catena-Poly[[[N,N'-bis-(3-methoxy-benzyl-idene)ethyl-enediamine]copper(I)]-μ-thio-cyanato-κN:S].

In the cyrstal structure of the title compound, [Cu(NCS)(C(18)H(20)N(2)O(2))](n), the Cu(I) atom is coordinated in a distorted tetra-hedral geometry by two imino N atoms from a bidentate chelating Schiff base ligand, and one N and one S atoms from two thio-cyanate anions. The thio-cyanate anion bridges the Cu(I) atoms, forming a zigzag chain along [101]. The Schiff base ligand adopts an E,E configuration and the dihedral angle between the terminal benzene rings is 53.68 (8)°.

Related literature

For related copper(I) complexes with bidentate ligands, see: Amirnasr et al. (2006 ▶); Khalaji, Brad & Zhang (2008 ▶); Khalaji, Welter et al. (2008 ▶); Khalaji & Welter (2006 ▶); Zhao et al. (2008 ▶).

Experimental

Crystal data

[Cu(NCS)(C18H20N2O2)]

M = 417.99

Monoclinic,

a = 8.1316 (3) Å

b = 23.5113 (9) Å

c = 10.1597 (4) Å

β = 107.1245 (15)°

V = 1856.27 (11) Å3

Z = 4

Mo Kα radiation

μ = 1.31 mm−1

T = 193 (1) K

0.31 × 0.17 × 0.02 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (; Higashi, 1995 ▶) T min = 0.771, T max = 0.974

28362 measured reflections

5395 independent reflections

4614 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.076

S = 1.05

5395 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.23 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041925/lh2744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041925/lh2744Isup2.hkl

