Di-μ-iodido-bis­[(dimethyl 2,2′-biquinoline-4,4′-dicarboxyl­ate-κ2N,N′)copper(I)]

Starosta, R.; Komarnicka, U.K.; Nagaj, J.; Stokowa-Sołtys, K.; Bykowska, A.

doi:10.1107/S1600536812020843

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m756-m757

doi:10.1107/S1600536812020843

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Di-μ-iodido-bis[(dimethyl 2,2′-biquinoline-4,4′-dicarboxylate-κ²N,N′)copper(I)]

Radosław Starosta,^a ^* Urszula K. Komarnicka,^a Justyna Nagaj,^a Kamila Stokowa-Sołtys ^a and Aleksandra Bykowska ^a

^aFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
^*Correspondence e-mail: radoslaw.starosta@chem.uni.wroc.pl

(Received 12 April 2012; accepted 8 May 2012; online 12 May 2012)

In the centrosymmetric dinuclear title complex, [Cu₂I₂(C₂₂H₁₆N₂O₄)₂], the Cu^I atom is coordinated in a distorted tetrahedral geometry by an N,N′-bidentate dimethyl 2,2′-biquinoline-4,4′-dicarboxylate ligand and two symmetry-related I atoms, which act as bridges to a symmetry-related Cu^I atom. The distance between the Cu^I atoms within the dinuclear unit is 2.6723 (11) Å.

Related literature

Copper(I) complexes are a subject of high interest and have been extensively studied during the past two decades because of their diversified photo-physical properties (Lavie-Cambot et al., 2008 ; Vorontsov et al., 2009 ; Hashimoto et al., 2011 ). The title complex is similar to other copper(I) complexes with halides and aromatic diimines: [Cu₂I₂(1,10-phenanthroline)₂] and Cu₂X₂(2,9-dimethyl-1,10-phenanthroline)₂], where X = I, Br, Cl (Healy et al., 1985 ); [Cu₂X₂(1,10-phenanthroline)₂], where X = Cl and I (Yu et al., 2004 ); [Cu₂X₂(NN)₂], where X = Br, I and NN = bidentate imino nitroxides (Oshio et al., 1996 ); [Cu₂Cl₂(dihexsyl-2,2′-biquinoline-4,4′-dicarboxylate)₂] [Cu₂Cl₂(2,2′-biquinoline-4,4′-dicarboxylic acid)₂] (Vatsadze et al., 2010 ). For the preparation of the dimethyl-2,2′-biquinoline-4,4′-dicarboxylate ligand, see: Pucci et al. (2011 ) and of the P(CH₂N(CH₂CH₂)₂O)₃ phosphane ligand, see: Starosta et al. (2010 ).

Experimental

Crystal data

[Cu₂I₂(C₂₂H₁₆N₂O₄)₂]
M_r = 1125.62
Triclinic, $[P \overline 1]$
a = 8.792 (3) Å
b = 9.157 (3) Å
c = 12.865 (4) Å
α = 96.59 (3)°
β = 102.49 (3)°
γ = 103.51 (3)°
V = 968.2 (5) Å³
Z = 1
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.10 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.466, T_max = 0.912
15308 measured reflections
5471 independent reflections
4606 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.02
5471 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −1.16 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1A	2.088 (2)
Cu1—N1B	2.092 (2)
Cu1—I1	2.5473 (10)
Cu1—I1ⁱ	2.6996 (9)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020843/kp2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020843/kp2406Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the studied bis((µ-iodo)-(dimethyl-2,2'-biquinoline-4,4'-dicarboxylate))-di-copper(I) complex consist of the [(dimethyl-2,2'-biquinoline-4,4'-dicarboxylate)Cu(I)] moiety (Fig. 1, Table 1). Cu^I atoms are bridged by two iodide ions forming the planar rhombic Cu₂(µ-I)₂ core. Additionally coordinated by the imine nitrogen atoms of the dimethyl-2,2'-biquinoline-4,4'-dicarboxylate ligand, each Cu^I atom reveals a distorted tetrahedral geometry. Connected quinoline rings of the coordinated molecule of dimethyl-2,2'-biquinoline-4,4'-dicarboxylate are not coplanar, the angle between their planes is 5.40 (7)°.

