catena-Poly[[[(1,10-phenanthroline)copper(I)]-μ-cyanido] ethanol hemisolvate]

Nie, J.; Wang, J.; Dai, C.

doi:10.1107/S1600536810045186

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages m1538-m1539

https://doi.org/10.1107/S1600536810045186

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catena-Poly[[[(1,10-phenanthroline)copper(I)]-μ-cyanido] ethanol hemisolvate]

Jianhua Nie,^a Jun Wang ^a and Chuntao Dai ^a ^*

^aZhongshan Polytechnic, Zhongshan, Guangdong 528404, People's Republic of China
^*Correspondence e-mail: wangjun7203@126.com

(Received 3 November 2010; accepted 4 November 2010; online 10 November 2010)

In the title coordination polymer, {[Cu(CN)(C₁₂H₁₀N₂)]·0.5C₂H₅OH}_n, there are two Cu^I ions, two 1,10-phenanthroline (phen) ligands and two cyanide ions in the asymmetric unit along with a highly disordered ethanol solvent molecule, which was modelled as being disordered over two sets of sites in a 0.829 (7):0.171 (7) ratio. The orientation/ordering of the C and N atoms of the cyanide ions could not be determined in the present refinement and they were modelled as being statistically disordered. Both copper ions are coordinated by an N,N′-bidentate phen ligand and two cyanide ligands, generating distorted tetrahedral CuN₂Q₂ (Q = C or N) tetrahedra. The μ-cyanide ligands link the metal ions, forming a zigzag chain propagating in [001]. The chains are cross-linked by numerous aromatic π–π stacking contacts between adjacent phen rings [minimum centroid–centroid separation = 3.620 (3) Å].

Related literature

For general background to cyanide coordination polymers, see: Holmes & Girolami (1999 ); Deng et al. (2008 ). For related structures, see: Dyason et al. (1985 ); Chesnut et al. (1999 ); Zhao et al. (2004 ); Huang et al. (2004 ).

Experimental

Crystal data

[Cu(CN)(C₁₂H₁₀N₂)]·0.5C₂H₆O
M_r = 292.8
Monoclinic, P 2₁ /c
a = 18.4896 (6) Å
b = 8.4033 (3) Å
c = 16.5166 (5) Å
β = 109.974 (2)°
V = 2411.88 (14) Å³
Z = 8
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.662, T_max = 0.726
21068 measured reflections
4729 independent reflections
2624 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.159
S = 1.02
4729 reflections
344 parameters
65 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—C1/N1	1.910 (6)
Cu1—C2′/N2′	1.944 (6)
Cu1—N4	2.108 (5)
Cu1—N3	2.142 (4)
Cu2—C2ⁱ/N2ⁱ	1.909 (6)
Cu2—C1′/N1′	1.921 (5)
Cu2—N6	2.126 (5)
Cu2—N5	2.130 (4)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810045186/hb5723sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045186/hb5723Isup2.hkl

checkCIF report

Comment top

Metal coordination polymer based on cyanide group have raised intense interest due to their structural diversity and their potential applications in magnetic materials (Holmes & Girolami, 1999; Deng et al., 2008). Up to date, a large number of one-, two-, and three-dimensional coordination polymers have been prepared by the choice of metal-cyanide bridging centers and versatile secondary ligands such as 1,10-phenanthroline and 2,2-pyridine (Dyason et al., 1985; Chesnut et al., 1999; Zhao et al., 2004; Huang et al., 2004). Herein, we obtained one copper coordination polymer of [Cu(C₁₂H₁₀N₂)(CN).C₂H₆O]_n under hydrothermal condition, and its structure was reported.

As depicted in Fig. 1, each Cuⁱ ion is four-coordianted by two N atoms from one 1,10-phenanthroline (phen) ligand and two cyano ligands. The Cu-phen subunits are in turn interconnected by /m₂-cyano ligands to form a 1D zigzag chain. These chains are further assembled by /p···/p stacking contacts between adjacent phen rings and extend to form a three-dimensional supramolecular network (Fig. 2). The interplanar distance between them is ca. 3.60 Å (symmetry operator for the 1,10-phenanthroline ligand: 1-x, 1-y, 2-z). The lattice ethanol molecule is independently disordered over two parts of 0.829 (7): 0.171 (7). (see refinement section for details).

