catena-Poly[[(1,10-phenanthroline-κ2N,N′)copper(I)]-μ-thiocyanato-κ2N:S-[(1,10-phenanthroline-κ2N,N′)copper(I)]-μ-cyanido-κ2N:C]

Zhao, J.; Dong, W.-W.; Li, D.-S.; Ke, X.-J.

doi:10.1107/S1600536808037744

catena-Poly[[(1,10-phenanthroline-κ²N,N′)copper(I)]-μ-thiocyanato-κ²N:S-[(1,10-phenanthroline-κ²N,N′)copper(I)]-μ-cyanido-κ²N:C]

J. Zhao, W.-W. Dong, D.-S. Li and X.-J. Ke

In the title complex, [Cu₂(CN)(NCS)(C₁₂H₈N₂)₂], which was synthesized under hydrothermal conditions, both Cu^I atoms have a slightly distorted tetrahedral geometry. They are coordinated by two N atoms of one 1,10-phenanthroline ligand, one bridging thiocyanate anion and one bridging cyanide anion. In the crystal structure, infinite helical {Cu–CN–Cu–SCN}_n chains are formed along [ ${\overline 1}$ 01].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037744/bt2813sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037744/bt2813Isup2.hkl Contains datablock I

CCDC reference: 712322

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.061
wR factor = 0.164
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   293.000
            Value of melting point given =     0.000
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.45
           From the CIF: _diffrn_reflns_theta_full          27.45
           From the CIF: _reflns_number_total               4959
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5433
           Completeness (_total/calc)             91.28%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.91
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     --  C1      ..       5.63 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    --  S1_a    ..       8.19 su
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        700 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C3     --  C4      ..       0.10  Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C16    --  C17     ..       0.11  Ang.

Alert level G
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C6     -C14           1.42 Ang.
PLAT333_ALERT_2_G Check Large Av C6-Ring C-C Dist. C18    -C26           1.41 Ang.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -CU2 -C1  -N1   -122.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N6  -CU2 -C1  -N1    107.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N5  -CU2 -C1  -N1     11.00 11.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            C1  -CU2 -N2  -C2     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N6  -CU2 -N2  -C2    -41.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N5  -CU2 -N2  -C2     40.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            CU2 -C1  -N1  -CU1   -39.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            N3  -CU1 -N1  -C1   -177.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            N4  -CU1 -N1  -C1     85.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            S1  -CU1 -N1  -C1    -49.00  2.00   4.576   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         35
            CU2 -N2  -C2  -S1    -66.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        110
            N2  -C2  -S1  -CU1   163.00  6.00   1.555   1.555   1.555   4.675

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
  16 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Self-assembly processes that lead to helical structures are common throughout biology and chemistry (Luan et al., 2006; Piguet et al., 2005). Protein α-helices and the DNA double helix are well known biological examples which have inspired the work of synthetic chemists aiming to create chemical analogs of these complex structures (Greig et al., 2001). However, there is a little known about meso-helical self-assembling systems within this very active field of helical structure research in supramolecular chemistry (Cheng et al., 2006).

The crystal structure of the title complex contains two 1,10-Phen ligands, one CuSCN and one CuCN co-existing in the asymmetric unit, as illustrated in Fig. 1. The coordianation geometry of the four-coordinated Cu(1) is slightly distorted tetrahedral with two N donors of the chelating 1,10-Phen and another N donor [N(1)] of the CN^- occupying the basal sites and a S donor of SCN^- occupying the vertex site. The Cu(2) also has a slightly distorted tetrahedral geometry and is coordinated by two N atoms of one 1,10-Phen ligand, one bridging thiocyanate anion N atom [N(2)] and one bridging cyanide C atom [C(1)]. It is noteworthy that the Cu(I)atoms are linked by CN^- and SCN^- anions into infinite helical {CuCN-CuSCN}_n chains along a 2₁ screw axis, furthermore, the Cu₂(CN)(SCN) chains run around and cross two parallel axes forming meso-helices as showed in Fig. 2.

Related literature top

For related literature, see: Cheng, et al. (2006); Greig & Philp (2001); Luan et al. (2006); Piguet et al. (2005).