Related literature top

Copper(I) complexes are a subject of high interest and have been extensively studied during past two decades because of their diversified photo-physical properties (Lavie-Cambot et al., 2008; Vorontsov et al., 2009; Hashimoto et al., 2011). The title complex is similar to other copper(I) complexes with halides and aromatic diimines: [Cu₂I₂(1,10-phenanthroline)₂] and Cu₂X₂(2,9-dimethyl-1,10-phenanthroline)₂], where X = I, Br, Cl (Healy et al., 1985); [Cu₂X₂(1,10-phenanthroline)₂], where X = Cl and I (Yu et al., 2004); [Cu₂X₂(NN)₂], where X = Br, I and NN = bidentate imino nitroxides (Oshio et al., 1996); [Cu₂Cl₂(diheksyl-2,2'-biquinoline-4,4'-dicarboxylate)₂] [Cu₂Cl₂(2,2'-biquinoline-4,4'-dicarboxylic acid)₂] (Vatsadze et al., 2010). For the preparation of the dimethyl-2,2'-biquinoline-4,4'-dicarboxylate ligand, see: Pucci et al. (2011)and of the P(CH₂N(CH₂CH₂)₂O)₃ phosphane ligand, see: Starosta et al.. (2010).

Experimental top

Crystals of the title complex were grown in the mixture of dichloromethane and acetone in an attempt to obtain crystals of [Cu(I)(dimethyl-2,2'-biquinoline-4,4'-dicarboxylate) P(CH₂N(CH₂CH₂)₂O)₃] complex. Cu^I was purchased from Aldrich. Dimethyl-2,2'-biquinoline-4,4'- dicarboxylate ligand was prepared from 2,2'-biquinoline-4,4'-dicarboxylic acid (Aldrich) according to the literature method (Pucci et al., 2011). P(CH₂N(CH₂CH₂)₂O)₃ phosphane ligand was synthesized as described previously (Starosta et al., 2010).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the complex showing the atom-labelling scheme and displacement ellipsoids at the 50% probability (symmmetry code used: -x + 1, -y, -z + 1).

Di-µ-iodido-bis[(dimethyl 2,2'-biquinoline-4,4'-dicarboxylate- κ²N,N')copper(I)] top

Crystal data top

[Cu₂I₂(C₂₂H₁₆N₂O₄)₂]	Z = 1
M_r = 1125.62	F(000) = 552
Triclinic, P1	D_x = 1.930 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.792 (3) Å	Cell parameters from 11359 reflections
b = 9.157 (3) Å	θ = 2.9–36.8°
c = 12.865 (4) Å	µ = 2.76 mm⁻¹
α = 96.59 (3)°	T = 100 K
β = 102.49 (3)°	Plate, orange
γ = 103.51 (3)°	0.15 × 0.10 × 0.10 mm
V = 968.2 (5) Å³

Data collection top

Kuma KM-4-CCD κ-geometry diffractometer	5471 independent reflections
Radiation source: fine-focus sealed tube	4606 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 30.0°, θ_min = 2.9°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), based on expressions derived by Clark & Reid (1995)]	h = −10→12
T_min = 0.466, T_max = 0.912	k = −12→11
15308 measured reflections	l = −17→17

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
5471 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −1.16 e Å⁻³

Crystal data top

[Cu₂I₂(C₂₂H₁₆N₂O₄)₂]	γ = 103.51 (3)°
M_r = 1125.62	V = 968.2 (5) Å³
Triclinic, P1	Z = 1
a = 8.792 (3) Å	Mo Kα radiation
b = 9.157 (3) Å	µ = 2.76 mm⁻¹
c = 12.865 (4) Å	T = 100 K
α = 96.59 (3)°	0.15 × 0.10 × 0.10 mm
β = 102.49 (3)°

Data collection top

Kuma KM-4-CCD κ-geometry diffractometer	5471 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), based on expressions derived by Clark & Reid (1995)]	4606 reflections with I > 2σ(I)
T_min = 0.466, T_max = 0.912	R_int = 0.028
15308 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	Δρ_max = 0.89 e Å⁻³
5471 reflections	Δρ_min = −1.16 e Å⁻³
273 parameters