Related literature top

For general background to cyanide coordination polymers, see: Holmes & Girolami (1999); Deng et al. (2008). For related structures, see: Dyason et al. (1985); Chesnut et al. (1999); Zhao et al. (2004); Huang et al. (2004).

Experimental top

Copper(I) cyanide (0.089 g, 1 mmol) and 1,10-phenanthroline (0.1801 g, 1 mmol) were added to a mixture of water (5 ml) and ethanol (5 ml). The resultant mixture was sealed in a 20 ml stainless steel reactor with a Teflon liner and kept under autogenous pressure at 413 K for 48 h, and then cooled to room temperature at a rate of 5 K/min. Yellow blocks of (I) formed with a yield of approximately 58% based on 1,10-phenanthroline.

Structure description top

For general background to cyanide coordination polymers, see: Holmes & Girolami (1999); Deng et al. (2008). For related structures, see: Dyason et al. (1985); Chesnut et al. (1999); Zhao et al. (2004); Huang et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP represention of (I), showing 30% probability displacement ellipsoids. Symmetry codes: (a) x, 1.5-y, 0.5+z.
	Fig. 2. View of the three-dimensional structure of the title compound.

catena-Poly[[[(1,10-phenanthroline)copper(I)]-µ-cyanido] ethanol hemisolvate] top

Crystal data top

[Cu(CN)(C₁₂H₁₀N₂)]·0.5C₂H₆O	F(000) = 1192
M_r = 292.8	D_x = 1.613 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4800 reflections
a = 18.4896 (6) Å	θ = 1.4–28.0°
b = 8.4033 (3) Å	µ = 1.80 mm⁻¹
c = 16.5166 (5) Å	T = 293 K
β = 109.974 (2)°	Block, yellow
V = 2411.88 (14) Å³	0.25 × 0.23 × 0.19 mm
Z = 8