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

[Cu(NCS)(C18H20N2O2)]	F(000) = 864.00
Mr = 417.99	Dx = 1.496 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 22727 reflections
a = 8.1316 (3) Å	θ = 3.1–30.0°
b = 23.5113 (9) Å	µ = 1.31 mm−1
c = 10.1597 (4) Å	T = 193 K
β = 107.1245 (15)°	Platelet, yellow
V = 1856.27 (11) Å3	0.31 × 0.17 × 0.02 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4614 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.031
ω scans	θmax = 30.0°, θmin = 3.1°
Absorption correction: numerical (ABSCOR; Higashi, 1995)	h = −10→11
Tmin = 0.771, Tmax = 0.974	k = −32→32
28362 measured reflections	l = −14→12
5395 independent reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.7637P] where P = (Fo2 + 2Fc2)/3
5395 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.23 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	0.42300 (2)	0.235166 (8)	0.471370 (18)	0.02525 (6)
S1	0.16168 (5)	0.188164 (18)	0.41646 (4)	0.03209 (9)
O1	−0.06043 (17)	0.34954 (5)	0.56184 (14)	0.0406 (3)
O2	0.46009 (18)	0.04893 (6)	0.71225 (15)	0.0472 (3)
N1	0.01289 (17)	0.24053 (6)	0.16100 (13)	0.0302 (3)
N2	0.41448 (15)	0.30353 (5)	0.33778 (12)	0.0248 (2)
N3	0.61360 (15)	0.20470 (5)	0.38943 (12)	0.0245 (2)
C1	0.07436 (18)	0.21886 (6)	0.26548 (15)	0.0255 (3)
C2	0.3075 (2)	0.38111 (6)	0.44500 (16)	0.0277 (3)
C3	0.1706 (2)	0.35321 (6)	0.47169 (16)	0.0281 (3)
H3	0.1399	0.3160	0.4364	0.034*
C4	0.0781 (2)	0.37944 (6)	0.55001 (15)	0.0294 (3)
C5	0.1271 (2)	0.43268 (7)	0.60751 (18)	0.0374 (4)
H5	0.0657	0.4504	0.6626	0.045*
C6	0.2674 (3)	0.45947 (8)	0.5830 (2)	0.0476 (5)
H6	0.3037	0.4954	0.6240	0.057*
C7	0.3549 (2)	0.43480 (7)	0.5002 (2)	0.0411 (4)
H7	0.4472	0.4545	0.4809	0.049*
C8	−0.1738 (2)	0.37722 (8)	0.6249 (2)	0.0428 (4)
H8A	−0.1147	0.3833	0.7228	0.064*
H8B	−0.2757	0.3534	0.6151	0.064*
H8C	−0.2091	0.4140	0.5800	0.064*
C9	0.39553 (19)	0.35649 (6)	0.35092 (16)	0.0283 (3)
H9	0.4406	0.3817	0.2971	0.034*
C10	0.4946 (2)	0.28431 (7)	0.23429 (15)	0.0289 (3)
H10A	0.5255	0.3175	0.1866	0.035*
H10B	0.4127	0.2604	0.1649	0.035*
C11	0.6547 (2)	0.25029 (7)	0.30428 (17)	0.0299 (3)
H11A	0.7020	0.2334	0.2338	0.036*
H11B	0.7432	0.2758	0.3631	0.036*
C12	0.70674 (18)	0.16036 (6)	0.40348 (16)	0.0277 (3)
H12	0.7894	0.1591	0.3541	0.033*
C13	0.6977 (2)	0.11098 (6)	0.48926 (16)	0.0291 (3)
C14	0.8217 (3)	0.06895 (8)	0.5020 (2)	0.0423 (4)