Special details top

Experimental. Absorption correction: CrysAlis RED, (Oxford Diffraction, 2006). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S., 1995)

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
Cu1	0.34262 (3)	−0.02511 (3)	0.49564 (2)	0.01649 (7)
I1	0.495174 (17)	0.240323 (17)	0.478225 (12)	0.01826 (5)
N1A	0.1380 (2)	−0.1629 (2)	0.38141 (15)	0.0142 (3)
C2A	0.0293 (3)	−0.2436 (3)	0.42433 (18)	0.0153 (4)
C3A	−0.0976 (3)	−0.3688 (3)	0.36264 (18)	0.0172 (4)
H3A	−0.1715	−0.4265	0.3963	0.021*
C4A	−0.1132 (3)	−0.4064 (3)	0.25341 (18)	0.0165 (4)
C5A	−0.0028 (3)	−0.3491 (3)	0.09277 (18)	0.0191 (4)
H5A	−0.0859	−0.4295	0.0451	0.023*
C6A	0.1133 (3)	−0.2621 (3)	0.05366 (19)	0.0204 (5)
H6A	0.1111	−0.2840	−0.0207	0.024*
C7A	0.2367 (3)	−0.1399 (3)	0.12198 (19)	0.0200 (5)
H7A	0.3155	−0.0795	0.0932	0.024*
C8A	0.2426 (3)	−0.1086 (3)	0.22991 (19)	0.0178 (4)
H8A	0.3256	−0.0265	0.2759	0.021*
C9A	0.1252 (3)	−0.1986 (2)	0.27237 (18)	0.0150 (4)
C10A	−0.0005 (3)	−0.3205 (3)	0.20414 (18)	0.0158 (4)
C11A	−0.2508 (3)	−0.5363 (3)	0.18690 (19)	0.0190 (4)
O11A	−0.3182 (2)	−0.5417 (2)	0.09388 (14)	0.0281 (4)
O12A	−0.28999 (19)	−0.64555 (19)	0.24393 (14)	0.0212 (3)
C12A	−0.4228 (3)	−0.7757 (3)	0.1849 (2)	0.0245 (5)
H12D	−0.5155	−0.7399	0.1519	0.037*
H12E	−0.4536	−0.8435	0.2349	0.037*
H12F	−0.3887	−0.8313	0.1283	0.037*
N1B	0.1763 (2)	−0.0732 (2)	0.58953 (15)	0.0144 (3)
C2B	0.0491 (2)	−0.1915 (3)	0.54192 (17)	0.0140 (4)
C3B	−0.0588 (3)	−0.2629 (3)	0.59879 (18)	0.0154 (4)
H3B	−0.1447	−0.3501	0.5632	0.019*
C4B	−0.0395 (3)	−0.2061 (3)	0.70607 (18)	0.0155 (4)
C5B	0.1212 (3)	−0.0045 (3)	0.86815 (18)	0.0169 (4)
H5B	0.0512	−0.0429	0.9113	0.020*
C6B	0.2517 (3)	0.1184 (3)	0.91204 (18)	0.0193 (4)
H6B	0.2709	0.1642	0.9854	0.023*
C7B	0.3583 (3)	0.1782 (3)	0.85011 (19)	0.0188 (4)
H7B	0.4489	0.2630	0.8821	0.023*
C8B	0.3309 (3)	0.1139 (3)	0.74412 (18)	0.0176 (4)
H8B	0.4023	0.1548	0.7025	0.021*
C9B	0.1967 (3)	−0.0135 (3)	0.69604 (18)	0.0153 (4)
C10B	0.0894 (3)	−0.0752 (2)	0.75828 (17)	0.0145 (4)
C11B	−0.1583 (3)	−0.2831 (3)	0.76375 (18)	0.0163 (4)
O11B	−0.1970 (2)	−0.2197 (2)	0.83756 (14)	0.0220 (4)
O12B	−0.2166 (2)	−0.43175 (19)	0.72286 (14)	0.0210 (3)
C12B	−0.3430 (3)	−0.5141 (3)	0.7667 (2)	0.0241 (5)
H12A	−0.3126	−0.4851	0.8456	0.036*
H12B	−0.3575	−0.6240	0.7470	0.036*
