catena-Poly[[[2-({6-[(pyrimidin-2-ylsulfanyl-κS)meth-yl]pyridin-2-yl-κN}methyl-sulfan-yl)pyrimidine]-copper(I)]-μ-thio-cyanato-κ(2)N:S].

The N-heterocyclic ligand in the title compound, [Cu(NCS)(C(15)H(13)N(5)S(2))](n), coordinates to the Cu(I) atom through its pyridine N-donor site, and adjacent metal atoms are bridged by the thio-cyanate ion, forming a helical chain along the b axis. The geometry of the metal atom is tetra-hedral owing to a somewhat long intra-molecular Cu-S inter-action of 2.5621 (9) Å.

Related literature

For the synthesis of the N-heterocyle and its copper(I) adducts, see: Peng et al. (2006 ▶).

Experimental

Crystal data

[Cu(NCS)(C15H13N5S2)]

M = 449.04

Monoclinic,

a = 11.1706 (8) Å

b = 8.6735 (6) Å

c = 19.0956 (14) Å

β = 100.978 (1)°

V = 1816.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.56 mm−1

T = 293 K

0.16 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.703, T max = 1.000

10799 measured reflections

4077 independent reflections

3022 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.04

4077 reflections

235 parameters

H-atom parameters constrained

Δρmax = 1.18 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201063X/zs2186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201063X/zs2186Isup2.hkl

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

[Cu(NCS)(C15H13N5S2)]	F(000) = 912
Mr = 449.04	Dx = 1.642 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2743 reflections
a = 11.1706 (8) Å	θ = 2.6–25.0°
b = 8.6735 (6) Å	µ = 1.56 mm−1
c = 19.0956 (14) Å	T = 293 K
β = 100.978 (1)°	Prism, brown
V = 1816.3 (2) Å3	0.16 × 0.11 × 0.06 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4077 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
Tmin = 0.703, Tmax = 1.000	k = −11→4
10799 measured reflections	l = −24→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.7767P] where P = (Fo2 + 2Fc2)/3
4077 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 1.18 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.40542 (4)	0.22472 (5)	0.23431 (3)	0.06021 (17)
S1	0.39013 (7)	0.38008 (9)	0.11883 (4)	0.0492 (2)
S2	0.51157 (8)	0.14604 (12)	0.39459 (5)	0.0604 (2)
S3	0.05933 (8)	0.47654 (10)	0.29022 (5)	0.0583 (2)
N1	0.4820 (3)	0.2133 (3)	0.02977 (15)	0.0547 (7)
N2	0.6034 (2)	0.4274 (3)	0.07782 (14)	0.0522 (6)
N3	0.5545 (2)	0.3694 (3)	0.26678 (12)	0.0404 (5)
N4	0.6536 (3)	0.3205 (4)	0.49195 (15)	0.0615 (8)
N5	0.4632 (3)	0.2354 (4)	0.51544 (18)	0.0740 (9)
N6	0.2579 (3)	0.3150 (3)	0.25756 (16)	0.0560 (7)
C1	0.5066 (3)	0.3375 (4)	0.07088 (15)	0.0425 (6)
C2	0.5642 (3)	0.1795 (4)	−0.00998 (18)	0.0573 (8)
H2	0.5505	0.0949	−0.0404	0.069*
C3	0.6680 (3)	0.2642 (4)	−0.00794 (18)	0.0565 (9)
H3	0.7248	0.2391	−0.0360	0.068*
C4	0.6842 (3)	0.3875 (4)	0.03729 (18)	0.0578 (9)
H4	0.7544	0.4465	0.0401	0.069*
C5	0.4517 (3)	0.5411 (4)	0.17298 (17)	0.0508 (7)
H5A	0.4792	0.6173	0.1424	0.061*
H5B	0.3865	0.5875	0.1928	0.061*
C6	0.5557 (3)	0.5052 (3)	0.23334 (15)	0.0428 (7)
C7	0.6469 (3)	0.6129 (4)	0.25452 (18)	0.0542 (8)
H7	0.6454	0.7066	0.2307	0.065*
C8	0.7392 (3)	0.5806 (5)	0.31075 (19)	0.0611 (9)
H8	0.8015	0.6513	0.3254	0.073*
C9	0.7378 (3)	0.4420 (4)	0.34490 (18)	0.0549 (8)
H9	0.7993	0.4179	0.3834	0.066*
C10	0.6455 (3)	0.3388 (4)	0.32216 (16)	0.0463 (7)
C11	0.6440 (3)	0.1836 (4)	0.35597 (19)	0.0582 (8)
H11A	0.7163	0.1736	0.3930	0.070*
H11B	0.6487	0.1055	0.3202	0.070*
C12	0.5486 (3)	0.2465 (4)	0.47565 (18)	0.0514 (8)
C13	0.6736 (4)	0.3913 (5)	0.5549 (2)	0.0738 (11)
H13	0.7461	0.4454	0.5686	0.089*
C14	0.5936 (4)	0.3884 (6)	0.5997 (2)	0.0797 (12)
H14	0.6095	0.4388	0.6435	0.096*
C15	0.4898 (4)	0.3090 (7)	0.5780 (2)	0.0903 (15)
H15	0.4334	0.3051	0.6080	0.108*
C16	0.1773 (3)	0.3838 (3)	0.26969 (16)	0.0443 (7)

