(N,N-Diethyl­nicotinamide-κN1)bis­[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato-κ2O,O′]copper(II)

Maharramov, A.M.; Mardanova, V.I.; Chyraqov, F.; Gurbanov, A.V.; Ng, S.W.

doi:10.1107/S1600536811014401

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m708-m709

doi:10.1107/S1600536811014401

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(N,N-Diethylnicotinamide-κN¹)bis[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato-κ²O,O′]copper(II)

Abel M. Maharramov,^a Vusala I. Mardanova,^a Famil Chyraqov,^a Atash V. Gurbanov ^a and Seik Weng Ng ^b ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 April 2011; accepted 17 April 2011; online 7 May 2011)

In the title compound, [Cu(C₈H₄F₃O₂S)₂(C₁₀H₁₄N₂O)], the Cu^II atom exists in a distorted CuNO₄ square-pyramidal geometry; the metal atom lies above a square plane defined by four O atoms of the two chelating anionic ligands, displaced in the direction of the axial occupant, the pyridine N atom, by 0.179 (1) Å. Weak intermolecular C—H⋯O and C—H⋯F hydrogen bonding is present in the crystal structure. One thienyl ring is disordered over two orientations in an occupancy ratio of 0.69 (1):0.31.

Related literature

For the related crystal structure of bis[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato]copper(II), see: Lecomte et al. (1988 ); Wang et al. (1996 ); Xu et al. (2010 ). For some adducts with N-heterocycles, see: Gou et al. (1991 ); Li et al. (1994 ); Liu et al. (1986 ); Yu et al. (1988 ).

Experimental

Crystal data

[Cu(C₈H₄F₃O₂S)₂(C₁₀H₁₄N₂O)]
M_r = 684.12
Triclinic, $[P \overline 1]$
a = 11.4324 (5) Å
b = 12.8606 (5) Å
c = 13.0104 (5) Å
α = 62.837 (1)°
β = 64.110 (1)°
γ = 88.783 (1)°
V = 1492.72 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.618, T_max = 0.746
16434 measured reflections
6849 independent reflections
5423 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.152
S = 1.05
6849 reflections
392 parameters
80 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9432 (19)
Cu1—O2	1.942 (2)
Cu1—O3	1.944 (2)
Cu1—O4	1.934 (2)
Cu1—N1	2.262 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O5ⁱ	0.93	2.49	3.358 (7)	156
C19—H19⋯O5ⁱⁱ	0.93	2.56	3.338 (6)	141
C24—H24C⋯F1ⁱⁱⁱ	0.96	2.36	3.233 (13)	151
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014401/xu5194sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014401/xu5194Isup2.hkl

checkCIF report

Comment top

Square-planar bis[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato]copper is a Lewis acid that forms adducts with a number of N-heterocycles. The parent Lewis acid exists as a square-planar molecule; its crystal structure has been determined several times (Lecomte et al., 1988; Wang et al., 1996; Xu et al., 2010). For most adducts, the Cu atom exists in a six-coordinate geometry, e.g., the pyridine adduct (Liu et al., 1986). The 4,4'-bipyridine adduct exists in two forms; in one form, the Cu atom is octahedrally coordinated (Gou et al., 1991). The other is a dinuclear adduct in which the Cu atom shows the square-pyramidal coordination. In the title N,N-diethylbenzamide adduct (Scheme I), the Cu atom is similarly five-coordinate. The metal atom lies above the square plane defined by the O atoms of the two chelating anionic ligands in the direction of the axial occupant by 0.179 (1) Å.

Related literature top

For the related crystal structure of bis[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato]copper, see: Lecomte et al. (1988); Wang et al. (1996); Xu et al. (2010). For some adducts with N-heterocycles, see: Gou et al. (1991); Li et al. (1994); Liu et al. (1986); Yu et al. (1988).