Data collection top

Bruker APEXII area-detector diffractometer	4729 independent reflections
Radiation source: fine-focus sealed tube	2624 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
φ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −22→22
T_min = 0.662, T_max = 0.726	k = −9→10
21068 measured reflections	l = −20→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0686P)² + 1.9113P] where P = (F_o² + 2F_c²)/3
4729 reflections	(Δ/σ)_max = 0.004
344 parameters	Δρ_max = 0.37 e Å⁻³
65 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Cu(CN)(C₁₂H₁₀N₂)]·0.5C₂H₆O	V = 2411.88 (14) Å³
M_r = 292.8	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.4896 (6) Å	µ = 1.80 mm⁻¹
b = 8.4033 (3) Å	T = 293 K
c = 16.5166 (5) Å	0.25 × 0.23 × 0.19 mm
β = 109.974 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	4729 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2624 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.726	R_int = 0.090
21068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	65 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
4729 reflections	Δρ_min = −0.53 e Å⁻³
344 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.19744 (4)	0.57901 (10)	0.46043 (5)	0.0533 (3)
Cu2	0.32714 (4)	0.65348 (10)	0.77685 (4)	0.0523 (3)
C1	0.2519 (3)	0.5967 (7)	0.5813 (4)	0.0557 (15)	0.50
N1'	0.2519 (3)	0.5967 (7)	0.5813 (4)	0.0557 (15)	0.50
C2	0.2732 (3)	0.7392 (7)	0.3409 (3)	0.0470 (13)	0.50
N2'	0.2732 (3)	0.7392 (7)	0.3409 (3)	0.0470 (13)	0.50
N1	0.2828 (3)	0.6179 (7)	0.6549 (3)	0.0501 (14)	0.50
C1'	0.2828 (3)	0.6179 (7)	0.6549 (3)	0.0501 (14)	0.50
N2	0.2420 (3)	0.6744 (7)	0.3810 (3)	0.0477 (14)	0.50
C2'	0.2420 (3)	0.6744 (7)	0.3810 (3)	0.0477 (14)	0.50
C3	0.0414 (4)	0.7502 (8)	0.4464 (4)	0.0511 (16)
H3	0.0709	0.8383	0.4719	0.061*
C4	−0.0382 (4)	0.7600 (9)	0.4252 (4)	0.0624 (18)
H4	−0.0610	0.8524	0.4363	0.075*
C5	−0.0817 (4)	0.6332 (10)	0.3883 (4)	0.0644 (19)
H5	−0.1349	0.6380	0.3736	0.077*
C6	−0.0470 (3)	0.4939 (8)	0.3722 (3)	0.0472 (15)
C7	−0.0889 (4)	0.3551 (10)	0.3317 (4)	0.0605 (19)
H7	−0.1423	0.3555	0.3143	0.073*
C8	−0.0529 (4)	0.2249 (9)	0.3185 (4)	0.0594 (18)
H8	−0.0818	0.1375	0.2911	0.071*
C9	0.0284 (4)	0.2175 (8)	0.3455 (3)	0.0491 (15)
C10	0.0687 (4)	0.0835 (9)	0.3361 (4)	0.0640 (19)
H10	0.0424	−0.0067	0.3086	0.077*
C11	0.1467 (5)	0.0854 (9)	0.3675 (5)	0.071 (2)
H11	0.1741	−0.0056	0.3639	0.085*
C12	0.1861 (4)	0.2228 (9)	0.4050 (4)	0.0619 (18)
H12	0.2396	0.2219	0.4249	0.074*
