Bis[2,6-bis­(3,5-dimethyl-1H-pyrazol-1-yl)pyridine]di-μ3-iodido-diiodidotetra­copper(I)

Jia, C.-X.

doi:10.1107/S1600536811026468

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1059

doi:10.1107/S1600536811026468

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Bis[2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine]di-μ₃-iodido-diiodidotetracopper(I)

Chun-Xiao Jia ^a ^*

^aDepartment of Chemistry, DeZhou University, De Zhou, Shan Dong 253023, People's Republic of China
^*Correspondence e-mail: jiachunxiao@yahoo.com.cn

(Received 13 June 2011; accepted 4 July 2011; online 9 July 2011)

In the title centrosymmetric tetranuclear complex, [Cu₄I₄(C₁₅H₁₇N₅)₂], the two distinct Cu^I atoms adopt similar tetrahedral arrangements, each being ligated by two I atoms, and two N atoms from one 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine ligand. In the crystal, there are no hydrogen bonds present, and only very weak π–π interactions are observed [centroid–centroid distance = 3.985 (4) Å], which connect neighbouring tetranuclear units into a chain motif along the b axis.

Related literature

For related structures and background references, see: Carina et al. (1998 ); Constable et al. (1994 ); Piguet et al. (1989 ); Solanki et al. (1999 ); Lazarou et al. (2009 , 2010 ). For tetrahedral geometry, see: Halcrow et al. (1997 ).

Experimental

Crystal data

[Cu₄I₄(C₁₅H₁₇N₅)₂]
M_r = 1296.47
Monoclinic, P 2₁ /c
a = 10.196 (2) Å
b = 11.425 (2) Å
c = 16.572 (3) Å
β = 98.67 (3)°
V = 1908.3 (7) Å³
Z = 2
Mo Kα radiation
μ = 5.47 mm⁻¹
T = 296 K
0.23 × 0.20 × 0.19 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.366, T_max = 0.423
18181 measured reflections
3484 independent reflections
3090 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.144
S = 1.04
3484 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026468/su2284sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026468/su2284Isup2.hkl

checkCIF report

Comment top

The study of dimeric double helical complexes generated from copper(I) salts and 2,6-bis(imidazol-2-yl)pyridine ligands demonstrates that, the variable copper(I) coordination geometries in the helicates can exhibit different connectivity patterns, such as {4+2}, {2+2+2}, and {3+3} motifs (Carina et al., 1998; Constable et al., 1994; Piguet et al., 1989; Solanki et al., 1999). Recently, some auxiliary ligands have also been introduced into these coordination systems (Lazarou et al., 2009, 2010). Here, we used iodine ions to bridge the copper(I) ions, which resulted in the tetranuclear coordination motif of the title compound (Fig. 1).

There are two crystallographic distinct copper(I) centers in this complex, which display similar coordination environments. Each metal center is linked to two nitrogen atoms from one 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine ligand, and to two iodine ions to give the tetrahedral coordination geometry. Both the geometries at atoms Cu1 and Cu2 are slightly flattened, the dihedral angles between the planes of the donors [Cu,N,N] and [Cu,I,I] are 75.2 (2)° and 81.46 (19)°, for atoms Cu1 and Cu2, respectively; they should be 90° for an 'ideal' tetrahedron (Halcrow et al., 1997). Paired copper(I) atoms are ligated to one 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine ligand acting as a tridentate ligand, forming two five membered chelate rings. In favour of the bridging role of the I1 donor is the fact that the binuclear coordination units, which are interlinked via an invesion center into a tetranuclear entity, feature two kinds of coordination squares with the compositions of Cu₂IN and Cu₂I₂.

In the crystal, there exists a very weak π–π interaction, between the pyridyl ring (N1/C1—C5) and a pyrazol ring (N2,N3/C6—C8) from an adjacent molecule, with a centroid to centroid distance of 3.985 (4) Å and a dihedral angle of 24.72° (Fig. 2).

Related literature top

For related structures and background references, see: Carina et al. (1998); Constable et al. (1994); Piguet et al. (1989); Solanki et al. (1999); Lazarou et al. (2009, 2010). For tetrahedral geometry, see: Halcrow et al. (1997).

