.7 (3)	F6'—F6—C5	69.2 (2)
F6—C5—C4	113.5 (3)	F6'—F6—F4'	124.3 (2)
F5'—C5—C4	117.6 (3)	C5—F6—F4'	56.8 (2)
F4'—C5—C4	109.0 (3)	F4—F4'—C5	66.69 (17)
F5—C5—C4	110.1 (3)	F4—F4'—F6	115.9 (4)
F7—C6—F8	107.26 (13)	C5—F4'—F6	56.8 (2)
F7—C6—F9	106.60 (13)	F5—F5'—C5	68.22 (18)
F8—C6—F9	106.74 (13)	F5—F5'—F4	124.5 (2)
F7—C6—C7	112.20 (19)	C5—F5'—F4	57.91 (16)
F8—C6—C7	111.06 (18)	F6—F6'—C5	69.3 (2)
F9—C6—C7	112.64 (19)	F6—F6'—F5	118.1 (4)
O3—C7—C8	128.7 (2)	C5—F6'—F5	55.2 (2)

O4—Cu1—O1—C2	−124.4 (2)	O4—Cu1—C8—C9	−1.75 (16)
O5ⁱ—Cu1—O1—C2	74.2 (2)	O1—Cu1—C8—C9	−7.0 (2)
O2—Cu1—O1—C2	−23.3 (2)	O5ⁱ—Cu1—C8—C9	151.74 (16)
O5—Cu1—O1—C2	151.0 (2)	O2—Cu1—C8—C9	−100.53 (17)
O3—Cu1—O2—C4	−158.9 (2)	O5—Cu1—C8—C9	82.53 (17)
O4—Cu1—O2—C4	108.8 (2)	Cu1—O4—C9—C8	−4.4 (4)
O1—Cu1—O2—C4	19.5 (2)	Cu1—O4—C9—C10	176.38 (17)
O5ⁱ—Cu1—O2—C4	−66.9 (2)	C7—C8—C9—O4	1.0 (5)
O4—Cu1—O3—C7	1.8 (2)	Cu1—C8—C9—O4	2.5 (2)
O5ⁱ—Cu1—O3—C7	163.5 (2)	C7—C8—C9—C10	−179.8 (3)
O2—Cu1—O3—C7	−99.2 (2)	Cu1—C8—C9—C10	−178.3 (3)
O5—Cu1—O3—C7	86.5 (2)	C7—C8—C9—Cu1	−1.5 (3)
O3—Cu1—O4—C9	2.8 (2)	O3—Cu1—C9—O4	−177.1 (2)
O1—Cu1—O4—C9	178.4 (2)	O1—Cu1—C9—O4	−1.7 (2)
O5ⁱ—Cu1—O4—C9	−102.3 (3)	O5ⁱ—Cu1—C9—O4	131.5 (2)
O2—Cu1—O4—C9	91.0 (2)	O2—Cu1—C9—O4	−93.2 (2)
O5—Cu1—O4—C9	−90.5 (2)	O5—Cu1—C9—O4	87.5 (2)
O3—Cu1—O5—N1	−125.16 (16)	O3—Cu1—C9—C8	−0.53 (17)
O4—Cu1—O5—N1	−32.87 (16)	O4—Cu1—C9—C8	176.5 (3)
O1—Cu1—O5—N1	56.90 (16)	O1—Cu1—C9—C8	174.81 (16)
O5ⁱ—Cu1—O5—N1	143.3 (2)	O5ⁱ—Cu1—C9—C8	−52.0 (3)
O3—Cu1—O5—Cu1ⁱ	91.59 (9)	O2—Cu1—C9—C8	83.36 (18)
O4—Cu1—O5—Cu1ⁱ	−176.12 (9)	O5—Cu1—C9—C8	−95.98 (17)
O1—Cu1—O5—Cu1ⁱ	−86.35 (8)	O3—Cu1—C9—C10	176.8 (3)
O5ⁱ—Cu1—O5—Cu1ⁱ	0.0	O4—Cu1—C9—C10	−6.1 (3)
Cu1ⁱ—O5—N1—C11	79.3 (3)	O1—Cu1—C9—C10	−7.9 (3)
Cu1—O5—N1—C11	−56.3 (3)	O5ⁱ—Cu1—C9—C10	125.3 (3)
Cu1ⁱ—O5—N1—C15	−104.5 (2)	O2—Cu1—C9—C10	−99.3 (3)
Cu1—O5—N1—C15	119.9 (2)	O5—Cu1—C9—C10	81.4 (3)
Cu1—O5—N1—Cu1ⁱ	−135.6 (2)	O4—C9—C10—F10	59.0 (3)
Cu1—O1—C2—C3	18.9 (4)	C8—C9—C10—F10	−120.3 (3)
Cu1—O1—C2—C1	−162.19 (14)	Cu1—C9—C10—F10	62.7 (4)
F3—C1—C2—O1	116.4 (2)	O4—C9—C10—F11	−59.7 (3)
F1—C1—C2—O1	−3.3 (3)	C8—C9—C10—F11	121.0 (3)