	U11	U22	U33	U12	U13	U23
Cu1	0.0529 (3)	0.0354 (2)	0.0982 (4)	0.00026 (17)	0.0294 (2)	−0.0022 (2)
S1	0.0522 (4)	0.0427 (4)	0.0549 (4)	0.0001 (3)	0.0157 (3)	0.0011 (3)
S2	0.0644 (5)	0.0590 (6)	0.0588 (5)	−0.0066 (4)	0.0142 (4)	0.0121 (4)
S3	0.0532 (5)	0.0343 (4)	0.0968 (7)	0.0037 (3)	0.0376 (4)	0.0064 (4)
N1	0.0595 (17)	0.0439 (16)	0.0633 (16)	−0.0106 (13)	0.0185 (13)	−0.0113 (13)
N2	0.0567 (16)	0.0472 (16)	0.0533 (15)	−0.0099 (13)	0.0123 (12)	−0.0070 (12)
N3	0.0459 (13)	0.0321 (13)	0.0478 (13)	0.0040 (10)	0.0206 (11)	0.0004 (10)
N4	0.0522 (17)	0.075 (2)	0.0563 (17)	−0.0033 (15)	0.0080 (13)	0.0150 (15)
N5	0.0558 (18)	0.095 (3)	0.076 (2)	−0.0009 (17)	0.0254 (15)	0.0030 (19)
N6	0.0511 (15)	0.0437 (15)	0.0782 (18)	0.0038 (13)	0.0252 (14)	0.0003 (14)
C1	0.0507 (16)	0.0363 (15)	0.0401 (14)	0.0009 (13)	0.0080 (12)	0.0061 (12)
C2	0.066 (2)	0.0468 (18)	0.0612 (19)	−0.0061 (16)	0.0175 (17)	−0.0147 (16)
C3	0.057 (2)	0.058 (2)	0.0585 (19)	0.0017 (16)	0.0199 (16)	−0.0053 (16)
C4	0.0519 (18)	0.061 (2)	0.063 (2)	−0.0144 (16)	0.0168 (16)	−0.0090 (17)
C5	0.066 (2)	0.0342 (16)	0.0550 (17)	0.0072 (15)	0.0190 (15)	0.0018 (14)
C6	0.0543 (16)	0.0332 (15)	0.0477 (15)	0.0029 (13)	0.0268 (13)	−0.0035 (12)
C7	0.068 (2)	0.0411 (17)	0.0615 (19)	−0.0099 (16)	0.0331 (17)	−0.0036 (15)
C8	0.059 (2)	0.063 (2)	0.067 (2)	−0.0173 (18)	0.0274 (18)	−0.0150 (18)
C9	0.0469 (17)	0.065 (2)	0.0551 (18)	0.0031 (16)	0.0159 (14)	−0.0075 (17)
C10	0.0495 (17)	0.0447 (17)	0.0506 (17)	0.0086 (14)	0.0244 (14)	0.0015 (14)
C11	0.063 (2)	0.057 (2)	0.0587 (19)	0.0121 (17)	0.0203 (16)	0.0087 (17)
C12	0.0459 (17)	0.0512 (19)	0.0583 (18)	0.0115 (14)	0.0133 (14)	0.0189 (15)
C13	0.075 (3)	0.076 (3)	0.064 (2)	−0.008 (2)	−0.001 (2)	0.010 (2)
C14	0.091 (3)	0.081 (3)	0.067 (2)	0.017 (3)	0.014 (2)	−0.004 (2)
C15	0.078 (3)	0.128 (4)	0.076 (3)	0.016 (3)	0.040 (2)	−0.006 (3)
C16	0.0457 (16)	0.0334 (15)	0.0566 (17)	−0.0040 (13)	0.0166 (13)	0.0032 (13)