Experimental top

A mixture of CuI (15 mg, 0.1 mmol) and 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine (13 mg, 0.05 mmol) was dissolved in MeCN (2 ml) in air. A light green solution was obtained, which was transferred into a Pyrex glass tube. It was then sealed and heated to 393 K for 48 h, and cooled to room temperature at a rate of 5 °C/h. Blue blocks of the title complex were formed. They were collected by filtration, washed with MeCN/Et₂O (v/v = 1: 4) and dried in air.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level [Symmetry code: (a) -x+2, -y, -z].
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The π–π interactions are shown as green dashed lines.

Bis[2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)pyridine]di-µ₃-iodido- diiodidotetracopper(I) top

Crystal data top

[Cu₄I₄(C₁₅H₁₇N₅)₂]	F(000) = 1224
M_r = 1296.47	D_x = 2.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6904 reflections
a = 10.196 (2) Å	θ = 3.1–25.4°
b = 11.425 (2) Å	µ = 5.47 mm⁻¹
c = 16.572 (3) Å	T = 296 K
β = 98.67 (3)°	Block, yellow
V = 1908.3 (7) Å³	0.23 × 0.20 × 0.19 mm
Z = 2

Data collection top

Rigaku Mercury diffractometer	3484 independent reflections
Radiation source: fine-focus sealed tube	3090 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 25.4°, θ_min = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −12→12
T_min = 0.366, T_max = 0.423	k = −13→13
18181 measured reflections	l = −18→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3484 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[Cu₄I₄(C₁₅H₁₇N₅)₂]	V = 1908.3 (7) Å³
M_r = 1296.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.196 (2) Å	µ = 5.47 mm⁻¹
b = 11.425 (2) Å	T = 296 K
c = 16.572 (3) Å	0.23 × 0.20 × 0.19 mm
β = 98.67 (3)°

