{μ-Bis(1-methyl­imidazol-2-yl)methane-κ2N3:N3′}bis­{[(1-methyl­imidazol-2-yl)methane-κ2N3,N3′]copper(I)} bis­(tri­fluoro­methane­sulfonate)

Matsumoto, J.; Kajita, Y.; Masuda, H.

doi:10.1107/S1600536809039622

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1286-m1287

https://doi.org/10.1107/S1600536809039622

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{μ-Bis(1-methylimidazol-2-yl)methane-κ²N³:N^3′}bis{[(1-methylimidazol-2-yl)methane-κ²N³,N^3′]copper(I)} bis(trifluoromethanesulfonate)

Jun Matsumoto,^a Yuji Kajita ^a and Hideki Masuda ^a ^*

^aDepartment of Applied Chemistry, Nagoya Institute of Technology, Showa-ku, Nagoya 466-8555, Japan
^*Correspondence e-mail: masuda.hideki@nitech.ac.jp

(Received 10 August 2009; accepted 29 September 2009; online 3 October 2009)

The title compound, [Cu₂(C₉H₁₂N₄)₃](CF₃SO₃)₂, contains two Cu^I ions, three bis(1-methylimidazol-2-yl)methane (Me₂BIM) ligands, and two trifluoromethanesulfonate anions in the asymmetric unit. Each Cu^I ion has a distorted trigonal-planar geometry and is coordinated by two N atoms from the Me₂BIM ligand and another N atom from the Me₂BIM that acts as a bridging ligand, another N atom of the bridging Me₂BIM being linked to the second Cu^I ion. The imidazole rings of Me₂BIM form intramolecular π–π stacking interactions [centroid–centroid distances = 3.445 (2) and 3.547 (2) Å].

Related literature

For the protonated ligand Me₂BIM, see: Messerle et al. (2003 ). For coordination complexes with one or two Me₂BIM ligands chelating one metal center, see: Elgafi et al. (1999 ); Abuskhuna et al. (2004a ); Burling et al. (2004 ); Kennedy et al. (2007 ); Dabb et al. (2009 ). For Cu^II complexes with two BIM ligands chelating one metal center, see: Place et al. (1998 ). For Ag^I complexes with two BIM ligands bridging two metals, see: Abuskhuna et al. (2004b ). The Me₂BIM ligand was synthesized by modified literature methods (Byers & Canty, 1990 ; Elgafi et al., 1997 ).

Experimental

Crystal data

[Cu₂(C₉H₁₂N₄)₃](CF₃SO₃)₂
M_r = 953.88
Monoclinic, P 2₁ /n
a = 22.5575 (11) Å
b = 7.0307 (3) Å
c = 25.4982 (16) Å
β = 109.118 (2)°
V = 3820.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 173 K
0.20 × 0.15 × 0.15 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: none
29376 measured reflections
8745 independent reflections
6639 reflections with I² > 2σ(I²)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.146
S = 1.14
8745 reflections
515 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N1	2.042 (2)
Cu1—N3	1.958 (3)
Cu1—N9	1.914 (2)
Cu2—N5	2.049 (3)
Cu2—N7	1.935 (3)
Cu2—N11	1.916 (3)

N1—Cu1—N3	95.56 (12)
N1—Cu1—N9	121.37 (12)
N3—Cu1—N9	142.95 (12)
N5—Cu2—N7	93.66 (12)
N5—Cu2—N11	115.27 (11)
N7—Cu2—N11	150.78 (12)

Data collection: CrystalClear (Rigaku, 2007 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039622/bv2129sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039622/bv2129Isup2.hkl

checkCIF report

Comment top

Ligand bis(imidazol-2-yl)methane derivative is a bidentate ligand, either chelating one metal center or bridging two metals. The crystal structures of Cu^II complexes with bis(imidazol-2-yl)methane (BIM) and bis(1-methylimidazol-2-yl)methane (Me₂BIM) have been reported by Place et al. (1998), Abuskhuna et al. (2004a), respectively. In addition, that of Ag^I complex with BIM has been reported by Abuskhuna et al. (2004b). The Cu^II complexes have four- or six-coordinate structure that is coordinated with two Me₂BIM ligands, and the Ag^I complex forms a two-coordinate structure bridged by BIM. The title compound, [(µ-Me₂BIM){Cu(Me₂BIM)}₂](OTf)₂, contains two Cu^I ions, three bis(1-methylimidazol-2-yl)methane (Me₂BIM) ligands, and two trifluoromethanesulfonate anions as an independent unit in the unit cell. Each Cu^I ion has a distorted trigonal planar geometry coordinated with two N atoms from Me₂BIM and one N atom from a bridging Me₂BIM ligand, and an N atom from an additional bridging Me₂BIM which is linked to another Cu^I ion. This is a novel dinuclear Cu^I complex with Me₂BIM. An intramolecular π—π stackings are formed between the imidazol rings; angles between the imidazole ring 1 containing N(1) and the ring 2 containing N(7) and between the ring 3 containing N(5) and the ring 4 containing N(9) are 4.4 (1) and 2.2 (2)°, respectively, and distances of the centroid of plane 1 to plane 2 and that of plane 3 to plane 4 are 3.445 (2) and 3.547 (2) Å, respectively.

Related literature top

For the protonated ligand Me₂BIM, see: Messerle et al. (2003). For coordination complexes with one or two Me₂BIM ligands chelating one metal center, see: Elgafi et al. (1999); Abuskhuna et al. (2004a); Burling et al. (2004); Kennedy et al. (2007); Dabb et al. (2009). For Cu^II complexes with two BIM ligands chelating one metal center, see: Place et al. (1998). For Ag^I complexes with two BIM ligands bridging two metals, see: Abuskhuna et al. (2004b). The Me₂BIM ligand was synthesized by modified literature methods (Byers & Canty, 1990; Elgafi et al., 1997).

Experimental top

Ligand Me₂BIM was synthesized by modifying the literature methods of Byers et al. (1990) and Elgafi et al. (1997). Ligand Me₂BIM (1.13 mmol, 200 mg) in CH₂Cl₂ (4 ml) was added into a MeCN solution (3 ml) of [Cu(MeCN)₄](OTf) (1.15 mmol, 433 mg). The mixture was stirred for 1 h at room temperature in a glovebox ([O₂] < 1 p.p.m. and [H₂O] < 1 p.p.m.). After addition of Et₂O (7 ml), the resulting precipitates were collected by filtration and dried to give an yellow powder in a 65% yield. Single crystals suitable for X-ray crystallographic analysis were obtained by recrystallization from CH₂Cl₂/MeCN/Et₂O.

