Literature DB >> 22807770

Bis[2-(5-methyl-sulfanyl-1,3,4-oxadiazol-2-yl-κN(3))phenolato-κO(1)]copper(II).

Souheila Ouilia, Chahrazed Beghidja, Adel Beghidja, François Michaud.

Abstract

In the title complex, [Cu(C(9)H(7)N(2)O(2)S)(2)], the Cu(II) ion, located on an inversion center, adopts an N(2)O(2) square-planar coord-ination. The 2-(5-methyl-sulfanyl-1,3,4-oxadiazol-2-yl)phenolate ligand is chelated to the central Cu(II) ion in an N,O-bidentate manner.

Entities: CellLine Chemical Disease Species

Year: 2012 PMID： 22807770 PMCID： PMC3393202 DOI： 10.1107/S1600536812026815

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For general background to derivatives of dithiocarbazate ligands and their metal complexes, see: Beghidja et al. (2005 ▶; 2006 ▶); Bouchameni et al. (2011 ▶); Beghidja, Bouslimani & Welter (2007 ▶); Beghidja, Rogez & Welter (2007 ▶). For similar structures, see: Kala et al. (2007 ▶); Liu et al. (2008 ▶); Zhang et al. (2001 ▶). For the preparation of the ligand, see: Dolman et al. (2006 ▶); Young & Wood (1955 ▶).

Experimental

Crystal data

[Cu(C9H7N2O2S)2] M = 478.02 Monoclinic, a = 12.5695 (7) Å b = 4.4216 (3) Å c = 17.3861 (9) Å β = 106.005 (6)° V = 928.81 (9) Å3 Z = 2 Mo Kα radiation μ = 1.44 mm−1 T = 170 K 0.18 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.926, T max = 1.000 6693 measured reflections 1906 independent reflections 1250 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.066 S = 0.99 1906 reflections 133 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.18 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026815/hp2039sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026815/hp2039Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C₉H₇N₂O₂S)₂]	F(000) = 486
M_r = 478.02	Least Squares Treatment of 25 SET4 setting angles.
Monoclinic, P2₁/n	D_x = 1.709 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5695 (7) Å	Cell parameters from 2354 reflections
b = 4.4216 (3) Å	θ = 3.3–31.6°
c = 17.3861 (9) Å	µ = 1.44 mm⁻¹
β = 106.005 (6)°	T = 170 K
V = 928.81 (9) Å³	Plates, green
Z = 2	0.18 × 0.12 × 0.09 mm

Oxford Diffraction Xcalibur CCD diffractometer	1906 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1250 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 18.4 pixels mm^-1	θ_max = 26.4°, θ_min = 3.4°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −5→5
T_min = 0.926, T_max = 1.000	l = −21→14
6693 measured 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0283P)²] where P = (F_o² + 2F_c²)/3
1906 reflections	(Δ/σ)_max = 0.004
133 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	U_iso*/U_eq
Cu1	0.50000	0.00000	1.00000	0.0381 (1)
S1	0.45296 (6)	0.47186 (17)	0.68566 (4)	0.0455 (3)
O1	0.58495 (13)	0.1114 (4)	0.79047 (9)	0.0362 (6)
O2	0.62190 (14)	−0.2686 (5)	1.01766 (9)	0.0506 (7)
N1	0.51554 (16)	0.0936 (5)	0.89257 (11)	0.0347 (7)
N2	0.44837 (16)	0.2890 (5)	0.83525 (11)	0.0387 (8)
C1	0.59434 (18)	−0.0065 (6)	0.86434 (13)	0.0315 (7)
C2	0.68113 (19)	−0.2153 (6)	0.89831 (14)	0.0326 (8)
C3	0.68883 (19)	−0.3359 (6)	0.97479 (15)	0.0356 (8)
C4	0.7755 (2)	−0.5413 (6)	1.00571 (15)	0.0424 (9)
C5	0.8503 (2)	−0.6167 (6)	0.96422 (17)	0.0474 (10)
C6	0.8424 (2)	−0.4940 (7)	0.88955 (16)	0.0455 (9)
C7	0.7584 (2)	−0.2969 (6)	0.85724 (16)	0.0429 (10)
C8	0.4933 (2)	0.2903 (6)	0.77720 (14)	0.0346 (8)
C9	0.3251 (2)	0.6276 (7)	0.69352 (17)	0.0602 (11)
H4	0.78230	−0.62840	1.05550	0.0510*
H5	0.90710	−0.75200	0.98660	0.0570*
H6	0.89350	−0.54500	0.86190	0.0550*
H7	0.75220	−0.21510	0.80690	0.0510*
H9A	0.29080	0.74020	0.64590	0.0900*
H9B	0.33910	0.75940	0.73910	0.0900*
H9C	0.27680	0.46690	0.69980	0.0900*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0309 (2)	0.0596 (3)	0.0265 (2)	0.0096 (2)	0.0123 (2)	0.0020 (3)
S1	0.0469 (4)	0.0576 (5)	0.0340 (4)	−0.0015 (4)	0.0146 (3)	0.0092 (4)
O1	0.0361 (10)	0.0457 (11)	0.0307 (9)	−0.0003 (8)	0.0158 (8)	0.0006 (8)
O2	0.0442 (11)	0.0785 (14)	0.0346 (10)	0.0221 (10)	0.0200 (9)	0.0092 (11)
N1	0.0300 (11)	0.0482 (14)	0.0274 (11)	0.0054 (10)	0.0104 (9)	0.0020 (10)
N2	0.0340 (12)	0.0521 (15)	0.0303 (12)	0.0051 (11)	0.0093 (10)	0.0039 (11)
C1	0.0301 (12)	0.0398 (14)	0.0261 (12)	−0.0068 (14)	0.0102 (10)	−0.0058 (14)
C2	0.0285 (13)	0.0385 (15)	0.0316 (13)	−0.0021 (11)	0.0098 (11)	−0.0059 (12)
C3	0.0289 (13)	0.0443 (16)	0.0341 (14)	−0.0017 (12)	0.0095 (11)	−0.0084 (13)
C4	0.0397 (15)	0.0520 (19)	0.0342 (13)	0.0079 (13)	0.0078 (12)	0.0011 (14)
C5	0.0398 (16)	0.0462 (17)	0.0562 (19)	0.0112 (13)	0.0135 (14)	−0.0070 (15)
C6	0.0398 (14)	0.0508 (17)	0.0535 (16)	0.0065 (15)	0.0256 (13)	−0.0016 (17)
C7	0.0426 (16)	0.0489 (18)	0.0438 (16)	0.0004 (14)	0.0230 (13)	−0.0031 (14)
C8	0.0320 (14)	0.0401 (16)	0.0315 (14)	−0.0036 (12)	0.0086 (12)	−0.0033 (12)
C9	0.060 (2)	0.069 (2)	0.0527 (19)	0.0110 (16)	0.0175 (16)	0.0157 (16)