H14	0.9060	0.0724	0.4547	0.051*
C15	0.8215 (3)	0.02186 (8)	0.5846 (2)	0.0531 (5)
H15	0.9069	−0.0067	0.5942	0.064*
C16	0.6993 (3)	0.01612 (7)	0.6521 (2)	0.0471 (5)
H16	0.6997	−0.0165	0.7075	0.056*
C17	0.5745 (2)	0.05804 (7)	0.63967 (18)	0.0359 (3)
C18	0.5742 (2)	0.10550 (7)	0.55896 (17)	0.0307 (3)
H18	0.4900	0.1343	0.5511	0.037*
C19	0.3301 (3)	0.09082 (10)	0.7005 (2)	0.0532 (5)
H19A	0.3841	0.1279	0.7280	0.080*
H19B	0.2599	0.0807	0.7606	0.080*
H19C	0.2569	0.0927	0.6048	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.02571 (10)	0.02875 (10)	0.02277 (9)	−0.00058 (7)	0.00944 (7)	0.00156 (6)
S1	0.02396 (18)	0.0417 (2)	0.02944 (18)	−0.00463 (15)	0.00609 (14)	0.01091 (15)
O1	0.0427 (7)	0.0376 (6)	0.0521 (7)	−0.0008 (5)	0.0304 (6)	−0.0038 (5)
O2	0.0445 (7)	0.0437 (7)	0.0519 (8)	−0.0052 (6)	0.0118 (6)	0.0206 (6)
N1	0.0276 (6)	0.0381 (7)	0.0254 (6)	−0.0013 (5)	0.0084 (5)	−0.0009 (5)
N2	0.0246 (6)	0.0277 (6)	0.0243 (6)	0.0011 (5)	0.0103 (4)	0.0022 (4)
N3	0.0219 (6)	0.0267 (6)	0.0265 (6)	−0.0017 (4)	0.0097 (4)	−0.0012 (5)
C1	0.0207 (6)	0.0308 (7)	0.0267 (7)	−0.0019 (5)	0.0094 (5)	−0.0021 (5)
C2	0.0309 (7)	0.0231 (6)	0.0304 (7)	0.0032 (5)	0.0109 (6)	0.0021 (5)
C3	0.0325 (8)	0.0231 (6)	0.0310 (7)	0.0022 (5)	0.0127 (6)	−0.0001 (5)
C4	0.0332 (8)	0.0288 (7)	0.0286 (7)	0.0039 (6)	0.0127 (6)	0.0026 (6)
C5	0.0460 (10)	0.0326 (8)	0.0382 (9)	0.0058 (7)	0.0193 (7)	−0.0056 (7)
C6	0.0555 (12)	0.0295 (8)	0.0619 (12)	−0.0046 (8)	0.0238 (10)	−0.0167 (8)
C7	0.0429 (10)	0.0291 (8)	0.0558 (11)	−0.0066 (7)	0.0218 (8)	−0.0073 (7)
C8	0.0414 (10)	0.0485 (10)	0.0466 (10)	0.0115 (8)	0.0253 (8)	0.0059 (8)
C9	0.0289 (7)	0.0272 (7)	0.0308 (7)	0.0003 (5)	0.0122 (6)	0.0047 (6)
C10	0.0337 (8)	0.0311 (7)	0.0262 (7)	0.0027 (6)	0.0156 (6)	0.0025 (6)
C11	0.0282 (7)	0.0314 (7)	0.0349 (8)	−0.0005 (6)	0.0170 (6)	0.0022 (6)
C12	0.0218 (7)	0.0315 (7)	0.0310 (7)	−0.0002 (5)	0.0096 (5)	−0.0033 (6)
C13	0.0280 (7)	0.0268 (7)	0.0300 (7)	0.0022 (6)	0.0048 (6)	−0.0038 (6)
C14	0.0468 (10)	0.0380 (9)	0.0434 (10)	0.0151 (8)	0.0154 (8)	−0.0034 (7)
C15	0.0703 (14)	0.0342 (9)	0.0539 (11)	0.0251 (9)	0.0167 (10)	0.0000 (8)
C16	0.0649 (13)	0.0244 (7)	0.0448 (10)	0.0057 (8)	0.0052 (9)	0.0040 (7)
C17	0.0369 (9)	0.0293 (7)	0.0363 (8)	−0.0051 (6)	0.0026 (7)	0.0032 (6)
C18	0.0270 (7)	0.0266 (7)	0.0358 (8)	0.0002 (6)	0.0050 (6)	0.0030 (6)
C19	0.0392 (10)	0.0670 (13)	0.0561 (12)	−0.0005 (9)	0.0183 (9)	0.0273 (10)