Structure description top

For the protonated ligand Me₂BIM, see: Messerle et al. (2003). For coordination complexes with one or two Me₂BIM ligands chelating one metal center, see: Elgafi et al. (1999); Abuskhuna et al. (2004a); Burling et al. (2004); Kennedy et al. (2007); Dabb et al. (2009). For Cu^II complexes with two BIM ligands chelating one metal center, see: Place et al. (1998). For Ag^I complexes with two BIM ligands bridging two metals, see: Abuskhuna et al. (2004b). The Me₂BIM ligand was synthesized by modified literature methods (Byers & Canty, 1990; Elgafi et al., 1997).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2007).

Figures top

	Fig. 1. The molecular view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the c axis. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms that are not involved in hydrogen bonding are omitted for clarity.
	Fig. 3. The structures of (A) and (B) show the circumferences of the coppers center, Cu(1) and Cu(2), respectively. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms that are not involved in hydrogen bonding have been omitted for clarity.

{µ-Bis(1-methylimidazol-2-yl)methane-κ²N³:N^3'}bis{[(1- methylimidazol-2-yl)methane-κ²N³,N^3']copper(I)} bis(trifluoromethanesulfonate) top

Crystal data top

[Cu₂(C₉H₁₂N₄)₃](CF₃SO₃)₂	F(000) = 1944.00
M_r = 953.88	D_x = 1.658 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2yn	Cell parameters from 10516 reflections
a = 22.5575 (11) Å	θ = 3.0–27.5°
b = 7.0307 (3) Å	µ = 1.31 mm⁻¹
c = 25.4982 (16) Å	T = 173 K
β = 109.118 (2)°	Block, yellow
V = 3820.9 (3) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.5°
ω scans	h = −29→23
29376 measured reflections	k = −9→9
8745 independent reflections	l = −27→33
6639 reflections with F² > 2σ(F²)

Refinement top

Refinement on F²	0 restraints
R[F² > 2σ(F²)] = 0.055	All H-atom parameters refined
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0583P)² + 1.5952P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
8745 reflections	Δρ_max = 0.58 e Å⁻³
515 parameters	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Cu₂(C₉H₁₂N₄)₃](CF₃SO₃)₂	V = 3820.9 (3) Å³
M_r = 953.88	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 22.5575 (11) Å	µ = 1.31 mm⁻¹
b = 7.0307 (3) Å	T = 173 K
c = 25.4982 (16) Å	0.20 × 0.15 × 0.15 mm
β = 109.118 (2)°