H12C	−0.4443	−0.4890	0.7371	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01350 (13)	0.01802 (14)	0.01445 (13)	−0.00091 (10)	0.00308 (10)	0.00031 (10)
I1	0.01682 (7)	0.01604 (7)	0.01965 (8)	0.00169 (5)	0.00320 (5)	0.00222 (5)
N1A	0.0140 (8)	0.0151 (9)	0.0116 (8)	0.0030 (7)	0.0011 (7)	0.0007 (7)
C2A	0.0139 (9)	0.0167 (10)	0.0136 (10)	0.0032 (8)	0.0028 (8)	−0.0001 (8)
C3A	0.0139 (10)	0.0188 (11)	0.0161 (10)	0.0003 (8)	0.0029 (8)	0.0020 (8)
C4A	0.0170 (10)	0.0145 (10)	0.0150 (10)	0.0019 (8)	0.0020 (8)	−0.0011 (8)
C5A	0.0216 (11)	0.0190 (11)	0.0140 (10)	0.0038 (9)	0.0028 (8)	−0.0011 (8)
C6A	0.0274 (12)	0.0200 (11)	0.0122 (10)	0.0059 (9)	0.0039 (9)	−0.0006 (8)
C7A	0.0227 (11)	0.0205 (11)	0.0170 (10)	0.0040 (9)	0.0063 (9)	0.0051 (9)
C8A	0.0173 (10)	0.0180 (11)	0.0160 (10)	0.0026 (8)	0.0023 (8)	0.0027 (8)
C9A	0.0145 (9)	0.0146 (10)	0.0142 (10)	0.0028 (8)	0.0018 (8)	0.0016 (8)
C10A	0.0150 (10)	0.0160 (10)	0.0140 (10)	0.0031 (8)	0.0009 (8)	−0.0001 (8)
C11A	0.0157 (10)	0.0198 (11)	0.0186 (11)	0.0011 (8)	0.0053 (8)	−0.0024 (9)
O11A	0.0260 (9)	0.0315 (10)	0.0161 (8)	−0.0037 (8)	−0.0016 (7)	−0.0013 (7)
O12A	0.0164 (8)	0.0178 (8)	0.0224 (8)	−0.0030 (6)	0.0000 (6)	0.0000 (7)
C12A	0.0162 (11)	0.0184 (11)	0.0312 (13)	−0.0030 (9)	0.0012 (10)	−0.0017 (10)
N1B	0.0129 (8)	0.0160 (9)	0.0123 (8)	0.0013 (7)	0.0024 (7)	0.0008 (7)
C2B	0.0121 (9)	0.0148 (10)	0.0124 (9)	0.0012 (7)	0.0013 (7)	0.0002 (8)
C3B	0.0118 (9)	0.0170 (10)	0.0151 (10)	0.0016 (8)	0.0012 (8)	0.0016 (8)
C4B	0.0129 (9)	0.0173 (10)	0.0158 (10)	0.0034 (8)	0.0039 (8)	0.0021 (8)
C5B	0.0176 (10)	0.0192 (11)	0.0138 (10)	0.0056 (8)	0.0036 (8)	0.0022 (8)
C6B	0.0220 (11)	0.0211 (11)	0.0124 (10)	0.0053 (9)	0.0024 (8)	−0.0020 (8)
C7B	0.0175 (10)	0.0162 (10)	0.0180 (10)	0.0004 (8)	0.0018 (8)	−0.0021 (8)
C8B	0.0167 (10)	0.0181 (11)	0.0157 (10)	0.0007 (8)	0.0047 (8)	0.0005 (8)
C9B	0.0141 (9)	0.0168 (10)	0.0142 (10)	0.0042 (8)	0.0023 (8)	0.0011 (8)
C10B	0.0142 (9)	0.0157 (10)	0.0135 (10)	0.0042 (8)	0.0030 (8)	0.0021 (8)
C11B	0.0145 (9)	0.0182 (10)	0.0149 (10)	0.0035 (8)	0.0017 (8)	0.0036 (8)
O11B	0.0212 (8)	0.0233 (9)	0.0191 (8)	0.0007 (7)	0.0085 (7)	−0.0016 (7)
O12B	0.0214 (8)	0.0167 (8)	0.0250 (9)	0.0013 (6)	0.0110 (7)	0.0025 (7)
C12B	0.0244 (12)	0.0179 (11)	0.0299 (13)	0.0001 (9)	0.0132 (10)	0.0042 (10)

