catena-Poly[[[2-(pyridin-2-yldisulfan-yl)pyridine-κN,S]copper(I)]-μ(1,5)-dicyanamido].

In the title compound, [Cu(C(2)N(3))(C(10)H(8)N(2)S(2))](n), the Cu(I) atoms are connected by bridging dicyanamide ligands, forming chains parallel to [100]. Each Cu(I) atom displays a tetra-hedral coordination environment, formed by one S atom and three N atoms from one 2-(pyridin-2-yldisulfan-yl)pyridine and two dicyanamide ligands. The crystal structure is stabilized by C-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For potential applications of metal-organic frameworks, see: Eddaoudi et al. (2001 ▶). For metal-organic frameworks constructed from flexible ligands, see: Xu et al. (2009 ▶). For related structures, see: Mal et al. (2006 ▶); Schlueter et al. (2007 ▶); Sen et al. (2007 ▶).

Experimental

Crystal data

[Cu(C2N3)(C10H8N2S2)]

M = 349.92

Triclinic,

a = 7.6294 (15) Å

b = 9.5964 (19) Å

c = 10.202 (2) Å

α = 84.19 (3)°

β = 80.63 (3)°

γ = 70.93 (3)°

V = 695.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.87 mm−1

T = 293 K

0.20 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.893, T max = 1.000

6615 measured reflections

2669 independent reflections

2301 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.081

S = 1.07

2669 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002728/zq2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002728/zq2085Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C2N3)(C10H8N2S2)]	Z = 2
Mr = 349.92	F(000) = 352
Triclinic, P1	Dx = 1.671 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6294 (15) Å	Cell parameters from 3088 reflections
b = 9.5964 (19) Å	θ = 3.0–28.9°
c = 10.202 (2) Å	µ = 1.87 mm−1
α = 84.19 (3)°	T = 293 K
β = 80.63 (3)°	Block, colourless
γ = 70.93 (3)°	0.20 × 0.16 × 0.12 mm
V = 695.6 (2) Å3

Bruker APEXII CCD diffractometer	2669 independent reflections
Radiation source: fine-focus sealed tube	2301 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.893, Tmax = 1.000	k = −11→11
6615 measured reflections	l = −12→12

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.0204P] where P = (Fo2 + 2Fc2)/3
2669 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	−0.03943 (3)	0.83530 (3)	0.16964 (3)	0.05693 (13)
S1	−0.00326 (7)	0.67390 (7)	0.37486 (5)	0.05609 (17)
S2	0.11161 (9)	0.47767 (7)	0.28919 (5)	0.06255 (18)
N1	−0.3026 (2)	0.9293 (2)	0.16879 (19)	0.0580 (5)
N2	0.1131 (2)	0.9633 (2)	0.17961 (19)	0.0599 (5)
N3	−0.6377 (2)	1.0592 (2)	0.2077 (2)	0.0694 (6)
N4	0.3589 (3)	0.6469 (2)	0.38308 (18)	0.0610 (5)
N5	0.1249 (2)	0.65814 (18)	0.06703 (15)	0.0464 (4)
C1	−0.4605 (3)	0.9840 (2)	0.1839 (2)	0.0489 (5)
C2	0.2361 (3)	1.0016 (2)	0.1905 (2)	0.0480 (5)
C3	0.1841 (3)	0.7106 (2)	0.43562 (18)	0.0452 (4)
C4	0.1311 (3)	0.8103 (3)	0.5330 (2)	0.0612 (6)
H4	0.0059	0.8499	0.5684	0.073*
C5	0.2682 (4)	0.8504 (3)	0.5770 (2)	0.0709 (7)
H5	0.2372	0.9197	0.6414	0.085*
C6	0.4516 (4)	0.7863 (3)	0.5242 (2)	0.0692 (7)
H6	0.5475	0.8109	0.5519	0.083*
C7	0.4889 (3)	0.6858 (3)	0.4302 (2)	0.0695 (7)
H7	0.6136	0.6409	0.3963	0.083*
C8	0.1811 (3)	0.5212 (2)	0.11824 (18)	0.0462 (5)
C9	0.2919 (4)	0.4027 (2)	0.0454 (2)	0.0627 (6)
H9	0.3245	0.3078	0.0850	0.075*
C10	0.3528 (4)	0.4264 (3)	−0.0852 (2)	0.0681 (7)
H10	0.4289	0.3484	−0.1362	0.082*
C11	0.2996 (4)	0.5682 (3)	−0.1403 (2)	0.0660 (6)
H11	0.3402	0.5877	−0.2292	0.079*
C12	0.1868 (3)	0.6795 (2)	−0.0633 (2)	0.0568 (5)
H12	0.1505	0.7748	−0.1019	0.068*