Experimental top

Bis[4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dionato]copper was synthesized by using a literature procedure (Lecomte et al., 1988; Wang et al., 1996; Xu et al., 2010). A solution of theonyltrifluoroacetylacetone (0.44 g, 0.002 mol) in ethanol (50 ml) and N,N-diethylnicotinamide (0.18 g, 0.001 mol) was added to a solution of copper sulfate pentahydrate (0.25 g, 0.001 mol) dissolved in water (50 ml). The resulting green solution has heated for a hour and then set aside for a week. The solid was filtered and recrystallized from ethanol (80%, m.p. 515 K); yield 65%. CHN&S elemental analysis. Found: C 45.69, H 3.31, S 9.48, F 16.75%; calculated for C₂₆H₂₂N₂O₅CuF₆S₂: C 45.61, H 3.22, S 9.36, F 16.67%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cu(C₁₀H₁₄N₂O)(C₈H₄F₃O₂S)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

(N,N-Diethylnicotinamide-κN¹)bis[4,4,4-trifluoro-1- (thien-2-yl)butane-1,3-dionato-κ²O,O']copper(II) top

Crystal data top

[Cu(C₈H₄F₃O₂S)₂(C₁₀H₁₄N₂O)]	Z = 2
M_r = 684.12	F(000) = 694
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4324 (5) Å	Cell parameters from 5935 reflections
b = 12.8606 (5) Å	θ = 2.4–27.9°
c = 13.0104 (5) Å	µ = 0.95 mm⁻¹
α = 62.837 (1)°	T = 293 K
β = 64.110 (1)°	Prism, green
γ = 88.783 (1)°	0.30 × 0.30 × 0.30 mm
V = 1492.72 (10) Å³

Data collection top

Bruker APEXII diffractometer	6849 independent reflections
Radiation source: fine-focus sealed tube	5423 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.618, T_max = 0.746	k = −16→16
16434 measured reflections	l = −16→16

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) = 0.152	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0881P)² + 0.5656P] where P = (F_o² + 2F_c²)/3
6849 reflections	(Δ/σ)_max = 0.001
392 parameters	Δρ_max = 0.80 e Å⁻³
80 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu(C₈H₄F₃O₂S)₂(C₁₀H₁₄N₂O)]	γ = 88.783 (1)°
M_r = 684.12	V = 1492.72 (10) Å³
Triclinic, P1	Z = 2
a = 11.4324 (5) Å	Mo Kα radiation
b = 12.8606 (5) Å	µ = 0.95 mm⁻¹
c = 13.0104 (5) Å	T = 293 K
α = 62.837 (1)°	0.30 × 0.30 × 0.30 mm
β = 64.110 (1)°

