Di-μ-iodo-bis{[bis(trans-cinnam­aldehyde)­ethyl­enedi­imine-κ²N,N′]copper(I)}

The title complex, [Cu(μ-I)(ca₂en)]₂ [ca₂en is N,N′-bis(trans-cinnam­aldehyde)­ethyl­enedi­imine, C₂₀H₂₀N₂], has a dimeric structure where two copper(I) ions are doubly bridged by iodine substituents. The inversion center is located midway between the two Cu atoms. The ca₂en acts as a bidentate ligand coordinating via two N atoms to the copper. The coordination geometry around the Cu atom is a distorted tetrahedron formed by two N atoms from a bidentate di­imine ligand and two iodine substituents. The distance between the two Cu atoms is 2.635 (2) Å. The ca₂en ligand adopts a Z,Z configuration.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.068
• wR factor = 0.158
• Data-to-parameter ratio = 18.2

checkCIF results

No syntax errors found

Structure: I
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ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Cu2I2(C20H20N2)2]	F(000) = 1888
Mr = 957.64	Dx = 1.647 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.031 (3) Å	Cell parameters from 3249 reflections
b = 11.926 (3) Å	θ = 3.0–24.4°
c = 27.060 (7) Å	µ = 2.73 mm^−1
β = 95.877 (4)°	T = 294 K
V = 3862.2 (16) Å^3	Plate, orange
Z = 4	0.20 × 0.20 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3953 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω' scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.611, Tmax = 0.923	k = −14→14
11236 measured reflections	l = −33→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 62.8396P] where P = (Fo^2 + 2Fc^2)/3
3953 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 1.72 e Å^−3
0 restraints	Δρmin = −1.01 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.13653 (5)	0.03525 (5)	0.54957 (3)	0.0511 (2)
Cu1	0.01233 (10)	0.10648 (8)	0.48879 (4)	0.0454 (3)
C1	−0.1429 (9)	−0.0183 (9)	0.2854 (4)	0.063 (3)
H1A	−0.1338	−0.0463	0.3177	0.076*
C2	−0.1484 (10)	−0.0911 (10)	0.2460 (5)	0.073 (3)
H2A	−0.1447	−0.1679	0.2519	0.088*
C3	−0.1596 (9)	−0.0521 (11)	0.1978 (4)	0.069 (3)
H3A	−0.1606	−0.1017	0.1712	0.083*
C4	−0.1692 (10)	0.0622 (10)	0.1896 (4)	0.070 (3)
H4A	−0.1785	0.0901	0.1574	0.084*
C5	−0.1649 (9)	0.1339 (10)	0.2291 (4)	0.063 (3)
H5A	−0.1719	0.2104	0.2230	0.076*
C6	−0.1507 (8)	0.0976 (9)	0.2777 (4)	0.051 (2)
C7	−0.1440 (8)	0.1774 (9)	0.3179 (4)	0.053 (2)
H7A	−0.1696	0.2493	0.3099	0.063*
C8	−0.1050 (8)	0.1596 (8)	0.3655 (3)	0.050 (2)
H8A	−0.0780	0.0890	0.3751	0.061*
C9	−0.1039 (7)	0.2483 (8)	0.4023 (4)	0.048 (2)
H9A	−0.1315	0.3185	0.3922	0.057*
N10	−0.0671 (6)	0.2346 (6)	0.4474 (3)	0.0446 (18)