C13	0.0718 (3)	0.3522 (7)	0.3842 (3)	0.0390 (13)
C14	0.0331 (3)	0.4941 (7)	0.3959 (3)	0.0397 (13)
C15	0.4760 (4)	0.8556 (8)	0.8029 (4)	0.0519 (16)
H15	0.4437	0.9339	0.7698	0.062*
C16	0.5546 (4)	0.8874 (9)	0.8372 (4)	0.0601 (18)
H16	0.5737	0.9853	0.8276	0.072*
C17	0.6029 (3)	0.7741 (9)	0.8847 (4)	0.0586 (18)
H17	0.6554	0.7944	0.9081	0.070*
C18	0.5739 (3)	0.6280 (8)	0.8983 (4)	0.0513 (17)
C19	0.6205 (4)	0.5004 (10)	0.9452 (4)	0.0663 (19)
H19	0.6735	0.5141	0.9693	0.080*
C20	0.5893 (4)	0.3616 (10)	0.9550 (4)	0.070 (2)
H20	0.6211	0.2808	0.9862	0.084*
C21	0.5079 (4)	0.3337 (8)	0.9189 (4)	0.0519 (16)
C22	0.4723 (5)	0.1913 (10)	0.9253 (5)	0.074 (2)
H22	0.5018	0.1072	0.9559	0.089*
C23	0.3964 (5)	0.1732 (9)	0.8881 (5)	0.078 (2)
H23	0.3729	0.0772	0.8924	0.094*
C24	0.3532 (4)	0.2993 (9)	0.8432 (4)	0.0617 (18)
H24	0.3005	0.2848	0.8168	0.074*
C25	0.4607 (3)	0.4565 (7)	0.8732 (3)	0.0419 (14)
C26	0.4937 (3)	0.6066 (7)	0.8619 (3)	0.0390 (14)
N3	0.0772 (2)	0.6226 (6)	0.4324 (3)	0.0404 (12)
N4	0.1499 (3)	0.3554 (6)	0.4134 (3)	0.0466 (12)
N5	0.4451 (2)	0.7205 (6)	0.8149 (3)	0.0392 (11)
N6	0.3829 (3)	0.4406 (6)	0.8355 (3)	0.0424 (12)
C27	0.1951 (6)	0.5287 (13)	0.0858 (7)	0.100 (4)	0.829 (7)
H27A	0.2274	0.5476	0.0520	0.150*	0.829 (7)
H27B	0.1758	0.6283	0.0984	0.150*	0.829 (7)
H27C	0.1528	0.4620	0.0541	0.150*	0.829 (7)
C28	0.2396 (8)	0.450 (4)	0.1658 (10)	0.112 (6)	0.829 (7)
H28A	0.2562	0.3474	0.1522	0.135*	0.829 (7)
H28B	0.2853	0.5131	0.1940	0.135*	0.829 (7)
O1	0.2007 (8)	0.4284 (18)	0.2226 (10)	0.274 (9)	0.829 (7)
H1	0.1873	0.5150	0.2355	0.411*	0.829 (7)
C27'	0.230 (3)	0.475 (17)	0.147 (6)	0.100 (4)	0.171 (7)
H27D	0.2071	0.3846	0.1122	0.150*	0.171 (7)
H27E	0.1988	0.5674	0.1261	0.150*	0.171 (7)
H27F	0.2345	0.4553	0.2057	0.150*	0.171 (7)
C28'	0.309 (3)	0.503 (8)	0.142 (3)	0.112 (6)	0.171 (7)
H28C	0.3146	0.4410	0.0951	0.135*	0.171 (7)
H28D	0.3145	0.6143	0.1304	0.135*	0.171 (7)
O1'	0.367 (3)	0.459 (8)	0.220 (4)	0.274 (9)	0.171 (7)
H1'	0.3630	0.3649	0.2298	0.411*	0.171 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0405 (4)	0.0661 (6)	0.0510 (4)	−0.0090 (4)	0.0126 (3)	−0.0044 (4)
Cu2	0.0375 (4)	0.0655 (6)	0.0503 (4)	0.0059 (4)	0.0103 (3)	−0.0013 (4)
C1	0.038 (3)	0.074 (4)	0.053 (3)	0.005 (3)	0.013 (3)	0.002 (3)
N1'	0.038 (3)	0.074 (4)	0.053 (3)	0.005 (3)	0.013 (3)	0.002 (3)
C2	0.039 (3)	0.054 (4)	0.044 (3)	−0.001 (3)	0.009 (2)	−0.001 (3)
N2'	0.039 (3)	0.054 (4)	0.044 (3)	−0.001 (3)	0.009 (2)	−0.001 (3)
