catena-Poly[[[iodidocopper(I)]-{μ-N-[(pyridin-2-yl-κN)methyl­idene]pyridin-3-amine-κ2N3:N1}] acetonitrile hemisolvate]

Mahmoudi, A.; Dehghanpour, S.; Babakhodaverdi, M.

doi:10.1107/S1600536812037270

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1277-m1278

https://doi.org/10.1107/S1600536812037270

Open

access

catena-Poly[[[iodidocopper(I)]-{μ-N-[(pyridin-2-yl-κN)methylidene]pyridin-3-amine-κ²N³:N¹}] acetonitrile hemisolvate]

Ali Mahmoudi,^a ^* Saeed Dehghanpour ^b and Mojtaba Babakhodaverdi ^a

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, and ^bDepartment of Chemistry, Alzahra University, Tehran, Iran
^*Correspondence e-mail: Mahmoudi_Ali@yahoo.com

(Received 16 July 2012; accepted 29 August 2012; online 19 September 2012)

In the asymmetric unit of the title polymeric complex, {[CuI(C₁₁H₉N₃)]·0.5CH₃CN}_n, there are two Cu^I atoms, two N-[(pyridin-2-yl-κN)methylidene]pyridin-3-amine (PyPy) ligands and two I atoms. Both Cu^I atoms have a distorted tetrahedral geometry, each being coordinated by one I atom, two N atoms of one PyPy ligand and one N atom from an adjacent PyPy ligand. In the crystal, infinite helical chains of [Cu₂(PyPy)₂]_n are formed propagating along the b axis. These chains are linked via weak C—H⋯I hydrogen bonds and π–π stacking interactions [shortest centroid–centroid distance = 3.2727 (14) Å]. During the refinement, electron-density peaks were located that were believed to be highly disordered solvent molecules (possibly acetonitrile). The SQUEEZE option in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155] indicated there were solvent cavities with a total volume of 196 Å³ containing approximately 60 electrons per unit cell, which equated to one molecule of acetonitrile per asymmetric unit.

Related literature

For related structures and applications of coordination polymers, see: Moulton & Zaworotko (2001 ); Fei et al. (2000 ). For the synthesis of the title ligand, see: Dehghanpour et al. (2009 ).

Experimental

Crystal data

[CuI(C₁₁H₉N₃)]·0.5C₂H₃N
M_r = 394.18
Monoclinic, P 2₁ /n
a = 7.1800 (2) Å
b = 13.2303 (7) Å
c = 27.9383 (13) Å
β = 90.741 (3)°
V = 2653.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 3.96 mm⁻¹
T = 150 K
0.17 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.569, T_max = 0.733
19063 measured reflections
4676 independent reflections
2627 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.178
S = 1.02
4676 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 1.39 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯I1ⁱ	0.95	3.03	3.789 (12)	138
C20—H20A⋯I1ⁱⁱ	0.95	3.14	4.025 (12)	156
C17—H17A⋯I2ⁱⁱⁱ	0.95	3.16	4.011 (11)	149
Symmetry codes: (i) x, y-1, z; (ii) -x+3, -y-1, -z+1; (iii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037270/su2480sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037270/su2480Isup2.hkl

checkCIF report

Comment top

In recent years, coordination polymers have received much attention due to their variety of architectures and the potential applications as functional materials (Moulton & Zaworotko, 2001). Early reports have shown that nitrogen heterocyclic ligands have been employed in the synthesis of many novel structures (Fei et al., 2000). Here, we report on the synthetic and crystal structure of a novel copper iodide complex based on the ligand pyridin-3-ylpyridin-2-ylmethyleneamine (PyPy).

The asymmetric unit of the title compound, Fig. 1, contains two Cu^I atoms, two pyridin-3-ylpyridin-2-ylmethyleneamine (Dehghanpour et al., 2009) ligands, and two I atoms, Each Cu⁺ atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from one PyPy ligand, one N atom from an adjacent PyPy ligand and one I atom. Each PyPy ligand chelates the Cu atom (via N, N' atoms) and also bridges to another Cu atom (with N" atom), resulting in the formation of chains propagating along the b axis.