Data collection top

Bruker APEXII diffractometer	6849 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5423 reflections with I > 2σ(I)
T_min = 0.618, T_max = 0.746	R_int = 0.021
16434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	80 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.05	Δρ_max = 0.80 e Å⁻³
6849 reflections	Δρ_min = −0.48 e Å⁻³
392 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.30419 (3)	0.56562 (3)	0.41193 (3)	0.04574 (14)
S1	0.54183 (10)	0.72016 (9)	0.54939 (11)	0.0756 (3)
S2	0.6254 (2)	0.8905 (2)	−0.13505 (17)	0.1145 (10)	0.690 (4)
S2'	0.6483 (8)	0.9072 (7)	0.0696 (9)	0.1087 (19)	0.310 (4)
F1	0.0837 (4)	0.2134 (3)	0.8976 (3)	0.1525 (16)
F2	0.1339 (5)	0.1709 (2)	0.7503 (4)	0.176 (2)
F3	−0.0184 (3)	0.2524 (3)	0.7936 (4)	0.1409 (14)
F4	0.2363 (3)	0.4454 (3)	0.1471 (4)	0.1172 (10)
F5	0.0665 (2)	0.5072 (3)	0.2318 (2)	0.0937 (8)
F6	0.2142 (3)	0.6186 (3)	0.0325 (2)	0.1167 (11)
O1	0.39754 (19)	0.59008 (18)	0.4959 (2)	0.0488 (4)
O2	0.1956 (2)	0.41288 (18)	0.5671 (2)	0.0517 (5)
O3	0.4426 (2)	0.69749 (19)	0.2487 (2)	0.0571 (5)
O4	0.2310 (2)	0.5291 (2)	0.3203 (2)	0.0563 (5)
O5	0.2239 (4)	1.0114 (2)	0.4841 (4)	0.0956 (10)
N1	0.1673 (2)	0.6845 (2)	0.4613 (2)	0.0492 (5)
N2	0.1538 (5)	0.8623 (4)	0.6909 (4)	0.1059 (14)
C1	0.5746 (4)	0.7210 (4)	0.6636 (5)	0.0816 (12)
H1	0.6319	0.7840	0.6463	0.098*
C2	0.5103 (4)	0.6226 (4)	0.7807 (5)	0.0777 (11)
H2	0.5200	0.6105	0.8524	0.093*
C3	0.4245 (3)	0.5360 (3)	0.7883 (4)	0.0575 (8)
H3	0.3709	0.4635	0.8628	0.069*
C4	0.4369 (3)	0.5821 (3)	0.6599 (3)	0.0504 (6)
C5	0.3676 (3)	0.5306 (3)	0.6161 (3)	0.0451 (6)
C6	0.2716 (3)	0.4211 (3)	0.7077 (3)	0.0548 (7)
H6	0.2583	0.3806	0.7935	0.066*
C7	0.1978 (3)	0.3724 (3)	0.6751 (3)	0.0490 (6)
C8	0.1005 (4)	0.2514 (3)	0.7805 (3)	0.0661 (9)
C9	0.7529 (7)	0.9912 (6)	−0.1766 (11)	0.122 (3)	0.690 (4)
H9	0.8160	1.0435	−0.2634	0.147*	0.690 (4)
C10	0.7554 (10)	0.9894 (8)	−0.0739 (10)	0.122 (3)	0.690 (4)
H10	0.8190	1.0391	−0.0801	0.146*	0.690 (4)
C11	0.6508 (12)	0.9040 (9)	0.0415 (15)	0.1087 (19)	0.690 (4)
H11	0.6366	0.8905	0.1230	0.130*	0.690 (4)
C9'	0.734 (2)	1.0246 (18)	−0.0845 (17)	0.122 (3)	0.31
H9'	0.7950	1.0882	−0.1074	0.146*	0.310 (4)
C10'	0.7052 (18)	1.0171 (19)	−0.170 (3)	0.122 (3)	0.31
H10'	0.7414	1.0720	−0.2599	0.147*	0.310 (4)
C11'	0.6135 (16)	0.9143 (16)	−0.1017 (10)	0.1145 (10)	0.31