Data collection top

Rigaku Mercury diffractometer	3484 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	3090 reflections with I > 2σ(I)
T_min = 0.366, T_max = 0.423	R_int = 0.044
18181 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.04	Δρ_max = 0.79 e Å⁻³
3484 reflections	Δρ_min = −1.14 e Å⁻³
221 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
I1	0.89222 (5)	0.01954 (4)	0.10655 (3)	0.0451 (2)
I2	0.69949 (5)	−0.31427 (5)	0.14285 (3)	0.0560 (2)
Cu1	1.09482 (9)	0.06814 (8)	0.03673 (5)	0.0496 (3)
Cu2	0.88858 (8)	−0.21963 (8)	0.09155 (6)	0.0505 (3)
N1	1.0760 (5)	0.2853 (4)	0.0443 (3)	0.0330 (16)
N2	0.8750 (5)	0.3195 (4)	−0.0368 (3)	0.0317 (16)
N3	0.9228 (5)	0.2702 (4)	−0.1017 (3)	0.0327 (16)
N4	1.2814 (5)	0.2399 (4)	0.1183 (3)	0.0370 (17)
N5	1.2690 (5)	0.1243 (4)	0.0920 (3)	0.0390 (17)
C1	1.1655 (6)	0.3094 (5)	0.1094 (4)	0.0338 (17)
C2	1.1460 (6)	0.3916 (5)	0.1671 (4)	0.0373 (19)
C3	1.0338 (7)	0.4591 (5)	0.1528 (4)	0.0394 (19)
C4	0.9396 (6)	0.4392 (5)	0.0853 (4)	0.0353 (17)
C5	0.9650 (6)	0.3487 (5)	0.0339 (3)	0.0329 (17)
C6	0.7411 (6)	0.3407 (6)	−0.0557 (4)	0.0385 (19)
C7	0.7065 (6)	0.3060 (6)	−0.1340 (4)	0.0392 (19)
C8	0.8209 (6)	0.2622 (5)	−0.1604 (4)	0.0364 (17)
C9	0.6551 (7)	0.3812 (8)	0.0042 (5)	0.061 (3)
C10	0.8402 (7)	0.2080 (7)	−0.2401 (4)	0.050 (2)
C11	1.4084 (6)	0.2670 (6)	0.1455 (4)	0.0409 (19)
C12	1.4805 (7)	0.1673 (6)	0.1367 (5)	0.050 (2)
C13	1.3894 (7)	0.0821 (6)	0.1042 (4)	0.046 (2)
C14	1.4556 (8)	0.3854 (7)	0.1752 (5)	0.059 (3)
C15	1.4186 (10)	−0.0425 (7)	0.0865 (6)	0.074 (3)
H2	1.20710	0.40110	0.21430	0.0450*
H3	1.02100	0.51880	0.18890	0.0470*
H4	0.86290	0.48410	0.07480	0.0420*
H7	0.62240	0.31040	−0.16460	0.0470*
H9A	0.64980	0.46510	0.00300	0.0910*
H9B	0.69250	0.35580	0.05800	0.0910*
H9C	0.56790	0.34870	−0.01000	0.0910*
H10A	0.93010	0.21970	−0.24900	0.0750*
H10B	0.78090	0.24390	−0.28360	0.0750*
H10C	0.82190	0.12560	−0.23880	0.0750*
H12	1.57190	0.15840	0.14980	0.0610*
H14A	1.40540	0.44440	0.14280	0.0890*
H14B	1.54790	0.39370	0.17060	0.0890*
H14C	1.44390	0.39430	0.23130	0.0890*
H15A	1.37580	−0.09290	0.12080	0.1100*
H15B	1.51270	−0.05530	0.09690	0.1100*
H15C	1.38620	−0.05940	0.03030	0.1100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0518 (3)	0.0381 (3)	0.0481 (3)	−0.0022 (2)	0.0159 (2)	−0.0044 (2)
I2	0.0392 (3)	0.0522 (3)	0.0810 (4)	−0.0087 (2)	0.0229 (3)	−0.0150 (2)
Cu1	0.0423 (5)	0.0509 (5)	0.0544 (5)	−0.0101 (4)	0.0032 (4)	−0.0077 (4)
Cu2	0.0319 (5)	0.0540 (6)	0.0667 (6)	0.0032 (4)	0.0112 (4)	0.0004 (4)
N1	0.027 (3)	0.038 (3)	0.034 (2)	0.000 (2)	0.005 (2)	−0.003 (2)
N2	0.027 (3)	0.037 (3)	0.032 (2)	0.000 (2)	0.007 (2)	0.001 (2)
N3	0.030 (3)	0.036 (3)	0.033 (2)	0.001 (2)	0.008 (2)	0.003 (2)
N4	0.035 (3)	0.036 (3)	0.039 (3)	−0.002 (2)	0.002 (2)	−0.003 (2)
N5	0.034 (3)	0.031 (3)	0.051 (3)	0.003 (2)	0.003 (2)	0.002 (2)
C1	0.033 (3)	0.034 (3)	0.035 (3)	0.000 (3)	0.007 (3)	0.003 (3)
C2	0.040 (4)	0.036 (3)	0.035 (3)	−0.005 (3)	0.003 (3)	0.001 (3)
C3	0.044 (4)	0.031 (3)	0.045 (3)	0.000 (3)	0.013 (3)	−0.003 (3)
C4	0.037 (3)	0.032 (3)	0.037 (3)	0.000 (3)	0.006 (3)	0.000 (3)
C5	0.031 (3)	0.031 (3)	0.036 (3)	−0.004 (3)	0.003 (3)	−0.003 (2)
C6	0.029 (3)	0.039 (3)	0.049 (4)	0.006 (3)	0.011 (3)	−0.004 (3)
C7	0.031 (3)	0.039 (4)	0.045 (3)	0.002 (3)	−0.003 (3)	0.001 (3)
C8	0.033 (3)	0.031 (3)	0.044 (3)	0.002 (3)	0.002 (3)	−0.009 (3)
C9	0.033 (4)	0.085 (6)	0.066 (5)	−0.003 (4)	0.012 (4)	−0.018 (4)
C10	0.047 (4)	0.064 (5)	0.038 (3)	0.009 (4)	0.001 (3)	−0.010 (3)
C11	0.029 (3)	0.048 (4)	0.043 (3)	−0.009 (3)	−0.003 (3)	−0.005 (3)
C12	0.031 (4)	0.052 (4)	0.066 (4)	0.004 (3)	0.000 (3)	0.006 (4)
C13	0.045 (4)	0.039 (4)	0.052 (4)	−0.003 (3)	0.005 (3)	0.006 (3)
C14	0.049 (5)	0.054 (5)	0.072 (5)	−0.011 (4)	0.002 (4)	−0.008 (4)
C15	0.073 (6)	0.046 (5)	0.101 (7)	0.011 (4)	0.010 (5)	−0.001 (5)