Experimental top

All chemicals were of reagent grade quality obtained from commercial sources and used without further purification. A mixture of CuSCN (0.60 mmol, 0.07 g), NaCN (1 mmol, 0.05 g),1,10-Phen (0.40 mmol, 0.07 g) and water (10 ml) in a 25 ml Teflon-lined stainless steel reactor was heated from 298 to 453 K in 2 h and maintained at 453 K for 72 h. After the mixture wascooled to 298 K, red crystals of the title compound were obtained (yield 43%).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The structure of the title compound, with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.
	Fig. 2. Left: presentation of the location of the copper centres of coordination polymer; Right: View of the meso-helical arrangement.

catena-Poly[[(1,10-phenanthroline-κ²N,N')copper(I)]-µ-thiocyanato-κ²N:S- [(1,10-phenanthroline-κ²N,N')copper(I)]-µ-cyanido-κ²N:C] top

Crystal data top

[Cu₂(CN)(NCS)(C₁₂H₈N₂)₂]	F(000) = 1152
M_r = 571.59	D_x = 1.596 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2103 reflections
a = 13.046 (7) Å	θ = 2.2–27.5°
b = 13.470 (7) Å	µ = 1.90 mm⁻¹
c = 13.538 (7) Å	T = 293 K
β = 90.044 (9)°	Prism, red
V = 2379 (2) Å³	0.30 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4959 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
CCD Profile fitting scans	h = −15→16
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	k = −17→15
T_min = 0.599, T_max = 0.804	l = −17→17
15496 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0669P)² + 0.4979P] where P = (F_o² + 2F_c²)/3
4959 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Cu₂(CN)(NCS)(C₁₂H₈N₂)₂]	V = 2379 (2) Å³
M_r = 571.59	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.046 (7) Å	µ = 1.90 mm⁻¹
b = 13.470 (7) Å	T = 293 K
c = 13.538 (7) Å	0.30 × 0.15 × 0.12 mm
β = 90.044 (9)°