C11	−0.0685 (8)	0.3305 (7)	0.4817 (4)	0.050 (2)
H11A	−0.1207	0.3161	0.5059	0.060*
H11B	−0.0928	0.3974	0.4632	0.060*
C12	0.0476 (8)	0.3487 (7)	0.5079 (4)	0.049 (2)
H12A	0.0961	0.3796	0.4848	0.058*
H12B	0.0443	0.4014	0.5350	0.058*
N13	0.0928 (7)	0.2397 (6)	0.5274 (3)	0.0441 (18)
C14	0.1719 (8)	0.2419 (8)	0.5622 (4)	0.048 (2)
H14A	0.1955	0.3105	0.5759	0.057*
C15	0.2257 (7)	0.1408 (7)	0.5809 (3)	0.044 (2)
H15A	0.1955	0.0727	0.5695	0.053*
C16	0.3159 (7)	0.1388 (8)	0.6134 (4)	0.049 (2)
H16A	0.3409	0.2076	0.6263	0.059*
C17	0.3807 (7)	0.0403 (9)	0.6314 (3)	0.048 (2)
C18	0.4634 (9)	0.0502 (11)	0.6704 (4)	0.072 (3)
H18A	0.4769	0.1192	0.6859	0.086*
C19	0.5261 (10)	−0.0421 (14)	0.6865 (5)	0.089 (4)
H19A	0.5810	−0.0351	0.7132	0.107*
C20	0.5083 (12)	−0.1449 (12)	0.6636 (5)	0.087 (4)
H20A	0.5515	−0.2064	0.6745	0.104*
C21	0.4270 (11)	−0.1563 (10)	0.6246 (5)	0.073 (3)
H21A	0.4140	−0.2256	0.6094	0.088*
C22	0.3649 (9)	−0.0645 (8)	0.6082 (4)	0.056 (3)
H22A	0.3111	−0.0721	0.5812	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0550 (4)	0.0385 (3)	0.0625 (4)	0.0060 (3)	0.0187 (3)	−0.0012 (3)
Cu1	0.0544 (7)	0.0237 (5)	0.0570 (7)	0.0049 (5)	0.0004 (5)	−0.0005 (5)
C1	0.074 (7)	0.064 (7)	0.050 (6)	−0.004 (6)	0.001 (5)	0.015 (6)
C2	0.092 (9)	0.055 (7)	0.071 (8)	−0.003 (6)	−0.001 (7)	0.002 (6)
C3	0.068 (7)	0.080 (9)	0.058 (7)	−0.003 (6)	−0.003 (6)	−0.008 (6)
C4	0.073 (8)	0.078 (9)	0.056 (7)	0.000 (6)	−0.003 (6)	0.005 (6)
C5	0.061 (7)	0.066 (7)	0.061 (7)	0.002 (6)	−0.005 (6)	0.009 (6)
C6	0.035 (5)	0.065 (7)	0.053 (6)	0.001 (5)	0.002 (4)	0.010 (5)
C7	0.055 (6)	0.049 (6)	0.053 (6)	0.005 (5)	0.000 (5)	0.002 (5)
C8	0.061 (6)	0.042 (5)	0.048 (6)	0.004 (5)	0.000 (5)	0.004 (4)
C9	0.046 (5)	0.039 (5)	0.058 (6)	0.012 (4)	0.001 (5)	0.011 (5)
N10	0.049 (4)	0.031 (4)	0.053 (5)	0.012 (3)	0.001 (4)	0.001 (3)
C11	0.054 (6)	0.025 (4)	0.072 (7)	0.016 (4)	0.009 (5)	0.000 (4)
C12	0.054 (6)	0.022 (4)	0.071 (7)	−0.003 (4)	0.015 (5)	−0.008 (4)
N13	0.059 (5)	0.027 (4)	0.047 (5)	0.005 (3)	0.011 (4)	−0.006 (3)
C14	0.047 (5)	0.040 (5)	0.056 (6)	−0.002 (4)	0.005 (5)	−0.013 (5)
C15	0.038 (5)	0.035 (5)	0.057 (6)	−0.001 (4)	0.001 (4)	−0.005 (4)
C16	0.038 (5)	0.048 (5)	0.061 (6)	−0.010 (4)	0.003 (5)	−0.015 (5)
C17	0.038 (5)	0.057 (6)	0.049 (5)	−0.001 (5)	0.006 (4)	−0.006 (5)
C18	0.051 (6)	0.091 (9)	0.073 (8)	0.002 (6)	0.000 (6)	−0.009 (7)
C19	0.058 (7)	0.135 (13)	0.071 (8)	0.029 (9)	−0.014 (6)	−0.002 (9)
C20	0.100 (11)	0.078 (9)	0.084 (10)	0.031 (8)	0.021 (8)	0.018 (8)
C21	0.084 (9)	0.058 (7)	0.081 (9)	0.020 (6)	0.019 (7)	0.011 (6)
C22	0.056 (6)	0.054 (6)	0.058 (6)	0.003 (5)	0.010 (5)	−0.003 (5)

Geometric parameters (Å, º)