C3	0.064 (4)	0.041 (4)	0.049 (3)	0.002 (3)	0.020 (3)	0.003 (3)
C4	0.063 (5)	0.054 (5)	0.071 (4)	0.021 (4)	0.024 (4)	0.008 (4)
C5	0.042 (4)	0.082 (6)	0.069 (4)	0.012 (4)	0.019 (3)	0.014 (4)
C6	0.037 (3)	0.059 (4)	0.044 (3)	−0.003 (3)	0.012 (2)	0.009 (3)
C7	0.036 (3)	0.086 (6)	0.055 (4)	−0.017 (4)	0.011 (3)	0.008 (4)
C8	0.056 (4)	0.063 (5)	0.057 (4)	−0.020 (4)	0.016 (3)	−0.008 (4)
C9	0.061 (4)	0.047 (4)	0.045 (3)	−0.009 (3)	0.025 (3)	−0.004 (3)
C10	0.086 (6)	0.056 (5)	0.056 (4)	−0.009 (4)	0.031 (4)	−0.008 (3)
C11	0.094 (6)	0.050 (5)	0.076 (5)	0.017 (4)	0.038 (4)	−0.001 (4)
C12	0.062 (4)	0.061 (5)	0.063 (4)	0.018 (4)	0.022 (3)	0.003 (4)
C13	0.042 (3)	0.043 (4)	0.035 (3)	−0.001 (3)	0.017 (2)	0.001 (3)
C14	0.038 (3)	0.046 (4)	0.035 (3)	−0.001 (3)	0.012 (2)	0.003 (3)
C15	0.055 (4)	0.053 (4)	0.049 (3)	−0.007 (3)	0.019 (3)	0.004 (3)
C16	0.059 (4)	0.067 (5)	0.064 (4)	−0.022 (4)	0.033 (3)	−0.001 (4)
C17	0.036 (3)	0.080 (5)	0.060 (4)	−0.017 (4)	0.015 (3)	−0.008 (4)
C18	0.032 (3)	0.072 (5)	0.048 (3)	0.001 (3)	0.011 (3)	−0.005 (3)
C19	0.039 (4)	0.084 (6)	0.061 (4)	0.010 (4)	−0.002 (3)	0.003 (4)
C20	0.060 (5)	0.087 (6)	0.052 (4)	0.034 (4)	0.004 (3)	0.011 (4)
C21	0.069 (4)	0.041 (4)	0.046 (3)	0.014 (3)	0.019 (3)	0.003 (3)
C22	0.097 (6)	0.059 (6)	0.068 (4)	0.021 (5)	0.031 (4)	0.009 (4)
C23	0.110 (7)	0.045 (5)	0.094 (6)	−0.010 (5)	0.053 (5)	0.009 (4)
C24	0.065 (4)	0.061 (5)	0.064 (4)	−0.021 (4)	0.029 (3)	−0.010 (4)
C25	0.041 (3)	0.052 (4)	0.032 (3)	0.005 (3)	0.011 (2)	−0.006 (3)
C26	0.036 (3)	0.048 (4)	0.033 (3)	−0.002 (3)	0.011 (2)	−0.008 (3)
N1	0.033 (3)	0.064 (4)	0.052 (3)	0.010 (3)	0.013 (2)	−0.009 (3)
C1'	0.033 (3)	0.064 (4)	0.052 (3)	0.010 (3)	0.013 (2)	−0.009 (3)
N2	0.036 (3)	0.060 (4)	0.044 (3)	−0.003 (3)	0.011 (2)	−0.001 (3)
C2'	0.036 (3)	0.060 (4)	0.044 (3)	−0.003 (3)	0.011 (2)	−0.001 (3)
N3	0.041 (3)	0.041 (3)	0.038 (2)	0.000 (2)	0.013 (2)	0.000 (2)
N4	0.040 (3)	0.058 (4)	0.042 (2)	0.010 (3)	0.015 (2)	−0.002 (2)
N5	0.039 (3)	0.041 (3)	0.036 (2)	0.003 (2)	0.011 (2)	0.000 (2)
N6	0.047 (3)	0.044 (3)	0.041 (2)	−0.006 (2)	0.020 (2)	−0.004 (2)
C27	0.084 (8)	0.078 (8)	0.118 (9)	−0.019 (6)	0.008 (6)	−0.006 (7)
C28	0.100 (10)	0.134 (17)	0.119 (13)	−0.017 (9)	0.058 (9)	−0.018 (11)
O1	0.205 (14)	0.190 (14)	0.35 (2)	0.042 (11)	0.002 (13)	−0.103 (14)
C27'	0.084 (8)	0.078 (8)	0.118 (9)	−0.019 (6)	0.008 (6)	−0.006 (7)
C28'	0.100 (10)	0.134 (17)	0.119 (13)	−0.017 (9)	0.058 (9)	−0.018 (11)
O1'	0.205 (14)	0.190 (14)	0.35 (2)	0.042 (11)	0.002 (13)	−0.103 (14)