Geometric parameters (Å, º) top

I1—Cu1	2.5758 (12)	C7—C8	1.399 (9)
I1—Cu2	2.7435 (12)	C8—C10	1.498 (9)
I1—Cu1ⁱ	2.5988 (11)	C11—C12	1.375 (10)
I2—Cu2	2.4704 (11)	C11—C14	1.494 (11)
Cu1—N1	2.493 (5)	C12—C13	1.396 (10)
Cu1—N5	1.978 (5)	C13—C15	1.493 (11)
Cu2—N1ⁱ	2.451 (5)	C2—H2	0.9300
Cu2—N3ⁱ	1.991 (5)	C3—H3	0.9300
N1—C1	1.333 (8)	C4—H4	0.9300
N1—C5	1.333 (8)	C7—H7	0.9300
N2—N3	1.367 (7)	C9—H9A	0.9600
N2—C5	1.415 (7)	C9—H9B	0.9600
N2—C6	1.375 (8)	C9—H9C	0.9600
N3—C8	1.315 (8)	C10—H10A	0.9600
N4—N5	1.391 (7)	C10—H10B	0.9600
N4—C1	1.413 (8)	C10—H10C	0.9600
N4—C11	1.342 (8)	C12—H12	0.9300
N5—C13	1.306 (9)	C14—H14A	0.9600
C1—C2	1.376 (9)	C14—H14B	0.9600
C2—C3	1.370 (9)	C14—H14C	0.9600
C3—C4	1.379 (9)	C15—H15A	0.9600
C4—C5	1.389 (8)	C15—H15B	0.9600
C6—C7	1.352 (9)	C15—H15C	0.9600
C6—C9	1.494 (10)

Cu1—I1—Cu2	100.07 (4)	C6—C7—C8	107.2 (6)
Cu1—I1—Cu1ⁱ	61.18 (4)	N3—C8—C7	110.3 (6)
Cu1ⁱ—I1—Cu2	62.30 (4)	N3—C8—C10	119.1 (6)
I1—Cu1—N1	96.83 (13)	C7—C8—C10	130.6 (6)
I1—Cu1—N5	125.92 (15)	N4—C11—C12	106.1 (6)
I1—Cu1—I1ⁱ	118.82 (5)	N4—C11—C14	124.5 (6)
N1—Cu1—N5	74.01 (18)	C12—C11—C14	129.4 (6)
I1ⁱ—Cu1—N1	116.39 (12)	C11—C12—C13	106.5 (6)
I1ⁱ—Cu1—N5	112.48 (15)	N5—C13—C12	111.0 (6)
I1—Cu2—I2	113.91 (5)	N5—C13—C15	122.2 (7)
I1—Cu2—N1ⁱ	112.72 (12)	C12—C13—C15	126.9 (7)
I1—Cu2—N3ⁱ	106.36 (14)	C1—C2—H2	121.00
I2—Cu2—N1ⁱ	114.38 (13)	C3—C2—H2	121.00
I2—Cu2—N3ⁱ	129.64 (15)	C2—C3—H3	120.00
N1ⁱ—Cu2—N3ⁱ	73.41 (19)	C4—C3—H3	120.00
Cu1—N1—C1	101.4 (4)	C3—C4—H4	122.00
Cu1—N1—C5	127.2 (4)	C5—C4—H4	122.00
Cu1—N1—Cu2ⁱ	68.04 (13)	C6—C7—H7	126.00
C1—N1—C5	117.2 (5)	C8—C7—H7	126.00
Cu2ⁱ—N1—C1	129.0 (4)	C6—C9—H9A	109.00
Cu2ⁱ—N1—C5	106.7 (3)	C6—C9—H9B	109.00
N3—N2—C5	119.0 (5)	C6—C9—H9C	109.00
N3—N2—C6	110.7 (5)	H9A—C9—H9B	110.00
C5—N2—C6	130.1 (5)	H9A—C9—H9C	110.00
N2—N3—C8	106.0 (5)	H9B—C9—H9C	110.00
Cu2ⁱ—N3—N2	120.5 (4)	C8—C10—H10A	109.00
Cu2ⁱ—N3—C8	133.5 (4)	C8—C10—H10B	109.00
N5—N4—C1	117.8 (5)	C8—C10—H10C	109.00
N5—N4—C11	111.2 (5)	H10A—C10—H10B	109.00
C1—N4—C11	130.9 (5)	H10A—C10—H10C	109.00
Cu1—N5—N4	119.1 (4)	H10B—C10—H10C	109.00
Cu1—N5—C13	135.2 (4)	C11—C12—H12	127.00
N4—N5—C13	105.3 (5)	C13—C12—H12	127.00
N1—C1—N4	115.4 (5)	C11—C14—H14A	109.00
N1—C1—C2	123.4 (6)	C11—C14—H14B	110.00
N4—C1—C2	121.2 (6)	C11—C14—H14C	110.00
C1—C2—C3	117.9 (6)	H14A—C14—H14B	109.00
C2—C3—C4	120.6 (6)	H14A—C14—H14C	109.00
C3—C4—C5	116.7 (6)	H14B—C14—H14C	109.00
N1—C5—N2	114.3 (5)	C13—C15—H15A	110.00
N1—C5—C4	124.0 (5)	C13—C15—H15B	109.00
N2—C5—C4	121.7 (5)	C13—C15—H15C	109.00
N2—C6—C7	105.9 (5)	H15A—C15—H15B	110.00
N2—C6—C9	124.4 (6)	H15A—C15—H15C	109.00
C7—C6—C9	129.4 (6)	H15B—C15—H15C	109.00