I1—Cu1^i	2.5466 (13)	C11—C12	1.516 (13)
I1—Cu1	2.6903 (14)	C11—H11A	0.9700
Cu1—N10	2.069 (7)	C11—H11B	0.9700
Cu1—N13	2.085 (7)	C12—N13	1.485 (11)
Cu1—I1^i	2.5466 (13)	C12—H12A	0.9700
Cu1—Cu1^i	2.635 (2)	C12—H12B	0.9700
C1—C2	1.372 (15)	N13—C14	1.269 (11)
C1—C6	1.399 (14)	C14—C15	1.436 (12)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.379 (16)	C15—C16	1.325 (12)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.384 (16)	C16—C17	1.464 (13)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.365 (15)	C17—C18	1.381 (14)
C4—H4A	0.9300	C17—C22	1.402 (14)
C5—C6	1.378 (14)	C18—C19	1.380 (17)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.441 (14)	C19—C20	1.381 (19)
C7—C8	1.341 (13)	C19—H19A	0.9300
C7—H7A	0.9300	C20—C21	1.369 (17)
C8—C9	1.452 (13)	C20—H20A	0.9300
C8—H8A	0.9300	C21—C22	1.373 (14)
C9—N10	1.268 (11)	C21—H21A	0.9300
C9—H9A	0.9300	C22—H22A	0.9300
N10—C11	1.473 (11)
Cu1^i—I1—Cu1	60.35 (4)	N10—C11—H11A	109.7
N10—Cu1—N13	82.7 (3)	C12—C11—H11A	109.7
N10—Cu1—I1^i	121.8 (2)	N10—C11—H11B	109.7
N13—Cu1—I1^i	116.7 (2)	C12—C11—H11B	109.7
N10—Cu1—Cu1^i	141.2 (2)	H11A—C11—H11B	108.2
N13—Cu1—Cu1^i	132.6 (2)	N13—C12—C11	109.1 (7)
I1^i—Cu1—Cu1^i	62.53 (5)	N13—C12—H12A	109.9
N10—Cu1—I1	105.3 (2)	C11—C12—H12A	109.9
N13—Cu1—I1	103.8 (2)	N13—C12—H12B	109.9
I1^i—Cu1—I1	119.65 (4)	C11—C12—H12B	109.9
Cu1^i—Cu1—I1	57.12 (5)	H12A—C12—H12B	108.3
C2—C1—C6	120.8 (10)	C14—N13—C12	117.7 (8)
C2—C1—H1A	119.6	C14—N13—Cu1	131.5 (6)
C6—C1—H1A	119.6	C12—N13—Cu1	110.7 (6)
C1—C2—C3	121.0 (11)	N13—C14—C15	121.3 (8)
C1—C2—H2A	119.5	N13—C14—H14A	119.3
C3—C2—H2A	119.5	C15—C14—H14A	119.3
C2—C3—C4	118.8 (12)	C16—C15—C14	123.9 (9)
C2—C3—H3A	120.6	C16—C15—H15A	118.0
C4—C3—H3A	120.6	C14—C15—H15A	118.0
C5—C4—C3	119.8 (11)	C15—C16—C17	127.4 (9)
C5—C4—H4A	120.1	C15—C16—H16A	116.3
C3—C4—H4A	120.1	C17—C16—H16A	116.3
C4—C5—C6	122.7 (11)	C18—C17—C22	118.2 (10)
C4—C5—H5A	118.6	C18—C17—C16	120.2 (10)
C6—C5—H5A	118.6	C22—C17—C16	121.6 (8)
C5—C6—C1	116.9 (10)	C19—C18—C17	120.1 (12)
C5—C6—C7	120.3 (10)	C19—C18—H18A	119.9
C1—C6—C7	122.8 (9)	C17—C18—H18A	119.9
C8—C7—C6	127.4 (9)	C18—C19—C20	120.7 (12)
C8—C7—H7A	116.3	C18—C19—H19A	119.6
C6—C7—H7A	116.3	C20—C19—H19A	119.6
C7—C8—C9	121.4 (9)	C21—C20—C19	120.0 (12)
C7—C8—H8A	119.3	C21—C20—H20A	120.0
C9—C8—H8A	119.3	C19—C20—H20A	120.0
N10—C9—C8	123.0 (8)	C20—C21—C22	119.5 (12)
N10—C9—H9A	118.5	C20—C21—H21A	120.3
C8—C9—H9A	118.5	C22—C21—H21A	120.3
C9—N10—C11	118.7 (7)	C21—C22—C17	121.5 (11)
C9—N10—Cu1	135.5 (6)	C21—C22—H22A	119.3
C11—N10—Cu1	105.5 (5)	C17—C22—H22A	119.3
N10—C11—C12	109.6 (7)

Symmetry code: (i) −x, −y, −z+1.