Geometric parameters (Å, º) top

Cu1—C1	1.910 (6)	C15—C16	1.393 (8)
Cu1—N1'	1.910 (6)	C15—H15	0.9300
Cu1—N2	1.944 (6)	C16—C17	1.357 (9)
Cu1—C2'	1.944 (6)	C16—H16	0.9300
Cu1—N4	2.108 (5)	C17—C18	1.389 (9)
Cu1—N3	2.142 (4)	C17—H17	0.9300
Cu2—N2'ⁱ	1.909 (6)	C18—C26	1.409 (7)
Cu2—C2ⁱ	1.909 (6)	C18—C19	1.427 (9)
Cu2—N1	1.921 (5)	C19—C20	1.336 (10)
Cu2—C1'	1.921 (5)	C19—H19	0.9300
Cu2—N6	2.126 (5)	C20—C21	1.435 (9)
Cu2—N5	2.130 (4)	C20—H20	0.9300
C1—N1	1.167 (7)	C21—C22	1.387 (10)
C2—N2	1.154 (6)	C21—C25	1.395 (8)
C2—Cu2ⁱⁱ	1.909 (6)	C22—C23	1.335 (10)
C3—N3	1.322 (7)	C22—H22	0.9300
C3—C4	1.395 (9)	C23—C24	1.380 (10)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.348 (9)	C24—N6	1.332 (8)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.405 (9)	C25—N6	1.365 (7)
C5—H5	0.9300	C25—C26	1.441 (8)
C6—C14	1.395 (7)	C26—N5	1.358 (7)
C6—C7	1.433 (9)	C27—C28	1.454 (9)
C7—C8	1.337 (9)	C27—H27A	0.9600
C7—H7	0.9300	C27—H27B	0.9600
C8—C9	1.416 (8)	C27—H27C	0.9600
C8—H8	0.9300	C28—O1	1.375 (9)
C9—C10	1.387 (9)	C28—H28A	0.9700
C9—C13	1.408 (8)	C28—H28B	0.9700
C10—C11	1.356 (9)	O1—H1	0.8200
C10—H10	0.9300	C27'—C28'	1.503 (10)
C11—C12	1.393 (10)	C27'—H27D	0.9600
C11—H11	0.9300	C27'—H27E	0.9600
C12—N4	1.331 (8)	C27'—H27F	0.9600
C12—H12	0.9300	C28'—O1'	1.415 (10)
C13—N4	1.357 (7)	C28'—H28C	0.9700
C13—C14	1.437 (8)	C28'—H28D	0.9700
C14—N3	1.363 (7)	O1'—H1'	0.8200
C15—N5	1.316 (7)