Data collection top

Rigaku Mercury diffractometer	6639 reflections with F² > 2σ(F²)
29376 measured reflections	R_int = 0.039
8745 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.146	All H-atom parameters refined
S = 1.14	Δρ_max = 0.58 e Å⁻³
8745 reflections	Δρ_min = −0.72 e Å⁻³
515 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Cu(1)	0.525378 (19)	0.21542 (6)	0.763364 (17)	0.03927 (13)
Cu(2)	0.52080 (2)	0.61525 (6)	0.716419 (19)	0.04633 (14)
S(1)	0.81822 (4)	0.46106 (15)	0.93194 (4)	0.0487 (2)
S(2)	0.34890 (4)	0.48802 (15)	0.89323 (4)	0.0475 (2)
F(1)	0.87401 (14)	0.6587 (6)	1.02074 (11)	0.1071 (12)
F(2)	0.8022 (2)	0.8084 (4)	0.96078 (14)	0.1107 (12)
F(3)	0.77953 (15)	0.5968 (4)	1.01045 (15)	0.1008 (11)
F(4)	0.38615 (13)	0.1387 (4)	0.91831 (15)	0.0937 (9)
F(5)	0.28917 (13)	0.1643 (4)	0.87220 (15)	0.0935 (10)
F(6)	0.32319 (18)	0.2407 (5)	0.95855 (15)	0.1125 (12)
O(1)	0.83456 (19)	0.2915 (5)	0.96391 (16)	0.0920 (12)
O(2)	0.86351 (15)	0.5278 (5)	0.90881 (12)	0.0753 (9)
O(3)	0.75529 (14)	0.4666 (5)	0.89437 (15)	0.0845 (10)
O(4)	0.40376 (14)	0.5429 (5)	0.93745 (14)	0.0859 (11)
O(5)	0.35806 (17)	0.4652 (4)	0.84099 (12)	0.0761 (9)
O(6)	0.29232 (13)	0.5838 (4)	0.89142 (13)	0.0627 (7)
N(1)	0.54920 (13)	0.1991 (3)	0.84769 (11)	0.0379 (6)
N(2)	0.61408 (14)	0.2013 (4)	0.93364 (11)	0.0406 (6)
N(3)	0.60648 (13)	0.1266 (4)	0.76032 (12)	0.0416 (6)
N(4)	0.70290 (13)	0.0161 (4)	0.78893 (13)	0.0461 (7)
N(5)	0.44244 (14)	0.7760 (4)	0.70788 (12)	0.0413 (6)
N(6)	0.36224 (14)	0.8792 (4)	0.73090 (14)	0.0474 (7)
N(7)	0.55491 (14)	0.6557 (4)	0.79575 (13)	0.0449 (7)
N(8)	0.55692 (15)	0.7111 (4)	0.88142 (13)	0.0489 (7)
N(9)	0.44262 (12)	0.2866 (3)	0.71791 (11)	0.0342 (5)
N(10)	0.36179 (12)	0.3562 (3)	0.64410 (11)	0.0359 (6)
N(11)	0.52866 (13)	0.5210 (4)	0.64851 (12)	0.0409 (6)
N(12)	0.52401 (13)	0.3560 (4)	0.57365 (12)	0.0449 (7)
C(1)	0.51766 (17)	0.2603 (4)	0.88285 (15)	0.0418 (7)
C(2)	0.55684 (17)	0.2619 (5)	0.93589 (15)	0.0441 (8)
C(3)	0.67175 (18)	0.1869 (6)	0.98115 (15)	0.0542 (10)
C(4)	0.60759 (15)	0.1658 (4)	0.87997 (13)	0.0362 (7)
C(5)	0.66238 (16)	0.1017 (5)	0.86426 (14)	0.0410 (7)
C(6)	0.65498 (16)	0.0818 (4)	0.80423 (15)	0.0395 (7)
C(7)	0.62501 (18)	0.0857 (5)	0.71475 (15)	0.0500 (9)
C(8)	0.68394 (18)	0.0176 (6)	0.73197 (16)	0.0536 (9)
C(9)	0.76404 (18)	−0.0461 (7)	0.82589 (18)	0.0656 (12)
C(10)	0.39374 (18)	0.8252 (5)	0.66014 (17)	0.0507 (9)
C(11)	0.34477 (18)	0.8879 (5)	0.67389 (17)	0.0528 (10)
C(12)	0.3231 (2)	0.9282 (6)	0.7644 (2)	0.0670 (12)
C(13)	0.42209 (15)	0.8108 (4)	0.74969 (14)	0.0373 (7)
C(14)	0.45525 (16)	0.7850 (5)	0.81032 (14)	0.0429 (8)
C(15)	0.52150 (16)	0.7159 (4)	0.82688 (14)	0.0401 (7)
C(16)	0.61394 (17)	0.6113 (5)	0.83269 (18)	0.0539 (10)
C(17)	0.61495 (19)	0.6439 (5)	0.88480 (18)	0.0565 (10)
C(18)	0.5355 (2)	0.7561 (6)	0.92820 (17)	0.0621 (11)
C(19)	0.39341 (15)	0.3483 (4)	0.73479 (14)	0.0373 (7)
C(20)	0.34333 (16)	0.3899 (4)	0.68955 (15)	0.0404 (7)
C(21)	0.32136 (18)	0.3793 (5)	0.58651 (15)	0.0524 (9)
C(22)	0.42150 (15)	0.2945 (4)	0.66262 (13)	0.0339 (6)
C(23)	0.45787 (16)	0.2303 (5)	0.62668 (15)	0.0414 (7)
C(24)	0.50238 (15)	0.3732 (5)	0.61708 (14)	0.0377 (7)
C(25)	0.56876 (17)	0.6003 (5)	0.62356 (17)	0.0502 (9)
C(26)	0.56674 (18)	0.4982 (6)	0.57821 (18)	0.0586 (10)
C(27)	0.50716 (19)	0.2054 (6)	0.53201 (17)	0.0612 (11)
C(28)	0.8175 (2)	0.6401 (6)	0.98281 (17)	0.0580 (10)
C(29)	0.3366 (2)	0.2461 (7)	0.9112 (2)	0.0617 (11)
H(3A)	0.6629	0.2203	1.0152	0.065*
H(3B)	0.7032	0.2745	0.9761	0.065*
H(3C)	0.6877	0.0564	0.9841	0.065*
H(9A)	0.7932	−0.0578	0.8048	0.079*
H(9B)	0.7597	−0.1698	0.8420	0.079*
H(9C)	0.7803	0.0474	0.8557	0.079*
H(12A)	0.2814	0.9670	0.7400	0.080*
H(12B)	0.3424	1.0333	0.7894	0.080*
H(12C)	0.3190	0.8174	0.7863	0.080*
H(18A)	0.5687	0.7257	0.9630	0.074*
H(18B)	0.4980	0.6811	0.9254	0.074*
H(18C)	0.5254	0.8919	0.9275	0.074*
H(21A)	0.3013	0.5046	0.5818	0.063*
H(21B)	0.2891	0.2800	0.5772	0.063*
H(21C)	0.3466	0.3688	0.5619	0.063*
H(27A)	0.5262	0.2318	0.5033	0.073*
H(27B)	0.4614	0.2002	0.5151	0.073*
H(27C)	0.5226	0.0832	0.5497	0.073*
H(5A)	0.6759	−0.0232	0.8821	0.049*
H(5B)	0.6971	0.1923	0.8807	0.049*
H(14A)	0.4308	0.6940	0.8247	0.051*
H(14B)	0.4550	0.9084	0.8289	0.051*
H(23A)	0.4279	0.1925	0.5902	0.050*
H(23B)	0.4820	0.1155	0.6436	0.050*
H(1)	0.4747	0.2960	0.8714	0.050*
H(2)	0.5470	0.2973	0.9680	0.053*
H(7)	0.5998	0.1031	0.6771	0.060*
H(8)	0.7077	−0.0216	0.7093	0.064*
H(10)	0.3950	0.8157	0.6234	0.061*
H(11)	0.3056	0.9303	0.6491	0.063*
H(16)	0.6482	0.5650	0.8226	0.065*