Data collection top

Bruker SMART CCD diffractometer	4959 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	3662 reflections with I > 2σ(I)
T_min = 0.599, T_max = 0.804	R_int = 0.081
15496 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.00	Δρ_max = 0.47 e Å⁻³
4959 reflections	Δρ_min = −0.57 e Å⁻³
316 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
Cu1	0.08441 (4)	0.73813 (3)	0.04132 (4)	0.06012 (19)
Cu2	0.45032 (3)	0.76203 (3)	−0.04863 (3)	0.05589 (18)
C1	0.3089 (3)	0.7520 (2)	−0.0233 (3)	0.0502 (8)
N2	0.5019 (2)	0.8164 (2)	−0.1747 (2)	0.0623 (7)
N3	−0.0405 (2)	0.73312 (19)	−0.0551 (2)	0.0557 (7)
N4	0.0024 (2)	0.86301 (19)	0.0898 (2)	0.0524 (6)
N5	0.54334 (18)	0.8232 (2)	0.06500 (19)	0.0501 (6)
N6	0.5591 (2)	0.64667 (19)	−0.02813 (19)	0.0515 (6)
N1	0.2232 (2)	0.74724 (19)	−0.0059 (2)	0.0619 (8)
C2	0.5338 (2)	0.8478 (2)	−0.2473 (2)	0.0505 (7)
C3	−0.0636 (3)	0.6686 (3)	−0.1262 (3)	0.0712 (10)
H3A	−0.0226	0.6125	−0.1325	0.085*
C4	−0.1433 (4)	0.6793 (3)	−0.1905 (4)	0.0901 (14)
H4A	−0.1549	0.6324	−0.2397	0.108*
C5	−0.2064 (4)	0.7608 (3)	−0.1815 (4)	0.0854 (15)
H5A	−0.2610	0.7697	−0.2248	0.103*
C6	−0.1878 (2)	0.8295 (2)	−0.1071 (3)	0.0609 (9)
C7	−0.2500 (3)	0.9176 (3)	−0.0924 (3)	0.0709 (10)
H7A	−0.3060	0.9296	−0.1333	0.085*
C8	−0.2269 (3)	0.9819 (3)	−0.0200 (3)	0.0662 (10)
H8A	−0.2675	1.0380	−0.0119	0.079*
C9	−0.1417 (2)	0.9670 (2)	0.0451 (3)	0.0523 (7)
C10	−0.1156 (3)	1.0327 (2)	0.1207 (3)	0.0597 (9)
H10A	−0.1545	1.0896	0.1311	0.072*
C11	−0.0333 (3)	1.0133 (3)	0.1790 (3)	0.0682 (10)
H11A	−0.0155	1.0563	0.2299	0.082*
C12	0.0254 (3)	0.9263 (3)	0.1610 (2)	0.0625 (9)
H12A	0.0820	0.9135	0.2008	0.075*
C13	−0.0798 (2)	0.8824 (2)	0.0330 (2)	0.0473 (7)
C14	−0.1038 (2)	0.8128 (2)	−0.0458 (2)	0.0502 (7)
C15	0.5371 (3)	0.9102 (3)	0.1122 (3)	0.0639 (9)
H15A	0.4849	0.9536	0.0943	0.077*
C16	0.6044 (3)	0.9392 (3)	0.1865 (3)	0.0747 (10)
H16A	0.5968	1.0008	0.2167	0.090*
C17	0.6812 (3)	0.8776 (3)	0.2149 (3)	0.0733 (10)
H17A	0.7253	0.8954	0.2659	0.088*
C18	0.6929 (3)	0.7856 (3)	0.1653 (3)	0.0559 (8)
C19	0.7759 (3)	0.7185 (3)	0.1877 (3)	0.0692 (10)
H19A	0.8219	0.7332	0.2382	0.083*
C20	0.7865 (3)	0.6345 (3)	0.1351 (3)	0.0696 (10)
H20A	0.8424	0.5937	0.1478	0.084*
C21	0.7157 (2)	0.6058 (2)	0.0611 (3)	0.0581 (8)
C22	0.7226 (3)	0.5174 (3)	0.0063 (3)	0.0743 (12)
H22A	0.7770	0.4740	0.0168	0.089*
C23	0.6491 (3)	0.4955 (3)	−0.0622 (3)	0.0783 (12)
H23A	0.6530	0.4370	−0.0985	0.094*
C24	0.5680 (3)	0.5616 (3)	−0.0775 (3)	0.0641 (9)
H24A	0.5182	0.5455	−0.1240	0.077*
C25	0.6313 (2)	0.6691 (2)	0.0399 (2)	0.0471 (7)
C26	0.6224 (3)	0.7617 (2)	0.0929 (2)	0.0468 (7)