Cu1—N6	1.951 (3)	C2—H2	0.9300
Cu1—N3	2.083 (2)	C3—C4	1.364 (5)
Cu1—S3i	2.2536 (9)	C3—H3	0.9300
Cu1—S1	2.5621 (9)	C4—H4	0.9300
S1—C1	1.767 (3)	C5—C6	1.505 (4)
S1—C5	1.794 (3)	C5—H5A	0.9700
S2—C12	1.756 (4)	C5—H5B	0.9700
S2—C11	1.804 (3)	C6—C7	1.385 (4)
S3—C16	1.653 (3)	C7—C8	1.369 (5)
S3—Cu1ii	2.2536 (9)	C7—H7	0.9300
N1—C1	1.331 (4)	C8—C9	1.369 (5)
N1—C2	1.331 (4)	C8—H8	0.9300
N2—C1	1.319 (4)	C9—C10	1.372 (5)
N2—C4	1.341 (4)	C9—H9	0.9300
N3—C6	1.341 (4)	C10—C11	1.494 (5)
N3—C10	1.346 (4)	C11—H11A	0.9700
N4—C12	1.322 (4)	C11—H11B	0.9700
N4—C13	1.329 (5)	C13—C14	1.351 (6)
N5—C12	1.331 (4)	C13—H13	0.9300
N5—C15	1.337 (6)	C14—C15	1.344 (7)
N6—C16	1.140 (4)	C14—H14	0.9300
C2—C3	1.367 (5)	C15—H15	0.9300
N6—Cu1—N3	110.66 (11)	H5A—C5—H5B	107.4
N6—Cu1—S3i	128.26 (9)	N3—C6—C7	121.8 (3)
N3—Cu1—S3i	118.42 (7)	N3—C6—C5	118.0 (3)
N6—Cu1—S1	93.67 (9)	C7—C6—C5	120.1 (3)
N3—Cu1—S1	81.83 (7)	C8—C7—C6	119.6 (3)
S3i—Cu1—S1	108.00 (4)	C8—C7—H7	120.2
C1—S1—C5	102.84 (15)	C6—C7—H7	120.2
C1—S1—Cu1	113.65 (10)	C7—C8—C9	118.6 (3)
C5—S1—Cu1	87.58 (10)	C7—C8—H8	120.7
C12—S2—C11	101.37 (17)	C9—C8—H8	120.7
C16—S3—Cu1ii	103.70 (10)	C8—C9—C10	119.9 (3)
C1—N1—C2	115.3 (3)	C8—C9—H9	120.1
C1—N2—C4	114.7 (3)	C10—C9—H9	120.1
C6—N3—C10	118.2 (3)	N3—C10—C9	122.0 (3)
C6—N3—Cu1	117.9 (2)	N3—C10—C11	116.6 (3)
C10—N3—Cu1	123.8 (2)	C9—C10—C11	121.4 (3)
C12—N4—C13	115.2 (3)	C10—C11—S2	114.6 (2)
C12—N5—C15	114.5 (3)	C10—C11—H11A	108.6
C16—N6—Cu1	172.1 (3)	S2—C11—H11A	108.6
N2—C1—N1	127.7 (3)	C10—C11—H11B	108.6
N2—C1—S1	119.7 (2)	S2—C11—H11B	108.6
N1—C1—S1	112.6 (2)	H11A—C11—H11B	107.6
N1—C2—C3	122.7 (3)	N4—C12—N5	127.0 (3)
N1—C2—H2	118.7	N4—C12—S2	119.9 (2)