H(17)	0.6494	0.6240	0.9178	0.068*
H(19)	0.3946	0.3597	0.7722	0.045*
H(20)	0.3034	0.4337	0.6893	0.049*
H(25)	0.5939	0.7100	0.6364	0.060*
H(26)	0.5904	0.5207	0.5541	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu(1)	0.0346 (2)	0.0410 (2)	0.0372 (2)	−0.00196 (17)	0.00483 (17)	0.00048 (18)
Cu(2)	0.0499 (2)	0.0403 (2)	0.0498 (2)	−0.00973 (19)	0.0176 (2)	−0.0088 (2)
S(1)	0.0388 (4)	0.0551 (5)	0.0516 (5)	0.0004 (4)	0.0142 (4)	0.0076 (4)
S(2)	0.0425 (5)	0.0587 (5)	0.0429 (5)	−0.0080 (4)	0.0163 (4)	−0.0085 (4)
F(1)	0.0700 (18)	0.202 (3)	0.0457 (15)	−0.017 (2)	0.0142 (13)	−0.0382 (19)
F(2)	0.188 (3)	0.0547 (17)	0.085 (2)	0.000 (2)	0.039 (2)	−0.0057 (16)
F(3)	0.103 (2)	0.100 (2)	0.140 (2)	−0.0088 (18)	0.095 (2)	−0.017 (2)
F(4)	0.0673 (18)	0.079 (2)	0.135 (2)	0.0213 (15)	0.0337 (18)	0.0262 (19)
F(5)	0.0582 (16)	0.0613 (16)	0.148 (2)	−0.0143 (13)	0.0164 (17)	−0.0128 (18)
F(6)	0.129 (2)	0.132 (3)	0.104 (2)	0.016 (2)	0.076 (2)	0.050 (2)
O(1)	0.127 (3)	0.072 (2)	0.095 (2)	0.047 (2)	0.061 (2)	0.038 (2)
O(2)	0.077 (2)	0.111 (2)	0.0459 (16)	−0.0351 (19)	0.0308 (14)	−0.0173 (17)
O(3)	0.0433 (16)	0.079 (2)	0.109 (2)	−0.0067 (15)	−0.0063 (16)	−0.019 (2)
O(4)	0.0546 (19)	0.105 (2)	0.084 (2)	−0.0264 (18)	0.0035 (16)	−0.033 (2)
O(5)	0.107 (2)	0.084 (2)	0.0552 (17)	0.0041 (19)	0.0506 (18)	0.0037 (16)
O(6)	0.0498 (16)	0.0592 (17)	0.078 (2)	−0.0022 (13)	0.0193 (14)	−0.0176 (15)
N(1)	0.0391 (15)	0.0367 (14)	0.0355 (14)	−0.0044 (11)	0.0091 (12)	−0.0003 (12)
N(2)	0.0475 (16)	0.0373 (15)	0.0316 (14)	−0.0037 (12)	0.0055 (12)	0.0020 (12)
N(3)	0.0387 (15)	0.0454 (16)	0.0394 (15)	0.0008 (12)	0.0109 (12)	0.0008 (13)
N(4)	0.0367 (15)	0.0469 (17)	0.0494 (17)	0.0066 (13)	0.0071 (13)	0.0001 (14)
N(5)	0.0436 (16)	0.0340 (14)	0.0393 (16)	−0.0042 (12)	0.0039 (12)	−0.0025 (12)
N(6)	0.0399 (16)	0.0362 (15)	0.063 (2)	−0.0016 (12)	0.0133 (14)	0.0012 (14)
N(7)	0.0379 (15)	0.0330 (14)	0.0543 (18)	−0.0078 (12)	0.0023 (13)	−0.0037 (13)
N(8)	0.0566 (19)	0.0388 (16)	0.0391 (16)	−0.0131 (14)	−0.0010 (14)	0.0003 (13)
N(9)	0.0340 (13)	0.0348 (14)	0.0314 (13)	−0.0053 (11)	0.0075 (11)	−0.0033 (11)
N(10)	0.0323 (13)	0.0367 (14)	0.0350 (14)	−0.0013 (11)	0.0057 (11)	−0.0002 (11)
N(11)	0.0336 (14)	0.0384 (15)	0.0484 (16)	−0.0036 (11)	0.0104 (12)	0.0030 (13)
N(12)	0.0333 (14)	0.0611 (19)	0.0413 (16)	0.0005 (13)	0.0135 (12)	−0.0041 (14)
C(1)	0.0435 (19)	0.0390 (18)	0.0415 (19)	−0.0008 (14)	0.0119 (15)	−0.0008 (15)
C(2)	0.053 (2)	0.0401 (18)	0.0392 (19)	−0.0049 (15)	0.0150 (16)	0.0008 (15)
C(3)	0.054 (2)	0.063 (2)	0.0341 (19)	−0.0035 (19)	−0.0005 (16)	0.0042 (18)
C(4)	0.0431 (18)	0.0308 (15)	0.0318 (16)	−0.0065 (13)	0.0082 (13)	0.0010 (13)
C(5)	0.0374 (17)	0.0411 (18)	0.0385 (18)	−0.0034 (14)	0.0045 (14)	0.0005 (15)
C(6)	0.0364 (17)	0.0347 (16)	0.0433 (18)	−0.0033 (13)	0.0074 (14)	−0.0026 (14)
C(7)	0.047 (2)	0.063 (2)	0.0380 (19)	0.0073 (18)	0.0116 (16)	0.0002 (17)
C(8)	0.048 (2)	0.066 (2)	0.048 (2)	0.0044 (19)	0.0182 (17)	−0.0013 (19)
C(9)	0.042 (2)	0.085 (3)	0.063 (2)	0.019 (2)	0.0084 (19)	−0.000 (2)
C(10)	0.053 (2)	0.0403 (19)	0.046 (2)	−0.0089 (16)	−0.0012 (17)	0.0015 (16)
C(11)	0.044 (2)	0.0393 (19)	0.058 (2)	−0.0037 (16)	−0.0056 (17)	0.0087 (18)
C(12)	0.052 (2)	0.056 (2)	0.100 (3)	0.0067 (19)	0.035 (2)	0.013 (2)
C(13)	0.0368 (17)	0.0288 (15)	0.0432 (18)	−0.0054 (12)	0.0091 (14)	0.0008 (14)
C(14)	0.0447 (19)	0.0423 (19)	0.0395 (18)	−0.0092 (15)	0.0109 (15)	−0.0065 (15)
C(15)	0.0422 (18)	0.0312 (16)	0.0391 (18)	−0.0103 (13)	0.0027 (14)	−0.0001 (14)
C(16)	0.0362 (19)	0.0389 (19)	0.072 (2)	−0.0077 (15)	−0.0022 (18)	0.0017 (19)
C(17)	0.049 (2)	0.043 (2)	0.056 (2)	−0.0084 (17)	−0.0129 (18)	0.0064 (18)
C(18)	0.081 (3)	0.055 (2)	0.040 (2)	−0.018 (2)	0.006 (2)	−0.0049 (18)
C(19)	0.0357 (17)	0.0369 (17)	0.0399 (17)	−0.0049 (13)	0.0130 (14)	−0.0053 (14)
C(20)	0.0369 (17)	0.0372 (18)	0.048 (2)	−0.0017 (14)	0.0150 (15)	−0.0017 (15)
C(21)	0.049 (2)	0.057 (2)	0.042 (2)	−0.0015 (18)	0.0023 (16)	0.0024 (18)
C(22)	0.0351 (16)	0.0311 (15)	0.0331 (16)	−0.0044 (12)	0.0078 (13)	−0.0045 (13)
C(23)	0.0411 (18)	0.0405 (18)	0.0440 (19)	−0.0058 (14)	0.0159 (15)	−0.0092 (15)
C(24)	0.0314 (16)	0.0441 (19)	0.0356 (17)	0.0008 (13)	0.0083 (13)	−0.0019 (14)
C(25)	0.0355 (18)	0.054 (2)	0.064 (2)	−0.0065 (16)	0.0199 (17)	−0.0021 (19)
C(26)	0.042 (2)	0.080 (3)	0.061 (2)	−0.007 (2)	0.0266 (19)	0.000 (2)
C(27)	0.047 (2)	0.089 (3)	0.051 (2)	−0.002 (2)	0.0214 (18)	−0.022 (2)
C(28)	0.059 (2)	0.068 (2)	0.048 (2)	−0.003 (2)	0.0191 (19)	0.001 (2)
C(29)	0.048 (2)	0.071 (2)	0.066 (2)	0.001 (2)	0.018 (2)	0.009 (2)