S1	0.58145 (8)	0.89734 (6)	−0.34839 (7)	0.0644 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0442 (3)	0.0592 (3)	0.0770 (4)	0.01178 (17)	0.0058 (2)	0.00483 (19)
Cu2	0.0407 (3)	0.0623 (3)	0.0646 (3)	0.00543 (17)	−0.0032 (2)	0.00538 (18)
C1	0.0387 (17)	0.0418 (15)	0.070 (2)	0.0058 (12)	0.0049 (15)	0.0057 (13)
N2	0.0498 (15)	0.0711 (19)	0.0659 (18)	−0.0020 (14)	−0.0025 (13)	0.0112 (15)
N3	0.0468 (16)	0.0429 (14)	0.077 (2)	0.0043 (11)	0.0045 (15)	−0.0008 (12)
N4	0.0538 (14)	0.0452 (13)	0.0582 (15)	0.0046 (12)	0.0092 (12)	0.0053 (12)
N5	0.0421 (13)	0.0504 (14)	0.0577 (15)	0.0087 (11)	0.0024 (11)	−0.0010 (12)
N6	0.0503 (14)	0.0457 (14)	0.0584 (15)	0.0028 (11)	0.0049 (12)	0.0001 (12)
N1	0.0516 (19)	0.0502 (16)	0.084 (2)	0.0083 (12)	0.0027 (16)	0.0065 (14)
C2	0.0389 (14)	0.0447 (16)	0.068 (2)	0.0002 (13)	−0.0035 (14)	−0.0008 (14)
C3	0.061 (2)	0.056 (2)	0.097 (3)	0.0088 (17)	−0.003 (2)	−0.023 (2)
C4	0.084 (3)	0.067 (3)	0.119 (4)	0.008 (2)	−0.017 (3)	−0.036 (3)
C5	0.060 (3)	0.069 (3)	0.127 (4)	0.0007 (19)	−0.027 (3)	−0.022 (2)
C6	0.0396 (15)	0.0487 (17)	0.094 (3)	−0.0007 (14)	−0.0049 (16)	−0.0069 (17)
C7	0.0495 (18)	0.0507 (19)	0.113 (3)	0.0065 (16)	−0.0176 (19)	−0.005 (2)
C8	0.0518 (19)	0.0413 (17)	0.106 (3)	0.0098 (15)	−0.0004 (19)	0.0024 (18)
C9	0.0471 (16)	0.0394 (15)	0.071 (2)	0.0027 (13)	0.0081 (15)	0.0049 (14)
C10	0.067 (2)	0.0431 (17)	0.069 (2)	0.0091 (15)	0.0118 (18)	0.0027 (15)
C11	0.089 (3)	0.056 (2)	0.060 (2)	0.006 (2)	0.004 (2)	0.0001 (16)
C12	0.071 (2)	0.060 (2)	0.0563 (19)	0.0092 (18)	−0.0005 (16)	0.0008 (16)
C13	0.0384 (14)	0.0383 (15)	0.0653 (18)	0.0014 (12)	0.0091 (13)	0.0044 (13)
C14	0.0395 (14)	0.0389 (15)	0.072 (2)	0.0000 (12)	0.0074 (14)	0.0024 (14)
C15	0.0590 (19)	0.060 (2)	0.072 (2)	0.0170 (17)	0.0047 (17)	−0.0110 (17)
C16	0.078 (2)	0.074 (2)	0.072 (2)	0.011 (2)	−0.001 (2)	−0.023 (2)
C17	0.071 (2)	0.085 (3)	0.065 (2)	−0.006 (2)	−0.0035 (18)	−0.016 (2)
C18	0.0430 (17)	0.066 (2)	0.0590 (19)	−0.0033 (16)	−0.0031 (14)	0.0115 (17)
C19	0.049 (2)	0.086 (3)	0.072 (2)	0.003 (2)	−0.0150 (17)	0.017 (2)
C20	0.0497 (18)	0.073 (2)	0.086 (3)	0.0160 (18)	−0.0044 (18)	0.030 (2)
C21	0.0468 (17)	0.0500 (18)	0.077 (2)	0.0118 (14)	0.0091 (16)	0.0149 (16)
C22	0.072 (3)	0.052 (2)	0.099 (3)	0.0215 (19)	0.020 (2)	0.013 (2)
C23	0.092 (3)	0.047 (2)	0.097 (3)	0.012 (2)	0.021 (3)	−0.005 (2)
C24	0.075 (2)	0.0519 (18)	0.065 (2)	0.0020 (17)	0.0054 (17)	−0.0055 (16)
C25	0.0397 (14)	0.0446 (15)	0.0570 (17)	0.0076 (12)	0.0079 (13)	0.0080 (13)
C26	0.0429 (17)	0.0476 (16)	0.0500 (17)	0.0051 (12)	0.0054 (14)	0.0045 (12)
S1	0.0725 (6)	0.0491 (5)	0.0717 (6)	−0.0137 (4)	0.0150 (5)	−0.0022 (4)