H11'	0.5798	0.8933	−0.1447	0.137*	0.310 (4)
C12	0.5686 (4)	0.8400 (3)	0.0299 (4)	0.0743 (10)
C13	0.4566 (3)	0.7379 (3)	0.1354 (3)	0.0562 (7)
C14	0.3739 (4)	0.6899 (3)	0.1052 (3)	0.0648 (9)
H14	0.3900	0.7269	0.0185	0.078*
C15	0.2713 (3)	0.5912 (3)	0.1982 (3)	0.0556 (7)
C16	0.1958 (4)	0.5407 (4)	0.1521 (3)	0.0730 (10)
C17	0.0474 (3)	0.6793 (3)	0.4681 (3)	0.0534 (7)
H17	0.0212	0.6284	0.4456	0.064*
C18	−0.0389 (3)	0.7461 (3)	0.5069 (4)	0.0635 (8)
H18	−0.1210	0.7415	0.5089	0.076*
C19	−0.0020 (3)	0.8193 (3)	0.5426 (3)	0.0612 (8)
H19	−0.0591	0.8649	0.5697	0.073*
C20	0.1210 (3)	0.8250 (3)	0.5380 (3)	0.0523 (7)
C21	0.2024 (3)	0.7576 (3)	0.4951 (3)	0.0523 (7)
H21	0.2863	0.7629	0.4894	0.063*
C22	0.1703 (4)	0.9079 (3)	0.5698 (4)	0.0650 (9)
C23	0.0985 (10)	0.7336 (7)	0.7935 (6)	0.176 (4)
H23A	0.1451	0.7088	0.8449	0.211*
H23B	0.1097	0.6845	0.7526	0.211*
C24	−0.0489 (10)	0.7181 (11)	0.8820 (10)	0.280 (9)
H24A	−0.0870	0.6352	0.9483	0.419*
H24B	−0.0939	0.7437	0.8301	0.419*
H24C	−0.0589	0.7656	0.9235	0.419*
C25	0.1991 (7)	0.9431 (6)	0.7257 (7)	0.129 (2)
H25A	0.1360	0.9222	0.8154	0.154*
H25B	0.2010	1.0251	0.6680	0.154*
C26	0.3380 (8)	0.9343 (6)	0.7135 (8)	0.159 (3)
H26A	0.3657	0.9904	0.7325	0.238*
H26B	0.4002	0.9527	0.6255	0.238*
H26C	0.3351	0.8545	0.7748	0.238*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0466 (2)	0.0444 (2)	0.0387 (2)	−0.00173 (14)	−0.01578 (15)	−0.01905 (15)
S1	0.0621 (5)	0.0736 (6)	0.0836 (7)	−0.0044 (4)	−0.0266 (5)	−0.0406 (5)
S2	0.1000 (14)	0.1279 (17)	0.0473 (9)	−0.0235 (11)	−0.0234 (9)	−0.0022 (9)
S2'	0.097 (2)	0.0894 (19)	0.091 (4)	−0.0344 (15)	−0.034 (2)	−0.0166 (19)
F1	0.195 (3)	0.123 (2)	0.0635 (16)	−0.084 (2)	−0.056 (2)	0.0088 (16)
F2	0.219 (4)	0.0509 (15)	0.139 (3)	−0.0227 (19)	0.008 (3)	−0.0456 (17)
F3	0.0871 (19)	0.100 (2)	0.145 (3)	−0.0385 (16)	−0.046 (2)	−0.0009 (19)
F4	0.131 (2)	0.138 (2)	0.165 (3)	0.042 (2)	−0.093 (2)	−0.116 (2)
F5	0.0675 (14)	0.127 (2)	0.0798 (15)	−0.0058 (13)	−0.0363 (12)	−0.0444 (15)
F6	0.117 (2)	0.148 (3)	0.0627 (14)	−0.0227 (18)	−0.0517 (15)	−0.0253 (15)
O1	0.0455 (10)	0.0478 (10)	0.0471 (11)	0.0010 (8)	−0.0206 (9)	−0.0203 (9)
O2	0.0570 (12)	0.0456 (10)	0.0452 (11)	−0.0042 (9)	−0.0225 (9)	−0.0186 (9)
O3	0.0571 (12)	0.0524 (11)	0.0442 (11)	−0.0072 (9)	−0.0162 (10)	−0.0178 (9)
O4	0.0608 (12)	0.0578 (12)	0.0423 (11)	−0.0058 (10)	−0.0194 (10)	−0.0234 (10)