Geometric parameters (Å, º) top

Cu1—N1A	2.088 (2)	C12A—H12D	0.9800
Cu1—N1B	2.092 (2)	C12A—H12E	0.9800
Cu1—I1	2.5473 (10)	C12A—H12F	0.9800
Cu1—I1ⁱ	2.6996 (9)	N1B—C2B	1.336 (3)
Cu1—Cu1ⁱ	2.6723 (11)	N1B—C9B	1.373 (3)
I1—Cu1ⁱ	2.6997 (9)	C2B—C3B	1.408 (3)
N1A—C2A	1.325 (3)	C3B—C4B	1.377 (3)
N1A—C9A	1.377 (3)	C3B—H3B	0.9500
C2A—C3A	1.414 (3)	C4B—C10B	1.422 (3)
C2A—C2B	1.493 (3)	C4B—C11B	1.500 (3)
C3A—C4A	1.377 (3)	C5B—C6B	1.368 (3)
C3A—H3A	0.9500	C5B—C10B	1.425 (3)
C4A—C10A	1.423 (3)	C5B—H5B	0.9500
C4A—C11A	1.502 (3)	C6B—C7B	1.413 (3)
C5A—C6A	1.366 (3)	C6B—H6B	0.9500
C5A—C10A	1.421 (3)	C7B—C8B	1.368 (3)
C5A—H5A	0.9500	C7B—H7B	0.9500
C6A—C7A	1.412 (3)	C8B—C9B	1.419 (3)
C6A—H6A	0.9500	C8B—H8B	0.9500
C7A—C8A	1.372 (3)	C9B—C10B	1.426 (3)
C7A—H7A	0.9500	C11B—O11B	1.208 (3)
C8A—C9A	1.412 (3)	C11B—O12B	1.336 (3)
C8A—H8A	0.9500	O12B—C12B	1.448 (3)
C9A—C10A	1.420 (3)	C12B—H12A	0.9800
C11A—O11A	1.205 (3)	C12B—H12B	0.9800
C11A—O12A	1.332 (3)	C12B—H12C	0.9800
O12A—C12A	1.455 (3)