F2—C1—C2—O1	−124.8 (2)	Cu1—C9—C10—F11	−55.9 (4)
F3—C1—C2—C3	−64.5 (3)	O4—C9—C10—F12	179.4 (2)
F1—C1—C2—C3	175.8 (2)	C8—C9—C10—F12	0.1 (4)
F2—C1—C2—C3	54.3 (3)	Cu1—C9—C10—F12	−176.8 (2)
F3—C1—C2—Cu1	98.8 (3)	O5—N1—C11—C12	175.6 (2)
F1—C1—C2—Cu1	−20.9 (3)	C15—N1—C11—C12	−0.5 (4)
F2—C1—C2—Cu1	−142.3 (3)	Cu1ⁱ—N1—C11—C12	−148.8 (2)
O3—Cu1—C2—O1	179.0 (2)	N1—C11—C12—C13	−0.8 (4)
O4—Cu1—C2—O1	57.4 (2)	C11—C12—C13—C14	1.9 (4)
O5ⁱ—Cu1—C2—O1	−103.6 (2)	C11—C12—C13—C16	−177.1 (2)
O2—Cu1—C2—O1	154.8 (2)	C12—C13—C14—C15	−1.7 (4)
O5—Cu1—C2—O1	−30.8 (2)	C16—C13—C14—C15	177.3 (2)
O3—Cu1—C2—C3	13.4 (3)	C11—N1—C15—C14	0.7 (4)
O4—Cu1—C2—C3	−108.30 (17)	O5—N1—C15—C14	−175.5 (2)
O1—Cu1—C2—C3	−165.7 (3)	Cu1ⁱ—N1—C15—C14	145.5 (2)
O5ⁱ—Cu1—C2—C3	90.73 (17)	C13—C14—C15—N1	0.5 (4)
O2—Cu1—C2—C3	−10.82 (16)	C12—C13—C16—C21	142.6 (3)
O5—Cu1—C2—C3	163.51 (16)	C14—C13—C16—C21	−36.3 (4)
O3—Cu1—C2—C1	−151.5 (2)	C12—C13—C16—C17	−37.6 (4)
O4—Cu1—C2—C1	86.9 (3)	C14—C13—C16—C17	143.5 (3)
O1—Cu1—C2—C1	29.5 (2)	C21—C16—C17—C18	−0.2 (4)
O5ⁱ—Cu1—C2—C1	−74.1 (3)	C13—C16—C17—C18	179.9 (3)
O2—Cu1—C2—C1	−175.7 (3)	C16—C17—C18—C19	0.1 (5)
O5—Cu1—C2—C1	−1.3 (3)	C17—C18—C19—C20	0.0 (5)
O1—C2—C3—C4	1.0 (5)	C18—C19—C20—C21	0.0 (5)
C1—C2—C3—C4	−177.9 (2)	C17—C16—C21—C20	0.3 (4)
Cu1—C2—C3—C4	11.5 (3)	C13—C16—C21—C20	−179.9 (3)
Cu1—O2—C4—C3	−9.7 (4)	C19—C20—C21—C16	−0.2 (5)
Cu1—O2—C4—C5	171.25 (17)	F6'—C5—F4—F4'	66.1 (6)
C2—C3—C4—O2	−4.6 (5)	F6—C5—F4—F4'	30.2 (6)
C2—C3—C4—C5	174.4 (2)	F5'—C5—F4—F4'	154.1 (6)
C2—C3—C4—Cu1	−10.7 (3)	F5—C5—F4—F4'	144.0 (6)
O3—Cu1—C4—O2	22.0 (2)	C4—C5—F4—F4'	−95.1 (6)
O4—Cu1—C4—O2	−76.0 (2)	F6'—C5—F4—F5'	−88.0 (4)
O1—Cu1—C4—O2	−159.0 (2)	F6—C5—F4—F5'	−123.8 (5)
O5ⁱ—Cu1—C4—O2	114.2 (2)	F4'—C5—F4—F5'	−154.1 (6)
O5—Cu1—C4—O2	168.04 (19)	F5—C5—F4—F5'	−10.1 (5)
O3—Cu1—C4—C3	−165.59 (16)	C4—C5—F4—F5'	110.8 (4)
O4—Cu1—C4—C3	96.36 (16)	F6'—C5—F5—F5'	146.6 (6)
O1—Cu1—C4—C3	13.38 (16)	F4—C5—F5—F5'	13.2 (6)
O5ⁱ—Cu1—C4—C3	−73.38 (16)	F6—C5—F5—F5'	127.1 (6)
O2—Cu1—C4—C3	172.4 (3)	F4'—C5—F5—F5'	54.2 (9)
O5—Cu1—C4—C3	−19.6 (3)	C4—C5—F5—F5'	−109.4 (6)
O3—Cu1—C4—C5	3.6 (4)	F4—C5—F5—F6'	−133.4 (5)