Cu2—I1—Cu1—N1	175.69 (12)	C1—N1—C5—N2	179.3 (5)
Cu1ⁱ—I1—Cu1—N1	125.23 (12)	C1—N1—C5—C4	1.8 (9)
Cu2—I1—Cu1—N5	−109.13 (18)	Cu2ⁱ—N1—C5—N2	26.1 (5)
Cu1ⁱ—I1—Cu1—N5	−159.60 (18)	Cu2ⁱ—N1—C5—C4	−151.4 (5)
Cu2—I1—Cu1—I1ⁱ	50.47 (5)	C5—N2—N3—C8	−174.6 (5)
Cu1ⁱ—I1—Cu1—I1ⁱ	0.02 (10)	C5—N2—N3—Cu2ⁱ	8.5 (6)
Cu1ⁱ—I1ⁱ—Cu1—I1	0.02 (11)	C6—N2—N3—C8	0.8 (6)
Cu2ⁱ—I1ⁱ—Cu1—I1	120.94 (6)	C6—N2—N3—Cu2ⁱ	−176.1 (4)
Cu1ⁱ—I1ⁱ—Cu1—N1	−115.12 (14)	N3—N2—C5—N1	−25.8 (7)
Cu2ⁱ—I1ⁱ—Cu1—N1	5.83 (14)	N3—N2—C5—C4	151.8 (5)
Cu1ⁱ—I1ⁱ—Cu1—N5	162.21 (16)	C6—N2—C5—N1	159.9 (6)
Cu2ⁱ—I1ⁱ—Cu1—N5	−76.85 (15)	C6—N2—C5—C4	−22.5 (9)
Cu1—I1—Cu2—I2	−176.47 (5)	N3—N2—C6—C7	−1.2 (7)
Cu1ⁱ—I1—Cu2—I2	−126.72 (6)	N3—N2—C6—C9	172.7 (6)
Cu1—I1—Cu2—N1ⁱ	−44.00 (14)	C5—N2—C6—C7	173.5 (6)
Cu1ⁱ—I1—Cu2—N1ⁱ	5.75 (14)	C5—N2—C6—C9	−12.7 (11)
Cu1—I1—Cu2—N3ⁱ	34.49 (16)	N2—N3—C8—C7	−0.1 (7)
Cu1ⁱ—I1—Cu2—N3ⁱ	84.24 (16)	N2—N3—C8—C10	−178.4 (5)
N1—Cu1—N5—C13	−159.0 (6)	Cu2ⁱ—N3—C8—C7	176.3 (4)
I1ⁱ—Cu1—N5—N4	124.0 (4)	Cu2ⁱ—N3—C8—C10	−2.0 (9)
I1ⁱ—Cu1—N5—C13	−46.6 (6)	C1—N4—N5—Cu1	4.6 (7)
I1—Cu1—N1—C1	99.2 (4)	C1—N4—N5—C13	177.7 (5)
I1—Cu1—N1—C5	−38.4 (5)	C11—N4—N5—Cu1	−172.7 (4)
I1—Cu1—N1—Cu2ⁱ	−133.19 (9)	C11—N4—N5—C13	0.5 (7)
N5—Cu1—N1—C1	−26.3 (4)	N5—N4—C1—N1	−33.3 (7)
N5—Cu1—N1—C5	−163.9 (5)	N5—N4—C1—C2	143.6 (6)
N5—Cu1—N1—Cu2ⁱ	101.33 (18)	C11—N4—C1—N1	143.3 (6)
I1ⁱ—Cu1—N1—C1	−133.9 (3)	C11—N4—C1—C2	−39.8 (10)
I1ⁱ—Cu1—N1—C5	88.5 (5)	N5—N4—C11—C12	0.1 (7)
I1ⁱ—Cu1—N1—Cu2ⁱ	−6.23 (15)	N5—N4—C11—C14	177.7 (6)
I1—Cu1—N5—N4	−75.3 (4)	C1—N4—C11—C12	−176.7 (6)
I1—Cu1—N5—C13	114.2 (6)	C1—N4—C11—C14	1.0 (11)
N1—Cu1—N5—N4	11.6 (4)	Cu1—N5—C13—C12	170.7 (5)
I1—Cu2—N1ⁱ—Cu1ⁱ	−5.73 (14)	Cu1—N5—C13—C15	−10.8 (10)
I1—Cu2—N1ⁱ—C1ⁱ	−92.8 (5)	N4—N5—C13—C12	−0.8 (7)
I1—Cu2—N1ⁱ—C5ⁱ	118.3 (3)	N4—N5—C13—C15	177.7 (6)
I2—Cu2—N1ⁱ—Cu1ⁱ	126.52 (8)	N1—C1—C2—C3	−6.0 (9)
I2—Cu2—N1ⁱ—C1ⁱ	39.5 (5)	N4—C1—C2—C3	177.4 (6)
I2—Cu2—N1ⁱ—C5ⁱ	−109.5 (4)	C1—C2—C3—C4	4.3 (9)
I1—Cu2—N3ⁱ—N2ⁱ	−114.1 (4)	C2—C3—C4—C5	−0.1 (9)
I1—Cu2—N3ⁱ—C8ⁱ	61.9 (6)	C3—C4—C5—N1	−3.2 (9)
I2—Cu2—N3ⁱ—N2ⁱ	103.6 (4)	C3—C4—C5—N2	179.4 (5)
I2—Cu2—N3ⁱ—C8ⁱ	−80.5 (6)	N2—C6—C7—C8	1.1 (7)
Cu1—N1—C1—N4	36.9 (6)	C9—C6—C7—C8	−172.4 (7)
Cu1—N1—C1—C2	−139.9 (5)	C6—C7—C8—N3	−0.6 (8)
C5—N1—C1—N4	179.8 (5)	C6—C7—C8—C10	177.4 (7)
C5—N1—C1—C2	3.0 (9)	N4—C11—C12—C13	−0.6 (8)
Cu2ⁱ—N1—C1—N4	−34.0 (7)	C14—C11—C12—C13	−178.1 (7)
Cu2ⁱ—N1—C1—C2	149.3 (5)	C11—C12—C13—N5	0.9 (8)
Cu1—N1—C5—N2	−48.7 (6)	C11—C12—C13—C15	−177.5 (7)
Cu1—N1—C5—C4	133.8 (5)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cu₄I₄(C₁₅H₁₇N₅)₂]
M_r	1296.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.196 (2), 11.425 (2), 16.572 (3)
β (°)	98.67 (3)
V (Å³)	1908.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.47
Crystal size (mm)	0.23 × 0.20 × 0.19