Cu1—O2	1.896 (2)	C2—C3	1.411 (3)
Cu1—N1	1.9746 (19)	C2—C7	1.402 (4)
Cu1—O2ⁱ	1.896 (2)	C3—C4	1.406 (4)
Cu1—N1ⁱ	1.9746 (19)	C4—C5	1.375 (4)
S1—C8	1.729 (3)	C5—C6	1.385 (4)
S1—C9	1.788 (3)	C6—C7	1.365 (4)
O1—C1	1.361 (3)	C4—H4	0.9300
O1—C8	1.364 (3)	C5—H5	0.9300
O2—C3	1.303 (3)	C6—H6	0.9300
N1—N2	1.410 (3)	C7—H7	0.9300
N1—C1	1.298 (3)	C9—H9A	0.9600
N2—C8	1.285 (3)	C9—H9B	0.9600
C1—C2	1.427 (4)	C9—H9C	0.9600

Cu1···O2ⁱⁱ	3.555 (2)	C3···Cu1^vi	3.876 (3)
Cu1···C3ⁱⁱ	3.876 (3)	C3···N1^vi	3.381 (3)
Cu1···C4ⁱⁱ	3.991 (3)	C3···C1^vi	3.554 (4)
Cu1···O2ⁱⁱⁱ	3.555 (2)	C3···Cu1ⁱⁱⁱ	3.876 (3)
Cu1···C3ⁱⁱⁱ	3.876 (3)	C4···C2^vi	3.543 (4)
Cu1···C4ⁱⁱⁱ	3.991 (3)	C4···Cu1^vi	3.991 (3)
S1···H6^iv	3.1400	C4···C1^vi	3.517 (4)
S1···H4^v	3.0600	C4···Cu1ⁱⁱⁱ	3.991 (3)
O1···N2	2.215 (3)	C5···C7^vi	3.557 (4)
O1···C7ⁱⁱ	3.399 (3)	C5···C2^vi	3.391 (4)
O2···N2ⁱ	2.928 (3)	C7···O1^vi	3.399 (3)
O2···C1	2.839 (3)	C7···C5ⁱⁱ	3.557 (4)
O2···Cu1^vi	3.555 (2)	C8···C1ⁱⁱ	3.538 (4)
O2···N1	2.735 (3)	C8···C2ⁱⁱ	3.471 (4)
O2···Cu1ⁱⁱⁱ	3.555 (2)	C9···N2^x	3.410 (3)
O2···N1ⁱ	2.740 (3)	C3···H9A^viii	2.9300
O1···H6^vii	2.8200	C4···H9A^viii	2.7400
O1···H7	2.5000	C8···H9B^vi	3.0000
O2···H9A^viii	2.6200	C9···H9C^x	2.9400
N1···O1	2.185 (3)	H4···S1^xi	3.0600
N1···O2	2.735 (3)	H4···H9A^viii	2.3100
N1···C3	2.946 (3)	H6···S1^xii	3.1400
N1···C3ⁱⁱ	3.381 (3)	H6···O1^xiii	2.8200
N1···O2ⁱ	2.740 (3)	H7···O1	2.5000
N2···O1	2.215 (3)	H9A···O2^xiv	2.6200
N2···O2ⁱ	2.928 (3)	H9A···C3^xiv	2.9300
N2···C9^ix	3.410 (3)	H9A···C4^xiv	2.7400
N2···H9C	2.8300	H9A···H4^xiv	2.3100
N2···H9B	2.7800	H9B···N2	2.7800
C1···C3ⁱⁱ	3.554 (4)	H9B···C8ⁱⁱ	3.0000
C1···C4ⁱⁱ	3.517 (4)	H9B···H9C^x	2.2200
C1···C8^vi	3.538 (4)	H9C···N2	2.8300
C2···C4ⁱⁱ	3.543 (4)	H9C···C9^ix	2.9400
C2···C5ⁱⁱ	3.391 (4)	H9C···H9B^ix	2.2200
C2···C8^vi	3.471 (4)