Geometric parameters (Å, º) top

Cu(1)—N(1)	2.042 (2)	N(12)—C(27)	1.459 (5)
Cu(1)—N(3)	1.958 (3)	C(1)—C(2)	1.352 (4)
Cu(1)—N(9)	1.914 (2)	C(4)—C(5)	1.488 (5)
Cu(2)—N(5)	2.049 (3)	C(5)—C(6)	1.491 (5)
Cu(2)—N(7)	1.935 (3)	C(7)—C(8)	1.344 (5)
Cu(2)—N(11)	1.916 (3)	C(10)—C(11)	1.338 (6)
S(1)—O(1)	1.423 (3)	C(13)—C(14)	1.492 (4)
S(1)—O(2)	1.416 (3)	C(14)—C(15)	1.495 (4)
S(1)—O(3)	1.430 (2)	C(16)—C(17)	1.341 (6)
S(1)—C(28)	1.811 (4)	C(19)—C(20)	1.356 (4)
S(2)—O(4)	1.427 (2)	C(22)—C(23)	1.486 (5)
S(2)—O(5)	1.422 (3)	C(23)—C(24)	1.496 (5)
S(2)—O(6)	1.430 (3)	C(25)—C(26)	1.349 (6)
S(2)—C(29)	1.807 (5)	C(1)—H(1)	0.950
F(1)—C(28)	1.331 (4)	C(2)—H(2)	0.950
F(2)—C(28)	1.307 (5)	C(3)—H(3A)	0.980
F(3)—C(28)	1.310 (6)	C(3)—H(3B)	0.980
F(4)—C(29)	1.312 (5)	C(3)—H(3C)	0.980
F(5)—C(29)	1.329 (4)	C(5)—H(5A)	0.990
F(6)—C(29)	1.337 (6)	C(5)—H(5B)	0.990
N(1)—C(1)	1.383 (5)	C(7)—H(7)	0.950
N(1)—C(4)	1.326 (3)	C(8)—H(8)	0.950
N(2)—C(2)	1.378 (5)	C(9)—H(9A)	0.980
N(2)—C(3)	1.462 (4)	C(9)—H(9B)	0.980
N(2)—C(4)	1.351 (4)	C(9)—H(9C)	0.980
N(3)—C(6)	1.322 (3)	C(10)—H(10)	0.950
N(3)—C(7)	1.388 (5)	C(11)—H(11)	0.950
N(4)—C(6)	1.346 (5)	C(12)—H(12A)	0.980
N(4)—C(8)	1.373 (5)	C(12)—H(12B)	0.980
N(4)—C(9)	1.459 (4)	C(12)—H(12C)	0.980
N(5)—C(10)	1.390 (4)	C(14)—H(14A)	0.990
N(5)—C(13)	1.314 (5)	C(14)—H(14B)	0.990
N(6)—C(11)	1.377 (5)	C(16)—H(16)	0.950
N(6)—C(12)	1.458 (6)	C(17)—H(17)	0.950
N(6)—C(13)	1.364 (4)	C(18)—H(18A)	0.980
N(7)—C(15)	1.330 (5)	C(18)—H(18B)	0.980
N(7)—C(16)	1.392 (4)	C(18)—H(18C)	0.980
N(8)—C(15)	1.359 (4)	C(19)—H(19)	0.950
N(8)—C(17)	1.368 (5)	C(20)—H(20)	0.950
N(8)—C(18)	1.461 (6)	C(21)—H(21A)	0.980
N(9)—C(19)	1.385 (4)	C(21)—H(21B)	0.980
N(9)—C(22)	1.333 (4)	C(21)—H(21C)	0.980
N(10)—C(20)	1.374 (5)	C(23)—H(23A)	0.990
N(10)—C(21)	1.462 (4)	C(23)—H(23B)	0.990
N(10)—C(22)	1.345 (4)	C(25)—H(25)	0.950
N(11)—C(24)	1.327 (4)	C(26)—H(26)	0.950
N(11)—C(25)	1.382 (5)	C(27)—H(27A)	0.980
N(12)—C(24)	1.354 (5)	C(27)—H(27B)	0.980
N(12)—C(26)	1.367 (5)	C(27)—H(27C)	0.980