Cu1—S1	2.3130 (4)	C14—C15	1.389 (2)
Cu1—N1i	1.9347 (12)	C15—C16	1.370 (3)
Cu1—N2	2.0917 (12)	C16—C17	1.394 (2)
Cu1—N3	2.0900 (13)	C17—C18	1.384 (2)
S1—C1	1.6542 (14)	C3—H3	0.950
O1—C4	1.363 (2)	C5—H5	0.950
O1—C8	1.425 (2)	C6—H6	0.950
O2—C17	1.364 (2)	C7—H7	0.950
O2—C19	1.424 (2)	C8—H8A	0.980
N1—C1	1.1505 (18)	C8—H8B	0.980
N2—C9	1.2665 (18)	C8—H8C	0.980
N2—C10	1.462 (2)	C9—H9	0.950
N3—C11	1.476 (2)	C10—H10A	0.990
N3—C12	1.2717 (18)	C10—H10B	0.990
C2—C3	1.386 (2)	C11—H11A	0.990
C2—C7	1.389 (2)	C11—H11B	0.990
C2—C9	1.471 (2)	C12—H12	0.950
C3—C4	1.390 (2)	C14—H14	0.950
C4—C5	1.389 (2)	C15—H15	0.950
C5—C6	1.388 (3)	C16—H16	0.950
C6—C7	1.380 (3)	C18—H18	0.950
C10—C11	1.515 (2)	C19—H19A	0.980
C12—C13	1.467 (2)	C19—H19B	0.980
C13—C14	1.390 (2)	C19—H19C	0.980
C13—C18	1.394 (2)
S1—Cu1—N1i	115.61 (4)	C4—C3—H3	119.9
S1—Cu1—N2	110.98 (3)	C4—C5—H5	120.6
S1—Cu1—N3	118.46 (3)	C6—C5—H5	120.6
N1i—Cu1—N2	110.48 (5)	C5—C6—H6	119.4
N1i—Cu1—N3	113.01 (5)	C7—C6—H6	119.4
N2—Cu1—N3	83.78 (4)	C2—C7—H7	120.1
Cu1—S1—C1	97.37 (5)	C6—C7—H7	120.1
C4—O1—C8	117.71 (13)	O1—C8—H8A	109.5
C17—O2—C19	117.00 (15)	O1—C8—H8B	109.5
Cu1ii—N1—C1	169.62 (13)	O1—C8—H8C	109.5
Cu1—N2—C9	131.98 (11)	H8A—C8—H8B	109.5
Cu1—N2—C10	107.01 (8)	H8A—C8—H8C	109.5
C9—N2—C10	118.26 (14)	H8B—C8—H8C	109.5
Cu1—N3—C11	107.88 (9)	N2—C9—H9	118.2
Cu1—N3—C12	136.32 (11)	C2—C9—H9	118.2
C11—N3—C12	115.52 (14)	N2—C10—H10A	109.8
S1—C1—N1	179.41 (15)	N2—C10—H10B	109.8
C3—C2—C7	119.65 (17)	C11—C10—H10A	109.8
C3—C2—C9	120.89 (13)	C11—C10—H10B	109.8
C7—C2—C9	119.31 (16)	H10A—C10—H10B	108.3
C2—C3—C4	120.22 (13)	N3—C11—H11A	109.6
O1—C4—C3	114.99 (12)	N3—C11—H11B	109.6
O1—C4—C5	124.75 (16)	C10—C11—H11A	109.6
C3—C4—C5	120.26 (16)	C10—C11—H11B	109.6
C4—C5—C6	118.86 (18)	H11A—C11—H11B	108.1
C5—C6—C7	121.14 (17)	N3—C12—H12	117.2
C2—C7—C6	119.77 (18)	C13—C12—H12	117.2
N2—C9—C2	123.57 (15)	C13—C14—H14	120.2
N2—C10—C11	109.21 (12)	C15—C14—H14	120.2
N3—C11—C10	110.28 (13)	C14—C15—H15	119.7
N3—C12—C13	125.68 (15)	C16—C15—H15	119.6
C12—C13—C14	117.15 (16)	C15—C16—H16	120.0
C12—C13—C18	123.00 (14)	C17—C16—H16	120.0
C14—C13—C18	119.84 (15)	C13—C18—H18	120.0
C13—C14—C15	119.6 (2)	C17—C18—H18	120.0
C14—C15—C16	120.70 (19)	O2—C19—H19A	109.5
C15—C16—C17	120.06 (17)	O2—C19—H19B	109.5
O2—C17—C16	115.76 (16)	O2—C19—H19C	109.5
O2—C17—C18	124.37 (15)	H19A—C19—H19B	109.5
C16—C17—C18	119.87 (18)	H19A—C19—H19C	109.5
C13—C18—C17	119.96 (15)	H19B—C19—H19C	109.5
C2—C3—H3	119.9
S1—Cu1—N1i—C1i	−141.8 (7)	C11—N3—C12—C13	176.20 (12)
N1i—Cu1—S1—C1	138.73 (7)	C12—N3—C11—C10	150.57 (12)
S1—Cu1—N2—C9	100.29 (12)	C3—C2—C7—C6	1.2 (2)
S1—Cu1—N2—C10	−99.44 (8)	C7—C2—C3—C4	1.8 (2)
N2—Cu1—S1—C1	11.92 (7)	C3—C2—C9—N2	−33.1 (2)
S1—Cu1—N3—C11	119.32 (7)	C9—C2—C3—C4	−173.74 (12)
S1—Cu1—N3—C12	−67.25 (13)	C7—C2—C9—N2	151.34 (14)
N3—Cu1—S1—C1	−82.44 (6)	C9—C2—C7—C6	176.78 (15)
N1i—Cu1—N2—C9	−29.30 (14)	C2—C3—C4—O1	175.86 (12)
N1i—Cu1—N2—C10	130.97 (8)	C2—C3—C4—C5	−3.0 (2)
N2—Cu1—N1i—C1i	−14.7 (7)	O1—C4—C5—C6	−177.52 (14)
N1i—Cu1—N3—C11	−100.84 (9)	C3—C4—C5—C6	1.3 (2)
N1i—Cu1—N3—C12	72.59 (14)	C4—C5—C6—C7	1.7 (2)
N3—Cu1—N1i—C1i	77.2 (7)	C5—C6—C7—C2	−3.0 (2)
N2—Cu1—N3—C11	8.80 (8)	N2—C10—C11—N3	52.70 (16)
N2—Cu1—N3—C12	−177.78 (13)	N3—C12—C13—C14	−173.84 (14)
N3—Cu1—N2—C9	−141.57 (13)	N3—C12—C13—C18	4.8 (2)
N3—Cu1—N2—C10	18.70 (8)	C12—C13—C14—C15	178.56 (15)
C8—O1—C4—C3	−171.75 (13)	C12—C13—C18—C17	−179.16 (13)
C8—O1—C4—C5	7.1 (2)	C14—C13—C18—C17	−0.6 (2)
C19—O2—C17—C16	−179.45 (15)	C18—C13—C14—C15	−0.1 (2)
C19—O2—C17—C18	1.5 (2)	C13—C14—C15—C16	0.7 (2)
Cu1—N2—C9—C2	−25.4 (2)	C14—C15—C16—C17	−0.7 (2)
Cu1—N2—C10—C11	−42.47 (13)	C15—C16—C17—O2	−179.10 (15)
C9—N2—C10—C11	120.98 (14)	C15—C16—C17—C18	−0.0 (2)
C10—N2—C9—C2	176.11 (11)	O2—C17—C18—C13	179.63 (14)
Cu1—N3—C11—C10	−34.46 (13)	C16—C17—C18—C13	0.6 (2)
Cu1—N3—C12—C13	3.1 (2)

Table 1

Selected bond lengths (Å)

Cu1—S1	2.3130 (4)
Cu1—N1i	1.9347 (12)
Cu1—N2	2.0917 (12)
Cu1—N3	2.0900 (13)

Symmetry code: (i) .