Geometric parameters (Å, º) top

Cu1—N1	1.924 (3)	C8—H8A	0.9300
Cu1—N3	2.089 (3)	C9—C10	1.395 (5)
Cu1—N4	2.099 (3)	C9—C13	1.406 (4)
Cu1—S1ⁱ	2.3581 (13)	C10—C11	1.358 (5)
Cu2—C1	1.882 (3)	C10—H10A	0.9300
Cu2—N2	1.976 (3)	C11—C12	1.420 (5)
Cu2—N6	2.123 (3)	C11—H11A	0.9300
Cu2—N5	2.125 (3)	C12—H12A	0.9300
C1—N1	1.145 (5)	C13—C14	1.454 (5)
N2—C2	1.148 (4)	C15—C16	1.391 (5)
N3—C3	1.331 (5)	C15—H15A	0.9300
N3—C14	1.360 (4)	C16—C17	1.356 (6)
N4—C12	1.322 (4)	C16—H16A	0.9300
N4—C13	1.345 (4)	C17—C18	1.417 (5)
N5—C15	1.336 (4)	C17—H17A	0.9300
N5—C26	1.376 (4)	C18—C26	1.382 (5)
N6—C24	1.331 (4)	C18—C19	1.443 (5)
N6—C25	1.351 (4)	C19—C20	1.343 (6)
C2—S1	1.645 (3)	C19—H19A	0.9300
C3—C4	1.363 (6)	C20—C21	1.416 (5)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.377 (6)	C21—C22	1.406 (5)
C4—H4A	0.9300	C21—C25	1.421 (4)
C5—C6	1.390 (6)	C22—C23	1.366 (6)
C5—H5A	0.9300	C22—H22A	0.9300
C6—C14	1.392 (5)	C23—C24	1.399 (5)
C6—C7	1.452 (5)	C23—H23A	0.9300
C7—C8	1.341 (5)	C24—H24A	0.9300
C7—H7A	0.9300	C25—C26	1.444 (4)
C8—C9	1.433 (5)	S1—Cu1ⁱⁱ	2.3581 (13)

N1—Cu1—N3	121.90 (14)	C9—C10—H10A	120.1
N1—Cu1—N4	122.18 (11)	C10—C11—C12	119.1 (3)
N3—Cu1—N4	79.83 (11)	C10—C11—H11A	120.5
N1—Cu1—S1ⁱ	105.99 (9)	C12—C11—H11A	120.5
N3—Cu1—S1ⁱ	110.96 (8)	N4—C12—C11	122.4 (3)
N4—Cu1—S1ⁱ	114.43 (8)	N4—C12—H12A	118.8
C1—Cu2—N2	121.25 (14)	C11—C12—H12A	118.8
C1—Cu2—N6	125.39 (12)	N4—C13—C9	123.2 (3)
N2—Cu2—N6	98.99 (11)	N4—C13—C14	117.7 (3)
C1—Cu2—N5	117.10 (13)	C9—C13—C14	119.0 (3)
N2—Cu2—N5	106.65 (12)	N3—C14—C6	123.4 (3)
N6—Cu2—N5	78.93 (11)	N3—C14—C13	116.6 (3)
N1—C1—Cu2	178.3 (4)	C6—C14—C13	120.1 (3)
C2—N2—Cu2	178.7 (3)	N5—C15—C16	123.6 (3)
C3—N3—C14	116.5 (3)	N5—C15—H15A	118.2
C3—N3—Cu1	130.5 (2)	C16—C15—H15A	118.2
C14—N3—Cu1	112.9 (2)	C17—C16—C15	119.9 (4)
C12—N4—C13	118.2 (3)	C17—C16—H16A	120.1
C12—N4—Cu1	129.0 (2)	C15—C16—H16A	120.1
C13—N4—Cu1	112.6 (2)	C16—C17—C18	118.8 (4)
C15—N5—C26	116.2 (3)	C16—C17—H17A	120.6
C15—N5—Cu2	130.6 (2)	C18—C17—H17A	120.6
C26—N5—Cu2	113.1 (2)	C26—C18—C17	117.9 (3)
C24—N6—C25	118.3 (3)	C26—C18—C19	120.1 (4)
C24—N6—Cu2	128.5 (3)	C17—C18—C19	122.0 (4)
C25—N6—Cu2	113.0 (2)	C20—C19—C18	119.6 (4)
C1—N1—Cu1	172.5 (4)	C20—C19—H19A	120.2
N2—C2—S1	177.3 (3)	C18—C19—H19A	120.2
N3—C3—C4	124.4 (4)	C19—C20—C21	122.5 (3)
N3—C3—H3A	117.8	C19—C20—H20A	118.7
C4—C3—H3A	117.8	C21—C20—H20A	118.7
C3—C4—C5	118.9 (4)	C22—C21—C20	124.2 (3)
C3—C4—H4A	120.5	C22—C21—C25	116.8 (4)
C5—C4—H4A	120.5	C20—C21—C25	118.9 (3)
C4—C5—C6	119.4 (4)	C23—C22—C21	119.7 (3)
C4—C5—H5A	120.3	C23—C22—H22A	120.1
C6—C5—H5A	120.3	C21—C22—H22A	120.1
C14—C6—C5	117.5 (3)	C22—C23—C24	119.5 (4)
C14—C6—C7	119.4 (3)	C22—C23—H23A	120.2
C5—C6—C7	123.1 (4)	C24—C23—H23A	120.2
C8—C7—C6	120.1 (3)	N6—C24—C23	122.7 (4)
C8—C7—H7A	119.9	N6—C24—H24A	118.7
C6—C7—H7A	119.9	C23—C24—H24A	118.7
C7—C8—C9	122.2 (3)	N6—C25—C21	122.9 (3)
C7—C8—H8A	118.9	N6—C25—C26	118.4 (3)
C9—C8—H8A	118.9	C21—C25—C26	118.7 (3)
C10—C9—C13	117.4 (3)	N5—C26—C18	123.6 (3)
C10—C9—C8	123.4 (3)	N5—C26—C25	116.4 (3)
C13—C9—C8	119.1 (3)	C18—C26—C25	120.0 (3)
C11—C10—C9	119.7 (3)	C2—S1—Cu1ⁱⁱ	102.69 (12)
C11—C10—H10A	120.1