O5	0.123 (3)	0.0534 (15)	0.117 (3)	0.0057 (16)	−0.073 (2)	−0.0324 (16)
N1	0.0512 (13)	0.0482 (13)	0.0499 (13)	0.0069 (10)	−0.0247 (11)	−0.0251 (11)
N2	0.172 (4)	0.076 (2)	0.086 (3)	0.004 (2)	−0.062 (3)	−0.051 (2)
C1	0.061 (2)	0.093 (3)	0.120 (4)	0.013 (2)	−0.044 (2)	−0.074 (3)
C2	0.077 (3)	0.098 (3)	0.094 (3)	0.021 (2)	−0.054 (2)	−0.063 (3)
C3	0.0663 (19)	0.0606 (18)	0.071 (2)	0.0141 (15)	−0.0448 (17)	−0.0397 (16)
C4	0.0415 (14)	0.0540 (16)	0.0604 (17)	0.0091 (12)	−0.0245 (13)	−0.0317 (14)
C5	0.0410 (14)	0.0476 (14)	0.0485 (15)	0.0098 (11)	−0.0203 (12)	−0.0262 (12)
C6	0.0559 (17)	0.0551 (17)	0.0452 (15)	−0.0030 (13)	−0.0221 (14)	−0.0203 (13)
C7	0.0496 (15)	0.0436 (14)	0.0449 (15)	0.0010 (12)	−0.0174 (13)	−0.0200 (12)
C8	0.075 (2)	0.0557 (18)	0.0492 (17)	−0.0144 (16)	−0.0257 (16)	−0.0150 (15)
C9	0.078 (6)	0.105 (5)	0.082 (4)	−0.013 (4)	−0.024 (5)	0.017 (4)
C10	0.090 (4)	0.079 (6)	0.121 (5)	−0.026 (4)	−0.046 (4)	0.004 (4)
C11	0.097 (2)	0.0894 (19)	0.091 (4)	−0.0344 (15)	−0.034 (2)	−0.0166 (19)
C9'	0.090 (4)	0.079 (6)	0.121 (5)	−0.026 (4)	−0.046 (4)	0.004 (4)
C10'	0.078 (6)	0.105 (5)	0.082 (4)	−0.013 (4)	−0.024 (5)	0.017 (4)
C11'	0.1000 (14)	0.1279 (17)	0.0473 (9)	−0.0235 (11)	−0.0234 (9)	−0.0022 (9)
C12	0.067 (2)	0.064 (2)	0.0507 (19)	−0.0076 (17)	−0.0194 (17)	−0.0047 (16)
C13	0.0550 (17)	0.0488 (16)	0.0433 (15)	0.0010 (13)	−0.0152 (13)	−0.0144 (13)
C14	0.069 (2)	0.064 (2)	0.0433 (16)	−0.0022 (16)	−0.0234 (15)	−0.0156 (15)
C15	0.0583 (18)	0.0597 (18)	0.0472 (16)	0.0064 (14)	−0.0244 (14)	−0.0260 (14)
C16	0.074 (2)	0.088 (3)	0.057 (2)	0.002 (2)	−0.0340 (19)	−0.0326 (19)
C17	0.0526 (16)	0.0541 (16)	0.0524 (16)	0.0036 (13)	−0.0256 (14)	−0.0249 (14)
C18	0.0512 (18)	0.068 (2)	0.069 (2)	0.0117 (15)	−0.0291 (16)	−0.0324 (18)
C19	0.0613 (19)	0.0570 (18)	0.0599 (19)	0.0201 (15)	−0.0257 (16)	−0.0287 (16)
C20	0.0638 (18)	0.0424 (14)	0.0487 (16)	0.0109 (13)	−0.0266 (14)	−0.0214 (13)
C21	0.0568 (17)	0.0479 (15)	0.0616 (18)	0.0118 (13)	−0.0347 (15)	−0.0284 (14)
C22	0.081 (2)	0.0492 (18)	0.083 (2)	0.0232 (17)	−0.047 (2)	−0.0395 (18)
C23	0.298 (12)	0.133 (5)	0.088 (4)	−0.042 (6)	−0.093 (6)	−0.045 (4)
C24	0.330 (17)	0.313 (16)	0.147 (8)	−0.124 (13)	−0.039 (9)	−0.141 (10)
C25	0.192 (7)	0.111 (4)	0.128 (5)	0.015 (4)	−0.081 (5)	−0.089 (4)
C26	0.222 (9)	0.123 (5)	0.202 (8)	0.032 (6)	−0.136 (8)	−0.099 (6)

