Iodido(1,10-phenanthroline-κN,N')(piperine-1-carbodithioato-κS,S')copper(II).

In the title compound, [Cu(C(6)H(10)NS(2))I(C(12)H(8)N(2))], the Cu(II) ion is coordinated by one iodide ion, two N atoms of the phenanthroline ligand and two S atoms from the piperidyl-dithio-carbamate ligand in a distorted square-pyramidal environment.

Related literature

For related literature, see: Englhardt et al. (1998 ▶); Fernández et al. (2000 ▶); Koh et al. (2003 ▶); Noro et al. (2000 ▶); Yaghi et al. (1998 ▶).

Experimental

Crystal data

[Cu(C6H10NS2)I(C12H8N2)]

M = 530.91

Monoclinic,

a = 6.408 (4) Å

b = 17.11 (1) Å

c = 18.400 (9) Å

β = 108.42 (2)°

V = 1914 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.98 mm−1

T = 293 (2) K

0.40 × 0.08 × 0.03 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku,2000 ▶) T min = 0.751, T max = 0.915

14752 measured reflections

4236 independent reflections

3298 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.166

S = 1.09

4236 reflections

226 parameters

H-atom parameters constrained

Δρmax = 1.41 e Å−3

Δρmin = −1.52 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028213/im2082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028213/im2082Isup2.hkl

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

[Cu(C6H10NS2)I(C12H8N2)]	F(000) = 1044
Mr = 530.91	Dx = 1.843 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4118 reflections
a = 6.408 (4) Å	θ = 3.3–27.5°
b = 17.11 (1) Å	µ = 2.98 mm−1
c = 18.400 (9) Å	T = 293 K
β = 108.42 (2)°	Prism, black
V = 1914 (2) Å3	0.40 × 0.08 × 0.03 mm
Z = 4