N2—Cu2—C1—N1	−122 (11)	Cu1—N4—C13—C14	4.5 (3)
N6—Cu2—C1—N1	107 (11)	C10—C9—C13—N4	−0.5 (4)
N5—Cu2—C1—N1	11 (11)	C8—C9—C13—N4	179.1 (3)
C1—Cu2—N2—C2	178 (100)	C10—C9—C13—C14	−179.2 (3)
N6—Cu2—N2—C2	−41 (13)	C8—C9—C13—C14	0.3 (4)
N5—Cu2—N2—C2	40 (13)	C3—N3—C14—C6	−1.2 (5)
N1—Cu1—N3—C3	59.4 (4)	Cu1—N3—C14—C6	175.1 (3)
N4—Cu1—N3—C3	−178.9 (3)	C3—N3—C14—C13	178.9 (3)
S1ⁱ—Cu1—N3—C3	−66.5 (3)	Cu1—N3—C14—C13	−4.8 (4)
N1—Cu1—N3—C14	−116.3 (2)	C5—C6—C14—N3	−0.3 (5)
N4—Cu1—N3—C14	5.5 (2)	C7—C6—C14—N3	−179.0 (3)
S1ⁱ—Cu1—N3—C14	117.9 (2)	C5—C6—C14—C13	179.6 (4)
N1—Cu1—N4—C12	−58.1 (3)	C7—C6—C14—C13	0.9 (5)
N3—Cu1—N4—C12	−179.6 (3)	N4—C13—C14—N3	0.2 (4)
S1ⁱ—Cu1—N4—C12	71.9 (3)	C9—C13—C14—N3	179.0 (3)
N1—Cu1—N4—C13	116.1 (2)	N4—C13—C14—C6	−179.7 (3)
N3—Cu1—N4—C13	−5.3 (2)	C9—C13—C14—C6	−0.9 (4)
S1ⁱ—Cu1—N4—C13	−113.87 (19)	C26—N5—C15—C16	−0.8 (5)
C1—Cu2—N5—C15	−55.7 (3)	Cu2—N5—C15—C16	179.4 (3)
N2—Cu2—N5—C15	83.8 (3)	N5—C15—C16—C17	−0.3 (6)
N6—Cu2—N5—C15	−180.0 (3)	C15—C16—C17—C18	2.0 (6)
C1—Cu2—N5—C26	124.4 (2)	C16—C17—C18—C26	−2.6 (5)
N2—Cu2—N5—C26	−96.0 (2)	C16—C17—C18—C19	176.6 (4)
N6—Cu2—N5—C26	0.2 (2)	C26—C18—C19—C20	2.5 (5)
C1—Cu2—N6—C24	67.3 (3)	C17—C18—C19—C20	−176.7 (4)
N2—Cu2—N6—C24	−71.8 (3)	C18—C19—C20—C21	−3.5 (6)
N5—Cu2—N6—C24	−177.2 (3)	C19—C20—C21—C22	−178.3 (4)
C1—Cu2—N6—C25	−117.6 (2)	C19—C20—C21—C25	1.4 (5)
N2—Cu2—N6—C25	103.2 (2)	C20—C21—C22—C23	178.7 (3)
N5—Cu2—N6—C25	−2.1 (2)	C25—C21—C22—C23	−0.9 (5)
Cu2—C1—N1—Cu1	−39 (13)	C21—C22—C23—C24	0.3 (6)
N3—Cu1—N1—C1	−177 (2)	C25—N6—C24—C23	−0.6 (5)
N4—Cu1—N1—C1	85 (2)	Cu2—N6—C24—C23	174.2 (3)
S1ⁱ—Cu1—N1—C1	−49 (2)	C22—C23—C24—N6	0.5 (6)