Geometric parameters (Å, º) top

Cu1—O1	1.9432 (19)	C9—C10	1.339 (8)
Cu1—O2	1.942 (2)	C9—H9	0.9300
Cu1—O3	1.944 (2)	C10—C11	1.369 (10)
Cu1—O4	1.934 (2)	C10—H10	0.9300
Cu1—N1	2.262 (2)	C11—C12	1.361 (10)
S1—C1	1.688 (4)	C11—H11	0.9300
S1—C4	1.707 (3)	C9'—C10'	1.338 (11)
S2—C9	1.687 (8)	C9'—H9'	0.9300
S2—C12	1.725 (4)	C10'—C11'	1.344 (11)
S2'—C12	1.641 (9)	C10'—H10'	0.9300
S2'—C9'	1.686 (10)	C11'—C12	1.367 (10)
F1—C8	1.290 (4)	C11'—H11'	0.9300
F2—C8	1.264 (4)	C12—C13	1.463 (4)
F3—C8	1.295 (4)	C13—C14	1.414 (5)
F4—C16	1.321 (4)	C14—C15	1.369 (5)
F5—C16	1.315 (4)	C14—H14	0.9300
F6—C16	1.331 (4)	C15—C16	1.535 (5)
O1—C5	1.265 (3)	C17—C18	1.376 (5)
O2—C7	1.268 (3)	C17—H17	0.9300
O3—C13	1.252 (4)	C18—C19	1.365 (5)
O4—C15	1.262 (4)	C18—H18	0.9300
O5—C22	1.214 (5)	C19—C20	1.383 (5)
N1—C17	1.335 (4)	C19—H19	0.9300
N1—C21	1.337 (4)	C20—C21	1.373 (4)
N2—C22	1.329 (5)	C20—C22	1.502 (4)
N2—C23	1.487 (8)	C21—H21	0.9300
N2—C25	1.487 (5)	C23—C24	1.522 (5)
C1—C2	1.328 (6)	C23—H23A	0.9700
C1—H1	0.9300	C23—H23B	0.9700
C2—C3	1.440 (5)	C24—H24A	0.9600
C2—H2	0.9300	C24—H24B	0.9600
C3—C4	1.433 (5)	C24—H24C	0.9600
C3—H3	0.9300	C25—C26	1.532 (5)
C4—C5	1.467 (4)	C25—H25A	0.9700
C5—C6	1.414 (4)	C25—H25B	0.9700
C6—C7	1.365 (4)	C26—H26A	0.9600
C6—H6	0.9300	C26—H26B	0.9600
C7—C8	1.527 (4)	C26—H26C	0.9600