Rigaku Mercury CCD diffractometer	4236 independent reflections
Radiation source: Sealed Tube	3298 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.069
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku,2000)	h = −8→8
Tmin = 0.751, Tmax = 0.915	k = −22→22
14752 measured reflections	l = −23→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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0831P)2 + 0.6436P] where P = (Fo2 + 2Fc2)/3
4236 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 1.41 e Å−3
0 restraints	Δρmin = −1.52 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	0.45983 (13)	0.35695 (5)	0.41693 (4)	0.0396 (2)
I1	0.22830 (8)	0.21581 (3)	0.35611 (3)	0.04846 (19)
S1	0.2502 (3)	0.45295 (13)	0.33902 (11)	0.0603 (6)
S2	0.6695 (3)	0.39466 (10)	0.34223 (9)	0.0399 (4)
N1	0.4499 (9)	0.5001 (3)	0.2390 (3)	0.0405 (12)
N2	0.3528 (9)	0.3678 (3)	0.5106 (3)	0.0351 (11)
N3	0.6887 (9)	0.2896 (3)	0.4912 (3)	0.0361 (12)
C1	0.4559 (11)	0.4560 (3)	0.2983 (3)	0.0362 (14)
C2	0.2686 (13)	0.5527 (4)	0.2018 (4)	0.0539 (19)
H2A	0.3243	0.6054	0.2016	0.065*
H2B	0.1644	0.5533	0.2303	0.065*
C3	0.1534 (13)	0.5263 (4)	0.1201 (4)	0.0532 (18)
H3A	0.0410	0.5641	0.0947	0.064*
H3B	0.0819	0.4765	0.1207	0.064*
C4	0.3171 (14)	0.5182 (5)	0.0754 (4)	0.062 (2)
H4A	0.2430	0.4966	0.0251	0.074*
H4B	0.3735	0.5694	0.0685	0.074*
C5	0.5064 (13)	0.4654 (5)	0.1179 (4)	0.059 (2)
H5A	0.6141	0.4637	0.0909	0.071*
H5B	0.4522	0.4127	0.1197	0.071*
C6	0.6142 (12)	0.4953 (4)	0.1989 (4)	0.0492 (17)
H6A	0.7317	0.4602	0.2262	0.059*
H6B	0.6774	0.5465	0.1973	0.059*
C7	0.1837 (11)	0.4078 (3)	0.5183 (4)	0.0411 (15)
H7A	0.1003	0.4386	0.4778	0.049*
C8	0.1278 (12)	0.4048 (4)	0.5863 (4)	0.0472 (17)
H8A	0.0098	0.4340	0.5905	0.057*
C9	0.2441 (12)	0.3598 (4)	0.6453 (4)	0.0436 (16)
H9A	0.2049	0.3568	0.6898	0.052*
C10	0.4269 (12)	0.3172 (4)	0.6389 (4)	0.0399 (15)
C11	0.4745 (10)	0.3239 (3)	0.5700 (3)	0.0328 (13)
C12	0.5573 (13)	0.2666 (4)	0.6979 (4)	0.0483 (17)
H12A	0.5235	0.2607	0.7432	0.058*
C13	0.7278 (13)	0.2278 (4)	0.6880 (4)	0.0478 (17)
H13A	0.8131	0.1963	0.7275	0.057*
C14	0.7832 (11)	0.2334 (4)	0.6183 (4)	0.0416 (15)
C15	0.6546 (11)	0.2818 (3)	0.5602 (4)	0.0343 (13)
C16	0.9566 (13)	0.1938 (4)	0.6047 (4)	0.0488 (17)
H16A	1.0493	0.1625	0.6426	0.059*
C17	0.9907 (12)	0.2009 (4)	0.5348 (4)	0.0463 (16)
H17A	1.1035	0.1734	0.5246	0.056*
C18	0.8542 (11)	0.2500 (4)	0.4793 (4)	0.0408 (14)
H18A	0.8795	0.2552	0.4325	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.0419 (5)	0.0493 (5)	0.0317 (4)	0.0084 (3)	0.0172 (4)	0.0075 (3)
I1	0.0453 (3)	0.0554 (3)	0.0486 (3)	−0.0062 (2)	0.0204 (2)	−0.01413 (19)
S1	0.0582 (13)	0.0803 (13)	0.0535 (11)	0.0306 (10)	0.0335 (10)	0.0285 (10)
S2	0.0402 (9)	0.0471 (9)	0.0349 (8)	0.0043 (7)	0.0155 (7)	0.0071 (6)
N1	0.046 (3)	0.046 (3)	0.032 (3)	0.005 (2)	0.015 (3)	0.011 (2)
N2	0.038 (3)	0.038 (3)	0.028 (3)	0.000 (2)	0.010 (2)	−0.001 (2)
N3	0.035 (3)	0.043 (3)	0.032 (3)	0.001 (2)	0.012 (2)	0.000 (2)
C1	0.042 (4)	0.039 (3)	0.027 (3)	0.001 (3)	0.010 (3)	0.001 (2)
C2	0.068 (5)	0.045 (4)	0.042 (4)	0.014 (4)	0.010 (4)	0.009 (3)
C3	0.055 (5)	0.041 (4)	0.052 (4)	0.003 (3)	−0.001 (4)	0.004 (3)
C4	0.071 (6)	0.076 (5)	0.030 (4)	0.002 (4)	0.002 (4)	−0.001 (3)
C5	0.058 (5)	0.079 (5)	0.045 (4)	0.009 (4)	0.022 (4)	0.005 (4)
C6	0.045 (4)	0.060 (4)	0.041 (4)	0.001 (3)	0.011 (3)	0.018 (3)
C7	0.046 (4)	0.038 (3)	0.044 (4)	0.010 (3)	0.021 (3)	0.001 (3)
C8	0.051 (4)	0.050 (4)	0.051 (4)	0.001 (3)	0.029 (4)	−0.007 (3)
C9	0.058 (5)	0.042 (3)	0.037 (4)	−0.010 (3)	0.023 (4)	−0.011 (3)
C10	0.046 (4)	0.044 (3)	0.034 (3)	−0.009 (3)	0.019 (3)	−0.003 (3)
C11	0.036 (4)	0.032 (3)	0.029 (3)	−0.009 (2)	0.008 (3)	0.000 (2)
C12	0.059 (5)	0.056 (4)	0.031 (3)	−0.009 (3)	0.016 (3)	0.001 (3)
C13	0.055 (5)	0.050 (4)	0.034 (4)	−0.008 (3)	0.006 (3)	0.008 (3)
C14	0.039 (4)	0.041 (3)	0.040 (4)	−0.005 (3)	0.006 (3)	0.005 (3)
C15	0.037 (4)	0.033 (3)	0.033 (3)	−0.001 (2)	0.012 (3)	−0.001 (2)
C16	0.049 (5)	0.040 (3)	0.052 (4)	0.003 (3)	0.010 (4)	0.006 (3)
C17	0.034 (4)	0.046 (4)	0.058 (5)	0.006 (3)	0.012 (3)	−0.003 (3)
C18	0.035 (4)	0.046 (3)	0.043 (4)	0.002 (3)	0.014 (3)	−0.002 (3)