The two ligands in the asymmetric unit are nearly planar. In ligand A the interplanar angles between chelate ring (N2/C6/C7/N3) and pyridine ring (lN3/C7-C11) is 2.11 (3)°, while for ligand B [chelate ring N5/C17/C18/N6 and pyridine ring N6/C18-C22] the same angle is 5.82 (4)°. In ligand A the two pyridine rings (N1/C1-C5 and N3/C7-C11) are inclined to one another by 12.11 (4)°. In ligand B the two pyridine rings (N6/C18-C22 and N4/C12-5C16) are inclined to one another by 7.49 (3)°. However, the interplanar angle between two ligand mean planes (A and B) is 52.82 (1)°.

In the crystal, these chains interact via π–π interactions between adjacent, inversion replated PyPy ligands The shortest distance of 3.2727 (14) Å [C15-C19 ring, symmetry code: (iii) = -x + 3, -y - 1, -z + 1] is observed between two inversion related ligands. These chains are further connected through C—H···I interactions (Table 1 and Fig 2.).

Related literature top

For related structures and applications of coordination polymers, see: Moulton & Zaworotko (2001); Fei et al. (2000). For the synthesis of the title ligand, see: Dehghanpour et al. (2009).

Experimental top

The title complex was prepared by the reaction of CuI (19.1 mg, 0.1 mmol) and pyridin-3-ylpyridin-2-ylmethyleneamine (18.3 mg, 0.1 mmol) in 20 ml of acetonitrile at room temperature. Crystals of the title compound, suitable for X-ray analysis, were obtained by slow evaporation of the solvent at rt.

Structure description top

For related structures and applications of coordination polymers, see: Moulton & Zaworotko (2001); Fei et al. (2000). For the synthesis of the title ligand, see: Dehghanpour et al. (2009).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title complex, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level [Symmetry codes: (ix) 5/2 - x, -1/2 + y, 1/2 - z; (x) x, -1 + y, z; (xiii) 5/2 - x, 1/2 + y, 1/2 - z].
	Fig. 2. A view of the π–π interactions and C—H···I hydrogen bonds (dotted lines) in the crystal structure of the title compound.

catena-Poly[[[iodidocopper(I)]-{µ-N-[(pyridin-2- yl-κN)methylidene]pyridin-3-amine-κ²N³:N¹}] acetonitrile monosolvate] top

Crystal data top

[CuI(C₁₁H₉N₃)]·0.5C₂H₃N	F(000) = 1512
M_r = 394.18	D_x = 1.973 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19063 reflections
a = 7.1800 (2) Å	θ = 2.5–25.0°
b = 13.2303 (7) Å	µ = 3.96 mm⁻¹
c = 27.9383 (13) Å	T = 150 K
β = 90.741 (3)°	Block, brown
V = 2653.7 (2) Å³	0.17 × 0.12 × 0.10 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	4676 independent reflections
Radiation source: fine-focus sealed tube	2627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.104
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
φ scans and ω scans with κ offsets	h = −8→8
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −15→15
T_min = 0.569, T_max = 0.733	l = −33→33
19063 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0943P)²] where P = (F_o² + 2F_c²)/3
4676 reflections	(Δ/σ)_max = 0.002
289 parameters	Δρ_max = 1.39 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

[CuI(C₁₁H₉N₃)]·0.5C₂H₃N	V = 2653.7 (2) Å³
M_r = 394.18	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1800 (2) Å	µ = 3.96 mm⁻¹
b = 13.2303 (7) Å	T = 150 K
c = 27.9383 (13) Å	0.17 × 0.12 × 0.10 mm
β = 90.741 (3)°

Data collection top

Nonius KappaCCD diffractometer	4676 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2627 reflections with I > 2σ(I)
T_min = 0.569, T_max = 0.733	R_int = 0.104
19063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.02	Δρ_max = 1.39 e Å⁻³
4676 reflections	Δρ_min = −1.24 e Å⁻³
289 parameters