C3—C2—H2	118.7	N5—C12—S2	113.2 (3)
C4—C3—C2	116.6 (3)	N4—C13—C14	123.2 (4)
C4—C3—H3	121.7	N4—C13—H13	118.4
C2—C3—H3	121.7	C14—C13—H13	118.4
N2—C4—C3	123.0 (3)	C15—C14—C13	116.7 (4)
N2—C4—H4	118.5	C15—C14—H14	121.7
C3—C4—H4	118.5	C13—C14—H14	121.7
C6—C5—S1	115.8 (2)	N5—C15—C14	123.5 (4)
C6—C5—H5A	108.3	N5—C15—H15	118.2
S1—C5—H5A	108.3	C14—C15—H15	118.2
C6—C5—H5B	108.3	N6—C16—S3	177.0 (3)
S1—C5—H5B	108.3
N6—Cu1—S1—C1	−178.20 (14)	C10—N3—C6—C5	−178.1 (2)
N3—Cu1—S1—C1	71.44 (13)	Cu1—N3—C6—C5	−2.2 (3)
S3i—Cu1—S1—C1	−45.88 (12)	S1—C5—C6—N3	−35.0 (3)
N6—Cu1—S1—C5	78.83 (14)	S1—C5—C6—C7	147.2 (2)
N3—Cu1—S1—C5	−31.53 (12)	N3—C6—C7—C8	0.5 (4)
S3i—Cu1—S1—C5	−148.84 (11)	C5—C6—C7—C8	178.2 (3)
N6—Cu1—N3—C6	−67.0 (2)	C6—C7—C8—C9	−0.5 (5)
S3i—Cu1—N3—C6	129.96 (18)	C7—C8—C9—C10	0.4 (5)
S1—Cu1—N3—C6	23.86 (18)	C6—N3—C10—C9	0.2 (4)
N6—Cu1—N3—C10	108.6 (2)	Cu1—N3—C10—C9	−175.4 (2)
S3i—Cu1—N3—C10	−54.4 (2)	C6—N3—C10—C11	−177.3 (2)
S1—Cu1—N3—C10	−160.5 (2)	Cu1—N3—C10—C11	7.0 (3)
C4—N2—C1—N1	1.0 (5)	C8—C9—C10—N3	−0.3 (5)
C4—N2—C1—S1	−177.9 (2)	C8—C9—C10—C11	177.2 (3)
C2—N1—C1—N2	−1.8 (5)	N3—C10—C11—S2	−61.7 (3)
C2—N1—C1—S1	177.2 (3)	C9—C10—C11—S2	120.8 (3)
C5—S1—C1—N2	−4.7 (3)	C12—S2—C11—C10	−79.1 (3)
Cu1—S1—C1—N2	−97.7 (2)	C13—N4—C12—N5	−0.5 (6)
C5—S1—C1—N1	176.2 (2)	C13—N4—C12—S2	−179.2 (3)
Cu1—S1—C1—N1	83.2 (2)	C15—N5—C12—N4	0.3 (6)
C1—N1—C2—C3	1.2 (5)	C15—N5—C12—S2	179.1 (3)
N1—C2—C3—C4	−0.2 (6)	C11—S2—C12—N4	−0.6 (3)
C1—N2—C4—C3	0.3 (5)	C11—S2—C12—N5	−179.5 (3)
C2—C3—C4—N2	−0.7 (5)	C12—N4—C13—C14	0.3 (6)
C1—S1—C5—C6	−71.3 (2)	N4—C13—C14—C15	0.0 (7)
Cu1—S1—C5—C6	42.4 (2)	C12—N5—C15—C14	0.1 (7)
C10—N3—C6—C7	−0.3 (4)	C13—C14—C15—N5	−0.2 (8)
Cu1—N3—C6—C7	175.6 (2)