N(1)—Cu(1)—N(3)	95.56 (12)	S(1)—C(28)—F(1)	110.9 (3)
N(1)—Cu(1)—N(9)	121.37 (12)	S(1)—C(28)—F(2)	112.6 (3)
N(3)—Cu(1)—N(9)	142.95 (12)	S(1)—C(28)—F(3)	112.6 (3)
N(5)—Cu(2)—N(7)	93.66 (12)	F(1)—C(28)—F(2)	106.2 (3)
N(5)—Cu(2)—N(11)	115.27 (11)	F(1)—C(28)—F(3)	105.7 (3)
N(7)—Cu(2)—N(11)	150.78 (12)	F(2)—C(28)—F(3)	108.3 (4)
O(1)—S(1)—O(2)	115.4 (2)	S(2)—C(29)—F(4)	112.4 (3)
O(1)—S(1)—O(3)	114.9 (2)	S(2)—C(29)—F(5)	111.7 (3)
O(1)—S(1)—C(28)	103.5 (2)	S(2)—C(29)—F(6)	110.8 (3)
O(2)—S(1)—O(3)	113.9 (2)	F(4)—C(29)—F(5)	107.1 (3)
O(2)—S(1)—C(28)	104.2 (2)	F(4)—C(29)—F(6)	107.1 (3)
O(3)—S(1)—C(28)	102.8 (2)	F(5)—C(29)—F(6)	107.4 (4)
O(4)—S(2)—O(5)	114.6 (2)	N(1)—C(1)—H(1)	124.9
O(4)—S(2)—O(6)	115.6 (2)	C(2)—C(1)—H(1)	124.9
O(4)—S(2)—C(29)	102.7 (2)	N(2)—C(2)—H(2)	127.2
O(5)—S(2)—O(6)	115.13 (19)	C(1)—C(2)—H(2)	127.2
O(5)—S(2)—C(29)	102.3 (2)	N(2)—C(3)—H(3A)	109.5
O(6)—S(2)—C(29)	103.9 (2)	N(2)—C(3)—H(3B)	109.5
Cu(1)—N(1)—C(1)	130.7 (2)	N(2)—C(3)—H(3C)	109.5
Cu(1)—N(1)—C(4)	121.9 (2)	H(3A)—C(3)—H(3B)	109.5
C(1)—N(1)—C(4)	105.7 (2)	H(3A)—C(3)—H(3C)	109.5
C(2)—N(2)—C(3)	125.3 (3)	H(3B)—C(3)—H(3C)	109.5
C(2)—N(2)—C(4)	107.9 (2)	C(4)—C(5)—H(5A)	107.6
C(3)—N(2)—C(4)	126.7 (3)	C(4)—C(5)—H(5B)	107.6
Cu(1)—N(3)—C(6)	124.5 (2)	C(6)—C(5)—H(5A)	107.6
Cu(1)—N(3)—C(7)	129.8 (2)	C(6)—C(5)—H(5B)	107.6
C(6)—N(3)—C(7)	105.5 (3)	H(5A)—C(5)—H(5B)	107.1
C(6)—N(4)—C(8)	107.6 (2)	N(3)—C(7)—H(7)	125.1
C(6)—N(4)—C(9)	126.5 (3)	C(8)—C(7)—H(7)	125.1
C(8)—N(4)—C(9)	125.9 (3)	N(4)—C(8)—H(8)	126.9
Cu(2)—N(5)—C(10)	129.6 (2)	C(7)—C(8)—H(8)	126.8
Cu(2)—N(5)—C(13)	122.3 (2)	N(4)—C(9)—H(9A)	109.5
C(10)—N(5)—C(13)	106.2 (3)	N(4)—C(9)—H(9B)	109.5
C(11)—N(6)—C(12)	126.1 (3)	N(4)—C(9)—H(9C)	109.5
C(11)—N(6)—C(13)	107.1 (3)	H(9A)—C(9)—H(9B)	109.5
C(12)—N(6)—C(13)	126.7 (3)	H(9A)—C(9)—H(9C)	109.5
Cu(2)—N(7)—C(15)	124.2 (2)	H(9B)—C(9)—H(9C)	109.5
Cu(2)—N(7)—C(16)	129.7 (3)	N(5)—C(10)—H(10)	125.2
C(15)—N(7)—C(16)	105.7 (3)	C(11)—C(10)—H(10)	125.2
C(15)—N(8)—C(17)	107.6 (3)	N(6)—C(11)—H(11)	126.7
C(15)—N(8)—C(18)	126.1 (3)	C(10)—C(11)—H(11)	126.7
C(17)—N(8)—C(18)	126.1 (3)	N(6)—C(12)—H(12A)	109.5
Cu(1)—N(9)—C(19)	128.0 (2)	N(6)—C(12)—H(12B)	109.5
Cu(1)—N(9)—C(22)	126.2 (2)	N(6)—C(12)—H(12C)	109.5
C(19)—N(9)—C(22)	105.7 (2)	H(12A)—C(12)—H(12B)	109.5
C(20)—N(10)—C(21)	124.5 (2)	H(12A)—C(12)—H(12C)	109.5
C(20)—N(10)—C(22)	107.7 (2)	H(12B)—C(12)—H(12C)	109.5
C(21)—N(10)—C(22)	127.7 (3)	C(13)—C(14)—H(14A)	108.1
Cu(2)—N(11)—C(24)	131.4 (2)	C(13)—C(14)—H(14B)	108.1
Cu(2)—N(11)—C(25)	123.0 (2)	C(15)—C(14)—H(14A)	108.1
C(24)—N(11)—C(25)	105.5 (3)	C(15)—C(14)—H(14B)	108.2
C(24)—N(12)—C(26)	107.3 (3)	H(14A)—C(14)—H(14B)	107.3
C(24)—N(12)—C(27)	125.6 (3)	N(7)—C(16)—H(16)	125.2
C(26)—N(12)—C(27)	126.9 (3)	C(17)—C(16)—H(16)	125.2
N(1)—C(1)—C(2)	110.2 (3)	N(8)—C(17)—H(17)	126.5
N(2)—C(2)—C(1)	105.7 (3)	C(16)—C(17)—H(17)	126.5
N(1)—C(4)—N(2)	110.6 (3)	N(8)—C(18)—H(18A)	109.5
N(1)—C(4)—C(5)	129.1 (3)	N(8)—C(18)—H(18B)	109.5
N(2)—C(4)—C(5)	120.3 (2)	N(8)—C(18)—H(18C)	109.5
C(4)—C(5)—C(6)	118.8 (2)	H(18A)—C(18)—H(18B)	109.5
N(3)—C(6)—N(4)	110.9 (3)	H(18A)—C(18)—H(18C)	109.5
N(3)—C(6)—C(5)	129.1 (3)	H(18B)—C(18)—H(18C)	109.5
N(4)—C(6)—C(5)	120.0 (2)	N(9)—C(19)—H(19)	125.3
N(3)—C(7)—C(8)	109.7 (3)	C(20)—C(19)—H(19)	125.3
N(4)—C(8)—C(7)	106.3 (3)	N(10)—C(20)—H(20)	126.8
N(5)—C(10)—C(11)	109.6 (3)	C(19)—C(20)—H(20)	126.8
N(6)—C(11)—C(10)	106.6 (3)	N(10)—C(21)—H(21A)	109.5
N(5)—C(13)—N(6)	110.4 (2)	N(10)—C(21)—H(21B)	109.5
N(5)—C(13)—C(14)	128.9 (3)	N(10)—C(21)—H(21C)	109.5
N(6)—C(13)—C(14)	120.6 (3)	H(21A)—C(21)—H(21B)	109.5
C(13)—C(14)—C(15)	116.6 (3)	H(21A)—C(21)—H(21C)	109.5
N(7)—C(15)—N(8)	110.2 (3)	H(21B)—C(21)—H(21C)	109.5
N(7)—C(15)—C(14)	130.1 (2)	C(22)—C(23)—H(23A)	108.4
N(8)—C(15)—C(14)	119.7 (3)	C(22)—C(23)—H(23B)	108.4
N(7)—C(16)—C(17)	109.5 (3)	C(24)—C(23)—H(23A)	108.4
N(8)—C(17)—C(16)	106.9 (3)	C(24)—C(23)—H(23B)	108.4
N(9)—C(19)—C(20)	109.4 (3)	H(23A)—C(23)—H(23B)	107.4
N(10)—C(20)—C(19)	106.4 (3)	N(11)—C(25)—H(25)	125.2
N(9)—C(22)—N(10)	110.8 (3)	C(26)—C(25)—H(25)	125.2
N(9)—C(22)—C(23)	124.1 (2)	N(12)—C(26)—H(26)	126.7
N(10)—C(22)—C(23)	125.0 (2)	C(25)—C(26)—H(26)	126.7
C(22)—C(23)—C(24)	115.6 (2)	N(12)—C(27)—H(27A)	109.5
N(11)—C(24)—N(12)	110.8 (3)	N(12)—C(27)—H(27B)	109.5
N(11)—C(24)—C(23)	128.2 (3)	N(12)—C(27)—H(27C)	109.5
N(12)—C(24)—C(23)	121.0 (3)	H(27A)—C(27)—H(27B)	109.5
N(11)—C(25)—C(26)	109.7 (3)	H(27A)—C(27)—H(27C)	109.5
N(12)—C(26)—C(25)	106.7 (4)	H(27B)—C(27)—H(27C)	109.5