Special details top

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
I1	1.60988 (13)	−0.00459 (7)	0.36787 (3)	0.0589 (3)
I2	0.61501 (9)	−0.05499 (6)	0.10018 (2)	0.0389 (3)
Cu1	1.50363 (18)	−0.17127 (11)	0.32943 (4)	0.0400 (4)
Cu2	0.97229 (16)	−0.07450 (11)	0.10723 (4)	0.0365 (4)
N1	1.0526 (12)	−0.0684 (7)	0.1767 (3)	0.039 (2)
N2	1.4312 (11)	−0.1559 (6)	0.2576 (3)	0.032 (2)
N3	1.7228 (11)	−0.2492 (7)	0.2989 (3)	0.039 (2)
N4	1.3514 (11)	−0.2392 (7)	0.3785 (3)	0.036 (2)
N5	1.3643 (10)	−0.4852 (7)	0.4384 (3)	0.029 (2)
N6	1.4522 (11)	−0.6811 (7)	0.4423 (3)	0.037 (2)
C1	0.9411 (16)	−0.0224 (9)	0.2091 (4)	0.042 (3)
H1A	0.8262	0.0063	0.1987	0.051*
C2	0.9913 (15)	−0.0165 (9)	0.2567 (4)	0.044 (3)
H2A	0.9147	0.0176	0.2790	0.053*
C3	1.1567 (14)	−0.0616 (8)	0.2713 (4)	0.038 (3)
H3A	1.1948	−0.0593	0.3040	0.045*
C4	1.2640 (14)	−0.1092 (8)	0.2385 (4)	0.037 (3)
C5	1.2109 (13)	−0.1129 (8)	0.1925 (3)	0.030 (2)
H5A	1.2867	−0.1478	0.1703	0.036*
C6	1.5589 (15)	−0.1921 (8)	0.2304 (4)	0.036 (3)
H6A	1.5464	−0.1853	0.1966	0.043*
C7	1.7202 (14)	−0.2428 (8)	0.2502 (3)	0.034 (3)
C8	1.8553 (15)	−0.2858 (9)	0.2230 (4)	0.042 (3)
H8A	1.8478	−0.2806	0.1891	0.050*
C9	2.0017 (16)	−0.3364 (9)	0.2440 (4)	0.044 (3)
H9A	2.0955	−0.3666	0.2250	0.053*
C10	2.0096 (15)	−0.3424 (9)	0.2930 (4)	0.049 (3)
H10A	2.1101	−0.3757	0.3088	0.059*
C11	1.8675 (14)	−0.2987 (9)	0.3186 (4)	0.045 (3)
H11A	1.8725	−0.3041	0.3525	0.054*
C12	1.2362 (14)	−0.1885 (9)	0.4062 (4)	0.040 (3)
H12A	1.2122	−0.1196	0.3988	0.049*
C13	1.1467 (14)	−0.2310 (9)	0.4462 (4)	0.045 (3)
H13A	1.0588	−0.1928	0.4638	0.054*
C14	1.1884 (13)	−0.3277 (9)	0.4593 (4)	0.040 (3)
H14A	1.1356	−0.3570	0.4870	0.048*
C15	1.3101 (13)	−0.3826 (9)	0.4310 (3)	0.033 (3)
C16	1.3879 (12)	−0.3373 (8)	0.3914 (3)	0.031 (3)
H16A	1.4704	−0.3758	0.3724	0.037*
C17	1.2990 (12)	−0.5374 (8)	0.4725 (4)	0.033 (3)
H17A	1.2150	−0.5068	0.4941	0.040*
C18	1.3492 (14)	−0.6418 (8)	0.4791 (4)	0.035 (3)
C19	1.3045 (14)	−0.6992 (9)	0.5186 (4)	0.042 (3)
H19A	1.2341	−0.6695	0.5435	0.051*
C20	1.3595 (14)	−0.7977 (10)	0.5228 (4)	0.043 (3)
H20A	1.3260	−0.8378	0.5496	0.052*
C21	1.4685 (16)	−0.8371 (9)	0.4854 (4)	0.050 (3)
H21A	1.5134	−0.9045	0.4872	0.060*
C22	1.5098 (16)	−0.7777 (9)	0.4462 (4)	0.049 (3)