N1A—Cu1—N1B	78.10 (8)	O12A—C12A—H12F	109.5
N1A—Cu1—I1	124.55 (6)	H12D—C12A—H12F	109.5
N1B—Cu1—I1	125.61 (6)	H12E—C12A—H12F	109.5
N1A—Cu1—I1ⁱ	96.95 (6)	C2B—N1B—C9B	118.65 (19)
N1B—Cu1—I1ⁱ	103.46 (6)	C2B—N1B—Cu1	113.28 (14)
I1—Cu1—I1ⁱ	118.85 (3)	C9B—N1B—Cu1	127.25 (15)
Cu1—I1—Cu1ⁱ	61.15 (3)	N1B—C2B—C3B	122.3 (2)
C2A—N1A—C9A	119.28 (19)	N1B—C2B—C2A	115.52 (19)
C2A—N1A—Cu1	113.75 (15)	C3B—C2B—C2A	122.14 (19)
C9A—N1A—Cu1	125.41 (15)	C4B—C3B—C2B	119.9 (2)
N1A—C2A—C3A	122.3 (2)	C4B—C3B—H3B	120.1
N1A—C2A—C2B	115.21 (19)	C2B—C3B—H3B	120.1
C3A—C2A—C2B	122.5 (2)	C3B—C4B—C10B	119.5 (2)
C4A—C3A—C2A	119.4 (2)	C3B—C4B—C11B	118.5 (2)
C4A—C3A—H3A	120.3	C10B—C4B—C11B	121.9 (2)
C2A—C3A—H3A	120.3	C6B—C5B—C10B	120.6 (2)
C3A—C4A—C10A	119.8 (2)	C6B—C5B—H5B	119.7
C3A—C4A—C11A	119.7 (2)	C10B—C5B—H5B	119.7
C10A—C4A—C11A	120.5 (2)	C5B—C6B—C7B	121.1 (2)
C6A—C5A—C10A	120.6 (2)	C5B—C6B—H6B	119.4
C6A—C5A—H5A	119.7	C7B—C6B—H6B	119.4
C10A—C5A—H5A	119.7	C8B—C7B—C6B	119.9 (2)
C5A—C6A—C7A	121.1 (2)	C8B—C7B—H7B	120.0
C5A—C6A—H6A	119.5	C6B—C7B—H7B	120.0
C7A—C6A—H6A	119.5	C7B—C8B—C9B	120.4 (2)
C8A—C7A—C6A	120.0 (2)	C7B—C8B—H8B	119.8
C8A—C7A—H7A	120.0	C9B—C8B—H8B	119.8
C6A—C7A—H7A	120.0	N1B—C9B—C8B	117.5 (2)
C7A—C8A—C9A	119.8 (2)	N1B—C9B—C10B	122.5 (2)
C7A—C8A—H8A	120.1	C8B—C9B—C10B	120.0 (2)
C9A—C8A—H8A	120.1	C4B—C10B—C5B	125.0 (2)
N1A—C9A—C8A	117.3 (2)	C4B—C10B—C9B	117.0 (2)
N1A—C9A—C10A	122.1 (2)	C5B—C10B—C9B	118.0 (2)
C8A—C9A—C10A	120.6 (2)	O11B—C11B—O12B	124.0 (2)
C9A—C10A—C5A	117.9 (2)	O11B—C11B—C4B	124.8 (2)
C9A—C10A—C4A	117.1 (2)	O12B—C11B—C4B	111.19 (19)
C5A—C10A—C4A	125.0 (2)	C11B—O12B—C12B	115.55 (18)
O11A—C11A—O12A	123.9 (2)	O12B—C12B—H12A	109.5
O11A—C11A—C4A	124.7 (2)	O12B—C12B—H12B	109.5
O12A—C11A—C4A	111.4 (2)	H12A—C12B—H12B	109.5
C11A—O12A—C12A	114.73 (19)	O12B—C12B—H12C	109.5
O12A—C12A—H12D	109.5	H12A—C12B—H12C	109.5
O12A—C12A—H12E	109.5	H12B—C12B—H12C	109.5
H12D—C12A—H12E	109.5