Cu1—N3	2.020 (5)	C5—H5A	0.9700
Cu1—N2	2.055 (5)	C5—H5B	0.9700
Cu1—S2	2.2972 (19)	C6—H6A	0.9700
Cu1—S1	2.311 (2)	C6—H6B	0.9700
Cu1—I1	2.8694 (16)	C7—C8	1.408 (8)
S1—C1	1.711 (6)	C7—H7A	0.9300
S2—C1	1.711 (7)	C8—C9	1.348 (10)
N1—C1	1.317 (7)	C8—H8A	0.9300
N1—C2	1.457 (9)	C9—C10	1.416 (10)
N1—C6	1.466 (8)	C9—H9A	0.9300
N2—C7	1.326 (8)	C10—C11	1.398 (8)
N2—C11	1.353 (8)	C10—C12	1.433 (10)
N3—C18	1.334 (8)	C11—C15	1.419 (9)
N3—C15	1.361 (7)	C12—C13	1.339 (11)
C2—C3	1.520 (10)	C12—H12A	0.9300
C2—H2A	0.9700	C13—C14	1.438 (10)
C2—H2B	0.9700	C13—H13A	0.9300
C3—C4	1.530 (11)	C14—C16	1.391 (10)
C3—H3A	0.9700	C14—C15	1.397 (9)
C3—H3B	0.9700	C16—C17	1.376 (10)
C4—C5	1.517 (11)	C16—H16A	0.9300
C4—H4A	0.9700	C17—C18	1.395 (10)
C4—H4B	0.9700	C17—H17A	0.9300
C5—C6	1.520 (10)	C18—H18A	0.9300
N3—Cu1—N2	81.2 (2)	C4—C5—H5B	109.6
N3—Cu1—S2	97.36 (16)	C6—C5—H5B	109.6
N2—Cu1—S2	152.84 (15)	H5A—C5—H5B	108.1
N3—Cu1—S1	168.73 (16)	N1—C6—C5	109.6 (6)
N2—Cu1—S1	99.97 (15)	N1—C6—H6A	109.7
S2—Cu1—S1	76.38 (7)	C5—C6—H6A	109.7
N3—Cu1—I1	87.66 (15)	N1—C6—H6B	109.7
N2—Cu1—I1	97.75 (14)	C5—C6—H6B	109.7
S2—Cu1—I1	109.33 (6)	H6A—C6—H6B	108.2
S1—Cu1—I1	103.21 (8)	N2—C7—C8	121.5 (6)
C1—S1—Cu1	85.2 (2)	N2—C7—H7A	119.3
C1—S2—Cu1	85.6 (2)	C8—C7—H7A	119.3
C1—N1—C2	123.5 (6)	C9—C8—C7	120.4 (6)
C1—N1—C6	123.1 (5)	C9—C8—H8A	119.8
C2—N1—C6	113.1 (5)	C7—C8—H8A	119.8
C7—N2—C11	118.8 (5)	C8—C9—C10	119.2 (6)
C7—N2—Cu1	129.5 (4)	C8—C9—H9A	120.4
C11—N2—Cu1	111.6 (4)	C10—C9—H9A	120.4
C18—N3—C15	118.3 (6)	C11—C10—C9	117.2 (6)
C18—N3—Cu1	128.6 (4)	C11—C10—C12	119.6 (6)
C15—N3—Cu1	113.0 (4)	C9—C10—C12	123.2 (6)
N1—C1—S1	123.8 (5)	N2—C11—C10	122.9 (6)
N1—C1—S2	123.5 (5)	N2—C11—C15	117.6 (5)
S1—C1—S2	112.7 (3)	C10—C11—C15	119.6 (6)
N1—C2—C3	110.3 (6)	C13—C12—C10	120.1 (6)
N1—C2—H2A	109.6	C13—C12—H12A	120.0
C3—C2—H2A	109.6	C10—C12—H12A	120.0
N1—C2—H2B	109.6	C12—C13—C14	122.1 (7)
C3—C2—H2B	109.6	C12—C13—H13A	119.0
H2A—C2—H2B	108.1	C14—C13—H13A	119.0
C2—C3—C4	111.0 (7)	C16—C14—C15	117.5 (6)
C2—C3—H3A	109.4	C16—C14—C13	124.4 (7)
C4—C3—H3A	109.4	C15—C14—C13	118.0 (7)
C2—C3—H3B	109.4	N3—C15—C14	122.8 (6)
C4—C3—H3B	109.4	N3—C15—C11	116.5 (5)
H3A—C3—H3B	108.0	C14—C15—C11	120.6 (6)
C5—C4—C3	110.5 (6)	C17—C16—C14	119.8 (7)
C5—C4—H4A	109.6	C17—C16—H16A	120.1
C3—C4—H4A	109.6	C14—C16—H16A	120.1
C5—C4—H4B	109.6	C16—C17—C18	119.3 (6)
C3—C4—H4B	109.6	C16—C17—H17A	120.4
H4A—C4—H4B	108.1	C18—C17—H17A	120.4
C4—C5—C6	110.3 (6)	N3—C18—C17	122.2 (6)
C4—C5—H5A	109.6	N3—C18—H18A	118.9
C6—C5—H5A	109.6	C17—C18—H18A	118.9