H22A	1.5814	−0.8060	0.4212	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0911 (7)	0.0473 (6)	0.0383 (5)	−0.0199 (5)	−0.0001 (4)	−0.0023 (4)
I2	0.0311 (4)	0.0564 (6)	0.0292 (4)	0.0023 (3)	−0.0015 (3)	0.0035 (4)
Cu1	0.0506 (8)	0.0436 (9)	0.0259 (7)	0.0010 (6)	0.0002 (6)	0.0026 (6)
Cu2	0.0346 (7)	0.0508 (10)	0.0241 (7)	0.0002 (6)	0.0001 (5)	0.0010 (6)
N1	0.048 (6)	0.047 (6)	0.023 (5)	0.004 (5)	−0.001 (4)	−0.002 (4)
N2	0.037 (5)	0.034 (6)	0.024 (5)	0.001 (4)	−0.005 (4)	0.007 (4)
N3	0.031 (5)	0.039 (6)	0.046 (6)	−0.005 (4)	−0.009 (4)	0.003 (5)
N4	0.033 (5)	0.040 (6)	0.034 (5)	0.006 (4)	0.000 (4)	−0.012 (5)
N5	0.029 (4)	0.041 (6)	0.019 (4)	0.004 (4)	−0.005 (3)	−0.003 (4)
N6	0.035 (5)	0.036 (6)	0.038 (5)	−0.010 (4)	−0.007 (4)	−0.008 (5)
C1	0.051 (7)	0.046 (8)	0.030 (6)	0.006 (6)	0.004 (5)	−0.003 (5)
C2	0.044 (7)	0.065 (9)	0.024 (6)	0.006 (6)	0.004 (5)	0.001 (6)
C3	0.047 (7)	0.037 (7)	0.029 (6)	0.013 (5)	−0.009 (5)	0.005 (5)
C4	0.036 (6)	0.037 (7)	0.037 (7)	0.005 (5)	−0.003 (5)	0.000 (6)
C5	0.030 (6)	0.036 (7)	0.025 (6)	0.000 (5)	−0.004 (4)	−0.003 (5)
C6	0.055 (7)	0.034 (7)	0.019 (5)	−0.003 (5)	−0.001 (5)	0.002 (5)
C7	0.042 (6)	0.038 (7)	0.022 (6)	−0.005 (5)	−0.004 (5)	−0.001 (5)
C8	0.044 (7)	0.047 (8)	0.034 (6)	−0.009 (6)	0.005 (5)	−0.007 (6)
C9	0.049 (7)	0.037 (7)	0.046 (8)	0.003 (6)	−0.017 (6)	−0.014 (6)
C10	0.040 (7)	0.052 (9)	0.054 (8)	0.018 (6)	−0.004 (6)	−0.007 (7)
C11	0.040 (7)	0.048 (8)	0.045 (7)	−0.006 (6)	−0.004 (5)	0.005 (6)
C12	0.037 (6)	0.031 (7)	0.053 (8)	0.006 (5)	−0.008 (5)	−0.005 (6)
C13	0.031 (6)	0.043 (8)	0.061 (8)	−0.003 (5)	0.008 (5)	−0.007 (6)
C14	0.036 (6)	0.047 (8)	0.037 (6)	−0.005 (5)	0.006 (5)	−0.009 (6)
C15	0.028 (5)	0.047 (8)	0.025 (6)	−0.001 (5)	−0.008 (4)	0.002 (5)
C16	0.025 (5)	0.039 (7)	0.030 (6)	−0.011 (5)	−0.005 (4)	−0.008 (5)
C17	0.020 (5)	0.048 (8)	0.031 (6)	−0.005 (5)	−0.006 (4)	0.013 (5)
C18	0.038 (6)	0.038 (7)	0.028 (6)	−0.008 (5)	−0.014 (5)	0.000 (5)
C19	0.042 (6)	0.055 (9)	0.030 (6)	−0.010 (6)	0.004 (5)	0.011 (6)
C20	0.043 (7)	0.052 (9)	0.035 (7)	−0.006 (6)	−0.008 (5)	0.008 (6)
C21	0.062 (8)	0.033 (8)	0.054 (8)	−0.008 (6)	−0.019 (6)	−0.002 (6)
C22	0.068 (8)	0.038 (8)	0.040 (7)	−0.010 (6)	0.004 (6)	−0.008 (6)