O4—Cu1—O1	171.65 (9)	C10'—C11'—H11'	119.2
O4—Cu1—O2	87.74 (9)	C12—C11'—H11'	119.2
O1—Cu1—O2	92.01 (8)	C11—C12—C13	127.8 (7)
O4—Cu1—O3	92.32 (9)	C11'—C12—C13	134.9 (10)
O1—Cu1—O3	86.06 (9)	C11'—C12—S2'	105.0 (10)
O2—Cu1—O3	167.13 (10)	C13—C12—S2'	118.7 (4)
O4—Cu1—N1	97.55 (9)	C11—C12—S2	108.8 (7)
O1—Cu1—N1	90.74 (8)	C13—C12—S2	123.2 (3)
O2—Cu1—N1	98.28 (9)	S2'—C12—S2	118.1 (4)
O3—Cu1—N1	94.47 (9)	O3—C13—C14	124.4 (3)
C1—S1—C4	91.7 (2)	O3—C13—C12	115.9 (3)
C9—S2—C12	90.7 (4)	C14—C13—C12	119.8 (3)
C12—S2'—C9'	94.1 (12)	C15—C14—C13	122.7 (3)
C5—O1—Cu1	127.36 (18)	C15—C14—H14	118.6
C7—O2—Cu1	123.57 (18)	C13—C14—H14	118.6
C13—O3—Cu1	127.3 (2)	O4—C15—C14	129.2 (3)
C15—O4—Cu1	123.9 (2)	O4—C15—C16	112.7 (3)
C17—N1—C21	117.6 (3)	C14—C15—C16	118.1 (3)
C17—N1—Cu1	123.2 (2)	F5—C16—F4	106.9 (3)
C21—N1—Cu1	119.0 (2)	F5—C16—F6	106.9 (3)
C22—N2—C23	124.4 (4)	F4—C16—F6	106.7 (3)
C22—N2—C25	118.5 (4)	F5—C16—C15	112.5 (3)
C23—N2—C25	117.1 (4)	F4—C16—C15	110.5 (3)
C2—C1—S1	113.3 (3)	F6—C16—C15	113.1 (3)
C2—C1—H1	123.4	N1—C17—C18	122.8 (3)
S1—C1—H1	123.4	N1—C17—H17	118.6
C1—C2—C3	115.0 (4)	C18—C17—H17	118.6
C1—C2—H2	122.5	C19—C18—C17	118.9 (3)
C3—C2—H2	122.5	C19—C18—H18	120.6
C4—C3—C2	107.4 (3)	C17—C18—H18	120.6
C4—C3—H3	126.3	C18—C19—C20	119.4 (3)
C2—C3—H3	126.3	C18—C19—H19	120.3
C3—C4—C5	129.2 (3)	C20—C19—H19	120.3
C3—C4—S1	112.5 (2)	C21—C20—C19	118.1 (3)
C5—C4—S1	118.2 (2)	C21—C20—C22	119.8 (3)
O1—C5—C6	123.8 (3)	C19—C20—C22	122.1 (3)
O1—C5—C4	116.4 (3)	N1—C21—C20	123.3 (3)
C6—C5—C4	119.7 (3)	N1—C21—H21	118.4
C7—C6—C5	122.5 (3)	C20—C21—H21	118.4
C7—C6—H6	118.7	O5—C22—N2	123.7 (4)
C5—C6—H6	118.7	O5—C22—C20	118.8 (3)
O2—C7—C6	129.7 (3)	N2—C22—C20	117.4 (3)
O2—C7—C8	112.2 (2)	N2—C23—C24	108.1 (8)
C6—C7—C8	118.1 (3)	N2—C23—H23A	110.1
F2—C8—F3	103.8 (4)	C24—C23—H23A	110.1
F2—C8—F1	108.3 (4)	N2—C23—H23B	110.1
F3—C8—F1	104.5 (4)	C24—C23—H23B	110.1
F2—C8—C7	111.5 (3)	H23A—C23—H23B	108.4
F3—C8—C7	112.6 (3)	C23—C24—H24A	109.5
F1—C8—C7	115.2 (3)	C23—C24—H24B	109.5
C10—C9—S2	114.3 (8)	H24A—C24—H24B	109.5
C10—C9—H9	122.8	C23—C24—H24C	109.5
S2—C9—H9	122.8	H24A—C24—H24C	109.5
C9—C10—C11	110.2 (12)	H24B—C24—H24C	109.5
C9—C10—H10	124.9	N2—C25—C26	111.8 (5)
C11—C10—H10	124.9	N2—C25—H25A	109.3
C12—C11—C10	116.1 (12)	C26—C25—H25A	109.3
C12—C11—H11	122.0	N2—C25—H25B	109.3
C10—C11—H11	122.0	C26—C25—H25B	109.3
C10'—C9'—S2'	113 (2)	H25A—C25—H25B	107.9
C10'—C9'—H9'	123.4	C25—C26—H26A	109.5
S2'—C9'—H9'	123.4	C25—C26—H26B	109.5
C9'—C10'—C11'	106 (2)	H26A—C26—H26B	109.5
C9'—C10'—H10'	126.9	C25—C26—H26C	109.5
C11'—C10'—H10'	126.9	H26A—C26—H26C	109.5
C10'—C11'—C12	122 (2)	H26B—C26—H26C	109.5

