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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1286–m1287.
Published online 2009 October 3. doi:  10.1107/S1600536809039622
PMCID: PMC2971412

{μ-Bis(1-methyl­imidazol-2-yl)methane-κ2 N 3:N 3′}bis­{[(1-methyl­imidazol-2-yl)methane-κ2 N 3,N 3′]copper(I)} bis­(tri­fluoro­methane­sulfonate)

Abstract

The title compound, [Cu2(C9H12N4)3](CF3SO3)2, contains two CuI ions, three bis­(1-methyl­imidazol-2-yl)methane (Me2BIM) ligands, and two trifluoromethanesulfonate anions in the asymmetric unit. Each CuI 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 CuI 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 [triangle]). For coordination complexes with one or two Me2BIM ligands chelating one metal center, see: Elgafi et al. (1999 [triangle]); Abuskhuna et al. (2004a [triangle]); Burling et al. (2004 [triangle]); Kennedy et al. (2007 [triangle]); Dabb et al. (2009 [triangle]). For CuII complexes with two BIM ligands chelating one metal center, see: Place et al. (1998 [triangle]). For AgI complexes with two BIM ligands bridging two metals, see: Abuskhuna et al. (2004b [triangle]). The Me2BIM ligand was synthesized by modified literature methods (Byers & Canty, 1990 [triangle]; Elgafi et al., 1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1286-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C9H12N4)3](CF3SO3)2
  • M r = 953.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1286-efi1.jpg
  • 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 I 2 > 2σ(I 2)
  • R int = 0.039

Refinement

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

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039622/bv2129Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

Ligand bis(imidazol-2-yl)methane derivative is a bidentate ligand, either chelating one metal center or bridging two metals. The crystal structures of CuII 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 AgI complex with BIM has been reported by Abuskhuna et al. (2004b). The CuII complexes have four- or six-coordinate structure that is coordinated with two Me2BIM ligands, and the AgI complex forms a two-coordinate structure bridged by BIM. The title compound, [(µ-Me2BIM){Cu(Me2BIM)}2](OTf)2, contains two CuI ions, three bis(1-methylimidazol-2-yl)methane (Me2BIM) ligands, and two trifluoromethanesulfonate anions as an independent unit in the unit cell. Each CuI 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 CuI ion. This is a novel dinuclear CuI 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.

Experimental

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.

Refinement

Hydrogen atoms attached to carbon atoms were positioned geometrically and treated as riding with aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å, and methylenic C—H = 0.99 Å and with Uiso(H) = 1.2Ueq(C).

Figures

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 ...

Crystal data

[Cu2(C9H12N4)3](CF3SO3)2F(000) = 1944.00
Mr = 953.88Dx = 1.658 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 10516 reflections
a = 22.5575 (11) Åθ = 3.0–27.5°
b = 7.0307 (3) ŵ = 1.31 mm1
c = 25.4982 (16) ÅT = 173 K
β = 109.118 (2)°Block, yellow
V = 3820.9 (3) Å30.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Rigaku Mercury diffractometerRint = 0.039
Detector resolution: 7.31 pixels mm-1θmax = 27.5°
ω scansh = −29→23
29376 measured reflectionsk = −9→9
8745 independent reflectionsl = −27→33
6639 reflections with F2 > 2σ(F2)

Refinement

Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.055All H-atom parameters refined
wR(F2) = 0.146w = 1/[σ2(Fo2) + (0.0583P)2 + 1.5952P] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
8745 reflectionsΔρmax = 0.58 e Å3
515 parametersΔρmin = −0.72 e Å3

Special details

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)

xyzUiso*/Ueq
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)0.66290.22031.01520.065*
H(3B)0.70320.27450.97610.065*
H(3C)0.68770.05640.98410.065*
H(9A)0.7932−0.05780.80480.079*
H(9B)0.7597−0.16980.84200.079*
H(9C)0.78030.04740.85570.079*
H(12A)0.28140.96700.74000.080*
H(12B)0.34241.03330.78940.080*
H(12C)0.31900.81740.78630.080*
H(18A)0.56870.72570.96300.074*
H(18B)0.49800.68110.92540.074*
H(18C)0.52540.89190.92750.074*
H(21A)0.30130.50460.58180.063*
H(21B)0.28910.28000.57720.063*
H(21C)0.34660.36880.56190.063*
H(27A)0.52620.23180.50330.073*
H(27B)0.46140.20020.51510.073*
H(27C)0.52260.08320.54970.073*
H(5A)0.6759−0.02320.88210.049*
H(5B)0.69710.19230.88070.049*
H(14A)0.43080.69400.82470.051*
H(14B)0.45500.90840.82890.051*
H(23A)0.42790.19250.59020.050*
H(23B)0.48200.11550.64360.050*
H(1)0.47470.29600.87140.050*
H(2)0.54700.29730.96800.053*
H(7)0.59980.10310.67710.060*
H(8)0.7077−0.02160.70930.064*
H(10)0.39500.81570.62340.061*
H(11)0.30560.93030.64910.063*
H(16)0.64820.56500.82260.065*
H(17)0.64940.62400.91780.068*
H(19)0.39460.35970.77220.045*
H(20)0.30340.43370.68930.049*
H(25)0.59390.71000.63640.060*
H(26)0.59040.52070.55410.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2129).

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