Geometric parameters (Å, º) top

I1—Cu1	2.5645 (16)	C5—H5A	0.9500
I2—Cu2	2.5832 (14)	C6—C7	1.443 (14)
Cu1—N4	1.980 (9)	C6—H6A	0.9500
Cu1—N3	2.074 (9)	C7—C8	1.365 (14)
Cu1—N2	2.078 (8)	C8—C9	1.372 (15)
Cu2—N1	2.018 (8)	C8—H8A	0.9500
Cu2—N6ⁱ	2.053 (9)	C9—C10	1.371 (15)
Cu2—N5ⁱ	2.107 (8)	C9—H9A	0.9500
N1—C5	1.350 (12)	C10—C11	1.382 (14)
N1—C1	1.361 (13)	C10—H10A	0.9500
N2—C6	1.291 (12)	C11—H11A	0.9500
N2—C4	1.445 (12)	C12—C13	1.415 (15)
N3—C11	1.341 (13)	C12—H12A	0.9500
N3—C7	1.362 (12)	C13—C14	1.362 (15)
N4—C12	1.323 (12)	C13—H13A	0.9500
N4—C16	1.372 (13)	C14—C15	1.390 (14)
N5—C17	1.270 (12)	C14—H14A	0.9500
N5—C15	1.426 (13)	C15—C16	1.381 (13)
N5—Cu2ⁱⁱ	2.107 (8)	C16—H16A	0.9500
N6—C22	1.347 (14)	C17—C18	1.439 (15)
N6—C18	1.376 (13)	C17—H17A	0.9500
N6—Cu2ⁱⁱ	2.053 (9)	C18—C19	1.382 (14)
C1—C2	1.376 (14)	C19—C20	1.366 (16)
C1—H1A	0.9500	C19—H19A	0.9500
C2—C3	1.386 (14)	C20—C21	1.413 (15)
C2—H2A	0.9500	C20—H20A	0.9500
C3—C4	1.358 (14)	C21—C22	1.382 (16)
C3—H3A	0.9500	C21—H21A	0.9500
C4—C5	1.339 (13)	C22—H22A	0.9500