O2—Cu1—O1—C5	−11.0 (2)	C10'—C11'—C12—C11	−3.7 (9)
O3—Cu1—O1—C5	−178.3 (2)	C10'—C11'—C12—C13	166.2 (9)
N1—Cu1—O1—C5	87.3 (2)	C10'—C11'—C12—S2'	0.7 (6)
O4—Cu1—O2—C7	177.2 (2)	C10'—C11'—C12—S2	−137 (3)
O1—Cu1—O2—C7	5.6 (2)	C9'—S2'—C12—C11	27 (4)
O3—Cu1—O2—C7	86.7 (4)	C9'—S2'—C12—C11'	−0.4 (4)
N1—Cu1—O2—C7	−85.5 (2)	C9'—S2'—C12—C13	−168.8 (7)
O4—Cu1—O3—C13	5.1 (3)	C9'—S2'—C12—S2	13.4 (6)
O1—Cu1—O3—C13	176.9 (3)	C9—S2—C12—C11	0.3 (4)
O2—Cu1—O3—C13	95.1 (5)	C9—S2—C12—C11'	50 (2)
N1—Cu1—O3—C13	−92.7 (3)	C9—S2—C12—C13	−175.1 (4)
O2—Cu1—O4—C15	−172.3 (3)	C9—S2—C12—S2'	2.6 (5)
O3—Cu1—O4—C15	−5.2 (3)	Cu1—O3—C13—C14	−2.5 (5)
N1—Cu1—O4—C15	89.6 (3)	Cu1—O3—C13—C12	178.7 (2)
O4—Cu1—N1—C17	23.0 (2)	C11—C12—C13—O3	−7.5 (6)
O1—Cu1—N1—C17	−158.0 (2)	C11'—C12—C13—O3	−174.7 (9)
O2—Cu1—N1—C17	−65.8 (2)	S2'—C12—C13—O3	−10.7 (6)
O3—Cu1—N1—C17	115.9 (2)	S2—C12—C13—O3	167.0 (3)
O4—Cu1—N1—C21	−162.3 (2)	C11—C12—C13—C14	173.7 (5)
O1—Cu1—N1—C21	16.8 (2)	C11'—C12—C13—C14	6.5 (10)
O2—Cu1—N1—C21	108.9 (2)	S2'—C12—C13—C14	170.5 (5)
O3—Cu1—N1—C21	−69.3 (2)	S2—C12—C13—C14	−11.8 (5)
C4—S1—C1—C2	−0.1 (3)	O3—C13—C14—C15	−1.8 (6)
S1—C1—C2—C3	−0.9 (5)	C12—C13—C14—C15	176.9 (4)
C1—C2—C3—C4	1.6 (5)	Cu1—O4—C15—C14	3.2 (5)
C2—C3—C4—C5	−177.9 (3)	Cu1—O4—C15—C16	179.6 (2)
C2—C3—C4—S1	−1.6 (4)	C13—C14—C15—O4	1.4 (6)
C1—S1—C4—C3	1.0 (3)	C13—C14—C15—C16	−174.9 (3)
C1—S1—C4—C5	177.7 (3)	O4—C15—C16—F5	43.8 (4)
Cu1—O1—C5—C6	11.2 (4)	C14—C15—C16—F5	−139.3 (4)
Cu1—O1—C5—C4	−167.59 (18)	O4—C15—C16—F4	−75.6 (4)
C3—C4—C5—O1	−179.8 (3)	C14—C15—C16—F4	101.3 (4)
S1—C4—C5—O1	4.1 (4)	O4—C15—C16—F6	165.0 (3)
C3—C4—C5—C6	1.3 (5)	C14—C15—C16—F6	−18.1 (5)
S1—C4—C5—C6	−174.7 (2)	C21—N1—C17—C18	0.6 (5)
O1—C5—C6—C7	−3.1 (5)	Cu1—N1—C17—C18	175.4 (2)
C4—C5—C6—C7	175.7 (3)	N1—C17—C18—C19	−1.3 (5)
Cu1—O2—C7—C6	−0.4 (5)	C17—C18—C19—C20	0.4 (5)
Cu1—O2—C7—C8	179.1 (2)	C18—C19—C20—C21	1.1 (5)
C5—C6—C7—O2	−2.7 (5)	C18—C19—C20—C22	177.1 (3)
C5—C6—C7—C8	177.8 (3)	C17—N1—C21—C20	1.1 (5)
O2—C7—C8—F2	65.6 (5)	Cu1—N1—C21—C20	−174.0 (2)
C6—C7—C8—F2	−114.9 (4)	C19—C20—C21—N1	−1.9 (5)
O2—C7—C8—F3	−50.6 (4)	C22—C20—C21—N1	−178.0 (3)
C6—C7—C8—F3	128.9 (4)	C23—N2—C22—O5	−174.8 (6)
O2—C7—C8—F1	−170.4 (4)	C25—N2—C22—O5	2.2 (7)
C6—C7—C8—F1	9.1 (5)	C23—N2—C22—C20	4.3 (8)
C12—S2—C9—C10	−0.12 (18)	C25—N2—C22—C20	−178.7 (5)
S2—C9—C10—C11	−0.1 (2)	C21—C20—C22—O5	92.2 (4)
C9—C10—C11—C12	0.3 (5)	C19—C20—C22—O5	−83.7 (5)
C12—S2'—C9'—C10'	0.14 (19)	C21—C20—C22—N2	−86.9 (5)
S2'—C9'—C10'—C11'	0.2 (2)	C19—C20—C22—N2	97.2 (5)
C9'—C10'—C11'—C12	−0.6 (5)	C22—N2—C23—C24	−97.6 (7)
C10—C11—C12—C11'	−14.3 (9)	C25—N2—C23—C24	85.4 (7)
C10—C11—C12—C13	174.7 (5)	C22—N2—C25—C26	−97.1 (7)
C10—C11—C12—S2'	−168 (4)	C23—N2—C25—C26	80.1 (8)
C10—C11—C12—S2	−0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.93	2.49	3.358 (7)	156
C19—H19···O5ⁱⁱ	0.93	2.56	3.338 (6)	141
C24—H24C···F1ⁱⁱⁱ	0.96	2.36	3.233 (13)	151

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₈H₄F₃O₂S)₂(C₁₀H₁₄N₂O)]
M_r	684.12
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.4324 (5), 12.8606 (5), 13.0104 (5)
α, β, γ (°)	62.837 (1), 64.110 (1), 88.783 (1)
V (Å³)	1492.72 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.618, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	16434, 6849, 5423
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.152, 1.05
No. of reflections	6849
No. of parameters	392
No. of restraints	80
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.48

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—O1	1.9432 (19)	Cu1—O4	1.934 (2)
Cu1—O2	1.942 (2)	Cu1—N1	2.262 (2)
Cu1—O3	1.944 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.93	2.49	3.358 (7)	156
C19—H19···O5ⁱⁱ	0.93	2.56	3.338 (6)	141
C24—H24C···F1ⁱⁱⁱ	0.96	2.36	3.233 (13)	151

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+2.

Acknowledgements

We thank Baku State University and the University of Malaya for supporting this study.

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