O4—Cu1—C4—C5	−94.5 (4)	F6—C5—F5—F6'	−19.4 (5)
O1—Cu1—C4—C5	−177.4 (4)	F5'—C5—F5—F6'	−146.6 (6)
O5ⁱ—Cu1—C4—C5	95.8 (4)	F4'—C5—F5—F6'	−92.3 (5)
O2—Cu1—C4—C5	−18.4 (3)	C4—C5—F5—F6'	104.0 (4)
O5—Cu1—C4—C5	149.6 (3)	F4—C5—F6—F6'	141.9 (6)
O2—C4—C5—F6'	−55.4 (6)	F5'—C5—F6—F6'	71.9 (6)
C3—C4—C5—F6'	125.4 (6)	F4'—C5—F6—F6'	165.4 (7)
Cu1—C4—C5—F6'	−42.6 (7)	F5—C5—F6—F6'	28.1 (6)
O2—C4—C5—F4	110.8 (5)	C4—C5—F6—F6'	−93.2 (7)
C3—C4—C5—F4	−68.4 (5)	F6'—C5—F6—F4'	−165.4 (7)
Cu1—C4—C5—F4	123.6 (5)	F4—C5—F6—F4'	−23.5 (4)
O2—C4—C5—F6	−10.8 (4)	F5'—C5—F6—F4'	−93.5 (4)
C3—C4—C5—F6	170.0 (4)	F5—C5—F6—F4'	−137.3 (4)
Cu1—C4—C5—F6	2.0 (6)	C4—C5—F6—F4'	101.3 (3)
O2—C4—C5—F5'	−177.5 (5)	F5'—F4—F4'—C5	25.2 (5)
C3—C4—C5—F5'	3.3 (5)	C5—F4—F4'—F6	−29.3 (4)
Cu1—C4—C5—F5'	−164.7 (5)	F5'—F4—F4'—F6	−4.1 (8)
O2—C4—C5—F4'	61.0 (5)	F6'—C5—F4'—F4	−138.2 (6)
C3—C4—C5—F4'	−118.2 (5)	F6—C5—F4'—F4	−148.3 (6)
Cu1—C4—C5—F4'	73.8 (6)	F5'—C5—F4'—F4	−24.3 (6)
O2—C4—C5—F5	−130.2 (4)	F5—C5—F4'—F4	−60.1 (8)
C3—C4—C5—F5	50.6 (4)	C4—C5—F4'—F4	103.7 (5)
Cu1—C4—C5—F5	−117.3 (5)	F6'—C5—F4'—F6	10.0 (5)
Cu1—O3—C7—C8	−5.6 (4)	F4—C5—F4'—F6	148.3 (6)
Cu1—O3—C7—C6	174.94 (14)	F5'—C5—F4'—F6	124.0 (5)
F7—C6—C7—O3	2.6 (3)	F5—C5—F4'—F6	88.2 (5)
F8—C6—C7—O3	−117.5 (2)	C4—C5—F4'—F6	−108.1 (3)
F9—C6—C7—O3	122.9 (2)	F6'—F6—F4'—F4	15.9 (10)
F7—C6—C7—C8	−177.0 (2)	C5—F6—F4'—F4	32.5 (5)
F8—C6—C7—C8	63.0 (3)	F6'—F6—F4'—C5	−16.5 (7)
F9—C6—C7—C8	−56.7 (3)	F6'—F5—F5'—C5	29.9 (4)
F7—C6—C7—Cu1	8.2 (4)	C5—F5—F5'—F4	−14.5 (6)
F8—C6—C7—Cu1	−111.8 (3)	F6'—F5—F5'—F4	15.4 (9)
F9—C6—C7—Cu1	128.5 (3)	F6'—C5—F5'—F5	−32.7 (7)
O4—Cu1—C7—O3	−178.1 (2)	F4—C5—F5'—F5	−165.9 (7)
O1—Cu1—C7—O3	166.4 (2)	F6—C5—F5'—F5	−73.9 (5)
O5ⁱ—Cu1—C7—O3	−17.9 (2)	F4'—C5—F5'—F5	−146.6 (6)
O2—Cu1—C7—O3	80.6 (2)	C4—C5—F5'—F5	90.8 (6)
O5—Cu1—C7—O3	−94.6 (2)	F6'—C5—F5'—F4	133.3 (5)
O3—Cu1—C7—C8	175.6 (3)	F6—C5—F5'—F4	92.1 (3)
O4—Cu1—C7—C8	−2.47 (17)	F4'—C5—F5'—F4	19.3 (5)
O1—Cu1—C7—C8	−17.9 (3)	F5—C5—F5'—F4	165.9 (7)
O5ⁱ—Cu1—C7—C8	157.75 (17)	C4—C5—F5'—F4	−103.3 (3)
O2—Cu1—C7—C8	−103.75 (18)	F4'—F4—F5'—F5	−11.6 (11)
O5—Cu1—C7—C8	81.09 (18)	C5—F4—F5'—F5	15.9 (7)