N4—Cu1—N3	119.2 (4)	N3—C7—C8	122.0 (10)
N4—Cu1—N2	125.5 (3)	N3—C7—C6	114.4 (9)
N3—Cu1—N2	80.4 (3)	C8—C7—C6	123.5 (10)
N4—Cu1—I1	105.3 (3)	C7—C8—C9	120.7 (11)
N3—Cu1—I1	112.1 (2)	C7—C8—H8A	119.6
N2—Cu1—I1	112.9 (2)	C9—C8—H8A	119.6
N1—Cu2—N6ⁱ	126.9 (3)	C10—C9—C8	118.5 (11)
N1—Cu2—N5ⁱ	113.9 (3)	C10—C9—H9A	120.8
N6ⁱ—Cu2—N5ⁱ	79.8 (3)	C8—C9—H9A	120.8
N1—Cu2—I2	109.9 (2)	C9—C10—C11	118.2 (11)
N6ⁱ—Cu2—I2	106.7 (2)	C9—C10—H10A	120.9
N5ⁱ—Cu2—I2	117.3 (2)	C11—C10—H10A	120.9
C5—N1—C1	118.5 (9)	N3—C11—C10	124.3 (11)
C5—N1—Cu2	121.7 (7)	N3—C11—H11A	117.8
C1—N1—Cu2	119.7 (7)	C10—C11—H11A	117.8
C6—N2—C4	122.4 (9)	N4—C12—C13	123.7 (11)
C6—N2—Cu1	111.2 (7)	N4—C12—H12A	118.2
C4—N2—Cu1	126.4 (6)	C13—C12—H12A	118.2
C11—N3—C7	116.3 (9)	C14—C13—C12	119.0 (10)
C11—N3—Cu1	131.4 (8)	C14—C13—H13A	120.5
C7—N3—Cu1	112.3 (7)	C12—C13—H13A	120.5
C12—N4—C16	116.4 (9)	C13—C14—C15	118.5 (10)
C12—N4—Cu1	122.0 (8)	C13—C14—H14A	120.8
C16—N4—Cu1	120.5 (6)	C15—C14—H14A	120.8
C17—N5—C15	121.6 (9)	C16—C15—C14	119.4 (11)
C17—N5—Cu2ⁱⁱ	111.3 (7)	C16—C15—N5	114.6 (9)
C15—N5—Cu2ⁱⁱ	126.8 (6)	C14—C15—N5	125.9 (9)
C22—N6—C18	117.7 (9)	N4—C16—C15	122.9 (9)
C22—N6—Cu2ⁱⁱ	128.6 (7)	N4—C16—H16A	118.5
C18—N6—Cu2ⁱⁱ	113.1 (7)	C15—C16—H16A	118.5
N1—C1—C2	121.3 (10)	N5—C17—C18	121.6 (10)
N1—C1—H1A	119.3	N5—C17—H17A	119.2
C2—C1—H1A	119.3	C18—C17—H17A	119.2
C1—C2—C3	118.2 (10)	N6—C18—C19	121.5 (10)
C1—C2—H2A	120.9	N6—C18—C17	113.8 (9)
C3—C2—H2A	120.9	C19—C18—C17	124.7 (10)
C4—C3—C2	119.5 (10)	C20—C19—C18	121.5 (11)
C4—C3—H3A	120.2	C20—C19—H19A	119.3
C2—C3—H3A	120.2	C18—C19—H19A	119.3
C5—C4—C3	120.5 (10)	C19—C20—C21	116.8 (11)
C5—C4—N2	124.3 (9)	C19—C20—H20A	121.6
C3—C4—N2	115.2 (9)	C21—C20—H20A	121.6
C4—C5—N1	121.8 (9)	C22—C21—C20	120.1 (11)
C4—C5—H5A	119.1	C22—C21—H21A	119.9
N1—C5—H5A	119.1	C20—C21—H21A	119.9
N2—C6—C7	121.3 (9)	N6—C22—C21	122.4 (11)
N2—C6—H6A	119.4	N6—C22—H22A	118.8
C7—C6—H6A	119.4	C21—C22—H22A	118.8

Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+5/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···I1ⁱⁱⁱ	0.95	3.03	3.789 (12)	138
C20—H20A···I1^iv	0.95	3.14	4.025 (12)	156
C17—H17A···I2^v	0.95	3.16	4.011 (11)	149

Symmetry codes: (iii) x, y−1, z; (iv) −x+3, −y−1, −z+1; (v) x+1/2, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[CuI(C₁₁H₉N₃)]·0.5C₂H₃N
M_r	394.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	7.1800 (2), 13.2303 (7), 27.9383 (13)
β (°)	90.741 (3)
V (Å³)	2653.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.96
Crystal size (mm)	0.17 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.569, 0.733
No. of measured, independent and observed [I > 2σ(I)] reflections	19063, 4676, 2627
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.178, 1.02
No. of reflections	4676
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.39, −1.24

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···I1ⁱ	0.95	3.03	3.789 (12)	138
C20—H20A···I1ⁱⁱ	0.95	3.14	4.025 (12)	156
C17—H17A···I2ⁱⁱⁱ	0.95	3.16	4.011 (11)	149

Symmetry codes: (i) x, y−1, z; (ii) −x+3, −y−1, −z+1; (iii) x+1/2, −y−1/2, z+1/2.

Acknowledgements

The authors are grateful to the Islamic Azad University, University Research Councils for partial support of this work. The crystal structure analysis was carried out by Dr A. J. Lough of the Department of Chemistry of the University of Toronto, Canada.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dehghanpour, S., Khalaj, M. & Mahmoudi, A. (2009). Polyhedron, 28, 1205–1210. Web of Science CSD CrossRef CAS Google Scholar
Fei, B. L., Sun, W. Y., Yu, K. B. & Tang, W. X. (2000). J. Chem. Soc. Dalton Trans. pp. 805–811. Web of Science CSD CrossRef Google Scholar
Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629–1658. Web of Science CrossRef PubMed CAS Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.