C1—Cu1—N2	118.7 (2)	C20—C19—H19	119.4
C1—Cu1—N4	117.3 (2)	C18—C19—H19	119.4
N2—Cu1—N4	109.8 (2)	C19—C20—C21	121.8 (6)
C1—Cu1—N3	110.49 (19)	C19—C20—H20	119.1
N2—Cu1—N3	115.55 (19)	C21—C20—H20	119.1
N4—Cu1—N3	78.53 (18)	C22—C21—C25	116.9 (6)
C2ⁱ—Cu2—N1	122.6 (2)	C22—C21—C20	124.5 (7)
C2ⁱ—Cu2—N6	114.1 (2)	C25—C21—C20	118.6 (6)
N1—Cu2—N6	108.3 (2)	C23—C22—C21	121.0 (7)
C2ⁱ—Cu2—N5	112.80 (19)	C23—C22—H22	119.5
N1—Cu2—N5	112.18 (19)	C21—C22—H22	119.5
N6—Cu2—N5	78.45 (18)	C22—C23—C24	118.9 (7)
N1—C1—Cu1	175.2 (5)	C22—C23—H23	120.5
N2—C2—Cu2ⁱⁱ	178.6 (5)	C24—C23—H23	120.5
N3—C3—C4	123.5 (6)	N6—C24—C23	123.6 (7)
N3—C3—H3	118.2	N6—C24—H24	118.2
C4—C3—H3	118.2	C23—C24—H24	118.2
C5—C4—C3	118.9 (6)	N6—C25—C21	122.8 (6)
C5—C4—H4	120.6	N6—C25—C26	117.0 (5)
C3—C4—H4	120.6	C21—C25—C26	120.2 (5)
C4—C5—C6	120.2 (6)	N5—C26—C18	123.2 (6)
C4—C5—H5	119.9	N5—C26—C25	117.7 (5)
C6—C5—H5	119.9	C18—C26—C25	119.1 (5)
C14—C6—C5	117.1 (6)	C1—N1—Cu2	176.2 (5)
C14—C6—C7	119.0 (6)	C2—N2—Cu1	173.2 (5)
C5—C6—C7	123.9 (6)	C3—N3—C14	117.4 (5)
C8—C7—C6	121.4 (6)	C3—N3—Cu1	130.2 (4)
C8—C7—H7	119.3	C14—N3—Cu1	112.3 (4)
C6—C7—H7	119.3	C12—N4—C13	117.3 (6)
C7—C8—C9	121.3 (6)	C12—N4—Cu1	128.5 (4)
C7—C8—H8	119.4	C13—N4—Cu1	114.1 (4)
C9—C8—H8	119.4	C15—N5—C26	117.3 (5)
C10—C9—C13	117.4 (6)	C15—N5—Cu2	129.6 (4)
C10—C9—C8	123.6 (6)	C26—N5—Cu2	113.1 (4)
C13—C9—C8	119.1 (6)	C24—N6—C25	116.6 (5)
C11—C10—C9	119.3 (7)	C24—N6—Cu2	130.0 (4)
C11—C10—H10	120.4	C25—N6—Cu2	113.4 (4)
C9—C10—H10	120.4	C28—C27—H27A	109.5
C10—C11—C12	120.4 (7)	C28—C27—H27B	109.5
C10—C11—H11	119.8	H27A—C27—H27B	109.5
C12—C11—H11	119.8	C28—C27—H27C	109.5
N4—C12—C11	122.3 (6)	H27A—C27—H27C	109.5
N4—C12—H12	118.8	H27B—C27—H27C	109.5
C11—C12—H12	118.8	O1—C28—C27	114.6 (13)
N4—C13—C9	123.3 (6)	O1—C28—H28A	108.6
N4—C13—C14	117.0 (5)	C27—C28—H28A	108.6
C9—C13—C14	119.7 (5)	O1—C28—H28B	108.6
N3—C14—C6	122.8 (6)	C27—C28—H28B	108.6
N3—C14—C13	117.8 (5)	H28A—C28—H28B	107.6
C6—C14—C13	119.3 (5)	C28—O1—H1	109.5
N5—C15—C16	123.3 (6)	C28'—C27'—H27D	109.5
N5—C15—H15	118.3	C28'—C27'—H27E	109.5
C16—C15—H15	118.3	H27D—C27'—H27E	109.5
C17—C16—C15	119.4 (6)	C28'—C27'—H27F	109.5
C17—C16—H16	120.3	H27D—C27'—H27F	109.5
C15—C16—H16	120.3	H27E—C27'—H27F	109.5
C16—C17—C18	119.9 (6)	O1'—C28'—C27'	111.5 (16)
C16—C17—H17	120.0	O1'—C28'—H28C	109.3
C18—C17—H17	120.0	C27'—C28'—H28C	109.3
C17—C18—C26	116.9 (6)	O1'—C28'—H28D	109.3
C17—C18—C19	123.9 (6)	C27'—C28'—H28D	109.3
C26—C18—C19	119.2 (6)	H28C—C28'—H28D	108.0
C20—C19—C18	121.1 (6)	C28'—O1'—H1'	109.5

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

Experimental details

Crystal data
Chemical formula	[Cu(CN)(C₁₂H₁₀N₂)]·0.5C₂H₆O
M_r	292.8
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	18.4896 (6), 8.4033 (3), 16.5166 (5)
β (°)	109.974 (2)
V (Å³)	2411.88 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
Crystal size (mm)	0.25 × 0.23 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.662, 0.726
No. of measured, independent and observed [I > 2σ(I)] reflections	21068, 4729, 2624
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.159, 1.02
No. of reflections	4729
No. of parameters	344
No. of restraints	65
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.53

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—C1	1.910 (6)	Cu2—C2ⁱ	1.909 (6)
Cu1—C2'	1.944 (6)	Cu2—C1'	1.921 (5)
Cu1—N4	2.108 (5)	Cu2—N6	2.126 (5)
Cu1—N3	2.142 (4)	Cu2—N5	2.130 (4)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

The authors acknowledge Zhongshan Polytechnic for supporting this work.

References

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