O3—Cu1—C7—C6	−9.1 (3)	F4'—F4—F5'—C5	−27.5 (6)
O4—Cu1—C7—C6	172.8 (3)	F4'—F6—F6'—C5	14.8 (7)
O1—Cu1—C7—C6	157.4 (3)	C5—F6—F6'—F5	−26.6 (5)
O5ⁱ—Cu1—C7—C6	−27.0 (3)	F4'—F6—F6'—F5	−11.8 (10)
O2—Cu1—C7—C6	71.5 (3)	F4—C5—F6'—F6	−57.8 (7)
O5—Cu1—C7—C6	−103.6 (3)	F5'—C5—F6'—F6	−127.8 (6)
O3—C7—C8—C9	4.6 (5)	F4'—C5—F6'—F6	−13.9 (6)
C6—C7—C8—C9	−175.9 (2)	F5—C5—F6'—F6	−151.2 (6)
Cu1—C7—C8—C9	1.5 (3)	C4—C5—F6'—F6	103.9 (6)
O3—C7—C8—Cu1	3.1 (2)	F4—C5—F6'—F5	93.5 (5)
C6—C7—C8—Cu1	−177.4 (2)	F6—C5—F6'—F5	151.2 (6)
O3—Cu1—C8—C7	−2.18 (16)	F5'—C5—F6'—F5	23.4 (4)
O4—Cu1—C8—C7	176.8 (2)	F4'—C5—F6'—F5	137.3 (4)
O1—Cu1—C8—C7	171.52 (16)	C4—C5—F6'—F5	−104.9 (3)
O5ⁱ—Cu1—C8—C7	−29.7 (2)	F5'—F5—F6'—F6	−3.6 (8)
O2—Cu1—C8—C7	77.99 (18)	C5—F5—F6'—F6	30.7 (6)
O5—Cu1—C8—C7	−98.95 (18)	F5'—F5—F6'—C5	−34.3 (5)
O3—Cu1—C8—C9	179.3 (2)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₅HF₆O₂)₄(C₁₁H₉NO)₂]
M_r	1297.70
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	10.3830 (4), 10.7870 (4), 11.2498 (4)
α, β, γ (°)	99.055 (2), 99.036 (2), 98.258 (2)
V (Å³)	1210.40 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.18 × 0.10 × 0.09

Data collection
Diffractometer	Bruker X8 Kappa CCD APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.836, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	47759, 6427, 5461
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.04
No. of reflections	6427
No. of parameters	397
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.21, −1.40

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 2005), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Acknowledgements

We are grateful to the Fundação para a Ciência e a Tecnologia (FCT, Portugal) for their general financial support, for specific funding toward the purchase of the single-crystal X-ray diffractometer, and for the post-doctoral and PhD research grants Nos. SFRH/BPD/63736/2009 (to JAF) and SFRH/BD/46601/2008 (to PS), respectively. We further acknowledge the FCT for additional funding under the R&D project PTDC/QUI/69302/2006.

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