	U11	U22	U33	U12	U13	U23
Cu1	0.03597 (17)	0.0595 (2)	0.0745 (2)	−0.01273 (13)	−0.00278 (13)	−0.01572 (14)
S1	0.0434 (3)	0.0798 (4)	0.0469 (3)	−0.0244 (3)	0.0007 (2)	−0.0063 (3)
S2	0.0847 (4)	0.0645 (4)	0.0502 (3)	−0.0423 (3)	−0.0082 (3)	0.0048 (3)
N1	0.0393 (10)	0.0623 (11)	0.0748 (12)	−0.0157 (9)	−0.0099 (8)	−0.0125 (9)
N2	0.0394 (10)	0.0572 (11)	0.0836 (13)	−0.0155 (9)	−0.0067 (9)	−0.0086 (10)
N3	0.0382 (10)	0.0433 (10)	0.1278 (17)	−0.0077 (8)	−0.0184 (10)	−0.0154 (11)
N4	0.0464 (10)	0.0763 (13)	0.0606 (10)	−0.0187 (9)	0.0016 (8)	−0.0213 (10)
N5	0.0448 (9)	0.0463 (9)	0.0459 (9)	−0.0120 (7)	−0.0051 (7)	−0.0025 (7)
C1	0.0433 (12)	0.0430 (10)	0.0654 (12)	−0.0170 (9)	−0.0154 (10)	−0.0011 (9)
C2	0.0353 (10)	0.0381 (10)	0.0647 (12)	−0.0040 (8)	−0.0064 (9)	−0.0028 (9)
C3	0.0450 (11)	0.0532 (11)	0.0357 (9)	−0.0147 (9)	−0.0049 (8)	0.0008 (9)
C4	0.0542 (13)	0.0674 (14)	0.0528 (11)	−0.0058 (11)	−0.0028 (10)	−0.0145 (11)
C5	0.0843 (18)	0.0700 (15)	0.0601 (13)	−0.0197 (14)	−0.0148 (12)	−0.0186 (12)
C6	0.0719 (16)	0.0802 (17)	0.0667 (14)	−0.0325 (14)	−0.0237 (13)	−0.0036 (13)
C7	0.0453 (12)	0.0879 (18)	0.0762 (15)	−0.0188 (12)	−0.0066 (11)	−0.0184 (14)
C8	0.0496 (11)	0.0484 (11)	0.0467 (10)	−0.0227 (9)	−0.0093 (9)	−0.0022 (9)
C9	0.0802 (17)	0.0417 (11)	0.0665 (14)	−0.0190 (11)	−0.0118 (12)	−0.0030 (11)
C10	0.0834 (18)	0.0525 (13)	0.0635 (14)	−0.0162 (12)	0.0008 (12)	−0.0167 (11)
C11	0.0817 (17)	0.0652 (15)	0.0466 (11)	−0.0200 (13)	0.0006 (11)	−0.0081 (11)
C12	0.0596 (13)	0.0518 (12)	0.0520 (11)	−0.0108 (10)	−0.0056 (10)	0.0024 (10)

Cu1—N1	1.9143 (18)	C3—C4	1.369 (3)
Cu1—N2	1.967 (2)	C4—C5	1.377 (4)
Cu1—N5	2.0244 (18)	C4—H4	0.9300
Cu1—S1	2.4720 (10)	C5—C6	1.373 (4)
S1—C3	1.792 (2)	C5—H5	0.9300
S1—S2	2.0207 (11)	C6—C7	1.361 (4)
S2—C8	1.787 (2)	C6—H6	0.9300
N1—C1	1.138 (3)	C7—H7	0.9300
N2—C2	1.138 (3)	C8—C9	1.378 (3)
N3—C2i	1.298 (3)	C9—C10	1.360 (3)
N3—C1	1.303 (3)	C9—H9	0.9300
N4—C3	1.319 (3)	C10—C11	1.375 (3)
N4—C7	1.337 (3)	C10—H10	0.9300
N5—C8	1.322 (3)	C11—C12	1.359 (3)
N5—C12	1.356 (3)	C11—H11	0.9300
C2—N3ii	1.298 (3)	C12—H12	0.9300
N1—Cu1—N2	117.16 (8)	C6—C5—C4	118.9 (2)
N1—Cu1—N5	126.58 (8)	C6—C5—H5	120.6
N2—Cu1—N5	107.60 (7)	C4—C5—H5	120.6
N1—Cu1—S1	106.75 (7)	C7—C6—C5	118.1 (2)
N2—Cu1—S1	104.29 (6)	C7—C6—H6	121.0
N5—Cu1—S1	87.90 (5)	C5—C6—H6	121.0
C3—S1—S2	105.95 (8)	N4—C7—C6	124.6 (2)
C3—S1—Cu1	102.35 (7)	N4—C7—H7	117.7
S2—S1—Cu1	98.20 (4)	C6—C7—H7	117.7
C8—S2—S1	105.52 (8)	N5—C8—C9	123.48 (18)
C1—N1—Cu1	172.06 (19)	N5—C8—S2	121.22 (16)
C2—N2—Cu1	161.63 (17)	C9—C8—S2	115.29 (16)
C2i—N3—C1	120.23 (19)	C10—C9—C8	119.1 (2)
C3—N4—C7	115.9 (2)	C10—C9—H9	120.5
C8—N5—C12	116.52 (18)	C8—C9—H9	120.5
C8—N5—Cu1	124.88 (13)	C9—C10—C11	118.6 (2)
C12—N5—Cu1	118.59 (14)	C9—C10—H10	120.7
N1—C1—N3	173.2 (2)	C11—C10—H10	120.7
N2—C2—N3ii	173.5 (2)	C12—C11—C10	119.2 (2)
N4—C3—C4	124.4 (2)	C12—C11—H11	120.4
N4—C3—S1	119.92 (16)	C10—C11—H11	120.4
C4—C3—S1	115.61 (16)	N5—C12—C11	123.1 (2)
C3—C4—C5	118.1 (2)	N5—C12—H12	118.5
C3—C4—H4	120.9	C11—C12—H12	118.5
C5—C4—H4	120.9

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N3iii	0.93	2.53	3.453 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N3i	0.93	2.53	3.453 (3)	171

Symmetry code: (i) .