N1A—Cu1—I1—Cu1ⁱ	−123.16 (7)	I1—Cu1—N1B—C2B	140.88 (14)
N1B—Cu1—I1—Cu1ⁱ	136.17 (7)	I1ⁱ—Cu1—N1B—C2B	−77.71 (15)
I1ⁱ—Cu1—I1—Cu1ⁱ	0.0	N1A—Cu1—N1B—C9B	−173.9 (2)
N1B—Cu1—N1A—C2A	−17.89 (15)	I1—Cu1—N1B—C9B	−49.7 (2)
I1—Cu1—N1A—C2A	−143.16 (14)	I1ⁱ—Cu1—N1B—C9B	91.69 (18)
I1ⁱ—Cu1—N1A—C2A	84.46 (15)	C9B—N1B—C2B—C3B	−4.1 (3)
N1B—Cu1—N1A—C9A	176.59 (19)	Cu1—N1B—C2B—C3B	166.34 (17)
I1—Cu1—N1A—C9A	51.33 (19)	C9B—N1B—C2B—C2A	176.24 (19)
I1ⁱ—Cu1—N1A—C9A	−81.05 (18)	Cu1—N1B—C2B—C2A	−13.4 (2)
C9A—N1A—C2A—C3A	1.9 (3)	N1A—C2A—C2B—N1B	−1.9 (3)
Cu1—N1A—C2A—C3A	−164.62 (17)	C3A—C2A—C2B—N1B	179.0 (2)
C9A—N1A—C2A—C2B	−177.27 (19)	N1A—C2A—C2B—C3B	178.4 (2)
Cu1—N1A—C2A—C2B	16.2 (2)	C3A—C2A—C2B—C3B	−0.7 (3)
N1A—C2A—C3A—C4A	−2.1 (3)	N1B—C2B—C3B—C4B	3.3 (3)
C2B—C2A—C3A—C4A	177.0 (2)	C2A—C2B—C3B—C4B	−177.0 (2)
C2A—C3A—C4A—C10A	0.9 (3)	C2B—C3B—C4B—C10B	0.2 (3)
C2A—C3A—C4A—C11A	−178.1 (2)	C2B—C3B—C4B—C11B	178.9 (2)
C10A—C5A—C6A—C7A	−1.2 (4)	C10B—C5B—C6B—C7B	−0.1 (4)
C5A—C6A—C7A—C8A	1.0 (4)	C5B—C6B—C7B—C8B	0.6 (4)
C6A—C7A—C8A—C9A	0.0 (3)	C6B—C7B—C8B—C9B	−0.5 (4)
C2A—N1A—C9A—C8A	179.3 (2)	C2B—N1B—C9B—C8B	−178.8 (2)
Cu1—N1A—C9A—C8A	−15.9 (3)	Cu1—N1B—C9B—C8B	12.3 (3)
C2A—N1A—C9A—C10A	−0.5 (3)	C2B—N1B—C9B—C10B	1.5 (3)
Cu1—N1A—C9A—C10A	164.31 (16)	Cu1—N1B—C9B—C10B	−167.44 (16)
C7A—C8A—C9A—N1A	179.4 (2)	C7B—C8B—C9B—N1B	−179.7 (2)
C7A—C8A—C9A—C10A	−0.8 (3)	C7B—C8B—C9B—C10B	0.0 (3)
N1A—C9A—C10A—C5A	−179.6 (2)	C3B—C4B—C10B—C5B	179.2 (2)
C8A—C9A—C10A—C5A	0.6 (3)	C11B—C4B—C10B—C5B	0.6 (3)
N1A—C9A—C10A—C4A	−0.6 (3)	C3B—C4B—C10B—C9B	−2.6 (3)
C8A—C9A—C10A—C4A	179.5 (2)	C11B—C4B—C10B—C9B	178.8 (2)
C6A—C5A—C10A—C9A	0.4 (3)	C6B—C5B—C10B—C4B	177.8 (2)
C6A—C5A—C10A—C4A	−178.5 (2)	C6B—C5B—C10B—C9B	−0.4 (3)
C3A—C4A—C10A—C9A	0.4 (3)	N1B—C9B—C10B—C4B	1.8 (3)
C11A—C4A—C10A—C9A	179.4 (2)	C8B—C9B—C10B—C4B	−177.9 (2)
C3A—C4A—C10A—C5A	179.3 (2)	N1B—C9B—C10B—C5B	−179.8 (2)
C11A—C4A—C10A—C5A	−1.7 (3)	C8B—C9B—C10B—C5B	0.4 (3)
C3A—C4A—C11A—O11A	146.9 (3)	C3B—C4B—C11B—O11B	−149.8 (2)
C10A—C4A—C11A—O11A	−32.1 (4)	C10B—C4B—C11B—O11B	28.8 (3)
C3A—C4A—C11A—O12A	−32.9 (3)	C3B—C4B—C11B—O12B	30.2 (3)
C10A—C4A—C11A—O12A	148.1 (2)	C10B—C4B—C11B—O12B	−151.2 (2)
O11A—C11A—O12A—C12A	0.2 (3)	O11B—C11B—O12B—C12B	5.1 (3)
C4A—C11A—O12A—C12A	179.96 (18)	C4B—C11B—O12B—C12B	−174.87 (19)
N1A—Cu1—N1B—C2B	16.69 (15)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂I₂(C₂₂H₁₆N₂O₄)₂]
M_r	1125.62
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.792 (3), 9.157 (3), 12.865 (4)
α, β, γ (°)	96.59 (3), 102.49 (3), 103.51 (3)
V (Å³)	968.2 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Kuma KM-4-CCD κ-geometry diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2006), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.466, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	15308, 5471, 4606
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.02
No. of reflections	5471
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −1.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—N1A	2.088 (2)	Cu1—I1ⁱ	2.6996 (9)
Cu1—N1B	2.092 (2)	Cu1—Cu1ⁱ	2.6723 (11)
Cu1—I1	2.5473 (10)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors are grateful to Dr Miłosz Siczek for the crystal measurements and help with the preparation of this manuscript.

References

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