N(1)—Cu(1)—N(3)—C(6)	−1.1 (2)	Cu(2)—N(5)—C(10)—C(11)	163.8 (2)
N(1)—Cu(1)—N(3)—C(7)	174.5 (3)	Cu(2)—N(5)—C(13)—N(6)	−165.2 (2)
N(3)—Cu(1)—N(1)—C(1)	171.7 (2)	Cu(2)—N(5)—C(13)—C(14)	14.8 (4)
N(3)—Cu(1)—N(1)—C(4)	9.0 (2)	C(10)—N(5)—C(13)—N(6)	0.4 (3)
N(1)—Cu(1)—N(9)—C(19)	5.9 (3)	C(10)—N(5)—C(13)—C(14)	−179.6 (3)
N(1)—Cu(1)—N(9)—C(22)	−177.2 (2)	C(13)—N(5)—C(10)—C(11)	−0.3 (4)
N(9)—Cu(1)—N(1)—C(1)	−11.5 (3)	C(12)—N(6)—C(11)—C(10)	−178.1 (3)
N(9)—Cu(1)—N(1)—C(4)	−174.2 (2)	C(11)—N(6)—C(13)—N(5)	−0.3 (3)
N(3)—Cu(1)—N(9)—C(19)	−179.4 (2)	C(11)—N(6)—C(13)—C(14)	179.7 (3)
N(3)—Cu(1)—N(9)—C(22)	−2.5 (3)	C(13)—N(6)—C(11)—C(10)	0.1 (3)
N(9)—Cu(1)—N(3)—C(6)	−176.5 (2)	C(12)—N(6)—C(13)—N(5)	177.9 (3)
N(9)—Cu(1)—N(3)—C(7)	−1.0 (4)	C(12)—N(6)—C(13)—C(14)	−2.2 (5)
N(5)—Cu(2)—N(7)—C(15)	17.9 (2)	Cu(2)—N(7)—C(15)—N(8)	173.6 (2)
N(5)—Cu(2)—N(7)—C(16)	−170.1 (3)	Cu(2)—N(7)—C(15)—C(14)	−7.2 (5)
N(7)—Cu(2)—N(5)—C(10)	176.6 (3)	Cu(2)—N(7)—C(16)—C(17)	−172.7 (2)
N(7)—Cu(2)—N(5)—C(13)	−21.6 (2)	C(15)—N(7)—C(16)—C(17)	0.4 (4)
N(5)—Cu(2)—N(11)—C(24)	−80.3 (3)	C(16)—N(7)—C(15)—N(8)	0.0 (3)
N(5)—Cu(2)—N(11)—C(25)	102.8 (2)	C(16)—N(7)—C(15)—C(14)	179.2 (3)
N(11)—Cu(2)—N(5)—C(10)	0.8 (3)	C(15)—N(8)—C(17)—C(16)	0.6 (4)
N(11)—Cu(2)—N(5)—C(13)	162.7 (2)	C(17)—N(8)—C(15)—N(7)	−0.4 (4)
N(7)—Cu(2)—N(11)—C(24)	108.3 (3)	C(17)—N(8)—C(15)—C(14)	−179.7 (3)
N(7)—Cu(2)—N(11)—C(25)	−68.6 (3)	C(18)—N(8)—C(15)—N(7)	−176.3 (3)
N(11)—Cu(2)—N(7)—C(15)	−169.9 (2)	C(18)—N(8)—C(15)—C(14)	4.4 (5)
N(11)—Cu(2)—N(7)—C(16)	2.1 (4)	C(18)—N(8)—C(17)—C(16)	176.5 (3)
O(1)—S(1)—C(28)—F(1)	62.2 (3)	Cu(1)—N(9)—C(19)—C(20)	178.1 (2)
O(1)—S(1)—C(28)—F(2)	−179.0 (3)	Cu(1)—N(9)—C(22)—N(10)	−177.9 (2)
O(1)—S(1)—C(28)—F(3)	−56.2 (3)	Cu(1)—N(9)—C(22)—C(23)	6.2 (4)
O(2)—S(1)—C(28)—F(1)	−58.9 (3)	C(19)—N(9)—C(22)—N(10)	−0.5 (3)
O(2)—S(1)—C(28)—F(2)	59.9 (3)	C(19)—N(9)—C(22)—C(23)	−176.4 (3)
O(2)—S(1)—C(28)—F(3)	−177.2 (2)	C(22)—N(9)—C(19)—C(20)	0.8 (3)
O(3)—S(1)—C(28)—F(1)	−178.0 (3)	C(21)—N(10)—C(20)—C(19)	178.7 (3)
O(3)—S(1)—C(28)—F(2)	−59.1 (4)	C(20)—N(10)—C(22)—N(9)	0.0 (3)
O(3)—S(1)—C(28)—F(3)	63.7 (3)	C(20)—N(10)—C(22)—C(23)	175.9 (3)
O(4)—S(2)—C(29)—F(4)	−55.1 (3)	C(22)—N(10)—C(20)—C(19)	0.5 (3)
O(4)—S(2)—C(29)—F(5)	−175.5 (3)	C(21)—N(10)—C(22)—N(9)	−178.1 (3)
O(4)—S(2)—C(29)—F(6)	64.7 (3)	C(21)—N(10)—C(22)—C(23)	−2.2 (5)
O(5)—S(2)—C(29)—F(4)	64.0 (3)	Cu(2)—N(11)—C(24)—N(12)	−177.3 (2)
O(5)—S(2)—C(29)—F(5)	−56.5 (4)	Cu(2)—N(11)—C(24)—C(23)	−1.0 (5)
O(5)—S(2)—C(29)—F(6)	−176.3 (2)	Cu(2)—N(11)—C(25)—C(26)	176.7 (2)
O(6)—S(2)—C(29)—F(4)	−175.9 (3)	C(24)—N(11)—C(25)—C(26)	−0.9 (3)
O(6)—S(2)—C(29)—F(5)	63.7 (4)	C(25)—N(11)—C(24)—N(12)	−0.0 (3)
O(6)—S(2)—C(29)—F(6)	−56.1 (3)	C(25)—N(11)—C(24)—C(23)	176.2 (3)
Cu(1)—N(1)—C(1)—C(2)	−165.4 (2)	C(24)—N(12)—C(26)—C(25)	−1.4 (4)
Cu(1)—N(1)—C(4)—N(2)	167.0 (2)	C(26)—N(12)—C(24)—N(11)	0.9 (3)
Cu(1)—N(1)—C(4)—C(5)	−11.9 (4)	C(26)—N(12)—C(24)—C(23)	−175.7 (2)
C(1)—N(1)—C(4)—N(2)	0.6 (3)	C(27)—N(12)—C(24)—N(11)	177.4 (3)
C(1)—N(1)—C(4)—C(5)	−178.4 (3)	C(27)—N(12)—C(24)—C(23)	0.9 (4)
C(4)—N(1)—C(1)—C(2)	−0.5 (3)	C(27)—N(12)—C(26)—C(25)	−177.9 (3)
C(3)—N(2)—C(2)—C(1)	177.6 (3)	N(1)—C(1)—C(2)—N(2)	0.3 (4)
C(2)—N(2)—C(4)—N(1)	−0.4 (3)	N(1)—C(4)—C(5)—C(6)	4.6 (5)
C(2)—N(2)—C(4)—C(5)	178.7 (3)	N(2)—C(4)—C(5)—C(6)	−174.2 (3)
C(4)—N(2)—C(2)—C(1)	0.0 (3)	C(4)—C(5)—C(6)—N(3)	5.5 (5)
C(3)—N(2)—C(4)—N(1)	−178.0 (3)	C(4)—C(5)—C(6)—N(4)	−177.0 (3)
C(3)—N(2)—C(4)—C(5)	1.1 (5)	N(3)—C(7)—C(8)—N(4)	−0.2 (3)
Cu(1)—N(3)—C(6)—N(4)	176.7 (2)	N(5)—C(10)—C(11)—N(6)	0.1 (3)
Cu(1)—N(3)—C(6)—C(5)	−5.6 (5)	N(5)—C(13)—C(14)—C(15)	2.1 (5)
Cu(1)—N(3)—C(7)—C(8)	−176.2 (2)	N(6)—C(13)—C(14)—C(15)	−177.9 (2)
C(6)—N(3)—C(7)—C(8)	−0.0 (3)	C(13)—C(14)—C(15)—N(7)	−7.0 (5)
C(7)—N(3)—C(6)—N(4)	0.3 (4)	C(13)—C(14)—C(15)—N(8)	172.1 (3)
C(7)—N(3)—C(6)—C(5)	178.0 (3)	N(7)—C(16)—C(17)—N(8)	−0.6 (4)
C(6)—N(4)—C(8)—C(7)	0.4 (4)	N(9)—C(19)—C(20)—N(10)	−0.8 (3)
C(8)—N(4)—C(6)—N(3)	−0.4 (4)	N(9)—C(22)—C(23)—C(24)	−84.8 (3)
C(8)—N(4)—C(6)—C(5)	−178.3 (3)	N(10)—C(22)—C(23)—C(24)	99.9 (3)
C(9)—N(4)—C(6)—N(3)	179.7 (3)	C(22)—C(23)—C(24)—N(11)	23.6 (4)
C(9)—N(4)—C(6)—C(5)	1.8 (5)	C(22)—C(23)—C(24)—N(12)	−160.4 (2)
C(9)—N(4)—C(8)—C(7)	−179.7 (3)	N(11)—C(25)—C(26)—N(12)	1.4 (4)