O2—Cu1—N1	89.90 (8)	C3—C4—C5	121.7 (2)
O2—Cu1—O2ⁱ	180.00	C4—C5—C6	121.0 (2)
O2—Cu1—N1ⁱ	90.11 (8)	C5—C6—C7	118.9 (2)
O2ⁱ—Cu1—N1	90.11 (8)	C2—C7—C6	121.4 (2)
N1—Cu1—N1ⁱ	180.00	S1—C8—O1	116.41 (17)
O2ⁱ—Cu1—N1ⁱ	89.90 (8)	S1—C8—N2	130.1 (2)
C8—S1—C9	98.63 (13)	O1—C8—N2	113.5 (2)
C1—O1—C8	103.37 (18)	C3—C4—H4	119.00
Cu1—O2—C3	132.15 (16)	C5—C4—H4	119.00
Cu1—N1—N2	126.93 (15)	C4—C5—H5	120.00
Cu1—N1—C1	124.81 (17)	C6—C5—H5	119.00
N2—N1—C1	108.19 (19)	C5—C6—H6	121.00
N1—N2—C8	104.5 (2)	C7—C6—H6	121.00
O1—C1—N1	110.5 (2)	C2—C7—H7	119.00
O1—C1—C2	119.7 (2)	C6—C7—H7	119.00
N1—C1—C2	129.8 (2)	S1—C9—H9A	109.00
C1—C2—C3	118.7 (2)	S1—C9—H9B	109.00
C1—C2—C7	120.9 (2)	S1—C9—H9C	109.00
C3—C2—C7	120.4 (2)	H9A—C9—H9B	109.00
O2—C3—C2	124.4 (2)	H9A—C9—H9C	110.00
O2—C3—C4	118.9 (2)	H9B—C9—H9C	109.00
C2—C3—C4	116.7 (2)

N1—Cu1—O2—C3	3.7 (2)	Cu1—N1—C1—O1	−176.81 (15)
N1ⁱ—Cu1—O2—C3	−176.3 (2)	N1—N2—C8—O1	0.2 (3)
O2—Cu1—N1—N2	178.6 (2)	N1—N2—C8—S1	177.9 (2)
O2ⁱ—Cu1—N1—N2	−1.4 (2)	O1—C1—C2—C7	1.2 (4)
O2—Cu1—N1—C1	−4.9 (2)	N1—C1—C2—C7	179.4 (3)
O2ⁱ—Cu1—N1—C1	175.1 (2)	O1—C1—C2—C3	−179.6 (2)
C9—S1—C8—O1	173.0 (2)	N1—C1—C2—C3	−1.4 (4)
C9—S1—C8—N2	−4.7 (3)	C3—C2—C7—C6	0.2 (4)
C8—O1—C1—N1	−0.1 (3)	C1—C2—C3—C4	179.8 (2)
C1—O1—C8—N2	−0.1 (3)	C1—C2—C7—C6	179.3 (3)
C8—O1—C1—C2	178.4 (2)	C1—C2—C3—O2	−0.4 (4)
C1—O1—C8—S1	−178.12 (18)	C7—C2—C3—O2	178.8 (2)
Cu1—O2—C3—C2	−1.8 (4)	C7—C2—C3—C4	−1.0 (4)
Cu1—O2—C3—C4	177.95 (18)	O2—C3—C4—C5	−178.6 (2)
C1—N1—N2—C8	−0.3 (3)	C2—C3—C4—C5	1.2 (4)
Cu1—N1—N2—C8	176.71 (18)	C3—C4—C5—C6	−0.5 (4)
N2—N1—C1—C2	−178.1 (3)	C4—C5—C6—C7	−0.3 (4)
N2—N1—C1—O1	0.2 (3)	C5—C6—C7—C2	0.5 (4)
Cu1—N1—C1—C2	4.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.50	2.822 (3)	100

Table 1

Selected bond lengths (Å)

Cu1—O2	1.896 (2)
Cu1—N1	1.9746 (19)

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