Cu2—N2—C2—S1	−66 (17)	C24—N6—C25—C21	−0.2 (4)
C14—N3—C3—C4	2.1 (6)	Cu2—N6—C25—C21	−175.7 (2)
Cu1—N3—C3—C4	−173.4 (3)	C24—N6—C25—C26	179.4 (3)
N3—C3—C4—C5	−1.3 (8)	Cu2—N6—C25—C26	3.9 (3)
C3—C4—C5—C6	−0.3 (8)	C22—C21—C25—N6	0.9 (5)
C4—C5—C6—C14	1.1 (7)	C20—C21—C25—N6	−178.7 (3)
C4—C5—C6—C7	179.7 (4)	C22—C21—C25—C26	−178.7 (3)
C14—C6—C7—C8	−0.4 (6)	C20—C21—C25—C26	1.7 (4)
C5—C6—C7—C8	−179.0 (4)	C15—N5—C26—C18	0.1 (5)
C6—C7—C8—C9	−0.2 (6)	Cu2—N5—C26—C18	180.0 (2)
C7—C8—C9—C10	179.7 (4)	C15—N5—C26—C25	−178.1 (3)
C7—C8—C9—C13	0.2 (5)	Cu2—N5—C26—C25	1.8 (3)
C13—C9—C10—C11	−0.1 (5)	C17—C18—C26—N5	1.6 (5)
C8—C9—C10—C11	−179.7 (3)	C19—C18—C26—N5	−177.7 (3)
C9—C10—C11—C12	0.6 (5)	C17—C18—C26—C25	179.7 (3)
C13—N4—C12—C11	−0.2 (5)	C19—C18—C26—C25	0.5 (5)
Cu1—N4—C12—C11	173.8 (2)	N6—C25—C26—N5	−3.8 (4)
C10—C11—C12—N4	−0.4 (5)	C21—C25—C26—N5	175.8 (3)
C12—N4—C13—C9	0.6 (4)	N6—C25—C26—C18	177.9 (3)
Cu1—N4—C13—C9	−174.3 (2)	C21—C25—C26—C18	−2.5 (4)
C12—N4—C13—C14	179.4 (3)	N2—C2—S1—Cu1ⁱⁱ	163 (6)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(CN)(NCS)(C₁₂H₈N₂)₂]
M_r	571.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.046 (7), 13.470 (7), 13.538 (7)
β (°)	90.044 (9)
V (Å³)	2379 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.30 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.599, 0.804
No. of measured, independent and observed [I > 2σ(I)] reflections	15496, 4959, 3662
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.164, 1.00
No. of reflections	4959
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.57

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

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