Experimental details

Crystal data
Chemical formula	[Cu₂(C₉H₁₂N₄)₃](CF₃SO₃)₂
M_r	953.88
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	22.5575 (11), 7.0307 (3), 25.4982 (16)
β (°)	109.118 (2)
V (Å³)	3820.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Rigaku Mercury
Absorption correction	–
No. of measured, independent and observed [F² > 2σ(F²)] reflections	29376, 8745, 6639
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.146, 1.14
No. of reflections	8745
No. of parameters	515
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.72

Computer programs: CrystalClear (Rigaku, 2007), CrystalStructure (Rigaku, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Cu(1)—N(1)	2.042 (2)	Cu(2)—N(5)	2.049 (3)
Cu(1)—N(3)	1.958 (3)	Cu(2)—N(7)	1.935 (3)
Cu(1)—N(9)	1.914 (2)	Cu(2)—N(11)	1.916 (3)

N(1)—Cu(1)—N(3)	95.56 (12)	N(5)—Cu(2)—N(7)	93.66 (12)
N(1)—Cu(1)—N(9)	121.37 (12)	N(5)—Cu(2)—N(11)	115.27 (11)
N(3)—Cu(1)—N(9)	142.95 (12)	N(7)—Cu(2)—N(11)	150.78 (12)

Acknowledgements

We gratefully acknowledge support of this work by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture.

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