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.366, 0.423
No. of measured, independent and observed [I > 2σ(I)] reflections	18181, 3484, 3090
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.144, 1.04
No. of reflections	3484
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −1.14

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Carina, R. F., Williams, A. F. & Riguet, C. (1998). Helv. Chim. Acta, 81, 548–557. Web of Science CrossRef CAS Google Scholar
Constable, E. C., Edwards, A. J., Hannon, M. J. & Raithby, P. R. (1994). J. Chem. Soc. Chem. Commun. pp. 1991–1992. CrossRef Web of Science Google Scholar
Halcrow, M. A., Cromhout, N. L. & Raithby, P. R. (1997). Polyhedron, 16, 4257–4264. CSD CrossRef CAS Web of Science Google Scholar
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. Google Scholar
Lazarou, K. N., Chadjistamatis, I., Terzis, A., Perlepes, S. P. & Raptopoulou, C. P. (2010). Polyhedron, 29, 1870–1879. Web of Science CSD CrossRef CAS Google Scholar
Lazarou, K. N., Raptopoulou, C. P., Perlepes, S. P. & Psycharis, V. (2009). Polyhedron, 28, 3185–3192. Web of Science CSD CrossRef CAS Google Scholar
Piguet, C., Bernardinelli, G. & Williams, A. F. (1989). Inorg. Chem. 28, 2920–2925. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solanki, N. K., Wheatley, E. H., Radojevic, S., McPartlin, M. & Halcrow, M. A. (1999). J. Chem. Soc. Dalton Trans. pp. 521–523. Web of Science CSD CrossRef Google Scholar

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